#------------------------------------------------------------------------------ #$Date: 2020-05-07 21:40:48 +0300 (Thu, 07 May 2020) $ #$Revision: 251876 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240481.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_7240481 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 H24 N2' _chemical_formula_sum 'C30 H24 N2' _chemical_formula_weight 412.51 _chemical_melting_point 568 _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 ; 2020-03-16 deposited with the CCDC. 2020-05-06 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.876(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 11.5168(10) _cell_length_b 7.6482(6) _cell_length_c 12.8491(11) _cell_measurement_reflns_used 4948 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 29.45 _cell_measurement_theta_min 2.36 _cell_volume 1131.65(16) _computing_cell_refinement 'APEX3 v2018.1-0(Bruker, 2018)' _computing_data_collection 'APEX3 v2018.1-0(Bruker, 2018)' _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 0.997 _diffrn_measured_fraction_theta_max 0.997 _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 0.1147 _diffrn_reflns_av_unetI/netI 0.0692 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 19288 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.372 _diffrn_reflns_theta_min 2.357 _diffrn_source 'micro-focus X-ray source' _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_T_max 0.7460 _exptl_absorpt_correction_T_min 0.6620 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Sheldrick, 2012)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.211 _exptl_crystal_description platy-prism _exptl_crystal_F_000 436 _exptl_crystal_preparation Luminescent _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF' _exptl_crystal_size_max 0.386 _exptl_crystal_size_mid 0.344 _exptl_crystal_size_min 0.127 _refine_diff_density_max 0.159 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.033 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 200 _refine_ls_number_reflns 2307 _refine_ls_number_restraints 111 _refine_ls_restrained_S_all 1.024 _refine_ls_R_factor_all 0.1660 _refine_ls_R_factor_gt 0.0676 _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^)+(0.0854P)^2^+0.2598P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1503 _refine_ls_wR_factor_ref 0.1967 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1122 _reflns_number_total 2307 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00423e2.cif _cod_data_source_block 117RMB19 _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7240481 _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 0.973 _shelx_estimated_absorpt_t_max 0.991 _shelx_res_file ; TITL 117RMB19 117RMB19.res created by SHELXL-2018/3 at 08:25:00 on 20-Mar-2019 CELL 0.71073 11.5168 