# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_YP61
_database_code_depnum_ccdc_archive 'CCDC 1514999'
_audit_update_record             
;
2016-11-03 deposited with the CCDC.
2017-01-25 downloaded from the CCDC.
;
_audit_creation_date             2016-07-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 Cl Cu N3 O2, H2 O, N O3'
_chemical_formula_sum            'C12 H13 Cl Cu N4 O6'
_chemical_formula_weight         408.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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        P2(1)/c
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.7998(14)
_cell_length_b                   8.7712(16)
_cell_length_c                   22.671(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.976(8)
_cell_angle_gamma                90
_cell_volume                     1532.0(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4660
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      27.585
_cell_measurement_theta_min      2.494
_shelx_estimated_absorpt_T_max   0.853
_shelx_estimated_absorpt_T_min   0.828
_exptl_absorpt_coefficient_mu    1.639
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1612 before and 0.0560 after correction.
The Ratio of minimum to maximum transmission is 0.6212.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.770
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             828
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0818
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            19721
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.171
_diffrn_reflns_theta_min         2.494
_diffrn_ambient_temperature      301.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'high brilliance microfocus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2693
_reflns_number_total             3763
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker Apex3, 2016'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3763
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0404P)²+0.6041P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0925
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O3(H3A,H3B)
2.b Rotating group:
 O2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2C), C3(H3), C5(H5), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.31803(4) 0.34574(3) 0.43043(2) 0.02647(11) Uani 1 1 d . . . . .
Cl1 Cl 0.30415(11) 0.55390(9) 0.73869(4) 0.0456(2) Uani 1 1 d . . . . .
O1 O 0.3927(3) 0.2822(2) 0.50916(9) 0.0325(5) Uani 1 1 d . . . . .
N1 N 0.2116(3) 0.5302(2) 0.45581(10) 0.0264(5) Uani 1 1 d . . . . .
C1 C 0.3711(3) 0.3518(3) 0.55892(12) 0.0263(6) Uani 1 1 d . . . . .
O2 O 0.4413(3) 0.1756(2) 0.39934(9) 0.0340(5) Uani 1 1 d . . . . .
H2A H 0.5129 0.1367 0.4280 0.051 Uiso 1 1 d GR . . . .
H2B H 0.3744 0.0974 0.3934 0.051 Uiso 1 1 d GR . . . .
N2 N 0.1391(3) 0.6176(2) 0.40865(11) 0.0322(6) Uani 1 1 d . . . . .
H2 H 0.0848 0.7008 0.4137 0.039 Uiso 1 1 calc R . . . .
C2 C 0.4421(4) 0.2830(3) 0.61351(13) 0.0321(7) Uani 1 1 d . . . . .
H2C H 0.5041 0.1927 0.6128 0.038 Uiso 1 1 calc R . . . .
O3 O 0.6873(3) 0.0323(2) 0.47351(11) 0.0434(5) Uani 1 1 d . . . . .
H3A H 0.6463 -0.0535 0.4818 0.065 Uiso 1 1 d G . . . .
H3B H 0.7805 0.0185 0.4591 0.065 Uiso 1 1 d G . . . .
N3 N 0.2365(3) 0.4321(2) 0.35121(11) 0.0283(5) Uani 1 1 d . . . . .
C3 C 0.4226(4) 0.3450(3) 0.66734(13) 0.0323(6) Uani 1 1 d . . . . .
H3 H 0.4707 0.2970 0.7026 0.039 Uiso 1 1 calc R . . . .
O4 O 0.0485(3) 0.1488(2) 0.41625(11) 0.0495(6) Uani 1 1 d . . . . .
N4 N 0.0656(3) 0.0128(3) 0.40384(11) 0.0346(6) Uani 1 1 d . . . . .
C4 C 0.3303(4) 0.4804(3) 0.66908(13) 0.0297(6) Uani 1 1 d . . . . .
O5 O -0.0352(3) -0.0856(3) 0.41786(12) 0.0550(7) Uani 1 1 d . . . . .
C5 C 0.2627(4) 0.5528(3) 0.61787(13) 0.0304(6) Uani 1 1 d . . . . .
H5 H 0.2029 0.6440 0.6198 0.036 Uiso 1 1 calc R . . . .
O6 O 0.1846(3) -0.0291(2) 0.37652(11) 0.0462(6) Uani 1 1 d . . . . .
C6 C 0.2818(3) 0.4919(3) 0.56178(13) 0.0258(6) Uani 1 1 d . . . . .
