#------------------------------------------------------------------------------ #$Date: 2018-01-11 04:50:34 +0200 (Thu, 11 Jan 2018) $ #$Revision: 205058 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229945.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_7229945 loop_ _publ_author_name 'Nisar, Madiha' 'Sung, Herman H-Y.' 'Puschmann, Horst' 'Lakerveld, Richard' 'Haynes, Richard' 'Williams, Ian Duncan' _publ_section_title ; 11-Azaartemisinin cocrystals with preserved lactam: acid heterosynthons ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/C7CE01875D _journal_year 2018 _chemical_absolute_configuration ad _chemical_formula_moiety '2(C15 H23 N O4), C7 H12 O4' _chemical_formula_sum 'C37 H58 N2 O12' _chemical_formula_weight 722.85 _chemical_name_common 11-Aza:Pim _chemical_name_systematic ; ? ; _space_group_crystal_system orthorhombic _space_group_IT_number 18 _space_group_name_Hall 'P 2 2ab' _space_group_name_H-M_alt 'P 21 21 2' _symmetry_space_group_name_Hall 'P 2 2ab' _symmetry_space_group_name_H-M 'P 21 21 2' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _audit_creation_date 2017-07-17 _audit_creation_method ; Olex2 1.2 (compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337) ; _audit_update_record ; 2017-08-15 deposited with the CCDC. 2018-01-10 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 17.5836(7) _cell_length_b 10.3594(4) _cell_length_c 9.9524(3) _cell_measurement_reflns_used 5938 _cell_measurement_temperature 99.99(10) _cell_measurement_theta_max 75.1850 _cell_measurement_theta_min 4.4360 _cell_volume 1812.88(11) _computing_cell_refinement 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 99.99(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.3577 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _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 78.00 112.00 1.00 8.00 -- 110.57 77.00 -90.00 34 2 \w 12.00 113.00 1.00 3.00 -- 40.45 57.00 30.00 101 3 \w 121.00 178.00 1.00 8.00 -- 110.57 77.00 -90.00 57 4 \w 152.00 177.00 1.00 8.00 -- 110.57 37.00 -66.21 25 5 \w 142.00 169.00 1.00 8.00 -- 110.57 61.00 -60.00 27 6 \w 121.00 177.00 1.00 8.00 -- 110.57 77.00 -30.00 56 7 \w 85.00 112.00 1.00 8.00 -- 110.57 45.00 -30.00 27 8 \w 84.00 109.00 1.00 8.00 -- 110.57 45.00 0.00 25 9 \w 81.00 106.00 1.00 8.00 -- 110.57 61.00 -30.00 25 10 \w 85.00 111.00 1.00 8.00 -- 110.57 30.00 -30.00 26 11 \w 85.00 124.00 1.00 8.00 -- 110.57 30.00 0.00 39 12 \w 84.00 145.00 1.00 8.00 -- 110.57 45.00 30.00 61 13 \w 78.00 103.00 1.00 8.00 -- 110.57 77.00 0.00 25 14 \w 80.00 106.00 1.00 8.00 -- 110.57 61.00 0.00 26 15 \w 80.00 105.00 1.00 8.00 -- 110.57 68.00 17.69 25 16 \w 77.00 104.00 1.00 8.00 -- 110.57 77.00 -30.00 27 17 \w 78.00 103.00 1.00 8.00 -- 110.57 77.00 -60.00 25 18 \w 81.00 106.00 1.00 8.00 -- 110.57 61.00 -90.00 25 19 \w 84.00 121.00 1.00 8.00 -- 110.57 37.00 -66.21 37 20 \w 80.00 106.00 1.00 8.00 -- 110.57 61.00-120.00 26 21 \w 83.00 109.00 1.00 8.00 -- 110.57 45.00 -90.00 26 22 \w 83.00 110.00 1.00 8.00 -- 110.57 45.00 -60.00 27 23 \w 80.00 106.00 1.00 8.00 -- 110.57 61.00 -60.00 26 24 \w 77.00 103.00 1.00 8.00 -- 110.57 77.00-120.00 