# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_rt_a
_database_code_depnum_ccdc_archive 'CCDC 1876536'
loop_
_audit_author_name
_audit_author_address
'Li Li'
;Northeast Normal University
China
;
_audit_update_record             
;
2018-11-01 deposited with the CCDC.	2019-09-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 N O10 Zn'
_chemical_formula_weight         472.70

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1    '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1059(10)
_cell_length_b                   9.2243(10)
_cell_length_c                   13.2852(15)
_cell_angle_alpha                76.875(2)
_cell_angle_beta                 80.247(2)
_cell_angle_gamma                62.573(2)
_cell_volume                     961.88(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3649
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      26.06

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             484
_exptl_absorpt_coefficient_mu    1.335
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.677
_exptl_absorpt_correction_T_max  0.707
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6089
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         26.07
_reflns_number_total             3798
_reflns_number_gt                3468
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0718P)²+0.2881P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3798
_refine_ls_number_parameters     289
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.1082
_refine_ls_wR_factor_gt          0.1061
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.059
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.58516(3) 0.10687(3) 0.80447(2) 0.02725(12) Uani 1 1 d . . .
O1 O 0.4640(2) 0.1087(2) 0.69055(14) 0.0349(4) Uani 1 1 d . . .
O2 O 0.2998(2) 0.1291(2) 1.14521(14) 0.0356(4) Uani 1 1 d . . .
O3 O 0.4146(2) 0.2249(2) 0.90239(14) 0.0391(4) Uani 1 1 d . . .
O4 O 0.7452(2) 0.1850(2) 0.71697(14) 0.0385(4) Uani 1 1 d . . .
O5 O 0.5415(2) 0.2789(3) 0.57128(14) 0.0408(5) Uani 1 1 d . . .
O6 O 0.2207(3) 0.0426(2) 1.03131(17) 0.0441(5) Uani 1 1 d . . .
N1 N 0.2175(3) 0.5183(3) 0.21692(16) 0.0313(4) Uani 1 1 d . . .
O2W O 0.0462(3) 0.9358(3) 0.73060(19) 0.0521(5) Uani 1 1 d D . .
O1W O 0.2065(3) 0.0476(4) 0.8275(2) 0.0610(7) Uani 1 1 d D . .
O7 O 0.2999(3) 0.4326(3) 0.7749(2) 0.0755(9) Uani 1 1 d . . .
O3W O 0.3102(4) 0.7004(3) 0.6341(2) 0.0710(8) Uani 1 1 d D . .
C1 C 0.1436(3) 0.4271(3) 0.93619(17) 0.0243(5) Uani 1 1 d . . .
C2 C 0.2219(3) 0.1548(3) 1.06745(18) 0.0278(5) Uani 1 1 d . . .
C3 C -0.0290(3) 0.4080(3) 1.09133(18) 0.0261(5) Uani 1 1 d . . .
H3 H -0.0486 0.3463 1.1533 0.031 Uiso 1 1 calc R . .
C4 C 0.1134(3) 0.3341(3) 1.02841(17) 0.0238(4) Uani 1 1 d . . .
C5 C 0.2967(3) 0.3595(3) 0.8641(2) 0.0324(5) Uani 1 1 d . . .
C6 C 0.1501(3) 0.3892(3) 0.39448(19) 0.0340(5) Uani 1 1 d . . .
C7 C 0.4530(3) 0.2054(3) 0.60399(19) 0.0304(5) Uani 1 1 d . . .
C8 C 0.4394(3) 0.5044(3) 0.04605(19) 0.0314(5) Uani 1 1 d . . .
C9 C 0.3239(3) 0.2296(3) 0.53621(18) 0.0311(5) Uani 1 1 d . . .
C10 C 0.2649(3) 0.3682(3) 0.45967(19) 0.0320(5) Uani 1 1 d . . .
H10 H 0.3028 0.4483 0.4519 0.038 Uiso 1 1 calc R . .
