#------------------------------------------------------------------------------ #$Date: 2011-06-22 01:15:01 +0300 (Wed, 22 Jun 2011) $ #$Revision: 21330 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/7015730.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_7015730 loop_ _publ_author_name 'Godau, Tom' 'Bleifu\&s, Sascha M' 'M\"uller, Astrid L' 'Roth, Thomas' 'Hoffmann, Susanne' 'Heinemann, Frank W.' 'Burzlaff, Nicolai' _publ_section_title ; Cu(i) catalysed cyclopropanation with enantiopure scorpionate type ligands derived from (+)-camphor or (-)-menthone. ; _journal_issue 24 _journal_name_full 'Dalton transactions (Cambridge, England : 2003)' _journal_page_first 6547 _journal_page_last 6554 _journal_volume 40 _journal_year 2011 _chemical_absolute_configuration rm _chemical_compound_source 'synthesis as described' _chemical_formula_moiety 'C27 H36 N6' _chemical_formula_sum 'C27 H36 N6' _chemical_formula_weight 444.62 _chemical_name_systematic ; ? ; _space_group_IT_number 5 _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 5 _symmetry_space_group_name_Hall 'C 2y' _symmetry_space_group_name_H-M 'C 1 2 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2009-11-22T22:48:09-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90 _cell_angle_beta 133.701(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 25.4805(12) _cell_length_b 7.7565(5) _cell_length_c 17.8684(7) _cell_measurement_reflns_used 136 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 20 _cell_measurement_theta_min 6 _cell_measurement_wavelength 0.71073 _cell_volume 2553.1(3) _computing_cell_refinement 'EVALCCD (Duisenberg, 2003)' _computing_data_collection 'COLLECT (Bruker-Nonius, 2002)' _computing_data_reduction 'EVALCCD (Duisenberg, 2003)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 9 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_method ; \f- and \w-rotations with 2.00 \% and 100 sec per frame ; _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_unetI/netI 0.0263 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 39319 _diffrn_reflns_theta_full 28.52 _diffrn_reflns_theta_max 28.52 _diffrn_reflns_theta_min 2.85 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.952022 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker-AXS, 2002' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.157 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 960 _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.241 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.048 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 298 _refine_ls_number_reflns 3470 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.066 _refine_ls_R_factor_all 0.0541 _refine_ls_R_factor_gt 0.0423 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0699P)^2^+0.6097P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1074 _refine_ls_wR_factor_ref 0.1141 _reflns_number_gt 2971 _reflns_number_total 3470 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file c1dt10032g.txt _[local]_cod_data_source_block tgbu03 _[local]_cod_cif_authors_sg_H-M 'C 2' _cod_original_cell_volume 2553.1(2) _cod_database_code 7015730 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.08535(10) 0.6440(2) 0.15127(15) 0.0176(4) Uani 1 1 d . . . H1 H 0.0698 0.6818 0.0861 0.021 Uiso 1 1 calc R . . C2 C 0.07353(10) 0.4524(3) 0.14540(16) 0.0209(4) Uani 1 1 d . . . C3 C 0.05574(14) 0.1973(3) 0.1677(2) 0.0406(6) Uani 1 1 d . . . H3 H 0.0422 0.1061 0.1852 0.049 Uiso 1 1 calc R . . C4 C 0.08445(14) 0.1792(3) 0.1274(2) 0.0400(6) Uani 1 1 d . . . H4 H 0.0945 0.0764 0.1126 0.048 Uiso 1 1 calc R . . C5 C 0.12979(14) 0.3904(4) 0.0744(2) 0.0358(5) Uani 1 1 d . . . H5A H 0.0935 0.4359 0.0055 0.054 Uiso 1 1 calc R . . H5B H 0.1515 0.29 0.0737 0.054 Uiso 1 1 calc R . . H5C H 0.1665 0.4761 0.1191 0.054 Uiso 1 1 calc R . . C11 C 0.21329(11) 0.5828(3) 0.32225(16) 0.0238(4) Uani 1 1 d . . . H11 H 0.2065 0.4767 0.3388 0.029 Uiso 1 1 calc R . . C12 C 0.27625(11) 0.6754(3) 0.37996(15) 0.0230(4) Uani 1 1 d . . . C13 C 0.25825(10) 0.8232(3) 0.32166(15) 0.0213(4) Uani 1 1 d . . . C14 C 0.32505(12) 0.9321(3) 0.37810(18) 0.0338(5) Uani 1 1 d . . . C15 C 0.37374(14) 0.8234(5) 0.3721(2) 0.0529(8) Uani 1 1 d . . . H15A H 0.347 0.7916 0.3011 0.064 Uiso 1 1 calc R . . H15B H 0.4166 0.888 0.3997 0.064 Uiso 1 1 calc R . . C16 C 0.39493(14) 0.6622(5) 0.4383(3) 0.0529(8) Uani 1 1 d . . . H16A H 0.4471 0.6552 0.4962 0.064 Uiso 1 1 calc R . . H16B H 0.378 0.5579 0.3972 0.064 Uiso 1 1 calc R . . C17 C 0.35639(12) 0.6892(4) 0.47592(18) 0.0340(5) Uani 1 1 d . . . H17 H 0.3741 0.6187 0.5351 0.041 Uiso 1 1 calc R . . C18 C 0.36225(13) 0.8883(4) 0.49219(18) 0.0334(5) Uani 1 1 d . . . C19 C 0.32023(16) 0.9541(5) 0.5181(2) 0.0531(8) Uani 1 1 d . . . H19A H 0.271 0.9138 0.467 0.08 Uiso 1 1 calc R . . H19B H 0.3206 1.0779 0.5186 0.08 Uiso 1 1 calc R . . H19C H 0.3425 0.9123 0.5851 0.08 Uiso 1 1 calc R . . C20 C 0.44032(15) 0.9558(5) 0.5755(2) 0.0526(8) Uani 1 1 d . . . H20A H 0.4683 0.9149 0.5614 0.079 Uiso 1 1 calc R . . H20B H 0.4616 0.9152 0.6422 0.079 Uiso 1 1 calc R . . H20C H 0.4399 1.0796 0.575 0.079 Uiso 1 1 calc R . . C21 C 0.31333(18) 1.1182(4) 0.3458(3) 0.0662(11) Uani 1 1 d . . . H21A H 0.3594 1.1751 0.3869 0.099 Uiso 1 1 calc R . . H21B H 0.2849 1.1737 0.356 0.099 Uiso 1 1 calc R . . H21C H 0.2882 1.1246 0.2741 0.099 Uiso 1 1 calc R . . C31 C 0.05897(10) 0.7616(3) 0.25510(14) 0.0211(4) Uani 1 1 d . . . H31 H 0.1037 0.745 0.3222 0.025 Uiso 1 1 calc R . . C32 C -0.00412(10) 0.8150(3) 0.22606(15) 0.0207(4) Uani 1 1 d . . . C33 C -0.05515(10) 0.8166(3) 0.11758(15) 0.0197(4) Uani 1 1 d . . . C34 C -0.12689(11) 0.8787(3) 0.07740(16) 0.0247(4) Uani 1 1 d . . . C35 C -0.11339(14) 1.0730(3) 0.1084(2) 0.0355(5) Uani 1 1 d . . . H35A H -0.1582 1.1294 0.0789 0.043 Uiso 1 1 calc R . . H35B H -0.0935 1.132 0.0848 