# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_aa
_database_code_depnum_ccdc_archive 'CCDC 1936360'
loop_
_audit_author_name
_audit_author_address
'pengfei hao'
;School of Chemical and Material Science, Shanxi Normal University
China
;
_audit_update_record             
;
2020-02-15 deposited with the CCDC.	2020-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H12 Cl2 N4 O5 Zn'
_chemical_formula_weight         572.65

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'
Cl Cl 0.1484 0.1585 '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                   7.2372(11)
_cell_length_b                   12.7860(19)
_cell_length_c                   14.237(2)
_cell_angle_alpha                68.774(3)
_cell_angle_beta                 78.572(4)
_cell_angle_gamma                81.970(4)
_cell_volume                     1200.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    4745
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      28.09

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    1.290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7446
_exptl_absorpt_correction_T_max  0.9759
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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            15663
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_sigmaI/netI    0.0910
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         28.33
_reflns_number_total             5968
_reflns_number_gt                3554
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0746P)²+2.4642P] 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         5968
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1390
_refine_ls_R_factor_gt           0.0700
_refine_ls_wR_factor_ref         0.1936
_refine_ls_wR_factor_gt          0.1670
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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
C1 C 1.1620(7) 0.7765(4) 0.2834(4) 0.0356(12) Uani 1 1 d . . .
C2 C 1.0369(7) 0.7114(4) 0.3774(4) 0.0314(11) Uani 1 1 d . . .
C3 C 1.0688(7) 0.7032(4) 0.4739(4) 0.0308(11) Uani 1 1 d . . .
C4 C 1.2205(7) 0.7547(4) 0.4848(4) 0.0352(12) Uani 1 1 d . . .
C5 C 1.3557(8) 0.8112(5) 0.3943(4) 0.0405(14) Uani 1 1 d . . .
C6 C 1.2404(8) 0.7521(5) 0.5790(4) 0.0416(14) Uani 1 1 d . . .
H6 H 1.3348 0.7908 0.5849 0.050 Uiso 1 1 calc R . .
C7 C 1.1229(8) 0.6931(5) 0.6655(4) 0.0391(13) Uani 1 1 d . . .
H7 H 1.1391 0.6920 0.7291 0.047 Uiso 1 1 calc R . .
C8 C 0.9819(7) 0.6358(4) 0.6584(4) 0.0307(11) Uani 1 1 d . . .
C9 C 0.9517(7) 0.6406(4) 0.5624(4) 0.0292(11) Uani 1 1 d . . .
C10 C 0.8028(7) 0.5856(4) 0.5528(4) 0.0313(11) Uani 1 1 d . . .
C11 C 0.7728(8) 0.5956(5) 0.4579(4) 0.0389(13) Uani 1 1 d . . .
H11 H 0.6754 0.5594 0.4516 0.047 Uiso 1 1 calc R . .
C12 C 0.8886(8) 0.6605(5) 0.3690(4) 0.0372(13) Uani 1 1 d . . .
H12 H 0.8644 0.6687 0.3048 0.045 Uiso 1 1 calc R . .
C13 C 0.8669(7) 0.5665(4) 0.7526(4) 0.0310(11) Uani 1 1 d . . .
C14 C 0.6823(7) 0.5172(4) 0.6459(4) 0.0323(12) Uani 1 1 d . . .
C15 C 0.3663(8) 0.3551(5) 1.0063(4) 0.0415(14) Uani 1 1 d . . .
