#------------------------------------------------------------------------------ #$Date: 2020-10-06 11:48:21 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257536 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/51/7705166.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_7705166 loop_ _publ_author_name 'He, Zhiyuan' 'Xue, Xiaolian' 'Liu, Yilan' 'Yu, Na' 'Krogman, Jeremy P.' _publ_section_title ; Aminolysis of bis[bis(trimethylsilyl)amido]-manganese, -iron, and -cobalt for the synthesis of mono- and bis-silylene complexes. ; _journal_issue 36 _journal_name_full 'Dalton transactions (Cambridge, England : 2003)' _journal_page_first 12586 _journal_page_last 12591 _journal_paper_doi 10.1039/d0dt00570c _journal_volume 49 _journal_year 2020 _chemical_formula_moiety 'C36 H50 N4' _chemical_formula_sum 'C36 H52 N4' _chemical_formula_weight 540.81 _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 mixed _atom_sites_solution_primary dual _audit_creation_date 2020-07-14 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2020-07-26 deposited with the CCDC. 2020-08-05 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 104.039(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 7.7897(4) _cell_length_b 27.7273(18) _cell_length_c 7.9686(5) _cell_measurement_reflns_used 9987 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 26.37 _cell_measurement_theta_min 2.74 _cell_volume 1669.71(17) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_reduction 'SAINT v8.37A (Bruker, 2015)' _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 150.02 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0469 _diffrn_reflns_av_unetI/netI 0.0237 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 30553 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.020 _diffrn_reflns_theta_min 2.735 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.063 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.6922 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0724 before and 0.0601 after correction. The Ratio of minimum to maximum transmission is 0.9286. The \l/2 correction factor is Not present.' _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.076 _exptl_crystal_description block _exptl_crystal_F_000 592 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.581 _refine_diff_density_min -0.604 _refine_diff_density_rms 0.046 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 187 _refine_ls_number_reflns 3278 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all 0.0647 _refine_ls_R_factor_gt 0.0508 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0625P)^2^+0.8322P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1253 _refine_ls_wR_factor_ref 0.1361 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2631 _reflns_number_total 3278 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0dt00570c2.cif _cod_data_source_block A _cod_depositor_comments 'Adding