data_global _audit_creation_method 'APEX2 v2014.3-0' _publ_requested_journal ? _publ_contact_author_name ? _publ_contact_author_address ; ; _publ_contact_author_email ? _publ_contact_author_fax ? _publ_contact_author_phone ? _publ_section_title ; ; _publ_section_abstract ; ; _publ_section_references ; ; _publ_section_comment ; ; data_I _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H17 Br O4' _chemical_formula_iupac ? _chemical_formula_weight 401.24 _chemical_absolute_configuration ? _chemical_melting_point ? _space_group_crystal_system monoclinic _space_group_name_H-M_alt 'P 1 21 1' _space_group_name_Hall 'P 2yb' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.8349(3) _cell_length_b 7.3672(3) _cell_length_c 18.3255(8) _cell_angle_alpha 90 _cell_angle_beta 100.593(2) _cell_angle_gamma 90 _cell_volume 907.04(7) _cell_formula_units_Z 2 _cell_measurement_reflns_used 6433 _cell_measurement_theta_min 2.4529 _cell_measurement_theta_max 73.9477 _cell_measurement_temperature 200.(2) _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.453 _exptl_crystal_size_mid 0.371 _exptl_crystal_size_min 0.086 _exptl_crystal_density_diffrn 1.469 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 3.269 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2014/2 (Bruker AXS Inc.)' _exptl_absorpt_correction_T_min 0.46 _exptl_absorpt_correction_T_max 0.75 _exptl_special_details ; ; _diffrn_ambient_temperature 200.(2) _diffrn_source ? _diffrn_source_type ? _diffrn_radiation_type ? _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_monochromator ? _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.3333 _diffrn_reflns_number 19560 _diffrn_reflns_av_R_equivalents 0.0685 _diffrn_reflns_av_sigmaI/netI 0.0490 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 74.78 _diffrn_reflns_theta_full 74.78 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _refine_special_details ; ; _reflns_number_total 3698 _reflns_number_gt 3523 _reflns_threshold_expression 'I > 2\s(I)' _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_gt 0.1201 _refine_ls_wR_factor_ref 0.1214 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.114 _refine_ls_number_reflns 3698 _refine_ls_number_parameters 232 _refine_ls_number_restraints 1 _refine_ls_hydrogen_treatment mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0749P)^2^+0.0991P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.634 _refine_diff_density_min -0.412 _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_extinction_coef 0.0098(15) _refine_ls_abs_structure_details ; Flack x determined using 1495 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.01(3) 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' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _computing_data_collection ? _computing_cell_refinement 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_data_reduction 'SAINT V8.34A (Bruker AXS Inc., 2013)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_molecular_graphics ? _computing_publication_material ? loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_flags_posn _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C C1 0.6532(6) 0.4414(6) 0.3727(2) 0.0272(8) Uani d . . . 