# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 2330320'
loop_
_audit_author_name
_audit_author_address
'Christopher Ziegler'
;University of Akron
United States of America
;
_audit_update_record             
;
2024-02-01 deposited with the CCDC.	2024-05-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H29 N11 O'
_chemical_formula_weight         643.71

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

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

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

_cell_length_a                   6.029(4)
_cell_length_b                   15.799(11)
_cell_length_c                   16.468(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.653(14)
_cell_angle_gamma                90
_cell_volume                     1568.0(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9950
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      28.25

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.288
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.114
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6977
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35261
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.787
_diffrn_reflns_theta_max         28.362
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7788
_reflns_number_gt                6282
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.990
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.998

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0974P)²+0.1947P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2709 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.1(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7788
_refine_ls_number_parameters     444
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1502
_refine_ls_wR_factor_gt          0.1421
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5314(6) 0.9998(2) 0.5830(2) 0.0135(8) Uani 1 1 d . . . . .
C2 C 0.3421(7) 1.0496(2) 0.5501(2) 0.0140(8) Uani 1 1 d . . . . .
C3 C 0.1703(7) 1.0923(3) 0.5864(3) 0.0185(9) Uani 1 1 d . . . . .
H3 H 0.159911 1.093274 0.643810 0.022 Uiso 1 1 calc R U . . .
C4 C 0.0164(7) 1.1330(2) 0.5381(2) 0.0186(9) Uani 1 1 d . . . . .
H4 H -0.101330 1.162727 0.562470 0.022 Uiso 1 1 calc R U . . .
C5 C 0.0291(7) 1.1317(3) 0.4518(2) 0.0170(9) Uani 1 1 d . . . . .
H5 H -0.081243 1.159535 0.419251 0.020 Uiso 1 1 calc R U . . .
C6 C 0.2053(7) 1.0890(2) 0.4144(2) 0.0165(9) Uani 1 1 d . . . . .
H38 H 0.217028 1.088260 0.356959 0.020 Uiso 1 1 calc R U . . .
C7 C 0.3607(7) 1.0482(2) 0.4645(2) 0.0116(8) Uani 1 1 d . . . . .
C8 C 0.5632(7) 0.9979(3) 0.4511(2) 0.0150(9) Uani 1 1 d . . . . .
C9 C 0.6630(7) 0.9822(2) 0.3783(2) 0.0121(8) Uani 1 1 d . . . . .
C10 C 0.5766(7) 1.0192(2) 0.3060(2) 0.0152(8) Uani 1 1 d . . . . .
C11 C 0.8589(7) 0.9310(2) 0.3702(2) 0.0130(8) Uani 1 1 d . . . . .
C12 C 1.1506(7) 0.8529(2) 0.4033(2) 0.0148(8) Uani 1 1 d . . . . .
C13 C 1.3171(7) 0.8060(2) 0.4404(3) 0.0173(9) Uani 1 1 d . . . . .
H13 H 1.321469 0.796282 0.497331 0.021 Uiso 1 1 calc R U . . .
C14 C 1.4787(7) 0.7735(3) 0.3904(2) 0.0214(9) Uani 1 1 d . . . . .
H14 H 1.598924 0.741939 0.413479 0.026 Uiso 1 1 calc R U . . .
C15 C 1.4652(7) 0.7872(3) 0.3058(3) 0.0212(9) Uani 1 1 d . . . . .
H15 H 1.575108 0.763188 0.272685 0.025 Uiso 1 1 calc R U . . .
C16 C 1.2974(7) 0.8345(2) 0.2699(2) 0.0155(8) Uani 1 1 d . . . . .
H16 H 1.290995 0.843635 0.212842 0.019 Uiso 1 1 calc R U . . .
C17 C 1.1400(7) 0.8678(2) 0.3190(2) 0.0156(9) Uani 1 1 d . . . . .
C18 C 0.4652(7) 0.5036(2) 0.3228(2) 0.0150(8) Uani 1 1 d . . . . .
C19 C 0.6538(7) 0.5527(2) 0.3555(2) 0.0134(8) Uani 1 1 d . . . . .
C20 C 0.8250(7) 0.5936(2) 0.3175(2) 0.0167(9) Uani 1 1 d . . . . .
H20 H 0.837650 0.593147 0.260132 0.020 Uiso 1 1 calc R U . . .
C21 C 0.9803(7) 0.6361(2) 0.3691(3) 0.0189(9) Uani 1 1 d . . . . .
H21 H 1.100831 0.665716 0.346425 0.023 Uiso 1 1 calc R U . . .
C22 C 0.9574(7) 0.6347(2) 0.4511(3) 0.0185(9) Uani 1 1 d . . . . .
H22 H 1.063382 0.663888 0.484433 0.022 Uiso 1 1 calc R U . . .
C23 C 0.7871(7) 0.5927(2) 0.4876(2) 0.0159(9) Uani 1 1 d . . . . .
H23 H 0.776491 0.592122 0.545054 0.019 Uiso 1 1 calc R U . . .
C24 C 0.6329(7) 0.5517(2) 0.4389(2) 0.0152(9) Uani 1 1 d . . . . .
C25 C 0.4297(7) 0.5011(2) 0.4535(2) 0.0116(8) Uani 1 1 d . . . . .
C26 C 0.3349(7) 0.4842(2) 0.5258(2) 0.0138(8) Uani 1 1 d . . . . .
C27 C 0.4198(7) 0.5201(2) 0.6002(2) 0.0138(8) Uani 1 1 d . . . . .
C28 C 0.1338(7) 0.4333(2) 0.5327(2) 0.0125(8) Uani 1 1 d . . . . .
C29 C -0.1512(6) 0.3541(2) 0.4964(2) 0.0147(8) Uani 1 1 d . . . . .
C30 C -0.3221(7) 0.3086(2) 0.4574(3) 0.0182(9) Uani 1 1 d . . . . .
H30 H -0.330312 0.301888 0.400113 0.022 Uiso 1 1 calc R U . . .
C31 C -0.4790(7) 0.2739(2) 0.5075(2) 0.0200(9) Uani 1 1 d . . . . .
H31 H -0.594772 0.240489 0.483764 0.024 Uiso 1 1 calc R U . . .
C32 C -0.4735(7) 0.2859(2) 0.5908(3) 0.0211(9) Uani 1 1 d . . . . .
H32 H -0.587912 0.262166 0.622144 0.025 Uiso 1 1 calc R U . . .
C33 C -0.3053(7) 0.3317(3) 0.6298(2) 0.0214(10) Uani 1 1 d . . . . .
