#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/84/4028400.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_4028400
loop_
_publ_author_name
'Miroslav Kavala'
'Roman Boča'
'Lubomír Dlháň'
'Vlasta Brezová'
'Martin Breza'
'Jozef Kožíšek'
'Marek Fronc'
'Peter Herich'
'Lubomír Švorc'
'Peter Szolcsányi'
_publ_section_title
;
 Preparation and Spectroscopic, Magnetic, and Electrochemical Studies of
 Mono-/Biradical TEMPO Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6558
_journal_page_last               6569
_journal_paper_doi               10.1021/jo400845m
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C10 H20 N O4 S'
_chemical_formula_weight         250.33
_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                 113.437(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.9484(6)
_cell_length_b                   9.9797(3)
_cell_length_c                   11.1310(4)
_cell_measurement_reflns_used    8020
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4967
_cell_measurement_theta_min      3.6557
_cell_volume                     1319.69(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1998)'
_computing_publication_material  ' enCIFer (Allen et al., 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4340
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_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  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0148
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21523
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.56
_diffrn_reflns_theta_min         3.66
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_correction_T_min  0.859
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
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            red
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.853
_exptl_crystal_size_mid          0.477
_exptl_crystal_size_min          0.420
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0141(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         3391
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0405
_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)+(0.0519P)²+0.4112P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1126
_reflns_number_gt                2807
_reflns_number_total             3391
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400845m_si_002.cif
_cod_data_source_block           C10H20NO4S
_cod_original_cell_volume        1319.69(9)
_cod_original_sg_symbol_Hall     '-p 2ybc'
_cod_database_code               4028400
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
C1 C 0.08289(12) 0.54078(15) 0.78647(16) 0.0456(3) Uani 1 1 d .
C2 C 0.11385(12) 0.46331(16) 0.68712(16) 0.0478(4) Uani 1 1 d .
H2B H 0.0845 0.3729 0.6797 0.057 Uiso 1 1 calc R
H2A H 0.0783 0.5058 0.6021 0.057 Uiso 1 1 calc R
C3 C 0.23898(12) 0.45672(14) 0.72376(13) 0.0386(3) Uani 1 1 d .
H3A H 0.2769 0.4129 0.8089 0.046 Uiso 1 1 calc R
C4 C 0.28287(12) 0.59702(15) 0.72685(15) 0.0440(3) Uani 1 1 d .
H4B H 0.2434 0.6388 0.6422 0.053 Uiso 1 1 calc R
H4A H 0.3622 0.5932 0.7431 0.053 Uiso 1 1 calc R
C5 C 0.26766(12) 0.68240(15) 0.83271(15) 0.0432(3) Uani 1 1 d .
C6 C -0.04085(14) 0.5809(2) 0.7231(2) 0.0705(6) Uani 1 1 d .
H6C H -0.0607 0.6295 0.7853 0.085 Uiso 1 1 calc R
H6B H -0.0866 0.5019 0.6959 0.085 Uiso 1 1 calc R
H6A H -0.0531 0.6366 0.6484 0.085 Uiso 1 1 calc R
C7 C 0.10300(19) 0.4576(2) 0.9086(2) 0.0678(5) Uani 1 1 d .
H7C H 0.0832 0.5094 0.9690 0.081 Uiso 1 1 calc R
H7B H 0.1810 0.4329 0.9491 0.081 Uiso 1 1 calc R
H7A H 0.0575 0.3782 0.8846 0.081 Uiso 1 1 calc R
C8 C 0.28325(16) 0.82962(17) 0.8078(2) 0.0664(5) Uani 1 1 d .
H8C H 0.2735 0.8835 0.8739 0.080 Uiso 1 1 calc R
H8B H 0.2286 0.8550 0.7232 0.080 Uiso 1 1 calc R
H8A H 0.3576 0.8431 0.8105 0.080 Uiso 1 1 calc R
C9 C 0.35167(15) 0.6421(2) 0.96956(17) 0.0618(5) Uani 1 1 d .
