# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_55
_database_code_depnum_ccdc_archive 'CCDC 1527717'
_audit_update_record             
;
2018-05-18 deposited with the CCDC.	2020-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H3 O5 Zn'
_chemical_formula_sum            'C11 H3 O5 Zn'
_chemical_formula_weight         280.52

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           Trigonal
_symmetry_space_group_name_H-M   R-3m
_symmetry_space_group_name_hall  '-R 3 2'

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

_cell_length_a                   18.940(3)
_cell_length_b                   18.940(3)
_cell_length_c                   38.348(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     11913(5)
_cell_formula_units_Z            18
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    48381
_cell_measurement_theta_min      5.069
_cell_measurement_theta_max      47.002

_exptl_crystal_description       diamond
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.704
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2502
_exptl_absorpt_coefficient_mu    0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.757
_exptl_absorpt_correction_T_max  0.830
_exptl_absorpt_process_details   adabs(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         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            48223
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         2.70
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2573
_reflns_number_gt                2058
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_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 > 2σ(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)+(0.1860P)²+60.5526P] 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         2573
_refine_ls_number_parameters     95
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0746
_refine_ls_wR_factor_ref         0.2870
_refine_ls_wR_factor_gt          0.2653
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_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
C6A C 0.2416(9) -0.1467(12) -0.1554(4) 0.089(8) Uani 0.54(3) 1 d P A 1
C6B C 0.2281(9) -0.1332(13) -0.1895(5) 0.085(9) Uani 0.46(3) 1 d P . 2
Zn1 Zn -0.05130(5) -0.52565(2) -0.032082(19) 0.0406(4) Uani 1 2 d S . .
O1 O 0.0346(3) -0.4083(3) -0.04368(12) 0.0716(13) Uani 1 1 d . . .
O2 O 0.1120(3) -0.3705(3) 0.00401(13) 0.0721(14) Uani 1 1 d . . .
O5 O -0.1112(6) -0.5556(3) -0.0763(2) 0.115(3) Uani 1 2 d S . .
C1 C 0.0949(4) -0.3592(4) -0.02662(17) 0.0580(15) Uani 1 1 d . . .
C2 C 0.1538(4) -0.2805(4) -0.04348(17) 0.0607(16) Uani 1 1 d . . .
C3 C 0.1395(4) -0.2658(4) -0.07820(17) 0.0657(18) Uani 1 1 d . . .
H3 H 0.0926 -0.3041 -0.0897 0.079 Uiso 1 1 calc R . .
C4 C 0.1949(3) -0.1949(3) -0.0953(3) 0.068(3) Uani 1 2 d S A .
C5 C 0.1801(4) -0.1801(4) -0.1324(3) 0.071(3) Uani 1 2 d S . .
C7 C 0.2242(3) -0.2242(3) -0.0267(2) 0.057(2) Uani 1 2 d S . .
H7 H 0.2338 -0.2338 -0.0039 0.069 Uiso 1 2 calc SR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C6A 0.060(9) 0.102(13) 0.067(9) 0.024(8) -0.007(7) 0.013(9)
