# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_3
_database_code_depnum_ccdc_archive 'CCDC 1824713'
_audit_update_record             
;
2018-02-19 deposited with the CCDC.
2018-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 Cl Cu N2 O7'
_chemical_formula_weight         418.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu -1.9646 0.5888 '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'
O O 0.0492 0.0322 '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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.4852(2)
_cell_length_b                   14.3549(4)
_cell_length_c                   15.7193(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1463.38(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      18.90
_cell_measurement_theta_max      46.29

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.898
_exptl_crystal_F_000             844
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    4.223
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.341
_exptl_absorpt_correction_T_max  0.509
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       omega/2theta-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3279
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.171
_diffrn_reflns_theta_max         72.957
_diffrn_reflns_theta_full        67.500
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2908
_reflns_number_gt                2799
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_max     0.995
_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       'CAD4-Express Software (Nonius, 1994)'
_computing_cell_refinement       'CAD4-Express Software (Nonius, 1994)'
_computing_data_reduction        'GENHKL (Kretschmar, 1997)'
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1033P)²+1.2250P] 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 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.04(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2908
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1493
_refine_ls_wR_factor_gt          0.1471
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.128
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001

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
Cu Cu 0.87842(12) 0.68349(6) 0.61394(5) 0.0296(3) Uani 1 1 d . . . . .
O11 O 1.0265(7) 0.7428(3) 0.5176(3) 0.0328(9) Uani 1 1 d . . . . .
O12 O 1.1690(7) 0.8702(3) 0.4633(3) 0.0358(10) Uani 1 1 d . . . . .
O13 O 0.7462(7) 0.8432(3) 0.6063(3) 0.0383(10) Uani 1 1 d . . . . .
H13 H 0.661(16) 0.834(7) 0.568(6) 0.057 Uiso 1 1 d . U . . .
C11 C 1.0458(9) 0.8303(4) 0.5117(3) 0.0291(11) Uani 1 1 d . . . . .
C12 C 0.9090(10) 0.8920(4) 0.5669(4) 0.0345(13) Uani 1 1 d . . . . .
H12A H 0.993169 0.921001 0.610438 0.041 Uiso 1 1 calc R U . . .
H12B H 0.851556 0.941173 0.531817 0.041 Uiso 1 1 calc R U . . .
N1 N 1.0911(8) 0.7243(3) 0.7004(3) 0.0304(10) Uani 1 1 d . . . . .
N2 N 0.7461(8) 0.6257(3) 0.7151(3) 0.0304(10) Uani 1 1 d . . . . .
C1 C 1.2667(10) 0.7707(4) 0.6906(4) 0.0350(13) Uani 1 1 d . . . . .
H1 H 1.303612 0.790555 0.636435 0.042 Uiso 1 1 calc R U . . .
C2 C 1.3979(11) 0.7908(4) 0.7586(4) 0.0368(13) Uani 1 1 d . . . . .
H2 H 1.519876 0.823276 0.749304 0.044 Uiso 1 1 calc R U . . .
C3 C 1.3461(10) 0.7623(4) 0.8389(5) 0.0372(13) Uani 1 1 d . . . . .
H3 H 1.431229 0.776331 0.884742 0.045 Uiso 1 1 calc R U . . .
C4 C 1.1622(10) 0.7115(4) 0.8513(4) 0.0325(12) Uani 1 1 d . . . . .
C4N C 1.0390(9) 0.6945(4) 0.7797(4) 0.0299(11) Uani 1 1 d . . . . .
C5 C 1.0982(11) 0.6756(5) 0.9322(4) 0.0396(13) Uani 1 1 d . . . . .
H5 H 1.177435 0.687441 0.980269 0.048 Uiso 1 1 calc R U . . .
C6 C 0.9224(13) 0.6241(5) 0.9393(4) 0.0417(15) Uani 1 1 d . . . . .
H6 H 0.884244 0.600949 0.992269 0.050 Uiso 1 1 calc R U . . .
C7 C 0.7953(10) 0.6049(4) 0.8669(4) 0.0343(13) Uani 1 1 d . . . . .
C7N C 0.8546(10) 0.6415(4) 0.7872(4) 0.0295(11) Uani 1 1 d . . . . .
C8 C 0.6173(11) 0.5494(4) 0.8686(4) 0.0391(14) Uani 1 1 d . . . . .
H8 H 0.571486 0.523825 0.919615 0.047 Uiso 1 1 calc R U . . .
C9 C 0.5110(11) 0.5331(5) 0.7944(5) 0.0418(16) Uani 1 1 d . . . . .
H9 H 0.393470 0.495965 0.794922 0.050 Uiso 1 1 calc R U . . .
C10 C 0.5794(10) 0.5721(4) 0.7184(4) 0.0340(13) Uani 1 1 d . . . . .
H10 H 0.506551 0.560244 0.668572 0.041 Uiso 1 1 calc R U . . .
Cl Cl 1.0957(2) 0.45346(10) 0.62550(11) 0.0401(4) Uani 1 1 d . . . . .
O1 O 1.1126(11) 0.5485(4) 0.5956(5) 0.0705(19) Uani 1 1 d . . . . .
O4 O 1.2972(11) 0.4121(5) 0.6182(5) 0.078(2) Uani 1 1 d . . . . .
O2 O 1.0347(13) 0.4528(5) 0.7120(5) 0.077(2) Uani 1 1 d . . . . .
O3 O 0.9554(14) 0.4059(6) 0.5735(6) 0.091(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
Cu O12 1.978(5) 3_466 ?
Cu O11 1.985(4) . ?
Cu N2 1.989(5) . ?
Cu N1 2.022(5) . ?
Cu O13 2.450(5) . ?
Cu O1 2.479(6) . ?
O11 C11 1.266(8) . ?
O12 C11 1.243(8) . ?
O13 C12 1.411(7) . ?
C11 C12 1.524(8) . ?
N1 C1 1.328(8) . ?
N1 C4N 1.360(8) . ?
N2 C10 1.328(8) . ?
N2 C7N 1.353(8) . ?
C1 C2 1.396(10) . ?
C2 C3 1.368(9) . ?
C3 C4 1.412(9) . ?
C4 C4N 1.403(9) . ?
C4 C5 1.433(9) . ?
C4N C7N 1.422(8) . ?
C5 C6 1.363(11) . ?
C6 C7 1.432(10) . ?
C7 C8 1.403(10) . ?
C7 C7N 1.411(8) . ?
C8 C9 1.376(10) . ?
C9 C10 1.392(9) . ?
Cl O3 1.401(7) . ?
Cl O2 1.416(7) . ?
Cl O4 1.440(6) . ?
Cl O1 1.447(6) . ?

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
O12 Cu O11 91.75(19) 3_466 . ?
O12 Cu N2 91.8(2) 3_466 . ?
O11 Cu N2 176.3(2) . . ?
O12 Cu N1 173.36(19) 3_466 . ?
O11 Cu N1 93.4(2) . . ?
N2 Cu N1 83.0(2) . . ?
O12 Cu O13 95.41(17) 3_466 . ?
O11 Cu O13 74.40(17) . . ?
N2 Cu O13 106.15(18) . . ?
N1 Cu O13 90.05(18) . . ?
O12 Cu O1 92.6(2) 3_466 . ?
O11 Cu O1 87.1(2) . . ?
N2 Cu O1 91.8(2) . . ?
N1 Cu O1 83.5(2) . . ?
O13 Cu O1 160.06(18) . . ?
C11 O11 Cu 121.9(4) . . ?
C11 O12 Cu 129.6(4) . 3_566 ?
C12 O13 Cu 102.9(3) . . ?
O12 C11 O11 124.4(6) . . ?
O12 C11 C12 117.0(5) . . ?
O11 C11 C12 118.5(5) . . ?
O13 C12 C11 113.4(5) . . ?
C1 N1 C4N 118.4(6) . . ?
C1 N1 Cu 130.7(5) . . ?
C4N N1 Cu 110.8(4) . . ?
C10 N2 C7N 119.2(6) . . ?
C10 N2 Cu 128.6(5) . . ?
C7N N2 Cu 112.1(4) . . ?
N1 C1 C2 122.6(6) . . ?
C3 C2 C1 119.6(6) . . ?
C2 C3 C4 119.3(6) . . ?
C4N C4 C3 117.4(6) . . ?
C4N C4 C5 119.0(6) . . ?
C3 C4 C5 123.6(6) . . ?
N1 C4N C4 122.7(6) . . ?
N1 C4N C7N 117.0(5) . . ?
C4 C4N C7N 120.3(5) . . ?
C6 C5 C4 120.7(6) . . ?
C5 C6 C7 121.4(6) . . ?
C8 C7 C7N 117.0(6) . . ?
C8 C7 C6 124.6(6) . . ?
C7N C7 C6 118.5(6) . . ?
N2 C7N C7 122.6(6) . . ?
N2 C7N C4N 117.2(5) . . ?
C7 C7N C4N 120.2(6) . . ?
C9 C8 C7 119.5(6) . . ?
C8 C9 C10 120.0(6) . . ?
N2 C10 C9 121.7(6) . . ?
O3 Cl O2 112.1(6) . . ?
O3 Cl O4 110.0(6) . . ?
O2 Cl O4 109.1(5) . . ?
O3 Cl O1 108.6(5) . . ?
O2 Cl O1 109.8(5) . . ?
O4 Cl O1 107.1(5) . . ?
Cl O1 Cu 130.8(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 O3 0.93 2.55 3.261(10) 133.8 2_665
C10 H10 O12 0.93 2.53 3.030(8) 114.0 3_466
C12 H12B O1 0.97 2.54 3.309(10) 136.5 3_466
O13 H13 O11 0.82(10) 1.95(9) 2.710(7) 153(9) 3_466

