#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:58:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180325 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/39/7153930.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_7153930
loop_
_publ_author_name
'Stephens, David E.'
'Chavez, Gabriel'
'Valdes, Martin'
'Dovalina, Monica'
'Arman, Hadi D.'
'Larionov, Oleg V.'
_publ_section_title
;
 Synthetic and mechanistic aspects of the regioselective base-mediated
 reaction of perfluoroalkyl- and perfluoroarylsilanes with heterocyclic
 N-oxides.
;
_journal_issue                   32
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6190
_journal_page_last               6199
_journal_paper_doi               10.1039/c4ob01088d
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C13 H14 Cl N O S'
_chemical_formula_sum            'C13 H14 Cl N O S'
_chemical_formula_weight         267.76
_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                 90.530(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1435(17)
_cell_length_b                   6.0132(11)
_cell_length_c                   23.209(5)
_cell_measurement_reflns_used    6668
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      40.2
_cell_measurement_theta_min      2.2
_cell_volume                     1276.0(4)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r5 (Rigaku, 2010)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      98(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Saturn724 (2x2 bin mode)
;
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7393
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.23
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.445
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2513
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0372
_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)+(0.0632P)²+0.6000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1019
_reflns_number_gt                2348
_reflns_number_total             2513
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob01088d2.cif
_cod_data_source_block           cd1221a
_cod_depositor_comments          'Adding full bibliography for 7153930.cif.'
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7153930
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
Cl1 Cl -0.37582(5) -0.28153(7) 0.00745(2) 0.03125(16) Uani 1 1 d
S1 S -0.00177(4) 0.67920(7) 0.109234(17) 0.02229(15) Uani 1 1 d
O1 O -0.50343(14) 0.1590(3) 0.19098(6) 0.0341(3) Uani 1 1 d
N1 N -0.39553(15) 0.2771(3) 0.17175(6) 0.0237(3) Uani 1 1 d
C1 C -0.31124(18) -0.0477(3) 0.04368(7) 0.0224(3) Uani 1 1 d
C2 C -0.19283(19) 0.0708(3) 0.02042(7) 0.0231(4) Uani 1 1 d
C3 C -0.14001(18) 0.2538(3) 0.04877(7) 0.0209(3) Uani 1 1 d
C4 C -0.20391(17) 0.3291(3) 0.10063(7) 0.0181(3) Uani 1 1 d
C5 C -0.15488(18) 0.5217(3) 0.13168(7) 0.0199(3) Uani 1 1 d
C6 C -0.23356(19) 0.5862(3) 0.17886(7) 0.0236(4) Uani 1 1 d
C7 C -0.35341(19) 0.4637(3) 0.19834(7) 0.0260(4) Uani 1 1 d
