# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2238980'
loop_
_audit_author_name
_audit_author_address
'Sangita Sahoo'
;IIT Madras
India
;
_audit_update_record             
;
2023-01-31 deposited with the CCDC.	2023-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H18 N4 O4 Zn'
_chemical_formula_weight         347.67

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'
Zn Zn -1.5491 0.6778 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   9.374(2)
_cell_length_b                   8.2061(18)
_cell_length_c                   10.172(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.621(10)
_cell_angle_gamma                90
_cell_volume                     782.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6773
_cell_measurement_theta_min      4.35
_cell_measurement_theta_max      68.24

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    2.374
_shelx_estimated_absorpt_T_min   0.653
_shelx_estimated_absorpt_T_max   0.780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.579768
_exptl_absorpt_correction_T_max  0.753056
_exptl_absorpt_process_details   'TWINABS - Bruker AXS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture Diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1514
_diffrn_reflns_av_unetI/netI     0.0380
_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       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.347
_diffrn_reflns_theta_max         68.232
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.528
_diffrn_reflns_point_group_measured_fraction_full 0.530
_reflns_number_total             1514
_reflns_number_gt                1487
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX3(Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  ?
_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)+(0.0559P)²+0.3989P] 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   0.07(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1514
_refine_ls_number_parameters     195
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.1005
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   1.238
_refine_ls_restrained_S_all      1.237
_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 0.5463(6) 0.2333(9) 0.9187(5) 0.0386(13) Uani 1 1 d . . . . .
H1 H 0.604583 0.238755 0.995518 0.046 Uiso 1 1 calc R U . . .
C2 C 0.4142(6) 0.1664(8) 0.9118(5) 0.0386(13) Uani 1 1 d . . . . .
H2 H 0.362424 0.119726 0.982156 0.046 Uiso 1 1 calc R U . . .
C3 C 0.4730(5) 0.2573(6) 0.7185(5) 0.0261(10) Uani 1 1 d . . . . .
H3 H 0.468373 0.284466 0.627754 0.031 Uiso 1 1 calc R U . . .
C4 C 0.2349(6) 0.1215(10) 0.7251(6) 0.0373(14) Uani 1 1 d . . . . .
H4A H 0.157631 0.195474 0.749814 0.056 Uiso 1 1 calc R U . . .
H4B H 0.214360 0.011768 0.757809 0.056 Uiso 1 1 calc R U . . .
H4C H 0.242688 0.118683 0.629130 0.056 Uiso 1 1 calc R U . . .
C5 C 0.9559(5) 0.3269(7) 0.5137(5) 0.0325(11) Uani 1 1 d . . . . .
H5 H 1.035961 0.375408 0.556282 0.039 Uiso 1 1 calc R U . . .
C6 C 0.9573(5) 0.2565(7) 0.3936(5) 0.0307(11) Uani 1 1 d . . . . .
H6 H 1.036525 0.246567 0.336693 0.037 Uiso 1 1 calc R U . . .
C7 C 0.7419(5) 0.2413(7) 0.4744(4) 0.0281(10) Uani 1 1 d . . . . .
H7 H 0.643081 0.218077 0.482635 0.034 Uiso 1 1 calc R U . . .
C8 C 0.7683(7) 0.1219(11) 0.2511(4) 0.0386(16) Uani 1 1 d . . . . .
H8A H 0.666228 0.098841 0.259344 0.058 Uiso 1 1 calc R U . . .
H8B H 0.820280 0.019571 0.238342 0.058 Uiso 1 1 calc R U . . .
H8C H 0.783533 0.193565 0.175506 0.058 Uiso 1 1 calc R U . . .
C9 C 0.6457(5) 0.7000(6) 0.6658(5) 0.0264(10) Uani 1 1 d . . . . .
C10 C 0.6270(8) 0.8822(10) 0.6733(8) 0.0600(18) Uani 1 1 d . . . . .
H10A H 0.608155 0.913937 0.764326 0.090 Uiso 1 1 calc R U . . .
H10B H 0.546616 0.915239 0.616963 0.090 Uiso 1 1 calc R U . . .
H10C H 0.714225 0.936015 0.643401 0.090 Uiso 1 1 calc R U . . .
C11 C 0.9412(5) 0.3918(9) 0.9548(5) 0.0299(10) Uani 1 1 d . . . . .
C12 C 1.0785(6) 0.3900(13) 1.0345(5) 0.0506(16) Uani 1 1 d . . . . .
H12A H 1.067234 0.457436 1.113226 0.076 Uiso 1 1 calc R U . . .
H12B H 1.156272 0.433437 0.981282 0.076 Uiso 1 1 calc R U . . .
H12C H 1.100908 0.277839 1.060678 0.076 Uiso 1 1 calc R U . . .
N1 N 0.5825(4) 0.2918(5) 0.7974(4) 0.0272(9) Uani 1 1 d . . . . .
N2 N 0.3701(4) 0.1795(6) 0.7830(4) 0.0287(9) Uani 1 1 d . . . . .
N3 N 0.8208(4) 0.3176(5) 0.5648(4) 0.0266(9) Uani 1 1 d . . . . .
N4 N 0.8204(4) 0.2020(5) 0.3708(4) 0.0267(9) Uani 1 1 d . . . . .
Zn1 Zn 0.76324(5) 0.40345(8) 0.74395(5) 0.0233(2) Uani 1 1 d . . . . .
O1 O 0.7379(3) 0.6421(5) 0.7455(3) 0.0298(8) Uani 1 1 d . . . . .
O2 O 0.5732(4) 0.6175(5) 0.5877(3) 0.0363(9) Uani 1 1 d . . . . .
O3 O 0.9531(4) 0.3768(5) 0.8299(3) 0.0339(9) Uani 1 1 d . . . . .
O4 O 0.8260(3) 0.4014(8) 1.0101(3) 0.0420(8) 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 1.355(7) . ?
C1 N1 1.370(6) . ?
C1 H1 0.9500 . ?
C2 N2 1.374(6) . ?
C2 H2 0.9500 . ?
C3 N1 1.327(6) . ?
C3 N2 1.335(6) . ?
C3 H3 0.9500 . ?
C4 N2 1.471(7) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.351(7) . ?
C5 N3 1.377(6) . ?
C5 H5 0.9500 . ?
C6 N4 1.376(6) . ?
C6 H6 0.9500 . ?
C7 N3 1.330(6) . ?
C7 N4 1.332(6) . ?
C7 H7 0.9500 . ?
C8 N4 1.463(6) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 O2 1.240(6) . ?
C9 O1 1.271(6) . ?
C9 C10 1.508(9) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O4 1.226(6) . ?
C11 O3 1.282(6) . ?
C11 C12 1.514(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N1 Zn1 2.006(4) . ?
N3 Zn1 2.032(4) . ?
Zn1 O1 1.973(4) . ?
Zn1 O3 1.986(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
C2 C1 N1 109.3(4) . . ?
C2 C1 H1 125.3 . . ?
N1 C1 H1 125.3 . . ?
C1 C2 N2 106.4(5) . . ?
C1 C2 H2 126.8 . . ?
N2 C2 H2 126.8 . . ?
N1 C3 N2 111.3(4) . . ?
N1 C3 H3 124.3 . . ?
N2 C3 H3 124.3 . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N3 109.6(5) . . ?
C6 C5 H5 125.2 . . ?
N3 C5 H5 125.2 . . ?
C5 C6 N4 105.8(4) . . ?
C5 C6 H6 127.1 . . ?
N4 C6 H6 127.1 . . ?
N3 C7 N4 110.6(4) . . ?
N3 C7 H7 124.7 . . ?
N4 C7 H7 124.7 . . ?
N4 C8 H8A 109.5 . . ?
N4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 O1 124.6(5) . . ?
O2 C9 C10 120.7(5) . . ?
O1 C9 C10 114.6(5) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O4 C11 O3 123.2(4) . . ?
O4 C11 C12 120.2(4) . . ?
O3 C11 C12 116.6(4) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C3 N1 C1 105.8(4) . . ?
C3 N1 Zn1 125.7(3) . . ?
C1 N1 Zn1 128.5(3) . . ?
C3 N2 C2 107.1(4) . . ?
C3 N2 C4 125.6(4) . . ?
C2 N2 C4 127.3(5) . . ?
C7 N3 C5 105.8(4) . . ?
C7 N3 Zn1 129.2(3) . . ?
C5 N3 Zn1 125.0(3) . . ?
C7 N4 C6 108.1(4) . . ?
C7 N4 C8 125.8(4) . . ?
C6 N4 C8 126.1(4) . . ?
O1 Zn1 O3 102.31(16) . . ?
O1 Zn1 N1 110.41(16) . . ?
O3 Zn1 N1 125.87(17) . . ?
O1 Zn1 N3 112.61(16) . . ?
O3 Zn1 N3 96.39(15) . . ?
N1 Zn1 N3 108.53(16) . . ?
C9 O1 Zn1 116.6(3) . . ?
C11 O3 Zn1 109.8(3) . . ?

