# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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 1038879'
_audit_update_record             
;
2014-12-11 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

#========================================================================== 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 N O4 Zn, H2 O'
_chemical_formula_sum            'C15 H12 N O5 Zn'
_chemical_formula_weight         351.65

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   9.1087(18)
_cell_length_b                   14.849(3)
_cell_length_c                   10.894(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.38(3)
_cell_angle_gamma                90.00
_cell_volume                     1420.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             716
_exptl_absorpt_coefficient_mu    1.752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6041
_exptl_absorpt_correction_T_max  0.6685
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_special_details           
; 
 ?  
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5846
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         25.05
_reflns_number_total             2501
_reflns_number_gt                2007
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    Diamond
_computing_publication_material  'SHELXTL and PLATON (Spek, 2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0364P)²+2.6904P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2501
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1019
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.35895(4) -0.00331(3) 0.39134(3) 0.01146(15) Uani 1 1 d . . .
N1 N 0.1475(3) -0.0174(2) 0.2725(3) 0.0167(7) Uani 1 1 d . . .
O1 O 0.4510(3) 0.1021(2) 0.3159(3) 0.0340(7) Uani 1 1 d . . .
O2 O 0.6531(3) 0.1048(2) 0.4827(3) 0.0348(8) Uani 1 1 d . . .
O3 O 0.8115(3) 0.4153(2) 0.0188(3) 0.0309(7) Uani 1 1 d . . .
O4 O 1.0158(3) 0.4109(2) 0.1837(2) 0.0339(8) Uani 1 1 d . . .
O5 O 0.1780(7) 0.2148(4) 0.1681(6) 0.128(2) Uani 1 1 d . . .
H1W H 0.1581 0.2568 0.1130 0.191 Uiso 1 1 d R . .
H2W H 0.2301 0.2067 0.2445 0.191 Uiso 1 1 d R . .
C1 C 0.0347(5) 0.0350(3) 0.2872(5) 0.0420(13) Uani 1 1 d . . .
H1 H 0.0562 0.0769 0.3543 0.050 Uiso 1 1 calc R . .
C2 C -0.1108(5) 0.0313(4) 0.2099(5) 0.0455(14) Uani 1 1 d . . .
H2 H -0.1855 0.0704 0.2247 0.055 Uiso 1 1 calc R . .
C3 C -0.1487(4) -0.0297(3) 0.1102(3) 0.0188(8) Uani 1 1 d . . .
C4 C -0.0305(4) -0.0845(3) 0.0952(3) 0.0205(8) Uani 1 1 d . . .
H4 H -0.0489 -0.1271 0.0289 0.025 Uiso 1 1 calc R . .
C5 C 0.1124(4) -0.0768(3) 0.1765(3) 0.0196(8) Uani 1 1 d . . .
H5 H 0.1896 -0.1150 0.1642 0.024 Uiso 1 1 calc R . .
C6 C -0.3003(4) -0.0346(3) 0.0228(4) 0.0219(9) Uani 1 1 d . . .
H6 H -0.3110 -0.0665 -0.0536 0.026 Uiso 1 1 calc R . .
C7 C -0.4260(4) 0.0030(3) 0.0432(4) 0.0219(9) Uani 1 1 d . . .
H7 H -0.4158 0.0352 0.1193 0.026 Uiso 1 1 calc R . .
C8 C 0.6546(4) 0.2000(2) 0.3112(3) 0.0170(8) Uani 1 1 d . . .
C9 C 0.5832(4) 0.2324(3) 0.1915(4) 0.0244(9) Uani 1 1 d . . .
H9 H 0.4838 0.2135 0.1503 0.029 Uiso 1 1 calc R . .
C10 C 0.6583(4) 0.2929(3) 0.1319(4) 0.0246(9) Uani 1 1 d . . .
H10 H 0.6091 0.3148 0.0504 0.030 Uiso 1 1 calc R . .
C11 C 0.8052(4) 0.3212(2) 0.1915(3) 0.0174(8) Uani 1 1 d . . .
C12 C 0.8760(4) 0.2888(3) 0.3119(3) 0.0191(8) Uani 1 1 d . . .
H12 H 0.9752 0.3076 0.3534 0.023 Uiso 1 1 calc R . .
C13 C 0.8008(4) 0.2286(3) 0.3710(3) 0.0193(8) Uani 1 1 d . . .
H13 H 0.8496 0.2070 0.4528 0.023 Uiso 1 1 calc R . .
C14 C 0.5800(4) 0.1307(2) 0.3754(3) 0.0175(8) Uani 1 1 d . . .
C15 C 0.8841(4) 0.3872(3) 0.1263(3) 0.0189(8) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O4 2.021(3) 2_645 ?
Zn1 N1 2.027(3) . ?
Zn1 O3 2.035(3) 4_566 ?
Zn1 O1 2.047(3) . ?
Zn1 O2 2.061(3) 3_656 ?
Zn1 Zn1 2.9983(13) 3_656 ?
N1 C1 1.333(5) . ?
N1 C5 1.340(5) . ?
O1 C14 1.256(5) . ?
O2 C14 1.243(4) . ?
O2 Zn1 2.061(3) 3_656 ?
O3 C15 1.255(4) . ?
O3 Zn1 2.035(3) 4_665 ?
O4 C15 1.248(5) . ?
O4 Zn1 2.021(3) 2_655 ?
C1 C2 1.370(6) . ?
C2 C3 1.386(6) . ?
C3 C4 1.394(5) . ?
C3 C6 1.456(5) . ?
C4 C5 1.372(5) . ?
C6 C7 1.344(5) . ?
C7 C7 1.428(8) 3_455 ?
C8 C9 1.380(5) . ?
C8 C13 1.385(5) . ?
C8 C14 1.504(5) . ?
C9 C10 1.390(5) . ?
C10 C11 1.389(5) . ?
C11 C12 1.385(5) . ?
C11 C15 1.500(5) . ?
C12 C13 1.384(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
O4 Zn1 N1 102.66(12) 2_645 . ?
O4 Zn1 O3 157.71(12) 2_645 4_566 ?
N1 Zn1 O3 99.47(11) . 4_566 ?
O4 Zn1 O1 89.09(14) 2_645 . ?
N1 Zn1 O1 104.10(12) . . ?
O3 Zn1 O1 88.07(13) 4_566 . ?
O4 Zn1 O2 86.78(13) 2_645 3_656 ?
N1 Zn1 O2 98.06(12) . 3_656 ?
O3 Zn1 O2 87.55(13) 4_566 3_656 ?
O1 Zn1 O2 157.82(12) . 3_656 ?
O4 Zn1 Zn1 83.26(8) 2_645 3_656 ?
N1 Zn1 Zn1 167.96(9) . 3_656 ?
O3 Zn1 Zn1 74.50(8) 4_566 3_656 ?
O1 Zn1 Zn1 86.30(8) . 3_656 ?
O2 Zn1 Zn1 71.58(8) 3_656 3_656 ?
C1 N1 C5 116.6(3) . . ?
C1 N1 Zn1 119.7(3) . . ?
C5 N1 Zn1 123.8(2) . . ?
C14 O1 Zn1 118.6(2) . . ?
C14 O2 Zn1 138.0(3) . 3_656 ?
C15 O3 Zn1 134.1(3) . 4_665 ?
C15 O4 Zn1 123.1(2) . 2_655 ?
N1 C1 C2 123.6(4) . . ?
C1 C2 C3 120.5(4) . . ?
C2 C3 C4 115.8(4) . . ?
C2 C3 C6 122.8(4) . . ?
C4 C3 C6 121.4(3) . . ?
C5 C4 C3 120.4(4) . . ?
N1 C5 C4 123.2(3) . . ?
C7 C6 C3 124.9(4) . . ?
C6 C7 C7 124.2(5) . 3_455 ?
C9 C8 C13 119.4(3) . . ?
C9 C8 C14 121.3(3) . . ?
C13 C8 C14 119.2(3) . . ?
C8 C9 C10 120.0(3) . . ?
C11 C10 C9 120.6(3) . . ?
C12 C11 C10 119.1(3) . . ?
C12 C11 C15 120.9(3) . . ?
C10 C11 C15 120.0(3) . . ?
C13 C12 C11 120.1(3) . . ?
C12 C13 C8 120.8(3) . . ?
O2 C14 O1 125.1(3) . . ?
O2 C14 C8 117.0(3) . . ?
O1 C14 C8 117.9(3) . . ?
O4 C15 O3 124.9(3) . . ?
O4 C15 C11 117.7(3) . . ?
O3 C15 C11 117.3(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H2W O1 0.85 2.50 3.075(7) 126.0 .
O5 H1W O2 0.85 2.49 3.325(7) 167.1 4_565

