# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_zl_sq
_database_code_depnum_ccdc_archive 'CCDC 1505622'
_audit_update_record             
;
2016-09-21 deposited with the CCDC.
2016-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ZJU-198
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H7 N O4 Zn'
_chemical_formula_weight         294.56

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   7.1952(5)
_cell_length_b                   19.7441(16)
_cell_length_c                   20.4254(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2901.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6325
_cell_measurement_theta_min      2.872
_cell_measurement_theta_max      25.199

_exptl_crystal_description       no
_exptl_crystal_colour            transparent
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.696
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23793
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.994
_diffrn_reflns_theta_max         26.171
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2855
_reflns_number_gt                1973
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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-2013 (Sheldrick, 2013)'
_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)+(0.0973P)²+15.8809P]
 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         2855
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1194
_refine_ls_R_factor_gt           0.0893
_refine_ls_wR_factor_ref         0.2188
_refine_ls_wR_factor_gt          0.2027
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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_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 0.09075(13) 0.18557(4) 0.55698(3) 0.0411(3) Uani 1 1 d . . . . .
O1A O 0.0376(7) 0.1785(3) 0.4616(2) 0.0409(12) Uani 1 1 d . . . . .
O3 O -0.1902(7) 0.2542(3) 0.4618(2) 0.0448(13) Uani 1 1 d . . . . .
O13 O 0.3147(17) -0.1394(4) 0.1693(5) 0.128(4) Uani 1 1 d . . . . .
O18 O 0.2991(14) -0.0956(4) 0.0737(4) 0.103(3) Uani 1 1 d . . . . .
C41 C 0.1346(13) 0.0237(5) 0.1301(4) 0.059(2) Uani 1 1 d . . . . .
H36 H 0.1232 0.0236 0.0841 0.088 Uiso 1 1 d R U . . .
N9 N -0.1110(8) 0.2572(3) 0.1030(3) 0.0411(14) Uani 1 1 d . . . . .
C4 C 0.0060(9) 0.1664(4) 0.3249(3) 0.0323(15) Uani 1 1 d . . . . .
H4 H 0.0741 0.1347 0.3485 0.039 Uiso 1 1 calc R U . . .
C5 C -0.0519(8) 0.2026(4) 0.1454(3) 0.0324(15) Uani 1 1 d . . . . .
C6 C -0.0779(9) 0.2156(4) 0.4318(3) 0.0348(15) Uani 1 1 d . . . . .
C6A C 0.0640(10) 0.0888(4) 0.1588(3) 0.0440(18) Uani 1 1 d . . . . .
C7 C 0.0039(11) 0.1404(4) 0.1182(3) 0.0440(18) Uani 1 1 d . . . . .
H7 H 0.0004 0.1340 0.0731 0.053 Uiso 1 1 calc R U . . .
C8 C 0.2767(16) -0.0914(6) 0.1330(6) 0.076(3) Uani 1 1 d . . . . .
C10 C 0.0629(10) 0.0986(4) 0.2261(3) 0.0420(17) Uani 1 1 d . . . . .
H10 H 0.1017 0.0636 0.2533 0.050 Uiso 1 1 calc R U . . .
C12 C 0.2014(16) -0.0270(5) 0.1622(5) 0.076(3) Uani 1 1 d . . . . .
H12 H 0.2032 -0.0234 0.2076 0.092 Uiso 1 1 calc R U . . .
C13 C 0.0056(9) 0.1590(4) 0.2536(3) 0.0352(15) Uani 1 1 d . . . . .
C15A C -0.0812(9) 0.2138(4) 0.3592(3) 0.0376(16) Uani 1 1 d . . . . .
H15A H -0.1468 0.2471 0.3369 0.045 Uiso 1 1 calc R U . . .
C25 C -0.0496(8) 0.2118(4) 0.2121(3) 0.0306(14) Uani 1 1 d . . . . .
H25 H -0.0849 0.2533 0.2298 0.037 Uiso 1 1 calc 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 O18 1.975(8) 2 ?
Zn1 O1A 1.990(5) . ?
Zn1 O3 2.011(5) 3_556 ?
Zn1 N9 2.066(6) 8_566 ?
O1A C6 1.265(8) . ?
O3 C6 1.269(8) . ?
O3 Zn1 2.011(5) 3_456 ?
O13 C8 1.232(13) . ?
O18 C8 1.225(12) . ?
O18 Zn1 1.975(8) 2_554 ?
C41 C12 1.290(13) . ?
C41 C6A 1.500(11) . ?
C41 H36 0.9431 . ?
N9 C5 1.446(9) . ?
N9 Zn1 2.066(6) 8_565 ?
C4 C15A 1.326(10) . ?
C4 C13 1.464(9) . ?
C4 H4 0.9300 . ?
C5 C25 1.375(8) . ?
C5 C7 1.406(10) . ?
C6 C15A 1.483(8) . ?
C6A C7 1.384(11) . ?
C6A C10 1.388(10) . ?
C7 H7 0.9300 . ?
C8 C12 1.507(14) . ?
C10 C13 1.382(10) . ?
C10 H10 0.9300 . ?
C12 H12 0.9300 . ?
C13 C25 1.401(10) . ?
C15A H15A 0.9300 . ?
C25 H25 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
O18 Zn1 O1A 100.6(3) 2 . ?
O18 Zn1 O3 104.5(3) 2 3_556 ?
O1A Zn1 O3 90.3(2) . 3_556 ?
O18 Zn1 N9 134.0(3) 2 8_566 ?
O1A Zn1 N9 110.4(2) . 8_566 ?
O3 Zn1 N9 108.3(2) 3_556 8_566 ?
C6 O1A Zn1 123.8(4) . . ?
C6 O3 Zn1 139.6(4) . 3_456 ?
C8 O18 Zn1 106.5(8) . 2_554 ?
C12 C41 C6A 126.3(8) . . ?
C12 C41 H36 122.4 . . ?
C6A C41 H36 111.3 . . ?
C5 N9 Zn1 118.3(4) . 8_565 ?
C15A C4 C13 126.5(6) . . ?
C15A C4 H4 116.7 . . ?
C13 C4 H4 116.7 . . ?
C25 C5 C7 120.2(7) . . ?
C25 C5 N9 119.8(6) . . ?
C7 C5 N9 119.9(6) . . ?
O1A C6 O3 122.3(6) . . ?
O1A C6 C15A 118.5(6) . . ?
O3 C6 C15A 119.2(6) . . ?
C7 C6A C10 119.3(7) . . ?
C7 C6A C41 120.2(7) . . ?
C10 C6A C41 120.5(7) . . ?
C6A C7 C5 119.7(6) . . ?
C6A C7 H7 120.1 . . ?
C5 C7 H7 120.1 . . ?
O18 C8 O13 120.9(11) . . ?
O18 C8 C12 119.7(11) . . ?
O13 C8 C12 119.4(10) . . ?
C13 C10 C6A 121.7(7) . . ?
C13 C10 H10 119.2 . . ?
C6A C10 H10 119.2 . . ?
C41 C12 C8 126.0(10) . . ?
C41 C12 H12 117.0 . . ?
C8 C12 H12 117.0 . . ?
C10 C13 C25 118.7(6) . . ?
C10 C13 C4 119.4(7) . . ?
C25 C13 C4 121.9(6) . . ?
C4 C15A C6 122.6(7) . . ?
C4 C15A H15A 118.7 . . ?
C6 C15A H15A 118.7 . . ?
C5 C25 C13 120.3(7) . . ?
C5 C25 H25 119.9 . . ?
C13 C25 H25 119.9 . . ?

