# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_zhangyan_II_6 #TrackingRef 'zhangyan-II-6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H15 N O' _chemical_formula_sum 'C17 H15 N O' _chemical_formula_weight 249.30 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 21/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 9.1485(6) _cell_length_b 13.8946(8) _cell_length_c 10.4647(7) _cell_angle_alpha 90.00 _cell_angle_beta 102.948(6) _cell_angle_gamma 90.00 _cell_volume 1296.40(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1327 _cell_measurement_theta_min 3.0457 _cell_measurement_theta_max 29.3656 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9652 _exptl_absorpt_correction_T_max 0.9690 _exptl_absorpt_process_details ; CrysAlis PRO (Agilent Technologies, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5082 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0376 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 25.35 _reflns_number_total 2372 _reflns_number_gt 1692 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'CrysAlis PRO (Agilent Technologies, 2011)' _computing_data_collection 'CrysAlis PRO' _computing_data_reduction 'CrysAlis PRO' _computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)' _computing_publication_material OLEX2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0398P)^2^+0.1650P] 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 0.0146(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2372 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0650 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1042 _refine_ls_wR_factor_gt 0.0902 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 0.67360(14) -0.02217(8) 0.97541(12) 0.0548(4) Uani 1 1 d . . . N1 N 0.54545(15) 0.11141(9) 0.89689(12) 0.0422(4) Uani 1 1 d . . . H1 H 0.4796 0.0975 0.9411 0.051 Uiso 1 1 calc R . . C1 C 0.8947(2) 0.01382(14) 0.83635(17) 0.0510(5) Uani 1 1 d . . . H1A H 0.8948 -0.0457 0.8771 0.061 Uiso 1 1 calc R . . C2 C 1.0061(2) 0.03574(17) 0.77229(19) 0.0632(6) Uani 1 1 d . . . H2 H 1.0816 -0.0086 0.7697 0.076 Uiso 1 1 calc R . . C3 C 1.0050(2) 0.12316(19) 0.71247(19) 0.0676(6) Uani 1 1 d . . . H3 H 1.0793 0.1377 0.6677 0.081 Uiso 1 1 calc R . . C4 C 0.8952(2) 0.19036(15) 0.71739(17) 0.0574(5) Uani 1 1 d . . . H4 H 0.8972 0.2497 0.6768 0.069 Uiso 1 1 calc R . . C5 C 0.78147(19) 0.17042(12) 0.78227(14) 0.0411(4) Uani 1 1 d . . . C6 C 0.78214(18) 0.07983(11) 0.84065(14) 0.0381(4) Uani 1 1 d . . . C7 C 0.66319(18) 0.05256(11) 0.90972(15) 0.0382(4) Uani 1 1 d . . . C8 C 0.51844(19) 0.19733(11) 0.81437(14) 0.0397(4) Uani 1 1 d . . . H8 H 0.4694 0.2445 0.8605 0.048 Uiso 1 1 calc R . . C9 C 0.6670(2) 0.24119(11) 0.80216(15) 0.0423(4) Uani 1 1 d . . . C10 C 0.7244(3) 0.32627(13) 0.8900(2) 0.0680(6) Uani 1 1 d . . . H10A H 0.6647 0.3479 0.9503 0.082 Uiso 1 1 calc R . . H10B H 0.8320 0.3325 0.9222 0.082 Uiso 1 1 calc R . . C11 C 0.6620(2) 0.34096(12) 0.74671(19) 0.0655(6) Uani 1 1 d . . . H11A H 0.7319 0.3564 0.6924 0.079 Uiso 1 1 calc R . . H11B H 0.5648 0.3718 0.7205 0.079 Uiso 1 1 calc R . . C12 C 0.41261(18) 0.17908(11) 0.68246(14) 0.0364(4) Uani 1 1 d . . . C13 C 0.32263(19) 0.25390(12) 0.62167(16) 0.0453(4) Uani 1 1 d . . . H13 H 0.3268 0.3130 0.6640 0.054 Uiso 1 1 calc R . . C14 C 0.2275(2) 0.24293(13) 0.50064(17) 0.0507(5) Uani 1 1 d . . . H14 H 0.1694 0.2944 0.4615 0.061 Uiso 1 1 calc R . . C15 C 0.2187(2) 0.15554(13) 0.43779(17) 0.0535(5) Uani 1 1 d . . . H15 H 0.1542 0.1475 0.3561 0.064 Uiso 1 1 calc R . . C16 C 0.3057(2) 0.08004(13) 0.49616(18) 0.0554(5) Uani 1 1 d . . . H16 H 0.2995 0.0208 0.4540 0.066 Uiso 1 1 calc R . . C17 C 0.4025(2) 0.09182(12) 0.61737(17) 0.0471(4) Uani 1 1 d . . . H17 H 0.4615 0.0404 0.6555 0.057 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 0.0540(8) 0.0462(7) 0.0672(8) 0.0207(6) 0.0197(6) 0.0063(6) N1 0.0441(9) 0.0444(8) 0.0423(7) 0.0124(6) 0.0189(6) 0.0058(7) C1 0.0438(11) 0.0560(11) 0.0521(10) -0.0071(9) 0.0083(8) -0.0008(9) C2 0.0407(12) 0.0863(16) 0.0636(12) -0.0141(12) 0.0135(9) 0.0008(11) C3 0.0411(12) 0.1069(18) 0.0587(12) -0.0108(13) 