# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_inicCuClb
_database_code_depnum_ccdc_archive 'CCDC 1884643'
loop_
_audit_author_name
_audit_author_address
'Melanie Rademeyer'
;University of Pretoria
South Africa
;
_audit_update_record             
;
2018-12-12 deposited with the CCDC.	2019-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 Cl2 Cu N4 O2'
_chemical_formula_sum            'C12 H12 Cl2 Cu N4 O2'
_chemical_formula_weight         378.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   3.7235(2)
_cell_length_b                   23.3797(10)
_cell_length_c                   7.9055(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.548(4)
_cell_angle_gamma                90
_cell_volume                     683.72(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6114
_cell_measurement_theta_max      31.1290
_cell_measurement_theta_min      3.1330

_exptl_crystal_description       'thick needle'
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.839
_exptl_crystal_F_000             617
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.075
_exptl_crystal_size_mid          0.017
_exptl_crystal_size_min          0.013
_exptl_absorpt_coefficient_mu    1.996
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.23a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2607
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.742
_diffrn_reflns_theta_max         31.076
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.782
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.782
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.782
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             2607
_reflns_number_gt                2425
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_cell_refinement       'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0623P)²+0.2566P] 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         2607
_refine_ls_number_parameters     98
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0915
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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 0.500000 0.500000 1.000000 0.01472(13) Uani 1 2 d S . P . .
Cl1 Cl 0.07891(14) 0.55062(2) 0.82513(6) 0.01475(14) Uani 1 1 d . . . . .
O1 O 0.3824(5) 0.24983(7) 0.50744(19) 0.0221(4) Uani 1 1 d . . . . .
N1 N 0.4599(5) 0.43459(7) 0.8325(2) 0.0142(3) Uani 1 1 d . . . . .
N2 N 0.1538(6) 0.31427(7) 0.3091(2) 0.0189(4) Uani 1 1 d . . . . .
H2A H 0.113701 0.288715 0.230981 0.023 Uiso 1 1 calc R U . . .
H2B H 0.100587 0.349465 0.286727 0.023 Uiso 1 1 calc R U . . .
C1 C 0.5169(6) 0.44388(8) 0.6695(2) 0.0144(4) Uani 1 1 d . . . . .
H1 H 0.590519 0.480026 0.638508 0.017 Uiso 1 1 calc R U . . .
C2 C 0.4697(5) 0.40147(8) 0.5463(3) 0.0136(4) Uani 1 1 d . . . . .
H2 H 0.511350 0.409068 0.434729 0.016 Uiso 1 1 calc R U . . .
C5 C 0.3637(6) 0.38180(8) 0.8774(2) 0.0152(4) Uani 1 1 d . . . . .
H5 H 0.332174 0.374876 0.990577 0.018 Uiso 1 1 calc R U . . .
C4 C 0.3098(6) 0.33735(8) 0.7616(2) 0.0144(4) Uani 1 1 d . . . . .
H4 H 0.241823 0.301337 0.796521 0.017 Uiso 1 1 calc R U . . .
C3 C 0.3588(5) 0.34735(8) 0.5924(2) 0.0123(4) Uani 1 1 d . . . . .
C6 C 0.2988(6) 0.29928(8) 0.4653(2) 0.0146(4) 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
Cu1 N1 2.0174(17) 3_667 ?
Cu1 N1 2.0174(17) . ?
Cu1 Cl1 2.2968(5) 3_667 ?
Cu1 Cl1 2.2969(5) . ?
O1 C6 1.233(3) . ?
N1 C5 1.344(3) . ?
N1 C1 1.347(2) . ?
N2 C6 1.337(3) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C1 C2 1.387(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.392(3) . ?
C2 H2 0.9300 . ?
C5 C4 1.384(3) . ?
C5 H5 0.9300 . ?
C4 C3 1.391(3) . ?
C4 H4 0.9300 . ?
C3 C6 1.507(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
N1 Cu1 N1 180.0 3_667 . ?
N1 Cu1 Cl1 90.06(5) 3_667 3_667 ?
N1 Cu1 Cl1 89.94(5) . 3_667 ?
N1 Cu1 Cl1 89.94(5) 3_667 . ?
N1 Cu1 Cl1 90.06(5) . . ?
Cl1 Cu1 Cl1 180.0 3_667 . ?
C5 N1 C1 118.45(17) . . ?
C5 N1 Cu1 121.65(13) . . ?
C1 N1 Cu1 119.85(13) . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N1 C1 C2 122.37(18) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C1 C2 C3 118.92(18) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
N1 C5 C4 122.54(18) . . ?
N1 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C5 C4 C3 118.99(18) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C3 C2 118.67(17) . . ?
C4 C3 C6 119.34(17) . . ?
C2 C3 C6 121.97(17) . . ?
O1 C6 N2 123.92(19) . . ?
O1 C6 C3 120.36(18) . . ?
N2 C6 C3 115.71(17) . . ?

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
C5 N1 C1 C2 1.9(3) . . . . ?
Cu1 N1 C1 C2 -175.63(16) . . . . ?
N1 C1 C2 C3 0.1(3) . . . . ?
C1 N1 C5 C4 -2.2(3) . . . . ?
Cu1 N1 C5 C4 175.32(17) . . . . ?
N1 C5 C4 C3 0.4(3) . . . . ?
C5 C4 C3 C2 1.6(3) . . . . ?
C5 C4 C3 C6 -179.7(2) . . . . ?
C1 C2 C3 C4 -1.9(3) . . . . ?
C1 C2 C3 C6 179.46(19) . . . . ?
C4 C3 C6 O1 -36.0(3) . . . . ?
C2 C3 C6 O1 142.6(2) . . . . ?
C4 C3 C6 N2 144.2(2) . . . . ?
C2 C3 C6 N2 -37.2(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
_geom_hbond_publ_flag
N2 H2A O1 0.86 2.08 2.899(2) 158.7 4_565 yes
N2 H2B Cl1 0.86 2.56 3.4126(18) 171.6 3_566 yes
C1 H1 Cl1 0.93 2.76 3.396(2) 126.8 1_655 yes
C2 H2 Cl1 0.93 2.86 3.719(2) 155.0 3_666 yes
C5 H5 Cl1 0.93 2.83 3.410(2) 121.6 3_567 yes
C4 H4 O1 0.93 2.55 3.342(3) 143.0 4_566 yes

_refine_diff_density_max         0.811
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.091

####################################################################### 
# 
# 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_inicCuCla
_database_code_depnum_ccdc_archive 'CCDC 1884644'
loop_
_audit_author_name
_audit_author_address
'Melanie Rademeyer'
;University of Pretoria
South Africa
;
_audit_update_record             
;
2018-12-12 deposited with the CCDC.	2019-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 Cl2 Cu N4 O2'
_chemical_formula_sum            'C12 H12 Cl2 Cu N4 O2'
_chemical_formula_weight         378.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+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                   24.171(4)
_cell_length_b                   3.7103(5)
_cell_length_c                   32.824(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.493(5)
_cell_angle_gamma                90
_cell_volume                     2739.0(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      26.26