full bibliography for 7705159--7705168.cif.' _cod_database_code 7705166 _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 0.991 _shelx_estimated_absorpt_t_min 0.988 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Riding coordinates: N2(H2) 2.b Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2a), C5(H5), C6(H6), C7(H7), C8(H8) 2.c Idealised Me refined as rotating group: C12(H12a,H12b,H12c), C13(H13a,H13b,H13c), C14(H14a,H14b,H14c), C16(H16a,H16b, H16c), C17(H17a,H17b,H17c), C18(H18a,H18b,H18c) ; _shelx_res_file ; TITL mo_dincnznbr2_0m_a.res in P2(1)/n mo_dincnznbr2_0m.res created by SHELXL-2018/3 at 13:29:33 on 14-Jul-2020 REM Old TITL mo_dincnznbr2_0m in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.155, Rweak 0.006, Alpha 0.025 REM 0.535 for 86 systematic absences, Orientation as input REM Formula found by SHELXT: C18 N2 CELL 0.71073 7.7897 27.7273 7.9686 90 104.039 90 ZERR 2 0.0004 0.0018 0.0005 0 0.002 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N UNIT 72 104 8 L.S. 10 PLAN 20 SIZE 0.2 0.15 0.15 TEMP -123.13 list 4 fmap 2 53 acta REM REM REM WGHT 0.062500 0.832200 FVAR 1.24962 N1 3 0.698520 0.633945 0.372748 11.00000 0.02367 0.02636 = 0.02648 -0.00229 0.00546 -0.00168 N2 3 0.438860 0.664758 0.416073 11.00000 0.03234 0.02194 = 0.02714 -0.00209 0.00911 0.00260 AFIX 3 H2 2 0.359780 0.681148 0.339713 11.00000 -1.20000 AFIX 0 C1 1 0.561299 0.454354 0.475474 11.00000 0.02481 0.01791 = 0.02540 -0.00119 0.00757 0.00004 AFIX 43 H1 2 0.603326 0.423096 0.457249 11.00000 -1.20000 AFIX 0 C2 1 0.490637 0.483548 0.334831 11.00000 0.02707 0.02101 = 0.02090 -0.00231 0.00720 -0.00158 AFIX 43 H2A 2 0.484349 0.471911 0.221368 11.00000 -1.20000 AFIX 0 C3 1 0.428456 0.529755 0.356550 11.00000 0.01956 0.02069 = 0.02260 0.00142 0.00515 -0.00230 C4 1 0.352151 0.560086 0.201873 11.00000 0.01980 0.02189 = 0.02228 0.00013 0.00714 0.00090 C5 1 0.230469 0.539056 0.063331 11.00000 0.02594 0.02586 = 0.02475 -0.00091 0.00455 -0.00375 AFIX 43 H5 2 0.196505 0.506425 0.072116 11.00000 -1.20000 AFIX 0 C6 1 0.157958 0.564577 -0.086707 11.00000 0.02861 0.04015 = 0.02377 -0.00077 0.00011 -0.00454 AFIX 43 H6 2 0.075900 0.549474 -0.179618 11.00000 -1.20000 AFIX 0 C7 1 0.205832 0.612104 -0.100171 11.00000 0.02957 0.04006 = 0.02372 0.00870 0.00170 0.00127 AFIX 43 H7 2 0.156182 0.629879 -0.202336 11.00000 -1.20000 AFIX 0 C8 1 0.326342 0.633863 0.035420 11.00000 0.02356 0.02609 = 0.02833 0.00612 0.00799 0.00207 AFIX 43 H8 2 0.358201 0.666625 0.025515 11.00000 -1.20000 AFIX 0 C9 1 0.401635 0.608331 0.186414 11.00000 0.01793 0.02256 = 0.02193 -0.00049 0.00659 0.00117 C10 1 0.530253 0.634896 0.328611 11.00000 0.02589 0.01690 = 0.02143 0.00235 0.00735 -0.00107 C11 1 0.818788 0.605979 0.294080 11.00000 0.01984 0.02776 = 0.03153 -0.00215 0.00498 0.00039 C12 1 0.958356 0.642168 0.270143 11.00000 0.03363 0.04111 = 0.08288 -0.01382 0.02953 -0.00932 AFIX 137 H12A 2 0.903355 0.666315 0.183998 