# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_C1
_database_code_depnum_ccdc_archive 'CCDC 1880806'
_audit_update_record             
;
2018-11-22 deposited with the CCDC.
2019-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H24 Cl2 N4 O2 Zn'
_chemical_formula_sum            'C15 H24 Cl2 N4 O2 Zn'
_chemical_formula_weight         428.65

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           orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   15.010(2)
_cell_length_b                   12.9027(19)
_cell_length_c                   20.065(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3886.0(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2973
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      23.02

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1776
_exptl_absorpt_coefficient_mu    1.554
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5226
_exptl_absorpt_correction_T_max  0.7164
_exptl_absorpt_process_details   'SADABS-2008/1 - Bruker AXS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         microsource

_diffrn_radiation_monochromator  'multilayer optics'

_diffrn_measurement_device_type  'Bruker APEX CCD'

_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            44769
_diffrn_reflns_av_R_equivalents  0.0983
_diffrn_reflns_av_sigmaI/netI    0.0477
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         26.43
_reflns_number_total             3991
_reflns_number_gt                3234
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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)+(0.0243P)²+5.2552P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3991
_refine_ls_number_parameters     224
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0877
_refine_ls_wR_factor_gt          0.0817
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
Zn1 Zn 0.030981(19) 0.16452(2) 0.315763(15) 0.01576(10) Uani 1 1 d . . .
O1 O -0.04503(12) 0.07445(14) 0.37994(9) 0.0193(4) Uani 1 1 d . . .
C1 C -0.09409(16) 0.32773(19) 0.28420(12) 0.0140(5) Uani 1 1 d . . .
N1 N -0.05074(13) 0.28212(17) 0.33466(10) 0.0137(4) Uani 1 1 d . . .
Cl1 Cl 0.02094(5) 0.10941(5) 0.21098(3) 0.02523(17) Uani 1 1 d . . .
Cl2 Cl 0.16647(4) 0.16844(6) 0.35947(4) 0.02619(17) Uani 1 1 d . . .
O2 O -0.12034(13) 0.04541(14) 0.47392(9) 0.0223(4) Uani 1 1 d . . .
C2 C -0.23951(17) 0.2616(2) 0.31725(14) 0.0216(6) Uani 1 1 d . . .
H2A H -0.2898 0.2435 0.2884 0.032 Uiso 1 1 calc R . .
H2B H -0.2619 0.2908 0.3591 0.032 Uiso 1 1 calc R . .
H2C H -0.2044 0.1993 0.3267 0.032 Uiso 1 1 calc R . .
N3 N -0.04865(14) 0.35867(16) 0.23026(11) 0.0147(5) Uani 1 1 d . . .
C3 C -0.22810(18) 0.4285(2) 0.25588(15) 0.0245(6) Uani 1 1 d . . .
H3A H -0.1833 0.4786 0.2410 0.037 Uiso 1 1 calc R . .
H3B H -0.2659 0.4604 0.2900 0.037 Uiso 1 1 calc R . .
H3C H -0.2649 0.4074 0.2179 0.037 Uiso 1 1 calc R . .
N4 N -0.13689(17) 0.52877(18) 0.50464(12) 0.0266(6) Uani 1 1 d . . .
C5 C -0.08626(19) 0.3527(2) 0.16320(13) 0.0228(6) Uani 1 1 d . . .
H5A H -0.0925 0.4227 0.1449 0.034 Uiso 1 1 calc R . .
H5B H -0.1449 0.3194 0.1652 0.034 Uiso 1 1 calc R . .
H5C H -0.0466 0.3119 0.1346 0.034 Uiso 1 1 calc R . .
C6 C -0.08169(16) 0.3010(2) 0.40014(12) 0.0138(5) Uani 1 1 d . . .
C7 C -0.09746(16) 0.2187(2) 0.44593(13) 0.0154(5) Uani 1 1 d . . .
C8 C -0.13117(17) 0.2451(2) 0.50946(13) 0.0186(6) Uani 1 1 d . . .
H8 H -0.1450 0.1909 0.5398 0.022 Uiso 1 1 calc R . .
C9 C -0.14477(18) 0.3456(2) 0.52904(13) 0.0200(6) Uani 1 1 d . . .
H9 H -0.1667 0.3599 0.5725 0.024 Uiso 1 1 calc R . .
C10 C -0.12617(17) 0.4285(2) 0.48454(13) 0.0179(6) Uani 1 1 d . . .
C11 C -0.09595(16) 0.4030(2) 0.41980(13) 0.0165(5) Uani 1 1 d . . .
H11 H -0.0851 0.4571 0.3888 0.020 Uiso 1 1 calc R . .
C12 C -0.08455(17) 0.1105(2) 0.42917(13) 0.0171(5) Uani 1 1 d . . .
C14 C -0.1194(2) 0.6141(2) 0.45946(16) 0.0331(7) Uani 1 1 d . . .
H14A H -0.0560 0.6146 0.4476 0.050 Uiso 1 1 calc R . .
H14B H -0.1349 0.6796 0.4812 0.050 Uiso 1 1 calc R . .
H14C H -0.1553 0.6057 0.4190 0.050 Uiso 1 1 calc R . .
C13 C -0.1088(2) -0.0639(2) 0.46206(15) 0.0272(7) Uani 1 1 d . . .
H13A H -0.1390 -0.0832 0.4205 0.041 Uiso 1 1 calc R . .
H13B H -0.1346 -0.1032 0.4992 0.041 Uiso 1 1 calc R . .
H13C H -0.0452 -0.0797 0.4584 0.041 Uiso 1 1 calc R . .
C15 C -0.1644(2) 0.5518(2) 0.57254(15) 0.0307(7) Uani 1 1 d . . .
H15A H -0.1656 0.6271 0.5791 0.046 Uiso 1 1 calc R . .
H15B H -0.1221 0.5206 0.6039 0.046 Uiso 1 1 calc R . .
H15C H -0.2240 0.5233 0.5804 0.046 Uiso 1 1 calc R . .
C4 C 0.04665(16) 0.3781(2) 0.23313(14) 0.0188(6) Uani 1 1 d . . .
H4A H 0.0787 0.3187 0.2145 0.028 Uiso 1 1 calc R . .
H4B H 0.0647 0.3884 0.2796 0.028 Uiso 1 1 calc R . .
H4C H 0.0608 0.4404 0.2072 0.028 Uiso 1 1 calc R . .
N2 N -0.18368(14) 0.33773(17) 0.28385(11) 0.0160(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
Zn1 N1 1.988(2) . ?
Zn1 O1 2.0761(18) . ?
Zn1 Cl2 2.2153(8) . ?
Zn1 Cl1 2.2246(8) . ?
O1 C12 1.243(3) . ?
C1 N1 1.340(3) . ?
C1 N3 1.340(3) . ?
C1 N2 1.351(3) . ?
N1 C6 1.414(3) . ?
O2 C12 1.342(3) . ?
O2 C13 1.441(3) . ?
C2 N2 1.454(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N3 C4 1.454(3) . ?
N3 C5 1.461(3) . ?
C3 N2 1.460(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
N4 C10 1.364(4) . ?
N4 C14 1.450(4) . ?
N4 C15 1.454(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C11 1.390(4) . ?
C6 C7 1.424(4) . ?
C7 C8 1.413(4) . ?
C7 C12 1.449(4) . ?
C8 C9 1.371(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.421(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.415(4) . ?
C11 H11 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?