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.837
_exptl_crystal_F_000             1528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.993
_shelx_estimated_absorpt_T_min   0.741
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6802
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33282
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_av_R_equivalents  0.0856
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         2.147
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2809
_reflns_number_gt                2490
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXTS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL, SHELXL-2014/7 (Sheldrick, 2015)'
_computing_publication_material  
;
 ORTEP-3 for Windows (Farrugia, 1997), POV-RAY (Cason, 2004),
 Mercury (Macrae et al., 2008)
;
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0784P)²+68.4533P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0005(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2809
_refine_ls_number_parameters     132
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.1843
_refine_ls_wR_factor_gt          0.1799
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.097
_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 0.49665(3) 0.4054(2) 0.37168(2) 0.0094(3) Uani 1 1 d . . . . .
Cl2 Cl 0.55602(7) 0.0561(4) 0.34675(5) 0.0113(4) Uani 1 1 d . . . . .
Cl1 Cl 0.44361(7) 0.8296(4) 0.39421(5) 0.0094(4) Uani 1 1 d . . . . .
O1 O 0.7355(2) 0.8046(16) 0.56288(15) 0.0208(12) Uani 1 1 d . . . . .
O2 O 0.2488(2) 0.6347(15) 0.17990(16) 0.0203(12) Uani 1 1 d . . . . .
N3 N 0.4320(3) 0.4154(16) 0.31148(18) 0.0133(4) Uani 1 1 d . . . . .
N4 N 0.3125(3) 0.4281(16) 0.14910(18) 0.0133(4) Uani 1 1 d . . . . .
H4A H 0.286695 0.457576 0.122261 0.016 Uiso 1 1 calc R U . . .
H4B H 0.348153 0.342219 0.153440 0.016 Uiso 1 1 calc R U . . .
N1 N 0.5615(3) 0.4265(16) 0.43157(18) 0.0133(4) Uani 1 1 d . . . . .
N2 N 0.6772(3) 0.5597(16) 0.59526(18) 0.0133(4) Uani 1 1 d . . . . .
H2A H 0.701725 0.621344 0.621584 0.016 Uiso 1 1 calc R U . . .
H2B H 0.644198 0.443063 0.592042 0.016 Uiso 1 1 calc R U . . .
C10 C 0.3303(3) 0.3588(18) 0.26278(19) 0.0120(14) Uani 1 1 d D . . . .
H10 H 0.290346 0.302534 0.258880 0.014 Uiso 1 1 calc R U . . .
C11 C 0.3751(3) 0.3345(18) 0.3039(2) 0.0109(13) Uani 1 1 d D . . . .
H11 H 0.364806 0.257013 0.327830 0.013 Uiso 1 1 calc R U . . .
C7 C 0.4458(3) 0.520(2) 0.2772(2) 0.0133(4) Uani 1 1 d D . . . .
H7 H 0.486014 0.577525 0.282008 0.016 Uiso 1 1 calc R U . . .
C8 C 0.4039(3) 0.5481(18) 0.2352(2) 0.0122(13) Uani 1 1 d D . . . .
H8 H 0.415550 0.622570 0.211826 0.015 Uiso 1 1 calc R U . . .
C9 C 0.3449(3) 0.4669(17) 0.2274(2) 0.0098(13) Uani 1 1 d D . . . .
C12 C 0.2976(3) 0.513(2) 0.1831(2) 0.0144(14) Uani 1 1 d . . . . .
C2 C 0.5889(3) 0.4044(19) 0.5097(2) 0.0133(4) Uani 1 1 d D . . . .
H2 H 0.578295 0.348300 0.534180 0.016 Uiso 1 1 calc R U . . .
C1 C 0.5483(3) 0.3507(19) 0.4673(2) 0.0133(4) Uani 1 1 d D . . . .
H1 H 0.510102 0.257526 0.463343 0.016 Uiso 1 1 calc R U . . .
C5 C 0.6162(3) 0.541(2) 0.4381(2) 0.0133(4) Uani 1 1 d D . . . .
H5 H 0.626563 0.581269 0.413166 0.016 Uiso 1 1 calc R U . . .
C4 C 0.6591(3) 0.6046(19) 0.47917(19) 0.0133(4) Uani 1 1 d D . . . .
H4 H 0.697395 0.690121 0.482041 0.016 Uiso 1 1 calc R U . . .
C3 C 0.6452(3) 0.5416(19) 0.5161(2) 0.0133(4) Uani 1 1 d D . . . .
C6 C 0.6901(3) 0.6426(19) 0.5604(2) 0.0133(4) 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
Cu1 N1 2.017(6) . ?
Cu1 N3 2.021(6) . ?
Cu1 Cl2 2.2954(18) . ?
Cu1 Cl1 2.3157(17) . ?
Cu1 Cl1 2.7294(18) 1_545 ?
O1 C6 1.226(9) . ?
O2 C12 1.232(9) . ?
N3 C11 1.341(9) . ?
N3 C7 1.342(8) . ?
N4 C12 1.329(9) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N1 C5 1.331(9) . ?
N1 C1 1.353(8) . ?
N2 C6 1.328(9) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
C10 C11 1.390(8) . ?
C10 C9 1.392(8) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C7 C8 1.383(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.386(8) . ?
C8 H8 0.9500 . ?
C9 C12 1.494(9) . ?
C2 C1 1.393(8) . ?
C2 C3 1.397(8) . ?
C2 H2 0.9500 . ?
C1 H1 0.9500 . ?
C5 C4 1.387(8) . ?
C5 H5 0.9500 . ?
C4 C3 1.389(8) . ?
C4 H4 0.9500 . ?
C3 C6 1.510(9) . ?

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 N3 176.7(3) . . ?
N1 Cu1 Cl2 90.31(17) . . ?
N3 Cu1 Cl2 91.25(17) . . ?
N1 Cu1 Cl1 89.18(17) . . ?
N3 Cu1 Cl1 88.86(17) . . ?
Cl2 Cu1 Cl1 171.56(7) . . ?
N1 Cu1 Cl1 92.32(18) . 1_545 ?
N3 Cu1 Cl1 90.45(18) . 1_545 ?
Cl2 Cu1 Cl1 94.11(6) . 1_545 ?
Cl1 Cu1 Cl1 94.33(6) . 1_545 ?
Cu1 Cl1 Cu1 94.33(6) . 1_565 ?
C11 N3 C7 117.6(6) . . ?
C11 N3 Cu1 123.4(4) . . ?
C7 N3 Cu1 119.0(5) . . ?
C12 N4 H4A 120.0 . . ?
C12 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C5 N1 C1 117.6(6) . . ?
C5 N1 Cu1 122.7(4) . . ?
C1 N1 Cu1 119.5(5) . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C11 C10 C9 119.0(6) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N3 C11 C10 123.1(6) . . ?
N3 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
N3 C7 C8 122.8(6) . . ?
N3 C7 H7 118.6 . . ?
C8 C7 H7 118.6 . . ?
C7 C8 C9 119.7(6) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C10 117.8(6) . . ?
C8 C9 C12 121.6(6) . . ?
C10 C9 C12 120.5(6) . . ?
O2 C12 N4 124.2(6) . . ?
O2 C12 C9 119.5(6) . . ?
N4 C12 C9 116.3(6) . . ?
C1 C2 C3 119.4(6) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
N1 C1 C2 122.3(6) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
N1 C5 C4 123.7(6) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
C5 C4 C3 119.1(6) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C3 C2 117.7(6) . . ?
C4 C3 C6 118.7(6) . . ?
C2 C3 C6 123.4(6) . . ?
O1 C6 N2 122.9(6) . . ?
O1 C6 C3 119.7(6) . . ?
N2 C6 C3 117.4(6) . . ?

