#------------------------------------------------------------------------------ #$Date: 2020-05-18 06:04:34 +0300 (Mon, 18 May 2020) $ #$Revision: 252127 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/75/7157505.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_7157505 loop_ _publ_author_name 'Yang, Huiyong' 'Xu, Jun' 'Zhang, Yilan' 'He, Lei' 'Zhang, Peng-Fei' 'Li, Wanmei' _publ_section_title ; Synthesis of quinazoin-4-ones through acid ion exchange resin mediated cascade reaction ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D0OB00881H _journal_year 2020 _chemical_formula_moiety 'C16 H14 N2 O2' _chemical_formula_sum 'C16 H14 N2 O2' _chemical_formula_weight 266.29 _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 mixed _atom_sites_solution_primary dual _audit_creation_date 2019-01-04 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-10-16 deposited with the CCDC. 2020-05-17 downloaded from the CCDC. ; _cell_angle_alpha 112.6230(10) _cell_angle_beta 99.490(2) _cell_angle_gamma 94.354(2) _cell_formula_units_Z 2 _cell_length_a 4.9529(7) _cell_length_b 11.1696(16) _cell_length_c 13.2334(19) _cell_measurement_reflns_used 1994 _cell_measurement_temperature 296.15 _cell_measurement_theta_max 26.971 _cell_measurement_theta_min 3.108 _cell_volume 658.67(16) _computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)' _computing_data_reduction 'SAINT v8.34A (Bruker, 2013)' _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 (Sheldrick, 2015)' _diffrn_ambient_temperature 296.15 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.907 _diffrn_measurement_device_type 'Bruker D8 Venture' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0150 _diffrn_reflns_av_unetI/netI 0.0256 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.907 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 5331 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.907 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.744 _diffrn_reflns_theta_min 1.705 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6941 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.0404 before and 0.0274 after correction. The Ratio of minimum to maximum transmission is 0.9309. The \l/2 correction factor is 0.00150.' _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.343 _exptl_crystal_description block _exptl_crystal_F_000 280 _refine_diff_density_max 0.137 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.034 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 181 _refine_ls_number_reflns 2834 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.064 _refine_ls_R_factor_all 0.0702 _refine_ls_R_factor_gt 0.0452 _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^)+(0.0610P)^2^+0.0689P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1149 _refine_ls_wR_factor_ref 0.1277 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1970 _reflns_number_total 2834 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00881h2.cif _cod_data_source_block 190103xj_0m _cod_database_code 