data_ww230 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H48 Cl4 F2 N2 O2' _chemical_formula_weight 720.56 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' 'F' 'F' 0.0171 0.0103 '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 12.3348(9) _cell_length_b 13.9342(11) _cell_length_c 22.0311(17) _cell_angle_alpha 90.00 _cell_angle_beta 101.4030(10) _cell_angle_gamma 90.00 _cell_volume 3711.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9767 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 27.1 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 0.362 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9053 _exptl_absorpt_correction_T_max 0.9647 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 62600 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0257 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 27.14 _reflns_number_total 8209 _reflns_number_gt 6615 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 v2009.3.0 (Bruker-AXS, 2009)' _computing_cell_refinement 'SAINT 7.46A (Bruker-AXS, 2009)' _computing_data_reduction 'SAINT 7.46A (Bruker-AXS, 2009)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0608P)^2^+7.0524P] 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 8209 _refine_ls_number_parameters 447 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0718 _refine_ls_R_factor_gt 0.0579 _refine_ls_wR_factor_ref 0.1547 _refine_ls_wR_factor_gt 0.1442 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.028 _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 0.31357(12) 0.82029(11) 0.69147(7) 0.0147(3) Uani 1 1 d . . . O2 O 0.39616(14) 0.80585(13) 0.94758(7) 0.0244(4) Uani 1 1 d . . . N1 N 0.40950(14) 0.78173(12) 0.61380(8) 0.0118(3) Uani 1 1 d . . . N2 N 0.35572(14) 0.66088(12) 0.66359(8) 0.0123(3) Uani 1 1 d . . . C1 C 0.35968(16) 0.75672(15) 0.65990(9) 0.0118(4) Uani 1 1 d . . . C2 C 0.43849(17) 0.69783(16) 0.58632(10) 0.0154(4) Uani 1 1 d . . . H2 H 0.4750 0.6941 0.5523 0.019 Uiso 1 1 calc R . . C3 C 0.40525(17) 0.62309(16) 0.61684(10) 0.0153(4) Uani 1 1 d . . . H3 H 0.4138 0.5570 0.6082 0.018 Uiso 1 1 calc R . . C4 C 0.33512(18) 0.81226(15) 0.75733(9) 0.0133(4) Uani 1 1 d . . . C5 C 0.44269(18) 0.81484(16) 0.79043(10) 0.0173(4) Uani 1 1 d . . . H5 H 0.5033 0.8181 0.7697 0.021 Uiso 1 1 calc R . . C6 C 0.46004(18) 0.81263(17) 0.85446(10) 0.0188(5) Uani 1 1 d . . . H6 H 0.5333 0.8136 0.8782 0.023 Uiso 1 1 calc R . . C7 C 0.37032(19) 0.80905(16) 0.88421(10) 0.0176(4) Uani 1 1 d . . . C8 C 