#------------------------------------------------------------------------------ #$Date: 2021-12-07 05:53:38 +0200 (Tue, 07 Dec 2021) $ #$Revision: 271222 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158380.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7158380 loop_ _publ_author_name 'Fuller, Rebecca O.' 'Taylor, Madeleine R.' 'Duggin, Margot' 'Bissember, Alex C.' 'Canty, Allan J.' 'Judd, Martyna M.' 'Cox, Nicholas' 'Moggach, Stephen A.' 'Turner, Gemma F.' _publ_section_title ; Enhanced synthesis of oxo-verdazyl radicals bearing sterically-and electronically-diverse C3-substituents. ; _journal_issue 46 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 10120 _journal_page_last 10138 _journal_paper_doi 10.1039/d1ob01946e _journal_volume 19 _journal_year 2021 _chemical_formula_moiety 'C19 H22 N4 O3' _chemical_formula_sum 'C19 H22 N4 O3' _chemical_formula_weight 354.40 _chemical_name_common 1,5-bis(2-methoxybenzyl)-2,4-dimethyl-carbohydrazide _chemical_name_systematic 1,5-bis(2-methoxybenzyl)-2,4-dimethyl-carbohydrazide _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2020-09-04 _audit_creation_method ; Olex2 1.3 (compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145) ; _audit_update_record ; 2021-09-30 deposited with the CCDC. 2021-11-01 downloaded from the CCDC. ; _cell_angle_alpha 108.084(4) _cell_angle_beta 100.023(3) _cell_angle_gamma 101.754(3) _cell_formula_units_Z 2 _cell_length_a 8.5045(3) _cell_length_b 9.7970(4) _cell_length_c 11.9453(5) _cell_measurement_reflns_used 10860 _cell_measurement_temperature 100.0(3) _cell_measurement_theta_max 73.0060 _cell_measurement_theta_min 4.9460 _cell_volume 895.65(7) _computing_cell_refinement 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.0(3) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.955 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w 24.00 118.00 0.50 0.24 -- 46.20 77.00 60.00 188 2 \w 90.00 176.00 0.50 1.00 -- 102.41 37.00 116.00 172 3 \w 141.00 167.00 0.50 1.00 -- 102.41 45.00 60.00 52 4 \w 80.00 105.00 0.50 1.00 -- 102.41 -94.00 0.00 50 5 \w 76.00 111.00 0.50 1.00 -- 102.41-125.00 30.00 70 6 \w 45.00 103.00 0.50 1.00 -- 102.41 -94.00 150.00 116 7 \w 40.00 88.00 0.50 1.00 -- 102.41 -77.00 90.00 96 8 \w 39.00 116.00 0.50 1.00 -- 102.41-130.00 -17.13 154 9 \w 58.00 99.00 0.50 1.00 -- 102.41 -94.00-120.00 82 10 \w 30.00 82.00 0.50 1.00 -- 102.41 -77.00 -30.00 104 11 \w 30.00 99.00 0.50 1.00 -- 102.41 -94.00 60.00 138 12 \w 34.00 72.00 0.50 1.00 -- 102.41 -94.00 0.00 76 13 \w 34.00 119.00 0.50 0.24 -- 46.20 37.00 116.00 170 14 \w 38.00 135.00 0.50 0.24 -- 62.00 79.00 -8.53 194 15 \w 41.00 135.00 0.50 0.24 -- 62.00 72.00-119.49 188 16 \w 42.00 129.00 0.50 0.24 -- 66.00 79.00-104.43 174 17 \w 34.00 119.00 0.50 0.24 -- 46.20 38.00-180.00 170 18 \w 36.00 131.00 0.50 0.24 -- 58.00 75.00 -59.23 190 19 \w 39.00 135.00 0.50 0.24 -- 62.00 78.00 84.23 192 20 \w 43.00 69.00 0.50 0.24 -- 66.00 77.00 -51.75 52 21 \w 43.00 69.00 0.50 0.24 -- 66.00 78.00 -27.99 52 22 \w 34.00 131.00 0.50 0.24 -- 58.00 79.00 45.05 194 23 \w 39.00 135.00 0.50 0.24 -- 62.00 77.00 142.37 192 24 \w 44.00 70.00 0.50 0.24 -- 66.00 77.00 116.12 52 25 \w 26.00 122.00 0.50 0.24 -- 50.00 80.00 125.72 192 26 \w 35.00 131.00 0.50 0.24 -- 58.00 77.00 159.06 192 27 \w 24.00 118.00 0.50 