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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_dwb1239a
_audit_creation_date             2012-05-29
_audit_creation_method           
;
  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_chemical_formula_moiety         'C7 H F4 I O2'
_chemical_formula_sum            'C7 H F4 I O2'
_chemical_formula_weight         319.98
_chemical_absolute_configuration unk
_chemical_oxdiff_formula         'C7 H1 F4 I1 O2'
_chemical_oxdiff_usercomment     'Akihiro AT44 L'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
I -0.41187 1.83264 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z

_cell_length_a                   6.7596(2)
_cell_length_b                   31.6474(8)
_cell_length_c                   7.9922(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.548(3)
_cell_angle_gamma                90
_cell_volume                     1620.92(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10149
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      30.0135
_cell_measurement_theta_min      2.9747
_exptl_absorpt_coefficient_mu    3.989
_exptl_absorpt_correction_T_max  0.434
_exptl_absorpt_correction_T_min  0.140
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_density_diffrn    2.6222
_exptl_crystal_F_000             1181.6836
_exptl_crystal_size_max          0.266
_exptl_crystal_size_mid          0.1624
_exptl_crystal_size_min          0.0939
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            15874
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.08
_diffrn_reflns_theta_min         2.98
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.922536
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -90.00   -3.00   0.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.3259  109.0000   51.0000 174

#__ type_ start__ end____ width___ exp.time_
  2 omega  -56.00  -14.00   0.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.3259  109.0000 -134.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega  -64.00  -39.00   0.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.3259  109.0000 -128.0000 50

#__ type_ start__ end____ width___ exp.time_
  4 omega  -88.00  -61.00   0.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.3259  109.0000 -134.0000 54

#__ type_ start__ end____ width___ exp.time_
  5 omega   16.00   41.00   0.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       33.5759 -109.0000  128.0000 50

#__ type_ start__ end____ width___ exp.time_
  6 omega   16.00   41.00   0.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       33.5759 -109.0000  134.0000 50

#__ type_ start__ end____ width___ exp.time_
  7 omega  -23.00    4.00   0.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.6250  109.0000 -128.0000 54

#__ type_ start__ end____ width___ exp.time_
  8 omega  -64.00   46.00   0.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.3259   37.0000  -90.0000 220

#__ type_ start__ end____ width___ exp.time_
  9 omega -105.00   -4.00   0.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.3259  -57.0000  120.0000 202

#__ type_ start__ end____ width___ exp.time_
 10 omega   -6.00   32.00   0.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       33.5759  -57.0000    0.0000 76

#__ type_ start__ end____ width___ exp.time_
 11 omega  -18.00    7.00   0.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.4821  -77.0000 -180.0000 50

#__ type_ start__ end____ width___ exp.time_
 12 omega -103.00  -77.00   0.5000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.4821  -77.0000 -180.0000 52
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0174970000
_diffrn_orient_matrix_UB_12      0.0217969000
_diffrn_orient_matrix_UB_13      -0.0101379000
_diffrn_orient_matrix_UB_21      0.0959032000
_diffrn_orient_matrix_UB_22      -0.0012202000
_diffrn_orient_matrix_UB_23      0.0698912000
_diffrn_orient_matrix_UB_31      0.0522487000
_diffrn_orient_matrix_UB_32      -0.0050475000
_diffrn_orient_matrix_UB_33      -0.0616208000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.851
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              44
_reflns_limit_k_min              -44
_reflns_limit_l_max              11
_reflns_limit_l_min              -11
_reflns_number_gt                8382
_reflns_number_total             8789
_reflns_odcompleteness_completeness 99.10
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.977794
_refine_diff_density_min         -1.499360
_refine_diff_density_rms         0.162151
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.43(2)
_refine_ls_d_res_high            0.709010
_refine_ls_d_res_low             6.833966
_refine_ls_goodness_of_fit_ref   1.046121
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_constraints    4
_refine_ls_number_parameters     517
_refine_ls_number_reflns         8789
_refine_ls_number_restraints     144
_refine_ls_R_factor_all          0.035918
_refine_ls_R_factor_gt           0.034122
_refine_ls_restrained_S_all      1.037133
_refine_ls_shift/su_max          0.0017
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0286P)²+6.5845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.084841
_refine_special_details          
;
 The asymmetric unit conatained for molecules which
 only differed in the orientation of the carboylate
 groups. The phenyl carbons often showed poor ADP
 due to correlations between equivalent atoms in
 each of the rings. The ADP of these phenyl carbons
 were restrained to be approximately isotropic.

 The crystal also exhibited racemic twinning which 
 was accounted for using a inversion twin matrix. 
 The proportion of the two forms refined to 57:43
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
C1 C 0.1677(8) 0.61305(18) 0.2387(7) 0.0123(10) Uani 1.000000 .
C2 C 0.2105(8) 0.64980(18) 0.1362(7) 0.0123(9) Uani 1.000000 .
C3 C 0.2103(8) 0.64785(17) -0.0357(6) 0.0113(9) Uani 1.000000 .
C4 C 0.2433(8) 0.68305(19) -0.1245(7) 0.0159(10) Uani 1.000000 .
C5 C 0.2817(8) 0.72157(19) -0.0484(7) 0.0139(10) Uani 1.000000 .
C6 C 0.2859(9) 0.7242(2) 0.1260(8) 0.0183(11) Uani 1.000000 .
C7 C 0.2494(9) 0.68984(19) 0.2185(7) 0.0143(10) Uani 1.000000 .
F1 F 0.1700(5) 0.61094(11) -0.1234(4) 0.0176(7) Uani 1.000000 .
F2 F 0.2427(6) 0.67783(12) -0.2913(4) 0.0198(7) Uani 1.000000 .
F3 F 0.3223(6) 0.76245(11) 0.2126(5) 0.0230(8) Uani 1.000000 .
F4 F 0.2589(6) 0.69542(13) 0.3882(4) 0.0246(8) Uani 1.000000 .
I1 I 0.33459(5) 0.775028(8) -0.18078(4) 0.01908(9) Uani 1.000000 .
O1 O 0.2620(6) 0.61092(13) 0.4057(5) 0.0212(8) Uani 1.000000 .
O2 O 0.0456(6) 0.58589(13) 0.1485(5) 0.0206(8) Uani 1.000000 .
H2 H 0.028(11) 0.566(3) 0.212(10) 0.0309(12) Uiso 1.000000 .
C8 C 0.6658(8) 0.61306(17) 0.7372(7) 0.0113(9) Uani 1.000000 .
C9 C 0.7157(8) 0.64910(19) 0.6351(7) 0.0140(10) Uani 1.000000 .
C10 C 0.7417(8) 0.64596(17) 0.4696(7) 0.0138(10) Uani 1.000000 .
C11 C 0.7750(10) 0.6806(2) 0.3803(8) 0.0198(12) Uani 1.000000 .
C12 C 0.7902(8) 0.72056(18) 0.4465(7) 0.0142(10) Uani 1.000000 .
C13 C 0.7710(8) 0.72418(18) 0.6147(7) 0.0138(10) Uani 1.000000 .
C14 C 0.7324(7) 0.69031(17) 0.7084(6) 0.0105(9) Uani 1.000000 .
F5 F 0.7287(6) 0.60802(11) 0.3906(5) 0.0237(8) Uani 1.000000 .
F6 F 0.7960(6) 0.67401(12) 0.2203(4) 0.0243(8) Uani 1.000000 .
F7 F 0.7906(6) 0.76307(11) 0.6928(5) 0.0194(7) Uani 1.000000 .
F8 F 0.7247(5) 0.69756(12) 0.8713(4) 0.0190(7) Uani 1.000000 .
I2 I 0.85096(5) 0.772982(8) 0.31344(4) 0.01987(10) Uani 1.000000 .
O3 O 0.7186(7) 0.57652(13) 0.6895(5) 0.0210(8) Uani 1.000000 .
H3 H 0.685(12) 0.559(2) 0.744(10) 0.0316(12) Uiso 1.000000 .
O4 O 0.6060(7) 0.61858(13) 0.8644(5) 0.0237(8) Uani 1.000000 .
C15 C 1.0649(9) 0.51990(19) 0.5006(7) 0.0158(11) Uani 1.000000 .
C16 C 1.0303(8) 0.48240(18) 0.6017(7) 0.0126(9) Uani 1.000000 .
C17 C 1.0389(9) 0.48522(18) 0.7786(7) 0.0161(10) Uani 1.000000 .
C18 C 0.9965(8) 0.45057(18) 0.8690(7) 0.0143(10) Uani 1.000000 .
C19 C 0.9595(8) 0.41094(17) 0.7861(7) 0.0116(9) Uani 1.000000 .
C20 C 0.9587(7) 0.40774(17) 0.6150(6) 0.0097(9) Uani 1.000000 .
C21 C 0.9841(8) 0.44322(18) 0.5236(6) 0.0122(9) Uani 1.000000 .
F9 F 1.0810(6) 0.52151(11) 0.8694(5) 0.0209(7) Uani 1.000000 .
F10 F 1.0068(6) 0.45466(12) 1.0367(4) 0.0195(7) Uani 1.000000 .
F11 F 0.9258(5) 0.37122(11) 0.5322(4) 0.0165(7) Uani 1.000000 .
F12 F 0.9853(5) 0.43803(10) 0.3596(4) 0.0146(6) Uani 1.000000 .
I3 I 0.90704(5) 0.358917(8) 0.92286(4) 0.01847(9) Uani 1.000000 .
O5 O 1.2042(7) 0.54768(13) 0.6041(5) 0.0216(8) Uani 1.000000 .
H5 H 1.224(12) 0.566(3) 0.558(11) 0.0323(12) Uiso 1.000000 .
O6 O 0.9912(6) 0.52291(13) 0.3482(5) 0.0210(8) Uani 1.000000 .
C22 C 0.5670(9) 0.52087(19) 0.0042(8) 0.0178(11) Uani 1.000000 .
C23 C 0.5256(8) 0.48407(18) 0.1041(7) 0.0133(10) Uani 1.000000 .
C24 C 0.5045(9) 0.48825(18) 0.2725(7) 0.0165(10) Uani 1.000000 .
C25 C 0.4700(8) 0.45380(17) 0.3673(7) 0.0120(9) Uani 1.000000 .
C26 C 0.4505(8) 0.41279(19) 0.2914(7) 0.0149(10) Uani 1.000000 .
C27 C 0.4707(9) 0.40847(19) 0.1267(7) 0.0151(10) Uani 1.000000 .
C28 C 0.5013(9) 0.4436(2) 0.0353(7) 0.0189(11) Uani 1.000000 .
F13 F 0.5224(6) 0.52510(12) 0.3551(5) 0.0237(8) Uani 1.000000 .
F14 F 0.4559(6) 0.45917(13) 0.5273(4) 0.0226(8) Uani 1.000000 .
F15 F 0.4539(6) 0.37125(12) 0.0504(5) 0.0235(8) Uani 1.000000 .
F16 F 0.5167(6) 0.43691(11) -0.1233(5) 0.0216(8) Uani 1.000000 .
I4 I 0.39351(5) 0.361394(8) 0.42885(4) 0.02005(10) Uani 1.000000 .
O7 O 0.5354(8) 0.55790(13) 0.0654(6) 0.0244(9) Uani 1.000000 .
H7 H 0.540(13) 0.573(3) 0.012(11) 0.0366(13) Uiso 1.000000 .
O8 O 0.6464(7) 0.51561(12) -0.1110(5) 0.0232(8) Uani 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.502(7) .
C1 O1 1.285(6) .
C1 O2 1.250(7) .
C2 C3 1.375(7) .
C2 C7 1.413(8) .
C3 C4 1.377(8) .
C3 F1 1.345(6) .
C4 C5 1.350(8) .
C4 F2 1.342(6) .
C5 C6 1.387(8) .
C5 I1 2.086(6) .
C6 C7 1.380(8) .
C6 F3 1.378(7) .
C7 F4 1.349(6) .
O2 H2 0.85(8) .
C8 C9 1.502(8) .
C8 O3 1.302(7) .
C8 O4 1.221(6) .
C9 C10 1.393(7) .
C9 C14 1.420(8) .
C10 C11 1.365(8) .
C10 F5 1.346(6) .
C11 C12 1.362(8) .
C11 F6 1.347(7) .
C12 C13 1.395(7) .
C12 I2 2.081(6) .
C13 C14 1.380(8) .
C13 F7 1.367(7) .
C14 F8 1.339(6) .
O3 H3 0.78(7) .
C15 C16 1.495(8) .
C15 O5 1.360(7) .
C15 O6 1.164(7) .
C16 C17 1.400(7) .
C16 C21 1.379(8) .
C17 C18 1.392(8) .
C17 F9 1.340(7) .
C18 C19 1.403(8) .
C18 F10 1.327(6) .
C19 C20 1.369(7) .
C19 I3 2.068(5) .
C20 C21 1.380(8) .
C20 F11 1.315(6) .
C21 F12 1.324(6) .
O5 H5 0.71(8) .
C22 C23 1.488(8) .
C22 O7 1.313(8) .
C22 O8 1.216(7) .
C23 C24 1.404(7) .
C23 C28 1.382(8) .
C24 C25 1.389(8) .
C24 F13 1.326(7) .
C25 C26 1.421(8) .
C25 F14 1.324(6) .
C26 C27 1.373(8) .
C26 I4 2.066(6) .
C27 C28 1.383(9) .
C27 F15 1.315(7) .
C28 F16 1.321(7) .
O7 H7 0.64(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
O1 C1 C2 119.3(5) . .
O2 C1 C2 115.1(5) . .
O2 C1 O1 125.6(5) . .
C3 C2 C1 124.8(5) . .
C7 C2 C1 118.7(5) . .
C7 C2 C3 116.5(5) . .
C4 C3 C2 122.0(5) . .
F1 C3 C2 119.7(5) . .
F1 C3 C4 118.2(5) . .
C5 C4 C3 122.5(5) . .
F2 C4 C3 117.6(5) . .
F2 C4 C5 119.9(5) . .
C6 C5 C4 116.5(5) . .
I1 C5 C4 122.9(4) . .
I1 C5 C6 120.6(4) . .
C7 C6 C5 122.8(6) . .
F3 C6 C5 120.0(5) . .
F3 C6 C7 117.2(5) . .
C6 C7 C2 119.7(5) . .
F4 C7 C2 121.8(5) . .
F4 C7 C6 118.4(5) . .
H2 O2 C1 112(5) . .
O3 C8 C9 112.7(4) . .
O4 C8 C9 122.4(5) . .
O4 C8 O3 124.4(5) . .
C10 C9 C8 125.5(5) . .
C14 C9 C8 118.4(4) . .
C14 C9 C10 116.1(5) . .
C11 C10 C9 122.1(5) . .
F5 C10 C9 120.0(5) . .
F5 C10 C11 117.9(5) . .
C12 C11 C10 123.2(5) . .
F6 C11 C10 117.2(5) . .
F6 C11 C12 119.7(5) . .
C13 C12 C11 115.6(5) . .
I2 C12 C11 123.0(4) . .
I2 C12 C13 121.4(4) . .
C14 C13 C12 123.4(5) . .
F7 C13 C12 119.3(5) . .
F7 C13 C14 117.3(5) . .
C13 C14 C9 119.6(5) . .
F8 C14 C9 122.4(5) . .
F8 C14 C13 117.9(5) . .
H3 O3 C8 108(6) . .
O5 C15 C16 112.4(5) . .
O6 C15 C16 122.8(5) . .
O6 C15 O5 124.5(5) . .
C17 C16 C15 122.1(5) . .
C21 C16 C15 121.4(5) . .
C21 C16 C17 116.4(5) . .
C18 C17 C16 121.7(5) . .
F9 C17 C16 122.3(5) . .
F9 C17 C18 116.0(5) . .
C19 C18 C17 119.6(5) . .
F10 C18 C17 119.6(5) . .
F10 C18 C19 120.6(5) . .
C20 C19 C18 118.7(5) . .
I3 C19 C18 119.8(4) . .
I3 C19 C20 121.5(4) . .
C21 C20 C19 120.5(5) . .
F11 C20 C19 120.9(5) . .
F11 C20 C21 118.6(5) . .
C20 C21 C16 122.7(5) . .
F12 C21 C16 119.2(5) . .
F12 C21 C20 117.7(5) . .
H5 O5 C15 114(7) . .
O7 C22 C23 114.7(5) . .
O8 C22 C23 120.2(5) . .
O8 C22 O7 124.6(5) . .
C24 C23 C22 122.3(5) . .
C28 C23 C22 122.0(5) . .
C28 C23 C24 115.7(5) . .
C25 C24 C23 122.3(5) . .
F13 C24 C23 122.6(5) . .
F13 C24 C25 115.1(5) . .
C26 C25 C24 119.6(5) . .
F14 C25 C24 120.2(5) . .
F14 C25 C26 120.3(5) . .
C27 C26 C25 118.4(5) . .
I4 C26 C25 120.0(4) . .
I4 C26 C27 121.6(4) . .
C28 C27 C26 120.3(6) . .
F15 C27 C26 120.9(5) . .
F15 C27 C28 118.8(5) . .
C27 C28 C23 123.6(5) . .
F16 C28 C23 119.7(5) . .
F16 C28 C27 116.6(6) . .
H7 O7 C22 111(8) . .