0.0197(9) -0.0192(12) C4 0.0542(13) 0.0718(13) 0.0464(10) 0.0039(10) 0.0120(9) -0.0232(11) C5 0.0417(10) 0.0488(10) 0.0305(8) -0.0038(8) 0.0034(7) -0.0137(8) C6 0.0363(9) 0.0426(9) 0.0349(8) -0.0047(7) 0.0069(7) -0.0037(7) C7 0.0405(10) 0.0361(9) 0.0380(9) 0.0019(8) 0.0086(7) -0.0010(7) C8 0.0486(11) 0.0342(8) 0.0390(9) 0.0029(7) 0.0153(8) 0.0052(8) C9 0.0517(11) 0.0357(9) 0.0370(9) 0.0015(7) 0.0046(8) -0.0085(8) C10 0.0807(16) 0.0466(11) 0.0662(13) -0.0114(10) -0.0056(11) -0.0106(10) C11 0.0735(15) 0.0438(11) 0.0700(13) 0.0122(9) -0.0030(11) -0.0163(10) C12 0.0357(9) 0.0346(9) 0.0418(9) 0.0041(7) 0.0151(7) -0.0011(7) C13 0.0503(11) 0.0369(9) 0.0486(10) 0.0028(8) 0.0108(8) 0.0013(8) C14 0.0485(12) 0.0490(11) 0.0522(11) 0.0113(9) 0.0064(9) 0.0029(8) C15 0.0520(12) 0.0622(13) 0.0440(10) 0.0025(9) 0.0057(8) -0.0077(10) C16 0.0611(13) 0.0477(11) 0.0557(11) -0.0095(9) 0.0097(9) -0.0043(9) C17 0.0486(11) 0.0386(10) 0.0547(10) 0.0012(8) 0.0130(8) 0.0025(8) _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 C7 1.2371(18) . ? N1 C7 1.335(2) . ? N1 C8 1.4617(19) . ? N1 H1 0.8600 . ? C1 C2 1.373(3) . ? C1 C6 1.387(2) . ? C1 H1A 0.9300 . ? C2 C3 1.365(3) . ? C2 H2 0.9300 . ? C3 C4 1.381(3) . ? C3 H3 0.9300 . ? C4 C5 1.391(2) . ? C4 H4 0.9300 . ? C5 C6 1.399(2) . ? C5 C9 1.485(2) . ? C6 C7 1.484(2) . ? C8 C12 1.519(2) . ? C8 C9 1.521(2) . ? C8 H8 0.9800 . ? C9 C11 1.499(2) . ? C9 C10 1.517(2) . ? C10 C11 1.494(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C17 1.384(2) . ? C12 C13 1.389(2) . ? C13 C14 1.375(2) . ? C13 H13 0.9300 . ? C14 C15 1.375(2) . ? C14 H14 0.9300 . ? C15 C16 1.375(2) . ? C15 H15 0.9300 . ? C16 C17 1.385(2) . ? C16 H16 0.9300 . ? C17 H17 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 C7 N1 C8 125.84(14) . . ? C7 N1 H1 117.1 . . ? C8 N1 H1 117.1 . . ? C2 C1 C6 120.43(18) . . ? C2 C1 H1A 119.8 . . ? C6 C1 H1A 119.8 . . ? C3 C2 C1 119.4(2) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C2 C3 C4 121.00(19) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C3 C4 C5 120.87(19) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C4 C5 C6 117.50(17) . . ? C4 C5 C9 124.35(16) . . ? C6 C5 C9 117.98(14) . . ? C1 C6 C5 120.76(16) . . ? C1 C6 C7 118.53(15) . . ? C5 C6 C7 120.70(15) . . ? O1 C7 N1 122.00(15) . . ? O1 C7 C6 120.75(15) . . ? N1 C7 C6 117.25(14) . . ? N1 C8 C12 112.92(13) . . ? N1 C8 C9 109.93(13) . . ? C12 C8 C9 112.96(12) . . ? N1 C8 H8 106.9 . . ? C12 C8 H8 106.9 . . ? C9 C8 H8 106.9 . . ? C5 C9 C11 121.30(16) . . ? C5 C9 C10 116.23(15) . . ? C11 C9 C10 59.37(11) . . ? C5 C9 C8 114.71(13) . . ? C11 C9 C8 116.90(16) . . ? C10 C9 C8 117.11(16) . . ? C11 C10 C9 59.73(11) . . ? C11 C10 H10A 117.8 . . ? C9 C10 H10A 117.8 . . ? C11 C10 H10B 117.8 . . ? C9 C10 H10B 117.8 . . ? H10A C10 H10B 114.9 . . ? C10 C11 C9 60.90(11) . . ? C10 C11 H11A 117.7 . . ? C9 C11 H11A 117.7 . . ? C10 C11 H11B 117.7 . . ? C9 C11 H11B 117.7 . . ? H11A C11 H11B 114.8 . . ? C17 C12 C13 117.60(15) . . ? C17 C12 C8 123.52(14) . . ? C13 C12 C8 118.87(13) . . ? C14 C13 C12 121.78(15) . . ? C14 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? C15 C14 C13 119.74(16) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C16 C15 C14 119.70(16) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C15 C16 C17 120.32(16) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? C12 C17 C16 120.87(16) . . ? C12 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.158 _refine_diff_density_min -0.136 _refine_diff_density_rms 0.032 _database_code_depnum_ccdc_archive 'CCDC 914986' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_zy_3_11_a #TrackingRef 'CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C19 H18 Cl N O), C H Cl3 ' _chemical_formula_sum 'C39 H37 Cl5 N2 O2' _chemical_formula_weight 742.96 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 monoclinic _symmetry_space_group_name_H-M 'P 21/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 23.2470(16) _cell_length_b 9.9836(7) _cell_length_c 16.0069(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.649(6) _cell_angle_gamma 90.00 _cell_volume 3714.