# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_Compound1
_database_code_depnum_ccdc_archive 'CCDC 1940509'
loop_
_audit_author_name
_audit_author_address
'Antonio Rodriquez-Dieguez'
;University of Granada
Spain
;
_audit_update_record             
;
2020-01-28 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 Co N4 O6'
_chemical_formula_weight         417.24

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   5.3010(2)
_cell_length_b                   10.0099(3)
_cell_length_c                   15.2097(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.8820(10)
_cell_angle_gamma                90
_cell_volume                     801.25(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10249
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      28.70

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_F_000             426
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    1.117
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.645
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0706 before and 0.0469 after correction.
The Ratio of minimum to maximum transmission is 0.9433.
The λ/2 correction factor is 0.00150.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15855
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.441
_diffrn_reflns_theta_max         28.714
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2068
_reflns_number_gt                1890
_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 ApexII'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0369P)²+0.6023P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2068
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0246
_refine_ls_wR_factor_ref         0.0662
_refine_ls_wR_factor_gt          0.0642
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_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
Co1 Co 0.0000 0.0000 0.0000 0.00617(8) Uani 1 2 d S . P . .
C1 C 0.0910(2) 0.22778(12) 0.14154(8) 0.0092(2) Uani 1 1 d . . . . .
H1 H -0.0398 0.1956 0.1713 0.011 Uiso 1 1 calc R U . . .
C2 C 0.2472(2) 0.33877(12) 0.16906(8) 0.0080(2) Uani 1 1 d . . . . .
C3 C 0.2733(2) 0.42638(12) 0.24291(8) 0.0083(2) Uani 1 1 d . . . . .
C4 C 0.4497(3) 0.52813(13) 0.24322(9) 0.0114(2) Uani 1 1 d . . . . .
H4 H 0.4650 0.5892 0.2896 0.014 Uiso 1 1 calc R U . . .
C5 C 0.6080(3) 0.54218(14) 0.17502(9) 0.0130(2) Uani 1 1 d . . . . .
H5 H 0.7220 0.6130 0.1773 0.016 Uiso 1 1 calc R U . . .
C6 C 0.5969(3) 0.45336(14) 0.10551(9) 0.0120(2) Uani 1 1 d . . . . .
H6 H 0.7055 0.4602 0.0620 0.014 Uiso 1 1 calc R U . . .
C7 C 0.4128(2) 0.35157(13) 0.10359(8) 0.0094(2) Uani 1 1 d . . . . .
C8 C -0.1235(2) -0.09612(12) 0.18067(8) 0.0083(2) Uani 1 1 d . . . . .
N1 N 0.1582(2) 0.17600(11) 0.06697(7) 0.0097(2) Uani 1 1 d . . . . .
N2 N 0.3522(2) 0.25249(11) 0.04333(7) 0.0113(2) Uani 1 1 d . . . . .
H2 H 0.4263 0.2399 -0.0033 0.014 Uiso 1 1 calc R U . . .
O1 O -0.19964(17) -0.03298(10) 0.10855(6) 0.00952(18) Uani 1 1 d . . . . .
O2 O 0.05877(19) -0.17573(10) 0.19016(6) 0.0149(2) Uani 1 1 d . . . . .
O1W O 0.31161(17) -0.11486(9) 0.06002(6) 0.00976(18) Uani 1 1 d . . . . .
H2W1 H 0.4450 -0.0691 0.0803 0.012 Uiso 1 1 d R U . . .
H1W1 H 0.2435 -0.1508 0.1061 0.012 Uiso 1 1 d 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
Co1 O1 2.0913(9) . ?
Co1 O1 2.0913(9) 3 ?
Co1 O1W 2.1266(9) . ?
Co1 O1W 2.1266(9) 3 ?
Co1 N1 2.1540(11) . ?
Co1 N1 2.1541(11) 3 ?
C1 N1 1.3337(15) . ?
C1 C2 1.4184(17) . ?
C1 H1 0.9300 . ?
C2 C7 1.4101(16) . ?
C2 C3 1.4186(16) . ?
C3 C4 1.3821(17) . ?
C3 C8 1.5012(16) 2 ?
C4 C5 1.4172(18) . ?
C4 H4 0.9300 . ?
C5 C6 1.3771(18) . ?
C5 H5 0.9300 . ?
C6 C7 1.4087(18) . ?
C6 H6 0.9300 . ?
C7 N2 1.3624(16) . ?
C8 O2 1.2475(16) . ?
C8 O1 1.2881(15) . ?
C8 C3 1.5013(16) 2_545 ?
N1 N2 1.3645(15) . ?
N2 H2 0.8600 . ?
O1W H2W1 0.8671 . ?
O1W H1W1 0.9002 . ?

