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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1988807'
loop_
_audit_author_name
_audit_author_address
'Briana Schrage'
;The University of Akron
United States of America
;
_audit_update_record             
;
2020-03-06 deposited with the CCDC.	2020-05-21 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            'C11 H9 N5'
_chemical_formula_weight         211.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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                   11.6141(5)
_cell_length_b                   12.7038(5)
_cell_length_c                   13.4922(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.080(3)
_cell_angle_gamma                90
_cell_volume                     1965.74(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3911
_cell_measurement_theta_min      5.20
_cell_measurement_theta_max      67.19

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.046
_exptl_absorpt_coefficient_mu    0.757
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6255
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            6403
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.196
_diffrn_reflns_theta_max         67.330
_diffrn_reflns_theta_full        67.330
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 0.951
_reflns_number_total             1687
_reflns_number_gt                1462
_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)+(0.0934P)²+0.8496P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1687
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1336
_refine_ls_wR_factor_gt          0.1266
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.76680(16) 0.85769(13) 0.07075(13) 0.0226(4) Uani 1 1 d . . . . .
H1 H 0.719414 0.901187 0.023598 0.027 Uiso 1 1 calc R U . . .
C2 C 0.72838(16) 0.81177(14) 0.15307(13) 0.0214(4) Uani 1 1 d . . . . .
H6 H 0.653535 0.817463 0.172593 0.026 Uiso 1 1 calc R U . . .
C3 C 0.82453(16) 0.75543(14) 0.20056(13) 0.0205(4) Uani 1 1 d . . . . .
C4 C 0.77270(15) 0.67100(13) 0.34068(12) 0.0181(4) Uani 1 1 d . . . . .
C5 C 0.79888(16) 0.62936(13) 0.44504(13) 0.0194(4) Uani 1 1 d . . . . .
C6 C 0.69198(15) 0.61578(13) 0.47692(12) 0.0191(4) Uani 1 1 d . . . . .
C7 C 0.68270(16) 0.57706(13) 0.57114(12) 0.0217(4) Uani 1 1 d . . . . .
H5 H 0.609177 0.569242 0.592743 0.026 Uiso 1 1 calc R U . . .
C8 C 0.78645(17) 0.55002(14) 0.63301(13) 0.0246(4) Uani 1 1 d . . . . .
H2 H 0.783604 0.521334 0.697605 0.030 Uiso 1 1 calc R U . . .
C9 C 0.60390(15) 0.64556(13) 0.38942(13) 0.0190(4) Uani 1 1 d . . . . .
C10 C 0.89356(16) 0.56428(14) 0.60185(13) 0.0252(5) Uani 1 1 d . . . . .
H3 H 0.962647 0.545717 0.645935 0.030 Uiso 1 1 calc R U . . .
C11 C 0.90248(16) 0.60532(13) 0.50711(13) 0.0221(4) Uani 1 1 d . . . . .
H4 H 0.975986 0.616206 0.486294 0.027 Uiso 1 1 calc R U . . .
N1 N 0.49084(13) 0.64267(11) 0.38802(11) 0.0213(4) Uani 1 1 d . . . . .
H1A H 0.443237 0.660593 0.333256 0.026 Uiso 1 1 calc R U . . .
H1B H 0.462530 0.622812 0.441838 0.026 Uiso 1 1 calc R U . . .
N2 N 0.65335(13) 0.67489(12) 0.31061(11) 0.0199(4) Uani 1 1 d . . . . .
N3 N 0.85311(13) 0.70120(11) 0.29102(11) 0.0199(4) Uani 1 1 d . . . . .
N4 N 0.91070(14) 0.77071(12) 0.14521(11) 0.0224(4) Uani 1 1 d . . . . .
N5 N 0.87724(14) 0.83409(12) 0.06514(11) 0.0237(4) Uani 1 1 d . . . . .
H7 H 0.992(2) 0.7460(19) 0.1592(17) 0.037(6) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N5 1.331(2) . ?
C1 C2 1.389(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.394(3) . ?
C2 H6 0.9500 . ?
C3 N4 1.354(3) . ?
C3 N3 1.395(2) . ?
C4 N3 1.291(2) . ?
C4 N2 1.382(2) . ?
C4 C5 1.490(2) . ?
C5 C6 1.387(3) . ?
C5 C11 1.387(2) . ?
C6 C7 1.383(2) . ?
C6 C9 1.484(2) . ?
C7 C8 1.396(3) . ?
C7 H5 0.9500 . ?
C8 C10 1.386(3) . ?
C8 H2 0.9500 . ?
C9 N1 1.311(2) . ?
C9 N2 1.339(2) . ?
C10 C11 1.399(3) . ?
C10 H3 0.9500 . ?
C11 H4 0.9500 . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N4 N5 1.354(2) . ?
N4 H7 0.99(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
N5 C1 C2 112.64(16) . . ?
N5 C1 H1 123.7 . . ?
C2 C1 H1 123.7 . . ?
C1 C2 C3 104.36(17) . . ?
C1 C2 H6 127.8 . . ?
C3 C2 H6 127.8 . . ?
N4 C3 C2 106.32(16) . . ?
N4 C3 N3 117.31(15) . . ?
C2 C3 N3 135.91(18) . . ?
N3 C4 N2 127.68(15) . . ?
N3 C4 C5 122.66(15) . . ?
N2 C4 C5 109.62(15) . . ?
C6 C5 C11 121.25(17) . . ?
C6 C5 C4 106.14(14) . . ?
C11 C5 C4 132.61(18) . . ?
C7 C6 C5 122.18(16) . . ?
C7 C6 C9 132.68(17) . . ?
C5 C6 C9 105.06(15) . . ?
C6 C7 C8 116.87(17) . . ?
C6 C7 H5 121.6 . . ?
C8 C7 H5 121.6 . . ?
C10 C8 C7 121.17(17) . . ?
C10 C8 H2 119.4 . . ?
C7 C8 H2 119.4 . . ?
N1 C9 N2 123.42(15) . . ?
N1 C9 C6 124.58(16) . . ?
N2 C9 C6 111.99(15) . . ?
C8 C10 C11 121.67(16) . . ?
C8 C10 H3 119.2 . . ?
C11 C10 H3 119.2 . . ?
C5 C11 C10 116.83(17) . . ?
C5 C11 H4 121.6 . . ?
C10 C11 H4 121.6 . . ?
C9 N1 H1A 120.0 . . ?
C9 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C9 N2 C4 107.04(14) . . ?
C4 N3 C3 120.60(15) . . ?
C3 N4 N5 112.41(15) . . ?
C3 N4 H7 128.3(14) . . ?
N5 N4 H7 119.1(14) . . ?
C1 N5 N4 104.26(15) . . ?

