# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
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# 
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#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_cd214181

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 Br2 O4'
_chemical_formula_weight         506.18

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   5.9442(10)
_cell_length_b                   6.7813(11)
_cell_length_c                   13.014(2)
_cell_angle_alpha                91.341(3)
_cell_angle_beta                 92.608(3)
_cell_angle_gamma                105.719(3)
_cell_volume                     504.10(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1516
_cell_measurement_theta_min      6.246
_cell_measurement_theta_max      56.389

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_F_000             252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    4.046
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4198
_exptl_absorpt_correction_T_max  0.7456
_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            3040
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.567
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             1980
_reflns_number_gt                1631
_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)+(0.0710P)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       0.013(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1980
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1174
_refine_ls_wR_factor_gt          0.1109
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 1.29360(7) 0.80578(5) 1.07440(2) 0.0623(2) Uani 1 1 d . . . . .
O1 O 0.8753(4) 0.0991(3) 0.6327(2) 0.0615(7) Uani 1 1 d . . . . .
O2 O 0.5985(3) 0.2588(3) 0.6453(2) 0.0489(6) Uani 1 1 d . . . . .
C1 C 1.0549(4) 0.3921(4) 0.4506(2) 0.0298(6) Uani 1 1 d . . . . .
H1 H 1.0373 0.2453 0.4390 0.036 Uiso 1 1 calc R U . . .
C2 C 1.1534(5) 0.5097(4) 0.5489(2) 0.0292(6) Uani 1 1 d . . . . .
H2 H 1.3177 0.5879 0.5606 0.035 Uiso 1 1 calc R U . . .
C3 C 0.9810(4) 0.4671(4) 0.6321(2) 0.0296(6) Uani 1 1 d . . . . .
C4 C 0.8177(5) 0.2537(4) 0.6358(2) 0.0330(6) Uani 1 1 d . . . . .
C5 C 0.4285(6) 0.0622(6) 0.6553(4) 0.0640(12) Uani 1 1 d . . . . .
H5A H 0.4026 -0.0126 0.5903 0.096 Uiso 1 1 calc R U . . .
H5B H 0.2838 0.0838 0.6760 0.096 Uiso 1 1 calc R U . . .
H5C H 0.4866 -0.0146 0.7061 0.096 Uiso 1 1 calc R U . . .
C6 C 1.0649(5) 0.5616(4) 0.7378(2) 0.0309(6) Uani 1 1 d . . . . .
C7 C 0.9486(6) 0.6825(5) 0.7877(3) 0.0431(7) Uani 1 1 d . . . . .
H7 H 0.8222 0.7140 0.7539 0.052 Uiso 1 1 calc R U . . .
C8 C 1.0171(6) 0.7578(5) 0.8874(3) 0.0504(8) Uani 1 1 d . . . . .
H8 H 0.9368 0.8386 0.9206 0.060 Uiso 1 1 calc R U . . .
C9 C 1.2042(5) 0.7122(4) 0.9364(2) 0.0414(7) Uani 1 1 d . . . . .
C10 C 1.3279(6) 0.5985(6) 0.8873(3) 0.0487(8) Uani 1 1 d . . . . .
H10 H 1.4586 0.5724 0.9201 0.058 Uiso 1 1 calc R U . . .
C11 C 1.2550(6) 0.5226(5) 0.7877(2) 0.0447(7) Uani 1 1 d . . . . .
H11 H 1.3371 0.4436 0.7542 0.054 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 C9 1.894(3) . ?
O1 C4 1.188(3) . ?
O2 C4 1.324(3) . ?
O2 C5 1.451(4) . ?
C1 C2 1.499(4) . ?
C1 C3 1.500(4) 2_766 ?
C1 C2 1.557(4) 2_766 ?
C1 H1 0.9800 . ?
C2 C3 1.504(4) . ?
C2 C1 1.557(4) 2_766 ?
C2 H2 0.9800 . ?
C3 C1 1.500(4) 2_766 ?
C3 C6 1.508(4) . ?
C3 C4 1.512(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C11 1.368(4) . ?
C6 C7 1.377(4) . ?
C7 C8 1.385(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.368(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.367(4) . ?
C10 C11 1.390(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?

