# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_if2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H34' _chemical_formula_weight 538.69 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' _symmetry_cell_setting monoclini _symmetry_space_group_name_H-M 'C 2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.515(2) _cell_length_b 15.214(2) _cell_length_c 13.3114(17) _cell_angle_alpha 90.00 _cell_angle_beta 99.134(3) _cell_angle_gamma 90.00 _cell_volume 2902.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Plate _exptl_crystal_colour Blue _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.233 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9338 _exptl_absorpt_correction_T_max 0.9862 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13615 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 27.42 _reflns_number_total 3282 _reflns_number_gt 2570 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)' _computing_publication_material 'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)' _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^)+(0.0622P)^2^+2.9072P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3282 _refine_ls_number_parameters 258 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0617 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1460 _refine_ls_wR_factor_gt 0.1147 _refine_ls_goodness_of_fit_ref 1.145 _refine_ls_restrained_S_all 1.145 _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 C1 C 0.07073(11) 0.17561(10) 0.16096(12) 0.0210(3) Uani 1 1 d . A 1 C2 C 0.08771(11) 0.26977(10) 0.18987(12) 0.0220(3) Uani 1 1 d . A 1 C3 C 0.05044(11) 0.02365(10) 0.16656(12) 0.0216(3) Uani 1 1 d . A 1 C4 C 0.12898(12) 0.44726(11) 0.24221(14) 0.0288(4) Uani 1 1 d . A 1 C5 C 0.15034(11) 0.29036(10) 0.27840(13) 0.0245(3) Uani 1 1 d . A 1 C6 C 0.17007(12) 0.37865(11) 0.30368(14) 0.0282(4) Uani 1 1 d . A 1 H1 H 0.2132(15) 0.3929(13) 0.3692(16) 0.033(5) Uiso 1 1 d . B 1 C7 C 0.10300(11) 0.04206(10) 0.08275(12) 0.0224(3) Uani 1 1 d . A 1 C8 C 0.02776(10) 0.10846(10) 0.20910(12) 0.0208(3) Uani 1 1 d . . 1 C9 C 0.11522(11) 0.13473(10) 0.08060(12) 0.0230(3) Uani 1 1 d . A 1 C10 C 0.04830(12) 0.33837(10) 0.12510(13) 0.0254(4) Uani 1 1 d . A 1 C11 C 0.16307(12) 0.17424(11) 0.00985(13) 0.0263(4) Uani 1 1 d . A 1 H2 H 0.1700(14) 0.2394(14) 0.0096(15) 0.032(5) Uiso 1 1 d . C 1 C12 C 0.02790(11) -0.05617(10) 0.20874(12) 0.0240(4) Uani 1 1 d . . 1 C13 C 0.06976(12) 0.42574(11) 0.15329(14) 0.0275(4) Uani 1 1 d . A 1 H3 H 0.0387(15) 0.4739(14) 0.1069(16) 0.034(5) Uiso 1 1 d . D 1 C14 C 0.05931(13) -0.13984(11) 0.17629(13) 0.0300(4) Uani 1 1 d . E 1 H4 H 0.1039(15) -0.1399(13) 0.1250(15) 0.033(5) Uiso 1 1 d . F 1 C15 C 0.13718(12) -0.00974(11) 0.01006(13) 0.0262(4) Uani 1 1 d . A 1 H5 H 0.1260(13) -0.0748(13) 0.0049(14) 0.025(5) Uiso 1 1 d . G 1 C16 C 0.19873(14) 0.21876(12) 0.34699(15) 0.0336(4) Uani 1 1 d . A 1 H6 H 0.1549(19) 0.1848(17) 0.3814(19) 0.057(7) Uiso 1 1 d . H 1 H7 H 0.2452(18) 0.2464(17) 0.4053(19) 0.054(7) Uiso 1 1 d . I 1 H8 H 0.231(2) 0.1782(19) 0.308(2) 0.069(8) Uiso 1 1 d . J 1 C17 C 0.03181(15) -0.21694(11) 0.21453(14) 0.0349(4) Uani 1 1 d . . 1 H9 H 0.0547(16) -0.2747(16) 0.1910(17) 0.047(6) Uiso 1 1 d . K 1 C18 C 0.18591(12) 0.03029(12) -0.06056(13) 0.0292(4) Uani 1 1 d . A 1 H10 H 0.2090(15) -0.0067(14) -0.1129(16) 0.038(6) Uiso 1 1 d . L 1 C19 C -0.01590(14) 0.32066(13) 0.02706(14) 0.0329(4) Uani 1 1 d . A 1 H11 H -0.073(2) 0.3602(18) 0.0188(19) 0.061(7) Uiso 1 1 d . M 1 H12 H -0.039(2) 0.261(2) 0.021(2) 0.071(8) Uiso 1 1 d . N 1 H13 H 0.017(2) 0.3306(19) -0.034(2) 0.077(9) Uiso 1 1 d . O 1 C20 C 0.19915(12) 0.12087(12) -0.06109(13) 0.0290(4) Uani 1 1 d . A 1 H14 H 0.2315(16) 0.1480(14) -0.1119(17) 0.041(6) Uiso 1 1 d . P 1 C21 C 0.14652(16) 0.54222(12) 0.2741(2) 0.0419(5) Uani 1 1 d . A 1 H15 H 0.137(2) 0.583(2) 0.214(2) 0.075(9) Uiso 1 1 d . Q 1 H16 H 0.212(2) 0.553(2) 0.311(2) 0.085(10) Uiso 1 1 d . R 1 H17 H 0.103(3) 0.562(2) 0.318(3) 0.092(11) Uiso 1 1 d . S 1 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 C1 0.0199(7) 0.0203(8) 0.0235(8) -0.0007(6) 0.0061(6) -0.0002(6) C2 0.0224(8) 0.0175(7) 0.0292(8) -0.0004(6) 0.0133(6) -0.0011(6) C3 0.0212(7) 0.0183(7) 0.0257(8) -0.0021(6) 0.0047(6) 0.0017(6) C4 0.0264(8) 0.0185(8) 0.0444(10) -0.0022(7) 0.0142(7) -0.0024(6) C5 0.0233(8) 0.0203(8) 0.0319(9) -0.0002(6) 0.0108(6) 0.0001(6) C6 0.0241(8) 0.0241(8) 0.0374(10) -0.0059(7) 0.0082(7) -0.0031(6) C7 0.0188(7) 0.0222(8) 0.0265(8) -0.0018(6) 0.0048(6) 0.0012(6) C8 0.0202(7) 0.0169(7) 0.0259(8) -0.0017(6) 0.0055(6) 0.0005(5) C9 0.0209(8) 0.0227(8) 0.0264(8) -0.0021(6) 0.0066(6) 0.0005(6) C10 0.0269(8) 0.0214(8) 0.0310(9) 0.0017(6) 0.0141(6) 0.0004(6) C11 0.0250(8) 0.0253(8) 0.0305(9) -0.0010(6) 0.0103(6) -0.0009(6) C12 0.0278(8) 0.0176(7) 0.0265(8) -0.0009(6) 0.0045(6) 0.0014(6) C13 0.0289(9) 0.0190(8) 0.0370(9) 0.0039(7) 0.0127(7) 0.0011(6) C14 0.0383(10) 0.0212(8) 0.0309(9) -0.0026(7) 0.0066(7) 0.0039(7) C15 0.0264(8) 0.0238(8) 0.0292(9) -0.0041(6) 0.0067(6) 0.0022(6) C16 0.0362(10) 0.0252(9) 0.0382(10) -0.0007(7) 0.0025(8) 0.0023(7) C17 0.0528(12) 0.0189(8) 0.0324(10) -0.0023(7) 0.0050(8) 0.0044(8) C18 0.0278(9) 0.0329(9) 0.0284(9) -0.0074(7) 0.0093(7) 0.0021(7) C19 0.0396(10) 0.0281(9) 0.0313(10) 0.0021(7) 0.0064(7) 0.0034(8) C20 0.0276(9) 0.0339(9) 0.0277(9) -0.0027(7) 0.0110(7) -0.0012(7) C21 0.0406(11) 0.0201(9) 0.0658(15) -0.0063(9) 0.0109(10) -0.0047(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 C1 C8 1.404(2) . ? C1 C9 1.472(2) . ? C1 C2 1.494(2) . ? C2 C5 1.405(2) . ? C2 C10 1.415(2) . ? C3 C12 1.398(2) . ? C3 C8 1.467(2) . ? C3 C7 1.475(2) . ? C4 C13 1.387(3) . ? C4 C6 1.400(3) . ? C4 C21 1.516(2) . ? C5 C6 1.403(2) . ? C5 C16 1.520(2) . ? C6 H1 1.01(2) . ? C7 C15 1.399(2) . ? C7 C9 1.422(2) . ? C8 C8 1.454(3) 2 ? C9 C11 1.392(2) . ? C10 C13 1.403(2) . ? C10 C19 1.503(3) . ? C11 C20 1.408(2) . ? C11 H2 1.00(2) . ? C12 C14 1.441(2) . ? C12 C12 1.465(3) 2 ? C13 H3 1.02(2) . ? C14 C17 1.363(3) . ? C14 H4 1.01(2) . ? C15 C18 1.402(2) . ? C15 H5 1.004(19) . ? C16 H6 0.99(3) . ? C16 H7 1.03(3) . ? C16 H8 0.98(3) . ? C17 C17 1.422(4) 2 ? C17 H9 1.01(2) . ? C18 C20 1.392(3) . ? C18 H10 0.99(2) . ? C19 H11 1.02(3) . ? C19 H12 0.97(3) . ? C19 H13 1.02(3) . ? C20 H14 0.97(2) . ? C21 H15 1.00(3) . ? C21 H16 1.01(3) . ? C21 H17 0.98(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 C1 C9 107.59(13) . . ? C8 C1 C2 130.36(14) . . ? C9 C1 C2 121.26(13) . . ? C5 C2 C10 119.46(14) . . ? C5 C2 C1 119.23(14) . . ? C10 C2 C1 121.07(14) . . ? C12 C3 C8 121.84(14) . . ? C12 C3 C7 130.60(14) . . ? C8 C3 C7 107.43(13) . . ? C13 C4 C6 118.13(15) . . ? C13 C4 C21 121.18(17) . . ? C6 C4 C21 120.65(18) . . ? C6 C5 C2 119.66(15) . . ? C6 C5 C16 119.00(16) . . ? C2 C5 C16 121.33(14) . . ? C4 C6 C5 121.46(16) . . ? C4 C6 H1 119.4(12) . . ? C5 C6 H1 119.1(12) . . ? C15 C7 C9 119.06(15) . . ? C15 C7 C3 134.36(15) . . ? C9 C7 C3 106.54(13) . . ? C1 C8 C8 132.94(9) . 2 ? C1 C8 C3 108.70(13) . . ? C8 C8 C3 118.29(8) 2 . ? C11 C9 C7 121.26(14) . . ? C11 C9 C1 129.25(15) . . ? C7 C9 C1 109.49(13) . . ? C13 C10 C2 118.99(16) . . ? C13 C10 C19 118.88(15) . . ? C2 C10 C19 122.13(15) . . ? C9 C11 C20 118.91(16) . . ? C9 C11 H2 119.6(12) . . ? C20 C11 H2 121.5(12) . . ? C3 C12 C14 122.77(15) . . ? C3 C12 C12 119.58(9) . 2 ? C14 C12 C12 117.63(10) . 2 ? C4 C13 C10 122.22(16) . . ? C4 C13 H3 120.3(12) . . ? C10 C13 H3 117.5(12) . . ? C17 C14 C12 121.51(17) . . ? C17 C14 H4 120.5(12) . . ? C12 C14 H4 118.0(12) . . ? C7 C15 C18 119.42(16) . . ? C7 C15 H5 122.1(11) . . ? C18 C15 H5 118.4(11) . . ? C5 C16 H6 112.5(15) . . ? C5 C16 H7 110.1(14) . . ? H6 C16 H7 105(2) . . ? C5 C16 H8 110.3(17) . . ? H6 C16 H8 109(2) . . ? H7 C16 H8 110(2) . . ? C14 C17 C17 120.50(11) . 2 ? C14 C17 H9 120.3(13) . . ? C17 C17 H9 119.2(13) 2 . ? C20 C18 C15 121.22(15) . . ? C20 C18 H10 119.6(12) . . ? C15 C18 H10 119.1(13) . . ? C10 C19 H11 111.8(14) . . ? C10 C19 H12 113.2(17) . . ? H11 C19 H12 107(2) . . ? C10 C19 H13 111.0(17) . . ? H11 C19 H13 108(2) . . ? H12 C19 H13 106(2) . . ? C18 C20 C11 120.09(16) . . ? C18 C20 H14 120.4(13) . . ? C11 C20 H14 119.5(13) . . ? C4 C21 H15 111.3(17) . . ? C4 C21 H16 113.4(18) . . ? H15 C21 H16 106(2) . . ? C4 C21 H17 112(2) . . ? H15 C21 H17 105(3) . . ? H16 C21 H17 108(3) . . ? 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 C8 C1 C2 C5 66.8(2) . . . . ? C9 C1 C2 C5 -101.62(18) . . . . ? C8 C1 C2 C10 -118.83(19) . . . . ? C9 C1 C2 C10 72.7(2) . . . . ? C10 C2 C5 C6 2.6(2) . . . . ? C1 C2 C5 C6 177.04(14) . . . . ? C10 C2 C5 C16 -176.39(15) . . . . ? C1 C2 C5 C16 -2.0(2) . . . . ? C13 C4 C6 C5 -1.8(2) . . . . ? C21 C4 C6 C5 176.20(17) . . . . ? C2 C5 C6 C4 -0.3(2) . . . . ? C16 C5 C6 C4 178.71(16) . . . . ? C12 C3 C7 C15 9.6(3) . . . . ? C8 C3 C7 C15 -174.56(17) . . . . ? C12 C3 C7 C9 -172.62(16) . . . . ? C8 C3 C7 C9 3.24(17) . . . . ? C9 C1 C8 C8 -178.3(2) . . . 2 ? C2 C1 C8 C8 12.0(3) . . . 2 ? C9 C1 C8 C3 4.65(17) . . . . ? C2 C1 C8 C3 -165.01(15) . . . . ? C12 C3 C8 C1 171.33(15) . . . . ? C7 C3 C8 C1 -4.96(17) . . . . ? C12 C3 C8 C8 -6.2(3) . . . 2 ? C7 C3 C8 C8 177.53(17) . . . 2 ? C15 C7 C9 C11 -2.2(2) . . . . ? C3 C7 C9 C11 179.65(15) . . . . ? C15 C7 C9 C1 177.75(14) . . . . ? C3 C7 C9 C1 -0.45(17) . . . . ? C8 C1 C9 C11 177.26(17) . . . . ? C2 C1 C9 C11 -11.9(3) . . . . ? C8 C1 C9 C7 -2.64(18) . . . . ? C2 C1 C9 C7 168.16(14) . . . . ? C5 C2 C10 C13 -2.7(2) . . . . ? C1 C2 C10 C13 -177.04(14) . . . . ? C5 C2 C10 C19 177.34(15) . . . . ? C1 C2 C10 C19 3.0(2) . . . . ? C7 C9 C11 C20 0.5(2) . . . . ? C1 C9 C11 C20 -179.38(16) . . . . ? C8 C3 C12 C14 -172.22(15) . . . . ? C7 C3 C12 C14 3.1(3) . . . . ? C8 C3 C12 C12 6.1(3) . . . 2 ? C7 C3 C12 C12 -178.51(17) . . . 2 ? C6 C4 C13 C10 1.7(2) . . . . ? C21 C4 C13 C10 -176.30(17) . . . . ? C2 C10 C13 C4 0.5(2) . . . . ? C19 C10 C13 C4 -179.51(16) . . . . ? C3 C12 C14 C17 -176.11(17) . . . . ? C12 C12 C14 C17 5.5(3) 2 . . . ? C9 C7 C15 C18 2.6(2) . . . . ? C3 C7 C15 C18 -179.84(17) . . . . ? C12 C14 C17 C17 2.3(3) . . . 2 ? C7 C15 C18 C20 -1.4(3) . . . . ? C15 C18 C20 C11 -0.2(3) . . . . ? C9 C11 C20 C18 0.