#------------------------------------------------------------------------------ #$Date: 2024-10-30 04:36:09 +0200 (Wed, 30 Oct 2024) $ #$Revision: 295675 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/29/1572974.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_1572974 loop_ _publ_author_name 'Fu, Shijie' 'Jia, Hao' 'Meng, Xinmiao' 'Wang, Chengyuan' 'Li, Qian' 'Li, Lei' 'Yang, Jiaxiang' 'Niu, Helin' _publ_section_title ; Fine-tuning the molecular conformation and packing structures of coumarin-based luminogens to achieve distinct piezochromic properties upon mechanical grinding and under hydrostatic pressures. ; _journal_name_full 'Materials horizons' _journal_paper_doi 10.1039/d4mh01343c _journal_year 2024 _chemical_formula_moiety 'C20 H18 N2 O2' _chemical_formula_sum 'C20 H18 N2 O2' _chemical_formula_weight 318.36 _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 _audit_creation_date 2024-10-13 _audit_creation_method ; Olex2 1.5 (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498) ; _audit_update_record ; 2024-10-22 deposited with the CCDC. 2024-10-22 downloaded from the CCDC. ; _cell_angle_alpha 79.488(7) _cell_angle_beta 81.308(7) _cell_angle_gamma 64.528(7) _cell_formula_units_Z 2 _cell_length_a 6.6330(6) _cell_length_b 7.5002(7) _cell_length_c 17.4918(16) _cell_measurement_reflns_used 5269 _cell_measurement_temperature 120.00 _cell_measurement_theta_max 68.36 _cell_measurement_theta_min 5.16 _cell_volume 769.83(13) _computing_cell_refinement 'X-Area Recipe 1.37.0.0 (STOE, 2021)' _computing_data_collection 'X-Area Pilatus3_SV 1.31.175.0 (STOE, 2021)' _computing_data_reduction ; X-Area Integrate 2.5.1.0 (STOE, 2021) X-Area LANA 2.6.2.0 (STOE, 2021) ; _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'olex2.solve 1.5 (Bourhis et al., 2015)' _diffrn_ambient_temperature 120.00 _diffrn_detector_area_resol_mean 5.81 _diffrn_measured_fraction_theta_full 0.976 _diffrn_measured_fraction_theta_max 0.976 _diffrn_measurement_device_type 'STOE STADIVARI' _diffrn_measurement_method 'rotation method, \w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54186 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_unetI/netI 0.0327 _diffrn_reflns_Laue_measured_fraction_full 0.976 _diffrn_reflns_Laue_measured_fraction_max 0.976 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 2488 _diffrn_reflns_point_group_measured_fraction_full 0.976 _diffrn_reflns_point_group_measured_fraction_max 0.976 _diffrn_reflns_theta_full 63.996 _diffrn_reflns_theta_max 63.996 _diffrn_reflns_theta_min 5.161 _exptl_absorpt_coefficient_mu 0.718 