# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_Form-I
_database_code_depnum_ccdc_archive 'CCDC 1833685'
_audit_update_record             
;
2018-03-30 deposited with the CCDC.
2018-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H8 Br2 O2'
_chemical_formula_weight         356.01

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'

_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                   15.484(13)
_cell_length_b                   4.021(3)
_cell_length_c                   19.824(15)
_cell_angle_alpha                90
_cell_angle_beta                 90.285(12)
_cell_angle_gamma                90
_cell_volume                     1234.2(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2510
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      33.8

_exptl_crystal_description       Block
_exptl_crystal_colour            Paleyellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.916
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    6.553
_shelx_estimated_absorpt_T_min   0.461
_shelx_estimated_absorpt_T_max   0.507
_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.547

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            9716
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_av_R_equivalents  0.1046
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.673
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             2163
_reflns_number_gt                1830
_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       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXL-14 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-14 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0709P)²+1.5530P] 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         2163
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1399
_refine_ls_wR_factor_gt          0.1322
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.002

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
C1 C 0.2919(3) -0.0509(14) 0.0857(3) 0.0445(12) Uani 1 1 d . . . . .
C2 C 0.2260(4) -0.2147(15) 0.0535(3) 0.0519(14) Uani 1 1 d . . . . .
H2 H 0.1725 -0.2508 0.0755 0.062 Uiso 1 1 calc R U . . .
C3 C 0.2385(3) -0.3261(15) -0.0114(3) 0.0499(13) Uani 1 1 d . . . . .
H3 H 0.1930 -0.4362 -0.0346 0.060 Uiso 1 1 calc R U . . .
C4 C 0.3179(3) -0.2784(14) -0.0435(3) 0.0417(12) Uani 1 1 d . . . . .
C5 C 0.3817(3) -0.1068(15) -0.0095(3) 0.0473(13) Uani 1 1 d . . . . .
H5 H 0.4348 -0.0623 -0.0314 0.057 Uiso 1 1 calc R U . . .
C6 C 0.3699(4) 0.0013(16) 0.0557(3) 0.0510(13) Uani 1 1 d . . . . .
H6 H 0.4153 0.1104 0.0793 0.061 Uiso 1 1 calc R U . . .
C7 C 0.3284(3) -0.4144(15) -0.1115(3) 0.0473(13) Uani 1 1 d . . . . .
C8 C 0.4250(3) -0.4430(14) -0.2040(3) 0.0436(12) Uani 1 1 d . . . . .
C9 C 0.3731(3) -0.3671(15) -0.2580(3) 0.0451(12) Uani 1 1 d . . . . .
H9 H 0.3206 -0.2492 -0.2514 0.054 Uiso 1 1 calc R U . . .
C10 C 0.3972(3) -0.4623(14) -0.3214(3) 0.0450(12) Uani 1 1 d . . . . .
H10 H 0.3615 -0.4120 -0.3591 0.054 Uiso 1 1 calc R U . . .
C11 C 0.4731(3) -0.6304(13) -0.3302(2) 0.0404(11) Uani 1 1 d . . . . .
C12 C 0.5263(4) -0.7062(15) -0.2761(3) 0.0490(13) Uani 1 1 d . . . . .
H12 H 0.5794 -0.8195 -0.2831 0.059 Uiso 1 1 calc R U . . .
C13 C 0.5017(3) -0.6164(15) -0.2126(3) 0.0469(13) Uani 1 1 d . . . . .
H13 H 0.5366 -0.6720 -0.1747 0.056 Uiso 1 1 calc R U . . .
O1 O 0.4062(2) -0.3344(11) -0.13859(18) 0.0502(9) Uani 1 1 d . . . . .
O2 O 0.2767(3) -0.5879(14) -0.1401(2) 0.0711(14) Uani 1 1 d . . . . .
Br1 Br 0.27518(5) 0.10712(18) 0.17518(3) 0.0638(3) Uani 1 1 d . . . . .
Br2 Br 0.50586(4) -0.76411(16) -0.41850(3) 0.0590(3) Uani 1 1 d . . . . .