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.769
_refine_diff_density_rms         0.089
####################################################################### 
# 
# 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 1038880'
_audit_update_record             
;
2015-05-06 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

#==========================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H18 N2 O4 Zn'
_chemical_formula_sum            'C24 H18 N2 O4 Zn'
_chemical_formula_weight         463.78

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'F d d d'
_symmetry_space_group_name_Hall  '-F 2uv 2vw'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+3/4, -y+3/4, z'
'-x+3/4, y, -z+3/4'
'x, -y+3/4, -z+3/4'
'x, y+1/2, z+1/2'
'-x+3/4, -y+5/4, z+1/2'
'-x+3/4, y+1/2, -z+5/4'
'x, -y+5/4, -z+5/4'
'x+1/2, y, z+1/2'
'-x+5/4, -y+3/4, z+1/2'
'-x+5/4, y, -z+5/4'
'x+1/2, -y+3/4, -z+5/4'
'x+1/2, y+1/2, z'
'-x+5/4, -y+5/4, z'
'-x+5/4, y+1/2, -z+3/4'
'x+1/2, -y+5/4, -z+3/4'
'-x, -y, -z'
'x-3/4, y-3/4, -z'
'x-3/4, -y, z-3/4'
'-x, y-3/4, z-3/4'
'-x, -y+1/2, -z+1/2'
'x-3/4, y-1/4, -z+1/2'
'x-3/4, -y+1/2, z-1/4'
'-x, y-1/4, z-1/4'
'-x+1/2, -y, -z+1/2'
'x-1/4, y-3/4, -z+1/2'
'x-1/4, -y, z-1/4'
'-x+1/2, y-3/4, z-1/4'
'-x+1/2, -y+1/2, -z'
'x-1/4, y-1/4, -z'
'x-1/4, -y+1/2, z-3/4'
'-x+1/2, y-1/4, z-3/4'

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.234 0.125 0.125 417 51 ' '
2 0.734 0.125 0.625 417 51 ' '
3 0.762 0.375 0.375 417 51 ' '
4 0.262 0.375 0.875 417 51 ' '
5 0.734 0.625 0.125 417 51 ' '
6 0.234 0.625 0.625 417 51 ' '
7 0.262 0.875 0.375 417 51 ' '
8 0.762 0.875 0.875 417 51 ' '
_platon_squeeze_details          
;
;

