# 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 2019

####################################################################### 
# 
# 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_1183ex_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1912778'
loop_
_audit_author_name
_audit_author_address
'Mohammad Mir'
;Aliah University
India
;
_audit_update_record             
;
2019-04-29 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;
_audit_creation_date             2019-03-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'0.06(C26.15 H28 N2 O8 Zn2), 0.06(C24.96 H22 N2 O8 Zn2), 0.18(O), 0.06(C)'
_chemical_formula_sum            'C H Cd N O Zn'
_chemical_formula_weight         220.80
_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 0.0033 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'
Cd Cd -0.8075 1.2024 '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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3924(12)
_cell_length_b                   11.0752(16)
_cell_length_c                   16.470(2)
_cell_angle_alpha                97.593(5)
_cell_angle_beta                 92.113(5)
_cell_angle_gamma                112.088(5)
_cell_volume                     1399.8(4)
_cell_formula_units_Z            17
_cell_measurement_reflns_used    9935
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      28.53
_cell_measurement_theta_min      2.81
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    13.485
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5800
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1367 before and 0.0840 after correction.
The Ratio of minimum to maximum transmission is 0.7778.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    4.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             1700
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_Laue_measured_fraction_full 0.941
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18278
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.535
_diffrn_reflns_theta_min         2.531
_diffrn_ambient_temperature      291.06
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4444
_reflns_number_total             6727
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         6.238
_refine_diff_density_min         -6.346
_refine_diff_density_rms         0.376
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.466
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         6727
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1955
_refine_ls_R_factor_gt           0.1615
_refine_ls_restrained_S_all      2.466
_refine_ls_shift/su_max          0.502
_refine_ls_shift/su_mean         0.043
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.5102
_refine_ls_wR_factor_ref         0.5690
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(C22A)=Sof(C21A)=1-FVAR(1)
 Sof(C20)=Sof(C21)=Sof(C22)=FVAR(1)
 Sof(C23A)=1-FVAR(2)
 Sof(C23)=Sof(C24)=FVAR(2)
 Fixed Sof: O10(0.5) C20A(0.5)
3.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5), C13(H13), C10(H10)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B), C6(H6A,H6B), C14(H14A,H14B), C15(H15A,
 H15B), C11(H11A,H11B), C12(H12A,H12B)
3.c Aromatic/amide H refined with riding coordinates:
 C23(H23), C24(H24), C26(H26), C27(H27), C22(H22)
3.d Fitted hexagon refined as free rotating group:
 N1(C18,C19,C20,C21,C22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
N2 N 0.653(3) 0.355(3) 0.5053(18) 0.156(9) Uiso 1 1 d . . . . .
C23 C 0.763(3) 0.388(2) 0.4362(15) 0.112(8) Uiso 1.038(13) 1 d . . P A 1
H23 H 0.776323 0.329367 0.393917 0.134 Uiso 1 1 calc R U . A 1
C24 C 0.864(4) 0.566(3) 0.450(2) 0.179(14) Uiso 1.038(13) 1 d . . P A 1
H24 H 0.952504 0.616916 0.422252 0.215 Uiso 1 1 calc R U . A 1
C25 C 0.7977(8) 0.6044(6) 0.5007(4) -0.0005(11) Uiso 1 1 d . . . A 1
C26 C 0.702(3) 0.555(2) 0.5601(14) 0.104(7) Uiso 1 1 d . . . . .
H26 H 0.673104 0.608301 0.600614 0.125 Uiso 1 1 calc R U . A 1
C27 C 0.647(2) 0.4199(17) 0.5585(11) 0.071(5) Uiso 1 1 d . . . . .
H27 H 0.602628 0.384512 0.604854 0.085 Uiso 1 1 calc R U . . .
N1 N 0.6731(10) 0.8435(7) -0.0008(4) 0.0218(17) Uani 1 1 d G . . . .
C18 C 0.6390(16) 0.9253(11) 0.0616(6) 0.071(5) Uiso 1 1 d G . . B .
C19 C 0.712(2) 1.0614(10) 0.0649(10) 0.094(7) Uiso 1 1 d G . . B .