0.26295(18) 0.80876(17) 0.85004(10) 0.0185(4) Uani 1 1 d . . . H8 H 0.2018 0.8076 0.8704 0.022 Uiso 1 1 calc R . . C9 C 0.24577(18) 0.81017(16) 0.78574(10) 0.0168(4) Uani 1 1 d . . . H9 H 0.1728 0.8097 0.7617 0.020 Uiso 1 1 calc R . . C10 C 0.3044(2) 0.8060(2) 0.97855(11) 0.0303(6) Uani 1 1 d . . . H10A H 0.2601 0.7479 0.9674 0.045 Uiso 1 1 calc R . . H10B H 0.2585 0.8627 0.9660 0.045 Uiso 1 1 calc R . . H10C H 0.3318 0.8074 1.0234 0.045 Uiso 1 1 calc R . . C11 C 0.42552(18) 0.87999(15) 0.59521(9) 0.0136(4) Uani 1 1 d . . . C12 C 0.33543(18) 0.92740(16) 0.55854(10) 0.0162(4) Uani 1 1 d . . . C13 C 0.3529(2) 1.02190(17) 0.54241(10) 0.0210(5) Uani 1 1 d . . . H13 H 0.2937 1.0568 0.5181 0.025 Uiso 1 1 calc R . . C14 C 0.4543(2) 1.06625(17) 0.56089(11) 0.0225(5) Uani 1 1 d . . . H14 H 0.4642 1.1307 0.5490 0.027 Uiso 1 1 calc R . . C15 C 0.5409(2) 1.01696(17) 0.59652(11) 0.0204(5) Uani 1 1 d . . . H15 H 0.6104 1.0480 0.6088 0.024 Uiso 1 1 calc R . . C16 C 0.52871(18) 0.92210(16) 0.61507(10) 0.0160(4) Uani 1 1 d . . . C17 C 0.22584(19) 0.87718(18) 0.53605(11) 0.0231(5) Uani 1 1 d . . . H17 H 0.2119 0.8344 0.5701 0.028 Uiso 1 1 calc R . . C18 C 0.2314(2) 0.8141(2) 0.48019(14) 0.0387(7) Uani 1 1 d . . . H18A H 0.2443 0.8543 0.4458 0.058 Uiso 1 1 calc R . . H18B H 0.1614 0.7795 0.4677 0.058 Uiso 1 1 calc R . . H18C H 0.2920 0.7679 0.4912 0.058 Uiso 1 1 calc R . . C19 C 0.1279(2) 0.9457(2) 0.51969(12) 0.0292(6) Uani 1 1 d . . . H19A H 0.1270 0.9892 0.5545 0.044 Uiso 1 1 calc R . . H19B H 0.0590 0.9088 0.5110 0.044 Uiso 1 1 calc R . . H19C H 0.1350 0.9832 0.4830 0.044 Uiso 1 1 calc R . . C20 C 0.62508(18) 0.87087(17) 0.65552(11) 0.0212(5) Uani 1 1 d . . . H20 H 0.5974 0.8087 0.6693 0.025 Uiso 1 1 calc R . . C21 C 0.7153(2) 0.8485(2) 0.61856(15) 0.0362(7) Uani 1 1 d . . . H21A H 0.6841 0.8090 0.5826 0.054 Uiso 1 1 calc R . . H21B H 0.7759 0.8138 0.6450 0.054 Uiso 1 1 calc R . . H21C H 0.7435 0.9087 0.6045 0.054 Uiso 1 1 calc R . . C22 C 0.6713(2) 0.9305(2) 0.71323(13) 0.0322(6) Uani 1 1 d . . . H22A H 0.7034 0.9900 0.7009 0.048 Uiso 1 1 calc R . . H22B H 0.7286 0.8937 0.7407 0.048 Uiso 1 1 calc R . . H22C H 0.6115 0.9460 0.7350 0.048 Uiso 1 1 calc R . . C23 C 0.28947(17) 0.61161(15) 0.70150(10) 0.0136(4) Uani 1 1 d . . . C24 C 0.34177(17) 0.57186(15) 0.75806(10) 0.0139(4) Uani 1 1 d . . . C25 C 0.27307(19) 0.53682(16) 0.79606(10) 0.0173(4) Uani 1 1 d . . . H25 H 0.3049 0.5102 0.8352 0.021 Uiso 1 1 calc R . . C26 C 0.15896(19) 0.54015(16) 0.77775(11) 