# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_014ZRT17
_audit_block_doi                 10.5517/ccdc.csd.cc1nsmfh
_database_code_depnum_ccdc_archive 'CCDC 1543007'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7QI00128B 2017
_audit_update_record             
;
2017-04-08 deposited with the CCDC.
2017-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H18 Cl N W'
_chemical_formula_sum            'C11 H18 Cl N W'
_chemical_formula_weight         383.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
W W -5.4734 5.5774 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

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

_cell_length_a                   21.1055(3)
_cell_length_b                   7.25260(10)
_cell_length_c                   17.4808(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2675.78(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6150
_cell_measurement_theta_min      4.1420
_cell_measurement_theta_max      76.1180

_exptl_crystal_description       irregular
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.904
_exptl_crystal_F_000             1456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.302
_exptl_crystal_size_mid          0.229
_exptl_crystal_size_min          0.146
_exptl_absorpt_coefficient_mu    17.554
_shelx_estimated_absorpt_T_min   0.076
_shelx_estimated_absorpt_T_max   0.184
_exptl_absorpt_correction_T_min  0.10639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150.0(5)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.4102
_diffrn_reflns_number            8777
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.189
_diffrn_reflns_theta_max         74.477
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2949
_reflns_number_gt                2795
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    
;
SIR-92 
Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A. 
J. Appl. Cryst. 1994, 27, 435.
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
ORTEP3 for Windows. Farrugia, L. J. J. Appl. Cryst. 1997, 30, 565.
;
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0796P)²+7.3986P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00022(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2949
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1220
_refine_ls_wR_factor_gt          0.1187
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4115(4) 0.0019(9) 0.0590(5) 0.0378(17) Uani 1 1 d . . . . .
H1A H 0.4159 0.0260 0.0041 0.057 Uiso 1 1 calc R U . . .
H1B H 0.3765 -0.0846 0.0675 0.057 Uiso 1 1 calc R U . . .
H1C H 0.4509 -0.0517 0.0787 0.057 Uiso 1 1 calc R U . . .
C4 C 0.5280(4) 0.2500 0.1881(5) 0.0281(11) Uani 1 2 d S T P . .
C5 C 0.5798(5) 0.2500 0.1394(5) 0.0266(19) Uani 1 2 d S T P . .
H5 H 0.5731 0.2500 0.0857 0.032 Uiso 1 2 calc R U P . .
C6 C 0.6414(5) 0.2500 0.1674(6) 0.0281(11) Uani 1 2 d S T P . .
C7 C 0.6498(5) 0.2500 0.2462(6) 0.034(2) Uani 1 2 d S T P . .
H7 H 0.6915 0.2500 0.2664 0.041 Uiso 1 2 calc R U P . .
C8 C 0.5983(4) 0.2500 0.2966(6) 0.0281(11) Uani 1 2 d S T P . .
C9 C 0.5370(4) 0.2500 0.2674(5) 0.0257(18) Uani 1 2 d S T P . .
H9 H 0.5016 0.2500 0.3009 0.031 Uiso 1 2 calc R U P . .
C10 C 0.6982(6) 0.2500 0.1132(7) 0.048(3) Uani 1 2 d S T P . .
H10A H 0.6832 0.2500 0.0602 0.072 Uiso 1 2 calc R U P . .
H10B H 0.7239 0.3603 0.1224 0.072 Uiso 0.5 1 calc R U P . .
H10C H 0.7239 0.1397 0.1224 0.072 Uiso 0.5 1 calc R U P . .
C11 C 0.6099(6) 0.2500 0.3820(7) 0.059(4) Uani 1 2 d S T P . .
H11A H 0.6556 0.2500 0.3919 0.088 Uiso 1 2 calc R U P . .
H11B H 0.5908 0.3603 0.4047 0.088 Uiso 0.5 1 calc R U P . .
H11C H 0.5908 0.1397 0.4047 0.088 Uiso 0.5 1 calc R U P . .
C2 C 0.3421(5) 0.2500 0.2203(6) 0.035(2) Uani 1 2 d S T P . .
H2A H 0.2965 0.2500 0.2096 0.052 Uiso 1 2 calc R U P . .
H2B H 0.3531 0.1397 0.2498 0.052 Uiso 0.5 1 calc R U P . .
H2C H 0.3531 0.3603 0.2498 0.052 Uiso 0.5 1 calc R U P . .
C12 C 0.4632(5) -0.2500 0.2589(5) 0.038(2) Uani 1 2 d S T P . .
H12A H 0.5085 -0.2500 0.2711 0.057 Uiso 1 2 calc R U P . .
H12B H 0.4528 -0.3603 0.2291 0.057 Uiso 0.5 1 calc R U P . .
H12C H 0.4528 -0.1397 0.2291 0.057 Uiso 0.5 1 calc R U P . .
N1 N 0.4667(4) 0.2500 0.1589(4) 0.0254(15) Uani 1 2 d S T P . .
Cl1 Cl 0.29239(12) 0.2500 0.05110(17) 0.0477(6) Uani 1 2 d S T P . .
W1 W 0.39259(2) 0.2500 0.11653(2) 0.02086(17) Uani 1 2 d S T P . .
C13 C 0.3909(4) -0.0032(10) 0.4174(5) 0.0420(18) Uani 1 1 d . . . . .
H13A H 0.3496 0.0437 0.4009 0.063 Uiso 1 1 calc R U . . .
H13B H 0.4239 0.0873 0.4050 0.063 Uiso 1 1 calc R U . . .
H13C H 0.3903 -0.0243 0.4728 0.063 Uiso 1 1 calc R U . . .
C15 C 0.2782(4) -0.2500 0.2809(5) 0.0210(16) Uani 1 2 d S T P . .
C16 C 0.2713(4) -0.2500 0.2022(5) 0.0225(16) Uani 1 2 d S T P . .
H16 H 0.3078 -0.2500 0.1702 0.027 Uiso 1 2 calc R U P . .
C17 C 0.2108(4) -0.2500 0.1695(5) 0.0266(18) Uani 1 2 d S T P . .
C18 C 0.1589(4) -0.2500 0.2160(6) 0.0272(18) Uani 1 2 d S T P . .
H18 H 0.1179 -0.2500 0.1937 0.033 Uiso 1 2 calc R U P . .
C19 C 0.1644(4) -0.2500 0.2956(5) 0.0235(17) Uani 1 2 d S T P . .
C20 C 0.2247(4) -0.2500 0.3281(5) 0.0197(15) Uani 1 2 d S T P . .
H20 H 0.2294 -0.2500 0.3822 0.024 Uiso 1 2 calc R U P . .
C21 C 0.2047(5) -0.2500 0.0819(6) 0.035(2) Uani 1 2 d S T P . .
H21A H 0.2471 -0.2500 0.0589 0.052 Uiso 1 2 calc R U P . .
H21B H 0.1816 -0.3603 0.0655 0.052 Uiso 0.5 1 calc R U P . .
H21C H 0.1816 -0.1397 0.0655 0.052 Uiso 0.5 1 calc R U P . .
C22 C 0.1067(5) -0.2500 0.3464(7) 0.038(2) Uani 1 2 d S T P . .
H22A H 0.1199 -0.2500 0.4001 0.057 Uiso 1 2 calc R U P . .
H22B H 0.0813 -0.1397 0.3360 0.057 Uiso 0.5 1 calc R U P . .
H22C H 0.0813 -0.3603 0.3360 0.057 Uiso 0.5 1 calc R U P . .
N2 N 0.3370(3) -0.2500 0.3150(4) 0.0232(14) Uani 1 2 d S T P . .
Cl2 Cl 0.51002(11) -0.2500 0.42650(16) 0.0430(6) Uani 1 2 d S T P . .
W2 W 0.41019(2) -0.2500 0.36135(2) 0.01849(16) Uani 1 2 d S T P . .


_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 W1 2.099(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C4 C5 1.386(13) . ?
C4 N1 1.391(12) . ?
C4 C9 1.398(13) . ?
C5 C6 1.389(13) . ?
C5 H5 0.9500 . ?
C6 C7 1.389(14) . ?
C6 C10 1.527(14) . ?
C7 C8 1.398(14) . ?
C7 H7 0.9500 . ?
C8 C9 1.392(13) . ?
C8 C11 1.514(15) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C2 W1 2.103(10) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C12 W2 2.111(9) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N1 W1 1.731(8) . ?
Cl1 W1 2.404(3) . ?
W1 C1 2.099(6) 8_565 ?
C13 W2 2.081(6) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 N2 1.375(10) . ?
C15 C16 1.384(12) . ?
C15 C20 1.400(12) . ?
C16 C17 1.400(11) . ?
C16 H16 0.9500 . ?
C17 C18 1.364(14) . ?
C17 C21 1.536(12) . ?
C18 C19 1.395(13) . ?
C18 H18 0.9500 . ?
C19 C20 1.393(11) . ?
C19 C22 1.508(14) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
N2 W2 1.745(7) . ?
Cl2 W2 2.395(2) . ?
W2 C13 2.081(6) 8 ?

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
W1 C1 H1A 109.5 . . ?
W1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
W1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C5 C4 N1 120.5(9) . . ?
C5 C4 C9 120.1(9) . . ?
N1 C4 C9 119.4(8) . . ?
C4 C5 C6 121.5(9) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 117.9(9) . . ?
C7 C6 C10 121.0(9) . . ?
C5 C6 C10 121.1(9) . . ?
C6 C7 C8 121.8(9) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C9 C8 C7 119.4(9) . . ?
C9 C8 C11 120.8(9) . . ?
C7 C8 C11 119.8(10) . . ?
C8 C9 C4 119.3(9) . . ?
C8 C9 H9 120.4 . . ?
C4 C9 H9 120.4 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
W1 C2 H2A 109.5 . . ?
W1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
W1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
W2 C12 H12A 109.5 . . ?
W2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
W2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C4 N1 W1 176.3(7) . . ?
N1 W1 C1 91.9(2) . . ?
N1 W1 C1 91.9(2) . 8_565 ?
C1 W1 C1 118.0(4) . 8_565 ?
N1 W1 C2 95.1(4) . . ?
C1 W1 C2 120.6(2) . . ?
C1 W1 C2 120.6(2) 8_565 . ?
N1 W1 Cl1 176.9(3) . . ?
C1 W1 Cl1 86.5(2) . . ?
C1 W1 Cl1 86.5(2) 8_565 . ?
C2 W1 Cl1 88.0(3) . . ?
W2 C13 H13A 109.5 . . ?
W2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
W2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C15 C16 121.7(8) . . ?
N2 C15 C20 118.2(8) . . ?
C16 C15 C20 120.1(8) . . ?
C15 C16 C17 120.1(8) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 119.3(8) . . ?
C18 C17 C21 121.8(8) . . ?
C16 C17 C21 118.8(8) . . ?
C17 C18 C19 121.8(8) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C18 C19 C20 118.9(8) . . ?
C18 C19 C22 121.3(9) . . ?
C20 C19 C22 119.8(8) . . ?
C19 C20 C15 119.7(8) . . ?
C19 C20 H20 120.1 . . ?
C15 C20 H20 120.1 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C15 N2 W2 178.0(7) . . ?
N2 W2 C13 92.6(3) . 8 ?
N2 W2 C13 92.6(3) . . ?
C13 W2 C13 118.7(5) 8 . ?
N2 W2 C12 94.3(4) . . ?
C13 W2 C12 120.2(2) 8 . ?
C13 W2 C12 120.2(2) . . ?
N2 W2 Cl2 179.3(2) . . ?
C13 W2 Cl2 87.0(2) 8 . ?
C13 W2 Cl2 87.0(2) . . ?
C12 W2 Cl2 86.4(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
N1 C4 C5 C6 180.000(1) . . . . ?
C9 C4 C5 C6 0.000(1) . . . . ?
C4 C5 C6 C7 0.000(1) . . . . ?
C4 C5 C6 C10 180.000(0) . . . . ?
C5 C6 C7 C8 0.000(1) . . . . ?
C10 C6 C7 C8 180.000(1) . . . . ?
C6 C7 C8 C9 0.000(1) . . . . ?
C6 C7 C8 C11 180.000(1) . . . . ?
C7 C8 C9 C4 0.000(1) . . . . ?
C11 C8 C9 C4 180.000(1) . . . . ?
C5 C4 C9 C8 0.000(1) . . . . ?
N1 C4 C9 C8 180.000(1) . . . . ?
N2 C15 C16 C17 180.000(1) . . . . ?
C20 C15 C16 C17 0.000(1) . . . . ?
C15 C16 C17 C18 0.000(1) . . . . ?
C15 C16 C17 C21 180.000(1) . . . . ?
C16 C17 C18 C19 0.000(1) . . . . ?
C21 C17 C18 C19 180.000(1) . . . . ?
C17 C18 C19 C20 0.000(1) . . . . ?
C17 C18 C19 C22 180.000(1) . . . . ?
C18 C19 C20 C15 0.000(1) . . . . ?
C22 C19 C20 C15 180.000(1) . . . . ?
N2 C15 C20 C19 180.000(1) . . . . ?
C16 C15 C20 C19 0.000(1) . . . . ?

_refine_diff_density_max         2.518
_refine_diff_density_min         -1.752
_refine_diff_density_rms         0.254

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
_chemical_properties_physical    ', Air-sensitive,Moisture-sensitive'
####################################################################### 
# 
# 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_086ZRT15
_audit_block_doi                 10.5517/ccdc.csd.cc1mzdww
_database_code_depnum_ccdc_archive 'CCDC 1518779'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7QI00128B 2017
_audit_update_record             
;
2016-11-23 deposited with the CCDC.
2017-05-10 downloaded from the CCDC.
;
#WN-4-OMe-C6H4Me3Cl_2.7

# start Validation Reply Form
_vrf_PLAT342_086ZRT15            
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02333 Ang.  
RESPONSE: The data was refined as a two component twin with a 0.66:0.34
ratio. No restraints have been applied to any C-C bonds.
;
_vrf_PLAT987_086ZRT15            
;
PROBLEM: The Flack x is >> 0 -  Do a BASF/TWIN Refinement     Please Check
RESPONSE: The Flack test results are ambiguous. The data was refined as a two component twin with a 0.66:0.34 ratio. PLATON does not suggest a 
centrosymmetric spacegroup.
;
_vrf_STRVA01_086ZRT15            
;
PROBLEM: Flack test results are ambiguous.
RESPONSE: The Flack test results are ambiguous. The data was refined as a two component twin with a 0.66:0.34 ratio. PLATON does not suggest a 
centrosymmetric spacegroup.
;
_vrf_PLAT213_086ZRT15            
;
PROBLEM: Atom C10             has ADP max/min Ratio .....        3.8 prolat
RESPONSE: C10 is part of the para-methoxy group on the aryl ring. Visual 
inspection of the ellipsoid shows it to be elongated. This reflects the
thermal motion of this group well and modelling the disorder using PART 1
and PART 2 commands did not prove to be appropriate.
;
_vrf_PLAT220_086ZRT15            
;
PROBLEM: Large Non-Solvent  C     Ueq(max)/Ueq(min) Range        4.9 Ratio 
RESPONSE: C10 is part of the para-methoxy group on the aryl ring. Visual 
inspection of the ellipsoid shows it to be elongated. This reflects the
thermal motion of this group well and modelling the disorder using PART 1
and PART 2 commands did not prove to be appropriate.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H16 Cl N O W'
_chemical_formula_sum            'C10 H16 Cl N O W'
_chemical_formula_weight         385.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
W W -5.4734 5.5774 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   6.0476(3)
_cell_length_b                   7.3129(3)
_cell_length_c                   14.2223(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.885(4)
_cell_angle_gamma                90
_cell_volume                     623.04(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3439
_cell_measurement_theta_min      6.2740
_cell_measurement_theta_max      75.1430

_exptl_crystal_description       block
_exptl_crystal_colour            'pale orange'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.055
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    18.916
_shelx_estimated_absorpt_T_min   0.397
_shelx_estimated_absorpt_T_max   0.518
_exptl_absorpt_correction_T_min  0.73601
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            3247
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         6.283
_diffrn_reflns_theta_max         75.776
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
loop_
_diffrn_oxdiff_twin_id
_diffrn_oxdiff_twin_ratio
_diffrn_oxdiff_twin_reflns_isolated
_diffrn_oxdiff_twin_reflns_overlapped
1 0.6662 3004 2170
2 0.3338 3003 2170
_reflns_number_total             3247
_reflns_number_gt                3164
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.840
_reflns_Friedel_fraction_max     0.987
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    
;
'Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A. J. Appl. 
Cryst. 1994, 27, 435.'
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Burnett, M. N.; Johnson, C. K. 
ORTEP-III Report ORNL-6895. 
Oak Ridge National Laboratory, Tennessee, USA 1996.
;
_computing_publication_material  ?


