# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_csl5
_database_code_depnum_ccdc_archive 'CCDC 833810'
_audit_update_record             
;
2011-07-12 deposited with the CCDC.
2015-03-23 downloaded from the CCDC.
;
#TrackingRef 'CSL5.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            L5
_chemical_melting_point          117.6
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H24 N4 O2'
_chemical_formula_weight         352.43

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C2/c '

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

_cell_length_a                   16.301
_cell_length_b                   9.193
_cell_length_c                   13.044
_cell_angle_alpha                90.00
_cell_angle_beta                 100.67
_cell_angle_gamma                90.00
_cell_volume                     1921.0
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4149
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      29.18

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9741
_exptl_absorpt_correction_T_max  0.9853
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4149
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0457
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         29.18
_reflns_number_total             2208
_reflns_number_gt                1137
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Smart'
_computing_cell_refinement       'Bruker Smart'
_computing_data_reduction        'Bruker Smart'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  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)+(0.1066P)²+1.5064P] 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         2208
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1448
_refine_ls_R_factor_gt           0.0785
_refine_ls_wR_factor_ref         0.2500
_refine_ls_wR_factor_gt          0.2007
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.33314(15) -0.1168(2) -0.05796(18) 0.0743(8) Uani 1 1 d . . .
N1 N 0.36640(15) 0.1033(2) 0.02462(19) 0.0577(7) Uani 1 1 d . . .
N2 N 0.41420(17) 0.4086(3) 0.1895(2) 0.0649(8) Uani 1 1 d . . .
C1 C 0.4025(3) -0.0973(5) -0.1076(3) 0.0918(13) Uani 1 1 d . . .
H1B H 0.4057 -0.1772 -0.1541 0.138 Uiso 1 1 calc R . .
H1C H 0.4527 -0.0934 -0.0559 0.138 Uiso 1 1 calc R . .
H1D H 0.3962 -0.0081 -0.1465 0.138 Uiso 1 1 calc R . .
C2 C 0.31918(19) -0.0135(3) 0.0109(2) 0.0584(8) Uani 1 1 d . . .
C3 C 0.2550(2) -0.0425(4) 0.0643(3) 0.0720(10) Uani 1 1 d . . .
H3A H 0.2234 -0.1271 0.0519 0.086 Uiso 1 1 calc R . .
C4 C 0.2399(2) 0.0569(4) 0.1350(3) 0.0806(11) Uani 1 1 d . . .
H4A H 0.1975 0.0410 0.1726 0.097 Uiso 1 1 calc R . .
C5 C 0.2876(2) 0.1823(4) 0.1512(3) 0.0717(10) Uani 1 1 d . . .
H5A H 0.2770 0.2525 0.1984 0.086 Uiso 1 1 calc R . .
C6 C 0.3507(2) 0.2007(3) 0.0964(2) 0.0566(8) Uani 1 1 d . . .
C7 C 0.4077(2) 0.3265(3) 0.1114(2) 0.0597(9) Uani 1 1 d . . .
H7A H 0.4401 0.3459 0.0612 0.072 Uiso 1 1 calc R . .
C8 C 0.4714(2) 0.5324(3) 0.1960(3) 0.0682(10) Uani 1 1 d . . .
H8A H 0.5053 0.5239 0.1416 0.082 Uiso 1 1 calc R . .
C9 C 0.4205(3) 0.6726(4) 0.1800(3) 0.0875(13) Uani 1 1 d . . .
H9A H 0.3877 0.6735 0.1099 0.105 Uiso 1 1 calc R . .
H9B H 0.3821 0.6747 0.2286 0.105 Uiso 1 1 calc R . .
C10 C 0.4741(3) 0.8053(4) 0.1954(3) 0.0874(13) Uani 1 1 d . . .
H10A H 0.4393 0.8916 0.1854 0.105 Uiso 1 1 calc R . .
H10B H 0.5106 0.8069 0.1445 0.105 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
O1 C2 1.355(4) . ?
O1 C1 1.414(4) . ?
N1 C2 1.314(4) . ?
N1 C6 1.354(4) . ?
N2 C7 1.256(4) . ?
N2 C8 1.464(4) . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H1D 0.9600 . ?
C2 C3 1.386(5) . ?
C3 C4 1.352(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.385(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.367(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.474(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.526(5) . ?
C8 C8 1.540(6) 2_655 ?
C8 H8A 0.9800 . ?
C9 C10 1.492(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C10 1.515(7) 2_655 ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

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
C2 O1 C1 117.4(2) . . ?
C2 N1 C6 117.0(3) . . ?
C7 N2 C8 118.1(3) . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C1 H1D 109.5 . . ?
H1B C1 H1D 109.5 . . ?
H1C C1 H1D 109.5 . . ?
N1 C2 O1 119.8(3) . . ?
N1 C2 C3 124.5(3) . . ?
O1 C2 C3 115.7(3) . . ?
C4 C3 C2 117.5(3) . . ?
C4 C3 H3A 121.2 . . ?
C2 C3 H3A 121.2 . . ?
C3 C4 C5 119.9(4) . . ?
C3 C4 H4A 120.1 . . ?
C5 C4 H4A 120.1 . . ?
C6 C5 C4 118.6(3) . . ?
C6 C5 H5A 120.7 . . ?
C4 C5 H5A 120.7 . . ?
N1 C6 C5 122.4(3) . . ?
N1 C6 C7 114.5(3) . . ?
C5 C6 C7 123.0(3) . . ?
N2 C7 C6 122.3(3) . . ?
N2 C7 H7A 118.8 . . ?
C6 C7 H7A 118.8 . . ?
N2 C8 C9 109.0(3) . . ?
N2 C8 C8 108.9(3) . 2_655 ?
C9 C8 C8 110.3(3) . 2_655 ?
N2 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C8 C8 H8A 109.5 2_655 . ?
C10 C9 C8 112.5(3) . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C10 109.7(3) . 2_655 ?
C9 C10 H10A 109.7 . . ?
C10 C10 H10A 109.7 2_655 . ?
C9 C10 H10B 109.7 . . ?
C10 C10 H10B 109.7 2_655 . ?
H10A C10 H10B 108.2 . . ?

_diffrn_measured_fraction_theta_max 0.854
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_hg
_database_code_depnum_ccdc_archive 'CCDC 833811'
_audit_update_record             
;
2011-07-12 deposited with the CCDC.
2015-03-23 downloaded from the CCDC.
;
#TrackingRef 'HG.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            Hg2
_chemical_melting_point          223
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H21 Cl6 Hg2 N4'
_chemical_formula_weight         919.28

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   9.247
_cell_length_b                   15.775
_cell_length_c                   17.778
_cell_angle_alpha                90.00
_cell_angle_beta                 90.75
_cell_angle_gamma                90.00
_cell_volume                     2593.1
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    12478
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1700
_exptl_absorpt_coefficient_mu    12.460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1088
_exptl_absorpt_correction_T_max  0.2126
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12478
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_sigmaI/netI    0.0493
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.41
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2957
_reflns_number_gt                2625
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Smart'
_computing_cell_refinement       'Bruker Smart'
_computing_data_reduction        'Bruker Smart'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  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)+(0.0474P)²+16.5377P] 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         2957
_refine_ls_number_parameters     141
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0996
_refine_ls_wR_factor_gt          0.0964
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.033
_refine_ls_shift/su_mean         0.004

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
Hg1 Hg 0.34085(2) 0.227414(18) 0.596077(14) 0.04118(12) Uani 1 1 d . . .
Cl1 Cl 0.13216(19) 0.20994(14) 0.67098(11) 0.0538(5) Uani 1 1 d . . .
Cl2 Cl 0.32819(16) 0.13064(11) 0.48247(9) 0.0425(3) Uani 1 1 d . . .
Cl3 Cl 0.4708(10) 0.4640(5) 0.6754(3) 0.225(3) Uani 1 1 d U . .
N1 N 0.5401(5) 0.3047(3) 0.5651(3) 0.0323(10) Uani 1 1 d . . .
N2 N 0.5508(5) 0.1752(3) 0.6712(3) 0.0325(10) Uani 1 1 d . . .
C1 C 0.5395(7) 0.3659(4) 0.5139(4) 0.0414(14) Uani 1 1 d . . .
H1A H 0.4534 0.3788 0.4889 0.050 Uiso 1 1 calc R . .
C2 C 0.6632(7) 0.4113(5) 0.4966(4) 0.0453(15) Uani 1 1 d . . .
H2A H 0.6595 0.4554 0.4620 0.054 Uiso 1 1 calc R . .
C3 C 0.7911(7) 0.3899(5) 0.5316(4) 0.0478(16) Uani 1 1 d . . .
H3A H 0.8758 0.4185 0.5199 0.057 Uiso 1 1 calc R . .
C4 C 0.7933(7) 0.3259(5) 0.5839(4) 0.0427(14) Uani 1 1 d . . .
H4A H 0.8793 0.3107 0.6080 0.051 Uiso 1 1 calc R . .
C5 C 0.6662(6) 0.2845(4) 0.6000(4) 0.0327(12) Uani 1 1 d . . .
C6 C 0.6656(7) 0.2153(4) 0.6554(4) 0.0360(13) Uani 1 1 d . . .
H6A H 0.7518 0.2005 0.6796 0.043 Uiso 1 1 calc R . .
C7 C 0.5622(7) 0.1025(4) 0.7214(3) 0.0339(12) Uani 1 1 d . . .
H7A H 0.6553 0.1041 0.7483 0.041 Uiso 1 1 calc R . .
C8 C 0.5526(9) 0.0216(4) 0.6734(4) 0.0491(17) Uani 1 1 d . . .
H8A H 0.4626 0.0218 0.6448 0.059 Uiso 1 1 calc R . .
H8B H 0.6316 0.0209 0.6380 0.059 Uiso 1 1 calc R . .
C9 C 0.5598(11) -0.0575(5) 0.7219(5) 0.061(2) Uani 1 1 d . . .
H9A H 0.5518 -0.1074 0.6902 0.074 Uiso 1 1 calc R . .
H9B H 0.6524 -0.0597 0.7481 0.074 Uiso 1 1 calc R . .
C10 C 0.5000 0.5199(13) 0.7500 0.105(6) Uani 1 2 d S . .
H10A H 0.4193 0.5555 0.7621 0.126 Uiso 0.50 1 d PR . .


_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
Hg1 N1 2.283(5) . ?
Hg1 Cl1 2.3749(17) . ?
Hg1 N2 2.482(5) . ?
Hg1 Cl2 2.5333(16) . ?
Cl3 C10 1.613(13) . ?
N1 C1 1.327(8) . ?
N1 C5 1.352(8) . ?
N2 C6 1.270(8) . ?
N2 C7 1.456(8) . ?
C1 C2 1.387(9) . ?
C1 H1A 0.9300 . ?
C2 C3 1.370(10) . ?
C2 H2A 0.9300 . ?
C3 C4 1.372(10) . ?
C3 H3A 0.9300 . ?
C4 C5 1.379(9) . ?
C4 H4A 0.9300 . ?
C5 C6 1.470(9) . ?
C6 H6A 0.9300 . ?
C7 C8 1.537(9) . ?
C7 C7 1.545(12) 2_656 ?
C7 H7A 0.9800 . ?
C8 C9 1.518(11) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C9 1.500(18) 2_656 ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 Cl3 1.613(13) 2_656 ?
C10 H10A 0.9600 . ?

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 Hg1 Cl1 149.50(14) . . ?
N1 Hg1 N2 71.27(17) . . ?
Cl1 Hg1 N2 107.18(12) . . ?
N1 Hg1 Cl2 99.12(13) . . ?
Cl1 Hg1 Cl2 110.34(7) . . ?
N2 Hg1 Cl2 104.87(12) . . ?
C1 N1 C5 118.9(5) . . ?
C1 N1 Hg1 123.9(4) . . ?
C5 N1 Hg1 117.2(4) . . ?
C6 N2 C7 118.2(5) . . ?
C6 N2 Hg1 111.5(4) . . ?
C7 N2 Hg1 129.8(4) . . ?
N1 C1 C2 122.1(6) . . ?
N1 C1 H1A 118.9 . . ?
C2 C1 H1A 118.9 . . ?
C3 C2 C1 118.8(6) . . ?
C3 C2 H2A 120.6 . . ?
C1 C2 H2A 120.6 . . ?
C2 C3 C4 119.6(6) . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 H3A 120.2 . . ?
C3 C4 C5 119.0(6) . . ?
C3 C4 H4A 120.5 . . ?
C5 C4 H4A 120.5 . . ?
N1 C5 C4 121.7(6) . . ?
N1 C5 C6 118.2(5) . . ?
C4 C5 C6 120.1(6) . . ?
N2 C6 C5 121.8(6) . . ?
N2 C6 H6A 119.1 . . ?
C5 C6 H6A 119.1 . . ?
N2 C7 C8 108.1(5) . . ?
N2 C7 C7 110.8(4) . 2_656 ?
C8 C7 C7 109.1(5) . 2_656 ?
N2 C7 H7A 109.6 . . ?
C8 C7 H7A 109.6 . . ?
C7 C7 H7A 109.6 2_656 . ?
C9 C8 C7 111.4(6) . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C9 C9 C8 110.5(6) 2_656 . ?
C9 C9 H9A 109.5 2_656 . ?
C8 C9 H9A 109.5 . . ?
C9 C9 H9B 109.5 2_656 . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
Cl3 C10 Cl3 113.7(14) . 2_656 ?
Cl3 C10 H10A 112.5 . . ?
Cl3 C10 H10A 104.9 2_656 . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.682
_refine_diff_density_min         -2.393
_refine_diff_density_rms         0.187
####################################################################### 
# 
# 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_zn
_database_code_depnum_ccdc_archive 'CCDC 833812'
_audit_update_record             
;
2011-07-12 deposited with the CCDC.
2015-03-23 downloaded from the CCDC.
;
#TrackingRef 'ZN.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            Zn
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H28 Cl4 N4 O Zn2'
_chemical_formula_weight         625.01