C20 C 0.819(3) 1.1157(8) 0.0056(14) 0.104(19) Uiso 0.49(3) 1 d G . P B 1
C21 C 0.853(3) 1.0338(14) -0.0568(13) 0.088(14) Uiso 0.49(3) 1 d G . P B 1
C22 C 0.780(2) 0.8977(13) -0.0601(8) 0.047(7) Uiso 0.49(3) 1 d G . P B 1
H22 H 0.802796 0.842950 -0.101853 0.056 Uiso 1 1 calc R U . B 1
Zn2 Zn 0.57101(10) 0.64172(8) -0.00037(5) 0.0120(5) Uani 1 1 d . . . . .
Zn1 Zn 0.57115(15) 0.14116(12) 0.49887(8) 0.0345(5) Uani 1 1 d . . . . .
O3 O 1.4378(11) 0.6344(9) 0.1004(5) 0.042(2) Uani 1 1 d . . . . .
O4 O 1.3306(12) 0.4196(9) 0.1015(5) 0.042(2) Uani 1 1 d . . . . .
O1 O 0.7669(12) 0.6270(11) 0.0709(6) 0.052(3) Uani 1 1 d . . . . .
O2 O 0.6557(11) 0.4090(11) 0.0738(6) 0.050(3) Uani 1 1 d . . . . .
C3 C 1.0771(12) 0.6629(9) 0.1525(6) 0.0225(19) Uani 1 1 d . . . . .
H3A H 1.048853 0.740638 0.161080 0.027 Uiso 1 1 calc R U . . .
H3B H 1.115514 0.655658 0.097929 0.027 Uiso 1 1 calc R U . . .
C4 C 1.2236(12) 0.6793(11) 0.2165(6) 0.026(2) Uani 1 1 d . . . . .
H4A H 1.190771 0.697433 0.271226 0.031 Uiso 1 1 calc R U . . .
H4B H 1.326176 0.753863 0.208729 0.031 Uiso 1 1 calc R U . . .
C7 C 0.9570(12) 0.4166(10) 0.1519(7) 0.025(2) Uani 1 1 d . . . . .
H7A H 0.854641 0.342476 0.160478 0.030 Uiso 1 1 calc R U . . .
H7B H 0.989252 0.396858 0.097283 0.030 Uiso 1 1 calc R U . . .
C1 C 0.7658(10) 0.5232(10) 0.0948(5) 0.0219(19) Uani 1 1 d . . . . .
C8 C 1.3512(10) 0.5349(10) 0.1300(5) 0.0189(17) Uani 1 1 d . . . . .
C2 C 0.9159(10) 0.5412(9) 0.1577(5) 0.0170(17) Uani 1 1 d . . . . .
H2 H 0.877305 0.554576 0.212351 0.020 Uiso 1 1 calc R U . . .
C5 C 1.2646(11) 0.5546(10) 0.2093(5) 0.0227(19) Uani 1 1 d . . . . .
H5 H 1.347326 0.566294 0.256109 0.027 Uiso 1 1 calc R U . . .
C6 C 1.1039(13) 0.4343(12) 0.2158(6) 0.031(2) Uani 1 1 d . . . . .
H6A H 1.066229 0.443348 0.270427 0.037 Uiso 1 1 calc R U . . .
H6B H 1.131615 0.356306 0.208144 0.037 Uiso 1 1 calc R U . . .
O7 O 1.2330(15) -0.1257(12) 0.4305(7) 0.065(3) Uani 1 1 d . . . . .
O6 O 0.5597(14) -0.1314(11) 0.3981(6) 0.056(3) Uani 1 1 d . . . . .
O5 O 0.6658(14) 0.0782(11) 0.3970(6) 0.056(3) Uani 1 1 d . . . . .
C14 C 0.9209(15) -0.1647(12) 0.3472(9) 0.042(3) Uani 1 1 d . . . . .
H14A H 0.948574 -0.242642 0.338018 0.051 Uiso 1 1 calc R U . . .
H14B H 0.882939 -0.158111 0.401989 0.051 Uiso 1 1 calc R U . . .
O8 O 1.3436(13) 0.0903(12) 0.4272(7) 0.065(3) Uani 1 1 d . . . . .
C15 C 0.7738(15) -0.1801(12) 0.2839(8) 0.039(3) Uani 1 1 d . . . . .
H15A H 0.805569 -0.199188 0.229069 0.047 Uiso 1 1 calc R U . . .
H15B H 0.671152 -0.254165 0.292156 0.047 Uiso 1 1 calc R U . . .
C16 C 1.2312(14) -0.0273(14) 0.4047(7) 0.041(3) Uani 1 1 d . . . . .
