#------------------------------------------------------------------------------ #$Date: 2020-07-06 04:54:12 +0300 (Mon, 06 Jul 2020) $ #$Revision: 253800 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/65/7126534.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_7126534 loop_ _publ_author_name 'He, Hui-Zi' 'Li, Kun' 'Yu, Kang-Kang' 'Lu, Pei-Long' 'Feng, Mei-Lin' 'Chen, Shan-Yong' 'Yu, Xiao-Qi' _publ_section_title ; Additive- and column-free synthesis of rigid bis-coumarins as fluorescent dyes for G-quadruplex sensing via disaggregation-induced emission. ; _journal_issue 50 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 6870 _journal_page_last 6873 _journal_paper_doi 10.1039/d0cc01437k _journal_volume 56 _journal_year 2020 _chemical_formula_moiety 'C27 H28 N2 O5' _chemical_formula_sum 'C27 H28 N2 O5' _chemical_formula_weight 460.51 _space_group_crystal_system monoclinic _space_group_IT_number 13 _space_group_name_Hall '-P 2yc' _space_group_name_H-M_alt 'P 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _audit_creation_date 2018-11-12 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-11-26 deposited with the CCDC. 2020-05-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 94.729(12) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 5.1905(5) _cell_length_b 9.3677(7) _cell_length_c 23.713(3) _cell_measurement_reflns_used 805 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.6480 _cell_measurement_theta_min 3.4580 _cell_volume 1149.1(2) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _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 ; Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008; Palatinus et al., 2012) ; _diffrn_ambient_temperature 293.15 _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.0874 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -42.00 0.00 0.6000 50.0000 omega____ theta____ kappa____ phi______ frames - -14.9669 19.0000 -60.0000 70 #__ type_ start__ end____ width___ exp.time_ 2 omega -20.20 56.00 0.6000 50.0000 omega____ theta____ kappa____ phi______ frames - 16.6856 -99.0000 -60.0000 127 #__ type_ start__ end____ width___ exp.time_ 3 omega -6.00 69.00 0.6000 50.0000 omega____ theta____ kappa____ phi______ frames - 16.6856 77.0000 90.0000 125 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0046933000 _diffrn_orient_matrix_UB_12 0.0665987000 _diffrn_orient_matrix_UB_13 -0.0142678000 _diffrn_orient_matrix_UB_21 -0.0013818000 _diffrn_orient_matrix_UB_22 0.0358526000 _diffrn_orient_matrix_UB_23 0.0263083000 _diffrn_orient_matrix_UB_31 0.1371061000 _diffrn_orient_matrix_UB_32 0.0026628000 _diffrn_orient_matrix_UB_33 0.0022758000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_unetI/netI 0.0459 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 2976 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.368 _diffrn_reflns_theta_min 3.379 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.41090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.25 _refine_diff_density_max 0.458 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.050 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 158 _refine_ls_number_reflns 