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

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

data_KG144
_database_code_depnum_ccdc_archive 'CCDC 1535654'
_audit_update_record             
;
2017-03-02 deposited with the CCDC.
2017-05-21 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         'C26 H32 Br2 Cl4 Cu3 N4 O4'
_chemical_formula_sum            'C26 H32 Br2 Cl4 Cu3 N4 O4'
_chemical_formula_weight         956.79

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'
Br Br -0.2901 2.4595 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   9.1230(9)
_cell_length_b                   16.1575(15)
_cell_length_c                   21.934(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3233.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    144
_cell_measurement_theta_min      9.30
_cell_measurement_theta_max      20.42

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.966
_exptl_crystal_F_000             1892
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    4.798
_shelx_estimated_absorpt_T_min   0.309
_shelx_estimated_absorpt_T_max   0.620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.421
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30022
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.857
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2926
_reflns_number_gt                2501
_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, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015b)'
_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)+(0.0361P)²+2.9005P] 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         2926
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.0706
_refine_ls_wR_factor_gt          0.0658
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.0000 0.5000 0.5000 0.03183(14) Uani 1 2 d S . P . .
Cu2 Cu 0.29158(4) 0.43075(2) 0.52816(2) 0.03186(11) Uani 1 1 d . . . . .
Br1 Br 0.17842(5) 0.28826(3) 0.20879(2) 0.06933(16) Uani 1 1 d . . . . .
Cl1 Cl 0.26613(9) 0.56738(5) 0.55009(3) 0.03949(19) Uani 1 1 d . . . . .
Cl2 Cl 0.02237(9) 0.39312(5) 0.57089(4) 0.03942(19) Uani 1 1 d . . . . .
O1 O 0.1604(2) 0.44499(12) 0.45699(9) 0.0353(5) Uani 1 1 d . . . . .
O2 O 0.5703(3) 0.45029(17) 0.71305(10) 0.0557(7) Uani 1 1 d . . . . .
N1 N 0.3771(3) 0.33284(15) 0.49093(11) 0.0326(6) Uani 1 1 d . . . . .
N2 N 0.4128(3) 0.39969(15) 0.60336(11) 0.0325(6) Uani 1 1 d . . . . .
C1 C 0.1591(3) 0.40460(17) 0.40393(13) 0.0292(6) Uani 1 1 d . . . . .
C2 C 0.0553(3) 0.42443(19) 0.35938(14) 0.0351(7) Uani 1 1 d . . . . .
H2 H -0.0188 0.4619 0.3686 0.042 Uiso 1 1 calc R U . . .
C3 C 0.0605(3) 0.38951(19) 0.30208(14) 0.0364(7) Uani 1 1 d . . . . .
H3 H -0.0080 0.4041 0.2726 0.044 Uiso 1 1 calc R U . . .
C4 C 0.1686(3) 0.3327(2) 0.28909(13) 0.0370(7) Uani 1 1 d . . . . .
C5 C 0.2676(3) 0.3079(2) 0.33215(14) 0.0380(7) Uani 1 1 d . . . . .
H5 H 0.3373 0.2679 0.3227 0.046 Uiso 1 1 calc R U . . .
C6 C 0.2638(3) 0.34303(18) 0.39105(13) 0.0305(6) Uani 1 1 d . . . . .
C7 C 0.3634(3) 0.30888(19) 0.43563(14) 0.0359(7) Uani 1 1 d . . . . .
H7 H 0.4230 0.2655 0.4230 0.043 Uiso 1 1 calc R U . . .
C8 C 0.4757(4) 0.2876(2) 0.53234(14) 0.0432(8) Uani 1 1 d . . . . .
H8A H 0.5765 0.3047 0.5260 0.052 Uiso 1 1 calc R U . . .
H8B H 0.4688 0.2285 0.5252 0.052 Uiso 1 1 calc R U . . .
C9 C 0.4272(4) 0.30819(19) 0.59634(14) 0.0400(7) Uani 1 1 d . . . . .
H9A H 0.3337 0.2819 0.6047 0.048 Uiso 1 1 calc R U . . .
H9B H 0.4984 0.2872 0.6253 0.048 Uiso 1 1 calc R U . . .
C10 C 0.5569(3) 0.4431(2) 0.60272(14) 0.0388(7) Uani 1 1 d . . . . .
H10A H 0.5403 0.5022 0.5992 0.047 Uiso 1 1 calc R U . . .
H10B H 0.6120 0.4255 0.5672 0.047 Uiso 1 1 calc R U . . .
C11 C 0.6464(4) 0.4263(2) 0.65945(16) 0.0493(9) Uani 1 1 d . . . . .
H11A H 0.6691 0.3677 0.6616 0.059 Uiso 1 1 calc R U . . .
