Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 loop_ _publ_author_name 'Morris Bullock' 'Vladimir K. Dioumaev' 'James A. Franz' 'Jonathan Hanson' 'David J. Szalda' _publ_contact_author_name 'Dr Morris Bullock' _publ_contact_author_address ; Chemistry Brookhaven National Laboratory Building 555 Upton New York 11973 UNITED STATES OF AMERICA ; _publ_contact_author_email BULLOCK@BNL.GOV _publ_section_title ; An N-Heterocyclic Carbene as a Bidentate Hemilabile Ligand: A Synchrotron X-ray Diffraction and Density Functional Theory Study ; data_wvlad-1 _database_code_CSD 203785 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H30 N2 O2 W' _chemical_formula_sum 'C28 H30 N2 O2 W' _chemical_formula_weight 610.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9340(18) _cell_length_b 11.258(2) _cell_length_c 13.631(3) _cell_angle_alpha 80.97(3) _cell_angle_beta 72.96(3) _cell_angle_gamma 70.79(3) _cell_volume 1235.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 14.9 _cell_measurement_theta_max 16.8 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.641 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 604 _exptl_absorpt_coefficient_mu 4.704 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4150 _exptl_absorpt_correction_T_max 0.6605 _exptl_absorpt_process_details 'psi scans' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius CAD-4' _diffrn_measurement_method \q/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% <1% _diffrn_reflns_number 5652 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0536 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 27.47 _reflns_number_total 5652 _reflns_number_gt 4355 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD-4 (Enraf-Nonius, 1977)' _computing_cell_refinement 'CAD-4 (Enraf-Nonius, 1977)' _computing_data_reduction 'XCAD4VAX (Sheldrick, 1993)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0395P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5652 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0681 _refine_ls_R_factor_gt 0.0284 _refine_ls_wR_factor_ref 0.0724 _refine_ls_wR_factor_gt 0.0656 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group W1 W -0.12465(2) 0.786462(17) 0.189093(15) 0.03447(7) Uani 1 1 d . . . H1 H -0.2810 0.9070 0.1440 0.104(5) Uiso 1 1 d . . . C11 C -0.1101(6) 0.8244(5) 0.3191(4) 0.0493(12) Uani 1 1 d . . . O11 O -0.0945(6) 0.8497(4) 0.3953(3) 0.0770(13) Uani 1 1 d . . . C12 C -0.1210(6) 0.9588(5) 0.1623(4) 0.0490(12) Uani 1 1 d . . . O12 O -0.1148(6) 1.0624(4) 0.1441(4) 0.0795(13) Uani 1 1 d . . . C131 C 0.0432(7) 0.5786(5) 0.1824(5) 0.0561(14) Uani 1 1 d . . . H131 H 0.0361 0.5240 0.2411 0.104(5) Uiso 1 1 calc R . . C132 C -0.0451(7) 0.5978(5) 0.1076(5) 0.0607(15) Uani 1 1 d . . . H132 H -0.1218 0.5581 0.1084 0.104(5) Uiso 1 1 calc R . . C133 C 0.0038(7) 0.6883(6) 0.0313(4) 0.0576(14) Uani 1 1 d . . . H133 H -0.0349 0.7180 -0.0270 0.104(5) Uiso 1 1 calc R . . C134 C 0.1198(6) 0.7251(5) 0.0584(4) 0.0547(14) Uani 1 1 d . . . H134 H 0.1716 0.7837 0.0215 0.104(5) Uiso 1 1 calc R . . C135 C 0.1448(6) 0.6589(5) 0.1503(5) 0.0532(13) Uani 1 1 d . . . H135 H 0.2164 0.6661 0.1851 0.104(5) Uiso 1 1 calc R . . C111 C -0.3651(5) 0.7800(4) 0.2855(4) 0.0378(10) Uani 1 1 d . . . N112 N -0.5105(5) 0.8755(4) 0.3039(3) 0.0454(10) Uani 1 1 d . . . C113 C -0.6335(7) 0.8392(5) 0.3768(5) 0.0666(18) Uani 1 1 d . . . H113 H -0.7410 0.8889 0.4015 0.104(5) Uiso 1 1 calc R . . C114 C -0.5690(7) 0.7199(5) 0.4050(5) 0.0684(18) Uani 1 1 d . . . H114 H -0.6232 0.6700 0.4537 0.104(5) Uiso 1 1 calc R . . N115 N -0.4081(5) 0.6825(4) 0.3497(4) 0.0477(10) Uani 1 1 d . . . C121 C -0.5424(5) 0.9976(4) 0.2472(4) 0.0396(10) Uani 1 1 d . . . C122 C -0.5123(6) 1.0980(4) 0.2770(4) 0.0434(11) Uani 1 1 d . . . C123 C -0.5416(6) 1.2101(4) 0.2166(4) 0.0463(12) Uani 1 1 d . . . H123 H -0.5240 1.2790 0.2360 0.104(5) Uiso 1 1 calc R . . C124 C -0.5954(6) 1.2243(4) 0.1296(4) 0.0480(12) Uani 1 1 d . . . C125 C -0.6333(6) 1.1242(5) 0.1067(5) 0.0545(14) Uani 1 1 d . . . H125 H -0.6774 1.1341 0.0510 0.104(5) Uiso 1 1 calc R . . C126 C -0.6082(6) 1.0100(5) 0.1634(4) 0.0487(13) Uani 1 1 d . . . C127 C -0.4548(8) 1.0885(5) 0.3726(4) 0.0629(16) Uani 1 1 d . . . H271 H -0.4406 1.1674 0.3796 0.104(5) Uiso 1 1 calc R . . H272 H -0.3522 1.0230 0.3670 0.104(5) Uiso 1 1 calc R . . H273 H -0.5350 1.0691 0.4318 0.104(5) Uiso 1 1 calc R . . C128 C -0.6119(8) 1.3454(5) 0.0622(5) 0.0641(16) Uani 1 1 d . . . H281 H -0.6492 1.3384 0.0047 0.104(5) Uiso 1 1 calc R . . H282 H -0.5073 1.3609 0.0377 0.104(5) Uiso 1 1 calc R . . H283 H -0.6897 1.4140 0.1012 0.104(5) Uiso 1 1 calc R . . C129 C -0.6546(8) 0.9042(6) 0.1365(6) 0.0715(18) Uani 1 1 d . . . H291 H -0.6315 0.8328 0.1845 0.104(5) Uiso 1 1 calc R . . H292 H -0.5923 0.8809 0.0683 0.104(5) Uiso 1 1 calc R . . H293 H -0.7696 0.9316 0.1397 0.104(5) Uiso 1 1 calc R . . C151 C -0.3075(6) 0.5534(4) 0.3539(4) 0.0440(11) Uani 1 1 d . . . C152 C -0.3051(6) 0.4739(5) 0.2839(4) 0.0472(12) Uani 1 1 d . . . C153 C -0.2037(6) 0.3500(5) 0.2858(4) 0.0469(12) Uani 1 1 d . . . H153 H -0.1979 0.2971 0.2379 0.104(5) Uiso 1 1 calc R . . C154 C -0.1115(6) 0.3033(5) 0.3565(4) 0.0472(12) Uani 1 1 d . . . C155 C -0.1246(6) 0.3843(5) 0.4274(4) 0.0500(13) Uani 1 1 d . . . H155 H -0.0639 0.3537 0.4759 0.104(5) Uiso 1 1 calc R . . C156 C -0.2238(6) 0.5090(5) 0.4299(4) 0.0457(12) Uani 1 1 d . . . C157 C -0.4103(7) 0.5191(5) 0.2093(5) 0.0637(16) Uani 1 1 d . . . H571 H -0.4709 0.6065 0.2177 0.104(5) Uiso 1 1 calc R . . H572 H -0.4854 0.4705 0.2223 0.104(5) Uiso 1 1 calc R . . H573 H -0.3419 0.5092 0.1404 0.104(5) Uiso 1 1 calc R . . C158 C -0.0012(7) 0.1689(5) 0.3565(5) 0.0673(16) Uani 1 1 d . . . H581 H 0.0535 0.1534 0.4103 0.104(5) Uiso 1 1 calc R . . H582 H 0.0789 0.1555 0.2913 0.104(5) Uiso 1 1 calc R . . H583 H -0.0659 0.1124 0.3678 0.104(5) Uiso 1 1 calc R . . C159 C -0.2441(9) 0.5904(6) 0.5137(5) 0.0684(17) Uani 1 1 d . . . H591 H -0.1775 0.5433 0.5590 0.104(5) Uiso 1 1 calc R . . H592 H -0.3571 0.6161 0.5519 0.104(5) Uiso 1 1 calc R . . H593 H -0.2106 0.6636 0.4835 0.104(5) 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 W1 0.02984(9) 0.03164(9) 0.03993(11) -0.00193(6) -0.00402(7) -0.01124(6) C11 0.050(3) 0.046(3) 0.055(3) -0.001(2) -0.013(3) -0.018(2) O11 0.104(4) 0.079(3) 0.065(3) -0.005(2) -0.041(3) -0.032(3) C12 0.044(3) 0.044(3) 0.051(3) -0.001(2) 0.004(2) -0.019(2) O12 0.094(3) 0.042(2) 0.094(3) 0.007(2) -0.002(3) -0.035(2) C131 0.047(3) 0.039(3) 0.064(4) -0.003(2) 0.001(3) -0.003(2) C132 0.050(3) 0.049(3) 0.077(4) -0.029(3) 0.009(3) -0.018(3) C133 0.050(3) 0.062(4) 0.053(3) -0.017(3) 0.002(3) -0.016(3) C134 0.038(3) 0.050(3) 0.064(4) -0.006(3) 0.008(2) -0.015(2) C135 0.031(2) 0.050(3) 0.071(4) -0.011(3) -0.007(2) -0.006(2) C111 0.037(2) 0.028(2) 0.046(3) -0.0039(19) -0.004(2) -0.0116(18) N112 0.035(2) 0.0294(19) 0.059(3) -0.0012(18) 0.0037(19) -0.0077(16) C113 0.039(3) 0.041(3) 0.092(5) 0.000(3) 0.019(3) -0.009(2) C114 0.040(3) 0.050(3) 0.092(5) 0.004(3) 0.018(3) -0.019(2) N115 0.041(2) 0.030(2) 0.063(3) 0.0039(19) 0.001(2) -0.0151(17) C121 0.031(2) 0.030(2) 0.050(3) -0.005(2) -0.001(2) -0.0049(18) C122 0.043(3) 0.032(2) 0.047(3) -0.006(2) -0.004(2) -0.006(2) C123 0.050(3) 0.032(2) 0.050(3) -0.006(2) -0.004(2) -0.009(2) C124 0.044(3) 0.031(2) 0.056(3) -0.004(2) -0.007(2) 0.000(2) C125 0.046(3) 0.050(3) 0.067(4) -0.009(3) -0.024(3) -0.003(2) C126 0.030(2) 0.041(3) 0.071(4) -0.015(2) -0.008(2) -0.004(2) C127 0.089(4) 0.043(3) 0.051(3) -0.009(2) -0.018(3) -0.010(3) C128 0.074(4) 0.038(3) 0.067(4) 0.003(3) -0.018(3) -0.003(3) C129 0.063(4) 0.059(4) 0.103(5) -0.020(4) -0.023(4) -0.025(3) C151 0.036(2) 0.030(2) 0.061(3) 0.004(2) -0.002(2) -0.0152(19) C152 0.048(3) 0.039(3) 0.057(3) 0.008(2) -0.012(2) -0.022(2) C153 0.047(3) 0.038(3) 0.056(3) -0.002(2) -0.008(2) -0.018(2) C154 0.042(3) 0.036(2) 0.056(3) 0.003(2) 0.000(2) -0.015(2) C155 0.045(3) 0.049(3) 0.051(3) 0.009(2) -0.006(2) -0.019(2) C156 0.044(3) 0.039(3) 0.049(3) 0.002(2) 0.000(2) -0.019(2) C157 0.068(4) 0.050(3) 0.086(4) 0.014(3) -0.036(3) -0.029(3) C158 0.062(4) 0.045(3) 0.080(4) 0.002(3) -0.016(3) -0.002(3) C159 0.084(5) 0.058(4) 0.063(4) -0.006(3) -0.012(3) -0.027(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 W1 C12 1.927(5) . y W1 C11 1.936(6) . y W1 C111 2.183(5) . y W1 C135 2.314(5) . ? W1 C131 2.326(5) . ? W1 C134 2.352(5) . ? W1 C132 2.352(5) . ? W1 C133 2.373(5) . ? C11 O11 1.175(6) . y C12 O12 1.169(6) . y C131 C132 1.413(8) . ? C131 C135 1.420(8) . ? C132 C133 1.416(8) . ? C133 C134 1.392(8) . ? C134 C135 1.391(8) . ? C111 N112 1.371(6) . ? C111 N115 1.378(6) . ? N112 C113 1.375(6) . ? N112 C121 1.451(6) . ? C113 C114 1.320(8) . ? C114 N115 1.371(7) . ? N115 C151 1.438(6) . ? C121 C122 1.386(7) . ? C121 C126 1.400(7) . ? C122 C123 1.386(7) . ? C122 C127 1.512(7) . ? C123 C124 1.374(7) . ? C124 C125 1.381(7) . ? C124 C128 1.510(7) . ? C125 C126 1.378(8) . ? C126 C129 1.508(7) . ? C151 C156 1.388(7) . ? C151 C152 1.399(7) . ? C152 C153 1.392(7) . ? C152 C157 1.503(7) . ? C153 C154 1.380(7) . ? C154 C155 1.386(8) . ? C154 C158 1.510(7) . ? C155 C156 1.391(7) . ? C156 C159 1.508(8) . ? 