H15 H 0.2872 0.3207 1.0669 0.050 Uiso 1 1 calc R . .
C16 C 0.2888(8) 0.4375(5) 0.9294(4) 0.0467(15) Uani 1 1 d . . .
H16 H 0.1596 0.4574 0.9371 0.056 Uiso 1 1 calc R . .
C17 C 0.4057(8) 0.4905(5) 0.8401(4) 0.0416(13) Uani 1 1 d . . .
H17 H 0.3574 0.5482 0.7870 0.050 Uiso 1 1 calc R . .
C18 C 0.5958(7) 0.4561(4) 0.8311(4) 0.0312(11) Uani 1 1 d . . .
C19 C 0.6632(7) 0.3712(4) 0.9109(4) 0.0320(12) Uani 1 1 d . . .
H19 H 0.7908 0.3470 0.9040 0.038 Uiso 1 1 calc R . .
C20 C 1.4633(8) 0.9901(4) 0.1944(4) 0.0374(13) Uani 1 1 d . . .
H20 H 1.3806 1.0255 0.2345 0.045 Uiso 1 1 calc R . .
C21 C 1.4473(7) 0.8791(4) 0.2122(4) 0.0356(12) Uani 1 1 d . . .
C22 C 1.5651(8) 0.8257(5) 0.1526(4) 0.0445(14) Uani 1 1 d . . .
H22 H 1.5571 0.7499 0.1645 0.053 Uiso 1 1 calc R . .
C23 C 1.6963(9) 0.8877(6) 0.0743(5) 0.0544(17) Uani 1 1 d . . .
H23 H 1.7764 0.8550 0.0312 0.065 Uiso 1 1 calc R . .
C24 C 1.7049(8) 0.9986(5) 0.0621(4) 0.0466(15) Uani 1 1 d . . .
H24 H 1.7930 1.0401 0.0096 0.056 Uiso 1 1 calc R . .
N1 N 0.5484(6) 0.3220(4) 0.9989(3) 0.0351(10) Uani 1 1 d . . .
N2 N 0.7226(6) 0.5121(3) 0.7395(3) 0.0307(10) Uani 1 1 d . . .
N3 N 1.3176(6) 0.8182(4) 0.2998(3) 0.0351(10) Uani 1 1 d . . .
N4 N 1.5938(6) 1.0498(4) 0.1214(3) 0.0371(11) Uani 1 1 d . . .
O1 O 1.1373(6) 0.7908(4) 0.1985(3) 0.0493(11) Uani 1 1 d . . .
O2 O 1.4966(6) 0.8484(4) 0.3999(3) 0.0621(13) Uani 1 1 d . . .
O3 O 0.8957(5) 0.5528(3) 0.8362(3) 0.0420(9) Uani 1 1 d . . .
O4 O 0.5591(6) 0.4652(3) 0.6422(3) 0.0485(11) Uani 1 1 d . . .
O5 O 0.0553(13) 0.0170(8) 0.3458(8) 0.077(3) Uani 0.50 1 d P . .
O6 O 0.7609(15) 0.9406(9) 0.4970(8) 0.083(3) Uani 0.50 1 d P . .
Zn1 Zn 0.64446(9) 0.20312(5) 1.12186(5) 0.0380(2) Uani 1 1 d . . .
Cl1 Cl 0.4623(2) 0.22479(13) 1.25984(10) 0.0460(4) Uani 1 1 d . . .
Cl2 Cl 0.9531(2) 0.21018(17) 1.10295(14) 0.0641(5) 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
C1 O1 1.202(6) . ?
C1 N3 1.402(6) . ?
C1 C2 1.492(6) . ?
C2 C12 1.376(7) . ?
C2 C3 1.402(7) . ?
C3 C9 1.408(6) . ?
C3 C4 1.417(6) . ?
C4 C6 1.365(7) . ?
C4 C5 1.471(7) . ?
C5 O2 1.212(6) . ?
C5 N3 1.396(7) . ?
C6 C7 1.378(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.376(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.405(7) . ?
C8 C13 1.476(6) . ?
C9 C10 1.420(6) . ?
C10 C11 1.368(7) . ?
C10 C14 1.482(6) . ?
C11 C12 1.416(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 O3 1.194(6) . ?
C13 N2 1.408(6) . ?
C14 O4 1.203(6) . ?
C14 N2 1.397(6) . ?
C15 N1 1.322(7) . ?
C15 C16 1.367(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.379(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.381(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.373(7) . ?
C18 N2 1.445(6) . ?
C19 N1 1.349(6) . ?
C19 H19 0.9300 . ?
C20 N4 1.339(6) . ?
C20 C21 1.366(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.371(8) . ?
C21 N3 1.442(6) . ?
C22 C23 1.387(8) . ?
C22 H22 0.9300 . ?
C23 C24 1.373(8) . ?
C23 H23 0.9300 . ?
C24 N4 1.332(7) . ?
C24 H24 0.9300 . ?
N1 Zn1 2.029(4) . ?
N4 Zn1 2.047(4) 1_664 ?
Zn1 N4 2.047(4) 1_446 ?
Zn1 Cl2 2.2071(17) . ?
Zn1 Cl1 2.2226(15) . ?