H11B H 0.7382 0.4564 0.6570 0.059 Uiso 1 1 calc R U . . .
C12 C 0.4356(4) 0.4066(3) 0.71709(14) 0.0513(9) Uani 1 1 d . . . . .
H12A H 0.3838 0.4237 0.7536 0.062 Uiso 1 1 calc R U . . .
H12B H 0.4553 0.3478 0.7204 0.062 Uiso 1 1 calc R U . . .
C13 C 0.3398(4) 0.4224(2) 0.66189(14) 0.0418(8) Uani 1 1 d . . . . .
H13A H 0.2499 0.3908 0.6659 0.050 Uiso 1 1 calc R U . . .
H13B H 0.3137 0.4806 0.6607 0.050 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 O1 1.9546(19) 5_566 ?
Cu1 O1 1.9547(19) . ?
Cu1 Cl2 2.3327(8) . ?
Cu1 Cl2 2.3328(8) 5_566 ?
Cu1 Cu2 2.9512(4) . ?
Cu1 Cu2 2.9512(4) 5_566 ?
Cu2 N1 1.944(2) . ?
Cu2 O1 1.980(2) . ?
Cu2 N2 2.048(2) . ?
Cu2 Cl1 2.2713(9) . ?
Cu2 Cl2 2.6982(9) . ?
Br1 C4 1.904(3) . ?
O1 C1 1.334(3) . ?
O2 C11 1.419(4) . ?
O2 C12 1.421(4) . ?
N1 C7 1.279(4) . ?
N1 C8 1.473(4) . ?
N2 C10 1.490(4) . ?
N2 C13 1.492(4) . ?
N2 C9 1.492(4) . ?
C1 C2 1.398(4) . ?
C1 C6 1.408(4) . ?
C2 C3 1.378(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(4) . ?
C5 C6 1.412(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.445(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.509(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.513(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.515(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.0 5_566 . ?
O1 Cu1 Cl2 94.61(6) 5_566 . ?
O1 Cu1 Cl2 85.39(6) . . ?
O1 Cu1 Cl2 85.39(6) 5_566 5_566 ?
O1 Cu1 Cl2 94.61(6) . 5_566 ?
Cl2 Cu1 Cl2 180.0 . 5_566 ?
O1 Cu1 Cu2 138.26(6) 5_566 . ?
O1 Cu1 Cu2 41.75(6) . . ?
Cl2 Cu1 Cu2 60.06(2) . . ?
Cl2 Cu1 Cu2 119.94(2) 5_566 . ?
O1 Cu1 Cu2 41.74(6) 5_566 5_566 ?
O1 Cu1 Cu2 138.26(6) . 5_566 ?
Cl2 Cu1 Cu2 119.94(2) . 5_566 ?
Cl2 Cu1 Cu2 60.06(2) 5_566 5_566 ?
Cu2 Cu1 Cu2 179.999(13) . 5_566 ?
N1 Cu2 O1 90.35(9) . . ?
N1 Cu2 N2 85.53(10) . . ?
O1 Cu2 N2 171.69(9) . . ?
N1 Cu2 Cl1 157.08(8) . . ?
O1 Cu2 Cl1 89.55(6) . . ?
N2 Cu2 Cl1 97.05(7) . . ?
N1 Cu2 Cl2 109.15(8) . . ?
O1 Cu2 Cl2 75.51(7) . . ?
N2 Cu2 Cl2 99.01(7) . . ?
Cl1 Cu2 Cl2 93.00(3) . . ?
N1 Cu2 Cu1 125.63(7) . . ?
O1 Cu2 Cu1 41.08(6) . . ?
N2 Cu2 Cu1 138.42(7) . . ?
Cl1 Cu2 Cu1 65.40(2) . . ?
Cl2 Cu2 Cu1 48.522(18) . . ?
Cu1 Cl2 Cu2 71.41(2) . . ?
C1 O1 Cu1 129.55(19) . . ?
C1 O1 Cu2 129.49(18) . . ?
Cu1 O1 Cu2 97.17(8) . . ?
C11 O2 C12 109.8(3) . . ?
C7 N1 C8 119.6(3) . . ?
C7 N1 Cu2 127.2(2) . . ?
C8 N1 Cu2 112.97(19) . . ?
C10 N2 C13 106.6(2) . . ?
C10 N2 C9 112.8(2) . . ?
C13 N2 C9 111.8(2) . . ?
C10 N2 Cu2 110.69(18) . . ?
C13 N2 Cu2 113.04(18) . . ?
C9 N2 Cu2 101.95(18) . . ?
O1 C1 C2 120.2(3) . . ?
O1 C1 C6 121.0(3) . . ?
C2 C1 C6 118.8(3) . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C4 C3 C2 119.1(3) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C5 C4 C3 121.7(3) . . ?
C5 C4 Br1 119.8(2) . . ?
C3 C4 Br1 118.5(2) . . ?
C4 C5 C6 119.9(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 119.0(3) . . ?
C1 C6 C7 124.1(3) . . ?
C5 C6 C7 116.8(3) . . ?
N1 C7 C6 126.0(3) . . ?
N1 C7 H7 117.0 . . ?
C6 C7 H7 117.0 . . ?
N1 C8 C9 106.6(3) . . ?
N1 C8 H8A 110.4 . . ?
C9 C8 H8A 110.4 . . ?
N1 C8 H8B 110.4 . . ?
C9 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?
N2 C9 C8 109.9(3) . . ?
N2 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
N2 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
N2 C10 C11 112.6(3) . . ?
N2 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
N2 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
O2 C11 C10 111.6(3) . . ?
O2 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
O2 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
O2 C12 C13 111.4(3) . . ?
O2 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
O2 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
N2 C13 C12 112.9(3) . . ?
N2 C13 H13A 109.0 . . ?
C12 C13 H13A 109.0 . . ?
N2 C13 H13B 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?