C11 C 0.0918(3) 0.5359(4) 0.3092(2) 0.0394(6) Uani 1 1 d . . .
H11A H 0.0684 0.6347 0.3356 0.047 Uiso 1 1 calc R . .
H11B H -0.0108 0.5499 0.2869 0.047 Uiso 1 1 calc R . .
C12 C 0.3590(4) 0.3812(4) 0.2105(2) 0.0444(7) Uani 1 1 d . . .
H12 H 0.3819 0.2909 0.2641 0.053 Uiso 1 1 calc R . .
C13 C 0.2899(4) 0.6446(3) 0.0543(2) 0.0419(6) Uani 1 1 d . . .
H13 H 0.2633 0.7361 0.0014 0.050 Uiso 1 1 calc R . .
C14 C 0.2660(4) 0.1097(4) 0.5485(2) 0.0418(6) Uani 1 1 d . . .
H14 H 0.3040 0.0166 0.6000 0.050 Uiso 1 1 calc R . .
C15 C 0.1818(4) 0.6487(3) 0.1396(2) 0.0412(6) Uani 1 1 d . . .
H15 H 0.0820 0.7431 0.1442 0.049 Uiso 1 1 calc R . .
C16 C 0.0944(4) 0.2677(4) 0.4074(2) 0.0471(7) Uani 1 1 d . . .
H16 H 0.0178 0.2798 0.3640 0.057 Uiso 1 1 calc R . .
C17 C 0.4710(4) 0.3711(4) 0.1264(2) 0.0478(7) Uani 1 1 d . . .
H17 H 0.5689 0.2743 0.1232 0.057 Uiso 1 1 calc R . .
C18 C 0.1515(5) 0.1306(5) 0.4834(3) 0.0538(8) Uani 1 1 d . . .
H18 H 0.1130 0.0509 0.4914 0.065 Uiso 1 1 calc R . .
H2WA H 0.127(3) 0.868(4) 0.697(3) 0.081 Uiso 1 1 d D . .
H2WB H 0.095(4) 0.959(5) 0.769(3) 0.081 Uiso 1 1 d D . .
H1WA H 0.225(5) 0.041(6) 0.8886(12) 0.081 Uiso 1 1 d D . .
H3WA H 0.324(5) 0.602(2) 0.653(3) 0.081 Uiso 1 1 d D . .
H3WB H 0.355(5) 0.700(5) 0.5729(14) 0.081 Uiso 1 1 d D . .
H1WB H 0.280(4) 0.060(6) 0.785(2) 0.081 Uiso 1 1 d 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 O3 1.9212(17) . ?
Zn1 O2 1.9385(17) 2_657 ?
Zn1 O4 2.0020(18) . ?
Zn1 O1 2.0116(18) . ?
O1 C7 1.273(3) . ?
O2 C2 1.268(3) . ?
O2 Zn1 1.9385(17) 2_657 ?
O3 C5 1.274(3) . ?
O5 C7 1.244(3) . ?
O6 C2 1.241(3) . ?
N1 C12 1.333(4) . ?
N1 C15 1.341(3) . ?
N1 C11 1.511(3) . ?
O2W H2WA 0.850(10) . ?
O2W H2WB 0.851(10) . ?
O1W H1WA 0.841(10) . ?
O1W H1WB 0.832(10) . ?
O7 C5 1.226(3) . ?
O3W H3WA 0.842(10) . ?
O3W H3WB 0.845(10) . ?
C1 C4 1.392(3) . ?
C1 C3 1.396(3) 2_567 ?
C1 C5 1.506(3) . ?
C2 C4 1.504(3) . ?
C3 C4 1.386(3) . ?
C3 C1 1.396(3) 2_567 ?
C3 H3 0.9300 . ?
C6 C10 1.387(4) . ?
C6 C16 1.397(4) . ?
C6 C11 1.497(4) . ?
C7 C9 1.506(3) . ?