0.0186(4) Uani 1 1 d . . . H26 H 0.1137 0.5182 0.8051 0.022 Uiso 1 1 calc R . . C27 C 0.11056(18) 0.57499(16) 0.72009(11) 0.0191(5) Uani 1 1 d . . . H27 H 0.0323 0.5738 0.7074 0.023 Uiso 1 1 calc R . . C28 C 0.17508(17) 0.61206(15) 0.68009(10) 0.0150(4) Uani 1 1 d . . . C29 C 0.46704(18) 0.56412(16) 0.77561(10) 0.0167(4) Uani 1 1 d . . . H29 H 0.4994 0.6215 0.7586 0.020 Uiso 1 1 calc R . . C30 C 0.50721(19) 0.47421(18) 0.74629(12) 0.0237(5) Uani 1 1 d . . . H30A H 0.4835 0.4168 0.7658 0.036 Uiso 1 1 calc R . . H30B H 0.5881 0.4752 0.7525 0.036 Uiso 1 1 calc R . . H30C H 0.4756 0.4733 0.7018 0.036 Uiso 1 1 calc R . . C31 C 0.5111(2) 0.56151(18) 0.84553(11) 0.0236(5) Uani 1 1 d . . . H31A H 0.4799 0.6152 0.8651 0.035 Uiso 1 1 calc R . . H31B H 0.5919 0.5667 0.8539 0.035 Uiso 1 1 calc R . . H31C H 0.4896 0.5009 0.8624 0.035 Uiso 1 1 calc R . . C32 C 0.12028(18) 0.64944(17) 0.61665(10) 0.0188(5) Uani 1 1 d . . . H32 H 0.1799 0.6741 0.5959 0.023 Uiso 1 1 calc R . . C33 C 0.0413(2) 0.73255(19) 0.62113(12) 0.0263(5) Uani 1 1 d . . . H33A H -0.0196 0.7098 0.6400 0.039 Uiso 1 1 calc R . . H33B H 0.0115 0.7574 0.5796 0.039 Uiso 1 1 calc R . . H33C H 0.0813 0.7837 0.6467 0.039 Uiso 1 1 calc R . . C34 C 0.0609(2) 0.56791(19) 0.57669(12) 0.0300(6) Uani 1 1 d . . . H34A H 0.1135 0.5161 0.5740 0.045 Uiso 1 1 calc R . . H34B H 0.0305 0.5922 0.5350 0.045 Uiso 1 1 calc R . . H34C H 0.0007 0.5433 0.5954 0.045 Uiso 1 1 calc R . . C35 C 0.6656(3) 0.5305(2) 0.57735(16) 0.0327(7) Uani 0.8850(18) 1 d PD A 1 H35C H 0.5962 0.4978 0.5816 0.039 Uiso 0.8850(18) 1 calc PR A 1 H35D H 0.6468 0.5818 0.5460 0.039 Uiso 0.8850(18) 1 calc PR A 1 Cl1 Cl 0.75485(9) 0.44730(8) 0.55240(7) 0.0561(3) Uani 0.8850(18) 1 d PD A 1 Cl2 Cl 0.72818(9) 0.58221(8) 0.64958(5) 0.0512(3) Uani 0.8850(18) 1 d PD A 1 C35D C 0.6618(15) 0.4809(18) 0.5493(9) 0.0327(7) Uani 0.1150(18) 1 d PD A 2 H35A H 0.6252 0.5298 0.5196 0.039 Uiso 0.1150(18) 1 calc PR A 2 H35B H 0.6105 0.4261 0.5484 0.039 Uiso 0.1150(18) 1 calc PR A 2 Cl1D Cl 0.6925(7) 0.5300(6) 0.6239(5) 0.0561(3) Uani 0.1150(18) 1 d PD A 2 Cl2D Cl 0.7857(8) 0.4416(6) 0.5275(4) 0.0512(3) Uani 0.1150(18) 1 d PD A 2 C36 C 0.3675(3) 0.7297(2) 0.33931(16) 0.0351(7) Uani 0.9175(14) 1 d PD B 1 H36C H 0.3634 0.6592 0.3339 0.042 Uiso 0.9175(14) 1 calc PR B 1 H36D H 0.3960 0.7436 0.3837 0.042 Uiso 0.9175(14) 1 calc PR B 1 Cl3 Cl 0.45891(8) 0.77919(6) 0.29388(5) 0.0485(2) Uani 0.9175(14) 1 d PD B 1 Cl4 Cl 0.23469(6) 0.78027(6) 0.31588(4) 0.0414(2) Uani 0.9175(14) 1 d