_refine_diff_density_max         0.324
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_Zn(BlzH)(MeOH)2
_database_code_depnum_ccdc_archive 'CCDC 1988811'
loop_
_audit_author_name
_audit_author_address
'Briana Schrage'
;The University of Akron
United States of America
;
_audit_update_record             
;
2020-03-06 deposited with the CCDC.	2020-05-21 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 H21 N9 O2 Zn'
_chemical_formula_weight         532.87

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'
Zn Zn 0.2839 1.4301 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   6.8862(4)
_cell_length_b                   23.1744(14)
_cell_length_c                   14.2313(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.434(4)
_cell_angle_gamma                90
_cell_volume                     2217.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7133
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      28.19

_exptl_crystal_description       needle
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_F_000             1096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.288
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.153
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6892
_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            21335
_diffrn_reflns_av_unetI/netI     0.0772
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.709
_diffrn_reflns_theta_max         28.344
_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             5523
_reflns_number_gt                3745
_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)+(0.0495P)²+1.3705P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5523
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1229
_refine_ls_wR_factor_gt          0.1083
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.9124(5) 0.30214(15) 0.6216(2) 0.0241(8) Uani 1 1 d . . . . .
H1 H 0.957133 0.279347 0.677596 0.029 Uiso 1 1 calc R U . . .
C2 C 1.0189(5) 0.34415(15) 0.5872(2) 0.0219(7) Uani 1 1 d . . . . .
H2 H 1.150965 0.356255 0.614250 0.026 Uiso 1 1 calc R U . . .
C3 C 0.8932(4) 0.36539(14) 0.5044(2) 0.0161(7) Uani 1 1 d . . . . .
C4 C 0.8201(4) 0.42838(14) 0.3696(2) 0.0146(6) Uani 1 1 d . . . . .
C5 C 0.8723(4) 0.47536(13) 0.3102(2) 0.0151(6) Uani 1 1 d . . . . .
C6 C 1.0415(5) 0.50873(14) 0.3185(2) 0.0190(7) Uani 1 1 d . . . . .
H6 H 1.155069 0.502502 0.368699 0.023 Uiso 1 1 calc R U . . .
C7 C 1.0380(5) 0.55184(15) 0.2501(2) 0.0231(7) Uani 1 1 d . . . . .
H7 H 1.152349 0.575356 0.253645 0.028 Uiso 1 1 calc R U . . .
C8 C 0.8718(5) 0.56148(15) 0.1768(2) 0.0220(7) Uani 1 1 d . . . . .
H8 H 0.873202 0.591835 0.132092 0.026 Uiso 1 1 calc R U . . .
C9 C 0.7028(5) 0.52692(14) 0.1684(2) 0.0203(7) Uani 1 1 d . . . . .
H9 H 0.589618 0.532450 0.117660 0.024 Uiso 1 1 calc R U . . .
C10 C 0.7068(4) 0.48436(13) 0.2367(2) 0.0141(6) Uani 1 1 d . . . . .
C11 C 0.5551(4) 0.44205(13) 0.2513(2) 0.0141(6) Uani 1 1 d . . . . .
C12 C 0.2347(4) 0.40332(13) 0.2026(2) 0.0136(6) Uani 1 1 d . . . . .
C13 C 0.0444(4) 0.40171(13) 0.1321(2) 0.0156(7) Uani 1 1 d . . . . .
C14 C -0.0165(5) 0.43021(14) 0.0465(2) 0.0191(7) Uani 1 1 d . . . . .
H14 H 0.068460 0.456653 0.023871 0.023 Uiso 1 1 calc R U . . .
C15 C -0.2075(5) 0.41896(15) -0.0060(2) 0.0211(7) Uani 1 1 d . . . . .
H15 H -0.254920 0.438345 -0.065318 0.025 Uiso 1 1 calc R U . . .
C16 C -0.3298(5) 0.37987(14) 0.0270(2) 0.0207(7) Uani 1 1 d . . . . .
H16 H -0.460106 0.373181 -0.009909 0.025 Uiso 1 1 calc R U . . .
C17 C -0.2654(5) 0.35023(14) 0.1130(2) 0.0182(7) Uani 1 1 d . . . . .
H17 H -0.349107 0.323337 0.135478 0.022 Uiso 1 1 calc R U . . .
C18 C -0.0747(4) 0.36141(13) 0.1647(2) 0.0144(6) Uani 1 1 d . . . . .
C19 C 0.0481(4) 0.33739(13) 0.2548(2) 0.0135(6) Uani 1 1 d . . . . .
C20 C 0.1083(5) 0.27063(13) 0.3860(2) 0.0163(7) Uani 1 1 d . . . . .
C21 C 0.0533(5) 0.22381(15) 0.4349(2) 0.0239(8) Uani 1 1 d . . . . .
H21 H -0.068615 0.203103 0.420640 0.029 Uiso 1 1 calc R U . . .
C22 C 0.2144(5) 0.21410(15) 0.5086(2) 0.0240(8) Uani 1 1 d . . . . .
H22 H 0.221511 0.184377 0.555161 0.029 Uiso 1 1 calc R U . . .
C23 C 0.5155(6) 0.22070(15) 0.2833(3) 0.0308(9) Uani 1 1 d . . . . .
H23A H 0.543122 0.203557 0.347715 0.046 Uiso 1 1 calc R U . . .
H23B H 0.587099 0.199219 0.242008 0.046 Uiso 1 1 calc R U . . .
H23C H 0.372315 0.219010 0.255772 0.046 Uiso 1 1 calc R U . . .
C24 C 0.4473(5) 0.43556(18) 0.5673(2) 0.0338(9) Uani 1 1 d . . . . .
H24A H 0.418269 0.407112 0.613373 0.051 Uiso 1 1 calc R U . . .
H24B H 0.397072 0.473433 0.581477 0.051 Uiso 1 1 calc R U . . .
H24C H 0.591379 0.437796 0.572607 0.051 Uiso 1 1 calc R U . . .
H25 H 0.232(6) 0.4183(16) 0.472(2) 0.027(11) Uiso 1 1 d . . . . .
H26 H 0.704(6) 0.2798(17) 0.295(3) 0.035(12) Uiso 1 1 d . . . . .
N1 N 0.7336(4) 0.29918(12) 0.56172(18) 0.0208(6) Uani 1 1 d . . . . .
H1A H 0.638428 0.275291 0.568819 0.025 Uiso 1 1 calc R U . . .
N2 N 0.7181(4) 0.33730(12) 0.48956(17) 0.0176(6) Uani 1 1 d . . . . .
N3 N 0.9414(4) 0.40936(11) 0.44637(17) 0.0162(6) Uani 1 1 d . . . . .
N4 N 0.6267(4) 0.40999(11) 0.33017(17) 0.0138(5) Uani 1 1 d . . . . .
N5 N 0.3789(4) 0.43988(11) 0.19098(17) 0.0153(6) Uani 1 1 d . . . . .
N6 N 0.2326(4) 0.36546(11) 0.27307(17) 0.0148(5) Uani 1 1 d . . . . .
N7 N -0.0096(4) 0.29606(11) 0.30426(17) 0.0154(6) Uani 1 1 d . . . . .
N8 N 0.2952(4) 0.28753(11) 0.42934(17) 0.0170(6) Uani 1 1 d . . . . .
N9 N 0.3612(4) 0.25211(12) 0.50639(18) 0.0226(6) Uani 1 1 d . . . . .
O1 O 0.5785(4) 0.27858(10) 0.28940(17) 0.0248(6) Uani 1 1 d . . . . .
O2 O 0.3537(4) 0.41873(11) 0.47277(16) 0.0224(5) Uani 1 1 d . . . . .
Zn1 Zn 0.46519(5) 0.34834(2) 0.38473(3) 0.01848(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 1.340(4) . ?
C1 C2 1.371(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.394(4) . ?