C13 C 1.0847(13) -0.0415(12) 0.3424(7) 0.037(2) Uani 1 1 d . . . . .
H13 H 1.123642 -0.055001 0.287832 0.044 Uiso 1 1 calc R U . . .
C10 C 0.7331(14) -0.0562(13) 0.2902(7) 0.040(3) Uani 1 1 d . . . . .
H10 H 0.649512 -0.068667 0.243623 0.047 Uiso 1 1 calc R U . . .
C9 C 0.6484(14) -0.0349(12) 0.3700(7) 0.038(3) Uani 1 1 d . . . . .
C11 C 0.8961(16) 0.0658(14) 0.2828(8) 0.044(3) Uani 1 1 d . . . . .
H11A H 0.933378 0.056551 0.228037 0.053 Uiso 1 1 calc R U . . .
H11B H 0.869371 0.144217 0.290757 0.053 Uiso 1 1 calc R U . . .
C12 C 1.0425(15) 0.0809(12) 0.3472(9) 0.044(3) Uani 1 1 d . . . . .
H12A H 1.145298 0.155189 0.339347 0.052 Uiso 1 1 calc R U . . .
H12B H 1.009297 0.100220 0.401686 0.052 Uiso 1 1 calc R U . . .
O9 O 0.0572(7) 0.1081(7) 0.4988(3) 0.0184(14) Uani 1 1 d . . . . .
O10 O 0.499(3) 0.747(4) 0.7421(15) 0.40(9) Uani 0.5 1 d . . P . .
C22A C 0.717(6) 0.882(4) -0.060(3) 0.085(11) Uiso 0.51(3) 1 d . . P B 2
C21A C 1.01(2) 1.054(12) -0.116(9) 0.61(9) Uiso 0.51(3) 1 d . . P B 2
C23A C 2(35) 2(35) -2(35) 0(35) Uiso 0.000(13) 1 d . . P A 2
C20A C 0.764(5) 1.125(4) 0.018(2) 0.078(11) Uiso 0.5 1 d . . P B 2


_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
N2 C23 1.49(4) . ?
N2 C27 1.08(3) . ?
N2 Zn1 2.19(3) . ?
N2 C23A 56(10) . ?
C23 H23 0.9300 . ?
C23 C24 1.81(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.13(3) . ?
C25 C26 1.33(2) . ?
C26 H26 0.9300 . ?
C26 C27 1.39(2) . ?
C27 H27 0.9300 . ?
N1 C18 1.3900 . ?
N1 C22 1.3900 . ?
N1 Zn2 2.072(7) . ?
N1 C22A 1.14(4) . ?
C18 C19 1.3900 . ?
C19 C20 1.3900 . ?
C19 C20A 1.11(4) . ?
C20 C21 1.3900 . ?
C21 C22 1.3900 . ?
C22 H22 0.9300 . ?
Zn2 Zn2 2.9108(17) 2_665 ?
Zn2 O3 2.029(8) 1_455 ?
Zn2 O4 2.035(7) 2_765 ?
Zn2 O1 2.054(8) . ?
Zn2 O2 2.060(8) 2_665 ?
Zn1 Zn1 2.903(2) 2_656 ?
Zn1 O7 2.051(9) 2_756 ?
Zn1 O6 2.047(9) 2_656 ?
Zn1 O5 2.034(9) . ?
Zn1 O8 2.051(10) 1_455 ?
O3 C8 1.244(13) . ?
O4 C8 1.245(13) . ?
O1 C1 1.260(14) . ?
O2 C1 1.247(14) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.531(13) . ?
C3 C2 1.523(12) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.535(14) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C2 1.537(13) . ?
C7 C6 1.527(13) . ?
C1 C2 1.535(11) . ?
C8 C5 1.547(11) . ?
C2 H2 0.9800 . ?
C5 H5 0.9800 . ?
C5 C6 1.518(15) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
O7 C16 1.225(17) . ?
O6 C9 1.211(16) . ?
O5 C9 1.224(16) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.530(17) . ?
C14 C13 1.544(16) . ?
O8 C16 1.283(17) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C10 1.525(17) . ?
C16 C13 1.519(14) . ?
C13 H13 0.9800 . ?
C13 C12 1.518(16) . ?
C10 H10 0.9800 . ?
C10 C9 1.549(15) . ?
C10 C11 1.542(17) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.538(17) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

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
C23 N2 Zn1 105.3(17) . . ?
