data_cd213302 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H19 Br O4' _chemical_formula_weight 415.27 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' '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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.5559(16) _cell_length_b 6.3280(9) _cell_length_c 13.4204(18) _cell_angle_alpha 90.00 _cell_angle_beta 96.817(3) _cell_angle_gamma 90.00 _cell_volume 974.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2121 _cell_measurement_theta_min 6.115 _cell_measurement_theta_max 44.704 _exptl_crystal_description prismatic _exptl_crystal_colour green _exptl_crystal_size_max 0.211 _exptl_crystal_size_mid 0.154 _exptl_crystal_size_min 0.113 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 2.131 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.0893 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 5842 _diffrn_reflns_av_R_equivalents 0.0374 _diffrn_reflns_av_sigmaI/netI 0.0703 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3448 _reflns_number_gt 2733 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0646P)^2^+0.0569P] 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 SHELXL _refine_ls_extinction_coef 0.012(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.005(13) _chemical_absolute_configuration ad _refine_ls_number_reflns 3448 _refine_ls_number_parameters 238 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0596 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.1317 _refine_ls_wR_factor_gt 0.1255 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.058 _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 Br1 Br 0.63470(4) 0.78282(13) -0.20117(3) 0.0835(3) Uani 1 1 d . . . O1 O 0.8139(3) 1.1724(5) 0.3296(3) 0.0732(10) Uani 1 1 d . . . O2 O 0.6445(3) 1.0459(5) 0.3506(2) 0.0566(8) Uani 1 1 d . . . O3 O 0.4469(3) 1.0920(7) 0.4380(3) 0.0773(11) Uani 1 1 d . . . O4 O 0.3785(3) 0.7883(9) 0.3682(2) 0.0761(9) Uani 1 1 d . . . C1 C 0.7549(4) 1.0193(7) 0.3275(3) 0.0517(11) Uani 1 1 d . . . C2 C 0.7954(3) 0.7939(8) 0.3126(3) 0.0437(8) Uani 1 1 d . . . C3 C 0.6955(3) 0.6586(6) 0.2576(3) 0.0442(9) Uani 1 1 d . . . H3 H 0.7159 0.5098 0.2698 0.053 Uiso 1 1 calc R . . C4 C 0.5846(4) 0.7002(8) 0.3027(3) 0.0505(11) Uani 1 1 d . . . H4 H 0.5283 0.5948 0.3007 0.061 Uiso 1 1 calc R . . C5 C 0.5657(4) 0.8797(7) 0.3444(3) 0.0484(10) Uani 1 1 d . . . C6 C 0.4594(4) 0.9393(9) 0.3902(3) 0.0596(12) Uani 1 1 d . . . C7 C 0.2709(5) 0.8191(16) 0.4102(5) 0.103(2) Uani 1 1 d . . . H7A H 0.2832 0.7939 0.4812 0.155 Uiso 1 1 calc R . . H7B H 0.2133 0.7224 0.3795 0.155 Uiso 1 1 calc R . . H7C H 0.2444 0.9615 0.3979 0.155 Uiso 1 1 calc R . . C8 C 0.9001(3) 