data_'CLTCFA' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Clotrimazole-Caffeic acid-anisole' ; _chemical_name_common 'Clotrimazole-Caffeic acid-anisole' _chemical_melting_point 414 _chemical_formula_moiety 'C23 H17 Cl N2, C9 H7 O4, C7 H8 O' _chemical_formula_sum 'C39 H32 Cl N2 O5' _chemical_formula_weight 644.12 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' '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' 'H' 'H' 0.0000 0.0000 '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' 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 12.4974(17) _cell_length_b 14.527(2) _cell_length_c 17.789(2) _cell_angle_alpha 90.00 _cell_angle_beta 96.028(2) _cell_angle_gamma 90.00 _cell_volume 3211.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5662 _cell_measurement_theta_min 1.64 _cell_measurement_theta_max 25.00 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1348 _exptl_absorpt_coefficient_mu 0.168 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30355 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0181 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5662 _reflns_number_gt 4791 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1432P)^2^+1.8985P] 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 5662 _refine_ls_number_parameters 425 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0840 _refine_ls_R_factor_gt 0.0754 _refine_ls_wR_factor_ref 0.2375 _refine_ls_wR_factor_gt 0.2285 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _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 0.40904(10) 0.61360(8) 0.11746(7) 0.0948(4) Uani 1 1 d . . . N1 N 0.28275(17) 0.41787(15) 0.08280(12) 0.0405(5) Uani 1 1 d . . . N2 N 0.16735(19) 0.45740(18) -0.00987(14) 0.0509(6) Uani 1 1 d . . . H2A H 0.1197 0.4885 -0.0375 0.061 Uiso 1 1 calc R . . C9 C 0.3033(2) 0.31933(18) 0.19226(15) 0.0395(6) Uani 1 1 d . . . C1 C 0.3413(2) 0.41152(18) 0.16065(14) 0.0388(6) Uani 1 1 d . . . C17 C 0.3094(2) 0.4952(2) 0.20641(16) 0.0476(7) Uani 1 1 d . . . C14 C 0.2113(2) 0.48167(19) 0.05758(16) 0.0428(6) Uani 1 1 d . . . H14 H 0.1951 0.5347 0.0835 0.051 Uiso 1 1 calc R . . C10 C 0.1947(2) 0.2953(2) 0.17977(19) 0.0512(7) Uani 1 1 d . . . H10 H 0.1469 0.3341 0.1515 0.061 Uiso 1 1 calc R . . C7 C 0.5293(3) 0.4253(2) 0.2250(2) 0.0588(8) Uani 1 1 d . . . C15 C 0.2808(2) 0.3495(2) 0.02873(17) 0.0514(7) Uani 1 1 d . . . H15 H 0.3213 0.2957 0.0316 