# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_ZnBLD-dPLA
_database_code_depnum_ccdc_archive 'CCDC 1908241'
loop_
_audit_author_name
_audit_author_address
'Andrew White'
;Imperial College London
United Kingdom
;
_audit_update_record             
;
2019-04-05 deposited with the CCDC.	2019-05-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 N O8 Zn2, 1.5(C3 H7 N O)'
_chemical_formula_sum            'C18.50 H25.50 N2.50 O9.50 Zn2'
_chemical_formula_weight         565.65

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'
N N 0.0311 0.0180 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.3034(4)
_cell_length_b                   11.7652(9)
_cell_length_c                   20.3570(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2467.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2641
_cell_measurement_theta_min      4.2670
_cell_measurement_theta_max      73.2610

_exptl_crystal_description       'blocky needles'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_F_000             1160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.348
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.117
_exptl_absorpt_coefficient_mu    2.850
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.534
_exptl_absorpt_correction_T_max  0.763
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_measurement_device_type  'Agilent Xcalibur PX Ultra A'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 10.4115
_diffrn_reflns_number            7563
_diffrn_reflns_av_unetI/netI     0.0527
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.340
_diffrn_reflns_theta_max         73.277
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             4699
_reflns_number_gt                4140
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_max     0.921
_reflns_Friedel_fraction_full    0.968

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 Structure factors included contributions from the .fab file. 
  
