 
data_sad 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety        'C14 H11 Br O4'
_chemical_formula_sum 
 'C14 H11 Br O4' 
_chemical_formula_weight          323.14 
 
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    'P 21/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                    19.6704(7) 
_cell_length_b                    4.7195(2) 
_cell_length_c                    14.9893(5) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  112.153(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      1288.80(9) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     120(2) 
_cell_measurement_reflns_used     3146 
_cell_measurement_theta_min       2.91 
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        Block
_exptl_crystal_colour             Yellow 
_exptl_crystal_size_max           0.08 
_exptl_crystal_size_mid           0.04 
_exptl_crystal_size_min           0.03 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.665 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              648 
_exptl_absorpt_coefficient_mu     3.196 
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.7841 
_exptl_absorpt_correction_T_max   0.9102 
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)' 
 
_exptl_special_details 
; 
SADABS was used to perform the Absorption correction 
Parameter refinement on 9778 reflections reduced R(int) from 0.0685  to 0.0458 
Ratio of minimum to maximum apparent transmission: 0.828414 
The given Tmin and Tmax were generated using the SHELX SIZE command
; 
 
_diffrn_ambient_temperature       120(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-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   '4096x4096pixels / 62x62mm'
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             10921 
_diffrn_reflns_av_R_equivalents   0.0468 
_diffrn_reflns_av_sigmaI/netI     0.0463 
_diffrn_reflns_limit_h_min        -25 
_diffrn_reflns_limit_h_max        25 
_diffrn_reflns_limit_k_min        -6 
_diffrn_reflns_limit_k_max        6 
_diffrn_reflns_limit_l_min        -19 
_diffrn_reflns_limit_l_max        19 
_diffrn_reflns_theta_min          2.93 
_diffrn_reflns_theta_max          27.48 
_reflns_number_total              2939 
_reflns_number_gt                 2399 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)' 
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0000P)²+3.3874P] where P=(Fo²+2Fc²)/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          2939 
_refine_ls_number_parameters      173 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0625 
_refine_ls_R_factor_gt            0.0444 
_refine_ls_wR_factor_ref          0.0918 
_refine_ls_wR_factor_gt           0.0828 
_refine_ls_goodness_of_fit_ref    1.133 
_refine_ls_restrained_S_all       1.133 
_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 
C1 C 0.20922(18) 0.3207(7) 0.1303(2) 0.0197(7) Uani 1 1 d . . . 
C2 C 0.25208(17) 0.3234(7) 0.2245(2) 0.0189(7) Uani 1 1 d . . . 
C3 C 0.23430(17) 0.5206(7) 0.2902(2) 0.0176(7) Uani 1 1 d . . . 
C4 C 0.16728(17) 0.6974(7) 0.2511(2) 0.0185(7) Uani 1 1 d . . . 
C5 C 0.12172(17) 0.6793(7) 0.1539(2) 0.0186(7) Uani 1 1 d . . . 
C6 C 0.14022(18) 0.4878(7) 0.0876(2) 0.0210(7) Uani 1 1 d . . . 
C7 C 0.14976(19) 0.8830(7) 0.3118(2) 0.0231(7) Uani 1 1 d . . . 
H7 H 0.1806 0.8952 0.3780 0.028 Uiso 1 1 calc R . . 
