# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_as
_database_code_depnum_ccdc_archive 'CCDC 1500559'
_audit_update_record             
;
2016-08-23 deposited with the CCDC.
2016-11-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H15 Cu3 I3 O15'
_chemical_formula_weight         1114.68

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'
I I -0.4742 1.8119 '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                   14.453(14)
_cell_length_b                   18.753(18)
_cell_length_c                   17.444(17)
_cell_angle_alpha                90
_cell_angle_beta                 110.169(11)
_cell_angle_gamma                90
_cell_volume                     4438(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2365
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      23.75

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_F_000             2100
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    3.560
_shelx_estimated_absorpt_T_min   0.717
_shelx_estimated_absorpt_T_max   0.764
_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            15448
_diffrn_reflns_av_unetI/netI     0.1230
_diffrn_reflns_av_R_equivalents  0.1534
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.244
_diffrn_reflns_theta_max         25.046
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             4045
_reflns_number_gt                2457
_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)+(0.0885P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4045
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1050
_refine_ls_R_factor_gt           0.0664
_refine_ls_wR_factor_ref         0.1876
_refine_ls_wR_factor_gt          0.1686
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_restrained_S_all      0.987
_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
C1 C 1.0094(8) 0.0979(5) 0.4017(6) 0.029(2) Uani 1 1 d . . . . .
C2 C 1.0208(7) 0.1578(5) 0.3491(6) 0.029(2) Uani 1 1 d . . . . .
C3 C 0.9440(7) 0.1727(5) 0.2730(6) 0.028(2) Uani 1 1 d . . . . .
H3 H 0.8850 0.1475 0.2572 0.033 Uiso 1 1 calc R U . . .
C4 C 0.9593(8) 0.2241(5) 0.2251(6) 0.029(2) Uani 1 1 d . . . . .
C5 C 1.0466(8) 0.2646(6) 0.2478(6) 0.040(3) Uani 1 1 d . . . . .
H5 H 1.0572 0.2986 0.2129 0.048 Uiso 1 1 calc R U . . .
C6 C 1.1155(8) 0.2520(6) 0.3235(7) 0.045(3) Uani 1 1 d . . . . .
C7 C 1.1063(8) 0.1999(5) 0.3730(7) 0.037(3) Uani 1 1 d . . . . .
H7 H 1.1561 0.1917 0.4228 0.044 Uiso 1 1 calc R U . . .
C8 C 0.8796(8) 0.2354(5) 0.1379(6) 0.031(2) Uani 1 1 d . . . . .
C9 C 0.8087(7) 0.1330(6) -0.0428(6) 0.035(3) Uani 1 1 d . . . . .
C10 C 0.8088(11) 0.0000 -0.0437(10) 0.041(4) Uani 1 2 d S T P . .
H10 H 0.7620 0.0000 -0.0181 0.050 Uiso 1 2 calc R U P . .
C11 C 0.8441(7) 0.0647(5) -0.0630(6) 0.028(2) Uani 1 1 d . . . . .
C12 C 0.9155(8) 0.0640(5) -0.1007(7) 0.041(3) Uani 1 1 d . . . . .
H12 H 0.9381 0.1071 -0.1137 0.049 Uiso 1 1 calc R U . . .
C13 C 0.9539(11) 0.0000 -0.1195(9) 0.030(3) Uani 1 2 d S T P . .
Cu1 Cu 0.81309(9) 0.28529(6) -0.02471(7) 0.0261(3) Uani 1 1 d . . . . .
Cu2 Cu 1.09799(12) 0.0000 0.53766(10) 0.0238(4) Uani 1 2 d S T P . .
I1 I 1.24368(6) 0.31756(5) 0.36225(5) 0.0580(3) Uani 1 1 d . . . . .
I2 I 1.05452(11) 0.0000 -0.17934(9) 0.0636(4) Uani 1 2 d S T P . .
O1 O 1.2577(7) 0.0000 0.5731(6) 0.043(3) Uani 1 2 d S T P . .
H1A H 1.2839 0.0000 0.6252 0.065 Uiso 1 2 d R U P . .
H1B H 1.2734 0.0000 0.5304 0.065 Uiso 1 2 d R U P . .
O2 O 0.9113(7) 0.3491(6) -0.0663(5) 0.080(3) Uani 1 1 d . . . . .
H2A H 0.9038 0.3928 -0.0569 0.120 Uiso 1 1 d R U . . .
H2C H 0.9499 0.3290 -0.0872 0.120 Uiso 1 1 d R U . . .
O3 O 1.0854(5) 0.0752(4) 0.4557(4) 0.0397(18) Uani 1 1 d . . . . .
O4 O 0.9236(5) 0.0743(3) 0.3909(4) 0.0307(16) Uani 1 1 d . . . . .
O5 O 0.7978(5) 0.2080(4) 0.1286(5) 0.045(2) Uani 1 1 d . . . . .
O6 O 0.9057(5) 0.2693(4) 0.0865(4) 0.0389(18) Uani 1 1 d . . . . .
O7 O 0.8484(6) 0.1905(3) -0.0545(5) 0.0417(19) Uani 1 1 d . . . . .
O8 O 0.7389(6) 0.1297(4) -0.0128(5) 0.045(2) Uani 1 1 d . . . . .


