#------------------------------------------------------------------------------ #$Date: 2021-11-06 22:40:57 +0200 (Sat, 06 Nov 2021) $ #$Revision: 270497 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158328.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_7158328 loop_ _publ_author_name 'Marras, Valentina' 'Caboni, Pierluigi' 'Secci, Francesco' 'Guillot, R\'egis' 'Aitken, David J.' 'Frongia, Angelo' _publ_section_title ; A Br\/onsted acid catalyzed tandem reaction for the diastereoselective synthesis of cyclobuta-fused tetrahydroquinoline carboxylic esters. ; _journal_issue 41 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 8912 _journal_page_last 8916 _journal_paper_doi 10.1039/d1ob01518d _journal_volume 19 _journal_year 2021 _chemical_formula_moiety 'C18 H18 N2 O2' _chemical_formula_sum 'C18 H18 N2 O2' _chemical_formula_weight 294.34 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2021-05-31 deposited with the CCDC. 2021-09-30 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 95.4260(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.56070(10) _cell_length_b 7.5167(2) _cell_length_c 28.7149(6) _cell_measurement_reflns_used 9897 _cell_measurement_temperature 100(1) _cell_measurement_theta_max 66.62 _cell_measurement_theta_min 3.09 _cell_volume 1409.72(5) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX3' _computing_data_reduction 'Bruker SAINT' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 100(1) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker VENTURE PHOTON100 CMOS' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0492 _diffrn_reflns_av_unetI/netI 0.0217 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_number 25459 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 66.758 _diffrn_reflns_theta_max 66.758 _diffrn_reflns_theta_min 3.092 _exptl_absorpt_coefficient_mu 0.733 _exptl_absorpt_correction_T_max 0.9528 _exptl_absorpt_correction_T_min 0.8954 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Bruker APEX3' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.387 _exptl_crystal_description plate _exptl_crystal_F_000 624 _exptl_crystal_size_max 0.070 _exptl_crystal_size_mid 0.050 _exptl_crystal_size_min 0.040 _refine_diff_density_max 0.201 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.051 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 195 _refine_ls_number_reflns 2486 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.118 _refine_ls_R_factor_all 0.0525 _refine_ls_R_factor_gt 0.0457 _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^)+(0.0266P)^2^+1.6278P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0992 _refine_ls_wR_factor_ref 0.1019 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2237 _reflns_number_total 2486 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01518d2.cif _cod_data_source_block 5 _cod_depositor_comments 'Adding full bibliography for 7158328--7158329.cif.' _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7158328 _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 0.956 _shelx_estimated_absorpt_t_max 0.974 _shelx_res_file ; TITL cu_v1103_GuillotICMMO.res in P2(1)/c shelx.res created by SHELXL-2018/3 at 09:55:14 on 28-May-2021 CELL 1.54178 6.5607 7.5167 28.7149 90.000 95.426 90.000 ZERR 4.00 0.0001 0.0002 0.0006 0.000 0.001 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O DISP O 0.04946 0.03229 280.59 DISP N 0.03112 0.01806 156.90 DISP C 0.01788 0.00907 78.80 DISP H 0.00000 0.00000 0.64 UNIT 72 72 8 8 MERG 2 FMAP 2 PLAN 20 SIZE 0.040 0.050 0.070 ACTA 164.00 BOND $H LIST 6 L.S. 10 TEMP -173.00 WGHT 0.026600 1.627800 FVAR 0.25302 C1 1 0.620877 0.336371 0.427801 11.00000 0.01618 0.01347 = 0.01761 -0.00046 0.00174 -0.00100 AFIX 13 H1 2 0.754282 0.305536 0.415620 11.00000 -1.20000 AFIX 0 C2 1 0.464543 0.367913 0.386352 11.00000 0.01765 0.01563 = 0.01614 0.00047 0.00088 -0.00280 AFIX 13 H2 2 0.467451 0.272294 0.362211 11.00000 -1.20000 AFIX 0 C3 1 0.477103 0.559595 0.364539 11.00000 0.01472 0.01449 = 0.01398 -0.00179 0.00238 0.00102 C4 1 0.649389 0.676295 0.386467 11.00000 0.01498 0.01338 = 0.01575 -0.00243 0.00483 0.00252 C5 1 0.725374 0.644181 0.433108 11.00000 0.01597 0.01424 = 0.01635 -0.00047 0.00382 0.00188 C6 1 0.265373 0.602132 0.382482 11.00000 0.01376 0.02275 = 0.02057 -0.00386 0.00309 0.00083 AFIX 23 H00L 2 0.273351 0.689049 0.408494 11.00000 -1.20000 H6 2 0.159576 0.637729 0.357332 11.00000 -1.20000 AFIX 0 C7 1 0.244833 0.407898 0.398545 11.00000 0.01653 0.02950 = 0.02312 0.00617 0.00186 -0.00122 AFIX 23 H00D 2 0.138119 0.339954 0.379412 11.00000 -1.20000 H00F 2 0.227537 0.395990 0.432281 11.00000 -1.20000 AFIX 0 C8 1 0.564182 0.187023 0.459513 11.00000 0.01463 0.01507 = 0.01869 -0.00108 0.00293 0.00097 C9 1 0.866218 0.761988 0.455994 11.00000 0.01917 0.01845 = 0.01824 -0.00324 -0.00059 0.00176 AFIX 43 H9 2 0.916102 0.741113 0.487665 11.00000 -1.20000 AFIX 0 C10 1 0.933316 0.908987 0.432688 11.00000 0.01620 0.01626 = 0.02374 -0.00629 0.00189 0.00009 AFIX 43 H10 2 1.027274 0.989660 0.448569 11.00000 -1.20000 AFIX 0 C11 1 0.863612 0.938740 0.386176 11.00000 0.01971 0.01403 = 0.02437 -0.00033 0.00868 -0.00009 AFIX 43 H11 2 0.912011 1.037899 0.369913 11.00000 -1.20000 AFIX 0 C12 1 0.722394 0.822195 0.363607 11.00000 0.01830 0.01783 = 0.01546 0.00118 0.00393 0.00301 AFIX 43 H12 2 0.674815 0.842984 0.331793 11.00000 -1.20000 AFIX 0 C13 1 0.611036 0.505494 0.286856 11.00000 0.01834 0.00912 = 0.01783 -0.00300 0.00172 -0.00334 C14 1 0.789524 0.420300 0.305952 11.00000 0.01942 0.01549 = 0.01700 -0.00064 0.00103 -0.00043 AFIX 43 H14 2 0.811345 0.401833 0.338774 11.00000 -1.20000 AFIX 0 C15 1 0.934504 0.362783 0.277231 11.00000 0.01724 0.01750 = 0.02601 -0.00320 0.00261 -0.00021 AFIX 43 H15 2 1.054699 0.304848 0.290650 11.00000 -1.20000 AFIX 0 C16 1 0.907121 0.388316 0.229377 11.00000 0.02414 0.01959 = 0.02350 -0.00633 0.01089 -0.00333 AFIX 43 H16 2 1.006410 0.347275 0.209863 11.00000 -1.20000 AFIX 0 C17 1 0.731482 0.475218 0.210329 11.00000 0.03072 0.01783 = 0.01588 -0.00188 0.00376 -0.00579 AFIX 43 H17 2 0.711667 0.494671 0.177524 11.00000 -1.20000 AFIX 0 C18 