# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_rm318
_database_code_depnum_ccdc_archive 'CCDC 1919278'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;University of Montreal
Canada
;
_audit_update_record             
;
2019-05-28 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;
_audit_creation_date             2019-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 Co N12 O2, 2(C2 H6 O S), 2(N O3)'
_chemical_formula_sum            'C20 H30 Co N14 O10 S2'
_chemical_formula_weight         749.63
_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 0.0137 0.0057 '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'
Co Co -0.6627 2.9049 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   24.2963(6)
_cell_length_b                   10.0731(3)
_cell_length_c                   13.8796(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.106(1)
_cell_angle_gamma                90
_cell_volume                     3169.00(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9877
_cell_measurement_temperature    150
_cell_measurement_theta_max      60.698
_cell_measurement_theta_min      3.394
_shelx_estimated_absorpt_T_max   0.786
_shelx_estimated_absorpt_T_min   0.632
_exptl_absorpt_coefficient_mu    4.207
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1346 before and 0.0660 after correction. The Ratio of minimum to maximum transmission is 0.8905. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1548
_exptl_crystal_recrystallization_method 'Crystallized from DMSO/EtOAc'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24490
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.742
_diffrn_reflns_theta_min         3.393
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3113
_reflns_number_total             3634
_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 (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.00036(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3634
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.026
_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)+(0.0566P)²+6.8502P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1122
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Rotating group:
 O1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4)
2.c X=CH2 refined with riding coordinates:
 N5(H5A,H5B), N6(H6A,H6B)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
Co1 Co 0.500000 0.61294(4) 0.250000 0.01576(14) Uani 1 2 d S T P . .
O1 O 0.58749(7) 0.63514(17) 0.35751(12) 0.0227(4) Uani 1 1 d . . . . .
H1A H 0.605801 0.698626 0.337972 0.034 Uiso 1 1 d GR . . . .
H1B H 0.607741 0.561717 0.362694 0.034 Uiso 1 1 d GR . . . .
C1 C 0.48076(10) 0.3259(2) 0.28092(17) 0.0189(5) Uani 1 1 d . . . . .
N1 N 0.47203(8) 0.44814(18) 0.31096(14) 0.0175(4) Uani 1 1 d . . . . .
C2 C 0.45455(11) 0.2160(2) 0.30736(18) 0.0228(5) Uani 1 1 d . . . . .
H2 H 0.460144 0.129607 0.285066 0.027 Uiso 1 1 calc R . . . .
N2 N 0.46893(8) 0.69393(18) 0.36637(14) 0.0181(4) Uani 1 1 d . . . . .
C3 C 0.42006(11) 0.2353(2) 0.36700(19) 0.0252(5) Uani 1 1 d . . . . .
H3 H 0.401556 0.161585 0.385446 0.030 Uiso 1 1 calc R . . . .
N3 N 0.44427(9) 0.85730(19) 0.46941(15) 0.0205(4) Uani 1 1 d . . . . .
N4 N 0.40868(9) 0.63381(19) 0.46205(15) 0.0201(4) Uani 1 1 d . . . . .
C4 C 0.41246(11) 0.3618(2) 0.39985(18) 0.0232(5) Uani 1 1 d . . . . .
H4 H 0.389539 0.376017 0.441773 0.028 Uiso 1 1 calc R . . . .
C5 C 0.43940(10) 0.4668(2) 0.36948(16) 0.0185(5) Uani 1 1 d . . . . .
N5 N 0.50886(9) 0.90432(19) 0.38792(16) 0.0238(4) Uani 1 1 d . . . . .
H5A H 0.512983 0.984605 0.414584 0.029 Uiso 1 1 calc R . . . .
H5B H 0.528387 0.881441 0.347997 0.029 Uiso 1 1 calc R . . . .
N6 N 0.38150(9) 0.7944(2) 0.55246(16) 0.0246(4) Uani 1 1 d . . . . .
H6A H 0.382804 0.875700 0.576335 0.030 Uiso 1 1 calc R . . . .
H6B H 0.360122 0.733501 0.568121 0.030 Uiso 1 1 calc R . . . .
C6 C 0.43754(10) 0.6077(2) 0.40060(17) 0.0181(4) Uani 1 1 d . . . . .
C7 C 0.41181(10) 0.7635(2) 0.49276(17) 0.0201(5) Uani 1 1 d . . . . .
C8 C 0.47305(10) 0.8173(2) 0.40800(17) 0.0192(5) Uani 1 1 d . . . . .
S1 S 0.70827(3) 0.45032(7) 0.32008(5) 0.03341(18) Uani 1 1 d . . . . .
O5 O 0.66358(9) 0.4307(2) 0.37160(17) 0.0371(5) Uani 1 1 d . . . . .
C9 C 0.76659(14) 0.5443(4) 0.4086(3) 0.0504(8) Uani 1 1 d . . . . .
H9A H 0.753726 0.636334 0.409361 0.076 Uiso 1 1 calc GR . . . .
H9B H 0.800920 0.542120 0.387349 0.076 Uiso 1 1 calc GR . . . .
H9C H 0.777282 0.506118 0.477907 0.076 Uiso 1 1 calc GR . . . .
C10 C 0.74454(14) 0.2952(3) 0.3329(3) 0.0449(8) Uani 1 1 d . . . . .
H10A H 0.761063 0.270294 0.405957 0.067 Uiso 1 1 calc GR . . . .
H10B H 0.776408 0.302084 0.305475 0.067 Uiso 1 1 calc GR . . . .
H10C H 0.716238 0.227520 0.294203 0.067 Uiso 1 1 calc GR . . . .
O2 O 0.61419(10) 0.9418(2) 0.35087(19) 0.0463(6) Uani 1 1 d . . . . .
O3 O 0.67565(13) 1.0070(2) 0.2828(2) 0.0672(8) Uani 1 1 d . . . . .
O4 O 0.65927(10) 0.7988(2) 0.29089(19) 0.0447(6) Uani 1 1 d . . . . .
N7 N 0.65009(10) 0.9168(2) 0.30811(19) 0.0308(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O1 2.1239(16) . ?
Co1 O1 2.1240(16) 2_655 ?
Co1 N1 2.0851(19) 2_655 ?
Co1 N1 2.0851(19) . ?
Co1 N2 2.1730(18) . ?
Co1 N2 2.1730(18) 2_655 ?
O1 H1A 0.8760 . ?