_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
C1 O3 1.249(11) . ?
C1 O4 1.269(11) . ?
C1 C2 1.495(13) . ?
C2 C7 1.403(14) . ?
C2 C3 1.435(14) . ?
C3 C4 1.342(13) . ?
C3 H3 0.9300 . ?
C4 C5 1.407(14) . ?
C4 C8 1.574(13) . ?
C5 C6 1.373(14) . ?
C5 H5 0.9300 . ?
C6 C7 1.341(14) . ?
C6 I1 2.129(11) . ?
C7 H7 0.9300 . ?
C8 O5 1.248(12) . ?
C8 O6 1.257(12) . ?
C9 O7 1.271(12) . ?
C9 O8 1.287(12) . ?
C9 C11 1.468(13) . ?
C10 C11 1.401(12) . ?
C10 C11 1.401(12) 6 ?
C10 H10 0.9300 . ?
C11 C12 1.401(14) . ?
C12 C13 1.408(13) . ?
C12 H12 0.9300 . ?
C13 C12 1.408(13) 6 ?
C13 I2 2.061(14) . ?
Cu1 O6 1.964(7) . ?
Cu1 O5 1.966(8) 7_655 ?
Cu1 O7 1.969(7) . ?
Cu1 O8 1.968(8) 7_655 ?
Cu1 O2 2.165(8) . ?
Cu1 Cu1 2.628(3) 7_655 ?
Cu2 O4 1.964(7) 2_756 ?
Cu2 O4 1.964(7) 5_756 ?
Cu2 O3 1.971(7) 6 ?
Cu2 O3 1.971(7) . ?
Cu2 O1 2.174(10) . ?
Cu2 Cu2 2.680(4) 5_756 ?
O1 H1A 0.8552 . ?
O1 H1B 0.8499 . ?
O2 H2A 0.8500 . ?
O2 H2C 0.8534 . ?
O4 Cu2 1.964(7) 5_756 ?
O5 Cu1 1.966(8) 7_655 ?
O8 Cu1 1.968(8) 7_655 ?

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
O3 C1 O4 123.6(9) . . ?
O3 C1 C2 117.7(9) . . ?
O4 C1 C2 118.7(9) . . ?
C7 C2 C3 119.1(9) . . ?
C7 C2 C1 120.8(9) . . ?
C3 C2 C1 120.0(9) . . ?
C4 C3 C2 118.3(9) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 122.4(9) . . ?
C3 C4 C8 118.3(9) . . ?
C5 C4 C8 119.1(8) . . ?
C6 C5 C4 117.5(9) . . ?
C6 C5 H5 121.3 . . ?
C4 C5 H5 121.3 . . ?
C7 C6 C5 122.9(10) . . ?
C7 C6 I1 119.0(8) . . ?
C5 C6 I1 118.0(8) . . ?
C6 C7 C2 119.5(10) . . ?
C6 C7 H7 120.3 . . ?
C2 C7 H7 120.3 . . ?
O5 C8 O6 128.2(9) . . ?
O5 C8 C4 114.5(9) . . ?
O6 C8 C4 117.3(9) . . ?
O7 C9 O8 124.5(9) . . ?
O7 C9 C11 119.1(9) . . ?
O8 C9 C11 116.3(10) . . ?
C11 C10 C11 119.9(14) . 6 ?
C11 C10 H10 120.1 . . ?
C11 C10 H10 120.1 6 . ?
C12 C11 C10 119.5(10) . . ?
C12 C11 C9 119.7(9) . . ?
C10 C11 C9 120.7(10) . . ?
C11 C12 C13 122.1(9) . . ?
C11 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
C12 C13 C12 116.9(13) 6 . ?
C12 C13 I2 121.5(6) 6 . ?
C12 C13 I2 121.5(6) . . ?
O6 Cu1 O5 169.1(3) . 7_655 ?
O6 Cu1 O7 88.4(3) . . ?
O5 Cu1 O7 91.0(3) 7_655 . ?
O6 Cu1 O8 90.2(3) . 7_655 ?
O5 Cu1 O8 88.4(3) 7_655 7_655 ?
O7 Cu1 O8 169.4(3) . 7_655 ?
O6 Cu1 O2 96.5(3) . . ?
O5 Cu1 O2 94.4(3) 7_655 . ?
O7 Cu1 O2 98.7(4) . . ?
O8 Cu1 O2 91.9(4) 7_655 . ?
O6 Cu1 Cu1 85.0(2) . 7_655 ?
O5 Cu1 Cu1 84.1(2) 7_655 7_655 ?
O7 Cu1 Cu1 84.5(2) . 7_655 ?
O8 Cu1 Cu1 84.9(2) 7_655 7_655 ?
O2 Cu1 Cu1 176.5(3) . 7_655 ?
O4 Cu2 O4 90.4(4) 2_756 5_756 ?
O4 Cu2 O3 166.5(3) 2_756 6 ?
O4 Cu2 O3 87.5(3) 5_756 6 ?
O4 Cu2 O3 87.5(3) 2_756 . ?
O4 Cu2 O3 166.5(3) 5_756 . ?
O3 Cu2 O3 91.4(4) 6 . ?
O4 Cu2 O1 101.8(3) 2_756 . ?
O4 Cu2 O1 101.8(3) 5_756 . ?
O3 Cu2 O1 91.7(3) 6 . ?
O3 Cu2 O1 91.7(3) . . ?
O4 Cu2 Cu2 86.5(2) 2_756 5_756 ?
O4 Cu2 Cu2 86.5(2) 5_756 5_756 ?
O3 Cu2 Cu2 80.0(2) 6 5_756 ?
O3 Cu2 Cu2 80.0(2) . 5_756 ?
O1 Cu2 Cu2 168.1(3) . 5_756 ?
Cu2 O1 H1A 109.9 . . ?
Cu2 O1 H1B 109.3 . . ?
H1A O1 H1B 140.8 . . ?
Cu1 O2 H2A 109.1 . . ?
Cu1 O2 H2C 120.0 . . ?
H2A O2 H2C 130.9 . . ?
C1 O3 Cu2 128.9(7) . . ?
C1 O4 Cu2 121.0(6) . 5_756 ?
C8 O5 Cu1 121.9(7) . 7_655 ?
C8 O6 Cu1 120.8(7) . . ?
C9 O7 Cu1 123.4(7) . . ?
C9 O8 Cu1 122.6(7) . 7_655 ?