H33 H -0.300949 0.339171 0.687016 0.026 Uiso 1 1 calc R U . . .
C34 C -0.1399(7) 0.3669(2) 0.5801(2) 0.0133(8) Uani 1 1 d . . . . .
C35 C 0.8001(8) 0.7853(3) 0.6209(3) 0.0427(11) Uani 1 1 d . . . . .
H35 H 0.688937 0.806011 0.583973 0.051 Uiso 1 1 calc R U . . .
C36 C 0.8987(10) 0.7343(3) 0.7549(4) 0.0525(13) Uani 1 1 d . . . . .
H36A H 0.928184 0.782517 0.791095 0.079 Uiso 1 1 calc R U . . .
H36B H 1.036035 0.717847 0.728703 0.079 Uiso 1 1 calc R U . . .
H36C H 0.843454 0.686598 0.786484 0.079 Uiso 1 1 calc R U . . .
C37 C 0.5089(10) 0.7629(4) 0.7164(4) 0.0669(18) Uani 1 1 d . . . . .
H37A H 0.414571 0.778157 0.669180 0.100 Uiso 1 1 calc R U . . .
H37B H 0.494636 0.806024 0.758738 0.100 Uiso 1 1 calc R U . . .
H37C H 0.462410 0.707881 0.737444 0.100 Uiso 1 1 calc R U . . .
N1 N 0.5766(6) 0.9875(2) 0.65921(19) 0.0196(8) Uani 1 1 d . . . . .
H1A H 0.692870 0.956975 0.674225 0.023 Uiso 1 1 calc R U . . .
H1B H 0.491204 1.009531 0.696129 0.023 Uiso 1 1 calc R U . . .
N2 N 0.6532(6) 0.9684(2) 0.52249(18) 0.0141(7) Uani 1 1 d . . . . .
N3 N 0.9683(5) 0.8927(2) 0.43409(18) 0.0125(7) Uani 1 1 d . . . . .
H37 H 0.929389 0.893361 0.485183 0.015 Uiso 1 1 calc R U . . .
N4 N 0.9534(6) 0.9180(2) 0.29978(19) 0.0151(8) Uani 1 1 d . . . . .
N5 N 0.5104(6) 1.0504(2) 0.24704(19) 0.0192(8) Uani 1 1 d . . . . .
N6 N 0.4168(6) 0.4927(2) 0.24415(19) 0.0175(7) Uani 1 1 d . . . . .
H6A H 0.297588 0.464073 0.228824 0.021 Uiso 1 1 calc R U . . .
H6B H 0.503981 0.514145 0.207469 0.021 Uiso 1 1 calc R U . . .
N7 N 0.3402(6) 0.4728(2) 0.37988(19) 0.0149(7) Uani 1 1 d . . . . .
N8 N 0.0283(5) 0.3979(2) 0.4679(2) 0.0157(7) Uani 1 1 d . . . . .
H8 H 0.066820 0.401946 0.416877 0.019 Uiso 1 1 calc R U . . .
N9 N 0.0379(5) 0.41666(19) 0.60247(18) 0.0127(7) Uani 1 1 d . . . . .
N10 N 0.4846(6) 0.5497(2) 0.6599(2) 0.0225(8) Uani 1 1 d . . . . .
N11 N 0.7328(8) 0.7582(3) 0.6931(3) 0.0398(10) Uani 1 1 d . . . . .
O1 O 0.9945(7) 0.7859(2) 0.5974(2) 0.0576(10) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.291(5) . ?
C1 N2 1.350(5) . ?
C1 C2 1.476(6) . ?
C2 C3 1.386(6) . ?
C2 C7 1.417(5) . ?
C3 C4 1.365(6) . ?
C4 C5 1.426(6) . ?
C5 C6 1.414(5) . ?
C6 C7 1.390(6) . ?
C7 C8 1.479(6) . ?
C8 N2 1.362(5) . ?
C8 C9 1.379(5) . ?
C9 C10 1.412(5) . ?
C9 C11 1.441(6) . ?
C10 N5 1.151(5) . ?
C11 N4 1.322(5) . ?
C11 N3 1.368(5) . ?
C12 N3 1.376(5) . ?
C12 C13 1.376(6) . ?
C12 C17 1.408(5) . ?
C13 C14 1.391(5) . ?
C14 C15 1.410(6) . ?
C15 C16 1.377(6) . ?
C16 C17 1.370(5) . ?
C17 N4 1.405(5) . ?
C18 N7 1.315(5) . ?
C18 N6 1.330(5) . ?
C18 C19 1.466(6) . ?
C19 C20 1.382(5) . ?
C19 C24 1.383(5) . ?
C20 C21 1.416(6) . ?
C21 C22 1.362(6) . ?
C22 C23 1.375(6) . ?
C23 C24 1.373(6) . ?
C24 C25 1.488(6) . ?
C25 C26 1.362(5) . ?
C25 N7 1.387(5) . ?
C26 C27 1.432(6) . ?
C26 C28 1.462(6) . ?
C27 N10 1.147(5) . ?
C28 N9 1.328(4) . ?
C28 N8 1.348(5) . ?
C29 N8 1.378(5) . ?
C29 C34 1.393(5) . ?
C29 C30 1.397(6) . ?
C30 C31 1.386(6) . ?
C31 C32 1.384(6) . ?
C32 C33 1.388(6) . ?
C33 C34 1.421(5) . ?
C34 N9 1.371(5) . ?
C35 O1 1.245(6) . ?
C35 N11 1.338(6) . ?
C36 N11 1.456(7) . ?
C37 N11 1.416(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N2 123.9(4) . . ?
N1 C1 C2 125.3(3) . . ?
N2 C1 C2 110.8(3) . . ?
C3 C2 C7 121.2(4) . . ?
C3 C2 C1 132.8(4) . . ?
C7 C2 C1 106.0(3) . . ?
C4 C3 C2 118.8(4) . . ?
C3 C4 C5 121.2(4) . . ?
C6 C5 C4 120.2(4) . . ?
C7 C6 C5 117.7(4) . . ?
C6 C7 C2 120.9(4) . . ?
C6 C7 C8 134.9(4) . . ?
C2 C7 C8 104.2(3) . . ?
N2 C8 C9 121.1(4) . . ?
N2 C8 C7 111.4(3) . . ?
C9 C8 C7 127.5(4) . . ?
C8 C9 C10 120.0(4) . . ?
C8 C9 C11 124.1(4) . . ?
C10 C9 C11 115.9(3) . . ?
N5 C10 C9 178.5(5) . . ?
N4 C11 N3 113.3(3) . . ?
N4 C11 C9 123.0(3) . . ?
N3 C11 C9 123.7(3) . . ?
N3 C12 C13 131.6(3) . . ?
N3 C12 C17 105.8(3) . . ?
C13 C12 C17 122.6(4) . . ?
C12 C13 C14 116.8(4) . . ?
C13 C14 C15 120.4(4) . . ?
C16 C15 C14 121.9(4) . . ?
C17 C16 C15 117.8(4) . . ?
C16 C17 C12 120.4(4) . . ?
C16 C17 N4 130.3(4) . . ?
C12 C17 N4 109.3(3) . . ?
N7 C18 N6 122.3(4) . . ?
N7 C18 C19 112.8(3) . . ?
N6 C18 C19 124.9(4) . . ?
C20 C19 C24 123.0(4) . . ?
C20 C19 C18 131.5(4) . . ?
C24 C19 C18 105.5(3) . . ?
C19 C20 C21 116.1(4) . . ?
C22 C21 C20 120.2(4) . . ?
C21 C22 C23 122.7(4) . . ?
C24 C23 C22 118.3(4) . . ?
C23 C24 C19 119.7(4) . . ?
C23 C24 C25 134.9(4) . . ?
C19 C24 C25 105.4(4) . . ?
C26 C25 N7 122.6(4) . . ?
C26 C25 C24 128.0(4) . . ?
N7 C25 C24 109.5(3) . . ?
C25 C26 C27 121.5(4) . . ?
C25 C26 C28 123.1(4) . . ?
C27 C26 C28 115.3(3) . . ?
N10 C27 C26 178.9(5) . . ?
N9 C28 N8 113.3(3) . . ?
N9 C28 C26 124.0(4) . . ?
N8 C28 C26 122.7(3) . . ?
N8 C29 C34 104.4(3) . . ?
N8 C29 C30 132.6(4) . . ?
C34 C29 C30 122.9(3) . . ?
C31 C30 C29 115.9(4) . . ?
C32 C31 C30 122.6(4) . . ?
C31 C32 C33 121.7(4) . . ?
C32 C33 C34 117.0(4) . . ?
N9 C34 C29 111.3(3) . . ?
N9 C34 C33 128.8(4) . . ?
C29 C34 C33 119.8(4) . . ?
O1 C35 N11 126.3(5) . . ?
C1 N2 C8 107.5(3) . . ?
C11 N3 C12 107.0(3) . . ?
C11 N4 C17 104.6(3) . . ?
C18 N7 C25 106.8(3) . . ?
C28 N8 C29 107.2(3) . . ?
C28 N9 C34 103.8(3) . . ?
C35 N11 C37 122.7(5) . . ?
C35 N11 C36 119.0(5) . . ?
C37 N11 C36 117.7(5) . . ?