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O6 0.85(8) 1.80(8) 2.651(5) 179(8) 1_455
O3 H3 O8 0.78(7) 1.87(8) 2.644(5) 172(8) 1_556
O5 H5 O1 0.71(8) 1.95(8) 2.659(5) 173(9) 1_655
O7 H7 O4 0.64(8) 2.00(8) 2.642(5) 171(10) 1_554

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 -1 0 0.0469 0.0000 -0.9985 0.0002 -0.0218 0.0012 0.0050
0 1 0 0.0469 -0.0000 0.9985 -0.0002 0.0218 -0.0012 -0.0050
-1 1 1 0.0712 -0.9985 0.9975 0.9989 -0.0059 -0.0272 -0.1188
1 -1 -1 0.0712 0.9985 -0.9975 -0.9989 0.0059 0.0272 0.1188
1 0 0 0.0977 0.9988 0.0029 -0.0012 0.0176 0.0957 0.0522
-1 -1 -1 0.0916 -0.9991 -1.0033 -0.9966 -0.0292 -0.1642 0.0143
0 1 1 0.1275 0.0003 1.0004 0.9977 0.0117 0.0685 -0.0665

loop_
_restr_U_iso_atom_site_label
_restr_U_iso_weight_param
C2 0.0020
C3 0.0020
C4 0.0020
C5 0.0020
C6 0.0020
C7 0.0020
C9 0.0020
C10 0.0020
C11 0.0020
C12 0.0020
C13 0.0020
C14 0.0020
C16 0.0020
C17 0.0020
C18 0.0020
C19 0.0020
C20 0.0020
C21 0.0020
C23 0.0020
C24 0.0020
C25 0.0020
C26 0.0020
C27 0.0020
C28 0.0020
_database_code_depnum_ccdc_archive 'CCDC 985842'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_dwb1218_twin1_hklf4
_audit_creation_date             2012-03-13
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C7 H F4 I O2, 0.5(C4 H8 S2)'
_chemical_formula_sum            'C9 H5 F4 I O2 S'
_chemical_formula_weight         380.09
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C9 H5 F4 I1 O2 S'
_chemical_oxdiff_usercomment     'Akihiro AT33 - F'
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'
I I -0.4742 1.8119 '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'
S S 0.1246 0.1234 '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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   6.2546(4)
_cell_length_b                   7.8761(4)
_cell_length_c                   11.5781(6)
_cell_angle_alpha                78.743(5)
_cell_angle_beta                 75.347(5)
_cell_angle_gamma                83.455(5)
_cell_volume                     539.94(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8780
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      30.0138
_cell_measurement_theta_min      2.9362
_exptl_absorpt_coefficient_mu    3.200
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    2.338
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.2195
_exptl_crystal_size_mid          0.1711
_exptl_crystal_size_min          0.1089
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6552
_diffrn_reflns_theta_full        30.18
_diffrn_reflns_theta_max         30.18
_diffrn_reflns_theta_min         2.95
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -94.00    3.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.1672  -77.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
  2 omega  -72.00  -35.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.1672 -178.0000 -120.0000 37

#__ type_ start__ end____ width___ exp.time_
  3 omega  -42.00   29.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172  -57.0000   30.0000 71

#__ type_ start__ end____ width___ exp.time_
  4 omega   -2.00   43.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172   82.0000    1.0000 45

#__ type_ start__ end____ width___ exp.time_
  5 omega  -40.00   54.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172  -77.0000  -90.0000 94

#__ type_ start__ end____ width___ exp.time_
  6 omega    2.00   97.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172   77.0000  120.0000 95

#__ type_ start__ end____ width___ exp.time_
  7 omega -101.00  -35.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.1672 -178.0000   60.0000 66

#__ type_ start__ end____ width___ exp.time_
  8 omega  -94.00   -4.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.1672  -57.0000  -90.0000 90

#__ type_ start__ end____ width___ exp.time_
  9 omega    5.00   95.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172   57.0000   60.0000 90

#__ type_ start__ end____ width___ exp.time_
 10 omega   35.00  102.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172  178.0000  -30.0000 67

#__ type_ start__ end____ width___ exp.time_
 11 omega  -20.00   68.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172  -99.0000   60.0000 88

#__ type_ start__ end____ width___ exp.time_
 12 omega  -94.00   -4.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.1672  -57.0000 -150.0000 90

#__ type_ start__ end____ width___ exp.time_
 13 omega  -39.00    7.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.1672  -83.0000   60.0000 46

#__ type_ start__ end____ width___ exp.time_
 14 omega  -46.00   52.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172  -37.0000  -90.0000 98

#__ type_ start__ end____ width___ exp.time_
 15 omega    1.00   99.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172   37.0000   30.0000 98

#__ type_ start__ end____ width___ exp.time_
 16 omega  -20.00   68.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4172  -99.0000  150.0000 88
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0888221000
_diffrn_orient_matrix_UB_12      -0.0520394000
_diffrn_orient_matrix_UB_13      -0.0296917000
_diffrn_orient_matrix_UB_21      0.0282898000
_diffrn_orient_matrix_UB_22      0.0709506000
_diffrn_orient_matrix_UB_23      -0.0477690000
_diffrn_orient_matrix_UB_31      0.0711561000
_diffrn_orient_matrix_UB_32      0.0265333000
_diffrn_orient_matrix_UB_33      0.0309835000
loop_
_diffrn_oxdiff_twin_id
_diffrn_oxdiff_twin_ratio
_diffrn_oxdiff_twin_reflns_isolated
_diffrn_oxdiff_twin_reflns_overlapped
1 0.6102 14887 1103
2 0.3898 15124 1103

_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                6028
_reflns_number_total             6552
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         1.066
_refine_diff_density_min         -0.679
_refine_diff_density_rms         0.151
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         6552
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0673P)²+0.6281P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1025
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

 Non-merohedral twin modelled with Chrysalis and HKLF5.  2 components with
 refined ratio of  0.6102:0.3898