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                   9.0940(18)
_cell_length_b                   9.6731(19)
_cell_length_c                   15.980(3)
_cell_angle_alpha                95.63(3)
_cell_angle_beta                 91.68(3)
_cell_angle_gamma                109.86(3)
_cell_volume                     1312.7(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    12938
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             636
_exptl_absorpt_coefficient_mu    2.255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5415
_exptl_absorpt_correction_T_max  0.6250
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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 P4'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12938
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0473
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5951
_reflns_number_gt                4292
_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, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  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)+(0.0563P)²+0.8199P] 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         5951
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1260
_refine_ls_wR_factor_gt          0.1111
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 0.28310(5) 0.34871(5) 0.37368(3) 0.04590(14) Uani 1 1 d . . .
Zn2 Zn 0.05339(5) 0.28862(5) 0.09011(3) 0.04504(14) Uani 1 1 d . . .
Cl1 Cl 0.49364(13) 0.43651(17) 0.30398(9) 0.0787(4) Uani 1 1 d . . .
Cl2 Cl 0.29204(14) 0.19837(17) 0.46960(9) 0.0797(4) Uani 1 1 d . . .
Cl3 Cl 0.08964(15) 0.51615(13) 0.14824(8) 0.0705(3) Uani 1 1 d . . .
Cl4 Cl -0.18908(12) 0.14308(16) 0.04880(7) 0.0698(3) Uani 1 1 d . . .
O1 O 0.4782(11) 0.0154(11) 0.3552(6) 0.225(4) Uani 1 1 d . . .
H1B H 0.5634 0.0587 0.3333 0.270 Uiso 1 1 d R . .
N1 N 0.2066(4) 0.5182(4) 0.41524(19) 0.0472(7) Uani 1 1 d . . .
N2 N 0.0643(3) 0.2742(3) 0.31108(16) 0.0370(6) Uani 1 1 d . . .
N3 N 0.1722(3) 0.1711(3) 0.14769(16) 0.0374(6) Uani 1 1 d . . .
N4 N 0.2307(3) 0.3110(4) 0.01125(18) 0.0436(7) Uani 1 1 d . . .
C1 C 0.2842(5) 0.6399(5) 0.4663(3) 0.0588(11) Uani 1 1 d . . .
H1A H 0.3848 0.6535 0.4881 0.071 Uiso 1 1 calc R . .
C2 C 0.2182(6) 0.7468(5) 0.4876(3) 0.0641(12) Uani 1 1 d . . .
H2A H 0.2750 0.8318 0.5229 0.077 Uiso 1 1 calc R . .
C3 C 0.0726(6) 0.7285(5) 0.4578(3) 0.0621(12) Uani 1 1 d . . .
H3A H 0.0277 0.7998 0.4729 0.075 Uiso 1 1 calc R . .
C4 C -0.0108(5) 0.6020(4) 0.4039(2) 0.0497(9) Uani 1 1 d . . .
H4A H -0.1121 0.5869 0.3829 0.060 Uiso 1 1 calc R . .
C5 C 0.0609(4) 0.4987(4) 0.3824(2) 0.0398(7) Uani 1 1 d . . .
C6 C -0.0166(4) 0.3588(4) 0.3253(2) 0.0394(8) Uani 1 1 d . . .
C7 C -0.1810(4) 0.3282(5) 0.2901(3) 0.0556(10) Uani 1 1 d . . .
H7A H -0.2165 0.2355 0.2547 0.083 Uiso 1 1 calc R . .
H7B H -0.1831 0.4060 0.2576 0.083 Uiso 1 1 calc R . .
H7C H -0.2486 0.3237 0.3356 0.083 Uiso 1 1 calc R . .
C8 C -0.0087(4) 0.1253(4) 0.2636(2) 0.0388(7) Uani 1 1 d . . .
H8A H -0.0904 0.1276 0.2230 0.047 Uiso 1 1 calc R . .
C9 C -0.0841(5) 0.0180(4) 0.3273(2) 0.0475(9) Uani 1 1 d . . .
H9A H -0.0059 0.0254 0.3718 0.057 Uiso 1 1 calc R . .
H9B H -0.1666 0.0465 0.3528 0.057 Uiso 1 1 calc R . .
C10 C -0.1520(5) -0.1402(5) 0.2877(3) 0.0557(10) Uani 1 1 d . . .
H10A H -0.2377 -0.1507 0.2472 0.067 Uiso 1 1 calc R . .
H10B H -0.1931 -0.2044 0.3308 0.067 Uiso 1 1 calc R . .
C11 C -0.0275(5) -0.1855(5) 0.2439(3) 0.0564(10) Uani 1 1 d . . .
H11A H -0.0732 -0.2864 0.2170 0.068 Uiso 1 1 calc R . .
H11B H 0.0546 -0.1820 0.2851 0.068 Uiso 1 1 calc R . .
C12 C 0.0427(5) -0.0819(4) 0.1777(2) 0.0524(10) Uani 1 1 d . . .
H12A H 0.1224 -0.1123 0.1504 0.063 Uiso 1 1 calc R . .
H12B H -0.0388 -0.0901 0.1350 0.063 Uiso 1 1 calc R . .
C13 C 0.1143(4) 0.0773(4) 0.2159(2) 0.0395(7) Uani 1 1 d . . .
H13A H 0.2026 0.0871 0.2555 0.047 Uiso 1 1 calc R . .
C14 C 0.4135(5) 0.1044(6) 0.1431(3) 0.0663(13) Uani 1 1 d . . .
H14A H 0.3780 0.0578 0.1926 0.099 Uiso 1 1 calc R . .
H14B H 0.5145 0.1796 0.1560 0.099 Uiso 1 1 calc R . .
H14C H 0.4210 0.0318 0.0995 0.099 Uiso 1 1 calc R . .
C15 C 0.2994(4) 0.1732(4) 0.1134(2) 0.0436(8) Uani 1 1 d . . .
C16 C 0.3355(4) 0.2515(4) 0.0363(2) 0.0437(8) Uani 1 1 d . . .
C17 C 0.4664(5) 0.2620(5) -0.0089(3) 0.0559(10) Uani 1 1 d . . .
H17A H 0.5382 0.2196 0.0085 0.067 Uiso 1 1 calc R . .
C18 C 0.4890(5) 0.3354(5) -0.0796(3) 0.0638(12) Uani 1 1 d . . .
H18A H 0.5765 0.3435 -0.1101 0.077 Uiso 1 1 calc R . .
C19 C 0.3826(6) 0.3959(5) -0.1043(3) 0.0653(12) Uani 1 1 d . . .
H19A H 0.3957 0.4449 -0.1523 0.078 Uiso 1 1 calc R . .
C20 C 0.2542(5) 0.3839(5) -0.0571(3) 0.0568(10) Uani 1 1 d . . .
H20A H 0.1826 0.4274 -0.0733 0.068 Uiso 1 1 calc R . .
C21 C 0.4509(11) -0.1297(12) 0.3131(7) 0.167(5) Uani 1 1 d . . .
H21C H 0.3471 -0.1681 0.2861 0.201 Uiso 1 1 calc R . .
H21A H 0.4613 -0.1936 0.3534 0.201 Uiso 1 1 calc R . .
H21B H 0.5261 -0.1245 0.2715 0.201 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 2.050(3) . ?
Zn1 N2 2.061(3) . ?
Zn1 Cl1 2.1985(14) . ?
Zn1 Cl2 2.2319(14) . ?
Zn2 N4 2.042(3) . ?
Zn2 N3 2.070(3) . ?
Zn2 Cl4 2.2142(15) . ?
Zn2 Cl3 2.2144(14) . ?
O1 C21 1.432(12) . ?
O1 H1B 0.8499 . ?
N1 C1 1.328(5) . ?
N1 C5 1.355(4) . ?
N2 C6 1.283(4) . ?
N2 C8 1.482(5) . ?
N3 C15 1.289(4) . ?
N3 C13 1.481(4) . ?
N4 C16 1.339(5) . ?
N4 C20 1.341(5) . ?
C1 C2 1.382(6) . ?
C1 H1A 0.9300 . ?
C2 C3 1.342(7) . ?
C2 H2A 0.9300 . ?
C3 C4 1.392(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.389(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.495(5) . ?
C6 C7 1.502(5) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.533(5) . ?
C8 C13 1.543(4) . ?
C8 H8A 0.9800 . ?
C9 C10 1.506(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.512(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.532(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.510(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9800 . ?
C14 C15 1.499(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.496(5) . ?
C16 C17 1.391(5) . ?
C17 C18 1.375(6) . ?
C17 H17A 0.9300 . ?
C18 C19 1.358(7) . ?
C18 H18A 0.9300 . ?
C19 C20 1.387(6) . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?
C21 H21C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?

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 N2 80.43(12) . . ?
N1 Zn1 Cl1 109.19(10) . . ?
N2 Zn1 Cl1 120.05(8) . . ?
N1 Zn1 Cl2 115.01(10) . . ?
N2 Zn1 Cl2 109.72(9) . . ?
Cl1 Zn1 Cl2 117.09(6) . . ?
N4 Zn2 N3 80.25(11) . . ?
N4 Zn2 Cl4 120.65(9) . . ?
N3 Zn2 Cl4 110.30(9) . . ?
N4 Zn2 Cl3 105.03(10) . . ?
N3 Zn2 Cl3 117.33(9) . . ?
Cl4 Zn2 Cl3 117.90(6) . . ?
C21 O1 H1B 97.0 . . ?
C1 N1 C5 119.7(3) . . ?
C1 N1 Zn1 127.6(3) . . ?
C5 N1 Zn1 112.7(2) . . ?
C6 N2 C8 120.2(3) . . ?
C6 N2 Zn1 114.8(2) . . ?
C8 N2 Zn1 124.3(2) . . ?
C15 N3 C13 120.2(3) . . ?
C15 N3 Zn2 114.0(2) . . ?
C13 N3 Zn2 125.49(19) . . ?
C16 N4 C20 119.6(3) . . ?
C16 N4 Zn2 113.5(2) . . ?
C20 N4 Zn2 126.8(3) . . ?
N1 C1 C2 121.1(4) . . ?
N1 C1 H1A 119.5 . . ?
C2 C1 H1A 119.4 . . ?
C3 C2 C1 120.4(4) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
C2 C3 C4 119.4(4) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C5 C4 C3 118.5(4) . . ?
C5 C4 H4A 120.8 . . ?
C3 C4 H4A 120.8 . . ?
N1 C5 C4 120.8(4) . . ?
N1 C5 C6 115.7(3) . . ?
C4 C5 C6 123.4(3) . . ?
N2 C6 C5 116.3(3) . . ?
N2 C6 C7 125.7(3) . . ?
C5 C6 C7 118.0(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 C9 107.4(3) . . ?
N2 C8 C13 110.8(3) . . ?
C9 C8 C13 111.2(3) . . ?
N2 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
C13 C8 H8A 109.1 . . ?
C10 C9 C8 112.6(3) . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C11 110.2(3) . . ?
C9 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C10 C11 C12 110.3(3) . . ?
C10 C11 H11A 109.6 . . ?
C12 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
C12 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C13 C12 C11 112.0(3) . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
N3 C13 C12 108.8(3) . . ?
N3 C13 C8 110.6(3) . . ?
C12 C13 C8 110.0(3) . . ?
N3 C13 H13A 109.2 . . ?
C12 C13 H13A 109.2 . . ?
C8 C13 H13A 109.2 . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C15 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 C16 116.5(3) . . ?
N3 C15 C14 126.4(3) . . ?
C16 C15 C14 117.1(3) . . ?
N4 C16 C17 120.6(4) . . ?
N4 C16 C15 115.6(3) . . ?
C17 C16 C15 123.8(4) . . ?
C18 C17 C16 119.5(4) . . ?
C18 C17 H17A 120.2 . . ?
C16 C17 H17A 120.2 . . ?
C19 C18 C17 119.5(4) . . ?
C19 C18 H18A 120.3 . . ?
C17 C18 H18A 120.3 . . ?
C18 C19 C20 119.2(4) . . ?
C18 C19 H19A 120.4 . . ?
C20 C19 H19A 120.4 . . ?
N4 C20 C19 121.6(4) . . ?
N4 C20 H20A 119.2 . . ?
C19 C20 H20A 119.2 . . ?
O1 C21 H21C 109.5 . . ?
O1 C21 H21A 109.5 . . ?
H21C C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
H21C C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         1.284
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.082





####################################################################### 
# 
# 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_hg1
_database_code_depnum_ccdc_archive 'CCDC 933229'
_audit_update_record             
;
2013-04-10 deposited with the CCDC.
2015-03-23 downloaded from the CCDC.
;
#TrackingRef 'Hg1.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 Cl2 Hg N4'
_chemical_formula_weight         586.88