_refine_diff_density_max         0.531
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.060



####################################################################### 
# 
# 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_CuHlp
_database_code_depnum_ccdc_archive 'CCDC 2330321'
loop_
_audit_author_name
_audit_author_address
'Christopher Ziegler'
;University of Akron
United States of America
;
_audit_update_record             
;
2024-02-01 deposited with the CCDC.	2024-05-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H17 Cu N9'
_chemical_formula_weight         615.10

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+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                   10.247(13)
_cell_length_b                   33.06(5)
_cell_length_c                   9.773(12)
_cell_angle_alpha                90
_cell_angle_beta                 104.16(6)
_cell_angle_gamma                90
_cell_volume                     3210(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2544
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      28.13

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_F_000             1252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.096
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.066
_exptl_absorpt_coefficient_mu    0.718
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5167
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26202
_diffrn_reflns_av_unetI/netI     0.1047
_diffrn_reflns_av_R_equivalents  0.1628
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.232
_diffrn_reflns_theta_max         25.193
_diffrn_reflns_theta_full        25.193
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2899
_reflns_number_gt                2098
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
Disordered DMF solvent was squeezed out with PLATON.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0950P)²+5.5399P] 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         2899
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.0712
_refine_ls_wR_factor_ref         0.1860
_refine_ls_wR_factor_gt          0.1717
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5905(5) 0.59158(15) 0.6271(5) 0.0261(11) Uani 1 1 d . . . . .
C2 C 0.6724(6) 0.57274(15) 0.7475(5) 0.0333(13) Uani 1 1 d . . . . .
H2 H 0.687743 0.584895 0.838107 0.040 Uiso 1 1 calc R U . . .
C3 C 0.7304(7) 0.53528(18) 0.7281(6) 0.0510(18) Uani 1 1 d . . . . .
H3 H 0.788139 0.522347 0.806856 0.061 Uiso 1 1 calc R U . . .
C4 C 0.7048(10) 0.5162(2) 0.5932(6) 0.075(3) Uani 1 1 d . . . . .
H4 H 0.744584 0.490666 0.584047 0.091 Uiso 1 1 calc R U . . .
C5 C 0.6215(9) 0.53463(17) 0.4735(6) 0.060(2) Uani 1 1 d . . . . .
H5 H 0.602448 0.521688 0.384032 0.072 Uiso 1 1 calc R U . . .
C6 C 0.5673(6) 0.57288(16) 0.4906(5) 0.0360(14) Uani 1 1 d . . . . .
C7 C 0.4648(5) 0.63209(14) 0.4657(5) 0.0212(11) Uani 1 1 d . . . . .
C8 C 0.3973(4) 0.66794(15) 0.3936(5) 0.0245(11) Uani 1 1 d . . . . .
C9 C 0.3258(5) 0.66334(16) 0.2446(5) 0.0297(12) Uani 1 1 d . . . . .
C10 C 0.4042(4) 0.70634(15) 0.4540(5) 0.0226(11) Uani 1 1 d . . . . .
C11 C 0.3718(5) 0.74610(16) 0.3827(5) 0.0268(12) Uani 1 1 d . . . . .
C12 C 0.3205(5) 0.75843(18) 0.2403(5) 0.0318(13) Uani 1 1 d . . . . .
H12 H 0.292994 0.739066 0.167026 0.038 Uiso 1 1 calc R U . . .
C13 C 0.3115(5) 0.80078(19) 0.2105(6) 0.0377(14) Uani 1 1 d . . . . .
H13 H 0.278039 0.809721 0.116070 0.045 Uiso 1 1 calc R U . . .
C14 C 0.3511(5) 0.82912(18) 0.3178(6) 0.0385(15) Uani 1 1 d . . . . .
H14 H 0.344903 0.857060 0.294332 0.046 Uiso 1 1 calc R U . . .
C15 C 0.4001(5) 0.81775(16) 0.4606(6) 0.0299(12) Uani 1 1 d . . . . .
H15 H 0.425571 0.837432 0.533051 0.036 Uiso 1 1 calc R U . . .
C16 C 0.4098(5) 0.77565(16) 0.4914(5) 0.0274(12) Uani 1 1 d . . . . .
C17 C 0.4596(4) 0.75374(15) 0.6260(5) 0.0222(11) Uani 1 1 d . . . . .
Cu1 Cu 0.500000 0.67015(2) 0.750000 0.0197(3) Uani 1 2 d S T P . .
N1 N 0.5224(4) 0.62957(12) 0.6085(4) 0.0213(9) Uani 1 1 d . . . . .
N2 N 0.4576(4) 0.71280(12) 0.6019(4) 0.0224(9) Uani 1 1 d . . . . .
N3 N 0.500000 0.77397(17) 0.750000 0.0254(13) Uani 1 2 d S T P . .
N4 N 0.4853(5) 0.59873(13) 0.3910(4) 0.0337(11) Uani 1 1 d . . . . .
H4A H 0.453960 0.594341 0.300102 0.040 Uiso 0.5 1 calc R U P . .
N5 N 0.2669(5) 0.65880(15) 0.1275(5) 0.0375(12) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.412(7) . ?
C1 N1 1.426(6) . ?
C1 C6 1.436(7) . ?
C2 C3 1.406(8) . ?
C3 C4 1.427(8) . ?
C4 C5 1.407(9) . ?
C5 C6 1.407(8) . ?
C6 N4 1.408(7) . ?
C7 N4 1.366(6) . ?
C7 N1 1.379(6) . ?
C7 C8 1.463(7) . ?
C8 C10 1.394(7) . ?
C8 C9 1.469(7) . ?
C9 N5 1.166(6) . ?
C10 N2 1.431(6) . ?
C10 C11 1.487(7) . ?
C11 C12 1.422(7) . ?
C11 C16 1.426(7) . ?
C12 C13 1.428(8) . ?
C13 C14 1.390(8) . ?
C14 C15 1.414(8) . ?
C15 C16 1.422(7) . ?
C16 C17 1.478(7) . ?
C17 N3 1.357(6) . ?
C17 N2 1.373(6) . ?
Cu1 N1 1.980(4) 2_656 ?
Cu1 N1 1.980(4) . ?
Cu1 N2 1.991(4) 2_656 ?
Cu1 N2 1.991(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
C2 C1 N1 131.8(4) . . ?
C2 C1 C6 120.9(5) . . ?
N1 C1 C6 107.2(4) . . ?
C3 C2 C1 117.4(5) . . ?
C2 C3 C4 121.7(5) . . ?
C5 C4 C3 120.8(6) . . ?
C6 C5 C4 117.9(5) . . ?
N4 C6 C5 130.5(5) . . ?
N4 C6 C1 108.4(5) . . ?
C5 C6 C1 121.1(5) . . ?
N4 C7 N1 114.1(4) . . ?
N4 C7 C8 120.8(4) . . ?
N1 C7 C8 124.9(4) . . ?
C10 C8 C7 124.4(4) . . ?
C10 C8 C9 118.4(4) . . ?
C7 C8 C9 117.1(4) . . ?
N5 C9 C8 178.0(6) . . ?
C8 C10 N2 122.1(4) . . ?
C8 C10 C11 128.6(5) . . ?
N2 C10 C11 109.2(4) . . ?
C12 C11 C16 120.1(5) . . ?
C12 C11 C10 134.4(5) . . ?
C16 C11 C10 105.5(4) . . ?
C11 C12 C13 118.0(5) . . ?
C14 C13 C12 121.0(5) . . ?
C13 C14 C15 122.2(5) . . ?
C14 C15 C16 117.3(5) . . ?
C15 C16 C11 121.3(5) . . ?
C15 C16 C17 131.2(5) . . ?
C11 C16 C17 107.4(4) . . ?
N3 C17 N2 128.8(5) . . ?
N3 C17 C16 121.1(5) . . ?
N2 C17 C16 110.1(4) . . ?
N1 Cu1 N1 94.7(2) 2_656 . ?
N1 Cu1 N2 90.81(19) 2_656 2_656 ?
N1 Cu1 N2 161.01(15) . 2_656 ?
N1 Cu1 N2 161.01(15) 2_656 . ?
N1 Cu1 N2 90.82(19) . . ?
N2 Cu1 N2 89.8(3) 2_656 . ?
C7 N1 C1 104.9(4) . . ?
C7 N1 Cu1 124.9(3) . . ?
C1 N1 Cu1 130.1(3) . . ?
C17 N2 C10 107.8(4) . . ?
C17 N2 Cu1 125.6(3) . . ?
C10 N2 Cu1 126.2(3) . . ?
C17 N3 C17 121.0(6) . 2_656 ?
C7 N4 C6 105.3(4) . . ?