7157505 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All O(H) groups 2.a Riding coordinates: O2(H2) 2.b Secondary CH2 refined with riding coordinates: C15(H15A,H15B), C16(H16A,H16B) 2.c Aromatic/amide H refined with riding coordinates: C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14) ; _shelx_res_file ; TITL 190103xj_0P -1 R = 0.05 190103xj_0m.res created by SHELXL-2018/3 at 11:30:21 on 04-Jan-2019 CELL 0.71073 4.9529 11.1696 13.2334 112.623 99.49 94.354 ZERR 2 0.0007 0.0016 0.0019 0.001 0.002 0.002 LATT 1 SFAC C H N O UNIT 32 28 4 4 L.S. 5 PLAN -20 TEMP 23 BOND $H CONF fmap 2 acta OMIT 0 -1 1 REM REM REM WGHT 0.061000 0.068900 FVAR 1.12989 O1 4 0.185631 0.975495 0.326229 11.00000 0.06132 0.03562 = 0.06134 0.01228 0.00929 0.01595 O2 4 0.465176 0.802998 0.511086 11.00000 0.06490 0.04980 = 0.06481 0.01292 -0.00253 0.01643 AFIX 3 H2 2 0.581826 0.858038 0.562846 11.00000 -1.50000 AFIX 0 N1 3 0.194370 0.760149 0.292369 11.00000 0.04133 0.03379 = 0.04147 0.01246 0.00660 0.00710 N2 3 0.409789 0.622771 0.153243 11.00000 0.05962 0.03096 = 0.04339 0.01376 0.01376 0.00716 C1 1 0.264438 0.871489 0.273100 11.00000 0.04236 0.03109 = 0.04335 0.01146 -0.00312 0.00526 C2 1 0.269202 0.640334 0.230122 11.00000 0.04317 0.03041 = 0.03723 0.01081 0.00254 0.00350 C3 1 0.499265 0.731023 0.132931 11.00000 0.04762 0.03461 = 0.03707 0.01475 0.00181 0.00263 C4 1 0.432053 0.854949 0.190269 11.00000 0.04286 0.03333 = 0.03924 0.01466 -0.00355 0.00177 C5 1 0.529978 0.961725 0.167842 11.00000 0.06045 0.03667 = 0.05617 0.02154 0.00017 0.00155 AFIX 43 H5 2 0.484405 1.044315 0.205407 11.00000 -1.20000 AFIX 0 C6 1 0.691854 0.943768 0.090888 11.00000 0.06810 0.05013 = 0.06144 0.03306 0.00197 -0.00591 AFIX 43 H6 2 0.758819 1.014680 0.076891 11.00000 -1.20000 AFIX 0 C7 1 0.757918 0.819836 0.032934 11.00000 0.06448 0.06488 = 0.05020 0.02959 0.01031 -0.00154 AFIX 43 H7 2 0.868018 0.808820 -0.019585 11.00000 -1.20000 AFIX 0 C8 1 0.662143 0.714104 0.052629 11.00000 0.06550 0.04637 = 0.04442 0.01911 0.01232 0.00747 AFIX 43 H8 2 0.704985 0.631561 0.012927 11.00000 -1.20000 AFIX 0 C9 1 0.182433 0.522702 0.252322 11.00000 0.05150 0.03370 = 0.04293 0.01426 0.01305 0.00619 C10 1 -0.056275 0.438206 0.189945 11.00000 0.06369 0.04526 = 0.07257 0.02664 -0.00620 -0.00270 AFIX 43 H10 2 -0.171280 0.456434 0.136323 11.00000 -1.20000 AFIX 0 C11 1 -0.126497 0.326005 0.206524 11.00000 0.07184 0.04931 = 0.08754 0.02950 -0.00238 -0.01438 AFIX 43 H11 2 -0.290431 0.270026 0.164728 11.00000 -1.20000 AFIX 0 C12 1 0.041002 0.296466 0.283132 11.00000 0.09041 0.04501 = 0.07012 0.02985 0.01939 -0.00420 AFIX 43 H12 2 -0.006752 0.220345 0.293297 11.00000 -1.20000 AFIX 0 C13 1 0.280110 0.379643 0.345036 11.00000 0.10141 0.07069 = 0.08317 0.05340 -0.00876 -0.00748 AFIX 43 H13 2 0.396110 0.360057 0.397529 11.00000 -1.20000 AFIX 0 C14 1 0.350503 0.493146 0.329901 11.00000 0.07892 0.06210 = 0.07715 0.04350 -0.01552 -0.01522 AFIX 43 H14 2 0.513032 0.549669 0.372724 11.00000 -1.20000 AFIX 0 C15 1 0.042024 0.776128 0.382296 