_refine_diff_density_max         0.626
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.086

####################################################################### 
# 
# 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 1824714'
_audit_update_record             
;
2018-02-19 deposited with the CCDC.
2018-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H15 Cu N3 O6'
_chemical_formula_weight         384.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.3927(17)
_cell_length_b                   7.2489(12)
_cell_length_c                   11.1460(18)
_cell_angle_alpha                90
_cell_angle_beta                 116.460(2)
_cell_angle_gamma                90
_cell_volume                     751.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    730
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      26.16

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_F_000             394
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    1.491
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.765
_exptl_absorpt_correction_T_max  0.861
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4856
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.041
_diffrn_reflns_theta_max         27.993
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.742
_diffrn_reflns_point_group_measured_fraction_full 0.794
_reflns_number_total             2700
_reflns_number_gt                2416
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.429
_reflns_Friedel_fraction_max     0.483
_reflns_Friedel_fraction_full    0.558

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0260P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 656 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.017(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2700
_refine_ls_number_parameters     218
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0649
_refine_ls_wR_factor_gt          0.0633
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.001

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
Cu Cu 0.93352(4) 0.02632(6) 0.63086(4) 0.03107(12) Uani 1 1 d . . . . .
N1 N 0.7651(3) 0.1740(4) 0.6227(3) 0.0293(7) Uani 1 1 d . . . . .
N3 N 0.7670(3) 0.0263(6) 0.8127(3) 0.0333(6) Uani 1 1 d . . . . .
H3B H 0.756357 0.048517 0.883521 0.040 Uiso 1 1 calc R U . . .
N2 N 0.8998(3) -0.1681(4) 0.7364(3) 0.0296(7) Uani 1 1 d . . . . .
C1 C 0.7060(4) 0.3047(5) 0.5265(4) 0.0409(9) Uani 1 1 d . . . . .
H1 H 0.735135 0.310279 0.458857 0.049 Uiso 1 1 calc R U . . .
C2 C 0.6064(5) 0.4278(7) 0.5240(5) 0.0583(13) Uani 1 1 d . . . . .
H2 H 0.569104 0.516417 0.456827 0.070 Uiso 1 1 calc R U . . .
C3 C 0.5613(5) 0.4189(6) 0.6237(5) 0.0524(12) Uani 1 1 d . . . . .
H3 H 0.494660 0.503457 0.625076 0.063 Uiso 1 1 calc R U . . .
C4 C 0.6144(4) 0.2869(5) 0.7188(4) 0.0378(9) Uani 1 1 d . . . . .
H4 H 0.583673 0.278670 0.785223 0.045 Uiso 1 1 calc R U . . .
C5 C 0.7169(4) 0.1617(5) 0.7164(4) 0.0271(7) Uani 1 1 d . . . . .
C6 C 0.8318(4) -0.1404(5) 0.8128(4) 0.0283(8) Uani 1 1 d . . . . .
C7 C 0.8288(4) -0.2796(5) 0.9000(4) 0.0341(8) Uani 1 1 d . . . . .
H7 H 0.783627 -0.258363 0.954335 0.041 Uiso 1 1 calc R U . . .
C8 C 0.8926(4) -0.4459(5) 0.9041(4) 0.0369(9) Uani 1 1 d . . . . .
H8 H 0.889793 -0.539484 0.959983 0.044 Uiso 1 1 calc R U . . .
C9 C 0.9612(3) -0.4732(7) 0.8240(3) 0.0372(7) Uani 1 1 d . . . . .
H9 H 1.006258 -0.584894 0.826214 0.045 Uiso 1 1 calc R U . . .
C10 C 0.9621(4) -0.3352(5) 0.7424(4) 0.0337(8) Uani 1 1 d . . . . .
H10 H 1.007327 -0.355629 0.688005 0.040 Uiso 1 1 calc R U . . .
O11 O 0.9941(3) 0.2180(4) 0.5439(3) 0.0431(7) Uani 1 1 d . . . . .
O12 O 1.1782(3) 0.3842(4) 0.5547(3) 0.0393(7) Uani 1 1 d . . . . .
O13 O 1.1451(3) 0.0363(5) 0.7589(3) 0.0548(8) Uani 1 1 d . . . . .
H13 H 1.187001 -0.040296 0.833335 0.066 Uiso 1 1 calc R U . . .
C11 C 1.1249(4) 0.2655(5) 0.5988(4) 0.0306(8) Uani 1 1 d . . . . .
C12 C 1.2245(4) 0.1682(5) 0.7267(4) 0.0413(10) Uani 1 1 d . . . . .
H12A H 1.301360 0.107953 0.714738 0.050 Uiso 1 1 calc R U . . .
H12B H 1.267054 0.256957 0.798954 0.050 Uiso 1 1 calc R U . . .
O21 O 0.6514(3) 0.0193(5) -0.0052(3) 0.0465(6) Uani 1 1 d . . . . .
O22 O 0.7185(3) 0.3081(4) 0.0556(3) 0.0408(7) Uani 1 1 d . . . . .
O23 O 0.5629(3) 0.3189(4) 0.2026(3) 0.0454(7) Uani 1 1 d . . . . .
H23 H 0.504994 0.383546 0.142425 0.068 Uiso 1 1 calc R U . . .
C21 C 0.6563(4) 0.1630(5) 0.0601(4) 0.0319(8) Uani 1 1 d . . . . .
C22 C 0.5805(5) 0.1507(5) 0.1487(5) 0.0424(10) Uani 1 1 d . . . . .
H22A H 0.486298 0.096696 0.096842 0.051 Uiso 1 1 calc R U . . .
H22B H 0.634242 0.067221 0.222104 0.051 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
Cu O11 1.952(3) . ?
Cu N2 1.964(3) . ?
Cu N1 2.019(3) . ?
Cu O13 2.020(2) . ?
Cu O12 2.132(3) 2_746 ?
N1 C5 1.348(5) . ?
N1 C1 1.356(5) . ?
N3 C5 1.374(5) . ?
N3 C6 1.383(5) . ?
N2 C6 1.342(4) . ?
N2 C10 1.361(5) . ?
C1 C2 1.358(6) . ?
C2 C3 1.386(7) . ?
C3 C4 1.350(6) . ?
C4 C5 1.408(5) . ?
C6 C7 1.411(5) . ?
C7 C8 1.366(5) . ?
C8 C9 1.383(5) . ?
C9 C10 1.355(6) . ?
O11 C11 1.265(4) . ?
O12 C11 1.238(4) . ?
O13 C12 1.409(5) . ?
C11 C12 1.512(5) . ?
O21 C21 1.258(5) . ?
O22 C21 1.247(4) . ?
O23 C22 1.407(5) . ?
C21 C22 1.515(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 Cu N2 172.30(13) . . ?
O11 Cu N1 93.72(12) . . ?
N2 Cu N1 91.43(12) . . ?
O11 Cu O13 80.50(12) . . ?
N2 Cu O13 91.80(13) . . ?
N1 Cu O13 131.44(14) . . ?
O11 Cu O12 91.10(12) . 2_746 ?
N2 Cu O12 93.93(12) . 2_746 ?
N1 Cu O12 97.24(11) . 2_746 ?
O13 Cu O12 130.80(13) . 2_746 ?
C5 N1 C1 117.8(3) . . ?
C5 N1 Cu 123.0(2) . . ?
C1 N1 Cu 118.9(3) . . ?
C5 N3 C6 129.8(3) . . ?
C6 N2 C10 118.4(3) . . ?
C6 N2 Cu 123.9(2) . . ?
C10 N2 Cu 117.4(2) . . ?
N1 C1 C2 123.2(4) . . ?
C1 C2 C3 118.7(4) . . ?
C4 C3 C2 119.7(4) . . ?
C3 C4 C5 119.4(4) . . ?
N1 C5 N3 120.7(3) . . ?
N1 C5 C4 121.1(3) . . ?
N3 C5 C4 118.2(3) . . ?
N2 C6 N3 121.6(3) . . ?
N2 C6 C7 120.6(3) . . ?
N3 C6 C7 117.7(3) . . ?
C8 C7 C6 119.7(3) . . ?
C7 C8 C9 119.1(4) . . ?
C10 C9 C8 119.2(4) . . ?
C9 C10 N2 123.0(4) . . ?
C11 O11 Cu 117.9(2) . . ?
C11 O12 Cu 125.0(2) . 2_756 ?
C12 O13 Cu 114.9(2) . . ?
O12 C11 O11 124.9(3) . . ?
O12 C11 C12 117.3(3) . . ?
O11 C11 C12 117.8(3) . . ?
O13 C12 C11 108.9(3) . . ?
O22 C21 O21 124.3(3) . . ?
O22 C21 C22 120.3(3) . . ?
O21 C21 C22 115.4(3) . . ?
O23 C22 C21 115.6(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O23 H23 O21 0.82 1.93 2.747(4) 172.2 2_655
O13 H13 O22 0.93 1.62 2.532(4) 166.1 2_746
N3 H3B O21 0.86 2.00 2.782(3) 151.7 1_556
C7 H7 O21 0.93 2.59 3.309(5) 134.8 1_556
C12 H12A O23 0.97 2.46 3.219(5) 134.5 2_746

