# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_10febbm
_database_code_depnum_ccdc_archive 'CCDC 1404444'
_audit_update_record             
;
2015-06-02 deposited with the CCDC.
2015-08-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 Br2 O3'
_chemical_formula_sum            'C14 H10 Br2 O3'
_chemical_formula_weight         386.04

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   'P n 21 a'

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

_cell_length_a                   7.871(5)
_cell_length_b                   11.094(5)
_cell_length_c                   15.506(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1354.0(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      28.5
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.894
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    5.987
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.3806
_exptl_absorpt_correction_T_max  0.4476
_exptl_absorpt_process_details   'SADABAS 2.10 (Bruker 2003)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8212
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_sigmaI/netI    0.0695
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         28.51
_reflns_number_total             2782
_reflns_number_gt                1865
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45  (Bruker, 2003)'
_computing_structure_solution    SIR-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'Diamond 2.1e'

_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 > 2sigma(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)+(0.0866P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.067(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_number_reflns         2782
_refine_ls_number_parameters     173
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1563
_refine_ls_wR_factor_gt          0.1135
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.04440(10) 0.76793(8) 0.89098(5) 0.0525(3) Uani 1 1 d . . .
Br2 Br 0.05338(12) 0.72890(8) 0.67684(6) 0.0625(4) Uani 1 1 d . . .
O3 O 0.2356(7) 0.9753(5) 0.9947(3) 0.0436(12) Uani 1 1 d . . .
O4 O 0.2887(7) 1.1656(5) 0.6575(3) 0.0485(13) Uani 1 1 d . . .
H4 H 0.2891 1.1424 0.6072 0.073 Uiso 1 1 calc R . .
O5 O -0.0061(7) 1.0745(5) 0.9698(3) 0.0437(13) Uani 1 1 d . . .
C6 C 0.2105(9) 1.0985(6) 0.7978(5) 0.0361(15) Uani 1 1 d . . .
C7 C 0.2529(9) 1.2186(7) 0.8344(4) 0.0402(16) Uani 1 1 d . . .
C8 C 0.1570(9) 1.0054(6) 0.8502(4) 0.0358(14) Uani 1 1 d . . .
C9 C 0.2311(9) 1.0757(6) 0.7093(4) 0.0352(15) Uani 1 1 d . . .
C10 C 0.1237(11) 0.8753(7) 0.7270(5) 0.0444(17) Uani 1 1 d . . .
C11 C 0.3672(11) 1.2295(8) 0.9037(4) 0.0479(18) Uani 1 1 d . . .
H11 H 0.4184 1.1610 0.9265 0.058 Uiso 1 1 calc R . .
C12 C 0.1859(11) 1.3234(7) 0.7982(6) 0.0474(18) Uani 1 1 d . . .
H12 H 0.1123 1.3180 0.7514 0.057 Uiso 1 1 calc R . .
C13 C 0.1147(10) 0.8914(7) 0.8162(5) 0.0402(16) Uani 1 1 d . . .
C14 C 0.3356(14) 1.4446(10) 0.9017(7) 0.070(3) Uani 1 1 d . . .
H14 H 0.3619 1.5198 0.9248 0.084 Uiso 1 1 calc R . .
C15 C 0.2284(14) 1.4358(8) 0.8313(6) 0.061(3) Uani 1 1 d . . .
H15 H 0.1846 1.5052 0.8061 0.073 Uiso 1 1 calc R . .
C16 C 0.1821(11) 0.9647(8) 0.6743(5) 0.0465(18) Uani 1 1 d . . .
H16 H 0.1894 0.9519 0.6152 0.056 Uiso 1 1 calc R . .
C17 C 0.1918(12) 0.9670(10) 1.0849(5) 0.055(2) Uani 1 1 d . . .
H17A H 0.2838 0.9303 1.1160 0.083 Uiso 1 1 calc R . .
H17B H 0.0912 0.9189 1.0914 0.083 Uiso 1 1 calc R . .
H17C H 0.1714 1.0463 1.1074 0.083 Uiso 1 1 calc R . .
C18 C 0.4035(13) 1.3410(10) 0.9377(6) 0.065(3) Uani 1 1 d . . .
H18 H 0.4745 1.3470 0.9855 0.078 Uiso 1 1 calc R . .
C19 C 0.1197(9) 1.0244(6) 0.9444(4) 0.0346(14) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0691(5) 0.0329(4) 0.0556(5) 0.0056(3) 0.0089(4) -0.0062(4)
Br2 0.0823(7) 0.0428(5) 0.0623(6) -0.0168(4) 0.0012(4) -0.0102(5)
O3 0.046(3) 0.045(3) 0.040(3) 0.008(2) -0.001(2) 0.009(2)
O4 0.067(4) 0.038(3) 0.041(3) 0.001(2) 0.015(2) -0.001(3)
O5 0.047(3) 0.046(3) 0.038(3) 0.000(2) 0.001(2) 0.009(2)
C6 0.038(4) 0.030(3) 0.041(4) 0.004(3) 0.002(3) 0.003(3)
C7 0.043(3) 0.033(4) 0.044(4) -0.001(3) 0.009(3) -0.011(3)
C8 0.044(4) 0.028(3) 0.036(4) 0.000(3) -0.002(3) 0.001(3)
C9 0.041(4) 0.035(4) 0.030(4) 0.001(3) 0.006(3) 0.002(3)
C10 0.055(4) 0.035(4) 0.044(4) -0.011(3) 0.006(3) -0.001(3)
C11 0.053(4) 0.048(5) 0.043(4) 0.000(3) 0.001(3) -0.014(4)
C12 0.056(5) 0.036(4) 0.050(4) -0.001(3) 0.004(4) 0.001(3)
C13 0.043(4) 0.034(4) 0.043(4) 0.003(3) -0.004(3) 0.003(3)
C14 0.096(8) 0.045(5) 0.068(6) -0.017(4) 0.029(6) -0.021(5)
C15 0.091(7) 0.035(5) 0.058(6) 0.002(4) 0.024(5) 0.004(4)
C16 0.055(5) 0.042(4) 0.043(4) -0.014(3) 0.006(3) -0.001(3)
C17 0.061(5) 0.065(6) 0.040(4) -0.001(4) -0.007(4) 0.007(4)
C18 0.067(6) 0.077(8) 0.052(5) -0.013(5) 0.009(5) -0.033(5)
C19 0.043(4) 0.029(3) 0.032(3) 0.003(3) 0.000(3) 0.002(3)