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
C7 N3 C11 C10 -0.8(10) . . . . ?
Cu1 N3 C11 C10 176.8(5) . . . . ?
C9 C10 C11 N3 1.0(10) . . . . ?
C11 N3 C7 C8 0.2(10) . . . . ?
Cu1 N3 C7 C8 -177.4(5) . . . . ?
N3 C7 C8 C9 0.2(11) . . . . ?
C7 C8 C9 C10 0.0(10) . . . . ?
C7 C8 C9 C12 176.5(6) . . . . ?
C11 C10 C9 C8 -0.5(10) . . . . ?
C11 C10 C9 C12 -177.1(6) . . . . ?
C8 C9 C12 O2 -139.9(7) . . . . ?
C10 C9 C12 O2 36.5(10) . . . . ?
C8 C9 C12 N4 38.1(10) . . . . ?
C10 C9 C12 N4 -145.5(7) . . . . ?
C5 N1 C1 C2 3.0(10) . . . . ?
Cu1 N1 C1 C2 -171.6(5) . . . . ?
C3 C2 C1 N1 0.1(11) . . . . ?
C1 N1 C5 C4 -3.6(11) . . . . ?
Cu1 N1 C5 C4 170.8(6) . . . . ?
N1 C5 C4 C3 1.1(11) . . . . ?
C5 C4 C3 C2 2.1(11) . . . . ?
C5 C4 C3 C6 -174.6(7) . . . . ?
C1 C2 C3 C4 -2.6(11) . . . . ?
C1 C2 C3 C6 174.0(7) . . . . ?
C4 C3 C6 O1 6.1(11) . . . . ?
C2 C3 C6 O1 -170.5(7) . . . . ?
C4 C3 C6 N2 -176.1(7) . . . . ?
C2 C3 C6 N2 7.4(11) . . . . ?

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
_geom_hbond_publ_flag
N4 H4A O1 0.88 2.08 2.932(7) 161.7 8_465 yes
N4 H4B Cl2 0.88 2.55 3.421(6) 170.7 2_655 yes
N2 H2A O2 0.88 2.04 2.911(8) 167.8 8_566 yes
N2 H2B Cl1 0.88 2.54 3.388(6) 163.0 5_666 yes
C10 H10 O2 0.95 2.59 3.244(8) 126.2 4_545 yes
C11 H11 Cl1 0.95 2.80 3.382(6) 120.3 1_545 yes
C7 H7 Cl2 0.95 2.81 3.436(7) 124.3 1_565 yes
C8 H8 Cl2 0.95 2.78 3.693(7) 161.5 2_665 yes
C2 H2 Cl1 0.95 2.67 3.623(7) 175.9 5_666 yes
C1 H1 Cl1 0.95 2.75 3.384(7) 124.6 1_545 yes
C5 H5 Cl2 0.95 2.84 3.400(7) 119.1 1_565 yes
C4 H4 O1 0.95 2.56 3.330(8) 138.2 7_666 yes
N4 H4A O1 0.88 2.08 2.932(7) 161.7 8_465 yes
N4 H4B Cl2 0.88 2.55 3.421(6) 170.7 2_655 yes
N2 H2A O2 0.88 2.04 2.911(8) 167.8 8_566 yes
N2 H2B Cl1 0.88 2.54 3.388(6) 163.0 5_666 yes
C10 H10 O2 0.95 2.59 3.244(8) 126.2 4_545 yes
C11 H11 Cl1 0.95 2.80 3.382(6) 120.3 1_545 yes
C7 H7 Cl2 0.95 2.81 3.436(7) 124.3 1_565 yes
C8 H8 Cl2 0.95 2.78 3.693(7) 161.5 2_665 yes
C2 H2 Cl1 0.95 2.67 3.623(7) 175.9 5_666 yes
C1 H1 Cl1 0.95 2.75 3.384(7) 124.6 1_545 yes
C5 H5 Cl2 0.95 2.84 3.400(7) 119.1 1_565 yes
C4 H4 O1 0.95 2.56 3.330(8) 138.2 7_666 yes

_refine_diff_density_max         1.339
_refine_diff_density_min         -1.052
_refine_diff_density_rms         0.176

####################################################################### 
# 
# 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_inicCuBra
_database_code_depnum_ccdc_archive 'CCDC 1884646'
loop_
_audit_author_name
_audit_author_address
'Melanie Rademeyer'
;University of Pretoria
South Africa
;
_audit_update_record             
;
2018-12-12 deposited with the CCDC.	2019-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 Br2 Cu N4 O2'
_chemical_formula_sum            'C12 H12 Br2 Cu N4 O2'
_chemical_formula_weight         467.62

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'
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'
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'
H H 0.0000 0.0000 '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                   3.8846(7)
_cell_length_b                   23.760(5)
_cell_length_c                   7.9582(13)
_cell_angle_alpha                90
_cell_angle_beta                 96.190(16)
_cell_angle_gamma                90
_cell_volume                     730.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9645
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      27.13

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.127
_exptl_crystal_F_000             454
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.308
_exptl_crystal_size_mid          0.029
_exptl_crystal_size_min          0.023
_exptl_absorpt_coefficient_mu    6.975
_shelx_estimated_absorpt_T_min   0.223
_shelx_estimated_absorpt_T_max   0.856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.655500
_exptl_absorpt_correction_T_max  0.862048
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6275
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.713
_diffrn_reflns_theta_max         27.229
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1603
_reflns_number_gt                1423
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXTS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXTL, SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
 ORTEP-3 for Windows (Farrugia, 1997), POV-RAY (Cason, 2004),
 Mercury (Macrae et al., 2008)
;
_computing_publication_material  'SHELXL-2014, PLATON (Spek, 2009)'

