# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_ydkr
_database_code_depnum_ccdc_archive 'CCDC 1564018'
loop_
_audit_author_name
_audit_author_address
'Rika Ochi'
;Hokkaido Univ.
Japan
;
_audit_update_record             
;
2019-02-19 deposited with the CCDC.	2019-02-20 downloaded from the CCDC.
;
_audit_creation_date             2019-02-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H10 N2 O6 Zn'
_chemical_formula_sum            'C10 H10 N2 O6 Zn'
_chemical_formula_weight         319.57
_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'
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.9070(5)
_cell_length_b                   15.2244(8)
_cell_length_c                   10.2954(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.868(2)
_cell_angle_gamma                90
_cell_volume                     1238.69(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2814
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      27.432
_cell_measurement_theta_min      3.329
_shelx_estimated_absorpt_T_max   0.856
_shelx_estimated_absorpt_T_min   0.690
_exptl_absorpt_coefficient_mu    2.007
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCORE(Higashi  1995)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11485
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.432
_diffrn_reflns_theta_min         3.329
_diffrn_ambient_temperature      173.15
_diffrn_detector                 'Rigaku curved IP area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'Imaging plate area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku RAPID FR'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              FR
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2431
_reflns_number_total             2811
_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       RAPID-AUTO
_computing_data_collection       RAPID-AUTO
_computing_data_reduction        RAPID-AUTO
_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    
;
SIR2004 (Burla, et al., 2005)
;
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2811
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0259
_refine_ls_restrained_S_all      1.101
_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)+(0.0355P)²+0.5852P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0644
_refine_ls_wR_factor_ref         0.0703
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C10(H10), C3(H3)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_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 0.90025(3) 0.57734(2) 0.59053(2) 0.01404(8) Uani 1 1 d . . . . .
O1 O 1.06197(16) 0.55733(8) 0.43381(13) 0.0141(3) Uani 1 1 d . . . . .
O2 O 0.67387(17) 0.59659(9) 0.51152(15) 0.0212(3) Uani 1 1 d . . . . .
O3 O 0.74345(18) 0.71515(10) 0.39531(18) 0.0306(4) Uani 1 1 d . . . . .
C6 C 0.6419(2) 0.66123(12) 0.4358(2) 0.0171(4) Uani 1 1 d . . . . .
C2 C 0.4566(2) 0.67074(12) 0.39380(19) 0.0153(4) Uani 1 1 d . . . . .
C4 C 0.2290(2) 0.75029(12) 0.28560(19) 0.0155(4) Uani 1 1 d . . . . .
O4 O 1.01154(18) 0.68474(9) 0.65713(15) 0.0230(3) Uani 1 1 d . . . . .
O6 O 0.8163(2) 0.53597(10) 0.77018(15) 0.0280(3) Uani 1 1 d . . . . .
C1 C 0.3406(2) 0.60830(12) 0.43220(18) 0.0149(4) Uani 1 1 d . . . . .
H1 H 0.376920 0.559349 0.483088 0.018 Uiso 1 1 calc R . . . .
C5 C 0.1178(2) 0.68631(12) 0.32512(19) 0.0147(4) Uani 1 1 d . . . . .
H5 H 0.000769 0.690590 0.301999 0.018 Uiso 1 1 calc R . . . .
C10 C 0.8145(3) 0.57805(14) 0.8736(2) 0.0259(5) Uani 1 1 d . . . . .
H10 H 0.845343 0.638352 0.872793 0.031 Uiso 1 1 calc R . . . .
N2 N 0.7714(3) 0.54228(14) 0.98442(19) 0.0304(4) Uani 1 1 d . . . . .
C7 C 0.1589(2) 0.82838(12) 0.20995(19) 0.0176(4) Uani 1 1 d . . . . .
N1 N 1.17604(18) 0.61765(10) 0.39675(15) 0.0126(3) Uani 1 1 d . . . . .
C8 C 0.7225(4) 0.44973(19) 0.9885(3) 0.0441(7) Uani 1 1 d . . . . .
H8A H 0.660842 0.434191 0.907595 0.066 Uiso 1 1 calc GR . . . .
H8B H 0.649793 0.439788 1.062308 0.066 Uiso 1 1 calc GR . . . .
H8C H 0.824179 0.413176 0.998153 0.066 Uiso 1 1 calc GR . . . .
C9 C 0.7766(4) 0.5917(2) 1.1070(3) 0.0485(7) Uani 1 1 d . . . . .
H9A H 0.813274 0.652075 1.090701 0.073 Uiso 1 1 calc GR . . . .
H9B H 0.856403 0.563563 1.168817 0.073 Uiso 1 1 calc GR . . . .
H9C H 0.663560 0.592427 1.143301 0.073 Uiso 1 1 calc GR . . . .
O5 O 0.2416(2) 0.89653(10) 0.20641(16) 0.0267(3) Uani 1 1 d . . . . .