C27 N2 C23 128(3) . . ?
C27 N2 Zn1 124(2) . . ?
C27 N2 C23A 117(10) . . ?
C23A N2 Zn1 118(10) . . ?
N2 C23 H23 127.0 . . ?
C24 C23 N2 106(2) . . ?
C24 C23 H23 126.6 . . ?
C23 C24 H24 126.7 . . ?
C25 C24 C23 106(2) . . ?
C25 C24 H24 126.8 . . ?
C24 C25 C26 136.1(17) . . ?
C25 C26 H26 121.7 . . ?
C25 C26 C27 116.5(18) . . ?
C27 C26 H26 121.8 . . ?
N2 C27 C26 122(2) . . ?
N2 C27 H27 119.1 . . ?
C26 C27 H27 118.7 . . ?
C18 N1 C22 120.0 . . ?
C18 N1 Zn2 118.8(6) . . ?
C22 N1 Zn2 121.2(6) . . ?
C22A N1 C18 119(2) . . ?
C22A N1 Zn2 119(2) . . ?
N1 C18 C19 120.0 . . ?
C20 C19 C18 120.0 . . ?
C20A C19 C18 133(2) . . ?
C19 C20 C21 120.0 . . ?
C22 C21 C20 120.0 . . ?
N1 C22 H22 120.0 . . ?
C21 C22 N1 120.0 . . ?
C21 C22 H22 120.0 . . ?
N1 Zn2 Zn2 179.8(2) . 2_665 ?
O3 Zn2 N1 100.0(3) 1_455 . ?
O3 Zn2 Zn2 80.1(3) 1_455 2_665 ?
O3 Zn2 O4 160.0(4) 1_455 2_765 ?
O3 Zn2 O1 88.6(4) 1_455 . ?
O3 Zn2 O2 89.4(4) 1_455 2_665 ?
O4 Zn2 N1 100.0(4) 2_765 . ?
O4 Zn2 Zn2 79.9(3) 2_765 2_665 ?
O4 Zn2 O1 88.3(4) 2_765 . ?
O4 Zn2 O2 87.2(4) 2_765 2_665 ?
O1 Zn2 N1 99.2(4) . . ?
O1 Zn2 Zn2 80.6(3) . 2_665 ?
O1 Zn2 O2 161.3(5) . 2_665 ?
O2 Zn2 N1 99.5(4) 2_665 . ?
O2 Zn2 Zn2 80.7(3) 2_665 2_665 ?
N2 Zn1 Zn1 173.3(7) . 2_656 ?
O7 Zn1 N2 102.4(7) 2_756 . ?
O7 Zn1 Zn1 80.3(4) 2_756 2_656 ?
O7 Zn1 O6 87.5(5) 2_756 2_656 ?
O7 Zn1 O8 161.0(6) 2_756 1_455 ?
O6 Zn1 N2 95.1(8) 2_656 . ?
O6 Zn1 Zn1 78.8(3) 2_656 2_656 ?
O6 Zn1 O8 89.6(5) 2_656 1_455 ?
O5 Zn1 N2 106.1(9) . . ?
O5 Zn1 Zn1 80.0(3) . 2_656 ?
O5 Zn1 O7 88.7(5) . 2_756 ?
O5 Zn1 O6 158.8(5) . 2_656 ?
O5 Zn1 O8 87.2(5) . 1_455 ?
O8 Zn1 N2 96.6(8) 1_455 . ?
O8 Zn1 Zn1 80.7(4) 1_455 2_656 ?
C8 O3 Zn2 127.6(7) . 1_655 ?
C8 O4 Zn2 127.5(7) . 2_765 ?
C1 O1 Zn2 125.7(8) . . ?
C1 O2 Zn2 125.6(8) . 2_665 ?
H3A C3 H3B 107.9 . . ?
C4 C3 H3A 109.2 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
C2 C3 C4 111.9(8) . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.3 . . ?
C3 C4 C5 111.2(8) . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C2 C7 H7A 109.4 . . ?
C2 C7 H7B 109.3 . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.3 . . ?
C6 C7 C2 111.4(8) . . ?
O1 C1 C2 115.8(9) . . ?
O2 C1 O1 127.1(10) . . ?
O2 C1 C2 117.1(9) . . ?
O3 C8 C5 118.1(9) . . ?
O4 C8 O3 124.9(9) . . ?
O4 C8 C5 117.0(9) . . ?
