#------------------------------------------------------------------------------ #$Date: 2020-05-07 21:40:48 +0300 (Thu, 07 May 2020) $ #$Revision: 251876 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240480.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_7240480 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 91.539(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 11.4789(10) _cell_length_b 7.7861(6) _cell_length_c 12.4833(11) _cell_measurement_reflns_used 5718 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 30.03 _cell_measurement_theta_min 2.38 _cell_volume 1115.30(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\"i?1/2bschle 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 100(2) _diffrn_detector_area_resol_mean 52.0833 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker D8 Venture \k-geometry diffractometer 208039-01' _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 0.0486 _diffrn_reflns_av_unetI/netI 0.0472 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 13999 _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 30.088 _diffrn_reflns_theta_min 2.443 _diffrn_source 'micro-focus X-ray source' _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_T_max 0.7460 _exptl_absorpt_correction_T_min 0.6488 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Sheldrick, 2012)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.240 _exptl_crystal_description prism _exptl_crystal_F_000 444 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF' _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.236 _exptl_crystal_size_min 0.180 _refine_diff_density_max 0.460 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.077 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 281 _refine_ls_number_reflns 3260 _refine_ls_number_restraints 789 _refine_ls_restrained_S_all 0.998 _refine_ls_R_factor_all 0.1498 _refine_ls_R_factor_gt 0.0828 _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^)+(0.1325P)^2^+0.2084P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2076 _refine_ls_wR_factor_ref 0.2513 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1696 _reflns_number_total 3260 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00423e2.cif _cod_data_source_block 208RMB19 _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7240480 _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 0.979 _shelx_estimated_absorpt_t_max 0.987 _shelx_res_file ; TITL 208RMB19 208RMB19.res created by SHELXL-2018/3 at 13:16:07 on 16-May-2019 CELL 0.71073 11.4789 7.7861 12.4833 90 91.539 90 ZERR 2 0.001 0.0006 0.0011 0 0.003 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N UNIT 60 56 4 OMIT -3 0 9 OMIT -3 1 4 OMIT 1 4 1 OMIT 3 1 2 OMIT -4 2 1 OMIT -2 3 2 OMIT 0 1 4 TEMP -173.22 SIZE 0.18 0.236 0.3 ACTA CONF L.S. 20 LIST 4 HTAB BOND $H FMAP 2 PLAN 5 DELU 0.005 C1 > C13B SIMU 0.01 C1 > C13B ISOR 0.01 WGHT 0.132500 0.208400 FVAR 0.54122 0.53655 PART 1 C1 1 0.625318 0.309874 0.271156 21.00000 0.05964 0.06735 = 0.06008 0.00078 0.01326 0.00266 AFIX 23 H1A 2 0.615137 0.206725 0.225487 21.00000 -1.20000 H1B 2 0.674006 0.278073 0.334752 21.00000 -1.20000 AFIX 0 C2 1 0.684272 0.450427 0.209226 21.00000 0.07201 0.08861 = 0.06954 0.01072 0.00881 -0.00717 AFIX 23 H2A 2 0.750404 0.400845 0.170389 21.00000 -1.20000 H2B 2 0.715975 0.537208 0.260114 21.00000 -1.20000 AFIX 0 C3 1 0.600845 0.538371 0.128862 21.00000 0.08734 0.06660 = 0.04836 0.00852 0.00828 -0.01055 AFIX 23 H3A 2 0.644194 0.628224 0.090425 21.00000 -1.20000 H3B 2 0.573799 0.452474 0.075270 21.00000 -1.20000 AFIX 0 C4 1 0.502563 0.614311 0.175158 21.00000 0.07264 0.06557 = 0.05916 0.01086 -0.00233 -0.00917 AFIX 23 H4A 2 0.440761 0.628591 0.119016 21.00000 -1.20000 H4B 2 0.524207 0.730079 0.201765 21.00000 -1.20000 AFIX 0 C5 1 0.261645 0.660470 0.317053 21.00000 0.06515 0.04706 = 0.05746 -0.00134 -0.01408 0.01107 AFIX 43 H5 2 0.258916 0.746544 0.263106 21.00000 -1.20000 AFIX 0 C6 1 0.177005 0.648569 0.394237 21.00000 0.07742 0.06142 = 0.08643 0.01375 0.00652 0.02927 AFIX 43 H6 2 0.119303 0.735898 0.396179 21.00000 -1.20000 AFIX 0 C7 1 0.171855 0.516270 0.468795 21.00000 0.05696 0.05882 = 0.07518 0.00442 0.00490 0.01569 AFIX 43 H7 2 0.107195 0.507971 0.514442 21.00000 -1.20000 AFIX 0 C8 1 0.263009 0.393839 0.476711 21.00000 0.05425 0.04197 = 0.06077 -0.00039 0.00274 0.00896 AFIX 43 H8 2 0.264781 0.306873 0.530108 21.00000 -1.20000 AFIX 0 N9 3 0.449499 0.306661 0.389605 21.00000 0.04816 0.03960 = 0.04960 -0.00148 -0.00229 0.00818 C10 1 0.511567 0.371910 0.304857 21.00000 0.05418 0.04216 = 0.04840 0.00016 -0.00243 0.00050 C11 1 0.455320 0.514084 0.264315 21.00000 0.06013 0.04635 = 0.04521 -0.00197 -0.00488 -0.00058 C12 1 0.352567 0.536555 0.323371 21.00000 0.05760 0.03542 = 0.04449 -0.00458 -0.00960 0.00418 C13 1 0.350262 0.408794 0.401105 21.00000 0.04777 0.03847 = 0.04794 -0.00574 -0.00783 0.00612 SAME 0.01 0.01 C1 > C13 PART 2 C1B 1 0.604378 0.344672 0.275073 -21.00000 0.05824 0.05675 = 0.06789 0.00275 0.00180 0.00185 AFIX 23 H1C 2 0.604980 0.220667 0.257568 -21.00000 -1.20000 H1D 2 0.665186 0.365827 0.331265 -21.00000 -1.20000 AFIX 0 C2B 1 0.631622 0.447010 0.176520 -21.00000 0.07382 0.08435 = 0.07446 0.00684 0.00795 -0.00923 AFIX 23 H2C 2 0.598723 0.387025 0.112659 -21.00000 -1.20000 H2D 2 0.717223 0.452454 0.169329 -21.00000 -1.20000 AFIX 0 C3B 1 0.583219 0.629311 0.179161 -21.00000 0.09121 0.08383 = 0.09151 0.02858 0.00530 -0.01024 AFIX 23 H3C 2 0.624546 0.693340 0.237202 -21.00000 -1.20000 H3D 2 0.600866 0.686498 0.110647 -21.00000 -1.20000 AFIX 0 C4B 1 0.462346 0.641443 0.195119 -21.00000 0.07988 0.05953 = 0.07210 0.01266 -0.00579 -0.01231 AFIX 23 H4C 2 0.420034 0.612552 0.127350 -21.00000 -1.20000 H4D 2 0.442826 0.761466 0.213697 -21.00000 -1.20000 AFIX 0 C5B 1 0.221999 0.639978 0.341464 -21.00000 0.06070 0.04205 = 0.05222 -0.00526 -0.01510 0.01384 AFIX 43 H5B 2 0.214923 0.734042 0.293258 -21.00000 -1.20000 AFIX 0 C6B 1 0.136060 0.603566 0.415261 -21.00000 0.05684 0.04579 = 0.06815 -0.00643 -0.01090 0.00987 AFIX 43 H6B 2 0.065684 0.667799 0.412306 -21.00000 -1.20000 AFIX 0 C7B 1 0.149989 0.475787 0.493400 -21.00000 0.06093 0.05902 = 0.07017 -0.00083 0.00296 0.01858 AFIX 43 H7B 2 0.094271 0.465373 0.547936 -21.00000 -1.20000 AFIX 0 C8B 1 0.245520 0.362480 0.492214 -21.00000 0.05516 0.04758 = 0.05391 -0.00175 -0.00438 0.01097 AFIX 43 H8B 2 0.253056 0.269753 0.541374 -21.00000 -1.20000 AFIX 0 N9B 3 0.432945 0.306767 0.396773 -21.00000 0.04757 0.03659 = 0.04723 0.00081 -0.00682 0.00169 C10B 1 0.490273 0.391883 0.315719 -21.00000 0.05437 0.04299 = 0.05277 -0.00063 -0.00585 -0.00318 C11B 1 0.422454 0.526617 0.280634 -21.00000 0.05892 0.03857 = 0.05577 0.00308 -0.01221 -0.00291 C12B 1 0.320562 0.529423 0.342011 -21.00000 0.05693 0.03653 = 0.05026 -0.00568 -0.01265 0.00249 C13B 1 0.328505 0.393685 0.414985 -21.00000 0.05284 0.03301 = 0.04771 -0.00544 -0.01231 0.00968 PART 0 C14 1 0.471259 0.151345 0.447268 11.00000 0.04608 0.03610 = 0.04377 -0.00242 -0.00334 0.00626 SIMU 0.01 C15 > C16B DELU 0.005 C15 > C16B PART 1 C15 1 0.576128 0.137868 0.500624 21.00000 0.05101 0.03800 = 0.05099 -0.00823 -0.00770 0.00010 AFIX 43 H15 2 0.628440 0.232436 0.502174 21.00000 -1.20000 AFIX 0 C16 1 0.606304 -0.012855 0.552317 21.00000 0.05012 0.04178 = 0.05458 -0.00651 -0.01096 0.00419 AFIX 43 H16 2 0.680227 -0.022671 0.587857 21.00000 -1.20000 AFIX 0 SAME 0.01 0.04 C15 C16 PART 2 C15B 1 0.493627 0.000844 0.389794 -21.00000 0.04357 0.03872 = 0.03469 -0.00393 -0.00142 0.00303 AFIX 43 H15B 2 0.490677 0.001992 0.313671 -21.00000 -1.20000 AFIX 0 C16B 1 0.520045 -0.149536 0.444432 -21.00000 0.04327 0.03367 = 0.04383 -0.00648 -0.00210 0.00673 AFIX 43 H16B 2 0.532193 -0.252518 0.405476 -21.00000 -1.20000 PART 0 AFIX 0 HKLF 4 REM 208RMB19 REM wR2 = 0.2513, GooF = S = 1.022, Restrained GooF = 0.998 for all data REM R1 = 0.0828 for 1696 Fo > 4sig(Fo) and 0.1498 for all 3260 data REM 281 parameters refined using 789 restraints END WGHT 0.1325 0.2084 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.460, deepest hole -0.164, 1-sigma level 0.077 Q1 1 0.2148 0.7007 0.4392 11.00000 0.05 0.46 Q2 1 0.6235 0.4745 0.1333 11.00000 0.05 0.30 Q3 1 0.5626 0.5534 0.1381 11.00000 0.05 0.30 Q4 1 0.1989 0.4238 0.4652 11.00000 0.05 0.28 Q5 1 0.1748 0.5334 0.4367 11.00000 0.05 