1 0.585696 0.533543 0.238380 11.00000 0.02254 0.01392 = 0.01680 0.00008 0.00068 -0.00057 AFIX 43 H18 2 0.467089 0.593234 0.224745 11.00000 -1.20000 AFIX 2 N1 3 0.650362 0.497000 0.455901 11.00000 0.02875 0.01504 = 0.01232 0.00017 -0.00168 -0.00275 H101 2 0.710317 0.475601 0.484469 11.00000 -1.20000 N2 3 0.458288 0.558543 0.313838 11.00000 0.01592 0.01798 = 0.01323 0.00027 -0.00013 0.00398 H102 2 0.362416 0.626412 0.300077 11.00000 -1.20000 AFIX 0 O1 4 0.446486 0.064848 0.438653 11.00000 0.02376 0.01617 = 0.02019 0.00260 -0.00160 -0.00539 AFIX 148 H100 2 0.418236 -0.020946 0.460046 11.00000 -1.50000 AFIX 0 O2 4 0.630250 0.183414 0.500777 11.00000 0.02398 0.01754 = 0.01567 0.00141 -0.00021 -0.00290 HKLF 4 REM cu_v1103_GuillotICMMO.res in P2(1)/c REM wR2 = 0.1019, GooF = S = 1.118, Restrained GooF = 1.118 for all data REM R1 = 0.0457 for 2237 Fo > 4sig(Fo) and 0.0525 for all 2486 data REM 195 parameters refined using 0 restraints END WGHT 0.0266 1.6270 REM Highest difference peak 0.201, deepest hole -0.245, 1-sigma level 0.051 Q1 1 0.3633 0.5976 0.3689 11.00000 0.05 0.20 Q2 1 0.2096 0.6868 0.3629 11.00000 0.05 0.19 Q3 1 0.9649 0.7889 0.4400 11.00000 0.05 0.18 Q4 1 0.7418 0.5111 0.2957 11.00000 0.05 0.17 Q5 1 0.2679 0.5091 0.4103 11.00000 0.05 0.17 Q6 1 1.1097 0.3556 0.2811 11.00000 0.05 0.16 Q7 1 1.0696 0.2681 0.3087 11.00000 0.05 0.16 Q8 1 0.7428 0.7375 0.4522 11.00000 0.05 0.15 Q9 1 1.2364 0.3412 0.3083 11.00000 0.05 0.15 Q10 1 0.8759 0.6388 0.4314 11.00000 0.05 0.15 Q11 1 0.0123 0.6328 0.4163 11.00000 0.05 0.15 Q12 1 0.7708 0.2594 0.4137 11.00000 0.05 0.14 Q13 1 0.5652 0.6183 0.3738 11.00000 0.05 0.14 Q14 1 1.0255 1.1076 0.3697 11.00000 0.05 0.14 Q15 1 0.0357 0.7209 0.3584 11.00000 0.05 0.14 Q16 1 1.0343 0.8138 0.4693 11.00000 0.05 0.14 Q17 1 0.5021 0.4081 0.4495 11.00000 0.05 0.14 Q18 1 1.0054 0.0941 0.2987 11.00000 0.05 0.13 Q19 1 0.3103 0.1261 0.4514 11.00000 0.05 0.13 Q20 1 0.3610 0.3731 0.3958 11.00000 0.05 0.13 ; _shelx_res_checksum 90895 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 C1 C 0.6209(3) 0.3364(2) 0.42780(7) 0.0157(4) Uani 1 1 d . . . . . H1 H 0.754282 0.305536 0.415620 0.019 Uiso 1 1 calc R U . . . C2 C 0.4645(3) 0.3679(3) 0.38635(7) 0.0165(4) Uani 1 1 d . . . . . H2 H 0.467451 0.272294 0.362211 0.020 Uiso 1 1 calc R U . . . C3 C 0.4771(3) 0.5596(2) 0.36454(6) 0.0143(4) Uani 1 1 d . . . . . C4 C 0.6494(3) 0.6763(2) 0.38647(7) 0.0145(4) Uani 1 1 d . . . . . C5 C 0.7254(3) 0.6442(2) 0.43311(7) 0.0154(4) Uani 1 1 d . . . . . C6 C 0.2654(3) 0.6021(3) 0.38248(7) 0.0189(4) Uani 1 1 d . . . . . H00L H 0.273351 0.689049 0.408494 0.023 Uiso 1 1 calc R U . . . H6 H 0.159576 0.637729 0.357332 0.023 Uiso 1 1 calc R U . . . C7 C 0.2448(3) 0.4079(3) 0.39855(7) 0.0230(5) Uani 1 1 d . . . . . H00D H 0.138119 0.339954 0.379412 0.028 Uiso 1 1 calc R U . . . H00F H 0.227537 0.395990 0.432281 0.028 Uiso 1 1 calc R U . . . C8 C 0.5642(3) 0.1870(3) 0.45951(7) 0.0160(4) Uani 1 1 d . . . . . C9 C 0.8662(3) 0.7620(3) 0.45599(7) 0.0188(4) Uani 1 1 d . . . . . H9 H 0.916102 0.741113 0.487665 0.023 