#------------------------------------------------------------------------------
#$Date: 2017-10-13 01:32:00 +0200 (vie 13 de oct de 2017) $
#$Revision: 201954 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/62/1506275.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1506275
loop_
_publ_author_name
'Xu, Wei'
'Abboud, Khalil A.'
'Ghiviriga, Ion'
'Dolbier, Jr, William R'
'Rapp, Magdalena'
'Wnuk, Stanislaw F.'
_publ_section_title
;
 An unexpected reaction of trimethylsilyl fluorosulfonyldifluoroacetate
 (TFDA) with imidazoles. Formation of N-difluoromethylthioureas.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              5549
_journal_page_last               5551
_journal_paper_doi               10.1021/ol062213k
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C11 H10 F N S'
_chemical_formula_weight         207.26
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.819(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.5663(5)
_cell_length_b                   7.9830(6)
_cell_length_c                   20.8615(17)
_cell_measurement_reflns_used    93
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.0
_cell_volume                     1080.61(15)
_computing_cell_refinement
'Bruker SMART v5.624 & SAINT 6.36a (Bruker 1998)'
_computing_data_collection       'Bruker SMART v5.624 (Bruker 1998)'
_computing_data_reduction        'Bruker SHELXTL v6.14 (Bruker 2000)'
_computing_molecular_graphics    'Bruker SHELXTL v6.14'
_computing_publication_material  'Bruker SHELXTL v6.14'
_computing_structure_refinement  'Bruker SHELXTL v6.14'
_computing_structure_solution    'Bruker SHELXTL v6.14'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'SMART CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            6489
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.98
_diffrn_standards_decay_%        1
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  0.9639
_exptl_absorpt_correction_T_min  0.9262
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
'based on measured indexed crystal faces, Bruker SHELXTL  v6.12 (Bruker 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         2393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0365
_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)+(0.0548P)²+0.4381P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1089
_reflns_number_gt                2125
_reflns_number_total             2393
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ol062213ksi20060906_032230.cif
_cod_data_source_block           xu03
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1506275
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
S1 S 0.68803(6) 0.22695(5) 0.03973(2) 0.02953(15) Uani 1 1 d .
F1 F 0.81844(19) 0.76506(12) 0.05684(6) 0.0394(3) Uani 1 1 d .
F2 F 0.6768(2) 0.63221(16) 0.12839(6) 0.0535(4) Uani 1 1 d .
N1 N 0.9226(2) 0.50118(15) 0.08139(6) 0.0237(3) Uani 1 1 d .
N2 N 1.0967(2) 0.27038(16) 0.08730(6) 0.0228(3) Uani 1 1 d .
C1 C 0.9037(2) 0.33195(19) 0.06956(7) 0.0219(3) Uani 1 1 d .
C2 C 1.1254(3) 0.5414(2) 0.10720(8) 0.0281(3) Uani 1 1 d .
H2 H 1.159(3) 0.646(3) 0.1181(10) 0.040(6) Uiso 1 1 d .
C3 C 1.2319(3) 0.3988(2) 0.11045(8) 0.0276(3) Uani 1 1 d .
H3 H 1.374(4) 0.382(3) 0.1228(10) 0.040(6) Uiso 1 1 d .
C4 C 0.7519(3) 0.6134(2) 0.07244(8) 0.0293(4) Uani 1 1 d .
H4A H 0.6421 0.5715 0.0376 0.035 Uiso 1 1 calc R
C5 C 1.1565(3) 0.09458(19) 0.08108(7) 0.0257(3) Uani 1 1 d .
H5A H 1.2784 0.0898 0.0585 0.031 Uiso 1 1 calc R
H5B H 1.0426 0.0343 0.0540 0.031 Uiso 1 1 calc R
C6 C 1.2067(2) 0.00674(18) 0.14570(7) 0.0228(3) Uani 1 1 d .
C7 C 1.0554(3) -0.0146(2) 0.18523(8) 0.0308(4) Uani 1 1 d .
H7A H 0.9222 0.0321 0.1727 0.037 Uiso 1 1 calc R
C8 C 1.0991(3) -0.1036(2) 0.24269(8) 0.0358(4) Uani 1 1 d .
H8A H 0.9959 -0.1172 0.2696 0.043 Uiso 1 1 calc R
C9 C 1.2921(3) -0.1728(2) 0.26103(8) 0.0345(4) Uani 1 1 d .
H9A H 1.3209 -0.2345 0.3003 0.041 Uiso 1 1 calc R
C10 C 1.4433(3) -0.1525(2) 0.22233(8) 0.0329(4) Uani 1 1 d .
H10A H 1.5760 -0.2000 0.2351 0.040 Uiso 1 1 calc R
C11 C 1.4013(3) -0.0623(2) 0.16464(8) 0.0272(3) Uani 1 1 d .