2976 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.049 _refine_ls_R_factor_all 0.1006 _refine_ls_R_factor_gt 0.0630 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0662P)^2^+0.5474P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1520 _refine_ls_wR_factor_ref 0.1644 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1855 _reflns_number_total 2976 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0cc01437k2.cif _cod_data_source_block 181109_s2_hhz _cod_depositor_comments 'Adding full bibliography for 7126534.cif.' _cod_original_cell_volume 1149.0(2) _cod_database_code 7126534 _shelx_shelxl_version_number 2014/7 _chemical_oxdiff_formula c12h12n2o3 _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_estimated_absorpt_t_max 0.977 _shelx_estimated_absorpt_t_min 0.968 _reflns_odcompleteness_completeness 96.63 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Twinned data refinement Scales: 0.491(2) 0.509(2) 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. Others Fixed Sof: H10A(0.5) H10B(0.5) 4.a Secondary CH2 refined with riding coordinates: C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B) 4.b Aromatic/amide H refined with riding coordinates: C5(H5), C6(H6), C8(H8) 4.c Idealised Me refined as rotating group: C12(H12A,H12B,H12C), C14(H14A,H14B,H14C) ; _shelx_res_file ; 181109_s2_hhz.res created by SHELXL-2014/7 TITL CF solution in P2/c CELL 0.71073 5.19046 9.36767 23.71261 90 94.729 90 ZERR 2 0.0005 0.00073 0.00334 0 0.0118 0 LATT 1 SYMM -X,+Y,0.5-Z SFAC C H N O UNIT 54 56 4 10 L.S. 4 PLAN 25 SIZE 0.25 0.3 0.35 TEMP 20 fmap 2 acta bond $h htab conf SHEL 999 0.8 REM REM REM WGHT 0.066200 0.547400 BASF 0.50910 FVAR 6.07715 O1 4 0.011942 0.340981 0.352257 11.00000 0.05255 0.03053 = 0.05467 0.00570 0.02016 -0.00145 O2 4 0.137970 0.129921 0.325252 11.00000 0.07969 0.02773 = 0.10359 0.00671 0.04241 -0.00408 O3 4 0.500000 0.545593 0.250000 10.50000 0.04734 0.02681 = 0.04529 0.00000 0.02055 0.00000 N1 3 -0.324526 0.784136 0.410221 11.00000 0.07796 0.02508 = 0.07337 0.00420 0.04297 0.00388 C1 1 0.162162 0.257261 0.320199 11.00000 0.04139 0.03184 = 0.05885 0.00526 0.01038 -0.00131 C2 1 0.336202 0.325626 0.284481 11.00000 0.03725 0.02690 = 0.04834 0.00221 0.00387 -0.00138 C3 1 0.341665 0.469039 0.282959 11.00000 0.03110 0.02920 = 0.04112 0.00511 0.00552 -0.00318 C4 1 0.181367 0.557056 0.314353 11.00000 0.03409 0.02702 = 0.03455 0.00203 0.00557 -0.00276 C5 1 0.167805 0.706116 0.312874 11.00000 0.04720 0.03106 = 0.03717 0.00202 0.01121 -0.00518 AFIX 43 H5 2 0.274787 0.756019 0.290210 11.00000 -1.20000 AFIX 0 C6 1 0.003234 0.780067 0.343515 11.00000 0.04982 0.02984 = 0.04574 -0.00174 0.01353 0.00266 AFIX 43 H6 2 -0.002400 0.879096 0.340928 11.00000 -1.20000 AFIX 0 C7 1 -0.160608 0.708728 0.379484 11.00000 0.04136 0.04043 = 0.04118 0.00178 0.01296 0.00008 C8 1 -0.146885 0.560038 0.381392 11.00000 0.04421 0.03256 = 0.04641 0.00644 0.01254 -0.00696 AFIX 43 H8 2 -0.250341 0.509606 0.404663 11.00000 -1.20000 AFIX 0 C9 1 0.017543 0.487820 0.349304 11.00000 0.03922 0.02773 = 0.03940 0.00284 0.00019 -0.00106 C10 1 0.500000 0.232409 0.250000 10.50000 0.04963 0.02727 = 