O1 H1B 0.8768 . ?
C1 C1 1.480(5) 2_655 ?
C1 N1 1.341(3) . ?
C1 C2 1.390(3) . ?
N1 C5 1.337(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(4) . ?
N2 C6 1.350(3) . ?
N2 C8 1.359(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(4) . ?
N3 C7 1.343(3) . ?
N3 C8 1.344(3) . ?
N4 C6 1.311(3) . ?
N4 C7 1.368(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(3) . ?
C5 C6 1.488(3) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C8 1.333(3) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
N6 C7 1.328(3) . ?
S1 O5 1.5126(19) . ?
S1 C9 1.777(3) . ?
S1 C10 1.771(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
O2 N7 1.245(3) . ?
O3 N7 1.222(3) . ?
O4 N7 1.248(3) . ?

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 167.92(9) . 2_655 ?
O1 Co1 N2 88.04(7) 2_655 2_655 ?
O1 Co1 N2 87.43(7) . 2_655 ?
O1 Co1 N2 87.42(7) 2_655 . ?
O1 Co1 N2 88.05(7) . . ?
N1 Co1 O1 100.88(7) 2_655 2_655 ?
N1 Co1 O1 100.88(7) . . ?
N1 Co1 O1 88.79(7) . 2_655 ?
N1 Co1 O1 88.79(7) 2_655 . ?
N1 Co1 N1 74.47(10) 2_655 . ?
N1 Co1 N2 75.29(7) . . ?
N1 Co1 N2 75.29(7) 2_655 2_655 ?
N1 Co1 N2 148.40(7) 2_655 . ?
N1 Co1 N2 148.40(7) . 2_655 ?
N2 Co1 N2 135.90(10) 2_655 . ?
Co1 O1 H1A 110.5 . . ?
Co1 O1 H1B 111.0 . . ?
H1A O1 H1B 108.0 . . ?
N1 C1 C1 112.58(13) . 2_655 ?
N1 C1 C2 120.7(2) . . ?
C2 C1 C1 126.75(14) . 2_655 ?
C1 N1 Co1 119.59(15) . . ?
C5 N1 Co1 119.05(15) . . ?
C5 N1 C1 120.85(19) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.6(2) . . ?
C3 C2 H2 120.7 . . ?
C6 N2 Co1 114.29(14) . . ?
C6 N2 C8 113.78(19) . . ?
C8 N2 Co1 131.86(15) . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.3(2) . . ?
C4 C3 H3 119.8 . . ?
C7 N3 C8 115.3(2) . . ?
C6 N4 C7 114.3(2) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 C3 117.8(2) . . ?
C5 C4 H4 121.1 . . ?
N1 C5 C4 121.7(2) . . ?
N1 C5 C6 113.40(19) . . ?
C4 C5 C6 124.9(2) . . ?
H5A N5 H5B 120.0 . . ?
C8 N5 H5A 120.0 . . ?
C8 N5 H5B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C7 N6 H6A 120.0 . . ?
C7 N6 H6B 120.0 . . ?
N2 C6 C5 115.55(19) . . ?
N4 C6 N2 127.0(2) . . ?
N4 C6 C5 117.3(2) . . ?
N3 C7 N4 124.6(2) . . ?
N6 C7 N3 119.4(2) . . ?
N6 C7 N4 115.9(2) . . ?
N3 C8 N2 124.6(2) . . ?
N5 C8 N2 117.8(2) . . ?
N5 C8 N3 117.6(2) . . ?
O5 S1 C9 105.78(16) . . ?
O5 S1 C10 104.70(13) . . ?
C10 S1 C9 98.99(17) . . ?
S1 C9 H9A 109.5 . . ?
S1 C9 H9B 109.5 . . ?
S1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
S1 C10 H10A 109.5 . . ?
S1 C10 H10B 109.5 . . ?
S1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 N7 O4 119.2(2) . . ?
O3 N7 O2 120.2(2) . . ?
O3 N7 O4 120.6(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
_geom_hbond_publ_flag
O1 H1A O2 0.88 2.46 3.164(3) 138.0 . yes
O1 H1A O4 0.88 1.94 2.789(3) 164.3 . yes
O1 H1A N7 0.88 2.55 3.403(3) 166.5 . yes
O1 H1B S1 0.88 2.94 3.6667(18) 142.1 . yes
O1 H1B O5 0.88 1.86 2.727(3) 167.4 . yes
N5 H5A N3 0.88 2.24 3.059(3) 155.5 5_676 yes
N5 H5B O2 0.88 2.16 2.811(3) 130.6 . yes
N6 H6A O2 0.88 2.09 2.962(3) 173.2 5_676 yes
N6 H6B O5 0.88 2.03 2.878(3) 161.9 5_666 yes

_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_ada125
_database_code_depnum_ccdc_archive 'CCDC 1919280'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;University of Montreal
Canada
;
_audit_update_record             
;
2019-08-04 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;
_audit_creation_date             2019-08-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 Cu N13 O3, N O3, 0.5(C4 H8 O), 0.5(O)'
_chemical_formula_sum            'C18 H18 Cu N14 O7'
_chemical_formula_weight         606.00
_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 0.0137 0.0057 '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'
Cu Cu -2.7968 3.6874 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0390 0.0241 '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                   10.1245(3)
_cell_length_b                   15.8382(4)
_cell_length_c                   21.6268(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.018(1)
_cell_angle_gamma                90
_cell_volume                     3391.93(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    150
_cell_measurement_theta_max      60.793
_cell_measurement_theta_min      3.637
_shelx_estimated_absorpt_T_max   0.704
_shelx_estimated_absorpt_T_min   0.566
_exptl_absorpt_coefficient_mu    3.772
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.5942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1239 before and 0.0689 after correction. The Ratio of minimum to maximum transmission is 0.7903. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1236
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            49606
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.825
_diffrn_reflns_theta_min         3.032
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7080
_reflns_number_total             7797
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.933
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.138
_refine_ls_extinction_coef       0.0039(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         7797
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0677
_refine_ls_restrained_S_all      1.105
_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)+(0.1239P)²+5.0797P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2067
_refine_ls_wR_factor_ref         0.2110
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2. Restrained distances
 C1C-C2C \\sim C2C-C3C \\sim C3C-C4C
 with sigma of 0.02
 O1C-C1C \\sim O1C-C4C
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O2A) = Uanis(O2B)
4. Others
 Sof(O2B)=1-FVAR(1)
 Sof(O2A)=FVAR(1)
 Fixed Sof: C1C(0.5) H1CA(0.5) H1CB(0.5) C4C(0.5) H4CA(0.5) H4CB(0.5) O1C(0.5)
 O5C(0.5) C2C(0.5) H2CA(0.5) H2CB(0.5) C3C(0.5) H3CA(0.5) H3CB(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C1C(H1CA,H1CB), C4C(H4CA,H4CB), C2C(H2CA,H2CB), C3C(H3CA,H3CB)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C12(H12)
5.c X=CH2 refined with riding coordinates:
 N5(H5A,H5B), N6(H6A,H6B), N11(H11A,H11B), N12(H12A,H12B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5798(3) 0.88698(18) 0.68851(15) 0.0235(6) Uani 1 1 d . . . . .