PD B 1 C36D C 0.3700(17) 0.808(2) 0.2580(12) 0.0351(7) Uani 0.0825(14) 1 d PDU B 2 H36A H 0.4107 0.8698 0.2596 0.042 Uiso 0.0825(14) 1 calc PR B 2 H36B H 0.3783 0.7721 0.2206 0.042 Uiso 0.0825(14) 1 calc PR B 2 Cl3D Cl 0.2309(8) 0.8262(7) 0.2613(5) 0.0485(2) Uani 0.0825(14) 1 d PD B 2 Cl4D Cl 0.4148(9) 0.7367(8) 0.3297(5) 0.0414(2) Uani 0.0825(14) 1 d PD B 2 F1 F 0.45457(15) 0.29299(11) 0.52266(7) 0.0346(4) Uani 1 1 d . . . F2 F 0.44671(14) 0.41540(12) 0.58892(8) 0.0378(4) Uani 1 1 d . . . H1 H 0.456(3) 0.357(3) 0.5562(16) 0.045 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 O1 0.0198(7) 0.0135(7) 0.0113(7) 0.0002(6) 0.0045(6) 0.0040(6) O2 0.0212(8) 0.0400(10) 0.0118(8) -0.0018(7) 0.0025(6) 0.0017(7) N1 0.0126(8) 0.0122(8) 0.0108(8) 0.0008(7) 0.0025(6) -0.0003(6) N2 0.0130(8) 0.0112(8) 0.0130(8) 0.0004(7) 0.0031(7) 0.0004(6) C1 0.0112(9) 0.0133(10) 0.0103(9) 0.0005(7) 0.0003(7) 0.0005(7) C2 0.0163(10) 0.0159(10) 0.0149(10) -0.0021(8) 0.0050(8) 0.0021(8) C3 0.0158(10) 0.0158(10) 0.0147(10) -0.0014(8) 0.0041(8) 0.0018(8) C4 0.0191(10) 0.0112(9) 0.0096(9) -0.0006(8) 0.0034(8) 0.0001(8) C5 0.0172(10) 0.0180(11) 0.0182(11) -0.0008(9) 0.0071(8) -0.0012(8) C6 0.0151(10) 0.0234(12) 0.0171(11) -0.0030(9) 0.0012(8) -0.0009(9) C7 0.0214(11) 0.0188(11) 0.0124(10) -0.0019(8) 0.0028(8) 0.0003(9) C8 0.0175(10) 0.0238(12) 0.0154(10) -0.0012(9) 0.0060(8) 0.0010(9) C9 0.0143(10) 0.0203(11) 0.0156(10) -0.0004(9) 0.0024(8) 0.0017(8) C10 0.0266(13) 0.0509(17) 0.0147(11) 0.0007(11) 0.0072(10) 0.0035(12) C11 0.0188(10) 0.0114(10) 0.0118(9) 0.0012(8) 0.0061(8) 0.0000(8) C12 0.0195(10) 0.0184(11) 0.0110(9) 0.0006(8) 0.0042(8) 0.0029(8) C13 0.0280(12) 0.0191(11) 0.0163(11) 0.0050(9) 0.0049(9) 0.0069(9) C14 0.0341(13) 0.0131(11) 0.0219(11) 0.0033(9) 0.0099(10) -0.0002(9) C15 0.0245(11) 0.0173(11) 0.0201(11) -0.0005(9) 0.0063(9) -0.0060(9) C16 0.0189(10) 0.0157(10) 0.0140(10) 0.0002(8) 0.0053(8) 0.0000(8) C17 0.0191(11) 0.0266(13) 0.0210(11) 0.0077(10) -0.0025(9) 0.0006(9) C18 0.0345(15) 0.0321(15) 0.0403(16) -0.0114(13) -0.0152(13) 0.0078(12) C19 0.0213(12) 0.0425(16) 0.0220(12) 0.0045(11) 0.0000(10) 0.0075(11) C20 0.0154(10) 0.0212(12) 0.0261(12) 0.0074(9) 0.0019(9) -0.0026(9) C21 0.0228(13) 0.0391(16) 0.0495(18) 0.0149(14) 0.0142(12) 0.0082(11) C22 0.0299(13) 0.0324(14) 0.0289(13) 0.0071(11) -0.0075(11) -0.0123(11) C23 0.0157(10) 0.0109(10) 0.0150(10) 0.0000(8) 0.0054(8) -0.0011(8) C24 0.0160(10) 0.0103(9) 0.0152(10) -0.0012(8) 0.0029(8) -0.0004(8) C25 0.0225(11) 