_refine_special_details          
;
 Refined as a 2-component twin. Components in a 0.66/0.34 ratio.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0748P)²+2.5682P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.56(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3247
_refine_ls_number_parameters     119
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1084
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.359(5) 0.254(3) 0.645(2) 0.0253(16) Uani 1 1 d . U . . .
H1A H 0.4383 0.2272 0.7084 0.038 Uiso 1 1 calc R U . . .
H1B H 0.4662 0.2600 0.5994 0.038 Uiso 1 1 calc R U . . .
H1C H 0.2495 0.1576 0.6262 0.038 Uiso 1 1 calc R U . . .
C2 C -0.155(2) 0.521(3) 0.6239(9) 0.0253(16) Uani 1 1 d . U . . .
H2A H -0.2160 0.4050 0.5978 0.038 Uiso 1 1 calc R U . . .
H2B H -0.2009 0.6200 0.5787 0.038 Uiso 1 1 calc R U . . .
H2C H -0.2118 0.5463 0.6839 0.038 Uiso 1 1 calc R U . . .
C3 C 0.340(5) 0.769(3) 0.648(2) 0.0253(16) Uani 1 1 d . U . . .
H3A H 0.2238 0.8604 0.6286 0.038 Uiso 1 1 calc R U . . .
H3B H 0.4496 0.7714 0.6027 0.038 Uiso 1 1 calc R U . . .
H3C H 0.4152 0.7982 0.7115 0.038 Uiso 1 1 calc R U . . .
C4 C 0.220(2) 0.488(4) 0.8691(8) 0.018(3) Uani 1 1 d . . . . .
C5 C 0.051(3) 0.576(2) 0.9127(11) 0.030(3) Uani 1 1 d . . . . .
H5 H -0.0704 0.6348 0.8748 0.036 Uiso 1 1 calc R U . . .
C6 C 0.063(3) 0.577(3) 1.0121(11) 0.031(4) Uani 1 1 d . . . . .
H6 H -0.0585 0.6218 1.0411 0.038 Uiso 1 1 calc R U . . .
C7 C 0.248(2) 0.513(6) 1.0666(8) 0.030(4) Uani 1 1 d . . . . .
C8 C 0.415(3) 0.418(2) 1.0221(11) 0.029(3) Uani 1 1 d . . . . .
H8 H 0.5306 0.3519 1.0595 0.035 Uiso 1 1 calc R U . . .
C9 C 0.404(3) 0.423(3) 0.9245(12) 0.032(4) Uani 1 1 d . . . . .
H9 H 0.5272 0.3795 0.8957 0.039 Uiso 1 1 calc R U . . .
C10 C 0.103(4) 0.530(13) 1.2110(11) 0.088(16) Uani 1 1 d . U . . .
H10A H 0.1550 0.5233 1.2793 0.133 Uiso 1 1 calc R U . . .
H10B H 0.0330 0.6491 1.1958 0.133 Uiso 1 1 calc R U . . .
H10C H -0.0064 0.4327 1.1933 0.133 Uiso 1 1 calc R U . . .
N1 N 0.2072(19) 0.492(4) 0.7704(7) 0.021(3) Uani 1 1 d . . . . .
O1 O 0.2756(18) 0.509(6) 1.1630(6) 0.048(3) Uani 1 1 d . U . . .
W1 W 0.19428(8) 0.5062(4) 0.64786(3) 0.01817(19) Uani 1 1 d . U . . .
Cl1 Cl 0.1912(5) 0.5072(16) 0.47779(17) 0.0285(6) 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 W1 2.10(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 W1 2.097(13) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 W1 2.12(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C9 1.36(2) . ?
C4 N1 1.396(15) . ?
C4 C5 1.42(2) . ?
C5 C6 1.40(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.36(2) . ?
C6 H6 0.9500 . ?
C7 O1 1.359(14) . ?
C7 C8 1.44(3) . ?
C8 C9 1.38(2) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 O1 1.33(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
N1 W1 1.737(10) . ?
W1 Cl1 2.416(2) . ?

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
W1 C1 H1A 109.5 . . ?
W1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
W1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
W1 C2 H2A 109.5 . . ?
W1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
W1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
W1 C3 H3A 109.5 . . ?
W1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
W1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C9 C4 N1 121.0(15) . . ?
C9 C4 C5 119.3(13) . . ?
N1 C4 C5 119.1(16) . . ?
C6 C5 C4 119.9(15) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C7 C6 C5 120.0(15) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 O1 124.1(17) . . ?
C6 C7 C8 119.2(13) . . ?
O1 C7 C8 116(2) . . ?
C9 C8 C7 119.4(15) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C4 C9 C8 120.7(16) . . ?
C4 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 N1 W1 178(3) . . ?
C10 O1 C7 121.3(14) . . ?
N1 W1 C2 94.1(5) . . ?
N1 W1 C1 90.6(12) . . ?
C2 W1 C1 120.9(10) . . ?
N1 W1 C3 95.4(12) . . ?
C2 W1 C3 111.3(10) . . ?
C1 W1 C3 126.8(5) . . ?
N1 W1 Cl1 176.1(9) . . ?
C2 W1 Cl1 88.2(3) . . ?
C1 W1 Cl1 85.5(9) . . ?
C3 W1 Cl1 86.7(8) . . ?

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
C9 C4 C5 C6 -7(3) . . . . ?
N1 C4 C5 C6 -179(2) . . . . ?
C4 C5 C6 C7 8(3) . . . . ?
C5 C6 C7 O1 180(4) . . . . ?
C5 C6 C7 C8 -10(5) . . . . ?
C6 C7 C8 C9 12(4) . . . . ?
O1 C7 C8 C9 -177(3) . . . . ?
N1 C4 C9 C8 -179(2) . . . . ?
C5 C4 C9 C8 9(3) . . . . ?
C7 C8 C9 C4 -11(3) . . . . ?
C6 C7 O1 C10 15(9) . . . . ?
C8 C7 O1 C10 -155(5) . . . . ?

_refine_diff_density_max         1.386
_refine_diff_density_min         -1.653
_refine_diff_density_rms         0.181

_shelxl_version_number           2014-3


#===END

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
_chemical_properties_physical    ', Air-sensitive,Moisture-sensitive'
####################################################################### 
# 
# 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_014CW16-ZRT
_audit_block_doi                 10.5517/ccdc.csd.cc1mzdvv
_database_code_depnum_ccdc_archive 'CCDC 1518778'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7QI00128B 2017
_audit_update_record             
;
2016-11-23 deposited with the CCDC.
2017-05-10 downloaded from the CCDC.
;
#WN-2,6-F-C6H3-Me3Cl_2.5

# start Validation Reply Form
_vrf_PLAT910_014CW16-ZRT         
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min)          17 Note  
RESPONSE: Theta min limit set at 4 angstrom during data processing.
It is noted that _diffrn_reflns_theta_min is 5.180.
;
_vrf_PLAT972_014CW16-ZRT         
;
PROBLEM: Check Calcd Residual Density  0.79A From      W1      -2.92 eA-3  
RESPONSE: Majority of residual electron density is located about W1, N1,
C7, C8, C9 and Cl1; surrounding the central heavy W1. No indication of 
any additional unassigned atoms, or unaccounted for twinning.
;
# end Validation Reply Form


_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H12 Cl F2 N W'
_chemical_formula_sum            'C9 H12 Cl F2 N W'
_chemical_formula_weight         391.50

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.30920(10)
_cell_length_b                   7.50960(10)
_cell_length_c                   11.8873(2)
_cell_angle_alpha                90.1240(10)
_cell_angle_beta                 95.7700(10)
_cell_angle_gamma                118.5420(10)
_cell_volume                     569.340(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    11836
_cell_measurement_theta_min      5.097
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.284
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    10.367
_shelx_estimated_absorpt_T_min   0.305
_shelx_estimated_absorpt_T_max   0.424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7277
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
Multi-scan from symmetry-related measurements using
Sortav (Blessing 1995)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_type           Mok\a
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_number            4939
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         5.180
_diffrn_reflns_theta_max         27.544
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2615
_reflns_number_gt                2426
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    
;
Palatinus, L.; Chapuis, G. J. Appl. Cryst. 2007, 40, 786-790.
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0528P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2615
_refine_ls_number_parameters     130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0800
_refine_ls_wR_factor_gt          0.0780
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
W1 W 0.35494(2) 0.19824(2) 0.16472(2) 0.02128(10) Uani 1 1 d . . . . .
Cl1 Cl 0.3403(2) 0.1545(2) -0.03867(11) 0.0295(3) Uani 1 1 d . . . . .
F1 F 0.6266(5) 0.2106(5) 0.4792(3) 0.0364(7) Uani 1 1 d . . . . .
F2 F 0.0303(5) 0.2807(6) 0.3761(3) 0.0453(8) Uani 1 1 d . . . . .
N1 N 0.3495(6) 0.2264(6) 0.3106(4) 0.0249(9) Uani 1 1 d . . . . .
C1 C 0.3258(7) 0.2387(7) 0.4222(4) 0.0228(9) Uani 1 1 d . . . . .
C2 C 0.4621(8) 0.2283(7) 0.5107(4) 0.0272(10) Uani 1 1 d . . . . .
C3 C 0.4350(9) 0.2306(8) 0.6220(5) 0.0347(12) Uani 1 1 d . . . . .
H3 H 0.5296 0.2191 0.6786 0.042 Uiso 1 1 calc R U . . .
C4 C 0.2660(9) 0.2501(8) 0.6509(5) 0.0349(12) Uani 1 1 d . . . . .
H4 H 0.2435 0.2501 0.7282 0.042 Uiso 1 1 calc R U . . .
C5 C 0.1296(9) 0.2695(9) 0.5686(5) 0.0338(13) Uani 1 1 d . . . . .
H5 H 0.0163 0.2869 0.5886 0.041 Uiso 1 1 calc R U . . .
C6 C 0.1627(8) 0.2631(8) 0.4568(5) 0.0299(11) Uani 1 1 d . . . . .
C7 C 0.1816(8) -0.1209(7) 0.1604(4) 0.0274(10) Uani 1 1 d . . . . .
H7A H 0.1660 -0.1655 0.2379 0.041 Uiso 1 1 calc R U . . .
H7B H 0.2555 -0.1794 0.1226 0.041 Uiso 1 1 calc R U . . .
H7C H 0.0428 -0.1663 0.1186 0.041 Uiso 1 1 calc R U . . .
C8 C 0.6828(8) 0.3328(9) 0.1725(5) 0.0320(12) Uani 1 1 d . . . . .
H8A H 0.7358 0.4571 0.1309 0.048 Uiso 1 1 calc R U . . .
H8B H 0.7208 0.2378 0.1385 0.048 Uiso 1 1 calc R U . . .
H8C H 0.7447 0.3663 0.2518 0.048 Uiso 1 1 calc R U . . .
C9 C 0.2011(9) 0.3696(8) 0.1259(5) 0.0288(11) Uani 1 1 d . . . . .
H9A H 0.0589 0.2802 0.0894 0.043 Uiso 1 1 calc R U . . .
H9B H 0.2789 0.4743 0.0745 0.043 Uiso 1 1 calc R U . . .
H9C H 0.1937 0.4343 0.1958 0.043 Uiso 1 1 calc R 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
W1 N1 1.753(4) . ?
W1 C8 2.101(5) . ?
W1 C9 2.101(5) . ?
W1 C7 2.106(5) . ?
W1 Cl1 2.4239(13) . ?
F1 C2 1.358(6) . ?
F2 C6 1.345(6) . ?
N1 C1 1.365(6) . ?
C1 C6 1.389(7) . ?
C1 C2 1.403(7) . ?
C2 C3 1.358(8) . ?
C3 C4 1.387(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(8) . ?
C5 H5 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
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
N1 W1 C8 95.7(2) . . ?
N1 W1 C9 92.4(2) . . ?
C8 W1 C9 120.6(2) . . ?
N1 W1 C7 93.64(19) . . ?
C8 W1 C7 118.1(2) . . ?
C9 W1 C7 120.0(2) . . ?
N1 W1 Cl1 176.52(13) . . ?
C8 W1 Cl1 87.70(17) . . ?
C9 W1 Cl1 85.15(16) . . ?
C7 W1 Cl1 85.46(15) . . ?
C1 N1 W1 174.8(4) . . ?
N1 C1 C6 121.9(4) . . ?
N1 C1 C2 123.3(4) . . ?
C6 C1 C2 114.8(5) . . ?
C3 C2 F1 120.1(5) . . ?
C3 C2 C1 124.0(5) . . ?
F1 C2 C1 115.9(5) . . ?
C2 C3 C4 118.4(5) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C5 C4 C3 120.9(5) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C6 C5 C4 118.2(5) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
F2 C6 C5 118.7(5) . . ?
F2 C6 C1 117.7(5) . . ?
C5 C6 C1 123.6(5) . . ?
W1 C7 H7A 109.5 . . ?
W1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
W1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
W1 C8 H8A 109.5 . . ?
W1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
W1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
W1 C9 H9A 109.5 . . ?
W1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
W1 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
N1 C1 C2 C3 -176.7(5) . . . . ?
C6 C1 C2 C3 3.4(7) . . . . ?
N1 C1 C2 F1 1.8(7) . . . . ?
C6 C1 C2 F1 -178.1(4) . . . . ?
F1 C2 C3 C4 179.6(5) . . . . ?
C1 C2 C3 C4 -1.9(8) . . . . ?
C2 C3 C4 C5 -0.9(8) . . . . ?
C3 C4 C5 C6 1.9(8) . . . . ?
C4 C5 C6 F2 179.6(5) . . . . ?
C4 C5 C6 C1 -0.2(9) . . . . ?
N1 C1 C6 F2 -2.0(7) . . . . ?
C2 C1 C6 F2 177.9(4) . . . . ?
N1 C1 C6 C5 177.8(5) . . . . ?
C2 C1 C6 C5 -2.3(7) . . . . ?