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
O3 C1 C2 C7 -17.4(14) . . . . ?
O4 C1 C2 C7 160.5(9) . . . . ?
O3 C1 C2 C3 162.4(9) . . . . ?
O4 C1 C2 C3 -19.7(14) . . . . ?
C7 C2 C3 C4 3.8(14) . . . . ?
C1 C2 C3 C4 -176.0(9) . . . . ?
C2 C3 C4 C5 -1.6(15) . . . . ?
C2 C3 C4 C8 174.1(8) . . . . ?
C3 C4 C5 C6 -2.8(16) . . . . ?
C8 C4 C5 C6 -178.4(10) . . . . ?
C4 C5 C6 C7 5.2(18) . . . . ?
C4 C5 C6 I1 -175.9(8) . . . . ?
C5 C6 C7 C2 -3.0(18) . . . . ?
I1 C6 C7 C2 178.1(8) . . . . ?
C3 C2 C7 C6 -1.6(15) . . . . ?
C1 C2 C7 C6 178.2(10) . . . . ?
C3 C4 C8 O5 17.3(13) . . . . ?
C5 C4 C8 O5 -167.0(10) . . . . ?
C3 C4 C8 O6 -161.7(9) . . . . ?
C5 C4 C8 O6 14.1(14) . . . . ?
C11 C10 C11 C12 -1(2) 6 . . . ?
C11 C10 C11 C9 -179.5(8) 6 . . . ?
O7 C9 C11 C12 -5.0(15) . . . . ?
O8 C9 C11 C12 175.9(9) . . . . ?
O7 C9 C11 C10 173.8(11) . . . . ?
O8 C9 C11 C10 -5.3(15) . . . . ?
C10 C11 C12 C13 -0.5(18) . . . . ?
C9 C11 C12 C13 178.3(11) . . . . ?
C11 C12 C13 C12 2(2) . . . 6 ?
C11 C12 C13 I2 177.4(9) . . . . ?
O4 C1 O3 Cu2 0.0(15) . . . . ?
C2 C1 O3 Cu2 177.8(6) . . . . ?
O3 C1 O4 Cu2 1.8(13) . . . 5_756 ?
C2 C1 O4 Cu2 -176.0(6) . . . 5_756 ?
O6 C8 O5 Cu1 -0.9(15) . . . 7_655 ?
C4 C8 O5 Cu1 -179.7(6) . . . 7_655 ?
O5 C8 O6 Cu1 0.2(15) . . . . ?
C4 C8 O6 Cu1 179.0(6) . . . . ?
O8 C9 O7 Cu1 2.4(15) . . . . ?
C11 C9 O7 Cu1 -176.7(7) . . . . ?
O7 C9 O8 Cu1 -3.1(14) . . . 7_655 ?
C11 C9 O8 Cu1 176.0(7) . . . 7_655 ?

_refine_diff_density_max         1.567
_refine_diff_density_min         -1.005
_refine_diff_density_rms         0.199


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 0.500 0.002 896 157 ' '
2 0.500 0.000 0.444 896 157 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?


_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_as
_database_code_depnum_ccdc_archive 'CCDC 1500560'
_audit_update_record             
;
2016-08-23 deposited with the CCDC.
2016-11-08 downloaded from the CCDC.
;

_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          ?