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 1824717'
_audit_update_record             
;
2018-02-19 deposited with the CCDC.
2018-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H13 Cu N3 O4'
_chemical_formula_weight         326.79

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.0214(12)
_cell_length_b                   18.010(3)
_cell_length_c                   19.735(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2495.7(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    942
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      25.73

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.740
_exptl_crystal_F_000             1336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    1.768
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.481
_exptl_absorpt_correction_T_max  0.588
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13769
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.064
_diffrn_reflns_theta_max         28.025
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2967
_reflns_number_gt                2480
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0361P)²+1.7530P] 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         2967
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.0943
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_restrained_S_all      1.157
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.002

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
Cu Cu 0.06289(5) 0.18326(2) 0.36018(2) 0.02522(11) Uani 1 1 d . . . . .
O11 O -0.0246(3) 0.19341(10) 0.26609(10) 0.0371(5) Uani 1 1 d . . . . .
O12 O -0.1505(3) 0.12587(11) 0.18292(9) 0.0354(5) Uani 1 1 d . . . . .
O13 O -0.0697(3) 0.09093(11) 0.35942(9) 0.0317(4) Uani 1 1 d . . . . .
C11 C -0.0977(4) 0.13416(15) 0.24285(14) 0.0277(6) Uani 1 1 d . . . . .
C12 C -0.1172(4) 0.07013(15) 0.29313(14) 0.0304(6) Uani 1 1 d . . . . .
H12A H -0.247386 0.052167 0.292426 0.036 Uiso 1 1 calc R U . . .
H12B H -0.034969 0.029697 0.279031 0.036 Uiso 1 1 calc R U . . .
N1 N 0.1491(3) 0.28823(12) 0.36161(10) 0.0257(5) Uani 1 1 d . . . . .
N3 N 0.0916(3) 0.30398(13) 0.47869(12) 0.0287(5) Uani 1 1 d . . . . .
N2 N 0.1139(3) 0.17473(12) 0.45916(11) 0.0270(5) Uani 1 1 d . . . . .
C1 C 0.2047(4) 0.31986(15) 0.30202(13) 0.0313(6) Uani 1 1 d . . . . .
H1 H 0.222142 0.289242 0.264588 0.038 Uiso 1 1 calc R U . . .
C2 C 0.2359(5) 0.39413(15) 0.29461(14) 0.0344(7) Uani 1 1 d . . . . .
H2 H 0.277461 0.413289 0.253424 0.041 Uiso 1 1 calc R U . . .
C3 C 0.2044(5) 0.44088(15) 0.34976(14) 0.0351(7) Uani 1 1 d . . . . .
H3 H 0.219101 0.491975 0.345373 0.042 Uiso 1 1 calc R U . . .
C4 C 0.1516(4) 0.41051(14) 0.41045(14) 0.0332(6) Uani 1 1 d . . . . .
H4 H 0.129474 0.440752 0.447824 0.040 Uiso 1 1 calc R U . . .
C5 C 0.1310(4) 0.33296(14) 0.41572(13) 0.0248(5) Uani 1 1 d . . . . .
C6 C 0.1076(4) 0.23236(14) 0.50254(13) 0.0248(5) Uani 1 1 d . . . . .
C7 C 0.1148(4) 0.22168(17) 0.57268(14) 0.0339(7) Uani 1 1 d . . . . .
H7 H 0.104591 0.261916 0.601989 0.041 Uiso 1 1 calc R U . . .
C8 C 0.1371(5) 0.15144(18) 0.59767(15) 0.0401(7) Uani 1 1 d . . . . .
H8 H 0.142642 0.143536 0.644197 0.048 Uiso 1 1 calc R U . . .
C9 C 0.1514(5) 0.09165(17) 0.55297(15) 0.0401(7) Uani 1 1 d . . . . .
H9 H 0.170130 0.043654 0.569024 0.048 Uiso 1 1 calc R U . . .
C10 C 0.1372(4) 0.10526(16) 0.48537(15) 0.0349(7) Uani 1 1 d . . . . .
H10 H 0.143658 0.065301 0.455616 0.042 Uiso 1 1 calc R U . . .
O1W O 0.5986(4) 0.08678(14) 0.42301(11) 0.0394(5) Uani 1 1 d . . . . .
H1B H 0.698(6) 0.087(2) 0.4069(19) 0.051(12) Uiso 1 1 d . . . . .
H3B H 0.088(4) 0.3319(17) 0.5083(17) 0.032(9) Uiso 1 1 d . . . . .
H1A H 0.524(6) 0.094(2) 0.396(2) 0.049(12) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu O13 1.9058(19) . ?
Cu O11 1.964(2) . ?
Cu N1 1.985(2) . ?
Cu N2 1.992(2) . ?
Cu O12 2.417(2) 6_656 ?
O11 C11 1.270(3) . ?
O12 C11 1.248(3) . ?
O13 C12 1.401(3) . ?
C11 C12 1.528(4) . ?
N1 C5 1.344(3) . ?
N1 C1 1.364(3) . ?
N3 C5 1.376(3) . ?
N3 C6 1.378(3) . ?
N2 C6 1.346(3) . ?
N2 C10 1.364(3) . ?
C1 C2 1.363(4) . ?
C2 C3 1.394(4) . ?
C3 C4 1.368(4) . ?
C4 C5 1.408(4) . ?
C6 C7 1.399(4) . ?
C7 C8 1.367(4) . ?
C8 C9 1.396(4) . ?
C9 C10 1.360(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
O13 Cu O11 85.47(8) . . ?
O13 Cu N1 168.51(9) . . ?
O11 Cu N1 91.16(8) . . ?
O13 Cu N2 91.61(8) . . ?
O11 Cu N2 172.05(9) . . ?
N1 Cu N2 90.27(9) . . ?
O13 Cu O12 91.76(8) . 6_656 ?
O11 Cu O12 88.14(8) . 6_656 ?
N1 Cu O12 99.12(8) . 6_656 ?
N2 Cu O12 99.35(8) . 6_656 ?
C11 O11 Cu 112.93(17) . . ?
C11 O12 Cu 121.97(17) . 6_556 ?
C12 O13 Cu 110.91(16) . . ?
O12 C11 O11 124.2(3) . . ?
O12 C11 C12 119.9(2) . . ?
O11 C11 C12 115.8(2) . . ?
O13 C12 C11 112.5(2) . . ?
C5 N1 C1 117.5(2) . . ?
C5 N1 Cu 123.61(18) . . ?
C1 N1 Cu 118.21(17) . . ?
C5 N3 C6 130.3(2) . . ?
C6 N2 C10 118.0(2) . . ?
C6 N2 Cu 123.93(18) . . ?
C10 N2 Cu 117.67(19) . . ?
C2 C1 N1 123.3(3) . . ?
C1 C2 C3 118.9(3) . . ?
C4 C3 C2 119.0(2) . . ?
C3 C4 C5 119.3(2) . . ?
N1 C5 N3 120.6(2) . . ?
N1 C5 C4 121.8(2) . . ?
N3 C5 C4 117.6(2) . . ?
N2 C6 N3 120.5(2) . . ?
N2 C6 C7 121.5(2) . . ?
N3 C6 C7 118.0(2) . . ?
C8 C7 C6 119.3(3) . . ?
C7 C8 C9 119.6(3) . . ?
C10 C9 C8 118.4(3) . . ?
C9 C10 N2 123.1(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
C10 H10 O13 0.93 2.46 2.890(3) 108.2 .
C3 H3 O12 0.93 2.52 3.415(3) 161.0 3
C1 H1 O11 0.93 2.55 3.257(4) 133.0 6_656
C1 H1 O11 0.93 2.45 2.878(3) 108.4 .
O1W H1A O12 0.76(4) 2.07(4) 2.815(3) 171(4) 6_656
N3 H3B O1W 0.77(3) 2.00(3) 2.764(3) 172(3) 4_456
O1W H1B O13 0.77(4) 1.88(4) 2.647(3) 174(4) 1_655

