# Supplementary Material (ESI) for Photochemical & Photobiological Sciences # This journal is © The Royal Society of Chemistry and Owner Societies 2002 data_global _journal_coden_Cambridge 568 _publ_requested_journal 'Photochemical & Photobiological Sciences' loop_ _publ_author_name 'Vishnumurthy, Kodumuru' 'Row, Tayur N Guru' 'Venkatesan, Kailasam' _publ_contact_author_name 'Dr Kodumuru Vishnumurthy' _publ_contact_author_address ; Chemistry, BCRI Complex Northern Lipids Inc 3650 Wesbrrok Mall Vancouver, BC, Canada V6S 2L2 CANADA ; _publ_contact_author_email 'KVISHNUMURTHY@HOTMAIL.COM' _publ_section_title ; Photochemical behaviour of 4-styrylcoumarin polymorphs in the crystalline state ; data_cry2 _database_code_CSD 186875 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 4-(3-Fluorostyryl)coumarin _chemical_formula_moiety C17H11FO2 _chemical_formula_sum 'C17 H11 F O2' _chemical_formula_weight 266.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 'F' 'F' 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Pc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' _cell_length_a 6.879(3) _cell_length_b 3.9290(10) _cell_length_c 23.459(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.35(4) _cell_angle_gamma 90.00 _cell_volume 634.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needles _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 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 276 _exptl_absorpt_coefficient_mu 0.833 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius-CAD4' _diffrn_measurement_method 'omega/2 theta' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.13 _diffrn_reflns_number 1036 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 1.1553 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.77 _diffrn_reflns_theta_max 59.79 _reflns_number_total 1036 _reflns_number_gt 139 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0022P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(4) _refine_ls_number_reflns 1036 _refine_ls_number_parameters 181 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0482 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0586 _refine_ls_wR_factor_gt 0.0556 _refine_ls_goodness_of_fit_ref 0.451 _refine_ls_restrained_S_all 0.451 _refine_ls_shift/su_max 0.039 _refine_ls_shift/su_mean 0.981 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C5 C 0.603(5) 0.641(10) 0.2235(15) 0.073(12) Uani 1 d . . . H5 H 0.4978 0.5839 0.2003 0.088 Uiso 1 calc R . . C4 C 0.777(4) 0.893(9) 0.1383(12) 0.055(10) Uani 1 d . . . C10 C 0.924(4) 0.861(9) 0.2370(16) 0.059(10) Uani 1 d . . . C9 C 0.767(5) 0.801(8) 0.1986(12) 0.053(10) Uani 1 d . . . C3 C 0.941(4) 1.061(9) 0.1236(18) 0.062(10) Uani 1 d . . . H3 H 0.9522 1.1420 0.0866 0.075 Uiso 1 calc R . . C6 C 0.595(8) 0.569(11) 0.2793(17) 0.11(2) Uani 1 d . . . H6 H 0.4809 0.4815 0.2942 0.129 Uiso 1 calc R . . C7 C 0.750(5) 0.620(11) 0.3147(16) 0.072(11) Uani 1 d . . . H7 H 0.7434 0.5474 0.3524 0.086 Uiso 1 calc R . . O1 O 1.086(3) 1.014(8) 