26 25 \w 78.00 173.00 1.00 8.00 -- 110.57 77.00-150.00 95 26 \w 81.00 106.00 1.00 8.00 -- 110.57 30.00 30.00 25 27 \w 80.00 107.00 1.00 8.00 -- 110.57 61.00 30.00 27 28 \w 78.00 105.00 1.00 8.00 -- 110.57 77.00 30.00 27 29 \w 77.00 177.00 1.00 8.00 -- 110.57 77.00 60.00 100 30 \w 48.00 106.00 1.00 8.00 -- 110.57 -94.00 90.00 58 31 \w 26.00 104.00 1.00 8.00 -- 110.57 -94.00 0.00 78 32 \w 97.00 122.00 1.00 8.00 -- 110.57-125.00 -90.00 25 33 \w 56.00 98.00 1.00 3.00 -- 40.45-125.00-180.00 42 34 \w 36.00 80.00 1.00 8.00 -- 110.57-125.00 -90.00 44 35 \w 15.00 100.00 1.00 3.00 -- 40.45 37.00 -30.00 85 36 \w 27.00 54.00 1.00 3.00 -- 40.45 57.00-150.00 27 37 \w 8.00 36.00 1.00 3.00 -- 40.45 77.00 -60.00 28 38 \w 9.00 34.00 1.00 3.00 -- 40.45 77.00 -30.00 25 39 \w -45.00 -20.00 1.00 3.00 -- -40.45 -57.00 60.00 25 40 \w -100.00 -62.00 1.00 3.00 -- -40.45 -57.00 60.00 38 41 \w -66.00 32.00 1.00 3.00 -- -40.45 37.00-150.00 98 42 \w -110.00 -61.00 1.00 3.00 -- -40.45-155.00 148.00 49 ; _diffrn_measurement_device 'kappa diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0850853000 _diffrn_orient_matrix_UB_12 -0.0157221000 _diffrn_orient_matrix_UB_13 -0.0334424000 _diffrn_orient_matrix_UB_21 0.0179023000 _diffrn_orient_matrix_UB_22 0.0130888000 _diffrn_orient_matrix_UB_23 -0.1508174000 _diffrn_orient_matrix_UB_31 0.0108382000 _diffrn_orient_matrix_UB_32 -0.1472813000 _diffrn_orient_matrix_UB_33 -0.0098907000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0422 _diffrn_reflns_av_unetI/netI 0.0287 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 16856 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 66.500 _diffrn_reflns_theta_max 67.486 _diffrn_reflns_theta_min 4.443 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_current 0.80 _diffrn_source_power 0.040 _diffrn_source_target Cu _diffrn_source_type 'SuperNova (Cu) X-ray Source' _diffrn_source_voltage 50 _exptl_absorpt_coefficient_mu 0.812 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.74746 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 780 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.115 _refine_diff_density_min -0.173 _refine_diff_density_rms 0.030 _refine_ls_abs_structure_details ; Flack x determined using 1210 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.08(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 289 _refine_ls_number_reflns 3259 _refine_ls_number_restraints 55 _refine_ls_restrained_S_all 1.028 _refine_ls_R_factor_all 0.0342 _refine_ls_R_factor_gt 0.0312 _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^)+(0.0340P)^2^+0.2270P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0715 _refine_ls_wR_factor_ref 0.0729 _reflns_Friedel_coverage 0.733 _reflns_Friedel_fraction_full 0.994 _reflns_Friedel_fraction_max 0.994 _reflns_number_gt 3057 _reflns_number_total 3259 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ce01875d2.cif _cod_data_source_block cpd8_madiha38cult _cod_original_cell_volume 1812.89(12) _cod_database_code 7229945 _shelx_shelxl_version_number 2014/7 _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 99.95 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 