;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2515(4) 0.3573(3) 0.4378(2) 0.0139(4) Uani 1 1 d . . .
C2 C 0.4501(4) 0.2481(3) 0.3873(2) 0.0127(4) Uani 1 1 d . . .
C3 C 0.6599(4) 0.3113(3) 0.3453(2) 0.0133(4) Uani 1 1 d . . .
C4 C 0.8381(4) 0.2127(3) 0.2897(2) 0.0133(4) Uani 1 1 d . . .
C5 C 0.8161(4) 0.0479(3) 0.2701(2) 0.0138(4) Uani 1 1 d . . .
C6 C 0.6095(4) -0.0170(3) 0.3144(2) 0.0137(4) Uani 1 1 d . . .
C7 C 0.4308(4) 0.0793(3) 0.3736(2) 0.0129(4) Uani 1 1 d . . .
F1 F 0.6958(3) 0.46944(19) 0.35832(16) 0.0188(3) Uani 1 1 d . . .
F2 F 1.0353(3) 0.2822(2) 0.25025(15) 0.0179(3) Uani 1 1 d . . .
F3 F 0.5765(3) -0.17521(19) 0.29983(16) 0.0193(3) Uani 1 1 d . . .
F4 F 0.2363(2) 0.0083(2) 0.41355(15) 0.0166(3) Uani 1 1 d . . .
I1 I 1.07821(2) -0.083553(19) 0.166297(14) 0.01592(6) Uani 1 1 d . . .
O1 O 0.2570(3) 0.5200(2) 0.38442(18) 0.0193(4) Uani 1 1 d . . .
H1 H 0.125(8) 0.573(6) 0.417(4) 0.039(12) Uiso 1 1 d . . .
O2 O 0.1004(3) 0.2952(2) 0.51888(18) 0.0178(4) Uani 1 1 d . . .
C8 C 1.6329(5) -0.3951(4) 0.0581(3) 0.0195(5) Uani 1 1 d . . .
H8A H 1.7463 -0.3201 0.0572 0.023 Uiso 1 1 calc R . .
H8B H 1.5518 -0.4273 0.1416 0.023 Uiso 1 1 calc R . .
C9 C 1.2578(4) -0.4432(3) -0.0103(2) 0.0174(5) Uani 1 1 d . . .
H9A H 1.1890 -0.4746 0.0753 0.021 Uiso 1 1 calc R . .
H9B H 1.1414 -0.3962 -0.0516 0.021 Uiso 1 1 calc R . .
S1 S 1.44568(11) -0.27708(8) -0.02944(6) 0.01841(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 C2 1.487(3) . ?
C1 O1 1.309(3) . ?
C1 O2 1.221(3) . ?
C2 C3 1.392(3) . ?
C2 C7 1.391(3) . ?
C3 C4 1.376(3) . ?
C3 F1 1.333(3) . ?
C4 C5 1.388(3) . ?
C4 F2 1.342(3) . ?
C5 C6 1.381(3) . ?
C5 I1 2.075(2) . ?
C6 C7 1.384(3) . ?
C6 F3 1.335(3) . ?
C7 F4 1.333(3) . ?
O1 H1 0.91(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.511(4) 2_845 ?
C8 S1 1.802(3) . ?
C9 C8 1.511(4) 2_845 ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 S1 1.802(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
O1 C1 C2 113.0(2) . . ?
O2 C1 C2 121.4(2) . . ?
O2 C1 O1 125.6(2) . . ?
C3 C2 C1 122.3(2) . . ?
C7 C2 C1 120.7(2) . . ?
C7 C2 C3 116.9(2) . . ?
C4 C3 C2 121.3(2) . . ?
F1 C3 C2 121.1(2) . . ?
F1 C3 C4 117.6(2) . . ?
C3 C4 C5 121.7(2) . . ?
F2 C4 C3 118.3(2) . . ?
F2 C4 C5 120.0(2) . . ?
C4 C5 I1 120.55(18) . . ?
C6 C5 C4 117.1(2) . . ?
C6 C5 I1 122.19(17) . . ?
C5 C6 C7 121.5(2) . . ?
F3 C6 C5 120.4(2) . . ?
F3 C6 C7 118.0(2) . . ?
C6 C7 C2 121.3(2) . . ?
F4 C7 C2 120.5(2) . . ?
F4 C7 C6 118.2(2) . . ?
C1 O1 H1 106(3) . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 H8A 109.1 2_845 . ?
C9 C8 H8B 109.1 2_845 . ?
C9 C8 S1 112.48(19) 2_845 . ?
S1 C8 H8A 109.1 . . ?
S1 C8 H8B 109.1 . . ?
C8 C9 H9A 108.8 2_845 . ?
C8 C9 H9B 108.8 2_845 . ?
C8 C9 S1 113.78(18) 2_845 . ?
H9A C9 H9B 107.7 . . ?
S1 C9 H9A 108.8 . . ?
S1 C9 H9B 108.8 . . ?
C8 S1 C9 99.23(12) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.91(5) 1.75(5) 2.645(3) 170(5) 2_566

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
C1 C2 C3 C4 -174.6(2) . . . . ?
C1 C2 C3 F1 5.9(4) . . . . ?
C1 C2 C7 C6 172.6(2) . . . . ?
C1 C2 C7 F4 -4.7(4) . . . . ?
C2 C3 C4 C5 1.7(4) . . . . ?
C2 C3 C4 F2 179.3(2) . . . . ?
C3 C2 C7 C6 -3.9(4) . . . . ?
C3 C2 C7 F4 178.8(2) . . . . ?
C3 C4 C5 C6 -3.3(4) . . . . ?
C3 C4 C5 I1 171.88(19) . . . . ?
C4 C5 C6 C7 1.3(4) . . . . ?
C4 C5 C6 F3 -179.4(2) . . . . ?
C5 C6 C7 C2 2.3(4) . . . . ?
C5 C6 C7 F4 179.8(2) . . . . ?
C7 C2 C3 C4 1.9(4) . . . . ?
C7 C2 C3 F1 -177.6(2) . . . . ?
F1 C3 C4 C5 -178.8(2) . . . . ?
F1 C3 C4 F2 -1.2(3) . . . . ?
F2 C4 C5 C6 179.2(2) . . . . ?
F2 C4 C5 I1 -5.7(3) . . . . ?
F3 C6 C7 C2 -177.0(2) . . . . ?
F3 C6 C7 F4 0.4(3) . . . . ?
I1 C5 C6 C7 -173.80(19) . . . . ?
I1 C5 C6 F3 5.5(3) . . . . ?
O1 C1 C2 C3 34.6(3) . . . . ?
O1 C1 C2 C7 -141.7(2) . . . . ?
O2 C1 C2 C3 -146.9(3) . . . . ?
O2 C1 C2 C7 36.8(4) . . . . ?
C8 C9 S1 C8 -60.3(2) 2_845 . . . ?
C9 C8 S1 C9 59.4(2) 2_845 . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1 -1 0 0.0988 -1.0020 -1.0005 -0.0007 -0.0369 -0.0993 -0.0979
-1 -1 -4 0.0737 -1.0017 -1.0001 -4.0054 0.0820 0.0920 -0.2219
1 2 -1 0.0946 1.0022 2.0022 -1.0001 0.0145 0.2182 0.0935
-1 1 0 0.0604 -1.0016 1.0025 0.0001 -0.1411 0.0428 -0.0447
1 -1 0 0.0484 1.0016 -1.0025 -0.0001 0.1411 -0.0428 0.0447
0 1 1 0.0827 0.0001 1.0014 1.0016 -0.0818 0.0232 0.0576
-1 1 4 0.0710 -1.0019 1.0021 4.0048 -0.2600 -0.1485 0.0794
-1 0 -3 0.0695 -1.0016 0.0013 -3.0039 0.0002 0.1153 -0.1643
-1 -3 0 0.0959 -1.0023 -3.0036 -0.0015 0.0673 -0.2414 -0.1511
1 0 5 0.0640 1.0014 -0.0015 5.0062 -0.0596 -0.2109 0.2263
_database_code_depnum_ccdc_archive 'CCDC 985843'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_dwb1234
_audit_creation_date             2012-05-18
_audit_creation_method           
;
  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C7 F4 I O2), 2(C4 H10 N S), C4 H9 N S'
_chemical_formula_sum            'C26 H29 F8 I2 N3 O4 S3'
_chemical_formula_weight         949.50
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 F4 I1 N1 O2 S1'
_chemical_oxdiff_usercomment     'Akihiro AT48 C2A'
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'
I I -0.4742 1.8119 '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'
S S 0.1246 0.1234 '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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   5.7209(7)
_cell_length_b                   10.3273(13)
_cell_length_c                   14.4539(17)
_cell_angle_alpha                107.044(11)
_cell_angle_beta                 99.741(10)
_cell_angle_gamma                92.149(10)
_cell_volume                     801.23(17)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2087
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      29.7735
_cell_measurement_theta_min      2.9997
_exptl_absorpt_coefficient_mu    2.243
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.876
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.968
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.1982
_exptl_crystal_size_mid          0.0576
_exptl_crystal_size_min          0.0177
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6397
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         29.86
_diffrn_reflns_theta_min         3.00
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.877
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -91.00   -2.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4517  -77.0000   90.0000 89

#__ type_ start__ end____ width___ exp.time_
  2 omega    6.00   46.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4517   77.0000 -150.0000 40

#__ type_ start__ end____ width___ exp.time_
  3 omega  -50.00   46.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4517   77.0000  -60.0000 96

#__ type_ start__ end____ width___ exp.time_
  4 omega  -43.00   -9.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4517  -78.0000   16.0000 34

#__ type_ start__ end____ width___ exp.time_
  5 omega  -89.00   10.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4517  -77.0000 -180.0000 99

#__ type_ start__ end____ width___ exp.time_
  6 omega    1.00   35.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       21.5455  -57.0000  -30.0000 34
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1016886000
_diffrn_orient_matrix_UB_12      0.0463827000
_diffrn_orient_matrix_UB_13      0.0089145000
_diffrn_orient_matrix_UB_21      -0.0349165000
_diffrn_orient_matrix_UB_22      0.0407230000
_diffrn_orient_matrix_UB_23      0.0433870000
_diffrn_orient_matrix_UB_31      0.0664295000
_diffrn_orient_matrix_UB_32      -0.0371042000
_diffrn_orient_matrix_UB_33      0.0278676000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3224
_reflns_number_total             4026
_reflns_odcompleteness_completeness 99.01
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_reflns_threshold_expression     >2sigma(I)
_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_collection       
;
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_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         3.307
_refine_diff_density_min         -1.378
_refine_diff_density_rms         0.164
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         4026
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0383P)²+2.2099P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1123
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

 All hydrogens including N-H were placed using a riding model.
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9626(8) 0.3660(5) 0.3412(3) 0.0182(10) Uani 1 1 d . . .
C2 C 0.7480(8) 0.3026(5) 0.2828(4) 0.0188(10) Uani 1 1 d . . .
C3 C 0.5864(8) 0.3728(5) 0.2392(4) 0.0190(10) Uani 1 1 d . . .
C4 C 0.6291(8) 0.5105(5) 0.2505(3) 0.0158(9) Uani 1 1 d . . .
C5 C 0.8453(8) 0.5731(5) 0.3098(4) 0.0189(10) Uani 1 1 d . . .
C6 C 1.0050(8) 0.5033(5) 0.3552(4) 0.0195(10) Uani 1 1 d . . .
C7 C 0.4580(8) 0.5889(5) 0.1978(3) 0.0182(10) Uani 1 1 d . . .
F1 F 0.6977(5) 0.1679(3) 0.2643(2) 0.0268(7) Uani 1 1 d . . .
F2 F 0.3815(5) 0.3033(3) 0.1831(2) 0.0259(7) Uani 1 1 d . . .
F3 F 0.9019(5) 0.7063(3) 0.3256(2) 0.0276(7) Uani 1 1 d . . .
F4 F 1.2082(5) 0.5717(3) 0.4121(2) 0.0304(8) Uani 1 1 d . . .
I1 I 1.21828(6) 0.26091(4) 0.40445(3) 0.02697(12) Uani 1 1 d . . .
O1 O 0.2428(6) 0.5662(4) 0.1966(3) 0.0256(8) Uani 1 1 d . . .
O2 O 0.5470(6) 0.6678(4) 0.1606(3) 0.0341(10) Uani 1 1 d . . .
C8 C 0.1215(9) 0.6891(5) -0.0319(4) 0.0246(11) Uani 1 1 d . . .
H8A H 0.0791 0.6420 -0.1020 0.030 Uiso 1 1 calc R . .
H8B H 0.2478 0.6439 -0.0040 0.030 Uiso 1 1 calc R . .
C9 C -0.0924(8) 0.6797(5) 0.0150(4) 0.0206(10) Uani 1 1 d . . .
H9A H -0.2190 0.7248 -0.0129 0.025 Uiso 1 1 calc R . .
H9B H -0.1494 0.5848 0.0000 0.025 Uiso 1 1 calc R . .
C10 C 0.0309(10) 0.8930(5) 0.1532(4) 0.0264(11) Uani 1 1 d . . .
H10A H 0.0553 0.9297 0.2244 0.032 Uiso 1 1 calc R . .
H10B H -0.0991 0.9361 0.1255 0.032 Uiso 1 1 calc R . .
C11 C 0.2552(10) 0.9260(5) 0.1186(4) 0.0316(13) Uani 1 1 d . . .
H11A H 0.3866 0.8869 0.1494 0.038 Uiso 1 1 calc R . .
H11B H 0.2922 1.0239 0.1401 0.038 Uiso 1 1 calc R . .
N1 N -0.0356(7) 0.7428(4) 0.1234(3) 0.0201(9) Uani 1 1 d . . .
H1A H 0.0859 0.7030 0.1488 0.024 Uiso 1 1 calc R . .
H1B H -0.1628 0.7273 0.1491 0.024 Uiso 1 1 calc R . .
S1 S 0.2298(3) 0.86299(14) -0.01377(11) 0.0312(3) Uani 1 1 d . . .
C12 C 0.4169(12) 0.8785(7) 0.4128(4) 0.051(2) Uani 1 1 d D . .
H12A H 0.4392 0.7872 0.3743 0.061 Uiso 0.50 1 calc PR A 1
H12B H 0.2797 0.9070 0.3768 0.061 Uiso 0.50 1 calc PR A 1
H12C H 0.4542 0.7854 0.3870 0.061 Uiso 0.50 1 calc PR A 2
H12D H 0.2881 0.8934 0.3650 0.061 Uiso 0.50 1 calc PR A 2
C13 C 0.3726(12) 1.0316(6) 0.5837(4) 0.0418(16) Uani 1 1 d D . .
H13A H 0.2327 1.0706 0.5591 0.050 Uiso 0.50 1 calc PR B 1
H13B H 0.3651 1.0354 0.6510 0.050 Uiso 0.50 1 calc PR B 1
H13C H 0.2337 1.0806 0.5741 0.050 Uiso 0.50 1 calc PR B 2
H13D H 0.3852 1.0192 0.6483 0.050 Uiso 0.50 1 calc PR B 2
N2 N 0.320(4) 0.8897(17) 0.5074(7) 0.0355(9) Uani 0.50 1 d PDU C 2
H2 H 0.1614 0.8698 0.4910 0.043 Uiso 0.50 1 d PR C 2
S2 S 0.3493(11) 0.8701(4) 0.5186(2) 0.0355(9) Uani 0.50 1 d PDU C 1