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.42 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.338 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.058 _database_code_depnum_ccdc_archive 'CCDC 960644' ####################################################################### # # 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_ddq1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50 H34 Cl2 N2 O2' _chemical_formula_weight 765.69 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.251(3) _cell_length_b 18.592(6) _cell_length_c 22.277(7) _cell_angle_alpha 90.00 _cell_angle_beta 94.409(9) _cell_angle_gamma 90.00 _cell_volume 3820(2) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Plate _exptl_crystal_colour Purple _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1592 _exptl_absorpt_coefficient_mu 0.215 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9000 _exptl_absorpt_correction_T_max 0.9788 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37126 _diffrn_reflns_av_R_equivalents 0.1799 _diffrn_reflns_av_sigmaI/netI 0.1427 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 27.39 _reflns_number_total 8615 _reflns_number_gt 4466 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)' _computing_publication_material 'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)' _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^)+(0.1364P)^2^+0.8725P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0015(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8615 _refine_ls_number_parameters 642 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1697 _refine_ls_R_factor_gt 0.0946 _refine_ls_wR_factor_ref 0.2868 _refine_ls_wR_factor_gt 0.2204 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.14027(14) 0.42786(8) 0.14097(7) 0.0520(4) Uani 1 1 d . . . Cl2 Cl 0.39666(17) 0.54400(7) 0.15353(7) 0.0592(5) Uani 1 1 d . . . O1 O 0.2705(4) 0.28737(18) 0.17313(15) 0.0381(8) Uani 1 1 d . . . O2 O 0.6650(4) 0.47127(18) 0.20086(15) 0.0420(8) Uani 1 1 d . . . C2 C 0.4477(5) 0.2394(2) 0.3909(2) 0.0274(9) Uani 1 1 d . . . N1 N 0.5565(4) 0.1982(2) 0.23199(19) 0.0378(9) Uani 1 1 d . . . C48 C 0.7082(5) 0.3550(2) 0.2695(2) 0.0294(9) Uani 1 1 d . . . N2 N 0.8233(4) 0.3320(2) 0.27263(19) 0.0377(9) Uani 1 1 d . . . C3 C 0.8644(5) 0.3249(2) 0.4839(2) 0.0304(10) Uani 1 1 d . . . C4 C 0.6683(4) 0.3877(2) 0.41885(19) 0.0253(9) Uani 1 1 d . . . C29 C 0.5378(4) 0.4255(2) 0.32794(19) 0.0244(9) Uani 1 1 d . . . C42 C 0.4422(4) 0.3238(2) 0.25420(19) 0.0257(9) Uani 1 1 d . . . C30 C 0.6496(4) 0.4818(2) 0.3470(2) 0.0269(9) Uani 1 1 d . . . C31 C 0.7223(5) 0.4591(2) 0.4015(2) 0.0276(9) Uani 1 1 d . . . C22 C 0.3510(4) 0.3185(2) 0.31349(19) 0.0247(9) Uani 1 1 d . . . C49 C 0.5096(5) 0.2530(2) 0.2428(2) 0.0301(10) Uani 1 1 d . . . C32 C 0.8241(5) 0.5035(2) 0.4327(2) 0.0326(10) Uani 1 1 d . . . H1 H 0.867(6) 0.486(3) 0.474(3) 0.054(16) Uiso 1 1 d . . . C23 C 0.4659(4) 0.3063(2) 0.36650(19) 0.0249(9) Uani 1 1 d . . . C36 C 0.3299(5) 0.5187(2) 0.3305(2) 0.0314(10) Uani 1 1 d . . . H2 H 0.391(6) 0.557(3) 0.341(2) 0.050(16) Uiso 1 1 d . . . C43 C 0.3330(5) 0.3371(2) 0.1990(2) 0.0303(10) Uani 1 1 d . . . C24 C 0.2582(5) 0.2513(2) 0.3139(2) 0.0271(9) Uani 1 1 d . . . C37 C 0.2811(5) 0.3914(2) 0.31835(19) 0.0267(9) Uani 1 1 d . . . C5 C 0.6788(5) 0.1781(2) 0.4296(2) 0.0307(10) Uani 1 1 d . . . C1 C 0.5625(4) 0.3669(2) 0.37622(19) 0.0245(9) Uani 1 1 d . . . C25 C 0.3210(5) 0.2050(2) 0.3582(2) 0.0297(10) Uani 1 1 d . . . C26 C 0.2642(5) 0.1365(2) 0.3663(2) 0.0346(10) Uani 1 1 d . . . H3 H 0.306(5) 0.103(2) 0.399(2) 0.030(12) Uiso 1 1 d . . . C6 C 0.5339(5) 0.1991(2) 0.4388(2) 0.0295(10) Uani 1 1 d . . . C33 C 0.7823(5) 0.5930(2) 0.3546(2) 0.0339(10) Uani 1 1 d . . . H4 H 0.804(4) 0.642(2) 0.3379(18) 0.017(10) Uiso 1 1 d . . . C7 C 0.0745(5) 0.1636(3) 0.2884(2) 0.0361(11) Uani 1 1 d . . . H5 H -0.012(6) 0.149(3) 0.265(3) 0.050(16) Uiso 1 1 d . . . C8 C 0.7533(5) 0.2025(3) 0.3752(2) 0.0364(11) Uani 1 1 d . . . H6 H 0.864(7) 0.189(3) 0.380(3) 0.063(18) Uiso 1 1 d . . . H7 H 0.758(5) 0.261(3) 0.371(2) 0.040(14) Uiso 1 1 d . . . H8 H 0.700(6) 0.187(3) 0.336(3) 0.054(16) Uiso 1 1 d . . . C34 C 0.6780(5) 0.5490(2) 0.3236(2) 0.0303(10) Uani 1 1 d . . . H9 H 0.634(5) 0.564(3) 0.287(2) 0.032(13) Uiso 1 1 d . . . C9 C 0.6272(5) 0.3458(2) 0.5227(2) 0.0307(10) Uani 1 1 d . . . C10 C 0.9727(5) 0.3344(3) 0.4374(2) 0.0386(11) Uani 1 1 d . . . H10 H 0.934(6) 0.346(3) 0.397(3) 0.048(15) Uiso 1 1 d . . . H11 H 1.020(6) 0.287(3) 0.427(2) 0.042(14) Uiso 1 1 d . . . H12 H 1.042(7) 0.377(4) 0.453(3) 0.08(2) Uiso 1 1 d . . . C11 C 0.7214(5) 0.3513(2) 0.4754(2) 0.0289(9) Uani 1 1 d . . . C27 C 0.1388(5) 0.1164(3) 0.3301(2) 0.0371(11) Uani 1 1 d . . . H13 H 0.092(6) 0.067(3) 0.336(2) 0.053(15) Uiso 1 1 d . . . C44 C 0.3035(5) 0.4119(2) 0.1796(2) 0.0337(10) Uani 1 1 d . . . C45 C 0.5555(5) 0.4424(2) 0.2148(2) 0.0326(10) Uani 1 1 d . . . C51 C 0.8140(5) 0.2799(3) 0.5834(2) 0.0362(11) Uani 1 1 d . . . C13 C 0.4775(6) 0.3790(3) 0.5167(3) 0.0427(12) Uani 1 1 d . . . H14 H 0.418(7) 0.353(3) 0.487(3) 0.059(17) Uiso 1 1 d . . . H15 H 0.483(8) 0.437(4) 0.507(3) 0.09(2) Uiso 1 1 d . . . H16 H 0.436(8) 0.376(4) 0.553(3) 0.08(2) Uiso 1 1 d . . . C38 C 0.3793(4) 0.4487(2) 0.32608(19) 0.0265(9) Uani 1 1 d . . . C28 C 0.1336(5) 0.2321(2) 0.2790(2) 0.0318(10) Uani 1 1 d . . . H17 H 0.096(5) 0.265(2) 0.250(2) 0.028(12) Uiso 1 1 d . . . C46 C 0.5611(4) 0.3856(2) 0.26483(19) 0.0260(9) Uani 1 1 d . . . C50 C 0.4700(5) 0.1730(2) 0.4898(2) 0.0365(11) Uani 1 1 d . . . C14 C 0.3197(7) 0.1975(3) 0.5058(3) 0.0479(14) Uani 1 1 d . . . H18 H 0.246(8) 0.151(4) 0.496(3) 0.08(2) Uiso 1 1 d . . . H19 H 0.283(7) 0.229(3) 0.480(3) 0.06(2) Uiso 1 1 d . . . H20 H 0.321(7) 0.227(4) 0.547(4) 0.09(2) Uiso 1 1 d . . . C47 C 0.4108(5) 0.4614(3) 0.1860(2) 0.0376(11) Uani 1 1 d . . . C39 C 0.0836(5) 0.4757(3) 0.3172(2) 0.0364(11) Uani 1 1 d . . . H21 H -0.015(6) 0.482(3) 0.315(2) 0.040(14) Uiso 1 1 d . . . C15 C 0.8608(8) 0.2401(4) 0.6397(3) 0.0528(15) Uani 1 1 d . . . H22 H 0.835(5) 0.269(3) 0.678(2) 0.036(13) Uiso 1 1 d . . . H23 H 0.959(10) 0.234(5) 0.647(4) 0.12(3) Uiso 1 1 d . . . H24 H 0.813(8) 0.194(4) 0.641(3) 0.08(2) Uiso 1 1 d . . . C16 C 0.6756(5) 0.3098(2) 0.5752(2) 0.0353(11) Uani 1 1 d . . . H25 H 0.608(7) 0.303(3) 0.609(3) 0.062(17) Uiso 1 1 d . . . C17 C 0.6875(6) 0.1033(3) 0.5189(2) 0.0408(12) Uani 1 1 d . . . C40 C 0.1321(5) 0.4045(2) 0.3132(2) 0.0312(10) Uani 1 1 d . . . H26 H 0.064(6) 0.361(3) 0.306(3) 0.056(16) Uiso 1 1 d . . . C18 C 0.5452(6) 0.1258(3) 0.5286(2) 0.0408(12) Uani 1 1 d . . . H27 H 0.496(6) 0.111(3) 0.567(3) 0.050(15) Uiso 1 1 d . . . C19 C 0.9058(5) 0.2891(3) 0.5374(2) 0.0355(11) Uani 1 1 d . . . H28 H 0.997(6) 0.267(3) 0.540(2) 0.040(14) Uiso 1 1 d . . . C35 C 0.8536(5) 0.5702(2) 0.4084(2) 0.0343(10) Uani 1 1 d . . . H29 H 0.932(6) 0.599(3) 0.432(3) 0.053(16) Uiso 1 1 d . . . C20 C 0.7511(6) 0.1311(2) 0.4700(2) 0.0366(11) Uani 1 1 d . . . H30 H 0.863(6) 0.116(3) 0.461(2) 0.048(15) Uiso 1 1 d . . . C41 C 0.1792(5) 0.5313(3) 0.3263(2) 0.0389(11) Uani 1 1 d . . . H31 H 0.152(5) 0.581(3) 0.332(2) 0.043(14) Uiso 1 1 d . . . C21 C 0.7675(9) 0.0487(4) 0.5598(4) 0.0621(18) Uani 1 1 d . . . H32 H 0.868(12) 0.040(5) 0.551(5) 0.14(4) Uiso 1 1 d . . . H33 H 0.767(10) -0.002(5) 0.533(4) 0.12(3) Uiso 1 1 d . . . H34 H 0.753(11) 0.051(5) 0.596(5) 0.13(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0375(7) 0.0568(8) 0.0584(9) 0.0098(6) -0.0169(6) 0.0024(6) Cl2 0.0614(9) 0.0422(7) 0.0713(10) 0.0230(7) -0.0122(8) -0.0051(6) O1 0.0338(18) 0.0435(19) 0.0362(19) -0.0031(15) -0.0037(15) -0.0068(15) O2 0.040(2) 0.0436(19) 0.043(2) 0.0072(15) 0.0060(16) -0.0118(16) C2 0.023(2) 0.030(2) 0.030(2) 0.0006(17) 0.0037(18) 0.0008(17) N1 0.030(2) 0.037(2) 0.047(3) -0.0070(18) 0.0073(18) 0.0002(17) C48 0.027(2) 0.035(2) 0.027(2) -0.0045(17) 0.0049(18) -0.0025(19) N2 0.027(2) 0.044(2) 0.043(2) -0.0106(18) 0.0016(17) 0.0012(18) C3 0.026(2) 0.036(2) 0.029(2) 0.0014(18) -0.0023(18) -0.0033(18) C4 0.020(2) 0.028(2) 0.028(2) -0.0010(16) 0.0061(17) 0.0054(16) C29 0.019(2) 0.027(2) 0.027(2) 0.0007(16) 0.0015(16) -0.0022(16) C42 0.019(2) 0.029(2) 0.029(2) 0.0006(17) 0.0017(17) -0.0021(16) C30 0.022(2) 0.027(2) 0.032(2) -0.0024(17) 0.0041(17) 0.0009(17) C31 0.024(2) 0.026(2) 0.033(2) -0.0030(17) 0.0026(18) 0.0000(17) C22 0.020(2) 0.029(2) 0.026(2) 0.0005(16) 0.0052(17) 0.0005(16) C49 0.023(2) 0.036(2) 0.031(2) -0.0005(19) 0.0037(18) -0.0031(19) C32 0.026(2) 0.035(2) 0.036(3) -0.0069(19) -0.0013(19) -0.0050(19) C23 0.0172(19) 0.033(2) 0.025(2) -0.0029(16) 0.0056(16) -0.0020(17) C36 0.025(2) 0.029(2) 0.041(3) -0.0016(19) 0.0046(19) -0.0031(19) C43 0.026(2) 0.035(2) 0.030(2) -0.0031(18) 0.0014(18) -0.0021(19) C24 0.024(2) 0.0239(19) 0.034(2) -0.0031(17) 0.0028(18) 0.0018(17) C37 0.024(2) 0.030(2) 0.026(2) -0.0016(17) 0.0009(17) -0.0007(17) C5 0.026(2) 0.029(2) 0.036(3) 0.0021(18) -0.0041(19) -0.0006(18) C1 0.0190(19) 0.026(2) 0.028(2) -0.0032(16) 0.0014(16) -0.0005(16) C25 0.029(2) 0.029(2) 0.032(2) -0.0029(18) 0.0049(19) -0.0006(18) C26 0.029(2) 0.030(2) 0.045(3) 0.003(2) 0.007(2) -0.0014(19) C6 0.030(2) 0.026(2) 0.033(2) 0.0016(17) 0.0001(19) -0.0020(18) C33 0.030(2) 0.029(2) 0.043(3) -0.006(2) 0.009(2) -0.0058(19) C7 0.026(2) 0.037(2) 0.044(3) -0.003(2) 0.002(2) -0.003(2) C8 0.030(3) 0.033(2) 0.046(3) 0.002(2) 0.001(2) 0.000(2) C34 0.025(2) 0.032(2) 0.035(3) -0.0029(19) 0.0063(19) 0.0007(18) C9 0.027(2) 0.039(2) 0.026(2) -0.0046(18) 0.0012(18) 0.0023(19) C10 0.028(2) 0.046(3) 0.041(3) 0.002(2) 0.000(2) 0.002(2) C11 0.022(2) 0.032(2) 0.032(2) 0.0001(18) -0.0002(18) -0.0029(18) C27 0.027(2) 0.035(2) 0.050(3) 0.001(2) 0.008(2) -0.006(2) C44 0.032(2) 0.036(2) 0.032(3) 0.0030(19) -0.0069(19) -0.001(2) C45 0.034(2) 0.032(2) 0.031(2) -0.0019(18) 0.002(2) -0.009(2) C51 0.041(3) 0.036(2) 0.030(3) 0.0006(19) -0.005(2) 0.000(2) C13 0.036(3) 0.058(3) 0.035(3) -0.005(2) 0.010(2) 0.005(2) C38 0.021(2) 0.028(2) 0.031(2) -0.0002(17) -0.0005(17) -0.0030(17) C28 0.024(2) 0.032(2) 0.039(3) -0.005(2) 0.0003(19) -0.0006(19) C46 0.0160(19) 0.034(2) 0.028(2) -0.0003(17) 0.0034(17) 0.0016(17) C50 0.040(3) 0.033(2) 0.037(3) 0.0078(19) 0.002(2) -0.003(2) C14 0.051(3) 0.050(3) 0.045(3) 0.006(3) 0.016(3) 0.003(3) C47 0.039(3) 0.039(3) 0.034(3) 0.005(2) -0.003(2) 0.000(2) C39 0.021(2) 0.035(2) 0.053(3) 0.000(2) 0.003(2) 0.0021(19) C15 0.061(4) 0.060(4) 0.037(3) 