C2 C 0.5584(3) 0.97274(19) 0.67943(17) 0.0290(7) Uani 1 1 d . . . . .
H2 H 0.618391 1.006256 0.661324 0.035 Uiso 1 1 calc R . . . .
C3 C 0.4477(3) 1.0085(2) 0.69737(19) 0.0357(8) Uani 1 1 d . . . . .
H3 H 0.430970 1.067225 0.691310 0.043 Uiso 1 1 calc R . . . .
C4 C 0.3607(3) 0.9597(2) 0.72402(19) 0.0352(8) Uani 1 1 d . . . . .
H4 H 0.284737 0.984124 0.736600 0.042 Uiso 1 1 calc R . . . .
C5 C 0.3881(3) 0.87410(18) 0.73181(15) 0.0253(6) Uani 1 1 d . . . . .
C6 C 0.3142(3) 0.81128(18) 0.76381(15) 0.0237(6) Uani 1 1 d . . . . .
C7 C 0.3236(3) 0.68401(18) 0.81343(14) 0.0223(5) Uani 1 1 d . . . . .
C8 C 0.1449(3) 0.77161(18) 0.81018(15) 0.0236(6) Uani 1 1 d . . . . .
C9 C 0.6930(3) 0.83648(18) 0.67490(14) 0.0224(6) Uani 1 1 d . . . . .
C10 C 0.8100(3) 0.8648(2) 0.65731(15) 0.0267(6) Uani 1 1 d . . . . .
H10 H 0.823845 0.923172 0.650849 0.032 Uiso 1 1 calc R . . . .
C11 C 0.9063(3) 0.8052(2) 0.64944(17) 0.0293(6) Uani 1 1 d . . . . .
H11 H 0.987551 0.823271 0.638121 0.035 Uiso 1 1 calc R . . . .
C12 C 0.8853(3) 0.71955(19) 0.65792(16) 0.0258(6) Uani 1 1 d . . . . .
H12 H 0.950406 0.678588 0.652394 0.031 Uiso 1 1 calc R . . . .
C13 C 0.7653(3) 0.69632(19) 0.67478(14) 0.0222(5) Uani 1 1 d . . . . .
C14 C 0.7196(3) 0.60866(18) 0.68309(14) 0.0221(5) Uani 1 1 d . . . . .
C15 C 0.5537(3) 0.52247(18) 0.70405(15) 0.0243(6) Uani 1 1 d . . . . .
C16 C 0.7400(3) 0.46807(19) 0.67495(14) 0.0241(6) Uani 1 1 d . . . . .
Cu1 Cu 0.52195(4) 0.71785(3) 0.72043(2) 0.02362(16) Uani 1 1 d . . . . .
N1 N 0.4929(3) 0.84050(15) 0.71361(12) 0.0224(5) Uani 1 1 d . . . . .
N2 N 0.3778(2) 0.73645(16) 0.77481(13) 0.0228(5) Uani 1 1 d . . . . .
N3 N 0.2058(3) 0.69858(16) 0.83034(13) 0.0240(5) Uani 1 1 d . . . . .
N4 N 0.1994(2) 0.83348(16) 0.77897(13) 0.0244(5) Uani 1 1 d . . . . .
N5 N 0.3929(3) 0.61524(16) 0.83465(13) 0.0272(5) Uani 1 1 d . . . . .
H5A H 0.361291 0.579959 0.859486 0.033 Uiso 1 1 calc R . . . .
H5B H 0.470483 0.604848 0.823922 0.033 Uiso 1 1 calc R . . . .
N6 N 0.0226(3) 0.78567(16) 0.82209(15) 0.0288(6) Uani 1 1 d . . . . .
H6A H -0.015164 0.747637 0.842506 0.035 Uiso 1 1 calc R . . . .
H6B H -0.020264 0.832976 0.809516 0.035 Uiso 1 1 calc R . . . .
N7 N 0.6745(2) 0.75346(16) 0.68354(12) 0.0218(5) Uani 1 1 d . . . . .
N8 N 0.6015(3) 0.60280(15) 0.70300(12) 0.0235(5) Uani 1 1 d . . . . .
N9 N 0.6227(3) 0.45340(16) 0.69301(12) 0.0243(5) Uani 1 1 d . . . . .
N10 N 0.7923(2) 0.54615(16) 0.66871(12) 0.0247(5) Uani 1 1 d . . . . .
N11 N 0.4315(3) 0.51200(17) 0.71670(16) 0.0351(7) Uani 1 1 d . . . . .
H11A H 0.397869 0.460902 0.717673 0.042 Uiso 1 1 calc R . . . .
H11B H 0.384399 0.556186 0.724089 0.042 Uiso 1 1 calc R . . . .
N12 N 0.8096(3) 0.40221(17) 0.66157(14) 0.0307(6) Uani 1 1 d . . . . .
H12A H 0.778808 0.350749 0.664612 0.037 Uiso 1 1 calc R . . . .
H12B H 0.886695 0.409905 0.649635 0.037 Uiso 1 1 calc R . . . .
N13 N 0.2311(3) 0.6793(2) 0.63695(16) 0.0371(7) Uani 1 1 d . . . . .
O1 O 0.3504(3) 0.6957(3) 0.63510(15) 0.0645(10) Uani 1 1 d . . . . .
O2A O 0.1363(5) 0.7048(5) 0.5928(3) 0.0635(17) Uani 0.717(9) 1 d . . P A 1
O2B O 0.1734(13) 0.7409(13) 0.6202(7) 0.0635(17) Uani 0.283(9) 1 d . . P A 2
O3 O 0.2022(3) 0.63035(18) 0.67741(15) 0.0459(7) Uani 1 1 d . . . . .