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 Co1 O1 180.0 . 3 ?
O1 Co1 O1W 90.93(3) . . ?
O1 Co1 O1W 89.07(3) 3 . ?
O1 Co1 O1W 89.06(3) . 3 ?
O1 Co1 O1W 90.94(3) 3 3 ?
O1W Co1 O1W 180.0 . 3 ?
O1 Co1 N1 87.76(4) . . ?
O1 Co1 N1 92.24(4) 3 . ?
O1W Co1 N1 90.05(4) . . ?
O1W Co1 N1 89.95(4) 3 . ?
O1 Co1 N1 92.24(4) . 3 ?
O1 Co1 N1 87.76(4) 3 3 ?
O1W Co1 N1 89.95(4) . 3 ?
O1W Co1 N1 90.05(4) 3 3 ?
N1 Co1 N1 180.0 . 3 ?
N1 C1 C2 110.45(11) . . ?
N1 C1 H1 124.8 . . ?
C2 C1 H1 124.8 . . ?
C7 C2 C3 119.53(11) . . ?
C7 C2 C1 104.69(11) . . ?
C3 C2 C1 135.73(11) . . ?
C4 C3 C2 117.39(11) . . ?
C4 C3 C8 121.89(11) . 2 ?
C2 C3 C8 120.65(11) . 2 ?
C3 C4 C5 122.02(12) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C6 C5 C4 121.55(12) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 116.66(11) . . ?
C5 C6 H6 121.7 . . ?
C7 C6 H6 121.7 . . ?
N2 C7 C6 130.34(12) . . ?
N2 C7 C2 107.00(11) . . ?
C6 C7 C2 122.64(11) . . ?
O2 C8 O1 124.83(11) . . ?
O2 C8 C3 118.72(11) . 2_545 ?
O1 C8 C3 116.42(11) . 2_545 ?
C1 N1 N2 107.01(10) . . ?
C1 N1 Co1 126.26(9) . . ?
N2 N1 Co1 126.69(8) . . ?
C7 N2 N1 110.83(10) . . ?
C7 N2 H2 124.6 . . ?
N1 N2 H2 124.6 . . ?
C8 O1 Co1 127.82(8) . . ?
Co1 O1W H2W1 115.2 . . ?
Co1 O1W H1W1 100.7 . . ?
H2W1 O1W H1W1 108.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1W 0.86 2.13 2.8663(14) 143.6 3_655
O1W H2W1 O1 0.87 1.92 2.7333(13) 156.5 1_655
O1W H1W1 O2 0.90 1.72 2.5926(13) 162.5 .

_refine_diff_density_max         0.421
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.075

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_Compound5
_database_code_depnum_ccdc_archive 'CCDC 1940512'
loop_
_audit_author_name
_audit_author_address
'Antonio Rodriquez-Dieguez'
;University of Granada
Spain
;
_audit_update_record             
;
2020-01-28 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H10 Cd N4 O4'
_chemical_formula_weight         434.68

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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

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

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

_cell_length_a                   12.3609(15)
_cell_length_b                   9.9856(11)
_cell_length_c                   12.3887(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1529.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    17935
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      28.9

