# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1557102'
_audit_update_record             
;
2018-02-08 deposited with the CCDC.
2018-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ' C22 H18 N2 O5 Zn, H2 O'
_chemical_formula_sum            'C22 H20 N2 O6 Zn'
_chemical_formula_weight         473.77

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.6150(15)
_cell_length_b                   26.006(4)
_cell_length_c                   10.0175(17)
_cell_angle_alpha                90
_cell_angle_beta                 113.667(2)
_cell_angle_gamma                90
_cell_volume                     2055.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1257
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      22.15

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.24
_exptl_absorpt_coefficient_mu    1.238
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11538
_diffrn_reflns_av_unetI/netI     0.0835
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.566
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             3615
_reflns_number_gt                2215
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0466P)²] 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         3602
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_restrained_S_all      0.978
_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 0.74471(6) 0.11807(2) 1.05554(5) 0.02842(17) Uani 1 1 d . . . . .
O1 O 0.6060(3) 0.07107(11) 0.8972(3) 0.0409(8) Uani 1 1 d . . . . .
O2 O 0.4961(4) 0.14488(11) 0.7928(3) 0.0441(9) Uani 1 1 d . . . . .
O4 O -0.0256(4) 0.14215(12) 0.3260(3) 0.0432(8) Uani 1 1 d . . . . .
O3 O -0.0993(3) 0.06973(11) 0.2008(3) 0.0384(8) Uani 1 1 d . . . . .
O5 O 0.3133(4) -0.06344(11) 0.5321(3) 0.0532(10) Uani 1 1 d . . . . .
N2 N 1.5899(4) 0.34574(14) 0.6339(4) 0.0316(9) Uani 1 1 d . . . . .
N1 N 0.8968(4) 0.15824(13) 0.9801(4) 0.0310(9) Uani 1 1 d . . . . .
C12 C 1.4896(5) 0.37452(18) 0.6754(5) 0.0370(11) Uani 1 1 d . . . . .
H12 H 1.4924 0.4100 0.6658 0.044 Uiso 1 1 calc R U . . .
C11 C 1.3812(5) 0.35359(17) 0.7323(5) 0.0375(11) Uani 1 1 d . . . . .
H11 H 1.3133 0.3752 0.7600 0.045 Uiso 1 1 calc R U . . .
C10 C 1.3727(5) 0.30083(17) 0.7483(4) 0.0309(10) Uani 1 1 d . . . . .
C9 C 1.4814(5) 0.27132(17) 0.7062(5) 0.0394(12) Uani 1 1 d . . . . .
H9 H 1.4822 0.2357 0.7149 0.047 Uiso 1 1 calc R U . . .
C8 C 1.5870(6) 0.29476(18) 0.6521(5) 0.0417(12) Uani 1 1 d . . . . .
H8 H 1.6597 0.2743 0.6270 0.050 Uiso 1 1 calc R U . . .
C7 C 1.2552(5) 0.27831(18) 0.8032(5) 0.0393(12) Uani 1 1 d . . . . .
H7 H 1.1908 0.3009 0.8319 0.047 Uiso 1 1 calc R U . . .
C6 C 1.2316(5) 0.22866(18) 0.8160(5) 0.0383(12) Uani 1 1 d . . . . .
H6 H 1.2963 0.2061 0.7874 0.046 Uiso 1 1 calc R U . . .
C5 C 1.0072(5) 0.13102(16) 0.9458(5) 0.0345(11) Uani 1 1 d . . . . .
H5 H 1.0114 0.0956 0.9597 0.041 Uiso 1 1 calc R U . . .
C4 C 1.1144(5) 0.15270(18) 0.8910(5) 0.0366(12) Uani 1 1 d . . . . .
H4 H 1.1878 0.1320 0.8674 0.044 Uiso 1 1 calc R U . . .
C3 C 1.1135(5) 0.20560(18) 0.8708(4) 0.0324(11) Uani 1 1 d . . . . .
C2 C 0.9977(5) 0.23413(17) 0.9062(5) 0.0378(12) Uani 1 1 d . . . . .
H2 H 0.9920 0.2697 0.8952 0.045 Uiso 1 1 calc R U . . .
C1 C 0.8929(5) 0.20907(17) 0.9573(5) 0.0384(12) Uani 1 1 d . . . . .
H1 H 0.8143 0.2285 0.9775 0.046 Uiso 1 1 calc R U . . .
C13 C 0.3788(5) 0.06796(16) 0.6617(5) 0.0308(10) Uani 1 1 d . . . . .
C14 C 0.2465(5) 0.09403(16) 0.5519(5) 0.0323(10) Uani 1 1 d . . . . .
H14 H 0.2337 0.1293 0.5589 0.039 Uiso 1 1 calc R U . . .
C15 C 0.1342(5) 0.06696(16) 0.4321(4) 0.0297(10) Uani 1 1 d . . . . .
C16 C 0.1549(5) 0.01434(17) 0.4221(5) 0.0373(12) Uani 1 1 d . . . . .
H16 H 0.0810 -0.0036 0.3413 0.045 Uiso 1 1 calc R U . . .
C17 C 0.2838(5) -0.01165(17) 0.5305(5) 0.0382(12) Uani 1 1 d . . . . .
C18 C 0.3964(5) 0.01554(17) 0.6505(5) 0.0364(12) Uani 1 1 d . . . . .
H18 H 0.4841 -0.0018 0.7236 0.044 Uiso 1 1 calc R U . . .
C19 C 0.4999(5) 0.09751(18) 0.7907(5) 0.0316(11) Uani 1 1 d . . . . .
C20 C -0.0056(5) 0.09574(18) 0.3143(5) 0.0312(11) Uani 1 1 d . . . . .
C21 C 0.2105(6) -0.09268(17) 0.4075(5) 0.0435(13) Uani 1 1 d . . . . .
H21A H 0.2243 -0.0805 0.3214 0.052 Uiso 1 1 calc R U . . .
H21B H 0.0919 -0.0898 0.3911 0.052 Uiso 1 1 calc R U . . .
C22 C 0.2691(6) -0.14793(18) 0.4396(5) 0.0572(15) Uani 1 1 d . . . . .
H22A H 0.2040 -0.1691 0.3578 0.086 Uiso 1 1 calc R U . . .
H22B H 0.2536 -0.1595 0.5244 0.086 Uiso 1 1 calc R U . . .
H22C H 0.3869 -0.1501 0.4569 0.086 Uiso 1 1 calc R U . . .
O1W O 0.2157(8) 0.0258(2) 0.9726(8) 0.278(5) Uani 1 1 d . . . . .
H1WA H 0.1486 0.0082 0.9012 0.417 Uiso 1 1 d R U . . .
H1WB H 0.3102 0.0103 1.0115 0.417 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 O1 1.979(3) . ?
Zn1 O3 1.984(3) 1_656 ?
Zn1 N2 2.030(3) 4_466 ?
Zn1 N1 2.043(3) . ?
O1 C19 1.290(5) . ?
O2 C19 1.233(5) . ?
O4 C20 1.232(5) . ?
O3 C20 1.290(5) . ?
O3 Zn1 1.984(3) 1_454 ?
O5 C17 1.369(5) . ?
O5 C21 1.425(5) . ?
N2 C12 1.329(5) . ?
N2 C8 1.340(5) . ?
N2 Zn1 2.030(3) 4_665 ?
N1 C5 1.336(5) . ?
N1 C1 1.340(5) . ?
C12 C11 1.386(5) . ?
C12 H12 0.9300 . ?
C11 C10 1.387(6) . ?
C11 H11 0.9300 . ?
C10 C9 1.401(6) . ?
C10 C7 1.454(6) . ?
C9 C8 1.374(6) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C7 C6 1.321(6) . ?
C7 H7 0.9300 . ?
C6 C3 1.464(6) . ?
C6 H6 0.9300 . ?
C5 C4 1.371(5) . ?
C5 H5 0.9300 . ?
C4 C3 1.390(6) . ?
C4 H4 0.9300 . ?
C3 C2 1.398(6) . ?
C2 C1 1.369(5) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?
C13 C18 1.381(6) . ?
C13 C14 1.401(5) . ?
C13 C19 1.505(5) . ?
C14 C15 1.393(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.389(6) . ?
C15 C20 1.504(5) . ?
C16 C17 1.379(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.397(6) . ?
C18 H18 0.9300 . ?
C21 C22 1.514(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
O1W H1WA 0.8501 . ?
O1W H1WB 0.8499 . ?

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 O3 102.12(12) . 1_656 ?
O1 Zn1 N2 108.51(13) . 4_466 ?
O3 Zn1 N2 111.52(13) 1_656 4_466 ?
O1 Zn1 N1 106.84(13) . . ?
O3 Zn1 N1 104.43(13) 1_656 . ?
N2 Zn1 N1 121.63(14) 4_466 . ?
C19 O1 Zn1 109.5(3) . . ?
C20 O3 Zn1 108.3(3) . 1_454 ?
C17 O5 C21 117.9(3) . . ?
C12 N2 C8 117.7(4) . . ?
C12 N2 Zn1 118.0(3) . 4_665 ?
C8 N2 Zn1 124.2(3) . 4_665 ?
C5 N1 C1 116.8(4) . . ?
C5 N1 Zn1 116.9(3) . . ?
C1 N1 Zn1 126.3(3) . . ?
N2 C12 C11 122.5(4) . . ?
N2 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
C12 C11 C10 120.8(4) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C10 C9 115.7(4) . . ?
C11 C10 C7 121.3(4) . . ?
C9 C10 C7 123.0(4) . . ?
C8 C9 C10 120.3(4) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
N2 C8 C9 123.0(4) . . ?
N2 C8 H8 118.5 . . ?
C9 C8 H8 118.5 . . ?
C6 C7 C10 126.0(4) . . ?
C6 C7 H7 117.0 . . ?
C10 C7 H7 117.0 . . ?
C7 C6 C3 126.5(4) . . ?
C7 C6 H6 116.8 . . ?
C3 C6 H6 116.8 . . ?
N1 C5 C4 123.3(4) . . ?
N1 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
C5 C4 C3 120.0(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C3 C2 116.8(4) . . ?
C4 C3 C6 119.7(4) . . ?
C2 C3 C6 123.5(4) . . ?
C1 C2 C3 119.2(4) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
N1 C1 C2 123.9(4) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C18 C13 C14 119.7(4) . . ?
C18 C13 C19 120.8(4) . . ?
C14 C13 C19 119.5(4) . . ?
C15 C14 C13 119.8(4) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 119.7(4) . . ?
C16 C15 C20 121.3(4) . . ?
C14 C15 C20 119.0(4) . . ?
C17 C16 C15 120.8(4) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
O5 C17 C16 125.3(4) . . ?
O5 C17 C18 115.3(4) . . ?
C16 C17 C18 119.4(4) . . ?
C13 C18 C17 120.6(4) . . ?
C13 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
O2 C19 O1 122.2(4) . . ?
O2 C19 C13 120.7(4) . . ?
O1 C19 C13 117.0(4) . . ?
O4 C20 O3 122.4(4) . . ?
O4 C20 C15 120.8(4) . . ?
O3 C20 C15 116.8(4) . . ?
O5 C21 C22 106.5(3) . . ?
O5 C21 H21A 110.4 . . ?
C22 C21 H21A 110.4 . . ?
O5 C21 H21B 110.4 . . ?
C22 C21 H21B 110.4 . . ?
H21A C21 H21B 108.6 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
H1WA O1W H1WB 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N2 C12 C11 -1.7(6) . . . . ?
Zn1 N2 C12 C11 -179.1(3) 4_665 . . . ?
N2 C12 C11 C10 -0.1(7) . . . . ?
C12 C11 C10 C9 1.1(6) . . . . ?
C12 C11 C10 C7 -177.9(4) . . . . ?
C11 C10 C9 C8 -0.4(6) . . . . ?
C7 C10 C9 C8 178.5(4) . . . . ?
C12 N2 C8 C9 2.4(6) . . . . ?
Zn1 N2 C8 C9 179.6(3) 4_665 . . . ?
C10 C9 C8 N2 -1.4(7) . . . . ?
C11 C10 C7 C6 176.6(5) . . . . ?
C9 C10 C7 C6 -2.3(7) . . . . ?
C10 C7 C6 C3 -179.9(4) . . . . ?
C1 N1 C5 C4 0.6(6) . . . . ?
Zn1 N1 C5 C4 178.6(3) . . . . ?
N1 C5 C4 C3 1.0(7) . . . . ?
C5 C4 C3 C2 -1.1(6) . . . . ?
C5 C4 C3 C6 178.3(4) . . . . ?
C7 C6 C3 C4 -173.8(5) . . . . ?
C7 C6 C3 C2 5.6(7) . . . . ?
C4 C3 C2 C1 -0.2(6) . . . . ?
C6 C3 C2 C1 -179.7(4) . . . . ?
C5 N1 C1 C2 -2.1(6) . . . . ?
Zn1 N1 C1 C2 -179.9(3) . . . . ?
C3 C2 C1 N1 2.0(7) . . . . ?
C18 C13 C14 C15 -0.2(6) . . . . ?
C19 C13 C14 C15 179.8(4) . . . . ?
C13 C14 C15 C16 -0.4(6) . . . . ?
C13 C14 C15 C20 -179.2(4) . . . . ?
C14 C15 C16 C17 1.0(7) . . . . ?
C20 C15 C16 C17 179.8(4) . . . . ?
C21 O5 C17 C16 4.6(7) . . . . ?
C21 O5 C17 C18 -175.4(4) . . . . ?
C15 C16 C17 O5 178.9(4) . . . . ?
C15 C16 C17 C18 -1.1(7) . . . . ?
C14 C13 C18 C17 0.1(6) . . . . ?
C19 C13 C18 C17 -179.9(4) . . . . ?
O5 C17 C18 C13 -179.5(4) . . . . ?
C16 C17 C18 C13 0.5(7) . . . . ?
Zn1 O1 C19 O2 2.0(5) . . . . ?
Zn1 O1 C19 C13 -177.9(3) . . . . ?
C18 C13 C19 O2 171.7(4) . . . . ?
C14 C13 C19 O2 -8.3(6) . . . . ?
C18 C13 C19 O1 -8.4(6) . . . . ?
C14 C13 C19 O1 171.6(4) . . . . ?
Zn1 O3 C20 O4 4.5(5) 1_454 . . . ?
Zn1 O3 C20 C15 -174.0(3) 1_454 . . . ?
C16 C15 C20 O4 178.1(4) . . . . ?
C14 C15 C20 O4 -3.1(6) . . . . ?
C16 C15 C20 O3 -3.4(6) . . . . ?
C14 C15 C20 O3 175.4(4) . . . . ?
C17 O5 C21 C22 -179.4(4) . . . . ?

