# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1020489'
_audit_update_record             
;
2014-08-21 deposited with the CCDC.
2015-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H16 Br7 Cu N4 O2'
_chemical_formula_sum            'C26 H16 Br7 Cu N4 O2'
_chemical_formula_weight         1039.34

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_HALL  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.402(5)
_cell_length_b                   21.994(5)
_cell_length_c                   19.692(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 100.110(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     3156(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4514
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      22.06

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            BLACK
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1960
_exptl_absorpt_coefficient_mu    9.586
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.2165
_exptl_absorpt_correction_T_max  0.2381
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean '\f and \w scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22266
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5555
_reflns_number_gt                3808
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0803P)²+10.0506P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5555
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1558
_refine_ls_wR_factor_gt          0.1388
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br7 Br 1.08655(13) -0.06050(4) 0.61361(5) 0.0565(3) Uani 1 1 d . . .
Br5 Br 0.58382(14) 0.91427(5) 0.43702(5) 0.0596(3) Uani 1 1 d . . .
Br4 Br 0.85199(13) 0.71966(4) 0.61733(6) 0.0586(3) Uani 1 1 d . . .
Br6 Br 0.91095(13) 0.07583(5) 0.83947(5) 0.0608(3) Uani 1 1 d . . .
Cu1 Cu 0.56121(16) 0.82185(4) 0.80486(5) 0.0487(3) Uani 1 1 d . . .
Br3 Br 0.23182(15) 0.81390(5) 0.77008(5) 0.0682(3) Uani 1 1 d . . .
Br1 Br 0.6213(2) 0.71761(5) 0.80059(6) 0.0990(5) Uani 1 1 d . . .
Br2 Br 0.80785(19) 0.84603(6) 0.89486(8) 0.0979(5) Uani 1 1 d . . .
O2 O 0.8299(8) 0.1562(2) 0.5206(3) 0.0461(14) Uani 1 1 d . . .
O1 O 0.5385(7) 0.9824(2) 0.6906(3) 0.0429(13) Uani 1 1 d . . .
N3 N 0.8159(10) 0.2220(3) 0.6027(4) 0.0501(18) Uani 1 1 d . . .
C20 C 0.8545(11) 0.1651(4) 0.5884(4) 0.0423(19) Uani 1 1 d . . .
C13 C 0.7105(10) 0.8301(4) 0.6568(4) 0.0418(19) Uani 1 1 d . . .
H13 H 0.7384 0.8136 0.7009 0.050 Uiso 1 1 calc R . .
C7 C 0.5793(10) 0.9222(3) 0.7035(4) 0.0370(18) Uani 1 1 d . . .
C12 C 0.7490(11) 0.7990(4) 0.6017(4) 0.0421(19) Uani 1 1 d . . .
N1 N 0.5595(9) 0.9055(3) 0.7654(3) 0.0409(16) Uani 1 1 d . . .
C23 C 1.0022(11) 0.0118(4) 0.6501(5) 0.045(2) Uani 1 1 d . . .
C8 C 0.6281(10) 0.8876(4) 0.6467(4) 0.0399(19) Uani 1 1 d . . .
C26 C 0.8941(10) 0.1194(4) 0.7037(4) 0.046(2) Uani 1 1 d . . .
H26 H 0.8608 0.1559 0.7219 0.055 Uiso 1 1 calc R . .
C11 C 0.7116(11) 0.8198(4) 0.5343(4) 0.043(2) Uani 1 1 d . . .
C22 C 0.9616(11) 0.0607(4) 0.6083(4) 0.044(2) Uani 1 1 d . . .
H22 H 0.9709 0.0578 0.5620 0.052 Uiso 1 1 calc R . .
C14 C 0.7608(12) 0.2535(4) 0.5402(5) 0.049(2) Uani 1 1 d . . .
N2 N 0.7525(11) 0.7880(4) 0.4796(4) 0.060(2) Uani 1 1 d . . .
H2A H 0.8044 0.7530 0.4860 0.072 Uiso 1 1 calc R . .
H2B H 0.7265 0.8029 0.4387 0.072 Uiso 1 1 calc R . .
C17 C 0.6682(13) 0.2829(5) 0.4041(5) 0.066(3) Uani 1 1 d . . .
H17 H 0.6334 0.2942 0.3581 0.079 Uiso 1 1 calc R . .
