# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_nase_7_0m _database_code_depnum_ccdc_archive 'CCDC 895985' #TrackingRef 'Nase7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H10 O2 S' _chemical_formula_sum 'C20 H10 O2 S' _chemical_formula_weight 314.34 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.7261(7) _cell_length_b 6.3804(4) _cell_length_c 19.3742(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.906(2) _cell_angle_gamma 90.00 _cell_volume 1449.34(15) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 3457 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 29.75 _exptl_crystal_description irregular _exptl_crystal_colour yellow _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.441 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.230 _exptl_absorpt_correction_type 'multi scan' _exptl_absorpt_correction_T_min 0.8976 _exptl_absorpt_correction_T_max 0.9729 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _exptl_special_details ? _diffrn_ambient_temperature 153(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 '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_% <1% _diffrn_reflns_number 11776 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3144 _reflns_number_gt 2400 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa APEX 2 (Bruker-AXS)' _computing_cell_refinement 'SAINT-NT (Sheldrick, 2008)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia)' _computing_publication_material 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^)+(0.0746P)^2^+0.3338P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3144 _refine_ls_number_parameters 221 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0621 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1398 _refine_ls_wR_factor_gt 0.1171 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.41342(11) 0.6661(2) 0.41788(8) 0.0544(4) Uani 1 1 d . . . O2 O -0.02812(11) 0.4428(2) 0.40546(8) 0.0503(4) Uani 1 1 d . . . S1 S 0.31607(11) 1.89748(14) 0.13737(6) 0.0609(4) Uani 0.683(3) 1 d P A 1 S1A S 0.4432(3) 1.8058(7) 0.1562(2) 0.0706(11) Uani 0.317(3) 1 d PD A 2 C1 C 0.18625(15) 1.0574(3) 0.31103(9) 0.0339(4) Uani 1 1 d . . . C2 C 0.26374(14) 0.9308(3) 0.34702(9) 0.0326(4) Uani 1 1 d . . . H2 H 0.3421 0.9688 0.3491 0.039 Uiso 1 1 calc R . . C3 C 0.22734(13) 0.7495(3) 0.37986(8) 0.0298(4) Uani 1 1 d . . . C4 C 0.31288(14) 0.6177(3) 0.41706(9) 0.0347(4) Uani 1 1 d . . . C5 C 0.27181(15) 0.4255(3) 0.45242(8) 0.0328(4) Uani 1 1 d . . . C6 C 0.34916(17) 0.2994(3) 0.48838(10) 0.0421(4) Uani 1 1 d . . . H6 H 0.4279 0.3349 0.4896 0.051 Uiso 1 1 calc R . . C7 C 0.3113(2) 0.1216(3) 0.52256(10) 0.0488(5) Uani 1 1 d . . . H7 H 0.3641 0.0357 0.5473 0.059 Uiso 1 1 calc R . . C8 C 0.1973(2) 0.0699(3) 0.52058(10) 