# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# 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_a50925b
_database_code_depnum_ccdc_archive 'CCDC 1439381'
_audit_update_record             
;
2015-11-28 deposited with the CCDC.
2016-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H11 Br O2'
_chemical_formula_weight         315.16

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   9.986(7)
_cell_length_b                   15.521(11)
_cell_length_c                   8.740(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.027(9)
_cell_angle_gamma                90
_cell_volume                     1329.6(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    861
_cell_measurement_theta_min      3.130
_cell_measurement_theta_max      26.119

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    3.085
_shelx_estimated_absorpt_T_min   0.344
_shelx_estimated_absorpt_T_max   0.525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.408
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5990
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.078
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2583
_reflns_number_gt                1689
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0536P)²] 
 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     SHELXL
_refine_ls_extinction_coef       0.0040(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2583
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0934
_refine_ls_wR_factor_gt          0.0878
_refine_ls_goodness_of_fit_ref   0.896
_refine_ls_restrained_S_all      0.896
_refine_ls_shift/su_max          0.001
_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
Br1 Br 0.59198(3) 0.25438(2) 0.42271(4) 0.06376(16) Uani 1 1 d . . . . .
O1 O 0.9262(2) 0.18373(10) 0.2510(2) 0.0565(5) Uani 1 1 d . . . . .
O2 O 0.7729(2) 0.11098(11) 0.3474(3) 0.0684(6) Uani 1 1 d . . . . .
C1 C 0.8136(3) 0.18031(16) 0.3165(3) 0.0516(7) Uani 1 1 d . . . . .
C2 C 0.7523(3) 0.26313(14) 0.3428(3) 0.0450(6) Uani 1 1 d . . . . .
C3 C 0.8028(3) 0.33897(15) 0.3060(3) 0.0451(6) Uani 1 1 d . . . . .
C4 C 0.9244(3) 0.33840(15) 0.2406(3) 0.0454(6) Uani 1 1 d . . . . .
C5 C 0.9875(3) 0.41285(16) 0.1953(3) 0.0567(7) Uani 1 1 d . . . . .
H5 H 0.9511 0.4667 0.2097 0.068 Uiso 1 1 calc R U . . .
C6 C 1.1013(3) 0.40701(19) 0.1307(4) 0.0640(8) Uani 1 1 d . . . . .
H6 H 1.1423 0.4572 0.1043 0.077 Uiso 1 1 calc R U . . .
C7 C 1.1570(3) 0.32791(19) 0.1036(4) 0.0634(8) Uani 1 1 d . . . . .
C8 C 1.0954(3) 0.25403(16) 0.1453(4) 0.0589(8) Uani 1 1 d . . . . .
H8 H 1.1304 0.2002 0.1278 0.071 Uiso 1 1 calc R U . . .
C9 C 0.9826(3) 0.26039(15) 0.2125(4) 0.0495(7) Uani 1 1 d . . . . .
C10 C 0.7337(3) 0.42206(15) 0.3273(3) 0.0451(6) Uani 1 1 d . . . . .
C11 C 0.7676(4) 0.47020(18) 0.4592(4) 0.0717(9) Uani 1 1 d . . . . .
H11 H 0.8395 0.4531 0.5374 0.086 Uiso 1 1 calc R U . . .
C12 C 0.6961(4) 0.5442(2) 0.4777(4) 0.0853(11) Uani 1 1 d . . . . .
H12 H 0.7200 0.5766 0.5684 0.102 Uiso 1 1 calc R U . . .
C13 C 0.5915(4) 0.5702(2) 0.3652(4) 0.0735(10) Uani 1 1 d . . . . .
H13 H 0.5430 0.6198 0.3791 0.088 Uiso 1 1 calc R U . . .
C14 C 0.5574(4) 0.5234(2) 0.2314(4) 0.0772(9) Uani 1 1 d . . . . .
H14 H 0.4864 0.5414 0.1530 0.093 Uiso 1 1 calc R U . . .
C15 C 0.6287(3) 0.44961(18) 0.2133(4) 0.0679(9) Uani 1 1 d . . . . .
H15 H 0.6052 0.4178 0.1220 0.082 Uiso 1 1 calc R U . . .
C16 C 1.2826(4) 0.3216(3) 0.0331(5) 0.0927(12) Uani 1 1 d . . . . .
H16A H 1.3620 0.3313 0.1124 0.139 Uiso 1 1 calc R U . . .
H16B H 1.2785 0.3643 -0.0472 0.139 Uiso 1 1 calc R U . . .
H16C H 1.2874 0.2653 -0.0108 0.139 Uiso 1 1 calc R U . . .


