# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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 2043926'
loop_
_audit_author_name
_audit_author_address
'Briana Schrage'
;The University of Akron
United States of America
;
_audit_update_record             
;
2020-11-11 deposited with the CCDC.	2020-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H20 N6 O'
_chemical_formula_weight         420.47

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      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'

_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'
'-y, x, z+1/4'
'y, -x, z+3/4'

_cell_length_a                   12.557(3)
_cell_length_b                   12.557
_cell_length_c                   25.933(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4089.2(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5839
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      22.96

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             1760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3464
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'twinabs 2008/2'
_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            5255
_diffrn_reflns_av_unetI/netI     0.1877
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.622
_diffrn_reflns_theta_max         28.457
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.507
_diffrn_reflns_point_group_measured_fraction_full 0.512
_reflns_number_total             5255
_reflns_number_gt                2621
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     0.000
_reflns_Friedel_fraction_full    0.000

_reflns_special_details          
; 
 _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-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1472P)²+13.2201P] 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 
; 
No quotients, so Flack parameter determined by classical intensity fit 
;
_refine_ls_abs_structure_Flack   0(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5255
_refine_ls_number_parameters     582
_refine_ls_number_restraints     67
_refine_ls_R_factor_all          0.2387
_refine_ls_R_factor_gt           0.1284
_refine_ls_wR_factor_ref         0.3539
_refine_ls_wR_factor_gt          0.2852
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.036
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2559(11) 0.8322(10) 0.4426(6) 0.035(3) Uani 1 1 d . . . . .
H1A H 0.180601 0.826671 0.440170 0.041 Uiso 1 1 calc R U . . .
C2 C 0.2957(13) 0.9332(10) 0.4461(6) 0.040(4) Uani 1 1 d . . . . .
H2 H 0.251147 0.994322 0.447209 0.048 Uiso 1 1 calc R U . . .
C3 C 0.4066(12) 0.9403(11) 0.4479(6) 0.037(4) Uani 1 1 d . . . . .
H3 H 0.438741 1.008635 0.449598 0.044 Uiso 1 1 calc R U . . .
C4 C 0.4689(11) 0.8542(10) 0.4474(6) 0.031(3) Uani 1 1 d . . . . .
H4 H 0.544105 0.860648 0.449848 0.038 Uiso 1 1 calc R U . . .
C5 C 0.4179(10) 0.7490(9) 0.4429(5) 0.025(3) Uani 1 1 d . . . . .
C6 C 0.4823(9) 0.6540(10) 0.4416(5) 0.026(3) Uani 1 1 d . . . . .
C7 C 0.5921(11) 0.6652(12) 0.4476(6) 0.033(3) Uani 1 1 d . . . . .
C8 C 0.4403(9) 0.5491(9) 0.4384(5) 0.021(3) Uani 1 1 d . U . . .
C9 C 0.4934(10) 0.4491(9) 0.4364(6) 0.026(3) Uani 1 1 d . . . . .
C10 C 0.5996(11) 0.4194(10) 0.4331(6) 0.031(3) Uani 1 1 d . . . . .
H10 H 0.652626 0.473288 0.434322 0.037 Uiso 1 1 calc R U . . .
C11 C 0.6309(11) 0.3152(10) 0.4280(5) 0.028(3) Uani 1 1 d . . . . .
H11 H 0.704137 0.296966 0.425349 0.034 Uiso 1 1 calc R U . . .
C12 C 0.5485(10) 0.2333(11) 0.4269(5) 0.029(3) Uani 1 1 d . . . . .
H12 H 0.567695 0.160290 0.424765 0.035 Uiso 1 1 calc R U . . .
C13 C 0.4380(10) 0.2636(10) 0.4290(5) 0.027(3) Uani 1 1 d . . . . .
H13 H 0.383078 0.211770 0.427039 0.032 Uiso 1 1 calc R U . . .
C14 C 0.4146(10) 0.3707(9) 0.4341(5) 0.024(3) Uani 1 1 d . . . . .
C15 C 0.3103(10) 0.4209(9) 0.4353(5) 0.021(3) Uani 1 1 d . . . . .
C16 C 0.2099(9) 0.3834(9) 0.4346(5) 0.019(3) Uani 1 1 d . . . . .
C17 C 0.1972(10) 0.2698(10) 0.4287(5) 0.026(3) Uani 1 1 d . . . . .
C18 C 0.1089(8) 0.4499(10) 0.4374(5) 0.020(3) Uani 1 1 d . . . . .
C19 C 0.0104(10) 0.4002(12) 0.4394(6) 0.036(4) Uani 1 1 d . . . . .
H19 H 0.005237 0.324676 0.439398 0.043 Uiso 1 1 calc R U . . .
C20 C -0.0809(10) 0.4632(12) 0.4413(6) 0.035(3) Uani 1 1 d . . . . .
H20 H -0.149921 0.432346 0.442200 0.042 Uiso 1 1 calc R U . . .
C21 C -0.0673(11) 0.5700(12) 0.4418(6) 0.036(4) Uani 1 1 d . . . . .
H21 H -0.127608 0.615415 0.443843 0.044 Uiso 1 1 calc R U . . .
C22 C 0.0336(9) 0.6136(10) 0.4393(6) 0.027(3) Uani 1 1 d . . . . .
H22 H 0.041182 0.688827 0.438316 0.032 Uiso 1 1 calc R U . . .
C23 C 0.4403(12) 0.7056(11) 0.5719(6) 0.036(3) Uani 1 1 d . . . . .
H23 H 0.515738 0.699414 0.572212 0.043 Uiso 1 1 calc R U . . .
C24 C 0.3982(11) 0.8064(12) 0.5733(6) 0.040(4) Uani 1 1 d . . . . .
H24 H 0.441864 0.868059 0.575391 0.048 Uiso 1 1 calc R U . . .
C25 C 0.2859(9) 0.8129(10) 0.5714(6) 0.027(3) Uani 1 1 d . . . . .
H25 H 0.253417 0.881172 0.572014 0.032 Uiso 1 1 calc R U . . .
C26 C 0.2240(11) 0.7272(10) 0.5689(6) 0.032(3) Uani 1 1 d . . . . .
H26 H 0.148796 0.733975 0.566786 0.038 Uiso 1 1 calc R U . . .
C27 C 0.2730(10) 0.6256(10) 0.5693(5) 0.024(3) Uani 1 1 d . . . . .
C28 C 0.2113(10) 0.5263(10) 0.5664(5) 0.024(3) Uani 1 1 d . U . . .
C29 C 0.0987(10) 0.5366(10) 0.5725(6) 0.027(3) Uani 1 1 d . . . . .
C30 C 0.2521(9) 0.4245(9) 0.5651(5) 0.022(3) Uani 1 1 d . U . . .
C31 C 0.2004(9) 0.3219(9) 0.5632(5) 0.019(2) Uani 1 1 d . U . . .
C32 C 0.0920(9) 0.2927(10) 0.5608(5) 0.024(3) Uani 1 1 d . . . . .
H32 H 0.037583 0.345224 0.560403 0.029 Uiso 1 1 calc R U . . .
C33 C 0.0670(10) 0.1849(10) 0.5590(5) 0.027(3) Uani 1 1 d . U . . .
H33 H -0.005633 0.163619 0.558578 0.032 Uiso 1 1 calc R U . . .
