# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_pt76a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H33 B O2' _chemical_formula_sum 'C29 H33 B O2' _chemical_formula_weight 424.36 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' C C 0.0033 0.0016 '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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 13.3757(8) _cell_length_b 11.6597(6) _cell_length_c 16.4980(9) _cell_angle_alpha 90.00 _cell_angle_beta 109.092(3) _cell_angle_gamma 90.00 _cell_volume 2431.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7669 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 29.95 _exptl_crystal_description RECTANGULAR _exptl_crystal_colour COLOURLESS _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.159 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912.0 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.967 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 53300 _diffrn_reflns_av_R_equivalents 0.0646 _diffrn_reflns_av_sigmaI/netI 0.0545 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 30.55 _reflns_number_total 7441 _reflns_number_gt 4846 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0533P)^2^+0.6273P] 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 7441 _refine_ls_number_parameters 421 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0940 _refine_ls_R_factor_gt 0.0515 _refine_ls_wR_factor_ref 0.1317 _refine_ls_wR_factor_gt 0.1124 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.039 _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 O1 O 0.84118(9) 0.13869(11) 1.07734(7) 0.0474(4) Uani 1 1 d D . . O2 O 0.91442(8) 0.22366(11) 0.97069(8) 0.0473(3) Uani 1 1 d . . . C22 C 0.16836(9) 0.36204(11) 0.62125(8) 0.0179(3) Uani 1 1 d . . . C8 C 0.22392(9) 0.28254(11) 0.68455(8) 0.0169(3) Uani 1 1 d . . . C26 C 0.19923(10) 0.27850(12) 0.76168(8) 0.0199(3) Uani 1 1 d . . . C9 C 0.42235(10) 0.19631(11) 0.74303(8) 0.0183(3) Uani 1 1 d . . . C18 C 0.20742(10) 0.05341(11) 0.55785(8) 0.0177(3) Uani 1 1 d . . . C23 C 0.09741(10) 0.43848(12) 0.63766(9) 0.0218(3) Uani 1 1 d . . . C14 C 0.36839(10) 0.13042(12) 0.54250(8) 0.0198(3) Uani 1 1 d . . . C7 C 0.29486(9) 0.12810(11) 0.58805(8) 0.0165(3) Uani 1 1 d . . . C17 C 0.19830(10) -0.01950(12) 0.48857(8) 0.0198(3) Uani 1 1 d . . . C6 C 0.62487(10) 0.18722(12) 0.87038(8) 0.0216(3) Uani 1 1 d . . . C25 C 0.12409(10) 0.35301(13) 0.77384(9) 0.0248(3) Uani 1 1 d . . . C21 C 0.12070(11) 0.05109(13) 0.59792(10) 0.0231(3) Uani 1 1 d . . . C16 C 0.27227(10) -0.01910(12) 0.44601(8) 0.0211(3) Uani 1 1 d . . . C11 C 0.56434(10) 0.28710(12) 0.85758(8) 0.0196(3) Uani 1 1 d . . . C12 C 0.58339(11) 0.09200(13) 0.81957(9) 0.0273(3) Uani 1 1 d . . . C24 C 0.07436(10) 0.43543(13) 0.71390(9) 0.0250(3) Uani 1 1 d . . . C29 C 0.18211(11) 0.36651(13) 0.53408(9) 0.0227(3) Uani 1 1 d . . . C15 C 0.35571(10) 0.05773(12) 0.47315(8) 0.0214(3) Uani 1 1 d . . . C2 C 0.82350(11) 0.22421(14) 0.91603(11) 0.0345(4) Uani 1 1 d . . . C3 C 0.73266(11) 0.18342(13) 0.93706(9) 0.0271(3) Uani 1 1 d . . . C4 C 0.74646(12) 0.14077(14) 1.01698(10) 0.0337(4) Uani 1 1 d D . . C27 C 0.24866(12) 0.19153(14) 0.83120(9) 0.0259(3) Uani 1 1 d . . . C10 C 0.46449(10) 0.29044(11) 0.79608(8) 0.0182(3) Uani 1 1 d . . . C19 C 0.45711(12) 0.21687(15) 0.56303(11) 0.0300(3) Uani 1 1 d . . . C13 C 0.48469(11) 0.09708(12) 0.75663(9) 0.0249(3) Uani 1 1 d . . . C20 C 0.26161(14) -0.09839(14) 0.37180(10) 0.0293(3) Uani 1 1 d . . . C5 C 0.66185(15) 0.09083(17) 1.04548(11) 0.0398(4) Uani 1 1 d . . . C1 C 0.80984(15) 0.26677(18) 0.82814(12) 0.0421(4) Uani 1 1 d . . . C28 C -0.00345(13) 0.51827(18) 0.72989(13) 0.0387(4) Uani 1 1 d . . . B1 B 0.31143(11) 0.20299(12) 0.67077(9) 0.0168(3) Uani 1 1 d . . . H33 H 0.1374(12) -0.0708(13) 0.4690(9) 0.023(4) Uiso 1 1 d . . . H11 H 0.5932(11) 0.3542(13) 0.8937(9) 0.021(4) Uiso 1 1 d . . . H30 H 0.0633(11) 0.4968(13) 0.5946(9) 0.022(4) Uiso 1 1 d . . . H10 H 0.4221(11) 0.3599(13) 0.7877(9) 0.023(4) Uiso 1 1 d . . . H8 H 0.6259(12) 0.0212(15) 0.8277(10) 0.033(4) Uiso 1 1 d . . . H31 H 0.1066(12) 0.3461(13) 0.8270(10) 0.029(4) Uiso 1 1 d . . . H32 H 0.4064(12) 0.0621(13) 0.4405(10) 0.029(4) Uiso 1 1 d . . . H2 H 0.8815(17) 0.2877(17) 0.8232(13) 0.059(6) Uiso 1 1 d . . . H26 H -0.0017(17) 