# 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 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1050186'
_audit_update_record             
;
2015-02-18 deposited with the CCDC.
2015-12-16 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         ?
_chemical_formula_sum            'C12 H16 Cl4 N2 O3 Zn2'
_chemical_formula_weight         508.81

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'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.4731(5)
_cell_length_b                   13.5296(8)
_cell_length_c                   29.0220(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3719.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4084
_cell_measurement_theta_min      2.9706
_cell_measurement_theta_max      32.2080

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.817
_exptl_crystal_F_000             2032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    3.165
_shelx_estimated_absorpt_T_min   0.421
_shelx_estimated_absorpt_T_max   0.600
_exptl_absorpt_correction_T_min  0.48627
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_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.
;



_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18005
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.977
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3272
_reflns_number_gt                2669
_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       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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     
'w=1/[σ²(Fo²)+(0.0216P)²+2.5991P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3272
_refine_ls_number_parameters     224
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.0865
_refine_ls_wR_factor_gt          0.0804
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.150
_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_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 0.45062(6) 0.44027(4) 0.64212(2) 0.01866(15) Uani 1 1 d . . . . .
Zn2 Zn 0.05876(6) 0.56131(4) 0.60905(2) 0.01962(15) Uani 1 1 d . . . . .
Cl1 Cl 0.25385(12) 0.55844(9) 0.65783(3) 0.0199(3) Uani 1 1 d . . . . .
Cl2 Cl -0.12051(13) 0.62171(9) 0.65370(4) 0.0273(3) Uani 1 1 d . . . . .
Cl3 Cl 0.01856(14) 0.40620(10) 0.58531(5) 0.0320(3) Uani 1 1 d . . . . .
Cl4 Cl 0.10362(14) 0.66469(9) 0.55055(4) 0.0273(3) Uani 1 1 d . . . . .
O1 O 0.6192(4) 0.3426(3) 0.61969(11) 0.0256(8) Uani 1 1 d D . . . .
O2 O 0.5905(3) 0.5271(3) 0.68516(10) 0.0224(8) Uani 1 1 d D . . . .
O3 O 0.3137(4) 0.3422(3) 0.61091(11) 0.0270(8) Uani 1 1 d D . . . .
N1 N 0.5345(4) 0.5140(3) 0.58598(12) 0.0170(9) Uani 1 1 d . . . . .
N2 N 0.4336(4) 0.3741(3) 0.70656(12) 0.0155(9) Uani 1 1 d . . . . .
C1 C 0.5073(5) 0.6087(4) 0.57526(15) 0.0220(11) Uani 1 1 d . . . . .
H1 H 0.4379 0.6431 0.5926 0.026 Uiso 1 1 calc R U . . .
C2 C 0.5747(5) 0.6579(4) 0.54060(15) 0.0251(12) Uani 1 1 d . . . . .
H2 H 0.5516 0.7245 0.5335 0.030 Uiso 1 1 calc R U . . .
C3 C 0.6777(6) 0.6081(4) 0.51607(16) 0.0291(13) Uani 1 1 d . . . . .
H3 H 0.7279 0.6409 0.4922 0.035 Uiso 1 1 calc R U . . .
C4 C 0.7073(5) 0.5114(4) 0.52623(15) 0.0254(12) Uani 1 1 d . . . . .
H4 H 0.7777 0.4765 0.5095 0.030 Uiso 1 1 calc R U . . .
C5 C 0.6328(5) 0.4651(3) 0.56141(15) 0.0184(11) Uani 1 1 d . . . . .
C6 C 0.6581(5) 0.3591(4) 0.57271(16) 0.0237(12) Uani 1 1 d . . . . .
H6A H 0.6011 0.3163 0.5522 0.028 Uiso 1 1 calc R U . . .
H6B H 0.7590 0.3427 0.5682 0.028 Uiso 1 1 calc R U . . .
C7 C 0.3456(5) 0.2982(4) 0.71517(16) 0.0242(12) Uani 1 1 d . . . . .
H7 H 0.2964 0.2690 0.6901 0.029 Uiso 1 1 calc R U . . .
C8 C 0.3238(6) 0.2609(4) 0.75875(15) 0.0264(12) Uani 1 1 d . . . . .
H8 H 0.2591 0.2083 0.7638 0.032 Uiso 1 1 calc R U . . .
C9 C 0.3981(6) 0.3015(4) 0.79487(16) 0.0311(13) Uani 1 1 d . . . . .
H9 H 0.3867 0.2764 0.8252 0.037 Uiso 1 1 calc R U . . .
C10 C 0.4891(5) 0.3790(4) 0.78655(16) 0.0261(12) Uani 1 1 d . . . . .
H10 H 0.5405 0.4084 0.8111 0.031 Uiso 1 1 calc R U . . .
C11 C 0.5044(5) 0.4134(3) 0.74177(15) 0.0179(11) Uani 1 1 d . . . . .
C12 C 0.6016(5) 0.4995(4) 0.73205(15) 0.0255(12) Uani 1 1 d . . . . .
H12A H 0.5758 0.5561 0.7519 0.031 Uiso 1 1 calc R U . . .
H12B H 0.7002 0.4806 0.7391 0.031 Uiso 1 1 calc R U . . .
H102 H 0.680(3) 0.548(3) 0.6723(14) 0.029(14) Uiso 1 1 d D . . . .
H111 H 0.221(3) 0.368(4) 0.6026(17) 0.057(19) Uiso 1 1 d D . . . .
H101 H 0.614(7) 0.2739(19) 0.6302(17) 0.07(2) Uiso 1 1 d D . . . .
H222 H 0.327(11) 0.287(5) 0.589(2) 0.17(4) Uiso 1 1 d 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 O3 2.064(3) . ?
Zn1 N1 2.069(4) . ?
Zn1 N2 2.080(4) . ?
Zn1 O2 2.167(3) . ?
Zn1 O1 2.172(3) . ?
Zn1 Cl1 2.4977(13) . ?
Zn2 Cl4 2.2405(13) . ?
Zn2 Cl3 2.2414(14) . ?
Zn2 Cl2 2.2872(13) . ?
Zn2 Cl1 2.3284(12) . ?
O1 C6 1.430(5) . ?
O1 H101 0.98(2) . ?
O2 C12 1.415(5) . ?
O2 H102 0.964(19) . ?
O3 H111 0.97(2) . ?
O3 H222 0.99(2) . ?
N1 C1 1.344(6) . ?
N1 C5 1.346(6) . ?
N2 C11 1.333(6) . ?
N2 C7 1.346(6) . ?
C1 C2 1.365(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.370(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.491(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.377(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.377(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.511(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?