C34 C 0.1485(11) 0.1057(11) 0.5578(6) 0.034(3) Uani 1 1 d . . . . .
H34 H 0.129560 0.032450 0.556720 0.041 Uiso 1 1 calc R U . . .
C35 C 0.2544(11) 0.1343(9) 0.5583(6) 0.032(3) Uani 1 1 d . . . . .
H35 H 0.308642 0.081726 0.556584 0.038 Uiso 1 1 calc R U . . .
C36 C 0.2794(10) 0.2385(11) 0.5613(6) 0.028(3) Uani 1 1 d . . . . .
C37 C 0.3855(9) 0.2957(9) 0.5615(6) 0.022(3) Uani 1 1 d . . . . .
C38 C 0.4863(10) 0.2587(9) 0.5602(5) 0.024(3) Uani 1 1 d . . . . .
C39 C 0.5012(10) 0.1435(9) 0.5563(5) 0.023(3) Uani 1 1 d . U . . .
C40 C 0.5857(9) 0.3203(10) 0.5573(5) 0.022(3) Uani 1 1 d . U . . .
C41 C 0.6795(10) 0.2734(10) 0.5517(5) 0.026(3) Uani 1 1 d . . . . .
H41 H 0.683613 0.197962 0.550216 0.031 Uiso 1 1 calc R U . . .
C42 C 0.7753(10) 0.3360(12) 0.5480(6) 0.037(4) Uani 1 1 d . . . . .
H42 H 0.843435 0.304182 0.543885 0.045 Uiso 1 1 calc R U . . .
C43 C 0.7616(9) 0.4510(10) 0.5509(5) 0.021(3) Uani 1 1 d . . . . .
H43 H 0.820819 0.497824 0.548782 0.025 Uiso 1 1 calc R U . . .
C44 C 0.6607(9) 0.4888(10) 0.5566(5) 0.023(3) Uani 1 1 d . U . . .
H44 H 0.651112 0.563856 0.557684 0.027 Uiso 1 1 calc R U . . .
C45 C 0.7561(12) 0.9867(14) 0.4385(8) 0.054(5) Uani 1 1 d . . . . .
H45A H 0.739958 0.914961 0.451194 0.081 Uiso 1 1 calc R U . . .
H45B H 0.728574 0.994531 0.403306 0.081 Uiso 1 1 calc R U . . .
H45C H 0.722387 1.039567 0.460957 0.081 Uiso 1 1 calc R U . . .
C46 C 0.9382(15) 0.9132(13) 0.4276(8) 0.060(5) Uani 1 1 d . . . . .
H46A H 0.935535 0.897529 0.390585 0.090 Uiso 1 1 calc R U . . .
H46B H 0.911975 0.851648 0.447015 0.090 Uiso 1 1 calc R U . . .
H46C H 1.011848 0.928434 0.437689 0.090 Uiso 1 1 calc R U . . .
C47 C 0.9079(13) 1.0971(13) 0.4487(6) 0.044(4) Uani 1 1 d . . . . .
H47 H 0.982988 1.104214 0.451321 0.052 Uiso 1 1 calc R U . . .
C48 C 0.727(3) 0.834(3) 0.5703(13) 0.138(12) Uani 1 1 d . U . . .
H48A H 0.727118 0.762669 0.585783 0.207 Uiso 1 1 calc R U . . .
H48B H 0.692768 0.830734 0.536334 0.207 Uiso 1 1 calc R U . . .
H48C H 0.686706 0.882713 0.592601 0.207 Uiso 1 1 calc R U . . .
C49 C 0.820(2) 0.9846(15) 0.5748(9) 0.087(8) Uani 1 1 d . . . . .
H49A H 0.891410 1.016125 0.573399 0.131 Uiso 1 1 calc R U . . .
H49B H 0.788903 0.997104 0.608890 0.131 Uiso 1 1 calc R U . . .
H49C H 0.774949 1.017442 0.548347 0.131 Uiso 1 1 calc R U . . .
C50 C 0.910(2) 0.815(3) 0.5534(13) 0.124(10) Uani 1 1 d . U . . .
H50 H 0.906414 0.741912 0.544823 0.149 Uiso 1 1 calc R U . . .
N1 N 0.3334(7) 0.5307(8) 0.4388(4) 0.021(2) Uani 1 1 d . . . . .
H1 H 0.284827 0.580983 0.440977 0.025 Uiso 1 1 calc R U . . .
N2 N 0.1224(8) 0.5513(8) 0.4383(4) 0.027(3) Uani 1 1 d . . . . .
N3 N 0.1806(9) 0.1803(8) 0.4241(5) 0.034(3) Uani 1 1 d . . . . .
N4 N 0.3101(8) 0.7386(8) 0.4421(5) 0.030(3) Uani 1 1 d . . . . .
N5 N 0.6841(9) 0.6855(9) 0.4500(6) 0.040(3) Uani 1 1 d . . . . .
N6 N 0.3638(7) 0.4026(8) 0.5648(5) 0.023(2) Uani 1 1 d . . . . .
H6 H 0.413156 0.452138 0.566616 0.028 Uiso 1 1 calc R U . . .
N7 N 0.3828(8) 0.6138(8) 0.5701(5) 0.028(3) Uani 1 1 d . . . . .
N8 N 0.0104(9) 0.5510(10) 0.5764(6) 0.044(3) Uani 1 1 d . . . . .
N9 N 0.5732(7) 0.4265(7) 0.5609(4) 0.017(2) Uani 1 1 d . . . . .
N10 N 0.5183(9) 0.0537(9) 0.5538(5) 0.030(3) Uani 1 1 d . U . . .
N11 N 0.8733(8) 1.0032(9) 0.4384(5) 0.033(3) Uani 1 1 d . . . . .
N12 N 0.8275(10) 0.8691(11) 0.5653(5) 0.044(3) Uani 1 1 d . . . . .
O1 O 0.8572(9) 1.1772(8) 0.4555(5) 0.054(3) Uani 1 1 d . . . . .
O2 O 1.0052(8) 0.8717(10) 0.5537(6) 0.063(4) 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 1.368(18) . ?
C1 N4 1.358(16) . ?
C1 H1A 0.9500 . ?
C2 C3 1.40(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.334(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.473(17) . ?
C4 H4 0.9500 . ?
C5 N4 1.360(16) . ?
C5 C6 1.442(17) . ?
C6 C7 1.395(18) . ?
C6 C8 1.423(16) . ?
C7 N5 1.185(17) . ?
C8 N1 1.362(15) . ?
C8 C9 1.422(16) . ?
C9 C10 1.387(18) . ?
C9 C14 1.397(17) . ?
C10 C11 1.373(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.459(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.439(16) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.454(17) . ?
C15 C16 1.346(17) . ?
C15 N1 1.412(14) . ?
C16 C17 1.443(17) . ?
C16 C18 1.521(15) . ?
C17 N3 1.149(16) . ?
C18 N2 1.284(15) . ?
C18 C19 1.386(16) . ?
C19 C20 1.394(19) . ?
C19 H19 0.9500 . ?
C20 C21 1.35(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.381(18) . ?
C21 H21 0.9500 . ?
C22 N2 1.363(15) . ?
C22 H22 0.9500 . ?
C23 N7 1.361(17) . ?
C23 C24 1.37(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.413(18) . ?
C24 H24 0.9500 . ?
C25 C26 1.328(18) . ?
C25 H25 0.9500 . ?
C26 C27 1.417(18) . ?
C26 H26 0.9500 . ?
C27 N7 1.387(15) . ?
C27 C28 1.471(17) . ?
C28 C30 1.378(17) . ?
C28 C29 1.429(17) . ?
C29 N8 1.127(16) . ?
C30 N6 1.429(14) . ?
C30 C31 1.443(16) . ?
C31 C32 1.412(16) . ?
C31 C36 1.443(17) . ?
C32 C33 1.390(17) . ?
C32 H32 0.9500 . ?
C33 C34 1.429(19) . ?
C33 H33 0.9500 . ?
C34 C35 1.377(19) . ?
C34 H34 0.9500 . ?
C35 C36 1.348(17) . ?
C35 H35 0.9500 . ?
C36 C37 1.513(17) . ?
C37 C38 1.350(16) . ?
C37 N6 1.371(14) . ?
C38 C39 1.462(17) . ?
C38 C40 1.470(17) . ?
C39 N10 1.150(14) . ?
C40 C41 1.325(17) . ?
C40 N9 1.345(15) . ?
C41 C42 1.440(17) . ?
C41 H41 0.9500 . ?
C42 C43 1.46(2) . ?
C42 H42 0.9500 . ?
C43 C44 1.361(17) . ?
C43 H43 0.9500 . ?
C44 N9 1.354(15) . ?
C44 H44 0.9500 . ?
C45 N11 1.487(18) . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C46 N11 1.421(18) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 O1 1.203(18) . ?
C47 N11 1.285(18) . ?
C47 H47 0.9500 . ?
C48 N12 1.35(3) . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 N12 1.47(2) . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 N12 1.27(3) . ?
C50 O2 1.39(3) . ?
C50 H50 0.9500 . ?
N1 H1 0.8800 . ?
N6 H6 0.8800 . ?