_refine_diff_density_max         0.745
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.078

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1557109'
_audit_update_record             
;
2018-02-08 deposited with the CCDC.
2018-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H22 N2 O5 Zn'
_chemical_formula_sum            'C23 H22 N2 O5 Zn'
_chemical_formula_weight         471.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2840 1.4300 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_H-M_alt        'C m c a'
_space_group_name_Hall           '-C 2bc 2'

_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+1/2'
'x, -y, -z'
'-x, y+1/2, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1, -z+1/2'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x, y, z'
'x, -y-1/2, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'-x+1/2, y+1/2, z'
'x+1/2, -y, z-1/2'

_cell_length_a                   18.696(2)
_cell_length_b                   14.2482(17)
_cell_length_c                   16.1635(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4305.7(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2283
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      20.83

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_F_000             1952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    1.178
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12107
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.179
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2079
_reflns_number_gt                1439
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0894P)²+24.4204P] 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         2064
_refine_ls_number_parameters     208
_refine_ls_number_restraints     87
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0706
_refine_ls_wR_factor_ref         0.2037
_refine_ls_wR_factor_gt          0.1929
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.113
_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 0.2500 0.22581(5) 0.2500 0.0503(2) Uani 1 2 d S TU P A .
O1 O 0.3621(2) 0.2002(3) 0.2175(3) 0.0739(11) Uani 1 1 d . . . . .
O2 O 0.31223(18) 0.1223(3) 0.3176(2) 0.0702(9) Uani 1 1 d . U . . .
N1 N 0.2596(2) 0.3265(3) 0.3446(2) 0.0539(10) Uani 1 1 d . . . . .
C1 C 0.2378(6) 0.3121(8) 0.4171(7) 0.054(3) Uani 0.5 1 d . . P A 1
H1 H 0.2177 0.2537 0.4280 0.065 Uiso 0.5 1 calc R U P A 1
C2 C 0.2411(7) 0.3754(8) 0.4822(7) 0.064(3) Uani 0.5 1 d . . P A 1
H2 H 0.2266 0.3577 0.5350 0.077 Uiso 0.5 1 calc R U P A 1
C3 C 0.2657(3) 0.4630(3) 0.4682(3) 0.0525(12) Uani 1 1 d . . . . .
C4' C 0.3154(7) 0.4566(10) 0.4076(8) 0.085(4) Uani 0.5 1 d . . P A 2
H4' H 0.3528 0.4996 0.4049 0.102 Uiso 0.5 1 calc R U P A 2
C5' C 0.3101(7) 0.3872(10) 0.3513(8) 0.077(4) Uani 0.5 1 d . . P A 2
H5' H 0.3470 0.3828 0.3130 0.092 Uiso 0.5 1 calc R U P A 2
C7 C 0.4358(2) 0.0958(3) 0.2940(3) 0.0503(12) Uani 1 1 d . . . . .
C8 C 0.5000 0.1349(4) 0.2684(4) 0.0450(15) Uani 1 2 d S T P . .
H8 H 0.5000 0.1873 0.2340 0.054 Uiso 1 2 calc R U P . .
C9 C 0.4352(3) 0.0166(3) 0.3443(3) 0.0602(13) Uani 1 1 d . . . . .
H9 H 0.3924 -0.0092 0.3629 0.072 Uiso 1 1 calc R U . . .
C10 C 0.5000 -0.0225(4) 0.3658(4) 0.065(2) Uani 1 2 d DS T P . .
C6 C 0.3658(3) 0.1414(4) 0.2749(3) 0.0563(12) Uani 1 1 d . . . . .
O3 O 0.4850(4) -0.1050(5) 0.4177(5) 0.110(3) Uani 0.5 1 d D U P B -1
C11 C 0.5501(5) -0.1611(8) 0.4409(10) 0.129(3) Uani 0.5 1 d D U P B -1
H11A H 0.5724 -0.1354 0.4901 0.155 Uiso 0.5 1 calc R U P B -1
H11B H 0.5847 -0.1607 0.3962 0.155 Uiso 0.5 1 calc R U P B -1
C15 C 0.5128(13) -0.3822(11) 0.6300(9) 0.175(5) Uani 0.5 1 d D U P B -1
H15A H 0.5499 -0.3357 0.6296 0.263 Uiso 0.5 1 calc R U P B -1
H15B H 0.5338 -0.4436 0.6273 0.263 Uiso 0.5 1 calc R U P B -1
H15C H 0.4853 -0.3766 0.6799 0.263 Uiso 0.5 1 calc R U P B -1
C14 C 0.4640(10) -0.3677(10) 0.5554(9) 0.174(4) Uani 0.5 1 d D U P B -1
H14A H 0.4150 -0.3821 0.5703 0.209 Uiso 0.5 1 calc R U P B -1
H14B H 0.4782 -0.4095 0.5109 0.209 Uiso 0.5 1 calc R U P B -1
C4 C 0.2909(6) 0.4820(7) 0.3881(6) 0.053(3) Uani 0.5 1 d . . P A 1
H4 H 0.3086 0.5415 0.3759 0.064 Uiso 0.5 1 calc R U P A 1
C5 C 0.2899(6) 0.4144(6) 0.3276(6) 0.051(3) Uani 0.5 1 d . . P A 1
H5 H 0.3093 0.4268 0.2757 0.061 Uiso 0.5 1 calc R U P A 1
C1' C 0.2079(6) 0.3309(8) 0.4059(6) 0.053(3) Uani 0.5 1 d . . P A 2
H1' H 0.1708 0.2874 0.4054 0.063 Uiso 0.5 1 calc R U P A 2
C2' C 0.2097(7) 0.3979(8) 0.4676(7) 0.064(3) Uani 0.5 1 d . . P A 2
H2' H 0.1743 0.3997 0.5080 0.076 Uiso 0.5 1 calc R U P A 2
C12 C 0.5226(8) -0.2631(7) 0.4574(9) 0.145(3) Uani 0.5 1 d D U P B -1
H12A H 0.5007 -0.2880 0.4076 0.174 Uiso 0.5 1 calc R U P B -1
H12B H 0.5627 -0.3032 0.4719 0.174 Uiso 0.5 1 calc R U P B -1
C13 C 0.4696(8) -0.2629(9) 0.5258(9) 0.165(3) Uani 0.5 1 d D U P B -1
H13A H 0.4236 -0.2405 0.5063 0.198 Uiso 0.5 1 calc R U P B -1
H13B H 0.4856 -0.2228 0.5706 0.198 Uiso 0.5 1 calc R U P B -1


_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 N1 2.104(4) . ?
Zn1 N1 2.104(4) 8_545 ?
Zn1 O2 2.173(4) . ?
Zn1 O2 2.173(4) 8_545 ?
Zn1 O1 2.192(4) . ?
Zn1 O1 2.192(4) 8_545 ?
Zn1 C6 2.509(5) . ?
Zn1 C6 2.509(5) 8_545 ?
O1 C6 1.253(6) . ?
O2 C6 1.246(6) . ?
N1 C1 1.257(11) . ?
N1 C5' 1.284(14) . ?
N1 C1' 1.386(11) . ?
N1 C5 1.402(10) . ?
C1 C2 1.388(16) . ?
C1 H1 0.9300 . ?
C2 C3 1.349(12) . ?
C2 H2 0.9300 . ?
C3 C4' 1.352(14) . ?
C3 C4 1.403(11) . ?
C3 C2' 1.400(13) . ?
C3 C3 1.474(9) 3_566 ?
C4' C5' 1.348(18) . ?
C4' H4' 0.9300 . ?
C5' H5' 0.9300 . ?
C7 C8 1.386(5) . ?
C7 C9 1.392(7) . ?
C7 C6 1.494(7) . ?
C8 C7 1.386(5) 11_655 ?
C8 H8 0.9300 . ?
C9 C10 1.378(6) . ?
C9 H9 0.9300 . ?
C10 C9 1.378(6) 11_655 ?
C10 O3 1.471(7) . ?
O3 C11 1.503(8) . ?
C11 C12 1.564(13) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C15 C14 1.526(16) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14 C13 1.572(14) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C4 C5 1.373(14) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C1' C2' 1.381(15) . ?
C1' H1' 0.9300 . ?
C2' H2' 0.9300 . ?
C12 C13 1.485(15) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 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
N1 Zn1 N1 94.1(2) . 8_545 ?
N1 Zn1 O2 92.97(15) . . ?
N1 Zn1 O2 150.89(15) 8_545 . ?
N1 Zn1 O2 150.89(15) . 8_545 ?
N1 Zn1 O2 92.97(15) 8_545 8_545 ?
O2 Zn1 O2 94.5(2) . 8_545 ?
N1 Zn1 O1 101.89(16) . . ?
N1 Zn1 O1 91.19(15) 8_545 . ?
O2 Zn1 O1 59.71(14) . . ?
O2 Zn1 O1 106.17(15) 8_545 . ?
N1 Zn1 O1 91.19(15) . 8_545 ?
N1 Zn1 O1 101.89(15) 8_545 8_545 ?
O2 Zn1 O1 106.17(15) . 8_545 ?
O2 Zn1 O1 59.71(14) 8_545 8_545 ?
O1 Zn1 O1 160.9(2) . 8_545 ?
N1 Zn1 C6 97.83(15) . . ?
N1 Zn1 C6 121.14(16) 8_545 . ?
O2 Zn1 C6 29.77(15) . . ?
O2 Zn1 C6 102.55(15) 8_545 . ?
O1 Zn1 C6 29.95(15) . . ?
O1 Zn1 C6 134.99(17) 8_545 . ?
N1 Zn1 C6 121.14(16) . 8_545 ?
N1 Zn1 C6 97.82(15) 8_545 8_545 ?
O2 Zn1 C6 102.55(15) . 8_545 ?
O2 Zn1 C6 29.77(15) 8_545 8_545 ?
O1 Zn1 C6 134.99(17) . 8_545 ?
O1 Zn1 C6 29.95(15) 8_545 8_545 ?
C6 Zn1 C6 122.7(2) . 8_545 ?
C6 O1 Zn1 89.2(3) . . ?
C6 O2 Zn1 90.2(3) . . ?
C5' N1 C1' 115.0(7) . . ?
C1 N1 C5 117.4(7) . . ?
C1 N1 Zn1 122.5(6) . . ?
C5' N1 Zn1 125.7(6) . . ?
C1' N1 Zn1 119.4(5) . . ?
C5 N1 Zn1 120.1(5) . . ?
N1 C1 C2 125.9(10) . . ?
N1 C1 H1 117.1 . . ?
C2 C1 H1 117.1 . . ?
C3 C2 C1 119.2(10) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 116.7(7) . . ?
C4' C3 C2' 117.7(8) . . ?
C4' C3 C3 123.6(6) . 3_566 ?
C2 C3 C3 123.0(7) . 3_566 ?
C4 C3 C3 120.3(6) . 3_566 ?
C2' C3 C3 118.6(6) . 3_566 ?
C3 C4' C5' 119.1(11) . . ?
C3 C4' H4' 120.4 . . ?
C5' C4' H4' 120.4 . . ?
N1 C5' C4' 127.3(11) . . ?
N1 C5' H5' 116.4 . . ?
C4' C5' H5' 116.4 . . ?
C8 C7 C9 120.6(4) . . ?
C8 C7 C6 121.5(4) . . ?
C9 C7 C6 117.7(4) . . ?
C7 C8 C7 119.9(6) . 11_655 ?
C7 C8 H8 120.0 . . ?
C7 C8 H8 120.0 11_655 . ?
C10 C9 C7 117.8(5) . . ?
C10 C9 H9 121.1 . . ?
C7 C9 H9 121.1 . . ?
C9 C10 C9 123.2(6) . 11_655 ?
C9 C10 O3 107.4(4) . . ?
C9 C10 O3 129.3(5) 11_655 . ?
O2 C6 O1 120.9(5) . . ?
O2 C6 C7 119.7(5) . . ?
O1 C6 C7 119.5(4) . . ?
O2 C6 Zn1 60.0(3) . . ?
O1 C6 Zn1 60.9(3) . . ?
C7 C6 Zn1 176.3(4) . . ?
C10 O3 C11 114.4(7) . . ?
O3 C11 C12 105.8(8) . . ?
O3 C11 H11A 110.6 . . ?
C12 C11 H11A 110.6 . . ?
O3 C11 H11B 110.6 . . ?
C12 C11 H11B 110.6 . . ?
H11A C11 H11B 108.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C15 C14 C13 109.2(12) . . ?
C15 C14 H14A 109.8 . . ?
C13 C14 H14A 109.8 . . ?
C15 C14 H14B 109.8 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.3 . . ?
C5 C4 C3 121.1(8) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 N1 119.5(8) . . ?
C4 C5 H5 120.2 . . ?
N1 C5 H5 120.2 . . ?
N1 C1' C2' 122.1(9) . . ?
N1 C1' H1' 119.0 . . ?
C2' C1' H1' 119.0 . . ?
C1' C2' C3 118.7(10) . . ?
C1' C2' H2' 120.6 . . ?
C3 C2' H2' 120.6 . . ?
C13 C12 C11 110.1(10) . . ?
C13 C12 H12A 109.6 . . ?
C11 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.2 . . ?
C12 C13 C14 105.6(11) . . ?
C12 C13 H13A 110.6 . . ?
C14 C13 H13A 110.6 . . ?
C12 C13 H13B 110.6 . . ?
C14 C13 H13B 110.6 . . ?
H13A C13 H13B 108.7 . . ?

