# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_CP
_database_code_depnum_ccdc_archive 'CCDC 1542144'
_audit_update_record             
;
2017-04-05 deposited with the CCDC.
2017-06-13 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 H16 N2 O4 Zn'
_chemical_formula_weight         389.70

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           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   6.7317(3)
_cell_length_b                   16.4136(5)
_cell_length_c                   14.9850(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1655.71(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6868
_cell_measurement_theta_min      3.27
_cell_measurement_theta_max      30.51

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    1.509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.729
_exptl_absorpt_correction_T_max  0.834
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6868
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         30.51
_reflns_number_total             2272
_reflns_number_gt                1791
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL-PLUS (Sheldrick, 1990)'
_computing_publication_material  SHELXL-97

_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)+(0.1000P)²+0.0000P] 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         2272
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1518
_refine_ls_wR_factor_gt          0.1391
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.458
_refine_ls_shift/su_mean         0.082

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 0.0000 0.35495(2) 0.2500 0.02966(18) Uani 1 2 d S . .
N1 N 0.1659(3) 0.25596(11) 0.29679(13) 0.0353(5) Uani 1 1 d . . .
C3 C 0.4573(3) 0.48000(14) 0.03857(17) 0.0329(5) Uani 1 1 d . . .
H3A H 0.5415 0.4571 0.0809 0.039 Uiso 1 1 calc R . .
C4 C 0.0939(4) 0.18204(14) 0.27559(16) 0.0358(5) Uani 1 1 d . . .
O3 O 0.2772(3) 0.40498(13) 0.18884(15) 0.0621(6) Uani 1 1 d . . .
C1 C 0.1680(4) 0.43103(12) 0.12820(17) 0.0377(6) Uani 1 1 d . . .
C5 C 0.3331(4) 0.26210(15) 0.34292(17) 0.0404(6) Uani 1 1 d . . .
H5A H 0.3811 0.3140 0.3555 0.048 Uiso 1 1 calc R . .
C8 C 0.1959(4) 0.11188(15) 0.3012(2) 0.0481(7) Uani 1 1 d . . .
H8A H 0.1487 0.0606 0.2853 0.058 Uiso 1 1 calc R . .
C2 C 0.2617(3) 0.47516(13) 0.05060(16) 0.0344(5) Uani 1 1 d . . .
H2A H 0.1789 0.5002 0.0092 0.041 Uiso 1 1 calc R . .
C6 C 0.4404(5) 0.19575(18) 0.37349(19) 0.0476(7) Uani 1 1 d . . .
C7 C 0.3674(4) 0.11973(16) 0.3503(2) 0.0533(8) Uani 1 1 d . . .
H7A H 0.4354 0.0732 0.3683 0.064 Uiso 1 1 calc R . .
C9 C 0.6249(4) 0.2071(2) 0.4291(2) 0.0602(8) Uani 1 1 d . . .
H9A H 0.6799 0.1548 0.4437 0.090 Uiso 1 1 calc R . .
H9B H 0.5916 0.2356 0.4830 0.090 Uiso 1 1 calc R . .
H9C H 0.7206 0.2382 0.3960 0.090 Uiso 1 1 calc R . .
O1 O -0.0138(2) 0.42257(12) 0.12931(17) 0.0477(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Zn1 0.0486(3) 0.0166(2) 0.0238(3) 0.000 0.00438(14) 0.000
N1 0.0560(12) 0.0205(9) 0.0294(10) 0.0018(8) 0.0094(9) 0.0034(8)
C3 0.0462(13) 0.0244(11) 0.0281(12) 0.0037(10) 0.0061(10) 0.0034(9)
C4 0.0580(15) 0.0216(10) 0.0280(11) 0.0029(10) 0.0153(11) 0.0028(10)
O3 0.0764(14) 0.0576(13) 0.0523(13) 0.0288(12) 0.0189(11) 0.0095(10)
C1 0.0605(17) 0.0193(10) 0.0333(13) -0.0012(10) 0.0168(12) 0.0029(10)
C5 0.0559(15) 0.0338(12) 0.0314(12) 0.0014(11) 0.0080(11) 0.0030(10)
C8 0.0756(18) 0.0214(11) 0.0474(16) 0.0067(12) 0.0138(15) 0.0052(11)
C2 0.0450(13) 0.0267(10) 0.0316(12) 0.0041(10) 0.0069(10) 0.0018(9)
C6 0.0595(15) 0.0497(16) 0.0336(14) 0.0150(13) 0.0109(13) 0.0092(14)
C7 0.0716(19) 0.0353(13) 0.0530(18) 0.0192(13) 0.0155(15) 0.0220(12)
C9 0.067(2) 0.069(2) 0.0443(16) 0.0164(16) 0.0027(14) 0.0125(15)
O1 0.0581(13) 0.0357(10) 0.0494(13) 0.0012(10) 0.0212(9) -0.0138(7)

