# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email hideto@chem.eng.osaka-u.ac.jp _publ_contact_author_name 'Hideto, Nakajima' loop_ _publ_author_name H.Nakajima M.Yasuda K.Chiba A.Baba data_b _database_code_depnum_ccdc_archive 'CCDC 764736' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '0.44(C35 H32 Ga N O3), 0.56(C35 H35 N O3)' _chemical_formula_sum 'C35 H33.68 Ga0.44 N O3' _chemical_formula_weight 545.29 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' Ga Ga 0.2307 1.6083 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 _symmetry_space_group_name_Hall '-p 2yn' loop_ _symmetry_equiv_pos_as_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' _cell_length_a 11.8141(10) _cell_length_b 15.4673(14) _cell_length_c 16.5096(16) _cell_angle_alpha 90.00 _cell_angle_beta 102.713(3) _cell_angle_gamma 90.00 _cell_volume 2942.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 22582 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 30.49 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.231 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1147 _exptl_absorpt_coefficient_mu 0.468 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.7997 _exptl_absorpt_correction_T_max 0.8533 _exptl_absorpt_process_details ; Higashi, T. (1999). Abscor - Empirical Absorption Correction based on Fourier Series Approximation. Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'imaging plate' _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10283 _diffrn_reflns_av_R_equivalents 0.0166 _diffrn_reflns_av_sigmaI/netI 0.0223 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5152 _reflns_number_gt 3691 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rigaku/RAPID Diffractometer Control' _computing_cell_refinement 'Rigaku/RAPID Diffractometer Control' _computing_data_reduction 'teXsan: PROCESS (MSC)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1999)' _computing_structure_solution 'PATTY (Bueskens, et al., 1994)' _computing_publication_material 'SHELXL-97 and modified' _computing_molecular_graphics 'Ortep-3 (Louis J. Farrugia, 1999)' # Carroll K. Johnson and M. N. Burnett, ORNL-6895, ORTEP-III(version 1.0.2), # A FORTRAN Thermal-Ellipsoid Plot Program, Oak Ridge National Labratory, # Oak Ridge, Tennessee. # Ortep-3 for Windows, Version 1.05 Louis J. Farrugia, _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1149P)^2^+0.2684P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5152 _refine_ls_number_parameters 419 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0758 _refine_ls_R_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.1881 _refine_ls_wR_factor_gt 0.1637 