0.0489(5) Uani 1 1 d . . . H8 H 0.1718 -0.0517 0.5441 0.059 Uiso 1 1 calc R . . C9 C 0.11989(17) 0.1926(3) 0.48491(10) 0.0426(5) Uani 1 1 d . . . H9 H 0.0414 0.1555 0.4839 0.051 Uiso 1 1 calc R . . C10 C 0.15657(15) 0.3716(3) 0.45024(9) 0.0334(4) Uani 1 1 d . . . C11 C 0.07139(14) 0.4979(3) 0.41080(9) 0.0343(4) Uani 1 1 d . . . C12 C 0.11180(14) 0.6932(3) 0.37729(8) 0.0305(4) Uani 1 1 d . . . C13 C 0.03394(15) 0.8219(3) 0.34182(9) 0.0359(4) Uani 1 1 d . . . H13 H -0.0447 0.7862 0.3405 0.043 Uiso 1 1 calc R . . C14 C 0.07095(15) 1.0000(3) 0.30886(9) 0.0373(4) Uani 1 1 d . . . H14 H 0.0176 1.0851 0.2843 0.045 Uiso 1 1 calc R . . C15 C 0.22562(14) 1.2456(3) 0.27581(8) 0.0340(4) Uani 1 1 d . . . C16 C 0.25969(15) 1.3907(3) 0.24636(9) 0.0372(4) Uani 1 1 d . . . C17 C 0.30375(16) 1.5675(3) 0.20899(9) 0.0366(4) Uani 1 1 d . A . C18 C 0.42083(19) 1.6063(4) 0.20135(13) 0.0592(6) Uani 1 1 d . . . H18 H 0.4789 1.5174 0.2196 0.071 Uiso 1 1 calc R A 1 C19 C 0.4439(11) 1.796(2) 0.1629(6) 0.151(5) Uani 0.683(3) 1 d P A 1 H19 H 0.5170 1.8524 0.1537 0.181 Uiso 0.683(3) 1 calc PR A 1 C19A C 0.3074(8) 1.882(2) 0.1393(10) 0.151(5) Uani 0.317(3) 1 d PD A 2 H19A H 0.2811 1.9987 0.1132 0.181 Uiso 0.317(3) 1 calc PR A 2 C20 C 0.23798(18) 1.7161(3) 0.17600(10) 0.0433(5) Uani 1 1 d D . . H20 H 0.1570 1.7152 0.1754 0.052 Uiso 1 1 calc R A 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0347(7) 0.0474(8) 0.0807(11) 0.0159(7) -0.0085(7) -0.0041(6) O2 0.0367(7) 0.0399(8) 0.0742(10) -0.0006(7) -0.0001(6) -0.0083(6) S1 0.1163(10) 0.0288(4) 0.0382(5) 0.0025(3) 0.0178(5) -0.0055(4) S1A 0.0613(17) 0.089(2) 0.062(2) 0.0011(16) 0.0104(15) -0.0344(16) C1 0.0451(10) 0.0279(9) 0.0287(9) -0.0027(6) 0.0046(7) 0.0015(7) C2 0.0354(9) 0.0301(9) 0.0324(9) -0.0037(7) 0.0029(7) -0.0008(7) C3 0.0331(8) 0.0272(8) 0.0291(8) -0.0057(6) 0.0010(6) 0.0006(7) C4 0.0336(9) 0.0307(9) 0.0397(10) -0.0027(7) -0.0024(7) -0.0010(7) C5 0.0428(9) 0.0280(8) 0.0275(8) -0.0041(7) -0.0014(7) 0.0012(7) C6 0.0513(11) 0.0374(10) 0.0374(10) -0.0025(8) -0.0084(8) 0.0029(8) C7 0.0730(14) 0.0376(10) 0.0355(10) 0.0029(8) -0.0081(9) 0.0075(10) C8 0.0754(14) 0.0365(10) 0.0351(10) 0.0061(8) 0.0056(9) -0.0045(10) C9 0.0556(11) 0.0348(10) 0.0377(10) -0.0021(8) 0.0093(9) -0.0063(8) C10 0.0439(9) 0.0281(8) 0.0283(8) -0.0050(7) 0.0050(7) -0.0019(7) C11 0.0358(9) 0.0295(9) 0.0378(10) -0.0090(7) 0.0038(7) -0.0036(7) C12 0.0328(8) 0.0281(8) 0.0307(8) -0.0068(7) 0.0010(7) -0.0006(6) C13 0.0329(8) 0.0374(9) 0.0373(9) -0.0064(7) -0.0018(7) 0.0001(7) C14 0.0409(9) 0.0356(9) 0.0351(9) -0.0010(7) -0.0045(7) 0.0070(8) C15 0.0420(9) 0.0325(9) 0.0274(8) -0.0031(7) 0.0009(7) 0.0069(7) C16 0.0413(9) 0.0384(10) 0.0320(9) -0.0056(8) 0.0003(7) 0.0058(8) C17 0.0467(10) 0.0333(9) 0.0298(9) -0.0017(7) 