Uiso 1 1 calc R U . . . C10 C 0.9333(3) 0.9090(3) 0.43269(7) 0.0187(4) Uani 1 1 d . . . . . H10 H 1.027274 0.989660 0.448569 0.022 Uiso 1 1 calc R U . . . C11 C 0.8636(3) 0.9387(3) 0.38618(7) 0.0189(4) Uani 1 1 d . . . . . H11 H 0.912011 1.037899 0.369913 0.023 Uiso 1 1 calc R U . . . C12 C 0.7224(3) 0.8222(3) 0.36361(7) 0.0170(4) Uani 1 1 d . . . . . H12 H 0.674815 0.842984 0.331793 0.020 Uiso 1 1 calc R U . . . C13 C 0.6110(3) 0.5055(2) 0.28686(7) 0.0151(4) Uani 1 1 d . . . . . C14 C 0.7895(3) 0.4203(3) 0.30595(7) 0.0173(4) Uani 1 1 d . . . . . H14 H 0.811345 0.401833 0.338774 0.021 Uiso 1 1 calc R U . . . C15 C 0.9345(3) 0.3628(3) 0.27723(7) 0.0202(4) Uani 1 1 d . . . . . H15 H 1.054699 0.304848 0.290650 0.024 Uiso 1 1 calc R U . . . C16 C 0.9071(3) 0.3883(3) 0.22938(7) 0.0219(5) Uani 1 1 d . . . . . H16 H 1.006410 0.347275 0.209863 0.026 Uiso 1 1 calc R U . . . C17 C 0.7315(3) 0.4752(3) 0.21033(7) 0.0214(4) Uani 1 1 d . . . . . H17 H 0.711667 0.494671 0.177524 0.026 Uiso 1 1 calc R U . . . C18 C 0.5857(3) 0.5335(3) 0.23838(7) 0.0178(4) Uani 1 1 d . . . . . H18 H 0.467089 0.593234 0.224745 0.021 Uiso 1 1 calc R U . . . N1 N 0.6504(3) 0.4970(2) 0.45590(6) 0.019 Uani 1 1 d . . . . . H101 H 0.710(3) 0.476(3) 0.4845(8) 0.023 Uiso 1 1 d . U . . . N2 N 0.4583(2) 0.5585(2) 0.31384(5) 0.016 Uani 1 1 d . . . . . H102 H 0.362(3) 0.626(3) 0.3001(7) 0.019 Uiso 1 1 d . U . . . O1 O 0.4465(2) 0.06485(18) 0.43865(5) 0.0203(3) Uani 1 1 d . . . . . H100 H 0.418(3) -0.021(3) 0.4600(6) 0.030 Uiso 1 1 calc R U . . . O2 O 0.6303(2) 0.18341(18) 0.50078(5) 0.0192(3) Uani 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 C1 0.0162(10) 0.0135(10) 0.0176(10) -0.0005(7) 0.0017(8) -0.0010(7) C2 0.0177(10) 0.0156(10) 0.0161(10) 0.0005(8) 0.0009(8) -0.0028(8) C3 0.0147(10) 0.0145(9) 0.0140(9) -0.0018(7) 0.0024(7) 0.0010(7) C4 0.0150(10) 0.0134(9) 0.0157(9) -0.0024(7) 0.0048(7) 0.0025(7) C5 0.0160(10) 0.0142(10) 0.0163(9) -0.0005(7) 0.0038(7) 0.0019(7) C6 0.0138(10) 0.0227(11) 0.0206(10) -0.0039(8) 0.0031(8) 0.0008(8) C7 0.0165(10) 0.0295(12) 0.0231(11) 0.0062(9) 0.0019(8) -0.0012(9) C8 0.0146(10) 0.0151(9) 0.0187(10) -0.0011(7) 0.0029(8) 0.0010(7) C9 0.0192(10) 0.0184(10) 0.0182(10) -0.0032(8) -0.0006(8) 0.0018(8) C10 0.0162(10) 0.0163(10) 0.0237(11) -0.0063(8) 0.0019(8) 0.0001(8) C11 0.0197(10) 0.0140(10) 0.0244(11) -0.0003(8) 0.0087(8) -0.0001(8) C12 0.0183(10) 0.0178(10) 0.0155(9) 0.0012(7) 0.0039(8) 0.0030(8) C13 0.0183(10) 0.0091(9) 0.0178(10) -0.0030(7) 0.0017(8) -0.0033(7) C14 0.0194(10) 0.0155(10) 0.0170(10) -0.0006(7) 0.0010(8) -0.0004(8) C15 0.0172(10) 0.0175(10) 0.0260(11) -0.0032(8) 0.0026(8) -0.0002(8) C16 0.0241(11) 0.0196(11) 0.0235(11) -0.0063(8) 0.0109(9) -0.0033(8) C17 0.0307(12) 0.0178(10) 0.0159(10) -0.0019(8) 0.0038(8) -0.0058(9) C18 0.0225(11) 0.0139(10) 0.0168(10) 0.0001(8) 0.0007(8) -0.0006(8) N1 0.029 0.015 0.012 0.000 -0.002 -0.003 N2 0.016 0.018 0.013 0.000 0.000 0.004 O1 0.0238(8) 0.0162(7) 0.0202(7) 0.0026(6) -0.0016(6) -0.0054(6) O2 0.0240(8) 0.0175(7) 0.0157(7) 