# 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_djp-h2l-zn-dma-final
_database_code_depnum_ccdc_archive 'CCDC 1950609'
loop_
_audit_author_name
_audit_author_address
'jianpeng dong'
;nanyang normal university
China
;
_audit_update_record             
;
2019-08-31 deposited with the CCDC.	2019-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 N O6 Zn'
_chemical_formula_weight         342.60

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.0839(6)
_cell_length_b                   16.4996(10)
_cell_length_c                   7.0477(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.834(5)
_cell_angle_gamma                90
_cell_volume                     1261.49(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5890
_cell_measurement_theta_min      3.8250
_cell_measurement_theta_max      27.2220

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.804
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    1.976
_shelx_estimated_absorpt_T_min   0.693
_shelx_estimated_absorpt_T_max   0.743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.59298
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13358
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.201
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2224
_reflns_number_gt                1976
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.2000P)²+0.9216P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2224
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0632
_refine_ls_wR_factor_ref         0.2511
_refine_ls_wR_factor_gt          0.2446
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_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 0.92166(6) 0.86212(4) 0.48892(10) 0.0251(4) Uani 1 1 d . . . . .
O4 O 0.7706(4) 0.8173(3) 0.5534(6) 0.0280(10) Uani 1 1 d . . . . .
O2 O 0.8671(4) 0.5524(3) 0.7945(6) 0.0320(11) Uani 1 1 d . . . . .
O3 O 0.8842(4) 0.7184(3) 0.7098(8) 0.0404(13) Uani 1 1 d . . . . .
N1 N 0.0945(4) 0.8151(3) 0.5198(7) 0.0242(12) Uani 1 1 d . . . . .
O1 O 0.7979(5) 0.5367(3) 0.4782(7) 0.0431(13) Uani 1 1 d . . . . .
O1W O 0.9602(5) 0.9386(3) 0.7256(8) 0.0462(14) Uani 1 1 d . . . . .
H1WA H 1.021395 0.965861 0.720795 0.069 Uiso 1 1 d R U . . .
H1WB H 0.949325 0.939821 0.841475 0.069 Uiso 1 1 d R U . . .
C13 C 0.7836(5) 0.7483(4) 0.6287(8) 0.0222(13) Uani 1 1 d . . . . .
C7 C 0.3260(5) 0.7382(4) 0.5786(8) 0.0198(12) Uani 1 1 d . . . . .
C12 C 0.7892(5) 0.5663(4) 0.6347(9) 0.0247(13) Uani 1 1 d . . . . .
C1 C 0.6687(5) 0.6992(4) 0.6215(8) 0.0193(12) Uani 1 1 d . . . . .
C5 C 0.4471(5) 0.6971(4) 0.6088(8) 0.0212(12) Uani 1 1 d . . . . .
C2 C 0.6747(5) 0.6141(4) 0.6405(8) 0.0230(13) Uani 1 1 d . . . . .
C10 C 0.1056(5) 0.7348(4) 0.5114(9) 0.0265(13) Uani 1 1 d . . . . .
H10 H 0.033910 0.703894 0.485015 0.032 Uiso 1 1 calc R U . . .
C11 C 0.2165(5) 0.6951(4) 0.5393(9) 0.0260(13) Uani 1 1 d . . . . .
H11 H 0.218215 0.638863 0.531782 0.031 Uiso 1 1 calc R U . . .
C6 C 0.5558(5) 0.7386(4) 0.5997(8) 0.0209(12) Uani 1 1 d . . . . .
H6 H 0.552460 0.794295 0.578328 0.025 Uiso 1 1 calc R U . . .
C9 C 0.1998(6) 0.8578(4) 0.5558(10) 0.0244(14) Uani 1 1 d . . . . .
H9 H 0.194814 0.913915 0.562532 0.029 Uiso 1 1 calc R U . . .
C8 C 0.3139(5) 0.8229(4) 0.5829(9) 0.0260(13) Uani 1 1 d . . . . .
H8 H 0.383872 0.855486 0.604261 0.031 Uiso 1 1 calc R U . . .
C4 C 0.4564(6) 0.6130(4) 0.6392(9) 0.0292(14) Uani 1 1 d . . . . .
H4 H 0.386456 0.583515 0.649106 0.035 Uiso 1 1 calc R U . . .
C3 C 0.5680(6) 0.5734(4) 0.6548(10) 0.0305(14) Uani 1 1 d . . . . .
H3 H 0.571359 0.517700 0.675512 0.037 Uiso 1 1 calc R U . . .
O2W O 0.5973(9) 0.5503(6) 0.1263(15) 0.112(3) Uiso 1 1 d . . . . .
H2WA H 0.638512 0.554420 0.236600 0.168 Uiso 1 1 d R U . . .
H2WB H 0.641372 0.575880 0.058900 0.168 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 O4 1.967(4) . ?
ZN1 O2 1.973(4) 4_575 ?
ZN1 N1 2.036(5) 1_655 ?
ZN1 O1W 2.065(5) . ?
ZN1 O3 2.340(5) 4_575 ?
O4 C13 1.253(7) . ?
O2 C12 1.291(8) . ?
O2 ZN1 1.973(4) 4_576 ?
O3 C13 1.245(7) . ?
O3 ZN1 2.340(5) 4_576 ?
N1 C10 1.333(9) . ?
N1 C9 1.342(8) . ?
N1 ZN1 2.036(5) 1_455 ?
O1 C12 1.228(8) . ?
O1W H1WA 0.8201 . ?
O1W H1WB 0.8500 . ?
C13 C1 1.501(8) . ?
C7 C11 1.385(8) . ?
C7 C8 1.405(9) . ?
C7 C5 1.480(8) . ?
C12 C2 1.502(8) . ?
C1 C6 1.391(8) . ?
C1 C2 1.410(8) . ?
C5 C6 1.399(8) . ?
C5 C4 1.404(9) . ?
C2 C3 1.381(9) . ?
C10 C11 1.371(8) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C6 H6 0.9300 . ?
C9 C8 1.366(9) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C4 C3 1.384(9) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
O2W H2WA 0.8200 . ?
O2W H2WB 0.8591 . ?

