# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

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

data_1a
_database_code_depnum_ccdc_archive 'CCDC 1473390'
_audit_update_record             
;
2016-04-11 deposited with the CCDC.
2016-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H25 Cl6 N4 O2 W'
_chemical_formula_weight         629.89

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'
W W -0.8490 6.8722 '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                   8.8051(16)
_cell_length_b                   13.364(2)
_cell_length_c                   9.6474(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.100(2)
_cell_angle_gamma                90.00
_cell_volume                     1085.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6589
_cell_measurement_theta_min      2.2085
_cell_measurement_theta_max      27.9195

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.928
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             610
_exptl_absorpt_coefficient_mu    6.072
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.4433
_exptl_absorpt_correction_T_max  0.5294
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1347 (selected reflections only, before parameter refinement)
 R(int) =  0.0302 (selected reflections only, after parameter refinement)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '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            10402
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         27.00
_reflns_number_total             2352
_reflns_number_gt                2040
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1996)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

_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. The following restraints
 were applied (given as SHELXL lines): 
 eqiv $1 x, 0.5-y, -0.5+z
 eqiv $2 2-x, 1-y, -z
 dfix -2.18 .01 h2c h4c h2b h4b h1 h5c h2b h4b_$1 h1 h5c_$2
 dfix 0.87 .01 o1 h1
;

_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)+(0.0343P)²+10.4459P] 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         2352
_refine_ls_number_parameters     109
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0891
_refine_ls_wR_factor_gt          0.0813
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.269
_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
C1 C 1.2633(8) 0.2787(5) 0.1050(8) 0.0260(14) Uani 1 1 d . . .
H1A H 1.3231 0.2177 0.1422 0.039 Uiso 1 1 calc R . .
H1B H 1.3181 0.3366 0.1599 0.039 Uiso 1 1 calc R . .
H1C H 1.2557 0.2870 0.0023 0.039 Uiso 1 1 calc R . .
C2 C 1.0650(9) 0.1660(5) 0.1541(7) 0.0312(16) Uani 1 1 d . . .
H2A H 1.1630 0.1265 0.1836 0.047 Uiso 1 1 calc R . .
H2B H 0.9914 0.1362 0.0673 0.047 Uiso 1 1 calc RD . .
H2C H 1.0156 0.1667 0.2328 0.047 Uiso 1 1 calc RD . .
C3 C 1.0022(8) 0.3474(5) 0.0775(6) 0.0184(12) Uani 1 1 d . . .
C4 C 0.8494(9) 0.3283(6) 0.2612(7) 0.0341(18) Uani 1 1 d . . .
H4A H 0.7401 0.3430 0.2604 0.051 Uiso 1 1 calc R . .
H4B H 0.9234 0.3677 0.3374 0.051 Uiso 1 1 calc RD . .
H4C H 0.8711 0.2569 0.2802 0.051 Uiso 1 1 calc RD . .
C5 C 0.7373(8) 0.4168(5) 0.0368(8) 0.0247(14) Uani 1 1 d . . .
H5A H 0.6510 0.4137 0.0817 0.037 Uiso 1 1 calc R . .
H5B H 0.6990 0.3924 -0.0632 0.037 Uiso 1 1 calc R . .
H5C H 0.7733 0.4862 0.0368 0.037 Uiso 1 1 calc RD . .
Cl1 Cl 0.5654(2) 0.16701(12) -0.01977(19) 0.0252(3) Uani 1 1 d . . .
Cl2 Cl 0.4450(2) 0.03356(14) 0.21572(17) 0.0252(3) Uani 1 1 d . . .
Cl3 Cl 0.23554(18) 0.03256(13) -0.12776(18) 0.0234(3) Uani 1 1 d . . .
N1 N 1.1032(7) 0.2711(4) 0.1212(6) 0.0191(11) Uani 1 1 d . . .
N2 N 0.8699(6) 0.3544(4) 0.1193(6) 0.0188(11) Uani 1 1 d . . .
O1 O 1.0326(6) 0.4122(3) -0.0097(5) 0.0206(10) Uani 1 1 d D . .
H1 H 1.013(4) 0.4711(16) 0.019(8) 0.025 Uiso 0.50 1 d PD A -1
W1 W 0.5000 0.0000 0.0000 0.01646(13) Uani 1 2 d S . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.467(8) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.500(9) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 O1 1.289(8) . ?
C3 N1 1.336(8) . ?
C3 N2 1.344(8) . ?
C4 N2 1.474(8) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 N2 1.465(8) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
Cl1 W1 2.3268(16) . ?
Cl2 W1 2.3152(16) . ?
Cl3 W1 2.3330(16) . ?
O1 H1 0.869(12) . ?
W1 Cl2 2.3152(16) 3_655 ?
W1 Cl1 2.3268(16) 3_655 ?
W1 Cl3 2.3330(16) 3_655 ?

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 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O1 C3 N1 118.2(6) . . ?
O1 C3 N2 120.9(6) . . ?
N1 C3 N2 120.9(6) . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 N1 C1 119.0(6) . . ?
C3 N1 C2 127.7(6) . . ?
C1 N1 C2 111.7(5) . . ?
C3 N2 C5 120.0(5) . . ?
C3 N2 C4 128.0(6) . . ?
C5 N2 C4 110.1(5) . . ?
C3 O1 H1 108(4) . . ?
Cl2 W1 Cl2 180.00(2) . 3_655 ?
Cl2 W1 Cl1 89.41(6) . 3_655 ?
Cl2 W1 Cl1 90.59(6) 3_655 3_655 ?
Cl2 W1 Cl1 90.59(6) . . ?
Cl2 W1 Cl1 89.41(6) 3_655 . ?
Cl1 W1 Cl1 180.00(2) 3_655 . ?
Cl2 W1 Cl3 89.92(6) . . ?
Cl2 W1 Cl3 90.08(6) 3_655 . ?
Cl1 W1 Cl3 89.40(6) 3_655 . ?
Cl1 W1 Cl3 90.60(6) . . ?
Cl2 W1 Cl3 90.08(6) . 3_655 ?
Cl2 W1 Cl3 89.92(6) 3_655 3_655 ?
Cl1 W1 Cl3 90.60(6) 3_655 3_655 ?
Cl1 W1 Cl3 89.40(6) . 3_655 ?
Cl3 W1 Cl3 180.00(8) . 3_655 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C3 N1 C1 17.6(9) . . . . ?
N2 C3 N1 C1 -164.6(6) . . . . ?
O1 C3 N1 C2 -146.4(6) . . . . ?
N2 C3 N1 C2 31.4(9) . . . . ?
O1 C3 N2 C5 17.6(9) . . . . ?
N1 C3 N2 C5 -160.2(6) . . . . ?
O1 C3 N2 C4 -145.0(7) . . . . ?
N1 C3 N2 C4 37.3(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O1 0.869(12) 1.61(3) 2.437(9) 159(7) 3_765

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         2.577
_refine_diff_density_min         -2.509
_refine_diff_density_rms         0.181
####################################################################### 
# 
# 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 1473391'
_audit_update_record             
;
2016-04-11 deposited with the CCDC.
2016-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H25 Cl6 N4 O2 W'
_chemical_formula_weight         822.05

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'
W W -0.8490 6.8722 '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                   10.165(4)
_cell_length_b                   11.202(4)
_cell_length_c                   15.614(8)
_cell_angle_alpha                97.210(6)
_cell_angle_beta                 105.984(6)
_cell_angle_gamma                114.048(4)
_cell_volume                     1502.4(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4649
_cell_measurement_theta_min      2.3025
_cell_measurement_theta_max      26.993

_exptl_crystal_description       plate
_exptl_crystal_colour            dark-brown
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.817
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             802
_exptl_absorpt_coefficient_mu    4.410
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5389
_exptl_absorpt_correction_T_max  0.6668
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1419 (selected reflections only, before parameter refinement)
 R(int) =  0.0487 (selected reflections only, after parameter refinement)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '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            14858
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0647
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5871
_reflns_number_gt                4477
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1996)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