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2665 _cell_measurement_theta_min 3.2558 _cell_measurement_theta_max 29.5391 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1544 _exptl_absorpt_coefficient_mu 0.427 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8755 _exptl_absorpt_correction_T_max 0.9082 _exptl_absorpt_process_details ; CrysAlis PRO (Agilent Technologies, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15156 _diffrn_reflns_av_R_equivalents 0.0396 _diffrn_reflns_av_sigmaI/netI 0.0548 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 25.35 _reflns_number_total 6772 _reflns_number_gt 3843 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'CrysAlis PRO (Agilent Technologies, 2011)' _computing_data_collection 'CrysAlis PRO' _computing_data_reduction 'CrysAlis PRO' _computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)' _computing_publication_material OLEX2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1189P)^2^+1.8702P] 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 6772 _refine_ls_number_parameters 440 _refine_ls_number_restraints 210 _refine_ls_R_factor_all 0.1281 _refine_ls_R_factor_gt 0.0757 _refine_ls_wR_factor_ref 0.2495 _refine_ls_wR_factor_gt 0.2056 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.066 _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 0.38913(6) 0.22642(17) 0.45151(7) 0.0862(5) Uani 1 1 d . . . Cl2 Cl 0.11564(8) 0.76811(19) 0.05981(10) 0.1110(6) Uani 1 1 d . . . Cl3 Cl 0.27027(8) 0.41188(19) 0.33523(10) 0.1102(6) Uani 1 1 d . . . Cl4 Cl 0.18786(7) 0.42925(19) 0.46598(11) 0.1099(6) Uani 1 1 d . . . Cl5 Cl 0.30223(10) 0.5346(2) 0.49000(14) 0.1337(7) Uani 1 1 d . . . O1 O 0.44577(12) -0.0464(2) 0.08019(16) 0.0526(7) Uani 1 1 d . . . O2 O 0.05456(12) 0.4649(3) 0.42119(18) 0.0597(8) Uani 1 1 d . . . N1 N 0.51598(14) 0.1106(3) 0.08578(19) 0.0441(8) Uani 1 1 d . . . H1 H 0.5315 0.0792 0.0414 0.053 Uiso 1 1 calc R . . N2 N -0.01315(16) 0.6271(3) 0.4196(3) 0.0643(10) Uani 1 1 d . . . H2 H -0.0285 0.5959 0.4642 0.077 Uiso 1 1 calc R . . C1 C 0.46999(16) 0.0488(3) 0.1163(2) 0.0413(9) Uani 1 1 d . . . C2 C 0.45012(16) 0.0975(3) 0.1990(2) 0.0406(9) Uani 1 1 d . . . C3 C 0.39563(17) 0.0593(4) 0.2267(3) 0.0493(10) Uani 1 1 d . . . H3 H 0.3725 0.0052 0.1930 0.059 Uiso 1 1 calc R . . C4 C 0.37581(18) 0.1013(4) 0.3036(3) 0.0548(11) Uani 1 1 d . . . H4 H 0.3394 0.0770 0.3217 0.066 Uiso 1 1 calc R . . C5 C 0.41154(18) 0.1806(4) 0.3529(2) 0.0514(10) Uani 1 1 d . . . C6 C 0.46526(17) 0.2205(4) 0.3265(2) 0.0447(9) Uani 1 1 d . . . H6 H 0.4881 0.2747 0.3605 0.054 Uiso 1 1 calc R . . C7 C 0.48491(16) 0.1792(3) 0.2490(2) 0.0387(8) Uani 1 1 d . . . C8 C 0.54427(16) 0.2163(4) 0.2179(2) 0.0417(9) Uani 1 1 d . . . H8 H 0.5544 0.3045 0.2407 0.050 Uiso 1 1 calc R . . C9 C 0.54075(17) 0.2280(3) 0.1242(2) 0.0435(9) Uani 1 1 d . . . C10 C 0.5279(2) 0.3608(4) 0.0839(3) 0.0592(11) Uani 1 1 d . . . H10A H 0.5242 0.4383 0.1201 0.071 Uiso 1 1 calc R . . H10B H 0.5030 0.3614 0.0349 0.071 Uiso 1 1 calc R . . C11 C 0.58671(19) 0.2981(4) 0.0761(3) 0.0562(11) Uani 1 1 d . . . H11A H 0.5971 0.2612 0.0223 0.067 Uiso 1 1 calc R . . H11B H 0.6183 0.3381 0.1074 0.067 Uiso 1 1 calc R . . C12 C 0.59097(17) 0.1158(4) 0.2459(2) 0.0467(9) Uani 1 1 d . . . H12A H 0.5800 0.0272 0.2265 0.056 Uiso 1 1 calc R . . H12B H 0.6268 0.1393 0.2190 0.056 Uiso 1 1 calc R . . C13 C 0.60141(18) 0.1098(4) 0.3398(2) 0.0529(10) Uani 1 1 d . . . H13A H 0.6080 0.1999 0.3605 0.064 Uiso 1 1 calc R . . H13B H 0.5672 0.0754 0.3664 0.064 Uiso 1 1 calc R . . C14 C 0.65216(16) 0.0229(4) 0.3642(2) 0.0465(9) Uani 1 1 d . . . C15 C 0.6995(2) 0.0734(5) 0.4056(3) 0.0727(14) Uani 1 1 d . . . H15 H 0.7001 0.1633 0.4208 0.087 Uiso 1 1 calc R . . C16 C 0.7464(2) -0.0071(7) 0.4253(4) 0.0881(17) Uani 1 1 d . . . H16 H 0.7783 0.0295 0.4526 0.106 Uiso 1 1 calc R . . C17 C 0.7460(2) -0.1393(6) 0.4049(3) 0.0748(14) Uani 1 1 d . . . H17 H 0.7774 -0.1933 0.4182 0.090 Uiso 1 1 calc R . . C18 C 0.7000(2) -0.1910(5) 0.3655(3) 0.0706(13) Uani 1 1 d . . . H18 H 0.6996 -0.2812 0.3510 0.085 Uiso 1 1 calc R . . C19 C 0.6532(2) -0.1112(4) 0.3461(3) 0.0591(11) Uani 1 1 d . . . H19 