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 O1 88.27(8) . . ?
N1 Zn1 Cl2 118.26(6) . . ?
O1 Zn1 Cl2 105.77(6) . . ?
N1 Zn1 Cl1 112.49(6) . . ?
O1 Zn1 Cl1 111.72(6) . . ?
Cl2 Zn1 Cl1 116.34(3) . . ?
C12 O1 Zn1 123.09(17) . . ?
N1 C1 N3 119.6(2) . . ?
N1 C1 N2 122.0(2) . . ?
N3 C1 N2 118.3(2) . . ?
C1 N1 C6 117.8(2) . . ?
C1 N1 Zn1 119.39(17) . . ?
C6 N1 Zn1 120.74(16) . . ?
C12 O2 C13 117.0(2) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 N3 C4 121.4(2) . . ?
C1 N3 C5 122.1(2) . . ?
C4 N3 C5 115.2(2) . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C10 N4 C14 120.9(2) . . ?
C10 N4 C15 120.3(2) . . ?
C14 N4 C15 118.8(2) . . ?
N3 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C6 N1 118.5(2) . . ?
C11 C6 C7 119.8(2) . . ?
N1 C6 C7 121.7(2) . . ?
C8 C7 C6 117.5(2) . . ?
C8 C7 C12 119.3(2) . . ?
C6 C7 C12 123.1(2) . . ?
C9 C8 C7 122.7(2) . . ?
C9 C8 H8 118.7 . . ?
C7 C8 H8 118.7 . . ?
C8 C9 C10 120.2(2) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
N4 C10 C11 122.0(2) . . ?
N4 C10 C9 120.3(2) . . ?
C11 C10 C9 117.6(2) . . ?
C6 C11 C10 122.1(2) . . ?
C6 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
O1 C12 O2 119.3(2) . . ?
O1 C12 C7 127.5(2) . . ?
O2 C12 C7 113.2(2) . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C1 N2 C2 120.5(2) . . ?
C1 N2 C3 122.2(2) . . ?
C2 N2 C3 117.1(2) . . ?

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
N1 Zn1 O1 C12 -31.3(2) . . . . ?
Cl2 Zn1 O1 C12 87.6(2) . . . . ?
Cl1 Zn1 O1 C12 -144.88(18) . . . . ?
N3 C1 N1 C6 145.7(2) . . . . ?
N2 C1 N1 C6 -38.7(3) . . . . ?
N3 C1 N1 Zn1 -50.4(3) . . . . ?
N2 C1 N1 Zn1 125.2(2) . . . . ?
O1 Zn1 N1 C1 -122.08(19) . . . . ?
Cl2 Zn1 N1 C1 130.91(17) . . . . ?
Cl1 Zn1 N1 C1 -9.2(2) . . . . ?
O1 Zn1 N1 C6 41.36(18) . . . . ?
Cl2 Zn1 N1 C6 -65.65(19) . . . . ?
Cl1 Zn1 N1 C6 154.20(16) . . . . ?
N1 C1 N3 C4 -21.8(4) . . . . ?
N2 C1 N3 C4 162.4(2) . . . . ?
N1 C1 N3 C5 144.3(2) . . . . ?
N2 C1 N3 C5 -31.5(4) . . . . ?
C1 N1 C6 C11 -50.1(3) . . . . ?
Zn1 N1 C6 C11 146.22(19) . . . . ?
C1 N1 C6 C7 130.5(3) . . . . ?
Zn1 N1 C6 C7 -33.1(3) . . . . ?
C11 C6 C7 C8 2.7(4) . . . . ?
N1 C6 C7 C8 -177.9(2) . . . . ?
C11 C6 C7 C12 179.7(2) . . . . ?
N1 C6 C7 C12 -0.9(4) . . . . ?
C6 C7 C8 C9 -3.2(4) . . . . ?
C12 C7 C8 C9 179.7(2) . . . . ?
C7 C8 C9 C10 1.0(4) . . . . ?
C14 N4 C10 C11 1.3(4) . . . . ?
C15 N4 C10 C11 -177.3(3) . . . . ?
C14 N4 C10 C9 -179.1(3) . . . . ?
C15 N4 C10 C9 2.2(4) . . . . ?
C8 C9 C10 N4 -177.9(3) . . . . ?
C8 C9 C10 C11 1.7(4) . . . . ?
N1 C6 C11 C10 -179.5(2) . . . . ?
C7 C6 C11 C10 -0.1(4) . . . . ?
N4 C10 C11 C6 177.4(2) . . . . ?
C9 C10 C11 C6 -2.1(4) . . . . ?
Zn1 O1 C12 O2 -169.48(17) . . . . ?
Zn1 O1 C12 C7 10.1(4) . . . . ?
C13 O2 C12 O1 1.1(4) . . . . ?
C13 O2 C12 C7 -178.6(2) . . . . ?
C8 C7 C12 O1 -169.5(3) . . . . ?
C6 C7 C12 O1 13.5(4) . . . . ?
C8 C7 C12 O2 10.1(3) . . . . ?
C6 C7 C12 O2 -166.9(2) . . . . ?
N1 C1 N2 C2 -30.1(4) . . . . ?
N3 C1 N2 C2 145.6(2) . . . . ?
N1 C1 N2 C3 144.3(3) . . . . ?
N3 C1 N2 C3 -40.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.43
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.078
####################################################################### 
# 
# 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_C2
_database_code_depnum_ccdc_archive 'CCDC 1880807'
_audit_update_record             
;
2018-11-22 deposited with the CCDC.
2019-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H18 Cl3 N3 O2 Zn'
_chemical_formula_sum            'C13 H18 Cl3 N3 O2 Zn'
_chemical_formula_weight         420.02