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 C12 W1 C11 77.7(2) . . y C12 W1 C111 109.68(19) . . y C11 W1 C111 80.3(2) . . y C12 W1 C135 107.4(2) . . ? C11 W1 C135 92.1(2) . . ? C111 W1 C135 139.39(19) . . ? C12 W1 C131 143.1(2) . . ? C11 W1 C131 99.4(2) . . ? C111 W1 C131 106.00(18) . . ? C135 W1 C131 35.64(19) . . ? C12 W1 C134 89.8(2) . . ? C11 W1 C134 118.0(2) . . ? C111 W1 C134 156.40(19) . . ? C135 W1 C134 34.68(19) . . ? C131 W1 C134 58.5(2) . . ? C12 W1 C132 141.9(2) . . ? C11 W1 C132 133.1(2) . . ? C111 W1 C132 98.95(18) . . ? C135 W1 C132 58.3(2) . . ? C131 W1 C132 35.2(2) . . ? C134 W1 C132 57.87(19) . . ? C12 W1 C133 107.0(2) . . ? C11 W1 C133 149.5(2) . . ? C111 W1 C133 123.57(19) . . ? C135 W1 C133 57.5(2) . . ? C131 W1 C133 58.2(2) . . ? C134 W1 C133 34.26(19) . . ? C132 W1 C133 34.9(2) . . ? O11 C11 W1 176.6(5) . . y O12 C12 W1 178.2(5) . . y C132 C131 C135 106.7(5) . . ? C132 C131 W1 73.4(3) . . ? C135 C131 W1 71.7(3) . . ? C131 C132 C133 107.9(5) . . ? C131 C132 W1 71.4(3) . . ? C133 C132 W1 73.4(3) . . ? C134 C133 C132 108.3(6) . . ? C134 C133 W1 72.0(3) . . ? C132 C133 W1 71.8(3) . . ? C135 C134 C133 108.2(5) . . ? C135 C134 W1 71.1(3) . . ? C133 C134 W1 73.7(3) . . ? C134 C135 C131 108.9(5) . . ? C134 C135 W1 74.2(3) . . ? C131 C135 W1 72.6(3) . . ? N112 C111 N115 101.8(4) . . y N112 C111 W1 128.8(3) . . y N115 C111 W1 129.3(3) . . y C111 N112 C113 112.3(4) . . ? C111 N112 C121 125.8(4) . . ? C113 N112 C121 121.6(4) . . ? C114 C113 N112 106.5(5) . . ? C113 C114 N115 108.0(5) . . ? C114 N115 C111 111.4(4) . . ? C114 N115 C151 121.9(4) . . ? C111 N115 C151 126.3(4) . . ? C122 C121 C126 121.8(4) . . ? C122 C121 N112 121.0(5) . . ? C126 C121 N112 117.1(4) . . ? C123 C122 C121 117.1(5) . . ? C123 C122 C127 120.7(5) . . ? C121 C122 C127 122.1(5) . . ? C124 C123 C122 123.1(5) . . ? C123 C124 C125 117.5(5) . . ? C123 C124 C128 120.7(5) . . ? C125 C124 C128 121.8(5) . . ? C126 C125 C124 122.5(5) . . ? C125 C126 C121 117.6(5) . . ? C125 C126 C129 120.4(5) . . ? C121 C126 C129 121.9(5) . . ? C156 C151 C152 121.8(4) . . ? C156 C151 N115 120.0(5) . . ? C152 C151 N115 118.2(5) . . ? C153 C152 C151 118.2(5) . . ? C153 C152 C157 120.3(5) . . ? C151 C152 C157 121.5(5) . . ? C154 C153 C152 122.0(5) . . ? C153 C154 C155 117.5(5) . . ? C153 C154 C158 121.1(5) . . ? C155 C154 C158 121.5(5) . . ? C154 C155 C156 123.4(5) . . ? C151 C156 C155 116.9(5) . . ? C151 C156 C159 121.7(5) . . ? C155 C156 C159 121.4(5) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.999 _refine_diff_density_min -0.605 _refine_diff_density_rms 0.132 data_wvladfst _database_code_CSD 203786 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; '( C28 H29 N2 O2 W ), ( C24 F20 B ), ( C3.5 H4 )' ; _chemical_formula_sum 'C55.50 H33 B F20 N2 O2 W' _chemical_formula_weight 1334.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0048 0.0027 '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' B B 0.0014 0.0012 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0088 0.0056 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0153 0.0102 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0246 0.0172 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' W W -3.4133 10.0614 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c 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 18.262(4) _cell_length_b 17.725(4) _cell_length_c 17.657(4) _cell_angle_alpha 90.00 _cell_angle_beta 113.87(3) _cell_angle_gamma 90.00 _cell_volume 5226.6(18) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour black _exptl_crystal_size_max .100 _exptl_crystal_size_mid .050 _exptl_crystal_size_min .010 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.696 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2620 _exptl_absorpt_coefficient_mu 2.327 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Data were collected at beamline X7B at the Brookhaven National Laboratory NSLS, using the rotation method. Data were recorded on image plates. A total of 60 plates were measured, where each rotation was 3 degrees in psi. This was followed by 36 rapid scans of 5 degrees each to measure the overloads. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.90350 _diffrn_radiation_type ? _diffrn_radiation_source 'National Synchrotron Light Source beamline x7b' _diffrn_radiation_monochromator Si(111) _diffrn_measurement_device_type Huber _diffrn_measurement_method 'mar dectector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4800 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0283 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 28.25 _reflns_number_total 4800 _reflns_number_gt 4654 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; see M.J. Gray etal for a description of data collection at beamline x7b ; _computing_cell_refinement ; average of cell contants determined on each image plate ; _computing_data_reduction 'DENZO, SCALEPACK (Otwinowski)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0862P)^2^+53.9393P] 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 4800 _refine_ls_number_parameters 749 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0585 _refine_ls_R_factor_gt 0.0573 _refine_ls_wR_factor_ref 0.1540 _refine_ls_wR_factor_gt 0.1528 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.447 _refine_ls_shift/su_mean 0.009 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 W1 W 0.27936(3) 0.32989(2) 0.85396(3) 0.0466(3) Uani 1 1 d . . . C1 C 0.4022(7) 0.4040(8) 0.9005(9) 0.066(4) Uani 1 1 d . . . H1 H 0.4036 0.4554 0.8862 0.104(9) Uiso 1 1 calc R . . C2 C 0.4047(8) 0.3388(10) 0.8528(10) 0.075(4) Uani 1 1 d . . . H2 H 0.4061 0.3399 0.7996 0.104(9) Uiso 1 1 calc R . . C3 C 0.4048(8) 0.2732(10) 0.8982(10) 0.079(5) Uani 1 1 d . . . H3 H 0.4078 0.2224 0.8827 0.104(9) Uiso 1 1 calc R . . C4 C 0.3994(9) 0.2989(8) 0.9713(9) 0.074(4) Uani 1 1 d . . . H4 H 0.3974 0.2677 1.0141 0.104(9) Uiso 1 1 calc R . . C5 C 0.3973(7) 0.3766(7) 0.9706(9) 0.064(4) Uani 1 1 d . . . H5 H 0.3931 0.4070 1.0130 0.104(9) Uiso 1 1 calc R . . C6 C 0.2228(8) 0.3617(7) 0.9200(10) 0.069(4) Uani 1 1 d . . . O6 O 0.1901(6) 0.3786(6) 0.9610(7) 0.091(3) Uani 1 1 d . . . C7 C 0.2230(11) 0.2389(9) 0.8590(10) 0.095(5) Uani 1 1 d . . . O7 O 0.1916(8) 0.1837(6) 0.8685(9) 0.116(5) Uani 1 1 d . . . C11 C 0.2329(6) 0.3048(5) 0.7214(7) 0.040(3) Uani 1 1 d . . . N12 N 0.1657(5) 0.3471(4) 0.6735(7) 0.036(2) Uani 1 1 d . . . C13 C 0.1350(8) 0.3367(6) 0.5892(10) 0.052(4) Uani 1 1 d . . . H13 H 0.0897 0.3601 0.5477 0.104(9) Uiso 1 1 calc R . . C14 C 0.1856(8) 0.2847(6) 0.5799(9) 0.053(3) Uani 1 1 d . . . H14 H 0.1820 0.2646 0.5286 0.104(9) Uiso 1 1 calc R . . N15 N 0.2442(5) 0.2656(4) 0.6585(6) 0.036(2) Uani 1 1 d . . . C121 C 0.1406(6) 0.3963(5) 0.7228(7) 0.040(3) Uani 1 1 d . . . C122 C 0.1842(6) 0.4647(5) 0.7522(7) 0.041(3) Uani 1 1 d . . . C123 C 0.1558(7) 0.5139(6) 0.7944(7) 0.049(3) Uani 1 1 d . . . H123 H 0.1844 0.5590 0.8170 0.104(9) Uiso 1 1 calc R . . C124 C 0.0851(7) 0.4981(6) 0.8043(8) 0.055(3) Uani 1 1 d . . . C125 C 0.0434(7) 0.4291(6) 0.7692(8) 0.057(3) Uani 1 1 d . . . H125 H -0.0056 0.4192 0.7740 0.104(9) Uiso 1 1 calc R . . C126 C 0.0698(6) 0.3780(6) 0.7301(8) 0.047(3) Uani 1 1 d . . . C127 C 0.2477(6) 0.4925(5) 0.7271(7) 0.045(3) Uani 1 1 d . . . H271 H 0.2646 0.5431 0.7499 0.104(9) Uiso 1 1 calc R . . H272 H 0.2269 0.4945 0.6665 0.104(9) Uiso 1 1 calc R . . H273 H 0.2937 0.4582 0.7482 0.104(9) Uiso 1 1 calc R . . C128 C 0.0536(9) 0.5522(8) 0.8464(10) 0.084(5) Uani 1 1 d . . . H281 H 0.0896 0.5958 0.8646 0.104(9) Uiso 1 1 calc R . . H282 H 0.0498 0.5280 0.8946 0.104(9) Uiso 1 1 calc R . . H283 H 0.0003 0.5690 0.8081 0.104(9) Uiso 1 1 calc R . . C129 C 0.0239(7) 0.3051(6) 0.6936(9) 0.065(4) Uani 1 1 d . . . H291 H -0.0254 0.3038 0.7031 0.104(9) Uiso 1 1 calc R . . H292 H 0.0573 0.2616 0.7205 0.104(9) Uiso 1 1 calc R . . H293 H 0.0103 0.3035 0.6340 0.104(9) Uiso 1 1 calc R . . C151 