0.0014(5) -0.0002(6) -0.0029(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0179 0.0091 '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 0.0311 0.0181 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0495 0.0323 '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 N1 C1 C8 108.01(15) . . ? N1 C1 C2 110.52(16) . . ? C8 C1 C2 113.71(16) . . ? N1 C1 H1 108.1 . . ? C8 C1 H1 108.1 . . ? C2 C1 H1 108.1 . . ? C1 C2 C7 115.43(16) . . ? C1 C2 C3 113.48(15) . . ? C7 C2 C3 89.84(15) . . ? C1 C2 H2 112.1 . . ? C7 C2 H2 112.1 . . ? C3 C2 H2 112.1 . . ? N2 C3 C4 114.13(16) . . ? N2 C3 C6 109.82(15) . . ? C4 C3 C6 113.30(15) . . ? N2 C3 C2 113.04(15) . . ? C4 C3 C2 115.33(15) . . ? C6 C3 C2 88.54(14) . . ? C12 C4 C5 118.67(18) . . ? C12 C4 C3 122.49(17) . . ? C5 C4 C3 118.61(17) . . ? C9 C5 N1 121.82(17) . . ? C9 C5 C4 119.89(18) . . ? N1 C5 C4 118.24(17) . . ? C7 C6 C3 90.60(15) . . ? C7 C6 H00L 113.5 . . ? C3 C6 H00L 113.5 . . ? C7 C6 H6 113.5 . . ? C3 C6 H6 113.5 . . ? H00L C6 H6 110.8 . . ? C6 C7 C2 90.38(15) . . ? C6 C7 H00D 113.6 . . ? C2 C7 H00D 113.6 . . ? C6 C7 H00F 113.6 . . ? C2 C7 H00F 113.6 . . ? H00D C7 H00F 110.8 . . ? O2 C8 O1 124.61(18) . . ? O2 C8 C1 120.97(17) . . ? O1 C8 C1 114.40(16) . . ? C10 C9 C5 120.28(18) . . ? C10 C9 H9 119.9 . . ? C5 C9 H9 119.9 . . ? C9 C10 C11 120.17(18) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C10 C11 C12 119.43(18) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C4 C12 C11 121.51(18) . . ? C4 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? N2 C13 C14 122.43(18) . . ? N2 C13 C18 119.27(17) . . ? C14 C13 C18 118.28(18) . . ? C15 C14 C13 120.35(18) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C16 C15 C14 121.09(19) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C15 C16 C17 118.76(19) . . ? C15 C16 H16 120.6 . . ? C17 C16 H16 120.6 . . ? C18 C17 C16 120.95(19) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C17 C18 C13 120.56(19) . . ? C17 C18 H18 119.7 . . ? C13 C18 H18 119.7 . . ? C5 N1 C1 115.54(15) . . ? C5 N1 H101 115.5(15) . . ? C1 N1 H101 112.6(15) . . ? C13 N2 C3 124.56(16) . . ? C13 N2 H102 116.3(14) . . ? C3 N2 H102 116.1(14) . . ? C8 O1 H100 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 C1 N1 1.455(2) . ? C1 C8 1.514(3) . ? C1 C2 1.515(3) . ? C1 H1 1.0000 . ? C2 C7 1.545(3) . ? C2 C3 1.576(3) . ? C2 H2 1.0000 . ? C3 N2 1.449(2) . ? C3 C4 1.520(3) . ? C3 C6 1.560(3) . ? C4 C12 1.387(3) . ? C4 C5 1.405(3) . ? C5 C9 1.398(3) . ? C5 N1 1.398(2) . ? C6 C7 1.541(3) . ? C6 H00L 0.9900 . ? C6 H6 0.9900 . ? C7 H00D 0.9900 . ? C7 H00F 0.9900 . ? C8 O2 1.223(2) . ? C8 O1 1.308(2) . ? C9 C10 1.385(3) . ? C9 H9 0.9500 . ? C10 C11 1.388(3) . ? C10 H10 0.9500 . ? C11 C12 1.390(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 N2 1.382(2) . ? C13 C14 1.400(3) . ? C13 C18 1.402(3) . ? C14 C15 1.386(3) . ? C14 H14 0.9500 . ? C15 C16 1.382(3) . ? C15 H15 0.9500 . ? C16 C17 1.391(3) . ? C16 H16 0.9500 . ? C17 C18 1.379(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? N1 H101 0.89(2) . ? N2 H102 0.87(2) . ? O1 H100 0.92(3) . ?