N14 N 0.7540(3) 0.65215(16) 0.84944(13) 0.0255(5) Uani 1 1 d . . . . .
O4 O 0.7003(3) 0.71870(14) 0.82405(14) 0.0368(6) Uani 1 1 d . . . . .
O5 O 0.6845(2) 0.58645(14) 0.84912(13) 0.0338(5) Uani 1 1 d . . . . .
O6 O 0.8757(2) 0.65142(16) 0.87468(14) 0.0379(6) Uani 1 1 d . . . . .
C1C C 0.5155(12) 0.7293(9) 0.5202(5) 0.074(3) Uani 0.5 1 d D . P B 1
H1CA H 0.559960 0.760204 0.490314 0.089 Uiso 0.5 1 calc R . P B 1
H1CB H 0.498690 0.769043 0.553072 0.089 Uiso 0.5 1 calc R . P B 1
C4C C 0.5329(14) 0.5851(10) 0.5414(5) 0.086(4) Uani 0.5 1 d D . P B 1
H4CA H 0.485769 0.574686 0.576421 0.103 Uiso 0.5 1 calc R . P B 1
H4CB H 0.596661 0.538245 0.539510 0.103 Uiso 0.5 1 calc R . P B 1
O1C O 0.5964(7) 0.6596(6) 0.5480(3) 0.069(2) Uani 0.5 1 d D . P B 1
O5C O 0.5191(8) 0.6620(8) 0.4953(3) 0.093(3) Uani 0.5 1 d . . P C 2
C2C C 0.3790(10) 0.6869(7) 0.4843(4) 0.059(3) Uani 0.5 1 d D . P B 1
H2CA H 0.308545 0.688276 0.509910 0.071 Uiso 0.5 1 calc R . P B 1
H2CB H 0.343997 0.713760 0.442774 0.071 Uiso 0.5 1 calc R . P B 1
C3C C 0.4304(14) 0.5958(8) 0.4771(5) 0.083(4) Uani 0.5 1 d D . P B 1
H3CA H 0.475457 0.591130 0.440749 0.099 Uiso 0.5 1 calc R . P B 1
H3CB H 0.356311 0.554000 0.472359 0.099 Uiso 0.5 1 calc R . P B 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.383(4) . ?
C1 C9 1.476(4) . ?
C1 N1 1.346(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(4) . ?
C5 C6 1.498(4) . ?
C5 N1 1.318(4) . ?
C6 N2 1.346(4) . ?
C6 N4 1.320(4) . ?
C7 N2 1.371(4) . ?
C7 N3 1.338(4) . ?
C7 N5 1.325(4) . ?
C8 N3 1.340(4) . ?
C8 N4 1.369(4) . ?
C8 N6 1.335(4) . ?
C9 C10 1.392(4) . ?
C9 N7 1.347(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.393(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.391(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.389(4) . ?
C13 C14 1.486(4) . ?
C13 N7 1.332(4) . ?
C14 N8 1.356(4) . ?
C14 N10 1.310(4) . ?
C15 N8 1.363(4) . ?
C15 N9 1.346(4) . ?
C15 N11 1.332(4) . ?
C16 N9 1.345(4) . ?
C16 N10 1.363(4) . ?
C16 N12 1.324(4) . ?
Cu1 N1 1.966(3) . ?
Cu1 N2 2.077(2) . ?
Cu1 N7 1.963(2) . ?
Cu1 N8 2.059(2) . ?
Cu1 O1 2.283(3) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
N11 H11A 0.8800 . ?
N11 H11B 0.8800 . ?
N12 H12A 0.8800 . ?
N12 H12B 0.8800 . ?
N13 O1 1.244(4) . ?
N13 O2A 1.271(6) . ?
N13 O2B 1.155(17) . ?
N13 O3 1.249(4) . ?
N14 O4 1.258(3) . ?
N14 O5 1.255(3) . ?
N14 O6 1.240(4) . ?
C1C H1CA 0.9900 . ?
C1C H1CB 0.9900 . ?
C1C O1C 1.432(14) . ?
C1C C2C 1.587(13) . ?
C4C H4CA 0.9900 . ?
C4C H4CB 0.9900 . ?
C4C O1C 1.336(15) . ?
C4C C3C 1.561(13) . ?
C2C H2CA 0.9900 . ?
C2C H2CB 0.9900 . ?
C2C C3C 1.553(13) . ?
C3C H3CA 0.9900 . ?
C3C H3CB 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C9 127.5(3) . . ?
N1 C1 C2 119.9(3) . . ?
N1 C1 C9 112.6(2) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.3(3) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 121.1 . . ?
C3 C4 C5 117.9(3) . . ?
C5 C4 H4 121.1 . . ?
C4 C5 C6 126.8(3) . . ?
N1 C5 C4 120.7(3) . . ?
N1 C5 C6 112.3(2) . . ?
N2 C6 C5 113.6(2) . . ?
N4 C6 C5 119.2(3) . . ?
N4 C6 N2 127.2(3) . . ?
N3 C7 N2 123.7(3) . . ?
N5 C7 N2 117.3(3) . . ?
N5 C7 N3 119.0(3) . . ?
N3 C8 N4 125.0(3) . . ?
N6 C8 N3 117.6(3) . . ?
N6 C8 N4 117.4(3) . . ?
C10 C9 C1 128.3(3) . . ?
N7 C9 C1 111.4(2) . . ?
N7 C9 C10 120.2(3) . . ?
C9 C10 H10 120.9 . . ?
C9 C10 C11 118.2(3) . . ?
C11 C10 H10 120.9 . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.0(3) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 121.3 . . ?
C13 C12 C11 117.3(3) . . ?
C13 C12 H12 121.3 . . ?
C12 C13 C14 126.2(3) . . ?
N7 C13 C12 121.7(3) . . ?
N7 C13 C14 112.1(2) . . ?
N8 C14 C13 114.8(2) . . ?
N10 C14 C13 118.2(3) . . ?
N10 C14 N8 126.9(3) . . ?
N9 C15 N8 123.8(3) . . ?
N11 C15 N8 117.9(3) . . ?
N11 C15 N9 118.3(3) . . ?
N9 C16 N10 124.8(3) . . ?
N12 C16 N9 118.0(3) . . ?
N12 C16 N10 117.2(3) . . ?
