#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/15/7051537.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_7051537
loop_
_publ_author_name
'Stefanowicz, Piotr'
'Jaremko, Łukasz'
'Jaremko, Mariusz'
'Lis, Tadeusz'
_publ_section_title
;
 Crystal-state studies on p-toluenesulfonates of N-oxyimides---a
 possible structural basis of serine proteases inhibition
;
_journal_issue                   2
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              258
_journal_paper_doi               10.1039/b513741a
_journal_volume                  30
_journal_year                    2006
_chemical_formula_moiety         'C11 H11 N O5 S'
_chemical_formula_sum            'C11 H11 N O5 S'
_chemical_formula_weight         269.27
_chemical_melting_point          416.5(5)
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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                 110.58(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.847(3)
_cell_length_b                   11.791(3)
_cell_length_c                   11.014(3)
_cell_measurement_reflns_used    14458
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      3.46
_cell_volume                     1197.2(6)
_computing_cell_refinement       'CrysAlisRED (Oxford Diffraction, 2003)'
_computing_data_collection       'CrysAlisCCD (Oxford Diffraction, 2003)'
_computing_data_reduction        CrysAlisRED
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia,
1997) and PLATON (Spek, 2003)
;
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Xcalibur PX κ geometry'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17314
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         3.46
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3492
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.077
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0800P)²+0.3570P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1229
_reflns_number_gt                3107
_reflns_number_total             3492
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b513741a.txt
_cod_data_source_block           compound_I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/adriana/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '416-417K' was changed to '416.5(5)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7051537
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.18821(3) 0.68568(3) 0.55018(3) 0.02080(11) Uani 1 1 d . . .
O1 O 0.18009(10) 0.82075(7) 0.58670(8) 0.01978(19) Uani 1 1 d . . .
N1 N 0.18341(11) 0.89420(9) 0.48895(9) 0.0182(2) Uani 1 1 d . . .
O4 O -0.06526(10) 0.90425(9) 0.38936(9) 0.0267(2) Uani 1 1 d . . .
O2 O 0.08061(11) 0.66587(9) 0.42659(11) 0.0301(2) Uani 1 1 d . . .
C1 C 0.05354(13) 0.93947(10) 0.40193(11) 0.0206(2) Uani 1 1 d . . .
O3 O 0.18056(12) 0.63522(9) 0.66511(11) 0.0325(2) Uani 1 1 d . . .
O5 O 0.41660(10) 0.95288(9) 0.60191(10) 0.0293(2) Uani 1 1 d . . .
C2 C 0.09756(15) 1.03741(11) 0.33653(12) 0.0244(2) Uani 1 1 d . . .
H2B H 0.047(2) 1.1001(16) 0.3470(17) 0.029 Uiso 1 1 d . . .
H2A H 0.070(2) 1.0178(16) 0.2504(18) 0.029 Uiso 1 1 d . . .
C3 C 0.26157(16) 1.04982(12) 0.40362(14) 0.0280(3) Uani 1 1 d . . .
H3A H 0.311(2) 1.0335(17) 0.3460(19) 0.034 Uiso 1 1 d . . .
H3B H 0.291(2) 1.1160(18) 0.4410(18) 0.034 Uiso 1 1 d . . .
C4 C 0.30498(13) 0.96435(10) 0.51207(12) 0.0212(2) Uani 1 1 d . . .
C11 C 0.36012(13) 0.66859(10) 0.54130(11) 0.0186(2) Uani 1 1 d . . .
C21 C 0.47855(14) 0.65613(12) 0.65539(12) 0.0239(2) Uani 1 1 d . . .
H21 H 0.469(2) 0.6576(16) 0.7380(18) 0.029 Uiso 1 1 d . . .
C31 C 0.61512(14) 0.64317(12) 0.64700(14) 0.0286(3) Uani 1 1 d . . .
H31 H 0.693(2) 0.6232(17) 0.7276(19) 0.034 Uiso 1 1 d . . .
C41 C 0.63344(15) 0.64133(11) 0.52714(15) 0.0276(3) Uani 1 1 d . . .
C51 C 0.51178(16) 0.65002(12) 0.41476(14) 0.0279(3) Uani 1 1 d . . .
H51 H 0.517(2) 0.6448(18) 0.3346(19) 0.033 Uiso 1 1 d . . .
C61 C 0.37443(15) 0.66474(12) 0.42047(12) 0.0244(2) Uani 1 1 d . . .
H61 H 0.289(2) 0.6739(15) 0.3451(19) 0.029 Uiso 1 1 d . . .
C71 C 0.78234(18) 0.62987(15) 0.5189(2) 0.0442(4) Uani 1 1 d . . .
H711 H 0.7777 0.5793 0.4469 0.066 Uiso 1 1 calc R . .
H712 H 0.8491 0.5982 0.6003 0.066 Uiso 1 1 calc R . .
H713 H 0.8171 0.7047 0.5041 0.066 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
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 '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'
C C 0.0033 0.0016 '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
O2 S O3 121.88(7) . . ?
O2 S O1 107.96(6) . . ?
O3 S O1 99.44(6) . . ?
O2 S C11 109.89(7) . . ?
O3 S C11 110.96(7) . . ?
O1 S C11 104.86(5) . . ?
N1 O1 S 113.30(7) . . ?
O1 N1 C4 118.51(10) . . ?
O1 N1 C1 120.03(10) . . ?
C4 N1 C1 114.46(10) . . ?
O4 C1 N1 124.24(12) . . ?
O4 C1 C2 130.00(11) . . ?
N1 C1 C2 105.74(10) . . ?