_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 C6 1.366(7) . ?
C1 C2 1.370(8) . ?
C1 Br1 1.903(5) . ?
C2 C3 1.377(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.399(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(8) . ?
C4 C7 1.464(8) . ?
C5 C6 1.375(8) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O2 1.202(7) . ?
C7 O1 1.360(7) . ?
C8 C9 1.369(7) . ?
C8 C13 1.388(8) . ?
C8 O1 1.401(6) . ?
C9 C10 1.369(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.367(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(8) . ?
C11 Br2 1.903(5) . ?
C12 C13 1.367(8) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?

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
C6 C1 C2 121.9(5) . . ?
C6 C1 Br1 118.7(4) . . ?
C2 C1 Br1 119.4(4) . . ?
C3 C2 C1 118.9(5) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 120.5(5) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 118.4(5) . . ?
C5 C4 C7 123.7(5) . . ?
C3 C4 C7 117.9(5) . . ?
C6 C5 C4 121.3(5) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 118.8(5) . . ?
C5 C6 H6 120.6 . . ?
C1 C6 H6 120.6 . . ?
O2 C7 O1 122.6(5) . . ?
O2 C7 C4 125.1(5) . . ?
O1 C7 C4 112.2(4) . . ?
C9 C8 C13 121.0(5) . . ?
C9 C8 O1 122.0(5) . . ?
C13 C8 O1 116.8(5) . . ?
C10 C9 C8 119.6(5) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C9 119.6(5) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 121.3(5) . . ?
C10 C11 Br2 119.3(4) . . ?
C12 C11 Br2 119.4(4) . . ?
C13 C12 C11 119.2(5) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C8 119.2(5) . . ?
C12 C13 H13 120.4 . . ?
C8 C13 H13 120.4 . . ?
C7 O1 C8 118.8(4) . . ?

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
C6 C1 C2 C3 -0.8(9) . . . . ?
Br1 C1 C2 C3 179.6(4) . . . . ?
C1 C2 C3 C4 1.2(9) . . . . ?
C2 C3 C4 C5 -2.4(9) . . . . ?
C2 C3 C4 C7 177.6(5) . . . . ?
C3 C4 C5 C6 3.3(9) . . . . ?
C7 C4 C5 C6 -176.7(6) . . . . ?
C4 C5 C6 C1 -2.9(9) . . . . ?
C2 C1 C6 C5 1.6(9) . . . . ?
Br1 C1 C6 C5 -178.7(5) . . . . ?
C5 C4 C7 O2 173.5(6) . . . . ?
C3 C4 C7 O2 -6.4(9) . . . . ?
C5 C4 C7 O1 -3.7(8) . . . . ?
C3 C4 C7 O1 176.3(5) . . . . ?
C13 C8 C9 C10 -0.3(9) . . . . ?
O1 C8 C9 C10 176.0(5) . . . . ?
C8 C9 C10 C11 -0.3(9) . . . . ?
C9 C10 C11 C12 -0.1(9) . . . . ?
C9 C10 C11 Br2 179.6(4) . . . . ?
C10 C11 C12 C13 1.2(9) . . . . ?
Br2 C11 C12 C13 -178.5(4) . . . . ?
C11 C12 C13 C8 -1.8(9) . . . . ?
C9 C8 C13 C12 1.4(9) . . . . ?
O1 C8 C13 C12 -175.1(5) . . . . ?
O2 C7 O1 C8 3.6(9) . . . . ?
C4 C7 O1 C8 -179.0(5) . . . . ?
C9 C8 O1 C7 56.4(7) . . . . ?
C13 C8 O1 C7 -127.1(5) . . . . ?

