# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Ying Cheng' _publ_contact_author_email YCHENG2@BNU.EDU.CN _publ_section_title ; Synthesis of Novel and Versatile Synthetic Intermediates from the Reaction of Benzoimidazole and Triazole Carbenes with Ketenimines and their Application in the Construction of Spiro-pyrroles ; loop_ _publ_author_name 'Ying Cheng' 'Yang-Guang Ma' 'Jun-Ming Mo' # Attachment '3g.cif' data_3g _database_code_depnum_ccdc_archive 'CCDC 740317' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; (E)-1,3-bis(4-bromobenzyl)-2-(3-methoxy-2-methyl-3-oxo-1- (phenylamino)prop-1-enyl)-1H-benzo(d)imidazol-3-ium tetrafluoroborate ; _chemical_melting_point ? _chemical_formula_moiety 'C32 H28 B Br2 F4 N3 O2' _chemical_formula_sum 'C32 H28 B Br2 F4 N3 O2' _chemical_formula_weight 733.20 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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 21/n 1' 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 10.8497(12) _cell_length_b 17.4399(18) _cell_length_c 16.2784(17) _cell_angle_alpha 90.00 _cell_angle_beta 98.769(3) _cell_angle_gamma 90.00 _cell_volume 3044.2(6) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 8132 _cell_measurement_theta_min 1.7 _cell_measurement_theta_max 27.9 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.600 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 2.723 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6698 _exptl_absorpt_correction_T_max 0.7359 _exptl_absorpt_process_details CrystalClear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 29525 _diffrn_reflns_av_R_equivalents 0.0535 _diffrn_reflns_av_sigmaI/netI 0.0506 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 27.89 _reflns_number_total 7233 _reflns_number_gt 5635 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear(Rigaku/MSC Inc., 2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CrystalStructure 3.7.0' _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^)+(0.0563P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0036(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7233 _refine_ls_number_parameters 441 _refine_ls_number_restraints 68 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1051 _refine_ls_wR_factor_gt 0.0963 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.069 _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 Br1 Br 0.29161(2) 0.703438(18) 0.316511(18) 0.03082(11) Uani 1 1 d . . . Br2 Br 1.33333(3) 0.552286(19) 0.519209(17) 0.03699(11) Uani 1 1 d . . . F1 F 0.5899(5) 0.5677(4) 0.9611(5) 0.047(3) Uani 0.677(12) 1 d PDU A 1 F2 F 0.7115(5) 0.6213(5) 0.8755(2) 0.0682(18) Uani 0.677(12) 1 d PDU A 1 F3 F 0.7995(4) 0.5547(3) 0.9831(3) 0.0569(15) Uani 0.677(12) 1 d PDU A 1 F4 F 0.7155(5) 0.6657(4) 1.0049(5) 0.091(3) Uani 0.677(12) 1 d PDU A 1 F1' F 0.5926(9) 0.5701(8) 0.9667(10) 0.038(6) Uani 0.323(12) 1 d PDU A 2 F2' F 0.7309(12) 0.5863(8) 0.8799(6) 0.069(4) Uani 0.323(12) 1 d PDU A 2 F3' F 0.7919(9) 0.5932(9) 1.0162(7) 0.082(5) Uani 0.323(12) 1 d PDU A 2 F4' F 0.6788(11) 0.6836(4) 0.9514(10) 0.071(3) Uani 0.323(12) 1 d PDU A 2 O1 O 0.89112(16) 0.53790(11) 0.31842(10) 0.0224(4) Uani 1 1 d . . . O2 O 0.99133(19) 0.64243(11) 0.28314(11) 0.0333(5) Uani 1 1 d . . . N1 N 0.71888(18) 0.44264(12) 0.20391(12) 0.0169(4) Uani 1 1 d . . . N2 N 0.87129(18) 0.36739(12) 0.25863(12) 0.0170(4) Uani 1 1 d . . . N3 N 0.9690(2) 0.42995(13) 0.10157(13) 0.0212(5) Uani 1 1 d . . . C1 C 0.8417(2) 0.42909(14) 0.21029(14) 0.0165(5) Uani 1 1 d . . . C2 C 0.6666(2) 0.38747(15) 0.24975(14) 0.0186(5) Uani 1 1 d . . . C3 C 0.7637(2) 0.34056(15) 0.28568(15) 0.0193(5) Uani 1 1 d . . . C4 C 0.7440(3) 0.27943(16) 0.33715(16) 0.0258(6) Uani 1 1 d . . . H4 H 0.8104 0.2476 0.3621 0.031 Uiso 1 1 calc R . . C5 C 0.6221(3) 0.26766(17) 0.34985(17) 0.0298(6) Uani 1 1 d . . . H5 H 0.6045 0.2273 0.3854 0.036 Uiso 1 1 calc R . . C6 C 0.5245(3) 0.31350(17) 0.31184(17) 0.0285(6) Uani 1 1 d . . . H6 H 0.4421 0.3026 0.3212 0.034 Uiso 1 1 calc R . . C7 C 0.5439(2) 0.37433(17) 0.26094(15) 0.0233(6) Uani 1 1 d . . . H7 H 0.4771 0.4054 0.2351 0.028 Uiso 1 1 calc R . . C8 C 0.6519(2) 0.50262(16) 0.15100(15) 0.0211(5) Uani 1 1 d . . . H8A H 0.5992 0.4777 0.1034 0.025 Uiso 1 1 calc R . . H8B H 0.7137 0.5350 0.1284 0.025 Uiso 1 1 calc R . . C9 C 0.5708(2) 0.55338(15) 0.19495(15) 0.0199(5) Uani 1 1 d . . . C10 C 0.4698(2) 0.58889(16) 0.14657(16) 0.0225(6) Uani 1 1 d . . . H10 H 0.4562 0.5814 0.0881 0.027 Uiso 1 1 calc R . . C11 C 0.3894(2) 0.63470(16) 0.18252(16) 0.0236(6) Uani 1 1 d . . . H11 H 0.3217 0.6596 0.1490 0.028 Uiso 1 1 calc R . . C12 C 0.4079(2) 0.64416(15) 0.26768(16) 0.0222(6) Uani 1 1 d . . . C13 C 0.5096(2) 0.61071(17) 0.31710(16) 0.0255(6) Uani 1 1 d . . . H13 H 0.5229 0.6184 0.3756 0.031 Uiso 1 1 calc R . . C14 C 0.5910(2) 0.56617(16) 0.28026(16) 0.0237(6) Uani 1 1 d . . . H14 H 0.6615 0.5440 0.3135 0.028 Uiso 1 1 calc R . . C15 C 0.9988(2) 0.33613(15) 0.28067(15) 0.0208(5) Uani 1 1 d . . . H15A H 1.0360 0.3291 0.2293 0.025 Uiso 1 1 calc R . . H15B H 0.9941 0.2852 0.3068 0.025 Uiso 1 1 calc R . . C16 C 1.0824(2) 0.38776(15) 0.33960(15) 0.0186(5) Uani 1 1 d . . . C17 C 1.0530(2) 0.40458(16) 0.41786(15) 0.0217(6) Uani 1 1 d . . . H17 H 0.9805 0.3828 0.4345 0.026 Uiso 1 1 calc R . . C18 C 1.1282(2) 0.45268(15) 0.47189(16) 0.0220(6) Uani 1 1 d . . . H18 H 1.1081 0.4639 0.5254 0.026 Uiso 1 1 calc R . . C19 C 1.2334(2) 0.48400(16) 0.44613(16) 0.0230(6) Uani 1 1 d . . . C20 C 1.2654(2) 0.46766(17) 0.36901(16) 0.0261(6) Uani 1 1 d . . . H20 H 1.3382 0.4893 0.3526 0.031 Uiso 1 1 calc R . . C21 C 1.1890(2) 0.41898(16) 0.31589(15) 0.0229(6) Uani 1 1 d . . . H21 H 1.2102 0.4070 0.2628 0.027 Uiso 1 1 calc R . . C22 C 0.9318(2) 0.46923(15) 0.16636(14) 0.0173(5) Uani 1 1 d . . . C23 C 0.9810(2) 0.53818(15) 0.19292(15) 0.0176(5) Uani 1 1 d . . . C24 C 0.9490(2) 0.57064(15) 0.27041(15) 0.0188(5) Uani 1 1 d . . . C25 C 1.0733(3) 0.57713(17) 0.14700(17) 0.0267(6) Uani 1 1 d . . . H25A H 1.1529 0.5496 0.1570 0.040 Uiso 1 1 calc R . . H25B H 1.0858 0.6301 0.1666 0.040 Uiso 1 1 calc R . . H25C H 1.0416 0.5771 0.0873 0.040 Uiso 1 1 calc R . . C26 C 0.9660(4) 0.6788(2) 0.35824(19) 0.0473(9) Uani 1 1 d . . . H26A H 0.8764 0.6765 0.3605 0.071 Uiso 1 1 calc R . . H26B H 0.9928 0.7325 0.3588 0.071 Uiso 1 1 calc R . . H26C H 1.0117 0.6521 0.4065 0.071 Uiso 1 1 calc R . . C27 C 0.9112(2) 0.36337(15) 0.06350(14) 0.0182(5) Uani 1 1 d . . . C28 C 0.7820(2) 0.35742(16) 0.04401(14) 0.0229(6) Uani 1 1 d . . . H28 H 0.7303 0.3993 0.0539 0.027 Uiso 1 1 calc R . . C29 C 0.7294(3) 0.28983(17) 0.01011(16) 0.0270(6) Uani 1 1 d . . . H29 H 0.6413 0.2848 -0.0005 0.032 Uiso 1 1 calc R . . C30 C 0.8032(3) 0.22975(17) -0.00852(16) 0.0294(6) Uani 1 1 d . . . H30 H 0.7664 0.1838 -0.0321 0.035 Uiso 1 1 calc R . . C31 C 0.9324(3) 0.23743(16) 0.00775(15) 0.0258(6) Uani 1 1 d . . . H31 H 0.9840 0.1969 -0.0062 0.031 Uiso 1 1 calc R . . C32 C 0.9863(2) 0.30385(15) 0.04418(15) 0.0218(6) Uani 1 1 d . . . H32 H 1.0745 0.3084 0.0558 0.026 Uiso 1 1 calc R . . B1 B 0.7003(3) 0.60489(19) 0.95467(17) 0.0276(7) Uani 1 1 d D . . H3 H 1.042(3) 0.4430(17) 0.0874(18) 0.029(8) Uiso 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 Br1 0.02549(17) 0.03419(19) 0.03393(17) -0.00856(13) 0.00828(12) 0.00383(12) Br2 0.0464(2) 0.0382(2) 0.02512(16) -0.00503(13) 0.00130(14) -0.01638(14) F1 0.032(4) 0.064(5) 0.044(4) -0.008(3) 0.009(3) -0.030(3) F2 0.055(3) 0.110(5) 0.036(2) 0.035(2) -0.0033(18) -0.027(3) F3 0.038(2) 0.063(3) 0.073(3) 0.030(2) 0.0167(18) 0.0135(18) F4 0.064(3) 0.091(4) 0.125(5) -0.084(4) 0.036(3) -0.033(3) F1' 0.035(9) 0.053(9) 0.027(6) 0.004(6) 0.007(5) -0.005(6) F2' 0.074(6) 0.084(7) 0.064(6) -0.019(5) 0.058(5) -0.008(5) F3' 0.063(5) 0.105(8) 0.065(6) 0.056(6) -0.033(4) -0.056(6) F4' 0.080(6) 0.034(4) 0.104(8) 0.001(5) 0.031(5) -0.007(4) O1 0.0250(10) 0.0248(10) 0.0177(8) -0.0013(8) 0.0043(8) -0.0043(8) O2 0.0532(13) 0.0228(11) 0.0262(10) -0.0062(9) 0.0140(9) -0.0109(10) N1 0.0156(10) 0.0205(11) 0.0151(9) 0.0001(8) 0.0037(8) -0.0001(8) N2 0.0170(10) 0.0192(11) 0.0146(9) 0.0002(8) 0.0020(8) 0.0003(8) N3 0.0212(12) 0.0239(12) 0.0202(11) -0.0049(9) 0.0087(9) -0.0044(9) C1 0.0180(12) 0.0183(13) 0.0131(11) -0.0032(9) 0.0015(10) -0.0009(10) C2 0.0192(12) 0.0193(13) 0.0172(11) -0.0023(10) 0.0026(10) -0.0025(10) C3 0.0230(13) 0.0194(13) 0.0159(11) -0.0011(10) 0.0042(10) -0.0027(10) C4 0.0321(15) 0.0235(14) 0.0217(13) 0.0011(11) 0.0040(12) -0.0044(12) C5 0.0374(16) 0.0262(15) 0.0276(14) 0.0003(12) 0.0107(13) -0.0107(13) C6 0.0244(14) 0.0364(17) 0.0263(14) -0.0036(13) 0.0090(12) -0.0114(13) C7 0.0191(13) 0.0309(15) 0.0201(12) -0.0035(11) 0.0033(10) -0.0042(11) C8 0.0205(13) 0.0263(15) 0.0161(11) 0.0011(11) 0.0020(10) 0.0034(11) C9 0.0184(12) 0.0226(14) 0.0189(12) -0.0001(10) 0.0037(10) 0.0009(10) C10 0.0220(13) 0.0262(15) 0.0189(12) 0.0008(11) 0.0014(11) 0.0022(11) C11 0.0217(13) 0.0230(14) 0.0261(13) 0.0036(11) 0.0040(11) 0.0034(11) C12 0.0220(13) 0.0174(13) 0.0283(13) 0.0000(11) 0.0071(11) -0.0023(11) C13 0.0268(14) 0.0296(15) 0.0199(12) -0.0044(12) 0.0028(11) 0.0012(12) C14 0.0209(13) 0.0295(15) 0.0201(12) -0.0005(11) 0.0008(11) 0.0035(11) C15 0.0208(13) 0.0208(14) 0.0207(12) -0.0013(11) 0.0029(11) 0.0051(10) C16 0.0185(12) 0.0181(13) 0.0179(11) 0.0027(10) -0.0016(10) 0.0051(10) C17 0.0189(13) 0.0284(15) 0.0182(12) 0.0028(11) 0.0043(10) 0.0047(11) C18 0.0244(13) 0.0252(14) 0.0167(11) -0.0011(11) 0.0038(10) 0.0044(11) C19 0.0263(14) 0.0209(14) 0.0204(12) 0.0005(11) -0.0007(11) -0.0018(11) C20 0.0237(14) 0.0333(16) 0.0223(13) 0.0032(12) 0.0062(11) -0.0060(12) C21 0.0248(14) 0.0280(15) 0.0170(12) 0.0009(11) 0.0064(11) 0.0008(12) C22 0.0147(12) 0.0242(14) 0.0130(11) 0.0051(10) 0.0022(9) 0.0035(10) C23 0.0165(12) 0.0205(13) 0.0156(11) 0.0018(10) 0.0020(10) 0.0005(10) C24 0.0186(13) 0.0200(13) 0.0170(11) 0.0006(10) 0.0004(10) -0.0011(10) C25 0.0326(15) 0.0240(15) 0.0250(13) -0.0014(12) 0.0089(12) -0.0079(12) C26 0.084(3) 0.0304(18) 0.0332(16) -0.0144(14) 0.0281(18) -0.0160(18) C27 0.0232(13) 0.0207(13) 0.0113(10) -0.0003(10) 0.0044(10) -0.0023(11) C28 0.0247(14) 0.0292(15) 0.0146(11) -0.0013(11) 0.0024(10) 0.0009(12) C29 0.0242(14) 0.0365(17) 0.0188(12) 0.0001(12) -0.0014(11) -0.0056(12) C30 0.0419(17) 0.0265(15) 0.0189(12) -0.0030(12) 0.0018(12) -0.0084(13) C31 0.0379(16) 0.0218(14) 0.0186(12) 0.0015(11) 0.0075(12) 0.0030(12) C32 0.0241(14) 0.0244(14) 0.0178(12) 0.0011(11) 0.0057(11) -0.0007(11) B1 0.0228(16) 0.038(2) 0.0218(14) 0.0011(14) 0.0018(13) -0.0090(14) _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 Br1 C12 1.897(3) . ? Br2 C19 1.902(3) . ? F1 B1 1.380(5) . ? F2 B1 1.343(5) . ? F3 B1 1.410(4) . ? F4 B1 1.334(4) . ? F1' B1 1.357(7) . ? F2' B1 1.349(7) . ? F3' B1 1.315(6) . ? F4' B1 1.391(6) . ? O1 C24 1.217(3) . ? O2 C24 1.339(3) . ? O2 C26 1.440(3) . ? N1 C1 1.342(3) . ? N1 C2 1.391(3) . ? N1 C8 1.474(3) . ? N2 C1 1.343(3) . ? N2 C3 1.390(3) . ? N2 C15 1.480(3) . ? N3 C22 1.369(3) . ? N3 C27 1.417(3) . ? N3 H3 0.89(3) . ? C1 C22 1.473(3) . ? C2 C7 1.390(3) . ? C2 C3 1.390(4) . ? C3 C4 1.392(4) . ? C4 C5 1.385(4) . ? C4 H4 0.9500 . ? C5 C6 1.394(4) . ? C5 H5 0.9500 . ? C6 C7 1.382(4) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.503(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C14 1.391(3) . ? C9 C10 1.394(3) . ? C10 C11 1.378(4) . ? C10 H10 0.9500 . ? C11 C12 1.380(4) . ? C11 H11 0.9500 . ? C12 C13 1.391(4) . ? C13 C14 1.380(4) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.512(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C21 1.386(4) . ? C16 C17 1.391(3) . ? C17 C18 1.387(4) . ? C17 H17 0.9500 . ? C18 C19 1.386(4) . ? C18 H18 0.9500 . ? C19 C20 1.382(4) . ? C20 C21 1.392(4) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C23 1.359(4) . ? C23 C24 1.472(3) . ? C23 C25 1.501(4) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C32 1.385(4) . ? C27 C28 1.393(3) . ? C28 C29 1.387(4) . ? C28 H28 0.9500 . ? C29 C30 1.380(4) . ? C29 H29 0.9500 . ? C30 C31 1.392(4) . ? C30 H30 0.9500 . ? C31 C32 1.389(4) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? 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 C24 O2 C26 116.0(2) . . ? C1 N1 C2 108.6(2) . . ? C1 N1 C8 124.4(2) . . ? C2 N1 C8 126.8(2) . . ? C1 N2 C3 108.5(2) . . ? C1 N2 C15 124.6(2) . . ? C3 N2 C15 126.8(2) . . ? C22 N3 C27 125.7(2) . . ? C22 N3 H3 116.8(19) . . ? C27 N3 H3 116.7(19) . . ? N1 C1 N2 109.4(2) . . ? N1 C1 C22 127.1(2) . . ? N2 C1 C22 123.3(2) . . ? C7 C2 C3 121.8(2) . . ? C7 C2 N1 131.4(2) . . ? C3 C2 N1 106.7(2) . . ? C2 C3 N2 106.7(2) . . ? C2 C3 C4 121.9(2) . . ? N2 C3 C4 131.4(2) . . ? C5 C4 C3 116.1(3) . . ? C5 C4 H4 121.9 . . ? C3 C4 H4 121.9 . . ? C4 C5 C6 121.8(3) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C7 C6 C5 122.2(3) . . ? C7 C6 H6 118.9 . . ? C5 C6 H6 118.9 . . ? C6 C7 C2 116.2(3) . . ? C6 C7 H7 121.9 . . ? C2 C7 H7 121.9 . . ? N1 C8 C9 114.3(2) . . ? N1 C8 H8A 108.7 . . ? C9 C8 H8A 108.7 . . ? N1 C8 H8B 108.7 . . ? C9 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? C14 C9 C10 118.9(2) . . ? C14 C9 C8 123.7(2) . . ? C10 C9 C8 117.4(2) . . ? C11 C10 C9 120.8(2) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C12 119.4(2) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C11 C12 C13 120.8(2) . . ? C11 C12 Br1 118.78(19) . . ? C13 C12 Br1 120.39(19) . . ? C14 C13 C12 119.2(2) . . ? C14 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C13 C14 C9 120.7(2) . . ? C13 C14 H14 119.6 . . ? C9 C14 H14 119.6 . . ? N2 C15 C16 112.5(2) . . ? N2 C15 H15A 109.1 . . ? C16 C15 H15A 109.1 . . ? N2 C15 H15B 109.1 . . ? C16 C15 H15B 109.1 . . ? H15A C15 H15B 107.8 . . ? C21 C16 C17 119.3(2) . . ? C21 C16 C15 120.1(2) . . ? C17 C16 C15 120.5(2) . . ? C18 C17 C16 120.9(2) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C19 C18 C17 118.6(2) . . ? C19 C18 H18 120.7 . . ? C17 C18 H18 120.7 . . ? C20 C19 C18 121.7(2) . . ? C20 C19 Br2 119.9(2) . . ? C18 C19 Br2 118.33(19) . . ? C19 C20 C21 118.8(2) . . ? C19 C20 H20 120.6 . . ? C21 C20 H20 120.6 . . ? C16 C21 C20 120.7(2) . . ? C16 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C23 C22 N3 122.7(2) . . ? C23 C22 C1 121.6(2) . . ? N3 C22 C1 115.6(2) . . ? C22 C23 C24 118.7(2) . . ? C22 C23 C25 120.1(2) . . ? C24 C23 C25 121.0(2) . . ? O1 C24 O2 122.5(2) . . ? O1 C24 C23 125.6(2) . . ? O2 C24 C23 111.8(2) . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O2 C26 H26A 109.5 . . ? O2 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? O2 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C32 C27 C28 119.9(2) . . ? C32 C27 N3 118.5(2) . . ? C28 C27 N3 121.6(2) . . ? C29 C28 C27 119.5(3) . . ? C29 C28 H28 120.3 . . ? C27 C28 H28 120.3 . . ? C30 C29 C28 121.0(3) . . ? C30 C29 H29 119.5 . . ? C28 C29 H29 119.5 . . ? C29 C30 C31 119.1(3) . . ? C29 C30 H30 120.5 . . ? C31 C30 H30 120.5 . . ? C32 C31 C30 120.5(3) . . ? C32 C31 H31 119.7 . . ? C30 C31 H31 119.7 . . ? C27 C32 C31 119.8(2) . . ? C27 C32 H32 120.1 . . ? C31 C32 H32 120.1 . . ? F3' B1 F4 69.4(6) . . ? F3' B1 F2 126.5(6) . . ? F4 B1 F2 113.4(4) . . ? F3' B1 F2' 112.9(7) . . ? F4 B1 F2' 136.0(6) . . ? F2 B1 F2' 27.7(5) . . ? F3' B1 F1' 112.8(7) . . ? F4 B1 F1' 107.2(8) . . ? F2 B1 F1' 116.1(8) . . ? F2' B1 F1' 111.0(7) . . ? F3' B1 F1 115.7(6) . . ? F4 B1 F1 110.8(4) . . ? F2 B1 F1 112.3(4) . . ? F2' B1 F1 107.0(8) . . ? F1' B1 F1 4.1(10) . . ? F3' B1 F4' 106.5(5) . . ? F4 B1 F4' 40.9(4) . . ? F2 B1 F4' 78.0(5) . . ? F2' B1 F4' 105.4(5) . . ? F1' B1 F4' 107.7(7) . . ? F1 B1 F4' 108.9(7) . . ? F3' B1 F3 37.2(7) . . ? F4 B1 F3 106.0(3) . . ? F2 B1 F3 105.7(4) . . ? F2' B1 F3 82.3(6) . . ? F1' B1 F3 107.8(7) . . ? F1 B1 F3 108.1(4) . . ? F4' B1 F3 137.7(5) . . ? 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 C2 N1 C1 N2 -0.1(3) . . . . ? C8 N1 C1 N2 -175.6(2) . . . . ? C2 N1 C1 C22 174.5(2) . . . . ? C8 N1 C1 C22 -0.9(4) . . . . ? C3 N2 C1 N1 -0.9(3) . . . . ? C15 N2 C1 N1 -179.0(2) . . . . ? C3 N2 C1 C22 -175.8(2) . . . . ? C15 N2 C1 C22 6.1(4) . . . . ? C1 N1 C2 C7 -177.4(3) . . . . ? C8 N1 C2 C7 -2.1(4) . . . . ? C1 N1 C2 C3 1.1(3) . . . . ? C8 N1 C2 C3 176.4(2) . . . . ? C7 C2 C3 N2 177.0(2) . . . . ? N1 C2 C3 N2 -1.7(3) . . . . ? C7 C2 C3 C4 -2.2(4) . . . . ? N1 C2 C3 C4 179.1(2) . . . . ? C1 N2 C3 C2 1.6(3) . . . . ? C15 N2 C3 C2 179.6(2) . . . . ? C1 N2 C3 C4 -179.2(3) . . . . ? C15 N2 C3 C4 -1.2(4) . . . . ? C2 C3 C4 C5 0.6(4) . . . . ? N2 C3 C4 C5 -178.5(2) . . . . ? C3 C4 C5 C6 1.3(4) . . . . ? C4 C5 C6 C7 -1.5(4) . . . . ? C5 C6 C7 C2 -0.1(4) . . . . ? C3 C2 C7 C6 1.9(4) . . . . ? N1 C2 C7 C6 -179.7(3) . . . . ? C1 N1 C8 C9 -129.7(2) . . . . ? C2 N1 C8 C9 55.7(3) . . . . ? N1 C8 C9 C14 25.0(4) . . . . ? N1 C8 C9 C10 -154.7(2) . . . . ? C14 C9 C10 C11 -1.3(4) . . . . ? C8 C9 C10 C11 178.3(2) . . . . ? C9 C10 C11 C12 -1.3(4) . . . . ? C10 C11 C12 C13 2.7(4) . . . . ? C10 C11 C12 Br1 -177.0(2) . . . . ? C11 C12 C13 C14 -1.5(4) . . . . ? Br1 C12 C13 C14 178.3(2) . . . . ? C12 C13 C14 C9 -1.2(4) . . . . ? C10 C9 C14 C13 2.6(4) . . . . ? C8 C9 C14 C13 -177.0(3) . . . . ? C1 N2 C15 C16 70.3(3) . . . . ? C3 N2 C15 C16 -107.4(3) . . . . ? N2 C15 C16 C21 -118.8(3) . . . . ? N2 C15 C16 C17 61.0(3) . . . . ? C21 C16 C17 C18 0.7(4) . . . . ? C15 C16 C17 C18 -179.2(2) . . . . ? C16 C17 C18 C19 0.2(4) . . . . ? C17 C18 C19 C20 -0.9(4) . . . . ? C17 C18 C19 Br2 178.16(19) . . . . ? C18 C19 C20 C21 0.6(4) . . . . ? Br2 C19 C20 C21 -178.4(2) . . . . ? C17 C16 C21 C20 -1.0(4) . . . . ? C15 C16 C21 C20 178.9(2) . . . . ? C19 C20 C21 C16 0.4(4) . . . . ? C27 N3 C22 C23 -171.1(2) . . . . ? C27 N3 C22 C1 13.6(3) . . . . ? N1 C1 C22 C23 80.7(3) . . . . ? N2 C1 C22 C23 -105.3(3) . . . . ? N1 C1 C22 N3 -104.0(3) . . . . ? N2 C1 C22 N3 70.0(3) . . . . ? N3 C22 C23 C24 -171.1(2) . . . . ? C1 C22 C23 C24 3.9(3) . . . . ? N3 C22 C23 C25 4.5(4) . . . . ? C1 C22 C23 C25 179.5(2) . . . . ? C26 O2 C24 O1 0.9(4) . . . . ? C26 O2 C24 C23 -179.2(2) . . . . ? C22 C23 C24 O1 7.6(4) . . . . ? C25 C23 C24 O1 -167.9(2) . . . . ? C22 C23 C24 O2 -172.3(2) . . . . ? C25 C23 C24 O2 12.2(3) . . . . ? C22 N3 C27 C32 -137.3(3) . . . . ? C22 N3 C27 C28 44.0(4) . . . . ? C32 C27 C28 C29 4.0(4) . . . . ? N3 C27 C28 C29 -177.2(2) . . . . ? C27 C28 C29 C30 -3.3(4) . . . . ? C28 C29 C30 C31 0.5(4) . . . . ? C29 C30 C31 C32 1.6(4) . . . . ? C28 C27 C32 C31 -2.0(4) . . . . ? N3 C27 C32 C31 179.2(2) . . . . ? C30 C31 C32 C27 -0.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.89 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.590 _refine_diff_density_min -0.523 _refine_diff_density_rms 0.088 # Attachment '11d.cif' data_11d _database_code_depnum_ccdc_archive 'CCDC 740318' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; (E)-ethyl 2'-(1-methoxy-1-oxopropan-2-ylidene)-1,3-bis(4- methylbenzyl)-1'-phenyl-1,1',2',3-tetrahydrospiro(benzo(d)imidazole- 2,3'-pyrrole)-4'-carboxylate ; _chemical_melting_point ? _chemical_formula_moiety 'C39 H39 N3 O4' _chemical_formula_sum 'C39 H39 N3 O4' _chemical_formula_weight 613.73 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9376(10) _cell_length_b 13.3618(14) _cell_length_c 14.3300(16) _cell_angle_alpha 68.670(8) _cell_angle_beta 73.901(9) _cell_angle_gamma 72.586(8) _cell_volume 1660.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 3178 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 27.9 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.227 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 652 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9842 _exptl_absorpt_correction_T_max 0.9905 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 17084 _diffrn_reflns_av_R_equivalents 0.0473 _diffrn_reflns_av_sigmaI/netI 0.0574 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5832 _reflns_number_gt 4182 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CrystalStructure 3.7.0' _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^)+(0.1408P)^2^+0.3495P] 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 SHELXL _refine_ls_extinction_coef 0.016(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5832 _refine_ls_number_parameters 422 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1009 _refine_ls_R_factor_gt 0.0764 _refine_ls_wR_factor_ref 0.2439 _refine_ls_wR_factor_gt 0.2208 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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 0.4719(3) 0.29178(18) 0.55240(17) 0.0435(6) Uani 1 1 d . . . O2 O 0.6968(2) 0.20872(17) 0.49518(16) 0.0366(6) Uani 1 1 d . . . O3 O 0.6778(2) 0.53904(17) -0.00708(16) 0.0374(6) Uani 1 1 d . . . O4 O 0.8068(2) 0.51489(16) 0.10951(15) 0.0314(5) Uani 1 1 d . . . N1 N 0.6391(3) 0.42639(19) 0.32600(18) 0.0312(6) Uani 1 1 d . . . N2 N 0.8240(3) 0.29700(19) 0.27208(18) 0.0277(6) Uani 1 1 d . . . N3 N 0.5254(3) 0.26457(19) 0.22598(18) 0.0299(6) Uani 1 1 d . . . C1 C 0.6712(3) 0.3508(2) 0.2659(2) 0.0270(7) Uani 1 1 d . . . C2 C 0.7643(4) 0.4338(2) 0.3452(2) 0.0326(7) Uani 1 1 d . . . C3 C 0.7889(5) 0.5018(3) 0.3891(3) 0.0482(10) Uani 1 1 d . . . H3 H 0.7132 0.5576 0.4091 0.058 Uiso 1 1 calc R . . C4 C 0.9289(5) 0.4862(3) 0.4033(3) 0.0588(12) Uani 1 1 d . . . H4 H 0.9484 0.5322 0.4329 0.071 Uiso 1 1 calc R . . C5 C 1.0377(5) 0.4055(3) 0.3750(3) 0.0588(11) Uani 1 1 d . . . H5 H 1.1309 0.3960 0.3866 0.071 Uiso 1 1 calc R . . C6 C 1.0156(4) 0.3367(3) 0.3293(3) 0.0420(9) Uani 1 1 d . . . H6 H 1.0917 0.2809 0.3098 0.050 Uiso 1 1 calc R . . C7 C 0.8780(4) 0.3533(2) 0.3139(2) 0.0328(7) Uani 1 1 d . . . C8 C 0.4997(4) 0.5019(3) 0.3391(2) 0.0402(8) Uani 1 1 d . . . H8A H 0.4921 0.5277 0.3973 0.048 Uiso 1 1 calc R . . H8B H 0.4242 0.4599 0.3579 0.048 Uiso 1 1 calc R . . C9 C 0.4671(4) 0.6032(3) 0.2473(2) 0.0370(8) Uani 1 1 d . . . C10 C 0.3508(4) 0.6199(3) 0.2028(3) 0.0525(10) Uani 1 1 d . . . H10 H 0.2958 0.5653 0.2263 0.063 Uiso 1 1 calc R . . C11 C 0.3148(5) 0.7149(3) 0.1249(3) 0.0642(12) Uani 1 1 d . . . H11 H 0.2345 0.7250 0.0961 0.077 Uiso 1 1 calc R . . C12 C 0.3925(5) 0.7949(3) 0.0883(3) 0.0594(12) Uani 1 1 d . . . C13 C 0.5121(5) 0.7772(3) 0.1309(3) 0.0529(10) Uani 1 1 d . . . H13 H 0.5691 0.8307 0.1052 0.063 Uiso 1 1 calc R . . C14 C 0.5481(4) 0.6828(3) 0.2099(3) 0.0421(9) Uani 1 1 d . . . H14 H 0.6287 0.6724 0.2385 0.051 Uiso 1 1 calc R . . C15 C 0.3371(6) 0.9024(4) 0.0118(4) 0.0871(16) Uani 1 1 d . . . H15A H 0.3206 0.8875 -0.0457 0.131 Uiso 1 1 calc R . . H15B H 0.4080 0.9483 -0.0130 0.131 Uiso 1 1 calc R . . H15C H 0.2467 0.9412 0.0446 0.131 Uiso 1 1 calc R . . C16 C 0.9132(3) 0.2380(2) 0.2014(2) 0.0312(7) Uani 1 1 d . . . H16A H 1.0135 0.2442 0.1907 0.037 Uiso 1 1 calc R . . H16B H 0.8816 0.2744 0.1349 0.037 Uiso 1 1 calc R . . C17 C 0.9109(3) 0.1176(3) 0.2346(3) 0.0359(8) Uani 1 1 d . . . C18 C 0.8976(4) 0.0555(3) 0.3374(3) 0.0444(9) Uani 1 1 d . . . H18 H 0.8852 0.0895 0.3880 0.053 Uiso 1 1 calc R . . C19 C 0.9027(4) -0.0569(3) 0.3656(4) 0.0580(11) Uani 1 1 d . . . H19 H 0.8915 -0.0992 0.4357 0.070 Uiso 1 1 calc R . . C20 C 0.9242(4) -0.1070(3) 0.2918(4) 0.0629(12) Uani 1 1 d . . . C21 C 0.9363(6) -0.0456(4) 0.1910(4) 0.0757(15) Uani 1 1 d . . . H21 H 0.9485 -0.0799 0.1407 0.091 Uiso 1 1 calc R . . C22 C 0.9308(5) 0.0661(3) 0.1619(3) 0.0605(11) Uani 1 1 d . . . H22 H 0.9407 0.1077 0.0917 0.073 Uiso 1 1 calc R . . C23 C 0.9291(6) -0.2299(4) 0.3216(5) 0.0945(18) Uani 1 1 d . . . H23A H 0.9459 -0.2660 0.3916 0.142 Uiso 1 1 calc R . . H23B H 1.0071 -0.2627 0.2750 0.142 Uiso 1 1 calc R . . H23C H 0.8375 -0.2397 0.3171 0.142 Uiso 1 1 calc R . . C24 C 0.6458(3) 0.4029(2) 0.1558(2) 0.0277(7) Uani 1 1 d . . . C25 C 0.7079(3) 0.4914(2) 0.0772(2) 0.0294(7) Uani 1 1 d . . . C26 C 0.8666(4) 0.6091(2) 0.0424(2) 0.0354(8) Uani 1 1 d . . . H26A H 0.7892 0.6763 0.0283 0.042 Uiso 1 1 calc R . . H26B H 0.9199 0.5962 -0.0231 0.042 Uiso 1 1 calc R . . C27 C 0.9658(4) 0.6216(3) 0.0974(3) 0.0493(10) Uani 1 1 d . . . H27A H 0.9120 0.6322 0.1629 0.074 Uiso 1 1 calc R . . H27B H 1.0073 0.6856 0.0559 0.074 Uiso 1 1 calc R . . H27C H 1.0429 0.5551 0.1094 0.074 Uiso 1 1 calc R . . C28 C 0.5673(3) 0.3475(2) 0.1394(2) 0.0305(7) Uani 1 1 d . . . H28 H 0.5428 0.3633 0.0752 0.037 Uiso 1 1 calc R . . C29 C 0.5696(3) 0.2697(2) 0.3101(2) 0.0287(7) Uani 1 1 d . . . C30 C 0.5125(3) 0.2285(2) 0.4089(2) 0.0309(7) Uani 1 1 d . . . C31 C 0.3864(4) 0.1734(3) 0.4499(2) 0.0395(8) Uani 1 1 d . . . H31A H 0.3278 0.1977 0.3975 0.059 Uiso 1 1 calc R . . H31B H 0.3280 0.1937 0.5105 0.059 Uiso 1 1 calc R . . H31C H 0.4216 0.0933 0.4683 0.059 Uiso 1 1 calc R . . C32 C 0.5577(4) 0.2490(2) 0.4908(2) 0.0332(7) Uani 1 1 d . . . C33 C 0.7464(4) 0.2285(3) 0.5720(3) 0.0467(9) Uani 1 1 d . . . H33A H 0.7600 0.3041 0.5477 0.070 Uiso 1 1 calc R . . H33B H 0.8378 0.1766 0.5846 0.070 Uiso 1 1 calc R . . H33C H 0.6749 0.2180 0.6354 0.070 Uiso 1 1 calc R . . C34 C 0.4717(3) 0.1782(2) 0.2225(2) 0.0279(7) Uani 1 1 d . . . C35 C 0.5313(4) 0.0687(2) 0.2705(2) 0.0358(8) Uani 1 1 d . . . H35 H 0.6073 0.0509 0.3059 0.043 Uiso 1 1 calc R . . C36 C 0.4782(4) -0.0146(3) 0.2659(3) 0.0399(8) Uani 1 1 d . . . H36 H 0.5177 -0.0896 0.2988 0.048 Uiso 1 1 calc R . . C37 C 0.3681(4) 0.0116(3) 0.2135(2) 0.0379(8) Uani 1 1 d . . . H37 H 0.3314 -0.0453 0.2112 0.045 Uiso 1 1 calc R . . C38 C 0.3111(3) 0.1213(3) 0.1641(2) 0.0349(8) Uani 1 1 d . . . H38 H 0.2371 0.1389 0.1269 0.042 Uiso 1 1 calc R . . C39 C 0.3617(3) 0.2042(2) 0.1689(2) 0.0309(7) Uani 1 1 d . . . H39 H 0.3219 0.2790 0.1359 0.037 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0462(14) 0.0422(14) 0.0327(13) -0.0150(11) 0.0006(11) 0.0004(11) O2 0.0408(13) 0.0351(12) 0.0287(12) -0.0094(10) -0.0118(10) 0.0034(10) O3 0.0467(14) 0.0360(12) 0.0254(12) 0.0031(10) -0.0133(10) -0.0131(10) O4 0.0373(12) 0.0303(11) 0.0261(12) -0.0035(9) -0.0078(9) -0.0111(9) N1 0.0369(15) 0.0265(13) 0.0256(14) -0.0099(11) -0.0071(11) 0.0029(11) N2 0.0276(13) 0.0283(13) 0.0258(13) -0.0099(11) -0.0055(10) -0.0018(10) N3 0.0333(14) 0.0268(13) 0.0254(14) -0.0018(11) -0.0061(11) -0.0080(11) C1 0.0273(16) 0.0252(15) 0.0238(16) -0.0073(12) -0.0039(12) -0.0005(12) C2 0.047(2) 0.0240(16) 0.0221(16) -0.0028(13) -0.0115(14) -0.0013(14) C3 0.078(3) 0.0301(18) 0.035(2) -0.0091(15) -0.0232(19) 0.0002(17) C4 0.093(3) 0.043(2) 0.056(3) -0.0151(19) -0.048(2) -0.005(2) C5 0.069(3) 0.050(2) 0.070(3) -0.012(2) -0.046(2) -0.007(2) C6 0.046(2) 0.0369(18) 0.046(2) -0.0097(16) -0.0246(17) -0.0017(15) C7 0.0431(19) 0.0279(16) 0.0275(17) -0.0066(13) -0.0140(14) -0.0036(14) C8 0.044(2) 0.0313(18) 0.0294(18) -0.0076(14) -0.0027(15) 0.0079(15) C9 0.044(2) 0.0275(17) 0.0312(18) -0.0119(14) -0.0059(15) 0.0065(14) C10 0.057(2) 0.041(2) 0.053(2) -0.0121(18) -0.021(2) 0.0053(18) C11 0.077(3) 0.052(2) 0.064(3) -0.012(2) -0.041(2) 0.003(2) C12 0.087(3) 0.042(2) 0.042(2) -0.0106(18) -0.032(2) 0.011(2) C13 0.082(3) 0.0285(19) 0.042(2) -0.0114(17) -0.010(2) -0.0050(18) C14 0.057(2) 0.0282(17) 0.0342(19) -0.0098(15) -0.0140(16) 0.0055(16) C15 0.089(4) 0.079(3) 0.072(3) -0.011(3) -0.016(3) -0.003(3) C16 0.0309(16) 0.0299(16) 0.0276(17) -0.0099(14) -0.0006(13) -0.0025(13) C17 0.0258(16) 0.0332(17) 0.047(2) -0.0180(16) -0.0013(14) -0.0015(13) C18 0.0346(19) 0.0365(19) 0.056(2) -0.0042(17) -0.0136(17) -0.0079(15) C19 0.034(2) 0.044(2) 0.080(3) -0.002(2) -0.009(2) -0.0076(17) C20 0.042(2) 0.038(2) 0.101(4) -0.031(2) 0.005(2) -0.0043(17) C21 0.093(4) 0.062(3) 0.080(4) -0.046(3) 0.013(3) -0.024(3) C22 0.073(3) 0.059(3) 0.060(3) -0.034(2) 0.006(2) -0.029(2) C23 0.097(4) 0.061(3) 0.115(5) -0.034(3) 0.011(3) -0.023(3) C24 0.0279(16) 0.0295(16) 0.0210(15) -0.0046(13) -0.0048(12) -0.0035(13) C25 0.0298(16) 0.0259(15) 0.0285(17) -0.0067(13) -0.0055(13) -0.0027(13) C26 0.048(2) 0.0267(16) 0.0305(18) -0.0024(14) -0.0057(15) -0.0160(14) C27 0.064(3) 0.047(2) 0.043(2) -0.0080(17) -0.0099(18) -0.0283(19) C28 0.0321(17) 0.0301(16) 0.0224(16) -0.0017(13) -0.0047(13) -0.0054(13) C29 0.0272(16) 0.0266(16) 0.0254(16) -0.0042(13) -0.0059(12) 0.0002(12) C30 0.0317(17) 0.0238(15) 0.0264(16) -0.0023(13) -0.0022(13) -0.0003(13) C31 0.0398(19) 0.0405(19) 0.0289(18) -0.0035(15) 0.0009(14) -0.0115(15) C32 0.0405(19) 0.0252(16) 0.0228(16) -0.0013(13) -0.0042(14) -0.0005(14) C33 0.057(2) 0.049(2) 0.0323(19) -0.0119(17) -0.0186(17) -0.0009(18) C34 0.0272(16) 0.0286(16) 0.0233(16) -0.0067(13) -0.0002(12) -0.0056(12) C35 0.0397(19) 0.0283(17) 0.0322(18) -0.0035(14) -0.0095(14) -0.0021(14) C36 0.052(2) 0.0243(16) 0.0347(19) -0.0003(14) -0.0102(16) -0.0048(15) C37 0.047(2) 0.0286(17) 0.0357(19) -0.0076(15) -0.0020(15) -0.0127(15) C38 0.0310(17) 0.0379(18) 0.0349(18) -0.0103(15) -0.0075(14) -0.0065(14) C39 0.0319(17) 0.0271(16) 0.0265(16) -0.0045(13) -0.0013(13) -0.0049(13) _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 C32 1.220(4) . ? O2 C32 1.335(4) . ? O2 C33 1.454(4) . ? O3 C25 1.217(3) . ? O4 C25 1.350(4) . ? O4 C26 1.453(4) . ? N1 C2 1.384(4) . ? N1 C8 1.458(4) . ? N1 C1 1.467(4) . ? N2 C7 1.401(4) . ? N2 C16 1.448(4) . ? N2 C1 1.485(4) . ? N3 C28 1.390(4) . ? N3 C29 1.422(4) . ? N3 C34 1.430(4) . ? C1 C24 1.535(4) . ? C1 C29 1.548(4) . ? C2 C3 1.385(5) . ? C2 C7 1.405(4) . ? C3 C4 1.404(6) . ? C3 H3 0.9500 . ? C4 C5 1.368(6) . ? C4 H4 0.9500 . ? C5 C6 1.400(5) . ? C5 H5 0.9500 . ? C6 C7 1.384(5) . ? C6 H6 0.9500 . ? C8 C9 1.532(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C14 1.387(5) . ? C9 C10 1.394(5) . ? C10 C11 1.379(5) . ? C10 H10 0.9500 . ? C11 C12 1.370(6) . ? C11 H11 0.9500 . ? C12 C13 1.404(6) . ? C12 C15 1.511(6) . ? C13 C14 1.384(5) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.508(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C22 1.387(5) . ? C17 C18 1.396(5) . ? C18 C19 1.395(5) . ? C18 H18 0.9500 . ? C19 C20 1.385(6) . ? C19 H19 0.9500 . ? C20 C21 1.370(7) . ? C20 C23 1.528(6) . ? C21 C22 1.384(6) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C28 1.336(4) . ? C24 C25 1.459(4) . ? C26 C27 1.499(5) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28 0.9500 . ? C29 C30 1.344(4) . ? C30 C32 1.501(4) . ? C30 C31 1.513(4) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 C35 1.393(4) . ? C34 C39 1.396(4) . ? C35 C36 1.395(5) . ? C35 H35 0.9500 . ? C36 C37 1.385(5) . ? C36 H36 0.9500 . ? C37 C38 1.392(4) . ? C37 H37 0.9500 . ? C38 C39 1.377(4) . ? C38 H38 0.9500 . ? C39 H39 0.9500 . ? 