11.00000 0.04239 0.04632 = 0.05360 0.01562 0.01580 0.00896 AFIX 23 H15A 2 -0.026341 0.690186 0.377918 11.00000 -1.20000 H15B 2 -0.116725 0.818851 0.371085 11.00000 -1.20000 AFIX 0 C16 1 0.220275 0.856393 0.497973 11.00000 0.05499 0.05372 = 0.04917 0.01728 0.01896 0.01491 AFIX 23 H16A 2 0.265464 0.946584 0.507334 11.00000 -1.20000 H16B 2 0.119026 0.855929 0.554660 11.00000 -1.20000 AFIX 0 HKLF 4 REM 190103xj_0P -1 R = 0.05 REM wR2 = 0.1277, GooF = S = 1.064, Restrained GooF = 1.064 for all data REM R1 = 0.0452 for 1970 Fo > 4sig(Fo) and 0.0702 for all 2834 data REM 181 parameters refined using 0 restraints END WGHT 0.0610 0.0690 REM Highest difference peak 0.137, deepest hole -0.201, 1-sigma level 0.034 Q1 1 0.0911 0.3863 0.3585 11.00000 0.05 0.14 Q2 1 0.3960 0.9001 0.1594 11.00000 0.05 0.13 Q3 1 0.4652 0.8556 0.4816 11.00000 0.05 0.13 Q4 1 -0.2483 0.4896 0.1806 11.00000 0.05 0.12 Q5 1 0.6515 0.7346 0.1255 11.00000 0.05 0.12 Q6 1 0.2907 0.7068 0.2842 11.00000 0.05 0.12 Q7 1 0.4436 0.8763 0.2563 11.00000 0.05 0.11 Q8 1 0.2102 0.5794 0.2426 11.00000 0.05 0.11 Q9 1 0.1269 0.4538 0.1983 11.00000 0.05 0.11 Q10 1 0.3633 0.5364 0.0927 11.00000 0.05 0.11 Q11 1 0.0154 0.5021 0.2550 11.00000 0.05 0.10 Q12 1 0.5300 0.8011 0.1869 11.00000 0.05 0.10 Q13 1 0.3636 0.5954 0.4240 11.00000 0.05 0.10 Q14 1 -0.3754 0.2996 0.2031 11.00000 0.05 0.10 Q15 1 -0.0614 0.4145 0.0860 11.00000 0.05 0.10 Q16 1 0.6216 0.7610 0.0149 11.00000 0.05 0.10 Q17 1 -0.0877 0.3567 0.2949 11.00000 0.05 0.10 Q18 1 0.4575 0.6764 0.1433 11.00000 0.05 0.10 Q19 1 0.1990 0.5310 0.3425 11.00000 0.05 0.10 Q20 1 0.3054 0.8041 0.5408 11.00000 0.05 0.10 ; _shelx_res_checksum 58764 _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 0.1856(2) 0.97550(10) 0.32623(10) 0.0550(3) Uani 1 1 d . . . . . O2 O 0.4652(3) 0.80300(11) 0.51109(10) 0.0646(4) Uani 1 1 d . . . . . H2 H 0.581826 0.858038 0.562846 0.097 Uiso 1 1 d R . . . . N1 N 0.1944(2) 0.76015(11) 0.29237(10) 0.0399(3) Uani 1 1 d . . . . . N2 N 0.4098(3) 0.62277(11) 0.15324(10) 0.0447(3) Uani 1 1 d . . . . . C1 C 0.2644(3) 0.87149(13) 0.27310(12) 0.0416(4) Uani 1 1 d . . . . . C2 C 0.2692(3) 0.64033(13) 0.23012(12) 0.0387(4) Uani 1 1 d . . . . . C3 C 0.4993(3) 0.73102(13) 0.13293(12) 0.0408(4) Uani 1 1 d . . . . . C4 C 0.4321(3) 0.85495(13) 0.19027(12) 0.0402(4) Uani 1 1 d . . . . . C5 C 0.5300(4) 0.96172(15) 0.16784(14) 0.0521(4) Uani 1 1 d . . . . . H5 H 0.484405 1.044315 0.205407 0.062 Uiso 1 1 calc R . . . . C6 C 0.6919(4) 0.94377(17) 0.09089(15) 0.0589(5) Uani 1 1 d . . . . . H6 H 0.758819 1.014680 0.076891 0.071 Uiso 1 1 calc R . . . . C7 C 0.7579(4) 0.81984(18) 0.03293(14) 0.0587(5) Uani 1 1 d . . . . . H7 H 0.868018 0.808820 -0.019585 0.070 Uiso 1 1 calc R . . . . C8 C 0.6621(4) 0.71410(16) 0.05263(13) 0.0518(4) Uani 1 1 d . . . . . H8 H 0.704985 0.631561 0.012927 0.062 Uiso 1 1 calc R . . . . C9 C 0.1824(3) 0.52270(13) 0.25232(12) 0.0427(4) Uani 1 1 d . . . . . C10 C -0.0563(4) 0.43821(16) 0.18994(16) 0.0628(5) Uani 1 1 d . . . . . H10 H -0.171280 0.456434 