C7 C 0.2071(4) 0.5760(3) 0.50961(13) 0.0288(6) Uani 1 1 d . . . . .
H7 H 0.1527 0.6682 0.5149 0.035 Uiso 1 1 calc R . . . .
C8 C 0.1568(3) 0.5667(3) 0.35331(13) 0.0276(6) Uani 1 1 d . . . . .
C9 C 0.0958(4) 0.6497(3) 0.30228(14) 0.0372(7) Uani 1 1 d . . . . .
H9 H 0.0402 0.7427 0.3049 0.045 Uiso 1 1 calc R . . . .
C10 C 0.1190(4) 0.5920(4) 0.24811(15) 0.0413(8) Uani 1 1 d . . . . .
H10 H 0.0785 0.6453 0.2133 0.050 Uiso 1 1 calc R . . . .
C11 C 0.2033(4) 0.4532(3) 0.24531(14) 0.0387(7) Uani 1 1 d . . . . .
H11 H 0.2211 0.4131 0.2088 0.046 Uiso 1 1 calc R . . . .
C12 C 0.2594(4) 0.3772(3) 0.29706(14) 0.0347(7) Uani 1 1 d . . . . .
H12 H 0.3155 0.2842 0.2952 0.042 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 O1 1.874(2) . ?
Cu1 N1 1.946(2) . ?
Cu1 O2 1.9645(18) . ?
Cu1 N3 1.961(2) . ?
Cl1 C4 1.746(3) . ?
O1 C1 1.317(3) . ?
N1 N2 1.365(3) . ?
N1 C7 1.290(3) . ?
C1 C2 1.410(4) . ?
C1 C6 1.419(3) . ?
O2 H2A 0.8590 . ?
O2 H2B 0.8596 . ?
N2 H2 0.8600 . ?
N2 C8 1.359(4) . ?
C2 H2C 0.9300 . ?
C2 C3 1.366(4) . ?
O3 H3A 0.8499 . ?
O3 H3B 0.8503 . ?
N3 C8 1.339(3) . ?
N3 C12 1.356(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(4) . ?
O4 N4 1.238(3) . ?
N4 O5 1.242(3) . ?
N4 O6 1.249(3) . ?
C4 C5 1.356(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.409(4) . ?
C6 C7 1.438(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.387(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.366(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.390(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.361(4) . ?
C12 H12 0.9300 . ?

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 92.83(9) . . ?
O1 Cu1 O2 91.08(8) . . ?
O1 Cu1 N3 174.41(8) . . ?
N1 Cu1 O2 173.13(9) . . ?
N1 Cu1 N3 81.80(9) . . ?
N3 Cu1 O2 94.11(9) . . ?
C1 O1 Cu1 128.01(17) . . ?
N2 N1 Cu1 112.29(17) . . ?
C7 N1 Cu1 127.88(19) . . ?
C7 N1 N2 119.8(2) . . ?
O1 C1 C2 117.9(2) . . ?
O1 C1 C6 124.8(3) . . ?
C2 C1 C6 117.3(2) . . ?
Cu1 O2 H2A 109.1 . . ?
Cu1 O2 H2B 110.1 . . ?
H2A O2 H2B 96.1 . . ?
N1 N2 H2 121.7 . . ?
C8 N2 N1 116.7(2) . . ?
C8 N2 H2 121.7 . . ?
C1 C2 H2C 119.0 . . ?
C3 C2 C1 122.1(3) . . ?
C3 C2 H2C 119.0 . . ?
H3A O3 H3B 109.5 . . ?
C8 N3 Cu1 113.20(19) . . ?
C8 N3 C12 118.2(2) . . ?
C12 N3 Cu1 128.48(19) . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.6(3) . . ?
C4 C3 H3 120.2 . . ?
O4 N4 O5 121.1(3) . . ?
O4 N4 O6 120.8(3) . . ?
O5 N4 O6 118.1(2) . . ?
C3 C4 Cl1 118.3(2) . . ?
C5 C4 Cl1 121.1(2) . . ?
C5 C4 C3 120.6(3) . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.9(2) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C7 123.1(2) . . ?
C5 C6 C1 119.4(3) . . ?
C5 C6 C7 117.5(2) . . ?
N1 C7 C6 123.4(2) . . ?
N1 C7 H7 118.3 . . ?
C6 C7 H7 118.3 . . ?
N2 C8 C9 121.8(2) . . ?