0.0032(7) -0.0026(7) C18 0.0466(11) 0.0752(16) 0.0557(14) 0.0160(12) 0.0002(10) -0.0072(11) C19 0.162(10) 0.199(11) 0.090(7) -0.014(7) -0.039(6) -0.031(8) C19A 0.162(10) 0.199(11) 0.090(7) -0.014(7) -0.039(6) -0.031(8) C20 0.0559(11) 0.0383(10) 0.0360(10) 0.0002(8) 0.0060(8) 0.0051(9) _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 1.218(2) . ? O2 C11 1.222(2) . ? S1 C20 1.661(2) . ? S1 C19 1.701(14) . ? S1A C18 1.569(5) . ? S1A C19A 1.692(10) . ? C1 C2 1.394(2) . ? C1 C14 1.401(3) . ? C1 C15 1.460(2) . ? C2 C3 1.391(2) . ? C3 C12 1.402(2) . ? C3 C4 1.486(2) . ? C4 C5 1.489(2) . ? C5 C6 1.391(2) . ? C5 C10 1.394(2) . ? C6 C7 1.390(3) . ? C7 C8 1.377(3) . ? C8 C9 1.376(3) . ? C9 C10 1.396(2) . ? C10 C11 1.486(3) . ? C11 C12 1.486(2) . ? C12 C13 1.400(2) . ? C13 C14 1.377(3) . ? C15 C16 1.162(2) . ? C16 C17 1.441(2) . ? C17 C20 1.373(3) . ? C17 C18 1.405(3) . ? C18 C19 1.446(13) . ? C19A C20 1.517(9) . ? 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 C20 S1 C19 95.3(5) . . ? C18 S1A C19A 100.1(4) . . ? C2 C1 C14 119.01(16) . . ? C2 C1 C15 120.12(16) . . ? C14 C1 C15 120.87(16) . . ? C3 C2 C1 120.55(16) . . ? C2 C3 C12 120.03(15) . . ? C2 C3 C4 118.86(14) . . ? C12 C3 C4 121.10(15) . . ? O1 C4 C3 120.57(16) . . ? O1 C4 C5 121.50(16) . . ? C3 C4 C5 117.93(14) . . ? C6 C5 C10 119.77(16) . . ? C6 C5 C4 119.59(16) . . ? C10 C5 C4 120.64(15) . . ? C7 C6 C5 120.00(18) . . ? C8 C7 C6 119.95(19) . . ? C9 C8 C7 120.66(18) . . ? C8 C9 C10 120.07(19) . . ? C5 C10 C9 119.53(17) . . ? C5 C10 C11 121.68(15) . . ? C9 C10 C11 118.77(16) . . ? O2 C11 C10 121.39(16) . . ? O2 C11 C12 121.02(16) . . ? C10 C11 C12 117.59(14) . . ? C13 C12 C3 119.30(16) . . ? C13 C12 C11 119.75(15) . . ? C3 C12 C11 120.94(15) . . ? C14 C13 C12 120.25(16) . . ? C13 C14 C1 120.84(16) . . ? C16 C15 C1 177.44(18) . . ? C15 C16 C17 178.66(19) . . ? C20 C17 C18 111.82(18) . . ? C20 C17 C16 124.82(17) . . ? C18 C17 C16 123.35(18) . . ? C17 C18 C19 113.1(6) . . ? C17 C18 S1A 112.0(2) . . ? C18 C19 S1 107.3(8) . . ? C20 C19A S1A 102.7(6) . . ? C17 C20 C19A 113.4(4) . . ? C17 C20 S1 112.39(16) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.302 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.047 data_nase15new _database_code_depnum_ccdc_archive 'CCDC 895986' #TrackingRef 'Nase15new.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H13 Br O2' _chemical_formula_sum 'C16 H13 Br O2' _chemical_formula_weight 317.17 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' Br Br -0.2901 2.4595 '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 c' _symmetry_space_group_name_Hall 'C -2yc' 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' _cell_length_a 18.3586(5) _cell_length_b 8.6988(2) _cell_length_c 