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 1.0000 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.373 _exptl_crystal_description block _exptl_crystal_F_000 336 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _refine_diff_density_max 0.423 _refine_diff_density_min -0.370 _refine_diff_density_rms 0.095 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.202 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 220 _refine_ls_number_reflns 2488 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.202 _refine_ls_R_factor_all 0.0993 _refine_ls_R_factor_gt 0.0894 _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^)+(0.0998P)^2^+2.7580P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2840 _refine_ls_wR_factor_ref 0.2880 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2056 _reflns_number_total 2488 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4mh01343c2.cif _cod_data_source_block 7_tw _cod_database_code 1572974 _shelx_shelxl_version_number 2018/3 _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. ; _olex2_refinement_description ; 1. Twinned data refinement Scales: 0.851(7) 0.149(7) 2. 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 3.a Secondary CH2 refined with riding coordinates: C00F(H00D,H00E), C00M(H00F,H00M) 3.b Aromatic/amide H refined with riding coordinates: C009(H009), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00N(H00N) 3.c Idealised Me refined as rotating group: C006(H00A,H00B,H00C), C00O(H00O,H00P,H00Q) ; _shelx_res_file ; TITL 7_a.res in P-1 7_tw.res created by SHELXL-2018/3 at 09:44:09 on 13-Oct-2024 REM Old TITL REM SHELXT solution in P-1 REM R1 0.168, Rweak 0.014, Alpha 0.111, Orientation as input REM Formula found by SHELXT: C20 N2 O2 CELL 1.54186 6.633 7.5002 17.4918 79.488 81.308 64.528 ZERR 2 0.0006 0.0007 0.0016 0.007 0.007 0.007 LATT 1 SFAC C H N O UNIT 40 36 4 4 L.S. 10 0 0 PLAN 5 TEMP -153.15 CONF LIST 4 MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.099800 2.758000 BASF 0.14899 FVAR 10.63211 O001 4 0.797961 0.328768 0.400666 11.00000 0.01701 0.03028 = 0.02376 0.00033 -0.00556 -0.01134 O002 4 0.939478 0.226686 0.513667 11.00000 0.02136 0.04217 = 0.02448 0.00307 -0.00880 -0.01745 N003 3 0.532570 0.603450 0.148627 11.00000 0.01971 0.02394 = 0.02266 -0.00069 -0.00219 -0.00782 N004 3 0.439665 -0.145117 0.895233 11.00000 0.03437 0.03372 = 0.02745 0.00283 -0.00570 -0.01448 C005 1 0.486542 -0.003136 0.750714 11.00000 0.02847 0.02012 = 0.02097 -0.00287 -0.00384 -0.01037 C006 1 0.916611 0.398494 0.094308 11.00000 0.02504 0.03128 = 0.02820 -0.00267 -0.00121 -0.01124 AFIX 137 H00A 2 0.854755 0.358347 