_refine_diff_density_max         2.131
_refine_diff_density_min         -3.000
_refine_diff_density_rms         0.212

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
_chemical_properties_physical    ', Air-sensitive,Moisture-sensitive'
####################################################################### 
# 
# 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_005cw16
_audit_block_doi                 10.5517/ccdc.csd.cc1mzdll
_database_code_depnum_ccdc_archive 'CCDC 1518770'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7QI00128B 2017
_audit_update_record             
;
2016-11-23 deposited with the CCDC.
2017-05-10 downloaded from the CCDC.
;
#WN-2,6-Me-C6H3Cl4thf_1.3

# start Validation Reply Form
_vrf_PLAT910_005cw16             
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min)          24 Note  
RESPONSE: A data collection strategy was chosen to achieve 99% completeness
with twofold redundancy. The theta min limit was set to 4 angstrom during data
processing. It is noted that _cell_measurement_theta_min is 5.097.
;
_vrf_PLAT342_005cw16             
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............       0.01 Ang.  
RESPONSE: The structure was 99.3% complete to a theta value of 27.485.
The R(int) is 0.0512 and final R1 is 0.0564.
;
_vrf_PLAT241_005cw16             
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of         C9 Check 
RESPONSE: C9 is part of the tetrahydrofuran ring bound to W1. C9 is directly
bound to O1 and C8. Visual inspection of the thermal ellipsoid of C9 shows
it to be elongated slighlty in one direction, in keeping with the expected
movement of the bound solvent molecule. No further efforts to model this
movement were felt necessary.
;
_vrf_PLAT971_005cw16             
;
PROBLEM: Check Calcd Residual Density  1.05A From      N1       1.55 eA-3  
RESPONSE: This residual density is located near to N1 and does not suggest
any unassigned electron density. It is located at 1.46 angstrom to W1.
;
_vrf_PLAT972_005cw16             
;
PROBLEM: Check Calcd Residual Density  0.95A From      W1      -1.89 eA-3  
RESPONSE:  Deepest hole   -1.95  at  0.1983  0.5661  0.1845  [0.95 A from W1]
is located near the metal centre.
;
_vrf_PLAT977_005cw16             
;
PROBLEM: Check the Negative Difference Density on    H10A      -0.33 eA-3  
RESPONSE: C10 is a methylene carbon atom in the tetrahydrofuran ring.
The H atoms have been placed geometrically using a HFIX 23 command.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H17 Cl4 N O W'
_chemical_formula_sum            'C12 H17 Cl4 N O W'
_chemical_formula_weight         516.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9869(2)
_cell_length_b                   8.7291(2)
_cell_length_c                   12.9648(4)
_cell_angle_alpha                85.6090(10)
_cell_angle_beta                 89.9950(10)
_cell_angle_gamma                64.3290(10)
_cell_volume                     811.73(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    12755
_cell_measurement_theta_min      5.097
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.115
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    7.764
_shelx_estimated_absorpt_T_min   0.306
_shelx_estimated_absorpt_T_max   0.511
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_special_details   
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            6820
_diffrn_reflns_av_unetI/netI     0.0750
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         5.107
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3709
_reflns_number_gt                2978
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    
'L. Palatinus and G. Chapuis, J. Appl. Crystallogr., 2007, 40, 786-790.'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP, L. J. Farrugia, J. Appl. Crystallogr., 1997, 30, 565.'
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0387P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3709
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0865
_refine_ls_wR_factor_gt          0.0791
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0745(8) 0.9865(7) 0.3391(5) 0.0227(13) Uani 1 1 d . . . . .
C2 C -0.1017(9) 1.1270(8) 0.3167(5) 0.0292(14) Uani 1 1 d . . . . .
C3 C -0.1427(9) 1.2689(8) 0.3700(5) 0.0326(15) Uani 1 1 d . . . . .
H3 H -0.2593 1.3650 0.3568 0.039 Uiso 1 1 calc R U . . .
C4 C -0.0187(10) 1.2754(9) 0.4422(5) 0.0364(16) Uani 1 1 d . . . . .
H4 H -0.0506 1.3749 0.4778 0.044 Uiso 1 1 calc R U . . .
C5 C 0.1522(10) 1.1362(9) 0.4624(5) 0.0361(16) Uani 1 1 d . . . . .
H5 H 0.2357 1.1409 0.5129 0.043 Uiso 1 1 calc R U . . .
C6 C 0.2031(9) 0.9915(8) 0.4110(5) 0.0266(13) Uani 1 1 d . . . . .
C7 C -0.2373(9) 1.1202(9) 0.2400(6) 0.0419(18) Uani 1 1 d . . . . .
H7A H -0.3590 1.2164 0.2463 0.063 Uiso 1 1 calc R U . . .
H7B H -0.2481 1.0129 0.2534 0.063 Uiso 1 1 calc R U . . .
H7C H -0.1937 1.1268 0.1699 0.063 Uiso 1 1 calc R U . . .
C8 C 0.3893(9) 0.8414(9) 0.4307(5) 0.0361(16) Uani 1 1 d . . . . .
H8A H 0.4537 0.8594 0.4896 0.054 Uiso 1 1 calc R U . . .
H8B H 0.4636 0.8292 0.3691 0.054 Uiso 1 1 calc R U . . .
H8C H 0.3720 0.7377 0.4464 0.054 Uiso 1 1 calc R U . . .
C9 C 0.3048(13) 0.3912(9) 0.0419(5) 0.052(2) Uani 1 1 d . . . . .
H9A H 0.4051 0.4280 0.0314 0.062 Uiso 1 1 calc R U . . .
H9B H 0.2040 0.4552 -0.0108 0.062 Uiso 1 1 calc R U . . .
C10 C 0.3781(11) 0.2028(8) 0.0333(6) 0.0381(17) Uani 1 1 d . . . . .
H10A H 0.5156 0.1490 0.0324 0.046 Uiso 1 1 calc R U . . .
H10B H 0.3287 0.1804 -0.0309 0.046 Uiso 1 1 calc R U . . .
C11 C 0.3132(10) 0.1334(8) 0.1274(5) 0.0354(16) Uani 1 1 d . . . . .
H11A H 0.4186 0.0659 0.1769 0.043 Uiso 1 1 calc R U . . .
H11B H 0.2548 0.0600 0.1073 0.043 Uiso 1 1 calc R U . . .
C12 C 0.1728(10) 0.2895(8) 0.1748(5) 0.0359(16) Uani 1 1 d . . . . .
H12A H 0.0456 0.3220 0.1466 0.043 Uiso 1 1 calc R U . . .
H12B H 0.1745 0.2692 0.2510 0.043 Uiso 1 1 calc R U . . .
Cl1 Cl 0.0656(3) 0.7965(2) 0.06132(12) 0.0376(4) Uani 1 1 d . . . . .
Cl2 Cl 0.4709(2) 0.6140(2) 0.18126(13) 0.0344(4) Uani 1 1 d . . . . .
Cl3 Cl 0.3039(2) 0.45963(18) 0.36773(11) 0.0290(3) Uani 1 1 d . . . . .
Cl4 Cl -0.1134(2) 0.6506(2) 0.25302(14) 0.0335(4) Uani 1 1 d . . . . .
N1 N 0.1179(6) 0.8405(6) 0.2883(4) 0.0252(11) Uani 1 1 d . . . . .
O1 O 0.2349(6) 0.4216(5) 0.1447(3) 0.0307(10) Uani 1 1 d . . . . .
W1 W 0.17047(3) 0.65865(3) 0.22603(2) 0.02297(10) 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 N1 1.387(7) . ?
C1 C6 1.405(8) . ?
C1 C2 1.421(8) . ?
C2 C3 1.377(9) . ?
C2 C7 1.493(9) . ?
C3 C4 1.385(10) . ?
C4 C5 1.387(10) . ?
C5 C6 1.374(9) . ?
C6 C8 1.501(9) . ?
C9 O1 1.443(7) . ?
C9 C10 1.501(9) . ?
C10 C11 1.511(9) . ?
C11 C12 1.515(9) . ?
C12 O1 1.468(7) . ?
Cl1 W1 2.3331(16) . ?
Cl2 W1 2.3389(15) . ?
Cl3 W1 2.3316(14) . ?
Cl4 W1 2.3241(15) . ?
N1 W1 1.722(5) . ?
O1 W1 2.251(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
N1 C1 C6 119.8(5) . . ?
N1 C1 C2 118.3(5) . . ?
C6 C1 C2 122.0(5) . . ?
C3 C2 C1 117.0(6) . . ?
C3 C2 C7 121.5(6) . . ?
C1 C2 C7 121.5(6) . . ?
C2 C3 C4 121.9(6) . . ?
C3 C4 C5 119.8(6) . . ?
C6 C5 C4 121.3(6) . . ?
C5 C6 C1 118.0(6) . . ?
C5 C6 C8 121.8(6) . . ?
C1 C6 C8 120.2(5) . . ?
O1 C9 C10 106.6(5) . . ?
C9 C10 C11 106.0(5) . . ?
C10 C11 C12 105.0(5) . . ?
O1 C12 C11 103.6(5) . . ?
C1 N1 W1 179.5(5) . . ?
C9 O1 C12 106.5(5) . . ?
C9 O1 W1 126.1(4) . . ?
C12 O1 W1 125.9(4) . . ?
N1 W1 O1 179.18(19) . . ?
N1 W1 Cl4 95.51(16) . . ?
O1 W1 Cl4 83.67(12) . . ?
N1 W1 Cl3 97.96(17) . . ?
O1 W1 Cl3 82.20(12) . . ?
Cl4 W1 Cl3 90.36(6) . . ?
N1 W1 Cl1 96.33(17) . . ?
O1 W1 Cl1 83.54(12) . . ?
Cl4 W1 Cl1 90.47(6) . . ?
Cl3 W1 Cl1 165.53(6) . . ?
N1 W1 Cl2 96.69(16) . . ?
O1 W1 Cl2 84.12(12) . . ?
Cl4 W1 Cl2 167.80(6) . . ?
Cl3 W1 Cl2 87.85(5) . . ?
Cl1 W1 Cl2 88.30(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 178.6(5) . . . . ?
C6 C1 C2 C3 -0.8(9) . . . . ?
N1 C1 C2 C7 -0.7(9) . . . . ?
C6 C1 C2 C7 180.0(6) . . . . ?
C1 C2 C3 C4 -0.1(9) . . . . ?
C7 C2 C3 C4 179.1(6) . . . . ?
C2 C3 C4 C5 0.0(10) . . . . ?
C3 C4 C5 C6 1.0(10) . . . . ?
C4 C5 C6 C1 -1.8(9) . . . . ?
C4 C5 C6 C8 178.7(6) . . . . ?
N1 C1 C6 C5 -177.6(5) . . . . ?
C2 C1 C6 C5 1.7(9) . . . . ?
N1 C1 C6 C8 1.9(9) . . . . ?
C2 C1 C6 C8 -178.8(6) . . . . ?
O1 C9 C10 C11 10.8(9) . . . . ?
C9 C10 C11 C12 11.2(8) . . . . ?
C10 C11 C12 O1 -28.6(7) . . . . ?
C10 C9 O1 C12 -29.5(8) . . . . ?
C10 C9 O1 W1 163.7(5) . . . . ?
C11 C12 O1 C9 36.2(7) . . . . ?
C11 C12 O1 W1 -157.0(4) . . . . ?

_refine_diff_density_max         1.945
_refine_diff_density_min         -1.955
_refine_diff_density_rms         0.214

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
_chemical_properties_physical    ', Air-sensitive,Moisture-sensitive'
####################################################################### 
# 
# 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_tw001
_audit_block_doi                 10.5517/ccdc.csd.cc1mzdqq
_database_code_depnum_ccdc_archive 'CCDC 1518774'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7QI00128B 2017
_audit_update_record             
;
2016-11-23 deposited with the CCDC.
2017-05-10 downloaded from the CCDC.
;
#WN-4-OMe-C6H4Cl4thf_1.7

# start Validation Reply Form
_vrf_PLAT019_tw001               
;
PROBLEM: _diffrn_measured_fraction_theta_full/_max < 1.0      0.998 Report
RESPONSE: A data collection strategy was chosen to obtain 99.5% completeness
and 4-fold redundancy based on a monoclinic crystal system. Data were cut off
for processing at a resolution limit of 0.75 angstrom. 
;
_vrf_PLAT241_tw001               
;
PROBLEM: High      Ueq as Compared to Neighbors for .....         C8 Check 
RESPONSE: C8 is part of the metal-coordinated thf molecule. Visual inspection
of the themal ellipsoids show that the slightly elongated ellipsoid of C8
is consistent with the motion of the solvent molecule. C8 is also bound to O1 
which displays relatively little movement.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H15 Cl4 N O2 W'
_chemical_formula_sum            'C11 H15 Cl4 N O2 W'
_chemical_formula_weight         518.89

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'
Cl Cl 0.1484 0.1585 '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'
W W -0.8490 6.8722 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   13.2115(2)
_cell_length_b                   8.08220(10)
_cell_length_c                   15.7475(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.1090(10)
_cell_angle_gamma                90
_cell_volume                     1588.83(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    19332
_cell_measurement_theta_min      5.097
_cell_measurement_theta_max      28.283

