 
data_ga_200602a_a 
  
_audit_creation_method            'SHELXL-2016/6' 
_shelx_SHELXL_version_number      '2016/6' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C15 H11 Br O2' 
_chemical_formula_weight          303.15 
  
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0137   0.0067 
 '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' 
 'Br'  'Br'  -0.9338   1.0006 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0389   0.0241 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       monoclinic 
_space_group_IT_number            14 
_space_group_name_H-M_alt         'P 21/n' 
_space_group_name_Hall            '-P 2yn' 
  
_shelx_space_group_comment 
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-x+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x-1/2, -y-1/2, z-1/2' 
  
_cell_length_a                    9.5102(5) 
_cell_length_b                    8.4541(5) 
_cell_length_c                    16.7220(9) 
_cell_angle_alpha                 90 
_cell_angle_beta                  104.133(2) 
_cell_angle_gamma                 90 
_cell_volume                      1303.76(13) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     173(2) 
_cell_measurement_reflns_used     1214 
_cell_measurement_theta_min       5.13 
_cell_measurement_theta_max       32.24 
  
_exptl_crystal_description        block 
_exptl_crystal_colour             colourless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.544 
_exptl_crystal_F_000              608 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.100 
_exptl_crystal_size_mid           0.100 
_exptl_crystal_size_min           0.100 
_exptl_absorpt_coefficient_mu     2.789 
_shelx_estimated_absorpt_T_min    0.768 
_shelx_estimated_absorpt_T_max    0.768 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.660 
_exptl_absorpt_correction_T_max   0.751 
_exptl_absorpt_process_details    sadabs 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       173(2) 
_diffrn_radiation_wavelength      1.34138 
_diffrn_radiation_type            GaK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'Bruker APEX-II CCD' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             11571 
_diffrn_reflns_av_unetI/netI      0.0309 
_diffrn_reflns_av_R_equivalents   0.0394 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -10 
_diffrn_reflns_limit_k_max        10 
_diffrn_reflns_limit_l_min        -20 
_diffrn_reflns_limit_l_max        20 
_diffrn_reflns_theta_min          4.265 
_diffrn_reflns_theta_max          56.463 
_diffrn_reflns_theta_full         53.594 
_diffrn_measured_fraction_theta_max   0.995 
_diffrn_measured_fraction_theta_full  0.995 
_diffrn_reflns_Laue_measured_fraction_max    0.995 
_diffrn_reflns_Laue_measured_fraction_full   0.995 
_diffrn_reflns_point_group_measured_fraction_max   0.995 
_diffrn_reflns_point_group_measured_fraction_full  0.995 
_reflns_number_total              2617 
_reflns_number_gt                 2429 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.000 
_reflns_Friedel_fraction_max      . 
_reflns_Friedel_fraction_full     . 
  
_reflns_special_details 
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
; 
  