_cell_length_a                   14.093(3)
_cell_length_b                   26.670(5)
_cell_length_c                   28.668(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     10775(4)
_cell_formula_units_Z            16
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3776
_exptl_absorpt_coefficient_mu    0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8644
_exptl_absorpt_correction_T_max  0.8958
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_special_details           
; 
 ?  
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7347
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.45
_diffrn_reflns_theta_max         25.05
_reflns_number_total             2376
_reflns_number_gt                1778
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    Diamond
_computing_publication_material  'SHELXTL and PLATON (Spek, 2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1330P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2376
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0656
_refine_ls_wR_factor_ref         0.2016
_refine_ls_wR_factor_gt          0.1884
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.3750 0.3750 0.58478(2) 0.0366(3) Uani 1 2 d S . .
N1 N 0.4557(2) 0.41745(13) 0.62916(12) 0.0419(9) Uani 1 1 d . . .
O1 O 0.4648(3) 0.3460(2) 0.5415(2) 0.125(3) Uani 1 1 d . . .
O2 O 0.4995(3) 0.2951(2) 0.5955(3) 0.127(2) Uani 1 1 d . . .
C1 C 0.5141(4) 0.3952(2) 0.6587(2) 0.0636(15) Uani 1 1 d . . .
H1 H 0.5142 0.3599 0.6598 0.076 Uiso 1 1 calc R . .
C2 C 0.5743(3) 0.42058(18) 0.6876(2) 0.0645(15) Uani 1 1 d . . .
H2 H 0.6143 0.4029 0.7080 0.077 Uiso 1 1 calc R . .
C3 C 0.5761(3) 0.47189(17) 0.68664(16) 0.0457(11) Uani 1 1 d . . .
C4 C 0.5149(3) 0.49539(17) 0.65640(17) 0.0531(12) Uani 1 1 d . . .
H4 H 0.5140 0.5306 0.6546 0.064 Uiso 1 1 calc R . .
C5 C 0.4550(3) 0.46765(16) 0.62876(16) 0.0460(11) Uani 1 1 d . . .
H5 H 0.4122 0.4844 0.6090 0.055 Uiso 1 1 calc R . .
C6 C 0.6421(3) 0.50248(19) 0.71435(17) 0.0528(12) Uani 1 1 d . . .
H6 H 0.6310 0.5372 0.7160 0.063 Uiso 1 1 calc R . .
C7 C 0.7179(3) 0.48392(19) 0.73770(15) 0.0522(12) Uani 1 1 d . . .
H7 H 0.7287 0.4491 0.7378 0.063 Uiso 1 1 calc R . .
C8 C 0.5145(4) 0.3164(4) 0.5515(5) 0.142(5) Uani 1 1 d . . .
C9 C 0.5960(3) 0.2942(2) 0.5277(3) 0.077(2) Uani 1 1 d . . .
C10 C 0.6589(5) 0.2652(3) 0.5472(4) 0.120(3) Uani 1 1 d . . .
H10 H 0.6518 0.2577 0.5790 0.144 Uiso 1 1 calc R . .
C11 C 0.6251(8) 0.2994(4) 0.4883(5) 0.069(3) Uani 0.50 1 d P . .
H11 H 0.5880 0.3211 0.4700 0.083 Uiso 0.50 1 calc PR . .
C12 C 0.6966(10) 0.2812(6) 0.4669(5) 0.086(4) Uani 0.50 1 d P . .
H12 H 0.7003 0.2893 0.4351 0.103 Uiso 0.50 1 calc PR . .
C13 C 0.7531(9) 0.2580(4) 0.4797(7) 0.170(10) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 1.935(4) 2 ?
Zn1 O1 1.935(4) . ?
Zn1 N1 2.048(3) 2 ?
Zn1 N1 2.048(3) . ?
N1 C1 1.321(6) . ?
N1 C5 1.339(5) . ?
O1 C8 1.093(12) . ?
O2 C8 1.399(15) . ?
C1 C2 1.366(7) . ?
C1 H1 0.9400 . ?
C2 C3 1.369(6) . ?
C2 H2 0.9400 . ?
C3 C4 1.374(6) . ?
C3 C6 1.471(6) . ?
C4 C5 1.374(6) . ?
C4 H4 0.9400 . ?
C5 H5 0.9400 . ?
C6 C7 1.354(6) . ?
C6 H6 0.9400 . ?
C7 C7 1.432(8) 25_666 ?
C7 H7 0.9400 . ?
C8 C9 1.461(8) . ?
C9 C11 1.208(14) . ?
C9 C10 1.302(11) . ?
C10 C13 1.587(19) 29_656 ?
C10 C11 1.977(17) . ?
C10 H10 0.9400 . ?
C11 C12 1.276(17) . ?
C11 H11 0.9400 . ?
C12 C13 1.073(17) . ?
C12 C13 1.984(19) 29_656 ?
C12 H12 0.9400 . ?
C13 C13 1.24(3) 29_656 ?
C13 C10 1.587(19) 29_656 ?
C13 C12 1.984(19) 29_656 ?

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 O1 100.2(4) 2 . ?
O1 Zn1 N1 104.87(15) 2 2 ?
O1 Zn1 N1 122.7(2) . 2 ?
O1 Zn1 N1 122.7(2) 2 . ?
O1 Zn1 N1 104.87(15) . . ?
N1 Zn1 N1 103.2(2) 2 . ?
C1 N1 C5 117.4(4) . . ?
C1 N1 Zn1 119.7(3) . . ?
C5 N1 Zn1 122.9(3) . . ?
C8 O1 Zn1 122.6(9) . . ?
N1 C1 C2 123.5(5) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C1 C2 C3 119.7(4) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 117.2(4) . . ?
C2 C3 C6 123.8(4) . . ?
C4 C3 C6 119.0(4) . . ?
C5 C4 C3 120.3(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
N1 C5 C4 121.9(4) . . ?
N1 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C7 C6 C3 124.3(4) . . ?
C7 C6 H6 117.9 . . ?
C3 C6 H6 117.9 . . ?
C6 C7 C7 121.5(6) . 25_666 ?
C6 C7 H7 119.2 . . ?
C7 C7 H7 119.2 25_666 . ?
O1 C8 O2 115.6(7) . . ?
O1 C8 C9 132.3(14) . . ?
O2 C8 C9 112.1(11) . . ?
C11 C9 C10 103.8(7) . . ?
C11 C9 C8 131.0(11) . . ?
C10 C9 C8 125.0(10) . . ?
C9 C10 C13 123.7(10) . 29_656 ?
C13 C10 C11 87.3(8) 29_656 . ?
C9 C10 H10 118.2 . . ?
C13 C10 H10 118.2 29_656 . ?
C11 C10 H10 154.5 . . ?
C9 C11 C12 132.3(13) . . ?
C12 C11 C10 92.6(9) . . ?
C9 C11 H11 113.8 . . ?
C12 C11 H11 113.8 . . ?
C10 C11 H11 153.5 . . ?
C13 C12 C11 129.8(18) . . ?
C11 C12 C13 96.4(11) . 29_656 ?
C13 C12 H12 115.1 . . ?
C11 C12 H12 115.1 . . ?
C13 C12 H12 148.3 29_656 . ?
C12 C13 C13 118(2) . 29_656 ?
C12 C13 C10 129.7(19) . 29_656 ?
C13 C13 C10 112.1(12) 29_656 29_656 ?
C12 C13 C12 146.4(17) . 29_656 ?
C10 C13 C12 83.7(7) 29_656 29_656 ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.421
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.098