0.0133(10) 0.0162(10) 0.0023(8) 0.0039(9) -0.0004(8) C26 0.0207(11) 0.0145(10) 0.0229(11) 0.0027(9) 0.0101(9) -0.0012(8) C27 0.0144(10) 0.0168(11) 0.0263(12) 0.0020(9) 0.0047(9) -0.0002(8) C28 0.0163(10) 0.0117(10) 0.0166(10) -0.0004(8) 0.0020(8) 0.0003(8) C29 0.0153(10) 0.0155(10) 0.0185(11) 0.0032(8) 0.0011(8) -0.0015(8) C30 0.0187(11) 0.0245(12) 0.0270(12) -0.0007(10) 0.0027(9) 0.0047(9) C31 0.0222(11) 0.0254(12) 0.0202(12) 0.0032(9) -0.0029(9) -0.0025(9) C32 0.0160(10) 0.0192(11) 0.0198(11) 0.0036(9) 0.0004(8) -0.0010(8) C33 0.0241(12) 0.0260(13) 0.0266(13) 0.0046(10) -0.0006(10) 0.0058(10) C34 0.0350(14) 0.0255(13) 0.0245(13) 0.0000(10) -0.0061(11) -0.0041(11) C35 0.0272(14) 0.0332(18) 0.0378(19) 0.0085(14) 0.0065(13) 0.0016(13) Cl1 0.0445(5) 0.0437(5) 0.0815(8) -0.0121(5) 0.0158(5) 0.0064(4) Cl2 0.0549(6) 0.0506(6) 0.0450(5) -0.0004(4) 0.0024(4) 0.0010(4) C35D 0.0272(14) 0.0332(18) 0.0378(19) 0.0085(14) 0.0065(13) 0.0016(13) Cl1D 0.0445(5) 0.0437(5) 0.0815(8) -0.0121(5) 0.0158(5) 0.0064(4) Cl2D 0.0549(6) 0.0506(6) 0.0450(5) -0.0004(4) 0.0024(4) 0.0010(4) C36 0.0296(16) 0.0371(18) 0.0398(18) 0.0024(14) 0.0100(14) -0.0023(14) Cl3 0.0483(5) 0.0389(5) 0.0666(6) -0.0021(4) 0.0317(4) 0.0004(4) Cl4 0.0308(4) 0.0424(5) 0.0510(5) -0.0096(4) 0.0082(3) 0.0024(3) C36D 0.0296(16) 0.0371(18) 0.0398(18) 0.0024(14) 0.0100(14) -0.0023(14) Cl3D 0.0483(5) 0.0389(5) 0.0666(6) -0.0021(4) 0.0317(4) 0.0004(4) Cl4D 0.0308(4) 0.0424(5) 0.0510(5) -0.0096(4) 0.0082(3) 0.0024(3) F1 0.0549(10) 0.0230(8) 0.0336(8) -0.0042(6) 0.0271(8) -0.0031(7) F2 0.0439(10) 0.0241(8) 0.0494(10) -0.0145(7) 0.0191(8) -0.0023(7) _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 C1 1.322(2) . ? O1 C4 1.427(2) . ? O2 C7 1.370(3) . ? O2 C10 1.432(3) . ? N1 C1 1.333(3) . ? N1 C2 1.395(3) . ? N1 C11 1.454(3) . ? N2 C1 1.339(3) . ? N2 C3 1.400(3) . ? N2 C23 1.451(3) . ? C2 C3 1.347(3) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C4 C9 1.371(3) . ? C4 C5 1.382(3) . ? C5 C6 1.385(3) . ? C5 H5 0.9500 . ? C6 C7 1.394(3) . ? C6 H6 0.9500 . ? C7 C8 1.388(3) . ? C8 C9 1.390(3) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C16 1.391(3) . ? C11 C12 1.403(3) . ? C12 C13 1.392(3) . ? C12 C17 1.516(3) . ? C13 C14 1.381(4) . ? C13 H13 0.9500 . ? C14 C15 1.377(3) . ? C14 H14 0.9500 . ? C15 C16 1.400(3) . ? C15 H15 0.9500 . ? C16 C20 1.516(3) . ? C17 C18 1.525(4) . ? C17 C19 1.526(3) . ? C17 H17 1.0000 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C22 1.532(4) . ? C20 C21 