C2 H2 0.9500 . ?
C3 N2 1.346(4) . ?
C3 N3 1.396(4) . ?
C4 N3 1.301(4) . ?
C4 N4 1.396(4) . ?
C4 C5 1.470(4) . ?
C5 C6 1.382(4) . ?
C5 C10 1.386(4) . ?
C6 C7 1.391(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.391(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.396(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.479(4) . ?
C11 N5 1.328(4) . ?
C11 N4 1.348(4) . ?
C12 N6 1.335(4) . ?
C12 N5 1.343(4) . ?
C12 C13 1.469(4) . ?
C13 C14 1.369(4) . ?
C13 C18 1.388(4) . ?
C14 C15 1.391(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.484(4) . ?
C19 N7 1.300(4) . ?
C19 N6 1.401(4) . ?
C20 N8 1.360(4) . ?
C20 C21 1.386(4) . ?
C20 N7 1.397(4) . ?
C21 C22 1.371(5) . ?
C21 H21 0.9500 . ?
C22 N9 1.346(4) . ?
C22 H22 0.9500 . ?
C23 O1 1.407(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 O2 1.416(4) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
N1 N2 1.341(3) . ?
N1 H1A 0.8800 . ?
N2 Zn1 2.051(2) . ?
N4 Zn1 2.062(3) . ?
N6 Zn1 2.037(2) . ?
N8 N9 1.367(3) . ?
N8 Zn1 2.020(3) . ?
O1 Zn1 2.349(2) . ?
O1 H26 0.85(4) . ?
O2 Zn1 2.288(2) . ?
O2 H25 0.84(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
N1 C1 C2 107.3(3) . . ?
N1 C1 H1 126.3 . . ?
C2 C1 H1 126.3 . . ?
C1 C2 C3 105.7(3) . . ?
C1 C2 H2 127.2 . . ?
C3 C2 H2 127.2 . . ?
N2 C3 C2 109.5(3) . . ?
N2 C3 N3 125.4(3) . . ?
C2 C3 N3 125.1(3) . . ?
N3 C4 N4 128.2(3) . . ?
N3 C4 C5 122.8(3) . . ?
N4 C4 C5 109.0(2) . . ?
C6 C5 C10 121.4(3) . . ?
C6 C5 C4 132.2(3) . . ?
C10 C5 C4 106.4(3) . . ?
C5 C6 C7 117.0(3) . . ?
C5 C6 H6 121.5 . . ?
C7 C6 H6 121.5 . . ?
C8 C7 C6 121.8(3) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C9 120.5(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 117.3(3) . . ?
C10 C9 H9 121.3 . . ?
C8 C9 H9 121.3 . . ?
C9 C10 C5 121.8(3) . . ?
C9 C10 C11 131.6(3) . . ?
C5 C10 C11 106.6(3) . . ?
N5 C11 N4 129.6(3) . . ?
N5 C11 C10 120.6(3) . . ?
N4 C11 C10 109.9(2) . . ?
N6 C12 N5 129.4(3) . . ?
N6 C12 C13 110.2(3) . . ?
N5 C12 C13 120.4(3) . . ?
C14 C13 C18 122.2(3) . . ?
C14 C13 C12 130.8(3) . . ?
C18 C13 C12 107.0(3) . . ?
C13 C14 C15 117.4(3) . . ?
C13 C14 H14 121.3 . . ?
C15 C14 H14 121.3 . . ?
C16 C15 C14 120.9(3) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 121.3(3) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 117.5(3) . . ?
C18 C17 H17 121.3 . . ?
C16 C17 H17 121.3 . . ?
C17 C18 C13 120.6(3) . . ?
C17 C18 C19 133.5(3) . . ?
C13 C18 C19 105.9(3) . . ?
N7 C19 N6 127.7(3) . . ?
N7 C19 C18 124.1(3) . . ?
N6 C19 C18 108.1(3) . . ?
N8 C20 C21 109.4(3) . . ?
N8 C20 N7 125.4(3) . . ?
C21 C20 N7 125.2(3) . . ?
C22 C21 C20 104.4(3) . . ?
C22 C21 H21 127.8 . . ?
C20 C21 H21 127.8 . . ?
N9 C22 C21 111.3(3) . . ?
N9 C22 H22 124.4 . . ?
C21 C22 H22 124.4 . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1 N1 N2 111.3(3) . . ?
C1 N1 H1A 124.3 . . ?
N2 N1 H1A 124.3 . . ?
N1 N2 C3 106.1(2) . . ?
N1 N2 Zn1 123.6(2) . . ?
C3 N2 Zn1 130.2(2) . . ?
C4 N3 C3 123.5(3) . . ?
C11 N4 C4 108.2(2) . . ?
C11 N4 Zn1 124.4(2) . . ?
C4 N4 Zn1 127.25(19) . . ?
C11 N5 C12 122.8(3) . . ?
C12 N6 C19 108.8(2) . . ?
C12 N6 Zn1 125.5(2) . . ?
C19 N6 Zn1 125.7(2) . . ?
C19 N7 C20 124.8(3) . . ?
C20 N8 N9 108.0(2) . . ?
C20 N8 Zn1 127.9(2) . . ?
N9 N8 Zn1 123.8(2) . . ?
C22 N9 N8 106.9(3) . . ?
C23 O1 Zn1 123.8(2) . . ?
C23 O1 H26 109(3) . . ?
Zn1 O1 H26 112(3) . . ?
C24 O2 Zn1 125.4(2) . . ?
C24 O2 H25 105(2) . . ?
Zn1 O2 H25 116(3) . . ?
N8 Zn1 N6 88.26(10) . . ?
N8 Zn1 N2 98.23(10) . . ?
N6 Zn1 N2 173.44(10) . . ?
N8 Zn1 N4 176.19(10) . . ?
N6 Zn1 N4 88.19(10) . . ?
N2 Zn1 N4 85.29(10) . . ?
N8 Zn1 O2 92.29(10) . . ?
N6 Zn1 O2 89.32(9) . . ?
N2 Zn1 O2 91.32(9) . . ?
N4 Zn1 O2 89.08(9) . . ?
N8 Zn1 O1 89.34(10) . . ?
N6 Zn1 O1 89.24(9) . . ?
N2 Zn1 O1 89.92(10) . . ?
N4 Zn1 O1 89.21(9) . . ?
O2 Zn1 O1 177.80(8) . . ?

_refine_diff_density_max         1.555
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.100

####################################################################### 
# 
# 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_H2BlzH
_database_code_depnum_ccdc_archive 'CCDC 1988808'
loop_
_audit_author_name
_audit_author_address
'Briana Schrage'
;The University of Akron
United States of America
;
_audit_update_record             
;
2020-03-06 deposited with the CCDC.	2020-05-21 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            'C22 H15 N9'
_chemical_formula_weight         405.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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                   4.579(6)
_cell_length_b                   17.112(13)
_cell_length_c                   23.460(16)
_cell_angle_alpha                90
_cell_angle_beta                 93.02(8)
_cell_angle_gamma                90
_cell_volume                     1836(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2923
_cell_measurement_theta_min      4.58
_cell_measurement_theta_max      67.18

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.415
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.079
_exptl_absorpt_coefficient_mu    0.772
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5655
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            11216
_diffrn_reflns_av_unetI/netI     0.0815
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.198
_diffrn_reflns_theta_max         67.428
_diffrn_reflns_theta_full        67.428
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 0.941
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 0.941
_reflns_number_total             3125
_reflns_number_gt                1977
_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)+(0.1101P)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         3125
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1127
_refine_ls_R_factor_gt           0.0674
_refine_ls_wR_factor_ref         0.1976
_refine_ls_wR_factor_gt          0.1725
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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 1.1566(9) 0.5560(2) 0.57847(17) 0.0433(11) Uani 1 1 d . . . . .
