# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Deepak B. Salunke' _publ_contact_author_email deepsalunke@yahoo.com loop_ _publ_author_name P.-T.Lin D.B.Salunke L.-H.Chen C.-M.Sun # Attachment 'CM-Sun-4k.cif' data_4k _database_code_depnum_ccdc_archive 'CCDC 782682' #TrackingRef 'CM-Sun-4k.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Methyl 6-(3-nitrophenyl)-1,2,6,7-tetrahydroindolo[1,7-ab][1,5]benzodiazepine-9-carboxylate' ; _chemical_name_common ; 'Methyl 6-(3-nitrophenyl)-1,2,6,7-tetrahydroindolo(1,7- ab)(1,5)benzodiazepine-9- ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H19 N3 O4' _chemical_formula_weight 401.41 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.7967(2) _cell_length_b 12.1325(3) _cell_length_c 12.4682(3) _cell_angle_alpha 69.5460(10) _cell_angle_beta 81.7740(10) _cell_angle_gamma 85.6650(10) _cell_volume 953.04(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5916 _cell_measurement_theta_min 2.9093 _cell_measurement_theta_max 26.3934 _exptl_crystal_description Lump _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7211 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 15954 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_av_sigmaI/netI 0.0186 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 26.43 _reflns_number_total 3916 _reflns_number_gt 3226 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.34A (Bruker AXS, 2006)' _computing_data_reduction 'SAINT V7.34A (Bruker AXS, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _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^)+(0.0996P)^2^+0.2065P] 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 3916 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0547 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1587 _refine_ls_wR_factor_gt 0.1376 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.000 _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 C1 C 0.2217(2) 0.68765(14) 0.23577(13) 0.0335(4) Uani 1 1 d . . . H1 H 0.0861 0.7256 0.2381 0.040 Uiso 1 1 calc R . . C2 C 0.1895(2) 0.55826(14) 0.26813(13) 0.0337(4) Uani 1 1 d . . . C3 C 0.0167(3) 0.51070(17) 0.33930(16) 0.0444(4) Uani 1 1 d . . . H3 H -0.0731 0.5606 0.3683 0.053 Uiso 1 1 calc R . . C4 C -0.0290(3) 0.39385(18) 0.36926(17) 0.0515(5) Uani 1 1 d . . . H4 H -0.1478 0.3645 0.4183 0.062 Uiso 1 1 calc R . . C5 C 0.0988(3) 0.31992(17) 0.32764(16) 0.0473(4) Uani 1 1 d . . . H5 H 0.0673 0.2399 0.3463 0.057 Uiso 1 1 calc R . . C6 C 0.2728(3) 0.36356(14) 0.25872(14) 0.0373(4) Uani 1 1 d . . . C7 C 0.4332(3) 0.30171(16) 0.20433(15) 0.0446(4) Uani 1 1 d . . . H7A H 0.3854 0.2802 0.1431 0.053 Uiso 1 1 calc R . . H7B H 0.4814 0.2296 0.2625 0.053 Uiso 1 1 calc R . . C8 C 0.5965(3) 0.39181(15) 0.15392(16) 0.0422(4) Uani 1 1 d . . . H8A H 0.7103 0.3685 0.1995 0.051 Uiso 1 1 calc R . . H8B H 0.6445 0.3990 0.0730 0.051 Uiso 1 1 calc R . . C9 C 0.6097(2) 0.60734(14) 0.10899(13) 0.0319(3) Uani 1 1 d . . . C10 C 0.8127(2) 0.59996(15) 0.07012(15) 0.0393(4) Uani 1 1 d . . . H10 H 0.8771 0.5246 0.0869 0.047 Uiso 1 1 calc R . . C11 C 0.9219(2) 0.69861(16) 0.00830(15) 0.0401(4) Uani 1 1 d . . . H11 H 1.0584 0.6903 -0.0183 0.048 Uiso 1 1 calc R . . C12 C 0.8330(2) 0.81008(15) -0.01516(13) 0.0356(4) Uani 1 1 d . . . C13 C 0.6347(2) 0.81908(14) 