0.2201(8) 0.083(9) Uani 1 d . . . O2 O 1.254(4) 1.297(8) 0.1501(10) 0.095(8) Uani 1 d . . . C8 C 0.910(8) 0.771(12) 0.2966(13) 0.11(2) Uani 1 d . . . H8 H 1.0114 0.8187 0.3218 0.133 Uiso 1 calc R . . C2 C 1.108(4) 1.123(9) 0.1661(15) 0.058(10) Uani 1 d . . . C12 C 0.624(6) 0.910(10) 0.0455(16) 0.087(13) Uani 1 d . . . H12 H 0.7307 1.0403 0.0344 0.104 Uiso 1 calc R . . C11 C 0.619(4) 0.813(8) 0.0974(12) 0.056(8) Uani 1 d . . . H11 H 0.5121 0.6892 0.1098 0.067 Uiso 1 calc R . . F15 F 0.001(3) 0.487(6) -0.0103(12) 0.104(8) Uani 1 d . . . C14 C 0.297(5) 0.685(12) 0.0153(18) 0.09(2) Uani 1 d . . . H14 H 0.2674 0.6399 0.0532 0.104 Uiso 1 calc R . . C17 C 0.369(6) 0.912(10) -0.0923(15) 0.075(13) Uani 1 d . . . H17 H 0.3863 1.0039 -0.1284 0.090 Uiso 1 calc R . . C18 C 0.506(6) 0.938(9) -0.0549(14) 0.081(14) Uani 1 d . . . H18 H 0.6255 1.0263 -0.0659 0.098 Uiso 1 calc R . . C15 C 0.188(6) 0.619(10) -0.0184(16) 0.101(16) Uani 1 d . . . C13 C 0.479(5) 0.835(9) 0.0026(13) 0.054(10) Uani 1 d . . . C16 C 0.183(4) 0.736(10) -0.0789(15) 0.070(12) Uani 1 d . . . H16 H 0.0804 0.7048 -0.1042 0.084 Uiso 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 C5 0.065(18) 0.03(2) 0.12(3) -0.04(2) 0.01(2) -0.016(16) C4 0.048(17) 0.07(3) 0.046(17) 0.015(16) 0.015(14) 0.04(2) C10 0.040(17) 0.04(2) 0.10(3) -0.018(19) -0.015(18) 0.005(16) C9 0.07(3) 0.026(18) 0.06(2) -0.020(17) 0.01(2) -0.004(18) C3 0.022(15) 0.07(3) 0.10(3) -0.01(2) -0.007(16) 0.023(18) C6 0.13(6) 0.09(4) 0.11(4) 0.04(3) 0.04(4) 0.03(4) C7 0.07(2) 0.09(3) 0.05(2) 0.020(19) 0.04(2) 0.04(2) O1 0.10(2) 0.11(3) 0.046(12) 0.003(13) -0.017(14) -0.004(18) O2 0.104(18) 0.10(2) 0.085(16) -0.008(15) 0.000(17) -0.053(18) C8 0.17(6) 0.11(5) 0.04(2) 0.04(2) 0.03(3) 0.10(5) C2 0.022(10) 0.05(3) 0.10(3) 0.00(2) -0.017(14) -0.007(16) C12 0.12(3) 0.08(3) 0.06(2) 0.00(2) 0.03(3) -0.05(3) C11 0.08(2) 0.055(19) 0.033(15) 0.011(15) -0.010(16) -0.01(2) F15 0.082(16) 0.10(2) 0.13(2) -0.014(17) 0.016(14) -0.029(17) C14 0.04(2) 0.08(4) 0.14(5) -0.04(4) 0.05(3) -0.04(2) C17 0.11(3) 0.06(3) 0.056(18) -0.002(19) 0.03(2) 0.01(3) C18 0.12(4) 0.07(3) 0.06(2) -0.025(19) -0.01(2) -0.01(3) C15 0.18(5) 0.07(3) 0.05(2) 0.025(19) 0.04(2) -0.06(3) C13 0.05(2) 0.05(2) 0.06(2) -0.010(17) -0.01(2) 0.01(2) C16 0.028(15) 0.08(3) 0.10(3) -0.04(3) -0.003(16) -0.025(17) _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 C5 C6 1.34(5) . ? C5 C9 1.42(4) . ? C5 H5 0.9300 . ? C4 C3 1.35(4) . ? C4 C9 1.46(4) . ? C4 C11 1.48(4) . ? C10 O1 1.33(4) . ? C10 C9 1.42(4) . ? C10 C8 1.45(5) . ? C3 C2 1.54(4) . ? C3 H3 0.9300 . ? C6 C7 1.36(6) . ? C6 H6 0.9300 . ? C7 C8 1.32(7) . ? C7 H7 0.9300 . ? O1 C2 1.34(4) . ? O2 C2 1.28(4) . ? C8 H8 0.9300 . ? C12 C11 1.27(3) . ? C12 C13 1.44(5) . ? C12 H12 0.9300 . ? C11 H11 0.9300 . ? F15 C15 1.40(4) . ? C14 C15 1.12(6) . ? C14 C13 1.42(4) . ? C14 H14 0.9300 . ? C17 C18 1.29(5) . ? C17 C16 1.49(5) . ? C17 H17 0.9300 . ? C18 C13 1.42(5) . ? C18 H18 0.9300 . ? C15 C16 1.49(5) . ? C16 H16 0.9300 . ? 