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 '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                   11.881(2)
_cell_length_b                   9.3930(19)
_cell_length_c                   17.817(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.76(3)
_cell_angle_gamma                90.00
_cell_volume                     1978.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    17608
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.970
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1124
_exptl_absorpt_coefficient_mu    8.063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1674
_exptl_absorpt_correction_T_max  0.4791
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            17608
_diffrn_reflns_av_R_equivalents  0.1041
_diffrn_reflns_av_sigmaI/netI    0.0972
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4381
_reflns_number_gt                2889
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.1469P)²+63.9307P] 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     SHELXL
_refine_ls_extinction_coef       0.0046(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4381
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1341
_refine_ls_R_factor_gt           0.1009
_refine_ls_wR_factor_ref         0.3512
_refine_ls_wR_factor_gt          0.3298
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_restrained_S_all      1.141
_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
Hg1 Hg 0.89080(9) 0.69225(9) 1.02165(5) 0.0612(5) Uani 1 1 d . . .
C1 C 0.592(3) 0.956(4) 0.7611(18) 0.087(9) Uani 1 1 d . . .
H1A H 0.5923 0.9900 0.7120 0.105 Uiso 1 1 calc R . .
C2 C 0.580(3) 0.814(3) 0.7699(18) 0.079(8) Uani 1 1 d . . .
H2A H 0.5687 0.7526 0.7286 0.095 Uiso 1 1 calc R . .
C3 C 0.585(3) 0.763(4) 0.843(2) 0.095(11) Uani 1 1 d . . .
H3A H 0.5810 0.6662 0.8524 0.115 Uiso 1 1 calc R . .
C4 C 0.595(3) 0.857(4) 0.901(2) 0.086(10) Uani 1 1 d . . .
H4A H 0.5964 0.8245 0.9501 0.104 Uiso 1 1 calc R . .
C5 C 0.6044(18) 1.005(3) 0.8860(12) 0.054(5) Uani 1 1 d . . .
C6 C 0.6262(18) 1.109(2) 0.9493(13) 0.050(5) Uani 1 1 d . . .
H6A H 0.6012 1.0663 0.9948 0.060 Uiso 1 1 calc R . .
C7 C 0.7530(18) 1.143(2) 0.9650(13) 0.048(5) Uani 1 1 d . . .
C8 C 0.558(2) 1.247(3) 0.933(2) 0.085(9) Uani 1 1 d . . .
H8A H 0.4791 1.2243 0.9234 0.128 Uiso 1 1 calc R . .
H8B H 0.5829 1.2930 0.8893 0.128 Uiso 1 1 calc R . .
H8C H 0.5696 1.3096 0.9755 0.128 Uiso 1 1 calc R . .
C9 C 0.8232(16) 1.0053(17) 0.9735(11) 0.040(4) Uani 1 1 d . . .
C10 C 0.8711(17) 0.947(2) 0.9057(11) 0.045(4) Uani 1 1 d . . .
C11 C 0.882(2) 1.020(2) 0.8391(14) 0.058(6) Uani 1 1 d . . .
H11A H 0.8574 1.1140 0.8346 0.070 Uiso 1 1 calc R . .
C12 C 0.927(2) 0.957(3) 0.7800(14) 0.060(6) Uani 1 1 d . . .
H12A H 0.9311 1.0070 0.7352 0.072 Uiso 1 1 calc R . .
C13 C 0.967(2) 0.823(2) 0.7872(12) 0.057(6) Uani 1 1 d . . .
H13A H 0.9986 0.7789 0.7475 0.068 Uiso 1 1 calc R . .
C14 C 0.959(2) 0.750(3) 0.8547(13) 0.063(7) Uani 1 1 d . . .
H14A H 0.9875 0.6575 0.8604 0.076 Uiso 1 1 calc R . .
C15 C 0.7917(17) 0.999(2) 1.1008(10) 0.045(4) Uani 1 1 d . . .
C16 C 0.786(2) 0.922(3) 1.1633(13) 0.059(6) Uani 1 1 d . . .
H16A H 0.7981 0.8247 1.1624 0.071 Uiso 1 1 calc R . .
C17 C 0.762(2) 0.987(3) 1.2294(14) 0.067(7) Uani 1 1 d . . .
H17A H 0.7624 0.9341 1.2735 0.081 Uiso 1 1 calc R . .
C18 C 0.736(2) 1.131(4) 1.2300(13) 0.070(7) Uani 1 1 d . . .
H18A H 0.7170 1.1745 1.2740 0.084 Uiso 1 1 calc R . .
C19 C 0.740(2) 1.212(3) 1.1642(16) 0.064(6) Uani 1 1 d . . .
H19A H 0.7216 1.3080 1.1643 0.077 Uiso 1 1 calc R . .
C20 C 0.7690(18) 1.150(2) 1.1002(11) 0.045(4) Uani 1 1 d . . .
N1 N 0.8309(15) 0.9389(18) 1.0346(10) 0.047(4) Uani 1 1 d . . .
N2 N 0.9110(15) 0.8115(17) 0.9114(9) 0.045(4) Uani 1 1 d . . .
N3 N 0.7777(19) 1.2206(19) 1.0320(11) 0.059(5) Uani 1 1 d . . .
N4 N 0.604(2) 1.048(2) 0.8133(12) 0.069(6) Uani 1 1 d . . .
Cl1 Cl 1.0570(6) 0.6036(6) 1.0950(3) 0.0638(15) Uani 1 1 d . . .
Cl2 Cl 0.7195(7) 0.5706(7) 1.0447(6) 0.094(3) 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
Hg1 N2 2.294(16) . ?
Hg1 Cl2 2.405(8) . ?
Hg1 Cl1 2.405(6) . ?
Hg1 N1 2.442(17) . ?
C1 N4 1.26(4) . ?
C1 C2 1.36(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.38(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.35(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.42(4) . ?
C4 H4A 0.9300 . ?
C5 N4 1.36(3) . ?
C5 C6 1.50(3) . ?
C6 C8 1.54(3) . ?
C6 C7 1.54(3) . ?
C6 H6A 0.9800 . ?
C7 N3 1.40(3) . ?
C7 C9 1.54(2) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 N1 1.25(3) . ?
C9 C10 1.49(3) . ?
C10 N2 1.36(3) . ?
C10 C11 1.39(3) . ?
C11 C12 1.36(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.35(3) . ?
C12 H12A 0.9300 . ?
C13 C14 1.39(3) . ?
C13 H13A 0.9300 . ?
C14 N2 1.34(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.33(3) . ?
C15 N1 1.43(2) . ?
C15 C20 1.44(3) . ?
C16 C17 1.38(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.39(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.40(4) . ?
C18 H18A 0.9300 . ?
C19 C20 1.36(3) . ?
C19 H19A 0.9300 . ?
C20 N3 1.40(3) . ?

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
N2 Hg1 Cl2 122.8(5) . . ?
N2 Hg1 Cl1 118.9(5) . . ?
Cl2 Hg1 Cl1 113.9(3) . . ?
N2 Hg1 N1 71.0(6) . . ?
Cl2 Hg1 N1 100.1(4) . . ?
Cl1 Hg1 N1 120.6(5) . . ?
N4 C1 C2 126(3) . . ?
N4 C1 H1A 116.9 . . ?
C2 C1 H1A 116.9 . . ?
C1 C2 C3 117(3) . . ?
C1 C2 H2A 121.6 . . ?
C3 C2 H2A 121.6 . . ?
C4 C3 C2 119(3) . . ?
C4 C3 H3A 120.4 . . ?
C2 C3 H3A 120.4 . . ?
C3 C4 C5 120(3) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
N4 C5 C4 118(2) . . ?
N4 C5 C6 120(2) . . ?
C4 C5 C6 121(2) . . ?
C5 C6 C8 111.1(19) . . ?
C5 C6 C7 111.4(18) . . ?
C8 C6 C7 110(2) . . ?
C5 C6 H6A 107.9 . . ?
C8 C6 H6A 107.9 . . ?
C7 C6 H6A 107.9 . . ?
N3 C7 C6 112.3(19) . . ?
N3 C7 C9 106.7(17) . . ?
C6 C7 C9 110.8(16) . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 121.5(17) . . ?
N1 C9 C7 119.7(19) . . ?
C10 C9 C7 118.5(16) . . ?
N2 C10 C11 117.7(19) . . ?
N2 C10 C9 116.2(16) . . ?
C11 C10 C9 126.0(19) . . ?
C12 C11 C10 122(2) . . ?
C12 C11 H11A 119.2 . . ?
C10 C11 H11A 119.2 . . ?
C13 C12 C11 119(2) . . ?
C13 C12 H12A 120.3 . . ?
C11 C12 H12A 120.3 . . ?
C12 C13 C14 119(2) . . ?
C12 C13 H13A 120.3 . . ?
C14 C13 H13A 120.3 . . ?
N2 C14 C13 120.3(19) . . ?
N2 C14 H14A 119.8 . . ?
C13 C14 H14A 119.8 . . ?
C16 C15 N1 122(2) . . ?
C16 C15 C20 120.7(19) . . ?
N1 C15 C20 117.3(18) . . ?
C15 C16 C17 121(2) . . ?
C15 C16 H16A 119.7 . . ?
C17 C16 H16A 119.7 . . ?
C16 C17 C18 120(2) . . ?
C16 C17 H17A 120.0 . . ?
C18 C17 H17A 120.0 . . ?
C17 C18 C19 120(2) . . ?
C17 C18 H18A 120.2 . . ?
C19 C18 H18A 120.2 . . ?
C20 C19 C18 120(2) . . ?
C20 C19 H19A 119.8 . . ?
C18 C19 H19A 119.8 . . ?
C19 C20 N3 125(2) . . ?
C19 C20 C15 119(2) . . ?
N3 C20 C15 116.4(17) . . ?
C9 N1 C15 121.4(18) . . ?
C9 N1 Hg1 112.8(13) . . ?
C15 N1 Hg1 125.1(13) . . ?
C14 N2 C10 121.4(18) . . ?
C14 N2 Hg1 121.4(13) . . ?
C10 N2 Hg1 117.1(13) . . ?
C20 N3 C7 117.7(18) . . ?
C1 N4 C5 119(3) . . ?

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         2.473
_refine_diff_density_min         -1.276
_refine_diff_density_rms         0.328
####################################################################### 
# 
# 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_hg5
_database_code_depnum_ccdc_archive 'CCDC 933230'
_audit_update_record             
;
2013-04-10 deposited with the CCDC.
2015-03-23 downloaded from the CCDC.
;
#TrackingRef 'Hg5.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H24 Cl4 Hg2 N4 O2'
_chemical_formula_weight         895.41

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'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   13.266(3)
_cell_length_b                   12.294(3)
_cell_length_c                   16.037(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.24(3)
_cell_angle_gamma                90.00
_cell_volume                     2613.6(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1664
_exptl_absorpt_coefficient_mu    12.167
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3758
_exptl_absorpt_correction_T_max  0.3758
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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 Smart APEX 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            24318
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_sigmaI/netI    0.0821
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5947
_reflns_number_gt                3978
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.0693P)²+2.6509P] 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         5947
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1457
_refine_ls_wR_factor_gt          0.1202
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.004
_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
Hg1 Hg 0.04995(3) 0.24360(4) 0.46394(3) 0.05880(17) Uani 1 1 d . . .
Hg2 Hg 0.52496(3) 0.16811(3) 0.51703(3) 0.04797(15) Uani 1 1 d . . .
O1 O -0.0607(6) 0.2088(9) 0.2839(5) 0.073(3) Uani 1 1 d . . .
O2 O 0.6752(6) 0.3606(8) 0.3619(6) 0.072(2) Uani 1 1 d . . .
N1 N 0.0780(5) 0.1397(7) 0.3437(5) 0.0437(19) Uani 1 1 d . . .
N2 N 0.1995(5) 0.1312(7) 0.4864(5) 0.0390(18) Uani 1 1 d . . .
N3 N 0.3751(5) 0.2619(6) 0.5376(4) 0.0341(17) Uani 1 1 d . . .
N4 N 0.5243(6) 0.3522(7) 0.4322(5) 0.0425(19) Uani 1 1 d . . .
Cl3 Cl -0.0848(3) 0.1547(3) 0.5273(2) 0.0829(10) Uani 1 1 d . . .
C8 C 0.2536(6) 0.1180(8) 0.5673(5) 0.039(2) Uani 1 1 d . . .
H8 H 0.3072 0.0638 0.5618 0.047 Uiso 1 1 calc R . .
C11 C 0.2677(9) 0.1791(10) 0.7463(6) 0.058(3) Uani 1 1 d . . .
H11A H 0.2999 0.1713 0.8013 0.070 Uiso 1 1 calc R . .
H11B H 0.2140 0.2323 0.7496 0.070 Uiso 1 1 calc R . .
C3 C 0.0407(9) 0.0852(10) 0.2043(6) 0.056(3) Uani 1 1 d . . .
H3 H -0.0007 0.0903 0.1563 0.067 Uiso 1 1 calc R . .
C12 C 0.3453(8) 0.2174(9) 0.6837(6) 0.048(2) Uani 1 1 d . . .
H12A H 0.4015 0.1669 0.6848 0.058 Uiso 1 1 calc R . .
H12B H 0.3711 0.2881 0.7010 0.058 Uiso 1 1 calc R . .
C6 C 0.1607(7) 0.0746(9) 0.3462(6) 0.045(2) Uani 1 1 d . . .
C10 C 0.2250(9) 0.0720(10) 0.7175(7) 0.063(3) Uani 1 1 d . . .
H10A H 0.1746 0.0487 0.7560 0.076 Uiso 1 1 calc R . .
H10B H 0.2785 0.0181 0.7190 0.076 Uiso 1 1 calc R . .
C5 C 0.1867(8) 0.0147(9) 0.2791(6) 0.054(3) Uani 1 1 d . . .
H5 H 0.2437 -0.0294 0.2813 0.064 Uiso 1 1 calc R . .
C4 C 0.1248(9) 0.0215(11) 0.2063(7) 0.065(3) Uani 1 1 d . . .
H4 H 0.1412 -0.0176 0.1591 0.079 Uiso 1 1 calc R . .
C1 C -0.1367(9) 0.2166(12) 0.2211(8) 0.071(4) Uani 1 1 d . . .
H1A H -0.1121 0.2569 0.1749 0.107 Uiso 1 1 calc R . .
H1C H -0.1941 0.2533 0.2426 0.107 Uiso 1 1 calc R . .
H1B H -0.1561 0.1450 0.2029 0.107 Uiso 1 1 calc R . .
C2 C 0.0186(8) 0.1422(9) 0.2762(7) 0.053(3) Uani 1 1 d . . .
C7 C 0.2203(7) 0.0712(9) 0.4256(7) 0.047(2) Uani 1 1 d . . .
H7 H 0.2747 0.0237 0.4310 0.056 Uiso 1 1 calc R . .
C9 C 0.1772(8) 0.0760(10) 0.6303(7) 0.060(3) Uani 1 1 d . . .
H9A H 0.1189 0.1238 0.6297 0.072 Uiso 1 1 calc R . .
H9B H 0.1544 0.0039 0.6140 0.072 Uiso 1 1 calc R . .
C13 C 0.3007(7) 0.2259(8) 0.5936(6) 0.042(2) Uani 1 1 d . . .
H13 H 0.2469 0.2805 0.5932 0.050 Uiso 1 1 calc R . .
C14 C 0.3625(7) 0.3525(8) 0.5005(6) 0.041(2) Uani 1 1 d . . .
H14 H 0.3045 0.3916 0.5116 0.050 Uiso 1 1 calc R . .
C15 C 0.4311(6) 0.4001(8) 0.4419(6) 0.037(2) Uani 1 1 d . . .
C16 C 0.4002(8) 0.4901(8) 0.3960(7) 0.051(3) Uani 1 1 d . . .
H16 H 0.3390 0.5233 0.4067 0.061 Uiso 1 1 calc R . .
Cl6 Cl 0.6373(2) 0.2010(3) 0.63154(19) 0.0623(8) Uani 1 1 d . . .
Cl7 Cl 0.1098(3) 0.4245(3) 0.4511(2) 0.0807(10) Uani 1 1 d . . .
Cl8 Cl 0.5039(2) 0.0628(2) 0.39286(18) 0.0630(7) Uani 1 1 d . . .
C19 C 0.5801(8) 0.3952(9) 0.3746(7) 0.050(2) Uani 1 1 d . . .
C20 C 0.7193(10) 0.2802(15) 0.4163(11) 0.100(6) Uani 1 1 d . . .
H20A H 0.7124 0.3023 0.4732 0.149 Uiso 1 1 calc R . .
H20B H 0.7895 0.2724 0.4052 0.149 Uiso 1 1 calc R . .
H20C H 0.6856 0.2119 0.4071 0.149 Uiso 1 1 calc R . .
C17 C 0.4594(9) 0.5313(9) 0.3343(6) 0.055(3) Uani 1 1 d . . .
H17 H 0.4382 0.5902 0.3017 0.066 Uiso 1 1 calc R . .
C18 C 0.5495(9) 0.4826(10) 0.3233(8) 0.061(3) Uani 1 1 d . . .
H18 H 0.5910 0.5071 0.2819 0.073 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
Hg1 N1 2.354(8) . ?
Hg1 Cl3 2.360(4) . ?
Hg1 Cl7 2.373(4) . ?
Hg1 N2 2.433(7) . ?
Hg2 N3 2.333(7) . ?
Hg2 Cl6 2.355(3) . ?
Hg2 Cl8 2.383(3) . ?
Hg2 N4 2.640(8) . ?
O1 C2 1.342(13) . ?
O1 C1 1.400(12) . ?
O2 C19 1.355(12) . ?
O2 C20 1.428(15) . ?
N1 C2 1.315(12) . ?
N1 C6 1.358(12) . ?
N2 C7 1.262(13) . ?
N2 C8 1.466(11) . ?
N3 C14 1.270(11) . ?
N3 C13 1.430(12) . ?
N4 C19 1.317(13) . ?
N4 C15 1.384(11) . ?
C8 C13 1.520(13) . ?
C8 C9 1.548(14) . ?
C8 H8 0.9800 . ?
C11 C10 1.499(16) . ?
C11 C12 1.539(15) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C3 C4 1.362(16) . ?
C3 C2 1.390(16) . ?
C3 H3 0.9300 . ?
C12 C13 1.543(12) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C6 C5 1.360(14) . ?
C6 C7 1.472(13) . ?
C10 C9 1.513(14) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C5 C4 1.404(14) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H1B 0.9600 . ?
C7 H7 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C13 H13 0.9800 . ?
C14 C15 1.455(13) . ?
C14 H14 0.9300 . ?
C15 C16 1.384(13) . ?
C16 C17 1.383(15) . ?
C16 H16 0.9300 . ?
C19 C18 1.403(15) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C17 C18 1.354(16) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Hg1 Cl3 104.4(2) . . ?
N1 Hg1 Cl7 111.9(2) . . ?
Cl3 Hg1 Cl7 137.15(13) . . ?
N1 Hg1 N2 70.1(3) . . ?
Cl3 Hg1 N2 107.5(2) . . ?
Cl7 Hg1 N2 105.8(2) . . ?
N3 Hg2 Cl6 108.76(19) . . ?
N3 Hg2 Cl8 108.3(2) . . ?
Cl6 Hg2 Cl8 142.69(11) . . ?
N3 Hg2 N4 70.3(2) . . ?
Cl6 Hg2 N4 104.11(19) . . ?
Cl8 Hg2 N4 92.1(2) . . ?
C2 O1 C1 121.4(10) . . ?
C19 O2 C20 119.2(9) . . ?
C2 N1 C6 119.7(9) . . ?
C2 N1 Hg1 123.6(7) . . ?
C6 N1 Hg1 116.7(6) . . ?
C7 N2 C8 120.3(8) . . ?
C7 N2 Hg1 114.7(6) . . ?
C8 N2 Hg1 124.2(6) . . ?
C14 N3 C13 118.9(8) . . ?
C14 N3 Hg2 117.7(6) . . ?
C13 N3 Hg2 123.3(6) . . ?
C19 N4 C15 115.9(8) . . ?
C19 N4 Hg2 135.7(7) . . ?
C15 N4 Hg2 106.9(5) . . ?
N2 C8 C13 109.3(8) . . ?
N2 C8 C9 107.7(7) . . ?
C13 C8 C9 112.4(8) . . ?
N2 C8 H8 109.1 . . ?
C13 C8 H8 109.1 . . ?
C9 C8 H8 109.1 . . ?
C10 C11 C12 108.9(9) . . ?
C10 C11 H11A 109.9 . . ?
C12 C11 H11A 109.9 . . ?
C10 C11 H11B 109.9 . . ?
C12 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
C4 C3 C2 118.0(9) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C11 C12 C13 112.9(8) . . ?
C11 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
N1 C6 C5 121.7(9) . . ?
N1 C6 C7 116.6(9) . . ?
C5 C6 C7 121.7(9) . . ?
C11 C10 C9 113.2(10) . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C6 C5 C4 117.9(10) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C3 C4 C5 120.4(10) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1C C1 H1B 109.5 . . ?
N1 C2 O1 112.6(10) . . ?
N1 C2 C3 122.1(10) . . ?
O1 C2 C3 125.1(9) . . ?
N2 C7 C6 121.7(9) . . ?
N2 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C10 C9 C8 110.7(8) . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
N3 C13 C8 112.5(8) . . ?
N3 C13 C12 111.1(8) . . ?
C8 C13 C12 109.8(8) . . ?
N3 C13 H13 107.7 . . ?
C8 C13 H13 107.7 . . ?
C12 C13 H13 107.7 . . ?
N3 C14 C15 125.5(9) . . ?
N3 C14 H14 117.3 . . ?
C15 C14 H14 117.3 . . ?
C16 C15 N4 121.9(9) . . ?
C16 C15 C14 119.0(9) . . ?
N4 C15 C14 119.1(8) . . ?
C17 C16 C15 120.6(10) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
N4 C19 O2 122.1(10) . . ?
N4 C19 C18 124.1(10) . . ?
O2 C19 C18 113.7(10) . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C17 C16 117.4(10) . . ?
C18 C17 H17 121.3 . . ?
C16 C17 H17 121.3 . . ?
C17 C18 C19 120.0(11) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.059
_refine_diff_density_min         -2.313
_refine_diff_density_rms         0.218
####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 933231'
_audit_update_record             
;
2013-04-10 deposited with the CCDC.
2015-03-23 downloaded from the CCDC.
;
#TrackingRef 'Hg6.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 Cl4 Hg2 N4 O2'
_chemical_formula_weight         869.38

