# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_ov_zn-bbta-kira_auto
_database_code_depnum_ccdc_archive 'CCDC 2145009'
loop_
_audit_author_name
_audit_author_address
'Mohammad Rasel Mian'
;Northwestern University
United States of America
;
_audit_update_record             
;
2022-01-27 deposited with the CCDC.	2022-02-25 downloaded from the CCDC.
;
_audit_creation_date             2022-01-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        NU-251
_chemical_formula_moiety         'C10 H10 N4 O4 Zn'
_chemical_formula_sum            'C10 H10 N4 O4 Zn'
_chemical_formula_weight         315.59
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   24.4357(10)
_cell_length_b                   9.0502(4)
_cell_length_c                   13.1766(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.775(4)
_cell_angle_gamma                90
_cell_volume                     2903.9(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    300
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      79.9
_cell_measurement_theta_min      3.6
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.864
_exptl_absorpt_coefficient_mu    2.508
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9848
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.922
_diffrn_reflns_theta_min         3.630
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2348
_reflns_number_total             3000
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.778
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3000
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0477
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0668P)²+4.8548P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1289
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3A), C7(H7), C8(H8)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.67978(2) 0.08155(5) 0.77401(3) 0.02377(16) Uani 1 1 d . . . . .
O4 O 0.66585(10) 0.1856(3) 0.90029(17) 0.0292(5) Uani 1 1 d . . . . .
O1 O 0.62243(10) 0.0044(3) 0.67710(18) 0.0339(6) Uani 1 1 d . . . . .
N3 N 0.77736(12) 0.4055(3) 0.67276(19) 0.0228(6) Uani 1 1 d . . . . .
N1 N 0.72552(12) 0.2155(3) 0.69557(19) 0.0233(6) Uani 1 1 d . . . . .
O2 O 0.58373(13) 0.2255(4) 0.6863(2) 0.0453(7) Uani 1 1 d . . . . .
N2 N 0.75145(12) 0.3306(3) 0.7400(2) 0.0245(6) Uani 1 1 d . . . . .
O3 O 0.49092(15) 0.2778(4) 0.5848(3) 0.0560(9) Uani 1 1 d . . . . .
H3 H 0.518176 0.295980 0.625973 0.084 Uiso 1 1 calc R U . . .
N4 N 0.64401(14) 0.3866(4) 0.9875(3) 0.0376(8) Uani 1 1 d . . . . .
C2 C 0.76776(13) 0.3404(4) 0.5786(2) 0.0212(7) Uani 1 1 d . . . . .
C1 C 0.73393(14) 0.2162(4) 0.5933(2) 0.0218(7) Uani 1 1 d . . . . .
C3 C 0.78500(14) 0.3791(4) 0.4846(2) 0.0236(7) Uani 1 1 d . . . . .
H3A H 0.807514 0.462540 0.474475 0.028 Uiso 1 1 calc R U . . .
C4 C 0.58537(16) 0.0980(5) 0.6503(3) 0.0340(8) Uani 1 1 d . . . . .
C5 C 0.54122(16) 0.0486(5) 0.5719(3) 0.0346(9) Uani 1 1 d . . . . .
C7 C 0.45539(17) 0.0908(5) 0.4735(3) 0.0402(9) Uani 1 1 d . . . . .
H7 H 0.424530 0.151951 0.455415 0.048 Uiso 1 1 calc R U . . .
C8 C 0.64192(16) 0.3069(4) 0.9045(3) 0.0330(8) Uani 1 1 d . . . . .
H8 H 0.621406 0.342685 0.845145 0.040 Uiso 1 1 calc R U . . .
C6 C 0.49635(18) 0.1410(5) 0.5446(3) 0.0406(10) Uani 1 1 d . . . . .
C9 C 0.67635(18) 0.3363(5) 1.0797(3) 0.0401(10) Uani 1 1 d . . . . .
H9A H 0.657092 0.254967 1.110595 0.060 Uiso 1 1 calc R U . . .
H9B H 0.681231 0.418181 1.128242 0.060 Uiso 1 1 calc R U . . .
H9C H 0.712365 0.301921 1.061886 0.060 Uiso 1 1 calc R U . . .
C10 C 0.6139(3) 0.5243(7) 0.9920(5) 0.085(2) Uani 1 1 d . . . . .
H10A H 0.638823 0.602714 1.018275 0.128 Uiso 1 1 calc R U . . .
H10B H 0.584275 0.512441 1.037134 0.128 Uiso 1 1 calc R U . . .
H10C H 0.598172 0.550678 0.923514 0.128 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
Zn1 O4 1.966(2) . ?
Zn1 O1 1.945(2) . ?
Zn1 N3 2.001(3) 4_646 ?
Zn1 N1 1.995(3) . ?
O4 C8 1.247(4) . ?
O1 C4 1.268(5) . ?
N3 N2 1.319(4) . ?
N3 C2 1.376(4) . ?
N1 N2 1.330(4) . ?
N1 C1 1.380(4) . ?
O2 C4 1.249(5) . ?
O3 H3 0.8400 . ?
O3 C6 1.357(5) . ?
N4 C8 1.308(5) . ?
N4 C9 1.466(5) . ?
N4 C10 1.451(6) . ?
C2 C1 1.418(5) . ?
C2 C3 1.386(4) . ?
