# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_compound1
_database_code_depnum_ccdc_archive 'CCDC 1040066'
_audit_update_record             
;
2014-12-17 deposited with the CCDC.
2015-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H15 N O8 Zn, H2 O'
_chemical_formula_sum            'C11 H17 N O9 Zn'
_chemical_formula_weight         372.62

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

_cell_length_a                   12.3453(12)
_cell_length_b                   12.0038(12)
_cell_length_c                   20.971(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3107.7(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9940
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      26.37

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_F_000             1536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.624
_shelx_estimated_absorpt_T_min   0.600
_shelx_estimated_absorpt_T_max   0.759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.51
_exptl_absorpt_correction_T_max  0.71
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49680
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.549
_diffrn_reflns_theta_max         26.406
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3192
_reflns_number_gt                2665
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0665P)²+4.1639P] 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         3192
_refine_ls_number_parameters     224
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1186
_refine_ls_wR_factor_gt          0.1108
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.068
_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 0.19978(3) 1.15139(3) 0.71527(2) 0.02981(14) Uani 1 1 d . . . . .
O9 O 0.5779(2) 0.0343(3) 0.28679(12) 0.0557(7) Uani 1 1 d D . . . .
O1 O 0.24642(18) 1.05027(17) 0.64457(8) 0.0315(4) Uani 1 1 d . . . . .
O2 O 0.17391(19) 1.18725(19) 0.58839(10) 0.0385(5) Uani 1 1 d . . . . .
O3 O 0.3574(3) 1.27519(19) 0.38181(12) 0.0671(9) Uani 1 1 d . . . . .
O4 O 0.39370(18) 1.13172(18) 0.31948(9) 0.0365(5) Uani 1 1 d . . . . .
O5 O 0.5080(2) 0.79174(19) 0.38024(11) 0.0501(6) Uani 1 1 d . . . . .
O8 O 0.2901(2) 1.2899(2) 0.70346(14) 0.0550(7) Uani 1 1 d D . . . .
O7 O 0.0409(2) 1.1745(3) 0.73097(17) 0.0647(8) Uani 1 1 d D . . . .
O6 O 0.2547(2) 1.0677(2) 0.79267(12) 0.0504(6) Uani 1 1 d D . . . .
N1 N 0.42258(19) 0.80460(19) 0.47638(11) 0.0270(5) Uani 1 1 d . . . . .
H1N H 0.4078 0.7664 0.5100 0.041 Uiso 1 1 calc R U . . .
C1 C 0.2315(2) 1.1028(2) 0.59206(13) 0.0275(6) Uani 1 1 d . . . . .
C2 C 0.2896(2) 1.0602(2) 0.53413(12) 0.0255(6) Uani 1 1 d . . . . .
C3 C 0.3053(2) 1.1325(2) 0.48305(13) 0.0262(6) Uani 1 1 d . . . . .
H3 H 0.2799 1.2054 0.4854 0.031 Uiso 1 1 calc R U . . .
C4 C 0.3586(2) 1.0961(2) 0.42864(12) 0.0246(5) Uani 1 1 d . . . . .
C5 C 0.3707(2) 1.1750(2) 0.37292(14) 0.0323(6) Uani 1 1 d . . . . .
C6 C 0.3978(2) 0.9877(2) 0.42529(12) 0.0253(5) Uani 1 1 d . . . . .
H6 H 0.4332 0.9634 0.3887 0.030 Uiso 1 1 calc R U . . .
C7 C 0.3842(2) 0.9157(2) 0.47658(12) 0.0233(5) Uani 1 1 d . . . . .
C9 C 0.4790(2) 0.7502(2) 0.43106(14) 0.0322(6) Uani 1 1 d . . . . .
C10 C 0.5047(3) 0.6300(3) 0.44643(16) 0.0449(8) Uani 1 1 d . . . . .
H10A H 0.5824 0.6217 0.4515 0.054 Uiso 1 1 calc R U . . .
H10B H 0.4706 0.6100 0.4865 0.054 Uiso 1 1 calc R U . . .
C11 C 0.4662(4) 0.5524(3) 0.3952(2) 0.0651(12) Uani 1 1 d . . . . .
H11A H 0.3885 0.5553 0.3927 0.098 Uiso 1 1 calc R U . . .
H11B H 0.4887 0.4778 0.4050 0.098 Uiso 1 1 calc R U . . .
H11C H 0.4965 0.5746 0.3550 0.098 Uiso 1 1 calc R U . . .
C8 C 0.3298(2) 0.9523(2) 0.53098(12) 0.0259(6) Uani 1 1 d . . . . .
H8 H 0.3203 0.9042 0.5653 0.031 Uiso 1 1 calc R U . . .
H9A H 0.520(2) 0.065(3) 0.3015(16) 0.039 Uiso 1 1 d D U . . .
H9B H 0.615(3) 0.011(3) 0.3185(13) 0.039 Uiso 1 1 d D U . . .
H6B H 0.310(2) 1.027(3) 0.7813(17) 0.039 Uiso 1 1 d D U . . .
H6A H 0.277(3) 1.109(3) 0.8238(14) 0.039 Uiso 1 1 d D U . . .
H8A H 0.323(3) 1.319(3) 0.7359(13) 0.039 Uiso 1 1 d D U . . .
H8B H 0.343(2) 1.281(3) 0.6758(14) 0.039 Uiso 1 1 d D U . . .
H7B H 0.007(3) 1.206(3) 0.6998(13) 0.039 Uiso 1 1 d D U . . .
H7A H 0.008(3) 1.114(2) 0.7421(17) 0.039 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 2.0008(19) . ?
Zn1 O7 2.008(3) . ?
Zn1 O8 2.017(3) . ?
Zn1 O6 2.026(3) . ?
O9 H9A 0.863(18) . ?
O9 H9B 0.854(18) . ?
O1 C1 1.282(3) . ?
O2 C1 1.241(4) . ?
O3 C5 1.229(4) . ?
O4 C5 1.267(4) . ?
O5 C9 1.230(4) . ?
O8 H8A 0.863(19) . ?
O8 H8B 0.878(18) . ?
O7 H7B 0.867(18) . ?
O7 H7A 0.859(18) . ?
O6 H6B 0.876(18) . ?
O6 H6A 0.868(19) . ?
N1 C9 1.347(4) . ?
N1 C7 1.415(3) . ?
N1 H1N 0.8600 . ?
C1 C2 1.501(4) . ?
C2 C8 1.389(4) . ?
C2 C3 1.392(4) . ?
C3 C4 1.388(4) . ?
C3 H3 0.9300 . ?
C4 C6 1.390(4) . ?
C4 C5 1.511(4) . ?
C6 C7 1.390(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.395(4) . ?
C9 C10 1.512(4) . ?
C10 C11 1.499(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C8 H8 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 O7 119.09(13) . . ?
O1 Zn1 O8 104.48(11) . . ?
O7 Zn1 O8 116.52(13) . . ?
O1 Zn1 O6 101.33(10) . . ?
O7 Zn1 O6 105.30(13) . . ?
O8 Zn1 O6 108.80(12) . . ?
H9A O9 H9B 108(3) . . ?
C1 O1 Zn1 107.27(17) . . ?
Zn1 O8 H8A 119(3) . . ?
Zn1 O8 H8B 113(2) . . ?
H8A O8 H8B 103(4) . . ?
Zn1 O7 H7B 114(3) . . ?
Zn1 O7 H7A 113(2) . . ?
H7B O7 H7A 110(4) . . ?
Zn1 O6 H6B 109(2) . . ?
Zn1 O6 H6A 115(2) . . ?
H6B O6 H6A 106(3) . . ?
C9 N1 C7 129.2(2) . . ?
C9 N1 H1N 115.4 . . ?
C7 N1 H1N 115.4 . . ?
O2 C1 O1 122.5(2) . . ?
O2 C1 C2 120.1(2) . . ?
O1 C1 C2 117.3(2) . . ?
C8 C2 C3 119.7(2) . . ?
C8 C2 C1 121.8(2) . . ?
C3 C2 C1 118.5(2) . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C6 120.1(2) . . ?
C3 C4 C5 119.0(2) . . ?
C6 C4 C5 120.8(2) . . ?
O3 C5 O4 124.4(3) . . ?
O3 C5 C4 118.9(3) . . ?
O4 C5 C4 116.7(2) . . ?
C4 C6 C7 120.1(2) . . ?
C4 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C8 119.7(2) . . ?
C6 C7 N1 122.9(2) . . ?
C8 C7 N1 117.4(2) . . ?
O5 C9 N1 124.4(3) . . ?
O5 C9 C10 120.7(3) . . ?
N1 C9 C10 114.9(3) . . ?
C11 C10 C9 111.9(3) . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C9 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 . . ?
C2 C8 C7 120.3(2) . . ?
C2 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 C1 O2 -16.0(4) . . . . ?
Zn1 O1 C1 C2 162.2(2) . . . . ?
O2 C1 C2 C8 -162.1(3) . . . . ?
O1 C1 C2 C8 19.7(4) . . . . ?
O2 C1 C2 C3 19.3(4) . . . . ?
O1 C1 C2 C3 -158.9(3) . . . . ?
C8 C2 C3 C4 1.4(4) . . . . ?
C1 C2 C3 C4 -180.0(2) . . . . ?
C2 C3 C4 C6 -0.8(4) . . . . ?
C2 C3 C4 C5 177.7(3) . . . . ?
C3 C4 C5 O3 17.4(4) . . . . ?
C6 C4 C5 O3 -164.2(3) . . . . ?
C3 C4 C5 O4 -162.3(3) . . . . ?
C6 C4 C5 O4 16.2(4) . . . . ?
C3 C4 C6 C7 -0.4(4) . . . . ?
C5 C4 C6 C7 -178.8(3) . . . . ?
C4 C6 C7 C8 0.8(4) . . . . ?
C4 C6 C7 N1 -179.7(2) . . . . ?
C9 N1 C7 C6 2.1(4) . . . . ?
C9 N1 C7 C8 -178.3(3) . . . . ?
C7 N1 C9 O5 0.7(5) . . . . ?
C7 N1 C9 C10 -178.7(3) . . . . ?
O5 C9 C10 C11 -54.2(5) . . . . ?
N1 C9 C10 C11 125.3(3) . . . . ?
C3 C2 C8 C7 -0.9(4) . . . . ?
C1 C2 C8 C7 -179.5(2) . . . . ?
C6 C7 C8 C2 -0.2(4) . . . . ?
N1 C7 C8 C2 -179.7(2) . . . . ?