0.043 Uiso 1 1 calc R . . C36 C -0.05788(15) 1.0721(4) 0.2290(2) 0.0394(6) Uani 1 1 d . . . H36A H -0.0135 1.1318 0.2591 0.047 Uiso 1 1 calc R . . H36B H -0.0783 1.1255 0.2533 0.047 Uiso 1 1 calc R . . C37 C -0.04373(12) 0.8773(3) 0.25582(17) 0.0309(5) Uani 1 1 d . . . H37 H -0.0217 0.8466 0.3257 0.037 Uiso 1 1 calc R . . C38 C -0.12057(12) 0.7971(4) 0.16420(19) 0.0330(6) Uani 1 1 d . . . C39 C -0.12091(16) 0.5998(4) 0.1638(3) 0.0504(8) Uani 1 1 d . . . H39A H -0.0839 0.5582 0.167 0.076 Uiso 1 1 calc R . . H39B H -0.1674 0.559 0.1015 0.076 Uiso 1 1 calc R . . H39C H -0.1116 0.5583 0.2227 0.076 Uiso 1 1 calc R . . C40 C -0.18000(14) 0.8623(5) 0.1595(2) 0.0521(8) Uani 1 1 d . . . H40A H -0.18 0.9861 0.16 0.078 Uiso 1 1 calc R . . H40B H -0.1705 0.82 0.2184 0.078 Uiso 1 1 calc R . . H40C H -0.2265 0.8215 0.0971 0.078 Uiso 1 1 calc R . . C41 C -0.19387(11) 0.8392(5) -0.03453(18) 0.0414(7) Uani 1 1 d . . . H41A H -0.2359 0.8851 -0.0513 0.062 Uiso 1 1 calc R . . H41B H -0.199 0.7166 -0.0448 0.062 Uiso 1 1 calc R . . H41C H -0.1892 0.8908 -0.0785 0.062 Uiso 1 1 calc R . . N1 N 0.04882(10) 0.3699(2) 0.17990(16) 0.0303(4) Uani 1 1 d . . . N2 N 0.09605(10) 0.3436(2) 0.11258(14) 0.0269(4) Uani 1 1 d . . . N11 N 0.18947(9) 0.8300(2) 0.23281(13) 0.0221(4) Uani 1 1 d . . . N12 N 0.16214(8) 0.6793(2) 0.23464(12) 0.0179(3) Uani 1 1 d . . . N31 N -0.02864(8) 0.7692(2) 0.07845(12) 0.0203(3) Uani 1 1 d . . . N32 N 0.04295(8) 0.7375(2) 0.16538(12) 0.0175(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 0.0144(8) 0.0166(9) 0.0189(9) 0.0004(7) 0.0104(8) 0.0003(7) C2 0.0131(9) 0.0185(9) 0.0245(10) -0.0009(8) 0.0104(8) -0.0003(7) C3 0.0420(14) 0.0206(11) 0.0585(17) 0.0040(11) 0.0344(14) -0.0043(11) C4 0.0394(14) 0.0173(11) 0.0567(17) -0.0025(11) 0.0308(14) 0.0014(10) C5 0.0368(13) 0.0344(13) 0.0460(14) -0.0049(11) 0.0323(12) 0.0033(10) C11 0.0192(9) 0.0223(10) 0.0238(10) 0.0060(8) 0.0126(8) 0.0021(8) C12 0.0173(9) 0.0257(10) 0.0215(9) 0.0005(8) 0.0117(8) -0.0003(8) C13 0.0209(9) 0.0239(9) 0.0223(9) -0.0039(8) 0.0161(8) -0.0056(8) C14 0.0243(11) 0.0404(14) 0.0280(11) -0.0060(10) 0.0148(9) -0.0152(10) C15 0.0321(13) 0.087(2) 0.0516(16) -0.0193(18) 0.0336(13) -0.0223(15) C16 0.0227(12) 0.063(2) 0.0611(18) -0.0158(16) 0.0243(13) -0.0018(12) C17 0.0165(10) 0.0409(13) 0.0266(11) 0.0002(10) 0.0080(9) -0.0028(10) C18 0.0229(11) 0.0410(14) 0.0244(11) -0.0080(10) 0.0118(10) -0.0071(10) C19 0.0434(15) 0.074(2) 0.0348(14) -0.0254(15) 0.0242(13) -0.0081(16) C20 0.0300(13) 0.0560(18) 0.0388(14) -0.0164(14) 0.0113(12) -0.0169(14) C21 0.0503(18) 0.0491(19) 0.0524(18) 0.0045(15) 0.0177(15) -0.0306(15) C31 0.0188(9) 0.0218(9) 0.0163(8) 0.0019(8) 0.0098(8) 0.0019(8) C32 0.0206(9) 0.0210(9) 0.0198(9) 0.0019(8) 0.0136(8) 0.0014(8) C33 0.0174(9) 0.0186(9) 0.0204(9) 0.0017(8) 0.0120(8) 0.0008(7) C34 0.0188(9) 0.0337(11) 0.0220(10) 0.0046(9) 0.0143(9) 0.0070(8) C35 0.0367(12) 0.0325(13) 0.0397(13) 