_refine_diff_density_max         0.371
_refine_diff_density_min         -0.509
_refine_diff_density_rms         0.119

####################################################################### 
# 
# 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 1824715'
_audit_update_record             
;
2018-02-19 deposited with the CCDC.
2018-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H11 Cl Cu N2 O7'
_chemical_formula_weight         394.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 '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'
O O 0.0106 0.0060 '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'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.5406(13)
_cell_length_b                   14.063(3)
_cell_length_c                   15.063(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1385.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2.705
_cell_measurement_theta_max      26.25


_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.890
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             796
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    1.810
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.729
_exptl_absorpt_correction_T_max  0.805
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART CCD-1000'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2837
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         1.981
_diffrn_reflns_theta_max         26.387
_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             2837
_reflns_number_gt                2672
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_max     0.999
_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       SMART
_computing_cell_refinement       SAINT
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXS
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0283P)²+0.3172P] 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 
;
 Flack x determined using 1084 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2837
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0213
_refine_ls_wR_factor_ref         0.0561
_refine_ls_wR_factor_gt          0.0547
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.002

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
Cu Cu 0.90311(5) 0.83256(2) 0.38770(2) 0.02526(11) Uani 1 1 d . . . . .
Cl Cl 1.10361(16) 1.06803(6) 0.40093(5) 0.0416(2) Uani 1 1 d . . . . .
O1 O 1.1214(4) 0.96934(18) 0.42558(19) 0.0511(7) Uani 1 1 d . . . . .
O2 O 1.2945(7) 1.1109(3) 0.4210(3) 0.1033(15) Uani 1 1 d . . . . .
O3 O 0.9474(8) 1.1097(3) 0.4505(3) 0.1098(18) Uani 1 1 d . . . . .
O4 O 1.0627(6) 1.0761(2) 0.30832(18) 0.0667(9) Uani 1 1 d . . . . .
O11 O 1.0552(3) 0.76154(15) 0.47987(13) 0.0285(5) Uani 1 1 d . . . . .
O12 O 1.1960(4) 0.62519(15) 0.52403(14) 0.0306(5) Uani 1 1 d . . . . .
O13 O 0.7712(3) 0.66994(17) 0.38130(15) 0.0309(5) Uani 1 1 d . . . . .
H13 H 0.696(7) 0.671(3) 0.420(3) 0.057(14) Uiso 1 1 d . . . . .
N2 N 0.7611(4) 0.89799(19) 0.28958(17) 0.0258(5) Uani 1 1 d . . . . .
N1 N 1.1022(4) 0.80167(17) 0.29040(16) 0.0272(5) Uani 1 1 d . . . . .
C10 C 0.5932(5) 0.9511(2) 0.2967(2) 0.0317(7) Uani 1 1 d . . . . .
H10 H 0.535920 0.960364 0.352530 0.038 Uiso 1 1 calc R U . . .
C9 C 0.5012(5) 0.9930(2) 0.2239(2) 0.0357(8) Uani 1 1 d . . . . .
H9 H 0.384963 1.030490 0.230458 0.043 Uiso 1 1 calc R U . . .
C8 C 0.5861(6) 0.9779(2) 0.1412(2) 0.0373(7) Uani 1 1 d . . . . .
H8 H 0.526650 1.004999 0.091159 0.045 Uiso 1 1 calc R U . . .
C7 C 0.7592(5) 0.9225(2) 0.1328(2) 0.0348(8) Uani 1 1 d . . . . .
H7 H 0.816343 0.911030 0.077279 0.042 Uiso 1 1 calc R U . . .
C6 C 0.8461(4) 0.8844(2) 0.2089(2) 0.0263(7) Uani 1 1 d . . . . .
C5 C 1.0401(4) 0.8298(2) 0.2094(2) 0.0269(6) Uani 1 1 d . . . . .
C4 C 1.1538(5) 0.8108(2) 0.1339(2) 0.0355(8) Uani 1 1 d . . . . .
H4 H 1.107556 0.830637 0.078535 0.043 Uiso 1 1 calc R U . . .
C3 C 1.3369(5) 0.7622(3) 0.1416(2) 0.0388(8) Uani 1 1 d . . . . .
H3 H 1.414277 0.748098 0.091520 0.047 Uiso 1 1 calc R U . . .
C2 C 1.4027(6) 0.7349(2) 0.2251(2) 0.0367(7) Uani 1 1 d . . . . .
H2 H 1.525966 0.702822 0.232307 0.044 Uiso 1 1 calc R U . . .
C1 C 1.2821(5) 0.7562(2) 0.2974(2) 0.0335(7) Uani 1 1 d . . . . .
H1 H 1.327209 0.738322 0.353488 0.040 Uiso 1 1 calc R U . . .
C11 C 1.0717(4) 0.6717(2) 0.47810(17) 0.0239(6) Uani 1 1 d . . . . .
C12 C 0.9347(5) 0.6150(2) 0.4160(2) 0.0287(7) Uani 1 1 d . . . . .
H12A H 1.016158 0.590807 0.367156 0.034 Uiso 1 1 calc R U . . .
H12B H 0.879071 0.560988 0.447860 0.034 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
Cu N2 1.973(3) . ?
Cu O11 1.979(2) . ?
Cu O12 1.989(2) 3_466 ?
Cu N1 2.008(3) . ?
Cu O13 2.446(2) . ?
Cu O1 2.463(3) . ?
Cl O3 1.395(4) . ?
Cl O2 1.419(4) . ?
Cl O4 1.425(3) . ?
Cl O1 1.441(3) . ?
O11 C11 1.269(4) . ?
O12 C11 1.252(4) . ?
O13 C12 1.418(4) . ?
N2 C10 1.333(4) . ?
N2 C6 1.350(4) . ?
N1 C1 1.343(4) . ?
N1 C5 1.345(4) . ?
C10 C9 1.383(4) . ?
C9 C8 1.380(5) . ?
C8 C7 1.380(5) . ?
C7 C6 1.388(4) . ?
C6 C5 1.483(4) . ?
C5 C4 1.385(4) . ?
C4 C3 1.384(5) . ?
C3 C2 1.384(5) . ?
C2 C1 1.377(5) . ?
C11 C12 1.521(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu O11 176.05(10) . . ?
N2 Cu O12 92.35(10) . 3_466 ?
O11 Cu O12 91.37(9) . 3_466 ?
N2 Cu N1 81.92(11) . . ?
O11 Cu N1 94.42(10) . . ?
O12 Cu N1 173.82(9) 3_466 . ?
N2 Cu O13 103.91(9) . . ?
O11 Cu O13 74.51(8) . . ?
O12 Cu O13 93.75(9) 3_466 . ?
N1 Cu O13 89.87(9) . . ?
N2 Cu O1 94.72(10) . . ?
O11 Cu O1 86.57(9) . . ?
O12 Cu O1 90.38(9) 3_466 . ?
N1 Cu O1 87.83(10) . . ?
O13 Cu O1 160.71(8) . . ?
O3 Cl O2 110.6(3) . . ?
O3 Cl O4 110.7(2) . . ?
O2 Cl O4 109.9(2) . . ?
O3 Cl O1 109.0(2) . . ?
O2 Cl O1 106.4(2) . . ?
O4 Cl O1 110.15(18) . . ?
Cl O1 Cu 130.21(17) . . ?
C11 O11 Cu 122.08(18) . . ?
C11 O12 Cu 131.0(2) . 3_566 ?
C12 O13 Cu 103.21(16) . . ?
C10 N2 C6 119.4(3) . . ?
C10 N2 Cu 126.1(2) . . ?
C6 N2 Cu 114.5(2) . . ?
C1 N1 C5 118.4(3) . . ?
C1 N1 Cu 127.9(2) . . ?
C5 N1 Cu 113.7(2) . . ?
N2 C10 C9 122.3(3) . . ?
C8 C9 C10 118.3(3) . . ?
C7 C8 C9 120.0(3) . . ?
C8 C7 C6 118.6(3) . . ?
N2 C6 C7 121.3(3) . . ?
N2 C6 C5 114.9(3) . . ?
C7 C6 C5 123.7(3) . . ?
N1 C5 C4 121.7(3) . . ?
N1 C5 C6 114.6(3) . . ?
C4 C5 C6 123.7(3) . . ?
C3 C4 C5 119.4(3) . . ?
C4 C3 C2 118.9(3) . . ?
C1 C2 C3 118.7(3) . . ?
N1 C1 C2 122.9(3) . . ?
O12 C11 O11 124.3(3) . . ?
O12 C11 C12 116.7(3) . . ?
O11 C11 C12 119.0(3) . . ?
O13 C12 C11 112.7(2) . . ?

