# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_p21c
_database_code_depnum_ccdc_archive 'CCDC 1016460'
_audit_update_record             
;
2014-07-28 deposited with the CCDC.
2014-11-27 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 Cl6 N2 O W'
_chemical_formula_weight         569.83

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                   11.225(2)
_cell_length_b                   10.379(2)
_cell_length_c                   16.136(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.590(2)
_cell_angle_gamma                90.00
_cell_volume                     1879.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5649
_cell_measurement_theta_min      2.5295
_cell_measurement_theta_max      28.5405

_exptl_crystal_description       plate
_exptl_crystal_colour            pale-orange
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.014
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1092
_exptl_absorpt_coefficient_mu    6.992
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.4008
_exptl_absorpt_correction_T_max  0.4875
_exptl_absorpt_process_details   
;
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption corrections SADABS).
 R(int) = 0.1691 (selected reflections only, before parameter refinement)
 R(int) = 0.0518 (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            13524
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         25.68
_reflns_number_total             3560
_reflns_number_gt                3094
_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 0.93 n2 h2
;

_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)+(0.0281P)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         3560
_refine_ls_number_parameters     179
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0583
_refine_ls_wR_factor_gt          0.0559
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3317(3) 0.8145(3) 0.2727(2) 0.0202(8) Uani 1 1 d . . .
C2 C 0.4965(3) 0.6916(4) 0.2266(2) 0.0234(8) Uani 1 1 d . . .
H2A H 0.5385 0.6148 0.2487 0.028 Uiso 1 1 calc R . .
H2B H 0.5422 0.7689 0.2437 0.028 Uiso 1 1 calc R . .
C3 C 0.4920(3) 0.6843(4) 0.1327(2) 0.0318(9) Uani 1 1 d . . .
H3A H 0.4473 0.6076 0.1156 0.048 Uiso 1 1 calc R . .
H3B H 0.5733 0.6793 0.1113 0.048 Uiso 1 1 calc R . .
H3C H 0.4527 0.7615 0.1106 0.048 Uiso 1 1 calc R . .
C4 C 0.3187(3) 0.5732(3) 0.2808(2) 0.0271(9) Uani 1 1 d . . .
H4A H 0.3381 0.5108 0.2365 0.033 Uiso 1 1 calc R . .
H4B H 0.2311 0.5846 0.2810 0.033 Uiso 1 1 calc R . .
C5 C 0.3587(4) 0.5189(4) 0.3635(3) 0.0396(10) Uani 1 1 d . . .
H5A H 0.4457 0.5106 0.3644 0.059 Uiso 1 1 calc R . .
H5B H 0.3225 0.4339 0.3716 0.059 Uiso 1 1 calc R . .
H5C H 0.3338 0.5769 0.4080 0.059 Uiso 1 1 calc R . .
C6 C 0.2144(3) 0.9137(4) 0.3845(2) 0.0270(9) Uani 1 1 d . . .
