# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'RSC Advances' _journal_coden_cambridge 1500 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Jianlin Han' _publ_contact_author_email hanjl@nju.edu.cn _publ_author_name 'Jianlin Han' # Attachment '- 6j.cif' data_2011122m _database_code_depnum_ccdc_archive 'CCDC 861353' #TrackingRef '- 6j.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H24 Cl N3 O5' _chemical_formula_sum 'C23 H24 Cl N3 O5' _chemical_formula_weight 457.90 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 9.3812(14) _cell_length_b 19.472(3) _cell_length_c 13.1900(19) _cell_angle_alpha 90.00 _cell_angle_beta 106.254(2) _cell_angle_gamma 90.00 _cell_volume 2313.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960.0 _exptl_absorpt_coefficient_mu 0.204 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.943 _exptl_absorpt_correction_T_max 0.954 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Apex II CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15963 _diffrn_reflns_av_R_equivalents 0.0982 _diffrn_reflns_av_sigmaI/netI 0.0718 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 28.28 _reflns_number_total 5737 _reflns_number_gt 4202 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SHELXTL Program' _computing_data_reduction Saint _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL Program' _computing_publication_material 'Bruker SHELXTL Program' _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^)+(0.1102P)^2^+0.0189P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5737 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0769 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.1876 _refine_ls_wR_factor_gt 0.1728 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 Cl1 Cl 0.74846(9) 0.02488(4) -0.06195(4) 0.0849(2) Uani 1 1 d . . . O5 O 1.09262(12) 0.05685(6) 0.39610(9) 0.0476(3) Uani 1 1 d . . . N2 N 1.02618(14) 0.16419(7) 0.41922(10) 0.0420(3) Uani 1 1 d . . . O4 O 1.26780(13) 0.13224(7) 0.48004(11) 0.0617(4) Uani 1 1 d . . . N1 N 0.88151(14) 0.14594(7) 0.36316(10) 0.0412(3) Uani 1 1 d . . . O1 O 0.64939(14) 0.18836(8) 0.35353(11) 0.0629(4) Uani 1 1 d . . . C19 C 1.14360(17) 0.11637(9) 0.43681(12) 0.0424(3) Uani 1 1 d . . . C4 C 0.85057(16) 0.11883(8) 0.25924(11) 0.0383(3) Uani 1 1 d . . . C7 C 0.78262(18) 0.18853(9) 0.39462(12) 0.0457(4) Uani 1 1 d . . . C8 C 1.01678(18) 0.21443(8) 0.49280(12) 0.0432(3) Uani 1 1 d . . . C3 C 0.93769(19) 0.13462(9) 0.19483(13) 0.0485(4) Uani 1 1 d . . . H3 H 1.0175 0.1645 0.2178 0.058 Uiso 1 1 calc R . . C15 C 0.74433(18) 0.25301(10) 0.61944(14) 0.0511(4) Uani 1 1 d . . . C5 C 0.72833(19) 0.07649(9) 0.22438(12) 0.0481(4) Uani 1 1 d . . . H5 H 0.6686 0.0669 0.2682 0.058 Uiso 1 1 calc R . . C6 C 0.6952(2) 0.04863(10) 0.12464(14) 0.0536(4) Uani 1 1 d . . . H6 H 0.6123 0.0207 0.1001 0.064 Uiso 1 1 calc R . . C1 C 0.7859(2) 0.06255(10) 0.06218(12) 0.0535(4) Uani 1 1 d . . . C9 C 0.87313(18) 0.22998(8) 0.47927(13) 0.0460(4) Uani 1 1 d . . . C20 C 1.1972(2) 0.00079(10) 0.38820(16) 0.0576(5) Uani 1 1 d . . . C14 C 0.6172(2) 0.21345(11) 0.59146(15) 0.0571(5) Uani 1 1 d . . . H14 H 0.5676 0.2067 0.5205 0.069 Uiso 1 1 calc R . . C17 C 0.8145(2) 0.28370(10) 0.53862(15) 0.0550(4) Uani 1 1 d . . . H17 H 0.8996 0.3111 0.5779 0.066 Uiso 1 1 calc R . . C13 C 0.5634(2) 0.18392(11) 0.66823(18) 0.0640(5) Uani 1 1 d . . . H13 H 0.4771 0.1578 0.6486 0.077 Uiso 1 1 calc R . . N3 N 0.7885(3) 0.36432(11) 0.3906(2) 0.0850(6) Uani 1 1 d . . . C2 C 0.9057(2) 0.10565(11) 0.09537(14) 0.0571(5) Uani 1 1 d . . . H2 H 0.9650 0.1153 0.0512 0.069 Uiso 1 1 calc R . . C16 C 0.8157(2) 0.26211(12) 0.72534(16) 0.0622(5) Uani 1 1 d . . . H16 H 0.9014 0.2887 0.7452 0.075 Uiso 1 1 calc R . . O2 O 0.9123(3) 0.38626(11) 0.4254(2) 0.1047(7) Uani 1 1 d . . . C10 C 1.1489(2) 0.24180(12) 0.57122(16) 0.0630(5) Uani 1 1 d . . . H10A H 1.1220 0.2821 0.6036 0.094 Uiso 1 1 calc R . . H10B H 1.2232 0.2535 0.5368 0.094 Uiso 1 1 calc R . . H10C H 1.1876 0.2077 0.6243 0.094 Uiso 1 1 calc R . . C12 C 0.6354(3) 0.19255(13) 0.77300(19) 0.0707(6) Uani 1 1 d . . . H12 H 0.5994 0.1718 0.8244 0.085 Uiso 1 1 calc R . . C22 C 1.2796(3) -0.02193(14) 0.4980(2) 0.0801(7) Uani 1 1 d . . . H22A H 1.3527 0.0119 0.5300 0.120 Uiso 1 1 calc R . . H22B H 1.3278 -0.0650 0.4945 0.120 Uiso 1 1 calc R . . H22C H 1.2110 -0.0272 0.5394 0.120 Uiso 1 1 calc R . . C11 C 0.7622(3) 0.23253(14) 0.80158(17) 0.0735(6) Uani 1 1 d . . . H11 H 0.8112 0.2393 0.8726 0.088 Uiso 1 1 calc R . . C18 C 0.7103(3) 0.33184(12) 0.4627(2) 0.0699(6) Uani 1 1 d . . . H18A H 0.6246 0.3065 0.4215 0.084 Uiso 1 1 calc R . . H18B H 0.6758 0.3672 0.5020 0.084 Uiso 1 1 calc R . . C21 C 1.2989(3) 0.02594(15) 0.32562(19) 0.0790(7) Uani 1 1 d . . . H21A H 1.2410 0.0466 0.2612 0.118 Uiso 1 1 calc R . . H21B H 1.3540 -0.0121 0.3095 0.118 Uiso 1 1 calc R . . H21C H 1.3665 0.0593 0.3664 0.118 Uiso 1 1 calc R . . C23 C 1.0919(3) -0.05351(13) 0.3302(3) 0.1027(11) Uani 1 1 d . . . H23A H 1.0236 -0.0652 0.3698 0.154 Uiso 1 1 calc R . . H23B H 1.1470 -0.0936 0.3217 0.154 Uiso 1 1 calc R . . H23C H 1.0378 -0.0364 0.2620 0.154 Uiso 1 1 calc R . . O3 O 0.7206(4) 0.36602(19) 0.2977(3) 0.1491(11) 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 Cl1 0.1178(5) 0.0885(5) 0.0466(3) -0.0214(2) 0.0204(3) -0.0007(3) O5 0.0438(6) 0.0373(6) 0.0575(7) -0.0071(5) 0.0075(5) 0.0080(4) N2 0.0396(7) 0.0393(7) 0.0433(6) -0.0101(5) 0.0053(5) 0.0022(5) O4 0.0412(6) 0.0629(9) 0.0737(8) -0.0219(7) 0.0041(6) 0.0053(5) N1 0.0369(6) 0.0422(7) 0.0414(6) -0.0068(5) 0.0058(5) 0.0046(5) O1 0.0426(6) 0.0713(9) 0.0673(8) -0.0191(7) 0.0031(6) 0.0147(6) C19 0.0417(8) 0.0439(9) 0.0397(7) -0.0055(6) 0.0081(6) 0.0056(6) C4 0.0413(7) 0.0334(7) 0.0374(7) -0.0007(5) 0.0063(6) 0.0040(6) C7 0.0436(8) 0.0436(9) 0.0472(8) -0.0060(7) 0.0082(6) 0.0088(7) C8 0.0461(8) 0.0361(8) 0.0456(8) -0.0075(6) 0.0100(6) 0.0027(6) C3 0.0477(9) 0.0467(9) 0.0502(8) 0.0003(7) 0.0123(7) -0.0074(7) C15 0.0428(9) 0.0482(9) 0.0603(10) -0.0182(8) 0.0112(7) 0.0090(7) C5 0.0526(9) 0.0491(9) 0.0424(8) -0.0031(7) 0.0127(7) -0.0086(7) C6 0.0584(10) 0.0494(10) 0.0477(9) -0.0085(7) 0.0058(8) -0.0111(8) C1 0.0682(11) 0.0530(10) 0.0363(7) -0.0068(7) 0.0098(7) 0.0028(8) C9 0.0479(8) 0.0372(8) 0.0515(8) -0.0083(6) 0.0118(7) 0.0064(6) C20 0.0578(10) 0.0448(10) 0.0653(11) -0.0075(8) 0.0094(8) 0.0200(8) C14 0.0459(9) 0.0558(11) 0.0640(10) -0.0186(9) 0.0061(8) 0.0055(8) C17 0.0510(9) 0.0452(9) 0.0691(11) -0.0171(8) 0.0171(8) 0.0063(7) C13 0.0509(10) 0.0555(12) 0.0845(14) -0.0124(10) 0.0170(9) 0.0021(8) N3 0.0985(17) 0.0535(11) 0.1115(18) 0.0141(11) 0.0437(14) 0.0245(11) C2 0.0643(11) 0.0657(12) 0.0464(9) 0.0018(8) 0.0238(8) -0.0013(9) C16 0.0460(9) 0.0706(13) 0.0649(11) -0.0224(10) 0.0074(8) 0.0005(8) O2 0.0888(13) 0.0785(13) 0.160(2) 0.0150(13) 0.0573(13) -0.0017(10) C10 0.0498(10) 0.0661(12) 0.0675(11) -0.0300(10) 0.0073(8) -0.0008(8) C12 0.0683(13) 0.0705(14) 0.0785(14) -0.0006(11) 0.0292(11) 0.0113(11) C22 0.0848(15) 0.0682(14) 0.0801(15) 0.0194(11) 0.0112(12) 0.0287(12) C11 0.0659(13) 0.0942(17) 0.0571(11) -0.0119(11) 0.0117(9) 0.0095(12) C18 0.0669(12) 0.0508(11) 0.0976(16) -0.0047(10) 0.0323(11) 0.0154(9) C21 0.0801(15) 0.0957(18) 0.0658(13) -0.0114(12) 0.0279(11) 0.0282(13) C23 0.0903(18) 0.0494(13) 0.148(3) -0.0376(15) 0.0006(18) 0.0133(12) O3 0.164(3) 0.162(3) 0.122(2) 0.0380(19) 0.040(2) 0.010(2) _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 Cl1 C1 1.7379(17) . ? O5 C19 1.310(2) . ? O5 C20 1.491(2) . ? N2 N1 1.3976(18) . ? N2 C8 1.398(2) . ? N2 C19 1.411(2) . ? O4 C19 1.1859(19) . ? N1 C7 1.391(2) . ? N1 C4 1.4210(19) . ? O1 C7 1.215(2) . ? C4 C3 1.369(2) . ? C4 C5 1.382(2) . ? C7 C9 1.445(2) . ? C8 C9 1.344(2) . ? C8 C10 1.474(2) . ? C3 C2 1.382(3) . ? C3 H3 0.9300 . ? C15 C14 1.381(3) . ? C15 C16 1.381(3) . ? C15 C17 1.523(3) . ? C5 C6 1.376(2) . ? C5 H5 0.9300 . ? C6 C1 1.367(3) . ? C6 H6 0.9300 . ? C1 C2 1.373(3) . ? C9 C17 1.500(2) . ? C20 C23 1.502(3) . ? C20 C22 1.504(3) . ? C20 C21 1.508(3) . ? C14 C13 1.377(3) . ? C14 H14 0.9300 . ? C17 C18 1.513(3) . ? C17 H17 0.9800 . ? C13 C12 1.368(3) . ? C13 H13 0.9300 . ? N3 O2 1.202(3) . ? N3 O3 1.214(3) . ? N3 C18 1.493(4) . ? C2 H2 0.9300 . ? C16 C11 1.370(3) . ? C16 H16 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C12 C11 1.383(4) . ? C12 H12 0.9300 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C11 H11 0.9300 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 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 C19 O5 C20 120.30(13) . . ? N1 N2 C8 107.73(12) . . ? N1 N2 C19 121.13(12) . . ? C8 N2 C19 123.06(12) . . ? C7 N1 N2 108.69(12) . . ? C7 N1 C4 122.40(12) . . ? N2 N1 C4 120.71(12) . . ? O4 C19 O5 128.64(15) . . ? O4 C19 N2 121.59(15) . . ? O5 C19 N2 109.73(12) . . ? C3 C4 C5 120.76(14) . . ? C3 C4 N1 121.28(14) . . ? C5 C4 N1 117.96(14) . . ? O1 C7 N1 123.62(14) . . ? O1 C7 C9 130.90(15) . . ? N1 C7 C9 105.47(13) . . ? C9 C8 N2 108.74(13) . . ? C9 C8 C10 128.83(15) . . ? N2 C8 C10 122.42(14) . . ? C4 C3 C2 119.29(16) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C14 C15 C16 118.7(2) . . ? C14 C15 C17 122.83(16) . . ? C16 C15 C17 118.39(17) . . ? C6 C5 C4 119.83(16) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C1 C6 C5 119.09(16) . . ? C1 C6 H6 120.5 . . ? C5 C6 H6 120.5 . . ? C6 C1 C2 121.43(15) . . ? C6 C1 Cl1 119.24(14) . . ? C2 C1 Cl1 119.34(14) . . ? C8 C9 C7 109.11(14) . . ? C8 C9 C17 126.06(15) . . ? C7 C9 C17 124.79(15) . . ? O5 C20 C23 101.49(16) . . ? O5 C20 C22 108.62(16) . . ? C23 C20 C22 111.8(2) . . ? O5 C20 C21 109.28(17) . . ? C23 C20 C21 112.1(2) . . ? C22 C20 C21 