0.062 Uiso 1 1 calc R . . C11 C 0.1574(3) 0.2149(2) 0.2087(2) 0.0601(8) Uani 1 1 d . . . H11 H 0.0848 0.2001 0.1997 0.072 Uiso 1 1 calc R . . C18 C 0.2491(3) 0.4840(3) 0.26743(19) 0.0627(9) Uani 1 1 d . . . H18 H 0.2271 0.4252 0.2796 0.075 Uiso 1 1 calc R . . C12 C 0.2259(3) 0.1564(2) 0.2505(2) 0.0649(9) Uani 1 1 d . . . H12 H 0.2002 0.1026 0.2705 0.078 Uiso 1 1 calc R . . C8 C 0.3713(3) 0.2591(2) 0.2333(2) 0.0583(8) Uani 1 1 d . . . H8 H 0.4443 0.2727 0.2417 0.070 Uiso 1 1 calc R . . C2 C 0.4641(2) 0.41228(19) 0.15747(17) 0.0448(7) Uani 1 1 d . . . C22 C 0.3408(3) 0.5854(2) 0.1909(2) 0.0659(9) Uani 1 1 d . . . C3 C 0.5120(3) 0.3990(3) 0.0920(2) 0.0699(10) Uani 1 1 d . . . H3 H 0.4699 0.3918 0.0460 0.084 Uiso 1 1 calc R . . C16 C 0.2089(3) 0.3759(2) -0.02886(18) 0.0579(8) Uani 1 1 d . . . H16 H 0.1910 0.3438 -0.0737 0.070 Uiso 1 1 calc R . . C13 C 0.3328(3) 0.1785(3) 0.2623(2) 0.0743(11) Uani 1 1 d . . . H13 H 0.3802 0.1389 0.2901 0.089 Uiso 1 1 calc R . . C5 C 0.6869(3) 0.4083(3) 0.1630(4) 0.0930(15) Uani 1 1 d . . . H5 H 0.7615 0.4059 0.1647 0.112 Uiso 1 1 calc R . . C4 C 0.6243(3) 0.3965(4) 0.0951(3) 0.0937(14) Uani 1 1 d . . . H4 H 0.6569 0.3869 0.0511 0.112 Uiso 1 1 calc R . . C6 C 0.6401(3) 0.4235(3) 0.2271(3) 0.0772(12) Uani 1 1 d . . . H6 H 0.6825 0.4327 0.2727 0.093 Uiso 1 1 calc R . . C21 C 0.3108(5) 0.6593(3) 0.2345(3) 0.0977(17) Uani 1 1 d . . . H21 H 0.3311 0.7189 0.2231 0.117 Uiso 1 1 calc R . . C19 C 0.2211(4) 0.5576(4) 0.3101(3) 0.0915(14) Uani 1 1 d . . . H19 H 0.1808 0.5476 0.3505 0.110 Uiso 1 1 calc R . . C20 C 0.2513(5) 0.6442(4) 0.2943(4) 0.1095(19) Uani 1 1 d . . . H20 H 0.2321 0.6933 0.3236 0.131 Uiso 1 1 calc R . . O3 O 0.03440(17) 0.93915(13) 0.39904(11) 0.0494(5) Uani 1 1 d . . . O1 O 0.0841(2) 0.73674(16) -0.06553(12) 0.0714(7) Uani 1 1 d . . . H1A H 0.0798 0.6809 -0.0595 0.107 Uiso 1 1 calc R . . O2 O 0.05477(17) 0.64035(13) 0.06294(11) 0.0491(5) Uani 1 1 d . . . H2C H 0.0453 0.6189 0.1044 0.074 Uiso 1 1 calc R . . O4 O 0.01465(19) 1.05683(15) 0.32163(11) 0.0548(6) Uani 1 1 d . . . C24 C 0.0267(2) 0.97299(18) 0.33395(14) 0.0377(6) Uani 1 1 d . . . C26 C 0.0403(2) 0.9354(2) 0.19996(16) 0.0460(6) Uani 1 1 d . . . H26 H 0.0360 0.9986 0.1921 0.055 Uiso 1 1 calc R . . C30 C 0.0735(3) 0.7801(2) 0.00061(16) 0.0524(7) Uani 1 1 d . . . C29 C 0.0581(2) 0.73340(18) 0.06732(15) 0.0397(6) Uani 1 1 d . . . C27 C 0.0522(2) 0.87919(19) 0.13335(16) 