0.27 ; _shelx_res_checksum 24503 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 0.6253(7) 0.3099(10) 0.2712(8) 0.0621(14) Uani 0.537(3) 1 d D U P A 1 H1A H 0.615137 0.206725 0.225487 0.075 Uiso 0.537(3) 1 calc R U P A 1 H1B H 0.674006 0.278073 0.334752 0.075 Uiso 0.537(3) 1 calc R U P A 1 C2 C 0.6843(5) 0.4504(8) 0.2092(5) 0.0766(13) Uani 0.537(3) 1 d D U P A 1 H2A H 0.750404 0.400845 0.170389 0.092 Uiso 0.537(3) 1 calc R U P A 1 H2B H 0.715975 0.537208 0.260114 0.092 Uiso 0.537(3) 1 calc R U P A 1 C3 C 0.6008(5) 0.5384(8) 0.1289(4) 0.0673(11) Uani 0.537(3) 1 d D U P A 1 H3A H 0.644194 0.628224 0.090425 0.081 Uiso 0.537(3) 1 calc R U P A 1 H3B H 0.573799 0.452474 0.075270 0.081 Uiso 0.537(3) 1 calc R U P A 1 C4 C 0.5026(6) 0.6143(8) 0.1752(5) 0.0659(13) Uani 0.537(3) 1 d D U P A 1 H4A H 0.440761 0.628591 0.119016 0.079 Uiso 0.537(3) 1 calc R U P A 1 H4B H 0.524207 0.730079 0.201765 0.079 Uiso 0.537(3) 1 calc R U P A 1 C5 C 0.2616(5) 0.6605(8) 0.3171(5) 0.0568(13) Uani 0.537(3) 1 d D U P A 1 H5 H 0.258916 0.746544 0.263106 0.068 Uiso 0.537(3) 1 calc R U P A 1 C6 C 0.1770(6) 0.6486(8) 0.3942(6) 0.0750(16) Uani 0.537(3) 1 d D U P A 1 H6 H 0.119303 0.735898 0.396179 0.090 Uiso 0.537(3) 1 calc R U P A 1 C7 C 0.1719(6) 0.5163(9) 0.4688(6) 0.0636(14) Uani 0.537(3) 1 d D U P A 1 H7 H 0.107195 0.507971 0.514442 0.076 Uiso 0.537(3) 1 calc R U P A 1 C8 C 0.2630(7) 0.3938(10) 0.4767(7) 0.0523(14) Uani 0.537(3) 1 d D U P A 1 H8 H 0.264781 0.306873 0.530108 0.063 Uiso 0.537(3) 1 calc R U P A 1 N9 N 0.4495(10) 0.3067(17) 0.3896(12) 0.0459(13) Uani 0.537(3) 1 d D U P A 1 C10 C 0.5116(6) 0.3719(10) 0.3049(7) 0.0483(12) Uani 0.537(3) 1 d D U P A 1 C11 C 0.4553(5) 0.5141(9) 0.2643(5) 0.0507(11) Uani 0.537(3) 1 d D U P A 1 C12 C 0.3526(5) 0.5366(8) 0.3234(5) 0.0460(11) Uani 0.537(3) 1 d D U P A 1 C13 C 0.3503(6) 0.4088(11) 0.4011(7) 0.0449(12) Uani 0.537(3) 1 d D U P A 1 C1B C 0.6044(7) 0.3447(11) 0.2751(9) 0.0610(15) Uani 0.463(3) 1 d D U P A 2 H1C H 0.604980 0.220667 0.257568 0.073 Uiso 0.463(3) 1 calc R U P A 2 H1D H 0.665186 0.365827 0.331265 0.073 Uiso 0.463(3) 1 calc R U P A 2 C2B C 0.6316(7) 0.4470(9) 0.1765(6) 0.0774(15) Uani 0.463(3) 1 d D U P A 2 H2C H 0.598723 0.387025 0.112659 0.093 Uiso 0.463(3) 1 calc R U P A 2 H2D H 0.717223 0.452454 0.169329 0.093 Uiso 0.463(3) 1 calc R U P A 2 C3B C 0.5832(6) 0.6293(9) 0.1792(7) 0.0888(16) Uani 0.463(3) 1 d D U P A 2 H3C H 0.624546 0.693340 0.237202 0.107 Uiso 0.463(3) 1 calc R U P A 2 H3D H 0.600866 0.686498 0.110647 0.107 Uiso 0.463(3) 1 calc R U P A 2 C4B C 0.4623(6) 0.6414(10) 0.1951(6) 0.0706(15) Uani 0.463(3) 1 d D U P A 2 H4C H 0.420034 0.612552 0.127350 0.085 Uiso 0.463(3) 1 calc R U P A 2 H4D H 0.442826 0.761466 0.213697 0.085 Uiso 0.463(3) 1 calc R U P A 2 C5B C 