7.6482 12.8491 90.000 90.876 90.000 ZERR 2.000 0.0010 0.0006 0.0011 0.000 0.003 0.000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H N UNIT 60 48 4 OMIT 6 3 6 OMIT 6 0 6 OMIT 3 3 6 OMIT 3 6 6 OMIT 3 8 6 OMIT -6 3 3 OMIT 3 3 0 TEMP 25 SIZE 0.127 0.344 0.386 L.S. 20 ACTA HTAB BOND $H CONF LIST 4 FMAP 2 PLAN 5 SIMU 0.01 C1 > C4B DELU 0.005 C1 > C4B WGHT 0.085400 0.259800 FVAR 0.62300 0.61171 PART 1 SAME 0.01 0.01 C5 > C8 C1 1 0.611375 0.338723 0.266413 10.50000 0.09319 0.07728 = 0.07766 0.00178 0.00632 -0.00629 AFIX 43 H1 2 0.659100 0.250243 0.292277 10.50000 -1.20000 AFIX 0 C2 1 0.639401 0.439005 0.180701 10.50000 0.11108 0.09871 = 0.07609 0.00194 0.02115 -0.00825 AFIX 43 H2 2 0.694990 0.399488 0.134521 10.50000 -1.20000 AFIX 0 C3 1 0.584876 0.598022 0.163541 10.50000 0.13232 0.09202 = 0.08622 0.02146 0.02473 -0.01619 AFIX 43 H3 2 0.624244 0.686342 0.129007 10.50000 -1.20000 AFIX 0 C4 1 0.472623 0.628036 0.196904 10.50000 0.12290 0.07936 = 0.07317 0.01760 0.00372 -0.01158 AFIX 43 H4 2 0.424742 0.714234 0.168594 10.50000 -1.20000 AFIX 0 PART 2 C1B 1 0.614170 0.325735 0.279920 10.50000 0.09446 0.08477 = 0.06812 -0.00461 0.01090 -0.01119 AFIX 23 H1A 2 0.605694 0.212258 0.246957 10.50000 -1.20000 H1B 2 0.662758 0.310228 0.341559 10.50000 -1.20000 AFIX 0 C2B 1 0.675208 0.444137 0.207133 10.50000 0.11374 0.09768 = 0.08164 0.00265 0.01369 -0.01843 AFIX 23 H2A 2 0.721098 0.526685 0.247677 10.50000 -1.20000 H2B 2 0.728489 0.375047 0.166298 10.50000 -1.20000 AFIX 0 C3B 1 0.599004 0.542642 0.135586 10.50000 0.13501 0.09335 = 0.07507 0.00309 0.01564 -0.01919 AFIX 23 H3A 2 0.644142 0.636018 0.105007 10.50000 -1.20000 H3B 2 0.574931 0.465115 0.079542 10.50000 -1.20000 AFIX 0 C4B 1 0.496962 0.617895 0.179700 10.50000 0.12291 0.07833 = 0.07217 0.02222 0.00735 -0.01955 AFIX 23 H4A 2 0.438846 0.628109 0.124596 10.50000 -1.20000 H4B 2 0.516262 0.735621 0.202086 10.50000 -1.20000 AFIX 0 PART 0 C5 1 0.241909 0.652030 0.329192 11.00000 0.11219 0.05317 = 0.08917 -0.00417 -0.04457 0.02187 AFIX 43 H5 2 0.236740 0.740665 0.279788 11.00000 -1.20000 AFIX 0 C6 1 0.156773 0.630207 0.401509 11.00000 0.09840 0.08788 = 0.12279 -0.01910 -0.03769 0.04450 AFIX 43 H6 2 0.092055 0.702899 0.399087 11.00000 -1.20000 AFIX 0 C7 1 0.164316 0.504155 0.477379 11.00000 0.07388 0.08969 = 0.11806 -0.00910 -0.00518 0.02539 AFIX 43 H7 2 0.107023 0.497697 0.527461 11.00000 -1.20000 AFIX 0 C8 1 0.256045 0.385951 0.480724 11.00000 0.07157 0.06017 = 0.08497 0.00146 -0.00471 0.00864 AFIX 43 H8 2 0.260020 0.297757 0.530479 11.00000 -1.20000 AFIX 0 N9 3 0.442305 0.309474 0.393633 11.00000 0.06558 0.04100 = 0.06221 0.00563 -0.00561 0.00661 C10 1 0.503013 0.382919 0.311543 11.00000 0.07213 0.04779 = 0.05764 0.00219 -0.00315 -0.00735 C11 1 0.439985 0.522700 0.272718 11.00000 0.09908 0.04415 = 