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 N4 128.3(13) . . ?
C2 C1 H1A 115.8 . . ?
N4 C1 H1A 115.8 . . ?
C1 C2 C3 115.2(13) . . ?
C1 C2 H2 122.4 . . ?
C3 C2 H2 122.4 . . ?
C4 C3 C2 122.3(13) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 118.2(13) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
N4 C5 C6 118.6(10) . . ?
N4 C5 C4 121.4(11) . . ?
C6 C5 C4 120.0(11) . . ?
C7 C6 C5 118.0(11) . . ?
C7 C6 C8 117.8(12) . . ?
C5 C6 C8 124.0(11) . . ?
N5 C7 C6 172.5(16) . . ?
N1 C8 C9 108.2(11) . . ?
N1 C8 C6 121.5(10) . . ?
C9 C8 C6 130.2(11) . . ?
C10 C9 C14 119.2(11) . . ?
C10 C9 C8 133.7(12) . . ?
C14 C9 C8 107.0(11) . . ?
C11 C10 C9 122.6(12) . . ?
C11 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
C10 C11 C12 118.0(12) . . ?
C10 C11 H11 121.0 . . ?
C12 C11 H11 121.0 . . ?
C13 C12 C11 119.8(12) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C14 C13 C12 117.7(13) . . ?
C14 C13 H13 121.1 . . ?
C12 C13 H13 121.1 . . ?
C13 C14 C9 122.6(12) . . ?
C13 C14 C15 127.9(11) . . ?
C9 C14 C15 109.3(10) . . ?
C16 C15 N1 122.4(11) . . ?
C16 C15 C14 133.8(10) . . ?
N1 C15 C14 103.8(10) . . ?
C15 C16 C17 116.8(10) . . ?
C15 C16 C18 126.0(10) . . ?
C17 C16 C18 117.1(10) . . ?
N3 C17 C16 175.9(13) . . ?
N2 C18 C19 124.4(12) . . ?
N2 C18 C16 115.8(10) . . ?
C19 C18 C16 119.9(12) . . ?
C18 C19 C20 118.6(14) . . ?
C18 C19 H19 120.7 . . ?
C20 C19 H19 120.7 . . ?
C21 C20 C19 117.4(13) . . ?
C21 C20 H20 121.3 . . ?
C19 C20 H20 121.3 . . ?
C20 C21 C22 120.6(13) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
N2 C22 C21 121.6(12) . . ?
N2 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
N7 C23 C24 125.3(13) . . ?
N7 C23 H23 117.4 . . ?
C24 C23 H23 117.4 . . ?
C23 C24 C25 115.9(13) . . ?
C23 C24 H24 122.1 . . ?
C25 C24 H24 122.1 . . ?
C26 C25 C24 122.6(12) . . ?
C26 C25 H25 118.7 . . ?
C24 C25 H25 118.7 . . ?
C25 C26 C27 118.3(13) . . ?
C25 C26 H26 120.8 . . ?
C27 C26 H26 120.8 . . ?
N7 C27 C26 121.9(12) . . ?
N7 C27 C28 115.8(11) . . ?
C26 C27 C28 122.3(11) . . ?
C30 C28 C29 117.0(11) . . ?
C30 C28 C27 126.3(11) . . ?
C29 C28 C27 116.1(11) . . ?
N8 C29 C28 175.7(14) . . ?
C28 C30 N6 122.9(11) . . ?
C28 C30 C31 131.5(11) . . ?
N6 C30 C31 105.6(9) . . ?
C32 C31 C36 118.3(11) . . ?
C32 C31 C30 131.8(11) . . ?
C36 C31 C30 109.9(10) . . ?
C33 C32 C31 118.2(11) . . ?
C33 C32 H32 120.9 . . ?
C31 C32 H32 120.9 . . ?
C32 C33 C34 121.1(12) . . ?
C32 C33 H33 119.4 . . ?
C34 C33 H33 119.4 . . ?
C35 C34 C33 120.6(12) . . ?
C35 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C36 C35 C34 118.7(13) . . ?
C36 C35 H35 120.7 . . ?
C34 C35 H35 120.7 . . ?
C35 C36 C31 123.1(12) . . ?
C35 C36 C37 131.8(12) . . ?
C31 C36 C37 105.1(11) . . ?
C38 C37 N6 121.7(11) . . ?
C38 C37 C36 131.5(11) . . ?
N6 C37 C36 106.8(10) . . ?
C37 C38 C39 117.5(11) . . ?
C37 C38 C40 128.0(11) . . ?
C39 C38 C40 114.2(11) . . ?
N10 C39 C38 176.5(14) . . ?
C41 C40 N9 123.5(11) . . ?
C41 C40 C38 121.7(11) . . ?
N9 C40 C38 114.8(10) . . ?
C40 C41 C42 120.5(12) . . ?
C40 C41 H41 119.7 . . ?
C42 C41 H41 119.7 . . ?
C41 C42 C43 116.0(12) . . ?
C41 C42 H42 122.0 . . ?
C43 C42 H42 122.0 . . ?
C44 C43 C42 117.6(11) . . ?
C44 C43 H43 121.2 . . ?
C42 C43 H43 121.2 . . ?
N9 C44 C43 124.2(11) . . ?
N9 C44 H44 117.9 . . ?
C43 C44 H44 117.9 . . ?
N11 C45 H45A 109.5 . . ?
N11 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
N11 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
N11 C46 H46A 109.5 . . ?
N11 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
N11 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
O1 C47 N11 128.3(15) . . ?
O1 C47 H47 115.9 . . ?
N11 C47 H47 115.9 . . ?
N12 C48 H48A 109.5 . . ?
N12 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
N12 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
N12 C49 H49A 109.5 . . ?
N12 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
N12 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
N12 C50 O2 115(3) . . ?
N12 C50 H50 122.3 . . ?
O2 C50 H50 122.3 . . ?
C8 N1 C15 111.6(10) . . ?
C8 N1 H1 124.2 . . ?
C15 N1 H1 124.2 . . ?
C18 N2 C22 117.4(10) . . ?
C5 N4 C1 114.6(11) . . ?
C37 N6 C30 112.6(9) . . ?
C37 N6 H6 123.7 . . ?
C30 N6 H6 123.7 . . ?
C23 N7 C27 116.0(11) . . ?
C40 N9 C44 118.2(10) . . ?
C47 N11 C46 125.3(13) . . ?
C47 N11 C45 117.5(13) . . ?
C46 N11 C45 117.2(14) . . ?
C50 N12 C48 128(2) . . ?
C50 N12 C49 128(2) . . ?
C48 N12 C49 104(2) . . ?

