# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1501246'
_audit_update_record             
;
2016-08-28 deposited with the CCDC.
2018-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ZJU-129
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H11 N O6 Zn'
_chemical_formula_weight         246.52

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'
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'

_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                   7.2283(4)
_cell_length_b                   10.4670(4)
_cell_length_c                   11.1858(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     846.30(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6485
_cell_measurement_theta_min      2.664
_cell_measurement_theta_max      26.054

_exptl_crystal_description       none
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.935
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.902
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8907
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.665
_diffrn_reflns_theta_max         26.095
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1666
_reflns_number_gt                1618
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.690
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0283P)²+0.0426P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.020(14)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1666
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0169
_refine_ls_R_factor_gt           0.0160
_refine_ls_wR_factor_ref         0.0433
_refine_ls_wR_factor_gt          0.0428
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.001
_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 0.62198(4) 0.57121(3) -0.45931(2) 0.02268(10) Uani 1 1 d . . . . .
H1 H -0.414(4) 0.120(3) -0.445(3) 0.019(10) Uiso 1 1 d . . . . .
O1 O 0.3039(3) 0.4593(2) -0.44677(16) 0.0369(5) Uani 1 1 d . . . . .
O1A O 0.6980(3) 0.3814(2) -0.4793(2) 0.0393(5) Uani 1 1 d . . . . .
H3 H 0.6519 0.3158 -0.4505 0.059 Uiso 1 1 d R U . . .
O1M O 0.1420(3) 0.12841(16) -0.12436(16) 0.0281(4) Uani 1 1 d . . . . .
O2 O 0.0230(3) 0.25614(18) 0.01573(15) 0.0289(4) Uani 1 1 d . . . . .
O20 O 0.4840(3) 0.53385(17) -0.30430(16) 0.0316(4) Uani 1 1 d . . . . .
N8 N -0.1815(3) 0.3914(2) -0.13872(18) 0.0262(5) Uani 1 1 d . . . . .
H2 H -0.1936 0.4684 -0.1666 0.031 Uiso 1 1 d R U . . .
H5 H -0.2978 0.3700 -0.1312 0.031 Uiso 1 1 d R U . . .
H6 H 0.778(5) 0.363(4) -0.509(4) 0.058(14) Uiso 1 1 d . . . . .
C2 C 0.2135(4) 0.4229(3) -0.2408(2) 0.0306(6) Uani 1 1 d . . . . .
H2A H 0.1566 0.4944 -0.1997 0.037 Uiso 1 1 calc R U . . .
H2B H 0.2884 0.3769 -0.1831 0.037 Uiso 1 1 calc R U . . .
C3 C 0.0625(4) 0.3347(2) -0.2865(2) 0.0260(6) Uani 1 1 d . . . . .
H3A H 0.1197 0.2616 -0.3249 0.031 Uiso 1 1 calc R U . . .
H3B H -0.0090 0.3797 -0.3467 0.031 Uiso 1 1 calc R U . . .
C4 C 0.0393(4) 0.2187(2) -0.0902(2) 0.0214(5) Uani 1 1 d . . . . .
C14 C -0.0689(3) 0.2870(2) -0.1892(2) 0.0215(5) Uani 1 1 d . . . . .
H14 H -0.1532 0.2248 -0.2256 0.026 Uiso 1 1 calc R U . . .
C19 C 0.3385(4) 0.4740(2) -0.3389(2) 0.0266(6) Uani 1 1 d . . . . .
O3 O -0.4662(3) 0.1525(2) -0.4134(2) 0.0335(5) Uani 1 1 d . . . . .
H4 H -0.4725 0.1156 -0.3351 0.050 Uiso 1 1 d R U . . .