H 0.6214 -0.1498 0.3199 0.071 Uiso 1 1 calc R . . C20 C 0.03202(17) 0.5638(4) 0.3871(3) 0.0506(10) Uani 1 1 d . . . C21 C 0.05224(17) 0.6162(4) 0.3055(3) 0.0496(10) Uani 1 1 d . . . C22 C 0.10654(19) 0.5815(4) 0.2788(3) 0.0587(11) Uani 1 1 d . . . H22 H 0.1296 0.5261 0.3117 0.070 Uiso 1 1 calc R . . C23 C 0.1269(2) 0.6288(5) 0.2030(3) 0.0687(13) Uani 1 1 d . . . H23 H 0.1638 0.6075 0.1856 0.082 Uiso 1 1 calc R . . C24 C 0.0914(2) 0.7081(5) 0.1540(3) 0.0670(12) Uani 1 1 d . . . C25 C 0.0369(2) 0.7421(4) 0.1802(3) 0.0648(13) Uani 1 1 d . . . H25 H 0.0135 0.7951 0.1463 0.078 Uiso 1 1 calc R . . C26 C 0.01687(18) 0.6982(4) 0.2562(3) 0.0528(10) Uani 1 1 d . A . C27 C -0.0425(2) 0.7323(4) 0.2879(3) 0.0675(13) Uani 1 1 d . . . H27 H -0.0538 0.8192 0.2645 0.081 Uiso 0.680(13) 1 calc PR A 1 H27A H -0.0561 0.8162 0.2629 0.081 Uiso 0.320(13) 1 calc PR A 2 C28 C -0.0370(2) 0.7471(4) 0.3815(3) 0.0649(13) Uani 1 1 d . A . C29 C -0.0196(2) 0.8780(5) 0.4188(4) 0.0810(15) Uani 1 1 d . . . H29A H -0.0153 0.9537 0.3814 0.097 Uiso 1 1 calc R A . H29B H 0.0070 0.8765 0.4659 0.097 Uiso 1 1 calc R . . C30 C -0.0794(2) 0.8245(5) 0.4320(4) 0.0910(18) Uani 1 1 d . A . H30A H -0.0887 0.7907 0.4871 0.109 Uiso 1 1 calc R . . H30B H -0.1110 0.8679 0.4025 0.109 Uiso 1 1 calc R . . C31 C -0.0848(8) 0.6218(17) 0.2511(9) 0.1114(19) Uani 0.680(13) 1 d PU A 1 H31A H -0.0756 0.6081 0.1928 0.134 Uiso 0.680(13) 1 calc PR A 1 H31B H -0.0772 0.5382 0.2801 0.134 Uiso 0.680(13) 1 calc PR A 1 C32 C -0.1466(5) 0.6505(11) 0.2566(9) 0.1185(17) Uani 0.680(13) 1 d PU A 1 H32A H -0.1558 0.7284 0.2228 0.142 Uiso 0.680(13) 1 calc PR A 1 H32B H -0.1562 0.6708 0.3141 0.142 Uiso 0.680(13) 1 calc PR A 1 C33 C -0.1825(3) 0.5308(7) 0.2263(5) 0.1169(16) Uani 1 1 d U . . C34 C -0.1773(4) 0.4623(8) 0.1501(6) 0.1400(18) Uani 1 1 d U A . H34 H -0.1505 0.4904 0.1111 0.168 Uiso 1 1 calc R . . C35 C -0.2131(4) 0.3496(8) 0.1324(6) 0.1379(19) Uani 1 1 d U . . H35 H -0.2099 0.3025 0.0826 0.166 Uiso 1 1 calc R A . C36 C -0.2506(3) 0.3146(8) 0.1884(5) 0.1161(18) Uani 1 1 d U A . H36 H -0.2778 0.2490 0.1761 0.139 Uiso 1 1 calc R . . C37 C -0.2498(3) 0.3726(8) 0.2624(5) 0.1185(18) Uani 1 1 d U . . H37 H -0.2754 0.3432 0.3026 0.142 Uiso 1 1 calc R A . C38 C -0.2127(3) 0.4743(8) 0.2823(5) 0.1225(17) Uani 1 1 d U A . H38 H -0.2094 0.5028 0.3374 0.147 Uiso 1 1 calc R . . C39 C 0.2606(2) 0.4109(6) 0.4426(3) 0.0783(15) Uani 1 1 d . . . H39 H 0.2735 0.3239 0.4641 0.094 Uiso 1 1 calc R . . C32A C -0.1216(11) 0.632(3) 0.205(2) 0.1185(17) Uani 0.320(13) 1 d PU A 2 H32C H -0.1007 0.5979 0.1571 0.142 Uiso 0.320(13) 1 calc PR A 2 H32D H -0.1328 0.7240 0.1937 0.142 Uiso 0.320(13) 1 calc PR A 2 C31A C -0.0883(17) 0.623(4) 0.2781(19) 0.1114(19) Uani 0.320(13) 1 d PU A 2 H31C H -0.0694 0.5363 0.2792 0.134 Uiso 0.320(13) 1 calc PR A 2 H31D H -0.1138 0.6269 0.3256 0.134 Uiso 0.320(13) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0643(8) 0.1417(13) 0.0529(7) -0.0109(7) 0.0109(6) 0.0310(8) Cl2 0.1285(14) 0.1317(14) 0.0731(10) 0.0296(9) 0.0167(9) -0.0076(11) Cl3 0.1132(13) 0.1482(15) 0.0696(9) 0.0044(9) 0.0162(9) 0.0051(11) Cl4 0.0728(9) 0.1553(15) 0.1019(12) 0.0308(10) 0.0190(8) 0.0358(10) Cl5 0.1388(17) 0.1306(15) 0.1312(16) -0.0276(12) -0.0188(13) -0.0223(13) O1 0.0637(18) 0.0441(15) 0.0498(16) -0.0084(13) -0.0065(13) -0.0115(14) O2 0.0582(18) 0.0531(16) 0.0678(19) 0.0123(15) 0.0003(14) 0.0125(15) N1 0.055(2) 0.0411(17) 0.0358(16) -0.0091(13) -0.0005(14) -0.0057(15) N2 0.058(2) 0.054(2) 0.082(3) 0.0182(19) 0.015(2) 0.0084(18) C1 0.050(2) 0.0326(18) 0.041(2) 0.0002(16) -0.0076(17) 0.0018(18) C2 0.048(2) 0.0331(18) 0.041(2) 0.0036(16) -0.0051(17) 0.0016(16) C3 0.047(2) 0.042(2) 0.059(3) 0.0042(19) -0.0083(19) 0.0004(18) C4 0.042(2) 0.061(3) 0.061(3) 0.010(2) 0.006(2) 0.009(2) C5 0.054(2) 0.058(2) 0.042(2) 0.0032(19) 0.0054(19) 0.022(2) C6 0.052(2) 0.044(2) 0.038(2) -0.0030(17) -0.0047(17) 0.0114(18) C7 0.044(2) 0.0304(18) 0.041(2) -0.0001(16) -0.0037(16) 0.0035(16) C8 0.048(2) 0.0364(19) 0.041(2) -0.0071(16) -0.0031(17) -0.0024(17) C9 0.051(2) 0.0397(19) 0.040(2) -0.0022(16) -0.0054(17) -0.0070(17) C10 0.075(3) 