 _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       'CrysAlisPro, Rigaku OD'
_computing_cell_refinement       'CrysAlisPro, Rigaku OD'
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2017)'
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0628P)²+1.3461P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1517 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.08(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4699
_refine_ls_number_parameters     245
_refine_ls_number_restraints     143
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1209
_refine_ls_wR_factor_gt          0.1155
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.046
_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 0.15034(7) 0.32413(7) 0.50865(4) 0.0245(2) Uani 1 1 d . . . . .
Zn2 Zn 0.46297(7) 0.42053(7) 0.50973(4) 0.0241(2) Uani 1 1 d . . . . .
C1 C 0.2831(7) 0.4312(8) 0.6235(3) 0.0333(16) Uani 1 1 d D . . . .
O2 O 0.1865(5) 0.3885(6) 0.5968(2) 0.0445(15) Uani 1 1 d . . . . .
O3 O 0.3915(5) 0.4537(5) 0.5977(2) 0.0396(13) Uani 1 1 d . . . . .
C4 C 0.2696(9) 0.4565(10) 0.6963(3) 0.037(6) Uani 0.59(2) 1 d DG U P A 1
C5 C 0.1556(9) 0.4284(14) 0.7289(4) 0.039(4) Uani 0.59(2) 1 d G U P A 1
H5A H 0.088275 0.389526 0.706318 0.047 Uiso 0.59(2) 1 calc R U P A 1
C6 C 0.1401(9) 0.4572(14) 0.7947(4) 0.042(4) Uani 0.59(2) 1 d G U P A 1
H6A H 0.062125 0.437920 0.817022 0.051 Uiso 0.59(2) 1 calc R U P A 1
C7 C 0.2386(9) 0.5140(9) 0.8278(3) 0.030(5) Uani 0.59(2) 1 d DG U P A 1
C8 C 0.3526(10) 0.5422(12) 0.7951(4) 0.035(3) Uani 0.59(2) 1 d G U P A 1
H8A H 0.419924 0.581057 0.817774 0.041 Uiso 0.59(2) 1 calc R U P A 1
C9 C 0.3681(10) 0.5134(13) 0.7294(4) 0.035(3) Uani 0.59(2) 1 d G U P A 1
H9A H 0.446076 0.532663 0.707069 0.042 Uiso 0.59(2) 1 calc R U P A 1
C4' C 0.2701(14) 0.4663(13) 0.6945(4) 0.037(8) Uiso 0.41(2) 1 d DG U P A 2
C5' C 0.1475(12) 0.4883(17) 0.7199(5) 0.029(4) Uiso 0.41(2) 1 d G U P A 2
H5B H 0.073307 0.483323 0.692340 0.035 Uiso 0.41(2) 1 calc R U P A 2
C6' C 0.1333(12) 0.5174(17) 0.7857(5) 0.032(4) Uiso 0.41(2) 1 d G U P A 2
H6B H 0.049423 0.532434 0.803070 0.039 Uiso 0.41(2) 1 calc R U P A 2
C7' C 0.2418(14) 0.5246(13) 0.8261(4) 0.031(8) Uiso 0.41(2) 1 d DG U P A 2
C8' C 0.3644(12) 0.5027(14) 0.8007(6) 0.025(4) Uiso 0.41(2) 1 d G U P A 2
H8B H 0.438598 0.507608 0.828253 0.031 Uiso 0.41(2) 1 calc R U P A 2
C9' C 0.3786(12) 0.4735(14) 0.7349(6) 0.032(5) Uiso 0.41(2) 1 d G U P A 2
H9B H 0.462485 0.458497 0.717523 0.038 Uiso 0.41(2) 1 calc R U P A 2
C10 C 0.2232(7) 0.5488(7) 0.8988(3) 0.0322(16) Uani 1 1 d D . . . .
O11 O 0.1133(5) 0.5401(5) 0.9226(2) 0.0419(14) Uani 1 1 d . . . . .
O12 O 0.3245(5) 0.5810(5) 0.9288(2) 0.0362(11) Uani 1 1 d . . . . .
C21 C 0.3635(5) 0.1695(6) 0.4866(3) 0.0292(12) Uani 1 1 d . . . . .
O22 O 0.3484(4) 0.2701(4) 0.5056(2) 0.0284(9) Uani 1 1 d . . . . .
O23 O 0.4677(4) 0.1196(4) 0.4798(3) 0.0424(13) Uani 1 1 d . . . . .
C24 C 0.2381(6) 0.1037(7) 0.4675(4) 0.0346(17) Uani 1 1 d . . . . .
H24A H 0.241272 0.026583 0.488092 0.042 Uiso 1 1 calc R U . . .
O25 O 0.1270(4) 0.1610(4) 0.4908(2) 0.0297(9) Uani 1 1 d . . . . .
C26 C 0.2363(8) 0.0899(11) 0.3927(4) 0.063(3) Uani 1 1 d . . . . .
H26A H 0.146472 0.082262 0.377607 0.095 Uiso 1 1 calc R U . . .
H26B H 0.285498 0.021815 0.380493 0.095 Uiso 1 1 calc R U . . .
H26C H 0.275943 0.156823 0.372221 0.095 Uiso 1 1 calc R U . . .
O30 O 0.5430(5) 0.5841(5) 0.5122(3) 0.0470(12) Uani 1 1 d D . . . .
C30 C 0.539(2) 0.6558(13) 0.4687(11) 0.059(5) Uani 0.550(18) 1 d D U P B 1
H30A H 0.477945 0.642158 0.434653 0.071 Uiso 0.550(18) 1 calc R U P B 1
N31 N 0.6106(18) 0.7520(13) 0.4625(10) 0.076(4) Uani 0.550(18) 1 d D U P B 1
C32 C 0.707(2) 0.779(2) 0.5104(13) 0.094(6) Uani 0.550(18) 1 d D U P B 1
H32A H 0.749548 0.850654 0.498662 0.142 Uiso 0.550(18) 1 calc R U P B 1
H32B H 0.666395 0.786310 0.553670 0.142 Uiso 0.550(18) 1 calc R U P B 1
H32C H 0.772201 0.718015 0.511785 0.142 Uiso 0.550(18) 1 calc R U P B 1
C33 C 0.599(3) 0.833(2) 0.4097(14) 0.106(7) Uani 0.550(18) 1 d D U P B 1
H33A H 0.661603 0.895085 0.416548 0.159 Uiso 0.550(18) 1 calc R U P B 1
H33B H 0.617820 0.795504 0.367796 0.159 Uiso 0.550(18) 1 calc R U P B 1
H33C H 0.511107 0.864163 0.408885 0.159 Uiso 0.550(18) 1 calc R U P B 1
C30' C 0.546(2) 0.6596(19) 0.4726(13) 0.065(7) Uiso 0.450(18) 1 d D U P B 2
H30B H 0.525301 0.646822 0.427763 0.078 Uiso 0.450(18) 1 calc R U P B 2
N31' N 0.581(2) 0.7633(17) 0.4945(12) 0.076(5) Uiso 0.450(18) 1 d D U P B 2
C32' C 0.622(4) 0.788(3) 0.5612(14) 0.117(10) Uiso 0.450(18) 1 d D U P B 2
H32D H 0.641958 0.869352 0.565087 0.176 Uiso 0.450(18) 1 calc R U P B 2
H32E H 0.551535 0.768814 0.591719 0.176 Uiso 0.450(18) 1 calc R U P B 2
H32F H 0.699014 0.743392 0.571908 0.176 Uiso 0.450(18) 1 calc R U P B 2
C33' C 0.597(3) 0.861(2) 0.4519(16) 0.095(7) Uiso 0.450(18) 1 d D U P B 2
H33D H 0.622566 0.927512 0.478291 0.142 Uiso 0.450(18) 1 calc R U P B 2
H33E H 0.664525 0.845584 0.419240 0.142 Uiso 0.450(18) 1 calc R U P B 2
H33F H 0.514932 0.877583 0.429509 0.142 Uiso 0.450(18) 1 calc R U P B 2


