#------------------------------------------------------------------------------ #$Date: 2020-10-06 14:39:24 +0300 (Tue, 06 Oct 2020) $ #$Revision: 258087 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/99/7239975.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_7239975 loop_ _publ_author_name 'Barry, Kristy-Lyn' 'Grimmer, Craig D.' 'Munro, Orde Q.' 'Akerman, Matthew P.' _publ_section_title ; Self-assembled supramolecular structures of O,N,N′ tridentate imidazole--phenol Schiff base compounds ; _journal_issue 13 _journal_name_full 'RSC Advances' _journal_page_first 7867 _journal_page_last 7878 _journal_paper_doi 10.1039/C9RA10488G _journal_volume 10 _journal_year 2020 _chemical_formula_moiety 'C15 H19 N3 O' _chemical_formula_sum 'C15 H19 N3 O' _chemical_formula_weight 257.33 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-01-15 deposited with the CCDC. 2020-02-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 104.478(3) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 36.239(6) _cell_length_b 7.1570(12) _cell_length_c 11.2151(19) _cell_measurement_reflns_used 2952 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 28.2 _cell_measurement_theta_min 1.2 _cell_volume 2816.4(8) _computing_cell_refinement 'SAINT-Plus (Bruker, 2012)' _computing_data_collection 'APEX2 (Bruker, 2012)' _computing_data_reduction 'SAINT-Plus (Bruker, 2012)' _computing_molecular_graphics 'WinGX (Farrugia, 2012)' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXL-2016/6 (Sheldrick, 2016)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method '\w and \f-scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'Incoatec microsource' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0411 _diffrn_reflns_av_unetI/netI 0.0229 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_limit_h_max 48 _diffrn_reflns_limit_h_min -48 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 29656 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.227 _diffrn_reflns_theta_min 1.161 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.6835 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker 2012' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.214 _exptl_crystal_description planar _exptl_crystal_F_000 1104 _exptl_crystal_size_max 0.410 _exptl_crystal_size_mid 0.230 _exptl_crystal_size_min 0.090 _refine_diff_density_max 0.396 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.052 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 180 _refine_ls_number_reflns 3453 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.113 _refine_ls_R_factor_all 0.0616 _refine_ls_R_factor_gt 0.0529 _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^)+(0.0473P)^2^+5.2899P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1344 _refine_ls_wR_factor_ref 0.1395 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2952 _reflns_number_total 3453 