# 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 2021

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1887427'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples? Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2018-12-27 deposited with the CCDC.	2021-06-09 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         'C10 H15 Br2 Cu N5 O, H2 O'
_chemical_formula_sum            'C10 H17 Br2 Cu N5 O2'
_chemical_formula_weight         462.64

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.5320(17)
_cell_length_b                   15.288(3)
_cell_length_c                   12.596(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.570(3)
_cell_angle_gamma                90
_cell_volume                     1566.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3031
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      27.54

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.962
_exptl_crystal_F_000             908
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    6.504
_shelx_estimated_absorpt_T_min   0.216
_shelx_estimated_absorpt_T_max   0.387
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.563
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12463
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.157
_diffrn_reflns_theta_max         28.399
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3929
_reflns_number_gt                2915
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR_92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0324P)²+0.5969P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3929
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0702
_refine_ls_wR_factor_gt          0.0625
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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 0.38619(5) 0.63913(3) 0.65972(3) 0.01794(10) Uani 1 1 d . . . . .
Br1 Br 0.16461(4) 0.75913(2) 0.60553(3) 0.02284(9) Uani 1 1 d . . . . .
Br2 Br 0.63377(4) 0.70184(3) 0.77898(3) 0.03050(10) Uani 1 1 d . . . . .
O1 O 0.3546(3) 0.63871(18) 0.8951(2) 0.0312(6) Uani 1 1 d . . . . .
H1O H 0.430(5) 0.666(3) 0.896(3) 0.039(13) Uiso 1 1 d . . . . .
N1 N 0.3221(3) 0.59667(18) 0.7934(2) 0.0208(6) Uani 1 1 d . . . . .
N2 N 0.2654(3) 0.52892(17) 0.6065(2) 0.0172(5) Uani 1 1 d . . . . .
N3 N 0.2659(3) 0.50324(19) 0.5045(2) 0.0193(6) Uani 1 1 d . . . . .
H3N H 0.216(4) 0.463(2) 0.474(3) 0.019(10) Uiso 1 1 d . . . . .
N4 N 0.4136(3) 0.63070(16) 0.5045(2) 0.0168(5) Uani 1 1 d . . . . .
N5 N 0.3265(3) 0.53648(17) 0.3452(2) 0.0184(6) Uani 1 1 d . . . . .
C1 C 0.2247(4) 0.5307(2) 0.7794(3) 0.0195(7) Uani 1 1 d . . . . .
C2 C 0.1965(3) 0.4875(2) 0.6696(2) 0.0175(6) Uani 1 1 d . . . . .
C3 C 0.3394(4) 0.5596(2) 0.4493(3) 0.0176(6) Uani 1 1 d . . . . .
C4 C 0.4822(4) 0.6859(2) 0.4462(3) 0.0199(7) Uani 1 1 d . . . . .
C5 C 0.4790(4) 0.6653(2) 0.3389(3) 0.0202(7) Uani 1 1 d . . . . .
H5 H 0.520(4) 0.700(2) 0.298(3) 0.019(9) Uiso 1 1 d . . . . .
C6 C 0.3980(4) 0.5907(2) 0.2893(2) 0.0189(7) Uani 1 1 d . . . . .
C7 C 0.1490(4) 0.4962(2) 0.8633(3) 0.0304(8) Uani 1 1 d . . . . .
H7A H 0.0290 0.4958 0.8314 0.036 Uiso 1 1 calc R U . . .
H7B H 0.1802 0.5335 0.9296 0.036 Uiso 1 1 calc R U . . .
H7C H 0.1880 0.4364 0.8840 0.036 Uiso 1 1 calc R U . . .
C8 C 0.1040(4) 0.4038(2) 0.6409(3) 0.0245(7) Uani 1 1 d . . . . .
H8A H 0.0075 0.4054 0.6677 0.029 Uiso 1 1 calc R U . . .
H8B H 0.1753 0.3550 0.6763 0.029 Uiso 1 1 calc R U . . .
H8C H 0.0685 0.3959 0.5600 0.029 Uiso 1 1 calc R U . . .
C9 C 0.5536(4) 0.7701(2) 0.4997(3) 0.0280(8) Uani 1 1 d . . . . .
H9A H 0.6513 0.7580 0.5627 0.034 Uiso 1 1 calc R U . . .
H9B H 0.4719 0.8010 0.5262 0.034 Uiso 1 1 calc R U . . .
H9C H 0.5844 0.8066 0.4452 0.034 Uiso 1 1 calc R U . . .
C10 C 0.3745(4) 0.5677(2) 0.1700(3) 0.0251(7) Uani 1 1 d . . . . .
H10A H 0.3422 0.5061 0.1575 0.030 Uiso 1 1 calc R U . . .
H10B H 0.4776 0.5771 0.1525 0.030 Uiso 1 1 calc R U . . .
H10C H 0.2882 0.6047 0.1219 0.030 Uiso 1 1 calc R U . . .
O1W O 0.1039(3) 0.37829(18) 0.3584(2) 0.0337(6) Uani 1 1 d . . . . .
H1W H 0.043(6) 0.338(3) 0.365(4) 0.065(16) Uiso 1 1 d . . . . .
H2W H 0.164(5) 0.362(3) 0.322(3) 0.038(12) Uiso 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
Cu1 N2 1.983(3) . ?
Cu1 N1 2.028(3) . ?
Cu1 N4 2.042(2) . ?
Cu1 Br2 2.3920(6) . ?
Cu1 Br1 2.5741(6) . ?
O1 N1 1.384(3) . ?
O1 H1O 0.77(4) . ?
N1 C1 1.285(4) . ?
N2 C2 1.289(4) . ?
N2 N3 1.345(3) . ?
N3 C3 1.373(4) . ?
N3 H3N 0.78(3) . ?
N4 C3 1.342(4) . ?
N4 C4 1.362(4) . ?
N5 C3 1.330(4) . ?
N5 C6 1.347(4) . ?
C1 C2 1.485(4) . ?
C1 C7 1.491(4) . ?
C2 C8 1.489(4) . ?
C4 C5 1.379(4) . ?
C4 C9 1.495(5) . ?
C5 C6 1.381(5) . ?
C5 H5 0.88(3) . ?
C6 C10 1.497(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
O1W H1W 0.83(5) . ?
O1W H2W 0.82(4) . ?