_refine_diff_density_max         0.764
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_KG20
_database_code_depnum_ccdc_archive 'CCDC 1535653'
_audit_update_record             
;
2017-03-02 deposited with the CCDC.
2017-05-21 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         'C11 H14 Cl Cu N5 O'
_chemical_formula_sum            'C11 H14 Cl Cu N5 O'
_chemical_formula_weight         331.26

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           9
_space_group_name_H-M_alt        'C 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'

_cell_length_a                   13.5037(6)
_cell_length_b                   16.8086(6)
_cell_length_c                   6.7657(3)
_cell_angle_alpha                90
_cell_angle_beta                 119.501(4)
_cell_angle_gamma                90
_cell_volume                     1336.56(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    230
_cell_measurement_theta_min      7.53
_cell_measurement_theta_max      20.62

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_F_000             676
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.833
_shelx_estimated_absorpt_T_min   0.758
_shelx_estimated_absorpt_T_max   0.898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9687
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.114
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2448
_reflns_number_gt                2250
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.992
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.999

_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, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015b)'
_refine_special_details          
'Refined as a 2-component inversion twin., 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)+(0.0290P)²] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.03(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2448
_refine_ls_number_parameters     178
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0294
_refine_ls_wR_factor_ref         0.0629
_refine_ls_wR_factor_gt          0.0615
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.67267(6) 0.46157(3) 0.61306(9) 0.03674(17) Uani 1 1 d . . . . .
Cl1 Cl 0.09748(15) 0.59484(13) 0.0818(3) 0.0848(7) Uani 1 1 d . . . . .
O1 O 0.5874(3) 0.5511(2) 0.4356(7) 0.0462(11) Uani 1 1 d . . . . .
N1 N 0.5450(4) 0.3890(3) 0.4199(8) 0.0395(12) Uani 1 1 d . . . . .
N2 N 0.7796(4) 0.3743(3) 0.8174(9) 0.0404(12) Uani 1 1 d . . . . .
H1 H 0.759(4) 0.377(3) 0.908(9) 0.047(18) Uiso 1 1 d . . . . .
N3 N 0.7609(5) 0.5375(3) 0.8753(8) 0.0411(13) Uani 1 1 d . . . . .
N4 N 0.7933(4) 0.5985(3) 0.8398(7) 0.0431(11) Uani 1 1 d . . . . .
N5 N 0.8253(5) 0.6587(3) 0.8086(9) 0.0663(14) Uani 1 1 d . . . . .
C1 C 0.4766(4) 0.5583(3) 0.3554(8) 0.0380(12) Uani 1 1 d . . . . .
C2 C 0.4265(5) 0.6345(3) 0.3148(8) 0.0448(13) Uani 1 1 d . . . . .
H2 H 0.4726 0.6790 0.3450 0.054 Uiso 1 1 calc R U . . .
C3 C 0.3123(5) 0.6450(3) 0.2325(9) 0.0495(14) Uani 1 1 d . . . . .
H3 H 0.2817 0.6959 0.2083 0.059 Uiso 1 1 calc R U . . .
C4 C 0.2426(5) 0.5790(4) 0.1855(9) 0.0485(16) Uani 1 1 d . . . . .
C5 C 0.2858(4) 0.5045(3) 0.2152(8) 0.0451(12) Uani 1 1 d . . . . .
H5 H 0.2374 0.4608 0.1776 0.054 Uiso 1 1 calc R U . . .