_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. The following restraints
 were applied (given as SHELXL lines): 
 DFIX 0.87 0.02 N1 H100  N2 H200  N3 H300  N4 H400
 simu .01 c1 > n4
 dfix 0.84 .01 o1 h1
;

_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)+(0.0458P)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         5871
_refine_ls_number_parameters     367
_refine_ls_number_restraints     209
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0799
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_restrained_S_all      0.968
_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
W1 W 0.63166(3) 0.70126(3) 0.680621(15) 0.02767(9) Uani 1 1 d . . .
Cl1 Cl 0.84527(17) 0.73699(16) 0.81175(9) 0.0336(3) Uani 1 1 d . . .
Cl2 Cl 0.76928(18) 0.68886(16) 0.58579(9) 0.0350(3) Uani 1 1 d . . .
Cl3 Cl 0.52584(19) 0.47304(16) 0.66221(10) 0.0406(4) Uani 1 1 d . . .
Cl4 Cl 0.50480(17) 0.72495(17) 0.78187(9) 0.0354(3) Uani 1 1 d . . .
Cl5 Cl 0.74986(16) 0.93852(15) 0.70486(9) 0.0321(3) Uani 1 1 d . . .
Cl6 Cl 0.42946(17) 0.68148(16) 0.55693(9) 0.0347(3) Uani 1 1 d . . .
C1 C 0.8203(6) 0.2360(6) 0.2521(3) 0.0257(11) Uani 1 1 d U . .
C2 C 0.9527(7) 0.4695(6) 0.3527(4) 0.0277(12) Uani 1 1 d U . .
C3 C 1.0771(7) 0.5302(6) 0.3242(4) 0.0324(13) Uani 1 1 d U . .
H3 H 1.1048 0.4754 0.2888 0.039 Uiso 1 1 calc R . .
C4 C 1.1597(7) 0.6696(6) 0.3474(4) 0.0360(14) Uani 1 1 d U . .
H4 H 1.2421 0.7106 0.3260 0.043 Uiso 1 1 calc R . .
C5 C 1.1237(7) 0.7508(6) 0.4016(4) 0.0349(13) Uani 1 1 d U . .
H5 H 1.1819 0.8469 0.4181 0.042 Uiso 1 1 calc R . .
C6 C 1.0013(7) 0.6898(6) 0.4316(4) 0.0317(13) Uani 1 1 d U . .
H6 H 0.9772 0.7449 0.4695 0.038 Uiso 1 1 calc R . .
C7 C 0.9148(7) 0.5506(6) 0.4072(4) 0.0307(12) Uani 1 1 d U . .
H7 H 0.8303 0.5100 0.4270 0.037 Uiso 1 1 calc R . .
C8 C 0.7268(7) 0.0428(6) 0.3161(4) 0.0289(12) Uani 1 1 d U . .
C9 C 0.8288(7) 0.0036(6) 0.3673(4) 0.0335(13) Uani 1 1 d U . .
H9 H 0.9240 0.0240 0.3588 0.040 Uiso 1 1 calc R . .
C10 C 0.7899(8) -0.0670(7) 0.4320(4) 0.0427(15) Uani 1 1 d U . .
H10 H 0.8577 -0.0964 0.4669 0.051 Uiso 1 1 calc R . .
C11 C 0.6521(8) -0.0935(6) 0.4448(4) 0.0417(15) Uani 1 1 d U . .
H11 H 0.6251 -0.1421 0.4882 0.050 Uiso 1 1 calc R . .
C12 C 0.5542(8) -0.0501(7) 0.3955(4) 0.0393(14) Uani 1 1 d U . .
H12 H 0.4615 -0.0667 0.4061 0.047 Uiso 1 1 calc R . .
C13 C 0.5899(7) 0.0181(6) 0.3299(4) 0.0344(13) Uani 1 1 d U . .
H13 H 0.5217 0.0472 0.2952 0.041 Uiso 1 1 calc R . .
O1 O 0.8385(5) 0.2854(4) 0.1794(3) 0.0353(10) Uani 1 1 d DU . .
H1 H 0.802(7) 0.214(4) 0.138(3) 0.053 Uiso 1 1 d D . .
N1 N 0.8674(5) 0.3251(5) 0.3322(3) 0.0285(10) Uani 1 1 d DU . .
H100 H 0.863(7) 0.297(6) 0.381(3) 0.034 Uiso 1 1 d D . .
N2 N 0.7594(6) 0.1051(5) 0.2439(3) 0.0302(11) Uani 1 1 d DU . .
H200 H 0.731(7) 0.055(5) 0.189(2) 0.036 Uiso 1 1 d D . .
C21 C 0.2152(7) 0.9931(6) 0.9983(4) 0.0321(13) Uani 1 1 d U . .
C22 C 0.2082(7) 1.1894(6) 0.9438(4) 0.0304(12) Uani 1 1 d U . .
C23 C 0.1357(7) 1.1353(7) 0.8485(4) 0.0360(13) Uani 1 1 d U . .
H23 H 0.0789 1.0398 0.8223 0.043 Uiso 1 1 calc R . .
C24 C 0.1474(7) 1.2225(7) 0.7921(4) 0.0381(14) Uani 1 1 d U . .
H24 H 0.0981 1.1862 0.7268 0.046 Uiso 1 1 calc R . .
C25 C 0.2293(7) 1.3610(7) 0.8293(4) 0.0373(14) Uani 1 1 d U . .
H25 H 0.2382 1.4194 0.7897 0.045 Uiso 1 1 calc R . .
C26 C 0.2981(8) 1.4150(7) 0.9235(4) 0.0423(15) Uani 1 1 d U . .
H26 H 0.3524 1.5107 0.9492 0.051 Uiso 1 1 calc R . .
C27 C 0.2883(7) 1.3293(7) 0.9814(4) 0.0402(15) Uani 1 1 d U . .
H27 H 0.3363 1.3665 1.0466 0.048 Uiso 1 1 calc R . .
C28 C 0.2350(8) 0.8240(6) 1.0814(4) 0.0363(13) Uani 1 1 d U . .
C29 C 0.3804(8) 0.8391(7) 1.0853(4) 0.0401(14) Uani 1 1 d U . .
H29 H 0.4492 0.9158 1.0722 0.048 Uiso 1 1 calc R . .
C30 C 0.4230(9) 0.7419(8) 1.1083(4) 0.0500(16) Uani 1 1 d U . .
H30 H 0.5218 0.7522 1.1114 0.060 Uiso 1 1 calc R . .
C31 C 0.3225(9) 0.6290(8) 1.1271(4) 0.0515(17) Uani 1 1 d U . .
H31 H 0.3530 0.5627 1.1432 0.062 Uiso 1 1 calc R . .
C32 C 0.1777(10) 0.6130(8) 1.1222(5) 0.0534(17) Uani 1 1 d U . .
H32 H 0.1085 0.5354 1.1344 0.064 Uiso 1 1 calc R . .
C33 C 0.1338(9) 0.7116(7) 1.0992(4) 0.0456(15) Uani 1 1 d U . .
H33 H 0.0348 0.7013 1.0958 0.055 Uiso 1 1 calc R . .
O2 O 0.2513(5) 0.9505(4) 0.9349(2) 0.0352(10) Uani 1 1 d U . .
N3 N 0.1910(6) 1.1042(5) 1.0052(3) 0.0334(11) Uani 1 1 d DU . .
H300 H 0.197(7) 1.144(6) 1.058(2) 0.040 Uiso 1 1 d D . .
N4 N 0.1910(6) 0.9268(5) 1.0643(3) 0.0346(11) Uani 1 1 d DU . .
H400 H 0.162(7) 0.959(6) 1.105(3) 0.042 Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
W1 Cl3 2.2758(18) . ?
W1 Cl6 2.3105(16) . ?
W1 Cl2 2.3272(15) . ?
W1 Cl4 2.3514(15) . ?
W1 Cl5 2.3548(17) . ?
W1 Cl1 2.3884(16) . ?
C1 N2 1.311(7) . ?
C1 N1 1.324(7) . ?
C1 O1 1.349(6) . ?
C2 C3 1.394(8) . ?
C2 C7 1.404(8) . ?
C2 N1 1.430(7) . ?
C3 C4 1.377(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.377(8) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.382(8) . ?
C8 C13 1.388(8) . ?
C8 N2 1.444(7) . ?
C9 C10 1.403(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(9) . ?
C10 H10 0.9500 . ?
C11 C12 1.373(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.392(8) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
O1 H1 0.835(10) . ?
N1 H100 0.867(19) . ?
N2 H200 0.862(19) . ?
C21 O2 1.253(6) . ?
C21 N3 1.360(8) . ?
C21 N4 1.361(7) . ?
C22 C27 1.389(9) . ?
C22 C23 1.389(8) . ?
C22 N3 1.431(7) . ?
C23 C24 1.387(8) . ?
C23 H23 0.9500 . ?
C24 C25 1.375(9) . ?
C24 H24 0.9500 . ?
C25 C26 1.373(8) . ?
C25 H25 0.9500 . ?
C26 C27 1.391(9) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C33 1.382(9) . ?
C28 C29 1.401(9) . ?
C28 N4 1.425(8) . ?
C29 C30 1.377(9) . ?
C29 H29 0.9500 . ?
C30 C31 1.391(10) . ?
C30 H30 0.9500 . ?
C31 C32 1.387(10) . ?
C31 H31 0.9500 . ?
C32 C33 1.401(10) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
N3 H300 0.86(2) . ?
N4 H400 0.872(19) . ?