H1 H 1.296599 0.516436 0.572028 0.052 Uiso 1 1 calc R U . . .
C2 C 0.9976(9) 0.5962(2) 0.53614(17) 0.0378(10) Uani 1 1 d . . . . .
H2 H 1.006328 0.589502 0.496058 0.045 Uiso 1 1 calc R U . . .
C3 C 0.8225(8) 0.6483(2) 0.56433(17) 0.0356(9) Uani 1 1 d . . . . .
C4 C 0.4744(8) 0.7485(2) 0.56690(16) 0.0323(9) Uani 1 1 d . . . . .
C5 C 0.2702(8) 0.8049(2) 0.53915(15) 0.0318(9) Uani 1 1 d . . . . .
C6 C 0.1954(8) 0.8208(2) 0.48234(16) 0.0343(9) Uani 1 1 d . . . . .
H6 H 0.286021 0.794234 0.452420 0.041 Uiso 1 1 calc R U . . .
C7 C -0.0175(9) 0.8773(2) 0.47100(17) 0.0371(10) Uani 1 1 d . . . . .
H7 H -0.075917 0.889210 0.432524 0.045 Uiso 1 1 calc R U . . .
C8 C -0.1467(9) 0.9167(2) 0.51491(16) 0.0384(10) Uani 1 1 d . . . . .
H8 H -0.291287 0.955127 0.505782 0.046 Uiso 1 1 calc R U . . .
C9 C -0.0699(9) 0.9012(2) 0.57166(16) 0.0362(9) Uani 1 1 d . . . . .
H9 H -0.158121 0.928413 0.601588 0.043 Uiso 1 1 calc R U . . .
C10 C 0.1402(9) 0.8447(2) 0.58290(16) 0.0342(9) Uani 1 1 d . . . . .
C11 C 0.2633(8) 0.8121(2) 0.63654(16) 0.0338(9) Uani 1 1 d . . . . .
C12 C 0.2557(8) 0.8071(2) 0.73626(16) 0.0341(9) Uani 1 1 d . . . . .
C13 C 0.1385(8) 0.8357(2) 0.79004(16) 0.0339(9) Uani 1 1 d . . . . .
C14 C -0.0611(9) 0.8948(2) 0.79982(16) 0.0367(9) Uani 1 1 d . . . . .
H14 H -0.144770 0.925702 0.769533 0.044 Uiso 1 1 calc R U . . .
C15 C -0.1321(9) 0.9064(2) 0.85574(16) 0.0375(10) Uani 1 1 d . . . . .
H15 H -0.267977 0.946227 0.864194 0.045 Uiso 1 1 calc R U . . .
C16 C -0.0074(9) 0.8606(2) 0.90024(17) 0.0385(10) Uani 1 1 d . . . . .
H16 H -0.061355 0.869690 0.938228 0.046 Uiso 1 1 calc R U . . .
C17 C 0.1921(9) 0.8027(2) 0.88986(16) 0.0367(9) Uani 1 1 d . . . . .
H17 H 0.279263 0.772263 0.920072 0.044 Uiso 1 1 calc R U . . .
C18 C 0.2610(8) 0.7904(2) 0.83368(16) 0.0328(9) Uani 1 1 d . . . . .
C19 C 0.4609(8) 0.7333(2) 0.80766(15) 0.0311(9) Uani 1 1 d . . . . .
C20 C 0.7954(8) 0.6293(2) 0.81065(17) 0.0352(9) Uani 1 1 d . . . . .
C21 C 0.9477(9) 0.5701(2) 0.83992(17) 0.0360(9) Uani 1 1 d . . . . .
H21 H 0.945736 0.557918 0.879407 0.043 Uiso 1 1 calc R U . . .
C22 C 1.1027(9) 0.5328(2) 0.79876(16) 0.0383(10) Uani 1 1 d . . . . .
H22 H 1.229851 0.489431 0.805109 0.046 Uiso 1 1 calc R U . . .
N1 N 1.0838(7) 0.58121(18) 0.62999(14) 0.0385(8) Uani 1 1 d . . . . .
N2 N 0.8791(8) 0.63773(18) 0.62122(15) 0.0403(9) Uani 1 1 d . . . . .
H2A H 0.795435 0.663717 0.648314 0.048 Uiso 1 1 calc R U . . .
N3 N 0.6339(7) 0.70118(18) 0.53868(13) 0.0349(8) Uani 1 1 d . . . . .
N4 N 0.4626(7) 0.75628(17) 0.62709(13) 0.0323(7) Uani 1 1 d . . . . .
N5 N 0.1695(7) 0.83878(18) 0.68648(13) 0.0355(8) Uani 1 1 d . . . . .
N6 N 0.4434(7) 0.74796(17) 0.74809(13) 0.0350(8) Uani 1 1 d . . . . .
H6A H 0.540550 0.722275 0.722674 0.042 Uiso 1 1 calc R U . . .
N7 N 0.6087(7) 0.68198(17) 0.83568(13) 0.0350(8) Uani 1 1 d . . . . .
N8 N 0.8514(7) 0.62732(18) 0.75457(14) 0.0374(8) Uani 1 1 d . . . . .
N9 N 1.0437(7) 0.56785(19) 0.74869(14) 0.0408(9) Uani 1 1 d . . . . .
H9A H 1.118907 0.554323 0.716378 0.049 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.342(5) . ?
C1 C2 1.383(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.390(5) . ?
C2 H2 0.9500 . ?
C3 N2 1.358(5) . ?
C3 N3 1.368(5) . ?
C4 N3 1.295(5) . ?
C4 N4 1.422(5) . ?
C4 C5 1.472(5) . ?
C5 C6 1.385(6) . ?
C5 C10 1.392(5) . ?
C6 C7 1.388(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.462(6) . ?
C11 N4 1.348(5) . ?
C11 N5 1.348(5) . ?
C12 N5 1.328(5) . ?
C12 N6 1.347(5) . ?
C12 C13 1.480(5) . ?
C13 C18 1.380(6) . ?
C13 C14 1.390(5) . ?
C14 C15 1.382(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.403(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.491(5) . ?
C19 N7 1.271(5) . ?
C19 N6 1.418(5) . ?
C20 N8 1.354(5) . ?
C20 C21 1.391(6) . ?
C20 N7 1.393(5) . ?
C21 C22 1.384(5) . ?
C21 H21 0.9500 . ?
C22 N9 1.334(5) . ?
C22 H22 0.9500 . ?
N1 N2 1.355(5) . ?
N2 H2A 0.8800 . ?
N6 H6A 0.8800 . ?
N8 N9 1.357(4) . ?
N9 H9A 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
N1 C1 C2 109.9(3) . . ?
N1 C1 H1 125.0 . . ?
C2 C1 H1 125.0 . . ?