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
N1 H1N O2 0.86 2.15 2.987(3) 164.0 6_655
C6 H6 O5 0.93 2.26 2.877(3) 122.8 .
C8 H8 O2 0.93 2.65 3.402(3) 138.4 6_655
O9 H9A O4 0.863(18) 1.79(2) 2.647(3) 171(3) 1_545
O9 H9B O1 0.854(18) 2.02(2) 2.794(3) 150(3) 5_666
O6 H6B O9 0.876(18) 2.12(2) 2.924(4) 153(3) 5_666
O6 H6A O3 0.868(19) 2.09(2) 2.943(4) 166(3) 7_586
O8 H8A O4 0.863(19) 2.05(2) 2.905(3) 172(4) 7_586
O8 H8B O5 0.878(18) 2.35(2) 3.203(4) 163(3) 5_676
O7 H7B O3 0.867(18) 2.53(2) 3.330(4) 155(3) 2_476
O7 H7B O4 0.867(18) 2.43(3) 3.136(4) 139(3) 2_476
O7 H7A O9 0.859(18) 2.28(2) 3.131(4) 171(3) 4_565

_refine_diff_density_max         0.857
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.112

_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_compound2
_database_code_depnum_ccdc_archive 'CCDC 1040067'
_audit_update_record             
;
2014-12-17 deposited with the CCDC.
2015-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H15 N O8 Zn, 3(H2 O)'
_chemical_formula_sum            'C11 H21 N O11 Zn'
_chemical_formula_weight         408.66

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                   7.0755(2)
_cell_length_b                   11.1714(3)
_cell_length_c                   12.1991(4)
_cell_angle_alpha                73.1520(10)
_cell_angle_beta                 82.4800(9)
_cell_angle_gamma                72.0420(10)
_cell_volume                     877.00(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9034
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      28.30

