# 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 2018

####################################################################### 
# 
# 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_A2
_database_code_depnum_ccdc_archive 'CCDC 1524154'
_audit_update_record             
;
2018-03-07 deposited with the CCDC.
2018-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H9 Cd N4 O4'
_chemical_formula_sum            'C17 H9 Cd N4 O4'
_chemical_formula_weight         445.68

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'
Cd Cd -0.8075 1.2024 '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                   12.5212(9)
_cell_length_b                   10.3722(6)
_cell_length_c                   13.4774(8)
_cell_angle_alpha                90
_cell_angle_beta                 111.045(7)
_cell_angle_gamma                90
_cell_volume                     1633.59(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2586
_cell_measurement_theta_min      3.2326
_cell_measurement_theta_max      29.3517

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.812
_exptl_crystal_F_000             876
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    1.369
_shelx_estimated_absorpt_T_min   0.744
_shelx_estimated_absorpt_T_max   0.762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8469
_exptl_absorpt_correction_T_max  0.8871
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6391
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.239
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3034
_reflns_number_gt                2593
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0316P)²+0.7887P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3034
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0716
_refine_ls_wR_factor_gt          0.0663
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
Cd1 Cd 0.43137(2) 0.27607(2) 0.17414(2) 0.02331(10) Uani 1 1 d . . . . .
N1 N 0.4516(2) 0.2616(2) 0.3484(2) 0.0225(6) Uani 1 1 d . . . . .
O1 O 0.5390(2) 0.0896(2) 0.24063(16) 0.0322(6) Uani 1 1 d . . . . .
N2 N 0.2436(2) 0.2008(3) 0.1115(2) 0.0284(6) Uani 1 1 d . . . . .
C3 C 0.5719(3) 0.0769(3) 0.3389(2) 0.0229(7) Uani 1 1 d . . . . .
C1 C 0.4159(3) 0.3142(3) 0.4233(2) 0.0215(7) Uani 1 1 d . . . . .
C2 C 0.5279(3) 0.1674(3) 0.4003(2) 0.0205(6) Uani 1 1 d . . . . .
N3 N 0.4656(2) 0.2597(2) 0.5193(2) 0.0225(6) Uani 1 1 d . . . . .
C5 C 0.5374(3) 0.1681(3) 0.5058(2) 0.0209(6) Uani 1 1 d . . . . .
C4 C 0.3354(3) 0.4231(3) 0.4036(2) 0.0242(7) Uani 1 1 d . . . . .
