# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_122
_audit_block_doi                 10.5517/cc1jbsf2
_database_code_depnum_ccdc_archive 'CCDC 1410544'
_audit_update_record             
;
2015-07-04 deposited with the CCDC.
2015-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H20 Br2 Cu O6'
_chemical_formula_weight         435.60

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      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                   5.5714(17)
_cell_length_b                   6.978(2)
_cell_length_c                   10.303(3)
_cell_angle_alpha                103.643(3)
_cell_angle_beta                 101.225(3)
_cell_angle_gamma                101.936(5)
_cell_volume                     368.2(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1708
_cell_measurement_theta_min      3.9011
_cell_measurement_theta_max      29.9947

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.965
_exptl_crystal_F_000             215
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.238
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.109
_exptl_absorpt_coefficient_mu    6.921
_shelx_estimated_absorpt_T_min   0.290
_shelx_estimated_absorpt_T_max   0.519
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.3196
_exptl_absorpt_correction_T_max  0.5237
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_detector       CCD
_diffrn_measurement_device_type  'Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4709
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.867
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             1662
_reflns_number_gt                1613
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0282P)²+0.1651P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1662
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0224
_refine_ls_wR_factor_ref         0.0576
_refine_ls_wR_factor_gt          0.0566
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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
Cu1 Cu 0.5000 0.5000 0.5000 0.01886(10) Uani 1 2 d S . P . .
Br1 Br 0.74450(3) 0.50855(3) 0.72381(2) 0.02251(9) Uani 1 1 d . . . . .
O1 O 0.1132(3) 0.2015(2) 0.49767(14) 0.0200(3) Uani 1 1 d . . . . .
O2 O 0.3368(3) 0.6937(2) 0.58901(18) 0.0265(3) Uani 1 1 d . . . . .
O3 O 0.4208(3) 0.8941(3) 0.85809(16) 0.0327(4) Uani 1 1 d . . . . .
C1 C 0.0879(4) 0.0238(3) 0.3852(2) 0.0218(4) Uani 1 1 d . . . . .
C2 C 0.1371(4) 0.1457(3) 0.6243(2) 0.0210(4) Uani 1 1 d . . . . .
C3 C 0.3963(5) 0.7892(4) 0.9610(2) 0.0343(5) Uani 1 1 d . . . . .
C4 C 0.6354(5) 1.0699(4) 0.9130(2) 0.0320(5) Uani 1 1 d . . . . .
H1 H 0.247(5) -0.030(4) 0.401(3) 0.031(7) Uiso 1 1 d . . . . .
H2 H 0.060(5) 0.064(4) 0.307(3) 0.026(6) Uiso 1 1 d . . . . .
H3 H 0.143(5) 0.262(4) 0.692(3) 0.025(6) Uiso 1 1 d . . . . .
H4 H 0.286(5) 0.106(4) 0.641(3) 0.021(6) Uiso 1 1 d . . . . .
H5 H 0.250(6) 0.673(5) 0.921(3) 0.042(8) Uiso 1 1 d . . . . .
H6 H 0.549(5) 0.740(4) 0.984(3) 0.032(7) Uiso 1 1 d . . . . .
H7 H 0.797(6) 1.028(5) 0.933(3) 0.049(9) Uiso 1 1 d . . . . .
H8 H 0.641(5) 1.140(4) 0.842(3) 0.036(7) Uiso 1 1 d . . . . .
H9 H 0.207(7) 0.691(5) 0.559(4) 0.048(10) Uiso 1 1 d . . . . .
H10 H 0.367(6) 0.729(5) 0.669(4) 0.045(9) Uiso 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
Cu1 0.02140(18) 0.01931(18) 0.01606(19) 0.00337(13) 0.00369(14) 0.00883(13)
Br1 0.02420(13) 0.02333(13) 0.01898(13) 0.00605(8) 0.00227(9) 0.00722(8)
O1 0.0233(7) 0.0163(6) 0.0194(7) 0.0045(5) 0.0048(6) 0.0042(5)
O2 0.0265(8) 0.0327(8) 0.0169(8) -0.0003(6) -0.0008(6) 0.0155(7)
O3 0.0415(9) 0.0341(9) 0.0167(8) 0.0009(6) 0.0019(7) 0.0100(7)
C1 0.0264(10) 0.0197(9) 0.0196(10) 0.0041(8) 0.0080(8) 0.0066(8)
C2 0.0236(9) 0.0194(9) 0.0181(10) 0.0040(7) 0.0030(8) 0.0057(7)
C3 0.0429(13) 0.0306(12) 0.0224(12) 0.0029(9) 0.0012(10) 0.0067(10)
C4 0.0308(11) 0.0429(13) 0.0227(11) 0.0096(10) 0.0058(9) 0.0113(10)

