# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_1b _database_code_depnum_ccdc_archive 'CCDC 887543' #TrackingRef '1b_4_deposit bks-vit-ums4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 7-(2-methoxybenzylidene)-5-benzyl-3,3a,4,5,6,7-hexahydro- 3-(2-methoxyphenyl)-2-phenyl-2H-pyrazolo[4,3-c]pyridine ; _chemical_name_common ? _chemical_melting_point 183-185 _chemical_formula_moiety ? _chemical_formula_sum 'C34 H33 N3 O2' _chemical_formula_weight 515.63 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' 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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 14.9779(8) _cell_length_b 14.9860(8) _cell_length_c 15.5420(9) _cell_angle_alpha 67.173(5) _cell_angle_beta 88.293(4) _cell_angle_gamma 62.667(5) _cell_volume 2809.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7106 _cell_measurement_theta_min 2.6391 _cell_measurement_theta_max 29.2092 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.219 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_T_min 0.80907 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_detector_area_resol_mean 15.9821 _diffrn_measurement_method '\w scans' _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 22876 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_sigmaI/netI 0.0567 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 26.00 _reflns_number_total 11037 _reflns_number_gt 7218 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_structure_solution ? _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^)+(0.0425P)^2^+0.4372P] 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 11037 _refine_ls_number_parameters 707 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0930 _refine_ls_R_factor_gt 0.0529 _refine_ls_wR_factor_ref 0.1232 _refine_ls_wR_factor_gt 0.1047 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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 C3A C 0.63802(14) 0.62515(14) 1.02378(11) 0.0337(4) Uani 1 1 d . . . H3A H 0.7120 0.5968 1.0313 0.040 Uiso 1 1 calc R . . C3B C 0.86836(14) 0.34278(14) 0.62233(12) 0.0333(4) Uani 1 1 d . . . H3B H 0.7941 0.3732 0.6161 0.040 Uiso 1 1 calc R . . C3AA C 0.60769(14) 0.57325(14) 0.96933(12) 0.0337(4) Uani 1 1 d . . . H3AA H 0.5532 0.5584 0.9958 0.040 Uiso 1 1 calc R . . C3AB C 0.89426(14) 0.40373(14) 0.52846(12) 0.0340(4) Uani 1 1 d . . . H3AB H 0.9470 0.4202 0.5422 0.041 Uiso 1 1 calc R . . C4A C 0.69049(15) 0.47063(15) 0.96132(13) 0.0416(5) Uani 1 1 d . . . H4A1 H 0.7449 0.4841 0.9350 0.050 Uiso 1 1 calc R . . H4A2 H 0.7192 0.4089 1.0235 0.050 Uiso 1 1 calc R . . C4B C 0.80783(14) 0.50748(14) 0.45236(12) 0.0393(5) Uani 1 1 d . . . H4B1 H 0.7566 0.4914 0.4358 0.047 Uiso 1 1 calc R . . H4B2 H 0.7756 0.5649 0.4751 0.047 Uiso 1 1 calc R . . C6A C 0.61179(15) 0.53054(14) 0.80121(12) 0.0388(5) Uani 1 1 d . . . H6A1 H 0.5752 0.5143 0.7641 0.047 Uiso 1 1 calc R . . H6A2 H 0.6724 0.5260 0.7748 0.047 Uiso 1 1 calc R . . C6B C 0.88955(15) 0.46584(15) 0.32559(12) 0.0403(5) Uani 1 1 d . . . H6B1 H 0.9258 0.4887 0.2763 0.048 Uiso 1 1 calc R . . H6B2 H 0.8311 0.4702 0.2953 0.048 Uiso 1 1 calc R . . C7A C 0.54483(13) 0.64760(15) 0.79028(12) 0.0343(4) Uani 1 1 d . . . C7B C 0.95944(14) 0.34660(15) 0.39346(12) 0.0357(4) Uani 1 1 d . . . C7AA C 0.56463(13) 0.66633(14) 0.87174(12) 0.0334(4) Uani 1 1 d . . . C7AB C 0.93858(13) 0.31761(14) 0.49025(12) 0.0349(4) Uani 1 1 d . . . C8A C 0.60847(14) 0.82208(15) 0.96272(12) 0.0348(4) Uani 1 1 d . . . C8B C 0.88691(14) 0.15112(15) 0.68598(13) 0.0375(5) Uani 1 1 d . . . C9A C 0.67389(15) 0.79595(16) 1.04044(13) 0.0429(5) Uani 1 1 d . . . H9A H 0.7061 0.7242 1.0881 0.051 Uiso 1 1 calc R . . C9B C 0.82554(16) 0.17065(17) 0.75238(14) 0.0477(5) Uani 1 1 d . . . H9B H 0.8004 0.2377 0.7571 0.057 Uiso 1 1 calc R . . C10A C 0.69135(16) 0.87582(17) 1.04734(15) 0.0491(5) Uani 1 1 d . . . H10A H 0.7347 0.8575 1.1002 0.059 Uiso 1 1 calc R . . C10B C 0.80139(18) 0.09188(19) 0.81130(16) 0.0621(6) Uani 1 1 d . . . H10B H 0.7606 0.1061 0.8557 0.075 Uiso 1 1 calc R . . C11A C 0.64587(17) 0.98144(18) 0.97769(16) 0.0550(6) Uani 1 1 d . . . H11A H 0.6581 1.0348 0.9827 0.066 Uiso 1 1 calc R . . C11B C 0.8366(2) -0.0072(2) 0.80528(18) 0.0723(7) Uani 1 1 d . . . H11B H 0.8198 -0.0599 0.8449 0.087 Uiso 1 1 calc R . . C12A C 0.58149(17) 1.00773(17) 0.89974(15) 0.0554(6) Uani 1 1 d . . . H12A H 0.5507 1.0793 0.8518 0.067 Uiso 1 1 calc R . . C12B C 0.89741(19) -0.02720(18) 0.73952(18) 0.0648(7) Uani 1 1 d . . . H12B H 0.9217 -0.0943 0.7351 0.078 Uiso 1 1 calc R . . C13A C 0.56211(16) 0.92981(15) 0.89190(13) 0.0449(5) Uani 1 1 d . . . H13A H 0.5180 0.9490 0.8392 0.054 Uiso 1 1 calc R . . C13B C 0.92300(16) 0.05039(16) 0.67995(14) 0.0480(5) Uani 1 1 d . . . H13B H 0.9642 0.0354 0.6360 0.058 Uiso 1 1 calc R . . C14A C 0.60641(14) 0.60479(15) 1.12019(12) 0.0362(4) Uani 1 1 d . . . C14B C 0.90902(13) 0.34865(15) 0.70736(12) 0.0336(4) Uani 1 1 d . . . C15A C 0.65671(16) 0.49861(16) 1.19344(13) 0.0421(5) Uani 1 1 d . . . C15B C 0.86962(14) 0.45127(15) 0.71105(12) 0.0366(4) Uani 1 1 d . . . C16A C 0.62727(19) 0.4763(2) 1.28181(14) 0.0568(6) Uani 1 1 d . . . H16A H 0.6609 0.4050 1.3302 0.068 Uiso 1 1 calc R . . C16B C 0.90688(17) 0.46138(19) 0.78505(14) 0.0531(6) Uani 1 1 d . . . H16B H 0.8807 0.5303 0.7864 0.064 Uiso 1 1 calc R . . C17A C 0.5480(2) 0.5604(2) 1.29719(16) 0.0639(7) Uani 1 1 d . . . H17A H 0.5281 0.5457 1.3562 0.077 Uiso 1 1 calc R . . C17B C 0.98309(19) 0.3685(2) 0.85670(16) 0.0638(7) Uani 1 1 d . . . H17B H 1.0083 0.3750 0.9066 0.077 Uiso 1 1 calc R . . C18A C 0.49848(18) 0.6652(2) 1.22660(16) 0.0593(6) Uani 1 1 d . . . H18A H 0.4454 0.7219 1.2375 0.071 Uiso 1 1 calc R . . C18B C 1.02218(17) 0.2668(2) 0.85549(15) 0.0596(6) Uani 1 1 d . . . H18B H 1.0731 0.2045 0.9046 0.071 Uiso 1 1 calc R . . C19A C 0.52779(15) 0.68671(18) 1.13858(14) 0.0465(5) Uani 1 1 d . . . H19A H 0.4935 0.7582 1.0907 0.056 Uiso 1 1 calc R . . C19B C 0.98546(15) 0.25692(17) 0.78051(13) 0.0461(5) Uani 1 1 d . . . H19B H 1.0126 0.1878 0.7795 0.055 Uiso 1 1 calc R . . C20A C 0.71535(16) 0.33888(15) 0.89757(13) 0.0450(5) Uani 1 1 d . . . H20A H 0.7753 0.3427 0.8754 0.054 Uiso 1 1 calc R . . H20B H 0.6833 0.3280 0.8519 0.054 Uiso 1 1 calc R . . C20B C 0.77850(16) 0.65322(15) 0.29702(13) 0.0485(5) Uani 1 1 d . . . H20C H 0.7203 0.6492 0.2770 0.058 Uiso 1 1 calc R . . H20D H 0.8100 0.6721 0.2422 0.058 Uiso 1 1 calc R . . C21A C 0.74938(15) 0.23993(15) 0.99113(13) 0.0413(5) Uani 1 1 d . . . C21B C 0.74153(15) 0.74354(15) 0.33073(13) 0.0422(5) Uani 1 1 d . . . C22A C 0.68119(17) 0.21970(18) 1.04609(15) 0.0542(6) Uani 1 1 d . . . H22A H 0.6119 0.2707 1.0262 0.065 Uiso 1 1 calc R . . C22B C 0.64127(19) 0.8022(2) 0.33286(17) 0.0740(8) Uani 1 1 d . . . H22B H 0.5945 0.7851 0.3150 0.089 Uiso 1 1 calc R . . C23A C 0.7129(2) 0.12619(19) 1.12945(17) 0.0673(7) Uani 1 1 d . . . H23A H 0.6652 0.1141 1.1650 0.081 Uiso 1 1 calc R . . C23B C 0.6075(2) 0.8882(3) 0.3616(2) 0.1055(12) Uani 1 1 d . . . H23B H 0.5386 0.9282 0.3629 0.127 Uiso 1 1 calc R . . C24A C 0.8145(2) 0.0510(2) 1.16008(18) 0.0811(8) Uani 1 1 d . . . H24A H 0.8363 -0.0125 1.2165 0.097 Uiso 1 1 calc R . . C24B C 0.6765(3) 0.9133(2) 0.3879(2) 0.1004(12) Uani 1 1 d . . . H24B H 0.6544 0.9715 0.4057 0.121 Uiso 1 1 calc R . . C25A C 0.8837(2) 0.0694(2) 1.1076(2) 0.0890(9) Uani 1 1 d . . . H25A H 0.9530 0.0187 1.1286 0.107 Uiso 1 1 calc R . . C25B C 0.7762(3) 0.8535(2) 0.38771(19) 0.0882(9) Uani 1 1 d . . . H25B H 0.8232 0.8692 0.4073 0.106 Uiso 1 1 calc R . . C26A C 0.85137(17) 0.16344(19) 1.02295(17) 0.0674(7) Uani 1 1 d . . . H26A H 0.8992 0.1749 0.9873 0.081 Uiso 1 1 calc R . . C26B C 0.80883(19) 0.7701(2) 0.35912(16) 0.0633(6) Uani 1 1 d . . . H26B H 0.8780 0.7302 0.3588 0.076 Uiso 1 1 calc R . . C27A C 0.47628(14) 0.73117(15) 0.71231(12) 0.0398(5) Uani 1 1 d . . . H27A H 0.4390 0.7988 0.7160 0.048 Uiso 1 1 calc R . . C27B C 1.03307(14) 0.27136(15) 0.36926(13) 0.0399(5) Uani 1 1 d . . . H27B H 1.0706 0.2008 0.4179 0.048 Uiso 1 1 calc R . . C28A C 0.45273(15) 0.72948(15) 0.62206(13) 0.0395(5) Uani 1 1 d . . . C28B C 1.06202(14) 0.28623(15) 0.27582(13) 0.0382(5) Uani 1 1 d . . . C29A C 0.35316(16) 0.80095(16) 0.56795(13) 0.0457(5) Uani 1 1 d . . . C29B C 1.16436(15) 0.22639(16) 0.26923(14) 0.0425(5) Uani 1 1 d . . . C30A C 0.32883(19) 0.8000(2) 0.48293(16) 0.0663(7) Uani 1 1 d . . . H30A H 0.2628 0.8471 0.4480 0.080 Uiso 1 1 calc R . . C30B C 1.19468(17) 0.24185(19) 0.18185(16) 0.0558(6) Uani 1 1 d . . . H30B H 1.2632 0.2034 0.1786 0.067 Uiso 1 1 calc R . . C31A C 0.4016(2) 0.7300(2) 0.45028(17) 0.0776(8) Uani 1 1 d . . . H31A H 0.3843 0.7289 0.3939 0.093 Uiso 1 1 calc R . . C31B C 1.12296(19) 0.3143(2) 0.10002(16) 0.0660(7) Uani 1 1 d . . . H31B H 1.1433 0.3251 0.0414 0.079 Uiso 1 1 calc R . . C32A C 0.49953(19) 0.6617(2) 0.49988(15) 0.0685(7) Uani 1 1 d . . . H32A H 0.5492 0.6155 0.4768 0.082 Uiso 1 1 calc R . . C32B C 1.02196(19) 0.3707(2) 0.10411(15) 0.0606(6) Uani 1 1 d . . . H32B H 0.9736 0.4181 0.0485 0.073 Uiso 1 1 calc R . . C33A C 0.52367(16) 0.66213(17) 0.58464(13) 0.0501(5) Uani 1 1 d . . . H33A H 0.5904 0.6152 0.6181 0.060 Uiso 1 1 calc R . . C33B C 0.99195(16) 0.35694(17) 0.19109(14) 0.0472(5) Uani 1 1 d . . . H33B H 0.9231 0.3959 0.1931 0.057 Uiso 1 1 calc R . . C34A C 0.7756(2) 0.30736(18) 1.23261(17) 0.0778(8) Uani 1 1 d . . . H34A H 0.7209 0.2899 1.2408 0.117 Uiso 1 1 calc R . . H34B H 0.8075 0.2918 1.2931 0.117 Uiso 1 1 calc R . . H34C H 0.8252 0.2633 1.2050 0.117 Uiso 1 1 calc R . . C34B C 0.76663(19) 0.64725(16) 0.62257(17) 0.0621(6) Uani 1 1 d . . . H34D H 0.8270 0.6549 0.6176 0.093 Uiso 1 1 calc R . . H34E H 0.7380 0.6616 0.6749 0.093 Uiso 1 1 calc R . . H34F H 0.7175 0.6992 0.5649 0.093 Uiso 1 1 calc R . . C35A C 0.18218(18) 0.9372(2) 0.55651(18) 0.0782(8) Uani 1 1 d . . . H35A H 0.1556 0.8931 0.5484 0.117 Uiso 1 1 calc R . . H35B H 0.1798 0.9901 0.4955 0.117 Uiso 1 1 calc R . . H35C H 0.1417 0.9756 0.5925 0.117 Uiso 1 1 calc R . . C35B C 1.33391(18) 0.0849(2) 0.3516(2) 0.0868(9) Uani 1 1 d . . . H35D H 1.3637 0.1303 0.3183 0.130 Uiso 1 1 calc R . . H35E H 1.3364 0.0406 0.3195 0.130 Uiso 1 1 calc R . . H35F H 1.3715 0.0373 0.4153 0.130 Uiso 1 1 calc R . . N1A N 0.55515(12) 