#------------------------------------------------------------------------------
#$Date: 2018-09-26 06:29:44 +0300 (Wed, 26 Sep 2018) $
#$Revision: 211175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/26/8102624.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_8102624
loop_
_publ_author_name
'Carolin Lauf'
'Clemens Bruhn'
'Herbert Frauenrath'
_publ_section_title
;
 Crystal structure of N-tosyl-2-methylserine, C11H15NO5S
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              139
_journal_volume                  225
_journal_year                    2010
_chemical_formula_moiety         'C11 H15 N O5 S'
_chemical_formula_sum            'C11 H15 N O5 S'
_chemical_formula_weight         273.30
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 112.716(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2184(9)
_cell_length_b                   10.1462(6)
_cell_length_c                   13.1829(12)
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.61
_cell_measurement_theta_min      2.16
_cell_volume                     1260.76(19)
_computing_molecular_graphics    'ORTEP-3 [3]'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997) [4]'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990) [4]'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      ' 180 frames, detector distance = 135 mm'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, multiple pinhole'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0166
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7892
_diffrn_reflns_theta_full        25.16
_diffrn_reflns_theta_max         25.16
_diffrn_reflns_theta_min         2.16
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           30
_diffrn_source_power             1.50
_diffrn_source_voltage           50
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_correction_T_min  0.9443
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'X-red ver. 1.31 (Stoe & Cie. 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2231
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0305
_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)+(0.0464P)²+0.4945P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0829
_refine_ls_wR_factor_ref         0.0848
_reflns_number_gt                1999
_reflns_number_total             2231
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2861.cff
_cod_data_source_block           i0646
_cod_original_cell_volume        1260.76(18)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8102624
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.27694(17) 0.22598(15) -0.07287(13) 0.0295(3) Uani 1 1 d . . .
C2 C 0.19011(18) 0.30487(17) -0.15915(14) 0.0341(4) Uani 1 1 d . . .
H2A H 0.1150 0.3543 -0.1523 0.041 Uiso 1 1 calc R . .
C3 C 0.21541(19) 0.3099(2) -0.25557(15) 0.0412(4) Uani 1 1 d . . .
H3A H 0.1572 0.3641 -0.3145 0.049 Uiso 1 1 calc R . .
C4 C 0.3251(2) 0.2365(2) -0.26758(15) 0.0442(5) Uani 1 1 d . . .
C5 C 0.4108(2) 0.1599(2) -0.17960(18) 0.0484(5) Uani 1 1 d . . .
H5A H 0.4860 0.1102 -0.1862 0.058 Uiso 1 1 calc R . .
C6 C 0.3886(2) 0.15487(18) -0.08245(16) 0.0418(4) Uani 1 1 d . . .
H6A H 0.4491 0.1032 -0.0226 0.050 Uiso 1 1 calc R . .
C7 C 0.3490(3) 0.2413(3) -0.37407(19) 0.0693(7) Uani 1 1 d . . .
H7C H 0.3702 0.1525 -0.3927 0.083 Uiso 1 1 calc R . .
H7B H 0.4288 0.3000 -0.3652 0.083 Uiso 1 1 calc R . .
H7A H 0.2632 0.2745 -0.4332 0.083 Uiso 1 1 calc R . .
C8 C 0.31236(16) 0.45311(15) 0.14263(12) 0.0286(3) Uani 1 1 d . . .
C9 C 0.22574(17) 0.57953(16) 0.13563(12) 0.0293(3) Uani 1 1 d . . .
C10 C 0.39547(19) 0.41940(17) 0.26503(14) 0.0364(4) Uani 1 1 d . . .
H10B H 0.4464 0.3349 0.2710 0.044 Uiso 1 1 calc R . .
H10A H 0.4666 0.4890 0.2998 0.044 Uiso 1 1 calc R . .
C11 C 0.41963(17) 0.47656(18) 0.08852(15) 0.0368(4) Uani 1 1 d . . .
H11C H 0.4768 0.3969 0.0956 0.044 Uiso 1 1 calc R . .
H11B H 0.4819 0.5503 0.1251 0.044 Uiso 1 1 calc R . .
H11A H 0.3685 0.4974 0.0105 0.044 Uiso 1 1 calc R . .
N1 N 0.20640(15) 0.34862(14) 0.08720(11) 0.0288(3) Uani 1 1 d . . .
H1 H 0.125(2) 0.3740(19) 0.0534(16) 0.035 Uiso 1 1 d . . .
