# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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 1449499'
_audit_update_record             
;
2016-01-23 deposited with the CCDC.
2017-04-21 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 Cl2 Cu N8 O, 2(H2 O)'
_chemical_formula_sum            'C18 H22 Cl2 Cu N8 O3'
_chemical_formula_weight         532.88

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'
Cl Cl 0.1484 0.1585 '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'
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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'A b a 2'
_symmetry_space_group_name_Hall  'A 2 -2ac'

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

_cell_length_a                   17.6722(7)
_cell_length_b                   17.3463(7)
_cell_length_c                   7.3970(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2267.53(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5498
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      27.51

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1092
_exptl_absorpt_coefficient_mu    1.237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6060
_exptl_absorpt_correction_T_max  0.9184
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Nonius X8Apex CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 25
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8268
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         27.53
_reflns_number_total             2162
_reflns_number_gt                2046
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_structure_solution    'SHELXTL (Bruker, 2004)'
_computing_structure_refinement  'SHELXTL (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2004)'
_computing_publication_material  'SHELXTL (Bruker, 2004)'

_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)+(0.0499P)²+0.7128P] 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   0.16(2)
_refine_ls_number_reflns         2162
_refine_ls_number_parameters     157
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0763
_refine_ls_wR_factor_gt          0.0753
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.170
_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 0.5000 1.0000 0.76509(11) 0.03503(13) Uani 1 2 d S . .
Cl1 Cl 0.47662(4) 0.89161(4) 0.95223(13) 0.0505(2) Uani 1 1 d . . .
O1W O 0.5000 1.0000 0.4923(7) 0.0955(17) Uani 1 2 d SDU . .
O2W O 0.38879(14) 0.9475(3) 0.2989(4) 0.0867(11) Uani 1 1 d D . .
N1 N 0.61030(11) 0.97492(13) 0.7429(4) 0.0385(5) Uani 1 1 d . . .
N2 N 0.73762(12) 0.99293(13) 0.7557(7) 0.0470(6) Uani 1 1 d . . .
N3 N 0.71963(12) 0.92260(13) 0.6823(3) 0.0386(5) Uani 1 1 d . . .
N4 N 0.62832(13) 0.84314(13) 0.6056(4) 0.0449(6) Uani 1 1 d . . .
C1 C 0.67067(15) 1.02116(16) 0.7856(5) 0.0448(7) Uani 1 1 d . . .
H1 H 0.6640 1.0703 0.8334 0.054 Uiso 1 1 calc R . .
C2 C 0.64472(14) 0.91306(15) 0.6761(4) 0.0365(5) Uani 1 1 d . . .
C3 C 0.75618(16) 0.85662(16) 0.6180(4) 0.0435(6) Uani 1 1 d . . .
C4 C 0.83193(19) 0.8377(2) 0.5978(5) 0.0581(9) Uani 1 1 d . . .
H4 H 0.8705 0.8718 0.6274 0.070 Uiso 1 1 calc R . .
C5 C 0.8463(2) 0.7651(2) 0.5314(6) 0.0712(11) Uani 1 1 d . . .
H5 H 0.8962 0.7495 0.5162 0.085 Uiso 1 1 calc R . .
C6 C 0.7887(3) 0.7146(3) 0.4864(7) 0.0760(13) Uani 1 1 d . . .
H6 H 0.8012 0.6660 0.4422 0.091 Uiso 1 1 calc R . .
C7 C 0.7125(2) 0.73392(19) 0.5052(6) 0.0631(10) Uani 1 1 d . . .
H7 H 0.6740 0.6998 0.4745 0.076 Uiso 1 1 calc R . .
C8 C 0.69769(18) 0.80679(17) 0.5721(5) 0.0479(7) Uani 1 1 d . . .
C9 C 0.5544(2) 0.8108(2) 0.5628(7) 0.0737(13) Uani 1 1 d . . .
H9A H 0.5186 0.8518 0.5469 0.111 Uiso 1 1 calc R . .
H9B H 0.5382 0.7780 0.6599 0.111 Uiso 1 1 calc R . .
H9C H 0.5578 0.7813 0.4533 0.111 Uiso 1 1 calc R . .
H1W H 0.4645(8) 0.994(3) 0.425(5) 0.111 Uiso 1 1 d D . .
H2WB H 0.408(3) 0.935(3) 0.202(5) 0.111 Uiso 1 1 d D . .
H2WA H 0.3455(15) 0.959(3) 0.267(7) 0.111 Uiso 1 1 d 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
Cu1 N1 2.004(2) . ?
Cu1 N1 2.004(2) 2_675 ?
Cu1 O1W 2.018(6) . ?
Cu1 Cl1 2.3710(9) . ?
Cu1 Cl1 2.3710(9) 2_675 ?
O1W H1W 0.81(2) . ?
O2W H2WB 0.83(2) . ?
O2W H2WA 0.82(2) . ?
N1 C2 1.329(3) . ?
N1 C1 1.372(3) . ?
N2 C1 1.299(4) . ?
N2 N3 1.373(3) . ?
N3 C2 1.335(3) . ?
N3 C3 1.397(4) . ?
N4 C2 1.352(3) . ?
N4 C8 1.401(4) . ?
N4 C9 1.456(4) . ?
C1 H1 0.9300 . ?
C3 C4 1.387(4) . ?
C3 C8 1.390(4) . ?
C4 C5 1.375(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.394(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.383(5) . ?
C7 H7 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