C6 C 0.4025(4) 0.4925(3) 0.3018(8) 0.0355(11) Uani 1 1 d . . . . .
C7 C 0.4433(5) 0.4120(4) 0.3203(9) 0.0411(14) Uani 1 1 d . . . . .
H7 H 0.3881 0.3728 0.2508 0.049 Uiso 1 1 calc R U . . .
C8 C 0.5668(5) 0.3041(3) 0.3977(11) 0.0527(16) Uani 1 1 d . . . . .
H8A H 0.6036 0.2998 0.3060 0.063 Uiso 1 1 calc R U . . .
H8B H 0.4947 0.2762 0.3193 0.063 Uiso 1 1 calc R U . . .
C9 C 0.6405(5) 0.2650(3) 0.6240(11) 0.0584(17) Uani 1 1 d . . . . .
H9A H 0.6090 0.2763 0.7226 0.070 Uiso 1 1 calc R U . . .
H9B H 0.6377 0.2079 0.6019 0.070 Uiso 1 1 calc R U . . .
C10 C 0.7616(5) 0.2909(3) 0.7400(10) 0.0502(16) Uani 1 1 d . . . . .
H10A H 0.8049 0.2567 0.8703 0.060 Uiso 1 1 calc R U . . .
H10B H 0.7913 0.2837 0.6367 0.060 Uiso 1 1 calc R U . . .
C11 C 0.9021(5) 0.3957(4) 0.9219(12) 0.063(2) Uani 1 1 d . . . . .
H11A H 0.9470 0.3569 1.0348 0.095 Uiso 1 1 calc R U . . .
H11B H 0.9143 0.4472 0.9916 0.095 Uiso 1 1 calc R U . . .
H11C H 0.9239 0.3969 0.8067 0.095 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 O1 1.916(4) . ?
Cu1 N1 1.987(5) . ?
Cu1 N3 2.028(5) . ?
Cu1 N2 2.045(5) . ?
Cu1 N3 2.427(5) 2_564 ?
Cl1 C4 1.746(5) . ?
O1 C1 1.322(7) . ?
N1 C7 1.257(7) . ?
N1 C8 1.478(7) . ?
N2 C10 1.474(7) . ?
N2 C11 1.487(8) . ?
N2 H1 0.79(5) . ?
N3 N4 1.186(6) . ?
N3 Cu1 2.427(5) 2_565 ?
N4 N5 1.159(6) . ?
C1 C2 1.410(7) . ?
C1 C6 1.413(7) . ?
C2 C3 1.369(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.355(8) . ?
C5 C6 1.400(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.443(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.506(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.488(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N1 90.65(19) . . ?
O1 Cu1 N3 88.11(19) . . ?
N1 Cu1 N3 155.11(19) . . ?
O1 Cu1 N2 173.4(2) . . ?
N1 Cu1 N2 95.70(17) . . ?
N3 Cu1 N2 86.8(2) . . ?
O1 Cu1 N3 85.35(17) . 2_564 ?
N1 Cu1 N3 96.77(18) . 2_564 ?
N3 Cu1 N3 107.9(2) . 2_564 ?
N2 Cu1 N3 92.24(19) . 2_564 ?
C1 O1 Cu1 122.5(3) . . ?
C7 N1 C8 117.5(5) . . ?
C7 N1 Cu1 121.9(4) . . ?
C8 N1 Cu1 120.5(4) . . ?
C10 N2 C11 110.4(5) . . ?
C10 N2 Cu1 120.3(4) . . ?
C11 N2 Cu1 113.4(4) . . ?
C10 N2 H1 106(4) . . ?
C11 N2 H1 111(4) . . ?
Cu1 N2 H1 95(4) . . ?
N4 N3 Cu1 118.9(4) . . ?
N4 N3 Cu1 118.6(4) . 2_565 ?
Cu1 N3 Cu1 108.4(2) . 2_565 ?
N5 N4 N3 178.8(5) . . ?
O1 C1 C2 120.0(5) . . ?
O1 C1 C6 123.3(5) . . ?
C2 C1 C6 116.7(5) . . ?
C3 C2 C1 122.2(5) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
C2 C3 C4 119.5(5) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 120.8(5) . . ?
C5 C4 Cl1 121.1(5) . . ?
C3 C4 Cl1 118.1(5) . . ?
C4 C5 C6 120.6(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 120.3(5) . . ?
C5 C6 C7 118.3(5) . . ?
C1 C6 C7 121.4(5) . . ?
N1 C7 C6 127.2(6) . . ?
N1 C7 H7 116.4 . . ?
C6 C7 H7 116.4 . . ?
N1 C8 C9 112.5(5) . . ?
N1 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
N1 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C8 114.4(5) . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
N2 C10 C9 114.3(5) . . ?
N2 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
N2 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_refine_diff_density_max         0.257
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.044

