#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/76/1507647.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_1507647
loop_
_publ_author_name
'Keceli, Gizem'
'Toscano, John P.'
_publ_section_title
;
 Reactivity of nitroxyl-derived sulfinamides.
;
_journal_issue                   20
_journal_name_full               Biochemistry
_journal_page_first              4206
_journal_page_last               4216
_journal_paper_doi               10.1021/bi300015u
_journal_volume                  51
_journal_year                    2012
_chemical_formula_moiety         'C8 H11 N O S'
_chemical_formula_sum            'C8 H11 N O S'
_chemical_formula_weight         169.24
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.094(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.9432(7)
_cell_length_b                   5.24461(18)
_cell_length_c                   11.9405(5)
_cell_measurement_reflns_used    3020
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      26.28
_cell_measurement_theta_min      1.76
_cell_volume                     843.04(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 15.989
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Goniometer KM4/Xcalibur, detector: Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5149
_diffrn_reflns_theta_full        26.24
_diffrn_reflns_theta_max         26.24
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.324
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
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            colorless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thick lath'
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     106
_refine_ls_number_reflns         1708
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0311
_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)+(0.0440P)²+0.4157P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0866
_reflns_number_gt                1505
_reflns_number_total             1708
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi300015u_si_002.cif
_cod_data_source_block           x0859a
_cod_original_cell_volume        843.04(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1507647
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 0.43008(3) 0.41829(7) 0.32906(3) 0.01456(14) Uani 1 1 d .
C1 C 0.39118(11) 0.1367(3) 0.39224(13) 0.0157(3) Uani 1 1 d .
H1A H 0.4312 -0.0108 0.3791 0.019 Uiso 1 1 calc R
H1B H 0.4035 0.1612 0.4770 0.019 Uiso 1 1 calc R
C2 C 0.28141(11) 0.0793(3) 0.34041(14) 0.0189(3) Uani 1 1 d .
H2A H 0.2697 0.0536 0.2558 0.023 Uiso 1 1 calc R
H2B H 0.2646 -0.0819 0.3740 0.023 Uiso 1 1 calc R
C3 C 0.21263(10) 0.2872(3) 0.36115(13) 0.0178(3) Uani 1 1 d .
C4 C 0.20440(12) 0.3369(3) 0.47312(14) 0.0237(4) Uani 1 1 d .
H4 H 0.2427 0.2407 0.5366 0.028 Uiso 1 1 calc R
C5 C 0.14091(12) 0.5252(4) 0.49265(15) 0.0273(4) Uani 1 1 d .
H5 H 0.1361 0.5573 0.5693 0.033 Uiso 1 1 calc R
C6 C 0.08437(11) 0.6668(3) 0.40107(15) 0.0243(4) Uani 1 1 d .
H6 H 0.0405 0.7949 0.4147 0.029 Uiso 1 1 calc R
C7 C 0.09216(11) 0.6207(3) 0.29002(15) 0.0226(4) Uani 1 1 d .
H7 H 0.0538 0.7177 0.2269 0.027 Uiso 1 1 calc R
C8 C 0.15615(11) 0.4321(3) 0.27021(14) 0.0201(3) Uani 1 1 d .
H8 H 0.1612 0.4021 0.1935 0.024 Uiso 1 1 calc R
N1 N 0.55017(9) 0.3756(3) 0.38572(11) 0.0173(3) Uani 1 1 d D
H1C H 0.5806(13) 0.506(4) 0.3680(15) 0.021 Uiso 1 1 d D
H1D H 0.5723(13) 0.227(4) 0.3719(15) 0.021 Uiso 1 1 d D
O1 O 0.40042(8) 0.3673(2) 0.19996(9) 0.0179(2) Uani 1 1 d .
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 111.89(6)
O1 S1 C1 104.42(7)
N1 S1 C1 95.79(7)
C2 C1 S1 111.79(10)
C2 C1 H1A 109.3
S1 C1 H1A 109.3
C2 C1 H1B 109.3
S1 C1 H1B 109.3
H1A C1 H1B 107.9
C3 C2 C1 113.78(12)
C3 C2 H2A 108.8
C1 C2 H2A 108.8
C3 C2 H2B 108.8
C1 C2 H2B 108.8
H2A C2 H2B 107.7
C8 C3 C4 118.37(14)
C8 C3 C2 121.33(14)
C4 C3 C2 120.30(14)
C5 C4 C3 120.64(15)
C5 C4 H4 119.7
C3 C4 H4 119.7
C6 C5 C4 120.42(15)
C6 C5 H5 119.8
C4 C5 H5 119.8
C7 C6 C5 119.56(16)
C7 C6 H6 120.2
C5 C6 H6 120.2
C6 C7 C8 120.13(15)
C6 C7 H7 119.9
C8 C7 H7 119.9
C3 C8 C7 120.88(15)
C3 C8 H8 119.6
C7 C8 H8 119.6
S1 N1 H1C 107.6(12)
S1 N1 H1D 114.6(12)
H1C N1 H1D 116.4(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.5122(11)
S1 N1 1.6498(13)
S1 C1 1.8048(15)
C1 C2 1.524(2)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.514(2)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C8 1.390(2)
C3 C4 1.396(2)
C4 C5 1.386(2)
C4 H4 0.9500
C5 C6 1.386(2)
C5 H5 0.9500
C6 C7 1.380(2)
C6 H6 0.9500
C7 C8 1.393(2)
C7 H7 0.9500
C8 H8 0.9500
N1 H1C 0.861(17)
N1 H1D 0.869(17)
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
N1 H1C O1 0.861(17) 2.103(18) 2.9220(17) 158.6(16) 2_655
N1 H1D O1 0.869(17) 2.148(18) 2.9992(18) 166.3(16) 2_645
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 C1 C2 -54.64(12)
N1 S1 C1 C2 -169.04(11)
S1 C1 C2 C3 -62.04(15)
C1 C2 C3 C8 112.93(16)
C1 C2 C3 C4 -67.30(18)
C8 C3 C4 C5 0.4(2)
C2 C3 C4 C5 -179.38(15)
C3 C4 C5 C6 0.1(3)
C4 C5 C6 C7 -0.5(3)
C5 C6 C7 C8 0.3(2)
C4 C3 C8 C7 -0.6(2)
C2 C3 C8 C7 179.17(14)
C6 C7 C8 C3 0.3(2)
