#------------------------------------------------------------------------------ #$Date: 2024-01-06 09:56:22 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288784 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247601.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_7247601 loop_ _publ_author_name 'Manoharan, Deepak' 'Ahmad, Shamim' 'Tothadi, Srinu' 'Emmerling, Franziska' 'Bhattacharya, Biswajit' 'Ghosh, Soumyajit' _publ_section_title ; Linker size dependent mechanical properties of di-imine based molecular crystals ; _journal_issue 46 _journal_name_full CrystEngComm _journal_page_first 6416 _journal_page_last 6423 _journal_paper_doi 10.1039/D3CE00928A _journal_volume 25 _journal_year 2023 _chemical_formula_moiety 'C30 H44 N2 O2' _chemical_formula_sum 'C30 H44 N2 O2' _chemical_formula_weight 464.67 _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 2022-10-27 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2023-08-01 deposited with the CCDC. 2023-10-31 downloaded from the CCDC. ; _cell_angle_alpha 82.665(10) _cell_angle_beta 87.026(10) _cell_angle_gamma 72.301(9) _cell_formula_units_Z 1 _cell_length_a 6.4470(15) _cell_length_b 10.416(3) _cell_length_c 11.367(3) _cell_measurement_reflns_used 2756 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 26.82 _cell_measurement_theta_min 2.58 _cell_volume 721.2(3) _computing_cell_refinement 'SAINT V8.40B (?, 2016)' _computing_data_reduction 'SAINT V8.40B (?, 2016)' _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 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 298 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker D8 QUEST' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1034 _diffrn_reflns_av_unetI/netI 0.0497 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 24832 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 24.999 _diffrn_reflns_theta_max 24.999 _diffrn_reflns_theta_min 2.580 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_correction_T_min 0.6433 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1066 before and 0.0771 after correction. The Ratio of minimum to maximum transmission is 0.8622. The \l/2 correction factor is Not present.' _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.070 _exptl_crystal_description needle _exptl_crystal_F_000 254 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.261 _refine_diff_density_min -0.177 _refine_diff_density_rms 0.036 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 161 _refine_ls_number_reflns 2550 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.028 _refine_ls_R_factor_all 0.1117 _refine_ls_R_factor_gt 0.0645 _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^)+(0.0565P)^2^+0.4627P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1514 _refine_ls_wR_factor_ref 0.1770 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1545 _reflns_number_total 2550 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00928a3.cif _cod_data_source_block dm_17_0m_a _cod_depositor_comments 'Adding full bibliography for 7247601--7247604.cif.' _cod_original_cell_volume 721.1(3) _cod_database_code 7247601 _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_max 0.997 _shelx_estimated_absorpt_t_min 0.992 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Aromatic/amide H refined with riding coordinates: C4(H4), C6(H6), C15(H15) 2.b Idealised Me refined as rotating group: C1(H1A,H1B,H1C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C14(H14A,H14B,H14C) 2.c Idealised tetrahedral OH refined as rotating group: O1(H1) ; _shelx_res_file ; TITL DM_17_0m_a.res in P-1 dm_17_0m_a.res created by SHELXL-2018/3 at 16:56:55 on 27-Oct-2022 CELL 0.71073 6.447 10.4157 11.3669 82.665 87.026 72.301 ZERR 1 0.0015 0.0026 0.003 0.01 0.01 0.009 LATT 1 SFAC C H N O UNIT 30 44 2 2 L.S. 4 PLAN -4 0 0 SIZE 0.05 0.07 0.12 TEMP 24.85 HTAB BOND $H CONF fmap 2 acta OMIT -3 50 REM REM REM WGHT 0.056500 0.462700 FVAR 1.17234 O1 4 0.740424 0.347984 0.345140 11.00000 0.05105 0.05593 = 0.08002 -0.01760 -0.02290 -0.00263 AFIX 147 H1 2 0.828905 0.360058 0.388472 11.00000 -1.50000 AFIX 0 N1 3 0.924880 0.486196 0.464863 11.00000 0.03961 0.06829 = 0.05420 -0.00771 -0.01504 -0.01682 C1 1 -0.116279 0.834103 0.169456 11.00000 0.06450 0.06375 = 0.12084 -0.00035 -0.04124 -0.00127 AFIX 137 H1A 2 -0.061166 0.802943 0.094752 11.00000 -1.50000 H1B 2 -0.224240 0.921113 0.155813 11.00000 -1.50000 H1C 2 -0.180661 0.770444 0.213277 11.00000 -1.50000 AFIX 0 C2 1 0.069813 0.846502 0.240138 11.00000 0.05645 0.04569 = 0.06288 -0.00622 -0.00742 -0.00767 C3 1 0.243668 0.710622 0.270315 11.00000 0.04227 0.04849 = 0.04551 -0.00581 -0.00587 -0.01351 C4 1 0.414681 0.701326 0.342625 11.00000 0.05200 0.04768 = 0.05560 -0.01077 -0.00907 -0.01774 AFIX 43 H4 2 0.417751 0.778065 0.375440 11.00000 -1.20000 AFIX 0 C5 1 0.580130 0.582881 0.367728 11.00000 0.03918 0.05755 = 0.04526 -0.00945 -0.00897 -0.01605 C6 1 0.755476 0.585800 0.442019 11.00000 0.05502 0.06079 = 0.05503 -0.01295 -0.01108 -0.02200 AFIX 43 H6 2 0.742521 0.665384 0.474653 11.00000 -1.20000 AFIX 0 C7 1 0.175887 0.942521 0.164229 11.00000 0.08861 0.05398 = 0.10971 0.00559 -0.00773 -0.01497 AFIX 137 H7A 2 0.297183 0.949703 0.205654 11.00000 -1.50000 H7B 2 0.071188 1.030575 0.149150 11.00000 -1.50000 H7C 2 0.225764 0.907458 0.090314 11.00000 -1.50000 AFIX 0 C8 1 0.606230 0.293831 0.113593 11.00000 0.08503 0.08589 = 0.07880 -0.04144 0.00856 -0.01777 AFIX 137 H8A 2 0.610790 0.364858 0.051678 11.00000 -1.50000 H8B 2 0.601379 0.215343 0.079108 11.00000 -1.50000 H8C 2 0.733924 0.270895 0.161226 11.00000 -1.50000 AFIX 0 C9 1 0.402534 0.342432 0.191563 11.00000 0.05070 0.05470 = 0.06188 -0.01902 -0.01007 -0.00969 C10 1 