0.75840(12) 0.86591(10) 0.0381(4) Uani 1 1 d . . . N1B N 0.94708(12) 0.22325(12) 0.54535(10) 0.0421(4) Uani 1 1 d . . . N2A N 0.58482(12) 0.74378(12) 0.95691(10) 0.0384(4) Uani 1 1 d . . . N2B N 0.91608(12) 0.22845(12) 0.62980(10) 0.0416(4) Uani 1 1 d . . . N5A N 0.64382(12) 0.44518(12) 0.89915(10) 0.0384(4) Uani 1 1 d . . . N5B N 0.85250(12) 0.54388(12) 0.36988(10) 0.0394(4) Uani 1 1 d . . . O1A O 0.73605(11) 0.42194(11) 1.17134(9) 0.0534(4) Uani 1 1 d . . . O1B O 0.79232(10) 0.53745(10) 0.63784(9) 0.0437(3) Uani 1 1 d . . . O2A O 0.28506(11) 0.86752(12) 0.60564(10) 0.0589(4) Uani 1 1 d . . . O2B O 1.23010(11) 0.15379(12) 0.35408(10) 0.0578(4) 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 C3A 0.0392(11) 0.0309(10) 0.0276(9) -0.0102(8) 0.0041(8) -0.0160(9) C3B 0.0386(11) 0.0282(9) 0.0317(10) -0.0143(8) 0.0105(8) -0.0140(9) C3AA 0.0398(11) 0.0322(10) 0.0277(9) -0.0129(8) 0.0048(8) -0.0162(9) C3AB 0.0397(11) 0.0316(10) 0.0277(9) -0.0126(8) 0.0095(8) -0.0153(9) C4A 0.0463(12) 0.0356(11) 0.0327(10) -0.0131(8) -0.0013(9) -0.0127(10) C4B 0.0458(12) 0.0322(10) 0.0318(10) -0.0146(8) 0.0108(8) -0.0119(9) C6A 0.0439(12) 0.0393(11) 0.0305(10) -0.0164(8) 0.0035(8) -0.0165(10) C6B 0.0459(12) 0.0414(11) 0.0299(10) -0.0157(9) 0.0129(8) -0.0182(10) C7A 0.0359(10) 0.0374(10) 0.0282(10) -0.0129(8) 0.0051(8) -0.0174(9) C7B 0.0403(11) 0.0346(10) 0.0317(10) -0.0156(8) 0.0113(8) -0.0168(9) C7AA 0.0335(10) 0.0306(10) 0.0298(10) -0.0125(8) 0.0039(8) -0.0107(9) C7AB 0.0368(11) 0.0299(10) 0.0321(10) -0.0137(8) 0.0109(8) -0.0113(9) C8A 0.0410(11) 0.0346(10) 0.0319(10) -0.0172(8) 0.0135(8) -0.0186(9) C8B 0.0442(11) 0.0305(10) 0.0333(10) -0.0097(8) 0.0038(8) -0.0175(9) C9A 0.0519(13) 0.0392(11) 0.0364(11) -0.0133(9) 0.0053(9) -0.0232(10) C9B 0.0612(14) 0.0419(12) 0.0462(12) -0.0201(10) 0.0206(10) -0.0291(11) C10A 0.0547(13) 0.0547(14) 0.0480(13) -0.0235(11) 0.0106(10) -0.0329(12) C10B 0.0765(17) 0.0592(15) 0.0635(15) -0.0268(12) 0.0306(12) -0.0430(14) C11A 0.0696(16) 0.0549(14) 0.0614(15) -0.0300(12) 0.0200(12) -0.0421(13) C11B 0.091(2) 0.0615(16) 0.0781(18) -0.0212(14) 0.0297(15) -0.0550(16) C12A 0.0719(16) 0.0361(12) 0.0538(14) -0.0137(10) 0.0136(12) -0.0272(12) C12B 0.0815(18) 0.0395(13) 0.0789(18) -0.0240(12) 0.0153(14) -0.0344(13) C13A 0.0557(13) 0.0380(11) 0.0371(11) -0.0152(9) 0.0085(9) -0.0204(11) C13B 0.0569(14) 0.0372(11) 0.0492(13) -0.0202(10) 0.0104(10) -0.0208(11) C14A 0.0455(12) 0.0423(11) 0.0297(10) -0.0164(9) 0.0055(8) -0.0271(10) C14B 0.0351(10) 0.0379(10) 0.0278(9) -0.0122(8) 0.0127(8) -0.0194(9) C15A 0.0553(13) 0.0465(12) 0.0333(11) -0.0154(9) 0.0050(9) -0.0324(11) C15B 0.0413(11) 0.0426(11) 0.0328(10) -0.0178(9) 0.0120(8) -0.0244(10) C16A 0.0880(18) 0.0657(15) 0.0313(11) -0.0103(11) 0.0070(11) -0.0566(15) C16B 0.0683(15) 0.0664(15) 0.0449(13) -0.0301(11) 0.0148(11) -0.0430(13) C17A 0.099(2) 0.095(2) 0.0449(14) -0.0425(14) 0.0353(13) -0.0735(18) C17B 0.0726(17) 0.096(2) 0.0436(13) -0.0321(14) 0.0096(12) -0.0548(16) C18A 0.0715(16) 0.0809(18) 0.0550(15) -0.0448(14) 0.0303(12) -0.0476(15) C18B 0.0480(14) 0.0783(18) 0.0375(12) -0.0101(12) -0.0011(10) -0.0303(14) C19A 0.0561(13) 0.0545(13) 0.0400(12) -0.0259(10) 0.0138(10) -0.0307(12) C19B 0.0429(12) 0.0474(12) 0.0364(11) -0.0117(9) 0.0092(9) -0.0180(11) C20A 0.0507(13) 0.0377(11) 0.0413(11) -0.0212(9) 0.0086(9) -0.0136(10) C20B 0.0578(14) 0.0381(11) 0.0307(11) -0.0080(9) 0.0038(9) -0.0140(11) C21A 0.0435(12) 0.0322(10) 0.0425(11) -0.0189(9) 0.0049(9) -0.0113(10) C21B 0.0452(12) 0.0290(10) 0.0303(10) -0.0027(8) 0.0020(9) -0.0090(10) C22A 0.0447(13) 0.0456(13) 0.0573(14) -0.0199(11) 0.0113(11) -0.0119(11) C22B 0.0490(15) 0.0710(17) 0.0767(18) -0.0340(15) -0.0032(13) -0.0067(14) C23A 0.0702(17) 0.0510(15) 0.0664(16) -0.0172(13) 0.0261(13) -0.0255(14) C23B 0.071(2) 0.078(2) 0.101(2) -0.0458(19) -0.0031(18) 0.0227(18) C24A 0.084(2) 0.0458(14) 0.0626(16) 0.0012(12) 0.0159(15) -0.0124(15) C24B 0.153(3) 0.0413(16) 0.0657(19) -0.0221(14) -0.004(2) -0.015(2) C25A 0.0533(16) 0.0619(17) 0.0805(19) 0.0068(15) 0.0051(14) -0.0028(15) C25B 0.133(3) 0.073(2) 0.077(2) -0.0328(16) 0.0175(19) -0.063(2) C26A 0.0462(14) 0.0568(15) 0.0671(16) -0.0090(13) 0.0119(12) -0.0143(13) C26B 0.0635(16) 0.0655(16) 0.0622(15) -0.0263(13) 0.0172(12) -0.0331(14) C27A 0.0446(12) 0.0370(11) 0.0359(11) -0.0152(9) 0.0019(9) -0.0182(10) C27B 0.0459(12) 0.0356(11) 0.0382(11) -0.0168(9) 0.0150(9) -0.0192(10) C28A 0.0479(12) 0.0379(11) 0.0303(10) -0.0084(8) 0.0008(9) -0.0235(10) C28B 0.0464(12) 0.0377(11) 0.0412(11) -0.0246(9) 0.0202(9) -0.0230(10) C29A 0.0501(13) 0.0390(11) 0.0371(11) -0.0088(9) -0.0016(10) -0.0187(11) C29B 0.0494(13) 0.0393(11) 0.0468(12) -0.0264(10) 0.0169(10) -0.0215(10) C30A 0.0630(16) 0.0714(16) 0.0453(13) -0.0170(12) -0.0154(12) -0.0228(14) C30B 0.0563(14) 0.0644(15) 0.0617(15) -0.0416(13) 0.0343(12) -0.0300(13) C31A 0.0817(19) 0.098(2) 0.0456(14) -0.0381(14) -0.0026(13) -0.0304(17) C31B 0.0787(18) 0.0837(18) 0.0442(14) -0.0365(13) 0.0330(13) -0.0395(16) C32A 0.0687(17) 0.0875(18) 0.0451(13) -0.0359(13) 0.0090(12) -0.0283(15) C32B 0.0695(16) 0.0738(16) 0.0403(13) -0.0310(12) 0.0173(11) -0.0309(14) C33A 0.0514(13) 0.0576(14) 0.0354(11) -0.0179(10) 0.0030(9) -0.0230(12) C33B 0.0502(13) 0.0541(13) 0.0443(12) -0.0295(10) 0.0174(10) -0.0243(11) C34A 0.099(2) 0.0405(13) 0.0699(17) -0.0046(12) -0.0047(15) -0.0301(14) C34B 0.0783(17) 0.0393(12) 0.0729(16) -0.0248(11) 0.0136(13) -0.0307(13) C35A 0.0531(16) 0.0599(16) 0.0848(19) -0.0183(14) -0.0088(14) -0.0079(14) C35B 0.0492(16) 0.0811(19) 0.095(2) -0.0422(17) 0.0156(14) -0.0010(15) N1A 0.0457(10) 0.0369(9) 0.0273(8) -0.0130(7) 0.0035(7) -0.0171(8) N1B 0.0532(10) 0.0344(9) 0.0353(9) -0.0168(7) 0.0174(8) -0.0175(8) N2A 0.0547(10) 0.0326(8) 0.0258(8) -0.0104(7) 0.0029(7) -0.0209(8) N2B 0.0605(11) 0.0295(8) 0.0338(9) -0.0159(7) 0.0211(8) -0.0198(8) N5A 0.0460(10) 0.0318(8) 0.0306(8) -0.0151(7) 0.0029(7) -0.0119(8) N5B 0.0480(10) 0.0300(8) 0.0271(8) -0.0096(7) 0.0090(7) -0.0111(8) O1A 0.0637(10) 0.0378(8) 0.0417(8) -0.0050(7) -0.0003(7) -0.0207(8) O1B 0.0545(9) 0.0318(7) 0.0441(8) -0.0190(6) 0.0058(7) -0.0177(7) O2A 0.0503(9) 0.0484(9) 0.0532(9) -0.0161(7) -0.0071(7) -0.0083(8) O2B 0.0487(9) 0.0534(9) 0.0596(10) -0.0286(8) 0.0178(7) -0.0124(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 C3A N2A 1.480(2) . ? C3A C14A 1.516(2) . ? C3A C3AA 1.544(2) . ? C3A H3A 0.9800 . ? C3B N2B 1.479(2) . ? C3B C14B 1.521(2) . ? C3B C3AB 1.540(2) . ? C3B H3B 0.9800 . ? C3AA C7AA 1.501(2) . ? C3AA C4A 1.519(2) . ? C3AA H3AA 0.9800 . ? C3AB C7AB 1.498(2) . ? C3AB C4B 1.519(2) . ? C3AB H3AB 0.9800 . ? C4A N5A 1.463(2) . ? C4A H4A1 0.9700 . ? C4A H4A2 0.9700 . ? C4B N5B 1.459(2) . ? C4B H4B1 0.9700 . ? C4B H4B2 0.9700 . ? C6A N5A 1.467(2) . ? C6A C7A 1.508(2) . ? C6A H6A1 0.9700 . ? C6A H6A2 0.9700 . ? C6B N5B 1.468(2) . ? C6B C7B 1.512(2) . ? C6B H6B1 0.9700 . ? C6B H6B2 0.9700 . ? C7A C27A 1.344(2) . ? C7A C7AA 1.464(2) . ? C7B C27B 1.338(2) . ? C7B C7AB 1.462(2) . ? C7AA N1A 1.287(2) . ? C7AB N1B 1.285(2) . ? C8A C9A 1.387(2) . ? C8A C13A 1.392(2) . ? C8A N2A 1.406(2) . ? C8B C9B 1.388(3) . ? C8B C13B 1.392(3) . ? C8B N2B 1.398(2) . ? C9A C10A 1.379(3) . ? C9A H9A 0.9300 . ? C9B C10B 1.377(3) . ? C9B H9B 0.9300 . ? C10A C11A 1.366(3) . ? C10A H10A 0.9300 . ? C10B C11B 1.369(3) . ? C10B H10B 0.9300 . ? C11A C12A 1.380(3) . ? C11A H11A 0.9300 . ? C11B C12B 1.377(3) . ? C11B H11B 0.9300 . ? C12A C13A 1.373(3) . ? C12A H12A 0.9300 . ? C12B C13B 1.382(3) . ? C12B H12B 0.9300 . ? C13A H13A 0.9300 . ? C13B H13B 0.9300 . ? C14A C19A 1.378(3) . ? C14A C15A 1.393(3) . ? C14B C19B 1.383(2) . ? C14B C15B 1.396(2) . ? C15A O1A 1.371(2) . ? C15A C16A 1.391(3) . ? C15B O1B 1.367(2) . ? C15B C16B 1.381(3) . ? C16A C17A 1.378(3) . ? C16A H16A 0.9300 . ? C16B C17B 1.377(3) . ? C16B H16B 0.9300 . ? C17A C18A 1.365(3) . ? C17A H17A 0.9300 . ? C17B C18B 1.366(3) . ? C17B H17B 0.9300 . ? C18A C19A 1.386(3) . ? C18A H18A 0.9300 . ? C18B C19B 1.389(3) . ? C18B H18B 0.9300 . ? C19A H19A 0.9300 . ? C19B H19B 0.9300 . ? C20A N5A 1.466(2) . ? C20A C21A 1.500(3) . ? C20A H20A 0.9700 . ? C20A H20B 0.9700 . ? C20B N5B 1.471(2) . ? C20B C21B 1.503(3) . ? C20B H20C 0.9700 . ? C20B H20D 0.9700 . ? C21A C26A 1.375(3) . ? C21A C22A 1.377(3) . ? C21B C22B 1.355(3) . ? C21B C26B 1.378(3) . ? C22A C23A 1.373(3) . ? C22A H22A 0.9300 . ? C22B C23B 1.396(4) . ? C22B H22B 0.9300 . ? C23A C24A 1.366(3) . ? C23A H23A 0.9300 . ? C23B C24B 1.370(5) . ? C23B H23B 0.9300 . ? C24A C25A 1.361(4) . ? C24A H24A 0.9300 . ? C24B C25B 1.343(4) . ? C24B H24B 0.9300 . ? C25A C26A 1.387(3) . ? C25A H25A 0.9300 . ? C25B C26B 1.362(3) . ? C25B H25B 0.9300 . ? C26A H26A 0.9300 . ? C26B H26B 0.9300 . ? C27A C28A 1.469(2) . ? C27A H27A 0.9300 . ? C27B C28B 1.465(3) . ? C27B H27B 0.9300 . ? C28A C33A 1.385(3) . ? C28A C29A 1.410(3) . ? C28B C33B 1.392(3) . ? C28B C29B 1.401(3) . ? C29A O2A 1.365(2) . ? C29A C30A 1.388(3) . ? C29B O2B 1.368(2) . ? C29B C30B 1.386(3) . ? C30A C31A 1.370(3) . ? C30A H30A 0.9300 . ? C30B C31B 1.374(3) . ? C30B H30B 0.9300 . ? C31A C32A 1.367(3) . ? C31A H31A 0.9300 . ? C31B C32B 1.367(3) . ? C31B H31B 0.9300 . ? C32A C33A 1.380(3) . ? C32A H32A 0.9300 . ? C32B C33B 1.380(3) . ? C32B H32B 0.9300 . ? C33A H33A 0.9300 . ? C33B H33B 0.9300 . ? C34A O1A 1.427(2) . ? C34A H34A 0.9600 . ? C34A H34B 0.9600 . ? C34A H34C 0.9600 . ? C34B O1B 1.426(2) . ? C34B H34D 0.9600 . ? C34B H34E 0.9600 . ? C34B H34F 0.9600 . ? C35A O2A 1.422(2) . ? C35A H35A 0.9600 . ? C35A H35B 0.9600 . ? C35A H35C 0.9600 . ? C35B O2B 1.428(3) . ? C35B H35D 0.9600 . ? C35B H35E 0.9600 . ? C35B H35F 0.9600 . ? N1A N2A 1.3976(19) . ? N1B N2B 1.398(2) . ? 