#------------------------------------------------------------------------------ #$Date: 2020-10-06 14:10:40 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257958 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240441.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_7240441 loop_ _publ_author_name 'Zhang, Hua' 'Zhan, Xiao-Yu' 'Dong, Yu' 'Yang, Jian' 'He, Shuai' 'Shi, Zhi-Chuan' 'Zhang, Xiao-Mei' 'Wang, Ji-Yu' _publ_section_title ; Dehydration in water: frustrated Lewis pairs directly catalyzed allylization of electron-rich arenes and allyl alcohols ; _journal_issue 29 _journal_name_full 'RSC Advances' _journal_page_first 16942 _journal_page_last 16948 _journal_paper_doi 10.1039/D0RA02912B _journal_volume 10 _journal_year 2020 _chemical_formula_moiety 'C36 H30 N2' _chemical_formula_sum 'C36 H30 N2' _chemical_formula_weight 490.62 _space_group_crystal_system tetragonal _space_group_IT_number 88 _space_group_name_Hall '-I 4ad' _space_group_name_H-M_alt 'I 41/a :2' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _audit_block_doi 10.5517/ccdc.csd.cc244tfk _audit_creation_date 2019-10-24 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-12-09 deposited with the CCDC. 2020-04-23 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 20.2031(8) _cell_length_b 20.2031(8) _cell_length_c 13.2367(7) _cell_measurement_reflns_used 1428 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25.4050 _cell_measurement_theta_min 3.3680 _cell_volume 5402.8(4) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) ; _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 'olex2.solve (Bourhis et al., 2015)' _diffrn_ambient_temperature 293.15 _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.0874 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -17.00 24.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -14.8106 -99.0000 -90.0000 41 #__ type_ start__ end____ width___ exp.time_ 2 omega -62.00 -36.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -14.8106 -178.0000 -150.0000 26 #__ type_ start__ end____ width___ exp.time_ 3 omega 1.00 77.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 16.8419 77.0000 30.0000 76 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0260552000 _diffrn_orient_matrix_UB_12 0.0216052000 _diffrn_orient_matrix_UB_13 -0.0142523000 _diffrn_orient_matrix_UB_21 -0.0225544000 _diffrn_orient_matrix_UB_22 0.0268897000 _diffrn_orient_matrix_UB_23 -0.0009795000 _diffrn_orient_matrix_UB_31 0.0067630000 _diffrn_orient_matrix_UB_32 0.0064822000 _diffrn_orient_matrix_UB_33 0.0516479000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_unetI/netI 0.0546 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 7894 