# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_author_name 'Xihe Bi' _publ_contact_author_name 'Xihe Bi' _publ_contact_author_email drxhbi@gmail.com data_091125-lq01-gj _database_code_depnum_ccdc_archive 'CCDC 792079' #TrackingRef '091125-lq01-gj.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H17 Cl N2 O' _chemical_formula_sum 'C19 H17 Cl N2 O' _chemical_formula_weight 324.80 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 '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 16.137(5) _cell_length_b 10.330(5) _cell_length_c 20.677(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 97.444(5) _cell_angle_gamma 90.000(5) _cell_volume 3418(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6026 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 67.84 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 2.015 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.625 _exptl_absorpt_correction_T_max 0.851 _exptl_absorpt_process_details ; CrysAlis (Oxford Diffraction, 2006) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini R Ultra' _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean 10.0 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22036 _diffrn_reflns_av_R_equivalents 0.0943 _diffrn_reflns_av_sigmaI/netI 0.0763 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 4.31 _diffrn_reflns_theta_max 67.84 _reflns_number_total 6026 _reflns_number_gt 2655 _reflns_threshold_expression >2\s(I) _computing_data_collection 'CrysAlis (Oxford Diffraction, 2006)' _computing_cell_refinement CrysAlis _computing_data_reduction CrysAlis _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.1075P)^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 6026 _refine_ls_number_parameters 423 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1401 _refine_ls_R_factor_gt 0.0696 _refine_ls_wR_factor_ref 0.1976 _refine_ls_wR_factor_gt 0.1624 _refine_ls_goodness_of_fit_ref 0.852 _refine_ls_restrained_S_all 0.852 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl2 Cl 1.44252(8) -0.21349(18) 0.58916(7) 0.1244(6) Uani 1 1 d . . . Cl1 Cl 0.59726(10) 0.60135(12) 0.71496(9) 0.1252(6) Uani 1 1 d . . . O1 O 0.8262(2) -0.2501(3) 0.80017(13) 0.0830(8) Uani 1 1 d . . . O2 O 0.85537(18) -0.3386(3) 0.54210(14) 0.0877(9) Uani 1 1 d . . . N1 N 0.6997(2) 0.0560(3) 0.69151(14) 0.0645(8) Uani 1 1 d . . . N2 N 0.8270(2) -0.3398(3) 0.69991(18) 0.0676(9) Uani 1 1 d . . . N4 N 0.8024(2) -0.2829(3) 0.43869(17) 0.0682(9) Uani 1 1 d . . . N3 N 1.0832(2) -0.2039(3) 0.48501(15) 0.0661(8) Uani 1 1 d . . . C26 C 1.0229(2) -0.2747(4) 0.51027(18) 0.0626(9) Uani 1 1 d . . . C13 C 0.8067(3) -0.2436(4) 0.7408(2) 0.0670(10) Uani 1 1 d . . . C10 C 0.7091(3) -0.1352(4) 0.64768(18) 0.0721(11) Uani 1 1 d . . . H10 H 0.7025 -0.2046 0.6188 0.087 Uiso 1 1 calc R . . C30 C 0.9630(3) -0.1514(4) 0.42758(19) 0.0694(10) Uani 1 1 d . . . H30 H 0.9231 -0.1149 0.3965 0.083 Uiso 1 1 