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'
Hg Hg -2.3894 9.2266 '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                   7.8745(8)
_cell_length_b                   9.5915(10)
_cell_length_c                   17.3499(18)
_cell_angle_alpha                100.8390(10)
_cell_angle_beta                 91.4490(10)
_cell_angle_gamma                106.9250(10)
_cell_volume                     1226.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9357
_cell_measurement_theta_min      1.20
_cell_measurement_theta_max      26.86

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             804
_exptl_absorpt_coefficient_mu    12.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1057
_exptl_absorpt_correction_T_max  0.1708
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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 P4'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9357
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.20
_diffrn_reflns_theta_max         26.86
_reflns_number_total             4680
_reflns_number_gt                2068
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.0385P)²+0.0000P] 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         4680
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0850
_refine_ls_wR_factor_gt          0.0676
_refine_ls_goodness_of_fit_ref   0.868
_refine_ls_restrained_S_all      0.868
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Hg1 Hg 0.86710(12) 0.12905(10) 0.17235(5) 0.0475(3) Uani 1 1 d . . .
Hg2 Hg 1.63228(12) -0.12936(10) 0.32755(5) 0.0475(3) Uani 1 1 d . . .
C1 C 1.124(3) 0.470(2) 0.1024(14) 0.053(6) Uani 1 1 d . . .
C2 C 1.203(3) 0.527(2) 0.0405(13) 0.054(7) Uani 1 1 d . . .
H2A H 1.2033 0.6210 0.0334 0.065 Uiso 1 1 calc R . .
C3 C 1.279(3) 0.445(2) -0.0086(13) 0.060(7) Uani 1 1 d . . .
H3A H 1.3304 0.4790 -0.0518 0.072 Uiso 1 1 calc R . .
C4 C 1.280(3) 0.306(2) 0.0051(13) 0.059(7) Uani 1 1 d . . .
H4A H 1.3339 0.2471 -0.0282 0.071 Uiso 1 1 calc R . .
C5 C 1.199(2) 0.258(2) 0.0690(11) 0.033(5) Uani 1 1 d . . .
C6 C 1.199(2) 0.1093(16) 0.0834(10) 0.035(5) Uani 1 1 d . . .
H6A H 1.2804 0.0646 0.0601 0.042 Uiso 1 1 calc R . .
C7 C 1.121(3) -0.0878(19) 0.1490(12) 0.045(6) Uani 1 1 d . . .
H7A H 1.2184 -0.1100 0.1211 0.054 Uiso 1 1 calc R . .
H7B H 1.0155 -0.1727 0.1329 0.054 Uiso 1 1 calc R . .
C8 C 1.166(2) -0.065(2) 0.2365(11) 0.056(6) Uani 1 1 d . . .
H8A H 1.1832 -0.1556 0.2482 0.068 Uiso 1 1 calc R . .
H8B H 1.0672 -0.0468 0.2643 0.068 Uiso 1 1 calc R . .
C9 C 1.335(2) 0.0648(15) 0.2659(10) 0.048(5) Uani 1 1 d . . .
H9A H 1.4332 0.0446 0.2384 0.057 Uiso 1 1 calc R . .
H9B H 1.3180 0.1539 0.2523 0.057 Uiso 1 1 calc R . .
C10 C 1.384(3) 0.096(2) 0.3536(11) 0.053(6) Uani 1 1 d . . .
H10A H 1.2914 0.1238 0.3825 0.063 Uiso 1 1 calc R . .
H10B H 1.4946 0.1762 0.3677 0.063 Uiso 1 1 calc R . .
C11 C 1.303(2) -0.119(2) 0.4169(10) 0.048(6) Uani 1 1 d . . .
H11A H 1.2199 -0.0775 0.4410 0.057 Uiso 1 1 calc R . .
C12 C 1.305(3) -0.262(2) 0.4319(13) 0.039(5) Uani 1 1 d . . .
C13 C 1.219(2) -0.305(2) 0.4943(11) 0.047(6) Uani 1 1 d . . .
H13A H 1.1623 -0.2455 0.5254 0.057 Uiso 1 1 calc R . .
C14 C 1.219(2) -0.442(3) 0.5100(12) 0.058(7) Uani 1 1 d . . .
H14A H 1.1677 -0.4740 0.5539 0.069 Uiso 1 1 calc R . .
C15 C 1.294(3) -0.528(3) 0.4602(14) 0.056(7) Uani 1 1 d . . .
H15A H 1.2939 -0.6206 0.4691 0.067 Uiso 1 1 calc R . .
C16 C 1.374(2) -0.476(2) 0.3943(12) 0.041(5) Uani 1 1 d . . .
C17 C 0.981(3) 0.523(2) 0.2219(14) 0.074(8) Uani 1 1 d . . .
H17A H 0.9386 0.6015 0.2495 0.112 Uiso 1 1 calc R . .
H17B H 1.0697 0.5076 0.2553 0.112 Uiso 1 1 calc R . .
H17C H 0.8833 0.4332 0.2075 0.112 Uiso 1 1 calc R . .
C18 C 1.519(3) -0.516(2) 0.2778(15) 0.090(10) Uani 1 1 d . . .
H18A H 1.5655 -0.5887 0.2476 0.136 Uiso 1 1 calc R . .
H18B H 1.6132 -0.4239 0.2946 0.136 Uiso 1 1 calc R . .
H18C H 1.4280 -0.4994 0.2459 0.136 Uiso 1 1 calc R . .
N1 N 1.116(2) 0.3385(17) 0.1181(9) 0.037(4) Uani 1 1 d . . .
N2 N 1.089(2) 0.0427(19) 0.1269(9) 0.045(5) Uani 1 1 d . . .
N3 N 1.4057(18) -0.0463(16) 0.3731(9) 0.033(4) Uani 1 1 d . . .
N4 N 1.3832(19) -0.3423(17) 0.3808(9) 0.037(4) Uani 1 1 d . . .
Cl1 Cl 0.8660(9) 0.1883(7) 0.3135(4) 0.074(2) Uani 1 1 d . . .
Cl2 Cl 0.6595(8) 0.1575(8) 0.0786(4) 0.072(2) Uani 1 1 d . . .
Cl3 Cl 1.8395(8) -0.1576(8) 0.4211(4) 0.078(2) Uani 1 1 d . . .
Cl4 Cl 1.6321(9) -0.1883(7) 0.1864(4) 0.075(2) Uani 1 1 d . . .
O2 O 1.057(2) 0.5640(16) 0.1527(10) 0.064(5) Uani 1 1 d . . .
O1 O 1.444(2) -0.5679(16) 0.3459(11) 0.072(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
Hg1 N2 2.246(16) . ?
Hg1 Cl2 2.385(6) . ?
Hg1 Cl1 2.408(6) . ?
Hg1 N1 2.697(15) . ?
Hg2 N3 2.259(14) . ?
Hg2 Cl3 2.379(7) . ?
Hg2 Cl4 2.407(6) . ?
C1 N1 1.33(2) . ?
C1 O2 1.36(2) . ?
C1 C2 1.38(3) . ?
C2 C3 1.32(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.40(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.38(3) . ?
C4 H4A 0.9300 . ?
C5 N1 1.35(2) . ?
C5 C6 1.49(2) . ?
C6 N2 1.27(2) . ?
C6 H6A 0.9300 . ?
C7 N2 1.46(2) . ?
C7 C8 1.51(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.529(12) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.51(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N3 1.52(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N3 1.27(2) . ?
C11 C12 1.44(3) . ?
C11 H11A 0.9300 . ?
C12 N4 1.35(2) . ?
C12 C13 1.36(3) . ?
C13 C14 1.39(3) . ?
C13 H13A 0.9300 . ?
C14 C15 1.35(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.42(3) . ?
C15 H15A 0.9300 . ?
C16 N4 1.33(2) . ?
C16 O1 1.35(2) . ?
C17 O2 1.42(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 O1 1.44(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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
N2 Hg1 Cl2 118.0(5) . . ?
N2 Hg1 Cl1 115.8(5) . . ?
Cl2 Hg1 Cl1 126.2(2) . . ?
N2 Hg1 N1 68.8(5) . . ?
Cl2 Hg1 N1 86.6(4) . . ?
Cl1 Hg1 N1 112.1(4) . . ?
N3 Hg2 Cl3 118.0(4) . . ?
N3 Hg2 Cl4 115.4(4) . . ?
Cl3 Hg2 Cl4 126.5(2) . . ?
N1 C1 O2 119(2) . . ?
N1 C1 C2 126(2) . . ?
O2 C1 C2 114.9(19) . . ?
C3 C2 C1 118(2) . . ?
C3 C2 H2A 120.9 . . ?
C1 C2 H2A 120.9 . . ?
C2 C3 C4 119.4(19) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C5 C4 C3 118.7(19) . . ?
C5 C4 H4A 120.6 . . ?
C3 C4 H4A 120.6 . . ?
N1 C5 C4 122.7(19) . . ?
N1 C5 C6 118.4(16) . . ?
C4 C5 C6 118.8(17) . . ?
N2 C6 C5 121.1(16) . . ?
N2 C6 H6A 119.4 . . ?
C5 C6 H6A 119.4 . . ?
N2 C7 C8 112.5(15) . . ?
N2 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
N2 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 C9 112.1(12) . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C8 114.7(11) . . ?
C10 C9 H9A 108.6 . . ?
C8 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C8 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C9 C10 N3 107.3(15) . . ?
C9 C10 H10A 110.3 . . ?
N3 C10 H10A 110.3 . . ?
C9 C10 H10B 110.3 . . ?
N3 C10 H10B 110.3 . . ?
H10A C10 H10B 108.5 . . ?
N3 C11 C12 125.0(17) . . ?
N3 C11 H11A 117.5 . . ?
C12 C11 H11A 117.5 . . ?
N4 C12 C13 125.9(19) . . ?
N4 C12 C11 117.4(18) . . ?
C13 C12 C11 116.6(19) . . ?
C12 C13 C14 118(2) . . ?
C12 C13 H13A 121.1 . . ?
C14 C13 H13A 121.1 . . ?
C15 C14 C13 118.4(19) . . ?
C15 C14 H14A 120.8 . . ?
C13 C14 H14A 120.8 . . ?
C14 C15 C16 120(2) . . ?
C14 C15 H15A 120.1 . . ?
C16 C15 H15A 120.1 . . ?
N4 C16 O1 120.5(17) . . ?
N4 C16 C15 122.3(19) . . ?
O1 C16 C15 117.2(18) . . ?
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 . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1 N1 C5 115.1(18) . . ?
C1 N1 Hg1 134.2(14) . . ?
C5 N1 Hg1 103.3(12) . . ?
C6 N2 C7 116.7(16) . . ?
C6 N2 Hg1 121.4(12) . . ?
C7 N2 Hg1 121.9(13) . . ?
C11 N3 C10 122.2(16) . . ?
C11 N3 Hg2 118.1(12) . . ?
C10 N3 Hg2 119.8(12) . . ?
C16 N4 C12 115.5(17) . . ?
C1 O2 C17 121.0(16) . . ?
C16 O1 C18 116.3(16) . . ?

