# Electronic Supplementary Material (ESI) for ChemComm.
# 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_pna21
_database_code_depnum_ccdc_archive 'CCDC 1865413'
loop_
_audit_author_name
_audit_author_address
'Xiao Zhang'
;Harbin Institute of Technology
China
;
_audit_update_record             
;
2018-09-03 deposited with the CCDC.	2020-04-27 downloaded from the CCDC.
;
_audit_creation_date             2018-09-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H20 O8 Zn2'
_chemical_formula_sum            'C16 H20 O8 Zn2'
_chemical_formula_weight         471.06
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   17.8332(5)
_cell_length_b                   9.0061(2)
_cell_length_c                   13.2032(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2120.53(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2403
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8547
_cell_measurement_theta_min      2.7322
_shelx_estimated_absorpt_T_max   0.803
_shelx_estimated_absorpt_T_min   0.657
_exptl_absorpt_coefficient_mu    2.297
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83527
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5890
_diffrn_reflns_point_group_measured_fraction_full 0.776
_diffrn_reflns_point_group_measured_fraction_max 0.776
_diffrn_reflns_theta_full        25.093
_diffrn_reflns_theta_max         25.093
_diffrn_reflns_theta_min         2.738
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9737
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -32.00   79.00   1.0000   14.3400
omega____ theta____ kappa____ phi______ frames
    -       20.8282  -19.0000   90.0000 111

#__ type_ start__ end____ width___ exp.time_
  2 omega   49.00   74.00   1.0000   14.3400
omega____ theta____ kappa____ phi______ frames
    -       20.8282  178.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega  -22.00    8.00   1.0000   14.3400
omega____ theta____ kappa____ phi______ frames
    -      -21.0626  -37.0000  -30.0000 30

#__ type_ start__ end____ width___ exp.time_
  4 omega  -99.00  -74.00   1.0000   14.3400
omega____ theta____ kappa____ phi______ frames
    -      -21.0626 -178.0000   90.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0279479000
_diffrn_orient_matrix_UB_12      -0.0498290000
_diffrn_orient_matrix_UB_13      0.0175326000
_diffrn_orient_matrix_UB_21      -0.0264593000
_diffrn_orient_matrix_UB_22      -0.0586934000
_diffrn_orient_matrix_UB_23      -0.0007364000
_diffrn_orient_matrix_UB_31      0.0100628000
_diffrn_orient_matrix_UB_32      -0.0162688000
_diffrn_orient_matrix_UB_33      -0.0508143000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.484
_reflns_Friedel_fraction_full    0.531
_reflns_Friedel_fraction_max     0.531
_reflns_number_gt                2604
_reflns_number_total             2930
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 759 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         2930
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0299
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0300P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0637
_refine_ls_wR_factor_ref         0.0675
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a X=CH2 refined with riding coordinates:
 C4(H4A,H4B), C8(H8A,H8B), C11(H11A,H11B), C25(H25A,H25B)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C7(H7A,H7B,H7C), C12(H12A,H12B,H12C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.40972(3) 0.92254(6) 0.53699(5) 0.06382(18) Uani 1 1 d . . . . .
Zn2 Zn 0.53339(4) 0.99266(7) 0.71262(6) 0.0692(2) Uani 1 1 d . . . . .
C1 C 0.5666(3) 0.8076(6) 0.5437(5) 0.0686(14) Uani 1 1 d . . . . .
C2 C 0.6179(4) 0.7015(10) 0.4889(5) 0.091(2) Uani 1 1 d . . . . .
C3 C 0.5979(6) 0.6672(13) 0.3890(7) 0.149(4) Uani 1 1 d . . . . .
H3A H 0.605361 0.752846 0.346887 0.223 Uiso 1 1 calc GR . . . .
H3B H 0.546122 0.638291 0.386764 0.223 Uiso 1 1 calc GR . . . .
H3C H 0.628556 0.587033 0.364886 0.223 Uiso 1 1 calc GR . . . .
C4 C 0.6787(4) 0.6438(10) 0.5405(8) 0.132(3) Uani 1 1 d . . . . .
H4A H 0.710290 0.576141 0.508797 0.159 Uiso 1 1 calc R . . . .