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
N2 Cu1 N1 76.46(10) . . ?
N2 Cu1 N4 79.68(10) . . ?
N1 Cu1 N4 155.85(11) . . ?
N2 Cu1 Br2 145.40(7) . . ?
N1 Cu1 Br2 90.87(8) . . ?
N4 Cu1 Br2 106.96(7) . . ?
N2 Cu1 Br1 104.51(7) . . ?
N1 Cu1 Br1 95.03(8) . . ?
N4 Cu1 Br1 94.49(7) . . ?
Br2 Cu1 Br1 108.63(2) . . ?
N1 O1 H1O 102(3) . . ?
C1 N1 O1 115.7(3) . . ?
C1 N1 Cu1 117.5(2) . . ?
O1 N1 Cu1 126.2(2) . . ?
C2 N2 N3 125.4(3) . . ?
C2 N2 Cu1 119.8(2) . . ?
N3 N2 Cu1 114.8(2) . . ?
N2 N3 C3 115.8(3) . . ?
N2 N3 H3N 123(3) . . ?
C3 N3 H3N 120(3) . . ?
C3 N4 C4 115.7(3) . . ?
C3 N4 Cu1 112.04(19) . . ?
C4 N4 Cu1 132.1(2) . . ?
C3 N5 C6 115.8(3) . . ?
N1 C1 C2 113.2(3) . . ?
N1 C1 C7 125.5(3) . . ?
C2 C1 C7 121.3(3) . . ?
N2 C2 C1 112.3(3) . . ?
N2 C2 C8 125.4(3) . . ?
C1 C2 C8 122.2(3) . . ?
N5 C3 N4 127.8(3) . . ?
N5 C3 N3 114.7(3) . . ?
N4 C3 N3 117.5(3) . . ?
N4 C4 C5 120.2(3) . . ?
N4 C4 C9 118.2(3) . . ?
C5 C4 C9 121.5(3) . . ?
C6 C5 C4 119.4(3) . . ?
C6 C5 H5 118(2) . . ?
C4 C5 H5 123(2) . . ?
N5 C6 C5 121.0(3) . . ?
N5 C6 C10 115.8(3) . . ?
C5 C6 C10 123.1(3) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
H1W O1W H2W 111(4) . . ?