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.371 _diffrn_reflns_theta_min 3.393 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.92375 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.206 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2080 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.25 _refine_diff_density_max 0.527 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.039 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 173 _refine_ls_number_reflns 2769 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.069 _refine_ls_R_factor_all 0.1507 _refine_ls_R_factor_gt 0.0756 _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^)+(0.1088P)^2^+0.2582P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2006 _refine_ls_wR_factor_ref 0.2523 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1284 _reflns_number_total 2769 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra02912b2.cif _cod_data_source_block 191024_s4_zh _cod_depositor_comments 'Adding full bibliography for 7240441--7240442.cif.' _cod_original_cell_volume 5402.8(5) _cod_original_sg_symbol_H-M 'I 41/a' _cod_database_code 7240441 _shelx_shelxl_version_number 2014/7 _chemical_oxdiff_formula c12h12n2o2 _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 0.983 _shelx_estimated_absorpt_t_min 0.976 _reflns_odcompleteness_completeness 99.76 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _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 2.a Ternary CH refined with riding coordinates: C10(H10) 2.b Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18) 2.c Idealised Me refined as rotating group: C9(H9A,H9B,H9C) ; _shelx_res_file ; 191024_s4_zh.res created by SHELXL-2014/7 TITL CELL 0.71073 20.20314 20.20314 13.23669 90 90 90 ZERR 8 0.00079 0.00079 0.00072 0 0 0 LATT 2 SYMM 0.75-Y,0.25+X,0.25+Z SYMM -X,0.5-Y,+Z SYMM 0.25+Y,0.25-X,0.25+Z SFAC C H N UNIT 288 240 16 L.S. 4 PLAN 20 SIZE 0.25 0.3 0.35 TEMP 20 fmap 2 htab conf bond $h acta SHEL 999 0.8 REM REM REM WGHT 0.108800 0.258200 FVAR 1.46465 N1 3 0.020779 0.115313 0.749269 11.00000 0.09461 0.05225 = 0.05133 0.00110 0.00291 -0.01186 C1 1 0.088355 0.109046 0.745467 11.00000 0.08568 0.07665 = 0.04672 0.00203 0.00737 0.00890 C2 1 0.128474 0.053364 0.732594 11.00000 0.13658 0.08064 = 0.06308 0.00441 0.01629 0.02440 AFIX 43 H2 2 0.110524 0.011240 0.725364 11.00000 -1.20000 AFIX 0 C3 1 0.195461 0.063686 0.731116 11.00000 0.13165 0.13979 = 0.08724 0.01653 0.03493 0.05994 AFIX 43 H3 2 0.223346 0.027554 0.721964 11.00000 -1.20000 AFIX 0 C4 1 0.222842 0.124947 0.742555 11.00000 0.09013 0.14884 = 0.08494 0.02082 0.01537 0.02887 AFIX 43 H4 2 0.268650 0.129478 0.742161 11.00000 -1.20000 AFIX 0 C5 1 0.183657 0.180256 