# 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_xu7
_database_code_depnum_ccdc_archive 'CCDC 1878515'
loop_
_audit_author_name
_audit_author_address
Xu-1
;NingXiaUniversity
China
;
_audit_update_record             
;
2018-11-12 deposited with the CCDC.	2019-02-19 downloaded from the CCDC.
;
_audit_creation_date             2017-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 N O5 Zn'
_chemical_formula_sum            'C13 H9 N O5 Zn'
_chemical_formula_weight         324.58
_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   6.49204(13)
_cell_length_b                   18.1324(3)
_cell_length_c                   10.4567(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.4564(19)
_cell_angle_gamma                90
_cell_volume                     1214.20(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2510
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.2900
_cell_measurement_theta_min      4.8700
_shelx_estimated_absorpt_T_max   0.644
_shelx_estimated_absorpt_T_min   0.613
_exptl_absorpt_coefficient_mu    3.017
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51060
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3594
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        65.905
_diffrn_reflns_theta_max         65.905
_diffrn_reflns_theta_min         4.878
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6525
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     84.00 175.00   1.00    1.00    --  106.40  30.00 -60.00   91
  2  ω    101.00 178.00   1.00    1.00    --  106.40 125.00-150.00   77
  3  ω     86.00 177.00   1.00    1.00    --  106.40  77.00   0.00   91
  4  ω     38.00 129.00   1.00    1.00    --  106.40 -61.00-120.00   91
  5  ω   -114.00 -23.00   1.00    1.00    --  -41.14 -38.00-120.00   91
  6  ω   -125.00 -35.00   1.00    1.00    --  -41.14 178.00 -30.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0922399000
_diffrn_orient_matrix_UB_12      0.0547934000
_diffrn_orient_matrix_UB_13      0.1067695000
_diffrn_orient_matrix_UB_21      -0.0398845000
_diffrn_orient_matrix_UB_22      -0.0557486000
_diffrn_orient_matrix_UB_23      0.1043752000
_diffrn_orient_matrix_UB_31      0.2186844000
_diffrn_orient_matrix_UB_32      -0.0332531000
_diffrn_orient_matrix_UB_33      0.0009559000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1982
_reflns_number_total             2104
_reflns_odcompleteness_completeness 99.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.723
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2104
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.084
_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)+(0.0659P)²+0.8791P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.0996
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Rotating group:
 O1W(H1WA,H1WB)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11), C4(H4), C13(H13), C12(H12), C3(H3), C10(H10)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.14105(5) 0.44414(2) 0.19246(3) 0.01133(16) Uani 1 1 d . . . . .
O1 O -0.0378(3) 0.35805(10) 0.14664(18) 0.0178(4) Uani 1 1 d . . . . .
O1W O 0.2615(3) 0.45958(10) 0.03127(17) 0.0168(4) Uani 1 1 d . . . . .
H1WA H 0.3860 0.4405 0.0387 0.025 Uiso 1 1 d GR . . . .
H1WB H 0.2833 0.5063 0.0196 0.025 Uiso 1 1 d GR . . . .
N1 N -1.1217(3) 0.10169(12) -0.1800(2) 0.0134(4) Uani 1 1 d . . . . .
O3 O -0.4644(3) 0.01600(10) 0.23720(18) 0.0219(4) Uani 1 1 d . . . . .
O2 O -0.3453(3) 0.40354(9) 0.05125(17) 0.0173(4) Uani 1 1 d . . . . .
C1 C -0.2330(4) 0.35344(13) 0.1063(2) 0.0122(5) Uani 1 1 d . . . . .
C7 C -0.5191(4) 0.25774(13) 0.0610(2) 0.0127(5) Uani 1 1 d . . . . .
H7 H -0.5957 0.2902 0.0029 0.015 Uiso 1 1 calc R . . . .
C11 C -0.9450(4) 0.06246(14) -0.1462(3) 0.0159(5) Uani 1 1 d . . . . .
H11 H -0.9364 0.0155 -0.1807 0.019 Uiso 1 1 calc R . . . .
O4 O -0.7657(3) 0.07272(11) 0.2398(2) 0.0260(5) Uani 1 1 d . . . . .
C4 C -0.2921(4) 0.16251(15) 0.2383(3) 0.0183(6) Uani 1 1 d . . . . .