0.593(2) 0.7015(14) 0.074(7) Uiso 1 1 d . . . H6 H 0.5901(15) 0.0989(16) 1.0042(12) 0.047(5) Uiso 1 1 d . . . H15 H 0.3141(17) -0.159(2) 0.3854(13) 0.067(6) Uiso 1 1 d . . . H16 H 0.2669(15) -0.0579(18) 0.3225(13) 0.056(6) Uiso 1 1 d . . . H5 H 0.6710(16) 0.009(2) 1.0551(13) 0.061(6) Uiso 1 1 d . . . H4 H 0.7643(16) 0.3341(19) 0.8156(13) 0.059(6) Uiso 1 1 d . . . H17 H 0.1924(17) -0.1372(18) 0.3527(13) 0.062(6) Uiso 1 1 d . . . H25 H 0.0120(15) 0.5366(18) 0.7920(14) 0.062(6) Uiso 1 1 d . . . H3 H 0.7758(16) 0.2087(18) 0.7867(13) 0.060(6) Uiso 1 1 d . . . H7 H 0.6630(16) 0.1264(18) 1.1004(14) 0.063(6) Uiso 1 1 d . . . H9 H 0.4560(12) 0.0295(14) 0.7204(10) 0.028(4) Uiso 1 1 d . . . H14 H 0.4947(13) 0.2163(14) 0.5200(11) 0.038(5) Uiso 1 1 d . . . H23 H 0.3167(15) 0.2196(15) 0.8711(12) 0.045(5) Uiso 1 1 d . . . H21 H 0.2640(13) 0.1188(16) 0.8071(11) 0.043(5) Uiso 1 1 d . . . H22 H 0.2008(15) 0.1749(16) 0.8640(12) 0.049(5) Uiso 1 1 d . . . H13 H 0.5108(17) 0.2033(17) 0.6184(14) 0.062(6) Uiso 1 1 d . . . H24 H -0.0754(18) 0.4835(19) 0.7097(13) 0.066(6) Uiso 1 1 d . . . H12 H 0.4310(16) 0.2968(19) 0.5651(13) 0.065(6) Uiso 1 1 d . . . H19 H 0.0751(12) -0.0161(14) 0.5792(9) 0.026(4) Uiso 1 1 d . . . H29 H 0.1467(12) 0.4354(14) 0.5019(10) 0.031(4) Uiso 1 1 d . . . H20 H 0.0757(14) 0.1223(16) 0.5815(11) 0.040(5) Uiso 1 1 d . . . H18 H 0.1503(13) 0.0465(14) 0.6630(11) 0.034(4) Uiso 1 1 d . . . H28 H 0.2564(13) 0.3705(14) 0.5371(10) 0.033(4) Uiso 1 1 d . . . H27 H 0.1496(14) 0.2983(15) 0.4991(11) 0.040(5) Uiso 1 1 d . . . H1 H 0.9008(18) 0.177(2) 1.0425(17) 0.124(11) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0402(7) 0.0509(8) 0.0301(6) -0.0114(6) -0.0168(5) 0.0247(6) O2 0.0203(5) 0.0490(8) 0.0591(8) -0.0265(6) -0.0055(5) 0.0065(5) C22 0.0149(6) 0.0201(7) 0.0175(6) -0.0014(5) 0.0036(5) -0.0031(5) C8 0.0145(6) 0.0189(6) 0.0157(6) -0.0021(5) 0.0029(5) -0.0036(5) C26 0.0171(6) 0.0257(7) 0.0151(6) -0.0041(5) 0.0031(5) -0.0066(5) C9 0.0176(6) 0.0187(7) 0.0166(6) -0.0008(5) 0.0027(5) 0.0004(5) C18 0.0156(6) 0.0194(7) 0.0157(6) 0.0025(5) 0.0019(5) 0.0014(5) C23 0.0159(6) 0.0220(7) 0.0237(7) -0.0030(6) 0.0016(5) 0.0003(5) C14 0.0161(6) 0.0229(7) 0.0191(6) 0.0018(5) 0.0041(5) 0.0015(5) C7 0.0143(6) 0.0186(6) 0.0148(6) 0.0022(5) 0.0023(4) 0.0023(5) C17 0.0194(6) 0.0187(7) 0.0175(6) 0.0011(5) 0.0011(5) 0.0011(5) C6 0.0187(6) 0.0238(7) 0.0178(6) -0.0024(5) -0.0002(5) 0.0033(5) C25 0.0195(6) 0.0367(8) 0.0195(7) -0.0093(6) 0.0084(5) -0.0072(6) C21 0.0202(7) 0.0253(8) 0.0251(7) -0.0038(6) 0.0090(6) -0.0069(6) C16 0.0242(7) 0.0215(7) 0.0150(6) 0.0017(5) 0.0027(5) 0.0080(5) C11 0.0189(6) 0.0192(7) 0.0180(6) -0.0025(5) 0.0024(5) -0.0010(5) C12 0.0258(7) 0.0217(7) 0.0264(7) -0.0038(6) -0.0024(6) 0.0082(6) C24 0.0143(6) 0.0312(8) 0.0283(7) -0.0115(6) 0.0051(5) -0.0019(5) C29 0.0233(7) 0.0251(8) 0.0195(7) 0.0049(6) 0.0069(5) 0.0037(6) C15 0.0209(6) 0.0258(7) 0.0185(7) 0.0027(5) 0.0076(5) 0.0055(5) C2 0.0217(7) 0.0320(9) 0.0427(9) -0.0210(7) 0.0010(6) 0.0052(6) C3 0.0218(7) 0.0255(7) 0.0257(7) -0.0090(6) -0.0034(6) 0.0085(6) C4 0.0309(8) 0.0323(9) 0.0267(8) -0.0079(6) -0.0058(6) 0.0173(7) C27 0.0275(7) 0.0326(9) 0.0171(7) 0.0020(6) 0.0067(6) -0.0061(6) C10 0.0173(6) 0.0168(6) 0.0191(6) 0.0005(5) 0.0041(5) 0.0025(5) C19 0.0211(7) 0.0384(10) 0.0343(9) -0.0051(7) 0.0142(7) -0.0072(6) C13 0.0248(7) 0.0195(7) 0.0237(7) -0.0055(6) -0.0015(5) 0.0027(6) C20 0.0343(9) 0.0296(8) 0.0222(8) -0.0043(6) 0.0067(6) 0.0088(7) C5 0.0501(11) 0.0367(10) 0.0263(9) 0.0016(7) 0.0041(8) 0.0196(8) C1 0.0343(9) 0.0481(12) 0.0460(11) -0.0208(9) 0.0160(8) -0.0100(9) C28 0.0233(8) 0.0489(11) 0.0442(11) -0.0191(9) 0.0113(7) 0.0048(7) B1 0.0175(7) 0.0160(7) 0.0165(7) 0.0033(5) 0.0051(5) -0.0027(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C4 1.3312(17) . ? O2 C2 1.2549(17) . ? C22 C23 1.3915(18) . ? C22 C8 1.4122(18) . ? C22 C29 1.5091(18) . ? C8 C26 1.4162(18) . ? C8 B1 1.5673(19) . ? C26 C25 1.3917(19) . ? C26 C27 1.511(2) . ? C9 C13 1.4006(19) . ? C9 C10 1.4020(18) . ? C9 B1 1.5721(19) . ? C18 C17 1.3974(18) . ? C18 C7 1.4119(18) . ? C18 C21 1.5115(18) . ? C23 C24 1.390(2) . ? C14 C15 1.3889(19) . ? C14 C7 1.4200(17) . ? C14 C19 1.509(2) . ? C7 B1 1.5734(19) . ? C17 C16 1.3881(18) . ? C6 C12 1.393(2) . ? C6 C11 1.3944(18) . ? C6 