0.047(2) 0.055(3) 0.010(2) -0.010(2) -0.005(2) C11 0.059(3) 0.061(3) 0.049(2) -0.001(2) 0.004(2) -0.015(2) C12 0.048(2) 0.054(2) 0.038(2) -0.0015(17) -0.0029(17) 0.0045(19) C13 0.059(3) 0.059(2) 0.041(2) -0.0047(19) -0.0010(19) 0.003(2) C14 0.049(2) 0.059(2) 0.0319(19) 0.0016(18) -0.0003(16) -0.0046(19) C15 0.073(3) 0.069(3) 0.076(3) -0.006(3) -0.019(3) -0.009(3) C16 0.054(3) 0.118(5) 0.092(4) 0.007(4) -0.024(3) -0.015(3) C17 0.059(3) 0.098(4) 0.068(3) 0.013(3) -0.002(2) 0.015(3) C18 0.072(3) 0.071(3) 0.068(3) 0.007(3) -0.008(3) 0.015(3) C19 0.062(3) 0.062(3) 0.053(3) 0.001(2) -0.012(2) 0.002(2) C20 0.042(2) 0.041(2) 0.068(3) 0.000(2) -0.004(2) -0.0016(18) C21 0.051(2) 0.039(2) 0.058(3) -0.0021(18) -0.008(2) -0.0050(19) C22 0.056(3) 0.059(3) 0.062(3) 0.002(2) -0.006(2) 0.002(2) C23 0.064(3) 0.074(3) 0.068(3) -0.001(3) 0.003(2) -0.003(3) C24 0.075(3) 0.065(3) 0.061(3) 0.002(2) 0.000(2) -0.009(3) C25 0.082(4) 0.051(3) 0.060(3) 0.009(2) -0.017(3) -0.009(2) C26 0.052(2) 0.039(2) 0.067(3) 0.003(2) -0.012(2) -0.0051(19) C27 0.054(3) 0.052(3) 0.096(4) 0.017(2) -0.008(3) 0.003(2) C28 0.054(3) 0.046(2) 0.095(4) 0.013(2) 0.012(3) 0.011(2) C29 0.086(4) 0.054(3) 0.102(4) 0.000(3) 0.011(3) 0.005(3) C30 0.080(4) 0.074(3) 0.119(5) 0.018(3) 0.028(3) 0.028(3) C31 0.084(3) 0.125(3) 0.125(4) 0.005(4) -0.022(4) -0.025(3) C32 0.097(3) 0.131(3) 0.128(4) 0.001(3) -0.016(3) -0.027(3) C33 0.105(3) 0.120(3) 0.125(4) 0.000(3) -0.026(3) -0.032(3) C34 0.131(3) 0.155(4) 0.134(4) 0.015(3) -0.007(3) -0.048(3) C35 0.134(4) 0.154(4) 0.126(4) -0.006(4) -0.022(3) -0.050(4) C36 0.093(4) 0.127(4) 0.127(4) 0.003(4) -0.019(3) -0.036(3) C37 0.091(3) 0.132(4) 0.132(4) 0.004(3) -0.004(3) -0.019(3) C38 0.107(3) 0.131(3) 0.129(4) -0.006(3) -0.012(3) -0.018(3) C39 0.069(3) 0.095(4) 0.071(3) 0.010(3) 0.002(3) 0.020(3) C32A 0.097(3) 0.131(3) 0.128(4) 0.001(3) -0.016(3) -0.027(3) C31A 0.084(3) 0.125(3) 0.125(4) 0.005(4) -0.022(4) -0.025(3) _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 C5 1.729(4) . ? Cl2 C24 1.723(5) . ? Cl3 C39 1.735(5) . ? Cl4 C39 1.746(5) . ? Cl5 C39 1.738(6) . ? O1 C1 1.244(4) . ? O2 C20 1.241(5) . ? N1 C1 1.332(5) . ? N1 C9 1.440(4) . ? N1 H1 0.8600 . ? N2 C20 1.336(5) . ? N2 C28 1.452(5) . ? N2 H2 0.8600 . ? C1 C2 1.489(5) . ? C2 C7 1.395(5) . ? C2 C3 1.400(5) . ? C3 C4 1.384(6) . ? C3 H3 0.9300 . ? C4 C5 1.387(6) . ? C4 H4 0.9300 . ? C5 C6 1.381(6) . ? C6 C7 1.390(5) . ? C6 H6 0.9300 . ? C7 C8 1.518(5) . ? C8 C9 1.507(5) . ? C8 C12 1.541(5) . ? C8 H8 0.9800 . ? C9 C11 1.497(5) . ? C9 C10 1.503(5) . ? C10 C11 1.511(6) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.521(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.512(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C19 1.370(6) . ? C14 C15 1.375(6) . ? C15 C16 1.389(7) . ? C15 H15 0.9300 . ? C16 C17 1.359(8) . ? C16 H16 0.9300 . ? C17 C18 1.339(7) . ? C17 H17 0.9300 . ? C18 C19 1.380(6) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.488(6) . ? C21 C22 1.381(6) . ? C21 C26 1.397(6) . ? C22 C23 1.389(6) . ? C22 H22 0.9300 . ? C23 C24 1.380(7) . ? C23 H23 0.9300 . ? C24 C25 1.382(7) . ? C25 C26 1.379(6) . ? C25 H25 0.9300 . ? C26 C27 1.515(6) . ? C27 C28 1.509(7) . ? C27 C31A 1.53(4) . ? C27 C31 1.587(17) . ? C27 H27 0.9800 . ? C27 H27A 0.9800 . ? C28 C29 1.490(7) . ? C28 C30 1.498(7) . ? C29 C30 1.507(7) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.47(2) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 C33 1.533(12) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 C38 1.276(10) . ? C33 C34 1.405(11) . ? C33 C32A 1.78(2) . ? C34 C35 1.426(10) . ? C34 H34 0.9300 . ? C35 C36 1.303(10) . ? C35 H35 0.9300 . ? C36 C37 1.319(10) . ? C36 H36 0.9300 . ? C37 C38 1.366(9) . ? C37 H37 0.9300 . ? C38 H38 0.9300 . ? C39 H39 0.9800 . ? C32A C31A 1.40(4) . ? C32A H32C 0.9700 . ? C32A H32D 0.9700 . ? C31A H31C 0.9700 . ? C31A H31D 0.9700 . ? 