# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_o076
_database_code_depnum_ccdc_archive 'CCDC 1533545'
_audit_update_record             
;
2017-02-18 deposited with the CCDC.
2017-07-20 downloaded from the CCDC.
;
_audit_creation_date             2015-10-05
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H6 Br2 O4'
_chemical_formula_sum            'C8 H6 Br2 O4'
_chemical_formula_weight         325.95
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C8 H6 Br2 O4'
_chemical_oxdiff_usercomment     'Koenig, Simeth'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.56023(6)
_cell_length_b                   16.31960(16)
_cell_length_c                   6.91885(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.8033(7)
_cell_angle_gamma                90
_cell_volume                     963.165(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11290
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      73.3800
_cell_measurement_theta_min      5.1720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    10.606
_exptl_absorpt_correction_T_max  0.800
_exptl_absorpt_correction_T_min  0.634
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light red'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.248
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 0 -4 0.0491
-2 -1 4 0.0504
0 10 -1 0.0894
0 -11 1 0.1387
0 -10 -1 0.1212
-5 3 -1 0.0747
5 -2 1 0.0970
5 3 1 0.0763
-4 0 -3 0.0926
-6 -1 1 0.0741
6 0 -1 0.0814
5 6 0 0.0708
1 4 -4 0.0531
4 1 3 0.0773
3 -3 -4 0.0664

_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.103
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.9926 -0.0015 -3.9998 -0.0272 -0.8992 -0.2548
-1.9924 -0.9975 3.9993 0.0262 0.9248 0.1640
-0.0036 9.9907 -0.9942 0.0898 -0.4571 0.8498
0.0038 -10.9897 0.9937 -0.0908 0.4828 -0.9406
0.0004 -9.9908 -1.0042 0.0699 0.0564 -0.9652
-4.9993 3.0002 -0.9902 0.9495 -0.0331 0.2745
4.9991 -2.0012 0.9907 -0.9485 0.0074 -0.1837
4.9981 2.9942 0.9932 -0.9435 -0.1210 0.2700
-4.0024 0.0022 -2.9916 0.9329 -0.4056 -0.1252
-5.9947 -0.9953 1.0077 0.9591 0.5192 0.0389
5.9949 -0.0038 -1.0082 -0.9601 -0.4935 -0.1296
4.9959 5.9914 -0.0045 -0.8606 -0.3984 0.4846
0.9923 3.9954 -3.9963 0.1501 -0.9530 0.1202
4.0022 0.9968 2.9921 -0.9319 0.3799 0.2159
2.9926 -2.9994 -4.0028 -0.2035 -0.8710 -0.5390

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            13822
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         73.474
_diffrn_reflns_theta_min         5.185
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 4.2047
_diffrn_detector_type            TitanS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  69.00   1.00    1.00    --   44.10 -37.00-120.00   97
  2  ω     13.00 118.00   1.00    1.00    --   44.10  77.00-150.00  105
  3  ω     35.00 131.00   1.00    1.00    --  104.50 -61.00 -60.00   96
  4  ω     21.00 109.00   1.00    1.00    --  104.50 -94.00 -60.00   88
  5  ω     78.00 174.00   1.00    1.00    --  104.50  61.00-180.00   96
  6  ω     31.00 121.00   1.00    1.00    --  104.50-125.00  60.00   90
  7  ω     80.00 175.00   1.00    1.00    --  104.50  45.00-180.00   95
  8  ω     34.00 129.00   1.00    1.00    --  104.50 -45.00  30.00   95
  9  ω     13.00 118.00   1.00    1.00    --   44.10  77.00   0.00  105
 10  ω     19.00 114.00   1.00    1.00    --   44.10  57.00 120.00   95
 11  ω     78.00 174.00   1.00    1.00    --  104.50  61.00   0.00   96
 12  ω     80.00 175.00   1.00    1.00    --  104.50  45.00 -90.00   95