0.008(3) -0.003(3) 0.005(3) C16 0.039(3) 0.039(3) 0.028(3) 0.0009(19) 0.006(2) 0.000(2) C17 0.045(3) 0.035(3) 0.040(3) 0.006(2) -0.008(2) 0.001(2) C40 0.023(2) 0.035(2) 0.036(3) -0.0020(19) 0.0038(19) 0.0018(19) C18 0.045(3) 0.041(3) 0.036(3) 0.014(2) 0.002(2) -0.001(2) C19 0.031(3) 0.037(2) 0.038(3) 0.002(2) -0.002(2) 0.003(2) C35 0.027(2) 0.035(2) 0.041(3) -0.005(2) 0.004(2) -0.005(2) C20 0.042(3) 0.026(2) 0.040(3) 0.0033(19) -0.006(2) 0.001(2) C41 0.030(3) 0.033(2) 0.054(3) -0.004(2) 0.004(2) 0.005(2) C21 0.070(5) 0.055(4) 0.059(5) 0.021(3) -0.009(4) 0.009(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C44 1.706(5) . ? Cl2 C47 1.698(5) . ? O1 C43 1.212(5) . ? O2 C45 1.208(5) . ? C2 C23 1.373(6) . ? C2 C25 1.478(6) . ? C2 C6 1.485(6) . ? N1 C49 1.141(6) . ? C48 N2 1.145(6) . ? C48 C46 1.472(6) . ? C3 C19 1.393(6) . ? C3 C11 1.410(6) . ? C3 C10 1.506(7) . ? C4 C1 1.367(6) . ? C4 C31 1.480(6) . ? C4 C11 1.481(6) . ? C29 C30 1.509(6) . ? C29 C38 1.527(6) . ? C29 C1 1.536(6) . ? C29 C46 1.618(6) . ? C42 C49 1.486(6) . ? C42 C43 1.551(6) . ? C42 C46 1.596(6) . ? C42 C22 1.624(6) . ? C30 C34 1.387(6) . ? C30 C31 1.406(6) . ? C31 C32 1.397(6) . ? C22 C37 1.510(6) . ? C22 C24 1.517(6) . ? C22 C23 1.544(6) . ? C32 C35 1.388(7) . ? C32 H1 1.02(6) . ? C23 C1 1.443(6) . ? C36 C38 1.385(6) . ? C36 C41 1.410(6) . ? C36 H2 0.92(6) . ? C43 C44 1.476(6) . ? C24 C28 1.386(6) . ? C24 C25 1.402(6) . ? C37 C40 1.395(6) . ? C37 C38 1.401(6) . ? C5 C20 1.390(6) . ? C5 C6 1.425(6) . ? C5 C8 1.509(7) . ? C25 C26 1.394(6) . ? C26 C27 1.411(7) . ? C26 H3 1.01(5) . ? C6 C50 1.408(6) . ? C33 C35 1.389(7) . ? C33 C34 1.406(6) . ? C33 H4 1.00(4) . ? C7 C27 1.380(7) . ? C7 C28 1.408(7) . ? C7 H5 0.95(6) . ? C8 H6 1.05(6) . ? C8 H7 1.10(5) . ? C8 H8 1.00(6) . ? C34 H9 0.93(5) . ? C9 C16 1.391(7) . ? C9 C11 1.422(6) . ? C9 C13 1.513(7) . ? C10 H10 0.97(6) . ? C10 H11 1.03(5) . ? C10 H12 1.07(7) . ? C27 H13 1.03(6) . ? C44 C47 1.352(7) . ? C45 C47 1.483(7) . ? C45 C46 1.532(6) . ? C51 C19 1.392(7) . ? C51 C16 1.395(7) . ? C51 C15 1.492(7) . ? C13 H14 0.96(6) . ? C13 H15 1.11(7) . ? C13 H16 0.92(8) . ? C28 H17 0.94(5) . ? C50 C18 1.380(7) . ? C50 C14 1.531(8) . ? C14 H18 1.11(7) . ? C14 H19 0.87(7) . ? C14 H20 1.08(8) . ? C39 C41 1.364(7) . ? C39 C40 1.404(6) . ? C39 H21 0.92(5) . ? C15 H22 1.05(5) . ? C15 H23 0.91(9) . ? C15 H24 0.97(8) . ? C16 H25 1.03(6) . ? C17 C20 1.377(7) . ? C17 C18 1.414(7) . ? C17 C21 1.517(8) . ? C40 H26 1.02(6) . ? C18 H27 1.03(6) . ? C19 H28 0.94(5) . ? C35 H29 1.02(6) . ? C20 H30 1.11(5) . ? C41 H31 0.97(5) . ? C21 H32 0.98(11) . ? C21 H33 1.11(9) . ? C21 H34 0.83(11) . ? 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 C23 C2 C25 108.3(4) . . ? C23 C2 C6 131.8(4) . . ? C25 C2 C6 119.8(4) . . ? N2 C48 C46 179.0(5) . . ? C19 C3 C11 118.3(4) . . ? C19 C3 C10 119.4(4) . . ? C11 C3 C10 122.3(4) . . ? C1 C4 C31 108.1(4) . . ? C1 C4 C11 129.4(4) . . ? C31 C4 C11 122.4(4) . . ? C30 C29 C38 116.6(3) . . ? C30 C29 C1 103.5(3) . . ? C38 C29 C1 108.1(3) . . ? C30 C29 C46 115.4(3) . . ? C38 C29 C46 107.3(3) . . ? C1 C29 C46 105.1(3) . . ? C49 C42 C43 105.2(3) . . ? C49 C42 C46 111.7(3) . . ? C43 C42 C46 113.7(3) . . ? C49 C42 C22 109.7(3) . . ? C43 C42 C22 107.9(3) . . ? C46 C42 C22 108.5(3) . . ? C34 C30 C31 120.2(4) . . ? C34 C30 C29 131.6(4) . . ? C31 C30 C29 107.9(3) . . ? C32 C31 C30 120.8(4) . . ? C32 C31 C4 128.9(4) . . ? C30 C31 C4 110.2(4) . . ? C37 C22 C24 119.6(3) . . ? C37 C22 C23 110.6(3) . . ? C24 C22 C23 103.3(3) . . ? C37 C22 C42 104.9(3) . . ? C24 C22 C42 112.5(3) . . ? C23 C22 C42 105.1(3) . . ? N1 C49 C42 176.9(5) . . ? C35 C32 C31 118.6(4) . . ? C35 C32 H1 124(3) . . ? C31 C32 H1 118(3) . . ? C2 C23 C1 137.8(4) . . ? C2 C23 C22 109.8(4) . . ? C1 C23 C22 112.4(3) . . ? C38 C36 C41 118.7(4) . . ? C38 C36 H2 123(3) . . ? C41 C36 H2 118(3) . . ? O1 C43 C44 120.7(4) . . ? O1 C43 C42 120.9(4) . . ? C44 C43 C42 118.4(4) . . ? C28 C24 C25 121.2(4) . . ? C28 C24 C22 131.0(4) . . ? C25 C24 C22 107.9(4) . . ? C40 C37 C38 120.4(4) . . ? C40 C37 C22 125.2(4) . . ? C38 C37 C22 114.4(4) . . ? C20 C5 C6 119.3(4) . . ? C20 C5 C8 118.9(4) . . ? C6 C5 C8 121.8(4) . . ? C4 C1 C23 136.7(4) . . ? C4 C1 C29 110.2(3) . . ? C23 C1 C29 113.0(3) . . ? C26 C25 C24 120.8(4) . . ? C26 C25 C2 128.6(4) . . ? C24 C25 C2 110.5(4) . . ? C25 C26 C27 118.0(4) . . ? C25 C26 H3 122(3) . . ? C27 C26 H3 120(3) . . ? C50 C6 C5 118.7(4) . . ? C50 C6 C2 121.2(4) . . ? C5 C6 C2 119.6(4) . . ? C35 C33 C34 120.6(4) . . ? C35 C33 H4 120(2) . . ? C34 C33 H4 119(2) . . ? C27 C7 C28 121.5(5) . . ? C27 C7 H5 119(3) . . ? C28 C7 H5 120(3) . . ? C5 C8 H6 111(3) . . ? C5 C8 H7 113(3) . . ? H6 C8 H7 101(4) . . ? C5 C8 H8 112(3) . . ? H6 C8 H8 115(4) . . ? H7 C8 H8 104(4) . . ? C30 C34 C33 118.8(4) . . ? C30 C34 H9 122(3) . . ? C33 C34 H9 119(3) . . ? C16 C9 C11 118.8(4) . . ? C16 C9 C13 120.2(4) . . ? C11 C9 C13 121.0(4) . . ? C3 C10 H10 117(3) . . ? C3 C10 H11 112(3) . . ? H10 C10 H11 96(4) . . ? C3 C10 H12 106(4) . . ? H10 C10 H12 109(5) . . ? H11 C10 H12 118(5) . . ? C3 C11 C9 119.9(4) . . ? C3 C11 C4 121.3(4) . . ? C9 C11 C4 118.8(4) . . ? C7 C27 C26 120.6(4) . . ? C7 C27 H13 119(3) . . ? C26 C27 H13 120(3) . . ? C47 C44 C43 119.6(4) . . ? C47 C44 Cl1 123.3(4) . . ? C43 C44 Cl1 116.6(3) . . ? O2 C45 C47 121.9(4) . . ? O2 C45 C46 120.8(4) . . ? C47 C45 C46 117.3(4) . . ? C19 C51 C16 117.4(4) . . ? C19 C51 C15 121.8(5) . . ? C16 C51 C15 120.9(5) . . ? C9 C13 H14 109(4) . . ? C9 C13 H15 111(4) . . ? H14 C13 H15 113(5) . . ? C9 C13 H16 110(4) . . ? H14 C13 H16 109(6) . . ? H15 C13 H16 105(5) . . ? C36 C38 C37 120.5(4) . . ? C36 C38 C29 125.8(4) . . ? C37 C38 C29 113.7(4) . . ? C24 C28 C7 117.8(5) . . ? C24 C28 H17 118(3) . . ? C7 C28 H17 124(3) . . ? C48 C46 C45 107.3(3) . . ? C48 C46 C42 110.8(3) . . ? C45 C46 C42 113.8(3) . . ? C48 C46 C29 107.4(3) . . ? C45 C46 C29 108.4(3) . . ? C42 C46 C29 108.9(3) . . ? C18 C50 C6 120.1(5) . . ? C18 C50 C14 117.8(5) . . ? C6 C50 C14 122.0(4) . . ? C50 C14 H18 106(4) . . ? C50 C14 H19 111(4) . . ? H18 C14 H19 101(6) . . ? C50 C14 H20 114(4) . . ? H18 C14 H20 122(5) . . ? H19 C14 H20 101(6) . . ? C44 C47 C45 120.9(4) . . ? C44 C47 Cl2 122.6(4) . . ? C45 C47 Cl2 116.0(3) . . ? C41 C39 C40 121.1(4) . . ? C41 C39 H21 123(3) . . ? C40 C39 H21 116(3) . . ? C51 C15 H22 111(3) . . ? C51 C15 H23 115(6) . . ? H22 C15 H23 102(6) . . ? C51 C15 H24 111(4) . . ? H22 C15 H24 107(5) . . ? H23 C15 H24 110(7) . . ? C9 C16 C51 122.3(4) . . ? C9 C16 H25 121(3) . . ? C51 C16 H25 117(3) . . ? C20 C17 C18 117.9(4) . . ? C20 C17 C21 120.5(6) . . ? C18 C17 C21 121.6(5) . . ? C37 C40 C39 118.5(4) . . ? C37 C40 H26 118(3) . . ? C39 C40 H26 123(3) . . ? C50 C18 C17 121.5(5) . . ? C50 C18 H27 117(3) . . ? C17 C18 H27 122(3) . . ? C51 C19 C3 123.1(5) . . ? C51 C19 H28 120(3) . . ? C3 C19 H28 117(3) . . ? C32 C35 C33 121.0(4) . . ? C32 C35 H29 115(3) . . ? C33 C35 H29 124(3) . . ? C17 C20 C5 122.4(5) . . ? C17 C20 H30 121(3) . . ? C5 C20 H30 116(3) . . ? C39 C41 C36 120.7(4) . . ? C39 C41 H31 125(3) . . ? C36 C41 H31 115(3) . . ? C17 C21 H32 115(6) . . ? C17 C21 H33 105(5) . . ? H32 C21 H33 74(7) . . ? C17 C21 H34 116(7) . . ? H32 C21 H34 115(9) . . ? H33 C21 H34 124(8) . . ? 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 C38 C29 C30 C34 -58.1(6) . . . . ? C1 C29 C30 C34 -176.7(4) . . . . ? C46 C29 C30 C34 69.1(6) . . . . ? C38 C29 C30 C31 115.4(4) . . . . ? C1 C29 C30 C31 -3.1(4) . . . . ? C46 C29 C30 C31 -117.3(4) . . . . ? C34 C30 C31 C32 -0.2(6) . . . . ? C29 C30 C31 C32 -174.7(4) . . . . ? C34 C30 C31 C4 176.9(4) . . . . ? C29 C30 C31 C4 2.5(5) . . . . ? C1 C4 C31 C32 176.1(4) . . . . ? C11 C4 C31 C32 -1.0(7) . . . . ? C1 C4 C31 C30 -0.8(5) . . . . ? C11 C4 C31 C30 -177.8(4) . . . . ? C49 C42 C22 C37 -176.7(3) . . . . ? C43 C42 C22 C37 -62.7(4) . . . . ? C46 C42 C22 C37 61.0(4) . . . . ? C49 C42 C22 C24 -45.2(5) . . . . ? C43 C42 C22 C24 68.9(4) . . . . ? C46 C42 C22 C24 -167.5(3) . . . . ? C49 C42 C22 C23 66.6(4) . . . . ? C43 C42 C22 C23 -179.3(3) . . . . ? C46 C42 C22 C23 -55.7(4) . . . . ? C43 C42 C49 N1 -13(9) . . . . ? C46 C42 C49 N1 -137(9) . . . . ? C22 C42 C49 N1 103(9) . . . . ? C30 C31 C32 C35 -0.8(7) . . . . ? C4 C31 C32 C35 -177.4(4) . . . . ? C25 C2 C23 C1 179.2(5) . . . . ? C6 C2 C23 C1 -4.3(9) . . . . ? C25 C2 C23 C22 -1.8(5) . . . . ? C6 C2 C23 C22 174.7(4) . . . . ? C37 C22 C23 C2 132.9(4) . . . . ? C24 C22 C23 C2 3.8(4) . . . . ? C42 C22 C23 C2 -114.4(4) . . . . ? C37 C22 C23 C1 -47.8(4) . . . . ? C24 C22 C23 C1 -176.9(3) . . . . ? C42 C22 C23 C1 64.9(4) . . . . ? C49 C42 C43 O1 32.3(5) . . . . ? C46 C42 C43 O1 154.9(4) . . . . ? C22 C42 C43 O1 -84.7(5) . . . . ? C49 C42 C43 C44 -149.4(4) . . . . ? C46 C42 C43 C44 -26.9(5) . . . . ? C22 C42 C43 C44 93.6(4) . . . . ? C37 C22 C24 C28 53.0(7) . . . . ? C23 C22 C24 C28 176.3(4) . . . . ? C42 C22 C24 C28 -70.8(6) . . . . ? C37 C22 C24 C25 -127.7(4) . . . . ? C23 C22 C24 C25 -4.4(4) . . . . ? C42 C22 C24 C25 108.5(4) . . . . ? C24 C22 C37 C40 -11.4(6) . . . . ? C23 C22 C37 C40 -131.2(4) . . . . ? C42 C22 C37 C40 116.0(5) . . . . ? C24 C22 C37 C38 171.4(4) . . . . ? C23 C22 C37 C38 51.6(5) . . . . ? C42 C22 C37 C38 -61.2(4) . . . . ? C31 C4 C1 C23 -178.1(5) . . . . ? C11 C4 C1 C23 -1.3(8) . . . . ? C31 C4 C1 C29 -1.3(5) . . . . ? C11 C4 C1 C29 175.5(4) . . . . ? C2 C23 C1 C4 -10.0(9) . . . . ? C22 C23 C1 C4 171.1(5) . . . . ? C2 C23 C1 C29 173.3(5) . . . . ? C22 C23 C1 C29 -5.7(5) . . . . ? C30 C29 C1 C4 2.7(4) . . . . ? C38 C29 C1 C4 -121.5(4) . . . . ? C46 C29 C1 C4 124.1(3) . . . . ? C30 C29 C1 C23 -179.7(3) . . . . ? C38 C29 C1 C23 56.1(4) . . . . ? C46 C29 C1 C23 -58.3(4) . . . . ? C28 C24 C25 C26 3.5(7) . . . . ? C22 C24 C25 C26 -175.9(4) . . . . ? C28 C24 C25 C2 -177.1(4) . . . . ? C22 C24 C25 C2 3.6(5) . . . . ? C23 C2 C25 C26 178.3(4) . . . . ? C6 C2 C25 C26 1.3(7) . . . . ? C23 C2 C25 C24 -1.1(5) . . . . ? C6 C2 C25 C24 -178.1(4) . . . . ? C24 C25 C26 C27 -2.3(7) . . . . ? C2 C25 C26 C27 178.4(4) . . . . ? C20 C5 C6 C50 1.9(6) . . . . ? C8 C5 C6 C50 178.6(4) . . . . ? C20 C5 C6 C2 -170.1(4) . . . . ? C8 C5 C6 C2 6.6(6) . . . . ? C23 C2 C6 C50 124.2(5) . . . . ? C25 C2 C6 C50 -59.6(6) . . . . ? C23 C2 C6 C5 -64.1(6) . . . . ? C25 C2 C6 C5 112.1(5) . . . . ? C31 C30 C34 C33 1.2(6) . . . . ? C29 