_refine_diff_density_max         0.783
_refine_diff_density_min         -0.517
_refine_diff_density_rms         0.101

####################################################################### 
# 
# 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_Ni1
_database_code_depnum_ccdc_archive 'CCDC 2043929'
loop_
_audit_author_name
_audit_author_address
'Briana Schrage'
;The University of Akron
United States of America
;
_audit_update_record             
;
2020-11-11 deposited with the CCDC.	2020-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H24 N10 Ni'
_chemical_formula_weight         751.44

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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           142
_space_group_name_H-M_alt        'I 41/a c d'
_space_group_name_Hall           '-I 4bd 2c'

_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'
'-y+1/4, x+3/4, z+1/4'
'y+1/4, -x+1/4, z+3/4'
'-x+1/2, y, -z'
'x, -y, -z+1/2'
'y+1/4, x+3/4, -z+3/4'
'-y+1/4, -x+1/4, -z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+3/4, x+5/4, z+3/4'
'y+3/4, -x+3/4, z+5/4'
'-x+1, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1'
'y+3/4, x+5/4, -z+5/4'
'-y+3/4, -x+3/4, -z+3/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-1/4, -x-3/4, -z-1/4'
'-y-1/4, x-1/4, -z-3/4'
'x-1/2, -y, z'
'-x, y, z-1/2'
'-y-1/4, -x-3/4, z-3/4'
'y-1/4, x-1/4, z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y+1/4, -x-1/4, -z+1/4'
'-y+1/4, x+1/4, -z-1/4'
'x, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'
'-y+1/4, -x-1/4, z-1/4'
'y+1/4, x+1/4, z+1/4'

_cell_length_a                   17.9413(11)
_cell_length_b                   17.9413(11)
_cell_length_c                   42.212(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     13587.6(18)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1610
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      28.01

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_F_000             6176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.208
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.095
_exptl_absorpt_coefficient_mu    0.623
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6479
_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            15457
_diffrn_reflns_av_unetI/netI     0.1334
_diffrn_reflns_av_R_equivalents  0.1368
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_theta_min         1.873
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.049
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3006
_reflns_number_gt                1842
_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 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0237P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3006
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1089
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1154
_refine_ls_wR_factor_gt          0.1009
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_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 0.7482(2) 0.4662(2) 0.79524(8) 0.0185(9) Uani 1 1 d . . . . .
H1 H 0.746815 0.422492 0.782541 0.022 Uiso 1 1 calc R U . . .
C2 C 0.7084(2) 0.4662(2) 0.82283(8) 0.0231(10) Uani 1 1 d . . . . .
H2 H 0.679731 0.423992 0.828866 0.028 Uiso 1 1 calc R U . . .
C3 C 0.7110(2) 0.5286(2) 0.84165(8) 0.0223(10) Uani 1 1 d . . . . .
H3 H 0.685458 0.529668 0.861358 0.027 Uiso 1 1 calc R U . . .
C4 C 0.7511(2) 0.5895(2) 0.83156(8) 0.0185(9) Uani 1 1 d . . . . .
H4 H 0.753435 0.632948 0.844371 0.022 Uiso 1 1 calc R U . . .
C5 C 0.7886(2) 0.5876(2) 0.80251(8) 0.0148(9) Uani 1 1 d . . . . .
C6 C 0.8224(2) 0.6557(2) 0.79000(7) 0.0143(9) Uani 1 1 d . . . . .
C7 C 0.8165(2) 0.7198(2) 0.81011(8) 0.0224(10) Uani 1 1 d . . . . .
C8 C 0.8522(2) 0.6668(2) 0.76004(8) 0.0149(9) Uani 1 1 d . . . . .
C9 C 0.8652(2) 0.7389(2) 0.74396(7) 0.0168(9) Uani 1 1 d . . . . .
C10 C 0.8592(2) 0.8121(2) 0.75372(8) 0.0200(10) Uani 1 1 d . . . . .
H10 H 0.843089 0.823976 0.774569 0.024 Uiso 1 1 calc R U . . .
C11 C 0.8774(2) 0.8686(2) 0.73207(8) 0.0207(9) Uani 1 1 d . . . . .
H11 H 0.873719 0.919347 0.738267 0.025 Uiso 1 1 calc R U . . .
C12 C 0.9007(2) 0.8507(2) 0.70154(8) 0.0213(10) Uani 1 1 d . . . . .
H12 H 0.914069 0.889471 0.687312 0.026 Uiso 1 1 calc R U . . .
C13 C 0.9047(2) 0.7780(2) 0.69169(8) 0.0188(9) Uani 1 1 d . . . . .
H13 H 0.919919 0.766346 0.670706 0.023 Uiso 1 1 calc R U . . .
C14 C 0.8862(2) 0.7217(2) 0.71285(8) 0.0164(9) Uani 1 1 d . . . . .
C15 C 0.89041(19) 0.6402(2) 0.71092(7) 0.0159(9) Uani 1 1 d . . . . .
C16 C 0.9139(2) 0.5990(2) 0.68504(7) 0.0136(9) Uani 1 1 d . . . . .
C17 C 0.9079(2) 0.6345(2) 0.65446(8) 0.0198(10) Uani 1 1 d . . . . .
C18 C 0.9462(2) 0.5247(2) 0.68502(7) 0.0157(9) Uani 1 1 d . . . . .
C19 C 0.9787(2) 0.4959(2) 0.65721(8) 0.0208(10) Uani 1 1 d . . . . .
H19 H 0.975471 0.523329 0.638015 0.025 Uiso 1 1 calc R U . . .
C20 C 1.0146(2) 0.4289(2) 0.65757(8) 0.0236(10) Uani 1 1 d . . . . .
H20 H 1.035096 0.409029 0.638617 0.028 Uiso 1 1 calc R U . . .
C21 C 1.0211(2) 0.3902(2) 0.68581(8) 0.0242(10) Uani 1 1 d . . . . .
H21 H 1.046669 0.343951 0.686875 0.029 Uiso 1 1 calc R U . . .
C22 C 0.9889(2) 0.4215(2) 0.71234(8) 0.0208(10) Uani 1 1 d . . . . .
H22 H 0.995056 0.396150 0.731922 0.025 Uiso 1 1 calc R U . . .
N1 N 0.87112(17) 0.61012(17) 0.73958(6) 0.0153(7) Uani 1 1 d . . . . .
N2 N 0.78905(17) 0.52398(17) 0.78488(6) 0.0143(7) Uani 1 1 d . . . . .
N3 N 0.94957(17) 0.48486(17) 0.71253(6) 0.0165(8) Uani 1 1 d . . . . .
N4 N 0.8134(2) 0.7696(2) 0.82727(7) 0.0317(10) Uani 1 1 d . . . . .
N5 N 0.89917(19) 0.65846(19) 0.62972(7) 0.0274(9) Uani 1 1 d . . . . .
Ni1 Ni 0.87073(4) 0.500000 0.750000 0.0145(2) Uani 1 2 d S T P . .