_exptl_crystal_description       Plates
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.454
_shelx_estimated_absorpt_T_min   0.686
_shelx_estimated_absorpt_T_max   0.811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7
_exptl_absorpt_correction_T_max  0.8
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17801
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.973
_diffrn_reflns_theta_max         28.311
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4353
_reflns_number_gt                3816
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0750P)²+0.4628P] 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         4353
_refine_ls_number_parameters     272
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1258
_refine_ls_wR_factor_gt          0.1198
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.100
_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 0.00992(4) 0.41619(2) 0.22167(2) 0.03688(12) Uani 1 1 d . . . . .
O1 O 0.0880(3) 0.31325(18) 0.02595(19) 0.0528(5) Uani 1 1 d . . . . .
O2 O 0.1066(3) 0.23352(17) 0.21387(18) 0.0490(5) Uani 1 1 d . . . . .
O3 O 0.3967(3) -0.37369(17) 0.28430(15) 0.0462(5) Uani 1 1 d . . . . .
O4 O 0.4123(4) -0.23714(19) 0.37970(17) 0.0637(7) Uani 1 1 d . . . . .
O5 O 0.4123(3) -0.2999(2) -0.10299(17) 0.0514(5) Uani 1 1 d . . . . .
O6 O -0.2551(3) 0.5053(2) 0.1506(2) 0.0549(5) Uani 1 1 d D . . . .
O7 O 0.2084(3) 0.5141(2) 0.14564(19) 0.0548(5) Uani 1 1 d D . . . .
O8 O -0.0098(4) 0.3933(3) 0.3922(2) 0.0722(7) Uani 1 1 d D . . . .
N1 N 0.2972(3) -0.0806(2) -0.13030(17) 0.0422(5) Uani 1 1 d . . . . .
C1 C 0.1271(3) 0.2198(2) 0.1122(2) 0.0375(5) Uani 1 1 d . . . . .
C2 C 0.2024(3) 0.0828(2) 0.1010(2) 0.0331(4) Uani 1 1 d . . . . .
C3 C 0.2565(3) -0.0218(2) 0.1976(2) 0.0335(4) Uani 1 1 d . . . . .
H3 H 0.2485 -0.0067 0.2694 0.040 Uiso 1 1 calc R U . . .
C4 C 0.3225(3) -0.1486(2) 0.18643(19) 0.0315(4) Uani 1 1 d . . . . .
C5 C 0.3791(4) -0.2618(2) 0.2913(2) 0.0370(5) Uani 1 1 d . . . . .
C6 C 0.3366(3) -0.1716(2) 0.07907(19) 0.0320(4) Uani 1 1 d . . . . .
H6 H 0.3793 -0.2566 0.0719 0.038 Uiso 1 1 calc R U . . .
C7 C 0.2864(3) -0.0668(2) -0.01781(19) 0.0324(4) Uani 1 1 d . . . . .
C8 C 0.2182(3) 0.0598(2) -0.0055(2) 0.0347(5) Uani 1 1 d . . . . .
H8 H 0.1829 0.1297 -0.0698 0.042 Uiso 1 1 calc R U . . .
C9 C 0.3549(4) -0.1897(3) -0.1668(2) 0.0438(6) Uani 1 1 d D . . . .
C10A C 0.3331(9) -0.1757(8) -0.2949(4) 0.0539(15) Uani 0.660(10) 1 d D . P A 1
H10A H 0.3395 -0.2602 -0.3043 0.065 Uiso 0.660(10) 1 calc R U P A 1
H10B H 0.2034 -0.1169 -0.3177 0.065 Uiso 0.660(10) 1 calc R U P A 1
O11 O 0.1907(6) 0.1765(4) 0.6888(3) 0.0902(9) Uani 1 1 d D . . . .
O9 O 0.3198(4) 0.4433(3) 0.4793(2) 0.0731(7) Uani 1 1 d D . . . .
O10 O 0.9683(5) 0.1225(3) 0.5262(3) 0.0814(8) Uani 1 1 d D . . . .
C11A C 0.4890(9) -0.1254(8) -0.3720(4) 0.071(2) Uani 0.660(10) 1 d D U P A 1
H11A H 0.6159 -0.1677 -0.3382 0.106 Uiso 0.660(10) 1 calc R U P A 1
H11B H 0.4578 -0.0330 -0.3826 0.106 Uiso 0.660(10) 1 calc R U P A 1
H11C H 0.4937 -0.1432 -0.4449 0.106 Uiso 0.660(10) 1 calc R U P A 1
C10B C 0.351(3) -0.1423(15) -0.2903(11) 0.070(5) Uiso 0.340(10) 1 d D . P A 2
H10C H 0.4002 -0.0663 -0.3148 0.084 Uiso 0.340(10) 1 calc R U P A 2
H10D H 0.2142 -0.1151 -0.3125 0.084 Uiso 0.340(10) 1 calc R U P A 2
C11B C 0.469(2) -0.2387(13) -0.3490(8) 0.079(5) Uani 0.340(10) 1 d D U P A 2
H11D H 0.6063 -0.2425 -0.3511 0.118 Uiso 0.340(10) 1 calc R U P A 2
H11E H 0.4257 -0.2147 -0.4259 0.118 Uiso 0.340(10) 1 calc R U P A 2
H11F H 0.4514 -0.3226 -0.3090 0.118 Uiso 0.340(10) 1 calc R U P A 2
H1N H 0.270(9) -0.002(6) -0.188(5) 0.118 Uiso 1 1 d . U . . .
H6A H -0.356(6) 0.541(5) 0.197(4) 0.118 Uiso 1 1 d D U . . .
H7A H 0.263(9) 0.558(5) 0.197(5) 0.118 Uiso 1 1 d . U . . .
H6B H -0.240(8) 0.566(4) 0.084(3) 0.118 Uiso 1 1 d D U . . .
H7B H 0.153(8) 0.584(4) 0.089(4) 0.118 Uiso 1 1 d D U . . .
H8B H -0.108(6) 0.436(5) 0.433(4) 0.118 Uiso 1 1 d D U . . .
H8A H 0.092(6) 0.408(6) 0.420(5) 0.118 Uiso 1 1 d D U . . .
H9A H 0.411(6) 0.389(4) 0.521(4) 0.118 Uiso 1 1 d D U . . .
H9B H 0.373(7) 0.492(4) 0.428(4) 0.118 Uiso 1 1 d D U . . .
H11H H 0.305(4) 0.183(5) 0.660(5) 0.118 Uiso 1 1 d D U . . .
H11G H 0.118(7) 0.253(3) 0.691(5) 0.118 Uiso 1 1 d D U . . .
H10H H 0.845(3) 0.163(5) 0.536(5) 0.118 Uiso 1 1 d D U . . .
H10G H 1.042(6) 0.135(6) 0.569(4) 0.118 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O2 1.9688(18) . ?
Zn1 O6 2.009(2) . ?
Zn1 O7 2.011(2) . ?
Zn1 O8 2.013(3) . ?
O1 C1 1.239(3) . ?
O2 C1 1.277(3) . ?
O3 C5 1.245(3) . ?
O4 C5 1.253(3) . ?
O5 C9 1.227(4) . ?
O6 H6A 0.91(2) . ?
O6 H6B 0.91(2) . ?
O7 H7A 1.07(6) . ?
O7 H7B 0.90(2) . ?
O8 H8B 0.89(2) . ?
O8 H8A 0.91(2) . ?
N1 C9 1.346(4) . ?
N1 C7 1.415(3) . ?
N1 H1N 0.94(6) . ?
C1 C2 1.499(3) . ?
C2 C8 1.380(4) . ?
C2 C3 1.394(3) . ?
C3 C4 1.390(3) . ?
C3 H3 0.9300 . ?
C4 C6 1.391(3) . ?
C4 C5 1.510(3) . ?
C6 C7 1.395(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.392(3) . ?
C8 H8 0.9300 . ?
C9 C10B 1.445(13) . ?
C9 C10A 1.548(5) . ?
C10A C11A 1.490(8) . ?
C10A H10A 0.9700 . ?
C10A H10B 0.9700 . ?
O11 H11H 0.852(19) . ?
O11 H11G 0.855(19) . ?
O9 H9A 0.846(19) . ?
O9 H9B 0.834(19) . ?
O10 H10H 0.858(19) . ?
O10 H10G 0.853(19) . ?
C11A H11A 0.9600 . ?
C11A H11B 0.9600 . ?
C11A H11C 0.9600 . ?
C10B C11B 1.451(14) . ?
C10B H10C 0.9700 . ?
C10B H10D 0.9700 . ?
C11B H11D 0.9600 . ?
C11B H11E 0.9600 . ?
C11B H11F 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
O2 Zn1 O6 110.91(9) . . ?
O2 Zn1 O7 110.96(10) . . ?
O6 Zn1 O7 110.51(9) . . ?
O2 Zn1 O8 101.26(11) . . ?
O6 Zn1 O8 112.13(11) . . ?
O7 Zn1 O8 110.76(11) . . ?
C1 O2 Zn1 114.21(15) . . ?
Zn1 O6 H6A 116(4) . . ?
Zn1 O6 H6B 109(4) . . ?
H6A O6 H6B 111(5) . . ?
Zn1 O7 H7A 117(3) . . ?
Zn1 O7 H7B 111(4) . . ?
H7A O7 H7B 101(4) . . ?
Zn1 O8 H8B 127(4) . . ?
Zn1 O8 H8A 115(4) . . ?
H8B O8 H8A 97(5) . . ?
C9 N1 C7 129.5(2) . . ?
C9 N1 H1N 115(3) . . ?
C7 N1 H1N 115(3) . . ?
O1 C1 O2 123.0(2) . . ?
O1 C1 C2 120.5(2) . . ?
O2 C1 C2 116.5(2) . . ?
C8 C2 C3 119.8(2) . . ?
C8 C2 C1 119.8(2) . . ?
C3 C2 C1 120.4(2) . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C6 120.3(2) . . ?
C3 C4 C5 119.8(2) . . ?
C6 C4 C5 119.97(19) . . ?
O3 C5 O4 123.9(2) . . ?
O3 C5 C4 118.7(2) . . ?
O4 C5 C4 117.4(2) . . ?
C4 C6 C7 119.8(2) . . ?
C4 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 119.4(2) . . ?
C8 C7 N1 116.8(2) . . ?
C6 C7 N1 123.8(2) . . ?
C2 C8 C7 120.8(2) . . ?
C2 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
O5 C9 N1 123.6(2) . . ?
O5 C9 C10B 131.9(6) . . ?
N1 C9 C10B 104.2(6) . . ?
O5 C9 C10A 118.3(4) . . ?
N1 C9 C10A 118.0(4) . . ?
C11A C10A C9 113.2(4) . . ?
C11A C10A H10A 108.9 . . ?
C9 C10A H10A 108.9 . . ?
C11A C10A H10B 108.9 . . ?
C9 C10A H10B 108.9 . . ?
H10A C10A H10B 107.7 . . ?
H11H O11 H11G 108(4) . . ?
H9A O9 H9B 107(4) . . ?
H10H O10 H10G 112(4) . . ?
C10A C11A H11A 109.5 . . ?
C10A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C10A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C9 C10B C11B 113.3(11) . . ?
C9 C10B H10C 108.9 . . ?
C11B C10B H10C 108.9 . . ?
C9 C10B H10D 108.9 . . ?
C11B C10B H10D 108.9 . . ?
H10C C10B H10D 107.7 . . ?
C10B C11B H11D 109.5 . . ?
C10B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C10B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 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 O2 C1 O1 -0.6(3) . . . . ?
Zn1 O2 C1 C2 179.40(15) . . . . ?
O1 C1 C2 C8 -3.5(3) . . . . ?
O2 C1 C2 C8 176.5(2) . . . . ?
O1 C1 C2 C3 176.5(2) . . . . ?
O2 C1 C2 C3 -3.5(3) . . . . ?
C8 C2 C3 C4 -1.2(3) . . . . ?
C1 C2 C3 C4 178.8(2) . . . . ?
C2 C3 C4 C6 0.6(4) . . . . ?
C2 C3 C4 C5 -179.4(2) . . . . ?
C3 C4 C5 O3 164.9(2) . . . . ?
C6 C4 C5 O3 -15.1(4) . . . . ?
C3 C4 C5 O4 -17.5(4) . . . . ?
C6 C4 C5 O4 162.5(3) . . . . ?
C3 C4 C6 C7 0.8(4) . . . . ?
C5 C4 C6 C7 -179.3(2) . . . . ?
C4 C6 C7 C8 -1.5(3) . . . . ?
C4 C6 C7 N1 179.6(2) . . . . ?
C9 N1 C7 C8 -179.3(3) . . . . ?
C9 N1 C7 C6 -0.4(4) . . . . ?
C3 C2 C8 C7 0.5(3) . . . . ?
C1 C2 C8 C7 -179.5(2) . . . . ?
C6 C7 C8 C2 0.9(3) . . . . ?
N1 C7 C8 C2 179.9(2) . . . . ?
C7 N1 C9 O5 -0.9(5) . . . . ?
C7 N1 C9 C10B -175.3(8) . . . . ?
C7 N1 C9 C10A 174.5(3) . . . . ?
O5 C9 C10A C11A -108.0(6) . . . . ?
N1 C9 C10A C11A 76.3(6) . . . . ?
C10B C9 C10A C11A 40(3) . . . . ?
O5 C9 C10B C11B -13(2) . . . . ?
N1 C9 C10B C11B 160.6(12) . . . . ?
C10A C9 C10B C11B -52(2) . . . . ?