_refine_diff_density_max         1.200
_refine_diff_density_min         -0.711
_refine_diff_density_rms         0.108

_shelxl_version_number           2014-3

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_Form-II
_database_code_depnum_ccdc_archive 'CCDC 1833686'
_audit_update_record             
;
2018-03-30 deposited with the CCDC.
2018-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H8 Br2 O2'
_chemical_formula_weight         356.01

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           Orthorhombic
_symmetry_space_group_name_H-M   Pna21

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   7.859(5)
_cell_length_b                   6.118(4)
_cell_length_c                   24.872(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1195.9(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4402
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      33.7

_exptl_crystal_description       Block
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.977
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    6.763
_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_correction_T_min  0.4975
_exptl_absorpt_correction_T_max  0.5512

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10066
_diffrn_reflns_av_R_equivalents  0.1764
_diffrn_reflns_av_sigmaI/netI    0.1085
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2333
_reflns_number_gt                2225
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(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)+(0.1333P)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   0.03(3)
_refine_ls_number_reflns         2333
_refine_ls_number_parameters     154
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0756
_refine_ls_wR_factor_ref         0.1966
_refine_ls_wR_factor_gt          0.1834
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.002
_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
C001 C 0.1245(11) 0.8142(10) 0.1506(4) 0.0232(19) Uani 1 1 d . . .
H001 H 0.0779 0.6711 0.1489 0.028 Uiso 1 1 calc R . .
C002 C 0.0840(12) 1.3080(11) -0.0671(4) 0.025(2) Uani 1 1 d . . .
H002 H 0.1424 1.1728 -0.0707 0.030 Uiso 1 1 calc R . .
C003 C 0.1674(11) 1.3171(10) 0.0647(4) 0.0214(17) Uani 1 1 d . . .
C005 C 0.1845(11) 1.1610(12) 0.1103(4) 0.0196(16) Uani 1 1 d . . .
C006 C -0.0842(12) 1.7043(13) -0.0557(4) 0.0229(18) Uani 1 1 d . . .
H006 H -0.1416 1.8402 -0.0521 0.028 Uiso 1 1 calc R . .
C007 C -0.0291(11) 1.6362(15) -0.1050(4) 0.0260(17) Uani 1 1 d . . .
C008 C 0.2081(11) 0.8849(15) 0.1975(3) 0.0239(16) Uani 1 1 d . . .
C010 C 0.0518(10) 1.4356(13) -0.1119(3) 0.0259(16) Uani 1 1 d . . .
H010 H 0.0842 1.3873 -0.1467 0.031 Uiso 1 1 calc R . .
C011 C 0.2814(11) 1.0910(14) 0.2005(4) 0.0276(17) Uani 1 1 d . . .
H011 H 0.3399 1.1375 0.2319 0.033 Uiso 1 1 calc R . .
C012 C 0.2667(11) 1.2258(15) 0.1564(4) 0.0259(17) Uani 1 1 d . . .
H012 H 0.3149 1.3681 0.1579 0.031 Uiso 1 1 calc R . .
C013 C -0.0562(10) 1.5745(14) -0.0111(4) 0.0277(18) Uani 1 1 d . . .
H013 H -0.0956 1.6179 0.0234 0.033 Uiso 1 1 calc R . .
C014 C 0.1104(9) 0.9509(12) 0.1077(3) 0.0212(15) Uani 1 1 d . . .
H014 H 0.0512 0.9055 0.0763 0.025 Uiso 1 1 calc R . .
C015 C 0.0314(10) 1.3779(14) -0.0180(4) 0.0238(16) Uani 1 1 d . . .
O1 O 0.0613(8) 1.2406(11) 0.0260(2) 0.0272(13) Uani 1 1 d . . .
O2 O 0.2336(7) 1.4948(10) 0.0636(3) 0.0303(14) Uani 1 1 d . . .
Br1 Br 0.22357(13) 0.68925(12) 0.25648(3) 0.0303(3) Uani 1 1 d . . .
Br2 Br -0.05574(13) 1.82289(12) -0.16593(3) 0.0325(3) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C001 C014 1.360(13) . ?
C001 C008 1.407(13) . ?
C001 H001 0.9500 . ?
C002 C015 1.359(14) . ?
C002 C010 1.384(12) . ?
C002 H002 0.9500 . ?
C003 O2 1.205(10) . ?
C003 O1 1.359(12) . ?
C003 C005 1.488(12) . ?
C005 C012 1.376(13) . ?
C005 C014 1.412(11) . ?
C006 C007 1.365(13) . ?
C006 C013 1.383(13) . ?
C006 H006 0.9500 . ?
C007 C010 1.392(13) . ?
C007 Br2 1.910(9) . ?
C008 C011 1.388(12) . ?
C008 Br1 1.897(9) . ?
C010 H010 0.9500 . ?
C011 C012 1.376(14) . ?
C011 H011 0.9500 . ?
C012 H012 0.9500 . ?
C013 C015 1.396(12) . ?
C013 H013 0.9500 . ?
C014 H014 0.9500 . ?
C015 O1 1.398(11) . ?