N1 Cu1 N2 77.91(10) . . ?
N1 Cu1 N8 156.81(10) . . ?
N1 Cu1 O1 90.82(14) . . ?
N2 Cu1 O1 88.47(11) . . ?
N7 Cu1 N1 78.68(10) . . ?
N7 Cu1 N2 153.44(11) . . ?
N7 Cu1 N8 78.99(10) . . ?
N7 Cu1 O1 104.25(11) . . ?
N8 Cu1 N2 125.24(10) . . ?
N8 Cu1 O1 88.68(14) . . ?
C1 N1 Cu1 118.1(2) . . ?
C5 N1 C1 122.3(3) . . ?
C5 N1 Cu1 119.6(2) . . ?
C6 N2 C7 113.8(2) . . ?
C6 N2 Cu1 113.03(19) . . ?
C7 N2 Cu1 132.6(2) . . ?
C7 N3 C8 115.8(3) . . ?
C6 N4 C8 113.4(3) . . ?
C7 N5 H5A 120.0 . . ?
C7 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C8 N6 H6A 120.0 . . ?
C8 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C9 N7 Cu1 118.7(2) . . ?
C13 N7 C9 121.6(2) . . ?
C13 N7 Cu1 119.2(2) . . ?
C14 N8 C15 114.1(2) . . ?
C14 N8 Cu1 113.70(19) . . ?
C15 N8 Cu1 132.0(2) . . ?
C16 N9 C15 115.7(3) . . ?
C14 N10 C16 114.4(2) . . ?
C15 N11 H11A 120.0 . . ?
C15 N11 H11B 120.0 . . ?
H11A N11 H11B 120.0 . . ?
C16 N12 H12A 120.0 . . ?
C16 N12 H12B 120.0 . . ?
H12A N12 H12B 120.0 . . ?
O1 N13 O2A 119.8(4) . . ?
O1 N13 O3 121.5(3) . . ?
O2B N13 O1 104.2(8) . . ?
O2B N13 O3 124.5(7) . . ?
O3 N13 O2A 118.2(4) . . ?
N13 O1 Cu1 125.9(3) . . ?
O5 N14 O4 120.1(3) . . ?
O6 N14 O4 119.9(3) . . ?
O6 N14 O5 119.9(3) . . ?
H1CA C1C H1CB 109.0 . . ?
O1C C1C H1CA 111.0 . . ?
O1C C1C H1CB 111.0 . . ?
O1C C1C C2C 104.0(9) . . ?
C2C C1C H1CA 111.0 . . ?
C2C C1C H1CB 111.0 . . ?
H4CA C4C H4CB 109.2 . . ?
O1C C4C H4CA 111.3 . . ?
O1C C4C H4CB 111.3 . . ?
O1C C4C C3C 102.5(9) . . ?
C3C C4C H4CA 111.3 . . ?
C3C C4C H4CB 111.3 . . ?
C4C O1C C1C 114.6(9) . . ?
C1C C2C H2CA 111.9 . . ?
C1C C2C H2CB 111.9 . . ?
H2CA C2C H2CB 109.6 . . ?
C3C C2C C1C 99.6(8) . . ?
C3C C2C H2CA 111.9 . . ?
C3C C2C H2CB 111.9 . . ?
C4C C3C H3CA 111.6 . . ?
C4C C3C H3CB 111.6 . . ?
C2C C3C C4C 100.7(9) . . ?
C2C C3C H3CA 111.6 . . ?
C2C C3C H3CB 111.6 . . ?
H3CA C3C H3CB 109.4 . . ?

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
_geom_hbond_publ_flag
N5 H5B O5 0.88 2.14 2.940(3) 150.5 . yes
N6 H6A O6 0.88 2.08 2.955(4) 169.6 1_455 yes
N6 H6B N9 0.88 2.17 3.021(4) 163.8 2_556 yes
N11 H11A N4 0.88 2.25 3.132(4) 176.7 2_546 yes
N11 H11B N5 0.88 2.55 3.122(4) 123.2 . yes
N11 H11B O3 0.88 2.24 2.967(4) 139.6 . yes
N12 H12A O4 0.88 2.11 2.927(3) 153.9 2_646 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.3(6) . . . . ?
C1 C9 C10 C11 177.3(3) . . . . ?
C1 C9 N7 C13 -179.0(3) . . . . ?
C1 C9 N7 Cu1 -7.1(3) . . . . ?
C2 C1 C9 C10 8.4(6) . . . . ?
C2 C1 C9 N7 -173.8(3) . . . . ?
C2 C1 N1 C5 -1.8(5) . . . . ?
C2 C1 N1 Cu1 176.2(2) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?
C3 C4 C5 C6 175.0(3) . . . . ?
C3 C4 C5 N1 -0.8(6) . . . . ?
C4 C5 C6 N2 -168.3(3) . . . . ?
C4 C5 C6 N4 10.6(5) . . . . ?
C4 C5 N1 C1 1.9(5) . . . . ?
C4 C5 N1 Cu1 -176.1(3) . . . . ?
C5 C6 N2 C7 169.4(3) . . . . ?
C5 C6 N2 Cu1 -18.2(3) . . . . ?
C5 C6 N4 C8 -177.5(3) . . . . ?
C6 C5 N1 C1 -174.5(3) . . . . ?
C6 C5 N1 Cu1 7.5(4) . . . . ?
C9 C1 C2 C3 -177.9(3) . . . . ?
C9 C1 N1 C5 176.9(3) . . . . ?
C9 C1 N1 Cu1 -5.0(3) . . . . ?
C9 C10 C11 C12 1.0(5) . . . . ?
C10 C9 N7 C13 -1.0(4) . . . . ?
C10 C9 N7 Cu1 171.0(2) . . . . ?
C10 C11 C12 C13 -0.3(5) . . . . ?
C11 C12 C13 C14 176.8(3) . . . . ?
C11 C12 C13 N7 -1.0(5) . . . . ?
C12 C13 C14 N8 176.7(3) . . . . ?
C12 C13 C14 N10 -5.7(5) . . . . ?
C12 C13 N7 C9 1.7(5) . . . . ?
C12 C13 N7 Cu1 -170.2(2) . . . . ?
C13 C14 N8 C15 173.5(3) . . . . ?
C13 C14 N8 Cu1 -2.8(3) . . . . ?
C13 C14 N10 C16 -177.1(3) . . . . ?