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.169
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    7.939
_shelx_estimated_absorpt_T_min   0.300
_shelx_estimated_absorpt_T_max   0.504
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.735
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
Multi-scan from symmetry-related measurements using
Sortav (Blessing 1995)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7374
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         5.181
_diffrn_reflns_theta_max         28.274
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3921
_reflns_number_gt                3396
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    
;
SHELXS-2013 - Sheldrick, G. M. Acta Crystallogr., Sect. A 2008, 64, 112-122.
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0441P)²+0.2202P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3921
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0754
_refine_ls_wR_factor_gt          0.0719
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1838(3) 0.4301(4) 0.3791(3) 0.0217(7) Uani 1 1 d . . . . .
C2 C 0.0897(3) 0.3397(4) 0.3446(2) 0.0265(7) Uani 1 1 d . . . . .
H2 H 0.0647 0.2728 0.3832 0.032 Uiso 1 1 calc R U . . .
C3 C 0.0326(3) 0.3477(4) 0.2534(2) 0.0267(7) Uani 1 1 d . . . . .
H3 H -0.0314 0.2853 0.2291 0.032 Uiso 1 1 calc R U . . .
C4 C 0.0693(3) 0.4476(4) 0.1976(3) 0.0234(7) Uani 1 1 d . . . . .
C5 C 0.1638(3) 0.5381(4) 0.2334(3) 0.0238(7) Uani 1 1 d . . . . .
H5 H 0.1884 0.6064 0.1950 0.029 Uiso 1 1 calc R U . . .
C6 C 0.2217(3) 0.5295(5) 0.3233(2) 0.0249(7) Uani 1 1 d . . . . .
H6 H 0.2865 0.5901 0.3473 0.030 Uiso 1 1 calc R U . . .
C7 C -0.0786(3) 0.3766(6) 0.0674(3) 0.0353(8) Uani 1 1 d . . . . .
H7A H -0.0638 0.2577 0.0748 0.053 Uiso 1 1 calc R U . . .
H7B H -0.1063 0.4035 0.0032 0.053 Uiso 1 1 calc R U . . .
H7C H -0.1319 0.4066 0.0958 0.053 Uiso 1 1 calc R U . . .
C8 C 0.3148(5) 0.5551(6) 0.7907(3) 0.0518(13) Uani 1 1 d . . . . .
H8A H 0.2360 0.5699 0.7679 0.062 Uiso 1 1 calc R U . . .
H8B H 0.3491 0.6634 0.7891 0.062 Uiso 1 1 calc R U . . .
C9 C 0.3493(4) 0.4886(7) 0.8831(3) 0.0442(10) Uani 1 1 d . . . . .
H9A H 0.2906 0.4257 0.8942 0.053 Uiso 1 1 calc R U . . .
H9B H 0.3715 0.5793 0.9277 0.053 Uiso 1 1 calc R U . . .
C10 C 0.4412(4) 0.3786(6) 0.8891(3) 0.0433(10) Uani 1 1 d . . . . .
H10A H 0.4431 0.2840 0.9296 0.052 Uiso 1 1 calc R U . . .
H10B H 0.5096 0.4399 0.9123 0.052 Uiso 1 1 calc R U . . .
C11 C 0.4237(4) 0.3200(6) 0.7960(3) 0.0482(11) Uani 1 1 d . . . . .
H11A H 0.4920 0.3198 0.7828 0.058 Uiso 1 1 calc R U . . .
H11B H 0.3943 0.2062 0.7880 0.058 Uiso 1 1 calc R U . . .
Cl1 Cl 0.29620(8) 0.14147(12) 0.60376(7) 0.0334(2) Uani 1 1 d . . . . .
Cl2 Cl 0.12390(8) 0.44022(12) 0.60406(8) 0.0349(2) Uani 1 1 d . . . . .
Cl3 Cl 0.30429(7) 0.71528(11) 0.59766(6) 0.02552(19) Uani 1 1 d . . . . .
Cl4 Cl 0.47368(8) 0.42027(10) 0.60209(7) 0.0290(2) Uani 1 1 d . . . . .
O1 O 0.0186(2) 0.4675(3) 0.10904(17) 0.0295(6) Uani 1 1 d . . . . .
O2 O 0.3479(2) 0.4341(3) 0.73646(19) 0.0258(6) Uani 1 1 d . . . . .
W1 W 0.29132(2) 0.42649(2) 0.58613(2) 0.01943(7) Uani 1 1 d . . . . .
N1 N 0.2390(3) 0.4258(3) 0.4698(2) 0.0223(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.375(6) . ?
C1 C2 1.390(5) . ?
C1 C6 1.398(5) . ?
C2 C3 1.388(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(5) . ?
C3 H3 0.9500 . ?
C4 O1 1.344(5) . ?
C4 C5 1.397(5) . ?
C5 C6 1.374(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.438(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 O2 1.457(5) . ?
C8 C9 1.477(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.482(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.486(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 O2 1.455(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
Cl1 W1 2.3186(10) . ?
Cl2 W1 2.3224(10) . ?
Cl3 W1 2.3431(9) . ?
Cl4 W1 2.3395(9) . ?
O2 W1 2.238(3) . ?
W1 N1 1.733(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
N1 C1 C2 119.7(3) . . ?
N1 C1 C6 119.3(4) . . ?
C2 C1 C6 121.0(4) . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
O1 C4 C3 124.5(3) . . ?
O1 C4 C5 115.6(3) . . ?
C3 C4 C5 120.0(3) . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 119.0(3) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 C9 106.1(4) . . ?
O2 C8 H8A 110.5 . . ?
C9 C8 H8A 110.5 . . ?
O2 C8 H8B 110.5 . . ?
C9 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
C8 C9 C10 105.3(4) . . ?
C8 C9 H9A 110.7 . . ?
C10 C9 H9A 110.7 . . ?
C8 C9 H9B 110.7 . . ?
C10 C9 H9B 110.7 . . ?
H9A C9 H9B 108.8 . . ?
C9 C10 C11 105.6(3) . . ?
C9 C10 H10A 110.6 . . ?
C11 C10 H10A 110.6 . . ?
C9 C10 H10B 110.6 . . ?
C11 C10 H10B 110.6 . . ?
H10A C10 H10B 108.8 . . ?
O2 C11 C10 106.6(3) . . ?
O2 C11 H11A 110.4 . . ?
C10 C11 H11A 110.4 . . ?
O2 C11 H11B 110.4 . . ?
C10 C11 H11B 110.4 . . ?
H11A C11 H11B 108.6 . . ?
C4 O1 C7 118.6(3) . . ?
C11 O2 C8 108.9(3) . . ?
C11 O2 W1 125.8(2) . . ?
C8 O2 W1 125.3(2) . . ?
N1 W1 O2 176.02(12) . . ?
N1 W1 Cl1 96.27(9) . . ?
O2 W1 Cl1 85.07(6) . . ?
N1 W1 Cl2 93.59(11) . . ?
O2 W1 Cl2 82.62(8) . . ?
Cl1 W1 Cl2 91.33(3) . . ?
N1 W1 Cl4 98.84(11) . . ?
O2 W1 Cl4 84.92(8) . . ?
Cl1 W1 Cl4 88.77(3) . . ?
Cl2 W1 Cl4 167.49(4) . . ?
N1 W1 Cl3 94.52(9) . . ?
O2 W1 Cl3 84.27(6) . . ?
Cl1 W1 Cl3 169.10(4) . . ?
Cl2 W1 Cl3 89.50(3) . . ?
Cl4 W1 Cl3 88.08(3) . . ?
C1 N1 W1 171.9(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
N1 C1 C2 C3 178.2(3) . . . . ?
C6 C1 C2 C3 0.1(5) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
C2 C3 C4 O1 -178.2(3) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
O1 C4 C5 C6 179.1(3) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
C4 C5 C6 C1 -0.8(5) . . . . ?
N1 C1 C6 C5 -177.5(3) . . . . ?
C2 C1 C6 C5 0.6(5) . . . . ?
O2 C8 C9 C10 25.6(6) . . . . ?
C8 C9 C10 C11 -27.2(6) . . . . ?
C9 C10 C11 O2 18.7(6) . . . . ?
C3 C4 O1 C7 -1.9(5) . . . . ?
C5 C4 O1 C7 179.3(3) . . . . ?
C10 C11 O2 C8 -2.8(5) . . . . ?
C10 C11 O2 W1 177.0(3) . . . . ?
C9 C8 O2 C11 -14.2(5) . . . . ?
C9 C8 O2 W1 166.0(3) . . . . ?

_refine_diff_density_max         1.744
_refine_diff_density_min         -1.671
_refine_diff_density_rms         0.193

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: pentane'
_chemical_properties_physical    ', Air-sensitive,Moisture-sensitive'
####################################################################### 
# 
# 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_015CW16-ZRT
_audit_block_doi                 10.5517/ccdc.csd.cc1mzdrr
_database_code_depnum_ccdc_archive 'CCDC 1518775'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7QI00128B 2017
_audit_update_record             
;
2016-11-23 deposited with the CCDC.
2017-05-10 downloaded from the CCDC.
;
#WN-3,5-Me-C6H3-Cl4thf_1.8

# start Validation Reply Form
_vrf_PLAT910_015CW16-ZRT         
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min)          29 Note  
RESPONSE: A data collection strategy was chosen to achieve 99% completeness
with twofold redundancy. The theta min limit was set to 4 angstrom during data
processing. It is noted that _cell_measurement_theta_min is 5.10.
;

_vrf_PLAT213_015CW16-ZRT         
;
PROBLEM: Atom C9              has ADP max/min Ratio .....        3.2 prolat
RESPONSE: C9 is part of the tetrahydrofuran molecule coordinate to W1. C9 is bound  
to O1 and C10. Visual inspection of the thermal ellipsoid of C0 demonstrates it
to be elongated (especically with respect to O1 and C10), indicative of high thermal motion but consistent with the expected movement of the tetrahydrofuran fragement. 
It was not deemed suitable to model the disorder using PART commands, though DELU restraints have been applied.
;
_vrf_PLAT241_015CW16-ZRT         
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of         C9 Check 
RESPONSE: C9 is part of the tetrahydrofuran molecule coordinate to W1. C9 is bound  
to O1 and C10. Visual inspection of the thermal ellipsoid of C0 demonstrates it
to be elongated (especically with respect to O1 and C10), indicative of high thermal motion but consistent with the expected movement of the tetrahydrofuran fragement. 
It was not deemed suitable to model the disorder using PART commands, though DELU restraints have been applied.
;
_vrf_PLAT242_015CW16-ZRT         
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         O1 Check 
RESPONSE: C9 is part of the tetrahydrofuran molecule coordinate to W1. C9 is bound  
to O1 and C10. Visual inspection of the thermal ellipsoid of C0 demonstrates it
to be elongated (especically with respect to O1 and C10), indicative of high thermal motion but consistent with the expected movement of the tetrahydrofuran fragement. 
It was not deemed suitable to model the disorder using PART commands, though DELU restraints have been applied.
;
_vrf_PLAT975_015CW16-ZRT         
;
PROBLEM: Check Calcd Residual Density  1.09A From      O1       0.66 eA-3  
RESPONSE: The residual electron density 1.09 angstrom from O1 is low and
is not in a position indicative of any unassigned atoms.
;
_vrf_PLAT977_015CW16-ZRT         
;
PROBLEM: Check the Negative Difference Density on     H7A      -0.38 eA-3  
RESPONSE: Hydrogen atoms were placed on H7A using and AFIX 137 command,
calculating the torsion angle from the electron density. There is no indication
that the group needs to be modelled as a disordered methyl group with two positions.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H17 Cl4 N O W'
_chemical_formula_sum            'C12 H17 Cl4 N O W'
_chemical_formula_weight         516.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.63540(10)
_cell_length_b                   9.6261(2)
_cell_length_c                   10.9204(2)
_cell_angle_alpha                101.4700(10)
_cell_angle_beta                 95.2400(10)
_cell_angle_gamma                107.5340(10)
_cell_volume                     837.11(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3766
_cell_measurement_theta_min      5.10
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.051
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    7.529
_shelx_estimated_absorpt_T_min   0.314
_shelx_estimated_absorpt_T_max   0.520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            7196
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_av_R_equivalents  0.0252
_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       14
_diffrn_reflns_theta_min         5.106
_diffrn_reflns_theta_max         27.521
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3819
_reflns_number_gt                3471
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    
;
SUPERFLIP
Palatinus, L.; Chapuis, G. J. Appl. Cryst. 2007, 40, 786-790.
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0282P)²+0.7360P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3819
_refine_ls_number_parameters     175
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0647
_refine_ls_wR_factor_gt          0.0626
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_restrained_S_all      1.125
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4383(5) 0.8384(5) 0.1418(4) 0.0227(8) Uani 1 1 d . . . . .
C2 C 0.5523(5) 0.9813(5) 0.1889(4) 0.0251(8) Uani 1 1 d . . . . .
H2 H 0.5367 1.0475 0.2601 0.030 Uiso 1 1 calc R U . . .
C3 C 0.6899(5) 1.0263(5) 0.1303(4) 0.0251(9) Uani 1 1 d . . . . .
C4 C 0.7068(5) 0.9262(5) 0.0263(4) 0.0284(9) Uani 1 1 d . . . . .
H4 H 0.8004 0.9562 -0.0138 0.034 Uiso 1 1 calc R U . . .
C5 C 0.5919(5) 0.7825(5) -0.0223(4) 0.0284(9) Uani 1 1 d . . . . .
C6 C 0.4562(5) 0.7381(5) 0.0371(4) 0.0246(8) Uani 1 1 d . . . . .
H6 H 0.3767 0.6411 0.0070 0.029 Uiso 1 1 calc R U . . .
C7 C 0.8141(6) 1.1798(5) 0.1790(4) 0.0351(10) Uani 1 1 d . . . . .
H7A H 0.8759 1.2078 0.1117 0.053 Uiso 1 1 calc R U . . .
H7B H 0.8901 1.1796 0.2513 0.053 Uiso 1 1 calc R U . . .
H7C H 0.7577 1.2523 0.2058 0.053 Uiso 1 1 calc R U . . .
C8 C 0.6126(7) 0.6807(6) -0.1386(4) 0.0406(11) Uani 1 1 d . . . . .
H8A H 0.5704 0.5763 -0.1321 0.061 Uiso 1 1 calc R U . . .
H8B H 0.7296 0.7065 -0.1460 0.061 Uiso 1 1 calc R U . . .
H8C H 0.5515 0.6930 -0.2136 0.061 Uiso 1 1 calc R U . . .
Cl1 Cl -0.06090(14) 0.65962(14) 0.08115(10) 0.0355(3) Uani 1 1 d . . . . .
Cl2 Cl 0.11372(14) 0.51939(12) 0.28275(11) 0.0314(2) Uani 1 1 d . . . . .
Cl3 Cl 0.26156(13) 0.84970(13) 0.47728(10) 0.0357(3) Uani 1 1 d . . . . .
Cl4 Cl 0.09503(15) 0.99415(12) 0.27568(12) 0.0394(3) Uani 1 1 d . . . . .
N1 N 0.2995(4) 0.7981(4) 0.1983(3) 0.0257(7) Uani 1 1 d . . . . .
W1 W 0.12546(2) 0.75983(2) 0.26816(2) 0.02137(7) Uani 1 1 d . . . . .
O1 O -0.1026(3) 0.7154(3) 0.3571(3) 0.0248(6) Uani 1 1 d . U . . .
C10 C -0.3669(6) 0.7062(6) 0.4059(5) 0.0388(11) Uani 1 1 d . U . . .
H10A H -0.4775 0.6482 0.3565 0.047 Uiso 1 1 calc R U . . .
H10B H -0.3748 0.7942 0.4665 0.047 Uiso 1 1 calc R U . . .
C12 C -0.1232(6) 0.6569(7) 0.4701(5) 0.0418(12) Uani 1 1 d . U . . .
H12A H -0.0613 0.7352 0.5468 0.050 Uiso 1 1 calc R U . . .
H12B H -0.0831 0.5701 0.4646 0.050 Uiso 1 1 calc R U . . .
C11 C -0.3024(6) 0.6105(7) 0.4746(6) 0.0498(14) Uani 1 1 d . U . . .
H11A H -0.3226 0.6274 0.5633 0.060 Uiso 1 1 calc R U . . .
H11B H -0.3561 0.5030 0.4325 0.060 Uiso 1 1 calc R U . . .
C9 C -0.2476(7) 0.7552(9) 0.3201(7) 0.067(2) Uani 1 1 d . U . . .
H9A H -0.2965 0.7039 0.2308 0.081 Uiso 1 1 calc R U . . .
H9B H -0.2172 0.8649 0.3290 0.081 Uiso 1 1 calc R 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 1.385(5) . ?
C1 C2 1.392(6) . ?
C1 C6 1.395(6) . ?
C2 C3 1.395(6) . ?
C3 C4 1.385(6) . ?
C3 C7 1.498(6) . ?
C4 C5 1.402(6) . ?
C5 C6 1.387(6) . ?
C5 C8 1.503(6) . ?
Cl1 W1 2.3178(11) . ?
Cl2 W1 2.3239(10) . ?
Cl3 W1 2.3358(10) . ?
Cl4 W1 2.3347(11) . ?
N1 W1 1.722(3) . ?
W1 O1 2.239(3) . ?
O1 C12 1.458(5) . ?
O1 C9 1.462(5) . ?
C10 C9 1.491(7) . ?
C10 C11 1.493(7) . ?
C12 C11 1.485(6) . ?