1.535(4) . ? C20 H20 1.0000 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 C28 1.396(3) . ? C23 C24 1.399(3) . ? C24 C25 1.392(3) . ? C24 C29 1.521(3) . ? C25 C26 1.386(3) . ? C25 H25 0.9500 . ? C26 C27 1.380(3) . ? C26 H26 0.9500 . ? C27 C28 1.398(3) . ? C27 H27 0.9500 . ? C28 C32 1.519(3) . ? C29 C31 1.529(3) . ? C29 C30 1.536(3) . ? C29 H29 1.0000 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 C33 1.529(3) . ? C32 C34 1.532(3) . ? C32 H32 1.0000 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 Cl1 1.759(3) . ? C35 Cl2 1.778(4) . ? C35 H35C 0.9900 . ? C35 H35D 0.9900 . ? C35D Cl1D 1.751(17) . ? C35D Cl2D 1.777(16) . ? C35D H35A 0.9900 . ? C35D H35B 0.9900 . ? C36 Cl4 1.764(4) . ? C36 Cl3 1.787(4) . ? C36 H36C 0.9900 . ? C36 H36D 0.9900 . ? C36D Cl3D 1.749(18) . ? C36D Cl4D 1.857(18) . ? C36D H36A 0.9900 . ? C36D H36B 0.9900 . ? F1 H1 1.16(4) . ? F2 H1 1.11(4) . ? 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 117.99(16) . . ? C7 O2 C10 116.03(18) . . ? C1 N1 C2 107.92(17) . . ? C1 N1 C11 124.72(17) . . ? C2 N1 C11 127.31(17) . . ? C1 N2 C3 107.69(17) . . ? C1 N2 C23 122.55(17) . . ? C3 N2 C23 128.51(18) . . ? O1 C1 N1 122.45(19) . . ? O1 C1 N2 127.68(19) . . ? N1 C1 N2 109.56(18) . . ? C3 C2 N1 107.58(18) . . ? C3 C2 H2 126.2 . . ? N1 C2 H2 126.2 . . ? C2 C3 N2 107.25(19) . . ? C2 C3 H3 126.4 . . ? N2 C3 H3 126.4 . . ? C9 C4 C5 122.3(2) . . ? C9 C4 O1 117.44(19) . . ? C5 C4 O1 120.05(18) . . ? C4 C5 C6 118.4(2) . . ? C4 C5 H5 120.8 . . ? C6 C5 H5 120.8 . . ? C5 C6 C7 120.2(2) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? O2 C7 C8 123.9(2) . . ? O2 C7 C6 115.7(2) . . ? C8 C7 C6 120.4(2) . . ? C7 C8 C9 119.3(2) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C4 C9 C8 119.4(2) . . ? C4 C9 H9 120.3 . . ? C8 C9 H9 120.3 . . ? O2 C10 H10A 109.5 . . ? O2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 123.6(2) . . ? C16 C11 N1 118.40(19) . . ? C12 C11 N1 117.98(19) . . ? C13 C12 C11 116.6(2) . . ? C13 C12 C17 121.8(2) . . ? C11 C12 C17 121.6(2) . . ? C14 C13 C12 121.7(2) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C15 C14 C13 120.0(2) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 121.4(2) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? C11 C16 C15 116.8(2) . . ? C11 C16 C20 123.3(2) . . ? C15 C16 C20 119.9(2) . . ? C12 C17 C18 110.5(2) . . ? C12 C17 C19 113.7(2) . . ? C18 C17 C19 109.3(2) . . ? C12 C17 H17 107.7 . . ? C18 C17 H17 107.7 . . ? C19 C17 H17 107.7 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C16 