0.056386 11.00000 -1.50000 H00B 2 0.944634 0.300358 0.141329 11.00000 -1.50000 H00C 2 1.057558 0.405916 0.071481 11.00000 -1.50000 AFIX 0 C007 1 0.426398 0.378442 0.382581 11.00000 0.02286 0.02031 = 0.02610 -0.00293 -0.00509 -0.01174 C008 1 0.628832 0.390187 0.352093 11.00000 0.01832 0.01726 = 0.02680 -0.00263 -0.00656 -0.00631 C009 1 0.258155 0.448525 0.330458 11.00000 0.01807 0.02498 = 0.02947 -0.00692 -0.00186 -0.01037 AFIX 43 H009 2 0.117737 0.444019 0.348489 11.00000 -1.20000 AFIX 0 C00A 1 0.572892 0.235914 0.510749 11.00000 0.02243 0.01990 = 0.02489 -0.00238 -0.00517 -0.00942 C00B 1 0.780607 0.259783 0.478630 11.00000 0.02040 0.02133 = 0.02069 -0.00048 -0.00411 -0.00806 C00C 1 0.546745 0.152953 0.593399 11.00000 0.02169 0.01940 = 0.02394 -0.00598 -0.00343 -0.01015 C00D 1 0.500162 0.530950 0.223829 11.00000 0.02497 0.01697 = 0.02523 -0.00306 -0.00335 -0.00899 C00E 1 0.459823 -0.083662 0.830813 11.00000 0.02113 0.02531 = 0.02770 -0.00001 -0.00616 -0.00999 C00F 1 0.750111 0.601903 0.115649 11.00000 0.02535 0.02917 = 0.02167 0.00168 -0.00237 -0.01605 AFIX 23 H00D 2 0.813426 0.641495 0.154016 11.00000 -1.20000 H00E 2 0.727784 0.701499 0.068378 11.00000 -1.20000 AFIX 0 C00G 1 0.291247 0.522510 0.254982 11.00000 0.02162 0.02357 = 0.02535 0.00089 -0.00922 -0.00784 AFIX 43 H00G 2 0.172511 0.569981 0.221935 11.00000 -1.20000 AFIX 0 C00H 1 0.669896 0.459889 0.276272 11.00000 0.02081 0.02093 = 0.02597 -0.00186 -0.00423 -0.00906 AFIX 43 H00H 2 0.812210 0.460745 0.258681 11.00000 -1.20000 AFIX 0 C00I 1 0.724233 0.067543 0.641893 11.00000 0.02124 0.02683 = 0.02785 -0.00201 -0.00462 -0.01089 AFIX 43 H00I 2 0.867768 0.061758 0.621569 11.00000 -1.20000 AFIX 0 C00J 1 0.339913 0.155446 0.626575 11.00000 0.02457 0.02783 = 0.02371 0.00017 -0.00929 -0.01078 AFIX 43 H00J 2 0.216844 0.211578 0.595095 11.00000 -1.20000 AFIX 0 C00K 1 0.307681 0.079570 0.703225 11.00000 0.02038 0.03212 = 0.02485 -0.00363 -0.00238 -0.01430 AFIX 43 H00K 2 0.164925 0.083481 0.723610 11.00000 -1.20000 AFIX 0 C00L 1 0.693555 -0.007880 0.718363 11.00000 0.02199 0.02571 = 0.02609 0.00071 -0.00719 -0.00838 AFIX 43 H00L 2 0.816604 -0.064581 0.749864 11.00000 -1.20000 AFIX 0 C00M 1 0.365847 0.656052 0.092580 11.00000 0.02569 0.02718 = 0.02091 -0.00195 -0.00674 -0.01006 AFIX 23 H00F 2 0.294084 0.561451 0.104809 11.00000 -1.20000 H00M 2 0.443112 0.641301 0.039557 11.00000 -1.20000 AFIX 0 C00N 1 0.406871 0.296531 0.461554 11.00000 0.01889 0.02231 = 0.02789 -0.00435 -0.00137 -0.01124 AFIX 43 H00N 2 0.271943 0.283023 0.481325 11.00000 -1.20000 AFIX 0 C00O 1 0.186388 0.865646 0.092870 11.00000 0.02919 0.03102 = 0.02967 0.00002 -0.00833 -0.00821 AFIX 137 H00O 2 0.077453 0.890124 0.055797 11.00000 -1.50000 H00P 2 0.255032 0.960752 0.077663 11.00000 -1.50000 H00Q 2 0.110200 0.882103 0.145338 11.00000 -1.50000 AFIX 0 HKLF 5 REM 7_a.res in P-1 REM wR2 = 0.2880, GooF = S = 1.202, Restrained GooF = 1.202 for all data REM R1 = 0.0894 for 2056 Fo > 4sig(Fo) and 0.0993 for all 2488 data REM 220 parameters refined using 0 restraints END WGHT 0.0998 2.7580 REM Highest difference peak 0.423, deepest hole -0.370, 1-sigma level 0.095 Q1 1 0.6403 0.3556 0.3002 11.00000 0.05 0.42 Q2 1 0.5599 0.2655 0.5621 11.00000 0.05 0.41 Q3 1 0.7717 0.2150 0.4187 11.00000 0.05 0.40 Q4 1 0.4564 -0.0963 0.7773 11.00000 0.05 0.40 Q5 1 0.5153 0.4847 0.1777 11.00000 0.05 0.38 ; _shelx_res_checksum 69578 _olex2_submission_special_instructions 'No special instructions were received' 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 0.7980(5) 0.3288(5) 0.40067(18) 0.0232(8) Uani 1 1 d . . . . . O002 O 0.9395(6) 0.2267(5) 0.51367(19) 0.0281(9) Uani 1 1 d . . . . . N003 N 0.5326(6) 0.6034(6) 0.1486(2) 0.0228(9) Uani 1 1 d . . . . . N004 N 0.4397(8) -0.1451(7) 0.8952(3) 0.0323(11) Uani 1 1 d . . . . . C005 C 0.4865(8) -0.0031(7) 0.7507(3) 0.0228(11) Uani 1 1 d . . . . . C006 C 0.9166(8) 0.3985(8) 0.0943(3) 0.0286(12) Uani 1 1 d . . . . . H00A H 0.854755 0.358347 0.056386 0.043 Uiso 1 1 calc R U . . . H00B H 0.944634 0.300358 0.141329 0.043 Uiso 1 1 calc R U . . . H00C H 1.057558 0.405916 0.071481 0.043 Uiso 1 1 calc R U . . . C007 C 0.4264(8) 0.3784(7) 0.3826(3) 0.0218(10) Uani 1 1 d . . . . . C008 C 0.6288(8) 0.3902(7) 0.3521(3) 0.0207(10) Uani 1 1 d . . . . . C009 C 0.2582(8) 0.4485(7) 0.3305(3) 0.0232(11) Uani 1 1 d . . . . . H009 H 0.117737 0.444019 0.348489 0.028 Uiso 1 1 calc R U . . . C00A C 0.5729(8) 0.2359(7) 0.5107(3) 0.0219(11) Uani 1 1 d . . . . . C00B C 0.7806(8) 0.2598(7) 0.4786(3) 0.0211(10) Uani 1 1 d . . . . . C00C C 0.5467(8) 0.1530(7) 0.5934(3) 0.0205(10) Uani 1 1 d . . . . . C00D C 0.5002(8) 0.5310(7) 0.2238(3) 0.0221(11) Uani 1 1 d . . . . . C00E C 0.4598(8) -0.0837(7) 0.8308(3) 0.0246(11) Uani 1 1 d . . . . . C00F C 0.7501(8) 0.6019(7) 0.1156(3) 0.0243(11) Uani 1 1 d . . . . . H00D H 0.813426 0.641495 0.154016 0.029 Uiso 1 1 calc R U . . . H00E H 0.727784 0.701499 0.068378 0.029 Uiso 1 1 calc R U . . . C00G C 0.2912(8) 0.5225(7) 0.2550(3) 0.0238(11) Uani 1 1 d . . . . . H00G H 0.172511 0.569981 0.221935 0.029 Uiso 1 1 calc R U . . . C00H C 0.6699(8) 0.4599(7) 0.2763(3) 0.0223(11) Uani 1 1 d . . . . . H00H H 0.812210 0.460745 0.258681 0.027 Uiso 1 1 calc R U . . . C00I C 