calc R . . C33 C 0.7169(2) -0.3070(4) 0.4397(2) 0.0682(10) Uani 1 1 d . . . C31 C 0.9472(2) -0.2431(4) 0.47492(17) 0.0612(9) Uani 1 1 d . . . C23 C 1.1701(2) -0.2054(4) 0.51005(19) 0.0667(10) Uani 1 1 d . . . C25 C 1.3007(3) -0.3184(5) 0.5313(2) 0.0825(12) Uani 1 1 d . . . H25 H 1.3320 -0.3935 0.5292 0.099 Uiso 1 1 calc R . . C28 C 1.0463(3) -0.1250(4) 0.4348(2) 0.0721(11) Uani 1 1 d . . . C5 C 0.7023(3) 0.2812(4) 0.6588(2) 0.0744(11) Uani 1 1 d . . . H5 H 0.7365 0.2579 0.6278 0.089 Uiso 1 1 calc R . . C11 C 0.6723(3) -0.0175(4) 0.63697(18) 0.0705(11) Uani 1 1 d . . . C24 C 1.2170(3) -0.3162(4) 0.5053(2) 0.0746(11) Uani 1 1 d . . . H24 H 1.1925 -0.3892 0.4846 0.090 Uiso 1 1 calc R . . C22 C 1.2080(3) -0.0977(4) 0.5398(2) 0.0856(13) Uani 1 1 d . . . H22 H 1.1770 -0.0228 0.5434 0.103 Uiso 1 1 calc R . . C32 C 0.8660(2) -0.2926(4) 0.48891(18) 0.0629(9) Uani 1 1 d . . . C14 C 0.8674(2) -0.4566(3) 0.71911(17) 0.0612(9) Uani 1 1 d . . . C3 C 0.6263(3) 0.2232(4) 0.7446(2) 0.0786(12) Uani 1 1 d . . . H3 H 0.6074 0.1608 0.7716 0.094 Uiso 1 1 calc R . . C27 C 1.0430(3) -0.3676(5) 0.5651(2) 0.0873(13) Uani 1 1 d . . . H27A H 1.1021 -0.3669 0.5790 0.131 Uiso 1 1 calc R . . H27B H 1.0260 -0.4531 0.5507 0.131 Uiso 1 1 calc R . . H27C H 1.0139 -0.3428 0.6008 0.131 Uiso 1 1 calc R . . C7 C 0.7518(3) -0.0146(4) 0.73618(18) 0.0659(10) Uani 1 1 d . . . C4 C 0.6769(2) 0.1882(4) 0.69893(18) 0.0634(10) Uani 1 1 d . . . C1 C 0.6284(3) 0.4422(4) 0.7090(2) 0.0793(12) Uani 1 1 d . . . C6 C 0.6785(3) 0.4078(4) 0.6631(2) 0.0820(12) Uani 1 1 d . . . H6 H 0.6962 0.4698 0.6352 0.098 Uiso 1 1 calc R . . C8 C 0.7939(4) 0.0406(4) 0.7975(2) 0.0993(16) Uani 1 1 d . . . H8A H 0.7753 0.1280 0.8021 0.149 Uiso 1 1 calc R . . H8B H 0.8533 0.0400 0.7968 0.149 Uiso 1 1 calc R . . H8C H 0.7806 -0.0103 0.8336 0.149 Uiso 1 1 calc R . . C20 C 1.3366(3) -0.2099(5) 0.5598(2) 0.0832(13) Uani 1 1 d . . . C9 C 0.7586(3) -0.1366(4) 0.70870(18) 0.0656(10) Uani 1 1 d . . . C34 C 0.6813(3) -0.3407(5) 0.4950(2) 0.0869(13) Uani 1 1 d . . . H34 H 0.7152 -0.3513 0.5346 0.104 Uiso 1 1 calc R . . C2 C 0.6034(3) 0.3512(5) 0.7504(2) 0.0858(13) Uani 1 1 d . . . H2 H 0.5710 0.3753 0.7825 0.103 Uiso 1 1 calc R . . C15 C 0.8569(3) -0.5175(4) 0.77733(19) 0.0771(12) Uani 1 1 d . . . H15 H 0.8224 -0.4806 0.8050 0.093 Uiso 1 1 calc R . . C16 C 0.8965(4) -0.6306(5) 0.7940(3) 0.1066(17) Uani 1 1 d . . . H16 H 0.8898 -0.6704 0.8333 0.128 Uiso 1 1 calc R . . C21 C 1.2912(3) -0.0999(5) 0.5642(2) 0.0942(14) Uani 1 1 d . . . H21 H 1.3166 -0.0263 0.5836 0.113 Uiso 1 1 calc R . . C29 C 1.0954(3) -0.0393(5) 0.3963(3) 0.1011(16) Uani 1 1 d . . . H29A H 1.1534 -0.0428 0.4141 0.152 Uiso 1 1 calc R . . H29B H 1.0756 0.0481 0.3983 0.152 Uiso 1 1 calc R . . H29C H 1.0891 -0.0677 0.3517 0.152 Uiso 1 1 calc R . . C19 C 0.9138(3) -0.5158(4) 0.6769(2) 0.0871(13) Uani 1 1 d . . . H19 H 0.9177 -0.4785 0.6364 0.105 Uiso 1 1 calc R . . C12 C 0.6103(3) 