_diffrn_measured_fraction_theta_max 0.889
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.540
_refine_diff_density_min         -1.164
_refine_diff_density_rms         0.145
####################################################################### 
# 
# 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_cs6
_database_code_depnum_ccdc_archive 'CCDC 933232'
_audit_update_record             
;
2013-04-10 deposited with the CCDC.
2015-03-23 downloaded from the CCDC.
;
#TrackingRef 'L6.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H11 N2 O'
_chemical_formula_weight         163.20

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'

_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                   5.4024(8)
_cell_length_b                   14.0910(16)
_cell_length_c                   11.7517(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.611(12)
_cell_angle_gamma                90.00
_cell_volume                     873.02(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3777
_cell_measurement_theta_min      3.39
_cell_measurement_theta_max      29.22

_exptl_crystal_description       block
_exptl_crystal_colour            coloerless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9641
_exptl_absorpt_correction_T_max  0.9826
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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 II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3777
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_sigmaI/netI    0.1199
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.39
_diffrn_reflns_theta_max         29.22
_reflns_number_total             1970
_reflns_number_gt                812
_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    SHELXP-97
_computing_publication_material  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)+(0.0384P)²+0.0000P] 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         1970
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1789
_refine_ls_R_factor_gt           0.0628
_refine_ls_wR_factor_ref         0.1393
_refine_ls_wR_factor_gt          0.1041
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_restrained_S_all      0.920
_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
N2 N 0.1489(4) 0.73962(14) 0.79112(17) 0.0459(6) Uani 1 1 d . . .
O1 O -0.1552(4) 0.82499(14) 0.85757(15) 0.0682(6) Uani 1 1 d . . .
N1 N 0.5953(4) 0.58289(15) 0.71092(17) 0.0491(6) Uani 1 1 d . . .
C4 C 0.3161(5) 0.66678(18) 0.8092(2) 0.0440(7) Uani 1 1 d . . .
C3 C 0.4554(5) 0.6534(2) 0.7162(2) 0.0473(7) Uani 1 1 d . . .
H3A H 0.4395 0.6994 0.6582 0.057 Uiso 1 1 calc R . .
C8 C 0.0170(6) 0.75377(19) 0.8713(2) 0.0496(7) Uani 1 1 d . . .
C5 C 0.3510(6) 0.60965(18) 0.9058(2) 0.0544(8) Uani 1 1 d . . .
H5A H 0.4668 0.5599 0.9151 0.065 Uiso 1 1 calc R . .
C7 C 0.0425(6) 0.7001(2) 0.9724(2) 0.0624(9) Uani 1 1 d . . .
H7A H -0.0532 0.7135 1.0273 0.075 Uiso 1 1 calc R . .
C6 C 0.2123(7) 0.6270(2) 0.9887(2) 0.0653(9) Uani 1 1 d . . .
H6A H 0.2339 0.5893 1.0551 0.078 Uiso 1 1 calc R . .
C9 C -0.1890(7) 0.8807(2) 0.7537(2) 0.0726(10) Uani 1 1 d . . .
H9A H -0.3154 0.9285 0.7547 0.109 Uiso 1 1 calc R . .
H9B H -0.2429 0.8406 0.6870 0.109 Uiso 1 1 calc R . .
H9C H -0.0314 0.9107 0.7498 0.109 Uiso 1 1 calc R . .
C2 C 0.7228(5) 0.57903(19) 0.6137(2) 0.0543(8) Uani 1 1 d . . .
H2A H 0.9045 0.5746 0.6438 0.065 Uiso 1 1 calc R . .
H2B H 0.6891 0.6371 0.5687 0.065 Uiso 1 1 calc R . .
C1 C 0.6347(5) 0.49503(18) 0.53499(19) 0.0489(7) Uani 1 1 d . . .
H1A H 0.7473 0.4873 0.4817 0.059 Uiso 1 1 calc R . .
H1B H 0.6466 0.4381 0.5823 0.059 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
N2 C8 1.314(3) . ?
N2 C4 1.353(3) . ?
O1 C8 1.354(3) . ?
O1 C9 1.429(3) . ?
N1 C3 1.258(3) . ?
N1 C2 1.458(3) . ?
C4 C5 1.371(3) . ?
C4 C3 1.468(4) . ?
C3 H3A 0.9300 . ?
C8 C7 1.390(4) . ?
C5 C6 1.374(4) . ?
C5 H5A 0.9300 . ?
C7 C6 1.365(4) . ?
C7 H7A 0.9300 . ?
C6 H6A 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C2 C1 1.514(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C1 C1 1.513(5) 3_666 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?

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
C8 N2 C4 116.8(2) . . ?
C8 O1 C9 117.7(2) . . ?
C3 N1 C2 117.4(2) . . ?
N2 C4 C5 122.8(3) . . ?
N2 C4 C3 114.4(2) . . ?
C5 C4 C3 122.8(3) . . ?
N1 C3 C4 123.3(3) . . ?
N1 C3 H3A 118.4 . . ?
C4 C3 H3A 118.4 . . ?
N2 C8 O1 119.6(2) . . ?
N2 C8 C7 124.2(3) . . ?
O1 C8 C7 116.3(3) . . ?
C4 C5 C6 119.0(3) . . ?
C4 C5 H5A 120.5 . . ?
C6 C5 H5A 120.5 . . ?
C6 C7 C8 118.0(3) . . ?
C6 C7 H7A 121.0 . . ?
C8 C7 H7A 121.0 . . ?
C7 C6 C5 119.2(3) . . ?
C7 C6 H6A 120.4 . . ?
C5 C6 H6A 120.4 . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C2 C1 111.6(2) . . ?
N1 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C1 C1 C2 113.4(3) 3_666 . ?
C1 C1 H1A 108.9 3_666 . ?
C2 C1 H1A 108.9 . . ?
C1 C1 H1B 108.9 3_666 . ?
C2 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?

_diffrn_measured_fraction_theta_max 0.830
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 933233'
_audit_update_record             
;
2013-04-10 deposited with the CCDC.
2015-03-23 downloaded from the CCDC.
;
#TrackingRef 'Zn1.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 Cl2 N4 O0 Zn'
_chemical_formula_weight         450.65

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                   13.404(3)
_cell_length_b                   15.715(3)
_cell_length_c                   19.102(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4023.7(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    34025
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      27.47

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1840
_exptl_absorpt_coefficient_mu    1.498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5891
_exptl_absorpt_correction_T_max  0.7649
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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 P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            34025
_diffrn_reflns_av_R_equivalents  0.0810
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         27.47
_reflns_number_total             4586
_reflns_number_gt                2918
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.1294P)²+19.0179P] 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         4586
_refine_ls_number_parameters     244
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0662
_refine_ls_wR_factor_ref         0.2155
_refine_ls_wR_factor_gt          0.1811
_refine_ls_goodness_of_fit_ref   0.846
_refine_ls_restrained_S_all      0.850
_refine_ls_shift/su_max          2.317
_refine_ls_shift/su_mean         0.086

