# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_f
_database_code_depnum_ccdc_archive 'CCDC 1006963'
loop_
_audit_author_name
_audit_author_address
'Subratanath Koner'
;Jadavpur University
India
;
_audit_update_record             
;
2018-03-16 deposited with the CCDC.	2019-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H9 N3 O8 Zn2'
_chemical_formula_weight         441.95

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   22.8941(17)
_cell_length_b                   11.2210(7)
_cell_length_c                   16.7025(11)
_cell_angle_alpha                90
_cell_angle_beta                 127.370(3)
_cell_angle_gamma                90
_cell_volume                     3410.0(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.722
_exptl_crystal_F_000             1760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    2.855
_shelx_estimated_absorpt_T_min   0.524
_shelx_estimated_absorpt_T_max   0.894
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19091
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.468
_diffrn_reflns_theta_max         28.266
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4204
_reflns_number_gt                3045
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0803P)²+53.8368P] 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         4204
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0632
_refine_ls_wR_factor_ref         0.1962
_refine_ls_wR_factor_gt          0.1849
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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
Zn1 Zn 0.23548(4) 0.28239(6) 0.08962(5) 0.0216(2) Uani 1 1 d . . . . .
Zn2 Zn 0.25588(5) -0.00152(7) 0.20091(6) 0.0306(3) Uani 1 1 d . . . . .
O1 O 0.2143(3) 0.1810(4) 0.1720(3) 0.0263(10) Uani 1 1 d . . . . .
O2 O 0.1966(3) 0.3326(4) 0.2416(4) 0.0277(10) Uani 1 1 d . . . . .
C3 C 0.2095(3) 0.2262(5) 0.2376(5) 0.0198(12) Uani 1 1 d . . . . .
C4 C 0.2207(4) 0.1394(5) 0.3119(5) 0.0222(13) Uani 1 1 d . . . . .
N5 N 0.2397(3) 0.0271(5) 0.3052(4) 0.0238(12) Uani 1 1 d . . . . .
N6 N 0.2450(3) -0.0401(5) 0.3756(4) 0.0237(11) Uani 1 1 d . . . . .
C7 C 0.2294(4) 0.0307(5) 0.4269(5) 0.0246(14) Uani 1 1 d . . . . .
C8 C 0.2144(4) 0.1470(5) 0.3897(5) 0.0250(14) Uani 1 1 d . . . . .
H8 H 0.2028 0.2145 0.4119 0.030 Uiso 1 1 calc R U . . .
C9 C 0.2315(4) -0.0260(5) 0.5076(5) 0.0234(13) Uani 1 1 d . . . . .
O10 O 0.2233(3) 0.0372(4) 0.5624(4) 0.0335(12) Uani 1 1 d . . . . .
O11 O 0.2415(3) -0.1402(4) 0.5160(3) 0.0245(10) Uani 1 1 d . . . . .
O12 O 0.3491(3) 0.2539(4) 0.2139(4) 0.0342(11) Uani 1 1 d . . . . .
O13 O 0.3575(3) 0.0619(4) 0.2575(4) 0.0389(12) Uani 1 1 d . . . . .
C14 C 0.3839(4) 0.1634(6) 0.2636(5) 0.0286(14) Uani 1 1 d . . . . .
C15 C 0.4657(4) 0.1747(6) 0.3378(5) 0.0270(14) Uani 1 1 d . . . . .
C16 C 0.5089(5) 0.0815(8) 0.3961(9) 0.066(3) Uani 1 1 d . . . . .
H16 H 0.4872 0.0067 0.3906 0.079 Uiso 1 1 calc R U . . .
C17 C 0.5851(5) 0.0958(8) 0.4641(9) 0.068(3) Uani 1 1 d . . . . .
H17 H 0.6142 0.0292 0.5035 0.081 Uiso 1 1 calc R U . . .
N18 N 0.6187(3) 0.1971(5) 0.4760(4) 0.0269(12) Uani 1 1 d . . . . .
C19 C 0.5762(5) 0.2873(8) 0.4200(8) 0.063(3) Uani 1 1 d . . . . .
H19 H 0.5989 0.3618 0.4278 0.075 Uiso 1 1 calc R U . . .
C20 C 0.5006(5) 0.2796(8) 0.3503(8) 0.060(3) Uani 1 1 d . . . . .
H20 H 0.4729 0.3474 0.3113 0.072 Uiso 1 1 calc R U . . .
O21 O 0.1397(6) -0.0950(11) 0.1261(8) 0.122(4) Uani 1 1 d . . . . .
O100 O 0.4176(15) -0.140(3) 0.186(2) 0.171(12) Uani 0.5 1 d . . P . .
O200 O 0.0992(13) -0.271(2) -0.016(2) 0.144(10) Uani 0.5 1 d . . P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N6 2.047(5) 4 ?
Zn1 O1 2.057(4) . ?
Zn1 O11 2.070(4) 6 ?
Zn1 O12 2.150(5) . ?
Zn1 N18 2.154(6) 8_455 ?
Zn1 O11 2.295(4) 4 ?
Zn2 O10 1.994(5) 6 ?
Zn2 N5 2.015(5) . ?
Zn2 O13 2.035(5) . ?
Zn2 O2 2.075(4) 4_545 ?
Zn2 O1 2.185(4) . ?
Zn2 O21 2.387(10) . ?
O1 C3 1.271(7) . ?
O2 C3 1.241(7) . ?
O2 Zn2 2.075(4) 4 ?
C3 C4 1.472(8) . ?
C4 N5 1.359(8) . ?
C4 C8 1.394(8) . ?
N5 N6 1.338(7) . ?
N6 C7 1.366(7) . ?
N6 Zn1 2.047(5) 4_545 ?
C7 C8 1.395(8) . ?
C7 C9 1.466(8) . ?
C8 H8 0.9500 . ?
C9 O10 1.258(7) . ?
C9 O11 1.295(7) . ?
O10 Zn2 1.994(5) 6_556 ?
O11 Zn1 2.070(4) 6_556 ?
O11 Zn1 2.295(4) 4_545 ?
O12 C14 1.246(8) . ?
O13 C14 1.264(8) . ?
C14 C15 1.497(10) . ?
C15 C16 1.361(11) . ?
C15 C20 1.366(10) . ?
C16 C17 1.399(13) . ?
C16 H16 0.9500 . ?
C17 N18 1.318(10) . ?
C17 H17 0.9500 . ?
N18 C19 1.320(10) . ?
N18 Zn1 2.154(6) 8_556 ?
C19 C20 1.384(13) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?