_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
Cu1 O2 1.9347(16) 2_666 ?
Cu1 O2 1.9348(16) . ?
Cu1 Br1 2.4198(6) . ?
Cu1 Br1 2.4198(6) 2_666 ?
O1 C2 1.437(2) . ?
O1 C1 1.444(2) . ?
O2 H9 0.73(4) . ?
O2 H10 0.77(4) . ?
O3 C4 1.434(3) . ?
O3 C3 1.435(3) . ?
C1 C2 1.504(3) 2_556 ?
C1 H1 1.03(3) . ?
C1 H2 0.91(3) . ?
C2 C1 1.504(3) 2_556 ?
C2 H3 0.93(3) . ?
C2 H4 0.92(3) . ?
C3 C4 1.498(3) 2_677 ?
C3 H5 0.96(3) . ?
C3 H6 0.99(3) . ?
C4 C3 1.498(3) 2_677 ?
C4 H7 1.00(3) . ?
C4 H8 0.97(3) . ?

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
O2 Cu1 O2 180.0 2_666 . ?
O2 Cu1 Br1 90.05(6) 2_666 . ?
O2 Cu1 Br1 89.95(6) . . ?
O2 Cu1 Br1 89.95(6) 2_666 2_666 ?
O2 Cu1 Br1 90.05(6) . 2_666 ?
Br1 Cu1 Br1 180.0 . 2_666 ?
C2 O1 C1 109.23(15) . . ?
Cu1 O2 H9 121(3) . . ?
Cu1 O2 H10 119(2) . . ?
H9 O2 H10 110(4) . . ?
C4 O3 C3 109.50(18) . . ?
O1 C1 C2 110.59(16) . 2_556 ?
O1 C1 H1 110.4(15) . . ?
C2 C1 H1 107.7(15) 2_556 . ?
O1 C1 H2 105.6(17) . . ?
C2 C1 H2 108.8(16) 2_556 . ?
H1 C1 H2 114(2) . . ?
O1 C2 C1 110.96(17) . 2_556 ?
O1 C2 H3 106.1(17) . . ?
C1 C2 H3 109.6(16) 2_556 . ?
O1 C2 H4 107.4(16) . . ?
C1 C2 H4 111.1(16) 2_556 . ?
H3 C2 H4 112(2) . . ?
O3 C3 C4 109.9(2) . 2_677 ?
O3 C3 H5 107.0(18) . . ?
C4 C3 H5 111.2(18) 2_677 . ?
O3 C3 H6 109.0(17) . . ?
C4 C3 H6 110.6(17) 2_677 . ?
H5 C3 H6 109(2) . . ?
O3 C4 C3 110.2(2) . 2_677 ?
O3 C4 H7 110.9(19) . . ?
C3 C4 H7 111.4(19) 2_677 . ?
O3 C4 H8 107.1(17) . . ?
C3 C4 H8 109.1(17) 2_677 . ?
H7 C4 H8 108(3) . . ?

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
O2 H9 O1 0.73(4) 2.10(4) 2.795(2) 159(4) 2_566
O2 H10 O3 0.77(4) 1.95(4) 2.694(2) 162(3) .
C1 H2 Br1 0.91(3) 3.07(3) 3.696(2) 128(2) 2_666
C2 H3 Br1 0.93(3) 3.10(3) 3.766(2) 130(2) 1_455
C4 H8 Br1 0.97(3) 3.10(3) 4.005(3) 157(2) 1_565

_refine_diff_density_max         0.534
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.087

_shelx_res_file                  
;