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 C32 O2 C33 116.3(3) . . ? C25 O4 C26 116.5(2) . . ? C2 N1 C8 125.5(3) . . ? C2 N1 C1 110.5(2) . . ? C8 N1 C1 122.3(3) . . ? C7 N2 C16 123.0(3) . . ? C7 N2 C1 109.3(2) . . ? C16 N2 C1 121.0(2) . . ? C28 N3 C29 108.9(2) . . ? C28 N3 C34 123.0(2) . . ? C29 N3 C34 127.1(2) . . ? N1 C1 N2 101.8(2) . . ? N1 C1 C24 116.4(2) . . ? N2 C1 C24 112.9(2) . . ? N1 C1 C29 111.5(2) . . ? N2 C1 C29 113.9(2) . . ? C24 C1 C29 100.9(2) . . ? N1 C2 C3 131.2(3) . . ? N1 C2 C7 108.5(3) . . ? C3 C2 C7 120.3(3) . . ? C2 C3 C4 118.1(3) . . ? C2 C3 H3 120.9 . . ? C4 C3 H3 120.9 . . ? C5 C4 C3 120.9(3) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 122.0(4) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? C7 C6 C5 117.1(3) . . ? C7 C6 H6 121.4 . . ? C5 C6 H6 121.4 . . ? C6 C7 N2 129.8(3) . . ? C6 C7 C2 121.6(3) . . ? N2 C7 C2 108.5(3) . . ? N1 C8 C9 116.8(3) . . ? N1 C8 H8A 108.1 . . ? C9 C8 H8A 108.1 . . ? N1 C8 H8B 108.1 . . ? C9 C8 H8B 108.1 . . ? H8A C8 H8B 107.3 . . ? C14 C9 C10 118.6(3) . . ? C14 C9 C8 120.8(3) . . ? C10 C9 C8 120.5(3) . . ? C11 C10 C9 120.7(4) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C12 C11 C10 121.3(4) . . ? C12 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C11 C12 C13 118.2(3) . . ? C11 C12 C15 118.5(4) . . ? C13 C12 C15 123.0(4) . . ? C14 C13 C12 120.9(4) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C13 C14 C9 120.3(4) . . ? C13 C14 H14 119.9 . . ? C9 C14 H14 119.9 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N2 C16 C17 115.1(2) . . ? N2 C16 H16A 108.5 . . ? C17 C16 H16A 108.5 . . ? N2 C16 H16B 108.5 . . ? C17 C16 H16B 108.5 . . ? H16A C16 H16B 107.5 . . ? C22 C17 C18 119.3(3) . . ? C22 C17 C16 119.8(3) . . ? C18 C17 C16 120.7(3) . . ? C19 C18 C17 119.6(4) . . ? C19 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? C20 C19 C18 120.2(4) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C21 C20 C19 120.0(4) . . ? C21 C20 C23 119.1(5) . . ? C19 C20 C23 120.8(5) . . ? C20 C21 C22 120.4(4) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C21 C22 C17 120.5(4) . . ? C21 C22 H22 119.8 . . ? C17 C22 H22 119.8 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C28 C24 C25 124.3(3) . . ? C28 C24 C1 109.0(3) . . ? C25 C24 C1 126.4(3) . . ? O3 C25 O4 122.9(3) . . ? O3 C25 C24 126.1(3) . . ? O4 C25 C24 110.9(2) . . ? O4 C26 C27 106.2(2) . . ? O4 C26 H26A 110.5 . . ? C27 C26 H26A 110.5 . . ? O4 C26 H26B 110.5 . . ? C27 C26 H26B 110.5 . . ? H26A C26 H26B 108.7 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C24 C28 N3 113.0(3) . . ? C24 C28 H28 123.5 . . ? N3 C28 H28 123.5 . . ? C30 C29 N3 125.6(3) . . ? C30 C29 C1 126.4(3) . . ? N3 C29 C1 106.8(2) . . ? C29 C30 C32 120.8(3) . . ? C29 C30 C31 126.1(3) . . ? C32 C30 C31 112.5(3) . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? O1 C32 O2 123.2(3) . . ? O1 C32 C30 122.4(3) . . ? O2 C32 C30 114.2(3) . . ? O2 C33 H33A 109.5 . . ? O2 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? O2 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C35 C34 C39 120.4(3) . . ? C35 C34 N3 120.0(3) . . ? C39 C34 N3 119.6(3) . . ? C34 C35 C36 119.3(3) . . ? C34 C35 H35 120.4 . . ? C36 C35 H35 120.4 . . ? C37 C36 C35 120.2(3) . . ? C37 C36 H36 119.9 . . ? C35 C36 H36 119.9 . . ? C36 C37 C38 120.1(3) . . ? C36 C37 H37 119.9 . . ? C38 C37 H37 119.9 . . ? C39 C38 C37 120.2(3) . . ? C39 C38 H38 119.9 . . ? C37 C38 H38 119.9 . . ? C38 C39 C34 119.8(3) . . ? C38 C39 H39 120.1 . . ? C34 C39 H39 120.1 . . ? 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 C2 N1 C1 N2 11.9(3) . . . . ? C8 N1 C1 N2 177.7(2) . . . . ? C2 N1 C1 C24 -111.3(3) . . . . ? C8 N1 C1 C24 54.5(4) . . . . ? C2 N1 C1 C29 133.8(2) . . . . ? C8 N1 C1 C29 -60.5(3) . . . . ? C7 N2 C1 N1 -10.7(3) . . . . ? C16 N2 C1 N1 -162.8(2) . . . . ? C7 N2 C1 C24 114.8(3) . . . . ? C16 N2 C1 C24 -37.3(4) . . . . ? C7 N2 C1 C29 -130.9(3) . . . . ? C16 N2 C1 C29 77.0(3) . . . . ? C8 N1 C2 C3 7.5(5) . . . . ? C1 N1 C2 C3 172.7(3) . . . . ? C8 N1 C2 C7 -174.2(3) . . . . ? C1 N1 C2 C7 -8.9(3) . . . . ? N1 C2 C3 C4 176.8(3) . . . . ? C7 C2 C3 C4 -1.4(5) . . . . ? C2 C3 C4 C5 -0.3(6) . . . . ? C3 C4 C5 C6 1.1(6) . . . . ? C4 C5 C6 C7 -0.1(6) . . . . ? C5 C6 C7 N2 -178.9(3) . . . . ? C5 C6 C7 C2 -1.7(5) . . . . ? C16 N2 C7 C6 -25.0(5) . . . . ? C1 N2 C7 C6 -176.4(3) . . . . ? C16 N2 C7 C2 157.5(3) . . . . ? C1 N2 C7 C2 6.1(3) . . . . ? N1 C2 C7 C6 -176.1(3) . . . . ? C3 C2 C7 C6 2.5(5) . . . . ? N1 C2 C7 N2 1.7(3) . . . . ? C3 C2 C7 N2 -179.7(3) . . . . ? C2 N1 C8 C9 88.9(4) . . . . ? C1 N1 C8 C9 -74.6(4) . . . . ? N1 C8 C9 C14 -63.7(4) . . . . ? N1 C8 C9 C10 119.3(4) . . . . ? C14 C9 C10 C11 -1.7(5) . . . . ? C8 C9 C10 C11 175.3(3) . . . . ? C9 C10 C11 C12 0.7(6) . . . . ? C10 C11 C12 C13 1.0(6) . . . . ? C10 C11 C12 C15 -172.9(4) . . . . ? C11 C12 C13 C14 -1.8(6) . . . . ? C15 C12 C13 C14 171.8(4) . . . . ? C12 C13 C14 C9 0.8(5) . . . . ? C10 C9 C14 C13 0.9(5) . . . . ? C8 C9 C14 C13 -176.1(3) . . . . ? C7 N2 C16 C17 122.7(3) . . . . ? C1 N2 C16 C17 -89.1(3) . . . . ? N2 C16 C17 C22 149.6(3) . . . . ? N2 C16 C17 C18 -34.3(4) . . . . ? C22 C17 C18 C19 -0.8(5) . . . . ? C16 C17 C18 C19 -176.9(3) . . . . ? C17 C18 C19 C20 1.5(5) . . . . ? C18 C19 C20 C21 -1.9(6) . . . . ? C18 C19 C20 C23 -179.6(4) . . . . ? C19 C20 C21 C22 1.6(7) . . . . ? C23 C20 C21 C22 179.4(5) . . . . ? C20 C21 C22 C17 -0.9(7) . . . . ? C18 C17 C22 C21 0.6(6) . . . . ? C16 C17 C22 C21 176.7(4) . . . . ? N1 C1 C24 C28 -129.9(3) . . . . ? N2 C1 C24 C28 112.9(3) . . . . ? C29 C1 C24 C28 -9.1(3) . . . . ? N1 C1 C24 C25 55.7(4) . . . . ? N2 C1 C24 C25 -61.5(4) . . . . ? C29 C1 C24 C25 176.5(3) . . . . ? C26 O4 C25 O3 6.4(4) . . . . ? C26 O4 C25 C24 -174.0(2) . . . . ? C28 C24 C25 O3 13.4(5) . . . . ? C1 C24 C25 O3 -173.1(3) . . . . ? C28 C24 C25 O4 -166.2(3) . . . . ? C1 C24 C25 O4 7.4(4) . . . . ? C25 O4 C26 C27 176.8(3) . . . . ? C25 C24 C28 N3 177.8(3) . . . . ? C1 C24 C28 N3 3.3(3) . . . . ? C29 N3 C28 C24 4.9(3) . . . . ? C34 N3 C28 C24 -164.5(3) . . . . ? C28 N3 C29 C30 157.9(3) . . . . ? C34 N3 C29 C30 -33.3(5) . . . . ? C28 N3 C29 C1 -10.7(3) . . . . ? C34 N3 C29 C1 158.1(3) . . . . ? N1 C1 C29 C30 -32.6(4) . . . . ? N2 C1 C29 C30 81.9(4) . . . . ? C24 C1 C29 C30 -156.8(3) . . . . ? N1 C1 C29 N3 135.9(2) . . . . ? N2 C1 C29 N3 -109.6(3) . . . . ? C24 C1 C29 N3 11.7(3) . . . . ? N3 C29 C30 C32 -173.6(3) . . . . ? C1 C29 C30 C32 -7.1(4) . . . . ? N3 C29 C30 C31 -3.0(5) . . . . ? C1 C29 C30 C31 163.5(3) . . . . ? C33 O2 C32 O1 -6.3(4) . . . . ? C33 O2 C32 C30 178.8(3) . . . . ? C29 C30 C32 O1 123.5(3) . . . . ? C31 C30 C32 O1 -48.3(4) . . . . ? C29 C30 C32 O2 -61.6(4) . . . . ? C31 C30 C32 O2 126.6(3) . . . . ? C28 N3 C34 C35 128.4(3) . . . . ? C29 N3 C34 C35 -38.9(4) . . . . ? C28 N3 C34 C39 -50.2(4) . . . . ? C29 N3 C34 C39 142.5(3) . . . . ? C39 C34 C35 C36 -1.1(5) . . . . ? N3 C34 C35 C36 -179.7(3) . . . . ? C34 C35 C36 C37 0.5(5) . . . . ? C35 C36 C37 C38 0.8(5) . . . . ? C36 C37 C38 C39 -1.4(5) . . . . ? C37 C38 C39 C34 0.8(5) . . . . ? C35 C34 C39 C38 0.5(5) . . . . ? N3 C34 C39 C38 179.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.354 _refine_diff_density_min -0.455 _refine_diff_density_rms 0.074 # Attachment '17d.cif' data_080827a_0m _database_code_depnum_ccdc_archive 'CCDC 740319' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; (E)-methyl 2-((E)-1,3-bis(4-bromobenzyl)-4'-ethyl-5'-(2- methoxy-2-oxoethylidene)-1'-phenyl-1,3-dihydrospiro(benzo(d)imidazole- 2,3'-pyrrolidine)-2'-ylidene)propanoate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C39 H37 Br2 N3 O4' _chemical_formula_weight 771.54 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.31720(10) _cell_length_b 21.0352(2) _cell_length_c 17.9002(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.1870(10) _cell_angle_gamma 90.00 _cell_volume 3487.81(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6364 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 26.22 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.469 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1576 _exptl_absorpt_coefficient_mu 2.369 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5367 _exptl_absorpt_correction_T_max 0.6486 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 21027 _diffrn_reflns_av_R_equivalents 0.0198 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 27.51 _reflns_number_total 7987 _reflns_number_gt 5740 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0556P)^2^+2.6962P] 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 7987 _refine_ls_number_parameters 437 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0679 _refine_ls_R_factor_gt 0.0440 _refine_ls_wR_factor_ref 0.1235 _refine_ls_wR_factor_gt 0.1112 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 Br1 Br -0.00692(3) 0.635887(15) 0.25041(2) 0.05951(12) Uani 1 1 d . . . Br2 Br 0.79412(6) 1.12472(2) -0.09185(2) 0.08662(17) Uani 1 1 d . . . C1 C 0.1566(3) 0.68920(12) 0.27386(17) 0.0415(6) Uani 1 1 d . . . C2 C 0.2005(3) 0.72873(13) 0.21994(17) 0.0472(7) Uani 1 1 d . . . H2 H 0.1523 0.7290 0.1717 0.057 Uiso 1 1 calc R . . C3 C 0.3178(3) 0.76821(13) 0.23838(16) 0.0463(7) Uani 1 1 d . . . H3 H 0.3483 0.7950 0.2019 0.056 Uiso 1 1 calc R . . C4 C 0.3903(3) 0.76874(12) 0.30970(15) 0.0381(6) Uani 1 1 d . . . C5 C 0.3443(3) 0.72772(13) 0.36263(16) 0.0435(6) Uani 1 1 d . . . H5 H 0.3930 0.7269 0.4108 0.052 Uiso 1 1 calc R . . C6 C 0.2270(3) 0.68787(13) 0.34522(17) 0.0460(7) Uani 1 1 d . . . H6 H 0.1965 0.6607 0.3813 0.055 Uiso 1 1 calc R . . C7 C 0.5205(3) 0.81117(13) 0.33169(16) 0.0425(6) Uani 1 1 d . . . H7A H 0.4986 0.8388 0.3723 0.051 Uiso 1 1 calc R . . H7B H 0.6013 0.7845 0.3507 0.051 Uiso 1 1 calc R . . C8 C 0.6371(3) 0.82306(12) 0.21571(16) 0.0414(6) Uani 1 1 d . . . C9 C 0.6546(3) 0.76000(13) 0.19762(19) 0.0522(7) Uani 1 1 d . . . H9 H 0.6122 0.7278 0.2233 0.063 Uiso 1 1 calc R . . C10 C 0.7380(4) 0.74607(15) 0.1395(2) 0.0599(8) Uani 1 1 d . . . H10 H 0.7495 0.7039 0.1255 0.072 Uiso 1 1 calc R . . C11 C 0.8027(4) 0.79294(16) 0.10270(19) 0.0625(9) Uani 1 1 d . . . H11 H 0.8586 0.7823 0.0645 0.075 Uiso 1 1 calc R . . C12 C 0.7864(3) 0.85697(15) 0.12159(18) 0.0532(7) Uani 1 1 d . . . H12 H 0.8318 0.8890 0.0971 0.064 Uiso 1 1 calc R . . C13 C 0.7013(3) 0.87102(12) 0.17735(16) 0.0397(6) Uani 1 1 d . . . C14 C 0.7742(3) 0.98045(13) 0.20636(15) 0.0414(6) Uani 1 1 d . . . H14A H 0.8691 0.9630 0.2219 0.050 Uiso 1 1 calc R . . H14B H 0.7545 1.0128 0.2425 0.050 Uiso 1 1 calc R . . C15 C 0.7755(3) 1.01105(11) 0.12997(15) 0.0376(6) Uani 1 1 d . . . C16 C 0.9060(3) 1.02598(12) 0.10398(16) 0.0411(6) Uani 1 1 d . . . H16 H 0.9916 1.0137 0.1317 0.049 Uiso 1 1 calc R . . C17 C 0.9114(3) 1.05898(13) 0.03732(16) 0.0471(7) Uani 1 1 d . . . H17 H 0.9995 1.0692 0.0204 0.056 Uiso 1 1 calc R . . C18 C 0.7847(4) 1.07621(13) -0.00300(16) 0.0502(7) Uani 1 1 d . . . C19 C 0.6530(3) 1.06060(14) 0.01999(18) 0.0534(7) Uani 1 1 d . . . H19 H 0.5679 1.0719 -0.0089 0.064 Uiso 1 1 calc R . . C20 C 0.6491(3) 1.02786(13) 0.08660(16) 0.0456(6) Uani 1 1 d . . . H20 H 0.5606 1.0170 0.1025 0.055 Uiso 1 1 calc R . . C21 C 0.5839(3) 0.91946(11) 0.27269(15) 0.0351(5) Uani 1 1 d . . . C22 C 0.6494(3) 0.95112(12) 0.34656(15) 0.0354(5) Uani 1 1 d . . . C23 C 0.7314(3) 0.92557(13) 0.40540(16) 0.0416(6) Uani 1 1 d . . . C24 C 0.7482(4) 0.95140(16) 0.48435(17) 0.0578(8) Uani 1 1 d . . . H24A H 0.8366 0.9751 0.4927 0.087 Uiso 1 1 calc R . . H24B H 0.7506 0.9168 0.5195 0.087 Uiso 1 1 calc R . . H24C H 0.6682 0.9787 0.4913 0.087 Uiso 1 1 calc R . . C25 C 0.8162(3) 0.86736(13) 0.39724(17) 0.0427(6) Uani 1 1 d . . . C26 C 0.9634(4) 0.81220(18) 0.3176(2) 0.0766(11) Uani 1 1 d . . . H26A H 1.0521 0.8144 0.3501 0.115 Uiso 1 1 calc R . . H26B H 0.9839 0.8129 0.2662 0.115 Uiso 1 1 calc R . . H26C H 0.9138 0.7735 0.3271 0.115 Uiso 1 1 calc R . . C27 C 0.6532(3) 1.06568(12) 0.38810(15) 0.0409(6) Uani 1 1 d . . . C28 C 0.8010(3) 1.07475(14) 0.39757(17) 0.0506(7) Uani 1 1 d . . . H28 H 0.8617 1.0471 0.3754 0.061 Uiso 1 1 calc R . . C29 C 0.8577(4) 1.12572(17) 0.4407(2) 0.0670(10) Uani 1 1 d . . . H29 H 0.9572 1.1316 0.4480 0.080 Uiso 1 1 calc R . . C30 C 0.7691(5) 1.16713(18) 0.4723(2) 0.0793(12) Uani 1 1 d . . . H30 H 0.8083 1.2009 0.5012 0.095 Uiso 1 1 calc R . . C31 C 0.6213(5) 1.15900(18) 0.4613(2) 0.0763(11) Uani 1 1 d . . . H31 H 0.5607 1.1878 0.4819 0.092 Uiso 1 1 calc R . . C32 C 0.5636(4) 1.10788(16) 0.41964(18) 0.0570(8) Uani 1 1 d . . . H32 H 0.4641 1.1019 0.4129 0.068 Uiso 1 1 calc R . . C33 C 0.4876(3) 1.02233(12) 0.28298(15) 0.0376(6) Uani 1 1 d . . . C34 C 0.4534(3) 1.07851(12) 0.25076(16) 0.0426(6) Uani 1 1 d . . . H34 H 0.4947 1.1151 0.2730 0.051 Uiso 1 1 calc R . . C35 C 0.3542(3) 1.08499(12) 0.18214(16) 0.0424(6) Uani 1 1 d . . . C36 C 0.2704(5) 1.15694(18) 0.0864(2) 0.0766(11) Uani 1 1 d . . . H36A H 0.2990 1.1286 0.0486 0.115 Uiso 1 1 calc R . . H36B H 0.2838 1.2001 0.0711 0.115 Uiso 1 1 calc R . . H36C H 0.1705 1.1500 0.0926 0.115 Uiso 1 1 calc R . . C37 C 0.4382(3) 0.95694(11) 0.25927(16) 0.0380(6) Uani 1 1 d . . . H37 H 0.4006 0.9563 0.2060 0.046 Uiso 1 1 calc R . . C38 C 0.3217(3) 0.93413(14) 0.3090(2) 0.0551(8) Uani 1 1 d . . . H38A H 0.2941 0.8910 0.2947 0.066 Uiso 1 1 calc R . . H38B H 0.3641 0.9331 0.3610 0.066 Uiso 1 1 calc R . . C39 C 0.1882(4) 0.97446(19) 0.3040(3) 0.0777(11) Uani 1 1 d . . . H39A H 0.2136 1.0171 0.3194 0.117 Uiso 1 1 calc R . . H39B H 0.1220 0.9573 0.3363 0.117 Uiso 1 1 calc R . . H39C H 0.1435 0.9748 0.2531 0.117 Uiso 1 1 calc R . . N1 N 0.5642(2) 0.85017(9) 0.27147(13) 0.0399(5) Uani 1 1 d . . . N2 N 0.6670(2) 0.92985(10) 0.20730(12) 0.0368(5) Uani 1 1 d . . . N3 N 0.5902(2) 1.01309(10) 0.34564(13) 0.0380(5) Uani 1 1 d . . . O1 O 0.8732(2) 0.86613(10) 0.33169(14) 0.0576(6) Uani 1 1 d . . . O2 O 0.8399(3) 0.82701(11) 0.44445(14) 0.0695(7) Uani 1 1 d . . . O3 O 0.3573(2) 1.14507(9) 0.15660(13) 0.0578(6) Uani 1 1 d . . . O4 O 0.2799(2) 1.04490(10) 0.15003(13) 0.0611(6) 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 Br1 0.04528(17) 0.04783(18) 0.0839(3) 0.00576(16) -0.00006(15) -0.01257(13) Br2 0.1236(4) 0.0777(3) 0.0561(2) 0.02499(19) -0.0018(2) -0.0283(2) C1 0.0364(13) 0.0276(12) 0.0603(18) 0.0015(12) 0.0052(12) -0.0018(10) C2 0.0467(15) 0.0451(15) 0.0483(16) 0.0057(13) -0.0015(13) -0.0055(12) C3 0.0479(15) 0.0416(15) 0.0491(16) 0.0142(13) 0.0033(13) -0.0084(12) C4 0.0387(13) 0.0290(12) 0.0466(15) 0.0043(11) 0.0041(11) -0.0002(10) C5 0.0478(15) 0.0389(14) 0.0435(15) 0.0067(12) 0.0029(12) -0.0030(11) C6 0.0485(15) 0.0355(14) 0.0553(18) 0.0127(13) 0.0109(13) -0.0049(11) C7 0.0437(14) 0.0339(13) 0.0489(16) 0.0070(12) 0.0011(12) -0.0044(11) C8 0.0406(14) 0.0334(13) 0.0490(16) 0.0005(12) 0.0002(12) 0.0014(10) C9 0.0565(17) 0.0315(14) 0.068(2) -0.0003(13) 0.0029(15) 0.0003(12) C10 0.070(2) 0.0393(16) 0.069(2) -0.0111(15) 0.0033(17) 0.0109(15) C11 0.074(2) 0.058(2) 0.057(2) -0.0093(16) 0.0156(17) 0.0139(17) C12 0.0629(19) 0.0466(17) 0.0516(18) -0.0007(14) 0.0133(15) 0.0013(14) C13 0.0398(13) 0.0343(13) 0.0443(15) -0.0025(11) 0.0017(11) 0.0010(10) C14 0.0400(14) 0.0385(14) 0.0452(15) 0.0027(12) 0.0021(12) -0.0105(11) C15 0.0414(14) 0.0283(12) 0.0429(15) -0.0016(11) 0.0033(11) -0.0043(10) C16 0.0398(14) 0.0371(14) 0.0464(15) -0.0008(12) 0.0049(12) -0.0020(11) C17 0.0529(16) 0.0426(15) 0.0479(17) -0.0035(13) 0.0157(13) -0.0093(12) C18 0.073(2) 0.0379(15) 0.0397(15) 0.0021(12) 0.0041(14) -0.0141(14) C19 0.0537(17) 0.0492(17) 0.0534(18) 0.0028(14) -0.0114(14) -0.0041(13) C20 0.0413(14) 0.0447(15) 0.0503(17) 0.0031(13) 0.0019(12) -0.0067(12) C21 0.0334(12) 0.0268(12) 0.0448(14) 0.0032(10) 0.0032(11) -0.0024(9) C22 0.0321(12) 0.0324(12) 0.0425(14) 0.0016(11) 0.0072(10) -0.0018(9) C23 0.0397(14) 0.0392(14) 0.0452(15) 0.0048(12) 0.0007(12) -0.0034(11) C24 0.072(2) 0.0574(19) 0.0434(17) 0.0045(14) 0.0012(15) 0.0022(16) C25 0.0350(13) 0.0400(14) 0.0503(17) 0.0048(12) -0.0081(12) -0.0033(11) C26 0.059(2) 0.069(2) 0.100(3) -0.013(2) 0.002(2) 0.0292(18) C27 0.0476(15) 0.0356(13) 0.0387(14) -0.0021(11) 0.0005(12) -0.0026(11) C28 0.0491(16) 0.0468(16) 0.0541(18) -0.0002(13) -0.0032(14) -0.0042(13) C29 0.069(2) 0.058(2) 0.069(2) 0.0014(17) -0.0182(18) -0.0186(17) C30 0.110(3) 0.056(2) 0.066(2) -0.0182(18) -0.017(2) -0.014(2) C31 0.109(3) 0.059(2) 0.060(2) -0.0227(18) 0.006(2) 0.007(2) C32 0.064(2) 0.0539(18) 0.0532(19) -0.0120(15) 0.0085(15) 0.0026(15) C33 0.0314(12) 0.0347(13) 0.0464(15) -0.0042(11) 0.0028(11) -0.0004(10) C34 0.0417(14) 0.0307(13) 0.0538(17) -0.0039(12) -0.0023(12) -0.0007(10) C35 0.0399(14) 0.0318(13) 0.0546(17) -0.0016(12) 0.0005(12) 0.0017(10) C36 0.096(3) 0.058(2) 0.068(2) 0.0157(18) -0.028(2) -0.0104(19) C37 0.0310(12) 0.0296(12) 0.0522(16) 0.0000(11) -0.0012(11) -0.0012(10) C38 0.0380(14) 0.0417(16) 0.086(2) 0.0038(15) 0.0109(15) -0.0025(12) C39 0.0446(18) 0.079(3) 0.112(3) 0.012(2) 0.019(2) 0.0073(17) N1 0.0417(11) 0.0256(10) 0.0533(14) 0.0031(9) 0.0093(10) -0.0036(8) N2 0.0384(11) 0.0297(10) 0.0427(12) 0.0011(9) 0.0056(9) -0.0060(8) N3 0.0361(11) 0.0328(11) 0.0443(12) -0.0019(9) 0.0009(9) -0.0008(8) O1 0.0506(12) 0.0499(12) 0.0719(15) 0.0019(11) 0.0048(11) 0.0168(9) O2 0.0783(16) 0.0511(13) 0.0751(16) 0.0179(12) -0.0098(13) 0.0076(11) O3 0.0692(14) 0.0378(11) 0.0612(13) 0.0077(10) -0.0162(11) -0.0068(9) O4 0.0587(13) 0.0386(11) 0.0791(16) 0.0010(11) -0.0233(11) -0.0051(9) _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 Br1 C1 1.902(3) . ? Br2 C18 1.900(3) . ? C1 C2 1.370(4) . ? C1 C6 1.372(4) . ? C2 C3 1.384(4) . ? C2 H2 0.9300 . ? C3 C4 1.379(4) . ? C3 H3 0.9300 . ? C4 C5 1.383(4) . ? C4 C7 1.523(4) . ? C5 C6 1.386(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 N1 1.447(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.379(4) . ? C8 N1 1.389(4) . ? C8 C13 1.391(4) . ? C9 C10 1.396(5) . ? C9 H9 0.9300 . ? C10 C11 1.362(5) . ? C10 H10 0.9300 . ? C11 C12 1.401(4) . ? C11 H11 0.9300 . ? C12 C13 1.372(4) . ? C12 H12 0.9300 . ? C13 N2 1.399(3) . ? C14 N2 1.461(3) . ? C14 C15 1.512(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.384(4) . ? C15 C20 1.385(4) . ? C16 C17 1.386(4) . ? C16 H16 0.9300 . ? C17 C18 1.364(4) . ? C17 H17 0.9300 . ? C18 C19 1.376(4) . ? C19 C20 1.381(4) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 N1 1.469(3) . ? C21 N2 1.487(3) . ? C21 C22 1.546(4) . ? C21 C37 1.566(3) . ? C22 C23 1.345(4) . ? C22 N3 1.415(3) . ? C23 C25 1.473(4) . ? C23 C24 1.506(4) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 O2 1.201(3) . ? C25 O1 1.340(4) . ? C26 O1 1.450(4) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 C32 1.381(4) . ? C27 C28 1.382(4) . ? C27 N3 1.432(3) . ? C28 C29 1.391(4) . ? C28 H28 0.9300 . ? C29 C30 1.364(6) . ? C29 H29 0.9300 . ? C30 C31 1.381(6) . ? C30 H30 0.9300 . ? C31 C32 1.384(5) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? C33 C34 1.338(4) . ? C33 N3 1.407(3) . ? C33 C37 1.497(3) . ? C34 C35 1.462(4) . ? C34 H34 0.9300 . ? C35 O4 1.198(3) . ? C35 O3 1.345(3) . ? C36 O3 1.442(4) . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 C38 1.553(4) . ? C37 H37 0.9800 . ? C38 C39 1.501(4) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 0.9600 . ? 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 C2 C1 C6 121.3(2) . . ? C2 C1 Br1 119.7(2) . . ? C6 C1 Br1 119.0(2) . . ? C1 C2 C3 119.0(3) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C4 C3 C2 121.4(3) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C3 C4 C5 118.2(2) . . ? C3 C4 C7 122.8(2) . . ? C5 C4 C7 119.0(2) . . ? C4 C5 C6 121.2(3) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 118.9(3) . . ? C1 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? N1 C7 C4 114.8(2) . . ? N1 C7 H7A 108.6 . . ? C4 C7 H7A 108.6 . . ? N1 C7 H7B 108.6 . . ? C4 C7 H7B 108.6 . . ? H7A C7 H7B 107.5 . . ? C9 C8 N1 130.0(3) . . ? C9 C8 C13 120.9(3) . . ? N1 C8 C13 109.1(2) . . ? C8 C9 C10 117.8(3) . . ? C8 C9 H9 121.1 . . ? C10 C9 H9 121.1 . . ? C11 C10 C9 121.3(3) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C10 C11 C12 120.9(3) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C13 C12 C11 118.0(3) . . ? C13 C12 H12 121.0 . . ? C11 C12 H12 121.0 . . ? C12 C13 C8 121.0(3) . . ? C12 C13 N2 130.0(3) . . ? C8 C13 N2 108.9(2) . . ? N2 C14 C15 113.1(2) . . ? N2 C14 H14A 109.0 . . ? C15 C14 H14A 109.0 . . ? N2 C14 H14B 109.0 . . ? C15 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? C16 C15 C20 118.6(3) . . ? C16 C15 C14 119.6(2) . . ? C20 C15 C14 121.8(2) . . ? C15 C16 C17 121.2(3) . . ? C15 C16 H16 119.4 . . ? C17 C16 H16 119.4 . . ? C18 C17 C16 118.6(3) . . ? C18 C17 H17 120.7 . . ? C16 C17 H17 120.7 . . ? C17 C18 C19 121.8(3) . . ? C17 C18 Br2 118.1(2) . . ? C19 C18 Br2 120.1(2) . . ? C18 C19 C20 119.0(3) . . ? C18 C19 H19 120.5 . . ? C20 C19 H19 120.5 . . ? C19 C20 C15 120.8(3) . . ? C19 C20 H20 119.6 . . ? C15 C20 H20 119.6 . . ? N1 C21 N2 102.07(19) . . ? N1 C21 C22 118.5(2) . . ? N2 C21 C22 114.75(19) . . ? N1 C21 C37 113.09(19) . . ? N2 C21 C37 108.8(2) . . ? C22 C21 C37 99.8(2) . . ? C23 C22 N3 124.4(2) . . ? C23 C22 C21 129.5(2) . . ? N3 C22 C21 105.6(2) . . ? C22 C23 C25 121.3(3) . . ? C22 C23 C24 125.7(3) . . ? C25 C23 C24 113.0(2) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O2 C25 O1 122.8(3) . . ? O2 C25 C23 125.3(3) . . ? O1 C25 C23 111.8(2) . . ? O1 C26 H26A 109.5 . . ? O1 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? O1 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C32 C27 C28 120.0(3) . . ? C32 C27 N3 118.8(3) . . ? C28 C27 N3 121.2(3) . . ? C27 C28 C29 119.2(3) . . ? C27 C28 H28 120.4 . . ? C29 C28 H28 120.4 . . ? C30 C29 C28 120.7(3) . . ? C30 C29 H29 119.6 . . ? C28 C29 H29 119.6 . . ? C29 C30 C31 120.1(3) . . ? C29 C30 H30 120.0 . . ? C31 C30 H30 120.0 . . ? C30 C31 C32 119.8(4) . . ? C30 C31 H31 120.1 . . ? C32 C31 H31 120.1 . . ? C27 C32 C31 120.2(4) . . ? C27 C32 H32 119.9 . . ? C31 C32 H32 119.9 . . ? C34 C33 N3 125.1(2) . . ? C34 C33 C37 129.6(2) . . ? N3 C33 C37 105.1(2) . . ? C33 C34 C35 122.9(2) . . ? C33 C34 H34 118.5 . . ? C35 C34 H34 118.5 . . ? O4 C35 O3 122.0(3) . . ? O4 C35 C34 128.2(3) . . ? O3 C35 C34 109.8(2) . . ? O3 C36 H36A 109.5 . . ? O3 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? O3 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C33 C37 C38 109.5(2) . . ? C33 C37 C21 100.61(19) . . ? C38 C37 C21 113.9(2) . . ? C33 C37 H37 110.8 . . ? C38 C37 H37 110.8 . . ? C21 C37 H37 110.8 . . ? C39 C38 C37 114.7(3) . . ? C39 C38 H38A 108.6 . . ? C37 C38 H38A 108.6 . . ? C39 C38 H38B 108.6 . . ? C37 C38 H38B 108.6 . . ? H38A C38 H38B 107.6 . . ? 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 . . ? C8 N1 C7 120.1(2) . . ? C8 N1 C21 110.4(2) . . ? C7 N1 C21 126.6(2) . . ? C13 N2 C14 117.1(2) . . ? C13 N2 C21 109.4(2) . . ? C14 N2 C21 122.0(2) . . ? C33 N3 C22 111.6(2) . . ? C33 N3 C27 121.4(2) . . ? C22 N3 C27 124.6(2) . . ? C25 O1 C26 117.4(3) . . ? C35 O3 C36 115.4(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.622 _refine_diff_density_min -1.402 _refine_diff_density_rms 0.056 # Attachment '18e.cif' data_r90113g _database_code_depnum_ccdc_archive 'CCDC 740320' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; (E)-methyl 1,3-bis(4-bromobenzyl)-2'-(1-methoxy-1-oxopropan-2- ylidene)-5'-phenethyl-1'-phenyl-1,1',2',3- tetrahydrospiro(benzo(d)imidazole-2,3'-pyrrole)-4'-carboxylate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H39 Br2 N3 O4' _chemical_formula_weight 833.60 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 7.7608(16) _cell_length_b 18.522(4) _cell_length_c 26.266(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.70(3) _cell_angle_gamma 90.00 _cell_volume 3762.8(13) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 9198 _cell_measurement_theta_min 1.556 _cell_measurement_theta_max 27.916 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.471 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1704 _exptl_absorpt_coefficient_mu 2.203 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.4728 _exptl_absorpt_correction_T_max 0.9171 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'rigaku saturn' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 38112 _diffrn_reflns_av_R_equivalents 0.0542 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 25.02 _reflns_number_total 6631 _reflns_number_gt 5648 _reflns_threshold_expression >2sigma(I) _computing_data_collection crystalclear _computing_cell_refinement crystalclear _computing_data_reduction crystalclear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0467P)^2^+2.2958P] 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 SHELXL _refine_ls_extinction_coef 0.0023(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6631 _refine_ls_number_parameters 482 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0468 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.0981 _refine_ls_wR_factor_gt 0.0920 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.005 _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 Br1 Br 0.72436(4) 1.078094(18) 1.019622(10) 0.04137(12) Uani 1 1 d . . . Br2 Br 0.28160(5) 0.669537(17) 0.527752(12) 0.04745(13) Uani 1 1 d . . . O1 O 0.0250(2) 1.04766(10) 0.74213(7) 0.0286(4) Uani 1 1 d . . . O2 O 0.2357(2) 1.05804(10) 0.80528(6) 0.0242(4) Uani 1 1 d . . . O3 O 0.5756(2) 0.80448(10) 0.73033(7) 0.0287(4) Uani 1 1 d . . . O4 O 0.7043(3) 0.81992(10) 0.65752(7) 0.0335(5) Uani 1 1 d . . . N1 N 0.4941(2) 0.94431(11) 0.78245(7) 0.0169(4) Uani 1 1 d . . . N2 N 0.2696(3) 0.91935(11) 0.72483(7) 0.0191(4) Uani 1 1 d . . . N3 N 0.5440(3) 1.03834(11) 0.66976(7) 0.0201(4) Uani 1 1 d . . . C1 C 0.6743(3) 0.95075(14) 0.80137(9) 0.0214(5) Uani 1 1 d . . . H1A H 0.7344 0.9803 0.7780 0.026 Uiso 1 1 calc R . . H1B H 0.7272 0.9033 0.8026 0.026 Uiso 1 1 calc R . . C2 C 0.6941(3) 0.98414(14) 0.85408(9) 0.0204(5) Uani 1 1 d . . . C3 C 0.6070(3) 1.04760(14) 0.86439(10) 0.0248(6) Uani 1 1 d . . . H3 H 0.5405 1.0707 0.8382 0.030 Uiso 1 1 calc R . . C4 C 0.6180(4) 1.07669(15) 0.91318(10) 0.0294(6) Uani 1 1 d . . . H4 H 0.5593 1.1190 0.9198 0.035 Uiso 1 1 calc R . . C5 C 0.7175(3) 1.04195(14) 0.95185(10) 0.0259(6) Uani 1 1 d . . . C6 C 0.8103(3) 0.98082(14) 0.94220(9) 0.0245(6) Uani 1 1 d . . . H6 H 0.8810 0.9592 0.9682 0.029 Uiso 1 1 calc R . . C7 C 0.7972(3) 0.95178(14) 0.89344(9) 0.0222(5) Uani 1 1 d . . . H7 H 0.8583 0.9100 0.8869 0.027 Uiso 1 1 calc R . . C8 C 0.3796(3) 0.89896(13) 0.80540(9) 0.0174(5) Uani 1 1 d . . . C9 C 0.3827(3) 0.87122(13) 0.85403(9) 0.0219(5) Uani 1 1 d . . . H9 H 0.4766 0.8793 0.8777 0.026 Uiso 1 1 calc R . . C10 C 0.2403(4) 0.83030(13) 0.86703(10) 0.0249(6) Uani 1 1 d . . . H10 H 0.2408 0.8107 0.8996 0.030 Uiso 1 1 calc R . . C11 C 0.1003(3) 0.81872(14) 0.83248(10) 0.0263(6) Uani 1 1 d . . . H11 H 0.0063 0.7925 0.8423 0.032 Uiso 1 1 calc R . . C12 C 0.0976(3) 0.84601(13) 0.78254(10) 0.0222(5) Uani 1 1 d . . . H12 H 0.0038 0.8379 0.7589 0.027 Uiso 1 1 calc R . . C13 C 0.2382(3) 0.88515(12) 0.76981(9) 0.0178(5) Uani 1 1 d . . . C14 C 0.4411(3) 0.95206(12) 0.72753(8) 0.0165(5) Uani 1 1 d . . . C15 C 0.1555(3) 0.91752(13) 0.67852(9) 0.0223(5) Uani 1 1 d . . . H15A H 0.1672 0.9627 0.6605 0.027 Uiso 1 1 calc R . . H15B H 0.0373 0.9146 0.6878 0.027 Uiso 1 1 calc R . . C16 C 0.1862(3) 0.85595(14) 0.64226(9) 0.0218(5) Uani 