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
C7 H7 O3 0.93 2.59 3.093(5) 114.5 2_674
C9 H9 O4 0.93 2.50 3.348(5) 152.4 1_455
C10 H10 O12 0.93 2.45 2.983(4) 116.5 3_466
O13 H13 O11 0.76(4) 2.00(4) 2.702(3) 152(5) 3_466
C12 H12B O1 0.97 2.58 3.362(4) 137.8 3_466

_refine_diff_density_max         0.319
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_32016401_0m
_database_code_depnum_ccdc_archive 'CCDC 1824716'
_audit_update_record             
;
2018-02-19 deposited with the CCDC.
2018-03-26 downloaded from the CCDC.
;
_audit_creation_date             2017-10-30
_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 H14 Cu N3 O4, Cl O4'
_chemical_formula_sum            'C12 H14 Cl Cu N3 O8'
_chemical_formula_weight         427.25
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   10.2071(6)
_cell_length_b                   9.4026(5)
_cell_length_c                   16.5141(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.226(2)
_cell_angle_gamma                90
_cell_volume                     1584.55(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   0.830
_shelx_estimated_absorpt_T_min   0.709
_exptl_absorpt_coefficient_mu    1.596
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             868
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.121
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23261
_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         28.364
_diffrn_reflns_theta_min         2.369
_diffrn_ambient_temperature      100.0
_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 Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Incoatec high brillance I\muS microsource'
_diffrn_radiation_monochromator  'Incoatec HeliosTM multilayer optics'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3639
_reflns_number_total             3966
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3966
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0236
_refine_ls_restrained_S_all      1.075
_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)+(0.0286P)²+1.2685P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0600
_refine_ls_wR_factor_ref         0.0616
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3A), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
Cu Cu 0.28264(2) 0.22401(2) 0.41045(2) 0.00871(6) Uani 1 1 d . . . . .
O11 O 0.25506(10) 0.34486(11) 0.31577(6) 0.0088(2) Uani 1 1 d . . . . .
O12 O 0.16641(10) 0.35843(11) 0.19176(6) 0.0112(2) Uani 1 1 d . . . . .
O13 O 0.18561(11) 0.07691(11) 0.33623(6) 0.0107(2) Uani 1 1 d . . . . .
C11 C 0.19047(14) 0.29292(15) 0.25631(8) 0.0087(3) Uani 1 1 d . . . . .
C12 C 0.13848(15) 0.14295(16) 0.26354(8) 0.0120(3) Uani 1 1 d . . . . .
H12A H 0.041501 0.145179 0.263258 0.014 Uiso 1 1 calc R . . . .
H12B H 0.166120 0.086382 0.216318 0.014 Uiso 1 1 calc R . . . .
O1W O 0.09906(11) 0.31029(13) 0.44799(7) 0.0148(2) Uani 1 1 d . . . . .
N1 N 0.46328(12) 0.29632(13) 0.43187(7) 0.0088(2) Uani 1 1 d . . . . .
N2 N 0.28734(12) 0.09833(14) 0.50532(7) 0.0105(2) Uani 1 1 d . . . . .
N3 N 0.48387(13) 0.19185(14) 0.56263(8) 0.0121(2) Uani 1 1 d . . . . .
C1 C 0.52003(15) 0.37620(16) 0.37349(9) 0.0117(3) Uani 1 1 d . . . . .
H1 H 0.474712 0.387085 0.323026 0.014 Uiso 1 1 calc R . . . .
C2 C 0.63919(15) 0.44172(17) 0.38376(9) 0.0150(3) Uani 1 1 d . . . . .
H2 H 0.675358 0.496823 0.341515 0.018 Uiso 1 1 calc R . . . .
C3 C 0.70614(15) 0.42554(17) 0.45783(9) 0.0149(3) Uani 1 1 d . . . . .
H3A H 0.787832 0.471736 0.467229 0.018 Uiso 1 1 calc R . . . .
C4 C 0.65294(14) 0.34248(17) 0.51676(9) 0.0132(3) Uani 1 1 d . . . . .
H4 H 0.697903 0.329158 0.567155 0.016 Uiso 1 1 calc R . . . .
C5 C 0.53086(14) 0.27712(15) 0.50175(8) 0.0093(3) Uani 1 1 d . . . . .
C6 C 0.37722(14) 0.10318(16) 0.56567(8) 0.0098(3) Uani 1 1 d . . . . .
C7 C 0.36676(15) 0.01759(17) 0.63550(9) 0.0136(3) Uani 1 1 d . . . . .
H7 H 0.431923 0.022004 0.677370 0.016 Uiso 1 1 calc R . . . .
C8 C 0.26203(16) -0.07155(17) 0.64218(9) 0.0150(3) Uani 1 1 d . . . . .
H8 H 0.253567 -0.129768 0.688794 0.018 Uiso 1 1 calc R . . . .
C9 C 0.16715(16) -0.07644(18) 0.57975(9) 0.0164(3) Uani 1 1 d . . . . .
H9 H 0.093023 -0.137016 0.583408 0.020 Uiso 1 1 calc R . . . .
C10 C 0.18383(15) 0.00824(17) 0.51326(9) 0.0145(3) Uani 1 1 d . . . . .
H10 H 0.120069 0.003948 0.470575 0.017 Uiso 1 1 calc R . . . .
Cl Cl 0.02135(3) 0.36399(4) 0.66063(2) 0.01342(8) Uani 1 1 d . . . . .
O1 O -0.04822(12) 0.32393(17) 0.58651(7) 0.0285(3) Uani 1 1 d . . . . .
O2 O 0.14492(12) 0.29211(14) 0.66541(8) 0.0266(3) Uani 1 1 d . . . . .
O3 O -0.05734(13) 0.33049(14) 0.72821(7) 0.0227(3) Uani 1 1 d . . . . .
O4 O 0.04481(12) 0.51636(13) 0.65921(7) 0.0217(3) Uani 1 1 d . . . . .
H1WA H 0.066(2) 0.367(3) 0.4188(14) 0.027(6) Uiso 1 1 d . . . . .
H1WB H 0.065(2) 0.307(2) 0.4881(15) 0.026(6) Uiso 1 1 d . . . . .
H13 H 0.238(2) 0.011(3) 0.3250(15) 0.040(7) Uiso 1 1 d . . . . .
H3 H 0.532(2) 0.186(2) 0.6004(12) 0.014(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu O11 1.9484(10) . ?
Cu O13 2.0843(10) . ?
Cu O1W 2.1456(12) . ?
Cu N1 1.9898(12) . ?
Cu N2 1.9621(12) . ?
O11 C11 1.2686(17) . ?
O12 C11 1.2510(17) . ?
O13 C12 1.4260(16) . ?
C11 C12 1.512(2) . ?
N1 C1 1.3612(19) . ?
N1 C5 1.3438(18) . ?
N2 C6 1.3409(18) . ?
N2 C10 1.3628(19) . ?
N3 C5 1.3800(19) . ?
N3 C6 1.3729(19) . ?
C1 C2 1.371(2) . ?
C2 C3 1.397(2) . ?
C3 C4 1.369(2) . ?
C4 C5 1.407(2) . ?
C6 C7 1.4122(19) . ?
C7 C8 1.365(2) . ?
C8 C9 1.400(2) . ?
C9 C10 1.370(2) . ?
Cl O1 1.4516(12) . ?
Cl O2 1.4317(13) . ?
Cl O3 1.4242(12) . ?
Cl O4 1.4528(13) . ?