0.24 -- 46.20 77.00 0.00 188 28 \w 24.00 118.00 0.50 0.24 -- 46.20 77.00-120.00 188 29 \w 24.00 118.00 0.50 0.24 -- 46.20 77.00 -90.00 188 30 \w 24.00 118.00 0.50 0.24 -- 46.20 77.00-180.00 188 31 \w 34.00 131.00 0.50 0.24 -- 58.00 79.00-164.01 194 32 \w 7.00 34.00 0.50 0.24 -- 38.00 94.00 -33.48 54 33 \w -21.00 34.00 0.50 0.24 -- 10.00 94.00 -26.81 110 34 \w -17.00 14.00 0.50 0.24 -- 18.00 102.00 -90.74 62 35 \w 10.00 43.00 0.50 0.24 -- 38.00 88.00 106.31 66 36 \w -42.00 27.00 0.50 0.24 -- -46.20 37.00 116.00 138 37 \w -27.00 42.00 0.50 0.24 -- 46.20 -37.00 -39.00 138 38 \w -25.00 69.00 0.50 0.24 -- 46.20 -77.00-180.00 188 39 \w 13.00 94.00 0.50 0.24 -- 46.20-125.00-180.00 162 40 \w -65.00 -36.00 0.50 1.00 -- -102.41 61.00 30.00 58 41 \w -76.00 -50.00 0.50 1.00 -- -102.41 125.00 60.00 52 42 \w -69.00 -42.00 0.50 1.00 -- -102.41 125.00 150.00 54 43 \w -109.00 -81.00 0.50 1.00 -- -102.41 125.00 60.00 56 44 \w -111.00 -85.00 0.50 1.00 -- -102.41 125.00 150.00 52 45 \w -119.00 -34.00 0.50 0.24 -- -46.20 -37.00 -39.00 170 46 \w -80.00 -54.00 0.50 0.24 -- -74.00 -69.00 67.49 52 47 \w -77.00 -51.00 0.50 0.24 -- -74.00 -78.00 14.23 52 48 \w -82.00 -56.00 0.50 0.24 -- -74.00 -66.00 34.64 52 49 \w -85.00 -59.00 0.50 0.24 -- -74.00 -62.00 13.00 52 50 \w -86.00 -61.00 0.50 1.00 -- -82.00 -73.00 34.68 50 51 \w -92.00 -65.00 0.50 1.00 -- -82.00 -64.00 42.09 54 52 \w -90.00 -64.00 0.50 1.00 -- -82.00 -64.00 86.87 52 53 \w -85.00 -59.00 0.50 0.24 -- -74.00 -60.00 141.93 52 54 \w -82.00 -56.00 0.50 1.00 -- -78.00 -75.00 154.76 52 55 \w -87.00 -61.00 0.50 1.00 -- -82.00 -72.00 134.80 52 56 \w -90.00 -65.00 0.50 1.00 -- -86.00 -72.00 163.20 50 57 \w -94.00 -65.00 0.50 1.00 -- -82.00 -61.00 173.61 58 58 \w -93.00 -67.00 0.50 1.00 -- -90.00 -79.00 101.69 52 59 \w -108.00 -80.00 0.50 1.00 -- -90.00 -64.00 20.06 56 60 \w -95.00 -69.00 0.50 1.00 -- -90.00 -73.00 2.34 52 61 \w -93.00 -68.00 0.50 1.00 -- -90.00 -74.00 -39.25 50 62 \w -98.00 -64.00 0.50 1.00 -- -78.00 -58.00 -63.84 68 63 \w -87.00 -62.00 0.50 1.00 -- -78.00 -59.00-111.11 50 64 \w -92.00 -67.00 0.50 1.00 -- -82.00 -61.00-138.41 50 65 \w -93.00 -62.00 0.50 1.00 -- -82.00 -71.00-104.07 62 66 \w -94.00 -68.00 0.50 1.00 -- -86.00 -65.00-151.40 52 67 \w -106.00 -75.00 0.50 1.00 -- -94.00 -67.00 -64.48 62 68 \w -104.00 -68.00 0.50 1.00 -- -90.00 -74.00 -8.16 72 69 \w -103.00 -77.00 0.50 1.00 -- -94.00 -64.00 30.81 52 70 \w -113.00 -83.00 0.50 1.00 -- -102.41 -69.00 28.56 60 71 \w -114.00 -80.00 0.50 1.00 -- -102.41 -77.00 -60.00 68 72 \w -109.00 -80.00 0.50 1.00 -- -102.41 -77.00 -90.00 58 73 \w -115.00 -72.00 0.50 1.00 -- -94.00 -76.00-115.70 86 74 \w -126.00 -31.00 0.50 0.24 -- -54.00 -78.00-126.47 190 75 \w -123.00 -83.00 0.50 1.00 -- -102.41 -76.00 -11.82 80 76 \w -139.00 -79.00 0.50 1.00 -- -94.00 -58.00-108.60 120 77 \w -134.00 -72.00 0.50 1.00 -- -94.00 -76.00-160.20 124 78 \w -151.00-125.00 0.50 1.00 -- -90.00 -74.00 -8.16 52 79 \w -130.00 -79.00 0.50 1.00 -- -94.00 -61.00 3.82 102 80 \w -129.00 -82.00 0.50 1.00 -- -102.41 -70.00 91.45 94 81 \w -101.00 -69.00 0.50 1.00 -- -90.00 -72.00 143.10 64 82 \w -113.00 -73.00 0.50 1.00 -- -94.00 -72.00 169.78 80 83 \w -113.00 -71.00 0.50 1.00 -- -94.00 -76.00 138.58 84 84 \w -139.00 -47.00 0.50 0.24 -- -66.00 -67.00 164.08 184 85 \w -158.00-100.00 0.50 1.00 -- -86.00 -72.00 163.20 116 86 \w -160.00-123.00 0.50 1.00 -- -90.00 -79.00 101.69 74 87 \w -162.00-112.00 0.50 1.00 -- -90.00 -64.00 20.06 100 88 \w -161.00-116.00 0.50 1.00 -- -90.00 -74.00 -39.25 90 89 \w -167.00-115.00 0.50 1.00 -- -94.00 -67.00 -64.48 104 90 \w -167.00-121.00 0.50 1.00 -- -94.00 -76.00-115.70 92 91 \w -156.00 -77.00 0.50 1.00 -- -94.00 -63.00-155.74 158 92 \w -175.00 -90.00 0.50 1.00 -- -102.41 -37.00 -39.00 170 93 \w -173.00-130.00 0.50 1.00 -- -102.41 -76.00 -11.82 86 94 \w -174.00-115.00 0.50 1.00 -- -102.41 -77.00 -90.00 118 95 \w -174.00-117.00 0.50 1.00 -- -102.41 -69.00 28.56 114 96 \w -163.00-118.00 0.50 1.00 -- -94.00 -76.00 138.58 90 97 \w -175.00-134.00 0.50 1.00 -- -102.41 -70.00 91.45 82 98 \w -167.00 -83.00 0.50 1.00 -- -102.41 -69.00 69.43 168 99 \w -173.00-138.00 0.50 1.00 -- -102.41 -77.00 -60.00 70 100 \w -105.00 -37.00 0.50 1.00 -- -102.41 77.00 -90.00 136 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.1807026000 _diffrn_orient_matrix_UB_12 -0.0038875000 _diffrn_orient_matrix_UB_13 -0.0513994000 _diffrn_orient_matrix_UB_21 -0.0512697000 _diffrn_orient_matrix_UB_22 -0.1716119000 _diffrn_orient_matrix_UB_23 -0.0406752000 _diffrn_orient_matrix_UB_31 -0.0365037000 _diffrn_orient_matrix_UB_32 0.0119366000 _diffrn_orient_matrix_UB_33 0.1240538000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.1264 _diffrn_reflns_av_unetI/netI 0.0481 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.955 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 31657 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.955 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 75.621 _diffrn_reflns_theta_min 4.026 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.743 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.49823 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_density_diffrn 1.314 _exptl_crystal_description block _exptl_crystal_F_000 376 _exptl_crystal_size_max 0.163 _exptl_crystal_size_mid 0.093 _exptl_crystal_size_min 0.062 _refine_diff_density_max 0.460 _refine_diff_density_min -0.483 _refine_diff_density_rms 0.094 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 239 _refine_ls_number_reflns 3558 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.070 _refine_ls_R_factor_all 0.0754 _refine_ls_R_factor_gt 0.0668 _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^)+(0.1462P)^2^+0.0814P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1822 _refine_ls_wR_factor_ref 0.2014 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2984 _reflns_number_total 3558 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01946e2.cif _cod_data_source_block 1b _cod_depositor_comments 'Adding full bibliography for 7158376--7158384.cif.' _cod_database_code 7158380 _chemical_oxdiff_formula 'C19 H22 N4 O3' _chemical_oxdiff_usercomment 'UTas Becky' _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. ; _reflns_odcompleteness_completeness 99.87 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.49 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: C009(H009), C00B(H00B), C00D(H00D), C00E(H00E), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00N(H00N), C00P(H00R) 2.b Idealised Me refined as rotating group: C00H(H00A,H00C,H00F), C00M(H00G,H00H,H00M), C00O(H00O,H00P,H00Q), C00Q(H00S, H00T,H00U) ; _shelx_res_file ; TITL bof5_a.res in P-1 bof5.res created by SHELXL-2018/3 at 13:25:19 on 04-Sep-2020 REM Old TITL BOF5 in P-1 REM SHELXT solution in P-1: R1 0.156, Rweak 0.004, Alpha 0.028 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C19 N5 O2 CELL 1.54184 8.5045 9.797 11.9453 108.084 100.023 101.754 ZERR 2 0.0003 0.0004 0.0005 0.004 0.003 0.003 LATT 1 SFAC C H N O UNIT 38 44 8 6 L.S. 4 0 0 PLAN 5 CONF BOND list 4 fmap 2 53 MORE -1 BOND $H ACTA REM REM REM WGHT 0.146200 0.081400 FVAR 0.79246 O001 4 0.172863 0.080223 0.152982 11.00000 0.02904 0.03037 = 0.04629 0.01483 0.01163 0.00799 O002 4 0.825381 0.616108 0.135027 11.00000 0.02063 0.04287 = 0.04718 0.02343 0.01447 0.01082 O003 4 -0.198424 0.611788 0.433127 11.00000 0.02868 0.05007 = 0.03922 0.01374 0.01330 0.01666 N004 3 0.137849 0.433175 0.291041 11.00000 0.02364 0.03205 = 0.03319 0.01289 0.00897 0.00806 N005 3 0.388075 0.429605 0.180098 11.00000 0.02255 0.03051 = 0.03232 0.01342 0.00841 0.00712 N006 3 0.368878 0.303295 0.209468 11.00000 0.02168 0.03108 = 0.03746 0.01626 0.01040 0.00859 N007 3 0.088682 0.292847 0.202283 11.00000 0.01956 0.03038 = 0.03831 0.01144 0.00873 0.00591 C008 1 0.207732 0.215950 0.185460 11.00000 0.02390 0.03234 = 0.03078 0.01341 0.00969 0.00760 C009 1 0.533796 0.495776 0.178490 11.00000 0.01861 0.03439 = 0.03369 0.01415 0.00730 0.00806 AFIX 43 H009 2 0.623180 0.458046 0.195901 11.00000 -1.20000 AFIX 0 C00A 1 0.557308 0.631046 0.148961 11.00000 0.01910 0.03208 = 0.03091 0.01111 0.00548 0.00452 C00B 1 0.730169 0.818344 0.096216 11.00000 0.02263 0.03320 = 0.03444 0.01230 0.00810 0.00370 AFIX 43 H00B 2 0.830150 0.858054 0.081505 11.00000 -1.20000 AFIX 0 C00C 1 0.708098 0.691444 0.126171 11.00000 0.02150 0.03405 = 0.02961 0.01125 0.00696 0.00713 C00D 1 0.025935 0.494349 0.324616 11.00000 0.02305 0.03664 = 0.03610 0.01549 0.00916 0.00907 AFIX 43 H00D 2 -0.086028 0.443666 0.291030 11.00000 -1.20000 AFIX 0 C00E 1 0.432380 0.703639 0.142152 11.00000 0.01995 0.03575 = 0.04123 0.01458 0.00761 0.00706 AFIX 43 H00E 2 0.332878 0.665935 0.158435 11.00000 -1.20000 AFIX 0 C00F 1 0.076710 0.644876 0.416423 11.00000 0.02815 0.03823 = 0.03289 0.01676 0.00775 0.01389 C00G 1 -0.040349 0.704999 0.471153 11.00000 0.03152 0.04394 = 0.03143 0.01630 0.00853 0.01588 C00H 1 0.505938 0.239417 0.232748 11.00000 0.02358 0.03679 = 0.04327 0.01761 0.00963 0.01169 AFIX 137 H00A 2 0.549289 0.214276 0.162273 11.00000 -1.50000 H00C 2 0.466968 0.150993 0.250093 11.00000 -1.50000 H00F 2 0.591923 0.310867 0.301226 11.00000 -1.50000 AFIX 0 C00I 1 0.602186 0.886373 0.088174 11.00000 0.02728 0.02896 = 0.03863 0.01369 0.00491 0.00368 AFIX 43 H00I 2 0.616714 0.970697 0.066673 11.00000 -1.20000 AFIX 0 C00J 1 0.453296 0.830132 0.111786 11.00000 0.02323 0.03330 = 0.04553 0.01294 0.00591 0.00818 AFIX 43 H00J 2 0.368764 0.876831 0.107258 11.00000 -1.20000 AFIX 0 C00K 1 0.240253 0.735218 0.449741 11.00000 0.02943 0.03989 = 0.04028 0.01640 0.00718 0.01233 AFIX 43 H00K 2 0.318499 0.698381 0.413185 11.00000 -1.20000 AFIX 0 C00L 1 0.007333 0.847821 0.557659 11.00000 0.04704 0.04714 = 0.03379 0.01590 0.01215 0.02422 AFIX 43 H00L 2 -0.069970 0.886163 0.594427 11.00000 -1.20000 AFIX 0 C00M 1 -0.085768 0.210529 0.148450 11.00000 0.02068 0.03597 = 0.04021 0.01358 0.00842 0.00478 AFIX 137 H00G 2 -0.134050 