    1.res created by SHELXL-2014/7

TITL 1 in P-1
CELL 0.71073   5.5714   6.9782  10.3031 103.643 101.225 101.936
ZERR    1.00   0.0017   0.0022   0.0032   0.003   0.003   0.005
LATT  1
SFAC C H O CU BR
UNIT 8 20 6 1 2
OMIT -1   5   5
OMIT 0   3   8
OMIT 1  -6  12
OMIT  -2   3  12
OMIT -2  -3  13
OMIT 0  -4  11
SHEL 6 0.77
TEMP -100
SIZE 0.238 0.144 0.109
L.S. 14
BOND $H
EQIV $1 -x,1-y,1-z
HTAB O2 O1_$1
HTAB O2 O3
EQIV $2 -x+1, -y+1, -z+1
HTAB C1 Br1_$2
EQIV $3 x-1, y, z
HTAB C2 Br1_$3
EQIV $4 x, y+1, z
HTAB C4 Br1_$4
ACTA
FMAP 2
PLAN 20
WGHT    0.028200    0.165100
FVAR       1.15896
CU1   4    0.500000    0.500000    0.500000    10.50000    0.02140    0.01931 =
         0.01606    0.00337    0.00369    0.00883
BR1   5    0.744501    0.508551    0.723814    11.00000    0.02420    0.02333 =
         0.01898    0.00605    0.00227    0.00722
O1    3    0.113192    0.201504    0.497668    11.00000    0.02326    0.01627 =
         0.01940    0.00451    0.00477    0.00425
O2    3    0.336830    0.693735    0.589011    11.00000    0.02654    0.03271 =
         0.01691   -0.00029   -0.00081    0.01550
O3    3    0.420755    0.894086    0.858093    11.00000    0.04150    0.03410 =
         0.01674    0.00089    0.00186    0.01000
C1    1    0.087859    0.023807    0.385223    11.00000    0.02640    0.01967 =
         0.01964    0.00409    0.00803    0.00661
C2    1    0.137073    0.145687    0.624293    11.00000    0.02361    0.01938 =
         0.01812    0.00399    0.00303    0.00570
C3    1    0.396313    0.789168    0.960983    11.00000    0.04288    0.03056 =
         0.02242    0.00294    0.00121    0.00672
C4    1    0.635351    1.069913    0.912959    11.00000    0.03079    0.04285 =
         0.02273    0.00964    0.00582    0.01127
H1    2    0.246650   -0.029710    0.400767    11.00000    0.03118
H2    2    0.059555    0.064492    0.307429    11.00000    0.02574
H3    2    0.143277    0.261981    0.692156    11.00000    0.02548
H4    2    0.285603    0.106117    0.640571    11.00000    0.02121
H5    2    0.250371    0.673198    0.920555    11.00000    0.04240
H6    2    0.548883    0.740249    0.984032    11.00000    0.03228
H7    2    0.796807    1.028218    0.933153    11.00000    0.04923
H8    2    0.641217    1.139681    0.842188    11.00000    0.03606
H9    2    0.206843    0.691315    0.558727    11.00000    0.04770
H10   2    0.366564    0.728914    0.668841    11.00000    0.04513
HKLF 4

REM  1 in P-1
REM R1 =  0.0224 for    1613 Fo > 4sig(Fo)  and  0.0238 for all    1662 data
REM    119 parameters refined using      0 restraints

END

WGHT      0.0282      0.1651

REM Highest difference peak  0.534,  deepest hole -0.410,  1-sigma level  0.087
Q1    1  -0.0179  0.5052  0.9469  11.00000  0.05    0.53
Q2    1   0.8992  0.4875  0.7394  11.00000  0.05    0.36
Q3    1  -0.0160 -0.0582  0.3825  11.00000  0.05    0.33
Q4    1  -0.1236 -0.0157  0.1747  11.00000  0.05    0.32
Q5    1   0.8315  0.5022  0.6663  11.00000  0.05    0.32
Q6    1   0.2267  0.6240  0.4359  11.00000  0.05    0.31
Q7    1   0.4587  0.2403  0.5755  11.00000  0.05    0.30
Q8    1   0.6713  0.5104  0.7817  11.00000  0.05    0.30
Q9    1   0.5822  0.5428  0.6868  11.00000  0.05    0.30
Q10   1   0.3353  0.5469  0.4827  11.00000  0.05    0.30
Q11   1   0.3447 -0.2219  0.3887  11.00000  0.05    0.29
Q12   1   0.7224  1.2310  0.7979  11.00000  0.05    0.29
Q13   1   0.8087  0.6338  0.7308  11.00000  0.05    0.28
Q14   1   0.0292  0.4230  0.7904  11.00000  0.05    0.28
Q15   1   0.1862  0.0121  0.3475  11.00000  0.05    0.27
Q16   1   0.4252  0.3551  0.4796  11.00000  0.05    0.27
Q17   1   0.6749  0.3785  0.7088  11.00000  0.05    0.26
Q18   1   0.6036  0.7664  0.9442  11.00000  0.05    0.25
Q19   1   0.3953  0.8441  0.9114  11.00000  0.05    0.25
Q20   1   0.1092  0.0728  0.4417  11.00000  0.05    0.25
;
_shelx_res_checksum              51925
####################################################################### 
# 
# 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_320
_audit_block_doi                 10.5517/cc1jbsg3
_database_code_depnum_ccdc_archive 'CCDC 1410545'
_audit_update_record             
;
2015-07-04 deposited with the CCDC.
2015-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H16 Br6 Cu3 O4'
_chemical_formula_weight         846.29