0.136323 0.075 Uiso 1 1 calc R . . . . C11 C -0.1265(5) 0.32601(18) 0.20652(19) 0.0727(6) Uani 1 1 d . . . . . H11 H -0.290431 0.270026 0.164728 0.087 Uiso 1 1 calc R . . . . C12 C 0.0410(5) 0.29647(17) 0.28313(16) 0.0670(6) Uani 1 1 d . . . . . H12 H -0.006752 0.220345 0.293297 0.080 Uiso 1 1 calc R . . . . C13 C 0.2801(5) 0.3796(2) 0.34504(19) 0.0828(7) Uani 1 1 d . . . . . H13 H 0.396110 0.360057 0.397529 0.099 Uiso 1 1 calc R . . . . C14 C 0.3505(4) 0.49315(19) 0.32990(17) 0.0734(6) Uani 1 1 d . . . . . H14 H 0.513032 0.549669 0.372724 0.088 Uiso 1 1 calc R . . . . C15 C 0.0420(3) 0.77613(16) 0.38230(13) 0.0480(4) Uani 1 1 d . . . . . H15A H -0.026341 0.690186 0.377918 0.058 Uiso 1 1 calc R . . . . H15B H -0.116725 0.818851 0.371085 0.058 Uiso 1 1 calc R . . . . C16 C 0.2203(4) 0.85639(17) 0.49797(14) 0.0523(4) Uani 1 1 d . . . . . H16A H 0.265464 0.946584 0.507334 0.063 Uiso 1 1 calc R . . . . H16B H 0.119026 0.855929 0.554660 0.063 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 0.0613(8) 0.0356(6) 0.0613(7) 0.0123(5) 0.0093(6) 0.0159(5) O2 0.0649(8) 0.0498(7) 0.0648(8) 0.0129(6) -0.0025(6) 0.0164(6) N1 0.0413(7) 0.0338(6) 0.0415(7) 0.0125(5) 0.0066(6) 0.0071(5) N2 0.0596(9) 0.0310(6) 0.0434(7) 0.0138(5) 0.0138(6) 0.0072(6) C1 0.0424(9) 0.0311(7) 0.0433(8) 0.0115(6) -0.0031(7) 0.0053(6) C2 0.0432(9) 0.0304(7) 0.0372(7) 0.0108(6) 0.0025(7) 0.0035(6) C3 0.0476(9) 0.0346(7) 0.0371(7) 0.0147(6) 0.0018(7) 0.0026(6) C4 0.0429(9) 0.0333(7) 0.0392(8) 0.0147(6) -0.0035(7) 0.0018(6) C5 0.0604(11) 0.0367(8) 0.0562(10) 0.0215(7) 0.0002(8) 0.0016(7) C6 0.0681(13) 0.0501(10) 0.0614(11) 0.0331(9) 0.0020(9) -0.0059(8) C7 0.0645(12) 0.0649(11) 0.0502(10) 0.0296(9) 0.0103(8) -0.0015(9) C8 0.0655(12) 0.0464(9) 0.0444(9) 0.0191(7) 0.0123(8) 0.0075(8) C9 0.0515(10) 0.0337(7) 0.0429(8) 0.0143(6) 0.0131(7) 0.0062(7) C10 0.0637(12) 0.0453(9) 0.0726(12) 0.0266(9) -0.0062(9) -0.0027(8) C11 0.0718(14) 0.0493(10) 0.0875(14) 0.0295(10) -0.0024(11) -0.0144(9) C12 0.0904(15) 0.0450(9) 0.0701(12) 0.0299(9) 0.0194(11) -0.0042(9) C13 0.1014(18) 0.0707(13) 0.0832(15) 0.0534(12) -0.0088(13) -0.0075(12) C14 0.0789(14) 0.0621(11) 0.0771(13) 0.0435(10) -0.0155(11) -0.0152(10) C15 0.0424(9) 0.0463(9) 0.0536(9) 0.0156(7) 0.0158(7) 0.0090(7) C16 0.0550(11) 0.0537(9) 0.0492(9) 0.0173(8) 0.0190(8) 0.0149(8) 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 C16 O2 H2 109.5 . . ? C1 N1 C15 116.90(12) . . ? C2 N1 C1 121.07(13) . . ? C2 N1 C15 122.02(12) . . ? C2 N2 C3 118.13(12) . . ? O1 C1 N1 119.87(15) . . ? O1 C1 C4 124.60(14) . . ? N1 C1 C4 115.53(12) . . ? N1 C2 C9 118.92(13) . . ? N2 C2 N1 124.15(13) . . ? N2 C2 C9 116.93(12) . . ? N2 C3 C4 121.88(14) . . ? N2 C3 C8 118.61(13) . . ? C4 C3 C8 119.51(14) . . ? C3 C4 C1 119.11(13) . . ? C3 C4 C5 119.83(15) . . ? C5 C4 C1 121.05(14) . . ? C4 C5 H5 120.1 . . ? C6 C5 C4 119.78(16) . . ? C6 C5 H5 120.1 . . ? C5 C6 H6 119.7 . . ? C5 C6 C7 120.51(16) . . ? C7 C6 H6 119.7 . . ? C6 C7 H7 119.7 . . ? C8 C7 C6 120.66(17) . . ? C8 C7 H7 119.7 . . ? C3 C8 