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
C5'_b N1 C1_a C2_a 27.4(15) . . . . ?
C1' N1 C1 C2 -86.6(19) . . . . ?
C5 N1 C1 C2 -0.1(15) . . . . ?
Zn1 N1 C1 C2 -178.8(9) . . . . ?
N1 C1 C2 C3 4.2(18) . . . . ?
C1 C2 C3 C4' -32.2(14) . . . . ?
C1 C2 C3 C4 -4.0(15) . . . . ?
C1 C2 C3 C2' 84.0(17) . . . . ?
C1 C2 C3 C3 175.0(8) . . . 3_566 ?
C2 C3 C4' C5' 28.6(16) . . . . ?
C4 C3 C4' C5' -86.5(19) . . . . ?
C2' C3 C4' C5' -1.8(17) . . . . ?
C3 C3 C4' C5' -178.8(10) 3_566 . . . ?
C1 N1 C5' C4' -32.2(17) . . . . ?
C1' N1 C5' C4' -4.2(18) . . . . ?
C5 N1 C5' C4' 87(2) . . . . ?
Zn1 N1 C5' C4' 175.1(11) . . . . ?
C3 C4' C5' N1 4(2) . . . . ?
C9 C7 C8 C7 -1.0(9) . . . 11_655 ?
C6 C7 C8 C7 173.7(4) . . . 11_655 ?
C8 C7 C9 C10 -1.6(8) . . . . ?
C6 C7 C9 C10 -176.4(5) . . . . ?
C7 C9 C10 C9 4.3(11) . . . 11_655 ?
C7 C9 C10 O3 -179.4(5) . . . . ?
Zn1 O2 C6 O1 -2.5(5) . . . . ?
Zn1 O2 C6 C7 175.7(4) . . . . ?
Zn1 O1 C6 O2 2.5(5) . . . . ?
Zn1 O1 C6 C7 -175.7(4) . . . . ?
C8 C7 C6 O2 -158.7(5) . . . . ?
C9 C7 C6 O2 16.1(7) . . . . ?
C8 C7 C6 O1 19.6(7) . . . . ?
C9 C7 C6 O1 -165.6(5) . . . . ?
C9 C10 O3 C11 175.0(9) . . . . ?
C9 C10 O3 C11 -8.9(13) 11_655 . . . ?
C10 O3 C11 C12 -154.3(9) . . . . ?
C4' C3 C4 C5 76.0(17) . . . . ?
C2 C3 C4 C5 0.3(14) . . . . ?
C2' C3 C4 C5 -32.2(13) . . . . ?
C3 C3 C4 C5 -178.7(8) 3_566 . . . ?
C3 C4 C5 N1 3.6(15) . . . . ?
C1 N1 C5 C4 -3.7(13) . . . . ?
C5' N1 C5 C4 -74.8(17) . . . . ?
C1' N1 C5 C4 26.5(12) . . . . ?
Zn1 N1 C5 C4 175.0(8) . . . . ?
C1 N1 C1' C2' 77.9(17) . . . . ?
C5' N1 C1' C2' 2.1(14) . . . . ?
C5 N1 C1' C2' -28.5(13) . . . . ?
Zn1 N1 C1' C2' -177.3(8) . . . . ?
N1 C1' C2' C3 -0.2(16) . . . . ?
C4' C3 C2' C1' 0.1(15) . . . . ?
C2 C3 C2' C1' -75.6(16) . . . . ?
C4 C3 C2' C1' 30.1(13) . . . . ?
C3 C3 C2' C1' 177.3(8) 3_566 . . . ?
O3 C11 C12 C13 -60.1(15) . . . . ?
C11 C12 C13 C14 -162.9(12) . . . . ?
C15 C14 C13 C12 96.3(16) . . . . ?

_refine_diff_density_max         0.599
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.087

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1557104'
_audit_update_record             
;
2018-02-08 deposited with the CCDC.
2018-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H22 N2 O5 Zn'
_chemical_formula_sum            'C24 H22 N2 O5 Zn'
_chemical_formula_weight         483.80

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                   8.482(7)
_cell_length_b                   10.245(8)
_cell_length_c                   15.967(12)
_cell_angle_alpha                99.022(10)
_cell_angle_beta                 93.005(10)
_cell_angle_gamma                114.363(9)
_cell_volume                     1237.7(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2045
_cell_measurement_theta_min      4.26
_cell_measurement_theta_max      25.56

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             500
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    1.026
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9713
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.605
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.959
_reflns_number_total             4356
_reflns_number_gt                3320
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0431P)²] 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         4285
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.0905
_refine_ls_wR_factor_gt          0.0851
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.974
_refine_ls_shift/su_max          0.002
_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 1.07396(4) 0.34006(3) 0.21863(2) 0.02976(12) Uani 1 1 d . . . . .
O2 O 0.8203(3) 0.0638(2) 0.17458(13) 0.0443(5) Uani 1 1 d . . . . .
O4 O 0.2486(3) -0.4844(2) 0.29778(12) 0.0410(5) Uani 1 1 d . . . . .
O1 O 0.9490(2) 0.2144(2) 0.29801(12) 0.0389(5) Uani 1 1 d . . . . .
O3 O 0.3030(3) -0.4088(2) 0.17583(13) 0.0443(6) Uani 1 1 d . . . . .
O5 O 0.6663(3) -0.0805(2) 0.52175(13) 0.0667(8) Uani 1 1 d . . . . .
N1 N 1.2092(3) 0.2423(2) 0.15346(15) 0.0318(6) Uani 1 1 d . . . . .
N2 N 0.9008(3) 0.3947(2) 0.15700(15) 0.0327(6) Uani 1 1 d . . . . .
C22 C 0.7970(4) 0.0379(3) 0.66325(19) 0.0477(8) Uani 1 1 d . . . . .
H22A H 0.8213 -0.0441 0.6716 0.057 Uiso 1 1 calc R U . . .
H22B H 0.6808 0.0182 0.6777 0.057 Uiso 1 1 calc R U . . .
C19 C 0.8367(4) 0.0923(3) 0.25372(19) 0.0332(7) Uani 1 1 d . . . . .
C23 C 0.9289(4) 0.1759(3) 0.72282(19) 0.0490(9) Uani 1 1 d . . . . .
H23A H 1.0452 0.1934 0.7094 0.059 Uiso 1 1 calc R U . . .
H23B H 0.9070 0.2582 0.7126 0.059 Uiso 1 1 calc R U . . .
C24 C 0.9223(5) 0.1678(4) 0.8162(2) 0.0675(11) Uani 1 1 d . . . . .
H24A H 0.9518 0.0908 0.8277 0.101 Uiso 1 1 calc R U . . .
H24B H 0.8068 0.1483 0.8298 0.101 Uiso 1 1 calc R U . . .
H24C H 1.0042 0.2591 0.8506 0.101 Uiso 1 1 calc R U . . .
C21 C 0.8020(4) 0.0509(3) 0.57164(19) 0.0498(9) Uani 1 1 d . . . . .
H21A H 0.7832 0.1352 0.5627 0.060 Uiso 1 1 calc R U . . .
H21B H 0.9147 0.0628 0.5549 0.060 Uiso 1 1 calc R U . . .
C20 C 0.3343(4) -0.3902(3) 0.25387(19) 0.0329(7) Uani 1 1 d . . . . .
C5 C 1.3373(4) 0.2297(3) 0.19933(19) 0.0358(7) Uani 1 1 d . . . . .
H5 H 1.3632 0.2704 0.2574 0.043 Uiso 1 1 calc R U . . .
C14 C 0.5873(3) -0.1480(3) 0.25813(18) 0.0325(7) Uani 1 1 d . . . . .
H14 H 0.5670 -0.1657 0.1987 0.039 Uiso 1 1 calc R U . . .
C9 C 0.6613(4) 0.4763(3) 0.07904(19) 0.0342(7) Uani 1 1 d . . . . .
C3 C 1.4003(4) 0.0995(3) 0.07731(19) 0.0341(7) Uani 1 1 d . . . . .
C7 C 0.8151(4) 0.4579(3) 0.20312(19) 0.0373(7) Uani 1 1 d . . . . .
H7 H 0.8357 0.4740 0.2624 0.045 Uiso 1 1 calc R U . . .
C12 C 0.5309(4) 0.5162(3) 0.04090(19) 0.0396(8) Uani 1 1 d . . . . .
H12 H 0.4875 0.5693 0.0778 0.047 Uiso 1 1 calc R U . . .
C2 C 1.2674(4) 0.1125(3) 0.02941(19) 0.0404(8) Uani 1 1 d . . . . .
H2 H 1.2408 0.0746 -0.0290 0.049 Uiso 1 1 calc R U . . .
C6 C 1.5044(4) 0.0267(3) 0.04039(18) 0.0389(7) Uani 1 1 d . . . . .
H6 H 1.5847 0.0175 0.0782 0.047 Uiso 1 1 calc R U . . .
C15 C 0.4819(4) -0.2510(3) 0.30200(18) 0.0329(7) Uani 1 1 d . . . . .
C16 C 0.5136(4) -0.2236(3) 0.39053(19) 0.0431(8) Uani 1 1 d . . . . .
H16 H 0.4441 -0.2921 0.4206 0.052 Uiso 1 1 calc R U . . .
C8 C 0.6977(4) 0.5003(3) 0.16682(19) 0.0385(7) Uani 1 1 d . . . . .
H8 H 0.6425 0.5453 0.2016 0.046 Uiso 1 1 calc R U . . .
C10 C 0.7520(4) 0.4122(4) 0.03094(19) 0.0423(8) Uani 1 1 d . . . . .
H10 H 0.7343 0.3953 -0.0285 0.051 Uiso 1 1 calc R U . . .
C4 C 1.4325(4) 0.1587(3) 0.16367(19) 0.0378(7) Uani 1 1 d . . . . .
H4 H 1.5188 0.1508 0.1981 0.045 Uiso 1 1 calc R U . . .
C13 C 0.7227(4) -0.0190(3) 0.30166(18) 0.0309(7) Uani 1 1 d . . . . .
C11 C 0.8675(4) 0.3743(4) 0.0722(2) 0.0437(8) Uani 1 1 d . . . . .
H11 H 0.9268 0.3315 0.0389 0.052 Uiso 1 1 calc R U . . .
C1 C 1.1759(4) 0.1825(3) 0.0700(2) 0.0411(8) Uani 1 1 d . . . . .
H1 H 1.0858 0.1886 0.0375 0.049 Uiso 1 1 calc R U . . .
C17 C 0.6482(4) -0.0949(3) 0.43443(19) 0.0450(8) Uani 1 1 d . . . . .
C18 C 0.7515(4) 0.0072(3) 0.39063(19) 0.0399(8) Uani 1 1 d . . . . .
H18 H 0.8409 0.0940 0.4205 0.048 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 1.978(2) . ?
Zn1 O4 1.980(2) 1_665 ?
Zn1 N2 2.035(2) . ?
Zn1 N1 2.037(2) . ?
O2 C19 1.238(3) . ?
O4 C20 1.280(3) . ?
O4 Zn1 1.980(2) 1_445 ?
O1 C19 1.281(3) . ?
O3 C20 1.228(3) . ?
O5 C17 1.372(4) . ?
O5 C21 1.436(4) . ?
N1 C1 1.339(4) . ?
N1 C5 1.340(4) . ?
N2 C11 1.335(4) . ?
N2 C7 1.336(4) . ?
C22 C21 1.491(4) . ?
C22 C23 1.522(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C19 C13 1.504(4) . ?
C23 C24 1.509(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C20 C15 1.508(4) . ?
C5 C4 1.381(4) . ?
C5 H5 0.9300 . ?
C14 C15 1.387(4) . ?
C14 C13 1.388(4) . ?
C14 H14 0.9300 . ?
C9 C8 1.380(4) . ?
C9 C10 1.391(4) . ?
C9 C12 1.463(4) . ?
C3 C4 1.381(4) . ?
C3 C2 1.392(4) . ?
C3 C6 1.464(4) . ?
C7 C8 1.375(4) . ?
C7 H7 0.9300 . ?
C12 C12 1.319(6) 2_665 ?
C12 H12 0.9300 . ?
C2 C1 1.380(4) . ?
C2 H2 0.9300 . ?
C6 C6 1.305(6) 2_855 ?
C6 H6 0.9300 . ?
C15 C16 1.387(4) . ?
C16 C17 1.385(4) . ?
C16 H16 0.9300 . ?
C8 H8 0.9300 . ?
C10 C11 1.367(4) . ?
C10 H10 0.9300 . ?
C4 H4 0.9300 . ?
C13 C18 1.393(4) . ?
C11 H11 0.9300 . ?
C1 H1 0.9300 . ?
C17 C18 1.374(4) . ?
C18 H18 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 O4 102.39(10) . 1_665 ?
O1 Zn1 N2 107.55(10) . . ?
O4 Zn1 N2 109.19(11) 1_665 . ?
O1 Zn1 N1 107.61(10) . . ?
O4 Zn1 N1 106.73(11) 1_665 . ?
N2 Zn1 N1 121.71(11) . . ?
C20 O4 Zn1 108.65(18) . 1_445 ?
C19 O1 Zn1 108.41(18) . . ?
C17 O5 C21 118.1(2) . . ?
C1 N1 C5 117.0(2) . . ?
C1 N1 Zn1 126.0(2) . . ?
C5 N1 Zn1 116.9(2) . . ?
C11 N2 C7 116.5(2) . . ?
C11 N2 Zn1 124.5(2) . . ?
C7 N2 Zn1 119.1(2) . . ?
C21 C22 C23 112.1(3) . . ?
C21 C22 H22A 109.2 . . ?
C23 C22 H22A 109.2 . . ?
C21 C22 H22B 109.2 . . ?
C23 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
O2 C19 O1 122.7(3) . . ?
O2 C19 C13 120.0(3) . . ?
O1 C19 C13 117.3(3) . . ?
C24 C23 C22 113.2(3) . . ?
C24 C23 H23A 108.9 . . ?
C22 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
C22 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O5 C21 C22 107.5(3) . . ?
O5 C21 H21A 110.2 . . ?
C22 C21 H21A 110.2 . . ?
O5 C21 H21B 110.2 . . ?
C22 C21 H21B 110.2 . . ?
H21A C21 H21B 108.5 . . ?
O3 C20 O4 123.4(3) . . ?
O3 C20 C15 119.6(3) . . ?
O4 C20 C15 117.1(3) . . ?
N1 C5 C4 122.6(3) . . ?
N1 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C15 C14 C13 120.9(3) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C8 C9 C10 116.8(3) . . ?
C8 C9 C12 120.0(3) . . ?
C10 C9 C12 123.2(3) . . ?
C4 C3 C2 117.2(3) . . ?
C4 C3 C6 119.6(3) . . ?
C2 C3 C6 123.2(3) . . ?
N2 C7 C8 122.9(3) . . ?
N2 C7 H7 118.5 . . ?
C8 C7 H7 118.5 . . ?
C12 C12 C9 126.0(4) 2_665 . ?
C12 C12 H12 117.0 2_665 . ?
C9 C12 H12 117.0 . . ?
C1 C2 C3 119.0(3) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C6 C6 C3 126.4(4) 2_855 . ?
C6 C6 H6 116.8 2_855 . ?
C3 C6 H6 116.8 . . ?
C16 C15 C14 119.0(3) . . ?
C16 C15 C20 120.7(3) . . ?
C14 C15 C20 120.3(3) . . ?
C17 C16 C15 120.4(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C7 C8 C9 120.3(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C11 C10 C9 119.1(3) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C14 C13 C18 119.2(3) . . ?
C14 C13 C19 120.6(3) . . ?
C18 C13 C19 120.1(3) . . ?
N2 C11 C10 124.3(3) . . ?
N2 C11 H11 117.8 . . ?
C10 C11 H11 117.8 . . ?
N1 C1 C2 123.8(3) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
O5 C17 C18 124.8(3) . . ?
O5 C17 C16 114.9(3) . . ?
C18 C17 C16 120.3(3) . . ?
C17 C18 C13 120.1(3) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.058