0.393792 0.228318 0.289216 11.00000 0.07771 0.05573 = 0.09973 -0.02288 -0.01036 -0.02321 AFIX 137 H10A 2 0.511004 0.212465 0.343226 11.00000 -1.50000 H10B 2 0.407564 0.146920 0.254220 11.00000 -1.50000 H10C 2 0.257327 0.254036 0.331416 11.00000 -1.50000 AFIX 0 C11 1 0.202879 0.371062 0.114044 11.00000 0.08331 0.07571 = 0.09445 -0.03537 -0.03573 -0.01966 AFIX 137 H11A 2 0.073023 0.402243 0.160817 11.00000 -1.50000 H11B 2 0.203590 0.289380 0.083083 11.00000 -1.50000 H11C 2 0.206708 0.439532 0.049576 11.00000 -1.50000 AFIX 0 C12 1 0.407668 0.468398 0.246388 11.00000 0.04032 0.04842 = 0.04496 -0.00982 -0.00858 -0.01154 C13 1 0.578835 0.465547 0.320207 11.00000 0.03487 0.04439 = 0.05148 -0.00425 -0.00798 -0.00348 C14 1 -0.024465 0.907888 0.353433 11.00000 0.09687 0.08365 = 0.09177 -0.02575 -0.00248 0.01622 AFIX 137 H14A 2 -0.088269 0.847004 0.401985 11.00000 -1.50000 H14B 2 -0.133980 0.993048 0.333353 11.00000 -1.50000 H14C 2 0.089553 0.922223 0.396225 11.00000 -1.50000 AFIX 0 C15 1 0.247412 0.591754 0.224416 11.00000 0.03911 0.05074 = 0.04591 -0.00788 -0.01030 -0.01235 AFIX 43 H15 2 0.133876 0.595737 0.175473 11.00000 -1.20000 AFIX 0 HKLF 4 REM DM_17_0m_a.res in P-1 REM wR2 = 0.1770, GooF = S = 1.028, Restrained GooF = 1.028 for all data REM R1 = 0.0645 for 1545 Fo > 4sig(Fo) and 0.1117 for all 2550 data REM 161 parameters refined using 0 restraints END WGHT 0.0562 0.4633 REM Instructions for potential hydrogen bonds HTAB O1 N1 REM Highest difference peak 0.261, deepest hole -0.177, 1-sigma level 0.036 Q1 1 0.5292 0.7304 0.3917 11.00000 0.05 0.26 Q2 1 0.8503 0.4168 0.4171 11.00000 0.05 0.17 Q3 1 0.6332 0.7131 0.5007 11.00000 0.05 0.14 Q4 1 0.4723 0.6186 0.3743 11.00000 0.05 0.13 ; _shelx_res_checksum 48638 _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 O1 O 0.7404(3) 0.3480(2) 0.3451(2) 0.0637(6) Uani 1 1 d . . . . . H1 H 0.828905 0.360058 0.388472 0.096 Uiso 1 1 calc GR . . . . N1 N 0.9249(4) 0.4862(3) 0.4649(2) 0.0533(7) Uani 1 1 d . . . . . C1 C -0.1163(6) 0.8341(4) 0.1695(4) 0.0866(12) Uani 1 1 d . . . . . H1A H -0.061166 0.802943 0.094752 0.130 Uiso 1 1 calc GR . . . . H1B H -0.224240 0.921113 0.155813 0.130 Uiso 1 1 calc GR . . . . H1C H -0.180661 0.770444 0.213277 0.130 Uiso 1 1 calc GR . . . . C2 C 0.0698(5) 0.8465(3) 0.2401(3) 0.0565(8) Uani 1 1 d . . . . . C3 C 0.2437(4) 0.7106(3) 0.2703(2) 0.0452(7) Uani 1 1 d . . . . . C4 C 0.4147(4) 0.7013(3) 0.3426(3) 0.0504(7) Uani 1 1 d . . . . . H4 H 0.417751 0.778065 0.375440 0.060 Uiso 1 1 calc R . . . . C5 C 0.5801(4) 0.5829(3) 0.3677(2) 0.0464(7) Uani 1 1 d . . . . . C6 C 0.7555(5) 0.5858(3) 0.4420(3) 0.0550(8) Uani 1 1 d . . . . . H6 H 0.742521 0.665384 0.474653 0.066 Uiso 1 1 calc R . . . . C7 C 0.1759(6) 0.9425(3) 0.1642(4) 0.0867(12) Uani 1 1 d . . . . . H7A H 0.297183 0.949703 0.205654 0.130 Uiso 1 1 calc GR . . . . H7B H 0.071188 