# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1531429'
_audit_update_record             
;
2017-02-07 deposited with the CCDC.
2017-05-03 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 Br2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         322.00

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   20.362(2)
_cell_length_b                   6.3138(7)
_cell_length_c                   16.3787(18)
_cell_angle_alpha                90
_cell_angle_beta                 95.2864(16)
_cell_angle_gamma                90
_cell_volume                     2096.7(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2478
_cell_measurement_theta_min      2.4977
_cell_measurement_theta_max      27.2970
_cell_measurement_temperature    173

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    2.040
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248

_exptl_absorpt_coefficient_mu    7.702
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_absorpt_correction_T_min  0.36
_exptl_absorpt_correction_T_max  0.51

_exptl_special_details           'SADABS (Sheldrick 1996)'

_diffrn_ambient_temperature      173

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            11379
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_theta_min         1.00
_diffrn_reflns_theta_max         27.462
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       21

_refine_special_details          
;
;

_reflns_number_total             4737
_reflns_number_gt                3424
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_gt          0.0572
_refine_ls_wR_factor_ref         0.0635
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_number_reflns         4737
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0120P)²+2.4177P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.554
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.18130(2) 0.67243(7) 0.40583(2) 0.02440(11) Uani d . . . 1 . .
Br Br3 0.31794(2) 0.16737(7) 0.36559(3) 0.02691(11) Uani d . . . 1 . .
Br Br2 0.13175(2) 1.09862(7) 0.47838(2) 0.02636(11) Uani d . . . 1 . .
Br Br4 0.36963(2) 0.59322(7) 0.44766(3) 0.02850(12) Uani d . . . 1 . .
O O3 0.46207(13) 0.1842(4) 0.30285(15) 0.0215(6) Uani d . . . 1 . .
O O4 0.47956(13) 0.5369(4) 0.33826(16) 0.0221(7) Uani d . . . 1 . .
H H4 0.4974 0.5782 0.2968 0.033 Uiso calc U . R 1 . .
O O2 0.02139(13) 1.0522(5) 0.34337(15) 0.0217(7) Uani d . . . 1 . .
H H2 0.0049 1.0983 0.2979 0.033 Uiso calc U . R 1 . .
O O1 0.03659(12) 0.6980(4) 0.31137(15) 0.0197(6) Uani d . . . 1 . .
C C14 0.4839(2) 0.0920(7) 0.3819(2) 0.0248(10) Uani d . . . 1 . .
H H14A 0.5323 0.1066 0.3934 0.03 Uiso calc U . R 1 . .
H H14B 0.4724 -0.0603 0.3829 0.03 Uiso calc U . R 1 . .