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 N2A C3A C14A 112.59(14) . . ? N2A C3A C3AA 101.69(13) . . ? C14A C3A C3AA 113.76(15) . . ? N2A C3A H3A 109.5 . . ? C14A C3A H3A 109.5 . . ? C3AA C3A H3A 109.5 . . ? N2B C3B C14B 112.40(14) . . ? N2B C3B C3AB 102.21(13) . . ? C14B C3B C3AB 113.49(15) . . ? N2B C3B H3B 109.5 . . ? C14B C3B H3B 109.5 . . ? C3AB C3B H3B 109.5 . . ? C7AA C3AA C4A 108.48(14) . . ? C7AA C3AA C3A 101.64(14) . . ? C4A C3AA C3A 118.77(15) . . ? C7AA C3AA H3AA 109.2 . . ? C4A C3AA H3AA 109.2 . . ? C3A C3AA H3AA 109.2 . . ? C7AB C3AB C4B 107.62(14) . . ? C7AB C3AB C3B 101.96(14) . . ? C4B C3AB C3B 118.64(15) . . ? C7AB C3AB H3AB 109.4 . . ? C4B C3AB H3AB 109.4 . . ? C3B C3AB H3AB 109.4 . . ? N5A C4A C3AA 107.78(14) . . ? N5A C4A H4A1 110.2 . . ? C3AA C4A H4A1 110.2 . . ? N5A C4A H4A2 110.2 . . ? C3AA C4A H4A2 110.2 . . ? H4A1 C4A H4A2 108.5 . . ? N5B C4B C3AB 107.16(14) . . ? N5B C4B H4B1 110.3 . . ? C3AB C4B H4B1 110.3 . . ? N5B C4B H4B2 110.3 . . ? C3AB C4B H4B2 110.3 . . ? H4B1 C4B H4B2 108.5 . . ? N5A C6A C7A 115.01(14) . . ? N5A C6A H6A1 108.5 . . ? C7A C6A H6A1 108.5 . . ? N5A C6A H6A2 108.5 . . ? C7A C6A H6A2 108.5 . . ? H6A1 C6A H6A2 107.5 . . ? N5B C6B C7B 114.52(14) . . ? N5B C6B H6B1 108.6 . . ? C7B C6B H6B1 108.6 . . ? N5B C6B H6B2 108.6 . . ? C7B C6B H6B2 108.6 . . ? H6B1 C6B H6B2 107.6 . . ? C27A C7A C7AA 121.05(16) . . ? C27A C7A C6A 124.99(16) . . ? C7AA C7A C6A 113.86(14) . . ? C27B C7B C7AB 121.42(16) . . ? C27B C7B C6B 124.54(17) . . ? C7AB C7B C6B 114.02(15) . . ? N1A C7AA C7A 124.30(16) . . ? N1A C7AA C3AA 114.51(15) . . ? C7A C7AA C3AA 120.97(16) . . ? N1B C7AB C7B 124.66(16) . . ? N1B C7AB C3AB 114.76(15) . . ? C7B C7AB C3AB 120.30(16) . . ? C9A C8A C13A 118.61(18) . . ? C9A C8A N2A 121.28(16) . . ? C13A C8A N2A 120.03(16) . . ? C9B C8B C13B 118.48(19) . . ? C9B C8B N2B 120.75(17) . . ? C13B C8B N2B 120.68(18) . . ? C10A C9A C8A 120.33(18) . . ? C10A C9A H9A 119.8 . . ? C8A C9A H9A 119.8 . . ? C10B C9B C8B 120.7(2) . . ? C10B C9B H9B 119.6 . . ? C8B C9B H9B 119.6 . . ? C11A C10A C9A 120.95(19) . . ? C11A C10A H10A 119.5 . . ? C9A C10A H10A 119.5 . . ? C11B C10B C9B 120.8(2) . . ? C11B C10B H10B 119.6 . . ? C9B C10B H10B 119.6 . . ? C10A C11A C12A 119.0(2) . . ? C10A C11A H11A 120.5 . . ? C12A C11A H11A 120.5 . . ? C10B C11B C12B 118.8(2) . . ? C10B C11B H11B 120.6 . . ? C12B C11B H11B 120.6 . . ? C13A C12A C11A 121.0(2) . . ? C13A C12A H12A 119.5 . . ? C11A C12A H12A 119.5 . . ? C11B C12B C13B 121.3(2) . . ? C11B C12B H12B 119.3 . . ? C13B C12B H12B 119.3 . . ? C12A C13A C8A 120.07(19) . . ? C12A C13A H13A 120.0 . . ? C8A C13A H13A 120.0 . . ? C12B C13B C8B 119.8(2) . . ? C12B C13B H13B 120.1 . . ? C8B C13B H13B 120.1 . . ? C19A C14A C15A 117.89(18) . . ? C19A C14A C3A 122.81(17) . . ? C15A C14A C3A 119.28(17) . . ? C19B C14B C15B 118.25(17) . . ? C19B C14B C3B 122.83(17) . . ? C15B C14B C3B 118.89(15) . . ? O1A C15A C16A 124.33(19) . . ? O1A C15A C14A 114.91(17) . . ? C16A C15A C14A 120.7(2) . . ? O1B C15B C16B 124.07(17) . . ? O1B C15B C14B 114.94(15) . . ? C16B C15B C14B 120.98(18) . . ? C17A C16A C15A 119.6(2) . . ? C17A C16A H16A 120.2 . . ? C15A C16A H16A 120.2 . . ? C17B C16B C15B 119.3(2) . . ? C17B C16B H16B 120.3 . . ? C15B C16B H16B 120.3 . . ? C18A C17A C16A 120.6(2) . . ? C18A C17A H17A 119.7 . . ? C16A C17A H17A 119.7 . . ? C18B C17B C16B 120.9(2) . . ? C18B C17B H17B 119.5 . . ? C16B C17B H17B 119.5 . . ? C17A C18A C19A 119.6(2) . . ? C17A C18A H18A 120.2 . . ? C19A C18A H18A 120.2 . . ? C17B C18B C19B 119.7(2) . . ? C17B C18B H18B 120.1 . . ? C19B C18B H18B 120.1 . . ? C14A C19A C18A 121.7(2) . . ? C14A C19A H19A 119.2 . . ? C18A C19A H19A 119.2 . . ? C14B C19B C18B 120.8(2) . . ? C14B C19B H19B 119.6 . . ? C18B C19B H19B 119.6 . . ? N5A C20A C21A 115.08(16) . . ? N5A C20A H20A 108.5 . . ? C21A C20A H20A 108.5 . . ? N5A C20A H20B 108.5 . . ? C21A C20A H20B 108.5 . . ? H20A C20A H20B 107.5 . . ? N5B C20B C21B 113.25(15) . . ? N5B C20B H20C 108.9 . . ? C21B C20B H20C 108.9 . . ? N5B C20B H20D 108.9 . . ? C21B C20B H20D 108.9 . . ? H20C C20B H20D 107.7 . . ? C26A C21A C22A 117.7(2) . . ? C26A C21A C20A 120.0(2) . . ? C22A C21A C20A 122.24(18) . . ? C22B C21B C26B 118.1(2) . . ? C22B C21B C20B 121.2(2) . . ? C26B C21B C20B 120.7(2) . . ? C23A C22A C21A 121.7(2) . . ? C23A C22A H22A 119.1 . . ? C21A C22A H22A 119.1 . . ? C21B C22B C23B 120.6(3) . . ? C21B C22B H22B 119.7 . . ? C23B C22B H22B 119.7 . . ? C24A C23A C22A 119.9(2) . . ? C24A C23A H23A 120.1 . . ? C22A C23A H23A 120.1 . . ? C24B C23B C22B 119.6(3) . . ? C24B C23B H23B 120.2 . . ? C22B C23B H23B 120.2 . . ? C25A C24A C23A 119.7(2) . . ? C25A C24A H24A 120.2 . . ? C23A C24A H24A 120.2 . . ? C25B C24B C23B 119.8(3) . . ? C25B C24B H24B 120.1 . . ? C23B C24B H24B 120.1 . . ? C24A C25A C26A 120.4(2) . . ? C24A C25A H25A 119.8 . . ? C26A C25A H25A 119.8 . . ? C24B C25B C26B 120.5(3) . . ? C24B C25B H25B 119.7 . . ? C26B C25B H25B 119.7 . . ? C21A C26A C25A 120.7(2) . . ? C21A C26A H26A 119.6 . . ? C25A C26A H26A 119.6 . . ? C25B C26B C21B 121.4(3) . . ? C25B C26B H26B 119.3 . . ? C21B C26B H26B 119.3 . . ? C7A C27A C28A 128.36(18) . . ? C7A C27A H27A 115.8 . . ? C28A C27A H27A 115.8 . . ? C7B C27B C28B 128.16(18) . . ? C7B C27B H27B 115.9 . . ? C28B C27B H27B 115.9 . . ? C33A C28A C29A 116.65(17) . . ? C33A C28A C27A 123.87(17) . . ? C29A C28A C27A 119.47(18) . . ? C33B C28B C29B 117.05(17) . . ? C33B C28B C27B 123.14(17) . . ? C29B C28B C27B 119.80(17) . . ? O2A C29A C30A 123.94(19) . . ? O2A C29A C28A 115.55(17) . . ? C30A C29A C28A 120.5(2) . . ? O2B C29B C30B 123.56(19) . . ? O2B C29B C28B 115.32(17) . . ? C30B C29B C28B 121.11(19) . . ? C31A C30A C29A 120.3(2) . . ? C31A C30A H30A 119.8 . . ? C29A C30A H30A 119.8 . . ? C31B C30B C29B 119.7(2) . . ? C31B C30B H30B 120.2 . . ? C29B C30B H30B 120.2 . . ? C32A C31A C30A 120.6(2) . . ? C32A C31A H31A 119.7 . . ? C30A C31A H31A 119.7 . . ? C32B C31B C30B 120.6(2) . . ? C32B C31B H31B 119.7 . . ? C30B C31B H31B 119.7 . . ? C31A C32A C33A 119.1(2) . . ? C31A C32A H32A 120.4 . . ? C33A C32A H32A 120.4 . . ? C31B C32B C33B 119.8(2) . . ? C31B C32B H32B 120.1 . . ? C33B C32B H32B 120.1 . . ? C32A C33A C28A 122.8(2) . . ? C32A C33A H33A 118.6 . . ? C28A C33A H33A 118.6 . . ? C32B C33B C28B 121.7(2) . . ? C32B C33B H33B 119.1 . . ? C28B C33B H33B 119.1 . . ? O1A C34A H34A 109.5 . . ? O1A C34A H34B 109.5 . . ? H34A C34A H34B 109.5 . . ? O1A C34A H34C 109.5 . . ? H34A C34A H34C 109.5 . . ? H34B C34A H34C 109.5 . . ? O1B C34B H34D 109.5 . . ? O1B C34B H34E 109.5 . . ? H34D C34B H34E 109.5 . . ? O1B C34B H34F 109.5 . . ? H34D C34B H34F 109.5 . . ? H34E C34B H34F 109.5 . . ? O2A C35A H35A 109.5 . . ? O2A C35A H35B 109.5 . . ? H35A C35A H35B 109.5 . . ? O2A C35A H35C 109.5 . . ? H35A C35A H35C 109.5 . . ? H35B C35A H35C 109.5 . . ? O2B C35B H35D 109.5 . . ? O2B C35B H35E 109.5 . . ? H35D C35B H35E 109.5 . . ? O2B C35B H35F 109.5 . . ? H35D C35B H35F 109.5 . . ? H35E C35B H35F 109.5 . . ? C7AA N1A N2A 108.14(14) . . ? C7AB N1B N2B 108.17(14) . . ? N1A N2A C8A 116.74(15) . . ? N1A N2A C3A 111.38(13) . . ? C8A N2A C3A 123.42(14) . . ? C8B N2B N1B 117.34(14) . . ? C8B N2B C3B 122.90(15) . . ? N1B N2B C3B 111.72(14) . . ? C4A N5A C20A 111.24(14) . . ? C4A N5A C6A 111.40(15) . . ? C20A N5A C6A 107.70(14) . . ? C4B N5B C6B 111.82(15) . . ? C4B N5B C20B 111.74(15) . . ? C6B N5B C20B 107.76(13) . . ? C15A O1A C34A 118.48(18) . . ? C15B O1B C34B 117.96(15) . . ? C29A O2A C35A 117.97(17) . . ? C29B O2B C35B 117.68(17) . . ? 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 N2A C3A C3AA C7AA 13.51(18) . . . . ? C14A C3A C3AA C7AA 134.83(15) . . . . ? N2A C3A C3AA C4A 132.35(17) . . . . ? C14A C3A C3AA C4A -106.34(19) . . . . ? N2B C3B C3AB C7AB 8.48(17) . . . . ? C14B C3B C3AB C7AB 129.75(15) . . . . ? N2B C3B C3AB C4B 126.40(16) . . . . ? C14B C3B C3AB C4B -112.33(18) . . . . ? C7AA C3AA C4A N5A -59.2(2) . . . . ? C3A C3AA C4A N5A -174.47(15) . . . . ? C7AB C3AB C4B N5B -61.65(19) . . . . ? C3B C3AB C4B N5B -176.56(15) . . . . ? N5A C6A C7A C27A -153.04(19) . . . . ? N5A C6A C7A C7AA 30.5(2) . . . . ? N5B C6B C7B C27B -151.21(19) . . . . ? N5B C6B C7B C7AB 30.2(2) . . . . ? C27A C7A C7AA N1A -29.1(3) . . . . ? C6A C7A C7AA N1A 147.51(19) . . . . ? C27A C7A C7AA C3AA 156.60(18) . . . . ? C6A C7A C7AA C3AA -26.8(3) . . . . ? C4A C3AA C7AA N1A -133.43(17) . . . . ? C3A C3AA C7AA N1A -7.5(2) . . . . ? C4A C3AA C7AA C7A 41.4(2) . . . . ? C3A C3AA C7AA C7A 167.32(16) . . . . ? C27B C7B C7AB N1B -34.2(3) . . . . ? C6B C7B C7AB N1B 144.46(19) . . . . ? C27B C7B C7AB C3AB 152.26(18) . . . . ? C6B C7B C7AB C3AB -29.1(2) . . . . ? C4B C3AB C7AB N1B -129.28(18) . . . . ? C3B C3AB C7AB N1B -3.7(2) . . . . ? C4B C3AB C7AB C7B 44.9(2) . . . . ? C3B C3AB C7AB C7B 170.46(16) . . . . ? C13A C8A C9A C10A 0.7(3) . . . . ? N2A C8A C9A C10A -176.17(19) . . . . ? C13B C8B C9B C10B 0.4(3) . . . . ? N2B C8B C9B C10B -176.43(18) . . . . ? C8A C9A C10A C11A -0.8(3) . . . . ? C8B C9B C10B C11B -0.5(3) . . . . ? C9A C10A C11A C12A 0.2(3) . . . . ? C9B C10B C11B C12B 0.4(4) . . . . ? C10A C11A C12A C13A 0.6(3) . . . . ? C10B C11B C12B C13B -0.1(4) . . . . ? C11A C12A C13A C8A -0.7(3) . . . . ? C9A C8A C13A C12A 0.0(3) . . . . ? N2A C8A C13A C12A 176.93(19) . . . . ? C11B C12B C13B C8B 0.0(3) . . . . ? C9B C8B C13B C12B -0.1(3) . . . . ? N2B C8B C13B C12B 176.72(18) . . . . ? N2A C3A C14A C19A 7.4(3) . . . . ? C3AA C3A C14A C19A -107.63(19) . . . . ? N2A C3A C14A C15A -174.11(16) . . . . ? C3AA C3A C14A C15A 70.9(2) . . . . ? N2B C3B C14B C19B 2.8(3) . . . . ? C3AB C3B C14B C19B -112.59(19) . . . . ? N2B C3B C14B C15B -178.88(17) . . . . ? C3AB C3B C14B C15B 65.8(2) . . . . ? C19A C14A C15A O1A -178.08(16) . . . . ? C3A C14A C15A O1A 3.4(3) . . . . ? C19A C14A C15A C16A 0.8(3) . . . . ? C3A C14A C15A C16A -177.77(17) . . . . ? C19B C14B C15B O1B -178.16(16) . . . . ? C3B C14B C15B O1B 3.4(2) . . . . ? C19B C14B C15B C16B 0.9(3) . . . . ? C3B C14B C15B C16B -177.53(18) . . . . ? O1A C15A C16A C17A 178.20(19) . . . . ? C14A C15A C16A C17A -0.6(3) . . . . ? O1B C15B C16B C17B 178.14(19) . . . . ? C14B C15B C16B C17B -0.8(3) . . . . ? C15A C16A C17A C18A -0.1(3) . . . . ? C15B C16B C17B C18B 0.0(3) . . . . ? C16A C17A C18A C19A 0.5(3) . . . . ? C16B C17B C18B C19B 0.7(4) . . . . ? C15A C14A C19A C18A -0.4(3) . . . . ? C3A C14A C19A C18A 178.13(18) . . . . ? C17A C18A C19A C14A -0.3(3) . . . . ? C15B C14B C19B C18B -0.2(3) . . . . ? C3B C14B C19B C18B 178.19(19) . . . . ? C17B C18B C19B C14B -0.6(3) . . . . ? N5A C20A C21A C26A -132.3(2) . . . . ? N5A C20A C21A C22A 50.3(3) . . . . ? N5B C20B C21B C22B -119.3(2) . . . . ? N5B C20B C21B C26B 61.6(3) . . . . ? C26A C21A C22A C23A -0.6(3) . . . . ? C20A C21A C22A C23A 176.9(2) . . . . ? C26B