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
C014 C001 C008 120.0(7) . . ?
C014 C001 H001 120.0 . . ?
C008 C001 H001 120.0 . . ?
C015 C002 C010 119.4(7) . . ?
C015 C002 H002 120.3 . . ?
C010 C002 H002 120.3 . . ?
O2 C003 O1 123.9(8) . . ?
O2 C003 C005 124.0(8) . . ?
O1 C003 C005 112.0(6) . . ?
C012 C005 C014 119.6(8) . . ?
C012 C005 C003 119.5(7) . . ?
C014 C005 C003 120.9(7) . . ?
C007 C006 C013 119.7(8) . . ?
C007 C006 H006 120.2 . . ?
C013 C006 H006 120.2 . . ?
C006 C007 C010 121.6(8) . . ?
C006 C007 Br2 119.7(7) . . ?
C010 C007 Br2 118.7(7) . . ?
C011 C008 C001 121.1(8) . . ?
C011 C008 Br1 120.4(7) . . ?
C001 C008 Br1 118.5(7) . . ?
C002 C010 C007 118.8(8) . . ?
C002 C010 H010 120.6 . . ?
C007 C010 H010 120.6 . . ?
C012 C011 C008 117.9(8) . . ?
C012 C011 H011 121.0 . . ?
C008 C011 H011 121.0 . . ?
C011 C012 C005 122.0(8) . . ?
C011 C012 H012 119.0 . . ?
C005 C012 H012 119.0 . . ?
C006 C013 C015 118.3(8) . . ?
C006 C013 H013 120.8 . . ?
C015 C013 H013 120.8 . . ?
C001 C014 C005 119.4(7) . . ?
C001 C014 H014 120.3 . . ?
C005 C014 H014 120.3 . . ?
C002 C015 C013 122.1(8) . . ?
C002 C015 O1 117.5(8) . . ?
C013 C015 O1 120.3(8) . . ?
C003 O1 C015 116.8(7) . . ?

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
O2 C003 C005 C012 6.3(13) . . . . ?
O1 C003 C005 C012 -170.5(8) . . . . ?
O2 C003 C005 C014 -176.8(8) . . . . ?
O1 C003 C005 C014 6.5(11) . . . . ?
C013 C006 C007 C010 1.6(13) . . . . ?
C013 C006 C007 Br2 -176.3(6) . . . . ?
C014 C001 C008 C011 -1.9(13) . . . . ?
C014 C001 C008 Br1 179.7(6) . . . . ?
C015 C002 C010 C007 2.1(13) . . . . ?
C006 C007 C010 C002 -3.2(13) . . . . ?
Br2 C007 C010 C002 174.7(6) . . . . ?
C001 C008 C011 C012 1.3(12) . . . . ?
Br1 C008 C011 C012 179.8(7) . . . . ?
C008 C011 C012 C005 -0.8(13) . . . . ?
C014 C005 C012 C011 0.8(12) . . . . ?
C003 C005 C012 C011 177.8(8) . . . . ?
C007 C006 C013 C015 1.2(12) . . . . ?
C008 C001 C014 C005 1.8(12) . . . . ?
C012 C005 C014 C001 -1.3(11) . . . . ?
C003 C005 C014 C001 -178.3(7) . . . . ?
C010 C002 C015 C013 0.6(13) . . . . ?
C010 C002 C015 O1 177.8(7) . . . . ?
C006 C013 C015 C002 -2.3(11) . . . . ?
C006 C013 C015 O1 -179.4(8) . . . . ?
O2 C003 O1 C015 1.1(13) . . . . ?
C005 C003 O1 C015 177.9(7) . . . . ?
C002 C015 O1 C003 116.4(9) . . . . ?
C013 C015 O1 C003 -66.4(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.978
_refine_diff_density_min         -1.416
_refine_diff_density_rms         0.242
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_Form-III
_database_code_depnum_ccdc_archive 'CCDC 1833687'
_audit_update_record             
;
2018-03-30 deposited with the CCDC.
2018-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H8 Br2 O2'
_chemical_formula_weight         356.01