0.02778(13) 0.0342(4) Uani 1 1 d . . . H13 H 0.5750 0.8952 0.0152 0.041 Uiso 1 1 calc R . . C14 C 0.5203(2) 0.72161(14) 0.08825(12) 0.0308(3) Uani 1 1 d . . . C15 C 0.3191(2) 0.48221(14) 0.22862(12) 0.0326(3) Uani 1 1 d . . . C16 C 0.3264(2) 0.71785(14) 0.32169(13) 0.0335(4) Uani 1 1 d . . . C17 C 0.4826(3) 0.64961(16) 0.37479(15) 0.0429(4) Uani 1 1 d . . . H17 H 0.5271 0.5808 0.3576 0.051 Uiso 1 1 calc R . . C18 C 0.5744(3) 0.68020(19) 0.45238(16) 0.0494(5) Uani 1 1 d . . . H18 H 0.6821 0.6329 0.4868 0.059 Uiso 1 1 calc R . . C19 C 0.5109(3) 0.77876(17) 0.48008(15) 0.0459(4) Uani 1 1 d . . . H19 H 0.5720 0.8000 0.5338 0.055 Uiso 1 1 calc R . . C20 C 0.3562(3) 0.84512(15) 0.42733(15) 0.0425(4) Uani 1 1 d . . . C21 C 0.2645(3) 0.81802(14) 0.34813(14) 0.0388(4) Uani 1 1 d . . . H21 H 0.1601 0.8674 0.3121 0.047 Uiso 1 1 calc R . . C22 C 0.9400(3) 0.91895(15) -0.08487(14) 0.0378(4) Uani 1 1 d . . . C23 C 1.2409(3) 0.99701(19) -0.19618(18) 0.0558(5) Uani 1 1 d . . . H23A H 1.1914 1.0313 -0.2713 0.084 Uiso 1 1 calc R . . H23B H 1.3807 0.9722 -0.2073 0.084 Uiso 1 1 calc R . . H23C H 1.2295 1.0559 -0.1580 0.084 Uiso 1 1 calc R . . N1 N 0.31603(19) 0.73889(12) 0.11619(11) 0.0345(3) Uani 1 1 d . . . H1A H 0.2438 0.7807 0.0618 0.041 Uiso 1 1 calc R . . N2 N 0.5042(2) 0.50438(11) 0.15980(12) 0.0359(3) Uani 1 1 d . . . N3 N 0.2809(3) 0.94756(17) 0.45863(18) 0.0638(5) Uani 1 1 d . . . O1 O 0.3048(3) 0.94876(18) 0.55306(18) 0.0905(6) Uani 1 1 d . . . O2 O 0.2003(4) 1.02668(17) 0.3886(2) 0.1125(9) Uani 1 1 d . . . O3 O 0.8687(2) 1.01712(11) -0.10340(12) 0.0506(3) Uani 1 1 d . . . O4 O 1.12547(19) 0.89683(11) -0.12566(12) 0.0497(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 0.0310(8) 0.0362(8) 0.0348(8) -0.0156(7) -0.0041(6) 0.0053(6) C2 0.0343(8) 0.0357(8) 0.0335(8) -0.0141(6) -0.0065(6) 0.0010(6) C3 0.0380(9) 0.0479(10) 0.0458(9) -0.0169(8) 0.0007(7) 0.0000(7) C4 0.0438(10) 0.0500(11) 0.0535(11) -0.0109(9) 0.0039(8) -0.0092(8) C5 0.0516(11) 0.0383(9) 0.0499(10) -0.0109(8) -0.0058(8) -0.0101(8) C6 0.0467(9) 0.0335(8) 0.0340(8) -0.0124(7) -0.0093(7) -0.0019(7) C7 0.0615(11) 0.0344(9) 0.0410(9) -0.0177(7) -0.0032(8) -0.0026(8) C8 0.0470(10) 0.0335(9) 0.0489(9) -0.0196(7) -0.0047(8) 0.0066(7) C9 0.0340(8) 0.0328(8) 0.0308(7) -0.0137(6) -0.0050(6) 0.0025(6) C10 0.0367(9) 0.0332(8) 0.0478(9) -0.0155(7) -0.0042(7) 0.0063(7) C11 0.0326(8) 0.0415(9) 0.0474(9) -0.0183(8) -0.0021(7) 0.0017(7) C12 0.0372(8) 0.0371(9) 0.0350(8) -0.0153(7) -0.0055(6) -0.0001(7) C13 0.0397(8) 0.0313(8) 0.0345(8) -0.0149(6) -0.0079(6) 0.0051(6) C14 0.0330(8) 0.0340(8) 0.0282(7) -0.0142(6) -0.0065(6) 0.0038(6) C15 0.0362(8) 0.0349(8) 0.0285(7) -0.0123(6) -0.0066(6) -0.0011(6) C16 0.0360(8) 0.0329(8) 0.0312(7) -0.0124(6) 0.0003(6) 0.0004(6) C17 0.0439(9) 0.0458(10) 0.0446(9) -0.0234(8) -0.0096(7) 0.0114(8) C18 0.0473(10) 0.0596(12) 0.0472(10) -0.0249(9) -0.0139(8) 0.0093(9) C19 0.0510(10) 0.0524(11) 0.0406(9) -0.0223(8) -0.0064(8) -0.0070(8) C20 0.0549(10) 0.0326(9) 0.0420(9) -0.0168(7) 0.0004(8) -0.0063(8) C21 0.0463(9) 0.0302(8) 0.0386(8) -0.0111(7) -0.0050(7) 0.0032(7) C22 0.0424(9) 0.0380(9) 0.0344(8) -0.0136(7) -0.0066(7) -0.0016(7) C23 0.0562(12) 0.0528(12) 0.0539(11) -0.0161(9) 0.0095(9) -0.0157(9) N1 0.0325(7) 0.0377(7) 0.0318(6) -0.0105(6) -0.0076(5) 