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
Cl3 W1 Cl6 92.93(6) . . ?
Cl3 W1 Cl2 91.47(6) . . ?
Cl6 W1 Cl2 91.53(6) . . ?
Cl3 W1 Cl4 90.96(6) . . ?
Cl6 W1 Cl4 90.40(6) . . ?
Cl2 W1 Cl4 176.81(6) . . ?
Cl3 W1 Cl5 177.63(6) . . ?
Cl6 W1 Cl5 89.44(5) . . ?
Cl2 W1 Cl5 88.44(5) . . ?
Cl4 W1 Cl5 89.04(5) . . ?
Cl3 W1 Cl1 90.64(6) . . ?
Cl6 W1 Cl1 176.27(6) . . ?
Cl2 W1 Cl1 89.47(6) . . ?
Cl4 W1 Cl1 88.44(6) . . ?
Cl5 W1 Cl1 87.00(5) . . ?
N2 C1 N1 121.5(5) . . ?
N2 C1 O1 121.2(5) . . ?
N1 C1 O1 117.3(5) . . ?
C3 C2 C7 119.9(5) . . ?
C3 C2 N1 121.3(5) . . ?
C7 C2 N1 118.7(5) . . ?
C4 C3 C2 119.9(5) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.7(6) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 119.3(6) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C7 C6 C5 120.9(5) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C2 119.3(5) . . ?
C6 C7 H7 120.4 . . ?
C2 C7 H7 120.4 . . ?
C9 C8 C13 121.3(5) . . ?
C9 C8 N2 119.6(5) . . ?
C13 C8 N2 119.1(5) . . ?
C8 C9 C10 119.0(6) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C11 C10 C9 119.6(6) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C12 C11 C10 120.6(6) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 120.5(6) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C8 C13 C12 118.9(6) . . ?
C8 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C1 O1 H1 101(5) . . ?
C1 N1 C2 126.5(4) . . ?
C1 N1 H100 119(4) . . ?
C2 N1 H100 113(4) . . ?
C1 N2 C8 125.0(5) . . ?
C1 N2 H200 115(4) . . ?
C8 N2 H200 120(4) . . ?
O2 C21 N3 123.5(5) . . ?
O2 C21 N4 121.6(6) . . ?
N3 C21 N4 114.8(5) . . ?
C27 C22 C23 119.9(5) . . ?
C27 C22 N3 118.6(5) . . ?
C23 C22 N3 121.3(6) . . ?
C24 C23 C22 119.2(6) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C25 C24 C23 120.9(6) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C26 C25 C24 120.2(6) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C27 119.9(6) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C22 C27 C26 120.0(6) . . ?
C22 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C33 C28 C29 120.4(6) . . ?
C33 C28 N4 118.4(6) . . ?
C29 C28 N4 121.1(6) . . ?
C30 C29 C28 119.5(7) . . ?
C30 C29 H29 120.2 . . ?
C28 C29 H29 120.2 . . ?
C29 C30 C31 120.5(7) . . ?
C29 C30 H30 119.7 . . ?
C31 C30 H30 119.7 . . ?
C32 C31 C30 120.1(7) . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C31 C32 C33 119.7(7) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 H32 120.1 . . ?
C28 C33 C32 119.7(7) . . ?
C28 C33 H33 120.1 . . ?
C32 C33 H33 120.1 . . ?
C21 N3 C22 125.0(5) . . ?
C21 N3 H300 118(4) . . ?
C22 N3 H300 113(4) . . ?
C21 N4 C28 124.8(5) . . ?
C21 N4 H400 118(4) . . ?
C28 N4 H400 116(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C2 C3 C4 -1.8(8) . . . . ?
N1 C2 C3 C4 -178.1(5) . . . . ?
C2 C3 C4 C5 2.2(9) . . . . ?
C3 C4 C5 C6 -0.8(9) . . . . ?
C4 C5 C6 C7 -0.9(9) . . . . ?
C5 C6 C7 C2 1.2(8) . . . . ?
C3 C2 C7 C6 0.1(8) . . . . ?
N1 C2 C7 C6 176.5(5) . . . . ?
C13 C8 C9 C10 2.3(9) . . . . ?
N2 C8 C9 C10 -174.8(5) . . . . ?
C8 C9 C10 C11 -1.3(9) . . . . ?
C9 C10 C11 C12 -0.7(10) . . . . ?
C10 C11 C12 C13 1.8(10) . . . . ?
C9 C8 C13 C12 -1.3(9) . . . . ?
N2 C8 C13 C12 175.8(5) . . . . ?
C11 C12 C13 C8 -0.7(9) . . . . ?
N2 C1 N1 C2 171.5(5) . . . . ?
O1 C1 N1 C2 -8.0(8) . . . . ?
C3 C2 N1 C1 -43.6(8) . . . . ?
C7 C2 N1 C1 140.1(6) . . . . ?
N1 C1 N2 C8 4.5(9) . . . . ?
O1 C1 N2 C8 -176.0(5) . . . . ?
C9 C8 N2 C1 -99.3(7) . . . . ?
C13 C8 N2 C1 83.5(8) . . . . ?
C27 C22 C23 C24 1.3(9) . . . . ?
N3 C22 C23 C24 175.7(6) . . . . ?
C22 C23 C24 C25 0.0(9) . . . . ?
C23 C24 C25 C26 -1.4(10) . . . . ?
C24 C25 C26 C27 1.6(10) . . . . ?
C23 C22 C27 C26 -1.1(10) . . . . ?
N3 C22 C27 C26 -175.7(6) . . . . ?
C25 C26 C27 C22 -0.4(10) . . . . ?
C33 C28 C29 C30 -0.9(9) . . . . ?
N4 C28 C29 C30 175.6(6) . . . . ?
C28 C29 C30 C31 0.4(10) . . . . ?
C29 C30 C31 C32 0.4(10) . . . . ?
C30 C31 C32 C33 -0.6(10) . . . . ?
C29 C28 C33 C32 0.7(9) . . . . ?
N4 C28 C33 C32 -175.9(6) . . . . ?
C31 C32 C33 C28 0.1(10) . . . . ?
O2 C21 N3 C22 -2.1(10) . . . . ?
N4 C21 N3 C22 -179.6(5) . . . . ?
C27 C22 N3 C21 -133.8(6) . . . . ?
C23 C22 N3 C21 51.7(9) . . . . ?
O2 C21 N4 C28 14.3(10) . . . . ?
N3 C21 N4 C28 -168.1(6) . . . . ?
C33 C28 N4 C21 -138.9(6) . . . . ?
C29 C28 N4 C21 44.6(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.835(10) 1.816(19) 2.638(6) 168(7) 2_666
N2 H200 O2 0.862(19) 1.99(4) 2.744(6) 146(5) 2_666
N3 H300 Cl1 0.86(2) 2.52(3) 3.363(5) 165(6) 2_677
N4 H400 Cl5 0.872(19) 2.78(4) 3.512(5) 142(5) 2_677

