# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_Zn
_database_code_depnum_ccdc_archive 'CCDC 1545845'
_audit_update_record             
;
2017-04-25 deposited with the CCDC.
2017-06-05 downloaded from the CCDC.
;

_vrf_PLAT602_Zn                  
;
PROBLEM:    VERY LARGE Solvent Accessible VOID(S) in Structure        ! Info 

RESPONSE:   cation and solvent molecules per unit cell squeezed.
;

_vrf_PLAT029_Zn                  
;
PROBLEM:  _diffrn_measured_fraction_theta_full value Low .      0.834 Note 
RESPONSE: The fraction is complete when the twin fractions were separated by
using the detwinning tool in PLATON, but is only 0.90 when the raw intensities
were physically separately into two overlapping hkl sets with the APEX2 
detwinning program.
;


_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H9 O11 Zn2'
_chemical_formula_weight         592.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 '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, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.0940(6)
_cell_length_b                   12.7134(5)
_cell_length_c                   33.9463(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3924.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4812
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      25.31

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.002
_exptl_crystal_F_000             1180
_exptl_transmission_factor_min   0
_exptl_transmission_factor_max   0
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    1.834
_shelx_estimated_absorpt_T_min   0.688
_shelx_estimated_absorpt_T_max   0.882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5712
_diffrn_reflns_av_unetI/netI     0.0865
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         5.519
_diffrn_reflns_theta_max         73.285
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.804
_diffrn_measured_fraction_theta_full 0.834
_diffrn_reflns_Laue_measured_fraction_max 0.804
_diffrn_reflns_Laue_measured_fraction_full 0.834
_diffrn_reflns_point_group_measured_fraction_max 0.600
_diffrn_reflns_point_group_measured_fraction_full 0.629
_reflns_number_total             4743
_reflns_number_gt                4038
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.325
_reflns_Friedel_fraction_max     0.338
_reflns_Friedel_fraction_full    0.360