112.9(2) . . ? C13 C14 C15 120.21(17) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C9 C17 C18 110.48(17) . . ? C9 C17 C15 112.65(16) . . ? C18 C17 C15 112.40(16) . . ? C9 C17 H17 107.0 . . ? C18 C17 H17 107.0 . . ? C15 C17 H17 107.0 . . ? C12 C13 C14 120.9(2) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? O2 N3 O3 123.6(3) . . ? O2 N3 C18 120.1(3) . . ? O3 N3 C18 116.3(3) . . ? C1 C2 C3 119.54(16) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C11 C16 C15 120.99(19) . . ? C11 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C13 C12 C11 119.2(2) . . ? C13 C12 H12 120.4 . . ? C11 C12 H12 120.4 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C16 C11 C12 120.03(19) . . ? C16 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? N3 C18 C17 110.05(19) . . ? N3 C18 H18A 109.7 . . ? C17 C18 H18A 109.7 . . ? N3 C18 H18B 109.7 . . ? C17 C18 H18B 109.7 . . ? H18A C18 H18B 108.2 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? 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 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.424 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.062 data_20120328d_0m _database_code_depnum_ccdc_archive 'CCDC 874014' #TrackingRef '- 2a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H17 Cl N2 O3' _chemical_formula_weight 308.76 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' Cl Cl 0.1484 0.1585 '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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.3854(12) _cell_length_b 12.1629(13) _cell_length_c 12.6647(13) _cell_angle_alpha 97.717(2) _cell_angle_beta 95.368(2) _cell_angle_gamma 111.818(2) _cell_volume 1593.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.287 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.250 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11566 _diffrn_reflns_av_R_equivalents 0.0517 _diffrn_reflns_av_sigmaI/netI 0.0563 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 28.31 _reflns_number_total 7825 _reflns_number_gt 4594 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0404P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7825 _refine_ls_number_parameters 387 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0770 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1137 _refine_ls_wR_factor_gt 0.1033 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _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 Cl1 Cl 0.68892(6) -0.30831(4) 0.17850(4) 0.07935(17) Uani 1 1 d . . . O1 O 0.74516(11) 0.27123(10) 0.11190(8) 0.0550(3) Uani 1 1 d . . . O2 O 0.74269(13) 0.27700(14) 0.29033(9) 0.0840(4) Uani 1 1 d . . . O3 O 0.91885(11) 0.29924(10) 0.21379(8) 0.0524(3) Uani 1 1 d . . . N3 N 1.05536(14) 0.24075(13) 0.45187(10) 0.0588(4) Uani 1 1 d . . . N4 N 0.97937(13) 0.20851(12) 0.35263(9) 0.0511(3) Uani 1 1 d . . . C1 C 0.5189(2) 0.1503(2) 0.1172(2) 0.1051(8) Uani 1 1 d . . . H1A H 0.5396 0.0822 0.0941 0.158 Uiso 1 1 calc R . . H1B H 0.4332 0.1346 0.0849 0.158 Uiso 1 1 calc R . . H1C H 0.5249 0.1641 0.1944 0.158 Uiso 1 1 calc R . . C2 C 0.5978(2) 0.2459(3) -0.03875(16) 0.1207(10) Uani 1 1 d . . . H2A H 0.6620 0.3142 -0.0581 0.181 Uiso 1 1 calc R . . H2B H 0.5143 0.2406 -0.0673 0.181 Uiso 1 1 calc R . . H2C H 0.6085 0.1738 -0.0680 0.181 Uiso 1 1 calc R . . C3 C 0.61121(18) 0.26013(17) 0.08324(13) 0.0640(5) Uani 1 1 d . . . C4 C 0.6006(2) 0.3742(2) 0.1356(2) 0.0999(8) Uani 1 1 d . . . H4A H 0.6103 0.3794 0.2124 0.150 Uiso 1 1 calc R . . H4B H 0.5182 0.3734 0.1098 0.150 Uiso 1 1 calc R . . H4C H 0.6665 0.4425 0.1179 0.150 Uiso 1 1 calc R . . C5 C 0.79278(17) 0.28189(14) 0.21278(12) 0.0488(4) Uani 1 1 d . . . C6 C 0.98506(16) 0.30872(15) 0.31396(12) 0.0510(4) Uani 1 1 d . . . C7 C 1.06437(18) 0.40622(15) 0.38514(13) 0.0618(5) Uani 1 1 d . . . H7 H 1.0865 0.4866 0.3794 0.074 Uiso 1 1 calc R . . C8 C 1.10645(18) 0.36024(16) 0.47008(13) 0.0614(5) Uani 1 1 d . . . C9 C 1.1991(2) 0.42801(18) 0.57087(15) 0.0865(7) Uani 1 1 d . . . H9A H 1.1940 0.3749 0.6215 0.130 Uiso 1 1 calc R . . H9B H 1.1783 0.4936 0.6020 0.130 Uiso 1 1 calc R . . H9C H 1.2844 0.4590 0.5538 0.130 Uiso 1 1 calc R . . C10 C 0.90630(15) 0.08541(14) 0.30898(11) 0.0465(4) Uani 1 1 d . . . C11 C 0.85641(17) 0.00692(15) 0.37804(12) 0.0564(4) Uani 1 1 d . . . H11 H 0.8677 0.0360 0.4516 0.068 Uiso 1 1 calc R . . C12 C 0.81934(17) -0.07794(15) 0.15886(12) 0.0546(4) Uani 1 1 d . . . H12 H 0.8059 -0.1072 0.0852 0.066 Uiso 1 1 calc R . . C13 C 0.88738(16) 0.04236(15) 0.19901(12) 0.0516(4) Uani 1 1 d . . . H13 H 0.9208 0.0950 0.1525 0.062 Uiso 1 1 calc R . . C14 C 0.77127(16) -0.15462(14) 0.22884(13) 0.0536(4) Uani 1 1 d . . . C15 C 0.79061(18) -0.11321(16) 0.33859(13) 0.0607(5) Uani 1 1 d . . . H15 H 0.7592 -0.1665 0.3851 0.073 Uiso 1 1 calc R . . Cl2 Cl -0.00674(6) -0.41307(5) 