8.3214(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.203(2) _cell_angle_gamma 90.00 _cell_volume 1315.31(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5839 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 23.75 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.602 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 3.119 _exptl_absorpt_correction_type 'multi scan' _exptl_absorpt_correction_T_min 0.5215 _exptl_absorpt_correction_T_max 0.7885 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2004)' _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 '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_% <1% _diffrn_reflns_number 16059 _diffrn_reflns_av_R_equivalents 0.0264 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 28.04 _reflns_number_total 3172 _reflns_number_gt 2554 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Kappa APEX 2 (Bruker-AXS)' _computing_cell_refinement 'SAINT-NT (Sheldrick, 2008)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia)' _computing_publication_material 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^)+(0.0584P)^2^+0.0565P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(2) _refine_ls_number_reflns 3172 _refine_ls_number_parameters 175 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0459 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0902 _refine_ls_wR_factor_gt 0.0815 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 Br1 Br 0.12646(3) 0.61874(4) 0.02641(5) 0.07358(14) Uani 1 1 d . . . O1 O 0.27302(12) 0.4969(2) 0.0020(2) 0.0482(5) Uani 1 1 d . . . O2 O 0.43556(11) 0.9798(2) 0.3027(2) 0.0497(5) Uani 1 1 d . . . C1 C 0.31048(16) 0.6208(2) 0.0739(3) 0.0361(5) Uani 1 1 d . . . C2 C 0.27428(14) 0.7376(3) 0.1487(3) 0.0358(5) Uani 1 1 d . . . C3 C 0.19641(15) 0.7482(3) 0.1518(3) 0.0434(6) Uani 1 1 d . . . C4 C 0.16649(19) 0.8609(4) 0.2351(4) 0.0540(8) Uani 1 1 d . . . H4 H 0.1160 0.8627 0.2370 0.065 Uiso 1 1 calc R . . C5 C 0.2116(2) 0.9749(3) 0.3184(4) 0.0579(8) Uani 1 1 d . . . H5 H 0.1906 1.0501 0.3767 0.069 Uiso 1 1 calc R . . C6 C 0.28457(18) 0.9763(3) 0.3149(3) 0.0467(6) Uani 1 1 d . . . H6 H 0.3133 1.0538 0.3686 0.056 Uiso 1 1 calc R . . C7 C 0.31870(16) 0.8597(3) 0.2292(3) 0.0369(5) Uani 1 1 d . . . C8 C 0.39422(16) 0.8645(3) 0.2222(3) 0.0384(5) Uani 1 1 d . . . C9 C 0.42895(14) 0.7525(3) 0.1412(3) 0.0374(5) Uani 1 1 d . . . C10 C 0.50582(15) 0.7562(3) 0.1321(3) 0.0472(6) Uani 1 1 d . . . H10 H 0.5342 0.8372 0.1796 0.057 Uiso 1 1 calc R . . C11 C 0.53824(18) 0.6424(4) 0.0546(4) 0.0559(8) Uani 1 1 d . . . H11 H 0.5885 0.6461 0.0500 0.067 Uiso 1 1 calc R . . C12 C 0.4962(2) 0.5194(4) -0.0183(4) 0.0574(8) Uani 1 1 d . . . H12 H 0.5191 0.4431 -0.0713 0.069 Uiso 1 1 calc R . . C13 C 0.42322(17) 0.5100(3) -0.0128(3) 