#===END
####################################################################### 
# 
# 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 1038881'
_audit_update_record             
;
2014-12-11 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

#==========================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H18 N2 O4 Zn, 2(H2 O)'
_chemical_formula_sum            'C23 H22 N2 O6 Zn'
_chemical_formula_weight         487.82

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P b c m'
_symmetry_space_group_name_Hall  '-P 2c 2b'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y-1/2, z'

_cell_length_a                   5.8174(12)
_cell_length_b                   23.023(5)
_cell_length_c                   20.386(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2730.4(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_absorpt_coefficient_mu    0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8070
_exptl_absorpt_correction_T_max  0.8353
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_special_details           
; 
 ?  
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9805
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.48
_diffrn_reflns_theta_max         25.05
_reflns_number_total             2449
_reflns_number_gt                1924
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    Diamond
_computing_publication_material  'SHELXTL and PLATON (Spek, 2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0669P)²+8.7288P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2449
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0722
_refine_ls_wR_factor_ref         0.1865
_refine_ls_wR_factor_gt          0.1749
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_restrained_S_all      1.166
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 1.42662(15) 0.2500 1.0000 0.0302(3) Uani 1 2 d S . .
N1 N 1.2104(8) 0.31913(17) 0.98923(19) 0.0327(10) Uani 1 1 d . . .
O1 O 1.6279(6) 0.26182(16) 0.92357(16) 0.0388(9) Uani 1 1 d . . .
O2 O 1.3962(13) 0.2040(4) 0.8720(2) 0.151(4) Uani 1 1 d . . .
C1 C 1.2446(10) 0.3606(2) 0.9441(2) 0.0368(12) Uani 1 1 d . . .
H1 H 1.3741 0.3578 0.9167 0.044 Uiso 1 1 calc R . .
C2 C 1.0995(11) 0.4070(2) 0.9360(3) 0.0444(14) Uani 1 1 d . . .
H2 H 1.1295 0.4348 0.9034 0.053 Uiso 1 1 calc R . .
C3 C 0.9086(10) 0.4128(2) 0.9760(3) 0.0393(13) Uani 1 1 d . . .
C4 C 0.8734(11) 0.3701(3) 1.0222(3) 0.0473(15) Uani 1 1 d . . .
H4 H 0.7450 0.3720 1.0501 0.057 Uiso 1 1 calc R . .
C5 C 1.0266(9) 0.3245(2) 1.0275(3) 0.0409(13) Uani 1 1 d . . .
H5 H 0.9996 0.2960 1.0596 0.049 Uiso 1 1 calc R . .
C6 C 0.7557(11) 0.4634(2) 0.9689(4) 0.0537(16) Uani 1 1 d . . .
H6 H 0.7911 0.4900 0.9354 0.064 Uiso 1 1 calc R . .
C7 C 0.5721(11) 0.4748(3) 1.0055(3) 0.0521(16) Uani 1 1 d . . .
H7 H 0.5345 0.4493 1.0399 0.062 Uiso 1 1 calc R . .
C8 C 1.5688(17) 0.2369(4) 0.7500 0.050(2) Uani 1 2 d S . .
H8 H 1.4441 0.2109 0.7500 0.060 Uiso 1 2 calc SR . .
C9 C 1.6606(11) 0.2560(2) 0.8090(2) 0.0420(13) Uani 1 1 d . . .
C10 C 1.8500(10) 0.2927(2) 0.8085(2) 0.0422(14) Uani 1 1 d . . .
H10 H 1.9147 0.3049 0.8485 0.051 Uiso 1 1 calc R . .
C11 C 1.9451(15) 0.3118(4) 0.7500 0.046(2) Uani 1 2 d S . .
C12 C 2.1485(19) 0.3536(4) 0.7500 0.066(3) Uani 1 2 d S . .
H12A H 2.1987 0.3603 0.7053 0.099 Uiso 0.50 1 calc PR . .
H12B H 2.2737 0.3369 0.7751 0.099 Uiso 0.50 1 calc PR . .
H12C H 2.1024 0.3902 0.7696 0.099 Uiso 0.50 1 calc PR . .
C13 C 1.5513(11) 0.2385(3) 0.8724(3) 0.0528(17) Uani 1 1 d . . .
O3 O 0.888(3) 0.0304(5) 0.6743(6) 0.125(6) Uani 0.50 1 d P . .
H1W H 0.9282 0.0642 0.6865 0.187 Uiso 0.50 1 d PR . .
H2W H 0.9960 0.0123 0.6935 0.187 Uiso 0.50 1 d PR . .
O4 O 1.363(5) 0.0927(6) 0.8213(7) 0.245(16) Uani 0.50 1 d P . .
H3W H 1.5043 0.0831 0.8208 0.368 Uiso 0.50 1 d PR . .
H4W H 1.3315 0.0981 0.8615 0.368 Uiso 0.50 1 d PR . .


_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 1.968(4) 4_557 ?
Zn1 O1 1.968(4) . ?
Zn1 N1 2.041(4) . ?
Zn1 N1 2.041(4) 4_557 ?
N1 C5 1.329(7) . ?
N1 C1 1.341(6) . ?
O1 C13 1.254(7) . ?
O2 C13 1.203(8) . ?
C1 C2 1.370(8) . ?
C1 H1 0.9400 . ?
C2 C3 1.384(8) . ?
C2 H2 0.9400 . ?
C3 C4 1.376(8) . ?
C3 C6 1.473(8) . ?
C4 C5 1.381(8) . ?
C4 H4 0.9400 . ?
C5 H5 0.9400 . ?
C6 C7 1.330(9) . ?
C6 H6 0.9400 . ?
C7 C7 1.449(12) 5_667 ?
C7 H7 0.9400 . ?
C8 C9 1.388(7) . ?
C8 C9 1.388(7) 6_557 ?
C8 H8 0.9400 . ?
C9 C10 1.390(8) . ?
C9 C13 1.496(8) . ?
C10 C11 1.387(7) . ?
C10 H10 0.9400 . ?
C11 C10 1.387(7) 6_557 ?
C11 C12 1.525(12) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
O3 H1W 0.8501 . ?
O3 H2W 0.8499 . ?
O4 H3W 0.8500 . ?
O4 H4W 0.8501 . ?