C3 1.5011(18) . ? C25 C24 1.383(2) . ? C16 C15 1.386(2) . ? C16 C20 1.503(2) . ? C11 C10 1.3887(18) . ? C12 C13 1.3885(19) . ? C24 C28 1.505(2) . ? C2 C3 1.449(2) . ? C2 C1 1.486(3) . ? C3 C4 1.364(2) . ? C4 C5 1.480(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C23 C22 C8 120.26(12) . . ? C23 C22 C29 117.82(12) . . ? C8 C22 C29 121.92(11) . . ? C22 C8 C26 117.74(11) . . ? C22 C8 B1 121.23(11) . . ? C26 C8 B1 121.02(11) . . ? C25 C26 C8 120.02(12) . . ? C25 C26 C27 117.82(12) . . ? C8 C26 C27 122.10(12) . . ? C13 C9 C10 116.74(12) . . ? C13 C9 B1 121.81(12) . . ? C10 C9 B1 121.44(11) . . ? C17 C18 C7 120.30(11) . . ? C17 C18 C21 118.21(12) . . ? C7 C18 C21 121.48(12) . . ? C24 C23 C22 121.80(13) . . ? C15 C14 C7 120.35(12) . . ? C15 C14 C19 117.89(12) . . ? C7 C14 C19 121.60(12) . . ? C18 C7 C14 117.52(11) . . ? C18 C7 B1 120.92(11) . . ? C14 C7 B1 121.53(11) . . ? C16 C17 C18 121.72(13) . . ? C12 C6 C11 118.52(12) . . ? C12 C6 C3 121.04(12) . . ? C11 C6 C3 120.44(12) . . ? C24 C25 C26 122.12(13) . . ? C15 C16 C17 118.07(12) . . ? C15 C16 C20 120.83(13) . . ? C17 C16 C20 121.10(13) . . ? C10 C11 C6 120.41(12) . . ? C13 C12 C6 120.68(13) . . ? C25 C24 C23 117.88(12) . . ? C25 C24 C28 121.26(14) . . ? C23 C24 C28 120.86(15) . . ? C16 C15 C14 121.93(12) . . ? O2 C2 C3 121.19(16) . . ? O2 C2 C1 118.93(16) . . ? C3 C2 C1 119.88(13) . . ? C4 C3 C2 119.49(13) . . ? C4 C3 C6 120.86(14) . . ? C2 C3 C6 119.64(13) . . ? O1 C4 C3 121.63(16) . . ? O1 C4 C5 113.26(15) . . ? C3 C4 C5 125.10(14) . . ? C11 C10 C9 121.89(12) . . ? C12 C13 C9 121.72(13) . . ? C8 B1 C9 118.93(11) . . ? C8 B1 C7 123.66(11) . . ? C9 B1 C7 117.42(11) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.55 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.318 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.050 _database_code_depnum_ccdc_archive 'CCDC 963972' ####################################################################### # # 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_ptrj_m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H32 B2 F2 O2, C6 H12' _chemical_formula_sum 'C35 H44 B2 F2 O2' _chemical_formula_weight 556.32 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.714(2) _cell_length_b 15.194(4) _cell_length_c 23.608(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3125.9(13) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 7869 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 27.92 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.182 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.992 _exptl_absorpt_correction_T_max 0.992 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29013 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_sigmaI/netI 0.0158 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5503 _reflns_number_gt 5325 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1310P)^2^+2.1075P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.5(11) _refine_ls_number_reflns 5503 _refine_ls_number_parameters 348 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0683 _refine_ls_R_factor_gt 0.0666 _refine_ls_wR_factor_ref 0.1972 _refine_ls_wR_factor_gt 0.1949 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.060 _refine_ls_shift/su_mean 0.002 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 O2 O 0.0809(2) 0.19515(13) -0.00336(8) 0.0301(4) Uani 1 1 d . . . O1 O -0.0568(2) 0.33453(13) 0.00048(8) 0.0286(4) Uani 1 1 d . . . F1 F 0.1741(2) 0.32003(13) -0.04917(8) 0.0469(5) Uani 1 1 d . . . C4 C 0.0789(3) 0.19260(19) 0.05136(11) 0.0270(6) Uani 1 1 d . . . C3 C 0.0171(3) 0.26061(19) 0.08369(11) 0.0261(6) Uani 1 1 d . . . C7 C 0.0247(3) 0.24246(19) 0.26667(12) 0.0310(6) Uani 1 1 d . . . C6 C 0.0188(3) 0.25466(19) 0.14732(12) 0.0286(6) Uani 1 1 d . . . C2 C -0.0585(3) 0.32889(19) 0.05531(11) 0.0271(6) Uani 1 1 d . . . C14 C -0.1781(4) 0.1970(2) 0.40992(12) 0.0352(7) Uani 1 1 d . . . C23 C 0.3719(4) 0.3034(2) 0.43002(14) 0.0385(7) Uani 1 1 d . . . H25 H 0.4471 0.2759 0.4516 0.046 Uiso 1 1 calc R . . C8 C 0.1506(4) 0.29133(19) 0.36706(11) 0.0314(6) Uani 1 1 d . . . C10 C -0.1097(4) 0.2230(2) 0.23577(12) 0.0349(7) Uani 1 1 d . . . H9 H -0.1972 0.2048 0.2550 0.042 Uiso 1 1 calc R . . F2 F -0.0408(3) 0.25298(15) -0.08248(7) 0.0534(6) Uani 1 1 d . . . B1 B 