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 O1 O 1.18881(16) 0.82524(14) 0.30112(15) 0.1128(7) Uani 1 1 d . . . O2 O 0.86101(17) 0.99199(11) 0.43163(12) 0.0945(6) Uani 1 1 d . . . O3 O 0.99742(16) 1.08363(13) 0.15167(17) 0.1190(8) Uani 1 1 d . . . C1 C 0.78438(16) 0.71247(12) 0.14749(13) 0.0591(5) Uani 1 1 d . . . C2 C 0.71993(16) 0.72325(12) 0.20876(12) 0.0588(5) Uani 1 1 d . . . C3 C 0.64166(15) 0.79217(13) 0.20311(12) 0.0592(5) Uani 1 1 d . . . C4 C 0.63271(16) 0.85314(13) 0.13897(12) 0.0602(5) Uani 1 1 d . . . C5 C 0.69339(17) 0.83984(12) 0.07604(12) 0.0606(5) Uani 1 1 d . . . C6 C 0.76957(17) 0.76976(13) 0.08036(12) 0.0605(5) Uani 1 1 d . . . C7 C 0.7354(2) 0.66012(16) 0.27980(15) 0.0803(7) Uani 1 1 d . . . H7A H 0.8161 0.6458 0.2978 0.120 Uiso 1 1 calc R . . H7B H 0.6918 0.6086 0.2619 0.120 Uiso 1 1 calc R . . H7C H 0.7083 0.6857 0.3250 0.120 Uiso 1 1 calc R . . C8 C 0.5590(2) 0.93298(15) 0.13796(17) 0.0800(6) Uani 1 1 d . . . H8A H 0.5942 0.9806 0.1155 0.120 Uiso 1 1 calc R . . H8B H 0.5528 0.9465 0.1936 0.120 Uiso 1 1 calc R . . H8C H 0.4830 0.9226 0.1042 0.120 Uiso 1 1 calc R . . C9 C 0.8362(2) 0.75585(18) 0.01323(16) 0.0846(7) Uani 1 1 d . . . H9A H 0.9134 0.7366 0.0379 0.127 Uiso 1 1 calc R . . H9B H 0.8400 0.8092 -0.0158 0.127 Uiso 1 1 calc R . . H9C H 0.7977 0.7129 -0.0250 0.127 Uiso 1 1 calc R . . C11 C 1.14812(19) 0.74732(18) 0.26631(16) 0.0802(6) Uani 1 1 d . . . C12 C 1.03222(18) 0.73439(15) 0.22892(14) 0.0700(6) Uani 1 1 d . . . H12 H 0.9797 0.7796 0.2267 0.084 Uiso 1 1 calc R . . C13 C 0.99386(17) 0.65507(13) 0.19487(12) 0.0623(5) Uani 1 1 d . . . C14 C 1.0741(2) 0.58895(16) 0.19850(15) 0.0787(6) Uani 1 1 d . . . H14 H 1.0500 0.5351 0.1760 0.094 Uiso 1 1 calc R . . C15 C 1.1893(2) 0.6025(2) 0.23524(17) 0.0930(8) Uani 1 1 d . . . H15 H 1.2426 0.5579 0.2367 0.112 Uiso 1 1 calc R . . C16 C 1.2262(2) 0.6812(2) 0.26960(18) 0.0942(8) Uani 1 1 d . . . H16 H 1.3039 0.6896 0.2950 0.113 Uiso 1 1 calc R . . C17 C 0.86771(18) 0.63766(14) 0.15261(15) 0.0716(6) Uani 1 1 d . . . H17A H 0.8655 0.6177 0.0966 0.086 Uiso 1 1 calc R . . H17B H 0.8396 0.5908 0.1819 0.086 Uiso 1 1 calc R . . C21 C 0.7582(2) 0.94694(13) 0.42304(14) 0.0740(6) Uani 1 1 d . . . C22 C 0.71743(18) 0.89757(12) 0.35198(13) 0.0642(5) Uani 1 1 d . . . H22 H 0.7599 0.8947 0.3109 0.077 Uiso 1 1 calc R . . C23 C 0.61389(18) 0.85288(13) 0.34251(12) 0.0646(5) Uani 1 1 d . . . C24 C 0.5525(2) 0.85780(17) 0.40492(15) 0.0858(7) Uani 1 1 d . . . H24 H 0.4831 0.8278 0.3996 0.103 Uiso 1 1 calc R . . C25 C 0.5939(3) 0.9070(2) 0.47491(17) 0.1004(9) Uani 1 1 d . . . H25 H 0.5518 0.9098 0.5162 0.121 Uiso 1 1 calc R . . C26 C 0.6960(3) 0.95177(17) 0.48448(15) 