
# ol0155182.cif
 
data_cwd33t 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C13 H14 Br Cl O3' 
_chemical_formula_weight          333.60 
 
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' 
 'Cl'  'Cl'   0.1484   0.1585 
 '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            ? 
_symmetry_space_group_name_H-M    ? 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z' 
 
_cell_length_a                    9.0192(12) 
_cell_length_b                    4.9332(6) 
_cell_length_c                    15.1987(19) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  106.981(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      646.76(14) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     213(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        ? 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           ? 
_exptl_crystal_size_mid           ? 
_exptl_crystal_size_min           ? 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.713 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              336 
_exptl_absorpt_coefficient_mu     3.381 
_exptl_absorpt_correction_type    ? 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       213(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   ? 
_diffrn_measurement_method        ? 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             4196 
_diffrn_reflns_av_R_equivalents   0.0553 
_diffrn_reflns_av_sigmaI/netI     0.0556 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        -6 
_diffrn_reflns_limit_k_max        2 
_diffrn_reflns_limit_l_min        -18 
_diffrn_reflns_limit_l_max        19 
_diffrn_reflns_theta_min          1.40 
_diffrn_reflns_theta_max          27.85 
_reflns_number_total              2034 
_reflns_number_gt                 1448 
_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 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)+(0.0635P)²+0.0000P] where P=(Fo²+2Fc²)/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    -0.005(15) 
_refine_ls_number_reflns          2034 
_refine_ls_number_parameters      154 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0597 
_refine_ls_R_factor_gt            0.0393 
_refine_ls_wR_factor_ref          0.1046 
_refine_ls_wR_factor_gt           0.0952 
_refine_ls_goodness_of_fit_ref    0.931 
_refine_ls_restrained_S_all       0.931 
_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 -0.81213(7) -0.50450(12) -0.49311(3) 0.0883(3) Uani 1 1 d . . . 
Cl1 Cl -1.53948(14) -0.0052(4) -1.34291(7) 0.0657(3) Uani 1 1 d . . . 
O3 O -1.4725(3) 0.0374(6) -1.0321(2) 0.0385(7) Uani 1 1 d . . . 
H3A H -1.4899 -0.1132 -1.0128 0.058 Uiso 1 1 calc R . . 
C5 C -0.8376(5) 0.0223(13) -0.7060(3) 0.0533(12) Uani 1 1 d . . . 
H5A H -0.7751 0.1609 -0.7184 0.064 Uiso 1 1 calc R . . 
O2 O -1.1593(3) 0.0392(6) -0.91495(18) 0.0402(7) Uani 1 1 d . . . 
C9 C -1.3387(4) 0.0200(9) -1.0651(2) 0.0329(8) Uani 1 1 d . . . 
H9A H -1.3083 -0.1726 -1.0658 0.039 Uiso 1 1 calc R . . 
C8 C -1.2053(5) 0.1760(9) -1.0030(3) 0.0372(10) Uani 1 1 d . . . 
H8A H -1.1184 0.1816 -1.0295 0.045 Uiso 1 1 calc R . . 
H8B H -1.2370 0.3625 -0.9955 0.045 Uiso 1 1 calc R . . 
C4 C -0.9754(4) -0.0388(11) -0.7706(3) 0.0404(9) Uani 1 1 d . . . 
C10 C -1.3770(5) 0.1310(8) -1.1614(3) 0.0356(9) Uani 1 1 d . . . 
H10A H -1.2889 0.1362 -1.1879 0.043 Uiso 1 1 calc R . . 
C3 C -1.0666(5) -0.2448(10) -0.7504(3) 0.0462(11) Uani 1 1 d . . . 
H3B H -1.1615 -0.2894 -0.7935 0.055 Uiso 1 1 calc R . . 
C7 C -1.0187(5) 0.1080(9) -0.8575(3) 0.0440(11) Uani 1 1 d . . . 
C1 C -0.8812(6) -0.3141(11) -0.6052(3) 0.0540(13) Uani 1 1 d . . . 
C2 C -1.0196(6) -0.3834(11) -0.6684(3) 0.0585(13) Uani 1 1 d . . . 
H2A H -1.0810 -0.5233 -0.6557 0.070 Uiso 1 1 calc R . . 
C6 C -0.7888(6) -0.1140(11) -0.6236(4) 0.0600(14) Uani 1 1 d . . . 
H6A H -0.6935 -0.0708 -0.5806 0.072 Uiso 1 1 calc R . . 
O1 O -0.9394(4) 0.2770(9) -0.8803(2) 0.0685(11) Uani 1 1 d . . . 
C11 C -1.4958(5) 0.3527(8) -1.1946(3) 0.0450(11) Uani 1 1 d . . . 
H11A H -1.5490 0.4218 -1.1515 0.054 Uiso 1 1 calc R . . 
H11B H -1.4762 0.4879 -1.2372 0.054 Uiso 1 1 calc R . . 
C12 C -1.5298(5) 0.0724(9) -1.2285(3) 0.0440(10) Uani 1 1 d . . . 
H12A H -1.6037 -0.0276 -1.2035 0.053 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 0.1148(5) 0.0771(4) 0.0493(3) 0.0056(4) -0.0133(3) 0.0009(5) 
Cl1 0.0715(7) 0.0606(7) 0.0487(6) 0.0022(9) -0.0081(5) 0.0081(8) 
O3 0.0306(13) 0.0300(16) 0.0627(16) 0.0038(14) 0.0259(12) 0.0022(12) 
C5 0.037(2) 0.064(3) 0.059(3) -0.014(3) 0.013(2) -0.011(3) 
O2 0.0320(14) 0.043(2) 0.0449(14) 0.0022(14) 0.0101(12) -0.0079(14) 
C9 0.0271(18) 0.028(2) 0.0470(19) -0.002(2) 0.0162(16) 0.0015(19) 
C8 0.031(2) 0.037(2) 0.046(2) 0.0035(19) 0.014(2) -0.0036(18) 
C4 0.0301(19) 0.048(2) 0.046(2) -0.004(3) 0.0154(17) 0.000(2) 
C10 0.031(2) 0.030(2) 0.048(2) 0.0026(18) 0.0140(19) 0.0030(17) 
C3 0.037(2) 0.051(3) 0.046(3) -0.003(2) 0.005(2) -0.006(2) 
C7 0.036(2) 0.049(3) 0.049(3) -0.010(2) 0.016(2) -0.004(2) 
C1 0.059(3) 0.054(3) 0.042(3) 0.000(2) 0.004(2) 0.008(2) 
C2 0.057(3) 0.062(3) 0.052(3) 0.007(2) 0.007(3) -0.007(2) 
C6 0.050(3) 0.064(3) 0.053(3) -0.013(2) -0.005(2) 0.004(3) 
O1 0.053(2) 0.090(3) 0.060(2) 0.007(2) 0.0125(18) -0.036(2) 
C11 0.046(3) 0.031(2) 0.058(3) 0.012(2) 0.015(2) 0.008(2) 
C12 0.034(2) 0.041(2) 0.054(2) 0.002(2) 0.007(2) 0.0084(18) 
 