N3 C8 N2 115.9(2) . . ?
N3 C8 C9 122.3(3) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 C8 118.6(3) . . ?
C10 C9 H9 120.7 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.7(3) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 120.6 . . ?
C12 C11 C10 118.7(3) . . ?
C12 C11 H11 120.6 . . ?
N3 C12 C11 122.4(3) . . ?
N3 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?

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
O2 H2A O3 0.86 1.82 2.662(3) 165.7 .
O2 H2B O6 0.86 1.84 2.679(3) 164.1 .
N2 H2 O5 0.86 2.10 2.959(3) 173.4 1_565
O3 H3A O1 0.85 2.04 2.868(3) 163.3 3_656
O3 H3B O5 0.85 2.05 2.863(3) 160.3 1_655

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_YP72
_database_code_depnum_ccdc_archive 'CCDC 1515000'
_audit_update_record             
;
2016-11-03 deposited with the CCDC.
2017-01-25 downloaded from the CCDC.
;
_audit_creation_date             2016-07-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H13 Cl Cu N3 O3, N O3'
_chemical_formula_sum            'C12 H13 Cl Cu N4 O6'
_chemical_formula_weight         408.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0921(7)
_cell_length_b                   8.6878(7)
_cell_length_c                   11.3269(9)
_cell_angle_alpha                91.319(3)
_cell_angle_beta                 103.562(3)
_cell_angle_gamma                100.716(3)
_cell_volume                     758.75(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7712
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.540
_cell_measurement_theta_min      2.392
_shelx_estimated_absorpt_T_max   0.852
_shelx_estimated_absorpt_T_min   0.801
_exptl_absorpt_coefficient_mu    1.655
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1514 before and 0.0768 after correction.
The Ratio of minimum to maximum transmission is 0.6495.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             414
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15328
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.559
_diffrn_reflns_theta_min         2.392
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'high brilliance microfocus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3779
_reflns_number_total             4634
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker Apex3, 2016'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.827
_refine_diff_density_min         -1.115
_refine_diff_density_rms         0.135
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4634
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0507
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0690P)²+1.2933P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1362
_refine_ls_wR_factor_ref         0.1449
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Rotating group:
 O2(H2B,H2C), O3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), N2(H2A), C3(H3), C4(H4), C6(H6), C8(H8), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3263(4) 0.8739(4) 0.8531(3) 0.0208(6) Uani 1 1 d . . . . .
H1 H 0.3899 0.9753 0.8459 0.025 Uiso 1 1 calc R . . . .
Cl1 Cl 0.27626(11) 0.26018(9) 0.07038(7) 0.02585(18) Uani 1 1 d . . . . .
Cu1 Cu 0.37364(5) 0.77829(4) 0.60669(3) 0.01516(12) Uani 1 1 d . . . . .
N1 N 0.2973(3) 0.7605(3) 0.7610(2) 0.0163(5) Uani 1 1 d . . . . .
O1 O 0.4456(3) 0.7670(2) 0.45804(18) 0.0174(4) Uani 1 1 d . . . . .
C2 C 0.2661(4) 0.8455(4) 0.9556(3) 0.0232(6) Uani 1 1 d . . . . .
H2 H 0.2861 0.9263 1.0181 0.028 Uiso 1 1 calc R . . . .
N2 N 0.1682(3) 0.5131(3) 0.6721(2) 0.0165(5) Uani 1 1 d . . . . .
H2A H 0.1008 0.4203 0.6689 0.020 Uiso 1 1 calc R . . . .
O2 O 0.5482(3) 0.9742(2) 0.6668(2) 0.0190(4) Uani 1 1 d . . . . .
H2B H 0.6531 0.9570 0.6706 0.028 Uiso 1 1 d GR . . . .
H2C H 0.5397 1.0436 0.6114 0.028 Uiso 1 1 d GR . . . .
C3 C 0.1750(4) 0.6956(4) 0.9662(3) 0.0227(6) Uani 1 1 d . . . . .
H3 H 0.1349 0.6731 1.0376 0.027 Uiso 1 1 calc R . . . .
N3 N 0.2439(3) 0.5607(3) 0.5787(2) 0.0130(4) Uani 1 1 d . . . . .
O3 O 0.1751(4) 0.9303(3) 0.5482(2) 0.0349(6) Uani 1 1 d . . . . .
H3A H 0.1729 0.9906 0.6105 0.052 Uiso 1 1 d GR . . . .
