# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_1-152
_database_code_depnum_ccdc_archive 'CCDC 1526162'
_audit_update_record             
;
2017-01-09 deposited with the CCDC.
2017-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_absolute_configuration rm
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 O6 Zn'
_chemical_formula_sum            'C16 H14 O6 Zn'
_chemical_formula_weight         367.64

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   5.7071(11)
_cell_length_b                   7.8905(16)
_cell_length_c                   15.868(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.78(3)
_cell_angle_gamma                90.00
_cell_volume                     708.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6557
_cell_measurement_theta_min      3.60
_cell_measurement_theta_max      27.52

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
_exptl_absorpt_coefficient_mu    1.765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4255
_exptl_absorpt_correction_T_max  0.5380
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scan'
_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            6910
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0581
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.60
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3103
_reflns_number_gt                2739
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXL-97

_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)+(0.0597P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.000(18)
_refine_ls_number_reflns         3103
_refine_ls_number_parameters     209
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.1064
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_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
C1 C -0.0563(6) 0.9114(8) 0.78154(19) 0.0278(6) Uani 1 1 d . . .
C2 C 0.1465(8) 0.8182(5) 0.8034(2) 0.0333(9) Uani 1 1 d . . .
H2 H 0.2070 0.7543 0.7620 0.040 Uiso 1 1 calc R . .
C3 C 0.2613(7) 0.8180(6) 0.8855(2) 0.0311(9) Uani 1 1 d . . .
H3 H 0.3988 0.7544 0.8982 0.037 Uiso 1 1 calc R . .
C4 C 0.1772(5) 0.9106(7) 0.95003(19) 0.0242(6) Uani 1 1 d . . .
C5 C -0.0283(7) 1.0046(6) 0.9265(2) 0.0303(9) Uani 1 1 d . . .
H5 H -0.0886 1.0692 0.9675 0.036 Uiso 1 1 calc R . .
C6 C -0.1459(8) 1.0053(6) 0.8440(2) 0.0325(9) Uani 1 1 d . . .
H6 H -0.2838 1.0681 0.8306 0.039 Uiso 1 1 calc R . .
C7 C 0.3051(5) 0.9134(7) 1.03847(19) 0.0240(6) Uani 1 1 d . . .
C8 C 0.5225(7) 0.8330(6) 1.0592(3) 0.0336(9) Uani 1 1 d . . .
H8 H 0.5887 0.7759 1.0168 0.040 Uiso 1 1 calc R . .
C9 C 0.6429(7) 0.8356(6) 1.1409(3) 0.0347(9) Uani 1 1 d . . .
H9 H 0.7883 0.7812 1.1524 0.042 Uiso 1 1 calc R . .
C10 C 0.5501(5) 0.9180(8) 1.20583(19) 0.0251(6) Uani 1 1 d . . .
C11 C 0.3336(7) 1.0000(6) 1.1863(2) 0.0313(9) Uani 1 1 d . . .
H11 H 0.2697 1.0590 1.2285 0.038 Uiso 1 1 calc R . .
C12 C 0.2132(7) 0.9948(6) 1.1051(2) 0.0320(9) Uani 1 1 d . . .
H12 H 0.0660 1.0469 1.0942 0.038 Uiso 1 1 calc R . .
C13 C -0.1825(6) 1.0553(5) 0.5706(2) 0.0222(7) Uani 1 1 d . . .
C14 C -0.2714(7) 1.0439(5) 0.6569(2) 0.0249(7) Uani 1 1 d . . .
H14 H -0.2277 1.1460 0.6905 0.030 Uiso 1 1 calc R . .
C15 C -0.5384(8) 1.0216(7) 0.6430(3) 0.0475(12) Uani 1 1 d . . .
H15A H -0.5771 0.9129 0.6177 0.071 Uiso 1 1 calc R . .
H15B H -0.6088 1.1092 0.6059 0.071 Uiso 1 1 calc R . .
H15C H -0.5979 1.0286 0.6967 0.071 Uiso 1 1 calc R . .
C16 C 0.6891(6) 0.9261(7) 1.2922(2) 0.0282(7) Uani 1 1 d . . .
Zn1 Zn -0.01340(6) 0.91559(6) 0.42657(2) 0.02537(13) Uani 1 1 d . . .
O1 O -0.1536(6) 1.1959(3) 0.53775(18) 0.0337(7) Uani 1 1 d . . .
O2 O -0.1491(4) 0.9160(5) 0.53445(14) 0.0305(5) Uani 1 1 d . . .
O3 O -0.1625(5) 0.8964(4) 0.69885(15) 0.0383(7) Uani 1 1 d . . .
O4 O 0.6146(6) 1.0064(5) 1.35163(19) 0.0427(8) Uani 1 1 d . . .
O5 O 0.8880(5) 0.8552(4) 1.30478(19) 0.0402(8) Uani 1 1 d . . .
O6 O 0.2364(5) 1.0860(4) 0.4248(2) 0.0364(7) Uani 1 1 d . . .
H61 H 0.3492 1.0763 0.3948 0.055 Uiso 1 1 d R . .
H62 H 0.2083 1.1878 0.4369 0.055 Uiso 1 1 d R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O3 1.374(4) . ?
C1 C2 1.376(6) . ?
C1 C6 1.389(6) . ?
C2 C3 1.377(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.395(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.395(6) . ?
C4 C7 1.492(4) . ?
C5 C6 1.387(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.392(6) . ?
C7 C12 1.398(5) . ?
C8 C9 1.383(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.383(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.392(5) . ?
C10 C16 1.489(4) . ?
C11 C12 1.376(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 O1 1.246(5) . ?
C13 O2 1.267(5) . ?
C13 C14 1.525(5) . ?
C14 O3 1.440(5) . ?
C14 C15 1.520(6) . ?
C14 H14 0.9800 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 O4 1.257(5) . ?
C16 O5 1.257(5) . ?
C16 Zn1 2.541(3) 1_656 ?
Zn1 O6 1.963(3) . ?
Zn1 O2 1.972(2) . ?
Zn1 O5 1.996(3) 1_454 ?
Zn1 O1 2.022(3) 2_546 ?
Zn1 O4 2.398(3) 1_454 ?
Zn1 C16 2.541(3) 1_454 ?
O1 Zn1 2.022(3) 2_556 ?
O4 Zn1 2.398(3) 1_656 ?
O5 Zn1 1.996(3) 1_656 ?
O6 H61 0.8540 . ?
O6 H62 0.8459 . ?