C3 C2 C7 111.3(7) . . ?
C3 C2 C1 113.0(8) . . ?
C3 C2 H2 106.8 . . ?
C7 C2 C1 111.7(7) . . ?
C7 C2 H2 106.8 . . ?
C1 C2 H2 106.8 . . ?
C4 C5 C8 112.1(8) . . ?
C4 C5 H5 107.3 . . ?
C8 C5 H5 107.3 . . ?
C6 C5 C4 110.8(8) . . ?
C6 C5 C8 111.8(8) . . ?
C6 C5 H5 107.3 . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.3 . . ?
C5 C6 C7 111.9(8) . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
C16 O7 Zn1 127.5(10) . 2_756 ?
C9 O6 Zn1 128.9(9) . 2_656 ?
C9 O5 Zn1 127.8(9) . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C15 C14 C13 112.1(10) . . ?
C13 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
C16 O8 Zn1 125.8(10) . 1_655 ?
C14 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C10 C15 C14 112.1(9) . . ?
C10 C15 H15A 109.1 . . ?
C10 C15 H15B 109.2 . . ?
O7 C16 O8 125.1(12) . . ?
O7 C16 C13 119.1(12) . . ?
O8 C16 C13 115.8(12) . . ?
C14 C13 H13 106.6 . . ?
C16 C13 C14 112.0(10) . . ?
C16 C13 H13 106.6 . . ?
C16 C13 C12 113.6(10) . . ?
C12 C13 C14 110.8(9) . . ?
C12 C13 H13 106.7 . . ?
C15 C10 H10 107.5 . . ?
C15 C10 C9 111.8(10) . . ?
C15 C10 C11 110.9(10) . . ?
C9 C10 H10 107.4 . . ?
C9 C10 C11 111.5(10) . . ?
C11 C10 H10 107.5 . . ?
O6 C9 O5 124.3(12) . . ?
O6 C9 C10 118.2(12) . . ?
O5 C9 C10 117.3(12) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 C10 110.5(10) . . ?
C12 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C13 C12 C11 112.9(10) . . ?
C13 C12 H12A 108.9 . . ?
C13 C12 H12B 109.0 . . ?
C11 C12 H12A 108.9 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1136Ex_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1912779'
loop_
_audit_author_name
_audit_author_address
'Mohammad Mir'
;Aliah University
India
;
_audit_update_record             
;
2019-04-29 deposited with the CCDC.	2019-09-18 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         'C19 H19 N O4 Zn'
_chemical_formula_sum            'C19 H19 N O4 Zn'
_chemical_formula_weight         390.74

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5614(3)
_cell_length_b                   9.3895(3)
_cell_length_c                   11.0353(3)
_cell_angle_alpha                83.8490(10)
_cell_angle_beta                 84.6820(10)
_cell_angle_gamma                81.1340(10)
_cell_volume                     868.83(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    8412
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      26.25

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   0.756
_exptl_transmission_factor_max   0.982
_exptl_crystal_size_max          0.185
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.012
_exptl_absorpt_coefficient_mu    1.436
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Mo
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13037
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.415
_diffrn_reflns_theta_max         26.262
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3506
_reflns_number_gt                2999
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.1000P)²+0.0260P] 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         3506
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.1238
_refine_ls_wR_factor_gt          0.1084
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_restrained_S_all      0.942
_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 0.02586(3) 0.40305(3) 0.90385(3) 0.03127(15) Uani 1 1 d . . . . .
O1 O 0.2085(2) 0.5161(2) 0.8578(2) 0.0476(5) Uani 1 1 d . . . . .
O3 O 0.8808(3) 0.5565(2) 0.8040(2) 0.0521(6) Uani 1 1 d . . . . .
O2 O 0.1727(3) 0.6607(3) 1.0070(2) 0.0551(6) Uani 1 1 d . . . . .
O4 O 0.8541(3) 0.7015(3) 0.9509(2) 0.0566(6) Uani 1 1 d . . . . .
N1 N 0.0862(3) 0.2385(3) 0.7942(2) 0.0365(5) Uani 1 1 d . . . . .
C13 C 0.3762(3) 0.6972(3) 0.8495(3) 0.0337(6) Uani 1 1 d . . . . .
H13 H 0.325080 0.777654 0.796075 0.040 Uiso 1 1 calc R U . . .
C12 C 0.2429(3) 0.6174(3) 0.9099(2) 0.0340(6) Uani 1 1 d . . . . .