C 0.3112(7) 0.2135(5) 0.6749(7) 0.043(3) Uani 1 1 d . . . C152 C 0.3778(7) 0.2378(5) 0.6665(7) 0.041(3) Uani 1 1 d . . . C153 C 0.4411(6) 0.1863(5) 0.6819(7) 0.036(3) Uani 1 1 d . . . H153 H 0.4878 0.2028 0.6755 0.104(9) Uiso 1 1 calc R . . C154 C 0.4376(7) 0.1128(5) 0.7060(7) 0.044(3) Uani 1 1 d . . . C155 C 0.3687(7) 0.0897(6) 0.7133(8) 0.054(3) Uani 1 1 d . . . H155 H 0.3653 0.0392 0.7294 0.104(9) Uiso 1 1 calc R . . C156 C 0.3039(7) 0.1379(6) 0.6978(8) 0.057(3) Uani 1 1 d . . . C157 C 0.3812(7) 0.3173(5) 0.6342(8) 0.052(3) Uani 1 1 d . . . H571 H 0.3548 0.3528 0.6575 0.104(9) Uiso 1 1 calc R . . H572 H 0.3539 0.3176 0.5736 0.104(9) Uiso 1 1 calc R . . H573 H 0.4373 0.3322 0.6507 0.104(9) Uiso 1 1 calc R . . C158 C 0.5063(7) 0.0577(6) 0.7217(8) 0.060(3) Uani 1 1 d . . . H581 H 0.5532 0.0739 0.7705 0.104(9) Uiso 1 1 calc R . . H582 H 0.5198 0.0566 0.6734 0.104(9) Uiso 1 1 calc R . . H583 H 0.4901 0.0071 0.7313 0.104(9) Uiso 1 1 calc R . . C159 C 0.2278(8) 0.1105(7) 0.7048(12) 0.098(6) Uani 1 1 d . . . H591 H 0.2015 0.1531 0.7191 0.104(9) Uiso 1 1 calc R . . H592 H 0.2414 0.0719 0.7481 0.104(9) Uiso 1 1 calc R . . H593 H 0.1915 0.0889 0.6518 0.104(9) Uiso 1 1 calc R . . B1 B 0.2703(7) 0.7984(6) 0.8120(8) 0.035(3) Uani 1 1 d . . . C61 C 0.3200(6) 0.7813(4) 0.7567(6) 0.029(2) Uani 1 1 d . . . C62 C 0.3731(6) 0.8309(5) 0.7444(7) 0.033(3) Uani 1 1 d . . . C63 C 0.4046(6) 0.8159(5) 0.6891(7) 0.040(3) Uani 1 1 d . . . C64 C 0.3853(6) 0.7505(6) 0.6417(7) 0.038(3) Uani 1 1 d . . . C65 C 0.3317(6) 0.7006(5) 0.6504(7) 0.039(3) Uani 1 1 d . . . C66 C 0.3004(6) 0.7184(5) 0.7057(7) 0.034(3) Uani 1 1 d . . . F62 F 0.3964(3) 0.8972(3) 0.7860(4) 0.0391(15) Uani 1 1 d . . . F63 F 0.4547(3) 0.8676(3) 0.6788(4) 0.0515(17) Uani 1 1 d . . . F64 F 0.4176(4) 0.7358(3) 0.5895(4) 0.0541(17) Uani 1 1 d . . . F65 F 0.3106(4) 0.6367(3) 0.6041(4) 0.0513(16) Uani 1 1 d . . . F66 F 0.2461(4) 0.6672(2) 0.7085(4) 0.0434(16) Uani 1 1 d . . . C71 C 0.3116(6) 0.8692(5) 0.8822(7) 0.030(3) Uani 1 1 d . . . C72 C 0.3930(7) 0.8678(5) 0.9392(7) 0.033(3) Uani 1 1 d . . . C73 C 0.4331(7) 0.9205(5) 1.0037(7) 0.042(3) Uani 1 1 d . . . C74 C 0.3877(9) 0.9793(5) 1.0114(8) 0.051(3) Uani 1 1 d . . . C75 C 0.3054(9) 0.9835(5) 0.9574(8) 0.053(4) Uani 1 1 d . . . C76 C 0.2673(7) 0.9297(5) 0.8925(7) 0.041(3) Uani 1 1 d . . . F72 F 0.4424(3) 0.8114(3) 0.9369(4) 0.0401(15) Uani 1 1 d . . . F73 F 0.5147(4) 0.9147(3) 1.0587(4) 0.0555(17) Uani 1 1 d . . . F74 F 0.4246(5) 1.0308(3) 1.0736(4) 0.069(2) Uani 1 1 d . . . F75 F 0.2599(5) 1.0397(3) 0.9648(5) 0.077(2) Uani 1 1 d . . . F76 F 0.1862(4) 0.9373(3) 0.8426(4) 0.0550(17) Uani 1 1 d . . . C81 C 0.1769(6) 0.8143(5) 0.7340(7) 0.037(3) Uani 1 1 d . . . C82 C 0.1626(7) 0.8767(5) 0.6815(8) 0.039(3) Uani 1 1 d . . . C83 C 0.0918(7) 0.8924(6) 0.6097(8) 0.043(3) Uani 1 1 d . . . C84 C 0.0271(7) 0.8416(7) 0.5828(8) 0.049(3) Uani 1 1 d . . . C85 C 0.0365(7) 0.7784(6) 0.6313(8) 0.046(3) Uani 1 1 d . . . C86 C 0.1089(7) 0.7654(5) 0.7032(7) 0.037(3) Uani 1 1 d . . . F82 F 0.2250(3) 0.9278(3) 0.7031(4) 0.0454(15) Uani 1 1 d . . . F83 F 0.0850(4) 0.9547(3) 0.5630(4) 0.0584(18) Uani 1 1 d . . . F84 F -0.0435(4) 0.8541(4) 0.5104(5) 0.067(2) Uani 1 1 d . . . F85 F -0.0274(4) 0.7294(4) 0.6067(4) 0.0646(19) Uani 1 1 d . . . F86 F 0.1117(3) 0.7007(3) 0.7463(4) 0.0469(16) Uani 1 1 d . . . C91 C 0.2775(6) 0.7275(5) 0.8776(7) 0.034(3) Uani 1 1 d . . . C92 C 0.3329(7) 0.6676(5) 0.9032(7) 0.038(3) Uani 1 1 d . . . C93 C 0.3374(7) 0.6140(5) 0.9622(7) 0.047(3) Uani 1 1 d . . . C94 C 0.2866(8) 0.6165(6) 0.9965(8) 0.057(3) Uani 1 1 d . . . C95 C 0.2310(8) 0.6746(6) 0.9761(8) 0.051(3) Uani 1 1 d . . . C96 C 0.2284(7) 0.7284(6) 0.9185(7) 0.046(3) Uani 1 1 d . . . F92 F 0.3874(4) 0.6588(3) 0.8727(4) 0.0457(16) Uani 1 1 d . . . F93 F 0.3938(4) 0.5572(3) 0.9840(4) 0.0660(19) Uani 1 1 d . . . F94 F 0.2892(5) 0.5630(4) 1.0533(4) 0.078(2) Uani 1 1 d . . . F95 F 0.1796(5) 0.6819(4) 1.0119(5) 0.073(2) Uani 1 1 d . . . F96 F 0.1739(4) 0.7870(3) 0.9012(4) 0.0526(17) Uani 1 1 d . . . C331 C 0.013(2) 0.5343(17) 0.5636(12) 0.105(8) Uani 1 1 d . . . C332 C -0.040(4) 0.504(4) 0.573(3) 0.098(15) Uani 0.50 1 d P . . C333 C 0.0573(19) 0.534(2) 0.495(3) 0.145(11) Uani 1 1 d . . . C334 C -0.110(2) 0.434(2) 0.506(3) 0.098(14) Uani 0.50 1 d P . . C335 C 0.065(3) 0.573(2) 0.561(6) 0.13(2) Uani 0.50 1 d P . . 