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 C1 N3 120.9(4) . . ?
O1 C1 C2 123.5(5) . . ?
N3 C1 C2 115.6(4) . . ?
C12 C2 C3 120.1(4) . . ?
C12 C2 C1 119.7(4) . . ?
C3 C2 C1 120.2(4) . . ?
C2 C3 C9 120.0(4) . . ?
C2 C3 C4 121.3(4) . . ?
C9 C3 C4 118.7(4) . . ?
C6 C4 C3 120.0(4) . . ?
C6 C4 C5 120.3(4) . . ?
C3 C4 C5 119.7(5) . . ?
O2 C5 N3 120.5(5) . . ?
O2 C5 C4 122.6(5) . . ?
N3 C5 C4 116.9(4) . . ?
C4 C6 C7 121.0(5) . . ?
C4 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 120.4(5) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 120.2(4) . . ?
C7 C8 C13 119.4(4) . . ?
C9 C8 C13 120.4(4) . . ?
C8 C9 C3 119.4(4) . . ?
C8 C9 C10 121.2(4) . . ?
C3 C9 C10 119.4(4) . . ?
C11 C10 C9 119.7(4) . . ?
C11 C10 C14 120.8(4) . . ?
C9 C10 C14 119.5(4) . . ?
C10 C11 C12 120.7(4) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C2 C12 C11 120.1(5) . . ?
C2 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
O3 C13 N2 120.5(4) . . ?
O3 C13 C8 123.2(4) . . ?
N2 C13 C8 116.3(4) . . ?
O4 C14 N2 120.9(4) . . ?
O4 C14 C10 122.2(5) . . ?
N2 C14 C10 116.9(4) . . ?
N1 C15 C16 123.2(5) . . ?
N1 C15 H15 118.4 . . ?
C16 C15 H15 118.4 . . ?
C15 C16 C17 118.8(5) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C16 C17 C18 118.5(5) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
C19 C18 C17 119.5(5) . . ?
C19 C18 N2 120.8(5) . . ?
C17 C18 N2 119.8(5) . . ?
N1 C19 C18 121.5(5) . . ?
N1 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
N4 C20 C21 122.4(5) . . ?
N4 C20 H20 118.8 . . ?
C21 C20 H20 118.8 . . ?
C20 C21 C22 119.9(5) . . ?
C20 C21 N3 118.5(5) . . ?
C22 C21 N3 121.3(5) . . ?
C21 C22 C23 118.3(5) . . ?
C21 C22 H22 120.9 . . ?
C23 C22 H22 120.9 . . ?
C24 C23 C22 118.3(5) . . ?
C24 C23 H23 120.8 . . ?
C22 C23 H23 120.8 . . ?
N4 C24 C23 123.4(5) . . ?
N4 C24 H24 118.3 . . ?
C23 C24 H24 118.3 . . ?
C15 N1 C19 118.5(5) . . ?
C15 N1 Zn1 118.6(3) . . ?
C19 N1 Zn1 122.8(4) . . ?
C14 N2 C13 125.6(4) . . ?
C14 N2 C18 118.2(4) . . ?
C13 N2 C18 115.9(4) . . ?
C5 N3 C1 125.9(4) . . ?
C5 N3 C21 115.6(4) . . ?
C1 N3 C21 118.5(4) . . ?
C24 N4 C20 117.6(5) . . ?
C24 N4 Zn1 122.6(3) . 1_664 ?
C20 N4 Zn1 118.9(4) . 1_664 ?
N1 Zn1 N4 107.27(18) . 1_446 ?
N1 Zn1 Cl2 108.52(13) . . ?
N4 Zn1 Cl2 108.10(14) 1_446 . ?
N1 Zn1 Cl1 106.96(13) . . ?
N4 Zn1 Cl1 106.10(12) 1_446 . ?
Cl2 Zn1 Cl1 119.32(6) . . ?