0.187499 0.209578 11.00000 -1.50000 H00H 2 -0.094619 0.119524 0.083828 11.00000 -1.50000 H00M 2 -0.143560 0.270334 0.116480 11.00000 -1.50000 AFIX 0 C00N 1 0.287436 0.877612 0.535631 11.00000 0.03749 0.04080 = 0.04142 0.01637 0.00372 0.00862 AFIX 43 H00N 2 0.396824 0.935634 0.557326 11.00000 -1.20000 AFIX 0 C00O 1 -0.324063 0.670518 0.479262 11.00000 0.03659 0.06637 = 0.03934 0.01971 0.01711 0.02718 AFIX 137 H00O 2 -0.429407 0.596430 0.443246 11.00000 -1.50000 H00P 2 -0.329401 0.757532 0.459489 11.00000 -1.50000 H00Q 2 -0.297929 0.697114 0.566098 11.00000 -1.50000 AFIX 0 C00P 1 0.171201 0.933885 0.589474 11.00000 0.05237 0.03802 = 0.03398 0.01050 0.00356 0.01428 AFIX 43 H00R 2 0.202948 1.029991 0.647372 11.00000 -1.20000 AFIX 0 C00Q 1 0.979640 0.673846 0.112650 11.00000 0.02384 0.06287 = 0.07143 0.03994 0.02351 0.01693 AFIX 137 H00S 2 0.960979 0.672801 0.030745 11.00000 -1.50000 H00T 2 1.052337 0.613177 0.123429 11.00000 -1.50000 H00U 2 1.029644 0.774502 0.168686 11.00000 -1.50000 AFIX 0 HKLF 4 REM bof5_a.res in P-1 REM wR2 = 0.2014, GooF = S = 1.070, Restrained GooF = 1.070 for all data REM R1 = 0.0668 for 2984 Fo > 4sig(Fo) and 0.0754 for all 3558 data REM 239 parameters refined using 0 restraints END WGHT 0.1462 0.0814 REM Highest difference peak 0.460, deepest hole -0.483, 1-sigma level 0.094 Q1 1 0.1625 0.0165 0.0655 11.00000 0.05 0.46 Q2 1 0.1748 0.1430 0.0999 11.00000 0.05 0.45 Q3 1 0.0517 0.5843 0.3432 11.00000 0.05 0.41 Q4 1 0.1838 0.1279 0.2388 11.00000 0.05 0.40 Q5 1 0.0545 0.5457 0.4058 11.00000 0.05 0.40 ; _shelx_res_checksum 2397 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 3.300 _oxdiff_exptl_absorpt_empirical_full_min 0.441 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O001 O 0.17286(14) 0.08022(13) 0.15298(12) 0.0347(4) Uani 1 1 d . . . . . O002 O 0.82538(14) 0.61611(14) 0.13503(12) 0.0340(4) Uani 1 1 d . . . . . O003 O -0.19842(15) 0.61179(15) 0.43313(13) 0.0384(4) Uani 1 1 d . . . . . N004 N 0.13785(17) 0.43317(16) 0.29104(13) 0.0290(4) Uani 1 1 d . . . . . N005 N 0.38808(16) 0.42961(16) 0.18010(13) 0.0278(4) Uani 1 1 d . . . . . N006 N 0.36888(17) 0.30330(16) 0.20947(14) 0.0285(4) Uani 1 1 d . . . . . N007 N 0.08868(17) 0.29285(16) 0.20228(14) 0.0296(4) Uani 1 1 d . . . . . C008 C 0.2077(2) 0.21595(19) 0.18546(16) 0.0281(4) Uani 1 1 d . . . . . C009 C 0.53380(19) 0.49578(19) 0.17849(16) 0.0282(4) Uani 1 1 d . . . . . H009 H 0.623180 0.458046 0.195901 0.034 Uiso 1 1 calc R U . . . C00A C 0.55731(19) 0.63105(19) 0.14896(16) 0.0279(4) Uani 1 1 d . . . . . C00B C 0.7302(2) 0.81834(19) 0.09622(17) 0.0306(4) Uani 1 1 d . . . . . H00B H 0.830150 0.858054 0.081505 0.037 Uiso 1 1 calc R U . . . C00C C 0.7081(2) 0.6914(2) 0.12617(16) 0.0284(4) Uani 1 1 d . . . . . C00D C 0.0259(2) 0.4943(2) 0.32462(17) 0.0310(4) Uani 1 1 d . . . . . H00D H -0.086028 0.443666 0.291030 0.037 Uiso 1 1 calc R U . . . C00E C 0.4324(2) 0.7036(2) 0.14215(17) 0.0322(4) Uani 1 1 d . . . . . H00E H 0.332878 0.665935 0.158435 0.039 Uiso 1 1 calc R U . . . C00F C 0.0767(2) 0.6449(2) 0.41642(17) 0.0314(4) Uani 1 1 d . . . . . C00G C -0.0403(2) 0.7050(2) 0.47115(17) 0.0340(4) Uani 1 1 d . . . . . C00H C 0.5059(2) 0.2394(2) 0.23275(18) 0.0331(4) Uani 1 1 d . . . . . H00A H 0.549289 0.214276 0.162273 0.050 Uiso 1 1 calc R U . . . H00C H 