#------------------------------------------------------------------------------
#$Date: 2021-05-07 08:38:59 +0300 (Fri, 07 May 2021) $
#$Revision: 265041 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/23/2022374.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2022374
loop_
_publ_author_name
'Roy, Monalisa'
'Li, Keyao'
'Nisar, Madiha'
'Wong, Lawrence W.-Y.'
'Sung, Herman H.-Y.'
'Haynes, Richard K.'
'Williams, Ian D.'
_publ_section_title
;
Varying degrees of homostructurality in a series of cocrystals of
antimalarial drug 11-azaartemisinin with salicylic acids
;
_journal_coeditor_code DV3004
_journal_issue 6
_journal_name_full 'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi 10.1107/S2053229621004460
_journal_volume 77
_journal_year 2021
_chemical_absolute_configuration rmad
_chemical_formula_iupac 'C15 H23 N O4, C7 H4 Br2 O3'
_chemical_formula_moiety 'C15 H23 N O4, C7 H4 Br2 O3'
_chemical_formula_sum 'C22 H27 Br2 N O7'
_chemical_formula_weight 577.26
_chemical_name_common
;
11-Azaartemisinin--3,5-bromosalicylic acid (1/1)
;
_chemical_name_systematic
'1,5,9-Trimethyl-14,15,16-trioxa-11-azatetracyclo[10.3.1.0^4,13^.0^8,13^]hexadecan-10-one; 3,5-dibromosalicylic acid'
_space_group_crystal_system monoclinic
_space_group_IT_number 4
_space_group_name_Hall 'P 2yb'
_space_group_name_H-M_alt 'P 1 21 1'
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary direct
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha 90
_cell_angle_beta 99.6446(19)
_cell_angle_gamma 90
_cell_formula_units_Z 2
_cell_length_a 9.52200(19)
_cell_length_b 9.3214(2)
_cell_length_c 13.3453(3)
_cell_measurement_reflns_used 3893
_cell_measurement_temperature 100.01(10)
_cell_measurement_theta_max 72.4230
_cell_measurement_theta_min 3.3420
_cell_volume 1167.77(4)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2020)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2020)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2020)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS1986 (Sheldrick, 2008)
;
_diffrn_ambient_temperature 100.01(10)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 5.1788
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device 'kappa diffractometer'
_diffrn_measurement_device_type
'Rigaku OD SuperNova Dual source diffractometer with an Atlas detector'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_monochromator mirror
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_reflns_av_R_equivalents 0.0279
_diffrn_reflns_av_unetI/netI 0.0458
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_number 6899
_diffrn_reflns_theta_full 67.684
_diffrn_reflns_theta_max 72.312
_diffrn_reflns_theta_min 3.359
_diffrn_source 'micro-focus sealed X-ray tube'
_diffrn_source_current 0.80
_diffrn_source_power 0.040
_diffrn_source_voltage 50
_exptl_absorpt_coefficient_mu 4.778
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.97683
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2020)
;
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.642
_exptl_crystal_description block
_exptl_crystal_F_000 584
_exptl_crystal_size_max 0.05
_exptl_crystal_size_mid 0.05
_exptl_crystal_size_min 0.04
_refine_diff_density_max 0.266
_refine_diff_density_min -0.443
_refine_ls_abs_structure_details
;
Flack x determined using 1437 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack -0.034(19)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.034
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 304
_refine_ls_number_reflns 4060
_refine_ls_number_restraints 2
_refine_ls_restrained_S_all 1.034
_refine_ls_R_factor_all 0.0330
_refine_ls_R_factor_gt 0.0297
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0219P)^2^+0.1825P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0646
_refine_ls_wR_factor_ref 0.0665
_reflns_number_gt 3811
_reflns_number_total 4060
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file dv3004sup1.cif
_cod_data_source_block mona22cult
_cod_original_cell_volume 1167.76(4)
_cod_database_code 2022374
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_hkl_file
;
0 -11 0-378.265 290.224 6
0 -11 1 1776.32 431.222 6
0 -11 -1 1919.21 407.977 6
0 -11 2 3211.68 512.934 6
0 -11 -2 2051.71 345.996 6
0 -11 3 7925.83 686.634 6
0 -11 4 16039.2 822.992 6
0 -10 0 7803.23 991.186 6
0 -10 1 2294.53 649.120 6
0 -10 -1 3221.60 709.808 6
0 -10 1 2600.75 443.589 8
0 -10 2 19301.9 1513.25 6
0 -10 -2 20789.7 1437.36 6
0 -10 2 18178.9 1254.04 8
0 -10 -3 1426.68 421.601 6
0 -10 3 979.650 441.893 8
0 -10 3 696.464 460.795 6
0 -10 -3 425.997 233.217 9
0 -10 4 5038.72 722.176 6
0 -10 4 5820.76 762.716 8
0 -10 -4 4685.65 606.742 9
0 -10 -4 5108.25 593.153 6
0 -10 5 1767.00 506.317 8
0 -10 -5 1389.04 412.605 9
0 -10 5 598.981 325.127 6
0 -10 -6 731.617 303.074 9
0 -10 6 618.760 255.703 6
0 -10 6 492.044 328.487 8
0 -10 -7 1898.19 378.189 9
0 -10 7 1418.01 405.401 8
0 -10 8 10787.0 687.772 8
0 -9 0-762.196 278.530 8
0 -9 -1 9588.92 1210.01 6
0 -9 1 8011.20 952.926 8
0 -9 -2 3863.23 778.463 6
0 -9 2 3880.14 740.553 8
0 -9 -3 27909.0 1756.90 6