0.7779(9) 0.2536(3) 0.0515(9) Uani 1 1 d . . . C9 C 0.9628(4) 0.5895(8) 0.2583(4) 0.0594(12) Uani 1 1 d . . . H9 H 0.9443 0.4852 0.3027 0.071 Uiso 1 1 calc R . . C10 C 1.0505(5) 0.5514(10) 0.2005(5) 0.0775(16) Uani 1 1 d . . . H10 H 1.0919 0.4252 0.2065 0.093 Uiso 1 1 calc R . . C11 C 1.0761(6) 0.7043(12) 0.1333(7) 0.099(2) Uani 1 1 d . . . H11 H 1.1324 0.6784 0.0907 0.119 Uiso 1 1 calc R . . C12 C 1.0190(6) 0.8934(13) 0.1290(6) 0.100(2) Uani 1 1 d . . . H12 H 1.0406 0.9995 0.0869 0.120 Uiso 1 1 calc R . . C13 C 0.9295(5) 0.9287(9) 0.1864(5) 0.0763(16) Uani 1 1 d . . . H13 H 0.8885 1.0554 0.1798 0.092 Uiso 1 1 calc R . . C14 C 0.6758(3) 0.6907(7) 0.1452(3) 0.0443(9) Uani 1 1 d . . . C15 C 0.7121(4) 0.5368(8) 0.0821(4) 0.0584(11) Uani 1 1 d . . . H15 H 0.7456 0.4129 0.1094 0.070 Uiso 1 1 calc R . . C16 C 0.6994(4) 0.5651(9) -0.0199(4) 0.0621(12) Uani 1 1 d . . . H16 H 0.7238 0.4607 -0.0615 0.074 Uiso 1 1 calc R . . C17 C 0.6507(3) 0.7468(8) -0.0600(3) 0.0564(12) Uani 1 1 d . . . C18 C 0.6129(4) 0.9004(8) -0.0001(4) 0.0601(11) Uani 1 1 d . . . H18 H 0.5802 1.0245 -0.0279 0.072 Uiso 1 1 calc R . . C19 C 0.6240(4) 0.8680(7) 0.1020(4) 0.0566(11) Uani 1 1 d . . . H19 H 0.5954 0.9697 0.1428 0.068 Uiso 1 1 calc R . . C20 C 0.8221(4) 0.7078(7) 0.4215(3) 0.0517(10) Uani 1 1 d . . . H20A H 0.7517 0.7174 0.4541 0.062 Uiso 1 1 calc R . . H20B H 0.8424 0.5594 0.4181 0.062 Uiso 1 1 calc R . . C21 C 0.9192(4) 0.8210(9) 0.4857(4) 0.0723(14) Uani 1 1 d . . . H21A H 0.9893 0.8144 0.4538 0.108 Uiso 1 1 calc R . . H21B H 0.9323 0.7544 0.5503 0.108 Uiso 1 1 calc R . . H21C H 0.8978 0.9661 0.4937 0.108 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 0.0833(4) 0.1104(5) 0.0552(3) 0.0052(3) 0.0019(2) 0.0139(4) O1 0.065(2) 0.0306(15) 0.123(3) 0.0022(18) 0.0092(19) -0.0084(15) O2 0.0477(17) 0.0442(17) 0.077(2) -0.0063(15) 0.0050(14) 0.0052(13) O3 0.075(2) 0.087(3) 0.070(2) -0.030(2) 0.0122(18) 0.005(2) O4 0.0549(17) 0.099(3) 0.0777(19) -0.028(3) 0.0210(14) -0.013(2) C1 0.046(2) 0.036(2) 0.070(3) 0.008(2) -0.0030(19) 0.000(2) C2 0.0391(17) 0.0303(18) 0.0593(19) 0.000(2) -0.0041(14) -0.0050(19) C3 0.043(2) 0.033(2) 0.055(2) -0.0003(18) 0.0017(17) -0.0008(17) C4 0.043(2) 0.052(3) 0.055(3) -0.005(2) 0.0001(17) -0.0102(19) C5 0.043(2) 0.048(2) 0.053(2) -0.005(2) -0.0007(17) -0.0048(19) C6 0.054(3) 0.077(4) 0.046(2) -0.005(2) -0.0005(19) 0.006(2) C7 0.064(3) 0.141(7) 0.112(4) -0.042(5) 0.043(3) -0.025(4) C8 0.0406(19) 0.044(2) 0.068(2) 0.004(3) -0.0002(16) -0.009(2) C9 0.045(2) 0.049(3) 0.085(3) 0.014(2) 0.009(2) -0.002(2) C10 0.055(3) 0.060(3) 0.120(5) 0.000(3) 0.021(3) 0.004(2) C11 0.074(4) 0.096(5) 0.137(6) 0.012(4) 0.053(4) -0.002(4) C12 