0.2220(6) 0.6400(9) 0.3415(6) 0.0520(14) Uani 0.463(3) 1 d D U P A 2 H5B H 0.214923 0.734042 0.293258 0.062 Uiso 0.463(3) 1 calc R U P A 2 C6B C 0.1361(5) 0.6036(8) 0.4153(6) 0.0572(14) Uani 0.463(3) 1 d D U P A 2 H6B H 0.065684 0.667799 0.412306 0.069 Uiso 0.463(3) 1 calc R U P A 2 C7B C 0.1500(7) 0.4758(10) 0.4934(7) 0.0634(16) Uani 0.463(3) 1 d D U P A 2 H7B H 0.094271 0.465373 0.547936 0.076 Uiso 0.463(3) 1 calc R U P A 2 C8B C 0.2455(8) 0.3625(13) 0.4922(8) 0.0523(15) Uani 0.463(3) 1 d D U P A 2 H8B H 0.253056 0.269753 0.541374 0.063 Uiso 0.463(3) 1 calc R U P A 2 N9B N 0.4329(11) 0.3068(19) 0.3968(13) 0.0439(14) Uani 0.463(3) 1 d D U P A 2 C10B C 0.4903(7) 0.3919(12) 0.3157(9) 0.0502(13) Uani 0.463(3) 1 d D U P A 2 C11B C 0.4225(6) 0.5266(9) 0.2806(6) 0.0513(13) Uani 0.463(3) 1 d D U P A 2 C12B C 0.3206(6) 0.5294(10) 0.3420(7) 0.0482(13) Uani 0.463(3) 1 d D U P A 2 C13B C 0.3285(7) 0.3937(12) 0.4150(8) 0.0448(13) Uani 0.463(3) 1 d D U P A 2 C14 C 0.47126(17) 0.1513(2) 0.44727(15) 0.0421(5) Uani 1 1 d . U . . . C15 C 0.5761(3) 0.1379(5) 0.5006(3) 0.0468(10) Uani 0.537(3) 1 d D U P A 1 H15 H 0.628440 0.232436 0.502174 0.056 Uiso 0.537(3) 1 calc R U P A 1 C16 C 0.6063(3) -0.0129(5) 0.5523(3) 0.0490(10) Uani 0.537(3) 1 d D U P A 1 H16 H 0.680227 -0.022671 0.587857 0.059 Uiso 0.537(3) 1 calc R U P A 1 C15B C 0.4936(3) 0.0008(5) 0.3898(3) 0.0390(9) Uani 0.463(3) 1 d D U P A 2 H15B H 0.490677 0.001992 0.313671 0.047 Uiso 0.463(3) 1 calc R U P A 2 C16B C 0.5200(4) -0.1495(5) 0.4444(3) 0.0403(10) Uani 0.463(3) 1 d D U P A 2 H16B H 0.532193 -0.252518 0.405476 0.048 Uiso 0.463(3) 1 calc R U P A 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 0.060(3) 0.067(3) 0.060(2) 0.001(2) 0.013(2) 0.003(2) C2 0.072(3) 0.089(3) 0.070(3) 0.011(2) 0.009(2) -0.007(2) C3 0.087(3) 0.067(3) 0.048(2) 0.0085(19) 0.0083(19) -0.011(2) C4 0.073(3) 0.066(3) 0.059(2) 0.011(2) -0.002(2) -0.009(2) C5 0.065(3) 0.047(2) 0.057(3) -0.0013(19) -0.014(2) 0.011(2) C6 0.077(3) 0.061(3) 0.086(3) 0.014(3) 0.007(3) 0.029(3) C7 0.057(3) 0.059(3) 0.075(3) 0.004(2) 0.005(2) 0.016(2) C8 0.054(3) 0.042(3) 0.061(3) 0.000(2) 0.003(2) 0.009(2) N9 0.048(3) 0.040(2) 0.050(3) -0.0015(19) -0.002(2) 0.008(2) C10 0.054(3) 0.042(2) 0.048(2) 0.000(2) -0.0024(18) 0.0005(18) C11 0.060(3) 0.046(2) 0.045(2) -0.0020(17) -0.0049(18) -0.0006(19) C12 0.058(3) 0.0354(19) 0.044(2) -0.0046(16) -0.0096(19) 0.004(2) C13 0.048(2) 0.038(2) 0.048(2) -0.0057(17) -0.0078(17) 0.006(2) C1B 0.058(3) 0.057(3) 0.068(3) 0.003(3) 0.002(2) 0.002(2) C2B 0.074(3) 0.084(3) 0.074(3) 0.007(3) 0.008(3) -0.009(3) C3B 0.091(3) 0.084(3) 0.092(3) 0.029(3) 0.005(3) -0.010(3) C4B 0.080(3) 0.060(3) 0.072(3) 0.013(2) -0.006(3) -0.012(2) C5B 0.061(3) 0.042(2) 0.052(3) -0.005(2) -0.015(2) 0.014(2) C6B 