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.539
_refine_diff_density_min         -2.082
_refine_diff_density_rms         0.142
####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 1473392'
_audit_update_record             
;
2016-04-11 deposited with the CCDC.
2016-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H8 Cl5 N2 O W'
_chemical_formula_weight         449.21

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'
W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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'

_cell_length_a                   10.180(3)
_cell_length_b                   15.365(4)
_cell_length_c                   22.009(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3442.5(17)
_cell_formula_units_Z            12
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8629
_cell_measurement_theta_min      2.400
_cell_measurement_theta_max      26.2315

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.600
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2484
_exptl_absorpt_coefficient_mu    11.190
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.2250
_exptl_absorpt_correction_T_max  0.4008
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1801 (selected reflections only, before parameter refinement)
 R(int) =  0.0999 (selected reflections only, after parameter refinement)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '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            30675
_diffrn_reflns_av_R_equivalents  0.1196
_diffrn_reflns_av_unetI/netI     0.0872
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         25.03
_reflns_number_total             6061
_reflns_number_gt                4860
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1996)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

_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. The following restraints
 were applied (given as SHELXL lines): 
 simu .01 c1 > o3
 isor n4
 dfix 0.89 n1 h1 n2 h2 n3 h3 n4 h4 n5 h5 n6 h6
;