_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)+(0.0137P)²+3.5169P]
 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         1603
_refine_ls_number_parameters     121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.0779
_refine_ls_wR_factor_gt          0.0750
_refine_ls_goodness_of_fit_ref   1.200
_refine_ls_restrained_S_all      1.200
_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
Br1 Br 1.07383(12) -0.05108(2) 0.31035(5) 0.01279(14) Uani 1 1 d . . . . .
Cu1 Cu 0.5000 0.0000 0.5000 0.0139(2) Uani 1 2 d S . P . .
O1 O 0.4017(10) 0.25081(13) 0.0301(4) 0.0245(8) Uani 1 1 d . . . . .
N1 N 0.4623(10) 0.06606(15) 0.3391(5) 0.0123(8) Uani 1 1 d . . . . .
N2 N 0.1737(12) 0.18934(18) -0.1681(5) 0.0201(10) Uani 1 1 d . . . . .
C5 C 0.3735(13) 0.11784(18) 0.3895(6) 0.0146(10) Uani 1 1 d . . . . .
C4 C 0.3228(12) 0.16284(18) 0.2785(6) 0.0130(9) Uani 1 1 d . . . . .
C3 C 0.3694(12) 0.15456(17) 0.1091(5) 0.0109(9) Uani 1 1 d . . . . .
C2 C 0.4760(12) 0.10165(18) 0.0581(6) 0.0143(9) Uani 1 1 d . . . . .
C1 C 0.5164(12) 0.05907(18) 0.1766(5) 0.0139(10) Uani 1 1 d . . . . .
C6 C 0.3158(13) 0.20276(18) -0.0144(6) 0.0146(10) Uani 1 1 d . . . . .
H5 H 0.336(12) 0.1230(19) 0.505(6) 0.007(11) Uiso 1 1 d . . . . .
H4 H 0.265(15) 0.201(2) 0.323(7) 0.028(15) Uiso 1 1 d . . . . .
H1 H 0.583(12) 0.025(2) 0.140(6) 0.007(12) Uiso 1 1 d . . . . .
H2 H 0.517(13) 0.090(2) -0.058(6) 0.013(12) Uiso 1 1 d . . . . .
H2A H 0.104(14) 0.217(2) -0.245(7) 0.022(14) Uiso 1 1 d . . . . .
H2B H 0.124(15) 0.158(3) -0.188(7) 0.023(15) 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
Br1 Cu1 2.4398(6) 1_655 ?
Cu1 N1 2.021(4) 3_656 ?
Cu1 N1 2.021(4) . ?
Cu1 Br1 2.4398(6) 1_455 ?
Cu1 Br1 2.4398(6) 3_756 ?
O1 C6 1.231(5) . ?
N1 C1 1.343(6) . ?
N1 C5 1.350(6) . ?
N2 C6 1.326(6) . ?
N2 H2A 0.92(6) . ?
N2 H2B 0.79(6) . ?
C5 C4 1.387(6) . ?
C5 H5 0.95(5) . ?
C4 C3 1.394(6) . ?
C4 H4 1.01(6) . ?
C3 C2 1.397(6) . ?
C3 C6 1.509(6) . ?
C2 C1 1.380(6) . ?
C2 H2 0.99(5) . ?
C1 H1 0.91(5) . ?

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 180.0 3_656 . ?
N1 Cu1 Br1 90.20(11) 3_656 1_455 ?
N1 Cu1 Br1 89.80(11) . 1_455 ?
N1 Cu1 Br1 89.80(11) 3_656 3_756 ?
N1 Cu1 Br1 90.20(11) . 3_756 ?
Br1 Cu1 Br1 180.00(2) 1_455 3_756 ?
C1 N1 C5 118.0(4) . . ?
C1 N1 Cu1 120.4(3) . . ?
C5 N1 Cu1 121.5(3) . . ?
C6 N2 H2A 121(3) . . ?
C6 N2 H2B 119(4) . . ?
H2A N2 H2B 120(5) . . ?
N1 C5 C4 122.5(4) . . ?
N1 C5 H5 118(3) . . ?
C4 C5 H5 119(3) . . ?
C5 C4 C3 118.9(4) . . ?
C5 C4 H4 119(3) . . ?
C3 C4 H4 122(3) . . ?
C4 C3 C2 118.8(4) . . ?
C4 C3 C6 120.0(4) . . ?
C2 C3 C6 121.2(4) . . ?
C1 C2 C3 118.5(4) . . ?
C1 C2 H2 115(3) . . ?
C3 C2 H2 127(3) . . ?
N1 C1 C2 123.3(4) . . ?
N1 C1 H1 120(3) . . ?
C2 C1 H1 117(3) . . ?
O1 C6 N2 124.1(4) . . ?
O1 C6 C3 120.2(4) . . ?
N2 C6 C3 115.6(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
C1 N1 C5 C4 2.8(7) . . . . ?
Cu1 N1 C5 C4 -175.4(4) . . . . ?
N1 C5 C4 C3 -0.8(7) . . . . ?
C5 C4 C3 C2 -2.0(7) . . . . ?
C5 C4 C3 C6 180.0(4) . . . . ?
C4 C3 C2 C1 2.7(7) . . . . ?
C6 C3 C2 C1 -179.2(4) . . . . ?
C5 N1 C1 C2 -1.9(7) . . . . ?
Cu1 N1 C1 C2 176.3(4) . . . . ?
C3 C2 C1 N1 -0.8(7) . . . . ?
C4 C3 C6 O1 36.6(7) . . . . ?
C2 C3 C6 O1 -141.4(5) . . . . ?
C4 C3 C6 N2 -143.3(5) . . . . ?
C2 C3 C6 N2 38.7(7) . . . . ?

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
C5 H5 Br1 0.95(5) 2.85(5) 3.484(5) 125(3) 3_656
C4 H4 O1 1.01(6) 2.55(6) 3.405(6) 142(4) 4_566
N2 H2A O1 0.92(6) 2.02(6) 2.891(5) 157(5) 4_565
N2 H2B Br1 0.79(6) 2.79(6) 3.572(4) 171(5) 3_655
C5 H5 Br1 0.95(5) 2.85(5) 3.484(5) 125(3) 3_656
C4 H4 O1 1.01(6) 2.55(6) 3.405(6) 142(4) 4_566
N2 H2A O1 0.92(6) 2.02(6) 2.891(5) 157(5) 4_565
N2 H2B Br1 0.79(6) 2.79(6) 3.572(4) 171(5) 3_655

_refine_diff_density_max         0.875
_refine_diff_density_min         -0.823
_refine_diff_density_rms         0.160

_shelxl_version_number           2013-2

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_pyrCuBr
_database_code_depnum_ccdc_archive 'CCDC 1884649'
loop_
_audit_author_name
_audit_author_address
'Melanie Rademeyer'
;University of Pretoria
South Africa
;
_audit_update_record             
;
2018-12-12 deposited with the CCDC.	2019-02-20 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 H10 Br2 Cu N6 O2'
_chemical_formula_sum            'C10 H10 Br2 Cu N6 O2'
_chemical_formula_weight         469.60

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'
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      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                   3.7970(7)
_cell_length_b                   6.8449(14)
_cell_length_c                   13.710(3)
_cell_angle_alpha                104.357(6)
_cell_angle_beta                 90.019(8)
_cell_angle_gamma                92.757(6)
_cell_volume                     344.76(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6376
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      27.15