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.888
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    1.459
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.621
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0706 before and 0.0469 after correction.
The Ratio of minimum to maximum transmission is 0.9433.
The λ/2 correction factor is 0.00150.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29005
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.622
_diffrn_reflns_theta_max         28.942
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2010
_reflns_number_gt                1829
_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 ApexII'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+96.3397P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2010
_refine_ls_number_parameters     114
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1192
_refine_ls_R_factor_gt           0.1130
_refine_ls_wR_factor_ref         0.2917
_refine_ls_wR_factor_gt          0.2890
_refine_ls_goodness_of_fit_ref   1.496
_refine_ls_restrained_S_all      1.482
_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
Cd1 Cd 0.7500 0.7500 0.26133(10) 0.0140(4) Uani 1 2 d S T P . .
O1 O 0.5882(7) 0.6573(9) 0.2108(7) 0.0143(18) Uani 1 1 d . . . . .
O2 O 0.6390(7) 0.8292(9) 0.1107(8) 0.0128(18) Uani 1 1 d . . . . .
N1 N 0.3088(8) 0.4217(10) 0.1343(8) 0.0091(19) Uani 1 1 d . U . . .
N2 N 0.2760(8) 0.4547(11) 0.0334(8) 0.0102(19) Uani 1 1 d . U . . .
H2 H 0.2247 0.4154 -0.0012 0.012 Uiso 1 1 calc R U . . .
C1 C 0.3911(10) 0.5030(12) 0.1602(11) 0.012(2) Uani 1 1 d . . . . .
H1 H 0.4291 0.5005 0.2250 0.015 Uiso 1 1 calc R U . . .
C2 C 0.4118(9) 0.5940(12) 0.0736(10) 0.010(2) Uani 1 1 d . . . . .
C3 C 0.4868(10) 0.6979(13) 0.0516(10) 0.012(2) Uani 1 1 d . U . . .
C4 C 0.4799(10) 0.7634(15) -0.0465(10) 0.016(2) Uani 1 1 d . U . . .
H4 H 0.5248 0.8362 -0.0603 0.019 Uiso 1 1 calc R U . . .
C5 C 0.4054(11) 0.7211(12) -0.1261(12) 0.017(3) Uani 1 1 d . . . . .
H5 H 0.4058 0.7635 -0.1929 0.021 Uiso 1 1 calc R U . . .
C6 C 0.3319(10) 0.6192(13) -0.1082(12) 0.017(3) Uani 1 1 d . . . . .
H6 H 0.2828 0.5922 -0.1608 0.021 Uiso 1 1 calc R U . . .
C7 C 0.3358(9) 0.5589(12) -0.0061(9) 0.005(2) Uani 1 1 d . U . . .
C8 C 0.5753(9) 0.7296(12) 0.1292(9) 0.009(2) Uani 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 N1 2.267(10) 4_655 ?
Cd1 N1 2.267(10) 3_565 ?
Cd1 O1 2.291(9) . ?
Cd1 O1 2.291(9) 2_665 ?
Cd1 O2 2.448(10) 2_665 ?
Cd1 O2 2.448(9) . ?
Cd1 C8 2.717(12) 2_665 ?
Cd1 C8 2.717(12) . ?
O1 C8 1.252(15) . ?
O2 C8 1.289(14) . ?
N1 C1 1.340(15) . ?
N1 N2 1.356(14) . ?
N1 Cd1 2.267(10) 3_465 ?
N2 C7 1.367(15) . ?
N2 H2 0.8600 . ?
C1 C2 1.430(17) . ?
C1 H1 0.9300 . ?
C2 C7 1.407(15) . ?
C2 C3 1.417(17) . ?
C3 C4 1.383(18) . ?
C3 C8 1.491(16) . ?
C4 C5 1.414(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(17) . ?
C5 H5 0.9300 . ?
C6 C7 1.402(17) . ?
C6 H6 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
N1 Cd1 N1 110.5(5) 4_655 3_565 ?
N1 Cd1 O1 100.5(3) 4_655 . ?
N1 Cd1 O1 97.5(3) 3_565 . ?
N1 Cd1 O1 97.5(3) 4_655 2_665 ?
N1 Cd1 O1 100.5(3) 3_565 2_665 ?
O1 Cd1 O1 148.3(5) . 2_665 ?
N1 Cd1 O2 149.2(3) 4_655 2_665 ?
N1 Cd1 O2 90.6(3) 3_565 2_665 ?
O1 Cd1 O2 98.7(3) . 2_665 ?
O1 Cd1 O2 55.4(3) 2_665 2_665 ?
N1 Cd1 O2 90.6(3) 4_655 . ?
N1 Cd1 O2 149.2(3) 3_565 . ?
O1 Cd1 O2 55.4(3) . . ?
O1 Cd1 O2 98.7(3) 2_665 . ?
O2 Cd1 O2 80.7(4) 2_665 . ?
N1 Cd1 C8 122.8(4) 4_655 2_665 ?
N1 Cd1 C8 98.3(4) 3_565 2_665 ?
O1 Cd1 C8 124.0(3) . 2_665 ?
O1 Cd1 C8 27.3(3) 2_665 2_665 ?
O2 Cd1 C8 28.3(3) 2_665 2_665 ?
O2 Cd1 C8 87.8(3) . 2_665 ?
N1 Cd1 C8 98.3(4) 4_655 . ?
N1 Cd1 C8 122.8(4) 3_565 . ?
O1 Cd1 C8 27.3(3) . . ?
O1 Cd1 C8 124.0(3) 2_665 . ?
O2 Cd1 C8 87.8(3) 2_665 . ?
O2 Cd1 C8 28.3(3) . . ?
C8 Cd1 C8 106.0(5) 2_665 . ?
C8 O1 Cd1 95.7(7) . . ?
C8 O2 Cd1 87.6(7) . . ?
C1 N1 N2 107.5(10) . . ?
C1 N1 Cd1 124.4(8) . 3_465 ?
N2 N1 Cd1 127.9(8) . 3_465 ?
N1 N2 C7 110.7(10) . . ?
N1 N2 H2 124.7 . . ?
C7 N2 H2 124.7 . . ?
N1 C1 C2 109.9(11) . . ?
N1 C1 H1 125.0 . . ?
C2 C1 H1 125.0 . . ?
C7 C2 C3 119.0(11) . . ?
C7 C2 C1 104.4(10) . . ?
C3 C2 C1 136.6(11) . . ?
C4 C3 C2 118.4(12) . . ?
C4 C3 C8 120.8(12) . . ?
C2 C3 C8 120.7(11) . . ?
C3 C4 C5 120.8(13) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 122.5(13) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C5 C6 C7 116.0(13) . . ?
C5 C6 H6 122.0 . . ?
C7 C6 H6 122.0 . . ?
N2 C7 C6 129.1(11) . . ?
N2 C7 C2 107.5(10) . . ?
C6 C7 C2 123.3(11) . . ?
O1 C8 O2 120.7(11) . . ?
O1 C8 C3 119.5(11) . . ?
O2 C8 C3 119.8(11) . . ?
O1 C8 Cd1 57.0(6) . . ?
O2 C8 Cd1 64.2(6) . . ?
C3 C8 Cd1 171.0(9) . . ?