_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 C2 1.383(6) . ?
C1 C6 1.378(7) . ?
C1 I1 2.098(4) . ?
C2 C3 1.378(6) . ?
C2 F1 1.346(5) . ?
C3 C4 1.390(7) . ?
C3 F2 1.349(5) . ?
C4 C5 1.392(6) . ?
C4 C7 1.537(6) . ?
C5 C6 1.381(6) . ?
C5 F3 1.345(5) . ?
C6 F4 1.342(5) . ?
C7 O1 1.241(6) . ?
C7 O2 1.237(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.509(7) . ?
C8 S1 1.806(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 N1 1.484(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.516(8) . ?
C10 N1 1.498(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 S1 1.809(6) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C12 H12D 0.9700 . ?
C12 C13 1.477(8) 2_676 ?
C12 N2 1.536(14) . ?
C12 S2 1.664(7) . ?
C13 C12 1.477(8) 2_676 ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C13 H13D 0.9700 . ?
C13 N2 1.536(14) . ?
C13 S2 1.645(7) . ?
N2 H2 0.9001 . ?
S2 H2 1.0810 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 I1 122.6(3) . . ?
C6 C1 C2 116.8(4) . . ?
C6 C1 I1 120.6(3) . . ?
C3 C2 C1 121.6(4) . . ?
F1 C2 C1 119.8(4) . . ?
F1 C2 C3 118.6(4) . . ?
C2 C3 C4 122.3(4) . . ?
F2 C3 C2 117.8(4) . . ?
F2 C3 C4 119.8(4) . . ?
C3 C4 C5 115.4(4) . . ?
C3 C4 C7 123.2(4) . . ?
C5 C4 C7 121.3(4) . . ?
C6 C5 C4 122.2(4) . . ?
F3 C5 C4 119.8(4) . . ?
F3 C5 C6 118.0(4) . . ?
C1 C6 C5 121.6(4) . . ?
F4 C6 C1 120.0(4) . . ?
F4 C6 C5 118.4(4) . . ?
O1 C7 C4 116.4(4) . . ?
O2 C7 C4 117.3(4) . . ?
O2 C7 O1 126.3(4) . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C9 C8 S1 112.4(4) . . ?
S1 C8 H8A 109.1 . . ?
S1 C8 H8B 109.1 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N1 C9 C8 111.9(4) . . ?
N1 C9 H9A 109.2 . . ?
N1 C9 H9B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
N1 C10 H10A 109.2 . . ?
N1 C10 H10B 109.2 . . ?
N1 C10 C11 111.8(4) . . ?
C10 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C10 C11 S1 113.2(4) . . ?
H11A C11 H11B 107.8 . . ?
S1 C11 H11A 108.9 . . ?
S1 C11 H11B 108.9 . . ?
C9 N1 C10 112.8(4) . . ?
C9 N1 H1A 109.0 . . ?
C9 N1 H1B 109.0 . . ?
C10 N1 H1A 109.0 . . ?
C10 N1 H1B 109.0 . . ?
H1A N1 H1B 107.8 . . ?
C8 S1 C11 98.3(3) . . ?
H12A C12 H12B 107.1 . . ?
H12A C12 H12C 11.5 . . ?
H12A C12 H12D 96.2 . . ?
H12B C12 H12C 117.3 . . ?
H12B C12 H12D 11.9 . . ?
H12C C12 H12D 106.9 . . ?
C13 C12 H12A 107.7 2_676 . ?
C13 C12 H12B 107.7 2_676 . ?
C13 C12 H12C 107.4 2_676 . ?
C13 C12 H12D 107.4 2_676 . ?
C13 C12 N2 119.6(10) 2_676 . ?
C13 C12 S2 118.5(5) 2_676 . ?
N2 C12 H12A 115.6 . . ?
N2 C12 H12B 97.7 . . ?
N2 C12 H12C 107.4 . . ?
N2 C12 H12D 107.4 . . ?
N2 C12 S2 10.8(7) . . ?
S2 C12 H12A 107.7 . . ?
S2 C12 H12B 107.7 . . ?
S2 C12 H12C 98.6 . . ?
S2 C12 H12D 116.7 . . ?
C12 C13 H13A 107.4 2_676 . ?
C12 C13 H13B 107.4 2_676 . ?
C12 C13 H13C 107.2 2_676 . ?
C12 C13 H13D 107.2 2_676 . ?
C12 C13 N2 120.5(10) 2_676 . ?
C12 C13 S2 119.7(5) 2_676 . ?
H13A C13 H13B 106.9 . . ?
H13A C13 H13C 12.4 . . ?
H13A C13 H13D 117.7 . . ?
H13B C13 H13C 95.6 . . ?
H13B C13 H13D 12.1 . . ?
H13C C13 H13D 106.8 . . ?
N2 C13 H13A 97.3 . . ?
N2 C13 H13B 115.8 . . ?
N2 C13 H13C 107.2 . . ?
N2 C13 H13D 107.2 . . ?
N2 C13 S2 11.1(7) . . ?
S2 C13 H13A 107.4 . . ?
S2 C13 H13B 107.4 . . ?
S2 C13 H13C 116.5 . . ?
S2 C13 H13D 97.9 . . ?
C12 N2 C13 113.8(15) . . ?
C12 N2 H2 108.2 . . ?
C13 N2 H2 108.3 . . ?
C12 S2 H2 91.5 . . ?
C13 S2 C12 102.0(4) . . ?
C13 S2 H2 92.6 . . ?

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
C1 C2 C3 C4 0.4(8) . . . . ?
C1 C2 C3 F2 179.8(4) . . . . ?
C2 C1 C6 C5 -2.6(8) . . . . ?
C2 C1 C6 F4 179.1(5) . . . . ?
C2 C3 C4 C5 -0.7(7) . . . . ?
C2 C3 C4 C7 176.3(5) . . . . ?
C3 C4 C5 C6 -0.8(7) . . . . ?
C3 C4 C5 F3 -179.6(4) . . . . ?
C3 C4 C7 O1 43.7(7) . . . . ?
C3 C4 C7 O2 -136.1(5) . . . . ?
C4 C5 C6 C1 2.5(8) . . . . ?
C4 C5 C6 F4 -179.2(5) . . . . ?
C5 C4 C7 O1 -139.4(5) . . . . ?
C5 C4 C7 O2 40.7(7) . . . . ?
C6 C1 C2 C3 1.2(8) . . . . ?
C6 C1 C2 F1 178.5(4) . . . . ?
C7 C4 C5 C6 -177.8(4) . . . . ?
C7 C4 C5 F3 3.3(7) . . . . ?
F1 C2 C3 C4 -176.9(4) . . . . ?
F1 C2 C3 F2 2.5(7) . . . . ?
F2 C3 C4 C5 180.0(4) . . . . ?
F2 C3 C4 C7 -3.0(7) . . . . ?
F3 C5 C6 C1 -178.6(5) . . . . ?
F3 C5 C6 F4 -0.4(7) . . . . ?
I1 C1 C2 C3 -177.7(4) . . . . ?
I1 C1 C2 F1 -0.3(7) . . . . ?
I1 C1 C6 C5 176.3(4) . . . . ?
I1 C1 C6 F4 -2.0(7) . . . . ?
C8 C9 N1 C10 64.6(5) . . . . ?
C9 C8 S1 C11 51.9(4) . . . . ?
C10 C11 S1 C8 -50.9(4) . . . . ?
C11 C10 N1 C9 -62.8(5) . . . . ?
N1 C10 C11 S1 59.3(5) . . . . ?
S1 C8 C9 N1 -62.2(5) . . . . ?
C12 C13 N2 C12 -27.6(17) 2_676 . . . ?
C12 C13 S2 C12 -46.9(8) 2_676 . . . ?
C13 C12 N2 C13 27.4(17) 2_676 . . . ?
C13 C12 S2 C13 46.2(8) 2_676 . . . ?
N2 C12 S2 C13 -53(5) . . . . ?
N2 C13 S2 C12 50(5) . . . . ?
S2 C12 N2 C13 114(6) . . . . ?
S2 C13 N2 C12 -117(6) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 1 0.0088 0.0000 0.0000 1.0000 0.0089 0.0434 0.0279
0 0 -1 0.0088 -0.0000 -0.0000 -1.0000 -0.0089 -0.0434 -0.0279
1 0 0 0.0946 1.0000 -0.0000 -0.0000 0.1017 -0.0349 0.0664
-1 0 0 0.0946 -1.0000 0.0000 0.0000 -0.1017 0.0349 -0.0664
0 -1 1 0.0228 -0.0000 -1.0000 1.0001 -0.0375 0.0027 0.0650
0 1 -1 0.0228 0.0000 1.0000 -1.0001 0.0375 -0.0027 -0.0650
_database_code_depnum_ccdc_archive 'CCDC 985844'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_dwb1217
_audit_creation_date             2012-03-13
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C4 H8 O2 S2'
_chemical_formula_sum            'C4 H8 O2 S2'
_chemical_formula_weight         152.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C4 H8 O2 S2'
_chemical_oxdiff_usercomment     'Akihiro AT33 - A'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.2950(3)
_cell_length_b                   6.3948(5)
_cell_length_c                   8.090(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.161(13)
_cell_angle_gamma                90.00
_cell_volume                     315.78(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1133
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      31.7911
_cell_measurement_theta_min      3.1772
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_T_max  0.913
_exptl_absorpt_correction_T_min  0.869
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             160
_exptl_crystal_size_max          0.294
_exptl_crystal_size_mid          0.2065
_exptl_crystal_size_min          0.1504
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            1632
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         31.88
_diffrn_reflns_theta_min         3.69
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -68.00   43.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -25.1672   19.0000   30.0000 111

#__ type_ start__ end____ width___ exp.time_
  2 omega  -89.00  -49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -25.1672 -178.0000   60.0000 40