0.754693 11.00000 0.07024 0.11799 = 0.07100 0.00356 0.01476 0.00842 AFIX 43 H5 2 0.202713 0.221815 0.762874 11.00000 -1.20000 AFIX 0 C6 1 0.115552 0.172995 0.754519 11.00000 0.06723 0.07894 = 0.04005 0.00086 0.00716 -0.00161 C7 1 0.061414 0.218394 0.763067 11.00000 0.05439 0.06961 = 0.04101 -0.00530 0.00142 -0.00454 C8 1 0.004716 0.181641 0.760638 11.00000 0.06580 0.05617 = 0.03813 0.00073 -0.00103 -0.00438 C9 1 -0.025728 0.060079 0.746192 11.00000 0.12648 0.06287 = 0.07551 -0.00658 0.00188 -0.03056 AFIX 137 H9A 2 -0.008863 0.026213 0.702311 11.00000 -1.50000 H9B 2 -0.067678 0.075283 0.721254 11.00000 -1.50000 H9C 2 -0.031238 0.042407 0.812988 11.00000 -1.50000 AFIX 0 C10 1 0.064182 0.292173 0.770929 11.00000 0.06431 0.06146 = 0.04766 -0.00530 0.00373 -0.01878 AFIX 13 H10 2 0.090188 0.308781 0.713803 11.00000 -1.20000 AFIX 0 C11 1 0.096182 0.316888 0.867202 11.00000 0.07943 0.07785 = 0.07135 -0.00622 -0.00602 -0.00530 AFIX 43 H11 2 0.109085 0.361075 0.867144 11.00000 -1.20000 AFIX 0 C12 1 0.107400 0.285816 0.946094 11.00000 0.09225 0.07577 = 0.06688 -0.00465 0.00874 -0.00167 AFIX 43 H12 2 0.095034 0.241476 0.945972 11.00000 -1.20000 AFIX 0 C13 1 0.138523 0.310840 1.042059 11.00000 0.07395 0.07303 = 0.06124 -0.00847 -0.00968 0.01529 C14 1 0.168659 0.371063 1.049563 11.00000 0.11444 0.08254 = 0.05771 0.00638 -0.00456 0.01349 AFIX 43 H14 2 0.172220 0.397643 0.992459 11.00000 -1.20000 AFIX 0 C15 1 0.194028 0.393361 1.140487 11.00000 0.12409 0.08020 = 0.09304 -0.01125 -0.00835 -0.01203 AFIX 43 H15 2 0.214699 0.434442 1.143558 11.00000 -1.20000 AFIX 0 C16 1 0.189041 0.355813 1.225411 11.00000 0.12138 0.12225 = 0.06385 -0.01144 -0.01944 -0.01883 AFIX 43 H16 2 0.204860 0.370917 1.287233 11.00000 -1.20000 AFIX 0 C17 1 0.160079 0.295409 1.216535 11.00000 0.13886 0.13724 = 0.06483 0.02992 -0.02729 -0.03658 AFIX 43 H17 2 0.156557 0.268467 1.273249 11.00000 -1.20000 AFIX 0 C18 1 0.135840 0.273203 1.125490 11.00000 0.10536 0.10087 = 0.07045 0.01289 -0.02479 -0.02340 AFIX 43 H18 2 0.117190 0.231192 1.121695 11.00000 -1.20000 AFIX 0 HKLF 4 REM REM R1 = 0.0756 for 1284 Fo > 4sig(Fo) and 0.1507 for all 2769 data REM 173 parameters refined using 0 restraints END WGHT 0.1080 0.3272 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.527, deepest hole -0.206, 1-sigma level 0.039 Q1 1 0.1403 0.3310 0.9318 11.00000 0.05 0.53 Q2 1 0.0373 0.2579 0.9576 11.00000 0.05 0.13 Q3 1 0.0598 0.2911 0.9023 11.00000 0.05 0.12 Q4 1 0.0756 0.2268 1.1265 11.00000 0.05 0.12 Q5 1 0.0767 0.0291 0.7189 11.00000 0.05 0.12 Q6 1 0.2372 0.4129 1.1575 11.00000 0.05 0.12 Q7 1 0.2098 0.4045 1.0485 11.00000 0.05 0.12 Q8 1 -0.0131 0.1911 0.7619 11.00000 0.05 0.11 Q9 1 0.1909 0.2472 1.2332 11.00000 