#------------------------------------------------------------------------------ #$Date: 2020-05-07 21:40:48 +0300 (Thu, 07 May 2020) $ #$Revision: 251876 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240479.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_7240479 loop_ _publ_author_name 'Colin-Molina, Abraham' 'Velazquez-Chavez, Diego' 'Jellen, Marcus' 'Rodr\'iguez-Cort\'es, Lizbeth A.' 'Cifuentes Quintal, Miguel Eduardo' 'Merino, Gabriel' 'Rodr\'iguez-Molina, Braulio' _publ_section_title ; Dynamic Characterization of Crystalline Fluorophores with Conformationally Flexible Tetrahydrocarbazole Frameworks ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D0CE00423E _journal_year 2020 _chemical_formula_moiety 'C30 H28 N2' _chemical_formula_sum 'C30 H28 N2' _chemical_formula_weight 416.54 _chemical_melting_point 574 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2020-04-22 deposited with the CCDC. 2020-05-06 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.76(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 11.609(12) _cell_length_b 7.722(7) _cell_length_c 12.775(13) _cell_measurement_reflns_used 2053 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 27.46 _cell_measurement_theta_min 2.35 _cell_volume 1145(2) _computing_cell_refinement 'APEX2 v2014.1-1(Bruker, 2014)' _computing_data_collection 'APEX2 v2014.1-1(Bruker, 2014)' _computing_data_reduction 'SAINT V8.34A (Bruker, 2014)' _computing_molecular_graphics 'SHELXLe (H?bschle et al, 2011)' _computing_publication_material 'CIFTAB V 2013/2 (Sheldrick, 2013)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXS-2012 (Bruker, 2013)' _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 52.0833 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Bruker D8 Venture \k geometry diffractometer 208039-1' _diffrn_measurement_method '\f and \w-scans' _diffrn_radiation_monochromator 'Helios multilayer mirror' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1722 _diffrn_reflns_av_unetI/netI 0.1629 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 10668 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.672 _diffrn_reflns_theta_min 2.355 _diffrn_source 'micro-focus X-ray source' _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.4136 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Sheldrick, 2012)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.208 _exptl_crystal_description prism _exptl_crystal_F_000 444 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF' _exptl_crystal_size_max 0.382 _exptl_crystal_size_mid 0.369 _exptl_crystal_size_min 0.290 _refine_diff_density_max 0.148 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.045 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 183 _refine_ls_number_reflns 2162 _refine_ls_number_restraints 66 _refine_ls_restrained_S_all 0.998 _refine_ls_R_factor_all 