C1 C3 1.390(4) 7_656 ?
C3 H3A 0.9500 . ?
C4 C5 1.499(5) . ?
C5 C7 1.401(6) 5_656 ?
C5 C6 1.402(6) . ?
C7 H7 0.9500 . ?
C7 C6 1.389(6) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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
O4 Zn1 N3 101.95(10) . 4_646 ?
O4 Zn1 N1 106.95(11) . . ?
O1 Zn1 O4 124.16(11) . . ?
O1 Zn1 N3 105.77(11) . 4_646 ?
O1 Zn1 N1 106.38(11) . . ?
N1 Zn1 N3 111.46(12) . 4_646 ?
C8 O4 Zn1 125.0(2) . . ?
C4 O1 Zn1 113.7(3) . . ?
N2 N3 Zn1 116.1(2) . 4_656 ?
N2 N3 C2 109.3(3) . . ?
C2 N3 Zn1 134.6(2) . 4_656 ?
N2 N1 Zn1 121.0(2) . . ?
N2 N1 C1 108.8(3) . . ?
C1 N1 Zn1 130.1(2) . . ?
N3 N2 N1 110.1(2) . . ?
C6 O3 H3 109.5 . . ?
C8 N4 C9 120.1(3) . . ?
C8 N4 C10 121.5(4) . . ?
C10 N4 C9 118.3(4) . . ?
N3 C2 C1 105.9(3) . . ?
N3 C2 C3 131.0(3) . . ?
C3 C2 C1 123.1(3) . . ?
N1 C1 C2 105.8(3) . . ?
N1 C1 C3 130.6(3) . 7_656 ?
C3 C1 C2 123.6(3) 7_656 . ?
C2 C3 C1 113.3(3) . 7_656 ?
C2 C3 H3A 123.3 . . ?
C1 C3 H3A 123.3 7_656 . ?
O1 C4 C5 116.7(4) . . ?
O2 C4 O1 123.7(3) . . ?
O2 C4 C5 119.6(4) . . ?
C7 C5 C4 119.9(4) 5_656 . ?
C7 C5 C6 120.0(4) 5_656 . ?
C6 C5 C4 120.1(4) . . ?
C5 C7 H7 119.4 5_656 . ?
C6 C7 C5 121.2(4) . 5_656 ?
C6 C7 H7 119.4 . . ?
O4 C8 N4 122.5(3) . . ?
O4 C8 H8 118.8 . . ?
N4 C8 H8 118.8 . . ?
O3 C6 C5 122.9(4) . . ?
O3 C6 C7 118.2(4) . . ?
C7 C6 C5 118.8(4) . . ?
N4 C9 H9A 109.5 . . ?
N4 C9 H9B 109.5 . . ?
N4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
N4 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O4 C8 N4 -164.7(3) . . . . ?
Zn1 O1 C4 O2 -3.7(5) . . . . ?
Zn1 O1 C4 C5 177.1(3) . . . . ?
Zn1 N3 N2 N1 -178.9(2) 4_656 . . . ?
Zn1 N3 C2 C1 179.4(2) 4_656 . . . ?
Zn1 N3 C2 C3 -1.1(6) 4_656 . . . ?
Zn1 N1 N2 N3 -177.8(2) . . . . ?
Zn1 N1 C1 C2 176.9(2) . . . . ?
Zn1 N1 C1 C3 -3.0(5) . . . 7_656 ?
O1 C4 C5 C7 -4.8(6) . . . 5_656 ?
O1 C4 C5 C6 174.6(4) . . . . ?
N3 C2 C1 N1 0.0(4) . . . . ?
N3 C2 C1 C3 179.9(3) . . . 7_656 ?
N3 C2 C3 C1 -179.8(3) . . . 7_656 ?
O2 C4 C5 C7 176.0(4) . . . 5_656 ?
O2 C4 C5 C6 -4.6(6) . . . . ?
N2 N3 C2 C1 -0.8(4) . . . . ?
N2 N3 C2 C3 178.7(3) . . . . ?
N2 N1 C1 C2 0.7(4) . . . . ?
N2 N1 C1 C3 -179.2(3) . . . 7_656 ?
C2 N3 N2 N1 1.2(4) . . . . ?
C1 N1 N2 N3 -1.2(4) . . . . ?
C1 C2 C3 C1 -0.3(5) . . . 7_656 ?
C3 C2 C1 N1 -179.5(3) . . . . ?
C3 C2 C1 C3 0.4(6) . . . 7_656 ?
C4 C5 C6 O3 1.4(7) . . . . ?
C4 C5 C6 C7 -178.4(4) . . . . ?
C5 C7 C6 O3 179.2(4) 5_656 . . . ?
C5 C7 C6 C5 -1.0(7) 5_656 . . . ?
C7 C5 C6 O3 -179.2(4) 5_656 . . . ?
C7 C5 C6 C7 1.0(7) 5_656 . . . ?
C9 N4 C8 O4 1.4(6) . . . . ?
C10 N4 C8 O4 -177.2(5) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 -0.193 0.250 161.5 36.9 '2 DMF'
2 0.000 0.193 0.750 161.5 36.9 '2 DMF'
3 0.500 0.307 0.250 161.5 36.9 '2 DMF'
4 0.500 0.693 0.750 161.5 36.9 '2 DMF'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