1 . . C C2 0.6327(6) 0.5490(7) 0.4422(3) 0.0307(9) Uani d . . . 1 . . C C3 0.7719(6) 0.7007(7) 0.4489(3) 0.0323(9) Uani d . . . 1 . . C C4 0.8755(6) 0.7012(6) 0.3940(3) 0.0297(9) Uani d . . . 1 . . C C5 0.8057(6) 0.5548(6) 0.3372(2) 0.0267(8) Uani d . . . 1 . . H H5 0.9214 0.4755 0.3325 0.032 Uiso calc U . R 1 . . C C6 0.4501(6) 0.4208(5) 0.3231(2) 0.0275(9) Uani d . . . 1 . . C C7 0.2662(8) 0.3247(8) 0.1448(3) 0.0439(12) Uani d . . . 1 . . H H7 0.3664 0.3974 0.1297 0.053 Uiso calc U . R 1 . . C C8 0.0970(10) 0.2723(11) 0.0937(4) 0.0590(16) Uani d . . . 1 . . H H8 0.0813 0.3088 0.0432 0.071 Uiso calc U . R 1 . . C C9 -0.0472(10) 0.1670(9) 0.1173(4) 0.0603(17) Uani d . . . 1 . . H H9 -0.1615 0.1304 0.0827 0.072 Uiso calc U . R 1 . . C C10 -0.0262(9) 0.1152(8) 0.1898(4) 0.0529(14) Uani d . . . 1 . . H H10 -0.1267 0.0438 0.2053 0.063 Uiso calc U . R 1 . . C C11 0.1402(8) 0.1658(7) 0.2409(3) 0.0427(11) Uani d . . . 1 . . H H11 0.1554 0.1306 0.2915 0.051 Uiso calc U . R 1 . . C C12 0.2838(6) 0.2695(6) 0.2160(3) 0.0325(9) Uani d . . . 1 . . C C13 0.7362(7) 0.2524(7) 0.3963(3) 0.0363(10) Uani d . . . 1 . . H H13A 0.6446 0.1894 0.4231 0.054 Uiso calc U . R 1 . . H H13B 0.8665 0.2648 0.4288 0.054 Uiso calc U . R 1 . . H H13C 0.7504 0.1822 0.3522 0.054 Uiso calc U . R 1 . . C C14 1.0427(7) 0.8248(7) 0.3861(3) 0.0396(11) Uani d . . . 1 . . H H14A 1.0351 0.9348 0.4156 0.059 Uiso calc U . R 1 . . H H14B 1.0334 0.8578 0.3338 0.059 Uiso calc U . R 1 . . H H14C 1.1696 0.7633 0.4039 0.059 Uiso calc U . R 1 . . C C15 0.8098(7) 0.5961(7) 0.2007(3) 0.0323(9) Uani d . . . 1 . . H H15 0.9211 0.5166 0.2067 0.039 Uiso calc U . R 1 . . C C16 0.7352(7) 0.6672(7) 0.1312(3) 0.0366(10) Uani d . . . 1 . . H H16 0.7945 0.6372 0.0897 0.044 Uiso calc U . R 1 . . C C17 0.5735(8) 0.7821(7) 0.1230(3) 0.0373(10) Uani d . . . 1 . . C C18 0.4866(8) 0.8301(7) 0.1825(3) 0.0386(11) Uani d . . . 1 . . H H18 0.3745 0.9086 0.1759 0.046 Uiso calc U . R 1 . . C C19 0.5658(7) 0.7619(7) 0.2520(3) 0.0350(10) Uani d . . . 1 . . H H19 0.5114 0.799 0.2937 0.042 Uiso calc U . R 1 . . C C20 0.7246(6) 0.6391(6) 0.2618(3) 0.0287(9) Uani d . . . 1 . . O O1 0.2980(5) 0.4896(6) 0.3333(2) 0.0438(9) Uani d . . . 1 . . O O2 0.4621(4) 0.3107(5) 0.26562(18) 0.0336(7) Uani d . . . 1 . . O O3 0.5286(5) 0.5081(6) 0.4871(2) 0.0436(9) Uani d . . . 1 . . O O4 0.8048(5) 0.8140(6) 0.5088(2) 0.0435(9) Uani d . . . 1 . . H H4 0.707(12) 0.853(12) 0.517(4) 0.065 Uiso d U . . 1 . . Br Br1 0.46638(10) 0.88088(9) 0.02817(3) 0.0548(3) Uani d . . . 