C C1 0.06806(18) 0.8952(6) 0.3306(2) 0.0158(8) Uani d . . . 1 . .
C C12 0.39663(18) 0.3405(6) 0.3932(2) 0.0181(9) Uani d . . . 1 . .
C C8 0.18785(19) 1.0687(8) 0.1390(3) 0.0272(10) Uani d . . . 1 . .
H H8 0.214 1.1081 0.0963 0.033 Uiso calc U . R 1 . .
C C10 0.13492(19) 1.1586(7) 0.2589(2) 0.0232(9) Uani d . . . 1 . .
H H10 0.1249 1.2602 0.2987 0.028 Uiso calc U . R 1 . .
C C6 0.12592(18) 0.8071(7) 0.2050(2) 0.0194(9) Uani d . . . 1 . .
H H6 0.1103 0.6656 0.2077 0.023 Uiso calc U . R 1 . .
C C18 0.31212(19) 0.5651(7) 0.0964(2) 0.0266(10) Uani d . . . 1 . .
H H18 0.2856 0.6065 0.0483 0.032 Uiso calc U . R 1 . .
C C2 0.10349(18) 0.8485(6) 0.4170(2) 0.0158(8) Uani d . . . 1 . .
C C3 0.05144(19) 0.7228(7) 0.4572(2) 0.0206(9) Uani d . . . 1 . .
H H3A 0.0214 0.8179 0.4843 0.025 Uiso calc U . R 1 . .
H H3B 0.072 0.6218 0.4982 0.025 Uiso calc U . R 1 . .
C C20 0.37252(18) 0.2980(7) 0.1759(2) 0.0200(9) Uani d . . . 1 . .
H H20 0.387 0.1554 0.1821 0.024 Uiso calc U . R 1 . .
C C4 0.0149(2) 0.6067(7) 0.3853(2) 0.0240(10) Uani d . . . 1 . .
H H4A 0.0253 0.4535 0.3881 0.029 Uiso calc U . R 1 . .
H H4B -0.0333 0.6245 0.3862 0.029 Uiso calc U . R 1 . .
C C16 0.36770(18) 0.6511(7) 0.2278(2) 0.0231(10) Uani d . . . 1 . .
H H16 0.3793 0.7527 0.2695 0.028 Uiso calc U . R 1 . .
C C7 0.16428(19) 0.8663(7) 0.1428(2) 0.0239(10) Uani d . . . 1 . .
H H7 0.1742 0.7655 0.1027 0.029 Uiso calc U . R 1 . .
C C9 0.1736(2) 1.2161(7) 0.1975(3) 0.0272(10) Uani d . . . 1 . .
H H9 0.1904 1.3561 0.1954 0.033 Uiso calc U . R 1 . .
C C11 0.43168(18) 0.3833(6) 0.3147(2) 0.0167(9) Uani d . . . 1 . .
C C19 0.33412(19) 0.3601(7) 0.1054(2) 0.0225(10) Uani d . . . 1 . .
H H19 0.323 0.2599 0.0632 0.027 Uiso calc U . R 1 . .
C C13 0.44852(19) 0.2132(7) 0.4454(2) 0.0214(9) Uani d . . . 1 . .
H H13A 0.4793 0.3076 0.4785 0.026 Uiso calc U . R 1 . .
H H13B 0.4277 0.115 0.4825 0.026 Uiso calc U . R 1 . .
C C15 0.38969(18) 0.4451(6) 0.2373(2) 0.0168(9) Uani d . . . 1 . .
C C5 0.11041(17) 0.9534(6) 0.2630(2) 0.0161(9) Uani d . . . 1 . .
C C17 0.3287(2) 0.7100(7) 0.1576(3) 0.0278(10) Uani d . . . 1 . .
H H17 0.3133 0.8517 0.1517 0.033 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C2 . 1.957(4) ?
Br3 C12 . 1.958(4) ?
Br2 C2 . 1.932(4) ?
Br4 C12 . 1.932(4) ?
O3 C11 . 1.422(4) ?
O3 C14 . 1.452(4) ?
O4 C11 . 1.404(4) ?
O4 H4 . 0.84 ?
O2 C1 . 1.402(4) ?
O2 H2 . 0.84 ?
O1 C1 . 1.422(4) ?
O1 C4 . 1.446(4) ?
C14 C13 . 1.524(5) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C1 C5 . 1.511(5) ?
C1 C2 . 1.555(5) ?
C12 C13 . 1.526(5) ?
C12 C11 . 1.550(5) ?
C8 C7 . 1.369(6) ?
C8 C9 . 1.384(6) ?
C8 H8 . 0.95 ?
C10 C9 . 1.382(5) ?
C10 C5 . 1.392(6) ?
C10 H10 . 0.95 ?