11.00000 -1.50000 H12B 2 1.051757 0.625269 0.230472 11.00000 -1.50000 H12C 2 1.009643 0.658173 0.380578 11.00000 -1.50000 AFIX 0 C13 1 0.905886 0.568181 0.427205 11.00000 0.04048 0.05277 = 0.04780 0.00859 0.00289 0.01716 AFIX 137 H13A 2 0.960308 0.584125 0.536977 11.00000 -1.50000 H13B 2 0.996993 0.550938 0.385091 11.00000 -1.50000 H13C 2 0.816219 0.545236 0.444928 11.00000 -1.50000 AFIX 0 C14 1 0.744993 0.581284 0.120789 11.00000 0.02771 0.04528 = 0.03786 -0.00947 0.01320 0.00380 AFIX 137 H14A 2 0.664703 0.555284 0.135544 11.00000 -1.50000 H14B 2 0.842595 0.567821 0.077885 11.00000 -1.50000 H14C 2 0.680210 0.604864 0.037465 11.00000 -1.50000 AFIX 0 C15 1 0.516223 0.697479 0.560384 11.00000 0.04942 0.02199 = 0.03321 -0.00888 0.01928 -0.00899 C16 1 0.624878 0.669009 0.713954 11.00000 0.05769 0.04793 = 0.02906 -0.00996 0.00786 -0.00777 AFIX 137 H16A 2 0.549632 0.644639 0.749420 11.00000 -1.50000 H16B 2 0.670882 0.691033 0.810589 11.00000 -1.50000 H16C 2 0.723810 0.653096 0.680353 11.00000 -1.50000 AFIX 0 C17 1 0.628055 0.736550 0.503286 11.00000 0.07495 0.03408 = 0.06281 -0.01316 0.03742 -0.02310 AFIX 137 H17A 2 0.728774 0.721596 0.469775 11.00000 -1.50000 H17B 2 0.671498 0.759031 0.599075 11.00000 -1.50000 H17C 2 0.555665 0.754096 0.404362 11.00000 -1.50000 AFIX 0 C18 1 0.357795 0.720737 0.611614 11.00000 0.07022 0.03020 = 0.05274 -0.00989 0.03457 0.00000 AFIX 137 H18A 2 0.287527 0.738944 0.513276 11.00000 -1.50000 H18B 2 0.400369 0.742601 0.709501 11.00000 -1.50000 H18C 2 0.284208 0.695537 0.644816 11.00000 -1.50000 AFIX 0 HKLF 4 REM mo_dincnznbr2_0m_a.res in P2(1)/n REM wR2 = 0.1361, GooF = S = 1.044, Restrained GooF = 1.044 for all data REM R1 = 0.0508 for 2631 Fo > 4sig(Fo) and 0.0647 for all 3278 data REM 187 parameters refined using 0 restraints END WGHT 0.0623 0.8363 REM Highest difference peak 0.581, deepest hole -0.604, 1-sigma level 0.046 Q1 1 0.3135 0.6592 0.3849 11.00000 0.05 0.58 Q2 1 0.4064 0.5812 0.1880 11.00000 0.05 0.18 Q3 1 0.3938 0.5405 0.2937 11.00000 0.05 0.16 Q4 1 0.4588 0.6197 0.2514 11.00000 0.05 0.15 Q5 1 0.5035 0.5173 0.3484 11.00000 0.05 0.15 Q6 1 0.4481 0.5414 0.4337 11.00000 0.05 0.14 Q7 1 0.8855 0.6220 0.2784 11.00000 0.05 0.14 Q8 1 1.0783 0.6202 0.2739 11.00000 0.05 0.13 Q9 1 0.6837 0.7362 0.3876 11.00000 0.05 0.12 Q10 1 0.9508 0.6801 0.3084 11.00000 0.05 0.12 Q11 1 0.7019 0.6793 0.3550 11.00000 0.05 0.12 Q12 1 0.7808 0.6794 0.0223 11.00000 0.05 0.12 Q13 1 0.2544 0.6412 0.4803 11.00000 0.05 0.12 Q14 1 0.6684 0.4171 0.4954 11.00000 0.05 0.11 Q15 1 1.0298 0.6462 0.4950 11.00000 0.05 0.11 Q16 1 0.5768 0.7450 0.3922 11.00000 0.05 0.11 Q17 1 0.8783 0.6661 0.1422 11.00000 0.05 0.11 Q18 1 0.9945 0.5424 0.3495 11.00000 0.05 0.11 Q19 1 0.5245 0.3992 0.4253 11.00000 0.05 0.11 Q20 1 0.4097 0.5049 0.3526 11.00000 0.05 0.11 ; _shelx_res_checksum 88781 _olex2_submission_special_instructions 'No special instructions were received' 