H3B H 0.1537 0.9357 0.4693 0.052 Uiso 1 1 d GR . . . .
C4 C 0.1427(4) 0.5803(4) 0.8741(3) 0.0204(6) Uani 1 1 d . . . . .
H4 H 0.0809 0.4778 0.8802 0.025 Uiso 1 1 calc R . . . .
N4 N 0.9793(3) 1.1254(3) 0.7331(3) 0.0210(5) Uani 1 1 d . . . . .
O4 O 0.8999(3) 0.9880(3) 0.6954(2) 0.0251(5) Uani 1 1 d . . . . .
C5 C 0.2046(4) 0.6196(3) 0.7705(3) 0.0153(5) Uani 1 1 d . . . . .
O5 O 1.1236(3) 1.1760(3) 0.7078(3) 0.0312(6) Uani 1 1 d . . . . .
C6 C 0.2246(4) 0.4620(3) 0.4868(3) 0.0150(5) Uani 1 1 d . . . . .
H6 H 0.1577 0.3597 0.4864 0.018 Uiso 1 1 calc R . . . .
O6 O 0.9121(4) 1.2164(4) 0.7817(3) 0.0509(9) Uani 1 1 d . . . . .
C7 C 0.2998(4) 0.4997(3) 0.3849(3) 0.0142(5) Uani 1 1 d . . . . .
C8 C 0.2627(4) 0.3805(3) 0.2894(3) 0.0174(5) Uani 1 1 d . . . . .
H8 H 0.1899 0.2828 0.2943 0.021 Uiso 1 1 calc R . . . .
C9 C 0.3312(4) 0.4053(4) 0.1900(3) 0.0178(5) Uani 1 1 d . . . . .
C10 C 0.4413(4) 0.5453(4) 0.1817(3) 0.0189(6) Uani 1 1 d . . . . .
H10 H 0.4906 0.5601 0.1135 0.023 Uiso 1 1 calc R . . . .
C11 C 0.4787(4) 0.6635(3) 0.2739(3) 0.0169(5) Uani 1 1 d . . . . .
H11 H 0.5544 0.7591 0.2679 0.020 Uiso 1 1 calc R . . . .
C12 C 0.4076(4) 0.6458(3) 0.3762(3) 0.0143(5) 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
C1 H1 0.9500 . ?
C1 N1 1.365(4) . ?
C1 C2 1.371(4) . ?
Cl1 C9 1.748(3) . ?
Cu1 N1 1.986(2) . ?
Cu1 O1 1.912(2) . ?
Cu1 O2 1.989(2) . ?
Cu1 N3 1.963(2) . ?
Cu1 O3 2.257(2) . ?
N1 C5 1.332(4) . ?
O1 C12 1.328(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.395(5) . ?
N2 H2A 0.8800 . ?
N2 N3 1.377(3) . ?
N2 C5 1.372(4) . ?
O2 H2B 0.8800 . ?
O2 H2C 0.8799 . ?
C3 H3 0.9500 . ?
C3 C4 1.374(5) . ?
N3 C6 1.294(4) . ?
O3 H3A 0.8740 . ?
O3 H3B 0.8736 . ?
C4 H4 0.9500 . ?
C4 C5 1.406(4) . ?
N4 O4 1.258(3) . ?
N4 O5 1.268(3) . ?
N4 O6 1.226(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.442(4) . ?
C7 C8 1.419(4) . ?
C7 C12 1.420(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.371(4) . ?
C9 C10 1.388(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.409(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 H1 119.1 . . ?
N1 C1 C2 121.9(3) . . ?
C2 C1 H1 119.1 . . ?
N1 Cu1 O2 93.72(9) . . ?
N1 Cu1 O3 86.90(10) . . ?
O1 Cu1 N1 172.65(9) . . ?
O1 Cu1 O2 91.76(9) . . ?
O1 Cu1 N3 92.30(9) . . ?
O1 Cu1 O3 98.20(9) . . ?
O2 Cu1 O3 87.84(10) . . ?
N3 Cu1 N1 81.18(10) . . ?
N3 Cu1 O2 165.01(10) . . ?
N3 Cu1 O3 105.83(11) . . ?
C1 N1 Cu1 127.9(2) . . ?
C5 N1 C1 118.7(2) . . ?
C5 N1 Cu1 113.4(2) . . ?
C12 O1 Cu1 127.80(18) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.7(3) . . ?
C3 C2 H2 120.7 . . ?
N3 N2 H2A 122.1 . . ?