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 170.61(17) . 2_675 ?
N1 Cu1 O1W 85.30(9) . . ?
N1 Cu1 O1W 85.30(9) 2_675 . ?
N1 Cu1 Cl1 92.59(8) . . ?
N1 Cu1 Cl1 92.89(7) 2_675 . ?
O1W Cu1 Cl1 125.72(3) . . ?
N1 Cu1 Cl1 92.89(7) . 2_675 ?
N1 Cu1 Cl1 92.59(8) 2_675 2_675 ?
O1W Cu1 Cl1 125.72(3) . 2_675 ?
Cl1 Cu1 Cl1 108.56(6) . 2_675 ?
Cu1 O1W H1W 128(2) . . ?
H2WB O2W H2WA 101(3) . . ?
C2 N1 C1 101.6(2) . . ?
C2 N1 Cu1 130.62(17) . . ?
C1 N1 Cu1 127.65(19) . . ?
C1 N2 N3 101.0(2) . . ?
C2 N3 N2 110.7(2) . . ?
C2 N3 C3 110.2(2) . . ?
N2 N3 C3 139.0(2) . . ?
C2 N4 C8 106.5(2) . . ?
C2 N4 C9 128.5(2) . . ?
C8 N4 C9 124.9(3) . . ?
N2 C1 N1 116.7(3) . . ?
N2 C1 H1 121.7 . . ?
N1 C1 H1 121.7 . . ?
N1 C2 N3 110.0(2) . . ?
N1 C2 N4 140.4(2) . . ?
N3 C2 N4 109.7(2) . . ?
C4 C3 C8 123.0(3) . . ?
C4 C3 N3 132.6(3) . . ?
C8 C3 N3 104.4(2) . . ?
C5 C4 C3 115.7(4) . . ?
C5 C4 H4 122.1 . . ?
C3 C4 H4 122.1 . . ?
C4 C5 C6 122.0(3) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C7 122.3(3) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C8 C7 C6 116.1(4) . . ?
C8 C7 H7 122.0 . . ?
C6 C7 H7 122.0 . . ?
C7 C8 C3 121.0(3) . . ?
C7 C8 N4 129.9(3) . . ?
C3 C8 N4 109.1(2) . . ?
N4 C9 H9A 109.5 . . ?
N4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1W O2W 0.81(2) 1.82(2) 2.596(4) 161(5) .
O2W H2WA N2 0.82(2) 2.09(2) 2.882(3) 163(6) 4_474
O2W H2WB Cl1 0.83(2) 2.33(2) 3.151(3) 172(5) 1_554