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
O11 Cu O13 81.75(4) . . ?
O11 Cu O1W 84.22(4) . . ?
O11 Cu N1 93.49(5) . . ?
O11 Cu N2 173.03(5) . . ?
O13 Cu O1W 90.80(5) . . ?
N1 Cu O13 139.30(5) . . ?
N1 Cu O1W 129.13(5) . . ?
N2 Cu O13 94.19(5) . . ?
N2 Cu O1W 90.21(5) . . ?
N2 Cu N1 93.27(5) . . ?
C11 O11 Cu 117.41(9) . . ?
C12 O13 Cu 110.70(8) . . ?
O11 C11 C12 118.38(12) . . ?
O12 C11 O11 124.00(13) . . ?
O12 C11 C12 117.62(12) . . ?
O13 C12 C11 111.09(11) . . ?
C1 N1 Cu 117.99(10) . . ?
C5 N1 Cu 124.29(10) . . ?
C5 N1 C1 117.64(12) . . ?
C6 N2 Cu 125.29(10) . . ?
C6 N2 C10 117.98(12) . . ?
C10 N2 Cu 116.45(10) . . ?
C6 N3 C5 131.89(13) . . ?
N1 C1 C2 123.38(13) . . ?
C1 C2 C3 118.40(14) . . ?
C4 C3 C2 119.38(14) . . ?
C3 C4 C5 119.16(14) . . ?
N1 C5 N3 121.58(13) . . ?
N1 C5 C4 121.95(13) . . ?
N3 C5 C4 116.48(13) . . ?
N2 C6 N3 121.59(13) . . ?
N2 C6 C7 121.68(13) . . ?
N3 C6 C7 116.73(13) . . ?
C8 C7 C6 119.28(13) . . ?
C7 C8 C9 119.43(14) . . ?
C10 C9 C8 118.38(14) . . ?
N2 C10 C9 123.26(14) . . ?
O1 Cl O4 108.67(8) . . ?
O2 Cl O1 109.79(8) . . ?
O2 Cl O4 108.73(8) . . ?
O3 Cl O1 109.24(8) . . ?
O3 Cl O2 111.30(8) . . ?
O3 Cl O4 109.07(8) . . ?