H4 H -0.2153 0.1306 0.2975 0.022 Uiso 1 1 calc R . . . .
C8 C -0.5835(4) 0.07229(15) 0.2188(2) 0.0178(6) Uani 1 1 d . . . . .
C2 C -0.3250(4) 0.27943(13) 0.1282(2) 0.0123(5) Uani 1 1 d . . . . .
C5 C -0.4889(4) 0.14154(14) 0.1749(2) 0.0150(5) Uani 1 1 d . . . . .
C6 C -0.6000(4) 0.18802(13) 0.0797(2) 0.0126(5) Uani 1 1 d . . . . .
C13 C -0.9666(4) 0.20047(14) -0.0460(3) 0.0162(5) Uani 1 1 d . . . . .
H13 H -0.9776 0.2481 -0.0146 0.019 Uiso 1 1 calc R . . . .
C12 C -1.1297(4) 0.16983(14) -0.1305(3) 0.0172(5) Uani 1 1 d . . . . .
H12 H -1.2505 0.1975 -0.1543 0.021 Uiso 1 1 calc R . . . .
C9 C -0.7856(4) 0.15953(14) -0.0082(2) 0.0133(5) Uani 1 1 d . . . . .
C3 C -0.2104(4) 0.23032(14) 0.2137(3) 0.0170(5) Uani 1 1 d . . . . .
H3 H -0.0772 0.2432 0.2547 0.020 Uiso 1 1 calc R . . . .
C10 C -0.7769(4) 0.08970(14) -0.0624(3) 0.0165(5) Uani 1 1 d . . . . .
H10 H -0.6567 0.0613 -0.0417 0.020 Uiso 1 1 calc R . . . .


_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 1.9576(17) . ?
Zn1 O1W 1.9912(18) . ?
Zn1 N1 2.041(2) 4_766 ?
Zn1 O3 1.9574(19) 2_455 ?
Zn1 C8 2.552(3) 2_455 ?
O1 C1 1.271(3) . ?
N1 Zn1 2.041(2) 4_465 ?
N1 C11 1.347(3) . ?
N1 C12 1.344(3) . ?
O3 Zn1 1.9575(19) 2_445 ?
O3 C8 1.276(3) . ?
O2 C1 1.245(3) . ?
C1 C2 1.502(3) . ?
C7 C2 1.395(3) . ?
C7 C6 1.395(3) . ?
C11 C10 1.375(4) . ?
O4 C8 1.238(4) . ?
C4 C5 1.392(4) . ?
C4 C3 1.380(4) . ?
C8 Zn1 2.552(3) 2_445 ?
C8 C5 1.503(3) . ?
C2 C3 1.388(4) . ?
C5 C6 1.409(4) . ?
C6 C9 1.483(3) . ?
C13 C12 1.380(4) . ?
C13 C9 1.392(3) . ?
C9 C10 1.392(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
O1 Zn1 O1W 101.81(8) . . ?
O1 Zn1 N1 100.89(8) . 4_766 ?
O1 Zn1 C8 134.32(8) . 2_455 ?
O1W Zn1 N1 104.54(8) . 4_766 ?
O1W Zn1 C8 106.31(8) . 2_455 ?
N1 Zn1 C8 105.85(8) 4_766 2_455 ?
O3 Zn1 O1 105.20(8) 2_455 . ?
O3 Zn1 O1W 124.08(8) 2_455 . ?
O3 Zn1 N1 116.83(8) 2_455 4_766 ?
O3 Zn1 C8 29.25(9) 2_455 2_455 ?
C1 O1 Zn1 130.75(16) . . ?
C11 N1 Zn1 118.37(17) . 4_465 ?
C12 N1 Zn1 123.58(17) . 4_465 ?
C12 N1 C11 118.0(2) . . ?
C8 O3 Zn1 102.19(17) . 2_445 ?
O1 C1 C2 114.1(2) . . ?
O2 C1 O1 125.6(2) . . ?
O2 C1 C2 120.3(2) . . ?
C2 C7 C6 121.0(2) . . ?
N1 C11 C10 122.0(2) . . ?
C3 C4 C5 120.3(2) . . ?
O3 C8 Zn1 48.56(13) . 2_445 ?
O3 C8 C5 116.5(2) . . ?
O4 C8 Zn1 74.93(15) . 2_445 ?
O4 C8 O3 123.5(2) . . ?