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 C1 C2 116.2(4) . . ?
O3 C1 C6 124.7(4) . . ?
C2 C1 C6 119.0(3) . . ?
C1 C2 C3 121.0(4) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 121.8(4) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 116.2(3) . . ?
C5 C4 C7 122.1(4) . . ?
C3 C4 C7 121.7(4) . . ?
C6 C5 C4 122.5(4) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C5 C6 C1 119.5(4) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C8 C7 C12 116.4(3) . . ?
C8 C7 C4 121.5(4) . . ?
C12 C7 C4 122.1(3) . . ?
C9 C8 C7 121.8(4) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C10 C9 C8 120.9(4) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 118.1(3) . . ?
C9 C10 C16 119.7(4) . . ?
C11 C10 C16 122.1(4) . . ?
C12 C11 C10 120.7(4) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 122.0(4) . . ?
C11 C12 H12 119.0 . . ?
C7 C12 H12 119.0 . . ?
O1 C13 O2 123.1(3) . . ?
O1 C13 C14 120.5(3) . . ?
O2 C13 C14 116.3(3) . . ?
O3 C14 C15 109.5(4) . . ?
O3 C14 C13 106.7(3) . . ?
C15 C14 C13 109.0(3) . . ?
O3 C14 H14 110.5 . . ?
C15 C14 H14 110.5 . . ?
C13 C14 H14 110.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 O5 119.6(3) . . ?
O4 C16 C10 121.3(4) . . ?
O5 C16 C10 119.0(4) . . ?
O4 C16 Zn1 69.02(19) . 1_656 ?
O5 C16 Zn1 50.62(17) . 1_656 ?
C10 C16 Zn1 169.5(3) . 1_656 ?
O6 Zn1 O2 112.52(13) . . ?
O6 Zn1 O5 105.04(14) . 1_454 ?
O2 Zn1 O5 138.45(12) . 1_454 ?
O6 Zn1 O1 106.01(14) . 2_546 ?
O2 Zn1 O1 89.07(13) . 2_546 ?
O5 Zn1 O1 97.29(12) 1_454 2_546 ?
O6 Zn1 O4 112.59(13) . 1_454 ?
O2 Zn1 O4 90.26(11) . 1_454 ?
O5 Zn1 O4 58.44(11) 1_454 1_454 ?
O1 Zn1 O4 138.33(13) 2_546 1_454 ?
O6 Zn1 C16 111.69(14) . 1_454 ?
O2 Zn1 C16 115.60(11) . 1_454 ?
O5 Zn1 C16 29.13(13) 1_454 1_454 ?
O1 Zn1 C16 119.94(15) 2_546 1_454 ?
O4 Zn1 C16 29.31(12) 1_454 1_454 ?
C13 O1 Zn1 136.9(3) . 2_556 ?
C13 O2 Zn1 119.7(3) . . ?
C1 O3 C14 118.6(4) . . ?
C16 O4 Zn1 81.7(2) . 1_656 ?
C16 O5 Zn1 100.2(2) . 1_656 ?
Zn1 O6 H61 123.4 . . ?
Zn1 O6 H62 119.1 . . ?
H61 O6 H62 113.0 . . ?