0.05 0.11 Q10 1 0.1504 0.1728 1.1388 11.00000 0.05 0.10 Q11 1 0.1428 0.3820 1.0633 11.00000 0.05 0.10 Q12 1 0.1125 0.3924 1.2149 11.00000 0.05 0.09 Q13 1 -0.0695 0.0736 0.7674 11.00000 0.05 0.09 Q14 1 0.1674 0.3098 0.7452 11.00000 0.05 0.09 Q15 1 0.1230 0.1773 1.0899 11.00000 0.05 0.09 Q16 1 0.0000 0.2500 1.1250 10.25000 0.05 0.09 Q17 1 0.0601 0.1720 0.9395 11.00000 0.05 0.09 Q18 1 0.0711 -0.0512 0.7110 11.00000 0.05 0.08 Q19 1 0.1385 0.2141 0.9431 11.00000 0.05 0.08 Q20 1 0.1048 0.4065 1.2263 11.00000 0.05 0.08 ; _shelx_res_checksum 97012 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-y+3/4, x+1/4, z+1/4' '-x, -y+1/2, z' 'y+1/4, -x+1/4, z+1/4' 'x+1/2, y+1/2, z+1/2' '-y+5/4, x+3/4, z+3/4' '-x+1/2, -y+1, z+1/2' 'y+3/4, -x+3/4, z+3/4' '-x, -y, -z' 'y-3/4, -x-1/4, -z-1/4' 'x, y-1/2, -z' '-y-1/4, x-1/4, -z-1/4' '-x+1/2, -y+1/2, -z+1/2' 'y-1/4, -x+1/4, -z+1/4' 'x+1/2, y, -z+1/2' '-y+1/4, x+1/4, -z+1/4' 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 0.02078(15) 0.11531(12) 0.74927(17) 0.0661(8) Uani 1 1 d . . . . . C1 C 0.08836(19) 0.10905(18) 0.7455(2) 0.0697(9) Uani 1 1 d . . . . . C2 C 0.1285(3) 0.0534(2) 0.7326(3) 0.0934(13) Uani 1 1 d . . . . . H2 H 0.1105 0.0112 0.7254 0.112 Uiso 1 1 calc R . . . . C3 C 0.1955(3) 0.0637(3) 0.7311(3) 0.1196(19) Uani 1 1 d . . . . . H3 H 0.2233 0.0276 0.7220 0.143 Uiso 1 1 calc R . . . . C4 C 0.2228(2) 0.1249(3) 0.7426(3) 0.1080(15) Uani 1 1 d . . . . . H4 H 0.2687 0.1295 0.7422 0.130 Uiso 1 1 calc R . . . . C5 C 0.18366(19) 0.1803(2) 0.7547(3) 0.0864(11) Uani 1 1 d . . . . . H5 H 0.2027 0.2218 0.7629 0.104 Uiso 1 1 calc R . . . . C6 C 0.11555(17) 0.17299(17) 0.7545(2) 0.0621(9) Uani 1 1 d . . . . . C7 C 0.06141(15) 0.21839(15) 0.76307(19) 0.0550(8) Uani 1 1 d . . . . . C8 C 0.00472(15) 0.18164(14) 0.76064(19) 0.0534(8) Uani 1 1 d . . . . . C9 C -0.0257(2) 0.06008(17) 0.7462(3) 0.0883(12) Uani 1 1 d . . . . . H9A H -0.0089 0.0262 0.7023 0.132 Uiso 1 1 calc GR . . . . H9B H -0.0677 0.0753 0.7213 0.132 Uiso 1 1 calc GR . . . . H9C H -0.0312 0.0424 0.8130 0.132 Uiso 1 1 calc GR . . . . C10 C 0.06418(15) 0.29217(15) 0.7709(2) 0.0578(8) Uani 1 1 d . . . . . H10 H 0.0902 0.3088 0.7138 0.069 Uiso 1 1 calc R . . . . C11 C 0.09618(17) 0.31689(19) 0.8672(2) 0.0762(10) Uani 1 1 d . . . . . H11 H 0.1091 0.3611 0.8671 0.091 Uiso 1 1 calc R . . . . C12 C 0.10740(17) 0.28582(18) 0.9461(3) 0.0783(10) Uani 1 1 d . . . . . H12 H 0.0950 0.2415 0.9460 0.094 Uiso 1 1 calc R . . . . C13 C 0.13852(16) 0.31084(18) 1.0421(2) 0.0694(9) Uani 1 1 d . . . . . C14 C 0.16866(19) 0.37106(19) 1.0496(3) 0.0849(11) Uani 1 1 d . . . . . H14 H 0.1722 0.3976 0.9925 0.102 Uiso 1 1 calc R . . . . C15 C 0.1940(2) 0.3934(2) 1.1405(3) 0.0991(13) Uani 