_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)+(0.0298P)²+18.9867P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.035(13)
_refine_ls_number_reflns         6061
_refine_ls_number_parameters     344
_refine_ls_number_restraints     102
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.0997
_refine_ls_wR_factor_gt          0.0898
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1867(15) 0.2904(9) 0.3958(7) 0.018(3) Uani 1 1 d U . .
C2 C -0.0455(17) 0.3305(11) 0.4030(7) 0.033(4) Uani 1 1 d U . .
H2A H -0.1014 0.3777 0.3879 0.049 Uiso 1 1 calc R . .
H2B H -0.0477 0.3297 0.4475 0.049 Uiso 1 1 calc R . .
H2C H -0.0779 0.2747 0.3873 0.049 Uiso 1 1 calc R . .
C3 C 0.2669(19) 0.1549(11) 0.4428(9) 0.041(5) Uani 1 1 d U . .
H3A H 0.2317 0.1105 0.4703 0.062 Uiso 1 1 calc R . .
H3B H 0.3440 0.1823 0.4615 0.062 Uiso 1 1 calc R . .
H3C H 0.2925 0.1278 0.4043 0.062 Uiso 1 1 calc R . .
C4 C 0.8103(15) 0.8599(10) 0.4298(7) 0.023(3) Uani 1 1 d U . .
C5 C 1.0146(15) 0.9068(10) 0.4756(8) 0.032(4) Uani 1 1 d U . .
H5A H 1.0454 0.9575 0.4986 0.048 Uiso 1 1 calc R . .
H5B H 1.0668 0.9007 0.4385 0.048 Uiso 1 1 calc R . .
H5C H 1.0243 0.8543 0.5005 0.048 Uiso 1 1 calc R . .
C6 C 0.7759(18) 0.7225(11) 0.3765(9) 0.039(4) Uani 1 1 d U . .
H6A H 0.8259 0.6687 0.3701 0.059 Uiso 1 1 calc R . .
H6B H 0.7562 0.7493 0.3371 0.059 Uiso 1 1 calc R . .
H6C H 0.6936 0.7089 0.3976 0.059 Uiso 1 1 calc R . .
C7 C 0.2977(17) 0.6440(10) 0.2615(7) 0.027(3) Uani 1 1 d U . .
C8 C 0.2046(19) 0.7876(12) 0.2862(10) 0.052(5) Uani 1 1 d U . .
H8A H 0.2385 0.8463 0.2936 0.077 Uiso 1 1 calc R . .
H8B H 0.1572 0.7671 0.3222 0.077 Uiso 1 1 calc R . .
H8C H 0.1446 0.7887 0.2514 0.077 Uiso 1 1 calc R . .
C9 C 0.5274(18) 0.6165(11) 0.2525(7) 0.037(4) Uani 1 1 d U . .
H9A H 0.5828 0.5669 0.2413 0.056 Uiso 1 1 calc R . .
H9B H 0.5477 0.6344 0.2942 0.056 Uiso 1 1 calc R . .
H9C H 0.5443 0.6651 0.2248 0.056 Uiso 1 1 calc R . .
N1 N 0.0890(12) 0.3442(8) 0.3824(6) 0.022(3) Uani 1 1 d DU . .
H1 H 0.116(15) 0.387(7) 0.358(5) 0.027 Uiso 1 1 d D . .
N2 N 0.1666(13) 0.2210(8) 0.4315(6) 0.021(3) Uani 1 1 d DU . .
H2 H 0.089(7) 0.196(9) 0.435(7) 0.025 Uiso 1 1 d D . .
N3 N 0.8787(12) 0.9184(8) 0.4599(6) 0.023(3) Uani 1 1 d DU . .
H3 H 0.812(10) 0.947(9) 0.476(6) 0.027 Uiso 1 1 d D . .
N4 N 0.8555(13) 0.7845(9) 0.4143(6) 0.025(3) Uani 1 1 d DU . .
H4 H 0.939(5) 0.767(9) 0.418(7) 0.030 Uiso 1 1 d D . .
N5 N 0.3146(15) 0.7284(9) 0.2732(7) 0.033(3) Uani 1 1 d DU . .
H5 H 0.393(8) 0.749(10) 0.262(7) 0.040 Uiso 1 1 d D . .
N6 N 0.3939(14) 0.5922(9) 0.2487(6) 0.025(3) Uani 1 1 d DU . .
H6 H 0.378(16) 0.536(3) 0.242(7) 0.031 Uiso 1 1 d D . .
O1 O 0.2999(9) 0.3044(6) 0.3724(4) 0.018(2) Uani 1 1 d U . .
O2 O 0.6845(10) 0.8813(7) 0.4143(5) 0.024(2) Uani 1 1 d U . .
O3 O 0.1775(11) 0.6130(7) 0.2690(5) 0.030(3) Uani 1 1 d U . .
Cl1 Cl 0.6367(4) 0.4607(3) 0.3911(2) 0.0330(11) Uani 1 1 d . . .
Cl2 Cl 0.4264(4) 0.3656(3) 0.48743(16) 0.0230(9) Uani 1 1 d . . .
Cl3 Cl 0.3236(4) 0.4968(2) 0.38043(18) 0.0219(9) Uani 1 1 d . . .
Cl4 Cl 0.4712(4) 0.3756(2) 0.27443(15) 0.0264(8) Uani 1 1 d . . .
Cl5 Cl 0.5874(4) 0.2506(3) 0.38537(19) 0.0257(9) Uani 1 1 d . . .
Cl6 Cl 0.3357(4) 0.9333(3) 0.5074(2) 0.0339(11) Uani 1 1 d . . .
Cl7 Cl 0.6130(4) 0.8324(3) 0.53891(19) 0.0289(9) Uani 1 1 d . . .
Cl8 Cl 0.4327(4) 0.7739(3) 0.4192(2) 0.0380(11) Uani 1 1 d . . .
Cl9 Cl 0.4499(4) 0.9708(3) 0.36507(16) 0.0313(10) Uani 1 1 d . . .
Cl10 Cl 0.6076(4) 1.0378(3) 0.48626(18) 0.0241(9) Uani 1 1 d . . .
Cl11 Cl -0.1217(5) 0.4949(3) 0.1691(3) 0.0536(14) Uani 1 1 d . . .
Cl12 Cl -0.0527(5) 0.5220(3) 0.3192(2) 0.0464(13) Uani 1 1 d . . .
Cl13 Cl -0.0852(5) 0.6859(3) 0.2252(2) 0.0412(12) Uani 1 1 d . . .
Cl14 Cl 0.1512(5) 0.5983(3) 0.13809(18) 0.0341(10) Uani 1 1 d . . .
Cl15 Cl 0.1506(4) 0.4247(2) 0.22759(18) 0.0274(10) Uani 1 1 d . . .
W1 W 0.45713(6) 0.37382(4) 0.38084(3) 0.01697(15) Uani 1 1 d . . .
W2 W 0.52164(7) 0.90529(4) 0.45340(3) 0.02091(16) Uani 1 1 d . . .
W3 W 0.03622(8) 0.55681(4) 0.22551(3) 0.02571(17) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.280(17) . ?
C1 N1 1.327(19) . ?
C1 N2 1.340(18) . ?
C2 N1 1.46(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 N2 1.46(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 N4 1.292(19) . ?
C4 N3 1.32(2) . ?
C4 O2 1.365(18) . ?
C5 N3 1.437(19) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 N4 1.50(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 N6 1.29(2) . ?
C7 O3 1.323(19) . ?
C7 N5 1.33(2) . ?
C8 N5 1.47(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 N6 1.41(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
N1 H1 0.89(2) . ?
N2 H2 0.89(2) . ?
N3 H3 0.89(2) . ?
N4 H4 0.89(2) . ?
N5 H5 0.89(2) . ?
N6 H6 0.89(2) . ?
O1 W1 1.932(10) . ?
O2 W2 1.905(10) . ?
O3 W3 1.932(11) . ?
Cl1 W1 2.275(4) . ?
Cl2 W1 2.370(4) . ?
Cl3 W1 2.328(4) . ?
Cl4 W1 2.347(3) . ?
Cl5 W1 2.314(4) . ?
Cl6 W2 2.276(4) . ?
Cl7 W2 2.380(4) . ?
Cl8 W2 2.337(4) . ?
Cl9 W2 2.307(4) . ?
Cl10 W2 2.331(4) . ?
Cl11 W3 2.243(5) . ?
Cl12 W3 2.315(4) . ?
Cl13 W3 2.337(4) . ?
Cl14 W3 2.341(4) . ?
Cl15 W3 2.340(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 118.8(13) . . ?
O1 C1 N2 120.5(14) . . ?
N1 C1 N2 120.7(14) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N4 C4 N3 123.8(15) . . ?
N4 C4 O2 118.9(14) . . ?
N3 C4 O2 117.2(13) . . ?
N3 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N4 C6 H6A 109.5 . . ?
N4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N6 C7 O3 120.4(15) . . ?
N6 C7 N5 122.9(16) . . ?
O3 C7 N5 116.4(15) . . ?
N5 C8 H8A 109.5 . . ?
N5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N6 C9 H9A 109.5 . . ?
N6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 N1 C2 123.1(13) . . ?
C1 N1 H1 111(10) . . ?
C2 N1 H1 126(10) . . ?
C1 N2 C3 123.1(14) . . ?
C1 N2 H2 122(10) . . ?
C3 N2 H2 108(10) . . ?
C4 N3 C5 123.1(14) . . ?
C4 N3 H3 98(10) . . ?
C5 N3 H3 135(10) . . ?
C4 N4 C6 121.5(14) . . ?
C4 N4 H4 125(10) . . ?
C6 N4 H4 112(10) . . ?
C7 N5 C8 122.8(15) . . ?
C7 N5 H5 114(10) . . ?
C8 N5 H5 121(10) . . ?
C7 N6 C9 123.5(15) . . ?
C7 N6 H6 119(10) . . ?
C9 N6 H6 116(10) . . ?
C1 O1 W1 143.2(10) . . ?
C4 O2 W2 138.6(10) . . ?
C7 O3 W3 141.9(10) . . ?
O1 W1 Cl1 177.5(3) . . ?
O1 W1 Cl5 91.6(3) . . ?
Cl1 W1 Cl5 90.90(16) . . ?
O1 W1 Cl3 87.9(3) . . ?
Cl1 W1 Cl3 89.61(15) . . ?
Cl5 W1 Cl3 177.64(15) . . ?
O1 W1 Cl4 87.8(3) . . ?
Cl1 W1 Cl4 92.48(16) . . ?
Cl5 W1 Cl4 90.99(14) . . ?
Cl3 W1 Cl4 91.29(13) . . ?
O1 W1 Cl2 87.5(3) . . ?
Cl1 W1 Cl2 92.23(15) . . ?
Cl5 W1 Cl2 89.41(14) . . ?
Cl3 W1 Cl2 88.27(13) . . ?
Cl4 W1 Cl2 175.27(15) . . ?
O2 W2 Cl6 175.4(3) . . ?
O2 W2 Cl9 88.8(3) . . ?
Cl6 W2 Cl9 95.39(15) . . ?
O2 W2 Cl10 89.0(3) . . ?
Cl6 W2 Cl10 89.15(15) . . ?
Cl9 W2 Cl10 89.97(15) . . ?
O2 W2 Cl8 91.4(3) . . ?
Cl6 W2 Cl8 90.53(17) . . ?
Cl9 W2 Cl8 89.01(16) . . ?
Cl10 W2 Cl8 178.90(16) . . ?
O2 W2 Cl7 85.8(3) . . ?
Cl6 W2 Cl7 90.08(15) . . ?
Cl9 W2 Cl7 174.44(15) . . ?
Cl10 W2 Cl7 91.09(15) . . ?
Cl8 W2 Cl7 89.96(16) . . ?
O3 W3 Cl11 176.1(3) . . ?
O3 W3 Cl12 87.3(3) . . ?
Cl11 W3 Cl12 96.6(2) . . ?
O3 W3 Cl13 90.9(3) . . ?
Cl11 W3 Cl13 88.81(19) . . ?
Cl12 W3 Cl13 89.53(16) . . ?
O3 W3 Cl15 90.4(3) . . ?
Cl11 W3 Cl15 89.98(17) . . ?
Cl12 W3 Cl15 88.66(14) . . ?
Cl13 W3 Cl15 177.69(16) . . ?
O3 W3 Cl14 85.0(3) . . ?
Cl11 W3 Cl14 91.11(18) . . ?
Cl12 W3 Cl14 172.24(18) . . ?
Cl13 W3 Cl14 91.79(16) . . ?
Cl15 W3 Cl14 90.20(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 N1 C2 175.4(14) . . . . ?
N2 C1 N1 C2 -3(2) . . . . ?
O1 C1 N2 C3 -4(2) . . . . ?
N1 C1 N2 C3 173.8(15) . . . . ?
N4 C4 N3 C5 4(3) . . . . ?
O2 C4 N3 C5 -175.8(13) . . . . ?
N3 C4 N4 C6 -176.1(16) . . . . ?
O2 C4 N4 C6 4(2) . . . . ?
N6 C7 N5 C8 178.3(17) . . . . ?
O3 C7 N5 C8 -8(3) . . . . ?
O3 C7 N6 C9 -166.2(15) . . . . ?
N5 C7 N6 C9 8(3) . . . . ?
N1 C1 O1 W1 80(2) . . . . ?
N2 C1 O1 W1 -101.6(18) . . . . ?
N4 C4 O2 W2 114.5(16) . . . . ?
N3 C4 O2 W2 -66(2) . . . . ?
N6 C7 O3 W3 -66(2) . . . . ?
N5 C7 O3 W3 120.0(17) . . . . ?
C1 O1 W1 Cl1 -48(8) . . . . ?
C1 O1 W1 Cl5 124.5(16) . . . . ?
C1 O1 W1 Cl3 -53.2(16) . . . . ?
C1 O1 W1 Cl4 -144.6(16) . . . . ?
C1 O1 W1 Cl2 35.1(16) . . . . ?
C4 O2 W2 Cl6 6(5) . . . . ?
C4 O2 W2 Cl9 161.8(14) . . . . ?
C4 O2 W2 Cl10 71.8(14) . . . . ?
C4 O2 W2 Cl8 -109.2(14) . . . . ?
C4 O2 W2 Cl7 -19.4(14) . . . . ?
C7 O3 W3 Cl11 -20(6) . . . . ?
C7 O3 W3 Cl12 164.4(17) . . . . ?
C7 O3 W3 Cl13 -106.1(17) . . . . ?
C7 O3 W3 Cl15 75.8(17) . . . . ?
C7 O3 W3 Cl14 -14.4(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 Cl3 0.89(2) 2.75(12) 3.347(13) 126(12) .
N1 H1 Cl12 0.89(2) 2.83(13) 3.387(13) 122(12) .
N1 H1 Cl15 0.89(2) 2.96(10) 3.679(14) 140(12) .
N2 H2 Cl2 0.89(2) 2.56(9) 3.307(13) 142(12) 4_456
N3 H3 Cl10 0.89(2) 2.51(5) 3.364(13) 161(13) .
N4 H4 Cl7 0.89(2) 2.53(7) 3.340(13) 152(13) 4_566
N5 H5 Cl4 0.89(2) 2.52(9) 3.312(15) 148(14) 3_655
N6 H6 Cl4 0.89(2) 2.74(10) 3.466(15) 140(13) .
N6 H6 Cl15 0.89(2) 2.89(11) 3.601(14) 138(13) .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         2.483
_refine_diff_density_min         -1.670
_refine_diff_density_rms         0.271
####################################################################### 
# 
# 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_3c
_database_code_depnum_ccdc_archive 'CCDC 1473393'
_audit_update_record             
;
2016-04-11 deposited with the CCDC.
2016-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H12 Cl5 N2 O W'
_chemical_formula_weight         477.27