68.13 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2. Restrained distances C22-C21 \\sim C23-C22 \\sim C24-C23 \\sim C24-C25 \\sim C25-C26 \\sim C26-C27 with sigma of 0.02 C21-C23 \\sim C25-C27 with sigma of 0.02 C22-C24 \\sim C23-C25 with sigma of 0.02 C23-C25 \\sim C24-C26 with sigma of 0.02 3. Rigid body (RIGU) restrains O22, O23, C26, C27 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.001 O20, O21, C21, C22 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.001 4. Others Fixed Sof: O20(0.5) O21(0.5) H21(0.5) O22(0.5) H22(0.5) O23(0.5) C21(0.5) C22(0.5) H22A(0.5) H22B(0.5) C23(0.5) H23A(0.5) H23B(0.5) C24(0.5) H24A(0.5) H24B(0.5) C25(0.5) H25A(0.5) H25B(0.5) C26(0.5) H26A(0.5) H26B(0.5) C27(0.5) 5.a Ternary CH refined with riding coordinates: C2(H2), C6(H6), C9(H9), C11(H11A), C12(H12) 5.b Secondary CH2 refined with riding coordinates: C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C22(H22A,H22B), C23(H23A, H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B) 5.c Idealised Me refined as rotating group: C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C) 5.d Idealised tetrahedral OH refined as rotating group: O21(H21), O22(H22) ; _shelx_res_file ; madiha38cult.res created by SHELXL-2014/7 TITL madiha38CuLT in P21212 #18 REM reset to P21212 #18 REM RIGU 0.01 0.001 O20 O21 H21 O23 O22 H22 C21 C22 C23 C24 C25 C26 C27 CELL 1.54184 17.58357 10.35942 9.95242 90 90 90 ZERR 2 0.00066 0.00043 0.00032 0 0 0 LATT -1 SYMM -X,-Y,+Z SYMM 0.5+X,0.5-Y,-Z SYMM 0.5-X,0.5+Y,-Z SFAC C H N O UNIT 74 116 4 24 EQIV $1 +X,-1+Y,+Z EQIV $2 1-X,-Y,+Z EQIV $3 +X,1+Y,+Z SADI C22 C21 C23 C22 C24 C23 C24 C25 C25 C26 C26 C27 SADI C21 C23 C25 C27 SADI C22 C24 C23 C25 SADI C23 C25 C24 C26 RIGU 0.003 0.001 O22 O23 C26 C27 RIGU 0.003 0.001 O20 O21 C21 C22 L.S. 8 PLAN 20 TEMP -173 HTAB N11 O20_$1 HTAB N11 O23_$2 HTAB O21 O10_$3 HTAB O22 O10_$2 HTAB BOND CONF fmap 2 acta 133 OMIT 0 135 OMIT 7 0 2 OMIT 10 2 10 OMIT -5 5 7 OMIT -10 2 10 OMIT 7 3 0 OMIT 1 3 4 OMIT 0 5 8 OMIT 5 3 10 OMIT 3 1 0 OMIT 10 10 4 OMIT -2 2 1 OMIT 2 0 2 OMIT 10 0 0 OMIT 2 12 1 OMIT 5 3 11 OMIT 10 7 2 OMIT 2 4 0 REM REM REM WGHT 0.034000 0.227000 FVAR 6.49166 O1 4 0.734768 0.194749 0.188570 11.00000 0.03131 0.02023 = 0.03361 -0.00027 0.00157 0.00180 O2 4 0.705984 0.061793 0.174888 11.00000 0.04384 0.01812 = 0.03393 -0.00206 -0.00235 0.00342 O3 4 0.578627 0.116293 0.178042 11.00000 0.03808 0.02275 = 0.04344 -0.00580 -0.00567 -0.00508 O10 4 0.662702 0.132829 0.608573 11.00000 0.05534 0.02605 = 0.02971 -0.00207 0.00846 -0.01618 N11 3 0.612699 0.153604 0.401610 11.00000 0.03205 0.02117 = 0.03681 -0.00371 0.00596 -0.00935 H11 2 0.580165 0.095499 0.423425 11.00000 0.05627 C1 1 0.674250 0.284571 0.224188 11.00000 0.02601 0.01753 = 0.03122 -0.00051 -0.00165 0.00105 C2 1 0.603070 0.212076 0.269300 11.00000 0.02878 0.01924 = 0.03926 -0.00463 -0.00257 -0.00200 AFIX 13 H2 2 0.561149 0.276899 0.276890 11.00000 -1.20000 AFIX 0 C3 1 0.638984 0.065538 0.096081 11.00000 0.04575 0.02402 = 0.03473 -0.00438 -0.00645 0.00091 C4 1 0.649112 0.147402 -0.030699 11.00000 0.06500 0.03120 = 0.03019 0.00046 -0.01039 -0.00383 AFIX 23 H4A 2 0.703590 0.147196 -0.055815 11.00000 -1.20000 H4B 2 0.620502 0.106469 -0.105027 11.00000 -1.20000 AFIX 0 C5 1 0.622632 0.287434 -0.016705 11.00000 0.05926 0.02804 = 0.04241 0.00549 -0.02214 -0.00691 AFIX 23 H5A 2 0.566848 0.287243 -0.003226 11.00000 -1.20000 H5B 2 0.632864 0.332376 -0.102611 11.00000 -1.20000 AFIX 0 C6 1 0.611132 0.487924 0.129536 11.00000 0.03645 0.02079 = 0.06467 0.00585 -0.02252 -0.00315 AFIX 13 H6 2 0.558745 0.458614 0.154003 11.00000 -1.20000 AFIX 0 C7 1 0.643362 0.562786 0.249418 11.00000 0.03285 0.01770 = 0.05784 0.00117 -0.01124 0.00093 AFIX 23 H7A 2 0.692594 0.601786 0.223318 11.00000 -1.20000 H7B 2 0.608073 0.633857 0.272550 11.00000 -1.20000 AFIX 0 C8 1 0.655250 0.478591 0.372546 11.00000 0.02705 0.01844 = 0.04591 -0.00336 -0.00167 -0.00073 AFIX 23 H8A 2 0.605536 0.445997 0.404626 11.00000 -1.20000 H8B 2 0.678280 0.530616 0.445395 11.00000 -1.20000 AFIX 0 C9 1 0.726600 0.278049 0.459899 11.00000 0.02543 0.01909 = 0.02972 0.00204 0.00240 -0.00072 AFIX 13 H9 2 0.771114 0.224497 0.431552 11.00000 -1.20000 AFIX 0 C10 1 0.664139 0.183915 0.495378 11.00000 0.03470 0.01796 = 0.02956 -0.00612 0.00577 -0.00242 C11 1 0.659010 0.366628 0.097689 11.00000 0.03941 0.02276 = 0.03702 0.00574 -0.01291 -0.00448 AFIX 13 H11A 2 0.709496 0.397398 0.064313 11.00000 -1.20000 AFIX 0 C12 1 0.707222 0.364697 0.339205 11.00000 0.02281 0.01769 = 0.03220 0.00041 -0.00163 -0.00102 AFIX 13 H12 2 0.756279 0.401829 0.306190 11.00000 -1.20000 AFIX 0 C13 1 0.619554 -0.074670 0.069887 11.00000 0.06695 0.02459 = 0.04132 -0.00583 -0.00604 -0.00162 AFIX 137 H13A 2 0.654854 -0.110156 0.003239 11.00000 -1.50000 H13B 2 0.567407 -0.080845 0.035729 11.00000 -1.50000 H13C 2 0.623828 -0.123720 0.153745 11.00000 -1.50000 AFIX 0 C14 1 0.604367 0.577073 0.008558 11.00000 0.07270 0.02528 = 0.07783 0.01145 -0.04941 -0.00669 AFIX 137 H14A 2 0.655010 0.607873 -0.017184 11.00000 -1.50000 H14B 2 0.572093 0.650933 0.031668 11.00000 -1.50000 H14C 2 0.581643 0.529812 -0.066702 11.00000 -1.50000 AFIX 0 C15 1 0.752419 0.352737 0.584606 11.00000 0.03658 0.02600 = 0.03291 0.00372 -0.00379 -0.00754 AFIX 137 H15A 2 0.709208 0.400406 0.622099 11.00000 -1.50000 H15B 2 0.792713 0.413527 0.559619 11.00000 -1.50000 H15C 2 0.771860 0.292074 0.651905 11.00000 -1.50000 AFIX 0 PART -1 O20 4 0.550180 0.864576 0.494365 10.50000 0.04106 0.02835 = 0.02595 0.00326 -0.00814 -0.01005 O21 4 0.587961 0.935002 0.696320 10.50000 0.03066 0.02216 = 0.02215 0.00632 -0.00539 -0.00507 AFIX 147 H21 2 0.599921 1.000766 0.651696 10.50000 -1.50000 AFIX 0 O22 4 0.402529 0.065281 0.714119 10.50000 0.02994 0.02010 = 0.02086 0.00267 0.01035 -0.01023 AFIX 147 H22 2 0.381603 0.002905 0.674860 10.50000 -1.50000 AFIX 0 O23 4 0.444147 0.114720 0.508818 10.50000 0.04907 0.03602 = 0.01950 -0.00062 0.01213 -0.02406 C21 1 0.556275 0.846988 0.614414 10.50000 0.01962 0.02958 = 0.03435 -0.00488 -0.00858 -0.01030 C22 1 0.552330 0.718681 0.688739 10.50000 0.03218 0.02303 = 0.02452 0.00090 -0.00078 -0.00369 AFIX 23 H22A 2 0.528414 0.732621 0.777616 10.50000 -1.20000 H22B 2 0.604640 0.686562 0.704097 10.50000 -1.20000 AFIX 0 C23 1 