C1 C2 C3 105.8(4) . . ?
C1 C2 H2 127.1 . . ?
C3 C2 H2 127.1 . . ?
N2 C3 N3 127.1(3) . . ?
N2 C3 C2 107.3(4) . . ?
N3 C3 C2 125.6(4) . . ?
N3 C4 N4 128.2(4) . . ?
N3 C4 C5 123.1(3) . . ?
N4 C4 C5 108.7(3) . . ?
C6 C5 C10 121.3(4) . . ?
C6 C5 C4 132.3(3) . . ?
C10 C5 C4 106.3(3) . . ?
C5 C6 C7 117.2(3) . . ?
C5 C6 H6 121.4 . . ?
C7 C6 H6 121.4 . . ?
C6 C7 C8 121.2(4) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C7 121.6(4) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C10 C9 C8 117.2(3) . . ?
C10 C9 H9 121.4 . . ?
C8 C9 H9 121.4 . . ?
C9 C10 C5 121.5(4) . . ?
C9 C10 C11 131.7(3) . . ?
C5 C10 C11 106.7(4) . . ?
N4 C11 N5 129.2(4) . . ?
N4 C11 C10 111.3(3) . . ?
N5 C11 C10 119.5(3) . . ?
N5 C12 N6 130.1(3) . . ?
N5 C12 C13 120.7(3) . . ?
N6 C12 C13 109.2(3) . . ?
C18 C13 C14 122.1(3) . . ?
C18 C13 C12 107.2(3) . . ?
C14 C13 C12 130.7(4) . . ?
C15 C14 C13 116.8(4) . . ?
C15 C14 H14 121.6 . . ?
C13 C14 H14 121.6 . . ?
C14 C15 C16 121.2(4) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 121.2(3) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 117.6(4) . . ?
C16 C17 H17 121.2 . . ?
C18 C17 H17 121.2 . . ?
C13 C18 C17 121.1(3) . . ?
C13 C18 C19 107.4(3) . . ?
C17 C18 C19 131.6(4) . . ?
N7 C19 N6 129.2(3) . . ?
N7 C19 C18 124.2(3) . . ?
N6 C19 C18 106.5(3) . . ?
N8 C20 C21 110.2(3) . . ?
N8 C20 N7 125.3(4) . . ?
C21 C20 N7 124.5(4) . . ?
C22 C21 C20 104.7(4) . . ?
C22 C21 H21 127.7 . . ?
C20 C21 H21 127.7 . . ?
N9 C22 C21 108.6(4) . . ?
N9 C22 H22 125.7 . . ?
C21 C22 H22 125.7 . . ?
C1 N1 N2 107.2(3) . . ?
N1 N2 C3 109.8(3) . . ?
N1 N2 H2A 125.1 . . ?
C3 N2 H2A 125.1 . . ?
C4 N3 C3 123.2(4) . . ?
C11 N4 C4 106.9(3) . . ?
C12 N5 C11 122.2(3) . . ?
C12 N6 C19 109.7(3) . . ?
C12 N6 H6A 125.1 . . ?
C19 N6 H6A 125.1 . . ?
C19 N7 C20 123.4(3) . . ?
C20 N8 N9 105.9(3) . . ?
C22 N9 N8 110.5(3) . . ?
C22 N9 H9A 124.8 . . ?
N8 N9 H9A 124.8 . . ?

_refine_diff_density_max         0.367
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_Co(BlzH)(MeOH)2
_database_code_depnum_ccdc_archive 'CCDC 1988809'
loop_
_audit_author_name
_audit_author_address
'Briana Schrage'
;The University of Akron
United States of America
;
_audit_update_record             
;
2020-03-06 deposited with the CCDC.	2020-05-21 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 H21 Co N9 O2'
_chemical_formula_weight         526.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   6.8635(3)
_cell_length_b                   23.0498(13)
_cell_length_c                   14.1576(8)
_cell_angle_alpha                90
_cell_angle_beta                 102.251(3)
_cell_angle_gamma                90
_cell_volume                     2188.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6022
_cell_measurement_theta_min      3.73
_cell_measurement_theta_max      66.64

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_F_000             1084
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.587
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.066
_exptl_absorpt_coefficient_mu    6.531
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5108
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            11209
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.726
_diffrn_reflns_theta_max         66.631
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_max 0.860
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_Laue_measured_fraction_full 0.860
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_point_group_measured_fraction_full 0.860
_reflns_number_total             3325
_reflns_number_gt                2784
_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)+(0.0689P)²+0.9247P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3325
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1228
_refine_ls_wR_factor_gt          0.1159
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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 0.7744(5) 0.21809(16) 0.4864(3) 0.0259(8) Uani 1 1 d . . . . .
H1 H 0.763332 0.189751 0.436797 0.031 Uiso 1 1 calc R U . . .
C2 C 0.9380(5) 0.22587(15) 0.5596(2) 0.0233(8) Uani 1 1 d . . . . .
H2 H 1.059385 0.204631 0.571445 0.028 Uiso 1 1 calc R U . . .
C3 C 0.8853(5) 0.27252(15) 0.6133(2) 0.0212(8) Uani 1 1 d . . . . .
C4 C 0.9461(5) 0.33657(15) 0.7436(2) 0.0191(8) Uani 1 1 d . . . . .
C5 C 1.0697(5) 0.36005(15) 0.8337(3) 0.0199(8) Uani 1 1 d . . . . .
C6 C 1.2620(5) 0.34904(14) 0.8851(2) 0.0216(8) Uani 1 1 d . . . . .
H6 H 1.345452 0.321856 0.862331 0.026 Uiso 1 1 calc R U . . .
C7 C 1.3280(5) 0.37909(15) 0.9707(3) 0.0239(8) Uani 1 1 d . . . . .
H7 H 1.459930 0.372796 1.006414 0.029 Uiso 1 1 calc R U . . .
C8 C 1.2056(5) 0.41838(16) 1.0057(2) 0.0242(8) Uani 1 1 d . . . . .
H8 H 1.253766 0.437604 1.065467 0.029 Uiso 1 1 calc R U . . .
C9 C 1.0139(5) 0.42952(15) 0.9538(2) 0.0219(8) Uani 1 1 d . . . . .
H9 H 0.929394 0.456289 0.976707 0.026 Uiso 1 1 calc R U . . .
C10 C 0.9506(5) 0.40046(14) 0.8680(2) 0.0192(8) Uani 1 1 d . . . . .
C11 C 0.7611(5) 0.40235(14) 0.7978(2) 0.0181(7) Uani 1 1 d . . . . .
C12 C 0.4455(5) 0.44127(14) 0.7488(2) 0.0197(7) Uani 1 1 d . . . . .
C13 C 0.2949(5) 0.48375(15) 0.7634(3) 0.0205(8) Uani 1 1 d . . . . .
C14 C 0.2983(5) 0.52702(15) 0.8315(3) 0.0235(8) Uani 1 1 d . . . . .
H14 H 0.411646 0.533057 0.882172 0.028 Uiso 1 1 calc R U . . .
C15 C 0.1278(5) 0.56144(16) 0.8225(3) 0.0249(8) Uani 1 1 d . . . . .
H15 H 0.125110 0.592027 0.867148 0.030 Uiso 1 1 calc R U . . .