0.7242(8) 0.0675(7) 0.6419(3) 0.0249(11) Uani 1 1 d . . . . . H00I H 0.867768 0.061758 0.621569 0.030 Uiso 1 1 calc R U . . . C00J C 0.3399(8) 0.1554(7) 0.6266(3) 0.0251(11) Uani 1 1 d . . . . . H00J H 0.216844 0.211578 0.595095 0.030 Uiso 1 1 calc R U . . . C00K C 0.3077(8) 0.0796(7) 0.7032(3) 0.0245(11) Uani 1 1 d . . . . . H00K H 0.164925 0.083481 0.723610 0.029 Uiso 1 1 calc R U . . . C00L C 0.6936(8) -0.0079(7) 0.7184(3) 0.0251(11) Uani 1 1 d . . . . . H00L H 0.816604 -0.064581 0.749864 0.030 Uiso 1 1 calc R U . . . C00M C 0.3658(8) 0.6561(7) 0.0926(3) 0.0245(11) Uani 1 1 d . . . . . H00F H 0.294084 0.561451 0.104809 0.029 Uiso 1 1 calc R U . . . H00M H 0.443112 0.641301 0.039557 0.029 Uiso 1 1 calc R U . . . C00N C 0.4069(8) 0.2965(7) 0.4616(3) 0.0220(11) Uani 1 1 d . . . . . H00N H 0.271943 0.283023 0.481325 0.026 Uiso 1 1 calc R U . . . C00O C 0.1864(9) 0.8656(8) 0.0929(3) 0.0314(12) Uani 1 1 d . . . . . H00O H 0.077453 0.890124 0.055797 0.047 Uiso 1 1 calc R U . . . H00P H 0.255032 0.960752 0.077663 0.047 Uiso 1 1 calc R U . . . H00Q H 0.110200 0.882103 0.145338 0.047 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 0.0170(17) 0.0303(19) 0.0238(18) 0.0003(14) -0.0056(13) -0.0113(14) O002 0.0214(18) 0.042(2) 0.0245(18) 0.0031(15) -0.0088(14) -0.0174(16) N003 0.020(2) 0.024(2) 0.023(2) -0.0007(16) -0.0022(16) -0.0078(17) N004 0.034(3) 0.034(3) 0.027(3) 0.0028(19) -0.0057(19) -0.014(2) C005 0.028(3) 0.020(2) 0.021(2) -0.0029(19) -0.0038(19) -0.010(2) C006 0.025(3) 0.031(3) 0.028(3) -0.003(2) -0.001(2) -0.011(2) C007 0.023(2) 0.020(2) 0.026(3) -0.0029(19) -0.0051(19) -0.012(2) C008 0.018(2) 0.017(2) 0.027(3) -0.0026(19) -0.0066(19) -0.0063(19) C009 0.018(2) 0.025(3) 0.029(3) -0.007(2) -0.0019(19) -0.010(2) C00A 0.022(3) 0.020(2) 0.025(3) -0.0024(19) -0.0052(19) -0.009(2) C00B 0.020(2) 0.021(2) 0.021(2) -0.0005(18) -0.0041(19) -0.008(2) C00C 0.022(2) 0.019(2) 0.024(2) -0.0060(19) -0.0034(19) -0.010(2) C00D 0.025(3) 0.017(2) 0.025(3) -0.0031(19) -0.0034(19) -0.009(2) C00E 0.021(3) 0.025(3) 0.028(3) 0.000(2) -0.0062(19) -0.010(2) C00F 0.025(3) 0.029(3) 0.022(2) 0.0017(19) -0.0024(19) -0.016(2) C00G 0.022(2) 0.024(3) 0.025(3) 0.001(2) -0.009(2) -0.008(2) C00H 0.021(2) 0.021(2) 0.026(3) -0.0019(19) -0.0042(19) -0.009(2) C00I 0.021(3) 0.027(3) 0.028(3) -0.002(2) -0.005(2) -0.011(2) C00J 0.025(3) 0.028(3) 0.024(3) 0.000(2) -0.009(2) -0.011(2) C00K 0.020(2) 0.032(3) 0.025(3) -0.004(2) -0.0024(19) -0.014(2) C00L 0.022(3) 0.026(3) 0.026(3) 0.001(2) -0.007(2) -0.008(2) C00M 0.026(3) 0.027(3) 0.021(2) -0.0020(19) -0.0067(19) -0.010(2) C00N 0.019(2) 0.022(2) 