C19 C 0.8188(3) 0.6680(3) 0.8524(3) 0.0356(6) Uani 1 1 d . . . . .
C15 C 0.6111(3) 0.7006(4) 0.6970(3) 0.0431(7) Uani 1 1 d . . . . .
H15A H 0.554162 0.773802 0.641956 0.052 Uiso 1 1 calc R U . . .
H15B H 0.689295 0.640403 0.648030 0.052 Uiso 1 1 calc R U . . .
C16 C 0.6954(3) 0.7743(3) 0.7833(3) 0.0391(7) Uani 1 1 d . . . . .
H16 H 0.753155 0.844277 0.732524 0.047 Uiso 1 1 calc R U . . .
C14 C 0.4955(3) 0.6078(3) 0.7664(3) 0.0369(6) Uani 1 1 d . . . . .
H14A H 0.553507 0.528376 0.815049 0.044 Uiso 1 1 calc R U . . .
H14B H 0.439844 0.567211 0.708788 0.044 Uiso 1 1 calc R U . . .
C18 C 0.4600(4) 0.7664(3) 0.9390(3) 0.0436(7) Uani 1 1 d . . . . .
H18A H 0.516749 0.691421 0.992628 0.052 Uiso 1 1 calc R U . . .
H18B H 0.382145 0.825617 0.989036 0.052 Uiso 1 1 calc R U . . .
C3 C 0.1595(3) 0.0111(3) 0.6426(2) 0.0332(6) Uani 1 1 d . . . . .
C6 C 0.1943(3) -0.1046(3) 0.5592(3) 0.0357(6) Uani 1 1 d . . . . .
C17 C 0.5764(4) 0.8602(3) 0.8696(3) 0.0505(8) Uani 1 1 d . . . . .
H17A H 0.517758 0.941075 0.822799 0.061 Uiso 1 1 calc R U . . .
H17B H 0.632935 0.899075 0.927682 0.061 Uiso 1 1 calc R U . . .
C4 C 0.0613(4) 0.0020(3) 0.7474(3) 0.0475(8) Uani 1 1 d . . . . .
H4 H 0.017018 -0.082181 0.770508 0.057 Uiso 1 1 calc R U . . .
C5 C 0.0272(4) 0.1156(3) 0.8191(3) 0.0497(8) Uani 1 1 d . . . . .
H5 H -0.041145 0.105434 0.889037 0.060 Uiso 1 1 calc R U . . .
C7 C 0.2957(5) -0.0923(4) 0.4545(3) 0.0533(8) Uani 1 1 d . . . . .
H7 H 0.347851 -0.011660 0.438490 0.064 Uiso 1 1 calc R U . . .
C1 C 0.1878(5) 0.2459(4) 0.6963(3) 0.0681(11) Uani 1 1 d . . . . .
H1 H 0.236012 0.328765 0.678899 0.082 Uiso 1 1 calc R U . . .
C2 C 0.2260(5) 0.1384(4) 0.6194(3) 0.0716(13) Uani 1 1 d . . . . .
H2 H 0.296713 0.150571 0.551153 0.086 Uiso 1 1 calc R U . . .
C8 C 0.3207(6) -0.1968(4) 0.3739(3) 0.0721(11) Uani 1 1 d . . . . .
H8 H 0.388644 -0.185586 0.303864 0.086 Uiso 1 1 calc R U . . .
C9 C 0.2465(5) -0.3172(4) 0.3957(4) 0.0705(11) Uani 1 1 d . . . . .
H9 H 0.261519 -0.386848 0.340231 0.085 Uiso 1 1 calc R U . . .
C11 C 0.1251(5) -0.2295(4) 0.5813(4) 0.0634(10) Uani 1 1 d . . . . .
H11 H 0.060109 -0.243781 0.652537 0.076 Uiso 1 1 calc R U . . .
C10 C 0.1508(5) -0.3328(4) 0.4997(5) 0.0800(13) Uani 1 1 d . . . . .
H10 H 0.101593 -0.415218 0.516145 0.096 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 O1 2.0199(19) . ?
Zn1 O2 2.023(2) 2_567 ?
Zn1 N1 2.039(2) . ?
Zn1 O3 2.048(2) 1_455 ?
Zn1 O4 2.061(2) 2_667 ?
Zn1 Zn1 2.9017(6) 2_567 ?
O1 C12 1.248(3) . ?