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 C1 N1 C9 122.6(3) . . ? C1 N1 H1 118.7 . . ? C9 N1 H1 118.7 . . ? C20 N2 C28 121.6(4) . . ? C20 N2 H2 119.2 . . ? C28 N2 H2 119.2 . . ? O1 C1 N1 123.0(3) . . ? O1 C1 C2 121.3(3) . . ? N1 C1 C2 115.7(3) . . ? C7 C2 C3 119.9(4) . . ? C7 C2 C1 121.2(3) . . ? C3 C2 C1 118.9(3) . . ? C4 C3 C2 120.7(4) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 118.4(4) . . ? C3 C4 H4 120.8 . . ? C5 C4 H4 120.8 . . ? C6 C5 C4 121.9(4) . . ? C6 C5 Cl1 119.0(3) . . ? C4 C5 Cl1 119.1(3) . . ? C5 C6 C7 119.7(4) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C6 C7 C2 119.4(3) . . ? C6 C7 C8 122.0(3) . . ? C2 C7 C8 118.6(3) . . ? C9 C8 C7 107.8(3) . . ? C9 C8 C12 111.7(3) . . ? C7 C8 C12 112.7(3) . . ? C9 C8 H8 108.2 . . ? C7 C8 H8 108.2 . . ? C12 C8 H8 108.2 . . ? N1 C9 C11 116.4(3) . . ? N1 C9 C10 117.3(3) . . ? C11 C9 C10 60.5(3) . . ? N1 C9 C8 112.3(3) . . ? C11 C9 C8 121.1(3) . . ? C10 C9 C8 120.2(3) . . ? C9 C10 C11 59.6(3) . . ? C9 C10 H10A 117.8 . . ? C11 C10 H10A 117.8 . . ? C9 C10 H10B 117.8 . . ? C11 C10 H10B 117.8 . . ? H10A C10 H10B 115.0 . . ? C9 C11 C10 59.9(3) . . ? C9 C11 H11A 117.8 . . ? C10 C11 H11A 117.8 . . ? C9 C11 H11B 117.8 . . ? C10 C11 H11B 117.8 . . ? H11A C11 H11B 114.9 . . ? C13 C12 C8 114.6(3) . . ? C13 C12 H12A 108.6 . . ? C8 C12 H12A 108.6 . . ? C13 C12 H12B 108.6 . . ? C8 C12 H12B 108.6 . . ? H12A C12 H12B 107.6 . . ? C14 C13 C12 113.1(3) . . ? C14 C13 H13A 109.0 . . ? C12 C13 H13A 109.0 . . ? C14 C13 H13B 109.0 . . ? C12 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C19 C14 C15 116.4(4) . . ? C19 C14 C13 121.5(4) . . ? C15 C14 C13 122.1(4) . . ? C14 C15 C16 121.3(5) . . ? C14 C15 H15 119.4 . . ? C16 C15 H15 119.4 . . ? C17 C16 C15 120.3(5) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C18 C17 C16 119.4(5) . . ? C18 C17 H17 120.3 . . ? C16 C17 H17 120.3 . . ? C17 C18 C19 120.5(5) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C14 C19 C18 122.2(4) . . ? C14 C19 H19 118.9 . . ? C18 C19 H19 118.9 . . ? O2 C20 N2 122.3(4) . . ? O2 C20 C21 122.0(4) . . ? N2 C20 C21 115.7(4) . . ? C22 C21 C26 120.4(4) . . ? C22 C21 C20 118.8(4) . . ? C26 C21 C20 120.8(4) . . ? C21 C22 C23 120.4(4) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C24 C23 C22 118.9(5) . . ? C24 C23 H23 120.5 . . ? C22 C23 H23 120.5 . . ? C23 C24 C25 120.8(5) . . ? C23 C24 Cl2 119.8(4) . . ? C25 C24 Cl2 119.3(4) . . ? C26 C25 C24 120.6(4) . . ? C26 C25 H25 119.7 . . ? C24 C25 H25 119.7 . . ? C25 C26 C21 118.8(4) . . ? C25 C26 C27 122.8(4) . . ? C21 C26 C27 118.4(4) . . ? C28 C27 C26 106.7(4) . . ? C28 C27 C31A 102.9(12) . . ? C26 C27 C31A 116.1(15) . . ? C28 C27 C31 118.8(6) . . ? C26 C27 C31 106.4(7) . . ? C31A C27 C31 16.1(14) . . ? C28 C27 H27 108.2 . . ? C26 C27 H27 108.2 . . ? C31A C27 H27 114.1 . . ? C31 C27 H27 108.2 . . ? C28 C27 H27A 110.2 . . ? C26 C27 H27A 110.2 . . ? C31A C27 H27A 110.2 . . ? C31 C27 H27A 104.3 . . ? H27 C27 H27A 3.9 . . ? N2 C28 C29 117.1(4) . . ? N2 C28 C30 116.7(4) . . ? C29 C28 C30 60.6(3) . . ? N2 C28 C27 111.3(4) . . ? C29 C28 C27 120.2(4) . . ? C30 C28 C27 122.5(4) . . ? C28 C29 C30 60.0(3) . . ? C28 C29 H29A 117.8 . . ? C30 C29 H29A 117.8 . . ? C28 C29 H29B 117.8 . . ? C30 C29 H29B 117.8 . . ? H29A C29 H29B 114.9 . . ? C28 C30 C29 59.5(3) . . ? C28 C30 H30A 117.8 . . ? C29 C30 H30A 117.8 . . ? C28 C30 H30B 117.8 . . ? C29 C30 H30B 117.8 . . ? H30A C30 H30B 115.0 . . ? C32 C31 C27 116.4(12) . . ? C32 C31 H31A 108.2 . . ? C27 C31 H31A 108.2 . . ? C32 C31 H31B 108.2 . . ? C27 C31 H31B 108.2 . . ? H31A C31 H31B 107.3 . . ? C31 C32 C33 111.0(11) . . ? C31 C32 H32A 109.4 . . ? C33 C32 H32A 109.4 . . ? C31 C32 H32B 109.4 . . ? C33 C32 H32B 109.4 . . ? H32A C32 H32B 108.0 . . ? C38 C33 C34 116.6(7) . . ? C38 C33 C32 115.1(9) . . ? C34 C33 C32 127.0(9) . . ? C38 C33 C32A 146.5(12) . . ? C34 C33 C32A 91.8(12) . . ? C32 C33 C32A 35.5(9) . . ? C33 C34 C35 120.0(8) . . ? C33 C34 H34 120.0 . . ? C35 C34 H34 120.0 . . ? C36 C35 C34 117.9(8) . . ? C36 C35 H35 121.0 . . ? C34 C35 H35 121.0 . . ? C35 C36 C37 119.8(7) . . ? C35 C36 H36 120.1 . . ? C37 C36 H36 120.1 . . ? C36 C37 C38 122.5(8) . . ? C36 C37 H37 118.7 . . ? C38 C37 H37 118.7 . . ? C33 C38 C37 121.0(8) . . ? C33 C38 H38 119.5 . . ? C37 C38 H38 119.5 . . ? Cl3 C39 Cl5 110.6(3) . . ? Cl3 C39 Cl4 110.4(3) . . ? Cl5 C39 Cl4 