H9C H 0.3401 0.6969 1.0340 0.074 Uiso 1 1 calc R
H9B H 0.4270 0.6545 0.9753 0.074 Uiso 1 1 calc R
H9A H 0.3405 0.5497 0.9851 0.074 Uiso 1 1 calc R
N1 N 0.15049(10) 0.66712(13) 0.82505(13) 0.0436(3) Uani 1 1 d .
O1 O 0.12038(10) 0.75020(13) 0.89264(14) 0.0638(4) Uani 1 1 d .
O2 O 0.25314(9) 0.37756(11) 0.61897(10) 0.0476(3) Uani 1 1 d .
C10 C 0.35455(19) 0.16028(19) 0.74038(18) 0.0651(5) Uani 1 1 d .
H10C H 0.4207 0.1058 0.7631 0.078 Uiso 1 1 calc R
H10B H 0.2893 0.1084 0.6894 0.078 Uiso 1 1 calc R
H10A H 0.3480 0.1908 0.8188 0.078 Uiso 1 1 calc R
O4 O 0.35684(12) 0.25132(15) 0.52513(12) 0.0663(4) Uani 1 1 d .
O5 O 0.45839(10) 0.37734(14) 0.72707(14) 0.0675(4) Uani 1 1 d .
S1 S 0.36471(3) 0.29789(4) 0.64936(4) 0.04570(14) 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
N1 C1 C7 109.25(14)
N1 C1 C6 107.36(13)
C7 C1 C6 109.30(15)
N1 C1 C2 110.00(12)
C7 C1 C2 111.66(13)
C6 C1 C2 109.16(14)
C3 C2 C1 112.93(12)
O2 C3 C4 110.52(11)
O2 C3 C2 105.49(11)
C4 C3 C2 108.72(12)
C3 C4 C5 111.88(12)
N1 C5 C8 107.06(12)
N1 C5 C4 109.78(11)
C8 C5 C4 109.28(14)
N1 C5 C9 109.47(13)
C8 C5 C9 109.95(15)
C4 C5 C9 111.21(13)
O1 N1 C5 116.12(12)
O1 N1 C1 115.73(12)
C5 N1 C1 124.56(12)
C3 O2 S1 119.64(8)
O5 S1 O4 119.22(8)
O5 S1 O2 109.87(7)
O4 S1 O2 104.65(7)
O5 S1 C10 109.26(10)
O4 S1 C10 108.35(9)
O2 S1 C10 104.45(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.4970(19)
C1 C7 1.524(2)
C1 C6 1.525(2)
C1 C2 1.528(2)
C2 C3 1.507(2)
C3 O2 1.4793(16)
C3 C4 1.506(2)
C4 C5 1.529(2)
C5 N1 1.4932(18)
C5 C8 1.523(2)
C5 C9 1.532(2)
N1 O1 1.2801(17)
O2 S1 1.5636(11)
C10 S1 1.7424(19)
O4 S1 1.4235(12)
O5 S1 1.4190(13)
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
N1 C1 C2 C3 44.50(17)
C7 C1 C2 C3 -76.98(17)
C6 C1 C2 C3 162.05(14)
C1 C2 C3 O2 179.25(12)
C1 C2 C3 C4 -62.20(16)
O2 C3 C4 C5 179.03(11)
C2 C3 C4 C5 63.69(16)
C3 C4 C5 N1 -47.68(16)
C3 C4 C5 C8 -164.81(13)
C3 C4 C5 C9 73.62(16)
C8 C5 N1 O1 -49.85(19)
C4 C5 N1 O1 -168.37(13)
C9 C5 N1 O1 69.29(18)
C8 C5 N1 C1 152.49(16)
C4 C5 N1 C1 33.97(19)
C9 C5 N1 C1 -88.37(17)
C7 C1 N1 O1 -67.12(17)
C6 C1 N1 O1 51.31(19)
C2 C1 N1 O1 169.98(13)
C7 C1 N1 C5 90.62(17)
C6 C1 N1 C5 -150.95(16)
C2 C1 N1 C5 -32.28(19)
C4 C3 O2 S1 89.06(13)
C2 C3 O2 S1 -153.60(10)
C3 O2 S1 O5 -42.43(13)
C3 O2 S1 O4 -171.55(11)
C3 O2 S1 C10 74.66(12)