1 1 d . . . C17 C 0.2257(3) 0.78678(15) 0.65967(10) 0.0283(6) Uani 1 1 d . . . H17 H 0.2342 0.7777 0.6946 0.034 Uiso 1 1 calc R . . C18 C 0.2531(4) 0.73077(15) 0.62622(10) 0.0311(6) Uani 1 1 d . . . H18 H 0.2795 0.6846 0.6384 0.037 Uiso 1 1 calc R . . C19 C 0.2402(3) 0.74512(15) 0.57425(10) 0.0292(6) Uani 1 1 d . . . C20 C 0.1984(3) 0.81284(16) 0.55571(10) 0.0295(6) Uani 1 1 d . . . H20 H 0.1884 0.8216 0.5207 0.035 Uiso 1 1 calc R . . C21 C 0.1713(3) 0.86801(15) 0.59005(9) 0.0254(6) Uani 1 1 d . . . H21 H 0.1426 0.9139 0.5777 0.031 Uiso 1 1 calc R . . C22 C 0.4279(3) 1.03134(13) 0.70859(9) 0.0186(5) Uani 1 1 d . . . C23 C 0.3089(3) 1.07892(13) 0.72087(9) 0.0211(5) Uani 1 1 d . . . C24 C 0.2736(4) 1.15255(15) 0.69774(12) 0.0385(7) Uani 1 1 d . . . H24A H 0.3077 1.1891 0.7225 0.058 Uiso 1 1 calc R . . H24B H 0.1524 1.1572 0.6877 0.058 Uiso 1 1 calc R . . H24C H 0.3383 1.1583 0.6684 0.058 Uiso 1 1 calc R . . C25 C 0.1749(3) 1.05785(13) 0.75644(9) 0.0214(5) Uani 1 1 d . . . C26 C 0.1140(3) 1.03616(15) 0.84137(10) 0.0282(6) Uani 1 1 d . . . H26A H 0.0186 1.0693 0.8397 0.042 Uiso 1 1 calc R . . H26B H 0.1706 1.0362 0.8753 0.042 Uiso 1 1 calc R . . H26C H 0.0722 0.9885 0.8330 0.042 Uiso 1 1 calc R . . C27 C 0.5650(3) 0.91995(13) 0.69200(9) 0.0184(5) Uani 1 1 d . . . C28 C 0.6126(3) 0.84381(14) 0.69611(9) 0.0222(5) Uani 1 1 d . . . C29 C 0.7539(4) 0.74446(15) 0.66059(13) 0.0429(8) Uani 1 1 d . . . H29A H 0.8149 0.7351 0.6932 0.064 Uiso 1 1 calc R . . H29B H 0.8275 0.7335 0.6340 0.064 Uiso 1 1 calc R . . H29C H 0.6523 0.7148 0.6566 0.064 Uiso 1 1 calc R . . C30 C 0.6178(3) 0.97138(13) 0.66026(9) 0.0193(5) Uani 1 1 d . . . C31 C 0.7258(3) 0.96324(14) 0.61607(9) 0.0214(5) Uani 1 1 d . . . H31A H 0.8124 0.9261 0.6235 0.026 Uiso 1 1 calc R . . H31B H 0.7848 1.0083 0.6102 0.026 Uiso 1 1 calc R . . C32 C 0.6086(3) 0.94239(16) 0.56794(9) 0.0289(6) Uani 1 1 d . . . H32A H 0.5214 0.9086 0.5776 0.035 Uiso 1 1 calc R . . H32B H 0.5495 0.9853 0.5544 0.035 Uiso 1 1 calc R . . C33 C 0.7059(3) 0.90879(14) 0.52652(9) 0.0228(6) Uani 1 1 d . . . C34 C 0.7118(4) 0.83412(16) 0.52177(10) 0.0323(7) Uani 1 1 d . . . H34 H 0.6562 0.8052 0.5443 0.039 Uiso 1 1 calc R . . C35 C 0.7995(4) 0.80230(18) 0.48389(11) 0.0427(8) Uani 1 1 d . . . H35 H 0.8021 0.7523 0.4809 0.051 Uiso 1 1 calc R . . C36 C 0.8827(4) 0.84435(19) 0.45073(11) 0.0426(8) Uani 1 1 d . . . H36 H 0.9410 0.8230 0.4251 0.051 Uiso 1 1 calc R . . C37 C 0.8797(4) 0.91852(18) 0.45541(10) 0.0358(7) Uani 1 1 d . . . H37 H 0.9372 0.9470 0.4330 0.043 Uiso 1 1 calc R . . C38 C 0.7920(3) 0.95085(15) 0.49309(10) 0.0275(6) Uani 1 1 d . . . H38 H 0.7908 1.0009 0.4960 0.033 Uiso 1 1 calc R . . C39 C 0.6129(3) 1.10528(13) 0.65189(9) 0.0187(5) Uani 1 1 d . . . C40 C 0.5653(3) 1.12953(14) 0.60282(9) 0.0235(5) Uani 1 1 d . . . H40 H 0.4842 1.1041 0.5819 0.028 Uiso 1 1 calc R . . C41 C 0.6389(3) 1.19180(14) 0.58510(10) 0.0254(6) Uani 1 1 d . . . H41 H 0.6075 1.2079 0.5521 0.031 Uiso 1 1 calc R . . C42 C 0.7585(3) 1.23017(14) 0.61606(11) 0.0274(6) Uani 1 1 d . . . H42 H 0.8094 1.2714 0.6037 0.033 Uiso 1 1 calc R . . C43 C 0.8025(3) 1.20722(14) 0.66534(11) 0.0287(6) Uani 1 1 d . . . H43 H 0.8805 1.2338 0.6866 0.034 Uiso 1 1 calc R . . C44 C 0.7302(3) 1.14423(14) 0.68339(10) 0.0248(6) Uani 1 1 d . . . H44 H 0.7608 1.1285 0.7165 0.030 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0500(2) 0.0508(2) 0.02256(17) -0.01447(13) -0.00159(13) 0.00584(15) Br2 0.0754(3) 0.0356(2) 0.03405(19) -0.01173(13) 0.02116(16) -0.00663(16) O1 0.0217(10) 0.0329(11) 0.0315(10) 0.0024(8) 0.0046(8) 0.0015(8) O2 0.0232(9) 0.0289(10) 0.0214(9) 0.0007(7) 0.0080(7) -0.0005(8) O3 0.0407(11) 0.0225(10) 0.0235(10) 0.0042(8) 0.0050(8) 0.0072(8) O4 0.0457(12) 0.0252(10) 0.0320(11) -0.0035(8) 0.0173(9) 0.0104(9) N1 0.0165(10) 0.0226(11) 0.0118(9) 0.0006(8) 0.0019(8) -0.0002(8) N2 0.0178(10) 0.0218(11) 0.0169(10) 0.0016(8) -0.0022(8) -0.0025(8) N3 0.0238(11) 0.0204(11) 0.0171(10) 0.0026(8) 0.0068(8) 0.0023(9) C1 0.0184(12) 0.0271(14) 0.0189(12) -0.0024(10) 0.0028(10) -0.0012(11) C2 0.0159(11) 0.0269(14) 0.0184(12) -0.0009(10) 0.0015(10) -0.0050(10) C3 0.0235(13) 0.0286(14) 0.0215(13) -0.0001(11) -0.0027(11) 0.0014(11) C4 0.0308(15) 0.0252(15) 0.0324(15) -0.0066(11) 0.0045(12) 0.0030(12) C5 0.0283(14) 0.0309(15) 0.0185(13) -0.0046(11) 0.0022(11) -0.0036(12) C6 0.0251(13) 0.0265(14) 0.0212(13) 0.0035(11) -0.0018(11) -0.0038(11) C7 0.0187(12) 0.0250(14) 0.0233(13) 0.0020(10) 0.0039(10) -0.0006(11) C8 0.0204(12) 0.0156(12) 0.0170(12) -0.0016(9) 0.0065(10) 0.0013(10) C9 0.0270(13) 0.0213(13) 0.0174(12) -0.0001(10) 0.0023(10) 0.0022(11) C10 0.0402(16) 0.0167(13) 0.0197(13) 0.0007(10) 0.0137(12) 0.0003(11) C11 0.0291(14) 0.0199(13) 0.0316(14) -0.0047(11) 0.0138(12) -0.0061(11) C12 0.0206(12) 0.0208(13) 0.0253(13) -0.0044(10) 0.0033(10) -0.0029(11) C13 0.0208(12) 0.0149(12) 0.0183(12) -0.0021(9) 0.0043(10) 0.0021(10) C14 0.0181(12) 0.0184(12) 0.0132(11) 0.0003(9) 0.0023(9) 0.0011(10) C15 0.0227(13) 0.0244(14) 0.0189(12) 0.0007(10) -0.0043(10) 0.0019(11) C16 0.0175(12) 0.0260(14) 0.0214(13) -0.0007(10) -0.0024(10) -0.0016(11) C17 0.0360(15) 0.0282(15) 0.0202(13) 0.0010(11) 0.0000(11) -0.0023(12) C18 0.0431(16) 0.0233(14) 0.0272(14) 0.0012(11) 0.0033(12) -0.0037(13) C19 0.0303(14) 0.0309(15) 0.0267(14) -0.0088(12) 0.0053(11) -0.0070(12) C20 0.0291(14) 0.0398(16) 0.0195(13) 0.0004(12) 0.0012(11) -0.0043(13) C21 0.0249(13) 0.0286(14) 0.0223(13) 0.0015(11) -0.0009(11) 0.0004(11) C22 0.0211(12) 0.0210(13) 0.0141(11) 0.0011(9) 0.0032(9) -0.0019(10) C23 0.0225(13) 0.0212(13) 0.0198(12) 0.0040(10) 0.0034(10) 0.0011(11) C24 0.0441(18) 0.0269(16) 0.0478(18) 0.0139(13) 0.0228(15) 0.0098(14) C25 0.0244(14) 0.0165(13) 0.0239(13) 0.0011(10) 0.0047(11) 0.0042(11) C26 0.0296(14) 0.0319(15) 0.0251(14) 0.0015(11) 0.0144(11) -0.0010(12) C27 0.0210(12) 0.0220(13) 0.0122(11) -0.0017(9) 0.0011(10) 0.0037(10) C28 0.0224(13) 0.0262(14) 0.0180(12) -0.0034(11) 0.0004(10) 0.0043(11) C29 0.0506(19) 0.0256(16) 0.054(2) -0.0077(14) 0.0150(16) 0.0143(14) C30 0.0191(12) 0.0242(13) 0.0144(12) -0.0008(10) 0.0010(10) 0.0011(10) C31 0.0201(12) 0.0280(14) 0.0164(12) -0.0009(10) 0.0033(10) 0.0008(11) C32 0.0214(13) 0.0468(17) 0.0180(13) -0.0047(12) -0.0004(11) 0.0030(12) C33 0.0186(12) 0.0325(15) 0.0166(12) -0.0038(10) -0.0024(10) -0.0002(11) C34 0.0405(17) 0.0330(16) 0.0225(14) 0.0004(11) -0.0039(12) -0.0042(13) C35 0.058(2) 0.0351(17) 0.0329(17) -0.0113(14) -0.0108(15) 0.0107(16) C36 0.0308(16) 0.071(2) 0.0254(15) -0.0203(15) -0.0024(13) 0.0194(16) C37 0.0260(14) 0.063(2) 0.0192(14) -0.0029(13) 0.0058(11) -0.0062(14) C38 0.0270(14) 0.0325(15) 0.0228(13) -0.0012(11) 0.0007(11) -0.0057(12) C39 0.0174(12) 0.0204(13) 0.0187(12) 0.0016(10) 0.0047(10) 0.0007(10) C40 0.0252(13) 0.0277(14) 0.0175(12) -0.0001(10) 0.0021(10) -0.0027(11) C41 0.0327(14) 0.0252(14) 0.0197(13) 0.0026(11) 0.0096(11) 0.0016(12) C42 0.0236(13) 0.0200(13) 0.0407(16) 0.0000(12) 0.0149(12) -0.0010(11) C43 0.0196(13) 0.0234(14) 0.0423(16) -0.0083(12) -0.0030(12) 0.0019(11) C44 0.0258(13) 0.0239(14) 0.0237(13) -0.0019(11) -0.0033(11) 0.0054(11) _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 Br1 C5 1.898(3) . ? Br2 C19 1.902(3) . ? O1 C25 1.207(3) . ? O2 C25 1.330(3) . ? O2 C26 1.449(3) . ? O3 C28 1.210(3) . ? O4 C28 1.360(3) . ? O4 C29 1.450(3) . ? N1 C8 1.395(3) . ? N1 C1 1.450(3) . ? N1 C14 1.474(3) . ? N2 C13 1.380(3) . ? N2 C15 1.445(3) . ? N2 C14 1.459(3) . ? N3 C30 1.397(3) . ? N3 C22 1.421(3) . ? N3 C39 1.444(3) . ? C1 C2 1.513(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C7 1.390(3) . ? C2 C3 1.394(4) . ? C3 C4 1.386(4) . ? C3 H3 0.9300 . ? C4 C5 1.383(4) . ? C4 H4 0.9300 . ? C5 C6 1.377(4) . ? C6 C7 1.385(4) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.375(3) . ? C8 C13 1.406(3) . ? C9 C10 1.405(4) . ? C9 H9 0.9300 . ? C10 C11 1.374(4) . ? C10 H10 0.9300 . ? C11 C12 1.404(4) . ? C11 H11 0.9300 . ? C12 C13 1.374(3) . ? C12 H12 0.9300 . ? C14 C27 1.515(3) . ? C14 C22 1.551(3) . ? C15 C16 1.517(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C21 1.385(3) . ? C16 C17 1.386(4) . ? C17 C18 1.387(4) . ? C17 H17 0.9300 . ? C18 C19 1.386(4) . ? C18 H18 0.9300 . ? C19 C20 1.375(4) . ? C20 C21 1.390(4) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C23 1.335(3) . ? C23 C25 1.506(3) . ? C23 C24 1.509(3) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 C30 1.352(3) . ? C27 C28 1.460(3) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 C31 1.494(3) . ? C31 C32 1.544(3) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 C33 1.509(3) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 C38 1.386(4) . ? C33 C34 1.390(4) . ? C34 C35 1.383(4) . ? C34 H34 0.9300 . ? C35 C36 1.369(5) . ? C35 H35 0.9300 . ? C36 C37 1.380(4) . ? C36 H36 0.9300 . ? C37 C38 1.383(4) . ? C37 H37 0.9300 . ? C38 H38 0.9300 . ? C39 C44 1.382(3) . ? C39 C40 1.386(3) . ? C40 C41 1.384(4) . ? C40 H40 0.9300 . ? C41 C42 1.380(4) . ? C41 H41 0.9300 . ? C42 C43 1.378(4) . ? C42 H42 0.9300 . ? C43 C44 1.395(4) . ? C43 H43 0.9300 . ? C44 H44 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 C25 O2 C26 115.6(2) . . ? C28 O4 C29 115.1(2) . . ? C8 N1 C1 122.14(19) . . ? C8 N1 C14 110.19(18) . . ? C1 N1 C14 120.72(19) . . ? C13 N2 C15 124.8(2) . . ? C13 N2 C14 111.94(19) . . ? C15 N2 C14 123.0(2) . . ? C30 N3 C22 109.91(19) . . ? C30 N3 C39 122.4(2) . . ? C22 N3 C39 125.8(2) . . ? N1 C1 C2 111.7(2) . . ? N1 C1 H1A 109.3 . . ? C2 C1 H1A 109.3 . . ? N1 C1 H1B 109.3 . . ? C2 C1 H1B 109.3 . . ? H1A C1 H1B 107.9 . . ? C7 C2 C3 118.6(2) . . ? C7 C2 C1 120.9(2) . . ? C3 C2 C1 120.5(2) . . ? C4 C3 C2 120.9(2) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C5 C4 C3 119.1(2) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C6 C5 C4 121.1(2) . . ? C6 C5 Br1 119.20(19) . . ? C4 C5 Br1 119.7(2) . . ? C5 C6 C7 119.3(2) . . ? C5 C6 H6 120.3 . . ? C7 C6 H6 120.3 . . ? C6 C7 C2 120.9(2) . . ? C6 C7 H7 119.5 . . ? C2 C7 H7 119.5 . . ? C9 C8 N1 131.5(2) . . ? C9 C8 C13 120.2(2) . . ? N1 C8 C13 108.2(2) . . ? C8 C9 C10 118.2(2) . . ? C8 C9 H9 120.9 . . ? C10 C9 H9 120.9 . . ? C11 C10 C9 121.2(2) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C10 C11 C12 120.7(2) . . ? C10 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C13 C12 C11 117.8(2) . . ? C13 C12 H12 121.1 . . ? C11 C12 H12 121.1 . . ? C12 C13 N2 130.6(2) . . ? C12 C13 C8 121.8(2) . . ? N2 C13 C8 107.6(2) . . ? N2 C14 N1 100.79(18) . . ? N2 C14 C27 115.44(19) . . ? N1 C14 C27 115.12(19) . . ? N2 C14 C22 109.96(19) . . ? N1 C14 C22 114.32(18) . . ? C27 C14 C22 101.69(19) . . ? N2 C15 C16 115.4(2) . . ? N2 C15 H15A 108.4 . . ? C16 C15 H15A 108.4 . . ? N2 C15 H15B 108.4 . . ? C16 C15 H15B 108.4 . . ? H15A C15 H15B 107.5 . . ? C21 C16 C17 118.3(2) . . ? C21 C16 C15 119.7(2) . . ? C17 C16 C15 122.0(2) . . ? C16 C17 C18 121.6(2) . . ? C16 C17 H17 119.2 . . ? C18 C17 H17 119.2 . . ? C19 C18 C17 118.5(3) . . ? C19 C18 H18 120.7 . . ? C17 C18 H18 120.7 . . ? C20 C19 C18 121.3(2) . . ? C20 C19 Br2 119.4(2) . . ? C18 C19 Br2 119.2(2) . . ? C19 C20 C21 119.0(2) . . ? C19 C20 H20 120.5 . . ? C21 C20 H20 120.5 . . ? C16 C21 C20 121.3(3) . . ? C16 C21 H21 119.4 . . ? C20 C21 H21 119.4 . . ? C23 C22 N3 127.2(2) . . ? C23 C22 C14 125.2(2) . . ? N3 C22 C14 106.71(19) . . ? C22 C23 C25 120.4(2) . . ? C22 C23 C24 127.3(2) . . ? C25 C23 C24 111.9(2) . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O1 C25 O2 123.9(2) . . ? O1 C25 C23 123.0(2) . . ? O2 C25 C23 112.9(2) . . ? O2 C26 H26A 109.5 . . ? O2 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? O2 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C30 C27 C28 129.7(2) . . ? C30 C27 C14 110.1(2) . . ? C28 C27 C14 120.2(2) . . ? O3 C28 O4 121.9(2) . . ? O3 C28 C27 124.2(2) . . ? O4 C28 C27 113.8(2) . . ? O4 C29 H29A 109.5 . . ? O4 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? O4 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C27 C30 N3 111.5(2) . . ? C27 C30 C31 128.7(2) . . ? N3 C30 C31 119.5(2) . . ? C30 C31 C32 109.3(2) . . ? C30 C31 H31A 109.8 . . ? C32 C31 H31A 109.8 . . ? C30 C31 H31B 109.8 . . ? C32 C31 H31B 109.8 . . ? H31A C31 H31B 108.3 . . ? C33 C32 C31 113.4(2) . . ? C33 C32 H32A 108.9 . . ? C31 C32 H32A 108.9 . . ? C33 C32 H32B 108.9 . . ? C31 C32 H32B 108.9 . . ? H32A C32 H32B 107.7 . . ? C38 C33 C34 118.8(2) . . ? C38 C33 C32 121.4(2) . . ? C34 C33 C32 119.8(2) . . ? C35 C34 C33 120.7(3) . . ? C35 C34 H34 119.6 . . ? C33 C34 H34 119.6 . . ? C36 C35 C34 120.1(3) . . ? C36 C35 H35 120.0 . . ? C34 C35 H35 120.0 . . ? C35 C36 C37 119.8(3) . . ? C35 C36 H36 120.1 . . ? C37 C36 H36 120.1 . . ? C36 C37 C38 120.5(3) . . ? C36 C37 H37 119.7 . . ? C38 C37 H37 119.7 . . ? C37 C38 C33 120.1(3) . . ? C37 C38 H38 120.0 . . ? C33 C38 H38 120.0 . . ? C44 C39 C40 120.0(2) . . ? C44 C39 N3 119.8(2) . . ? C40 C39 N3 120.2(2) . . ? C41 C40 C39 119.8(2) . . ? C41 C40 H40 120.1 . . ? C39 C40 H40 120.1 . . ? C42 C41 C40 120.5(2) . . ? C42 C41 H41 119.8 . . ? C40 C41 H41 119.8 . . ? C43 C42 C41 119.8(2) . . ? C43 C42 H42 120.1 . . ? C41 C42 H42 120.1 . . ? C42 C43 C44 120.1(2) . . ? C42 C43 H43 119.9 . . ? C44 C43 H43 119.9 . . ? C39 C44 C43 119.8(2) . . ? C39 C44 H44 120.1 . . ? C43 C44 H44 120.1 . . ? 