C16 C -0.0388(5) 0.55133(15) 0.7483(3) 0.0244(8) Uani 1 1 d . . . . .
H16 H -0.153513 0.575049 0.744078 0.029 Uiso 1 1 calc R U . . .
C17 C -0.0410(5) 0.50785(15) 0.6813(3) 0.0236(8) Uani 1 1 d . . . . .
H17 H -0.155101 0.501074 0.631346 0.028 Uiso 1 1 calc R U . . .
C18 C 0.1306(5) 0.47419(14) 0.6895(2) 0.0192(7) Uani 1 1 d . . . . .
C19 C 0.1843(5) 0.42713(14) 0.6303(2) 0.0185(7) Uani 1 1 d . . . . .
C20 C 0.1199(5) 0.36464(15) 0.4980(2) 0.0197(7) Uani 1 1 d . . . . .
C21 C 0.0000(5) 0.34313(14) 0.4132(3) 0.0230(8) Uani 1 1 d . . . . .
H21 H -0.131898 0.354703 0.384171 0.028 Uiso 1 1 calc R U . . .
C22 C 0.1127(5) 0.30197(16) 0.3810(3) 0.0252(8) Uani 1 1 d . . . . .
H22 H 0.073056 0.279470 0.323956 0.030 Uiso 1 1 calc R U . . .
C23 C 0.5549(5) 0.43330(18) 0.4335(3) 0.0338(9) Uani 1 1 d . . . . .
H23A H 0.562381 0.399716 0.392016 0.051 Uiso 1 1 calc R U . . .
H23B H 0.622725 0.466407 0.411287 0.051 Uiso 1 1 calc R U . . .
H23C H 0.414858 0.443191 0.430534 0.051 Uiso 1 1 calc R U . . .
C24 C 0.4830(5) 0.21887(16) 0.7126(3) 0.0313(9) Uani 1 1 d . . . . .
H24A H 0.439550 0.203875 0.646686 0.047 Uiso 1 1 calc R U . . .
H24B H 0.421077 0.196079 0.756766 0.047 Uiso 1 1 calc R U . . .
H24C H 0.628357 0.215930 0.732375 0.047 Uiso 1 1 calc R U . . .
Co1 Co 0.53380(7) 0.34940(2) 0.61967(4) 0.0186(2) Uani 1 1 d . . . . .
N1 N 0.6314(4) 0.25653(13) 0.4950(2) 0.0251(7) Uani 1 1 d . . . . .
N2 N 0.6965(4) 0.29025(12) 0.5733(2) 0.0203(6) Uani 1 1 d . . . . .
N3 N 1.0051(4) 0.29564(12) 0.6942(2) 0.0209(6) Uani 1 1 d . . . . .
N4 N 0.7585(4) 0.36402(12) 0.7251(2) 0.0194(6) Uani 1 1 d . . . . .
N5 N 0.6209(4) 0.43936(12) 0.81168(19) 0.0200(6) Uani 1 1 d . . . . .
N6 N 0.3805(4) 0.40844(12) 0.6702(2) 0.0200(6) Uani 1 1 d . . . . .
N7 N 0.0648(4) 0.40789(12) 0.5541(2) 0.0198(6) Uani 1 1 d . . . . .
N8 N 0.2983(4) 0.33713(12) 0.5164(2) 0.0209(6) Uani 1 1 d . . . . .
N9 N 0.2884(4) 0.29856(12) 0.4432(2) 0.0224(7) Uani 1 1 d . . . . .
H9A H 0.384842 0.274524 0.437402 0.027 Uiso 1 1 calc R U . . .
O1 O 0.6487(4) 0.41969(11) 0.53024(17) 0.0249(6) Uani 1 1 d . . . . .
O2 O 0.4243(4) 0.27833(10) 0.71535(18) 0.0249(6) Uani 1 1 d . . . . .
H25 H 0.296(8) 0.280(2) 0.709(4) 0.072(17) Uiso 1 1 d . . . . .
H26 H 0.769(8) 0.417(2) 0.537(4) 0.072(18) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.347(4) . ?
C1 C2 1.369(5) . ?
C2 C3 1.408(5) . ?
C3 N2 1.362(4) . ?
C3 N3 1.369(4) . ?
C4 N3 1.290(4) . ?
C4 N4 1.408(4) . ?
C4 C5 1.476(5) . ?
C5 C6 1.389(5) . ?
C5 C10 1.393(5) . ?
C6 C7 1.386(5) . ?
C7 C8 1.396(5) . ?
C8 C9 1.389(5) . ?
C9 C10 1.374(5) . ?
C10 C11 1.460(5) . ?
C11 N5 1.331(4) . ?
C11 N4 1.354(4) . ?
C12 N5 1.338(4) . ?
C12 N6 1.342(4) . ?
C12 C13 1.470(5) . ?
C13 C14 1.383(5) . ?
C13 C18 1.384(5) . ?
C14 C15 1.397(5) . ?
C15 C16 1.398(5) . ?
C16 C17 1.378(5) . ?
C17 C18 1.394(5) . ?
C18 C19 1.465(5) . ?
C19 N7 1.288(4) . ?
C19 N6 1.412(4) . ?
C20 N8 1.354(4) . ?
C20 N7 1.376(4) . ?
C20 C21 1.395(5) . ?
C21 C22 1.362(5) . ?
C22 N9 1.336(4) . ?
C23 O1 1.419(4) . ?
C24 O2 1.431(4) . ?
Co1 N4 1.935(3) . ?
Co1 N6 1.947(3) . ?
Co1 N8 1.956(3) . ?
Co1 N2 1.961(3) . ?
Co1 O1 2.296(3) . ?
Co1 O2 2.348(3) . ?
N1 N2 1.351(4) . ?
N8 N9 1.357(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
N1 C1 C2 110.0(3) . . ?
C1 C2 C3 104.2(3) . . ?
N2 C3 N3 125.5(3) . . ?
N2 C3 C2 109.6(3) . . ?
N3 C3 C2 124.9(3) . . ?
N3 C4 N4 127.4(3) . . ?
N3 C4 C5 123.2(3) . . ?
N4 C4 C5 109.4(3) . . ?
C6 C5 C10 120.2(3) . . ?
C6 C5 C4 133.9(3) . . ?
C10 C5 C4 105.9(3) . . ?
C7 C6 C5 117.7(3) . . ?
C6 C7 C8 121.7(3) . . ?
C9 C8 C7 120.4(3) . . ?
C10 C9 C8 117.7(3) . . ?
C9 C10 C5 122.3(3) . . ?
C9 C10 C11 130.9(3) . . ?
C5 C10 C11 106.7(3) . . ?
N5 C11 N4 129.6(3) . . ?
N5 C11 C10 119.1(3) . . ?
N4 C11 C10 111.3(3) . . ?
N5 C12 N6 128.9(3) . . ?
N5 C12 C13 119.3(3) . . ?
N6 C12 C13 111.9(3) . . ?
C14 C13 C18 122.2(3) . . ?
C14 C13 C12 132.1(3) . . ?
C18 C13 C12 105.8(3) . . ?
C13 C14 C15 117.1(3) . . ?
C14 C15 C16 120.7(3) . . ?
C17 C16 C15 121.7(3) . . ?
C16 C17 C18 117.5(3) . . ?