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 C5 C9 122(4) . . ? C6 C5 H5 120.2 . . ? C9 C5 H5 117.7 . . ? C3 C4 C9 114(4) . . ? C3 C4 C11 123(3) . . ? C9 C4 C11 123(3) . . ? O1 C10 C9 121(3) . . ? O1 C10 C8 117(4) . . ? C9 C10 C8 121(4) . . ? C10 C9 C5 115(3) . . ? C10 C9 C4 122(3) . . ? C5 C9 C4 123(3) . . ? C4 C3 C2 122(4) . . ? C4 C3 H3 118.1 . . ? C2 C3 H3 119.6 . . ? C5 C6 C7 122(5) . . ? C5 C6 H6 118.3 . . ? C7 C6 H6 119.7 . . ? C6 C7 C8 121(4) . . ? C6 C7 H7 118.4 . . ? C8 C7 H7 120.2 . . ? C2 O1 C10 122(3) . . ? C7 C8 C10 119(5) . . ? C7 C8 H8 121.7 . . ? C10 C8 H8 119.5 . . ? O2 C2 O1 123(3) . . ? O2 C2 C3 119(3) . . ? O1 C2 C3 118(3) . . ? C11 C12 C13 125(3) . . ? C11 C12 H12 117.2 . . ? C13 C12 H12 117.4 . . ? C12 C11 C4 122(3) . . ? C12 C11 H11 119.2 . . ? C4 C11 H11 118.8 . . ? C15 C14 C13 123(5) . . ? C15 C14 H14 118.3 . . ? C13 C14 H14 119.0 . . ? C18 C17 C16 121(4) . . ? C18 C17 H17 119.6 . . ? C16 C17 H17 119.0 . . ? C17 C18 C13 122(4) . . ? C17 C18 H18 118.5 . . ? C13 C18 H18 119.9 . . ? C14 C15 F15 127(4) . . ? C14 C15 C16 128(4) . . ? F15 C15 C16 103(4) . . ? C14 C13 C12 123(4) . . ? C14 C13 C18 116(4) . . ? C12 C13 C18 121(4) . . ? C17 C16 C15 109(3) . . ? C17 C16 H16 125.8 . . ? C15 C16 H16 124.7 . . ? 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 O1 C10 C9 C5 -179(3) . . . . ? C8 C10 C9 C5 -2(4) . . . . ? O1 C10 C9 C4 3(4) . . . . ? C8 C10 C9 C4 179(4) . . . . ? C6 C5 C9 C10 3(5) . . . . ? C6 C5 C9 C4 -178(4) . . . . ? C3 C4 C9 C10 -5(5) . . . . ? C11 C4 C9 C10 176(3) . . . . ? C3 C4 C9 C5 176(3) . . . . ? C11 C4 C9 C5 -2(5) . . . . ? C9 C4 C3 C2 5(5) . . . . ? C11 C4 C3 C2 -176(3) . . . . ? C9 C5 C6 C7 -5(7) . . . . ? C5 C6 C7 C8 6(7) . . . . ? C9 C10 O1 C2 0(5) . . . . ? C8 C10 O1 C2 -177(3) . . . . ? C6 C7 C8 C10 -4(6) . . . . ? O1 C10 C8 C7 179(4) . . . . ? C9 C10 C8 C7 3(5) . . . . ? C10 O1 C2 O2 174(4) . . . . ? C10 O1 C2 C3 -1(5) . . . . ? C4 C3 C2 O2 -177(4) . . . . ? C4 C3 C2 O1 -2(5) . . . . ? C13 C12 C11 C4 178(4) . . . . ? C3 C4 C11 C12 -2(6) . . . . ? C9 C4 C11 C12 176(3) . . . . ? C16 C17 C18 C13 -7(6) . . . . ? C13 C14 C15 F15 -177(4) . . . . ? C13 C14 C15 C16 -15(9) . . . . ? C15 C14 C13 C12 -178(5) . . . . ? C15 C14 C13 C18 8(7) . . . . ? C11 C12 C13 C14 10(6) . . . . ? C11 C12 C13 C18 -176(4) . . . . ? C17 C18 C13 C14 3(6) . . . . ? C17 C18 C13 C12 -171(4) . . . . ? C18 C17 C16 C15 2(6) . . . . ? C14 C15 C16 C17 10(7) . . . . ? F15 C15 C16 C17 175(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 59.79 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.095 _refine_diff_density_min -0.095 _refine_diff_density_rms 0.027 data_cry1 _database_code_CSD 186876 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 4-Styrylcoumarin _chemical_formula_moiety C17H12O2 _chemical_formula_sum 'C17 H12 O2' _chemical_formula_weight 248.