0.0313(5) 0.5831(2) 0.0969(15) Uani 1 1 d . . . H12A H 0.5976 0.1201 0.5911 0.145 Uiso 1 1 calc R . . H12B H 0.5602 -0.0195 0.5807 0.145 Uiso 1 1 calc R . . H12C H 0.6332 0.0247 0.5426 0.145 Uiso 1 1 calc R . . C18 C 0.9551(4) -0.6313(5) 0.6939(4) 0.1139(18) Uani 1 1 d . . . H18 H 0.9878 -0.6701 0.6655 0.137 Uiso 1 1 calc R . . C35 C 0.5966(3) -0.3584(5) 0.4919(3) 0.1001(15) Uani 1 1 d . . . H35 H 0.5737 -0.3812 0.5293 0.120 Uiso 1 1 calc R . . C17 C 0.9473(4) -0.6872(5) 0.7524(4) 0.118(2) Uani 1 1 d . . . H17 H 0.9759 -0.7634 0.7645 0.142 Uiso 1 1 calc R . . C38 C 0.6648(3) -0.2959(7) 0.3832(3) 0.121(2) Uani 1 1 d . . . H38 H 0.6868 -0.2745 0.3452 0.145 Uiso 1 1 calc R . . C36 C 0.5464(4) -0.3431(6) 0.4353(4) 0.1204(19) Uani 1 1 d . . . H36 H 0.4889 -0.3517 0.4338 0.145 Uiso 1 1 calc R . . C37 C 0.5802(4) -0.3153(9) 0.3807(3) 0.161(3) Uani 1 1 d . . . H37 H 0.5461 -0.3092 0.3410 0.193 Uiso 1 1 calc R . . H4A H 0.812(3) -0.256(4) 0.399(2) 0.083(14) Uiso 1 1 d . . . H2A H 0.825(3) -0.314(4) 0.662(2) 0.072(13) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl2 0.0608(8) 0.2014(16) 0.1103(10) -0.0246(10) 0.0085(6) 0.0060(8) Cl1 0.1218(12) 0.0729(8) 0.1777(15) -0.0084(8) 0.0076(10) 0.0200(7) O1 0.115(2) 0.0740(18) 0.0557(17) -0.0044(13) -0.0062(14) 0.0214(16) O2 0.0686(19) 0.123(2) 0.0710(18) 0.0179(17) 0.0064(14) -0.0075(16) N1 0.075(2) 0.0553(18) 0.0618(18) 0.0004(15) 0.0027(15) -0.0004(16) N2 0.092(3) 0.059(2) 0.0518(19) 0.0008(17) 0.0088(16) 0.0035(17) N4 0.063(2) 0.080(2) 0.060(2) -0.0019(17) 0.0030(16) -0.0017(17) N3 0.061(2) 0.069(2) 0.0683(19) 0.0003(16) 0.0079(16) -0.0005(16) C26 0.061(2) 0.066(2) 0.060(2) -0.0045(18) 0.0066(18) -0.0053(19) C13 0.079(3) 0.059(2) 0.061(2) -0.003(2) 0.005(2) -0.002(2) C10 0.084(3) 0.068(3) 0.060(2) -0.0059(19) -0.003(2) -0.005(2) C30 0.063(3) 0.070(3) 0.076(3) 0.009(2) 0.0101(19) 0.009(2) C33 0.055(3) 0.068(2) 0.081(3) -0.004(2) 0.007(2) 0.0031(18) C31 0.063(2) 0.060(2) 0.059(2) -0.0027(18) 0.0060(18) 0.0013(18) C23 0.053(2) 0.076(3) 0.071(2) -0.008(2) 0.0109(18) 0.001(2) C25 0.071(3) 0.093(3) 0.084(3) 0.000(3) 0.013(2) 0.016(3) C28 0.074(3) 0.068(3) 0.076(3) 0.007(2) 0.018(2) 0.009(2) C5 0.072(3) 0.069(3) 0.084(3) 0.006(2) 0.017(2) 0.001(2) C11 0.080(3) 0.065(3) 0.065(2) -0.002(2) 0.000(2) -0.003(2) C24 0.073(3) 0.072(3) 0.078(3) -0.008(2) 0.008(2) 0.002(2) C22 0.068(3) 0.076(3) 0.113(3) -0.027(3) 0.013(2) 0.004(2) C32 0.059(2) 0.072(2) 0.057(2) 0.0006(19) 0.0044(18) 0.0025(19) C14 0.070(2) 0.049(2) 0.064(2) 0.0023(18) 0.0035(18) -0.0004(18) C3 0.093(3) 0.066(3) 0.079(3) 0.013(2) 0.022(2) 0.004(2) C27 0.074(3) 0.107(3) 0.078(3) 0.023(3) 0.000(2) -0.007(3) C7 0.080(3) 0.054(2) 0.062(2) 0.0012(19) 0.001(2) -0.0022(19) C4 0.067(2) 0.055(2) 0.066(2) 0.0037(19) 0.0026(19) -0.0007(18) C1 0.071(3) 0.066(3) 0.097(3) -0.004(2) -0.006(2) -0.002(2) C6 0.074(3) 0.064(3) 0.108(3) 0.017(2) 0.013(3) -0.004(2) C8 0.132(4) 0.069(3) 