0.028(3) -0.004(2) -0.0014(19) -0.011(2) C00O 0.029(3) 0.031(3) 0.030(3) 0.000(2) -0.008(2) -0.008(2) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C00B O001 C008 124.2(4) . . ? C00D N003 C00F 121.6(4) . . ? C00D N003 C00M 121.7(4) . . ? C00M N003 C00F 115.9(4) . . ? C00K C005 C00E 121.3(4) . . ? C00L C005 C00E 120.3(4) . . ? C00L C005 C00K 118.4(4) . . ? H00A C006 H00B 109.5 . . ? H00A C006 H00C 109.5 . . ? H00B C006 H00C 109.5 . . ? C00F C006 H00A 109.5 . . ? C00F C006 H00B 109.5 . . ? C00F C006 H00C 109.5 . . ? C008 C007 C009 116.0(4) . . ? C008 C007 C00N 118.6(4) . . ? C009 C007 C00N 125.3(4) . . ? O001 C008 C007 118.8(4) . . ? C00H C008 O001 117.3(4) . . ? C00H C008 C007 123.9(4) . . ? C007 C009 H009 119.1 . . ? C00G C009 C007 121.8(4) . . ? C00G C009 H009 119.1 . . ? C00B C00A C00C 120.7(4) . . ? C00N C00A C00B 117.3(4) . . ? C00N C00A C00C 122.0(4) . . ? O001 C00B C00A 117.6(4) . . ? O002 C00B O001 115.2(4) . . ? O002 C00B C00A 127.2(4) . . ? C00I C00C C00A 122.7(4) . . ? C00J C00C C00A 120.6(4) . . ? C00J C00C C00I 116.8(4) . . ? N003 C00D C00G 121.6(4) . . ? N003 C00D C00H 122.0(4) . . ? C00H C00D C00G 116.4(4) . . ? N004 C00E C005 178.6(5) . . ? N003 C00F C006 112.6(4) . . ? N003 C00F H00D 109.1 . . ? N003 C00F H00E 109.1 . . ? C006 C00F H00D 109.1 . . ? C006 C00F H00E 109.1 . . ? H00D C00F H00E 107.8 . . ? C009 C00G C00D 121.9(4) . . ? C009 C00G H00G 119.0 . . ? C00D C00G H00G 119.0 . . ? C008 C00H C00D 120.0(4) . . ? C008 C00H H00H 120.0 . . ? C00D C00H H00H 120.0 . . ? C00C C00I H00I 119.5 . . ? C00L C00I C00C 121.0(5) . . ? C00L C00I H00I 119.5 . . ? C00C C00J H00J 118.7 . . ? C00K C00J C00C 122.6(4) . . ? C00K C00J H00J 118.7 . . ? C005 C00K H00K 120.2 . . ? C00J C00K C005 119.6(5) . . ? C00J C00K H00K 120.2 . . ? C005 C00L H00L 119.2 . . ? C00I C00L C005 121.6(4) . . ? C00I C00L H00L 119.2 . . ? N003 C00M H00F 108.9 . . ? N003 C00M H00M 108.9 . . ? N003 C00M C00O 113.3(4) . . ? H00F C00M H00M 107.7 . . ? C00O C00M H00F 108.9 . . ? C00O C00M H00M 108.9 . . ? C007 C00N H00N 118.4 . . ? C00A C00N C007 123.2(4) . . ? C00A C00N H00N 118.4 . . ? C00M C00O H00O 109.5 . . ? C00M C00O H00P 109.5 . . ? C00M C00O H00Q 109.5 . . ? H00O C00O H00P 109.5 . . ? H00O C00O H00Q 109.5 . . ? H00P C00O H00Q 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 1.376(5) . ? O001 C00B 1.374(6) . ? O002 C00B 1.209(6) . ? N003 C00D 1.351(6) . ? N003 C00F 1.467(6) . ? N003 C00M 1.467(6) . ? N004 C00E 1.148(6) . ? C005 C00E 1.438(7) . ? C005 C00K 1.400(7) . ? C005 C00L 1.392(7) . ? C006 H00A 0.9800 . ? C006 H00B 0.9800 . ? C006 H00C 0.9800 . ? C006 C00F 1.523(7) . ? C007 