1 1 d . . . . . H15 H 0.2147 0.4344 1.1436 0.119 Uiso 1 1 calc R . . . . C16 C 0.1890(2) 0.3558(3) 1.2254(3) 0.1025(14) Uani 1 1 d . . . . . H16 H 0.2049 0.3709 1.2872 0.123 Uiso 1 1 calc R . . . . C17 C 0.1601(2) 0.2954(3) 1.2165(3) 0.1136(15) Uani 1 1 d . . . . . H17 H 0.1566 0.2685 1.2732 0.136 Uiso 1 1 calc R . . . . C18 C 0.1358(2) 0.2732(2) 1.1255(3) 0.0922(13) Uani 1 1 d . . . . . H18 H 0.1172 0.2312 1.1217 0.111 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 N1 0.095(2) 0.0522(16) 0.0513(14) 0.0011(12) 0.0029(14) -0.0119(15) C1 0.086(3) 0.077(2) 0.0467(17) 0.0020(16) 0.0074(16) 0.009(2) C2 0.137(4) 0.081(3) 0.063(2) 0.0044(18) 0.016(2) 0.024(3) C3 0.132(5) 0.140(5) 0.087(3) 0.017(3) 0.035(3) 0.060(4) C4 0.090(3) 0.149(5) 0.085(3) 0.021(3) 0.015(2) 0.029(3) C5 0.070(2) 0.118(3) 0.071(2) 0.004(2) 0.0148(18) 0.008(2) C6 0.067(2) 0.079(2) 0.0401(15) 0.0009(14) 0.0072(14) -0.0016(18) C7 0.0544(18) 0.070(2) 0.0410(15) -0.0053(13) 0.0014(13) -0.0045(16) C8 0.066(2) 0.0562(19) 0.0381(14) 0.0007(13) -0.0010(13) -0.0044(15) C9 0.126(3) 0.063(2) 0.076(2) -0.0066(17) 0.002(2) -0.031(2) C10 0.0643(19) 0.0615(19) 0.0477(16) -0.0053(13) 0.0037(14) -0.0188(15) C11 0.079(2) 0.078(2) 0.071(2) -0.0062(19) -0.0060(18) -0.0053(18) C12 0.092(3) 0.076(2) 0.067(2) -0.005(2) 0.0087(19) -0.0017(18) C13 0.074(2) 0.073(2) 0.061(2) -0.0085(18) -0.0097(17) 0.0153(17) C14 0.114(3) 0.083(3) 0.058(2) 0.0064(19) -0.005(2) 0.013(2) C15 0.124(4) 0.080(3) 0.093(3) -0.011(2) -0.008(3) -0.012(2) C16 0.121(4) 0.122(4) 0.064(2) -0.011(2) -0.019(2) -0.019(3) C17 0.139(4) 0.137(4) 0.065(2) 0.030(2) -0.027(2) -0.037(3) C18 0.105(3) 0.101(3) 0.070(2) 0.013(2) -0.025(2) -0.023(2) 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 C1 N1 C8 109.0(3) . . ? C1 N1 C9 124.7(3) . . ? C8 N1 C9 126.2(3) . . ? N1 C1 C2 131.0(4) . . ? N1 C1 C6 107.5(3) . . ? C2 C1 C6 121.5(4) . . ? C1 C2 H2 121.5 . . ? C3 C2 C1 116.9(4) . . ? C3 C2 H2 121.5 . . ? C2 C3 H3 118.7 . . ? C4 C3 C2 122.5(5) . . ? C4 C3 H3 118.7 . . ? C3 C4 H4 119.5 . . ? C3 C4 C5 121.0(5) . . ? C5 C4 H4 119.5 . . ? C4 C5 H5 120.5 . . ? C4 C5 C6 119.0(4) . . ? C6 C5 H5 120.5 . . ? C1 C6 C7 107.2(3) . . ? C5 C6 C1 119.0(3) . . ? C5 C6 C7 133.7(3) . . ? C6 C7 C10 128.0(3) . . ? C8 C7 C6 106.9(3) . . ? C8 C7 C10 125.1(3) . . ? N1 C8 C10 124.7(3) . 3 ? C7 C8 N1 109.4(3) . . ? C7 C8 C10 125.9(3) . 3 ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 C8 108.2(2) . 