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
O1 H1O Br2 0.77(4) 2.65(4) 3.293(3) 142(4) .
N3 H3N O1W 0.78(3) 1.97(4) 2.722(4) 163(3) .
O1W H1W Br1 0.83(5) 2.42(5) 3.240(3) 170(4) 3_566
O1W H2W Br2 0.82(4) 2.62(4) 3.442(3) 174(4) 3_666

_refine_diff_density_max         0.676
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.110

####################################################################### 
# 
# 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_II
_database_code_depnum_ccdc_archive 'CCDC 1887428'
loop_
_audit_author_name
_audit_author_address
'Victor Khrustalev'
;Peoples? Friendship University of Russia (RUDN University, Moscow)
Russia
;
_audit_update_record             
;
2018-12-27 deposited with the CCDC.	2021-06-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H15 Cl2 Cu N5 O'
_chemical_formula_sum            'C10 H15 Cl2 Cu N5 O'
_chemical_formula_weight         355.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0070 0.0030 '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 0.2280 0.2890 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.0180 2.1450 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0130 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0210 0.0120 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.8717(14)
_cell_length_b                   23.169(5)
_cell_length_c                   9.1083(18)
_cell_angle_alpha                90
_cell_angle_beta                 93.73(3)
_cell_angle_gamma                90
_cell_volume                     1447.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    600
_cell_measurement_theta_min      4.4
_cell_measurement_theta_max      33.3

_exptl_crystal_description       plate
_exptl_crystal_colour            brown-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_F_000             724
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    4.286
_shelx_estimated_absorpt_T_min   0.360
_shelx_estimated_absorpt_T_max   0.919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.330
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_process_details   'Scala (Evans, 2006)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.96260
_diffrn_radiation_type           synchrotron
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rayonix SX165 CCD'
_diffrn_measurement_method       /f
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10681
_diffrn_reflns_av_unetI/netI     0.215
_diffrn_reflns_av_R_equivalents  0.119
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.198
_diffrn_reflns_theta_max         38.282
_diffrn_reflns_theta_full        35.279
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             3031
_reflns_number_gt                2170
_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       'Marccd (Doyle, 2011)'
_computing_cell_refinement       'iMosflm (Battye et al., 2011)'
_computing_data_reduction        iMosflm
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2015)'
_computing_publication_material  SHELXTL