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(1)/n

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

_cell_length_a                   9.4998(4)
_cell_length_b                   16.0292(7)
_cell_length_c                   11.7929(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.0450(10)
_cell_angle_gamma                90.00
_cell_volume                     1734.20(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7357
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      30.18

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    1.886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6499
_exptl_absorpt_correction_T_max  0.7915
_exptl_absorpt_process_details   
'SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         microsource

_diffrn_radiation_monochromator  'multilayer optics'

_diffrn_measurement_device_type  'Bruker APEX CCD'

_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            26252
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         31.00
_reflns_number_total             5186
_reflns_number_gt                4561
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX'
_computing_cell_refinement       'Bruekr SAINT'
_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 and local progrmas'

_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)+(0.0317P)²+0.5069P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5186
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0667
_refine_ls_wR_factor_gt          0.0636
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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
Zn1 Zn 0.677578(18) 0.213815(10) 0.381067(14) 0.01441(5) Uani 1 1 d . . .
C1 C 0.64373(15) 0.33288(9) 0.18916(12) 0.0127(3) Uani 1 1 d . . .
O1 O 0.69147(12) 0.29351(7) 0.52190(9) 0.0181(2) Uani 1 1 d . . .
N1 N 0.58675(13) 0.30845(7) 0.27725(10) 0.0132(2) Uani 1 1 d . . .
Cl1 Cl 0.53949(4) 0.11231(2) 0.42006(3) 0.02072(8) Uani 1 1 d . . .
Cl2 Cl 0.89870(4) 0.18338(2) 0.36495(3) 0.02053(8) Uani 1 1 d . . .
C2 C 0.59757(18) 0.19512(9) 0.09822(14) 0.0202(3) Uani 1 1 d . . .
H2A H 0.5037 0.2009 0.1174 0.030 Uiso 1 1 calc R . .
H2B H 0.6559 0.1522 0.1483 0.030 Uiso 1 1 calc R . .
H2C H 0.5810 0.1790 0.0156 0.030 Uiso 1 1 calc R . .
O2 O 0.58677(11) 0.37691(7) 0.62620(9) 0.0169(2) Uani 1 1 d . . .
N2 N 0.67517(14) 0.27449(8) 0.11796(11) 0.0150(2) Uani 1 1 d . . .
Cl3 Cl 0.10279(4) 0.49673(3) 0.39218(4) 0.02466(9) Uani 1 1 d . . .
C4 C 0.68024(17) 0.44871(9) 0.06053(13) 0.0182(3) Uani 1 1 d . . .
H4A H 0.6285 0.4115 -0.0025 0.027 Uiso 1 1 calc R . .
H4B H 0.7817 0.4548 0.0571 0.027 Uiso 1 1 calc R . .
H4C H 0.6329 0.5035 0.0509 0.027 Uiso 1 1 calc R . .
C5 C 0.70612(17) 0.47247(10) 0.27206(13) 0.0193(3) Uani 1 1 d . . .
H5A H 0.7830 0.5112 0.2645 0.029 Uiso 1 1 calc R . .
H5B H 0.7379 0.4420 0.3464 0.029 Uiso 1 1 calc R . .
H5C H 0.6172 0.5039 0.2708 0.029 Uiso 1 1 calc R . .
C6 C 0.47873(15) 0.35711(9) 0.30653(12) 0.0128(3) Uani 1 1 d . . .
C7 C 0.36225(16) 0.38856(9) 0.21629(13) 0.0153(3) Uani 1 1 d . . .
H7 H 0.3630 0.3800 0.1367 0.018 Uiso 1 1 calc R . .
C8 C 0.24724(16) 0.43149(9) 0.24074(13) 0.0170(3) Uani 1 1 d . . .
H8 H 0.1696 0.4519 0.1789 0.020 Uiso 1 1 calc R . .
C9 C 0.24719(16) 0.44436(9) 0.35784(13) 0.0165(3) Uani 1 1 d . . .
C10 C 0.36000(16) 0.41623(9) 0.44820(13) 0.0154(3) Uani 1 1 d . . .
H10 H 0.3589 0.4267 0.5272 0.019 Uiso 1 1 calc R . .
C11 C 0.47659(15) 0.37216(9) 0.42424(12) 0.0129(3) Uani 1 1 d . . .
C12 C 0.59469(15) 0.34350(9) 0.52561(12) 0.0135(3) Uani 1 1 d . . .
C13 C 0.69397(17) 0.34750(11) 0.73086(13) 0.0216(3) Uani 1 1 d . . .
H13A H 0.6849 0.2869 0.7378 0.032 Uiso 1 1 calc R . .
H13B H 0.6768 0.3747 0.8005 0.032 Uiso 1 1 calc R . .
H13C H 0.7922 0.3611 0.7246 0.032 Uiso 1 1 calc R . .
C3 C 0.80579(19) 0.27901(10) 0.07455(15) 0.0229(3) Uani 1 1 d . . .
H3A H 0.7773 0.2820 -0.0114 0.034 Uiso 1 1 calc R . .
H3B H 0.8657 0.2292 0.0996 0.034 Uiso 1 1 calc R . .
H3C H 0.8619 0.3289 0.1064 0.034 Uiso 1 1 calc R . .
N3 N 0.67667(13) 0.41338(7) 0.17441(10) 0.0143(2) 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
Zn1 N1 1.9991(12) . ?
Zn1 O1 2.0721(11) . ?
Zn1 Cl1 2.2120(4) . ?
Zn1 Cl2 2.2123(4) . ?
C1 N2 1.3418(18) . ?
C1 N1 1.3481(18) . ?
C1 N3 1.3497(18) . ?
O1 C12 1.2289(17) . ?
N1 C6 1.4016(18) . ?
C2 N2 1.4584(19) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
O2 C12 1.3213(17) . ?
O2 C13 1.4594(18) . ?
N2 C3 1.4618(19) . ?
Cl3 C9 1.7433(15) . ?
C4 N3 1.4659(18) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 N3 1.4609(18) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.4141(19) . ?
C6 C11 1.4142(19) . ?
C7 C8 1.384(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.396(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.376(2) . ?
C10 C11 1.4029(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.4842(19) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?