0.0077(5) N2 0.0389(7) 0.0297(7) 0.0402(7) -0.0162(6) -0.0003(6) 0.0029(6) N3 0.0802(13) 0.0467(10) 0.0772(12) -0.0375(10) -0.0093(10) -0.0003(9) O1 0.1076(15) 0.1016(15) 0.0972(14) -0.0786(13) -0.0146(11) 0.0068(12) O2 0.178(2) 0.0532(11) 0.1256(18) -0.0494(12) -0.0566(17) 0.0423(13) O3 0.0558(8) 0.0350(7) 0.0553(8) -0.0102(6) -0.0038(6) 0.0005(6) O4 0.0454(7) 0.0434(7) 0.0544(8) -0.0135(6) 0.0066(6) -0.0062(6) _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 C1 N1 1.470(2) . ? C1 C2 1.503(2) . ? C1 C16 1.523(2) . ? C1 H1 1.0000 . ? C2 C15 1.393(2) . ? C2 C3 1.395(2) . ? C3 C4 1.382(3) . ? C3 H3 0.9500 . ? C4 C5 1.381(3) . ? C4 H4 0.9500 . ? C5 C6 1.379(3) . ? C5 H5 0.9500 . ? C6 C15 1.403(2) . ? C6 C7 1.494(2) . ? C7 C8 1.525(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 N2 1.481(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N2 1.389(2) . ? C9 C10 1.402(2) . ? C9 C14 1.423(2) . ? C10 C11 1.380(2) . ? C10 H10 0.9500 . ? C11 C12 1.389(2) . ? C11 H11 0.9500 . ? C12 C13 1.388(2) . ? C12 C22 1.480(2) . ? C13 C14 1.386(2) . ? C13 H13 0.9500 . ? C14 N1 1.400(2) . ? C15 N2 1.404(2) . ? C16 C21 1.388(2) . ? C16 C17 1.391(2) . ? C17 C18 1.387(2) . ? C17 H17 0.9500 . ? C18 C19 1.380(3) . ? C18 H18 0.9500 . ? C19 C20 1.374(3) . ? C19 H19 0.9500 . ? C20 C21 1.380(2) . ? C20 N3 1.464(2) . ? C21 H21 0.9500 . ? C22 O3 1.208(2) . ? C22 O4 1.334(2) . ? C23 O4 1.437(2) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? N1 H1A 0.8800 . ? N3 O2 1.207(3) . ? N3 O1 1.216(3) . ? 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 C2 111.64(12) . . ? N1 C1 C16 112.97(13) . . ? C2 C1 C16 113.63(13) . . ? N1 C1 H1 106.0 . . ? C2 C1 H1 106.0 . . ? C16 C1 H1 106.0 . . ? C15 C2 C3 117.20(16) . . ? C15 C2 C1 124.10(14) . . ? C3 C2 C1 118.67(15) . . ? C4 C3 C2 122.51(18) . . ? C4 C3 H3 118.7 . . ? C2 C3 H3 118.7 . . ? C5 C4 C3 119.72(17) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C6 C5 C4 119.27(17) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C5 C6 C15 120.91(16) . . ? C5 C6 C7 129.20(16) . . ? C15 C6 C7 109.88(15) . . ? C6 C7 C8 103.81(14) . . ? C6 C7 H7A 111.0 . . ? C8 C7 H7A 111.0 . . ? C6 C7 H7B 111.0 . . ? C8 C7 H7B 111.0 . . ? H7A C7 H7B 109.0 . . ? N2 C8 C7 105.64(14) . . ? N2 C8 H8A 110.6 . . ? C7 C8 H8A 110.6 . . ? N2 C8 H8B 110.6 . . ? C7 C8 H8B 110.6 . . ? H8A C8 H8B 108.7 . . ? N2 C9 C10 118.98(14) . . ? N2 C9 C14 123.34(14) . . ? C10 C9 C14 117.59(14) . . ? C11 C10 C9 122.10(15) . . ? C11 C10 H10 119.0 . . ? C9 C10 H10 119.0 . . ? C10 C11 C12 120.26(15) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 118.31(15) . . ? C13 C12 C22 118.89(15) . . ? C11 C12 C22 122.80(15) . . ? C14 C13 C12 122.72(15) . . ? C14 C13 H13 118.6 . . ? C12 C13 H13 118.6 . . ? C13 C14 N1 118.61(14) . . ? C13 C14 C9 118.91(14) . . ? N1 C14 C9 122.14(14) . . ? C2 C15 C6 120.36(15) . . ? C2 C15 N2 129.59(14) . . ? C6 C15 N2 110.05(14) . . ? C21 C16 C17 118.28(15) . . ? C21 C16 C1 118.82(14) . . ? C17 C16 C1 122.90(14) . . ? C18 C17 C16 121.18(17) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C19 C18 C17 120.56(17) . . ? C19 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C20 C19 C18 117.65(16) . . ? C20 C19 H19 121.2 . . ? C18 C19 H19 121.2 . . ? C19 C20 C21 123.03(16) . . ? C19 C20 N3 