_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 O1M 2.0359(18) 4_654 ?
Zn1 O20 2.0382(18) . ?
Zn1 O1A 2.074(2) . ?
Zn1 N8 2.090(2) 2_564 ?
Zn1 O2 2.1076(18) 2_564 ?
O1 C19 1.242(3) . ?
O1A H3 0.8283 . ?
O1A H6 0.69(4) . ?
O1M C4 1.261(3) . ?
O1M Zn1 2.0359(18) 4_644 ?
O2 C4 1.254(3) . ?
O2 Zn1 2.1076(18) 2_565 ?
O20 C19 1.284(3) . ?
N8 C14 1.475(3) . ?
N8 Zn1 2.090(2) 2_565 ?
N8 H2 0.8693 . ?
N8 H5 0.8739 . ?
C2 C19 1.519(3) . ?
C2 C3 1.519(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C14 1.529(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C14 1.533(3) . ?
C14 H14 0.9800 . ?
O3 H1 0.62(3) . ?
O3 H4 0.9587 . ?

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
O1M Zn1 O20 94.33(7) 4_654 . ?
O1M Zn1 O1A 96.27(8) 4_654 . ?
O20 Zn1 O1A 92.16(9) . . ?
O1M Zn1 N8 102.34(8) 4_654 2_564 ?
O20 Zn1 N8 162.51(8) . 2_564 ?
O1A Zn1 N8 91.22(9) . 2_564 ?
O1M Zn1 O2 103.03(7) 4_654 2_564 ?
O20 Zn1 O2 91.94(7) . 2_564 ?
O1A Zn1 O2 159.90(9) . 2_564 ?
N8 Zn1 O2 79.31(7) 2_564 2_564 ?
Zn1 O1A H3 130.2 . . ?
Zn1 O1A H6 122(4) . . ?
H3 O1A H6 107.1 . . ?
C4 O1M Zn1 125.07(16) . 4_644 ?
C4 O2 Zn1 116.12(15) . 2_565 ?
C19 O20 Zn1 103.78(15) . . ?
C14 N8 Zn1 113.15(15) . 2_565 ?
C14 N8 H2 127.2 . . ?
Zn1 N8 H2 101.1 2_565 . ?
C14 N8 H5 112.2 . . ?
Zn1 N8 H5 98.9 2_565 . ?
H2 N8 H5 100.1 . . ?
C19 C2 C3 113.5(2) . . ?
C19 C2 H2A 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C19 C2 H2B 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C2 C3 C14 113.9(2) . . ?
C2 C3 H3A 108.8 . . ?
C14 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
C14 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
O2 C4 O1M 125.2(2) . . ?
O2 C4 C14 119.3(2) . . ?
O1M C4 C14 115.5(2) . . ?
N8 C14 C3 111.92(19) . . ?
N8 C14 C4 110.50(19) . . ?
C3 C14 C4 110.48(19) . . ?
N8 C14 H14 107.9 . . ?
C3 C14 H14 107.9 . . ?
C4 C14 H14 107.9 . . ?
O1 C19 O20 121.2(2) . . ?
O1 C19 C2 122.6(2) . . ?
O20 C19 C2 116.2(2) . . ?
H1 O3 H4 108.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C19 C2 C3 C14 -177.7(2) . . . . ?
Zn1 O2 C4 O1M 169.59(19) 2_565 . . . ?
Zn1 O2 C4 C14 -9.2(3) 2_565 . . . ?
Zn1 O1M C4 O2 -27.3(4) 4_644 . . . ?
Zn1 O1M C4 C14 151.54(16) 4_644 . . . ?
Zn1 N8 C14 C3 -114.07(18) 2_565 . . . ?
Zn1 N8 C14 C4 9.5(2) 2_565 . . . ?
C2 C3 C14 N8 66.8(3) . . . . ?
C2 C3 C14 C4 -56.8(3) . . . . ?
O2 C4 C14 N8 -0.3(3) . . . . ?
O1M C4 C14 N8 -179.2(2) . . . . ?
O2 C4 C14 C3 124.1(2) . . . . ?
O1M C4 C14 C3 -54.8(3) . . . . ?
Zn1 O20 C19 O1 -4.9(3) . . . . ?
Zn1 O20 C19 C2 175.07(19) . . . . ?
C3 C2 C19 O1 9.6(4) . . . . ?
C3 C2 C19 O20 -170.3(2) . . . . ?

_refine_diff_density_max         0.262
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.044

_shelxl_version_number           2013-2