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 O1 87.17(5) . . ?
N1 Zn1 Cl1 120.03(4) . . ?
O1 Zn1 Cl1 101.81(3) . . ?
N1 Zn1 Cl2 112.53(4) . . ?
O1 Zn1 Cl2 109.91(3) . . ?
Cl1 Zn1 Cl2 118.897(16) . . ?
N2 C1 N1 118.61(13) . . ?
N2 C1 N3 119.31(13) . . ?
N1 C1 N3 122.00(13) . . ?
C12 O1 Zn1 122.54(10) . . ?
C1 N1 C6 119.63(12) . . ?
C1 N1 Zn1 119.77(9) . . ?
C6 N1 Zn1 119.90(9) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C12 O2 C13 116.01(12) . . ?
C1 N2 C2 121.53(12) . . ?
C1 N2 C3 122.12(13) . . ?
C2 N2 C3 115.29(12) . . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N3 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 C7 119.52(12) . . ?
N1 C6 C11 122.33(12) . . ?
C7 C6 C11 118.04(13) . . ?
C8 C7 C6 121.76(13) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C9 118.86(13) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C10 C9 C8 121.15(13) . . ?
C10 C9 Cl3 118.65(11) . . ?
C8 C9 Cl3 120.21(11) . . ?
C9 C10 C11 120.38(13) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C6 119.79(13) . . ?
C10 C11 C12 117.70(12) . . ?
C6 C11 C12 122.50(12) . . ?
O1 C12 O2 120.92(13) . . ?
O1 C12 C11 126.10(13) . . ?
O2 C12 C11 112.98(12) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 N3 C5 121.44(12) . . ?
C1 N3 C4 123.28(12) . . ?
C5 N3 C4 115.24(12) . . ?

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
N1 Zn1 O1 C12 38.99(12) . . . . ?
Cl1 Zn1 O1 C12 -81.12(11) . . . . ?
Cl2 Zn1 O1 C12 151.96(10) . . . . ?
N2 C1 N1 C6 -142.04(13) . . . . ?
N3 C1 N1 C6 41.38(19) . . . . ?
N2 C1 N1 Zn1 47.53(16) . . . . ?
N3 C1 N1 Zn1 -129.05(12) . . . . ?
O1 Zn1 N1 C1 125.90(11) . . . . ?
Cl1 Zn1 N1 C1 -132.09(10) . . . . ?
Cl2 Zn1 N1 C1 15.50(12) . . . . ?
O1 Zn1 N1 C6 -44.50(11) . . . . ?
Cl1 Zn1 N1 C6 57.51(11) . . . . ?
Cl2 Zn1 N1 C6 -154.90(9) . . . . ?
N1 C1 N2 C2 26.8(2) . . . . ?
N3 C1 N2 C2 -156.56(13) . . . . ?
N1 C1 N2 C3 -140.87(14) . . . . ?
N3 C1 N2 C3 35.8(2) . . . . ?
C1 N1 C6 C7 45.00(19) . . . . ?
Zn1 N1 C6 C7 -144.59(11) . . . . ?
C1 N1 C6 C11 -138.89(14) . . . . ?
Zn1 N1 C6 C11 31.53(18) . . . . ?
N1 C6 C7 C8 175.03(14) . . . . ?
C11 C6 C7 C8 -1.3(2) . . . . ?
C6 C7 C8 C9 0.4(2) . . . . ?
C7 C8 C9 C10 1.0(2) . . . . ?
C7 C8 C9 Cl3 -178.99(12) . . . . ?
C8 C9 C10 C11 -1.4(2) . . . . ?
Cl3 C9 C10 C11 178.55(11) . . . . ?
C9 C10 C11 C6 0.5(2) . . . . ?
C9 C10 C11 C12 -179.95(13) . . . . ?
N1 C6 C11 C10 -175.36(13) . . . . ?
C7 C6 C11 C10 0.8(2) . . . . ?
N1 C6 C11 C12 5.1(2) . . . . ?
C7 C6 C11 C12 -178.74(13) . . . . ?
Zn1 O1 C12 O2 161.64(10) . . . . ?
Zn1 O1 C12 C11 -17.6(2) . . . . ?
C13 O2 C12 O1 -3.08(19) . . . . ?
C13 O2 C12 C11 176.22(12) . . . . ?
C10 C11 C12 O1 167.61(14) . . . . ?
C6 C11 C12 O1 -12.8(2) . . . . ?
C10 C11 C12 O2 -11.65(18) . . . . ?
C6 C11 C12 O2 167.90(13) . . . . ?
N2 C1 N3 C5 -152.85(13) . . . . ?
N1 C1 N3 C5 23.7(2) . . . . ?
N2 C1 N3 C4 29.5(2) . . . . ?
N1 C1 N3 C4 -153.91(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.939
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.076
####################################################################### 
# 
# 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_C3
_database_code_depnum_ccdc_archive 'CCDC 1880808'
_audit_update_record             
;
2018-11-22 deposited with the CCDC.
2019-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H21 Cl2 N3 O2 Zn'
_chemical_formula_sum            'C14 H21 Cl2 N3 O2 Zn'
_chemical_formula_weight         399.61