C19 C 0.7695(11) 0.2122(4) 0.4893(4) 0.043(2) Uani 1 1 d . . .
C6 C 0.4901(10) 1.0039(4) 0.7500(4) 0.0418(19) Uani 1 1 d . . .
C5 C 0.4378(12) 1.0619(4) 0.7626(5) 0.052(2) Uani 1 1 d . . .
H5 H 0.4314 1.0927 0.7299 0.062 Uiso 1 1 calc R . .
C10 C 0.6336(11) 0.8787(4) 0.5266(4) 0.0421(19) Uani 1 1 d . . .
C24 C 0.9855(10) 0.0128(4) 0.7214(4) 0.0427(19) Uani 1 1 d . . .
C1 C 0.5049(11) 0.9578(4) 0.7967(4) 0.0419(19) Uani 1 1 d . . .
N4 N 1.0146(10) -0.0359(4) 0.7611(4) 0.058(2) Uani 1 1 d . . .
H4A H 1.0011 -0.0339 0.8036 0.070 Uiso 1 1 calc R . .
H4B H 1.0470 -0.0695 0.7445 0.070 Uiso 1 1 calc R . .
C21 C 0.9057(11) 0.1154(4) 0.6342(4) 0.0412(19) Uani 1 1 d . . .
C9 C 0.5924(11) 0.9108(4) 0.5802(4) 0.0420(19) Uani 1 1 d . . .
H9 H 0.5394 0.9491 0.5725 0.050 Uiso 1 1 calc R . .
C25 C 0.9320(11) 0.0696(4) 0.7450(4) 0.0426(19) Uani 1 1 d . . .
C18 C 0.7255(12) 0.2244(4) 0.4204(5) 0.054(2) Uani 1 1 d . . .
H18 H 0.7338 0.1952 0.3868 0.065 Uiso 1 1 calc R . .
C4 C 0.3956(12) 1.0715(4) 0.8266(5) 0.057(2) Uani 1 1 d . . .
H4 H 0.3547 1.1097 0.8373 0.068 Uiso 1 1 calc R . .
C2 C 0.4660(13) 0.9666(4) 0.8624(5) 0.057(2) Uani 1 1 d . . .
H2 H 0.4750 0.9357 0.8950 0.069 Uiso 1 1 calc R . .
C16 C 0.6620(14) 0.3249(5) 0.4560(6) 0.067(3) Uani 1 1 d . . .
H16 H 0.6259 0.3644 0.4435 0.080 Uiso 1 1 calc R . .
C15 C 0.7061(14) 0.3114(5) 0.5245(6) 0.068(3) Uani 1 1 d . . .
H15 H 0.6991 0.3403 0.5585 0.082 Uiso 1 1 calc R . .
C3 C 0.4119(13) 1.0260(5) 0.8758(5) 0.062(3) Uani 1 1 d . . .
H3 H 0.3862 1.0350 0.9193 0.075 Uiso 1 1 calc R . .


_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
Br7 C23 1.896(8) . ?
Br5 C10 1.906(8) . ?
Br4 C12 1.907(8) . ?
Br6 C25 1.898(8) . ?
Cu1 N1 1.997(6) . ?
Cu1 Br1 2.3397(15) . ?
Cu1 Br2 2.3707(19) . ?
Cu1 Br3 2.420(2) . ?
O2 C20 1.328(10) . ?
O2 C19 1.416(10) . ?
O1 C6 1.366(10) . ?
O1 C7 1.372(9) . ?
N3 C20 1.326(10) . ?
N3 C14 1.409(11) . ?
C20 C21 1.426(11) . ?
C13 C12 1.355(11) . ?
C13 C8 1.402(11) . ?
C13 H13 0.9300 . ?
C7 N1 1.306(10) . ?
C7 C8 1.451(11) . ?
C12 C11 1.386(12) . ?
N1 C1 1.397(10) . ?
C23 C22 1.355(11) . ?
C23 C24 1.430(12) . ?
C8 C9 1.387(11) . ?
C26 C25 1.365(12) . ?
C26 C21 1.388(11) . ?
C26 H26 0.9300 . ?
C11 N2 1.361(11) . ?
C11 C10 1.416(12) . ?
C22 C21 1.397(11) . ?
C22 H22 0.9300 . ?
C14 C15 1.356(12) . ?