0.0107(10) 0.0273(11) 0.0162(10) C36 0.0413(14) 0.0395(15) 0.0417(14) -0.0065(12) 0.0303(13) 0.0084(12) C37 0.0287(11) 0.0457(14) 0.0237(10) 0.0067(10) 0.0202(10) 0.0095(10) C38 0.0248(11) 0.0470(16) 0.0341(11) 0.0123(11) 0.0229(10) 0.0085(10) C39 0.0389(15) 0.0492(17) 0.0664(19) 0.0170(15) 0.0376(15) -0.0018(13) C40 0.0358(14) 0.087(2) 0.0509(15) 0.0186(16) 0.0364(13) 0.0158(15) C41 0.0179(10) 0.0666(19) 0.0289(11) -0.0025(13) 0.0121(10) 0.0101(12) N1 0.0271(9) 0.0231(10) 0.0417(11) 0.0016(8) 0.0241(9) -0.0030(8) N2 0.0248(9) 0.0182(9) 0.0356(10) -0.0031(8) 0.0201(9) 0.0008(7) N11 0.0208(8) 0.0218(8) 0.0204(8) -0.0010(7) 0.0130(7) -0.0060(7) N12 0.0152(7) 0.0168(7) 0.0185(8) 0.0011(7) 0.0104(7) -0.0012(6) N31 0.0151(7) 0.0228(8) 0.0185(7) 0.0004(7) 0.0098(6) 0.0031(7) N32 0.0151(7) 0.0171(8) 0.0170(7) 0.0009(6) 0.0098(7) 0.0012(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 '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 N12 C1 N32 111.31(15) . . ? N12 C1 C2 108.76(16) . . ? N32 C1 C2 111.46(16) . . ? N12 C1 H1 108.4 . . ? N32 C1 H1 108.4 . . ? C2 C1 H1 108.4 . . ? N1 C2 N2 112.45(19) . . ? N1 C2 C1 125.92(19) . . ? N2 C2 C1 121.25(18) . . ? C4 C3 N1 111.2(2) . . ? C4 C3 H3 124.4 . . ? N1 C3 H3 124.4 . . ? C3 C4 N2 106.0(2) . . ? C3 C4 H4 127 . . ? N2 C4 H4 127 . . ? N2 C5 H5A 109.5 . . ? N2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C12 C11 N12 105.55(18) . . ? C12 C11 H11 127.2 . . ? N12 C11 H11 127.2 . . ? C11 C12 C13 105.03(17) . . ? C11 C12 C17 148.8(2) . . ? C13 C12 C17 106.14(19) . . ? N11 C13 C12 114.10(18) . . ? N11 C13 C14 136.9(2) . . ? C12 C13 C14 108.98(18) . . ? C13 C14 C21 116.7(2) . . ? C13 C14 C15 103.6(2) . . ? C21 C14 C15 116.6(3) . . ? C13 C14 C18 97.85(18) . . ? C21 C14 C18 118.9(2) . . ? C15 C14 C18 100.1(2) . . ? C16 C15 C14 105.0(2) . . ? C16 C15 H15A 110.7 . . ? C14 C15 H15A 110.7 . . ? C16 C15 H15B 110.7 . . ? C14 C15 H15B 110.7 . . ? H15A C15 H15B 108.8 . . ? C15 C16 C17 103.5(2) . . ? C15 C16 H16A 111.1 . . ? C17 C16 H16A 111.1 . . ? C15 C16 H16B 111.1 . . ? C17 C16 H16B 111.1 . . ? H16A C16 H16B 109 . . ? C12 C17 C16 105.3(2) . . ? C12 C17 C18 99.3(2) . . ? C16 C17 C18 102.0(2) . . ? C12 C17 H17 116 . . ? C16 C17 H17 116 . . ? C18 C17 H17 116 . . ? C19 C18 C20 107.7(2) . . ? C19 C18 C17 113.1(2) . . ? C20 C18 C17 114.3(2) . . ? C19 C18 C14 113.6(2) . . ? C20 C18 C14 113.5(2) . . ? C17 C18 C14 94.45(19) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C14 C21 H21A 109.5 . . ? C14 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C14 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N32 C31 C32 106.02(16) . . ? N32 C31 H31 127 . . ? C32 C31 H31 127 . . ? C31 C32 C33 104.55(17) . . ? C31 C32 C37 149.31(19) . . ? C33 C32 C37 106.10(16) . . ? N31 C33 C32 113.95(17) . . ? N31 C33 C34 137.24(18) . . ? C32 C33 C34 108.79(16) . . ? C33 C34 C41 116.96(18) . . ? C33 C34 C35 104.04(18) . . ? C41 C34 C35 115.8(2) . . ? C33 