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
C15 H15 O3 0.93 2.56 3.100(7) 117.2 2_667
C15 H15 Cl2 0.93 2.84 3.513(5) 130.6 1_455
C16 H16 O3 0.93 2.52 3.307(7) 142.1 1_455
C19 H19 O1 0.93 2.61 3.067(7) 110.9 2_766
C20 H20 O5 0.93 2.56 3.349(10) 143.4 1_665
C20 H20 Cl1 0.93 2.85 3.448(5) 122.8 1_664
C23 H23 Cl2 0.93 2.72 3.638(6) 170.2 2_866

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.811
_refine_diff_density_min         -0.784
_refine_diff_density_rms         0.118
####################################################################### 
# 
# 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_aa_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1936362'
loop_
_audit_author_name
_audit_author_address
'Pengfei Hao'
;School of Chemical and Material Science, Shanxi Normal University
China
;
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2020-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H21 Cl2 N5 O5 Zn'
_chemical_formula_weight         643.77

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'
Cl Cl 0.1484 0.1585 '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/c  '

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

_cell_length_a                   7.5740(8)
_cell_length_b                   12.2366(12)
_cell_length_c                   15.0059(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.741(3)
_cell_angle_gamma                90.00
_cell_volume                     1387.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9904
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      28.26

_exptl_crystal_description       rodlike
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    1.126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5050
_exptl_absorpt_correction_T_max  0.8909
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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            21547
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0155
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.33
_diffrn_reflns_theta_max         28.37
_reflns_number_total             3446
_reflns_number_gt                2949
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0429P)²+0.5129P] 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         3446
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0879