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 H61 O4 0.85 1.83 2.661(4) 163.7 1_554
O6 H62 O2 0.85 1.90 2.744(5) 179.1 2_556

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.096
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2-229
_database_code_depnum_ccdc_archive 'CCDC 1526163'
_audit_update_record             
;
2017-01-09 deposited with the CCDC.
2017-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_absolute_configuration rm
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 O6 Zn'
_chemical_formula_sum            'C16 H14 O6 Zn'
_chemical_formula_weight         367.64

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   5.6961(11)
_cell_length_b                   7.8959(16)
_cell_length_c                   15.870(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.98(3)
_cell_angle_gamma                90.00
_cell_volume                     706.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6240
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      27.59

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
_exptl_absorpt_coefficient_mu    1.768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5493
_exptl_absorpt_correction_T_max  0.6337
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scan'
_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            5257
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0450
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.61
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2414
_reflns_number_gt                2268
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXL-97

_refine_special_details          
; 
omit    -4   1   5
omit    -4  -1   5
omit -2 50
 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)+(0.0319P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.013(13)
_refine_ls_number_reflns         2414
_refine_ls_number_parameters     209
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0627
_refine_ls_wR_factor_gt          0.0609
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0554(5) 0.0885(6) 0.21842(16) 0.0248(6) Uani 1 1 d . . .
C2 C 0.8532(6) 0.1830(4) 0.1966(2) 0.0304(8) Uani 1 1 d . . .
H2 H 0.7940 0.2483 0.2376 0.036 Uiso 1 1 calc R . .
C3 C 0.7380(7) 0.1815(4) 0.1145(2) 0.0294(7) Uani 1 1 d . . .
H3 H 0.6003 0.2449 0.1014 0.035 Uiso 1 1 calc R . .
C4 C 0.8218(5) 0.0872(6) 0.05000(16) 0.0222(5) Uani 1 1 d . . .
C5 C 1.0285(6) -0.0049(4) 0.07360(19) 0.0277(7) Uani 1 1 d . . .
H5 H 1.0907 -0.0679 0.0324 0.033 Uiso 1 1 calc R . .
C6 C 1.1452(6) -0.0062(4) 0.1560(2) 0.0299(7) Uani 1 1 d . . .
H6 H 1.2825 -0.0699 0.1697 0.036 Uiso 1 1 calc R . .
C7 C 0.6948(5) 0.0867(6) -0.03838(15) 0.0208(5) Uani 1 1 d . . .
C8 C 0.4779(6) 0.1683(5) -0.0592(2) 0.0322(8) Uani 1 1 d . . .
H8 H 0.4123 0.2262 -0.0171 0.039 Uiso 1 1 calc R . .
C9 C 0.3579(6) 0.1654(4) -0.1410(2) 0.0312(8) Uani 1 1 d . . .
H9 H 0.2131 0.2209 -0.1529 0.037 Uiso 1 1 calc R . .
C10 C 0.4500(5) 0.0809(6) -0.20573(16) 0.0217(5) Uani 1 1 d . . .
C11 C 0.6667(6) 0.0000(4) -0.1865(2) 0.0292(7) Uani 1 1 d . . .
H11 H 0.7316 -0.0572 -0.2290 0.035 Uiso 1 1 calc R . .
C12 C 0.7868(6) 0.0036(4) -0.1050(2) 0.0278(7) Uani 1 1 d . . .
H12 H 0.9328 -0.0504 -0.0937 0.033 Uiso 1 1 calc R . .
C13 C 1.1812(5) -0.0542(3) 0.42892(18) 0.0183(6) Uani 1 1 d . . .
C14 C 1.2729(6) -0.0440(3) 0.34337(19) 0.0216(7) Uani 1 1 d . . .
H14 H 1.2290 -0.1463 0.3099 0.026 Uiso 1 1 calc R . .
C15 C 1.5375(7) -0.0231(5) 0.3575(3) 0.0413(9) Uani 1 1 d . . .
H15A H 1.5773 0.0836 0.3848 0.062 Uiso 1 1 calc R . .
H15B H 1.5967 -0.0262 0.3038 0.062 Uiso 1 1 calc R . .
H15C H 1.6076 -0.1133 0.3930 0.062 Uiso 1 1 calc R . .
C16 C 0.3115(5) 0.0726(5) -0.29201(18) 0.0256(6) Uani 1 1 d . . .
Zn1 Zn 1.01332(6) 0.08447(5) 0.573396(17) 0.02221(11) Uani 1 1 d . . .
O1 O 1.1535(5) -0.1956(2) 0.46201(14) 0.0292(6) Uani 1 1 d . . .
O2 O 1.1481(3) 0.0831(4) 0.46551(11) 0.0273(4) Uani 1 1 d . . .
O3 O 1.1615(4) 0.1030(3) 0.30094(13) 0.0355(6) Uani 1 1 d . . .
O4 O 0.3849(5) -0.0069(3) -0.35172(15) 0.0409(6) Uani 1 1 d . . .
O5 O 0.1129(4) 0.1453(3) -0.30503(16) 0.0366(6) Uani 1 1 d . . .
O6 O 0.7641(4) -0.0858(3) 0.57524(16) 0.0342(6) Uani 1 1 d . . .
H61 H 0.6513 -0.0761 0.6052 0.051 Uiso 1 1 d R . .
H62 H 0.7922 -0.1875 0.5632 0.051 Uiso 1 1 d R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O3 1.369(3) . ?
C1 C2 1.375(5) . ?
C1 C6 1.394(5) . ?
C2 C3 1.374(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.402(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(5) . ?
C4 C7 1.486(4) . ?
C5 C6 1.382(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.393(5) . ?
C7 C12 1.406(4) . ?
C8 C9 1.381(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.387(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.386(5) . ?
C10 C16 1.484(4) . ?
C11 C12 1.377(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 O1 1.253(3) . ?
C13 O2 1.257(4) . ?
C13 C14 1.523(4) . ?
C14 O3 1.444(4) . ?
C14 C15 1.502(5) . ?
C14 H14 0.9800 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 O4 1.256(4) . ?
C16 O5 1.259(4) . ?
C16 Zn1 2.539(3) 1_454 ?
Zn1 O6 1.958(2) . ?
Zn1 O2 1.9713(17) . ?
Zn1 O5 1.993(2) 1_656 ?
Zn1 O1 2.021(2) 2_756 ?
Zn1 O4 2.390(3) 1_656 ?
Zn1 C16 2.539(3) 1_656 ?
O1 Zn1 2.021(2) 2_746 ?
O4 Zn1 2.390(3) 1_454 ?
O5 Zn1 1.993(2) 1_454 ?
O6 H61 0.8543 . ?
O6 H62 0.8465 . ?