O4 C8 C5 120.0(2) . . ?
C5 C8 Zn1 164.49(19) . 2_445 ?
C7 C2 C1 121.6(2) . . ?
C3 C2 C1 119.1(2) . . ?
C3 C2 C7 119.2(2) . . ?
C4 C5 C8 118.2(2) . . ?
C4 C5 C6 119.8(2) . . ?
C6 C5 C8 121.9(2) . . ?
C7 C6 C5 118.7(2) . . ?
C7 C6 C9 121.0(2) . . ?
C5 C6 C9 119.9(2) . . ?
C12 C13 C9 119.4(2) . . ?
N1 C12 C13 122.9(2) . . ?
C13 C9 C6 123.5(2) . . ?
C13 C9 C10 117.3(2) . . ?
C10 C9 C6 119.1(2) . . ?
C4 C3 C2 120.7(2) . . ?
C11 C10 C9 120.4(2) . . ?

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 O1 C1 O2 22.4(4) . . . . ?
Zn1 O1 C1 C2 -158.54(17) . . . . ?
Zn1 N1 C11 C10 179.1(2) 4_465 . . . ?
Zn1 N1 C12 C13 -178.9(2) 4_465 . . . ?
Zn1 O3 C8 O4 -2.4(3) 2_445 . . . ?
Zn1 O3 C8 C5 174.89(17) 2_445 . . . ?
Zn1 C8 C5 C4 -31.4(8) 2_445 . . . ?
Zn1 C8 C5 C6 153.8(6) 2_445 . . . ?
O1 C1 C2 C7 -162.4(2) . . . . ?
O1 C1 C2 C3 15.0(3) . . . . ?
N1 C11 C10 C9 0.6(4) . . . . ?
O3 C8 C5 C4 -45.8(3) . . . . ?
O3 C8 C5 C6 139.4(3) . . . . ?
O2 C1 C2 C7 16.7(4) . . . . ?
O2 C1 C2 C3 -165.9(2) . . . . ?
C1 C2 C3 C4 178.6(2) . . . . ?
C7 C2 C3 C4 -4.0(4) . . . . ?
C7 C6 C9 C13 -47.0(4) . . . . ?
C7 C6 C9 C10 129.4(3) . . . . ?
C11 N1 C12 C13 -0.9(4) . . . . ?
O4 C8 C5 C4 131.6(3) . . . . ?
O4 C8 C5 C6 -43.2(4) . . . . ?
C4 C5 C6 C7 -6.6(4) . . . . ?
C4 C5 C6 C9 166.4(2) . . . . ?
C8 C5 C6 C7 168.1(2) . . . . ?
C8 C5 C6 C9 -18.9(4) . . . . ?
C2 C7 C6 C5 4.5(4) . . . . ?
C2 C7 C6 C9 -168.5(2) . . . . ?
C5 C4 C3 C2 1.8(4) . . . . ?
C5 C6 C9 C13 140.2(3) . . . . ?
C5 C6 C9 C10 -43.4(3) . . . . ?
C6 C7 C2 C1 178.2(2) . . . . ?
C6 C7 C2 C3 0.8(4) . . . . ?
C6 C9 C10 C11 -178.7(2) . . . . ?
C13 C9 C10 C11 -2.1(4) . . . . ?
C12 N1 C11 C10 0.9(4) . . . . ?
C12 C13 C9 C6 178.6(2) . . . . ?
C12 C13 C9 C10 2.2(4) . . . . ?
C9 C13 C12 N1 -0.7(4) . . . . ?
C3 C4 C5 C8 -171.3(2) . . . . ?
C3 C4 C5 C6 3.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.879
_oxdiff_exptl_absorpt_empirical_full_min 0.505
####################################################################### 
# 
# 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_ww
_database_code_depnum_ccdc_archive 'CCDC 1878750'
loop_
_audit_author_name
_audit_author_address
Xu-3
;NingXiaUniversity
China
;
_audit_update_record             
;
2018-11-13 deposited with the CCDC.	2019-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H9 Cd N O5'
_chemical_formula_weight         371.61

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'

_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                   8.3739(5)
_cell_length_b                   6.8579(4)
_cell_length_c                   21.1309(13)
_cell_angle_alpha                90
_cell_angle_beta                 94.9690(10)
_cell_angle_gamma                90
_cell_volume                     1208.93(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3050
_cell_measurement_theta_min      2.7030
_cell_measurement_theta_max      27.5565

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.042
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    1.825
_shelx_estimated_absorpt_T_min   0.700
_shelx_estimated_absorpt_T_max   0.723
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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-CCd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5863
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.703
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_full        25.009
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2115
_reflns_number_gt                1905
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0216P)²+0.5263P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2115
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0240
_refine_ls_R_factor_gt           0.0197
_refine_ls_wR_factor_ref         0.0462
_refine_ls_wR_factor_gt          0.0445
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.014
_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
N1 N 1.4721(3) 0.8086(3) 0.28351(10) 0.0112(5) Uani 1 1 d . . . . .