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 H1 N5 0.79(7) 2.47(6) 3.117(9) 139(5) 2_565
C3 H3 N5 0.93 2.53 3.331(7) 145.0 4_464

####################################################################### 
# 
# 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_AB119
_database_code_depnum_ccdc_archive 'CCDC 1535655'
_audit_update_record             
;
2017-03-02 deposited with the CCDC.
2017-05-21 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         'C12 H17 Cl2 Cu N3 O'
_chemical_formula_sum            'C12 H17 Cl2 Cu N3 O'
_chemical_formula_weight         353.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   24.123(6)
_cell_length_b                   6.7026(16)
_cell_length_c                   17.890(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2892.6(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    211
_cell_measurement_theta_min      8.25
_cell_measurement_theta_max      17.50

_exptl_crystal_description       block
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_F_000             1448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.874
_shelx_estimated_absorpt_T_min   0.672
_shelx_estimated_absorpt_T_max   0.835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.358
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29647
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.688
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5223
_reflns_number_gt                4611
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.931
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_molecular_graphics    
'ORTEP-3 (Farrugia, 2012) and SCHAKAL (Keller, 1999)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015b)'
_refine_special_details          
'Refined as a 2-component inversion twin., 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)+(0.0936P)²+0.3535P] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.18(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5223
_refine_ls_number_parameters     344
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1337
_refine_ls_wR_factor_gt          0.1267
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.046
_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 0.27838(3) 0.39673(12) 0.12737(5) 0.0276(3) Uani 1 1 d . . . . .
Cu2 Cu 0.46780(3) 0.10679(13) 0.37233(5) 0.0274(3) Uani 1 1 d . . . . .
Cl1 Cl 0.27048(8) 0.6585(3) 0.20609(12) 0.0356(5) Uani 1 1 d . . . . .
Cl2 Cl 0.29653(8) 0.5417(4) 0.00221(14) 0.0403(5) Uani 1 1 d . . . . .
Cl3 Cl 0.47455(8) -0.1532(3) 0.29272(13) 0.0378(5) Uani 1 1 d . . . . .
Cl4 Cl 0.44803(8) -0.0412(3) 0.49624(14) 0.0391(5) Uani 1 1 d . . . . .
O1 O 0.0829(3) 0.4373(12) 0.1647(5) 0.0538(19) Uani 1 1 d . . . . .