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 C2 118.3(4) . . ?
N1 C1 C6 119.5(4) . . ?
C2 C1 C6 122.2(4) . . ?
C1 C2 C3 119.2(4) . . ?
C4 C3 C2 118.3(4) . . ?
C4 C3 C7 121.5(4) . . ?
C2 C3 C7 120.2(4) . . ?
C3 C4 C5 122.9(4) . . ?
C6 C5 C4 118.5(4) . . ?
C6 C5 C8 120.8(4) . . ?
C4 C5 C8 120.6(4) . . ?
C5 C6 C1 118.9(4) . . ?
C1 N1 W1 176.0(3) . . ?
N1 W1 O1 178.37(12) . . ?
N1 W1 Cl1 96.16(12) . . ?
O1 W1 Cl1 83.29(8) . . ?
N1 W1 Cl2 96.58(12) . . ?
O1 W1 Cl2 84.96(8) . . ?
Cl1 W1 Cl2 89.85(4) . . ?
N1 W1 Cl4 94.46(12) . . ?
O1 W1 Cl4 84.01(8) . . ?
Cl1 W1 Cl4 90.09(5) . . ?
Cl2 W1 Cl4 168.90(4) . . ?
N1 W1 Cl3 96.39(12) . . ?
O1 W1 Cl3 84.16(8) . . ?
Cl1 W1 Cl3 167.45(4) . . ?
Cl2 W1 Cl3 88.78(4) . . ?
Cl4 W1 Cl3 88.87(5) . . ?
C12 O1 C9 108.9(3) . . ?
C12 O1 W1 125.2(2) . . ?
C9 O1 W1 125.6(3) . . ?
C9 C10 C11 106.2(4) . . ?
O1 C12 C11 105.8(4) . . ?
C12 C11 C10 105.4(4) . . ?
O1 C9 C10 106.8(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
N1 C1 C2 C3 -177.5(3) . . . . ?
C6 C1 C2 C3 -0.3(6) . . . . ?
C1 C2 C3 C4 0.3(6) . . . . ?
C1 C2 C3 C7 179.8(4) . . . . ?
C2 C3 C4 C5 0.2(6) . . . . ?
C7 C3 C4 C5 -179.4(4) . . . . ?
C3 C4 C5 C6 -0.7(6) . . . . ?
C3 C4 C5 C8 177.4(4) . . . . ?
C4 C5 C6 C1 0.7(6) . . . . ?
C8 C5 C6 C1 -177.4(4) . . . . ?
N1 C1 C6 C5 177.0(3) . . . . ?
C2 C1 C6 C5 -0.2(6) . . . . ?
C9 O1 C12 C11 19.9(6) . . . . ?
W1 O1 C12 C11 -166.2(3) . . . . ?
O1 C12 C11 C10 -26.5(6) . . . . ?
C9 C10 C11 C12 23.2(7) . . . . ?
C12 O1 C9 C10 -5.4(7) . . . . ?
W1 O1 C9 C10 -179.2(3) . . . . ?
C11 C10 C9 O1 -11.2(7) . . . . ?

_refine_diff_density_max         1.615
_refine_diff_density_min         -1.414
_refine_diff_density_rms         0.156

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
_chemical_properties_physical    ', Air-sensitive,Moisture-sensitive'
####################################################################### 
# 
# 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_012cw16-ZRT
_audit_block_doi                 10.5517/ccdc.csd.cc1mzdtt
_database_code_depnum_ccdc_archive 'CCDC 1518777'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7QI00128B 2017
_audit_update_record             
;
2016-11-23 deposited with the CCDC.
2017-05-10 downloaded from the CCDC.
;
#WNPhMe3Cl_2.4

# start Validation Reply Form
_vrf_PLAT910_012cw16-ZRT         
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min)          12 Note  
RESPONSE: A data collection strategy was chosen to target 99% completeness
and a redundancy of 2.00. On data processing, beam stop limit was set to 4
angstroms. The cell_measurement theta min is recorded as 5.097 angstroms.
;

# start Validation Reply Form
_vrf_PLAT971_012cw16-ZRT         
;
PROBLEM: Check Calcd Residual Density  1.14A From      C2       1.54 eA-3  
RESPONSE: Q1 is located at  1.0141,0.2500,0.0006 (x,y,z) with nearest
non-H atom C2 located at 1.16 angstrom. The molecule lies on a special
position and was also disordered; this has been modelled using two components.
;
_vrf_PLAT972_012cw16-ZRT         
;
PROBLEM: Check Calcd Residual Density  0.83A From      W1      -1.99 eA-3  
RESPONSE:  Deepest hole   -2.13  at  0.6136  0.1790  0.3804  [  0.84 A from W1 ]:
this lies within 1 angstrom of the heaviest atom W1.
;
_vrf_PLAT977_012cw16-ZRT         
;
PROBLEM: Check the Negative Difference Density on      H4      -0.31 eA-3  
RESPONSE: H4 is bound to aromatic carbon atom C4 and has been placed using
HFIX 43. H7C, H8A/H8B/H8C are all bound to methyl carbon atoms C7
and C8 respectively. They have been placed using HFIX 137. Note also that
The molecule lies on a special position and was also disordered; 
this has been modelled using two components.
;

# end Validation Reply Form

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H14 Cl N W'
_chemical_formula_sum            'C9 H14 Cl N W'
_chemical_formula_weight         355.51

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'
Cl Cl 0.1484 0.1585 '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'
W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

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

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

_cell_length_a                   6.3636(2)
_cell_length_b                   7.2907(2)
_cell_length_c                   11.9698(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.495(2)
_cell_angle_gamma                90
_cell_volume                     554.31(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4698
_cell_measurement_theta_min      5.097
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.130
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    10.611
_shelx_estimated_absorpt_T_min   0.225
_shelx_estimated_absorpt_T_max   0.417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6953
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
Multi-scan from symmetry-related measurements using
Sortav (Blessing 1995)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2527
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         5.119
_diffrn_reflns_theta_max         27.529
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             1367
_reflns_number_gt                1208
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    
;
SIR-92
Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A. J. 
Appl. Cryst. 1994, 27, 435.
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0522P)²+1.9381P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1367
_refine_ls_number_parameters     77
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0944
_refine_ls_wR_factor_gt          0.0913
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
W1 W 0.66430(6) 0.2500 0.33384(3) 0.02155(16) Uani 1 2 d S T P A .
Cl1 Cl 0.6594(4) 0.2500 0.53540(19) 0.0291(5) Uani 1 2 d S T P . .
N1 N 0.6840(14) 0.2500 0.1895(7) 0.0244(18) Uani 1 2 d S T P . .
C1 C 0.7105(14) 0.236(2) 0.0758(5) 0.026(3) Uani 0.5 1 d G . P A -1
C2 C 0.8907(12) 0.1553(18) 0.0379(6) 0.029(3) Uani 0.5 1 d G . P A -1
H2 H 0.9955 0.1077 0.0900 0.035 Uiso 0.5 1 calc R U P A -1
C3 C 0.9177(14) 0.1441(17) -0.0763(7) 0.042(4) Uani 0.5 1 d G . P A -1
H3 H 1.0409 0.0889 -0.1022 0.050 Uiso 0.5 1 calc R U P A -1
C4 C 0.7645(18) 0.2137(19) -0.1525(5) 0.043(7) Uani 0.5 1 d G . P A -1
H4 H 0.7830 0.2061 -0.2305 0.052 Uiso 0.5 1 calc R U P A -1
C5 C 0.5843(16) 0.2945(15) -0.1145(7) 0.045(5) Uani 0.5 1 d G . P A -1
H5 H 0.4796 0.3421 -0.1666 0.054 Uiso 0.5 1 calc R U P A -1
C6 C 0.5573(13) 0.3057(17) -0.0004(7) 0.035(4) Uani 0.5 1 d G . P A -1
H6 H 0.4341 0.3609 0.0256 0.042 Uiso 0.5 1 calc R U P A -1
C7 C 0.8211(11) -0.0050(11) 0.3529(6) 0.0278(14) Uani 1 1 d . . . . .
H7A H 0.8220 -0.0663 0.2801 0.042 Uiso 1 1 calc R U . A .
H7B H 0.7476 -0.0822 0.4051 0.042 Uiso 1 1 calc R U . . .
H7C H 0.9662 0.0154 0.3824 0.042 Uiso 1 1 calc R U . . .
C8 C 0.3342(17) 0.2500 0.3269(10) 0.036(3) Uani 1 2 d S T P . .
H8A H 0.2860 0.2500 0.4031 0.054 Uiso 1 2 calc R U P A .
H8B H 0.2812 0.3598 0.2872 0.054 Uiso 0.5 1 calc R U P . .
H8C H 0.2812 0.1402 0.2872 0.054 Uiso 0.5 1 calc R U P . .


_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 N1 1.740(8) . ?
W1 C8 2.097(11) . ?
W1 C7 2.115(8) 4_565 ?
W1 C7 2.115(8) . ?
W1 Cl1 2.415(2) . ?
N1 C1 1.384(10) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 C3 1.3900 . ?
C2 H2 0.9500 . ?
C3 C4 1.3900 . ?
C3 H3 0.9500 . ?
C4 C5 1.3900 . ?
C4 H4 0.9500 . ?
C5 C6 1.3900 . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 W1 C8 95.4(4) . . ?
N1 W1 C7 92.6(2) . 4_565 ?
C8 W1 C7 118.0(2) . 4_565 ?
N1 W1 C7 92.6(2) . . ?
C8 W1 C7 118.0(2) . . ?
C7 W1 C7 123.0(4) 4_565 . ?
N1 W1 Cl1 176.6(3) . . ?
C8 W1 Cl1 88.0(3) . . ?
C7 W1 Cl1 85.81(19) 4_565 . ?
C7 W1 Cl1 85.81(19) . . ?
C1 N1 W1 174.9(6) . . ?
N1 C1 C2 120.3(7) . . ?
N1 C1 C6 119.7(7) . . ?
C2 C1 C6 120.0 . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
W1 C7 H7A 109.5 . . ?
W1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
W1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
W1 C8 H8A 109.5 . . ?
W1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
W1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -179.1(12) . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
N1 C1 C6 C5 179.1(12) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?

_refine_diff_density_max         1.895
_refine_diff_density_min         -2.126
_refine_diff_density_rms         0.251

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
_chemical_properties_physical    ', Air-sensitive,Moisture-sensitive'
####################################################################### 
# 
# 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_027ZRT16
_audit_block_doi                 10.5517/ccdc.csd.cc1mzdpp
_database_code_depnum_ccdc_archive 'CCDC 1518773'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7QI00128B 2017
_audit_update_record             
;
2016-11-23 deposited with the CCDC.
2017-05-10 downloaded from the CCDC.
;
#WN-3,5-CF3-C6H3Cl4thf_1.6

# start Validation Reply Form
_vrf_PLAT910_027ZRT16            
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min)          32 Note  
RESPONSE: On data processing, the beam stop limit was set to 4
angstroms. The cell_measurement theta min is recorded as 5.097 angstroms.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H11 Cl4 F6 N O W'
_chemical_formula_sum            'C12 H11 Cl4 F6 N O W'
_chemical_formula_weight         624.87

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'
F F 0.0171 0.0103 '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'
W W -0.8490 6.8722 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.99180(10)
_cell_length_b                   10.37140(10)
_cell_length_c                   10.97200(10)
_cell_angle_alpha                63.4270(10)
_cell_angle_beta                 86.0470(10)
_cell_angle_gamma                89.3590(10)
_cell_volume                     912.736(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    18213
_cell_measurement_theta_min      5.097
_cell_measurement_theta_max      27.485

_exptl_crystal_description       shard
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.274
_exptl_crystal_F_000             588
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    6.972
_shelx_estimated_absorpt_T_min   0.336
_shelx_estimated_absorpt_T_max   0.542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.714
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
Multi-scan from symmetry-related measurements using
Sortav (Blessing 1995)
;

_exptl_special_details           
;
 ?
;


_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7916
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.135
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4161
_reflns_number_gt                3919
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    
;
SUPERFLIP. Palatinus, L.; Chapuis, G. 
J. Appl. Cryst. 2007, 40, 786-790.
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0280P)²+0.9520P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4161
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0239
_refine_ls_wR_factor_ref         0.0576
_refine_ls_wR_factor_gt          0.0565
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0417(4) 0.6738(4) 0.2397(3) 0.0245(7) Uani 1 1 d . . . . .
C2 C 1.0462(4) 0.7415(4) 0.3242(3) 0.0245(7) Uani 1 1 d . . . . .
H2 H 0.9844 0.8210 0.3108 0.029 Uiso 1 1 calc R U . . .
C3 C 1.1425(4) 0.6904(4) 0.4280(3) 0.0259(7) Uani 1 1 d . . . . .
C4 C 1.2332(4) 0.5739(4) 0.4483(3) 0.0273(7) Uani 1 1 d . . . . .
H4 H 1.2979 0.5389 0.5207 0.033 Uiso 1 1 calc R U . . .
C5 C 1.2282(4) 0.5094(4) 0.3617(3) 0.0264(7) Uani 1 1 d . . . . .
C6 C 1.1333(4) 0.5583(4) 0.2562(3) 0.0257(7) Uani 1 1 d . . . . .
H6 H 1.1308 0.5143 0.1967 0.031 Uiso 1 1 calc R U . . .
C7 C 1.1524(4) 0.7604(4) 0.5217(4) 0.0314(8) Uani 1 1 d . . . . .
C8 C 1.3228(5) 0.3818(5) 0.3843(4) 0.0383(9) Uani 1 1 d . . . . .
C9 C 0.6041(5) 0.9466(5) -0.2349(4) 0.0489(11) Uani 1 1 d . . . . .
H9A H 0.6711 0.9301 -0.3018 0.059 Uiso 1 1 calc R U . . .
H9B H 0.6373 1.0360 -0.2323 0.059 Uiso 1 1 calc R U . . .
C10 C 0.4476(5) 0.9582(5) -0.2725(4) 0.0440(10) Uani 1 1 d . . . . .
H10A H 0.4441 0.9896 -0.3718 0.053 Uiso 1 1 calc R U . . .
H10B H 0.3938 1.0286 -0.2488 0.053 Uiso 1 1 calc R U . . .
C11 C 0.3791(4) 0.8099(4) -0.1920(4) 0.0365(8) Uani 1 1 d . . . . .
H11A H 0.3941 0.7518 -0.2428 0.044 Uiso 1 1 calc R U . . .
H11B H 0.2709 0.8150 -0.1712 0.044 Uiso 1 1 calc R U . . .
C12 C 0.4607(4) 0.7466(4) -0.0629(4) 0.0339(8) Uani 1 1 d . . . . .
H12A H 0.4045 0.7614 0.0105 0.041 Uiso 1 1 calc R U . . .
H12B H 0.4745 0.6419 -0.0311 0.041 Uiso 1 1 calc R U . . .
F1 F 1.1240(3) 0.6661(3) 0.6518(2) 0.0533(7) Uani 1 1 d . . . . .
F2 F 1.0593(3) 0.8677(3) 0.4945(3) 0.0587(8) Uani 1 1 d . . . . .
F3 F 1.2894(3) 0.8141(3) 0.5128(2) 0.0465(6) Uani 1 1 d . . . . .
O1 O 0.6052(3) 0.8234(3) -0.0991(2) 0.0257(5) Uani 1 1 d . . . . .
W1 W 0.79858(2) 0.76638(2) 0.03103(2) 0.02236(6) Uani 1 1 d . . . . .
Cl1 Cl 0.61282(10) 0.70330(10) 0.20932(9) 0.03392(19) Uani 1 1 d . . . . .
Cl2 Cl 0.78572(10) 1.00449(9) -0.00493(9) 0.03267(19) Uani 1 1 d . . . . .
Cl3 Cl 0.94272(10) 0.84103(11) -0.17307(9) 0.03396(19) Uani 1 1 d . . . . .
Cl4 Cl 0.76978(11) 0.54179(9) 0.03676(10) 0.0356(2) Uani 1 1 d . . . . .
N1 N 0.9413(3) 0.7186(3) 0.1397(3) 0.0285(6) Uani 1 1 d . . . . .
F4 F 1.4431(3) 0.3778(3) 0.4481(3) 0.0576(7) Uani 1 1 d . . . . .
F5 F 1.3707(5) 0.3823(4) 0.2683(3) 0.0953(14) Uani 1 1 d . . . . .
F6 F 1.2504(4) 0.2598(3) 0.4586(5) 0.0918(13) 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 N1 1.380(4) . ?
C1 C2 1.393(5) . ?
C1 C6 1.397(5) . ?
C2 C3 1.384(5) . ?
C3 C4 1.392(5) . ?
C3 C7 1.507(5) . ?
C4 C5 1.389(5) . ?
C5 C6 1.387(5) . ?
C5 C8 1.499(5) . ?
C7 F2 1.322(4) . ?
C7 F1 1.329(4) . ?
C7 F3 1.337(4) . ?
C8 F6 1.308(5) . ?
C8 F5 1.314(5) . ?
C8 F4 1.318(5) . ?
C9 O1 1.467(4) . ?
C9 C10 1.482(6) . ?
C10 C11 1.502(6) . ?
C11 C12 1.510(5) . ?
C12 O1 1.466(4) . ?
O1 W1 2.231(2) . ?
W1 N1 1.727(3) . ?
W1 Cl3 2.3163(9) . ?
W1 Cl4 2.3187(9) . ?
W1 Cl2 2.3230(9) . ?
W1 Cl1 2.3396(9) . ?