C30 C34 C33 174.1(4) . . . . ? C35 C33 C34 C30 -1.2(7) . . . . ? C19 C3 C11 C9 4.7(6) . . . . ? C10 C3 C11 C9 -175.1(4) . . . . ? C19 C3 C11 C4 -178.0(4) . . . . ? C10 C3 C11 C4 2.2(7) . . . . ? C16 C9 C11 C3 -4.4(6) . . . . ? C13 C9 C11 C3 175.0(4) . . . . ? C16 C9 C11 C4 178.2(4) . . . . ? C13 C9 C11 C4 -2.4(6) . . . . ? C1 C4 C11 C3 115.0(5) . . . . ? C31 C4 C11 C3 -68.6(6) . . . . ? C1 C4 C11 C9 -67.7(6) . . . . ? C31 C4 C11 C9 108.8(5) . . . . ? C28 C7 C27 C26 2.0(8) . . . . ? C25 C26 C27 C7 -0.4(7) . . . . ? O1 C43 C44 C47 -148.2(5) . . . . ? C42 C43 C44 C47 33.5(6) . . . . ? O1 C43 C44 Cl1 23.3(6) . . . . ? C42 C43 C44 Cl1 -155.0(3) . . . . ? C41 C36 C38 C37 -0.9(7) . . . . ? C41 C36 C38 C29 178.2(4) . . . . ? C40 C37 C38 C36 2.0(7) . . . . ? C22 C37 C38 C36 179.3(4) . . . . ? C40 C37 C38 C29 -177.3(4) . . . . ? C22 C37 C38 C29 0.1(5) . . . . ? C30 C29 C38 C36 11.3(6) . . . . ? C1 C29 C38 C36 127.3(5) . . . . ? C46 C29 C38 C36 -119.9(5) . . . . ? C30 C29 C38 C37 -169.5(4) . . . . ? C1 C29 C38 C37 -53.5(5) . . . . ? C46 C29 C38 C37 59.3(4) . . . . ? C25 C24 C28 C7 -1.9(7) . . . . ? C22 C24 C28 C7 177.3(4) . . . . ? C27 C7 C28 C24 -0.8(7) . . . . ? N2 C48 C46 C45 11(33) . . . . ? N2 C48 C46 C42 136(33) . . . . ? N2 C48 C46 C29 -105(33) . . . . ? O2 C45 C46 C48 -23.8(6) . . . . ? C47 C45 C46 C48 157.9(4) . . . . ? O2 C45 C46 C42 -146.7(4) . . . . ? C47 C45 C46 C42 34.9(5) . . . . ? O2 C45 C46 C29 92.0(5) . . . . ? C47 C45 C46 C29 -86.4(5) . . . . ? C49 C42 C46 C48 -8.4(5) . . . . ? C43 C42 C46 C48 -127.3(4) . . . . ? C22 C42 C46 C48 112.7(4) . . . . ? C49 C42 C46 C45 112.6(4) . . . . ? C43 C42 C46 C45 -6.3(5) . . . . ? C22 C42 C46 C45 -126.3(4) . . . . ? C49 C42 C46 C29 -126.3(4) . . . . ? C43 C42 C46 C29 114.8(4) . . . . ? C22 C42 C46 C29 -5.2(4) . . . . ? C30 C29 C46 C48 55.3(5) . . . . ? C38 C29 C46 C48 -172.8(3) . . . . ? C1 C29 C46 C48 -57.9(4) . . . . ? C30 C29 C46 C45 -60.3(4) . . . . ? C38 C29 C46 C45 71.5(4) . . . . ? C1 C29 C46 C45 -173.6(3) . . . . ? C30 C29 C46 C42 175.4(3) . . . . ? C38 C29 C46 C42 -52.8(4) . . . . ? C1 C29 C46 C42 62.1(4) . . . . ? C5 C6 C50 C18 -2.5(7) . . . . ? C2 C6 C50 C18 169.3(4) . . . . ? C5 C6 C50 C14 175.0(5) . . . . ? C2 C6 C50 C14 -13.2(7) . . . . ? C43 C44 C47 C45 -3.1(7) . . . . ? Cl1 C44 C47 C45 -173.9(4) . . . . ? C43 C44 C47 Cl2 168.3(4) . . . . ? Cl1 C44 C47 Cl2 -2.5(7) . . . . ? O2 C45 C47 C44 149.4(5) . . . . ? C46 C45 C47 C44 -32.3(7) . . . . ? O2 C45 C47 Cl2 -22.5(6) . . . . ? C46 C45 C47 Cl2 155.8(3) . . . . ? C11 C9 C16 C51 1.1(7) . . . . ? C13 C9 C16 C51 -178.4(5) . . . . ? C19 C51 C16 C9 1.8(7) . . . . ? C15 C51 C16 C9 -178.4(5) . . . . ? C38 C37 C40 C39 -1.3(7) . . . . ? C22 C37 C40 C39 -178.4(4) . . . . ? C41 C39 C40 C37 -0.4(7) . . . . ? C6 C50 C18 C17 0.8(8) . . . . ? C14 C50 C18 C17 -176.8(5) . . . . ? C20 C17 C18 C50 1.5(8) . . . . ? C21 C17 C18 C50 -177.0(5) . . . . ? C16 C51 C19 C3 -1.5(7) . . . . ? C15 C51 C19 C3 178.8(5) . . . . ? C11 C3 C19 C51 -1.8(7) . . . . ? C10 C3 C19 C51 178.0(5) . . . . ? C31 C32 C35 C33 0.8(7) . . . . ? C34 C33 C35 C32 0.2(7) . . . . ? C18 C17 C20 C5 -2.1(7) . . . . ? C21 C17 C20 C5 176.4(5) . . . . ? C6 C5 C20 C17 0.5(7) . . . . ? C8 C5 C20 C17 -176.3(5) . . . . ? C40 C39 C41 C36 1.4(8) . . . . ? C38 C36 C41 C39 -0.8(7) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.39 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.618 _refine_diff_density_min -0.788 _refine_diff_density_rms 0.105 _database_code_depnum_ccdc_archive 'CCDC 960645' ####################################################################### # # 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_ydkr _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C45 H40 O3' _chemical_formula_weight 628.77 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' 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 8.2660(9) _cell_length_b 18.710(2) _cell_length_c 21.637(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.739(3) _cell_angle_gamma 90.00 _cell_volume 3346.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9628 _exptl_absorpt_correction_T_max 0.9849 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31780 _diffrn_reflns_av_R_equivalents 0.2191 _diffrn_reflns_av_sigmaI/netI 0.1914 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.38 _reflns_number_total 7546 _reflns_number_gt 3258 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)' _computing_publication_material 'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)' _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^)+(0.1184P)^2^+1.9929P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7546 _refine_ls_number_parameters 441 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2344 _refine_ls_R_factor_gt 0.1079 _refine_ls_wR_factor_ref 0.3123 _refine_ls_wR_factor_gt 0.2201 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.4494(4) 0.32213(19) 0.47006(15) 0.0339(9) Uani 1 1 d . . . O2 O 0.3858(4) 0.38565(18) 0.50570(15) 0.0307(9) Uani 1 1 d . . . C3 C 0.2893(6) 0.2833(3) 0.7041(2) 0.0288(12) Uani 1 1 d . . . C4 C 0.2092(6) 0.0789(3) 0.6678(2) 0.0320(12) Uani 1 1 d . . . H1 H 0.0959 0.0733 0.6728 0.038 Uiso 1 1 calc R . . C5 C 0.5687(6) 0.1602(3) 0.5124(2) 0.0331(12) Uani 1 1 d . . . C6 C 0.4286(6) 0.3184(3) 0.6017(2) 0.0274(12) Uani 1 1 d . . . C7 C 0.6442(6) 0.3948(3) 0.5564(2) 0.0245(11) Uani 1 1 d . . . C8 C 0.4957(5) 0.1858(3) 0.5705(2) 0.0278(12) Uani 1 1 d . . . C9 C 0.1967(6) 0.1946(3) 0.8031(2) 0.0355(13) Uani 1 1 d . . . C10 C 0.4642(6) 0.3883(3) 0.5680(2) 0.0271(12) Uani 1 1 d . . . C11 C 0.5412(6) 0.0952(3) 0.6531(2) 0.0316(12) Uani 1 1 d . . . C12 C 0.3601(6) 0.2053(3) 0.7891(2) 0.0313(12) Uani 1 1 d . . . H2 H 0.4405 0.1818 0.8134 0.038 Uiso 1 1 calc R . . C13 C 0.7035(6) 0.3376(3) 0.5232(2) 0.0253(11) Uani 1 1 d . . . C14 C 0.2745(6) 0.5561(3) 0.6368(2) 0.0327(13) Uani 1 1 d . . . H3 H 0.2619 0.6061 0.6311 0.039 Uiso 1 1 calc R . . C15 C 0.3774(5) 0.4442(3) 0.6045(2) 0.0282(12) Uani 1 1 d . . . C16 C 0.3422(5) 0.3328(3) 0.6537(2) 0.0279(12) Uani 1 1 d . . . C17 C 0.4326(6) 0.1361(3) 0.6174(2) 0.0309(12) Uani 1 1 d . . . C18 C 0.2635(6) 0.1274(3) 0.6243(2) 0.0275(11) Uani 1 1 d . . . C19 C 0.4075(6) 0.2488(3) 0.7415(2) 0.0297(12) Uani 1 1 d . . . C20 C 0.2047(6) 0.5236(3) 0.6868(2) 0.0310(12) Uani 1 1 d . . . H4 H 0.1432 0.5518 0.7145 0.037 Uiso 1 1 calc R . . C21 C 0.0821(6) 0.2289(3) 0.7651(3) 0.0364(13) Uani 1 1 d . . . H5 H -0.0294 0.2216 0.7732 0.044 Uiso 1 1 calc R . . C22 C 0.5856(6) 0.2620(3) 0.7319(2) 0.0335(13) Uani 1 1 d . . . H6 H 0.6491 0.2315 0.7599 0.050 Uiso 1 1 calc R . . H7 H 0.6105 0.3123 0.7404 0.050 Uiso 1 1 calc R . . H8 H 0.6129 0.2509 0.6890 0.050 Uiso 1 1 calc R . . C23 C 0.3140(6) 0.0380(3) 0.7046(2) 0.0326(13) Uani 1 1 d . . . C24 C 0.4910(5) 0.2593(3) 0.5675(2) 0.0272(12) Uani 1 1 d . . . C25 C 0.5720(6) 0.2849(3) 0.5075(2) 0.0296(12) Uani 1 1 d . . . C26 C 0.9081(6) 0.4471(3) 0.5580(2) 0.0356(13) Uani 1 1 d . . . H9 H 0.9790 0.4846 0.5703 0.043 Uiso 1 1 calc R . . C27 C 0.6107(6) 0.2174(3) 0.4745(2) 0.0322(13) Uani 1 1 d . . . C28 C 0.3632(5) 0.5170(3) 0.5946(2) 0.0262(11) Uani 1 1 d . . . H10 H 0.4124 0.5394 0.5602 0.031 Uiso 1 1 calc R . . C29 C 0.1239(6) 0.2728(3) 0.7164(2) 0.0319(12) Uani 1 1 d . . . C30 C 0.9687(6) 0.3901(3) 0.5249(2) 0.0315(12) Uani 1 1 d . . . H11 H 1.0800 0.3889 0.5145 0.038 Uiso 1 1 calc R . . C31 C 0.4790(6) 0.0471(3) 0.6959(2) 0.0348(13) Uani 1 1 d . . . H12 H 0.5524 0.0193 0.7200 0.042 Uiso 1 1 calc R . . C32 C 0.3073(5) 0.4105(2) 0.6556(2) 0.0251(11) Uani 1 1 d . . . C33 C 0.8660(6) 0.3341(3) 0.5067(2) 0.0323(12) Uani 1 1 d . . . H13 H 0.9059 0.2947 0.4838 0.039 Uiso 1 1 calc R . . C34 C 0.7010(7) 0.1353(3) 0.3976(3) 0.0464(15) Uani 1 1 d . . . H14 H 0.7472 0.1266 0.3584 0.056 Uiso 1 1 calc R . . C35 C 0.7232(6) 0.1031(3) 0.6469(3) 0.0408(14) Uani 1 1 d . . . H15 H 0.7494 0.1128 0.6037 0.061 Uiso 1 1 calc R . . H16 H 0.7765 0.0588 0.6602 0.061 Uiso 1 1 calc R . . H17 H 0.7612 0.1428 0.6729 0.061 Uiso 1 1 calc R . . C36 C 0.2512(7) -0.0142(3) 0.7519(3) 0.0438(15) Uani 1 1 d . . . H18 H 0.2017 0.0122 0.7859 0.066 Uiso 1 1 calc R . . H19 H 0.3410 -0.0432 0.7680 0.066 Uiso 1 1 calc R . . H20 H 0.1702 -0.0454 0.7324 0.066 Uiso 1 1 calc R . . C37 C 0.6757(7) 0.2050(3) 0.4165(2) 0.0403(14) Uani 1 1 d . . . H21 H 0.7023 0.2438 0.3902 0.048 Uiso 1 1 calc R . . C38 C 0.1474(7) 0.1496(3) 0.8578(3) 0.0463(15) Uani 1 1 d . . . H22 H 0.2435 0.1376 0.8827 0.069 Uiso 1 1 calc R . . H23 H 0.0958 0.1055 0.8430 0.069 Uiso 1 1 calc R . . H24 H 0.0710 0.1764 0.8831 0.069 Uiso 1 1 calc R . . C39 C 0.7457(6) 0.4508(3) 0.5738(2) 0.0295(12) Uani 1 1 d . . . H25 H 0.7051 0.4906 0.5960 0.035 Uiso 1 1 calc R . . C40 C 0.6607(7) 0.0780(3) 0.4346(3) 0.0491(16) Uani 1 1 d . . . H26 H 0.6770 0.0306 0.4204 0.059 Uiso 1 1 calc R . . C41 C 0.2212(6) 0.4500(3) 0.6983(2) 0.0297(12) Uani 1 1 d . . . H27 H 0.1756 0.4283 0.7338 0.036 Uiso 1 1 calc R . . C42 C 0.5950(7) 0.0901(3) 0.4937(3) 0.0396(14) Uani 1 1 d . . . H28 H 0.5694 0.0512 0.5200 0.047 Uiso 1 1 calc R . . C43 C 0.1455(6) 0.1693(3) 0.5839(3) 0.0362(13) Uani 1 1 d . . . H29 H 0.0349 0.1531 0.5918 0.054 Uiso 1 1 calc R . . H30 H 0.1709 0.1615 0.5403 0.054 Uiso 1 1 calc R . . H31 H 0.1546 0.2203 0.5936 0.054 Uiso 1 1 calc R . . C44 C 1.1274(7) 0.0855(3) 0.3835(3) 0.0496(16) Uani 1 1 d . . . O3 O 1.0631(6) 0.0683(3) 0.3349(2) 0.0790(16) Uani 1 1 d . . . C46 C 1.0923(8) 0.0493(4) 0.4429(3) 0.0617(19) Uani 1 1 d . . . H32 H 1.0293 0.0058 0.4348 0.093 Uiso 1 1 calc R . . H33 H 1.0302 0.0815 0.4693 0.093 Uiso 1 1 calc R . . H34 H 1.1942 0.0366 0.4638 0.093 Uiso 1 1 calc R . . C47 C 1.2434(11) 0.1443(5) 0.3847(4) 0.117(4) Uani 1 1 d . . . H35 H 1.3451 0.1281 0.4038 0.176 Uiso 1 1 calc R . . H36 H 1.1995 0.1841 0.4087 0.176 Uiso 1 1 calc R . . H37 H 1.2636 0.1603 0.3423 0.176 Uiso 1 1 calc R . . C48 C -0.0091(6) 0.3072(3) 0.6785(2) 0.0347(13) Uani 1 1 d . . . H38 H -0.0908 0.2713 0.6675 0.052 Uiso 1 1 calc R . . H39 H 0.0364 0.3274 0.6406 0.052 Uiso 1 1 calc R . . H40 H -0.0593 0.3454 0.7025 0.052 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.036(2) 0.040(2) 0.0251(18) -0.0039(17) 0.0055(16) -0.0011(17) O2 0.0331(19) 0.033(2) 0.0262(18) 0.0011(16) 0.0018(15) 0.0045(16) C3 0.030(3) 0.026(3) 0.030(3) 0.000(2) 