118.68(17) . . ? C21 C20 N3 118.27(17) . . ? C20 C21 C16 119.28(16) . . ? C20 C21 H21 120.4 . . ? C16 C21 H21 120.4 . . ? O3 C22 O4 123.36(16) . . ? O3 C22 C12 124.24(16) . . ? O4 C22 C12 112.39(14) . . ? O4 C23 H23A 109.5 . . ? O4 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O4 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C14 N1 C1 120.35(12) . . ? C14 N1 H1A 119.8 . . ? C1 N1 H1A 119.8 . . ? C9 N2 C15 130.98(13) . . ? C9 N2 C8 119.68(13) . . ? C15 N2 C8 109.11(13) . . ? O2 N3 O1 123.7(2) . . ? O2 N3 C20 117.98(19) . . ? O1 N3 C20 118.3(2) . . ? C22 O4 C23 116.67(15) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.43 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.503 _refine_diff_density_min -0.622 _refine_diff_density_rms 0.052 data_2a _database_code_depnum_ccdc_archive 'CCDC 782683' #TrackingRef 'CM-Sun-2a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Methyl 6,6-dimethyl-5,6-dihydroindolo[1,2-a]quinoxaline-3-carboxylate' ; _chemical_name_common ;'Methyl 6,6-dimethyl-5,6-dihydroindolo(1,2-a)quinoxaline-3- carboxylate' ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H36 N4 O4' _chemical_formula_weight 612.71 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' 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 1 c 1' _symmetry_space_group_name_hall 'P -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 10.1275(4) _cell_length_b 19.1023(7) _cell_length_c 8.0831(3) _cell_angle_alpha 90.00 _cell_angle_beta 106.1820(10) _cell_angle_gamma 90.00 _cell_volume 1501.79(10) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8125 _cell_measurement_theta_min 2.3498 _cell_measurement_theta_max 26.4047 _exptl_crystal_description Lump _exptl_crystal_colour 'Pale Yellow' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7180 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 13111 _diffrn_reflns_av_R_equivalents 0.0173 _diffrn_reflns_av_sigmaI/netI 0.0189 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 26.41 _reflns_number_total 4539 _reflns_number_gt 4461 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2010)' _computing_cell_refinement 'SAINT V7.34A (Bruker AXS, 2006)' _computing_data_reduction 'SAINT V7.34A (Bruker AXS, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material SHELXTL _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^)+(0.0719P)^2^+0.2161P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.2(8) _refine_ls_number_reflns 4539 _refine_ls_number_parameters 421 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0344 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.1044 _refine_ls_wR_factor_gt 0.0912 _refine_ls_goodness_of_fit_ref 1.150 _refine_ls_restrained_S_all 1.150 _refine_ls_shift/su_max 0.000 _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 C1 C 0.3878(2) 0.09805(9) -0.2073(3) 0.0168(4) Uani 1 1 d . . . C2 C 0.2690(2) 0.09525(9) -0.1312(3) 0.0149(4) Uani 1 1 d . . . C3 C 0.1499(2) 0.05818(10) -0.1807(3) 0.0181(4) Uani 1 1 d . . . H3 H 0.1247 0.0262 -0.2743 0.022 Uiso 1 1 calc R . . C4 C 0.06970(19) 0.07574(9) -0.0673(3) 0.0176(4) Uani 1 1 d . . . C5 C -0.0622(2) 0.05667(11) -0.0622(3) 0.0214(4) Uani 1 1 d . . . H5 H -0.1132 0.0228 -0.1405 0.026 Uiso 1 1 calc R . . C6 C -0.1180(2) 0.08735(11) 0.0574(3) 0.0238(4) Uani 