# 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 2018

####################################################################### 
# 
# 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_iran_a425_2
_database_code_depnum_ccdc_archive 'CCDC 1481782'
_audit_update_record             
;
2018-01-29 deposited with the CCDC.
2018-08-20 downloaded from the CCDC.
;
_audit_creation_date             2018-01-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 Cu N6 O6, C H Cl3'
_chemical_formula_sum            'C13 H11 Cl3 Cu N6 O6'
_chemical_formula_weight         517.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H11 Cl3 Cu N6 O6'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.5429(4)
_cell_length_b                   11.9046(6)
_cell_length_c                   17.3544(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.285(5)
_cell_angle_gamma                90
_cell_volume                     1959.68(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2141
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.0490
_cell_measurement_theta_min      3.9250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.568
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_correction_T_min  0.770
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1036
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -6 -22 0.1115
13 -4 0 0.1013
4 5 21 0.0717
-13 3 -1 0.0958
11 -10 0 0.1117
9 11 -10 0.0799
-12 8 1 0.0891
10 11 1 0.0346
0 1 -24 0.1000
0 -1 24 0.0820
-5 -12 16 0.0865
-6 -15 2 0.0714
-4 -15 -5 0.0739

_exptl_crystal_size_max          0.238
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.135
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.0040 -5.9974 -22.0006 0.2630 0.9640 -0.0085
13.0024 -3.9980 -0.0082 -0.0132 -0.1503 0.9897
4.0042 4.9979 20.9993 -0.2484 -0.9438 0.1687
-13.0025 2.9983 -0.9920 0.0649 0.1978 -0.9719
11.0020 -9.9975 -0.0084 0.3656 -0.0825 0.9440
8.9999 11.0004 -10.0029 -0.8461 0.2103 0.4805
-12.0020 7.9975 1.0085 -0.2279 0.0689 -0.9846
10.0020 10.9995 0.9967 -0.8067 -0.2514 0.5330
-0.0040 1.0020 -24.0003 -0.1833 0.9709 0.0246
0.0040 -1.0020 24.0003 0.1833 -0.9709 -0.0246
-4.9982 -12.0004 16.0006 0.8605 -0.5025 -0.1898
-6.0007 -14.9988 2.0002 0.9762 0.1017 -0.1890
-4.0015 -14.9980 -5.0011 0.9022 0.3595 -0.0348