_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 O25 1.968(5) . ?
Zn1 O2 1.982(5) . ?
Zn1 O12 1.989(5) 2_564 ?
Zn1 O23 2.008(5) 4_456 ?
Zn1 O22 2.138(4) . ?
Zn2 O25 1.944(4) 4_556 ?
Zn2 O3 1.976(5) . ?
Zn2 O11 1.996(5) 2_564 ?
Zn2 O30 2.095(5) . ?
Zn2 O22 2.129(4) . ?
C1 O2 1.240(9) . ?
C1 O3 1.262(9) . ?
C1 C4' 1.510(10) . ?
C1 C4 1.519(8) . ?
C4 C5 1.3900 . ?
C4 C9 1.3900 . ?
C5 C6 1.3900 . ?
C6 C7 1.3900 . ?
C7 C8 1.3900 . ?
C7 C10 1.511(8) . ?
C8 C9 1.3900 . ?
C4' C5' 1.3900 . ?
C4' C9' 1.3900 . ?
C5' C6' 1.3900 . ?
C6' C7' 1.3900 . ?
C7' C8' 1.3900 . ?
C7' C10 1.521(10) . ?
C8' C9' 1.3900 . ?
C10 O11 1.235(9) . ?
C10 O12 1.267(9) . ?
C21 O23 1.231(8) . ?
C21 O22 1.255(8) . ?
C21 C24 1.556(8) . ?
C24 O25 1.410(8) . ?
C24 C26 1.532(11) . ?
O30 C30' 1.20(2) . ?
O30 C30 1.224(19) . ?
C30 N31 1.357(18) . ?
N31 C32 1.43(2) . ?
N31 C33 1.44(2) . ?
C30' N31' 1.35(2) . ?
N31' C32' 1.45(2) . ?
N31' C33' 1.45(2) . ?