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 N1 N 0.69852(17) 0.63395(5) 0.37275(16) 0.0256(3) Uani 1 1 d . . . . . N2 N 0.43886(18) 0.66476(5) 0.41607(17) 0.0268(3) Uani 1 1 d . . . . . H2 H 0.359780 0.681148 0.339713 0.032 Uiso 1 1 d R . . . . C1 C 0.56130(19) 0.45435(5) 0.47547(18) 0.0225(3) Uani 1 1 d . . . . . H1 H 0.603326 0.423096 0.457249 0.027 Uiso 1 1 calc R . . . . C2 C 0.4906(2) 0.48355(5) 0.33483(19) 0.0228(3) Uani 1 1 d . . . . . H2A H 0.484349 0.471911 0.221368 0.027 Uiso 1 1 calc R . . . . C3 C 0.42846(19) 0.52975(5) 0.35655(18) 0.0209(3) Uani 1 1 d . . . . . C4 C 0.35215(19) 0.56009(5) 0.20187(18) 0.0210(3) Uani 1 1 d . . . . . C5 C 0.2305(2) 0.53906(6) 0.06333(19) 0.0258(3) Uani 1 1 d . . . . . H5 H 0.196505 0.506425 0.072116 0.031 Uiso 1 1 calc R . . . . C6 C 0.1580(2) 0.56458(6) -0.0867(2) 0.0319(4) Uani 1 1 d . . . . . H6 H 0.075900 0.549474 -0.179618 0.038 Uiso 1 1 calc R . . . . C7 C 0.2058(2) 0.61210(6) -0.1002(2) 0.0319(4) Uani 1 1 d . . . . . H7 H 0.156182 0.629879 -0.202336 0.038 Uiso 1 1 calc R . . . . C8 C 0.3263(2) 0.63386(6) 0.0354(2) 0.0257(3) Uani 1 1 d . . . . . H8 H 0.358201 0.666625 0.025515 0.031 Uiso 1 1 calc R . . . . C9 C 0.40163(18) 0.60833(5) 0.18641(18) 0.0205(3) Uani 1 1 d . . . . . C10 C 0.5303(2) 0.63490(5) 0.32861(19) 0.0211(3) Uani 1 1 d . . . . . C11 C 0.8188(2) 0.60598(6) 0.2941(2) 0.0266(4) Uani 1 1 d . . . . . C12 C 0.9584(3) 0.64217(7) 0.2701(3) 0.0499(5) Uani 1 1 d . . . . . H12A H 0.903355 0.666315 0.183998 0.075 Uiso 1 1 calc GR . . . . H12B H 1.051757 0.625269 0.230472 0.075 Uiso 1 1 calc GR . . . . H12C H 1.009643 0.658173 0.380578 0.075 Uiso 1 1 calc GR . . . . C13 C 0.9059(3) 0.56818(8) 0.4272(3) 0.0484(5) Uani 1 1 d . . . . . H13A H 0.960308 0.584125 0.536977 0.073 Uiso 1 1 calc GR . . . . H13B H 0.996993 0.550938 0.385091 0.073 Uiso 1 1 calc GR . . . . H13C H 0.816219 0.545236 0.444928 0.073 Uiso 1 1 calc GR . . . . C14 C 0.7450(2) 0.58128(7) 0.1208(2) 0.0360(4) Uani 1 1 d . . . . . H14A H 0.664703 0.555284 0.135544 0.054 Uiso 1 1 calc GR . . . . H14B H 0.842595 0.567821 0.077885 0.054 Uiso 1 1 calc GR . . . . H14C H 0.680210 0.604864 0.037465 0.054 Uiso 1 1 calc GR . . . . C15 C 0.5162(3) 0.69748(6) 0.5604(2) 0.0333(4) Uani 1 1 d . . . . . C16 C 0.6249(3) 0.66901(7) 0.7140(2) 0.0454(5) Uani 1 1 d . . . . . H16A H 0.549632 0.644639 0.749420 0.068 Uiso 1 1 calc GR . . . . H16B H 0.670882 0.691033 0.810589 0.068 Uiso 1 1 calc GR . . . . H16C H 0.723810 0.653096 0.680353 0.068 Uiso 1 1 calc GR . . . . C17 C 0.6281(3) 0.73655(7) 0.5033(3) 0.0537(6) Uani 1 1 d . . . . . H17A H 0.728774 0.721596 0.469775 0.081 Uiso 1 1 calc GR . . . . H17B H 0.671498 0.759031 0.599075 0.081 Uiso 1 1 calc GR . . . . H17C H 0.555665 0.754096 0.404362 0.081 Uiso 1 1 calc GR . . . . C18 C 0.3578(3) 0.72074(7) 0.6116(3) 0.0477(5) Uani 1 1 d . . . . . H18A H 0.287527 0.738944 0.513276 0.072 Uiso 1 1 calc GR . . . . H18B H 0.400369 0.742601 0.709501 0.072 Uiso 1 1 calc GR . . . . H18C H 0.284208 0.695537 0.644816 0.072 Uiso 1 1 calc GR . . . . 