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6347
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.081
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0667
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  77.00   1.00   45.26    --   20.07  19.00 -60.00  103
  2  ω    -10.00  55.00   1.00   45.26    --   20.07 -99.00  90.00   65
  3  ω    -17.00   9.00   1.00   45.26    --  -22.02 -99.00-150.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0185301000
_diffrn_orient_matrix_UB_12      -0.0569691000
_diffrn_orient_matrix_UB_13      0.0052638000
_diffrn_orient_matrix_UB_21      -0.0136601000
_diffrn_orient_matrix_UB_22      -0.0067450000
_diffrn_orient_matrix_UB_23      -0.0407328000
_diffrn_orient_matrix_UB_31      0.0711684000
_diffrn_orient_matrix_UB_32      -0.0160990000
_diffrn_orient_matrix_UB_33      -0.0017071000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2712
_reflns_number_total             3944
_reflns_odcompleteness_completeness 98.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3944
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      0.967
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0440P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1050
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C0AA(H0AA), C4(H4), C1AA(H1AA), C2AA(H2AA), C7(H7), C8(H8), C9(H9), C11(H11),
 C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.41629(4) 0.05532(3) 0.08389(2) 0.03317(15) Uani 1 1 d . . . . .
O1 O 0.5894(3) -0.0796(2) 0.18120(15) 0.0504(7) Uani 1 1 d . . . . .
O2 O 0.7282(3) -0.1633(3) 0.10900(17) 0.0674(9) Uani 1 1 d . . . . .
O3 O 0.5684(2) -0.0520(2) 0.05820(13) 0.0343(6) Uani 1 1 d . . . . .
O4 O 0.2582(2) 0.1688(2) 0.08358(14) 0.0399(6) Uani 1 1 d . . . . .
O5 O 0.3138(3) 0.1196(3) 0.20197(15) 0.0538(8) Uani 1 1 d . . . . .
O6 O 0.1377(3) 0.2321(3) 0.17255(17) 0.0677(9) Uani 1 1 d . . . . .
N1 N -0.0318(3) -0.4046(3) 0.09812(19) 0.0473(8) Uani 1 1 d . . . . .
N2 N 0.2733(3) -0.0670(2) 0.07594(16) 0.0304(7) Uani 1 1 d . . . . .
N3 N 0.5566(3) 0.1783(2) 0.09917(16) 0.0317(7) Uani 1 1 d . . . . .
N4 N 0.8600(3) 0.5175(3) 0.07685(19) 0.0470(8) Uani 1 1 d . . . . .
N3AA N 0.6313(3) -0.1007(3) 0.11842(19) 0.0373(7) Uani 1 1 d . . . . .
N4AA N 0.2356(3) 0.1749(3) 0.1548(2) 0.0426(8) Uani 1 1 d . . . . .
C0AA C -0.0322(3) -0.3267(3) 0.0493(2) 0.0402(9) Uani 1 1 d . . . . .
H0AA H -0.099250 -0.326207 0.006199 0.048 Uiso 1 1 calc R . . . .
C3 C 0.0727(3) -0.2364(3) 0.0603(2) 0.0319(8) Uani 1 1 d . . . . .
C4 C 0.0785(3) -0.1551(3) 0.0043(2) 0.0380(9) Uani 1 1 d . . . . .
H4 H 0.014583 -0.156335 -0.040209 0.046 Uiso 1 1 calc R . . . .
C1AA C 0.1784(3) -0.0724(3) 0.0142(2) 0.0367(9) Uani 1 1 d . . . . .
H1AA H 0.179785 -0.017670 -0.023944 0.044 Uiso 1 1 calc R . . . .
C2AA C 0.2672(3) -0.1449(3) 0.1304(2) 0.0368(9) Uani 1 1 d . . . . .
H2AA H 0.332244 -0.141531 0.174367 0.044 Uiso 1 1 calc R . . . .
C7 C 0.1701(3) -0.2297(3) 0.1249(2) 0.0379(9) Uani 1 1 d . . . . .
H7 H 0.169628 -0.282419 0.164445 0.045 Uiso 1 1 calc R . . . .
C8 C 0.5567(3) 0.2602(3) 0.0473(2) 0.0385(9) Uani 1 1 d . . . . .
H8 H 0.487839 0.259400 0.005028 0.046 Uiso 1 1 calc R . . . .
C9 C 0.6532(4) 0.3458(3) 0.0529(2) 0.0405(9) Uani 1 1 d . . . . .
H9 H 0.649528 0.401362 0.015085 0.049 Uiso 1 1 calc R . . . .
C10 C 0.7559(3) 0.3484(3) 0.1155(2) 0.0336(8) Uani 1 1 d . . . . .
C11 C 0.7540(4) 0.2651(3) 0.1703(2) 0.0469(10) Uani 1 1 d . . . . .
H11 H 0.820316 0.264622 0.213734 0.056 Uiso 1 1 calc R . . . .
C12 C 0.6534(4) 0.1833(3) 0.1601(2) 0.0439(10) Uani 1 1 d . . . . .
H12 H 0.652748 0.127960 0.197916 0.053 Uiso 1 1 calc R . . . .
C13 C 0.8626(4) 0.4379(3) 0.1256(2) 0.0413(9) Uani 1 1 d . . . . .
H13 H 0.931866 0.436067 0.167633 0.050 Uiso 1 1 calc R . . . .
Cl1 Cl -0.05543(13) 0.11443(12) 0.34904(8) 0.0797(4) Uani 1 1 d . . . . .