C6 C 0.3421(3) 0.5073(3) 0.4862(3) 0.0279(7) Uani 1 1 d . . . . .
H6A H 0.3976 0.4947 0.5532 0.034 Uiso 1 1 calc R U . . .
C15 C 0.1696(3) 0.2181(3) 0.0120(3) 0.0334(8) Uani 1 1 d . . . . .
H15A H 0.1837 0.2841 -0.0283 0.040 Uiso 1 1 calc R U . . .
C13 C 0.0501(3) 0.0439(3) 0.0243(2) 0.0277(7) Uani 1 1 d . . . . .
C14 C 0.0742(3) 0.1435(3) -0.0330(3) 0.0345(8) Uani 1 1 d . . . . .
H14A H 0.0255 0.1596 -0.1024 0.041 Uiso 1 1 calc R U . . .
C7 C 0.2668(3) 0.6093(3) 0.4692(3) 0.0358(9) Uani 1 1 d . . . . .
H7A H 0.2713 0.6652 0.5246 0.043 Uiso 1 1 calc R U . . .
C11 C 0.2179(3) 0.1085(4) 0.1679(3) 0.0363(9) Uani 1 1 d . . . . .
H11A H 0.2661 0.0968 0.2382 0.044 Uiso 1 1 calc R U . . .
C10 C 0.2517(3) 0.4439(4) 0.3041(3) 0.0374(9) Uani 1 1 d . . . . .
H10A H 0.2466 0.3883 0.2485 0.045 Uiso 1 1 calc R U . . .
C12 C 0.1241(3) 0.0298(4) 0.1278(3) 0.0371(9) Uani 1 1 d . . . . .
H12A H 0.1105 -0.0335 0.1707 0.045 Uiso 1 1 calc R U . . .
C8 C 0.1841(3) 0.6279(3) 0.3689(3) 0.0384(9) Uani 1 1 d . . . . .
C9 C 0.1764(3) 0.5449(4) 0.2865(3) 0.0430(10) Uani 1 1 d . . . . .
H9A H 0.1207 0.5574 0.2196 0.052 Uiso 1 1 calc R U . . .
C16 C 0.1053(4) 0.7348(4) 0.3501(4) 0.0556(12) Uani 1 1 d . . . . .
N4 N 0.0429(4) 0.8185(5) 0.3325(4) 0.0894(15) Uani 1 1 d . . . . .
O2 O 0.6377(2) -0.0143(2) 0.39084(17) 0.0278(5) Uani 1 1 d . . . . .
O3 O 0.6876(2) 0.0171(2) 0.58787(17) 0.0326(6) Uani 1 1 d . . . . .
H3 H 0.6758 0.0078 0.5244 0.049 Uiso 1 1 calc R U . . .
O4 O 0.60646(19) 0.1158(2) 0.68748(16) 0.0304(5) Uani 1 1 d . . . . .
C17 C 0.6130(3) 0.0976(3) 0.5997(2) 0.0245(7) Uani 1 1 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
Cd1 N1 2.275(2) . ?
Cd1 N3 2.306(2) 4_565 ?
Cd1 N2 2.329(3) . ?
Cd1 O1 2.343(2) . ?
Cd1 O2 2.387(2) 2_655 ?
Cd1 O4 2.411(2) 4_565 ?
N1 C1 1.357(4) . ?
N1 C2 1.370(4) . ?
O1 C3 1.245(3) . ?
N2 C11 1.331(4) . ?
N2 C15 1.340(4) . ?
C3 O2 1.284(4) . ?
C3 C2 1.482(4) . ?
C1 N3 1.343(4) . ?
C1 C4 1.474(4) . ?
C2 C5 1.384(4) . ?
N3 C5 1.365(4) . ?
N3 Cd1 2.306(2) 4_566 ?
C5 C17 1.474(4) . ?
C4 C10 1.390(5) . ?
C4 C6 1.394(4) . ?
C6 C7 1.380(5) . ?
C6 H6A 0.9300 . ?
C15 C14 1.368(5) . ?
C15 H15A 0.9300 . ?
C13 C12 1.377(5) . ?
C13 C14 1.387(5) . ?
C13 C13 1.497(6) 3 ?
C14 H14A 0.9300 . ?
C7 C8 1.391(5) . ?
C7 H7A 0.9300 . ?
C11 C12 1.372(5) . ?
C11 H11A 0.9300 . ?
C10 C9 1.371(5) . ?
C10 H10A 0.9300 . ?
C12 H12A 0.9300 . ?
C8 C9 1.381(5) . ?
C8 C16 1.445(5) . ?
C9 H9A 0.9300 . ?
C16 N4 1.134(6) . ?
O2 Cd1 2.387(2) 2_645 ?
O3 C17 1.305(4) . ?
O3 H3 0.8200 . ?
O4 C17 1.229(4) . ?
O4 Cd1 2.411(2) 4_566 ?