0.466968 0.150993 0.250093 0.050 Uiso 1 1 calc R U . . . H00F H 0.591923 0.310867 0.301226 0.050 Uiso 1 1 calc R U . . . C00I C 0.6022(2) 0.8864(2) 0.08817(17) 0.0323(4) Uani 1 1 d . . . . . H00I H 0.616714 0.970697 0.066673 0.039 Uiso 1 1 calc R U . . . C00J C 0.4533(2) 0.8301(2) 0.11179(18) 0.0346(5) Uani 1 1 d . . . . . H00J H 0.368764 0.876831 0.107258 0.042 Uiso 1 1 calc R U . . . C00K C 0.2403(2) 0.7352(2) 0.44974(18) 0.0358(4) Uani 1 1 d . . . . . H00K H 0.318499 0.698381 0.413185 0.043 Uiso 1 1 calc R U . . . C00L C 0.0073(3) 0.8478(2) 0.55766(18) 0.0403(5) Uani 1 1 d . . . . . H00L H -0.069970 0.886163 0.594427 0.048 Uiso 1 1 calc R U . . . C00M C -0.0858(2) 0.2105(2) 0.14845(18) 0.0327(4) Uani 1 1 d . . . . . H00G H -0.134050 0.187499 0.209578 0.049 Uiso 1 1 calc R U . . . H00H H -0.094619 0.119524 0.083828 0.049 Uiso 1 1 calc R U . . . H00M H -0.143560 0.270334 0.116480 0.049 Uiso 1 1 calc R U . . . C00N C 0.2874(2) 0.8776(2) 0.5356(2) 0.0407(5) Uani 1 1 d . . . . . H00N H 0.396824 0.935634 0.557326 0.049 Uiso 1 1 calc R U . . . C00O C -0.3241(3) 0.6705(3) 0.4793(2) 0.0442(5) Uani 1 1 d . . . . . H00O H -0.429407 0.596430 0.443246 0.066 Uiso 1 1 calc R U . . . H00P H -0.329401 0.757532 0.459489 0.066 Uiso 1 1 calc R U . . . H00Q H -0.297929 0.697114 0.566098 0.066 Uiso 1 1 calc R U . . . C00P C 0.1712(3) 0.9339(2) 0.58947(19) 0.0428(5) Uani 1 1 d . . . . . H00R H 0.202948 1.029991 0.647372 0.051 Uiso 1 1 calc R U . . . C00Q C 0.9796(2) 0.6738(3) 0.1127(2) 0.0465(6) Uani 1 1 d . . . . . H00S H 0.960979 0.672801 0.030745 0.070 Uiso 1 1 calc R U . . . H00T H 1.052337 0.613177 0.123429 0.070 Uiso 1 1 calc R U . . . H00U H 1.029644 0.774502 0.168686 0.070 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O001 0.0290(6) 0.0304(7) 0.0463(8) 0.0148(6) 0.0116(6) 0.0080(5) O002 0.0206(6) 0.0429(7) 0.0472(8) 0.0234(6) 0.0145(5) 0.0108(5) O003 0.0287(7) 0.0501(8) 0.0392(8) 0.0137(6) 0.0133(5) 0.0167(6) N004 0.0236(7) 0.0321(8) 0.0332(8) 0.0129(6) 0.0090(6) 0.0081(6) N005 0.0226(7) 0.0305(7) 0.0323(8) 0.0134(6) 0.0084(6) 0.0071(5) N006 0.0217(7) 0.0311(7) 0.0375(9) 0.0163(6) 0.0104(6) 0.0086(5) N007 0.0196(7) 0.0304(7) 0.0383(9) 0.0114(6) 0.0087(6) 0.0059(5) C008 0.0239(8) 0.0323(9) 0.0308(9) 0.0134(7) 0.0097(6) 0.0076(6) C009 0.0186(7) 0.0344(9) 0.0337(10) 0.0142(7) 0.0073(6) 0.0081(6) C00A 0.0191(8) 0.0321(9) 0.0309(9) 0.0111(7) 0.0055(6) 0.0045(6) C00B 0.0226(8) 0.0332(9) 0.0344(10) 0.0123(7) 0.0081(7) 0.0037(6) C00C 0.0215(8) 0.0341(9) 0.0296(9) 0.0112(7) 0.0070(6) 0.0071(6) C00D 0.0231(8) 0.0366(9) 0.0361(10) 0.0155(8) 0.0092(7) 0.0091(6) C00E 0.0199(8) 0.0357(10) 0.0412(11) 0.0146(8) 0.0076(7) 0.0071(7) C00F 0.0282(8) 0.0382(10) 0.0329(10) 0.0168(8) 0.0077(7) 0.0139(7) C00G 0.0315(9) 0.0439(10) 0.0314(10) 0.0163(8) 0.0085(7) 0.0159(8) C00H 0.0236(8) 0.0368(9) 0.0433(11) 0.0176(8) 0.0096(7) 0.0117(7) C00I 0.0273(8) 0.0290(9) 0.0386(10) 0.0137(7) 0.0049(7) 0.0037(7) C00J 0.0232(8) 0.0333(9) 0.0455(11) 0.0129(8) 0.0059(7) 0.0082(7) C00K 0.0294(9) 0.0399(10) 0.0403(11) 0.0164(8) 0.0072(7) 0.0123(7) C00L 0.0470(11) 0.0471(11) 0.0338(11) 0.0159(9) 0.0121(8) 0.0242(9) C00M 0.0207(8) 0.0360(10) 0.0402(11) 0.0136(8) 0.0084(7) 0.0048(7) C00N 0.0375(10) 0.0408(11) 0.0414(11) 0.0164(9) 0.0037(8) 0.0086(8) C00O 0.0366(10) 0.0664(14) 0.0393(11) 