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(1)/n

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

_cell_length_a                   9.5828(4)
_cell_length_b                   16.0067(7)
_cell_length_c                   11.7969(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.9170(10)
_cell_angle_gamma                90.00
_cell_volume                     1748.53(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8247
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      30.38

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    1.719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6932
_exptl_absorpt_correction_T_max  0.7472
_exptl_absorpt_process_details   
'SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         microsource

_diffrn_radiation_monochromator  'multilayer optics'

_diffrn_measurement_device_type  'Bruker APEX CCD'

_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            26572
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         30.99
_reflns_number_total             5265
_reflns_number_gt                4671
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX'
_computing_cell_refinement       'Bruker SAINT'
_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)+(0.0375P)²+0.2927P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5265
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0261
_refine_ls_wR_factor_ref         0.0678
_refine_ls_wR_factor_gt          0.0658
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
Zn1 Zn 0.177750(16) 0.219838(9) 0.882559(12) 0.01452(5) Uani 1 1 d . . .
Cl1 Cl 0.03482(4) 0.11616(2) 0.90654(3) 0.02020(7) Uani 1 1 d . . .
O1 O 0.18056(11) 0.29949(6) 1.02068(8) 0.0191(2) Uani 1 1 d . . .
N1 N 0.17519(12) 0.41993(6) 0.67345(9) 0.0145(2) Uani 1 1 d . . .
C1 C 0.14878(13) 0.33857(8) 0.69056(10) 0.0132(2) Uani 1 1 d . . .
Cl2 Cl 0.40144(3) 0.18978(2) 0.87734(3) 0.02045(7) Uani 1 1 d . . .
O2 O 0.06939(10) 0.38347(6) 1.11881(8) 0.01728(19) Uani 1 1 d . . .
N2 N 0.18904(12) 0.28071(6) 0.62311(10) 0.0158(2) Uani 1 1 d . . .
C2 C 0.19104(15) 0.48083(8) 0.76812(12) 0.0195(3) Uani 1 1 d . . .
H2A H 0.2651 0.5218 0.7629 0.029 Uiso 1 1 calc R . .
H2B H 0.2199 0.4521 0.8439 0.029 Uiso 1 1 calc R . .
H2C H 0.0988 0.5095 0.7611 0.029 Uiso 1 1 calc R . .
N3 N 0.08978(11) 0.31327(7) 0.77650(9) 0.0137(2) Uani 1 1 d . . .
C3 C 0.18044(15) 0.45386(8) 0.55944(12) 0.0196(3) Uani 1 1 d . . .
H3A H 0.1350 0.4144 0.4974 0.029 Uiso 1 1 calc R . .
H3B H 0.2813 0.4627 0.5583 0.029 Uiso 1 1 calc R . .
H3C H 0.1286 0.5072 0.5462 0.029 Uiso 1 1 calc R . .
C4 C 0.32051(17) 0.28808(9) 0.58277(14) 0.0241(3) Uani 1 1 d . . .
H4A H 0.2948 0.2924 0.4970 0.036 Uiso 1 1 calc R . .
H4B H 0.3810 0.2386 0.6072 0.036 Uiso 1 1 calc R . .
H4C H 0.3738 0.3381 0.6171 0.036 Uiso 1 1 calc R . .
C5 C 0.11826(17) 0.19947(8) 0.60343(12) 0.0208(3) Uani 1 1 d . . .
H5A H 0.0248 0.2026 0.6227 0.031 Uiso 1 1 calc R . .
H5B H 0.1792 0.1576 0.6534 0.031 Uiso 1 1 calc R . .
H5C H 0.1032 0.1836 0.5209 0.031 Uiso 1 1 calc R . .
C6 C -0.02519(13) 0.35810(8) 0.80069(11) 0.0136(2) Uani 1 1 d . . .
C7 C -0.14010(14) 0.38533(8) 0.70756(11) 0.0159(2) Uani 1 1 d . . .
H7 H -0.1342 0.3775 0.6291 0.019 Uiso 1 1 calc R . .
C8 C -0.26124(15) 0.42322(9) 0.72776(12) 0.0191(3) Uani 1 1 d . . .
H8 H -0.3372 0.4404 0.6630 0.023 Uiso 1 1 calc R . .
C9 C -0.27380(14) 0.43664(9) 0.84234(12) 0.0191(3) Uani 1 1 d . . .
C13 C -0.15929(14) 0.41233(8) 0.93446(11) 0.0163(2) Uani 1 1 d . . .
H13 H -0.1646 0.4225 1.0126 0.020 Uiso 1 1 calc R . .
C14 C -0.03530(13) 0.37304(8) 0.91627(11) 0.0136(2) Uani 1 1 d . . .
C15 C -0.40872(17) 0.47439(11) 0.86376(14) 0.0300(3) Uani 1 1 d . . .
H15A H -0.4458 0.5175 0.8048 0.045 Uiso 1 1 calc R . .
H15B H -0.3863 0.4994 0.9422 0.045 Uiso 1 1 calc R . .
H15C H -0.4819 0.4307 0.8583 0.045 Uiso 1 1 calc R . .
C16 C 0.08064(13) 0.34817(8) 1.02006(11) 0.0138(2) Uani 1 1 d . . .
C17 C 0.17569(15) 0.35750(10) 1.22503(11) 0.0222(3) Uani 1 1 d . . .
H17A H 0.1671 0.2972 1.2364 0.033 Uiso 1 1 calc R . .
H17B H 0.1585 0.3875 1.2926 0.033 Uiso 1 1 calc R . .
H17C H 0.2729 0.3703 1.2176 0.033 Uiso 1 1 calc R . .