_refine_diff_density_max         0.401
_refine_diff_density_min         -0.679
_refine_diff_density_rms         0.116
# SQUEEZE RESULTS (Version = 300517)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
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 0.500 0.000 -0.013 369 123 ' '
2 1.000 0.500 -0.031 369 123 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?




####################################################################### 
# 
# 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_NiHlp
_database_code_depnum_ccdc_archive 'CCDC 2330322'
loop_
_audit_author_name
_audit_author_address
'Christopher Ziegler'
;University of Akron
United States of America
;
_audit_update_record             
;
2024-02-01 deposited with the CCDC.	2024-05-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H24 N10 Ni O'
_chemical_formula_weight         683.37

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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   9.2915(12)
_cell_length_b                   32.458(4)
_cell_length_c                   10.0812(12)
_cell_angle_alpha                90
_cell_angle_beta                 100.874(5)
_cell_angle_gamma                90
_cell_volume                     2985.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6598
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      28.28

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.102
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.056
_exptl_absorpt_coefficient_mu    0.702
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6683
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            65544
_diffrn_reflns_av_unetI/netI     0.0987
_diffrn_reflns_av_R_equivalents  0.1980
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.151
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5245
_reflns_number_gt                3603
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0482P)²+5.5706P] 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         5245
_refine_ls_number_parameters     444
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.1447
_refine_ls_wR_factor_gt          0.1278
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
C1 C 0.8762(5) 0.59445(13) 0.4446(4) 0.0144(10) Uani 1 1 d . . . . .
C2 C 0.7540(5) 0.58064(13) 0.3525(4) 0.0164(10) Uani 1 1 d . . . . .
H2 H 0.663263 0.594963 0.340164 0.020 Uiso 1 1 calc R U . . .
C3 C 0.7701(5) 0.54565(14) 0.2809(5) 0.0223(11) Uani 1 1 d . . . . .
H3 H 0.689012 0.535857 0.216865 0.027 Uiso 1 1 calc R U . . .
C4 C 0.9032(5) 0.52372(15) 0.2991(5) 0.0279(12) Uani 1 1 d . . . . .
H4 H 0.909642 0.499371 0.248310 0.033 Uiso 1 1 calc R U . . .
C5 C 1.0229(5) 0.53700(15) 0.3889(5) 0.0245(11) Uani 1 1 d . . . . .
H5 H 1.112936 0.522324 0.401092 0.029 Uiso 1 1 calc R U . . .
C6 C 1.0092(5) 0.57263(13) 0.4618(5) 0.0166(10) Uani 1 1 d . . . . .
C7 C 1.0428(5) 0.62644(13) 0.5884(4) 0.0149(10) Uani 1 1 d . . . . .
C8 C 1.1185(5) 0.66037(13) 0.6633(4) 0.0159(10) Uani 1 1 d . . . . .
C9 C 1.2629(5) 0.65226(14) 0.7379(5) 0.0197(11) Uani 1 1 d . . . . .
C10 C 1.0645(5) 0.69960(14) 0.6560(4) 0.0147(10) Uani 1 1 d . . . . .
C11 C 1.1433(5) 0.73791(14) 0.6943(4) 0.0177(10) Uani 1 1 d . . . . .
C12 C 1.2898(5) 0.74694(14) 0.7464(4) 0.0195(10) Uani 1 1 d . . . . .
H12 H 1.359418 0.725687 0.773608 0.023 Uiso 1 1 calc R U . . .
C13 C 1.3298(5) 0.78798(15) 0.7569(5) 0.0238(11) Uani 1 1 d . . . . .
H13 H 1.429011 0.795023 0.791271 0.029 Uiso 1 1 calc R U . . .
C14 C 1.2280(5) 0.81922(15) 0.7182(5) 0.0237(12) Uani 1 1 d . . . . .
H14 H 1.259768 0.847089 0.725915 0.028 Uiso 1 1 calc R U . . .
C15 C 1.0808(5) 0.81072(15) 0.6685(4) 0.0207(11) Uani 1 1 d . . . . .
H15 H 1.010800 0.832021 0.643613 0.025 Uiso 1 1 calc R U . . .
C16 C 1.0424(5) 0.76969(14) 0.6576(4) 0.0172(10) Uani 1 1 d . . . . .
C17 C 0.9013(5) 0.75006(14) 0.6046(4) 0.0159(10) Uani 1 1 d . . . . .
C18 C 0.6529(5) 0.75365(13) 0.5305(4) 0.0154(10) Uani 1 1 d . . . . .
C19 C 0.5199(5) 0.77690(13) 0.4809(4) 0.0145(10) Uani 1 1 d . . . . .
C20 C 0.4959(5) 0.81905(14) 0.4708(5) 0.0217(11) Uani 1 1 d . . . . .
H20 H 0.573457 0.838139 0.497620 0.026 Uiso 1 1 calc R U . . .
C21 C 0.3547(5) 0.83218(15) 0.4202(5) 0.0218(11) Uani 1 1 d . . . . .
H21 H 0.334685 0.860870 0.412345 0.026 Uiso 1 1 calc R U . . .
C22 C 0.2413(5) 0.80426(14) 0.3807(4) 0.0199(11) Uani 1 1 d . . . . .
H22 H 0.145524 0.814253 0.346043 0.024 Uiso 1 1 calc R U . . .
C23 C 0.2654(5) 0.76179(14) 0.3910(5) 0.0198(11) Uani 1 1 d . . . . .
H23 H 0.187613 0.742733 0.364863 0.024 Uiso 1 1 calc R U . . .
C24 C 0.4076(5) 0.74848(13) 0.4409(4) 0.0156(10) Uani 1 1 d . . . . .
C25 C 0.4749(5) 0.70765(13) 0.4722(4) 0.0140(10) Uani 1 1 d . . . . .
C26 C 0.4085(4) 0.67017(13) 0.4539(4) 0.0151(9) Uani 1 1 d . . . . .
C27 C 0.2609(5) 0.66620(13) 0.3826(4) 0.0157(10) Uani 1 1 d . . . . .
C28 C 0.4784(5) 0.63287(13) 0.5116(4) 0.0145(10) Uani 1 1 d . . . . .
C29 C 0.5023(5) 0.57106(13) 0.5996(4) 0.0170(10) Uani 1 1 d . . . . .
C30 C 0.4804(5) 0.53149(14) 0.6441(5) 0.0224(11) Uani 1 1 d . . . . .
H30 H 0.387405 0.518416 0.622687 0.027 Uiso 1 1 calc R U . . .
C31 C 0.5992(5) 0.51205(14) 0.7205(5) 0.0234(11) Uani 1 1 d . . . . .
H31 H 0.589028 0.484879 0.752526 0.028 Uiso 1 1 calc R U . . .
C32 C 0.7358(5) 0.53208(14) 0.7518(5) 0.0219(11) Uani 1 1 d . . . . .
H32 H 0.815482 0.518229 0.806681 0.026 Uiso 1 1 calc R U . . .