Cl2 Cl 0.16894(17) -0.04292(15) 0.36150(11) 0.1228(7) Uani 1 1 d . . . . .
Cl3 Cl -0.03151(17) -0.03608(17) 0.22538(11) 0.1291(7) Uani 1 1 d . . . . .
C1 C 0.0604(5) 0.0406(4) 0.2992(3) 0.0665(13) Uani 1 1 d . . . . .
H1 H 0.119879 0.094906 0.275478 0.080 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O3 2.020(2) . ?
Cu1 O4 2.025(2) . ?
Cu1 N2 1.990(2) . ?
Cu1 N3 1.982(2) . ?
O1 N3AA 1.227(4) . ?
O2 N3AA 1.213(4) . ?
O3 N3AA 1.285(3) . ?
O4 N4AA 1.280(4) . ?
O5 N4AA 1.235(4) . ?
O6 N4AA 1.222(3) . ?
N1 N4 1.407(4) 1_445 ?
N1 C0AA 1.255(4) . ?
N2 C1AA 1.327(4) . ?
N2 C2AA 1.330(4) . ?
N3 C8 1.327(4) . ?
N3 C12 1.327(4) . ?
N4 C13 1.269(4) . ?
C0AA H0AA 0.9300 . ?
C0AA C3 1.467(4) . ?
C3 C4 1.378(5) . ?
C3 C7 1.378(5) . ?
C4 H4 0.9300 . ?
C4 C1AA 1.367(4) . ?
C1AA H1AA 0.9300 . ?
C2AA H2AA 0.9300 . ?
C2AA C7 1.367(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.369(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.381(5) . ?
C10 C11 1.375(5) . ?
C10 C13 1.470(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.366(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
Cl1 C1 1.719(4) . ?
Cl2 C1 1.728(5) . ?
Cl3 C1 1.731(5) . ?
C1 H1 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Cu1 O4 167.10(10) . . ?
N2 Cu1 O3 91.46(10) . . ?
N2 Cu1 O4 89.05(10) . . ?
N3 Cu1 O3 90.31(10) . . ?
N3 Cu1 O4 89.98(10) . . ?
N3 Cu1 N2 176.19(11) . . ?
N3AA O3 Cu1 112.9(2) . . ?
N4AA O4 Cu1 103.9(2) . . ?
C0AA N1 N4 111.2(3) . 1_445 ?
C1AA N2 Cu1 119.6(2) . . ?
C1AA N2 C2AA 117.5(3) . . ?
C2AA N2 Cu1 123.0(2) . . ?
C8 N3 Cu1 120.2(2) . . ?
C8 N3 C12 117.1(3) . . ?
C12 N3 Cu1 122.7(2) . . ?
C13 N4 N1 110.9(3) . 1_665 ?
O1 N3AA O3 117.5(3) . . ?
O2 N3AA O1 124.9(3) . . ?
O2 N3AA O3 117.6(3) . . ?
O5 N4AA O4 117.1(3) . . ?
O6 N4AA O4 119.3(3) . . ?
O6 N4AA O5 123.5(3) . . ?
N1 C0AA H0AA 119.9 . . ?
N1 C0AA C3 120.1(3) . . ?
C3 C0AA H0AA 119.9 . . ?
C4 C3 C0AA 120.2(3) . . ?
C4 C3 C7 117.3(3) . . ?
C7 C3 C0AA 122.5(3) . . ?
C3 C4 H4 120.1 . . ?
C1AA C4 C3 119.9(3) . . ?
C1AA C4 H4 120.1 . . ?
N2 C1AA C4 122.8(3) . . ?
N2 C1AA H1AA 118.6 . . ?
C4 C1AA H1AA 118.6 . . ?
N2 C2AA H2AA 118.4 . . ?
N2 C2AA C7 123.2(3) . . ?
C7 C2AA H2AA 118.4 . . ?
C3 C7 H7 120.3 . . ?
C2AA C7 C3 119.4(3) . . ?
C2AA C7 H7 120.3 . . ?
N3 C8 H8 118.4 . . ?
N3 C8 C9 123.3(3) . . ?
C9 C8 H8 118.4 . . ?
C8 C9 H9 120.4 . . ?
C8 C9 C10 119.1(3) . . ?
C10 C9 H9 120.4 . . ?
C9 C10 C13 122.2(3) . . ?
C11 C10 C9 117.7(3) . . ?
C11 C10 C13 120.1(3) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.2(3) . . ?
C12 C11 H11 120.4 . . ?
N3 C12 C11 123.5(3) . . ?
N3 C12 H12 118.2 . . ?
C11 C12 H12 118.2 . . ?
N4 C13 C10 119.9(3) . . ?
N4 C13 H13 120.0 . . ?
C10 C13 H13 120.0 . . ?
Cl1 C1 Cl2 110.7(3) . . ?
Cl1 C1 Cl3 109.9(2) . . ?
Cl1 C1 H1 107.9 . . ?
Cl2 C1 Cl3 112.4(3) . . ?
Cl2 C1 H1 107.9 . . ?
Cl3 C1 H1 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O3 N3AA O1 2.3(3) . . . . ?
Cu1 O3 N3AA O2 -177.1(2) . . . . ?
Cu1 O4 N4AA O5 3.4(3) . . . . ?
Cu1 O4 N4AA O6 -175.0(3) . . . . ?
Cu1 N2 C1AA C4 179.0(3) . . . . ?
Cu1 N2 C2AA C7 -179.4(3) . . . . ?
Cu1 N3 C8 C9 -177.9(3) . . . . ?
Cu1 N3 C12 C11 177.6(3) . . . . ?
N1 N4 C13 C10 178.5(3) 1_665 . . . ?
N1 C0AA C3 C4 175.6(3) . . . . ?
N1 C0AA C3 C7 -3.3(5) . . . . ?
N2 C2AA C7 C3 0.0(5) . . . . ?
N3 C8 C9 C10 -0.2(6) . . . . ?
N4 N1 C0AA C3 -179.8(3) 1_445 . . . ?
C0AA C3 C4 C1AA -178.8(3) . . . . ?
C0AA C3 C7 C2AA 178.3(3) . . . . ?
C3 C4 C1AA N2 0.8(5) . . . . ?
C4 C3 C7 C2AA -0.6(5) . . . . ?
C1AA N2 C2AA C7 1.0(5) . . . . ?
C2AA N2 C1AA C4 -1.4(5) . . . . ?
C7 C3 C4 C1AA 0.2(5) . . . . ?
C8 N3 C12 C11 -2.2(5) . . . . ?
C8 C9 C10 C11 -1.4(5) . . . . ?
C8 C9 C10 C13 -179.7(3) . . . . ?
C9 C10 C11 C12 1.1(5) . . . . ?
C9 C10 C13 N4 1.7(5) . . . . ?
C10 C11 C12 N3 0.7(6) . . . . ?
C11 C10 C13 N4 -176.6(4) . . . . ?
C12 N3 C8 C9 2.0(5) . . . . ?
C13 C10 C11 C12 179.5(3) . . . . ?