0.085(3) -0.016(2) -0.031(3) 0.011(3) C20 0.066(3) 0.110(4) 0.076(3) -0.008(3) 0.018(2) 0.002(3) C9 0.079(3) 0.057(2) 0.060(2) -0.0046(18) 0.0066(19) -0.005(2) C34 0.066(3) 0.113(4) 0.083(3) -0.016(3) 0.017(2) 0.005(2) C2 0.092(3) 0.085(3) 0.082(3) -0.006(3) 0.019(2) 0.013(3) C15 0.107(4) 0.054(2) 0.070(3) 0.003(2) 0.011(2) 0.005(2) C16 0.152(5) 0.069(3) 0.094(3) 0.007(3) -0.005(3) 0.005(3) C21 0.069(3) 0.104(4) 0.110(4) -0.033(3) 0.012(3) -0.008(3) C29 0.086(3) 0.099(4) 0.122(4) 0.035(3) 0.025(3) 0.002(3) C19 0.092(3) 0.072(3) 0.103(3) -0.002(2) 0.035(3) 0.004(3) C12 0.117(4) 0.087(3) 0.077(3) 0.004(2) -0.023(3) -0.005(3) C18 0.104(4) 0.085(4) 0.158(6) -0.009(4) 0.039(4) 0.017(3) C35 0.071(4) 0.122(4) 0.112(4) -0.018(3) 0.030(3) -0.002(3) C17 0.127(5) 0.070(3) 0.152(6) 0.010(4) -0.005(4) 0.021(3) C38 0.064(3) 0.197(6) 0.096(4) 0.047(4) -0.011(3) -0.018(3) C36 0.060(3) 0.153(5) 0.145(5) 0.011(4) 0.003(4) -0.001(3) C37 0.071(4) 0.277(10) 0.125(5) 0.064(6) -0.025(3) -0.027(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl2 C20 1.739(5) . ? Cl1 C1 1.728(5) . ? O1 C13 1.229(5) . ? O2 C32 1.230(4) . ? N1 C7 1.375(5) . ? N1 C11 1.384(5) . ? N1 C4 1.427(5) . ? N2 C13 1.371(5) . ? N2 C14 1.405(5) . ? N2 H2A 0.82(4) . ? N4 C32 1.366(5) . ? N4 C33 1.404(5) . ? N4 H4A 0.89(5) . ? N3 C26 1.373(5) . ? N3 C28 1.391(5) . ? N3 C23 1.431(5) . ? C26 C31 1.378(5) . ? C26 C27 1.488(6) . ? C13 C9 1.460(6) . ? C10 C11 1.358(6) . ? C10 C9 1.403(6) . ? C10 H10 0.9300 . ? C30 C28 1.361(6) . ? C30 C31 1.409(5) . ? C30 H30 0.9300 . ? C33 C38 1.352(7) . ? C33 C34 1.390(6) . ? C31 C32 1.470(5) . ? C23 C22 1.376(6) . ? C23 C24 1.383(6) . ? C25 C20 1.360(7) . ? C25 C24 1.386(6) . ? C25 H25 0.9300 . ? C28 C29 1.486(6) . ? C5 C4 1.367(5) . ? C5 C6 1.370(6) . ? C5 H5 0.9300 . ? C11 C12 1.485(6) . ? C24 H24 0.9300 . ? C22 C21 1.372(7) . ? C22 H22 0.9300 . ? C14 C19 1.366(5) . ? C14 C15 1.388(5) . ? C3 C4 1.374(6) . ? C3 C2 1.381(6) . ? C3 H3 0.9300 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C7 C9 1.393(5) . ? C7 C8 1.473(6) . ? C1 C2 1.368(6) . ? C1 C6 1.372(6) . ? C6 H6 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C20 C21 1.361(7) . ? C34 C35 1.373(7) . ? C34 H34 0.9300 . ? C2 H2 0.9300 . ? C15 C16 1.355(7) . ? C15 H15 0.9300 . ? C16 C17 1.392(8) . ? C16 H16 0.9300 . ? C21 H21 0.9300 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C19 C18 1.389(7) . ? C19 H19 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C18 C17 1.361(8) . ? C18 H18 0.9300 . ? C35 C36 1.343(8) . ? C35 H35 0.9300 . ? C17 H17 0.9300 . ? C38 C37 1.373(8) . ? C38 H38 0.9300 . ? C36 C37 1.347(9) . ? C36 H36 0.9300 . ? C37 H37 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 C11 111.0(3) . . ? C7 N1 C4 125.4(3) . . ? C11 N1 C4 123.6(3) . . ? C13 N2 C14 126.0(4) . . ? C13 N2 H2A 111(3) . . ? C14 N2 H2A 121(3) . . ? C32 N4 C33 128.2(4) . . ? C32 N4 H4A 121(3) . . ? C33 N4 H4A 111(3) . . ? C26 