_exptl_crystal_description       needle
_exptl_crystal_colour            bronze
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.262
_exptl_crystal_F_000             227
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.312
_exptl_crystal_size_mid          0.028
_exptl_crystal_size_min          0.027
_exptl_absorpt_coefficient_mu    7.392
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.647569
_exptl_absorpt_correction_T_max  0.837164
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2935
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.068
_diffrn_reflns_theta_max         27.145
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2935
_reflns_number_gt                2553
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXTS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  
;
 ORTEP-3 for Windows (Farrugia, 1997), POV-RAY (Cason, 2004),
 Mercury (Macrae et al., 2008)
;
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0229P)²+1.2777P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2935
_refine_ls_number_parameters     104
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0709
_refine_ls_wR_factor_gt          0.0668
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
Br1 Br 0.91033(14) 0.73144(7) 0.44794(4) 0.01314(14) Uani 1 1 d . . . . .
Cu1 Cu 0.5000 0.5000 0.5000 0.0124(2) Uani 1 2 d S . P . .
O1 O 0.0952(11) 0.5439(5) 0.1312(2) 0.0230(9) Uani 1 1 d . . . . .
N1 N 0.4822(11) 0.3200(5) 0.3564(3) 0.0117(8) Uani 1 1 d . . . . .
N2 N 0.4491(12) 0.0872(6) 0.1569(3) 0.0145(9) Uani 1 1 d . . . . .
N3 N 0.2224(15) 0.2673(8) 0.0091(3) 0.0226(11) Uani 1 1 d . . . . .
C4 C 0.3870(14) 0.3979(7) 0.2809(4) 0.0132(10) Uani 1 1 d . . . . .
H4 H 0.3362 0.5365 0.2947 0.016 Uiso 1 1 calc R U . . .
C3 C 0.3606(13) 0.2811(7) 0.1827(4) 0.0123(10) Uani 1 1 d . . . . .
C2 C 0.5469(15) 0.0118(8) 0.2330(4) 0.0190(11) Uani 1 1 d . . . . .
H2 H 0.6123 -0.1245 0.2187 0.023 Uiso 1 1 calc R U . . .
C1 C 0.5568(14) 0.1248(7) 0.3325(3) 0.0137(10) Uani 1 1 d . . . . .
H1 H 0.6175 0.0624 0.3845 0.016 Uiso 1 1 calc R U . . .
C5 C 0.2170(14) 0.3748(8) 0.1037(4) 0.0148(11) Uani 1 1 d . . . . .
H3A H 0.133(16) 0.319(8) -0.033(4) 0.018 Uiso 1 1 d . U . . .
H3B H 0.298(16) 0.151(9) -0.010(4) 0.018 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Cu1 2.4022(6) . ?
Cu1 N1 2.046(4) . ?
Cu1 N1 2.046(4) 2_666 ?
Cu1 Br1 2.4022(6) 2_666 ?
O1 C5 1.237(6) . ?
N1 C4 1.334(6) . ?
N1 C1 1.339(6) . ?
N2 C2 1.335(6) . ?
N2 C3 1.345(6) . ?
N3 C5 1.324(7) . ?
N3 H3A 0.82(6) . ?
N3 H3B 0.84(6) . ?
C4 C3 1.385(7) . ?
C4 H4 0.9500 . ?
C3 C5 1.503(7) . ?
C2 C1 1.391(7) . ?
C2 H2 0.9500 . ?
C1 H1 0.9500 . ?

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 180.0 . 2_666 ?
N1 Cu1 Br1 90.02(11) . 2_666 ?
N1 Cu1 Br1 89.98(11) 2_666 2_666 ?
N1 Cu1 Br1 89.98(11) . . ?
N1 Cu1 Br1 90.02(11) 2_666 . ?
Br1 Cu1 Br1 180.0 2_666 . ?
C4 N1 C1 116.8(4) . . ?
C4 N1 Cu1 119.2(3) . . ?
C1 N1 Cu1 124.0(3) . . ?
C2 N2 C3 115.4(4) . . ?
C5 N3 H3A 116(4) . . ?
C5 N3 H3B 125(4) . . ?
H3A N3 H3B 119(5) . . ?
N1 C4 C3 121.5(4) . . ?
N1 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
N2 C3 C4 122.4(4) . . ?
N2 C3 C5 119.5(4) . . ?
C4 C3 C5 118.1(4) . . ?
N2 C2 C1 122.6(5) . . ?
N2 C2 H2 118.7 . . ?
C1 C2 H2 118.7 . . ?
N1 C1 C2 121.1(4) . . ?
N1 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
O1 C5 N3 124.4(5) . . ?
O1 C5 C3 118.3(4) . . ?
N3 C5 C3 117.2(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
C1 N1 C4 C3 1.1(7) . . . . ?
Cu1 N1 C4 C3 -178.1(4) . . . . ?
C2 N2 C3 C4 3.3(7) . . . . ?
C2 N2 C3 C5 -174.8(5) . . . . ?
N1 C4 C3 N2 -4.1(8) . . . . ?
N1 C4 C3 C5 174.0(5) . . . . ?
C3 N2 C2 C1 0.1(8) . . . . ?
C4 N1 C1 C2 2.2(7) . . . . ?
Cu1 N1 C1 C2 -178.6(4) . . . . ?
N2 C2 C1 N1 -3.0(8) . . . . ?
N2 C3 C5 O1 170.8(5) . . . . ?
C4 C3 C5 O1 -7.3(7) . . . . ?
N2 C3 C5 N3 -7.6(7) . . . . ?
C4 C3 C5 N3 174.2(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
C4 H4 Br1 0.95 2.76 3.397(5) 125.0 1_455
C1 H1 Br1 0.95 2.89 3.744(5) 150.3 1_545
C1 H1 Br1 0.95 2.94 3.529(5) 121.6 2_766
N3 H3A O1 0.82(6) 2.04(6) 2.864(6) 178(5) 2_565
N3 H3B N2 0.84(6) 2.48(6) 3.190(6) 143(5) 2_655

_refine_diff_density_max         0.625
_refine_diff_density_min         -0.852
_refine_diff_density_rms         0.144

_shelxl_version_number           2013-2

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_inicCuBrb
_database_code_depnum_ccdc_archive 'CCDC 1884645'
loop_
_audit_author_name
_audit_author_address
'Melanie Rademeyer'
;University of Pretoria
South Africa
;
_audit_update_record             
;
2018-12-12 deposited with the CCDC.	2019-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 Br2 Cu N4 O2'
_chemical_formula_sum            'C12 H12 Br2 Cu N4 O2'
_chemical_formula_weight         467.62

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'
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'
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'
H H 0.0000 0.0000 '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                   3.8846(7)
_cell_length_b                   23.760(5)
_cell_length_c                   7.9582(13)
_cell_angle_alpha                90
_cell_angle_beta                 96.190(16)
_cell_angle_gamma                90
_cell_volume                     730.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9645
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      27.13