0.2727 _refine_ls_R_factor_gt 0.0956 _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^)+(0.1306P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2145 _refine_ls_wR_factor_ref 0.2974 _reflns_Friedel_coverage 0.000 _reflns_number_gt 725 _reflns_number_total 2162 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00423e2.cif _cod_data_source_block Compound_2 _cod_original_cell_volume 1145.1(19) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7240479 _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. ; _shelx_estimated_absorpt_t_min 0.974 _shelx_estimated_absorpt_t_max 0.980 _shelx_res_file ; TITL Compound_2 Compound_2.res created by SHELXL-2018/3 at 13:58:28 on 15-Apr-2020 CELL 0.71073 11.60860 7.72240 12.77490 90.0000 90.7560 90.0000 ZERR 2.00 0.01150 0.00730 0.01280 0.0000 0.0273 0.0000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H N UNIT 60 56 4 OMIT 13 0 5 OMIT -10 0 4 OMIT 5 3 5 OMIT 9 3 1 OMIT 2 8 1 OMIT 3 3 0 OMIT -7 4 5 OMIT -6 3 3 OMIT -7 0 11 OMIT -9 6 3 OMIT -2 4 12 OMIT 11 3 5 LIST 4 L.S. 20 TEMP 25.00 SIZE 0.290 0.369 0.382 ACTA CONF BOND $H HTAB FMAP 2 PLAN 5 WGHT 0.130600 FVAR 0.19741 0.67757 0.55563 C1 1 0.613739 0.326910 0.274689 11.00000 0.10048 0.09299 = 0.09798 0.00232 -0.00481 -0.01160 AFIX 23 H1A 2 0.604532 0.219673 0.235937 11.00000 -1.20000 H1B 2 0.662559 0.302456 0.335101 11.00000 -1.20000 AFIX 0 SADI 0.01 C1 C2 C1 C2B C4 C3 C4 C3B SIMU 0.01 C2 > C3B DELU 0.005 C2 > C3B PART 1 C2 1 0.674670 0.454044 0.206720 21.00000 0.11226 0.10810 = 0.12694 0.00003 0.02454 -0.03979 AFIX 23 H2A 2 0.731768 0.394488 0.165242 21.00000 -1.20000 H2B 2 0.714049 0.539286 0.249970 21.00000 -1.20000 AFIX 0 C3 1 0.589205 0.542493 0.135879 21.00000 0.12233 0.11637 = 0.12052 0.01431 0.00841 -0.06178 AFIX 23 H3A 2 0.563038 0.458787 0.084187 21.00000 -1.20000 H3B 2 0.629439 0.633133 0.098587 21.00000 -1.20000 AFIX 0 PART 2 SAME 0.01 0.01 C2 C3 C2B 1 0.626989 0.428482 0.174545 -21.00000 0.10515 0.11304 = 0.12632 0.00153 0.01942 -0.04637 AFIX 23 H2C 2 0.703344 0.405965 0.147770 -21.00000 -1.20000 H2D 2 0.571923 0.383658 0.123608 -21.00000 -1.20000 AFIX 0 C3B 1 0.611121 0.621782 0.180818 -21.00000 0.11534 0.11229 = 0.13100 0.01447 0.01162 -0.05752 AFIX 23 H3C 2 0.646576 0.670678 0.243323 -21.00000 -1.20000 H3D 2 0.639521 0.680714 0.119269 -21.00000 -1.20000 AFIX 0 PART C4 1 0.483021 0.623030 0.185338 11.00000 0.18306 0.08796 = 0.09724 0.01847 -0.01648 -0.02838 AFIX 23 H4A 2 0.502206 0.737769 0.211079 11.00000 -1.20000 H4B 2 0.422821 0.635170 0.132468 11.00000 -1.20000 AFIX 0 C5 1 0.242721 0.644641 0.329423 11.00000 0.13440 0.06607 = 0.10346 -0.00897 -0.03819 0.02628 AFIX 43 H5 2 0.237120 0.732539 0.279853 11.00000 -1.20000 AFIX 0 C6 1 0.158809 0.621098 0.403791 11.00000 0.13761 0.11803 = 0.14725 -0.01239 -0.02798 0.07078 AFIX 43 H6 2 0.095395 0.694701 0.403313 11.00000 -1.20000 AFIX 0 C7 1 0.165290 0.494403 0.477744 11.00000 0.08386 0.11719 = 0.14338 -0.00813 -0.00611 0.04020 AFIX 43 H7 2 0.107037 0.486580 0.526802 11.00000 -1.20000 AFIX 0 C8 1 0.254753 0.377316 0.482772 11.00000 0.07233 0.09241 = 0.09714 -0.00268 0.00313 0.01469 AFIX 43 H8 2 0.258071 0.289878 0.532781 11.00000 -1.20000 AFIX 0 N9 3 0.441746 0.305034 0.393980 11.00000 0.06745 0.05302 = 0.08197 0.00577 -0.00033 0.00438 C10 1 0.500235 0.380643 0.312043 11.00000 0.07152 0.06516 = 0.09147 0.00221 -0.00072 -0.00206 C11 1 0.439656 0.516848 0.272678 11.00000 0.10644 0.05527 = 0.08479 0.00128 -0.01862 -0.00837 C12 1 0.336982 0.530159 0.331785 11.00000 0.09664 0.05098 = 0.08846 -0.00776 -0.02637 0.00905 C13 1 0.340713 0.398713 0.407320 11.00000 0.07656 0.05403 = 0.07949 -0.00892 -0.01528 0.01046 C14 1 0.471549 0.150750 0.447989 11.00000 0.06668 0.04240 = 0.07085 0.00520 -0.00405 0.00571 SIMU 0.01 C15 > C16B DELU 0.005 C15 > C16B PART 1 C15 1 0.572632 0.140476 0.503609 31.00000 0.06518 0.05006 = 0.08541 0.00174 -0.01176 -0.00597 AFIX 43 H15 2 0.621495 0.235796 0.507090 31.00000 -1.20000 AFIX 0 C16 1 0.601971 -0.008048 0.553720 31.00000 0.06537 0.05582 = 0.09047 0.00466 -0.01091 0.00103 AFIX 43 H16 2 0.671999 -0.014867 0.589689 31.00000 -1.20000 AFIX 0 PART 2 SAME 0.01 C15 C16 C15B 1 0.488549 -0.002195 0.395377 -31.00000 0.08114 0.06462 = 0.06092 0.00885 -0.00588 -0.00104 AFIX 43 H15B 2 0.481471 -0.005018 0.322798 -31.00000 -1.20000 AFIX 0 C16B 1 0.515616 -0.149269 0.448613 -31.00000 0.06909 0.05453 = 0.07013 -0.00102 -0.00877 0.00377 AFIX 43 H16B 2 0.525427 -0.251778 0.411577 -31.00000 -1.20000 PART 0 AFIX 0 HKLF 4 REM Compound_2 REM wR2 = 0.2974, GooF = S = 0.996, Restrained GooF = 0.998 for all data REM R1 = 0.0956 for 725 Fo > 4sig(Fo) and 0.2727 for all 2162 data REM 183 parameters refined using 66 restraints END WGHT 0.1306 0.0000 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.148, deepest hole -0.199, 1-sigma level 0.045 Q1 1 0.2536 0.6932 0.4782 11.00000 0.05 0.15 Q2 1 0.6480 0.2076 0.3167 11.00000 0.05 0.15 Q3 1 0.1379 0.5926 0.4184 11.00000 0.05 0.13 Q4 1 0.5235 -0.2876 0.4807 11.00000 0.05 0.13 Q5 1 0.4373 0.1512 0.3628 11.00000 0.05 0.13 ; _shelx_res_checksum 55709 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, 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 C1 C 0.6137(5) 0.3269(7) 0.2747(4) 0.0972(18) Uani 1 1 d D . . . . H1A H 0.604532 0.219673 0.235937 0.117 Uiso 1 1 calc R U . A 1 H1B H 0.662559 0.302456 0.335101 0.117 Uiso 1 1 calc R U . A 1 C2 C 0.6747(8) 0.4540(14) 0.2067(10) 0.116(3) Uani 0.678(13) 1 d D U P B 1 H2A H 0.731768 0.394488 0.165242 0.139 Uiso 0.678(13) 1 calc R U P B 1 H2B H 0.714049 0.539286 0.249970 0.139 Uiso 0.678(13) 1 calc R U P B 1 C3 C 0.5892(8) 0.5425(16) 0.1359(8) 0.120(3) Uani 0.678(13) 1 d D U P B 1 H3A H 0.563038 0.458787 0.084187 