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0492 0.0322 '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/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 17.057(3) _cell_length_b 8.229(3) _cell_length_c 18.261(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.33(2) _cell_angle_gamma 90.00 _cell_volume 2547.5(11) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.673 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius Cad4' _diffrn_measurement_method 'omega/2 theta' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.15 _diffrn_reflns_number 3964 _diffrn_reflns_av_R_equivalents 0.0172 _diffrn_reflns_av_sigmaI/netI 0.0163 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.37 _diffrn_reflns_theta_max 60.68 _reflns_number_total 3818 _reflns_number_gt 2841 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0619P)^2^+0.6542P] 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 3818 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0675 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1338 _refine_ls_wR_factor_gt 0.1146 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _refine_ls_shift/su_max 0.130 _refine_ls_shift/su_mean 0.005 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1B O -0.00315(9) 0.22597(19) 0.92422(7) 0.0628(4) Uani 1 d . . . O2B O -0.10499(10) 0.0860(2) 0.87622(8) 0.0777(5) Uani 1 d . . . C2B C -0.06968(13) 0.1384(3) 0.93222(12) 0.0599(6) Uani 1 d . . . C3B C -0.09143(14) 0.1190(3) 1.00521(12) 0.0600(6) Uani 1 d . . . H3B H -0.1378(14) 0.061(3) 1.0070(12) 0.072 Uiso 1 d . . . C4B C -0.05085(12) 0.1856(3) 1.06512(11) 0.0553(5) Uani 1 d . . . C5B C 0.06823(14) 0.3532(3) 1.11147(13) 0.0640(6) Uani 1 d . . . H5B H 0.0563(13) 0.344(3) 1.1629(13) 0.077 Uiso 1 d . . . C7B C 0.15145(15) 0.4553(3) 1.02549(15) 0.0740(7) Uani 1 d . . . H7B H 0.2003(16) 0.517(3) 1.0167(13) 0.089 Uiso 1 d . . . C8B C 0.10568(15) 0.3812(3) 0.96867(14) 0.0696(7) Uani 1 d . . . H8B H 0.1154(14) 0.393(3) 0.9176(14) 0.083 Uiso 1 d . . . C9B C 0.01942(12) 0.2780(3) 1.05479(11) 0.0539(5) Uani 1 d . . . C10B C 0.04048(12) 0.2948(3) 0.98398(11) 0.0555(5) Uani 1 d . . . C12B C -0.12895(15) 0.0748(3) 1.16002(13) 0.0697(7) Uani 1 d . . . H12B H -0.1550(15) 0.006(3) 1.1249(14) 0.084 Uiso 1 d . . . C13B C -0.15382(14) 0.0642(3) 1.23378(13) 0.0704(7) Uani 1 d . . . C15B C -0.1469(2) 0.1506(5) 1.35996(16) 0.0992(10) Uani 1 d . . . H15B H -0.1215(18) 0.221(4) 1.4001(18) 0.119 Uiso 1 d . . . C11B C -0.07508(15) 0.1691(3) 1.13898(13) 0.0684(6) Uani 1 d . . . H11B H -0.0487(14) 0.241(3) 1.1744(13) 0.082 Uiso 1 d . . . C6B C 0.13280(15) 0.4403(3) 1.09668(14) 0.0725(7) Uani 1 d . . . H6B H 0.1673(15) 0.497(3) 1.1378(14) 0.087 Uiso 1 d . . . C14B C -0.12167(17) 0.1611(4) 1.29128(14) 0.0851(8) Uani 1 d . . . H14B H -0.0773(17) 0.235(4) 1.2838(15) 0.102 Uiso 1 d . . . C18B C -0.21228(19) -0.0430(4) 1.24763(18) 0.0980(10) Uani 1 d . . . H18B H -0.2341(19) -0.107(4) 1.2083(17) 0.118 Uiso 1 d . . . C16B C -0.2043(2) 0.0419(6) 1.3726(2) 0.1089(12) Uani 1 d . . . H16B H -0.2187(19) 0.043(4) 1.4242(19) 0.131 Uiso 1 d . . . C17B C -0.2369(2) -0.0513(6) 1.3171(2) 0.1225(14) Uani 1 d . . . H17B H -0.274(2) -0.127(5) 1.324(2) 0.147 Uiso 1 d . . . C3A C 