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.002
_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 0.5000 1.150254(19) 0.7500 0.04498(11) Uani 1 2 d S . .
Cl1 Cl 0.38507(9) 1.23470(5) 0.62988(4) 0.06971(18) Uani 1 1 d . . .
C1 C 0.3076(3) 1.03150(15) 0.88828(14) 0.0606(6) Uani 1 1 d . . .
H1 H 0.3354 1.0927 0.9231 0.073 Uiso 1 1 calc R . .
C2 C 0.2424(3) 0.94038(15) 0.92878(13) 0.0595(5) Uani 1 1 d . . .
H2 H 0.2253 0.9402 0.9896 0.071 Uiso 1 1 calc R . .
C3 C 0.2035(2) 0.85020(12) 0.87741(12) 0.0420(4) Uani 1 1 d . . .
C4 C 0.2202(3) 0.85430(14) 0.78678(12) 0.0497(4) Uani 1 1 d . . .
H4 H 0.1896 0.7947 0.7505 0.060 Uiso 1 1 calc R . .
C5 C 0.2836(3) 0.94918(15) 0.75127(12) 0.0529(5) Uani 1 1 d . . .
H5 H 0.2927 0.9531 0.6898 0.063 Uiso 1 1 calc R . .
C6 C -0.0230(2) 0.74846(13) 0.94899(11) 0.0394(3) Uani 1 1 d . . .
C7 C -0.0809(2) 0.64292(12) 0.98522(10) 0.0350(3) Uani 1 1 d . . .
C8 C 0.02993(19) 0.55048(11) 0.98378(9) 0.0322(3) Uani 1 1 d . . .
C9 C 0.1990(2) 0.55608(12) 0.94989(10) 0.0348(3) Uani 1 1 d . . .
C10 C 0.2628(2) 0.66093(13) 0.91490(11) 0.0384(3) Uani 1 1 d . . .
C11 C -0.2453(2) 0.63538(13) 1.01868(11) 0.0399(3) Uani 1 1 d . . .
H11 H -0.3179 0.6966 1.0193 0.048 Uiso 1 1 calc R . .
C12 C -0.3034(2) 0.53552(13) 1.05183(11) 0.0394(3) Uani 1 1 d . . .
H12 H -0.4138 0.5312 1.0753 0.047 Uiso 1 1 calc R . .
C13 C 0.0000 0.6623(2) 0.2500 0.0688(9) Uani 1 2 d S . .
H13A H -0.0862 0.7064 0.2774 0.103 Uiso 0.50 1 calc PR . .
H13B H 0.0044 0.6826 0.1884 0.103 Uiso 0.50 1 calc PR . .
H13C H 0.1141 0.6735 0.2803 0.103 Uiso 0.50 1 calc PR . .
C14 C 0.2353(3) 0.5067(2) 0.21393(17) 0.0631(6) Uani 1 1 d . . .
H14A H 0.240(4) 0.544(2) 0.156(2) 0.089(8) Uiso 1 1 d . . .
H14B H 0.307(4) 0.539(2) 0.257(2) 0.090(9) Uiso 1 1 d . . .
H14C H 0.283(6) 0.433(4) 0.210(3) 0.153(16) Uiso 1 1 d . . .
C15 C 0.0631(5) 0.4664(3) 0.2384(2) 0.0426(7) Uani 0.50 1 d P . .
N1 N 0.3327(2) 1.03577(11) 0.80086(11) 0.0499(4) Uani 1 1 d . . .
N2 N 0.14663(19) 0.74999(10) 0.91712(9) 0.0391(3) Uani 1 1 d . . .
N3 N 0.0495(4) 0.5461(2) 0.2440(3) 0.0485(8) Uani 0.50 1 d P . .
O1 O -0.11449(19) 0.82963(10) 0.94525(11) 0.0575(4) Uani 1 1 d . . .
O2 O 0.40684(17) 0.67133(11) 0.88577(10) 0.0531(3) Uani 1 1 d . . .
O3 O 0.0000 0.36971(16) 0.2500 0.0684(6) Uani 1 2 d S . .


