# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1479165'
_audit_update_record             
;
2016-05-10 deposited with the CCDC.
2016-11-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 N O10 Zn2'
_chemical_formula_weight         485.03

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   P21/c

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

_cell_length_a                   10.997(2)
_cell_length_b                   14.914(3)
_cell_length_c                   14.368(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.31(3)
_cell_angle_gamma                90.00
_cell_volume                     2224.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    17674
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.8

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             972
_exptl_absorpt_coefficient_mu    2.20
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  SCX-MINI
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19009
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3911
_reflns_number_gt                3398
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0571P)²+9.0115P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3911
_refine_ls_number_parameters     256
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1336
_refine_ls_wR_factor_gt          0.1282
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.116
_refine_ls_shift/su_mean         0.006

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
O8 O 0.9082(3) 0.1419(3) 0.1963(3) 0.0347(9) Uani 1 1 d . . .
O10 O 0.5663(4) 0.3722(3) 0.3698(3) 0.0361(9) Uani 1 1 d . . .
Zn1 Zn 0.62034(5) 0.02999(4) -0.03366(4) 0.01865(17) Uani 1 1 d . . .
Zn2 Zn 0.07237(6) 0.15007(4) 0.16101(5) 0.0324(2) Uani 1 1 d . . .
O1 O 0.5326(3) 0.0562(2) 0.0689(2) 0.0236(8) Uani 1 1 d . . .
C2 C 0.4650(4) 0.1615(3) 0.1643(4) 0.0210(10) Uani 1 1 d . . .
O2 O 0.2522(4) 0.1791(3) 0.1576(3) 0.0403(10) Uani 1 1 d . . .
C4 C 0.6217(5) 0.2644(3) 0.2696(4) 0.0266(11) Uani 1 1 d . . .
C1 C 0.5600(4) 0.1223(3) 0.1314(3) 0.0189(10) Uani 1 1 d . . .
C7 C 0.3269(5) 0.1336(3) 0.1288(4) 0.0231(11) Uani 1 1 d . . .
C5 C 0.7146(5) 0.2255(3) 0.2374(4) 0.0244(11) Uani 1 1 d . . .
H5 H 0.7984 0.2475 0.2614 0.029 Uiso 1 1 calc R . .
C3 C 0.4975(5) 0.2311(3) 0.2317(4) 0.0236(11) Uani 1 1 d . . .
H3 H 0.4334 0.2565 0.2523 0.028 Uiso 1 1 calc R . .
C6 C 0.6884(5) 0.1556(3) 0.1713(4) 0.0212(10) Uani 1 1 d . . .
O6 O 0.1315(4) 0.0188(3) 0.2157(3) 0.0439(10) Uani 1 1 d D . .
H6 H 0.1782 -0.0023 0.1871 0.066 Uiso 1 1 calc RD . .
O3 O 0.7804(3) 0.0660(3) 0.0731(3) 0.0408(10) Uani 1 1 d . . .
O4 O 0.7642(4) 0.3739(3) 0.3627(3) 0.0471(11) Uani 1 1 d . . .
O7 O 0.0019(4) 0.0922(3) 0.0224(3) 0.0528(12) Uani 1 1 d D . .
H7 H 0.0492 0.1049 -0.0093 0.079 Uiso 1 1 calc RD . .
O5 O 0.2878(3) 0.0692(3) 0.0718(3) 0.0447(11) Uani 1 1 d . . .
C8 C 0.7978(5) 0.1187(3) 0.1437(4) 0.0234(11) Uani 1 1 d . . .
O9 O 0.1520(5) 0.1981(3) 0.3104(3) 0.0515(12) Uani 1 1 d D . .
H9 H 0.2028 0.2389 0.3127 0.077 Uiso 1 1 calc RD . .
C9 C 0.6553(5) 0.3421(4) 0.3386(4) 0.0320(12) Uani 1 1 d . . .
N1 N 0.0212(5) 0.2818(3) 0.0973(4) 0.0410(12) Uani 1 1 d . . .
C12 C 0.0034(6) 0.4541(4) 0.0197(5) 0.0433(15) Uani 1 1 d . . .
C13 C -0.0014(8) 0.2961(5) 0.0031(6) 0.062(2) Uani 1 1 d . . .
H13 H -0.0089 0.2465 -0.0376 0.074 Uiso 1 1 calc R . .
C11 C 0.0209(10) 0.4383(5) 0.1170(6) 0.071(3) Uani 1 1 d . . .
H11 H 0.0277 0.4867 0.1593 0.086 Uiso 1 1 calc R . .
C10 C 0.0287(9) 0.3524(5) 0.1539(6) 0.070(2) Uani 1 1 d . . .
H10 H 0.0395 0.3441 0.2203 0.084 Uiso 1 1 calc R . .
C15 C -0.0145(8) 0.3800(5) -0.0396(5) 0.059(2) Uani 1 1 d . . .
H15 H -0.0352 0.3861 -0.1075 0.071 Uiso 1 1 calc R . .
H20 H 0.091(6) -0.021(2) 0.236(5) 0.071 Uiso 1 1 d D . .
H21 H -0.071(3) 0.118(5) -0.001(5) 0.071 Uiso 1 1 d D . .
H22 H 0.114(6) 0.204(4) 0.353(4) 0.071 Uiso 1 1 d 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
O8 C8 1.248(6) . ?
O8 Zn2 2.034(4) 1_655 ?
O10 C9 1.284(7) . ?
O10 Zn1 1.965(4) 4_566 ?
Zn1 O10 1.965(4) 4_565 ?
Zn1 O5 1.968(4) 3_655 ?
Zn1 O3 1.989(4) . ?
Zn1 O1 2.043(3) 3_655 ?
Zn1 O1 2.048(3) . ?
Zn2 O8 2.034(4) 1_455 ?
Zn2 O2 2.040(4) . ?
Zn2 O7 2.071(5) . ?
Zn2 O6 2.130(4) . ?
Zn2 O9 2.155(4) . ?
Zn2 N1 2.161(5) . ?
O1 C1 1.300(6) . ?
O1 Zn1 2.043(3) 3_655 ?
C2 C3 1.384(7) . ?
C2 C1 1.408(7) . ?
C2 C7 1.493(7) . ?
O2 C7 1.238(6) . ?
C4 C5 1.381(7) . ?
C4 C3 1.385(7) . ?
C4 C9 1.491(7) . ?
C1 C6 1.427(7) . ?
C7 O5 1.244(6) . ?
C5 C6 1.375(7) . ?
C6 C8 1.491(7) . ?
O3 C8 1.247(6) . ?
O4 C9 1.227(7) . ?
O5 Zn1 1.968(4) 3_655 ?
N1 C13 1.311(9) . ?
N1 C10 1.316(9) . ?
C12 C11 1.368(10) . ?
C12 C15 1.369(9) . ?
C12 C12 1.475(12) 3_565 ?
C13 C15 1.379(9) . ?
C11 C10 1.378(10) . ?

