# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_1
_database_code_depnum_ccdc_archive 'CCDC 1850764'
_audit_update_record             
;
2018-06-21 deposited with the CCDC.
2019-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 N2 O8 Zn'
_chemical_formula_weight         478.73

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           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.7736(12)
_cell_length_b                   14.1120(14)
_cell_length_c                   12.1366(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.364(2)
_cell_angle_gamma                90.00
_cell_volume                     1992.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1282
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      21.71

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             980
_exptl_absorpt_coefficient_mu    1.285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.687
_exptl_absorpt_correction_T_max  0.725
_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            11783
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_av_sigmaI/netI    0.0719
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         25.49
_reflns_number_total             3706
_reflns_number_gt                2497
_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)+(0.0575P)²+1.9162P] 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         3706
_refine_ls_number_parameters     292
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1384
_refine_ls_wR_factor_gt          0.1190
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2W O 0.7522(4) 0.1000(3) 0.1260(4) 0.0586(11) Uani 1 1 d D . .
Zn1 Zn 0.83248(5) 0.13745(4) 0.82703(5) 0.03086(19) Uani 1 1 d . . .
N1 N 0.4321(3) 0.3759(3) 0.4984(3) 0.0330(9) Uani 1 1 d . . .
O1 O 0.7100(3) 0.2283(2) 0.7331(3) 0.0396(8) Uani 1 1 d . . .
N2 N 0.8899(3) 0.0907(3) 0.7028(4) 0.0365(10) Uani 1 1 d . . .
C1 C 0.4102(4) 0.3847(4) 0.3684(4) 0.0387(12) Uani 1 1 d . . .
H1A H 0.4767 0.3615 0.3573 0.046 Uiso 1 1 calc R . .
H1B H 0.4004 0.4511 0.3458 0.046 Uiso 1 1 calc R . .
C2 C 0.9768(4) 0.0192(3) 0.5419(4) 0.0344(11) Uani 1 1 d . . .
C3 C 0.2681(5) 0.3440(4) 0.1626(5) 0.0518(15) Uani 1 1 d . . .
H3 H 0.3087 0.3836 0.1328 0.062 Uiso 1 1 calc R . .
C4 C 0.8817(5) 0.0774(4) 0.5037(4) 0.0519(16) Uani 1 1 d . . .
H4 H 0.8450 0.0941 0.4225 0.062 Uiso 1 1 calc R . .
C5 C 0.3050(4) 0.3304(3) 0.2858(4) 0.0333(11) Uani 1 1 d . . .
C6 C 0.9798(5) 0.0352(5) 0.7380(5) 0.0620(18) Uani 1 1 d . . .
H6 H 1.0146 0.0191 0.8195 0.074 Uiso 1 1 calc R . .
C7 C 0.1691(5) 0.2974(5) 0.0835(5) 0.0617(18) Uani 1 1 d . . .
H7 H 0.1444 0.3067 0.0007 0.074 Uiso 1 1 calc R . .
C8 C 0.1077(5) 0.2388(4) 0.1236(6) 0.0542(16) Uani 1 1 d . . .
C9 C 0.8408(5) 0.1108(4) 0.5851(5) 0.0535(16) Uani 1 1 d . . .
H9 H 0.7759 0.1493 0.5566 0.064 Uiso 1 1 calc R . .
C10 C 0.1479(6) 0.2239(5) 0.2455(6) 0.077(2) Uani 1 1 d . . .
H10 H 0.1090 0.1827 0.2754 0.092 Uiso 1 1 calc R . .
C11 C 1.0263(6) -0.0009(5) 0.6632(5) 0.0643(18) Uani 1 1 d . . .
H11 H 1.0914 -0.0390 0.6948 0.077 Uiso 1 1 calc R . .
C12 C 0.2453(5) 0.2694(5) 0.3242(5) 0.069(2) Uani 1 1 d . . .
H12 H 0.2710 0.2579 0.4067 0.082 Uiso 1 1 calc R . .
C13 C 0.4733(4) 0.3646(3) 0.7366(4) 0.0344(11) Uani 1 1 d . . .
H13 H 0.4873 0.3606 0.8180 0.041 Uiso 1 1 calc R . .
C14 C 0.5160(4) 0.3198(3) 0.5709(4) 0.0337(11) Uani 1 1 d . . .
H14 H 0.5591 0.2851 0.5393 0.040 Uiso 1 1 calc R . .
O2 O 0.6410(3) 0.2299(3) 0.8744(3) 0.0577(11) Uani 1 1 d . . .
C15 C 0.3665(4) 0.4264(3) 0.5404(4) 0.0341(11) Uani 1 1 d . . .
H15 H 0.3074 0.4641 0.4876 0.041 Uiso 1 1 calc R . .
C16 C 0.5400(4) 0.3124(3) 0.6923(4) 0.0305(10) Uani 1 1 d . . .
C17 C 0.3862(4) 0.4225(3) 0.6599(4) 0.0330(11) Uani 1 1 d . . .
C18 C 0.6381(4) 0.2509(3) 0.7756(4) 0.0374(11) Uani 1 1 d . . .
O3 O 0.3519(3) 0.4970(3) 0.8165(3) 0.0567(11) Uani 1 1 d . . .
C19 C 0.3183(4) 0.4878(3) 0.7065(5) 0.0374(12) Uani 1 1 d . . .
O4 O -0.0566(5) 0.1413(4) 0.0800(6) 0.115(2) Uani 1 1 d . . .
C20 C -0.0030(5) 0.1894(5) 0.0366(7) 0.0635(18) Uani 1 1 d . . .
O5 O 0.2343(3) 0.5285(2) 0.6244(3) 0.0392(8) Uani 1 1 d . . .
O6 O -0.0302(4) 0.2069(4) -0.0698(4) 0.0902(17) Uani 1 1 d . . .
O1W O 0.4606(5) 0.3838(3) 0.0296(5) 0.0905(16) Uani 1 1 d D . .
H2WA H 0.813(4) 0.108(5) 0.114(8) 0.136 Uiso 1 1 d D . .
H1WA H 0.477(7) 0.428(4) 0.083(5) 0.136 Uiso 1 1 d D . .
H1WB H 0.416(6) 0.412(5) -0.035(4) 0.136 Uiso 1 1 d D . .
H2WB H 0.745(6) 0.152(3) 0.159(7) 0.136 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 O6 1.948(5) 1_656 ?
Zn1 O5 1.962(3) 2_646 ?
Zn1 O1 1.980(3) . ?
Zn1 N2 2.040(4) . ?
N1 C14 1.331(6) . ?
N1 C15 1.350(6) . ?
N1 C1 1.490(5) . ?
O1 C18 1.266(6) . ?
N2 C6 1.307(7) . ?
N2 C9 1.332(6) . ?
C1 C5 1.513(6) . ?
C2 C11 1.371(7) . ?
C2 C4 1.378(7) . ?
C2 C2 1.476(9) 3_756 ?
C3 C5 1.383(7) . ?
C3 C7 1.397(8) . ?
C4 C9 1.377(7) . ?
C5 C12 1.354(7) . ?
C6 C11 1.371(7) . ?
C7 C8 1.360(8) . ?
C8 C10 1.367(8) . ?
C8 C20 1.539(8) . ?
C10 C12 1.376(8) . ?
C13 C17 1.384(6) . ?
C13 C16 1.391(6) . ?
C14 C16 1.380(6) . ?
O2 C18 1.221(6) . ?
C15 C17 1.366(6) . ?
C16 C18 1.517(6) . ?
C17 C19 1.526(7) . ?
O3 C19 1.229(6) . ?
C19 O5 1.262(5) . ?
O4 C20 1.226(9) . ?
C20 O6 1.216(8) . ?
O5 Zn1 1.962(3) 2_656 ?
O6 Zn1 1.948(4) 1_454 ?