_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 N3 1.9924(10) . ?
Zn1 O1 2.0636(9) . ?
Zn1 Cl2 2.2132(4) . ?
Zn1 Cl1 2.2157(4) . ?
O1 C16 1.2331(16) . ?
N1 C1 1.3518(16) . ?
N1 C2 1.4605(16) . ?
N1 C3 1.4632(16) . ?
C1 N2 1.3408(15) . ?
C1 N3 1.3440(16) . ?
O2 C16 1.3238(15) . ?
O2 C17 1.4572(16) . ?
N2 C5 1.4572(17) . ?
N2 C4 1.4616(18) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N3 C6 1.4044(16) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.4094(17) . ?
C6 C14 1.4120(17) . ?
C7 C8 1.3837(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.4041(19) . ?
C8 H8 0.9500 . ?
C9 C13 1.3865(19) . ?
C9 C15 1.5063(18) . ?
C13 C14 1.4087(17) . ?
C13 H13 0.9500 . ?
C14 C16 1.4805(17) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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
N3 Zn1 O1 87.11(4) . . ?
N3 Zn1 Cl2 113.70(3) . . ?
O1 Zn1 Cl2 109.90(3) . . ?
N3 Zn1 Cl1 117.83(3) . . ?
O1 Zn1 Cl1 104.17(3) . . ?
Cl2 Zn1 Cl1 118.407(14) . . ?
C16 O1 Zn1 122.24(8) . . ?
C1 N1 C2 121.03(11) . . ?
C1 N1 C3 123.15(11) . . ?
C2 N1 C3 115.70(10) . . ?
N2 C1 N3 118.73(11) . . ?
N2 C1 N1 118.90(11) . . ?
N3 C1 N1 122.29(11) . . ?
C16 O2 C17 115.95(10) . . ?
C1 N2 C5 121.18(11) . . ?
C1 N2 C4 122.77(12) . . ?
C5 N2 C4 115.15(11) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 N3 C6 120.24(10) . . ?
C1 N3 Zn1 120.51(8) . . ?
C6 N3 Zn1 118.89(8) . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N3 C6 C7 119.73(11) . . ?
N3 C6 C14 122.36(11) . . ?
C7 C6 C14 117.79(11) . . ?
C8 C7 C6 121.54(12) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 121.09(12) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C13 C9 C8 117.70(12) . . ?
C13 C9 C15 121.43(12) . . ?
C8 C9 C15 120.86(12) . . ?
C9 C13 C14 122.30(12) . . ?
C9 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C13 C14 C6 119.53(11) . . ?
C13 C14 C16 118.49(11) . . ?
C6 C14 C16 121.98(11) . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 C16 O2 120.24(11) . . ?
O1 C16 C14 126.23(11) . . ?
O2 C16 C14 113.53(11) . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
N3 Zn1 O1 C16 39.33(10) . . . . ?
Cl2 Zn1 O1 C16 153.51(9) . . . . ?
Cl1 Zn1 O1 C16 -78.67(10) . . . . ?
C2 N1 C1 N2 -154.39(12) . . . . ?
C3 N1 C1 N2 29.70(18) . . . . ?
C2 N1 C1 N3 22.37(18) . . . . ?
C3 N1 C1 N3 -153.54(12) . . . . ?
N3 C1 N2 C5 27.35(18) . . . . ?
N1 C1 N2 C5 -155.77(12) . . . . ?
N3 C1 N2 C4 -141.23(13) . . . . ?
N1 C1 N2 C4 35.64(18) . . . . ?
N2 C1 N3 C6 -141.41(12) . . . . ?
N1 C1 N3 C6 41.83(18) . . . . ?
N2 C1 N3 Zn1 45.49(15) . . . . ?
N1 C1 N3 Zn1 -131.28(11) . . . . ?
O1 Zn1 N3 C1 126.56(10) . . . . ?
Cl2 Zn1 N3 C1 16.07(10) . . . . ?
Cl1 Zn1 N3 C1 -128.94(9) . . . . ?
O1 Zn1 N3 C6 -46.64(9) . . . . ?
Cl2 Zn1 N3 C6 -157.13(8) . . . . ?
Cl1 Zn1 N3 C6 57.86(10) . . . . ?
C1 N3 C6 C7 44.51(17) . . . . ?
Zn1 N3 C6 C7 -142.27(10) . . . . ?
C1 N3 C6 C14 -139.45(12) . . . . ?
Zn1 N3 C6 C14 33.77(16) . . . . ?
N3 C6 C7 C8 174.29(12) . . . . ?
C14 C6 C7 C8 -1.93(19) . . . . ?
C6 C7 C8 C9 0.5(2) . . . . ?
C7 C8 C9 C13 1.4(2) . . . . ?
C7 C8 C9 C15 -177.22(14) . . . . ?
C8 C9 C13 C14 -1.9(2) . . . . ?
C15 C9 C13 C14 176.69(13) . . . . ?
C9 C13 C14 C6 0.54(19) . . . . ?
C9 C13 C14 C16 -179.11(12) . . . . ?
N3 C6 C14 C13 -174.71(11) . . . . ?
C7 C6 C14 C13 1.40(18) . . . . ?
N3 C6 C14 C16 4.92(19) . . . . ?
C7 C6 C14 C16 -178.96(11) . . . . ?
Zn1 O1 C16 O2 163.98(8) . . . . ?
Zn1 O1 C16 C14 -15.72(18) . . . . ?
C17 O2 C16 O1 -3.23(17) . . . . ?
C17 O2 C16 C14 176.50(11) . . . . ?
C13 C14 C16 O1 164.57(13) . . . . ?
C6 C14 C16 O1 -15.1(2) . . . . ?
C13 C14 C16 O2 -15.14(16) . . . . ?
C6 C14 C16 O2 165.22(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.947
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.067
####################################################################### 
# 
# 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_C4
_database_code_depnum_ccdc_archive 'CCDC 1880809'
_audit_update_record             
;
2018-11-22 deposited with the CCDC.
2019-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            monoclinic
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H24 Cl2 N4 O2 Zn'
_chemical_formula_sum            'C15 H24 Cl2 N4 O2 Zn'
_chemical_formula_weight         428.65

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           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                   17.377(4)
_cell_length_b                   8.0888(16)
_cell_length_c                   13.258(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.439(4)
_cell_angle_gamma                90.00
_cell_volume                     1863.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1368
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      21.70