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C1 0.0213(17) 0.031(2) 0.030(2) 0.0027(15) 0.0067(15) -0.0021(16) C2 0.0207(17) 0.042(2) 0.030(2) 0.0014(17) 0.0040(15) -0.0035(18) C3 0.0229(17) 0.038(2) 0.034(2) 0.0038(17) 0.0013(15) -0.0077(18) C4 0.0232(18) 0.032(2) 0.032(2) 0.0035(17) 0.0017(15) -0.0029(17) C5 0.0195(16) 0.0300(19) 0.031(2) -0.0009(15) 0.0060(14) -0.0042(16) C6 0.0227(17) 0.029(2) 0.031(2) -0.0002(14) 0.0061(15) -0.0028(15) C7 0.042(3) 0.052(3) 0.037(3) -0.003(2) 0.0061(19) -0.006(2) C8 0.062(4) 0.070(4) 0.040(3) -0.001(3) -0.006(3) -0.010(3) C9 0.048(3) 0.055(4) 0.070(4) -0.006(3) -0.011(3) -0.016(3) C10 0.040(3) 0.044(3) 0.068(4) -0.011(2) -0.006(2) -0.006(3) C11 0.041(3) 0.036(2) 0.049(3) -0.010(2) 0.002(2) 0.000(2) C12 0.0262(19) 0.032(2) 0.038(2) -0.0001(16) 0.0027(17) -0.0075(18) C13 0.031(2) 0.033(2) 0.044(3) 0.0054(18) 0.0037(18) 0.007(2) C14 0.032(2) 0.040(2) 0.047(3) -0.0082(19) 0.0083(19) -0.006(2) C15 0.032(2) 0.032(2) 0.034(2) 0.0034(17) 0.0088(17) -0.0037(18) C16 0.040(2) 0.037(2) 0.033(2) -0.002(2) 0.0081(18) -0.0024(19) C17 0.044(3) 0.033(2) 0.031(2) -0.0060(19) -0.0025(18) -0.0013(19) C18 0.036(2) 0.034(2) 0.044(3) 0.0051(17) 0.0020(19) 0.0022(18) C19 0.034(2) 0.036(2) 0.036(2) 0.0065(18) 0.0083(18) -0.0025(18) C20 0.0245(19) 0.029(2) 0.032(2) 0.0011(16) 0.0040(16) -0.0004(17) O1 0.0222(14) 0.057(2) 0.051(2) 0.0060(15) 0.0042(13) -0.0160(18) O2 0.0234(14) 0.0408(16) 0.0357(18) 0.0016(13) 0.0033(12) -0.0102(14) O3 0.0371(17) 0.063(2) 0.0340(18) -0.0076(16) 0.0139(14) -0.0061(17) O4 0.0277(15) 0.060(2) 0.042(2) 0.0012(15) 0.0033(13) -0.0231(17) Br1 0.0748(4) 0.0464(3) 0.0362(3) 0.0046(3) -0.0080(2) 0.0056(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 C6 . 1.520(6) ? C1 C2 . 1.527(6) ? C1 C13 . 1.536(6) ? C1 C5 . 1.568(5) ? C2 O3 . 1.222(5) ? C2 C3 . 1.458(7) ? C3 C4 . 1.332(6) ? C3 O4 . 1.365(6) ? C4 C14 . 1.489(6) ? C4 C5 . 1.514(6) ? C5 C20 . 1.523(6) ? C5 H5 . 1.0 ? C6 O1 . 1.202(5) ? C6 O2 . 1.344(5) ? C7 C12 . 1.351(7) ? C7 C8 . 1.402(8) ? C7 H7 . 0.95 ? C8 C9 . 1.385(11) ? C8 H8 . 0.95 ? C9 C10 . 1.364(10) ? C9 H9 . 0.95 ? C10 C11 . 1.385(8) ? C10 H10 . 0.95 ? C11 C12 . 1.386(7) ? C11 H11 . 0.95 ? C12 O2 . 1.413(5) ? C13 H13A . 0.98 ? C13 H13B . 0.98 ? C13 H13C . 0.98 ? C14 H14A . 0.98 ? C14 H14B . 0.98 ? C14 H14C . 0.98 ? C15 C16 . 1.385(7) ? C15 C20 . 1.391(6) ? C15 H15 . 0.95 ? C16 C17 . 1.378(7) ? C16 H16 . 0.95 ? C17 C18 . 1.381(7) ? C17 Br1 . 1.902(5) ? C18 C19 . 1.382(7) ? C18 H18 . 0.95 ? C19 C20 . 1.399(6) ? C19 H19 . 0.95 ? O4 H4 . 0.77(8) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C6 C1 C2 . . 109.7(3) ? C6 C1 C13 . . 109.1(4) ? C2 C1 C13 . . 108.8(4) ? C6 C1 C5 . . 114.1(4) ? C2 C1 C5 . . 103.9(3) ? C13 C1 C5 . . 111.1(3) ? O3 C2 C3 . . 125.7(5) ? O3 C2 C1 . . 126.0(5) ? C3 C2 C1 . . 108.0(3) ? C4 C3 O4 . . 125.1(4) ? C4 C3 C2 . . 111.6(4) ? O4 C3 C2 . . 123.0(4) ? C3 C4 C14 . . 126.8(4) ? C3 C4 C5 . . 111.9(4) ? C14 C4 C5 . . 121.3(4) ? C4 C5 C20 . . 110.5(4) ? C4 C5 C1 . . 104.1(3) ? C20 C5 C1 . . 115.8(3) ? C4 C5 H5 . . 108.8 ? C20 C5 H5 . . 108.8 ? C1 C5 H5 . . 108.8 ? O1 C6 O2 . . 123.8(4) ? O1 C6 C1 . . 125.8(4) ? O2 C6 C1 . . 110.4(3) ? C12 C7 C8 . . 118.6(5) ? C12 C7 H7 . . 120.7 ? C8 C7 H7 . . 120.7 ? C9 C8 C7 . . 119.5(6) ? C9 C8 H8 . . 120.3 ? C7 C8 H8 . . 120.3 ? C10 C9 C8 . . 120.5(6) ? C10 C9 H9 . . 