H6A H 0.2480 0.9976 0.3674 0.032 Uiso 1 1 calc R . .
H6B H 0.1329 0.9290 0.4053 0.032 Uiso 1 1 calc R . .
C7 C 0.2904(3) 0.8574(4) 0.4531(2) 0.0374(11) Uani 1 1 d . . .
H7A H 0.2540 0.7774 0.4729 0.056 Uiso 1 1 calc R . .
H7B H 0.2962 0.9192 0.4989 0.056 Uiso 1 1 calc R . .
H7C H 0.3702 0.8391 0.4321 0.056 Uiso 1 1 calc R . .
C8 C 0.1213(3) 0.8761(4) 0.2453(2) 0.0246(8) Uani 1 1 d . . .
H8A H 0.0425 0.8892 0.2710 0.029 Uiso 1 1 calc R . .
H8B H 0.1498 0.9607 0.2254 0.029 Uiso 1 1 calc R . .
C9 C 0.1075(3) 0.7856(4) 0.1721(3) 0.0300(9) Uani 1 1 d . . .
H9A H 0.1860 0.7675 0.1487 0.045 Uiso 1 1 calc R . .
H9B H 0.0566 0.8258 0.1298 0.045 Uiso 1 1 calc R . .
H9C H 0.0710 0.7048 0.1905 0.045 Uiso 1 1 calc R . .
Cl1 Cl 0.89143(7) 0.95212(8) 0.40366(6) 0.0247(2) Uani 1 1 d . . .
Cl2 Cl 0.73103(8) 0.54119(9) 0.42161(6) 0.0292(2) Uani 1 1 d . . .
Cl3 Cl 0.62218(7) 0.83104(10) 0.41594(6) 0.0277(2) Uani 1 1 d . . .
Cl4 Cl 0.80639(9) 0.73858(8) 0.26824(6) 0.0248(2) Uani 1 1 d . . .
Cl5 Cl 1.00668(7) 0.65050(9) 0.40546(6) 0.0260(2) Uani 1 1 d . . .
Cl6 Cl 0.83347(9) 0.75790(8) 0.55364(6) 0.0256(2) Uani 1 1 d . . .
N1 N 0.3757(2) 0.6979(3) 0.26229(18) 0.0180(6) Uani 1 1 d . . .
N2 N 0.2082(2) 0.8247(3) 0.31040(18) 0.0196(6) Uani 1 1 d D . .
H2 H 0.182(3) 0.749(2) 0.331(2) 0.024 Uiso 1 1 d D . .
O1 O 0.3779(2) 0.9163(2) 0.25516(16) 0.0273(6) Uani 1 1 d . . .
W1 W 0.812495(12) 0.743338(13) 0.412126(8) 0.01789(7) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0197(18) 0.020(2) 0.0209(19) -0.0022(16) 0.0010(14) -0.0001(15)
C2 0.0166(18) 0.024(2) 0.029(2) -0.0003(17) 0.0037(15) 0.0028(15)
C3 0.035(2) 0.034(2) 0.027(2) -0.0040(19) 0.0099(18) -0.0037(18)
C4 0.033(2) 0.0150(19) 0.034(2) -0.0004(16) 0.0062(17) -0.0052(16)
C5 0.058(3) 0.023(2) 0.039(3) 0.0082(19) 0.013(2) -0.001(2)
C6 0.0189(18) 0.032(2) 0.031(2) -0.0132(18) 0.0029(16) 0.0005(15)
C7 0.026(2) 0.053(3) 0.033(2) -0.018(2) -0.0007(17) 0.001(2)
C8 0.0185(18) 0.026(2) 0.029(2) 0.0005(17) 0.0002(15) 0.0010(15)
C9 0.024(2) 0.036(2) 0.030(2) -0.0007(19) -0.0017(17) 0.0010(17)
Cl1 0.0245(4) 0.0189(5) 0.0308(5) -0.0001(4) 0.0079(4) 0.0006(3)
Cl2 0.0345(5) 0.0281(5) 0.0252(5) -0.0023(4) 0.0073(4) -0.0091(4)
Cl3 0.0190(4) 0.0387(6) 0.0255(5) -0.0007(4) 0.0025(4) 0.0037(4)
Cl4 0.0276(5) 0.0313(5) 0.0157(5) 0.0001(4) 0.0034(4) -0.0002(4)
Cl5 0.0225(4) 0.0237(5) 0.0319(5) 0.0049(4) 0.0054(4) 0.0042(4)
Cl6 0.0289(5) 0.0315(6) 0.0163(5) -0.0009(4) -0.0003(4) -0.0002(4)
N1 0.0199(15) 0.0137(15) 0.0204(16) -0.0005(13) 0.0032(12) -0.0006(12)
N2 0.0198(15) 0.0174(17) 0.0218(16) -0.0040(13) 0.0021(12) -0.0010(12)
O1 0.0239(13) 0.0149(14) 0.0432(17) 0.0029(12) 0.0077(12) -0.0005(11)
W1 0.01813(10) 0.02030(10) 0.01529(10) -0.00005(6) 0.00281(6) -0.00047(6)