_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 N2 1.343(5) . ?
C1 C2 1.366(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.374(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.376(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(5) . ?
C4 H4 0.9500 . ?
C5 N2 1.362(4) . ?
C5 C6 1.463(5) . ?
C6 C8 1.388(4) . ?
C6 C7 1.434(5) . ?
C7 N4 1.151(5) . ?
C8 N1 1.377(4) . ?
C8 C9 1.480(5) . ?
C9 C10 1.381(5) . ?
C9 C14 1.401(5) . ?
C10 C11 1.403(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.393(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.370(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.466(5) . ?
C15 N1 1.369(4) . ?
C15 C16 1.385(5) . ?
C16 C17 1.443(5) . ?
C16 C18 1.454(5) . ?
C17 N5 1.140(4) . ?
C18 N3 1.365(4) . ?
C18 C19 1.409(5) . ?
C19 C20 1.363(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.384(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.379(5) . ?
C21 H21 0.9500 . ?
C22 N3 1.338(5) . ?
C22 H22 0.9500 . ?
N1 Ni1 2.024(3) . ?
N2 Ni1 2.121(3) . ?
N3 Ni1 2.139(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
N2 C1 C2 124.3(4) . . ?
N2 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C1 C2 C3 118.4(4) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 119.1(4) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 120.2(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N2 C5 C4 120.1(3) . . ?
N2 C5 C6 120.0(3) . . ?
C4 C5 C6 119.7(3) . . ?
C8 C6 C7 116.9(3) . . ?
C8 C6 C5 127.5(3) . . ?
C7 C6 C5 115.2(3) . . ?
N4 C7 C6 176.9(4) . . ?
N1 C8 C6 124.1(3) . . ?
N1 C8 C9 108.6(3) . . ?
C6 C8 C9 127.2(3) . . ?
C10 C9 C14 120.7(3) . . ?
C10 C9 C8 133.0(3) . . ?
C14 C9 C8 106.2(3) . . ?
C9 C10 C11 118.3(3) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 H10 120.9 . . ?
C12 C11 C10 120.4(4) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 121.1(4) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 119.0(3) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C13 C14 C9 120.5(4) . . ?
C13 C14 C15 132.6(3) . . ?
C9 C14 C15 106.6(3) . . ?
N1 C15 C16 124.3(3) . . ?
N1 C15 C14 109.4(3) . . ?
C16 C15 C14 126.3(3) . . ?
C15 C16 C17 116.6(3) . . ?
C15 C16 C18 127.7(3) . . ?
C17 C16 C18 115.7(3) . . ?
N5 C17 C16 174.8(4) . . ?
N3 C18 C19 119.9(4) . . ?
N3 C18 C16 119.8(3) . . ?
C19 C18 C16 120.1(3) . . ?
C20 C19 C18 120.7(3) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 119.4(4) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C22 C21 C20 117.4(4) . . ?
C22 C21 H21 121.3 . . ?
C20 C21 H21 121.3 . . ?
N3 C22 C21 124.8(4) . . ?
N3 C22 H22 117.6 . . ?
C21 C22 H22 117.6 . . ?
C15 N1 C8 109.0(3) . . ?
C15 N1 Ni1 125.3(2) . . ?
C8 N1 Ni1 125.7(2) . . ?
C1 N2 C5 117.7(3) . . ?
C1 N2 Ni1 116.5(2) . . ?
C5 N2 Ni1 123.6(3) . . ?
C22 N3 C18 117.6(3) . . ?
C22 N3 Ni1 117.4(2) . . ?
C18 N3 Ni1 122.2(3) . . ?
N1 Ni1 N1 179.60(18) . 6_566 ?
N1 Ni1 N2 87.44(11) . . ?
N1 Ni1 N2 92.84(12) 6_566 . ?
N1 Ni1 N2 92.83(12) . 6_566 ?
N1 Ni1 N2 87.44(12) 6_566 6_566 ?
N2 Ni1 N2 92.62(16) . 6_566 ?
N1 Ni1 N3 87.76(11) . . ?
N1 Ni1 N3 91.98(12) 6_566 . ?
N2 Ni1 N3 174.66(11) . . ?
N2 Ni1 N3 85.29(11) 6_566 . ?
N1 Ni1 N3 91.98(12) . 6_566 ?
N1 Ni1 N3 87.76(11) 6_566 6_566 ?
N2 Ni1 N3 85.28(11) . 6_566 ?
N2 Ni1 N3 174.66(11) 6_566 6_566 ?
N3 Ni1 N3 97.22(16) . 6_566 ?

_refine_diff_density_max         0.308
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_Zn1
_database_code_depnum_ccdc_archive 'CCDC 2043927'
loop_
_audit_author_name
_audit_author_address
'Briana Schrage'
;The University of Akron
United States of America
;
_audit_update_record             
;
2020-11-11 deposited with the CCDC.	2020-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H15 N5 O2 Zn'
_chemical_formula_weight         470.78

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'
Zn Zn 0.2839 1.4301 '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                   7.9525(11)
_cell_length_b                   10.8324(15)
_cell_length_c                   12.7721(19)
_cell_angle_alpha                69.282(8)
_cell_angle_beta                 75.267(9)
_cell_angle_gamma                83.931(9)
_cell_volume                     995.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3742
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      25.50