119.7 ? C8 C9 H9 . . 119.7 ? C9 C10 C11 . . 120.7(6) ? C9 C10 H10 . . 119.7 ? C11 C10 H10 . . 119.7 ? C10 C11 C12 . . 117.9(6) ? C10 C11 H11 . . 121.0 ? C12 C11 H11 . . 121.0 ? C7 C12 C11 . . 122.8(5) ? C7 C12 O2 . . 118.0(4) ? C11 C12 O2 . . 119.0(5) ? C1 C13 H13A . . 109.5 ? C1 C13 H13B . . 109.5 ? H13A C13 H13B . . 109.5 ? C1 C13 H13C . . 109.5 ? H13A C13 H13C . . 109.5 ? H13B C13 H13C . . 109.5 ? C4 C14 H14A . . 109.5 ? C4 C14 H14B . . 109.5 ? H14A C14 H14B . . 109.5 ? C4 C14 H14C . . 109.5 ? H14A C14 H14C . . 109.5 ? H14B C14 H14C . . 109.5 ? C16 C15 C20 . . 121.1(4) ? C16 C15 H15 . . 119.5 ? C20 C15 H15 . . 119.5 ? C17 C16 C15 . . 119.0(4) ? C17 C16 H16 . . 120.5 ? C15 C16 H16 . . 120.5 ? C16 C17 C18 . . 121.6(5) ? C16 C17 Br1 . . 120.0(4) ? C18 C17 Br1 . . 118.3(4) ? C17 C18 C19 . . 118.8(5) ? C17 C18 H18 . . 120.6 ? C19 C18 H18 . . 120.6 ? C18 C19 C20 . . 121.1(4) ? C18 C19 H19 . . 119.4 ? C20 C19 H19 . . 119.4 ? C15 C20 C19 . . 118.3(4) ? C15 C20 C5 . . 120.1(4) ? C19 C20 C5 . . 121.7(4) ? C6 O2 C12 . . 117.7(3) ? C3 O4 H4 . . 111.(6) ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C6 C1 C2 O3 . . . . 58.3(6) ? C13 C1 C2 O3 . . . . -60.9(6) ? C5 C1 C2 O3 . . . . -179.4(5) ? C6 C1 C2 C3 . . . . -126.5(4) ? C13 C1 C2 C3 . . . . 114.3(4) ? C5 C1 C2 C3 . . . . -4.2(5) ? O3 C2 C3 C4 . . . . 174.9(5) ? C1 C2 C3 C4 . . . . -0.3(5) ? O3 C2 C3 O4 . . . . 1.6(8) ? C1 C2 C3 O4 . . . . -173.7(4) ? O4 C3 C4 C14 . . . . -1.1(8) ? C2 C3 C4 C14 . . . . -174.2(4) ? O4 C3 C4 C5 . . . . 178.2(4) ? C2 C3 C4 C5 . . . . 5.1(6) ? C3 C4 C5 C20 . . . . 117.4(4) ? C14 C4 C5 C20 . . . . -63.2(5) ? C3 C4 C5 C1 . . . . -7.5(5) ? C14 C4 C5 C1 . . . . 171.9(4) ? C6 C1 C5 C4 . . . . 126.0(4) ? C2 C1 C5 C4 . . . . 6.7(4) ? C13 C1 C5 C4 . . . . -110.1(4) ? C6 C1 C5 C20 . . . . 4.6(5) ? C2 C1 C5 C20 . . . . -114.8(4) ? C13 C1 C5 C20 . . . . 128.4(4) ? C2 C1 C6 O1 . . . . 5.3(6) ? C13 C1 C6 O1 . . . . 124.4(5) ? C5 C1 C6 O1 . . . . -110.7(5) ? C2 C1 C6 O2 . . . . -173.6(4) ? C13 C1 C6 O2 . . . . -54.6(4) ? C5 C1 C6 O2 . . . . 70.4(4) ? C12 C7 C8 C9 . . . . 0.3(9) ? C7 C8 C9 C10 . . . . 0.5(10) ? C8 C9 C10 C11 . . . . -0.5(10) ? C9 C10 C11 C12 . . . . -0.2(9) ? C8 C7 C12 C11 . . . . -1.1(8) ? C8 C7 C12 O2 . . . . 175.0(5) ? C10 C11 C12 C7 . . . . 1.0(8) ? C10 C11 C12 O2 . . . . -175.0(5) ? C20 C15 C16 C17 . . . . -0.1(7) ? C15 C16 C17 C18 . . . . 1.1(7) ? C15 C16 C17 Br1 . . . . -179.6(4) ? C16 C17 C18 C19 . . . . 0.6(8) ? Br1 C17 C18 C19 . . . . -178.8(4) ? C17 C18 C19 C20 . . . . -3.2(8) ? C16 C15 C20 C19 . . . . -2.4(7) ? C16 C15 C20 C5 . . . . 178.2(4) ? C18 C19 C20 C15 . . . . 4.1(7) ? C18 C19 C20 C5 . . . . -176.6(4) ? C4 C5 C20 C15 . . . . 120.8(4) ? C1 C5 C20 C15 . . . . -121.3(4) ? C4 C5 C20 C19 . . . . -58.5(5) ? C1 C5 C20 C19 . . . . 59.4(5) ? O1 C6 O2 C12 . . . . -2.1(7) ? C1 C6 O2 C12 . . . . 176.8(4) ? C7 C12 O2 C6 . . . . 116.6(5) ? C11 C12 O2 C6 . . . . -67.2(6) ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O4 H4 O3 2_656 0.77(8) 1.96(8) 2.703(5) 162.(8) ?