C8 C -0.32418(18) 0.2072(3) 0.12176(7) 0.0198(3) Uani 1 1 d
C9 C -0.37738(18) 0.0163(3) 0.09347(7) 0.0225(4) Uani 1 1 d
C10 C 0.15210(19) 0.5535(3) 0.15106(7) 0.0228(4) Uani 1 1 d
C11 C 0.1584(2) 0.3020(3) 0.14257(9) 0.0296(4) Uani 1 1 d
C12 C 0.2868(2) 0.6664(3) 0.12601(9) 0.0304(4) Uani 1 1 d
C13 C 0.1382(2) 0.6101(4) 0.21471(8) 0.0313(4) Uani 1 1 d
H7A H -0.406(3) 0.500(4) 0.2297(10) 0.038 Uiso 1 1 d
H6A H -0.206(3) 0.718(4) 0.1999(10) 0.038 Uiso 1 1 d
H3A H -0.063(3) 0.333(4) 0.0341(10) 0.038 Uiso 1 1 d
H2A H -0.148(3) 0.027(4) -0.0147(10) 0.038 Uiso 1 1 d
H9A H -0.460(3) -0.060(4) 0.1098(10) 0.038 Uiso 1 1 d
H11A H 0.244(3) 0.240(4) 0.1626(12) 0.047 Uiso 1 1 d
H11B H 0.176(3) 0.263(4) 0.1015(12) 0.047 Uiso 1 1 d
H11C H 0.071(3) 0.232(4) 0.1611(11) 0.047 Uiso 1 1 d
H13A H 0.050(3) 0.548(4) 0.2311(11) 0.047 Uiso 1 1 d
H13B H 0.226(3) 0.547(4) 0.2349(11) 0.047 Uiso 1 1 d
H13C H 0.129(3) 0.768(4) 0.2206(11) 0.047 Uiso 1 1 d
H12A H 0.282(3) 0.832(5) 0.1301(11) 0.047 Uiso 1 1 d
H12B H 0.369(3) 0.616(4) 0.1462(11) 0.047 Uiso 1 1 d
H12C H 0.300(3) 0.634(4) 0.0855(12) 0.047 Uiso 1 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.1484 0.1585 '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'
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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C5 S1 C10 103.00(8)
O1 N1 C7 121.17(15)
O1 N1 C8 118.81(15)
C7 N1 C8 120.02(15)
C9 C1 C2 122.05(16)
C9 C1 Cl1 119.09(13)
C2 C1 Cl1 118.86(13)
C3 C2 C1 119.47(16)
C3 C2 H2A 119.0(14)
C1 C2 H2A 121.6(14)
C2 C3 C4 121.28(15)
C2 C3 H3A 120.6(15)
C4 C3 H3A 118.1(15)
C8 C4 C3 117.20(15)
C8 C4 C5 119.04(15)
C3 C4 C5 123.75(15)
C6 C5 C4 117.75(15)
C6 C5 S1 120.34(13)
C4 C5 S1 121.87(12)
C5 C6 C7 121.83(16)
C5 C6 H6A 120.2(14)
C7 C6 H6A 118.0(14)
N1 C7 C6 121.09(16)
N1 C7 H7A 114.9(15)
C6 C7 H7A 124.0(15)
N1 C8 C9 118.01(15)
N1 C8 C4 120.11(15)
C9 C8 C4 121.88(15)
C1 C9 C8 118.11(15)
C1 C9 H9A 123.7(14)
C8 C9 H9A 118.2(14)
C13 C10 C12 110.19(15)
C13 C10 C11 110.50(16)
C12 C10 C11 111.11(16)
C13 C10 S1 110.24(13)
C12 C10 S1 103.26(12)
C11 C10 S1 111.35(12)
C10 C11 H11A 110.4(15)
C10 C11 H11B 111.3(15)
H11A C11 H11B 103(2)
C10 C11 H11C 109.3(15)
H11A C11 H11C 106(2)
H11B C11 H11C 117(2)
C10 C12 H12A 111.8(14)
C10 C12 H12B 108.2(15)
H12A C12 H12B 108(2)
C10 C12 H12C 112.9(15)
H12A C12 H12C 107(2)
H12B C12 H12C 108(2)
C10 C13 H13A 111.9(15)
C10 C13 H13B 107.1(14)
H13A C13 H13B 110(2)
C10 C13 H13C 111.5(16)
H13A C13 H13C 105(2)
H13B C13 H13C 112(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.7390(17)
S1 C5 1.7724(17)
S1 C10 1.8622(17)
O1 N1 1.298(2)
N1 C7 1.336(2)
N1 C8 1.401(2)
C1 C9 1.365(2)
C1 C2 1.408(2)
C2 C3 1.368(2)
C2 H2A 0.95(2)
C3 C4 1.417(2)
C3 H3A 0.92(2)
C4 C8 1.413(2)
C4 C5 1.434(2)
C5 C6 1.372(2)
C6 C7 1.399(3)
C6 H6A 0.96(2)
C7 H7A 0.90(2)
C8 C9 1.407(2)
C9 H9A 0.96(2)
C10 C13 1.522(2)
C10 C12 1.526(2)
C10 C11 1.527(2)
C11 H11A 0.98(3)
C11 H11B 1.00(3)
C11 H11C 1.00(3)
C12 H12A 1.00(3)
C12 H12B 0.93(3)
C12 H12C 0.97(3)
C13 H13A 0.97(3)
C13 H13B 1.00(3)
C13 H13C 0.96(3)