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   3.8549(9)
_cell_length_b                   11.732(2)
_cell_length_c                   27.480(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1242.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3397
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      33.6

_exptl_crystal_description       Block
_exptl_crystal_colour            Paleyellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.902
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    6.506
_shelx_estimated_absorpt_T_min   0.283
_shelx_estimated_absorpt_T_max   0.309
_exptl_absorpt_correction_type   multi-scan
# Example: '(North et al., 1968)'
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.593

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device       
;
XtaLABmini: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  
;
Rigaku Mercury375R (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_reflns_number            10537
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_av_R_equivalents  0.0984
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.283
_diffrn_reflns_theta_max         24.977
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             2186
_reflns_number_gt                2039
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.633
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    0.971

_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       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 rc14 (Rigaku, 2009)
;
_computing_structure_solution    'SHELXL-14 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-14 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1081P)²+3.2101P] 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_abs_structure_details 
;
 Flack x determined using 726 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.067(17)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2186
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1666
_refine_ls_wR_factor_gt          0.1616
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_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_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
C2 C 0.547(3) 1.1989(8) 0.1466(4) 0.037(2) Uani 1 1 d . . . . .
H003 H 0.5110 1.2742 0.1349 0.044 Uiso 1 1 calc R U . . .
C4 C 0.508(3) 0.9952(8) 0.1367(3) 0.031(2) Uani 1 1 d . . . . .
C3 C 0.449(3) 1.1044(8) 0.1187(3) 0.036(2) Uani 1 1 d . . . . .
H005 H 0.3437 1.1147 0.0878 0.043 Uiso 1 1 calc R U . . .
C5 C 0.653(3) 0.9795(9) 0.1816(4) 0.036(2) Uani 1 1 d . . . . .
H006 H 0.6863 0.9046 0.1939 0.043 Uiso 1 1 calc R U . . .
C13 C 0.457(3) 0.6728(8) 0.0550(3) 0.032(2) Uani 1 1 d . . . . .
H007 H 0.5766 0.7272 0.0356 0.038 Uiso 1 1 calc R U . . .
C12 C 0.355(3) 0.5692(8) 0.0356(4) 0.034(2) Uani 1 1 d . . . . .
H008 H 0.3990 0.5526 0.0023 0.040 Uiso 1 1 calc R U . . .
C1 C 0.695(3) 1.1799(9) 0.1912(3) 0.032(2) Uani 1 1 d . . . . .
C9 C 0.220(3) 0.6174(8) 0.1324(3) 0.031(2) Uani 1 1 d . . . . .
H011 H 0.1777 0.6343 0.1657 0.038 Uiso 1 1 calc R U . . .
C10 C 0.120(3) 0.5129(9) 0.1124(4) 0.038(2) Uani 1 1 d . . . . .
H012 H 0.0040 0.4579 0.1319 0.046 Uiso 1 1 calc R U . . .
C8 C 0.381(2) 0.6948(8) 0.1026(3) 0.029(2) Uani 1 1 d . . . . .
C11 C 0.190(3) 0.4902(8) 0.0644(3) 0.028(2) Uani 1 1 d . . . . .
C7 C 0.385(3) 0.8959(8) 0.1063(4) 0.034(2) Uani 1 1 d . . . . .
C6 C 0.752(3) 1.0730(9) 0.2092(3) 0.035(2) Uani 1 1 d . . . . .
H016 H 0.8574 1.0629 0.2401 0.042 Uiso 1 1 calc R U . . .
O1 O 0.488(2) 0.7975(5) 0.1253(2) 0.0371(16) Uani 1 1 d . . . . .
O2 O 0.205(2) 0.9056(6) 0.0711(3) 0.047(2) Uani 1 1 d . . . . .
Br1 Br 0.0439(3) 0.34939(8) 0.03679(4) 0.0392(4) Uani 1 1 d . . . . .
Br2 Br 0.8094(12) 1.3049(5) 0.22632(17) 0.0787(11) Uani 0.4427 1 d . . P . .
Br3 Br 0.950(5) 1.2598(11) 0.2586(5) 0.189(6) Uani 0.2984 1 d . . P . .
Br4 Br 0.723(5) 1.3724(11) 0.2066(4) 0.144(5) Uani 0.2584 1 d . . P . .