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 W1 0.0547(4) 0.0423(3) 0.0475(6) 0.0098(2) 0.0256(4) 0.0064(2) C1 0.059(8) 0.087(10) 0.053(11) -0.006(8) 0.024(8) -0.002(7) C2 0.042(8) 0.138(15) 0.046(11) -0.005(10) 0.017(8) 0.003(8) C3 0.054(9) 0.105(12) 0.062(13) -0.002(10) 0.008(8) 0.039(8) C4 0.097(11) 0.069(9) 0.047(11) 0.017(7) 0.021(9) 0.027(8) C5 0.069(9) 0.063(8) 0.074(12) 0.007(7) 0.043(9) 0.009(6) C6 0.074(9) 0.064(8) 0.083(12) 0.031(8) 0.045(10) 0.017(7) O6 0.099(8) 0.106(8) 0.091(9) 0.034(6) 0.063(7) 0.028(6) C7 0.149(15) 0.068(10) 0.081(13) 0.031(8) 0.060(12) 0.056(10) O7 0.145(10) 0.057(6) 0.171(13) 0.056(7) 0.091(10) 0.001(6) C11 0.047(7) 0.017(5) 0.060(10) 0.010(6) 0.025(7) -0.005(5) N12 0.050(6) 0.027(4) 0.029(8) -0.003(4) 0.013(6) -0.006(4) C13 0.053(8) 0.043(7) 0.055(13) -0.005(6) 0.017(8) 0.005(5) C14 0.062(8) 0.046(7) 0.042(11) -0.007(6) 0.013(9) 0.001(6) N15 0.046(6) 0.026(4) 0.031(7) 0.004(4) 0.010(6) 0.004(4) C121 0.045(7) 0.027(5) 0.042(8) 0.009(5) 0.012(6) 0.007(5) C122 0.045(6) 0.039(6) 0.042(8) 0.000(5) 0.022(6) -0.002(5) C123 0.061(8) 0.042(6) 0.051(9) -0.008(6) 0.031(7) -0.005(5) C124 0.066(8) 0.052(7) 0.056(10) 0.006(6) 0.035(7) 0.010(6) C125 0.050(7) 0.057(7) 0.069(10) 0.014(7) 0.030(7) 0.000(6) C126 0.046(7) 0.039(6) 0.060(9) 0.008(6) 0.026(7) 0.002(5) C127 0.056(7) 0.020(5) 0.061(9) 0.006(5) 0.028(7) 0.001(5) C128 0.112(12) 0.068(9) 0.096(13) -0.009(8) 0.067(11) 0.005(8) C129 0.061(8) 0.049(7) 0.095(12) 0.004(7) 0.042(8) -0.007(6) C151 0.057(7) 0.026(5) 0.044(9) -0.002(5) 0.019(7) -0.001(5) C152 0.066(8) 0.023(5) 0.037(8) -0.002(5) 0.024(7) -0.004(5) C153 0.051(7) 0.031(5) 0.027(8) 0.007(5) 0.015(6) 0.007(5) C154 0.057(7) 0.027(6) 0.048(9) 0.002(5) 0.019(7) 0.008(5) C155 0.079(9) 0.024(5) 0.068(10) 0.000(5) 0.038(8) -0.001(6) C156 0.073(9) 0.029(6) 0.075(10) 0.001(6) 0.035(8) -0.003(6) C157 0.075(8) 0.026(5) 0.066(10) 0.008(5) 0.040(8) 0.006(5) C158 0.071(8) 0.038(6) 0.079(10) 0.006(6) 0.039(8) 0.016(6) C159 0.090(10) 0.030(6) 0.198(19) 0.005(8) 0.084(12) -0.007(6) B1 0.053(8) 0.018(5) 0.046(10) 0.002(5) 0.034(8) -0.001(5) C61 0.040(6) 0.018(5) 0.031(7) 0.003(4) 0.018(6) 0.006(4) C62 0.044(6) 0.027(6) 0.035(8) 0.000(5) 0.024(6) 0.003(4) C63 0.039(6) 0.031(5) 0.052(9) 0.005(5) 0.021(7) -0.001(5) C64 0.039(6) 0.047(6) 0.024(8) 0.001(5) 0.010(6) 0.006(5) C65 0.049(7) 0.021(5) 0.040(8) -0.004(5) 0.012(6) 0.004(5) C66 0.049(6) 0.021(5) 0.041(8) -0.001(5) 0.027(6) -0.001(4) F62 0.057(4) 0.020(3) 0.050(4) -0.006(3) 0.033(3) -0.006(2) F63 0.055(4) 0.049(3) 0.066(5) 0.002(3) 0.041(4) -0.008(3) F64 0.068(4) 0.060(4) 0.053(5) -0.007(3) 0.043(4) 0.003(3) F65 0.072(4) 0.038(3) 0.052(5) -0.015(3) 0.034(4) -0.002(3) F66 0.062(4) 0.022(3) 0.058(5) -0.012(2) 0.037(4) -0.012(2) C71 0.047(7) 0.020(5) 0.027(7) -0.002(4) 0.020(7) -0.003(4) C72 0.056(8) 0.021(5) 0.028(8) -0.003(5) 0.023(7) -0.009(5) C73 0.064(9) 0.029(6) 0.040(9) 0.006(6) 0.028(8) -0.005(5) C74 0.093(11) 0.025(6) 0.045(9) 0.000(6) 0.036(9) -0.005(6) C75 0.098(11) 0.026(6) 0.056(10) -0.004(6) 0.051(9) 0.009(6) C76 0.058(8) 0.036(6) 0.035(8) -0.001(6) 0.023(7) 0.005(5) F72 0.049(4) 0.030(3) 0.044(4) -0.003(3) 0.021(3) 0.000(3) F73 0.070(5) 0.046(3) 0.048(5) -0.006(3) 0.020(4) -0.016(3) F74 0.120(6) 0.031(3) 0.057(5) -0.022(3) 0.035(4) -0.014(4) F75 0.119(6) 0.041(4) 0.074(6) -0.018(3) 0.043(5) 0.025(4) F76 0.071(5) 0.042(3) 0.060(5) -0.006(3) 0.035(4) 0.017(3) C81 0.045(7) 0.031(5) 0.045(9) -0.009(5) 0.027(7) -0.003(5) C82 0.045(8) 0.037(6) 0.040(9) -0.006(6) 0.022(8) -0.001(5) C83 0.056(9) 0.042(6) 0.037(9) 0.003(6) 0.024(8) 0.009(6) C84 0.038(8) 0.072(9) 0.035(10) 0.002(7) 0.013(8) 0.013(6) C85 0.044(8) 0.049(7) 0.052(10) -0.007(6) 0.025(8) -0.004(6) C86 0.045(8) 0.039(6) 0.031(9) -0.009(5) 0.020(7) -0.001(5) F82 0.062(4) 0.026(3) 0.055(5) 0.006(3) 0.031(4) 0.003(3) F83 0.073(4) 0.051(4) 0.056(5) 0.018(3) 0.030(4) 0.017(3) F84 0.056(5) 0.086(5) 0.050(6) 0.006(4) 0.014(5) 0.005(4) F85 0.049(4) 0.079(5) 0.061(5) -0.008(4) 0.017(4) -0.019(4) F86 0.054(4) 0.041(3) 0.052(5) 0.000(3) 0.027(3) -0.013(3) C91 0.050(7) 0.026(5) 0.029(7) -0.010(5) 0.018(6) -0.010(5) C92 0.052(7) 0.024(5) 0.039(9) 0.000(5) 0.020(7) -0.005(5) C93 