C14 C19 1.364(12) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C17 C18 1.375(14) . ?
C17 C16 1.385(15) . ?
C17 H17 0.9300 . ?
C19 C18 1.366(12) . ?
C6 C1 1.359(11) . ?
C6 C5 1.369(11) . ?
C5 C4 1.366(14) . ?
C5 H5 0.9300 . ?
C10 C9 1.348(11) . ?
C24 N4 1.322(11) . ?
C24 C25 1.413(12) . ?
C1 C2 1.389(12) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
C9 H9 0.9300 . ?
C18 H18 0.9300 . ?
C4 C3 1.384(14) . ?
C4 H4 0.9300 . ?
C2 C3 1.404(13) . ?
C2 H2 0.9300 . ?
C16 C15 1.364(14) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?
C3 H3 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
N1 Cu1 Br1 151.3(2) . . ?
N1 Cu1 Br2 92.05(19) . . ?
Br1 Cu1 Br2 96.91(6) . . ?
N1 Cu1 Br3 91.1(2) . . ?
Br1 Cu1 Br3 96.17(7) . . ?
Br2 Cu1 Br3 146.41(7) . . ?
C20 O2 C19 106.7(6) . . ?
C6 O1 C7 104.9(6) . . ?
C20 N3 C14 108.5(7) . . ?
N3 C20 O2 110.9(7) . . ?
N3 C20 C21 129.2(8) . . ?
O2 C20 C21 119.8(7) . . ?
C12 C13 C8 119.3(8) . . ?
C12 C13 H13 120.4 . . ?
C8 C13 H13 120.4 . . ?
N1 C7 O1 112.8(7) . . ?
N1 C7 C8 131.0(7) . . ?
O1 C7 C8 116.2(7) . . ?
C13 C12 C11 124.4(8) . . ?
C13 C12 Br4 117.9(6) . . ?
C11 C12 Br4 117.7(6) . . ?
C7 N1 C1 105.6(6) . . ?
C7 N1 Cu1 129.0(5) . . ?
C1 N1 Cu1 124.7(5) . . ?
C22 C23 C24 122.4(8) . . ?
C22 C23 Br7 119.2(7) . . ?
C24 C23 Br7 118.4(6) . . ?
C9 C8 C13 118.2(8) . . ?
C9 C8 C7 120.1(7) . . ?
C13 C8 C7 121.6(7) . . ?
C25 C26 C21 119.6(8) . . ?
C25 C26 H26 120.2 . . ?
C21 C26 H26 120.2 . . ?
N2 C11 C12 123.5(8) . . ?
N2 C11 C10 122.0(8) . . ?
C12 C11 C10 114.4(7) . . ?
C23 C22 C21 120.7(8) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C15 C14 C19 120.6(9) . . ?
C15 C14 N3 133.7(9) . . ?
C19 C14 N3 105.8(7) . . ?
C11 N2 H2A 120.0 . . ?
C11 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C18 C17 C16 120.1(9) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C18 C19 C14 124.5(8) . . ?
C18 C19 O2 127.3(8) . . ?
C14 C19 O2 108.1(7) . . ?
C1 C6 C5 124.4(9) . . ?
C1 C6 O1 108.6(7) . . ?
C5 C6 O1 127.0(8) . . ?
C6 C5 C4 115.3(9) . . ?
C6 C5 H5 122.3 . . ?
C4 C5 H5 122.3 . . ?
C9 C10 C11 122.7(8) . . ?
C9 C10 Br5 118.4(6) . . ?
C11 C10 Br5 118.9(6) . . ?
N4 C24 C25 123.1(8) . . ?
N4 C24 C23 122.4(8) . . ?
C25 C24 C23 114.5(7) . . ?
C6 C1 C2 121.4(8) . . ?
C6 C1 N1 108.1(7) . . ?
C2 C1 N1 130.5(8) . . ?
C24 N4 H4A 120.0 . . ?
C24 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C26 C21 C22 119.2(8) . . ?
C26 C21 C20 121.3(8) . . ?
C22 C21 C20 119.5(8) . . ?
C10 C9 C8 120.9(8) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C26 C25 C24 123.6(8) . . ?
C26 C25 Br6 118.9(7) . . ?
C24 C25 Br6 117.6(6) . . ?
C19 C18 C17 115.2(9) . . ?
C19 C18 H18 122.4 . . ?