0.0941(9) Uani 1 1 d . . . H26 H 0.7231 0.9850 0.5318 0.113 Uiso 1 1 calc R . . C27 C 0.56572(18) 0.80016(15) 0.26540(14) 0.0709(6) Uani 1 1 d . . . H27A H 0.5493 0.7424 0.2827 0.085 Uiso 1 1 calc R . . H27B H 0.4924 0.8256 0.2375 0.085 Uiso 1 1 calc R . . C31 C 0.9195(2) 1.06049(16) 0.0805(2) 0.0944(9) Uani 1 1 d . . . C32 C 0.84024(19) 0.99389(14) 0.07912(17) 0.0751(6) Uani 1 1 d . . . H32 H 0.8387 0.9639 0.1277 0.090 Uiso 1 1 calc R . . C33 C 0.7639(2) 0.97207(14) 0.00620(16) 0.0735(6) Uani 1 1 d . . . C34 C 0.7673(3) 1.01606(17) -0.0666(2) 0.0944(8) Uani 1 1 d . . . H34 H 0.7169 1.0016 -0.1164 0.113 Uiso 1 1 calc R . . C35 C 0.8478(4) 1.0822(2) -0.0633(3) 0.1256(14) Uani 1 1 d . . . H35 H 0.8516 1.1114 -0.1119 0.151 Uiso 1 1 calc R . . C36 C 0.9210(3) 1.1055(2) 0.0090(4) 0.1205(13) Uani 1 1 d . . . H36 H 0.9719 1.1515 0.0100 0.145 Uiso 1 1 calc R . . C37 C 0.6752(2) 0.90025(15) 0.00201(14) 0.0757(6) Uani 1 1 d . . . H37A H 0.5991 0.9264 -0.0048 0.091 Uiso 1 1 calc R . . H37B H 0.6749 0.8660 -0.0473 0.091 Uiso 1 1 calc R . . Ga1 Ga 1.00849(7) 0.96827(5) 0.30697(6) 0.1111(5) Uani 0.4393(18) 1 d P A 1 N1 N 1.0283(14) 1.1399(11) 0.4254(13) 0.092(4) Uani 0.4393(18) 1 d P A 1 C51 C 1.1131(9) 1.1741(6) 0.3911(6) 0.086(2) Uani 0.4393(18) 1 d P A 1 H51 H 1.1333 1.1483 0.3454 0.103 Uiso 0.4393(18) 1 calc PR A 1 C52 C 1.1655(16) 1.2446(14) 0.4246(12) 0.079(3) Uani 0.4393(18) 1 d P A 1 H52 H 1.2225 1.2695 0.4012 0.095 Uiso 0.4393(18) 1 calc PR A 1 C53 C 1.138(2) 1.2833(8) 0.494(2) 0.078(5) Uani 0.4393(18) 1 d P A 1 H53 H 1.1736 1.3344 0.5164 0.093 Uiso 0.4393(18) 1 calc PR A 1 C54 C 1.0545(18) 1.2410(11) 0.5291(12) 0.091(4) Uani 0.4393(18) 1 d P A 1 H54 H 1.0370 1.2603 0.5783 0.109 Uiso 0.4393(18) 1 calc PR A 1 C55 C 0.9961(16) 1.1653(10) 0.4846(10) 0.060(3) Uani 0.4393(18) 1 d P A 1 H55 H 0.9356 1.1380 0.5023 0.072 Uiso 0.4393(18) 1 calc PR A 1 N1A N 0.9844(5) 1.1942(5) 0.5288(5) 0.1025(17) Uani 0.5607(18) 1 d P A 2 C51A C 1.0571(16) 1.2645(10) 0.5548(9) 0.097(3) Uani 0.5607(18) 1 d P A 2 H51A H 1.0503 1.2985 0.6000 0.116 Uiso 0.5607(18) 1 calc PR A 2 C52A C 1.1359(16) 1.2797(10) 0.5114(17) 0.094(6) Uani 0.5607(18) 1 d P A 2 H52A H 1.1909 1.3226 0.5292 0.113 Uiso 0.5607(18) 1 calc PR A 2 C53A C 1.1393(13) 1.2370(13) 0.4451(10) 0.092(3) Uani 0.5607(18) 1 d P A 2 H53A H 1.1933 1.2526 0.4144 0.110 Uiso 0.5607(18) 1 calc PR A 2 C54A C 1.0615(10) 1.1653(8) 0.4166(9) 0.083(3) Uani 0.5607(18) 1 d P A 2 H54A H 1.0650 1.1344 0.3689 0.099 Uiso 0.5607(18) 1 calc PR A 2 C55A C 0.9858(16) 1.1462(9) 0.4616(10) 0.074(3) Uani 0.5607(18) 1 d P A 2 H55A H 0.9343 1.1004 0.4470 0.088 Uiso 0.5607(18) 1 calc PR A 2 