0.06249 0.00000 0.00913 0.00000 AFIX 23 H10A 2 0.609932 0.171748 0.274874 10.50000 -1.20000 H10B 2 0.390063 0.171753 0.225125 10.50000 -1.20000 AFIX 0 C11 1 -0.385253 0.940362 0.397207 11.00000 0.07784 0.09620 = 0.08759 -0.02269 0.04181 -0.01026 AFIX 23 H11A 2 -0.356883 0.960294 0.358057 11.00000 -1.20000 H11B 2 -0.565618 0.959053 0.402361 11.00000 -1.20000 AFIX 0 C12 1 -0.229339 1.029774 0.432598 11.00000 0.12257 0.13495 = 0.09038 -0.03529 0.05203 -0.04208 AFIX 137 H12A 2 -0.050787 1.009759 0.428115 11.00000 -1.50000 H12B 2 -0.264022 1.013516 0.471221 11.00000 -1.50000 H12C 2 -0.265988 1.127535 0.422795 11.00000 -1.50000 AFIX 0 C13 1 -0.473092 0.716234 0.452040 11.00000 0.05497 0.05009 = 0.05851 0.00066 0.02531 0.00029 AFIX 23 H13A 2 -0.550599 0.629735 0.435816 11.00000 -1.20000 H13B 2 -0.612321 0.779679 0.460604 11.00000 -1.20000 AFIX 0 C14 1 -0.317179 0.678881 0.506282 11.00000 0.09680 0.06901 = 0.05435 -0.00134 0.00814 -0.00723 AFIX 137 H14A 2 -0.183814 0.612399 0.498548 11.00000 -1.50000 H14B 2 -0.428030 0.636534 0.532110 11.00000 -1.50000 H14C 2 -0.240132 0.763856 0.522825 11.00000 -1.50000 AFIX 0 HKLF 5 REM CF solution in P2/c REM R1 = 0.0630 for 1855 Fo > 4sig(Fo) and 0.1006 for all 2976 data REM 158 parameters refined using 0 restraints END WGHT 0.0660 0.5475 REM Instructions for potential hydrogen bonds EQIV $1 x, y+1, z HTAB C6 O2_$1 REM Highest difference peak 0.458, deepest hole -0.252, 1-sigma level 0.050 Q1 1 -0.2097 0.9179 0.4302 11.00000 0.05 0.46 Q2 1 -0.4083 1.0523 0.3907 11.00000 0.05 0.36 Q3 1 0.0144 0.7373 0.3767 11.00000 0.05 0.18 Q4 1 0.1781 0.7618 0.3568 11.00000 0.05 0.18 Q5 1 0.4597 0.7544 0.2817 11.00000 0.05 0.18 Q6 1 0.4530 0.4055 0.3075 11.00000 0.05 0.17 Q7 1 0.3447 0.2770 0.2548 11.00000 0.05 0.17 Q8 1 0.3212 0.2771 0.3196 11.00000 0.05 0.16 Q9 1 -0.1719 0.5214 0.3376 11.00000 0.05 0.16 Q10 1 0.0023 0.7360 0.5099 11.00000 0.05 0.16 Q11 1 0.1797 0.5230 0.3482 11.00000 0.05 0.15 Q12 1 -0.1402 0.8389 0.4546 11.00000 0.05 0.15 Q13 1 0.1191 0.8413 0.4032 11.00000 0.05 0.15 Q14 1 0.3834 0.6891 0.2381 11.00000 0.05 0.15 Q15 1 -0.3008 0.9687 0.4728 11.00000 0.05 0.14 Q16 1 -0.1428 0.7667 0.4212 11.00000 0.05 0.14 Q17 1 0.2270 0.4032 0.2629 11.00000 0.05 0.14 Q18 1 -0.0066 0.5278 0.3126 11.00000 0.05 0.14 Q19 1 0.3219 0.5145 0.3177 11.00000 0.05 0.14 Q20 1 -0.4060 1.1488 0.4623 11.00000 0.05 0.14 Q21 1 -0.5379 0.9550 0.4786 11.00000 0.05 0.14 Q22 1 -0.6399 0.7575 0.5198 11.00000 0.05 0.14 Q23 1 -0.4966 1.1247 0.3486 11.00000 0.05 0.14 Q24 1 -0.2748 0.6806 0.5795 11.00000 0.05 0.14 Q25 1 -0.7330 0.6248 0.4537 11.00000 0.05 0.14 ; _shelx_res_checksum 43903 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' 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 0.0119(4) 0.3410(2) 0.35226(10) 0.0450(7) Uani 1 1 d . . . . . O2 O 0.1380(5) 0.1299(2) 0.32525(13) 0.0684(9) Uani 1 1 d . . . . . O3 O 0.5000 0.5456(3) 0.2500 0.0389(9) Uani 1 2 d S T P . . N1 N -0.3245(6) 0.7841(3) 0.41022(14) 0.0568(10) Uani 1 1 d . . . . . C1 C 0.1622(7) 0.2573(4) 0.32020(17) 0.0437(9) Uani 1 1 d . . . . . C2 C 0.3362(6) 0.3256(3) 0.28448(15) 0.0375(8) Uani 1 1 d . . . . . C3 C 0.3417(6) 