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    1.620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7816
_exptl_absorpt_correction_T_max  0.8950
_exptl_absorpt_process_details   'SADABS-2008/1 - Bruker AXS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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'

_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            22033
_diffrn_reflns_av_R_equivalents  0.0922
_diffrn_reflns_av_sigmaI/netI    0.0708
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.17
_diffrn_reflns_theta_max         26.50
_reflns_number_total             3855
_reflns_number_gt                2991
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0219P)²+2.8297P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3855
_refine_ls_number_parameters     224
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1039
_refine_ls_wR_factor_gt          0.0959
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
Zn1 Zn 0.19984(2) -0.29997(5) 0.57633(3) 0.01811(13) Uani 1 1 d . . .
O1 O 0.24715(14) -0.1268(3) 0.67618(17) 0.0207(5) Uani 1 1 d . . .
N1 N 0.20927(16) -0.1282(3) 0.4707(2) 0.0157(6) Uani 1 1 d . . .
C1 C 0.14869(18) -0.0658(4) 0.4192(2) 0.0158(7) Uani 1 1 d . . .
Cl2 Cl 0.29013(5) -0.49358(10) 0.58756(6) 0.0237(2) Uani 1 1 d . . .
O2 O 0.34436(13) 0.0348(3) 0.72331(16) 0.0185(5) Uani 1 1 d . . .
N2 N 0.09524(16) -0.1678(3) 0.3812(2) 0.0167(6) Uani 1 1 d . . .
C2 C 0.1114(2) -0.3390(4) 0.3548(3) 0.0228(8) Uani 1 1 d . . .
H2A H 0.0874 -0.3647 0.2895 0.034 Uiso 1 1 calc R . .
H2B H 0.0904 -0.4123 0.4066 0.034 Uiso 1 1 calc R . .
H2C H 0.1671 -0.3552 0.3504 0.034 Uiso 1 1 calc R . .
Cl3 Cl 0.07868(5) -0.35964(11) 0.61177(6) 0.0257(2) Uani 1 1 d . . .
C3 C 0.01422(19) -0.1212(5) 0.3719(3) 0.0232(8) Uani 1 1 d . . .
H3A H -0.0179 -0.2066 0.4029 0.035 Uiso 1 1 calc R . .
H3B H 0.0004 -0.1102 0.3004 0.035 Uiso 1 1 calc R . .
H3C H 0.0058 -0.0154 0.4062 0.035 Uiso 1 1 calc R . .
N3 N 0.13780(16) 0.0991(3) 0.4088(2) 0.0182(6) Uani 1 1 d . . .
C4 C 0.1657(2) 0.2162(4) 0.4839(3) 0.0229(8) Uani 1 1 d . . .
H4A H 0.1286 0.3068 0.4906 0.034 Uiso 1 1 calc R . .
H4B H 0.2155 0.2608 0.4628 0.034 Uiso 1 1 calc R . .
H4C H 0.1717 0.1600 0.5490 0.034 Uiso 1 1 calc R . .
N4 N 0.48216(17) 0.2483(4) 0.4301(2) 0.0213(6) Uani 1 1 d . . .
C5 C 0.1124(2) 0.1722(4) 0.3140(3) 0.0257(8) Uani 1 1 d . . .
H5A H 0.0658 0.2378 0.3253 0.039 Uiso 1 1 calc R . .
H5B H 0.1011 0.0842 0.2652 0.039 Uiso 1 1 calc R . .
H5C H 0.1530 0.2436 0.2876 0.039 Uiso 1 1 calc R . .
C6 C 0.27992(19) -0.0390(4) 0.4640(2) 0.0154(7) Uani 1 1 d . . .
C7 C 0.30747(19) 0.0046(4) 0.3687(2) 0.0175(7) Uani 1 1 d . . .
H7 H 0.2796 -0.0297 0.3104 0.021 Uiso 1 1 calc R . .
C8 C 0.37417(19) 0.0961(4) 0.3568(2) 0.0186(7) Uani 1 1 d . . .
H8 H 0.3906 0.1240 0.2908 0.022 Uiso 1 1 calc R . .
C9 C 0.41818(19) 0.1486(4) 0.4407(2) 0.0173(7) Uani 1 1 d . . .
C10 C 0.39251(19) 0.0988(4) 0.5357(2) 0.0178(7) Uani 1 1 d . . .
H10 H 0.4218 0.1287 0.5937 0.021 Uiso 1 1 calc R . .
C11 C 0.32501(19) 0.0060(4) 0.5483(2) 0.0158(7) Uani 1 1 d . . .
C12 C 0.30094(19) -0.0350(4) 0.6521(2) 0.0169(7) Uani 1 1 d . . .
C13 C 0.3264(2) -0.0090(4) 0.8271(2) 0.0216(8) Uani 1 1 d . . .
H13A H 0.3652 0.0388 0.8725 0.032 Uiso 1 1 calc R . .
H13B H 0.3265 -0.1296 0.8342 0.032 Uiso 1 1 calc R . .
H13C H 0.2755 0.0343 0.8444 0.032 Uiso 1 1 calc R . .
C14 C 0.52687(19) 0.2949(4) 0.5191(3) 0.0199(7) Uani 1 1 d . . .
H14A H 0.5701 0.3649 0.4989 0.030 Uiso 1 1 calc R . .
H14B H 0.5465 0.1951 0.5524 0.030 Uiso 1 1 calc R . .
H14C H 0.4940 0.3560 0.5659 0.030 Uiso 1 1 calc R . .
C15 C 0.5169(2) 0.2684(4) 0.3313(3) 0.0226(8) Uani 1 1 d . . .
H15A H 0.5653 0.3297 0.3383 0.034 Uiso 1 1 calc R . .
H15B H 0.4816 0.3295 0.2870 0.034 Uiso 1 1 calc R . .
H15C H 0.5272 0.1593 0.3022 0.034 Uiso 1 1 calc R . .