0.06007 0.00587 -0.01738 -0.00978 C12 1 0.337060 0.537293 0.331564 11.00000 0.08686 0.03694 = 0.06453 -0.00434 -0.02794 0.00378 C13 1 0.341010 0.405338 0.406859 11.00000 0.06527 0.03672 = 0.06435 -0.00315 -0.01510 0.00646 C14 1 0.471977 0.152459 0.447963 11.00000 0.05625 0.03654 = 0.05357 0.00249 -0.00712 0.00411 PART 1 C15 1 0.576860 0.137773 0.498569 21.00000 0.06416 0.03851 = 0.06467 -0.00002 -0.01318 -0.00411 AFIX 43 H15 2 0.628726 0.230968 0.498391 21.00000 -1.20000 AFIX 0 C16 1 0.605891 -0.014594 0.549782 21.00000 0.05558 0.04797 = 0.06753 -0.00005 -0.01791 0.00419 AFIX 43 H16 2 0.677923 -0.024932 0.582916 21.00000 -1.20000 AFIX 0 PART 2 C15B 1 0.479495 0.151444 0.553275 -21.00000 0.07812 0.03607 = 0.05070 -0.00662 -0.00691 0.00331 AFIX 43 H15B 2 0.465732 0.254043 0.589924 -21.00000 -1.20000 AFIX 0 C16B 1 0.507225 0.000718 0.606967 -21.00000 0.08430 0.04692 = 0.04468 -0.00235 -0.01111 0.01185 AFIX 43 H16B 2 0.511980 0.001479 0.679284 -21.00000 -1.20000 PART 0 AFIX 0 HKLF 4 REM 117RMB19 REM wR2 = 0.1967, GooF = S = 1.024, Restrained GooF = 1.024 for all data REM R1 = 0.0676 for 1122 Fo > 4sig(Fo) and 0.1660 for all 2307 data REM 200 parameters refined using 111 restraints END WGHT 0.0854 0.2598 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.159, deepest hole -0.179, 1-sigma level 0.033 Q1 1 0.6185 0.6730 0.2182 11.00000 0.05 0.16 Q2 1 0.6251 0.6263 0.0513 11.00000 0.05 0.16 Q3 1 0.6518 0.2041 0.3319 11.00000 0.05 0.15 Q4 1 0.2402 0.7039 0.4447 11.00000 0.05 0.13 Q5 1 0.7758 0.4553 0.1773 11.00000 0.05 0.12 ; _shelx_res_checksum 67483 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 0.611(3) 0.339(3) 0.266(2) 0.083(2) Uani 0.5 1 d D U P A 1 H1 H 0.659100 0.250243 0.292277 0.099 Uiso 0.5 1 calc R U P A 1 C2 C 0.6394(9) 0.4390(16) 0.1807(9) 0.095(2) Uani 0.5 1 d D U P A 1 H2 H 0.694990 0.399488 0.134521 0.114 Uiso 0.5 1 calc R U P A 1 C3 C 0.5849(13) 0.5980(12) 0.1635(9) 0.103(2) Uani 0.5 1 d D U P A 1 H3 H 0.624244 0.686342 0.129007 0.124 Uiso 0.5 1 calc R U P A 1 C4 C 0.4726(13) 0.628(3) 0.1969(16) 0.092(3) Uani 0.5 1 d D U P A 1 H4 H 0.424742 0.714234 0.168594 0.110 Uiso 0.5 1 calc R U P A 1 C1B C 0.614(3) 0.326(3) 0.280(2) 0.082(2) Uani 0.5 1 d . U P A 2 H1A H 0.605694 0.212258 0.246957 0.099 Uiso 0.5 1 calc R U P A 2 H1B H 0.662758 0.310228 0.341559 0.099 Uiso 0.5 1 calc R U P A 2 C2B C 0.6752(10) 0.4441(17) 0.2071(9) 0.098(2) Uani 0.5 1 d . U P A 2 H2A H 0.721098 0.526685 0.247677 0.117 Uiso 0.5 1 calc R U P A 2 H2B H 0.728489 0.375047 0.166298 0.117 Uiso 0.5 1 calc R U P A 2 C3B C 0.5990(12) 0.5426(14) 0.1356(9) 0.101(2) Uani 0.5 1 d . U P A 2 H3A H 0.644142 0.636018 0.105007 0.121 Uiso 0.5 1 calc R U P A 2 H3B H 0.574931 0.465115 0.079542 0.121 Uiso 0.5 1 calc R U P A 2 C4B C 0.4970(13) 0.618(3) 0.1797(16) 0.091(3) Uani 0.5 