_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)+(0.01P)²+0.7P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0050(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3031
_refine_ls_number_parameters     181
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1214
_refine_ls_R_factor_gt           0.1079
_refine_ls_wR_factor_ref         0.2507
_refine_ls_wR_factor_gt          0.2330
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.60612(8) 0.58726(3) 0.63743(8) 0.0335(4) Uani 1 1 d . . . . .
Cl1 Cl 0.79109(17) 0.62028(7) 0.86197(15) 0.0357(5) Uani 1 1 d . . . . .
Cl2 Cl 0.85445(18) 0.57648(7) 0.48523(17) 0.0385(5) Uani 1 1 d . . . . .
O1 O 0.7565(5) 0.46073(19) 0.6422(5) 0.0416(11) Uani 1 1 d D . . . .
H1 H 0.828(10) 0.478(3) 0.575(7) 0.09(3) Uiso 1 1 d D . . . .
N1 N 0.6096(6) 0.5001(2) 0.6774(6) 0.0348(12) Uani 1 1 d . . . . .
N2 N 0.3536(6) 0.5728(2) 0.7331(5) 0.0323(11) Uani 1 1 d . . . . .
N3 N 0.2373(6) 0.6199(2) 0.7448(5) 0.0359(12) Uani 1 1 d . . . . .
H3 H 0.1317 0.6192 0.7944 0.043 Uiso 1 1 calc R U . . .
N4 N 0.4649(6) 0.6666(2) 0.6025(5) 0.0338(12) Uani 1 1 d . . . . .
N5 N 0.1822(6) 0.7160(2) 0.6878(6) 0.0390(12) Uani 1 1 d . . . . .
C1 C 0.4767(7) 0.4791(3) 0.7564(6) 0.0360(14) Uani 1 1 d . . . . .
C2 C 0.3247(7) 0.5228(3) 0.7874(6) 0.0349(14) Uani 1 1 d . . . . .
C3 C 0.2968(7) 0.6694(3) 0.6730(7) 0.0364(14) Uani 1 1 d . . . . .
C4 C 0.5249(7) 0.7175(3) 0.5409(6) 0.0371(14) Uani 1 1 d . . . . .
C5 C 0.4135(8) 0.7676(3) 0.5511(7) 0.0392(14) Uani 1 1 d . . . . .
H5 H 0.4522 0.8026 0.5074 0.047 Uiso 1 1 calc R U . . .
C6 C 0.2411(7) 0.7647(3) 0.6284(7) 0.0414(16) Uani 1 1 d . . . . .
C7 C 0.4755(9) 0.4184(3) 0.8153(8) 0.0425(16) Uani 1 1 d . . . . .
H7A H 0.5056 0.3914 0.7372 0.064 Uiso 1 1 calc R U . . .
H7B H 0.3464 0.4096 0.8492 0.064 Uiso 1 1 calc R U . . .
H7C H 0.5737 0.4148 0.8977 0.064 Uiso 1 1 calc R U . . .
C8 C 0.1583(7) 0.5069(3) 0.8786(7) 0.0412(15) Uani 1 1 d . . . . .
H8A H 0.0924 0.5421 0.9088 0.062 Uiso 1 1 calc R U . . .
H8B H 0.2083 0.4857 0.9662 0.062 Uiso 1 1 calc R U . . .
H8C H 0.0655 0.4826 0.8205 0.062 Uiso 1 1 calc R U . . .
C9 C 0.7111(8) 0.7168(3) 0.4626(7) 0.0412(15) Uani 1 1 d . . . . .
H9A H 0.8204 0.7070 0.5326 0.062 Uiso 1 1 calc R U . . .
H9B H 0.7329 0.7550 0.4204 0.062 Uiso 1 1 calc R U . . .
H9C H 0.7011 0.6879 0.3838 0.062 Uiso 1 1 calc R U . . .
C10 C 0.1122(8) 0.8177(3) 0.6485(8) 0.0470(17) Uani 1 1 d . . . . .
H10A H -0.0253 0.8066 0.6332 0.070 Uiso 1 1 calc R U . . .
H10B H 0.1425 0.8474 0.5767 0.070 Uiso 1 1 calc R U . . .
H10C H 0.1370 0.8330 0.7483 0.070 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 2.020(4) . ?
Cu1 N1 2.053(5) . ?
Cu1 N4 2.094(5) . ?
Cu1 Cl2 2.2812(16) . ?
Cu1 Cl1 2.4587(16) . ?
O1 N1 1.412(6) . ?
O1 H1 0.899(10) . ?