0.28048(16) 0.1462(3) 1.10279(12) 0.0670(6) Uani 1 d . . . H3A H 0.2257(15) 0.153(3) 1.0993(13) 0.080 Uiso 1 d . . . O1A O 0.39370(10) 0.1045(2) 1.03907(8) 0.0779(5) Uani 1 d . . . C4A C 0.32410(13) 0.1621(3) 1.16874(11) 0.0589(6) Uani 1 d . . . C10A C 0.44083(15) 0.1192(3) 1.10525(12) 0.0678(6) Uani 1 d . . . C14A C 0.20628(16) 0.2262(3) 1.37666(13) 0.0684(6) Uani 1 d . . . H14A H 0.2550(15) 0.281(3) 1.3791(13) 0.082 Uiso 1 d . . . C13A C 0.17534(13) 0.1475(3) 1.31216(12) 0.0597(6) Uani 1 d . . . C15A C 0.16777(19) 0.2188(4) 1.43891(15) 0.0828(8) Uani 1 d . . . H15A H 0.1924(16) 0.266(4) 1.4853(15) 0.099 Uiso 1 d . . . C12A C 0.21586(15) 0.1388(3) 1.24577(12) 0.0614(6) Uani 1 d . . . H12A H 0.1865(13) 0.082(3) 1.2055(13) 0.074 Uiso 1 d . . . C18A C 0.10452(15) 0.0668(3) 1.31283(15) 0.0742(7) Uani 1 d . . . H18A H 0.0840(15) 0.015(3) 1.2707(14) 0.089 Uiso 1 d . . . C11A C 0.28762(14) 0.1887(3) 1.23650(12) 0.0615(6) Uani 1 d . . . H11A H 0.3200(13) 0.251(3) 1.2767(13) 0.074 Uiso 1 d . . . C17A C 0.06630(18) 0.0599(4) 1.37520(18) 0.0882(8) Uani 1 d . . . H17A H 0.0168(18) -0.005(4) 1.3731(15) 0.106 Uiso 1 d . . . C16A C 0.0983(2) 0.1347(4) 1.43860(18) 0.0911(9) Uani 1 d . . . H16A H 0.0724(17) 0.120(4) 1.4834(16) 0.109 Uiso 1 d . . . C9A C 0.40908(14) 0.1480(3) 1.17067(12) 0.0610(6) Uani 1 d . . . C5A C 0.46240(16) 0.1607(4) 1.23422(14) 0.0768(7) Uani 1 d . . . H5A H 0.4403(15) 0.184(3) 1.2796(15) 0.092 Uiso 1 d . . . O2A O 0.27662(12) 0.0885(3) 0.97617(9) 0.0953(6) Uani 1 d . . . C2A C 0.31290(16) 0.1117(3) 1.03589(13) 0.0730(7) Uani 1 d . . . C8A C 0.52058(17) 0.1030(4) 1.10200(17) 0.0879(9) Uani 1 d . . . H8A H 0.5397(17) 0.086(4) 1.0559(16) 0.106 Uiso 1 d . . . C7A C 0.57104(19) 0.1173(5) 1.16526(19) 0.0996(10) Uani 1 d . . . H7A H 0.6241(19) 0.111(4) 1.1651(16) 0.120 Uiso 1 d . . . C6A C 0.54165(18) 0.1456(5) 1.23159(17) 0.0972(10) Uani 1 d . . . H6A H 0.5782(18) 0.158(4) 1.2739(17) 0.117 Uiso 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 O1B 0.0749(10) 0.0679(10) 0.0459(8) 0.0033(7) 0.0079(7) 0.0000(8) O2B 0.0893(11) 0.0902(12) 0.0504(9) -0.0041(8) -0.0062(8) -0.0074(10) C2B 0.0675(14) 0.0604(14) 0.0508(13) 0.0050(10) 0.0021(11) 0.0059(12) C3B 0.0632(13) 0.0623(15) 0.0544(13) -0.0005(11) 0.0058(11) 0.0013(11) C4B 0.0588(12) 0.0575(13) 0.0506(12) 0.0009(10) 0.0106(10) 0.0082(10) C5B 0.0700(14) 0.0704(15) 0.0520(13) -0.0067(11) 0.0082(11) 0.0026(12) C7B 0.0671(15) 0.0772(17) 0.0798(17) -0.0050(14) 0.0185(13) -0.0052(13) C8B 0.0754(16) 0.0754(17) 0.0606(14) 0.0035(12) 0.0194(12) -0.0023(13) C9B 0.0571(12) 0.0542(12) 0.0511(12) -0.0005(10) 0.0092(9) 0.0080(10) C10B 0.0620(13) 0.0554(13) 0.0493(12) 0.0004(10) 0.0063(10) 0.0092(11) C12B 0.0730(15) 0.0780(17) 0.0596(14) -0.0048(12) 0.0140(12) -0.0041(14) C13B 0.0662(14) 0.0818(18) 0.0661(15) 0.0044(13) 0.0202(12) 0.0031(13) C15B 0.095(2) 0.140(3) 0.0663(17) -0.0076(18) 0.0248(15) 0.003(2) C11B 0.0688(15) 0.0847(18) 0.0529(13) -0.0076(12) 0.0121(11) -0.0068(14) C6B 0.0669(15) 0.0808(18) 0.0700(15) -0.0132(13) 