C13 C18 C17 120.9(3) . . ?
C13 C18 C19 106.7(3) . . ?
C17 C18 C19 132.4(3) . . ?
N7 C19 N6 127.9(3) . . ?
N7 C19 C18 122.8(3) . . ?
N6 C19 C18 109.4(3) . . ?
N8 C20 N7 125.2(3) . . ?
N8 C20 C21 110.1(3) . . ?
N7 C20 C21 124.7(3) . . ?
C22 C21 C20 105.2(3) . . ?
N9 C22 C21 108.5(3) . . ?
N4 Co1 N6 89.97(11) . . ?
N4 Co1 N8 177.07(12) . . ?
N6 Co1 N8 87.14(11) . . ?
N4 Co1 N2 87.81(11) . . ?
N6 Co1 N2 177.76(11) . . ?
N8 Co1 N2 95.07(11) . . ?
N4 Co1 O1 89.52(10) . . ?
N6 Co1 O1 89.13(11) . . ?
N8 Co1 O1 90.92(11) . . ?
N2 Co1 O1 91.12(10) . . ?
N4 Co1 O2 88.67(10) . . ?
N6 Co1 O2 90.68(10) . . ?
N8 Co1 O2 90.88(10) . . ?
N2 Co1 O2 89.00(10) . . ?
O1 Co1 O2 178.18(9) . . ?
C1 N1 N2 109.4(3) . . ?
N1 N2 C3 106.7(3) . . ?
N1 N2 Co1 124.2(2) . . ?
C3 N2 Co1 129.0(2) . . ?
C4 N3 C3 122.4(3) . . ?
C11 N4 C4 106.7(3) . . ?
C11 N4 Co1 125.4(2) . . ?
C4 N4 Co1 127.8(2) . . ?
C11 N5 C12 120.0(3) . . ?
C12 N6 C19 106.3(3) . . ?
C12 N6 Co1 126.1(2) . . ?
C19 N6 Co1 127.6(2) . . ?
C19 N7 C20 121.9(3) . . ?
C20 N8 N9 105.3(3) . . ?
C20 N8 Co1 130.2(2) . . ?
N9 N8 Co1 124.4(2) . . ?
C22 N9 N8 110.9(3) . . ?
C23 O1 Co1 123.3(2) . . ?
C24 O2 Co1 121.7(2) . . ?

_refine_diff_density_max         0.532
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_Cu(BlzH)
_database_code_depnum_ccdc_archive 'CCDC 1988810'
loop_
_audit_author_name
_audit_author_address
'Briana Schrage'
;The University of Akron
United States of America
;
_audit_update_record             
;
2020-03-06 deposited with the CCDC.	2020-05-21 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            'C22 H13 Cu N9'
_chemical_formula_weight         466.95

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   4.6467(4)
_cell_length_b                   16.7271(17)
_cell_length_c                   23.289(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.885(7)
_cell_angle_gamma                90
_cell_volume                     1807.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3183
_cell_measurement_theta_min      3.25
_cell_measurement_theta_max      66.55

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_F_000             948
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.134
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.042
_exptl_absorpt_coefficient_mu    1.994
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6580
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            8721
_diffrn_reflns_av_unetI/netI     0.0665
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.254
_diffrn_reflns_theta_max         67.455
_diffrn_reflns_theta_full        'ACTA 50'
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measured_fraction_theta_full 'ACTA 50'
_diffrn_reflns_Laue_measured_fraction_max 0.881
_diffrn_reflns_Laue_measured_fraction_full 0.881
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_point_group_measured_fraction_full 0.881
_reflns_number_total             2876
_reflns_number_gt                1916
_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)+(0.0858P)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         2876
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1454
_refine_ls_wR_factor_gt          0.1239
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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 -0.1045(10) 0.5362(3) 0.20657(19) 0.0260(11) Uani 1 1 d . . . . .
H1 H -0.237969 0.493643 0.200488 0.031 Uiso 1 1 calc R U . . .
C2 C 0.0479(9) 0.5722(3) 0.16523(19) 0.0242(11) Uani 1 1 d . . . . .
H2 H 0.044020 0.559677 0.125409 0.029 Uiso 1 1 calc R U . . .
C3 C 0.2101(9) 0.6312(3) 0.19385(19) 0.0241(11) Uani 1 1 d . . . . .
C4 C 0.5442(9) 0.7347(3) 0.19593(18) 0.0224(11) Uani 1 1 d . . . . .
C5 C 0.7416(9) 0.7912(3) 0.16908(18) 0.0214(11) Uani 1 1 d . . . . .
C6 C 0.8066(9) 0.8032(3) 0.11201(19) 0.0226(11) Uani 1 1 d . . . . .
H6 H 0.717373 0.772620 0.081715 0.027 Uiso 1 1 calc R U . . .
C7 C 1.0078(9) 0.8620(3) 0.10147(19) 0.0239(11) Uani 1 1 d . . . . .
H7 H 1.057353 0.871729 0.063011 0.029 Uiso 1 1 calc R U . . .
C8 C 1.1395(9) 0.9071(3) 0.14572(19) 0.0267(11) Uani 1 1 d . . . . .
H8 H 1.276787 0.946722 0.136893 0.032 Uiso 1 1 calc R U . . .
C9 C 1.0732(9) 0.8950(3) 0.20226(19) 0.0229(10) Uani 1 1 d . . . . .
H9 H 1.161688 0.925678 0.232604 0.028 Uiso 1 1 calc R U . . .
C10 C 0.8716(9) 0.8361(3) 0.21285(18) 0.0216(10) Uani 1 1 d . . . . .
C11 C 0.7559(9) 0.8082(3) 0.26678(18) 0.0211(10) Uani 1 1 d . . . . .
C12 C 0.7544(9) 0.8138(3) 0.36599(18) 0.0224(11) Uani 1 1 d . . . . .
C13 C 0.8715(9) 0.8449(3) 0.42051(18) 0.0207(10) Uani 1 1 d . . . . .
C14 C 1.0840(9) 0.9020(3) 0.43306(19) 0.0247(11) Uani 1 1 d . . . . .
H14 H 1.176647 0.929467 0.403446 0.030 Uiso 1 1 calc R U . . .
C15 C 1.1543(9) 0.9168(3) 0.49058(18) 0.0247(11) Uani 1 1 d . . . . .
H15 H 1.300044 0.954916 0.500596 0.030 Uiso 1 1 calc R U . . .
C16 C 1.0164(9) 0.8773(3) 0.53407(19) 0.0253(11) Uani 1 1 d . . . . .
H16 H 1.068322 0.889299 0.573093 0.030 Uiso 1 1 calc R U . . .
C17 C 0.8043(10) 0.8206(3) 0.52144(19) 0.0244(11) Uani 1 1 d . . . . .
H17 H 0.711004 0.793262 0.551053 0.029 Uiso 1 1 calc R U . . .
C18 C 0.7341(9) 0.8054(3) 0.46383(19) 0.0223(11) Uani 1 1 d . . . . .
C19 C 0.5323(9) 0.7490(3) 0.43496(18) 0.0222(10) Uani 1 1 d . . . . .
C20 C 0.1800(9) 0.6500(3) 0.43359(19) 0.0234(11) Uani 1 1 d . . . . .