C33 C 0.7579(5) 0.57112(13) 0.7054(4) 0.0173(10) Uani 1 1 d . . . . .
H33 H 0.851134 0.584060 0.726136 0.021 Uiso 1 1 calc R U . . .
C34 C 0.6387(5) 0.59071(13) 0.6275(4) 0.0148(10) Uani 1 1 d . . . . .
C35 C 0.2868(7) 0.59189(17) 0.1469(6) 0.0426(15) Uani 1 1 d . . . . .
H35 H 0.210541 0.603010 0.186905 0.051 Uiso 1 1 calc R U . . .
C36 C 0.0897(7) 0.5606(2) -0.0118(8) 0.072(2) Uani 1 1 d . . . . .
H36A H 0.031110 0.572803 0.049267 0.107 Uiso 1 1 calc R U . . .
H36B H 0.075878 0.530618 -0.014437 0.107 Uiso 1 1 calc R U . . .
H36C H 0.058319 0.571905 -0.102797 0.107 Uiso 1 1 calc R U . . .
C37 C 0.3473(8) 0.5538(2) -0.0413(7) 0.063(2) Uani 1 1 d . . . . .
H37A H 0.442545 0.567347 -0.014645 0.094 Uiso 1 1 calc R U . . .
H37B H 0.309566 0.558691 -0.137447 0.094 Uiso 1 1 calc R U . . .
H37C H 0.358719 0.524057 -0.025043 0.094 Uiso 1 1 calc R U . . .
N1 N 0.8999(4) 0.62888(11) 0.5287(4) 0.0142(8) Uani 1 1 d . . . . .
N2 N 0.9177(4) 0.70866(11) 0.5989(4) 0.0152(8) Uani 1 1 d . . . . .
N3 N 0.7810(4) 0.77225(11) 0.5688(4) 0.0166(8) Uani 1 1 d . . . . .
N4 N 0.6238(4) 0.71267(11) 0.5279(4) 0.0154(8) Uani 1 1 d . . . . .
N5 N 0.6212(4) 0.62994(11) 0.5661(4) 0.0142(8) Uani 1 1 d . . . . .
N6 N 1.1134(4) 0.59323(11) 0.5552(4) 0.0185(9) Uani 1 1 d . . . . .
N7 N 0.4044(4) 0.59824(11) 0.5262(4) 0.0159(8) Uani 1 1 d . . . . .
H7 H 0.310735 0.593717 0.494867 0.019 Uiso 1 1 calc R U . . .
N8 N 1.3781(4) 0.64603(13) 0.7999(4) 0.0282(10) Uani 1 1 d . . . . .
N9 N 0.1432(4) 0.66110(11) 0.3240(4) 0.0223(9) Uani 1 1 d . . . . .
N10 N 0.2461(5) 0.57013(14) 0.0370(4) 0.0382(12) Uani 1 1 d . . . . .
Ni1 Ni 0.76536(6) 0.66997(2) 0.55611(6) 0.01286(17) Uani 1 1 d . . . . .
O1 O 0.4108(5) 0.59943(13) 0.2033(5) 0.0576(12) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.395(5) . ?
C1 C2 1.398(6) . ?
C1 C6 1.407(6) . ?
C2 C3 1.369(6) . ?
C3 C4 1.408(6) . ?
C4 C5 1.365(7) . ?
C5 C6 1.389(6) . ?
C6 N6 1.388(6) . ?
C7 N6 1.337(5) . ?
C7 N1 1.353(5) . ?
C7 C8 1.441(6) . ?
C8 C10 1.366(6) . ?
C8 C9 1.433(6) . ?
C9 N8 1.152(6) . ?
C10 N2 1.407(5) . ?
C10 C11 1.458(6) . ?
C11 C12 1.395(6) . ?
C11 C16 1.396(6) . ?
C12 C13 1.382(6) . ?
C13 C14 1.391(7) . ?
C14 C15 1.393(6) . ?
C15 C16 1.378(6) . ?
C16 C17 1.465(6) . ?
C17 N3 1.321(6) . ?
C17 N2 1.355(5) . ?
C18 N3 1.326(5) . ?
C18 N4 1.356(5) . ?
C18 C19 1.454(6) . ?
C19 C20 1.387(6) . ?
C19 C24 1.394(6) . ?
C20 C21 1.383(6) . ?
C21 C22 1.389(7) . ?
C22 C23 1.397(6) . ?
C23 C24 1.391(6) . ?
C24 C25 1.474(6) . ?
C25 C26 1.361(6) . ?
C25 N4 1.401(5) . ?
C26 C27 1.429(6) . ?
C26 C28 1.444(6) . ?
C27 N9 1.153(5) . ?
C28 N7 1.341(5) . ?
C28 N5 1.340(5) . ?
C29 N7 1.378(5) . ?
C29 C30 1.388(6) . ?
C29 C34 1.400(6) . ?
C30 C31 1.374(6) . ?
C31 C32 1.408(6) . ?
C32 C33 1.379(6) . ?
C33 C34 1.385(6) . ?
C34 N5 1.412(5) . ?
C35 O1 1.210(6) . ?
C35 N10 1.308(7) . ?
C36 N10 1.477(8) . ?
C37 N10 1.439(7) . ?
N1 Ni1 1.884(3) . ?
N2 Ni1 1.881(3) . ?
N4 Ni1 1.895(4) . ?
N5 Ni1 1.883(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
N1 C1 C2 132.5(4) . . ?
N1 C1 C6 107.1(4) . . ?
C2 C1 C6 120.3(4) . . ?
C3 C2 C1 117.4(4) . . ?
C2 C3 C4 122.1(4) . . ?
C5 C4 C3 120.9(4) . . ?
C4 C5 C6 118.0(4) . . ?
C5 C6 N6 129.6(4) . . ?
C5 C6 C1 121.4(4) . . ?
N6 C6 C1 109.0(4) . . ?
N6 C7 N1 115.0(4) . . ?
N6 C7 C8 122.2(4) . . ?
N1 C7 C8 122.0(4) . . ?
C10 C8 C9 119.9(4) . . ?
C10 C8 C7 123.1(4) . . ?
C9 C8 C7 116.8(4) . . ?
N8 C9 C8 178.8(5) . . ?
C8 C10 N2 122.3(4) . . ?
C8 C10 C11 128.3(4) . . ?
N2 C10 C11 109.3(4) . . ?
C12 C11 C16 120.2(4) . . ?
C12 C11 C10 133.2(4) . . ?
C16 C11 C10 106.3(4) . . ?
C13 C12 C11 117.4(4) . . ?
C12 C13 C14 121.5(5) . . ?
C13 C14 C15 121.7(4) . . ?
C16 C15 C14 116.3(5) . . ?
C15 C16 C11 122.8(4) . . ?
C15 C16 C17 130.6(4) . . ?
C11 C16 C17 106.6(4) . . ?
N3 C17 N2 128.7(4) . . ?
N3 C17 C16 121.0(4) . . ?
N2 C17 C16 110.3(4) . . ?
N3 C18 N4 128.1(4) . . ?
N3 C18 C19 121.5(4) . . ?
N4 C18 C19 110.4(4) . . ?
C20 C19 C24 122.0(4) . . ?
C20 C19 C18 130.7(4) . . ?
C24 C19 C18 107.3(4) . . ?
C21 C20 C19 117.3(4) . . ?
C20 C21 C22 121.3(4) . . ?
C21 C22 C23 121.3(4) . . ?
C24 C23 C22 117.5(4) . . ?
C23 C24 C19 120.5(4) . . ?
C23 C24 C25 133.8(4) . . ?
C19 C24 C25 105.6(4) . . ?
C26 C25 N4 123.1(4) . . ?
C26 C25 C24 127.7(4) . . ?
N4 C25 C24 109.2(4) . . ?
C25 C26 C27 121.1(4) . . ?
C25 C26 C28 122.5(4) . . ?
C27 C26 C28 116.3(4) . . ?
N9 C27 C26 176.8(5) . . ?
N7 C28 N5 112.6(4) . . ?
N7 C28 C26 123.1(4) . . ?
N5 C28 C26 124.1(4) . . ?
N7 C29 C30 130.1(4) . . ?
N7 C29 C34 107.3(4) . . ?
C30 C29 C34 122.6(4) . . ?
C31 C30 C29 117.0(4) . . ?
C30 C31 C32 120.6(4) . . ?
C33 C32 C31 122.3(4) . . ?
C32 C33 C34 117.4(4) . . ?
C33 C34 C29 120.1(4) . . ?
C33 C34 N5 132.6(4) . . ?
C29 C34 N5 107.3(4) . . ?
O1 C35 N10 127.2(6) . . ?
C7 N1 C1 104.6(3) . . ?
C7 N1 Ni1 126.8(3) . . ?
C1 N1 Ni1 128.5(3) . . ?
C17 N2 C10 107.3(3) . . ?
C17 N2 Ni1 125.9(3) . . ?
C10 N2 Ni1 125.7(3) . . ?
C17 N3 C18 119.9(4) . . ?
C18 N4 C25 107.4(4) . . ?
C18 N4 Ni1 125.7(3) . . ?
C25 N4 Ni1 125.5(3) . . ?
C28 N5 C34 105.5(3) . . ?
C28 N5 Ni1 126.0(3) . . ?
C34 N5 Ni1 128.4(3) . . ?
C7 N6 C6 104.3(4) . . ?
C28 N7 C29 107.2(4) . . ?
C35 N10 C37 123.3(6) . . ?
C35 N10 C36 120.4(5) . . ?
C37 N10 C36 116.3(5) . . ?
N2 Ni1 N5 163.96(16) . . ?
N2 Ni1 N1 90.85(15) . . ?
N5 Ni1 N1 91.02(14) . . ?
N2 Ni1 N4 90.98(15) . . ?
N5 Ni1 N4 91.83(15) . . ?
N1 Ni1 N4 163.14(15) . . ?