C20 C22 110.6(2) . . ? C16 C20 C21 110.5(2) . . ? C22 C20 C21 111.1(2) . . ? C16 C20 H20 108.2 . . ? C22 C20 H20 108.2 . . ? C21 C20 H20 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 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 . . ? C28 C23 C24 124.03(19) . . ? C28 C23 N2 116.74(18) . . ? C24 C23 N2 119.12(18) . . ? C25 C24 C23 116.49(19) . . ? C25 C24 C29 122.07(19) . . ? C23 C24 C29 121.40(19) . . ? C26 C25 C24 121.1(2) . . ? C26 C25 H25 119.4 . . ? C24 C25 H25 119.4 . . ? C27 C26 C25 120.6(2) . . ? C27 C26 H26 119.7 . . ? C25 C26 H26 119.7 . . ? C26 C27 C28 120.9(2) . . ? C26 C27 H27 119.6 . . ? C28 C27 H27 119.6 . . ? C23 C28 C27 116.7(2) . . ? C23 C28 C32 123.24(19) . . ? C27 C28 C32 120.10(19) . . ? C24 C29 C31 113.49(19) . . ? C24 C29 C30 110.30(18) . . ? C31 C29 C30 108.93(19) . . ? C24 C29 H29 108.0 . . ? C31 C29 H29 108.0 . . ? C30 C29 H29 108.0 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C28 C32 C33 111.94(19) . . ? C28 C32 C34 110.46(19) . . ? C33 C32 C34 111.1(2) . . ? C28 C32 H32 107.7 . . ? C33 C32 H32 107.7 . . ? C34 C32 H32 107.7 . . ? C32 C33 H33A 109.5 . . ? C32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C32 C34 H34A 109.5 . . ? C32 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C32 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? Cl1 C35 Cl2 111.05(17) . . ? Cl1 C35 H35C 109.4 . . ? Cl2 C35 H35C 109.4 . . ? Cl1 C35 H35D 109.4 . . ? Cl2 C35 H35D 109.4 . . ? H35C C35 H35D 108.0 . . ? Cl1D C35D Cl2D 109.6(10) . . ? Cl1D C35D H35A 109.7 . . ? Cl2D C35D H35A 109.7 . . ? Cl1D C35D H35B 109.7 . . ? Cl2D C35D H35B 109.7 . . ? H35A C35D H35B 108.2 . . ? Cl4 C36 Cl3 109.53(18) . . ? Cl4 C36 H36C 109.8 . . ? Cl3 C36 H36C 109.8 . . ? Cl4 C36 H36D 109.8 . . ? Cl3 C36 H36D 109.8 . . ? H36C C36 H36D 108.2 . . ? Cl3D C36D Cl4D 99.9(11) . . ? Cl3D C36D H36A 111.8 . . ? Cl4D C36D H36A 111.8 . . ? Cl3D C36D H36B 111.8 . . ? Cl4D C36D H36B 111.8 . . ? H36A C36D H36B 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 C4 O1 C1 N1 -134.5(2) . . . . ? C4 O1 C1 N2 52.5(3) . . . . ? C2 N1 C1 O1 -173.83(18) . . . . ? C11 N1 C1 O1 4.0(3) . . . . ? C2 N1 C1 N2 0.3(2) . . . . ? C11 N1 C1 N2 178.16(18) . . . . ? C3 N2 C1 O1 173.32(19) . . . . ? C23 N2 C1 O1 5.1(3) . . . . ? C3 N2 C1 N1 -0.4(2) . . . . ? C23 N2 C1 N1 -168.62(18) . . . . ? C1 N1 C2 C3 -0.1(2) . . . . ? C11 N1 C2 C3 -177.8(2) . . . . ? N1 C2 C3 N2 -0.2(2) . . . . ? C1 N2 C3 C2 0.4(2) . . . . ? C23 N2 C3 C2 167.6(2) . . . . ? C1 