C8 C17 1.384(4) . ?
C8 C13 1.389(4) . ?
C8 C8 1.492(5) 2_665 ?
C9 C10 1.385(4) . ?
C9 C14 1.398(4) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C17 1.368(4) . ?
C12 H12 0.9300 . ?
C13 C15 1.364(4) . ?
C13 H13 0.9300 . ?
C14 C18 1.383(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C18 1.372(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

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
O3 Zn1 O2 113.20(8) . 2_657 ?
O3 Zn1 O4 125.33(8) . . ?
O2 Zn1 O4 109.40(8) 2_657 . ?
O3 Zn1 O1 105.24(8) . . ?
O2 Zn1 O1 100.83(8) 2_657 . ?
O4 Zn1 O1 98.58(7) . . ?
C7 O1 Zn1 121.56(16) . . ?
C2 O2 Zn1 110.01(15) . 2_657 ?
C5 O3 Zn1 115.93(16) . . ?
C12 N1 C15 120.1(2) . . ?
C12 N1 C11 122.8(2) . . ?
C15 N1 C11 117.1(2) . . ?
H2WA O2W H2WB 103(2) . . ?
H1WA O1W H1WB 112(2) . . ?
H3WA O3W H3WB 102(2) . . ?
C4 C1 C3 119.3(2) . 2_567 ?
C4 C1 C5 123.1(2) . . ?
C3 C1 C5 117.6(2) 2_567 . ?
O6 C2 O2 123.7(2) . . ?
O6 C2 C4 121.2(2) . . ?
O2 C2 C4 114.8(2) . . ?
C4 C3 C1 121.5(2) . 2_567 ?
C4 C3 H3 119.2 . . ?
C1 C3 H3 119.2 2_567 . ?
C3 C4 C1 119.2(2) . . ?
C3 C4 C2 115.1(2) . . ?
C1 C4 C2 125.7(2) . . ?
O7 C5 O3 124.8(2) . . ?
O7 C5 C1 119.7(2) . . ?
O3 C5 C1 115.4(2) . . ?
C10 C6 C16 118.7(2) . . ?
C10 C6 C11 120.8(2) . . ?
C16 C6 C11 120.4(2) . . ?
O5 C7 O1 125.1(2) . . ?
O5 C7 C9 118.2(2) . . ?
O1 C7 C9 116.7(2) . . ?
C17 C8 C13 117.3(2) . . ?
C17 C8 C8 121.0(3) . 2_665 ?
C13 C8 C8 121.8(3) . 2_665 ?
C10 C9 C14 119.5(2) . . ?
C10 C9 C7 120.4(2) . . ?
C14 C9 C7 120.0(2) . . ?
C9 C10 C6 121.0(2) . . ?
C9 C10 H10 119.5 . . ?
C6 C10 H10 119.5 . . ?
C6 C11 N1 112.6(2) . . ?
C6 C11 H11A 109.1 . . ?
N1 C11 H11A 109.1 . . ?
C6 C11 H11B 109.1 . . ?
N1 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
N1 C12 C17 121.1(3) . . ?
N1 C12 H12 119.5 . . ?
C17 C12 H12 119.5 . . ?
C15 C13 C8 120.3(2) . . ?
C15 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
C18 C14 C9 119.5(3) . . ?
C18 C14 H14 120.2 . . ?
C9 C14 H14 120.2 . . ?
N1 C15 C13 120.9(3) . . ?
N1 C15 H15 119.5 . . ?
C13 C15 H15 119.5 . . ?
C18 C16 C6 120.6(3) . . ?
C18 C16 H16 119.7 . . ?
C6 C16 H16 119.7 . . ?
C12 C17 C8 120.3(3) . . ?
C12 C17 H17 119.9 . . ?
C8 C17 H17 119.9 . . ?
C16 C18 C14 120.7(3) . . ?
C16 C18 H18 119.7 . . ?
C14 C18 H18 119.7 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.07
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.075