C6B 0.049(9) 0.099(16) 0.063(10) 0.024(10) -0.011(7) 0.005(9)
Zn1 0.0326(5) 0.0532(6) 0.0290(6) -0.00180(15) -0.0036(3) 0.0163(3)
O1 0.058(3) 0.059(3) 0.067(3) 0.013(2) 0.002(2) 0.007(2)
O2 0.068(3) 0.066(3) 0.063(3) 0.017(2) 0.003(2) 0.019(2)
O5 0.141(8) 0.134(6) 0.072(5) -0.035(3) -0.069(5) 0.071(4)
C1 0.047(3) 0.054(4) 0.059(4) 0.008(3) 0.010(3) 0.014(3)
C2 0.056(4) 0.061(4) 0.054(3) 0.007(3) 0.003(3) 0.020(3)
C3 0.056(4) 0.059(4) 0.056(4) 0.003(3) -0.011(3) 0.010(3)
C4 0.058(4) 0.058(4) 0.058(6) 0.011(3) -0.011(3) 0.006(4)
C5 0.057(3) 0.057(3) 0.060(6) 0.008(3) -0.008(3) 0.000(5)
C7 0.056(3) 0.056(3) 0.044(4) 0.004(2) -0.004(2) 0.016(4)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C6A C5 1.341(18) . ?
C6A C6A 1.80(3) 22 ?
C6A C6A 2.00(4) 16_544 ?
C6B C5 1.345(18) 31_544 ?
C6B C6B 1.80(3) 22 ?
C6B C6B 1.98(5) 16_544 ?
Zn1 O5 1.960(7) . ?
Zn1 O2 2.022(5) 5 ?
Zn1 O2 2.022(5) 19_545 ?
Zn1 O1 2.043(4) . ?
Zn1 O1 2.043(4) 23_545 ?
Zn1 Zn1 2.9811(15) 19_545 ?
O1 C1 1.238(8) . ?
O2 C1 1.265(8) . ?
O2 Zn1 2.022(5) 19_545 ?
C1 C2 1.490(9) . ?
C2 C7 1.381(8) . ?
C2 C3 1.413(9) . ?
C3 C4 1.388(8) . ?
C3 H3 0.9300 . ?
C4 C3 1.388(8) 22 ?
C4 C5 1.503(14) . ?
C5 C6A 1.341(18) 22 ?
C5 C6B 1.345(18) 31_544 ?
C5 C6B 1.345(18) 16_544 ?
C7 C2 1.381(8) 22 ?
C7 H7 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
C5 C6A C6A 47.9(9) . 22 ?
C5 C6A C6A 88.6(16) . 16_544 ?
C6A C6A C6A 90.000(3) 22 16_544 ?
C5 C6B C6B 48.1(10) 31_544 22 ?
C5 C6B C6B 88.8(17) 31_544 16_544 ?
C6B C6B C6B 90.000(2) 22 16_544 ?
O5 Zn1 O2 102.3(3) . 5 ?
O5 Zn1 O2 102.3(3) . 19_545 ?
O2 Zn1 O2 87.0(3) 5 19_545 ?
O5 Zn1 O1 99.0(3) . . ?
O2 Zn1 O1 88.9(2) 5 . ?
O2 Zn1 O1 158.6(2) 19_545 . ?
O5 Zn1 O1 99.0(3) . 23_545 ?
O2 Zn1 O1 158.6(2) 5 23_545 ?
O2 Zn1 O1 88.9(2) 19_545 23_545 ?
O1 Zn1 O1 87.3(3) . 23_545 ?
O5 Zn1 Zn1 175.7(3) . 19_545 ?
O2 Zn1 Zn1 80.72(14) 5 19_545 ?
O2 Zn1 Zn1 80.72(14) 19_545 19_545 ?
O1 Zn1 Zn1 77.88(14) . 19_545 ?
O1 Zn1 Zn1 77.88(14) 23_545 19_545 ?
C1 O1 Zn1 129.4(4) . . ?
C1 O2 Zn1 126.1(4) . 19_545 ?
O1 C1 O2 125.6(6) . . ?
O1 C1 C2 118.0(6) . . ?
O2 C1 C2 116.4(6) . . ?
C7 C2 C3 119.4(6) . . ?
C7 C2 C1 121.4(6) . . ?
C3 C2 C1 119.0(6) . . ?
C4 C3 C2 120.6(6) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C3 119.1(9) . 22 ?
C3 C4 C5 120.4(4) . . ?
C3 C4 C5 120.4(4) 22 . ?
C6A C5 C6A 84.2(17) . 22 ?
C6A C5 C6B 117.6(12) . 31_544 ?
C6A C5 C6B 64.3(12) 22 31_544 ?
C6A C5 C6B 64.3(12) . 16_544 ?
C6A C5 C6B 117.6(12) 22 16_544 ?
C6B C5 C6B 83.9(19) 31_544 16_544 ?
C6A C5 C4 120.8(10) . . ?
C6A C5 C4 120.8(10) 22 . ?
C6B C5 C4 121.6(10) 31_544 . ?
C6B C5 C4 121.6(10) 16_544 . ?
C2 C7 C2 120.8(8) . 22 ?
C2 C7 H7 119.6 . . ?
C2 C7 H7 119.6 22 . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.850
_refine_diff_density_min         -0.830
_refine_diff_density_rms         0.287

# 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 -0.048 -0.029 -0.002 8050 2824 ' '
_platon_squeeze_details          
;
;