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 O1 107.0(2) 4_557 . ?
O1 Zn1 N1 124.04(15) 4_557 . ?
O1 Zn1 N1 100.01(16) . . ?
O1 Zn1 N1 100.00(16) 4_557 4_557 ?
O1 Zn1 N1 124.04(15) . 4_557 ?
N1 Zn1 N1 103.9(2) . 4_557 ?
C5 N1 C1 117.1(5) . . ?
C5 N1 Zn1 120.4(3) . . ?
C1 N1 Zn1 122.5(4) . . ?
C13 O1 Zn1 112.8(4) . . ?
N1 C1 C2 123.0(5) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C1 C2 C3 119.9(5) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 117.0(5) . . ?
C4 C3 C6 122.9(6) . . ?
C2 C3 C6 120.2(6) . . ?
C3 C4 C5 120.0(6) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
N1 C5 C4 123.0(5) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
C7 C6 C3 125.9(6) . . ?
C7 C6 H6 117.0 . . ?
C3 C6 H6 117.0 . . ?
C6 C7 C7 122.4(8) . 5_667 ?
C6 C7 H7 118.8 . . ?
C7 C7 H7 118.8 5_667 . ?
C9 C8 C9 120.2(8) . 6_557 ?
C9 C8 H8 119.9 . . ?
C9 C8 H8 119.9 6_557 . ?
C8 C9 C10 119.5(5) . . ?
C8 C9 C13 120.0(6) . . ?
C10 C9 C13 120.4(5) . . ?
C11 C10 C9 121.0(5) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C10 118.8(7) . 6_557 ?
C10 C11 C12 120.6(4) . . ?
C10 C11 C12 120.6(4) 6_557 . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 O1 123.7(6) . . ?
O2 C13 C9 119.4(6) . . ?
O1 C13 C9 116.9(5) . . ?
H1W O3 H2W 96.3 . . ?
H3W O4 H4W 105.0 . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.836
_refine_diff_density_min         -0.876
_refine_diff_density_rms         0.094
####################################################################### 
# 
# 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 1038882'
_audit_update_record             
;
2014-12-11 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

#==========================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C15 H11 N2 O4 Zn), 3(H2 O)'
_chemical_formula_sum            'C30 H28 N4 O11 Zn2'
_chemical_formula_weight         751.34

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

loop_
_symmetry_equiv_pos_as_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                   29.425(6)
_cell_length_b                   7.7142(15)
_cell_length_c                   16.062(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.04(3)
_cell_angle_gamma                90.00
_cell_volume                     3504.1(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1536
_exptl_absorpt_coefficient_mu    1.429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6347
_exptl_absorpt_correction_T_max  0.7076
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_special_details           
; 
 ?   
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7896
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         25.05
_reflns_number_total             3086
_reflns_number_gt                2364
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    Diamond
_computing_publication_material  'SHELXTL and PLATON (Spek, 2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1029P)²+11.3594P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3086
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1836
_refine_ls_wR_factor_gt          0.1672
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.67550(2) 0.74819(6) 0.69098(3) 0.0280(3) Uani 1 1 d . . .
N1 N 0.61892(15) 0.6029(5) 0.6272(3) 0.0335(9) Uani 1 1 d . . .
N2 N 0.73393(14) 0.6291(5) 0.6648(2) 0.0269(9) Uani 1 1 d . . .
H2A H 0.7355 0.6112 0.7190 0.032 Uiso 1 1 calc R . .
H2B H 0.7411 0.7303 0.6481 0.032 Uiso 1 1 calc R . .
O1 O 0.68719(12) -0.0003(4) 0.68237(19) 0.0290(7) Uani 1 1 d . . .
O2 O 0.66955(14) -0.0959(4) 0.5487(2) 0.0390(9) Uani 1 1 d . . .
O3 O 0.70474(13) 0.5565(4) 0.3359(2) 0.0357(8) Uani 1 1 d . . .
O4 O 0.67862(13) 0.2852(4) 0.3127(2) 0.0325(8) Uani 1 1 d . . .
C1 C 0.5979(2) 0.6141(8) 0.5432(4) 0.0608(19) Uani 1 1 d . . .
H1 H 0.6043 0.7108 0.5127 0.073 Uiso 1 1 calc R . .
C2 C 0.5671(3) 0.4907(11) 0.4987(5) 0.087(3) Uani 1 1 d . . .
H2 H 0.5532 0.5046 0.4389 0.105 Uiso 1 1 calc R . .
C3 C 0.5562(2) 0.3478(9) 0.5396(4) 0.0557(17) Uani 1 1 d . . .
C4 C 0.5784(3) 0.3354(9) 0.6270(4) 0.068(2) Uani 1 1 d . . .
H4 H 0.5730 0.2386 0.6585 0.081 Uiso 1 1 calc R . .
C5 C 0.6082(2) 0.4630(9) 0.6675(4) 0.0599(18) Uani 1 1 d . . .
H5 H 0.6221 0.4526 0.7275 0.072 Uiso 1 1 calc R . .
C6 C 0.5249(3) 0.2143(11) 0.4921(5) 0.076(2) Uani 1 1 d . . .
H6 H 0.5097 0.2363 0.4334 0.091 Uiso 1 1 calc R . .
C7 C 0.5158(3) 0.0652(10) 0.5239(5) 0.072(2) Uani 1 1 d . . .
H7 H 0.5312 0.0420 0.5824 0.087 Uiso 1 1 calc R . .
C8 C 0.71955(15) 0.4912(6) 0.6027(3) 0.0218(9) Uani 1 1 d . . .
C9 C 0.70836(16) 0.3320(6) 0.6305(3) 0.0234(10) Uani 1 1 d . . .
H9 H 0.7117 0.3138 0.6897 0.028 Uiso 1 1 calc R . .
C10 C 0.69237(16) 0.1991(6) 0.5724(3) 0.0224(9) Uani 1 1 d . . .
C11 C 0.68728(16) 0.2279(5) 0.4837(3) 0.0223(10) Uani 1 1 d . . .
H11 H 0.6764 0.1384 0.4434 0.027 Uiso 1 1 calc R . .
C12 C 0.69829(16) 0.3876(6) 0.4563(3) 0.0239(10) Uani 1 1 d . . .
C13 C 0.71431(15) 0.5198(6) 0.5151(3) 0.0236(9) Uani 1 1 d . . .
H13 H 0.7216 0.6287 0.4959 0.028 Uiso 1 1 calc R . .
C14 C 0.68208(15) 0.0236(6) 0.6015(3) 0.0241(10) Uani 1 1 d . . .
C15 C 0.69370(16) 0.4157(6) 0.3613(3) 0.0245(10) Uani 1 1 d . . .
O5 O 0.6381(3) 0.8194(11) 0.3667(5) 0.128(3) Uani 1 1 d . . .
H1W H 0.6114 0.8589 0.3380 0.192 Uiso 1 1 d R . .
H2W H 0.6646 0.8661 0.3692 0.192 Uiso 1 1 d R . .
O6 O 0.5973(10) 0.073(3) 0.2507(19) 0.276(19) Uani 0.50 1 d P . .
H3W H 0.5731 0.0857 0.2692 0.415 Uiso 0.50 1 d PR . .
H4W H 0.6077 0.0807 0.2064 0.415 Uiso 0.50 1 d PR . .