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 C1 C2 116.0(3) . . ?
O3 C1 C6 124.6(3) . . ?
C2 C1 C6 119.3(3) . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 122.0(3) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 116.2(3) . . ?
C5 C4 C7 122.4(3) . . ?
C3 C4 C7 121.4(3) . . ?
C6 C5 C4 122.5(3) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C8 C7 C12 116.6(3) . . ?
C8 C7 C4 121.5(3) . . ?
C12 C7 C4 121.9(3) . . ?
C9 C8 C7 121.5(3) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 121.0(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 118.4(3) . . ?
C11 C10 C16 121.7(3) . . ?
C9 C10 C16 119.8(3) . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 121.9(3) . . ?
C11 C12 H12 119.1 . . ?
C7 C12 H12 119.1 . . ?
O1 C13 O2 122.7(3) . . ?
O1 C13 C14 120.0(2) . . ?
O2 C13 C14 117.3(2) . . ?
O3 C14 C15 110.4(3) . . ?
O3 C14 C13 106.0(2) . . ?
C15 C14 C13 109.5(3) . . ?
O3 C14 H14 110.3 . . ?
C15 C14 H14 110.3 . . ?
C13 C14 H14 110.3 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 O5 119.3(3) . . ?
O4 C16 C10 121.9(3) . . ?
O5 C16 C10 118.8(3) . . ?
O4 C16 Zn1 68.74(18) . 1_454 ?
O5 C16 Zn1 50.55(15) . 1_454 ?
C10 C16 Zn1 169.2(2) . 1_454 ?
O6 Zn1 O2 112.32(11) . . ?
O6 Zn1 O5 105.09(11) . 1_656 ?
O2 Zn1 O5 138.54(10) . 1_656 ?
O6 Zn1 O1 106.26(11) . 2_756 ?
O2 Zn1 O1 89.32(10) . 2_756 ?
O5 Zn1 O1 97.00(9) 1_656 2_756 ?
O6 Zn1 O4 112.27(10) . 1_656 ?
O2 Zn1 O4 90.31(9) . 1_656 ?
O5 Zn1 O4 58.53(9) 1_656 1_656 ?
O1 Zn1 O4 138.35(10) 2_756 1_656 ?
O6 Zn1 C16 111.33(11) . 1_656 ?
O2 Zn1 C16 115.76(9) . 1_656 ?
O5 Zn1 C16 29.21(10) 1_656 1_656 ?
O1 Zn1 C16 119.95(11) 2_756 1_656 ?
O4 Zn1 C16 29.31(10) 1_656 1_656 ?
C13 O1 Zn1 136.9(2) . 2_746 ?
C13 O2 Zn1 120.5(2) . . ?
C1 O3 C14 119.1(3) . . ?
C16 O4 Zn1 81.95(19) . 1_454 ?
C16 O5 Zn1 100.2(2) . 1_454 ?
Zn1 O6 H61 123.4 . . ?
Zn1 O6 H62 119.2 . . ?
H61 O6 H62 113.1 . . ?