0 -9 3 26411.3 1850.21 8
0 -9 4 10318.2 1199.79 6
0 -9 4 11871.8 1296.38 8
0 -9 -4 11454.8 1077.71 6
0 -9 5 10963.3 1133.09 6
0 -9 5 9853.51 1202.98 8
0 -9 -6 8840.21 1012.55 9
0 -9 6 7829.49 1085.52 8
0 -9 6 8878.92 934.451 6
0 -9 -7 1579.58 517.589 9
0 -9 7 1269.94 547.063 8
0 -9 -8 6461.84 776.732 9
0 -9 8 6289.58 799.199 8
0 -9 -9 4819.68 596.468 9
0 -9 9 5433.18 639.316 8
0 -9 -10 9023.61 636.293 9
0 -8 -3 818.749 390.787 6
0 -8 -4 18859.9 1416.69 6
0 -8 5 15256.5 1553.85 8
0 -8 6 782.208 606.233 8
0 -8 7 10791.1 1269.49 8
0 -8 8 13050.0 1354.17 8
0 -8 -8 13866.8 1346.34 9
0 -8 9 11104.8 1107.63 8
0 -8 -9 10756.4 1101.30 9
0 -8 -10 8212.23 840.761 9
0 -8 10 7921.39 806.665 8
0 -8 -11 6429.12 605.882 9
0 -8 11 5501.99 481.068 8
0 -7 0 581.436 722.030 2
0 -7 -1 15698.7 1615.05 2
0 -7 1 15782.9 1856.75 2
0 -7 2 2892.85 991.406 2
0 -7 2 1122.15 739.988 3
0 -7 3 43292.0 3248.04 3
0 -7 4 15405.0 1930.28 3
0 -7 -4 12477.5 1077.18 6
0 -7 -5 16611.8 1575.17 5
0 -7 5 13287.6 1727.03 3
0 -7 6 6547.98 1036.29 8
0 -7 -6 6276.77 1061.51 5
0 -7 7 2142.41 744.126 8
0 -7 -7 2339.59 749.406 5
0 -7 8 804.042 598.631 8
0 -7 -8 239.075 626.545 5
0 -7 9 3833.40 797.534 8
0 -7 -9 3604.07 819.795 5
0 -7 -9 4066.57 803.124 9
0 -7 -10 21751.6 1708.96 5
0 -7 -10 23056.8 1598.34 9
0 -7 10 22419.1 1500.45 8
0 -7 11 6696.57 708.628 8
0 -7 -11 6576.09 771.271 9
0 -7 -11 5666.99 833.974 5
0 -7 -12 6931.38 608.432 9
0 -6 0 159026. 5099.18 2
0 -6 -1 54900.0 2963.50 2
0 -6 -1 58862.5 2756.26 4
0 -6 1 62643.8 3388.23 2
0 -6 1 60688.1 3504.45 3
0 -6 -2 40854.5 2448.34 2
0 -6 2 38849.8 2822.71 3
0 -6 3 10104.8 1479.83 3
0 -6 4 10241.5 1530.39 3
0 -6 -4 9891.95 1072.66 5
0 -6 -5 20424.8 1553.59 5
0 -6 5 18937.6 2040.09 3
0 -6 6 13794.6 1808.77 3
0 -6 -6 13296.2 1357.52 5
0 -6 7 24306.5 1783.58 8
0 -6 -7 24445.9 1909.10 5
0 -6 7 26455.2 2330.41 3
0 -6 -8 53468.0 2839.65 5
0 -6 8 51165.2 2581.85 8
0 -6 -9 31581.7 2022.06 9
0 -6 9 33218.5 2024.11 8
0 -6 -9 34385.0 2327.39 5
0 -6 -10 39926.8 2445.30 5
0 -6 10 37544.2 1991.03 8
0 -6 -10 39113.2 2164.27 9
0 -6 -11 9137.53 1199.03 5
0 -6 -11 8897.84 972.937 9
0 -6 11 9720.71 920.718 8
0 -6 -12 2498.38 626.013 5
0 -6 -12 2198.96 442.625 9
0 -6 -13 3736.85 552.810 5
0 -5 0-478.898 695.231 3
0 -5 0 144.301 511.091 2
0 -5 -1 29911.3 1969.89 2
0 -5 1 28128.8 2182.41 3
0 -5 -2 20024.5 1414.07 4
0 -5 2 22467.0 1968.34 3
0 -5 -2 21072.6 1594.37 2
0 -5 -3 2826.20 560.046 4
0 -5 -3 2434.25 614.492 2
0 -5 4 18742.8 1853.53 3
0 -5 5 33764.0 2541.70 3
0 -5 -6 7267.43 918.306 5
0 -5 6 3809.58 975.702 3
0 -5 -7 866.257 620.739 5
0 -5 7 1183.90 587.872 8
0 -5 7 1700.46 713.420 3
0 -5 8 1840.84 503.070 8
0 -5 -8 1592.45 674.115 5
0 -5 9 5573.07 862.791 8
0 -5 -9 5187.72 973.377 5
0 -5 10 9067.17 999.981 8
0 -5 -10 9487.18 1096.06 9
0 -5 -10 7970.67 1238.71 5
0 -5 -11 22837.6 1515.30 9
0 -5 -11 21918.2 1895.53 5
0 -5 -12 13249.1 1036.54 9
0 -5 -12 9969.67 1219.08 5
0 -5 -13 9296.91 1035.12 5
0 -5 -14 517.439 313.421 5
0 -4 0 174905. 4601.84 3
0 -4 -1 344674. 5749.41 2
0 -4 1 338516. 6307.86 3
0 -4 2 149097. 4241.14 3
0 -4 -2 153247. 3685.22 2
0 -4 -2 158010. 3446.42 4
0 -4 3 82422.1 3293.68 3
0 -4 -3 85191.9 2480.74 4
0 -4 -3 85976.8 2702.33 2
0 -4 -4 2628.52 491.385 2
0 -4 -4 2353.46 473.460 4
0 -4 4 2436.50 771.699 3
0 -4 5 6947.88 1158.40 3
0 -4 6 66597.0 3506.34 3
0 -4 7 105305. 4564.75 3
0 -4 -7 108308. 3206.58 5
0 -4 8 109319. 4836.59 3
0 -4 -8 113130. 3611.37 5
0 -4 8 110024. 2971.70 8
0 -4 -9 39588.3 2000.16 9
0 -4 9 41606.2 3087.62 3
0 -4 9 38554.9 1821.59 8
0 -4 -9 39280.8 2302.87 5
0 -4 -10 47953.7 2684.30 5
0 -4 -10 48679.4 2235.16 9
0 -4 -11 4716.23 722.866 9
0 -4 -11 5696.52 1121.52 5
0 -4 -12 1777.02 467.615 9
0 -4 -12 2437.91 868.296 5
0 -4 -13 1673.55 696.878 5
0 -4 -14 12690.5 1114.07 5
0 -4 -15 20578.1 1072.54 5
0 -3 0-127.453 419.290 3
0 -3 1 7122.19 852.886 3
0 -3 -1 8032.54 805.040 2
0 -3 2 57672.8 2266.13 3
0 -3 -2 57125.7 1905.43 2
0 -3 -2 60376.6 1796.10 4
0 -3 -3 56365.0 1755.13 4
0 -3 -3 53030.2 1844.42 2
0 -3 3 53490.8 2343.66 3
0 -3 -4 32743.2 1402.22 4
0 -3 -4 33648.1 1493.05 2
0 -3 4 32118.9 1962.96 3
0 -3 5 19626.7 1686.75 3
0 -3 -5 21619.4 1235.90 2
0 -3 -5 21403.4 1208.18 4
0 -3 -6 3759.05 557.945 4
0 -3 6 3397.34 807.875 3
0 -3 7 4664.68 1034.01 3
0 -3 -8 7816.00 928.032 5
0 -3 8 7281.63 1291.30 3
0 -3 9 10202.8 1565.11 3
0 -3 -9 9657.67 871.678 9
0 -3 -9 10115.6 1154.89 5
0 -3 -10 7268.81 798.990 9
0 -3 10 8475.85 1445.65 3
0 -3 -10 8456.74 1130.43 5
0 -3 -11 12171.7 1432.39 5
0 -3 -12 4370.04 1020.65 5
0 -3 -13 11379.4 1350.37 5
0 -3 -14 692.290 492.653 5
0 -3 -15 6282.54 733.452 5
0 -2 0 828311. 6372.83 3
0 -2 -1 185844. 2731.47 2
0 -2 1 185242. 3068.38 3
0 -2 -2 979266. 6282.61 2
0 -2 -2 999999. 5893.73 4
0 -2 2 982842. 7660.21 3
0 -2 -3 222953. 3017.95 4
0 -2 3 215733. 4014.86 3
0 -2 -3 222893. 3148.73 2
0 -2 -4 105932. 2339.51 2
0 -2 -4 104973. 2300.44 4
0 -2 4 101681. 3072.10 3
0 -2 5 81563.6 3043.80 3
0 -2 -5 82801.9 2284.11 4
0 -2 -5 83760.2 2282.54 2
0 -2 6 35435.9 2235.78 3
0 -2 -6 35555.4 1662.90 4
0 -2 -6 36025.0 1633.60 2