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9ra10488g2.cif _cod_data_source_block shelx _cod_depositor_comments 'Adding full bibliography for 7239975--7239978.cif.' _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 7239975 _shelx_shelxl_version_number 2014/7 _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 0.969 _shelx_estimated_absorpt_t_max 0.993 _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL mo_MA_KLB_TEACA_0m in C2/c CELL 0.71073 36.2386 7.1570 11.2151 90.000 104.478 90.000 ZERR 8.00 0.0060 0.0012 0.0019 0.000 0.003 0.000 LATT 7 SYMM - X, Y, 1/2 - Z SFAC C H N O UNIT 120 152 24 8 MERG 3 OMIT 0 6 0 OMIT 9 3 3 OMIT -6 6 3 OMIT 0 6 3 OMIT -18 0 6 FMAP 2 PLAN 5 SIZE 0.090 0.230 0.410 ACTA BOND $H CONF L.S. 4 TEMP -173.00 WGHT 0.047300 5.289899 FVAR 0.08063 O1 4 0.284826 0.363205 0.420459 11.00000 0.01741 0.02603 = 0.01689 0.00250 0.00509 0.00135 N2 3 0.329684 0.190475 0.891625 11.00000 0.02131 0.01415 = 0.01476 0.00008 0.00446 0.00122 N3 3 0.344327 0.257409 0.641217 11.00000 0.02163 0.01508 = 0.01559 -0.00075 0.00568 0.00019 N1 3 0.269730 0.138494 0.789167 11.00000 0.02102 0.01953 = 0.01618 0.00117 0.00606 0.00034 C3 1 0.370417 0.232777 0.922195 11.00000 0.02013 0.02161 = 0.01820 0.00047 0.00282 0.00067 AFIX 137 H3A 2 0.378761 0.248730 0.846167 11.00000 -1.50000 H3B 2 0.384601 0.129755 0.970315 11.00000 -1.50000 H3C 2 0.375208 0.348217 0.970606 11.00000 -1.50000 AFIX 0 C4 1 0.304544 0.187229 0.778820 11.00000 0.01838 0.01492 = 0.01607 -0.00155 0.00445 0.00098 C5 1 0.311207 0.224081 0.658221 11.00000 0.02132 0.01673 = 0.01454 -0.00130 0.00396 -0.00086 AFIX 43 H5 2 0.289958 0.223427 0.588561 11.00000 -1.20000 AFIX 0 C6 1 0.349362 0.281946 0.520558 11.00000 0.02127 0.01200 = 0.01562 -0.00072 0.00665 -0.00210 C11 1 0.387207 0.260792 0.511193 11.00000 0.01888 0.01320 = 0.01836 -0.00011 0.00287 -0.00062 AFIX 43 H11 2 0.406523 0.237249 0.584220 11.00000 -1.20000 AFIX 0 C10 1 0.397671 0.272749 0.399896 11.00000 0.01749 0.01460 = 0.02207 -0.00192 0.00676 -0.00081 C12 1 0.439075 0.255328 0.389788 11.00000 0.01866 0.02556 = 0.02652 -0.00056 0.00979 -0.00034 C15 1 0.466455 0.208482 0.514236 11.00000 0.01858 0.05324 = 0.03098 -0.00323 0.00599 0.00444 AFIX 137 H15C 2 0.492519 0.199949 0.504366 11.00000 -1.50000 H15B 2 0.459171 0.088691 0.544023 11.00000 -1.50000 H15A 2 0.465169 0.306873 0.573836 11.00000 -1.50000 AFIX 0 C13 1 0.442228 0.099014 0.298229 11.00000 0.02748 0.04733 = 0.03695 -0.01143 0.01421 0.00457 AFIX 137 H13A 2 0.468682 0.089349 0.292256 11.00000 -1.50000 H13B 2 0.425680 0.128387 0.217009 11.00000 -1.50000 H13C 2 0.434325 -0.020040 0.327232 11.00000 -1.50000 AFIX 0 C9 1 0.368411 0.308639 0.294743 11.00000 0.02277 0.01986 = 0.01593 0.00026 0.00716 -0.00223 AFIX 43 H9 2 0.374304 0.314877 0.216923 11.00000 -1.20000 AFIX 0 C8 1 0.331109 0.335320 0.300911 11.00000 0.02042 0.01923 = 0.01614 0.00094 0.00315 -0.00119 AFIX 43 H8 2 