# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

 
data_as
 
_audit_creation_method            SHELXL-2013
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C24 H15 Br3 Cu3 O15' 
_chemical_formula_weight          973.71

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'
 'Cu'  'Cu'   0.3201   1.2651
 '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            12
_space_group_name_H-M_alt         'C 2/m'
_space_group_name_Hall            '-C 2y'
 
_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'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z'
 '-x, -y, -z'
 'x, -y, z'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z'
 
_cell_length_a                    14.042(9)
_cell_length_b                    18.453(11)
_cell_length_c                    17.330(11)
_cell_angle_alpha                 90
_cell_angle_beta                  110.124(7)
_cell_angle_gamma                 90
_cell_volume                      4216(4)
_cell_formula_units_Z             4
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     1268 
_cell_measurement_theta_min       2.5 
_cell_measurement_theta_max       19.4 
 
_exptl_crystal_description        block 
_exptl_crystal_colour             green
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ?              
_exptl_crystal_density_diffrn     1.534          
_exptl_crystal_F_000              1884
_exptl_transmission_factor_min    ?                                             
_exptl_transmission_factor_max    ?                                             
_exptl_crystal_size_max           ? 
_exptl_crystal_size_mid           ? 
_exptl_crystal_size_min           ? 
_exptl_absorpt_coefficient_mu     4.394
_shelx_estimated_absorpt_T_min    ? 
_shelx_estimated_absorpt_T_max    ? 
_exptl_absorpt_correction_type    ? 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       296(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?                       
_diffrn_measurement_device_type    'Bruker Smart Aepex CCD'  
_diffrn_measurement_method        ? 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             14678
_diffrn_reflns_av_unetI/netI      0.2057
_diffrn_reflns_av_R_equivalents   0.1840
_diffrn_reflns_limit_h_min        -16
_diffrn_reflns_limit_h_max        16
_diffrn_reflns_limit_k_min        -19
_diffrn_reflns_limit_k_max        21
_diffrn_reflns_limit_l_min        -20
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          1.251
_diffrn_reflns_theta_max          25.050
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.997
_diffrn_measured_fraction_theta_full  0.976
_diffrn_reflns_Laue_measured_fraction_max    0.997
_diffrn_reflns_Laue_measured_fraction_full   0.976
_diffrn_reflns_point_group_measured_fraction_max   0.997
_diffrn_reflns_point_group_measured_fraction_full  0.976
_reflns_number_total              3852
_reflns_number_gt                 1726
_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        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_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)+(0.0615P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.00052(13)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3852
_refine_ls_number_parameters      212
_refine_ls_number_restraints      346
_refine_ls_R_factor_all           0.1629
_refine_ls_R_factor_gt            0.0869
_refine_ls_wR_factor_ref          0.1925