_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
C2 C1 1.370(14) . ?
C2 C3 1.399(14) . ?
C2 H003 0.9500 . ?
C4 C5 1.367(14) . ?
C4 C3 1.392(14) . ?
C4 C7 1.512(14) . ?
C3 H005 0.9500 . ?
C5 C6 1.387(14) . ?
C5 H006 0.9500 . ?
C13 C8 1.366(14) . ?
C13 C12 1.384(14) . ?
C13 H007 0.9500 . ?
C12 C11 1.377(14) . ?
C12 H008 0.9500 . ?
C1 C6 1.366(15) . ?
C1 Br2 1.811(10) . ?
C1 Br3 2.296(15) . ?
C1 Br4 2.301(16) . ?
C9 C8 1.372(14) . ?
C9 C10 1.398(14) . ?
C9 H011 0.9500 . ?
C10 C11 1.371(14) . ?
C10 H012 0.9500 . ?
C8 O1 1.418(11) . ?
C11 Br1 1.903(9) . ?
C7 O2 1.195(12) . ?
C7 O1 1.328(12) . ?
C6 H016 0.9500 . ?
Br2 Br4 1.016(13) . ?
Br2 Br3 1.165(15) . ?
Br3 Br4 2.13(2) . ?

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 C2 C3 118.2(9) . . ?
C1 C2 H003 120.9 . . ?
C3 C2 H003 120.9 . . ?
C5 C4 C3 120.8(9) . . ?
C5 C4 C7 121.6(9) . . ?
C3 C4 C7 117.5(8) . . ?
C4 C3 C2 119.4(9) . . ?
C4 C3 H005 120.3 . . ?
C2 C3 H005 120.3 . . ?
C4 C5 C6 119.9(9) . . ?
C4 C5 H006 120.1 . . ?
C6 C5 H006 120.1 . . ?
C8 C13 C12 118.3(9) . . ?
C8 C13 H007 120.9 . . ?
C12 C13 H007 120.9 . . ?
C13 C12 C11 120.1(9) . . ?
C13 C12 H008 120.0 . . ?
C11 C12 H008 120.0 . . ?
C2 C1 C6 122.7(9) . . ?
C2 C1 Br2 116.5(8) . . ?
C6 C1 Br2 120.7(8) . . ?
C2 C1 Br3 146.4(8) . . ?
C6 C1 Br3 90.8(7) . . ?
Br2 C1 Br3 30.1(4) . . ?
C2 C1 Br4 91.4(7) . . ?
C6 C1 Br4 145.8(8) . . ?
Br2 C1 Br4 25.2(3) . . ?
Br3 C1 Br4 55.3(5) . . ?
C8 C9 C10 118.1(9) . . ?
C8 C9 H011 121.0 . . ?
C10 C9 H011 121.0 . . ?
C11 C10 C9 119.6(10) . . ?
C11 C10 H012 120.2 . . ?
C9 C10 H012 120.2 . . ?
C13 C8 C9 123.0(9) . . ?
C13 C8 O1 121.3(9) . . ?
C9 C8 O1 115.6(8) . . ?
C10 C11 C12 121.0(9) . . ?
C10 C11 Br1 119.6(8) . . ?
C12 C11 Br1 119.4(7) . . ?
O2 C7 O1 125.1(9) . . ?
O2 C7 C4 123.8(9) . . ?
O1 C7 C4 111.0(8) . . ?
C1 C6 C5 119.0(9) . . ?
C1 C6 H016 120.5 . . ?
C5 C6 H016 120.5 . . ?
C7 O1 C8 118.6(7) . . ?
Br4 Br2 Br3 155.8(10) . . ?
Br4 Br2 C1 105.5(8) . . ?