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.744
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_li003
_database_code_depnum_ccdc_archive 'CCDC 1508941'
_audit_update_record             
;
2016-10-09 deposited with the CCDC.
2017-04-21 downloaded from the CCDC.
;
_audit_creation_date             2016-10-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 Br2 Cu N8 O, 2(H2 O)'
_chemical_formula_sum            'C18 H22 Br2 Cu N8 O3'
_chemical_formula_weight         621.79
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.028(3)
_cell_length_b                   7.2842(12)
_cell_length_c                   17.278(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.963(10)
_cell_angle_gamma                90
_cell_volume                     2265.9(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2394
_cell_measurement_temperature    303
_cell_measurement_theta_max      64.64
_cell_measurement_theta_min      4.91
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.825
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0745 before and 0.0467 after correction.
The Ratio of minimum to maximum transmission is 0.8141.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1236
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   0.7526
_exptl_transmission_factor_min   0.6127
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5096
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        65.042
_diffrn_reflns_theta_max         65.042
_diffrn_reflns_theta_min         4.913
_diffrn_ambient_temperature      303
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1525
_reflns_number_total             1892
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.829
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.113
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         1892
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0551
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0247P)²+39.6033P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1452
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O2W(H2WA,H2WB)
2.b Rotating group:
 O1W(H1W)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.7595(2) 0.7500 0.0441(4) Uani 1 2 d S T P . .
Br1 Br 0.39502(5) 0.97972(14) 0.77692(5) 0.0567(3) Uani 1 1 d . . . . .
O1W O 0.5000 0.4856(13) 0.7500 0.112(5) Uani 1 2 d S T P . .
H1W H 0.4888 0.4429 0.7135 0.168 Uiso 1 1 d GR . . . .
N1 N 0.4666(3) 0.7378(10) 0.6374(3) 0.0457(16) Uani 1 1 d . . . . .
N2 N 0.4762(4) 0.7428(12) 0.5066(4) 0.059(2) Uani 1 1 d . . . . .
N3 N 0.4097(3) 0.6677(10) 0.5262(3) 0.0471(17) Uani 1 1 d . . . . .
N4 N 0.3384(3) 0.5962(10) 0.6212(4) 0.0468(16) Uani 1 1 d . . . . .
C1 C 0.5071(5) 0.7792(13) 0.5750(4) 0.056(2) Uani 1 1 d . . . . .
H1 H 0.5542 0.8307 0.5809 0.067 Uiso 1 1 calc R . . . .
C2 C 0.4049(4) 0.6671(11) 0.6035(4) 0.0423(18) Uani 1 1 d . . . . .
C3 C 0.3462(5) 0.5961(12) 0.4889(5) 0.050(2) Uani 1 1 d . . . . .
C4 C 0.3233(5) 0.5718(14) 0.4125(5) 0.063(3) Uani 1 1 d . . . . .
H4 H 0.3533 0.6034 0.3724 0.075 Uiso 1 1 calc R . . . .
C5 C 0.2535(6) 0.4979(14) 0.3987(5) 0.067(3) Uani 1 1 d . . . . .
H5 H 0.2364 0.4768 0.3478 0.081 Uiso 1 1 calc R . . . .
C6 C 0.2079(5) 0.4539(14) 0.4586(6) 0.066(3) Uani 1 1 d . . . . .
H6 H 0.1609 0.4056 0.4468 0.079 Uiso 1 1 calc R . . . .
C7 C 0.2311(5) 0.4806(13) 0.5352(5) 0.058(2) Uani 1 1 d . . . . .
H7 H 0.2006 0.4511 0.5752 0.070 Uiso 1 1 calc R . . . .
C8 C 0.3009(4) 0.5526(11) 0.5501(4) 0.0461(19) Uani 1 1 d . . . . .
C9 C 0.3127(5) 0.5494(15) 0.6986(5) 0.063(3) Uani 1 1 d . . . . .
H9A H 0.3193 0.4203 0.7077 0.095 Uiso 1 1 calc GR . . . .
H9B H 0.2611 0.5802 0.7009 0.095 Uiso 1 1 calc GR . . . .
H9C H 0.3411 0.6173 0.7374 0.095 Uiso 1 1 calc GR . . . .
O2W O 0.4506(4) 0.2654(9) 0.6363(3) 0.0632(17) Uani 1 1 d . . . . .
H2WA H 0.4467 0.1632 0.6594 0.095 Uiso 1 1 d G . . . .
H2WB H 0.4902 0.2662 0.6116 0.095 Uiso 1 1 d G . . . .


_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 Br1 2.5419(14) 2_656 ?
Cu1 Br1 2.5419(14) . ?
Cu1 O1W 1.995(9) . ?
Cu1 N1 2.013(6) . ?
Cu1 N1 2.013(6) 2_656 ?
O1W H1W 0.7225 . ?
N1 C1 1.366(10) . ?
N1 C2 1.333(9) . ?
N2 N3 1.375(9) . ?
N2 C1 1.307(10) . ?
N3 C2 1.343(9) . ?
N3 C3 1.387(10) . ?
N4 C2 1.355(9) . ?
N4 C8 1.406(9) . ?
N4 C9 1.477(10) . ?
C1 H1 0.9300 . ?
C3 C4 1.373(11) . ?
C3 C8 1.405(11) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(13) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(14) . ?
C6 H6 0.9300 . ?
C6 C7 1.380(12) . ?
C7 H7 0.9300 . ?
C7 C8 1.377(11) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
O2W H2WA 0.8499 . ?
O2W H2WB 0.8498 . ?