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 C2 119.5(3) . . ?
N1 C1 C6 118.9(3) . . ?
C2 C1 C6 121.6(3) . . ?
C3 C2 C1 118.6(3) . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 C7 120.7(3) . . ?
C4 C3 C7 118.3(3) . . ?
C5 C4 C3 119.4(3) . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 C8 119.0(3) . . ?
C4 C5 C8 119.9(3) . . ?
C5 C6 C1 118.3(3) . . ?
F2 C7 F1 107.6(3) . . ?
F2 C7 F3 106.9(3) . . ?
F1 C7 F3 106.1(3) . . ?
F2 C7 C3 112.9(3) . . ?
F1 C7 C3 111.6(3) . . ?
F3 C7 C3 111.4(3) . . ?
F6 C8 F5 107.8(4) . . ?
F6 C8 F4 106.1(4) . . ?
F5 C8 F4 105.9(4) . . ?
F6 C8 C5 112.0(3) . . ?
F5 C8 C5 111.6(3) . . ?
F4 C8 C5 113.1(3) . . ?
O1 C9 C10 105.8(3) . . ?
C9 C10 C11 105.7(3) . . ?
C10 C11 C12 104.1(3) . . ?
O1 C12 C11 105.5(3) . . ?
C12 O1 C9 109.7(3) . . ?
C12 O1 W1 126.0(2) . . ?
C9 O1 W1 124.3(2) . . ?
N1 W1 O1 176.80(11) . . ?
N1 W1 Cl3 98.18(10) . . ?
O1 W1 Cl3 85.01(6) . . ?
N1 W1 Cl4 95.85(10) . . ?
O1 W1 Cl4 83.90(6) . . ?
Cl3 W1 Cl4 89.10(4) . . ?
N1 W1 Cl2 96.37(10) . . ?
O1 W1 Cl2 83.88(7) . . ?
Cl3 W1 Cl2 89.44(3) . . ?
Cl4 W1 Cl2 167.78(3) . . ?
N1 W1 Cl1 93.31(10) . . ?
O1 W1 Cl1 83.50(7) . . ?
Cl3 W1 Cl1 168.51(3) . . ?
Cl4 W1 Cl1 89.73(3) . . ?
Cl2 W1 Cl1 89.29(3) . . ?
C1 N1 W1 172.9(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
N1 C1 C2 C3 177.0(3) . . . . ?
C6 C1 C2 C3 -1.1(5) . . . . ?
C1 C2 C3 C4 -0.1(5) . . . . ?
C1 C2 C3 C7 179.6(3) . . . . ?
C2 C3 C4 C5 0.9(5) . . . . ?
C7 C3 C4 C5 -178.8(3) . . . . ?
C3 C4 C5 C6 -0.6(5) . . . . ?
C3 C4 C5 C8 -178.7(3) . . . . ?
C4 C5 C6 C1 -0.5(5) . . . . ?
C8 C5 C6 C1 177.6(3) . . . . ?
N1 C1 C6 C5 -176.7(3) . . . . ?
C2 C1 C6 C5 1.4(5) . . . . ?
C2 C3 C7 F2 1.6(5) . . . . ?
C4 C3 C7 F2 -178.7(3) . . . . ?
C2 C3 C7 F1 122.9(4) . . . . ?
C4 C3 C7 F1 -57.4(4) . . . . ?
C2 C3 C7 F3 -118.8(4) . . . . ?
C4 C3 C7 F3 60.9(4) . . . . ?
C6 C5 C8 F6 -84.0(5) . . . . ?
C4 C5 C8 F6 94.1(5) . . . . ?
C6 C5 C8 F5 36.9(5) . . . . ?
C4 C5 C8 F5 -145.0(4) . . . . ?
C6 C5 C8 F4 156.2(4) . . . . ?
C4 C5 C8 F4 -25.7(5) . . . . ?
O1 C9 C10 C11 -24.7(5) . . . . ?
C9 C10 C11 C12 30.8(5) . . . . ?
C10 C11 C12 O1 -25.1(4) . . . . ?
C11 C12 O1 C9 10.4(4) . . . . ?
C11 C12 O1 W1 -170.4(2) . . . . ?
C10 C9 O1 C12 8.8(5) . . . . ?
C10 C9 O1 W1 -170.4(3) . . . . ?

_refine_diff_density_max         1.577
_refine_diff_density_min         -1.239
_refine_diff_density_rms         0.124

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: pentane'
_chemical_properties_physical    ', Air-sensitive,Moisture-sensitive'
####################################################################### 
# 
# 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_024ZRT16
_audit_block_doi                 10.5517/ccdc.csd.cc1mzdss
_database_code_depnum_ccdc_archive 'CCDC 1518776'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7QI00128B 2017
_audit_update_record             
;
2016-11-23 deposited with the CCDC.
2017-05-10 downloaded from the CCDC.
;
#WN-2,6-Me-C6H3Me3Cl_2.3

# start Validation Reply Form
_vrf_PLAT910_024ZRT16            
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min)          22 Note  
RESPONSE: A data collection strategy was chosen to achieve 99% completeness
with twofold redundancy. The theta min limit was set to 4 angstrom during data
processing. It is noted that _cell_measurement_theta_min is 5.097.
;
_vrf_PLAT971_024ZRT16            
;
PROBLEM: Check Calcd Residual Density  0.93A From     C11       2.04 eA-3  
RESPONSE: Q1 is located at 0.3832, -0.1565, 0.7516 (x,y,z) with nearest
non-H atom C11 at 0.90 anstroms. Q2 is located at -0.1591, 0.0527, 0.7384
with nearest non-H atom C3 at 1.22 angstroms. Such residual density  may be 
an effect of twinning (that has not been identifed) or
problems related to absorption (Absorption correction: Multi-scan from 
symmetry-related measurements using Sortav (Blessing 1995)).
;
_vrf_PLAT972_024ZRT16            
;
PROBLEM: Check Calcd Residual Density  0.78A From      W1      -1.82 eA-3  
RESPONSE: 
 Deepest hole   -1.69  at  0.3672  0.4468  0.1828  [  0.81 A from W1 ]
The hole lies within 1 angstrom of the heaviest atom W1.
;
_vrf_PLAT973_024ZRT16            
;
PROBLEM: Check Calcd Positive Residual Density on      W1       1.20 eA-3  
RESPONSE: Such residual density  may be 
an effect of twinning (that has not been identified) or
problems related to absorption (Absorption correction: Multi-scan from 
symmetry-related measurements using Sortav (Blessing 1995)).
;
_vrf_PLAT977_024ZRT16            
;
PROBLEM: Check the Negative Difference Density on     H9C      -0.37 eA-3  
RESPONSE: H9C is one of the three H atoms bound to the methyl C atom C9.
It has been placed using a HFIX 137 command.
;

# end Validation Reply Form

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H18 Cl N W'
_chemical_formula_sum            'C11 H18 Cl N W'
_chemical_formula_weight         383.56

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'
Cl Cl 0.1484 0.1585 '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'
W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   10.4810(2)
_cell_length_b                   10.8951(3)
_cell_length_c                   12.1474(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.4730(10)
_cell_angle_gamma                90
_cell_volume                     1299.51(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    19444
_cell_measurement_theta_min      5.097
_cell_measurement_theta_max      27.485

_exptl_crystal_description       irregular
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.960
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    9.060
_shelx_estimated_absorpt_T_min   0.464
_shelx_estimated_absorpt_T_max   0.660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.708
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
Multi-scan from symmetry-related measurements using
Sortav (Blessing 1995)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            5749
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         5.181
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2964
_reflns_number_gt                2473
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    
;
SHELXS-G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., 2008, 64, 112-122.
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0455P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2964
_refine_ls_number_parameters     132
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0794
_refine_ls_wR_factor_gt          0.0752
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0727(4) 0.1021(4) 0.6384(4) 0.0263(10) Uani 1 1 d . . . . .
C2 C -0.0153(5) 0.0534(4) 0.6903(5) 0.0349(12) Uani 1 1 d . . . . .
C3 C -0.1514(6) 0.0894(5) 0.6461(5) 0.0431(13) Uani 1 1 d . . . . .
H3 H -0.2131 0.0591 0.6812 0.052 Uiso 1 1 calc R U . . .
C4 C -0.1978(5) 0.1694(5) 0.5509(5) 0.0445(14) Uani 1 1 d . . . . .
H4 H -0.2913 0.1919 0.5207 0.053 Uiso 1 1 calc R U . . .
C5 C -0.1102(5) 0.2159(5) 0.5009(4) 0.0394(13) Uani 1 1 d . . . . .
H5 H -0.1436 0.2707 0.4363 0.047 Uiso 1 1 calc R U . . .
C6 C 0.0266(5) 0.1848(4) 0.5422(4) 0.0323(11) Uani 1 1 d . . . . .
C7 C 0.0329(6) -0.0368(5) 0.7915(6) 0.0470(15) Uani 1 1 d . . . . .
H7A H 0.0534 -0.1158 0.7627 0.070 Uiso 1 1 calc R U . . .
H7B H -0.0387 -0.0481 0.8251 0.070 Uiso 1 1 calc R U . . .
H7C H 0.1151 -0.0049 0.8519 0.070 Uiso 1 1 calc R U . . .
C8 C 0.1228(5) 0.2371(5) 0.4878(4) 0.0460(14) Uani 1 1 d . . . . .
H8A H 0.0732 0.2929 0.4239 0.069 Uiso 1 1 calc R U . . .
H8B H 0.1628 0.1703 0.4565 0.069 Uiso 1 1 calc R U . . .
H8C H 0.1954 0.2823 0.5475 0.069 Uiso 1 1 calc R U . . .
C9 C 0.3917(6) 0.2072(5) 0.8591(5) 0.0405(13) Uani 1 1 d . . . . .
H9A H 0.3134 0.2602 0.8198 0.061 Uiso 1 1 calc R U . . .
H9B H 0.4761 0.2528 0.8710 0.061 Uiso 1 1 calc R U . . .
H9C H 0.3887 0.1809 0.9353 0.061 Uiso 1 1 calc R U . . .
C10 C 0.4403(5) 0.0648(4) 0.6047(4) 0.0324(11) Uani 1 1 d . . . . .
H10A H 0.3581 0.0691 0.5343 0.049 Uiso 1 1 calc R U . . .
H10B H 0.4938 -0.0074 0.5999 0.049 Uiso 1 1 calc R U . . .
H10C H 0.4950 0.1391 0.6100 0.049 Uiso 1 1 calc R U . . .
C11 C 0.3683(6) -0.1250(5) 0.8149(5) 0.0404(12) Uani 1 1 d . . . . .
H11A H 0.3755 -0.1206 0.8974 0.061 Uiso 1 1 calc R U . . .
H11B H 0.4416 -0.1768 0.8081 0.061 Uiso 1 1 calc R U . . .
H11C H 0.2800 -0.1603 0.7680 0.061 Uiso 1 1 calc R U . . .
Cl1 Cl 0.62694(14) 0.03487(14) 0.86715(13) 0.0458(4) Uani 1 1 d . . . . .
N1 N 0.2100(4) 0.0717(3) 0.6832(3) 0.0259(9) Uani 1 1 d . . . . .
W1 W 0.38507(2) 0.05149(2) 0.75354(2) 0.02466(10) 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 N1 1.389(6) . ?
C1 C2 1.392(7) . ?
C1 C6 1.419(7) . ?
C2 C3 1.393(8) . ?
C2 C7 1.516(7) . ?
C3 C4 1.392(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.364(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(7) . ?
C5 H5 0.9500 . ?
C6 C8 1.498(7) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 W1 2.113(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 W1 2.088(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 W1 2.092(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
Cl1 W1 2.4324(14) . ?
N1 W1 1.746(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
N1 C1 C2 119.4(4) . . ?
N1 C1 C6 118.8(4) . . ?
C2 C1 C6 121.7(4) . . ?
C1 C2 C3 118.0(5) . . ?
C1 C2 C7 121.9(5) . . ?
C3 C2 C7 120.1(5) . . ?
C4 C3 C2 120.7(5) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 120.5(5) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 121.4(5) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 117.7(5) . . ?
C5 C6 C8 121.2(5) . . ?
C1 C6 C8 121.1(4) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
W1 C9 H9A 109.5 . . ?
W1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
W1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
W1 C10 H10A 109.5 . . ?
W1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
W1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
W1 C11 H11A 109.5 . . ?
W1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
W1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 N1 W1 171.7(3) . . ?
N1 W1 C10 97.5(2) . . ?
N1 W1 C11 94.90(19) . . ?
C10 W1 C11 117.1(2) . . ?
N1 W1 C9 90.08(19) . . ?
C10 W1 C9 120.6(2) . . ?
C11 W1 C9 120.7(2) . . ?
N1 W1 Cl1 174.45(13) . . ?
C10 W1 Cl1 86.95(15) . . ?
C11 W1 Cl1 85.99(16) . . ?
C9 W1 Cl1 84.77(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
N1 C1 C2 C3 177.6(4) . . . . ?
C6 C1 C2 C3 -0.8(7) . . . . ?
N1 C1 C2 C7 -2.8(7) . . . . ?
C6 C1 C2 C7 178.8(5) . . . . ?
C1 C2 C3 C4 1.5(8) . . . . ?
C7 C2 C3 C4 -178.1(5) . . . . ?
C2 C3 C4 C5 -1.3(8) . . . . ?
C3 C4 C5 C6 0.3(8) . . . . ?
C4 C5 C6 C1 0.4(7) . . . . ?
C4 C5 C6 C8 -179.3(5) . . . . ?
N1 C1 C6 C5 -178.5(4) . . . . ?
C2 C1 C6 C5 -0.1(7) . . . . ?
N1 C1 C6 C8 1.2(7) . . . . ?
C2 C1 C6 C8 179.6(5) . . . . ?