_olex2_date_sample_data_collection 2015-10-16
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.058
_oxdiff_exptl_absorpt_empirical_full_min 0.953
_exptl_crystal_preparation       'Magnetic properties,Luminescent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1816300'
_audit_update_record             
;
2018-08-09 deposited with the CCDC.
2018-08-20 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         'C12 H12 Cd N4 O5 S, H2 O'
_chemical_formula_sum            'C12 H14 Cd N4 O6 S'
_chemical_formula_weight         454.73

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 '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                   5.6469(6)
_cell_length_b                   10.3807(8)
_cell_length_c                   30.356(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.598(10)
_cell_angle_gamma                90
_cell_volume                     1773.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    4235
_cell_measurement_theta_min      3.3240
_cell_measurement_theta_max      27.8790

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.383
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.64532
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.1544
_diffrn_reflns_number            11254
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_av_R_equivalents  0.0805
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         3.332
_diffrn_reflns_theta_max         28.288
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.873
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.873
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3851
_reflns_number_gt                3553
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015)'

_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0647P)²+12.7639P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3851
_refine_ls_number_parameters     227
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.1555
_refine_ls_wR_factor_gt          0.1517
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_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
Cd1 Cd 0.92555(6) 0.75748(3) 0.73788(2) 0.01076(15) Uani 1 1 d . . . . .
N1 N 0.4639(8) 0.7903(4) 1.16491(15) 0.0121(9) Uani 1 1 d . . . . .
C2 C 0.2924(11) 0.7548(5) 1.1339(2) 0.0196(12) Uani 1 1 d . . . . .
H2 H 0.1515 0.7165 1.1430 0.023 Uiso 1 1 calc R U . . .
C3 C 0.3146(11) 0.7723(6) 1.0895(2) 0.0213(12) Uani 1 1 d . . . . .
H3 H 0.1890 0.7482 1.0684 0.026 Uiso 1 1 calc R U . . .
C4 C 0.5207(10) 0.8252(5) 1.07571(19) 0.0187(11) Uani 1 1 d . . . . .
C5 C 0.6992(10) 0.8620(5) 1.10762(19) 0.0170(11) Uani 1 1 d . . . . .
H5 H 0.8427 0.8992 1.0993 0.020 Uiso 1 1 calc R U . . .
C6 C 0.6624(10) 0.8430(5) 1.15183(19) 0.0175(11) Uani 1 1 d . . . . .
H6 H 0.7832 0.8686 1.1737 0.021 Uiso 1 1 calc R U . . .
C7 C 0.5509(10) 0.8401(6) 1.0282(2) 0.0228(12) Uani 1 1 d . . . . .
H7 H 0.4177 0.8242 1.0078 0.027 Uiso 1 1 calc R U . . .
N8 N 0.7426(9) 0.8726(5) 1.01326(16) 0.0234(11) Uani 1 1 d . . . . .
N9 N 0.7238(9) 0.8777(6) 0.96713(17) 0.0258(12) Uani 1 1 d . . . . .
C10 C 0.9090(10) 0.8476(6) 0.95008(19) 0.0211(12) Uani 1 1 d . . . . .
H10 H 1.0469 0.8278 0.9689 0.025 Uiso 1 1 calc R U . . .
C11 C 0.9226(10) 0.8416(5) 0.90210(19) 0.0184(11) Uani 1 1 d . . . . .
C12 C 1.1167(11) 0.7879(6) 0.8840(2) 0.0214(12) Uani 1 1 d . . . . .
H12 H 1.2505 0.7605 0.9026 0.026 Uiso 1 1 calc R U . . .
C13 C 1.1150(10) 0.7743(5) 0.83907(19) 0.0159(11) Uani 1 1 d . . . . .
H13 H 1.2493 0.7368 0.8272 0.019 Uiso 1 1 calc R U . . .
N14 N 0.9303(8) 0.8122(4) 0.81102(15) 0.0138(9) Uani 1 1 d . . . . .
C15 C 0.7459(10) 0.8669(5) 0.82865(18) 0.0158(11) Uani 1 1 d . . . . .
H15 H 0.6162 0.8957 0.8093 0.019 Uiso 1 1 calc R U . . .
C16 C 0.7333(10) 0.8840(5) 0.87372(18) 0.0167(11) Uani 1 1 d . . . . .
H16 H 0.5988 0.9237 0.8849 0.020 Uiso 1 1 calc R U . . .
O17 O 0.6052(6) 0.6228(4) 0.73595(13) 0.0163(8) Uani 1 1 d . . . . .
H17A H 0.6724 0.5618 0.7509 0.020 Uiso 1 1 d R U . . .
H17B H 0.4565 0.6141 0.7416 0.020 Uiso 1 1 d R U . . .
O18 O 1.1331(7) 0.5712(3) 0.75979(13) 0.0151(8) Uani 1 1 d . U . . .
O19 O 0.6730(7) 0.9273(3) 0.71929(13) 0.0165(8) Uani 1 1 d . . . . .
S20 S 0.4111(2) 0.94915(11) 0.71688(4) 0.0107(3) Uani 1 1 d . . . . .
O21 O 0.3018(7) 0.8418(3) 0.74046(12) 0.0143(8) Uani 1 1 d . . . . .
O22 O 0.3192(8) 0.9553(4) 0.67087(14) 0.0250(10) Uani 1 1 d . . . . .
O1WA O -0.1182(13) 1.0629(6) 0.6384(3) 0.041(2) Uani 0.763(16) 1 d . . P A 1
H1WA H 0.0206 1.0331 0.6407 0.049 Uiso 0.763(16) 1 d R U P A 1
H1WB H -0.1846 1.0301 0.6600 0.049 Uiso 0.763(16) 1 d R U P A 1
O1WB O -0.007(5) 1.057(2) 0.6001(10) 0.065(12) Uani 0.237(16) 1 d . . P A 2
H1WC H 0.1228 1.0300 0.6121 0.078 Uiso 0.237(16) 1 d R U P A 2
H1WD H -0.1361 1.0771 0.6103 0.078 Uiso 0.237(16) 1 d R U P A 2


