#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/27/4022744.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_4022744
loop_
_publ_author_name
'Michael Harmata'
'Pinguan Zheng'
'Chaofeng Huang'
'Maria G. Gomes'
'Weijiang Ying'
'Kanok-On Ranyanil'
'Gayatri Balan'
'Nathan L. Calkins'
_publ_section_title
;
 Expedient Synthesis of Sulfinamides from Sulfonyl Chlorides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              683
_journal_page_last               685
_journal_paper_doi               10.1021/jo062296i
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C14 H15 N O2 S2'
_chemical_formula_weight         293.39
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 111.5060(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.4928(6)
_cell_length_b                   8.2280(5)
_cell_length_c                   9.8444(6)
_cell_measurement_reflns_used    3353
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      2.2
_cell_volume                     715.38(8)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5183
_diffrn_reflns_theta_full        27.09
_diffrn_reflns_theta_max         27.09
_diffrn_reflns_theta_min         2.22
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    0.369
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Data were corrected for decay and absorption using the program SADABS 
 (Sheldrick, G. M. (2003). SADABS. Version 2.10. University of
 Göttingen, Germany).
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2960
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0314
_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)+(0.0451P)²+0.0582P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0804
_reflns_number_gt                2762
_reflns_number_total             2960
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062296isi20061106_074721.cif
_cod_data_source_block           PZ-VI-152-c3
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4022744
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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 0.68674(5) 0.32434(6) 0.21808(5) 0.02624(13) Uani 1 1 d .
O1 O 0.76713(19) 0.2149(2) 0.33539(18) 0.0398(4) Uani 1 1 d .
N1 N 0.51619(19) 0.2944(2) 0.13199(19) 0.0299(4) Uani 1 1 d .
C1 C 0.7248(2) 0.5243(3) 0.2868(2) 0.0248(4) Uani 1 1 d .
S2 S 0.39459(6) 0.36019(7) 0.20859(6) 0.03097(14) Uani 1 1 d .
O2 O 0.27611(18) 0.4532(2) 0.0950(2) 0.0428(4) Uani 1 1 d .
C2 C 0.8222(2) 0.5467(3) 0.4300(2) 0.0283(5) Uani 1 1 d .
H2 H 0.8673 0.4563 0.4903 0.034 Uiso 1 1 calc R
C3 C 0.8524(3) 0.7041(3) 0.4832(2) 0.0336(5) Uani 1 1 d .
H3 H 0.9178 0.7218 0.5815 0.040 Uiso 1 1 calc R
C4 C 0.7886(2) 0.8345(3) 0.3950(3) 0.0359(5) Uani 1 1 d .
H4 H 0.8103 0.9416 0.4328 0.043 Uiso 1 1 calc R
C5 C 0.6930(2) 0.8112(3) 0.2513(3) 0.0346(5) Uani 1 1 d .
H5 H 0.6508 0.9022 0.1907 0.042 Uiso 1 1 calc R
C6 C 0.6589(3) 0.6551(3) 0.1959(2) 0.0309(5) Uani 1 1 d .
H6 H 0.5921 0.6378 0.0981 0.037 Uiso 1 1 calc R
C7 C 0.7620(2) 0.3125(3) 0.0794(3) 0.0376(5) Uani 1 1 d .
H7A H 0.8719 0.3290 0.1217 0.056 Uiso 1 1 calc R
H7B H 0.7160 0.3967 0.0061 0.056 Uiso 1 1 calc R
H7C H 0.7402 0.2052 0.0331 0.056 Uiso 1 1 calc R
C8 C 0.3103(2) 0.1669(3) 0.2181(2) 0.0285(5) Uani 1 1 d .
C9 C 0.3987(2) 0.0450(3) 0.3058(3) 0.0357(5) Uani 1 1 d .
H9 H 0.5040 0.0617 0.3567 0.043 Uiso 1 1 calc R
C10 C 0.3322(3) -0.1010(3) 0.3186(3) 0.0365(5) Uani 1 1 d .
H10 H 0.3930 -0.1850 0.3776 0.044 Uiso 1 1 calc R
C11 C 0.1770(2) -0.1271(3) 0.2462(2) 0.0320(5) Uani 1 1 d .
C12 C 0.0910(2) -0.0027(3) 0.1599(2) 0.0332(5) Uani 1 1 d .
H12 H -0.0146 -0.0184 0.1097 0.040 Uiso 1 1 calc R
C13 C 0.1561(3) 0.1441(3) 0.1453(2) 0.0314(5) Uani 1 1 d .
H13 H 0.0956 0.2282 0.0861 0.038 Uiso 1 1 calc R
C14 C 0.1061(3) -0.2874(3) 0.2609(3) 0.0425(6) Uani 1 1 d .