_refine_diff_density_max         0.831
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.090



####################################################################### 
# 
# 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_CoHlpDMF
_database_code_depnum_ccdc_archive 'CCDC 2330323'
loop_
_audit_author_name
_audit_author_address
'Christopher Ziegler'
;University of Akron
United States of America
;
_audit_update_record             
;
2024-02-01 deposited with the CCDC.	2024-05-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H24 Co N10 O'
_chemical_formula_weight         683.59

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'
Co Co 0.3494 0.9721 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   9.544(8)
_cell_length_b                   12.116(10)
_cell_length_c                   14.974(14)
_cell_angle_alpha                93.98(6)
_cell_angle_beta                 99.20(8)
_cell_angle_gamma                104.84(3)
_cell_volume                     1641(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5582
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      26.83

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             702
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.122
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.075
_exptl_absorpt_coefficient_mu    0.570
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5890
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            55759
_diffrn_reflns_av_unetI/netI     0.1038
_diffrn_reflns_av_R_equivalents  0.1603
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.387
_diffrn_reflns_theta_max         25.199
_diffrn_reflns_theta_full        25.199
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5922
_reflns_number_gt                4505
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
Disordered DMF solvent was squeezed out by PLATON
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0603P)²+1.1860P] 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         5922
_refine_ls_number_parameters     444
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.1592
_refine_ls_wR_factor_gt          0.1468
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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
C1 C 0.6359(4) 0.1098(3) 0.7611(3) 0.0180(9) Uani 1 1 d . . . . .
C2 C 0.5226(5) 0.0439(4) 0.8000(3) 0.0242(10) Uani 1 1 d . . . . .
H2 H 0.446428 0.074402 0.815930 0.029 Uiso 1 1 calc R U . . .
C3 C 0.5259(5) -0.0663(4) 0.8141(3) 0.0260(10) Uani 1 1 d . . . . .
H3 H 0.450807 -0.111801 0.841139 0.031 Uiso 1 1 calc R U . . .
C4 C 0.6359(5) -0.1146(4) 0.7903(3) 0.0281(10) Uani 1 1 d . . . . .
H4 H 0.634078 -0.191054 0.801554 0.034 Uiso 1 1 calc R U . . .
C5 C 0.7472(5) -0.0510(4) 0.7502(3) 0.0269(10) Uani 1 1 d . . . . .
H5 H 0.821350 -0.082743 0.732828 0.032 Uiso 1 1 calc R U . . .
C6 C 0.7455(4) 0.0619(3) 0.7366(3) 0.0204(9) Uani 1 1 d . . . . .
C7 C 0.7945(4) 0.2385(3) 0.7074(3) 0.0178(9) Uani 1 1 d . . . . .
C8 C 0.8813(4) 0.3488(3) 0.6896(3) 0.0195(9) Uani 1 1 d . . . . .
C9 C 0.9934(5) 0.3462(3) 0.6355(3) 0.0253(10) Uani 1 1 d . . . . .
C10 C 0.8709(4) 0.4508(3) 0.7282(3) 0.0211(9) Uani 1 1 d . . . . .
C11 C 0.9725(4) 0.5648(3) 0.7340(3) 0.0217(9) Uani 1 1 d . . . . .
C12 C 1.1008(5) 0.6097(4) 0.6989(3) 0.0336(11) Uani 1 1 d . . . . .
H12 H 1.138902 0.561502 0.662354 0.040 Uiso 1 1 calc R U . . .
C13 C 1.1699(5) 0.7257(4) 0.7191(4) 0.0390(12) Uani 1 1 d . . . . .
H13 H 1.255360 0.757783 0.694676 0.047 Uiso 1 1 calc R U . . .
C14 C 1.1171(5) 0.7969(4) 0.7743(4) 0.0395(12) Uani 1 1 d . . . . .
H14 H 1.167729 0.876213 0.787685 0.047 Uiso 1 1 calc R U . . .
C15 C 0.9914(5) 0.7532(4) 0.8101(3) 0.0324(11) Uani 1 1 d . . . . .