N1 C1 1.294(7) . ?
N2 C2 1.282(8) . ?
N2 N3 1.361(7) . ?
N3 C3 1.394(7) . ?
N3 H3 0.8800 . ?
N4 C3 1.359(7) . ?
N4 C4 1.380(8) . ?
N5 C6 1.326(8) . ?
N5 C3 1.349(7) . ?
C1 C2 1.495(8) . ?
C1 C7 1.504(9) . ?
C2 C8 1.502(8) . ?
C4 C5 1.396(8) . ?
C4 C9 1.505(8) . ?
C5 C6 1.419(8) . ?
C5 H5 0.9500 . ?
C6 C10 1.531(9) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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
N2 Cu1 N1 76.18(19) . . ?
N2 Cu1 N4 78.93(19) . . ?
N1 Cu1 N4 153.03(16) . . ?
N2 Cu1 Cl2 160.35(16) . . ?
N1 Cu1 Cl2 89.96(13) . . ?
N4 Cu1 Cl2 111.21(14) . . ?
N2 Cu1 Cl1 96.01(15) . . ?
N1 Cu1 Cl1 99.16(14) . . ?
N4 Cu1 Cl1 93.58(13) . . ?
Cl2 Cu1 Cl1 99.95(6) . . ?
N1 O1 H1 108(6) . . ?
C1 N1 O1 115.1(5) . . ?
C1 N1 Cu1 117.9(4) . . ?
O1 N1 Cu1 126.5(3) . . ?
C2 N2 N3 126.1(5) . . ?
C2 N2 Cu1 118.4(4) . . ?
N3 N2 Cu1 115.2(4) . . ?
N2 N3 C3 115.5(5) . . ?
N2 N3 H3 122.2 . . ?
C3 N3 H3 122.2 . . ?
C3 N4 C4 116.0(5) . . ?
C3 N4 Cu1 111.7(4) . . ?
C4 N4 Cu1 131.6(4) . . ?
C6 N5 C3 116.4(5) . . ?
N1 C1 C2 112.2(5) . . ?
N1 C1 C7 124.7(5) . . ?
C2 C1 C7 123.0(5) . . ?
N2 C2 C1 114.3(5) . . ?
N2 C2 C8 125.3(5) . . ?
C1 C2 C8 120.4(5) . . ?
N5 C3 N4 127.2(6) . . ?
N5 C3 N3 114.9(5) . . ?
N4 C3 N3 117.9(5) . . ?
N4 C4 C5 120.2(5) . . ?
N4 C4 C9 118.0(5) . . ?
C5 C4 C9 121.8(6) . . ?
C4 C5 C6 118.3(6) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
N5 C6 C5 121.9(6) . . ?
N5 C6 C10 116.1(5) . . ?
C5 C6 C10 122.0(6) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
C2 N2 N3 C3 -178.5(5) . . . . ?
Cu1 N2 N3 C3 7.8(6) . . . . ?
O1 N1 C1 C2 -179.1(4) . . . . ?
Cu1 N1 C1 C2 8.1(6) . . . . ?
O1 N1 C1 C7 2.6(8) . . . . ?
Cu1 N1 C1 C7 -170.3(5) . . . . ?
N3 N2 C2 C1 179.8(5) . . . . ?
Cu1 N2 C2 C1 -6.6(7) . . . . ?
N3 N2 C2 C8 -1.8(9) . . . . ?
Cu1 N2 C2 C8 171.8(4) . . . . ?
N1 C1 C2 N2 -1.0(7) . . . . ?
C7 C1 C2 N2 177.3(5) . . . . ?
N1 C1 C2 C8 -179.6(5) . . . . ?
C7 C1 C2 C8 -1.2(8) . . . . ?
C6 N5 C3 N4 -0.9(9) . . . . ?
C6 N5 C3 N3 176.0(5) . . . . ?
C4 N4 C3 N5 0.8(8) . . . . ?
Cu1 N4 C3 N5 171.9(5) . . . . ?
C4 N4 C3 N3 -176.0(5) . . . . ?
Cu1 N4 C3 N3 -4.9(6) . . . . ?
N2 N3 C3 N5 -178.9(5) . . . . ?
N2 N3 C3 N4 -1.7(7) . . . . ?
C3 N4 C4 C5 -0.9(8) . . . . ?
Cu1 N4 C4 C5 -169.9(4) . . . . ?
C3 N4 C4 C9 179.5(5) . . . . ?
Cu1 N4 C4 C9 10.5(8) . . . . ?
N4 C4 C5 C6 1.2(8) . . . . ?
C9 C4 C5 C6 -179.2(5) . . . . ?
C3 N5 C6 C5 1.1(8) . . . . ?
C3 N5 C6 C10 -178.8(5) . . . . ?
C4 C5 C6 N5 -1.4(9) . . . . ?
C4 C5 C6 C10 178.5(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
O1 H1 Cl2 0.90(6) 2.44(6) 3.133(5) 134(7) .
N3 H3 Cl1 0.88 2.46 3.312(4) 163.6 1_455

_refine_diff_density_max         1.497
_refine_diff_density_min         -1.437
_refine_diff_density_rms         0.174

_shelxl_version_number           2013-4