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
Br1 Cu1 Br1 101.76(8) 2_656 . ?
O1W Cu1 Br1 129.12(4) . . ?
O1W Cu1 Br1 129.12(4) . 2_656 ?
O1W Cu1 N1 85.5(2) . . ?
O1W Cu1 N1 85.5(2) . 2_656 ?
N1 Cu1 Br1 92.19(19) 2_656 2_656 ?
N1 Cu1 Br1 92.19(19) . . ?
N1 Cu1 Br1 93.50(19) . 2_656 ?
N1 Cu1 Br1 93.50(19) 2_656 . ?
N1 Cu1 N1 171.0(4) . 2_656 ?
Cu1 O1W H1W 115.5 . . ?
C1 N1 Cu1 126.9(5) . . ?
C2 N1 Cu1 130.9(5) . . ?
C2 N1 C1 101.9(6) . . ?
C1 N2 N3 101.1(6) . . ?
N2 N3 C3 138.1(6) . . ?
C2 N3 N2 110.4(6) . . ?
C2 N3 C3 111.5(7) . . ?
C2 N4 C8 106.3(6) . . ?
C2 N4 C9 127.9(6) . . ?
C8 N4 C9 125.4(7) . . ?
N1 C1 H1 121.7 . . ?
N2 C1 N1 116.7(7) . . ?
N2 C1 H1 121.7 . . ?
N1 C2 N3 109.8(7) . . ?
N1 C2 N4 141.0(7) . . ?
N3 C2 N4 109.2(6) . . ?
N3 C3 C8 103.5(6) . . ?
C4 C3 N3 134.0(8) . . ?
C4 C3 C8 122.5(8) . . ?
C3 C4 H4 121.9 . . ?
C3 C4 C5 116.3(9) . . ?
C5 C4 H4 121.9 . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 122.0(8) . . ?
C6 C5 H5 119.0 . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.3(8) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 121.3 . . ?
C8 C7 C6 117.5(9) . . ?
C8 C7 H7 121.3 . . ?
C3 C8 N4 109.6(7) . . ?
C7 C8 N4 130.0(8) . . ?
C7 C8 C3 120.4(7) . . ?
N4 C9 H9A 109.5 . . ?
N4 C9 H9B 109.5 . . ?
N4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
H2WA O2W H2WB 109.4 . . ?

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
Cu1 N1 C1 N2 175.4(7) . . . . ?
Cu1 N1 C2 N3 -174.4(6) . . . . ?
Cu1 N1 C2 N4 6.5(17) . . . . ?
N2 N3 C2 N1 -0.7(10) . . . . ?
N2 N3 C2 N4 178.7(7) . . . . ?
N2 N3 C3 C4 -0.5(18) . . . . ?
N2 N3 C3 C8 -177.8(9) . . . . ?
N3 N2 C1 N1 -1.0(11) . . . . ?
N3 C3 C4 C5 -178.3(10) . . . . ?
N3 C3 C8 N4 -0.8(9) . . . . ?
N3 C3 C8 C7 178.5(8) . . . . ?
C1 N1 C2 N3 0.1(9) . . . . ?
C1 N1 C2 N4 -179.0(11) . . . . ?
C1 N2 N3 C2 1.0(10) . . . . ?
C1 N2 N3 C3 179.4(10) . . . . ?
C2 N1 C1 N2 0.7(11) . . . . ?
C2 N3 C3 C4 178.0(10) . . . . ?
C2 N3 C3 C8 0.6(9) . . . . ?
C2 N4 C8 C3 0.7(9) . . . . ?
C2 N4 C8 C7 -178.6(9) . . . . ?
C3 N3 C2 N1 -179.6(7) . . . . ?
C3 N3 C2 N4 -0.2(10) . . . . ?
C3 C4 C5 C6 1.4(15) . . . . ?
C4 C3 C8 N4 -178.5(8) . . . . ?
C4 C3 C8 C7 0.8(14) . . . . ?
C4 C5 C6 C7 -0.7(16) . . . . ?
C5 C6 C7 C8 0.1(15) . . . . ?
C6 C7 C8 N4 179.1(8) . . . . ?
C6 C7 C8 C3 -0.1(13) . . . . ?
C8 N4 C2 N1 178.8(11) . . . . ?
C8 N4 C2 N3 -0.3(9) . . . . ?
C8 C3 C4 C5 -1.4(14) . . . . ?
C9 N4 C2 N1 -8.7(18) . . . . ?
C9 N4 C2 N3 172.2(8) . . . . ?
C9 N4 C8 C3 -172.0(8) . . . . ?
C9 N4 C8 C7 8.7(14) . . . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