0.0084(12) -0.0054(13) C14B 0.0816(18) 0.116(2) 0.0611(15) -0.0072(15) 0.0231(13) -0.0107(17) C18B 0.099(2) 0.108(3) 0.094(2) -0.0063(18) 0.0388(18) -0.0235(19) C16B 0.105(2) 0.149(3) 0.081(2) 0.015(2) 0.047(2) 0.007(2) C17B 0.117(3) 0.143(4) 0.118(3) 0.008(3) 0.059(2) -0.030(2) C3A 0.0792(15) 0.0721(16) 0.0502(13) 0.0037(11) 0.0088(12) 0.0047(14) O1A 0.0918(12) 0.0934(13) 0.0511(9) -0.0060(8) 0.0200(8) -0.0062(10) C4A 0.0752(15) 0.0532(13) 0.0493(12) 0.0019(10) 0.0116(11) -0.0010(11) C10A 0.0795(16) 0.0693(16) 0.0565(14) -0.0045(11) 0.0164(12) -0.0018(13) C14A 0.0750(15) 0.0703(16) 0.0617(14) -0.0059(12) 0.0149(12) 0.0037(13) C13A 0.0641(13) 0.0586(14) 0.0571(13) 0.0013(11) 0.0101(10) 0.0083(11) C15A 0.103(2) 0.083(2) 0.0640(16) -0.0063(14) 0.0211(15) 0.0110(17) C12A 0.0725(15) 0.0601(14) 0.0518(12) -0.0025(10) 0.0068(11) 0.0031(12) C18A 0.0723(16) 0.0758(18) 0.0759(17) -0.0013(14) 0.0139(13) 0.0005(14) C11A 0.0719(15) 0.0613(15) 0.0516(13) -0.0031(11) 0.0093(11) -0.0001(12) C17A 0.0797(18) 0.088(2) 0.103(2) 0.0012(17) 0.0340(17) 0.0010(16) C16A 0.107(2) 0.089(2) 0.086(2) 0.0038(17) 0.0478(18) 0.0121(18) C9A 0.0741(14) 0.0587(14) 0.0514(12) -0.0005(10) 0.0128(11) -0.0023(11) C5A 0.0771(17) 0.093(2) 0.0614(15) -0.0059(14) 0.0123(13) -0.0030(14) O2A 0.1118(14) 0.1262(17) 0.0468(9) -0.0010(10) 0.0037(9) -0.0088(12) C2A 0.0882(18) 0.0804(18) 0.0515(14) 0.0017(12) 0.0121(13) -0.0051(14) C8A 0.0874(19) 0.103(2) 0.0774(18) -0.0132(16) 0.0290(16) -0.0026(17) C7A 0.0727(17) 0.131(3) 0.098(2) -0.011(2) 0.0204(17) -0.0012(19) C6A 0.0755(19) 0.137(3) 0.0786(19) -0.0062(19) 0.0057(14) -0.0013(19) _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 O1B C2B 1.366(3) . ? O1B C10B 1.374(2) . ? O2B C2B 1.207(2) . ? C2B C3B 1.431(3) . ? C3B C4B 1.345(3) . ? C3B H3B 0.92(2) . ? C4B C9B 1.449(3) . ? C4B C11B 1.460(3) . ? C5B C6B 1.365(3) . ? C5B C9B 1.399(3) . ? C5B H5B 0.99(2) . ? C7B C8B 1.371(3) . ? C7B C6B 1.378(3) . ? C7B H7B 1.00(3) . ? C8B C10B 1.374(3) . ? C8B H8B 0.97(2) . ? C9B C10B 1.387(3) . ? C12B C11B 1.294(3) . ? C12B C13B 1.459(3) . ? C12B H12B 0.93(3) . ? C13B C18B 1.376(4) . ? C13B C14B 1.383(4) . ? C15B C16B 1.364(5) . ? C15B C14B 1.373(4) . ? C15B H15B 0.99(3) . ? C11B H11B 0.95(3) . ? C6B H6B 1.01(3) . ? C14B H14B 0.99(3) . ? C18B C17B 1.381(4) . ? C18B H18B 0.93(3) . ? C16B C17B 1.342(5) . ? C16B H16B 1.00(3) . ? C17B H17B 0.91(4) . ? C3A C4A 1.350(3) . ? C3A C2A 1.424(3) . ? C3A H3A 0.93(2) . ? O1A C2A 1.374(3) . ? O1A C10A 1.381(3) . ? C4A C9A 1.451(3) . ? C4A C11A 1.461(3) . ? C10A C8A 1.375(4) . ? C10A C9A 1.385(3) . ? C14A C15A 1.375(3) . ? C14A C13A 1.396(3) . ? C14A H14A 0.94(3) . ? C13A C18A 1.380(3) . ? C13A C12A 1.462(3) . ? C15A C16A 1.371(4) . ? C15A H15A 0.98(3) . ? C12A C11A 1.320(3) . ? C12A H12A 0.96(2) . ? C18A C17A 1.374(4) . ? C18A H18A 0.91(3) . ? C11A H11A 1.01(2) . ? C17A C16A 1.371(4) . ? C17A H17A 0.99(3) . ? C16A H16A 0.98(3) . ? C9A C5A 1.397(3) . ? C5A C6A 1.364(4) . ? C5A H5A 0.97(3) . ? O2A C2A 1.208(3) . ? C8A