_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 1.981(3) . ?
Zn1 O1 2.091(2) . ?
Zn1 Cl3 2.2139(10) . ?
Zn1 Cl2 2.2210(10) . ?
O1 C12 1.237(4) . ?
N1 C1 1.348(4) . ?
N1 C6 1.427(4) . ?
C1 N2 1.338(4) . ?
C1 N3 1.354(4) . ?
O2 C12 1.330(4) . ?
O2 C13 1.457(4) . ?
N2 C2 1.456(4) . ?
N2 C3 1.462(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
N3 C5 1.455(4) . ?
N3 C4 1.455(4) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
N4 C9 1.382(4) . ?
N4 C15 1.456(4) . ?
N4 C14 1.457(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.400(5) . ?
C6 C11 1.408(4) . ?
C7 C8 1.385(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.410(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.399(5) . ?
C10 C11 1.403(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.479(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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 O1 86.76(10) . . ?
N1 Zn1 Cl3 112.77(8) . . ?
O1 Zn1 Cl3 112.43(7) . . ?
N1 Zn1 Cl2 118.68(8) . . ?
O1 Zn1 Cl2 98.96(7) . . ?
Cl3 Zn1 Cl2 120.30(4) . . ?
C12 O1 Zn1 122.2(2) . . ?
C1 N1 C6 116.6(3) . . ?
C1 N1 Zn1 123.5(2) . . ?
C6 N1 Zn1 118.3(2) . . ?
N2 C1 N1 119.8(3) . . ?
N2 C1 N3 118.3(3) . . ?
N1 C1 N3 121.9(3) . . ?
C12 O2 C13 116.3(3) . . ?
C1 N2 C2 122.9(3) . . ?
C1 N2 C3 122.6(3) . . ?
C2 N2 C3 114.3(3) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 N3 C5 121.9(3) . . ?
C1 N3 C4 121.8(3) . . ?
C5 N3 C4 115.1(3) . . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C9 N4 C15 119.7(3) . . ?
C9 N4 C14 119.6(3) . . ?
C15 N4 C14 118.5(3) . . ?
N3 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C11 117.3(3) . . ?
C7 C6 N1 118.9(3) . . ?
C11 C6 N1 123.8(3) . . ?
C8 C7 C6 121.9(3) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C7 C8 C9 121.4(3) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
N4 C9 C10 121.4(3) . . ?
N4 C9 C8 121.9(3) . . ?
C10 C9 C8 116.6(3) . . ?
C9 C10 C11 122.3(3) . . ?
C9 C10 H10 118.9 . . ?
C11 C10 H10 118.9 . . ?
C10 C11 C6 120.3(3) . . ?
C10 C11 C12 118.2(3) . . ?
C6 C11 C12 121.4(3) . . ?
O1 C12 O2 119.8(3) . . ?
O1 C12 C11 126.5(3) . . ?
O2 C12 C11 113.7(3) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N4 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
N1 Zn1 O1 C12 -40.8(3) . . . . ?
Cl3 Zn1 O1 C12 -154.1(2) . . . . ?
Cl2 Zn1 O1 C12 77.8(3) . . . . ?
O1 Zn1 N1 C1 -118.9(3) . . . . ?
Cl3 Zn1 N1 C1 -6.0(3) . . . . ?
Cl2 Zn1 N1 C1 142.6(2) . . . . ?
O1 Zn1 N1 C6 46.3(2) . . . . ?
Cl3 Zn1 N1 C6 159.3(2) . . . . ?
Cl2 Zn1 N1 C6 -52.1(2) . . . . ?
C6 N1 C1 N2 148.4(3) . . . . ?
Zn1 N1 C1 N2 -46.0(4) . . . . ?
C6 N1 C1 N3 -35.1(4) . . . . ?
Zn1 N1 C1 N3 130.4(3) . . . . ?
N1 C1 N2 C2 -26.1(5) . . . . ?
N3 C1 N2 C2 157.3(3) . . . . ?
N1 C1 N2 C3 147.9(3) . . . . ?
N3 C1 N2 C3 -28.7(5) . . . . ?
N2 C1 N3 C5 -44.8(5) . . . . ?
N1 C1 N3 C5 138.7(3) . . . . ?
N2 C1 N3 C4 148.2(3) . . . . ?
N1 C1 N3 C4 -28.3(5) . . . . ?
C1 N1 C6 C7 -50.6(4) . . . . ?
Zn1 N1 C6 C7 143.1(2) . . . . ?
C1 N1 C6 C11 130.6(3) . . . . ?
Zn1 N1 C6 C11 -35.7(4) . . . . ?
C11 C6 C7 C8 -3.4(5) . . . . ?
N1 C6 C7 C8 177.7(3) . . . . ?
C6 C7 C8 C9 0.7(5) . . . . ?
C15 N4 C9 C10 166.7(3) . . . . ?
C14 N4 C9 C10 3.8(5) . . . . ?
C15 N4 C9 C8 -15.2(5) . . . . ?
C14 N4 C9 C8 -178.2(3) . . . . ?
C7 C8 C9 N4 -176.0(3) . . . . ?
C7 C8 C9 C10 2.1(5) . . . . ?
N4 C9 C10 C11 176.0(3) . . . . ?
C8 C9 C10 C11 -2.2(5) . . . . ?
C9 C10 C11 C6 -0.6(5) . . . . ?
C9 C10 C11 C12 -177.6(3) . . . . ?
C7 C6 C11 C10 3.4(5) . . . . ?
N1 C6 C11 C10 -177.8(3) . . . . ?
C7 C6 C11 C12 -179.7(3) . . . . ?
N1 C6 C11 C12 -0.9(5) . . . . ?
Zn1 O1 C12 O2 -159.4(2) . . . . ?
Zn1 O1 C12 C11 19.3(5) . . . . ?
C13 O2 C12 O1 2.5(4) . . . . ?
C13 O2 C12 C11 -176.4(3) . . . . ?
C10 C11 C12 O1 -173.4(3) . . . . ?
C6 C11 C12 O1 9.7(5) . . . . ?
C10 C11 C12 O2 5.3(4) . . . . ?
C6 C11 C12 O2 -171.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.644
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.094