C008 1.401(7) . ? C007 C009 1.407(7) . ? C007 C00N 1.417(7) . ? C008 C00H 1.366(7) . ? C009 H009 0.9500 . ? C009 C00G 1.360(7) . ? C00A C00B 1.479(7) . ? C00A C00C 1.482(7) . ? C00A C00N 1.369(7) . ? C00C C00I 1.404(7) . ? C00C C00J 1.400(7) . ? C00D C00G 1.434(7) . ? C00D C00H 1.418(7) . ? C00F H00D 0.9900 . ? C00F H00E 0.9900 . ? C00G H00G 0.9500 . ? C00H H00H 0.9500 . ? C00I H00I 0.9500 . ? C00I C00L 1.375(7) . ? C00J H00J 0.9500 . ? C00J C00K 1.381(7) . ? C00K H00K 0.9500 . ? C00L H00L 0.9500 . ? C00M H00F 0.9900 . ? C00M H00M 0.9900 . ? C00M C00O 1.510(7) . ? C00N H00N 0.9500 . ? C00O H00O 0.9800 . ? C00O H00P 0.9800 . ? C00O H00Q 0.9800 . ? 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 O001 C008 C00H C00D -178.1(4) . . . . ? N003 C00D C00G C009 179.6(4) . . . . ? N003 C00D C00H C008 179.2(4) . . . . ? C007 C008 C00H C00D 1.8(7) . . . . ? C007 C009 C00G C00D 0.9(7) . . . . ? C008 O001 C00B O002 -174.6(4) . . . . ? C008 O001 C00B C00A 4.8(6) . . . . ? C008 C007 C009 C00G 0.2(7) . . . . ? C008 C007 C00N C00A 2.9(7) . . . . ? C009 C007 C008 O001 178.4(4) . . . . ? C009 C007 C008 C00H -1.5(7) . . . . ? C009 C007 C00N C00A -177.9(5) . . . . ? C00A C00C C00I C00L 180.0(4) . . . . ? C00A C00C C00J C00K 179.9(4) . . . . ? C00B O001 C008 C007 -1.6(7) . . . . ? C00B O001 C008 C00H 178.3(4) . . . . ? C00B C00A C00C C00I -9.3(7) . . . . ? C00B C00A C00C C00J 171.3(4) . . . . ? C00B C00A C00N C007 0.4(7) . . . . ? C00C C00A C00B O001 177.0(4) . . . . ? C00C C00A C00B O002 -3.7(8) . . . . ? C00C C00A C00N C007 179.3(4) . . . . ? C00C C00I C00L C005 0.1(8) . . . . ? C00C C00J C00K C005 0.2(8) . . . . ? C00D N003 C00F C006 79.3(6) . . . . ? C00D N003 C00M C00O 86.2(6) . . . . ? C00E C005 C00K C00J 180.0(5) . . . . ? C00E C005 C00L C00I 179.8(5) . . . . ? C00F N003 C00D C00G -176.6(4) . . . . ? C00F N003 C00D C00H 3.7(7) . . . . ? C00F N003 C00M C00O -103.7(5) . . . . ? C00G C00D C00H C008 -0.6(7) . . . . ? C00H C00D C00G C009 -0.7(7) . . . . ? C00I C00C C00J C00K 0.4(7) . . . . ? C00J C00C C00I C00L -0.5(7) . . . . ? C00K C005 C00L C00I 0.5(7) . . . . ? C00L C005 C00K C00J -0.7(7) . . . . ? C00M N003 C00D C00G -7.1(7) . . . . ? C00M N003 C00D C00H 173.1(4) . . . . ? C00M N003 C00F C006 -90.7(5) . . . . ? C00N C007 C008 O001 -2.4(7) . . . . ? C00N C007 C008 C00H 177.7(4) . . . . ? C00N C007 C009 C00G -179.0(5) . . . . ? C00N C00A C00B O001 -4.1(6) . . . . ? C00N C00A C00B O002 175.2(5) . . . . ? C00N C00A C00C C00I 171.9(5) . . . . ? C00N C00A C00C C00J -7.6(7) . . . . ? loop_ _twin_individual_id _twin_individual_mass_fraction_refined 1 0.851(7) 2 0.149(7)