#__ type_ start__ end____ width___ exp.time_
  3 omega   21.00   96.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       26.4172   77.0000 -150.0000 75
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0308685000
_diffrn_orient_matrix_UB_12      0.0511821000
_diffrn_orient_matrix_UB_13      0.0803187000
_diffrn_orient_matrix_UB_21      -0.0958459000
_diffrn_orient_matrix_UB_22      -0.0380141000
_diffrn_orient_matrix_UB_23      0.0208634000
_diffrn_orient_matrix_UB_31      0.0573845000
_diffrn_orient_matrix_UB_32      -0.0906189000
_diffrn_orient_matrix_UB_33      0.0364965000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                866
_reflns_number_total             973
_reflns_odcompleteness_completeness 97.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     37
_refine_ls_number_reflns         973
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0292
_refine_ls_restrained_S_all      1.139
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0386P)²+0.0335P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0759
_refine_ls_wR_factor_ref         0.0827
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0573(2) 0.2805(2) 0.06068(19) 0.0133(3) Uani 1 1 d . . .
H1A H -0.1648 0.2444 -0.0434 0.016 Uiso 1 1 calc R . .
H1B H -0.0489 0.1650 0.1398 0.016 Uiso 1 1 calc R . .
C2 C 0.1336(2) 0.5255(2) -0.13709(18) 0.0135(3) Uani 1 1 d . . .
H2A H 0.2597 0.5611 -0.1805 0.016 Uiso 1 1 calc R . .
H2B H 0.0179 0.4790 -0.2326 0.016 Uiso 1 1 calc R . .
O1 O 0.35422(16) 0.40714(17) 0.17084(14) 0.0170(2) Uani 1 1 d . . .
S1 S 0.20643(5) 0.31388(5) 0.01325(4) 0.01319(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 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.516(2) 3_565 ?
C1 S1 1.8059(15) . ?
C2 C1 1.516(2) 3_565 ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 S1 1.8023(15) . ?
O1 S1 1.5054(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A C1 H1B 107.8 . . ?
C2 C1 H1A 109.0 3_565 . ?
C2 C1 H1B 109.0 3_565 . ?
C2 C1 S1 112.92(9) 3_565 . ?
S1 C1 H1A 109.0 . . ?
S1 C1 H1B 109.0 . . ?
C1 C2 H2A 109.0 3_565 . ?
C1 C2 H2B 109.0 3_565 . ?
C1 C2 S1 113.14(10) 3_565 . ?
H2A C2 H2B 107.8 . . ?
S1 C2 H2A 109.0 . . ?
S1 C2 H2B 109.0 . . ?
C2 S1 C1 97.87(7) . . ?
O1 S1 C1 106.06(7) . . ?
O1 S1 C2 106.05(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
C1 C2 S1 C1 60.88(12) 3_565 . . . ?
C1 C2 S1 O1 -48.41(11) 3_565 . . . ?
C2 C1 S1 C2 -60.71(12) 3_565 . . . ?
C2 C1 S1 O1 48.58(11) 3_565 . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1 0 -1 0.0842 0.9999 -0.0000 -0.9999 -0.0494 -0.1167 0.0209
1 -2 1 0.1033 1.0001 -2.0000 0.9997 0.0088 0.0010 0.2751
-1 0 0 0.1362 -1.0000 -0.0000 -0.0000 -0.0309 0.0958 -0.0574
1 -1 2 0.1124 1.0001 -1.0000 1.9998 0.1403 -0.0161 0.2210
1 0 0 0.1362 1.0000 0.0000 0.0000 0.0309 -0.0958 0.0574
0 1 1 0.0752 -0.0000 1.0000 1.0000 0.1315 -0.0171 -0.0541
0 -1 -1 0.0752 0.0000 -1.0000 -1.0000 -0.1315 0.0171 0.0541
0 1 -1 0.0956 -0.0001 1.0000 -0.9998 -0.0291 -0.0589 -0.1271
0 -1 1 0.0796 0.0001 -1.0000 0.9998 0.0291 0.0589 0.1271
-1 0 1 0.0752 -0.9999 0.0000 0.9999 0.0494 0.1167 -0.0209
_database_code_depnum_ccdc_archive 'CCDC 985845'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_dwb1373
_audit_creation_date             2013-12-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C6 H Br F4 O), C4 H8 O2 S2 '
_chemical_formula_sum            'C16 H10 Br2 F8 O4 S2'
_chemical_formula_weight         642.18
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H10 Br2 F8 O4 S2'
_chemical_oxdiff_usercomment     'Linda E348D'
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'
Br Br -0.2901 2.4595 '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'
S S 0.1246 0.1234 '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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   5.89886(16)
_cell_length_b                   21.0112(5)
_cell_length_c                   16.1143(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.557(3)
_cell_angle_gamma                90.00
_cell_volume                     1987.85(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4317
_cell_measurement_temperature    110.05(10)
_cell_measurement_theta_max      27.8210
_cell_measurement_theta_min      3.1540
_exptl_absorpt_coefficient_mu    4.386
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_correction_T_min  0.477
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.146
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plank
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.3096
_exptl_crystal_size_mid          0.0734
_exptl_crystal_size_min          0.0333
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11592
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         27.95
_diffrn_reflns_theta_min         3.17
_diffrn_ambient_temperature      110.05(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.9956
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0465490000
_diffrn_orient_matrix_UB_12      -0.0292104000
_diffrn_orient_matrix_UB_13      -0.0124119000
_diffrn_orient_matrix_UB_21      -0.0025336000
_diffrn_orient_matrix_UB_22      0.0114268000
_diffrn_orient_matrix_UB_23      -0.0415179000
_diffrn_orient_matrix_UB_31      0.1114328000
_diffrn_orient_matrix_UB_32      0.0124767000
_diffrn_orient_matrix_UB_33      0.0088822000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3503
_reflns_number_total             4103
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.01
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         4103
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0292
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0297P)²+0.6326P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0612
_refine_ls_wR_factor_ref         0.0651
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 