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'
W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   9.1938(18)
_cell_length_b                   14.574(3)
_cell_length_c                   9.857(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.519(2)
_cell_angle_gamma                90.00
_cell_volume                     1312.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3310
_cell_measurement_theta_min      2.5055
_cell_measurement_theta_max      27.6515

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             892
_exptl_absorpt_coefficient_mu    9.793
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.2219
_exptl_absorpt_correction_T_max  0.3625
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1738 (selected reflections only, before parameter refinement)
 R(int) =  0.0595 (selected reflections only, after parameter refinement)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '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            10541
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.51
_diffrn_reflns_theta_max         27.00
_reflns_number_total             2858
_reflns_number_gt                2467
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1996)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

_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)+(0.0218P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2858
_refine_ls_number_parameters     131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0653
_refine_ls_wR_factor_gt          0.0630
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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
C1 C 0.7857(5) 0.0772(3) 0.2909(5) 0.0164(10) Uani 1 1 d . . .
C2 C 0.9245(6) -0.0468(3) 0.1997(6) 0.0197(11) Uani 1 1 d . . .
H2A H 0.9773 -0.0393 0.1194 0.030 Uiso 1 1 calc R . .
H2B H 0.8883 -0.1099 0.2030 0.030 Uiso 1 1 calc R . .
H2C H 0.9908 -0.0340 0.2825 0.030 Uiso 1 1 calc R . .
C3 C 0.6951(6) 0.0082(4) 0.0694(5) 0.0225(12) Uani 1 1 d . . .
H3A H 0.7461 0.0134 -0.0123 0.034 Uiso 1 1 calc R . .
H3B H 0.6214 0.0568 0.0688 0.034 Uiso 1 1 calc R . .
H3C H 0.6471 -0.0518 0.0702 0.034 Uiso 1 1 calc R . .
C4 C 0.5262(6) 0.0493(4) 0.2997(6) 0.0244(12) Uani 1 1 d . . .
H4A H 0.4727 0.0494 0.3803 0.037 Uiso 1 1 calc R . .
H4B H 0.5524 -0.0138 0.2785 0.037 Uiso 1 1 calc R . .
H4C H 0.4642 0.0755 0.2218 0.037 Uiso 1 1 calc R . .
C5 C 0.6491(6) 0.1799(3) 0.4241(6) 0.0236(12) Uani 1 1 d . . .
H5A H 0.5562 0.2124 0.4015 0.035 Uiso 1 1 calc R . .
H5B H 0.7306 0.2225 0.4182 0.035 Uiso 1 1 calc R . .
H5C H 0.6538 0.1554 0.5170 0.035 Uiso 1 1 calc R . .
Cl1 Cl 1.26181(16) 0.29312(9) 0.36598(16) 0.0290(3) Uani 1 1 d . . .
Cl2 Cl 1.21023(14) 0.07799(9) 0.47783(13) 0.0229(3) Uani 1 1 d . . .
Cl3 Cl 1.12731(15) 0.13751(9) 0.15464(13) 0.0235(3) Uani 1 1 d . . .
Cl4 Cl 0.90930(16) 0.29674(9) 0.24193(14) 0.0268(3) Uani 1 1 d . . .
Cl5 Cl 1.01259(15) 0.25387(9) 0.57050(13) 0.0235(3) Uani 1 1 d . . .
N1 N 0.8002(4) 0.0174(3) 0.1908(4) 0.0185(9) Uani 1 1 d . . .
N2 N 0.6590(5) 0.1042(3) 0.3274(4) 0.0181(9) Uani 1 1 d . . .
O1 O 0.9057(4) 0.1098(2) 0.3603(3) 0.0173(8) Uani 1 1 d . . .
W1 W 1.06985(2) 0.193676(13) 0.36386(2) 0.01527(8) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.317(6) . ?
C1 O1 1.319(6) . ?
C1 N1 1.335(7) . ?
C2 N1 1.472(6) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 N1 1.456(6) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 N2 1.459(6) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 N2 1.468(6) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
Cl1 W1 2.2819(14) . ?
Cl2 W1 2.3327(13) . ?
Cl3 W1 2.3344(14) . ?
Cl4 W1 2.3403(13) . ?
Cl5 W1 2.3323(14) . ?
O1 W1 1.939(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 C1 O1 117.7(4) . . ?
N2 C1 N1 124.2(4) . . ?
O1 C1 N1 118.1(4) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 N1 C3 123.7(4) . . ?
C1 N1 C2 120.9(4) . . ?
C3 N1 C2 115.4(4) . . ?
C1 N2 C4 122.2(4) . . ?
C1 N2 C5 121.6(4) . . ?
C4 N2 C5 114.9(4) . . ?
C1 O1 W1 147.1(3) . . ?
O1 W1 Cl1 179.38(11) . . ?
O1 W1 Cl5 90.01(11) . . ?
Cl1 W1 Cl5 90.24(5) . . ?
O1 W1 Cl2 86.57(10) . . ?
Cl1 W1 Cl2 93.99(5) . . ?
Cl5 W1 Cl2 91.07(5) . . ?
O1 W1 Cl3 90.97(11) . . ?
Cl1 W1 Cl3 88.77(5) . . ?
Cl5 W1 Cl3 178.43(5) . . ?
Cl2 W1 Cl3 90.21(5) . . ?
O1 W1 Cl4 87.19(10) . . ?
Cl1 W1 Cl4 92.24(5) . . ?
Cl5 W1 Cl4 90.88(5) . . ?
Cl2 W1 Cl4 173.46(5) . . ?
Cl3 W1 Cl4 87.95(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C1 N1 C3 31.8(8) . . . . ?
O1 C1 N1 C3 -150.1(5) . . . . ?
N2 C1 N1 C2 -146.1(5) . . . . ?
O1 C1 N1 C2 32.0(7) . . . . ?
O1 C1 N2 C4 -155.1(4) . . . . ?
N1 C1 N2 C4 23.0(8) . . . . ?
O1 C1 N2 C5 11.0(7) . . . . ?
N1 C1 N2 C5 -170.8(5) . . . . ?
N2 C1 O1 W1 -105.4(6) . . . . ?
N1 C1 O1 W1 76.3(7) . . . . ?
C1 O1 W1 Cl1 14(11) . . . . ?
C1 O1 W1 Cl5 127.4(6) . . . . ?
C1 O1 W1 Cl2 -141.5(6) . . . . ?
C1 O1 W1 Cl3 -51.4(6) . . . . ?
C1 O1 W1 Cl4 36.5(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.428
_refine_diff_density_min         -0.763
_refine_diff_density_rms         0.179