_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_4
_database_code_depnum_ccdc_archive 'CCDC 1824718'
_audit_update_record             
;
2018-02-19 deposited with the CCDC.
2018-03-26 downloaded from the CCDC.
;
_audit_creation_date             2017-11-02
_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         'C22 H22 Cu2 N6 O4, 2(Cl O4), 2(H2 O)'
_chemical_formula_sum            'C22 H26 Cl2 Cu2 N6 O14'
_chemical_formula_weight         796.47
_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        'P 1 21/c 1'
_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                   13.1280(9)
_cell_length_b                   8.7729(6)
_cell_length_c                   25.0767(16)
_cell_angle_alpha                90
_cell_angle_beta                 90.356(2)
_cell_angle_gamma                90
_cell_volume                     2888.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      2.25
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.664
_exptl_absorpt_coefficient_mu    1.739
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1381 before and 0.0539 after correction.
The Ratio of minimum to maximum transmission is 0.8937.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.022
_exptl_crystal_size_min          0.021
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            36559
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.416
_diffrn_reflns_theta_min         2.253
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Incoatec high brillance I\muS microsource'
_diffrn_radiation_monochromator  'Incoatec HeliosTM multilayer optics'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4637
_reflns_number_total             5908
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.329
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     459
_refine_ls_number_reflns         5908
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.038
_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)+(0.0292P)²+5.9965P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0819
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 O3W-H3WB
 0.85 with sigma of 0.02
 O3W-H3WA
 0.85 with sigma of 0.02
 O2W-H2WA
 0.85 with sigma of 0.02
 O2W-H2WB
 0.85 with sigma of 0.02
 O1W-H1WA
 0.85 with sigma of 0.02
 O1W-H1WB
 0.85 with sigma of 0.02
 N3-H3
 0.87 with sigma of 0.02
 N6-H6
 0.87 with sigma of 0.02
3. Others
 Fixed Sof: O1A(0.85) O1B(0.15) O2A(0.85) O2B(0.15) O3A(0.85) O3B(0.15)
4.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
4.b Aromatic/amide H refined with riding coordinates:
 C101(H101), C102(H102), C103(H103), C104(H104), C107(H107), C108(H108),
 C109(H109), C110(H110), C111(H111), C112(H112), C113(H113), C114(H114),
 C117(H117), C118(H118), C119(H119), C120(H120)
;
_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 0.29653(3) 0.13520(4) 0.72644(2) 0.00700(9) Uani 1 1 d . . . . .
Cu2 Cu 0.45230(3) 0.35515(4) 0.64331(2) 0.00859(10) Uani 1 1 d . . . . .
Cl1 Cl 0.66947(6) 0.09025(9) 0.63416(3) 0.01504(17) Uani 1 1 d . . . . .
Cl2 Cl 0.14714(6) 0.47606(9) 0.41555(3) 0.01568(17) Uani 1 1 d . . . . .
O1W O 0.27652(18) 0.2225(3) 0.80850(9) 0.0156(5) Uani 1 1 d D . . . .
H1WA H 0.308(3) 0.298(3) 0.8198(14) 0.021(10) Uiso 1 1 d D . . . .
H1WB H 0.233(3) 0.201(5) 0.8319(14) 0.043(14) Uiso 1 1 d D . . . .
O1A O 0.6030(2) 0.2017(4) 0.61166(12) 0.0214(7) Uani 0.85 1 d . . P A 1
O1B O 0.6272(12) 0.2415(18) 0.6349(6) 0.010(3) Uiso 0.15 1 d . . P A 2
O2W O -0.05206(19) 0.0668(3) 0.57128(10) 0.0233(6) Uani 1 1 d D . . . .
H2WA H -0.044(4) 0.148(4) 0.5529(18) 0.057(16) Uiso 1 1 d D . . . .
H2WB H -0.1113(19) 0.089(5) 0.5810(17) 0.046(14) Uiso 1 1 d D . . . .
O2A O 0.7330(2) 0.0251(4) 0.59489(14) 0.0315(8) Uani 0.85 1 d . . P A 1
O2B O 0.6814(12) 0.0555(18) 0.5729(6) 0.015(3) Uiso 0.15 1 d . . P A 2
O3W O -0.0337(2) 0.1991(3) 0.47404(11) 0.0308(6) Uani 1 1 d D . . . .
H3WA H 0.002(4) 0.131(5) 0.457(2) 0.08(2) Uiso 1 1 d D . . . .
H3WB H 0.001(4) 0.284(4) 0.471(2) 0.068(18) Uiso 1 1 d D . . . .
O3A O 0.7270(2) 0.1531(4) 0.67771(12) 0.0341(8) Uani 0.85 1 d . . P A 1
O3B O 0.7749(11) 0.0898(17) 0.6525(6) 0.014(3) Uiso 0.15 1 d . . P A 2
O4 O 0.60565(17) -0.0288(3) 0.65682(10) 0.0220(6) Uani 1 1 d . . . . .
O5 O 0.0856(2) 0.4685(3) 0.46233(11) 0.0418(8) Uani 1 1 d . . . . .
O6 O 0.2489(2) 0.4281(4) 0.42800(12) 0.0407(8) Uani 1 1 d . . . . .
O7 O 0.1463(2) 0.6284(3) 0.39632(11) 0.0372(7) Uani 1 1 d . . . . .
O8 O 0.10610(19) 0.3750(3) 0.37556(10) 0.0292(6) Uani 1 1 d . . . . .
O11 O 0.54451(16) 0.4665(2) 0.68989(8) 0.0132(5) Uani 1 1 d . . . . .
O12 O 0.62702(15) 0.4411(2) 0.76772(8) 0.0096(4) Uani 1 1 d . . . . .
O13 O 0.42149(15) 0.2422(2) 0.70754(8) 0.0095(4) Uani 1 1 d . . . . .
N1 N 0.45468(19) 0.5148(3) 0.58719(10) 0.0101(5) Uani 1 1 d . . . . .
N2 N 0.37205(18) 0.2163(3) 0.59774(10) 0.0097(5) Uani 1 1 d . . . . .
N3 N 0.3169(2) 0.4081(3) 0.53825(10) 0.0138(6) Uani 1 1 d D . . . .
H3 H 0.281(2) 0.423(4) 0.5108(11) 0.025(10) Uiso 1 1 d D . . . .
N4 N 0.21587(18) 0.3059(3) 0.69373(10) 0.0100(5) Uani 1 1 d . . . . .
N5 N 0.16912(18) 0.0131(3) 0.72751(10) 0.0087(5) Uani 1 1 d . . . . .
N6 N 0.10156(19) 0.1356(3) 0.65137(10) 0.0120(6) Uani 1 1 d D . . . .
H6 H 0.060(3) 0.127(5) 0.6254(12) 0.033(11) Uiso 1 1 d D . . . .
C11 C 0.5626(2) 0.3983(3) 0.73353(12) 0.0089(6) Uani 1 1 d . . . . .
C12 C 0.5025(2) 0.2558(3) 0.74503(12) 0.0087(6) Uani 1 1 d . . . . .
H12A H 0.547476 0.165580 0.742680 0.010 Uiso 1 1 calc R . . . .
H12B H 0.474669 0.260669 0.781596 0.010 Uiso 1 1 calc R . . . .
C101 C 0.5252(2) 0.6279(4) 0.59124(12) 0.0139(7) Uani 1 1 d . . . . .
H101 H 0.572384 0.624110 0.620079 0.017 Uiso 1 1 calc R . . . .
C102 C 0.5320(3) 0.7469(4) 0.55612(12) 0.0160(7) Uani 1 1 d . . . . .
H102 H 0.583148 0.822766 0.560206 0.019 Uiso 1 1 calc R . . . .
C103 C 0.4619(2) 0.7537(4) 0.51415(12) 0.0157(7) Uani 1 1 d . . . . .
H103 H 0.463608 0.835771 0.489471 0.019 Uiso 1 1 calc R . . . .
C104 C 0.3905(2) 0.6408(4) 0.50890(12) 0.0150(7) Uani 1 1 d . . . . .
H104 H 0.342391 0.643817 0.480486 0.018 Uiso 1 1 calc R . . . .
C105 C 0.3891(2) 0.5210(4) 0.54572(12) 0.0128(7) Uani 1 1 d . . . . .
C106 C 0.3145(2) 0.2599(4) 0.55628(12) 0.0124(7) Uani 1 1 d . . . . .
C107 C 0.2492(2) 0.1574(4) 0.52957(13) 0.0174(7) Uani 1 1 d . . . . .
H107 H 0.207889 0.191125 0.500674 0.021 Uiso 1 1 calc R . . . .
C108 C 0.2462(2) 0.0093(4) 0.54573(13) 0.0185(8) Uani 1 1 d . . . . .
H108 H 0.202137 -0.061175 0.528381 0.022 Uiso 1 1 calc R . . . .
C109 C 0.3084(2) -0.0385(4) 0.58812(13) 0.0157(7) Uani 1 1 d . . . . .
H109 H 0.307981 -0.141623 0.599702 0.019 Uiso 1 1 calc R . . . .
C110 C 0.3699(2) 0.0669(4) 0.61242(12) 0.0121(7) Uani 1 1 d . . . . .