C21B C22B C23B 1.0(4) . . . . ? C20B C21B C22B C23B -178.0(2) . . . . ? C21A C22A C23A C24A 0.6(4) . . . . ? C21B C22B C23B C24B 0.0(5) . . . . ? C22A C23A C24A C25A 0.0(4) . . . . ? C22B C23B C24B C25B -1.4(5) . . . . ? C23A C24A C25A C26A -0.6(5) . . . . ? C23B C24B C25B C26B 1.8(5) . . . . ? C22A C21A C26A C25A 0.0(4) . . . . ? C20A C21A C26A C25A -177.6(2) . . . . ? C24A C25A C26A C21A 0.6(5) . . . . ? C24B C25B C26B C21B -0.8(4) . . . . ? C22B C21B C26B C25B -0.7(3) . . . . ? C20B C21B C26B C25B 178.4(2) . . . . ? C7AA C7A C27A C28A 174.7(2) . . . . ? C6A C7A C27A C28A -1.5(3) . . . . ? C7AB C7B C27B C28B 178.61(19) . . . . ? C6B C7B C27B C28B 0.2(3) . . . . ? C7A C27A C28A C33A -31.3(3) . . . . ? C7A C27A C28A C29A 149.8(2) . . . . ? C7B C27B C28B C33B -34.0(3) . . . . ? C7B C27B C28B C29B 146.9(2) . . . . ? C33A C28A C29A O2A -179.13(19) . . . . ? C27A C28A C29A O2A -0.1(3) . . . . ? C33A C28A C29A C30A 1.7(3) . . . . ? C27A C28A C29A C30A -179.3(2) . . . . ? C33B C28B C29B O2B -176.94(17) . . . . ? C27B C28B C29B O2B 2.2(3) . . . . ? C33B C28B C29B C30B 3.4(3) . . . . ? C27B C28B C29B C30B -177.47(18) . . . . ? O2A C29A C30A C31A -179.6(2) . . . . ? C28A C29A C30A C31A -0.5(4) . . . . ? O2B C29B C30B C31B 178.2(2) . . . . ? C28B C29B C30B C31B -2.2(3) . . . . ? C29A C30A C31A C32A -1.2(4) . . . . ? C29B C30B C31B C32B -0.4(4) . . . . ? C30A C31A C32A C33A 1.6(4) . . . . ? C30B C31B C32B C33B 1.7(4) . . . . ? C31A C32A C33A C28A -0.2(4) . . . . ? C29A C28A C33A C32A -1.4(3) . . . . ? C27A C28A C33A C32A 179.7(2) . . . . ? C31B C32B C33B C28B -0.4(3) . . . . ? C29B C28B C33B C32B -2.1(3) . . . . ? C27B C28B C33B C32B 178.8(2) . . . . ? C7A C7AA N1A N2A -177.35(16) . . . . ? C3AA C7AA N1A N2A -2.7(2) . . . . ? C7B C7AB N1B N2B -177.15(17) . . . . ? C3AB C7AB N1B N2B -3.3(2) . . . . ? C7AA N1A N2A C8A 162.07(16) . . . . ? C7AA N1A N2A C3A 12.8(2) . . . . ? C9A C8A N2A N1A -154.74(17) . . . . ? C13A C8A N2A N1A 28.4(2) . . . . ? C9A C8A N2A C3A -9.5(3) . . . . ? C13A C8A N2A C3A 173.70(17) . . . . ? C14A C3A N2A N1A -138.74(15) . . . . ? C3AA C3A N2A N1A -16.62(19) . . . . ? C14A C3A N2A C8A 74.4(2) . . . . ? C3AA C3A N2A C8A -163.48(16) . . . . ? C9B C8B N2B N1B -159.04(17) . . . . ? C13B C8B N2B N1B 24.2(2) . . . . ? C9B C8B N2B C3B -12.9(3) . . . . ? C13B C8B N2B C3B 170.40(16) . . . . ? C7AB N1B N2B C8B 159.31(16) . . . . ? C7AB N1B N2B C3B 9.5(2) . . . . ? C14B C3B N2B C8B 78.9(2) . . . . ? C3AB C3B N2B C8B -159.11(15) . . . . ? C14B C3B N2B N1B -133.30(16) . . . . ? C3AB C3B N2B N1B -11.29(19) . . . . ? C3AA C4A N5A C20A -172.50(16) . . . . ? C3AA C4A N5A C6A 67.3(2) . . . . ? C21A C20A N5A C4A 62.7(2) . . . . ? C21A C20A N5A C6A -174.98(17) . . . . ? C7A C6A N5A C4A -52.6(2) . . . . ? C7A C6A N5A C20A -174.80(16) . . . . ? C3AB C4B N5B C6B 67.81(18) . . . . ? C3AB C4B N5B C20B -171.30(15) . . . . ? C7B C6B N5B C4B -51.5(2) . . . . ? C7B C6B N5B C20B -174.65(17) . . . . ? C21B C20B N5B C4B 62.0(2) . . . . ? C21B C20B N5B C6B -174.75(18) . . . . ? C16A C15A O1A C34A 16.0(3) . . . . ? C14A C15A O1A C34A -165.15(18) . . . . ? C16B C15B O1B C34B 17.1(3) . . . . ? C14B C15B O1B C34B -163.83(18) . . . . ? C30A C29A O2A C35A 2.3(3) . . . . ? C28A C29A O2A C35A -176.9(2) . . . . ? C30B C29B O2B C35B -4.8(3) . . . . ? C28B C29B O2B C35B 175.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.158 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.036 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 C4A H4A2 O1A 0.97 2.41 3.079(2) 126 . C4B H4B2 O1B 0.97 2.40 3.072(2) 126 . C19A H19A N2A 0.93 2.48 2.844(3) 103 . C19B H19B N2B 0.93 2.48 2.842(3) 103 . C12B H12B Cg13 0.93 2.95 3.718(3) 141 2_756 C16B H16B Cg13 0.93 2.93 3.776(3) 152 2_766 C20A H20A Cg11 0.97 2.96 3.923(3) 172 1_555 C25A H25A Cg10 0.93 2.86 3.684(3) 149 2_757 C34B H34F Cg12 0.96 2.99 3.772(3) 140 1_555 data_1c _database_code_depnum_ccdc_archive 'CCDC 887544' #TrackingRef '1c_3_deposit_bks-vit-ums3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 7-(2-fluorobenzylidene)-5-benzyl-3-(2-fluorophenyl)-3,3a,4,5,6,7- hexahydro-2-phenyl-2H-pyrazolo[4,3-c]pyridine ; _chemical_name_common ? _chemical_melting_point 157-159 _chemical_formula_moiety ? _chemical_formula_sum 'C32 H27 F2 N3' _chemical_formula_weight 491.57 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.8417(9) _cell_length_b 14.1308(9) _cell_length_c 16.3607(11) _cell_angle_alpha 81.235(5) _cell_angle_beta 69.026(6) _cell_angle_gamma 69.420(6) _cell_volume 2594.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6319 _cell_measurement_theta_min 2.6624 _cell_measurement_theta_max 29.3581 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_T_min 0.76809 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_detector_area_resol_mean 15.9821 _diffrn_measurement_method '\w scans' _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 20181 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.0745 _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 -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 26.00 _reflns_number_total 10192 _reflns_number_gt 4826 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_structure_solution ? _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^)+(0.0471P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0047(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 10192 _refine_ls_number_parameters 668 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1256 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1529 _refine_ls_wR_factor_gt 0.1160 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.997 _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 C3A C 0.7215(2) 0.76509(17) 0.99483(15) 0.0548(6) Uani 1 1 d . . . H3A H 0.7941 0.7348 0.9472 0.066 Uiso 1 1 calc R . . C3B C 0.69049(19) 0.26310(18) 0.53955(15) 0.0559(6) Uani 1 1 d . . . H3B H 0.7178 0.2342 0.5895 0.067 Uiso 1 1 calc R . . C3AA C 0.64203(19) 0.85897(17) 0.95876(14) 0.0541(6) Uani 1 1 d . . . H3AA H 0.6008 0.9108 1.0033 0.065 Uiso 1 1 calc R . . C3AB C 0.58347(19) 0.35857(18) 0.56795(14) 0.0557(6) Uani 1 1 d . . . H3AB H 0.5848 0.4073 0.5184 0.067 Uiso 1 1 calc R . . C4A C 0.6994(2) 0.90633(18) 0.87222(14) 0.0617(7) Uani 1 1 d . . . H4A1 H 0.7491 0.9400 0.8801 0.074 Uiso 1 1 calc R . . H4A2 H 0.7483 0.8543 0.8295 0.074 Uiso 1 1 calc R . . C4B C 0.5667(2) 0.41155(19) 0.64794(15) 0.0665(7) Uani 1 1 d . . . H4B1 H 0.5712 0.3633 0.6966 0.080 Uiso 1 1 calc R . . H4B2 H 0.6280 0.4420 0.6354 0.080 Uiso 1 1 calc R . . C6A C 0.5339(2) 0.93124(18) 0.82191(15) 0.0633(7) Uani 1 1 d . . . H6A1 H 0.5820 0.8879 0.7724 0.076 Uiso 1 1 calc R . . H6A2 H 0.4713 0.9833 0.8052 0.076 Uiso 1 1 calc R . . C6B C 0.3553(2) 0.4455(2) 0.69900(16) 0.0687(8) Uani 1 1 d . . . H6B1 H 0.2806 0.4998 0.7110 0.082 Uiso 1 1 calc R . . H6B2 H 0.3564 0.4069 0.7532 0.082 Uiso 1 1 calc R . . C7A C 0.4798(2) 0.86925(18) 0.89788(15) 0.0582(7) Uani 1 1 d . . . C7B C 0.3631(2) 0.37772(19) 0.63320(15) 0.0600(7) Uani 1 1 d . . . C7AA C 0.5560(2) 0.81704(18) 0.94914(14) 0.0554(6) Uani 1 1 d . . . C7AB C 0.4838(2) 0.3190(2) 0.58495(15) 0.0556(6) Uani 1 1 d . . . C8A C 0.7037(2) 0.59081(17) 1.02698(13) 0.0534(6) Uani 1 1 d . . . C8B C 0.6928(2) 0.09123(19) 0.51099(16) 0.0618(7) Uani 1 1 d . . . C9A C 0.8068(2) 0.55096(19) 1.04702(14) 0.0653(7) Uani 1 1 d . . . H9A H 0.8432 0.5938 1.0546 0.078 Uiso 1 1 calc R . . C9B C 0.8098(2) 0.0475(2) 0.50323(16) 0.0722(8) Uani 1 1 d . . . H9B H 0.8522 0.0867 0.5081 0.087 Uiso 1 1 calc R . . C10A C 0.8560(2) 0.4472(2) 1.05583(17) 0.0749(8) Uani 1 1 d . . . H10A H 0.9252 0.4209 1.0697 0.090 Uiso 1 1 calc R . . C10B C 0.8646(3) -0.0549(2) 0.4882(2) 0.0908(10) Uani 1 1 d . . . H10B H 0.9432 -0.0841 0.4846 0.109 Uiso 1 1 calc R . . C11A C 0.8042(3) 0.3827(2) 1.04443(17) 0.0814(9) Uani 1 1 d . . . H11A H 0.8378 0.3132 1.0509 0.098 Uiso 1 1 calc R . . C11B C 0.8064(3) -0.1131(2) 0.4787(3) 0.1249(15) Uani 1 1 d . . . H11B H 0.8444 -0.1816 0.4680 0.150 Uiso 1 1 calc R . . C12A C 0.7028(3) 0.4207(2) 1.02357(17) 0.0798(9) Uani 1 1 d . . . H12A H 0.6680 0.3771 1.0151 0.096 Uiso 1 1 calc R . . C12B C 0.6915(3) -0.0703(2) 0.4851(3) 0.1557(19) Uani 1 1 d . . . H12B H 0.6507 -0.1096 0.4779 0.187 Uiso 1 1 calc R . . C13A C 0.6520(2) 0.52470(19) 1.01508(15) 0.0659(7) Uani 1 1 d . . . H13A H 0.5827 0.5503 1.0013 0.079 Uiso 1 1 calc R . . C13B C 0.6349(3) 0.0308(2) 0.5020(3) 0.1164(13) Uani 1 1 d . . . H13B H 0.5555 0.0586 0.5075 0.140 Uiso 1 1 calc R . . C14A C 0.7521(2) 0.78877(17) 1.06836(16) 0.0561(6) Uani 1 1 d . . . C14B C 0.79162(19) 0.27990(18) 0.46344(16) 0.0570(6) Uani 1 1 d . . . C15A C 0.8566(3) 0.8039(2) 1.0542(2) 0.0712(8) Uani 1 1 d . . . C15B C 0.8791(2) 0.3029(2) 0.4773(2) 0.0730(8) Uani 1 1 d . . . C16A C 0.8908(3) 0.8275(2) 1.1165(3) 0.0922(10) Uani 1 1 d . . . H16A H 0.9641 0.8356 1.1028 0.111 Uiso 1 1 calc R . . C16B C 0.9725(3) 0.3199(2) 0.4120(3) 0.0988(11) Uani 1 1 d . . . H16B H 1.0294 0.3359 0.4246 0.119 Uiso 1 1 calc R . . C17A C 0.8125(4) 0.8388(2) 1.1997(3) 0.0941(11) Uani 1 1 d . . . H17A H 0.8321 0.8556 1.2439 0.113 Uiso 1 1 calc R . . C17B C 0.9806(3) 0.3131(2) 0.3281(3) 0.0972(11) Uani 1 1 d . . . H17B H 1.0444 0.3240 0.2826 0.117 Uiso 1 1 calc R . . C18A C 0.7055(3) 0.8257(2) 1.21896(19) 0.0806(9) Uani 1 1 d . . . H18A H 0.6528 0.8340 1.2759 0.097 Uiso 1 1 calc R . . C18B C 0.8960(3) 0.2904(2) 0.3090(2) 0.0946(10) Uani 1 1 d . . . H18B H 0.9023 0.2860 0.2512 0.113 Uiso 1 1 calc R . . C19A C 0.6754(2) 0.80031(18) 1.15410(17) 0.0683(7) Uani 1 1 d . . . H19A H 0.6029 0.7908 1.1680 0.082 Uiso 1 1 calc R . . C19B C 0.8011(2) 0.2743(2) 0.37764(18) 0.0769(8) Uani 1 1 d . . . H19B H 0.7432 0.2595 0.3654 0.092 Uiso 1 1 calc R . . C20A C 0.6606(2) 1.0315(2) 0.75948(15) 0.0713(8) Uani 1 1 d . . . H20A H 0.5995 1.0722 0.7352 0.086 Uiso 1 1 calc R . . H20B H 0.7169 0.9810 0.7172 0.086 Uiso 1 1 calc R . . C20B C 0.4354(2) 0.5512(2) 0.74072(17) 0.0782(8) Uani 1 1 d . . . H20C H 0.4436 0.5074 0.7914 0.094 Uiso 1 1 calc R . . H20D H 0.3560 0.5989 0.7573 0.094 Uiso 1 1 calc R . . C21A C 0.7217(2) 1.0980(2) 0.77257(16) 0.0639(7) Uani 1 1 d . . . C21B C 0.5208(2) 0.6083(2) 0.71676(16) 0.0671(7) Uani 1 1 d . . . C22A C 0.8382(3) 1.0840(3) 0.7267(2) 0.0916(10) Uani 