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
C6 H6 O5 0.93 2.29 2.887(3) 121.6 .
C10B H10C O11 0.97 2.67 3.332(15) 125.8 1_554
N1 H1N O11 0.94(6) 2.08(6) 3.019(4) 176(5) 1_554
O6 H6A O3 0.91(2) 2.05(2) 2.955(3) 174(5) 1_465
O7 H7A O3 1.07(6) 1.95(6) 3.010(3) 173(5) 1_565
O6 H6B O1 0.91(2) 2.06(3) 2.902(3) 153(5) 2_565
O7 H7B O1 0.90(2) 2.16(3) 2.969(3) 149(5) 2_565
O8 H8B O9 0.89(2) 2.10(2) 2.982(5) 172(6) 2_566
O8 H8A O9 0.91(2) 2.03(2) 2.944(4) 179(6) .
O9 H9A O4 0.846(19) 1.95(2) 2.779(3) 167(5) 2_656
O9 H9B O3 0.834(19) 1.98(3) 2.768(3) 158(5) 1_565
O11 H11H O4 0.852(19) 2.22(3) 3.046(5) 162(5) 2_656
O10 H10H O4 0.858(19) 2.03(3) 2.851(4) 159(5) 2_656
O10 H10G O11 0.853(19) 2.13(2) 2.978(5) 172(5) 1_655