C5 N2 H2A 122.1 . . ?
C5 N2 N3 115.7(2) . . ?
Cu1 O2 H2B 109.9 . . ?
Cu1 O2 H2C 110.0 . . ?
H2B O2 H2C 101.1 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
N2 N3 Cu1 112.86(18) . . ?
C6 N3 Cu1 128.27(19) . . ?
C6 N3 N2 118.9(2) . . ?
Cu1 O3 H3A 109.6 . . ?
Cu1 O3 H3B 109.3 . . ?
H3A O3 H3B 136.1 . . ?
C3 C4 H4 121.2 . . ?
C3 C4 C5 117.6(3) . . ?
C5 C4 H4 121.2 . . ?
O4 N4 O5 118.9(3) . . ?
O6 N4 O4 121.4(3) . . ?
O6 N4 O5 119.2(3) . . ?
N1 C5 N2 116.7(2) . . ?
N1 C5 C4 122.7(3) . . ?
N2 C5 C4 120.7(3) . . ?
N3 C6 H6 118.4 . . ?
N3 C6 C7 123.2(3) . . ?
C7 C6 H6 118.4 . . ?
C8 C7 C6 116.6(2) . . ?
C8 C7 C12 119.3(3) . . ?
C12 C7 C6 124.1(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 Cl1 119.7(2) . . ?
C8 C9 C10 121.1(3) . . ?
C10 C9 Cl1 119.2(2) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.3(3) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.1 . . ?
C10 C11 C12 121.9(3) . . ?
C12 C11 H11 119.1 . . ?
O1 C12 C7 124.2(3) . . ?
O1 C12 C11 117.8(2) . . ?
C11 C12 C7 117.9(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O5 0.88 2.21 2.933(4) 139.1 1_445
O2 H2B O4 0.88 1.92 2.767(3) 162.0 .
O2 H2C O1 0.88 1.84 2.682(3) 160.6 2_676
O3 H3A O4 0.87 2.61 3.180(4) 124.2 1_455
O3 H3A O5 0.87 2.08 2.917(4) 159.4 1_455
O3 H3B N4 0.87 2.30 3.128(4) 159.2 2_676
O3 H3B O4 0.87 1.97 2.820(3) 162.9 2_676

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1515001'
_audit_update_record             
;
2016-11-03 deposited with the CCDC.
2017-01-25 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         'C28 H22 Cl2 Cu2 N8 O2, 2(Cl O4), 4(H2 O)'
_chemical_formula_sum            'C28 H30 Cl4 Cu2 N8 O14'
_chemical_formula_weight         971.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9846(4)
_cell_length_b                   11.4155(5)
_cell_length_c                   12.6028(8)
_cell_angle_alpha                107.849(5)
_cell_angle_beta                 97.174(5)
_cell_angle_gamma                94.306(4)
_cell_volume                     942.14(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2846
_cell_measurement_theta_min      3.7271
_cell_measurement_theta_max      71.0439

_exptl_crystal_description       
;
prism
;
_exptl_crystal_colour            
;
blue-green
;
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    4.678
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.63342
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0309
_diffrn_reflns_number            6047
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.098
_diffrn_reflns_theta_max         71.183
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.956
_reflns_number_total             3546
_reflns_number_gt                3021
_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, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'Shelxt (Shedlrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXT (Sheldrick, 2008)'
_computing_publication_material  'SHELXT (Sheldrick, 2008)'
_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)+(0.1311P)²+0.2165P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3546
_refine_ls_number_parameters     282
_refine_ls_number_restraints     68
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.1836
_refine_ls_wR_factor_gt          0.1710
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.064
_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 0.05374(6) 0.22564(4) 0.87838(4) 0.04410(16) Uani 1 1 d . . . . .
Cl1 Cl 0.54376(13) 0.83492(8) 1.20301(8) 0.0598(2) Uani 1 1 d . . . . .
O1 O 0.1772(4) 0.3205(2) 1.0235(2) 0.0507(6) Uani 1 1 d . . . . .
N1 N -0.0686(4) 0.1386(3) 0.7202(2) 0.0467(6) Uani 1 1 d . . . . .
N2 N 0.0816(4) 0.3643(2) 0.8212(2) 0.0421(6) Uani 1 1 d . . . . .
C6 C 0.1607(5) 0.4768(3) 0.8755(3) 0.0447(7) Uani 1 1 d . . . . .
H3 H 0.1610 0.5346 0.8371 0.054 Uiso 1 1 calc R U . . .