0.4690(3) 0.28296(15) 0.0337(8) Uani 1 1 d . . . . . C4 C 0.1814(6) 0.5571(3) 0.31435(14) 0.0317(8) Uani 1 1 d . . . . . C5 C 0.1678(7) 0.7061(3) 0.31287(14) 0.0380(9) Uani 1 1 d . . . . . H5 H 0.2748 0.7560 0.2902 0.046 Uiso 1 1 calc R . . . . C6 C 0.0032(6) 0.7801(3) 0.34352(15) 0.0413(10) Uani 1 1 d . . . . . H6 H -0.0024 0.8791 0.3409 0.050 Uiso 1 1 calc R . . . . C7 C -0.1606(7) 0.7087(4) 0.37948(16) 0.0405(9) Uani 1 1 d . . . . . C8 C -0.1469(6) 0.5600(3) 0.38139(15) 0.0406(9) Uani 1 1 d . . . . . H8 H -0.2503 0.5096 0.4047 0.049 Uiso 1 1 calc R . . . . C9 C 0.0175(6) 0.4878(3) 0.34930(14) 0.0356(9) Uani 1 1 d . . . . . C10 C 0.5000 0.2324(5) 0.2500 0.0462(14) Uani 1 2 d S T P . . H10A H 0.6099 0.1717 0.2749 0.055 Uiso 0.5 1 calc R . . . . H10B H 0.3901 0.1718 0.2251 0.055 Uiso 0.5 1 calc R . . . . C11 C -0.3853(9) 0.9404(5) 0.3972(2) 0.0853(16) Uani 1 1 d . . . . . H11A H -0.3569 0.9603 0.3581 0.102 Uiso 1 1 calc R . . . . H11B H -0.5656 0.9591 0.4024 0.102 Uiso 1 1 calc R . . . . C12 C -0.2293(11) 1.0298(6) 0.4326(2) 0.114(2) Uani 1 1 d . . . . . H12A H -0.0508 1.0098 0.4281 0.170 Uiso 1 1 calc GR . . . . H12B H -0.2640 1.0135 0.4712 0.170 Uiso 1 1 calc GR . . . . H12C H -0.2660 1.1275 0.4228 0.170 Uiso 1 1 calc GR . . . . C13 C -0.4731(7) 0.7162(4) 0.45204(17) 0.0534(11) Uani 1 1 d . . . . . H13A H -0.5506 0.6297 0.4358 0.064 Uiso 1 1 calc R . . . . H13B H -0.6123 0.7797 0.4606 0.064 Uiso 1 1 calc R . . . . C14 C -0.3172(9) 0.6789(4) 0.50628(18) 0.0733(14) Uani 1 1 d . . . . . H14A H -0.1838 0.6124 0.4985 0.110 Uiso 1 1 calc GR . . . . H14B H -0.4280 0.6365 0.5321 0.110 Uiso 1 1 calc GR . . . . H14C H -0.2401 0.7639 0.5228 0.110 Uiso 1 1 calc GR . . . . 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 0.0525(17) 0.0305(14) 0.0547(17) 0.0057(12) 0.0202(14) -0.0014(11) O2 0.080(2) 0.0277(15) 0.104(3) 0.0067(15) 0.0424(18) -0.0041(13) O3 0.047(2) 0.0268(18) 0.045(2) 0.000 0.0205(19) 0.000 N1 0.078(2) 0.0251(16) 0.073(3) 0.0042(16) 0.043(2) 0.0039(16) C1 0.041(2) 0.032(2) 0.059(3) 0.0053(19) 0.010(2) -0.0013(17) C2 0.037(2) 0.0269(18) 0.048(2) 0.0022(17) 0.0039(18) -0.0014(16) C3 0.0311(19) 0.0292(18) 0.041(2) 0.0051(17) 0.0055(17) -0.0032(16) C4 0.0341(19) 0.0270(17) 0.035(2) 0.0020(15) 0.0056(17) -0.0028(16) C5 0.047(2) 0.0311(18) 0.037(2) 0.0020(16) 0.0112(19) -0.0052(17) C6 0.050(2) 0.0298(19) 0.046(2) -0.0017(17) 0.014(2) 0.0027(17) C7 0.041(2) 0.040(2) 0.041(2) 0.0018(17) 0.0130(18) 0.0001(18) C8 0.044(2) 0.033(2) 0.046(2) 0.0064(17) 0.013(2) -0.0070(17) C9 0.039(2) 0.0277(19) 0.039(2) 0.0028(16) 0.0002(19) -0.0011(16) C10 0.050(3) 0.027(3) 0.062(4) 0.000 0.009(3) 0.000 C11 0.078(4) 0.096(4) 0.088(4) -0.023(3) 0.042(3) -0.010(3) C12 0.123(5) 0.135(5) 0.090(4) -0.035(4) 0.052(4) -0.042(4) C13 0.055(3) 0.050(2) 0.059(3) 0.001(2) 0.025(2) 0.000(2) C14 0.097(4) 0.069(3) 0.054(3) -0.001(2) 0.008(3) -0.007(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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 C9 O1 C1 121.7(3) . . ? C3 O3 C3 117.4(3) 2_655 . ? C7 N1 C11 121.2(3) . . ? C7 N1 C13 121.9(3) . . ? C13 N1 C11 116.5(3) . . ? O1 C1 C2 118.9(3) . . ? O2 C1 O1 116.1(3) . . ? O2 