 The phenol hydrogen atoms were found by difference map, all other hydrogens
 were calculated.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
C13 C 0.2916(4) 0.46453(12) 0.08360(17) 0.0176(6) Uani 1 1 d . . .
H13A H 0.3792 0.4830 0.0417 0.021 Uiso 1 1 calc . . R
H13B H 0.1323 0.4741 0.0679 0.021 Uiso 1 1 calc . . R
C14 C 0.3635(5) 0.49554(12) 0.16696(18) 0.0185(6) Uani 1 1 d . . .
H14A H 0.2875 0.4742 0.2099 0.022 Uiso 1 1 calc . . R
H14B H 0.3143 0.5396 0.1651 0.022 Uiso 1 1 calc . . R
C15 C 0.6968(4) 0.40750(12) 0.19965(17) 0.0159(6) Uani 1 1 d . . .
H15A H 0.8540 0.3970 0.2178 0.019 Uiso 1 1 calc . . R
H15B H 0.6028 0.3909 0.2408 0.019 Uiso 1 1 calc . . R
C16 C 0.6294(4) 0.37557(12) 0.11653(17) 0.0174(6) Uani 1 1 d . . .
H16A H 0.6749 0.3312 0.1204 0.021 Uiso 1 1 calc . . R
H16B H 0.7125 0.3954 0.0744 0.021 Uiso 1 1 calc . . R
O3 O 0.2097(3) 0.35723(9) 0.15678(12) 0.0215(4) Uani 1 1 d . . .
O4 O 0.7715(3) 0.51204(9) 0.11605(12) 0.0187(4) Uani 1 1 d . . .
S1 S 0.32907(11) 0.37951(3) 0.08331(5) 0.01747(16) Uani 1 1 d . . .
S2 S 0.66643(11) 0.49285(3) 0.19467(4) 0.01662(15) Uani 1 1 d . . .
Br1 Br 0.27799(5) -0.009938(12) 0.077182(18) 0.01953(9) Uani 1 1 d . . .
C1 C 0.1914(4) 0.07193(12) 0.10677(16) 0.0147(6) Uani 1 1 d . . .
C2 C -0.0022(4) 0.08274(12) 0.14703(17) 0.0156(6) Uani 1 1 d . . .
C3 C -0.0656(4) 0.14287(12) 0.16867(17) 0.0154(6) Uani 1 1 d . . .
C4 C 0.0588(4) 0.19620(12) 0.14940(17) 0.0156(6) Uani 1 1 d . . .
C5 C 0.2523(4) 0.18483(12) 0.10935(18) 0.0155(6) Uani 1 1 d . . .
C6 C 0.3188(4) 0.12463(12) 0.08942(17) 0.0149(6) Uani 1 1 d . . .
F1 F -0.1322(3) 0.03317(7) 0.16664(10) 0.0214(4) Uani 1 1 d . . .
F2 F -0.2525(2) 0.15044(7) 0.20924(10) 0.0202(4) Uani 1 1 d . . .
F3 F 0.3809(3) 0.23504(7) 0.08929(11) 0.0233(4) Uani 1 1 d . . .
F4 F 0.5113(2) 0.11756(7) 0.05183(10) 0.0188(3) Uani 1 1 d . . .
O1 O -0.0165(3) 0.25381(9) 0.16971(13) 0.0208(5) Uani 1 1 d . . .
H1 H 0.077(5) 0.2800(15) 0.1611(19) 0.023(9) Uiso 1 1 d . . .
Br2 Br 0.77386(5) 0.886535(12) 0.131669(18) 0.01868(8) Uani 1 1 d . . .
C7 C 0.8497(4) 0.80040(12) 0.12273(17) 0.0151(6) Uani 1 1 d . . .
C8 C 1.0402(4) 0.78263(12) 0.08494(17) 0.0156(6) Uani 1 1 d . . .
C9 C 1.0958(4) 0.71984(12) 0.07614(17) 0.0164(6) Uani 1 1 d . . .
C10 C 0.9619(4) 0.67117(12) 0.10390(17) 0.0155(6) Uani 1 1 d . . .
C11 C 0.7715(4) 0.68965(12) 0.14198(17) 0.0159(6) Uani 1 1 d . . .
C12 C 0.7161(4) 0.75262(12) 0.15106(17) 0.0152(6) Uani 1 1 d . . .
F5 F 1.1765(3) 0.82716(7) 0.05636(10) 0.0233(4) Uani 1 1 d . . .
F6 F 1.2840(3) 0.70420(7) 0.03929(11) 0.0232(4) Uani 1 1 d . . .
F7 F 0.6369(3) 0.64401(7) 0.17030(11) 0.0231(4) Uani 1 1 d . . .
F8 F 0.5301(2) 0.76705(7) 0.18916(10) 0.0224(4) Uani 1 1 d . . .
O2 O 1.0252(3) 0.61023(9) 0.09327(13) 0.0203(5) Uani 1 1 d . . .
H2 H 0.929(6) 0.5894(17) 0.109(2) 0.042(12) Uiso 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.516(4) . ?
C13 S1 1.800(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 S2 1.800(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.516(4) . ?
C15 S2 1.803(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 S1 1.802(3) . ?
O3 S1 1.509(2) . ?
O4 S2 1.518(2) . ?
Br1 C1 1.869(3) . ?
C1 C2 1.386(4) . ?
C1 C6 1.382(4) . ?
C2 C3 1.372(4) . ?
C2 F1 1.349(3) . ?
C3 C4 1.391(4) . ?
C3 F2 1.344(3) . ?
C4 C5 1.385(4) . ?
C4 O1 1.341(3) . ?
C5 C6 1.372(4) . ?
C5 F3 1.356(3) . ?
C6 F4 1.346(3) . ?
O1 H1 0.80(3) . ?
Br2 C7 1.873(2) . ?
C7 C8 1.380(4) . ?
C7 C12 1.381(4) . ?
C8 C9 1.370(4) . ?
C8 F5 1.344(3) . ?
C9 C10 1.392(4) . ?
C9 F6 1.349(3) . ?
C10 C11 1.386(4) . ?
C10 O2 1.349(3) . ?
C11 C12 1.374(4) . ?
C11 F7 1.352(3) . ?
C12 F8 1.343(3) . ?
O2 H2 0.78(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
H13A C13 H13B 107.7 . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C14 C13 S1 113.88(19) . . ?
S1 C13 H13A 108.8 . . ?
S1 C13 H13B 108.8 . . ?
C13 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
C13 C14 S2 113.10(19) . . ?
H14A C14 H14B 107.8 . . ?
S2 C14 H14A 109.0 . . ?
S2 C14 H14B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C16 C15 S2 112.60(18) . . ?
S2 C15 H15A 109.1 . . ?
S2 C15 H15B 109.1 . . ?
C15 C16 H16A 108.7 . . ?
C15 C16 H16B 108.7 . . ?
C15 C16 S1 114.10(19) . . ?
H16A C16 H16B 107.6 . . ?
S1 C16 H16A 108.7 . . ?
S1 C16 H16B 108.7 . . ?
C13 S1 C16 99.34(12) . . ?
O3 S1 C13 103.82(12) . . ?
O3 S1 C16 105.82(12) . . ?
C14 S2 C15 97.72(12) . . ?
O4 S2 C14 105.10(12) . . ?
O4 S2 C15 104.74(12) . . ?
C2 C1 Br1 121.88(19) . . ?
C6 C1 Br1 121.2(2) . . ?
C6 C1 C2 116.9(2) . . ?
C3 C2 C1 121.8(2) . . ?
F1 C2 C1 119.7(2) . . ?
F1 C2 C3 118.4(2) . . ?
C2 C3 C4 121.5(2) . . ?
F2 C3 C2 119.3(2) . . ?
F2 C3 C4 119.3(2) . . ?
C5 C4 C3 116.2(2) . . ?
O1 C4 C3 118.6(2) . . ?
O1 C4 C5 125.2(2) . . ?
C6 C5 C4 122.4(2) . . ?
F3 C5 C4 118.8(2) . . ?
F3 C5 C6 118.9(2) . . ?
C5 C6 C1 121.2(2) . . ?
F4 C6 C1 120.1(2) . . ?
F4 C6 C5 118.7(2) . . ?
C4 O1 H1 109(2) . . ?
C8 C7 Br2 120.4(2) . . ?
C8 C7 C12 117.7(2) . . ?
C12 C7 Br2 121.9(2) . . ?
C9 C8 C7 121.3(2) . . ?
F5 C8 C7 120.2(2) . . ?
F5 C8 C9 118.5(2) . . ?
C8 C9 C10 121.6(2) . . ?
F6 C9 C8 119.7(2) . . ?
F6 C9 C10 118.6(2) . . ?
C11 C10 C9 116.5(2) . . ?
O2 C10 C9 118.9(2) . . ?
O2 C10 C11 124.6(2) . . ?
C12 C11 C10 121.9(2) . . ?
F7 C11 C10 118.6(2) . . ?
F7 C11 C12 119.6(2) . . ?
C11 C12 C7 121.0(2) . . ?
F8 C12 C7 120.3(2) . . ?
F8 C12 C11 118.7(2) . . ?
C10 O2 H2 106(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O3 0.80(3) 1.81(3) 2.569(3) 159(3) .
O2 H2 O4 0.78(3) 1.88(3) 2.595(3) 152(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
C13 C14 S2 C15 -62.4(2) . . . . ?
C13 C14 S2 O4 45.2(2) . . . . ?
C14 C13 S1 C16 -57.0(2) . . . . ?
C14 C13 S1 O3 52.0(2) . . . . ?
C15 C16 S1 C13 57.4(2) . . . . ?
C15 C16 S1 O3 -50.0(2) . . . . ?
C16 C15 S2 C14 62.2(2) . . . . ?
C16 C15 S2 O4 -45.7(2) . . . . ?
S1 C13 C14 S2 68.5(2) . . . . ?
S2 C15 C16 S1 -68.7(2) . . . . ?
Br1 C1 C2 C3 -180.0(2) . . . . ?
Br1 C1 C2 F1 0.7(4) . . . . ?
Br1 C1 C6 C5 178.4(2) . . . . ?
Br1 C1 C6 F4 -1.2(4) . . . . ?
C1 C2 C3 C4 1.6(4) . . . . ?
C1 C2 C3 F2 -178.6(2) . . . . ?
C2 C1 C6 C5 -1.7(4) . . . . ?
C2 C1 C6 F4 178.8(2) . . . . ?
C2 C3 C4 C5 -1.6(4) . . . . ?
C2 C3 C4 O1 177.7(2) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C3 C4 C5 F3 -179.8(2) . . . . ?
C4 C5 C6 C1 1.6(4) . . . . ?
C4 C5 C6 F4 -178.8(2) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
C6 C1 C2 F1 -179.2(2) . . . . ?
F1 C2 C3 C4 -179.1(2) . . . . ?
F1 C2 C3 F2 0.7(4) . . . . ?
F2 C3 C4 C5 178.5(2) . . . . ?
F2 C3 C4 O1 -2.1(4) . . . . ?
F3 C5 C6 C1 -178.6(2) . . . . ?
F3 C5 C6 F4 1.0(4) . . . . ?
O1 C4 C5 C6 -179.2(3) . . . . ?
O1 C4 C5 F3 0.9(4) . . . . ?
Br2 C7 C8 C9 -178.6(2) . . . . ?
Br2 C7 C8 F5 1.9(4) . . . . ?
Br2 C7 C12 C11 178.3(2) . . . . ?
Br2 C7 C12 F8 -2.6(4) . . . . ?
C7 C8 C9 C10 0.8(4) . . . . ?
C7 C8 C9 F6 -179.6(2) . . . . ?
C8 C7 C12 C11 0.1(4) . . . . ?
C8 C7 C12 F8 179.3(2) . . . . ?
C8 C9 C10 C11 -1.0(4) . . . . ?
C8 C9 C10 O2 179.8(3) . . . . ?
C9 C10 C11 C12 0.7(4) . . . . ?
C9 C10 C11 F7 -179.7(2) . . . . ?
C10 C11 C12 C7 -0.3(4) . . . . ?
C10 C11 C12 F8 -179.5(2) . . . . ?
C12 C7 C8 C9 -0.3(4) . . . . ?
C12 C7 C8 F5 -179.9(2) . . . . ?
F5 C8 C9 C10 -179.7(2) . . . . ?
F5 C8 C9 F6 -0.1(4) . . . . ?
F6 C9 C10 C11 179.5(2) . . . . ?
F6 C9 C10 O2 0.2(4) . . . . ?
F7 C11 C12 C7 -179.9(2) . . . . ?
F7 C11 C12 F8 0.9(4) . . . . ?
O2 C10 C11 C12 179.9(3) . . . . ?
O2 C10 C11 F7 -0.5(4) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 -1 1 0.0260 0.0003 -0.9994 1.0000 0.0168 -0.0529 -0.0036
0 1 -1 0.0360 -0.0003 0.9994 -1.0000 -0.0168 0.0529 0.0036
0 1 1 0.0157 0.0008 1.0012 0.9997 -0.0416 -0.0301 0.0215
0 -1 -1 0.0177 -0.0008 -1.0012 -0.9997 0.0416 0.0301 -0.0215
1 0 0 0.1526 1.0001 -0.0007 -0.0005 0.0466 -0.0025 0.1114
-1 0 0 0.1496 -1.0001 0.0007 0.0005 -0.0466 0.0025 -0.1114
_database_code_depnum_ccdc_archive 'CCDC 985846'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_dwb1227
_audit_creation_date             2012-04-30
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C6 H F4 I O), C4 H8 O S'
_chemical_formula_sum            'C16 H10 F8 I2 O3 S'
_chemical_formula_weight         688.10
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H9 F4 O1 I1 S1'
_chemical_oxdiff_usercomment     'Akihiro Takemura AT31A3'
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'
I I -0.4742 1.8119 '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'
S S 0.1246 0.1234 '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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   9.1682(14)
_cell_length_b                   9.4618(16)
_cell_length_c                   12.3198(16)
_cell_angle_alpha                75.183(14)
_cell_angle_beta                 74.084(13)
_cell_angle_gamma                79.202(14)
_cell_volume                     985.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5650
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      32.0753
_cell_measurement_theta_min      2.9270
_exptl_absorpt_coefficient_mu    3.387
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_recrystallization_method hexane
_exptl_crystal_size_max          0.1351
_exptl_crystal_size_mid          0.0888
_exptl_crystal_size_min          0.0562
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10138
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.15
_diffrn_reflns_theta_min         2.93
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -90.00  -45.00   1.0000   21.1700
omega____ theta____ kappa____ phi______ frames
    -      -25.1672  178.0000  150.0000 45

#__ type_ start__ end____ width___ exp.time_
  2 omega  -72.00  -46.00   1.0000   21.1700
omega____ theta____ kappa____ phi______ frames
    -      -25.1672  110.0000  -63.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   42.00   73.00   1.0000   21.1700
omega____ theta____ kappa____ phi______ frames
    -       26.4172 -110.0000 -157.0000 31

#__ type_ start__ end____ width___ exp.time_
  4 omega   28.00   73.00   1.0000   21.1700
omega____ theta____ kappa____ phi______ frames
    -       26.4172 -110.0000   63.0000 45

#__ type_ start__ end____ width___ exp.time_
  5 omega    7.00   93.00   1.0000   21.1700
omega____ theta____ kappa____ phi______ frames
    -       26.4172   57.0000 -180.0000 86

#__ type_ start__ end____ width___ exp.time_
  6 omega  -39.00   34.00   1.0000   21.1700
omega____ theta____ kappa____ phi______ frames
    -       26.4172  -57.0000  -60.0000 73