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'
Cu Cu 0.3201 1.2651 '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                   7.919(5)
_cell_length_b                   12.382(7)
_cell_length_c                   9.560(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.177(8)
_cell_angle_gamma                90
_cell_volume                     895.6(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1433
_cell_measurement_theta_min      2.2285
_cell_measurement_theta_max      27.4659

_exptl_crystal_description       block
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.138
_exptl_crystal_F_000             786
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    16.922
_shelx_estimated_absorpt_T_min   0.125
_shelx_estimated_absorpt_T_max   0.551
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.0868
_exptl_absorpt_correction_T_max  0.3719
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_detector       CCD
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       dtprofit.ref
_diffrn_reflns_number            3604
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.230
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             1078
_reflns_number_gt                1032
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0422P)²+6.0425P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1078
_refine_ls_number_parameters     55
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.0962
_refine_ls_wR_factor_gt          0.0950
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_restrained_S_all      1.151
_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
Cu1 Cu 0.09299(11) 0.0000 0.69170(8) 0.0203(2) Uani 1 2 d S T P . .
Cu2 Cu 0.0000 0.0000 1.0000 0.0209(3) Uani 1 4 d S T P . .
Br1 Br 0.0000 0.13529(5) 0.5000 0.0215(2) Uani 1 2 d S T P . .
Br2 Br 0.13545(6) 0.13495(4) 0.88362(5) 0.02077(18) Uani 1 1 d . . . . .
O1 O 0.3887(6) 0.0000 0.6853(6) 0.0242(10) Uani 1 2 d S T P . .
C1 C 0.4916(7) 0.0952(4) 0.7414(6) 0.0228(10) Uani 1 1 d . . . . .
H1A H 0.5175 0.0976 0.8492 0.027 Uiso 1 1 calc R U . . .
H1B H 0.4224 0.1604 0.7002 0.027 Uiso 1 1 calc R U . . .
C2 C 0.6619(7) 0.0955(4) 0.7027(6) 0.0248(11) Uani 1 1 d . . . . .
H2A H 0.6366 0.0974 0.5949 0.030 Uiso 1 1 calc R U . . .
H2B H 0.7311 0.1607 0.7438 0.030 Uiso 1 1 calc R U . . .
O2 O 0.7635(6) 0.0000 0.7604(6) 0.0231(10) Uani 1 2 d S T P . .

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
Cu1 0.0237(4) 0.0200(4) 0.0171(4) 0.000 0.0058(3) 0.000
Cu2 0.0227(6) 0.0196(6) 0.0234(6) 0.000 0.0116(5) 0.000
Br1 0.0258(4) 0.0196(4) 0.0182(4) 0.000 0.0053(3) 0.000
Br2 0.0226(3) 0.0209(3) 0.0199(3) -0.00151(16) 0.0080(2) -0.00308(16)
O1 0.015(2) 0.025(2) 0.031(3) 0.000 0.005(2) 0.000
C1 0.021(2) 0.020(2) 0.028(2) -0.0006(19) 0.008(2) 0.0010(19)
C2 0.019(2) 0.023(2) 0.033(3) 0.005(2) 0.008(2) 0.002(2)
O2 0.018(2) 0.020(2) 0.028(3) 0.000 0.002(2) 0.000