C14 C13 N7 C9 -176.4(3) . . . . ?
C14 C13 N7 Cu1 11.7(3) . . . . ?
N1 C1 C2 C3 0.7(5) . . . . ?
N1 C1 C9 C10 -170.3(3) . . . . ?
N1 C1 C9 N7 7.6(4) . . . . ?
N1 C5 C6 N2 7.8(4) . . . . ?
N1 C5 C6 N4 -173.3(3) . . . . ?
N2 C6 N4 C8 1.3(5) . . . . ?
N2 C7 N3 C8 -3.9(4) . . . . ?
N3 C7 N2 C6 10.7(4) . . . . ?
N3 C7 N2 Cu1 -159.8(2) . . . . ?
N3 C8 N4 C6 7.0(5) . . . . ?
N4 C6 N2 C7 -9.5(5) . . . . ?
N4 C6 N2 Cu1 163.0(3) . . . . ?
N4 C8 N3 C7 -5.7(5) . . . . ?
N5 C7 N2 C6 -169.4(3) . . . . ?
N5 C7 N2 Cu1 20.0(4) . . . . ?
N5 C7 N3 C8 176.3(3) . . . . ?
N6 C8 N3 C7 175.2(3) . . . . ?
N6 C8 N4 C6 -173.9(3) . . . . ?
N7 C9 C10 C11 -0.4(5) . . . . ?
N7 C13 C14 N8 -5.3(4) . . . . ?
N7 C13 C14 N10 172.3(3) . . . . ?
N8 C14 N10 C16 0.2(4) . . . . ?
N8 C15 N9 C16 -5.7(4) . . . . ?
N9 C15 N8 C14 6.8(4) . . . . ?
N9 C15 N8 Cu1 -177.9(2) . . . . ?
N9 C16 N10 C14 1.2(4) . . . . ?
N10 C14 N8 C15 -3.9(5) . . . . ?
N10 C14 N8 Cu1 179.9(2) . . . . ?
N10 C16 N9 C15 1.4(4) . . . . ?
N11 C15 N8 C14 -173.2(3) . . . . ?
N11 C15 N8 Cu1 2.2(5) . . . . ?
N11 C15 N9 C16 174.3(3) . . . . ?
N12 C16 N9 C15 -177.9(3) . . . . ?
N12 C16 N10 C14 -179.5(3) . . . . ?
O2A N13 O1 Cu1 148.1(5) . . . . ?
O2B N13 O1 Cu1 107.0(10) . . . . ?
O3 N13 O1 Cu1 -40.2(6) . . . . ?
C1C C2C C3C C4C 37.3(11) . . . . ?
O1C C1C C2C C3C -21.5(10) . . . . ?
O1C C4C C3C C2C -42.6(12) . . . . ?
C2C C1C O1C C4C -5.9(11) . . . . ?
C3C C4C O1C C1C 30.7(12) . . . . ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 328 electrons were 
found in a volume of 1146Å^3 in 2 voids per unit cell.
This is consistent with the presence of 
a total of 7.8 DMSO (328 electrons) per unit, 
so around 2 DMSO per formula unit.
;

loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.348 -0.344 0.500 573.1 163.8 4*C2H6SO
2 -0.473 -0.224 0.000 573.1 163.8 4*C2H6SO

_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_ada127
_database_code_depnum_ccdc_archive 'CCDC 1919279'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;University of Montreal
Canada
;
_audit_update_record             
;
2019-08-04 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;
_audit_creation_date             2019-08-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C16 H16 N13 Ni O4), 2(N O3)'
_chemical_formula_sum            'C32 H32 N28 Ni2 O14'
_chemical_formula_weight         1150.27
_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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni -1.3355 3.2903 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6118(5)
_cell_length_b                   11.7609(6)
_cell_length_c                   14.1181(8)
_cell_angle_alpha                95.139(3)
_cell_angle_beta                 91.020(3)
_cell_angle_gamma                113.356(2)
_cell_volume                     1456.81(14)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    150
_cell_measurement_theta_max      55.056
_cell_measurement_theta_min      2.741
_shelx_estimated_absorpt_T_max   0.797
_shelx_estimated_absorpt_T_min   0.588
_exptl_absorpt_coefficient_mu    3.961
_exptl_absorpt_correction_T_max  0.3027
_exptl_absorpt_correction_T_min  0.2118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1511 before and 0.0773 after correction. The Ratio of minimum to maximum transmission is 0.6997. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21341
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.837
_diffrn_reflns_theta_min         2.739
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5349
_reflns_number_total             6685
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.0052(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         6685
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0554
_refine_ls_restrained_S_all      1.045
_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)+(0.0691P)²+1.0459P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1483
_refine_ls_wR_factor_ref         0.1569
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Rotating group:
 O4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C12(H12)
2.c X=CH2 refined with riding coordinates:
 N5(H5A,H5B), N6(H6A,H6B), N11(H11A,H11B), N12(H12A,H12B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
Ni1 Ni 0.65505(4) 0.79914(4) 0.83881(3) 0.03918(14) Uani 1 1 d . . . . .
C1 C 0.9780(3) 0.8851(3) 0.8903(2) 0.0434(7) Uani 1 1 d . . . . .
O1 O 0.6744(2) 0.97164(19) 0.90102(18) 0.0500(5) Uani 1 1 d . . . . .
N1 N 0.8808(3) 0.8848(2) 0.8210(2) 0.0418(6) Uani 1 1 d . . . . .
C2 C 1.1340(3) 0.9477(3) 0.8830(3) 0.0484(8) Uani 1 1 d . . . . .
H2 H 1.204067 0.947280 0.931191 0.058 Uiso 1 1 calc R . . . .
N2 N 0.6638(3) 0.8556(2) 0.6957(2) 0.0474(6) Uani 1 1 d . . . . .
O2 O 0.4862(3) 0.9702(3) 0.8122(3) 0.0781(9) Uani 1 1 d . . . . .
O3 O 0.6122(4) 1.1278(3) 0.9161(3) 0.0954(11) Uani 1 1 d . . . . .
N3 N 0.5790(4) 0.9022(3) 0.5498(3) 0.0660(9) Uani 1 1 d . . . . .
C3 C 1.1839(4) 1.0101(3) 0.8039(3) 0.0564(9) Uani 1 1 d . . . . .
H3 H 1.289761 1.053395 0.797633 0.068 Uiso 1 1 calc R . . . .