_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
Cd1 O17 2.283(4) . ?
Cd1 N14 2.290(5) . ?
Cd1 O21 2.294(4) 1_655 ?
Cd1 N1 2.297(5) 4_675 ?
Cd1 O19 2.309(4) . ?
Cd1 O18 2.330(3) . ?
N1 C6 1.336(8) . ?
N1 C2 1.347(7) . ?
N1 Cd1 2.297(5) 4_576 ?
C2 C3 1.376(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(8) . ?
C4 C7 1.473(8) . ?
C5 C6 1.389(8) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N8 1.253(8) . ?
C7 H7 0.9500 . ?
N8 N9 1.397(7) . ?
N9 C10 1.244(8) . ?
C10 C11 1.466(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(9) . ?
C11 C16 1.390(8) . ?
C12 C13 1.370(8) . ?
C12 H12 0.9500 . ?
C13 N14 1.351(7) . ?
C13 H13 0.9500 . ?
N14 C15 1.336(7) . ?
C15 C16 1.387(8) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
O17 H17A 0.8514 . ?
O17 H17B 0.8745 . ?
O18 S20 1.483(4) 2_646 ?
O19 S20 1.492(4) . ?
S20 O22 1.452(4) . ?
S20 O18 1.483(4) 2_656 ?
S20 O21 1.485(4) . ?
O21 Cd1 2.294(4) 1_455 ?
O1WA H1WA 0.8403 . ?
O1WA H1WB 0.8521 . ?
O1WB H1WC 0.8403 . ?
O1WB H1WD 0.8400 . ?

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
O17 Cd1 N14 97.14(16) . . ?
O17 Cd1 O21 164.70(13) . 1_655 ?
N14 Cd1 O21 86.18(15) . 1_655 ?
O17 Cd1 N1 88.79(15) . 4_675 ?
N14 Cd1 N1 173.67(16) . 4_675 ?
O21 Cd1 N1 87.52(14) 1_655 4_675 ?
O17 Cd1 O19 89.35(13) . . ?
N14 Cd1 O19 90.39(15) . . ?
O21 Cd1 O19 105.61(13) 1_655 . ?
N1 Cd1 O19 91.90(15) 4_675 . ?
O17 Cd1 O18 83.04(14) . . ?
N14 Cd1 O18 87.84(15) . . ?
O21 Cd1 O18 82.16(13) 1_655 . ?
N1 Cd1 O18 90.69(15) 4_675 . ?
O19 Cd1 O18 171.90(14) . . ?
C6 N1 C2 118.5(5) . . ?
C6 N1 Cd1 121.4(3) . 4_576 ?
C2 N1 Cd1 119.8(4) . 4_576 ?
N1 C2 C3 122.1(6) . . ?
N1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C2 C3 C4 119.6(6) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 118.6(6) . . ?
C3 C4 C7 120.3(5) . . ?
C5 C4 C7 121.2(5) . . ?
C6 C5 C4 118.5(5) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
N1 C6 C5 122.7(5) . . ?
N1 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
N8 C7 C4 123.6(5) . . ?
N8 C7 H7 118.2 . . ?
C4 C7 H7 118.2 . . ?
C7 N8 N9 112.0(5) . . ?
C10 N9 N8 114.1(5) . . ?
N9 C10 C11 122.5(5) . . ?
N9 C10 H10 118.8 . . ?
C11 C10 H10 118.8 . . ?
C12 C11 C16 118.5(5) . . ?
C12 C11 C10 121.2(5) . . ?
C16 C11 C10 120.2(5) . . ?
C13 C12 C11 119.6(5) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
N14 C13 C12 122.7(5) . . ?
N14 C13 H13 118.6 . . ?
C12 C13 H13 118.6 . . ?
C15 N14 C13 117.3(5) . . ?
C15 N14 Cd1 123.0(3) . . ?
C13 N14 Cd1 119.2(4) . . ?
N14 C15 C16 123.6(5) . . ?
N14 C15 H15 118.2 . . ?
C16 C15 H15 118.2 . . ?
C15 C16 C11 118.2(5) . . ?
C15 C16 H16 120.9 . . ?
C11 C16 H16 120.9 . . ?
Cd1 O17 H17A 97.1 . . ?
Cd1 O17 H17B 146.0 . . ?
H17A O17 H17B 102.2 . . ?
S20 O18 Cd1 138.2(2) 2_646 . ?
S20 O19 Cd1 135.9(2) . . ?
O22 S20 O18 111.2(2) . 2_656 ?
O22 S20 O21 111.5(2) . . ?
O18 S20 O21 108.6(2) 2_656 . ?
O22 S20 O19 109.3(3) . . ?
O18 S20 O19 108.1(2) 2_656 . ?
O21 S20 O19 108.1(2) . . ?
S20 O21 Cd1 133.6(2) . 1_455 ?
H1WA O1WA H1WB 104.6 . . ?
H1WC O1WB H1WD 132.5 . . ?