_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 2.0680(14) 2_656 ?
Zn1 N1 2.0680(15) . ?
Zn1 Cl1 2.2068(6) 2_656 ?
Zn1 Cl1 2.2068(6) . ?
C1 N1 1.339(2) . ?
C1 C2 1.377(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.367(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(3) . ?
C3 N2 1.4413(19) . ?
C4 C5 1.377(2) . ?
C4 H4 0.9300 . ?
C5 N1 1.334(2) . ?
C5 H5 0.9300 . ?
C6 O1 1.210(2) . ?
C6 N2 1.400(2) . ?
C6 C7 1.479(2) . ?
C7 C11 1.376(2) . ?
C7 C8 1.410(2) . ?
C8 C9 1.410(2) . ?
C8 C8 1.413(3) 3_567 ?
C9 C12 1.373(2) 3_567 ?
C9 C10 1.479(2) . ?
C10 O2 1.208(2) . ?
C10 N2 1.402(2) . ?
C11 C12 1.401(2) . ?
C11 H11 0.9300 . ?
C12 C9 1.373(2) 3_567 ?
C12 H12 0.9300 . ?
C13 N3 1.474(4) 2 ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.463(4) . ?
C14 N3 1.581(4) . ?
C14 H14A 0.98(3) . ?
C14 H14B 0.91(3) . ?
C14 H14C 0.98(4) . ?
C15 N3 0.985(4) . ?
C15 C15 1.039(7) 2 ?
C15 O3 1.292(4) . ?
C15 N3 1.333(4) 2 ?
N3 N3 0.782(6) 2 ?
N3 C15 1.333(4) 2 ?
O3 C15 1.292(4) 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
N1 Zn1 N1 94.72(9) 2_656 . ?
N1 Zn1 Cl1 113.59(5) 2_656 2_656 ?
N1 Zn1 Cl1 103.55(5) . 2_656 ?
N1 Zn1 Cl1 103.55(5) 2_656 . ?
N1 Zn1 Cl1 113.59(5) . . ?
Cl1 Zn1 Cl1 124.16(4) 2_656 . ?
N1 C1 C2 122.83(17) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C3 C2 C1 118.37(17) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 119.85(15) . . ?
C2 C3 N2 120.85(16) . . ?
C4 C3 N2 119.29(14) . . ?
C3 C4 C5 118.07(16) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
N1 C5 C4 123.06(17) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
O1 C6 N2 120.58(15) . . ?
O1 C6 C7 123.44(16) . . ?
N2 C6 C7 115.97(14) . . ?
C11 C7 C8 120.38(13) . . ?
C11 C7 C6 119.33(14) . . ?
C8 C7 C6 120.28(14) . . ?
C7 C8 C9 121.48(13) . . ?
C7 C8 C8 119.44(17) . 3_567 ?
C9 C8 C8 119.08(17) . 3_567 ?
C12 C9 C8 120.30(14) 3_567 . ?
C12 C9 C10 120.00(14) 3_567 . ?
C8 C9 C10 119.70(14) . . ?
O2 C10 N2 120.63(14) . . ?
O2 C10 C9 122.90(16) . . ?
N2 C10 C9 116.47(14) . . ?
C7 C11 C12 120.05(15) . . ?
C7 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C9 C12 C11 120.74(15) 3_567 . ?
C9 C12 H12 119.6 3_567 . ?
C11 C12 H12 119.6 . . ?
N3 C13 H13A 109.5 2 . ?
N3 C13 H13B 109.5 2 . ?
H13A C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 2 . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 N3 37.51(17) . . ?
C15 C14 H14A 117.6(16) . . ?
N3 C14 H14A 101.4(17) . . ?
C15 C14 H14B 117.8(18) . . ?
N3 C14 H14B 99.5(18) . . ?
H14A C14 H14B 112(2) . . ?
C15 C14 H14C 92(3) . . ?
N3 C14 H14C 130(3) . . ?
H14A C14 H14C 110(3) . . ?
H14B C14 H14C 104(3) . . ?
N3 C15 C15 82.4(3) . 2 ?
N3 C15 O3 148.6(4) . . ?
C15 C15 O3 66.30(16) 2 . ?
N3 C15 N3 35.6(3) . 2 ?
C15 C15 N3 47.08(18) 2 2 ?
O3 C15 N3 113.3(3) . 2 ?
N3 C15 C14 77.8(3) . . ?
C15 C15 C14 159.9(2) 2 . ?
O3 C15 C14 133.3(3) . . ?
N3 C15 C14 113.3(3) 2 . ?
C5 N1 C1 117.61(15) . . ?
C5 N1 Zn1 119.17(12) . . ?
C1 N1 Zn1 121.18(13) . . ?
C6 N2 C10 126.08(13) . . ?
C6 N2 C3 117.27(14) . . ?
C10 N2 C3 116.52(14) . . ?
N3 N3 C15 97.3(3) 2 . ?
N3 N3 C15 47.12(19) 2 2 ?
C15 N3 C15 50.6(4) . 2 ?
N3 N3 C14 161.8(2) 2 . ?
C15 N3 C14 64.7(3) . . ?
C15 N3 C14 115.2(3) 2 . ?
C15 O3 C15 47.4(3) . 2 ?

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
C4 H4 O3 0.93 2.47 3.237(2) 139.7 3_566
C1 H1 Cl1 0.93 2.89 3.429(2) 118.2 2_656

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        28.37
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.043
_chemical_properties_physical    Light-sensitive,Photo-sensitive