O4 O 0.6376(3) 0.62490(19) 0.77975(16) 0.0483(5) Uani 1 1 d . . . . .
H4A H 0.696977 0.630480 0.730881 0.072 Uiso 1 1 d GR . . . .
H4B H 0.542877 0.576333 0.757708 0.072 Uiso 1 1 d GR . . . .
C4 C 1.0820(4) 1.0107(3) 0.7336(3) 0.0534(8) Uani 1 1 d . . . . .
H4 H 1.116299 1.054350 0.679474 0.064 Uiso 1 1 calc R . . . .
N4 N 0.8403(3) 0.9994(3) 0.6012(2) 0.0530(7) Uani 1 1 d . . . . .
N5 N 0.4188(4) 0.7484(3) 0.6303(3) 0.0739(10) Uani 1 1 d . . . . .
H5A H 0.347899 0.734771 0.585273 0.089 Uiso 1 1 calc R . . . .
H5B H 0.398653 0.703203 0.678678 0.089 Uiso 1 1 calc R . . . .
C5 C 0.9287(3) 0.9458(3) 0.7446(2) 0.0444(7) Uani 1 1 d . . . . .
N6 N 0.7426(5) 1.0526(4) 0.4690(3) 0.0866(12) Uani 1 1 d . . . . .
H6A H 0.666610 1.042976 0.429009 0.104 Uiso 1 1 calc R . . . .
H6B H 0.834327 1.107864 0.461119 0.104 Uiso 1 1 calc R . . . .
C6 C 0.8030(4) 0.9343(3) 0.6758(3) 0.0470(7) Uani 1 1 d . . . . .
C7 C 0.5564(4) 0.8373(3) 0.6253(3) 0.0566(9) Uani 1 1 d . . . . .
N7 N 0.7490(3) 0.7726(2) 0.95918(19) 0.0403(5) Uani 1 1 d . . . . .
N8 N 0.4593(3) 0.7033(2) 0.91707(19) 0.0415(6) Uani 1 1 d . . . . .
C8 C 0.7187(4) 0.9829(3) 0.5422(3) 0.0610(9) Uani 1 1 d . . . . .
N9 N 0.2002(3) 0.5972(2) 0.9534(2) 0.0452(6) Uani 1 1 d . . . . .
C9 C 0.9017(3) 0.8145(3) 0.9696(2) 0.0416(7) Uani 1 1 d . . . . .
N10 N 0.4013(3) 0.5967(2) 1.0560(2) 0.0451(6) Uani 1 1 d . . . . .
C10 C 0.9706(4) 0.7888(3) 1.0471(3) 0.0496(8) Uani 1 1 d . . . . .
H10 H 1.078011 0.819430 1.055304 0.060 Uiso 1 1 calc R . . . .
N11 N 0.2636(3) 0.7116(3) 0.8262(2) 0.0611(8) Uani 1 1 d . . . . .
H11A H 0.166602 0.691787 0.812487 0.073 Uiso 1 1 calc R . . . .
H11B H 0.332305 0.759516 0.790531 0.073 Uiso 1 1 calc R . . . .
C11 C 0.8786(4) 0.7173(3) 1.1122(3) 0.0521(8) Uani 1 1 d . . . . .
H11 H 0.923390 0.697333 1.165360 0.063 Uiso 1 1 calc R . . . .
N12 N 0.1516(3) 0.4908(3) 1.0858(2) 0.0552(7) Uani 1 1 d . . . . .
H12A H 0.053626 0.466643 1.072558 0.066 Uiso 1 1 calc R . . . .
H12B H 0.183640 0.467392 1.136372 0.066 Uiso 1 1 calc R . . . .
C12 C 0.7204(4) 0.6738(3) 1.1009(3) 0.0504(8) Uani 1 1 d . . . . .
H12 H 0.656443 0.625336 1.145626 0.060 Uiso 1 1 calc R . . . .
N13 N 0.5890(3) 1.0241(3) 0.8765(3) 0.0604(8) Uani 1 1 d . . . . .
C13 C 0.6610(3) 0.7043(3) 1.0219(2) 0.0427(7) Uani 1 1 d . . . . .
C14 C 0.4950(3) 0.6651(3) 0.9979(2) 0.0422(7) Uani 1 1 d . . . . .
C15 C 0.2509(3) 0.5625(3) 1.0297(2) 0.0454(7) Uani 1 1 d . . . . .
C16 C 0.3061(3) 0.6696(3) 0.9002(3) 0.0450(7) Uani 1 1 d . . . . .
N14 N 0.9541(4) 0.6762(3) 0.6679(2) 0.0584(7) Uani 1 1 d . . . . .
O5 O 1.0708(4) 0.7284(3) 0.6259(3) 0.0805(9) Uani 1 1 d . . . . .
O6 O 0.8309(3) 0.6755(3) 0.6361(2) 0.0710(7) Uani 1 1 d . . . . .
O7 O 0.9561(3) 0.6275(3) 0.7428(2) 0.0699(7) 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
Ni1 O1 2.073(2) . ?
Ni1 N1 2.029(2) . ?
Ni1 N2 2.176(3) . ?
Ni1 O4 2.083(2) . ?
Ni1 N7 2.016(3) . ?
Ni1 N8 2.156(3) . ?
C1 N1 1.340(4) . ?
C1 C2 1.395(4) . ?
C1 C9 1.481(5) . ?
O1 N13 1.266(4) . ?
N1 C5 1.336(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.379(5) . ?
N2 C6 1.343(4) . ?
N2 C7 1.359(4) . ?
O2 N13 1.254(4) . ?
O3 N13 1.229(4) . ?
N3 C7 1.338(5) . ?
N3 C8 1.314(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(5) . ?
O4 H4A 0.8938 . ?
O4 H4B 0.8929 . ?
C4 H4 0.9500 . ?
C4 C5 1.384(4) . ?
N4 C6 1.328(5) . ?
N4 C8 1.362(5) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C7 1.329(5) . ?
C5 C6 1.492(5) . ?
N6 H6A 0.8800 . ?
N6 H6B 0.8800 . ?
N6 C8 1.343(5) . ?
N7 C9 1.351(4) . ?
N7 C13 1.326(4) . ?
N8 C14 1.349(4) . ?
N8 C16 1.375(4) . ?
N9 C15 1.335(4) . ?
N9 C16 1.334(4) . ?
C9 C10 1.386(5) . ?