_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
Cu1 O1 2.361(5) . ?
Cu1 Br2 2.4304(13) . ?
Cu1 Br2 2.4304(13) 6 ?
Cu1 Br1 2.4311(13) 5_556 ?
Cu1 Br1 2.4311(13) . ?
Cu2 Br2 2.4260(10) 6 ?
Cu2 Br2 2.4260(10) . ?
Cu2 Br2 2.4260(10) 2_557 ?
Cu2 Br2 2.4260(10) 5_557 ?
Br1 Cu1 2.4311(13) 2_556 ?
O1 C1 1.443(6) . ?
O1 C1 1.443(6) 6 ?
C1 C2 1.500(7) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 O2 1.445(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
O2 C2 1.445(6) 6 ?

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
O1 Cu1 Br2 95.88(10) . . ?
O1 Cu1 Br2 95.88(10) . 6 ?
Br2 Cu1 Br2 86.87(6) . 6 ?
O1 Cu1 Br1 93.57(10) . 5_556 ?
Br2 Cu1 Br1 170.54(4) . 5_556 ?
Br2 Cu1 Br1 92.23(5) 6 5_556 ?
O1 Cu1 Br1 93.57(10) . . ?
Br2 Cu1 Br1 92.23(5) . . ?
Br2 Cu1 Br1 170.54(4) 6 . ?
Br1 Cu1 Br1 87.12(6) 5_556 . ?
Br2 Cu2 Br2 87.07(5) 6 . ?
Br2 Cu2 Br2 179.999(15) 6 2_557 ?
Br2 Cu2 Br2 92.93(5) . 2_557 ?
Br2 Cu2 Br2 92.93(5) 6 5_557 ?
Br2 Cu2 Br2 180.0 . 5_557 ?
Br2 Cu2 Br2 87.07(5) 2_557 5_557 ?
Cu1 Br1 Cu1 92.88(6) 2_556 . ?
Cu2 Br2 Cu1 83.76(5) . . ?
C1 O1 C1 109.5(5) . 6 ?
C1 O1 Cu1 116.5(3) . . ?
C1 O1 Cu1 116.5(3) 6 . ?
O1 C1 C2 111.1(4) . . ?
O1 C1 H1A 109.4 . . ?
C2 C1 H1A 109.4 . . ?
O1 C1 H1B 109.4 . . ?
C2 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
O2 C2 C1 110.1(4) . . ?
O2 C2 H2A 109.6 . . ?
C1 C2 H2A 109.6 . . ?
O2 C2 H2B 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.2 . . ?
C2 O2 C2 109.8(5) . 6 ?

_refine_diff_density_max         1.097
_refine_diff_density_min         -0.955
_refine_diff_density_rms         0.227

_shelx_res_file                  
;