_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 1.212(4) . ?
C1 N1 1.319(5) . ?
C1 N2 1.523(4) . ?
C2 N1 1.480(4) . ?
C2 C3 1.517(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 N1 1.476(4) . ?
C4 C5 1.513(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.508(5) . ?
C6 N2 1.512(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.515(5) . ?
C8 N2 1.523(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
Cl1 W1 2.3455(10) . ?
Cl2 W1 2.2944(10) . ?
Cl3 W1 2.3235(9) . ?
Cl4 W1 2.3225(11) . ?
Cl5 W1 2.3865(9) . ?
Cl6 W1 2.2980(11) . ?
N2 H2 0.898(18) . ?

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 127.5(3) . . ?
O1 C1 N2 115.2(3) . . ?
N1 C1 N2 117.3(3) . . ?
N1 C2 C3 111.7(3) . . ?
N1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
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 . . ?
N1 C4 C5 112.3(3) . . ?
N1 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
N1 C4 H4B 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.9 . . ?
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 . . ?
C7 C6 N2 111.4(3) . . ?
C7 C6 H6A 109.3 . . ?
N2 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
N2 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 . . ?
C9 C8 N2 112.3(3) . . ?
C9 C8 H8A 109.1 . . ?
N2 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
N2 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
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 . . ?
C1 N1 C4 128.0(3) . . ?
C1 N1 C2 115.8(3) . . ?
C4 N1 C2 116.2(3) . . ?
C6 N2 C8 110.9(3) . . ?
C6 N2 C1 108.9(3) . . ?
C8 N2 C1 109.2(3) . . ?
C6 N2 H2 105(2) . . ?
C8 N2 H2 110(2) . . ?
C1 N2 H2 113(2) . . ?
Cl2 W1 Cl6 91.76(3) . . ?
Cl2 W1 Cl4 92.27(3) . . ?
Cl6 W1 Cl4 175.09(3) . . ?
Cl2 W1 Cl3 89.39(4) . . ?
Cl6 W1 Cl3 91.88(3) . . ?
Cl4 W1 Cl3 90.98(3) . . ?
Cl2 W1 Cl1 178.60(3) . . ?
Cl6 W1 Cl1 87.83(3) . . ?
Cl4 W1 Cl1 88.21(3) . . ?
Cl3 W1 Cl1 89.29(3) . . ?
Cl2 W1 Cl5 89.92(4) . . ?
Cl6 W1 Cl5 89.26(3) . . ?
Cl4 W1 Cl5 87.93(3) . . ?
Cl3 W1 Cl5 178.69(3) . . ?
Cl1 W1 Cl5 91.41(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
O1 C1 N1 C4 -177.8(4) . . . . ?
N2 C1 N1 C4 1.7(5) . . . . ?
O1 C1 N1 C2 1.3(5) . . . . ?
N2 C1 N1 C2 -179.2(3) . . . . ?
C5 C4 N1 C1 -98.2(4) . . . . ?
C5 C4 N1 C2 82.7(4) . . . . ?
C3 C2 N1 C1 -90.2(4) . . . . ?
C3 C2 N1 C4 89.0(4) . . . . ?
C7 C6 N2 C8 174.2(3) . . . . ?
C7 C6 N2 C1 -65.7(4) . . . . ?
C9 C8 N2 C6 -176.8(3) . . . . ?
C9 C8 N2 C1 63.3(4) . . . . ?
O1 C1 N2 C6 -54.1(4) . . . . ?
N1 C1 N2 C6 126.4(3) . . . . ?
O1 C1 N2 C8 67.1(4) . . . . ?
N1 C1 N2 C8 -112.5(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
N2 H2 Cl5 0.898(18) 2.53(3) 3.288(3) 142(3) 1_455

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.391
_refine_diff_density_min         -1.257
_refine_diff_density_rms         0.117