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
O3 Zn1 N1 101.87(14) . . ?
O3 Zn1 N2 93.98(14) . . ?
N1 Zn1 N2 160.97(15) . . ?
O3 Zn1 O2 170.17(13) . . ?
N1 Zn1 O2 87.57(13) . . ?
N2 Zn1 O2 76.25(13) . . ?
O3 Zn1 O1 86.54(14) . . ?
N1 Zn1 O1 76.99(14) . . ?
N2 Zn1 O1 93.71(13) . . ?
O2 Zn1 O1 93.03(13) . . ?
O3 Zn1 Cl1 91.29(11) . . ?
N1 Zn1 Cl1 97.01(11) . . ?
N2 Zn1 Cl1 93.06(11) . . ?
O2 Zn1 Cl1 90.23(10) . . ?
O1 Zn1 Cl1 173.02(9) . . ?
Cl4 Zn2 Cl3 112.57(5) . . ?
Cl4 Zn2 Cl2 110.31(5) . . ?
Cl3 Zn2 Cl2 112.49(5) . . ?
Cl4 Zn2 Cl1 108.70(5) . . ?
Cl3 Zn2 Cl1 107.83(5) . . ?
Cl2 Zn2 Cl1 104.52(5) . . ?
Zn2 Cl1 Zn1 119.47(5) . . ?
C6 O1 Zn1 112.4(3) . . ?
C6 O1 H101 117(3) . . ?
Zn1 O1 H101 117(4) . . ?
C12 O2 Zn1 117.2(3) . . ?
C12 O2 H102 113(3) . . ?
Zn1 O2 H102 118(3) . . ?
Zn1 O3 H111 116(4) . . ?
Zn1 O3 H222 133(6) . . ?
H111 O3 H222 103(6) . . ?
C1 N1 C5 118.6(4) . . ?
C1 N1 Zn1 124.6(3) . . ?
C5 N1 Zn1 116.5(3) . . ?
C11 N2 C7 118.3(4) . . ?
C11 N2 Zn1 118.6(3) . . ?
C7 N2 Zn1 122.9(3) . . ?
N1 C1 C2 123.1(5) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C1 C2 C3 118.2(5) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C4 C3 C2 119.9(5) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 118.9(5) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.3(4) . . ?
N1 C5 C6 117.9(4) . . ?
C4 C5 C6 120.8(4) . . ?
O1 C6 C5 108.5(4) . . ?
O1 C6 H6A 110.0 . . ?
C5 C6 H6A 110.0 . . ?
O1 C6 H6B 110.0 . . ?
C5 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
N2 C7 C8 122.9(5) . . ?
N2 C7 H7 118.6 . . ?
C8 C7 H7 118.6 . . ?
C9 C8 C7 118.4(5) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C8 C9 C10 119.3(5) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C9 C10 C11 119.0(5) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
N2 C11 C10 122.1(5) . . ?
N2 C11 C12 118.1(4) . . ?
C10 C11 C12 119.8(4) . . ?
O2 C12 C11 109.7(4) . . ?
O2 C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 . . ?
O2 C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?