_refine_diff_density_max         0.973
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.114

_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_Compound3
_database_code_depnum_ccdc_archive 'CCDC 1040068'
_audit_update_record             
;
2014-12-17 deposited with the CCDC.
2015-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 N O7 Zn'
_chemical_formula_sum            'C15 H13 N O7 Zn'
_chemical_formula_weight         384.63

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   5.2989(5)
_cell_length_b                   15.3102(12)
_cell_length_c                   19.3432(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1569.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      28.27

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    1.603
_shelx_estimated_absorpt_T_min   0.620
_shelx_estimated_absorpt_T_max   0.730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6
_exptl_absorpt_correction_T_max  0.7
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18056
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.491
_diffrn_reflns_theta_max         28.337
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             3780
_reflns_number_gt                3691
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_max     0.958
_reflns_Friedel_fraction_full    0.969

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0639P)²+0.2826P] 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_abs_structure_details 
;
 Flack x determined using 1515 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3780
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0893
_refine_ls_wR_factor_gt          0.0883
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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 0.11229(6) 0.09546(2) 0.10540(2) 0.03187(12) Uani 1 1 d . . . . .
O1 O -0.1305(5) 0.04009(16) 0.16875(14) 0.0482(6) Uani 1 1 d . . . . .
O2 O -0.0073(8) -0.0960(2) 0.1510(2) 0.0815(12) Uani 1 1 d . . . . .
O3 O 0.2214(6) 0.19023(18) 0.16644(13) 0.0488(6) Uani 1 1 d . . . . .
O4 O 0.4826(6) 0.22627(16) 0.08133(12) 0.0441(5) Uani 1 1 d . . . . .
O6 O 0.3772(6) 0.0073(2) 0.08052(14) 0.0526(6) Uani 1 1 d . . . . .
C2 C -0.1313(6) -0.0414(2) 0.18169(15) 0.0340(6) Uani 1 1 d . . . . .
C3 C 0.3058(5) 0.43165(19) 0.26046(14) 0.0307(5) Uani 1 1 d . . . . .
C4 C 0.3780(6) 0.24165(19) 0.13775(14) 0.0328(5) Uani 1 1 d . . . . .
C5 C 0.4281(6) 0.32612(19) 0.17437(14) 0.0312(5) Uani 1 1 d . . . . .
C6 C 0.6239(6) 0.38089(19) 0.15265(14) 0.0317(5) Uani 1 1 d . . . . .
H6 H 0.7301 0.3638 0.1169 0.038 Uiso 1 1 calc R U . . .
C7 C 0.6589(5) 0.46151(19) 0.18510(14) 0.0307(5) Uani 1 1 d . . . . .
C8 C 0.4970(6) 0.4866(2) 0.23857(14) 0.0315(5) Uani 1 1 d . . . . .
H8 H 0.5180 0.5408 0.2596 0.038 Uiso 1 1 calc R U . . .
C9 C 0.2703(6) 0.3514(2) 0.22866(15) 0.0317(6) Uani 1 1 d . . . . .
H9 H 0.1417 0.3145 0.2434 0.038 Uiso 1 1 calc R U . . .
N1 N 0.8516(6) 0.52226(19) 0.16773(13) 0.0375(6) Uani 1 1 d . . . . .
C11 C 1.0007(6) 0.5250(2) 0.11170(15) 0.0333(5) Uani 1 1 d . . . . .
O7 O 0.9967(6) 0.46875(19) 0.06625(12) 0.0527(7) Uani 1 1 d . . . . .
C13 C 1.1797(5) 0.6008(2) 0.10719(15) 0.0348(5) Uani 1 1 d . . . . .
C14 C 1.1988(8) 0.6646(3) 0.1580(2) 0.0530(9) Uani 1 1 d . . . . .
H14 H 1.0947 0.6626 0.1966 0.064 Uiso 1 1 calc R U . . .
C15 C 1.3742(11) 0.7314(3) 0.1506(2) 0.0650(12) Uani 1 1 d . . . . .
H15 H 1.3876 0.7736 0.1850 0.078 Uiso 1 1 calc R U . . .
C16 C 1.5276(8) 0.7364(3) 0.0940(3) 0.0611(11) Uani 1 1 d . . . . .
H16 H 1.6451 0.7812 0.0901 0.073 Uiso 1 1 calc R U . . .
C17 C 1.5060(9) 0.6736(3) 0.0421(3) 0.0623(11) Uani 1 1 d . . . . .
H17 H 1.6076 0.6766 0.0029 0.075 Uiso 1 1 calc R U . . .
C18 C 1.3320(8) 0.6068(3) 0.0493(2) 0.0510(8) Uani 1 1 d . . . . .
H18 H 1.3172 0.5652 0.0146 0.061 Uiso 1 1 calc R U . . .
O5 O -0.0913(6) 0.1366(2) 0.02347(14) 0.0541(7) Uani 1 1 d . . . . .
H6B H 0.4108 0.0117 0.0315 0.081 Uiso 1 1 d . U . . .
H5A H -0.0322 0.1800 -0.0077 0.081 Uiso 1 1 d . U . . .
H6A H 0.3527 -0.0476 0.0972 0.081 Uiso 1 1 d . U . . .
H5B H -0.2502 0.1603 0.0348 0.081 Uiso 1 1 d . U . . .
H1N H 0.842(12) 0.565(4) 0.188(3) 0.081 Uiso 1 1 d . 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 1.958(2) . ?
Zn1 O1 1.969(2) . ?
Zn1 O6 2.006(3) . ?
Zn1 O5 2.018(3) . ?
O1 C2 1.273(4) . ?
O2 C2 1.217(4) . ?
O3 C4 1.271(4) . ?
O4 C4 1.247(4) . ?
O6 H6B 0.97000 . ?
O6 H6A 0.91000 . ?
C2 C3 1.509(4) 3_545 ?
C3 C8 1.384(4) . ?
C3 C9 1.387(4) . ?
C3 C2 1.509(4) 3 ?
C4 C5 1.498(4) . ?
C5 C9 1.397(4) . ?
C5 C6 1.399(4) . ?
C6 C7 1.397(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.398(4) . ?
C7 N1 1.421(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
N1 C11 1.342(4) . ?
N1 H1N 0.76(6) . ?
C11 O7 1.231(4) . ?
C11 C13 1.502(4) . ?
C13 C18 1.383(5) . ?
C13 C14 1.389(5) . ?
C14 C15 1.389(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.366(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.395(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
O5 H5A 0.95000 . ?
O5 H5B 0.94000 . ?