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 H61 O4 0.85 1.83 2.664(4) 163.8 1_556
O6 H62 O2 0.85 1.91 2.756(4) 179.1 2_746

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.069
####################################################################### 
# 
# 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_3-209
_database_code_depnum_ccdc_archive 'CCDC 1526164'
_audit_update_record             
;
2017-01-09 deposited with the CCDC.
2017-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_absolute_configuration rm
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 O7 Zn'
_chemical_formula_sum            'C14 H14 O7 Zn'
_chemical_formula_weight         359.62

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'
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'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   6.0565(12)
_cell_length_b                   7.3687(15)
_cell_length_c                   15.825(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.60(3)
_cell_angle_gamma                90.00
_cell_volume                     701.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6501
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      27.69

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    1.784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6397
_exptl_absorpt_correction_T_max  0.6907
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scan'
_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            6577
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2802
_reflns_number_gt                2666
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXL-97

_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)+(0.0233P)²+0.0754P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.020(10)
_refine_ls_number_reflns         2802
_refine_ls_number_parameters     200
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0575
_refine_ls_wR_factor_gt          0.0567
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.087
_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
C1 C 0.3263(3) 0.7496(3) 0.54705(13) 0.0223(4) Uani 1 1 d . . .
C2 C 0.4035(4) 0.7131(3) 0.63353(14) 0.0258(5) Uani 1 1 d . . .
H2 H 0.5438 0.6635 0.6483 0.031 Uiso 1 1 calc R . .
C3 C 0.2689(4) 0.7517(3) 0.69461(14) 0.0279(5) Uani 1 1 d . . .
C4 C 0.0559(4) 0.8260(4) 0.67495(15) 0.0316(5) Uani 1 1 d . . .
H4 H -0.0319 0.8507 0.7181 0.038 Uiso 1 1 calc R . .
C5 C -0.0215(4) 0.8619(4) 0.59234(15) 0.0300(5) Uani 1 1 d . . .
H5 H -0.1622 0.9120 0.5792 0.036 Uiso 1 1 calc R . .
C6 C 0.1103(4) 0.8234(3) 0.52659(13) 0.0227(4) Uani 1 1 d . . .
C7 C 0.0295(4) 0.8549(3) 0.44025(14) 0.0252(5) Uani 1 1 d . . .
H7 H -0.1145 0.8978 0.4263 0.030 Uiso 1 1 calc R . .
C8 C 0.1611(4) 0.8227(3) 0.37744(14) 0.0261(5) Uani 1 1 d . . .
C9 C 0.3803(4) 0.7554(4) 0.39789(15) 0.0299(5) Uani 1 1 d . . .
H9 H 0.4716 0.7385 0.3552 0.036 Uiso 1 1 calc R . .
C10 C 0.4566(3) 0.7157(4) 0.47986(15) 0.0281(5) Uani 1 1 d . . .
H10 H 0.5974 0.6652 0.4922 0.034 Uiso 1 1 calc R . .
C11 C 0.0677(4) 0.8649(4) 0.28758(15) 0.0339(6) Uani 1 1 d . . .
C12 C 0.3606(4) 0.8550(4) 0.83837(15) 0.0294(5) Uani 1 1 d . . .
H12 H 0.2901 0.9630 0.8110 0.035 Uiso 1 1 calc R . .
C13 C 0.2399(4) 0.8023(3) 0.91407(15) 0.0291(5) Uani 1 1 d . . .
C14 C 0.6042(5) 0.8936(5) 0.8647(2) 0.0567(10) Uani 1 1 d . . .
H14A H 0.6761 0.7854 0.8877 0.085 Uiso 1 1 calc R . .
H14B H 0.6183 0.9874 0.9071 0.085 Uiso 1 1 calc R . .
H14C H 0.6728 0.9325 0.8160 0.085 Uiso 1 1 calc R . .
O1 O 0.3426(3) 0.7062(2) 0.77864(10) 0.0351(4) Uani 1 1 d . . .
O2 O 0.1645(4) 0.6452(3) 0.92023(15) 0.0424(5) Uani 1 1 d . . .
O3 O 0.2244(3) 0.9202(3) 0.96909(10) 0.0396(4) Uani 1 1 d . . .
O4 O -0.1380(3) 0.8456(3) 0.26772(11) 0.0394(4) Uani 1 1 d . . .
O5 O 0.1871(3) 0.9309(6) 0.23727(11) 0.0599(5) Uani 1 1 d . . .
O6 O 0.5303(3) 0.3660(3) 0.87313(12) 0.0440(5) Uani 1 1 d . . .
H61 H 0.5892 0.4001 0.9219 0.066 Uiso 1 1 d R . .
H62 H 0.6189 0.3840 0.8360 0.066 Uiso 1 1 d R . .
O7 O 0.0968(4) 0.2672(3) 0.92958(14) 0.0465(6) Uani 1 1 d . . .
H71 H 0.0067 0.2973 0.9646 0.070 Uiso 1 1 d R . .
H72 H 0.1470 0.1602 0.9378 0.070 Uiso 1 1 d R . .
Zn1 Zn 0.21384(3) 0.43869(4) 0.846270(13) 0.02647(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
C1 C10 1.417(3) . ?
C1 C6 1.419(3) . ?
C1 C2 1.420(3) . ?
C2 C3 1.364(3) . ?
C2 H2 0.9300 . ?
C3 O1 1.394(3) . ?
C3 C4 1.403(3) . ?
C4 C5 1.363(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.411(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.416(3) . ?
C7 C8 1.364(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.419(3) . ?
C8 C11 1.501(3) . ?
C9 C10 1.358(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 O5 1.235(3) . ?
C11 O4 1.257(3) . ?
C12 O1 1.444(3) . ?
C12 C14 1.514(4) . ?
C12 C13 1.524(3) . ?
C12 H12 0.9800 . ?
C13 O3 1.241(3) . ?
C13 O2 1.252(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O1 Zn1 2.4146(18) . ?
O2 Zn1 1.964(2) . ?
O4 Zn1 1.9354(18) 2_556 ?
O6 Zn1 1.9884(18) . ?
O6 H61 0.8499 . ?
O6 H62 0.8500 . ?
O7 Zn1 2.013(2) . ?
O7 H71 0.8499 . ?
O7 H72 0.8500 . ?
Zn1 O4 1.9354(18) 2_546 ?