_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 N1 2.0925(19) 3 ?
Zn1 N1 2.0925(19) . ?
Zn1 O1 2.124(2) 3 ?
Zn1 O1 2.124(2) . ?
Zn1 O3 2.2351(19) . ?
Zn1 O3 2.2351(19) 3 ?
Zn1 C1 2.484(2) 3 ?
Zn1 C1 2.484(2) . ?
N1 C5 1.324(3) . ?
N1 C4 1.345(3) . ?
C3 C2 1.331(3) . ?
C3 C3 1.448(5) 5_665 ?
C4 C8 1.394(3) . ?
C4 C4 1.479(6) 3 ?
O3 C1 1.245(3) . ?
C1 O1 1.232(3) . ?
C1 C2 1.508(3) . ?
C5 C6 1.385(4) . ?
C8 C7 1.376(4) . ?
C6 C7 1.385(4) . ?
C6 C9 1.507(5) . ?

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
N1 Zn1 N1 78.13(11) 3 . ?
N1 Zn1 O1 135.59(7) 3 3 ?
N1 Zn1 O1 95.57(8) . 3 ?
N1 Zn1 O1 95.57(8) 3 . ?
N1 Zn1 O1 135.59(7) . . ?
O1 Zn1 O1 116.99(12) 3 . ?
N1 Zn1 O3 126.40(8) 3 . ?
N1 Zn1 O3 88.69(7) . . ?
O1 Zn1 O3 96.93(8) 3 . ?
O1 Zn1 O3 59.69(7) . . ?
N1 Zn1 O3 88.69(7) 3 3 ?
N1 Zn1 O3 126.40(8) . 3 ?
O1 Zn1 O3 59.69(7) 3 3 ?
O1 Zn1 O3 96.93(8) . 3 ?
O3 Zn1 O3 136.88(11) . 3 ?
N1 Zn1 C1 113.18(8) 3 3 ?
N1 Zn1 C1 112.78(8) . 3 ?
O1 Zn1 C1 29.72(7) 3 3 ?
O1 Zn1 C1 110.06(7) . 3 ?
O3 Zn1 C1 119.77(8) . 3 ?
O3 Zn1 C1 29.99(8) 3 3 ?
N1 Zn1 C1 112.78(8) 3 . ?
N1 Zn1 C1 113.18(8) . . ?
O1 Zn1 C1 110.06(7) 3 . ?
O1 Zn1 C1 29.72(7) . . ?
O3 Zn1 C1 29.99(8) . . ?
O3 Zn1 C1 119.77(8) 3 . ?
C1 Zn1 C1 119.63(9) 3 . ?
C5 N1 C4 119.9(2) . . ?
C5 N1 Zn1 124.70(15) . . ?
C4 N1 Zn1 115.41(17) . . ?
C2 C3 C3 121.8(3) . 5_665 ?
N1 C4 C8 120.2(3) . . ?
N1 C4 C4 115.51(15) . 3 ?
C8 C4 C4 124.29(17) . 3 ?
C1 O3 Zn1 86.13(16) . . ?
O3 C1 O1 122.6(2) . . ?
O3 C1 C2 118.7(2) . . ?
O1 C1 C2 118.7(2) . . ?
O3 C1 Zn1 63.87(14) . . ?
O1 C1 Zn1 58.74(15) . . ?
C2 C1 Zn1 176.77(19) . . ?
N1 C5 C6 123.8(2) . . ?
C7 C8 C4 118.9(2) . . ?
C3 C2 C1 123.1(2) . . ?
C7 C6 C5 116.1(3) . . ?
C7 C6 C9 122.8(3) . . ?
C5 C6 C9 121.0(3) . . ?
C6 C7 C8 121.1(2) . . ?
C1 O1 Zn1 91.54(17) . . ?

_diffrn_measured_fraction_theta_max 0.895
_diffrn_reflns_theta_full        30.51
_diffrn_measured_fraction_theta_full 0.895
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.064