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 Cd1 N3 159.33(10) . 4_565 ?
N1 Cd1 N2 94.34(9) . . ?
N3 Cd1 N2 96.28(9) 4_565 . ?
N1 Cd1 O1 73.46(8) . . ?
N3 Cd1 O1 86.86(8) 4_565 . ?
N2 Cd1 O1 103.22(9) . . ?
N1 Cd1 O2 109.27(8) . 2_655 ?
N3 Cd1 O2 88.58(8) 4_565 2_655 ?
N2 Cd1 O2 89.25(9) . 2_655 ?
O1 Cd1 O2 167.11(8) . 2_655 ?
N1 Cd1 O4 101.11(8) . 4_565 ?
N3 Cd1 O4 71.51(8) 4_565 4_565 ?
N2 Cd1 O4 162.83(8) . 4_565 ?
O1 Cd1 O4 88.46(8) . 4_565 ?
O2 Cd1 O4 78.66(8) 2_655 4_565 ?
C1 N1 C2 105.2(2) . . ?
C1 N1 Cd1 142.9(2) . . ?
C2 N1 Cd1 111.87(18) . . ?
C3 O1 Cd1 114.8(2) . . ?
C11 N2 C15 116.5(3) . . ?
C11 N2 Cd1 116.9(2) . . ?
C15 N2 Cd1 124.3(2) . . ?
O1 C3 O2 124.1(3) . . ?
O1 C3 C2 118.6(3) . . ?
O2 C3 C2 117.2(3) . . ?
N3 C1 N1 112.7(3) . . ?
N3 C1 C4 123.2(3) . . ?
N1 C1 C4 124.1(3) . . ?
N1 C2 C5 107.9(3) . . ?
N1 C2 C3 119.9(3) . . ?
C5 C2 C3 131.7(3) . . ?
C1 N3 C5 105.3(2) . . ?
C1 N3 Cd1 140.1(2) . 4_566 ?
C5 N3 Cd1 110.76(19) . 4_566 ?
N3 C5 C2 108.9(3) . . ?
N3 C5 C17 118.8(3) . . ?
C2 C5 C17 132.2(3) . . ?
C10 C4 C6 118.8(3) . . ?
C10 C4 C1 121.5(3) . . ?
C6 C4 C1 119.7(3) . . ?
C7 C6 C4 120.4(3) . . ?
C7 C6 H6A 119.8 . . ?
C4 C6 H6A 119.8 . . ?
N2 C15 C14 123.2(3) . . ?
N2 C15 H15A 118.4 . . ?
C14 C15 H15A 118.4 . . ?
C12 C13 C14 116.2(3) . . ?
C12 C13 C13 122.2(4) . 3 ?
C14 C13 C13 121.7(4) . 3 ?
C15 C14 C13 120.2(3) . . ?
C15 C14 H14A 119.9 . . ?
C13 C14 H14A 119.9 . . ?
C6 C7 C8 119.6(3) . . ?
C6 C7 H7A 120.2 . . ?
C8 C7 H7A 120.2 . . ?
N2 C11 C12 123.4(3) . . ?
N2 C11 H11A 118.3 . . ?
C12 C11 H11A 118.3 . . ?
C9 C10 C4 121.2(3) . . ?
C9 C10 H10A 119.4 . . ?
C4 C10 H10A 119.4 . . ?
C11 C12 C13 120.4(3) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 C16 119.5(4) . . ?
C7 C8 C16 120.0(4) . . ?
C10 C9 C8 119.5(4) . . ?
C10 C9 H9A 120.3 . . ?
C8 C9 H9A 120.3 . . ?
N4 C16 C8 178.1(6) . . ?
C3 O2 Cd1 113.22(19) . 2_645 ?
C17 O3 H3 109.5 . . ?
C17 O4 Cd1 111.9(2) . 4_566 ?
O4 C17 O3 120.9(3) . . ?
O4 C17 C5 120.4(3) . . ?
O3 C17 C5 118.6(3) . . ?