0.0461(7) Uani 1 1 d . . . C28 C 0.0472(2) 0.78266(19) 0.13234(15) 0.0417(6) Uani 1 1 d . . . H28 H 0.0362 0.7513 0.1765 0.050 Uiso 1 1 calc R . . C25 C 0.0348(2) 0.90741(19) 0.26995(15) 0.0416(6) Uani 1 1 d . . . H25 H 0.0361 0.8446 0.2799 0.050 Uiso 1 1 calc R . . C31 C 0.0781(4) 0.8749(2) 0.0015(2) 0.0731(11) Uani 1 1 d . . . H31 H 0.0879 0.9066 -0.0427 0.088 Uiso 1 1 calc R . . C32 C 0.0683(4) 0.9236(2) 0.0673(2) 0.0679(10) Uani 1 1 d . . . H32 H 0.0726 0.9876 0.0668 0.082 Uiso 1 1 calc R . . O5 O 0.5427(5) 0.3407(4) 0.4279(4) 0.167(2) Uani 1 1 d . . . C36 C 0.2809(14) 0.3953(8) 0.5360(13) 0.263(13) Uani 1 1 d . . . H36 H 0.2198 0.4106 0.5591 0.315 Uiso 1 1 calc R . . C33 C 0.4585(6) 0.3578(4) 0.4723(3) 0.1121(18) Uani 1 1 d . . . C37 C 0.2710(10) 0.3697(9) 0.4608(9) 0.214(7) Uani 1 1 d . . . H37 H 0.2045 0.3655 0.4322 0.257 Uiso 1 1 calc R . . C38 C 0.3620(7) 0.3516(6) 0.4321(4) 0.138(2) Uani 1 1 d . . . H38 H 0.3589 0.3337 0.3817 0.166 Uiso 1 1 calc R . . C34 C 0.4694(13) 0.3823(5) 0.5450(4) 0.198(6) Uani 1 1 d . . . H34 H 0.5373 0.3877 0.5715 0.237 Uiso 1 1 calc R . . C35 C 0.3836(16) 0.3986(6) 0.5784(6) 0.232(9) Uani 1 1 d . . . H35 H 0.3896 0.4122 0.6298 0.278 Uiso 1 1 calc R . . C39 C 0.6512(8) 0.3428(7) 0.4630(8) 0.248(7) Uani 1 1 d . . . H39A H 0.7001 0.3381 0.4250 0.372 Uiso 1 1 calc R . . H39B H 0.6627 0.2920 0.4975 0.372 Uiso 1 1 calc R . . H39C H 0.6637 0.3995 0.4902 0.372 Uiso 1 1 calc R . . C1A C 0.5165(4) 0.4260(4) 0.2992(3) 0.1031(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0987(8) 0.0687(7) 0.1130(9) 0.0230(6) -0.0073(7) -0.0246(5) N1 0.0354(11) 0.0420(12) 0.0425(12) 0.0030(9) -0.0034(9) 0.0002(9) N2 0.0448(13) 0.0580(15) 0.0470(14) 0.0130(11) -0.0084(10) -0.0009(11) C9 0.0406(14) 0.0379(14) 0.0398(14) -0.0004(10) 0.0035(10) 0.0013(10) C1 0.0372(13) 0.0404(14) 0.0371(13) 0.0034(10) -0.0039(10) 0.0017(10) C17 0.0456(15) 0.0428(15) 0.0511(16) -0.0035(12) -0.0106(12) 0.0060(12) C14 0.0378(13) 0.0416(14) 0.0472(15) 0.0088(11) -0.0033(11) -0.0018(11) C10 0.0382(14) 0.0484(16) 0.0680(19) 0.0059(14) 0.0108(13) 0.0046(12) C7 0.0542(18) 0.0499(17) 0.067(2) 0.0102(15) -0.0183(15) -0.0092(14) C15 0.0514(16) 0.0540(17) 0.0473(16) -0.0061(13) -0.0025(12) 0.0061(13) C11 0.0462(16) 0.0543(18) 0.083(2) -0.0014(16) 0.0202(16) -0.0070(14) C18 0.0567(19) 0.068(2) 0.062(2) -0.0168(16) 0.0023(15) 0.0071(15) C12 0.073(2) 0.0497(18) 0.074(2) 