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 0.52250(4) 0.20544(4) 0.56349(3) 0.0398(2) Uani 1 1 d . . .
C1 C 0.3747(4) 0.1815(4) 0.4436(3) 0.0495(14) Uani 1 1 d . . .
H1A H 0.3368 0.2235 0.4653 0.059 Uiso 1 1 calc R . .
C2 C 0.3403(4) 0.1457(4) 0.3823(3) 0.0537(15) Uani 1 1 d . . .
H2A H 0.2806 0.1638 0.3625 0.064 Uiso 1 1 calc R . .
C3 C 0.3957(4) 0.0833(4) 0.3511(3) 0.0511(15) Uani 1 1 d . . .
H3A H 0.3739 0.0580 0.3098 0.061 Uiso 1 1 calc R . .
C4 C 0.4844(4) 0.0580(4) 0.3815(3) 0.0448(13) Uani 1 1 d . . .
H4A H 0.5225 0.0152 0.3610 0.054 Uiso 1 1 calc R . .
C5 C 0.5157(4) 0.0963(3) 0.4419(3) 0.0339(10) Uani 1 1 d . . .
C6 C 0.6116(4) 0.0765(3) 0.4783(3) 0.0343(10) Uani 1 1 d . . .
C7 C 0.6829(4) 0.0123(3) 0.4500(3) 0.0382(11) Uani 1 1 d . . .
H7A H 0.7398 0.0082 0.4803 0.057 Uiso 1 1 d R . .
H7B H 0.6506 -0.0421 0.4471 0.057 Uiso 1 1 d R . .
H7C H 0.7043 0.0296 0.4041 0.057 Uiso 1 1 d R . .
C8 C 0.7225(4) 0.1097(3) 0.5713(3) 0.0370(11) Uani 1 1 d . . .
C9 C 0.7172(4) 0.1170(4) 0.6444(3) 0.0488(14) Uani 1 1 d . . .
H9A H 0.6555 0.1237 0.6660 0.059 Uiso 1 1 calc R . .
C10 C 0.8021(5) 0.1142(5) 0.6842(3) 0.0602(17) Uani 1 1 d . . .
H10A H 0.7982 0.1193 0.7326 0.072 Uiso 1 1 calc R . .
C11 C 0.8938(5) 0.1038(5) 0.6519(3) 0.0567(16) Uani 1 1 d . . .
H11A H 0.9515 0.1006 0.6787 0.068 Uiso 1 1 calc R . .
C12 C 0.8995(4) 0.0981(4) 0.5802(3) 0.0503(15) Uani 1 1 d . . .
H12A H 0.9618 0.0922 0.5592 0.060 Uiso 1 1 calc R . .
C13 C 0.8142(4) 0.1008(3) 0.5379(3) 0.0382(11) Uani 1 1 d . . .
C14 C 0.7713(4) 0.0635(4) 0.4111(3) 0.0478(15) Uani 1 1 d D . .
C15 C 0.8420(5) -0.0125(5) 0.3835(4) 0.068(2) Uani 1 1 d . . .
H15A H 0.8979 0.0110 0.3588 0.102 Uiso 1 1 calc R . .
H15B H 0.8047 -0.0487 0.3526 0.102 Uiso 1 1 calc R . .
H15C H 0.8654 -0.0452 0.4226 0.102 Uiso 1 1 calc R . .
C16 C 0.7290(4) 0.1103(4) 0.3547(3) 0.0397(12) Uani 1 1 d . . .
C17 C 0.7152(5) 0.1846(4) 0.3671(4) 0.077(2) Uani 1 1 d D . .
H17A H 0.7397 0.2089 0.4081 0.092 Uiso 1 1 calc R . .
C18 C 0.6560(6) 0.2388(5) 0.3138(4) 0.075(2) Uani 1 1 d . . .
H18A H 0.6430 0.2963 0.3209 0.090 Uiso 1 1 calc R . .
C19 C 0.6240(6) 0.1964(5) 0.2555(4) 0.075(2) Uani 1 1 d . . .
H19A H 0.5863 0.2234 0.2212 0.090 Uiso 1 1 calc R . .
C20 C 0.6496(5) 0.1133(5) 0.2498(3) 0.0655(19) Uani 1 1 d . . .
H20A H 0.6306 0.0846 0.2093 0.079 Uiso 1 1 calc R . .
N1 N 0.8271(3) 0.1074(3) 0.4653(2) 0.0468(12) Uani 1 1 d . . .
N2 N 0.6306(3) 0.1182(3) 0.5352(2) 0.0343(9) Uani 1 1 d . . .
N3 N 0.4607(3) 0.1577(3) 0.4725(2) 0.0397(10) Uani 1 1 d . . .
N4 N 0.7000(4) 0.0697(4) 0.2980(2) 0.0537(13) Uani 1 1 d . . .
Cl1 Cl 0.43460(12) 0.16796(11) 0.65566(9) 0.0582(4) Uani 1 1 d . . .
Cl2 Cl 0.58078(12) 0.33650(10) 0.55665(9) 0.0589(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 N3 2.066(5) . ?
Zn1 N2 2.067(4) . ?
Zn1 Cl1 2.1990(17) . ?
Zn1 Cl2 2.2066(17) . ?
C1 N3 1.332(7) . ?
C1 C2 1.378(9) . ?
C1 H1A 0.9300 . ?
C2 C3 1.367(9) . ?
C2 H2A 0.9300 . ?
C3 C4 1.382(8) . ?
C3 H3A 0.9300 . ?
C4 C5 1.368(7) . ?
C4 H4A 0.9300 . ?
C5 N3 1.349(7) . ?
C5 C6 1.494(7) . ?
C6 N2 1.296(7) . ?
C6 C7 1.490(7) . ?
C7 C14 1.613(8) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C13 1.392(7) . ?
C8 N2 1.417(6) . ?
C8 C9 1.404(7) . ?
C9 C10 1.368(8) . ?
C9 H9A 0.9300 . ?
C10 C11 1.385(9) . ?
C10 H10A 0.9300 . ?
C11 C12 1.375(9) . ?
C11 H11A 0.9300 . ?
C12 C13 1.401(8) . ?
C12 H12A 0.9300 . ?
C13 N1 1.402(7) . ?
C14 C16 1.423(8) . ?
C14 N1 1.452(8) . ?
C14 C15 1.613(8) . ?
C14 H7C 1.0531 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.206(8) . ?
C16 N4 1.316(7) . ?
C17 C18 1.547(9) . ?
C17 H17A 0.9300 . ?
C18 C19 1.366(11) . ?
C18 H18A 0.9300 . ?
C19 C20 1.355(11) . ?
C19 H19A 0.9300 . ?
C20 N4 1.332(8) . ?
C20 H20A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Zn1 N2 79.68(17) . . ?
N3 Zn1 Cl1 111.19(14) . . ?
N2 Zn1 Cl1 114.04(13) . . ?
N3 Zn1 Cl2 115.53(14) . . ?
N2 Zn1 Cl2 110.81(13) . . ?
Cl1 Zn1 Cl2 119.15(7) . . ?
N3 C1 C2 121.8(6) . . ?
N3 C1 H1A 119.1 . . ?
C2 C1 H1A 119.1 . . ?
C3 C2 C1 118.8(6) . . ?
C3 C2 H2A 120.6 . . ?
C1 C2 H2A 120.6 . . ?
C2 C3 C4 119.4(6) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C5 C4 C3 119.5(6) . . ?
C5 C4 H4A 120.3 . . ?
C3 C4 H4A 120.3 . . ?
N3 C5 C4 120.9(5) . . ?
N3 C5 C6 114.7(4) . . ?
C4 C5 C6 124.4(5) . . ?
N2 C6 C7 121.4(4) . . ?
N2 C6 C5 117.0(5) . . ?
C7 C6 C5 121.6(5) . . ?
C6 C7 C14 107.5(4) . . ?
C6 C7 H7A 109.6 . . ?
C14 C7 H7A 74.2 . . ?
C6 C7 H7B 109.5 . . ?
C14 C7 H7B 138.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.3 . . ?
C14 C7 H7C 38.8 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 N2 123.6(5) . . ?
C13 C8 C9 120.6(5) . . ?
N2 C8 C9 115.6(5) . . ?
C10 C9 C8 120.5(6) . . ?
C10 C9 H9A 119.7 . . ?
C8 C9 H9A 119.7 . . ?
C9 C10 C11 119.6(6) . . ?
C9 C10 H10A 120.2 . . ?
C11 C10 H10A 120.2 . . ?
C12 C11 C10 120.1(6) . . ?
C12 C11 H11A 120.0 . . ?
C10 C11 H11A 119.9 . . ?
C11 C12 C13 121.8(6) . . ?
C11 C12 H12A 119.1 . . ?
C13 C12 H12A 119.1 . . ?
C8 C13 C12 117.4(5) . . ?
C8 C13 N1 123.7(5) . . ?
C12 C13 N1 118.1(5) . . ?
C16 C14 N1 119.9(5) . . ?
C16 C14 C7 108.2(4) . . ?
N1 C14 C7 106.7(4) . . ?
C16 C14 C15 111.7(5) . . ?
N1 C14 C15 106.5(5) . . ?
C7 C14 C15 102.3(5) . . ?
C16 C14 H7C 79.9 . . ?
N1 C14 H7C 140.4 . . ?
C7 C14 H7C 34.8 . . ?
C15 C14 H7C 94.9 . . ?
C14 C15 H15A 109.8 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.2 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 N4 125.9(6) . . ?
C17 C16 C14 114.4(6) . . ?
N4 C16 C14 119.4(5) . . ?
C16 C17 C18 118.8(7) . . ?
C16 C17 H17A 120.8 . . ?
C18 C17 H17A 120.3 . . ?
C19 C18 C17 115.4(7) . . ?
C19 C18 H18A 122.0 . . ?
C17 C18 H18A 122.6 . . ?
C20 C19 C18 117.1(7) . . ?
C20 C19 H19A 121.4 . . ?
C18 C19 H19A 121.5 . . ?
N4 C20 C19 124.7(7) . . ?
N4 C20 H20A 117.6 . . ?
C19 C20 H20A 117.7 . . ?
C13 N1 C14 127.3(5) . . ?
C6 N2 C8 122.1(4) . . ?
C6 N2 Zn1 114.7(3) . . ?
C8 N2 Zn1 123.0(3) . . ?
C1 N3 C5 119.7(5) . . ?
C1 N3 Zn1 126.4(4) . . ?
C5 N3 Zn1 113.9(3) . . ?
C16 N4 C20 118.0(6) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.890
_refine_diff_density_min         -1.558
_refine_diff_density_rms         0.096
####################################################################### 
# 
# 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_1c
_database_code_depnum_ccdc_archive 'CCDC 933234'
_audit_update_record             
;
2013-04-10 deposited with the CCDC.
2015-03-23 downloaded from the CCDC.
;
#TrackingRef 'Zn2.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H21 Cl2 N4 O0 Zn'
_chemical_formula_weight         465.69

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                   10.180(2)
_cell_length_b                   13.936(3)
_cell_length_c                   14.518(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.28(3)
_cell_angle_gamma                90.00
_cell_volume                     2059.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    18456
_cell_measurement_theta_min      3.16
_cell_measurement_theta_max      27.48

_exptl_crystal_description       bolck
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             956
_exptl_absorpt_coefficient_mu    1.466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6649
_exptl_absorpt_correction_T_max  0.8100
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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 P4'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            18456
_diffrn_reflns_av_R_equivalents  0.1587
_diffrn_reflns_av_sigmaI/netI    0.1403
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4676
_reflns_number_gt                2220
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.0928P)²+6.6131P] 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         4676
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2347
_refine_ls_R_factor_gt           0.1329
_refine_ls_wR_factor_ref         0.2914
_refine_ls_wR_factor_gt          0.2445
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.52830(13) 0.70022(8) 0.02443(7) 0.0580(4) Uani 1 1 d . . .
C1 C 0.3123(12) 0.6932(7) -0.1272(7) 0.066(3) Uani 1 1 d . . .
H1A H 0.3716 0.7233 -0.1656 0.079 Uiso 1 1 calc R . .
C2 C 0.1894(13) 0.6723(8) -0.1608(7) 0.074(3) Uani 1 1 d . . .
H2A H 0.1648 0.6885 -0.2209 0.088 Uiso 1 1 calc R . .
C3 C 0.1040(14) 0.6275(9) -0.1051(8) 0.086(4) Uani 1 1 d . . .
H3A H 0.0195 0.6131 -0.1264 0.103 Uiso 1 1 calc R . .
C4 C 0.1429(12) 0.6034(8) -0.0166(7) 0.071(3) Uani 1 1 d . . .
H4A H 0.0847 0.5723 0.0218 0.085 Uiso 1 1 calc R . .
C5 C 0.2649(11) 0.6247(6) 0.0144(6) 0.053(3) Uani 1 1 d . . .
C6 C 0.3206(12) 0.5997(6) 0.1077(6) 0.054(3) Uani 1 1 d . . .
C7 C 0.4999(11) 0.6018(7) 0.2118(6) 0.056(3) Uani 1 1 d . . .
C8 C 0.6270(12) 0.5674(8) 0.2141(8) 0.073(3) Uani 1 1 d . . .
H8A H 0.6668 0.5514 0.1592 0.087 Uiso 1 1 calc R . .
C9 C 0.6962(14) 0.5562(8) 0.2960(8) 0.079(3) Uani 1 1 d . . .
H9A H 0.7808 0.5310 0.2972 0.095 Uiso 1 1 calc R . .
C10 C 0.6373(14) 0.5829(8) 0.3751(8) 0.073(3) Uani 1 1 d . . .
C11 C 0.5105(13) 0.6179(8) 0.3749(7) 0.069(3) Uani 1 1 d . . .
H11A H 0.4731 0.6344 0.4306 0.082 Uiso 1 1 calc R . .
C12 C 0.4360(11) 0.6292(7) 0.2924(7) 0.059(3) Uani 1 1 d . . .
C13 C 0.7130(15) 0.5695(11) 0.4653(9) 0.106(5) Uani 1 1 d . . .
H13A H 0.7991 0.5452 0.4531 0.159 Uiso 1 1 calc R . .
H13B H 0.6673 0.5248 0.5033 0.159 Uiso 1 1 calc R . .
H13C H 0.7205 0.6300 0.4965 0.159 Uiso 1 1 calc R . .
C14 C 0.2356(11) 0.5517(7) 0.1767(6) 0.060(3) Uani 1 1 d . . .
H14A H 0.2853 0.5412 0.2328 0.090 Uiso 1 1 calc R . .
H14B H 0.2056 0.4912 0.1526 0.090 Uiso 1 1 calc R . .
H14C H 0.1613 0.5918 0.1889 0.090 Uiso 1 1 calc R . .
C15 C 0.1941(11) 0.6232(7) 0.2548(6) 0.058(3) Uani 1 1 d . . .
C16 C 0.1285(13) 0.5661(8) 0.3312(7) 0.082(4) Uani 1 1 d . . .
H16A H 0.0380 0.5549 0.3144 0.124 Uiso 1 1 calc R . .
H16B H 0.1335 0.6019 0.3876 0.124 Uiso 1 1 calc R . .
H16C H 0.1728 0.5058 0.3393 0.124 Uiso 1 1 calc R . .
C17 C 0.1009(11) 0.6964(7) 0.2122(6) 0.056(2) Uani 1 1 d . . .
C18 C 0.1288(12) 0.7910(7) 0.2062(7) 0.066(3) Uani 1 1 d . . .
H18A H 0.2100 0.8141 0.2267 0.079 Uiso 1 1 calc R . .
C19 C 0.0367(14) 0.8522(9) 0.1696(8) 0.080(3) Uani 1 1 d . . .
H19A H 0.0529 0.9179 0.1679 0.096 Uiso 1 1 calc R . .
C20 C -0.0795(14) 0.8162(9) 0.1357(7) 0.077(3) Uani 1 1 d . . .
H20A H -0.1429 0.8559 0.1088 0.092 Uiso 1 1 calc R . .
C21 C -0.0987(13) 0.7199(10) 0.1429(8) 0.083(4) Uani 1 1 d . . .
H21A H -0.1776 0.6947 0.1201 0.100 Uiso 1 1 calc R . .
N1 N 0.4419(9) 0.6178(5) 0.1233(5) 0.054(2) Uani 1 1 d . . .
N2 N 0.3506(8) 0.6716(5) -0.0398(5) 0.056(2) Uani 1 1 d . . .
N3 N 0.3128(10) 0.6722(6) 0.2916(6) 0.067(2) Uani 1 1 d . . .
N4 N -0.0113(10) 0.6590(7) 0.1807(6) 0.073(3) Uani 1 1 d . . .
Cl1 Cl 0.5497(4) 0.8436(2) 0.0844(2) 0.0880(10) Uani 1 1 d . . .
Cl2 Cl 0.6952(3) 0.6433(2) -0.05235(19) 0.0795(9) 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 2.052(8) . ?
Zn1 N2 2.055(8) . ?
Zn1 Cl1 2.189(3) . ?
Zn1 Cl2 2.201(3) . ?
C1 N2 1.354(12) . ?
C1 C2 1.364(15) . ?
C1 H1A 0.9300 . ?
C2 C3 1.353(16) . ?
C2 H2A 0.9300 . ?
C3 C4 1.378(15) . ?
C3 H3A 0.9300 . ?
C4 C5 1.345(14) . ?
C4 H4A 0.9300 . ?
C5 N2 1.356(12) . ?
C5 C6 1.497(13) . ?
C6 N1 1.275(12) . ?
C6 C14 1.497(13) . ?
C7 C8 1.379(15) . ?
C7 C12 1.404(14) . ?
C7 N1 1.419(12) . ?
C8 C9 1.378(15) . ?
C8 H8A 0.9300 . ?
C9 C10 1.359(16) . ?
C9 H9A 0.9300 . ?
C10 C11 1.379(16) . ?
C10 C13 1.515(15) . ?
C11 C12 1.413(14) . ?
C11 H11A 0.9300 . ?
C12 N3 1.390(13) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 N3 1.478(13) . ?
C15 C17 1.515(14) . ?
C15 C16 1.531(13) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 N4 1.327(13) . ?
C17 C18 1.352(13) . ?
C18 C19 1.366(15) . ?
C18 H18A 0.9300 . ?
C19 C20 1.367(17) . ?
C19 H19A 0.9300 . ?
C20 C21 1.361(16) . ?
C20 H20A 0.9300 . ?
C21 N4 1.339(15) . ?
C21 H21A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Zn1 N2 79.8(3) . . ?
N1 Zn1 Cl1 105.9(2) . . ?
N2 Zn1 Cl1 115.9(2) . . ?
N1 Zn1 Cl2 120.0(3) . . ?
N2 Zn1 Cl2 112.5(2) . . ?
Cl1 Zn1 Cl2 117.36(14) . . ?
N2 C1 C2 122.0(10) . . ?
N2 C1 H1A 119.0 . . ?
C2 C1 H1A 119.0 . . ?
C3 C2 C1 118.8(10) . . ?
C3 C2 H2A 120.6 . . ?
C1 C2 H2A 120.6 . . ?
C2 C3 C4 119.6(12) . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 H3A 120.2 . . ?
C5 C4 C3 120.2(11) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C4 C5 N2 120.9(9) . . ?
C4 C5 C6 125.4(10) . . ?
N2 C5 C6 113.7(9) . . ?
N1 C6 C5 117.4(9) . . ?
N1 C6 C14 122.8(9) . . ?
C5 C6 C14 119.7(10) . . ?
C8 C7 C12 121.7(10) . . ?
C8 C7 N1 116.6(9) . . ?
C12 C7 N1 121.3(10) . . ?
C7 C8 C9 121.5(12) . . ?
C7 C8 H8A 119.3 . . ?
C9 C8 H8A 119.3 . . ?
C10 C9 C8 118.1(13) . . ?
C10 C9 H9A 120.9 . . ?
C8 C9 H9A 120.9 . . ?
C9 C10 C11 121.7(11) . . ?
C9 C10 C13 118.1(13) . . ?
C11 C10 C13 120.2(12) . . ?
C10 C11 C12 121.7(11) . . ?
C10 C11 H11A 119.1 . . ?
C12 C11 H11A 119.1 . . ?
N3 C12 C7 123.1(9) . . ?
N3 C12 C11 121.5(10) . . ?
C7 C12 C11 115.2(11) . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C6 C14 H14A 109.5 . . ?
C6 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C6 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 C17 109.7(8) . . ?
N3 C15 C16 110.1(9) . . ?
C17 C15 C16 111.4(9) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N4 C17 C18 122.7(10) . . ?
N4 C17 C15 113.8(9) . . ?
C18 C17 C15 123.5(10) . . ?
C17 C18 C19 119.4(12) . . ?
C17 C18 H18A 120.3 . . ?
C19 C18 H18A 120.3 . . ?
C18 C19 C20 119.4(12) . . ?
C18 C19 H19A 120.3 . . ?
C20 C19 H19A 120.3 . . ?
C19 C20 C21 117.4(12) . . ?
C19 C20 H20A 121.3 . . ?
C21 C20 H20A 121.3 . . ?
N4 C21 C20 124.1(12) . . ?
N4 C21 H21A 117.9 . . ?
C20 C21 H21A 117.9 . . ?
C6 N1 C7 120.8(9) . . ?
C6 N1 Zn1 114.5(6) . . ?
C7 N1 Zn1 123.0(7) . . ?
C1 N2 C5 118.5(9) . . ?
C1 N2 Zn1 127.9(7) . . ?
C5 N2 Zn1 113.7(6) . . ?
C12 N3 C15 122.3(8) . . ?
C17 N4 C21 116.8(10) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.651
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.087
####################################################################### 
# 
# 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_c
_database_code_depnum_ccdc_archive 'CCDC 933235'
_audit_update_record             
;
2013-04-10 deposited with the CCDC.
2015-03-23 downloaded from the CCDC.
;
#TrackingRef 'Zn3.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H20 Cl4 N4 Zn2'
_chemical_formula_weight         564.92