C1 C2 125.0(3) . . ? C1 C2 C10 118.1(3) . . ? C3 C2 C1 118.4(3) . . ? C3 C2 C10 123.4(3) . . ? O3 C3 C4 113.3(3) . . ? C2 C3 O3 123.3(3) . . ? C2 C3 C4 123.4(3) . . ? C5 C4 C3 126.5(3) . . ? C9 C4 C3 116.9(3) . . ? C9 C4 C5 116.6(3) . . ? C4 C5 H5 119.0 . . ? C6 C5 C4 121.9(3) . . ? C6 C5 H5 119.0 . . ? C5 C6 H6 119.5 . . ? C5 C6 C7 121.1(3) . . ? C7 C6 H6 119.5 . . ? N1 C7 C6 120.6(3) . . ? N1 C7 C8 122.2(3) . . ? C8 C7 C6 117.2(3) . . ? C7 C8 H8 119.7 . . ? C9 C8 C7 120.5(3) . . ? C9 C8 H8 119.7 . . ? O1 C9 C4 120.7(3) . . ? C8 C9 O1 116.7(3) . . ? C8 C9 C4 122.6(3) . . ? C2 C10 C2 109.1(4) 2_655 . ? C2 C10 H10A 109.9 . . ? C2 C10 H10A 109.9 2_655 . ? C2 C10 H10B 109.9 2_655 . ? C2 C10 H10B 109.9 . . ? H10A C10 H10B 108.3 . . ? N1 C11 H11A 109.5 . . ? N1 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C12 C11 N1 110.8(5) . . ? C12 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N1 C13 H13A 108.7 . . ? N1 C13 H13B 108.7 . . ? N1 C13 C14 114.0(3) . . ? H13A C13 H13B 107.6 . . ? C14 C13 H13A 108.7 . . ? C14 C13 H13B 108.7 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 O1 C1 1.378(4) . ? O1 C9 1.378(3) . ? O2 C1 1.206(4) . ? O3 C3 1.381(3) . ? O3 C3 1.381(3) 2_655 ? N1 C7 1.362(4) . ? N1 C11 1.523(5) . ? N1 C13 1.452(4) . ? C1 C2 1.439(5) . ? C2 C3 1.344(4) . ? C2 C10 1.506(4) . ? C3 C4 1.424(4) . ? C4 C5 1.398(4) . ? C4 C9 1.395(4) . ? C5 H5 0.9300 . ? C5 C6 1.356(4) . ? C6 H6 0.9300 . ? C6 C7 1.420(4) . ? C7 C8 1.395(4) . ? C8 H8 0.9300 . ? C8 C9 1.368(4) . ? C10 C2 1.506(4) 2_655 ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 C12 1.396(6) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C13 C14 1.503(5) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 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 O1 C1 C2 C3 -1.3(5) . . . . ? O1 C1 C2 C10 179.7(3) . . . . ? O2 C1 C2 C3 179.8(4) . . . . ? O2 C1 C2 C10 0.7(6) . . . . ? O3 C3 C4 C5 2.1(5) . . . . ? O3 C3 C4 C9 -179.3(3) . . . . ? N1 C7 C8 C9 179.1(4) . . . . ? C1 O1 C9 C4 -1.4(5) . . . . ? C1 O1 C9 C8 177.6(3) . . . . ? C1 C2 C3 O3 -179.7(3) . . . . ? C1 C2 C3 C4 -0.9(6) . . . . ? C1 C2 C10 C2 179.3(4) . . . 2_655 ? C2 C3 C4 C5 -176.8(4) . . . . ? C2 C3 C4 C9 1.8(5) . . . . ? C3 O3 C3 C2 0.3(3) 2_655 . . . ? C3 O3 C3 C4 -178.6(3) 2_655 . . . ? C3 C2 C10 C2 0.3(3) . . . 2_655 ? C3 C4 C5 C6 178.3(4) . . . . ? C3 C4 C9 O1 -0.7(5) . . . . ? C3 C4 C9 C8 -179.6(3) . . . . ? C4 C5 C6 C7 1.1(6) . . . . ? C5 C4 C9 O1 178.1(3) . . . . ? C5 C4 C9 C8 -0.8(5) . . . . ? C5 C6 C7 N1 179.8(4) . . . . ? C5 C6 C7 C8 -0.7(5) . . . . ? C6 C7 C8 C9 -0.5(5) . . . . ? C7 N1 C11 C12 -96.6(5) . . . . ? C7 N1 C13 C14 75.5(5) . . . . ? C7 C8 C9 O1 -177.8(3) . . . . ? C7 C8 C9 C4 1.2(5) . . . . ? C9 O1 C1 O2 -178.5(3) . . . . ? C9 O1 C1 C2 2.5(5) . . . . ? C9 C4 C5 C6 -0.3(5) . . . . ? C10 C2 C3 O3 -0.6(5) . . . . ? C10 C2 C3 C4 178.1(3) . . . . ? C11 N1 C7 C6 14.6(6) . . . . ? C11 N1 C7 C8 -164.9(4) . . . . ? C11 N1 C13 C14 -111.8(4) . . . . ? C13 N1 C7 C6 -173.0(4) . . . . ? C13 N1 C7 C8 7.5(6) . . . . ? C13 N1 C11 C12 90.6(5) . . . . ? loop_ _twin_individual_id _twin_individual_mass_fraction_refined 1 0.491(2) 2 0.509(2)