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.133
_exptl_crystal_size_min          0.106
_exptl_absorpt_coefficient_mu    1.268
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6098
_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            15222
_diffrn_reflns_av_unetI/netI     0.1190
_diffrn_reflns_av_R_equivalents  0.1113
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.753
_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             3577
_reflns_number_gt                2143
_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 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1242P)²+7.3236P] 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         3577
_refine_ls_number_parameters     290
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1511
_refine_ls_R_factor_gt           0.0922
_refine_ls_wR_factor_ref         0.2727
_refine_ls_wR_factor_gt          0.2340
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.049
_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 0.6483(13) 0.0114(9) 0.6765(9) 0.032(2) Uani 1 1 d . . . . .
H1 H 0.631694 -0.018252 0.757779 0.039 Uiso 1 1 calc R U . . .
C2 C 0.7682(13) -0.0533(10) 0.6172(10) 0.041(3) Uani 1 1 d . . . . .
H2 H 0.834522 -0.125078 0.656040 0.049 Uiso 1 1 calc R U . . .
C3 C 0.7911(13) -0.0134(10) 0.5015(10) 0.036(2) Uani 1 1 d . . . . .
H3 H 0.873665 -0.057776 0.458330 0.043 Uiso 1 1 calc R U . . .
C4 C 0.6959(12) 0.0904(9) 0.4467(8) 0.028(2) Uani 1 1 d . . . . .
H4 H 0.710303 0.117694 0.365653 0.034 Uiso 1 1 calc R U . . .
C5 C 0.5762(12) 0.1567(9) 0.5113(7) 0.024(2) Uani 1 1 d . . . . .
C6 C 0.4749(12) 0.2713(8) 0.4513(7) 0.024(2) Uani 1 1 d . . . . .
C7 C 0.4991(12) 0.2927(9) 0.3294(8) 0.028(2) Uani 1 1 d . . . . .
C8 C 0.3743(12) 0.3584(9) 0.4951(7) 0.024(2) Uani 1 1 d . . . . .
C9 C 0.2868(12) 0.4811(8) 0.4337(7) 0.024(2) Uani 1 1 d . . . . .
C10 C 0.2779(12) 0.5409(9) 0.3196(8) 0.029(2) Uani 1 1 d . . . . .
H10 H 0.333791 0.502477 0.263018 0.035 Uiso 1 1 calc R U . . .
C11 C 0.1838(13) 0.6595(9) 0.2910(8) 0.032(2) Uani 1 1 d . . . . .
H11 H 0.175979 0.702047 0.213294 0.039 Uiso 1 1 calc R U . . .
C12 C 0.1021(13) 0.7170(9) 0.3713(8) 0.029(2) Uani 1 1 d . . . . .
H12 H 0.039772 0.798033 0.348064 0.035 Uiso 1 1 calc R U . . .
C13 C 0.1095(12) 0.6582(8) 0.4864(8) 0.026(2) Uani 1 1 d . . . . .
H13 H 0.052918 0.697752 0.542082 0.031 Uiso 1 1 calc R U . . .
C14 C 0.2036(11) 0.5384(8) 0.5176(7) 0.023(2) Uani 1 1 d . . . . .
C15 C 0.2401(11) 0.4514(8) 0.6286(7) 0.0194(18) Uani 1 1 d . . . . .
C16 C 0.1993(11) 0.4696(8) 0.7315(7) 0.0186(18) Uani 1 1 d . . . . .
C17 C 0.0884(12) 0.5811(9) 0.7426(7) 0.025(2) Uani 1 1 d . . . . .
C18 C 0.2661(11) 0.3950(8) 0.8347(7) 0.0218(19) Uani 1 1 d . . . . .
C19 C 0.2492(12) 0.4470(9) 0.9228(7) 0.027(2) Uani 1 1 d . . . . .
H19 H 0.182856 0.525769 0.920617 0.032 Uiso 1 1 calc R U . . .
C20 C 0.3274(12) 0.3852(9) 1.0119(8) 0.028(2) Uani 1 1 d . . . . .
H20 H 0.317529 0.421391 1.071005 0.034 Uiso 1 1 calc R U . . .
C21 C 0.4206(13) 0.2701(9) 1.0153(7) 0.030(2) Uani 1 1 d . . . . .
H21 H 0.479976 0.227290 1.074814 0.036 Uiso 1 1 calc R U . . .
C22 C 0.4259(12) 0.2181(9) 0.9304(8) 0.028(2) Uani 1 1 d . . . . .
H22 H 0.486490 0.136746 0.934460 0.034 Uiso 1 1 calc R U . . .
C23 C 0.1997(13) -0.0218(10) 0.8469(9) 0.035(2) Uani 1 1 d . U . . .
C24 C 0.0801(17) -0.1481(13) 0.9254(11) 0.060(3) Uani 1 1 d . U . . .
H24A H -0.038553 -0.118300 0.951995 0.090 Uiso 1 1 calc R U . . .
H24B H 0.128000 -0.198895 0.991955 0.090 Uiso 1 1 calc R U . . .
H24C H 0.078149 -0.203991 0.879812 0.090 Uiso 1 1 calc R U . . .
N1 N 0.3384(9) 0.3470(6) 0.6084(6) 0.0196(16) Uani 1 1 d . . . . .
N2 N 0.5506(10) 0.1159(7) 0.6268(6) 0.0274(18) Uani 1 1 d . . . . .
N3 N 0.3494(10) 0.2771(7) 0.8422(6) 0.0244(17) Uani 1 1 d . . . . .
N4 N 0.5218(11) 0.3051(8) 0.2344(7) 0.038(2) Uani 1 1 d . . . . .
N5 N 0.0038(11) 0.6677(8) 0.7534(7) 0.0307(19) Uani 1 1 d . . . . .
O1 O 0.1472(10) 0.0608(7) 0.7750(6) 0.0422(18) Uani 1 1 d . . . . .
O2 O 0.3312(10) -0.0184(7) 0.8800(6) 0.0429(18) Uani 1 1 d . . . . .
Zn1 Zn 0.35373(16) 0.17751(11) 0.73402(10) 0.0335(4) 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 1.356(14) . ?
C1 N2 1.358(11) . ?
C1 H1 0.9500 . ?
C2 C3 1.353(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.364(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.406(13) . ?
C4 H4 0.9500 . ?
C5 N2 1.348(11) . ?
C5 C6 1.486(12) . ?
C6 C8 1.352(12) . ?
C6 C7 1.454(13) . ?
C7 N4 1.141(11) . ?
C8 N1 1.365(11) . ?
C8 C9 1.487(12) . ?
C9 C10 1.386(12) . ?
C9 C14 1.412(12) . ?
C10 C11 1.396(13) . ?
C10 H10 0.9500 . ?
C11 C12 1.375(14) . ?
C11 H11 0.9500 . ?
C12 C13 1.394(12) . ?
C12 H12 0.9500 . ?
C13 C14 1.409(12) . ?
C13 H13 0.9500 . ?
C14 C15 1.480(11) . ?
C15 C16 1.350(11) . ?
C15 N1 1.369(10) . ?
C16 C17 1.445(12) . ?
C16 C18 1.478(11) . ?
C17 N5 1.124(11) . ?
C18 N3 1.359(11) . ?
C18 C19 1.399(12) . ?
C19 C20 1.365(12) . ?
C19 H19 0.9500 . ?
C20 C21 1.374(13) . ?
C20 H20 0.9500 . ?
C21 C22 1.377(12) . ?
C21 H21 0.9500 . ?
C22 N3 1.344(11) . ?
C22 H22 0.9500 . ?
C23 O1 1.164(12) . ?
C23 O2 1.232(11) . ?
C23 C24 1.613(16) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
N1 Zn1 1.981(6) . ?
N2 Zn1 2.027(8) . ?
N3 Zn1 2.023(7) . ?
O1 Zn1 2.025(7) . ?
O2 Zn1 2.264(7) . ?

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 N2 124.1(10) . . ?
C2 C1 H1 118.0 . . ?
N2 C1 H1 118.0 . . ?
C3 C2 C1 118.5(10) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 120.1(9) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 119.4(9) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N2 C5 C4 120.7(8) . . ?
N2 C5 C6 119.9(8) . . ?
C4 C5 C6 119.4(8) . . ?
C8 C6 C7 118.5(8) . . ?
C8 C6 C5 127.8(8) . . ?
C7 C6 C5 113.6(8) . . ?
N4 C7 C6 177.4(10) . . ?
C6 C8 N1 123.8(8) . . ?
C6 C8 C9 128.5(8) . . ?
N1 C8 C9 107.7(7) . . ?
C10 C9 C14 121.1(8) . . ?
C10 C9 C8 132.9(8) . . ?
C14 C9 C8 106.0(7) . . ?
C9 C10 C11 117.5(9) . . ?
C9 C10 H10 121.3 . . ?
C11 C10 H10 121.3 . . ?
C12 C11 C10 122.3(8) . . ?
C12 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
C11 C12 C13 121.0(8) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C12 C13 C14 117.9(8) . . ?
C12 C13 H13 121.1 . . ?
C14 C13 H13 121.1 . . ?
C13 C14 C9 120.2(8) . . ?
C13 C14 C15 132.4(8) . . ?
C9 C14 C15 107.3(7) . . ?
C16 C15 N1 123.6(7) . . ?
C16 C15 C14 129.2(8) . . ?
N1 C15 C14 107.1(7) . . ?
C15 C16 C17 118.0(7) . . ?
C15 C16 C18 127.8(8) . . ?
C17 C16 C18 114.0(7) . . ?
N5 C17 C16 178.3(9) . . ?
N3 C18 C19 119.9(7) . . ?
N3 C18 C16 119.6(7) . . ?
C19 C18 C16 120.4(7) . . ?
C20 C19 C18 120.4(8) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 119.4(8) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C20 C21 C22 118.5(8) . . ?
C20 C21 H21 120.8 . . ?
C22 C21 H21 120.8 . . ?
N3 C22 C21 123.1(8) . . ?
N3 C22 H22 118.4 . . ?
C21 C22 H22 118.4 . . ?
O1 C23 O2 127.0(10) . . ?
O1 C23 C24 118.7(10) . . ?
O2 C23 C24 113.9(9) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C8 N1 C15 111.8(7) . . ?
C8 N1 Zn1 123.4(6) . . ?
C15 N1 Zn1 121.8(5) . . ?
C5 N2 C1 117.1(8) . . ?
C5 N2 Zn1 125.3(6) . . ?
C1 N2 Zn1 116.8(6) . . ?
C22 N3 C18 118.6(7) . . ?
C22 N3 Zn1 117.2(6) . . ?
C18 N3 Zn1 124.2(5) . . ?
C23 O1 Zn1 93.0(7) . . ?
C23 O2 Zn1 80.3(6) . . ?
N1 Zn1 N3 89.9(3) . . ?
N1 Zn1 O1 112.7(3) . . ?
N3 Zn1 O1 115.5(3) . . ?
N1 Zn1 N2 90.2(3) . . ?
N3 Zn1 N2 132.5(3) . . ?
O1 Zn1 N2 108.0(3) . . ?
N1 Zn1 O2 172.0(3) . . ?
N3 Zn1 O2 91.5(3) . . ?
O1 Zn1 O2 59.7(3) . . ?
N2 Zn1 O2 94.6(3) . . ?