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 C8 N1 C1 C2 -65.6(3) . . . . ? C14 N1 C1 C2 146.5(2) . . . . ? N1 C1 C2 C7 129.7(2) . . . . ? N1 C1 C2 C3 -49.3(3) . . . . ? C7 C2 C3 C4 -2.1(4) . . . . ? C1 C2 C3 C4 176.9(2) . . . . ? C2 C3 C4 C5 0.1(4) . . . . ? C3 C4 C5 C6 2.5(4) . . . . ? C3 C4 C5 Br1 -176.7(2) . . . . ? C4 C5 C6 C7 -3.1(4) . . . . ? Br1 C5 C6 C7 176.08(19) . . . . ? C5 C6 C7 C2 1.0(4) . . . . ? C3 C2 C7 C6 1.5(4) . . . . ? C1 C2 C7 C6 -177.5(2) . . . . ? C1 N1 C8 C9 23.1(4) . . . . ? C14 N1 C8 C9 174.0(2) . . . . ? C1 N1 C8 C13 -159.9(2) . . . . ? C14 N1 C8 C13 -9.0(3) . . . . ? N1 C8 C9 C10 175.6(2) . . . . ? C13 C8 C9 C10 -1.1(4) . . . . ? C8 C9 C10 C11 -0.7(4) . . . . ? C9 C10 C11 C12 1.7(4) . . . . ? C10 C11 C12 C13 -0.8(4) . . . . ? C11 C12 C13 N2 -178.4(2) . . . . ? C11 C12 C13 C8 -1.1(4) . . . . ? C15 N2 C13 C12 -3.2(4) . . . . ? C14 N2 C13 C12 -177.3(2) . . . . ? C15 N2 C13 C8 179.2(2) . . . . ? C14 N2 C13 C8 5.1(3) . . . . ? C9 C8 C13 C12 2.1(4) . . . . ? N1 C8 C13 C12 -175.4(2) . . . . ? C9 C8 C13 N2 179.9(2) . . . . ? N1 C8 C13 N2 2.4(3) . . . . ? C13 N2 C14 N1 -9.8(2) . . . . ? C15 N2 C14 N1 175.9(2) . . . . ? C13 N2 C14 C27 114.9(2) . . . . ? C15 N2 C14 C27 -59.4(3) . . . . ? C13 N2 C14 C22 -130.8(2) . . . . ? C15 N2 C14 C22 54.9(3) . . . . ? C8 N1 C14 N2 11.2(2) . . . . ? C1 N1 C14 N2 162.6(2) . . . . ? C8 N1 C14 C27 -113.7(2) . . . . ? C1 N1 C14 C27 37.7(3) . . . . ? C8 N1 C14 C22 129.1(2) . . . . ? C1 N1 C14 C22 -79.6(3) . . . . ? C13 N2 C15 C16 -89.6(3) . . . . ? C14 N2 C15 C16 83.9(3) . . . . ? N2 C15 C16 C21 -141.3(2) . . . . ? N2 C15 C16 C17 39.9(3) . . . . ? C21 C16 C17 C18 1.1(4) . . . . ? C15 C16 C17 C18 179.8(2) . . . . ? C16 C17 C18 C19 0.0(4) . . . . ? C17 C18 C19 C20 -1.1(4) . . . . ? C17 C18 C19 Br2 178.8(2) . . . . ? C18 C19 C20 C21 1.0(4) . . . . ? Br2 C19 C20 C21 -178.9(2) . . . . ? C17 C16 C21 C20 -1.2(4) . . . . ? C15 C16 C21 C20 -180.0(2) . . . . ? C19 C20 C21 C16 0.2(4) . . . . ? C30 N3 C22 C23 -165.5(2) . . . . ? C39 N3 C22 C23 29.8(4) . . . . ? C30 N3 C22 C14 4.1(2) . . . . ? C39 N3 C22 C14 -160.6(2) . . . . ? N2 C14 C22 C23 43.5(3) . . . . ? N1 C14 C22 C23 -69.0(3) . . . . ? C27 C14 C22 C23 166.3(2) . . . . ? N2 C14 C22 N3 -126.4(2) . . . . ? N1 C14 C22 N3 121.1(2) . . . . ? C27 C14 C22 N3 -3.6(2) . . . . ? N3 C22 C23 C25 168.9(2) . . . . ? C14 C22 C23 C25 1.1(4) . . . . ? N3 C22 C23 C24 -2.4(4) . . . . ? C14 C22 C23 C24 -170.2(3) . . . . ? C26 O2 C25 O1 7.4(3) . . . . ? C26 O2 C25 C23 -178.3(2) . . . . ? C22 C23 C25 O1 -107.2(3) . . . . ? C24 C23 C25 O1 65.3(3) . . . . ? C22 C23 C25 O2 78.4(3) . . . . ? C24 C23 C25 O2 -109.1(3) . . . . ? N2 C14 C27 C30 121.0(2) . . . . ? N1 C14 C27 C30 -122.1(2) . . . . ? C22 C14 C27 C30 2.0(2) . . . . ? N2 C14 C27 C28 -60.1(3) . . . . ? N1 C14 C27 C28 56.8(3) . . . . ? C22 C14 C27 C28 -179.1(2) . . . . ? C29 O4 C28 O3 -0.1(4) . . . . ? C29 O4 C28 C27 179.9(2) . . . . ? C30 C27 C28 O3 169.7(3) . . . . ? C14 C27 C28 O3 -8.9(4) . . . . ? C30 C27 C28 O4 -10.2(4) . . . . ? C14 C27 C28 O4 171.1(2) . . . . ? C28 C27 C30 N3 -178.4(2) . . . . ? C14 C27 C30 N3 0.4(3) . . . . ? C28 C27 C30 C31 7.6(4) . . . . ? C14 C27 C30 C31 -173.7(2) . . . . ? C22 N3 C30 C27 -2.9(3) . . . . ? C39 N3 C30 C27 162.4(2) . . . . ? C22 N3 C30 C31 171.7(2) . . . . ? C39 N3 C30 C31 -23.0(3) . . . . ? C27 C30 C31 C32 84.8(3) . . . . ? N3 C30 C31 C32 -88.8(3) . . . . ? C30 C31 C32 C33 -160.5(2) . . . . ? C31 C32 C33 C38 -81.8(3) . . . . ? C31 C32 C33 C34 97.4(3) . . . . ? C38 C33 C34 C35 -1.0(4) . . . . ? C32 C33 C34 C35 179.7(2) . . . . ? C33 C34 C35 C36 0.4(4) . . . . ? C34 C35 C36 C37 0.4(4) . . . . ? C35 C36 C37 C38 -0.6(4) . . . . ? C36 C37 C38 C33 -0.1(4) . . . . ? C34 C33 C38 C37 0.9(4) . . . . ? C32 C33 C38 C37 -179.8(2) . . . . ? C30 N3 C39 C44 -93.5(3) . . . . ? C22 N3 C39 C44 69.4(3) . . . . ? C30 N3 C39 C40 84.8(3) . . . . ? C22 N3 C39 C40 -112.3(3) . . . . ? C44 C39 C40 C41 1.6(4) . . . . ? N3 C39 C40 C41 -176.6(2) . . . . ? C39 C40 C41 C42 -0.4(4) . . . . ? C40 C41 C42 C43 -1.4(4) . . . . ? C41 C42 C43 C44 1.9(4) . . . . ? C40 C39 C44 C43 -1.1(4) . . . . ? N3 C39 C44 C43 177.2(2) . . . . ? C42 C43 C44 C39 -0.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.629 _refine_diff_density_min -0.572 _refine_diff_density_rms 0.071 # Attachment '19b-I.cif' data_19b-I _database_code_depnum_ccdc_archive 'CCDC 740321' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; (6E,8E)-methyl 6-(1-methoxy-1-oxopropan-2-ylidene)-7-(4- methoxyphenyl)-1,3,4-triphenyl-8-propylidene-1,2,4,7- tetraazaspiro(4.4)non-2-ene-9-carboxylate ; _chemical_melting_point ? _chemical_formula_moiety 'C39 H38 N4 O5' _chemical_formula_sum 'C39 H38 N4 O5' _chemical_formula_weight 642.73 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 21/n 1' 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 11.8253(19) _cell_length_b 18.626(3) _cell_length_c 15.232(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.810(3) _cell_angle_gamma 90.00 _cell_volume 3350.8(9) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 9250 _cell_measurement_theta_min 1.7 _cell_measurement_theta_max 27.9 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9782 _exptl_absorpt_correction_T_max 0.9832 _exptl_absorpt_process_details CrystalClear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'Rigaku Saturn CCD area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 33818 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0388 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 27.87 _reflns_number_total 7948 _reflns_number_gt 6507 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear(Rigaku/MSC Inc., 2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CrystalStructure 3.7.0' _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^)+(0.0675P)^2^+0.6414P] 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 7948 _refine_ls_number_parameters 438 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0494 _refine_ls_wR_factor_ref 0.1289 _refine_ls_wR_factor_gt 0.1193 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 O1 O 1.01910(8) 0.07681(5) 0.87399(7) 0.0260(2) Uani 1 1 d . . . O2 O 1.13255(8) 0.15066(6) 0.80099(7) 0.0272(2) Uani 1 1 d . . . O3 O 0.50246(8) 0.11064(6) 0.83512(7) 0.0259(2) Uani 1 1 d . . . O4 O 0.57574(8) 0.04834(5) 0.72502(7) 0.0263(2) Uani 1 1 d . . . O5 O 0.84739(11) 0.48697(6) 1.05464(7) 0.0380(3) Uani 1 1 d . . . N1 N 0.83709(9) 0.07558(6) 0.74455(7) 0.0192(2) Uani 1 1 d . . . N2 N 0.84117(9) 0.00449(6) 0.77357(7) 0.0197(2) Uani 1 1 d . . . N3 N 0.76028(9) 0.07120(6) 0.87707(7) 0.0177(2) Uani 1 1 d . . . N4 N 0.76868(9) 0.24551(6) 0.84304(7) 0.0189(2) Uani 1 1 d . . . C1 C 0.78235(10) 0.12312(7) 0.80620(8) 0.0174(3) Uani 1 1 d . . . C2 C 0.79835(11) 0.00425(7) 0.84995(8) 0.0185(3) Uani 1 1 d . . . C3 C 0.90215(11) 0.09555(8) 0.67459(8) 0.0196(3) Uani 1 1 d . . . C4 C 0.89617(12) 0.16442(8) 0.63774(9) 0.0237(3) Uani 1 1 d . . . H4 H 0.8464 0.1992 0.6602 0.028 Uiso 1 1 calc R . . C5 C 0.96326(13) 0.18188(9) 0.56823(10) 0.0293(3) Uani 1 1 d . . . H5 H 0.9587 0.2287 0.5436 0.035 Uiso 1 1 calc R . . C6 C 1.03641(13) 0.13221(9) 0.53435(10) 0.0328(4) Uani 1 1 d . . . H6 H 1.0822 0.1447 0.4871 0.039 Uiso 1 1 calc R . . C7 C 1.04178(13) 0.06384(9) 0.57051(10) 0.0312(4) Uani 1 1 d . . . H7 H 1.0920 0.0294 0.5478 0.037 Uiso 1 1 calc R . . C8 C 0.97503(12) 0.04494(8) 0.63929(9) 0.0243(3) Uani 1 1 d . . . H8 H 0.9787 -0.0024 0.6625 0.029 Uiso 1 1 calc R . . C9 C 0.78237(11) -0.06283(7) 0.89851(8) 0.0188(3) Uani 1 1 d . . . C10 C 0.86028(12) -0.11833(8) 0.89013(9) 0.0233(3) Uani 1 1 d . . . H10 H 0.9230 -0.1118 0.8543 0.028 Uiso 1 1 calc R . . C11 C 0.84703(13) -0.18296(8) 0.93359(10) 0.0263(3) Uani 1 1 d . . . H11 H 0.9008 -0.2204 0.9278 0.032 Uiso 1 1 calc R . . C12 C 0.75524(13) -0.19291(8) 0.98556(10) 0.0265(3) Uani 1 1 d . . . H12 H 0.7463 -0.2370 1.0157 0.032 Uiso 1 1 calc R . . C13 C 0.67627(12) -0.13812(8) 0.99341(9) 0.0259(3) Uani 1 1 d . . . H13 H 0.6129 -0.1452 1.0284 0.031 Uiso 1 1 calc R . . C14 C 0.68957(12) -0.07333(8) 0.95054(9) 0.0223(3) Uani 1 1 d . . . H14 H 0.6357 -0.0360 0.9565 0.027 Uiso 1 1 calc R . . C15 C 0.75900(11) 0.09123(7) 0.96831(8) 0.0187(3) Uani 1 1 d . . . C16 C 0.84092(11) 0.06462(8) 1.02833(9) 0.0222(3) Uani 1 1 d . . . H16 H 0.9029 0.0378 1.0083 0.027 Uiso 1 1 calc R . . C17 C 0.83204(12) 0.07733(8) 1.11751(9) 0.0264(3) Uani 1 1 d . . . H17 H 0.8868 0.0579 1.1586 0.032 Uiso 1 1 calc R . . C18 C 0.74339(13) 0.11838(9) 1.14707(9) 0.0290(3) Uani 1 1 d . . . H18 H 0.7367 0.1262 1.2082 0.035 Uiso 1 1 calc R . . C19 C 0.66504(14) 0.14777(9) 1.08694(10) 0.0301(3) Uani 1 1 d . . . H19 H 0.6063 0.1776 1.1069 0.036 Uiso 1 1 calc R . . C20 C 0.67151(12) 0.13406(8) 0.99759(9) 0.0241(3) Uani 1 1 d . . . H20 H 0.6167 0.1537 0.9567 0.029 Uiso 1 1 calc R . . C21 C 0.84790(11) 0.19046(7) 0.83672(8) 0.0178(3) Uani 1 1 d . . . C22 C 0.66070(11) 0.22975(7) 0.80170(8) 0.0181(3) Uani 1 1 d . . . C23 C 0.66840(11) 0.15559(7) 0.76393(8) 0.0183(3) Uani 1 1 d . . . H23 H 0.6761 0.1599 0.6991 0.022 Uiso 1 1 calc R . . C24 C 0.96200(11) 0.19896(8) 0.84394(9) 0.0214(3) Uani 1 1 d . . . C25 C 1.01849(13) 0.27197(8) 0.84533(12) 0.0335(4) Uani 1 1 d . . . H25A H 0.9734 0.3053 0.8082 0.050 Uiso 1 1 calc R . . H25B H 1.0945 0.2677 0.8230 0.050 Uiso 1 1 calc R . . H25C H 1.0241 0.2902 0.9058 0.050 Uiso 1 1 calc R . . C26 C 1.03687(11) 0.13521(8) 0.84251(9) 0.0214(3) Uani 1 1 d . . . C27 C 1.21112(12) 0.09200(9) 0.79310(11) 0.0310(3) Uani 1 1 d . . . H27A H 1.2265 0.0700 0.8509 0.046 Uiso 1 1 calc R . . H27B H 1.2819 0.1101 0.7706 0.046 Uiso 1 1 calc R . . H27C H 1.1783 0.0560 0.7524 0.046 Uiso 1 1 calc R . . C28 C 0.78801(11) 0.30854(7) 0.89576(9) 0.0189(3) Uani 1 1 d . . . C29 C 0.77405(11) 0.37622(7) 0.85948(9) 0.0204(3) Uani 1 1 d . . . H29 H 0.7517 0.3809 0.7990 0.024 Uiso 1 1 calc R . . C30 C 0.79237(12) 0.43765(8) 0.91052(9) 0.0233(3) Uani 1 1 d . . . H30 H 0.7813 0.4839 0.8853 0.028 Uiso 1 1 calc R . . C31 C 0.82710(12) 0.43056(8) 0.99871(10) 0.0256(3) Uani 1 1 d . . . C32 C 0.84210(13) 0.36228(8) 1.03509(10) 0.0285(3) Uani 1 1 d . . . H32 H 0.8663 0.3574 1.0952 0.034 Uiso 1 1 calc R . . C33 C 0.82201(12) 0.30158(8) 0.98440(9) 0.0248(3) Uani 1 1 d . . . H33 H 0.8313 0.2553 1.0099 0.030 Uiso 1 1 calc R . . C34 C 0.83381(18) 0.55767(9) 1.01866(13) 0.0466(5) Uani 1 1 d . . . H34A H 0.8857 0.5641 0.9711 0.070 Uiso 1 1 calc R . . H34B H 0.8508 0.5933 1.0648 0.070 Uiso 1 1 calc R . . H34C H 0.7556 0.5640 0.9955 0.070 Uiso 1 1 calc R . . C35 C 0.57278(11) 0.27486(7) 0.79604(9) 0.0208(3) Uani 1 1 d . . . H35 H 0.5820 0.3199 0.8248 0.025 Uiso 1 1 calc R . . C36 C 0.46092(11) 0.26091(8) 0.74843(10) 0.0251(3) Uani 1 1 d . . . H36A H 0.4623 0.2127 0.7210 0.030 Uiso 1 1 calc R . . H36B H 0.4489 0.2968 0.7009 0.030 Uiso 1 1 calc R . . C37 C 0.36278(13) 0.26471(10) 0.80948(11) 0.0356(4) Uani 1 1 d . . . H37A H 0.3725 0.2278 0.8551 0.053 Uiso 1 1 calc R . . H37B H 0.2914 0.2565 0.7756 0.053 Uiso 1 1 calc R . . H37C H 0.3613 0.3122 0.8370 0.053 Uiso 1 1 calc R . . C38 C 0.57165(11) 0.10458(7) 0.77989(9) 0.0201(3) Uani 1 1 d . . . C39 C 0.49683(13) -0.00915(8) 0.74082(11) 0.0305(3) Uani 1 1 d . . . H39A H 0.5078 -0.0257 0.8017 0.046 Uiso 1 1 calc R . . H39B H 0.5101 -0.0491 0.7007 0.046 Uiso 1 1 calc R . . H39C H 0.4192 0.0084 0.7307 0.046 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0207(5) 0.0211(5) 0.0363(6) 0.0014(4) 0.0027(4) 0.0018(4) O2 0.0153(5) 0.0265(6) 0.0401(6) 0.0011(4) 0.0065(4) 0.0028(4) O3 0.0199(5) 0.0260(6) 0.0324(5) -0.0002(4) 0.0066(4) -0.0012(4) O4 0.0223(5) 0.0228(5) 0.0339(6) -0.0076(4) 0.0029(4) -0.0054(4) O5 0.0547(8) 0.0240(6) 0.0341(6) -0.0086(5) -0.0095(5) -0.0029(5) N1 0.0215(6) 0.0149(6) 0.0220(6) 0.0006(4) 0.0081(4) 0.0018(4) N2 0.0203(6) 0.0158(6) 0.0233(6) 0.0010(4) 0.0044(4) 0.0001(4) N3 0.0191(5) 0.0151(6) 0.0193(5) -0.0007(4) 0.0047(4) 0.0006(4) N4 0.0147(5) 0.0176(6) 0.0243(6) -0.0012(4) -0.0001(4) 0.0013(4) C1 0.0146(6) 0.0174(7) 0.0203(6) -0.0010(5) 0.0038(5) 0.0010(5) C2 0.0158(6) 0.0177(7) 0.0220(6) -0.0017(5) 0.0020(5) -0.0007(5) C3 0.0166(6) 0.0234(7) 0.0188(6) 0.0001(5) 0.0024(5) -0.0028(5) C4 0.0207(7) 0.0243(7) 0.0265(7) 0.0024(6) 0.0045(5) 0.0010(6) C5 0.0271(8) 0.0316(9) 0.0293(8) 0.0091(6) 0.0032(6) -0.0032(6) C6 0.0286(8) 0.0433(10) 0.0274(8) 0.0040(7) 0.0116(6) -0.0044(7) C7 0.0278(8) 0.0357(9) 0.0313(8) -0.0037(7) 0.0114(6) 0.0016(7) C8 0.0230(7) 0.0247(8) 0.0257(7) -0.0010(6) 0.0064(5) 0.0015(6) C9 0.0196(6) 0.0180(7) 0.0186(6) -0.0015(5) 0.0003(5) -0.0018(5) C10 0.0223(7) 0.0216(7) 0.0266(7) -0.0009(6) 0.0057(5) 0.0017(6) C11 0.0279(8) 0.0197(7) 0.0315(8) 0.0012(6) 0.0041(6) 0.0043(6) C12 0.0306(8) 0.0209(7) 0.0280(7) 0.0049(6) 0.0025(6) -0.0031(6) C13 0.0260(7) 0.0249(8) 0.0273(7) 0.0012(6) 0.0075(6) -0.0039(6) C14 0.0211(7) 0.0216(7) 0.0245(7) 0.0001(5) 0.0034(5) -0.0001(5) C15 0.0199(6) 0.0168(7) 0.0196(6) -0.0018(5) 0.0038(5) -0.0032(5) C16 0.0200(7) 0.0206(7) 0.0261(7) -0.0025(5) 0.0010(5) -0.0005(5) C17 0.0279(7) 0.0259(8) 0.0248(7) -0.0012(6) -0.0040(6) -0.0042(6) C18 0.0349(8) 0.0315(8) 0.0207(7) -0.0059(6) 0.0022(6) -0.0061(7) C19 0.0330(8) 0.0297(8) 0.0281(8) -0.0059(6) 0.0081(6) 0.0048(6) C20 0.0245(7) 0.0248(8) 0.0234(7) -0.0005(6) 0.0034(5) 0.0048(6) C21 0.0169(6) 0.0152(7) 0.0214(6) 0.0011(5) 0.0024(5) 0.0017(5) C22 0.0168(6) 0.0193(7) 0.0183(6) 0.0012(5) 0.0020(5) -0.0021(5) C23 0.0156(6) 0.0196(7) 0.0198(6) 0.0000(5) 0.0016(5) 0.0009(5) C24 0.0169(6) 0.0189(7) 0.0286(7) -0.0004(5) 0.0022(5) -0.0002(5) C25 0.0193(7) 0.0220(8) 0.0598(11) -0.0032(7) 0.0071(7) -0.0027(6) C26 0.0147(6) 0.0229(7) 0.0264(7) -0.0022(5) 0.0003(5) -0.0018(5) C27 0.0177(7) 0.0299(9) 0.0457(9) -0.0035(7) 0.0057(6) 0.0066(6) C28 0.0161(6) 0.0167(7) 0.0240(7) -0.0025(5) 0.0019(5) 0.0005(5) C29 0.0193(6) 0.0198(7) 0.0220(7) 0.0007(5) 0.0007(5) -0.0002(5) C30 0.0234(7) 0.0170(7) 0.0293(7) 0.0003(5) 0.0019(5) -0.0008(5) C31 0.0260(7) 0.0217(8) 0.0289(7) -0.0055(6) -0.0015(6) -0.0022(6) C32 0.0342(8) 0.0279(8) 0.0229(7) -0.0010(6) -0.0048(6) -0.0005(6) C33 0.0269(7) 0.0210(7) 0.0263(7) 0.0024(6) -0.0020(5) 0.0006(6) C34 0.0683(13) 0.0207(9) 0.0494(11) -0.0097(8) -0.0103(9) -0.0052(8) C35 0.0187(6) 0.0185(7) 0.0254(7) 0.0003(5) 0.0015(5) 0.0013(5) C36 0.0198(7) 0.0237(8) 0.0315(8) 0.0053(6) -0.0006(5) 0.0013(6) C37 0.0217(7) 0.0401(10) 0.0455(10) 0.0154(8) 0.0063(6) 0.0044(7) C38 0.0166(6) 0.0182(7) 0.0252(7) 0.0002(5) -0.0017(5) 0.0020(5) C39 0.0259(8) 0.0221(8) 0.0434(9) -0.0029(6) -0.0005(6) -0.0064(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 O1 C26 1.2113(17) . ? O2 C26 1.3540(16) . ? O2 C27 1.4431(17) . ? O3 C38 1.2072(16) . ? O4 C38 1.3424(17) . ? O4 C39 1.4482(17) . ? O5 C31 1.3664(17) . ? O5 C34 1.432(2) . ? N1 C3 1.3952(16) . ? N1 N2 1.3960(16) . ? N1 C1 1.4643(16) . ? N2 C2 1.2914(17) . ? N3 C2 1.3951(17) . ? N3 C15 1.4396(16) . ? N3 C1 1.4820(17) . ? N4 C21 1.3954(17) . ? N4 C22 1.4263(17) . ? N4 C28 1.4343(17) . ? C1 C21 1.5346(19) . ? C1 C23 1.5845(18) . ? C2 C9 1.4689(18) . ? C3 C4 1.401(2) . ? C3 C8 1.4021(19) . ? C4 C5 1.3923(19) . ? C4 H4 0.9500 . ? C5 C6 1.383(2) . ? C5 H5 0.9500 . ? C6 C7 1.388(2) . ? C6 H6 0.9500 . ? C7 C8 1.3877(19) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.3945(19) . ? C9 C14 1.3986(18) . ? C10 C11 1.386(2) . ? C10 H10 0.9500 . ? C11 C12 1.387(2) . ? C11 H11 0.9500 . ? C12 C13 1.392(2) . ? C12 H12 0.9500 . ? C13 C14 1.385(2) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.3903(19) . ? C15 C20 1.3968(19) . ? C16 C17 1.388(2) . ? C16 H16 0.9500 . ? C17 C18 1.390(2) . ? C17 H17 0.9500 . ? C18 C19 1.383(2) . ? C18 H18 0.9500 . ? C19 C20 1.391(2) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C24 1.3576(18) . ? C22 C35 1.3362(18) . ? C22 C23 1.5009(18) . ? C23 C38 1.5159(18) . ? C23 H23 1.0000 . ? C24 C26 1.4819(19) . ? C24 C25 1.515(2) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 C29 1.3829(19) . ? C28 C33 1.3958(19) . ? C29 C30 1.3944(19) . ? C29 H29 0.9500 . ? C30 C31 1.392(2) . ? C30 H30 0.9500 . ? C31 C32 1.395(2) . ? C32 C33 1.383(2) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 C36 1.4997(19) . ? C35 H35 0.9500 . ? C36 C37 1.524(2) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? 