0.0122(16) 0.0150(17) -0.0088(16) C8 0.0480(16) 0.0495(17) 0.074(2) 0.0162(15) -0.0114(14) -0.0048(13) C2 0.0357(14) 0.0418(14) 0.0552(17) 0.0088(12) -0.0032(12) -0.0029(11) C22 0.069(2) 0.0437(17) 0.078(2) -0.0008(15) -0.0252(17) -0.0045(15) C3 0.0470(18) 0.093(3) 0.070(2) -0.0014(19) 0.0116(16) -0.0085(17) C16 0.0607(19) 0.068(2) 0.0430(16) -0.0041(14) -0.0062(13) 0.0009(15) C13 0.074(2) 0.054(2) 0.089(3) 0.0277(18) -0.0197(19) -0.0043(17) C5 0.0329(17) 0.081(3) 0.161(5) 0.015(3) -0.009(2) -0.0085(17) C4 0.052(2) 0.116(4) 0.117(4) -0.003(3) 0.028(2) -0.007(2) C6 0.054(2) 0.063(2) 0.106(3) 0.014(2) -0.028(2) -0.0123(17) C21 0.116(4) 0.042(2) 0.123(4) -0.015(2) -0.045(3) 0.003(2) C19 0.083(3) 0.099(4) 0.092(3) -0.048(3) 0.006(2) 0.016(2) C20 0.108(4) 0.090(4) 0.123(5) -0.057(3) -0.022(3) 0.027(3) O3 0.0640(13) 0.0452(11) 0.0375(10) -0.0032(8) -0.0024(9) -0.0016(9) O1 0.128(2) 0.0488(12) 0.0428(12) -0.0061(9) 0.0329(13) -0.0097(13) O2 0.0687(13) 0.0387(10) 0.0418(10) -0.0017(8) 0.0142(9) -0.0003(9) O4 0.0785(15) 0.0481(12) 0.0391(11) -0.0014(8) 0.0124(10) -0.0020(10) C24 0.0333(12) 0.0425(15) 0.0374(14) -0.0046(11) 0.0039(10) -0.0047(10) C26 0.0509(16) 0.0415(14) 0.0460(16) -0.0049(12) 0.0069(12) -0.0019(12) C30 0.074(2) 0.0449(16) 0.0412(15) -0.0055(12) 0.0187(14) -0.0041(14) C29 0.0405(13) 0.0386(14) 0.0404(14) -0.0026(11) 0.0054(10) -0.0019(10) C27 0.0514(16) 0.0425(15) 0.0450(15) -0.0065(12) 0.0079(12) -0.0021(12) C28 0.0454(14) 0.0465(15) 0.0337(13) -0.0007(11) 0.0060(11) -0.0028(11) C25 0.0388(13) 0.0391(14) 0.0467(15) -0.0007(11) 0.0029(11) -0.0036(11) C31 0.125(3) 0.0487(19) 0.0513(19) 0.0013(14) 0.036(2) -0.0082(19) C32 0.112(3) 0.0389(16) 0.057(2) -0.0040(14) 0.0290(19) -0.0075(17) O5 0.146(5) 0.159(5) 0.195(5) -0.050(4) 0.014(4) 0.007(4) C36 0.297(19) 0.096(6) 0.44(3) 0.112(13) 0.24(2) 0.083(10) C33 0.160(6) 0.081(3) 0.093(4) 0.000(3) 0.002(4) 0.015(3) C37 0.163(9) 0.191(11) 0.292(15) 0.176(12) 0.041(10) 0.031(8) C38 0.143(6) 0.172(7) 0.099(4) 0.055(4) 0.012(4) 0.004(5) C34 0.438(18) 0.078(4) 0.074(4) -0.002(3) 0.013(7) -0.036(7) C35 0.51(3) 0.082(5) 0.133(8) -0.008(5) 0.164(13) -0.005(10) C39 0.128(7) 0.141(7) 0.45(2) -0.013(10) -0.080(10) -0.011(6) C1A 0.087(3) 0.127(4) 0.093(3) -0.007(3) -0.002(3) -0.022(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 C22 1.684(5) . ? N1 C14 1.332(3) . ? N1 C15 1.381(4) . ? N1 C1 1.499(3) . ? N2 C14 