C17 C18 H18 122.4 . . ?
C5 C4 C3 121.9(9) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C1 C2 C3 114.7(9) . . ?
C1 C2 H2 122.7 . . ?
C3 C2 H2 122.7 . . ?
C15 C16 C17 123.5(10) . . ?
C15 C16 H16 118.2 . . ?
C17 C16 H16 118.2 . . ?
C14 C15 C16 116.1(10) . . ?
C14 C15 H15 121.9 . . ?
C16 C15 H15 121.9 . . ?
C4 C3 C2 122.2(9) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         2.273
_refine_diff_density_min         -0.841
_refine_diff_density_rms         0.138
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1020490'
_audit_update_record             
;
2014-08-21 deposited with the CCDC.
2015-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H8 Br3 Cu N2 O'
_chemical_formula_sum            'C13 H8 Br3 Cu N2 O'
_chemical_formula_weight         511.48

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P n'
_symmetry_space_group_name_HALL  'P -2yac'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   4.043(5)
_cell_length_b                   14.545(5)
_cell_length_c                   12.082(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 95.877(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     706.8(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2597
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      26.50

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             484
_exptl_absorpt_coefficient_mu    10.019
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2065
_exptl_absorpt_correction_T_max  0.2274
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4840
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         24.98
_reflns_number_total             2349
_reflns_number_gt                2192
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0178P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.022(11)
_refine_ls_number_reflns         2349
_refine_ls_number_parameters     178
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0232
_refine_ls_wR_factor_ref         0.0490
_refine_ls_wR_factor_gt          0.0481
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.990
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.34133(11) 0.20900(4) 0.80182(4) 0.04735(16) Uani 1 1 d . . .
Br2 Br 1.36964(10) 0.20276(3) 0.11285(4) 0.03666(13) Uani 1 1 d . . .
Br3 Br 1.43135(13) -0.00870(3) 0.50895(5) 0.04555(15) Uani 1 1 d . . .
C1 C 0.5918(11) 0.4124(3) 0.5700(4) 0.0305(11) Uani 1 1 d . . .
C2 C 0.4328(12) 0.4571(4) 0.6519(4) 0.0380(12) Uani 1 1 d . . .
H2 H 0.4174 0.4307 0.7213 0.046 Uiso 1 1 calc R . .
C3 C 0.2969(13) 0.5440(4) 0.6240(5) 0.0456(14) Uani 1 1 d . . .
H3 H 0.1853 0.5758 0.6757 0.055 Uiso 1 1 calc R . .
C4 C 0.3265(10) 0.5834(3) 0.5201(3) 0.0490(14) Uani 1 1 d . . .
H4 H 0.2450 0.6426 0.5062 0.059 Uiso 1 1 calc R . .
C5 C 0.4715(10) 0.5382(3) 0.4376(3) 0.0416(12) Uani 1 1 d R . .
H5 H 0.4848 0.5631 0.3673 0.050 Uiso 1 1 d R . .
C6 C 0.6053(12) 0.4529(3) 0.4682(4) 0.0339(12) Uani 1 1 d . . .
C7 C 0.8571(13) 0.3199(3) 0.4710(4) 0.0286(10) Uani 1 1 d . . .
C8 C 1.0364(11) 0.2475(3) 0.4221(4) 0.0283(10) Uani 1 1 d . . .
C9 C 1.1163(11) 0.2568(3) 0.3124(4) 0.0285(10) Uani 1 1 d . . .
H9 H 1.0596 0.3105 0.2731 0.034 Uiso 1 1 calc R . .
C10 C 1.2786(10) 0.1870(3) 0.2623(3) 0.0257(10) Uani 1 1 d . . .
C11 C 1.3732(10) 0.1054(3) 0.3172(4) 0.0251(9) Uani 1 1 d . . .
C12 C 1.2953(11) 0.0992(3) 0.4292(3) 0.0271(10) Uani 1 1 d . . .
C13 C 1.1313(10) 0.1665(3) 0.4795(4) 0.0269(10) Uani 1 1 d . . .
H13 H 1.0818 0.1587 0.5524 0.032 Uiso 1 1 calc R . .
Cu1 Cu 0.81492(16) 0.25026(4) 0.70617(5) 0.04166(17) Uani 1 1 d . . .
O1 O 0.7730(8) 0.39395(19) 0.4032(3) 0.0330(7) Uani 1 1 d . . .