0.057(3) 0.046(3) 0.068(3) -0.006(2) -0.011(2) 0.010(2) C7B 0.061(3) 0.059(3) 0.070(3) -0.001(2) 0.003(2) 0.019(3) C8B 0.055(3) 0.048(3) 0.054(3) -0.002(2) -0.004(2) 0.011(3) N9B 0.048(3) 0.037(2) 0.047(3) 0.001(2) -0.007(2) 0.002(2) C10B 0.054(3) 0.043(3) 0.053(3) -0.001(2) -0.006(2) -0.003(2) C11B 0.059(3) 0.039(2) 0.056(3) 0.003(2) -0.012(2) -0.003(2) C12B 0.057(3) 0.037(2) 0.050(3) -0.0057(19) -0.013(2) 0.002(2) C13B 0.053(3) 0.033(2) 0.048(3) -0.0054(19) -0.012(2) 0.010(2) C14 0.0461(10) 0.0361(10) 0.0438(10) -0.0024(8) -0.0033(8) 0.0063(8) C15 0.051(2) 0.0380(18) 0.051(2) -0.0082(15) -0.0077(16) 0.0001(15) C16 0.050(2) 0.0418(19) 0.055(2) -0.0065(15) -0.0110(17) 0.0042(16) C15B 0.044(2) 0.0387(19) 0.0347(18) -0.0039(15) -0.0014(16) 0.0030(16) C16B 0.043(2) 0.0337(19) 0.044(2) -0.0065(15) -0.0021(17) 0.0067(16) 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 108.9(4) . . ? C10 C1 H1A 109.9 . . ? C2 C1 H1A 109.9 . . ? C10 C1 H1B 109.9 . . ? C2 C1 H1B 109.9 . . ? H1A C1 H1B 108.3 . . ? C1 C2 C3 112.3(5) . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2B 109.2 . . ? C3 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C4 C3 C2 114.3(4) . . ? C4 C3 H3A 108.7 . . ? C2 C3 H3A 108.7 . . ? C4 C3 H3B 108.7 . . ? C2 C3 H3B 108.7 . . ? H3A C3 H3B 107.6 . . ? C3 C4 C11 113.7(4) . . ? C3 C4 H4A 108.8 . . ? C11 C4 H4A 108.8 . . ? C3 C4 H4B 108.8 . . ? C11 C4 H4B 108.8 . . ? H4A C4 H4B 107.7 . . ? C6 C5 C12 116.2(4) . . ? C6 C5 H5 121.9 . . ? C12 C5 H5 121.9 . . ? C5 C6 C7 123.8(4) . . ? C5 C6 H6 118.1 . . ? C7 C6 H6 118.1 . . ? C6 C7 C8 120.0(5) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C13 C8 C7 115.9(4) . . ? C13 C8 H8 122.0 . . ? C7 C8 H8 122.0 . . ? C10 N9 C13 107.8(3) . . ? C10 N9 C14 127.5(4) . . ? C13 N9 C14 124.2(4) . . ? C11 C10 N9 109.3(4) . . ? C11 C10 C1 125.1(4) . . ? N9 C10 C1 125.3(4) . . ? C10 C11 C12 107.3(3) . . ? C10 C11 C4 121.8(4) . . ? C12 C11 C4 130.9(4) . . ? C13 C12 C11 107.8(3) . . ? C13 C12 C5 119.8(4) . . ? C11 C12 C5 132.4(4) . . ? C12 C13 C8 123.9(4) . . ? C12 C13 N9 107.7(4) . . ? C8 C13 N9 128.4(4) . . ? C10B C1B C2B 111.0(5) . . ? C10B C1B H1C 109.4 . . ? C2B C1B H1C 109.4 . . ? C10B C1B H1D 109.4 . . ? C2B C1B H1D 109.4 . . ? H1C C1B H1D 108.0 . . ? C1B C2B C3B 113.0(6) . . ? C1B C2B H2C 109.0 . . ? C3B C2B H2C 109.0 . . ? C1B C2B H2D 109.0 . . ? C3B C2B H2D 109.0 . . ? H2C C2B H2D 107.8 . . ? C4B C3B C2B 115.2(6) . . ? C4B C3B H3C 108.5 . . ? C2B C3B H3C 108.5 . . ? C4B C3B H3D 108.5 . . ? C2B C3B H3D 108.5 . . ? H3C C3B H3D 107.5 . . ? C3B C4B C11B 112.8(5) . . ? C3B C4B H4C 109.0 . . ? C11B C4B H4C 109.0 . . ? C3B C4B H4D 109.0 . . ? C11B C4B H4D 109.0 . . ? H4C C4B H4D 107.8 . . ? C6B C5B C12B 116.7(5) . . ? C6B C5B H5B 121.6 . . ? C12B C5B H5B 121.6 . . ? C5B