# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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 1420110'
_audit_update_record             
;
2015-08-24 deposited with the CCDC.
2015-12-14 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H8 Br2 O2'
_chemical_formula_sum            'C20 H8 Br2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         440.08

_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                   3.8828(3)
_cell_length_b                   13.5879(11)
_cell_length_c                   14.1314(13)
_cell_angle_alpha                90
_cell_angle_beta                 95.032(6)
_cell_angle_gamma                90
_cell_volume                     742.69(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3311
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      27.18
_cell_measurement_temperature    300.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.525
_exptl_crystal_size_mid          0.146
_exptl_crystal_size_min          0.139
_exptl_crystal_density_diffrn    1.968
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428

_exptl_absorpt_coefficient_mu    5.467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.16
_exptl_absorpt_correction_T_max  0.52

_exptl_special_details           
;
;

_diffrn_ambient_temperature      300.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ImuS

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'

_diffrn_measurement_device_type  
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            5701
_diffrn_reflns_av_R_equivalents  0.0764
_diffrn_reflns_av_unetI/netI     0.0792
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             1408
_reflns_number_gt                1152
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1159
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_number_reflns         1408
_refine_ls_number_parameters     109
_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)+(0.0573P)²] 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         0.771
_refine_diff_density_min         -0.702
_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'
Br Br -0.2901 2.4595 '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'

_computing_data_collection       
'Bruker Instrument Service v2013.12.0.0 (Bruker AXS)'
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS)'
_computing_structure_solution    'SHELXTL V6.14 (Bruker AXS)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  
'PLATON V1.16 (Spek, 2009), SHELXTL V6.14 (Bruker AXS)'

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 0.18334(11) 1.00972(3) 0.65483(3) 0.0453(2) Uani d . . . 1 . .
C C1 0.2531(8) 0.8744(3) 0.6303(3) 0.0310(9) Uani d . . . 1 . .
C C2 0.3940(8) 0.8487(3) 0.5470(3) 0.0323(9) Uani d . . . 1 . .
H H2 0.4583 0.8961 0.5045 0.039 Uiso calc U . R 1 . .
C C3 0.4343(8) 0.7500(3) 0.5301(3) 0.0303(9) Uani d . . . 1 . .
C C4 0.3436(8) 0.6781(3) 0.5937(3) 0.0293(9) Uani d . . . 1 . .
C C5 0.2115(8) 0.7058(3) 0.6770(3) 0.0360(10) Uani d . . . 1 . .
H H5 0.1545 0.6587 0.7208 0.043 Uiso calc U . R 1 . .
C C6 0.1650(8) 0.8054(3) 0.6944(3) 0.0356(9) Uani d . . . 1 . .
H H6 0.0734 0.8252 0.75 0.043 Uiso calc U . R 1 . .
C C7 0.4137(8) 0.5795(3) 0.5550(3) 0.0293(9) Uani d . . . 1 . .
C C8 0.3629(10) 0.4860(3) 0.5891(3) 0.0318(9) Uani d . . . 1 . .
H H8 0.2731 0.476 0.6473 0.038 Uiso calc U . R 1 . .
C C9 0.4508(8) 0.4077(3) 0.5335(3) 0.0310(9) Uani d . . . 1 . .
C C10 0.5798(8) 0.7003(3) 0.4477(3) 0.0319(9) Uani d . . . 1 . .
O O1 0.7013(7) 0.7387(2) 0.3810(2) 0.0436(8) Uani d . . . 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.0489(3) 0.0333(4) 0.0556(4) 0.00694(16) 0.0157(2) -0.00410(19)
C1 0.0235(15) 0.027(2) 0.043(2) -0.0002(15) 0.0014(15) -0.0028(18)
C2 0.0320(17) 0.030(2) 0.036(2) -0.0028(15) 0.0067(16) 0.0031(18)
C3 0.0274(17) 0.034(2) 0.030(2) -0.0036(15) 0.0020(15) -0.0001(18)
C4 0.0253(15) 0.031(2) 0.032(2) -0.0014(15) 0.0028(15) 0.0006(17)
C5 0.0376(19) 0.035(3) 0.037(2) -0.0053(16) 0.0103(16) 0.0017(19)
C6 0.0364(18) 0.038(3) 0.033(2) 0.0015(17) 0.0086(16) -0.004(2)
C7 0.0264(16) 0.031(2) 0.030(2) -0.0025(15) 0.0025(14) -0.0025(17)
C8 0.0334(19) 0.035(3) 0.028(2) -0.0040(15) 0.0045(16) -0.0005(17)
C9 0.0276(16) 0.030(2) 0.036(2) -0.0017(15) 0.0022(15) 0.0014(18)
C10 0.0298(17) 0.034(2) 0.032(2) -0.0045(16) 0.0040(16) -0.0034(19)
O1 0.0584(17) 0.0350(18) 0.0402(18) -0.0053(14) 0.0206(15) 0.0036(15)