_refine_ls_wR_factor_gt           0.1753
_refine_ls_goodness_of_fit_ref    1.022
_refine_ls_restrained_S_all       1.004
_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_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
O5 O 0.7432(6) 0.3693(4) 0.9852(5) 0.0385(19) Uani 1 1 d . U . . .
O7 O 0.5902(5) 0.2713(4) 0.9129(5) 0.0359(19) Uani 1 1 d . U . . .
O2 O 0.5725(5) 0.0739(4) 0.6095(4) 0.0338(18) Uani 1 1 d . U . . .
Br1 Br 0.25423(13) 0.31274(9) 0.64196(11) 0.0837(7) Uani 1 1 d . U . . .
Br2 Br 1.05548(19) 0.5000 0.82279(17) 0.0811(9) Uani 1 2 d S TU P . .
C1 C 0.4833(9) 0.0986(6) 0.5964(7) 0.032(2) Uani 1 1 d . U . . .
C2 C 0.4724(9) 0.1582(6) 0.6506(7) 0.038(2) Uani 1 1 d . U . . .
C3 C 0.3833(10) 0.1998(6) 0.6269(8) 0.048(3) Uani 1 1 d . U . . .
H3 H 0.3317 0.1911 0.5771 0.058 Uiso 1 1 calc R U . . .
C4 C 0.3737(9) 0.2523(7) 0.6771(8) 0.045(3) Uani 1 1 d . U . . .
C5 C 0.4463(9) 0.2641(7) 0.7534(8) 0.042(3) Uani 1 1 d . U . . .
H5 H 0.4360 0.2999 0.7876 0.051 Uiso 1 1 calc R U . . .
C6 C 0.5348(9) 0.2228(6) 0.7795(7) 0.036(2) Uani 1 1 d . U . . .
C7 C 0.5456(9) 0.1730(6) 0.7248(7) 0.037(2) Uani 1 1 d . U . . .
H7 H 0.6064 0.1476 0.7388 0.044 Uiso 1 1 calc R U . . .
C8 C 0.6147(9) 0.2350(6) 0.8615(8) 0.034(2) Uani 1 1 d . U . . .
C9 C 0.8106(9) 0.3656(6) 0.9530(7) 0.035(2) Uani 1 1 d . U . . .
C10 C 0.8493(8) 0.4345(6) 0.9303(7) 0.033(2) Uani 1 1 d . U . . .
C11 C 0.8113(12) 0.5000 0.9486(10) 0.034(3) Uani 1 2 d S TU P . .
H11 H 0.7615 0.5000 0.9727 0.041 Uiso 1 2 calc R U P . .
C12 C 0.9211(9) 0.4351(6) 0.8944(7) 0.040(3) Uani 1 1 d . U . . .
H12 H 0.9469 0.3914 0.8835 0.047 Uiso 1 1 calc R U . . .
C13 C 0.9571(13) 0.5000 0.8733(11) 0.044(3) Uani 1 2 d S TU P . .
Cu1 Cu 0.81334(10) 0.21313(7) 0.97463(9) 0.0284(4) Uani 1 1 d . U . . .
Cu2 Cu 0.39995(14) 0.0000 0.46009(12) 0.0281(6) Uani 1 2 d S TU P . .
O1 O 0.2385(8) 0.0000 0.4171(8) 0.058(4) Uani 1 2 d S TU P . .
H1A H 0.2165 0.0000 0.3639 0.087 Uiso 1 2 d R U P . .
H1B H 0.2175 0.0000 0.4587 0.087 Uiso 1 2 d R U P . .
O3 O 0.4052(5) 0.0755(4) 0.5408(5) 0.0364(18) Uani 1 1 d . U . . .
O4 O 0.6985(6) 0.2076(4) 0.8709(5) 0.0385(18) Uani 1 1 d . U . . .
O6 O 0.9090(7) 0.1433(6) 0.9317(6) 0.083(3) Uani 1 1 d . U . . .
H6 H 0.9451 0.1726 0.9196 0.125 Uiso 1 1 d R U . . .
H6A H 0.9263 0.1011 0.9436 0.100 Uiso 1 1 d R U . . .
O8 O 0.8520(5) 0.3072(4) 0.9423(5) 0.0335(17) Uani 1 1 d . 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
O5 C9 1.255(12) . ?
O5 Cu1 1.952(7) 7_657 ?
O7 C8 1.254(13) . ?
O7 Cu1 1.975(8) 7_657 ?
O2 C1 1.277(12) . ?
O2 Cu2 1.945(7) 5_656 ?
Br1 C4 1.931(12) . ?
Br2 C13 1.873(16) . ?
C1 O3 1.259(12) . ?
C1 C2 1.488(15) . ?
C2 C7 1.370(15) . ?
C2 C3 1.404(15) . ?
C3 C4 1.339(15) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(16) . ?
C5 C6 1.394(15) . ?
C5 H5 0.9300 . ?
C6 C7 1.366(14) . ?
C6 C8 1.493(16) . ?
C7 H7 0.9300 . ?
C8 O4 1.239(12) . ?
C9 O8 1.269(12) . ?
C9 C10 1.486(15) . ?
C10 C12 1.355(14) . ?
C10 C11 1.401(13) . ?
C11 C10 1.401(13) 6_565 ?
C11 H11 0.9300 . ?
C12 C13 1.397(13) . ?
C12 H12 0.9300 . ?
C13 C12 1.397(13) 6_565 ?
Cu1 O5 1.952(7) 7_657 ?
Cu1 O8 1.957(7) . ?
Cu1 O4 1.961(8) . ?
Cu1 O7 1.975(8) 7_657 ?
Cu1 O6 2.170(8) . ?
Cu1 Cu1 2.620(3) 7_657 ?
Cu2 O2 1.945(7) 5_656 ?
Cu2 O2 1.945(7) 2_656 ?
Cu2 O3 1.956(8) . ?
Cu2 O3 1.956(8) 6 ?
Cu2 O1 2.129(11) . ?
Cu2 Cu2 2.671(4) 5_656 ?
O1 H1A 0.8655 . ?
O1 H1B 0.8682 . ?
O6 H6 0.8159 . ?
O6 H6A 0.8215 . ?
 