0 -2 7 269660. 6643.10 3
0 -2 8 146561. 5296.13 3
0 -2 -9 135920. 3808.43 5
0 -2 9 133876. 5308.27 3
0 -2 -9 140186. 3798.98 1
0 -2 10 73569.5 4152.07 3
0 -2 -10 77710.5 3120.06 5
0 -2 -11 26316.9 1993.43 5
0 -2 -12 14035.7 1511.56 5
0 -2 -13 30682.9 2192.56 5
0 -2 -14 25771.7 1826.13 5
0 -2 -15 34006.1 1714.59 5
0 -2 -16 28236.8 1130.45 5
0 -1 0 36.4517 150.506 3
0 -1 -1 56114.9 1029.87 2
0 -1 1 57031.9 1218.44 3
0 -1 -1 55047.5 954.925 4
0 -1 -2 20731.5 710.771 4
0 -1 -2 21505.6 746.334 2
0 -1 2 19799.4 910.992 3
0 -1 3 74037.8 2043.01 3
0 -1 -3 79922.7 1681.57 2
0 -1 -3 76443.3 1648.14 4
0 -1 -4 45105.1 1499.19 2
0 -1 4 41037.7 1798.31 3
0 -1 -4 43916.2 1480.38 4
0 -1 -5 19203.2 1154.86 4
0 -1 5 19031.1 1430.37 3
0 -1 -5 20046.7 1143.35 2
0 -1 6 59328.8 2741.91 3
0 -1 7 7934.33 1200.60 3
0 -1 8 16361.6 1742.18 3
0 -1 -9 5868.58 812.386 5
0 -1 9 6885.54 1291.64 3
0 -1 -10 9936.89 1129.51 1
0 -1 10 6827.89 1378.46 3
0 -1 -10 7530.91 992.227 5
0 -1 -11 1109.29 676.399 5
0 -1 -11 743.169 492.420 1
0 -1 -12 784.817 571.026 5
0 -1 -13 10878.7 1376.24 5
0 -1 -14 6765.53 1005.73 5
0 -1 -15 230.438 481.803 5
0 -1 -16 327.257 279.160 5
0 0 -1 11146.7 369.554 4
0 0 -1 11403.1 381.050 2
0 0 -2 402612. 3139.76 4
0 0 -2 397988. 3180.24 2
0 0 6 41752.1 2287.59 3
0 0 7 268108. 6334.26 3
0 0 8 98278.2 4187.58 3
0 0 9 206150. 6467.84 3
0 0 -9 215201. 4437.97 5
0 0 10 50992.9 3364.00 3
0 0 -10 53318.7 2343.58 1
0 0 -10 55387.4 2550.88 5
0 0 11 3293.36 1053.85 3
0 0 -11 1560.49 643.929 5
0 0 -11 1748.76 622.278 1
0 0 -12 960.487 514.364 1
0 0 -12 530.466 601.051 5
0 0 -13 35659.7 2359.81 5
0 0 -14 1899.55 717.648 5
0 0 -15 38670.8 1952.01 5
0 0 -16 41344.0 1504.00 5
0 1 8 19503.6 1901.27 3
0 1 -9 5753.66 779.766 5
0 1 9 3878.56 972.873 3
0 1 -10 7099.08 980.460 5
0 1 -10 8976.21 1008.80 1
0 1 -11 1214.24 565.239 1
0 1 -11 1484.88 593.900 5
0 1 -12 286.598 598.920 5
0 1 -12 36.8677 442.222 1
0 1 -13 9282.35 1252.89 5
0 1 -13 12209.4 1191.75 1
0 1 -14 6424.36 1020.25 5
0 1 -15-12.9191 384.614 5
0 1 -16 514.586 300.768 5
0 2 -9 126523. 3180.87 1
0 2 10 84146.3 4428.05 3
0 2 -10 75902.3 2746.18 1
0 2 -10 78349.7 3148.55 5
0 2 -11 23717.2 1637.10 1
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0 2 -12 12950.8 1258.94 1
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0 2 -13 32721.5 1804.69 1
0 2 -13 32289.1 2194.97 5
0 2 -14 20733.5 1626.83 5
0 2 -15 36437.9 1774.73 5
0 2 -16 31767.9 1195.55 5
0 3 -9 8783.64 891.957 1
0 3 -10 9566.72 995.952 1
0 3 -11 11005.2 1358.93 5
0 3 -11 12668.8 1271.89 1
0 3 -12 3621.96 890.936 5
0 3 -12 5347.02 802.293 1
0 3 -13 8730.08 1200.54 5
0 3 -14 305.926 414.703 5
0 3 -15 7575.45 777.710 5
0 4 -8 119519. 3048.94 1
0 4 -9 39966.3 1884.41 1
0 4 -10 46777.1 2138.59 1
0 4 -11 4508.37 956.111 5
0 4 -12 1549.87 672.011 5
0 4 -13 744.614 497.752 5
0 4 -14 11272.3 1054.36 5
0 4 -15 16806.3 960.430 5
0 5 -11 21732.7 1817.11 5
0 5 -12 11111.7 1268.35 5
0 5 -13 7707.16 947.555 5
0 5 -14 1289.18 407.331 5
0 6 4 9915.57 923.872 12
0 6 -4 8024.24 975.070 10
0 6 -5 14775.2 1367.72 10
0 6 5 17695.5 1207.54 12
0 6 6 13941.5 1094.23 12
0 6 -6 11313.6 1223.41 10
0 6 7 23704.6 1420.77 12
0 6 -11 8493.86 1127.54 5
0 6 -12 2117.63 590.841 5
0 6 -13 3963.76 601.665 5
0 7 0 897.531 498.709 12
0 7 0-9.27571 401.737 10
0 7 -1 15381.0 1424.41 10
0 7 1 16786.1 1355.46 12
0 7 -1 15986.3 1345.98 12
0 7 1 14503.4 1293.02 10
0 7 2 1311.67 522.464 12
0 7 2 1550.31 527.149 10
0 7 -2 1912.92 538.125 10
0 7 -3 38716.6 2333.32 10
0 7 3 41931.4 2129.86 12
0 7 4 11743.0 1183.43 12
0 7 -4 9840.62 1267.38 10
0 7 -5 13665.5 1456.98 10
0 7 5 14116.3 1257.07 12
0 7 6 8353.79 1005.86 12
0 7 7 1802.12 507.166 12
0 7 -11 5727.31 826.812 5
0 7 -12 6265.21 713.045 5
0 8 0 71875.2 3079.83 12
0 8 0 73286.8 3263.87 10
0 8 1 2931.93 745.510 12
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-9 3 -3 2358.01 679.911 11
-9 3 -4 2509.31 731.650 11
-9 3 -5 65.5501 427.045 11
-9 3 -6 2483.92 521.383 11
-9 4 9 11111.3 708.158 10
-9 4 8 21854.0 1278.57 10
-9 4 7 24689.4 1553.81 10
-9 4 6 7668.83 1006.82 10
-9 4 5 2846.12 704.746 10
-9 4 4 25375.1 1826.24 10
-9 4 3 3855.95 833.146 10
-9 4 2 58465.1 2729.90 10
-9 4 1 14843.4 1129.97 11
-9 4 1 16820.0 1481.06 10
-9 4 0 2636.59 607.786 11
-9 4 0 3913.27 743.133 10
-9 4 -1 25886.4 1607.56 11
-9 4 -1 26706.4 1567.95 10
-9 4 -2 14798.5 1272.77 11
-9 4 -2 13749.0 1000.66 10
-9 4 -3 11417.8 1100.33 11
-9 4 -4 4674.20 737.909 11
-9 5 8 566.354 259.999 10
-9 5 7 4218.26 647.690 10
-9 5 6 80.6106 358.830 10
-9 5 5 8194.41 998.094 10
-9 5 4 3305.59 716.390 10
-9 5 3 1084.92 567.569 10
-9 5 2 4306.26 809.757 10
-9 5 1 5109.63 823.281 10
-9 5 0 23627.5 1209.06 11
-9 5 0 20872.7 1440.05 10
-9 5 -1 4416.86 624.457 11
-9 5 -1 5605.20 724.965 10
-9 5 -2 8986.71 748.570 10
-9 6 7 4279.39 458.435 10
-9 6 6 4506.60 608.843 10
-9 6 5 7725.99 814.900 10
-9 6 4 10911.6 1023.05 10
-9 6 3 6051.06 822.440 10
-9 6 2 14000.3 1182.93 10
-9 6 1 12448.6 1075.86 10
-9 6 0 24082.9 1375.68 10
-9 6 -1 634.871 313.966 10
-9 7 5 5188.70 501.134 10
-9 7 4 747.677 307.163 10