1 1 d . . . H6 H -0.2076 0.0745 0.0616 0.029 Uiso 1 1 calc R . . C7 C -0.0435(2) 0.13730(11) 0.1726(3) 0.0229(4) Uani 1 1 d . . . H7 H -0.0843 0.1584 0.2529 0.027 Uiso 1 1 calc R . . C8 C 0.0879(2) 0.15662(10) 0.1724(3) 0.0193(4) Uani 1 1 d . . . H8 H 0.1378 0.1904 0.2518 0.023 Uiso 1 1 calc R . . C9 C 0.14527(18) 0.12531(9) 0.0530(3) 0.0151(4) Uani 1 1 d . . . C10 C 0.38148(18) 0.17983(9) 0.0913(2) 0.0150(4) Uani 1 1 d . . . C11 C 0.40209(19) 0.20956(10) 0.2540(3) 0.0170(4) Uani 1 1 d . . . H11 H 0.3405 0.1988 0.3200 0.020 Uiso 1 1 calc R . . C12 C 0.5115(2) 0.25466(10) 0.3208(3) 0.0176(4) Uani 1 1 d . . . H12 H 0.5223 0.2763 0.4296 0.021 Uiso 1 1 calc R . . C13 C 0.60566(19) 0.26800(9) 0.2270(3) 0.0158(4) Uani 1 1 d . . . C14 C 0.58924(19) 0.23632(9) 0.0681(3) 0.0161(4) Uani 1 1 d . . . H14 H 0.6560 0.2439 0.0074 0.019 Uiso 1 1 calc R . . C15 C 0.47624(19) 0.19356(9) -0.0039(2) 0.0153(4) Uani 1 1 d . . . C16 C 0.4933(2) 0.04064(10) -0.1298(3) 0.0227(4) Uani 1 1 d . . . H16A H 0.5729 0.0453 -0.1754 0.034 Uiso 1 1 calc R . . H16B H 0.4510 -0.0055 -0.1603 0.034 Uiso 1 1 calc R . . H16C H 0.5231 0.0455 -0.0041 0.034 Uiso 1 1 calc R . . C17 C 0.3378(2) 0.09004(10) -0.4024(3) 0.0213(4) Uani 1 1 d . . . H17A H 0.2689 0.1261 -0.4503 0.032 Uiso 1 1 calc R . . H17B H 0.2967 0.0436 -0.4312 0.032 Uiso 1 1 calc R . . H17C H 0.4157 0.0953 -0.4511 0.032 Uiso 1 1 calc R . . C18 C 0.72531(19) 0.31510(9) 0.2916(3) 0.0160(4) Uani 1 1 d . . . C19 C 0.8347(2) 0.39617(10) 0.5038(3) 0.0199(4) Uani 1 1 d . . . H19A H 0.9212 0.3700 0.5297 0.030 Uiso 1 1 calc R . . H19B H 0.8246 0.4178 0.6096 0.030 Uiso 1 1 calc R . . H19C H 0.8353 0.4327 0.4189 0.030 Uiso 1 1 calc R . . C20 C 0.13761(19) 0.40751(9) 1.1691(2) 0.0151(4) Uani 1 1 d . . . C21 C 0.2566(2) 0.41095(9) 1.0919(2) 0.0150(4) Uani 1 1 d . . . C22 C 0.37511(19) 0.44810(10) 1.1436(2) 0.0164(4) Uani 1 1 d . . . H22 H 0.3996 0.4802 1.2368 0.020 Uiso 1 1 calc R . . C23 C 0.45657(19) 0.42957(9) 1.0304(3) 0.0156(4) Uani 1 1 d . . . C24 C 0.5870(2) 0.45101(9) 1.0229(3) 0.0186(4) Uani 1 1 d . . . H24 H 0.6396 0.4830 1.1054 0.022 Uiso 1 1 calc R . . C25 C 0.63802(19) 0.42502(10) 0.8939(3) 0.0176(4) Uani 1 1 d . . . H25 H 0.7271 0.4385 0.8891 0.021 Uiso 1 1 calc R . . C26 C 0.5600(2) 0.37896(10) 0.7701(3) 0.0179(4) Uani 1 1 d . . . H26 H 0.5966 0.3626 0.6810 0.021 Uiso 1 1 calc R . . C27 C 0.4307(2) 0.35670(9) 0.7742(3) 0.0168(4) Uani 1 1 d . . . H27 H 0.3779 0.3259 0.6888 0.020 Uiso 1 1 calc R . . C28 C 0.38068(19) 0.38115(9) 0.9085(3) 0.0142(4) Uani 1 1 d . . . C29 C 0.14765(19) 0.32324(9) 0.8753(2) 0.0138(4) Uani 1 1 d . . . C30 C 0.15648(19) 0.27044(9) 0.7600(2) 0.0158(4) Uani 1 1 d . . . H30 H 0.2404 0.2632 0.7316 0.019 Uiso 1 1 calc R . . C31 C 0.04423(19) 0.22841(9) 0.6865(3) 0.0153(4) Uani 1 1 d . . . H31 H 0.0502 0.1937 0.6048 0.018 Uiso 1 1 calc R . . C32 C -0.07762(19) 0.23700(10) 0.7322(2) 0.0151(4) Uani 1 1 d . . . C33 C -0.08485(19) 0.28789(9) 0.8531(3) 0.0154(4) Uani 1 1 d . . . H33 H -0.1667 0.2925 0.8877 0.018 Uiso 1 1 calc R . . C34 C 0.02533(19) 0.33186(9) 0.9237(2) 0.0146(4) Uani 1 1 d . . . C35 C 0.1713(2) 0.35502(11) 1.3186(3) 0.0232(4) Uani 1 1 d . . . H35A H 0.0921 0.3505 1.3650 0.035 Uiso 1 1 calc R . . H35B H 0.2510 0.3717 1.4094 0.035 Uiso 1 1 calc R . . H35C