111.6(3) . . ? Cl3 C39 H39 108.1 . . ? Cl5 C39 H39 108.1 . . ? Cl4 C39 H39 108.1 . . ? C31A C32A C33 104(2) . . ? C31A C32A H32C 111.1 . . ? C33 C32A H32C 111.1 . . ? C31A C32A H32D 111.1 . . ? C33 C32A H32D 111.1 . . ? H32C C32A H32D 109.0 . . ? C32A C31A C27 115(2) . . ? C32A C31A H31C 108.6 . . ? C27 C31A H31C 108.6 . . ? C32A C31A H31D 108.6 . . ? C27 C31A H31D 108.6 . . ? H31C C31A H31D 107.6 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.622 _refine_diff_density_min -0.676 _refine_diff_density_rms 0.057 _database_code_depnum_ccdc_archive 'CCDC 921701' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_130226_Zy_3_32 #TrackingRef 'CIF.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 N O2, C H Cl3 ' _chemical_formula_sum 'C16 H14 Cl3 N O2' _chemical_formula_weight 358.63 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 orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 9.7761(9) _cell_length_b 14.7382(10) _cell_length_c 24.0669(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3467.6(5) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3926 _cell_measurement_theta_min 3.0135 _cell_measurement_theta_max 29.4786 _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 0.533 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7839 _exptl_absorpt_correction_T_max 0.9008 _exptl_absorpt_process_details ; CrysAlis PRO (Agilent Technologies, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21630 _diffrn_reflns_av_R_equivalents 0.0532 _diffrn_reflns_av_sigmaI/netI 0.0262 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3167 _reflns_number_gt 2184 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'CrysAlis PRO (Agilent Technologies, 2011)' _computing_data_collection 'CrysAlis PRO' _computing_data_reduction 'CrysAlis PRO' _computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)' _computing_publication_material OLEX2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1446P)^2^+5.5871P] 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 3167 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1182 _refine_ls_R_factor_gt 0.0901 _refine_ls_wR_factor_ref 0.2826 _refine_ls_wR_factor_gt 0.2524 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 -0.1833(2) 0.12688(14) 0.31642(9) 0.1128(7) Uani 1 1 d . . . Cl2 Cl 0.1060(2) 0.13064(14) 0.32865(10) 0.1211(8) Uani 1 1 d . . . Cl3 Cl -0.0151(4) -0.00016(14) 0.25512(8) 0.1517(12) Uani 1 1 d . . . O1 O 0.5459(3) 0.3355(2) 0.35801(12) 0.0586(9) Uani 1 1 d . . . O2 O 0.5440(3) 0.4623(2) 0.43292(12) 0.0569(8) Uani 1 1 d . . . N1 N 0.4540(4) 0.3763(3) 0.50052(14) 0.0540(9) Uani 1 1 d . . . H1 H 0.4567 0.4239 0.5212 0.065 Uiso 1 1 calc R . . C1 C 0.5264(6) 0.2628(4) 0.3246(2) 0.0673(14) Uani 1 1 d . . . H1A H 0.5529 0.2603 0.2875 0.081 Uiso 1 1 calc R . . C2 C 0.4646(5) 0.1954(3) 0.35139(19) 0.0604(12) Uani 1 1 d . . . H2 H 0.4418 0.1390 0.3368 0.072 Uiso 1 1 calc R . . C3 C 0.4398(4) 0.2261(3) 0.40676(17) 0.0473(10) Uani 1 1 d . . . C4 C 0.4897(4) 0.3129(3) 0.40862(16) 0.0446(9) Uani 1 1 d . . . C5 C 0.4973(4) 0.3875(3) 0.44846(16) 0.0449(9) Uani 1 1 d . . . C6 C 0.4023(6) 0.2938(3) 0.52730(18) 0.0627(12) Uani 1 1 d . . . H6A H 0.3615 0.3103 0.5626 0.075 Uiso 1 1 calc R . . H6B H 0.4792 0.2541 0.5351 0.075 Uiso 1 1 calc R . . C7 C 0.2974(5) 0.2410(3) 0.49358(19) 0.0618(12) Uani 1 1 d . . . H7A H 0.2423 0.2047 0.5186 0.074 Uiso 1 1 calc R . . H7B H 0.2370 0.2836 0.4750 0.074 Uiso 1 1 calc R . . C8 C 0.3612(4) 0.1800(3) 0.45086(18) 0.0523(10) Uani 1 1 d . . . C9 C 0.3444(5) 0.0898(3) 0.4539(2) 0.0611(12) Uani 1 1 d . . . H9 H 0.2826 0.0700 0.4806 0.073 Uiso 1 1 calc R . . C10 C 0.4099(5) 0.0175(3) 0.4208(2) 0.0573(11) Uani 1 1 d . . . C11 C 0.3317(6) -0.0492(3) 0.3958(2) 0.0707(14) Uani 1 1 d . . . H11 H 0.2370 -0.0467 0.3991 0.085 Uiso 1 1 calc R . . C12 C 0.3898(7) -0.1189(4) 0.3661(3) 0.0828(17) Uani 1 1 d . . . H12 H 0.3348 -0.1618 0.3487 0.099 Uiso 1 1 calc R . . C13 C 0.5306(7) -0.1249(4) 0.3624(3) 0.0833(18) Uani 1 1 d . . . H13 H 0.5712 -0.1728 0.3434 0.100 Uiso 1 1 calc R . . C14 C 0.6103(6) -0.0593(4) 0.3871(3) 0.0777(15) Uani 1 1 d . . . H14 H 0.7050 -0.0625 