O1 C4 C9 -127.6(2) . . . . ? C1 O1 C4 C5 57.7(3) . . . . ? C9 C4 C5 C6 1.8(3) . . . . ? O1 C4 C5 C6 176.19(19) . . . . ? C4 C5 C6 C7 -0.8(3) . . . . ? C10 O2 C7 C8 -2.4(3) . . . . ? C10 O2 C7 C6 177.6(2) . . . . ? C5 C6 C7 O2 179.2(2) . . . . ? C5 C6 C7 C8 -0.7(4) . . . . ? O2 C7 C8 C9 -178.7(2) . . . . ? C6 C7 C8 C9 1.3(4) . . . . ? C5 C4 C9 C8 -1.2(3) . . . . ? O1 C4 C9 C8 -175.81(19) . . . . ? C7 C8 C9 C4 -0.3(3) . . . . ? C1 N1 C11 C16 100.4(2) . . . . ? C2 N1 C11 C16 -82.2(3) . . . . ? C1 N1 C11 C12 -79.1(3) . . . . ? C2 N1 C11 C12 98.3(2) . . . . ? C16 C11 C12 C13 -0.5(3) . . . . ? N1 C11 C12 C13 178.95(18) . . . . ? C16 C11 C12 C17 177.7(2) . . . . ? N1 C11 C12 C17 -2.9(3) . . . . ? C11 C12 C13 C14 0.8(3) . . . . ? C17 C12 C13 C14 -177.3(2) . . . . ? C12 C13 C14 C15 -0.4(4) . . . . ? C13 C14 C15 C16 -0.4(4) . . . . ? C12 C11 C16 C15 -0.2(3) . . . . ? N1 C11 C16 C15 -179.69(18) . . . . ? C12 C11 C16 C20 179.0(2) . . . . ? N1 C11 C16 C20 -0.5(3) . . . . ? C14 C15 C16 C11 0.7(3) . . . . ? C14 C15 C16 C20 -178.6(2) . . . . ? C13 C12 C17 C18 98.7(3) . . . . ? C11 C12 C17 C18 -79.3(3) . . . . ? C13 C12 C17 C19 -24.5(3) . . . . ? C11 C12 C17 C19 157.4(2) . . . . ? C11 C16 C20 C22 -126.3(2) . . . . ? C15 C16 C20 C22 52.8(3) . . . . ? C11 C16 C20 C21 110.2(3) . . . . ? C15 C16 C20 C21 -70.7(3) . . . . ? C1 N2 C23 C28 73.0(3) . . . . ? C3 N2 C23 C28 -92.6(3) . . . . ? C1 N2 C23 C24 -103.4(2) . . . . ? C3 N2 C23 C24 91.0(3) . . . . ? C28 C23 C24 C25 -4.3(3) . . . . ? N2 C23 C24 C25 171.78(19) . . . . ? C28 C23 C24 C29 173.4(2) . . . . ? N2 C23 C24 C29 -10.5(3) . . . . ? C23 C24 C25 C26 1.1(3) . . . . ? C29 C24 C25 C26 -176.6(2) . . . . ? C24 C25 C26 C27 2.6(3) . . . . ? C25 C26 C27 C28 -3.2(3) . . . . ? C24 C23 C28 C27 3.8(3) . . . . ? N2 C23 C28 C27 -172.43(19) . . . . ? C24 C23 C28 C32 -175.7(2) . . . . ? N2 C23 C28 C32 8.1(3) . . . . ? C26 C27 C28 C23 0.1(3) . . . . ? C26 C27 C28 C32 179.6(2) . . . . ? C25 C24 C29 C31 -27.6(3) . . . . ? C23 C24 C29 C31 154.8(2) . . . . ? C25 C24 C29 C30 94.9(2) . . . . ? C23 C24 C29 C30 -82.7(2) . . . . ? C23 C28 C32 C33 -120.3(2) . . . . ? C27 C28 C32 C33 60.3(3) . . . . ? C23 C28 C32 C34 115.3(2) . . . . ? C27 C28 C32 C34 -64.1(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A F2 H1 F1 1.11(4) 1.16(4) 2.260(2) 172(3) . _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.14 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.062 _refine_diff_density_min -1.045 _refine_diff_density_rms 0.075