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
Cd1 O1 C3 O2 -175.5(2) . . . . ?
Cd1 O1 C3 C2 8.3(3) . . . . ?
C2 N1 C1 N3 0.4(3) . . . . ?
Cd1 N1 C1 N3 -178.6(2) . . . . ?
C2 N1 C1 C4 177.9(3) . . . . ?
Cd1 N1 C1 C4 -1.1(5) . . . . ?
C1 N1 C2 C5 -1.2(3) . . . . ?
Cd1 N1 C2 C5 178.17(19) . . . . ?
C1 N1 C2 C3 171.3(3) . . . . ?
Cd1 N1 C2 C3 -9.3(3) . . . . ?
O1 C3 C2 N1 0.6(4) . . . . ?
O2 C3 C2 N1 -175.8(3) . . . . ?
O1 C3 C2 C5 171.1(3) . . . . ?
O2 C3 C2 C5 -5.4(5) . . . . ?
N1 C1 N3 C5 0.5(4) . . . . ?
C4 C1 N3 C5 -177.0(3) . . . . ?
N1 C1 N3 Cd1 -153.8(2) . . . 4_566 ?
C4 C1 N3 Cd1 28.7(5) . . . 4_566 ?
C1 N3 C5 C2 -1.2(3) . . . . ?
Cd1 N3 C5 C2 161.5(2) 4_566 . . . ?
C1 N3 C5 C17 174.8(3) . . . . ?
Cd1 N3 C5 C17 -22.5(3) 4_566 . . . ?
N1 C2 C5 N3 1.5(3) . . . . ?
C3 C2 C5 N3 -169.8(3) . . . . ?
N1 C2 C5 C17 -173.7(3) . . . . ?
C3 C2 C5 C17 14.9(6) . . . . ?
N3 C1 C4 C10 -153.1(3) . . . . ?
N1 C1 C4 C10 29.7(5) . . . . ?
N3 C1 C4 C6 26.5(5) . . . . ?
N1 C1 C4 C6 -150.7(3) . . . . ?
C10 C4 C6 C7 0.0(5) . . . . ?
C1 C4 C6 C7 -179.6(3) . . . . ?
C11 N2 C15 C14 -2.5(5) . . . . ?
Cd1 N2 C15 C14 159.7(3) . . . . ?
N2 C15 C14 C13 -0.1(6) . . . . ?
C12 C13 C14 C15 2.4(5) . . . . ?
C13 C13 C14 C15 -176.7(4) 3 . . . ?
C4 C6 C7 C8 -0.2(5) . . . . ?
C15 N2 C11 C12 2.7(5) . . . . ?
Cd1 N2 C11 C12 -160.8(3) . . . . ?
C6 C4 C10 C9 -0.1(5) . . . . ?
C1 C4 C10 C9 179.5(3) . . . . ?
N2 C11 C12 C13 -0.3(6) . . . . ?
C14 C13 C12 C11 -2.2(6) . . . . ?
C13 C13 C12 C11 176.9(4) 3 . . . ?
C6 C7 C8 C9 0.4(5) . . . . ?
C6 C7 C8 C16 -179.7(3) . . . . ?
C4 C10 C9 C8 0.3(6) . . . . ?
C7 C8 C9 C10 -0.4(6) . . . . ?
C16 C8 C9 C10 179.6(4) . . . . ?
O1 C3 O2 Cd1 -53.5(4) . . . 2_645 ?
C2 C3 O2 Cd1 122.8(2) . . . 2_645 ?
Cd1 O4 C17 O3 -165.0(2) 4_566 . . . ?
Cd1 O4 C17 C5 15.9(4) 4_566 . . . ?
N3 C5 C17 O4 4.2(4) . . . . ?
C2 C5 C17 O4 179.1(3) . . . . ?
N3 C5 C17 O3 -174.9(3) . . . . ?
C2 C5 C17 O3 0.0(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O2 0.82 1.70 2.521(3) 174.5 .

_refine_diff_density_max         0.586
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.092

####################################################################### 
# 
# 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 
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data_x
_database_code_depnum_ccdc_archive 'CCDC 1524204'
_audit_update_record             
;
2018-03-07 deposited with the CCDC.
2018-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H12 N5 O4 Zn'
_chemical_formula_sum            'C22 H12 N5 O4 Zn'
_chemical_formula_weight         475.74

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           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'

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

_cell_length_a                   11.4202(11)
_cell_length_b                   14.1684(15)
_cell_length_c                   13.0538(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2112.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2908
_cell_measurement_theta_min      3.2653
_cell_measurement_theta_max      29.3946