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'
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                   8.3360(17)
_cell_length_b                   12.047(2)
_cell_length_c                   13.642(3)
_cell_angle_alpha                112.40(3)
_cell_angle_beta                 90.10(3)
_cell_angle_gamma                110.13(3)
_cell_volume                     1175.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11172
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    2.507
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7876
_exptl_absorpt_correction_T_max  0.7876
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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 II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11172
_diffrn_reflns_av_R_equivalents  0.2114
_diffrn_reflns_av_sigmaI/netI    0.5799
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5317
_reflns_number_gt                1162
_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    SHELXP-97
_computing_publication_material  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)+(0.1000P)²+0.0000P] 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         5317
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1910
_refine_ls_R_factor_gt           0.0880
_refine_ls_wR_factor_ref         0.3098
_refine_ls_wR_factor_gt          0.2243
_refine_ls_goodness_of_fit_ref   0.723
_refine_ls_restrained_S_all      0.723
_refine_ls_shift/su_max          0.172
_refine_ls_shift/su_mean         0.026

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 0.7550(2) 0.77237(16) 0.26836(11) 0.0830(7) Uani 1 1 d . . .
Zn2 Zn 0.9828(3) 1.22904(16) 0.23142(11) 0.0831(7) Uani 1 1 d . . .
C1 C 0.404(2) 0.6018(13) 0.1238(12) 0.106(7) Uani 1 1 d . . .
H1A H 0.3743 0.5699 0.1762 0.127 Uiso 1 1 calc R . .
C2 C 0.282(2) 0.5560(13) 0.0327(12) 0.091(5) Uani 1 1 d . . .
H2A H 0.1747 0.5588 0.0560 0.109 Uiso 1 1 d R . .
C3 C 0.332(2) 0.6340(12) -0.0373(10) 0.078(4) Uani 1 1 d . . .
H3A H 0.2501 0.6277 -0.0877 0.094 Uiso 1 1 calc R . .
C4 C 0.4960(19) 0.7103(13) -0.0220(8) 0.069(4) Uani 1 1 d . . .
H4A H 0.5351 0.7449 -0.0718 0.083 Uiso 1 1 calc R . .
C5 C 0.6101(16) 0.7398(10) 0.0647(7) 0.045(3) Uani 1 1 d . . .
C6 C 0.7869(15) 0.8289(10) 0.0877(7) 0.047(3) Uani 1 1 d . . .
H6A H 0.8324 0.8622 0.0381 0.056 Uiso 1 1 calc R . .
C7 C 1.0613(17) 0.9450(14) 0.1914(8) 0.080(5) Uani 1 1 d . . .
H7A H 1.0786 0.9869 0.1411 0.096 Uiso 1 1 calc R . .
C8 C 1.175(2) 0.8642(14) 0.1733(10) 0.086(5) Uani 1 1 d . . .
H8A H 1.1424 0.7984 0.1004 0.104 Uiso 1 1 calc R . .
H8B H 1.1533 0.8205 0.2216 0.104 Uiso 1 1 calc R . .
C9 C 1.368(2) 0.946(2) 0.1921(12) 0.163(11) Uani 1 1 d . . .
H9A H 1.3920 0.9879 0.1424 0.196 Uiso 1 1 calc R . .
H9B H 1.4350 0.8918 0.1802 0.196 Uiso 1 1 calc R . .
C10 C 1.418(2) 1.049(2) 0.3075(12) 0.192(13) Uani 1 1 d . . .
H10A H 1.5413 1.0997 0.3212 0.230 Uiso 1 1 calc R . .
H10B H 1.3940 1.0068 0.3570 0.230 Uiso 1 1 calc R . .
C11 C 1.3120(17) 1.1405(13) 0.3257(10) 0.080(5) Uani 1 1 d . . .
H11A H 1.3304 1.1793 0.2741 0.096 Uiso 1 1 calc R . .
H11B H 1.3479 1.2091 0.3974 0.096 Uiso 1 1 calc R . .
C12 C 1.1145(16) 1.0509(15) 0.3102(8) 0.090(6) Uani 1 1 d . . .
H12A H 1.0926 1.0121 0.3627 0.108 Uiso 1 1 calc R . .
C13 C 0.9555(14) 1.1688(10) 0.4136(7) 0.048(3) Uani 1 1 d . . .
H13A H 0.9631 1.1313 0.4609 0.058 Uiso 1 1 calc R . .
C14 C 0.8700(15) 1.2602(12) 0.4347(7) 0.053(3) Uani 1 1 d . . .
C15 C 0.7836(17) 1.2887(13) 0.5231(8) 0.070(4) Uani 1 1 d . . .
H15A H 0.7834 1.2515 0.5716 0.084 Uiso 1 1 calc R . .
C16 C 0.700(2) 1.3712(14) 0.5377(10) 0.086(5) Uani 1 1 d . . .
H16A H 0.6349 1.3872 0.5931 0.103 Uiso 1 1 calc R . .
C17 C 0.716(2) 1.4330(15) 0.4648(13) 0.097(5) Uani 1 1 d . . .
H17A H 0.6753 1.4993 0.4765 0.116 Uiso 1 1 calc R . .
C18 C 0.793(3) 1.3895(16) 0.3773(12) 0.113(7) Uani 1 1 d . . .
H18A H 0.7854 1.4184 0.3238 0.136 Uiso 1 1 calc R . .
N1 N 0.5639(15) 0.6908(11) 0.1374(7) 0.081(4) Uani 1 1 d . . .
N2 N 0.8816(12) 0.8624(7) 0.1753(6) 0.039(2) Uani 1 1 d . . .
N3 N 1.0212(11) 1.1422(7) 0.3247(6) 0.041(2) Uani 1 1 d . . .
N4 N 0.8760(15) 1.3118(8) 0.3612(7) 0.060(3) Uani 1 1 d . . .
Cl1 Cl 0.6764(7) 0.8926(4) 0.4119(3) 0.1222(19) Uani 1 1 d . . .
Cl2 Cl 0.8735(9) 0.6478(4) 0.2902(4) 0.186(3) Uani 1 1 d . . .
Cl3 Cl 1.2251(9) 1.3553(4) 0.2086(5) 0.187(3) Uani 1 1 d . . .
Cl4 Cl 0.7829(8) 1.1073(5) 0.0891(3) 0.136(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 N2 2.042(8) . ?
Zn1 N1 2.066(9) . ?
Zn1 Cl2 2.162(5) . ?
Zn1 Cl1 2.204(5) . ?
Zn2 N3 2.015(9) . ?
Zn2 N4 2.048(9) . ?
Zn2 Cl3 2.177(5) . ?
Zn2 Cl4 2.198(5) . ?
C1 N1 1.349(16) . ?
C1 C2 1.404(18) . ?
C1 H1A 0.9300 . ?
C2 C3 1.544(19) . ?
C2 H2A 0.9600 . ?
C3 C4 1.323(17) . ?
C3 H3A 0.9300 . ?
C4 C5 1.369(14) . ?
C4 H4A 0.9300 . ?
C5 N1 1.332(15) . ?
C5 C6 1.440(15) . ?
C6 N2 1.274(12) . ?
C6 H6A 0.9300 . ?
C7 N2 1.445(15) . ?
C7 C8 1.534(17) . ?
C7 C12 1.577(13) . ?
C7 H7A 0.9800 . ?
C8 C9 1.53(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.53(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.59(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.588(18) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N3 1.508(15) . ?
C12 H12A 0.9800 . ?
C13 N3 1.304(12) . ?
C13 C14 1.451(15) . ?
C13 H13A 0.9300 . ?
C14 N4 1.359(14) . ?
C14 C15 1.396(15) . ?
C15 C16 1.356(17) . ?
C15 H15A 0.9300 . ?
C16 C17 1.43(2) . ?
C16 H16A 0.9300 . ?
C17 C18 1.370(19) . ?
C17 H17A 0.9300 . ?
C18 N4 1.301(17) . ?
C18 H18A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Zn1 N1 80.0(4) . . ?
N2 Zn1 Cl2 111.8(3) . . ?
N1 Zn1 Cl2 117.0(4) . . ?
N2 Zn1 Cl1 116.4(3) . . ?
N1 Zn1 Cl1 110.3(4) . . ?
Cl2 Zn1 Cl1 116.4(2) . . ?
N3 Zn2 N4 80.0(4) . . ?
N3 Zn2 Cl3 112.1(3) . . ?
N4 Zn2 Cl3 116.3(3) . . ?
N3 Zn2 Cl4 116.3(3) . . ?
N4 Zn2 Cl4 110.3(4) . . ?
Cl3 Zn2 Cl4 116.6(2) . . ?
N1 C1 C2 121.8(11) . . ?
N1 C1 H1A 119.1 . . ?
C2 C1 H1A 119.1 . . ?
C1 C2 C3 114.5(11) . . ?
C1 C2 H2A 108.2 . . ?
C3 C2 H2A 108.1 . . ?
C4 C3 C2 116.7(13) . . ?
C4 C3 H3A 121.7 . . ?
C2 C3 H3A 121.7 . . ?
C3 C4 C5 122.1(13) . . ?
C3 C4 H4A 119.0 . . ?
C5 C4 H4A 118.9 . . ?
N1 C5 C4 122.1(12) . . ?
N1 C5 C6 114.2(9) . . ?
C4 C5 C6 123.7(11) . . ?
N2 C6 C5 120.6(10) . . ?
N2 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
N2 C7 C8 109.7(12) . . ?
N2 C7 C12 109.3(9) . . ?
C8 C7 C12 108.6(10) . . ?
N2 C7 H7A 109.8 . . ?
C8 C7 H7A 109.7 . . ?
C12 C7 H7A 109.7 . . ?
C7 C8 C9 112.6(14) . . ?
C7 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
C7 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 C10 108.8(13) . . ?
C8 C9 H9A 109.9 . . ?
C10 C9 H9A 109.9 . . ?
C8 C9 H9B 110.0 . . ?
C10 C9 H9B 110.0 . . ?
H9A C9 H9B 108.3 . . ?
C9 C10 C11 109.8(13) . . ?
C9 C10 H10A 109.7 . . ?
C11 C10 H10A 109.8 . . ?
C9 C10 H10B 109.7 . . ?
C11 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C10 C11 C12 106.1(13) . . ?
C10 C11 H11A 110.5 . . ?
C12 C11 H11A 110.4 . . ?
C10 C11 H11B 110.5 . . ?
C12 C11 H11B 110.5 . . ?
H11A C11 H11B 108.7 . . ?
N3 C12 C7 109.1(9) . . ?
N3 C12 C11 103.4(12) . . ?
C7 C12 C11 108.4(10) . . ?
N3 C12 H12A 111.8 . . ?
C7 C12 H12A 111.9 . . ?
C11 C12 H12A 111.8 . . ?
N3 C13 C14 116.2(10) . . ?
N3 C13 H13A 121.9 . . ?
C14 C13 H13A 121.9 . . ?
N4 C14 C15 123.2(12) . . ?
N4 C14 C13 115.4(10) . . ?
C15 C14 C13 121.3(11) . . ?
C16 C15 C14 119.5(13) . . ?
C16 C15 H15A 120.3 . . ?
C14 C15 H15A 120.3 . . ?
C15 C16 C17 117.7(14) . . ?
C15 C16 H16A 121.2 . . ?
C17 C16 H16A 121.1 . . ?
C18 C17 C16 116.7(14) . . ?
C18 C17 H17A 121.6 . . ?
C16 C17 H17A 121.7 . . ?
N4 C18 C17 126.6(14) . . ?
N4 C18 H18A 116.7 . . ?
C17 C18 H18A 116.7 . . ?
C5 N1 C1 120.6(10) . . ?
C5 N1 Zn1 112.7(8) . . ?
C1 N1 Zn1 126.6(10) . . ?
C6 N2 C7 118.4(10) . . ?
C6 N2 Zn1 112.3(8) . . ?
C7 N2 Zn1 128.9(7) . . ?
C13 N3 C12 113.4(9) . . ?
C13 N3 Zn2 115.4(8) . . ?
C12 N3 Zn2 131.2(7) . . ?
C18 N4 C14 115.6(11) . . ?
C18 N4 Zn2 131.0(9) . . ?
C14 N4 Zn2 112.5(8) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.993
_refine_diff_density_rms         0.187
####################################################################### 
# 
# 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_1d
_database_code_depnum_ccdc_archive 'CCDC 933236'
_audit_update_record             
;
2013-04-10 deposited with the CCDC.
2015-03-23 downloaded from the CCDC.
;
#TrackingRef 'Zn5.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H24 Cl4 N4 O2 Zn2'
_chemical_formula_weight         624.97