1 d . U P A 2 H4A H 0.438846 0.628109 0.124596 0.109 Uiso 0.5 1 calc R U P A 2 H4B H 0.516262 0.735621 0.202086 0.109 Uiso 0.5 1 calc R U P A 2 C5 C 0.2419(3) 0.6520(4) 0.3292(3) 0.0853(11) Uani 1 1 d D . . . . H5 H 0.236740 0.740665 0.279788 0.102 Uiso 1 1 calc R U . . . C6 C 0.1568(4) 0.6302(5) 0.4015(3) 0.1034(13) Uani 1 1 d D . . . . H6 H 0.092055 0.702899 0.399087 0.124 Uiso 1 1 calc R U . . . C7 C 0.1643(3) 0.5042(5) 0.4774(3) 0.0939(12) Uani 1 1 d D . . . . H7 H 0.107023 0.497697 0.527461 0.113 Uiso 1 1 calc R U . . . C8 C 0.2560(3) 0.3860(4) 0.4807(3) 0.0723(9) Uani 1 1 d D . . . . H8 H 0.260020 0.297757 0.530479 0.087 Uiso 1 1 calc R U . . . N9 N 0.44231(19) 0.3095(2) 0.39363(18) 0.0563(7) Uani 1 1 d . . . . . C10 C 0.5030(3) 0.3829(3) 0.3115(2) 0.0592(8) Uani 1 1 d . . . . . C11 C 0.4400(3) 0.5227(3) 0.2727(2) 0.0680(9) Uani 1 1 d . . . . . C12 C 0.3371(3) 0.5373(3) 0.3316(2) 0.0631(9) Uani 1 1 d . . . . . C13 C 0.3410(2) 0.4053(3) 0.4069(2) 0.0556(8) Uani 1 1 d . . . . . C14 C 0.4720(2) 0.1525(3) 0.4480(2) 0.0489(7) Uani 1 1 d . . . . . C15 C 0.5769(4) 0.1378(5) 0.4986(4) 0.0559(15) Uani 0.612(5) 1 d . . P B 1 H15 H 0.628726 0.230968 0.498391 0.067 Uiso 0.612(5) 1 calc R U P B 1 C16 C 0.6059(4) -0.0146(5) 0.5498(4) 0.0572(15) Uani 0.612(5) 1 d . . P B 1 H16 H 0.677923 -0.024932 0.582916 0.069 Uiso 0.612(5) 1 calc R U P B 1 C15B C 0.4795(7) 0.1514(8) 0.5533(6) 0.055(2) Uani 0.388(5) 1 d . . P B 2 H15B H 0.465732 0.254043 0.589924 0.066 Uiso 0.388(5) 1 calc R U P B 2 C16B C 0.5072(7) 0.0007(8) 0.6070(6) 0.059(3) Uani 0.388(5) 1 d . . P B 2 H16B H 0.511980 0.001479 0.679284 0.071 Uiso 0.388(5) 1 calc R U P B 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 0.093(4) 0.077(4) 0.078(6) 0.002(3) 0.006(5) -0.006(4) C2 0.111(5) 0.099(4) 0.076(5) 0.002(4) 0.021(4) -0.008(4) C3 0.132(5) 0.092(4) 0.086(5) 0.021(4) 0.025(4) -0.016(4) C4 0.123(6) 0.079(4) 0.073(6) 0.018(4) 0.004(5) -0.012(4) C1B 0.094(4) 0.085(4) 0.068(5) -0.005(3) 0.011(4) -0.011(4) C2B 0.114(5) 0.098(4) 0.082(5) 0.003(4) 0.014(4) -0.018(4) C3B 0.135(5) 0.093(5) 0.075(5) 0.003(3) 0.016(4) -0.019(4) C4B 0.123(6) 0.078(4) 0.072(6) 0.022(4) 0.007(5) -0.020(4) C5 0.112(3) 0.0532(18) 0.089(3) -0.0042(17) -0.045(2) 0.022(2) C6 0.098(3) 0.088(3) 0.123(4) -0.019(3) -0.038(3) 0.044(2) C7 0.074(2) 0.090(3) 0.118(3) -0.009(2) -0.005(2) 0.0254(19) C8 0.072(2) 0.0602(18) 0.085(2) 0.0015(17) -0.0047(19) 0.0086(16) N9 0.0656(15) 0.0410(12) 0.0622(16) 0.0056(11) -0.0056(12) 0.0066(11) C10 0.072(2) 0.0478(15) 0.0576(18) 0.0022(14) -0.0032(16) -0.0074(15) C11 0.099(3) 0.0441(16) 0.060(2) 0.0059(15) -0.0174(19) -0.0098(16) C12 0.087(2) 0.0369(14) 0.065(2) -0.0043(13) -0.0279(18) 0.0038(15) C13 0.0653(18) 0.0367(13) 0.0644(19) -0.0032(13) -0.0151(15) 0.0065(13) C14 0.0562(17) 0.0365(14) 