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 97.86(11) . . ?
O3 Zn1 O6 115.88(13) . . ?
O1 Zn1 O6 108.49(11) . . ?
O3 Zn1 O5 113.58(13) . . ?
O1 Zn1 O5 105.90(13) . . ?
O6 Zn1 O5 113.31(12) . . ?
C2 O1 Zn1 123.1(2) . . ?
C4 O3 Zn1 112.86(19) . . ?
Zn1 O6 H6B 108.00 . . ?
Zn1 O6 H6A 116.00 . . ?
H6B O6 H6A 116.00 . . ?
O2 C2 O1 125.1(3) . . ?
O2 C2 C3 120.4(3) . 3_545 ?
O1 C2 C3 114.5(3) . 3_545 ?
C8 C3 C9 120.2(3) . . ?
C8 C3 C2 120.6(3) . 3 ?
C9 C3 C2 119.2(3) . 3 ?
O4 C4 O3 123.7(3) . . ?
O4 C4 C5 119.9(3) . . ?
O3 C4 C5 116.3(3) . . ?
C9 C5 C6 120.2(3) . . ?
C9 C5 C4 119.3(3) . . ?
C6 C5 C4 120.4(2) . . ?
C5 C6 C7 119.5(3) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C8 C7 C6 119.6(3) . . ?
C8 C7 N1 115.8(3) . . ?
C6 C7 N1 124.6(3) . . ?
C3 C8 C7 120.6(3) . . ?
C3 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C3 C9 C5 119.8(3) . . ?
C3 C9 H9 120.1 . . ?
C5 C9 H9 120.1 . . ?
C11 N1 C7 129.4(3) . . ?
C11 N1 H1N 115(5) . . ?
C7 N1 H1N 113(5) . . ?
O7 C11 N1 123.0(3) . . ?
O7 C11 C13 120.7(3) . . ?
N1 C11 C13 116.3(3) . . ?
C18 C13 C14 118.9(3) . . ?
C18 C13 C11 117.9(3) . . ?
C14 C13 C11 123.3(3) . . ?
C13 C14 C15 119.6(4) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 121.4(4) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 119.3(4) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C18 C17 C16 119.4(4) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C13 C18 C17 121.4(4) . . ?
C13 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
Zn1 O5 H5A 123.00 . . ?
Zn1 O5 H5B 115.00 . . ?
H5A O5 H5B 100.00 . . ?

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 C2 O2 -9.6(6) . . . . ?
Zn1 O1 C2 C3 171.1(2) . . . 3_545 ?
Zn1 O3 C4 O4 -10.9(4) . . . . ?
Zn1 O3 C4 C5 167.0(2) . . . . ?
O4 C4 C5 C9 165.7(3) . . . . ?
O3 C4 C5 C9 -12.3(4) . . . . ?
O4 C4 C5 C6 -11.6(4) . . . . ?
O3 C4 C5 C6 170.4(3) . . . . ?
C9 C5 C6 C7 -0.7(4) . . . . ?
C4 C5 C6 C7 176.6(3) . . . . ?
C5 C6 C7 C8 -0.4(4) . . . . ?
C5 C6 C7 N1 179.7(3) . . . . ?
C9 C3 C8 C7 -1.1(4) . . . . ?
C2 C3 C8 C7 179.8(3) 3 . . . ?
C6 C7 C8 C3 1.3(4) . . . . ?
N1 C7 C8 C3 -178.8(3) . . . . ?
C8 C3 C9 C5 0.0(4) . . . . ?
C2 C3 C9 C5 179.1(3) 3 . . . ?
C6 C5 C9 C3 0.9(4) . . . . ?
C4 C5 C9 C3 -176.4(3) . . . . ?
C8 C7 N1 C11 -165.6(3) . . . . ?
C6 C7 N1 C11 14.3(5) . . . . ?
C7 N1 C11 O7 -3.5(6) . . . . ?
C7 N1 C11 C13 177.3(3) . . . . ?
O7 C11 C13 C18 2.4(5) . . . . ?
N1 C11 C13 C18 -178.5(3) . . . . ?
O7 C11 C13 C14 -177.7(4) . . . . ?
N1 C11 C13 C14 1.4(5) . . . . ?
C18 C13 C14 C15 -1.8(6) . . . . ?
C11 C13 C14 C15 178.3(4) . . . . ?
C13 C14 C15 C16 0.7(8) . . . . ?
C14 C15 C16 C17 0.6(8) . . . . ?
C15 C16 C17 C18 -0.8(8) . . . . ?
C14 C13 C18 C17 1.6(6) . . . . ?
C11 C13 C18 C17 -178.5(4) . . . . ?
C16 C17 C18 C13 -0.3(7) . . . . ?