-9 7 3 461.688 299.666 10
-9 7 2 1020.42 385.249 10
-9 7 1 3054.54 496.596 10
-9 7 0 1801.14 347.884 10
-10 -6 3 3940.35 424.408 11
-10 -6 2 6259.13 525.594 11
-10 -5 6 7131.98 579.084 11
-10 -5 5 2250.01 419.831 11
-10 -5 4 4418.06 580.659 11
-10 -5 3 2163.60 453.496 11
-10 -5 2 4821.28 624.765 11
-10 -5 1 808.205 321.843 11
-10 -5 0 3872.73 512.437 11
-10 -5 -1 9679.78 676.934 11
-10 -4 8 19443.4 909.814 7
-10 -4 7 4326.61 479.830 7
-10 -4 7 3250.93 389.507 11
-10 -4 6 13173.0 788.609 7
-10 -4 6 12985.3 904.878 11
-10 -4 5 8988.79 837.974 11
-10 -4 4 20407.2 1311.07 11
-10 -4 3 6169.04 784.166 11
-10 -4 2 12625.6 1091.30 11
-10 -4 1 2128.20 499.658 11
-10 -4 0 4780.51 672.318 11
-10 -4 -1 34667.4 1556.48 11
-10 -4 -2 5995.80 602.240 11
-10 -4 -3 6508.27 505.103 11
-10 -3 9 2325.16 410.183 7
-10 -3 8 5221.21 627.075 7
-10 -3 7 7818.12 769.214 7
-10 -3 7 7336.50 592.361 11
-10 -3 6 10753.2 905.218 7
-10 -3 6 10274.8 860.861 11
-10 -3 5 15686.2 1066.20 7
-10 -3 5 17055.7 1174.74 11
-10 -3 4 18206.7 1333.60 11
-10 -3 3 6599.93 899.724 11
-10 -3 2 12183.9 1185.70 11
-10 -3 1 197.833 379.386 11
-10 -3 0 4044.25 707.024 11
-10 -3 -1 8704.77 947.693 11
-10 -3 -2 955.353 432.743 11
-10 -3 -3 8745.67 762.613 11
-10 -3 -4 10059.6 640.648 11
-10 -2 10 3316.82 478.698 7
-10 -2 9-62.2926 269.404 7
-10 -2 8 12303.1 1032.17 7
-10 -2 7 7228.32 843.974 7
-10 -2 6 15190.2 1206.26 7
-10 -2 6 18156.1 1107.17 11
-10 -2 5 13627.1 1096.43 7
-10 -2 5 15395.4 1142.67 11
-10 -2 4 22457.2 1355.07 7
-10 -2 4 24494.3 1541.95 11
-10 -2 3 1714.85 533.647 11
-10 -2 2 1765.13 571.876 11
-10 -2 1 6974.85 972.936 11
-10 -2 0 3783.30 750.330 11
-10 -2 -1 8269.84 993.554 11
-10 -2 -2 9770.60 1008.96 11
-10 -2 -3 12961.9 1051.79 11
-10 -2 -4 14923.5 966.979 11
-10 -1 10 1630.93 326.911 10
-10 -1 9 4523.63 672.838 7
-10 -1 8 3343.79 651.487 7
-10 -1 7 15018.8 1264.60 7
-10 -1 6 11573.1 1143.32 7
-10 -1 5 25248.8 1615.54 7
-10 -1 5 23098.3 1362.68 11
-10 -1 4 14549.9 1177.21 11
-10 -1 3 18315.2 1396.77 11
-10 -1 2 3441.91 739.137 11
-10 -1 1 2153.61 708.540 11
-10 -1 0 968.204 517.534 11
-10 -1 -1 1500.91 557.785 11
-10 -1 -2 12087.8 1170.45 11
-10 -1 -3 8382.54 920.771 11
-10 -1 -4 3885.35 600.241 11
-10 -1 -5 11383.2 782.416 11
-10 0 10 439.593 219.223 10
-10 0 9 868.669 344.735 10
-10 0 4 12162.1 1048.60 11
-10 0 3 12874.7 1148.74 11
-10 0 2 6881.21 908.077 11
-10 0 2 7690.17 982.494 10
-10 0 1 3623.36 755.595 11
-10 0 1 2236.30 552.195 10
-10 0 0 8334.15 1071.43 11
-10 0 0 6997.37 756.669 10
-10 0 -1 561.521 555.835 11
-10 0 -2 41735.2 2109.30 11
-10 0 -3 19394.0 1393.47 11
-10 0 -4 5590.24 729.251 11
-10 0 -5 8786.83 747.982 11
-10 1 9 2454.65 472.395 10
-10 1 8 2373.13 517.123 10
-10 1 7 14617.5 1267.20 10
-10 1 6 12068.7 1219.57 10
-10 1 5 23304.1 1719.54 10
-10 1 4 13986.8 1357.17 10
-10 1 3 18007.9 1257.62 11
-10 1 3 16981.2 1442.32 10
-10 1 2 3781.78 679.657 11
-10 1 2 3245.00 743.569 10
-10 1 1 2545.23 630.862 11
-10 1 1 2212.58 570.422 10
-10 1 0 18446.6 1717.57 11
-10 1 0 50.2747 363.730 10
-10 1 -1 2551.85 735.817 11
-10 1 -2 12175.6 1178.88 11
-10 1 -3 8755.17 987.403 11
-10 1 -4 4921.83 704.664 11
-10 1 -5 13081.8 888.833 11
-10 2 9-164.349 268.058 10
-10 2 8 14683.8 1062.38 10
-10 2 7 7365.66 863.235 10
-10 2 6 18597.8 1429.71 10
-10 2 5 12358.0 1216.55 10
-10 2 4 22522.2 1654.92 10
-10 2 3 3738.63 843.657 10
-10 2 2 2350.38 518.060 11
-10 2 2 2316.24 630.268 10
-10 2 1 6160.33 837.154 11
-10 2 1 7522.52 891.640 10
-10 2 0 3310.72 697.222 11
-10 2 0 3549.43 562.027 10
-10 2 -1 8575.46 1002.27 11
-10 2 -2 8897.15 968.057 11
-10 2 -3 13849.1 1147.14 11
-10 2 -4 15108.2 1076.36 11
-10 2 -5 5875.42 602.560 11
-10 3 8 4163.96 547.514 10
-10 3 7 8011.21 812.923 10
-10 3 6 10001.7 997.955 10
-10 3 5 19899.3 1471.60 10
-10 3 4 19347.3 1477.41 10
-10 3 3 7209.79 960.364 10
-10 3 2 10648.5 1085.94 10
-10 3 1 392.516 352.640 11
-10 3 1 1161.26 482.976 10
-10 3 0 2986.45 598.229 11
-10 3 0 3563.25 614.473 10
-10 3 -1 10065.2 943.070 11
-10 3 -2 1562.71 484.463 11
-10 3 -3 9680.63 865.870 11
-10 3 -4 12316.6 854.596 11
-10 4 8 19551.1 858.669 10
-10 4 7 3478.04 540.845 10
-10 4 6 16937.2 1148.50 10
-10 4 5 9267.12 948.055 10
-10 4 4 24237.8 1492.78 10
-10 4 3 6503.35 838.926 10
-10 4 2 14849.9 1181.78 10
-10 4 1 2853.13 552.932 10
-10 4 0 2332.14 443.530 11
-10 4 0 2414.21 459.250 10
-10 4 -1 45450.2 1705.42 11
-10 4 -2 4248.67 560.740 11
-10 5 6 9140.03 720.579 10
-10 5 5 5266.35 633.456 10
-10 5 4 6570.37 719.882 10
-10 5 3 2962.86 541.842 10
-10 5 2 5227.08 649.261 10
-10 5 1 270.682 287.979 10
-10 5 0 2851.17 416.967 10
-10 6 3 4554.05 512.591 10
-10 6 2 6331.89 549.079 10
-11 -4 3 1640.74 315.449 11
-11 -4 2 1008.58 290.057 11
-11 -3 4 340.876 246.091 11
-11 -3 3 10564.6 768.752 11
-11 -3 2 7932.35 699.800 11
-11 -3 1 13944.7 895.874 11
-11 -3 0 8433.17 680.840 11
-11 -3 -1 13522.2 762.150 11
-11 -2 5 3648.63 419.291 11
-11 -2 4 5021.82 563.811 11
-11 -2 3 2421.03 439.010 11
-11 -2 3 2709.74 452.094 10
-11 -2 2 3257.42 524.685 11
-11 -2 2 2640.96 379.123 10
-11 -2 1 3783.23 574.945 11