N2 N 1.5323(11) 0.0375(3) 0.2683(3) 0.0407(11) Uani 1 1 d . . .
H2A H 1.5789 0.0437 0.2008 0.049 Uiso 1 1 calc R . .
H2B H 1.5873 -0.0120 0.3045 0.049 Uiso 1 1 calc R . .
N1 N 0.7516(9) 0.3269(3) 0.5690(3) 0.0280(8) 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
Br1 Cu1 2.392(2) 1_455 ?
Br1 Cu1 2.411(2) . ?
Br2 C10 1.894(4) . ?
Br3 C12 1.893(4) . ?
C1 C6 1.370(6) . ?
C1 C2 1.394(6) . ?
C1 N1 1.403(6) . ?
C2 C3 1.406(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.396(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.3750 . ?
C4 H4 0.9300 . ?
C5 C6 1.388(6) . ?
C5 H5 0.9300 . ?
C6 O1 1.386(5) . ?
C7 N1 1.303(6) . ?
C7 O1 1.375(5) . ?
C7 C8 1.439(6) . ?
C8 C13 1.400(6) . ?
C8 C9 1.402(6) . ?
C9 C10 1.382(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.394(6) . ?
C11 N2 1.348(6) . ?
C11 C12 1.424(6) . ?
C12 C13 1.360(6) . ?
C13 H13 0.9300 . ?
Cu1 N1 1.992(4) . ?
Cu1 Br1 2.392(2) 1_655 ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?

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
Cu1 Br1 Cu1 114.64(7) 1_455 . ?
C6 C1 C2 120.1(4) . . ?
C6 C1 N1 108.2(4) . . ?
C2 C1 N1 131.7(5) . . ?
C1 C2 C3 116.5(5) . . ?
C1 C2 H2 121.8 . . ?
C3 C2 H2 121.8 . . ?
C4 C3 C2 121.2(5) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C5 C4 C3 122.5(3) . . ?
C5 C4 H4 118.7 . . ?
C3 C4 H4 118.7 . . ?
C4 C5 C6 114.7(2) . . ?
C4 C5 H5 123.0 . . ?
C6 C5 H5 122.3 . . ?
C1 C6 O1 108.0(4) . . ?
C1 C6 C5 124.9(4) . . ?
O1 C6 C5 127.0(4) . . ?
N1 C7 O1 113.3(4) . . ?
N1 C7 C8 131.0(4) . . ?
O1 C7 C8 115.7(4) . . ?
C13 C8 C9 118.2(4) . . ?
C13 C8 C7 122.4(4) . . ?
C9 C8 C7 119.4(4) . . ?
C10 C9 C8 120.5(4) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 122.5(4) . . ?
C9 C10 Br2 118.4(3) . . ?
C11 C10 Br2 119.1(3) . . ?
N2 C11 C10 122.3(4) . . ?
N2 C11 C12 122.2(4) . . ?
C10 C11 C12 115.5(4) . . ?
C13 C12 C11 123.0(4) . . ?
C13 C12 Br3 120.0(3) . . ?
C11 C12 Br3 117.1(3) . . ?
C12 C13 C8 120.4(4) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
N1 Cu1 Br1 125.07(11) . 1_655 ?
N1 Cu1 Br1 119.82(12) . . ?
Br1 Cu1 Br1 114.64(7) 1_655 . ?
C7 O1 C6 104.7(3) . . ?
C11 N2 H2A 120.0 . . ?
C11 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C7 N1 C1 105.7(4) . . ?
C7 N1 Cu1 133.3(3) . . ?
C1 N1 Cu1 120.6(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
C6 C1 C2 C3 -0.9(7) . . . . ?
N1 C1 C2 C3 -179.9(5) . . . . ?
C1 C2 C3 C4 -1.1(7) . . . . ?
C2 C3 C4 C5 3.8(6) . . . . ?
C3 C4 C5 C6 -4.1(3) . . . . ?
C2 C1 C6 O1 -179.5(4) . . . . ?
N1 C1 C6 O1 -0.2(5) . . . . ?
C2 C1 C6 C5 0.4(7) . . . . ?
N1 C1 C6 C5 179.6(4) . . . . ?
C4 C5 C6 C1 2.0(5) . . . . ?
C4 C5 C6 O1 -178.1(3) . . . . ?