N4 N 0.0164(4) 0.0868(2) 0.9439(2) 0.0463(6) Uani 1 1 d . . . . .
C1 C -0.1443(5) 0.0184(3) 0.6699(3) 0.0548(8) Uani 1 1 d . . . . .
H1 H -0.1341 -0.0362 0.7114 0.066 Uiso 1 1 calc R U . . .
C2 C -0.2350(6) -0.0252(4) 0.5606(4) 0.0642(10) Uani 1 1 d . . . . .
H2 H -0.2854 -0.1082 0.5282 0.077 Uiso 1 1 calc R U . . .
C3 C -0.2507(6) 0.0554(4) 0.4993(3) 0.0682(11) Uani 1 1 d . . . . .
H3A H -0.3150 0.0272 0.4253 0.082 Uiso 1 1 calc R U . . .
C4 C -0.1727(6) 0.1772(4) 0.5461(3) 0.0635(10) Uani 1 1 d . . . . .
H4 H -0.1817 0.2320 0.5047 0.076 Uiso 1 1 calc R U . . .
C5 C -0.0789(5) 0.2163(3) 0.6582(3) 0.0474(7) Uani 1 1 d . . . . .
N3 N 0.0055(4) 0.3344(3) 0.7097(2) 0.0513(7) Uani 1 1 d . . . . .
H6 H 0.0108 0.3877 0.6742 0.062 Uiso 1 1 calc R U . . .
C7 C 0.2476(4) 0.5166(3) 0.9918(3) 0.0424(6) Uani 1 1 d . . . . .
C8 C 0.3344(5) 0.6390(3) 1.0388(3) 0.0455(7) Uani 1 1 d . . . . .
H8 H 0.3310 0.6915 0.9950 0.055 Uiso 1 1 calc R U . . .
C9 C 0.4248(5) 0.6829(3) 1.1490(3) 0.0491(8) Uani 1 1 d . . . . .
C10 C 0.4301(5) 0.6062(3) 1.2161(3) 0.0515(8) Uani 1 1 d . . . . .
H10 H 0.4914 0.6365 1.2907 0.062 Uiso 1 1 calc R U . . .
C11 C 0.3454(5) 0.4865(3) 1.1723(3) 0.0527(8) Uani 1 1 d . . . . .
H11 H 0.3491 0.4362 1.2181 0.063 Uiso 1 1 calc R U . . .
C12 C 0.2520(5) 0.4366(3) 1.0590(3) 0.0436(7) Uani 1 1 d . . . . .
C13 C 0.1696(5) 0.0651(3) 1.0066(3) 0.0524(8) Uani 1 1 d . . . . .
H13 H 0.2901 0.1095 1.0133 0.063 Uiso 1 1 calc R U . . .
C14 C -0.1536(5) 0.0214(3) 0.9382(3) 0.0502(8) Uani 1 1 d . . . . .
H14 H -0.2639 0.0347 0.8958 0.060 Uiso 1 1 calc R U . . .
Cl2 Cl 0.3313(4) 0.8052(2) 0.76685(19) 0.0670(5) Uani 0.714(4) 1 d D U P A 1
O11 O 0.2958(13) 0.6749(6) 0.7233(8) 0.152(3) Uani 0.714(4) 1 d D U P A 1
O12 O 0.1788(11) 0.8688(8) 0.7412(6) 0.148(3) Uani 0.714(4) 1 d D U P A 1
O13 O 0.4897(11) 0.8432(7) 0.7229(6) 0.150(3) Uani 0.714(4) 1 d D U P A 1
O14 O 0.3867(11) 0.8437(8) 0.8860(5) 0.124(2) Uani 0.714(4) 1 d D U P A 1
Cl2A Cl 0.2836(10) 0.7901(5) 0.7648(5) 0.0670(5) Uani 0.286(4) 1 d D . P A 2
O11A O 0.316(3) 0.7043(13) 0.6627(13) 0.152(3) Uani 0.286(4) 1 d D . P A 2
O12A O 0.0904(17) 0.7658(17) 0.7775(14) 0.148(3) Uani 0.286(4) 1 d D . P A 2
O13A O 0.309(3) 0.9087(12) 0.7535(16) 0.150(3) Uani 0.286(4) 1 d D . P A 2
O14A O 0.409(2) 0.7833(18) 0.8549(12) 0.124(2) Uani 0.286(4) 1 d D . P A 2
O1W O -0.0643(9) 0.5234(5) 0.6043(4) 0.1247(16) Uani 1 1 d D U . . .