-11 -2 0 1430.21 396.771 11
-11 -2 -1 149.723 248.013 11
-11 -2 -2 5677.84 540.595 11
-11 -1 8 28406.4 1091.85 10
-11 -1 7 4217.84 528.447 10
-11 -1 6 22791.1 1221.01 10
-11 -1 5 2269.37 498.455 10
-11 -1 4 604.582 296.918 11
-11 -1 4 1722.13 455.187 10
-11 -1 3 14159.7 964.398 11
-11 -1 3 14530.6 988.446 10
-11 -1 2 11938.9 927.145 11
-11 -1 2 12071.0 820.881 10
-11 -1 1 27428.6 1395.01 11
-11 -1 0 9067.16 824.192 11
-11 -1 -1 13530.5 950.894 11
-11 -1 -2 3581.79 486.529 11
-11 0 8 2782.93 411.250 10
-11 0 7 7383.28 695.614 10
-11 0 6 1283.80 402.166 10
-11 0 5 280.730 322.638 10
-11 0 4 2863.73 535.650 10
-11 0 3-948.790 350.414 11
-11 0 3-422.717 375.712 10
-11 0 2 5686.34 669.872 11
-11 0 2 5196.87 621.946 10
-11 0 1 161.284 343.143 11
-11 0 1 8.16462 231.350 10
-11 0 0 11450.5 931.074 11
-11 0 -1 465.339 342.173 11
-11 0 -2 473.155 284.885 11
-11 0 -3 3151.25 430.292 11
-11 1 7 4831.55 569.235 10
-11 1 6 22441.7 1223.49 10
-11 1 5 2620.37 566.974 10
-11 1 4 1529.48 446.785 10
-11 1 3 12140.9 727.726 11
-11 1 3 15071.8 1039.53 10
-11 1 2 9688.56 764.783 11
-11 1 2 11731.4 879.227 10
-11 1 1 28779.5 1342.73 11
-11 1 1 27906.7 1114.79 10
-11 1 0 11224.9 870.783 11
-11 1 -1 11308.3 840.056 11
-11 1 -2 5463.22 593.867 11
-11 1 -3 104.576 220.425 11
-11 2 7 10083.6 720.295 10
-11 2 6 31.3097 263.421 10
-11 2 5 4654.33 586.886 10
-11 2 4 4354.72 589.712 10
-11 2 3 3187.57 525.476 10
-11 2 2 2817.40 471.870 10
-11 2 1 2458.96 415.717 11
-11 2 1 3240.86 421.809 10
-11 2 0 1385.58 343.602 11
-11 2 -1 404.865 327.088 11
-11 2 -2 5205.49 525.157 11
-11 3 6 15415.8 866.916 10
-11 3 5 3754.83 499.167 10
-11 3 4 890.953 364.564 10
-11 3 3 10356.0 785.382 10
-11 3 2 8529.67 674.066 10
0 0 0 0.00 0.00 0
TITL mona22CuLT in P2(1)
REM P2(1) (#4 in standard setting)
CELL 1.54184 9.522002 9.321406 13.345271 90.0000 99.6446 90.0000
ZERR 2.00 0.000191 0.000200 0.000255 0.0000 0.0019 0.0000
LATT -1
SYMM -x, y+1/2,-z
SFAC C H N O Br
UNIT 60.00 56.00 2.00 14.00 4.00
TREF
HKLF 4
END
;
_shelx_hkl_checksum 74190
_shelx_res_file
;
mona22cult.res created by SHELXL-2014/7
TITL mona22CuLT in P21 #4
REM reset to P21 #4
CELL 1.54184 9.522002 9.321406 13.345271 90 99.6446 90
ZERR 2 0.000191 0.0002 0.000255 0 0.0019 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H Br N O
UNIT 44 54 4 2 14
DFIX 0.84 O22 H22
L.S. 10
PLAN 20
TEMP -173
HTAB N11 O21
HTAB O20 O10
HTAB O22 O21
HTAB
CONF
BOND
fmap 2
acta
REM
REM
REM
WGHT 0.021900 0.182500
FVAR 6.01005
O1 5 0.672683 0.353838 0.605735 11.00000 0.01972 0.01518 =
0.01768 0.00097 0.00416 0.00319
C1 1 0.633607 0.501195 0.627046 11.00000 0.01546 0.01360 =
0.01724 -0.00016 0.00081 0.00149
O2 5 0.689501 0.336322 0.498638 11.00000 0.01890 0.01950 =
0.01771 -0.00175 0.00620 -0.00046
C2 1 0.584963 0.583335 0.529081 11.00000 0.01230 0.01958 =
0.01654 0.00137 0.00280 -0.00002
AFIX 13
H2 2 0.574959 0.686285 0.547750 11.00000 -1.20000
AFIX 0
O3 5 0.683603 0.577728 0.460165 11.00000 0.01626 0.02131 =
0.01730 0.00119 0.00556 0.00000
C3 1 0.772592 0.453259 0.473144 11.00000 0.01887 0.01901 =
0.02496 0.00048 0.00982 0.00095
C4 1 0.904864 0.478309 0.554170 11.00000 0.01246 0.02497 =
0.03068 -0.00029 0.00447 0.00035
AFIX 23
H4A 2 0.929599 0.387415 0.591329 11.00000 -1.20000
H4B 2 0.985731 0.504267 0.519807 11.00000 -1.20000
AFIX 0
C5 1 0.886547 0.594819 0.630380 11.00000 0.01246 0.02435 =
0.02854 -0.00004 -0.00072 -0.00197
AFIX 23
H5A 2 0.869485 0.686919 0.593400 11.00000 -1.20000
H5B 2 0.977125 0.604288 0.678622 11.00000 -1.20000
AFIX 0
C6 1 0.727323 0.712065 0.742115 11.00000 0.02266 0.02130 =
0.01708 0.00102 -0.00271 0.00060
AFIX 13
H6 2 0.700611 0.784482 0.686928 11.00000 -1.20000
AFIX 0
C7 1 0.600189 0.693469 0.797385 11.00000 0.02485 0.02378 =
0.01747 -0.00350 0.00097 0.00375
AFIX 23
H7A 2 0.573351 0.788242 0.821830 11.00000 -1.20000
H7B 2 0.628551 0.631261 0.857495 11.00000 -1.20000
AFIX 0
C8 1 0.470695 0.627434 0.729597 11.00000 0.02344 0.02230 =
0.01804 -0.00090 0.00534 0.00438
AFIX 23
H8A 2 0.393094 0.613499 0.769603 11.00000 -1.20000
H8B 2 0.435953 0.693665 0.672852 11.00000 -1.20000
AFIX 0
C9 1 0.385794 0.404637 0.621391 11.00000 0.01562 0.02023 =
0.01701 0.00220 0.00551 0.00122
AFIX 13
H9 2 0.422826 0.306507 0.610374 11.00000 -1.20000
AFIX 0
O10 5 0.223218 0.453192 0.466504 11.00000 0.01196 0.02592 =
0.01947 0.00184 0.00060 -0.00102
C10 1 0.345244 0.469124 0.516381 11.00000 0.01293 0.01658 =
0.01748 -0.00084 0.00352 0.00380
N11 4 0.447200 0.536042 0.475843 11.00000 0.01420 0.02281 =
0.01703 0.00147 0.00211 -0.00125
C11 1 0.764487 0.571196 0.692477 11.00000 0.01399 0.02069 =
0.02083 0.00060 -0.00196 0.00137
AFIX 13
H11A 2 0.800483 0.502706 0.748600 11.00000 -1.20000
AFIX 0
H11 2 0.423270 0.566750 0.414958 11.00000 0.07799
C12 1 0.509339 0.483793 0.687115 11.00000 0.01545 0.01875 =
0.01442 0.00284 0.00367 0.00206
AFIX 13
H12 2 0.544294 0.420549 0.746601 11.00000 -1.20000
AFIX 0
C13 1 0.808203 0.415505 0.369298 11.00000 0.02170 0.03006 =
0.02869 -0.00398 0.01298 -0.00098
AFIX 137
H13A 2 0.870565 0.331211 0.375453 11.00000 -1.50000
H13B 2 0.856818 0.496695 0.343374 11.00000 -1.50000