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
C6 H6 O7 0.93 2.35 2.916(4) 118.7 .
O6 H6B O7 0.97000 1.97000 2.932(4) 174.4(2) 2_455
O5 H5A O4 0.95000 2.02000 2.944(4) 162.8(2) 2_455
O6 H6A O2 0.91000 2.30000 2.917(4) 125.00 .
O5 H5B O4 0.94000 1.96000 2.870(4) 162.1(2) 1_455
C6 H6 O7 0.93 2.35 2.916(4) 118.7 .
O6 H6B O7 0.97000 1.97000 2.932(4) 174.4(2) 2_455
O5 H5A O4 0.95000 2.02000 2.944(4) 162.8(2) 2_455
O6 H6A O2 0.91000 2.3000 2.917(4) 125.00 .
O5 H5B O4 0.94000 1.96000 2.870(4) 162.1(2) 1_455

_refine_diff_density_max         1.074
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.086

_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_compound4
_database_code_depnum_ccdc_archive 'CCDC 1040069'
_audit_update_record             
;
2014-12-17 deposited with the CCDC.
2015-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 N O7 Zn, 2(H2 O)'
_chemical_formula_sum            'C15 H17 N O9 Zn'
_chemical_formula_weight         420.66

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                   8.9796(17)
_cell_length_b                   10.1531(16)
_cell_length_c                   10.6054(18)
_cell_angle_alpha                89.721(7)
_cell_angle_beta                 77.398(7)
_cell_angle_gamma                71.835(6)
_cell_volume                     894.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4558
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      26.18

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.421
_shelx_estimated_absorpt_T_min   0.736
_shelx_estimated_absorpt_T_max   0.784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.73
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17485
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.452
_diffrn_reflns_theta_max         26.390
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3668
_reflns_number_gt                2853
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0547P)²+0.3126P] 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         3668
_refine_ls_number_parameters     263
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1030
_refine_ls_wR_factor_gt          0.0940
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.059
_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 0.71439(4) 0.45126(3) 0.57280(3) 0.02978(13) Uani 1 1 d . . . . .
O1 O 0.5621(2) 0.64172(19) 0.6290(2) 0.0327(5) Uani 1 1 d . . . . .
O2 O 0.7768(3) 0.6929(2) 0.5261(2) 0.0431(6) Uani 1 1 d . . . . .
O4 O 0.5685(2) 1.34274(19) 0.6529(2) 0.0342(5) Uani 1 1 d . . . . .
O3 O 0.7936(3) 1.1717(2) 0.5777(2) 0.0427(6) Uani 1 1 d . . . . .
O5 O 0.1405(3) 1.2609(3) 0.9569(3) 0.0597(7) Uani 1 1 d . . . . .
O6 O 0.9029(4) 0.4106(3) 0.6562(3) 0.0621(7) Uani 1 1 d D . . . .
O7 O 0.7365(3) 0.4309(3) 0.3800(3) 0.0566(7) Uani 1 1 d D . . . .
N1 N 0.1466(3) 1.1008(3) 0.8084(3) 0.0317(6) Uani 1 1 d . . . . .
C1 C 0.6382(3) 0.7278(3) 0.5928(3) 0.0278(6) Uani 1 1 d . . . . .
C2 C 0.5505(3) 0.8783(3) 0.6384(3) 0.0250(6) Uani 1 1 d . . . . .
C3 C 0.3906(3) 0.9216(3) 0.7054(3) 0.0279(6) Uani 1 1 d . . . . .
H3 H 0.3353 0.8575 0.7223 0.034 Uiso 1 1 calc R U . . .
C4 C 0.3127(3) 1.0606(3) 0.7475(3) 0.0262(6) Uani 1 1 d . . . . .
C5 C 0.3958(4) 1.1557(3) 0.7253(3) 0.0288(6) Uani 1 1 d . . . . .
H5 H 0.3446 1.2484 0.7549 0.035 Uiso 1 1 calc R U . . .
C6 C 0.5559(3) 1.1124(3) 0.6587(3) 0.0257(6) Uani 1 1 d . . . . .
C7 C 0.6323(3) 0.9735(3) 0.6151(3) 0.0269(6) Uani 1 1 d . . . . .
H7 H 0.7393 0.9448 0.5699 0.032 Uiso 1 1 calc R U . . .
C10 C 0.0705(4) 1.1961(3) 0.9077(3) 0.0371(7) Uani 1 1 d . . . . .
C11 C -0.1060(4) 1.2219(4) 0.9548(3) 0.0403(8) Uani 1 1 d . . . . .
C12 C -0.1827(4) 1.1271(4) 0.9330(3) 0.0500(9) Uani 1 1 d . . . . .
H12 H -0.1225 1.0415 0.8892 0.060 Uiso 1 1 calc R U . . .
C13 C -0.3478(5) 1.1589(6) 0.9760(4) 0.0652(12) Uani 1 1 d . . . . .
H13 H -0.3984 1.0953 0.9608 0.078 Uiso 1 1 calc R U . . .
C14 C -0.4372(5) 1.2866(6) 1.0421(4) 0.0746(15) Uani 1 1 d . . . . .
H14 H -0.5482 1.3089 1.0703 0.090 Uiso 1 1 calc R U . . .
C15 C -0.3628(5) 1.3796(5) 1.0659(4) 0.0690(13) Uani 1 1 d . . . . .
H15 H -0.4233 1.4640 1.1118 0.083 Uiso 1 1 calc R U . . .
C16 C -0.1994(5) 1.3494(4) 1.0225(3) 0.0533(10) Uani 1 1 d . . . . .
H16 H -0.1503 1.4139 1.0382 0.064 Uiso 1 1 calc R U . . .
C9 C 0.6461(4) 1.2141(3) 0.6285(3) 0.0287(6) Uani 1 1 d . . . . .
O8 O 0.9902(3) 0.0619(3) 0.3362(3) 0.0536(7) Uani 1 1 d D . . . .
O9 O 0.0838(4) 0.3241(4) 0.2219(3) 0.0693(8) Uani 1 1 d D . . . .
H6A H 0.908(7) 0.483(4) 0.702(5) 0.104 Uiso 1 1 d D U . . .
H6B H 0.993(4) 0.366(5) 0.597(4) 0.104 Uiso 1 1 d D U . . .
H7A H 0.665(5) 0.394(5) 0.360(5) 0.104 Uiso 1 1 d D U . . .
H7B H 0.838(3) 0.402(6) 0.336(5) 0.104 Uiso 1 1 d D U . . .
H1N H 0.098(4) 1.062(4) 0.775(3) 0.038(10) Uiso 1 1 d . . . . .
H9B H 0.109(5) 0.312(4) 0.1361(19) 0.058 Uiso 1 1 d D U . . .
H8B H 0.915(4) 0.092(4) 0.407(3) 0.058 Uiso 1 1 d D U . . .
H8A H 1.052(4) -0.012(3) 0.366(4) 0.058 Uiso 1 1 d D U . . .
H9A H 0.085(5) 0.246(3) 0.257(4) 0.058 Uiso 1 1 d D 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 1.9929(19) . ?
Zn1 O6 2.008(3) . ?
Zn1 O4 2.014(2) 1_545 ?
Zn1 O7 2.016(3) . ?
O1 C1 1.278(3) . ?
O2 C1 1.232(4) . ?
O4 C9 1.271(3) . ?
O4 Zn1 2.014(2) 1_565 ?
O3 C9 1.251(4) . ?
O5 C10 1.228(4) . ?
O6 H6A 0.90(2) . ?
O6 H6B 0.90(2) . ?
O7 H7A 0.901(19) . ?
O7 H7B 0.89(2) . ?
N1 C10 1.340(4) . ?
N1 C4 1.418(4) . ?
N1 H1N 0.80(4) . ?
C1 C2 1.510(4) . ?
C2 C7 1.377(4) . ?
C2 C3 1.387(4) . ?
C3 C4 1.391(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(4) . ?
C5 C6 1.387(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.392(4) . ?
C6 C9 1.494(4) . ?
C7 H7 0.9300 . ?
C10 C11 1.492(5) . ?
C11 C12 1.393(5) . ?
C11 C16 1.401(5) . ?
C12 C13 1.385(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.389(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.368(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
O8 H8B 0.873(19) . ?
O8 H8A 0.886(19) . ?
O9 H9B 0.889(19) . ?
O9 H9A 0.877(19) . ?