1.314(4) . ? N2 C16 1.349(4) . ? N2 H2A 0.8600 . ? C9 C8 1.375(4) . ? C9 C10 1.395(4) . ? C9 C1 1.546(4) . ? C1 C17 1.538(4) . ? C1 C2 1.543(4) . ? C17 C18 1.395(5) . ? C17 C22 1.405(5) . ? C14 H14 0.9300 . ? C10 C11 1.378(4) . ? C10 H10 0.9300 . ? C7 C1A 1.347(6) . ? C7 C6 1.381(5) . ? C7 C2 1.392(4) . ? C15 C16 1.346(4) . ? C15 H15 0.9300 . ? C11 C12 1.369(5) . ? C11 H11 0.9300 . ? C18 C19 1.378(5) . ? C18 H18 0.9300 . ? C12 C13 1.368(5) . ? C12 H12 0.9300 . ? C8 C13 1.387(5) . ? C8 H8 0.9300 . ? C2 C3 1.378(5) . ? C22 C21 1.397(6) . ? C3 C4 1.400(5) . ? C3 H3 0.9300 . ? C16 H16 0.9300 . ? C13 H13 0.9300 . ? C5 C6 1.354(7) . ? C5 C4 1.379(7) . ? C5 H5 0.9300 . ? C4 H4 0.9300 . ? C6 H6 0.9300 . ? C21 C20 1.378(9) . ? C21 H21 0.9300 . ? C19 C20 1.352(9) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? O3 C24 1.252(3) . ? O1 C30 1.353(3) . ? O1 H1A 0.8200 . ? O2 C29 1.354(3) . ? O2 H2C 0.8200 . ? O4 C24 1.244(3) . ? C24 C25 1.496(4) . ? C26 C25 1.318(4) . ? C26 C27 1.459(4) . ? C26 H26 0.9300 . ? C30 C31 1.379(5) . ? C30 C29 1.397(4) . ? C29 C28 1.379(4) . ? C27 C32 1.373(4) . ? C27 C28 1.404(4) . ? C28 H28 0.9300 . ? C25 H25 0.9300 . ? C31 C32 1.385(5) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? O5 C33 1.404(8) . ? O5 C39 1.433(9) . ? C36 C37 1.38(2) . ? C36 C35 1.42(2) . ? C36 H36 0.9300 . ? C33 C34 1.335(9) . ? C33 C38 1.339(10) . ? C37 C38 1.321(14) . ? C37 H37 0.9300 . ? C38 H38 0.9300 . ? C34 C35 1.300(18) . ? C34 H34 0.9300 . ? C35 H35 0.9300 . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 N1 C15 107.7(2) . . ? C14 N1 C1 126.8(2) . . ? C15 N1 C1 124.8(2) . . ? C14 N2 C16 109.2(2) . . ? C14 N2 H2A 125.4 . . ? C16 N2 H2A 125.4 . . ? C8 C9 C10 117.5(3) . . ? C8 C9 C1 123.2(2) . . ? C10 C9 C1 119.3(2) . . ? N1 C1 C17 108.2(2) . . ? N1 C1 C2 110.9(2) . . ? C17 C1 C2 109.1(2) . . ? N1 C1 C9 104.5(2) . . ? C17 C1 C9 112.7(2) . . ? C2 C1 C9 111.4(2) . . ? C18 C17 C22 116.5(3) . . ? C18 C17 C1 120.7(3) . . ? C22 C17 C1 122.7(3) . . ? N2 C14 N1 108.8(3) . . ? N2 C14 H14 125.6 . . ? N1 C14 H14 125.6 . . ? C11 C10 C9 121.0(3) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C1A C7 C6 101.3(4) . . ? C1A C7 C2 136.7(4) . . ? C6 C7 C2 121.0(4) . . ? C16 C15 N1 106.7(3) . . ? C16 C15 H15 126.7 . . ? N1 C15 H15 126.7 . . ? C12 C11 C10 120.8(3) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C19 C18 C17 121.9(4) . . ? C19 C18 H18 119.1 . . ? C17 