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.127
_exptl_crystal_F_000             454
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.308
_exptl_crystal_size_mid          0.029
_exptl_crystal_size_min          0.023
_exptl_absorpt_coefficient_mu    6.975
_shelx_estimated_absorpt_T_min   0.223
_shelx_estimated_absorpt_T_max   0.856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.655500
_exptl_absorpt_correction_T_max  0.862048
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6275
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.713
_diffrn_reflns_theta_max         27.229
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1603
_reflns_number_gt                1423
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXTS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXTL, SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
 ORTEP-3 for Windows (Farrugia, 1997), POV-RAY (Cason, 2004),
 Mercury (Macrae et al., 2008)
;
_computing_publication_material  'SHELXL-2014, PLATON (Spek, 2009)'

_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)+(0.0137P)²+3.5169P]
 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         1603
_refine_ls_number_parameters     121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.0779
_refine_ls_wR_factor_gt          0.0750
_refine_ls_goodness_of_fit_ref   1.200
_refine_ls_restrained_S_all      1.200
_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
Br1 Br 1.07383(12) -0.05108(2) 0.31035(5) 0.01279(14) Uani 1 1 d . . . . .
Cu1 Cu 0.5000 0.0000 0.5000 0.0139(2) Uani 1 2 d S . P . .
O1 O 0.4017(10) 0.25081(13) 0.0301(4) 0.0245(8) Uani 1 1 d . . . . .
N1 N 0.4623(10) 0.06606(15) 0.3391(5) 0.0123(8) Uani 1 1 d . . . . .
N2 N 0.1737(12) 0.18934(18) -0.1681(5) 0.0201(10) Uani 1 1 d . . . . .
C5 C 0.3735(13) 0.11784(18) 0.3895(6) 0.0146(10) Uani 1 1 d . . . . .
C4 C 0.3228(12) 0.16284(18) 0.2785(6) 0.0130(9) Uani 1 1 d . . . . .
C3 C 0.3694(12) 0.15456(17) 0.1091(5) 0.0109(9) Uani 1 1 d . . . . .
C2 C 0.4760(12) 0.10165(18) 0.0581(6) 0.0143(9) Uani 1 1 d . . . . .
C1 C 0.5164(12) 0.05907(18) 0.1766(5) 0.0139(10) Uani 1 1 d . . . . .
C6 C 0.3158(13) 0.20276(18) -0.0144(6) 0.0146(10) Uani 1 1 d . . . . .
H5 H 0.336(12) 0.1230(19) 0.505(6) 0.007(11) Uiso 1 1 d . . . . .
H4 H 0.265(15) 0.201(2) 0.323(7) 0.028(15) Uiso 1 1 d . . . . .
H1 H 0.583(12) 0.025(2) 0.140(6) 0.007(12) Uiso 1 1 d . . . . .
H2 H 0.517(13) 0.090(2) -0.058(6) 0.013(12) Uiso 1 1 d . . . . .
H2A H 0.104(14) 0.217(2) -0.245(7) 0.022(14) Uiso 1 1 d . . . . .
H2B H 0.124(15) 0.158(3) -0.188(7) 0.023(15) 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
Br1 Cu1 2.4398(6) 1_655 ?
Cu1 N1 2.021(4) 3_656 ?
Cu1 N1 2.021(4) . ?
Cu1 Br1 2.4398(6) 1_455 ?
Cu1 Br1 2.4398(6) 3_756 ?
O1 C6 1.231(5) . ?
N1 C1 1.343(6) . ?
N1 C5 1.350(6) . ?
N2 C6 1.326(6) . ?
N2 H2A 0.92(6) . ?
N2 H2B 0.79(6) . ?
C5 C4 1.387(6) . ?
C5 H5 0.95(5) . ?
C4 C3 1.394(6) . ?
C4 H4 1.01(6) . ?
C3 C2 1.397(6) . ?
C3 C6 1.509(6) . ?
C2 C1 1.380(6) . ?
C2 H2 0.99(5) . ?
C1 H1 0.91(5) . ?

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 180.0 3_656 . ?
N1 Cu1 Br1 90.20(11) 3_656 1_455 ?
N1 Cu1 Br1 89.80(11) . 1_455 ?
N1 Cu1 Br1 89.80(11) 3_656 3_756 ?
N1 Cu1 Br1 90.20(11) . 3_756 ?
Br1 Cu1 Br1 180.00(2) 1_455 3_756 ?
C1 N1 C5 118.0(4) . . ?
C1 N1 Cu1 120.4(3) . . ?
C5 N1 Cu1 121.5(3) . . ?
C6 N2 H2A 121(3) . . ?
C6 N2 H2B 119(4) . . ?
H2A N2 H2B 120(5) . . ?
N1 C5 C4 122.5(4) . . ?
N1 C5 H5 118(3) . . ?
C4 C5 H5 119(3) . . ?
C5 C4 C3 118.9(4) . . ?
C5 C4 H4 119(3) . . ?
C3 C4 H4 122(3) . . ?
C4 C3 C2 118.8(4) . . ?
C4 C3 C6 120.0(4) . . ?
C2 C3 C6 121.2(4) . . ?
C1 C2 C3 118.5(4) . . ?
C1 C2 H2 115(3) . . ?
C3 C2 H2 127(3) . . ?
N1 C1 C2 123.3(4) . . ?
N1 C1 H1 120(3) . . ?
C2 C1 H1 117(3) . . ?
O1 C6 N2 124.1(4) . . ?
O1 C6 C3 120.2(4) . . ?
N2 C6 C3 115.6(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
C1 N1 C5 C4 2.8(7) . . . . ?
Cu1 N1 C5 C4 -175.4(4) . . . . ?
N1 C5 C4 C3 -0.8(7) . . . . ?
C5 C4 C3 C2 -2.0(7) . . . . ?
C5 C4 C3 C6 180.0(4) . . . . ?
C4 C3 C2 C1 2.7(7) . . . . ?
C6 C3 C2 C1 -179.2(4) . . . . ?
C5 N1 C1 C2 -1.9(7) . . . . ?
Cu1 N1 C1 C2 176.3(4) . . . . ?
C3 C2 C1 N1 -0.8(7) . . . . ?
C4 C3 C6 O1 36.6(7) . . . . ?
C2 C3 C6 O1 -141.4(5) . . . . ?
C4 C3 C6 N2 -143.3(5) . . . . ?
C2 C3 C6 N2 38.7(7) . . . . ?