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
C6 H6 O17 0.95 2.52 3.446(7) 165.7 4_676
O17 H17A O19 0.85 1.84 2.695(5) 176.8 2_646
O17 H17B O18 0.87 2.00 2.868(6) 171.5 1_455
O1WA H1WA O22 0.84 2.02 2.815(8) 157.5 .
O1WA H1WB O19 0.85 2.29 3.141(9) 173.6 1_455
O1WA H1WA O22 0.84 2.02 2.815(8) 157.5 .

_refine_diff_density_max         1.957
_refine_diff_density_min         -1.762
_refine_diff_density_rms         0.204



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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1816301'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.
2018-08-20 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         'C12 H10 Cu N6 O6, C H2 Cl2'
_chemical_formula_sum            'C13 H12 Cl2 Cu N6 O6'
_chemical_formula_weight         482.73

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           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                   9.4802(3)
_cell_length_b                   11.9554(6)
_cell_length_c                   16.3894(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.085(4)
_cell_angle_gamma                90
_cell_volume                     1856.34(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    3230
_cell_measurement_theta_min      3.6180
_cell_measurement_theta_max      26.3260

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_F_000             972
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    1.510
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.97529
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.2413
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            8016
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.408
_diffrn_reflns_theta_max         26.578
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3592
_reflns_number_gt                2975
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_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)+(0.0541P)²+2.7892P] 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         3592
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1133
_refine_ls_wR_factor_gt          0.1062
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.39671(4) 0.05936(3) 0.41568(2) 0.01786(14) Uani 1 1 d . . . . .
N1 N 0.5361(3) 0.1801(2) 0.40087(16) 0.0182(6) Uani 1 1 d . . . . .
C2 C 0.5518(4) 0.2612(3) 0.4567(2) 0.0239(7) Uani 1 1 d . . . . .
H2 H 0.4930 0.2604 0.5024 0.029 Uiso 1 1 calc R U . . .
C3 C 0.6490(4) 0.3454(3) 0.4510(2) 0.0251(8) Uani 1 1 d . . . . .
H3 H 0.6586 0.4007 0.4925 0.030 Uiso 1 1 calc R U . . .
C4 C 0.7336(4) 0.3487(3) 0.3833(2) 0.0243(8) Uani 1 1 d . . . . .
C5 C 0.7162(4) 0.2655(3) 0.3245(2) 0.0253(8) Uani 1 1 d . . . . .
H5 H 0.7729 0.2651 0.2779 0.030 Uiso 1 1 calc R U . . .
C6 C 0.6162(4) 0.1840(3) 0.3343(2) 0.0243(7) Uani 1 1 d . . . . .
H6 H 0.6028 0.1287 0.2931 0.029 Uiso 1 1 calc R U . . .