C8 C 0.0873(2) 1.0490(7) 0.2751(3) 0.0268(8) Uani 1 1 d . . . 
H8 H 0.0756 1.1768 0.3161 0.032 Uiso 1 1 calc R . . 
C9 C 0.0416(2) 1.0295(8) 0.1784(3) 0.0272(8) Uani 1 1 d . . . 
H9 H -0.0013 1.1436 0.1537 0.033 Uiso 1 1 calc R . . 
C10 C 0.05845(19) 0.8439(7) 0.1179(3) 0.0251(8) Uani 1 1 d . . . 
H10 H 0.0269 0.8292 0.0520 0.030 Uiso 1 1 calc R . . 
C11 C 0.32124(18) 0.1530(7) 0.2704(2) 0.0222(7) Uani 1 1 d . . . 
H11A H 0.3208 -0.0096 0.2285 0.027 Uiso 1 1 calc R . . 
H11B H 0.3233 0.0773 0.3330 0.027 Uiso 1 1 calc R . . 
C12 C 0.38834(19) 0.3339(7) 0.2862(3) 0.0243(7) Uani 1 1 d . . . 
C13 C 0.51634(19) 0.3703(9) 0.3717(3) 0.0359(9) Uani 1 1 d . . . 
H13A H 0.5119 0.5668 0.3919 0.043 Uiso 1 1 calc R . . 
H13B H 0.5285 0.3772 0.3134 0.043 Uiso 1 1 calc R . . 
C14 C 0.5748(2) 0.2143(12) 0.4510(3) 0.0496(12) Uani 1 1 d . . . 
H14A H 0.5608 0.2001 0.5070 0.074 Uiso 1 1 calc R . . 
H14B H 0.6214 0.3171 0.4691 0.074 Uiso 1 1 calc R . . 
H14C H 0.5805 0.0237 0.4288 0.074 Uiso 1 1 calc R . . 
O1 O 0.10120(14) 0.4699(5) 0.00245(17) 0.0286(6) Uani 1 1 d . . . 
O2 O 0.27536(13) 0.5342(5) 0.37438(16) 0.0268(6) Uani 1 1 d . . . 
O3 O 0.38798(14) 0.5505(5) 0.2442(2) 0.0364(7) Uani 1 1 d . . . 
O4 O 0.44782(13) 0.2164(5) 0.35168(18) 0.0284(6) Uani 1 1 d . . . 
Br1 Br 0.23295(2) 0.10460(8) 0.04023(3) 0.02918(12) Uani 1 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 
C1 0.0211(16) 0.0195(16) 0.0212(16) -0.0012(13) 0.0112(14) -0.0013(13) 
C2 0.0187(16) 0.0188(16) 0.0199(16) 0.0019(13) 0.0081(13) -0.0031(13) 
C3 0.0167(15) 0.0205(16) 0.0151(15) 0.0027(12) 0.0055(13) -0.0048(13) 
C4 0.0201(16) 0.0163(15) 0.0198(16) 0.0021(13) 0.0083(13) -0.0035(13) 
C5 0.0187(16) 0.0186(16) 0.0188(16) 0.0038(13) 0.0075(13) -0.0027(13) 
C6 0.0221(17) 0.0208(16) 0.0203(17) 0.0005(13) 0.0082(14) -0.0060(14) 
C7 0.0292(18) 0.0207(16) 0.0217(16) 0.0003(14) 0.0122(14) -0.0035(15) 
C8 0.037(2) 0.0204(18) 0.034(2) 0.0012(15) 0.0266(18) -0.0011(15) 
C9 0.0250(18) 0.0250(18) 0.035(2) 0.0081(16) 0.0151(16) 0.0047(15) 
C10 0.0232(17) 0.0269(19) 0.0243(17) 0.0068(15) 0.0081(14) 0.0010(15) 
C11 0.0225(17) 0.0189(17) 0.0242(17) 0.0041(14) 0.0077(14) 0.0029(14) 
C12 0.0247(18) 0.0230(18) 0.0283(18) -0.0017(15) 0.0133(15) 0.0030(14) 
C13 0.0212(18) 0.039(2) 0.048(2) -0.011(2) 0.0131(17) -0.0074(18) 
C14 0.023(2) 0.082(4) 0.036(2) -0.001(2) 0.0020(18) -0.011(2) 
O1 0.0296(14) 0.0349(14) 0.0169(12) -0.0013(11) 0.0040(11) -0.0023(11) 
O2 0.0266(13) 0.0345(14) 0.0171(12) 0.0004(10) 0.0058(10) -0.0036(11) 
O3 0.0288(14) 0.0276(15) 0.0577(18) 0.0125(13) 0.0220(14) 0.0022(12) 
O4 0.0185(12) 0.0310(14) 0.0335(14) 0.0007(11) 0.0071(11) -0.0035(11) 
Br1 0.0376(2) 0.02839(19) 0.02558(19) -0.00458(16) 0.01647(16) 0.00279(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 
C1 C2 1.343(4) . ? 
C1 C6 1.490(5) . ? 
C1 Br1 1.886(3) . ? 
C2 C3 1.490(4) . ? 
C2 C11 1.505(4) . ? 
C3 O2 1.216(4) . ? 
C3 C4 1.482(4) . ? 
C4 C5 1.396(4) . ? 
C4 C7 1.396(5) . ? 
C5 C10 1.392(5) . ? 
C5 C6 1.487(5) . ? 
C6 O1 1.219(4) . ? 
C7 C8 1.385(5) . ? 
C7 H7 0.9500 . ? 
C8 C9 1.390(5) . ? 
C8 H8 0.9500 . ? 
C9 C10 1.388(5) . ? 
C9 H9 0.9500 . ? 
C10 H10 0.9500 . ? 
C11 C12 1.514(5) . ? 
C11 H11A 0.9900 . ? 
C11 H11B 0.9900 . ? 
C12 O3 1.199(4) . ? 
C12 O4 1.332(4) . ? 
C13 O4 1.459(4) . ? 
C13 C14 1.499(6) . ? 
C13 H13A 0.9900 . ? 
C13 H13B 0.9900 . ? 
C14 H14A 0.9800 . ? 
C14 H14B 0.9800 . ? 
C14 H14C 0.9800 . ? 
 