Cd1 Cd 0.83315(2) 0.28094(3) 0.28613(2) 0.00864(8) Uani 1 1 d . . . . .
C1 C 0.8839(3) 0.7689(4) 0.32190(13) 0.0104(6) Uani 1 1 d . . . . .
C2 C 0.9437(3) 0.7561(4) 0.39066(12) 0.0076(5) Uani 1 1 d . . . . .
C3 C 0.8300(3) 0.7273(4) 0.43426(12) 0.0102(6) Uani 1 1 d . . . . .
H3 H 0.7207 0.7085 0.4194 0.012 Uiso 1 1 calc R U . . .
C4 C 0.8746(3) 0.7259(4) 0.49872(13) 0.0098(6) Uani 1 1 d . . . . .
H4 H 0.7962 0.7063 0.5280 0.012 Uiso 1 1 calc R U . . .
C5 C 1.0342(3) 0.7531(4) 0.52065(12) 0.0092(6) Uani 1 1 d . . . . .
C6 C 1.1485(3) 0.7826(4) 0.47790(12) 0.0097(6) Uani 1 1 d . . . . .
H6 H 1.2574 0.8018 0.4932 0.012 Uiso 1 1 calc R U . . .
C7 C 1.1054(3) 0.7844(4) 0.41242(12) 0.0088(5) Uani 1 1 d . . . . .
C8 C 1.0814(3) 0.7428(4) 0.59082(13) 0.0102(6) Uani 1 1 d . . . . .
C9 C 1.2313(3) 0.7976(4) 0.36752(12) 0.0091(5) Uani 1 1 d . . . . .
C10 C 1.3542(3) 0.9345(4) 0.37420(13) 0.0138(6) Uani 1 1 d . . . . .
H10 H 1.3579 1.0276 0.4076 0.017 Uiso 1 1 calc R U . . .
C11 C 1.4707(3) 0.9336(4) 0.33188(13) 0.0138(6) Uani 1 1 d . . . . .
H11 H 1.5545 1.0271 0.3375 0.017 Uiso 1 1 calc R U . . .
C12 C 1.3529(3) 0.6753(4) 0.27655(13) 0.0153(6) Uani 1 1 d . . . . .
H12 H 1.3513 0.5857 0.2422 0.018 Uiso 1 1 calc R U . . .
C13 C 1.2339(3) 0.6649(4) 0.31751(13) 0.0136(6) Uani 1 1 d . . . . .
H13 H 1.1534 0.5673 0.3117 0.016 Uiso 1 1 calc R U . . .
O1 O 0.8151(2) 0.6206(3) 0.29527(8) 0.0138(4) Uani 1 1 d . . . . .
O1W O 1.4855(3) 0.3912(5) 0.43938(14) 0.0530(8) Uani 1 1 d G . . . .
H1WA H 1.4194 0.4090 0.4058 0.080 Uiso 1 1 d G U . . .
H1WB H 1.5777 0.3526 0.4279 0.080 Uiso 1 1 d G U . . .
O2 O 0.8895(2) 0.9249(3) 0.29197(8) 0.0145(4) Uani 1 1 d . . . . .
O3 O 0.9734(2) 0.7208(3) 0.62771(8) 0.0125(4) Uani 1 1 d . . . . .
O4 O 1.2295(2) 0.7545(3) 0.61115(9) 0.0121(4) 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
N1 C11 1.335(3) . ?
N1 C12 1.352(3) . ?
N1 Cd1 2.297(2) 2_755 ?
Cd1 O4 2.2897(18) 3_766 ?
Cd1 N1 2.297(2) 2_745 ?
Cd1 O1 2.3107(18) 2_645 ?