0.0197(10) 0.0171(8) 0.0272(10) C00P 0.0524(12) 0.0380(10) 0.0340(11) 0.0105(8) 0.0036(9) 0.0143(9) C00Q 0.0238(9) 0.0629(13) 0.0714(15) 0.0399(12) 0.0235(9) 0.0169(8) 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' 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_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -4 5 2 0.0315 4 -5 2 0.0267 -5 5 0 0.0272 -4 5 -2 0.0323 -2 -1 8 0.0684 -5 2 -2 0.0266 4 -2 4 0.0277 2 1 -8 0.0475 0 3 5 0.0312 -2 -5 0 0.0380 -4 5 1 0.0318 3 -6 3 0.0309 -5 4 -2 0.0266 4 -4 4 0.0240 -4 0 -3 0.0347 3 0 5 0.0274 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C00C O002 C00Q 117.19(14) . . ? C00G O003 C00O 117.46(16) . . ? C00D N004 N007 118.61(14) . . ? C009 N005 N006 118.15(14) . . ? N005 N006 C008 117.03(13) . . ? N005 N006 C00H 122.21(13) . . ? C008 N006 C00H 118.71(14) . . ? N004 N007 C008 117.58(13) . . ? N004 N007 C00M 122.10(14) . . ? C008 N007 C00M 118.57(14) . . ? O001 C008 N006 122.30(15) . . ? O001 C008 N007 121.90(15) . . ? N007 C008 N006 115.80(14) . . ? N005 C009 H009 120.5 . . ? N005 C009 C00A 119.05(15) . . ? C00A C009 H009 120.5 . . ? C00C C00A C009 120.15(15) . . ? C00E C00A C009 121.50(15) . . ? C00E C00A C00C 118.35(16) . . ? C00C C00B H00B 120.1 . . ? C00C C00B C00I 119.75(16) . . ? C00I C00B H00B 120.1 . . ? O002 C00C C00A 115.53(15) . . ? O002 C00C C00B 124.04(15) . . ? C00B C00C C00A 120.42(15) . . ? N004 C00D H00D 120.5 . . ? N004 C00D C00F 119.07(16) . . ? C00F C00D H00D 120.5 . . ? C00A C00E H00E 119.2 . . ? C00J C00E C00A 121.54(16) . . ? C00J C00E H00E 119.2 . . ? C00G C00F C00D 120.41(16) . . ? C00K C00F C00D 121.43(17) . . ? C00K C00F C00G 118.12(17) . . ? O003 C00G C00F 115.16(16) . . ? O003 C00G C00L 124.34(17) . . ? C00L C00G C00F 120.49(18) . . ? N006 C00H H00A 109.5 . . ? N006 C00H H00C 109.5 . . ? N006 C00H H00F 109.5 . . ? H00A C00H H00C 109.5 . . ? H00A C00H H00F 109.5 . . ? H00C C00H H00F 109.5 . . ? C00B C00I H00I 119.6 . . ? C00J C00I C00B 120.90(17) . . ? C00J C00I H00I 119.6 . . ? C00E C00J C00I 119.02(16) . . ? C00E C00J H00J 120.5 . . ? C00I C00J H00J 120.5 . . ? C00F C00K H00K 119.4 . . ? C00N C00K C00F 121.29(18) . . ? C00N C00K H00K 119.4 . . ? C00G C00L H00L 120.1 . . ? C00G C00L C00P 119.83(18) . . ? C00P C00L H00L 120.1 . . ? N007 C00M H00G 109.5 . . ? N007 C00M H00H 109.5 . . ? N007 C00M H00M 109.5 . . ? H00G C00M H00H 109.5 . . ? H00G C00M H00M 109.5 . . ? H00H C00M H00M 109.5 . . ? C00K C00N H00N 120.2 . . ? C00K C00N C00P 119.70(19) . . ? C00P C00N H00N 120.2 . . ? O003 C00O H00O 109.5 . . ? O003 C00O H00P 109.5 . . ? O003 C00O H00Q 109.5 . . ? H00O C00O H00P 109.5 . . ? H00O C00O H00Q 109.5 . . ? H00P C00O H00Q 109.5 . . ? C00L C00P H00R 119.7 . . ? C00N C00P C00L 120.54(19) . . ? C00N C00P H00R 119.7 . . ? O002 C00Q H00S 109.5 . . ? O002 C00Q H00T 109.5 . . ? O002 C00Q H00U 109.5 . . ? H00S C00Q H00T 109.5 . . ? H00S C00Q H00U 109.5 . . ? H00T C00Q H00U 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O001 C008 1.219(2) . ? O002 C00C 1.365(2) . ? O002 C00Q 1.423(2) . ? O003 C00G 1.370(2) . ? O003 C00O 1.427(2) . ? N004 N007 1.377(2) . ? N004 C00D 1.281(2) . ? N005 N006 1.374(2) . ? N005 C009 1.283(2) . ? N006 C008 1.388(2) . ? N006 C00H 1.456(2) . ? N007 C008 1.386(2) . ? N007 C00M 1.457(2) . ? C009 H009 0.9300 . ? C009 C00A 1.459(2) . ? C00A