#__ type_ start__ end____ width___ exp.time_
  7 omega  -18.00   97.00   1.0000   21.1700
omega____ theta____ kappa____ phi______ frames
    -       26.4172   19.0000  120.0000 115
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0457922000
_diffrn_orient_matrix_UB_12      0.0584586000
_diffrn_orient_matrix_UB_13      -0.0211799000
_diffrn_orient_matrix_UB_21      -0.0112267000
_diffrn_orient_matrix_UB_22      0.0080138000
_diffrn_orient_matrix_UB_23      -0.0561578000
_diffrn_orient_matrix_UB_31      -0.0659994000
_diffrn_orient_matrix_UB_32      0.0512240000
_diffrn_orient_matrix_UB_33      0.0127694000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                5357
_reflns_number_total             6120
_reflns_odcompleteness_completeness 99.20
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_reflns_threshold_expression     >2sigma(I)
_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_collection       
;
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_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.871
_refine_diff_density_min         -0.733
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         6120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0254
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0148P)²+0.2966P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0517
_refine_ls_wR_factor_ref         0.0556
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I2 I 0.740904(17) 0.996598(18) 0.510045(13) 0.01844(4) Uani 1 1 d . . .
I1 I 0.221739(16) 1.545905(17) 1.043080(13) 0.01660(4) Uani 1 1 d . . .
S1 S 0.84328(6) 0.69306(7) 1.19936(5) 0.01636(11) Uani 1 1 d . . .
F1 F 0.56502(16) 1.30315(16) 1.35268(12) 0.0199(3) Uani 1 1 d . . .
F8 F 1.09721(16) 0.66085(16) 0.78548(13) 0.0209(3) Uani 1 1 d . . .
F2 F 0.36494(16) 1.51225(16) 1.26205(13) 0.0212(3) Uani 1 1 d . . .
F6 F 0.69737(16) 1.15803(17) 0.71880(13) 0.0242(3) Uani 1 1 d . . .
F4 F 0.56353(16) 1.01700(16) 1.09082(13) 0.0207(3) Uani 1 1 d . . .
F7 F 0.97309(17) 0.72401(17) 0.60294(13) 0.0231(3) Uani 1 1 d . . .
O2 O 1.0198(2) 0.8327(2) 0.94343(15) 0.0186(4) Uani 1 1 d . . .
C8 C 0.8550(3) 0.9982(3) 0.8303(2) 0.0160(5) Uani 1 1 d . . .
C1 C 0.5746(2) 1.1567(3) 1.22076(19) 0.0131(4) Uani 1 1 d . . .
C6 C 0.5190(2) 1.1420(3) 1.1304(2) 0.0141(4) Uani 1 1 d . . .
C14 C 0.6188(3) 0.6706(3) 1.3929(2) 0.0234(5) Uani 1 1 d . . .
H14A H 0.6020 0.7744 1.4005 0.028 Uiso 1 1 calc R . .
H14B H 0.5278 0.6226 1.4400 0.028 Uiso 1 1 calc R . .
C12 C 0.9954(2) 0.7825(2) 0.7707(2) 0.0144(4) Uani 1 1 d . . .
C2 C 0.5176(3) 1.2844(3) 1.26338(19) 0.0138(4) Uani 1 1 d . . .
C15 C 0.7614(3) 0.5898(3) 1.4318(2) 0.0292(6) Uani 1 1 d . . .
H15A H 0.7662 0.4822 1.4402 0.035 Uiso 1 1 calc R . .
H15B H 0.7619 0.6091 1.5069 0.035 Uiso 1 1 calc R . .
C3 C 0.4148(3) 1.3923(3) 1.2154(2) 0.0142(4) Uani 1 1 d . . .
C11 C 0.9323(3) 0.8166(3) 0.6767(2) 0.0151(4) Uani 1 1 d . . .
C4 C 0.3652(2) 1.3796(2) 1.1225(2) 0.0131(4) Uani 1 1 d . . .
C13 C 0.6477(3) 0.6624(3) 1.2671(2) 0.0210(5) Uani 1 1 d . . .
H13A H 0.5774 0.7386 1.2284 0.025 Uiso 1 1 calc R . .
H13B H 0.6306 0.5645 1.2617 0.025 Uiso 1 1 calc R . .
C10 C 0.8301(3) 0.9429(3) 0.6556(2) 0.0153(4) Uani 1 1 d . . .
C9 C 0.7937(3) 1.0331(3) 0.7350(2) 0.0162(5) Uani 1 1 d . . .
C5 C 0.4189(2) 1.2511(3) 1.08163(19) 0.0135(4) Uani 1 1 d . . .
C7 C 0.9566(2) 0.8714(3) 0.8518(2) 0.0145(4) Uani 1 1 d . . .
C16 C 0.8968(3) 0.6490(3) 1.3376(2) 0.0236(5) Uani 1 1 d . . .
H16A H 0.9881 0.5740 1.3359 0.028 Uiso 1 1 calc R . .
H16B H 0.9213 0.7385 1.3531 0.028 Uiso 1 1 calc R . .
F3 F 0.37342(16) 1.23060(16) 0.99247(12) 0.0206(3) Uani 1 1 d . . .
O3 O 0.84666(18) 0.85918(19) 1.15501(15) 0.0181(3) Uani 1 1 d . . .
F5 F 0.81530(16) 1.08787(17) 0.90535(13) 0.0223(3) Uani 1 1 d . . .
O1 O 0.67436(19) 1.0554(2) 1.26955(15) 0.0178(4) Uani 1 1 d . . .
H1 H 0.721(4) 0.991(4) 1.233(3) 0.037(9) Uiso 1 1 d . . .
H2 H 0.973(4) 0.862(4) 0.997(3) 0.034(10) Uiso 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I2 C10 2.079(2) . ?
I1 C4 2.075(2) . ?
S1 C13 1.802(2) . ?
S1 C16 1.825(3) . ?
S1 O3 1.5296(19) . ?
F1 C2 1.350(2) . ?
F8 C12 1.346(2) . ?
F2 C3 1.350(2) . ?
F6 C9 1.343(3) . ?
F4 C6 1.344(2) . ?
F7 C11 1.353(3) . ?
O2 C7 1.346(3) . ?
O2 H2 0.77(3) . ?
C8 C9 1.378(3) . ?
C8 C7 1.390(3) . ?
C8 F5 1.345(3) . ?
C1 C6 1.392(3) . ?
C1 C2 1.395(3) . ?
C1 O1 1.340(3) . ?
C6 C5 1.378(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.518(4) . ?
C14 C13 1.519(4) . ?
C12 C11 1.374(3) . ?
C12 C7 1.398(3) . ?
C2 C3 1.384(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.530(4) . ?
C3 C4 1.381(3) . ?
C11 C10 1.389(3) . ?
C4 C5 1.388(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C10 C9 1.392(3) . ?
C5 F3 1.345(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
O1 H1 0.83(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
C13 S1 C16 92.87(12) . . ?
O3 S1 C13 107.85(11) . . ?
O3 S1 C16 105.46(12) . . ?
C7 O2 H2 116(2) . . ?
C9 C8 C7 121.6(2) . . ?
F5 C8 C9 119.6(2) . . ?
F5 C8 C7 118.8(2) . . ?
C6 C1 C2 116.5(2) . . ?
O1 C1 C6 124.1(2) . . ?
O1 C1 C2 119.4(2) . . ?
F4 C6 C1 118.7(2) . . ?
F4 C6 C5 119.5(2) . . ?
C5 C6 C1 121.8(2) . . ?
H14A C14 H14B 108.7 . . ?
C15 C14 H14A 110.6 . . ?
C15 C14 H14B 110.6 . . ?
C15 C14 C13 105.6(2) . . ?
C13 C14 H14A 110.6 . . ?
C13 C14 H14B 110.6 . . ?
F8 C12 C11 119.5(2) . . ?
F8 C12 C7 119.0(2) . . ?
C11 C12 C7 121.6(2) . . ?
F1 C2 C1 119.08(19) . . ?
F1 C2 C3 119.51(19) . . ?
C3 C2 C1 121.4(2) . . ?
C14 C15 H15A 110.5 . . ?
C14 C15 H15B 110.5 . . ?
C14 C15 C16 106.0(2) . . ?
H15A C15 H15B 108.7 . . ?
C16 C15 H15A 110.5 . . ?
C16 C15 H15B 110.5 . . ?
F2 C3 C2 117.6(2) . . ?
F2 C3 C4 120.6(2) . . ?
C4 C3 C2 121.7(2) . . ?
F7 C11 C12 118.3(2) . . ?
F7 C11 C10 119.9(2) . . ?
C12 C11 C10 121.8(2) . . ?
C3 C4 I1 122.26(16) . . ?
C3 C4 C5 117.0(2) . . ?
C5 C4 I1 120.75(17) . . ?
S1 C13 H13A 110.3 . . ?
S1 C13 H13B 110.3 . . ?
C14 C13 S1 107.30(18) . . ?
C14 C13 H13A 110.3 . . ?
C14 C13 H13B 110.3 . . ?
H13A C13 H13B 108.5 . . ?
C11 C10 I2 121.41(17) . . ?
C11 C10 C9 116.7(2) . . ?
C9 C10 I2 121.91(17) . . ?
F6 C9 C8 118.6(2) . . ?
F6 C9 C10 119.7(2) . . ?
C8 C9 C10 121.7(2) . . ?
C6 C5 C4 121.6(2) . . ?
F3 C5 C6 118.32(19) . . ?
F3 C5 C4 120.1(2) . . ?
O2 C7 C8 123.8(2) . . ?
O2 C7 C12 119.5(2) . . ?
C8 C7 C12 116.6(2) . . ?
S1 C16 H16A 110.1 . . ?
S1 C16 H16B 110.1 . . ?
C15 C16 S1 107.84(19) . . ?
C15 C16 H16A 110.1 . . ?
C15 C16 H16B 110.1 . . ?
H16A C16 H16B 108.5 . . ?
C1 O1 H1 116(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O3 0.83(3) 1.81(3) 2.636(2) 172(3) .
O2 H2 O3 0.77(3) 1.96(3) 2.701(2) 159(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
I2 C10 C9 F6 0.6(3) . . . . ?
I2 C10 C9 C8 -178.94(19) . . . . ?
I1 C4 C5 C6 177.43(18) . . . . ?
I1 C4 C5 F3 -2.6(3) . . . . ?
F1 C2 C3 F2 -0.7(3) . . . . ?
F1 C2 C3 C4 178.7(2) . . . . ?
F8 C12 C11 F7 1.3(3) . . . . ?
F8 C12 C11 C10 -178.1(2) . . . . ?
F8 C12 C7 O2 -0.9(3) . . . . ?
F8 C12 C7 C8 177.9(2) . . . . ?
F2 C3 C4 I1 3.3(3) . . . . ?
F2 C3 C4 C5 -178.4(2) . . . . ?
F4 C6 C5 C4 177.5(2) . . . . ?
F4 C6 C5 F3 -2.4(3) . . . . ?
F7 C11 C10 I2 -1.4(3) . . . . ?
F7 C11 C10 C9 -179.9(2) . . . . ?
C1 C6 C5 C4 -1.9(4) . . . . ?
C1 C6 C5 F3 178.2(2) . . . . ?
C1 C2 C3 F2 179.8(2) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C6 C1 C2 F1 178.6(2) . . . . ?
C6 C1 C2 C3 -1.9(3) . . . . ?
C14 C15 C16 S1 -33.0(3) . . . . ?
C12 C11 C10 I2 178.00(18) . . . . ?
C12 C11 C10 C9 -0.5(4) . . . . ?
C2 C1 C6 F4 -176.1(2) . . . . ?
C2 C1 C6 C5 3.2(3) . . . . ?
C2 C3 C4 I1 -176.12(18) . . . . ?
C2 C3 C4 C5 2.2(4) . . . . ?
C15 C14 C13 S1 -41.2(3) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
C3 C4 C5 F3 179.0(2) . . . . ?
C11 C12 C7 O2 179.1(2) . . . . ?
C11 C12 C7 C8 -2.0(4) . . . . ?
C11 C10 C9 F6 179.0(2) . . . . ?
C11 C10 C9 C8 -0.5(4) . . . . ?
C13 S1 C16 C15 8.1(2) . . . . ?
C13 C14 C15 C16 47.4(3) . . . . ?
C9 C8 C7 O2 179.8(2) . . . . ?
C9 C8 C7 C12 1.1(4) . . . . ?
C7 C8 C9 F6 -179.4(2) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C7 C12 C11 F7 -178.8(2) . . . . ?
C7 C12 C11 C10 1.8(4) . . . . ?
C16 S1 C13 C14 19.0(2) . . . . ?
O3 S1 C13 C14 -88.24(19) . . . . ?
O3 S1 C16 C15 117.50(19) . . . . ?
F5 C8 C9 F6 1.2(4) . . . . ?
F5 C8 C9 C10 -179.3(2) . . . . ?
F5 C8 C7 O2 -0.7(4) . . . . ?
F5 C8 C7 C12 -179.4(2) . . . . ?
O1 C1 C6 F4 2.1(4) . . . . ?
O1 C1 C6 C5 -178.6(2) . . . . ?
O1 C1 C2 F1 0.3(3) . . . . ?
O1 C1 C2 C3 179.8(2) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1 -2 -3 0.0351 0.9998 -2.0002 -3.0001 -0.0076 0.1412 -0.2068
2 0 3 0.0478 2.0001 0.0001 3.0000 0.0281 -0.1909 -0.0937
1 1 0 0.0235 1.0000 1.0000 -0.0000 0.1042 -0.0032 -0.0148
1 -2 0 0.0359 1.0000 -2.0000 -0.0000 -0.0711 -0.0273 -0.1684
-2 3 4 0.0491 -1.9997 3.0002 4.0001 -0.0009 -0.1781 0.3367
-5 4 -1 0.0653 -4.9999 4.0001 -0.9999 0.0261 0.1443 0.5221
-2 1 -1 0.0660 -2.0000 1.0000 -1.0000 -0.0119 0.0866 0.1705
-2 -1 0 0.0332 -2.0000 -0.9999 0.0001 -0.1500 0.0144 0.0808
-4 -2 1 0.0315 -3.9999 -1.9998 1.0002 -0.3213 -0.0273 0.1743
2 -1 -4 0.0325 1.9998 -1.0002 -4.0001 0.1178 0.1942 -0.2343
0 -4 -3 0.0336 -0.0002 -4.0001 -3.0000 -0.1703 0.1364 -0.2432
0 -1 -2 0.0267 -0.0001 -1.0001 -2.0000 -0.0161 0.1043 -0.0768
-3 -4 -2 0.0214 -3.0001 -4.0000 -1.9999 -0.3289 0.1139 -0.0324
0 -1 5 0.0476 0.0002 -0.9998 5.0001 -0.1643 -0.2888 0.0126
_database_code_depnum_ccdc_archive 'CCDC 985847'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_dwb1215
_audit_creation_date             2013-08-23
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C6 H F4 I O, C10 H8 N2'
_chemical_formula_sum            'C16 H9 F4 I N2 O'
_chemical_formula_weight         448.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H9 F4 I1 N2 O1'
_chemical_oxdiff_usercomment     'Akihiro Takemura AT27-B3'
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'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   16.0299(11)
_cell_length_b                   4.0059(2)
_cell_length_c                   25.154(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.546(9)
_cell_angle_gamma                90.00
_cell_volume                     1548.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1807
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      27.9910
_cell_measurement_theta_min      3.5260
_exptl_absorpt_coefficient_mu    2.118
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.709
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.922
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.2442
_exptl_crystal_size_mid          0.0622
_exptl_crystal_size_min          0.0253
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            4832
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         3.26
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector_area_resol_mean 16.1450
_diffrn_measured_fraction_theta_full 0.9928
_diffrn_measured_fraction_theta_max 0.9928
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -13.00   25.00   1.0000  140.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.1611  -99.0000 -180.0000 38