3 ? C7 C10 H10 107.9 . . ? C7 C10 C11 113.8(2) . . ? C8 C10 H10 107.9 3 . ? C8 C10 C11 110.9(2) 3 . ? C11 C10 H10 107.9 . . ? C10 C11 H11 115.8 . . ? C12 C11 C10 128.3(3) . . ? C12 C11 H11 115.8 . . ? C11 C12 H12 115.9 . . ? C11 C12 C13 128.1(4) . . ? C13 C12 H12 115.9 . . ? C14 C13 C12 123.2(3) . . ? C18 C13 C12 119.2(4) . . ? C18 C13 C14 117.6(3) . . ? C13 C14 H14 119.4 . . ? C13 C14 C15 121.3(4) . . ? C15 C14 H14 119.4 . . ? C14 C15 H15 119.7 . . ? C16 C15 C14 120.7(4) . . ? C16 C15 H15 119.7 . . ? C15 C16 H16 121.3 . . ? C17 C16 C15 117.5(4) . . ? C17 C16 H16 121.3 . . ? C16 C17 H17 119.3 . . ? C16 C17 C18 121.5(4) . . ? C18 C17 H17 119.3 . . ? C13 C18 C17 121.4(4) . . ? C13 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? 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 C1 1.372(4) . ? N1 C8 1.387(4) . ? N1 C9 1.459(4) . ? C1 C2 1.397(5) . ? C1 C6 1.409(4) . ? C2 H2 0.9300 . ? C2 C3 1.369(6) . ? C3 H3 0.9300 . ? C3 C4 1.364(7) . ? C4 H4 0.9300 . ? C4 C5 1.379(6) . ? C5 H5 0.9300 . ? C5 C6 1.384(5) . ? C6 C7 1.432(4) . ? C7 C8 1.365(4) . ? C7 C10 1.495(4) . ? C8 C10 1.495(4) 3 ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C8 1.495(4) 3 ? C10 H10 0.9800 . ? C10 C11 1.514(4) . ? C11 H11 0.9300 . ? C11 C12 1.239(4) . ? C12 H12 0.9300 . ? C12 C13 1.505(5) . ? C13 C14 1.364(5) . ? C13 C18 1.342(4) . ? C14 H14 0.9300 . ? C14 C15 1.384(5) . ? C15 H15 0.9300 . ? C15 C16 1.360(5) . ? C16 H16 0.9300 . ? C16 C17 1.358(6) . ? C17 H17 0.9300 . ? C17 C18 1.376(5) . ? C18 H18 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 C1 C2 C3 179.3(3) . . . . ? N1 C1 C6 C5 178.9(2) . . . . ? N1 C1 C6 C7 -0.5(3) . . . . ? C1 N1 C8 C7 0.7(3) . . . . ? C1 N1 C8 C10 -178.0(2) . . . 3 ? C1 C2 C3 C4 0.6(6) . . . . ? C1 C6 C7 C8 0.9(3) . . . . ? C1 C6 C7 C10 -177.8(2) . . . . ? C2 C1 C6 C5 -2.6(4) . . . . ? C2 C1 C6 C7 178.0(3) . . . . ? C2 C3 C4 C5 -1.1(7) . . . . ? C3 C4 C5 C6 -0.4(6) . . . . ? C4 C5 C6 C1 2.2(4) . . . . ? C4 C5 C6 C7 -178.7(3) . . . . ? C5 C6 C7 C8 -178.3(3) . . . . ? C5 C6 C7 C10 3.0(5) . . . . ? C6 C1 C2 C3 1.2(5) . . . . ? C6 C7 C8 N1 -1.0(3) . . . . ? C6 C7 C8 C10 177.7(2) . . . 3 ? C6 C7 C10 C8 170.5(2) . . . 3 ? C6 C7 C10 C11 -65.7(4) . . . . ? C7 C10 C11 C12 -16.0(5) . . . . ? C8 N1 C1 C2 -178.4(3) . . . . ? C8 N1 C1 C6 -0.1(3) . . . . ? C8 C7 C10 C8 -8.0(3) . . . 3 ? C8 C7 C10 C11 115.8(3) . . . . ? C8 C10 C11 C12 106.2(4) 3 . . . ? C9 N1 C1 C2 4.1(5) . . . . ? C9 N1 C1 C6 -177.6(3) . . . . ? C9 N1 C8 C7 178.2(3) . . . . ? C9 N1 C8 C10 -0.5(4) . . . 3 ? C10 C7 C8 N1 177.8(2) . . . . ? C10 C7 C8 C10 -3.5(4) . . . 3 ? C10 C11 C12 C13 -179.2(3) . . . . ? C11 C12 C13 C14 -10.6(6) . . . . ? C11 C12 C13 C18 168.1(4) . . . . ? C12 C13 C14 C15 177.1(3) . . . . ? C12 C13 C18 C17 -176.1(4) . . . . ? C13 C14 C15 C16 -0.6(6) . . . . ? C14 C13 C18 C17 2.6(6) . . . . ? C14 C15 C16 C17 1.8(7) . . . . ? C15 C16 C17 C18 -0.8(7) . . . . ? C16 C17 C18 C13 -1.4(7) . . . . ? C18 C13 C14 C15 -1.7(6) . . . . ?