C3 C 0.4011(2) 0.74296(12) 0.31993(19) 0.0163(4) Uani 1 1 d . . . . .
H3 H 0.479162 0.786365 0.293473 0.020 Uiso 1 1 calc R . . . .


_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 O1 2.0881(13) 3_766 ?
Zn1 O1 2.1132(14) . ?
Zn1 O2 1.9638(14) . ?
Zn1 O4 1.9694(14) . ?
Zn1 O6 2.0828(16) . ?
O1 N1 1.3509(19) . ?
O2 C6 1.276(2) . ?
O3 C6 1.231(2) . ?
C6 C2 1.521(2) . ?
C2 C1 1.387(3) . ?
C2 C3 1.399(3) . ?
C4 C5 1.382(3) . ?
C4 C7 1.516(3) . ?
C4 C3 1.400(3) . ?
O4 C7 1.285(2) 4_676 ?
O6 C10 1.243(3) . ?
C1 N1 1.348(2) 1_455 ?
C5 N1 1.352(2) 1_455 ?
C10 N2 1.319(3) . ?
N2 C8 1.462(3) . ?
N2 C9 1.469(3) . ?
C7 O5 1.228(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
O1 Zn1 O1 70.99(6) 3_766 . ?
O2 Zn1 O1 103.23(6) . 3_766 ?
O2 Zn1 O1 105.74(6) . . ?
O2 Zn1 O4 114.28(6) . . ?
O2 Zn1 O6 95.76(6) . . ?
O4 Zn1 O1 96.37(6) . . ?
O4 Zn1 O1 142.46(6) . 3_766 ?
O4 Zn1 O6 95.37(6) . . ?
O6 Zn1 O1 148.51(6) . . ?
O6 Zn1 O1 81.99(6) . 3_766 ?
Zn1 O1 Zn1 109.01(6) 3_766 . ?
N1 O1 Zn1 122.94(11) . . ?
N1 O1 Zn1 122.29(11) . 3_766 ?
C6 O2 Zn1 121.89(13) . . ?
O2 C6 C2 114.67(16) . . ?
O3 C6 O2 127.07(18) . . ?
O3 C6 C2 118.27(17) . . ?
C1 C2 C6 119.56(17) . . ?
C1 C2 C3 119.66(17) . . ?
C3 C2 C6 120.75(17) . . ?
C5 C4 C7 118.59(16) . . ?
C5 C4 C3 119.48(17) . . ?
C3 C4 C7 121.89(17) . . ?
C7 O4 Zn1 114.01(12) 4_676 . ?
C10 O6 Zn1 128.15(15) . . ?
N1 C1 C2 119.47(17) 1_455 . ?
N1 C5 C4 119.79(16) 1_455 . ?
O6 C10 N2 122.6(2) . . ?
C10 N2 C8 119.9(2) . . ?
C10 N2 C9 122.1(2) . . ?
C8 N2 C9 118.0(2) . . ?
O4 C7 C4 113.98(16) 4_475 . ?
O5 C7 C4 119.47(18) . . ?
O5 C7 O4 126.52(18) . 4_475 ?
O1 N1 C5 117.46(15) . 1_655 ?
C1 N1 O1 119.96(15) 1_655 . ?
C1 N1 C5 122.58(16) 1_655 1_655 ?
C2 C3 C4 119.01(17) . . ?

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
Zn1 O1 N1 C1 101.09(17) . . . 1_655 ?
Zn1 O1 N1 C1 -49.2(2) 3_766 . . 1_655 ?
Zn1 O1 N1 C5 -78.42(18) . . . 1_655 ?
Zn1 O1 N1 C5 131.30(14) 3_766 . . 1_655 ?
Zn1 O2 C6 O3 5.1(3) . . . . ?
Zn1 O2 C6 C2 -174.52(12) . . . . ?
Zn1 O6 C10 N2 -174.05(16) . . . . ?
O2 C6 C2 C1 -3.8(3) . . . . ?
O2 C6 C2 C3 174.48(18) . . . . ?
O3 C6 C2 C1 176.58(19) . . . . ?
O3 C6 C2 C3 -5.2(3) . . . . ?
C6 C2 C1 N1 178.87(17) . . . 1_455 ?
C6 C2 C3 C4 -178.63(17) . . . . ?
O6 C10 N2 C8 -0.3(4) . . . . ?
O6 C10 N2 C9 177.4(2) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C5 C4 C7 O4 -19.5(3) . . . 4_475 ?
C5 C4 C7 O5 158.95(19) . . . . ?
C5 C4 C3 C2 0.0(3) . . . . ?
C7 C4 C5 N1 -177.59(17) . . . 1_455 ?
C7 C4 C3 C2 177.74(18) . . . . ?
C3 C2 C1 N1 0.6(3) . . . 1_455 ?
C3 C4 C5 N1 0.3(3) . . . 1_455 ?
C3 C4 C7 O4 162.67(19) . . . 4_475 ?
C3 C4 C7 O5 -18.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