N3 C28 109.9(3) . . ? C26 N3 C23 124.5(3) . . ? C28 N3 C23 125.5(3) . . ? N3 C26 C31 107.2(3) . . ? N3 C26 C27 122.5(4) . . ? C31 C26 C27 130.3(4) . . ? O1 C13 N2 121.7(4) . . ? O1 C13 C9 123.2(3) . . ? N2 C13 C9 115.1(4) . . ? C11 C10 C9 110.0(3) . . ? C11 C10 H10 125.0 . . ? C9 C10 H10 125.0 . . ? C28 C30 C31 108.9(4) . . ? C28 C30 H30 125.6 . . ? C31 C30 H30 125.6 . . ? C38 C33 C34 117.0(4) . . ? C38 C33 N4 118.4(4) . . ? C34 C33 N4 124.6(4) . . ? C26 C31 C30 107.4(3) . . ? C26 C31 C32 124.4(3) . . ? C30 C31 C32 128.1(4) . . ? C22 C23 C24 119.1(4) . . ? C22 C23 N3 120.7(4) . . ? C24 C23 N3 120.2(4) . . ? C20 C25 C24 119.5(4) . . ? C20 C25 H25 120.2 . . ? C24 C25 H25 120.2 . . ? C30 C28 N3 106.6(3) . . ? C30 C28 C29 130.4(4) . . ? N3 C28 C29 122.9(4) . . ? C4 C5 C6 121.6(4) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C10 C11 N1 105.8(3) . . ? C10 C11 C12 131.6(4) . . ? N1 C11 C12 122.6(4) . . ? C23 C24 C25 120.0(4) . . ? C23 C24 H24 120.0 . . ? C25 C24 H24 120.0 . . ? C21 C22 C23 120.5(4) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? O2 C32 N4 122.0(4) . . ? O2 C32 C31 122.8(3) . . ? N4 C32 C31 115.2(3) . . ? C19 C14 C15 119.4(4) . . ? C19 C14 N2 118.5(4) . . ? C15 C14 N2 122.0(4) . . ? C4 C3 C2 120.1(4) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? N1 C7 C9 106.2(3) . . ? N1 C7 C8 123.1(3) . . ? C9 C7 C8 130.5(4) . . ? C5 C4 C3 118.9(4) . . ? C5 C4 N1 120.3(4) . . ? C3 C4 N1 120.7(3) . . ? C2 C1 C6 120.2(4) . . ? C2 C1 Cl1 119.8(4) . . ? C6 C1 Cl1 119.9(4) . . ? C5 C6 C1 119.2(4) . . ? C5 C6 H6 120.4 . . ? C1 C6 H6 120.4 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C25 C20 C21 121.0(4) . . ? C25 C20 Cl2 118.6(4) . . ? C21 C20 Cl2 120.5(4) . . ? C7 C9 C10 107.0(4) . . ? C7 C9 C13 124.4(4) . . ? C10 C9 C13 128.6(4) . . ? C35 C34 C33 120.8(5) . . ? C35 C34 H34 119.6 . . ? C33 C34 H34 119.6 . . ? C1 C2 C3 120.0(4) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C16 C15 C14 120.3(4) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C17 120.1(5) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C20 C21 C22 119.9(4) . . ? C20 C21 H21 120.1 . . ? C22 C21 H21 120.1 . . ? 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 . . ? C14 C19 C18 120.5(5) . . ? C14 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C17 C18 C19 119.6(5) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? C36 C35 C34 120.6(5) . . ? C36 C35 H35 119.7 . . ? C34 C35 H35 119.7 . . ? C18 C17 C16 120.0(5) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C33 C38 C37 121.7(5) . . ? C33 C38 H38 119.2 . . ? C37 C38 H38 119.2 . . ? C35 C36 C37 119.5(5) . . ? C35 C36 H36 120.3 . . ? C37 C36 H36 120.3 . . ? C36 C37 C38 120.4(6) . . ? C36 C37 H37 119.8 . . ? C38 C37 H37 119.8 . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 67.84 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.457 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.067