H1W1 H 0.026(5) 0.485(5) 0.576(5) 0.187 Uiso 1 1 d D U . . .
H1W2 H -0.155(5) 0.467(4) 0.590(7) 0.187 Uiso 1 1 d D U . . .
O2W O 0.5942(18) 0.6105(15) 0.5402(12) 0.321(6) Uani 1 1 d D U . . .
H2W1 H 0.691(7) 0.653(7) 0.585(6) 0.482 Uiso 1 1 d D U . . .
H2W2 H 0.643(10) 0.558(6) 0.494(5) 0.482 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.874(2) . ?
Cu1 N2 1.937(3) . ?
Cu1 N1 1.981(3) . ?
Cu1 N4 2.014(3) . ?
Cl1 C9 1.755(3) . ?
O1 C12 1.305(4) . ?
N1 C5 1.350(5) . ?
N1 C1 1.355(5) . ?
N2 C6 1.298(4) . ?
N2 N3 1.365(4) . ?
C6 C7 1.431(4) . ?
C6 H3 0.9300 . ?
N4 C13 1.334(4) . ?
N4 C14 1.336(4) . ?
C1 C2 1.364(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.373(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.401(5) . ?
C4 H4 0.9300 . ?
C5 N3 1.355(4) . ?
N3 H6 0.8600 . ?
C7 C8 1.396(4) . ?
C7 C12 1.423(5) . ?
C8 C9 1.374(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.391(5) . ?
C10 C11 1.363(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.415(5) . ?
C11 H11 0.9300 . ?
C13 C14 1.377(5) 2_557 ?
C13 H13 0.9300 . ?
C14 C13 1.377(5) 2_557 ?
C14 H14 0.9300 . ?
Cl2 O12 1.393(6) . ?
Cl2 O13 1.396(7) . ?
Cl2 O11 1.409(6) . ?
Cl2 O14 1.422(6) . ?
Cl2A O14A 1.368(12) . ?
Cl2A O12A 1.396(13) . ?
Cl2A O13A 1.405(12) . ?
Cl2A O11A 1.415(13) . ?
O1W H1W1 0.85(2) . ?
O1W H1W2 0.830(19) . ?
O2W H2W1 0.83(2) . ?
O2W H2W2 0.83(2) . ?

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 N2 92.67(10) . . ?
O1 Cu1 N1 174.58(11) . . ?
N2 Cu1 N1 82.00(11) . . ?
O1 Cu1 N4 85.79(11) . . ?
N2 Cu1 N4 176.90(11) . . ?
N1 Cu1 N4 99.59(12) . . ?
C12 O1 Cu1 128.3(2) . . ?
C5 N1 C1 118.3(3) . . ?
C5 N1 Cu1 111.8(2) . . ?
C1 N1 Cu1 129.8(3) . . ?
C6 N2 N3 119.1(3) . . ?
C6 N2 Cu1 128.0(2) . . ?
N3 N2 Cu1 112.9(2) . . ?
N2 C6 C7 123.3(3) . . ?
N2 C6 H3 118.4 . . ?
C7 C6 H3 118.4 . . ?
C13 N4 C14 116.8(3) . . ?
C13 N4 Cu1 117.8(2) . . ?
C14 N4 Cu1 125.2(2) . . ?
N1 C1 C2 122.4(4) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C1 C2 C3 118.9(4) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 120.7(4) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
C3 C4 C5 117.8(4) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
N1 C5 N3 116.8(3) . . ?
N1 C5 C4 121.8(3) . . ?
N3 C5 C4 121.4(3) . . ?
C5 N3 N2 116.4(3) . . ?
C5 N3 H6 121.8 . . ?
N2 N3 H6 121.8 . . ?
C8 C7 C12 119.6(3) . . ?
C8 C7 C6 117.4(3) . . ?
C12 C7 C6 123.0(3) . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.5(3) . . ?
C8 C9 Cl1 119.4(3) . . ?
C10 C9 Cl1 120.0(3) . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 121.8(3) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
O1 C12 C11 117.7(3) . . ?
O1 C12 C7 124.7(3) . . ?
C11 C12 C7 117.5(3) . . ?
N4 C13 C14 121.6(3) . 2_557 ?
N4 C13 H13 119.2 . . ?
C14 C13 H13 119.2 2_557 . ?
N4 C14 C13 121.6(3) . 2_557 ?