C6B C7B 122.3(4) . . ? C5B C6B H6B 118.8 . . ? C7B C6B H6B 118.8 . . ? C6B C7B C8B 120.8(5) . . ? C6B C7B H7B 119.6 . . ? C8B C7B H7B 119.6 . . ? C13B C8B C7B 116.4(5) . . ? C13B C8B H8B 121.8 . . ? C7B C8B H8B 121.8 . . ? C10B N9B C13B 108.2(4) . . ? C10B N9B C14 125.4(4) . . ? C13B N9B C14 126.3(4) . . ? C11B C10B N9B 108.8(4) . . ? C11B C10B C1B 125.9(4) . . ? N9B C10B C1B 125.3(4) . . ? C10B C11B C12B 108.0(4) . . ? C10B C11B C4B 120.7(5) . . ? C12B C11B C4B 131.3(4) . . ? C13B C12B C11B 107.5(4) . . ? C13B C12B C5B 120.0(5) . . ? C11B C12B C5B 132.5(5) . . ? C8B C13B C12B 123.3(4) . . ? C8B C13B N9B 129.2(4) . . ? C12B C13B N9B 107.5(4) . . ? C15 C14 C16 119.5(2) . 3_656 ? C16B C14 C15B 119.6(2) 3_656 . ? C15 C14 N9 116.9(8) . . ? C16 C14 N9 123.6(8) 3_656 . ? C16B C14 N9B 117.6(8) 3_656 . ? C15B C14 N9B 122.8(9) . . ? C14 C15 C16 120.1(3) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 C14 120.4(3) . 3_656 ? C15 C16 H16 119.8 . . ? C14 C16 H16 119.8 3_656 . ? C16B C15B C14 119.7(3) . . ? C16B C15B H15B 120.1 . . ? C14 C15B H15B 120.1 . . ? C14 C16B C15B 120.7(3) 3_656 . ? C14 C16B H16B 119.7 3_656 . ? C15B C16B H16B 119.7 . . ? 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 1.464(5) . ? C1 C2 1.510(6) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.530(7) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.411(7) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C11 1.475(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.390(7) . ? C5 C12 1.422(5) . ? C5 H5 0.9500 . ? C6 C7 1.391(7) . ? C6 H6 0.9500 . ? C7 C8 1.417(5) . ? C7 H7 0.9500 . ? C8 C13 1.399(6) . ? C8 H8 0.9500 . ? N9 C10 1.388(5) . ? N9 C13 1.400(5) . ? N9 C14 1.426(6) . ? C10 C11 1.371(5) . ? C11 C12 1.418(6) . ? C12 C13 1.390(5) . ? C1B C10B 1.464(6) . ? C1B C2B 1.506(7) . ? C1B H1C 0.9900 . ? C1B H1D 0.9900 . ? C2B C3B 1.525(8) . ? C2B H2C 0.9900 . ? C2B H2D 0.9900 . ? C3B C4B 1.410(7) . ? C3B H3C 0.9900 . ? C3B H3D 0.9900 . ? C4B C11B 1.475(6) . ? C4B H4C 0.9900 . ? C4B H4D 0.9900 . ? C5B C6B 1.397(8) . ? C5B C12B 1.421(6) . ? C5B H5B 0.9500 . ? C6B C7B 1.399(7) . ? C6B H6B 0.9500 . ? C7B C8B 1.408(6) . ? C7B H7B 0.9500 . ? C8B C13B 1.395(6) . ? C8B H8B 0.9500 . ? N9B C10B 1.390(5) . ? N9B C13B 1.401(5) . ? N9B C14 1.428(6) . ? C10B C11B 1.371(6) . ? C11B C12B 1.415(7) . ? C12B C13B 1.397(5) . ? C14 C16B 1.353(4) 3_656 ? C14 C15 1.364(4) . ? C14 C16 1.398(4) 3_656 ? C14 C15B 1.401(4) . ? C15 C16 1.379(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C15B C16B 1.385(5) . ? C15B H15B 0.9500 . ? C16B H16B 0.9500 . ? 