H15 H 0.955543 0.801091 0.848493 0.039 Uiso 1 1 calc R U . . .
C16 C 0.9203(4) 0.6379(4) 0.7879(3) 0.0251(10) Uani 1 1 d . . . . .
C17 C 0.7840(4) 0.5689(3) 0.8107(3) 0.0216(9) Uani 1 1 d . . . . .
C18 C 0.5672(5) 0.5566(3) 0.8627(3) 0.0214(9) Uani 1 1 d . . . . .
C19 C 0.4799(4) 0.6053(3) 0.9189(3) 0.0206(9) Uani 1 1 d . . . . .
C20 C 0.5131(5) 0.7113(4) 0.9700(3) 0.0268(10) Uani 1 1 d . . . . .
H20 H 0.606024 0.765938 0.974621 0.032 Uiso 1 1 calc R U . . .
C21 C 0.4042(5) 0.7346(4) 1.0145(3) 0.0338(11) Uani 1 1 d . . . . .
H21 H 0.421971 0.807121 1.049150 0.041 Uiso 1 1 calc R U . . .
C22 C 0.2699(5) 0.6527(4) 1.0087(3) 0.0326(11) Uani 1 1 d . . . . .
H22 H 0.198430 0.670011 1.040681 0.039 Uiso 1 1 calc R U . . .
C23 C 0.2379(5) 0.5471(4) 0.9577(3) 0.0277(10) Uani 1 1 d . . . . .
H23 H 0.145420 0.492231 0.953922 0.033 Uiso 1 1 calc R U . . .
C24 C 0.3450(5) 0.5226(3) 0.9117(3) 0.0217(9) Uani 1 1 d . . . . .
C25 C 0.3531(4) 0.4257(3) 0.8504(3) 0.0196(9) Uani 1 1 d . . . . .
C26 C 0.2483(4) 0.3237(4) 0.8244(3) 0.0218(9) Uani 1 1 d . . . . .
C27 C 0.1162(5) 0.3030(4) 0.8629(3) 0.0230(9) Uani 1 1 d . . . . .
C28 C 0.2576(4) 0.2349(4) 0.7583(3) 0.0232(9) Uani 1 1 d . . . . .
C29 C 0.1851(4) 0.0862(4) 0.6551(3) 0.0260(10) Uani 1 1 d . . . . .
C30 C 0.1077(5) -0.0121(4) 0.5960(3) 0.0361(12) Uani 1 1 d . . . . .
H30 H 0.008917 -0.051162 0.598997 0.043 Uiso 1 1 calc R U . . .
C31 C 0.1807(5) -0.0502(4) 0.5333(3) 0.0340(11) Uani 1 1 d . . . . .
H31 H 0.132081 -0.117906 0.492763 0.041 Uiso 1 1 calc R U . . .
C32 C 0.3255(5) 0.0093(4) 0.5281(3) 0.0317(11) Uani 1 1 d . . . . .
H32 H 0.371349 -0.017236 0.482283 0.038 Uiso 1 1 calc R U . . .
C33 C 0.4024(5) 0.1046(4) 0.5871(3) 0.0238(10) Uani 1 1 d . . . . .
H33 H 0.500684 0.143846 0.583203 0.029 Uiso 1 1 calc R U . . .
C34 C 0.3318(4) 0.1427(3) 0.6537(3) 0.0195(9) Uani 1 1 d . . . . .
C35 C 0.4452(5) 0.3680(3) 0.5597(3) 0.0229(9) Uani 1 1 d . . . . .
H35 H 0.358795 0.370640 0.582712 0.027 Uiso 1 1 calc R U . . .
C36 C 0.2936(5) 0.3346(4) 0.4099(3) 0.0368(12) Uani 1 1 d . . . . .
H36A H 0.264112 0.257692 0.376042 0.055 Uiso 1 1 calc R U . . .
H36B H 0.303627 0.392566 0.367128 0.055 Uiso 1 1 calc R U . . .
H36C H 0.218368 0.342621 0.445593 0.055 Uiso 1 1 calc R U . . .
C37 C 0.5586(6) 0.3400(5) 0.4295(3) 0.0423(13) Uani 1 1 d . . . . .
H37A H 0.648123 0.359997 0.476387 0.064 Uiso 1 1 calc R U . . .
H37B H 0.571513 0.392096 0.382348 0.064 Uiso 1 1 calc R U . . .
H37C H 0.540319 0.260666 0.401995 0.064 Uiso 1 1 calc R U . . .
Co1 Co 0.57002(6) 0.34362(5) 0.75746(4) 0.01798(18) Uani 1 1 d . . . . .
N1 N 0.6682(3) 0.2236(3) 0.7403(2) 0.0182(7) Uani 1 1 d . . . . .
N2 N 0.7563(4) 0.4572(3) 0.7757(2) 0.0206(8) Uani 1 1 d . . . . .
N3 N 0.7011(4) 0.6160(3) 0.8559(2) 0.0227(8) Uani 1 1 d . . . . .
N4 N 0.4890(4) 0.4503(3) 0.8211(2) 0.0202(8) Uani 1 1 d . . . . .
N5 N 0.3785(3) 0.2357(3) 0.7225(2) 0.0202(8) Uani 1 1 d . . . . .
N6 N 0.8449(4) 0.1441(3) 0.7010(2) 0.0208(8) Uani 1 1 d . . . . .
N7 N 0.1401(4) 0.1466(3) 0.7218(2) 0.0293(9) Uani 1 1 d . . . . .
H7 H 0.052549 0.130550 0.737145 0.035 Uiso 1 1 calc R U . . .
N8 N 1.0802(4) 0.3452(3) 0.5911(3) 0.0333(9) Uani 1 1 d . . . . .
N9 N 0.0101(4) 0.2878(3) 0.8921(3) 0.0343(10) Uani 1 1 d . . . . .
N10 N 0.4334(4) 0.3510(3) 0.4706(2) 0.0263(8) Uani 1 1 d . . . . .
O1 O 0.5594(3) 0.3807(2) 0.61513(19) 0.0252(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
C1 N1 1.402(5) . ?
C1 C2 1.404(6) . ?
C1 C6 1.404(5) . ?
C2 C3 1.374(6) . ?
C3 C4 1.406(6) . ?
C4 C5 1.389(6) . ?
C5 C6 1.400(6) . ?
C6 N6 1.389(5) . ?
C7 N1 1.349(5) . ?
C7 N6 1.353(5) . ?
C7 C8 1.448(5) . ?
C8 C10 1.360(6) . ?
C8 C9 1.447(6) . ?
C9 N8 1.144(5) . ?
C10 N2 1.412(5) . ?
C10 C11 1.459(6) . ?
C11 C16 1.392(6) . ?