_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 C13 1.878(8) . ?
Br2 C10 1.884(8) . ?
O3 C19 1.318(8) . ?
O3 C17 1.444(9) . ?
O4 C9 1.359(9) . ?
O5 C19 1.202(9) . ?
C6 C8 1.379(10) . ?
C6 C9 1.405(9) . ?
C6 C7 1.485(10) . ?
C7 C12 1.395(11) . ?
C7 C11 1.406(11) . ?
C8 C13 1.410(10) . ?
C8 C19 1.505(10) . ?
C9 C16 1.399(11) . ?
C10 C16 1.365(12) . ?
C10 C13 1.396(10) . ?
C11 C18 1.375(13) . ?
C12 C15 1.389(12) . ?
C14 C18 1.385(16) . ?
C14 C15 1.384(15) . ?

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
C19 O3 C17 115.8(6) . . ?
C8 C6 C9 118.3(6) . . ?
C8 C6 C7 121.0(6) . . ?
C9 C6 C7 120.6(6) . . ?
C12 C7 C11 118.5(7) . . ?
C12 C7 C6 120.6(6) . . ?
C11 C7 C6 120.8(7) . . ?
C6 C8 C13 121.6(7) . . ?
C6 C8 C19 121.7(6) . . ?
C13 C8 C19 116.2(6) . . ?
O4 C9 C16 120.5(6) . . ?
O4 C9 C6 119.0(6) . . ?
C16 C9 C6 120.4(6) . . ?
C16 C10 C13 121.1(7) . . ?
C16 C10 Br2 118.6(5) . . ?
C13 C10 Br2 120.3(6) . . ?
C18 C11 C7 120.2(9) . . ?
C15 C12 C7 120.6(8) . . ?
C10 C13 C8 118.2(7) . . ?
C10 C13 Br1 122.2(6) . . ?
C8 C13 Br1 119.6(5) . . ?
C18 C14 C15 119.6(9) . . ?
C14 C15 C12 120.2(9) . . ?
C10 C16 C9 120.0(7) . . ?
C11 C18 C14 120.8(9) . . ?
O5 C19 O3 124.6(6) . . ?
O5 C19 C8 122.9(6) . . ?
O3 C19 C8 112.4(6) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.743
_refine_diff_density_min         -0.729
_refine_diff_density_rms         0.170