_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 C1 1.885(5) . ? 
Cl1 C12 1.757(5) . ? 
O3 C9 1.439(4) . ? 
C5 C4 1.373(6) . ? 
C5 C6 1.376(7) . ? 
O2 C7 1.356(5) . ? 
O2 C8 1.447(5) . ? 
C9 C10 1.506(6) . ? 
C9 C8 1.506(6) . ? 
C4 C3 1.397(6) . ? 
C4 C7 1.456(7) . ? 
C10 C12 1.484(6) . ? 
C10 C11 1.510(5) . ? 
C3 C2 1.375(7) . ? 
C7 O1 1.214(5) . ? 
C1 C6 1.372(7) . ? 
C1 C2 1.377(7) . ? 
C11 C12 1.476(6) . ? 
 
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 
C4 C5 C6 121.7(5) . . ? 
C7 O2 C8 116.2(3) . . ? 
O3 C9 C10 109.9(3) . . ? 
O3 C9 C8 110.4(3) . . ? 
C10 C9 C8 109.8(3) . . ? 
O2 C8 C9 107.6(3) . . ? 
C5 C4 C3 118.1(4) . . ? 
C5 C4 C7 119.1(4) . . ? 
C3 C4 C7 122.8(4) . . ? 
C12 C10 C9 120.0(4) . . ? 
C12 C10 C11 59.1(3) . . ? 
C9 C10 C11 121.8(4) . . ? 
C2 C3 C4 121.0(4) . . ? 
O1 C7 O2 120.4(4) . . ? 
O1 C7 C4 125.2(4) . . ? 
O2 C7 C4 114.4(4) . . ? 
C6 C1 C2 121.2(5) . . ? 
C6 C1 Br1 118.8(4) . . ? 
C2 C1 Br1 120.0(4) . . ? 
C3 C2 C1 119.0(5) . . ? 
C1 C6 C5 119.0(5) . . ? 
C12 C11 C10 59.6(3) . . ? 
C11 C12 C10 61.4(3) . . ? 
C11 C12 Cl1 119.6(3) . . ? 
C10 C12 Cl1 119.3(3) . . ? 
 
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 
C7 O2 C8 C9 164.4(3) . . . . ? 
O3 C9 C8 O2 66.4(4) . . . . ? 
C10 C9 C8 O2 -172.3(3) . . . . ? 
C6 C5 C4 C3 0.2(7) . . . . ? 
C6 C5 C4 C7 -178.4(4) . . . . ? 
O3 C9 C10 C12 -40.0(5) . . . . ? 
C8 C9 C10 C12 -161.6(3) . . . . ? 
O3 C9 C10 C11 30.2(5) . . . . ? 
C8 C9 C10 C11 -91.4(4) . . . . ? 
C5 C4 C3 C2 -0.3(7) . . . . ? 
C7 C4 C3 C2 178.3(4) . . . . ? 
C8 O2 C7 O1 0.6(6) . . . . ? 
C8 O2 C7 C4 -178.6(3) . . . . ? 
C5 C4 C7 O1 3.1(7) . . . . ? 
C3 C4 C7 O1 -175.4(4) . . . . ? 
C5 C4 C7 O2 -177.7(4) . . . . ? 
C3 C4 C7 O2 3.7(6) . . . . ? 
C4 C3 C2 C1 0.8(7) . . . . ? 
C6 C1 C2 C3 -1.3(8) . . . . ? 
Br1 C1 C2 C3 -179.0(4) . . . . ? 
C2 C1 C6 C5 1.3(8) . . . . ? 
Br1 C1 C6 C5 179.0(4) . . . . ? 
C4 C5 C6 C1 -0.7(7) . . . . ? 
C9 C10 C11 C12 -108.4(4) . . . . ? 
C10 C11 C12 Cl1 -109.4(4) . . . . ? 
C9 C10 C12 C11 111.3(4) . . . . ? 
C9 C10 C12 Cl1 -138.9(4) . . . . ? 
C11 C10 C12 Cl1 109.8(4) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.919 
_diffrn_reflns_theta_full              27.85 
_diffrn_measured_fraction_theta_full   0.919 
_refine_diff_density_max    0.507 
_refine_diff_density_min   -0.588 
_refine_diff_density_rms    0.074 

#===END