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 N9 C5 C25 100.2(6) 8_565 . . . ?
Zn1 N9 C5 C7 -79.5(7) 8_565 . . . ?
Zn1 O1A C6 O3 -10.5(10) . . . . ?
Zn1 O1A C6 C15A 169.4(5) . . . . ?
Zn1 O3 C6 O1A -172.4(5) 3_456 . . . ?
Zn1 O3 C6 C15A 7.7(12) 3_456 . . . ?
C12 C41 C6A C7 177.0(10) . . . . ?
C12 C41 C6A C10 -1.3(14) . . . . ?
C10 C6A C7 C5 1.9(11) . . . . ?
C41 C6A C7 C5 -176.3(7) . . . . ?
C25 C5 C7 C6A -1.0(10) . . . . ?
N9 C5 C7 C6A 178.6(6) . . . . ?
Zn1 O18 C8 O13 -2.6(16) 2_554 . . . ?
Zn1 O18 C8 C12 177.5(8) 2_554 . . . ?
C7 C6A C10 C13 -0.9(11) . . . . ?
C41 C6A C10 C13 177.4(7) . . . . ?
C6A C41 C12 C8 -178.3(9) . . . . ?
O18 C8 C12 C41 9.0(19) . . . . ?
O13 C8 C12 C41 -170.9(12) . . . . ?
C6A C10 C13 C25 -1.1(11) . . . . ?
C6A C10 C13 C4 179.6(7) . . . . ?
C15A C4 C13 C10 -164.0(7) . . . . ?
C15A C4 C13 C25 16.7(11) . . . . ?
C13 C4 C15A C6 177.8(7) . . . . ?
O1A C6 C15A C4 12.9(11) . . . . ?
O3 C6 C15A C4 -167.2(7) . . . . ?
C7 C5 C25 C13 -1.0(10) . . . . ?
N9 C5 C25 C13 179.3(6) . . . . ?
C10 C13 C25 C5 2.0(10) . . . . ?
C4 C13 C25 C5 -178.7(6) . . . . ?

_refine_diff_density_max         1.027
_refine_diff_density_min         -0.940
_refine_diff_density_rms         0.115

_shelxl_version_number           2013-2