C34 C38 97.86(16) . . ? C41 C34 C38 118.3(2) . . ? C35 C34 C38 101.01(18) . . ? C34 C35 C36 104.68(19) . . ? C34 C35 H35A 110.8 . . ? C36 C35 H35A 110.8 . . ? C34 C35 H35B 110.8 . . ? C36 C35 H35B 110.8 . . ? H35A C35 H35B 108.9 . . ? C37 C36 C35 103.1(2) . . ? C37 C36 H36A 111.1 . . ? C35 C36 H36A 111.1 . . ? C37 C36 H36B 111.1 . . ? C35 C36 H36B 111.1 . . ? H36A C36 H36B 109.1 . . ? C32 C37 C36 105.85(19) . . ? C32 C37 C38 99.28(17) . . ? C36 C37 C38 101.96(19) . . ? C32 C37 H37 115.9 . . ? C36 C37 H37 115.9 . . ? C38 C37 H37 115.9 . . ? C39 C38 C40 109.0(2) . . ? C39 C38 C37 113.5(2) . . ? C40 C38 C37 113.4(2) . . ? C39 C38 C34 113.6(2) . . ? C40 C38 C34 112.7(2) . . ? C37 C38 C34 94.17(17) . . ? C38 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C38 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C38 C40 H40A 109.5 . . ? C38 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C38 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C34 C41 H41A 109.5 . . ? C34 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C34 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C2 N1 C3 104.0(2) . . ? C2 N2 C4 106.34(19) . . ? C2 N2 C5 127.20(19) . . ? C4 N2 C5 126.4(2) . . ? C13 N11 N12 102.14(16) . . ? N11 N12 C11 113.18(15) . . ? N11 N12 C1 118.94(15) . . ? C11 N12 C1 127.78(17) . . ? C33 N31 N32 102.55(15) . . ? C31 N32 N31 112.91(15) . . ? C31 N32 C1 127.83(16) . . ? N31 N32 C1 117.17(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 C1 N12 1.447(2) . ? C1 N32 1.461(2) . ? C1 C2 1.505(3) . ? C1 H1 0.98 . ? C2 N1 1.312(3) . ? C2 N2 1.361(3) . ? C3 C4 1.342(4) . ? C3 N1 1.387(3) . ? C3 H3 0.93 . ? C4 N2 1.375(3) . ? C4 H4 0.93 . ? C5 N2 1.465(3) . ? C5 H5A 0.96 . ? C5 H5B 0.96 . ? C5 H5C 0.96 . ? C11 C12 1.366(3) . ? C11 N12 1.375(3) . ? C11 H11 0.93 . ? C12 C13 1.396(3) . ? C12 C17 1.511(3) . ? C13 N11 1.323(3) . ? C13 C14 1.502(3) . ? C14 C21 1.506(4) . ? C14 C15 1.564(4) . ? C14 C18 1.581(3) . ? C15 C16 1.541(5) . ? C15 H15A 0.97 . ? C15 H15B 0.97 . ? C16 C17 1.541(4) . ? C16 H16A 0.97 . ? C16 H16B 0.97 . ? C17 C18 1.559(4) . ? C17 H17 0.98 . ? C18 C19 1.519(4) . ? C18 C20 1.535(3) . ? C19 H19A 0.96 . ? C19 H19B 0.96 . ? C19 H19C 0.96 . ? C20 H20A 0.96 . ? C20 H20B 0.96 . ? C20 H20C 0.96 . ? C21 H21A 0.96 . ? C21 H21B 0.96 . ? C21 H21C 0.96 . ? C31 N32 1.367(3) . ? C31 C32 1.368(3) . ? C31 H31 0.93 . ? C32 C33 1.402(3) . ? C32 C37 1.509(3) . ? C33 N31 1.316(3) . ? C33 C34 1.509(3) . ? C34 C41 1.513(3) . ? C34 C35 1.559(3) . ? C34 C38 1.577(3) . ? C35 C36 1.560(4) . ? C35 H35A 0.97 . ? C35 H35B 0.97 . ? C36 C37 1.550(4) . ? C36 H36A 0.97 . ? C36 H36B 0.97 . ? C37 C38 1.572(3) . ? C37 H37 0.98 . ? C38 C39 1.531(4) . ? C38 C40 1.543(3) . ? C39 H39A 0.96 . ? C39 H39B 0.96 . ? C39 H39C 0.96 . ? C40 H40A 0.96 . ? C40 H40B 0.96 . ? C40 H40C 0.96 . ? C41 H41A 0.96 . ? C41 H41B 0.96 . ? C41 H41C 0.96 . ? N11 N12 1.373(2) . ? N31 N32 1.373(2) . ?