_refine_diff_density_max         2.496
_refine_diff_density_min         -0.840
_refine_diff_density_rms         0.162

####################################################################### 
# 
# 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_Cu1
_database_code_depnum_ccdc_archive 'CCDC 2043928'
loop_
_audit_author_name
_audit_author_address
'Briana Schrage'
;The University of Akron
United States of America
;
_audit_update_record             
;
2020-11-11 deposited with the CCDC.	2020-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H19 Cl Cu N6 O5'
_chemical_formula_weight         582.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.025
_cell_length_b                   28.235
_cell_length_c                   10.565
_cell_angle_alpha                90
_cell_angle_beta                 101.66
_cell_angle_gamma                90
_cell_volume                     2344.4
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9682
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.62

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_F_000             1188
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.587
_exptl_crystal_size_mid          0.266
_exptl_crystal_size_min          0.078
_exptl_absorpt_coefficient_mu    1.098
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6217
_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            51946
_diffrn_reflns_av_unetI/netI     0.0903
_diffrn_reflns_av_R_equivalents  0.1304
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.442
_diffrn_reflns_theta_max         28.278
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5789
_reflns_number_gt                4385
_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 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+47.4349P] 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         5789
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1248
_refine_ls_R_factor_gt           0.0988
_refine_ls_wR_factor_ref         0.2402
_refine_ls_wR_factor_gt          0.2303
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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 -0.0173(9) 0.3725(3) 0.5650(7) 0.0179(14) Uani 1 1 d . . . . .
H1 H 0.071842 0.349796 0.575343 0.021 Uiso 1 1 calc R U . . .
C2 C -0.1783(10) 0.3594(3) 0.4970(7) 0.0195(14) Uani 1 1 d . . . . .
H2 H -0.198365 0.328507 0.461421 0.023 Uiso 1 1 calc R U . . .
C3 C -0.3076(9) 0.3924(3) 0.4827(7) 0.0176(14) Uani 1 1 d . . . . .
H3 H -0.420217 0.384039 0.441540 0.021 Uiso 1 1 calc R U . . .
C4 C -0.2711(8) 0.4376(2) 0.5289(6) 0.0138(13) Uani 1 1 d . . . . .
H4 H -0.357470 0.461176 0.515420 0.017 Uiso 1 1 calc R U . . .
C5 C -0.1056(8) 0.4492(2) 0.5964(6) 0.0132(13) Uani 1 1 d . . . . .
C6 C -0.0680(8) 0.4980(2) 0.6462(6) 0.0134(13) Uani 1 1 d . . . . .
C7 C -0.2096(8) 0.5296(2) 0.6122(7) 0.0169(14) Uani 1 1 d . . . . .
C8 C 0.0837(8) 0.5155(2) 0.7109(6) 0.0119(12) Uani 1 1 d . . . . .
C9 C 0.1211(8) 0.5646(2) 0.7597(6) 0.0128(13) Uani 1 1 d . . . . .
C10 C 0.0177(9) 0.6044(2) 0.7596(6) 0.0164(14) Uani 1 1 d . . . . .
H10 H -0.100852 0.603007 0.724289 0.020 Uiso 1 1 calc R U . . .
C11 C 0.0934(9) 0.6463(3) 0.8126(7) 0.0182(14) Uani 1 1 d . . . . .
H11 H 0.024985 0.673505 0.816065 0.022 Uiso 1 1 calc R U . . .
C12 C 0.2686(9) 0.6487(3) 0.8607(7) 0.0186(14) Uani 1 1 d . . . . .
H12 H 0.318074 0.677742 0.894669 0.022 Uiso 1 1 calc R U . . .
C13 C 0.3727(9) 0.6088(3) 0.8597(7) 0.0166(14) Uani 1 1 d . . . . .
H13 H 0.492169 0.610690 0.890929 0.020 Uiso 1 1 calc R U . . .
C14 C 0.2959(8) 0.5662(2) 0.8115(6) 0.0147(13) Uani 1 1 d . . . . .
C15 C 0.3645(8) 0.5183(2) 0.8009(6) 0.0118(12) Uani 1 1 d . . . . .
C16 C 0.5274(8) 0.5026(2) 0.8454(6) 0.0136(13) Uani 1 1 d . . . . .
C17 C 0.6497(8) 0.5355(2) 0.9160(7) 0.0157(14) Uani 1 1 d . . . . .
C18 C 0.5979(8) 0.4551(2) 0.8379(6) 0.0126(12) Uani 1 1 d . . . . .
C19 C 0.7726(9) 0.4462(3) 0.8843(7) 0.0178(14) Uani 1 1 d . . . . .
H19 H 0.844181 0.471231 0.923038 0.021 Uiso 1 1 calc R U . . .
C20 C 0.8404(8) 0.4027(3) 0.8748(7) 0.0174(14) Uani 1 1 d . . . . .
H20 H 0.957417 0.396996 0.909377 0.021 Uiso 1 1 calc R U . . .
C21 C 0.7347(9) 0.3657(3) 0.8127(7) 0.0188(14) Uani 1 1 d . . . . .
H21 H 0.779584 0.335256 0.800757 0.023 Uiso 1 1 calc R U . . .
C22 C 0.5653(9) 0.3756(3) 0.7707(7) 0.0175(14) Uani 1 1 d . . . . .
H22 H 0.492940 0.351030 0.729914 0.021 Uiso 1 1 calc R U . . .
C23 C 0.2508(8) 0.3386(3) 0.9034(7) 0.0161(14) Uani 1 1 d . . . . .
H23 H 0.252620 0.358956 0.975235 0.019 Uiso 1 1 calc R U . . .
C24 C 0.3096(10) 0.2740(3) 1.0596(7) 0.0235(16) Uani 1 1 d . . . . .
H24A H 0.309939 0.300062 1.120942 0.035 Uiso 1 1 calc R U . . .
H24B H 0.419180 0.257473 1.079511 0.035 Uiso 1 1 calc R U . . .
H24C H 0.217982 0.251807 1.066391 0.035 Uiso 1 1 calc R U . . .
C25 C 0.2813(11) 0.2595(3) 0.8212(7) 0.0232(16) Uani 1 1 d . . . . .
H25A H 0.187084 0.237153 0.817809 0.035 Uiso 1 1 calc R U . . .