H 0.1925 0.3094 1.2770 0.035 Uiso 1 1 calc R . . C36 C 0.1099(2) 0.47969(10) 1.2337(3) 0.0211(4) Uani 1 1 d . . . H36A H 0.0979 0.5139 1.1402 0.032 Uiso 1 1 calc R . . H36B H 0.1879 0.4936 1.3303 0.032 Uiso 1 1 calc R . . H36C H 0.0263 0.4779 1.2719 0.032 Uiso 1 1 calc R . . C37 C -0.19869(19) 0.19177(10) 0.6609(3) 0.0162(4) Uani 1 1 d . . . C38 C -0.2892(2) 0.10039(10) 0.4675(3) 0.0233(5) Uani 1 1 d . . . H38A H -0.3027 0.0701 0.5592 0.035 Uiso 1 1 calc R . . H38B H -0.2660 0.0717 0.3790 0.035 Uiso 1 1 calc R . . H38C H -0.3740 0.1265 0.4157 0.035 Uiso 1 1 calc R . . N1 N 0.45051(17) 0.16783(8) -0.1709(2) 0.0166(3) Uani 1 1 d . . . H1 H 0.4711 0.1925 -0.2522 0.020 Uiso 1 1 calc R . . N2 N 0.27021(16) 0.13552(8) 0.0136(2) 0.0147(3) Uani 1 1 d . . . N3 N 0.01362(16) 0.38633(8) 1.0335(2) 0.0160(3) Uani 1 1 d . . . H3A H -0.0656 0.4075 1.0223 0.019 Uiso 1 1 calc R . . N4 N 0.25735(16) 0.36897(8) 0.9505(2) 0.0140(3) Uani 1 1 d . . . O1 O 0.81708(15) 0.32235(7) 0.2243(2) 0.0228(3) Uani 1 1 d . . . O2 O 0.72189(14) 0.34946(7) 0.43553(18) 0.0198(3) Uani 1 1 d . . . O3 O -0.30332(14) 0.19294(7) 0.70460(19) 0.0212(3) Uani 1 1 d . . . O4 O -0.17915(14) 0.14866(7) 0.53844(19) 0.0199(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 0.0156(9) 0.0168(8) 0.0190(10) -0.0004(7) 0.0065(8) -0.0005(7) C2 0.0162(9) 0.0133(8) 0.0156(9) 0.0015(7) 0.0049(7) 0.0026(7) C3 0.0185(9) 0.0179(8) 0.0179(10) -0.0002(8) 0.0049(8) 0.0000(7) C4 0.0162(9) 0.0178(8) 0.0183(10) 0.0033(7) 0.0041(8) -0.0006(7) C5 0.0162(9) 0.0243(9) 0.0222(11) 0.0023(8) 0.0026(8) -0.0046(8) C6 0.0145(9) 0.0318(10) 0.0251(11) 0.0035(9) 0.0057(8) -0.0050(8) C7 0.0171(10) 0.0313(10) 0.0221(11) 0.0024(9) 0.0085(9) 0.0011(8) C8 0.0167(9) 0.0214(9) 0.0206(10) 0.0005(8) 0.0065(8) -0.0024(7) C9 0.0118(9) 0.0161(8) 0.0168(10) 0.0056(7) 0.0029(8) -0.0004(7) C10 0.0117(9) 0.0143(8) 0.0180(10) 0.0028(7) 0.0025(8) 0.0006(7) C11 0.0132(9) 0.0221(8) 0.0174(10) 0.0027(7) 0.0072(8) 0.0002(7) C12 0.0182(9) 0.0203(9) 0.0145(9) -0.0012(7) 0.0046(8) 0.0007(7) C13 0.0142(9) 0.0160(8) 0.0170(10) 0.0029(7) 0.0036(7) 0.0013(7) C14 0.0145(9) 0.0168(8) 0.0181(10) 0.0023(7) 0.0063(8) 0.0000(7) C15 0.0166(9) 0.0148(8) 0.0151(9) 0.0021(7) 0.0054(7) 0.0028(7) C16 0.0212(10) 0.0198(9) 0.0289(11) 0.0035(8) 0.0097(9) 0.0044(7) C17 0.0220(10) 0.0241(9) 0.0201(10) -0.0027(8) 0.0095(8) -0.0029(8) C18 0.0152(9) 0.0161(8) 0.0167(10) 0.0036(7) 0.0043(8) 0.0017(7) C19 0.0189(10) 0.0190(9) 0.0216(11) -0.0034(8) 0.0054(8) -0.0041(7) C20 0.0148(9) 0.0188(8) 0.0114(9) -0.0019(7) 0.0031(7) -0.0003(7) C21 0.0170(9) 0.0140(8) 0.0134(9) 0.0003(7) 0.0031(7) 0.0021(7) C22 0.0157(9) 0.0174(8) 0.0161(10) -0.0018(7) 0.0043(8) -0.0012(7) C23 0.0153(9) 0.0148(8) 0.0158(10) 0.0021(7) 0.0028(7) 0.0005(7) C24 0.0166(9) 0.0180(8) 0.0206(10) 0.0007(8) 0.0041(8) -0.0016(7) C25 0.0128(9) 0.0192(8) 0.0207(11) 0.0026(7) 0.0044(8) -0.0012(7) C26 0.0179(10) 0.0189(9) 0.0190(10) 0.0007(7) 0.0088(8) 0.0014(7) C27 0.0175(9) 0.0176(8) 0.0142(9) -0.0005(7) 0.0028(8) -0.0013(7) C28 0.0128(8) 0.0141(8) 0.0163(10) 0.0030(7) 0.0050(7) 0.0014(7) C29 0.0130(9) 0.0144(8) 0.0130(9) 0.0028(7) 0.0021(7) -0.0005(7) C30 0.0135(9) 0.0170(8) 0.0175(10) 0.0019(7) 0.0050(8) 0.0015(7) C31 0.0169(9) 0.0142(8) 0.0153(9) -0.0001(7) 0.0052(8) 