0.16138(5) 0.0933(2) Uani 1 1 d . . . O4 O 0.32882(11) 0.16166(10) 0.38915(8) 0.0611(3) Uani 1 1 d . . . O5 O 0.51341(14) 0.32571(13) 0.43532(11) 0.0912(5) Uani 1 1 d . . . O6 O 0.46237(11) 0.16674(10) 0.52131(8) 0.0561(3) Uani 1 1 d . . . N1 N 0.21416(13) 0.11738(12) 0.21659(9) 0.0485(3) Uani 1 1 d . . . N2 N 0.18379(14) 0.17149(12) 0.13511(10) 0.0538(3) Uani 1 1 d . . . C16 C 0.05692(17) -0.25652(15) 0.17820(14) 0.0578(4) Uani 1 1 d . . . C17 C 0.10239(18) -0.20269(16) 0.09296(14) 0.0640(5) Uani 1 1 d . . . H17 H 0.0969 -0.2496 0.0269 0.077 Uiso 1 1 calc R . . C18 C 0.15590(17) -0.07904(15) 0.10656(12) 0.0579(4) Uani 1 1 d . . . H18 H 0.1878 -0.0420 0.0498 0.069 Uiso 1 1 calc R . . C19 C 0.16225(15) -0.00978(14) 0.20471(11) 0.0455(4) Uani 1 1 d . . . C20 C 0.11459(15) -0.06496(15) 0.28875(12) 0.0507(4) Uani 1 1 d . . . H20 H 0.1181 -0.0185 0.3545 0.061 Uiso 1 1 calc R . . C21 C 0.06180(16) -0.18877(16) 0.27514(13) 0.0558(4) Uani 1 1 d . . . H21 H 0.0296 -0.2261 0.3316 0.067 Uiso 1 1 calc R . . C22 C 0.28924(16) 0.20226(15) 0.30166(11) 0.0498(4) Uani 1 1 d . . . C23 C 0.30878(18) 0.31243(16) 0.27831(13) 0.0587(4) Uani 1 1 d . . . H23 H 0.3565 0.3871 0.3216 0.070 Uiso 1 1 calc R . . C24 C 0.24070(17) 0.28838(15) 0.17397(12) 0.0542(4) Uani 1 1 d . . . C25 C 0.2273(2) 0.37756(17) 0.10779(15) 0.0740(6) Uani 1 1 d . . . H25A H 0.1832 0.3361 0.0368 0.111 Uiso 1 1 calc R . . H25B H 0.3108 0.4347 0.1028 0.111 Uiso 1 1 calc R . . H25C H 0.1795 0.4190 0.1414 0.111 Uiso 1 1 calc R . . C26 C 0.44560(18) 0.22980(16) 0.44888(12) 0.0542(4) Uani 1 1 d . . . C27 C 0.5615(2) 0.11358(18) 0.66471(14) 0.0789(6) Uani 1 1 d . . . H27A H 0.4891 0.1079 0.7001 0.118 Uiso 1 1 calc R . . H27B H 0.6356 0.1331 0.7178 0.118 Uiso 1 1 calc R . . H27C H 0.5443 0.0379 0.6191 0.118 Uiso 1 1 calc R . . C28 C 0.58623(17) 0.21109(16) 0.59701(12) 0.0584(4) Uani 1 1 d . . . C29 C 0.6079(2) 0.33017(18) 0.66497(15) 0.0886(7) Uani 1 1 d . . . H29A H 0.6224 0.3902 0.6202 0.133 Uiso 1 1 calc R . . H29B H 0.6814 0.3531 0.7196 0.133 Uiso 1 1 calc R . . H29C H 0.5339 0.3232 0.6985 0.133 Uiso 1 1 calc R . . C30 C 0.6929(2) 0.2181(2) 0.53224(15) 0.0910(7) Uani 1 1 d . . . H30A H 0.6736 0.1407 0.4889 0.136 Uiso 1 1 calc R . . H30B H 0.7719 0.2418 0.5804 0.136 Uiso 1 1 calc R . . H30C H 0.7009 0.2763 0.4863 0.136 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 Cl1 0.0905(4) 0.0557(3) 0.0858(3) 0.0092(2) 0.0061(3) 0.0246(3) O1 0.0599(8) 0.0769(8) 0.0400(6) 0.0163(5) 0.0107(5) 0.0374(6) O2 0.0769(10) 0.1430(13) 0.0449(7) 0.0210(7) 0.0213(6) 0.0530(9) O3 0.0564(8) 0.0670(7) 0.0442(6) 0.0226(5) 0.0115(5) 0.0308(6) N3 0.0664(10) 0.0639(9) 0.0435(7) 0.0132(6) -0.0034(6) 0.0239(8) N4 0.0624(9) 0.0538(8) 0.0390(7) 0.0123(6) 0.0025(6) 0.0246(7) C1 0.0705(17) 0.0926(17) 0.1254(19) 0.0030(14) 0.0065(14) 0.0094(13) C2 0.103(2) 0.220(3) 0.0598(13) 0.0190(15) -0.0063(12) 0.093(2) C3 0.0558(12) 0.0809(13) 0.0590(10) 0.0097(9) 0.0027(8) 0.0335(10) C4 0.0819(17) 0.1000(17) 0.134(2) 0.0074(15) 0.0067(15) 0.0601(14) C5 0.0575(11) 0.0518(9) 0.0416(9) 0.0104(7) 0.0095(8) 0.0253(8) C6 0.0569(11) 0.0586(10) 0.0436(8) 0.0173(8) 0.0085(7) 0.0266(9) C7 0.0715(13) 0.0524(10) 0.0593(10) 0.0143(8) 0.0056(9) 0.0214(9) C8 0.0676(13) 0.0602(11) 0.0498(9) 0.0101(8) 0.0026(8) 0.0191(9) C9 0.0943(17) 0.0772(14) 0.0653(12) 0.0093(10) -0.0129(11) 0.0149(12) C10 0.0499(10) 0.0540(9) 0.0421(8) 0.0145(7) 0.0063(7) 0.0258(8) C11 0.0725(13) 0.0621(11) 0.0421(8) 0.0142(8) 0.0188(8) 0.0307(9) C12 0.0637(12) 0.0637(11) 0.0423(8) 0.0095(8) 0.0034(8) 0.0327(9) C13 0.0600(11) 0.0590(10) 0.0425(8) 0.0175(7) 0.0073(7) 0.0279(9) C14 0.0526(11) 0.0509(10) 0.0609(10) 0.0112(8) 0.0063(8) 0.0246(8) C15 0.0735(13) 0.0604(11) 0.0574(10) 0.0238(8) 0.0253(9) 0.0287(10) Cl2 0.1028(5) 0.0586(3) 0.1168(5) 0.0253(3) 0.0184(3) 0.0262(3) O4 0.0632(8) 0.0625(7) 0.0516(6) 0.0166(5) -0.0082(6) 0.0197(6) O5 0.0726(10) 0.0840(10) 0.1005(10) 0.0451(8) -0.0132(8) 0.0086(8) O6 0.0616(8) 0.0613(7) 0.0437(6) 0.0114(5) -0.0026(5) 0.0239(6) N1 0.0526(9) 0.0561(8) 0.0403(7) 0.0177(6) 0.0055(6) 0.0224(7) N2 0.0598(9) 0.0644(9) 0.0448(7) 0.0223(6) 0.0082(6) 0.0287(7) C16 0.0511(11) 0.0560(10) 0.0697(11) 0.0208(9) 0.0070(8) 0.0220(8) C17 0.0721(13) 0.0626(12) 0.0553(10) 0.0058(8) 0.0117(9) 0.0254(10) C18 0.0641(12) 0.0657(11) 0.0445(9) 0.0176(8) 0.0147(8) 0.0219(9) C19 0.0423(9) 0.0549(9) 0.0426(8) 0.0158(7) 0.0045(7) 0.0209(7) C20 0.0494(10) 0.0666(11) 0.0430(8) 0.0189(7) 0.0078(7) 0.0273(9) C21 0.0501(11) 0.0687(11) 0.0551(10) 0.0307(9) 0.0096(8) 0.0234(9) C22 0.0530(10) 0.0592(10) 0.0427(8) 0.0138(7) 0.0047(7) 0.0272(8) C23 0.0683(12) 0.0578(10) 0.0553(10) 0.0096(8) 0.0035(8) 0.0323(9) C24 0.0609(11) 0.0619(11) 0.0522(9) 0.0205(8) 0.0141(8) 0.0332(9) C25 0.0940(16) 0.0735(13) 0.0720(12) 0.0329(10) 0.0125(11) 0.0459(12) C26 