0.3842 0.093 Uiso 1 1 calc R . . C15 C 0.5510(5) 0.0108(4) 0.4158(2) 0.0712(14) Uani 1 1 d . . . H15 H 0.6062 0.0546 0.4322 0.085 Uiso 1 1 calc R . . C16 C -0.0352(6) 0.0574(4) 0.3166(2) 0.0755(16) Uani 1 1 d . . . H16 H -0.0418 0.0137 0.3471 0.091 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 0.0875(13) 0.1177(15) 0.1332(16) 0.0030(11) -0.0226(10) 0.0057(10) Cl2 0.0877(13) 0.1000(14) 0.176(2) -0.0038(12) -0.0165(12) -0.0060(10) Cl3 0.302(4) 0.0830(13) 0.0705(11) -0.0050(9) 0.0202(14) 0.0058(16) O1 0.080(2) 0.0471(17) 0.0489(16) 0.0004(13) 0.0127(14) -0.0044(15) O2 0.073(2) 0.0454(17) 0.0522(17) -0.0017(14) 0.0049(14) -0.0089(14) N1 0.065(2) 0.049(2) 0.048(2) -0.0019(16) 0.0048(17) -0.0057(17) C1 0.090(4) 0.058(3) 0.054(3) -0.008(2) 0.010(2) 0.001(3) C2 0.079(3) 0.045(3) 0.057(3) -0.008(2) -0.001(2) -0.001(2) C3 0.045(2) 0.044(2) 0.053(2) 0.0012(18) -0.0027(18) 0.0026(17) C4 0.046(2) 0.044(2) 0.044(2) 0.0034(17) 0.0005(16) 0.0042(17) C5 0.043(2) 0.045(2) 0.047(2) 0.0016(17) -0.0045(17) -0.0007(17) C6 0.082(3) 0.058(3) 0.049(2) 0.003(2) 0.012(2) -0.002(2) C7 0.054(3) 0.059(3) 0.073(3) 0.001(2) 0.016(2) -0.007(2) C8 0.044(2) 0.050(2) 0.064(3) 0.003(2) 0.0015(19) -0.0036(18) C9 0.057(3) 0.054(3) 0.072(3) 0.004(2) 0.008(2) -0.011(2) C10 0.055(3) 0.044(2) 0.072(3) 0.011(2) 0.006(2) -0.006(2) C11 0.062(3) 0.051(3) 0.099(4) 0.003(3) 0.011(3) -0.013(2) C12 0.096(5) 0.052(3) 0.101(4) -0.006(3) 0.005(3) -0.012(3) C13 0.110(5) 0.054(3) 0.085(4) 0.010(3) 0.024(3) 0.019(3) C14 0.059(3) 0.072(4) 0.102(4) 0.019(3) 0.005(3) 0.014(3) C15 0.057(3) 0.061(3) 0.096(4) 0.008(3) -0.007(3) -0.003(2) C16 0.101(5) 0.066(3) 0.059(3) 0.008(2) 0.000(3) -0.001(3) _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 C16 1.773(6) . ? Cl2 C16 1.776(6) . ? Cl3 C16 1.716(6) . ? O1 C1 1.352(6) . ? O1 C4 1.377(5) . ? O2 C5 1.251(5) . ? N1 C5 1.333(5) . ? N1 C6 1.467(6) . ? N1 H1 0.8600 . ? C1 C2 1.329(7) . ? C1 H1A 0.9300 . ? C2 C3 1.428(6) . ? C2 H2 0.9300 . ? C3 C4 1.370(6) . ? C3 C8 1.476(6) . ? C4 C5 1.461(6) . ? C6 C7 1.522(7) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.502(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.342(6) . ? C9 C10 1.476(7) . ? C9 H9 0.9300 . ? C10 C11 1.383(7) . ? C10 C15 1.388(7) . ? C11 C12 1.375(8) . ? C11 H11 0.9300 . ? C12 C13 1.382(9) . ? C12 H12 0.9300 . ? C13 C14 1.376(9) . ? C13 H13 0.9300 . ? C14 C15 1.371(8) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 H16 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 C1 O1 C4 106.1(4) . . ? C5 N1 C6 128.7(4) . . ? C5 N1 H1 115.7 . . ? C6 N1 H1 115.7 . . ? C2 C1 O1 111.6(4) . . ? C2 C1 H1A 124.2 . . ? O1 C1 H1A 124.2 . . ? C1 C2 C3 107.0(4) . . ? C1 C2 H2 126.5 . . ? C3 C2 H2 126.5 . . ? C4 C3 C2 105.4(4) . . ? C4 C3 C8 126.3(4) . . ? C2 C3 C8 127.8(4) . . ? C3 C4 O1 109.8(3) . . ? C3 C4 C5 137.9(4) . . ? O1 C4 C5 112.2(4) . . ? O2 C5 N1 120.4(4) . . ? O2 C5 C4 119.1(4) . . ? N1 C5 C4 120.5(4) . . ? N1 C6 C7 114.9(4) . . ? N1 C6 H6A 108.5 . . ? C7 C6 H6A 108.5 . . ? N1 C6 H6B 108.5 . . ? C7 C6 H6B 108.5 . . ? H6A C6 H6B 107.5 . . ? C8 C7 C6 113.0(4) . . ? C8 C7 H7A 109.0 . . ? C6 C7 H7A 109.0 . . ? C8 C7 H7B 109.0 . . ? C6 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C9 C8 C3 124.0(4) . . ? C9 C8 C7 120.4(4) . . ? C3 C8 C7 115.6(4) . . ? C8 C9 C10 129.3(4) . . ? C8 C9 H9 115.3 . . ? C10 C9 H9 115.3 . . ? C11 C10 C15 117.4(5) . . ? C11 C10 C9 120.5(4) . . ? C15 C10 C9 122.0(4) . . ? C12 C11 C10 121.9(5) . . ? C12 C11 H11 119.0 . . ? C10 C11 H11 119.0 . . ? C11 C12 C13 119.5(6) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C14 C13 C12 119.4(5) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C15 C14 C13 120.5(5) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C10 121.2(5) . . ? C14 C15 H15 119.4 . . ? C10 C15 H15 119.4 . . ? Cl3 C16 Cl1 112.2(3) . . ? Cl3 C16 Cl2 110.7(3) . . ? Cl1 C16 Cl2 106.5(3) . . ? Cl3 C16 H16 109.1 . . ? Cl1 C16 H16 109.1 . . ? Cl2 C16 H16 109.1 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.856 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.083 _database_code_depnum_ccdc_archive 'CCDC 927437'