_refine_diff_density_max         1.640
_refine_diff_density_min         -2.878
_refine_diff_density_rms         0.329

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_Compound2
_database_code_depnum_ccdc_archive 'CCDC 1940511'
loop_
_audit_author_name
_audit_author_address
'Antonio Rodriquez-Dieguez'
;University of Granada
Spain
;
_audit_update_record             
;
2020-01-28 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 N4 Ni O6'
_chemical_formula_weight         417.02

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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   5.3050(3)
_cell_length_b                   9.9880(4)
_cell_length_c                   15.0820(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.362(2)
_cell_angle_gamma                90
_cell_volume                     792.55(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    12778
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      58.71

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            'pale green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    1.271
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.689
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0706 before and 0.0469 after correction.
The Ratio of minimum to maximum transmission is 0.9433.
The λ/2 correction factor is 0.00150.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20899
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.723
_diffrn_reflns_theta_max         28.744
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2056
_reflns_number_gt                1869
_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 ApexII'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0274P)²+0.5518P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2056
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0223
_refine_ls_wR_factor_ref         0.0571
_refine_ls_wR_factor_gt          0.0558
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
Ni1 Ni 0.0000 0.5000 0.5000 0.00588(7) Uani 1 2 d S . P . .
C1 C 0.0863(2) 0.27576(12) 0.64201(8) 0.0092(2) Uani 1 1 d . . . . .
H1 H -0.0443 0.3074 0.6720 0.011 Uiso 1 1 calc R U . . .
C2 C 0.2435(2) 0.16451(12) 0.66951(8) 0.0083(2) Uani 1 1 d . . . . .
C3 C 0.2705(2) 0.07603(12) 0.74346(8) 0.0084(2) Uani 1 1 d . . . . .
C4 C 0.4469(2) -0.02603(13) 0.74346(9) 0.0115(2) Uani 1 1 d . . . . .
H4 H 0.4627 -0.0880 0.7899 0.014 Uiso 1 1 calc R U . . .
C5 C 0.6043(3) -0.03878(13) 0.67478(9) 0.0134(3) Uani 1 1 d . . . . .
H5 H 0.7185 -0.1097 0.6768 0.016 Uiso 1 1 calc R U . . .
C6 C 0.5926(3) 0.05113(14) 0.60522(9) 0.0124(2) Uani 1 1 d . . . . .