O1 O 0.11542(13) 0.12794(12) 0.01993(9) 0.0383(3) Uani 1 1 d . . .
O2 O 0.37145(13) 0.15729(12) 0.13273(10) 0.0407(3) Uani 1 1 d . . .
O3 O 0.09765(12) 0.58529(12) 0.09202(10) 0.0389(3) Uani 1 1 d . . .
O4 O 0.31035(14) 0.67963(12) 0.18307(11) 0.0409(3) Uani 1 1 d . . .
H4 H 0.257(2) 0.762(2) 0.1764(17) 0.049 Uiso 1 1 d . . .
O5 O 0.30144(14) 0.40917(12) 0.32068(10) 0.0396(3) Uani 1 1 d . . .
H5 H 0.328(2) 0.460(2) 0.3729(19) 0.047 Uiso 1 1 d . . .
S1 S 0.24271(4) 0.20663(4) 0.04888(3) 0.02994(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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.52(16) . . ?
C2 C1 S1 120.95(13) . . ?
C6 C1 S1 118.45(13) . . ?
C3 C2 C1 118.81(16) . . ?
C3 C2 H2A 120.6 . . ?
C1 C2 H2A 120.6 . . ?
C2 C3 C4 121.42(17) . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
C5 C4 C3 118.37(17) . . ?
C5 C4 C7 121.1(2) . . ?
C3 C4 C7 120.6(2) . . ?
C6 C5 C4 121.12(18) . . ?
C6 C5 H5A 119.4 . . ?
C4 C5 H5A 119.4 . . ?
C5 C6 C1 119.73(18) . . ?
C5 C6 H6A 120.1 . . ?
C1 C6 H6A 120.1 . . ?
C4 C7 H7C 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7C C7 H7B 109.5 . . ?
C4 C7 H7A 109.5 . . ?
H7C C7 H7A 109.5 . . ?
H7B C7 H7A 109.5 . . ?
N1 C8 C11 113.29(13) . . ?
N1 C8 C9 105.74(12) . . ?
C11 C8 C9 109.81(13) . . ?
N1 C8 C10 110.93(13) . . ?
C11 C8 C10 108.40(13) . . ?
C9 C8 C10 108.57(13) . . ?
O3 C9 O4 125.20(15) . . ?
O3 C9 C8 124.00(14) . . ?
O4 C9 C8 110.80(13) . . ?
O5 C10 C8 110.32(14) . . ?
O5 C10 H10B 109.6 . . ?
C8 C10 H10B 109.6 . . ?
O5 C10 H10A 109.6 . . ?
C8 C10 H10A 109.6 . . ?
H10B C10 H10A 108.1 . . ?
C8 C11 H11C 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11C C11 H11B 109.5 . . ?
C8 C11 H11A 109.5 . . ?
H11C C11 H11A 109.5 . . ?
H11B C11 H11A 109.5 . . ?
C8 N1 S1 125.20(11) . . ?
C8 N1 H1 115.8(14) . . ?
S1 N1 H1 114.7(14) . . ?
C9 O4 H4 112.0(13) . . ?
C10 O5 H5 108.5(15) . . ?
O2 S1 O1 118.16(7) . . ?
O2 S1 N1 108.75(7) . . ?
O1 S1 N1 106.43(7) . . ?
O2 S1 C1 106.89(8) . . ?
O1 S1 C1 107.02(7) . . ?
N1 S1 C1 109.40(7) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.394(2) . ?
C1 C6 1.396(2) . ?
C1 S1 1.7806(16) . ?
C2 C3 1.392(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.405(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.390(3) . ?
C4 C7 1.515(3) . ?
C5 C6 1.385(3) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 H7C 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7A 0.9800 . ?
C8 N1 1.490(2) . ?
C8 C11 1.540(2) . ?
C8 C9 1.541(2) . ?
C8 C10 1.544(2) . ?
C9 O3 1.211(2) . ?
C9 O4 1.324(2) . ?
C10 O5 1.420(2) . ?
C10 H10B 0.9900 . ?
C10 H10A 0.9900 . ?
C11 H11C 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11A 0.9800 . ?
N1 S1 1.6165(14) . ?
N1 H1 0.82(2) . ?
O1 S1 1.4462(12) . ?
O2 S1 1.4422(12) . ?
O4 H4 0.98(2) . ?
O5 H5 0.82(2) . ?