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
N1 C1 C2 N2 1.9(8) . . . . ?
N3 C5 C6 N4 -0.3(6) . . . . ?
N2 C3 N1 C1 -0.3(6) . . . . ?
N2 C3 N1 Zn1 178.6(3) . . . . ?
C2 C1 N1 C3 -1.0(7) . . . . ?
C2 C1 N1 Zn1 -179.9(4) . . . . ?
N1 C3 N2 C2 1.5(6) . . . . ?
N1 C3 N2 C4 -179.2(5) . . . . ?
C1 C2 N2 C3 -2.0(7) . . . . ?
C1 C2 N2 C4 178.7(6) . . . . ?
N4 C7 N3 C5 0.4(6) . . . . ?
N4 C7 N3 Zn1 -178.8(3) . . . . ?
C6 C5 N3 C7 0.0(6) . . . . ?
C6 C5 N3 Zn1 179.2(4) . . . . ?
N3 C7 N4 C6 -0.6(6) . . . . ?
N3 C7 N4 C8 -177.9(5) . . . . ?
C5 C6 N4 C7 0.6(6) . . . . ?
C5 C6 N4 C8 177.9(6) . . . . ?
O2 C9 O1 Zn1 -0.8(6) . . . . ?
C10 C9 O1 Zn1 178.3(4) . . . . ?
O4 C11 O3 Zn1 8.0(8) . . . . ?
C12 C11 O3 Zn1 -174.7(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 O4 0.95 2.47 3.097(7) 123.4 . yes
C2 H2 O4 0.95 2.52 3.236(7) 132.5 2_647 yes
C3 H3 O2 0.95 2.61 3.343(6) 134.2 2_646 yes
C4 H4A O3 0.98 2.57 3.545(8) 175.8 1_455 yes
C4 H4B O4 0.98 2.56 3.298(8) 132.0 2_647 yes
C6 H6 O1 0.95 2.44 3.337(6) 157.7 2_746 yes
C7 H7 O2 0.95 2.30 3.181(6) 154.6 2_646 yes
C8 H8B O3 0.98 2.53 3.404(8) 148.6 2_746 yes
C8 H8C O4 0.98 2.43 3.405(9) 172.1 1_554 yes

_refine_diff_density_max         0.451
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.120