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 -44.1(10) . . . . ? C1 C2 C3 C4 58.8(8) . . . . ? C2 C3 C4 C11 -37.6(8) . . . . ? C12 C5 C6 C7 -5.8(11) . . . . ? C5 C6 C7 C8 7.0(12) . . . . ? C6 C7 C8 C13 -4.5(13) . . . . ? C13 N9 C10 C11 1.2(16) . . . . ? C14 N9 C10 C11 173.5(16) . . . . ? C13 N9 C10 C1 175.3(12) . . . . ? C14 N9 C10 C1 -12(3) . . . . ? C2 C1 C10 C11 15.4(14) . . . . ? C2 C1 C10 N9 -157.8(13) . . . . ? N9 C10 C11 C12 -1.7(13) . . . . ? C1 C10 C11 C12 -175.8(10) . . . . ? N9 C10 C11 C4 178.3(11) . . . . ? C1 C10 C11 C4 4.1(14) . . . . ? C3 C4 C11 C10 7.3(11) . . . . ? C3 C4 C11 C12 -172.8(8) . . . . ? C10 C11 C12 C13 1.5(10) . . . . ? C4 C11 C12 C13 -178.4(9) . . . . ? C10 C11 C12 C5 -179.9(9) . . . . ? C4 C11 C12 C5 0.1(15) . . . . ? C6 C5 C12 C13 2.6(11) . . . . ? C6 C5 C12 C11 -175.8(9) . . . . ? C11 C12 C13 C8 178.0(10) . . . . ? C5 C12 C13 C8 -0.8(14) . . . . ? C11 C12 C13 N9 -0.8(12) . . . . ? C5 C12 C13 N9 -179.6(11) . . . . ? C7 C8 C13 C12 1.7(15) . . . . ? C7 C8 C13 N9 -179.8(13) . . . . ? C10 N9 C13 C12 -0.2(16) . . . . ? C14 N9 C13 C12 -172.8(15) . . . . ? C10 N9 C13 C8 -179.0(12) . . . . ? C14 N9 C13 C8 8(2) . . . . ? C10B C1B C2B C3B 34.2(12) . . . . ? C1B C2B C3B C4B -55.4(11) . . . . ? C2B C3B C4B C11B 44.7(11) . . . . ? C12B C5B C6B C7B 6.1(10) . . . . ? C5B C6B C7B C8B -8.4(12) . . . . ? C6B C7B C8B C13B 4.8(14) . . . . ? C13B N9B C10B C11B -1.9(18) . . . . ? C14 N9B C10B C11B 174.5(17) . . . . ? C13B N9B C10B C1B 178.1(13) . . . . ? C14 N9B C10B C1B -6(3) . . . . ? C2B C1B C10B C11B -8.8(17) . . . . ? C2B C1B C10B N9B 171.3(15) . . . . ? N9B C10B C11B C12B 1.1(15) . . . . ? C1B C10B C11B C12B -178.9(12) . . . . ? N9B C10B C11B C4B 179.3(12) . . . . ? C1B C10B C11B C4B -0.6(17) . . . . ? C3B C4B C11B C10B -17.5(13) . . . . ? C3B C4B C11B C12B 160.3(10) . . . . ? C10B C11B C12B C13B 0.1(12) . . . . ? C4B C11B C12B C13B -177.9(10) . . . . ? C10B C11B C12B C5B 179.2(10) . . . . ? C4B C11B C12B C5B 1.2(18) . . . . ? C6B C5B C12B C13B -0.8(12) . . . . ? C6B C5B C12B C11B -179.8(10) . . . . ? C7B C8B C13B C12B 0.5(17) . . . . ? C7B C8B C13B N9B 178.0(15) . . . . ? C11B C12B C13B C8B 176.8(11) . . . . ? C5B C12B C13B C8B -2.5(16) . . . . ? C11B C12B C13B N9B -1.2(14) . . . . ? C5B C12B C13B N9B 179.5(12) . . . . ? C10B N9B C13B C8B -176.0(14) . . . . ? C14 N9B C13B C8B 8(3) . . . . ? C10B N9B C13B C12B 1.9(18) . . . . ? C14 N9B C13B C12B -174.4(18) . . . . ? C10 N9 C14 C15 61(2) . . . . ? C13 N9 C14 C15 -127.5(14) . . . . ? C10 N9 C14 C16 -115.9(15) . . . 3_656 ? C13 N9 C14 C16 55(2) . . . 3_656 ? C10B N9B C14 C16B 127.6(16) . . . 3_656 ? C13B N9B C14 C16B -57(2) . . . 3_656 ? C10B N9B C14 C15B -56(2) . . . . ? C13B N9B C14 C15B 119.7(16) . . . . ? C16 C14 C15 C16 1.6(5) 3_656 . . . ? N9 C14 C15 C16 -175.8(7) . . . . ? C14 C15 C16 C14 -1.6(6) . . . 3_656 ? C16B C14 C15B C16B 2.4(6) 3_656 . . . ? N9B C14 C15B C16B -174.0(7) . . . . ? C14 C15B C16B C14 -2.5(6) . . . 3_656 ?