_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 O4 1.950(3) 6_566 ?
Zn1 O1 1.982(3) 1_565 ?
Zn1 N1 2.033(4) . ?
Zn1 N2 2.092(4) . ?
N1 C1 1.323(7) . ?
N1 C5 1.341(7) . ?
N2 C8 1.440(5) . ?
N2 H2A 0.8700 . ?
N2 H2B 0.8700 . ?
O1 C14 1.279(5) . ?
O1 Zn1 1.982(3) 1_545 ?
O2 C14 1.238(5) . ?
O3 C15 1.234(5) . ?
O4 C15 1.276(6) . ?
O4 Zn1 1.950(3) 6_565 ?
C1 C2 1.371(8) . ?
C1 H1 0.9400 . ?
C2 C3 1.366(9) . ?
C2 H2 0.9400 . ?
C3 C4 1.378(9) . ?
C3 C6 1.450(9) . ?
C4 C5 1.358(8) . ?
C4 H4 0.9400 . ?
C5 H5 0.9400 . ?
C6 C7 1.315(10) . ?
C6 H6 0.9400 . ?
C7 C7 1.441(12) 5_656 ?
C7 H7 0.9400 . ?
C8 C9 1.377(6) . ?
C8 C13 1.390(6) . ?
C9 C10 1.378(6) . ?
C9 H9 0.9400 . ?
C10 C11 1.409(6) . ?
C10 C14 1.490(6) . ?
C11 C12 1.377(6) . ?
C11 H11 0.9400 . ?
C12 C13 1.381(6) . ?
C12 C15 1.510(6) . ?
C13 H13 0.9400 . ?
O5 H1W 0.8502 . ?
O5 H2W 0.8498 . ?
O6 H3W 0.8499 . ?
O6 H4W 0.8500 . ?

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
O4 Zn1 O1 103.79(13) 6_566 1_565 ?
O4 Zn1 N1 103.73(16) 6_566 . ?
O1 Zn1 N1 129.66(16) 1_565 . ?
O4 Zn1 N2 109.28(15) 6_566 . ?
O1 Zn1 N2 104.34(14) 1_565 . ?
N1 Zn1 N2 105.12(15) . . ?
C1 N1 C5 116.0(5) . . ?
C1 N1 Zn1 124.4(4) . . ?
C5 N1 Zn1 118.1(4) . . ?
C8 N2 Zn1 111.3(3) . . ?
C8 N2 H2A 120.0 . . ?
Zn1 N2 H2A 71.7 . . ?
C8 N2 H2B 120.0 . . ?
Zn1 N2 H2B 87.2 . . ?
H2A N2 H2B 120.0 . . ?
C14 O1 Zn1 103.8(3) . 1_545 ?
C15 O4 Zn1 129.0(3) . 6_565 ?
N1 C1 C2 122.8(6) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C3 C2 C1 121.2(6) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 115.9(6) . . ?
C2 C3 C6 121.2(6) . . ?
C4 C3 C6 122.8(6) . . ?
C5 C4 C3 120.0(6) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
N1 C5 C4 124.0(6) . . ?
N1 C5 H5 118.0 . . ?
C4 C5 H5 118.0 . . ?
C7 C6 C3 125.7(7) . . ?
C7 C6 H6 117.2 . . ?
C3 C6 H6 117.2 . . ?
C6 C7 C7 125.0(9) . 5_656 ?
C6 C7 H7 117.5 . . ?
C7 C7 H7 117.5 5_656 . ?
C9 C8 C13 120.0(4) . . ?
C9 C8 N2 119.0(4) . . ?
C13 C8 N2 120.9(4) . . ?
C8 C9 C10 120.8(4) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C11 119.2(4) . . ?
C9 C10 C14 121.7(4) . . ?
C11 C10 C14 119.1(4) . . ?
C12 C11 C10 119.7(4) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.5(4) . . ?
C11 C12 C15 119.2(4) . . ?
C13 C12 C15 120.2(4) . . ?
C12 C13 C8 119.8(4) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
O2 C14 O1 121.1(4) . . ?
O2 C14 C10 120.7(4) . . ?
O1 C14 C10 118.2(4) . . ?
O3 C15 O4 124.8(4) . . ?
O3 C15 C12 120.1(4) . . ?
O4 C15 C12 115.0(4) . . ?
H1W O5 H2W 124.9 . . ?
H3W O6 H4W 144.6 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.026
_refine_diff_density_min         -0.677
_refine_diff_density_rms         0.122
####################################################################### 
# 
# 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 1038883'
_audit_update_record             
;
2014-12-11 deposited with the CCDC.
2015-05-07 downloaded from the CCDC.
;

#==========================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H16 N2 O8 Zn'
_chemical_formula_sum            'C24 H16 N2 O8 Zn'
_chemical_formula_weight         525.78