0.0299(4) 0.2342(2) 0.33348(14) 0.0323(7) Uani 1 1 d . . . C22 C 0.2647(3) 0.2520(2) 0.40119(11) 0.0315(6) Uani 1 1 d . . . C13 C 0.1540(4) 0.2678(2) 0.23595(12) 0.0334(6) Uani 1 1 d . . . H10 H 0.2438 0.2814 0.2554 0.040 Uiso 1 1 calc R . . C1 C -0.1513(3) 0.39799(19) 0.08359(13) 0.0331(6) Uani 1 1 d . . . H2 H -0.1172 0.4550 0.0713 0.050 Uiso 1 1 calc R . . H1 H -0.1393 0.3932 0.1239 0.050 Uiso 1 1 calc R . . H3 H -0.2574 0.3905 0.0738 0.050 Uiso 1 1 calc R . . C24 C 0.3691(4) 0.3944(2) 0.42735(14) 0.0388(7) Uani 1 1 d . . . C9 C -0.0834(4) 0.1689(2) 0.36443(11) 0.0316(6) Uani 1 1 d . . . C12 C 0.1527(3) 0.2733(2) 0.17724(12) 0.0311(6) Uani 1 1 d . . . H7 H 0.2413 0.2894 0.1579 0.037 Uiso 1 1 calc R . . C5 C 0.1387(4) 0.1098(2) 0.07656(13) 0.0351(7) Uani 1 1 d . . . H6 H 0.0816 0.0961 0.1102 0.053 Uiso 1 1 calc R . . H4 H 0.2450 0.1172 0.0860 0.053 Uiso 1 1 calc R . . H5 H 0.1281 0.0627 0.0497 0.053 Uiso 1 1 calc R . . C18 C -0.0914(4) 0.0791(2) 0.34887(12) 0.0365(7) Uani 1 1 d . . . C11 C -0.1137(3) 0.2307(2) 0.17692(12) 0.0345(7) Uani 1 1 d . . . H8 H -0.2045 0.2198 0.1574 0.041 Uiso 1 1 calc R . . C26 C 0.1504(4) 0.3842(2) 0.36345(12) 0.0378(7) Uani 1 1 d . . . C17 C -0.1871(4) 0.0212(2) 0.37809(14) 0.0411(8) Uani 1 1 d . . . H14 H -0.1883 -0.0379 0.3678 0.049 Uiso 1 1 calc R . . C25 C 0.2570(4) 0.4334(2) 0.39434(13) 0.0414(8) Uani 1 1 d . . . H26 H 0.2524 0.4945 0.3926 0.050 Uiso 1 1 calc R . . C15 C -0.2756(4) 0.1378(3) 0.43711(14) 0.0431(8) Uani 1 1 d . . . H15 H -0.3386 0.1583 0.4660 0.052 Uiso 1 1 calc R . . C27 C 0.2771(4) 0.1528(2) 0.40684(15) 0.0412(8) Uani 1 1 d . . . H24 H 0.3667 0.1382 0.4285 0.062 Uiso 1 1 calc R . . H22 H 0.2848 0.1268 0.3699 0.062 Uiso 1 1 calc R . . H23 H 0.1875 0.1305 0.4257 0.062 Uiso 1 1 calc R . . B2 B 0.0410(4) 0.2763(2) -0.03573(13) 0.0322(7) Uani 1 1 d . . . C21 C 0.0080(6) 0.0409(2) 0.30263(14) 0.0535(10) Uani 1 1 d . . . H13 H 0.0014 -0.0221 0.3035 0.080 Uiso 1 1 calc R . . H11 H 0.1125 0.0586 0.3085 0.080 Uiso 1 1 calc R . . H12 H -0.0268 0.0620 0.2665 0.080 Uiso 1 1 calc R . . C16 C -0.2821(4) 0.0498(2) 0.42273(15) 0.0433(8) Uani 1 1 d . . . C20 C -0.3819(5) -0.0157(3) 0.45425(19) 0.0608(11) Uani 1 1 d . . . H18 H -0.4593 0.0153 0.4752 0.091 Uiso 1 1 calc R . . H16 H -0.3196 -0.0492 0.4799 0.091 Uiso 1 1 calc R . . H17 H -0.4299 -0.0547 0.4276 0.091 Uiso 1 1 calc R . . C28 C 0.4857(5) 0.4484(2) 0.46070(19) 0.0543(10) Uani 1 1 d . . . H27 H 0.5065 0.4198 0.4962 0.081 Uiso 1 1 calc R . . H28 H 0.4449 0.5061 0.4677 0.081 Uiso 1 1 calc R . . H29 H 0.5789 0.4532 0.4393 0.081 Uiso 1 1 calc R . . C19 C -0.1811(5) 0.2916(2) 0.42922(15) 0.0456(8) Uani 1 1 d . . . H20 H -0.2413 0.2964 0.4631 0.068 Uiso 1 1 calc R . . H19 H -0.2257 0.3276 0.4001 0.068 Uiso 1 1 calc R . . H21 H -0.0783 0.3111 0.4367 0.068 Uiso 1 1 calc R . . C29 C 0.0300(6) 0.4331(2) 0.32983(17) 0.0630(12) Uani 1 1 d . . . H30 H -0.0688 0.4242 0.3469 0.094 Uiso 1 1 calc R . . H32 H 0.0285 0.4114 0.2916 0.094 Uiso 1 1 calc R . . H31 H 0.0538 0.4948 0.3296 0.094 Uiso 1 1 calc R . . C30 C 0.4442(12) 0.8624(7) 0.2160(4) 0.149(3) Uiso 1 1 d . . . H34 H 0.3740 0.8538 0.1851 0.224 Uiso 1 1 calc R . . H35 H 0.4367 0.8137 0.2418 0.224 Uiso 1 1 calc R . . H33 H 0.5470 0.8661 0.2015 0.224 Uiso 1 1 calc R . . C31 C 0.406(2) 0.9445(11) 0.2458(6) 0.219(6) Uiso 1 1 d . . . H36 H 0.2996 0.9348 0.2581 0.263 Uiso 1 1 calc R . . C34 C 0.5070(10) 1.0917(6) 0.2123(4) 0.125(3) Uiso 1 1 d . . . H42 H 0.6089 1.0780 0.1983 0.150 Uiso 1 1 calc R . . H41 H 0.4741 1.1484 0.1977 0.150 Uiso 1 1 calc R . . C33 C 0.4971(11) 1.0868(6) 0.2735(4) 0.133(3) Uiso 1 1 d . . . H39 H 0.4119 1.1222 0.2870 0.160 Uiso 1 1 calc R . . H40 H 0.5908 1.1089 0.2905 0.160 Uiso 1 1 calc R . . C32 C 0.4709(12) 0.9821(6) 0.2911(4) 0.134(3) Uiso 1 1 d . . . H38 H 0.5682 0.9542 0.2998 0.161 Uiso 1 1 calc R . . H37 H 0.4044 0.9774 0.3239 0.161 Uiso 1 1 calc R . . C36 C 0.3897(13) 1.0176(7) 0.1997(4) 0.146(3) Uiso 1 1 d . . . H43 H 0.4091 0.9929 0.1625 0.175 Uiso 1 1 calc R . . H44 H 0.2864 1.0413 0.2001 0.175 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 O2 0.0343(10) 0.0361(10) 0.0199(9) -0.0035(8) 0.0001(8) 0.0020(8) O1 0.0298(10) 0.0360(10) 0.0200(9) 0.0040(8) 0.0010(8) 0.0026(8) F1 0.0449(11) 0.0509(11) 0.0449(11) 0.0119(9) 0.0207(9) 