_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       APEX
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.1906P)²+1.2000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0027(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.24(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4743
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0878
_refine_ls_wR_factor_ref         0.2531
_refine_ls_wR_factor_gt          0.2365
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_restrained_S_all      0.987
_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_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 -0.09824(19) 0.81472(9) 0.17965(3) 0.0393(5) Uani 1 1 d . . . . .
Zn2 Zn 1.23690(17) 0.23644(9) 0.40901(3) 0.0369(4) Uani 1 1 d . . . . .
O4 O 0.2793(11) 1.1223(5) 0.3726(2) 0.0472(19) Uani 1 1 d . . . . .
O6 O 0.3491(12) 0.3648(6) 0.3993(3) 0.054(2) Uani 1 1 d . . . . .
O9 O 0.7736(11) 0.3055(6) 0.5374(2) 0.0495(19) Uani 1 1 d . . . . .
O7 O 0.9323(14) 0.3425(9) 0.3579(2) 0.068(3) Uani 1 1 d . . . . .
C9 C 0.3632(12) 0.7258(7) 0.3594(3) 0.038(2) Uani 1 1 d . . . . .
O10 O 0.6010(16) 0.4280(9) 0.5458(3) 0.073(3) Uani 1 1 d . . . . .
C2 C 0.1473(15) 0.8619(9) 0.2792(3) 0.044(2) Uani 1 1 d . . . . .
O3 O 0.1174(19) 1.1627(7) 0.3265(4) 0.087(5) Uani 1 1 d . . . . .
O2 O 0.102(2) 0.7468(8) 0.2257(3) 0.083(4) Uani 1 1 d . . . . .
O8 O 1.0386(12) 0.2857(10) 0.4134(3) 0.068(3) Uani 1 1 d . . . . .
O5 O 0.2394(19) 0.4164(6) 0.3443(3) 0.082(4) Uani 1 1 d . . . . .
C3 C 0.1425(16) 0.9663(8) 0.2928(3) 0.046(3) Uani 1 1 d . . . . .
H3 H 0.095765 1.019929 0.277927 0.056 Uiso 1 1 calc R U . . .
C20 C 0.8027(15) 0.3515(8) 0.4587(3) 0.046(3) Uani 1 1 d . . . . .
H20 H 0.871981 0.306404 0.471057 0.055 Uiso 1 1 calc R U . . .
C10 C 0.3164(16) 0.6208(8) 0.3562(3) 0.044(3) Uani 1 1 d . . . . .
H10 H 0.236906 0.604182 0.339098 0.053 Uiso 1 1 calc R U . . .
C7 C 0.2868(13) 0.8097(7) 0.3362(3) 0.039(2) Uani 1 1 d . . . . .
C18 C 0.8118(14) 0.3716(9) 0.4183(3) 0.042(2) Uani 1 1 d . . . . .
C8 C 0.2196(15) 0.7869(7) 0.3002(3) 0.045(3) Uani 1 1 d . . . . .
H8 H 0.224423 0.717292 0.290183 0.054 Uiso 1 1 calc R U . . .
O1 O -0.0156(17) 0.8913(10) 0.2257(3) 0.080(4) Uani 1 1 d . . . . .
C11 C 0.3847(15) 0.5402(7) 0.3775(3) 0.041(2) Uani 1 1 d . . . . .
C6 C 0.2822(15) 0.9136(8) 0.3497(3) 0.040(2) Uani 1 1 d . . . . .
H6 H 0.330265 0.932873 0.373461 0.048 Uiso 1 1 calc R U . . .
C17 C 0.7080(13) 0.4379(9) 0.4006(3) 0.042(2) Uani 1 1 d . . . . .
H17 H 0.712579 0.449901 0.373026 0.050 Uiso 1 1 calc R U . . .
C4 C 0.2069(14) 0.9879(8) 0.3280(3) 0.043(2) Uani 1 1 d . . . . .
C5 C 0.2007(15) 1.1004(8) 0.3431(3) 0.044(3) Uani 1 1 d . . . . .
C22 C 0.5939(15) 0.4676(9) 0.4630(3) 0.046(2) Uani 1 1 d . . . . .
H22 H 0.523191 0.502792 0.478815 0.056 Uiso 1 1 calc R U . . .
C21 C 0.6912(15) 0.3981(9) 0.4806(3) 0.046(3) Uani 1 1 d . . . . .
C12 C 0.3206(16) 0.4326(8) 0.3736(3) 0.043(2) Uani 1 1 d . . . . .
C19 C 0.9368(16) 0.3279(10) 0.3947(3) 0.051(3) Uani 1 1 d . . . . .
C16 C 0.5975(15) 0.4868(8) 0.4228(3) 0.042(2) Uani 1 1 d . . . . .
C13 C 0.4997(13) 0.5647(8) 0.4026(3) 0.042(2) Uani 1 1 d . . . . .
C15 C 0.4737(16) 0.7473(8) 0.3856(4) 0.053(3) Uani 1 1 d . . . . .
H15 H 0.502154 0.818372 0.389757 0.064 Uiso 1 1 calc R U . . .
C23 C 0.6860(16) 0.3778(10) 0.5243(4) 0.050(3) Uani 1 1 d . . . . .
C1 C 0.0751(18) 0.8308(10) 0.2408(3) 0.052(3) Uani 1 1 d . . . . .
C14 C 0.5447(17) 0.6688(9) 0.4062(4) 0.055(3) Uani 1 1 d . . . . .
H14 H 0.625005 0.685915 0.422925 0.066 Uiso 1 1 calc R U . . .
O11 O -0.281(2) 0.779(2) 0.2175(6) 0.136(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O3 1.952(9) 4_545 ?
Zn1 O1 1.990(11) . ?
Zn1 O5 1.995(10) 4 ?
Zn1 O7 2.007(11) 4_655 ?
Zn1 O11 2.148(17) . ?
Zn2 O8 1.915(10) . ?
Zn2 O9 1.926(7) 3_556 ?
Zn2 O4 1.945(7) 1_645 ?
Zn2 O6 1.953(9) 1_655 ?
O4 C5 1.262(15) . ?
O6 C12 1.254(14) . ?
O9 C23 1.295(16) . ?
O7 C19 1.262(15) . ?
C9 C15 1.370(18) . ?
C9 C10 1.405(14) . ?
C9 C7 1.497(14) . ?
O10 C23 1.241(17) . ?
C2 C8 1.360(16) . ?
C2 C3 1.406(14) . ?
C2 C1 1.510(15) . ?
O3 C5 1.232(16) . ?
O2 C1 1.211(17) . ?
O8 C19 1.244(18) . ?
O5 C12 1.256(16) . ?
C3 C4 1.357(16) . ?
C3 H3 0.9500 . ?
C20 C21 1.390(18) . ?
C20 C18 1.396(15) . ?
C20 H20 0.9500 . ?
C10 C11 1.401(15) . ?
C10 H10 0.9500 . ?
C7 C8 1.397(15) . ?
C7 C6 1.398(13) . ?
C18 C17 1.401(16) . ?
C18 C19 1.499(18) . ?
C8 H8 0.9500 . ?
O1 C1 1.239(19) . ?
C11 C13 1.383(18) . ?
C11 C12 1.494(14) . ?
C6 C4 1.380(15) . ?
C6 H6 0.9500 . ?
C17 C16 1.401(18) . ?
C17 H17 0.9500 . ?
C4 C5 1.520(13) . ?
C22 C16 1.387(16) . ?
C22 C21 1.385(18) . ?
C22 H22 0.9500 . ?
C21 C23 1.506(16) . ?
C16 C13 1.498(16) . ?
C13 C14 1.390(15) . ?
C15 C14 1.379(17) . ?
C15 H15 0.9500 . ?
C14 H14 0.9500 . ?