    1.res created by SHELXL-2014/7

TITL 1 in C2/m
CELL 0.71073   7.9189  12.3822   9.5597  90.000 107.177  90.000
ZERR    2.00   0.0051   0.0073   0.0063   0.000   0.008   0.000
LATT  7
SYMM -X, Y, -Z
SFAC C H O Br CU
UNIT 16 32 8 12 6
OMIT 4 0 4
TEMP -100
SIZE 0.21 0.10 0.04
L.S. 6
BOND $H
FMAP 2
PLAN 20
ACTA
HTAB
EQIV $1 -x,y,1-z
EQIV $2 -x,-y,1-z
EQIV $3 x,-y,z
MPLA 6 Br1 Br1_$2 Br2 Br2_$2 Br2_$3 Cu1 Cu1_$1
EQIV $4 x,y,-1+z
EQIV $5 x,-y,-1+z
MPLA 4 Br2_$1 Br2_$2 Br2_$4 Br2_$5 Cu2_$4
EQIV $6 -1+x,y,z
RTAB X..Y Cu1 O2_$6
RTAB XYZ Cu1 Br1 Cu1_$1
RTAB XYZ Cu1 Br2 Cu2
EQIV $7 1+x,y,z
RTAB X..Y Cu1 Cu2
RTAB X..Y Cu1 Cu1_$1
RTAB X..Y Cu1_$1 Cu2_$4
RTAB X..Y Cu1 Cu2_$7
RTAB X..Y Cu1_$7 Cu2_$7
EQIV $8 1-x,y,2-z
RTAB X..Y Cu2 Cu1_$8
RTAB X..Y Cu2_$7 Cu1_$8
EQIV $9 1-x,y,1-z
RTAB X..Y Cu2_$4 Cu1_$9
RTAB X..Y Cu1_$7 Cu1_$9
EQIV $10 0.5-x,0.5-y,2-z
RTAB X..Y Br2 Br2_$10
WGHT    0.042200    6.042500
FVAR       2.60631
CU1   5    0.092986    0.000000    0.691702    10.50000    0.02374    0.01999 =
         0.01710    0.00000    0.00584    0.00000
CU2   5    0.000000    0.000000    1.000000    10.25000    0.02266    0.01960 =
         0.02340    0.00000    0.01159    0.00000
BR1   4    0.000000    0.135294    0.500000    10.50000    0.02583    0.01964 =
         0.01823    0.00000    0.00525    0.00000
BR2   4    0.135454    0.134949    0.883617    11.00000    0.02261    0.02095 =
         0.01988   -0.00151    0.00802   -0.00308
O1    3    0.388697    0.000000    0.685268    10.50000    0.01493    0.02491 =
         0.03134    0.00000    0.00456    0.00000
C1    1    0.491629    0.095189    0.741449    11.00000    0.02133    0.02028 =
         0.02756   -0.00065    0.00847    0.00097
AFIX  23
H1A   2    0.517464    0.097608    0.849242    11.00000   -1.20000
H1B   2    0.422396    0.160397    0.700246    11.00000   -1.20000
AFIX   0
C2    1    0.661939    0.095472    0.702699    11.00000    0.01880    0.02319 =
         0.03292    0.00520    0.00826    0.00186
AFIX  23
H2A   2    0.636578    0.097401    0.594929    11.00000   -1.20000
H2B   2    0.731078    0.160740    0.743778    11.00000   -1.20000
AFIX   0
O2    3    0.763542    0.000000    0.760412    10.50000    0.01794    0.01995 =
         0.02833    0.00000    0.00205    0.00000
HKLF 4

REM  1 in C2/m
REM R1 =  0.0393 for    1032 Fo > 4sig(Fo)  and  0.0413 for all    1078 data
REM     55 parameters refined using      0 restraints

END

WGHT      0.0422      6.0426

REM Instructions for potential hydrogen bonds
HTAB C2 Br2_$7
EQIV $11 x+1/2, -y+1/2, z
HTAB C2 Br2_$11

REM Highest difference peak  1.097,  deepest hole -0.955,  1-sigma level  0.227
Q1    1   0.1332  0.1346  0.9538  11.00000  0.05    1.10
Q2    1   0.0404  0.0668  0.6016  11.00000  0.05    1.02
Q3    1   0.0176  0.0000  0.8438  10.50000  0.05    0.91
Q4    1   0.0039  0.1391  0.5623  11.00000  0.05    0.91
Q5    1   0.9262 -0.0605  0.8054  11.00000  0.05    0.91
Q6    1   0.0932  0.0000  0.7648  10.50000  0.05    0.89
Q7    1   0.0480  0.0663  0.9137  11.00000  0.05    0.82
Q8    1   0.4414  0.1758  0.8148  11.00000  0.05    0.80
Q9    1   0.0997  0.0715  0.7843  11.00000  0.05    0.77
Q10   1   0.0902  0.2068  0.7838  11.00000  0.05    0.71
Q11   1   0.0589  0.2041  0.8948  11.00000  0.05    0.70
Q12   1   0.0269  0.1367  0.3374  11.00000  0.05    0.70
Q13   1   0.8296  0.0000  0.7597  10.50000  0.05    0.68
Q14   1   0.0493  0.2068  0.5997  11.00000  0.05    0.68
Q15   1   0.0000  0.0675  0.5000  10.50000  0.05    0.67
Q16   1   0.1216  0.1294  1.0620  11.00000  0.05    0.66
Q17   1   0.0000  0.0785  1.0000  10.50000  0.05    0.66
Q18   1   0.0807  0.0000  0.6538  10.50000  0.05    0.63
Q19   1   0.1606  0.0674  0.8781  11.00000  0.05    0.62
Q20   1   0.1648  0.1404  0.7238  11.00000  0.05    0.61
;
_shelx_res_checksum              60368