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
C10 C1 C6 118.34(19) . . ?
C10 C1 C2 122.6(2) . . ?
C6 C1 C2 119.03(19) . . ?
C3 C2 C1 119.1(2) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 O1 118.3(2) . . ?
C2 C3 C4 122.2(2) . . ?
O1 C3 C4 119.4(2) . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C7 121.1(2) . . ?
C5 C6 C1 119.6(2) . . ?
C7 C6 C1 119.34(19) . . ?
C8 C7 C6 120.5(2) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.3(2) . . ?
C7 C8 C11 117.8(2) . . ?
C9 C8 C11 121.9(2) . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C1 121.4(2) . . ?
C9 C10 H10 119.3 . . ?
C1 C10 H10 119.3 . . ?
O5 C11 O4 121.3(2) . . ?
O5 C11 C8 120.5(2) . . ?
O4 C11 C8 117.9(2) . . ?
O1 C12 C14 108.7(2) . . ?
O1 C12 C13 108.3(2) . . ?
C14 C12 C13 111.8(2) . . ?
O1 C12 H12 109.3 . . ?
C14 C12 H12 109.3 . . ?
C13 C12 H12 109.3 . . ?
O3 C13 O2 122.3(2) . . ?
O3 C13 C12 117.1(2) . . ?
O2 C13 C12 120.6(2) . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 O1 C12 115.68(19) . . ?
C3 O1 Zn1 122.35(15) . . ?
C12 O1 Zn1 109.50(13) . . ?
C13 O2 Zn1 126.03(17) . . ?
C11 O4 Zn1 108.36(16) . 2_556 ?
Zn1 O6 H61 114.1 . . ?
Zn1 O6 H62 118.7 . . ?
H61 O6 H62 110.4 . . ?
Zn1 O7 H71 124.3 . . ?
Zn1 O7 H72 122.4 . . ?
H71 O7 H72 112.8 . . ?
O4 Zn1 O2 142.59(10) 2_546 . ?
O4 Zn1 O6 102.92(8) 2_546 . ?
O2 Zn1 O6 106.87(10) . . ?
O4 Zn1 O7 108.91(10) 2_546 . ?
O2 Zn1 O7 90.40(9) . . ?
O6 Zn1 O7 95.41(9) . . ?
O4 Zn1 O1 86.01(7) 2_546 . ?
O2 Zn1 O1 73.17(8) . . ?
O6 Zn1 O1 87.83(7) . . ?
O7 Zn1 O1 163.47(8) . . ?