H25B H 0.389247 0.242155 0.836566 0.035 Uiso 1 1 calc R U . . .
H25C H 0.267052 0.276566 0.738916 0.035 Uiso 1 1 calc R U . . .
Cl1 Cl 0.3299(2) 0.28269(7) 0.44013(18) 0.0230(4) Uani 1 1 d . . . . .
Cu1 Cu 0.24312(10) 0.42204(3) 0.73381(8) 0.0149(2) Uani 1 1 d . . . . .
N1 N 0.2317(7) 0.49011(19) 0.7402(5) 0.0110(10) Uani 1 1 d . . . . .
N2 N 0.0172(7) 0.4157(2) 0.6164(5) 0.0141(11) Uani 1 1 d . . . . .
N3 N 0.4949(7) 0.4189(2) 0.7845(5) 0.0137(11) Uani 1 1 d . . . . .
N4 N -0.3257(8) 0.5543(3) 0.5788(8) 0.0338(18) Uani 1 1 d . . . . .
N5 N 0.7543(8) 0.5593(2) 0.9760(6) 0.0216(13) Uani 1 1 d . . . . .
N6 N 0.2820(7) 0.2933(2) 0.9259(6) 0.0160(12) Uani 1 1 d . . . . .
O1 O 0.2190(6) 0.35629(17) 0.7928(5) 0.0183(10) Uani 1 1 d . . . . .
O2 O 0.4541(8) 0.2964(3) 0.5521(6) 0.0408(16) Uani 1 1 d . . . . .
O3 O 0.3020(11) 0.3224(3) 0.3533(8) 0.058(2) Uani 1 1 d . . . . .
O4 O 0.1728(9) 0.2704(3) 0.4790(8) 0.058(2) Uani 1 1 d . . . . .
O5 O 0.3912(9) 0.2436(2) 0.3759(8) 0.0463(18) 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 N2 1.340(9) . ?
C1 C2 1.395(10) . ?
C1 H1 0.9500 . ?
C2 C3 1.380(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.412(9) . ?
C4 H4 0.9500 . ?
C5 N2 1.351(9) . ?
C5 C6 1.485(9) . ?
C6 C8 1.363(9) . ?
C6 C7 1.432(9) . ?
C7 N4 1.161(10) . ?
C8 N1 1.368(8) . ?
C8 C9 1.488(9) . ?
C9 C10 1.397(9) . ?
C9 C14 1.399(9) . ?
C10 C11 1.393(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.397(10) . ?
C11 H11 0.9500 . ?
C12 C13 1.403(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.401(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.473(9) . ?
C15 C16 1.370(9) . ?
C15 N1 1.379(8) . ?
C16 C17 1.445(9) . ?
C16 C18 1.465(9) . ?
C17 N5 1.157(9) . ?
C18 N3 1.361(8) . ?
C18 C19 1.411(9) . ?
C19 C20 1.356(10) . ?
C19 H19 0.9500 . ?
C20 C21 1.420(10) . ?
C20 H20 0.9500 . ?
C21 C22 1.370(10) . ?
C21 H21 0.9500 . ?
C22 N3 1.369(9) . ?
C22 H22 0.9500 . ?
C23 O1 1.249(8) . ?
C23 N6 1.316(9) . ?
C23 H23 0.9500 . ?
C24 N6 1.488(9) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 N6 1.460(9) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
Cl1 O5 1.435(6) . ?
Cl1 O3 1.437(8) . ?
Cl1 O2 1.438(6) . ?
Cl1 O4 1.445(7) . ?
Cu1 N1 1.926(5) . ?
Cu1 O1 1.980(5) . ?
Cu1 N3 1.985(6) . ?
Cu1 N2 1.987(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 C2 122.9(7) . . ?
N2 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C3 C2 C1 118.3(7) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C4 C3 C2 119.1(6) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 120.2(6) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N2 C5 C4 120.0(6) . . ?
N2 C5 C6 120.3(6) . . ?
C4 C5 C6 119.7(6) . . ?
C8 C6 C7 118.8(6) . . ?
C8 C6 C5 127.7(6) . . ?
C7 C6 C5 113.3(6) . . ?
N4 C7 C6 176.8(8) . . ?
C6 C8 N1 124.7(6) . . ?
C6 C8 C9 127.5(6) . . ?
N1 C8 C9 107.8(5) . . ?
C10 C9 C14 121.6(6) . . ?
C10 C9 C8 132.1(6) . . ?
C14 C9 C8 106.3(6) . . ?
C11 C10 C9 118.1(6) . . ?
C11 C10 H10 120.9 . . ?
C9 C10 H10 120.9 . . ?
C10 C11 C12 120.8(7) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C13 121.0(7) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 118.2(6) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
C9 C14 C13 120.1(6) . . ?
C9 C14 C15 107.6(6) . . ?
C13 C14 C15 132.3(6) . . ?
C16 C15 N1 124.6(6) . . ?
C16 C15 C14 128.0(6) . . ?
N1 C15 C14 107.4(5) . . ?
C15 C16 C17 118.1(6) . . ?
C15 C16 C18 129.0(6) . . ?
C17 C16 C18 112.8(6) . . ?
N5 C17 C16 175.4(7) . . ?
N3 C18 C19 119.2(6) . . ?
N3 C18 C16 120.0(6) . . ?
C19 C18 C16 120.8(6) . . ?
C20 C19 C18 121.4(7) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C20 C21 119.3(6) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C22 C21 C20 117.4(7) . . ?
C22 C21 H21 121.3 . . ?
C20 C21 H21 121.3 . . ?
N3 C22 C21 123.5(7) . . ?
N3 C22 H22 118.3 . . ?
C21 C22 H22 118.3 . . ?
O1 C23 N6 123.6(7) . . ?
O1 C23 H23 118.2 . . ?
N6 C23 H23 118.2 . . ?
N6 C24 H24A 109.5 . . ?
N6 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N6 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N6 C25 H25A 109.5 . . ?
N6 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N6 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O5 Cl1 O3 108.9(5) . . ?
O5 Cl1 O2 110.5(4) . . ?
O3 Cl1 O2 107.9(5) . . ?
O5 Cl1 O4 110.6(5) . . ?
O3 Cl1 O4 109.7(5) . . ?
O2 Cl1 O4 109.3(4) . . ?
N1 Cu1 O1 156.4(2) . . ?
N1 Cu1 N3 95.0(2) . . ?
O1 Cu1 N3 91.9(2) . . ?
N1 Cu1 N2 93.9(2) . . ?
O1 Cu1 N2 88.6(2) . . ?
N3 Cu1 N2 156.2(2) . . ?
C8 N1 C15 110.9(5) . . ?
C8 N1 Cu1 124.1(4) . . ?
C15 N1 Cu1 123.6(4) . . ?
C1 N2 C5 119.2(6) . . ?
C1 N2 Cu1 115.0(5) . . ?
C5 N2 Cu1 125.4(5) . . ?
C18 N3 C22 119.0(6) . . ?
C18 N3 Cu1 125.3(5) . . ?
C22 N3 Cu1 115.5(5) . . ?
C23 N6 C25 121.8(6) . . ?
C23 N6 C24 120.9(6) . . ?
C25 N6 C24 117.2(6) . . ?
C23 O1 Cu1 130.9(5) . . ?

_refine_diff_density_max         3.203
_refine_diff_density_min         -1.162
_refine_diff_density_rms         0.170