H6 H 0.7009 0.0451 0.5615 0.015 Uiso 1 1 calc R U . . .
C7 C 0.4080(2) 0.15262(13) 0.60365(8) 0.0097(2) Uani 1 1 d . . . . .
C8 C 0.1220(2) 0.40241(12) 0.32071(8) 0.0084(2) Uani 1 1 d . . . . .
N1 N 0.1520(2) 0.32854(10) 0.56718(7) 0.0093(2) Uani 1 1 d . . . . .
N2 N 0.3464(2) 0.25265(11) 0.54321(7) 0.0112(2) Uani 1 1 d . . . . .
H2 H 0.4199 0.2661 0.4964 0.013 Uiso 1 1 calc R U . . .
O1 O 0.19874(17) 0.46708(9) 0.39284(6) 0.00908(17) Uani 1 1 d . . . . .
O2 O -0.05982(18) 0.32228(10) 0.31133(6) 0.0151(2) Uani 1 1 d . . . . .
O1W O -0.30927(16) 0.38592(9) 0.44161(6) 0.00951(17) Uani 1 1 d . . . . .
H2W1 H -0.4399 0.4322 0.4207 0.011 Uiso 1 1 d R U . . .
H1W1 H -0.2444 0.3503 0.3962 0.011 Uiso 1 1 d 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
Ni1 O1 2.0660(9) 3_566 ?
Ni1 O1 2.0660(9) . ?
Ni1 O1W 2.0965(9) . ?
Ni1 O1W 2.0966(9) 3_566 ?
Ni1 N1 2.0977(10) 3_566 ?
Ni1 N1 2.0977(10) . ?
C1 N1 1.3318(16) . ?
C1 C2 1.4189(16) . ?
C1 H1 0.9300 . ?
C2 C7 1.4090(16) . ?
C2 C3 1.4158(16) . ?
C3 C4 1.3841(17) . ?
C3 C8 1.5030(16) 4_566 ?
C4 C5 1.4170(18) . ?
C4 H4 0.9300 . ?
C5 C6 1.3763(18) . ?
C5 H5 0.9300 . ?
C6 C7 1.4073(18) . ?
C6 H6 0.9300 . ?
C7 N2 1.3637(16) . ?
C8 O2 1.2475(15) . ?
C8 O1 1.2856(15) . ?
C8 C3 1.5030(16) 4_565 ?
N1 N2 1.3653(14) . ?
N2 H2 0.8600 . ?
O1W H2W1 0.8589 . ?
O1W H1W1 0.8798 . ?

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 Ni1 O1 180.0 3_566 . ?
O1 Ni1 O1W 87.98(3) 3_566 . ?
O1 Ni1 O1W 92.02(3) . . ?
O1 Ni1 O1W 92.02(3) 3_566 3_566 ?
O1 Ni1 O1W 87.98(3) . 3_566 ?
O1W Ni1 O1W 180.0 . 3_566 ?
O1 Ni1 N1 92.57(4) 3_566 3_566 ?
O1 Ni1 N1 87.43(4) . 3_566 ?
O1W Ni1 N1 90.52(4) . 3_566 ?
O1W Ni1 N1 89.48(4) 3_566 3_566 ?
O1 Ni1 N1 87.43(4) 3_566 . ?
O1 Ni1 N1 92.57(4) . . ?
O1W Ni1 N1 89.48(4) . . ?
O1W Ni1 N1 90.52(4) 3_566 . ?
N1 Ni1 N1 180.00(3) 3_566 . ?
N1 C1 C2 110.48(11) . . ?
N1 C1 H1 124.8 . . ?
C2 C1 H1 124.8 . . ?
C7 C2 C3 119.57(11) . . ?
C7 C2 C1 104.71(11) . . ?
C3 C2 C1 135.68(11) . . ?
C4 C3 C2 117.38(11) . . ?
C4 C3 C8 121.81(11) . 4_566 ?
C2 C3 C8 120.73(11) . 4_566 ?
C3 C4 C5 121.87(12) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 121.69(12) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 116.51(12) . . ?
C5 C6 H6 121.7 . . ?
C7 C6 H6 121.7 . . ?
N2 C7 C6 130.21(11) . . ?
N2 C7 C2 107.00(11) . . ?
C6 C7 C2 122.78(11) . . ?
O2 C8 O1 125.08(11) . . ?
O2 C8 C3 118.58(11) . 4_565 ?
O1 C8 C3 116.32(11) . 4_565 ?
C1 N1 N2 107.05(10) . . ?
C1 N1 Ni1 127.32(9) . . ?
N2 N1 Ni1 125.59(8) . . ?
C7 N2 N1 110.75(10) . . ?
C7 N2 H2 124.6 . . ?
N1 N2 H2 124.6 . . ?
C8 O1 Ni1 127.15(8) . . ?
Ni1 O1W H2W1 114.4 . . ?
Ni1 O1W H1W1 100.6 . . ?
H2W1 O1W H1W1 108.0 . . ?