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 H61 O3 0.85 1.96 2.784(3) 164.3 2_647
O6 H62 O5 0.85 1.78 2.626(3) 176.6 2_646
O7 H71 O3 0.85 2.05 2.888(3) 166.8 2_547
O7 H71 O2 0.85 2.47 3.135(3) 135.9 2_547
O7 H72 O3 0.85 1.88 2.723(3) 170.6 1_545

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.062
####################################################################### 
# 
# 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_4-708
_database_code_depnum_ccdc_archive 'CCDC 1526165'
_audit_update_record             
;
2017-01-09 deposited with the CCDC.
2017-03-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 O7 Zn'
_chemical_formula_sum            'C14 H14 O7 Zn'
_chemical_formula_weight         359.64

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'
_symmetry_space_group_name_Hall  'P 2yb '

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

_cell_length_a                   6.045(5)
_cell_length_b                   7.363(5)
_cell_length_c                   15.846(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 96.636(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     700.6(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1193
_cell_measurement_theta_min      3.0483
_cell_measurement_theta_max      29.6388

_exptl_crystal_description       strip
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368.0
_exptl_absorpt_coefficient_mu    1.786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.644
_exptl_absorpt_correction_T_max  0.793
_exptl_absorpt_process_details   sadabs(Sheldrick,1996)

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_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            2471
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2464
_reflns_number_gt                1812
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0924P)²+0.4804P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(3)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2464
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1271
_refine_ls_wR_factor_gt          0.1247
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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
C1 C 0.2696(10) 0.2327(9) 1.1941(3) 0.0257(13) Uani 1 1 d . . .
C2 C 0.0550(10) 0.1587(10) 1.1752(4) 0.0291(14) Uani 1 1 d . . .
H2 H -0.0332 0.1355 1.2184 0.035 Uiso 1 1 calc R . .
C3 C -0.0221(10) 0.1213(10) 1.0922(4) 0.0284(14) Uani 1 1 d . . .
H3 H -0.1622 0.0697 1.0789 0.034 Uiso 1 1 calc R . .
C4 C 0.1103(9) 0.1608(8) 1.0268(3) 0.0206(12) Uani 1 1 d . . .
C5 C 0.3269(9) 0.2338(8) 1.0473(3) 0.0199(11) Uani 1 1 d . . .
C6 C 0.4033(10) 0.2716(9) 1.1329(3) 0.0246(13) Uani 1 1 d . . .
H6 H 0.5434 0.3224 1.1475 0.029 Uiso 1 1 calc R . .
C7 C 0.4577(10) 0.2686(10) 0.9798(4) 0.0291(14) Uani 1 1 d . . .
H7 H 0.5985 0.3199 0.9918 0.035 Uiso 1 1 calc R . .
C8 C 0.3793(10) 0.2277(10) 0.8976(4) 0.0262(13) Uani 1 1 d . . .
H8 H 0.4700 0.2444 0.8547 0.031 Uiso 1 1 calc R . .
C9 C 0.1606(10) 0.1602(9) 0.8778(3) 0.0246(13) Uani 1 1 d . . .
C10 C 0.0311(10) 0.1292(9) 0.9404(3) 0.0244(13) Uani 1 1 d . . .
H10 H -0.1132 0.0861 0.9264 0.029 Uiso 1 1 calc R . .
C11 C 0.0699(11) 0.1181(10) 0.7879(4) 0.0308(14) Uani 1 1 d . . .
C12 C -0.3610(11) -0.3713(10) 0.6611(3) 0.0289(13) Uani 1 1 d . . .
H12 H -0.2912 -0.4798 0.6883 0.035 Uiso 1 1 calc R . .
C13 C -0.2397(11) -0.3185(9) 0.5857(4) 0.0258(14) Uani 1 1 d . . .
C14 C -0.6030(13) -0.4084(13) 0.6345(5) 0.056(3) Uani 1 1 d . . .
H14A H -0.6743 -0.4411 0.6835 0.084 Uiso 1 1 calc R . .
H14B H -0.6174 -0.5064 0.5943 0.084 Uiso 1 1 calc R . .
H14C H -0.6723 -0.3015 0.6088 0.084 Uiso 1 1 calc R . .
O1 O 0.1873(8) 0.0497(15) 0.7369(3) 0.0581(14) Uani 1 1 d . . .
O2 O -0.1371(8) 0.1376(8) 0.7683(3) 0.0365(11) Uani 1 1 d . . .
O3 O -0.5298(8) 0.1168(8) 0.6262(3) 0.0398(13) Uani 1 1 d . . .
H310 H -0.6370 0.1877 0.6095 0.048 Uiso 1 1 d R . .
H320 H -0.5725 0.0481 0.6643 0.048 Uiso 1 1 d R . .
O4 O -0.0938(10) 0.2182(8) 0.5713(4) 0.0466(15) Uani 1 1 d . . .
H410 H -0.1514 0.1537 0.5300 0.056 Uiso 1 1 d R . .
H420 H -0.1038 0.3287 0.5558 0.056 Uiso 1 1 d R . .
O5 O -0.3426(8) -0.2224(6) 0.7211(2) 0.0329(11) Uani 1 1 d . . .
O6 O -0.1642(10) -0.1613(8) 0.5793(4) 0.0402(13) Uani 1 1 d . . .
O7 O -0.2247(8) -0.4354(8) 0.5307(2) 0.0398(11) Uani 1 1 d . . .
Zn1 Zn -0.21390(9) 0.04551(11) 0.65377(3) 0.0247(2) 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
C1 C6 1.362(8) . ?
C1 O5 1.404(7) 2_557 ?
C1 C2 1.407(9) . ?
C2 C3 1.373(8) . ?
C3 C4 1.410(8) . ?
C4 C10 1.417(7) . ?
C4 C5 1.418(8) . ?
C5 C6 1.410(8) . ?
C5 C7 1.425(8) . ?
C7 C8 1.367(8) . ?
C8 C9 1.413(9) . ?
C9 C10 1.352(8) . ?
C9 C11 1.498(8) . ?
C11 O1 1.243(8) . ?
C11 O2 1.262(8) . ?
C12 O5 1.448(8) . ?
C12 C14 1.500(10) . ?
C12 C13 1.523(8) . ?
C13 O7 1.235(8) . ?
C13 O6 1.253(9) . ?
O2 Zn1 1.942(4) . ?
O3 Zn1 1.980(5) . ?
O4 Zn1 2.017(5) . ?
O5 C1 1.404(7) 2_547 ?
O5 Zn1 2.414(5) . ?
O6 Zn1 1.970(6) . ?