_computing_data_collection        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)' 
_computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
_refine_special_details           ? 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0394P)²+1.1492P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_number_reflns          2617 
_refine_ls_number_parameters      164 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0349 
_refine_ls_R_factor_gt            0.0322 
_refine_ls_wR_factor_ref          0.0861 
_refine_ls_wR_factor_gt           0.0835 
_refine_ls_goodness_of_fit_ref    1.044 
_refine_ls_restrained_S_all       1.044 
_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_site_symmetry_order 
 _atom_site_calc_flag 
 _atom_site_refinement_flags_posn 
 _atom_site_refinement_flags_adp 
 _atom_site_refinement_flags_occupancy 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
Br1 Br 0.71969(3) 0.57131(3) 0.06304(2) 0.04614(12) Uani 1 1 d . . . . . 
O1 O 0.46103(17) 0.82192(17) 0.45998(9) 0.0328(3) Uani 1 1 d . . . . . 
O2 O 0.31097(18) 0.7907(2) 0.33537(11) 0.0472(5) Uani 1 1 d . . . . . 
C1 C 0.4133(2) 0.7437(3) 0.38665(13) 0.0298(4) Uani 1 1 d . . . . . 
C2 C 0.5075(2) 0.5986(2) 0.38371(12) 0.0224(4) Uani 1 1 d . . . . . 
H2 H 0.448357 0.501908 0.386518 0.027 Uiso 1 1 calc R U . . . 
C3 C 0.6192(2) 0.6144(2) 0.46402(11) 0.0212(4) Uani 1 1 d . . . . . 
C4 C 0.7395(2) 0.5248(2) 0.50031(13) 0.0260(4) Uani 1 1 d . . . . . 
H4 H 0.765347 0.435675 0.472351 0.031 Uiso 1 1 calc R U . . . 
C5 C 0.8229(2) 0.5665(3) 0.57849(14) 0.0320(5) Uani 1 1 d . . . . . 
C6 C 0.7816(3) 0.6972(3) 0.61820(13) 0.0359(5) Uani 1 1 d . . . . . 
H6 H 0.837364 0.724092 0.671720 0.043 Uiso 1 1 calc R U . . . 
C7 C 0.6628(3) 0.7887(3) 0.58276(14) 0.0359(5) Uani 1 1 d . . . . . 
H7 H 0.636680 0.878357 0.610213 0.043 Uiso 1 1 calc R U . . . 
C8 C 0.5837(2) 0.7440(2) 0.50541(12) 0.0261(4) Uani 1 1 d . . . . . 
C9 C 0.5598(2) 0.5910(2) 0.30550(12) 0.0204(4) Uani 1 1 d . . . . . 
C10 C 0.4886(2) 0.4962(2) 0.24014(12) 0.0249(4) Uani 1 1 d . . . . . 
H10 H 0.408109 0.434065 0.245452 0.030 Uiso 1 1 calc R U . . . 
C11 C 0.5336(2) 0.4912(2) 0.16745(12) 0.0288(4) Uani 1 1 d . . . . . 
H11 H 0.484323 0.426453 0.122933 0.035 Uiso 1 1 calc R U . . . 
C12 C 0.6509(2) 0.5814(2) 0.16049(13) 0.0277(4) Uani 1 1 d . . . . . 
C13 C 0.7228(2) 0.6770(3) 0.22403(14) 0.0336(5) Uani 1 1 d . . . . . 
H13 H 0.802905 0.739313 0.218252 0.040 Uiso 1 1 calc R U . . . 
C14 C 0.6770(2) 0.6813(3) 0.29644(13) 0.0295(4) Uani 1 1 d . . . . . 
H14 H 0.726268 0.746903 0.340544 0.035 Uiso 1 1 calc R U . . . 
C15 C 0.9540(3) 0.4691(4) 0.61949(18) 0.0491(7) Uani 1 1 d . . . . . 
H15A H 1.034957 0.539730 0.643585 0.074 Uiso 1 1 calc R U . . . 
H15B H 0.981083 0.400573 0.578428 0.074 Uiso 1 1 calc R U . . . 
H15C H 0.930825 0.403968 0.663033 0.074 Uiso 1 1 calc R U . . . 
  