0.0581(12) 0.0618(11) 0.0457(9) 0.0110(8) 0.0026(8) 0.0278(9) C27 0.0922(16) 0.0929(15) 0.0546(11) 0.0221(10) -0.0035(10) 0.0400(12) C28 0.0607(12) 0.0746(12) 0.0389(8) 0.0070(8) -0.0032(8) 0.0290(9) C29 0.1033(18) 0.0837(15) 0.0639(12) -0.0083(10) -0.0078(11) 0.0319(13) C30 0.0759(15) 0.153(2) 0.0637(12) 0.0323(13) 0.0155(11) 0.0620(15) _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 Cl1 C14 1.7451(17) . ? O1 C5 1.3102(17) . ? O1 C3 1.485(2) . ? O2 C5 1.1784(17) . ? O3 C5 1.3695(19) . ? O3 C6 1.3813(18) . ? N3 C8 1.327(2) . ? N3 N4 1.3762(17) . ? N4 C6 1.3554(19) . ? N4 C10 1.4161(19) . ? C1 C3 1.507(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.518(3) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.507(3) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C6 C7 1.341(2) . ? C7 C8 1.401(2) . ? C7 H7 0.9300 . ? C8 C9 1.497(2) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.383(2) . ? C10 C13 1.387(2) . ? C11 C15 1.366(2) . ? C11 H11 0.9300 . ? C12 C13 1.372(2) . ? C12 C14 1.374(2) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.381(2) . ? C15 H15 0.9300 . ? Cl2 C16 1.7415(17) . ? O4 C26 1.3606(19) . ? O4 C22 1.3761(17) . ? O5 C26 1.1813(19) . ? O6 C26 1.3157(19) . ? O6 C28 1.4972(19) . ? N1 C22 1.3529(19) . ? N1 N2 1.3792(16) . ? N1 C19 1.4162(19) . ? N2 C24 1.323(2) . ? C16 C21 1.368(2) . ? C16 C17 1.380(2) . ? C17 C18 1.376(2) . ? C17 H17 0.9300 . ? C18 C19 1.384(2) . ? C18 H18 0.9300 . ? C19 C20 1.381(2) . ? C20 C21 1.377(2) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C23 1.353(2) . ? C23 C24 1.403(2) . ? C23 H23 0.9300 . ? C24 C25 1.498(2) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C27 C28 1.514(2) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 C29 1.503(3) . ? C28 C30 1.511(2) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 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 C5 O1 C3 120.14(12) . . ? C5 O3 C6 114.83(12) . . ? C8 N3 N4 104.80(13) . . ? C6 N4 N3 109.77(13) . . ? C6 N4 C10 130.17(13) . . ? N3 N4 C10 120.00(12) . . ? C3 C1 H1A 109.5 . . ? C3 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C3 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 H2A 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C3 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? O1 C3 C1 110.56(16) . . ? O1 C3 C4 108.41(15) . . ? C1 C3 C4 111.96(19) . . ? O1 C3 C2 101.50(15) . . ? C1 C3 C2 111.27(19) . . ? C4 C3 C2 112.61(19) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O2 C5 O1 129.82(17) . . ? O2 C5 O3 123.94(14) . . ? O1 C5 O3 106.23(12) . . ? C7 C6 N4 108.98(14) . . ? C7 C6 O3 130.51(15) . . ? N4 C6 O3 120.46(14) . . ? C6 C7 C8 104.82(15) . . ? C6 C7 H7 127.6 . . ? C8 C7 H7 127.6 . . ? N3 C8 C7 111.63(15) . . ? N3 C8 C9 119.93(16) . . ? C7 C8 C9 128.42(17) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C13 119.90(15) . . ? C11 C10 N4 119.04(13) . . ? C13 C10 N4 121.04(13) . . ? C15 C11 C10 120.23(15) . . ? C15 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C13 C12 C14 119.21(15) . . ? C13 C12 H12 120.4 . . ? C14 C12 H12 120.4 . . ? C12 C13 C10 120.03(14) . . ? C12 C13 H13 120.0 . . ? C10 C13 H13 120.0 . . ? C12 C14 C15 121.36(15) . . ? C12 C14 Cl1 119.31(13) . . ? C15 C14 Cl1 119.29(13) . . ? C11 C15 C14 119.24(15) . . ? C11 C15 H15 120.4 . . ? C14 C15 H15 120.4 . . ? C26 O4 C22 118.40(13) . . ? C26 O6 C28 120.26(13) . . ? C22 N1 N2 110.03(12) . . ? C22 N1 C19 129.93(12) . . ? N2 N1 C19 119.96(12) . . ? C24 N2 N1 104.60(12) . . ? C21 C16 C17 120.97(16) . . ? C21 C16 Cl2 119.91(13) . . ? C17 C16 Cl2 119.12(14) . . ? C18 C17 C16 119.43(16) . . ? C18 C17 H17 120.3 . . ? C16 C17 H17 120.3 . . ? C17 C18 C19 119.97(14) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C20 C19 C18 119.93(15) . . ? C20 C19 N1 120.68(14) . . ? C18 C19 N1 119.36(13) . . ? C21 C20 C19 119.98(15) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C16 C21 C20 119.70(14) . . ? C16 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C23 C22 N1 108.88(13) . . ? C23 C22 O4 134.40(15) . . ? N1 C22 O4 116.72(13) . . ? C22 C23 C24 104.30(15) . . ? C22 C23 H23 127.8 . . ? C24 C23 H23 127.8 . . ? N2 C24 C23 112.18(14) . . ? N2 C24 C25 120.16(15) . . ? C23 C24 C25 127.65(16) . . ? 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 . . ? O5 C26 O6 129.67(17) . . ? O5 C26 O4 124.76(15) . . ? O6 C26 O4 105.57(14) . . ? C28 C27 H27A 109.5 . . ? C28 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C28 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O6 C28 C29 109.79(15) . . ? O6 C28 C30 108.87(13) . . ? C29 C28 C30 112.61(17) . . ? O6 C28 C27 101.87(14) . . ? C29 C28 C27 111.01(15) . . ? C30 C28 C27 112.13(17) . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 C30 H30A 109.5 . . ? C28 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C28 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 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 C8 N3 N4 C6 -0.72(18) . . . . ? C8 N3 N4 C10 -178.09(14) . . . . ? C5 O1 C3 C1 -60.0(2) . . . . ? C5 O1 C3 C4 63.1(2) . . . . ? C5 O1 C3 C2 -178.10(16) . . . . ? C3 O1 C5 O2 5.3(3) . . . . ? C3 O1 C5 O3 -175.57(12) . . . . ? C6 O3 C5 O2 1.2(2) . . . . ? C6 O3 C5 O1 -178.02(12) . . . . ? N3 N4 C6 C7 0.69(19) . . . . ? C10 N4 C6 C7 177.71(16) . . . . ? N3 N4 C6 O3 178.40(14) . . . . ? C10 N4 C6 O3 -4.6(3) . . . . ? C5 O3 C6 C7 -99.2(2) . . . . ? C5 O3 C6 N4 83.62(18) . . . . ? N4 C6 C7 C8 -0.4(2) . . . . ? O3 C6 C7 C8 -177.77(17) . . . . ? N4 N3 C8 C7 0.5(2) . . . . ? N4 N3 C8 C9 -178.19(17) . . . . ? C6 C7 C8 N3 -0.1(2) . . . . ? C6 C7 C8 C9 178.5(2) . . . . ? C6 N4 C10 C11 -142.87(17) . . . . ? N3 N4 C10 C11 33.9(2) . . . . ? C6 N4 C10 C13 38.9(2) . . . . ? N3 N4 C10 C13 -144.30(16) . . . . ? C13 C10 C11 C15 1.2(3) . . . . ? N4 C10 C11 C15 -176.98(15) . . . . ? C14 C12 C13 C10 -0.4(3) . . . . ? C11 C10 C13 C12 0.0(2) . . . . ? N4 C10 C13 C12 178.12(15) . . . . ? C13 C12 C14 C15 -0.3(3) . . . . ? C13 C12 C14 Cl1 -178.06(13) . . . . ? C10 C11 C15 C14 -1.9(3) . . . . ? C12 C14 C15 C11 1.5(3) . . . . ? Cl1 C14 C15 C11 179.23(14) . . . . ? C22 N1 N2 C24 -0.64(17) . . . . ? C19 N1 N2 C24 176.41(13) . . . . ? C21 C16 C17 C18 1.4(3) . . . . ? Cl2 C16 C17 C18 -178.29(14) . . . . ? C16 C17 C18 C19 -0.8(3) . . . . ? C17 C18 C19 C20 -0.1(3) . . . . ? C17 C18 C19 N1 -178.15(15) . . . . ? C22 N1 C19 C20 40.1(2) . . . . ? N2 N1 C19 C20 -136.28(15) . . . . ? C22 N1 C19 C18 -141.90(17) . . . . ? N2 N1 C19 C18 41.7(2) . . . . ? C18 C19 C20 C21 0.6(2) . . . . ? N1 C19 C20 C21 178.54(14) . . . . ? C17 C16 C21 C20 -1.0(3) . . . . ? Cl2 C16 C21 C20 178.69(13) . . . . ? C19 C20 C21 C16 0.0(2) . . . . ? N2 N1 C22 C23 0.38(19) . . . . ? C19 N1 C22 C23 -176.29(15) . . . . ? N2 N1 C22 O4 -179.21(13) . . . . ? C19 N1 C22 O4 4.1(2) . . . . ? C26 O4 C22 C23 -31.9(3) . . . . ? C26 O4 C22 N1 147.58(15) . . . . ? N1 C22 C23 C24 0.03(19) . . . . ? O4 C22 C23 C24 179.52(18) . . . . ? N1 N2 C24 C23 0.67(18) . . . . ? N1 N2 C24 C25 -178.99(15) . . . . ? C22 C23 C24 N2 -0.5(2) . . . . ? C22 C23 C24 C25 179.18(17) . . . . ? C28 O6 C26 O5 -4.8(3) . . . . ? C28 O6 C26 O4 175.77(13) . . . . ? C22 O4 C26 O5 4.8(3) . . . . ? C22 O4 C26 O6 -175.75(13) . . . . ? C26 O6 C28 C29 61.36(19) . . . . ? C26 O6 C28 C30 -62.3(2) . . . . ? C26 O6 C28 C27 179.07(14) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.186 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.049 # Attachment '- 7h.cif' data_20120214e_0m _database_code_depnum_ccdc_archive 'CCDC 874398' #TrackingRef '- 7h.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H19 Br Cl N3 O4' _chemical_formula_sum 'C21 H19 Br Cl N3 O4' _chemical_formula_weight 492.75 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' 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 11.936(2) _cell_length_b 9.6365(17) _cell_length_c 21.342(3) _cell_angle_alpha 90.00 _cell_angle_beta 116.511(7) _cell_angle_gamma 90.00 _cell_volume 2196.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 2372 _cell_measurement_theta_min 2.11 _cell_measurement_theta_max 25.15 _exptl_crystal_description ? _exptl_crystal_colour ? _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 1.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 2.025 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6211 _exptl_absorpt_correction_T_max 0.6875 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Aepex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12888 _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_sigmaI/netI 0.0389 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 25.99 _reflns_number_total 4304 _reflns_number_gt 3330 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0910P)^2^+1.1671P] 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 4304 _refine_ls_number_parameters 274 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0667 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.1493 _refine_ls_wR_factor_gt 0.1401 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 Br1 Br 0.20473(4) -0.23067(5) -0.10822(2) 0.06066(19) Uani 1 1 d . . . Cl2 Cl -0.22659(9) 0.65218(12) 0.17205(6) 0.0547(3) Uani 1 1 d . . . O1 O 0.0527(2) 0.1755(3) 0.03629(12) 0.0487(7) Uani 1 1 d . . . O2 O 0.19966(19) 0.2073(2) 0.14774(10) 0.0301(5) Uani 1 1 d . . . O3 O 0.6111(3) 0.3647(4) 0.24479(17) 0.0700(9) Uani 1 1 d . . . O4 O 0.5003(4) 0.2723(4) 0.29249(17) 0.0745(10) Uani 1 1 d . . . N1 N 0.1854(2) 0.4470(3) 0.11398(12) 0.0271(5) Uani 1 1 d . . . N2 N 0.2485(2) 0.5399(3) 0.09348(13) 0.0316(6) Uani 1 1 d . . . N3 N 0.5404(3) 0.2752(4) 0.24906(18) 0.0517(9) Uani 1 1 d . . . C1 C 0.0842(3) 0.4925(3) 