H4B H 0.687918 0.672578 0.607001 0.159 Uiso 1 1 calc R . . . .
C5 C 0.3544(3) 0.8613(7) 0.3482(4) 0.0638(14) Uani 1 1 d . . . . .
C6 C 0.3088(4) 0.7786(9) 0.2717(5) 0.0833(19) Uani 1 1 d . . . . .
C7 C 0.2816(6) 0.6331(10) 0.2976(7) 0.145(4) Uani 1 1 d . . . . .
H7A H 0.249664 0.597162 0.244398 0.218 Uiso 1 1 calc GR . . . .
H7B H 0.253617 0.638349 0.359638 0.218 Uiso 1 1 calc GR . . . .
H7C H 0.323227 0.566790 0.306014 0.218 Uiso 1 1 calc GR . . . .
C8 C 0.2928(4) 0.8454(11) 0.1830(5) 0.120(3) Uani 1 1 d . . . . .
H8A H 0.262981 0.797210 0.135424 0.144 Uiso 1 1 calc R . . . .
H8B H 0.311552 0.939596 0.169299 0.144 Uiso 1 1 calc R . . . .
C9 C 0.4511(4) 1.2188(7) 0.5956(5) 0.0734(17) Uani 1 1 d . . . . .
C10 C 0.4397(5) 1.3825(8) 0.5842(7) 0.097(2) Uani 1 1 d . . . . .
C11 C 0.3918(7) 1.4330(10) 0.5102(14) 0.190(7) Uani 1 1 d . . . . .
H11A H 0.385991 1.534464 0.499636 0.229 Uiso 1 1 calc R . . . .
H11B H 0.365119 1.365687 0.470728 0.229 Uiso 1 1 calc R . . . .
C12 C 0.4820(7) 1.4767(8) 0.6469(8) 0.141(4) Uani 1 1 d . . . . .
H12A H 0.464075 1.576755 0.640176 0.212 Uiso 1 1 calc GR . . . .
H12B H 0.533799 1.472404 0.627429 0.212 Uiso 1 1 calc GR . . . .
H12C H 0.476953 1.445377 0.716101 0.212 Uiso 1 1 calc GR . . . .
C24 C 0.3698(7) 0.7806(13) 0.9331(6) 0.163(5) Uani 1 1 d . . . . .
H24A H 0.344657 0.858503 0.969307 0.245 Uiso 1 1 calc GR . . . .
H24B H 0.422712 0.799650 0.932274 0.245 Uiso 1 1 calc GR . . . .
H24C H 0.360370 0.687308 0.965971 0.245 Uiso 1 1 calc GR . . . .
C25 C 0.2765(5) 0.7125(10) 0.8034(7) 0.124(3) Uani 1 1 d . . . . .
H25A H 0.245760 0.669174 0.852039 0.148 Uiso 1 1 calc R . . . .
H25B H 0.262054 0.712751 0.735779 0.148 Uiso 1 1 calc R . . . .
C26 C 0.3421(4) 0.7749(7) 0.8311(5) 0.0783(18) Uani 1 1 d . . . . .
C27 C 0.3911(4) 0.8427(6) 0.7515(4) 0.0650(15) Uani 1 1 d . . . . .
O1 O 0.5886(2) 0.8566(6) 0.6270(3) 0.0917(14) Uani 1 1 d . . . . .
O2 O 0.5051(2) 0.8353(5) 0.5037(3) 0.0838(13) Uani 1 1 d . . . . .
O3 O 0.4005(2) 0.9580(5) 0.3238(3) 0.0768(12) Uani 1 1 d . . . . .
O4 O 0.3439(2) 0.8277(5) 0.4391(3) 0.0755(12) Uani 1 1 d . . . . .
O5 O 0.4074(3) 1.1363(5) 0.5485(4) 0.0850(12) Uani 1 1 d . . . . .
O6 O 0.5015(3) 1.1776(5) 0.6538(4) 0.0848(12) Uani 1 1 d . . . . .
O7 O 0.4510(3) 0.8948(6) 0.7799(3) 0.0938(14) Uani 1 1 d . . . . .
O8 O 0.3679(2) 0.8406(5) 0.6622(3) 0.0809(12) 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 O2 1.925(4) . ?