Br3 Br2 C1 98.7(8) . . ?
Br2 Br3 Br4 11.3(5) . . ?
Br2 Br3 C1 51.2(6) . . ?
Br4 Br3 C1 62.5(6) . . ?
Br2 Br4 Br3 12.9(6) . . ?
Br2 Br4 C1 49.3(7) . . ?
Br3 Br4 C1 62.2(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 C4 C3 C2 1.3(17) . . . . ?
C7 C4 C3 C2 177.5(10) . . . . ?
C1 C2 C3 C4 -0.6(16) . . . . ?
C3 C4 C5 C6 -1.7(17) . . . . ?
C7 C4 C5 C6 -177.8(11) . . . . ?
C8 C13 C12 C11 -1.6(15) . . . . ?
C3 C2 C1 C6 0.2(17) . . . . ?
C3 C2 C1 Br2 -178.9(9) . . . . ?
C3 C2 C1 Br3 176.0(14) . . . . ?
C3 C2 C1 Br4 -177.1(11) . . . . ?
C8 C9 C10 C11 1.1(16) . . . . ?
C12 C13 C8 C9 2.3(15) . . . . ?
C12 C13 C8 O1 177.8(9) . . . . ?
C10 C9 C8 C13 -2.1(16) . . . . ?
C10 C9 C8 O1 -177.8(9) . . . . ?
C9 C10 C11 C12 -0.5(16) . . . . ?
C9 C10 C11 Br1 -178.6(8) . . . . ?
C13 C12 C11 C10 0.8(15) . . . . ?
C13 C12 C11 Br1 178.9(7) . . . . ?
C5 C4 C7 O2 166.7(12) . . . . ?
C3 C4 C7 O2 -9.5(16) . . . . ?
C5 C4 C7 O1 -10.2(15) . . . . ?
C3 C4 C7 O1 173.6(9) . . . . ?
C2 C1 C6 C5 -0.6(18) . . . . ?
Br2 C1 C6 C5 178.5(9) . . . . ?
Br3 C1 C6 C5 -178.3(11) . . . . ?
Br4 C1 C6 C5 174.7(13) . . . . ?
C4 C5 C6 C1 1.3(18) . . . . ?
O2 C7 O1 C8 0.3(16) . . . . ?
C4 C7 O1 C8 177.0(9) . . . . ?
C13 C8 O1 C7 58.1(13) . . . . ?
C9 C8 O1 C7 -126.1(10) . . . . ?
C2 C1 Br2 Br4 4.1(14) . . . . ?
C6 C1 Br2 Br4 -175.0(13) . . . . ?
Br3 C1 Br2 Br4 178.5(15) . . . . ?
C2 C1 Br2 Br3 -174.4(12) . . . . ?
C6 C1 Br2 Br3 6.5(14) . . . . ?
Br4 C1 Br2 Br3 -178.5(15) . . . . ?
C1 Br2 Br3 Br4 176(3) . . . . ?
Br4 Br2 Br3 C1 -176(3) . . . . ?
C1 Br2 Br4 Br3 -176(4) . . . . ?
Br3 Br2 Br4 C1 176(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H008 O2 0.95 2.39 3.240(12) 149.2 4_565
C9 H011 Br3 0.95 2.60 3.493(17) 157.3 3_645
C10 H012 Br4 0.95 2.53 3.430(18) 158.2 1_445

_refine_diff_density_max         0.631
_refine_diff_density_min         -0.856
_refine_diff_density_rms         0.133

_shelxl_version_number           2014-3