0.069(8) 0.025(6) 0.047(9) -0.003(5) 0.025(7) -0.004(5) C94 0.082(9) 0.033(6) 0.049(10) 0.002(6) 0.020(8) -0.013(6) C95 0.070(9) 0.061(8) 0.029(9) -0.009(6) 0.029(8) -0.032(7) C96 0.057(7) 0.039(6) 0.048(9) -0.011(6) 0.030(7) -0.014(5) F92 0.063(4) 0.028(3) 0.053(5) 0.003(3) 0.030(4) 0.007(3) F93 0.103(5) 0.031(3) 0.060(5) 0.009(3) 0.028(4) 0.003(3) F94 0.126(6) 0.055(4) 0.058(5) 0.016(4) 0.044(5) -0.027(4) F95 0.093(6) 0.087(5) 0.060(6) -0.002(4) 0.054(5) -0.028(4) F96 0.059(4) 0.057(4) 0.058(5) -0.004(3) 0.039(4) -0.003(3) C331 0.17(3) 0.079(16) 0.054(14) 0.021(13) 0.04(2) 0.074(17) C332 0.12(4) 0.11(3) 0.07(4) 0.05(3) 0.04(3) 0.06(3) C333 0.15(3) 0.12(3) 0.12(3) 0.04(2) 0.01(3) 0.09(2) C334 0.08(3) 0.11(3) 0.08(3) 0.05(2) 0.01(2) -0.01(2) C335 0.10(4) 0.07(3) 0.17(7) 0.04(4) -0.01(4) 0.05(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 W1 C6 1.928(15) . y W1 C7 1.934(19) . y W1 C11 2.188(12) . y W1 C2 2.303(12) . ? W1 C3 2.327(12) . ? W1 C4 2.392(14) . ? W1 C1 2.437(13) . ? W1 C5 2.445(15) . ? C1 C5 1.365(18) . ? C1 C2 1.44(2) . ? C2 C3 1.41(2) . ? C3 C4 1.41(2) . ? C4 C5 1.378(18) . ? C6 O6 1.150(15) . y C7 O7 1.180(18) . y C11 N15 1.393(13) . ? C11 N12 1.394(14) . ? N12 C13 1.374(16) . ? N12 C121 1.432(14) . ? C13 C14 1.362(15) . ? C14 N15 1.409(15) . ? N15 C151 1.466(13) . ? C121 C126 1.389(14) . ? C121 C122 1.428(14) . ? C122 C123 1.377(14) . ? C122 C127 1.485(13) . ? C123 C124 1.398(15) . ? C124 C125 1.441(17) . ? C124 C128 1.467(17) . ? C125 C126 1.341(16) . ? C126 C129 1.532(16) . ? C151 C152 1.353(14) . ? C151 C156 1.422(15) . ? C152 C153 1.411(14) . ? C152 C157 1.530(14) . ? C153 C154 1.380(14) . ? C154 C155 1.376(15) . ? C154 C158 1.526(14) . ? C155 C156 1.394(16) . ? C156 C159 1.524(16) . ? B1 C61 1.609(14) . ? B1 C91 1.677(15) . ? B1 C71 1.710(16) . ? B1 C81 1.727(18) . ? C61 C66 1.386(13) . ? C61 C62 1.390(13) . ? C62 C63 1.343(14) . ? C62 F62 1.360(11) . ? C63 F63 1.359(11) . ? C63 C64 1.390(15) . ? C64 F64 1.305(11) . ? C64 C65 1.374(14) . ? C65 C66 1.353(14) . ? C65 F65 1.358(11) . ? C66 F66 1.358(10) . ? C71 C76 1.398(13) . ? C71 C72 1.419(15) . ? C72 F72 1.358(11) . ? C72 C73 1.425(15) . ? C73 C74 1.371(15) . ? C73 F73 1.415(13) . ? C74 F74 1.377(14) . ? C74 C75 1.420(18) . ? C75 F75 1.338(12) . ? C75 C76 1.435(16) . ? C76 F76 1.391(13) . ? C81 C82 1.398(15) . ? C81 C86 1.430(14) . ? C82 F82 1.383(11) . ? C82 C83 1.425(16) . ? C83 F83 1.354(12) . ? C83 C84 1.407(16) . ? C84 C85 1.378(17) . ? C84 F84 1.418(14) . ? C85 F85 1.375(12) . ? C85 C86 1.434(16) . ? C86 F86 1.364(12) . ? C91 C96 1.360(14) . ? C91 C92 1.409(14) . ? C92 F92 1.319(12) . ? C92 C93 1.389(15) . ? C93 C94 1.298(16) . ? C93 F93 1.378(12) . ? C94 F94 1.368(13) . ? C94 C95 1.386(17) . ? C95 F95 1.334(13) . ? C95 C96 1.381(16) . ? C96 F96 1.384(12) . ? C331 C332 1.17(5) . ? C331 C335 1.18(5) . ? C331 C333 1.71(4) . ? C331 C333 1.76(4) 3_566 ? C332 C333 1.29(5) 3_566 ? C332 C334 1.83(11) . ? C333 C334 1.12(4) 3_566 ? C333 C332 1.29(5) 3_566 ? C333 C335 1.32(7) . ? C333 C331 1.76(4) 3_566 ? C334 C333 1.12(4) 3_566 ? C334 C335 1.70(13) 3_566 ? C335 C334 1.70(13) 3_566 ? 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 C6 W1 C7 77.9(6) . . y C6 W1 C11 129.5(5) . . y C7 W1 C11 84.1(5) . . y C6 W1 C2 139.7(6) . . ? C7 W1 C2 127.4(6) . . ? C11 W1 C2 87.7(5) . . ? C6 W1 C3 128.2(6) . . ? C7 W1 C3 95.4(6) . . ? C11 W1 C3 100.0(5) . . ? C2 W1 C3 35.5(5) . . ? C6 W1 C4 94.0(6) . . ? C7 W1 C4 95.0(6) . . ? C11 W1 C4 134.6(4) . . ? C2 W1 C4 57.2(5) . . ? C3 W1 C4 34.7(5) . . ? C6 W1 C1 106.5(6) . . ? C7 W1 C1 150.2(6) . . ? C11 W1 C1 112.1(4) . . ? C2 W1 C1 35.3(5) . . ? C3 W1 C1 58.2(6) . . ? C4 W1 C1 55.7(5) . . ? C6 W1 C5 84.0(5) . . ? C7 W1 C5 123.2(6) . . ? C11 W1 C5 142.9(4) . . ? C2 W1 C5 56.2(5) . . ? C3 W1 C5 56.7(5) . . ? C4 W1 C5 33.1(4) . . ? C1 W1 C5 32.5(4) . . ? C5 C1 C2 106.0(13) . . ? C5 C1 W1 74.1(8) . . ? C2 C1 W1 67.3(7) . . ? C3 C2 C1 108.7(14) . . ? C3 C2 W1 73.2(7) . . ? C1 C2 W1 77.4(7) . . ? C4 C3 C2 105.7(13) . . ? C4 C3 W1 75.1(8) . . ? C2 C3 W1 71.3(7) . . ? C5 C4 C3 109.1(13) . . ? C5 C4 W1 75.6(8) . . ? C3 C4 W1 70.1(7) . . ? C1 C5 C4 110.5(12) . . ? C1 C5 W1 73.4(8) . . ? C4 C5 W1 71.3(8) . . ? O6 C6 W1 177.7(11) . . ? O7 C7 W1 175.0(15) . . ? N15 C11 N12 