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1557105'
_audit_update_record             
;
2018-02-08 deposited with the CCDC.
2018-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 N O5 Zn'
_chemical_formula_sum            'C19 H19 N O5 Zn'
_chemical_formula_weight         406.72

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                   16.6370(16)
_cell_length_b                   9.2945(9)
_cell_length_c                   24.212(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.9500(10)
_cell_angle_gamma                90
_cell_volume                     3730.0(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3837
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      26.54

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_F_000             1680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.27
_exptl_absorpt_coefficient_mu    1.345
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10170
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.458
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             3295
_reflns_number_gt                2755
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0487P)²+1.1683P] 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         3278
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0848
_refine_ls_wR_factor_gt          0.0809
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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 0.06277(2) 0.46866(3) 0.18745(2) 0.02950(11) Uani 1 1 d . . . . .
O2 O -0.10815(11) 0.56643(19) 0.24402(7) 0.0389(4) Uani 1 1 d . . . . .
O3 O -0.35665(11) 0.8254(2) 0.17980(7) 0.0455(5) Uani 1 1 d . . . . .
O1 O -0.05169(9) 0.41756(19) 0.18628(7) 0.0362(4) Uani 1 1 d . . . . .
C13 C -0.10537(14) 0.5068(3) 0.19709(10) 0.0308(5) Uani 1 1 d . . . . .
O5 O -0.21545(12) 0.4590(3) 0.00743(8) 0.0617(6) Uani 1 1 d . . . . .
C7 C -0.16939(15) 0.5442(3) 0.15255(10) 0.0327(6) Uani 1 1 d . . . . .
O4 O -0.41451(12) 0.7931(2) 0.09486(8) 0.0548(5) Uani 1 1 d . . . . .
N1 N 0.05319(12) 0.6386(2) 0.13357(8) 0.0337(5) Uani 1 1 d . . . . .
C11 C -0.22491(17) 0.5203(3) 0.05768(11) 0.0430(7) Uani 1 1 d . . . . .
C6 C 0.00903(16) 1.0013(3) 0.02707(11) 0.0387(6) Uani 1 1 d . . . . .
H6 H 0.0129 1.0910 0.0441 0.046 Uiso 1 1 calc R U . . .
C12 C -0.16569(16) 0.4866(3) 0.10002(11) 0.0390(6) Uani 1 1 d . . . . .
H12 H -0.1236 0.4252 0.0930 0.047 Uiso 1 1 calc R U . . .
C8 C -0.23232(14) 0.6371(3) 0.16323(10) 0.0341(6) Uani 1 1 d . . . . .
H8 H -0.2348 0.6762 0.1984 0.041 Uiso 1 1 calc R U . . .
C9 C -0.29103(14) 0.6704(3) 0.12107(10) 0.0340(6) Uani 1 1 d . . . . .
C14 C -0.35993(16) 0.7698(3) 0.13143(11) 0.0386(6) Uani 1 1 d . . . . .
C10 C -0.28700(15) 0.6131(3) 0.06831(10) 0.0414(6) Uani 1 1 d . . . . .
H10 H -0.3261 0.6371 0.0400 0.050 Uiso 1 1 calc R U . . .
C3 C 0.02358(15) 0.8741(3) 0.06257(10) 0.0361(6) Uani 1 1 d . . . . .
C4 C 0.04686(19) 0.8915(3) 0.11855(11) 0.0490(7) Uani 1 1 d . . . . .
H4 H 0.0531 0.9835 0.1335 0.059 Uiso 1 1 calc R U . . .
C5 C 0.06070(18) 0.7735(3) 0.15191(11) 0.0473(7) Uani 1 1 d . . . . .
H5 H 0.0762 0.7884 0.1893 0.057 Uiso 1 1 calc R U . . .
C2 C 0.01587(18) 0.7336(3) 0.04349(11) 0.0486(7) Uani 1 1 d . . . . .
H2 H 0.0001 0.7161 0.0063 0.058 Uiso 1 1 calc R U . . .
C1 C 0.03136(18) 0.6204(3) 0.07926(10) 0.0458(7) Uani 1 1 d . . . . .
H1 H 0.0265 0.5273 0.0653 0.055 Uiso 1 1 calc R U . . .
C15 C -0.2793(2) 0.4799(4) -0.03504(12) 0.0613(9) Uani 1 1 d . . . . .
H15A H -0.2876 0.5821 -0.0413 0.074 Uiso 1 1 calc R U . . .
H15B H -0.3288 0.4397 -0.0232 0.074 Uiso 1 1 calc R U . . .
C16 C -0.26025(19) 0.4099(5) -0.08763(12) 0.0654(9) Uani 1 1 d . . . . .
H16A H -0.2535 0.3071 -0.0820 0.078 Uiso 1 1 calc R U . . .
H16B H -0.2104 0.4486 -0.0995 0.078 Uiso 1 1 calc R U . . .
C17 C -0.3308(2) 0.4391(5) -0.13259(14) 0.0810(12) Uani 1 1 d . . . . .
H17A H -0.3768 0.3820 -0.1237 0.097 Uiso 1 1 calc R U . . .
H17B H -0.3461 0.5395 -0.1302 0.097 Uiso 1 1 calc R U . . .
C18 C -0.3153(2) 0.4088(5) -0.18972(15) 0.0846(12) Uani 1 1 d . . . . .
H18A H -0.3064 0.3064 -0.1940 0.102 Uiso 1 1 calc R U . . .
H18B H -0.2669 0.4590 -0.1985 0.102 Uiso 1 1 calc R U . . .
C19 C -0.3858(3) 0.4561(5) -0.22942(18) 0.1072(17) Uani 1 1 d . . . . .
H19A H -0.3780 0.4223 -0.2661 0.161 Uiso 1 1 calc R U . . .
H19B H -0.3890 0.5592 -0.2297 0.161 Uiso 1 1 calc R U . . .
H19C H -0.4349 0.4167 -0.2177 0.161 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 O3 1.9094(17) 3_545 ?
Zn1 O1 1.9605(16) . ?
Zn1 O2 1.9831(17) 2 ?
Zn1 N1 2.0458(19) . ?
O2 C13 1.269(3) . ?
O2 Zn1 1.9831(17) 2 ?
O3 C14 1.277(3) . ?
O3 Zn1 1.9095(17) 3_455 ?
O1 C13 1.263(3) . ?
C13 C7 1.490(3) . ?
O5 C11 1.365(3) . ?
O5 C15 1.426(3) . ?
C7 C12 1.386(3) . ?
C7 C8 1.398(3) . ?
O4 C14 1.232(3) . ?
N1 C5 1.333(3) . ?
N1 C1 1.344(3) . ?
C11 C10 1.387(4) . ?
C11 C12 1.395(4) . ?
C6 C6 1.319(5) 5_575 ?
C6 C3 1.470(4) . ?
C6 H6 0.9300 . ?
C12 H12 0.9300 . ?
C8 C9 1.386(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.391(3) . ?
C9 C14 1.510(3) . ?
C10 H10 0.9300 . ?
C3 C4 1.387(3) . ?
C3 C2 1.387(4) . ?
C4 C5 1.370(4) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C2 C1 1.373(4) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?
C15 C16 1.488(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.555(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.456(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.515(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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
O3 Zn1 O1 121.25(8) 3_545 . ?
O3 Zn1 O2 100.42(8) 3_545 2 ?
O1 Zn1 O2 114.99(7) . 2 ?
O3 Zn1 N1 119.54(8) 3_545 . ?
O1 Zn1 N1 98.95(8) . . ?
O2 Zn1 N1 100.54(7) 2 . ?
C13 O2 Zn1 120.58(15) . 2 ?
C14 O3 Zn1 113.34(15) . 3_455 ?
C13 O1 Zn1 122.76(16) . . ?
O1 C13 O2 123.6(2) . . ?
O1 C13 C7 118.5(2) . . ?
O2 C13 C7 117.9(2) . . ?
C11 O5 C15 116.7(2) . . ?
C12 C7 C8 120.1(2) . . ?
C12 C7 C13 119.2(2) . . ?
C8 C7 C13 120.7(2) . . ?
C5 N1 C1 117.0(2) . . ?
C5 N1 Zn1 120.94(17) . . ?
C1 N1 Zn1 121.77(17) . . ?
O5 C11 C10 124.8(2) . . ?
O5 C11 C12 115.6(2) . . ?
C10 C11 C12 119.6(2) . . ?
C6 C6 C3 125.3(3) 5_575 . ?
C6 C6 H6 117.4 5_575 . ?
C3 C6 H6 117.4 . . ?
C7 C12 C11 120.2(2) . . ?
C7 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C9 C8 C7 119.6(2) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 120.3(2) . . ?
C8 C9 C14 120.8(2) . . ?
C10 C9 C14 119.0(2) . . ?
O4 C14 O3 124.0(2) . . ?
O4 C14 C9 120.7(2) . . ?
O3 C14 C9 115.3(2) . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C4 C3 C2 116.5(2) . . ?
C4 C3 C6 119.7(2) . . ?
C2 C3 C6 123.8(2) . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
N1 C5 C4 123.4(2) . . ?
N1 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
C1 C2 C3 120.3(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
N1 C1 C2 122.8(2) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
O5 C15 C16 110.9(3) . . ?
O5 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
O5 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.0 . . ?
C15 C16 C17 108.6(3) . . ?
C15 C16 H16A 110.0 . . ?
C17 C16 H16A 110.0 . . ?
C15 C16 H16B 110.0 . . ?
C17 C16 H16B 110.0 . . ?
H16A C16 H16B 108.4 . . ?
C18 C17 C16 116.5(3) . . ?
C18 C17 H17A 108.2 . . ?
C16 C17 H17A 108.2 . . ?
C18 C17 H17B 108.2 . . ?
C16 C17 H17B 108.2 . . ?
H17A C17 H17B 107.3 . . ?
C17 C18 C19 110.8(4) . . ?
C17 C18 H18A 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 C13 O2 -63.9(3) . . . . ?
Zn1 O1 C13 C7 116.4(2) . . . . ?
Zn1 O2 C13 O1 -27.8(3) 2 . . . ?
Zn1 O2 C13 C7 151.90(17) 2 . . . ?
O1 C13 C7 C12 -3.6(4) . . . . ?
O2 C13 C7 C12 176.7(2) . . . . ?
O1 C13 C7 C8 176.9(2) . . . . ?
O2 C13 C7 C8 -2.8(4) . . . . ?
C15 O5 C11 C10 -7.4(5) . . . . ?
C15 O5 C11 C12 173.8(3) . . . . ?
C8 C7 C12 C11 -0.3(4) . . . . ?
C13 C7 C12 C11 -179.9(2) . . . . ?
O5 C11 C12 C7 179.5(3) . . . . ?
C10 C11 C12 C7 0.7(4) . . . . ?
C12 C7 C8 C9 0.3(4) . . . . ?
C13 C7 C8 C9 179.8(2) . . . . ?
C7 C8 C9 C10 -0.6(4) . . . . ?
C7 C8 C9 C14 179.7(2) . . . . ?
Zn1 O3 C14 O4 -7.7(4) 3_455 . . . ?
Zn1 O3 C14 C9 172.33(17) 3_455 . . . ?
C8 C9 C14 O4 -175.9(3) . . . . ?
C10 C9 C14 O4 4.4(4) . . . . ?
C8 C9 C14 O3 4.0(4) . . . . ?
C10 C9 C14 O3 -175.6(2) . . . . ?
O5 C11 C10 C9 -179.7(3) . . . . ?
C12 C11 C10 C9 -1.0(4) . . . . ?
C8 C9 C10 C11 1.0(4) . . . . ?
C14 C9 C10 C11 -179.3(2) . . . . ?
C6 C6 C3 C4 176.2(3) 5_575 . . . ?
C6 C6 C3 C2 -3.5(5) 5_575 . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C6 C3 C4 C5 -179.9(3) . . . . ?
C1 N1 C5 C4 0.5(4) . . . . ?
Zn1 N1 C5 C4 -173.2(2) . . . . ?
C3 C4 C5 N1 0.1(5) . . . . ?
C4 C3 C2 C1 -0.3(4) . . . . ?
C6 C3 C2 C1 179.3(3) . . . . ?
C5 N1 C1 C2 -1.0(4) . . . . ?
Zn1 N1 C1 C2 172.6(2) . . . . ?
C3 C2 C1 N1 1.0(5) . . . . ?
C11 O5 C15 C16 178.9(3) . . . . ?
O5 C15 C16 C17 -178.7(3) . . . . ?
C15 C16 C17 C18 166.0(4) . . . . ?
C16 C17 C18 C19 -174.3(4) . . . . ?