0.0015(7) C32 0.0139(9) 0.0163(8) 0.0136(9) 0.0030(7) 0.0017(7) 0.0002(7) C33 0.0138(9) 0.0169(8) 0.0168(10) 0.0025(7) 0.0064(7) 0.0004(7) C34 0.0152(9) 0.0165(8) 0.0124(9) 0.0013(7) 0.0044(7) 0.0023(7) C35 0.0211(10) 0.0291(10) 0.0209(11) 0.0064(8) 0.0082(8) 0.0010(8) C36 0.0197(9) 0.0219(9) 0.0226(11) -0.0079(8) 0.0074(8) -0.0003(8) C37 0.0157(9) 0.0173(8) 0.0155(10) 0.0020(7) 0.0042(8) 0.0012(7) C38 0.0188(10) 0.0203(9) 0.0290(12) -0.0062(8) 0.0036(9) -0.0055(8) N1 0.0205(8) 0.0160(7) 0.0148(8) 0.0012(6) 0.0076(7) -0.0032(6) N2 0.0131(7) 0.0166(7) 0.0151(8) 0.0009(6) 0.0052(6) 0.0003(6) N3 0.0134(7) 0.0180(7) 0.0165(8) -0.0052(6) 0.0041(6) 0.0012(6) N4 0.0135(7) 0.0146(7) 0.0144(8) 0.0000(6) 0.0047(6) -0.0002(6) O1 0.0187(7) 0.0282(7) 0.0231(8) -0.0029(6) 0.0084(6) -0.0052(6) O2 0.0164(7) 0.0234(7) 0.0204(8) -0.0051(6) 0.0064(6) -0.0048(5) O3 0.0154(7) 0.0275(7) 0.0222(8) -0.0052(6) 0.0079(6) -0.0049(6) O4 0.0165(7) 0.0204(6) 0.0233(8) -0.0076(6) 0.0062(6) -0.0047(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 C1 N1 1.471(2) . ? C1 C2 1.497(3) . ? C1 C17 1.523(3) . ? C1 C16 1.538(3) . ? C2 C3 1.359(3) . ? C2 N2 1.398(3) . ? C3 C4 1.425(3) . ? C3 H3 0.9500 . ? C4 C5 1.397(3) . ? C4 C9 1.419(3) . ? C5 C6 1.379(3) . ? C5 H5 0.9500 . ? C6 C7 1.398(3) . ? C6 H6 0.9500 . ? C7 C8 1.382(3) . ? C7 H7 0.9500 . ? C8 C9 1.393(3) . ? C8 H8 0.9500 . ? C9 N2 1.402(2) . ? C10 C11 1.394(3) . ? C10 N2 1.409(2) . ? C10 C15 1.412(3) . ? C11 C12 1.389(3) . ? C11 H11 0.9500 . ? C12 C13 1.397(3) . ? C12 H12 0.9500 . ? C13 C14 1.387(3) . ? C13 C18 1.483(3) . ? C14 C15 1.394(3) . ? C14 H14 0.9500 . ? C15 N1 1.392(2) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 O1 1.208(2) . ? C18 O2 1.345(2) . ? C19 O2 1.433(2) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 N3 1.474(2) . ? C20 C21 1.505(3) . ? C20 C36 1.528(3) . ? C20 C35 1.534(3) . ? C21 C22 1.356(3) . ? C21 N4 1.398(2) . ? C22 C23 1.437(3) . ? C22 H22 0.9500 . ? C23 C24 1.401(3) . ? C23 C28 1.412(3) . ? C24 C25 1.378(3) . ? C24 H24 0.9500 . ? C25 C26 1.400(3) . ? C25 H25 0.9500 . ? C26 C27 1.386(3) . ? C26 H26 0.9500 . ? C27 C28 1.400(3) . ? C27 H27 0.9500 . ? C28 N4 1.402(2) . ? C29 C30 1.393(3) . ? C29 C34 1.409(3) . ? C29 N4 1.411(2) . ? C30 C31 1.383(3) . ? C30 H30 0.9500 . ? C31 C32 1.393(3) . ? C31 H31 0.9500 . ? C32 C33 1.395(3) . ? C32 C37 1.479(2) . ? C33 C34 1.386(3) . ? C33 H33 0.9500 . ? C34 N3 1.394(2) . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 O3 1.207(2) . ? C37 O4 1.344(2) . ? C38 O4 1.437(2) . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? N1 H1 0.8800 . ? N3 H3A 0.8800 . ? 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 C2 107.57(15) . . ? N1 C1 C17 107.38(16) . . ? C2 C1 C17 110.41(16) . . ? N1 C1 C16 110.64(16) . . ? C2 C1 C16 110.69(15) . . ? C17 C1 C16 110.07(16) . . ? C3 C2 N2 109.47(17) . . ? C3 C2 C1 130.25(18) . . ? N2 C2 C1 120.28(16) . . ? C2 C3 C4 107.83(18) . . ? C2 C3 H3 126.1 . . ? C4 C3 H3 126.1 . . ? C5 C4 C9 119.45(19) . . ? C5 C4 C3 132.82(19) . . ? C9 C4 C3 107.62(17) . . ? C6 C5 C4 119.46(19) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C5 C6 C7 120.46(19) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C8 C7 C6 121.5(2) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C7 C8 C9 