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 127.0(5) 4_545 . ?
O3 Zn1 O5 122.8(5) 4_545 4 ?
O1 Zn1 O5 104.2(4) . 4 ?
O3 Zn1 O7 100.0(6) 4_545 4_655 ?
O1 Zn1 O7 97.4(5) . 4_655 ?
O5 Zn1 O7 96.4(6) 4 4_655 ?
O3 Zn1 O11 77.6(9) 4_545 . ?
O1 Zn1 O11 85.8(8) . . ?
O5 Zn1 O11 83.3(8) 4 . ?
O7 Zn1 O11 176.7(7) 4_655 . ?
O8 Zn2 O9 100.4(4) . 3_556 ?
O8 Zn2 O4 118.7(5) . 1_645 ?
O9 Zn2 O4 111.1(3) 3_556 1_645 ?
O8 Zn2 O6 103.4(5) . 1_655 ?
O9 Zn2 O6 107.5(4) 3_556 1_655 ?
O4 Zn2 O6 114.4(4) 1_645 1_655 ?
C5 O4 Zn2 123.9(8) . 1_465 ?
C12 O6 Zn2 125.7(9) . 1_455 ?
C23 O9 Zn2 114.5(7) . 3_456 ?
C19 O7 Zn1 125.3(9) . 4_645 ?
C15 C9 C10 117.6(10) . . ?
C15 C9 C7 122.6(9) . . ?
C10 C9 C7 119.7(10) . . ?
C8 C2 C3 120.2(10) . . ?
C8 C2 C1 118.6(10) . . ?
C3 C2 C1 121.2(11) . . ?
C5 O3 Zn1 137.7(10) . 4 ?
C19 O8 Zn2 143.4(8) . . ?
C12 O5 Zn1 143.8(8) . 4_545 ?
C4 C3 C2 117.9(10) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C21 C20 C18 119.4(11) . . ?
C21 C20 H20 120.3 . . ?
C18 C20 H20 120.3 . . ?
C11 C10 C9 121.3(11) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C8 C7 C6 117.9(9) . . ?
C8 C7 C9 121.0(9) . . ?
C6 C7 C9 121.1(9) . . ?
C20 C18 C17 119.4(10) . . ?
C20 C18 C19 120.2(10) . . ?
C17 C18 C19 120.3(9) . . ?
C2 C8 C7 121.7(9) . . ?
C2 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C1 O1 Zn1 105.9(8) . . ?
C10 C11 C13 119.3(10) . . ?
C10 C11 C12 116.8(11) . . ?
C13 C11 C12 123.8(10) . . ?
C4 C6 C7 119.2(9) . . ?
C4 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C16 C17 C18 121.3(9) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.3 . . ?
C3 C4 C6 123.0(9) . . ?
C3 C4 C5 118.1(9) . . ?
C6 C4 C5 118.8(9) . . ?
O3 C5 O4 124.7(10) . . ?
O3 C5 C4 118.3(10) . . ?
O4 C5 C4 117.0(9) . . ?
C16 C22 C21 121.4(11) . . ?
C16 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C20 C21 C22 120.4(10) . . ?
C20 C21 C23 118.4(11) . . ?
C22 C21 C23 120.9(10) . . ?
O6 C12 O5 124.2(10) . . ?
O6 C12 C11 119.1(10) . . ?
O5 C12 C11 116.8(9) . . ?
O8 C19 O7 126.3(12) . . ?
O8 C19 C18 116.8(10) . . ?
O7 C19 C18 116.8(11) . . ?
C22 C16 C17 117.9(10) . . ?
C22 C16 C13 123.6(10) . . ?
C17 C16 C13 118.3(10) . . ?
C14 C13 C11 119.4(10) . . ?
C14 C13 C16 114.5(11) . . ?
C11 C13 C16 125.5(10) . . ?
C9 C15 C14 121.9(10) . . ?
C9 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
O10 C23 O9 123.1(11) . . ?
O10 C23 C21 120.7(11) . . ?
O9 C23 C21 116.1(10) . . ?
O2 C1 O1 120.6(11) . . ?
O2 C1 C2 120.5(13) . . ?
O1 C1 C2 119.0(11) . . ?
C15 C14 C13 120.4(12) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?

_refine_diff_density_max         1.236
_refine_diff_density_min         -0.633
_refine_diff_density_rms         0.160