1 1 d . . . H22A H 0.8814 1.0309 0.6884 0.110 Uiso 1 1 calc R . . C22B C 0.5460(3) 0.6594(3) 0.63754(19) 0.0969(10) Uani 1 1 d . . . H22B H 0.5093 0.6583 0.5981 0.116 Uiso 1 1 calc R . . C23A C 0.8922(3) 1.1490(3) 0.7373(3) 0.1124(12) Uani 1 1 d . . . H23A H 0.9715 1.1387 0.7060 0.135 Uiso 1 1 calc R . . C23B C 0.6240(4) 0.7117(3) 0.6158(2) 0.1225(13) Uani 1 1 d . . . H23B H 0.6396 0.7456 0.5617 0.147 Uiso 1 1 calc R . . C24A C 0.8310(4) 1.2274(3) 0.7926(3) 0.1094(12) Uani 1 1 d . . . H24A H 0.8677 1.2702 0.7998 0.131 Uiso 1 1 calc R . . C24B C 0.6792(3) 0.7152(3) 0.6718(3) 0.1087(12) Uani 1 1 d . . . H24B H 0.7334 0.7499 0.6561 0.130 Uiso 1 1 calc R . . C25A C 0.7148(4) 1.2417(3) 0.8371(2) 0.1014(11) Uani 1 1 d . . . H25A H 0.6713 1.2956 0.8745 0.122 Uiso 1 1 calc R . . C25B C 0.6534(3) 0.6668(3) 0.7514(3) 0.0974(11) Uani 1 1 d . . . H25B H 0.6886 0.6698 0.7913 0.117 Uiso 1 1 calc R . . C26A C 0.6612(3) 1.1776(2) 0.82730(19) 0.0834(9) Uani 1 1 d . . . H26A H 0.5818 1.1886 0.8586 0.100 Uiso 1 1 calc R . . C26B C 0.5750(3) 0.6133(2) 0.77306(19) 0.0821(9) Uani 1 1 d . . . H26B H 0.5589 0.5799 0.8274 0.099 Uiso 1 1 calc R . . C27A C 0.3763(2) 0.85600(19) 0.91599(18) 0.0718(8) Uani 1 1 d . . . H27A H 0.3507 0.8231 0.9693 0.086 Uiso 1 1 calc R . . C27B C 0.2719(2) 0.36578(19) 0.62004(16) 0.0651(7) Uani 1 1 d . . . H27B H 0.2908 0.3269 0.5726 0.078 Uiso 1 1 calc R . . C28A C 0.2972(3) 0.88531(19) 0.8648(2) 0.0721(8) Uani 1 1 d . . . C28B C 0.1459(2) 0.40533(18) 0.66986(17) 0.0629(7) Uani 1 1 d . . . C29A C 0.1779(3) 0.9081(2) 0.9044(3) 0.0927(10) Uani 1 1 d . . . C29B C 0.0626(3) 0.4201(2) 0.6311(2) 0.0803(8) Uani 1 1 d . . . C30A C 0.0979(3) 0.9294(3) 0.8612(4) 0.1223(14) Uani 1 1 d . . . H30A H 0.0178 0.9438 0.8916 0.147 Uiso 1 1 calc R . . C30B C -0.0564(3) 0.4512(2) 0.6728(3) 0.0928(10) Uani 1 1 d . . . H30B H -0.1087 0.4612 0.6426 0.111 Uiso 1 1 calc R . . C31A C 0.1403(5) 0.9284(3) 0.7718(4) 0.1329(18) Uani 1 1 d . . . H31A H 0.0888 0.9432 0.7401 0.160 Uiso 1 1 calc R . . C31B C -0.0956(3) 0.4670(2) 0.7608(3) 0.0950(11) Uani 1 1 d . . . H31B H -0.1760 0.4873 0.7914 0.114 Uiso 1 1 calc R . . C32A C 0.2593(4) 0.9056(3) 0.7288(3) 0.1182(13) Uani 1 1 d . . . H32A H 0.2880 0.9041 0.6679 0.142 Uiso 1 1 calc R . . C32B C -0.0180(3) 0.4532(2) 0.8038(2) 0.0890(10) Uani 1 1 d . . . H32B H -0.0454 0.4647 0.8634 0.107 Uiso 1 1 calc R . . C33A C 0.3368(3) 0.8849(2) 0.7749(2) 0.0958(10) Uani 1 1 d . . . H33A H 0.4169 0.8705 0.7446 0.115 Uiso 1 1 calc R . . C33B C 0.1018(2) 0.4222(2) 0.75869(18) 0.0764(8) Uani 1 1 d . . . H33B H 0.1540 0.4124 0.7889 0.092 Uiso 1 1 calc R . . N1A N 0.56255(16) 0.72708(15) 0.98225(12) 0.0599(6) Uani 1 1 d . . . N1B N 0.51480(16) 0.22811(16) 0.55985(12) 0.0609(6) Uani 1 1 d . . . N2A N 0.64980(16) 0.69658(14) 1.02220(12) 0.0566(5) Uani 1 1 d . . . N2B N 0.63781(16) 0.19620(15) 0.51958(13) 0.0594(5) Uani 1 1 d . . . N5A N 0.60704(17) 0.97966(14) 0.84078(12) 0.0582(5) Uani 1 1 d . . . N5B N 0.45095(17) 0.48969(16) 0.67035(12) 0.0630(6) Uani 1 1 d . . . F1A F 0.93421(14) 0.79403(14) 0.96993(13) 0.1090(6) Uani 1 1 d . . . F1B F 0.87203(16) 0.31025(17) 0.56063(13) 0.1251(7) Uani 1 1 d . . . F2A F 0.13548(15) 0.90890(17) 0.99278(16) 0.1342(8) Uani 1 1 d . . . F2B F 0.10214(14) 0.40376(15) 0.54304(12) 0.1122(7) 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 C3A 0.0590(14) 0.0441(13) 0.0584(14) 0.0017(11) -0.0216(12) -0.0120(12) C3B 0.0538(14) 0.0571(16) 0.0607(15) 0.0009(12) -0.0227(12) -0.0196(12) C3AA 0.0629(15) 0.0436(13) 0.0560(14) -0.0002(11) -0.0233(12) -0.0142(12) C3AB 0.0549(14) 0.0604(16) 0.0486(13) -0.0029(12) -0.0168(11) -0.0145(13) C4A 0.0693(16) 0.0572(15) 0.0595(15) 0.0077(12) -0.0252(13) -0.0211(13) C4B 0.0661(16) 0.0707(17) 0.0636(16) -0.0034(14) -0.0216(13) -0.0221(14) C6A 0.0792(17) 0.0512(15) 0.0649(16) 0.0013(13) -0.0331(14) -0.0190(14) C6B 0.0636(16) 0.080(2) 0.0555(15) -0.0015(14) -0.0144(13) -0.0204(15) C7A 0.0666(16) 0.0471(14) 0.0642(16) -0.0014(12) -0.0297(14) -0.0140(13) C7B 0.0545(15) 0.0661(17) 0.0541(14) 0.0058(13) -0.0185(12) -0.0156(13) C7AA 0.0598(15) 0.0477(14) 0.0556(14) 0.0015(12) -0.0195(12) -0.0143(12) C7AB 0.0492(14) 0.0622(17) 0.0546(14) 0.0039(12) -0.0203(12) -0.0159(13) C8A 0.0652(15) 0.0462(14) 0.0403(12) -0.0013(10) -0.0117(11) -0.0138(13) C8B 0.0560(16) 0.0510(15) 0.0775(17) 0.0084(13) -0.0214(13) -0.0210(13) C9A 0.0673(16) 0.0486(15) 0.0670(16) 0.0004(12) -0.0190(13) -0.0073(13) C9B 0.0551(16) 0.0657(19) 0.0935(19) 0.0006(15) -0.0272(14) -0.0152(14) C10A 0.0715(18) 0.0560(17) 0.0760(18) 0.0021(15) -0.0169(14) -0.0046(16) C10B 0.0594(17) 0.068(2) 0.129(3) 0.0058(19) -0.0246(17) -0.0111(17) C11A 0.094(2) 0.0462(17) 0.0789(19) -0.0021(14) -0.0113(17) -0.0101(17) C11B 0.082(2) 0.051(2) 0.230(4) 0.001(2) -0.045(3) -0.0171(19) C12A 0.104(2) 0.0530(17) 0.0770(19) -0.0076(14) -0.0216(17) -0.0244(17) C12B 0.092(3) 0.050(2) 0.334(6) 0.002(3) -0.077(3) -0.0291(19) C13A 0.0822(18) 0.0559(17) 0.0590(15) -0.0018(13) -0.0229(14) -0.0218(15) C13B 0.068(2) 0.0538(19) 0.231(4) 0.006(2) -0.055(2) -0.0223(17) C14A 0.0613(15) 0.0407(13) 0.0713(17) 0.0077(12) -0.0330(14) -0.0147(12) C14B 0.0445(13) 0.0540(15) 0.0678(16) -0.0042(12) -0.0128(12) -0.0151(12) C15A 0.0755(19) 0.0582(17) 0.085(2) 0.0099(15) -0.0336(17) -0.0253(15) C15B 0.0645(17) 0.0728(19) 0.087(2) 0.0046(16) -0.0255(16) -0.0311(15) C16A 0.094(2) 0.080(2) 0.131(3) 0.009(2) -0.066(2) -0.0366(19) C16B 0.079(2) 0.091(2) 0.134(3) 0.017(2) -0.038(2) -0.0429(18) C17A 0.135(3) 0.063(2) 0.123(3) 0.008(2) -0.088(3) -0.035(2) C17B 0.070(2) 0.082(2) 0.119(3) 0.011(2) -0.002(2) -0.0356(18) C18A 0.114(2) 0.0627(18) 0.0748(19) -0.0009(14) -0.0487(18) -0.0216(18) C18B 0.102(2) 0.092(2) 0.0699(19) -0.0013(17) -0.0032(19) -0.035(2) C19A 0.0769(17) 0.0611(17) 0.0676(17) 0.0005(14) -0.0295(15) -0.0181(14) C19B 0.0824(19) 0.089(2) 0.0661(18) -0.0046(15) -0.0162(15) -0.0427(16) C20A 0.0934(19) 0.0669(17) 0.0567(16) 0.0073(13) -0.0287(14) -0.0289(16) C20B 0.0805(19) 0.087(2) 0.0568(16) -0.0111(15) -0.0079(14) -0.0266(17) C21A 0.0777(19) 0.0610(17) 0.0510(15) 0.0142(13) -0.0234(14) -0.0241(15) C21B 0.0791(18) 0.0730(19) 0.0468(15) -0.0153(13) -0.0159(14) -0.0212(15) C22A 0.088(2) 0.091(2) 0.090(2) 0.0038(19) -0.0227(19) -0.030(2) C22B 0.118(3) 0.132(3) 0.0578(19) -0.0029(19) -0.0253(18) -0.065(2) C23A 0.089(3) 0.128(4) 0.122(3) 0.013(3) -0.026(2) -0.054(3) C23B 0.154(3) 0.156(4) 0.074(2) -0.013(2) -0.003(2) -0.102(3) C24A 0.139(4) 0.105(3) 0.128(3) 0.035(3) -0.074(3) -0.075(3) C24B 0.082(2) 0.116(3) 0.118(3) -0.059(3) 0.005(2) -0.035(2) C25A 0.125(3) 0.090(3) 0.104(3) -0.003(2) -0.046(2) -0.043(2) C25B 0.090(2) 0.085(3) 0.127(3) -0.036(2) -0.056(2) -0.005(2) C26A 0.090(2) 0.091(2) 0.080(2) -0.0079(18) -0.0292(17) -0.0386(19) C26B 0.100(2) 0.069(2) 0.0727(19) -0.0129(16) -0.0344(18) -0.0116(18) C27A 0.0751(18) 0.0568(17) 0.0875(19) 0.0070(14) -0.0387(16) -0.0173(15) C27B 0.0555(15) 0.0701(18) 0.0638(15) -0.0045(13) -0.0204(13) -0.0115(14) C28A 0.079(2) 0.0483(16) 0.103(2) 0.0033(15) -0.0500(18) -0.0193(15) C28B 0.0528(15) 0.0549(16) 0.0748(17) 0.0038(13) -0.0200(14) -0.0134(13) C29A 0.089(2) 0.076(2) 0.135(3) 0.015(2) -0.062(2) -0.0346(19) C29B 0.075(2) 0.077(2) 0.089(2) -0.0102(17) -0.0303(18) -0.0176(16) C30A 0.106(3) 0.086(3) 0.215(5) 0.014(3) -0.098(4) -0.039(2) C30B 0.0559(19) 0.084(2) 0.138(3) -0.008(2) -0.0340(19) -0.0173(17) C31A 0.156(4) 0.087(3) 0.221(5) 0.006(3) -0.141(5) -0.039(3) C31B 0.0563(19) 0.076(2) 0.131(3) -0.001(2) -0.008(2) -0.0196(17) C32A 0.167(4) 0.102(3) 0.132(3) -0.012(2) -0.095(3) -0.048(3) C32B 0.0666(19) 0.081(2) 0.091(2) 0.0023(17) -0.0036(17) -0.0149(17) C33A 0.113(2) 0.083(2) 0.115(3) -0.0116(19) -0.067(2) -0.0239(19) C33B 0.0656(18) 0.075(2) 0.0767(19) 0.0076(16) -0.0170(15) -0.0191(15) N1A 0.0636(13) 0.0545(13) 0.0617(12) 0.0029(10) -0.0252(10) -0.0164(11) N1B 0.0501(12) 0.0650(14) 0.0652(13) 0.0019(11) -0.0183(10) -0.0178(11) N2A 0.0630(12) 0.0453(12) 0.0624(12) 0.0033(9) -0.0259(10) -0.0151(10) N2B 0.0457(11) 0.0563(13) 0.0740(13) 0.0004(11) -0.0159(10) -0.0190(10) N5A 0.0740(13) 0.0526(12) 0.0540(11) 0.0086(10) -0.0277(10) -0.0249(11) N5B 0.0627(13) 0.0700(14) 0.0496(12) -0.0108(10) -0.0085(10) -0.0201(12) F1A 0.0840(11) 0.1234(16) 0.1207(14) 0.0040(12) -0.0242(11) -0.0474(11) F1B 0.1251(15) 0.183(2) 0.1147(14) 0.0014(14) -0.0612(12) -0.0852(14) F2A 0.0863(13) 0.166(2) 0.1491(18) 0.0297(17) -0.0391(13) -0.0527(13) F2B 0.0807(11) 0.1490(18) 0.1159(14) -0.0301(12) -0.0465(11) -0.0224(11) _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 C3A N2A 1.478(3) . ? C3A C14A 1.506(3) . ? C3A C3AA 1.546(3) . ? C3A H3A 0.9800 . ? C3B N2B 1.470(3) . ? C3B C14B 1.504(3) . ? C3B C3AB 1.535(3) . ? C3B H3B 0.9800 . ? C3AA C7AA 1.486(3) . ? C3AA C4A 1.519(3) . ? C3AA H3AA 0.9800 . ? C3AB C7AB 1.493(3) . ? C3AB C4B 1.518(3) . ? C3AB H3AB 0.9800 . ? C4A N5A 1.468(2) . ? C4A H4A1 0.9700 . ? C4A H4A2 0.9700 . ? C4B N5B 1.464(3) . ? C4B H4B1 0.9700 . ? C4B H4B2 0.9700 . ? C6A N5A 1.473(3) . ? C6A C7A 1.507(3) . ? C6A H6A1 0.9700 . ? C6A H6A2 0.9700 . ? C6B N5B 1.469(3) . ? C6B C7B 1.502(3) . ? C6B H6B1 0.9700 . ? C6B H6B2 0.9700 . ? C7A C27A 1.329(3) . ? C7A C7AA 1.448(3) . ? C7B C27B 1.333(3) . ? C7B C7AB 1.461(3) . ? C7AA N1A 1.290(3) . ? C7AB N1B 1.288(3) . ? C8A C9A 1.381(3) . ? C8A C13A 1.391(3) . ? C8A N2A 1.412(3) . ? C8B C13B 1.366(4) . ? C8B C9B 1.375(3) . ? C8B N2B 1.405(3) . ? C9A C10A 1.386(3) . ? C9A H9A 0.9300 . ? C9B C10B 1.385(4) . ? C9B H9B 0.9300 . ? C10A C11A 1.369(4) . ? C10A H10A 0.9300 . ? C10B C11B 1.346(4) . ? C10B H10B 0.9300 . ? C11A C12A 1.367(4) . ? C11A H11A 0.9300 . ? C11B C12B 1.354(4) . ? C11B H11B 0.9300 . ? C12A C13A 1.390(3) . ? C12A H12A 0.9300 . ? C12B C13B 1.376(4) . ? C12B H12B 0.9300 . ? C13A H13A 0.9300 . ? C13B H13B 0.9300 . ? C14A C15A 1.366(3) . ? C14A C19A 1.390(3) . ? C14B C15B 1.371(3) . ? C14B C19B 1.377(3) . ? C15A C16A 1.367(4) . ? C15A F1A 1.375(3) . ? C15B F1B 1.351(3) . ? C15B C16B 1.359(4) . ? C16A C17A 1.365(4) . ? C16A H16A 0.9300 . ? C16B C17B 1.355(4) . ? C16B H16B 0.9300 . ? C17A C18A 1.368(4) . ? C17A H17A 0.9300 . ? C17B C18B 1.378(4) . ? C17B H17B 0.9300 . ? C18A C19A 1.383(4) . ? C18A H18A 0.9300 . ? C18B C19B 1.392(4) . ? C18B H18B 0.9300 . ? C19A H19A 0.9300 . ? C19B H19B 0.9300 . ? C20A N5A 1.477(3) . ? C20A C21A 1.499(4) . ? C20A H20A 0.9700 . ? C20A H20B 0.9700 . ? C20B N5B 1.462(3) . ? C20B C21B 1.493(4) . ? C20B H20C 0.9700 . ? C20B H20D 0.9700 . ? C21A C26A 1.366(4) . ? C21A C22A 1.369(4) . ? C21B C26B 1.360(4) . ? C21B C22B 1.373(4) . ? C22A C23A 1.392(5) . ? C22A H22A 0.9300 . ? C22B C23B 1.365(4) . ? C22B H22B 0.9300 . ? C23A C24A 1.358(5) . ? C23A H23A 0.9300 . ? C23B C24B 1.359(4) . ? C23B H23B 0.9300 . ? C24A C25A 1.362(4) . ? C24A H24A 0.9300 . ? C24B C25B 1.361(4) . ? C24B H24B 0.9300 . ? C25A C26A 1.372(4) . ? C25A H25A 0.9300 . ? C25B C26B 1.382(4) . ? C25B H25B 0.9300 . ? C26A H26A 0.9300 . ? C26B H26B 0.9300 . ? C27A C28A 1.453(3) . ? C27A H27A 0.9300 . ? C27B C28B 1.468(3) . ? C27B H27B 0.9300 . ? C28A C29A 1.370(4) . ? C28A C33A 1.375(4) . ? C28B C29B 1.369(3) . ? C28B C33B 1.382(3) . ? C29A F2A 1.351(4) . ? C29A C30A 1.372(4) . ? C29B C30B 1.366(4) . ? C29B F2B 1.372(3) . ? C30A C31A 1.367(5) . ? C30A H30A 0.9300 . ? C30B C31B 1.370(4) . ? C30B H30B 0.9300 . ? C31A C32A 1.373(5) . ? C31A H31A 0.9300 . ? C31B C32B 1.361(4) . ? C31B H31B 0.9300 . ? C32A C33A 1.383(4) . ? C32A H32A 0.9300 . ? C32B C33B 1.384(3) . ? C32B H32B 0.9300 . ? C33A H33A 0.9300 . ? C33B H33B 0.9300 . ? N1A N2A 1.403(2) . ? N1B N2B 1.406(2) . ? 