_refine_diff_density_max         0.448
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.056

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1557103'
_audit_update_record             
;
2018-02-08 deposited with the CCDC.
2018-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H20 N2 O5 Zn, H2 O'
_chemical_formula_sum            'C23 H22 N2 O6 Zn'
_chemical_formula_weight         487.79

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                   9.5648(16)
_cell_length_b                   11.4815(16)
_cell_length_c                   11.5626(16)
_cell_angle_alpha                100.477(2)
_cell_angle_beta                 100.808(2)
_cell_angle_gamma                113.570(2)
_cell_volume                     1095.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2098
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      22.37

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    1.163
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8549
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.871
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.959
_reflns_number_total             3858
_reflns_number_gt                2889
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0466P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3803
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.0950
_refine_ls_wR_factor_gt          0.0872
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.18572(4) 0.87941(3) 0.12229(3) 0.03277(14) Uani 1 1 d . . . . .
O1 O 0.2793(2) 0.8181(2) 0.00614(19) 0.0411(5) Uani 1 1 d . . . . .
O3 O 0.9685(2) 0.8527(2) 0.0635(2) 0.0434(6) Uani 1 1 d . . . . .
O2 O 0.5164(3) 0.9380(2) 0.1427(2) 0.0542(7) Uani 1 1 d . . . . .
O5 O 0.3099(3) 0.4271(2) -0.2262(2) 0.0604(7) Uani 1 1 d . . . . .
O4 O 0.9134(3) 0.6527(3) -0.0457(3) 0.0741(9) Uani 1 1 d . . . . .
N1 N 0.2733(3) 1.0690(2) 0.2325(2) 0.0338(6) Uani 1 1 d . . . . .
N2 N 0.1772(3) 0.7638(2) 0.2412(2) 0.0385(6) Uani 1 1 d . . . . .
C7 C 0.4277(4) 0.8475(3) 0.0497(3) 0.0350(7) Uani 1 1 d . . . . .
C12 C 0.4293(4) 1.1493(3) 0.2880(3) 0.0422(8) Uani 1 1 d . . . . .
H12 H 0.5029 1.1188 0.2736 0.051 Uiso 1 1 calc R U . . .
C20 C 0.0762(4) 0.5870(3) 0.3802(3) 0.0423(8) Uani 1 1 d . . . . .
C2 C 0.6472(3) 0.7933(3) 0.0104(3) 0.0351(7) Uani 1 1 d . . . . .
H2 H 0.7211 0.8766 0.0620 0.042 Uiso 1 1 calc R U . . .
C8 C 0.8714(4) 0.7365(3) -0.0080(3) 0.0396(8) Uani 1 1 d . . . . .
C5 C 0.4275(4) 0.5463(3) -0.1483(3) 0.0428(8) Uani 1 1 d . . . . .
C1 C 0.4844(3) 0.7578(3) -0.0159(3) 0.0349(7) Uani 1 1 d . . . . .
C16 C 0.1715(4) 1.1162(3) 0.2541(3) 0.0409(8) Uani 1 1 d . . . . .
H16 H 0.0633 1.0622 0.2162 0.049 Uiso 1 1 calc R U . . .
C4 C 0.5883(4) 0.5801(3) -0.1195(3) 0.0407(8) Uani 1 1 d . . . . .
H4 H 0.6229 0.5201 -0.1527 0.049 Uiso 1 1 calc R U . . .
C3 C 0.6984(3) 0.7045(3) -0.0403(3) 0.0346(7) Uani 1 1 d . . . . .
C14 C 0.3771(4) 1.3232(3) 0.3882(3) 0.0368(8) Uani 1 1 d . . . . .
C6 C 0.3747(4) 0.6347(3) -0.0965(3) 0.0415(8) Uani 1 1 d . . . . .
H6 H 0.2664 0.6114 -0.1158 0.050 Uiso 1 1 calc R U . . .
C15 C 0.2175(4) 1.2403(3) 0.3292(3) 0.0417(8) Uani 1 1 d . . . . .
H15 H 0.1413 1.2687 0.3404 0.050 Uiso 1 1 calc R U . . .
C13 C 0.4843(4) 1.2745(3) 0.3648(3) 0.0438(8) Uani 1 1 d . . . . .
H13 H 0.5931 1.3268 0.4013 0.053 Uiso 1 1 calc R U . . .
C17 C 0.4265(4) 1.4551(3) 0.4684(3) 0.0423(8) Uani 1 1 d . . . . .
H17 H 0.3457 1.4789 0.4760 0.051 Uiso 1 1 calc R U . . .
C19 C 0.0745(4) 0.5435(3) 0.2604(3) 0.0440(9) Uani 1 1 d . . . . .
H19 H 0.0394 0.4538 0.2239 0.053 Uiso 1 1 calc R U . . .
C22 C 0.1877(4) 0.8064(3) 0.3602(3) 0.0468(9) Uani 1 1 d . . . . .
H22 H 0.2297 0.8971 0.3960 0.056 Uiso 1 1 calc R U . . .
C23 C 0.0055(4) 0.4875(4) 0.4451(3) 0.0479(9) Uani 1 1 d . . . . .
H23 H -0.0346 0.3987 0.4020 0.057 Uiso 1 1 calc R U . . .
C18 C 0.1247(4) 0.6332(3) 0.1952(3) 0.0434(8) Uani 1 1 d . . . . .
H18 H 0.1221 0.6015 0.1144 0.052 Uiso 1 1 calc R U . . .
C9 C 0.3544(4) 0.3264(3) -0.2711(3) 0.0459(9) Uani 1 1 d . . . . .
H9A H 0.4131 0.3103 -0.2030 0.055 Uiso 1 1 calc R U . . .
H9B H 0.4221 0.3546 -0.3235 0.055 Uiso 1 1 calc R U . . .
C21 C 0.1398(4) 0.7231(3) 0.4320(3) 0.0483(9) Uani 1 1 d . . . . .
H21 H 0.1498 0.7574 0.5141 0.058 Uiso 1 1 calc R U . . .
C10 C 0.2062(5) 0.2029(4) -0.3423(4) 0.0616(11) Uani 1 1 d . . . . .
H10A H 0.1457 0.2216 -0.4073 0.074 Uiso 1 1 calc R U . . .
H10B H 0.1410 0.1745 -0.2884 0.074 Uiso 1 1 calc R U . . .
C11 C 0.2418(5) 0.0920(4) -0.3981(4) 0.0766(13) Uani 1 1 d . . . . .
H11A H 0.2962 0.1158 -0.4583 0.115 Uiso 1 1 calc R U . . .
H11B H 0.1439 0.0124 -0.4366 0.115 Uiso 1 1 calc R U . . .
H11C H 0.3080 0.0773 -0.3348 0.115 Uiso 1 1 calc R U . . .
O1W O 0.8284(5) 0.1681(4) 0.2404(3) 0.0720(10) Uani 1 1 d . . . . .
H1WA H 0.767(5) 0.108(4) 0.228(4) 0.07(2) Uiso 1 1 d . . . . .
H1WB H 0.808(6) 0.192(5) 0.181(5) 0.10(2) Uiso 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
Zn1 O1 1.9264(19) . ?
Zn1 O3 1.938(2) 1_455 ?
Zn1 N1 2.048(2) . ?
Zn1 N2 2.068(3) . ?
O1 C7 1.292(3) . ?
O3 C8 1.283(4) . ?
O3 Zn1 1.938(2) 1_655 ?
O2 C7 1.226(4) . ?
O5 C5 1.375(4) . ?
O5 C9 1.430(4) . ?
O4 C8 1.225(4) . ?
N1 C16 1.330(4) . ?
N1 C12 1.347(4) . ?
N2 C22 1.344(4) . ?
N2 C18 1.338(4) . ?
C7 C1 1.500(4) . ?
C12 C13 1.374(4) . ?
C12 H12 0.9300 . ?
C20 C19 1.379(4) . ?
C20 C21 1.390(4) . ?
C20 C23 1.487(5) . ?
C2 C3 1.383(4) . ?
C2 C1 1.397(4) . ?
C2 H2 0.9300 . ?
C8 C3 1.498(4) . ?
C5 C6 1.395(4) . ?
C5 C4 1.382(4) . ?
C1 C6 1.391(4) . ?
C16 C15 1.373(4) . ?
C16 H16 0.9300 . ?
C4 C3 1.396(4) . ?
C4 H4 0.9300 . ?
C14 C15 1.383(4) . ?
C14 C13 1.395(4) . ?
C14 C17 1.460(4) . ?
C6 H6 0.9300 . ?
C15 H15 0.9300 . ?
C13 H13 0.9300 . ?
C17 C17 1.324(6) 2_686 ?
C17 H17 0.9300 . ?
C19 C18 1.372(4) . ?
C19 H19 0.9300 . ?
C22 C21 1.377(4) . ?
C22 H22 0.9300 . ?
C23 C23 1.283(6) 2_566 ?
C23 H23 0.9300 . ?
C18 H18 0.9300 . ?
C9 C10 1.493(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C21 H21 0.9300 . ?
C10 C11 1.511(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
O1W H1WA 0.67(4) . ?
O1W H1WB 0.80(5) . ?

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 O3 118.42(9) . 1_455 ?
O1 Zn1 N1 126.47(9) . . ?
O3 Zn1 N1 96.08(9) 1_455 . ?
O1 Zn1 N2 103.52(10) . . ?
O3 Zn1 N2 104.93(10) 1_455 . ?
N1 Zn1 N2 105.37(10) . . ?
C7 O1 Zn1 115.1(2) . . ?
C8 O3 Zn1 114.41(19) . 1_655 ?
C5 O5 C9 118.2(2) . . ?
C16 N1 C12 117.1(3) . . ?
C16 N1 Zn1 118.9(2) . . ?
C12 N1 Zn1 124.0(2) . . ?
C22 N2 C18 116.2(3) . . ?
C22 N2 Zn1 122.9(2) . . ?
C18 N2 Zn1 119.2(2) . . ?
O2 C7 O1 123.1(3) . . ?
O2 C7 C1 121.0(3) . . ?
O1 C7 C1 115.8(3) . . ?
N1 C12 C13 122.7(3) . . ?
N1 C12 H12 118.6 . . ?
C13 C12 H12 118.6 . . ?
C19 C20 C21 117.4(3) . . ?
C19 C20 C23 119.0(3) . . ?
C21 C20 C23 123.6(3) . . ?
C3 C2 C1 120.0(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
O4 C8 O3 123.3(3) . . ?
O4 C8 C3 120.4(3) . . ?
O3 C8 C3 116.3(3) . . ?
O5 C5 C6 115.5(3) . . ?
O5 C5 C4 124.2(3) . . ?
C6 C5 C4 120.4(3) . . ?
C6 C1 C2 119.7(3) . . ?
C6 C1 C7 120.0(3) . . ?
C2 C1 C7 120.1(3) . . ?
N1 C16 C15 123.5(3) . . ?
N1 C16 H16 118.2 . . ?
C15 C16 H16 118.2 . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C2 C3 C4 120.3(3) . . ?
C2 C3 C8 121.3(3) . . ?
C4 C3 C8 118.4(3) . . ?
C15 C14 C13 116.6(3) . . ?
C15 C14 C17 120.3(3) . . ?
C13 C14 C17 123.2(3) . . ?
C5 C6 C1 119.9(3) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C12 C13 C14 120.1(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C17 C17 C14 127.4(4) 2_686 . ?
C17 C17 H17 116.3 2_686 . ?
C14 C17 H17 116.3 . . ?
C18 C19 C20 119.7(3) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
N2 C22 C21 123.7(3) . . ?
N2 C22 H22 118.2 . . ?
C21 C22 H22 118.2 . . ?
C23 C23 C20 126.2(4) 2_566 . ?
C23 C23 H23 116.9 2_566 . ?
C20 C23 H23 116.9 . . ?
N2 C18 C19 123.7(3) . . ?
N2 C18 H18 118.2 . . ?
C19 C18 H18 118.2 . . ?
O5 C9 C10 108.3(3) . . ?
O5 C9 H9A 110.0 . . ?
C10 C9 H9A 110.0 . . ?
O5 C9 H9B 110.0 . . ?
C10 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
C22 C21 C20 119.1(3) . . ?
C22 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
C9 C10 C11 112.1(3) . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
H1WA O1W H1WB 103(5) . . ?

_refine_diff_density_max         0.402
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.064

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1557106'
_audit_update_record             
;
2018-02-08 deposited with the CCDC.
2018-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '	C20 H16 N2 O5 Zn, 2.5(H O0.50)'
_chemical_formula_sum            'C20 H20 N2 O7 Zn'
_chemical_formula_weight         465.75

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           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                   7.9207(7)
_cell_length_b                   15.0598(13)
_cell_length_c                   17.2160(14)
_cell_angle_alpha                90
_cell_angle_beta                 99.0770(10)
_cell_angle_gamma                90
_cell_volume                     2027.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4571
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      26.86