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
C5 H5 Br1 0.95(5) 2.85(5) 3.484(5) 125(3) 3_656
C4 H4 O1 1.01(6) 2.55(6) 3.405(6) 142(4) 4_566
N2 H2A O1 0.92(6) 2.02(6) 2.891(5) 157(5) 4_565
N2 H2B Br1 0.79(6) 2.79(6) 3.572(4) 171(5) 3_655
C5 H5 Br1 0.95(5) 2.85(5) 3.484(5) 125(3) 3_656
C4 H4 O1 1.01(6) 2.55(6) 3.405(6) 142(4) 4_566
N2 H2A O1 0.92(6) 2.02(6) 2.891(5) 157(5) 4_565
N2 H2B Br1 0.79(6) 2.79(6) 3.572(4) 171(5) 3_655

_refine_diff_density_max         0.875
_refine_diff_density_min         -0.823
_refine_diff_density_rms         0.160

_shelxl_version_number           2013-2

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_pyrCuCl
_database_code_depnum_ccdc_archive 'CCDC 1884648'
loop_
_audit_author_name
_audit_author_address
'Melanie Rademeyer'
;University of Pretoria
South Africa
;
_audit_update_record             
;
2018-12-12 deposited with the CCDC.	2019-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 Cl2 Cu N6 O2'
_chemical_formula_sum            'C10 H10 Cl2 Cu N6 O2'
_chemical_formula_weight         380.69

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'
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'

_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                   3.6610(4)
_cell_length_b                   6.6260(7)
_cell_length_c                   13.7328(15)
_cell_angle_alpha                76.315(3)
_cell_angle_beta                 89.743(3)
_cell_angle_gamma                85.572(3)
_cell_volume                     322.67(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5528
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      28.61

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.959
_exptl_crystal_F_000             191
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    2.120
_shelx_estimated_absorpt_T_min   0.442
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8011
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10015
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.054
_diffrn_reflns_theta_max         28.635
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1628
_reflns_number_gt                1409
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXTS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXTL, SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
ORTEP-3 for Windows (Farrugia, 1997), POV-RAY (Cason, 2004),
 Mercury (Macrae et al., 2008)
;
_computing_publication_material  'SHELXL-2014, PLATON (Spek, 2009)'

_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)+(0.0716P)²+0.4447P]
 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         1628
_refine_ls_number_parameters     117
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1140
_refine_ls_wR_factor_gt          0.1097
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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 0.5000 0.5000 0.5000 0.01088(18) Uani 1 2 d S . P . .
Cl1 Cl 0.08147(18) 0.72398(10) 0.55016(5) 0.01241(19) Uani 1 1 d . . . . .
O1 O 0.0812(6) 0.4542(3) 0.13274(16) 0.0173(5) Uani 1 1 d . . . . .
N1 N 0.4770(6) 0.6866(4) 0.35844(17) 0.0104(5) Uani 1 1 d . . . . .
N2 N 0.4520(7) 0.9204(4) 0.15989(18) 0.0123(5) Uani 1 1 d . . . . .
N3 N 0.2210(8) 0.7334(5) 0.01172(19) 0.0179(6) Uani 1 1 d . . . . .
C3 C 0.3550(7) 0.7234(4) 0.1852(2) 0.0099(5) Uani 1 1 d . . . . .
C2 C 0.5524(8) 0.9995(4) 0.2363(2) 0.0131(6) Uani 1 1 d . . . . .
C1 C 0.5576(8) 0.8868(4) 0.3353(2) 0.0125(5) Uani 1 1 d . . . . .
C4 C 0.3758(8) 0.6043(4) 0.2831(2) 0.0104(5) Uani 1 1 d . . . . .
C5 C 0.2115(8) 0.6250(4) 0.1062(2) 0.0117(5) Uani 1 1 d . . . . .
H4 H 0.328(10) 0.462(6) 0.298(3) 0.016(9) Uiso 1 1 d . . . . .
H1 H 0.604(11) 0.951(6) 0.386(3) 0.021(10) Uiso 1 1 d . . . . .
H2 H 0.628(13) 1.131(8) 0.224(3) 0.038(12) Uiso 1 1 d . . . . .
H3A H 0.151(11) 0.684(6) -0.028(3) 0.014(9) Uiso 1 1 d . . . . .
H3B H 0.323(13) 0.826(8) 0.001(3) 0.034(13) 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 N1 2.040(2) . ?
Cu1 N1 2.040(2) 2_666 ?
Cu1 Cl1 2.2689(7) 2_666 ?
Cu1 Cl1 2.2689(7) . ?
O1 C5 1.236(3) . ?
N1 C4 1.344(4) . ?
N1 C1 1.345(4) . ?
N2 C2 1.343(4) . ?
N2 C3 1.344(4) . ?
N3 C5 1.328(4) . ?
N3 H3A 0.75(4) . ?
N3 H3B 0.73(5) . ?
C3 C4 1.388(4) . ?
C3 C5 1.507(4) . ?
C2 C1 1.388(4) . ?
C2 H2 0.91(5) . ?
C1 H1 0.92(4) . ?
C4 H4 0.95(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
N1 Cu1 N1 180.0 . 2_666 ?
N1 Cu1 Cl1 90.01(7) . 2_666 ?
N1 Cu1 Cl1 89.99(7) 2_666 2_666 ?
N1 Cu1 Cl1 89.99(7) . . ?
N1 Cu1 Cl1 90.01(7) 2_666 . ?
Cl1 Cu1 Cl1 180.0 2_666 . ?
C4 N1 C1 117.7(2) . . ?
C4 N1 Cu1 118.04(18) . . ?
C1 N1 Cu1 124.30(19) . . ?
C2 N2 C3 115.7(2) . . ?
C5 N3 H3A 117(3) . . ?
C5 N3 H3B 118(4) . . ?
H3A N3 H3B 124(5) . . ?
N2 C3 C4 122.5(3) . . ?
N2 C3 C5 120.1(2) . . ?
C4 C3 C5 117.5(2) . . ?
N2 C2 C1 122.8(3) . . ?
N2 C2 H2 120(3) . . ?
C1 C2 H2 117(3) . . ?
N1 C1 C2 120.5(3) . . ?
N1 C1 H1 119(3) . . ?
C2 C1 H1 120(3) . . ?
N1 C4 C3 120.7(2) . . ?
N1 C4 H4 118(2) . . ?
C3 C4 H4 121(2) . . ?
O1 C5 N3 124.1(3) . . ?
O1 C5 C3 118.8(2) . . ?
N3 C5 C3 117.0(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
C2 N2 C3 C4 -3.4(4) . . . . ?
C2 N2 C3 C5 175.5(3) . . . . ?
C3 N2 C2 C1 0.1(4) . . . . ?
C4 N1 C1 C2 -3.0(4) . . . . ?
Cu1 N1 C1 C2 176.8(2) . . . . ?
N2 C2 C1 N1 3.2(5) . . . . ?
C1 N1 C4 C3 -0.2(4) . . . . ?
Cu1 N1 C4 C3 180.0(2) . . . . ?
N2 C3 C4 N1 3.6(4) . . . . ?
C5 C3 C4 N1 -175.4(2) . . . . ?
N2 C3 C5 O1 -171.0(3) . . . . ?
C4 C3 C5 O1 8.0(4) . . . . ?
N2 C3 C5 N3 6.4(4) . . . . ?
C4 C3 C5 N3 -174.6(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
C4 H4 Cl1 0.95(4) 2.67(4) 3.309(3) 125(3) 2_566
C1 H1 Cl1 0.92(4) 2.90(4) 3.431(3) 118(3) 1_655
C1 H1 Cl1 0.92(4) 2.84(4) 3.651(3) 149(3) 2_676
N3 H3A O1 0.75(4) 2.10(4) 2.847(4) 176(4) 2_565
N3 H3B N2 0.73(5) 2.61(5) 3.177(4) 136(4) 2_675