Cd1 O3 2.3299(18) 3_766 ?
Cd1 O1 2.3436(19) . ?
Cd1 O2 2.4878(18) 1_545 ?
Cd1 O2 2.5774(19) 2_645 ?
Cd1 C8 2.641(3) 3_766 ?
C1 O2 1.246(3) . ?
C1 O1 1.275(3) . ?
C1 C2 1.498(4) . ?
C2 C3 1.395(4) . ?
C2 C7 1.405(4) . ?
C3 C4 1.381(4) . ?
C4 C5 1.388(4) . ?
C5 C6 1.387(4) . ?
C5 C8 1.503(4) . ?
C6 C7 1.399(4) . ?
C7 C9 1.481(4) . ?
C8 O3 1.253(3) . ?
C8 O4 1.279(3) . ?
C8 Cd1 2.641(3) 3_766 ?
C9 C10 1.391(4) . ?
C9 C13 1.396(4) . ?
C10 C11 1.379(4) . ?
C12 C13 1.378(4) . ?
O1 Cd1 2.3107(18) 2_655 ?
O2 Cd1 2.4877(18) 1_565 ?
O2 Cd1 2.5774(19) 2_655 ?
O3 Cd1 2.3298(18) 3_766 ?
O4 Cd1 2.2898(18) 3_766 ?

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
C11 N1 C12 117.5(2) . . ?
C11 N1 Cd1 126.67(18) . 2_755 ?
C12 N1 Cd1 115.64(17) . 2_755 ?
O4 Cd1 N1 148.17(7) 3_766 2_745 ?
O4 Cd1 O1 120.19(6) 3_766 2_645 ?
N1 Cd1 O1 85.87(7) 2_745 2_645 ?
O4 Cd1 O3 57.28(6) 3_766 3_766 ?
N1 Cd1 O3 90.97(7) 2_745 3_766 ?
O1 Cd1 O3 150.67(6) 2_645 3_766 ?
O4 Cd1 O1 90.32(6) 3_766 . ?
N1 Cd1 O1 91.43(7) 2_745 . ?
O1 Cd1 O1 120.00(5) 2_645 . ?
O3 Cd1 O1 89.19(6) 3_766 . ?
O4 Cd1 O2 84.66(6) 3_766 1_545 ?
N1 Cd1 O2 88.32(7) 2_745 1_545 ?
O1 Cd1 O2 69.97(6) 2_645 1_545 ?
O3 Cd1 O2 80.80(6) 3_766 1_545 ?
O1 Cd1 O2 169.98(6) . 1_545 ?
O4 Cd1 O2 115.80(6) 3_766 2_645 ?
N1 Cd1 O2 94.17(7) 2_745 2_645 ?
O1 Cd1 O2 52.65(6) 2_645 2_645 ?
O3 Cd1 O2 156.61(6) 3_766 2_645 ?
O1 Cd1 O2 67.90(6) . 2_645 ?
O2 Cd1 O2 122.11(5) 1_545 2_645 ?
O4 Cd1 C8 28.95(7) 3_766 3_766 ?
N1 Cd1 C8 119.27(8) 2_745 3_766 ?
O1 Cd1 C8 141.79(7) 2_645 3_766 ?
O3 Cd1 C8 28.32(7) 3_766 3_766 ?
O1 Cd1 C8 89.65(7) . 3_766 ?
O2 Cd1 C8 81.75(7) 1_545 3_766 ?
O2 Cd1 C8 140.63(7) 2_645 3_766 ?
O2 C1 O1 119.8(2) . . ?
O2 C1 C2 121.2(2) . . ?
O1 C1 C2 118.8(2) . . ?
C3 C2 C7 119.8(2) . . ?
C3 C2 C1 117.3(2) . . ?
C7 C2 C1 122.8(2) . . ?
C4 C3 C2 120.7(2) . . ?
C3 C4 C5 119.9(2) . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 C8 120.8(2) . . ?
C4 C5 C8 119.1(2) . . ?
C5 C6 C7 120.8(2) . . ?
C6 C7 C2 118.8(2) . . ?
C6 C7 C9 119.8(2) . . ?
C2 C7 C9 121.2(2) . . ?
O3 C8 O4 122.0(2) . . ?
O3 C8 C5 118.5(2) . . ?
O4 C8 C5 119.6(2) . . ?