0.507195 0.616256 0.612189 10.50000 0.02832 0.01901 = 0.02965 -0.00492 0.00066 -0.00464 AFIX 23 H23A 2 0.452555 0.639280 0.613315 10.50000 -1.20000 H23B 2 0.524211 0.614481 0.517385 10.50000 -1.20000 AFIX 0 C24 1 0.517587 0.483570 0.673584 10.50000 0.02989 0.01971 = 0.02196 0.00025 -0.00095 -0.00344 AFIX 23 H24A 2 0.505112 0.488995 0.770420 10.50000 -1.20000 H24B 2 0.571936 0.459613 0.666312 10.50000 -1.20000 AFIX 0 C25 1 0.470279 0.375880 0.611727 10.50000 0.02430 0.01644 = 0.02168 -0.00384 -0.00341 -0.00487 AFIX 23 H25A 2 0.484873 0.364411 0.516398 10.50000 -1.20000 H25B 2 0.415780 0.399695 0.614789 10.50000 -1.20000 AFIX 0 C26 1 0.482453 0.249014 0.687706 10.50000 0.02961 0.01992 = 0.02014 0.00251 -0.00014 -0.00491 AFIX 23 H26A 2 0.467495 0.260552 0.782850 10.50000 -1.20000 H26B 2 0.537074 0.225933 0.685420 10.50000 -1.20000 AFIX 0 C27 1 0.435675 0.139068 0.625757 10.50000 0.02264 0.01868 = 0.01618 0.00203 0.00154 -0.01264 HKLF 4 REM madiha38CuLT in P21212 #18 REM R1 = 0.0312 for 3057 Fo > 4sig(Fo) and 0.0342 for all 3259 data REM 289 parameters refined using 55 restraints END WGHT 0.0347 0.2264 REM Instructions for potential hydrogen bonds HTAB N11 O20_$1 EQIV $4 -x+1, -y+1, z HTAB N11 O20_$4 HTAB N11 O23 HTAB N11 O23_$2 EQIV $5 -x+1, -y, z-1 HTAB C4 O22_$5 EQIV $6 x+1/2, -y+1/2, -z+1 HTAB C12 O22_$6 HTAB O21 O10_$3 HTAB O22 O10_$2 HTAB C26 O10 REM Highest difference peak 0.115, deepest hole -0.173, 1-sigma level 0.030 Q1 1 0.6455 0.2369 0.2541 11.00000 0.05 0.11 Q2 1 0.6332 0.4258 0.1099 11.00000 0.05 0.11 Q3 1 0.6168 0.1980 0.4682 11.00000 0.05 0.10 Q4 1 0.7192 0.3198 0.3946 11.00000 0.05 0.10 Q5 1 0.4807 0.3130 0.6541 11.00000 0.05 0.10 Q6 1 0.6169 0.1645 0.5983 11.00000 0.05 0.09 Q7 1 0.7391 0.2866 -0.1187 11.00000 0.05 0.09 Q8 1 0.7343 0.3051 0.5308 11.00000 0.05 0.09 Q9 1 0.5000 0.5000 0.2795 10.50000 0.05 0.09 Q10 1 0.5428 0.5594 -0.0362 11.00000 0.05 0.09 Q11 1 0.7541 0.1982 0.4130 11.00000 0.05 0.09 Q12 1 0.5139 0.0934 0.2015 11.00000 0.05 0.08 Q13 1 0.6971 0.3196 0.2745 11.00000 0.05 0.08 Q14 1 0.5244 -0.0181 0.2727 11.00000 0.05 0.08 Q15 1 0.6441 0.3274 0.0391 11.00000 0.05 0.08 Q16 1 0.5449 0.7573 0.1108 11.00000 0.05 0.08 Q17 1 0.6948 0.2387 0.4653 11.00000 0.05 0.08 Q18 1 0.7622 0.1560 0.0000 11.00000 0.05 0.08 Q19 1 0.6094 0.5420 0.0642 11.00000 0.05 0.08 Q20 1 0.5231 0.5564 0.6399 11.00000 0.05 0.08 ; _shelx_res_checksum 72915 _olex2_date_sample_data_collection 2017-07-11 _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 1.449 _oxdiff_exptl_absorpt_empirical_full_min 0.679 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -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 O1 O 0.73477(8) 0.19475(15) 0.18857(15) 0.0284(3) Uani 1 1 d . . . . . O2 O 0.70598(9) 0.06179(15) 0.17489(16) 0.0320(4) Uani 1 1 d . . . . . O3 O 0.57863(9) 0.11629(16) 0.17804(17) 0.0348(4) Uani 1 1 d . . . . . O10 O 0.66270(10) 0.13283(16) 0.60857(15) 0.0370(4) Uani 1 1 d . . . . . N11 N 0.61270(11) 0.15360(19) 0.4016(2) 0.0300(4) Uani 1 1 d . . . . . H11 H 0.5802(19) 0.095(3) 0.423(3) 0.056(10) Uiso 1 1 d . . . . . C1 C 0.67425(12) 0.2846(2) 0.2242(2) 0.0249(4) Uani 1 1 d . . . . . C2 C 0.60307(13) 0.2121(2) 0.2693(2) 0.0291(5) Uani 1 1 d . . . . . H2 H 0.5611 0.2769 0.2769 0.035 Uiso 1 1 calc R . . . . C3 C 0.63898(15) 0.0655(2) 0.0961(2) 0.0348(5) Uani 1 1 d . . . . . C4 C 0.64911(18) 0.1474(3) -0.0307(2) 0.0421(6) Uani 1 1 d . . . . . H4A H 0.7036 0.1472 -0.0558 0.051 Uiso 1 1 calc R . . . . H4B H 0.6205 0.1065 -0.1050 0.051 Uiso 1 1 calc R . . . . C5 C 0.62263(17) 0.2874(3) -0.0167(3) 0.0432(6) Uani 1 1 d . . . . . H5A H 0.5668 0.2872 -0.0032 0.052 Uiso 1 1 calc R . . . . H5B H 0.6329 0.3324 -0.1026 0.052 Uiso 1 1 calc R . . . . C6 C 0.61113(15) 0.4879(2) 0.1295(3) 0.0406(6) Uani 1 1 d . . . . . H6 H 0.5587 0.4586 0.1540 0.049 Uiso 1 1 calc R . . . . C7 C 0.64336(14) 0.5628(2) 0.2494(3) 0.0361(6) Uani 1 1 d . . . . . H7A H 0.6926 0.6018 0.2233 0.043 Uiso 1 1 calc R . . . . H7B H 0.6081 0.6339 0.2726 0.043 Uiso 1 1 calc R . . . . C8 C 0.65525(12) 0.4786(2) 0.3725(2) 0.0305(5) Uani 1 1 d . . . . . H8A H 0.6055 0.4460 0.4046 0.037 Uiso 1 1 calc R . . . . H8B H 0.6783 0.5306 0.4454 0.037 Uiso 1 1 calc R . . . . C9 C 0.72660(12) 0.2780(2) 0.4599(2) 0.0247(4) Uani 1 1 d . . . . . H9 H 0.7711 0.2245 0.4316 0.030 Uiso 1 1 calc R . . . . C10 C 0.66414(13) 0.1839(2) 0.4954(2) 0.0274(5) Uani 1 1 d . . . . . C11 C 0.65901(14) 0.3666(2) 0.0977(2) 0.0331(5) Uani 1 1 d . . . . . H11A H 0.7095 0.3974 0.0643 0.040 Uiso 1 1 calc R . . . . C12 C 0.70722(11) 0.3647(2) 0.3392(2) 0.0242(4) Uani 1 1 d . . . . . H12 H 0.7563 0.4018 0.3062 0.029 Uiso 1 1 calc R . . . . C13 C 0.61955(17) -0.0747(3) 0.0699(3) 0.0443(6) Uani 1 1 d . . . . . H13A H 0.6549 -0.1102 0.0032 0.066 Uiso 1 1 calc GR . . . . H13B H 0.5674 -0.0808 0.0357 0.066 Uiso 1 1 calc GR . . . . H13C H 0.6238 -0.1237 0.1537 0.066 Uiso 1 1 calc GR . . . . C14 C 0.60437(19) 0.5771(3) 0.0086(3) 0.0586(9) Uani 1 1 d . . . . . H14A H 0.6550 0.6079 -0.0172 0.088 Uiso 1 1 calc GR . . . . H14B H 0.5721 0.6509 0.0317 0.088 Uiso 1 1 calc GR . . . . H14C H 0.5816 0.5298 -0.0667 0.088 Uiso 1 1 calc GR . . . . C15 C 0.75242(13) 0.3527(2) 0.5846(2) 0.0318(5) Uani 1 1 d . . . . . H15A H 0.7092 0.4004 0.6221 0.048 Uiso 1 1 calc GR . . . . H15B H 0.7927 0.4135 0.5596 0.048 Uiso 1 1 calc GR . . . . H15C H 0.7719 0.2921 0.6519 0.048 Uiso 1 1 calc GR . . . . O20 O 0.5502(11) 0.8646(14) 0.4944(14) 0.0318(19) Uani 0.5 1 d . U P A -1 O21 O 0.5880(12) 0.9350(19) 0.6963(16) 0.0250(19) Uani 0.5 1 d . U P A -1 H21 H 0.5999 1.0008 0.6517 0.037 Uiso 0.5 1 calc GR . P A -1 O22 O 0.4025(12) 0.0653(18) 0.7141(16) 0.024(2) Uani 0.5 1 d . U P A -1 H22 H 0.3816 0.0029 0.6749 0.035 Uiso 0.5 1 calc GR . P A -1 O23 O 0.4441(12) 0.1147(15) 0.5088(14) 0.035(2) Uani 0.5 1 d . U P A -1 C21 C 0.5563(13) 0.8470(14) 0.614(2) 0.028(3) Uani 0.5 1 d D U P A -1 C22 C 0.5523(3) 0.7187(5) 0.6887(5) 0.0266(11) Uani 0.5 1 d D U P A -1 H22A H 0.5284 0.7326 0.7776 0.032 Uiso 0.5 1 calc R . P A -1 H22B H 0.6046 0.6866 0.7041 0.032 Uiso 0.5 1 calc R . P A -1 C23 C 0.5072(6) 0.6163(10) 0.6122(15) 0.026(2) Uani 0.5 1 d D . P A -1 H23A H 0.4526 0.6393 0.6133 0.031 Uiso 0.5 1 calc R . P A -1 H23B H 0.5242 0.6145 0.5174 0.031 Uiso 0.5 1 calc R . P A -1 C24 C 0.5176(2) 