N10 C14 1.305(4) . ?
N10 C15 1.372(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(5) . ?
N11 H11A 0.8800 . ?
N11 H11B 0.8800 . ?
N11 C16 1.318(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.400(5) . ?
N12 H12A 0.8800 . ?
N12 H12B 0.8800 . ?
N12 C15 1.326(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.382(5) . ?
C13 C14 1.498(4) . ?
N14 O5 1.237(4) . ?
N14 O6 1.255(4) . ?
N14 O7 1.251(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
O1 Ni1 N2 92.65(10) . . ?
O1 Ni1 O4 178.47(9) . . ?
O1 Ni1 N8 92.00(9) . . ?
N1 Ni1 O1 85.36(9) . . ?
N1 Ni1 N2 76.50(11) . . ?
N1 Ni1 O4 94.46(9) . . ?
N1 Ni1 N8 154.59(11) . . ?
O4 Ni1 N2 88.77(10) . . ?
O4 Ni1 N8 87.52(9) . . ?
N7 Ni1 O1 89.70(10) . . ?
N7 Ni1 N1 77.25(11) . . ?
N7 Ni1 N2 153.36(10) . . ?
N7 Ni1 O4 88.78(9) . . ?
N7 Ni1 N8 77.47(10) . . ?
N8 Ni1 N2 128.90(10) . . ?
N1 C1 C2 120.2(3) . . ?
N1 C1 C9 113.2(3) . . ?
C2 C1 C9 126.6(3) . . ?
N13 O1 Ni1 123.2(2) . . ?
C1 N1 Ni1 118.3(2) . . ?
C5 N1 Ni1 119.8(2) . . ?
C5 N1 C1 121.7(3) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 H2 120.9 . . ?
C6 N2 Ni1 113.1(2) . . ?
C6 N2 C7 113.0(3) . . ?
C7 N2 Ni1 133.7(2) . . ?
C8 N3 C7 115.8(3) . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.9(3) . . ?
C4 C3 H3 119.5 . . ?
Ni1 O4 H4A 112.0 . . ?
Ni1 O4 H4B 111.8 . . ?
H4A O4 H4B 106.8 . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 118.1(3) . . ?
C5 C4 H4 121.0 . . ?
C6 N4 C8 113.2(3) . . ?
H5A N5 H5B 120.0 . . ?
C7 N5 H5A 120.0 . . ?
C7 N5 H5B 120.0 . . ?
N1 C5 C4 120.8(3) . . ?
N1 C5 C6 113.6(3) . . ?
C4 C5 C6 125.6(3) . . ?
H6A N6 H6B 120.0 . . ?
C8 N6 H6A 120.0 . . ?
C8 N6 H6B 120.0 . . ?
N2 C6 C5 115.4(3) . . ?
N4 C6 N2 127.3(3) . . ?
N4 C6 C5 117.3(3) . . ?
N3 C7 N2 124.6(3) . . ?
N5 C7 N2 118.6(4) . . ?
N5 C7 N3 116.7(3) . . ?
C9 N7 Ni1 118.7(2) . . ?
C13 N7 Ni1 119.89(19) . . ?
C13 N7 C9 121.0(3) . . ?
C14 N8 Ni1 112.87(19) . . ?
C14 N8 C16 113.7(3) . . ?
C16 N8 Ni1 133.4(2) . . ?
N3 C8 N4 125.4(4) . . ?
N3 C8 N6 116.8(4) . . ?
N6 C8 N4 117.9(4) . . ?
C16 N9 C15 116.1(3) . . ?
N7 C9 C1 112.3(3) . . ?
N7 C9 C10 120.7(3) . . ?
C10 C9 C1 127.0(3) . . ?
C14 N10 C15 114.2(3) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 C9 118.2(3) . . ?
C11 C10 H10 120.9 . . ?
H11A N11 H11B 120.0 . . ?
C16 N11 H11A 120.0 . . ?
C16 N11 H11B 120.0 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
H12A N12 H12B 120.0 . . ?
C15 N12 H12A 120.0 . . ?
C15 N12 H12B 120.0 . . ?
C11 C12 H12 121.4 . . ?
C13 C12 C11 117.3(3) . . ?
C13 C12 H12 121.4 . . ?
O2 N13 O1 119.5(3) . . ?
O3 N13 O1 118.2(3) . . ?
O3 N13 O2 122.3(3) . . ?
N7 C13 C12 122.0(3) . . ?
N7 C13 C14 113.4(3) . . ?
C12 C13 C14 124.6(3) . . ?
N8 C14 C13 115.8(3) . . ?
N10 C14 N8 127.3(3) . . ?
N10 C14 C13 116.9(3) . . ?
N9 C15 N10 124.6(3) . . ?
N12 C15 N9 119.2(3) . . ?
N12 C15 N10 116.2(3) . . ?
N9 C16 N8 123.9(3) . . ?
N11 C16 N8 117.0(3) . . ?
N11 C16 N9 119.1(3) . . ?
O5 N14 O6 119.1(3) . . ?
O5 N14 O7 121.9(3) . . ?
O7 N14 O6 119.0(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
_geom_hbond_publ_flag
O4 H4A N14 0.89 2.51 3.316(4) 150.5 . yes
O4 H4A O6 0.89 1.84 2.719(4) 168.6 . yes
O4 H4A O7 0.89 2.51 3.104(4) 124.6 . yes
N5 H5B N11 0.88 2.49 3.148(5) 132.2 . yes
N6 H6A N3 0.88 2.70 3.348(5) 131.7 2_676 yes
N6 H6B O5 0.88 2.26 2.948(5) 134.6 2_776 yes
N11 H11A O7 0.88 2.05 2.907(4) 163.2 1_455 yes
N11 H11B O2 0.88 2.32 2.971(4) 131.3 . yes
N11 H11B N5 0.88 2.43 3.148(5) 138.5 . yes
N12 H12A N9 0.88 2.26 3.141(4) 177.0 2_567 yes
N12 H12B O7 0.88 2.28 2.900(4) 127.5 2_667 yes


_platon_squeeze_details          
;
A solvent mask was calculated and 174 electrons were 
found in a volume of 438Å^3 per unit cell.
This is consistent with the presence of 
a total of 4 DMSO per unit-cell 
and formula unit (Z=1).
;



loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.086 0.500 0.500 438 174 4*C2H6SO

_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'