0.008(2) -0.003(2) C4 0.033(3) 0.032(3) 0.030(3) -0.003(3) 0.011(2) -0.001(2) C5 0.037(3) 0.030(3) 0.033(3) -0.001(3) 0.008(2) -0.003(2) C6 0.026(2) 0.029(3) 0.027(3) 0.001(2) 0.002(2) -0.007(2) C7 0.031(3) 0.026(3) 0.016(2) 0.008(2) 0.000(2) -0.002(2) C8 0.024(2) 0.025(3) 0.035(3) -0.001(2) 0.000(2) 0.000(2) C9 0.042(3) 0.025(3) 0.039(3) -0.002(3) 0.009(3) -0.003(2) C10 0.030(3) 0.030(3) 0.021(3) 0.000(2) 0.002(2) -0.002(2) C11 0.030(3) 0.031(3) 0.033(3) -0.007(3) 0.004(2) 0.001(2) C12 0.025(3) 0.027(3) 0.042(3) -0.002(3) 0.005(2) 0.000(2) C13 0.030(3) 0.031(3) 0.015(2) 0.001(2) 0.004(2) -0.007(2) C14 0.036(3) 0.026(3) 0.036(3) 0.006(3) 0.003(2) 0.000(2) C15 0.020(2) 0.027(3) 0.037(3) 0.003(2) 0.002(2) 0.001(2) C16 0.022(2) 0.028(3) 0.034(3) -0.003(2) 0.001(2) -0.003(2) C17 0.039(3) 0.019(3) 0.035(3) -0.007(2) 0.012(3) -0.007(2) C18 0.028(3) 0.019(3) 0.035(3) -0.003(2) 0.002(2) -0.003(2) C19 0.026(3) 0.025(3) 0.039(3) -0.005(2) 0.009(2) 0.000(2) C20 0.030(3) 0.027(3) 0.036(3) -0.008(3) 0.002(2) 0.007(2) C21 0.028(3) 0.031(3) 0.050(3) -0.003(3) 0.011(3) -0.008(2) C22 0.028(3) 0.040(3) 0.033(3) 0.006(3) 0.001(2) 0.005(2) C23 0.038(3) 0.031(3) 0.029(3) -0.009(2) 0.007(2) -0.011(2) C24 0.020(2) 0.025(3) 0.037(3) 0.006(2) 0.009(2) -0.003(2) C25 0.033(3) 0.027(3) 0.029(3) 0.006(2) 0.005(2) -0.001(2) C26 0.037(3) 0.039(3) 0.031(3) 0.010(3) 0.002(2) -0.006(3) C27 0.029(3) 0.038(3) 0.030(3) 0.000(3) 0.002(2) -0.003(2) C28 0.028(3) 0.025(3) 0.026(3) 0.002(2) 0.002(2) -0.004(2) C29 0.025(3) 0.029(3) 0.042(3) -0.003(3) 0.018(2) -0.002(2) C30 0.026(3) 0.044(3) 0.025(3) 0.007(3) 0.002(2) -0.007(2) C31 0.040(3) 0.023(3) 0.041(3) 0.010(3) -0.005(3) 0.010(2) C32 0.026(3) 0.018(3) 0.031(3) 0.000(2) 0.002(2) -0.002(2) C33 0.034(3) 0.038(3) 0.025(3) 0.006(3) 0.008(2) 0.004(2) C34 0.063(4) 0.043(4) 0.034(3) -0.011(3) 0.024(3) 0.000(3) C35 0.029(3) 0.046(4) 0.047(3) 0.002(3) -0.005(3) 0.005(3) C36 0.052(3) 0.035(3) 0.045(4) 0.008(3) 0.009(3) -0.004(3) C37 0.052(3) 0.037(4) 0.033(3) 0.000(3) 0.016(3) 0.003(3) C38 0.052(4) 0.036(4) 0.051(4) 0.009(3) 0.013(3) -0.010(3) C39 0.031(3) 0.027(3) 0.031(3) 0.000(2) 0.008(2) -0.003(2) C40 0.058(4) 0.036(4) 0.054(4) -0.011(3) 0.011(3) -0.001(3) C41 0.027(3) 0.026(3) 0.036(3) 0.003(2) 0.000(2) -0.005(2) C42 0.052(3) 0.032(3) 0.036(3) -0.007(3) 0.010(3) -0.006(3) C43 0.028(3) 0.031(3) 0.050(3) 0.000(3) 0.004(2) -0.001(2) C44 0.044(3) 0.038(4) 0.066(4) 0.002(3) 0.016(3) 0.005(3) O3 0.082(3) 0.102(4) 0.054(3) -0.023(3) 0.017(3) -0.039(3) C46 0.071(4) 0.056(5) 0.059(4) -0.001(4) 0.023(4) -0.017(4) C47 0.129(7) 0.113(8) 0.107(7) 0.079(6) -0.053(6) -0.080(6) C48 0.028(3) 0.036(3) 0.041(3) 0.006(3) 0.009(2) -0.004(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C25 1.465(6) . ? O1 O2 1.515(5) . ? O2 C10 1.489(5) . ? C3 C29 1.410(6) . ? C3 C19 1.417(7) . ? C3 C16 1.501(7) . ? C4 C18 1.385(7) . ? C4 C23 1.398(7) . ? C4 H1 0.9500 . ? C5 C42 1.390(7) . ? C5 C27 1.394(7) . ? C5 C8 1.481(7) . ? C6 C16 1.367(7) . ? C6 C24 1.429(7) . ? C6 C10 1.528(7) . ? C7 C13 1.381(7) . ? C7 C39 1.391(6) . ? C7 C10 1.518(6) . ? C8 C24 1.378(7) . ? C8 C17 1.477(7) . ? C9 C21 1.400(7) . ? C9 C12 1.402(7) . ? C9 C38 1.514(7) . ? C10 C15 1.498(7) . ? C11 C31 1.394(7) . ? C11 C17 1.404(7) . ? C11 C35 1.520(7) . ? C12 C19 1.374(7) . ? C12 H2 0.9500 . ? C13 C33 1.396(6) . ? C13 C25 1.504(7) . ? C14 C20 1.374(7) . ? C14 C28 1.387(7) . ? C14 H3 0.9500 . ? C15 C28 1.384(7) . ? C15 C32 1.405(7) . ? C16 C32 1.481(7) . ? C17 C18 1.417(7) . ? C18 C43 1.519(7) . ? C19 C22 1.510(6) . ? C20 C41 1.407(7) . ? C20 H4 0.9500 . ? C21 C29 1.385(7) . ? C21 H5 0.9500 . ? C22 H6 0.9800 . ? C22 H7 0.9800 . ? C22 H8 0.9800 . ? C23 C31 1.390(7) . ? C23 C36 1.511(7) . ? C24 C25 1.545(7) . ? C25 C27 1.487(7) . ? C26 C30 1.382(7) . ? C26 C39 1.391(7) . ? C26 H9 0.9500 . ? C27 C37 1.392(7) . ? C28 H10 0.9500 . ? C29 C48 1.507(7) . ? C30 C33 1.403(7) . ? C30 H11 0.9500 . ? C31 H12 0.9500 . ? C32 C41 1.388(7) . ? C33 H13 0.9500 . ? C34 C40 1.381(8) . ? C34 C37 1.382(8) . ? C34 H14 0.9500 . ? C35 H15 0.9800 . ? C35 H16 0.9800 . ? C35 H17 0.9800 . ? C36 H18 0.9800 . ? C36 H19 0.9800 . ? C36 H20 0.9800 . ? C37 H21 0.9500 . ? C38 H22 0.9800 . ? C38 H23 0.9800 . ? C38 H24 0.9800 . ? C39 H25 0.9500 . ? C40 C42 1.412(8) . ? C40 H26 0.9500 . ? C41 H27 0.9500 . ? C42 H28 0.9500 . ? C43 H29 0.9800 . ? C43 H30 0.9800 . ? C43 H31 0.9800 . ? C44 O3 1.216(7) . ? C44 C47 1.460(9) . ? C44 C46 1.484(8) . ? C46 H32 0.9800 . ? C46 H33 0.9800 . ? C46 H34 0.9800 . ? C47 H35 0.9800 . ? C47 H36 0.9800 . ? C47 H37 0.9800 . ? C48 H38 0.9800 . ? C48 H39 0.9800 . ? C48 H40 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C25 O1 O2 109.5(3) . . ? C10 O2 O1 109.7(3) . . ? C29 C3 C19 119.5(5) . . ? C29 C3 C16 121.0(4) . . ? C19 C3 C16 119.4(4) . . ? C18 C4 C23 122.8(5) . . ? C18 C4 H1 118.6 . . ? C23 C4 H1 118.6 . . ? C42 C5 C27 120.8(5) . . ? C42 C5 C8 128.2(5) . . ? C27 C5 C8 111.0(5) . . ? C16 C6 C24 140.7(5) . . ? C16 C6 C10 109.2(4) . . ? C24 C6 C10 110.0(4) . . ? C13 C7 C39 120.5(4) . . ? C13 C7 C10 112.3(4) . . ? C39 C7 C10 127.2(4) . . ? C24 C8 C17 130.6(5) . . ? C24 C8 C5 107.1(4) . . ? C17 C8 C5 122.1(4) . . ? C21 C9 C12 117.0(5) . . ? C21 C9 C38 121.8(5) . . ? C12 C9 C38 121.2(5) . . ? O2 C10 C15 107.1(4) . . ? O2 C10 C7 105.6(4) . . ? C15 C10 C7 120.6(4) . . ? O2 C10 C6 108.6(4) . . ? C15 C10 C6 104.5(4) . . ? C7 C10 C6 110.0(4) . . ? C31 C11 C17 118.6(4) . . ? C31 C11 C35 119.7(5) . . ? C17 C11 C35 121.7(5) . . ? C19 C12 C9 122.1(5) . . ? C19 C12 H2 119.0 . . ? C9 C12 H2 119.0 . . ? C7 C13 C33 121.2(5) . . ? C7 C13 C25 111.5(4) . . ? C33 C13 C25 127.3(5) . . ? C20 C14 C28 121.2(5) . . ? C20 C14 H3 119.4 . . ? C28 C14 H3 119.4 . . ? C28 C15 C32 122.0(5) . . ? C28 C15 C10 130.2(5) . . ? C32 C15 C10 107.8(4) . . ? C6 C16 C32 108.7(4) . . ? C6 C16 C3 129.5(5) . . ? C32 C16 C3 121.8(4) . . ? C11 C17 C18 120.2(5) . . ? C11 C17 C8 119.5(4) . . ? C18 C17 C8 120.2(4) . . ? C4 C18 C17 118.4(5) . . ? C4 C18 C43 121.2(4) . . ? C17 C18 C43 120.4(4) . . ? C12 C19 C3 119.8(4) . . ? C12 C19 C22 119.3(4) . . ? C3 C19 C22 120.8(4) . . ? C14 C20 C41 122.1(5) . . ? C14 C20 H4 119.0 . . ? C41 C20 H4 119.0 . . ? C29 C21 C9 123.0(5) . . ? C29 C21 H5 118.5 . . ? C9 C21 H5 118.5 . . ? C19 C22 H6 109.5 . . ? C19 C22 H7 109.5 . . ? H6 C22 H7 109.5 . . ? C19 C22 H8 109.5 . . ? H6 C22 H8 109.5 . . ? H7 C22 H8 109.5 . . ? C31 C23 C4 117.3(5) . . ? C31 C23 C36 121.1(5) . . ? C4 C23 C36 121.6(5) . . ? C8 C24 C6 139.3(5) . . ? C8 C24 C25 109.6(4) . . ? C6 C24 C25 111.0(4) . . ? O1 C25 C27 106.9(4) . . ? O1 C25 C13 107.8(4) . . ? C27 C25 C13 120.4(4) . . ? O1 C25 C24 107.9(4) . . ? C27 C25 C24 103.8(4) . . ? C13 C25 C24 109.4(4) . . ? C30 C26 C39 121.5(5) . . ? C30 C26 H9 119.3 . . ? C39 C26 H9 119.3 . . ? C37 C27 C5 120.3(5) . . ? C37 C27 C25 131.5(5) . . ? C5 C27 C25 108.2(4) . . ? C15 C28 C14 117.4(5) . . ? C15 C28 H10 121.3 . . ? C14 C28 H10 121.3 . . ? C21 C29 C3 118.6(5) . . ? C21 C29 C48 118.8(4) . . ? C3 C29 C48 122.7(5) . . ? C26 C30 C33 120.0(5) . . ? C26 C30 H11 120.0 . . ? C33 C30 H11 120.0 . . ? C23 C31 C11 122.7(5) . . ? C23 C31 H12 118.7 . . ? C11 C31 H12 118.7 . . ? C41 C32 C15 120.4(4) . . ? C41 C32 C16 130.0(5) . . ? C15 C32 C16 109.7(4) . . ? C13 C33 C30 118.3(5) . . ? C13 C33 H13 120.8 . . ? C30 C33 H13 120.8 . . ? C40 C34 C37 121.5(5) . . ? C40 C34 H14 119.3 . . ? C37 C34 H14 119.3 . . ? C11 C35 H15 109.5 . . ? C11 C35 H16 109.5 . . ? H15 C35 H16 109.5 . . ? C11 C35 H17 109.5 . . ? H15 C35 H17 109.5 . . ? H16 C35 H17 109.5 . . ? C23 C36 H18 109.5 . . ? C23 C36 H19 109.5 . . ? H18 C36 H19 109.5 . . ? C23 C36 H20 109.5 . . ? H18 C36 H20 109.5 . . ? H19 C36 H20 109.5 . . ? C34 C37 C27 119.0(5) . . ? C34 C37 H21 120.5 . . ? C27 C37 H21 120.5 . . ? C9 C38 H22 109.5 . . ? C9 C38 H23 109.5 . . ? H22 C38 H23 109.5 . . ? C9 C38 H24 109.5 . . ? H22 C38 H24 109.5 . . ? H23 C38 H24 109.5 . . ? C7 C39 C26 118.5(5) . . ? C7 C39 H25 120.7 . . ? C26 C39 H25 120.7 . . ? C34 C40 C42 119.9(6) . . ? C34 C40 H26 120.0 . . ? C42 C40 H26 120.0 . . ? C32 C41 C20 117.0(5) . . ? C32 C41 H27 121.5 . . ? C20 C41 H27 121.5 . . ? C5 C42 C40 118.5(5) . . ? C5 C42 H28 120.7 . . ? C40 C42 H28 120.7 . . ? C18 C43 H29 109.5 . . ? C18 C43 H30 109.5 . . ? H29 C43 H30 109.5 . . ? C18 C43 H31 109.5 . . ? H29 C43 H31 109.5 . . ? H30 C43 H31 109.5 . . ? O3 C44 C47 119.6(6) . . ? O3 C44 C46 122.7(6) . . ? C47 C44 C46 117.7(6) . . ? C44 C46 H32 109.5 . . ? C44 C46 H33 109.5 . . ? H32 C46 H33 109.5 . . ? C44 C46 H34 109.5 . . ? H32 C46 H34 109.5 . . ? H33 C46 H34 109.5 . . ? C44 C47 H35 109.5 . . ? C44 C47 H36 109.5 . . ? H35 C47 H36 109.5 . . ? C44 C47 H37 109.5 . . ? H35 C47 H37 109.5 . . ? H36 C47 H37 109.5 . . ? C29 C48 H38 109.5 . . ? C29 C48 H39 109.5 . . ? H38 C48 H39 109.5 . . ? C29 C48 H40 109.5 . . ? H38 C48 H40 109.5 . . ? H39 C48 H40 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C25 O1 O2 C10 -1.9(4) . . . . ? C42 C5 C8 C24 -178.3(5) . . . . ? C27 C5 C8 C24 0.9(6) . . . . ? C42 C5 C8 C17 -2.5(8) . . . . ? C27 C5 C8 C17 176.7(4) . . . . ? O1 O2 C10 C15 -170.8(3) . . . . ? O1 O2 C10 C7 59.5(4) . . . . ? O1 O2 C10 C6 -58.5(4) . . . . ? C13 C7 C10 O2 -60.1(5) . . . . ? C39 C7 C10 O2 118.2(5) . . . . ? C13 C7 C10 C15 178.6(4) . . . . ? C39 C7 C10 C15 -3.2(7) . . . . ? C13 C7 C10 C6 56.9(5) . . . . ? C39 C7 C10 C6 -124.8(5) . . . . ? C16 C6 C10 O2 -118.1(4) . . . . ? C24 C6 C10 O2 59.9(5) . . . . ? C16 C6 C10 C15 -4.0(5) . . . . ? C24 C6 C10 C15 173.9(4) . . . . ? C16 C6 C10 C7 126.8(4) . . . . ? C24 C6 C10 C7 -55.3(5) . . . . ? C21 C9 C12 C19 1.7(8) . . . . ? C38 C9 C12 C19 -176.7(5) . . . . ? C39 C7 C13 C33 0.4(7) . . . . ? C10 C7 C13 C33 178.8(4) . . . . ? C39 C7 C13 C25 -178.0(4) . . . . ? C10 C7 C13 C25 0.4(5) . . . . ? O2 C10 C15 C28 -62.9(6) . . . . ? C7 C10 C15 C28 57.7(7) . . . . ? C6 C10 C15 C28 -178.0(5) . . . . ? O2 C10 C15 C32 118.1(4) . . . . ? C7 C10 C15 C32 -121.3(5) . . . . ? C6 C10 C15 C32 3.0(5) . . . . ? C24 C6 C16 C32 -173.5(6) . . . . ? C10 C6 C16 C32 3.4(5) . . . . ? C24 C6 C16 C3 8.1(10) . . . . ? C10 C6 C16 C3 -175.0(4) . . . . ? C29 C3 C16 C6 -118.7(6) . . . . ? C19 C3 C16 C6 63.9(7) . . . . ? C29 C3 C16 C32 63.1(6) . . . . ? C19 C3 C16 C32 -114.3(5) . . . . ? C31 C11 C17 C18 -0.9(7) . . . . ? C35 C11 C17 C18 -180.0(5) . . . . ? C31 C11 C17 C8 -178.2(5) . . . . ? C35 C11 C17 C8 2.8(7) . . . . ? C24 C8 C17 C11 -113.8(6) . . . . ? C5 C8 C17 C11 71.5(6) . . . . ? C24 C8 C17 C18 69.0(7) . . . . ? C5 C8 C17 C18 -105.8(6) . . . . ? C23 C4 C18 C17 -0.5(7) . . . . ? C23 C4 C18 C43 178.3(5) . . . . ? C11 C17 C18 C4 1.3(7) . . . . ? C8 C17 C18 C4 178.5(4) . . . . ? C11 C17 C18 C43 -177.6(5) . . . . ? C8 C17 C18 C43 -0.3(7) . . . . ? C9 C12 C19 C3 -1.3(8) . . . . ? C9 C12 C19 C22 175.8(5) . . . . ? C29 C3 C19 C12 0.3(7) . . . . ? C16 C3 C19 C12 177.8(5) . . . . ? C29 C3 C19 C22 -176.7(5) . . . . ? C16 C3 C19 C22 0.8(7) . . . . ? C28 C14 C20 C41 1.0(7) . . . . ? C12 C9 C21 C29 -1.2(8) . . . . ? C38 C9 C21 C29 177.2(5) . . . . ? C18 C4 C23 C31 -0.5(7) . . . . ? C18 C4 C23 C36 179.8(5) . . . . ? C17 C8 C24 C6 -2.1(10) . . . . ? C5 C8 C24 C6 173.3(6) . . . . ? C17 C8 C24 C25 -178.7(5) . . . . ? C5 C8 C24 C25 -3.3(5) . . . . ? C16 C6 C24 C8 -0.4(11) . . . . ? C10 C6 C24 C8 -177.3(6) . . . . ? C16 C6 C24 C25 176.2(6) . . . . ? C10 C6 C24 C25 -0.7(5) . . . . ? O2 O1 C25 C27 171.4(3) . . . . ? O2 O1 C25 C13 -57.8(4) . . . . ? O2 O1 C25 C24 60.2(4) . . . . ? C7 C13 C25 O1 60.1(5) . . . . ? C33 C13 C25 O1 -118.1(5) . . . . ? C7 C13 C25 C27 -177.0(4) . . . . ? C33 C13 C25 C27 4.8(7) . . . . ? C7 C13 C25 C24 -57.0(5) . . . . ? C33 C13 C25 C24 124.8(5) . . . . ? C8 C24 C25 O1 117.7(4) . . . . ? C6 C24 C25 O1 -60.0(5) . . . . ? C8 C24 C25 C27 4.5(5) . . . . ? C6 C24 C25 C27 -173.2(4) . . . . ? C8 C24 C25 C13 -125.3(5) . . . . ? C6 C24 C25 C13 57.1(5) . . . . ? C42 C5 C27 C37 1.8(8) . . . . ? C8 C5 C27 C37 -177.5(4) . . . . ? C42 C5 C27 C25 -178.7(5) . . . . ? C8 C5 C27 C25 2.0(6) . . . . ? O1 C25 C27 C37 61.7(7) . . . . ? C13 C25 C27 C37 -61.6(7) . . . . ? C24 C25 C27 C37 175.7(5) . . . . ? O1 C25 C27 C5 -117.8(4) . . . . ? C13 C25 C27 C5 118.9(5) . . . . ? C24 C25 C27 C5 -3.8(5) . . . . ? C32 C15 C28 C14 -0.8(7) . . . . ? C10 C15 C28 C14 -179.8(4) . . . . ? C20 C14 C28 C15 0.5(7) . . . . ? C9 C21 C29 C3 0.3(8) . . . . ? C9 C21 C29 C48 -179.9(5) . . . . ? C19 C3 C29 C21 0.1(7) . . . . ? C16 C3 C29 C21 -177.3(5) . . . . ? C19 C3 C29 C48 -179.6(5) . . . . ? C16 C3 C29 C48 2.9(7) . . . . ? C39 C26 C30 C33 -0.4(7) . . . . ? C4 C23 C31 C11 0.9(8) . . . . ? C36 C23 C31 C11 -179.4(5) . . . . ? C17 C11 C31 C23 -0.2(8) . . . . ? C35 C11 C31 C23 178.9(5) . . . . ? C28 C15 C32 C41 -0.3(7) . . . . ? C10 C15 C32 C41 178.8(4) . . . . ? C28 C15 C32 C16 179.8(4) . . . . ? C10 C15 C32 C16 -1.1(5) . . . . ? C6 C16 C32 C41 178.6(5) . . . . ? C3 C16 C32 C41 -2.8(8) . . . . ? C6 C16 C32 C15 -1.6(5) . . . . ? C3 C16 C32 C15 177.0(4) . . . . ? C7 C13 C33 C30 0.3(7) . . . . ? C25 C13 C33 C30 178.4(4) . . . . ? C26 C30 C33 C13 -0.3(7) . . . . ? C40 C34 C37 C27 1.1(9) . . . . ? C5 C27 C37 C34 -1.4(8) . . . . ? C25 C27 C37 C34 179.2(5) . . . . ? C13 C7 C39 C26 -1.1(7) . . . . ? C10 C7 C39 C26 -179.2(4) . . . . ? C30 C26 C39 C7 1.1(7) . . . . ? C37 C34 C40 C42 -1.3(9) . . . . ? C15 C32 C41 C20 1.8(7) . . . . ? C16 C32 C41 C20 -178.4(5) . . . . ? C14 C20 C41 C32 -2.2(7) . . . . ? C27 C5 C42 C40 -1.9(8) . . . . ? C8 C5 C42 C40 177.3(5) . . . . ? C34 C40 C42 C5 1.7(8) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.38 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.361 _refine_diff_density_min -0.447 _refine_diff_density_rms 0.087 _database_code_depnum_ccdc_archive 'CCDC 960647' ####################################################################### # # 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_4plus2_Dimer #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C90 H73 Cl' _chemical_formula_moiety 'C84 H68, C6 H5 Cl' _chemical_formula_weight 1190.02 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z #------------------------------------------------------------------------------ _cell_length_a 8.50440(10) _cell_length_b 19.2480(2) _cell_length_c 20.4545(3) _cell_angle_alpha 82.0704(8) _cell_angle_beta 78.1032(5) _cell_angle_gamma 82.3308(7) _cell_volume 3225.90(7) _cell_formula_units_Z 2 _cell_measurement_reflns_used 27765 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_measurement_temperature 296 #------------------------------------------------------------------------------ _exptl_crystal_description plate _exptl_crystal_colour purple _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _exptl_crystal_density_diffrn 1.225 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1260.00 _exptl_absorpt_coefficient_mu 0.000 _exptl_absorpt_correction_type none #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 296 _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.80000 _diffrn_measurement_device_type 'CCD (Q315 ADSC)' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 27765 _diffrn_reflns_av_R_equivalents 0.035 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_max 0.858 _diffrn_measured_fraction_theta_full 0.858 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 8921 _reflns_number_gt 8380 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0673 _refine_ls_wR_factor_ref 0.1817 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 8921 _refine_ls_number_parameters 832 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1014P)^2^+2.0867P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 1.39 _refine_diff_density_min -0.51 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; Cl Cl 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.6009(6) 0.6178(3) 0.4121(3) 0.363(3) Uani 1 2 d . . . C1 C 0.4206(2) 0.16732(11) 0.05581(10) 0.0305(5) Uani 1 2 d . . . C2 C 0.3259(2) 0.11436(11) 0.05479(11) 0.0326(5) Uani 1 2 d . . . C3 C 0.2285(2) 0.08653(12) 0.11311(11) 0.0334(5) Uani 1 2 d . . . C4 C 0.2278(2) 0.11045(12) 0.17410(10) 0.0331(5) Uani 1 2 d . . . C5 C 0.3246(2) 0.16216(11) 0.17576(10) 0.0295(4) Uani 1 2 d . . . C6 C 0.3487(2) 0.19413(11) 0.23380(10) 0.0294(5) Uani 1 2 d . . . C7 C 0.4527(2) 0.24519(11) 0.21050(10) 0.0290(4) Uani 1 2 d . . . C8 C 0.5239(2) 0.29201(11) 0.24292(10) 0.0301(5) Uani 1 2 d . . . C9 C 0.5389(2) 0.29439(11) 0.30874(10) 0.0323(5) Uani 1 2 d . . . C10 C 0.6209(2) 0.35583(12) 0.31076(11) 0.0342(5) Uani 1 2 d . . . C11 C 0.6710(3) 0.37781(13) 0.36443(12) 0.0395(5) Uani 1 2 d . . . C12 C 0.7588(3) 0.43568(14) 0.35282(13) 0.0451(6) Uani 1 2 d . . . C13 C 0.7976(3) 0.47026(14) 0.28871(13) 0.0468(6) Uani 1 2 d . . . C14 C 0.7491(3) 0.44843(13) 0.23421(12) 0.0415(5) Uani 1 2 d . . . C15 C 0.6577(2) 0.39148(12) 0.24527(11) 0.0343(5) Uani 1 2 d . . . C16 C 0.5988(2) 0.35118(11) 0.20074(10) 0.0310(5) Uani 1 2 d . . . C17 C 0.6117(2) 0.35976(11) 0.13228(10) 0.0307(5) Uani 1 2 d . . . C18 C 0.6465(2) 0.42574(12) 0.09066(11) 0.0342(5) Uani 1 2 d . . . C19 C 0.6525(2) 0.43464(11) 0.02443(11) 0.0341(5) Uani 1 2 d . . . C20 C 0.6476(2) 0.37801(11) -0.01706(10) 0.0306(5) Uani 1 2 d . . . C21 C 0.6311(2) 0.30434(11) 0.02415(10) 0.0285(4) Uani 1 2 d . . . C22 C 0.5736(2) 0.30377(11) 0.09898(10) 0.0277(4) Uani 1 2 d . . . C23 C 0.4939(2) 0.24952(11) 0.13655(10) 0.0279(4) Uani 1 2 d . . . C24 C 0.4194(2) 0.19299(11) 0.11648(10) 0.0284(4) Uani 1 2 d . . . C25 C 0.2550(2) 0.17365(12) 0.30194(10) 0.0316(5) Uani 1 2 d . . . C26 C 0.2849(3) 0.10670(12) 0.33643(11) 0.0345(5) Uani 1 2 d . . . C27 C 0.1871(3) 0.08884(13) 0.39842(11) 0.0406(5) Uani 1 2 d . . . C28 C 0.0607(3) 0.13499(14) 0.42716(11) 0.0419(6) Uani 1 2 d . . . C29 C 0.0296(3) 0.20004(14) 0.39117(11) 0.0406(5) Uani 1 2 d . . . C30 C 0.1234(3) 0.22042(12) 0.32913(11) 0.0353(5) Uani 1 2 d . . . C31 C 0.4210(3) 0.05354(12) 0.30848(11) 0.0393(5) Uani 1 2 d . . . C32 C -0.0392(3) 0.11587(18) 0.49570(13) 0.0575(7) Uani 1 2 d . . . C33 C 0.0823(3) 0.29023(13) 0.29041(12) 0.0436(6) Uani 1 2 d . . . C34 C 0.5060(3) 0.24131(12) 0.36829(10) 0.0343(5) Uani 1 2 d . . . C35 C 0.6052(3) 0.17699(13) 0.37018(11) 0.0384(5) Uani 1 2 d . . . C36 C 0.5782(3) 0.12835(14) 0.42688(12) 0.0451(6) Uani 1 2 d . . . C37 C 0.4560(3) 0.14142(14) 0.48200(12) 0.0474(6) Uani 1 2 d . . . C38 C 0.3644(3) 0.20607(14) 0.48008(11) 0.0451(6) Uani 1 2 d . . . C39 C 0.3871(3) 0.25718(13) 0.42472(11) 0.0388(5) Uani 1 2 d . . . C40 C 0.7375(3) 0.16053(13) 0.31106(12) 0.0448(6) Uani 1 2 d . . . C41 C 0.4202(4) 0.08510(17) 0.54003(14) 0.0620(8) Uani 1 2 d . . . C42 C 0.2830(3) 0.32660(14) 0.42537(12) 0.0461(6) Uani 1 2 d . . . C43 C 0.8063(3) 0.50635(12) -0.13036(11) 0.0364(5) Uani 1 2 d . . . C44 C 0.7812(3) 0.55155(13) -0.18745(12) 0.0407(5) Uani 1 2 d . . . C45 C 0.7492(3) 0.52560(13) -0.24264(12) 0.0430(6) Uani 1 2 d . . . C46 C 0.7446(3) 0.45378(13) -0.24321(12) 0.0401(5) Uani 1 2 d . . . C47 C 0.7712(2) 0.40835(12) -0.18628(11) 0.0340(5) Uani 1 2 d . . . C48 C 0.7720(2) 0.33140(11) -0.17362(10) 0.0313(5) Uani 1 2 d . . . C49 C 0.8002(2) 0.31049(11) -0.11055(10) 0.0286(4) Uani 1 2 d . . . C50 C 0.8109(2) 0.24458(11) -0.06675(10) 0.0283(4) Uani 1 2 d . . . C51 C 0.8310(2) 0.17476(11) -0.07315(10) 0.0285(4) Uani 1 2 d . . . C52 C 0.8255(2) 0.13549(11) -0.00600(10) 0.0291(4) Uani 1 2 d . . . C53 C 0.8321(2) 0.06306(11) 0.01348(11) 0.0330(5) Uani 1 2 d . . . C54 C 0.8226(3) 0.03881(12) 0.08112(11) 0.0359(5) Uani 1 2 d . . . C55 C 0.8117(2) 0.08549(12) 0.12844(11) 0.0339(5) Uani 1 2 d . . . C56 C 0.8068(2) 0.15795(11) 0.10933(10) 0.0309(5) Uani 1 2 d . . . C57 C 0.8097(2) 0.18299(11) 0.04217(10) 0.0284(4) Uani 1 2 d . . . C58 C 0.8002(2) 0.25701(11) 0.00655(10) 0.0283(4) Uani 1 2 d . . . C59 C 0.9378(2) 0.29948(11) 0.00833(10) 0.0296(5) Uani 1 2 d . . . C60 C 1.0531(2) 0.28227(11) 0.04838(11) 0.0337(5) Uani 1 2 d . . . C61 C 1.1751(3) 0.32547(12) 0.04196(12) 0.0393(5) Uani 1 2 d . . . C62 C 1.1846(3) 0.38424(12) -0.00515(12) 0.0389(5) Uani 1 2 d . . . C63 C 1.0693(2) 0.40233(11) -0.04522(11) 0.0341(5) Uani 1 2 d . . . C64 C 0.9456(2) 0.36069(11) -0.03805(10) 0.0302(5) Uani 1 2 d . . . C65 C 0.8062(2) 0.37382(11) -0.07473(10) 0.0298(5) Uani 1 2 d . . . C66 C 0.7990(2) 0.43469(11) -0.12943(10) 0.0320(5) Uani 1 2 d . . . C67 C 0.7300(3) 0.29070(11) -0.22249(10) 0.0332(5) Uani 1 2 d . . . C68 C 0.8460(3) 0.26668(12) -0.27672(10) 0.0364(5) Uani 1 2 d . . . C69 C 0.7988(3) 0.22860(14) -0.32043(11) 0.0443(6) Uani 1 2 d . . . C70 C 0.6395(3) 0.21466(14) -0.31367(12) 0.0451(6) Uani 1 2 d . . . C71 C 0.5255(3) 0.24254(14) -0.26246(12) 0.0437(6) Uani 