C1 C2 C3 106.01(10) . . ?
C1 C2 H2B 107.4(12) . . ?
C3 C2 H2B 112.7(12) . . ?
C1 C2 H2A 105.8(12) . . ?
C3 C2 H2A 113.6(12) . . ?
H2B C2 H2A 110.8(16) . . ?
C4 C3 C2 106.06(11) . . ?
C4 C3 H3A 109.0(12) . . ?
C2 C3 H3A 111.4(12) . . ?
C4 C3 H3B 105.5(13) . . ?
C2 C3 H3B 115.4(13) . . ?
H3A C3 H3B 109.2(18) . . ?
O5 C4 N1 124.00(12) . . ?
O5 C4 C3 130.67(12) . . ?
N1 C4 C3 105.32(11) . . ?
C61 C11 C21 121.85(12) . . ?
C61 C11 S 119.09(10) . . ?
C21 C11 S 119.04(10) . . ?
C31 C21 C11 118.46(12) . . ?
C31 C21 H21 119.4(11) . . ?
C11 C21 H21 122.1(11) . . ?
C21 C31 C41 121.03(12) . . ?
C21 C31 H31 116.0(11) . . ?
C41 C31 H31 122.2(11) . . ?
C51 C41 C31 118.91(12) . . ?
C51 C41 C71 120.35(15) . . ?
C31 C41 C71 120.73(15) . . ?
C61 C51 C41 121.18(13) . . ?
C61 C51 H51 116.1(12) . . ?
C41 C51 H51 122.7(12) . . ?
C11 C61 C51 118.50(12) . . ?
C11 C61 H61 118.4(12) . . ?
C51 C61 H61 123.0(12) . . ?
C41 C71 H711 109.5 . . ?
C41 C71 H712 109.5 . . ?
H711 C71 H712 109.5 . . ?
C41 C71 H713 109.5 . . ?
H711 C71 H713 109.5 . . ?
H712 C71 H713 109.5 . . ?
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
S O2 1.4202(12) . ?
S O3 1.4245(11) . ?
S O1 1.6515(10) . ?
S C11 1.7422(13) . ?
O1 N1 1.3910(13) . ?
N1 C4 1.4034(16) . ?
N1 C1 1.4066(16) . ?
O4 C1 1.2032(16) . ?
C1 C2 1.5035(19) . ?
O5 C4 1.2008(16) . ?
C2 C3 1.530(2) . ?
C2 H2B 0.919(19) . ?
C2 H2A 0.920(18) . ?
C3 C4 1.5053(18) . ?
C3 H3A 0.95(2) . ?
C3 H3B 0.88(2) . ?
C11 C61 1.3874(16) . ?
C11 C21 1.3898(17) . ?
C21 C31 1.3893(19) . ?
C21 H21 0.947(19) . ?
C31 C41 1.394(2) . ?
C31 H31 0.98(2) . ?
C41 C51 1.391(2) . ?
C41 C71 1.507(2) . ?
C51 C61 1.388(2) . ?
C51 H51 0.902(19) . ?
C61 H61 0.96(2) . ?
C71 H711 0.9800 . ?
C71 H712 0.9800 . ?
C71 H713 0.9800 . ?
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
C2 H2A O3 0.920(18) 2.458(19) 3.0761(17) 124.7(15) 4_575
C3 H3A O5 0.95(2) 2.54(2) 3.193(2) 126.1(15) 3_676
C31 H31 O4 0.98(2) 2.44(2) 3.383(2) 161.6(16) 4_676
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 S O1 N1 -51.10(9) . . . . ?
O3 S O1 N1 -179.18(8) . . . . ?
C11 S O1 N1 66.03(9) . . . . ?
S O1 N1 C4 -112.77(10) . . . . ?
S O1 N1 C1 98.12(11) . . . . ?
O1 N1 C1 O4 -14.21(18) . . . . ?
C4 N1 C1 O4 -164.49(11) . . . . ?
O1 N1 C1 C2 164.37(9) . . . . ?
C4 N1 C1 C2 14.09(13) . . . . ?
O4 C1 C2 C3 173.24(13) . . . . ?
N1 C1 C2 C3 -5.23(13) . . . . ?
C1 C2 C3 C4 -4.15(14) . . . . ?
O1 N1 C4 O5 12.59(18) . . . . ?
C1 N1 C4 O5 163.35(12) . . . . ?
O1 N1 C4 C3 -167.49(10) . . . . ?
C1 N1 C4 C3 -16.72(14) . . . . ?
C2 C3 C4 O5 -168.10(13) . . . . ?
C2 C3 C4 N1 11.98(14) . . . . ?
O2 S C11 C61 14.15(13) . . . . ?
O3 S C11 C61 151.89(11) . . . . ?
O1 S C11 C61 -101.65(11) . . . . ?
O2 S C11 C21 -164.12(10) . . . . ?
O3 S C11 C21 -26.39(12) . . . . ?
O1 S C11 C21 80.08(11) . . . . ?
C61 C11 C21 C31 2.1(2) . . . . ?
S C11 C21 C31 -179.67(10) . . . . ?
C11 C21 C31 C41 -0.7(2) . . . . ?
C21 C31 C41 C51 -1.5(2) . . . . ?
C21 C31 C41 C71 178.62(13) . . . . ?
C31 C41 C51 C61 2.5(2) . . . . ?
C71 C41 C51 C61 -177.65(13) . . . . ?
C21 C11 C61 C51 -1.2(2) . . . . ?
S C11 C61 C51 -179.40(10) . . . . ?
C41 C51 C61 C11 -1.2(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7971162