0.12721(15) 0.0271(6) Uani 1 1 d . . . C2 C -0.0002(3) 0.5883(3) 0.08225(16) 0.0333(7) Uani 1 1 d . . . H2 H 0.0076 0.6187 0.0430 0.040 Uiso 1 1 calc R . . C3 C -0.0954(3) 0.6384(4) 0.09571(18) 0.0383(7) Uani 1 1 d . . . H3 H -0.1523 0.7027 0.0658 0.046 Uiso 1 1 calc R . . C4 C -0.1048(3) 0.5915(4) 0.15430(18) 0.0374(7) Uani 1 1 d . . . C5 C -0.0215(3) 0.4946(4) 0.19925(17) 0.0369(7) Uani 1 1 d . . . H5 H -0.0301 0.4635 0.2381 0.044 Uiso 1 1 calc R . . C6 C 0.0737(3) 0.4450(4) 0.18604(15) 0.0335(7) Uani 1 1 d . . . H6 H 0.1304 0.3806 0.2159 0.040 Uiso 1 1 calc R . . C7 C 0.2745(3) -0.0918(4) -0.03790(17) 0.0388(8) Uani 1 1 d . . . C8 C 0.3239(3) 0.0286(4) -0.05122(17) 0.0403(8) Uani 1 1 d . . . H8 H 0.3200 0.0436 -0.0952 0.048 Uiso 1 1 calc R . . C9 C 0.3786(3) 0.1258(4) 0.00093(16) 0.0353(7) Uani 1 1 d . . . H9 H 0.4126 0.2060 -0.0079 0.042 Uiso 1 1 calc R . . C10 C 0.3837(3) 0.1055(3) 0.06681(15) 0.0294(6) Uani 1 1 d . . . C11 C 0.3315(3) -0.0149(4) 0.07858(17) 0.0357(7) Uani 1 1 d . . . H11 H 0.3331 -0.0291 0.1221 0.043 Uiso 1 1 calc R . . C12 C 0.2770(3) -0.1142(4) 0.02648(18) 0.0376(7) Uani 1 1 d . . . H12 H 0.2427 -0.1945 0.0349 0.045 Uiso 1 1 calc R . . C13 C 0.4405(3) 0.2192(3) 0.12181(16) 0.0312(7) Uani 1 1 d . . . H13 H 0.5073 0.2633 0.1141 0.037 Uiso 1 1 calc R . . C16 C 0.0716(3) 0.0046(4) 0.12237(19) 0.0438(8) Uani 1 1 d . . . H16A H 0.0110 0.0247 0.1392 0.066 Uiso 1 1 calc R . . H16B H 0.1466 -0.0304 0.1601 0.066 Uiso 1 1 calc R . . H16C H 0.0382 -0.0638 0.0859 0.066 Uiso 1 1 calc R . . C17 C 0.1007(3) 0.1333(4) 0.09428(16) 0.0330(7) Uani 1 1 d . . . C18 C 0.3444(3) 0.4704(3) 0.09320(16) 0.0325(7) Uani 1 1 d . . . C19 C 0.4342(3) 0.5413(4) 0.0713(2) 0.0471(9) Uani 1 1 d . . . H19A H 0.4080 0.5254 0.0223 0.071 Uiso 1 1 calc R . . H19B H 0.5168 0.5044 0.0979 0.071 Uiso 1 1 calc R . . H19C H 0.4348 0.6392 0.0798 0.071 Uiso 1 1 calc R . . C20 C 0.3459(3) 0.3299(3) 0.11357(14) 0.0278(6) Uani 1 1 d . . . C21 C 0.2427(3) 0.3206(3) 0.12614(15) 0.0278(6) Uani 1 1 d . . . C22 C 0.5009(3) 0.1587(4) 0.19641(15) 0.0349(7) Uani 1 1 d . . . H22 H 0.4388 0.1014 0.2027 0.042 Uiso 1 1 calc R . . C23 C 0.6175(3) 0.0698(4) 0.21230(19) 0.0449(9) Uani 1 1 d . . . H23A H 0.6782 0.1243 0.2052 0.067 Uiso 1 1 calc R . . H23B H 0.5943 -0.0091 0.1816 0.067 Uiso 1 1 calc R . . H23C H 0.6528 0.0387 0.2600 0.067 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 0.0605(3) 0.0604(3) 0.0490(3) -0.02700(19) 0.0136(2) -0.0116(2) Cl2 0.0419(5) 0.0671(7) 0.0613(6) -0.0119(5) 0.0285(5) 0.0043(4) O1 0.0479(14) 0.0496(16) 0.0269(12) 0.0074(11) -0.0029(11) -0.0112(12) O2 0.0325(11) 0.0302(11) 0.0214(10) 0.0023(8) 0.0064(9) -0.0026(9) O3 0.069(2) 0.061(2) 0.0550(18) -0.0161(15) 0.0047(16) -0.0111(17) O4 0.097(3) 0.086(3) 0.0360(16) -0.0178(15) 0.0251(18) 0.010(2) N1 0.0246(11) 0.0308(13) 0.0224(12) 0.0036(10) 0.0074(10) 0.0013(10) N2 0.0299(12) 0.0324(14) 0.0253(12) 0.0048(10) 0.0059(10) 0.0013(11) N3 0.0508(19) 0.047(2) 0.0339(17) -0.0047(14) -0.0019(15) 0.0099(16) C1 0.0270(14) 0.0286(16) 0.0202(14) -0.0019(11) 0.0055(11) -0.0011(12) C2 0.0329(15) 0.0369(18) 0.0247(15) 0.0033(12) 0.0080(13) 0.0039(13) C3 0.0343(17) 0.0384(19) 0.0360(17) 0.0047(14) 0.0102(14) 0.0051(14) C4 0.0295(15) 0.0414(19) 0.0380(18) -0.0108(14) 0.0121(14) -0.0012(14) C5 0.0360(16) 0.047(2) 0.0264(15) -0.0048(14) 0.0127(13) -0.0048(14) C6 0.0325(15) 0.0393(18) 0.0206(14) -0.0001(12) 0.0047(12) -0.0004(13) C7 0.0320(16) 0.043(2) 0.0319(17) -0.0090(14) 0.0058(13) 0.0052(14) C8 0.0424(18) 0.048(2) 0.0250(16) -0.0029(14) 0.0101(14) 0.0055(16) C9 0.0342(16) 0.0372(18) 0.0285(15) 0.0018(13) 0.0087(13) 0.0030(13) C10 0.0224(13) 0.0331(16) 0.0234(14) 0.0009(12) 0.0018(11) 0.0077(12) C11 0.0325(15) 0.0428(19) 0.0273(16) 0.0026(13) 0.0093(13) 0.0059(14) C12 0.0311(16) 0.0383(19) 0.0390(18) 0.0014(14) 0.0116(14) 0.0002(14) C13 0.0272(14) 0.0370(17) 0.0212(14) 0.0003(12) 0.0034(12) 0.0024(13) C16 0.0459(19) 0.042(2) 0.0390(19) 0.0039(15) 0.0149(16) -0.0067(16) C17 0.0300(15) 0.0354(18) 0.0279(16) 0.0019(13) 0.0078(13) 0.0003(13) C18 0.0279(14) 0.0363(18) 0.0286(15) -0.0002(13) 0.0083(12) 0.0010(13) C19 0.0407(18) 0.049(2) 0.055(2) 0.0097(18) 0.0243(17) 0.0012(16) C20 0.0251(14) 0.0321(16) 0.0194(13) -0.0006(11) 0.0039(11) 0.0011(12) C21 0.0297(14) 0.0285(16) 0.0187(13) 0.0009(11) 0.0049(11) 0.0010(12) C22 0.0335(16) 0.0403(18) 0.0193(14) -0.0042(13) 0.0014(12) 0.0043(14) C23 0.0354(17) 0.050(2) 0.0360(18) 0.0019(16) 0.0039(15) 0.0095(16) _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 C7 1.903(3) . ? Cl2 C4 1.758(3) . ? O1 C17 1.180(4) . ? O2 C21 1.371(4) . ? O2 C17 1.415(4) . ? O3 N3 1.238(5) . ? O4 N3 1.218(5) . ? N1 N2 1.362(4) . ? N1 C21 1.364(4) . ? N1 C1 1.426(4) . ? N2 C18 1.329(4) . ? N3 C22 1.507(5) . ? C1 C2 1.387(4) . ? C1 C6 1.393(4) . ? C2 C3 