C00C 1.408(2) . ? C00A C00E 1.398(2) . ? C00B H00B 0.9300 . ? C00B C00C 1.383(3) . ? C00B C00I 1.392(2) . ? C00D H00D 0.9300 . ? C00D C00F 1.461(3) . ? C00E H00E 0.9300 . ? C00E C00J 1.382(3) . ? C00F C00G 1.411(3) . ? C00F C00K 1.401(3) . ? C00G C00L 1.384(3) . ? C00H H00A 0.9600 . ? C00H H00C 0.9600 . ? C00H H00F 0.9600 . ? C00I H00I 0.9300 . ? C00I C00J 1.387(3) . ? C00J H00J 0.9300 . ? C00K H00K 0.9300 . ? C00K C00N 1.378(3) . ? C00L H00L 0.9300 . ? C00L C00P 1.391(3) . ? C00M H00G 0.9600 . ? C00M H00H 0.9600 . ? C00M H00M 0.9600 . ? C00N H00N 0.9300 . ? C00N C00P 1.385(3) . ? C00O H00O 0.9600 . ? C00O H00P 0.9600 . ? C00O H00Q 0.9600 . ? C00P H00R 0.9300 . ? C00Q H00S 0.9600 . ? C00Q H00T 0.9600 . ? C00Q H00U 0.9600 . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O003 C00G C00L C00P -179.66(17) . . . . ? N004 N007 C008 O001 147.96(18) . . . . ? N004 N007 C008 N006 -31.2(2) . . . . ? N004 C00D C00F C00G -168.65(17) . . . . ? N004 C00D C00F C00K 13.5(3) . . . . ? N005 N006 C008 O001 145.15(18) . . . . ? N005 N006 C008 N007 -35.7(2) . . . . ? N005 C009 C00A C00C -169.16(16) . . . . ? N005 C009 C00A C00E 10.7(3) . . . . ? N006 N005 C009 C00A -179.28(15) . . . . ? N007 N004 C00D C00F -178.39(15) . . . . ? C009 N005 N006 C008 -166.46(16) . . . . ? C009 N005 N006 C00H -3.0(2) . . . . ? C009 C00A C00C O002 -0.6(2) . . . . ? C009 C00A C00C C00B 178.96(16) . . . . ? C009 C00A C00E C00J -178.68(17) . . . . ? C00A C00E C00J C00I -0.3(3) . . . . ? C00B C00I C00J C00E -0.8(3) . . . . ? C00C C00A C00E C00J 1.1(3) . . . . ? C00C C00B C00I C00J 1.1(3) . . . . ? C00D N004 N007 C008 -166.65(16) . . . . ? C00D N004 N007 C00M -1.9(2) . . . . ? C00D C00F C00G O003 1.0(3) . . . . ? C00D C00F C00G C00L -179.67(17) . . . . ? C00D C00F C00K C00N 179.45(18) . . . . ? C00E C00A C00C O002 179.57(16) . . . . ? C00E C00A C00C C00B -0.9(3) . . . . ? C00F C00G C00L C00P 1.1(3) . . . . ? C00F C00K C00N C00P -0.7(3) . . . . ? C00G C00F C00K C00N 1.5(3) . . . . ? C00G C00L C00P C00N -0.3(3) . . . . ? C00H N006 C008 O001 -18.9(3) . . . . ? C00H N006 C008 N007 160.24(16) . . . . ? C00I C00B C00C O002 179.30(17) . . . . ? C00I C00B C00C C00A -0.2(3) . . . . ? C00K C00F C00G O003 178.98(15) . . . . ? C00K C00F C00G C00L -1.7(3) . . . . ? C00K C00N C00P C00L 0.1(3) . . . . ? C00M N007 C008 O001 -17.3(3) . . . . ? C00M N007 C008 N006 163.50(16) . . . . ? C00O O003 C00G C00F -175.80(17) . . . . ? C00O O003 C00G C00L 4.9(3) . . . . ? C00Q O002 C00C C00A -179.97(17) . . . . ? C00Q O002 C00C C00B 0.5(3) . . . . ? loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -3.6766 4.8835 1.7909 0.5533 -0.7224 0.4147 3.9966 -5.0328 2.3073 -0.8212 0.5649 0.0803 -4.5206 4.6243 -0.1575 0.8070 -0.5554 0.2007 -4.1609 4.9665 -1.7752 0.8238 -0.5668 -0.0090 -2.1649 -1.1188 7.5313 0.0084 -0.0033 1.0000 -5.0759 1.7786 -1.7377 0.9996 0.0257 -0.0090 4.2850 -2.0217 3.7400 -0.9587 -0.0249 0.2834 2.1393 1.1987 -7.5465 -0.0034 -0.0084 -1.0000 -0.1461 3.3493 4.6072 -0.2234 -0.7547 0.6169 -1.5663 -5.2012 0.3693 0.2843 0.9579 0.0409 -3.5787 5.2528 0.9154 0.5792 -0.7552 0.3069 2.6544 -6.0037 2.7726 -0.5988 0.7814 0.1754 -4.8954 3.5247 -1.7068 0.9586 -0.2845 0.0090 3.9868 -3.7205 4.0110 -0.9121 0.2709 0.3076 -4.4271 0.0106 -2.5570 0.9314 0.3292 -0.1555 2.8703 -0.4909 5.3025 -0.7893 -0.2786 0.5472