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
C5 N1 C1 C2 -0.1(7) . . . . ?
Zn1 N1 C1 C2 173.5(4) . . . . ?
N1 C1 C2 C3 -1.3(7) . . . . ?
C1 C2 C3 C4 1.4(7) . . . . ?
C2 C3 C4 C5 -0.2(7) . . . . ?
C1 N1 C5 C4 1.3(7) . . . . ?
Zn1 N1 C5 C4 -172.8(3) . . . . ?
C1 N1 C5 C6 -178.0(4) . . . . ?
Zn1 N1 C5 C6 8.0(5) . . . . ?
C3 C4 C5 N1 -1.2(7) . . . . ?
C3 C4 C5 C6 178.1(4) . . . . ?
Zn1 O1 C6 C5 30.1(4) . . . . ?
N1 C5 C6 O1 -25.6(6) . . . . ?
C4 C5 C6 O1 155.1(4) . . . . ?
C11 N2 C7 C8 1.3(7) . . . . ?
Zn1 N2 C7 C8 -173.3(4) . . . . ?
N2 C7 C8 C9 -1.7(8) . . . . ?
C7 C8 C9 C10 1.3(8) . . . . ?
C8 C9 C10 C11 -0.6(8) . . . . ?
C7 N2 C11 C10 -0.5(7) . . . . ?
Zn1 N2 C11 C10 174.3(4) . . . . ?
C7 N2 C11 C12 -179.2(4) . . . . ?
Zn1 N2 C11 C12 -4.4(6) . . . . ?
C9 C10 C11 N2 0.2(8) . . . . ?
C9 C10 C11 C12 178.9(5) . . . . ?
Zn1 O2 C12 C11 -1.9(5) . . . . ?
N2 C11 C12 O2 4.0(6) . . . . ?
C10 C11 C12 O2 -174.7(4) . . . . ?

_refine_diff_density_max         0.531
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.103

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1050187'
_audit_update_record             
;
2015-02-18 deposited with the CCDC.
2015-12-16 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         ?
_chemical_formula_sum            'C7 H9 Cl2 N O Zn'
_chemical_formula_weight         259.42

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.468(7)
_cell_length_b                   8.1058(6)
_cell_length_c                   10.993(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.69(4)
_cell_angle_gamma                90
_cell_volume                     924.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1759
_cell_measurement_theta_min      3.1317
_cell_measurement_theta_max      32.4049

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.864
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    3.182
_shelx_estimated_absorpt_T_min   0.528
_shelx_estimated_absorpt_T_max   0.647
_exptl_absorpt_correction_T_min  0.36910
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET)
(compiled Apr 21 2008,18:23:10)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;