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 0.0755(11) 0.1109(14) 0.1365(17) -0.0235(12) -0.0105(11) -0.0163(10) O2 0.1039(13) 0.0635(9) 0.0968(12) -0.0113(8) -0.0195(10) -0.0066(9) O3 0.0731(11) 0.0909(13) 0.201(2) -0.0522(15) 0.0465(13) -0.0278(9) C1 0.0548(10) 0.0528(10) 0.0699(12) -0.0112(9) 0.0144(9) -0.0132(8) C2 0.0537(10) 0.0581(11) 0.0638(11) -0.0077(9) 0.0108(9) -0.0143(8) C3 0.0505(10) 0.0631(11) 0.0636(11) -0.0134(9) 0.0120(8) -0.0134(8) C4 0.0533(10) 0.0586(11) 0.0665(12) -0.0102(9) 0.0086(9) -0.0085(8) C5 0.0578(10) 0.0587(11) 0.0631(11) -0.0069(9) 0.0085(9) -0.0133(9) C6 0.0564(10) 0.0625(11) 0.0639(12) -0.0124(9) 0.0161(9) -0.0135(9) C7 0.0853(15) 0.0760(15) 0.0799(15) 0.0081(12) 0.0186(12) -0.0131(12) C8 0.0699(13) 0.0725(14) 0.0932(16) -0.0111(12) 0.0085(12) 0.0067(11) C9 0.0867(15) 0.0906(16) 0.0855(16) -0.0122(13) 0.0384(13) -0.0113(13) C11 0.0624(13) 0.0921(17) 0.0815(15) -0.0014(13) 0.0059(11) -0.0006(12) C12 0.0609(12) 0.0692(13) 0.0792(14) -0.0029(11) 0.0139(10) 0.0005(10) C13 0.0649(11) 0.0615(11) 0.0630(11) 0.0042(9) 0.0197(9) 0.0035(9) C14 0.0935(16) 0.0732(14) 0.0741(14) 0.0056(11) 0.0284(12) 0.0180(12) C15 0.0825(16) 0.106(2) 0.0886(17) 0.0087(15) 0.0156(13) 0.0315(15) C16 0.0661(14) 0.123(2) 0.0884(17) 0.0042(16) 0.0061(12) 0.0179(15) C17 0.0701(12) 0.0559(12) 0.0905(15) -0.0111(11) 0.0214(11) -0.0038(9) C21 0.0939(16) 0.0493(11) 0.0682(14) 0.0023(10) -0.0052(12) 0.0096(11) C22 0.0712(12) 0.0552(11) 0.0631(12) -0.0039(9) 0.0079(9) 0.0031(9) C23 0.0720(12) 0.0612(12) 0.0623(12) -0.0002(9) 0.0183(9) 0.0037(10) C24 0.1057(18) 0.0864(16) 0.0728(15) -0.0013(13) 0.0360(13) -0.0006(14) C25 0.145(3) 0.0942(19) 0.0713(16) 0.0001(14) 0.0442(16) 0.0098(19) C26 0.152(3) 0.0690(15) 0.0561(13) -0.0030(11) 0.0114(15) 0.0163(17) C27 0.0619(12) 0.0783(14) 0.0768(14) -0.0121(11) 0.0243(10) -0.0111(10) C31 0.0759(15) 0.0629(14) 0.161(3) -0.0165(17) 0.0625(18) -0.0056(12) C32 0.0694(13) 0.0611(12) 0.1029(18) -0.0101(12) 0.0367(13) -0.0085(10) C33 0.0817(14) 0.0594(12) 0.0900(16) 0.0029(11) 0.0422(13) 0.0047(10) C34 0.110(2) 0.0813(16) 0.109(2) 0.0157(15) 0.0608(17) 0.0157(14) C35 0.142(3) 0.086(2) 0.183(4) 0.037(2) 0.110(3) 0.015(2) C36 0.106(2) 0.0717(18) 0.212(4) 0.007(2) 0.095(3) -0.0069(16) C37 0.0842(14) 0.0721(14) 0.0688(13) 0.0010(11) 0.0127(11) -0.0087(11) Ga1 0.0963(6) 0.0973(6) 0.1351(8) -0.0385(5) 0.0151(5) -0.0093(4) N1 0.089(9) 0.076(8) 0.098(7) 0.030(7) -0.010(6) -0.011(5) C51 0.100(6) 0.063(4) 0.089(6) 0.004(4) 0.008(4) -0.002(4) C52 0.094(8) 0.070(6) 0.071(8) 0.014(5) 0.011(5) -0.010(5) C53 0.104(8) 0.036(5) 0.079(11) 0.003(5) -0.011(6) -0.008(4) C54 0.083(7) 0.071(9) 0.110(11) -0.005(5) 0.002(7) -0.007(7) C55 