C18 H18 119.1 . . ? C13 C12 C11 118.9(3) . . ? C13 C12 H12 120.6 . . ? C11 C12 H12 120.6 . . ? C9 C8 C13 121.1(3) . . ? C9 C8 H8 119.5 . . ? C13 C8 H8 119.5 . . ? C3 C2 C7 118.8(3) . . ? C3 C2 C1 123.5(3) . . ? C7 C2 C1 117.7(3) . . ? C21 C22 C17 120.8(4) . . ? C21 C22 Cl1 115.5(4) . . ? C17 C22 Cl1 123.6(3) . . ? C2 C3 C4 119.5(4) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C15 C16 N2 107.6(3) . . ? C15 C16 H16 126.2 . . ? N2 C16 H16 126.2 . . ? C12 C13 C8 120.8(3) . . ? C12 C13 H13 119.6 . . ? C8 C13 H13 119.6 . . ? C6 C5 C4 120.2(4) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C4 C3 120.4(4) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C5 C6 C7 120.0(4) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C20 C21 C22 120.3(4) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C20 C19 C18 121.0(5) . . ? C20 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C19 C20 C21 119.6(4) . . ? C19 C20 H20 120.2 . . ? C21 C20 H20 120.2 . . ? C30 O1 H1A 109.5 . . ? C29 O2 H2C 109.5 . . ? O4 C24 O3 122.9(2) . . ? O4 C24 C25 120.4(2) . . ? O3 C24 C25 116.7(2) . . ? C25 C26 C27 127.9(3) . . ? C25 C26 H26 116.0 . . ? C27 C26 H26 116.0 . . ? O1 C30 C31 117.8(3) . . ? O1 C30 C29 123.2(3) . . ? C31 C30 C29 119.0(3) . . ? O2 C29 C28 124.1(2) . . ? O2 C29 C30 116.2(2) . . ? C28 C29 C30 119.7(2) . . ? C32 C27 C28 118.0(3) . . ? C32 C27 C26 117.9(3) . . ? C28 C27 C26 124.1(3) . . ? C29 C28 C27 121.4(2) . . ? C29 C28 H28 119.3 . . ? C27 C28 H28 119.3 . . ? C26 C25 C24 122.5(3) . . ? C26 C25 H25 118.8 . . ? C24 C25 H25 118.8 . . ? C30 C31 C32 120.9(3) . . ? C30 C31 H31 119.6 . . ? C32 C31 H31 119.6 . . ? C27 C32 C31 121.1(3) . . ? C27 C32 H32 119.4 . . ? C31 C32 H32 119.4 . . ? C33 O5 C39 118.8(8) . . ? C37 C36 C35 120.5(13) . . ? C37 C36 H36 119.8 . . ? C35 C36 H36 119.8 . . ? C34 C33 C38 122.1(10) . . ? C34 C33 O5 125.9(9) . . ? C38 C33 O5 111.9(6) . . ? C38 C37 C36 115.8(14) . . ? C38 C37 H37 122.1 . . ? C36 C37 H37 122.1 . . ? C37 C38 C33 122.9(10) . . ? C37 C38 H38 118.5 . . ? C33 C38 H38 118.5 . . ? C35 C34 C33 119.1(13) . . ? C35 C34 H34 120.5 . . ? C33 C34 H34 120.5 . . ? C34 C35 C36 119.6(12) . . ? C34 C35 H35 120.2 . . ? C36 C35 H35 120.2 . . ? O5 C39 H39A 109.5 . . ? O5 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? O5 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.489 _refine_diff_density_min -0.599 _refine_diff_density_rms 0.072