  
_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 C12 1.900(2) . ? 
O1 C1 1.369(3) . ? 
O1 C8 1.393(3) . ? 
O2 C1 1.197(3) . ? 
C1 C2 1.527(3) . ? 
C2 C3 1.501(3) . ? 
C2 C9 1.510(3) . ? 
C2 H2 1.0000 . ? 
C3 C8 1.381(3) . ? 
C3 C4 1.383(3) . ? 
C4 C5 1.399(3) . ? 
C4 H4 0.9500 . ? 
C5 C6 1.394(3) . ? 
C5 C15 1.511(3) . ? 
C6 C7 1.378(4) . ? 
C6 H6 0.9500 . ? 
C7 C8 1.381(3) . ? 
C7 H7 0.9500 . ? 
C9 C14 1.389(3) . ? 
C9 C10 1.391(3) . ? 
C10 C11 1.384(3) . ? 
C10 H10 0.9500 . ? 
C11 C12 1.380(3) . ? 
C11 H11 0.9500 . ? 
C12 C13 1.377(3) . ? 
C13 C14 1.384(3) . ? 
C13 H13 0.9500 . ? 
C14 H14 0.9500 . ? 
C15 H15A 0.9800 . ? 
C15 H15B 0.9800 . ? 
C15 H15C 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 
C1 O1 C8 108.09(15) . . ? 
O2 C1 O1 121.0(2) . . ? 
O2 C1 C2 128.6(2) . . ? 
O1 C1 C2 110.35(16) . . ? 
C3 C2 C9 117.90(16) . . ? 
C3 C2 C1 101.09(16) . . ? 
C9 C2 C1 112.47(16) . . ? 
C3 C2 H2 108.3 . . ? 
C9 C2 H2 108.3 . . ? 
C1 C2 H2 108.3 . . ? 
C8 C3 C4 119.46(18) . . ? 
C8 C3 C2 108.25(17) . . ? 
C4 C3 C2 132.27(18) . . ? 
C3 C4 C5 119.4(2) . . ? 
C3 C4 H4 120.3 . . ? 
C5 C4 H4 120.3 . . ? 
C6 C5 C4 118.9(2) . . ? 
C6 C5 C15 120.8(2) . . ? 
C4 C5 C15 120.2(2) . . ? 
C7 C6 C5 122.5(2) . . ? 
C7 C6 H6 118.8 . . ? 
C5 C6 H6 118.8 . . ? 
C6 C7 C8 116.8(2) . . ? 
C6 C7 H7 121.6 . . ? 
C8 C7 H7 121.6 . . ? 
C3 C8 C7 122.89(19) . . ? 
C3 C8 O1 112.11(17) . . ? 
C7 C8 O1 124.99(19) . . ? 
C14 C9 C10 118.75(18) . . ? 
C14 C9 C2 120.91(17) . . ? 
C10 C9 C2 120.32(17) . . ? 
C11 C10 C9 120.78(18) . . ? 
C11 C10 H10 119.6 . . ? 
C9 C10 H10 119.6 . . ? 
C12 C11 C10 119.13(18) . . ? 
C12 C11 H11 120.4 . . ? 
C10 C11 H11 120.4 . . ? 
C13 C12 C11 121.27(19) . . ? 
C13 C12 Br1 118.57(16) . . ? 
C11 C12 Br1 120.14(16) . . ? 
C12 C13 C14 119.17(19) . . ? 
C12 C13 H13 120.4 . . ? 
C14 C13 H13 120.4 . . ? 
C13 C14 C9 120.90(19) . . ? 
C13 C14 H14 119.5 . . ? 
C9 C14 H14 119.5 . . ? 
C5 C15 H15A 109.5 . . ? 
C5 C15 H15B 109.5 . . ? 
H15A C15 H15B 109.5 . . ? 
C5 C15 H15C 109.5 . . ? 
H15A C15 H15C 109.5 . . ? 
H15B C15 H15C 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 
C8 O1 C1 O2 -177.8(2) . . . . ? 
C8 O1 C1 C2 2.3(2) . . . . ? 
O2 C1 C2 C3 176.8(2) . . . . ? 
O1 C1 C2 C3 -3.2(2) . . . . ? 
O2 C1 C2 C9 50.1(3) . . . . ? 
O1 C1 C2 C9 -129.91(17) . . . . ? 
C9 C2 C3 C8 126.04(18) . . . . ? 
C1 C2 C3 C8 3.0(2) . . . . ? 
C9 C2 C3 C4 -55.5(3) . . . . ? 
C1 C2 C3 C4 -178.5(2) . . . . ? 
C8 C3 C4 C5 0.3(3) . . . . ? 
C2 C3 C4 C5 -178.0(2) . . . . ? 
C3 C4 C5 C6 0.5(3) . . . . ? 
C3 C4 C5 C15 179.4(2) . . . . ? 
C4 C5 C6 C7 -1.1(3) . . . . ? 
C15 C5 C6 C7 180.0(2) . . . . ? 
C5 C6 C7 C8 0.9(3) . . . . ? 
C4 C3 C8 C7 -0.6(3) . . . . ? 
C2 C3 C8 C7 178.14(19) . . . . ? 
C4 C3 C8 O1 179.28(17) . . . . ? 
C2 C3 C8 O1 -2.0(2) . . . . ? 
C6 C7 C8 C3 0.0(3) . . . . ? 
C6 C7 C8 O1 -179.85(19) . . . . ? 
C1 O1 C8 C3 -0.2(2) . . . . ? 
C1 O1 C8 C7 179.7(2) . . . . ? 
C3 C2 C9 C14 -37.3(3) . . . . ? 
C1 C2 C9 C14 79.7(2) . . . . ? 
C3 C2 C9 C10 144.44(18) . . . . ? 
C1 C2 C9 C10 -98.5(2) . . . . ? 
C14 C9 C10 C11 0.2(3) . . . . ? 
C2 C9 C10 C11 178.48(17) . . . . ? 
C9 C10 C11 C12 0.2(3) . . . . ? 
C10 C11 C12 C13 -0.6(3) . . . . ? 
C10 C11 C12 Br1 177.72(15) . . . . ? 
C11 C12 C13 C14 0.6(3) . . . . ? 
Br1 C12 C13 C14 -177.79(17) . . . . ? 
C12 C13 C14 C9 -0.1(3) . . . . ? 
C10 C9 C14 C13 -0.3(3) . . . . ? 
C2 C9 C14 C13 -178.51(19) . . . . ? 
  
_refine_diff_density_max    0.854 
_refine_diff_density_min   -0.669 
_refine_diff_density_rms    0.068 
  
  
  