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
N6 Zn1 O1 116.57(18) 4 . ?
N6 Zn1 O11 146.84(18) 4 6 ?
O1 Zn1 O11 95.70(17) . 6 ?
N6 Zn1 O12 86.7(2) 4 . ?
O1 Zn1 O12 84.83(19) . . ?
O11 Zn1 O12 88.93(19) 6 . ?
N6 Zn1 N18 94.9(2) 4 8_455 ?
O1 Zn1 N18 88.8(2) . 8_455 ?
O11 Zn1 N18 93.1(2) 6 8_455 ?
O12 Zn1 N18 173.4(2) . 8_455 ?
N6 Zn1 O11 74.80(17) 4 4 ?
O1 Zn1 O11 168.58(16) . 4 ?
O11 Zn1 O11 72.89(18) 6 4 ?
O12 Zn1 O11 95.21(18) . 4 ?
N18 Zn1 O11 91.35(19) 8_455 4 ?
O10 Zn2 N5 154.1(2) 6 . ?
O10 Zn2 O13 97.2(2) 6 . ?
N5 Zn2 O13 107.5(2) . . ?
O10 Zn2 O2 94.48(19) 6 4_545 ?
N5 Zn2 O2 93.63(19) . 4_545 ?
O13 Zn2 O2 88.2(2) . 4_545 ?
O10 Zn2 O1 97.26(19) 6 . ?
N5 Zn2 O1 75.96(18) . . ?
O13 Zn2 O1 89.79(19) . . ?
O2 Zn2 O1 168.25(17) 4_545 . ?
O10 Zn2 O21 77.9(3) 6 . ?
N5 Zn2 O21 78.0(3) . . ?
O13 Zn2 O21 173.1(4) . . ?
O2 Zn2 O21 87.3(3) 4_545 . ?
O1 Zn2 O21 95.7(3) . . ?
C3 O1 Zn1 122.3(4) . . ?
C3 O1 Zn2 116.0(4) . . ?
Zn1 O1 Zn2 114.71(19) . . ?
C3 O2 Zn2 144.3(5) . 4 ?
O2 C3 O1 125.4(6) . . ?
O2 C3 C4 121.0(5) . . ?
O1 C3 C4 113.6(5) . . ?
N5 C4 C8 110.6(5) . . ?
N5 C4 C3 116.5(5) . . ?
C8 C4 C3 133.0(5) . . ?
N6 N5 C4 108.3(5) . . ?
N6 N5 Zn2 134.7(4) . . ?
C4 N5 Zn2 117.0(4) . . ?
N5 N6 C7 107.7(5) . . ?
N5 N6 Zn1 133.3(4) . 4_545 ?
C7 N6 Zn1 118.9(4) . 4_545 ?
N6 C7 C8 110.6(5) . . ?
N6 C7 C9 116.7(5) . . ?
C8 C7 C9 132.7(5) . . ?
C4 C8 C7 102.8(5) . . ?
C4 C8 H8 128.6 . . ?
C7 C8 H8 128.6 . . ?
O10 C9 O11 125.1(6) . . ?
O10 C9 C7 119.2(5) . . ?
O11 C9 C7 115.7(5) . . ?
C9 O10 Zn2 127.9(4) . 6_556 ?
C9 O11 Zn1 139.1(4) . 6_556 ?
C9 O11 Zn1 113.6(4) . 4_545 ?
Zn1 O11 Zn1 107.12(18) 6_556 4_545 ?
C14 O12 Zn1 132.3(5) . . ?
C14 O13 Zn2 135.1(5) . . ?
O12 C14 O13 126.9(7) . . ?
O12 C14 C15 117.1(6) . . ?
O13 C14 C15 116.1(6) . . ?
C16 C15 C20 116.7(7) . . ?
C16 C15 C14 121.9(7) . . ?
C20 C15 C14 121.4(7) . . ?
C15 C16 C17 119.9(8) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
N18 C17 C16 123.3(8) . . ?
N18 C17 H17 118.4 . . ?
C16 C17 H17 118.4 . . ?
C17 N18 C19 116.3(7) . . ?
C17 N18 Zn1 121.6(5) . 8_556 ?
C19 N18 Zn1 122.0(5) . 8_556 ?
N18 C19 C20 123.8(8) . . ?
N18 C19 H19 118.1 . . ?
C20 C19 H19 118.1 . . ?
C15 C20 C19 120.0(8) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?

_refine_diff_density_max         1.473
_refine_diff_density_min         -0.861
_refine_diff_density_rms         0.176

_shelxl_version_number           2013-4


_chemical_properties_physical    Air-sensitive