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 H2 O1W 0.86 2.12 2.8591(14) 144.1 1_655
O1W H2W1 O1 0.86 1.94 2.7419(13) 154.7 1_455
O1W H1W1 O2 0.88 1.73 2.5850(13) 162.8 .

_refine_diff_density_max         0.394
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.064

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_Compound3
_database_code_depnum_ccdc_archive 'CCDC 1940510'
loop_
_audit_author_name
_audit_author_address
'Antonio Rodriquez-Dieguez'
;University of Granada
Spain
;
_audit_update_record             
;
2020-01-28 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 Cu N4 O5'
_chemical_formula_weight         403.84

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   10.1061(8)
_cell_length_b                   9.8617(7)
_cell_length_c                   14.7053(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.716(2)
_cell_angle_gamma                90
_cell_volume                     1460.62(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5089
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      28.5

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.836
_exptl_crystal_F_000             820
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.537
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.665
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0706 before and 0.0469 after correction.
The Ratio of minimum to maximum transmission is 0.9433.
The λ/2 correction factor is 0.00150.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31300
_diffrn_reflns_av_unetI/netI     0.0784
_diffrn_reflns_av_R_equivalents  0.1496
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.489
_diffrn_reflns_theta_max         28.767
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3769
_reflns_number_gt                2769
_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 ApexII'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0147P)²+9.7659P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3769
_refine_ls_number_parameters     225
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1269
_refine_ls_R_factor_gt           0.0868
_refine_ls_wR_factor_ref         0.1355
_refine_ls_wR_factor_gt          0.1254
_refine_ls_goodness_of_fit_ref   1.201
_refine_ls_restrained_S_all      1.206
_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 0.77554(6) 0.00458(7) 0.03593(4) 0.00606(14) Uani 1 1 d . . . . .
C1A C 0.7276(5) -0.2085(5) 0.1790(3) 0.0093(10) Uani 1 1 d . . . . .
H1A H 0.7962 -0.1784 0.2200 0.011 Uiso 1 1 calc R U . . .
C2A C 0.6424(5) -0.3184(5) 0.1945(3) 0.0097(10) Uani 1 1 d . . . . .
C3A C 0.6283(5) -0.4109(5) 0.2664(3) 0.0082(10) Uani 1 1 d . . . . .
C4A C 0.5331(5) -0.5118(6) 0.2513(3) 0.0155(11) Uani 1 1 d . . . . .
H4A H 0.5245 -0.5769 0.2962 0.019 Uiso 1 1 calc R U . . .
C5A C 0.4490(5) -0.5185(6) 0.1699(3) 0.0182(12) Uani 1 1 d . . . . .
H5A H 0.3866 -0.5877 0.1626 0.022 Uiso 1 1 calc R U . . .