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
O6 Zn1 O5 126.0(2) 1_656 2_646 ?
O6 Zn1 O1 109.46(19) 1_656 . ?
O5 Zn1 O1 109.98(14) 2_646 . ?
O6 Zn1 N2 97.75(18) 1_656 . ?
O5 Zn1 N2 107.59(15) 2_646 . ?
O1 Zn1 N2 102.92(15) . . ?
C14 N1 C15 121.4(4) . . ?
C14 N1 C1 119.9(4) . . ?
C15 N1 C1 118.8(4) . . ?
C18 O1 Zn1 117.6(3) . . ?
C6 N2 C9 116.1(4) . . ?
C6 N2 Zn1 119.2(3) . . ?
C9 N2 Zn1 124.7(3) . . ?
N1 C1 C5 112.7(4) . . ?
C11 C2 C4 115.9(4) . . ?
C11 C2 C2 121.7(5) . 3_756 ?
C4 C2 C2 122.4(5) . 3_756 ?
C5 C3 C7 119.0(5) . . ?
C9 C4 C2 120.3(5) . . ?
C12 C5 C3 118.2(5) . . ?
C12 C5 C1 124.5(4) . . ?
C3 C5 C1 117.3(5) . . ?
N2 C6 C11 124.6(5) . . ?
C8 C7 C3 122.2(5) . . ?
C7 C8 C10 117.8(5) . . ?
C7 C8 C20 122.1(6) . . ?
C10 C8 C20 120.1(6) . . ?
N2 C9 C4 123.1(5) . . ?
C8 C10 C12 120.5(6) . . ?
C6 C11 C2 120.0(5) . . ?
C5 C12 C10 122.3(5) . . ?
C17 C13 C16 120.1(4) . . ?
N1 C14 C16 120.9(4) . . ?
N1 C15 C17 120.5(4) . . ?
C14 C16 C13 118.1(4) . . ?
C14 C16 C18 120.9(4) . . ?
C13 C16 C18 121.0(4) . . ?
C15 C17 C13 118.9(4) . . ?
C15 C17 C19 119.0(4) . . ?
C13 C17 C19 121.9(4) . . ?
O2 C18 O1 127.3(5) . . ?
O2 C18 C16 118.4(4) . . ?
O1 C18 C16 114.3(4) . . ?
O3 C19 O5 127.7(5) . . ?
O3 C19 C17 118.0(4) . . ?
O5 C19 C17 114.3(4) . . ?
O6 C20 O4 127.0(7) . . ?
O6 C20 C8 114.6(7) . . ?
O4 C20 C8 118.3(7) . . ?
C19 O5 Zn1 117.0(3) . 2_656 ?
C20 O6 Zn1 111.6(5) . 1_454 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.908
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.089