 13  ω     21.00 109.00   1.00    1.00    --  104.50 -94.00-180.00   88
 14  ω     80.00 175.00   1.00    1.00    --  104.50  45.00  90.00   95
 15  ω    -26.00  70.00   1.00    1.00    --   44.10 -57.00  90.00   96
 16  ω     19.00 114.00   1.00    1.00    --   44.10  57.00 -60.00   95
 17  ω     80.00 175.00   1.00    1.00    --  104.50  45.00 -30.00   95
 18  ω     78.00 174.00   1.00    1.00    --  104.50  61.00 120.00   96
 19  ω     73.00 178.00   1.00    1.00    --  104.50  77.00-150.00  105
 20  ω     78.00 174.00   1.00    1.00    --  104.50  61.00  30.00   96
 21  ω     73.00 118.00   1.00    1.00    --   44.10 125.00 150.00   45
 22  ω     73.00 118.00   1.00    1.00    --   44.10 125.00 -30.00   45
 23  ω     73.00 178.00   1.00    1.00    --  104.50  77.00 -90.00  105
 24  ω     21.00  94.00   1.00    1.00    --  104.50 -94.00  90.00   73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'GV1000, TitanS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1735411000
_diffrn_orient_matrix_UB_12      0.0010051000
_diffrn_orient_matrix_UB_13      -0.0796528000
_diffrn_orient_matrix_UB_21      -0.0486074000
_diffrn_orient_matrix_UB_22      -0.0258111000
_diffrn_orient_matrix_UB_23      0.2005938000
_diffrn_orient_matrix_UB_31      -0.0118503000
_diffrn_orient_matrix_UB_32      0.0908044000
_diffrn_orient_matrix_UB_33      0.0577574000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'gradient vaccum rotating-anode X-ray tube'
_diffrn_source_type              'GV1000 (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1907
_reflns_number_total             1927
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.959
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1927
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0271
_refine_ls_restrained_S_all      1.191
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0342P)²+1.5180P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0685
_refine_ls_wR_factor_ref         0.0688
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C008(H00A,H00B,H00C), C00C(H00D,H00E,H00F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Br01 Br 0.36021(3) 0.44788(2) 0.25408(4) 0.01737(11) Uani 1 1 d . . . . .
Br02 Br 0.65142(4) 0.30633(2) 0.27231(5) 0.02433(11) Uani 1 1 d . . . . .
O003 O 0.5017(2) 0.61437(12) 0.2295(3) 0.0208(4) Uani 1 1 d . . . . .
O004 O 0.7963(2) 0.67233(11) 0.2289(3) 0.0162(4) Uani 1 1 d . . . . .
O005 O 1.0440(2) 0.54740(13) 0.2525(3) 0.0252(5) Uani 1 1 d . . . . .
O006 O 0.9619(2) 0.39535(13) 0.2671(3) 0.0252(4) Uani 1 1 d . . . . .
C007 C 0.5731(3) 0.47436(16) 0.2539(4) 0.0146(5) Uani 1 1 d . . . . .
C008 C 0.7777(3) 0.72053(16) 0.4007(4) 0.0184(5) Uani 1 1 d . . . . .
H00A H 0.8013 0.7769 0.3756 0.028 Uiso 1 1 calc GR . . . .
H00B H 0.8478 0.7006 0.5058 0.028 Uiso 1 1 calc GR . . . .
H00C H 0.6716 0.7162 0.4348 0.028 Uiso 1 1 calc GR . . . .
C009 C 0.6066(3) 0.56431(16) 0.2439(4) 0.0139(5) Uani 1 1 d . . . . .
C00A C 0.8896(3) 0.53506(17) 0.2538(4) 0.0163(5) Uani 1 1 d . . . . .
C00B C 0.7721(3) 0.59023(16) 0.2490(4) 0.0142(5) Uani 1 1 d . . . . .
C00C C 1.1073(3) 0.62892(17) 0.2343(5) 0.0236(6) Uani 1 1 d . . . . .
H00D H 1.0594 0.6544 0.1190 0.035 Uiso 1 1 calc GR . . . .
H00E H 1.2185 0.6256 0.2262 0.035 Uiso 1 1 calc GR . . . .
H00F H 1.0860 0.6609 0.3455 0.035 Uiso 1 1 calc GR . . . .
C00D C 0.8556(3) 0.44482(17) 0.2611(4) 0.0170(6) Uani 1 1 d . . . . .
C00E C 0.6881(3) 0.41875(16) 0.2614(4) 0.0157(5) 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
Br01 C007 1.873(3) . ?
Br02 C00E 1.864(3) . ?