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 O6 110.90(11) . . ?
O1 Zn1 O4 98.19(8) . 1_545 ?
O6 Zn1 O4 109.78(11) . 1_545 ?
O1 Zn1 O7 105.39(10) . . ?
O6 Zn1 O7 123.51(12) . . ?
O4 Zn1 O7 106.03(10) 1_545 . ?
C1 O1 Zn1 107.54(17) . . ?
C9 O4 Zn1 108.22(18) . 1_565 ?
Zn1 O6 H6A 115(4) . . ?
Zn1 O6 H6B 109(4) . . ?
H6A O6 H6B 115(5) . . ?
Zn1 O7 H7A 112(4) . . ?
Zn1 O7 H7B 113(4) . . ?
H7A O7 H7B 120(5) . . ?
C10 N1 C4 126.3(3) . . ?
C10 N1 H1N 121(3) . . ?
C4 N1 H1N 113(3) . . ?
O2 C1 O1 123.3(2) . . ?
O2 C1 C2 120.3(2) . . ?
O1 C1 C2 116.4(2) . . ?
C7 C2 C3 119.5(2) . . ?
C7 C2 C1 119.1(2) . . ?
C3 C2 C1 121.3(2) . . ?
C2 C3 C4 120.3(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 N1 122.0(2) . . ?
C3 C4 N1 118.0(2) . . ?
C4 C5 C6 119.7(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 119.9(3) . . ?
C5 C6 C9 120.7(2) . . ?
C7 C6 C9 119.3(3) . . ?
C2 C7 C6 120.5(3) . . ?
C2 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
O5 C10 N1 122.3(3) . . ?
O5 C10 C11 121.1(3) . . ?
N1 C10 C11 116.6(3) . . ?
C12 C11 C16 118.5(4) . . ?
C12 C11 C10 123.4(3) . . ?
C16 C11 C10 118.1(3) . . ?
C13 C12 C11 120.7(4) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.4(5) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 120.4(4) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.5(4) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 120.5(4) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
O3 C9 O4 121.8(3) . . ?
O3 C9 C6 119.8(2) . . ?
O4 C9 C6 118.4(3) . . ?
H8B O8 H8A 99(4) . . ?
H9B O9 H9A 111(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O1 C1 O2 5.4(4) . . . . ?
Zn1 O1 C1 C2 -173.48(19) . . . . ?
O2 C1 C2 C7 -6.1(4) . . . . ?
O1 C1 C2 C7 172.8(3) . . . . ?
O2 C1 C2 C3 175.2(3) . . . . ?
O1 C1 C2 C3 -5.9(4) . . . . ?
C7 C2 C3 C4 0.8(4) . . . . ?
C1 C2 C3 C4 179.4(3) . . . . ?
C2 C3 C4 C5 -1.6(4) . . . . ?
C2 C3 C4 N1 176.2(3) . . . . ?
C10 N1 C4 C5 -38.8(5) . . . . ?
C10 N1 C4 C3 143.5(3) . . . . ?
C3 C4 C5 C6 1.3(4) . . . . ?
N1 C4 C5 C6 -176.3(3) . . . . ?
C4 C5 C6 C7 -0.3(4) . . . . ?
C4 C5 C6 C9 177.3(3) . . . . ?
C3 C2 C7 C6 0.3(4) . . . . ?
C1 C2 C7 C6 -178.4(3) . . . . ?
C5 C6 C7 C2 -0.5(4) . . . . ?
C9 C6 C7 C2 -178.1(3) . . . . ?
C4 N1 C10 O5 0.4(5) . . . . ?
C4 N1 C10 C11 179.3(3) . . . . ?
O5 C10 C11 C12 -159.6(4) . . . . ?
N1 C10 C11 C12 21.5(5) . . . . ?
O5 C10 C11 C16 21.6(5) . . . . ?
N1 C10 C11 C16 -157.4(3) . . . . ?
C16 C11 C12 C13 0.8(5) . . . . ?
C10 C11 C12 C13 -178.1(3) . . . . ?
C11 C12 C13 C14 -0.3(6) . . . . ?
C12 C13 C14 C15 -0.8(6) . . . . ?
C13 C14 C15 C16 1.4(7) . . . . ?
C14 C15 C16 C11 -0.9(6) . . . . ?
C12 C11 C16 C15 -0.2(5) . . . . ?
C10 C11 C16 C15 178.8(3) . . . . ?
Zn1 O4 C9 O3 8.4(4) 1_565 . . . ?
Zn1 O4 C9 C6 -170.1(2) 1_565 . . . ?
C5 C6 C9 O3 174.2(3) . . . . ?
C7 C6 C9 O3 -8.2(4) . . . . ?
C5 C6 C9 O4 -7.3(4) . . . . ?
C7 C6 C9 O4 170.3(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
O6 H6A O9 0.90(2) 2.15(2) 3.041(4) 169(5) 2_666
O6 H6B O2 0.90(2) 2.09(2) 2.970(4) 164(5) 2_766
O7 H7A O1 0.901(19) 2.16(3) 3.014(3) 159(5) 2_666
O7 H7B O9 0.89(2) 2.17(2) 3.056(4) 177(5) 1_655
N1 H1N O8 0.80(4) 2.16(4) 2.950(4) 170(3) 2_666
O9 H9B O5 0.889(19) 1.91(2) 2.786(4) 169(4) 1_544
O8 H8B O3 0.873(19) 1.93(2) 2.784(4) 165(4) 1_545
O8 H8A O3 0.886(19) 1.96(2) 2.848(4) 174(4) 2_766
O9 H9A O8 0.877(19) 2.36(2) 3.190(5) 158(4) 1_455

_refine_diff_density_max         0.468
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.094

_shelxl_version_number           2014-3