O2 O 0.6627(2) 0.0389(12) 0.3368(5) 0.0484(17) Uani 1 1 d . . . . .
N1 N 0.3607(2) 0.3410(10) 0.1489(4) 0.0316(16) Uani 1 1 d . . . . .
N2 N 0.2835(3) 0.1120(10) 0.0977(5) 0.0327(18) Uani 1 1 d . . . . .
N3 N 0.1942(2) 0.3394(9) 0.1135(4) 0.0257(14) Uani 1 1 d . . . . .
N4 N 0.3865(3) 0.1728(10) 0.3493(4) 0.0316(15) Uani 1 1 d . . . . .
N5 N 0.4650(3) 0.3894(10) 0.4035(5) 0.0323(17) Uani 1 1 d . . . . .
N6 N 0.5531(2) 0.1530(10) 0.3878(4) 0.0275(14) Uani 1 1 d . . . . .
C1 C 0.3994(4) 0.4696(16) 0.1732(6) 0.040(2) Uani 1 1 d . . . . .
H1 H 0.3886 0.5964 0.1884 0.048 Uiso 1 1 calc R U . . .
C2 C 0.4542(4) 0.4187(15) 0.1760(6) 0.046(2) Uani 1 1 d . . . . .
H2 H 0.4803 0.5098 0.1934 0.056 Uiso 1 1 calc R U . . .
C3 C 0.4706(4) 0.2323(17) 0.1530(6) 0.052(3) Uani 1 1 d . . . . .
H3 H 0.5079 0.1976 0.1525 0.062 Uiso 1 1 calc R U . . .
C4 C 0.4303(3) 0.0962(13) 0.1305(6) 0.0386(19) Uani 1 1 d . . . . .
H4 H 0.4403 -0.0330 0.1171 0.046 Uiso 1 1 calc R U . . .
C5 C 0.3763(3) 0.1537(12) 0.1282(5) 0.0314(17) Uani 1 1 d . . . . .
C6 C 0.3301(3) 0.0300(14) 0.1028(5) 0.032(2) Uani 1 1 d . . . . .
H6 H 0.3351 -0.1039 0.0909 0.038 Uiso 1 1 calc R U . . .
C7 C 0.2323(3) 0.0160(13) 0.0739(8) 0.041(3) Uani 1 1 d . . . . .
H7A H 0.2175 -0.0657 0.1140 0.049 Uiso 1 1 calc R U . . .
H7B H 0.2390 -0.0686 0.0309 0.049 Uiso 1 1 calc R U . . .
C8 C 0.1918(3) 0.1807(13) 0.0540(5) 0.0342(18) Uani 1 1 d . . . . .
H8A H 0.2014 0.2375 0.0059 0.041 Uiso 1 1 calc R U . . .
H8B H 0.1546 0.1269 0.0507 0.041 Uiso 1 1 calc R U . . .
C9 C 0.1704(3) 0.2722(14) 0.1861(5) 0.0337(19) Uani 1 1 d . . . . .
H9A H 0.1806 0.3676 0.2245 0.040 Uiso 1 1 calc R U . . .
H9B H 0.1868 0.1450 0.1993 0.040 Uiso 1 1 calc R U . . .
C10 C 0.1082(4) 0.2498(16) 0.1861(6) 0.051(3) Uani 1 1 d . . . . .
H10A H 0.0974 0.1461 0.1512 0.061 Uiso 1 1 calc R U . . .
H10B H 0.0956 0.2114 0.2355 0.061 Uiso 1 1 calc R U . . .
C11 C 0.1004(4) 0.4875(15) 0.0907(6) 0.039(3) Uani 1 1 d . . . . .
H11A H 0.0821 0.6090 0.0747 0.047 Uiso 1 1 calc R U . . .
H11B H 0.0901 0.3815 0.0565 0.047 Uiso 1 1 calc R U . . .
C12 C 0.1616(3) 0.5165(11) 0.0889(5) 0.027(2) Uani 1 1 d . . . . .
H12A H 0.1710 0.6285 0.1208 0.033 Uiso 1 1 calc R U . . .
H12B H 0.1725 0.5507 0.0383 0.033 Uiso 1 1 calc R U . . .
C13 C 0.3471(3) 0.0504(16) 0.3252(6) 0.042(2) Uani 1 1 d . . . . .
H13 H 0.3570 -0.0768 0.3092 0.050 Uiso 1 1 calc R U . . .
C14 C 0.2916(4) 0.1064(16) 0.3231(6) 0.050(3) Uani 1 1 d . . . . .
H14 H 0.2645 0.0172 0.3072 0.060 Uiso 1 1 calc R U . . .
C15 C 0.2777(3) 0.2948(16) 0.3450(6) 0.045(2) Uani 1 1 d . . . . .
H15 H 0.2408 0.3349 0.3438 0.054 Uiso 1 1 calc R U . . .
C16 C 0.3179(3) 0.4264(14) 0.3688(5) 0.040(2) Uani 1 1 d . . . . .
H16 H 0.3090 0.5561 0.3828 0.048 Uiso 1 1 calc R U . . .