0.144 Uiso 0.678(13) 1 calc R U P B 1 H3B H 0.629439 0.633133 0.098587 0.144 Uiso 0.678(13) 1 calc R U P B 1 C2B C 0.627(3) 0.428(2) 0.1745(11) 0.115(4) Uani 0.322(13) 1 d D U P B 2 H2C H 0.703344 0.405965 0.147770 0.138 Uiso 0.322(13) 1 calc R U P B 2 H2D H 0.571923 0.383658 0.123608 0.138 Uiso 0.322(13) 1 calc R U P B 2 C3B C 0.6111(9) 0.622(2) 0.181(2) 0.119(4) Uani 0.322(13) 1 d D U P B 2 H3C H 0.646576 0.670678 0.243323 0.143 Uiso 0.322(13) 1 calc R U P B 2 H3D H 0.639521 0.680714 0.119269 0.143 Uiso 0.322(13) 1 calc R U P B 2 C4 C 0.4830(7) 0.6230(8) 0.1853(5) 0.123(2) Uani 1 1 d D . . . . H4A H 0.502206 0.737769 0.211079 0.147 Uiso 1 1 calc R U . B 1 H4B H 0.422821 0.635170 0.132468 0.147 Uiso 1 1 calc R U . B 1 C5 C 0.2427(6) 0.6446(7) 0.3294(5) 0.102(2) Uani 1 1 d . . . . . H5 H 0.237120 0.732539 0.279853 0.122 Uiso 1 1 calc R U . . . C6 C 0.1588(7) 0.6211(11) 0.4038(6) 0.135(3) Uani 1 1 d . . . . . H6 H 0.095395 0.694701 0.403313 0.161 Uiso 1 1 calc R U . . . C7 C 0.1653(5) 0.4944(9) 0.4777(6) 0.115(2) Uani 1 1 d . . . . . H7 H 0.107037 0.486580 0.526802 0.138 Uiso 1 1 calc R U . . . C8 C 0.2548(5) 0.3773(7) 0.4828(4) 0.0873(17) Uani 1 1 d . . . . . H8 H 0.258071 0.289878 0.532781 0.105 Uiso 1 1 calc R U . . . N9 N 0.4417(3) 0.3050(5) 0.3940(3) 0.0675(12) Uani 1 1 d . . . . . C10 C 0.5002(4) 0.3806(7) 0.3120(4) 0.0761(15) Uani 1 1 d . . . . . C11 C 0.4397(6) 0.5168(7) 0.2727(4) 0.0823(16) Uani 1 1 d . . . . . C12 C 0.3370(5) 0.5302(6) 0.3318(5) 0.0789(16) Uani 1 1 d . . . . . C13 C 0.3407(4) 0.3987(6) 0.4073(4) 0.0702(14) Uani 1 1 d . . . . . C14 C 0.4715(4) 0.1508(6) 0.4480(4) 0.0600(13) Uani 1 1 d . . . . . C15 C 0.5726(8) 0.1405(10) 0.5036(7) 0.067(3) Uani 0.556(8) 1 d D U P C 1 H15 H 0.621495 0.235796 0.507090 0.080 Uiso 0.556(8) 1 calc R U P C 1 C16 C 0.6020(9) -0.0080(10) 0.5537(7) 0.071(3) Uani 0.556(8) 1 d D U P C 1 H16 H 0.671999 -0.014867 0.589689 0.085 Uiso 0.556(8) 1 calc R U P C 1 C15B C 0.4885(10) -0.0022(13) 0.3954(9) 0.069(3) Uani 0.444(8) 1 d D U P C 2 H15B H 0.481471 -0.005018 0.322798 0.083 Uiso 0.444(8) 1 calc R U P C 2 C16B C 0.5156(10) -0.1493(12) 0.4486(9) 0.065(3) Uani 0.444(8) 1 d D U P C 2 H16B H 0.525427 -0.251778 0.411577 0.078 Uiso 0.444(8) 1 calc R U P C 2 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 C1 0.100(5) 0.093(4) 0.098(4) 0.002(3) -0.005(4) -0.012(4) C2 0.112(7) 0.108(7) 0.127(7) 0.000(6) 0.025(5) -0.040(5) C3 0.122(7) 0.116(8) 0.121(8) 0.014(6) 0.008(5) -0.062(6) C2B 0.105(8) 0.113(8) 0.126(9) 0.002(7) 0.019(7) -0.046(7) C3B 0.115(8) 0.112(8) 0.131(9) 0.014(7) 0.012(7) -0.058(7) C4 0.183(7) 0.088(4) 0.097(5) 0.018(4) -0.016(5) -0.028(5) C5 0.134(6) 0.066(4) 0.103(5) -0.009(4) -0.038(4) 0.026(4) C6 0.138(7) 0.118(6) 0.147(7) -0.012(5) -0.028(6) 0.071(5) C7 0.084(4) 0.117(5) 0.143(6) -0.008(5) -0.006(4) 0.040(4) C8 0.072(4) 0.092(4) 