0.0536(19) 0.0025(12) -0.0071(13) 0.0041(12) C15 0.064(3) 0.039(2) 0.065(3) 0.000(2) -0.013(3) -0.004(2) C16 0.056(3) 0.048(3) 0.068(3) 0.000(2) -0.018(3) 0.004(2) C15B 0.078(6) 0.036(4) 0.051(5) -0.007(3) -0.007(4) 0.003(3) C16B 0.084(6) 0.047(4) 0.045(4) -0.002(3) -0.011(4) 0.012(4) 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 C2 C1 C10 114.1(14) . . ? C2 C1 H1 122.9 . . ? C10 C1 H1 122.9 . . ? C1 C2 C3 120.2(10) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C2 C3 C4 121.2(10) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C11 C4 C3 113.8(12) . . ? C11 C4 H4 123.1 . . ? C3 C4 H4 123.1 . . ? C10 C1B C2B 115.5(12) . . ? C10 C1B H1A 108.4 . . ? C2B C1B H1A 108.4 . . ? C10 C1B H1B 108.4 . . ? C2B C1B H1B 108.4 . . ? H1A C1B H1B 107.5 . . ? C3B C2B C1B 115.0(13) . . ? C3B C2B H2A 108.5 . . ? C1B C2B H2A 108.5 . . ? C3B C2B H2B 108.5 . . ? C1B C2B H2B 108.5 . . ? H2A C2B H2B 107.5 . . ? C4B C3B C2B 116.4(10) . . ? C4B C3B H3A 108.2 . . ? C2B C3B H3A 108.2 . . ? C4B C3B H3B 108.2 . . ? C2B C3B H3B 108.2 . . ? H3A C3B H3B 107.3 . . ? C3B C4B C11 118.3(12) . . ? C3B C4B H4A 107.7 . . ? C11 C4B H4A 107.7 . . ? C3B C4B H4B 107.7 . . ? C11 C4B H4B 107.7 . . ? H4A C4B H4B 107.1 . . ? C6 C5 C12 118.4(3) . . ? C6 C5 H5 120.8 . . ? C12 C5 H5 120.8 . . ? C5 C6 C7 121.9(3) . . ? C5 C6 H6 119.0 . . ? C7 C6 H6 119.0 . . ? C6 C7 C8 121.2(4) . . ? C6 C7 H7 119.4 . . ? C8 C7 H7 119.4 . . ? C13 C8 C7 117.0(3) . . ? C13 C8 H8 121.5 . . ? C7 C8 H8 121.5 . . ? C13 N9 C10 108.2(2) . . ? C13 N9 C14 125.4(2) . . ? C10 N9 C14 126.2(2) . . ? C11 C10 N9 108.6(3) . . ? C11 C10 C1B 127.4(6) . . ? N9 C10 C1B 123.9(6) . . ? C11 C10 C1 119.7(5) . . ? N9 C10 C1 131.7(5) . . ? C4 C11 C10 125.7(6) . . ? C4 C11 C12 126.4(6) . . ? C10 C11 C12 107.9(3) . . ? C10 C11 C4B 114.5(6) . . ? C12 C11 C4B 137.6(6) . . ? C13 C12 C5 118.9(3) . . ? C13 C12 C11 107.0(3) . . ? C5 C12 C11 134.0(3) . . ? C8 C13 N9 129.2(2) . . ? C8 C13 C12 122.5(3) . . ? N9 C13 C12 108.3(3) . . ? C15 C14 C16 119.7(3) . 3_656 ? C15B C14 C16B 119.6(4) . 3_656 ? C15 C14 C16B 90.8(4) . 3_656 ? C16 C14 C16B 59.0(4) 3_656 3_656 ? C15B C14 N9 120.3(3) . . ? C15 C14 N9 120.3(3) . . ? C16 C14 N9 120.0(3) 3_656 . ? C16B C14 N9 120.1(4) 3_656 . ? C14 C15 C16 120.2(4) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C14 120.1(4) . 3_656 ? C15 C16 H16 119.9 . . ? C14 C16 H16 119.9 3_656 . ? C14 C15B C16B 121.0(6) . . ? C14 C15B H15B 119.5 . . ? C16B C15B H15B 119.5 . . ? C15B C16B H16B 120.3 . . ? C14 C16B H16B 120.3 3_656 . ? 