H13C 2 0.720152 0.394302 0.322207 11.00000 -1.50000
AFIX 0
C14 1 0.855126 0.770035 0.814873 11.00000 0.03125 0.02862 =
0.02326 -0.00027 -0.00357 -0.00246
AFIX 137
H14A 2 0.891429 0.695716 0.864443 11.00000 -1.50000
H14B 2 0.826147 0.854072 0.850544 11.00000 -1.50000
H14C 2 0.930035 0.797616 0.776447 11.00000 -1.50000
AFIX 0
C15 1 0.256941 0.381541 0.673391 11.00000 0.01809 0.03625 =
0.01601 0.00097 0.00427 -0.00042
AFIX 137
H15A 2 0.213857 0.474448 0.684455 11.00000 -1.50000
H15B 2 0.287036 0.333882 0.738926 11.00000 -1.50000
H15C 2 0.186999 0.321427 0.630258 11.00000 -1.50000
AFIX 0
BR3 3 0.331079 0.934947 -0.063103 11.00000 0.04273 0.06309 =
0.02723 0.01103 0.01546 -0.00448
BR5 3 -0.206300 0.964572 0.060563 11.00000 0.03427 0.04717 =
0.02266 0.01196 0.00495 0.01732
O20 5 0.122690 0.598832 0.309833 11.00000 0.01595 0.02519 =
0.02209 0.00343 0.00057 -0.00184
C20 1 0.212687 0.629986 0.249408 11.00000 0.01929 0.01928 =
0.01713 -0.00635 -0.00083 -0.00389
H20 2 0.156882 0.537929 0.357381 11.00000 0.04970
O21 5 0.336166 0.581443 0.261446 11.00000 0.01852 0.02518 =
0.02028 -0.00303 -0.00039 0.00249
C21 1 0.160528 0.728685 0.164709 11.00000 0.02098 0.02039 =
0.01583 -0.00336 0.00160 -0.00105
O22 5 0.387974 0.721970 0.107122 11.00000 0.02170 0.03638 =
0.02484 -0.00255 0.00580 -0.00037
C22 1 0.253923 0.772040 0.099364 11.00000 0.02001 0.02620 =
0.01733 -0.00723 -0.00015 -0.00658
H22 2 0.394665 0.661309 0.154034 11.00000 0.09262
C23 1 0.205670 0.873340 0.024089 11.00000 0.02794 0.03721 =
0.01470 -0.00360 0.00537 -0.00529
C24 1 0.071439 0.930520 0.012727 11.00000 0.03370 0.02612 =
0.01536 0.00193 0.00166 -0.00186
AFIX 43
H24 2 0.041352 1.000001 -0.038454 11.00000 -1.20000
AFIX 0
C25 1 -0.020649 0.884888 0.077764 11.00000 0.02620 0.02508 =
0.01698 0.00062 -0.00056 0.00051
C26 1 0.021984 0.785559 0.153161 11.00000 0.02191 0.02475 =
0.01423 -0.00093 -0.00013 -0.00040
AFIX 43
H26 2 -0.041572 0.755788 0.196909 11.00000 -1.20000
AFIX 0
HKLF 4
REM mona22CuLT in P21 #4
REM R1 = 0.0297 for 3811 Fo > 4sig(Fo) and 0.0330 for all 4060 data
REM 304 parameters refined using 2 restraints
END
WGHT 0.0219 0.1825
REM Instructions for potential hydrogen bonds
EQIV $1 x+1, y, z
HTAB C4 O10_$1
EQIV $2 -x+1, y-1/2, -z+1
HTAB C9 O3_$2
HTAB N11 O21
HTAB O20 O10
HTAB O22 O21
REM Highest difference peak 0.266, deepest hole -0.443, 1-sigma level 0.055
Q1 1 0.4594 0.9423 0.0163 11.00000 0.05 0.27
Q2 1 0.3378 1.1291 -0.0613 11.00000 0.05 0.24
Q3 1 -0.2127 0.7702 0.0764 11.00000 0.05 0.22
Q4 1 0.2622 0.9565 -0.0541 11.00000 0.05 0.22
Q5 1 0.6190 0.5504 0.5796 11.00000 0.05 0.21
Q6 1 -0.2311 1.1493 0.0333 11.00000 0.05 0.21
Q7 1 0.6953 0.5526 0.6594 11.00000 0.05 0.20
Q8 1 0.4011 0.5060 0.0897 11.00000 0.05 0.20
Q9 1 0.3665 0.4453 0.5765 11.00000 0.05 0.19
Q10 1 0.1820 0.8088 0.1587 11.00000 0.05 0.19
Q11 1 0.5718 0.4833 0.6519 11.00000 0.05 0.19
Q12 1 0.3030 0.7464 -0.0813 11.00000 0.05 0.19
Q13 1 -0.0708 0.9696 0.1407 11.00000 0.05 0.19
Q14 1 -0.1347 1.0072 -0.0183 11.00000 0.05 0.19
Q15 1 -0.1387 0.8749 -0.0070 11.00000 0.05 0.19
Q16 1 0.4520 0.4451 0.6473 11.00000 0.05 0.18
Q17 1 -0.3265 0.9631 -0.0218 11.00000 0.05 0.18
Q18 1 0.3420 0.3989 0.6429 11.00000 0.05 0.18
Q19 1 0.0048 0.8833 0.0275 11.00000 0.05 0.18
Q20 1 0.2155 0.3056 0.4679 11.00000 0.05 0.18
;
_shelx_res_checksum 65172
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.6727(3) 0.3538(3) 0.6057(2) 0.0174(6) Uani d 1 . .
C C1 0.6336(4) 0.5012(4) 0.6270(3) 0.0157(8) Uani d 1 . .
O O2 0.6895(3) 0.3363(3) 0.4986(2) 0.0183(6) Uani d 1 . .
C C2 0.5850(4) 0.5833(5) 0.5291(3) 0.0161(8) Uani d 1 . .
H H2 0.5750 0.6863 0.5477 0.019 Uiso calc 1 . .
O O3 0.6836(3) 0.5777(3) 0.4602(2) 0.0180(6) Uani d 1 . .
C C3 0.7726(4) 0.4533(5) 0.4731(3) 0.0202(8) Uani d 1 . .
C C4 0.9049(4) 0.4783(5) 0.5542(3) 0.0226(9) Uani d 1 . .
H H4A 0.9296 0.3874 0.5913 0.027 Uiso calc 1 . .
H H4B 0.9857 0.5043 0.5198 0.027 Uiso calc 1 . .
C C5 0.8865(4) 0.5948(5) 0.6304(4) 0.0223(9) Uani d 1 . .
H H5A 0.8695 0.6869 0.5934 0.027 Uiso calc 1 . .
H H5B 0.9771 0.6043 0.6786 0.027 Uiso calc 1 . .
C C6 0.7273(5) 0.7121(5) 0.7421(3) 0.0210(9) Uani d 1 . .
H H6 0.7006 0.7845 0.6869 0.025 Uiso calc 1 . .
C C7 0.6002(5) 0.6935(5) 0.7974(4) 0.0223(9) Uani d 1 . .
H H7A 0.5734 0.7882 0.8218 0.027 Uiso calc 1 . .
H H7B 0.6286 0.6313 0.8575 0.027 Uiso calc 1 . .
C C8 0.4707(5) 0.6274(5) 0.7296(3) 0.0210(9) Uani d 1 . .
H H8A 0.3931 0.6135 0.7696 0.025 Uiso calc 1 . .
H H8B 0.4360 0.6937 0.6729 0.025 Uiso calc 1 . .
C C9 0.3858(4) 0.4046(5) 0.6214(3) 0.0173(8) Uani d 1 . .
H H9 0.4228 0.3065 0.6104 0.021 Uiso calc 1 . .
O O10 0.2232(3) 0.4532(4) 0.4665(2) 0.0193(6) Uani d 1 . .
C C10 0.3452(4) 0.4691(5) 0.5164(3) 0.0156(7) Uani d 1 . .
N N11 0.4472(4) 0.5360(4) 0.4758(3) 0.0181(7) Uani d 1 . .
C C11 0.7645(4) 0.5712(5) 0.6925(3) 0.0191(8) Uani d 1 . .
H H11A 0.8005 0.5027 0.7486 0.023 Uiso calc 1 . .
H H11 0.423(8) 0.567(10) 0.415(7) 0.08(3) Uiso d 1 . .
C C12 0.5093(4) 0.4838(4) 0.6871(3) 0.0161(8) Uani d 1 . .
H H12 0.5443 0.4205 0.7466 0.019 Uiso calc 1 . .