C7 C 0.8384(4) 0.4380(3) 0.3720(2) 0.0267(8) Uani 1 1 d . . . . .
H7 H 0.9101 0.4295 0.3334 0.032 Uiso 1 1 calc R U . . .
N8 N 0.8315(3) 0.5266(3) 0.4147(2) 0.0313(7) Uani 1 1 d . . . . .
N9 N 0.9366(3) 0.6043(3) 0.39365(19) 0.0292(7) Uani 1 1 d . . . . .
C10 C 0.9499(4) 0.6808(3) 0.4477(2) 0.0266(8) Uani 1 1 d . . . . .
H10 H 0.8927 0.6804 0.4941 0.032 Uiso 1 1 calc R U . . .
C11 C 1.0548(3) 0.7695(3) 0.4372(2) 0.0205(7) Uani 1 1 d . . . . .
C12 C 1.1387(3) 0.7757(3) 0.3685(2) 0.0233(7) Uani 1 1 d . . . . .
H12 H 1.1292 0.7214 0.3264 0.028 Uiso 1 1 calc R U . . .
C13 C 1.2343(3) 0.8607(3) 0.3629(2) 0.0224(7) Uani 1 1 d . . . . .
H13 H 1.2895 0.8648 0.3158 0.027 Uiso 1 1 calc R U . . .
N14 N 1.2535(3) 0.9389(2) 0.42145(16) 0.0180(6) Uani 1 1 d . . . . .
C15 C 1.1720(3) 0.9338(3) 0.4871(2) 0.0213(7) Uani 1 1 d . . . . .
H15 H 1.1829 0.9895 0.5282 0.026 Uiso 1 1 calc R U . . .
C16 C 1.0737(3) 0.8507(3) 0.4966(2) 0.0233(7) Uani 1 1 d . . . . .
H16 H 1.0188 0.8491 0.5439 0.028 Uiso 1 1 calc R U . . .
O21 O 0.1152(3) 0.2642(2) 0.33151(19) 0.0435(7) Uani 1 1 d . . . . .
N21 N 0.2080(3) 0.1955(3) 0.34683(19) 0.0277(7) Uani 1 1 d . . . . .
O22 O 0.2708(3) 0.1420(2) 0.29375(15) 0.0336(6) Uani 1 1 d . . . . .
O23 O 0.2439(2) 0.17476(19) 0.42206(14) 0.0226(5) Uani 1 1 d . . . . .
N31 N 0.5942(3) -0.1041(3) 0.37323(17) 0.0235(6) Uani 1 1 d . . . . .
O31 O 0.6840(3) -0.1768(3) 0.38276(17) 0.0458(8) Uani 1 1 d . . . . .
O32 O 0.5396(3) -0.0774(2) 0.30731(14) 0.0305(6) Uani 1 1 d . . . . .
O33 O 0.5532(2) -0.05191(18) 0.43811(13) 0.0196(5) Uani 1 1 d . . . . .
C1S C 0.0041(5) 0.0691(4) 0.1876(3) 0.0522(12) Uani 1 1 d . . . . .
H1S1 H -0.0716 0.0766 0.1447 0.063 Uiso 1 1 calc R U . . .
H1S2 H 0.0438 0.1443 0.1988 0.063 Uiso 1 1 calc R U . . .
Cl1S Cl 0.13883(13) -0.02000(12) 0.15201(7) 0.0559(3) Uani 1 1 d . . . . .
Cl2S Cl -0.06883(12) 0.01390(10) 0.27896(7) 0.0464(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
Cu1 N1 1.979(3) . ?
Cu1 N14 1.984(3) 1_445 ?
Cu1 O23 2.006(2) . ?
Cu1 O33 2.016(2) . ?
Cu1 O33 2.427(2) 3_656 ?
N1 C2 1.338(4) . ?
N1 C6 1.352(4) . ?
C2 C3 1.370(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(5) . ?
C4 C7 1.475(5) . ?
C5 C6 1.373(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N8 1.273(5) . ?
C7 H7 0.9500 . ?
N8 N9 1.413(4) . ?
N9 C10 1.276(5) . ?
C10 C11 1.468(5) . ?
C10 H10 0.9500 . ?
C11 C16 1.381(5) . ?
C11 C12 1.404(5) . ?
C12 C13 1.366(5) . ?
C12 H12 0.9500 . ?
C13 N14 1.347(4) . ?
C13 H13 0.9500 . ?
N14 C15 1.348(4) . ?
N14 Cu1 1.984(3) 1_665 ?
C15 C16 1.375(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
O21 N21 1.224(4) . ?
N21 O22 1.248(4) . ?
N21 O23 1.291(4) . ?
N31 O31 1.222(4) . ?
N31 O32 1.223(4) . ?
N31 O33 1.304(3) . ?
O33 Cu1 2.428(2) 3_656 ?
C1S Cl1S 1.777(5) . ?
C1S Cl2S 1.798(5) . ?
C1S H1S1 0.9900 . ?
C1S H1S2 0.9900 . ?