H110 H 0.413003 0.034450 0.640798 0.014 Uiso 1 1 calc R . . . .
C111 C 0.2485(2) 0.4514(4) 0.70088(13) 0.0133(7) Uani 1 1 d . . . . .
H111 H 0.296678 0.471115 0.728447 0.016 Uiso 1 1 calc R . . . .
C112 C 0.2154(3) 0.5711(4) 0.67033(14) 0.0195(8) Uani 1 1 d . . . . .
H112 H 0.239037 0.671830 0.676756 0.023 Uiso 1 1 calc R . . . .
C113 C 0.1454(3) 0.5400(4) 0.62914(14) 0.0214(8) Uani 1 1 d . . . . .
H113 H 0.123738 0.619223 0.605868 0.026 Uiso 1 1 calc R . . . .
C114 C 0.1086(2) 0.3959(4) 0.62266(13) 0.0177(7) Uani 1 1 d . . . . .
H114 H 0.059875 0.374344 0.595524 0.021 Uiso 1 1 calc R . . . .
C115 C 0.1434(2) 0.2801(4) 0.65644(12) 0.0118(7) Uani 1 1 d . . . . .
C116 C 0.0980(2) 0.0207(4) 0.68866(12) 0.0104(6) Uani 1 1 d . . . . .
C117 C 0.0192(2) -0.0879(4) 0.68538(13) 0.0158(7) Uani 1 1 d . . . . .
H117 H -0.028947 -0.084181 0.656949 0.019 Uiso 1 1 calc R . . . .
C118 C 0.0125(2) -0.1990(4) 0.72359(14) 0.0193(8) Uani 1 1 d . . . . .
H118 H -0.039935 -0.273361 0.721695 0.023 Uiso 1 1 calc R . . . .
C119 C 0.0834(2) -0.2022(4) 0.76535(13) 0.0155(7) Uani 1 1 d . . . . .
H119 H 0.078578 -0.275733 0.793022 0.019 Uiso 1 1 calc R . . . .
C120 C 0.1602(2) -0.0957(4) 0.76523(12) 0.0120(7) Uani 1 1 d . . . . .
H120 H 0.209493 -0.098838 0.793108 0.014 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 O1W 2.213(2) . ?
Cu1 O12 1.981(2) 2_646 ?
Cu1 O13 1.951(2) . ?
Cu1 N4 2.006(3) . ?
Cu1 N5 1.987(3) . ?
Cu2 O11 1.940(2) . ?
Cu2 O13 1.936(2) . ?
Cu2 N1 1.986(3) . ?
Cu2 N2 1.971(2) . ?
Cl1 O1A 1.425(3) . ?
Cl1 O1B 1.438(16) . ?
Cl1 O2A 1.415(3) . ?
Cl1 O2B 1.575(15) . ?
Cl1 O3A 1.434(3) . ?
Cl1 O3B 1.456(14) . ?
Cl1 O4 1.457(2) . ?
Cl2 O5 1.430(3) . ?
Cl2 O6 1.433(3) . ?
Cl2 O7 1.421(3) . ?
Cl2 O8 1.441(2) . ?
O1W H1WA 0.829(19) . ?
O1W H1WB 0.846(19) . ?
O2W H2WA 0.856(19) . ?
O2W H2WB 0.840(19) . ?
O3W H3WA 0.88(2) . ?
O3W H3WB 0.88(2) . ?
O11 C11 1.268(4) . ?
O12 C11 1.258(3) . ?
O13 C12 1.420(3) . ?
N1 C101 1.360(4) . ?
N1 C105 1.347(4) . ?
N2 C106 1.337(4) . ?
N2 C110 1.361(4) . ?
N3 H3 0.841(18) . ?
N3 C105 1.382(4) . ?
N3 C106 1.377(4) . ?
N4 C111 1.358(4) . ?
N4 C115 1.349(4) . ?
N5 C116 1.346(4) . ?
N5 C120 1.349(4) . ?
N6 H6 0.846(19) . ?
N6 C115 1.387(4) . ?
N6 C116 1.376(4) . ?
C11 C12 1.507(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C101 H101 0.9500 . ?
C101 C102 1.369(5) . ?
C102 H102 0.9500 . ?
C102 C103 1.396(4) . ?
C103 H103 0.9500 . ?
C103 C104 1.368(5) . ?
C104 H104 0.9500 . ?
C104 C105 1.399(5) . ?
C106 C107 1.409(4) . ?
C107 H107 0.9500 . ?
C107 C108 1.362(5) . ?
C108 H108 0.9500 . ?
C108 C109 1.401(5) . ?
C109 H109 0.9500 . ?
C109 C110 1.368(4) . ?
C110 H110 0.9500 . ?
C111 H111 0.9500 . ?
C111 C112 1.369(5) . ?
C112 H112 0.9500 . ?
C112 C113 1.405(5) . ?
C113 H113 0.9500 . ?
C113 C114 1.363(5) . ?
C114 H114 0.9500 . ?
C114 C115 1.398(4) . ?
C116 C117 1.409(4) . ?
C117 H117 0.9500 . ?
C117 C118 1.369(5) . ?
C118 H118 0.9500 . ?
C118 C119 1.396(5) . ?
C119 H119 0.9500 . ?
C119 C120 1.375(4) . ?
C120 H120 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O12 Cu1 O1W 106.96(9) 2_646 . ?
O12 Cu1 N4 159.61(10) 2_646 . ?
O12 Cu1 N5 87.80(9) 2_646 . ?
O13 Cu1 O1W 99.44(9) . . ?
O13 Cu1 O12 90.31(9) . 2_646 ?
O13 Cu1 N4 89.07(9) . . ?
O13 Cu1 N5 166.42(9) . . ?
N4 Cu1 O1W 93.23(10) . . ?
N5 Cu1 O1W 93.97(9) . . ?
N5 Cu1 N4 88.04(10) . . ?
O11 Cu2 N1 93.39(10) . . ?
O11 Cu2 N2 171.56(10) . . ?
O13 Cu2 O11 83.66(9) . . ?
O13 Cu2 N1 162.71(10) . . ?
O13 Cu2 N2 93.00(10) . . ?
N2 Cu2 N1 92.05(10) . . ?
O1A Cl1 O3A 110.9(2) . . ?
O1A Cl1 O4 107.11(16) . . ?
O1B Cl1 O2B 103.4(9) . . ?
O1B Cl1 O3B 111.4(9) . . ?
O1B Cl1 O4 115.7(6) . . ?
O2A Cl1 O1A 111.3(2) . . ?
O2A Cl1 O3A 112.1(2) . . ?
O2A Cl1 O4 108.96(17) . . ?
O3A Cl1 O4 106.27(17) . . ?
O3B Cl1 O2B 102.0(9) . . ?
O3B Cl1 O4 115.0(6) . . ?
O4 Cl1 O2B 107.6(6) . . ?
O5 Cl2 O6 109.76(19) . . ?
O5 Cl2 O8 109.36(17) . . ?
O6 Cl2 O8 108.35(17) . . ?
O7 Cl2 O5 108.61(18) . . ?
O7 Cl2 O6 110.81(19) . . ?
O7 Cl2 O8 109.93(17) . . ?
Cu1 O1W H1WA 122(3) . . ?
Cu1 O1W H1WB 131(3) . . ?
H1WA O1W H1WB 106(4) . . ?
H2WA O2W H2WB 95(4) . . ?
H3WA O3W H3WB 104(5) . . ?
C11 O11 Cu2 113.28(19) . . ?
C11 O12 Cu1 130.1(2) . 2_656 ?
Cu2 O13 Cu1 128.96(10) . . ?
C12 O13 Cu1 120.45(18) . . ?
C12 O13 Cu2 110.39(17) . . ?
C101 N1 Cu2 118.4(2) . . ?
C105 N1 Cu2 124.2(2) . . ?
C105 N1 C101 117.4(3) . . ?
C106 N2 Cu2 124.8(2) . . ?
C106 N2 C110 118.3(3) . . ?
C110 N2 Cu2 116.7(2) . . ?
C105 N3 H3 112(3) . . ?
C106 N3 H3 114(3) . . ?
C106 N3 C105 130.5(3) . . ?
C111 N4 Cu1 118.8(2) . . ?
C115 N4 Cu1 121.7(2) . . ?
C115 N4 C111 118.0(3) . . ?
C116 N5 Cu1 122.9(2) . . ?
C116 N5 C120 118.7(3) . . ?
C120 N5 Cu1 117.9(2) . . ?
C115 N6 H6 114(3) . . ?
C116 N6 H6 116(3) . . ?
C116 N6 C115 128.5(3) . . ?
O11 C11 C12 117.4(2) . . ?
O12 C11 O11 124.7(3) . . ?
O12 C11 C12 117.9(3) . . ?
O13 C12 C11 109.5(2) . . ?
O13 C12 H12A 109.8 . . ?
O13 C12 H12B 109.8 . . ?
C11 C12 H12A 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
N1 C101 H101 118.1 . . ?
N1 C101 C102 123.8(3) . . ?
C102 C101 H101 118.1 . . ?
C101 C102 H102 120.9 . . ?
C101 C102 C103 118.1(3) . . ?
C103 C102 H102 120.9 . . ?
C102 C103 H103 120.3 . . ?
C104 C103 C102 119.3(3) . . ?
C104 C103 H103 120.3 . . ?
C103 C104 H104 120.3 . . ?
C103 C104 C105 119.5(3) . . ?
C105 C104 H104 120.3 . . ?
N1 C105 N3 120.6(3) . . ?
N1 C105 C104 121.9(3) . . ?
N3 C105 C104 117.5(3) . . ?
N2 C106 N3 120.8(3) . . ?
N2 C106 C107 121.7(3) . . ?
N3 C106 C107 117.5(3) . . ?
C106 C107 H107 120.4 . . ?
C108 C107 C106 119.1(3) . . ?
C108 C107 H107 120.4 . . ?
C107 C108 H108 120.2 . . ?
C107 C108 C109 119.6(3) . . ?
C109 C108 H108 120.2 . . ?
C108 C109 H109 120.8 . . ?
C110 C109 C108 118.4(3) . . ?
C110 C109 H109 120.8 . . ?
N2 C110 C109 122.9(3) . . ?
N2 C110 H110 118.5 . . ?
C109 C110 H110 118.5 . . ?
N4 C111 H111 118.4 . . ?
N4 C111 C112 123.3(3) . . ?
C112 C111 H111 118.4 . . ?
C111 C112 H112 121.1 . . ?
C111 C112 C113 117.8(3) . . ?
C113 C112 H112 121.1 . . ?
C112 C113 H113 120.1 . . ?
C114 C113 C112 119.8(3) . . ?
C114 C113 H113 120.1 . . ?
C113 C114 H114 120.4 . . ?
C113 C114 C115 119.2(3) . . ?
C115 C114 H114 120.4 . . ?
N4 C115 N6 119.6(3) . . ?
N4 C115 C114 121.7(3) . . ?
N6 C115 C114 118.7(3) . . ?
N5 C116 N6 120.1(3) . . ?
N5 C116 C117 121.0(3) . . ?
N6 C116 C117 118.9(3) . . ?
C116 C117 H117 120.3 . . ?
C118 C117 C116 119.3(3) . . ?
C118 C117 H117 120.3 . . ?
C117 C118 H118 120.2 . . ?
C117 C118 C119 119.6(3) . . ?
C119 C118 H118 120.2 . . ?
C118 C119 H119 121.0 . . ?
C120 C119 C118 118.0(3) . . ?
C120 C119 H119 121.0 . . ?
N5 C120 C119 123.3(3) . . ?
N5 C120 H120 118.4 . . ?
C119 C120 H120 118.4 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