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.0776(18)
_cell_length_b                   13.726(3)
_cell_length_c                   18.827(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.96(3)
_cell_angle_gamma                90.00
_cell_volume                     2190.6(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    1.177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7191
_exptl_absorpt_correction_T_max  0.7735
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_special_details           
; 
 ?  
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10908
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         25.04
_reflns_number_total             3877
_reflns_number_gt                3214
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    Diamond
_computing_publication_material  'SHELXTL and PLATON (Spek, 2009)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0328P)²+0.4131P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3877
_refine_ls_number_parameters     324
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0727
_refine_ls_wR_factor_gt          0.0673
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.59167(3) 0.856312(18) 0.630292(14) 0.01701(10) Uani 1 1 d . . .
N1 N 0.7077(2) 0.86206(13) 0.74494(10) 0.0210(4) Uani 1 1 d . . .
N2 N 1.2911(3) 0.85935(16) 1.40497(14) 0.0431(7) Uani 1 1 d . . .
O1 O 0.57269(19) 0.71718(11) 0.61423(9) 0.0269(4) Uani 1 1 d . . .
O2 O 0.3225(2) 0.72736(12) 0.53454(11) 0.0392(5) Uani 1 1 d . . .
O3 O 0.4691(3) 0.55174(13) 0.68481(10) 0.0441(5) Uani 1 1 d . . .
O4 O 0.6795(2) 0.45680(16) 0.70379(11) 0.0444(5) Uani 1 1 d . . .
O5 O 0.76206(18) 0.91072(12) 0.60212(8) 0.0245(4) Uani 1 1 d . . .
O6 O 0.64429(18) 0.85540(11) 0.48362(9) 0.0243(4) Uani 1 1 d . . .
O7 O 0.65433(19) 1.07966(14) 0.33725(9) 0.0356(5) Uani 1 1 d . . .
O8 O 0.58409(17) 1.06369(11) 0.43646(8) 0.0218(4) Uani 1 1 d . . .
C1 C 0.8509(3) 0.90211(17) 0.77478(13) 0.0255(5) Uani 1 1 d . . .
H1 H 0.8949 0.9313 0.7418 0.031 Uiso 1 1 calc R . .
C2 C 0.9367(3) 0.90257(18) 0.85140(14) 0.0291(6) Uani 1 1 d . . .
H2 H 1.0373 0.9313 0.8697 0.035 Uiso 1 1 calc R . .
C3 C 0.8750(3) 0.86071(17) 0.90177(13) 0.0266(6) Uani 1 1 d . . .
C4 C 0.7268(3) 0.81727(19) 0.87058(13) 0.0292(6) Uani 1 1 d . . .
H4 H 0.6812 0.7862 0.9022 0.035 Uiso 1 1 calc R . .
C5 C 0.6484(3) 0.82027(18) 0.79342(13) 0.0267(6) Uani 1 1 d . . .
H5 H 0.5479 0.7916 0.7734 0.032 Uiso 1 1 calc R . .
C6 C 0.9676(3) 0.86074(19) 0.98297(14) 0.0328(6) Uani 1 1 d . . .
H6 H 1.0747 0.8774 0.9968 0.039 Uiso 1 1 calc R . .
C7 C 0.9183(3) 0.84000(18) 1.03997(14) 0.0319(6) Uani 1 1 d . . .
H7 H 0.8126 0.8221 1.0292 0.038 Uiso 1 1 calc R . .
C8 C 1.0249(3) 0.84462(18) 1.11783(14) 0.0319(6) Uani 1 1 d . . .
H8 H 1.1318 0.8572 1.1266 0.038 Uiso 1 1 calc R . .
C9 C 0.9837(3) 0.83247(19) 1.17847(14) 0.0331(6) Uani 1 1 d . . .
H9 H 0.8779 0.8174 1.1703 0.040 Uiso 1 1 calc R . .
C10 C 1.0932(3) 0.84113(17) 1.25649(14) 0.0279(6) Uani 1 1 d . . .
C11 C 1.0382(3) 0.83261(19) 1.31684(14) 0.0353(6) Uani 1 1 d . . .
H11 H 0.9305 0.8212 1.3068 0.042 Uiso 1 1 calc R . .
C12 C 1.1400(4) 0.84084(19) 1.39010(15) 0.0421(8) Uani 1 1 d . . .
H12 H 1.1026 0.8333 1.4303 0.050 Uiso 1 1 calc R . .
C13 C 1.3491(3) 0.86959(19) 1.34981(16) 0.0403(7) Uani 1 1 d . . .
H13 H 1.4568 0.8835 1.3622 0.048 Uiso 1 1 calc R . .
C14 C 1.2541(3) 0.86014(19) 1.27566(15) 0.0352(7) Uani 1 1 d . . .
H14 H 1.2967 0.8664 1.2372 0.042 Uiso 1 1 calc R . .
C15 C 0.4352(3) 0.57837(16) 0.45399(13) 0.0257(6) Uani 1 1 d . . .
H15 H 0.3909 0.6320 0.4226 0.031 Uiso 1 1 calc R . .
C16 C 0.4702(3) 0.58614(16) 0.53192(13) 0.0233(5) Uani 1 1 d . . .
C17 C 0.5358(3) 0.50642(16) 0.57843(13) 0.0246(5) Uani 1 1 d . . .
C18 C 0.5569(3) 0.50960(17) 0.66098(14) 0.0287(6) Uani 1 1 d . . .
C19 C 0.4486(3) 0.68469(17) 0.56292(13) 0.0247(6) Uani 1 1 d . . .
C20 C 1.0283(3) 0.93756(16) 0.56045(12) 0.0188(5) Uani 1 1 d . . .
H20 H 1.0478 0.8953 0.6021 0.023 Uiso 1 1 calc R . .