C21 C -0.0009(9) 0.5979(3) 0.46146(19) 0.0268(11) Uani 1 1 d . . . . .
H21 H -0.014650 0.590493 0.501672 0.032 Uiso 1 1 calc R U . . .
C22 C -0.1561(10) 0.5594(3) 0.41733(19) 0.0265(11) Uani 1 1 d . . . . .
H22 H -0.300066 0.520218 0.422734 0.032 Uiso 1 1 calc R U . . .
Cu1 Cu 0.34773(13) 0.69319(4) 0.31462(3) 0.0213(2) Uani 1 1 d . . . . .
N1 N -0.0342(7) 0.5709(2) 0.25728(16) 0.0250(9) Uani 1 1 d . . . . .
H1A H -0.105845 0.557468 0.290178 0.030 Uiso 1 1 calc R U . . .
N2 N 0.1632(7) 0.6298(2) 0.25077(15) 0.0226(9) Uani 1 1 d . . . . .
N3 N 0.3923(7) 0.6836(2) 0.16775(15) 0.0213(9) Uani 1 1 d . . . . .
N4 N 0.5635(8) 0.7486(2) 0.25621(15) 0.0222(9) Uani 1 1 d . . . . .
N5 N 0.8528(7) 0.8394(2) 0.31662(14) 0.0211(9) Uani 1 1 d . . . . .
N6 N 0.5505(7) 0.7570(2) 0.37444(15) 0.0209(9) Uani 1 1 d . . . . .
N7 N 0.3686(8) 0.7021(2) 0.46178(15) 0.0231(9) Uani 1 1 d . . . . .
N8 N 0.1376(8) 0.6416(2) 0.37559(15) 0.0248(9) Uani 1 1 d . . . . .
N9 N -0.0758(7) 0.5850(2) 0.36580(16) 0.0245(9) 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 1.342(6) . ?
C1 C2 1.364(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.391(6) . ?
C2 H2 0.9500 . ?
C3 N2 1.355(6) . ?
C3 N3 1.381(6) . ?
C4 N3 1.269(6) . ?
C4 N4 1.421(6) . ?
C4 C5 1.478(6) . ?
C5 C10 1.380(6) . ?
C5 C6 1.392(6) . ?
C6 C7 1.387(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.394(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.467(6) . ?
C11 N5 1.331(5) . ?
C11 N4 1.353(5) . ?
C12 N5 1.330(5) . ?
C12 N6 1.364(5) . ?
C12 C13 1.452(6) . ?
C13 C18 1.388(6) . ?
C13 C14 1.394(6) . ?
C14 C15 1.385(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.393(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.469(6) . ?
C19 N7 1.278(5) . ?
C19 N6 1.422(5) . ?
C20 N8 1.363(6) . ?
C20 N7 1.379(6) . ?
C20 C21 1.393(6) . ?
C21 C22 1.384(6) . ?
C21 H21 0.9500 . ?
C22 N9 1.344(6) . ?
C22 H22 0.9500 . ?
Cu1 N6 1.958(4) . ?
Cu1 N4 1.963(4) . ?
Cu1 N8 1.963(4) . ?
Cu1 N2 1.985(4) . ?
N1 N2 1.360(5) . ?
N1 H1A 0.8800 . ?
N8 N9 1.382(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 108.6(4) . . ?
N1 C1 H1 125.7 . . ?
C2 C1 H1 125.7 . . ?
C1 C2 C3 105.2(4) . . ?
C1 C2 H2 127.4 . . ?
C3 C2 H2 127.4 . . ?
N2 C3 N3 125.0(4) . . ?
N2 C3 C2 110.3(4) . . ?
N3 C3 C2 124.7(4) . . ?
N3 C4 N4 128.8(4) . . ?
N3 C4 C5 123.5(4) . . ?
N4 C4 C5 107.7(4) . . ?
C10 C5 C6 121.3(4) . . ?
C10 C5 C4 107.0(4) . . ?
C6 C5 C4 131.7(4) . . ?
C7 C6 C5 116.9(4) . . ?
C7 C6 H6 121.6 . . ?
C5 C6 H6 121.6 . . ?
C6 C7 C8 121.8(4) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C9 C8 C7 121.0(4) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 117.2(4) . . ?
C8 C9 H9 121.4 . . ?
C10 C9 H9 121.4 . . ?
C5 C10 C9 121.9(4) . . ?
C5 C10 C11 107.1(4) . . ?
C9 C10 C11 131.0(4) . . ?
N5 C11 N4 129.8(4) . . ?
N5 C11 C10 120.0(4) . . ?
N4 C11 C10 110.2(4) . . ?
N5 C12 N6 128.4(4) . . ?
N5 C12 C13 120.7(4) . . ?
N6 C12 C13 110.9(4) . . ?
C18 C13 C14 121.4(4) . . ?
C18 C13 C12 107.4(4) . . ?
C14 C13 C12 131.2(4) . . ?
C15 C14 C13 117.1(4) . . ?
C15 C14 H14 121.4 . . ?
C13 C14 H14 121.4 . . ?
C14 C15 C16 121.5(4) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C17 C16 C15 121.2(4) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C18 C17 C16 117.4(4) . . ?
C18 C17 H17 121.3 . . ?
C16 C17 H17 121.3 . . ?
C13 C18 C17 121.4(4) . . ?
C13 C18 C19 106.2(4) . . ?
C17 C18 C19 132.3(4) . . ?
N7 C19 N6 127.5(4) . . ?
N7 C19 C18 123.5(4) . . ?
N6 C19 C18 109.0(4) . . ?
N8 C20 N7 126.4(4) . . ?
N8 C20 C21 109.7(4) . . ?
N7 C20 C21 123.9(4) . . ?
C22 C21 C20 104.4(4) . . ?
C22 C21 H21 127.8 . . ?
C20 C21 H21 127.8 . . ?
N9 C22 C21 111.0(4) . . ?
N9 C22 H22 124.5 . . ?
C21 C22 H22 124.5 . . ?
N6 Cu1 N4 89.52(15) . . ?
N6 Cu1 N8 87.94(15) . . ?
N4 Cu1 N8 177.37(15) . . ?
N6 Cu1 N2 176.31(14) . . ?
N4 Cu1 N2 87.09(14) . . ?
N8 Cu1 N2 95.47(15) . . ?
C1 N1 N2 110.6(4) . . ?
C1 N1 H1A 124.7 . . ?
N2 N1 H1A 124.7 . . ?
C3 N2 N1 105.3(4) . . ?
C3 N2 Cu1 129.8(3) . . ?
N1 N2 Cu1 124.9(3) . . ?
C4 N3 C3 122.5(4) . . ?
C11 N4 C4 108.0(4) . . ?
C11 N4 Cu1 125.3(3) . . ?
C4 N4 Cu1 126.7(3) . . ?
C12 N5 C11 120.8(4) . . ?
C12 N6 C19 106.5(4) . . ?
C12 N6 Cu1 126.2(3) . . ?
C19 N6 Cu1 127.1(3) . . ?
C19 N7 C20 122.4(4) . . ?
C20 N8 N9 107.5(4) . . ?
C20 N8 Cu1 128.3(3) . . ?
N9 N8 Cu1 124.1(3) . . ?
C22 N9 N8 107.4(4) . . ?

_refine_diff_density_max         0.558
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.112