_refine_diff_density_max         2.281
_refine_diff_density_min         -1.692
_refine_diff_density_rms         0.183

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
_chemical_properties_physical    ', Air-sensitive,Moisture-sensitive'
####################################################################### 
# 
# 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_032zrt16
_audit_block_doi                 10.5517/ccdc.csd.cc1mzdnn
_database_code_depnum_ccdc_archive 'CCDC 1518772'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7QI00128B 2017
_audit_update_record             
;
2016-11-23 deposited with the CCDC.
2017-05-10 downloaded from the CCDC.
;
#WN-2,6-F-C6H3-Cl4thf_1.5

# start Validation Reply Form
_vrf_PLAT977_032zrt16            
;
PROBLEM: Check the Negative Difference Density on     H8A      -0.41 eA-3  
RESPONSE: H8A and H9A are H atoms bound to the methylene C atoms, C8 and C9
respectively. They were placed using HFIX 23. Visual inspection of
the thermal ellipsoids of C8 and C9 show them to be elongated, as expected
from the movement of the tetrahydrofuran group.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H11 Cl4 F2 N O W'
_chemical_formula_sum            'C10 H11 Cl4 F2 N O W'
_chemical_formula_weight         524.85

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1651(2)
_cell_length_b                   9.4012(3)
_cell_length_c                   9.9731(3)
_cell_angle_alpha                87.462(2)
_cell_angle_beta                 86.122(2)
_cell_angle_gamma                79.773(2)
_cell_volume                     751.26(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    12717
_cell_measurement_theta_min      3.7990
_cell_measurement_theta_max      30.2240

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.320
_exptl_crystal_F_000             492
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.096
_exptl_absorpt_coefficient_mu    8.410
_shelx_estimated_absorpt_T_min   0.266
_shelx_estimated_absorpt_T_max   0.499
_exptl_absorpt_correction_T_min  0.55541
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      150(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.4102
_diffrn_reflns_number            15868
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.958
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3447
_reflns_number_gt                3325
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    
;
Superflip L. Palatinus and G. Chapuis,  
J. Appl. Crystallogr., 2007, 40, 786-790.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Ortep III for windows
L. J. Farrugia, J. Appl. Crystallogr., 1997, 30, 565.
;
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0188P)²+0.3739P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3447
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0167
_refine_ls_R_factor_gt           0.0156
_refine_ls_wR_factor_ref         0.0385
_refine_ls_wR_factor_gt          0.0379
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
W1 W 0.24008(2) 0.13057(2) 0.74482(2) 0.01672(4) Uani 1 1 d . . . . .
Cl1 Cl 0.20432(9) 0.17790(8) 0.97383(6) 0.03024(15) Uani 1 1 d . . . . .
Cl2 Cl 0.29052(7) 0.03299(7) 0.53371(6) 0.01946(12) Uani 1 1 d . . . . .
Cl3 Cl -0.02427(7) 0.06724(7) 0.75715(6) 0.02150(12) Uani 1 1 d . . . . .
Cl4 Cl 0.52147(8) 0.14353(8) 0.75157(7) 0.02721(14) Uani 1 1 d . . . . .
F1 F 0.3621(2) 0.41479(18) 0.48143(18) 0.0377(4) Uani 1 1 d . . . . .
F2 F -0.0814(2) 0.49113(19) 0.80752(19) 0.0445(5) Uani 1 1 d . . . . .
O1 O 0.3232(2) -0.0991(2) 0.81531(17) 0.0214(4) Uani 1 1 d . . . . .
N1 N 0.1807(3) 0.3071(2) 0.6893(2) 0.0212(4) Uani 1 1 d . . . . .
C1 C 0.1433(3) 0.4499(3) 0.6472(2) 0.0192(5) Uani 1 1 d . . . . .
C2 C 0.2370(3) 0.5072(3) 0.5423(3) 0.0229(5) Uani 1 1 d . . . . .
C3 C 0.2048(3) 0.6498(3) 0.5024(3) 0.0273(6) Uani 1 1 d . . . . .
H3 H 0.2710 0.6862 0.4314 0.033 Uiso 1 1 calc R U . . .
C4 C 0.0743(3) 0.7400(3) 0.5672(3) 0.0251(5) Uani 1 1 d . . . . .
H4 H 0.0514 0.8394 0.5404 0.030 Uiso 1 1 calc R U . . .
C5 C -0.0237(3) 0.6885(3) 0.6704(3) 0.0297(6) Uani 1 1 d . . . . .
H5 H -0.1136 0.7515 0.7138 0.036 Uiso 1 1 calc R U . . .
C6 C 0.0113(3) 0.5450(3) 0.7087(3) 0.0248(6) Uani 1 1 d . . . . .
C7 C 0.2450(4) -0.1716(4) 0.9288(3) 0.0388(7) Uani 1 1 d . . . . .
H7A H 0.1276 -0.1751 0.9124 0.047 Uiso 1 1 calc R U . . .
H7B H 0.2472 -0.1193 1.0125 0.047 Uiso 1 1 calc R U . . .
C8 C 0.3425(5) -0.3196(4) 0.9406(4) 0.0558(10) Uani 1 1 d . . . . .
H8A H 0.3989 -0.3326 1.0262 0.067 Uiso 1 1 calc R U . . .
H8B H 0.2676 -0.3916 0.9397 0.067 Uiso 1 1 calc R U . . .
C9 C 0.4652(5) -0.3397(4) 0.8275(4) 0.0494(9) Uani 1 1 d . . . . .
H9A H 0.4321 -0.4036 0.7617 0.059 Uiso 1 1 calc R U . . .
H9B H 0.5756 -0.3849 0.8588 0.059 Uiso 1 1 calc R U . . .
C10 C 0.4734(4) -0.1960(3) 0.7647(3) 0.0321(6) Uani 1 1 d . . . . .
H10A H 0.5747 -0.1617 0.7895 0.038 Uiso 1 1 calc R U . . .
H10B H 0.4761 -0.2001 0.6655 0.038 Uiso 1 1 calc R 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
W1 N1 1.722(2) . ?
W1 O1 2.2419(18) . ?
W1 Cl2 2.3160(6) . ?
W1 Cl4 2.3279(6) . ?
W1 Cl3 2.3329(6) . ?
W1 Cl1 2.3352(6) . ?
F1 C2 1.347(3) . ?
F2 C6 1.339(3) . ?
O1 C10 1.466(3) . ?
O1 C7 1.463(3) . ?
N1 C1 1.376(3) . ?
C1 C6 1.397(4) . ?
C1 C2 1.400(4) . ?
C2 C3 1.366(4) . ?
C3 C4 1.381(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.371(4) . ?
C5 H5 0.9500 . ?
C7 C8 1.479(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.453(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.474(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 W1 O1 178.73(8) . . ?
N1 W1 Cl2 96.26(7) . . ?
O1 W1 Cl2 83.28(5) . . ?
N1 W1 Cl4 95.28(7) . . ?
O1 W1 Cl4 83.55(5) . . ?
Cl2 W1 Cl4 90.13(2) . . ?
N1 W1 Cl3 97.07(7) . . ?
O1 W1 Cl3 84.12(5) . . ?
Cl2 W1 Cl3 89.28(2) . . ?
Cl4 W1 Cl3 167.64(2) . . ?
N1 W1 Cl1 95.94(7) . . ?
O1 W1 Cl1 84.54(5) . . ?
Cl2 W1 Cl1 167.80(2) . . ?
Cl4 W1 Cl1 89.16(2) . . ?
Cl3 W1 Cl1 88.81(2) . . ?
C10 O1 C7 108.8(2) . . ?
C10 O1 W1 125.74(15) . . ?
C7 O1 W1 125.15(16) . . ?
C1 N1 W1 176.22(18) . . ?
N1 C1 C6 121.5(2) . . ?
N1 C1 C2 121.6(2) . . ?
C6 C1 C2 116.9(2) . . ?
F1 C2 C3 120.9(2) . . ?
F1 C2 C1 116.8(2) . . ?
C3 C2 C1 122.2(2) . . ?
C2 C3 C4 118.8(3) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 118.8(3) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
F2 C6 C5 120.5(2) . . ?
F2 C6 C1 117.6(2) . . ?
C5 C6 C1 121.9(3) . . ?
O1 C7 C8 106.6(2) . . ?
O1 C7 H7A 110.4 . . ?
C8 C7 H7A 110.4 . . ?
O1 C7 H7B 110.4 . . ?
C8 C7 H7B 110.4 . . ?
H7A C7 H7B 108.6 . . ?
C9 C8 C7 108.2(3) . . ?
C9 C8 H8A 110.1 . . ?
C7 C8 H8A 110.1 . . ?
C9 C8 H8B 110.1 . . ?
C7 C8 H8B 110.1 . . ?
H8A C8 H8B 108.4 . . ?
C8 C9 C10 107.5(3) . . ?
C8 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
C8 C9 H9B 110.2 . . ?
C10 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
O1 C10 C9 106.4(2) . . ?
O1 C10 H10A 110.5 . . ?
C9 C10 H10A 110.5 . . ?
O1 C10 H10B 110.5 . . ?
C9 C10 H10B 110.5 . . ?
H10A C10 H10B 108.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 F1 2.2(4) . . . . ?
C6 C1 C2 F1 -178.8(2) . . . . ?
N1 C1 C2 C3 -177.8(2) . . . . ?
C6 C1 C2 C3 1.3(4) . . . . ?
F1 C2 C3 C4 179.5(2) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 F2 -179.6(2) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
N1 C1 C6 F2 -2.2(4) . . . . ?
C2 C1 C6 F2 178.7(2) . . . . ?
N1 C1 C6 C5 177.9(2) . . . . ?
C2 C1 C6 C5 -1.2(4) . . . . ?
C10 O1 C7 C8 -4.4(4) . . . . ?
W1 O1 C7 C8 -178.7(2) . . . . ?
O1 C7 C8 C9 -5.9(4) . . . . ?
C7 C8 C9 C10 13.8(5) . . . . ?
C7 O1 C10 C9 12.7(3) . . . . ?
W1 O1 C10 C9 -173.0(2) . . . . ?
C8 C9 C10 O1 -16.3(4) . . . . ?

_refine_diff_density_max         0.611
_refine_diff_density_min         -0.882
_refine_diff_density_rms         0.095

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
_chemical_properties_physical    ', Air-sensitive,Moisture-sensitive'
####################################################################### 
# 
# 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_007cw16
_audit_block_doi                 10.5517/ccdc.csd.cc1mzdmm
_database_code_depnum_ccdc_archive 'CCDC 1518771'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7QI00128B 2017
_audit_update_record             
;
2016-11-23 deposited with the CCDC.
2017-05-10 downloaded from the CCDC.
;
#WNPhCl4thf_1.4

# start Validation Reply Form
_vrf_PLAT910_007cw16             
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min)          21 Note  
RESPONSE: A data collection strategy was chosen to achieve 99% completeness
with twofold redundancy. The theta min limit was set to 4 angstrom during data
processing. It is noted that _cell_measurement_theta_min is 5.097.
;
_vrf_PLAT241_007cw16             
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of         C7 Check 
RESPONSE: C7 is part of the metal bound tetrahydofuran group, and it bound to 
O1 (the thermal ellipsoid of which indicates little thermal motion) and C8.
Visual inspection of the C7 ellipsoid shows it to be elongated, in keeping
with the expected motion of the tetrahydrofuran ring.
;
_vrf_PLAT242_007cw16             
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         O1 Check 
RESPONSE: O1 is part of the metal bound tetrahydofuran group, and it bound to 
W1 and C7/C10 (the thermal ellipsoids of which are elongated, in keeping with
the expected motion of the tetrahydrofuran group)
Visual inspection of the O1 ellipsoid shows that it is not elongated.
;
_vrf_PLAT971_007cw16             
;
PROBLEM: Check Calcd Residual Density  1.21A From      W1       1.79 eA-3  
RESPONSE: 
Highest peak    2.24  at  0.7616  0.1076  0.9576  [  1.37 A from W1 ]
The largest q peaks are all concentrated around W1 within 1.5 angstrom.

;
_vrf_PLAT977_007cw16             
;
PROBLEM: Check the Negative Difference Density on     H7A      -0.62 eA-3  
RESPONSE: H7A, H8A and H9A are one of two methylene protons bound to C7, C8 and C9 
respectively (part of the metal-bound tetrahydrofuran ring. 
The H atoms have been placed using HFIX 23.
;

# end Validation Reply Form

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H13 Cl4 N O W'
_chemical_formula_sum            'C10 H13 Cl4 N O W'
_chemical_formula_weight         488.86

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'
Cl Cl 0.1484 0.1585 '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'
W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   14.7317(3)
_cell_length_b                   7.18890(10)
_cell_length_c                   13.9923(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.1200(10)
_cell_angle_gamma                90
_cell_volume                     1448.82(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    19543
_cell_measurement_theta_min      5.097
_cell_measurement_theta_max      27.485

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.241
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    8.693
_shelx_estimated_absorpt_T_min   0.180
_shelx_estimated_absorpt_T_max   0.275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            6016
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         5.106
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3314
_reflns_number_gt                2812
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       KappaCCD
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_structure_solution    superflip
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'Ortep III, L. J. Farrugia, J. Appl. Crystallogr., 1997, 30, 565.'
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0409P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3314
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0744
_refine_ls_wR_factor_gt          0.0708
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
W1 W 0.24043(2) 0.70180(2) 0.04364(2) 0.02207(8) Uani 1 1 d . . . . .
Cl1 Cl 0.28699(8) 0.85895(18) 0.19158(8) 0.0317(3) Uani 1 1 d . . . . .
Cl2 Cl 0.35550(8) 0.47976(17) 0.09269(8) 0.0321(3) Uani 1 1 d . . . . .
Cl3 Cl 0.17312(8) 0.51305(17) -0.08845(8) 0.0325(3) Uani 1 1 d . . . . .
Cl4 Cl 0.10493(8) 0.87925(17) 0.01247(9) 0.0344(3) Uani 1 1 d . . . . .
O1 O 0.1613(2) 0.5229(4) 0.1278(2) 0.0275(7) Uani 1 1 d . . . . .
N1 N 0.3038(3) 0.8349(5) -0.0206(3) 0.0266(8) Uani 1 1 d . . . . .
C1 C 0.3588(3) 0.9365(6) -0.0707(3) 0.0233(9) Uani 1 1 d . . . . .
C2 C 0.3373(3) 1.1225(7) -0.0930(3) 0.0301(10) Uani 1 1 d . . . . .
H2 H 0.2839 1.1776 -0.0766 0.036 Uiso 1 1 calc R U . . .
C3 C 0.3947(4) 1.2257(7) -0.1393(4) 0.0353(12) Uani 1 1 d . . . . .
H3 H 0.3809 1.3524 -0.1554 0.042 Uiso 1 1 calc R U . . .
C4 C 0.4730(3) 1.1428(8) -0.1621(3) 0.0338(11) Uani 1 1 d . . . . .
H4 H 0.5127 1.2140 -0.1933 0.041 Uiso 1 1 calc R U . . .
C5 C 0.4934(3) 0.9590(7) -0.1400(3) 0.0308(11) Uani 1 1 d . . . . .
H5 H 0.5469 0.9039 -0.1561 0.037 Uiso 1 1 calc R U . . .
C6 C 0.4363(3) 0.8547(7) -0.0943(3) 0.0272(10) Uani 1 1 d . . . . .
H6 H 0.4501 0.7276 -0.0791 0.033 Uiso 1 1 calc R U . . .
C7 C 0.1501(6) 0.3208(8) 0.1158(6) 0.066(2) Uani 1 1 d . . . . .
H7A H 0.1105 0.2913 0.0513 0.079 Uiso 1 1 calc R U . . .
H7B H 0.2113 0.2607 0.1202 0.079 Uiso 1 1 calc R U . . .
C8 C 0.1074(6) 0.2547(9) 0.1928(5) 0.060(2) Uani 1 1 d . . . . .
H8A H 0.1521 0.1777 0.2391 0.073 Uiso 1 1 calc R U . . .
H8B H 0.0529 0.1768 0.1650 0.073 Uiso 1 1 calc R U . . .
C9 C 0.0785(4) 0.4141(9) 0.2441(4) 0.0479(15) Uani 1 1 d . . . . .
H9A H 0.1065 0.4068 0.3148 0.057 Uiso 1 1 calc R U . . .
H9B H 0.0101 0.4155 0.2358 0.057 Uiso 1 1 calc R U . . .
C10 C 0.1104(5) 0.5841(8) 0.2013(5) 0.0564(18) Uani 1 1 d . . . . .
H10A H 0.0566 0.6619 0.1708 0.068 Uiso 1 1 calc R U . . .
H10B H 0.1512 0.6582 0.2526 0.068 Uiso 1 1 calc R 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
W1 N1 1.717(4) . ?
W1 O1 2.230(3) . ?
W1 Cl2 2.3246(11) . ?
W1 Cl1 2.3314(11) . ?
W1 Cl4 2.3317(11) . ?
W1 Cl3 2.3390(11) . ?
O1 C10 1.463(6) . ?
O1 C7 1.468(6) . ?
N1 C1 1.385(6) . ?
C1 C6 1.385(6) . ?
C1 C2 1.394(6) . ?
C2 C3 1.385(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(7) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.437(8) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.462(9) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.480(8) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 W1 O1 178.40(15) . . ?
N1 W1 Cl2 95.43(13) . . ?
O1 W1 Cl2 82.98(9) . . ?
N1 W1 Cl1 95.97(13) . . ?
O1 W1 Cl1 84.24(8) . . ?
Cl2 W1 Cl1 90.59(4) . . ?
N1 W1 Cl4 97.77(13) . . ?
O1 W1 Cl4 83.82(9) . . ?
Cl2 W1 Cl4 166.77(5) . . ?
Cl1 W1 Cl4 88.95(4) . . ?
N1 W1 Cl3 95.53(13) . . ?
O1 W1 Cl3 84.30(8) . . ?
Cl2 W1 Cl3 89.82(4) . . ?
Cl1 W1 Cl3 168.40(4) . . ?
Cl4 W1 Cl3 88.01(4) . . ?
C10 O1 C7 108.4(4) . . ?
C10 O1 W1 126.9(3) . . ?
C7 O1 W1 124.7(3) . . ?
C1 N1 W1 177.1(3) . . ?
C6 C1 N1 119.7(4) . . ?
C6 C1 C2 121.0(4) . . ?
N1 C1 C2 119.3(4) . . ?
C3 C2 C1 119.1(5) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 119.6(5) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.8(5) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.0(5) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 119.5(5) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C8 C7 O1 107.3(5) . . ?
C8 C7 H7A 110.2 . . ?
O1 C7 H7A 110.2 . . ?
C8 C7 H7B 110.2 . . ?
O1 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
C7 C8 C9 109.1(5) . . ?
C7 C8 H8A 109.9 . . ?
C9 C8 H8A 109.9 . . ?
C7 C8 H8B 109.9 . . ?
C9 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C8 C9 C10 107.4(5) . . ?
C8 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
C8 C9 H9B 110.2 . . ?
C10 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
O1 C10 C9 106.8(5) . . ?
O1 C10 H10A 110.4 . . ?
C9 C10 H10A 110.4 . . ?
O1 C10 H10B 110.4 . . ?
C9 C10 H10B 110.4 . . ?
H10A C10 H10B 108.6 . . ?