Zn1 O4 1.943(4) . ?
Zn1 O5 1.932(4) . ?
Zn1 O8 1.958(4) . ?
Zn2 O1 1.936(4) . ?
Zn2 O3 1.935(4) 2_675 ?
Zn2 O6 1.924(5) . ?
Zn2 O7 1.930(5) . ?
C1 C2 1.508(9) . ?
C1 O1 1.248(7) . ?
C1 O2 1.241(7) . ?
C2 C3 1.401(10) . ?
C2 C4 1.382(11) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9300 . ?
C4 H4B 0.9300 . ?
C5 C6 1.496(8) . ?
C5 O3 1.241(7) . ?
C5 O4 1.251(6) . ?
C6 C7 1.439(10) . ?
C6 C8 1.347(9) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9300 . ?
C8 H8B 0.9300 . ?
C9 C10 1.496(9) . ?
C9 O5 1.244(8) . ?
C9 O6 1.239(8) . ?
C10 C11 1.376(15) . ?
C10 C12 1.405(13) . ?
C11 H11A 0.9300 . ?
C11 H11B 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C24 C26 1.435(10) . ?
C25 H25A 0.9300 . ?
C25 H25B 0.9300 . ?
C25 C26 1.348(10) . ?
C26 C27 1.496(9) . ?
C27 O7 1.225(7) . ?
C27 O8 1.251(7) . ?

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 O4 101.67(18) . . ?
O2 Zn1 O5 116.3(2) . . ?
O2 Zn1 O8 112.08(19) . . ?
O4 Zn1 O8 99.54(18) . . ?
O5 Zn1 O4 118.5(2) . . ?
O5 Zn1 O8 107.5(2) . . ?
O3 Zn2 O1 106.19(19) 2_675 . ?
O6 Zn2 O1 117.5(2) . . ?
O6 Zn2 O3 106.7(2) . 2_675 ?
O6 Zn2 O7 110.9(2) . . ?
O7 Zn2 O1 111.5(2) . . ?
O7 Zn2 O3 102.69(19) . 2_675 ?
O1 C1 C2 117.1(6) . . ?
O2 C1 C2 117.3(6) . . ?
O2 C1 O1 125.5(5) . . ?
C3 C2 C1 115.9(7) . . ?
C4 C2 C1 118.5(7) . . ?
C4 C2 C3 125.5(8) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 120.0 . . ?
C2 C4 H4B 120.0 . . ?
H4A C4 H4B 120.0 . . ?
O3 C5 C6 122.3(5) . . ?
O3 C5 O4 121.1(6) . . ?
O4 C5 C6 116.5(6) . . ?
C7 C6 C5 118.4(6) . . ?
C8 C6 C5 118.7(7) . . ?
C8 C6 C7 122.8(7) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 120.0 . . ?
C6 C8 H8B 120.0 . . ?
H8A C8 H8B 120.0 . . ?
O5 C9 C10 116.9(7) . . ?
O6 C9 C10 117.1(7) . . ?
O6 C9 O5 125.9(6) . . ?
C11 C10 C9 118.8(9) . . ?
C11 C10 C12 123.5(8) . . ?
C12 C10 C9 117.6(8) . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C24 H24A 109.5 . . ?
C26 C24 H24B 109.5 . . ?
C26 C24 H24C 109.5 . . ?
H25A C25 H25B 120.0 . . ?
C26 C25 H25A 120.0 . . ?
C26 C25 H25B 120.0 . . ?
C24 C26 C27 116.4(7) . . ?
C25 C26 C24 124.5(7) . . ?
C25 C26 C27 119.1(6) . . ?
O7 C27 C26 116.8(6) . . ?
O7 C27 O8 125.7(6) . . ?
O8 C27 C26 117.5(6) . . ?
C1 O1 Zn2 125.4(4) . . ?
C1 O2 Zn1 139.9(4) . . ?
C5 O3 Zn2 139.6(4) . 2_674 ?
C5 O4 Zn1 116.2(4) . . ?
C9 O5 Zn1 128.4(4) . . ?
C9 O6 Zn2 136.3(4) . . ?
C27 O7 Zn2 134.3(4) . . ?
C27 O8 Zn1 131.6(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