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_F_000             964
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.202
_shelx_estimated_absorpt_T_min   0.778
_shelx_estimated_absorpt_T_max   0.795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.57538
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7006
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.272
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1965
_reflns_number_gt                1834
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0591P)²+0.6632P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.41(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1965
_refine_ls_number_parameters     173
_refine_ls_number_restraints     192
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.1010
_refine_ls_wR_factor_gt          0.0957
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.114
_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 0.46989(5) 0.5000 0.5000 0.0248(3) Uani 1 2 d S T P . .
O1 O 0.4715(3) 0.3516(2) 0.5305(2) 0.0320(8) Uani 1 1 d . . . . .
O2 O 0.4882(4) 0.2480(2) 0.6572(3) 0.0506(11) Uani 1 1 d . . . . .
N1 N 0.6612(4) 0.5000 0.5000 0.0383(13) Uani 1 2 d S T P . .
N2 N 1.2808(4) 0.5000 0.5000 0.0344(12) Uani 1 2 d S T P . .
N3 N 0.4819(3) 0.5012(3) 0.6653(3) 0.0292(8) Uani 1 1 d . . . . .
C1 C 0.7213(5) 0.4278(4) 0.4632(5) 0.0469(17) Uani 1 1 d . . . . .
H1A H 0.6799 0.3767 0.4368 0.056 Uiso 1 1 calc R U . . .
C2 C 0.8422(5) 0.4241(4) 0.4619(5) 0.0426(16) Uani 1 1 d . . . . .
H2A H 0.8808 0.3716 0.4358 0.051 Uiso 1 1 calc R U . . .
C3 C 0.9050(5) 0.5000 0.5000 0.0314(13) Uani 1 2 d S T P . .
C4 C 1.0349(5) 0.5000 0.5000 0.0329(14) Uani 1 2 d S T P . .
C5 C 1.0984(4) 0.4165(3) 0.4982(7) 0.0427(12) Uani 1 1 d . . . . .
H5A H 1.0597 0.3588 0.4966 0.051 Uiso 1 1 calc R U . . .
C6 C 1.2192(4) 0.4195(3) 0.4989(7) 0.0439(12) Uani 1 1 d . . . . .
H6A H 1.2600 0.3627 0.4985 0.053 Uiso 1 1 calc R U . . .
C7 C 0.4820(4) 0.3331(3) 0.6234(4) 0.0308(11) Uani 1 1 d . . . . .
C8 C 0.4896(4) 0.4106(3) 0.6976(4) 0.0256(10) Uani 1 1 d . . . . .
C9 C 0.5000 0.5531(5) 0.7500 0.0366(18) Uani 1 2 d S T P . .
C10 C 0.5260(10) 0.6562(4) 0.7489(14) 0.051(4) Uani 0.5 1 d G U P A -1
C11 C 0.6306(9) 0.6946(5) 0.7841(11) 0.070(4) Uani 0.5 1 d G U P A -1
H11A H 0.6897 0.6552 0.8081 0.084 Uiso 0.5 1 calc R U P A -1
C12 C 0.6467(8) 0.7918(6) 0.7835(9) 0.085(4) Uani 0.5 1 d G U P A -1
H12A H 0.7167 0.8175 0.8070 0.103 Uiso 0.5 1 calc R U P A -1
C13 C 0.5584(10) 0.8506(4) 0.7476(9) 0.079(4) Uani 0.5 1 d G U P A -1
C14 C 0.4538(9) 0.8122(6) 0.7124(9) 0.083(4) Uani 0.5 1 d G U P A -1
H14A H 0.3947 0.8516 0.6884 0.100 Uiso 0.5 1 calc R U P A -1
C15 C 0.4377(8) 0.7150(6) 0.7131(11) 0.073(4) Uani 0.5 1 d G U P A -1
H15A H 0.3677 0.6893 0.6895 0.087 Uiso 0.5 1 calc R U P A -1
C16 C 0.573(2) 0.9514(10) 0.7446(18) 0.100(4) Uani 0.5 1 d . U P A -1
N4 N 0.592(2) 1.0304(9) 0.7420(19) 0.157(8) Uani 0.5 1 d . U P A -1