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
C9 O5 Cu1 125.3(7) . 7_657 ?
C8 O7 Cu1 121.1(8) . 7_657 ?
C1 O2 Cu2 122.1(7) . 5_656 ?
O3 C1 O2 123.9(10) . . ?
O3 C1 C2 118.8(10) . . ?
O2 C1 C2 117.3(10) . . ?
C7 C2 C3 118.1(11) . . ?
C7 C2 C1 122.2(11) . . ?
C3 C2 C1 119.6(11) . . ?
C4 C3 C2 118.9(12) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 122.1(12) . . ?
C3 C4 Br1 118.9(10) . . ?
C5 C4 Br1 119.0(9) . . ?
C4 C5 C6 120.4(12) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 116.3(11) . . ?
C7 C6 C8 122.3(11) . . ?
C5 C6 C8 121.4(11) . . ?
C6 C7 C2 124.0(11) . . ?
C6 C7 H7 118.0 . . ?
C2 C7 H7 118.0 . . ?
O4 C8 O7 127.2(12) . . ?
O4 C8 C6 115.6(11) . . ?
O7 C8 C6 117.2(10) . . ?
O5 C9 O8 124.3(10) . . ?
O5 C9 C10 118.1(10) . . ?
O8 C9 C10 117.4(10) . . ?
C12 C10 C11 119.8(12) . . ?
C12 C10 C9 121.8(10) . . ?
C11 C10 C9 118.4(10) . . ?
C10 C11 C10 119.3(15) . 6_565 ?
C10 C11 H11 120.3 . . ?
C10 C11 H11 120.3 6_565 . ?
C10 C12 C13 121.4(12) . . ?
C10 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C12 118.0(15) . 6_565 ?
C12 C13 Br2 120.9(8) . . ?
C12 C13 Br2 120.9(8) 6_565 . ?
O5 Cu1 O8 168.6(3) 7_657 . ?
O5 Cu1 O4 88.8(3) 7_657 . ?
O8 Cu1 O4 90.3(3) . . ?
O5 Cu1 O7 89.2(3) 7_657 7_657 ?
O8 Cu1 O7 89.4(3) . 7_657 ?
O4 Cu1 O7 168.7(3) . 7_657 ?
O5 Cu1 O6 92.0(4) 7_657 . ?
O8 Cu1 O6 99.4(3) . . ?
O4 Cu1 O6 93.8(4) . . ?
O7 Cu1 O6 97.4(3) 7_657 . ?
O5 Cu1 Cu1 83.0(2) 7_657 7_657 ?
O8 Cu1 Cu1 85.6(2) . 7_657 ?
O4 Cu1 Cu1 84.0(2) . 7_657 ?
O7 Cu1 Cu1 84.7(2) 7_657 7_657 ?
O6 Cu1 Cu1 174.6(3) . 7_657 ?
O2 Cu2 O2 89.0(4) 5_656 2_656 ?
O2 Cu2 O3 167.2(3) 5_656 . ?
O2 Cu2 O3 88.7(3) 2_656 . ?
O2 Cu2 O3 88.7(3) 5_656 6 ?
O2 Cu2 O3 167.2(3) 2_656 6 ?
O3 Cu2 O3 90.8(5) . 6 ?
O2 Cu2 O1 101.4(3) 5_656 . ?
O2 Cu2 O1 101.4(3) 2_656 . ?
O3 Cu2 O1 91.4(3) . . ?
O3 Cu2 O1 91.4(3) 6 . ?
O2 Cu2 Cu2 85.6(2) 5_656 5_656 ?
O2 Cu2 Cu2 85.6(2) 2_656 5_656 ?
O3 Cu2 Cu2 81.7(2) . 5_656 ?
O3 Cu2 Cu2 81.7(2) 6 5_656 ?
O1 Cu2 Cu2 170.1(4) . 5_656 ?
Cu2 O1 H1A 108.7 . . ?
Cu2 O1 H1B 109.6 . . ?
H1A O1 H1B 141.8 . . ?
C1 O3 Cu2 126.7(7) . . ?
C8 O4 Cu1 122.9(8) . . ?
Cu1 O6 H6 102.0 . . ?
Cu1 O6 H6A 129.9 . . ?
H6 O6 H6A 122.5 . . ?
C9 O8 Cu1 121.8(7) . . ?
 
_refine_diff_density_max    1.296
_refine_diff_density_min   -0.900
_refine_diff_density_rms    0.171

_shelxl_version_number 2013-2

loop_
  _platon_squeeze_void_nr
  _platon_squeeze_void_average_x
  _platon_squeeze_void_average_y
  _platon_squeeze_void_average_z
  _platon_squeeze_void_volume
  _platon_squeeze_void_count_electrons
  _platon_squeeze_void_content
   1  0.000  0.000  0.009       845       230 ' '
   2  0.500  0.500  0.458       845       230 ' '
_platon_squeeze_void_probe_radius                  1.20
_platon_squeeze_details                           ?