_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 C1 . 1.895(4) ?
C1 C6 . 1.368(5) ?
C1 C2 . 1.385(5) ?
C2 C3 . 1.373(5) ?
C2 H2 . 0.93 ?
C3 C4 . 1.393(5) ?
C3 C10 . 1.499(6) ?
C4 C5 . 1.378(6) ?
C4 C7 . 1.481(5) ?
C5 C6 . 1.390(6) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
C7 C8 . 1.379(5) ?
C7 C9 3_666 1.409(6) ?
C8 C9 . 1.383(5) ?
C8 H8 . 0.93 ?
C9 C7 3_666 1.409(6) ?
C9 C10 3_666 1.498(6) ?
C10 O1 . 1.209(4) ?
C10 C9 3_666 1.498(6) ?

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
C6 C1 C2 . . 122.0(4) ?
C6 C1 Br1 . . 119.7(3) ?
C2 C1 Br1 . . 118.3(3) ?
C3 C2 C1 . . 117.0(4) ?
C3 C2 H2 . . 121.5 ?
C1 C2 H2 . . 121.5 ?
C2 C3 C4 . . 122.2(4) ?
C2 C3 C10 . . 129.2(4) ?
C4 C3 C10 . . 108.6(4) ?
C5 C4 C3 . . 119.6(4) ?
C5 C4 C7 . . 131.0(4) ?
C3 C4 C7 . . 109.3(3) ?
C4 C5 C6 . . 118.7(4) ?
C4 C5 H5 . . 120.6 ?
C6 C5 H5 . . 120.6 ?
C1 C6 C5 . . 120.4(4) ?
C1 C6 H6 . . 119.8 ?
C5 C6 H6 . . 119.8 ?
C8 C7 C9 . 3_666 120.0(3) ?
C8 C7 C4 . . 131.9(4) ?
C9 C7 C4 3_666 . 108.1(3) ?
C7 C8 C9 . . 117.4(4) ?
C7 C8 H8 . . 121.3 ?
C9 C8 H8 . . 121.3 ?
C8 C9 C7 . 3_666 122.7(3) ?
C8 C9 C10 . 3_666 128.7(4) ?
C7 C9 C10 3_666 3_666 108.6(3) ?
O1 C10 C9 . 3_666 127.1(4) ?
O1 C10 C3 . . 127.6(4) ?
C9 C10 C3 3_666 . 105.2(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 1.5(5) ?
Br1 C1 C2 C3 . . . . -178.6(2) ?
C1 C2 C3 C4 . . . . -0.9(5) ?
C1 C2 C3 C10 . . . . -179.5(3) ?
C2 C3 C4 C5 . . . . -0.6(5) ?
C10 C3 C4 C5 . . . . 178.3(3) ?
C2 C3 C4 C7 . . . . 179.3(3) ?
C10 C3 C4 C7 . . . . -1.8(4) ?
C3 C4 C5 C6 . . . . 1.4(5) ?
C7 C4 C5 C6 . . . . -178.5(3) ?
C2 C1 C6 C5 . . . . -0.7(5) ?
Br1 C1 C6 C5 . . . . 179.4(3) ?
C4 C5 C6 C1 . . . . -0.8(5) ?
C5 C4 C7 C8 . . . . 1.4(6) ?
C3 C4 C7 C8 . . . . -178.5(4) ?
C5 C4 C7 C9 . . . 3_666 179.9(3) ?
C3 C4 C7 C9 . . . 3_666 0.0(4) ?
C9 C7 C8 C9 3_666 . . . 0.2(6) ?
C4 C7 C8 C9 . . . . 178.6(3) ?
C7 C8 C9 C7 . . . 3_666 -0.2(6) ?
C7 C8 C9 C10 . . . 3_666 -179.3(3) ?
C2 C3 C10 O1 . . . . 2.7(6) ?
C4 C3 C10 O1 . . . . -176.1(3) ?
C2 C3 C10 C9 . . . 3_666 -178.4(3) ?
C4 C3 C10 C9 . . . 3_666 2.8(4) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C2 H2 Br1 3_676 0.93 3.03 3.918(4) 159.9 ?
C6 H6 O1 4_476 0.93 2.60 3.374(5) 141.6 ?