C11 C12 1.405(6) . ?
C12 C13 1.380(6) . ?
C13 C14 1.392(7) . ?
C14 C15 1.388(6) . ?
C15 C16 1.378(6) . ?
C16 C17 1.461(6) . ?
C17 N3 1.326(5) . ?
C17 N2 1.360(5) . ?
C18 N3 1.321(5) . ?
C18 N4 1.360(5) . ?
C18 C19 1.470(6) . ?
C19 C20 1.383(6) . ?
C19 C24 1.397(6) . ?
C20 C21 1.397(6) . ?
C21 C22 1.390(6) . ?
C22 C23 1.380(6) . ?
C23 C24 1.400(6) . ?
C24 C25 1.465(6) . ?
C25 C26 1.362(6) . ?
C25 N4 1.402(5) . ?
C26 C27 1.441(6) . ?
C26 C28 1.440(6) . ?
C27 N9 1.144(5) . ?
C28 N7 1.345(5) . ?
C28 N5 1.345(5) . ?
C29 N7 1.384(5) . ?
C29 C30 1.393(6) . ?
C29 C34 1.396(6) . ?
C30 C31 1.377(6) . ?
C31 C32 1.403(6) . ?
C32 C33 1.367(6) . ?
C33 C34 1.404(6) . ?
C34 N5 1.402(5) . ?
C35 O1 1.229(5) . ?
C35 N10 1.317(5) . ?
C36 N10 1.449(6) . ?
C37 N10 1.460(6) . ?
Co1 N2 1.916(4) . ?
Co1 N5 1.923(4) . ?
Co1 N4 1.937(4) . ?
Co1 N1 1.945(3) . ?
Co1 O1 2.201(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
N1 C1 C2 132.4(4) . . ?
N1 C1 C6 107.6(3) . . ?
C2 C1 C6 120.0(4) . . ?
C3 C2 C1 117.5(4) . . ?
C2 C3 C4 122.7(4) . . ?
C5 C4 C3 120.3(4) . . ?
C4 C5 C6 117.3(4) . . ?
N6 C6 C5 129.0(4) . . ?
N6 C6 C1 108.9(4) . . ?
C5 C6 C1 122.1(4) . . ?
N1 C7 N6 115.0(3) . . ?
N1 C7 C8 123.8(3) . . ?
N6 C7 C8 120.9(3) . . ?
C10 C8 C9 120.3(4) . . ?
C10 C8 C7 123.1(4) . . ?
C9 C8 C7 116.3(3) . . ?
N8 C9 C8 178.3(5) . . ?
C8 C10 N2 121.8(4) . . ?
C8 C10 C11 128.6(4) . . ?
N2 C10 C11 109.5(3) . . ?
C16 C11 C12 119.3(4) . . ?
C16 C11 C10 106.2(4) . . ?
C12 C11 C10 134.5(4) . . ?
C13 C12 C11 118.2(4) . . ?
C12 C13 C14 121.5(4) . . ?
C15 C14 C13 120.8(4) . . ?
C16 C15 C14 117.6(4) . . ?
C15 C16 C11 122.5(4) . . ?
C15 C16 C17 130.5(4) . . ?
C11 C16 C17 107.0(4) . . ?
N3 C17 N2 127.9(4) . . ?
N3 C17 C16 121.6(4) . . ?
N2 C17 C16 110.5(4) . . ?
N3 C18 N4 128.6(4) . . ?
N3 C18 C19 120.6(4) . . ?
N4 C18 C19 110.7(4) . . ?
C20 C19 C24 122.8(4) . . ?
C20 C19 C18 130.4(4) . . ?
C24 C19 C18 106.7(3) . . ?
C19 C20 C21 117.1(4) . . ?
C22 C21 C20 120.7(4) . . ?
C23 C22 C21 121.7(4) . . ?
C22 C23 C24 118.4(4) . . ?
C19 C24 C23 119.2(4) . . ?
C19 C24 C25 105.6(3) . . ?
C23 C24 C25 135.2(4) . . ?
C26 C25 N4 122.5(4) . . ?
C26 C25 C24 127.1(4) . . ?
N4 C25 C24 110.4(3) . . ?
C25 C26 C27 118.6(4) . . ?
C25 C26 C28 124.5(4) . . ?
C27 C26 C28 116.8(4) . . ?
N9 C27 C26 178.5(5) . . ?
N7 C28 N5 113.7(4) . . ?
N7 C28 C26 121.9(4) . . ?
N5 C28 C26 124.3(4) . . ?
N7 C29 C30 130.2(4) . . ?
N7 C29 C34 107.4(4) . . ?
C30 C29 C34 122.3(4) . . ?
C31 C30 C29 117.1(4) . . ?
C30 C31 C32 121.1(4) . . ?
C33 C32 C31 121.7(4) . . ?
C32 C33 C34 118.0(4) . . ?
C29 C34 N5 108.3(3) . . ?
C29 C34 C33 119.6(4) . . ?
N5 C34 C33 132.1(4) . . ?
O1 C35 N10 124.9(4) . . ?
N2 Co1 N5 172.10(14) . . ?
N2 Co1 N4 90.08(15) . . ?
N5 Co1 N4 91.23(15) . . ?
N2 Co1 N1 89.83(15) . . ?
N5 Co1 N1 91.82(15) . . ?
N4 Co1 N1 158.37(14) . . ?
N2 Co1 O1 83.27(15) . . ?
N5 Co1 O1 88.92(15) . . ?
N4 Co1 O1 108.29(14) . . ?
N1 Co1 O1 93.18(14) . . ?
C7 N1 C1 104.4(3) . . ?
C7 N1 Co1 124.3(3) . . ?
C1 N1 Co1 131.3(3) . . ?
C17 N2 C10 106.9(3) . . ?
C17 N2 Co1 125.9(3) . . ?
C10 N2 Co1 124.1(3) . . ?
C18 N3 C17 120.6(4) . . ?
C18 N4 C25 106.5(3) . . ?
C18 N4 Co1 125.0(3) . . ?
C25 N4 Co1 127.1(3) . . ?
C28 N5 C34 104.5(3) . . ?
C28 N5 Co1 127.1(3) . . ?
C34 N5 Co1 128.4(3) . . ?
C7 N6 C6 104.1(3) . . ?
C28 N7 C29 106.0(3) . . ?
C35 N10 C36 121.4(4) . . ?
C35 N10 C37 121.2(4) . . ?
C36 N10 C37 117.2(4) . . ?
C35 O1 Co1 125.0(3) . . ?

_refine_diff_density_max         0.490
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.082
# SQUEEZE RESULTS (Version = 300517)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
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 -0.003 0.000 0.000 142 40 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?