0.0472(6) Uani 1 1 d . . . H13 H 0.3966 0.4272 -0.0614 0.057 Uiso 1 1 calc R . . C14 C 0.38631(16) 0.6270(3) 0.0675(3) 0.0366(5) Uani 1 1 d . . . C15 C 0.2662(3) 0.3721(3) 0.1119(5) 0.0635(9) Uani 1 1 d . . . H15A H 0.3142 0.3418 0.1633 0.095 Uiso 1 1 calc R . . H15B H 0.2426 0.2866 0.0528 0.095 Uiso 1 1 calc R . . H15C H 0.2372 0.4045 0.1931 0.095 Uiso 1 1 calc R . . C16 C 0.4432(2) 1.1143(3) 0.2061(5) 0.0594(8) Uani 1 1 d . . . H16A H 0.4596 1.0847 0.1061 0.089 Uiso 1 1 calc R . . H16B H 0.4786 1.1826 0.2646 0.089 Uiso 1 1 calc R . . H16C H 0.3966 1.1656 0.1832 0.089 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 Br1 0.04502(16) 0.0795(2) 0.0931(3) -0.0090(2) -0.00077(13) -0.0074(2) O1 0.0581(12) 0.0464(11) 0.0392(9) -0.0094(8) 0.0034(9) -0.0097(8) O2 0.0604(13) 0.0438(11) 0.0428(10) -0.0089(8) 0.0000(9) -0.0098(9) C1 0.0460(13) 0.0335(12) 0.0284(10) -0.0018(9) 0.0036(9) -0.0002(10) C2 0.0397(13) 0.0404(12) 0.0271(11) 0.0048(10) 0.0041(9) 0.0018(10) C3 0.0403(13) 0.0485(15) 0.0418(14) 0.0053(11) 0.0075(11) 0.0019(11) C4 0.0506(17) 0.0632(18) 0.0513(16) 0.0102(13) 0.0175(14) 0.0170(13) C5 0.069(2) 0.0569(19) 0.0518(17) 0.0006(15) 0.0241(16) 0.0209(15) C6 0.0628(17) 0.0414(15) 0.0380(14) -0.0037(11) 0.0148(13) 0.0059(12) C7 0.0471(14) 0.0338(12) 0.0303(11) 0.0011(9) 0.0072(10) 0.0036(10) C8 0.0468(14) 0.0368(13) 0.0304(11) -0.0003(9) 0.0015(10) -0.0008(10) C9 0.0409(13) 0.0392(13) 0.0315(11) 0.0022(9) 0.0029(10) 0.0039(10) C10 0.0425(14) 0.0551(16) 0.0433(16) 0.0048(12) 0.0042(12) 0.0024(12) C11 0.0429(15) 0.071(2) 0.0553(17) 0.0087(15) 0.0132(13) 0.0160(14) C12 0.0636(19) 0.0558(18) 0.0555(18) -0.0026(14) 0.0179(15) 0.0209(15) C13 0.0553(16) 0.0439(15) 0.0431(14) -0.0054(11) 0.0092(12) 0.0125(12) C14 0.0438(13) 0.0372(13) 0.0286(11) 0.0009(10) 0.0049(9) 0.0058(10) C15 0.077(3) 0.0377(16) 0.073(2) -0.0010(14) 0.0031(18) -0.0085(13) C16 0.078(2) 0.0422(17) 0.0597(18) -0.0062(13) 0.0147(17) -0.0144(14) _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 Br1 C3 1.903(3) . ? O1 C1 1.370(3) . ? O1 C15 1.436(4) . ? O2 C8 1.373(3) . ? O2 C16 1.438(4) . ? C1 C14 1.402(4) . ? C1 C2 1.407(3) . ? C2 C3 1.436(4) . ? C2 C7 1.445(4) . ? C3 C4 1.361(4) . ? C4 C5 1.410(5) . ? C4 H4 0.9300 . ? C5 C6 1.344(5) . ? C5 H5 0.9300 . ? C6 C7 1.434(4) . ? C6 H6 0.9300 . ? C7 C8 1.397(4) . ? C8 C9 1.390(4) . ? C9 C10 1.424(4) . ? C9 C14 1.429(4) . ? C10 C11 1.364(4) . ? C10 H10 0.9300 . ? C11 C12 1.405(5) . ? C11 H11 0.9300 . ? C12 C13 1.350(5) . ? C12 H12 0.9300 . ? C13 C14 1.439(3) . ? C13 H13 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? 