_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 O1 2.140(3) . ?
Zn1 O1 2.141(3) 4_566 ?
Zn1 N2 2.160(5) 1_455 ?
Zn1 N3 2.163(3) 4_566 ?
Zn1 N3 2.163(3) . ?
Zn1 N1 2.185(5) . ?
O1 C7 1.247(6) . ?
O2 C7 1.285(6) . ?
N1 C1 1.322(6) . ?
N1 C1 1.322(6) 4_566 ?
N2 C6 1.340(5) . ?
N2 C6 1.340(5) 4_566 ?
N2 Zn1 2.160(5) 1_655 ?
N3 C9 1.344(5) . ?
N3 C8 1.353(6) . ?
C1 C2 1.383(8) . ?
C1 H1A 0.9300 . ?
C2 C3 1.385(6) . ?
C2 H2A 0.9300 . ?
C3 C2 1.384(6) 4_566 ?
C3 C4 1.484(8) . ?
C4 C5 1.387(5) 4_566 ?
C4 C5 1.387(5) . ?
C5 C6 1.380(6) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.467(7) . ?
C8 C8 1.388(10) 3_656 ?
C9 N3 1.344(5) 3_656 ?
C9 C10 1.491(8) . ?
C10 C11 1.3900 . ?
C10 C15 1.3900 . ?
C11 C12 1.3900 . ?
C11 H11A 0.9300 . ?
C12 C13 1.3900 . ?
C12 H12A 0.9300 . ?
C13 C14 1.3900 . ?
C13 C16 1.439(14) . ?
C14 C15 1.3900 . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 N4 1.14(2) . ?

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
O1 Zn1 O1 179.00(17) . 4_566 ?
O1 Zn1 N2 90.50(9) . 1_455 ?
O1 Zn1 N2 90.50(9) 4_566 1_455 ?
O1 Zn1 N3 100.23(14) . 4_566 ?
O1 Zn1 N3 79.71(14) 4_566 4_566 ?
N2 Zn1 N3 93.64(9) 1_455 4_566 ?
O1 Zn1 N3 79.71(14) . . ?
O1 Zn1 N3 100.23(14) 4_566 . ?
N2 Zn1 N3 93.64(9) 1_455 . ?
N3 Zn1 N3 172.71(19) 4_566 . ?
O1 Zn1 N1 89.50(9) . . ?
O1 Zn1 N1 89.50(9) 4_566 . ?
N2 Zn1 N1 180.0 1_455 . ?
N3 Zn1 N1 86.36(9) 4_566 . ?
N3 Zn1 N1 86.36(9) . . ?
C7 O1 Zn1 112.8(3) . . ?
C1 N1 C1 117.5(6) . 4_566 ?
C1 N1 Zn1 121.2(3) . . ?
C1 N1 Zn1 121.2(3) 4_566 . ?
C6 N2 C6 116.7(5) . 4_566 ?
C6 N2 Zn1 121.7(3) . 1_655 ?
C6 N2 Zn1 121.7(3) 4_566 1_655 ?
C9 N3 C8 104.6(4) . . ?
C9 N3 Zn1 146.6(4) . . ?
C8 N3 Zn1 107.9(3) . . ?
N1 C1 C2 123.5(5) . . ?
N1 C1 H1A 118.3 . . ?
C2 C1 H1A 118.3 . . ?
C3 C2 C1 118.9(5) . . ?
C3 C2 H2A 120.5 . . ?
C1 C2 H2A 120.5 . . ?
C2 C3 C2 117.7(6) 4_566 . ?
C2 C3 C4 121.2(3) 4_566 . ?
C2 C3 C4 121.2(3) . . ?
C5 C4 C5 117.0(5) 4_566 . ?
C5 C4 C3 121.5(3) 4_566 . ?
C5 C4 C3 121.5(3) . . ?
C6 C5 C4 119.8(4) . . ?
C6 C5 H5A 120.1 . . ?
C4 C5 H5A 120.1 . . ?
N2 C6 C5 123.4(4) . . ?
N2 C6 H6A 118.3 . . ?
C5 C6 H6A 118.3 . . ?
O1 C7 O2 122.4(4) . . ?
O1 C7 C8 119.4(4) . . ?
O2 C7 C8 118.2(4) . . ?
N3 C8 C8 108.5(3) . 3_656 ?
N3 C8 C7 120.0(4) . . ?
C8 C8 C7 131.3(3) 3_656 . ?
N3 C9 N3 113.6(6) . 3_656 ?
N3 C9 C10 124.0(7) . . ?
N3 C9 C10 120.9(7) 3_656 . ?
C11 C10 C15 120.0 . . ?
C11 C10 C9 123.5(7) . . ?
C15 C10 C9 116.5(7) . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11A 120.0 . . ?
C10 C11 H11A 120.0 . . ?
C11 C12 C13 120.0 . . ?
C11 C12 H12A 120.0 . . ?
C13 C12 H12A 120.0 . . ?
C12 C13 C14 120.0 . . ?
C12 C13 C16 121.3(12) . . ?
C14 C13 C16 118.7(12) . . ?
C15 C14 C13 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C13 C14 H14A 120.0 . . ?
C14 C15 C10 120.0 . . ?
C14 C15 H15A 120.0 . . ?
C10 C15 H15A 120.0 . . ?
N4 C16 C13 176(3) . . ?