0.067(5) 0.040(7) 0.065(9) -0.017(5) -0.002(6) -0.010(4) N1A 0.083(4) 0.085(4) 0.118(5) 0.018(4) -0.024(3) 0.002(3) C51A 0.089(5) 0.078(8) 0.104(8) -0.008(4) -0.018(6) 0.001(5) C52A 0.081(6) 0.104(9) 0.082(10) 0.012(4) -0.014(5) -0.021(5) C53A 0.098(7) 0.090(6) 0.085(9) 0.025(6) 0.015(5) -0.011(5) C54A 0.086(8) 0.085(8) 0.075(5) 0.001(6) 0.013(5) 0.011(6) C55A 0.081(6) 0.049(6) 0.078(9) -0.016(5) -0.011(5) -0.004(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C11 1.376(3) . ? O2 C21 1.380(3) . ? O3 C31 1.371(4) . ? C1 C6 1.400(3) . ? C1 C2 1.403(3) . ? C1 C17 1.509(3) . ? C2 C3 1.401(3) . ? C2 C7 1.506(3) . ? C3 C4 1.404(3) . ? C3 C27 1.511(3) . ? C4 C5 1.401(3) . ? C4 C8 1.509(3) . ? C5 C6 1.401(3) . ? C5 C37 1.516(3) . ? C6 C9 1.510(3) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C11 C16 1.371(4) . ? C11 C12 1.387(3) . ? C12 C13 1.384(3) . ? C12 H12 0.9300 . ? C13 C14 1.387(3) . ? C13 C17 1.524(3) . ? C14 C15 1.379(4) . ? C14 H14 0.9300 . ? C15 C16 1.372(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C21 C26 1.379(4) . ? C21 C22 1.394(3) . ? C22 C23 1.384(3) . ? C22 H22 0.9300 . ? C23 C24 1.386(3) . ? C23 C27 1.513(3) . ? C24 C25 1.380(4) . ? C24 H24 0.9300 . ? C25 C26 1.370(4) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C31 C36 1.374(5) . ? C31 C32 1.389(3) . ? C32 C33 1.378(4) . ? C32 H32 0.9300 . ? C33 C34 1.389(4) . ? C33 C37 1.518(3) . ? C34 C35 1.389(5) . ? C34 H34 0.9300 . ? C35 C36 1.359(6) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? N1 C55 1.19(3) . ? N1 C51 1.361(15) . ? C51 C52 1.31(3) . ? C51 H51 0.9300 . ? C52 C53 1.39(4) . ? C52 H52 0.9300 . ? C53 C54 1.41(4) . ? C53 H53 0.9300 . ? C54 C55 1.472(15) . ? C54 H54 0.9300 . ? C55 H55 0.9300 . ? N1A C55A 1.338(11) . ? N1A C51A 1.393(16) . ? C51A C52A 1.32(3) . ? C51A H51A 0.9300 . ? C52A C53A 1.29(3) . ? C52A H52A 0.9300 . ? C53A C54A 1.45(2) . ? C53A H53A 0.9300 . ? C54A C55A 1.32(3) . ? C54A H54A 0.9300 . ? C55A H55A 0.9300 . ? 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 C6 C1 C2 120.16(18) . . ? C6 C1 C17 119.74(18) . . ? C2 C1 C17 120.08(19) . . ? C3 C2 C1 119.82(18) . . ? C3 C2 C7 120.71(19) . . ? C1 C2 C7 119.47(19) . . ? C2 C3 C4 120.02(17) . . ? C2 C3 C27 119.93(19) . . ? C4 C3 C27 120.05(19) . . ? C5 C4 C3 119.64(18) . . ? C5 C4 C8 120.01(19) . . ? C3 C4 C8 120.35(19) . . ? C6 C5 C4 120.24(19) . . ? C6 C5 C37 119.57(19) . . ? C4 C5 C37 120.18(19) . . ? C1 C6 C5 119.83(18) . . ? C1 C6 C9 119.77(19) . . ? C5 C6 C9 120.4(2) . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C16 C11 O1 117.8(2) . . ? C16 C11 C12 120.0(3) . . ? O1 C11 C12 122.2(2) . . ? C13 C12 C11 120.8(2) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C14 118.5(2) . . ? C12 C13 C17 122.86(18) . . ? C14 C13 C17 118.7(2) . . ? C15 C14 C13 120.4(2) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C16 C15 C14 120.6(2) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C11 C16 C15 119.7(2) . . ? C11 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C1 C17 C13 116.75(17) . . ? C1 C17 H17A 108.1 . . ? C13 C17 H17A 108.1 . . ? C1 C17 H17B 108.1 . . ? C13 C17 H17B 108.1 . . ? H17A C17 H17B 107.3 . . ? C26 C21 O2 119.7(2) . . ? C26 C21 C22 120.5(2) . . ? O2 C21 C22 119.8(2) . . ? C23 C22 C21 120.1(2) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C22 C23 C24 118.8(2) . . ? C22 C23 C27 121.58(18) . . ? C24 C23 C27 119.6(2) . . ? C25 C24 C23 120.4(3) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C26 C25 C24 121.1(3) . . ? C26 C25 H25 119.5 . . ? C24 C25 H25 119.5 . . ? C25 C26 C21 119.1(2) . . ? C25 C26 H26 120.5 . . ? C21 C26 H26 120.5 . . ? C3 C27 C23 116.54(16) . . ? C3 C27 H27A 108.2 . . ? C23 C27 H27A 108.2 . . ? C3 C27 H27B 108.2 . . ? C23 C27 H27B 108.2 . . ? H27A C27 H27B 107.3 . . ? O3 C31 C36 118.1(3) . . ? O3 C31 C32 122.1(3) . . ? C36 C31 C32 119.8(3) . . ? C33 C32 C31 120.4(3) . . ? C33 C32 H32 119.8 . . ? C31 C32 H32 119.8 . . ? C32 C33 C34 119.8(2) . . ? C32 C33 C37 122.1(2) . . ? C34 C33 C37 118.1(3) . . ? C33 C34 C35 118.5(4) . . ? C33 C34 H34 120.8 . . ? C35 C34 H34 120.8 . . ? C36 C35 C34 121.8(3) . . ? C36 C35 H35 119.1 . . ? C34 C35 H35 119.1 . . ? C35 C36 C31 119.6(3) . . ? C35 C36 H36 120.2 . . ? C31 C36 H36 120.2 . . ? C5 C37 C33 116.15(19) . . ? C5 C37 H37A 108.2 . . ? C33 C37 H37A 108.2 . . ? C5 C37 H37B 108.2 . . ? C33 C37 H37B 108.2 . . ? H37A C37 H37B 107.4 . . ? C55 N1 C51 127.6(16) . . ? C52 C51 N1 118.0(14) . . ? C52 C51 H51 121.0 . . ? N1 C51 H51 121.0 . . ? C51 C52 C53 122.0(13) . . ? C51 C52 H52 119.0 . . ? C53 C52 H52 119.0 . . ? C54 C53 C52 116.6(16) . . ? C54 C53 H53 121.7 . . ? C52 C53 H53 121.7 . . ? C53 C54 C55 117.3(18) . . ? C53 C54 H54 121.3 . . ? C55 C54 H54 121.3 . . ? N1 C55 C54 118.2(15) . . ? N1 C55 H55 120.9 . . ? C54 C55 H55 120.9 . . ? C55A N1A C51A 124.7(12) . . ? C52A C51A N1A 115.7(12) . . ? C52A C51A H51A 122.2 . . ? N1A C51A H51A 122.2 . . ? C53A C52A C51A 122.0(16) . . ? C53A C52A H52A 119.0 . . ? C51A C52A H52A 119.0 . . ? C52A C53A C54A 122.2(13) . . ? C52A C53A H53A 118.9 . . ? C54A C53A H53A 118.9 . . ? C55A C54A C53A 116.7(11) . . ? C55A C54A H54A 121.6 . . ? C53A C54A H54A 121.6 . . ? C54A C55A N1A 118.5(12) . . ? C54A C55A H55A 120.8 . . ? N1A C55A H55A 120.8 . . ? 