1.030575 0.149150 0.130 Uiso 1 1 calc GR . . . . H7C H 0.225764 0.907458 0.090314 0.130 Uiso 1 1 calc GR . . . . C8 C 0.6062(6) 0.2938(4) 0.1136(3) 0.0825(11) Uani 1 1 d . . . . . H8A H 0.610790 0.364858 0.051678 0.124 Uiso 1 1 calc GR . . . . H8B H 0.601379 0.215343 0.079108 0.124 Uiso 1 1 calc GR . . . . H8C H 0.733924 0.270895 0.161226 0.124 Uiso 1 1 calc GR . . . . C9 C 0.4025(5) 0.3424(3) 0.1916(3) 0.0557(8) Uani 1 1 d . . . . . C10 C 0.3938(6) 0.2283(3) 0.2892(3) 0.0754(11) Uani 1 1 d . . . . . H10A H 0.511004 0.212465 0.343226 0.113 Uiso 1 1 calc GR . . . . H10B H 0.407564 0.146920 0.254220 0.113 Uiso 1 1 calc GR . . . . H10C H 0.257327 0.254036 0.331416 0.113 Uiso 1 1 calc GR . . . . C11 C 0.2029(6) 0.3711(4) 0.1140(3) 0.0819(12) Uani 1 1 d . . . . . H11A H 0.073023 0.402243 0.160817 0.123 Uiso 1 1 calc GR . . . . H11B H 0.203590 0.289380 0.083083 0.123 Uiso 1 1 calc GR . . . . H11C H 0.206708 0.439532 0.049576 0.123 Uiso 1 1 calc GR . . . . C12 C 0.4077(4) 0.4684(3) 0.2464(2) 0.0443(7) Uani 1 1 d . . . . . C13 C 0.5788(4) 0.4655(3) 0.3202(2) 0.0453(7) Uani 1 1 d . . . . . C14 C -0.0245(7) 0.9079(4) 0.3534(4) 0.0991(14) Uani 1 1 d . . . . . H14A H -0.088269 0.847004 0.401985 0.149 Uiso 1 1 calc GR . . . . H14B H -0.133980 0.993048 0.333353 0.149 Uiso 1 1 calc GR . . . . H14C H 0.089553 0.922223 0.396225 0.149 Uiso 1 1 calc GR . . . . C15 C 0.2474(4) 0.5918(3) 0.2244(2) 0.0450(7) Uani 1 1 d . . . . . H15 H 0.133876 0.595737 0.175473 0.054 Uiso 1 1 calc R . . . . 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 0.0510(13) 0.0559(13) 0.0800(17) -0.0176(11) -0.0229(11) -0.0026(11) N1 0.0396(13) 0.0683(17) 0.0542(16) -0.0077(13) -0.0150(11) -0.0168(13) C1 0.065(2) 0.064(2) 0.121(3) 0.000(2) -0.041(2) -0.0013(18) C2 0.0565(19) 0.0457(17) 0.063(2) -0.0062(15) -0.0074(15) -0.0077(15) C3 0.0423(15) 0.0485(17) 0.0455(17) -0.0058(13) -0.0059(13) -0.0135(13) C4 0.0520(17) 0.0477(17) 0.0556(19) -0.0108(14) -0.0091(14) -0.0177(14) C5 0.0392(15) 0.0576(18) 0.0453(17) -0.0095(14) -0.0090(12) -0.0160(14) C6 0.0550(18) 0.061(2) 0.0550(19) -0.0130(15) -0.0111(15) -0.0220(16) C7 0.089(3) 0.054(2) 0.110(3) 0.006(2) -0.008(2) -0.015(2) C8 0.085(3) 0.086(3) 0.079(3) -0.041(2) 0.009(2) -0.018(2) C9 0.0507(18) 0.0547(19) 0.062(2) -0.0190(16) -0.0101(15) -0.0097(15) C10 0.078(2) 0.056(2) 0.100(3) -0.023(2) -0.010(2) -0.0232(18) C11 0.083(2) 0.076(2) 0.094(3) -0.035(2) -0.036(2) -0.020(2) C12 0.0403(15) 0.0484(17) 0.0450(17) -0.0098(13) -0.0086(13) -0.0115(13) C13 0.0349(14) 0.0444(16) 0.0515(18) -0.0042(13) -0.0080(13) -0.0035(13) C14 0.097(3) 0.084(3) 0.092(3) -0.026(2) -0.002(2) 0.016(2) C15 0.0391(15) 0.0507(17) 0.0459(17) -0.0079(13) -0.0103(12) -0.0124(13) 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 C13 O1 H1 109.5 . . ? C6 N1 N1 113.8(3) . 