O3 C8 Cd1 61.89(14) . 3_766 ?
O4 C8 Cd1 60.08(13) . 3_766 ?
C5 C8 Cd1 179.06(19) . 3_766 ?
C10 C9 C13 117.2(2) . . ?
C10 C9 C7 122.5(2) . . ?
C13 C9 C7 120.2(2) . . ?
C11 C10 C9 119.4(3) . . ?
N1 C11 C10 123.5(3) . . ?
N1 C12 C13 122.3(3) . . ?
C12 C13 C9 120.1(3) . . ?
C1 O1 Cd1 98.17(16) . 2_655 ?
C1 O1 Cd1 143.06(17) . . ?
Cd1 O1 Cd1 116.47(7) 2_655 . ?
C1 O2 Cd1 148.50(17) . 1_565 ?
C1 O2 Cd1 86.49(15) . 2_655 ?
Cd1 O2 Cd1 102.74(7) 1_565 2_655 ?
C8 O3 Cd1 89.79(16) . 3_766 ?
C8 O4 Cd1 90.96(15) . 3_766 ?

_refine_diff_density_max         0.418
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.080

####################################################################### 
# 
# 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_qq
_database_code_depnum_ccdc_archive 'CCDC 1878745'
loop_
_audit_author_name
_audit_author_address
Xu-2
;NingXiaUniversity
China
;
_audit_update_record             
;
2018-11-13 deposited with the CCDC.	2019-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H9 N O5 Zn'
_chemical_formula_weight         324.60

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'

_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                   21.9306(17)
_cell_length_b                   8.0884(2)
_cell_length_c                   17.009(2)
_cell_angle_alpha                90
_cell_angle_beta                 124.770(13)
_cell_angle_gamma                90
_cell_volume                     2478.4(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2520
_cell_measurement_theta_min      5.3540
_cell_measurement_theta_max      73.3870

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.740
_exptl_crystal_F_000             1312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    2.956
_shelx_estimated_absorpt_T_min   0.576
_shelx_estimated_absorpt_T_max   0.604
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  bruker-CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3298
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.910
_diffrn_reflns_theta_max         66.094
_diffrn_reflns_theta_full        66.094
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2140
_reflns_number_gt                2010
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0631P)²+12.9482P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2140
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1142
_refine_ls_wR_factor_gt          0.1128
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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 -0.24157(2) -0.07842(5) 0.33022(3) 0.01713(18) Uani 1 1 d . . . . .
O1 O -0.13352(13) 0.0220(3) 0.32237(17) 0.0255(5) Uani 1 1 d . . . . .
O2 O -0.16781(13) 0.0843(3) 0.41844(18) 0.0268(6) Uani 1 1 d . . . . .
O3 O 0.16848(12) 0.5277(3) 0.70208(16) 0.0198(5) Uani 1 1 d . . . . .
O4 O 0.21824(12) 0.3058(3) 0.68508(16) 0.0194(5) Uani 1 1 d . . . . .
N1W N 0.20158(15) 0.3716(4) 0.39114(19) 0.0183(6) Uani 1 1 d . . . . .
C1 C -0.12272(19) 0.0923(4) 0.3932(3) 0.0218(7) Uani 1 1 d . . . . .
C2 C -0.05164(17) 0.1877(4) 0.4592(2) 0.0179(7) Uani 1 1 d . . . . .
C3 C -0.03174(18) 0.2420(4) 0.5482(2) 0.0201(7) Uani 1 1 d . . . . .
H3 H -0.0647 0.2273 0.5671 0.024 Uiso 1 1 calc R U . . .
C4 C 0.03675(18) 0.3180(4) 0.6097(2) 0.0209(7) Uani 1 1 d . . . . .
H4 H 0.0498 0.3580 0.6700 0.025 Uiso 1 1 calc R U . . .
C5 C 0.08607(17) 0.3362(4) 0.5844(2) 0.0163(6) Uani 1 1 d . . . . .
C6 C 0.06550(17) 0.2870(4) 0.4927(2) 0.0158(6) Uani 1 1 d . . . . .
C7 C -0.00366(17) 0.2131(4) 0.4315(2) 0.0174(7) Uani 1 1 d . . . . .
H7 H -0.0184 0.1793 0.3695 0.021 Uiso 1 1 calc R U . . .