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
C1 N1 C1 C2 0.3(5) 4_566 . . . ?
Zn1 N1 C1 C2 -179.7(5) . . . . ?
N1 C1 C2 C3 -0.6(9) . . . . ?
C1 C2 C3 C2 0.3(4) . . . 4_566 ?
C1 C2 C3 C4 -179.7(4) . . . . ?
C2 C3 C4 C5 -23.7(5) 4_566 . . 4_566 ?
C2 C3 C4 C5 156.3(5) . . . 4_566 ?
C2 C3 C4 C5 156.3(5) 4_566 . . . ?
C2 C3 C4 C5 -23.7(5) . . . . ?
C5 C4 C5 C6 0.4(7) 4_566 . . . ?
C3 C4 C5 C6 -179.6(7) . . . . ?
C6 N2 C6 C5 0.4(7) 4_566 . . . ?
Zn1 N2 C6 C5 -179.6(7) 1_655 . . . ?
C4 C5 C6 N2 -0.8(15) . . . . ?
Zn1 O1 C7 O2 -177.9(4) . . . . ?
Zn1 O1 C7 C8 0.9(5) . . . . ?
C9 N3 C8 C8 1.1(6) . . . 3_656 ?
Zn1 N3 C8 C8 173.5(4) . . . 3_656 ?
C9 N3 C8 C7 -176.0(4) . . . . ?
Zn1 N3 C8 C7 -3.5(5) . . . . ?
O1 C7 C8 N3 1.9(7) . . . . ?
O2 C7 C8 N3 -179.1(5) . . . . ?
O1 C7 C8 C8 -174.3(6) . . . 3_656 ?
O2 C7 C8 C8 4.6(10) . . . 3_656 ?
C8 N3 C9 N3 -0.4(2) . . . 3_656 ?
Zn1 N3 C9 N3 -167.3(5) . . . 3_656 ?
C8 N3 C9 C10 165.8(6) . . . . ?
Zn1 N3 C9 C10 -1.1(8) . . . . ?
N3 C9 C10 C11 -116.6(8) . . . . ?
N3 C9 C10 C11 48.7(10) 3_656 . . . ?
N3 C9 C10 C15 65.3(9) . . . . ?
N3 C9 C10 C15 -129.4(6) 3_656 . . . ?
C15 C10 C11 C12 0.0 . . . . ?
C9 C10 C11 C12 -178.0(13) . . . . ?
C10 C11 C12 C13 0.0 . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C11 C12 C13 C16 -179.1(15) . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C16 C13 C14 C15 179.1(15) . . . . ?
C13 C14 C15 C10 0.0 . . . . ?
C11 C10 C15 C14 0.0 . . . . ?
C9 C10 C15 C14 178.2(13) . . . . ?

_refine_diff_density_max         0.553
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.062