C7A 1.367(4) . ? C8A H8A 0.95(3) . ? C7A C6A 1.381(4) . ? C7A H7A 0.91(3) . ? C6A H6A 0.94(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 C2B O1B C10B 121.09(17) . . ? O2B C2B O1B 116.1(2) . . ? O2B C2B C3B 126.3(2) . . ? O1B C2B C3B 117.5(2) . . ? C4B C3B C2B 123.3(2) . . ? C4B C3B H3B 123.1(14) . . ? C2B C3B H3B 113.6(14) . . ? C3B C4B C9B 117.83(19) . . ? C3B C4B C11B 122.7(2) . . ? C9B C4B C11B 119.4(2) . . ? C6B C5B C9B 120.9(2) . . ? C6B C5B H5B 118.9(14) . . ? C9B C5B H5B 120.2(14) . . ? C8B C7B C6B 120.2(3) . . ? C8B C7B H7B 121.2(14) . . ? C6B C7B H7B 118.6(15) . . ? C7B C8B C10B 118.8(2) . . ? C7B C8B H8B 122.6(15) . . ? C10B C8B H8B 118.4(15) . . ? C10B C9B C5B 116.8(2) . . ? C10B C9B C4B 118.48(19) . . ? C5B C9B C4B 124.69(19) . . ? O1B C10B C8B 115.56(19) . . ? O1B C10B C9B 121.8(2) . . ? C8B C10B C9B 122.7(2) . . ? C11B C12B C13B 126.8(3) . . ? C11B C12B H12B 117.4(16) . . ? C13B C12B H12B 115.9(16) . . ? C18B C13B C14B 117.7(2) . . ? C18B C13B C12B 119.9(3) . . ? C14B C13B C12B 122.4(2) . . ? C16B C15B C14B 119.9(3) . . ? C16B C15B H15B 121.3(18) . . ? C14B C15B H15B 118.8(18) . . ? C12B C11B C4B 127.8(2) . . ? C12B C11B H11B 117.9(15) . . ? C4B C11B H11B 114.2(15) . . ? C5B C6B C7B 120.6(3) . . ? C5B C6B H6B 120.6(14) . . ? C7B C6B H6B 118.8(14) . . ? C15B C14B C13B 121.3(3) . . ? C15B C14B H14B 119.0(16) . . ? C13B C14B H14B 119.6(16) . . ? C13B C18B C17B 120.0(3) . . ? C13B C18B H18B 117(2) . . ? C17B C18B H18B 123(2) . . ? C17B C16B C15B 119.5(3) . . ? C17B C16B H16B 126(2) . . ? C15B C16B H16B 114(2) . . ? C16B C17B C18B 121.5(3) . . ? C16B C17B H17B 122(2) . . ? C18B C17B H17B 117(3) . . ? C4A C3A C2A 123.8(2) . . ? C4A C3A H3A 120.3(15) . . ? C2A C3A H3A 115.8(15) . . ? C2A O1A C10A 121.16(18) . . ? C3A C4A C9A 117.7(2) . . ? C3A C4A C11A 121.7(2) . . ? C9A C4A C11A 120.6(2) . . ? C8A C10A O1A 115.9(2) . . ? C8A C10A C9A 122.5(2) . . ? O1A C10A C9A 121.6(2) . . ? C15A C14A C13A 120.4(3) . . ? C15A C14A H14A 118.8(15) . . ? C13A C14A H14A 120.8(15) . . ? C18A C13A C14A 117.8(2) . . ? C18A C13A C12A 118.6(2) . . ? C14A C13A C12A 123.6(2) . . ? C16A C15A C14A 120.7(3) . . ? C16A C15A H15A 119.3(16) . . ? C14A C15A H15A 119.9(16) . . ? C11A C12A C13A 128.4(2) . . ? C11A C12A H12A 117.7(13) . . ? C13A C12A H12A 113.8(14) . . ? C17A C18A C13A 121.5(3) . . ? C17A C18A H18A 120.4(17) . . ? C13A C18A H18A 118.1(17) . . ? C12A C11A C4A 123.3(2) . . ? C12A C11A H11A 120.4(13) . . ? C4A C11A H11A 116.3(13) . . ? C16A C17A C18A 120.0(3) . . ? C16A C17A H17A 122.0(17) . . ? C18A C17A H17A 118.0(17) . . ? C15A C16A C17A 119.6(3) . . ? C15A C16A H16A 121.9(18) . . ? C17A C16A H16A 118.4(18) . . ? C10A C9A C5A 116.7(2) . . ? C10A C9A C4A 118.5(2) . . ? C5A C9A C4A 124.8(2) . . ? C6A C5A C9A 121.4(3) . . ? C6A C5A H5A 122.0(16) . . ? C9A C5A H5A 116.6(16) . . ? O2A C2A O1A 116.3(2) . . ? O2A C2A C3A 126.7(3) . . ? O1A C2A C3A 117.0(2) . . ? C7A C8A C10A 119.3(3) . . ? C7A C8A H8A 121.2(18) . . ? C10A C8A H8A 119.5(18) . . ? C8A C7A C6A 120.0(3) . . ? C8A C7A H7A 122(2) . . ? C6A C7A H7A 118(2) . . ? C5A C6A C7A 120.2(3) . . ? C5A C6A H6A 122.0(19) . . ? C7A C6A H6A 117.7(19) . . ? 