C8 C 0.16328(17) 0.3931(4) 0.6615(2) 0.0160(6) Uani 1 1 d . . . . .
C9 C 0.11361(17) 0.3159(4) 0.4589(2) 0.0159(6) Uani 1 1 d . . . . .
C10 C 0.15738(18) 0.4576(4) 0.4838(2) 0.0182(7) Uani 1 1 d . . . . .
H10 H 0.1573 0.5381 0.5244 0.022 Uiso 1 1 calc R U . . .
C11 C 0.20044(18) 0.4812(4) 0.4500(2) 0.0195(7) Uani 1 1 d . . . . .
H11 H 0.2304 0.5776 0.4685 0.023 Uiso 1 1 calc R U . . .
C12 C 0.15961(18) 0.2357(4) 0.3657(2) 0.0216(7) Uani 1 1 d . . . . .
H12 H 0.1599 0.1589 0.3237 0.026 Uiso 1 1 calc R U . . .
C13 C 0.11599(18) 0.2031(4) 0.3982(2) 0.0207(7) Uani 1 1 d . . . . .
H13 H 0.0876 0.1043 0.3796 0.025 Uiso 1 1 calc R U . . .
O1W O 0.3005(3) 0.3119(5) 0.1538(3) 0.0762(12) Uani 1 1 d . . . . .
H1 H 0.2676 0.2629 0.1569 0.114 Uiso 1 1 d R U . . .
H2 H 0.3331 0.3855 0.1987 0.114 Uiso 1 1 d 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 O2 1.958(2) . ?
Zn1 O4 1.966(2) 5_556 ?
Zn1 O3 1.976(2) 8_455 ?
Zn1 N1W 2.065(3) 3_445 ?
Zn1 O1 2.579(3) . ?
Zn1 C1 2.581(3) . ?
O1 C1 1.227(5) . ?
O2 C1 1.285(4) . ?
O3 C8 1.260(4) . ?
O3 Zn1 1.976(2) 8_556 ?
O4 C8 1.249(4) . ?
O4 Zn1 1.966(2) 5_556 ?
N1W C12 1.337(5) . ?
N1W C11 1.347(4) . ?
N1W Zn1 2.065(3) 3 ?
C1 C2 1.513(5) . ?
C2 C3 1.387(5) . ?
C2 C7 1.391(5) . ?
C3 C4 1.392(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.411(4) . ?
C5 C8 1.505(4) . ?
C6 C7 1.393(5) . ?
C6 C9 1.479(4) . ?
C7 H7 0.9500 . ?
C9 C10 1.397(5) . ?
C9 C13 1.400(5) . ?
C10 C11 1.371(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.377(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
O1W H1 0.8501 . ?
O1W H2 0.9084 . ?

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
O2 Zn1 O4 124.54(10) . 5_556 ?
O2 Zn1 O3 125.07(10) . 8_455 ?
O4 Zn1 O3 102.68(10) 5_556 8_455 ?
O2 Zn1 N1W 102.61(11) . 3_445 ?
O4 Zn1 N1W 99.24(11) 5_556 3_445 ?
O3 Zn1 N1W 94.90(10) 8_455 3_445 ?
O2 Zn1 O1 56.37(9) . . ?
O4 Zn1 O1 88.37(9) 5_556 . ?
O3 Zn1 O1 104.26(9) 8_455 . ?
N1W Zn1 O1 157.35(9) 3_445 . ?
O2 Zn1 C1 28.94(12) . . ?
O4 Zn1 C1 106.14(10) 5_556 . ?
O3 Zn1 C1 118.90(10) 8_455 . ?
N1W Zn1 C1 130.70(11) 3_445 . ?
O1 Zn1 C1 27.51(10) . . ?
C1 O1 Zn1 76.3(2) . . ?
C1 O2 Zn1 103.6(2) . . ?
C8 O3 Zn1 120.4(2) . 8_556 ?
C8 O4 Zn1 139.7(2) . 5_556 ?
C12 N1W C11 118.7(3) . . ?
C12 N1W Zn1 120.0(2) . 3 ?
C11 N1W Zn1 121.1(2) . 3 ?
O1 C1 O2 123.4(3) . . ?
O1 C1 C2 120.3(3) . . ?
O2 C1 C2 116.2(3) . . ?
O1 C1 Zn1 76.17(19) . . ?