0.312071 0.360457 0.227477 11.00000 -1.20000 AFIX 0 C7 1 0.320836 0.326037 0.413172 11.00000 0.01825 0.01271 = 0.01919 -0.00001 0.00561 -0.00241 C2 1 0.309721 0.142578 0.976303 11.00000 0.02732 0.01707 = 0.01481 0.00145 0.00765 0.00142 AFIX 43 H2 2 0.319617 0.133310 1.062922 11.00000 -1.20000 AFIX 0 C1 1 0.272994 0.110854 0.912406 11.00000 0.02614 0.01756 = 0.01779 0.00183 0.00956 0.00167 AFIX 43 H1 2 0.252807 0.075160 0.947746 11.00000 -1.20000 AFIX 0 C14 1 0.451457 0.441534 0.344058 11.00000 0.02596 0.04195 = 0.06317 0.01414 0.01954 -0.00454 AFIX 137 H14B 2 0.449820 0.540794 0.402710 11.00000 -1.50000 H14C 2 0.434673 0.471562 0.263336 11.00000 -1.50000 H14A 2 0.477786 0.431145 0.336928 11.00000 -1.50000 AFIX 0 H101 2 0.267487 0.357033 0.337644 11.00000 0.06463 HKLF 4 1.0 1.00 0.00 0.00 0.00 1.00 0.00 0.00 0.00 1.00 REM mo_MA_KLB_TEACA_0m in C2/c REM R1 = 0.0529 for 2952 Fo > 4sig(Fo) and 0.0616 for all 3453 data REM 180 parameters refined using 0 restraints END WGHT 0.0473 5.2899 REM Highest difference peak 0.396, deepest hole -0.249, 1-sigma level 0.052 Q1 1 0.4181 0.2768 0.3992 11.00000 0.05 0.40 Q2 1 0.3682 0.2834 0.5193 11.00000 0.05 0.35 Q3 1 0.3496 0.3073 0.3064 11.00000 0.05 0.33 Q4 1 0.3362 0.3311 0.4723 11.00000 0.05 0.32 Q5 1 0.3276 0.3309 0.3606 11.00000 0.05 0.32 ; _shelx_res_checksum 46071 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -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 O1 O 0.28483(3) 0.36320(17) 0.42046(10) 0.0200(3) Uani 1 1 d . . . . . N2 N 0.32968(4) 0.19048(19) 0.89163(12) 0.0168(3) Uani 1 1 d . . . . . N3 N 0.34433(4) 0.25741(19) 0.64122(12) 0.0172(3) Uani 1 1 d . . . . . N1 N 0.26973(4) 0.1385(2) 0.78917(12) 0.0187(3) Uani 1 1 d . . . . . C3 C 0.37042(5) 0.2328(2) 0.92219(15) 0.0203(3) Uani 1 1 d . . . . . H3A H 0.3788 0.2487 0.8462 0.030 Uiso 1 1 calc R U . . . H3B H 0.3846 0.1298 0.9703 0.030 Uiso 1 1 calc R U . . . H3C H 0.3752 0.3482 0.9706 0.030 Uiso 1 1 calc R U . . . C4 C 0.30454(4) 0.1872(2) 0.77882(14) 0.0164(3) Uani 1 1 d . . . . . C5 C 0.31121(4) 0.2241(2) 0.65822(14) 0.0176(3) Uani 1 1 d . . . . . H5 H 0.2900 0.2234 0.5886 0.021 Uiso 1 1 calc R U . . . C6 C 0.34936(4) 0.2819(2) 0.52056(14) 0.0159(3) Uani 1 1 d . . . . . C11 C 0.38721(4) 0.2608(2) 0.51119(14) 0.0171(3) Uani 1 1 d . . . . . H11 H 0.4065 0.2372 0.5842 0.021 Uiso 1 1 calc R U . . . C10 C 0.39767(4) 0.2727(2) 0.39990(15) 0.0177(3) Uani 1 1 d . . . . . C12 C 0.43908(5) 0.2553(2) 0.38979(16) 0.0228(4) Uani 1 1 d . . . . . C15 C 0.46645(5) 0.2085(3) 0.51424(18) 0.0343(5) Uani 1 1 d . . . . . H15C H 0.4925 0.1999 0.5044 0.051 Uiso 1 1 calc R U . . . H15B H 0.4592 0.0887 0.5440 0.051 Uiso 1 1 calc R U . . . H15A H 0.4652 0.3069 0.5738 0.051 Uiso 1 1 calc R U . . . C13 C 0.44223(6) 0.0990(3) 0.29823(19) 0.0362(5) Uani 1 1 d . . . . . H13A H 0.4687 0.0893 0.2923 0.054 Uiso 1 1 calc R U . . . H13B H 0.4257 0.1284 0.2170 0.054 