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 C26 O2 C27 115.73(11) . . ? C38 O4 C39 115.49(11) . . ? C31 O5 C34 117.09(12) . . ? C3 N1 N2 118.88(10) . . ? C3 N1 C1 127.32(11) . . ? N2 N1 C1 112.33(10) . . ? C2 N2 N1 106.23(11) . . ? C2 N3 C15 122.43(11) . . ? C2 N3 C1 107.25(10) . . ? C15 N3 C1 123.00(11) . . ? C21 N4 C22 114.07(11) . . ? C21 N4 C28 123.43(11) . . ? C22 N4 C28 122.02(11) . . ? N1 C1 N3 99.89(10) . . ? N1 C1 C21 117.12(10) . . ? N3 C1 C21 114.65(11) . . ? N1 C1 C23 111.35(10) . . ? N3 C1 C23 111.61(10) . . ? C21 C1 C23 102.59(10) . . ? N2 C2 N3 114.21(12) . . ? N2 C2 C9 121.49(12) . . ? N3 C2 C9 124.05(11) . . ? N1 C3 C4 122.10(12) . . ? N1 C3 C8 119.07(12) . . ? C4 C3 C8 118.82(12) . . ? C5 C4 C3 119.95(13) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C6 C5 C4 121.16(14) . . ? C6 C5 H5 119.4 . . ? C4 C5 H5 119.4 . . ? C5 C6 C7 118.88(13) . . ? C5 C6 H6 120.6 . . ? C7 C6 H6 120.6 . . ? C6 C7 C8 121.05(14) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? C7 C8 C3 120.13(14) . . ? C7 C8 H8 119.9 . . ? C3 C8 H8 119.9 . . ? C10 C9 C14 119.24(13) . . ? C10 C9 C2 118.85(12) . . ? C14 C9 C2 121.88(12) . . ? C11 C10 C9 120.61(13) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 119.90(13) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C11 C12 C13 119.88(13) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C14 C13 C12 120.40(13) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C9 119.96(13) . . ? C13 C14 H14 120.0 . . ? C9 C14 H14 120.0 . . ? C16 C15 C20 119.78(12) . . ? C16 C15 N3 120.16(12) . . ? C20 C15 N3 119.94(12) . . ? C17 C16 C15 119.94(13) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 120.35(14) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C19 C18 C17 119.63(13) . . ? C19 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? C18 C19 C20 120.54(14) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C19 C20 C15 119.64(14) . . ? C19 C20 H20 120.2 . . ? C15 C20 H20 120.2 . . ? C24 C21 N4 125.22(12) . . ? C24 C21 C1 127.23(12) . . ? N4 C21 C1 106.90(11) . . ? C35 C22 N4 125.17(12) . . ? C35 C22 C23 127.99(12) . . ? N4 C22 C23 106.79(11) . . ? C22 C23 C38 117.06(11) . . ? C22 C23 C1 105.18(10) . . ? C38 C23 C1 109.22(11) . . ? C22 C23 H23 108.4 . . ? C38 C23 H23 108.4 . . ? C1 C23 H23 108.4 . . ? C21 C24 C26 119.84(12) . . ? C21 C24 C25 122.80(13) . . ? C26 C24 C25 117.13(12) . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O1 C26 O2 122.75(13) . . ? O1 C26 C24 126.75(12) . . ? O2 C26 C24 110.49(12) . . ? O2 C27 H27A 109.5 . . ? O2 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O2 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C29 C28 C33 119.62(12) . . ? C29 C28 N4 120.65(12) . . ? C33 C28 N4 119.73(12) . . ? C28 C29 C30 120.86(13) . . ? C28 C29 H29 119.6 . . ? C30 C29 H29 119.6 . . ? C31 C30 C29 119.39(13) . . ? C31 C30 H30 120.3 . . ? C29 C30 H30 120.3 . . ? O5 C31 C30 124.29(13) . . ? O5 C31 C32 115.99(13) . . ? C30 C31 C32 119.72(13) . . ? C33 C32 C31 120.55(13) . . ? C33 C32 H32 119.7 . . ? C31 C32 H32 119.7 . . ? C32 C33 C28 119.84(13) . . ? C32 C33 H33 120.1 . . ? C28 C33 H33 120.1 . . ? O5 C34 H34A 109.5 . . ? O5 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? O5 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C22 C35 C36 125.96(13) . . ? C22 C35 H35 117.0 . . ? C36 C35 H35 117.0 . . ? C35 C36 C37 112.15(13) . . ? C35 C36 H36A 109.2 . . ? C37 C36 H36A 109.2 . . ? C35 C36 H36B 109.2 . . ? C37 C36 H36B 109.2 . . ? H36A C36 H36B 107.9 . . ? C36 C37 H37A 109.5 . . ? C36 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C36 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? O3 C38 O4 123.59(12) . . ? O3 C38 C23 126.56(13) . . ? O4 C38 C23 109.80(11) . . ? O4 C39 H39A 109.5 . . ? O4 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? O4 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? 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 C3 N1 N2 C2 164.30(12) . . . . ? C1 N1 N2 C2 -2.88(14) . . . . ? C3 N1 C1 N3 -163.12(12) . . . . ? N2 N1 C1 N3 2.74(13) . . . . ? C3 N1 C1 C21 -38.73(18) . . . . ? N2 N1 C1 C21 127.13(12) . . . . ? C3 N1 C1 C23 78.87(16) . . . . ? N2 N1 C1 C23 -115.27(12) . . . . ? C2 N3 C1 N1 -1.62(13) . . . . ? C15 N3 C1 N1 148.97(11) . . . . ? C2 N3 C1 C21 -127.71(11) . . . . ? C15 N3 C1 C21 22.88(16) . . . . ? C2 N3 C1 C23 116.19(11) . . . . ? C15 N3 C1 C23 -93.22(14) . . . . ? N1 N2 C2 N3 1.72(15) . . . . ? N1 N2 C2 C9 176.19(12) . . . . ? C15 N3 C2 N2 -150.78(12) . . . . ? C1 N3 C2 N2 0.02(15) . . . . ? C15 N3 C2 C9 34.92(19) . . . . ? C1 N3 C2 C9 -174.29(12) . . . . ? N2 N1 C3 C4 175.25(12) . . . . ? C1 N1 C3 C4 -19.7(2) . . . . ? N2 N1 C3 C8 -4.05(18) . . . . ? C1 N1 C3 C8 160.99(13) . . . . ? N1 C3 C4 C5 179.69(13) . . . . ? C8 C3 C4 C5 -1.0(2) . . . . ? C3 C4 C5 C6 0.0(2) . . . . ? C4 C5 C6 C7 0.4(2) . . . . ? C5 C6 C7 C8 0.2(2) . . . . ? C6 C7 C8 C3 -1.2(2) . . . . ? N1 C3 C8 C7 -179.09(13) . . . . ? C4 C3 C8 C7 1.6(2) . . . . ? N2 C2 C9 C10 33.62(19) . . . . ? N3 C2 C9 C10 -152.47(13) . . . . ? N2 C2 C9 C14 -144.35(14) . . . . ? N3 C2 C9 C14 29.6(2) . . . . ? C14 C9 C10 C11 -0.8(2) . . . . ? C2 C9 C10 C11 -178.81(13) . . . . ? C9 C10 C11 C12 0.4(2) . . . . ? C10 C11 C12 C13 0.4(2) . . . . ? C11 C12 C13 C14 -0.8(2) . . . . ? C12 C13 C14 C9 0.4(2) . . . . ? C10 C9 C14 C13 0.4(2) . . . . ? C2 C9 C14 C13 178.35(13) . . . . ? C2 N3 C15 C16 32.16(18) . . . . ? C1 N3 C15 C16 -114.09(14) . . . . ? C2 N3 C15 C20 -144.06(13) . . . . ? C1 N3 C15 C20 69.68(17) . . . . ? C20 C15 C16 C17 3.6(2) . . . . ? N3 C15 C16 C17 -172.64(12) . . . . ? C15 C16 C17 C18 -1.9(2) . . . . ? C16 C17 C18 C19 -1.2(2) . . . . ? C17 C18 C19 C20 2.7(2) . . . . ? C18 C19 C20 C15 -1.1(2) . . . . ? C16 C15 C20 C19 -2.1(2) . . . . ? N3 C15 C20 C19 174.13(13) . . . . ? C22 N4 C21 C24 157.52(13) . . . . ? C28 N4 C21 C24 -30.2(2) . . . . ? C22 N4 C21 C1 -13.78(14) . . . . ? C28 N4 C21 C1 158.46(11) . . . . ? N1 C1 C21 C24 -28.58(19) . . . . ? N3 C1 C21 C24 87.98(16) . . . . ? C23 C1 C21 C24 -150.83(13) . . . . ? N1 C1 C21 N4 142.48(11) . . . . ? N3 C1 C21 N4 -100.95(12) . . . . ? C23 C1 C21 N4 20.23(13) . . . . ? C21 N4 C22 C35 -177.29(12) . . . . ? C28 N4 C22 C35 10.34(19) . . . . ? C21 N4 C22 C23 0.38(14) . . . . ? C28 N4 C22 C23 -171.99(11) . . . . ? C35 C22 C23 C38 -48.33(19) . . . . ? N4 C22 C23 C38 134.08(12) . . . . ? C35 C22 C23 C1 -169.77(13) . . . . ? N4 C22 C23 C1 12.64(13) . . . . ? N1 C1 C23 C22 -145.86(10) . . . . ? N3 C1 C23 C22 103.45(12) . . . . ? C21 C1 C23 C22 -19.79(12) . . . . ? N1 C1 C23 C38 87.71(13) . . . . ? N3 C1 C23 C38 -22.97(14) . . . . ? C21 C1 C23 C38 -146.21(10) . . . . ? N4 C21 C24 C26 175.48(12) . . . . ? C1 C21 C24 C26 -15.0(2) . . . . ? N4 C21 C24 C25 -10.2(2) . . . . ? C1 C21 C24 C25 159.32(14) . . . . ? C27 O2 C26 O1 2.5(2) . . . . ? C27 O2 C26 C24 -178.27(12) . . . . ? C21 C24 C26 O1 -36.1(2) . . . . ? C25 C24 C26 O1 149.23(15) . . . . ? C21 C24 C26 O2 144.65(13) . . . . ? C25 C24 C26 O2 -29.99(18) . . . . ? C21 N4 C28 C29 126.66(14) . . . . ? C22 N4 C28 C29 -61.69(17) . . . . ? C21 N4 C28 C33 -52.89(18) . . . . ? C22 N4 C28 C33 118.76(14) . . . . ? C33 C28 C29 C30 -0.7(2) . . . . ? N4 C28 C29 C30 179.78(12) . . . . ? C28 C29 C30 C31 1.1(2) . . . . ? C34 O5 C31 C30 -1.3(2) . . . . ? C34 O5 C31 C32 179.32(15) . . . . ? C29 C30 C31 O5 -179.95(13) . . . . ? C29 C30 C31 C32 -0.6(2) . . . . ? O5 C31 C32 C33 178.97(14) . . . . ? C30 C31 C32 C33 -0.4(2) . . . . ? C31 C32 C33 C28 0.9(2) . . . . ? C29 C28 C33 C32 -0.4(2) . . . . ? N4 C28 C33 C32 179.18(12) . . . . ? N4 C22 C35 C36 176.24(12) . . . . ? C23 C22 C35 C36 -0.9(2) . . . . ? C22 C35 C36 C37 120.62(16) . . . . ? C39 O4 C38 O3 -5.18(19) . . . . ? C39 O4 C38 C23 172.38(11) . . . . ? C22 C23 C38 O3 -18.0(2) . . . . ? C1 C23 C38 O3 101.29(15) . . . . ? C22 C23 C38 O4 164.51(11) . . . . ? C1 C23 C38 O4 -76.19(13) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.246 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.052 # Attachment '20b.cif' data_20b _database_code_depnum_ccdc_archive 'CCDC 740322' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; (R,E)-methyl 6-(1-methoxy-1-oxopropan-2-ylidene)-7-(4- methoxyphenyl)-1,3,4-triphenyl-8-propyl-1,2,4,7-tetraazaspiro(4.4)nona- 2,8-diene-9-carboxylate ; _chemical_melting_point ? _chemical_formula_moiety 'C39 H38 N4 O5' _chemical_formula_sum 'C39 H38 N4 O5' _chemical_formula_weight 642.73 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 21/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.2415(9) _cell_length_b 20.801(2) _cell_length_c 17.0490(16) _cell_angle_alpha 90.00 _cell_angle_beta 92.631(4) _cell_angle_gamma 90.00 _cell_volume 3273.9(6) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 6935 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 27.9 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9828 _exptl_absorpt_correction_T_max 0.9879 _exptl_absorpt_process_details CrystalClear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 40544 _diffrn_reflns_av_R_equivalents 0.0512 _diffrn_reflns_av_sigmaI/netI 0.0379 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 27.87 _reflns_number_total 7773 _reflns_number_gt 6388 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear(Rigaku/MSC Inc., 2005)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CrystalStructure 3.7.0' _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^)+(0.0533P)^2^+0.9754P] 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 SHELXL _refine_ls_extinction_coef 0.0091(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7773 _refine_ls_number_parameters 440 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0596 _refine_ls_R_factor_gt 0.0466 _refine_ls_wR_factor_ref 0.1180 _refine_ls_wR_factor_gt 0.1108 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 O1 O -0.14221(12) 0.17273(4) 0.00356(6) 0.0279(2) Uani 1 1 d . . . O2 O -0.28645(11) 0.23701(5) -0.07161(6) 0.0270(2) Uani 1 1 d . . . O3 O -0.19365(12) 0.50866(5) 0.29703(6) 0.0330(3) Uani 1 1 d . . . O4 O 0.37124(11) 0.28564(5) -0.11421(6) 0.0256(2) Uani 1 1 d . . . O5 O 0.43372(11) 0.38278(4) -0.06468(6) 0.0262(2) Uani 1 1 d . . . N1 N 0.03791(13) 0.26487(5) -0.10755(6) 0.0204(2) Uani 1 1 d . . . N2 N 0.16164(12) 0.22034(5) -0.00604(6) 0.0190(2) Uani 1 1 d . . . N3 N 0.08036(13) 0.20284(5) -0.13069(6) 0.0207(2) Uani 1 1 d . . . N4 N 0.04818(12) 0.36667(5) 0.05850(6) 0.0197(2) Uani 1 1 d . . . C1 C 0.10163(15) 0.28361(6) -0.03062(7) 0.0186(3) Uani 1 1 d . . . C2 C 0.15036(15) 0.17920(6) -0.07002(7) 0.0200(3) Uani 1 1 d . . . C3 C -0.02499(14) 0.30663(6) -0.16278(7) 0.0186(3) Uani 1 1 d . . . C4 C -0.05514(15) 0.37090(6) -0.14466(8) 0.0219(3) Uani 1 1 d . . . H4 H -0.0315 0.3871 -0.0936 0.026 Uiso 1 1 calc R . . C5 C -0.11960(15) 0.41098(6) -0.20141(8) 0.0244(3) Uani 1 1 d . . . H5 H -0.1400 0.4543 -0.1883 0.029 Uiso 1 1 calc R . . C6 C -0.15461(17) 0.38910(7) -0.27632(9) 0.0304(3) Uani 1 1 d . . . H6 H -0.1971 0.4171 -0.3149 0.037 Uiso 1 1 calc R . . C7 C -0.12637(18) 0.32536(8) -0.29406(9) 0.0339(4) Uani 1 1 d . . . H7 H -0.1500 0.3097 -0.3454 0.041 Uiso 1 1 calc R . . C8 C -0.06434(16) 0.28420(7) -0.23816(8) 0.0266(3) Uani 1 1 d . . . H8 H -0.0484 0.2404 -0.2511 0.032 Uiso 1 1 calc R . . C9 C 0.26326(15) 0.21509(6) 0.05905(7) 0.0196(3) Uani 1 1 d . . . C10 C 0.22129(17) 0.23365(6) 0.13312(8) 0.0249(3) Uani 1 1 d . . . H10 H 0.1253 0.2484 0.1397 0.030 Uiso 1 1 calc R . . C11 C 0.31893(18) 0.23076(7) 0.19754(8) 0.0290(3) Uani 1 1 d . . . H11 H 0.2906 0.2448 0.2476 0.035 Uiso 1 1 calc R . . C12 C 0.45751(18) 0.20741(7) 0.18870(9) 0.0303(3) Uani 1 1 d . . . H12 H 0.5243 0.2051 0.2327 0.036 Uiso 1 1 calc R . . C13 C 0.49841(16) 0.18734(7) 0.11508(9) 0.0279(3) Uani 1 1 d . . . H13 H 0.5924 0.1700 0.1093 0.033 Uiso 1 1 calc R . . C14 C 0.40296(16) 0.19239(6) 0.05002(8) 0.0235(3) Uani 1 1 d . . . H14 H 0.4331 0.1804 -0.0005 0.028 Uiso 1 1 calc R . . C15 C 0.20446(15) 0.11251(6) -0.06554(8) 0.0222(3) Uani 1 1 d . . . C16 C 0.16229(18) 0.07250(7) -0.00501(9) 0.0301(3) Uani 1 1 d . . . H16 H 0.0962 0.0877 0.0318 0.036 Uiso 1 1 calc R . . C17 C 0.2170(2) 0.01038(7) 0.00141(10) 0.0382(4) Uani 1 1 d . . . H17 H 0.1871 -0.0171 0.0422 0.046 Uiso 1 1 calc R . . C18 C 0.3144(2) -0.01143(7) -0.05130(10) 0.0398(4) Uani 1 1 d . . . H18 H 0.3534 -0.0536 -0.0460 0.048 Uiso 1 1 calc R . . C19 C 0.3558(2) 0.02791(7) -0.11201(9) 0.0369(4) Uani 1 1 d . . . H19 H 0.4224 0.0125 -0.1485 0.044 Uiso 1 1 calc R . . C20 C 0.29992(17) 0.08987(7) -0.11961(9) 0.0289(3) Uani 1 1 d . . . H20 H 0.3271 0.1166 -0.1617 0.035 Uiso 1 1 calc R . . C21 C -0.01334(15) 0.31080(6) 0.02332(7) 0.0187(3) Uani 1 1 d . . . C22 C -0.14720(15) 0.28721(6) 0.02924(7) 0.0202(3) Uani 1 1 d . . . C23 C -0.26917(16) 0.31554(7) 0.07411(9) 0.0269(3) Uani 1 1 d . . . H23A H -0.2504 0.3083 0.1305 0.040 Uiso 1 1 calc R . . H23B H -0.3607 0.2949 0.0572 0.040 Uiso 1 1 calc R . . H23C H -0.2756 0.3618 0.0638 0.040 Uiso 1 1 calc R . . C24 C -0.18594(15) 0.22570(6) -0.01378(8) 0.0206(3) Uani 1 1 d . . . C25 C -0.33179(18) 0.18200(7) -0.11822(9) 0.0332(4) Uani 1 1 d . . . H25A H -0.2516 0.1677 -0.1496 0.050 Uiso 1 1 calc R . . H25B H -0.4145 0.1939 -0.1532 0.050 Uiso 1 1 calc R . . H25C H -0.3600 0.1471 -0.0835 0.050 Uiso 1 1 calc R . . C26 C -0.01436(15) 0.40455(6) 0.11875(7) 0.0191(3) Uani 1 1 d . . . C27 C -0.09724(15) 0.45821(6) 0.09892(8) 0.0211(3) Uani 1 1 d . . . H27 H -0.1115 0.4702 0.0453 0.025 Uiso 1 1 calc R . . C28 C -0.15966(15) 0.49471(6) 0.15684(8) 0.0230(3) Uani 1 1 d . . . H28 H -0.2165 0.5314 0.1430 0.028 Uiso 1 1 calc R . . C29 C -0.13798(15) 0.47695(6) 0.23536(8) 0.0233(3) Uani 1 1 d . . . C30 C -0.05369(16) 0.42335(6) 0.25536(8) 