1 2 d . . . C72 C 0.5673(3) 0.28020(12) -0.21658(11) 0.0375(5) Uani 1 2 d . . . C73 C 1.0179(3) 0.28438(14) -0.28824(12) 0.0444(6) Uani 1 2 d . . . C74 C 0.5908(4) 0.17079(18) -0.35959(14) 0.0620(8) Uani 1 2 d . . . C75 C 0.4394(3) 0.31031(15) -0.16195(13) 0.0475(6) Uani 1 2 d . . . C76 C 0.8757(2) 0.13891(11) -0.13560(10) 0.0296(5) Uani 1 2 d . . . C77 C 1.0381(3) 0.13529(12) -0.16849(10) 0.0336(5) Uani 1 2 d . . . C78 C 1.0846(3) 0.10055(12) -0.22604(11) 0.0374(5) Uani 1 2 d . . . C79 C 0.9756(3) 0.06987(12) -0.25146(11) 0.0397(5) Uani 1 2 d . . . C80 C 0.8164(3) 0.07251(12) -0.21693(11) 0.0372(5) Uani 1 2 d . . . C81 C 0.7647(3) 0.10599(11) -0.15883(10) 0.0324(5) Uani 1 2 d . . . C82 C 1.1606(3) 0.16713(13) -0.14134(12) 0.0402(5) Uani 1 2 d . . . C83 C 1.0262(4) 0.03557(15) -0.31561(12) 0.0520(7) Uani 1 2 d . . . C84 C 0.5921(3) 0.10505(13) -0.12137(12) 0.0384(5) Uani 1 2 d . . . C85 C 0.4203(4) 0.60576(17) 0.42918(15) 0.0588(7) Uani 1 2 d . . . C86 C 0.3679(4) 0.54608(19) 0.41595(17) 0.0708(9) Uani 1 2 d . . . C87 C 0.2060(4) 0.53584(19) 0.42963(15) 0.0669(8) Uani 1 2 d . . . C88 C 0.0944(4) 0.5878(2) 0.45771(16) 0.0723(9) Uani 1 2 d . . . C89 C 0.1454(5) 0.64766(19) 0.47172(19) 0.0791(11) Uani 1 2 d . . . C90 C 0.3076(4) 0.65639(17) 0.45736(14) 0.0654(8) Uani 1 2 d . . . H1 H 0.48452 0.18564 0.01629 0.0366 Uiso 1 2 calc R . . H2 H 0.3276 0.09712 0.01433 0.0391 Uiso 1 2 calc R . . H3 H 0.1637 0.05183 0.11123 0.0401 Uiso 1 2 calc R . . H4 H 0.16303 0.09195 0.21333 0.0397 Uiso 1 2 calc R . . H11 H 0.64614 0.35412 0.40744 0.0473 Uiso 1 2 calc R . . H12 H 0.79172 0.45125 0.38842 0.0541 Uiso 1 2 calc R . . H13 H 0.85706 0.50872 0.2817 0.0562 Uiso 1 2 calc R . . H14 H 0.77733 0.4716 0.19116 0.0498 Uiso 1 2 calc R . . H18 H 0.66538 0.46323 0.11118 0.0411 Uiso 1 2 calc R . . H19 H 0.66039 0.48007 0.00252 0.0410 Uiso 1 2 calc R . . H20 H 0.55369 0.3905 -0.03886 0.0367 Uiso 1 2 calc R . . H21 H 0.55156 0.2827 0.00733 0.0342 Uiso 1 2 calc R . . H27 H 0.20732 0.04437 0.42132 0.0488 Uiso 1 2 calc R . . H29 H -0.05689 0.23108 0.40912 0.0487 Uiso 1 2 calc R . . H31A H 0.37985 0.00928 0.30929 0.0471 Uiso 1 2 calc R . . H31B H 0.50301 0.04722 0.33538 0.0471 Uiso 1 2 calc R . . H31C H 0.46648 0.07035 0.263 0.0471 Uiso 1 2 calc R . . H32A H -0.15176 0.1277 0.49421 0.0690 Uiso 1 2 calc R . . H32B H -0.01076 0.14159 0.5278 0.0690 Uiso 1 2 calc R . . H32C H -0.0186 0.06616 0.50873 0.0690 Uiso 1 2 calc R . . H33A H 0.16873 0.31904 0.28562 0.0523 Uiso 1 2 calc R . . H33B H -0.01553 0.31348 0.31411 0.0523 Uiso 1 2 calc R . . H33C H 0.06737 0.28284 0.24672 0.0523 Uiso 1 2 calc R . . H36 H 0.64372 0.08565 0.42815 0.0541 Uiso 1 2 calc R . . H38 H 0.28446 0.21596 0.5171 0.0541 Uiso 1 2 calc R . . H40A H 0.69027 0.15133 0.27477 0.0537 Uiso 1 2 calc R . . H40B H 0.80707 0.11973 0.3241 0.0537 Uiso 1 2 calc R . . H40C H 0.79914 0.20005 0.29671 0.0537 Uiso 1 2 calc R . . H41A H 0.35618 0.05277 0.5286 0.0744 Uiso 1 2 calc R . . H41B H 0.3618 0.10648 0.57892 0.0744 Uiso 1 2 calc R . . H41C H 0.51982 0.06008 0.54964 0.0744 Uiso 1 2 calc R . . H42A H 0.3499 0.3643 0.41023 0.0553 Uiso 1 2 calc R . . H42B H 0.22505 0.33169 0.47028 0.0553 Uiso 1 2 calc R . . H42C H 0.20757 0.32821 0.39602 0.0553 Uiso 1 2 calc R . . H43 H 0.82776 0.52398 -0.09338 0.0436 Uiso 1 2 calc R . . H44 H 0.78606 0.59969 -0.18852 0.0488 Uiso 1 2 calc R . . H45 H 0.73034 0.55672 -0.27993 0.0516 Uiso 1 2 calc R . . H46 H 0.72446 0.43645 -0.28058 0.0481 Uiso 1 2 calc R . . H53 H 0.84267 0.0316 -0.01822 0.0396 Uiso 1 2 calc R . . H54 H 0.82346 -0.00931 0.09501 0.0430 Uiso 1 2 calc R . . H55 H 0.80768 0.06811 0.17343 0.0407 Uiso 1 2 calc R . . H56 H 0.80159 0.18896 0.14097 0.0371 Uiso 1 2 calc R . . H60 H 1.04903 0.24207 0.07939 0.0405 Uiso 1 2 calc R . . H61 H 1.25117 0.31471 0.06966 0.0472 Uiso 1 2 calc R . . H62 H 1.26897 0.41185 -0.00999 0.0466 Uiso 1 2 calc R . . H63 H 1.07531 0.44216 -0.07667 0.0409 Uiso 1 2 calc R . . H69 H 0.87592 0.2117 -0.35553 0.0532 Uiso 1 2 calc R . . H71 H 0.4176 0.2358 -0.25874 0.0524 Uiso 1 2 calc R . . H73A H 1.02458 0.33114 -0.31133 0.0533 Uiso 1 2 calc R . . H73B H 1.0877 0.25117 -0.31498 0.0533 Uiso 1 2 calc R . . H73C H 1.05069 0.28209 -0.24575 0.0533 Uiso 1 2 calc R . . H74A H 0.65422 0.12562 -0.3584 0.0744 Uiso 1 2 calc R . . H74B H 0.60867 0.1942 -0.40466 0.0744 Uiso 1 2 calc R . . H74C H 0.47838 0.16441 -0.34519 0.0744 Uiso 1 2 calc R . . H75A H 0.4519 0.28503 -0.11915 0.0570 Uiso 1 2 calc R . . H75B H 0.33432 0.30582 -0.17017 0.0570 Uiso 1 2 calc R . . H75C H 0.45073 0.35925 -0.16179 0.0570 Uiso 1 2 calc R . . H78 H 1.19213 0.09795 -0.24796 0.0449 Uiso 1 2 calc R . . H80 H 0.74225 0.05131 -0.23308 0.0447 Uiso 1 2 calc R . . H82A H 1.13293 0.21726 -0.14284 0.0483 Uiso 1 2 calc R . . H82B H 1.26594 0.15724 -0.16819 0.0483 Uiso 1 2 calc R . . H82C H 1.16078 0.14716 -0.09567 0.0483 Uiso 1 2 calc R . . H83A H 1.00124 0.06861 -0.35267 0.0624 Uiso 1 2 calc R . . H83B H 0.96928 -0.00503 -0.31208 0.0624 Uiso 1 2 calc R . . H83C H 1.14045 0.02129 -0.32293 0.0624 Uiso 1 2 calc R . . H84A H 0.59068 0.07978 -0.07741 0.0461 Uiso 1 2 calc R . . H84B H 0.53251 0.08218 -0.14568 0.0461 Uiso 1 2 calc R . . H84C H 0.54343 0.15258 -0.11721 0.0461 Uiso 1 2 calc R . . H86 H 0.44346 0.51123 0.39716 0.0849 Uiso 1 2 calc R . . H87 H 0.1728 0.49483 0.42014 0.0803 Uiso 1 2 calc R . . H88 H -0.01515 0.58212 0.46706 0.0868 Uiso 1 2 calc R . . H89 H 0.07047 0.68246 0.49096 0.0950 Uiso 1 2 calc R . . H90 H 0.34114 0.69728 0.46694 0.0785 Uiso 1 2 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl1 0.236(4) 0.392(7) 0.480(7) -0.000(4) -0.088(4) -0.119(6) C1 0.0265(10) 0.0309(11) 0.0317(10) 0.0012(8) -0.0047(8) -0.0007(8) C2 0.0294(10) 0.0336(12) 0.0349(11) 0.0009(9) -0.0081(8) -0.0055(9) C3 0.0289(10) 0.0318(12) 0.0400(11) -0.0035(8) -0.0085(8) -0.0026(9) C4 0.0278(10) 0.0335(12) 0.0350(11) -0.0017(9) -0.0033(8) 0.0003(9) C5 0.0252(9) 0.0279(11) 0.0335(10) 0.0023(8) -0.0067(8) -0.0005(8) C6 0.0257(10) 0.0285(11) 0.0316(10) 0.0036(8) -0.0057(8) -0.0007(8) C7 0.0234(9) 0.0290(11) 0.0324(10) 0.0032(8) -0.0057(8) -0.0013(8) C8 0.0250(9) 0.0288(11) 0.0343(11) 0.0038(8) -0.0045(8) -0.0043(8) C9 0.0275(10) 0.0321(12) 0.0360(11) 0.0044(8) -0.0063(8) -0.0068(9) C10 0.0271(10) 0.0340(12) 0.0408(11) 0.0045(9) -0.0057(8) -0.0106(9) C11 0.0360(11) 0.0403(14) 0.0431(12) 0.0025(10) -0.0080(9) -0.0139(10) C12 0.0381(12) 0.0471(15) 0.0546(14) 0.0002(11) -0.0108(10) -0.0230(11) C13 0.0404(13) 0.0423(15) 0.0612(15) -0.0069(11) -0.0076(11) -0.0184(12) C14 0.0371(12) 0.0382(14) 0.0494(13) -0.0050(10) -0.0041(10) -0.0104(10) C15 0.0274(10) 0.0334(12) 0.0414(12) 0.0024(9) -0.0049(8) -0.0096(9) C16 0.0252(10) 0.0289(11) 0.0377(11) 0.0018(8) -0.0049(8) -0.0054(9) C17 0.0218(9) 0.0290(11) 0.0387(11) 0.0021(8) -0.0027(8) -0.0037(9) C18 0.0306(10) 0.0277(12) 0.0425(12) -0.0016(8) -0.0016(9) -0.0070(9) C19 0.0304(10) 0.0253(11) 0.0410(12) 0.0007(8) 0.0009(9) 0.0011(9) C20 0.0238(10) 0.0299(12) 0.0345(11) 0.0024(8) -0.0038(8) 0.0009(8) C21 0.0229(9) 0.0282(11) 0.0327(10) -0.0005(8) -0.0049(8) -0.0008(8) C22 0.0199(9) 0.0273(11) 0.0347(10) 0.0031(8) -0.0068(8) -0.0024(8) C23 0.0224(9) 0.0268(11) 0.0326(10) 0.0030(8) -0.0056(8) -0.0025(8) C24 0.0228(9) 0.0270(11) 0.0332(10) 0.0029(8) -0.0063(8) -0.0000(8) C25 0.0300(10) 0.0339(12) 0.0316(10) -0.0048(9) -0.0080(8) -0.0022(9) C26 0.0369(11) 0.0347(13) 0.0340(11) -0.0064(9) -0.0121(9) -0.0001(9) C27 0.0476(13) 0.0417(14) 0.0345(11) -0.0130(10) -0.0136(10) 0.0056(10) C28 0.0406(12) 0.0542(16) 0.0322(11) -0.0155(11) -0.0061(9) -0.0000(10) C29 0.0331(11) 0.0501(15) 0.0375(12) -0.0041(10) -0.0030(9) -0.0073(10) C30 0.0310(11) 0.0386(13) 0.0355(11) -0.0036(9) -0.0050(9) -0.0038(9) C31 0.0462(13) 0.0314(12) 0.0414(12) -0.0012(10) -0.0148(10) -0.0012(9) C32 0.0552(15) 0.078(2) 0.0369(13) -0.0186(14) -0.0024(11) 0.0039(13) C33 0.0356(12) 0.0402(14) 0.0476(13) 0.0050(10) 0.0009(10) -0.0019(10) C34 0.0357(11) 0.0361(13) 0.0344(11) -0.0035(9) -0.0126(9) -0.0063(9) C35 0.0406(12) 0.0381(13) 0.0402(12) -0.0001(10) -0.0182(10) -0.0057(10) C36 0.0563(14) 0.0379(14) 0.0472(13) -0.0024(11) -0.0269(12) -0.0027(10) C37 0.0624(16) 0.0486(16) 0.0376(12) -0.0147(12) -0.0229(11) 0.0012(11) C38 0.0514(14) 0.0543(16) 0.0321(11) -0.0142(12) -0.0083(10) -0.0050(10) C39 0.0401(12) 0.0445(14) 0.0338(11) -0.0054(10) -0.0093(9) -0.0068(10) C40 0.0430(13) 0.0405(14) 0.0513(14) 0.0087(11) -0.0164(11) -0.0088(11) C41 0.093(2) 0.0569(18) 0.0446(14) -0.0270(16) -0.0279(14) 0.0060(12) C42 0.0450(13) 0.0493(15) 0.0404(12) 0.0007(11) -0.0007(10) -0.0099(11) C43 0.0325(11) 0.0335(13) 0.0395(12) -0.0023(9) -0.0015(9) -0.0010(9) C44 0.0387(12) 0.0301(12) 0.0476(13) -0.0010(9) -0.0016(10) 0.0026(10) C45 0.0412(12) 0.0382(14) 0.0433(12) 0.0006(10) -0.0063(10) 0.0096(10) C46 0.0384(12) 0.0399(14) 0.0397(12) -0.0023(10) -0.0088(9) 0.0032(10) C47 0.0276(10) 0.0339(12) 0.0369(11) -0.0007(8) -0.0034(8) 0.0014(9) C48 0.0254(10) 0.0324(12) 0.0335(11) 0.0000(8) -0.0037(8) -0.0001(9) C49 0.0207(9) 0.0286(11) 0.0349(11) -0.0008(8) -0.0034(8) -0.0024(8) C50 0.0207(9) 0.0315(12) 0.0312(10) -0.0008(8) -0.0040(7) -0.0018(8) C51 0.0210(9) 0.0300(11) 0.0333(10) -0.0003(8) -0.0043(8) -0.0034(8) C52 0.0206(9) 0.0307(11) 0.0344(10) 0.0015(8) -0.0052(8) -0.0021(8) C53 0.0287(10) 0.0297(12) 0.0386(11) 0.0016(8) -0.0050(8) -0.0041(9) C54 0.0324(11) 0.0286(12) 0.0426(12) 0.0014(9) -0.0053(9) 0.0023(9) C55 0.0281(10) 0.0356(12) 0.0343(11) 0.0027(9) -0.0052(8) 0.0019(9) C56 0.0233(9) 0.0336(12) 0.0337(10) 0.0030(8) -0.0052(8) -0.0024(9) C57 0.0197(9) 0.0291(11) 0.0345(10) 0.0014(8) -0.0047(8) -0.0018(8) C58 0.0240(9) 0.0277(11) 0.0312(10) 0.0010(8) -0.0040(8) -0.0026(8) C59 0.0239(10) 0.0280(11) 0.0347(10) 0.0020(8) -0.0020(8) -0.0062(8) C60 0.0293(10) 0.0284(11) 0.0423(12) 0.0045(8) -0.0084(9) -0.0048(9) C61 0.0275(10) 0.0360(13) 0.0566(14) 0.0034(9) -0.0146(10) -0.0097(10) C62 0.0251(10) 0.0340(13) 0.0576(14) -0.0010(9) -0.0063(9) -0.0100(10) C63 0.0275(10) 0.0296(12) 0.0425(12) -0.0013(9) -0.0010(9) -0.0053(9) C64 0.0254(10) 0.0293(11) 0.0332(10) 0.0028(8) -0.0018(8) -0.0056(8) C65 0.0248(10) 0.0287(12) 0.0334(10) -0.0017(8) -0.0026(8) -0.0008(8) C66 0.0251(10) 0.0311(12) 0.0362(11) 0.0002(8) -0.0023(8) 0.0006(9) C67 0.0351(11) 0.0306(12) 