C21 C 0.8735(3) 0.95526(16) 0.51327(12) 0.0175(5) Uani 1 1 d . . .
C22 C 0.8455(3) 1.01957(16) 0.45223(12) 0.0178(5) Uani 1 1 d . . .
C23 C 0.6835(3) 1.05446(16) 0.40404(12) 0.0194(5) Uani 1 1 d . . .
C24 C 0.7465(2) 0.90284(16) 0.53202(12) 0.0179(5) Uani 1 1 d . . .
H1A H 0.677(4) 0.455(2) 0.7461(19) 0.061(11) Uiso 1 1 d . . .
H2A H 1.354(4) 0.867(3) 1.449(2) 0.075(12) 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 1.9315(15) . ?
Zn1 O5 1.9540(16) . ?
Zn1 O8 1.9738(16) 3_676 ?
Zn1 N1 2.037(2) . ?
N1 C1 1.336(3) . ?
N1 C5 1.343(3) . ?
N2 C12 1.323(4) . ?
N2 C13 1.329(4) . ?
N2 H2A 0.83(4) . ?
O1 C19 1.274(3) . ?
O2 C19 1.225(3) . ?
O3 C18 1.195(3) . ?
O4 C18 1.331(3) . ?
O4 H1A 0.81(3) . ?
O5 C24 1.281(3) . ?
O6 C24 1.229(3) . ?
O7 C23 1.238(3) . ?
O8 C23 1.264(3) . ?
O8 Zn1 1.9738(16) 3_676 ?
C1 C2 1.372(3) . ?
C1 H1 0.9400 . ?
C2 C3 1.386(4) . ?
C2 H2 0.9400 . ?
C3 C4 1.395(4) . ?
C3 C6 1.457(3) . ?
C4 C5 1.371(3) . ?
C4 H4 0.9400 . ?
C5 H5 0.9400 . ?
C6 C7 1.333(4) . ?
C6 H6 0.9400 . ?
C7 C8 1.440(3) . ?
C7 H7 0.9400 . ?
C8 C9 1.333(4) . ?
C8 H8 0.9400 . ?
C9 C10 1.454(3) . ?
C9 H9 0.9400 . ?
C10 C14 1.398(4) . ?
C10 C11 1.400(4) . ?
C11 C12 1.363(4) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C14 1.359(4) . ?
C13 H13 0.9400 . ?
C14 H14 0.9400 . ?
C15 C17 1.382(3) 3_666 ?
C15 C16 1.390(3) . ?
C15 H15 0.9400 . ?
C16 C17 1.395(3) . ?
C16 C19 1.513(3) . ?
C17 C15 1.382(3) 3_666 ?
C17 C18 1.497(3) . ?
C20 C22 1.382(3) 3_776 ?
C20 C21 1.389(3) . ?
C20 H20 0.9400 . ?
C21 C22 1.398(3) . ?
C21 C24 1.504(3) . ?
C22 C20 1.382(3) 3_776 ?
C22 C23 1.504(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O5 111.74(7) . . ?
O1 Zn1 O8 116.35(7) . 3_676 ?
O5 Zn1 O8 98.78(7) . 3_676 ?
O1 Zn1 N1 100.81(7) . . ?
O5 Zn1 N1 96.51(7) . . ?
O8 Zn1 N1 130.32(7) 3_676 . ?
C1 N1 C5 117.2(2) . . ?
C1 N1 Zn1 121.21(16) . . ?
C5 N1 Zn1 121.50(16) . . ?
C12 N2 C13 121.7(3) . . ?
C12 N2 H2A 122(3) . . ?
C13 N2 H2A 117(3) . . ?
C19 O1 Zn1 118.03(15) . . ?
C18 O4 H1A 108(2) . . ?
C24 O5 Zn1 116.18(14) . . ?
C23 O8 Zn1 107.61(14) . 3_676 ?
N1 C1 C2 123.0(2) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C1 C2 C3 120.1(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 117.0(2) . . ?
C2 C3 C6 119.7(2) . . ?
C4 C3 C6 123.3(2) . . ?
C5 C4 C3 119.4(2) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N1 C5 C4 123.4(2) . . ?
N1 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
C7 C6 C3 127.7(3) . . ?
C7 C6 H6 116.2 . . ?
C3 C6 H6 116.2 . . ?
C6 C7 C8 120.9(3) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 125.0(3) . . ?
C9 C8 H8 117.5 . . ?
C7 C8 H8 117.5 . . ?
C8 C9 C10 123.7(3) . . ?
C8 C9 H9 118.1 . . ?
C10 C9 H9 118.1 . . ?
C14 C10 C11 116.7(2) . . ?
C14 C10 C9 123.3(2) . . ?
C11 C10 C9 120.0(2) . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
N2 C12 C11 120.4(3) . . ?
N2 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
N2 C13 C14 120.6(3) . . ?
N2 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C10 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C10 C14 H14 119.9 . . ?
C17 C15 C16 121.5(2) 3_666 . ?
C17 C15 H15 119.2 3_666 . ?
C16 C15 H15 119.2 . . ?
C15 C16 C17 119.2(2) . . ?
C15 C16 C19 117.6(2) . . ?
C17 C16 C19 123.0(2) . . ?
C15 C17 C16 119.3(2) 3_666 . ?
C15 C17 C18 120.6(2) 3_666 . ?
C16 C17 C18 119.7(2) . . ?
O3 C18 O4 124.2(2) . . ?
O3 C18 C17 123.3(2) . . ?
O4 C18 C17 112.4(2) . . ?
O2 C19 O1 126.7(2) . . ?
O2 C19 C16 119.3(2) . . ?
O1 C19 C16 113.8(2) . . ?
C22 C20 C21 121.7(2) 3_776 . ?
C22 C20 H20 119.1 3_776 . ?
C21 C20 H20 119.1 . . ?
C20 C21 C22 118.7(2) . . ?
C20 C21 C24 116.83(19) . . ?
C22 C21 C24 124.4(2) . . ?
C20 C22 C21 119.5(2) 3_776 . ?
C20 C22 C23 116.88(19) 3_776 . ?
C21 C22 C23 123.2(2) . . ?
O7 C23 O8 122.2(2) . . ?
O7 C23 C22 120.6(2) . . ?
O8 C23 C22 116.99(19) . . ?
O6 C24 O5 125.8(2) . . ?
O6 C24 C21 121.2(2) . . ?
O5 C24 C21 112.96(19) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H1A O7 0.81(3) 1.86(3) 2.651(3) 167(3) 4_576

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.061