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 N2A C3A C14A 113.21(19) . . ? N2A C3A C3AA 102.22(18) . . ? C14A C3A C3AA 113.10(19) . . ? N2A C3A H3A 109.4 . . ? C14A C3A H3A 109.4 . . ? C3AA C3A H3A 109.4 . . ? N2B C3B C14B 113.1(2) . . ? N2B C3B C3AB 101.44(18) . . ? C14B C3B C3AB 114.4(2) . . ? N2B C3B H3B 109.2 . . ? C14B C3B H3B 109.2 . . ? C3AB C3B H3B 109.2 . . ? C7AA C3AA C4A 109.97(18) . . ? C7AA C3AA C3A 101.12(19) . . ? C4A C3AA C3A 117.67(18) . . ? C7AA C3AA H3AA 109.2 . . ? C4A C3AA H3AA 109.2 . . ? C3A C3AA H3AA 109.2 . . ? C7AB C3AB C4B 110.0(2) . . ? C7AB C3AB C3B 101.7(2) . . ? C4B C3AB C3B 117.97(18) . . ? C7AB C3AB H3AB 108.9 . . ? C4B C3AB H3AB 108.9 . . ? C3B C3AB H3AB 108.9 . . ? N5A C4A C3AA 109.01(18) . . ? N5A C4A H4A1 109.9 . . ? C3AA C4A H4A1 109.9 . . ? N5A C4A H4A2 109.9 . . ? C3AA C4A H4A2 109.9 . . ? H4A1 C4A H4A2 108.3 . . ? N5B C4B C3AB 108.06(18) . . ? N5B C4B H4B1 110.1 . . ? C3AB C4B H4B1 110.1 . . ? N5B C4B H4B2 110.1 . . ? C3AB C4B H4B2 110.1 . . ? H4B1 C4B H4B2 108.4 . . ? N5A C6A C7A 113.75(19) . . ? N5A C6A H6A1 108.8 . . ? C7A C6A H6A1 108.8 . . ? N5A C6A H6A2 108.8 . . ? C7A C6A H6A2 108.8 . . ? H6A1 C6A H6A2 107.7 . . ? N5B C6B C7B 113.7(2) . . ? N5B C6B H6B1 108.8 . . ? C7B C6B H6B1 108.8 . . ? N5B C6B H6B2 108.8 . . ? C7B C6B H6B2 108.8 . . ? H6B1 C6B H6B2 107.7 . . ? C27A C7A C7AA 120.8(2) . . ? C27A C7A C6A 125.7(2) . . ? C7AA C7A C6A 113.3(2) . . ? C27B C7B C7AB 120.8(2) . . ? C27B C7B C6B 125.6(2) . . ? C7AB C7B C6B 113.5(2) . . ? N1A C7AA C7A 122.6(2) . . ? N1A C7AA C3AA 115.13(19) . . ? C7A C7AA C3AA 121.9(2) . . ? N1B C7AB C7B 124.2(3) . . ? N1B C7AB C3AB 114.7(2) . . ? C7B C7AB C3AB 121.0(2) . . ? C9A C8A C13A 118.6(2) . . ? C9A C8A N2A 120.4(2) . . ? C13A C8A N2A 120.9(2) . . ? C13B C8B C9B 117.8(3) . . ? C13B C8B N2B 121.0(2) . . ? C9B C8B N2B 120.9(3) . . ? C8A C9A C10A 120.1(3) . . ? C8A C9A H9A 120.0 . . ? C10A C9A H9A 120.0 . . ? C8B C9B C10B 120.0(3) . . ? C8B C9B H9B 120.0 . . ? C10B C9B H9B 120.0 . . ? C11A C10A C9A 120.9(3) . . ? C11A C10A H10A 119.5 . . ? C9A C10A H10A 119.5 . . ? C11B C10B C9B 121.4(3) . . ? C11B C10B H10B 119.3 . . ? C9B C10B H10B 119.3 . . ? C12A C11A C10A 119.9(3) . . ? C12A C11A H11A 120.1 . . ? C10A C11A H11A 120.1 . . ? C10B C11B C12B 119.0(3) . . ? C10B C11B H11B 120.5 . . ? C12B C11B H11B 120.5 . . ? C11A C12A C13A 119.9(3) . . ? C11A C12A H12A 120.0 . . ? C13A C12A H12A 120.0 . . ? C11B C12B C13B 120.4(3) . . ? C11B C12B H12B 119.8 . . ? C13B C12B H12B 119.8 . . ? C12A C13A C8A 120.6(3) . . ? C12A C13A H13A 119.7 . . ? C8A C13A H13A 119.7 . . ? C8B C13B C12B 121.4(3) . . ? C8B C13B H13B 119.3 . . ? C12B C13B H13B 119.3 . . ? C15A C14A C19A 115.4(3) . . ? C15A C14A C3A 121.7(3) . . ? C19A C14A C3A 122.9(2) . . ? C15B C14B C19B 116.8(2) . . ? C15B C14B C3B 120.5(2) . . ? C19B C14B C3B 122.7(2) . . ? C14A C15A C16A 125.7(3) . . ? C14A C15A F1A 117.0(3) . . ? C16A C15A F1A 117.4(3) . . ? F1B C15B C16B 117.7(3) . . ? F1B C15B C14B 118.5(3) . . ? C16B C15B C14B 123.8(3) . . ? C17A C16A C15A 117.0(3) . . ? C17A C16A H16A 121.5 . . ? C15A C16A H16A 121.5 . . ? C17B C16B C15B 118.3(3) . . ? C17B C16B H16B 120.8 . . ? C15B C16B H16B 120.8 . . ? C16A C17A C18A 120.8(3) . . ? C16A C17A H17A 119.6 . . ? C18A C17A H17A 119.6 . . ? C16B C17B C18B 121.2(3) . . ? C16B C17B H17B 119.4 . . ? C18B C17B H17B 119.4 . . ? C17A C18A C19A 120.2(3) . . ? C17A C18A H18A 119.9 . . ? C19A C18A H18A 119.9 . . ? C17B C18B C19B 118.9(3) . . ? C17B C18B H18B 120.6 . . ? C19B C18B H18B 120.6 . . ? C18A C19A C14A 120.9(3) . . ? C18A C19A H19A 119.5 . . ? C14A C19A H19A 119.5 . . ? C14B C19B C18B 121.0(3) . . ? C14B C19B H19B 119.5 . . ? C18B C19B H19B 119.5 . . ? N5A C20A C21A 113.6(2) . . ? N5A C20A H20A 108.9 . . ? C21A C20A H20A 108.9 . . ? N5A C20A H20B 108.9 . . ? C21A C20A H20B 108.9 . . ? H20A C20A H20B 107.7 . . ? N5B C20B C21B 113.8(2) . . ? N5B C20B H20C 108.8 . . ? C21B C20B H20C 108.8 . . ? N5B C20B H20D 108.8 . . ? C21B C20B H20D 108.8 . . ? H20C C20B H20D 107.7 . . ? C26A C21A C22A 118.1(3) . . ? C26A C21A C20A 120.8(3) . . ? C22A C21A C20A 121.0(3) . . ? C26B C21B C22B 117.6(3) . . ? C26B C21B C20B 121.4(3) . . ? C22B C21B C20B 121.1(3) . . ? C21A C22A C23A 120.1(3) . . ? C21A C22A H22A 120.0 . . ? C23A C22A H22A 120.0 . . ? C23B C22B C21B 121.0(3) . . ? C23B C22B H22B 119.5 . . ? C21B C22B H22B 119.5 . . ? C24A C23A C22A 121.1(4) . . ? C24A C23A H23A 119.4 . . ? C22A C23A H23A 119.4 . . ? C24B C23B C22B 121.2(4) . . ? C24B C23B H23B 119.4 . . ? C22B C23B H23B 119.4 . . ? C23A C24A C25A 118.5(4) . . ? C23A C24A H24A 120.8 . . ? C25A C24A H24A 120.8 . . ? C23B C24B C25B 118.5(4) . . ? C23B C24B H24B 120.7 . . ? C25B C24B H24B 120.7 . . ? C24A C25A C26A 120.7(4) . . ? C24A C25A H25A 119.6 . . ? C26A C25A H25A 119.6 . . ? C24B C25B C26B 120.2(3) . . ? C24B C25B H25B 119.9 . . ? C26B C25B H25B 119.9 . . ? C21A C26A C25A 121.5(3) . . ? C21A C26A H26A 119.3 . . ? C25A C26A H26A 119.3 . . ? C21B C26B C25B 121.5(3) . . ? C21B C26B H26B 119.2 . . ? C25B C26B H26B 119.2 . . ? C7A C27A C28A 129.6(3) . . ? C7A C27A H27A 115.2 . . ? C28A C27A H27A 115.2 . . ? C7B C27B C28B 129.2(2) . . ? C7B C27B H27B 115.4 . . ? C28B C27B H27B 115.4 . . ? C29A C28A C33A 115.8(3) . . ? C29A C28A C27A 121.3(3) . . ? C33A C28A C27A 122.8(3) . . ? C29B C28B C33B 115.1(2) . . ? C29B C28B C27B 120.8(2) . . ? C33B C28B C27B 123.9(2) . . ? F2A C29A C28A 117.7(3) . . ? F2A C29A C30A 117.3(4) . . ? C28A C29A C30A 125.1(4) . . ? C30B C29B C28B 125.3(3) . . ? C30B C29B F2B 117.5(3) . . ? C28B C29B F2B 117.2(2) . . ? C31A C30A C29A 117.6(4) . . ? C31A C30A H30A 121.2 . . ? C29A C30A H30A 121.2 . . ? C29B C30B C31B 117.4(3) . . ? C29B C30B H30B 121.3 . . ? C31B C30B H30B 121.3 . . ? C30A C31A C32A 119.8(4) . . ? C30A C31A H31A 120.1 . . ? C32A C31A H31A 120.1 . . ? C32B C31B C30B 120.6(3) . . ? C32B C31B H31B 119.7 . . ? C30B C31B H31B 119.7 . . ? C31A C32A C33A 120.7(4) . . ? C31A C32A H32A 119.6 . . ? C33A C32A H32A 119.6 . . ? C31B C32B C33B 119.9(3) . . ? C31B C32B H32B 120.0 . . ? C33B C32B H32B 120.0 . . ? C28A C33A C32A 121.0(3) . . ? C28A C33A H33A 119.5 . . ? C32A C33A H33A 119.5 . . ? C28B C33B C32B 121.7(3) . . ? C28B C33B H33B 119.1 . . ? C32B C33B H33B 119.1 . . ? C7AA N1A N2A 107.9(2) . . ? C7AB N1B N2B 107.1(2) . . ? N1A N2A C8A 114.3(2) . . ? N1A N2A C3A 110.46(16) . . ? C8A N2A C3A 120.69(18) . . ? C8B N2B N1B 115.6(2) . . ? C8B N2B C3B 123.29(18) . . ? N1B N2B C3B 111.35(19) . . ? C4A N5A C6A 112.17(19) . . ? C4A N5A C20A 110.04(18) . . ? C6A N5A C20A 107.88(18) . . ? C20B N5B C4B 110.52(19) . . ? C20B N5B C6B 108.35(19) . . ? C4B N5B C6B 111.6(2) . . ? 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 N2A C3A C3AA C7AA -15.0(2) . . . . ? C14A C3A C3AA C7AA -137.1(2) . . . . ? N2A C3A C3AA C4A -134.8(2) . . . . ? C14A C3A C3AA C4A 103.2(3) . . . . ? N2B C3B C3AB C7AB 16.4(2) . . . . ? C14B C3B C3AB C7AB 138.5(2) . . . . ? N2B C3B C3AB C4B 136.8(2) . . . . ? C14B C3B C3AB C4B -101.2(3) . . . . ? C7AA C3AA C4A N5A 53.4(3) . . . . ? C3A C3AA C4A N5A 168.4(2) . . . . ? C7AB C3AB C4B N5B -55.2(3) . . . . ? C3B C3AB C4B N5B -171.2(2) . . . . ? N5A C6A C7A C27A 147.9(3) . . . . ? N5A C6A C7A C7AA -36.2(3) . . . . ? N5B C6B C7B C27B -147.0(2) . . . . ? N5B C6B C7B C7AB 36.0(3) . . . . ? C27A C7A C7AA N1A 34.0(4) . . . . ? C6A C7A C7AA N1A -142.2(2) . . . . ? C27A C7A C7AA C3AA -153.0(2) . . . . ? C6A C7A C7AA C3AA 30.8(3) . . . . ? C4A C3AA C7AA N1A 133.7(2) . . . . ? C3A C3AA C7AA N1A 8.6(3) . . . . ? C4A C3AA C7AA C7A -39.8(3) . . . . ? C3A C3AA C7AA C7A -164.9(2) . . . . ? C27B C7B C7AB N1B -32.3(3) . . . . ? C6B C7B C7AB N1B 144.9(2) . . . . ? C27B C7B C7AB C3AB 153.2(2) . . . . ? C6B C7B C7AB C3AB -29.6(3) . . . . ? C4B C3AB C7AB N1B -135.4(2) . . . . ? C3B C3AB C7AB N1B -9.6(3) . . . . ? C4B C3AB C7AB C7B 39.6(3) . . . . ? C3B C3AB C7AB C7B 165.44(19) . . . . ? C13A C8A C9A C10A -0.7(3) . . . . ? N2A C8A C9A C10A 176.8(2) . . . . ? C13B C8B C9B C10B -1.0(4) . . . . ? N2B C8B C9B C10B -175.1(2) . . . . ? C8A C9A C10A C11A 0.4(4) . . . . ? C8B C9B C10B C11B 1.7(5) . . . . ? C9A C10A C11A C12A 0.4(4) . . . . ? C9B C10B C11B C12B -0.7(6) . . . . ? C10A C11A C12A C13A -0.8(4) . . . . ? C10B C11B C12B C13B -0.8(7) . . . . ? C11A C12A C13A C8A 0.5(4) . . . . ? C9A C8A C13A C12A 0.3(4) . . . . ? N2A C8A C13A C12A -177.2(2) . . . . ? C9B C8B C13B C12B -0.6(5) . . . . ? N2B C8B C13B C12B 173.6(3) . . . . ? C11B C12B C13B C8B 1.5(7) . . . . ? N2A C3A C14A C15A 146.3(2) . . . . ? C3AA C3A C14A C15A -98.0(3) . . . . ? N2A C3A C14A C19A -36.0(3) . . . . ? C3AA C3A C14A C19A 79.7(3) . . . . ? N2B C3B C14B C15B -153.2(2) . . . . ? C3AB C3B C14B C15B 91.4(3) . . . . ? N2B C3B C14B C19B 27.5(3) . . . . ? C3AB C3B C14B C19B -88.0(3) . . . . ? C19A C14A C15A C16A 0.9(4) . . . . ? C3A C14A C15A C16A 178.7(2) . . . . ? C19A C14A C15A F1A -179.4(2) . . . . ? C3A C14A C15A F1A -1.6(3) . . . . ? C19B C14B C15B F1B 179.2(2) . . . . ? C3B C14B C15B F1B -0.2(4) . . . . ? C19B C14B C15B C16B 0.0(4) . . . . ? C3B C14B C15B C16B -179.4(3) . . . . ? C14A C15A C16A C17A -1.3(4) . . . . ? F1A C15A C16A C17A 179.0(2) . . . . ? F1B C15B C16B C17B -179.8(3) . . . . ? C14B C15B C16B C17B -0.6(5) . . . . ? C15A C16A C17A C18A 0.7(5) . . . . ? C15B C16B C17B C18B 0.6(5) . . . . ? C16A C17A C18A C19A 0.3(4) . . . . ? C16B C17B C18B C19B 0.0(5) . . . . ? C17A C18A C19A C14A -0.8(4) . . . . ? C15A C14A C19A C18A 0.2(3) . . . . ? C3A C14A C19A C18A -177.6(2) . . . . ? C15B C14B C19B C18B 0.6(4) . . . . ? C3B C14B C19B C18B 179.9(2) . . . . ? C17B C18B C19B C14B -0.6(5) . . . . ? N5A C20A C21A C26A -60.5(3) . . . . ? N5A C20A C21A C22A 122.9(3) . . . . ? N5B C20B C21B C26B -136.5(2) . . . . ? N5B C20B C21B C22B 44.7(4) . . . . ? C26A C21A C22A C23A 0.8(4) . . . . ? C20A C21A C22A C23A 177.5(3) . . . . ? C26B C21B C22B C23B 1.1(5) . . . . ? C20B C21B C22B C23B 179.9(3) . . . . ? C21A C22A C23A C24A -0.3(5) . . . . ? C21B C22B C23B C24B -0.1(6) . . . . ? C22A C23A C24A C25A -0.6(5) . . . . ? C22B C23B C24B C25B -1.3(6) . . . . ? C23A C24A C25A C26A 0.9(5) . . . . ? C23B C24B C25B C26B 1.7(5) . . . . ? C22A C21A C26A C25A -0.5(4) . . . . ? C20A C21A C26A C25A -177.2(3) . . . . ? C24A C25A C26A C21A -0.4(5) . . . . ? C22B C21B C26B C25B -0.6(4) . . . . ? C20B C21B C26B C25B -179.4(3) . . . . ? C24B C25B C26B C21B -0.8(5) . . . . ? C7AA C7A C27A C28A -167.6(2) . . . . ? C6A C7A C27A C28A 8.1(5) . . . . ? C7AB C7B C27B C28B 170.1(2) . . . . ? C6B C7B C27B C28B -6.8(4) . . . . ? C7A C27A C28A C29A -150.3(3) . . . . ? C7A C27A C28A C33A 34.5(5) . . . . ? C7B C27B C28B C29B 154.6(3) . . . . ? C7B C27B C28B C33B -31.1(4) . . . . ? C33A C28A C29A F2A 179.7(3) . . . . ? C27A C28A C29A F2A 4.3(5) . . . . ? C33A C28A C29A C30A 0.4(5) . . . . ? C27A C28A C29A C30A -175.1(3) . . . . ? C33B C28B C29B C30B 1.4(5) . . . . ? C27B C28B C29B C30B 176.3(3) . . . . ? C33B C28B C29B F2B -179.7(3) . . . . ? C27B C28B C29B F2B -4.8(4) . . . . ? F2A C29A C30A C31A -179.9(4) . . . . ? C28A C29A C30A C31A -0.5(6) . . . . ? C28B C29B C30B C31B -1.4(5) . . . . ? F2B C29B C30B C31B 179.7(3) . . . . ? C29A C30A C31A C32A 0.8(6) . . . . ? C29B C30B C31B C32B 0.9(5) . . . . ? C30A C31A C32A C33A -0.9(6) . . . . ? C30B C31B C32B C33B -0.6(5) . . . . ? C29A C28A C33A C32A -0.5(5) . . . . ? C27A C28A C33A C32A 174.9(3) . . . . ? C31A C32A C33A C28A 0.8(5) . . . . ? C29B C28B C33B C32B -1.0(4) . . . . ? C27B C28B C33B C32B -175.7(3) . . . . ? C31B C32B C33B C28B 0.6(5) . . . . ? C7A C7AA N1A N2A 175.89(19) . . . . ? C3AA C7AA N1A N2A 2.5(3) . . . . ? C7B C7AB N1B N2B -177.27(19) . . . . ? C3AB C7AB N1B N2B -2.5(3) . . . . ? C7AA N1A N2A C8A -153.53(19) . . . . ? C7AA N1A N2A C3A -13.5(2) . . . . ? C9A C8A N2A N1A 166.08(18) . . . . ? C13A C8A N2A N1A -16.5(3) . . . . ? C9A C8A N2A C3A 30.5(3) . . . . ? C13A C8A N2A C3A -152.1(2) . . . . ? C14A C3A N2A N1A 139.99(18) . . . . ? C3AA C3A N2A N1A 18.0(2) . . . . ? C14A C3A N2A C8A -82.9(2) . . . . ? C3AA C3A N2A C8A 155.11(18) . . . . ? C13B C8B N2B N1B 29.7(4) . . . . ? C9B C8B N2B N1B -156.3(2) . . . . ? C13B C8B N2B C3B 172.7(3) . . . . ? C9B C8B N2B C3B -13.4(4) . . . . ? C7AB N1B N2B C8B 161.9(2) . . . . ? C7AB N1B N2B C3B 14.6(2) . . . . ? C14B C3B N2B C8B 73.1(3) . . . . ? C3AB C3B N2B C8B -164.0(2) . . . . ? C14B C3B N2B N1B -142.63(18) . . . . ? C3AB C3B N2B N1B -19.7(2) . . . . ? C3AA C4A N5A C6A -63.4(2) . . . . ? C3AA C4A N5A C20A 176.4(2) . . . . ? C7A C6A N5A C4A 54.8(3) . . . . ? C7A C6A N5A C20A 176.11(18) . . . . ? C21A C20A N5A C4A -66.7(3) . . . . ? C21A C20A N5A C6A 170.6(2) . . . . ? C21B C20B N5B C4B 62.8(3) . . . . ? C21B C20B N5B C6B -174.6(2) . . . . ? C3AB C4B N5B C20B -173.4(2) . . . . ? C3AB C4B N5B C6B 65.9(2) . . . . ? C7B C6B N5B C20B -178.32(19) . . . . ? C7B C6B N5B C4B -56.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.177 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.030 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 C3A H3A F1A 0.98 2.39 2.781(4) 103 . C3B H3B F1B 0.98 2.44 2.781(4) 100 . C13A H13A N1A 0.93 2.40 2.730(3) 100 . C32A H32A Cg10 0.93 2.97 3.761(5) 144 2_666 data_1f _database_code_depnum_ccdc_archive 'CCDC 887545' #TrackingRef '1f_5_deposit bks-vit-ums5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 7-(2,4-dichlorobenzylidene)-5-benzyl-3-(2,4-dichlorophenyl)- 3,3a,4,5,6,7-hexa hydro-2-phenyl-2H-pyrazolo[4,3-c]pyridine ; _chemical_name_common ? _chemical_melting_point 203-205 _chemical_formula_moiety ? _chemical_formula_sum 'C32 H25 Cl4 N3' _chemical_formula_weight 593.35 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' 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/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 13.7524(4) _cell_length_b 15.4132(5) _cell_length_c 13.4826(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.715(3) _cell_angle_gamma 90.00 _cell_volume 2798.36(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 12840 _cell_measurement_theta_min 2.6376 _cell_measurement_theta_max 29.2498 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.408 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 0.451 _exptl_absorpt_correction_T_min 0.76470 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_detector_area_resol_mean 15.9821 _diffrn_measurement_method '\w scans' _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 32638 _diffrn_reflns_av_R_equivalents 0.0496 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5500 _reflns_number_gt 3932 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_structure_solution ? _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^)+(0.0473P)^2^+1.7119P] 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 5500 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0749 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1216 _refine_ls_wR_factor_gt 0.1096 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 C3 C 0.68956(18) 0.52915(15) 0.21300(18) 0.0361(5) Uani 1 1 d . . . H3 H 0.7307 0.5793 0.2390 0.043 Uiso 1 1 calc R . . C3A C 0.60741(17) 0.55693(15) 0.12302(18) 0.0347(5) Uani 1 1 d . . . H3A H 0.5924 0.5086 0.0752 0.042 Uiso 1 1 calc R . . C4 C 0.62611(18) 0.63814(16) 0.06622(19) 0.0403(6) Uani 1 1 d . . . H4A H 0.6513 0.6839 0.1139 0.048 Uiso 1 1 calc R . . H4B H 0.6753 0.6264 0.0256 0.048 Uiso 1 1 calc R . . C6 C 0.45871(18) 0.69173(15) 0.06070(19) 0.0379(6) Uani 1 1 d . . . H6A H 0.3984 0.7106 0.0153 0.045 Uiso 1 1 calc R . . H6B H 0.4845 0.7404 0.1036 0.045 Uiso 1 1 calc R . . C7 C 0.43430(18) 0.61855(15) 0.12583(18) 0.0368(6) Uani 1 1 d . . . C7A C 0.52172(18) 0.57004(15) 0.17501(18) 0.0357(5) Uani 1 1 d . . . C8 C 0.67160(19) 0.48993(16) 0.39149(18) 0.0390(6) Uani 1 1 d . . . C9 C 0.7709(2) 0.50525(18) 0.4309(2) 0.0473(7) Uani 1 1 d . . . H9 H 0.8117 0.5269 0.3896 0.057 Uiso 1 1 calc R . . C10 C 0.8097(2) 0.4882(2) 0.5330(2) 0.0592(8) Uani 1 1 d . . . H10 H 0.8766 0.4982 0.5594 0.071 Uiso 1 1 calc R . . C11 C 0.7499(3) 0.4568(2) 0.5947(2) 0.0627(9) Uani 1 1 d . . . H11 H 0.7762 0.4453 0.6625 0.075 Uiso 1 1 calc R . . C12 C 0.6509(3) 0.44229(19) 0.5558(2) 0.0585(8) Uani 1 1 d . . . H12 H 0.6102 0.4217 0.5979 0.070 Uiso 1 1 calc R . . C13 C 0.6115(2) 0.45805(18) 0.4551(2) 0.0500(7) Uani 1 1 d . . . H13 H 0.5445 0.4474 0.4294 0.060 Uiso 1 1 calc R . . C14 C 0.75498(17) 0.45482(15) 0.19276(17) 0.0339(5) Uani 1 1 d . . . C15 C 0.85723(19) 0.46112(17) 0.2016(2) 0.0412(6) Uani 1 1 d . . . C16 C 0.91607(19) 0.38967(18) 0.1922(2) 0.0454(7) Uani 1 1 d . . . H16 H 0.9845 0.3953 0.1994 0.055 Uiso 1 1 calc R . . C17 C 0.8711(2) 0.31088(17) 0.17208(19) 0.0423(6) Uani 1 1 d . . . C18 C 0.7697(2) 0.30183(17) 0.15697(19) 0.0434(6) Uani 1 1 d . . . H18 H 0.7399 0.2483 0.1395 0.052 Uiso 1 1 calc R . . C19 C 0.71293(18) 0.37374(16) 0.16824(19) 0.0397(6) Uani 1 1 d . . . H19 H 0.6444 0.3676 0.1591 0.048 Uiso 1 1 calc R . . C20 C 0.5498(2) 0.74003(16) -0.0628(2) 0.0444(6) Uani 1 1 d . . . H20A H 0.5785 0.7874 -0.0192 0.053 Uiso 1 1 calc R . . H20B H 0.4866 0.7596 -0.1022 0.053 Uiso 1 1 calc R . . C21 C 0.61783(19) 0.71790(16) -0.1336(2) 0.0401(6) Uani 1 1 d . . . C22 C 0.7095(2) 0.7566(2) -0.1245(2) 0.0569(8) Uani 1 1 d . . . H22 H 0.7295 0.7980 -0.0743 0.068 Uiso 1 1 calc R . . C23 C 0.7721(2) 0.7348(2) -0.1886(3) 0.0696(10) Uani 1 1 d . . . H23 H 0.8339 0.7614 -0.1813 0.083 Uiso 1 1 calc R . . C24 C 0.7435(3) 0.6741(2) -0.2630(3) 0.0680(10) Uani 1 1 d . . . H24 H 0.7858 0.6592 -0.3060 0.082 Uiso 1 1 calc R . . C25 C 0.6525(2) 0.6358(2) -0.2738(2) 0.0610(8) Uani 1 1 d . . . H25 H 0.6326 0.5949 -0.3246 0.073 Uiso 1 1 calc R . . C26 C 0.5898(2) 0.65732(18) -0.2095(2) 0.0490(7) Uani 1 1 d . . . H26 H 0.5280 0.6307 -0.2175 0.059 Uiso 1 1 calc R . . C27 C 0.34454(18) 0.59752(17) 0.14209(19) 0.0410(6) Uani 1 1 d . . . H27 H 0.3414 0.5465 0.1782 0.049 Uiso 1 1 calc R . . C28 C 0.25021(18) 0.64426(17) 0.11048(18) 0.0385(6) Uani 1 1 d . . . C29 C 0.15968(19) 0.60065(18) 0.08683(19) 0.0452(6) Uani 1 1 d . . . C30 C 0.0693(2) 0.6434(2) 0.0675(2) 0.0535(8) Uani 1 1 d . . . H30 H 0.0101 0.6126 0.0518 0.064 Uiso 1 1 calc R . . C31 C 0.0691(2) 0.7325(2) 0.0719(2) 0.0535(8) Uani 1 1 d . . . C32 C 0.1558(2) 0.7785(2) 0.0914(2) 0.0521(7) Uani 1 1 d . . . H32 H 0.1547 0.8388 0.0917 0.062 Uiso 1 1 calc R . . C33 C 0.2450(2) 0.73455(18) 0.1105(2) 0.0455(6) Uani 1 1 d . . . H33 H 0.3037 0.7663 0.1239 0.055 Uiso 1 1 calc R . . N1 N 0.53565(15) 0.54059(13) 0.26562(16) 0.0394(5) Uani 1 1 d . . . N2 N 0.62944(15) 0.50198(14) 0.28790(15) 0.0402(5) Uani 1 1 d . . . N5 N 0.53251(15) 0.66583(12) 0.00044(15) 0.0367(5) Uani 1 1 d . . . Cl1 Cl 0.91745(6) 0.55988(5) 0.22832(7) 0.0723(3) Uani 1 1 d . . . Cl2 Cl 0.94387(6) 0.21902(5) 0.16953(6) 0.0637(2) Uani 1 1 d . . . Cl3 Cl 0.15870(6) 0.48793(5) 0.08167(8) 0.0742(3) Uani 1 1 d . . . Cl4 Cl -0.04389(7) 0.78677(8) 0.05433(7) 0.0883(3) 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 C3 0.0376(13) 0.0353(13) 0.0339(13) -0.0017(10) 0.0043(11) 0.0006(10) C3A 0.0338(13) 0.0359(13) 0.0330(13) -0.0008(10) 0.0031(11) 0.0026(10) C4 0.0357(14) 0.0437(14) 0.0413(14) 0.0055(12) 0.0074(12) 