C17 C 0.3719(3) 0.3583(12) 0.3709(5) 0.0327(17) Uani 1 1 d . . . . .
C18 C 0.4187(3) 0.4805(13) 0.4000(6) 0.034(2) Uani 1 1 d . . . . .
H18 H 0.4144 0.6129 0.4144 0.041 Uiso 1 1 calc R U . . .
C19 C 0.5158(3) 0.4804(13) 0.4292(7) 0.036(2) Uani 1 1 d . . . . .
H19A H 0.5090 0.5602 0.4735 0.044 Uiso 1 1 calc R U . . .
H19B H 0.5314 0.5655 0.3908 0.044 Uiso 1 1 calc R U . . .
C20 C 0.5552(3) 0.3085(12) 0.4471(5) 0.0322(18) Uani 1 1 d . . . . .
H20A H 0.5928 0.3592 0.4513 0.039 Uiso 1 1 calc R U . . .
H20B H 0.5451 0.2497 0.4947 0.039 Uiso 1 1 calc R U . . .
C21 C 0.5772(3) 0.2213(13) 0.3152(5) 0.0361(19) Uani 1 1 d . . . . .
H21A H 0.5630 0.3532 0.3038 0.043 Uiso 1 1 calc R U . . .
H21B H 0.5652 0.1317 0.2759 0.043 Uiso 1 1 calc R U . . .
C22 C 0.6395(3) 0.2286(14) 0.3159(6) 0.044(2) Uani 1 1 d . . . . .
H22A H 0.6528 0.2655 0.2667 0.053 Uiso 1 1 calc R U . . .
H22B H 0.6517 0.3298 0.3510 0.053 Uiso 1 1 calc R U . . .
C23 C 0.6448(4) -0.0104(14) 0.4089(7) 0.045(3) Uani 1 1 d . . . . .
H23A H 0.6563 0.0927 0.4437 0.054 Uiso 1 1 calc R U . . .
H23B H 0.6618 -0.1351 0.4243 0.054 Uiso 1 1 calc R U . . .
C24 C 0.5816(3) -0.0310(13) 0.4103(6) 0.034(2) Uani 1 1 d . . . . .
H24A H 0.5707 -0.1382 0.3769 0.041 Uiso 1 1 calc R U . . .
H24B H 0.5700 -0.0670 0.4604 0.041 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 1.985(7) . ?
Cu1 N1 2.058(6) . ?
Cu1 N3 2.082(6) . ?
Cu1 Cl1 2.258(2) . ?
Cu1 Cl2 2.480(3) . ?
Cu2 N5 1.975(7) . ?
Cu2 N4 2.052(6) . ?
Cu2 N6 2.099(6) . ?
Cu2 Cl3 2.256(2) . ?
Cu2 Cl4 2.475(3) . ?
O1 C11 1.430(12) . ?
O1 C10 1.448(12) . ?
O2 C23 1.400(14) . ?
O2 C22 1.438(11) . ?
N1 C1 1.341(11) . ?
N1 C5 1.362(11) . ?
N2 C6 1.255(11) . ?
N2 C7 1.457(10) . ?
N3 C12 1.490(9) . ?
N3 C9 1.491(11) . ?
N3 C8 1.505(11) . ?
N4 C13 1.327(11) . ?
N4 C17 1.349(11) . ?
N5 C18 1.276(11) . ?
N5 C19 1.445(11) . ?
N6 C24 1.469(10) . ?
N6 C20 1.488(11) . ?
N6 C21 1.493(11) . ?
C1 C2 1.368(13) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(14) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(13) . ?
C3 H3 0.9300 . ?
C4 C5 1.360(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.460(11) . ?
C6 H6 0.9300 . ?
C7 C8 1.516(12) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.507(11) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.488(12) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.393(13) . ?
C13 H13 0.9300 . ?
C14 C15 1.363(15) . ?
C14 H14 0.9300 . ?
C15 C16 1.378(13) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(11) . ?
C16 H16 0.9300 . ?
C17 C18 1.489(12) . ?
C18 H18 0.9300 . ?
C19 C20 1.528(11) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.504(11) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.532(12) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?