0.0065(9) C4 0.0243(13) 0.0340(14) 0.0227(13) 0.0012(11) -0.0013(10) -0.0064(11) C3 0.0230(13) 0.0341(14) 0.0210(14) 0.0006(11) 0.0009(10) -0.0026(11) C7 0.0379(16) 0.0339(14) 0.0211(14) -0.0003(11) -0.0012(11) 0.0015(13) C6 0.0322(14) 0.0337(14) 0.0200(13) 0.0006(11) -0.0006(11) -0.0013(12) C2 0.0252(13) 0.0320(13) 0.0242(13) -0.0013(11) -0.0015(10) -0.0057(11) C14 0.0369(16) 0.0426(16) 0.0262(14) 0.0034(12) -0.0020(12) 0.0053(13) C23 0.0356(17) 0.0395(16) 0.0403(17) -0.0070(13) 0.0005(13) -0.0008(13) C8 0.0465(16) 0.0316(14) 0.0162(12) -0.0010(11) 0.0035(12) -0.0022(13) C10 0.0297(15) 0.0502(17) 0.0249(14) 0.0033(12) 0.0039(11) -0.0041(13) F2 0.0742(14) 0.0623(13) 0.0235(9) -0.0083(9) -0.0155(9) 0.0218(12) B1 0.0446(19) 0.0315(16) 0.0208(15) -0.0023(12) 0.0007(13) 0.0085(14) C22 0.0383(15) 0.0318(15) 0.0245(14) -0.0031(11) 0.0015(12) -0.0024(13) C13 0.0344(15) 0.0423(16) 0.0234(13) -0.0037(12) -0.0040(12) -0.0028(13) C1 0.0333(14) 0.0364(15) 0.0296(14) -0.0017(12) -0.0016(12) 0.0027(12) C24 0.0367(17) 0.0380(16) 0.0418(17) -0.0092(13) 0.0102(14) -0.0089(13) C9 0.0373(15) 0.0391(15) 0.0183(12) -0.0001(11) -0.0077(11) 0.0000(13) C12 0.0320(14) 0.0388(15) 0.0224(13) 0.0008(11) -0.0002(12) -0.0043(12) C5 0.0416(17) 0.0359(15) 0.0280(14) 0.0020(12) 0.0034(13) 0.0030(13) C18 0.0482(19) 0.0378(15) 0.0234(13) -0.0016(12) -0.0090(13) -0.0022(14) C11 0.0267(14) 0.0513(18) 0.0255(14) 0.0042(12) -0.0039(11) -0.0033(13) C26 0.060(2) 0.0320(15) 0.0212(13) 0.0011(11) 0.0036(14) 0.0025(14) C17 0.0496(19) 0.0368(16) 0.0368(17) 0.0021(13) -0.0136(14) -0.0077(14) C25 0.062(2) 0.0279(15) 0.0346(16) -0.0012(12) 0.0121(16) -0.0064(15) C15 0.0327(16) 0.059(2) 0.0375(17) 0.0071(14) 0.0043(13) 0.0055(15) C27 0.0416(17) 0.0342(16) 0.0479(19) -0.0030(14) -0.0108(14) 0.0026(14) B2 0.0360(17) 0.0415(18) 0.0193(14) 0.0011(12) 0.0016(13) 0.0070(14) C21 0.094(3) 0.0377(17) 0.0284(16) -0.0061(13) 0.0000(18) -0.0006(19) C16 0.0309(16) 0.0518(19) 0.0472(19) 0.0119(15) -0.0066(14) -0.0053(14) C20 0.042(2) 0.072(3) 0.068(3) 0.024(2) 0.0005(18) -0.0126(19) C28 0.046(2) 0.0418(19) 0.075(3) -0.0175(18) 0.0006(19) -0.0102(16) C19 0.057(2) 0.0450(18) 0.0350(17) -0.0041(14) 0.0109(16) 0.0097(16) C29 0.109(4) 0.0357(18) 0.045(2) 0.0033(15) -0.030(2) 0.008(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 O2 C4 1.293(3) . ? O2 B2 1.492(4) . ? O1 C2 1.297(3) . ? O1 B2 1.496(4) . ? F1 B2 1.374(4) . ? C4 C3 1.393(4) . ? C4 C5 1.486(4) . ? C3 C2 1.400(4) . ? C3 C6 1.505(4) . ? C7 C13 1.394(4) . ? C7 C10 1.411(4) . ? C7 B1 1.583(4) . ? C6 C12 1.393(4) . ? C6 C11 1.398(4) . ? C2 C1 1.484(4) . ? C14 C15 1.394(5) . ? C14 C9 1.420(4) . ? C14 C19 1.509(5) . ? C23 C24 1.384(5) . ? C23 C22 1.395(4) . ? C8 C22 1.413(4) . ? C8 C26 1.413(4) . ? C8 B1 1.577(5) . ? C10 C11 1.395(4) . ? F2 B2 1.361(4) . ? B1 C9 1.579(5) . ? C22 C27 1.517(4) . ? C13 C12 1.389(4) . ? C24 C25 1.383(5) . ? C24 C28 1.524(5) . ? C9 C18 1.415(4) . ? C18 C17 1.395(5) . ? C18 C21 1.509(5) . ? C26 C25 1.398(5) . ? C26 C29 1.511(5) . ? C17 C16 1.408(5) . ? C15 C16 1.381(5) . ? C16 C20 1.517(5) . ? C30 C31 1.471(16) . ? C31 C32 1.339(15) . ? C31 C36 1.561(16) . ? C34 C33 1.450(10) . ? C34 C36 1.550(12) . ? C33 C32 1.660(13) . ? 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 C4 O2 B2 122.2(2) . . ? C2 O1 B2 122.5(2) . . ? O2 C4 C3 122.1(3) . . ? O2 C4 C5 114.9(2) . . ? C3 C4 C5 123.0(2) . . ? C4 C3 C2 118.0(2) . . ? C4 C3 C6 119.9(2) . . ? C2 C3 C6 121.8(2) . . ? C13 C7 C10 117.4(2) . . ? C13 C7 B1 121.2(3) . . ? C10 C7 B1 121.5(3) . . ? C12 C6 C11 119.4(3) . . ? C12 C6 C3 120.1(2) . . ? C11 C6 C3 120.4(2) . . ? O1 C2 C3 121.4(3) . . ? O1 C2 C1 114.1(2) . . ? C3 C2 C1 124.4(2) . . ? C15 C14 C9 120.6(3) . . ? C15 C14 C19 117.7(3) . . ? C9 C14 C19 121.6(3) . . ? C24 C23 C22 121.7(3) . . ? C22 C8 C26 117.3(3) . . ? C22 C8 B1 121.6(3) . . ? C26 C8 B1 121.2(3) . . ? C11 C10 C7 121.2(3) . . ? C8 B1 C9 122.0(2) . . ? C8 B1 C7 118.4(3) . . ? C9 B1 C7 119.5(3) . . ? C23 C22 C8 120.8(3) . . ? C23 C22 C27 117.8(3) . . ? C8 C22 C27 121.4(3) . . ? C12 C13 C7 122.0(3) . . ? C25 C24 C23 117.7(3) . . ? C25 C24 C28 122.1(3) . . ? C23 C24 C28 120.1(3) . . ? C18 C9 C14 117.2(3) . . ? C18 C9 B1 121.1(3) . . ? C14 C9 B1 121.7(3) . . ? C13 C12 C6 120.0(3) . . ? C17 C18 C9 120.6(3) . . ? C17 