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
C4 O2 C5 116.0(3) . . ?
C2 C1 C3 111.2(2) . 2_766 ?
C2 C1 C2 89.3(2) . 2_766 ?
C3 C1 C2 58.90(17) 2_766 2_766 ?
C2 C1 H1 124.1 . . ?
C3 C1 H1 124.1 2_766 . ?
C2 C1 H1 124.1 2_766 . ?
C1 C2 C3 111.9(2) . . ?
C1 C2 C1 90.7(2) . 2_766 ?
C3 C2 C1 58.67(17) . 2_766 ?
C1 C2 H2 123.7 . . ?
C3 C2 H2 123.7 . . ?
C1 C2 H2 123.7 2_766 . ?
C1 C3 C2 62.43(18) 2_766 . ?
C1 C3 C6 117.5(2) 2_766 . ?
C2 C3 C6 117.4(2) . . ?
C1 C3 C4 120.3(2) 2_766 . ?
C2 C3 C4 118.2(2) . . ?
C6 C3 C4 112.6(2) . . ?
O1 C4 O2 123.2(3) . . ?
O1 C4 C3 125.3(3) . . ?
O2 C4 C3 111.4(2) . . ?
O2 C5 H5A 109.5 . . ?
O2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C6 C7 118.5(3) . . ?
C11 C6 C3 120.3(2) . . ?
C7 C6 C3 121.2(3) . . ?
C6 C7 C8 121.0(3) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 119.3(3) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 Br1 119.2(2) . . ?
C8 C9 Br1 119.9(2) . . ?
C9 C10 C11 118.9(3) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C6 C11 C10 121.4(3) . . ?
C6 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?

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
C3 C1 C2 C3 112.3(2) 2_766 . . . ?
C2 C1 C2 C3 56.3(2) 2_766 . . . ?
C3 C1 C2 C1 56.0(2) 2_766 . . 2_766 ?
C2 C1 C2 C1 0.002(0) 2_766 . . 2_766 ?
C1 C2 C3 C1 -76.7(2) . . . 2_766 ?
C1 C2 C3 C6 174.9(2) . . . . ?
C1 C2 C3 C6 -108.4(3) 2_766 . . . ?
C1 C2 C3 C4 34.7(3) . . . . ?
C1 C2 C3 C4 111.4(3) 2_766 . . . ?
C5 O2 C4 O1 1.9(5) . . . . ?
C5 O2 C4 C3 -176.8(3) . . . . ?
C1 C3 C4 O1 122.2(3) 2_766 . . . ?
C2 C3 C4 O1 49.3(4) . . . . ?
C6 C3 C4 O1 -92.6(4) . . . . ?
C1 C3 C4 O2 -59.1(3) 2_766 . . . ?
C2 C3 C4 O2 -132.0(3) . . . . ?
C6 C3 C4 O2 86.0(3) . . . . ?
C1 C3 C6 C11 -128.6(3) 2_766 . . . ?
C2 C3 C6 C11 -57.2(4) . . . . ?
C4 C3 C6 C11 85.1(3) . . . . ?
C1 C3 C6 C7 53.6(4) 2_766 . . . ?
C2 C3 C6 C7 125.1(3) . . . . ?
C4 C3 C6 C7 -92.6(3) . . . . ?
C11 C6 C7 C8 -2.1(5) . . . . ?
C3 C6 C7 C8 175.7(3) . . . . ?
C6 C7 C8 C9 0.5(5) . . . . ?
C7 C8 C9 C10 1.9(5) . . . . ?
C7 C8 C9 Br1 -177.8(2) . . . . ?
C8 C9 C10 C11 -2.5(5) . . . . ?
Br1 C9 C10 C11 177.1(3) . . . . ?
C7 C6 C11 C10 1.4(5) . . . . ?
C3 C6 C11 C10 -176.4(3) . . . . ?
C9 C10 C11 C6 0.9(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C5 H5B O1 0.96 2.50 3.365(5) 150.2 1_455
C8 H8 Br1 0.93 3.08 3.924(3) 151.7 2_777

_refine_diff_density_max         0.525
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.124

_shelxl_version_number           2013-4



_database_code_depnum_ccdc_archive 'CCDC 1004894'