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
O25 Zn1 O2 124.3(2) . . ?
O25 Zn1 O12 114.3(2) . 2_564 ?
O2 Zn1 O12 120.0(3) . 2_564 ?
O25 Zn1 O23 103.23(18) . 4_456 ?
O2 Zn1 O23 86.8(2) . 4_456 ?
O12 Zn1 O23 91.9(2) 2_564 4_456 ?
O25 Zn1 O22 79.70(16) . . ?
O2 Zn1 O22 87.73(19) . . ?
O12 Zn1 O22 91.06(19) 2_564 . ?
O23 Zn1 O22 174.5(2) 4_456 . ?
O25 Zn2 O3 115.2(2) 4_556 . ?
O25 Zn2 O11 116.9(2) 4_556 2_564 ?
O3 Zn2 O11 127.8(2) . 2_564 ?
O25 Zn2 O30 96.4(2) 4_556 . ?
O3 Zn2 O30 86.7(2) . . ?
O11 Zn2 O30 87.9(2) 2_564 . ?
O25 Zn2 O22 94.11(17) 4_556 . ?
O3 Zn2 O22 89.6(2) . . ?
O11 Zn2 O22 86.5(2) 2_564 . ?
O30 Zn2 O22 169.46(18) . . ?
O2 C1 O3 127.8(6) . . ?
O2 C1 C4' 117.4(8) . . ?
O3 C1 C4' 114.7(8) . . ?
O2 C1 C4 115.7(6) . . ?
O3 C1 C4 116.4(7) . . ?
C1 O2 Zn1 134.6(4) . . ?
C1 O3 Zn2 131.7(5) . . ?
C5 C4 C9 120.0 . . ?
C5 C4 C1 119.8(6) . . ?
C9 C4 C1 120.1(6) . . ?
C4 C5 C6 120.0 . . ?
C7 C6 C5 120.0 . . ?
C8 C7 C6 120.0 . . ?
C8 C7 C10 118.8(6) . . ?
C6 C7 C10 121.2(6) . . ?
C7 C8 C9 120.0 . . ?
C8 C9 C4 120.0 . . ?
C5' C4' C9' 120.0 . . ?
C5' C4' C1 119.2(9) . . ?
C9' C4' C1 120.8(9) . . ?
C6' C5' C4' 120.0 . . ?
C5' C6' C7' 120.0 . . ?
C8' C7' C6' 120.0 . . ?
C8' C7' C10 120.8(9) . . ?
C6' C7' C10 119.1(9) . . ?
C7' C8' C9' 120.0 . . ?
C8' C9' C4' 120.0 . . ?
O11 C10 O12 126.3(6) . . ?
O11 C10 C7 116.6(7) . . ?
O12 C10 C7 117.1(7) . . ?
O11 C10 C7' 118.7(8) . . ?
O12 C10 C7' 114.9(8) . . ?
C10 O11 Zn2 133.6(5) . 2_565 ?
C10 O12 Zn1 132.0(5) . 2_565 ?
O23 C21 O22 126.4(6) . . ?
O23 C21 C24 117.3(6) . . ?
O22 C21 C24 116.3(5) . . ?
C21 O22 Zn2 136.7(4) . . ?
C21 O22 Zn1 114.1(4) . . ?
Zn2 O22 Zn1 106.32(18) . . ?
C21 O23 Zn1 130.3(5) . 4_556 ?
O25 C24 C26 112.0(6) . . ?
O25 C24 C21 110.6(5) . . ?
C26 C24 C21 108.1(6) . . ?
C24 O25 Zn2 117.9(4) . 4_456 ?
C24 O25 Zn1 115.4(4) . . ?
Zn2 O25 Zn1 126.0(2) 4_456 . ?
C30' O30 Zn2 132.4(15) . . ?
C30 O30 Zn2 127.0(11) . . ?
O30 C30 N31 129(2) . . ?
C30 N31 C32 120.0(18) . . ?
C30 N31 C33 125.3(18) . . ?
C32 N31 C33 114.7(17) . . ?
O30 C30' N31' 117(2) . . ?
C30' N31' C32' 125(2) . . ?
C30' N31' C33' 124(2) . . ?
C32' N31' C33' 111(2) . . ?

_refine_diff_density_max         0.425
_refine_diff_density_min         -0.798
_refine_diff_density_rms         0.091



#===END