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.32
_exptl_absorpt_coefficient_mu    1.256
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11089
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.806
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             3566
_reflns_number_gt                3039
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0532P)²+0.4265P] 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         3546
_refine_ls_number_parameters     310
_refine_ls_number_restraints     52
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0923
_refine_ls_wR_factor_gt          0.0885
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.001
_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 0.20846(3) 0.85028(2) 0.18120(2) 0.03401(12) Uani 1 1 d . . . . .
O1 O 0.3735(2) 0.83133(12) 0.27688(10) 0.0455(4) Uani 1 1 d . . . . .
C13 C 0.7369(3) 0.77340(16) 0.47246(13) 0.0342(5) Uani 1 1 d . . . . .
O3 O 0.8046(2) 0.71590(14) 0.60135(10) 0.0510(5) Uani 1 1 d . . . . .
N2 N -0.6044(3) 0.47361(13) 0.31370(11) 0.0354(4) Uani 1 1 d . . . . .
O4 O 0.5634(3) 0.67163(13) 0.53080(11) 0.0556(5) Uani 1 1 d . . . . .
N1 N 0.0102(3) 0.77349(13) 0.21109(11) 0.0361(5) Uani 1 1 d . . . . .
C18 C 0.6972(3) 0.71558(16) 0.53804(14) 0.0378(6) Uani 1 1 d . . . . .
C11 C 0.6477(3) 0.85096(14) 0.35081(14) 0.0322(5) Uani 1 1 d . . . . .
C2 C -0.2820(3) 0.72583(16) 0.19444(14) 0.0371(6) Uani 1 1 d . . . . .
H2 H -0.3927 0.7312 0.1672 0.045 Uiso 1 1 calc R U . . .
C6 C -0.3790(3) 0.60517(15) 0.27843(14) 0.0340(5) Uani 1 1 d . . . . .
C3 C -0.2464(3) 0.66565(15) 0.25589(14) 0.0345(5) Uani 1 1 d . . . . .
C17 C 0.5137(3) 0.87407(17) 0.28198(14) 0.0383(6) Uani 1 1 d . . . . .
O2 O 0.5425(3) 0.93040(15) 0.23425(12) 0.0656(6) Uani 1 1 d . . . . .
C1 C -0.1515(3) 0.77776(16) 0.17406(15) 0.0394(6) Uani 1 1 d . . . . .
H1 H -0.1774 0.8176 0.1326 0.047 Uiso 1 1 calc R U . . .
C12 C 0.6124(3) 0.79183(15) 0.40860(13) 0.0322(5) Uani 1 1 d . . . . .
H12 H 0.5056 0.7649 0.4042 0.039 Uiso 1 1 calc R U . . .
C7 C -0.5243(3) 0.58255(17) 0.22582(15) 0.0413(6) Uani 1 1 d . . . . .
H7 H -0.5492 0.6119 0.1779 0.050 Uiso 1 1 calc R U . . .
C4 C -0.0785(4) 0.66198(17) 0.29501(17) 0.0474(7) Uani 1 1 d . . . . .
H4 H -0.0491 0.6230 0.3369 0.057 Uiso 1 1 calc R U . . .
C9 C -0.4727(3) 0.50040(16) 0.36676(15) 0.0417(6) Uani 1 1 d . . . . .
H9 H -0.4572 0.4742 0.4163 0.050 Uiso 1 1 calc R U . . .
C14 C 0.8991(3) 0.81092(18) 0.47745(15) 0.0451(6) Uani 1 1 d . . . . .
H14 H 0.9829 0.7981 0.5202 0.054 Uiso 1 1 calc R U . . .
C5 C 0.0431(3) 0.71628(17) 0.27139(16) 0.0466(6) Uani 1 1 d . . . . .
H5 H 0.1542 0.7133 0.2986 0.056 Uiso 1 1 calc R U . . .
C8 C -0.6315(3) 0.51651(17) 0.24473(15) 0.0420(6) Uani 1 1 d . . . . .
H8 H -0.7264 0.5012 0.2082 0.050 Uiso 1 1 calc R U . . .
C15 C 0.9354(4) 0.8673(2) 0.41880(18) 0.0519(7) Uani 1 1 d . . . . .
C10 C -0.3590(3) 0.56469(17) 0.35192(15) 0.0425(6) Uani 1 1 d . . . . .
H10 H -0.2692 0.5811 0.3908 0.051 Uiso 1 1 calc R U . . .
C16 C 0.8086(3) 0.88853(18) 0.35659(16) 0.0447(6) Uani 1 1 d . . . . .
H16 H 0.8318 0.9284 0.3184 0.054 Uiso 1 1 calc R U . . .
C19 C 1.2126(11) 0.9053(7) 0.4968(5) 0.060(2) Uani 0.5 1 d D U P A 1
H19A H 1.2476 0.8435 0.4975 0.072 Uiso 0.5 1 calc R U P A 1
H19B H 1.1705 0.9184 0.5455 0.072 Uiso 0.5 1 calc R U P A 1
C20 C 1.3594(8) 0.9646(5) 0.4876(5) 0.0705(19) Uani 0.5 1 d D U P A 1
H20A H 1.3989 0.9513 0.4390 0.106 Uiso 0.5 1 calc R U P A 1
H20B H 1.4506 0.9553 0.5306 0.106 Uiso 0.5 1 calc R U P A 1
H20C H 1.3230 1.0255 0.4872 0.106 Uiso 0.5 1 calc R U P A 1
C20' C 1.2390(14) 0.9335(6) 0.5347(6) 0.083(3) Uani 0.5 1 d D U P A 2
H20D H 1.2534 0.9939 0.5192 0.124 Uiso 0.5 1 calc R U P A 2
H20E H 1.3319 0.9171 0.5750 0.124 Uiso 0.5 1 calc R U P A 2
H20F H 1.1329 0.9279 0.5547 0.124 Uiso 0.5 1 calc R U P A 2
O5 O 1.0813(15) 0.9225(7) 0.4298(6) 0.059(2) Uani 0.5 1 d D U P A 1
C19' C 1.2370(10) 0.8755(6) 0.4672(5) 0.054(2) Uani 0.5 1 d D U P A 2
H19C H 1.3423 0.8828 0.4458 0.065 Uiso 0.5 1 calc R U P A 2
H19D H 1.2301 0.8141 0.4836 0.065 Uiso 0.5 1 calc R U P A 2
O5' O 1.0941(14) 0.8956(7) 0.4078(6) 0.057(2) Uani 0.5 1 d D U P A 2
O2W O 0.2619(12) 1.1423(7) 0.0502(6) 0.120(3) Uani 0.5 1 d G . P B 1
H2WA H 0.3181 1.1022 0.0305 0.180 Uiso 0.5 1 d G U P B 1
H2WB H 0.1624 1.1462 0.0234 0.180 Uiso 0.5 1 d G U P B 1
O1W O 0.0410(5) 0.4723(2) 0.4209(2) 0.1419(14) Uani 1 1 d . . . . .
H1WA H -0.0314 0.4415 0.4462 0.213 Uiso 1 1 d R U . . .
H1WB H 0.0626 0.4515 0.3777 0.213 Uiso 1 1 d R U . . .
O2W' O 0.3004(13) 1.1247(7) 0.0157(5) 0.101(3) Uiso 0.5 1 d G . P C 2
H2WC H 0.3080 1.0773 0.0429 0.152 Uiso 0.5 1 d G U P C 2
H2WD H 0.2318 1.1717 0.0317 0.152 Uiso 0.5 1 d G U P C 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
Zn1 O3 1.9475(17) 4_575 ?
Zn1 O1 1.9554(18) . ?
Zn1 N2 2.0396(19) 2_455 ?
Zn1 N1 2.079(2) . ?
O1 C17 1.275(3) . ?
C13 C12 1.384(3) . ?
C13 C14 1.394(4) . ?
C13 C18 1.498(3) . ?
O3 C18 1.272(3) . ?
O3 Zn1 1.9475(17) 4_676 ?
N2 C9 1.336(3) . ?
N2 C8 1.339(3) . ?
N2 Zn1 2.0396(19) 2_445 ?
O4 C18 1.239(3) . ?
N1 C1 1.339(3) . ?
N1 C5 1.343(3) . ?
C11 C16 1.383(4) . ?
C11 C12 1.396(3) . ?
C11 C17 1.502(3) . ?
C2 C1 1.385(4) . ?
C2 C3 1.388(3) . ?
C2 H2 0.9300 . ?
C6 C7 1.390(3) . ?
C6 C10 1.391(3) . ?
C6 C3 1.487(3) . ?
C3 C4 1.393(4) . ?
C17 O2 1.227(3) . ?
C1 H1 0.9300 . ?
C12 H12 0.9300 . ?
C7 C8 1.380(3) . ?
C7 H7 0.9300 . ?
C4 C5 1.373(4) . ?
C4 H4 0.9300 . ?
C9 C10 1.373(4) . ?
C9 H9 0.9300 . ?
C14 C15 1.384(4) . ?
C14 H14 0.9300 . ?
C5 H5 0.9300 . ?
C8 H8 0.9300 . ?
C15 O5' 1.369(12) . ?
C15 C16 1.385(4) . ?
C15 O5 1.412(12) . ?
C10 H10 0.9300 . ?
C16 H16 0.9300 . ?
C19 O5 1.449(12) . ?
C19 C20 1.495(9) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20' C19' 1.452(9) . ?
C20' H20D 0.9600 . ?
C20' H20E 0.9600 . ?
C20' H20F 0.9600 . ?
C19' O5' 1.433(12) . ?
C19' H19C 0.9700 . ?
C19' H19D 0.9700 . ?
O2W H2WA 0.8506 . ?
O2W H2WB 0.8500 . ?
O1W H1WA 0.9008 . ?
O1W H1WB 0.8497 . ?
O2W' H2WC 0.8501 . ?
O2W' H2WD 0.9587 . ?

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
O3 Zn1 O1 103.66(8) 4_575 . ?
O3 Zn1 N2 134.60(8) 4_575 2_455 ?
O1 Zn1 N2 108.52(8) . 2_455 ?
O3 Zn1 N1 106.53(8) 4_575 . ?
O1 Zn1 N1 98.10(8) . . ?
N2 Zn1 N1 99.76(8) 2_455 . ?
C17 O1 Zn1 116.34(16) . . ?
C12 C13 C14 120.1(2) . . ?
C12 C13 C18 120.5(2) . . ?
C14 C13 C18 119.4(2) . . ?
C18 O3 Zn1 108.65(16) . 4_676 ?
C9 N2 C8 117.4(2) . . ?
C9 N2 Zn1 121.53(16) . 2_445 ?
C8 N2 Zn1 117.90(16) . 2_445 ?
C1 N1 C5 117.0(2) . . ?
C1 N1 Zn1 123.94(16) . . ?
C5 N1 Zn1 119.07(17) . . ?
O4 C18 O3 122.3(2) . . ?
O4 C18 C13 120.8(2) . . ?
O3 C18 C13 116.9(2) . . ?
C16 C11 C12 119.7(2) . . ?
C16 C11 C17 119.4(2) . . ?
C12 C11 C17 120.9(2) . . ?
C1 C2 C3 119.4(2) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C7 C6 C10 116.7(2) . . ?
C7 C6 C3 121.8(2) . . ?
C10 C6 C3 121.5(2) . . ?
C2 C3 C4 117.3(2) . . ?
C2 C3 C6 122.1(2) . . ?
C4 C3 C6 120.6(2) . . ?
O2 C17 O1 123.7(2) . . ?
O2 C17 C11 120.4(2) . . ?
O1 C17 C11 115.9(2) . . ?
N1 C1 C2 123.3(2) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C13 C12 C11 119.7(2) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C8 C7 C6 120.0(2) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
N2 C9 C10 123.4(2) . . ?
N2 C9 H9 118.3 . . ?
C10 C9 H9 118.3 . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
N1 C5 C4 123.4(2) . . ?
N1 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
N2 C8 C7 122.5(2) . . ?
N2 C8 H8 118.7 . . ?
C7 C8 H8 118.7 . . ?
O5' C15 C14 126.4(5) . . ?
O5' C15 C16 113.0(5) . . ?
C14 C15 C16 119.8(2) . . ?
C14 C15 O5 121.5(5) . . ?
C16 C15 O5 116.5(5) . . ?
C9 C10 C6 119.6(2) . . ?
C9 C10 H10 120.2 . . ?
C6 C10 H10 120.2 . . ?
C11 C16 C15 120.6(2) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
O5 C19 C20 106.3(8) . . ?
O5 C19 H19A 110.5 . . ?
C20 C19 H19A 110.5 . . ?
O5 C19 H19B 110.5 . . ?
C20 C19 H19B 110.5 . . ?
H19A C19 H19B 108.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19' C20' H20D 109.5 . . ?
C19' C20' H20E 109.5 . . ?
H20D C20' H20E 109.5 . . ?
C19' C20' H20F 109.5 . . ?
H20D C20' H20F 109.5 . . ?
H20E C20' H20F 109.5 . . ?
C15 O5 C19 118.1(9) . . ?
O5' C19' C20' 110.5(8) . . ?
O5' C19' H19C 109.5 . . ?
C20' C19' H19C 109.5 . . ?
O5' C19' H19D 109.5 . . ?
C20' C19' H19D 109.5 . . ?
H19C C19' H19D 108.1 . . ?
C15 O5' C19' 118.4(9) . . ?
H2WA O2W H2WB 109.5 . . ?
H1WA O1W H1WB 117.6 . . ?
H2WC O2W' H2WD 117.2 . . ?

_refine_diff_density_max         0.655
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.053

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1557107'
_audit_update_record             
;
2018-02-08 deposited with the CCDC.
2018-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 N2 O5 Zn, 2(H2 O)'
_chemical_formula_sum            'C21 H22 N2 O7 Zn'
_chemical_formula_weight         479.77

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           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                   7.9431(7)
_cell_length_b                   15.5159(14)
_cell_length_c                   17.2037(16)
_cell_angle_alpha                90
_cell_angle_beta                 99.5690(10)
_cell_angle_gamma                90
_cell_volume                     2090.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4207
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      25.62