N1 C7 C8 C13 0.0(8) . . . . ?
O1 C7 C8 C13 -178.2(4) . . . . ?
N1 C7 C8 C9 179.0(5) . . . . ?
O1 C7 C8 C9 0.8(6) . . . . ?
C13 C8 C9 C10 1.2(6) . . . . ?
C7 C8 C9 C10 -177.9(4) . . . . ?
C8 C9 C10 C11 -0.7(7) . . . . ?
C8 C9 C10 Br2 178.5(3) . . . . ?
C9 C10 C11 N2 -179.8(4) . . . . ?
Br2 C10 C11 N2 1.0(6) . . . . ?
C9 C10 C11 C12 -0.8(6) . . . . ?
Br2 C10 C11 C12 -180.0(3) . . . . ?
N2 C11 C12 C13 -179.2(4) . . . . ?
C10 C11 C12 C13 1.8(6) . . . . ?
N2 C11 C12 Br3 1.0(6) . . . . ?
C10 C11 C12 Br3 -178.0(3) . . . . ?
C11 C12 C13 C8 -1.4(7) . . . . ?
Br3 C12 C13 C8 178.5(3) . . . . ?
C9 C8 C13 C12 -0.2(6) . . . . ?
C7 C8 C13 C12 178.8(4) . . . . ?
Cu1 Br1 Cu1 N1 7.49(14) 1_455 . . . ?
Cu1 Br1 Cu1 Br1 180.0 1_455 . . 1_655 ?
N1 C7 O1 C6 1.5(5) . . . . ?
C8 C7 O1 C6 179.9(4) . . . . ?
C1 C6 O1 C7 -0.7(5) . . . . ?
C5 C6 O1 C7 179.5(4) . . . . ?
O1 C7 N1 C1 -1.6(5) . . . . ?
C8 C7 N1 C1 -179.8(5) . . . . ?
O1 C7 N1 Cu1 -174.9(3) . . . . ?
C8 C7 N1 Cu1 7.0(8) . . . . ?
C6 C1 N1 C7 1.1(5) . . . . ?
C2 C1 N1 C7 -179.8(5) . . . . ?
C6 C1 N1 Cu1 175.4(3) . . . . ?
C2 C1 N1 Cu1 -5.5(7) . . . . ?
Br1 Cu1 N1 C7 56.0(5) 1_655 . . . ?
Br1 Cu1 N1 C7 -132.3(4) . . . . ?
Br1 Cu1 N1 C1 -116.4(3) 1_655 . . . ?
Br1 Cu1 N1 C1 55.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.98
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.071
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1038362'
_audit_update_record             
;
2014-12-09 deposited with the CCDC.
2015-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H18 Br4 Cu N4 O2'
_chemical_formula_sum            'C26 H18 Br4 Cu N4 O2'
_chemical_formula_weight         801.62

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_HALL  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.974(5)
_cell_length_b                   9.060(5)
_cell_length_c                   9.663(5)
_cell_angle_alpha                81.395(5)
_cell_angle_beta                 73.778(5)
_cell_angle_gamma                83.536(5)
_cell_volume                     660.9(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    940
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      21.95

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            BLACK
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.014
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             387
_exptl_absorpt_coefficient_mu    6.905
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.2996
_exptl_absorpt_correction_T_max  0.3250
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4738
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0715
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2309
_reflns_number_gt                1500
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0966P)²+1.7352P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2309
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.1850
_refine_ls_wR_factor_gt          0.1599
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.0000 0.5000 0.5000 0.0371(5) Uani 1 2 d S . .
Br1 Br 0.87861(16) 0.27606(13) 0.64735(11) 0.0607(4) Uani 1 1 d . . .
Br2 Br 0.29651(17) 1.07863(14) 0.84986(14) 0.0749(5) Uani 1 1 d . . .
O1 O 0.8858(8) 0.7485(7) 0.8491(6) 0.0377(15) Uani 1 1 d . . .
C4 C 1.2774(14) 0.5805(12) 0.9574(11) 0.050(3) Uani 1 1 d . . .
H4 H 1.3437 0.5817 1.0225 0.059 Uiso 1 1 calc R . .
C13 C 0.6321(12) 0.7067(11) 0.5958(10) 0.043(2) Uani 1 1 d . . .
H13 H 0.6963 0.6283 0.5478 0.051 Uiso 1 1 calc R . .