O2 C1 Zn1 47.50(16) . . ?
C2 C1 Zn1 161.8(3) . . ?
C3 C2 C7 119.7(3) . . ?
C3 C2 C1 121.4(3) . . ?
C7 C2 C1 118.9(3) . . ?
C2 C3 C4 119.6(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.9(3) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 C8 116.9(3) . . ?
C6 C5 C8 122.7(3) . . ?
C7 C6 C5 118.2(3) . . ?
C7 C6 C9 119.4(3) . . ?
C5 C6 C9 122.4(3) . . ?
C2 C7 C6 121.5(3) . . ?
C2 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
O4 C8 O3 122.9(3) . . ?
O4 C8 C5 120.5(3) . . ?
O3 C8 C5 116.5(3) . . ?
C10 C9 C13 116.7(3) . . ?
C10 C9 C6 122.1(3) . . ?
C13 C9 C6 121.2(3) . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
N1W C11 C10 121.9(3) . . ?
N1W C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
N1W C12 C13 122.4(3) . . ?
N1W C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C12 C13 C9 119.9(3) . . ?
C12 C13 H13 120.1 . . ?
C9 C13 H13 120.1 . . ?
H1 O1W H2 122.8 . . ?

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 O1 C1 O2 -5.2(3) . . . . ?
Zn1 O1 C1 C2 171.6(3) . . . . ?
Zn1 O2 C1 O1 6.8(4) . . . . ?
Zn1 O2 C1 C2 -170.1(2) . . . . ?
O1 C1 C2 C3 -167.9(3) . . . . ?
O2 C1 C2 C3 9.1(5) . . . . ?
Zn1 C1 C2 C3 -14.8(9) . . . . ?
O1 C1 C2 C7 8.6(5) . . . . ?
O2 C1 C2 C7 -174.4(3) . . . . ?
Zn1 C1 C2 C7 161.7(6) . . . . ?
C7 C2 C3 C4 -1.4(5) . . . . ?
C1 C2 C3 C4 175.0(3) . . . . ?
C2 C3 C4 C5 -1.7(5) . . . . ?
C3 C4 C5 C6 4.0(5) . . . . ?
C3 C4 C5 C8 -169.9(3) . . . . ?
C4 C5 C6 C7 -3.1(5) . . . . ?
C8 C5 C6 C7 170.4(3) . . . . ?
C4 C5 C6 C9 175.0(3) . . . . ?
C8 C5 C6 C9 -11.5(5) . . . . ?
C3 C2 C7 C6 2.3(5) . . . . ?
C1 C2 C7 C6 -174.2(3) . . . . ?
C5 C6 C7 C2 0.0(5) . . . . ?
C9 C6 C7 C2 -178.2(3) . . . . ?
Zn1 O4 C8 O3 162.6(2) 5_556 . . . ?
Zn1 O4 C8 C5 -14.6(5) 5_556 . . . ?
Zn1 O3 C8 O4 -18.9(4) 8_556 . . . ?
Zn1 O3 C8 C5 158.4(2) 8_556 . . . ?
C4 C5 C8 O4 120.8(3) . . . . ?
C6 C5 C8 O4 -52.9(4) . . . . ?
C4 C5 C8 O3 -56.6(4) . . . . ?
C6 C5 C8 O3 129.7(3) . . . . ?
C7 C6 C9 C10 142.4(3) . . . . ?
C5 C6 C9 C10 -35.7(5) . . . . ?
C7 C6 C9 C13 -36.1(4) . . . . ?
C5 C6 C9 C13 145.9(3) . . . . ?
C13 C9 C10 C11 -0.5(5) . . . . ?
C6 C9 C10 C11 -179.0(3) . . . . ?
C12 N1W C11 C10 -0.4(5) . . . . ?
Zn1 N1W C11 C10 173.6(2) 3 . . . ?
C9 C10 C11 N1W 1.0(5) . . . . ?
C11 N1W C12 C13 -0.7(5) . . . . ?
Zn1 N1W C12 C13 -174.8(3) 3 . . . ?
N1W C12 C13 C9 1.1(5) . . . . ?
C10 C9 C13 C12 -0.5(5) . . . . ?
C6 C9 C13 C12 178.1(3) . . . . ?

_refine_diff_density_max         0.472
_refine_diff_density_min         -0.871
_refine_diff_density_rms         0.108