0.0324(10) -0.0002(9) -0.0094(9) 0.0029(9) C68 0.0377(11) 0.0361(13) 0.0326(11) 0.0008(9) -0.0070(9) 0.0017(9) C69 0.0493(14) 0.0479(15) 0.0332(11) 0.0005(11) -0.0070(10) -0.0027(10) C70 0.0543(14) 0.0461(15) 0.0371(12) -0.0086(11) -0.0138(10) -0.0023(10) C71 0.0410(12) 0.0487(15) 0.0429(13) -0.0086(11) -0.0123(10) -0.0003(11) C72 0.0358(11) 0.0374(13) 0.0391(12) -0.0036(9) -0.0097(9) -0.0002(9) C73 0.0378(12) 0.0496(15) 0.0412(12) 0.0008(10) -0.0031(10) -0.0008(10) C74 0.0753(19) 0.069(2) 0.0483(15) -0.0195(16) -0.0164(13) -0.0121(13) C75 0.0345(12) 0.0519(16) 0.0567(15) -0.0067(11) -0.0052(10) -0.0118(12) C76 0.0285(10) 0.0269(11) 0.0306(10) 0.0031(8) -0.0056(8) 0.0005(8) C77 0.0299(10) 0.0324(12) 0.0343(11) 0.0029(9) -0.0044(8) 0.0022(9) C78 0.0354(11) 0.0359(13) 0.0342(11) 0.0036(9) 0.0010(9) 0.0005(9) C79 0.0498(13) 0.0328(13) 0.0314(11) 0.0031(10) -0.0022(9) -0.0011(9) C80 0.0435(12) 0.0326(12) 0.0362(11) -0.0042(10) -0.0106(9) -0.0014(9) C81 0.0328(11) 0.0289(12) 0.0337(11) -0.0003(9) -0.0070(8) -0.0000(8) C82 0.0277(11) 0.0451(14) 0.0453(12) -0.0008(9) -0.0038(9) -0.0036(10) C83 0.0674(17) 0.0480(16) 0.0369(13) -0.0032(13) -0.0010(11) -0.0084(11) C84 0.0314(11) 0.0404(13) 0.0442(12) -0.0045(9) -0.0078(9) -0.0065(10) C85 0.0567(16) 0.063(2) 0.0586(16) 0.0047(14) -0.0204(13) -0.0095(14) C86 0.0586(18) 0.074(2) 0.082(2) 0.0167(16) -0.0183(15) -0.0306(17) C87 0.0654(19) 0.072(2) 0.0619(18) 0.0010(16) -0.0087(14) -0.0175(15) C88 0.0603(18) 0.078(2) 0.0672(19) -0.0013(16) 0.0089(15) -0.0051(17) C89 0.080(2) 0.056(2) 0.084(2) 0.0042(17) 0.0197(18) -0.0091(17) C90 0.083(2) 0.0542(18) 0.0510(16) 0.0001(15) -0.0018(14) -0.0004(13) #============================================================================== _computing_data_collection Unknown _computing_cell_refinement HKL2000 _computing_data_reduction HKL2000 _computing_structure_solution 'SIR2004 (Burla, et al., 2005)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2011)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Cl1 C85 1.545(6) yes . . C1 C2 1.385(3) yes . . C1 C24 1.395(3) yes . . C2 C3 1.390(3) yes . . C3 C4 1.387(3) yes . . C4 C5 1.382(3) yes . . C5 C6 1.472(3) yes . . C5 C24 1.414(3) yes . . C6 C7 1.380(3) yes . . C6 C25 1.486(3) yes . . C7 C8 1.448(3) yes . . C7 C23 1.474(3) yes . . C8 C9 1.386(3) yes . . C8 C16 1.464(3) yes . . C9 C10 1.460(3) yes . . C9 C34 1.483(3) yes . . C10 C11 1.391(4) yes . . C10 C15 1.412(3) yes . . C11 C12 1.390(4) yes . . C12 C13 1.382(3) yes . . C13 C14 1.398(4) yes . . C14 C15 1.394(3) yes . . C15 C16 1.473(3) yes . . C16 C17 1.370(3) yes . . C17 C18 1.457(3) yes . . C17 C22 1.455(3) yes . . C18 C19 1.333(3) yes . . C19 C20 1.481(3) yes . . C20 C21 1.554(3) yes . . C20 C65 1.599(3) yes . . C21 C22 1.507(3) yes . . C21 C58 1.598(3) yes . . C22 C23 1.376(3) yes . . C23 C24 1.472(3) yes . . C25 C26 1.400(3) yes . . C25 C30 1.409(3) yes . . C26 C27 1.393(3) yes . . C26 C31 1.512(3) yes . . C27 C28 1.385(3) yes . . C28 C29 1.385(3) yes . . C28 C32 1.508(3) yes . . C29 C30 1.389(3) yes . . C30 C33 1.500(3) yes . . C34 C35 1.403(3) yes . . C34 C39 1.408(3) yes . . C35 C36 1.386(3) yes . . C35 C40 1.509(3) yes . . C36 C37 1.393(3) yes . . C37 C38 1.377(4) yes . . C37 C41 1.504(4) yes . . C38 C39 1.393(3) yes . . C39 C42 1.501(3) yes . . C43 C44 1.393(3) yes . . C43 C66 1.386(3) yes . . C44 C45 1.385(4) yes . . C45 C46 1.390(4) yes . . C46 C47 1.395(3) yes . . C47 C48 1.467(3) yes . . C47 C66 1.405(3) yes . . C48 C49 1.357(3) yes . . C48 C67 1.476(3) yes . . C49 C50 1.452(3) yes . . C49 C65 1.518(3) yes . . C50 C51 1.353(3) yes . . C50 C58 1.533(3) yes . . C51 C52 1.469(3) yes . . C51 C76 1.492(3) yes . . C52 C53 1.393(3) yes . . C52 C57 1.409(3) yes . . C53 C54 1.387(3) yes . . C54 C55 1.391(3) yes . . C55 C56 1.393(3) yes . . C56 C57 1.388(3) yes . . C57 C58 1.508(3) yes . . C58 C59 1.523(3) yes . . C59 C60 1.383(3) yes . . C59 C64 1.407(3) yes . . C60 C61 1.389(3) yes . . C61 C62 1.381(3) yes . . C62 C63 1.384(3) yes . . C63 C64 1.379(3) yes . . C64 C65 1.505(3) yes . . C65 C66 1.509(3) yes . . C67 C68 1.410(3) yes . . C67 C72 1.403(3) yes . . C68 C69 1.380(4) yes . . C68 C73 1.509(3) yes . . C69 C70 1.391(4) yes . . C70 C71 1.387(3) yes . . C70 C74 1.496(5) yes . . C71 C72 1.388(4) yes . . C72 C75 1.509(3) yes . . C76 C77 1.403(3) yes . . C76 C81 1.395(3) yes . . C77 C78 1.394(3) yes . . C77 C82 1.507(4) yes . . C78 C79 1.381(4) yes . . C79 C80 1.390(3) yes . . C79 C83 1.508(3) yes . . C80 C81 1.393(3) yes . . C81 C84 1.510(3) yes . . C85 C86 1.365(5) yes . . C85 C90 1.371(4) yes . . C86 C87 1.383(5) yes . . C87 C88 1.383(5) yes . . C88 C89 1.368(6) yes . . C89 C90 1.378(5) yes . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C2 C1 C24 119.61(18) yes . . . C1 C2 C3 121.2(2) yes . . . C2 C3 C4 120.1(2) yes . . . C3 C4 C5 119.05(18) yes . . . C4 C5 C6 129.21(17) yes . . . C4 C5 C24 121.5(2) yes . . . C6 C5 C24 109.25(19) yes . . . C5 C6 C7 108.27(17) yes . . . C5 C6 C25 119.89(19) yes . . . C7 C6 C25 131.6(2) yes . . . C6 C7 C8 133.83(19) yes . . . C6 C7 C23 108.6(2) yes . . . C8 C7 C23 117.60(17) yes . . . C7 C8 C9 133.75(18) yes . . . C7 C8 C16 117.70(18) yes . . . C9 C8 C16 108.5(2) yes . . . C8 C9 C10 108.36(17) yes . . . C8 C9 C34 129.6(2) yes . . . C10 C9 C34 121.4(2) yes . . . C9 C10 C11 129.5(2) yes . . . C9 C10 C15 109.4(2) yes . . . C11 C10 C15 121.0(2) yes . . . C10 C11 C12 119.0(2) yes . . . C11 C12 C13 120.4(3) yes . . . C12 C13 C14 121.2(3) yes . . . C13 C14 C15 119.1(2) yes . . . C10 C15 C14 119.3(2) yes . . . C10 C15 C16 106.46(19) yes . . . C14 C15 C16 133.9(2) yes . . . C8 C16 C15 107.26(17) yes . . . C8 C16 C17 121.7(2) yes . . . C15 C16 C17 130.98(19) yes . . . C16 C17 C18 123.1(2) yes . . . C16 C17 C22 119.72(18) yes . . . C18 C17 C22 116.92(19) yes . . . C17 C18 C19 122.8(2) yes . . . C18 C19 C20 125.24(19) yes . . . C19 C20 C21 113.59(17) yes . . . C19 C20 C65 109.69(17) yes . . . C21 C20 C65 109.57(15) yes . . . C20 C21 C22 116.29(18) yes . . . C20 C21 C58 107.73(14) yes . . . C22 C21 C58 111.65(16) yes . . . C17 C22 C21 118.97(17) yes . . . C17 C22 C23 119.70(18) yes . . . C21 C22 C23 121.2(2) yes . . . C7 C23 C22 121.2(2) yes . . . C7 C23 C24 107.17(16) yes . . . C22 C23 C24 131.33(19) yes . . . C1 C24 C5 118.4(2) yes . . . C1 C24 C23 135.15(17) yes . . . C5 C24 C23 106.39(18) yes . . . C6 C25 C26 121.38(18) yes . . . C6 C25 C30 118.71(18) yes . . . C26 C25 C30 119.62(18) yes . . . C25 C26 C27 118.96(19) yes . . . C25 C26 C31 121.86(18) yes . . . C27 C26 C31 119.19(19) yes . . . C26 C27 C28 122.3(2) yes . . . C27 C28 C29 117.83(19) yes . . . C27 C28 C32 121.5(2) yes . . . C29 C28 C32 120.7(2) yes . . . C28 C29 C30 122.1(2) yes . . . C25 C30 C29 119.1(2) yes . . . C25 C30 C33 120.26(18) yes . . . C29 C30 C33 120.62(19) yes . . . C9 C34 C35 118.84(17) yes . . . C9 C34 C39 120.88(19) yes . . . C35 C34 C39 120.03(19) yes . . . C34 C35 C36 118.88(19) yes . . . C34 C35 C40 120.57(19) yes . . . C36 C35 C40 120.5(2) yes . . . C35 C36 C37 122.1(2) yes . . . C36 C37 C38 117.9(2) yes . . . C36 C37 C41 120.7(2) yes . . . C38 C37 C41 121.3(2) yes . . . C37 C38 C39 122.4(2) yes . . . C34 C39 C38 118.5(2) yes . . . C34 C39 C42 121.43(19) yes . . . C38 C39 C42 120.05(19) yes . . . C44 C43 C66 119.1(2) yes . . . C43 C44 C45 120.7(2) yes . . . C44 C45 C46 121.1(2) yes . . . C45 C46 C47 118.3(2) yes . . . C46 C47 C48 129.3(2) yes . . . C46 C47 C66 120.8(2) yes . . . C48 C47 C66 109.84(18) yes . . . C47 C48 C49 108.2(2) yes . . . C47 C48 C67 121.27(18) yes . . . C49 C48 C67 130.24(19) yes . . . C48 C49 C50 136.7(2) yes . . . C48 C49 C65 110.73(18) yes . . . C50 C49 C65 112.22(18) yes . . . C49 C50 C51 137.3(2) yes . . . C49 C50 C58 111.83(18) yes . . . C51 C50 C58 110.85(17) yes . . . C50 C51 C52 108.42(19) yes . . . C50 C51 C76 128.98(18) yes . . . C52 C51 C76 122.05(18) yes . . . C51 C52 C53 129.7(2) yes . . . C51 C52 C57 109.75(18) yes . . . C53 C52 C57 120.51(19) yes . . . C52 C53 C54 118.7(2) yes . . . C53 C54 C55 120.9(2) yes . . . C54 C55 C56 120.9(2) yes . . . C55 C56 C57 118.7(2) yes . . . C52 C57 C56 120.29(19) yes . . . C52 C57 C58 108.25(17) yes . . . C56 C57 C58 131.5(2) yes . . . C21 C58 C50 103.70(16) yes . . . C21 C58 C57 116.03(15) yes . . . C21 C58 C59 109.65(17) yes . . . C50 C58 C57 102.61(17) yes . . . C50 C58 C59 107.52(15) yes . . . C57 C58 C59 115.96(17) yes . . . C58 C59 C60 126.66(18) yes . . . C58 C59 C64 113.86(18) yes . . . C60 C59 C64 119.4(2) yes . . . C59 C60 C61 119.51(19) yes . . . C60 C61 C62 120.6(2) yes . . . C61 C62 C63 120.4(2) yes . . . C62 C63 C64 119.32(19) yes . . . C59 C64 C63 120.6(2) yes . . . C59 C64 C65 112.61(18) yes . . . C63 C64 C65 126.74(18) yes . . . C20 C65 C49 106.52(16) yes . . . C20 C65 C64 105.14(16) yes . . . C20 C65 C66 111.38(15) yes . . . C49 C65 C64 109.98(16) yes . . . C49 C65 C66 102.93(17) yes . . . C64 C65 C66 120.24(18) yes . . . C43 C66 C47 120.00(19) yes . . . C43 C66 C65 132.1(2) yes . . . C47 C66 C65 107.82(19) yes . . . C48 C67 C68 121.9(2) yes . . . C48 C67 C72 118.16(18) yes . . . C68 C67 C72 119.8(2) yes . . . C67 C68 C69 118.9(2) yes . . . C67 C68 C73 120.6(2) yes . . . C69 C68 C73 120.45(19) yes . . . C68 C69 C70 122.1(2) yes . . . C69 C70 C71 117.9(3) yes . . . C69 C70 C74 121.7(2) yes . . . C71 C70 C74 120.4(3) yes . . . C70 C71 C72 122.1(2) yes . . . C67 C72 C71 118.91(19) yes . . . C67 C72 C75 120.6(2) yes . . . C71 C72 C75 120.5(2) yes . . . C51 C76 C77 117.3(2) yes . . . C51 C76 C81 122.19(17) yes . . . C77 C76 C81 120.4(2) yes . . . C76 C77 C78 118.8(2) yes . . . C76 C77 C82 120.61(19) yes . . . C78 C77 C82 120.63(19) yes . . . C77 C78 C79 121.9(2) yes . . . C78 C79 C80 118.2(2) yes . . . C78 C79 C83 121.2(2) yes . . . C80 C79 C83 120.6(2) yes . . . C79 C80 C81 121.9(2) yes . . . C76 C81 C80 118.77(19) yes . . . C76 C81 C84 121.10(19) yes . . . C80 C81 C84 120.1(2) yes . . . Cl1 C85 C86 121.8(3) yes . . . Cl1 C85 C90 119.9(4) yes . . . C86 C85 C90 118.3(3) yes . . . C85 C86 C87 122.0(3) yes . . . C86 C87 C88 118.6(4) yes . . . C87 C88 C89 119.9(3) yes . . . C88 C89 C90 120.1(3) yes . . . C85 C90 C89 121.0(3) yes . . . #============================================================================== #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 960648'