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 C2 1.384(10) . ? C1 C10 1.42(3) . ? C1 H1 0.9300 . ? C2 C3 1.385(9) . ? C2 H2 0.9300 . ? C3 C4 1.387(9) . ? C3 H3 0.9300 . ? C4 C11 1.32(2) . ? C4 H4 0.9300 . ? C1B C10 1.42(3) . ? C1B C2B 1.486(16) . ? C1B H1A 0.9700 . ? C1B H1B 0.9700 . ? C2B C3B 1.469(15) . ? C2B H2A 0.9700 . ? C2B H2B 0.9700 . ? C3B C4B 1.433(12) . ? C3B H3A 0.9700 . ? C3B H3B 0.9700 . ? C4B C11 1.553(18) . ? C4B H4A 0.9700 . ? C4B H4B 0.9700 . ? C5 C6 1.371(5) . ? C5 C12 1.404(4) . ? C5 H5 0.9300 . ? C6 C7 1.373(5) . ? C6 H6 0.9300 . ? C7 C8 1.391(4) . ? C7 H7 0.9300 . ? C8 C13 1.382(4) . ? C8 H8 0.9300 . ? N9 C13 1.390(3) . ? N9 C10 1.393(3) . ? N9 C14 1.428(3) . ? C10 C11 1.381(4) . ? C11 C12 1.420(4) . ? C12 C13 1.398(4) . ? C14 C15B 1.355(7) . ? C14 C15 1.368(5) . ? C14 C16 1.385(5) 3_656 ? C14 C16B 1.390(7) 3_656 ? C15 C16 1.377(6) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C15B C16B 1.378(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 19(3) . . . . ? C1 C2 C3 C4 -29(2) . . . . ? C2 C3 C4 C11 22(2) . . . . ? C10 C1B C2B C3B -32(3) . . . . ? C1B C2B C3B C4B 43(2) . . . . ? C2B C3B C4B C11 -31(2) . . . . ? C12 C5 C6 C7 2.2(5) . . . . ? C5 C6 C7 C8 -3.7(6) . . . . ? C6 C7 C8 C13 2.3(5) . . . . ? C13 N9 C10 C11 -0.6(3) . . . . ? C14 N9 C10 C11 173.4(2) . . . . ? C13 N9 C10 C1B 176.0(17) . . . . ? C14 N9 C10 C1B -10.0(18) . . . . ? C13 N9 C10 C1 179.1(19) . . . . ? C14 N9 C10 C1 -6.9(19) . . . . ? C2B C1B C10 C11 9(3) . . . . ? C2B C1B C10 N9 -167.1(12) . . . . ? C2 C1 C10 C11 -4(3) . . . . ? C2 C1 C10 N9 176.5(10) . . . . ? C3 C4 C11 C10 -6(2) . . . . ? C3 C4 C11 C12 171.0(8) . . . . ? N9 C10 C11 C4 177.3(12) . . . . ? C1 C10 C11 C4 -2(2) . . . . ? N9 C10 C11 C12 -0.2(3) . . . . ? C1B C10 C11 C12 -176.6(18) . . . . ? C1 C10 C11 C12 -179.9(16) . . . . ? N9 C10 C11 C4B -179.7(9) . . . . ? C1B C10 C11 C4B 4(2) . . . . ? C3B C4B C11 C10 7.2(18) . . . . ? C3B C4B C11 C12 -172.1(7) . . . . ? C6 C5 C12 C13 0.3(4) . . . . ? C6 C5 C12 C11 -178.2(3) . . . . ? C4 C11 C12 C13 -176.6(12) . . . . ? C10 C11 C12 C13 0.8(3) . . . . ? C4B C11 C12 C13 -179.8(12) . . . . ? C4 C11 C12 C5 2.0(13) . . . . ? C10 C11 C12 C5 179.5(3) . . . . ? C4B C11 C12 C5 -1.1(13) . . . . ? C7 C8 C13 N9 178.4(3) . . . . ? C7 C8 C13 C12 0.2(4) . . . . ? C10 N9 C13 C8 -177.3(3) . . . . ? C14 N9 C13 C8 8.7(4) . . . . ? C10 N9 C13 C12 1.1(3) . . . . ? C14 N9 C13 C12 -172.9(2) . . . . ? C5 C12 C13 C8 -1.5(4) . . . . ? C11 C12 C13 C8 177.3(3) . . . . ? C5 C12 C13 N9 179.9(2) . . . . ? C11 C12 C13 N9 -1.2(3) . . . . ? C13 N9 C14 C15B -58.3(5) . . . . ? C10 N9 C14 C15B 128.7(5) . . . . ? C13 N9 C14 C15 -127.6(4) . . . . ? C10 N9 C14 C15 59.4(4) . . . . ? C13 N9 C14 C16 51.9(4) . . . 3_656 ? C10 N9 C14 C16 -121.0(4) . . . 3_656 ? C13 N9 C14 C16B 121.4(5) . . . 3_656 ? C10 N9 C14 C16B -51.6(5) . . . 3_656 ? C16 C14 C15 C16 1.3(7) 3_656 . . . ? N9 C14 C15 C16 -179.2(3) . . . . ? C14 C15 C16 C14 -1.3(7) . . . 3_656 ? C16B C14 C15B C16B -0.1(11) 3_656 . . . ? N9 C14 C15B C16B 179.5(5) . . . . ? C14 C15B C16B C14 0.1(11) . . . 3_656 ?