0.4836(5) 0.6736(4) 0.0238(11) Uani 0.5 1 d D . P A -1 H24A H 0.5051 0.4890 0.7704 0.029 Uiso 0.5 1 calc R . P A -1 H24B H 0.5719 0.4596 0.6663 0.029 Uiso 0.5 1 calc R . P A -1 C25 C 0.4703(6) 0.3759(9) 0.6117(14) 0.021(2) Uani 0.5 1 d D . P A -1 H25A H 0.4849 0.3644 0.5164 0.025 Uiso 0.5 1 calc R . P A -1 H25B H 0.4158 0.3997 0.6148 0.025 Uiso 0.5 1 calc R . P A -1 C26 C 0.4825(3) 0.2490(5) 0.6877(5) 0.0232(10) Uani 0.5 1 d D U P A -1 H26A H 0.4675 0.2606 0.7828 0.028 Uiso 0.5 1 calc R . P A -1 H26B H 0.5371 0.2259 0.6854 0.028 Uiso 0.5 1 calc R . P A -1 C27 C 0.4357(12) 0.1391(13) 0.6258(16) 0.019(2) Uani 0.5 1 d D U P A -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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0313(8) 0.0202(8) 0.0336(8) -0.0003(7) 0.0016(6) 0.0018(6) O2 0.0438(8) 0.0181(8) 0.0339(8) -0.0021(6) -0.0023(7) 0.0034(7) O3 0.0381(8) 0.0228(8) 0.0434(9) -0.0058(7) -0.0057(7) -0.0051(7) O10 0.0553(10) 0.0261(9) 0.0297(8) -0.0021(7) 0.0085(7) -0.0162(8) N11 0.0320(10) 0.0212(10) 0.0368(10) -0.0037(8) 0.0060(8) -0.0094(8) C1 0.0260(10) 0.0175(10) 0.0312(10) -0.0005(9) -0.0017(8) 0.0010(9) C2 0.0288(11) 0.0192(11) 0.0393(12) -0.0046(9) -0.0026(9) -0.0020(9) C3 0.0457(13) 0.0240(12) 0.0347(12) -0.0044(10) -0.0065(10) 0.0009(10) C4 0.0650(17) 0.0312(14) 0.0302(12) 0.0005(10) -0.0104(11) -0.0038(13) C5 0.0593(16) 0.0280(13) 0.0424(14) 0.0055(11) -0.0221(12) -0.0069(12) C6 0.0364(12) 0.0208(12) 0.0647(17) 0.0059(12) -0.0225(12) -0.0032(10) C7 0.0329(12) 0.0177(11) 0.0578(16) 0.0012(11) -0.0112(11) 0.0009(9) C8 0.0271(10) 0.0184(11) 0.0459(13) -0.0034(10) -0.0017(10) -0.0007(8) C9 0.0254(10) 0.0191(11) 0.0297(11) 0.0020(9) 0.0024(8) -0.0007(8) C10 0.0347(11) 0.0180(10) 0.0296(11) -0.0061(9) 0.0058(9) -0.0024(8) C11 0.0394(12) 0.0228(12) 0.0370(12) 0.0057(11) -0.0129(10) -0.0045(10) C12 0.0228(9) 0.0177(10) 0.0322(10) 0.0004(9) -0.0016(8) -0.0010(8) C13 0.0670(17) 0.0246(13) 0.0413(14) -0.0058(11) -0.0060(13) -0.0016(12) C14 0.0727(19) 0.0253(14) 0.078(2) 0.0114(14) -0.0494(18) -0.0067(13) C15 0.0366(12) 0.0260(12) 0.0329(11) 0.0037(10) -0.0038(10) -0.0075(10) O20 0.041(4) 0.028(4) 0.026(3) 0.003(3) -0.008(2) -0.010(3) O21 0.031(5) 0.022(3) 0.022(4) 0.006(2) -0.005(3) -0.005(2) O22 0.030(4) 0.020(3) 0.021(3) 0.003(2) 0.010(2) -0.010(3) O23 0.049(4) 0.036(5) 0.019(3) -0.001(2) 0.012(2) -0.024(3) C21 0.020(4) 0.030(5) 0.034(4) -0.005(3) -0.009(3) -0.010(3) C22 0.032(3) 0.023(2) 0.025(2) 0.0009(17) -0.001(2) -0.004(2) C23 0.028(6) 0.019(3) 0.030(3) -0.005(2) 0.001(4) -0.005(3) C24 0.030(3) 0.020(3) 0.0220(17) 0.0002(18) -0.0010(16) -0.003(2) C25 0.024(5) 0.016(3) 0.022(3) -0.004(2) -0.003(4) -0.005(3) C26 0.030(3) 0.020(2) 0.020(2) 0.0025(17) 0.000(2) -0.0049(19) C27 0.023(5) 0.019(4) 0.016(3) 0.002(3) 0.002(3) -0.013(3) 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_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 O1 O2 111.62(14) C3 O2 O1 108.14(16) C2 O3 C3 113.40(17) C10 N11 C2 127.65(19) O1 C1 C2 110.85(17) O1 C1 C11 106.27(18) O1 C1 C12 104.59(16) C2 C1 C11 111.63(18) C2 C1 C12 110.97(18) C12 C1 C11 112.20(17) O3 C2 N11 108.90(18) O3 C2 C1 