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 C1 O1 C15 113.6(2) . . ? C8 O2 C16 114.4(2) . . ? O1 C1 C14 116.9(2) . . ? O1 C1 C2 121.5(2) . . ? C14 C1 C2 121.6(2) . . ? C1 C2 C3 126.1(2) . . ? C1 C2 C7 117.7(2) . . ? C3 C2 C7 116.2(2) . . ? C4 C3 C2 122.0(3) . . ? C4 C3 Br1 114.6(2) . . ? C2 C3 Br1 123.20(19) . . ? C3 C4 C5 120.4(3) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C6 C5 C4 120.9(3) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C7 120.8(3) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C8 C7 C6 120.4(2) . . ? C8 C7 C2 120.1(2) . . ? C6 C7 C2 119.5(3) . . ? O2 C8 C9 119.2(3) . . ? O2 C8 C7 119.0(2) . . ? C9 C8 C7 121.7(2) . . ? C8 C9 C10 122.4(3) . . ? C8 C9 C14 118.8(2) . . ? C10 C9 C14 118.7(2) . . ? C11 C10 C9 120.7(3) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C10 C11 C12 120.5(3) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C13 C12 C11 121.2(3) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C14 120.5(3) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C1 C14 C9 119.9(2) . . ? C1 C14 C13 121.8(2) . . ? C9 C14 C13 118.3(3) . . ? O1 C15 H15A 109.5 . . ? O1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O2 C16 H16A 109.5 . . ? O2 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O2 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 O1 C1 C14 93.4(3) . . . . ? C15 O1 C1 C2 -87.5(3) . . . . ? O1 C1 C2 C3 -3.9(4) . . . . ? C14 C1 C2 C3 175.2(2) . . . . ? O1 C1 C2 C7 176.7(2) . . . . ? C14 C1 C2 C7 -4.2(3) . . . . ? C1 C2 C3 C4 176.2(3) . . . . ? C7 C2 C3 C4 -4.3(4) . . . . ? C1 C2 C3 Br1 -9.4(3) . . . . ? C7 C2 C3 Br1 170.05(18) . . . . ? C2 C3 C4 C5 1.8(4) . . . . ? Br1 C3 C4 C5 -173.0(2) . . . . ? C3 C4 C5 C6 1.2(4) . . . . ? C4 C5 C6 C7 -1.4(4) . . . . ? C5 C6 C7 C8 178.2(3) . . . . ? C5 C6 C7 C2 -1.3(4) . . . . ? C1 C2 C7 C8 4.1(3) . . . . ? C3 C2 C7 C8 -175.4(2) . . . . ? C1 C2 C7 C6 -176.5(2) . . . . ? C3 C2 C7 C6 4.0(3) . . . . ? C16 O2 C8 C9 90.7(3) . . . . ? C16 O2 C8 C7 -91.7(3) . . . . ? C6 C7 C8 O2 2.0(4) . . . . ? C2 C7 C8 O2 -178.6(2) . . . . ? C6 C7 C8 C9 179.5(2) . . . . ? C2 C7 C8 C9 -1.0(4) . . . . ? O2 C8 C9 C10 -2.8(4) . . . . ? C7 C8 C9 C10 179.6(2) . . . . ? O2 C8 C9 C14 175.6(2) . . . . ? C7 C8 C9 C14 -1.9(4) . . . . ? C8 C9 C10 C11 178.5(3) . . . . ? C14 C9 C10 C11 0.1(4) . . . . ? C9 C10 C11 C12 0.2(5) . . . . ? C10 C11 C12 C13 -0.4(5) . . . . ? C11 C12 C13 C14 0.4(5) . . . . ? O1 C1 C14 C9 -179.5(2) . . . . ? C2 C1 C14 C9 1.3(3) . . . . ? O1 C1 C14 C13 0.9(3) . . . . ? C2 C1 C14 C13 -178.2(2) . . . . ? C8 C9 C14 C1 1.8(4) . . . . ? C10 C9 C14 C1 -179.7(2) . . . . ? C8 C9 C14 C13 -178.6(2) . . . . ? C10 C9 C14 C13 -0.1(3) . . . . ? C12 C13 C14 C1 179.5(3) . . . . ? C12 C13 C14 C9 -0.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.04 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.343 _refine_diff_density_min -0.191 _refine_diff_density_rms 0.059