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
O4 ZN1 O2 105.95(18) . 4_575 ?
O4 ZN1 N1 131.2(2) . 1_655 ?
O2 ZN1 N1 119.6(2) 4_575 1_655 ?
O4 ZN1 O1W 95.04(19) . . ?
O2 ZN1 O1W 96.2(2) 4_575 . ?
N1 ZN1 O1W 96.4(2) 1_655 . ?
O4 ZN1 O3 88.18(17) . 4_575 ?
O2 ZN1 O3 81.12(19) 4_575 4_575 ?
N1 ZN1 O3 82.79(17) 1_655 4_575 ?
O1W ZN1 O3 176.29(19) . 4_575 ?
C13 O4 ZN1 114.2(4) . . ?
C12 O2 ZN1 122.2(4) . 4_576 ?
C13 O3 ZN1 126.7(4) . 4_576 ?
C10 N1 C9 116.4(5) . . ?
C10 N1 ZN1 117.9(4) . 1_455 ?
C9 N1 ZN1 125.7(4) . 1_455 ?
ZN1 O1W H1WA 109.8 . . ?
ZN1 O1W H1WB 138.1 . . ?
H1WA O1W H1WB 108.0 . . ?
O3 C13 O4 124.7(5) . . ?
O3 C13 C1 118.4(5) . . ?
O4 C13 C1 116.9(5) . . ?
C11 C7 C8 115.6(5) . . ?
C11 C7 C5 121.6(5) . . ?
C8 C7 C5 122.7(5) . . ?
O1 C12 O2 123.4(6) . . ?
O1 C12 C2 117.1(6) . . ?
O2 C12 C2 119.2(5) . . ?
C6 C1 C2 120.0(5) . . ?
C6 C1 C13 119.3(5) . . ?
C2 C1 C13 120.7(5) . . ?
C6 C5 C4 117.0(5) . . ?
C6 C5 C7 122.2(5) . . ?
C4 C5 C7 120.7(5) . . ?
C3 C2 C1 117.8(5) . . ?
C3 C2 C12 119.2(6) . . ?
C1 C2 C12 122.9(5) . . ?
N1 C10 C11 123.8(6) . . ?
N1 C10 H10 118.1 . . ?
C11 C10 H10 118.1 . . ?
C10 C11 C7 120.4(6) . . ?
C10 C11 H11 119.8 . . ?
C7 C11 H11 119.8 . . ?
C1 C6 C5 122.0(5) . . ?
C1 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
N1 C9 C8 123.4(5) . . ?
N1 C9 H9 118.3 . . ?
C8 C9 H9 118.3 . . ?
C9 C8 C7 120.3(5) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C3 C4 C5 121.0(6) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C2 C3 C4 121.9(6) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
H2WA O2W H2WB 102.3 . . ?

_refine_diff_density_max         1.845
_refine_diff_density_min         -0.893
_refine_diff_density_rms         0.129