C6A C 0.4571(5) -0.4257(5) 0.1012(3) 0.0149(11) Uani 1 1 d . . . . .
H6A H 0.3999 -0.4284 0.0484 0.018 Uiso 1 1 calc R U . . .
C7A C 0.5567(5) -0.3261(5) 0.1148(3) 0.0098(10) Uani 1 1 d . . . . .
C8A C 0.7124(5) -0.1022(5) -0.1434(3) 0.0116(10) Uani 1 1 d . . . . .
N1A N 0.6959(4) -0.1545(4) 0.0978(3) 0.0085(8) Uani 1 1 d . . . . .
N2A N 0.5928(4) -0.2275(4) 0.0584(3) 0.0116(9) Uani 1 1 d . . . . .
H2A H 0.5554 -0.2128 0.0046 0.014 Uiso 1 1 calc R U . . .
O1A O 0.6697(3) -0.0354(3) -0.0775(2) 0.0114(8) Uiso 1 1 d . . . . .
O2A O 0.8103(4) -0.1755(4) -0.1403(3) 0.0191(9) Uani 1 1 d . . . . .
C1B C 0.8436(5) 0.2000(5) -0.1095(3) 0.0089(10) Uani 1 1 d . U . . .
H1B H 0.7722 0.1733 -0.1495 0.011 Uiso 1 1 calc R U . . .
C2B C 0.9328(5) 0.3050(5) -0.1275(3) 0.0078(9) Uani 1 1 d . . . . .
C3B C 0.9510(5) 0.3963(5) -0.1995(3) 0.0084(10) Uani 1 1 d . . . . .
C4B C 1.0502(5) 0.4895(6) -0.1868(3) 0.0112(10) Uani 1 1 d . . . . .
H4B H 1.0626 0.5509 -0.2333 0.013 Uiso 1 1 calc R U . . .
C5B C 1.1357(4) 0.4968(6) -0.1050(3) 0.0133(9) Uani 1 1 d . . . . .
H5B H 1.2005 0.5639 -0.0989 0.016 Uiso 1 1 calc R U . . .
C6B C 1.1241(5) 0.4063(5) -0.0349(3) 0.0090(10) Uani 1 1 d . . . . .
H6B H 1.1808 0.4087 0.0182 0.011 Uiso 1 1 calc R U . . .
C7B C 1.0210(5) 0.3094(5) -0.0481(3) 0.0071(9) Uani 1 1 d . . . . .
C8B C 0.8645(5) 0.1152(5) 0.2121(3) 0.0118(11) Uani 1 1 d . . . . .
N1B N 0.8741(4) 0.1447(4) -0.0291(3) 0.0083(8) Uani 1 1 d . . . . .
N2B N 0.9823(4) 0.2115(4) 0.0093(3) 0.0077(8) Uiso 1 1 d . . . . .
H2B H 1.0208 0.1944 0.0624 0.009 Uiso 1 1 calc R U . . .
O1B O 0.8907(4) 0.0334(3) 0.1492(2) 0.0106(8) Uani 1 1 d . . . . .
O2B O 0.7759(4) 0.2029(4) 0.2065(3) 0.0191(9) Uani 1 1 d . U . . .
O1W O 0.5985(4) 0.1422(4) 0.0765(2) 0.0159(8) Uani 1 1 d . . . . .
H1W1 H 0.6397 0.1938 0.1172 0.019 Uiso 1 1 d R U . . .
H2W1 H 0.5404 0.0898 0.0963 0.019 Uiso 1 1 d R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1A 1.947(3) . ?
Cu1 O1B 1.972(3) . ?
Cu1 N1B 1.993(4) . ?
Cu1 N1A 2.014(4) . ?
Cu1 O1W 2.362(4) . ?
C1A N1A 1.322(6) . ?
C1A C2A 1.415(7) . ?
C1A H1A 0.9300 . ?
C2A C7A 1.401(7) . ?
C2A C3A 1.413(7) . ?
C3A C4A 1.389(7) . ?
C3A C8A 1.521(7) 4_556 ?
C4A C5A 1.412(7) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.370(7) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.409(7) . ?
C6A H6A 0.9300 . ?
C7A N2A 1.348(6) . ?
C8A O2A 1.224(6) . ?
C8A O1A 1.275(6) . ?
C8A C3A 1.521(7) 4 ?
N1A N2A 1.356(6) . ?
N2A H2A 0.8600 . ?
C1B N1B 1.317(6) . ?
C1B C2B 1.412(7) . ?
C1B H1B 0.9300 . ?
C2B C7B 1.410(6) . ?
C2B C3B 1.413(7) . ?
C3B C4B 1.362(7) . ?
C3B C8B 1.510(7) 4_565 ?
C4B C5B 1.423(7) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.376(7) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.415(7) . ?
C6B H6B 0.9300 . ?
C7B N2B 1.361(6) . ?
C8B O2B 1.243(6) . ?
C8B O1B 1.271(6) . ?
C8B C3B 1.510(7) 4_566 ?
N1B N2B 1.359(6) . ?
N2B H2B 0.8600 . ?
O1W H1W1 0.8658 . ?
O1W H2W1 0.8517 . ?