C C13 0.8082(5) 0.4155(6) 0.3693(3) 0.0258(10) Uani d 1 . .
H H13A 0.8706 0.3312 0.3755 0.039 Uiso calc 1 . .
H H13B 0.8568 0.4967 0.3434 0.039 Uiso calc 1 . .
H H13C 0.7202 0.3943 0.3222 0.039 Uiso calc 1 . .
C C14 0.8551(5) 0.7700(6) 0.8149(4) 0.0286(11) Uani d 1 . .
H H14A 0.8914 0.6957 0.8644 0.043 Uiso calc 1 . .
H H14B 0.8261 0.8541 0.8505 0.043 Uiso calc 1 . .
H H14C 0.9300 0.7976 0.7764 0.043 Uiso calc 1 . .
C C15 0.2569(4) 0.3815(5) 0.6734(3) 0.0233(9) Uani d 1 . .
H H15A 0.2139 0.4744 0.6845 0.035 Uiso calc 1 . .
H H15B 0.2870 0.3339 0.7389 0.035 Uiso calc 1 . .
H H15C 0.1870 0.3214 0.6303 0.035 Uiso calc 1 . .
Br Br3 0.33108(6) 0.93495(7) -0.06310(4) 0.04324(17) Uani d 1 . .
Br Br5 -0.20630(5) 0.96457(6) 0.06056(4) 0.03468(14) Uani d 1 . .
O O20 0.1227(3) 0.5988(4) 0.3098(2) 0.0214(6) Uani d 1 . .
C C20 0.2127(5) 0.6300(5) 0.2494(3) 0.0190(9) Uani d 1 . .
H H20 0.157(7) 0.538(8) 0.357(6) 0.05(2) Uiso d 1 . .
O O21 0.3362(3) 0.5814(4) 0.2614(2) 0.0217(6) Uani d 1 . .
C C21 0.1605(5) 0.7287(5) 0.1647(3) 0.0192(8) Uani d 1 . .
O O22 0.3880(3) 0.7220(4) 0.1071(3) 0.0274(7) Uani d 1 . .
C C22 0.2539(5) 0.7720(5) 0.0994(3) 0.0216(9) Uani d 1 . .
H H22 0.395(10) 0.661(8) 0.154(5) 0.09(3) Uiso d 1 . .
C C23 0.2057(5) 0.8733(6) 0.0241(3) 0.0264(10) Uani d 1 . .
C C24 0.0714(5) 0.9305(5) 0.0127(3) 0.0253(10) Uani d 1 . .
H H24 0.0414 1.0000 -0.0385 0.030 Uiso calc 1 . .
C C25 -0.0206(5) 0.8849(5) 0.0778(3) 0.0232(9) Uani d 1 . .
C C26 0.0220(5) 0.7856(5) 0.1532(3) 0.0207(9) Uani d 1 . .
H H26 -0.0416 0.7558 0.1969 0.025 Uiso calc 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0197(15) 0.0152(15) 0.0177(14) 0.0032(11) 0.0042(12) 0.0010(12)
C1 0.0155(18) 0.014(2) 0.017(2) 0.0015(14) 0.0008(15) -0.0002(15)
O2 0.0189(15) 0.0195(16) 0.0177(15) -0.0005(12) 0.0062(12) -0.0017(12)
C2 0.0123(18) 0.020(2) 0.017(2) 0.0000(15) 0.0028(15) 0.0014(16)
O3 0.0163(14) 0.0213(15) 0.0173(15) 0.0000(12) 0.0056(12) 0.0012(12)
C3 0.0189(17) 0.019(2) 0.025(2) 0.0010(19) 0.0098(15) 0.0005(19)
C4 0.0125(17) 0.025(2) 0.031(2) 0.0003(18) 0.0045(15) 0.000(2)
C5 0.0125(19) 0.024(2) 0.029(2) -0.0020(17) -0.0007(17) 0.0000(18)
C6 0.023(2) 0.021(2) 0.017(2) 0.0006(18) -0.0027(17) 0.0010(17)
C7 0.025(2) 0.024(2) 0.017(2) 0.0038(18) 0.0010(17) -0.0035(17)
C8 0.023(2) 0.022(2) 0.018(2) 0.0044(17) 0.0053(17) -0.0009(17)
C9 0.0156(18) 0.020(2) 0.017(2) 0.0012(15) 0.0055(15) 0.0022(16)
O10 0.0120(12) 0.0259(16) 0.0195(13) -0.0010(13) 0.0006(10) 0.0018(15)
C10 0.0129(16) 0.0166(19) 0.0175(17) 0.0038(17) 0.0035(14) -0.0008(17)
N11 0.0142(17) 0.0228(19) 0.0170(18) -0.0013(14) 0.0021(14) 0.0015(15)
C11 0.0140(19) 0.021(2) 0.021(2) 0.0014(16) -0.0020(16) 0.0006(17)
C12 0.0155(17) 0.019(2) 0.0144(17) 0.0021(16) 0.0037(14) 0.0028(16)
C13 0.022(2) 0.030(3) 0.029(2) -0.0010(19) 0.0130(17) -0.004(2)
C14 0.031(3) 0.029(3) 0.023(2) -0.002(2) -0.004(2) -0.0003(19)
C15 0.018(2) 0.036(3) 0.016(2) -0.0004(18) 0.0043(16) 0.0010(18)
Br3 0.0427(3) 0.0631(4) 0.0272(3) -0.0045(3) 0.0155(2) 0.0110(3)
Br5 0.0343(2) 0.0472(3) 0.0227(2) 0.0173(2) 0.00495(17) 0.0120(2)
O20 0.0159(14) 0.0252(17) 0.0221(16) -0.0018(12) 0.0006(12) 0.0034(13)
C20 0.019(2) 0.019(2) 0.017(2) -0.0039(16) -0.0008(16) -0.0063(16)
O21 0.0185(15) 0.0252(16) 0.0203(15) 0.0025(13) -0.0004(12) -0.0030(13)
C21 0.021(2) 0.020(2) 0.016(2) -0.0011(17) 0.0016(16) -0.0034(17)
O22 0.0217(15) 0.036(2) 0.0248(18) -0.0004(14) 0.0058(13) -0.0025(15)
C22 0.020(2) 0.026(2) 0.017(2) -0.0066(18) -0.0001(17) -0.0072(17)
C23 0.028(2) 0.037(3) 0.015(2) -0.005(2) 0.0054(17) -0.0036(18)
C24 0.034(2) 0.026(3) 0.015(2) -0.002(2) 0.0017(16) 0.002(2)
C25 0.026(2) 0.025(2) 0.017(2) 0.0005(18) -0.0006(17) 0.0006(17)
C26 0.022(2) 0.025(2) 0.014(2) -0.0004(18) -0.0001(16) -0.0009(17)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 O2 . . 111.4(3) ?
O1 C1 C2 . . 110.9(3) ?
O1 C1 C11 . . 107.4(3) ?
O1 C1 C12 . . 104.1(3) ?
C2 C1 C11 . . 112.0(3) ?
C2 C1 C12 . . 110.5(3) ?
C11 C1 C12 . . 111.5(3) ?
C3 O2 O1 . . 107.6(3) ?
O3 C2 C1 . . 113.5(3) ?
O3 C2 N11 . . 108.2(3) ?
N11 C2 C1 . . 112.9(3) ?
C2 O3 C3 . . 113.2(3) ?
O2 C3 O3 . . 108.0(3) ?
O2 C3 C4 . . 111.9(4) ?
O2 C3 C13 . . 105.0(4) ?
O3 C3 C4 . . 111.2(4) ?
O3 C3 C13 . . 107.2(4) ?
C13 C3 C4 . . 113.3(3) ?
C5 C4 C3 . . 114.1(4) ?
C4 C5 C11 . . 115.9(4) ?
C7 C6 C11 . . 111.6(4) ?
C14 C6 C7 . . 110.2(4) ?
C14 C6 C11 . . 111.1(4) ?
C6 C7 C8 . . 112.6(4) ?
C12 C8 C7 . . 110.6(3) ?
C10 C9 C12 . . 113.0(3) ?
C10 C9 C15 . . 112.2(3) ?
C15 C9 C12 . . 114.0(3) ?