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 79.4(3) . . ?
N2 Cu1 N3 81.5(3) . . ?
N1 Cu1 N3 158.5(2) . . ?
N2 Cu1 Cl1 156.8(2) . . ?
N1 Cu1 Cl1 96.1(2) . . ?
N3 Cu1 Cl1 97.79(19) . . ?
N2 Cu1 Cl2 97.1(2) . . ?
N1 Cu1 Cl2 94.0(2) . . ?
N3 Cu1 Cl2 97.85(19) . . ?
Cl1 Cu1 Cl2 105.88(9) . . ?
N5 Cu2 N4 79.5(3) . . ?
N5 Cu2 N6 81.7(3) . . ?
N4 Cu2 N6 158.7(3) . . ?
N5 Cu2 Cl3 157.1(2) . . ?
N4 Cu2 Cl3 96.2(2) . . ?
N6 Cu2 Cl3 97.25(19) . . ?
N5 Cu2 Cl4 97.2(2) . . ?
N4 Cu2 Cl4 94.7(2) . . ?
N6 Cu2 Cl4 97.5(2) . . ?
Cl3 Cu2 Cl4 105.64(9) . . ?
C11 O1 C10 109.0(8) . . ?
C23 O2 C22 109.2(7) . . ?
C1 N1 C5 119.3(7) . . ?
C1 N1 Cu1 127.9(6) . . ?
C5 N1 Cu1 112.5(5) . . ?
C6 N2 C7 126.0(7) . . ?
C6 N2 Cu1 117.2(6) . . ?
C7 N2 Cu1 116.7(5) . . ?
C12 N3 C9 107.1(6) . . ?
C12 N3 C8 109.6(6) . . ?
C9 N3 C8 112.8(6) . . ?
C12 N3 Cu1 113.8(4) . . ?
C9 N3 Cu1 109.1(4) . . ?
C8 N3 Cu1 104.6(4) . . ?
C13 N4 C17 118.4(7) . . ?
C13 N4 Cu2 128.0(6) . . ?
C17 N4 Cu2 113.1(5) . . ?
C18 N5 C19 123.8(8) . . ?
C18 N5 Cu2 118.4(6) . . ?
C19 N5 Cu2 117.8(5) . . ?
C24 N6 C20 112.1(7) . . ?
C24 N6 C21 108.3(7) . . ?
C20 N6 C21 113.0(6) . . ?
C24 N6 Cu2 111.8(5) . . ?
C20 N6 Cu2 103.4(4) . . ?
C21 N6 Cu2 108.2(5) . . ?
N1 C1 C2 121.6(10) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C1 C2 C3 119.6(9) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C4 118.8(8) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 119.5(8) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 N1 121.1(8) . . ?
C4 C5 C6 125.4(8) . . ?
N1 C5 C6 113.5(7) . . ?
N2 C6 C5 117.2(8) . . ?
N2 C6 H6 121.4 . . ?
C5 C6 H6 121.4 . . ?
N2 C7 C8 107.1(7) . . ?
N2 C7 H7A 110.3 . . ?
C8 C7 H7A 110.3 . . ?
N2 C7 H7B 110.3 . . ?
C8 C7 H7B 110.3 . . ?
H7A C7 H7B 108.6 . . ?
N3 C8 C7 108.9(8) . . ?
N3 C8 H8A 109.9 . . ?
C7 C8 H8A 109.9 . . ?
N3 C8 H8B 109.9 . . ?
C7 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
N3 C9 C10 114.4(7) . . ?
N3 C9 H9A 108.7 . . ?
C10 C9 H9A 108.7 . . ?
N3 C9 H9B 108.7 . . ?
C10 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
O1 C10 C9 109.4(7) . . ?
O1 C10 H10A 109.8 . . ?
C9 C10 H10A 109.8 . . ?
O1 C10 H10B 109.8 . . ?
C9 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
O1 C11 C12 110.1(8) . . ?
O1 C11 H11A 109.6 . . ?
C12 C11 H11A 109.6 . . ?
O1 C11 H11B 109.6 . . ?
C12 C11 H11B 109.6 . . ?
H11A C11 H11B 108.2 . . ?
C11 C12 N3 114.4(7) . . ?
C11 C12 H12A 108.7 . . ?
N3 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
N3 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
N4 C13 C14 122.1(10) . . ?
N4 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
C15 C14 C13 118.5(9) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 C16 120.7(8) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C17 117.4(8) . . ?
C15 C16 H16 121.3 . . ?
C17 C16 H16 121.3 . . ?
N4 C17 C16 123.0(8) . . ?
N4 C17 C18 114.1(7) . . ?
C16 C17 C18 122.9(8) . . ?
N5 C18 C17 114.7(8) . . ?
N5 C18 H18 122.6 . . ?
C17 C18 H18 122.6 . . ?
N5 C19 C20 106.0(7) . . ?
N5 C19 H19A 110.5 . . ?
C20 C19 H19A 110.5 . . ?
N5 C19 H19B 110.5 . . ?
C20 C19 H19B 110.5 . . ?
H19A C19 H19B 108.7 . . ?
N6 C20 C19 111.0(7) . . ?
N6 C20 H20A 109.4 . . ?
C19 C20 H20A 109.4 . . ?
N6 C20 H20B 109.4 . . ?
C19 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
N6 C21 C22 113.1(7) . . ?
N6 C21 H21A 109.0 . . ?
C22 C21 H21A 109.0 . . ?
N6 C21 H21B 109.0 . . ?
C22 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
O2 C22 C21 111.2(7) . . ?
O2 C22 H22A 109.4 . . ?
C21 C22 H22A 109.4 . . ?
O2 C22 H22B 109.4 . . ?
C21 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
O2 C23 C24 110.0(9) . . ?
O2 C23 H23A 109.7 . . ?
C24 C23 H23A 109.7 . . ?
O2 C23 H23B 109.7 . . ?
C24 C23 H23B 109.7 . . ?
H23A C23 H23B 108.2 . . ?
N6 C24 C23 112.7(7) . . ?
N6 C24 H24A 109.0 . . ?
C23 C24 H24A 109.0 . . ?
N6 C24 H24B 109.0 . . ?
C23 C24 H24B 109.0 . . ?
H24A C24 H24B 107.8 . . ?

_refine_diff_density_max         3.118
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.126

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
C2 H2 O1 0.93 2.55 3.257(12) 133 3_565
C7 H7A Cl1 0.97 2.79 3.490(12) 130 1_545
C11 H11A Cl4 0.97 2.83 3.768(10) 164 4_564
C14 H14 O2 0.93 2.54 3.268(11) 135 3_455
C24 H24A Cl3 0.97 2.77 3.430(9) 126 1_555