0.097(4) -0.003(3) 0.003(3) 0.015(3) N9 0.067(3) 0.053(2) 0.082(3) 0.006(2) 0.000(2) 0.004(2) C10 0.072(4) 0.065(4) 0.091(4) 0.002(3) -0.001(3) -0.002(3) C11 0.106(5) 0.055(3) 0.085(4) 0.001(3) -0.019(4) -0.008(3) C12 0.097(5) 0.051(3) 0.088(4) -0.008(3) -0.026(4) 0.009(3) C13 0.077(4) 0.054(3) 0.079(4) -0.009(3) -0.015(3) 0.010(3) C14 0.067(3) 0.042(3) 0.071(4) 0.005(3) -0.004(3) 0.006(2) C15 0.065(6) 0.050(4) 0.085(6) 0.002(4) -0.012(5) -0.006(4) C16 0.065(5) 0.056(4) 0.090(6) 0.005(4) -0.011(5) 0.001(5) C15B 0.081(8) 0.065(6) 0.061(6) 0.009(5) -0.006(6) -0.001(6) C16B 0.069(6) 0.055(5) 0.070(7) -0.001(4) -0.009(5) 0.004(5) 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' 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 C10 C1 C2 115.9(6) . . ? C10 C1 C2B 103.3(13) . . ? C10 C1 H1A 108.3 . . ? C2 C1 H1A 108.3 . . ? C10 C1 H1B 108.3 . . ? C2 C1 H1B 108.3 . . ? H1A C1 H1B 107.4 . . ? C1 C2 C3 109.6(8) . . ? C1 C2 H2A 109.7 . . ? C3 C2 H2A 109.7 . . ? C1 C2 H2B 109.7 . . ? C3 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C2 C3 C4 117.9(9) . . ? C2 C3 H3A 107.8 . . ? C4 C3 H3A 107.8 . . ? C2 C3 H3B 107.8 . . ? C4 C3 H3B 107.8 . . ? H3A C3 H3B 107.2 . . ? C3B C2B C1 117.1(16) . . ? C3B C2B H2C 108.0 . . ? C1 C2B H2C 108.0 . . ? C3B C2B H2D 108.0 . . ? C1 C2B H2D 108.0 . . ? H2C C2B H2D 107.3 . . ? C4 C3B C2B 97.5(17) . . ? C4 C3B H3C 112.3 . . ? C2B C3B H3C 112.3 . . ? C4 C3B H3D 112.3 . . ? C2B C3B H3D 112.3 . . ? H3C C3B H3D 109.9 . . ? C11 C4 C3B 112.1(10) . . ? C11 C4 C3 111.8(7) . . ? C11 C4 H4A 109.3 . . ? C3 C4 H4A 109.3 . . ? C11 C4 H4B 109.3 . . ? C3 C4 H4B 109.3 . . ? H4A C4 H4B 107.9 . . ? C6 C5 C12 117.2(6) . . ? C6 C5 H5 121.4 . . ? C12 C5 H5 121.4 . . ? C7 C6 C5 122.6(7) . . ? C7 C6 H6 118.7 . . ? C5 C6 H6 118.7 . . ? C6 C7 C8 122.6(7) . . ? C6 C7 H7 118.7 . . ? C8 C7 H7 118.7 . . ? C7 C8 C13 115.6(5) . . ? C7 C8 H8 122.2 . . ? C13 C8 H8 122.2 . . ? C10 N9 C13 107.2(4) . . ? C10 N9 C14 127.1(4) . . ? C13 N9 C14 125.4(4) . . ? C11 C10 N9 110.5(5) . . ? C11 C10 C1 124.2(6) . . ? N9 C10 C1 125.3(5) . . ? C10 C11 C12 107.0(5) . . ? C10 C11 C4 122.0(6) . . ? C12 C11 C4 131.0(6) . . ? C13 C12 C5 119.2(6) . . ? C13 C12 C11 107.1(5) . . ? C5 C12 C11 133.7(6) . . ? N9 C13 C12 108.1(5) . . ? N9 C13 C8 129.1(5) . . ? C12 C13 C8 122.8(5) . . ? C16B C14 C15B 117.7(6) 3_656 . ? C15 C14 C16 118.9(5) . 3_656 ? C16B C14 N9 121.0(6) 3_656 . ? C15 C14 N9 120.3(5) . . ? C15B C14 N9 121.3(6) . . ? C16 C14 N9 120.8(5) 3_656 . ? C16 C15 C14 120.3(7) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C14 120.8(7) . 3_656 ? C15 C16 H16 119.6 . . ? C14 C16 H16 119.6 3_656 . ? C16B C15B C14 120.5(9) . . ? C16B C15B H15B 119.8 . . ? C14 C15B H15B 119.8 . . ? C14 C16B C15B 121.8(10) 3_656 . ? C14 C16B H16B 119.1 3_656 . ? C15B C16B H16B 119.1 . . ? 