O003 C009 1.212(3) . ?
O004 C008 1.445(3) . ?
O004 C00B 1.365(3) . ?
O005 C00A 1.338(3) . ?
O005 C00C 1.446(3) . ?
O006 C00D 1.214(3) . ?
C007 C009 1.498(4) . ?
C007 C00E 1.336(4) . ?
C008 H00A 0.9600 . ?
C008 H00B 0.9600 . ?
C008 H00C 0.9600 . ?
C009 C00B 1.476(4) . ?
C00A C00B 1.348(4) . ?
C00A C00D 1.503(4) . ?
C00C H00D 0.9600 . ?
C00C H00E 0.9600 . ?
C00C H00F 0.9600 . ?
C00D C00E 1.496(4) . ?

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
C00B O004 C008 115.00(19) . . ?
C00A O005 C00C 121.1(2) . . ?
C009 C007 Br01 114.59(19) . . ?
C00E C007 Br01 123.8(2) . . ?
C00E C007 C009 121.6(2) . . ?
O004 C008 H00A 109.5 . . ?
O004 C008 H00B 109.5 . . ?
O004 C008 H00C 109.5 . . ?
H00A C008 H00B 109.5 . . ?
H00A C008 H00C 109.5 . . ?
H00B C008 H00C 109.5 . . ?
O003 C009 C007 121.4(2) . . ?
O003 C009 C00B 120.8(2) . . ?
C00B C009 C007 117.8(2) . . ?
O005 C00A C00B 129.4(3) . . ?
O005 C00A C00D 110.0(2) . . ?
C00B C00A C00D 120.6(2) . . ?
O004 C00B C009 115.6(2) . . ?
C00A C00B O004 122.6(2) . . ?
C00A C00B C009 121.4(2) . . ?
O005 C00C H00D 109.5 . . ?
O005 C00C H00E 109.5 . . ?
O005 C00C H00F 109.5 . . ?
H00D C00C H00E 109.5 . . ?
H00D C00C H00F 109.5 . . ?
H00E C00C H00F 109.5 . . ?
O006 C00D C00A 120.4(2) . . ?
O006 C00D C00E 121.7(3) . . ?
C00E C00D C00A 117.8(2) . . ?
C007 C00E Br02 123.0(2) . . ?
C007 C00E C00D 120.6(2) . . ?
C00D C00E Br02 116.39(19) . . ?

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
Br01 C007 C009 O003 -2.7(3) . . . . ?
Br01 C007 C009 C00B 178.23(17) . . . . ?
Br01 C007 C00E Br02 0.2(3) . . . . ?
Br01 C007 C00E C00D -179.90(18) . . . . ?
O003 C009 C00B O004 -2.5(3) . . . . ?
O003 C009 C00B C00A -176.2(3) . . . . ?
O005 C00A C00B O004 4.4(4) . . . . ?
O005 C00A C00B C009 177.6(3) . . . . ?
O005 C00A C00D O006 0.9(4) . . . . ?
O005 C00A C00D C00E -179.4(2) . . . . ?
O006 C00D C00E Br02 0.2(3) . . . . ?
O006 C00D C00E C007 -179.7(3) . . . . ?
C007 C009 C00B O004 176.6(2) . . . . ?
C007 C009 C00B C00A 2.9(4) . . . . ?
C008 O004 C00B C009 77.4(3) . . . . ?
C008 O004 C00B C00A -109.0(3) . . . . ?
C009 C007 C00E Br02 -179.57(19) . . . . ?
C009 C007 C00E C00D 0.3(4) . . . . ?
C00A C00D C00E Br02 -179.59(19) . . . . ?
C00A C00D C00E C007 0.5(4) . . . . ?
C00B C00A C00D O006 -179.3(3) . . . . ?
C00B C00A C00D C00E 0.4(4) . . . . ?
C00C O005 C00A C00B -3.5(5) . . . . ?
C00C O005 C00A C00D 176.3(2) . . . . ?
C00D C00A C00B O004 -175.4(2) . . . . ?
C00D C00A C00B C009 -2.2(4) . . . . ?
C00E C007 C009 O003 177.1(3) . . . . ?
C00E C007 C009 C00B -2.0(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-10-02
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.629
_oxdiff_exptl_absorpt_empirical_full_min 0.764