N4 C14 H14 119.2 . . ?
C13 C14 H14 119.2 2_557 . ?
O12 Cl2 O13 107.1(5) . . ?
O12 Cl2 O11 115.7(6) . . ?
O13 Cl2 O11 107.9(5) . . ?
O12 Cl2 O14 108.9(4) . . ?
O13 Cl2 O14 106.6(5) . . ?
O11 Cl2 O14 110.2(5) . . ?
O14A Cl2A O12A 111.2(11) . . ?
O14A Cl2A O13A 110.9(11) . . ?
O12A Cl2A O13A 107.8(10) . . ?
O14A Cl2A O11A 111.4(11) . . ?
O12A Cl2A O11A 108.2(10) . . ?
O13A Cl2A O11A 107.2(10) . . ?
H1W1 O1W H1W2 103(3) . . ?
H2W1 O2W H2W2 103(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Cu1 O1 C12 -1.6(3) . . . . ?
N4 Cu1 O1 C12 -178.9(3) . . . . ?
N3 N2 C6 C7 -178.8(3) . . . . ?
Cu1 N2 C6 C7 1.4(5) . . . . ?
C5 N1 C1 C2 -2.0(5) . . . . ?
Cu1 N1 C1 C2 175.8(3) . . . . ?
N1 C1 C2 C3 -0.2(6) . . . . ?
C1 C2 C3 C4 1.5(7) . . . . ?
C2 C3 C4 C5 -0.7(6) . . . . ?
C1 N1 C5 N3 -177.3(3) . . . . ?
Cu1 N1 C5 N3 4.6(4) . . . . ?
C1 N1 C5 C4 2.9(5) . . . . ?
Cu1 N1 C5 C4 -175.2(3) . . . . ?
C3 C4 C5 N1 -1.6(6) . . . . ?
C3 C4 C5 N3 178.6(4) . . . . ?
N1 C5 N3 N2 -3.9(5) . . . . ?
C4 C5 N3 N2 175.9(3) . . . . ?
C6 N2 N3 C5 -178.6(3) . . . . ?
Cu1 N2 N3 C5 1.2(4) . . . . ?
N2 C6 C7 C8 177.5(3) . . . . ?
N2 C6 C7 C12 -1.2(5) . . . . ?
C12 C7 C8 C9 0.3(5) . . . . ?
C6 C7 C8 C9 -178.4(3) . . . . ?
C7 C8 C9 C10 -0.5(5) . . . . ?
C7 C8 C9 Cl1 176.6(2) . . . . ?
C8 C9 C10 C11 0.1(5) . . . . ?
Cl1 C9 C10 C11 -176.9(3) . . . . ?
C9 C10 C11 C12 0.4(5) . . . . ?
Cu1 O1 C12 C11 -177.4(2) . . . . ?
Cu1 O1 C12 C7 2.1(5) . . . . ?
C10 C11 C12 O1 179.0(3) . . . . ?
C10 C11 C12 C7 -0.6(5) . . . . ?
C8 C7 C12 O1 -179.3(3) . . . . ?
C6 C7 C12 O1 -0.6(5) . . . . ?
C8 C7 C12 C11 0.2(5) . . . . ?
C6 C7 C12 C11 178.9(3) . . . . ?
C14 N4 C13 C14 0.6(6) . . . 2_557 ?
Cu1 N4 C13 C14 174.9(3) . . . 2_557 ?
C13 N4 C14 C13 -0.6(6) . . . 2_557 ?
Cu1 N4 C14 C13 -174.4(3) . . . 2_557 ?

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
C1 H1 O12 0.93 2.55 3.136(7) 121.5 1_545
C4 H4 O11A 0.93 2.53 3.388(19) 153.4 2_566
N3 H6 O1W 0.86 2.07 2.901(6) 161.3 .
C8 H8 O14 0.93 2.56 3.480(9) 169.8 .
C8 H8 O14A 0.93 2.41 3.296(19) 159.7 .
C13 H13 O14 0.93 2.38 3.182(8) 143.8 2_667
C13 H13 O14A 0.93 2.49 3.289(17) 144.7 2_667
C14 H14 Cl1 0.93 2.93 3.812(4) 159.9 2_567
O1W H1W1 O1W 0.85(2) 2.29(7) 2.793(10) 118(6) 2_566

_refine_diff_density_max         0.792
_refine_diff_density_min         -0.655
_refine_diff_density_rms         0.096