C18 C21 117.3(3) . . ? C9 C18 C21 122.0(3) . . ? C10 C11 C6 119.9(3) . . ? C25 C26 C8 120.1(3) . . ? C25 C26 C29 118.2(3) . . ? C8 C26 C29 121.6(3) . . ? C18 C17 C16 121.8(3) . . ? C24 C25 C26 122.3(3) . . ? C16 C15 C14 122.5(3) . . ? F2 B2 F1 112.4(3) . . ? F2 B2 O2 108.8(3) . . ? F1 B2 O2 108.7(3) . . ? F2 B2 O1 108.6(3) . . ? F1 B2 O1 109.1(3) . . ? O2 B2 O1 109.2(2) . . ? C15 C16 C17 117.3(3) . . ? C15 C16 C20 122.6(4) . . ? C17 C16 C20 120.1(3) . . ? C32 C31 C30 130.4(14) . . ? C32 C31 C36 106.9(12) . . ? C30 C31 C36 106.8(10) . . ? C33 C34 C36 96.5(7) . . ? C34 C33 C32 107.9(7) . . ? C31 C32 C33 105.5(10) . . ? C34 C36 C31 109.0(10) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.675 _refine_diff_density_min -0.490 _refine_diff_density_rms 0.070 _database_code_depnum_ccdc_archive 'CCDC 963973' ####################################################################### # # 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_ptb2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C33 H40 B2 F2 O2' _chemical_formula_sum 'C33 H40 B2 F2 O2' _chemical_formula_weight 528.27 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _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 42.366(14) _cell_length_b 8.600(3) _cell_length_c 15.977(5) _cell_angle_alpha 90.00 _cell_angle_beta 91.14(3) _cell_angle_gamma 90.00 _cell_volume 5820(3) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 6614 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 30.29 _exptl_crystal_description needle _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.206 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2256 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9880 _exptl_absorpt_correction_T_max 0.9904 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37629 _diffrn_reflns_av_R_equivalents 0.0918 _diffrn_reflns_av_sigmaI/netI 0.1015 _diffrn_reflns_limit_h_min -60 _diffrn_reflns_limit_h_max 60 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 31.74 _reflns_number_total 8826 _reflns_number_gt 5140 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0818P)^2^+0.5463P] 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 refU _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8826 _refine_ls_number_parameters 364 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1259 _refine_ls_R_factor_gt 0.0681 _refine_ls_wR_factor_ref 0.1693 _refine_ls_wR_factor_gt 0.1482 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.002 _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 F1 F 1.03037(3) 0.64674(13) 0.46466(8) 0.0348(3) Uani 1 1 d . . . F2 F 1.04751(3) 0.63824(13) 0.33036(8) 0.0365(3) Uani 1 1 d . . . O1 O 1.01441(3) 0.83944(14) 0.37024(10) 0.0303(3) Uani 1 1 d . . . O2 O 0.99554(3) 0.57507(14) 0.35636(9) 0.0250(3) Uani 1 1 d . . . B1 B 0.83815(4) 1.0272(2) 0.49570(13) 0.0177(4) Uani 1 1 d . . . B2 B 1.02317(5) 0.6732(3) 0.38159(16) 0.0286(5) Uani 1 1 d . . . C4 C 0.98566(4) 0.8837(2) 0.38663(13) 0.0251(4) Uani 1 1 d . . . C3 C 0.96100(4) 0.77848(19) 0.39238(12) 0.0208(4) Uani 1 1 d . . . C2 C 0.96710(4) 0.6241(2) 0.36992(12) 0.0220(4) Uani 1 1 d . . . C5 C 0.98171(5) 1.0558(2) 0.39455(17) 0.0360(5) Uani 1 1 d . . . H4 H 1.0005 1.0999 0.4193 0.054 Uiso 1 1 calc R . . H5 H 0.9640 1.0777 0.4294 0.054 Uiso 1 1 calc R . . H6 H 0.9781 1.1001 0.3401 0.054 Uiso 1 1 calc R . . C1 C 0.94195(4) 0.5066(2) 0.35604(14) 0.0277(4) Uani 1 1 d . . . H3 H 0.9442 0.4604 0.3018 0.042 Uiso 1 1 calc R . . H2 H 0.9217 0.5558 0.3591 0.042 Uiso 1 1 calc R . . H1 H 0.9437 0.4275 0.3983 0.042 Uiso 1 1 calc R . . C6 C 0.92850(4) 0.82991(18) 0.41518(12) 0.0186(3) Uani 1 1 d . . . C11 C 0.91762(4) 0.79838(18) 0.49572(11) 0.0187(3) Uani 1 1 d . . . C10 C 0.88782(4) 0.85264(18) 0.51880(11) 0.0175(3) Uani 1 1 d . . . C9 C 0.86929(4) 0.94475(17) 0.46334(11) 0.0171(3) Uani 1 1 d . . . C13 C 0.88009(4) 0.97144(18) 0.38220(11) 0.0172(3) Uani 1 1 d . . . C12 C 0.90945(4) 0.91283(18) 0.35720(11) 0.0184(3) Uani 1 1 d . . . C15 C 0.93760(4) 0.7096(2) 0.55948(12) 0.0238(4) Uani 1 1 d . . . H8 H 0.9575 0.6831 0.5354 0.036 Uiso 1 1 calc R . . H9 H 0.9268 0.6164 0.5752 0.036 Uiso 1 1 calc R . . H7 H 0.9412 0.7733 0.6081 0.036 Uiso 1 1 calc R . . C14 C 0.87578(4) 0.8088(2) 0.60360(12) 0.0226(4) Uani 1 1 d . . . H14 H 0.8724 0.6985 0.6058 0.034 Uiso 1 1 calc R . . H15 H 0.8562 0.8617 0.6131 0.034 Uiso 1 1 calc R . . H13 H 0.8910 0.8382 0.6460 0.034 Uiso 1 1 calc R . . C17 C 0.86203(4) 1.0740(2) 0.32107(12) 0.0217(4) Uani 1 1 d . . . 