0.0040(11) C6 0.0364(14) 0.0380(13) 0.0376(14) -0.0005(11) 0.0035(11) 0.0025(11) C7 0.0333(13) 0.0410(14) 0.0341(13) -0.0029(11) 0.0024(11) 0.0002(10) C7A 0.0338(13) 0.0376(13) 0.0346(13) 0.0011(11) 0.0040(11) -0.0002(10) C8 0.0468(15) 0.0355(13) 0.0333(13) -0.0008(11) 0.0052(12) 0.0114(11) C9 0.0486(16) 0.0536(17) 0.0385(15) -0.0005(13) 0.0060(13) 0.0080(13) C10 0.0571(19) 0.070(2) 0.0438(17) -0.0079(15) -0.0061(15) 0.0115(16) C11 0.085(3) 0.068(2) 0.0322(15) 0.0044(14) 0.0049(16) 0.0203(18) C12 0.077(2) 0.0594(19) 0.0413(17) 0.0064(14) 0.0182(17) 0.0089(16) C13 0.0543(17) 0.0548(17) 0.0418(16) 0.0038(13) 0.0122(14) 0.0044(13) C14 0.0320(13) 0.0387(13) 0.0301(12) 0.0029(10) 0.0041(10) 0.0018(10) C15 0.0386(14) 0.0462(15) 0.0403(14) 0.0002(12) 0.0111(12) -0.0078(12) C16 0.0318(14) 0.0630(18) 0.0431(15) 0.0020(13) 0.0114(12) 0.0049(12) C17 0.0448(16) 0.0494(15) 0.0331(14) 0.0051(12) 0.0092(12) 0.0133(12) C18 0.0487(16) 0.0400(14) 0.0405(15) -0.0018(11) 0.0070(13) 0.0027(12) C19 0.0334(13) 0.0421(14) 0.0421(15) -0.0017(11) 0.0042(11) 0.0010(11) C20 0.0507(16) 0.0366(14) 0.0454(15) 0.0048(12) 0.0086(13) 0.0015(12) C21 0.0421(15) 0.0350(13) 0.0420(14) 0.0145(11) 0.0057(12) 0.0001(11) C22 0.0524(18) 0.0542(18) 0.0623(19) 0.0095(15) 0.0071(16) -0.0113(14) C23 0.0473(18) 0.075(2) 0.089(3) 0.031(2) 0.0193(19) -0.0056(16) C24 0.067(2) 0.075(2) 0.069(2) 0.0270(19) 0.0321(19) 0.0207(18) C25 0.074(2) 0.0565(18) 0.0543(19) 0.0015(15) 0.0163(17) 0.0084(16) C26 0.0462(16) 0.0480(16) 0.0522(17) 0.0033(14) 0.0084(14) -0.0034(13) C27 0.0378(14) 0.0471(15) 0.0373(14) 0.0051(12) 0.0058(12) 0.0004(11) C28 0.0340(13) 0.0526(16) 0.0291(13) 0.0018(11) 0.0069(11) 0.0014(11) C29 0.0402(15) 0.0588(17) 0.0362(14) 0.0054(13) 0.0064(12) -0.0025(13) C30 0.0326(15) 0.087(2) 0.0408(16) 0.0049(15) 0.0075(12) -0.0037(14) C31 0.0433(17) 0.083(2) 0.0347(15) 0.0042(15) 0.0083(13) 0.0205(15) C32 0.0551(19) 0.0575(17) 0.0447(16) -0.0020(14) 0.0127(14) 0.0147(14) C33 0.0403(15) 0.0546(17) 0.0419(15) -0.0044(13) 0.0092(12) 0.0008(12) N1 0.0345(11) 0.0457(12) 0.0373(12) 0.0029(10) 0.0057(9) 0.0056(9) N2 0.0366(12) 0.0516(13) 0.0326(11) 0.0042(10) 0.0074(9) 0.0098(10) N5 0.0377(11) 0.0353(11) 0.0367(11) 0.0051(9) 0.0069(9) 0.0039(9) Cl1 0.0587(5) 0.0616(5) 0.1030(7) -0.0158(5) 0.0315(5) -0.0262(4) Cl2 0.0685(5) 0.0685(5) 0.0540(4) 0.0034(4) 0.0125(4) 0.0339(4) Cl3 0.0591(5) 0.0593(5) 0.0990(7) 0.0088(5) 0.0039(5) -0.0146(4) Cl4 0.0551(5) 0.1383(9) 0.0705(6) 0.0014(6) 0.0102(4) 0.0446(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 C3 N2 1.489(3) . ? C3 C14 1.515(3) . ? C3 C3A 1.541(3) . ? C3 H3 0.9800 . ? C3A C7A 1.502(3) . ? C3A C4 1.516(3) . ? C3A H3A 0.9800 . ? C4 N5 1.470(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C6 N5 1.478(3) . ? C6 C7 1.509(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C27 1.337(3) . ? C7 C7A 1.456(3) . ? C7A N1 1.281(3) . ? C8 C9 1.381(4) . ? C8 C13 1.396(4) . ? C8 N2 1.412(3) . ? C9 C10 1.397(4) . ? C9 H9 0.9300 . ? C10 C11 1.371(4) . ? C10 H10 0.9300 . ? C11 C12 1.374(4) . ? C11 H11 0.9300 . ? C12 C13 1.378(4) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C19 1.388(3) . ? C14 C15 1.390(3) . ? C15 C16 1.388(4) . ? C15 Cl1 1.735(3) . ? C16 C17 1.365(4) . ? C16 H16 0.9300 . ? C17 C18 1.374(4) . ? C17 Cl2 1.739(3) . ? C18 C19 1.382(3) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 N5 1.475(3) . ? C20 C21 1.505(4) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.377(4) . ? C21 C26 1.381(4) . ? C22 C23 1.380(4) . ? C22 H22 0.9300 . ? C23 C24 1.370(5) . ? C23 H23 0.9300 . ? C24 C25 1.365(5) . ? C24 H24 0.9300 . ? C25 C26 1.381(4) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 C28 1.469(3) . ? C27 H27 0.9300 . ? C28 C33 1.394(4) . ? C28 C29 1.394(4) . ? C29 C30 1.384(4) . ? C29 Cl3 1.739(3) . ? C30 C31 1.373(4) . ? C30 H30 0.9300 . ? C31 C32 1.366(4) . ? C31 Cl4 1.738(3) . ? C32 C33 1.379(4) . ? C32 H32 0.9300 . ? C33 H33 0.9300 . ? N1 N2 1.397(3) . ? 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 N2 C3 C14 109.94(19) . . ? N2 C3 C3A 101.12(18) . . ? C14 C3 C3A 115.8(2) . . ? N2 C3 H3 109.9 . . ? C14 C3 H3 109.9 . . ? C3A C3 H3 109.9 . . ? C7A C3A C4 110.75(19) . . ? C7A C3A C3 100.91(19) . . ? C4 C3A C3 117.0(2) . . ? C7A C3A H3A 109.2 . . ? C4 C3A H3A 109.2 . . ? C3 C3A H3A 109.2 . . ? N5 C4 C3A 109.07(19) . . ? N5 C4 H4A 109.9 . . ? C3A C4 H4A 109.9 . . ? N5 C4 H4B 109.9 . . ? C3A C4 H4B 109.9 . . ? H4A C4 H4B 108.3 . . ? N5 C6 C7 112.14(19) . . ? N5 C6 H6A 109.2 . . ? C7 C6 H6A 109.2 . . ? N5 C6 H6B 109.2 . . ? C7 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C27 C7 C7A 120.4(2) . . ? C27 C7 C6 126.8(2) . . ? C7A C7 C6 112.8(2) . . ? N1 C7A C7 124.5(2) . . ? N1 C7A C3A 114.7(2) . . ? C7 C7A C3A 120.7(2) . . ? C9 C8 C13 119.1(2) . . ? C9 C8 N2 122.2(2) . . ? C13 C8 N2 118.6(2) . . ? C8 C9 C10 119.8(3) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C11 C10 C9 120.6(3) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 119.7(3) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? C11 C12 C13 120.6(3) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C12 C13 C8 120.3(3) . . ? C12 C13 H13 119.9 . . ? C8 C13 H13 119.9 . . ? C19 C14 C15 116.6(2) . . ? C19 C14 C3 119.3(2) . . ? C15 C14 C3 124.0(2) . . ? C16 C15 C14 122.4(2) . . ? C16 C15 Cl1 116.9(2) . . ? C14 C15 Cl1 120.7(2) . . ? C17 C16 C15 118.4(2) . . ? C17 C16 H16 120.8 . . ? C15 C16 H16 120.8 . . ? C16 C17 C18 121.7(2) . . ? C16 C17 Cl2 119.3(2) . . ? C18 C17 Cl2 119.0(2) . . ? C17 C18 C19 118.7(2) . . ? C17 C18 H18 120.6 . . ? C19 C18 H18 120.6 . . ? C18 C19 C14 122.1(2) . . ? C18 C19 H19 119.0 . . ? C14 C19 H19 119.0 . . ? N5 C20 C21 112.7(2) . . ? N5 C20 H20A 109.1 . . ? C21 C20 H20A 109.1 . . ? N5 C20 H20B 109.1 . . ? C21 C20 H20B 109.1 . . ? H20A C20 H20B 107.8 . . ? C22 C21 C26 118.1(3) . . ? C22 C21 C20 121.4(3) . . ? C26 C21 C20 120.5(2) . . ? C21 C22 C23 121.0(3) . . ? C21 C22 H22 119.5 . . ? C23 C22 H22 119.5 . . ? C24 C23 C22 120.1(3) . . ? C24 C23 H23 119.9 . . ? C22 C23 H23 119.9 . . ? C25 C24 C23 119.6(3) . . ? C25 C24 H24 120.2 . . ? C23 C24 H24 120.2 . . ? C24 C25 C26 120.3(3) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C25 C26 C21 120.8(3) . . ? C25 C26 H26 119.6 . . ? C21 C26 H26 119.6 . . ? C7 C27 C28 128.6(2) . . ? C7 C27 H27 115.7 . . ? C28 C27 H27 115.7 . . ? C33 C28 C29 116.0(2) . . ? C33 C28 C27 122.1(2) . . ? C29 C28 C27 121.7(2) . . ? C30 C29 C28 122.6(3) . . ? C30 C29 Cl3 118.0(2) . . ? C28 C29 Cl3 119.4(2) . . ? C31 C30 C29 118.6(3) . . ? C31 C30 H30 120.7 . . ? C29 C30 H30 120.7 . . ? C32 C31 C30 121.1(3) . . ? C32 C31 Cl4 119.8(3) . . ? C30 C31 Cl4 119.0(2) . . ? C31 C32 C33 119.3(3) . . ? C31 C32 H32 120.3 . . ? C33 C32 H32 120.3 . . ? C32 C33 C28 122.3(3) . . ? C32 C33 H33 118.9 . . ? C28 C33 H33 118.9 . . ? C7A N1 N2 107.99(19) . . ? N1 N2 C8 116.40(19) . . ? N1 N2 C3 110.48(18) . . ? C8 N2 C3 122.3(2) . . ? C4 N5 C20 110.48(19) . . ? C4 N5 C6 111.20(19) . . ? C20 N5 C6 108.53(18) . . ? 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 N2 C3 C3A C7A 19.0(2) . . . . ? C14 C3 C3A C7A 137.7(2) . . . . ? N2 C3 C3A C4 139.2(2) . . . . ? C14 C3 C3A C4 -102.1(2) . . . . ? C7A C3A C4 N5 -51.8(3) . . . . ? C3 C3A C4 N5 -166.63(19) . . . . ? N5 C6 C7 C27 -138.9(3) . . . . ? N5 C6 C7 C7A 42.4(3) . . . . ? C27 C7 C7A N1 -37.5(4) . . . . ? C6 C7 C7A N1 141.3(2) . . . . ? C27 C7 C7A C3A 147.3(2) . . . . ? C6 C7 C7A C3A -34.0(3) . . . . ? C4 C3A C7A N1 -136.7(2) . . . . ? C3 C3A C7A N1 -12.1(3) . . . . ? C4 C3A C7A C7 39.0(3) . . . . ? C3 C3A C7A C7 163.6(2) . . . . ? C13 C8 C9 C10 0.5(4) . . . . ? N2 C8 C9 C10 -176.8(2) . . . . ? C8 C9 C10 C11 -0.4(4) . . . . ? C9 C10 C11 C12 -0.2(5) . . . . ? C10 C11 C12 C13 0.8(5) . . . . ? C11 C12 C13 C8 -0.7(4) . . . . ? C9 C8 C13 C12 0.1(4) . . . . ? N2 C8 C13 C12 177.5(2) . . . . ? N2 C3 C14 C19 50.6(3) . . . . ? C3A C3 C14 C19 -63.2(3) . . . . ? N2 C3 C14 C15 -126.3(2) . . . . ? C3A C3 C14 C15 119.9(3) . . . . ? C19 C14 C15 C16 -3.5(4) . . . . ? C3 C14 C15 C16 173.5(2) . . . . ? C19 C14 C15 Cl1 178.10(19) . . . . ? C3 C14 C15 Cl1 -4.9(3) . . . . ? C14 C15 C16 C17 1.0(4) . . . . ? Cl1 C15 C16 C17 179.4(2) . . . . ? C15 C16 C17 C18 2.8(4) . . . . ? C15 C16 C17 Cl2 -175.11(19) . . . . ? C16 C17 C18 C19 -3.7(4) . . . . ? Cl2 C17 C18 C19 174.15(19) . . . . ? C17 C18 C19 C14 1.0(4) . . . . ? C15 C14 C19 C18 2.5(4) . . . . ? C3 C14 C19 C18 -174.7(2) . . . . ? N5 C20 C21 C22 -115.2(3) . . . . ? N5 C20 C21 C26 64.3(3) . . . . ? C26 C21 C22 C23 -0.6(4) . . . . ? C20 C21 C22 C23 178.9(3) . . . . ? C21 C22 C23 C24 0.2(5) . . . . ? C22 C23 C24 C25 0.4(5) . . . . ? C23 C24 C25 C26 -0.5(5) . . . . ? C24 C25 C26 C21 0.1(4) . . . . ? C22 C21 C26 C25 0.5(4) . . . . ? C20 C21 C26 C25 -179.0(2) . . . . ? C7A C7 C27 C28 171.6(2) . . . . ? C6 C7 C27 C28 -7.0(4) . . . . ? C7 C27 C28 C33 -37.5(4) . . . . ? C7 C27 C28 C29 147.9(3) . . . . ? C33 C28 C29 C30 -2.0(4) . . . . ? C27 C28 C29 C30 172.9(2) . . . . ? C33 C28 C29 Cl3 178.36(19) . . . . ? C27 C28 C29 Cl3 -6.8(3) . . . . ? C28 C29 C30 C31 -0.1(4) . . . . ? Cl3 C29 C30 C31 179.6(2) . . . . ? C29 C30 C31 C32 2.3(4) . . . . ? C29 C30 C31 Cl4 -176.6(2) . . . . ? C30 C31 C32 C33 -2.4(4) . . . . ? Cl4 C31 C32 C33 176.5(2) . . . . ? C31 C32 C33 C28 0.2(4) . . . . ? C29 C28 C33 C32 1.9(4) . . . . ? C27 C28 C33 C32 -172.9(2) . . . . ? C7 C7A N1 N2 -176.9(2) . . . . ? C3A C7A N1 N2 -1.4(3) . . . . ? C7A N1 N2 C8 160.9(2) . . . . ? C7A N1 N2 C3 15.5(3) . . . . ? C9 C8 N2 N1 -138.8(2) . . . . ? C13 C8 N2 N1 43.9(3) . . . . ? C9 C8 N2 C3 2.1(4) . . . . ? C13 C8 N2 C3 -175.2(2) . . . . ? C14 C3 N2 N1 -144.9(2) . . . . ? C3A C3 N2 N1 -22.0(2) . . . . ? C14 C3 N2 C8 72.2(3) . . . . ? C3A C3 N2 C8 -164.9(2) . . . . ? C3A C4 N5 C20 -174.87(19) . . . . ? C3A C4 N5 C6 64.6(2) . . . . ? C21 C20 N5 C4 62.5(3) . . . . ? C21 C20 N5 C6 -175.3(2) . . . . ? C7 C6 N5 C4 -59.9(3) . . . . ? C7 C6 N5 C20 178.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.371 _refine_diff_density_min -0.406 _refine_diff_density_rms 0.046 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 C3 H3 Cl1 0.98 2.62 3.135(3) 113 . C27 H27 Cl3 0.93 2.74 3.034(3) 100 . #C29 Cl3 Cg5 [ 3665.01] 3.7407(15) 137.87(10) 5.164(3) #[ 3665] = 1-X,1-Y,-Z