Uiso 1 1 calc R U . . . H13C H 0.4343 -0.0200 0.3272 0.054 Uiso 1 1 calc R U . . . C9 C 0.36841(5) 0.3086(2) 0.29474(14) 0.0191(3) Uani 1 1 d . . . . . H9 H 0.3743 0.3149 0.2169 0.023 Uiso 1 1 calc R U . . . C8 C 0.33111(5) 0.3353(2) 0.30091(14) 0.0188(3) Uani 1 1 d . . . . . H8 H 0.3121 0.3605 0.2275 0.023 Uiso 1 1 calc R U . . . C7 C 0.32084(4) 0.3260(2) 0.41317(14) 0.0165(3) Uani 1 1 d . . . . . C2 C 0.30972(5) 0.1426(2) 0.97630(14) 0.0193(3) Uani 1 1 d . . . . . H2 H 0.3196 0.1333 1.0629 0.023 Uiso 1 1 calc R U . . . C1 C 0.27299(5) 0.1109(2) 0.91241(15) 0.0198(3) Uani 1 1 d . . . . . H1 H 0.2528 0.0752 0.9477 0.024 Uiso 1 1 calc R U . . . C14 C 0.45146(6) 0.4415(3) 0.3441(2) 0.0422(5) Uani 1 1 d . . . . . H14B H 0.4498 0.5408 0.4027 0.063 Uiso 1 1 calc R U . . . H14C H 0.4347 0.4716 0.2633 0.063 Uiso 1 1 calc R U . . . H14A H 0.4778 0.4311 0.3369 0.063 Uiso 1 1 calc R U . . . H101 H 0.2675(8) 0.357(4) 0.338(3) 0.065(9) Uiso 1 1 d . . . . . 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 0.0174(5) 0.0260(6) 0.0169(5) 0.0025(5) 0.0051(4) 0.0013(5) N2 0.0213(7) 0.0142(6) 0.0148(6) 0.0001(5) 0.0045(5) 0.0012(5) N3 0.0216(7) 0.0151(6) 0.0156(6) -0.0008(5) 0.0057(5) 0.0002(5) N1 0.0210(7) 0.0195(7) 0.0162(6) 0.0012(5) 0.0061(5) 0.0003(5) C3 0.0201(8) 0.0216(8) 0.0182(7) 0.0005(6) 0.0028(6) 0.0007(6) C4 0.0184(7) 0.0149(7) 0.0161(7) -0.0016(6) 0.0044(5) 0.0010(6) C5 0.0213(7) 0.0167(7) 0.0145(7) -0.0013(6) 0.0040(6) -0.0009(6) C6 0.0213(7) 0.0120(7) 0.0156(7) -0.0007(5) 0.0067(6) -0.0021(5) C11 0.0189(7) 0.0132(7) 0.0184(7) -0.0001(6) 0.0029(6) -0.0006(5) C10 0.0175(7) 0.0146(7) 0.0221(8) -0.0019(6) 0.0068(6) -0.0008(6) C12 0.0187(8) 0.0256(9) 0.0265(8) -0.0006(7) 0.0098(6) -0.0003(6) C15 0.0186(8) 0.0532(13) 0.0310(10) -0.0032(9) 0.0060(7) 0.0044(8) C13 0.0275(9) 0.0473(13) 0.0370(11) -0.0114(9) 0.0142(8) 0.0046(9) C9 0.0228(8) 0.0199(8) 0.0159(7) 0.0003(6) 0.0072(6) -0.0022(6) C8 0.0204(7) 0.0192(8) 0.0161(7) 0.0009(6) 0.0032(6) -0.0012(6) C7 0.0183(7) 0.0127(7) 0.0192(7) 0.0000(6) 0.0056(6) -0.0024(5) C2 0.0273(8) 0.0171(8) 0.0148(7) 0.0015(6) 0.0077(6) 0.0014(6) C1 0.0261(8) 0.0176(8) 0.0178(7) 0.0018(6) 0.0096(6) 0.0017(6) C14 0.0260(10) 0.0420(13) 0.0632(15) 0.0141(11) 0.0195(10) -0.0045(9) 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 C7 O1 H101 109.4(16) . . ? C4 N2 C2 107.00(13) . . ? C4 N2 C3 128.57(13) . . ? C2 N2 C3 124.43(13) . . ? C5 N3 C6 120.79(13) . . ? C4 N1 C1 106.17(13) . . ? N2 C3 H3A 109.5 . . ? N2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? N2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? N1 C4 N2 110.44(13) . . ? N1 C4 C5 120.35(14) . . ? N2 C4 C5 129.20(14) . . ? N3 C5 C4 123.36(14) . . ? N3 C5 H5 118.3 . . ? C4 C5 H5 118.3 . . ? C11 C6 C7 118.60(14) . . ? C11 C6 N3 114.63(13) . . ? C7 C6 N3 126.77(14) . . ? C10 C11 C6 123.18(14) . . ? C10 C11 H11 118.4 . . ? C6 C11 H11 118.4 . . ? C11 