18 H 0.8748 1.1620 0.3068 0.033 Uiso 1 1 calc R . . H17 H 0.8429 1.1091 0.3462 0.033 Uiso 1 1 calc R . . H16 H 0.8569 1.0158 0.2713 0.033 Uiso 1 1 calc R . . C16 C 0.92016(4) 0.9428(2) 0.26930(12) 0.0249(4) Uani 1 1 d . . . H11 H 0.9039 0.9110 0.2302 0.037 Uiso 1 1 calc R . . H10 H 0.9391 0.8847 0.2593 0.037 Uiso 1 1 calc R . . H12 H 0.9243 1.0517 0.2624 0.037 Uiso 1 1 calc R . . C8 C 0.80516(4) 0.99354(18) 0.45143(11) 0.0166(3) Uani 1 1 d . . . C22 C 0.78609(4) 1.11743(18) 0.42068(11) 0.0184(3) Uani 1 1 d . . . C21 C 0.75902(4) 1.08747(19) 0.37251(12) 0.0208(4) Uani 1 1 d . . . H26 H 0.7474 1.1708 0.3511 0.025 Uiso 1 1 calc R . . C20 C 0.74877(4) 0.9370(2) 0.35537(12) 0.0212(4) Uani 1 1 d . . . C19 C 0.76634(4) 0.81546(19) 0.38970(12) 0.0216(4) Uani 1 1 d . . . H25 H 0.7594 0.7140 0.3813 0.026 Uiso 1 1 calc R . . C18 C 0.79414(4) 0.84055(18) 0.43640(12) 0.0192(3) Uani 1 1 d . . . C25 C 0.79458(4) 1.28621(18) 0.43708(13) 0.0228(4) Uani 1 1 d . . . H27 H 0.7817 1.3521 0.4020 0.034 Uiso 1 1 calc R . . H29 H 0.8164 1.3028 0.4249 0.034 Uiso 1 1 calc R . . H28 H 0.7910 1.3106 0.4948 0.034 Uiso 1 1 calc R . . C24 C 0.71982(4) 0.9090(2) 0.30113(13) 0.0277(4) Uani 1 1 d . . . H22 H 0.7196 0.8027 0.2827 0.042 Uiso 1 1 calc R . . H23 H 0.7202 0.9767 0.2534 0.042 Uiso 1 1 calc R . . H24 H 0.7013 0.9296 0.3328 0.042 Uiso 1 1 calc R . . C23 C 0.81086(4) 0.70117(19) 0.47328(13) 0.0256(4) Uani 1 1 d . . . H21 H 0.8009 0.6078 0.4530 0.038 Uiso 1 1 calc R . . H19 H 0.8098 0.7047 0.5332 0.038 Uiso 1 1 calc R . . H20 H 0.8326 0.7021 0.4571 0.038 Uiso 1 1 calc R . . C7 C 0.84191(4) 1.14499(18) 0.57116(11) 0.0173(3) Uani 1 1 d . . . C30 C 0.86672(4) 1.25489(19) 0.57643(12) 0.0207(3) Uani 1 1 d . . . C29 C 0.87016(4) 1.35067(19) 0.64596(12) 0.0221(4) Uani 1 1 d . . . H40 H 0.8865 1.4227 0.6475 0.027 Uiso 1 1 calc R . . C28 C 0.85010(4) 1.34266(19) 0.71303(12) 0.0233(4) Uani 1 1 d . . . C27 C 0.82540(4) 1.23573(19) 0.70814(12) 0.0220(4) Uani 1 1 d . . . H39 H 0.8116 1.2285 0.7525 0.026 Uiso 1 1 calc R . . C26 C 0.82078(4) 1.13951(18) 0.63902(12) 0.0195(3) Uani 1 1 d . . . C33 C 0.88997(5) 1.2782(2) 0.50701(14) 0.0316(5) Uani 1 1 d . . . H37 H 0.9013 1.3735 0.5161 0.047 Uiso 1 1 calc R . . H36 H 0.8788 1.2830 0.4542 0.047 Uiso 1 1 calc R . . H38 H 0.9046 1.1929 0.5066 0.047 Uiso 1 1 calc R . . C32 C 0.85509(5) 1.4430(2) 0.78968(14) 0.0315(4) Uani 1 1 d . . . H34 H 0.8652 1.3829 0.8332 0.047 Uiso 1 1 calc R . . H33 H 0.8351 1.4798 0.8086 0.047 Uiso 1 1 calc R . . H35 H 0.8682 1.5301 0.7760 0.047 Uiso 1 1 calc R . . C31 C 0.79348(4) 1.0263(2) 0.64121(13) 0.0254(4) Uani 1 1 d . . . H32 H 0.7848 1.0254 0.6963 0.038 Uiso 1 1 calc R . . H30 H 0.8008 0.9240 0.6275 0.038 Uiso 1 1 calc R . . H31 H 0.7775 1.0577 0.6013 0.038 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 F1 0.0290(6) 0.0382(6) 0.0371(7) 0.0018(6) -0.0020(5) 0.0035(5) F2 0.0219(5) 0.0409(6) 0.0473(8) 0.0038(6) 0.0127(5) 0.0063(5) O1 0.0179(6) 0.0283(6) 0.0450(9) 0.0039(7) 0.0067(6) 0.0009(5) O2 0.0207(6) 0.0249(6) 0.0295(7) -0.0005(6) 0.0048(5) 0.0057(5) B1 0.0189(8) 0.0143(8) 0.0201(10) 0.0030(7) 0.0035(7) -0.0018(7) B2 0.0174(9) 0.0306(10) 0.0379(14) 0.0021(10) 0.0036(9) 0.0038(8) C4 0.0190(8) 0.0254(8) 0.0310(10) 0.0002(8) 0.0029(7) 0.0020(7) C3 0.0154(7) 0.0218(8) 0.0251(10) 0.0000(7) 0.0012(7) 0.0022(6) C2 0.0197(8) 0.0249(8) 0.0214(9) 0.0016(7) 0.0027(7) 0.0042(6) C5 0.0257(10) 0.0236(9) 0.0588(15) 0.0003(10) 0.0005(9) -0.0021(7) C1 0.0234(9) 0.0233(8) 0.0364(12) -0.0035(9) 0.0023(8) 0.0005(7) C6 0.0162(7) 0.0155(7) 0.0241(9) -0.0028(7) 0.0018(6) 0.0004(6) C11 0.0175(7) 0.0166(7) 0.0219(9) -0.0014(7) -0.0019(6) -0.0007(6) C10 0.0191(8) 0.0161(7) 0.0174(8) -0.0009(7) 0.0010(6) -0.0005(6) C9 0.0161(7) 0.0146(7) 0.0208(9) -0.0022(7) 0.0012(6) -0.0020(6) C13 0.0146(7) 0.0157(7) 0.0215(9) -0.0019(7) -0.0001(6) -0.0007(6) C12 0.0174(7) 0.0170(7) 0.0208(9) -0.0013(7) 0.0023(6) -0.0008(6) C15 0.0201(8) 0.0252(8) 0.0262(10) 0.0029(8) 0.0003(7) 0.0040(7) C14 0.0235(8) 0.0230(8) 0.0213(9) 0.0015(7) 0.0024(7) 0.0033(7) C17 0.0201(8) 0.0240(8) 0.0212(9) 