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1478899'
_audit_update_record             
;
2016-05-09 deposited with the CCDC.
2016-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H21 Cl4 N2 O2 W'
_chemical_formula_weight         514.93

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'
W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   9.7817(6)
_cell_length_b                   12.5746(7)
_cell_length_c                   13.7251(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.9790(10)
_cell_angle_gamma                90.00
_cell_volume                     1687.19(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7565
_cell_measurement_theta_min      2.197
_cell_measurement_theta_max      28.7185

_exptl_crystal_description       plate
_exptl_crystal_colour            bright-green
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.027
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             988
_exptl_absorpt_coefficient_mu    7.476
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.2901
_exptl_absorpt_correction_T_max  0.4674
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1341 (selected reflections only, before parameter refinement)
 R(int) =  0.0483 (selected reflections only, after parameter refinement)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '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            19303
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         28.00
_reflns_number_total             4024
_reflns_number_gt                3525
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1996)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

_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)+(0.0162P)²+0.4640P] 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         4024
_refine_ls_number_parameters     163
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0203
_refine_ls_wR_factor_ref         0.0433
_refine_ls_wR_factor_gt          0.0413
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.092
_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
W1 W 1.081647(12) 0.186494(10) 0.189936(8) 0.01445(4) Uani 1 1 d . . .
Cl1 Cl 1.13960(8) 0.20259(6) 0.02388(5) 0.02129(17) Uani 1 1 d . . .
Cl2 Cl 0.98475(9) 0.01827(6) 0.15579(6) 0.02379(17) Uani 1 1 d . . .
Cl3 Cl 0.98518(8) 0.17998(6) 0.34924(5) 0.01903(16) Uani 1 1 d . . .
Cl4 Cl 1.09813(8) 0.37305(6) 0.20717(6) 0.02397(18) Uani 1 1 d . . .
O1 O 1.2396(2) 0.15014(19) 0.22888(16) 0.0233(5) Uani 1 1 d . . .
O2 O 0.8653(2) 0.23489(17) 0.13812(15) 0.0181(5) Uani 1 1 d . . .
N1 N 0.7423(3) 0.2535(2) -0.00677(18) 0.0171(6) Uani 1 1 d . . .
H1 H 0.6526 0.2707 -0.0252 0.021 Uiso 1 1 calc RD . .
N2 N 0.6357(2) 0.2499(2) 0.14863(17) 0.0149(5) Uani 1 1 d . . .
C1 C 0.7504(3) 0.2446(2) 0.1019(2) 0.0143(6) Uani 1 1 d . . .
C2 C 0.8334(3) 0.3430(3) -0.0401(2) 0.0231(7) Uani 1 1 d . . .
H2A H 0.9303 0.3226 -0.0280 0.028 Uiso 1 1 calc R . .
H2B H 0.8186 0.3533 -0.1112 0.028 Uiso 1 1 calc R . .
C3 C 0.8068(4) 0.4449(3) 0.0106(3) 0.0314(8) Uani 1 1 d . . .
H3A H 0.8681 0.4999 -0.0133 0.047 Uiso 1 1 calc R . .
H3B H 0.8232 0.4356 0.0809 0.047 Uiso 1 1 calc R . .
H3C H 0.7116 0.4663 -0.0023 0.047 Uiso 1 1 calc R . .
C4 C 0.7763(3) 0.1479(3) -0.0540(2) 0.0236(7) Uani 1 1 d . . .
H4A H 0.7786 0.1577 -0.1254 0.028 Uiso 1 1 calc R . .
H4B H 0.8686 0.1250 -0.0306 0.028 Uiso 1 1 calc R . .
C5 C 0.6750(4) 0.0620(3) -0.0319(3) 0.0302(8) Uani 1 1 d . . .
H5A H 0.7016 -0.0042 -0.0638 0.045 Uiso 1 1 calc R . .
H5B H 0.5837 0.0834 -0.0564 0.045 Uiso 1 1 calc R . .
H5C H 0.6735 0.0509 0.0387 0.045 Uiso 1 1 calc R . .
C6 C 0.4937(3) 0.2565(3) 0.1056(2) 0.0189(7) Uani 1 1 d . . .
H6A H 0.4319 0.2128 0.1447 0.023 Uiso 1 1 calc R . .
H6B H 0.4922 0.2273 0.0385 0.023 Uiso 1 1 calc RD . .
C7 C 0.4423(3) 0.3703(3) 0.1026(2) 0.0239(7) Uani 1 1 d . . .
H7A H 0.3495 0.3720 0.0733 0.036 Uiso 1 1 calc R . .
H7B H 0.5030 0.4137 0.0635 0.036 Uiso 1 1 calc R . .
H7C H 0.4412 0.3987 0.1690 0.036 Uiso 1 1 calc R . .
C8 C 0.6454(3) 0.2430(3) 0.2565(2) 0.0196(7) Uani 1 1 d . . .
H8A H 0.5720 0.2864 0.2844 0.024 Uiso 1 1 calc R . .
H8B H 0.7344 0.2723 0.2802 0.024 Uiso 1 1 calc R . .
C9 C 0.6325(4) 0.1293(3) 0.2909(2) 0.0257(8) Uani 1 1 d . . .
H9A H 0.6391 0.1272 0.3623 0.039 Uiso 1 1 calc R . .
H9B H 0.7061 0.0864 0.2643 0.039 Uiso 1 1 calc R . .
H9C H 0.5438 0.1005 0.2683 0.039 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
W1 O1 1.681(2) . ?
W1 O2 2.292(2) . ?
W1 Cl2 2.3584(8) . ?
W1 Cl4 2.3627(8) . ?
W1 Cl1 2.3761(8) . ?
W1 Cl3 2.4126(7) . ?
O2 C1 1.219(3) . ?
N1 C1 1.495(4) . ?
N1 C2 1.515(4) . ?
N1 C4 1.520(4) . ?
N1 H1 0.9300 . ?
N2 C1 1.313(4) . ?
N2 C8 1.483(4) . ?
N2 C6 1.493(4) . ?
C2 C3 1.485(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.503(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.516(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.512(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 W1 O2 179.37(9) . . ?
O1 W1 Cl2 100.25(8) . . ?
O2 W1 Cl2 79.40(6) . . ?
O1 W1 Cl4 100.33(9) . . ?
O2 W1 Cl4 80.01(6) . . ?
Cl2 W1 Cl4 159.39(3) . . ?
O1 W1 Cl1 94.65(7) . . ?
O2 W1 Cl1 85.87(6) . . ?
Cl2 W1 Cl1 89.62(3) . . ?
Cl4 W1 Cl1 89.64(3) . . ?
O1 W1 Cl3 94.97(7) . . ?
O2 W1 Cl3 84.51(6) . . ?
Cl2 W1 Cl3 89.00(3) . . ?
Cl4 W1 Cl3 88.31(3) . . ?
Cl1 W1 Cl3 170.38(3) . . ?
C1 O2 W1 169.0(2) . . ?
C1 N1 C2 110.2(2) . . ?
C1 N1 C4 110.8(2) . . ?
C2 N1 C4 112.4(2) . . ?
C1 N1 H1 107.8 . . ?
C2 N1 H1 107.8 . . ?
C4 N1 H1 107.8 . . ?
C1 N2 C8 117.3(2) . . ?
C1 N2 C6 127.5(3) . . ?
C8 N2 C6 115.1(2) . . ?
O2 C1 N2 126.6(3) . . ?
O2 C1 N1 115.6(3) . . ?
N2 C1 N1 117.8(3) . . ?
C3 C2 N1 112.6(3) . . ?
C3 C2 H2A 109.1 . . ?
N1 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
N1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 N1 112.7(3) . . ?
C5 C4 H4A 109.0 . . ?
N1 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
N1 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 C7 111.5(3) . . ?
N2 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
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 111.3(3) . . ?
N2 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N2 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 W1 O2 C1 -82(10) . . . . ?
Cl2 W1 O2 C1 -26.1(11) . . . . ?
Cl4 W1 O2 C1 154.7(11) . . . . ?
Cl1 W1 O2 C1 64.3(11) . . . . ?
Cl3 W1 O2 C1 -116.1(11) . . . . ?
W1 O2 C1 N2 117.9(10) . . . . ?
W1 O2 C1 N1 -63.4(12) . . . . ?
C8 N2 C1 O2 -0.2(5) . . . . ?
C6 N2 C1 O2 -176.8(3) . . . . ?
C8 N2 C1 N1 -178.9(2) . . . . ?
C6 N2 C1 N1 4.6(4) . . . . ?
C2 N1 C1 O2 -54.3(3) . . . . ?
C4 N1 C1 O2 70.7(3) . . . . ?
C2 N1 C1 N2 124.5(3) . . . . ?
C4 N1 C1 N2 -110.5(3) . . . . ?
C1 N1 C2 C3 -52.2(3) . . . . ?
C4 N1 C2 C3 -176.2(3) . . . . ?
C1 N1 C4 C5 64.0(3) . . . . ?
C2 N1 C4 C5 -172.3(3) . . . . ?
C1 N2 C6 C7 -97.8(3) . . . . ?
C8 N2 C6 C7 85.7(3) . . . . ?
C1 N2 C8 C9 -91.4(3) . . . . ?
C6 N2 C8 C9 85.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 Cl3 0.93 2.42 3.254(3) 149.6 4_565