0.0236(3) Uani 1 1 d . . . H30 H -0.0387 0.4114 0.3089 0.028 Uiso 1 1 calc R . . C31 C 0.00811(15) 0.38755(6) 0.19739(8) 0.0216(3) Uani 1 1 d . . . H31 H 0.0661 0.3512 0.2112 0.026 Uiso 1 1 calc R . . C32 C -0.26021(19) 0.56961(7) 0.28208(10) 0.0352(4) Uani 1 1 d . . . H32A H -0.1916 0.5981 0.2571 0.053 Uiso 1 1 calc R . . H32B H -0.2884 0.5886 0.3317 0.053 Uiso 1 1 calc R . . H32C H -0.3464 0.5639 0.2471 0.053 Uiso 1 1 calc R . . C33 C 0.21641(15) 0.33604(6) -0.02696(7) 0.0191(3) Uani 1 1 d . . . C34 C 0.18293(14) 0.37957(6) 0.02894(7) 0.0191(3) Uani 1 1 d . . . C35 C 0.27440(15) 0.43156(6) 0.06619(8) 0.0217(3) Uani 1 1 d . . . H35A H 0.2116 0.4646 0.0889 0.026 Uiso 1 1 calc R . . H35B H 0.3326 0.4524 0.0261 0.026 Uiso 1 1 calc R . . C36 C 0.37561(16) 0.40248(7) 0.13122(9) 0.0281(3) Uani 1 1 d . . . H36A H 0.3165 0.3807 0.1703 0.034 Uiso 1 1 calc R . . H36B H 0.4383 0.3697 0.1079 0.034 Uiso 1 1 calc R . . C37 C 0.46998(19) 0.45287(8) 0.17239(10) 0.0390(4) Uani 1 1 d . . . H37A H 0.5293 0.4743 0.1340 0.058 Uiso 1 1 calc R . . H37B H 0.5332 0.4322 0.2127 0.058 Uiso 1 1 calc R . . H37C H 0.4085 0.4847 0.1971 0.058 Uiso 1 1 calc R . . C38 C 0.34502(15) 0.33086(6) -0.07246(7) 0.0198(3) Uani 1 1 d . . . C39 C 0.56428(16) 0.37992(7) -0.10801(9) 0.0276(3) Uani 1 1 d . . . H39A H 0.6130 0.3387 -0.0978 0.041 Uiso 1 1 calc R . . H39B H 0.6290 0.4152 -0.0913 0.041 Uiso 1 1 calc R . . H39C H 0.5394 0.3840 -0.1643 0.041 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0334(6) 0.0192(5) 0.0309(5) 0.0010(4) -0.0012(4) -0.0007(4) O2 0.0256(5) 0.0239(5) 0.0306(5) -0.0043(4) -0.0068(4) -0.0010(4) O3 0.0415(7) 0.0306(5) 0.0275(5) -0.0053(4) 0.0074(5) 0.0120(5) O4 0.0285(6) 0.0253(5) 0.0233(5) -0.0047(4) 0.0048(4) -0.0001(4) O5 0.0240(5) 0.0226(5) 0.0326(5) -0.0031(4) 0.0091(4) -0.0046(4) N1 0.0265(6) 0.0162(5) 0.0181(5) -0.0032(4) -0.0027(4) 0.0027(4) N2 0.0226(6) 0.0157(5) 0.0185(5) -0.0010(4) -0.0010(4) 0.0021(4) N3 0.0246(6) 0.0161(5) 0.0215(5) -0.0039(4) 0.0004(5) 0.0014(4) N4 0.0198(6) 0.0182(5) 0.0212(5) -0.0043(4) 0.0024(4) -0.0014(4) C1 0.0220(7) 0.0160(6) 0.0178(6) -0.0005(4) -0.0005(5) -0.0004(5) C2 0.0215(7) 0.0182(6) 0.0203(6) -0.0020(5) 0.0017(5) -0.0010(5) C3 0.0167(6) 0.0208(6) 0.0184(6) 0.0007(5) 0.0010(5) -0.0002(5) C4 0.0233(7) 0.0209(6) 0.0212(6) -0.0012(5) -0.0001(5) -0.0007(5) C5 0.0228(7) 0.0219(6) 0.0286(7) 0.0018(5) 0.0009(6) 0.0023(5) C6 0.0311(8) 0.0317(7) 0.0278(7) 0.0044(6) -0.0064(6) 0.0067(6) C7 0.0402(9) 0.0387(8) 0.0220(7) -0.0042(6) -0.0085(6) 0.0085(7) C8 0.0293(8) 0.0265(7) 0.0233(7) -0.0049(5) -0.0039(6) 0.0061(6) C9 0.0242(7) 0.0154(5) 0.0190(6) 0.0011(4) -0.0018(5) -0.0023(5) C10 0.0313(8) 0.0221(6) 0.0212(6) 0.0010(5) 0.0009(6) 0.0034(6) C11 0.0428(9) 0.0241(7) 0.0199(6) 0.0014(5) -0.0025(6) -0.0010(6) C12 0.0370(9) 0.0261(7) 0.0267(7) 0.0061(6) -0.0104(6) -0.0067(6) C13 0.0234(8) 0.0254(7) 0.0345(8) 0.0046(6) -0.0038(6) -0.0026(6) C14 0.0247(7) 0.0223(6) 0.0235(6) 0.0002(5) 0.0011(5) -0.0022(5) C15 0.0258(7) 0.0172(6) 0.0232(6) -0.0030(5) -0.0041(5) 0.0007(5) C16 0.0365(9) 0.0230(7) 0.0308(7) 0.0004(6) 0.0020(6) 0.0004(6) C17 0.0551(11) 0.0224(7) 0.0365(8) 0.0045(6) -0.0028(8) -0.0007(7) C18 0.0593(12) 0.0220(7) 0.0368(9) -0.0055(6) -0.0122(8) 0.0109(7) C19 0.0474(10) 0.0304(8) 0.0324(8) -0.0103(6) -0.0021(7) 0.0137(7) C20 0.0360(9) 0.0256(7) 0.0250(7) -0.0038(5) -0.0001(6) 0.0038(6) C21 0.0234(7) 0.0151(5) 0.0173(6) -0.0006(4) 0.0000(5) 0.0005(5) C22 0.0231(7) 0.0186(6) 0.0189(6) -0.0006(5) 0.0015(5) -0.0006(5) C23 0.0231(8) 0.0267(7) 0.0312(7) -0.0069(6) 0.0059(6) -0.0027(6) C24 0.0192(7) 0.0214(6) 0.0214(6) -0.0012(5) 0.0027(5) -0.0023(5) C25 0.0317(9) 0.0328(8) 0.0344(8) -0.0124(6) -0.0048(6) -0.0052(6) C26 0.0195(7) 0.0168(6) 0.0210(6) -0.0035(5) 0.0025(5) -0.0019(5) C27 0.0226(7) 0.0196(6) 0.0211(6) 0.0004(5) 0.0001(5) -0.0007(5) C28 0.0222(7) 0.0182(6) 0.0286(7) -0.0003(5) -0.0002(5) 0.0023(5) C29 0.0239(7) 0.0230(6) 0.0233(6) -0.0048(5) 0.0054(5) -0.0011(5) C30 0.0270(7) 0.0232(6) 0.0206(6) -0.0004(5) 0.0018(5) -0.0003(5) C31 0.0232(7) 0.0183(6) 0.0234(6) 0.0000(5) 0.0008(5) 0.0000(5) C32 0.0382(9) 0.0296(7) 0.0380(8) -0.0090(6) 0.0038(7) 0.0122(7) C33 0.0213(7) 0.0173(6) 0.0187(6) 0.0007(5) 0.0001(5) 0.0002(5) C34 0.0199(7) 0.0177(6) 0.0195(6) 0.0019(5) 0.0004(5) -0.0004(5) C35 0.0221(7) 0.0185(6) 0.0244(6) -0.0032(5) 0.0022(5) -0.0029(5) C36 0.0256(8) 0.0278(7) 0.0305(7) -0.0019(6) -0.0027(6) -0.0019(6) C37 0.0334(9) 0.0396(9) 0.0427(9) -0.0039(7) -0.0105(7) -0.0074(7) C38 0.0221(7) 0.0192(6) 0.0179(6) 0.0022(5) -0.0005(5) -0.0002(5) C39 0.0230(8) 0.0274(7) 0.0331(7) 0.0012(6) 0.0087(6) -0.0009(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 O1 C24 1.2057(16) . ? O2 C24 1.3440(16) . ? O2 C25 1.4441(16) . ? O3 C29 1.3619(16) . ? O3 C32 1.4270(18) . ? O4 C38 1.2109(16) . ? O5 C38 1.3587(16) . ? O5 C39 1.4446(17) . ? N1 C3 1.3889(16) . ? N1 N3 1.4102(14) . ? N1 C1 1.4656(16) . ? N2 C2 1.3865(16) . ? N2 C9 1.4246(16) . ? N2 C1 1.4812(15) . ? N3 C2 1.2918(17) . ? N4 C34 1.3908(17) . ? N4 C21 1.4151(15) . ? N4 C26 1.4369(16) . ? C1 C33 1.5206(18) . ? C1 C21 1.5440(19) . ? C2 C15 1.4753(17) . ? C3 C8 1.3995(18) . ? C3 C4 1.4029(17) . ? C4 C5 1.3903(18) . ? C4 H4 0.9500 . ? C5 C6 1.380(2) . ? C5 H5 0.9500 . ? C6 C7 1.387(2) . ? C6 H6 0.9500 . ? C7 C8 1.386(2) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C14 1.390(2) . ? C9 C10 1.3925(18) . ? C10 C11 1.3904(19) . ? C10 H10 0.9500 . ? C11 C12 1.384(2) . ? C11 H11 0.9500 . ? C12 C13 1.391(2) . ? C12 H12 0.9500 . ? C13 C14 1.3891(19) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C20 1.387(2) . ? C15 C16 1.395(2) . ? C16 C17 1.390(2) . ? C16 H16 0.9500 . ? C17 C18 1.378(3) . ? C17 H17 0.9500 . ? C18 C19 1.387(2) . ? C18 H18 0.9500 . ? C19 C20 1.392(2) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C22 1.3389(19) . ? C22 C24 1.5096(17) . ? C22 C23 1.5106(19) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 C27 1.3868(18) . ? C26 C31 1.3929(18) . ? C27 C28 1.3915(19) . ? C27 H27 0.9500 . ? C28 C29 1.3943(19) . ? C28 H28 0.9500 . ? C29 C30 1.3935(19) . ? C30 C31 1.3818(19) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 C34 1.3604(18) . ? C33 C38 1.4528(19) . ? C34 C35 1.4961(17) . ? C35 C36 1.5411(19) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 C37 1.515(2) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? 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 C24 O2 C25 116.00(11) . . ? C29 O3 C32 117.86(11) . . ? C38 O5 C39 115.57(10) . . ? C3 N1 N3 119.71(10) . . ? C3 N1 C1 125.37(10) . . ? N3 N1 C1 112.84(10) . . ? C2 N2 C9 126.05(11) . . ? C2 N2 C1 108.19(10) . . ? C9 N2 C1 120.88(10) . . ? C2 N3 N1 105.06(10) . . ? C34 N4 C21 110.72(10) . . ? C34 N4 C26 123.34(10) . . ? C21 N4 C26 125.90(11) . . ? N1 C1 N2 98.44(9) . . ? N1 C1 C33 118.58(11) . . ? N2 C1 C33 111.98(11) . . ? N1 C1 C21 111.79(11) . . ? N2 C1 C21 114.58(10) . . ? C33 C1 C21 102.16(10) . . ? N3 C2 N2 114.32(11) . . ? N3 C2 C15 123.74(11) . . ? N2 C2 C15 121.77(11) . . ? N1 C3 C8 119.81(12) . . ? N1 C3 C4 121.86(11) . . ? C8 C3 C4 118.30(12) . . ? C5 C4 C3 120.08(12) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C6 C5 C4 121.40(13) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C7 118.58(13) . . ? C5 C6 H6 120.7 . . ? C7 C6 H6 120.7 . . ? C8 C7 C6 121.11(13) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C7 C8 C3 120.50(13) . . ? C7 C8 H8 119.8 . . ? C3 C8 H8 119.8 . . ? C14 C9 C10 119.56(12) . . ? C14 C9 N2 121.49(12) . . ? C10 C9 N2 118.95(12) . . ? C11 C10 C9 120.45(14) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C12 C11 C10 119.95(14) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C13 119.63(13) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C14 C13 C12 120.58(14) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C9 119.76(13) . . ? C13 C14 H14 120.1 . . ? C9 C14 H14 120.1 . . ? C20 C15 C16 119.79(13) . . ? C20 C15 C2 120.61(12) . . ? C16 C15 C2 119.58(13) . . ? C17 C16 C15 120.00(15) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C18 C17 C16 120.05(15) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C17 C18 C19 120.22(14) . . ? C17 C18 H18 119.9 . . ? C19 C18 H18 119.9 . . ? C18 C19 C20 120.13(15) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C15 C20 C19 119.79(14) . . ? C15 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C22 C21 N4 128.58(12) . . ? C22 C21 C1 125.04(11) . . ? N4 C21 C1 106.21(11) . . ? C21 C22 C24 118.25(12) . . ? C21 C22 C23 127.50(12) . . ? C24 C22 C23 114.25(11) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O1 C24 O2 123.53(12) . . ? O1 C24 C22 125.88(12) . . ? O2 C24 C22 110.40(11) . . ? O2 C25 H25A 109.5 . . ? O2 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O2 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C27 C26 C31 119.69(12) . . ? C27 C26 N4 120.19(11) . . ? C31 C26 N4 120.13(11) . . ? C26 C27 C28 120.56(12) . . ? C26 C27 H27 119.7 . . ? C28 C27 H27 119.7 . . ? C27 C28 C29 119.40(12) . . ? C27 C28 H28 120.3 . . ? C29 C28 H28 120.3 . . ? O3 C29 C30 115.16(12) . . ? O3 C29 C28 124.77(13) . . ? C30 C29 C28 120.07(12) . . ? C31 C30 C29 120.06(12) . . ? C31 C30 H30 120.0 . . ? C29 C30 H30 120.0 . . ? C30 C31 C26 120.23(12) . . ? C30 C31 H31 119.9 . . ? C26 C31 H31 119.9 . . ? O3 C32 H32A 109.5 . . ? O3 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? O3 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C34 C33 C38 129.89(12) . . ? C34 C33 C1 108.99(11) . . ? C38 C33 C1 120.74(11) . . ? C33 C34 N4 111.20(11) . . ? C33 C34 C35 129.52(12) . . ? N4 C34 C35 118.91(11) . . ? C34 C35 C36 109.52(11) . . ? C34 C35 H35A 109.8 . . ? C36 C35 H35A 109.8 . . ? C34 C35 H35B 109.8 . . ? C36 C35 H35B 109.8 . . ? H35A C35 H35B 108.2 . . ? C37 C36 C35 112.28(12) . . ? C37 C36 H36A 109.1 . . ? C35 C36 H36A 109.1 . . ? C37 C36 H36B 109.1 . . ? C35 C36 H36B 109.1 . . ? H36A C36 H36B 107.9 . . ? C36 C37 H37A 109.5 . . ? C36 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C36 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? O4 C38 O5 122.60(12) . . ? O4 C38 C33 124.20(12) . . ? O5 C38 C33 113.19(11) . . ? O5 C39 H39A 109.5 . . ? O5 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? O5 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? 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 C3 N1 N3 C2 172.16(12) . . . . ? C1 N1 N3 C2 7.64(15) . . . . ? C3 N1 C1 N2 -174.05(12) . . . . ? N3 N1 C1 N2 -10.57(13) . . . . ? C3 N1 C1 C33 -53.28(18) . . . . ? N3 N1 C1 C33 110.20(13) . . . . ? C3 N1 C1 C21 65.15(16) . . . . ? N3 N1 C1 C21 -131.37(11) . . . . ? C2 N2 C1 N1 9.62(13) . . . . ? C9 N2 C1 N1 166.31(11) . . . . ? C2 N2 C1 C33 -115.93(12) . . . . ? C9 N2 C1 C33 40.76(16) . . . . ? C2 N2 C1 C21 128.33(12) . . . . ? C9 N2 C1 C21 -74.98(15) . . . . ? N1 N3 C2 N2 -0.64(15) . . . . ? N1 N3 C2 C15 174.64(12) . . . . ? C9 N2 C2 N3 -161.45(12) . . . . ? C1 N2 C2 N3 -6.29(16) . . . . ? C9 N2 C2 C15 23.2(2) . . . . ? C1 N2 C2 C15 178.32(12) . . . . ? N3 N1 C3 C8 8.90(19) . . . . ? C1 N1 C3 C8 171.34(13) . . . . ? N3 N1 C3 C4 -173.21(12) . . . . ? C1 N1 C3 C4 -10.8(2) . . . . ? N1 C3 C4 C5 -179.32(13) . . . . ? C8 C3 C4 C5 -1.4(2) . . . . ? C3 C4 C5 C6 -0.3(2) . . . . ? C4 C5 C6 C7 1.1(2) . . . . ? C5 C6 C7 C8 0.0(3) . . . . ? C6 C7 C8 C3 -1.8(3) . . . . ? N1 C3 C8 C7 -179.60(14) . . . . ? C4 C3 C8 C7 2.4(2) . . . . ? C2 N2 C9 C14 34.61(19) . . . . ? C1 N2 C9 C14 -117.69(14) . . . . ? C2 N2 C9 C10 -145.87(13) . . . . ? C1 N2 C9 C10 61.84(16) . . . . ? C14 C9 C10 C11 1.2(2) . . . . ? N2 C9 C10 C11 -178.28(12) . . . . ? C9 C10 C11 C12 -2.0(2) . . . . ? C10 C11 C12 C13 0.4(2) . . . . ? C11 C12 C13 C14 2.0(2) . . . . ? C12 C13 C14 C9 -2.8(2) . . . . ? C10 C9 C14 C13 1.16(19) . . . . ? N2 C9 C14 C13 -179.32(12) . . . . ? N3 C2 C15 C20 58.4(2) . . . . ? N2 C2 C15 C20 -126.68(15) . . . . ? N3 C2 C15 C16 -123.44(15) . . . . ? N2 C2 C15 C16 51.50(19) . . . . ? C20 C15 C16 C17 0.6(2) . . . . ? C2 C15 C16 C17 -177.59(14) . . . . ? C15 C16 C17 C18 0.9(2) . . . . ? C16 C17 C18 C19 -1.5(3) . . . . ? C17 C18 C19 C20 0.5(3) . . . . ? C16 C15 C20 C19 -1.6(2) . . . . ? C2 C15 C20 C19 176.60(13) . . . . ? C18 C19 C20 C15 1.0(2) . . . . ? C34 N4 C21 C22 -171.48(13) . . . . ? C26 N4 C21 C22 10.8(2) . . . . ? C34 N4 C21 C1 3.93(13) . . . . ? C26 N4 C21 C1 -173.82(11) . . . . ? N1 C1 C21 C22 40.55(17) . . . . ? N2 C1 C21 C22 -70.34(16) . . . . ? C33 C1 C21 C22 168.36(12) . . . . ? N1 C1 C21 N4 -135.07(10) . . . . ? N2 C1 C21 N4 114.04(11) . . . . ? C33 C1 C21 N4 -7.25(12) . . . . ? N4 C21 C22 C24 -179.25(12) . . . . ? C1 C21 C22 C24 6.14(19) . . . . ? N4 C21 C22 C23 1.6(2) . . . . ? C1 C21 C22 C23 -173.05(12) . . . . ? C25 O2 C24 O1 -5.6(2) . . . . ? C25 O2 C24 C22 179.19(12) . . . . ? C21 C22 C24 O1 71.67(18) . . . . ? C23 C22 C24 O1 -109.04(16) . . . . ? C21 C22 C24 O2 -113.21(14) . . . . ? C23 C22 C24 O2 66.08(15) . . . . ? C34 N4 C26 C27 87.92(16) . . . . ? C21 N4 C26 C27 -94.60(15) . . . . ? C34 N4 C26 C31 -92.02(16) . . . . ? C21 N4 C26 C31 85.46(16) . . . . ? C31 C26 C27 C28 -0.8(2) . . . . ? N4 C26 C27 C28 179.22(12) . . . . ? C26 C27 C28 C29 0.1(2) . . . . ? C32 O3 C29 C30 169.75(13) . . . . ? C32 O3 C29 C28 -10.0(2) . . . . ? C27 C28 C29 O3 -179.80(13) . . . . ? C27 C28 C29 C30 0.4(2) . . . . ? O3 C29 C30 C31 179.95(12) . . . . ? C28 C29 C30 C31 -0.2(2) . . . . ? C29 C30 C31 C26 -0.5(2) . . . . ? C27 C26 C31 C30 1.0(2) . . . . ? N4 C26 C31 C30 -179.04(12) . . . . ? N1 C1 C33 C34 131.78(12) . . . . ? N2 C1 C33 C34 -114.65(12) . . . . ? C21 C1 C33 C34 8.43(13) . . . . ? N1 C1 C33 C38 -54.61(16) . . . . ? N2 C1 C33 C38 58.97(15) . . . . ? C21 C1 C33 C38 -177.96(11) . . . . ? C38 C33 C34 N4 -179.48(12) . . . . ? C1 C33 C34 N4 -6.63(15) . . . . ? C38 C33 C34 C35 -6.7(2) . . . . ? C1 C33 C34 C35 166.16(12) . . . . ? C21 N4 C34 C33 1.64(15) . . . . ? C26 N4 C34 C33 179.46(11) . . . . ? C21 N4 C34 C35 -172.01(11) . . . . ? C26 N4 C34 C35 5.81(18) . . . . ? C33 C34 C35 C36 -80.51(17) . . . . ? N4 C34 C35 C36 91.81(14) . . . . ? C34 C35 C36 C37 -179.10(13) . . . . ? C39 O5 C38 O4 -1.60(18) . . . . ? C39 O5 C38 C33 179.34(11) . . . . ? C34 C33 C38 O4 170.81(13) . . . . ? C1 C33 C38 O4 -1.31(19) . . . . ? C34 C33 C38 O5 -10.14(19) . . . . ? C1 C33 C38 O5 177.74(11) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.282 _refine_diff_density_min -0.242 _refine_diff_density_rms 0.051