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 C1 C10 1.467(6) . ? C1 C2 1.495(7) . ? C1 C2B 1.510(9) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.499(12) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.525(8) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C2B C3B 1.506(14) . ? C2B H2C 0.9700 . ? C2B H2D 0.9700 . ? C3B C4 1.489(9) . ? C3B H3C 0.9700 . ? C3B H3D 0.9700 . ? C4 C11 1.478(7) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.382(8) . ? C5 C12 1.407(7) . ? C5 H5 0.9300 . ? C6 C7 1.361(9) . ? C6 H6 0.9300 . ? C7 C8 1.378(7) . ? C7 H7 0.9300 . ? C8 C13 1.406(6) . ? C8 H8 0.9300 . ? N9 C10 1.384(6) . ? N9 C13 1.390(6) . ? N9 C14 1.417(5) . ? C10 C11 1.358(6) . ? C11 C12 1.423(8) . ? C12 C13 1.401(6) . ? C14 C16B 1.327(11) 3_656 ? C14 C15 1.366(9) . ? C14 C15B 1.374(11) . ? C14 C16 1.394(9) 3_656 ? C15 C16 1.355(8) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C15B C16B 1.359(9) . ? C15B H15B 0.9300 . ? C16B H16B 0.9300 . ? 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 C10 C1 C2 C3 -37.8(14) . . . . ? C1 C2 C3 C4 51.3(18) . . . . ? C10 C1 C2B C3B 54(2) . . . . ? C1 C2B C3B C4 -77(3) . . . . ? C2B C3B C4 C11 55.8(17) . . . . ? C2 C3 C4 C11 -37.3(14) . . . . ? C12 C5 C6 C7 0.5(10) . . . . ? C5 C6 C7 C8 -1.5(11) . . . . ? C6 C7 C8 C13 1.1(8) . . . . ? C13 N9 C10 C11 -0.6(5) . . . . ? C14 N9 C10 C11 173.4(4) . . . . ? C13 N9 C10 C1 177.2(4) . . . . ? C14 N9 C10 C1 -8.8(8) . . . . ? C2 C1 C10 C11 13.9(9) . . . . ? C2B C1 C10 C11 -12.1(10) . . . . ? C2 C1 C10 N9 -163.6(7) . . . . ? C2B C1 C10 N9 170.4(9) . . . . ? N9 C10 C11 C12 -0.1(6) . . . . ? C1 C10 C11 C12 -177.9(5) . . . . ? N9 C10 C11 C4 179.1(4) . . . . ? C1 C10 C11 C4 1.2(8) . . . . ? C3B C4 C11 C10 -26.8(12) . . . . ? C3 C4 C11 C10 9.7(9) . . . . ? C3B C4 C11 C12 152.2(12) . . . . ? C3 C4 C11 C12 -171.4(7) . . . . ? C6 C5 C12 C13 0.7(8) . . . . ? C6 C5 C12 C11 -177.3(6) . . . . ? C10 C11 C12 C13 0.7(5) . . . . ? C4 C11 C12 C13 -178.4(5) . . . . ? C10 C11 C12 C5 178.8(5) . . . . ? C4 C11 C12 C5 -0.2(10) . . . . ? C10 N9 C13 C12 1.0(5) . . . . ? C14 N9 C13 C12 -173.1(4) . . . . ? C10 N9 C13 C8 -177.3(5) . . . . ? C14 N9 C13 C8 8.6(8) . . . . ? C5 C12 C13 N9 -179.5(4) . . . . ? C11 C12 C13 N9 -1.0(5) . . . . ? C5 C12 C13 C8 -1.1(7) . . . . ? C11 C12 C13 C8 177.4(4) . . . . ? C7 C8 C13 N9 178.3(4) . . . . ? C7 C8 C13 C12 0.2(7) . . . . ? C10 N9 C14 C16B 125.4(8) . . . 3_656 ? C13 N9 C14 C16B -61.7(8) . . . 3_656 ? C10 N9 C14 C15 62.9(8) . . . . ? C13 N9 C14 C15 -124.1(7) . . . . ? C10 N9 C14 C15B -54.4(9) . . . . ? C13 N9 C14 C15B 118.6(8) . . . . ? C10 N9 C14 C16 -117.8(7) . . . 3_656 ? C13 N9 C14 C16 55.2(8) . . . 3_656 ? C16 C14 C15 C16 1.8(14) 3_656 . . . ? N9 C14 C15 C16 -178.9(6) . . . . ? C14 C15 C16 C14 -1.9(14) . . . 3_656 ? C16B C14 C15B C16B 1.1(16) 3_656 . . . ? N9 C14 C15B C16B -179.1(8) . . . . ? C14 C15B C16B C14 -1.1(17) . . . 3_656 ?