O10 C10 C9 . . 121.1(4) ?
O10 C10 N11 . . 120.8(4) ?
N11 C10 C9 . . 117.9(3) ?
C10 N11 C2 . . 126.8(4) ?
C1 C11 C5 . . 111.4(4) ?
C6 C11 C1 . . 112.5(3) ?
C6 C11 C5 . . 110.8(4) ?
C8 C12 C1 . . 110.8(3) ?
C8 C12 C9 . . 115.2(3) ?
C9 C12 C1 . . 109.5(3) ?
O20 C20 C21 . . 116.1(4) ?
O21 C20 O20 . . 122.9(4) ?
O21 C20 C21 . . 120.9(4) ?
C22 C21 C20 . . 119.2(4) ?
C22 C21 C26 . . 120.2(4) ?
C26 C21 C20 . . 120.5(4) ?
O22 C22 C21 . . 122.9(4) ?
O22 C22 C23 . . 118.8(4) ?
C23 C22 C21 . . 118.3(4) ?
C22 C23 Br3 . . 118.8(4) ?
C24 C23 Br3 . . 119.2(4) ?
C24 C23 C22 . . 122.0(4) ?
C23 C24 C25 . . 118.9(4) ?
C24 C25 Br5 . . 118.3(3) ?
C26 C25 Br5 . . 120.4(4) ?
C26 C25 C24 . . 121.2(4) ?
C25 C26 C21 . . 119.3(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.463(5) ?
O1 O2 . 1.474(4) ?
C1 C2 . 1.519(6) ?
C1 C11 . 1.542(6) ?
C1 C12 . 1.545(5) ?
O2 C3 . 1.421(5) ?
C2 O3 . 1.421(5) ?
C2 N11 . 1.452(5) ?
O3 C3 . 1.430(6) ?
C3 C4 . 1.534(5) ?
C3 C13 . 1.522(6) ?
C4 C5 . 1.518(6) ?
C5 C11 . 1.552(6) ?
C6 C7 . 1.529(6) ?
C6 C11 . 1.538(6) ?
C6 C14 . 1.523(6) ?
C7 C8 . 1.531(6) ?
C8 C12 . 1.523(6) ?
C9 C10 . 1.514(5) ?
C9 C12 . 1.534(5) ?
C9 C15 . 1.523(5) ?
O10 C10 . 1.247(4) ?
C10 N11 . 1.342(5) ?
Br3 C23 . 1.891(5) ?
Br5 C25 . 1.896(5) ?
O20 C20 . 1.304(6) ?
C20 O21 . 1.245(5) ?
C20 C21 . 1.477(6) ?
C21 C22 . 1.405(6) ?
C21 C26 . 1.406(6) ?
O22 C22 . 1.347(6) ?
C22 C23 . 1.399(7) ?
C23 C24 . 1.370(7) ?
C24 C25 . 1.399(6) ?
C25 C26 . 1.378(6) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N11 H11 O21 . 0.86(9) 2.08(9) 2.910(5) 163(9)
O20 H20 O10 . 0.87(8) 1.68(8) 2.542(4) 167(7)
O22 H22 O21 . 0.84(3) 1.79(5) 2.558(5) 152(9)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 O3 . . . . -52.6(4) ?
O1 C1 C2 N11 . . . . 71.0(4) ?
O1 C1 C11 C5 . . . . 69.1(4) ?
O1 C1 C11 C6 . . . . -165.8(3) ?
O1 C1 C12 C8 . . . . 171.2(3) ?
O1 C1 C12 C9 . . . . -60.6(4) ?
O1 O2 C3 O3 . . . . -75.7(4) ?
O1 O2 C3 C4 . . . . 47.0(4) ?
O1 O2 C3 C13 . . . . 170.2(3) ?
C1 O1 O2 C3 . . . . 46.2(4) ?
C1 C2 O3 C3 . . . . 25.7(5) ?
C1 C2 N11 C10 . . . . 23.3(6) ?
O2 O1 C1 C2 . . . . 14.5(4) ?
O2 O1 C1 C11 . . . . -108.2(3) ?
O2 O1 C1 C12 . . . . 133.3(3) ?
O2 C3 C4 C5 . . . . -97.1(5) ?
C2 C1 C11 C5 . . . . -53.0(5) ?
C2 C1 C11 C6 . . . . 72.2(5) ?
C2 C1 C12 C8 . . . . -69.6(4) ?
C2 C1 C12 C9 . . . . 58.5(4) ?
C2 O3 C3 O2 . . . . 36.5(4) ?
C2 O3 C3 C4 . . . . -86.6(4) ?
C2 O3 C3 C13 . . . . 149.1(3) ?
O3 C2 N11 C10 . . . . 149.9(4) ?
O3 C3 C4 C5 . . . . 23.7(5) ?
C3 C4 C5 C11 . . . . 59.0(5) ?
C4 C5 C11 C1 . . . . -37.0(5) ?
C4 C5 C11 C6 . . . . -163.1(4) ?
C6 C7 C8 C12 . . . . 56.6(5) ?
C7 C6 C11 C1 . . . . 50.5(5) ?
C7 C6 C11 C5 . . . . 175.9(3) ?
C7 C8 C12 C1 . . . . -57.4(5) ?
C7 C8 C12 C9 . . . . 177.6(3) ?
C9 C10 N11 C2 . . . . -15.3(6) ?
O10 C10 N11 C2 . . . . 169.0(4) ?
C10 C9 C12 C1 . . . . -50.3(4) ?
C10 C9 C12 C8 . . . . 75.3(4) ?
N11 C2 O3 C3 . . . . -100.4(4) ?
C11 C1 C2 O3 . . . . 67.4(5) ?
C11 C1 C2 N11 . . . . -169.0(3) ?
C11 C1 C12 C8 . . . . 55.7(4) ?
C11 C1 C12 C9 . . . . -176.2(3) ?
C11 C6 C7 C8 . . . . -52.8(5) ?
C12 C1 C2 O3 . . . . -167.6(3) ?
C12 C1 C2 N11 . . . . -43.9(5) ?
C12 C1 C11 C5 . . . . -177.4(3) ?
C12 C1 C11 C6 . . . . -52.3(5) ?
C12 C9 C10 O10 . . . . -155.5(4) ?
C12 C9 C10 N11 . . . . 28.7(5) ?
C13 C3 C4 C5 . . . . 144.5(4) ?
C14 C6 C7 C8 . . . . -176.8(4) ?
C14 C6 C11 C1 . . . . 174.0(4) ?
C14 C6 C11 C5 . . . . -60.6(5) ?
C15 C9 C10 O10 . . . . -25.0(6) ?
C15 C9 C10 N11 . . . . 159.3(4) ?
C15 C9 C12 C1 . . . . -180.0(3) ?
C15 C9 C12 C8 . . . . -54.3(5) ?
Br3 C23 C24 C25 . . . . -179.7(4) ?
Br5 C25 C26 C21 . . . . -179.6(3) ?
O20 C20 C21 C22 . . . . 177.1(4) ?
O20 C20 C21 C26 . . . . 1.0(6) ?
C20 C21 C22 O22 . . . . 3.4(6) ?
C20 C21 C22 C23 . . . . -175.5(4) ?
C20 C21 C26 C25 . . . . 175.6(4) ?
O21 C20 C21 C22 . . . . -2.4(6) ?
O21 C20 C21 C26 . . . . -178.5(4) ?
C21 C22 C23 Br3 . . . . 179.0(3) ?
C21 C22 C23 C24 . . . . 0.0(7) ?
O22 C22 C23 Br3 . . . . 0.0(6) ?
O22 C22 C23 C24 . . . . -179.0(4) ?
C22 C21 C26 C25 . . . . -0.5(7) ?
C22 C23 C24 C25 . . . . -0.7(7) ?
C23 C24 C25 Br5 . . . . -179.7(4) ?
C23 C24 C25 C26 . . . . 0.8(7) ?
C24 C25 C26 C21 . . . . -0.2(7) ?
C26 C21 C22 O22 . . . . 179.6(4) ?
C26 C21 C22 C23 . . . . 0.6(6) ?
_cod_database_fobs_code 2022374