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
C6 C1 O5 119.0(5) . 2_557 ?
C6 C1 C2 122.6(5) . . ?
O5 C1 C2 118.4(5) 2_557 . ?
C3 C2 C1 119.0(5) . . ?
C2 C3 C4 120.3(6) . . ?
C3 C4 C10 121.3(5) . . ?
C3 C4 C5 119.9(5) . . ?
C10 C4 C5 118.9(5) . . ?
C6 C5 C4 119.0(5) . . ?
C6 C5 C7 122.6(5) . . ?
C4 C5 C7 118.4(5) . . ?
C1 C6 C5 119.2(5) . . ?
C8 C7 C5 120.9(6) . . ?
C7 C8 C9 120.1(5) . . ?
C10 C9 C8 120.2(5) . . ?
C10 C9 C11 118.9(6) . . ?
C8 C9 C11 120.9(5) . . ?
C9 C10 C4 121.4(6) . . ?
O1 C11 O2 120.6(6) . . ?
O1 C11 C9 121.9(6) . . ?
O2 C11 C9 117.1(5) . . ?
O5 C12 C14 108.7(6) . . ?
O5 C12 C13 108.4(6) . . ?
C14 C12 C13 111.7(5) . . ?
O7 C13 O6 122.0(6) . . ?
O7 C13 C12 117.1(6) . . ?
O6 C13 C12 120.8(6) . . ?
C11 O2 Zn1 108.3(4) . . ?
C1 O5 C12 116.3(5) 2_547 . ?
C1 O5 Zn1 122.2(4) 2_547 . ?
C12 O5 Zn1 109.4(3) . . ?
C13 O6 Zn1 125.7(4) . . ?
O2 Zn1 O6 142.4(3) . . ?
O2 Zn1 O3 103.5(2) . . ?
O6 Zn1 O3 106.4(2) . . ?
O2 Zn1 O4 108.7(3) . . ?
O6 Zn1 O4 90.5(2) . . ?
O3 Zn1 O4 95.8(2) . . ?
O2 Zn1 O5 85.79(18) . . ?
O6 Zn1 O5 73.3(2) . . ?
O3 Zn1 O5 87.8(2) . . ?
O4 Zn1 O5 163.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.826
_refine_diff_density_rms         0.113