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 
C2 C1 C6 123.8(3) . . ? 
C2 C1 Br1 122.0(3) . . ? 
C6 C1 Br1 114.2(2) . . ? 
C1 C2 C3 119.3(3) . . ? 
C1 C2 C11 125.2(3) . . ? 
C3 C2 C11 115.3(3) . . ? 
O2 C3 C4 121.6(3) . . ? 
O2 C3 C2 119.3(3) . . ? 
C4 C3 C2 119.1(3) . . ? 
C5 C4 C7 120.0(3) . . ? 
C5 C4 C3 120.3(3) . . ? 
C7 C4 C3 119.8(3) . . ? 
C10 C5 C4 119.9(3) . . ? 
C10 C5 C6 119.2(3) . . ? 
C4 C5 C6 120.8(3) . . ? 
O1 C6 C5 121.7(3) . . ? 
O1 C6 C1 121.7(3) . . ? 
C5 C6 C1 116.6(3) . . ? 
C8 C7 C4 119.8(3) . . ? 
C8 C7 H7 120.1 . . ? 
C4 C7 H7 120.1 . . ? 
C7 C8 C9 120.3(3) . . ? 
C7 C8 H8 119.9 . . ? 
C9 C8 H8 119.9 . . ? 
C10 C9 C8 120.2(3) . . ? 
C10 C9 H9 119.9 . . ? 
C8 C9 H9 119.9 . . ? 
C9 C10 C5 119.8(3) . . ? 
C9 C10 H10 120.1 . . ? 
C5 C10 H10 120.1 . . ? 
C2 C11 C12 110.7(3) . . ? 
C2 C11 H11A 109.5 . . ? 
C12 C11 H11A 109.5 . . ? 
C2 C11 H11B 109.5 . . ? 
C12 C11 H11B 109.5 . . ? 
H11A C11 H11B 108.1 . . ? 
O3 C12 O4 124.9(3) . . ? 
O3 C12 C11 124.5(3) . . ? 
O4 C12 C11 110.6(3) . . ? 
O4 C13 C14 107.0(3) . . ? 
O4 C13 H13A 110.3 . . ? 
C14 C13 H13A 110.3 . . ? 
O4 C13 H13B 110.3 . . ? 
C14 C13 H13B 110.3 . . ? 
H13A C13 H13B 108.6 . . ? 
C13 C14 H14A 109.5 . . ? 
C13 C14 H14B 109.5 . . ? 
H14A C14 H14B 109.5 . . ? 
C13 C14 H14C 109.5 . . ? 
H14A C14 H14C 109.5 . . ? 
H14B C14 H14C 109.5 . . ? 
C12 O4 C13 115.5(3) . . ? 
 
_diffrn_measured_fraction_theta_max    0.994 
_diffrn_reflns_theta_full              27.48 
_diffrn_measured_fraction_theta_full   0.994 
_refine_diff_density_max    0.474 
_refine_diff_density_min   -0.557 
_refine_diff_density_rms    0.099 