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.922
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.115
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1478900'
_audit_update_record             
;
2016-05-09 deposited with the CCDC.
2016-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H8 Cl4 N2 O2 W'
_chemical_formula_weight         429.76

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'
W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   9.483(2)
_cell_length_b                   10.127(2)
_cell_length_c                   11.202(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 89.971(2)
_cell_angle_gamma                90.00
_cell_volume                     1075.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7743
_cell_measurement_theta_min      2.7115
_cell_measurement_theta_max      27.450

_exptl_crystal_description       prism
_exptl_crystal_colour            red-orange
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.654
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    11.696
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.2562
_exptl_absorpt_correction_T_max  0.3876
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1562 (selected reflections only, before parameter refinement)
 R(int) =  0.0772 (selected reflections only, after parameter refinement)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  '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            9529
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_sigmaI/netI    0.0427
_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       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         25.49
_reflns_number_total             1975
_reflns_number_gt                1842
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1996)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

_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. The following restraints
 were applied (given as SHELXL lines): 
 dfix 1.25 c1 o2
 dfix 1.33 c1 n1 c1 n2
 dfix 1.45 n1 c2 n2 c3
 simu .01 c1 > w1
 isor .01  $o $n $c cl3 cl4
 isor .005 cl1 cl2
;

_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)+(0.0399P)²+48.6062P] 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         1975
_refine_ls_number_parameters     110
_refine_ls_number_restraints     107
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1470
_refine_ls_wR_factor_gt          0.1436
_refine_ls_goodness_of_fit_ref   1.225
_refine_ls_restrained_S_all      1.258
_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
C1 C 0.5303(18) 0.669(2) 0.9540(16) 0.029(3) Uani 1 1 d DU . .
C2 C 0.7726(18) 0.762(2) 0.987(3) 0.041(5) Uani 1 1 d DU . .
H2A H 0.8138 0.8211 1.0472 0.061 Uiso 1 1 calc R . .
H2B H 0.7832 0.8014 0.9078 0.061 Uiso 1 1 calc R . .
H2C H 0.8210 0.6767 0.9894 0.061 Uiso 1 1 calc R . .
C3 C 0.496(3) 0.522(2) 0.7762(16) 0.028(5) Uani 1 1 d DU . .
H3A H 0.5551 0.4913 0.7101 0.042 Uiso 1 1 calc R . .
H3B H 0.4172 0.5740 0.7446 0.042 Uiso 1 1 calc R . .
H3C H 0.4593 0.4460 0.8204 0.042 Uiso 1 1 calc R . .
Cl1 Cl 0.3465(12) 0.9035(9) 1.1372(8) 0.051(2) Uani 1 1 d U . .
Cl2 Cl 0.3436(13) 0.8815(9) 0.8456(8) 0.054(2) Uani 1 1 d U . .
Cl3 Cl 0.1380(16) 0.6434(12) 0.8531(10) 0.076(3) Uani 1 1 d U . .
Cl4 Cl 0.1384(11) 0.6259(9) 1.1390(8) 0.055(2) Uani 1 1 d U . .
N1 N 0.6241(15) 0.7431(16) 1.013(2) 0.036(4) Uani 1 1 d DU . .
H1 H 0.5913 0.7861 1.0753 0.043 Uiso 1 1 calc R . .
N2 N 0.5804(18) 0.6048(16) 0.8565(14) 0.027(3) Uani 1 1 d DU . .
H2 H 0.6707 0.6137 0.8401 0.032 Uiso 1 1 calc R . .
O1 O 0.0865(12) 0.8812(11) 0.994(2) 0.027(3) Uani 1 1 d U . .
O2 O 0.4060(12) 0.6539(12) 1.0110(19) 0.029(3) Uani 1 1 d DU . .
W1 W 0.22424(6) 0.77501(6) 0.99951(14) 0.0216(3) Uani 1 1 d U . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.341(17) . ?
C1 O2 1.349(16) . ?
C1 N2 1.354(16) . ?
C2 N1 1.450(17) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 N2 1.466(18) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
Cl1 W1 2.327(9) . ?
Cl2 W1 2.327(8) . ?
Cl3 W1 2.266(10) . ?
Cl4 W1 2.320(8) . ?
N1 H1 0.8800 . ?
N2 H2 0.8800 . ?
O1 W1 1.693(11) . ?
O2 W1 2.119(11) . ?

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 C1 O2 114.1(15) . . ?
N1 C1 N2 115.7(17) . . ?
O2 C1 N2 129.5(18) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 N1 C2 128(2) . . ?
C1 N1 H1 115.8 . . ?
C2 N1 H1 115.8 . . ?
C1 N2 C3 125.1(18) . . ?
C1 N2 H2 117.4 . . ?
C3 N2 H2 117.4 . . ?
C1 O2 W1 128.2(13) . . ?
O1 W1 O2 175.8(6) . . ?
O1 W1 Cl3 93.8(7) . . ?
O2 W1 Cl3 89.9(6) . . ?
O1 W1 Cl4 99.8(6) . . ?
O2 W1 Cl4 82.4(5) . . ?
Cl3 W1 Cl4 88.7(3) . . ?
O1 W1 Cl1 93.2(7) . . ?
O2 W1 Cl1 83.0(5) . . ?
Cl3 W1 Cl1 171.2(4) . . ?
Cl4 W1 Cl1 95.3(4) . . ?
O1 W1 Cl2 92.9(7) . . ?
O2 W1 Cl2 85.3(5) . . ?
Cl3 W1 Cl2 85.0(4) . . ?
Cl4 W1 Cl2 166.2(3) . . ?
Cl1 W1 Cl2 89.4(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 N1 C2 170(2) . . . . ?
N2 C1 N1 C2 -1(4) . . . . ?
N1 C1 N2 C3 -178(2) . . . . ?
O2 C1 N2 C3 13(4) . . . . ?
N1 C1 O2 W1 89(2) . . . . ?
N2 C1 O2 W1 -101(3) . . . . ?
C1 O2 W1 O1 -58(13) . . . . ?
C1 O2 W1 Cl3 92.8(18) . . . . ?
C1 O2 W1 Cl4 -178.4(18) . . . . ?
C1 O2 W1 Cl1 -82.1(17) . . . . ?
C1 O2 W1 Cl2 7.9(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 Cl1 0.88 2.70 3.39(2) 136.6 .
N2 H2 Cl1 0.88 2.82 3.522(19) 137.4 4_675

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         4.439
_refine_diff_density_min         -2.745
_refine_diff_density_rms         0.386