0.097(5) 0.089(5) 0.124(6) 0.047(4) 0.049(4) -0.003(4) C13 0.082(4) 0.051(3) 0.100(4) 0.024(3) 0.028(3) -0.001(3) C14 0.039(2) 0.038(2) 0.055(2) -0.0016(18) 0.0025(17) 0.0029(17) C15 0.062(3) 0.050(3) 0.062(3) 0.000(2) 0.002(2) 0.012(2) C16 0.060(3) 0.063(3) 0.063(3) -0.009(2) 0.009(2) 0.016(2) C17 0.047(2) 0.068(4) 0.052(2) 0.007(2) -0.0015(16) 0.007(2) C18 0.058(3) 0.052(3) 0.068(3) 0.002(2) -0.003(2) 0.015(2) C19 0.061(3) 0.050(3) 0.058(3) -0.002(2) 0.004(2) 0.010(2) C20 0.054(2) 0.040(2) 0.058(2) 0.0038(18) -0.0036(18) 0.0003(18) C21 0.073(3) 0.059(3) 0.076(3) -0.010(3) -0.026(2) 0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C17 1.895(4) . ? O1 C1 1.183(5) . ? O2 C1 1.359(5) . ? O2 C5 1.387(6) . ? O3 C6 1.178(6) . ? O4 C6 1.345(7) . ? O4 C7 1.437(6) . ? C1 C2 1.522(6) . ? C2 C8 1.527(5) . ? C2 C3 1.552(5) . ? C2 C20 1.555(6) . ? C3 C4 1.504(6) . ? C3 C14 1.513(6) . ? C3 H3 0.9800 . ? C4 C5 1.296(6) . ? C4 H4 0.9300 . ? C5 C6 1.486(7) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C13 1.383(7) . ? C8 C9 1.392(7) . ? C9 C10 1.369(7) . ? C9 H9 0.9300 . ? C10 C11 1.379(9) . ? C10 H10 0.9300 . ? C11 C12 1.365(10) . ? C11 H11 0.9300 . ? C12 C13 1.379(9) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C19 1.368(6) . ? C14 C15 1.388(6) . ? C15 C16 1.370(6) . ? C15 H15 0.9300 . ? C16 C17 1.363(7) . ? C16 H16 0.9300 . ? C17 C18 1.365(7) . ? C18 C19 1.377(7) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.512(6) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 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 O2 C5 121.3(3) . . ? C6 O4 C7 115.4(5) . . ? O1 C1 O2 116.6(4) . . ? O1 C1 C2 125.8(4) . . ? O2 C1 C2 117.2(3) . . ? C1 C2 C8 113.9(4) . . ? C1 C2 C3 110.9(3) . . ? C8 C2 C3 107.9(3) . . ? C1 C2 C20 103.6(3) . . ? C8 C2 C20 112.5(3) . . ? C3 C2 C20 107.9(3) . . ? C4 C3 C14 110.1(3) . . ? C4 C3 C2 109.5(3) . . ? C14 C3 C2 114.6(3) . . ? C4 C3 H3 107.5 . . ? C14 C3 H3 107.5 . . ? C2 C3 H3 107.5 . . ? C5 C4 C3 121.5(4) . . ? C5 C4 H4 119.2 . . ? C3 C4 H4 119.2 . . ? C4 C5 O2 123.2(4) . . ? C4 C5 C6 126.2(4) . . ? O2 C5 C6 110.6(4) . . ? O3 C6 O4 125.1(5) . . ? O3 C6 C5 126.5(5) . . ? O4 C6 C5 108.4(4) . . ? O4 C7 H7A 109.5 . . ? O4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C13 C8 C9 117.0(4) . . ? C13 C8 C2 124.3(5) . . ? C9 C8 C2 118.3(4) . . ? C10 C9 C8 122.7(5) . . ? C10 C9 H9 118.6 . . ? C8 C9 H9 118.6 . . ? C9 C10 C11 118.6(5) . . ? C9 C10 H10 120.7 . . ? C11 C10 H10 120.7 . . ? C12 C11 C10 120.2(6) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 120.6(6) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C12 C13 C8 120.7(5) . . ? C12 C13 H13 119.6 . . ? C8 C13 H13 119.6 . . ? C19 C14 C15 117.8(4) . . ? C19 C14 C3 122.6(4) . . ? C15 C14 C3 119.6(4) . . ? C16 C15 C14 120.9(4) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C17 C16 C15 119.7(5) . . ? C17 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? C16 C17 C18 120.9(4) . . ? C16 C17 Br1 118.9(4) . . ? C18 C17 Br1 120.2(4) . . ? C17 C18 C19 118.8(4) . . ? C17 C18 H18 120.6 . . ? C19 C18 H18 120.6 . . ? C14 C19 C18 121.9(4) . . ? C14 C19 H19 119.1 . . ? C18 C19 H19 119.1 . . ? C21 C20 C2 114.9(4) . . ? C21 C20 H20A 108.5 . . ? C2 C20 H20A 108.5 . . ? C21 C20 H20B 108.5 . . ? C2 C20 H20B 108.5 . . ? H20A C20 H20B 107.5 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 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 C5 O2 C1 O1 176.0(4) . . . . ? C5 O2 C1 C2 -10.4(6) . . . . ? O1 C1 C2 C8 -26.9(6) . . . . ? O2 C1 C2 C8 160.2(3) . . . . ? O1 C1 C2 C3 -148.8(5) . . . . ? O2 C1 C2 C3 38.2(5) . . . . ? O1 C1 C2 C20 95.6(5) . . . . ? O2 C1 C2 C20 -77.3(4) . . . . ? C1 C2 C3 C4 -44.7(4) . . . . ? C8 C2 C3 C4 -170.1(4) . . . . ? C20 C2 C3 C4 68.1(4) . . . . ? C1 C2 C3 C14 79.4(4) . . . . ? C8 C2 C3 C14 -45.9(5) . . . . ? C20 C2 C3 C14 -167.7(3) . . . . ? C14 C3 C4 C5 -98.6(5) . . . . ? C2 C3 C4 C5 28.1(6) . . . . ? C3 C4 C5 O2 0.3(7) . . . . ? C3 C4 C5 C6 179.3(4) . . . . ? C1 O2 C5 C4 -10.8(6) . . . . ? C1 O2 C5 C6 170.0(4) . . . . ? C7 O4 C6 O3 -1.9(8) . . . . ? C7 O4 C6 C5 178.0(5) . . . . ? C4 C5 C6 O3 170.8(5) . . . . ? O2 C5 C6 O3 -10.1(7) . . . . ? C4 C5 C6 O4 -9.1(6) . . . . ? O2 C5 C6 O4 170.0(4) . . . . ? C1 C2 C8 C13 -24.5(6) . . . . ? C3 C2 C8 C13 99.1(6) . . . . ? C20 C2 C8 C13 -142.1(5) . . . . ? C1 C2 C8 C9 163.2(4) . . . . ? C3 C2 C8 C9 -73.2(5) . . . . ? C20 C2 C8 C9 45.7(5) . . . . ? C13 C8 C9 C10 0.4(8) . . . . ? C2 C8 C9 C10 173.2(5) . . . . ? C8 C9 C10 C11 -1.4(9) . . . . ? C9 C10 C11 C12 3.5(11) . . . . ? C10 C11 C12 C13 -4.7(13) . . . . ? C11 C12 C13 C8 3.7(12) . . . . ? C9 C8 C13 C12 -1.5(9) . . . . ? C2 C8 C13 C12 -173.9(6) . . . . ? C4 C3 C14 C19 49.9(5) . . . . ? C2 C3 C14 C19 -73.9(5) . . . . ? C4 C3 C14 C15 -130.7(4) . . . . ? C2 C3 C14 C15 105.4(5) . . . . ? C19 C14 C15 C16 1.8(7) . . . . ? C3 C14 C15 C16 -177.6(4) . . . . ? C14 C15 C16 C17 0.2(7) . . . . ? C15 C16 C17 C18 -0.9(8) . . . . ? C15 C16 C17 Br1 179.7(4) . . . . ? C16 C17 C18 C19 -0.4(7) . . . . ? Br1 C17 C18 C19 178.9(4) . . . . ? C15 C14 C19 C18 -3.2(7) . . . . ? C3 C14 C19 C18 176.1(4) . . . . ? C17 C18 C19 C14 2.6(7) . . . . ? C1 C2 C20 C21 -63.1(4) . . . . ? C8 C2 C20 C21 60.4(5) . . . . ? C3 C2 C20 C21 179.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.518 _refine_diff_density_min -0.494 _refine_diff_density_rms 0.054