_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3961
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.132
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1627
_reflns_number_gt                1387
_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       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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     
'w=1/[σ²(Fo²)+(0.0529P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1627
_refine_ls_number_parameters     113
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0824
_refine_ls_wR_factor_gt          0.0802
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_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 0.56072(3) 0.08328(5) 0.86879(3) 0.01282(16) Uani 1 1 d . . . . .
Cl1 Cl 0.77434(7) 0.05306(11) 0.86826(8) 0.0163(2) Uani 1 1 d . . . . .
Cl2 Cl 0.48281(7) 0.20003(11) 1.03246(7) 0.0143(2) Uani 1 1 d . . . . .
O1 O 0.5513(3) 0.3235(4) 0.7734(2) 0.0195(6) Uani 1 1 d . . . . .
N1 N 0.4512(2) 0.0077(4) 0.7129(2) 0.0114(6) Uani 1 1 d . . . . .
C1 C 0.4807(3) -0.1341(4) 0.6598(3) 0.0134(7) Uani 1 1 d . . . . .
H1 H 0.5494 -0.1993 0.6996 0.016 Uiso 1 1 calc R U . . .
C2 C 0.4156(3) -0.1889(5) 0.5500(3) 0.0153(8) Uani 1 1 d . . . . .
H2 H 0.4399 -0.2889 0.5143 0.018 Uiso 1 1 calc R U . . .
C3 C 0.3148(3) -0.0964(5) 0.4929(3) 0.0169(8) Uani 1 1 d . . . . .
H3 H 0.2670 -0.1329 0.4182 0.020 Uiso 1 1 calc R U . . .
C4 C 0.2842(3) 0.0500(5) 0.5460(3) 0.0157(8) Uani 1 1 d . . . . .
H4 H 0.2155 0.1159 0.5070 0.019 Uiso 1 1 calc R U . . .
C5 C 0.3532(3) 0.1019(5) 0.6564(3) 0.0132(7) Uani 1 1 d . . . . .
C6 C 0.3258(3) 0.2603(4) 0.7179(3) 0.0140(8) Uani 1 1 d . . . . .
H6A H 0.3148 0.2369 0.8042 0.017 Uiso 1 1 calc R U . . .
H6B H 0.2435 0.3060 0.6767 0.017 Uiso 1 1 calc R U . . .
C7 C 0.4309(3) 0.3896(5) 0.7159(3) 0.0185(8) Uani 1 1 d . . . . .
H7A H 0.4383 0.4208 0.6300 0.022 Uiso 1 1 calc R U . . .
H7B H 0.4087 0.4896 0.7602 0.022 Uiso 1 1 calc R U . . .
H101 H 0.602(4) 0.372(5) 0.758(4) 0.015(13) Uiso 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 2.025(3) . ?
Zn1 O1 2.208(3) . ?
Zn1 Cl1 2.2504(17) . ?
Zn1 Cl2 2.2782(11) . ?
Zn1 Cl2 2.6062(10) 3_657 ?
Cl2 Zn1 2.6062(10) 3_657 ?
O1 C7 1.436(4) . ?
O1 H101 0.70(4) . ?
N1 C1 1.344(5) . ?
N1 C5 1.360(4) . ?
C1 C2 1.378(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.375(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.497(5) . ?
C6 C7 1.522(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?

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 83.13(11) . . ?
N1 Zn1 Cl1 114.53(9) . . ?
O1 Zn1 Cl1 94.37(8) . . ?
N1 Zn1 Cl2 124.89(9) . . ?
O1 Zn1 Cl2 90.62(8) . . ?
Cl1 Zn1 Cl2 120.54(5) . . ?
N1 Zn1 Cl2 88.57(8) . 3_657 ?
O1 Zn1 Cl2 167.39(7) . 3_657 ?
Cl1 Zn1 Cl2 97.72(4) . 3_657 ?
Cl2 Zn1 Cl2 86.33(4) . 3_657 ?
Zn1 Cl2 Zn1 93.67(4) . 3_657 ?
C7 O1 Zn1 121.3(2) . . ?
C7 O1 H101 109(3) . . ?
Zn1 O1 H101 129(3) . . ?
C1 N1 C5 119.0(3) . . ?
C1 N1 Zn1 119.3(2) . . ?
C5 N1 Zn1 121.6(2) . . ?
N1 C1 C2 122.7(3) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 118.9(3) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
N1 C5 C4 120.1(3) . . ?
N1 C5 C6 117.0(3) . . ?
C4 C5 C6 123.0(3) . . ?
C5 C6 C7 113.7(3) . . ?
C5 C6 H6A 108.8 . . ?
C7 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
C7 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
O1 C7 C6 109.3(3) . . ?
O1 C7 H7A 109.8 . . ?
C6 C7 H7A 109.8 . . ?
O1 C7 H7B 109.8 . . ?
C6 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?

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
C5 N1 C1 C2 -0.2(5) . . . . ?
Zn1 N1 C1 C2 -176.1(3) . . . . ?
N1 C1 C2 C3 -1.0(5) . . . . ?
C1 C2 C3 C4 1.5(5) . . . . ?
C2 C3 C4 C5 -0.9(5) . . . . ?
C1 N1 C5 C4 0.8(5) . . . . ?
Zn1 N1 C5 C4 176.7(2) . . . . ?
C1 N1 C5 C6 -178.8(3) . . . . ?
Zn1 N1 C5 C6 -2.9(4) . . . . ?
C3 C4 C5 N1 -0.3(5) . . . . ?
C3 C4 C5 C6 179.3(3) . . . . ?
N1 C5 C6 C7 69.1(4) . . . . ?
C4 C5 C6 C7 -110.5(4) . . . . ?
Zn1 O1 C7 C6 -7.8(4) . . . . ?
C5 C6 C7 O1 -57.5(4) . . . . ?

_refine_diff_density_max         0.868
_refine_diff_density_min         -1.079
_refine_diff_density_rms         0.144