#__ type_ start__ end____ width___ exp.time_
  2 omega   59.00   88.00   1.0000  140.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4111  178.0000  150.0000 29

#__ type_ start__ end____ width___ exp.time_
  3 omega  -14.00   57.00   1.0000  140.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4111  -99.0000  -30.0000 71

#__ type_ start__ end____ width___ exp.time_
  4 omega  -27.00   43.00   1.0000  140.0000
omega____ theta____ kappa____ phi______ frames
    -       16.4111   19.0000 -150.0000 70
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0298450000
_diffrn_orient_matrix_UB_12      0.0747222000
_diffrn_orient_matrix_UB_13      0.0125491000
_diffrn_orient_matrix_UB_21      -0.0087977000
_diffrn_orient_matrix_UB_22      0.1269109000
_diffrn_orient_matrix_UB_23      -0.0204771000
_diffrn_orient_matrix_UB_31      -0.0340654000
_diffrn_orient_matrix_UB_32      -0.0982161000
_diffrn_orient_matrix_UB_33      -0.0170048000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2443
_reflns_number_total             2738
_reflns_odcompleteness_completeness 99.28
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.04
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         1.648
_refine_diff_density_min         -1.952
_refine_diff_density_rms         0.179
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.325
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2738
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0651
_refine_ls_restrained_S_all      1.323
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0139P)²+15.1259P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1267
_refine_special_details          
;
The crystal showed evidence of non-merohedral twinning but use of CrysAlisPro to resolve this as a two component system gave a lower quality final structure than using a non-twinned model due to the predominance of overlapping reflections.
The OH hydrogen was located by difference map and allowed to refine. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C5) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.005
Uanis(C4) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7219(5) 0.345(2) 0.3744(3) 0.015(2) Uani 1 1 d . . .
C2 C 0.7130(5) 0.322(2) 0.3182(3) 0.017(2) Uani 1 1 d . . .
C3 C 0.7745(5) 0.169(2) 0.2980(3) 0.0139(19) Uani 1 1 d . . .
C4 C 0.8477(5) 0.015(2) 0.3332(3) 0.0106(17) Uani 1 1 d U . .
C5 C 0.8570(5) 0.039(2) 0.3891(3) 0.0142(18) Uani 1 1 d U . .
C6 C 0.7951(5) 0.199(2) 0.4093(3) 0.0149(19) Uani 1 1 d . . .
C7 C 0.4214(5) 0.956(2) 0.3714(3) 0.019(2) Uani 1 1 d . . .
H7 H 0.4514 0.9685 0.3448 0.023 Uiso 1 1 calc R . .
C8 C 0.3380(5) 1.088(2) 0.3584(3) 0.018(2) Uani 1 1 d . . .
H8 H 0.3133 1.1869 0.3240 0.021 Uiso 1 1 calc R . .
C9 C 0.2919(5) 1.071(2) 0.3975(3) 0.0123(18) Uani 1 1 d . . .
C10 C 0.3324(5) 0.922(2) 0.4480(3) 0.0165(19) Uani 1 1 d . . .
H10 H 0.3039 0.9061 0.4753 0.020 Uiso 1 1 calc R . .
C11 C 0.4161(5) 0.799(3) 0.4572(4) 0.021(2) Uani 1 1 d . . .
H11 H 0.4426 0.7006 0.4913 0.025 Uiso 1 1 calc R . .
C12 C 0.2025(5) 1.214(2) 0.3857(3) 0.0129(18) Uani 1 1 d . . .
C13 C 0.1486(5) 1.241(2) 0.3317(3) 0.016(2) Uani 1 1 d . . .
H13 H 0.1666 1.1583 0.3022 0.019 Uiso 1 1 calc R . .
C14 C 0.0683(5) 1.391(2) 0.3222(3) 0.018(2) Uani 1 1 d . . .
H14 H 0.0331 1.4066 0.2858 0.022 Uiso 1 1 calc R . .
C15 C 0.0887(5) 1.482(2) 0.4148(3) 0.017(2) Uani 1 1 d . . .
H15 H 0.0683 1.5604 0.4436 0.020 Uiso 1 1 calc R . .
C16 C 0.1703(5) 1.335(2) 0.4273(3) 0.016(2) Uani 1 1 d . . .
H16 H 0.2037 1.3183 0.4641 0.020 Uiso 1 1 calc R . .
F1 F 0.6439(3) 0.4587(15) 0.28120(19) 0.0272(13) Uani 1 1 d . . .
F2 F 0.7628(3) 0.1536(14) 0.24293(18) 0.0225(13) Uani 1 1 d . . .
F3 F 0.9271(3) -0.1010(14) 0.42575(19) 0.0225(13) Uani 1 1 d . . .
F4 F 0.8088(3) 0.2031(15) 0.46460(18) 0.0243(13) Uani 1 1 d . . .
I1 I 0.62289(3) 0.54679(15) 0.40315(2) 0.01616(19) Uani 1 1 d . . .
N1 N 0.4610(4) 0.813(2) 0.4199(3) 0.0171(17) Uani 1 1 d . . .
N2 N 0.0384(4) 1.5136(19) 0.3625(3) 0.0139(16) Uani 1 1 d . . .
O1 O 0.9039(4) -0.1410(16) 0.3107(2) 0.0163(14) Uani 1 1 d . . .
H1 H 0.939(8) -0.27(3) 0.333(5) 0.07(4) Uiso 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.381(11) . ?
C1 C6 1.380(11) . ?
C1 I1 2.086(8) . ?
C2 C3 1.377(11) . ?
C2 F1 1.343(9) . ?
C3 C4 1.398(11) . ?
C3 F2 1.345(9) . ?
C4 C5 1.374(11) . ?
C4 O1 1.346(9) . ?
C5 C6 1.392(11) . ?
C5 F3 1.355(9) . ?
C6 F4 1.346(9) . ?
C7 H7 0.9300 . ?
C7 C8 1.387(11) . ?
C7 N1 1.333(11) . ?
C8 H8 0.9300 . ?
C8 C9 1.390(11) . ?
C9 C10 1.385(11) . ?
C9 C12 1.494(11) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(11) . ?
C11 H11 0.9300 . ?
C11 N1 1.337(11) . ?
C12 C13 1.392(11) . ?
C12 C16 1.379(11) . ?
C13 H13 0.9300 . ?
C13 C14 1.378(11) . ?
C14 H14 0.9300 . ?
C14 N2 1.332(10) . ?
C15 H15 0.9300 . ?
C15 C16 1.386(11) . ?
C15 N2 1.341(10) . ?
C16 H16 0.9300 . ?
O1 H1 0.85(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 I1 120.9(6) . . ?
C6 C1 C2 116.4(7) . . ?
C6 C1 I1 122.5(6) . . ?
C3 C2 C1 122.1(8) . . ?
F1 C2 C1 120.4(7) . . ?
F1 C2 C3 117.4(7) . . ?
C2 C3 C4 121.5(7) . . ?
F2 C3 C2 119.8(7) . . ?
F2 C3 C4 118.6(7) . . ?
C5 C4 C3 116.4(7) . . ?
O1 C4 C3 118.6(7) . . ?
O1 C4 C5 125.0(7) . . ?
C4 C5 C6 121.6(7) . . ?
F3 C5 C4 119.6(7) . . ?
F3 C5 C6 118.8(7) . . ?
C1 C6 C5 121.9(7) . . ?
F4 C6 C1 120.7(7) . . ?
F4 C6 C5 117.4(7) . . ?
C8 C7 H7 118.1 . . ?
N1 C7 H7 118.1 . . ?
N1 C7 C8 123.8(8) . . ?
C7 C8 H8 120.5 . . ?
C7 C8 C9 118.9(8) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 C12 120.9(7) . . ?
C10 C9 C8 117.8(7) . . ?
C10 C9 C12 121.3(7) . . ?
C9 C10 H10 120.5 . . ?
C9 C10 C11 119.0(8) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 H11 118.1 . . ?
N1 C11 C10 123.8(8) . . ?
N1 C11 H11 118.1 . . ?
C13 C12 C9 121.1(7) . . ?
C16 C12 C9 122.0(7) . . ?
C16 C12 C13 116.9(8) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.4(8) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 118.3 . . ?
N2 C14 C13 123.4(8) . . ?
N2 C14 H14 118.3 . . ?
C16 C15 H15 119.0 . . ?
N2 C15 H15 119.0 . . ?
N2 C15 C16 121.9(8) . . ?
C12 C16 C15 120.6(8) . . ?
C12 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C7 N1 C11 116.6(7) . . ?
C14 N2 C15 117.7(7) . . ?
C4 O1 H1 113(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
C1 C2 C3 C4 2.7(14) . . . . ?
C1 C2 C3 F2 -179.9(8) . . . . ?
C2 C1 C6 C5 0.5(14) . . . . ?
C2 C1 C6 F4 -178.8(8) . . . . ?
C2 C3 C4 C5 -3.0(13) . . . . ?
C2 C3 C4 O1 177.8(8) . . . . ?
C3 C4 C5 C6 2.1(13) . . . . ?
C3 C4 C5 F3 -179.3(8) . . . . ?
C4 C5 C6 C1 -1.0(14) . . . . ?
C4 C5 C6 F4 178.3(8) . . . . ?
C6 C1 C2 C3 -1.3(14) . . . . ?
C6 C1 C2 F1 -179.7(8) . . . . ?
C7 C8 C9 C10 0.4(14) . . . . ?
C7 C8 C9 C12 178.9(8) . . . . ?
C8 C7 N1 C11 0.1(14) . . . . ?
C8 C9 C10 C11 -0.2(14) . . . . ?
C8 C9 C12 C13 27.2(13) . . . . ?
C8 C9 C12 C16 -150.8(9) . . . . ?
C9 C10 C11 N1 -0.1(15) . . . . ?
C9 C12 C13 C14 -176.6(8) . . . . ?
C9 C12 C16 C15 176.8(8) . . . . ?
C10 C9 C12 C13 -154.3(9) . . . . ?
C10 C9 C12 C16 27.7(14) . . . . ?
C10 C11 N1 C7 0.1(14) . . . . ?
C12 C9 C10 C11 -178.7(8) . . . . ?
C12 C13 C14 N2 -0.1(14) . . . . ?
C13 C12 C16 C15 -1.3(13) . . . . ?
C13 C14 N2 C15 -1.6(14) . . . . ?
C16 C12 C13 C14 1.5(13) . . . . ?
C16 C15 N2 C14 1.8(13) . . . . ?
F1 C2 C3 C4 -178.9(8) . . . . ?
F1 C2 C3 F2 -1.4(13) . . . . ?
F2 C3 C4 C5 179.5(8) . . . . ?
F2 C3 C4 O1 0.2(12) . . . . ?
F3 C5 C6 C1 -179.5(8) . . . . ?
F3 C5 C6 F4 -0.2(13) . . . . ?
I1 C1 C2 C3 -175.2(7) . . . . ?
I1 C1 C2 F1 6.4(12) . . . . ?
I1 C1 C6 C5 174.2(7) . . . . ?
I1 C1 C6 F4 -5.1(12) . . . . ?
N1 C7 C8 C9 -0.4(15) . . . . ?
N2 C15 C16 C12 -0.4(14) . . . . ?
O1 C4 C5 C6 -178.6(8) . . . . ?
O1 C4 C5 F3 -0.1(13) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1 0 -1 0.0264 -0.9912 0.0020 -1.0130 0.0170 0.0297 0.0508
0 1 0 0.1225 0.0046 1.0020 0.0241 0.0750 0.1266 -0.0990
0 -1 0 0.1215 -0.0046 -1.0020 -0.0241 -0.0750 -0.1266 0.0990
0 0 3 0.0091 -0.0176 -0.0023 3.0070 0.0381 -0.0617 -0.0503
0 0 -3 0.0161 0.0176 0.0023 -3.0070 -0.0381 0.0617 0.0503
1 0 1 0.0010 0.9912 -0.0020 1.0130 -0.0170 -0.0297 -0.0508



_database_code_depnum_ccdc_archive 'CCDC 985848'