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 N14 175.63(11) . 1_445 ?
N1 Cu1 O23 89.50(10) . . ?
N14 Cu1 O23 90.01(10) 1_445 . ?
N1 Cu1 O33 90.77(10) . . ?
N14 Cu1 O33 90.72(10) 1_445 . ?
O23 Cu1 O33 166.45(9) . . ?
N1 Cu1 O33 92.31(9) . 3_656 ?
N14 Cu1 O33 92.06(9) 1_445 3_656 ?
O23 Cu1 O33 95.13(9) . 3_656 ?
O33 Cu1 O33 71.32(9) . 3_656 ?
C2 N1 C6 118.4(3) . . ?
C2 N1 Cu1 120.2(2) . . ?
C6 N1 Cu1 121.4(2) . . ?
N1 C2 C3 123.0(3) . . ?
N1 C2 H2 118.5 . . ?
C3 C2 H2 118.5 . . ?
C2 C3 C4 118.9(3) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 118.3(3) . . ?
C5 C4 C7 119.7(3) . . ?
C3 C4 C7 122.0(3) . . ?
C6 C5 C4 119.5(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
N1 C6 C5 121.9(3) . . ?
N1 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
N8 C7 C4 119.0(3) . . ?
N8 C7 H7 120.5 . . ?
C4 C7 H7 120.5 . . ?
C7 N8 N9 111.2(3) . . ?
C10 N9 N8 110.8(3) . . ?
N9 C10 C11 119.2(3) . . ?
N9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C16 C11 C12 117.7(3) . . ?
C16 C11 C10 119.7(3) . . ?
C12 C11 C10 122.5(3) . . ?
C13 C12 C11 119.3(3) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
N14 C13 C12 122.7(3) . . ?
N14 C13 H13 118.6 . . ?
C12 C13 H13 118.6 . . ?
C13 N14 C15 118.0(3) . . ?
C13 N14 Cu1 123.0(2) . 1_665 ?
C15 N14 Cu1 118.9(2) . 1_665 ?
N14 C15 C16 122.3(3) . . ?
N14 C15 H15 118.9 . . ?
C16 C15 H15 118.9 . . ?
C15 C16 C11 119.9(3) . . ?
C15 C16 H16 120.1 . . ?
C11 C16 H16 120.1 . . ?
O21 N21 O22 124.0(3) . . ?
O21 N21 O23 119.2(3) . . ?
O22 N21 O23 116.8(3) . . ?
N21 O23 Cu1 104.35(19) . . ?
O31 N31 O32 124.6(3) . . ?
O31 N31 O33 117.6(3) . . ?
O32 N31 O33 117.8(3) . . ?
N31 O33 Cu1 114.0(2) . . ?
N31 O33 Cu1 137.2(2) . 3_656 ?
Cu1 O33 Cu1 108.68(9) . 3_656 ?
Cl1S C1S Cl2S 110.9(3) . . ?
Cl1S C1S H1S1 109.5 . . ?
Cl2S C1S H1S1 109.5 . . ?
Cl1S C1S H1S2 109.5 . . ?
Cl2S C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C3 -2.6(5) . . . . ?
Cu1 N1 C2 C3 178.3(3) . . . . ?
N1 C2 C3 C4 1.4(6) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C2 C3 C4 C7 178.7(3) . . . . ?
C3 C4 C5 C6 0.6(5) . . . . ?
C7 C4 C5 C6 -178.5(3) . . . . ?
C2 N1 C6 C5 2.8(5) . . . . ?
Cu1 N1 C6 C5 -178.1(3) . . . . ?
C4 C5 C6 N1 -1.8(5) . . . . ?
C5 C4 C7 N8 163.6(4) . . . . ?
C3 C4 C7 N8 -15.5(6) . . . . ?
C4 C7 N8 N9 -177.8(3) . . . . ?
C7 N8 N9 C10 -165.5(3) . . . . ?
N8 N9 C10 C11 179.7(3) . . . . ?
N9 C10 C11 C16 -177.8(3) . . . . ?
N9 C10 C11 C12 2.0(5) . . . . ?
C16 C11 C12 C13 -0.2(5) . . . . ?
C10 C11 C12 C13 -179.9(3) . . . . ?
C11 C12 C13 N14 1.0(5) . . . . ?
C12 C13 N14 C15 -1.6(5) . . . . ?
C12 C13 N14 Cu1 177.8(3) . . . 1_665 ?
C13 N14 C15 C16 1.5(5) . . . . ?
Cu1 N14 C15 C16 -177.9(3) 1_665 . . . ?
N14 C15 C16 C11 -0.7(5) . . . . ?
C12 C11 C16 C15 0.1(5) . . . . ?
C10 C11 C16 C15 179.8(3) . . . . ?
O21 N21 O23 Cu1 -179.9(3) . . . . ?
O22 N21 O23 Cu1 0.8(3) . . . . ?
O31 N31 O33 Cu1 -176.5(2) . . . . ?
O32 N31 O33 Cu1 3.1(3) . . . . ?
O31 N31 O33 Cu1 -1.6(5) . . . 3_656 ?
O32 N31 O33 Cu1 178.0(2) . . . 3_656 ?

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
C6 H6 O32 0.95 2.55 3.235(4) 129.3 .
C7 H7 O32 0.95 2.37 3.202(4) 145.5 2_655
C12 H12 O22 0.95 2.41 3.245(4) 146.4 2_655
C13 H13 O32 0.95 2.48 3.153(4) 128.1 1_665

_refine_diff_density_max         0.966
_refine_diff_density_min         -1.031
_refine_diff_density_rms         0.088