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
C6 C1 C2 C3 0.0(7) . . . . ?
N1 C1 C2 C3 177.2(4) . . . . ?
C1 C2 C3 C4 -0.4(7) . . . . ?
C2 C3 C4 C5 0.6(7) . . . . ?
C3 C4 C5 C6 -0.2(7) . . . . ?
C4 C5 C6 C1 -0.2(6) . . . . ?
N1 C1 C6 C5 -176.9(4) . . . . ?
C2 C1 C6 C5 0.4(6) . . . . ?
C10 O1 C7 C8 -10.0(9) . . . . ?
W1 O1 C7 C8 171.3(5) . . . . ?
O1 C7 C8 C9 8.6(9) . . . . ?
C7 C8 C9 C10 -4.0(9) . . . . ?
C7 O1 C10 C9 7.5(7) . . . . ?
W1 O1 C10 C9 -173.8(4) . . . . ?
C8 C9 C10 O1 -2.3(8) . . . . ?

_refine_diff_density_max         2.237
_refine_diff_density_min         -1.450
_refine_diff_density_rms         0.173

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
_chemical_properties_physical    ', Air-sensitive,Moisture-sensitive'
####################################################################### 
# 
# 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_004CW15
_audit_block_doi                 10.5517/ccdc.csd.cc1mzdkk
_database_code_depnum_ccdc_archive 'CCDC 1518769'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7QI00128B 2017
_audit_update_record             
;
2016-11-23 deposited with the CCDC.
2017-05-10 downloaded from the CCDC.
;
#WN-2,4,6-MeC6H2Cl4thf_1.2

# start Validation Reply Form
_vrf_PLAT910_004CW15             
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min)          25 Note  
RESPONSE: A data collection strategy was chosen to achieve 99% completeness
with twofold redundancy. The theta min limit was set to 4 angstrom during data
processing. It is noted that _cell_measurement_theta_min is 5.
;
_vrf_PLAT971_004CW15             
;
PROBLEM: Check Calcd Residual Density  1.89A From     Cl4       1.52 eA-3  
RESPONSE: 
Highest peak    1.71  at  0.4726  0.6614  0.3650  [1.92 A from CL4]. This
corresponds to Q1 and is located near a heavy Cl ligand. The position
makes it  unlikely to be unassigned/incorrectly assigned electron
density. The remaining Q peaks are located aronund the WCL4NO core of the 
molecule.
;
_vrf_PLAT972_004CW15             
;
PROBLEM: Check Calcd Residual Density  0.84A From      W1      -1.62 eA-3  
RESPONSE: 
Deepest hole   -1.72  at  0.2516  0.0207  0.2425  [  0.79 A from W1 ]
;
_vrf_PLAT977_004CW15             
;
PROBLEM: Check the Negative Difference Density on     H7A      -0.39 eA-3  
RESPONSE: The H atoms (H7A, H7B and H7C) bound to the methyl C7 have been placed
using a AFIX 137 command, where they are placed as an idealised methyl
group with the torsion angle determined from electron density.
;
# end Validation Reply Form


_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H19 Cl4 N O W'
_chemical_formula_sum            'C13 H19 Cl4 N O W'
_chemical_formula_weight         530.94

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'
Cl Cl 0.1484 0.1585 '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'
W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.83670(10)
_cell_length_b                   8.7690(2)
_cell_length_c                   14.2277(3)
_cell_angle_alpha                78.9400(10)
_cell_angle_beta                 89.8440(10)
_cell_angle_gamma                63.8830(10)
_cell_volume                     857.88(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3883
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.055
_exptl_crystal_F_000             508
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    7.350
_shelx_estimated_absorpt_T_min   0.157
_shelx_estimated_absorpt_T_max   0.867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.744
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7214
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         5.110
_diffrn_reflns_theta_max         27.540
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3936
_reflns_number_gt                3594
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    
;
SIR-92
Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A. 
J. Appl. Cryst. 1994, 27, 435.
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
ORTEP-III
Farrugia, L. J. J. Appl. Cryst. 1997, 30, 565.
;
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0333P)²+0.3802P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3936
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0679
_refine_ls_wR_factor_gt          0.0657
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0416(5) 0.4116(5) 0.3175(3) 0.0210(8) Uani 1 1 d . . . . .
C2 C -0.1747(5) 0.3986(5) 0.3815(3) 0.0236(8) Uani 1 1 d . . . . .
C3 C -0.2553(6) 0.5280(6) 0.4334(3) 0.0265(9) Uani 1 1 d . . . . .
H3 H -0.3430 0.5207 0.4781 0.032 Uiso 1 1 calc R U . . .
C4 C -0.2123(6) 0.6688(6) 0.4223(3) 0.0263(9) Uani 1 1 d . . . . .
C5 C -0.0849(6) 0.6779(5) 0.3574(3) 0.0286(9) Uani 1 1 d . . . . .
H5 H -0.0561 0.7739 0.3492 0.034 Uiso 1 1 calc R U . . .
C6 C 0.0035(6) 0.5526(5) 0.3032(3) 0.0266(9) Uani 1 1 d . . . . .
C7 C -0.2229(6) 0.2490(6) 0.3925(3) 0.0314(10) Uani 1 1 d . . . . .
H7A H -0.3194 0.2625 0.4384 0.047 Uiso 1 1 calc R U . . .
H7B H -0.1078 0.1401 0.4163 0.047 Uiso 1 1 calc R U . . .
H7C H -0.2730 0.2467 0.3300 0.047 Uiso 1 1 calc R U . . .
C8 C -0.3026(6) 0.8072(6) 0.4796(3) 0.0347(11) Uani 1 1 d . . . . .
H8A H -0.2099 0.8469 0.4962 0.052 Uiso 1 1 calc R U . . .
H8B H -0.3430 0.7596 0.5387 0.052 Uiso 1 1 calc R U . . .
H8C H -0.4140 0.9054 0.4414 0.052 Uiso 1 1 calc R U . . .
C9 C 0.1440(8) 0.5658(7) 0.2334(4) 0.0437(13) Uani 1 1 d . . . . .
H9A H 0.1516 0.6750 0.2311 0.066 Uiso 1 1 calc R U . . .
H9B H 0.1016 0.5632 0.1692 0.066 Uiso 1 1 calc R U . . .
H9C H 0.2700 0.4677 0.2545 0.066 Uiso 1 1 calc R U . . .
C10 C 0.2948(8) -0.1260(7) 0.0453(4) 0.0456(14) Uani 1 1 d . . . . .
H10A H 0.3069 -0.0369 -0.0049 0.055 Uiso 1 1 calc R U . . .
H10B H 0.1610 -0.1081 0.0403 0.055 Uiso 1 1 calc R U . . .
C11 C 0.4256(7) -0.3022(7) 0.0318(4) 0.0443(13) Uani 1 1 d . . . . .
H11A H 0.4945 -0.2949 -0.0260 0.053 Uiso 1 1 calc R U . . .
H11B H 0.3534 -0.3681 0.0240 0.053 Uiso 1 1 calc R U . . .
C12 C 0.5641(7) -0.3898(6) 0.1210(3) 0.0338(10) Uani 1 1 d . . . . .
H12A H 0.5307 -0.4732 0.1644 0.041 Uiso 1 1 calc R U . . .
H12B H 0.6962 -0.4524 0.1041 0.041 Uiso 1 1 calc R U . . .
C13 C 0.5442(6) -0.2429(6) 0.1677(3) 0.0322(10) Uani 1 1 d . . . . .
H13A H 0.5684 -0.2821 0.2385 0.039 Uiso 1 1 calc R U . . .
H13B H 0.6344 -0.1963 0.1438 0.039 Uiso 1 1 calc R U . . .
Cl1 Cl -0.07825(14) 0.05872(14) 0.17314(8) 0.0280(2) Uani 1 1 d . . . . .
Cl2 Cl 0.12618(17) 0.28279(14) 0.05747(8) 0.0344(2) Uani 1 1 d . . . . .
Cl3 Cl 0.47240(14) 0.10920(14) 0.23379(9) 0.0315(2) Uani 1 1 d . . . . .
Cl4 Cl 0.25959(14) -0.11256(13) 0.34826(7) 0.0260(2) Uani 1 1 d . . . . .
N1 N 0.0513(5) 0.2788(4) 0.2695(2) 0.0224(7) Uani 1 1 d . . . . .
O1 O 0.3460(4) -0.1116(4) 0.1395(2) 0.0245(6) Uani 1 1 d . . . . .
W1 W 0.17740(2) 0.11085(2) 0.21175(2) 0.01920(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.382(5) . ?
C1 C6 1.408(6) . ?
C1 C2 1.410(6) . ?
C2 C3 1.385(6) . ?
C2 C7 1.498(6) . ?
C3 C4 1.398(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(6) . ?
C4 C8 1.503(6) . ?
C5 C6 1.391(6) . ?
C5 H5 0.9500 . ?
C6 C9 1.508(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 O1 1.445(5) . ?
C10 C11 1.481(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.509(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.508(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O1 1.467(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
Cl1 W1 2.3309(10) . ?
Cl2 W1 2.3356(11) . ?
Cl3 W1 2.3272(10) . ?
Cl4 W1 2.3369(10) . ?
N1 W1 1.732(3) . ?
O1 W1 2.258(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
N1 C1 C6 119.1(4) . . ?
N1 C1 C2 118.7(4) . . ?
C6 C1 C2 122.2(4) . . ?
C3 C2 C1 117.1(4) . . ?
C3 C2 C7 122.3(4) . . ?
C1 C2 C7 120.6(4) . . ?
C2 C3 C4 122.4(4) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C5 C4 C3 118.3(4) . . ?
C5 C4 C8 120.6(4) . . ?
C3 C4 C8 121.1(4) . . ?
C4 C5 C6 122.8(4) . . ?
C4 C5 H5 118.6 . . ?
C6 C5 H5 118.6 . . ?
C5 C6 C1 117.1(4) . . ?
C5 C6 C9 121.4(4) . . ?
C1 C6 C9 121.5(4) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 C11 107.8(4) . . ?
O1 C10 H10A 110.1 . . ?
C11 C10 H10A 110.1 . . ?
O1 C10 H10B 110.1 . . ?
C11 C10 H10B 110.1 . . ?
H10A C10 H10B 108.5 . . ?
C10 C11 C12 106.3(4) . . ?
C10 C11 H11A 110.5 . . ?
C12 C11 H11A 110.5 . . ?
C10 C11 H11B 110.5 . . ?
C12 C11 H11B 110.5 . . ?
H11A C11 H11B 108.7 . . ?
C13 C12 C11 104.5(4) . . ?
C13 C12 H12A 110.9 . . ?
C11 C12 H12A 110.9 . . ?
C13 C12 H12B 110.9 . . ?
C11 C12 H12B 110.9 . . ?
H12A C12 H12B 108.9 . . ?
O1 C13 C12 104.2(3) . . ?
O1 C13 H13A 110.9 . . ?
C12 C13 H13A 110.9 . . ?
O1 C13 H13B 110.9 . . ?
C12 C13 H13B 110.9 . . ?
H13A C13 H13B 108.9 . . ?
C1 N1 W1 177.4(3) . . ?
C10 O1 C13 106.9(3) . . ?
C10 O1 W1 125.4(2) . . ?
C13 O1 W1 126.2(2) . . ?
N1 W1 O1 178.75(12) . . ?
N1 W1 Cl3 96.44(11) . . ?
O1 W1 Cl3 82.93(8) . . ?
N1 W1 Cl1 96.76(11) . . ?
O1 W1 Cl1 83.86(8) . . ?
Cl3 W1 Cl1 166.78(4) . . ?
N1 W1 Cl2 96.80(12) . . ?
O1 W1 Cl2 84.29(8) . . ?
Cl3 W1 Cl2 90.19(4) . . ?
Cl1 W1 Cl2 88.76(4) . . ?
N1 W1 Cl4 95.97(12) . . ?
O1 W1 Cl4 82.95(8) . . ?
Cl3 W1 Cl4 89.81(4) . . ?
Cl1 W1 Cl4 88.31(4) . . ?
Cl2 W1 Cl4 167.14(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
N1 C1 C2 C3 175.6(3) . . . . ?
C6 C1 C2 C3 -2.5(6) . . . . ?
N1 C1 C2 C7 -3.7(6) . . . . ?
C6 C1 C2 C7 178.2(4) . . . . ?
C1 C2 C3 C4 1.5(6) . . . . ?
C7 C2 C3 C4 -179.2(4) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C2 C3 C4 C8 179.9(4) . . . . ?
C3 C4 C5 C6 -0.5(6) . . . . ?
C8 C4 C5 C6 179.5(4) . . . . ?
C4 C5 C6 C1 -0.4(6) . . . . ?
C4 C5 C6 C9 -179.4(4) . . . . ?
N1 C1 C6 C5 -176.2(4) . . . . ?
C2 C1 C6 C5 1.9(6) . . . . ?
N1 C1 C6 C9 2.8(6) . . . . ?
C2 C1 C6 C9 -179.1(4) . . . . ?
O1 C10 C11 C12 -2.6(6) . . . . ?
C10 C11 C12 C13 -16.7(6) . . . . ?
C11 C12 C13 O1 29.6(5) . . . . ?
C11 C10 O1 C13 21.8(6) . . . . ?
C11 C10 O1 W1 -171.3(3) . . . . ?
C12 C13 O1 C10 -32.0(5) . . . . ?
C12 C13 O1 W1 161.2(3) . . . . ?

_refine_diff_density_max         1.707
_refine_diff_density_min         -1.715
_refine_diff_density_rms         0.159

_shelxl_version_number           2014-3

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
_chemical_properties_physical    ', Air-sensitive,Moisture-sensitive'