118.32(19) . . ? C7 C8 H8 120.8 . . ? C9 C8 H8 120.8 . . ? C8 C9 N2 132.49(18) . . ? C8 C9 C4 120.79(17) . . ? N2 C9 C4 106.59(17) . . ? C11 C10 N2 123.79(17) . . ? C11 C10 C15 119.52(16) . . ? N2 C10 C15 116.69(17) . . ? C12 C11 C10 120.89(18) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C11 C12 C13 119.53(18) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C14 C13 C12 119.96(17) . . ? C14 C13 C18 117.79(17) . . ? C12 C13 C18 122.25(18) . . ? C13 C14 C15 120.97(18) . . ? C13 C14 H14 119.5 . . ? C15 C14 H14 119.5 . . ? N1 C15 C14 121.45(17) . . ? N1 C15 C10 119.42(16) . . ? C14 C15 C10 119.01(17) . . ? C1 C16 H16A 109.5 . . ? C1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C1 C17 H17A 109.5 . . ? C1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O1 C18 O2 122.82(17) . . ? O1 C18 C13 124.52(18) . . ? O2 C18 C13 112.66(16) . . ? O2 C19 H19A 109.5 . . ? O2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N3 C20 C21 108.56(15) . . ? N3 C20 C36 107.59(15) . . ? C21 C20 C36 110.28(16) . . ? N3 C20 C35 111.26(16) . . ? C21 C20 C35 109.09(16) . . ? C36 C20 C35 110.02(17) . . ? C22 C21 N4 110.23(17) . . ? C22 C21 C20 129.60(17) . . ? N4 C21 C20 120.09(16) . . ? C21 C22 C23 106.92(16) . . ? C21 C22 H22 126.5 . . ? C23 C22 H22 126.5 . . ? C24 C23 C28 119.87(18) . . ? C24 C23 C22 132.19(18) . . ? C28 C23 C22 107.94(16) . . ? C25 C24 C23 118.95(18) . . ? C25 C24 H24 120.5 . . ? C23 C24 H24 120.5 . . ? C24 C25 C26 120.77(18) . . ? C24 C25 H25 119.6 . . ? C26 C25 H25 119.6 . . ? C27 C26 C25 121.62(19) . . ? C27 C26 H26 119.2 . . ? C25 C26 H26 119.2 . . ? C26 C27 C28 117.71(18) . . ? C26 C27 H27 121.1 . . ? C28 C27 H27 121.1 . . ? C27 C28 N4 132.21(18) . . ? C27 C28 C23 120.99(18) . . ? N4 C28 C23 106.75(16) . . ? C30 C29 C34 119.72(17) . . ? C30 C29 N4 123.15(17) . . ? C34 C29 N4 117.12(16) . . ? C31 C30 C29 120.62(17) . . ? C31 C30 H30 119.7 . . ? C29 C30 H30 119.7 . . ? C30 C31 C32 120.03(17) . . ? C30 C31 H31 120.0 . . ? C32 C31 H31 120.0 . . ? C31 C32 C33 119.43(17) . . ? C31 C32 C37 121.82(17) . . ? C33 C32 C37 118.71(17) . . ? C34 C33 C32 121.16(17) . . ? C34 C33 H33 119.4 . . ? C32 C33 H33 119.4 . . ? C33 C34 N3 120.86(17) . . ? C33 C34 C29 118.95(16) . . ? N3 C34 C29 120.09(16) . . ? C20 C35 H35A 109.5 . . ? C20 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C20 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C20 C36 H36A 109.5 . . ? C20 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C20 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? O3 C37 O4 123.25(18) . . ? O3 C37 C32 125.11(18) . . ? O4 C37 C32 111.64(16) . . ? O4 C38 H38A 109.5 . . ? O4 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? O4 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C15 N1 C1 117.91(16) . . ? C15 N1 H1 121.0 . . ? C1 N1 H1 121.0 . . ? C2 N2 C9 108.44(15) . . ? C2 N2 C10 121.54(16) . . ? C9 N2 C10 129.96(16) . . ? C34 N3 C20 118.16(15) . . ? C34 N3 H3A 120.9 . . ? C20 N3 H3A 120.9 . . ? C21 N4 C28 108.12(15) . . ? C21 N4 C29 121.61(16) . . ? C28 N4 C29 130.26(16) . . ? C18 O2 C19 115.29(15) . . ? C37 O4 C38 115.47(16) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.41 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.431 _refine_diff_density_min -0.467 _refine_diff_density_rms 0.074