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   'C 2/c'

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

_cell_length_a                   23.119(5)
_cell_length_b                   8.2756(17)
_cell_length_c                   13.429(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.56(3)
_cell_angle_gamma                90.00
_cell_volume                     2569.2(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2938
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1264
_exptl_absorpt_coefficient_mu    2.307
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5643
_exptl_absorpt_correction_T_max  0.6554
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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 Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            12268
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2938
_reflns_number_gt                2486
_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    SHELXP-97
_computing_publication_material  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)+(0.0378P)²+3.1723P] 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         2938
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0768
_refine_ls_wR_factor_gt          0.0727
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_restrained_S_all      0.976
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001

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 0.607557(11) 0.86322(3) 0.840868(18) 0.03772(10) Uani 1 1 d . . .
O1 O 0.70443(8) 0.5921(2) 0.83465(14) 0.0590(5) Uani 1 1 d . . .
Cl1 Cl 0.66586(3) 1.04815(10) 0.90344(7) 0.0732(2) Uani 1 1 d . . .
Cl2 Cl 0.55307(3) 0.72737(11) 0.94562(5) 0.0687(2) Uani 1 1 d . . .
N1 N 0.56090(7) 0.9446(2) 0.71704(12) 0.0298(4) Uani 1 1 d . . .
N2 N 0.64142(7) 0.7124(2) 0.73292(13) 0.0333(4) Uani 1 1 d . . .
C1 C 0.52363(13) 1.3910(3) 0.7108(2) 0.0545(7) Uani 1 1 d . . .
H1A H 0.5483 1.4839 0.7162 0.082 Uiso 1 1 d R . .
H1B H 0.5032 1.3937 0.6482 0.082 Uiso 1 1 d R . .
C2 C 0.55998(10) 1.2384(3) 0.71637(19) 0.0435(5) Uani 1 1 d . . .
H2A H 0.5815 1.2372 0.7788 0.052 Uiso 1 1 calc R . .
H2B H 0.5877 1.2388 0.6626 0.052 Uiso 1 1 calc R . .
C3 C 0.52271(9) 1.0861(3) 0.70908(15) 0.0314(4) Uani 1 1 d . . .
H3A H 0.5047(10) 1.085(3) 0.6453(19) 0.038 Uiso 1 1 d . . .
C4 C 0.57336(9) 0.8660(3) 0.63871(15) 0.0332(4) Uani 1 1 d . . .
H4 H 0.5565 0.8943 0.5780 0.040 Uiso 1 1 calc R . .
C5 C 0.61422(9) 0.7308(3) 0.64384(15) 0.0321(4) Uani 1 1 d . . .
C6 C 0.62336(11) 0.6280(3) 0.56510(18) 0.0437(5) Uani 1 1 d . . .
H6A H 0.6044 0.6431 0.5044 0.052 Uiso 1 1 calc R . .
C7 C 0.66182(11) 0.5004(3) 0.57918(19) 0.0496(6) Uani 1 1 d . . .
H7A H 0.6681 0.4273 0.5278 0.059 Uiso 1 1 calc R . .
C8 C 0.69041(11) 0.4820(3) 0.6683(2) 0.0466(6) Uani 1 1 d . . .
H8A H 0.7166 0.3980 0.6780 0.056 Uiso 1 1 calc R . .
C9 C 0.67920(10) 0.5925(3) 0.74404(17) 0.0388(5) Uani 1 1 d . . .
C10 C 0.74850(14) 0.4729(4) 0.8545(2) 0.0768(10) Uani 1 1 d . . .
H10A H 0.7630 0.4864 0.9212 0.115 Uiso 1 1 calc R . .
H10B H 0.7795 0.4861 0.8083 0.115 Uiso 1 1 calc R . .
H10C H 0.7323 0.3667 0.8473 0.115 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 N2 2.0724(17) . ?
Zn1 N1 2.0851(18) . ?
Zn1 Cl1 2.2007(9) . ?
Zn1 Cl2 2.2056(9) . ?
O1 C9 1.344(3) . ?
O1 C10 1.441(3) . ?
N1 C4 1.273(3) . ?
N1 C3 1.470(3) . ?
N2 C9 1.329(3) . ?
N2 C5 1.355(3) . ?
C1 C2 1.518(3) . ?
C1 C1 1.525(5) 2_656 ?
C1 H1A 0.9599 . ?
C1 H1B 0.9601 . ?
C2 C3 1.530(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C3 1.527(4) 2_656 ?
C3 H3A 0.95(3) . ?
C4 C5 1.465(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(3) . ?
C6 C7 1.392(4) . ?
C6 H6A 0.9300 . ?
C7 C8 1.369(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.395(3) . ?
C8 H8A 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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
N2 Zn1 N1 80.37(7) . . ?
N2 Zn1 Cl1 116.86(6) . . ?
N1 Zn1 Cl1 112.95(6) . . ?
N2 Zn1 Cl2 111.17(6) . . ?
N1 Zn1 Cl2 112.28(5) . . ?
Cl1 Zn1 Cl2 117.55(4) . . ?
C9 O1 C10 118.0(2) . . ?
C4 N1 C3 119.22(18) . . ?
C4 N1 Zn1 111.99(14) . . ?
C3 N1 Zn1 128.40(13) . . ?
C9 N2 C5 118.84(18) . . ?
C9 N2 Zn1 128.56(15) . . ?
C5 N2 Zn1 111.99(14) . . ?
C2 C1 C1 111.47(19) . 2_656 ?
C2 C1 H1A 109.6 . . ?
C1 C1 H1A 112.1 2_656 . ?
C2 C1 H1B 109.3 . . ?
C1 C1 H1B 104.8 2_656 . ?
H1A C1 H1B 109.5 . . ?
C1 C2 C3 111.8(2) . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
N1 C3 C2 108.31(17) . . ?
N1 C3 C3 111.37(14) . 2_656 ?
C2 C3 C3 110.17(15) . 2_656 ?
N1 C3 H3A 108.3(15) . . ?
C2 C3 H3A 108.1(15) . . ?
C3 C3 H3A 110.6(15) 2_656 . ?
N1 C4 C5 120.18(19) . . ?
N1 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N2 C5 C6 122.4(2) . . ?
N2 C5 C4 114.92(18) . . ?
C6 C5 C4 122.7(2) . . ?
C5 C6 C7 117.9(2) . . ?
C5 C6 H6A 121.1 . . ?
C7 C6 H6A 121.1 . . ?
C8 C7 C6 120.3(2) . . ?
C8 C7 H7A 119.8 . . ?
C6 C7 H7A 119.8 . . ?
C7 C8 C9 118.2(2) . . ?
C7 C8 H8A 120.9 . . ?
C9 C8 H8A 120.9 . . ?
N2 C9 O1 112.5(2) . . ?
N2 C9 C8 122.3(2) . . ?
O1 C9 C8 125.2(2) . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_1e
_database_code_depnum_ccdc_archive 'CCDC 933237'
_audit_update_record             
;
2013-04-10 deposited with the CCDC.
2015-03-23 downloaded from the CCDC.
;
#TrackingRef 'Zn6.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H17 Cl2 N4 O Zn'
_chemical_formula_weight         381.58

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                   11.587(2)
_cell_length_b                   11.786(2)
_cell_length_c                   13.422(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.55(3)
_cell_angle_gamma                90.00
_cell_volume                     1757.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    16766
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      27.46

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             780
_exptl_absorpt_coefficient_mu    1.704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5431
_exptl_absorpt_correction_T_max  0.7745
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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 Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            16766
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         27.46
_reflns_number_total             3992
_reflns_number_gt                3030
_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, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  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)+(0.0450P)²+0.3172P] 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         3992
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0912
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.041
_refine_ls_shift/su_mean         0.001

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 0.25429(2) 0.28489(2) 0.03684(2) 0.03989(10) Uani 1 1 d . . .
Cl1 Cl 0.42764(6) 0.21700(6) 0.13116(6) 0.0658(2) Uani 1 1 d . . .
Cl2 Cl 0.21094(7) 0.28275(6) -0.13432(5) 0.0645(2) Uani 1 1 d . . .
O1 O 0.35271(16) 0.53802(14) 0.05048(15) 0.0543(4) Uani 1 1 d . . .
N1 N 0.11065(17) 0.23292(15) 0.08931(14) 0.0373(4) Uani 1 1 d . . .
N2 N 0.20469(16) 0.43983(14) 0.08492(14) 0.0374(4) Uani 1 1 d . . .
N3 N 0.7237(4) 0.0890(4) 0.0103(4) 0.1349(16) Uani 1 1 d . . .
N4 N 0.1828(3) 0.6394(3) -0.2092(3) 0.0923(9) Uani 1 1 d . . .
C1 C 0.1047(2) 0.43094(19) 0.11770(17) 0.0394(5) Uani 1 1 d . . .
C2 C 0.0497(2) 0.5235(2) 0.1459(2) 0.0509(6) Uani 1 1 d . . .
H2A H -0.0185 0.5156 0.1688 0.061 Uiso 1 1 calc R . .
C3 C 0.0990(3) 0.6293(2) 0.1391(2) 0.0592(7) Uani 1 1 d . . .
H3A H 0.0629 0.6937 0.1568 0.071 Uiso 1 1 calc R . .
C4 C 0.2000(2) 0.6400(2) 0.1069(2) 0.0551(6) Uani 1 1 d . . .
H4A H 0.2333 0.7110 0.1025 0.066 Uiso 1 1 calc R . .
C5 C 0.2523(2) 0.54198(19) 0.08066(18) 0.0423(5) Uani 1 1 d . . .
C6 C 0.0606(2) 0.31450(19) 0.12199(18) 0.0417(5) Uani 1 1 d . . .
H6A H -0.0038 0.3009 0.1487 0.050 Uiso 1 1 calc R . .
C7 C 0.4171(3) 0.6432(2) 0.0491(3) 0.0689(8) Uani 1 1 d . . .
H7A H 0.4871 0.6284 0.0264 0.103 Uiso 1 1 calc R . .
H7B H 0.4413 0.6750 0.1178 0.103 Uiso 1 1 calc R . .
H7C H 0.3655 0.6957 0.0023 0.103 Uiso 1 1 calc R . .
C8 C 0.0687(2) 0.11687(19) 0.09846(18) 0.0467(6) Uani 1 1 d . . .
H8A H 0.0076 0.1187 0.1351 0.056 Uiso 1 1 calc R . .
H8B H 0.1355 0.0717 0.1391 0.056 Uiso 1 1 calc R . .
C9 C 0.0171(2) 0.06177(17) -0.00586(18) 0.0411(5) Uani 1 1 d . . .
H9A H 0.0760 0.0647 -0.0448 0.049 Uiso 1 1 calc R . .
H9B H -0.0536 0.1034 -0.0447 0.049 Uiso 1 1 calc R . .
C10 C 0.6280(4) -0.0210(4) 0.1307(3) 0.0983(13) Uani 1 1 d . . .
H10A H 0.5794 -0.0806 0.0914 0.118 Uiso 1 1 calc R . .
H10B H 0.5784 0.0287 0.1576 0.118 Uiso 1 1 calc R . .
H10C H 0.6896 -0.0532 0.1873 0.118 Uiso 1 1 calc R . .
C11 C 0.6830(3) 0.0424(3) 0.0645(4) 0.0844(11) Uani 1 1 d . . .
C12 C 0.3688(3) 0.5395(3) -0.2296(3) 0.0991(13) Uani 1 1 d . . .
H12A H 0.3748 0.4661 -0.1976 0.119 Uiso 1 1 calc R . .
H12B H 0.4393 0.5832 -0.1967 0.119 Uiso 1 1 calc R . .
H12C H 0.3623 0.5310 -0.3021 0.119 Uiso 1 1 calc R . .
C13 C 0.2649(3) 0.5964(3) -0.2182(2) 0.0633(7) Uani 1 1 d . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N2 2.0720(18) . ?
Zn1 N1 2.0758(18) . ?
Zn1 Cl1 2.1975(10) . ?
Zn1 Cl2 2.2075(9) . ?
O1 C5 1.337(3) . ?
O1 C7 1.449(3) . ?
N1 C6 1.264(3) . ?
N1 C8 1.468(3) . ?
N2 C5 1.332(3) . ?
N2 C1 1.356(3) . ?
N3 C11 1.118(5) . ?
N4 C13 1.115(4) . ?
C1 C2 1.370(3) . ?
C1 C6 1.471(3) . ?
C2 C3 1.385(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.364(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.396(3) . ?
C4 H4A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.504(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C9 1.529(4) 3 ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.441(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C12 C13 1.423(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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
N2 Zn1 N1 80.45(7) . . ?
N2 Zn1 Cl1 115.51(6) . . ?
N1 Zn1 Cl1 112.76(6) . . ?
N2 Zn1 Cl2 109.46(5) . . ?
N1 Zn1 Cl2 112.52(6) . . ?
Cl1 Zn1 Cl2 119.67(4) . . ?
C5 O1 C7 118.0(2) . . ?
C6 N1 C8 118.95(19) . . ?
C6 N1 Zn1 112.60(15) . . ?
C8 N1 Zn1 128.31(15) . . ?
C5 N2 C1 119.12(19) . . ?
C5 N2 Zn1 128.90(15) . . ?
C1 N2 Zn1 111.81(14) . . ?
N2 C1 C2 122.4(2) . . ?
N2 C1 C6 115.01(19) . . ?
C2 C1 C6 122.6(2) . . ?
C1 C2 C3 117.7(2) . . ?
C1 C2 H2A 121.1 . . ?
C3 C2 H2A 121.1 . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
C3 C4 C5 118.4(2) . . ?
C3 C4 H4A 120.8 . . ?
C5 C4 H4A 120.8 . . ?
N2 C5 O1 112.84(19) . . ?
N2 C5 C4 121.5(2) . . ?
O1 C5 C4 125.7(2) . . ?
N1 C6 C1 119.9(2) . . ?
N1 C6 H6A 120.1 . . ?
C1 C6 H6A 120.1 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C9 112.18(18) . . ?
N1 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 C9 111.2(2) . 3 ?
C8 C9 H9A 109.4 . . ?
C9 C9 H9A 109.4 3 . ?
C8 C9 H9B 109.4 . . ?
C9 C9 H9B 109.4 3 . ?
H9A C9 H9B 108.0 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C11 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 C10 177.5(5) . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C13 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N4 C13 C12 179.0(4) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.054