0.0026(7) 0.0031(7) 0.0017(7) C16 0.0228(8) 0.0292(9) 0.0229(10) 0.0022(8) 0.0040(7) 0.0039(7) C8 0.0150(7) 0.0151(7) 0.0199(9) -0.0009(7) 0.0038(6) 0.0001(6) C22 0.0178(8) 0.0161(7) 0.0214(9) 0.0008(7) 0.0044(6) 0.0000(6) C21 0.0189(8) 0.0192(7) 0.0243(10) 0.0010(7) 0.0022(7) 0.0015(6) C20 0.0175(8) 0.0242(8) 0.0222(9) -0.0005(7) 0.0032(7) -0.0021(6) C19 0.0203(8) 0.0171(7) 0.0274(10) -0.0026(7) 0.0041(7) -0.0039(6) C18 0.0179(8) 0.0155(7) 0.0243(9) -0.0010(7) 0.0032(7) -0.0002(6) C25 0.0244(8) 0.0147(7) 0.0293(10) 0.0015(7) -0.0016(7) 0.0001(6) C24 0.0230(9) 0.0290(9) 0.0311(11) -0.0002(9) -0.0029(8) -0.0035(7) C23 0.0241(9) 0.0158(7) 0.0369(11) 0.0001(8) -0.0023(8) -0.0005(6) C7 0.0152(7) 0.0155(7) 0.0211(9) -0.0010(7) 0.0012(6) 0.0016(6) C30 0.0182(8) 0.0193(7) 0.0247(9) -0.0014(7) 0.0017(7) -0.0013(6) C29 0.0195(8) 0.0187(7) 0.0280(10) -0.0020(7) -0.0028(7) -0.0014(6) C28 0.0239(9) 0.0200(8) 0.0257(10) -0.0034(8) -0.0038(7) 0.0045(7) C27 0.0221(8) 0.0231(8) 0.0208(9) -0.0009(7) 0.0052(7) 0.0026(7) C26 0.0181(8) 0.0169(7) 0.0237(9) 0.0013(7) 0.0031(7) 0.0025(6) C33 0.0290(10) 0.0323(10) 0.0340(11) -0.0084(9) 0.0094(8) -0.0151(8) C32 0.0302(10) 0.0337(10) 0.0304(11) -0.0108(9) -0.0022(8) 0.0036(8) C31 0.0245(9) 0.0241(8) 0.0280(10) -0.0036(8) 0.0104(7) -0.0038(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 B2 1.375(3) . ? F2 B2 1.363(3) . ? O1 C4 1.307(2) . ? O1 B2 1.487(3) . ? O2 C2 1.299(2) . ? O2 B2 1.492(3) . ? B1 C7 1.580(3) . ? B1 C8 1.581(3) . ? B1 C9 1.593(2) . ? C4 C3 1.387(2) . ? C4 C5 1.495(3) . ? C3 C2 1.400(2) . ? C3 C6 1.498(2) . ? C2 C1 1.482(3) . ? C6 C11 1.402(3) . ? C6 C12 1.410(2) . ? C11 C10 1.402(2) . ? C11 C15 1.517(2) . ? C10 C9 1.415(2) . ? C10 C14 1.505(3) . ? C9 C13 1.402(3) . ? C13 C12 1.407(2) . ? C13 C17 1.512(2) . ? C12 C16 1.507(3) . ? C8 C18 1.415(2) . ? C8 C22 1.419(2) . ? C22 C21 1.392(2) . ? C22 C25 1.517(2) . ? C21 C20 1.390(2) . ? C20 C19 1.390(3) . ? C20 C24 1.507(3) . ? C19 C18 1.398(2) . ? C18 C23 1.506(2) . ? C7 C30 1.415(2) . ? C7 C26 1.420(2) . ? C30 C29 1.388(3) . ? C30 C33 1.511(3) . ? C29 C28 1.383(3) . ? C28 C27 1.394(2) . ? C28 C32 1.510(3) . ? C27 C26 1.391(3) . ? C26 C31 1.513(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 O1 B2 119.11(15) . . ? C2 O2 B2 119.77(15) . . ? C7 B1 C8 122.24(14) . . ? C7 B1 C9 117.48(15) . . ? C8 B1 C9 120.26(15) . . ? F2 B2 F1 112.80(17) . . ? F2 B2 O1 109.19(17) . . ? F1 B2 O1 109.07(18) . . ? F2 B2 O2 108.17(18) . . ? F1 B2 O2 108.96(17) . . ? O1 B2 O2 108.55(15) . . ? O1 C4 C3 121.99(16) . . ? O1 C4 C5 114.29(16) . . ? C3 C4 C5 123.67(16) . . ? C4 C3 C2 117.27(15) . . ? C4 C3 C6 121.40(15) . . ? C2 C3 C6 121.16(15) . . ? O2 C2 C3 121.83(16) . . ? O2 C2 C1 114.82(15) . . ? C3 C2 C1 123.30(16) . . ? C11 C6 C12 120.43(15) . . ? C11 C6 C3 119.13(15) . . ? C12 C6 C3 120.42(16) . . ? C10 C11 C6 119.42(16) . . ? C10 C11 C15 118.95(16) . . ? C6 C11 C15 121.61(15) . . ? C11 C10 C9 120.87(16) . . ? C11 C10 C14 118.46(15) . . ? C9 C10 C14 120.67(15) . . ? C13 C9 C10 118.90(15) . . ? C13 C9 B1 120.98(15) . . ? C10 C9 B1 119.93(15) . . ? C9 C13 C12 120.69(16) . . ? C9 C13 C17 121.49(15) . . ? C12 C13 C17 117.65(16) . . ? C13 C12 C6 119.48(16) . . ? C13 C12 C16 119.19(16) . . ? C6 C12 C16 121.32(15) . . ? C18 C8 C22 117.11(15) . . ? C18 C8 B1 122.16(14) . . ? C22 C8 B1 120.64(14) . . ? C21 C22 C8 120.62(15) . . ? C21 C22 C25 117.54(15) . . ? C8 C22 C25 121.82(15) . . ? C20 C21 C22 122.11(16) . . ? C19 C20 C21 117.36(16) . . ? C19 C20 C24 122.00(16) . . ? C21 C20 C24 120.64(16) . . ? C20 C19 C18 122.23(15) . . ? C19 C18 C8 120.38(15) . . ? C19 C18 C23 118.07(14) . . ? C8 C18 C23 121.49(16) . . ? C30 C7 C26 117.10(16) . . ? C30 C7 B1 122.47(15) . . ? C26 C7 B1 120.38(14) . . ? C29 C30 C7 120.65(16) . . ? C29 C30 C33 116.69(15) . . ? C7 C30 C33 122.63(16) . . ? C28 C29 C30 122.31(16) . . ? C29 C28 C27 117.50(17) . . ? C29 C28 C32 121.47(16) . . ? C27 C28 C32 121.02(18) . . ? C26 C27 C28 122.03(17) . . ? C27 C26 C7 120.38(15) . . ? C27 C26 C31 117.38(16) . . ? C7 C26 C31 122.19(16) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 31.74 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.352 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.064 #-- #-- _database_code_depnum_ccdc_archive 'CCDC 963974'