113.95(18) N11 C2 C1 111.98(18) O2 C3 O3 108.05(18) O2 C3 C4 112.0(2) O2 C3 C13 104.9(2) O3 C3 C4 110.5(2) O3 C3 C13 106.4(2) C13 C3 C4 114.6(2) C5 C4 C3 114.5(2) C4 C5 C11 116.4(2) C7 C6 C11 111.71(19) C14 C6 C7 109.7(2) C14 C6 C11 111.9(2) C8 C7 C6 112.87(19) C7 C8 C12 110.51(19) C10 C9 C12 113.47(18) C10 C9 C15 110.63(18) C15 C9 C12 113.82(17) O10 C10 N11 121.2(2) O10 C10 C9 120.0(2) N11 C10 C9 118.7(2) C1 C11 C6 112.0(2) C5 C11 C1 112.42(19) C5 C11 C6 111.0(2) C1 C12 C8 110.79(17) C1 C12 C9 110.62(17) C8 C12 C9 114.42(18) O20 C21 O21 122.1(13) O20 C21 C22 127.3(13) O21 C21 C22 108.4(14) C21 C22 C23 112.8(9) C24 C23 C22 111.5(9) C23 C24 C25 115.8(5) C24 C25 C26 110.7(8) C25 C26 C27 111.3(9) O22 C27 C26 113.8(12) O23 C27 O22 125.9(13) O23 C27 C26 118.6(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 O2 1.474(2) O1 C1 1.457(3) O2 C3 1.416(3) O3 C2 1.412(3) O3 C3 1.438(3) O10 C10 1.245(3) N11 C2 1.459(3) N11 C10 1.337(3) C1 C2 1.527(3) C1 C11 1.543(3) C1 C12 1.528(3) C3 C4 1.531(3) C3 C13 1.515(3) C4 C5 1.530(4) C5 C11 1.542(3) C6 C7 1.532(3) C6 C11 1.545(4) C6 C14 1.522(4) C7 C8 1.519(3) C8 C12 1.529(3) C9 C10 1.511(3) C9 C12 1.538(3) C9 C15 1.531(3) O20 C21 1.213(19) O21 C21 1.344(16) O22 C27 1.303(15) O23 C27 1.200(17) C21 C22 1.523(14) C22 C23 1.528(11) C23 C24 1.515(12) C24 C25 1.522(10) C25 C26 1.531(12) C26 C27 1.534(12) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N11 H11 O20 0.86(3) 2.55(4) 3.320(14) 150(3) 1_545 N11 H11 O23 0.86(3) 2.38(4) 3.141(15) 149(3) 2_655 O21 H21 O10 0.84 1.81 2.586(17) 153.0 1_565 O22 H22 O10 0.84 1.74 2.575(17) 174.6 2_655 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 O1 O2 C3 O3 -74.8(2) O1 O2 C3 C4 47.2(2) O1 O2 C3 C13 172.06(18) O1 C1 C2 O3 -51.9(2) O1 C1 C2 N11 72.3(2) O1 C1 C11 C5 68.6(2) O1 C1 C11 C6 -165.57(18) O1 C1 C12 C8 170.60(17) O1 C1 C12 C9 -61.4(2) O2 O1 C1 C2 13.4(2) O2 O1 C1 C11 -108.07(17) O2 O1 C1 C12 133.07(16) O2 C3 C4 C5 -95.0(3) O3 C3 C4 C5 25.6(3) C1 O1 O2 C3 46.8(2) C2 O3 C3 O2 35.2(3) C2 O3 C3 C4 -87.7(2) C2 O3 C3 C13 147.3(2) C2 N11 C10 O10 174.6(2) C2 N11 C10 C9 -7.9(3) C2 C1 C11 C5 -52.3(3) C2 C1 C11 C6 73.5(2) C2 C1 C12 C8 -69.8(2) C2 C1 C12 C9 58.2(2) C3 O3 C2 N11 -99.7(2) C3 O3 C2 C1 26.1(3) C3 C4 C5 C11 56.4(3) C4 C5 C11 C1 -35.8(3) C4 C5 C11 C6 -162.2(2) C6 C7 C8 C12 56.6(3) C7 C6 C11 C1 49.5(3) C7 C6 C11 C5 176.0(2) C7 C8 C12 C1 -57.6(2) C7 C8 C12 C9 176.52(18) C10 N11 C2 O3 146.1(2) C10 N11 C2 C1 19.2(3) C10 C9 C12 C1 -46.4(2) C10 C9 C12 C8 79.5(2) C11 C1 C2 O3 66.4(2) C11 C1 C2 N11 -169.44(18) C11 C1 C12 C8 55.8(2) C11 C1 C12 C9 -176.20(18) C11 C6 C7 C8 -52.6(3) C12 C1 C2 O3 -167.64(18) C12 C1 C2 N11 -43.5(2) C12 C1 C11 C5 -177.6(2) C12 C1 C11 C6 -51.8(2) C12 C9 C10 O10 -161.1(2) C12 C9 C10 N11 21.3(3) C13 C3 C4 C5 145.7(2) C14 C6 C7 C8 -177.3(2) C14 C6 C11 C1 173.0(2) C14 C6 C11 C5 -60.4(3) C15 C9 C10 O10 -31.7(3) C15 C9 C10 N11 150.7(2) C15 C9 C12 C1 -174.14(17) C15 C9 C12 C8 -48.2(2) O20 C21 C22 C23 -25(3) O21 C21 C22 C23 172.0(14) C21 C22 C23 C24 168.4(12) C22 C23 C24 C25 175.5(9) C23 C24 C25 C26 -176.7(9) C24 C25 C26 C27 -179.5(10) C25 C26 C27 O22 -137.4(15) C25 C26 C27 O23 56(2)