99.4(9) . . y N15 C11 W1 146.6(8) . . y N12 C11 W1 113.9(8) . . y C13 N12 C11 117.3(9) . . ? C13 N12 C121 130.5(9) . . ? C11 N12 C121 112.2(10) . . ? C14 C13 N12 102.8(11) . . ? C13 C14 N15 109.0(11) . . ? C11 N15 C14 111.6(8) . . ? C11 N15 C151 122.5(9) . . ? C14 N15 C151 125.9(9) . . ? C126 C121 C122 124.6(9) . . ? C126 C121 N12 116.9(9) . . ? C122 C121 N12 118.0(9) . . ? C123 C122 C121 117.3(9) . . ? C123 C122 C127 117.6(9) . . ? C121 C122 C127 124.1(9) . . ? C122 C123 C124 120.5(10) . . ? C123 C124 C125 118.1(10) . . ? C123 C124 C128 120.2(11) . . ? C125 C124 C128 121.7(11) . . ? C126 C125 C124 123.8(10) . . ? C125 C126 C121 115.6(10) . . ? C125 C126 C129 122.4(10) . . ? C121 C126 C129 122.0(10) . . ? C152 C151 C156 121.5(10) . . ? C152 C151 N15 119.6(8) . . ? C156 C151 N15 118.9(9) . . ? C151 C152 C153 118.4(9) . . ? C151 C152 C157 120.6(10) . . ? C153 C152 C157 120.8(9) . . ? C154 C153 C152 122.2(9) . . ? C155 C154 C153 117.9(9) . . ? C155 C154 C158 120.5(9) . . ? C153 C154 C158 121.5(10) . . ? C154 C155 C156 122.3(9) . . ? C155 C156 C151 117.6(10) . . ? C155 C156 C159 121.3(10) . . ? C151 C156 C159 121.1(10) . . ? C61 B1 C91 111.8(7) . . ? C61 B1 C71 112.7(8) . . ? C91 B1 C71 99.3(8) . . ? C61 B1 C81 99.4(9) . . ? C91 B1 C81 116.7(8) . . ? C71 B1 C81 117.5(8) . . ? C66 C61 C62 114.8(8) . . ? C66 C61 B1 119.0(8) . . ? C62 C61 B1 125.2(8) . . ? C63 C62 F62 115.5(8) . . ? C63 C62 C61 121.3(9) . . ? F62 C62 C61 123.2(8) . . ? C62 C63 F63 118.3(9) . . ? C62 C63 C64 121.6(9) . . ? F63 C63 C64 120.1(9) . . ? F64 C64 C65 119.8(9) . . ? F64 C64 C63 121.1(9) . . ? C65 C64 C63 119.1(9) . . ? C66 C65 F65 121.9(9) . . ? C66 C65 C64 117.4(9) . . ? F65 C65 C64 120.7(9) . . ? C65 C66 F66 113.5(8) . . ? C65 C66 C61 125.6(9) . . ? F66 C66 C61 120.9(8) . . ? C76 C71 C72 114.6(9) . . ? C76 C71 B1 123.2(10) . . ? C72 C71 B1 122.0(8) . . ? F72 C72 C71 120.6(8) . . ? F72 C72 C73 112.0(9) . . ? C71 C72 C73 127.4(9) . . ? C74 C73 F73 119.9(10) . . ? C74 C73 C72 116.2(11) . . ? F73 C73 C72 123.9(9) . . ? C73 C74 F74 117.5(12) . . ? C73 C74 C75 119.4(11) . . ? F74 C74 C75 123.0(10) . . ? F75 C75 C74 120.3(10) . . ? F75 C75 C76 117.0(12) . . ? C74 C75 C76 122.7(9) . . ? F76 C76 C71 121.1(9) . . ? F76 C76 C75 119.2(9) . . ? C71 C76 C75 119.7(11) . . ? C82 C81 C86 109.1(10) . . ? C82 C81 B1 121.2(9) . . ? C86 C81 B1 129.0(9) . . ? F82 C82 C81 115.0(10) . . ? F82 C82 C83 117.9(9) . . ? C81 C82 C83 127.1(9) . . ? F83 C83 C84 117.4(11) . . ? F83 C83 C82 121.8(10) . . ? C84 C83 C82 120.8(10) . . ? C85 C84 C83 115.7(12) . . ? C85 C84 F84 121.8(11) . . ? C83 C84 F84 122.4(11) . . ? F85 C85 C84 116.1(12) . . ? F85 C85 C86 122.6(10) . . ? C84 C85 C86 121.3(10) . . ? F86 C86 C81 117.8(10) . . ? F86 C86 C85 116.2(9) . . ? C81 C86 C85 125.9(10) . . ? C96 C91 C92 112.4(10) . . ? C96 C91 B1 118.2(9) . . ? C92 C91 B1 129.2(9) . . ? F92 C92 C93 113.6(9) . . ? F92 C92 C91 121.4(9) . . ? C93 C92 C91 125.0(10) . . ? C94 C93 F93 119.4(10) . . ? C94 C93 C92 119.3(11) . . ? F93 C93 C92 121.3(10) . . ? C93 C94 F94 119.9(12) . . ? C93 C94 C95 119.4(11) . . ? F94 C94 C95 120.7(12) . . ? F95 C95 C96 117.5(11) . . ? F95 C95 C94 122.0(11) . . ? C96 C95 C94 120.6(11) . . ? C91 C96 C95 123.3(11) . . ? C91 C96 F96 117.5(9) . . ? C95 C96 F96 119.2(9) . . ? C332 C331 C335 171(5) . . ? C332 C331 C333 139(3) . . ? C335 C331 C333 50(4) . . ? C332 C331 C333 47(3) . 3_566 ? C335 C331 C333 141(4) . 3_566 ? C333 C331 C333 91(2) . 3_566 ? C331 C332 C333 91(4) . 3_566 ? C331 C332 C334 128(5) . . ? C333 C332 C334 37(4) 3_566 . ? C334 C333 C332 98(7) 3_566 3_566 ? C334 C333 C335 88(8) 3_566 . ? C332 C333 C335 172(4) 3_566 . ? C334 C333 C331 131(7) 3_566 . ? C332 C333 C331 130(4) 3_566 . ? C335 C333 C331 44(3) . . ? C334 C333 C331 140(7) 3_566 3_566 ? C332 C333 C331 42(2) 3_566 3_566 ? C335 C333 C331 132(4) . 3_566 ? C331 C333 C331 89(2) . 3_566 ? C333 C334 C335 51(4) 3_566 3_566 ? C333 C334 C332 44(4) 3_566 . ? C335 C334 C332 95(3) 3_566 . ? C331 C335 C333 86(5) . . ? C331 C335 C334 127(7) . 3_566 ? C333 C335 C334 41(4) . 3_566 ? _diffrn_measured_fraction_theta_max 0.761 _diffrn_reflns_theta_full 28.25 _diffrn_measured_fraction_theta_full 0.761 _refine_diff_density_max 2.775 _refine_diff_density_min -0.998 _refine_diff_density_rms 0.118