2_766 ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? C1 C2 C3 112.6(3) . . ? C1 C2 C7 107.7(3) . . ? C1 C2 C14 108.5(3) . . ? C3 C2 C7 108.4(3) . . ? C3 C2 C14 110.2(3) . . ? C14 C2 C7 109.3(3) . . ? C4 C3 C2 120.2(3) . . ? C4 C3 C15 116.1(3) . . ? C15 C3 C2 123.6(2) . . ? C3 C4 H4 118.8 . . ? C5 C4 C3 122.3(3) . . ? C5 C4 H4 118.8 . . ? C4 C5 C6 117.6(3) . . ? C4 C5 C13 120.0(2) . . ? C13 C5 C6 122.3(3) . . ? N1 C6 C5 123.8(3) . . ? N1 C6 H6 118.1 . . ? C5 C6 H6 118.1 . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7B 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C9 C8 H8A 109.5 . . ? C9 C8 H8B 109.5 . . ? C9 C8 H8C 109.5 . . ? C10 C9 C8 109.4(3) . . ? C10 C9 C12 110.3(2) . . ? C11 C9 C8 107.9(3) . . ? C11 C9 C10 107.3(3) . . ? C11 C9 C12 112.0(2) . . ? C12 C9 C8 109.9(3) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C9 121.7(2) . . ? C15 C12 C9 122.0(2) . . ? C15 C12 C13 116.4(2) . . ? O1 C13 C5 120.5(2) . . ? O1 C13 C12 119.2(2) . . ? C5 C13 C12 120.3(2) . . ? C2 C14 H14A 109.5 . . ? C2 C14 H14B 109.5 . . ? C2 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C3 C15 H15 117.6 . . ? C12 C15 C3 124.9(2) . . ? C12 C15 H15 117.6 . . ? 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 H1 0.8200 . ? O1 C13 1.353(3) . ? N1 N1 1.403(4) 2_766 ? N1 C6 1.268(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C1 C2 1.524(4) . ? C2 C3 1.526(4) . ? C2 C7 1.532(5) . ? C2 C14 1.526(5) . ? C3 C4 1.382(4) . ? C3 C15 1.397(4) . ? C4 H4 0.9300 . ? C4 C5 1.372(4) . ? C5 C6 1.456(4) . ? C5 C13 1.400(4) . ? C6 H6 0.9300 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C8 C9 1.535(4) . ? C9 C10 1.531(4) . ? C9 C11 1.530(4) . ? C9 C12 1.532(4) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.412(3) . ? C12 C15 1.385(4) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15 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 N1 N1 C6 C5 178.0(3) 2_766 . . . ? C1 C2 C3 C4 -174.5(3) . . . . ? C1 C2 C3 C15 8.4(4) . . . . ? C2 C3 C4 C5 -176.9(3) . . . . ? C2 C3 C15 C12 177.3(3) . . . . ? C3 C4 C5 C6 178.1(3) . . . . ? C3 C4 C5 C13 -0.5(4) . . . . ? C4 C3 C15 C12 0.0(4) . . . . ? C4 C5 C6 N1 -174.9(3) . . . . ? C4 C5 C13 O1 -179.5(3) . . . . ? C4 C5 C13 C12 0.0(4) . . . . ? C6 C5 C13 O1 2.0(4) . . . . ? C6 C5 C13 C12 -178.6(3) . . . . ? C7 C2 C3 C4 66.4(4) . . . . ? C7 C2 C3 C15 -110.7(3) . . . . ? C8 C9 C12 C13 -59.4(4) . . . . ? C8 C9 C12 C15 119.3(3) . . . . ? C9 C12 C13 O1 -1.3(4) . . . . ? C9 C12 C13 C5 179.2(3) . . . . ? C9 C12 C15 C3 -179.2(3) . . . . ? C10 C9 C12 C13 61.3(4) . . . . ? C10 C9 C12 C15 -120.0(3) . . . . ? C11 C9 C12 C13 -179.3(3) . . . . ? C11 C9 C12 C15 -0.7(4) . . . . ? C13 C5 C6 N1 3.7(5) . . . . ? C13 C12 C15 C3 -0.5(4) . . . . ? C14 C2 C3 C4 -53.2(4) . . . . ? C14 C2 C3 C15 129.7(3) . . . . ? C15 C3 C4 C5 0.4(4) . . . . ? C15 C12 C13 O1 180.0(3) . . . . ? C15 C12 C13 C5 0.5(4) . . . . ?