H8 120.2 . . ? C7 C8 C3 119.69(16) . . ? C7 C8 H8 120.2 . . ? C10 C9 C2 120.55(14) . . ? C14 C9 C2 120.36(14) . . ? C14 C9 C10 118.94(15) . . ? C9 C10 H10 119.9 . . ? C9 C10 C11 120.18(17) . . ? C11 C10 H10 119.9 . . ? C10 C11 H11 119.6 . . ? C12 C11 C10 120.82(18) . . ? C12 C11 H11 119.6 . . ? C11 C12 H12 120.3 . . ? C11 C12 C13 119.35(17) . . ? C13 C12 H12 120.3 . . ? C12 C13 H13 119.9 . . ? C12 C13 C14 120.22(19) . . ? C14 C13 H13 119.9 . . ? C9 C14 C13 120.48(18) . . ? C9 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? N1 C15 H15A 109.1 . . ? N1 C15 H15B 109.1 . . ? N1 C15 C16 112.52(13) . . ? H15A C15 H15B 107.8 . . ? C16 C15 H15A 109.1 . . ? C16 C15 H15B 109.1 . . ? O2 C16 C15 109.69(13) . . ? O2 C16 H16A 109.7 . . ? O2 C16 H16B 109.7 . . ? C15 C16 H16A 109.7 . . ? C15 C16 H16B 109.7 . . ? H16A C16 H16B 108.2 . . ? 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 C1 1.2358(17) . ? O2 H2 0.8201 . ? O2 C16 1.406(2) . ? N1 C1 1.3927(18) . ? N1 C2 1.3910(18) . ? N1 C15 1.473(2) . ? N2 C2 1.2881(19) . ? N2 C3 1.3923(18) . ? C1 C4 1.447(2) . ? C2 C9 1.500(2) . ? C3 C4 1.396(2) . ? C3 C8 1.403(2) . ? C4 C5 1.406(2) . ? C5 H5 0.9300 . ? C5 C6 1.363(3) . ? C6 H6 0.9300 . ? C6 C7 1.395(3) . ? C7 H7 0.9300 . ? C7 C8 1.371(2) . ? C8 H8 0.9300 . ? C9 C10 1.371(2) . ? C9 C14 1.370(2) . ? C10 H10 0.9300 . ? C10 C11 1.382(2) . ? C11 H11 0.9300 . ? C11 C12 1.359(3) . ? C12 H12 0.9300 . ? C12 C13 1.365(3) . ? C13 H13 0.9300 . ? C13 C14 1.386(3) . ? C14 H14 0.9300 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C15 C16 1.518(2) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? 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 O1 C1 C4 C3 -177.68(14) . . . . ? O1 C1 C4 C5 3.0(2) . . . . ? N1 C1 C4 C3 3.00(19) . . . . ? N1 C1 C4 C5 -176.29(13) . . . . ? N1 C2 C9 C10 94.33(19) . . . . ? N1 C2 C9 C14 -90.3(2) . . . . ? N1 C15 C16 O2 -52.84(18) . . . . ? N2 C2 C9 C10 -85.5(2) . . . . ? N2 C2 C9 C14 89.8(2) . . . . ? N2 C3 C4 C1 -0.1(2) . . . . ? N2 C3 C4 C5 179.24(13) . . . . ? N2 C3 C8 C7 -178.55(15) . . . . ? C1 N1 C2 N2 1.4(2) . . . . ? C1 N1 C2 C9 -178.49(12) . . . . ? C1 N1 C15 C16 -70.01(17) . . . . ? C1 C4 C5 C6 178.75(14) . . . . ? C2 N1 C1 O1 176.96(13) . . . . ? C2 N1 C1 C4 -3.69(19) . . . . ? C2 N1 C15 C16 109.12(16) . . . . ? C2 N2 C3 C4 -2.4(2) . . . . ? C2 N2 C3 C8 177.41(14) . . . . ? C2 C9 C10 C11 176.24(17) . . . . ? C2 C9 C14 C13 -175.48(19) . . . . ? C3 N2 C2 N1 1.8(2) . . . . ? C3 N2 C2 C9 -178.34(12) . . . . ? C3 C4 C5 C6 -0.5(2) . . . . ? C4 C3 C8 C7 1.3(2) . . . . ? C4 C5 C6 C7 0.9(3) . . . . ? C5 C6 C7 C8 -0.2(3) . . . . ? C6 C7 C8 C3 -0.9(3) . . . . ? C8 C3 C4 C1 -179.88(13) . . . . ? C8 C3 C4 C5 -0.6(2) . . . . ? C9 C10 C11 C12 -1.1(3) . . . . ? C10 C9 C14 C13 0.0(3) . . . . ? C10 C11 C12 C13 0.6(3) . . . . ? C11 C12 C13 C14 0.1(4) . . . . ? C12 C13 C14 C9 -0.4(4) . . . . ? C14 C9 C10 C11 0.8(3) . . . . ? C15 N1 C1 O1 -3.9(2) . . . . ? C15 N1 C1 C4 175.45(12) . . . . ? C15 N1 C2 N2 -177.72(14) . . . . ? C15 N1 C2 C9 2.4(2) . . . . ?