1.378(5) . ? C2 H2 0.9300 . ? C3 C4 1.381(5) . ? C3 H3 0.9300 . ? C4 C5 1.389(5) . ? C5 C6 1.373(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C12 1.378(5) . ? C7 C8 1.387(5) . ? C8 C9 1.376(5) . ? C8 H8 0.9300 . ? C9 C10 1.394(4) . ? C9 H9 0.9300 . ? C10 C11 1.392(5) . ? C10 C13 1.526(4) . ? C11 C12 1.389(5) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C20 1.506(4) . ? C13 C22 1.539(4) . ? C13 H13 0.9800 . ? C16 C17 1.485(5) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C18 C20 1.420(5) . ? C18 C19 1.510(5) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C21 1.375(4) . ? C22 C23 1.538(5) . ? C22 H22 0.9800 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 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 C21 O2 C17 115.7(2) . . ? N2 N1 C21 110.2(2) . . ? N2 N1 C1 120.0(3) . . ? C21 N1 C1 129.4(3) . . ? C18 N2 N1 105.7(3) . . ? O4 N3 O3 125.7(4) . . ? O4 N3 C22 116.9(4) . . ? O3 N3 C22 117.4(4) . . ? C2 C1 C6 120.8(3) . . ? C2 C1 N1 119.0(3) . . ? C6 C1 N1 120.1(3) . . ? C3 C2 C1 120.0(3) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 118.8(3) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C3 C4 C5 121.5(3) . . ? C3 C4 Cl2 119.7(3) . . ? C5 C4 Cl2 118.7(3) . . ? C6 C5 C4 119.7(3) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C1 119.1(3) . . ? C5 C6 H6 120.5 . . ? C1 C6 H6 120.5 . . ? C12 C7 C8 120.9(3) . . ? C12 C7 Br1 118.9(3) . . ? C8 C7 Br1 120.2(3) . . ? C9 C8 C7 119.7(3) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C10 120.8(3) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C11 C10 C9 118.5(3) . . ? C11 C10 C13 122.7(3) . . ? C9 C10 C13 118.7(3) . . ? C12 C11 C10 121.1(3) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C7 C12 C11 119.0(3) . . ? C7 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C20 C13 C10 111.5(2) . . ? C20 C13 C22 111.7(3) . . ? C10 C13 C22 111.5(3) . . ? C20 C13 H13 107.3 . . ? C10 C13 H13 107.3 . . ? C22 C13 H13 107.3 . . ? C17 C16 H16A 109.5 . . ? C17 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C17 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O1 C17 O2 120.8(3) . . ? O1 C17 C16 128.3(3) . . ? O2 C17 C16 110.9(3) . . ? N2 C18 C20 111.9(3) . . ? N2 C18 C19 120.4(3) . . ? C20 C18 C19 127.8(3) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C21 C20 C18 103.4(3) . . ? C21 C20 C13 128.4(3) . . ? C18 C20 C13 128.1(3) . . ? N1 C21 O2 122.9(3) . . ? N1 C21 C20 108.8(3) . . ? O2 C21 C20 128.3(3) . . ? N3 C22 C23 107.4(3) . . ? N3 C22 C13 109.6(3) . . ? C23 C22 C13 113.5(3) . . ? N3 C22 H22 108.7 . . ? C23 C22 H22 108.7 . . ? C13 C22 H22 108.7 . . ? 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 . . ? 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 C21 N1 N2 C18 -0.1(3) . . . . ? C1 N1 N2 C18 173.1(3) . . . . ? N2 N1 C1 C2 41.5(4) . . . . ? C21 N1 C1 C2 -146.8(3) . . . . ? N2 N1 C1 C6 -136.1(3) . . . . ? C21 N1 C1 C6 35.6(4) . . . . ? C6 C1 C2 C3 0.4(5) . . . . ? N1 C1 C2 C3 -177.1(3) . . . . ? C1 C2 C3 C4 0.0(5) . . . . ? C2 C3 C4 C5 -0.6(5) . . . . ? C2 C3 C4 Cl2 -179.2(3) . . . . ? C3 C4 C5 C6 0.8(5) . . . . ? Cl2 C4 C5 C6 179.5(3) . . . . ? C4 C5 C6 C1 -0.4(5) . . . . ? C2 C1 C6 C5 -0.2(5) . . . . ? N1 C1 C6 C5 177.3(3) . . . . ? C12 C7 C8 C9 1.4(5) . . . . ? Br1 C7 C8 C9 -177.4(3) . . . . ? C7 C8 C9 C10 -0.8(5) . . . . ? C8 C9 C10 C11 -0.4(5) . . . . ? C8 C9 C10 C13 -177.5(3) . . . . ? C9 C10 C11 C12 1.0(5) . . . . ? C13 C10 C11 C12 177.9(3) . . . . ? C8 C7 C12 C11 -0.9(5) . . . . ? Br1 C7 C12 C11 178.0(2) . . . . ? C10 C11 C12 C7 -0.3(5) . . . . ? C11 C10 C13 C20 -93.0(3) . . . . ? C9 C10 C13 C20 84.0(3) . . . . ? C11 C10 C13 C22 32.6(4) . . . . ? C9 C10 C13 C22 -150.4(3) . . . . ? C21 O2 C17 O1 -6.4(5) . . . . ? C21 O2 C17 C16 173.6(3) . . . . ? N1 N2 C18 C20 0.0(3) . . . . ? N1 N2 C18 C19 178.7(3) . . . . ? N2 C18 C20 C21 0.0(3) . . . . ? C19 C18 C20 C21 -178.6(3) . . . . ? N2 C18 C20 C13 -178.1(3) . . . . ? C19 C18 C20 C13 3.3(5) . . . . ? C10 C13 C20 C21 69.7(4) . . . . ? C22 C13 C20 C21 -55.8(4) . . . . ? C10 C13 C20 C18 -112.7(3) . . . . ? C22 C13 C20 C18 121.9(3) . . . . ? N2 N1 C21 O2 179.7(2) . . . . ? C1 N1 C21 O2 7.4(5) . . . . ? N2 N1 C21 C20 0.1(3) . . . . ? C1 N1 C21 C20 -172.3(3) . . . . ? C17 O2 C21 N1 81.9(3) . . . . ? C17 O2 C21 C20 -98.5(4) . . . . ? C18 C20 C21 N1 -0.1(3) . . . . ? C13 C20 C21 N1 178.0(3) . . . . ? C18 C20 C21 O2 -179.7(3) . . . . ? C13 C20 C21 O2 -1.6(5) . . . . ? O4 N3 C22 C23 -111.2(4) . . . . ? O3 N3 C22 C23 68.3(4) . . . . ? O4 N3 C22 C13 125.0(4) . . . . ? O3 N3 C22 C13 -55.5(4) . . . . ? C20 C13 C22 N3 -47.1(4) . . . . ? C10 C13 C22 N3 -172.5(3) . . . . ? C20 C13 C22 C23 -167.2(3) . . . . ? C10 C13 C22 C23 67.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.647 _refine_diff_density_min -0.801 _refine_diff_density_rms 0.080