C10 C9 116.58(14) . . ? C11 C10 C12 123.33(14) . . ? C9 C10 C12 120.05(14) . . ? C15 C12 C14 108.50(16) . . ? C15 C12 C10 111.83(14) . . ? C14 C12 C10 109.05(14) . . ? C15 C12 C13 107.98(16) . . ? C14 C12 C13 109.33(16) . . ? C10 C12 C13 110.12(14) . . ? C12 C15 H15C 109.5 . . ? C12 C15 H15B 109.5 . . ? H15C C15 H15B 109.5 . . ? C12 C15 H15A 109.5 . . ? H15C C15 H15A 109.5 . . ? H15B C15 H15A 109.5 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C8 C9 C10 121.83(15) . . ? C8 C9 H9 119.1 . . ? C10 C9 H9 119.1 . . ? C9 C8 C7 121.38(14) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? O1 C7 C8 121.44(14) . . ? O1 C7 C6 120.21(14) . . ? C8 C7 C6 118.33(14) . . ? C1 C2 N2 106.97(14) . . ? C1 C2 H2 126.5 . . ? N2 C2 H2 126.5 . . ? C2 C1 N1 109.42(14) . . ? C2 C1 H1 125.3 . . ? N1 C1 H1 125.3 . . ? C12 C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C14 H14A 109.5 . . ? H14B C14 H14A 109.5 . . ? H14C C14 H14A 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 C7 1.3541(19) . ? O1 H101 0.98(3) . ? N2 C4 1.3619(19) . ? N2 C2 1.373(2) . ? N2 C3 1.461(2) . ? N3 C5 1.284(2) . ? N3 C6 1.4208(19) . ? N1 C4 1.342(2) . ? N1 C1 1.372(2) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 C5 1.456(2) . ? C5 H5 0.9500 . ? C6 C11 1.410(2) . ? C6 C7 1.413(2) . ? C11 C10 1.395(2) . ? C11 H11 0.9500 . ? C10 C9 1.399(2) . ? C10 C12 1.538(2) . ? C12 C15 1.534(3) . ? C12 C14 1.535(3) . ? C12 C13 1.542(3) . ? C15 H15C 0.9800 . ? C15 H15B 0.9800 . ? C15 H15A 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C9 C8 1.384(2) . ? C9 H9 0.9500 . ? C8 C7 1.401(2) . ? C8 H8 0.9500 . ? C2 C1 1.364(2) . ? C2 H2 0.9500 . ? C1 H1 0.9500 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C14 H14A 0.9800 . ? 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 C1 N1 C4 N2 0.23(18) . . . . ? C1 N1 C4 C5 178.98(14) . . . . ? C2 N2 C4 N1 -0.29(18) . . . . ? C3 N2 C4 N1 178.83(15) . . . . ? C2 N2 C4 C5 -178.90(16) . . . . ? C3 N2 C4 C5 0.2(3) . . . . ? C6 N3 C5 C4 176.41(14) . . . . ? N1 C4 C5 N3 -174.57(15) . . . . ? N2 C4 C5 N3 3.9(3) . . . . ? C5 N3 C6 C11 -161.59(15) . . . . ? C5 N3 C6 C7 19.1(2) . . . . ? C7 C6 C11 C10 -3.1(2) . . . . ? N3 C6 C11 C10 177.57(14) . . . . ? C6 C11 C10 C9 0.4(2) . . . . ? C6 C11 C10 C12 178.20(15) . . . . ? C11 C10 C12 C15 4.4(2) . . . . ? C9 C10 C12 C15 -177.79(16) . . . . ? C11 C10 C12 C14 -115.54(19) . . . . ? C9 C10 C12 C14 62.2(2) . . . . ? C11 C10 C12 C13 124.50(18) . . . . ? C9 C10 C12 C13 -57.7(2) . . . . ? C11 C10 C9 C8 1.5(2) . . . . ? C12 C10 C9 C8 -176.44(15) . . . . ? C10 C9 C8 C7 -0.5(3) . . . . ? C9 C8 C7 O1 175.96(15) . . . . ? C9 C8 C7 C6 -2.2(2) . . . . ? C11 C6 C7 O1 -174.31(14) . . . . ? N3 C6 C7 O1 5.0(2) . . . . ? C11 C6 C7 C8 3.9(2) . . . . ? N3 C6 C7 C8 -176.83(15) . . . . ? C4 N2 C2 C1 0.22(18) . . . . ? C3 N2 C2 C1 -178.94(14) . . . . ? N2 C2 C1 N1 -0.09(19) . . . . ? C4 N1 C1 C2 -0.09(18) . . . . ?