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 C6 C1 C2 C3 -0.8(3) . . . . ? C17 C1 C2 C3 -179.20(16) . . . . ? C6 C1 C2 C7 178.96(17) . . . . ? C17 C1 C2 C7 0.5(3) . . . . ? C1 C2 C3 C4 -3.7(3) . . . . ? C7 C2 C3 C4 176.58(17) . . . . ? C1 C2 C3 C27 175.47(17) . . . . ? C7 C2 C3 C27 -4.2(3) . . . . ? C2 C3 C4 C5 6.5(3) . . . . ? C27 C3 C4 C5 -172.63(17) . . . . ? C2 C3 C4 C8 -172.99(17) . . . . ? C27 C3 C4 C8 7.8(3) . . . . ? C3 C4 C5 C6 -4.9(3) . . . . ? C8 C4 C5 C6 174.58(17) . . . . ? C3 C4 C5 C37 173.90(17) . . . . ? C8 C4 C5 C37 -6.6(3) . . . . ? C2 C1 C6 C5 2.4(3) . . . . ? C17 C1 C6 C5 -179.20(17) . . . . ? C2 C1 C6 C9 -177.89(18) . . . . ? C17 C1 C6 C9 0.5(3) . . . . ? C4 C5 C6 C1 0.5(3) . . . . ? C37 C5 C6 C1 -178.34(17) . . . . ? C4 C5 C6 C9 -179.24(18) . . . . ? C37 C5 C6 C9 1.9(3) . . . . ? C16 C11 C12 C13 0.2(4) . . . . ? O1 C11 C12 C13 -179.6(2) . . . . ? C11 C12 C13 C14 -0.4(3) . . . . ? C11 C12 C13 C17 -179.6(2) . . . . ? C12 C13 C14 C15 -0.1(3) . . . . ? C17 C13 C14 C15 179.1(2) . . . . ? C13 C14 C15 C16 0.8(4) . . . . ? O1 C11 C16 C15 -179.7(3) . . . . ? C12 C11 C16 C15 0.5(4) . . . . ? C14 C15 C16 C11 -1.0(4) . . . . ? C6 C1 C17 C13 87.5(2) . . . . ? C2 C1 C17 C13 -94.0(2) . . . . ? C12 C13 C17 C1 1.3(3) . . . . ? C14 C13 C17 C1 -177.90(19) . . . . ? C26 C21 C22 C23 0.0(3) . . . . ? O2 C21 C22 C23 -179.38(19) . . . . ? C21 C22 C23 C24 -0.4(3) . . . . ? C21 C22 C23 C27 178.69(19) . . . . ? C22 C23 C24 C25 0.5(4) . . . . ? C27 C23 C24 C25 -178.7(2) . . . . ? C23 C24 C25 C26 -0.1(4) . . . . ? C24 C25 C26 C21 -0.3(4) . . . . ? O2 C21 C26 C25 179.7(2) . . . . ? C22 C21 C26 C25 0.3(4) . . . . ? C2 C3 C27 C23 90.8(2) . . . . ? C4 C3 C27 C23 -90.1(2) . . . . ? C22 C23 C27 C3 5.5(3) . . . . ? C24 C23 C27 C3 -175.4(2) . . . . ? O3 C31 C32 C33 -179.5(2) . . . . ? C36 C31 C32 C33 0.7(3) . . . . ? C31 C32 C33 C34 0.9(3) . . . . ? C31 C32 C33 C37 -179.5(2) . . . . ? C32 C33 C34 C35 -0.8(4) . . . . ? C37 C33 C34 C35 179.7(2) . . . . ? C33 C34 C35 C36 -1.1(4) . . . . ? C34 C35 C36 C31 2.7(5) . . . . ? O3 C31 C36 C35 177.7(3) . . . . ? C32 C31 C36 C35 -2.5(4) . . . . ? C6 C5 C37 C33 -83.9(2) . . . . ? C4 C5 C37 C33 97.2(2) . . . . ? C32 C33 C37 C5 -14.3(3) . . . . ? C34 C33 C37 C5 165.3(2) . . . . ? C55 N1 C51 C52 -2(3) . . . . ? N1 C51 C52 C53 1(3) . . . . ? C51 C52 C53 C54 2(3) . . . . ? C52 C53 C54 C55 -6(3) . . . . ? C51 N1 C55 C54 -2(3) . . . . ? C53 C54 C55 N1 5(3) . . . . ? C55A N1A C51A C52A -4(2) . . . . ? N1A C51A C52A C53A 6(3) . . . . ? C51A C52A C53A C54A -4(3) . . . . ? C52A C53A C54A C55A 1(2) . . . . ? C53A C54A C55A N1A 1(2) . . . . ? C51A N1A C55A C54A 1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.420 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.062