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 C10B O1B C2B O2B 178.28(19) . . . . ? C10B O1B C2B C3B -1.0(3) . . . . ? O2B C2B C3B C4B -177.5(2) . . . . ? O1B C2B C3B C4B 1.7(3) . . . . ? C2B C3B C4B C9B -1.6(3) . . . . ? C2B C3B C4B C11B 178.0(2) . . . . ? C6B C7B C8B C10B 1.2(4) . . . . ? C6B C5B C9B C10B 0.7(3) . . . . ? C6B C5B C9B C4B -179.0(2) . . . . ? C3B C4B C9B C10B 0.9(3) . . . . ? C11B C4B C9B C10B -178.7(2) . . . . ? C3B C4B C9B C5B -179.4(2) . . . . ? C11B C4B C9B C5B 1.0(3) . . . . ? C2B O1B C10B C8B -179.4(2) . . . . ? C2B O1B C10B C9B 0.4(3) . . . . ? C7B C8B C10B O1B 179.1(2) . . . . ? C7B C8B C10B C9B -0.7(4) . . . . ? C5B C9B C10B O1B 179.97(19) . . . . ? C4B C9B C10B O1B -0.3(3) . . . . ? C5B C9B C10B C8B -0.3(3) . . . . ? C4B C9B C10B C8B 179.5(2) . . . . ? C11B C12B C13B C18B -179.9(3) . . . . ? C11B C12B C13B C14B 1.3(4) . . . . ? C13B C12B C11B C4B -177.9(2) . . . . ? C3B C4B C11B C12B 10.6(4) . . . . ? C9B C4B C11B C12B -169.8(3) . . . . ? C9B C5B C6B C7B -0.2(4) . . . . ? C8B C7B C6B C5B -0.8(4) . . . . ? C16B C15B C14B C13B 0.6(5) . . . . ? C18B C13B C14B C15B 0.2(5) . . . . ? C12B C13B C14B C15B 179.0(3) . . . . ? C14B C13B C18B C17B -0.1(5) . . . . ? C12B C13B C18B C17B -178.9(3) . . . . ? C14B C15B C16B C17B -1.6(6) . . . . ? C15B C16B C17B C18B 1.7(7) . . . . ? C13B C18B C17B C16B -0.9(6) . . . . ? C2A C3A C4A C9A 2.0(4) . . . . ? C2A C3A C4A C11A -176.5(2) . . . . ? C2A O1A C10A C8A 177.2(2) . . . . ? C2A O1A C10A C9A -2.6(4) . . . . ? C15A C14A C13A C18A 1.6(4) . . . . ? C15A C14A C13A C12A -174.9(2) . . . . ? C13A C14A C15A C16A -0.2(4) . . . . ? C18A C13A C12A C11A -170.7(2) . . . . ? C14A C13A C12A C11A 5.7(4) . . . . ? C14A C13A C18A C17A -1.6(4) . . . . ? C12A C13A C18A C17A 175.1(2) . . . . ? C13A C12A C11A C4A 175.2(2) . . . . ? C3A C4A C11A C12A 27.2(4) . . . . ? C9A C4A C11A C12A -151.3(2) . . . . ? C13A C18A C17A C16A 0.2(5) . . . . ? C14A C15A C16A C17A -1.2(5) . . . . ? C18A C17A C16A C15A 1.2(5) . . . . ? C8A C10A C9A C5A 0.3(4) . . . . ? O1A C10A C9A C5A -180.0(2) . . . . ? C8A C10A C9A C4A -179.6(3) . . . . ? O1A C10A C9A C4A 0.2(3) . . . . ? C3A C4A C9A C10A 0.1(3) . . . . ? C11A C4A C9A C10A 178.6(2) . . . . ? C3A C4A C9A C5A -179.7(3) . . . . ? C11A C4A C9A C5A -1.2(4) . . . . ? C10A C9A C5A C6A 0.1(4) . . . . ? C4A C9A C5A C6A 179.9(3) . . . . ? C10A O1A C2A O2A -176.0(2) . . . . ? C10A O1A C2A C3A 4.3(3) . . . . ? C4A C3A C2A O2A 176.2(3) . . . . ? C4A C3A C2A O1A -4.2(4) . . . . ? O1A C10A C8A C7A 179.5(3) . . . . ? C9A C10A C8A C7A -0.7(5) . . . . ? C10A C8A C7A C6A 0.9(5) . . . . ? C9A C5A C6A C7A 0.1(5) . . . . ? C8A C7A C6A C5A -0.6(6) . . . . ? _diffrn_measured_fraction_theta_max 0.912 _diffrn_reflns_theta_full 60.68 _diffrn_measured_fraction_theta_full 0.912 _refine_diff_density_max 0.122 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.036