_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 C2 1.870(3) . ?
O1 C1 1.357(3) . ?
O1 C9 1.385(3) . ?
O2 C1 1.199(3) . ?
C1 C2 1.461(3) . ?
C2 C3 1.343(3) . ?
C3 C4 1.438(4) . ?
C3 C10 1.491(3) . ?
C4 C9 1.385(4) . ?
C4 C5 1.408(3) . ?
C5 C6 1.365(4) . ?
C6 C7 1.387(4) . ?
C7 C8 1.383(4) . ?
C7 C16 1.503(4) . ?
C8 C9 1.369(4) . ?
C10 C11 1.361(4) . ?
C10 C15 1.369(4) . ?
C11 C12 1.378(4) . ?
C12 C13 1.351(5) . ?
C13 C14 1.363(4) . ?
C14 C15 1.374(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
C1 O1 C9 123.0(2) . . ?
O2 C1 O1 118.3(2) . . ?
O2 C1 C2 125.8(3) . . ?
O1 C1 C2 116.0(2) . . ?
C3 C2 C1 123.1(3) . . ?
C3 C2 Br1 122.69(19) . . ?
C1 C2 Br1 114.15(19) . . ?
C2 C3 C4 118.3(2) . . ?
C2 C3 C10 121.6(2) . . ?
C4 C3 C10 120.1(2) . . ?
C9 C4 C5 116.3(3) . . ?
C9 C4 C3 119.4(2) . . ?
C5 C4 C3 124.3(2) . . ?
C6 C5 C4 120.9(3) . . ?
C5 C6 C7 121.5(3) . . ?
C8 C7 C6 118.4(3) . . ?
C8 C7 C16 120.2(3) . . ?
C6 C7 C16 121.4(3) . . ?
C9 C8 C7 119.8(2) . . ?
C8 C9 O1 116.6(2) . . ?
C8 C9 C4 123.1(2) . . ?
O1 C9 C4 120.3(3) . . ?
C11 C10 C15 118.5(3) . . ?
C11 C10 C3 122.3(3) . . ?
C15 C10 C3 119.2(2) . . ?
C10 C11 C12 120.4(3) . . ?
C13 C12 C11 120.6(3) . . ?
C12 C13 C14 119.8(3) . . ?
C13 C14 C15 119.5(3) . . ?
C10 C15 C14 121.2(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O1 C1 O2 -179.2(3) . . . . ?
C9 O1 C1 C2 0.9(4) . . . . ?
O2 C1 C2 C3 179.8(3) . . . . ?
O1 C1 C2 C3 -0.3(4) . . . . ?
O2 C1 C2 Br1 -3.2(4) . . . . ?
O1 C1 C2 Br1 176.73(19) . . . . ?
C1 C2 C3 C4 -1.3(4) . . . . ?
Br1 C2 C3 C4 -178.03(19) . . . . ?
C1 C2 C3 C10 177.0(2) . . . . ?
Br1 C2 C3 C10 0.2(4) . . . . ?
C2 C3 C4 C9 2.3(4) . . . . ?
C10 C3 C4 C9 -176.0(3) . . . . ?
C2 C3 C4 C5 179.3(3) . . . . ?
C10 C3 C4 C5 1.1(4) . . . . ?
C9 C4 C5 C6 -1.3(4) . . . . ?
C3 C4 C5 C6 -178.5(3) . . . . ?
C4 C5 C6 C7 1.6(5) . . . . ?
C5 C6 C7 C8 -0.7(5) . . . . ?
C5 C6 C7 C16 -179.7(3) . . . . ?
C6 C7 C8 C9 -0.4(5) . . . . ?
C16 C7 C8 C9 178.6(3) . . . . ?
C7 C8 C9 O1 179.9(3) . . . . ?
C7 C8 C9 C4 0.6(5) . . . . ?
C1 O1 C9 C8 -179.2(3) . . . . ?
C1 O1 C9 C4 0.1(4) . . . . ?
C5 C4 C9 C8 0.2(4) . . . . ?
C3 C4 C9 C8 177.5(3) . . . . ?
C5 C4 C9 O1 -179.0(2) . . . . ?
C3 C4 C9 O1 -1.7(4) . . . . ?
C2 C3 C10 C11 93.4(4) . . . . ?
C4 C3 C10 C11 -88.4(4) . . . . ?
C2 C3 C10 C15 -84.0(4) . . . . ?
C4 C3 C10 C15 94.2(3) . . . . ?
C15 C10 C11 C12 1.0(5) . . . . ?
C3 C10 C11 C12 -176.4(3) . . . . ?
C10 C11 C12 C13 -0.1(6) . . . . ?
C11 C12 C13 C14 -0.8(6) . . . . ?
C12 C13 C14 C15 0.9(6) . . . . ?
C11 C10 C15 C14 -0.9(5) . . . . ?
C3 C10 C15 C14 176.6(3) . . . . ?
C13 C14 C15 C10 0.0(5) . . . . ?

_refine_diff_density_max         0.324
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.062

_shelxl_version_number           2013-2