O3 C19 1.249(4) . ?
O2 C12 1.254(3) . ?
O4 C19 1.239(4) . ?
N1 C5 1.321(4) . ?
N1 C1 1.326(4) . ?
C13 C14 1.522(4) . ?
C13 C12 1.525(4) . ?
C13 C18 1.525(4) . ?
C13 H13 0.9800 . ?
C19 C16 1.534(4) . ?
C15 C14 1.519(4) . ?
C15 C16 1.527(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.525(5) . ?
C16 H16 0.9800 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C18 C17 1.530(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C3 C4 1.368(4) . ?
C3 C2 1.391(4) . ?
C3 C6 1.477(4) . ?
C6 C11 1.383(4) . ?
C6 C7 1.385(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C4 C5 1.375(4) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C7 C8 1.373(5) . ?
C7 H7 0.9300 . ?
C1 C2 1.370(5) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C8 C9 1.369(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.355(6) . ?
C9 H9 0.9300 . ?
C11 C10 1.373(5) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?

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
O1 Zn1 O2 160.37(10) . 2_567 ?
O1 Zn1 N1 100.63(9) . . ?
O2 Zn1 N1 98.83(9) 2_567 . ?
O1 Zn1 O3 90.18(9) . 1_455 ?
O2 Zn1 O3 87.45(10) 2_567 1_455 ?
N1 Zn1 O3 104.45(9) . 1_455 ?
O1 Zn1 O4 88.62(10) . 2_667 ?
O2 Zn1 O4 87.03(11) 2_567 2_667 ?
N1 Zn1 O4 95.34(10) . 2_667 ?
O3 Zn1 O4 160.05(10) 1_455 2_667 ?
O1 Zn1 Zn1 80.19(6) . 2_567 ?
O2 Zn1 Zn1 80.24(7) 2_567 2_567 ?
N1 Zn1 Zn1 168.39(7) . 2_567 ?
O3 Zn1 Zn1 87.09(7) 1_455 2_567 ?
O4 Zn1 Zn1 73.08(7) 2_667 2_567 ?
C12 O1 Zn1 127.60(19) . . ?
C19 O3 Zn1 118.3(2) . 1_655 ?
C12 O2 Zn1 127.1(2) . 2_567 ?
C19 O4 Zn1 136.0(2) . 2_667 ?
C5 N1 C1 116.0(3) . . ?
C5 N1 Zn1 121.1(2) . . ?
C1 N1 Zn1 122.9(2) . . ?
C14 C13 C12 114.0(2) . . ?
C14 C13 C18 110.9(2) . . ?
C12 C13 C18 113.8(2) . . ?
C14 C13 H13 105.7 . . ?
C12 C13 H13 105.7 . . ?
C18 C13 H13 105.7 . . ?
O1 C12 O2 124.6(3) . . ?
O1 C12 C13 117.8(2) . . ?
O2 C12 C13 117.6(3) . . ?
O4 C19 O3 124.4(3) . . ?
O4 C19 C16 117.4(3) . . ?
O3 C19 C16 118.2(3) . . ?
C14 C15 C16 111.7(2) . . ?
C14 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
C17 C16 C15 111.1(2) . . ?
C17 C16 C19 112.2(3) . . ?
C15 C16 C19 112.6(2) . . ?
C17 C16 H16 106.9 . . ?
C15 C16 H16 106.9 . . ?
C19 C16 H16 106.9 . . ?
C15 C14 C13 110.7(2) . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C13 C18 C17 110.3(3) . . ?
C13 C18 H18A 109.6 . . ?
C17 C18 H18A 109.6 . . ?
C13 C18 H18B 109.6 . . ?
C17 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
C4 C3 C2 115.2(3) . . ?
C4 C3 C6 123.2(3) . . ?
C2 C3 C6 121.6(3) . . ?
C11 C6 C7 116.9(3) . . ?
C11 C6 C3 121.4(3) . . ?
C7 C6 C3 121.6(3) . . ?
C16 C17 C18 111.8(2) . . ?
C16 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
N1 C5 C4 123.7(3) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
C8 C7 C6 121.3(3) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
N1 C1 C2 123.7(3) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C1 C2 C3 120.4(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C9 C8 C7 120.6(4) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C10 C9 C8 118.7(3) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C10 C11 C6 121.1(4) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
C9 C10 C11 121.3(4) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?

_refine_diff_density_max         0.440
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.167