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 N1 0.0237(7) 0.0264(7) 0.0265(7) -0.0023(5) 0.0055(5) -0.0017(5) N2 0.0323(7) 0.0219(6) 0.0271(7) -0.0021(5) 0.0091(6) 0.0026(5) C1 0.0248(8) 0.0179(7) 0.0254(8) -0.0012(6) 0.0076(6) 0.0000(6) C2 0.0271(8) 0.0210(7) 0.0209(7) -0.0023(6) 0.0072(6) -0.0016(6) C3 0.0196(7) 0.0207(7) 0.0226(7) 0.0014(6) 0.0052(6) -0.0023(6) C4 0.0198(7) 0.0219(7) 0.0223(7) 0.0001(6) 0.0071(6) 0.0009(6) C5 0.0259(8) 0.0259(8) 0.0248(8) -0.0009(6) 0.0045(6) -0.0038(6) C6 0.0286(9) 0.0402(9) 0.0238(8) -0.0008(7) 0.0001(6) -0.0045(7) C7 0.0296(9) 0.0401(9) 0.0237(8) 0.0087(7) 0.0017(7) 0.0013(7) C8 0.0236(8) 0.0261(8) 0.0283(8) 0.0061(6) 0.0080(6) 0.0021(6) C9 0.0179(7) 0.0226(7) 0.0219(7) -0.0005(6) 0.0066(6) 0.0012(5) C10 0.0259(8) 0.0169(7) 0.0214(7) 0.0024(6) 0.0074(6) -0.0011(6) C11 0.0198(8) 0.0278(8) 0.0315(8) -0.0022(6) 0.0050(6) 0.0004(6) C12 0.0336(10) 0.0411(11) 0.0829(16) -0.0138(10) 0.0295(10) -0.0093(8) C13 0.0405(11) 0.0528(12) 0.0478(12) 0.0086(9) 0.0029(9) 0.0172(9) C14 0.0277(9) 0.0453(10) 0.0379(10) -0.0095(8) 0.0132(7) 0.0038(7) C15 0.0494(11) 0.0220(8) 0.0332(9) -0.0089(7) 0.0193(8) -0.0090(7) C16 0.0577(13) 0.0479(11) 0.0291(9) -0.0100(8) 0.0079(8) -0.0078(9) C17 0.0750(15) 0.0341(10) 0.0628(13) -0.0132(9) 0.0374(12) -0.0231(10) C18 0.0702(14) 0.0302(9) 0.0527(12) -0.0099(9) 0.0346(11) 0.0000(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' 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 N1 C11 127.88(13) . . ? C10 N2 C15 126.71(14) . . ? C2 C1 C3 120.79(14) . 3_666 ? C1 C2 C3 121.23(13) . . ? C1 C3 C2 117.96(13) 3_666 . ? C1 C3 C4 122.29(13) 3_666 . ? C2 C3 C4 119.74(13) . . ? C5 C4 C3 118.42(13) . . ? C5 C4 C9 118.43(13) . . ? C9 C4 C3 123.11(13) . . ? C6 C5 C4 121.68(14) . . ? C7 C6 C5 119.54(15) . . ? C6 C7 C8 119.97(15) . . ? C7 C8 C9 120.96(14) . . ? C4 C9 C10 123.00(13) . . ? C8 C9 C4 119.41(13) . . ? C8 C9 C10 117.57(13) . . ? N1 C10 N2 119.61(14) . . ? N1 C10 C9 130.46(13) . . ? N2 C10 C9 109.92(13) . . ? N1 C11 C12 104.71(13) . . ? N1 C11 C13 106.71(13) . . ? N1 C11 C14 118.99(13) . . ? C12 C11 C13 109.16(15) . . ? C14 C11 C12 107.82(15) . . ? C14 C11 C13 109.11(15) . . ? N2 C15 C16 110.43(13) . . ? N2 C15 C17 111.04(14) . . ? N2 C15 C18 105.28(15) . . ? C16 C15 C18 109.23(15) . . ? C17 C15 C16 111.10(17) . . ? C17 C15 C18 109.58(15) . . ? 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 N1 C10 1.272(2) . ? N1 C11 1.469(2) . ? N2 C10 1.3852(19) . ? N2 C15 1.474(2) . ? C1 C2 1.384(2) . ? C1 C3 1.393(2) 3_666 ? C2 C3 1.395(2) . ? C3 C4 1.491(2) . ? C4 C5 1.396(2) . ? C4 C9 1.406(2) . ? C5 C6 1.386(2) . ? C6 C7 1.381(2) . ? C7 C8 1.386(2) . ? C8 C9 1.397(2) . ? C9 C10 1.510(2) . ? C11 C12 1.525(2) . ? C11 C13 1.528(2) . ? C11 C14 1.523(2) . ? C15 C16 1.528(3) . ? C15 C17 1.527(2) . ? C15 C18 1.533(3) . ?