_refine_diff_density_max         2.406
_refine_diff_density_min         -0.643
_refine_diff_density_rms         0.136

_shelxl_version_number           2013-2

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_nicCuBr
_database_code_depnum_ccdc_archive 'CCDC 1884647'
loop_
_audit_author_name
_audit_author_address
'Melanie Rademeyer'
;University of Pretoria
South Africa
;
_audit_update_record             
;
2018-12-12 deposited with the CCDC.	2019-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 Br2 Cu N4 O2'
_chemical_formula_sum            'C12 H12 Br2 Cu N4 O2'
_chemical_formula_weight         467.62

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'

_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                   3.9119(7)
_cell_length_b                   13.828(2)
_cell_length_c                   13.500(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.883(9)
_cell_angle_gamma                90
_cell_volume                     730.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9879
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      27.33

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.127
_exptl_crystal_F_000             454
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.039
_exptl_crystal_size_min          0.036
_exptl_absorpt_coefficient_mu    6.976
_shelx_estimated_absorpt_T_min   0.259
_shelx_estimated_absorpt_T_max   0.787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.502039
_exptl_absorpt_correction_T_max  0.745508
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1590
_diffrn_reflns_av_unetI/netI     0.1154
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.946
_diffrn_reflns_theta_max         27.442
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             1590
_reflns_number_gt                1150
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXTS (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXTL, SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    
;
 ORTEP-3 for Windows (Farrugia, 1997), POV-RAY (Cason, 2004),
 Mercury (Macrae et al., 2008)
;
_computing_publication_material  'SHELXL-2014, PLATON (Spek, 2009)'

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0779P)²]
 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         1590
_refine_ls_number_parameters     98
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1148
_refine_ls_R_factor_gt           0.0692
_refine_ls_wR_factor_ref         0.1445
_refine_ls_wR_factor_gt          0.1306
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_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
Br1 Br 0.1013(4) 0.41899(5) 0.38526(7) 0.0175(3) Uani 1 1 d . . . . .
Cu1 Cu 0.5000 0.5000 0.5000 0.0175(6) Uani 1 2 d S . P . .
N1 N 0.515(3) 0.3809(5) 0.5860(5) 0.019(3) Uani 1 1 d . . . . .
N2 N 0.935(3) 0.0562(4) 0.6216(5) 0.023(2) Uani 1 1 d . . . . .
H2A H 1.0165 0.0023 0.5964 0.028 Uiso 1 1 calc R U . . .
H2B H 0.9501 0.0665 0.6859 0.028 Uiso 1 1 calc R U . . .
C5 C 0.617(4) 0.2954(6) 0.5503(6) 0.018(3) Uani 1 1 d . . . . .
H5 H 0.6561 0.2901 0.4812 0.022 Uiso 1 1 calc R U . . .
C3 C 0.590(4) 0.2219(6) 0.7097(6) 0.021(3) Uani 1 1 d . . . . .
H3 H 0.6147 0.1676 0.7523 0.026 Uiso 1 1 calc R U . . .
C1 C 0.452(3) 0.3875(6) 0.6838(6) 0.015(3) Uani 1 1 d . . . . .
H1 H 0.3891 0.4485 0.7104 0.017 Uiso 1 1 calc R U . . .
C4 C 0.670(3) 0.2135(6) 0.6094(6) 0.013(2) Uani 1 1 d . . . . .
C2 C 0.475(3) 0.3089(6) 0.7468(6) 0.018(3) Uani 1 1 d . . . . .
H2 H 0.4136 0.3146 0.8143 0.021 Uiso 1 1 calc R U . . .
C6 C 0.788(3) 0.1229(6) 0.5618(7) 0.017(3) Uani 1 1 d . . . . .
O1 O 0.761(2) 0.1124(4) 0.4715(5) 0.030(3) 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 2.4521(12) . ?
Cu1 N1 2.015(6) . ?
Cu1 N1 2.015(6) 3_666 ?
Cu1 Br1 2.4521(12) 3_666 ?
N1 C5 1.342(10) . ?
N1 C1 1.349(11) . ?
N2 C6 1.350(13) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
C5 C4 1.399(11) . ?
C5 H5 0.9500 . ?
C3 C2 1.381(12) . ?
C3 C4 1.399(12) . ?
C3 H3 0.9500 . ?
C1 C2 1.382(11) . ?
C1 H1 0.9500 . ?
C4 C6 1.485(12) . ?
C2 H2 0.9500 . ?
C6 O1 1.230(11) . ?

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 180.0 . 3_666 ?
N1 Cu1 Br1 89.8(3) . 3_666 ?
N1 Cu1 Br1 90.2(3) 3_666 3_666 ?
N1 Cu1 Br1 90.2(3) . . ?
N1 Cu1 Br1 89.8(3) 3_666 . ?
Br1 Cu1 Br1 180.0 3_666 . ?
C5 N1 C1 118.1(7) . . ?
C5 N1 Cu1 121.3(6) . . ?
C1 N1 Cu1 120.3(5) . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N1 C5 C4 123.5(7) . . ?
N1 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
C2 C3 C4 120.1(7) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
N1 C1 C2 122.5(8) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C5 C4 C3 116.8(8) . . ?
C5 C4 C6 118.7(7) . . ?
C3 C4 C6 124.4(7) . . ?
C3 C2 C1 118.8(8) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
O1 C6 N2 122.9(9) . . ?
O1 C6 C4 120.4(9) . . ?
N2 C6 C4 116.7(8) . . ?

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
C1 N1 C5 C4 -2(2) . . . . ?
Cu1 N1 C5 C4 172.2(11) . . . . ?
C5 N1 C1 C2 -3(2) . . . . ?
Cu1 N1 C1 C2 -176.7(10) . . . . ?
N1 C5 C4 C3 4(2) . . . . ?
N1 C5 C4 C6 -179.3(12) . . . . ?
C2 C3 C4 C5 -2.1(18) . . . . ?
C2 C3 C4 C6 -178.6(13) . . . . ?
C4 C3 C2 C1 -2.0(19) . . . . ?
N1 C1 C2 C3 5(2) . . . . ?
C5 C4 C6 O1 -17(2) . . . . ?
C3 C4 C6 O1 159.0(13) . . . . ?
C5 C4 C6 N2 160.2(11) . . . . ?
C3 C4 C6 N2 -23.3(19) . . . . ?

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
N2 H2A O1 0.88 2.04 2.911(10) 173.4 3_756
N2 H2B Br1 0.88 2.75 3.624(8) 170.0 4_666
C5 H5 Br1 0.95 2.82 3.406(11) 120.8 1_655
C1 H1 Br1 0.95 2.94 3.556(11) 123.9 3_566

_refine_diff_density_max         1.543
_refine_diff_density_min         -1.651
_refine_diff_density_rms         0.324

_shelxl_version_number           2013-2