H11A H 1.5056 -0.0479 0.1382 0.033 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0237(2) 0.0243(2) 0.0392(3) -0.00372(16) 0.00023(17) -0.00237(14)
F1 0.0472(7) 0.0209(5) 0.0489(7) 0.0075(4) 0.0032(5) 0.0036(4)
F2 0.0636(8) 0.0509(7) 0.0529(7) 0.0111(6) 0.0311(6) 0.0277(6)
N1 0.0236(6) 0.0183(6) 0.0285(6) -0.0014(5) 0.0023(5) 0.0005(5)
N2 0.0223(7) 0.0201(6) 0.0259(6) -0.0002(5) 0.0038(5) 0.0027(5)
C1 0.0249(8) 0.0195(7) 0.0219(7) 0.0008(5) 0.0057(6) 0.0013(6)
C2 0.0281(8) 0.0228(8) 0.0323(8) -0.0017(6) 0.0016(6) -0.0043(6)
C3 0.0224(8) 0.0277(8) 0.0318(8) 0.0004(6) 0.0013(6) -0.0026(6)
C4 0.0334(9) 0.0201(7) 0.0339(8) 0.0017(6) 0.0037(7) 0.0045(6)
C5 0.0309(8) 0.0206(7) 0.0257(7) -0.0016(6) 0.0053(6) 0.0054(6)
C6 0.0266(8) 0.0168(7) 0.0245(7) -0.0027(6) 0.0022(6) 0.0011(6)
C7 0.0276(8) 0.0344(9) 0.0309(8) -0.0004(7) 0.0064(7) 0.0049(7)
C8 0.0379(10) 0.0420(10) 0.0296(8) 0.0015(7) 0.0117(7) -0.0025(8)
C9 0.0433(10) 0.0340(9) 0.0245(7) 0.0041(7) -0.0005(7) -0.0025(8)
C10 0.0292(8) 0.0350(9) 0.0319(8) 0.0008(7) -0.0039(7) 0.0043(7)
C11 0.0254(8) 0.0261(8) 0.0301(8) -0.0016(6) 0.0047(6) 0.0007(6)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C2 110.47(13)
C1 N1 C4 123.13(13)
C2 N1 C4 126.24(13)
C1 N2 C3 110.30(13)
C1 N2 C5 124.99(14)
C3 N2 C5 124.68(13)
N2 C1 N1 104.59(13)
N2 C1 S1 128.24(12)
N1 C1 S1 127.17(12)
C3 C2 N1 106.62(14)
C3 C2 H2 133.0(15)
N1 C2 H2 120.3(14)
C2 C3 N2 108.02(14)
C2 C3 H3 128.8(13)
N2 C3 H3 123.0(13)
F2 C4 F1 106.63(14)
F2 C4 N1 110.04(13)
F1 C4 N1 108.66(14)
F2 C4 H4A 110.5
F1 C4 H4A 110.5
N1 C4 H4A 110.5
N2 C5 C6 112.93(12)
N2 C5 H5A 109.0
C6 C5 H5A 109.0
N2 C5 H5B 109.0
C6 C5 H5B 109.0
H5A C5 H5B 107.8
C11 C6 C7 119.32(14)
C11 C6 C5 120.15(14)
C7 C6 C5 120.42(14)
C8 C7 C6 120.15(16)
C8 C7 H7A 119.9
C6 C7 H7A 119.9
C9 C8 C7 120.27(16)
C9 C8 H8A 119.9
C7 C8 H8A 119.9
C8 C9 C10 120.13(16)
C8 C9 H9A 119.9
C10 C9 H9A 119.9
C9 C10 C11 120.04(16)
C9 C10 H10A 120.0
C11 C10 H10A 120.0
C6 C11 C10 120.09(16)
C6 C11 H11A 120.0
C10 C11 H11A 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.6807(16)
F1 C4 1.3437(19)
F2 C4 1.343(2)
N1 C1 1.3754(19)
N1 C2 1.395(2)
N1 C4 1.425(2)
N2 C1 1.357(2)
N2 C3 1.393(2)
N2 C5 1.4684(19)
C2 C3 1.332(2)
C2 H2 0.88(2)
C3 H3 0.94(2)
C4 H4A 1.0000
C5 C6 1.510(2)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C11 1.392(2)
C6 C7 1.395(2)
C7 C8 1.385(2)
C7 H7A 0.9500
C8 C9 1.382(3)
C8 H8A 0.9500
C9 C10 1.382(3)
C9 H9A 0.9500
C10 C11 1.393(2)
C10 H10A 0.9500
C11 H11A 0.9500
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 21151861 ChemSpider