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
O1A Cu1 O1B 175.82(15) . . ?
O1A Cu1 N1B 89.45(16) . . ?
O1B Cu1 N1B 91.26(15) . . ?
O1A Cu1 N1A 90.98(15) . . ?
O1B Cu1 N1A 87.75(15) . . ?
N1B Cu1 N1A 172.18(18) . . ?
O1A Cu1 O1W 87.63(13) . . ?
O1B Cu1 O1W 96.35(14) . . ?
N1B Cu1 O1W 98.14(15) . . ?
N1A Cu1 O1W 89.68(15) . . ?
N1A C1A C2A 110.4(4) . . ?
N1A C1A H1A 124.8 . . ?
C2A C1A H1A 124.8 . . ?
C7A C2A C3A 119.8(5) . . ?
C7A C2A C1A 104.4(4) . . ?
C3A C2A C1A 135.8(5) . . ?
C4A C3A C2A 117.0(4) . . ?
C4A C3A C8A 122.0(4) . 4_556 ?
C2A C3A C8A 120.9(4) . 4_556 ?
C3A C4A C5A 122.0(5) . . ?
C3A C4A H4A 119.0 . . ?
C5A C4A H4A 119.0 . . ?
C6A C5A C4A 121.7(5) . . ?
C6A C5A H5A 119.1 . . ?
C4A C5A H5A 119.1 . . ?
C5A C6A C7A 116.5(5) . . ?
C5A C6A H6A 121.8 . . ?
C7A C6A H6A 121.8 . . ?
N2A C7A C2A 107.2(4) . . ?
N2A C7A C6A 129.9(5) . . ?
C2A C7A C6A 122.8(5) . . ?
O2A C8A O1A 126.9(5) . . ?
O2A C8A C3A 118.4(5) . 4 ?
O1A C8A C3A 114.7(4) . 4 ?
C1A N1A N2A 107.0(4) . . ?
C1A N1A Cu1 130.1(3) . . ?
N2A N1A Cu1 122.8(3) . . ?
C7A N2A N1A 111.0(4) . . ?
C7A N2A H2A 124.5 . . ?
N1A N2A H2A 124.5 . . ?
C8A O1A Cu1 124.0(3) . . ?
N1B C1B C2B 111.5(4) . . ?
N1B C1B H1B 124.3 . . ?
C2B C1B H1B 124.3 . . ?
C7B C2B C1B 103.8(4) . . ?
C7B C2B C3B 119.3(4) . . ?
C1B C2B C3B 137.0(5) . . ?
C4B C3B C2B 117.8(4) . . ?
C4B C3B C8B 122.4(4) . 4_565 ?
C2B C3B C8B 119.7(4) . 4_565 ?
C3B C4B C5B 122.6(5) . . ?
C3B C4B H4B 118.7 . . ?
C5B C4B H4B 118.7 . . ?
C6B C5B C4B 121.1(5) . . ?
C6B C5B H5B 119.4 . . ?
C4B C5B H5B 119.4 . . ?
C5B C6B C7B 116.2(4) . . ?
C5B C6B H6B 121.9 . . ?
C7B C6B H6B 121.9 . . ?
N2B C7B C2B 107.3(4) . . ?
N2B C7B C6B 129.8(4) . . ?
C2B C7B C6B 122.8(4) . . ?
O2B C8B O1B 125.8(5) . . ?
O2B C8B C3B 118.1(4) . 4_566 ?
O1B C8B C3B 116.0(5) . 4_566 ?
C1B N1B N2B 107.0(4) . . ?
C1B N1B Cu1 129.0(3) . . ?
N2B N1B Cu1 123.6(3) . . ?
N1B N2B C7B 110.5(4) . . ?
N1B N2B H2B 124.8 . . ?
C7B N2B H2B 124.8 . . ?
C8B O1B Cu1 124.2(3) . . ?
Cu1 O1W H1W1 100.4 . . ?
Cu1 O1W H2W1 107.2 . . ?
H1W1 O1W H2W1 115.2 . . ?

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
N2A H2A O1W 0.86 2.01 2.784(5) 150.0 3_655
N2B H2B O2A 0.86 1.98 2.750(6) 147.8 3_755
O1W H1W1 O2B 0.87 1.82 2.582(5) 144.9 .
O1W H2W1 O1A 0.85 2.19 2.909(5) 142.7 3_655

_refine_diff_density_max         0.663
_refine_diff_density_min         -1.303
_refine_diff_density_rms         0.147

_shelxl_version_number           2014-3