H14A H -0.0041 -0.2748 0.2278 0.064 Uiso 1 1 calc R
H14B H 0.1458 -0.3218 0.3634 0.064 Uiso 1 1 calc R
H14C H 0.1306 -0.3697 0.2011 0.064 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O1 S1 N1 118.65(10)
O1 S1 C7 109.90(11)
N1 S1 C7 101.96(10)
O1 S1 C1 107.52(10)
N1 S1 C1 112.60(10)
C7 S1 C1 105.33(11)
S1 N1 S2 117.08(11)
C2 C1 C6 121.7(2)
C2 C1 S1 118.71(17)
C6 C1 S1 119.59(16)
O2 S2 N1 106.54(10)
O2 S2 C8 105.54(10)
N1 S2 C8 97.47(9)
C1 C2 C3 118.5(2)
C1 C2 H2 120.8
C3 C2 H2 120.8
C4 C3 C2 120.5(2)
C4 C3 H3 119.7
C2 C3 H3 119.7
C3 C4 C5 120.6(2)
C3 C4 H4 119.7
C5 C4 H4 119.7
C4 C5 C6 120.1(2)
C4 C5 H5 120.0
C6 C5 H5 120.0
C5 C6 C1 118.6(2)
C5 C6 H6 120.7
C1 C6 H6 120.7
S1 C7 H7A 109.5
S1 C7 H7B 109.5
H7A C7 H7B 109.5
S1 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C13 C8 C9 120.5(2)
C13 C8 S2 119.88(18)
C9 C8 S2 119.53(16)
C10 C9 C8 119.5(2)
C10 C9 H9 120.3
C8 C9 H9 120.3
C9 C10 C11 121.1(2)
C9 C10 H10 119.4
C11 C10 H10 119.4
C12 C11 C10 118.2(2)
C12 C11 C14 121.3(2)
C10 C11 C14 120.5(2)
C11 C12 C13 121.4(2)
C11 C12 H12 119.3
C13 C12 H12 119.3
C8 C13 C12 119.3(2)
C8 C13 H13 120.3
C12 C13 H13 120.3
C11 C14 H14A 109.5
C11 C14 H14B 109.5
H14A C14 H14B 109.5
C11 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4423(17)
S1 N1 1.5473(17)
S1 C7 1.761(2)
S1 C1 1.765(2)
N1 S2 1.6829(18)
C1 C2 1.386(3)
C1 C6 1.393(3)
S2 O2 1.4759(17)
S2 C8 1.798(2)
C2 C3 1.387(3)
C2 H2 0.9500
C3 C4 1.374(3)
C3 H3 0.9500
C4 C5 1.385(3)
C4 H4 0.9500
C5 C6 1.386(3)
C5 H5 0.9500
C6 H6 0.9500
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 C13 1.387(3)
C8 C9 1.387(3)
C9 C10 1.384(3)
C9 H9 0.9500
C10 C11 1.398(3)
C10 H10 0.9500
C11 C12 1.388(3)
C11 C14 1.512(4)
C12 C13 1.388(4)
C12 H12 0.9500
C13 H13 0.9500
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
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
O1 S1 N1 S2 80.59(15)
C7 S1 N1 S2 -158.61(13)
C1 S1 N1 S2 -46.22(15)
O1 S1 C1 C2 1.98(18)
N1 S1 C1 C2 134.52(16)
C7 S1 C1 C2 -115.19(18)
O1 S1 C1 C6 -179.13(17)
N1 S1 C1 C6 -46.60(19)
C7 S1 C1 C6 63.69(19)
S1 N1 S2 O2 130.70(13)
S1 N1 S2 C8 -120.59(13)
C6 C1 C2 C3 0.8(3)
S1 C1 C2 C3 179.64(16)
C1 C2 C3 C4 -0.9(3)
C2 C3 C4 C5 0.0(3)
C3 C4 C5 C6 1.0(3)
C4 C5 C6 C1 -1.1(3)
C2 C1 C6 C5 0.2(3)
S1 C1 C6 C5 -178.63(16)
O2 S2 C8 C13 -10.31(19)
N1 S2 C8 C13 -119.86(17)
O2 S2 C8 C9 173.77(17)
N1 S2 C8 C9 64.23(19)
C13 C8 C9 C10 1.0(3)
S2 C8 C9 C10 176.89(18)
C8 C9 C10 C11 -0.9(3)
C9 C10 C11 C12 0.5(3)
C9 C10 C11 C14 179.8(2)
C10 C11 C12 C13 -0.1(3)
C14 C11 C12 C13 -179.5(2)
C9 C8 C13 C12 -0.7(3)
S2 C8 C13 C12 -176.54(17)
C11 C12 C13 C8 0.2(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9544788