N1 N 0.9685(10) 0.5959(8) 0.6780(7) 0.0358(17) Uani 1 1 d . . .
C6 C 1.0397(12) 0.6688(10) 0.8638(10) 0.037(2) Uani 1 1 d . . .
C8 C 0.6931(12) 0.7599(10) 0.6987(9) 0.037(2) Uani 1 1 d . . .
N2 N 0.2229(10) 0.9340(9) 0.6045(9) 0.053(2) Uani 1 1 d . . .
H2A H 0.1882 0.8979 0.5407 0.063 Uiso 1 1 calc R . .
H2B H 0.1602 1.0046 0.6497 0.063 Uiso 1 1 calc R . .
C11 C 0.3758(12) 0.8798(10) 0.6336(10) 0.041(2) Uani 1 1 d . . .
C9 C 0.5907(12) 0.8743(10) 0.7723(10) 0.043(2) Uani 1 1 d . . .
H9 H 0.6270 0.9127 0.8423 0.051 Uiso 1 1 calc R . .
C1 C 1.0923(11) 0.5720(10) 0.7591(9) 0.034(2) Uani 1 1 d . . .
C7 C 0.8512(11) 0.6990(10) 0.7341(9) 0.035(2) Uani 1 1 d . . .
C5 C 1.1286(14) 0.6772(11) 0.9661(10) 0.048(3) Uani 1 1 d . . .
H5 H 1.0911 0.7430 1.0357 0.057 Uiso 1 1 calc R . .
C2 C 1.2373(13) 0.4732(11) 0.7539(10) 0.044(2) Uani 1 1 d . . .
H2 H 1.2713 0.4045 0.6869 0.053 Uiso 1 1 calc R . .
C3 C 1.3302(13) 0.4814(13) 0.8535(11) 0.052(3) Uani 1 1 d . . .
H3 H 1.4313 0.4186 0.8511 0.063 Uiso 1 1 calc R . .
C10 C 0.4359(13) 0.9300(10) 0.7407(10) 0.043(2) Uani 1 1 d . . .
C12 C 0.4816(12) 0.7655(11) 0.5630(10) 0.044(2) Uani 1 1 d . . .
H12 H 0.4479 0.7283 0.4911 0.053 Uiso 1 1 calc R . .


_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 N1 1.983(7) . ?
Cu1 N1 1.983(7) 2_766 ?
Cu1 Br1 2.4266(15) 2_766 ?
Cu1 Br1 2.4266(15) . ?
Br2 C10 1.896(9) . ?
O1 C7 1.364(10) . ?
O1 C6 1.383(10) . ?
C4 C5 1.384(14) . ?
C4 C3 1.392(14) . ?
C4 H4 0.9300 . ?
C13 C12 1.358(13) . ?
C13 C8 1.387(12) . ?
C13 H13 0.9300 . ?
N1 C7 1.309(11) . ?
N1 C1 1.403(11) . ?
C6 C1 1.384(12) . ?
C6 C5 1.383(12) . ?
C8 C9 1.397(11) . ?
C8 C7 1.428(12) . ?
N2 C11 1.350(11) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C11 C12 1.394(12) . ?
C11 C10 1.405(13) . ?
C9 C10 1.376(13) . ?
C9 H9 0.9300 . ?
C1 C2 1.375(12) . ?
C5 H5 0.9300 . ?
C2 C3 1.383(13) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C12 H12 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
N1 Cu1 N1 180.000(1) . 2_766 ?
N1 Cu1 Br1 89.9(2) . 2_766 ?
N1 Cu1 Br1 90.1(2) 2_766 2_766 ?
N1 Cu1 Br1 90.1(2) . . ?
N1 Cu1 Br1 89.9(2) 2_766 . ?
Br1 Cu1 Br1 180.0 2_766 . ?
C7 O1 C6 105.2(6) . . ?
C5 C4 C3 121.6(9) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C12 C13 C8 122.0(8) . . ?
C12 C13 H13 119.0 . . ?
C8 C13 H13 119.0 . . ?
C7 N1 C1 107.0(7) . . ?
C7 N1 Cu1 130.4(6) . . ?
C1 N1 Cu1 122.1(5) . . ?
C1 C6 C5 123.7(9) . . ?
C1 C6 O1 108.6(7) . . ?