C6 C5 . 1.382(5) ?
C6 C7 . 1.391(5) ?
C6 H6 . 0.95 ?
C18 C19 . 1.373(6) ?
C18 C17 . 1.376(6) ?
C18 H18 . 0.95 ?
C2 C3 . 1.522(5) ?
C3 C4 . 1.523(5) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C20 C15 . 1.389(5) ?
C20 C19 . 1.390(5) ?
C20 H20 . 0.95 ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C16 C15 . 1.379(6) ?
C16 C17 . 1.386(5) ?
C16 H16 . 0.95 ?
C7 H7 . 0.95 ?
C9 H9 . 0.95 ?
C11 C15 . 1.513(5) ?
C19 H19 . 0.95 ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C17 H17 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 O3 C14 . . 109.5(3) ?
C11 O4 H4 . . 109.5 ?
C1 O2 H2 . . 109.5 ?
C1 O1 C4 . . 109.2(3) ?
O3 C14 C13 . . 106.4(3) ?
O3 C14 H14A . . 110.5 ?
C13 C14 H14A . . 110.5 ?
O3 C14 H14B . . 110.5 ?
C13 C14 H14B . . 110.5 ?
H14A C14 H14B . . 108.6 ?
O2 C1 O1 . . 110.8(3) ?
O2 C1 C5 . . 112.2(3) ?
O1 C1 C5 . . 109.0(3) ?
O2 C1 C2 . . 105.2(3) ?
O1 C1 C2 . . 101.4(3) ?
C5 C1 C2 . . 117.7(3) ?
C13 C12 C11 . . 102.1(3) ?
C13 C12 Br4 . . 112.8(3) ?
C11 C12 Br4 . . 114.3(3) ?
C13 C12 Br3 . . 110.2(3) ?
C11 C12 Br3 . . 109.6(2) ?
Br4 C12 Br3 . . 107.81(18) ?
C7 C8 C9 . . 120.0(4) ?
C7 C8 H8 . . 120.0 ?
C9 C8 H8 . . 120.0 ?
C9 C10 C5 . . 120.7(4) ?
C9 C10 H10 . . 119.6 ?
C5 C10 H10 . . 119.6 ?
C5 C6 C7 . . 120.2(4) ?
C5 C6 H6 . . 119.9 ?
C7 C6 H6 . . 119.9 ?
C19 C18 C17 . . 119.5(4) ?
C19 C18 H18 . . 120.2 ?
C17 C18 H18 . . 120.2 ?
C3 C2 C1 . . 102.1(3) ?
C3 C2 Br2 . . 112.7(2) ?
C1 C2 Br2 . . 114.2(3) ?
C3 C2 Br1 . . 110.3(3) ?
C1 C2 Br1 . . 109.6(2) ?
Br2 C2 Br1 . . 107.94(17) ?
C2 C3 C4 . . 103.0(3) ?
C2 C3 H3A . . 111.2 ?
C4 C3 H3A . . 111.2 ?
C2 C3 H3B . . 111.2 ?
C4 C3 H3B . . 111.2 ?
H3A C3 H3B . . 109.1 ?
C15 C20 C19 . . 119.8(4) ?
C15 C20 H20 . . 120.1 ?
C19 C20 H20 . . 120.1 ?
O1 C4 C3 . . 106.9(3) ?
O1 C4 H4A . . 110.3 ?
C3 C4 H4A . . 110.3 ?
O1 C4 H4B . . 110.3 ?
C3 C4 H4B . . 110.3 ?
H4A C4 H4B . . 108.6 ?
C15 C16 C17 . . 120.1(4) ?
C15 C16 H16 . . 120.0 ?
C17 C16 H16 . . 120.0 ?
C8 C7 C6 . . 120.5(4) ?
C8 C7 H7 . . 119.8 ?
C6 C7 H7 . . 119.8 ?
C10 C9 C8 . . 119.7(4) ?
C10 C9 H9 . . 120.1 ?
C8 C9 H9 . . 120.1 ?
O4 C11 O3 . . 110.4(3) ?
O4 C11 C15 . . 112.1(3) ?
O3 C11 C15 . . 109.5(3) ?
O4 C11 C12 . . 104.7(3) ?
O3 C11 C12 . . 101.4(3) ?
C15 C11 C12 . . 118.1(3) ?
C18 C19 C20 . . 120.5(4) ?
C18 C19 H19 . . 119.7 ?
C20 C19 H19 . . 119.7 ?
C14 C13 C12 . . 103.2(3) ?
C14 C13 H13A . . 111.1 ?
C12 C13 H13A . . 111.1 ?
C14 C13 H13B . . 111.1 ?
C12 C13 H13B . . 111.1 ?
H13A C13 H13B . . 109.1 ?
C16 C15 C20 . . 119.4(4) ?
C16 C15 C11 . . 119.3(3) ?
C20 C15 C11 . . 121.2(4) ?
C6 C5 C10 . . 118.9(4) ?
C6 C5 C1 . . 121.6(4) ?
C10 C5 C1 . . 119.6(4) ?
C18 C17 C16 . . 120.6(4) ?
C18 C17 H17 . . 119.7 ?
C16 C17 H17 . . 119.7 ?