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
C8 O8 Zn2 129.1(3) . 1_655 ?
C9 O10 Zn1 114.7(3) . 4_566 ?
O10 Zn1 O5 115.15(19) 4_565 3_655 ?
O10 Zn1 O3 109.17(18) 4_565 . ?
O5 Zn1 O3 90.71(16) 3_655 . ?
O10 Zn1 O1 105.06(16) 4_565 3_655 ?
O5 Zn1 O1 85.12(14) 3_655 3_655 ?
O3 Zn1 O1 143.82(17) . 3_655 ?
O10 Zn1 O1 105.17(15) 4_565 . ?
O5 Zn1 O1 138.65(18) 3_655 . ?
O3 Zn1 O1 84.31(14) . . ?
O1 Zn1 O1 75.70(14) 3_655 . ?
O8 Zn2 O2 164.95(15) 1_455 . ?
O8 Zn2 O7 97.68(17) 1_455 . ?
O2 Zn2 O7 97.08(18) . . ?
O8 Zn2 O6 92.34(17) 1_455 . ?
O2 Zn2 O6 91.39(17) . . ?
O7 Zn2 O6 86.73(18) . . ?
O8 Zn2 O9 82.71(16) 1_455 . ?
O2 Zn2 O9 82.86(17) . . ?
O7 Zn2 O9 174.67(19) . . ?
O6 Zn2 O9 87.94(19) . . ?
O8 Zn2 N1 91.80(18) 1_455 . ?
O2 Zn2 N1 85.16(18) . . ?
O7 Zn2 N1 90.5(2) . . ?
O6 Zn2 N1 175.31(18) . . ?
O9 Zn2 N1 94.8(2) . . ?
C1 O1 Zn1 129.2(3) . 3_655 ?
C1 O1 Zn1 125.8(3) . . ?
Zn1 O1 Zn1 104.30(14) 3_655 . ?
C3 C2 C1 119.9(4) . . ?
C3 C2 C7 116.5(4) . . ?
C1 C2 C7 123.6(4) . . ?
C7 O2 Zn2 130.3(3) . . ?
C5 C4 C3 117.4(4) . . ?
C5 C4 C9 120.1(5) . . ?
C3 C4 C9 122.4(5) . . ?
O1 C1 C2 121.3(4) . . ?
O1 C1 C6 120.9(4) . . ?
C2 C1 C6 117.8(4) . . ?
O2 C7 O5 121.4(5) . . ?
O2 C7 C2 116.5(4) . . ?
O5 C7 C2 122.1(4) . . ?
C6 C5 C4 122.7(5) . . ?
C2 C3 C4 122.5(4) . . ?
C5 C6 C1 119.7(4) . . ?
C5 C6 C8 117.4(4) . . ?
C1 C6 C8 122.9(4) . . ?
C8 O3 Zn1 131.0(3) . . ?
C7 O5 Zn1 131.8(3) . 3_655 ?
O8 C8 O3 121.7(5) . . ?
O8 C8 C6 116.4(4) . . ?
O3 C8 C6 121.9(4) . . ?
O4 C9 O10 123.6(5) . . ?
O4 C9 C4 119.4(5) . . ?
O10 C9 C4 117.0(5) . . ?
C13 N1 C10 117.3(6) . . ?
C13 N1 Zn2 121.3(4) . . ?
C10 N1 Zn2 120.8(5) . . ?
C11 C12 C15 116.1(6) . . ?
C11 C12 C12 121.6(7) . 3_565 ?
C15 C12 C12 122.2(7) . 3_565 ?
N1 C13 C15 124.3(7) . . ?
C12 C11 C10 121.5(7) . . ?
N1 C10 C11 121.6(7) . . ?
C12 C15 C13 118.9(7) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         2.290
_refine_diff_density_min         -1.255
_refine_diff_density_rms         0.111
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.263 0.235 779 174 ' '
_platon_squeeze_details          
;
;