C5 C6 O1 127.7(8) . . ?
C13 C8 C9 117.6(8) . . ?
C13 C8 C7 122.5(8) . . ?
C9 C8 C7 119.9(8) . . ?
C11 N2 H2A 120.0 . . ?
C11 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N2 C11 C12 122.0(9) . . ?
N2 C11 C10 122.6(9) . . ?
C12 C11 C10 115.4(8) . . ?
C10 C9 C8 119.7(8) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C6 C1 C2 120.8(8) . . ?
C6 C1 N1 106.6(7) . . ?
C2 C1 N1 132.6(8) . . ?
N1 C7 O1 112.6(7) . . ?
N1 C7 C8 130.5(8) . . ?
O1 C7 C8 116.8(7) . . ?
C6 C5 C4 115.1(9) . . ?
C6 C5 H5 122.4 . . ?
C4 C5 H5 122.4 . . ?
C3 C2 C1 116.5(8) . . ?
C3 C2 H2 121.8 . . ?
C1 C2 H2 121.8 . . ?
C2 C3 C4 122.3(9) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C9 C10 C11 123.0(8) . . ?
C9 C10 Br2 118.1(7) . . ?
C11 C10 Br2 118.9(7) . . ?
C13 C12 C11 122.2(9) . . ?
C13 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?

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
N1 Cu1 N1 C7 -176(100) 2_766 . . . ?
Br1 Cu1 N1 C7 76.0(8) 2_766 . . . ?
Br1 Cu1 N1 C7 -104.0(8) . . . . ?
N1 Cu1 N1 C1 12(100) 2_766 . . . ?
Br1 Cu1 N1 C1 -96.0(7) 2_766 . . . ?
Br1 Cu1 N1 C1 84.0(7) . . . . ?
C7 O1 C6 C1 -1.0(10) . . . . ?
C7 O1 C6 C5 -179.3(10) . . . . ?
C12 C13 C8 C9 2.0(15) . . . . ?
C12 C13 C8 C7 -180.0(10) . . . . ?
C13 C8 C9 C10 -0.2(15) . . . . ?
C7 C8 C9 C10 -178.2(9) . . . . ?
C5 C6 C1 C2 1.9(15) . . . . ?
O1 C6 C1 C2 -176.5(8) . . . . ?
C5 C6 C1 N1 179.4(9) . . . . ?
O1 C6 C1 N1 1.0(10) . . . . ?
C7 N1 C1 C6 -0.7(10) . . . . ?
Cu1 N1 C1 C6 172.9(6) . . . . ?
C7 N1 C1 C2 176.5(10) . . . . ?
Cu1 N1 C1 C2 -10.0(14) . . . . ?
C1 N1 C7 O1 0.1(10) . . . . ?
Cu1 N1 C7 O1 -172.8(6) . . . . ?
C1 N1 C7 C8 -176.4(10) . . . . ?
Cu1 N1 C7 C8 10.7(15) . . . . ?
C6 O1 C7 N1 0.5(10) . . . . ?
C6 O1 C7 C8 177.6(8) . . . . ?
C13 C8 C7 N1 4.1(16) . . . . ?
C9 C8 C7 N1 -177.9(10) . . . . ?
C13 C8 C7 O1 -172.3(9) . . . . ?
C9 C8 C7 O1 5.7(13) . . . . ?
C1 C6 C5 C4 0.0(15) . . . . ?
O1 C6 C5 C4 178.1(9) . . . . ?
C3 C4 C5 C6 -0.8(15) . . . . ?
C6 C1 C2 C3 -2.9(14) . . . . ?
N1 C1 C2 C3 -179.7(10) . . . . ?
C1 C2 C3 C4 2.1(16) . . . . ?
C5 C4 C3 C2 -0.3(17) . . . . ?
C8 C9 C10 C11 -1.7(16) . . . . ?
C8 C9 C10 Br2 177.1(7) . . . . ?
N2 C11 C10 C9 179.3(10) . . . . ?
C12 C11 C10 C9 1.7(15) . . . . ?
N2 C11 C10 Br2 0.5(13) . . . . ?
C12 C11 C10 Br2 -177.1(7) . . . . ?
C8 C13 C12 C11 -2.0(16) . . . . ?
N2 C11 C12 C13 -177.4(10) . . . . ?
C10 C11 C12 C13 0.1(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         2.542
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.144