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    1.221
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11500
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.779
_diffrn_reflns_theta_max         25.006
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             3685
_reflns_number_gt                2965
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0424P)²+1.3119P] 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         3683
_refine_ls_number_parameters     321
_refine_ls_number_restraints     74
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0891
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_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 -1.80554(4) 0.85257(2) 0.18656(2) 0.03736(12) Uani 1 1 d . . . . .
O3 O -2.1403(3) 0.66705(13) -0.21768(11) 0.0500(5) Uani 1 1 d . . . . .
N1 N -2.0034(3) 0.78036(14) 0.21853(12) 0.0389(5) Uani 1 1 d . . . . .
N2 N -2.5957(3) 0.47294(14) 0.31027(12) 0.0379(5) Uani 1 1 d . . . . .
O2 O -1.9549(3) 0.82987(15) 0.03367(12) 0.0605(6) Uani 1 1 d . . . . .
C13 C -1.8653(3) 0.65208(16) -0.14286(14) 0.0338(6) Uani 1 1 d . . . . .
C12 C -1.9017(3) 0.71074(16) -0.08679(14) 0.0344(6) Uani 1 1 d . . . . .
H12 H -2.0087 0.7365 -0.0926 0.041 Uiso 1 1 calc R U . . .
O1 O -1.7133(3) 0.78868(15) 0.10627(11) 0.0560(6) Uani 1 1 d . . . . .
C4 C -2.2936(3) 0.73242(17) 0.20128(14) 0.0366(6) Uani 1 1 d . . . . .
H4 H -2.4050 0.7380 0.1746 0.044 Uiso 1 1 calc R U . . .
C6 C -2.3823(3) 0.60804(17) 0.28001(15) 0.0372(6) Uani 1 1 d . . . . .
C11 C -1.7788(3) 0.73083(17) -0.02232(14) 0.0367(6) Uani 1 1 d . . . . .
C18 C -1.9980(4) 0.62738(18) -0.21199(15) 0.0395(6) Uani 1 1 d . . . . .
O4 O -1.9665(3) 0.57237(15) -0.25895(13) 0.0625(6) Uani 1 1 d . . . . .
C17 C -1.8213(4) 0.78828(18) 0.04203(16) 0.0432(7) Uani 1 1 d . . . . .
C14 C -1.7041(3) 0.61619(18) -0.13519(16) 0.0414(6) Uani 1 1 d . . . . .
H14 H -1.6793 0.5769 -0.1725 0.050 Uiso 1 1 calc R U . . .
C15 C -1.5794(3) 0.63840(19) -0.07228(18) 0.0480(7) Uani 1 1 d D . . . .
C10 C -2.5202(4) 0.58196(19) 0.22435(17) 0.0474(7) Uani 1 1 d . . . . .
H10 H -2.5437 0.6097 0.1759 0.057 Uiso 1 1 calc R U . . .
C16 C -1.6157(3) 0.69521(19) -0.01554(16) 0.0450(7) Uani 1 1 d . . . . .
H16 H -1.5320 0.7096 0.0269 0.054 Uiso 1 1 calc R U . . .
C8 C -2.4709(4) 0.50215(18) 0.36592(16) 0.0444(7) Uani 1 1 d . . . . .
H8 H -2.4564 0.4767 0.4155 0.053 Uiso 1 1 calc R U . . .
C9 C -2.6216(4) 0.5152(2) 0.24109(17) 0.0485(7) Uani 1 1 d . . . . .
H9 H -2.7124 0.4983 0.2028 0.058 Uiso 1 1 calc R U . . .
C1 C -1.9666(4) 0.72211(19) 0.27686(17) 0.0469(7) Uani 1 1 d . . . . .
H1 H -1.8549 0.7188 0.3035 0.056 Uiso 1 1 calc R U . . .
C7 C -2.3629(4) 0.56808(18) 0.35327(16) 0.0452(7) Uani 1 1 d . . . . .
H7 H -2.2772 0.5859 0.3936 0.054 Uiso 1 1 calc R U . . .
C2 C -2.0856(4) 0.66746(18) 0.29882(17) 0.0479(7) Uani 1 1 d . . . . .
H2 H -2.0537 0.6281 0.3394 0.058 Uiso 1 1 calc R U . . .
C3 C -2.2545(3) 0.67071(16) 0.26047(15) 0.0370(6) Uani 1 1 d . . . . .
C5 C -2.1672(3) 0.78497(17) 0.18243(15) 0.0396(6) Uani 1 1 d . . . . .
H5 H -2.1961 0.8257 0.1428 0.047 Uiso 1 1 calc R U . . .
C20 C -1.1507(7) 0.5609(4) 0.0097(4) 0.0474(14) Uani 0.5 1 d D U P A 2
H20A H -1.1023 0.5748 -0.0369 0.057 Uiso 0.5 1 calc R U P A 2
H20B H -1.1829 0.5005 0.0069 0.057 Uiso 0.5 1 calc R U P A 2
C19 C -1.3069(8) 0.6156(5) 0.0117(4) 0.0478(16) Uani 0.5 1 d D U P A 2
H19A H -1.3558 0.6031 0.0585 0.057 Uiso 0.5 1 calc R U P A 2
H19B H -1.2778 0.6764 0.0119 0.057 Uiso 0.5 1 calc R U P A 2
C20' C -1.2476(12) 0.5705(5) 0.0410(4) 0.071(2) Uani 0.5 1 d D U P B 1
H20C H -1.2535 0.5104 0.0253 0.085 Uiso 0.5 1 calc R U P B 1
H20D H -1.3382 0.5813 0.0712 0.085 Uiso 0.5 1 calc R U P B 1
C19' C -1.2729(9) 0.6265(5) -0.0310(5) 0.0587(19) Uani 0.5 1 d D U P B 1
H19C H -1.2809 0.6862 -0.0153 0.070 Uiso 0.5 1 calc R U P B 1
H19D H -1.1746 0.6211 -0.0574 0.070 Uiso 0.5 1 calc R U P B 1
C21 C -1.0170(13) 0.5764(12) 0.0834(8) 0.063(3) Uani 0.5 1 d D U P A 2
H21A H -0.9197 0.5402 0.0817 0.094 Uiso 0.5 1 calc R U P A 2
H21B H -1.0653 0.5630 0.1296 0.094 Uiso 0.5 1 calc R U P A 2
H21C H -0.9822 0.6357 0.0852 0.094 Uiso 0.5 1 calc R U P A 2
C21' C -1.0733(12) 0.5885(12) 0.0930(8) 0.065(3) Uani 0.5 1 d D U P B 1
H21D H -0.9833 0.5694 0.0662 0.097 Uiso 0.5 1 calc R U P B 1
H21E H -1.0666 0.5581 0.1420 0.097 Uiso 0.5 1 calc R U P B 1
H21F H -1.0615 0.6492 0.1031 0.097 Uiso 0.5 1 calc R U P B 1
O5' O -1.4234(9) 0.6037(8) -0.0845(5) 0.059(3) Uani 0.5 1 d D U P B 1
O5 O -1.4256(10) 0.5942(9) -0.0582(5) 0.057(3) Uani 0.5 1 d D U P A 2
O1W O -2.0414(6) 0.5272(3) -0.4156(2) 0.1304(14) Uani 1 1 d G . . . .
H1WA H -1.9891 0.5662 -0.4368 0.196 Uiso 1 1 d G U . . .
H1WB H -2.0500 0.5421 -0.3689 0.196 Uiso 1 1 d G U . . .
O2W O -2.3068(5) 0.8750(3) -0.0200(3) 0.1518(17) Uani 1 1 d . . . . .
H2WA H -2.3522 0.9122 -0.0533 0.182 Uiso 1 1 d R U . . .
H2WB H -2.2240 0.8691 -0.0142 0.228 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 O1 1.940(2) . ?
Zn1 O3 1.9519(18) 4_676 ?
Zn1 N2 2.030(2) 2_055 ?
Zn1 N1 2.077(2) . ?
O3 C18 1.277(3) . ?
O3 Zn1 1.9518(18) 4_575 ?
N1 C1 1.346(3) . ?
N1 C5 1.347(3) . ?
N2 C8 1.337(3) . ?
N2 C9 1.344(3) . ?
N2 Zn1 2.030(2) 2_045 ?
O2 C17 1.230(3) . ?
C13 C14 1.383(4) . ?
C13 C12 1.391(4) . ?
C13 C18 1.501(4) . ?
C12 C11 1.386(3) . ?
C12 H12 0.9300 . ?
O1 C17 1.282(3) . ?
C4 C5 1.373(4) . ?
C4 C3 1.395(4) . ?
C4 H4 0.9300 . ?
C6 C10 1.390(4) . ?
C6 C7 1.390(4) . ?
C6 C3 1.484(4) . ?
C11 C16 1.395(4) . ?
C11 C17 1.503(4) . ?
C18 O4 1.229(3) . ?
C14 C15 1.384(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.381(4) . ?
C15 O5 1.386(8) . ?
C15 O5' 1.398(8) . ?
C10 C9 1.372(4) . ?
C10 H10 0.9300 . ?
C16 H16 0.9300 . ?
C8 C7 1.375(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C1 C2 1.369(4) . ?
C1 H1 0.9300 . ?
C7 H7 0.9300 . ?
C2 C3 1.395(4) . ?
C2 H2 0.9300 . ?
C5 H5 0.9300 . ?
C20 C19 1.509(7) . ?
C20 C21 1.532(9) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C19 O5 1.438(8) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20' C19' 1.499(7) . ?
C20' C21' 1.543(8) . ?
C20' H20C 0.9700 . ?
C20' H20D 0.9700 . ?
C19' O5' 1.427(8) . ?
C19' H19C 0.9700 . ?
C19' H19D 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C21' H21D 0.9600 . ?
C21' H21E 0.9600 . ?
C21' H21F 0.9600 . ?
O1W H1WA 0.8498 . ?
O1W H1WB 0.8500 . ?
O2W H2WA 0.8500 . ?
O2W H2WB 0.6551 . ?

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 O3 103.93(9) . 4_676 ?
O1 Zn1 N2 133.05(9) . 2_055 ?
O3 Zn1 N2 109.24(9) 4_676 2_055 ?
O1 Zn1 N1 107.76(9) . . ?
O3 Zn1 N1 97.15(9) 4_676 . ?
N2 Zn1 N1 100.15(9) 2_055 . ?
C18 O3 Zn1 116.88(18) . 4_575 ?
C1 N1 C5 116.9(2) . . ?
C1 N1 Zn1 118.64(18) . . ?
C5 N1 Zn1 124.37(18) . . ?
C8 N2 C9 117.0(2) . . ?
C8 N2 Zn1 122.43(18) . 2_045 ?
C9 N2 Zn1 117.99(18) . 2_045 ?
C14 C13 C12 119.5(2) . . ?
C14 C13 C18 119.3(2) . . ?
C12 C13 C18 121.1(2) . . ?
C11 C12 C13 120.2(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C17 O1 Zn1 109.78(19) . . ?
C5 C4 C3 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C10 C6 C7 116.8(3) . . ?
C10 C6 C3 121.7(2) . . ?
C7 C6 C3 121.4(2) . . ?
C12 C11 C16 119.9(2) . . ?
C12 C11 C17 120.6(2) . . ?
C16 C11 C17 119.5(2) . . ?
O4 C18 O3 124.0(3) . . ?
O4 C18 C13 120.3(3) . . ?
O3 C18 C13 115.7(2) . . ?
O2 C17 O1 122.6(3) . . ?
O2 C17 C11 121.3(2) . . ?
O1 C17 C11 116.0(3) . . ?
C13 C14 C15 120.4(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 O5 118.2(4) . . ?
C14 C15 O5 120.6(5) . . ?
C16 C15 O5' 130.3(5) . . ?
C14 C15 O5' 108.9(4) . . ?
C9 C10 C6 119.9(3) . . ?
C9 C10 H10 120.1 . . ?
C6 C10 H10 120.1 . . ?
C15 C16 C11 119.6(2) . . ?
C15 C16 H16 120.2 . . ?
C11 C16 H16 120.2 . . ?
N2 C8 C7 123.1(3) . . ?
N2 C8 H8 118.4 . . ?
C7 C8 H8 118.4 . . ?
N2 C9 C10 123.0(3) . . ?
N2 C9 H9 118.5 . . ?
C10 C9 H9 118.5 . . ?
N1 C1 C2 123.2(2) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C8 C7 C6 119.8(2) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C1 C2 C3 120.1(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 116.8(2) . . ?
C2 C3 C6 120.6(2) . . ?
C4 C3 C6 122.5(2) . . ?
N1 C5 C4 123.2(2) . . ?
N1 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?
C19 C20 C21 110.6(6) . . ?
C19 C20 H20A 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
O5 C19 C20 106.2(6) . . ?
O5 C19 H19A 110.5 . . ?
C20 C19 H19A 110.5 . . ?
O5 C19 H19B 110.5 . . ?
C20 C19 H19B 110.5 . . ?
H19A C19 H19B 108.7 . . ?
C19' C20' C21' 111.0(9) . . ?
C19' C20' H20C 109.4 . . ?
C21' C20' H20C 109.4 . . ?
C19' C20' H20D 109.4 . . ?
C21' C20' H20D 109.4 . . ?
H20C C20' H20D 108.0 . . ?
O5' C19' C20' 111.9(7) . . ?
O5' C19' H19C 109.2 . . ?
C20' C19' H19C 109.2 . . ?
O5' C19' H19D 109.2 . . ?
C20' C19' H19D 109.2 . . ?
H19C C19' H19D 107.9 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20' C21' H21D 109.5 . . ?
C20' C21' H21E 109.5 . . ?
H21D C21' H21E 109.5 . . ?
C20' C21' H21F 109.5 . . ?
H21D C21' H21F 109.5 . . ?
H21E C21' H21F 109.5 . . ?
C15 O5' C19' 118.4(8) . . ?
C15 O5 C19 117.9(8) . . ?
H1WA O1W H1WB 109.5 . . ?
H2WA O2W H2WB 120.0 . . ?

_refine_diff_density_max         0.457
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.060

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1557108'
_audit_update_record             
;
2018-02-08 deposited with the CCDC.
2018-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 N2 O5 Zn'
_chemical_formula_sum            'C22 H20 N2 O5 Zn'
_chemical_formula_weight         457.77

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.5909(16)
_cell_length_b                   15.3382(18)
_cell_length_c                   19.411(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4046.4(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2175
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      19.72

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_F_000             1888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    1.251
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26406
_diffrn_reflns_av_unetI/netI     0.0751
_diffrn_reflns_av_R_equivalents  0.0898
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.098
_diffrn_reflns_theta_max         28.392
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5078
_reflns_number_gt                2612
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0464P)²] 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         4909
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1153
_refine_ls_wR_factor_gt          0.0914
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_restrained_S_all      0.987
_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 0.19883(3) 0.27646(2) 0.25482(2) 0.03247(13) Uani 1 1 d . . . . .
O1 O 0.10978(17) 0.24280(16) 0.18173(11) 0.0474(7) Uani 1 1 d . . . . .
O4 O 0.07813(18) 0.14991(16) -0.17726(11) 0.0513(7) Uani 1 1 d . . . . .
O5 O -0.12656(18) 0.08486(17) 0.03923(11) 0.0550(7) Uani 1 1 d . . . . .
O2 O 0.2134(2) 0.3085(2) 0.11205(13) 0.0858(11) Uani 1 1 d . . . . .
O3 O 0.17557(18) 0.25517(16) -0.14459(11) 0.0475(7) Uani 1 1 d . . . . .
N1 N 0.29795(19) 0.37861(18) 0.25809(12) 0.0364(6) Uani 1 1 d . . . . .
N2 N 0.69040(19) 0.68002(18) 0.25529(13) 0.0364(6) Uani 1 1 d . . . . .
C22 C -0.4012(4) -0.1155(4) -0.0013(2) 0.123(2) Uani 1 1 d . . . . .
H22A H -0.4348 -0.1469 -0.0370 0.185 Uiso 1 1 calc R U . . .
H22B H -0.4472 -0.0791 0.0228 0.185 Uiso 1 1 calc R U . . .
H22C H -0.3721 -0.1560 0.0303 0.185 Uiso 1 1 calc R U . . .
C12 C 0.1200(2) 0.2345(2) -0.00556(14) 0.0332(8) Uani 1 1 d . . . . .
H12 H 0.1743 0.2697 -0.0145 0.040 Uiso 1 1 calc R U . . .
C14 C -0.0106(2) 0.1412(2) -0.04617(15) 0.0367(8) Uani 1 1 d . . . . .
H14 H -0.0420 0.1128 -0.0823 0.044 Uiso 1 1 calc R U . . .
C8 C 0.5351(2) 0.5610(2) 0.26092(15) 0.0335(8) Uani 1 1 d . . . . .
C3 C 0.4511(2) 0.4991(2) 0.26165(15) 0.0356(8) Uani 1 1 d . . . . .
C19 C -0.1782(3) 0.0389(2) -0.01324(17) 0.0458(10) Uani 1 1 d . . . . .
H19A H -0.1348 -0.0027 -0.0354 0.055 Uiso 1 1 calc R U . . .
H19B H -0.2019 0.0793 -0.0479 0.055 Uiso 1 1 calc R U . . .
C13 C 0.0719(2) 0.1919(2) -0.05888(15) 0.0308(8) Uani 1 1 d . . . . .
C15 C -0.0462(2) 0.1330(2) 0.02029(16) 0.0365(8) Uani 1 1 d . . . . .
C17 C 0.1400(3) 0.2636(2) 0.12187(17) 0.0411(9) Uani 1 1 d . . . . .
C1 C 0.3049(3) 0.4419(2) 0.21136(17) 0.0420(8) Uani 1 1 d . . . . .
H1 H 0.2571 0.4455 0.1772 0.050 Uiso 1 1 calc R U . . .
C11 C 0.0857(2) 0.2237(2) 0.06200(15) 0.0323(7) Uani 1 1 d . . . . .
C18 C 0.1102(2) 0.1988(2) -0.13156(16) 0.0346(8) Uani 1 1 d . . . . .
C16 C 0.0028(2) 0.1747(2) 0.07421(15) 0.0369(8) Uani 1 1 d . . . . .
H16 H -0.0209 0.1692 0.1189 0.044 Uiso 1 1 calc R U . . .
C10 C 0.6215(3) 0.6842(3) 0.30459(18) 0.0510(10) Uani 1 1 d . . . . .
H10 H 0.6266 0.7280 0.3375 0.061 Uiso 1 1 calc R U . . .
C6 C 0.6817(2) 0.6157(2) 0.20902(17) 0.0402(8) Uani 1 1 d . . . . .
H6 H 0.7287 0.6115 0.1744 0.048 Uiso 1 1 calc R U . . .
C4 C 0.4431(3) 0.4347(3) 0.31056(19) 0.0611(12) Uani 1 1 d . . . . .
H4 H 0.4890 0.4309 0.3460 0.073 Uiso 1 1 calc R U . . .
C2 C 0.3797(3) 0.5021(2) 0.21147(17) 0.0441(9) Uani 1 1 d . . . . .
H2 H 0.3822 0.5449 0.1776 0.053 Uiso 1 1 calc R U . . .
C9 C 0.5436(3) 0.6270(3) 0.30901(18) 0.0520(10) Uani 1 1 d . . . . .
H9 H 0.4972 0.6327 0.3439 0.062 Uiso 1 1 calc R U . . .
C7 C 0.6066(3) 0.5557(2) 0.21034(17) 0.0422(9) Uani 1 1 d . . . . .
H7 H 0.6039 0.5118 0.1774 0.051 Uiso 1 1 calc R U . . .
C20 C -0.2632(3) -0.0078(2) 0.01941(19) 0.0541(11) Uani 1 1 d . . . . .
H20A H -0.3061 0.0344 0.0414 0.065 Uiso 1 1 calc R U . . .
H20B H -0.2388 -0.0469 0.0547 0.065 Uiso 1 1 calc R U . . .
C5 C 0.3670(3) 0.3759(3) 0.30691(18) 0.0590(12) Uani 1 1 d . . . . .
H5 H 0.3634 0.3322 0.3400 0.071 Uiso 1 1 calc R U . . .
C21 C -0.3216(3) -0.0595(3) -0.0329(2) 0.0723(13) Uani 1 1 d . . . . .
H21A H -0.3516 -0.0193 -0.0653 0.087 Uiso 1 1 calc R U . . .
H21B H -0.2769 -0.0966 -0.0585 0.087 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 1.935(2) . ?
Zn1 O3 2.037(2) 8_566 ?
Zn1 N1 2.067(3) . ?
Zn1 N2 2.120(3) 4_645 ?
Zn1 O4 2.388(2) 8_566 ?
Zn1 C18 2.542(3) 8_566 ?
O1 C17 1.273(4) . ?
O4 C18 1.240(4) . ?
O4 Zn1 2.388(2) 8_565 ?
O5 C15 1.369(4) . ?
O5 C19 1.424(4) . ?
O2 C17 1.227(4) . ?
O3 C18 1.266(4) . ?
O3 Zn1 2.037(2) 8_565 ?
N1 C1 1.332(4) . ?
N1 C5 1.334(4) . ?
N2 C6 1.339(4) . ?
N2 C10 1.340(4) . ?
N2 Zn1 2.120(3) 4_655 ?
C22 C21 1.511(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C12 C13 1.388(4) . ?
C12 C11 1.402(4) . ?
C12 H12 0.9300 . ?
C14 C15 1.384(4) . ?
C14 C13 1.386(4) . ?
C14 H14 0.9300 . ?
C8 C9 1.382(4) . ?
C8 C7 1.384(4) . ?
C8 C3 1.485(5) . ?
C3 C4 1.374(4) . ?
C3 C2 1.375(4) . ?
C19 C20 1.499(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C13 C18 1.508(4) . ?
C15 C16 1.395(4) . ?
C17 C11 1.506(4) . ?
C1 C2 1.373(5) . ?
C1 H1 0.9300 . ?
C11 C16 1.376(4) . ?
C18 Zn1 2.542(3) 8_565 ?
C16 H16 0.9300 . ?
C10 C9 1.379(5) . ?
C10 H10 0.9300 . ?
C6 C7 1.374(4) . ?
C6 H6 0.9300 . ?
C4 C5 1.374(5) . ?
C4 H4 0.9300 . ?
C2 H2 0.9300 . ?
C9 H9 0.9300 . ?
C7 H7 0.9300 . ?
C20 C21 1.513(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C5 H5 0.9300 . ?
C21 H21A 0.9700 . ?
C21 H21B 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
O1 Zn1 O3 122.84(10) . 8_566 ?
O1 Zn1 N1 129.22(10) . . ?
O3 Zn1 N1 104.61(10) 8_566 . ?
O1 Zn1 N2 100.96(10) . 4_645 ?
O3 Zn1 N2 91.88(10) 8_566 4_645 ?
N1 Zn1 N2 93.95(11) . 4_645 ?
O1 Zn1 O4 95.82(9) . 8_566 ?
O3 Zn1 O4 58.46(9) 8_566 8_566 ?
N1 Zn1 O4 94.14(10) . 8_566 ?
N2 Zn1 O4 150.33(9) 4_645 8_566 ?
O1 Zn1 C18 112.32(10) . 8_566 ?
O3 Zn1 C18 29.56(10) 8_566 8_566 ?
N1 Zn1 C18 99.72(10) . 8_566 ?
N2 Zn1 C18 121.42(11) 4_645 8_566 ?
O4 Zn1 C18 28.93(9) 8_566 8_566 ?
C17 O1 Zn1 113.6(2) . . ?
C18 O4 Zn1 82.4(2) . 8_565 ?
C15 O5 C19 117.9(2) . . ?
C18 O3 Zn1 97.9(2) . 8_565 ?
C1 N1 C5 117.1(3) . . ?
C1 N1 Zn1 125.3(2) . . ?
C5 N1 Zn1 117.2(2) . . ?
C6 N2 C10 116.9(3) . . ?
C6 N2 Zn1 121.0(2) . 4_655 ?
C10 N2 Zn1 121.9(2) . 4_655 ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C13 C12 C11 119.1(3) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C9 C8 C7 117.6(3) . . ?
C9 C8 C3 121.7(3) . . ?
C7 C8 C3 120.7(3) . . ?
C4 C3 C2 117.2(3) . . ?
C4 C3 C8 121.8(3) . . ?
C2 C3 C8 121.0(3) . . ?
O5 C19 C20 108.3(3) . . ?
O5 C19 H19A 110.0 . . ?
C20 C19 H19A 110.0 . . ?
O5 C19 H19B 110.0 . . ?
C20 C19 H19B 110.0 . . ?
H19A C19 H19B 108.4 . . ?
C14 C13 C12 120.8(3) . . ?
C14 C13 C18 119.0(3) . . ?
C12 C13 C18 120.1(3) . . ?
O5 C15 C14 125.4(3) . . ?
O5 C15 C16 115.2(3) . . ?
C14 C15 C16 119.4(3) . . ?
O2 C17 O1 123.0(3) . . ?
O2 C17 C11 120.4(3) . . ?
O1 C17 C11 116.4(3) . . ?
N1 C1 C2 122.8(3) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C16 C11 C12 119.9(3) . . ?
C16 C11 C17 119.4(3) . . ?
C12 C11 C17 120.8(3) . . ?
O4 C18 O3 121.1(3) . . ?
O4 C18 C13 120.4(3) . . ?
O3 C18 C13 118.5(3) . . ?
O4 C18 Zn1 68.67(18) . 8_565 ?
O3 C18 Zn1 52.54(16) . 8_565 ?
C13 C18 Zn1 170.5(2) . 8_565 ?
C11 C16 C15 120.8(3) . . ?
C11 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
N2 C10 C9 123.4(3) . . ?
N2 C10 H10 118.3 . . ?
C9 C10 H10 118.3 . . ?
N2 C6 C7 123.1(3) . . ?
N2 C6 H6 118.4 . . ?
C7 C6 H6 118.4 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C1 C2 C3 120.1(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C10 C9 C8 119.3(3) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C6 C7 C8 119.7(3) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C19 C20 C21 111.7(3) . . ?
C19 C20 H20A 109.3 . . ?
C21 C20 H20A 109.3 . . ?
C19 C20 H20B 109.3 . . ?
C21 C20 H20B 109.3 . . ?
H20A C20 H20B 107.9 . . ?
N1 C5 C4 123.1(3) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
C22 C21 C20 113.6(4) . . ?
C22 C21 H21A 108.8 . . ?
C20 C21 H21A 108.8 . . ?
C22 C21 H21B 108.8 . . ?
C20 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?

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
C9 C8 C3 C4 -73.1(5) . . . . ?
C7 C8 C3 C4 108.8(4) . . . . ?
C9 C8 C3 C2 109.4(4) . . . . ?
C7 C8 C3 C2 -68.7(5) . . . . ?
C15 O5 C19 C20 -179.3(3) . . . . ?
C15 C14 C13 C12 0.3(5) . . . . ?
C15 C14 C13 C18 179.1(3) . . . . ?
C11 C12 C13 C14 1.8(5) . . . . ?
C11 C12 C13 C18 -177.0(3) . . . . ?
C19 O5 C15 C14 0.2(5) . . . . ?
C19 O5 C15 C16 -178.4(3) . . . . ?
C13 C14 C15 O5 -179.8(3) . . . . ?
C13 C14 C15 C16 -1.2(5) . . . . ?
Zn1 O1 C17 O2 -7.0(5) . . . . ?
Zn1 O1 C17 C11 167.8(2) . . . . ?
C5 N1 C1 C2 0.8(5) . . . . ?
Zn1 N1 C1 C2 -171.8(3) . . . . ?
C13 C12 C11 C16 -2.9(5) . . . . ?
C13 C12 C11 C17 175.7(3) . . . . ?
O2 C17 C11 C16 -179.1(4) . . . . ?
O1 C17 C11 C16 5.9(5) . . . . ?
O2 C17 C11 C12 2.3(5) . . . . ?
O1 C17 C11 C12 -172.7(3) . . . . ?
Zn1 O4 C18 O3 3.2(3) 8_565 . . . ?
Zn1 O4 C18 C13 -176.7(3) 8_565 . . . ?
Zn1 O3 C18 O4 -3.7(3) 8_565 . . . ?
Zn1 O3 C18 C13 176.2(2) 8_565 . . . ?
C14 C13 C18 O4 -10.9(5) . . . . ?
C12 C13 C18 O4 167.9(3) . . . . ?
C14 C13 C18 O3 169.2(3) . . . . ?
C12 C13 C18 O3 -12.0(5) . . . . ?
C12 C11 C16 C15 2.0(5) . . . . ?
C17 C11 C16 C15 -176.6(3) . . . . ?
O5 C15 C16 C11 178.8(3) . . . . ?
C14 C15 C16 C11 0.1(5) . . . . ?
C6 N2 C10 C9 -0.7(5) . . . . ?
Zn1 N2 C10 C9 174.1(3) 4_655 . . . ?
C10 N2 C6 C7 0.1(5) . . . . ?
Zn1 N2 C6 C7 -174.8(2) 4_655 . . . ?
C2 C3 C4 C5 1.2(6) . . . . ?
C8 C3 C4 C5 -176.4(4) . . . . ?
N1 C1 C2 C3 -0.6(6) . . . . ?
C4 C3 C2 C1 -0.4(5) . . . . ?
C8 C3 C2 C1 177.2(3) . . . . ?
N2 C10 C9 C8 0.5(6) . . . . ?
C7 C8 C9 C10 0.2(5) . . . . ?
C3 C8 C9 C10 -178.0(3) . . . . ?
N2 C6 C7 C8 0.6(5) . . . . ?
C9 C8 C7 C6 -0.7(5) . . . . ?
C3 C8 C7 C6 177.5(3) . . . . ?
O5 C19 C20 C21 -179.3(3) . . . . ?
C1 N1 C5 C4 0.0(6) . . . . ?
Zn1 N1 C5 C4 173.2(3) . . . . ?
C3 C4 C5 N1 -1.1(7) . . . . ?
C19 C20 C21 C22 173.6(4) . . . . ?

_refine_diff_density_max         0.343
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.078

_shelxl_version_number           2014-3

