#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/15/7051538.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_7051538
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_absolute_configuration ad
_chemical_formula_moiety         'C14 H16 N2 O7 S'
_chemical_formula_sum            'C14 H16 N2 O7 S'
_chemical_formula_weight         356.35
_chemical_melting_point          411.0(10)
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.764(2)
_cell_length_b                   10.265(3)
_cell_length_c                   19.787(4)
_cell_measurement_reflns_used    14733
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      4.47
_cell_volume                     1577.0(7)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0785
_diffrn_reflns_av_sigmaI/netI    0.0534
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            29265
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         4.47
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         4579
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0410P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0858
_reflns_number_gt                4096
_reflns_number_total             4579
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b513741a.txt
_cod_data_source_block           compound_III
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 '410-412K' was changed to '411.0(10)'
- 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_database_code               7051538
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.97694(6) 0.45399(4) 0.76647(2) 0.01614(10) Uani 1 1 d . . .
O1 O 1.17558(15) 0.48113(11) 0.73871(7) 0.0175(3) Uani 1 1 d . . .
O2 O 0.91795(16) 0.33598(12) 0.73675(7) 0.0196(3) Uani 1 1 d . . .
O3 O 0.89830(16) 0.57602(12) 0.75224(7) 0.0200(3) Uani 1 1 d . . .
O4 O 1.22591(17) 0.31429(13) 0.62921(7) 0.0203(3) Uani 1 1 d . . .
O5 O 1.42003(18) 0.42070(12) 0.83904(7) 0.0212(3) Uani 1 1 d . . .
O6 O 1.59723(16) 0.42770(11) 0.65832(6) 0.0173(3) Uani 1 1 d . . .
O7 O 1.76761(17) 0.31593(12) 0.58486(6) 0.0182(3) Uani 1 1 d . . .
N1 N 1.27521(19) 0.36802(14) 0.74088(8) 0.0152(3) Uani 1 1 d . . .
N2 N 1.5810(2) 0.20832(16) 0.64886(8) 0.0161(3) Uani 1 1 d . . .
H2N H 1.616(3) 0.142(2) 0.6334(11) 0.023(6) Uiso 1 1 d . . .
C1 C 1.3019(2) 0.29773(17) 0.68092(10) 0.0162(4) Uani 1 1 d . . .
C2 C 1.4443(2) 0.19910(17) 0.69784(10) 0.0158(4) Uani 1 1 d . . .
H2 H 1.397(3) 0.113(2) 0.6946(10) 0.019 Uiso 1 1 d . . .
C3 C 1.4964(2) 0.22935(17) 0.77096(10) 0.0164(4) Uani 1 1 d . . .
H3A H 1.458(3) 0.163(2) 0.7991(11) 0.020 Uiso 1 1 d . . .
H3B H 1.612(3) 0.245(2) 0.7760(11) 0.020 Uiso 1 1 d . . .
C4 C 1.4011(2) 0.35088(17) 0.79072(9) 0.0160(4) Uani 1 1 d . . .
C5 C 1.6469(2) 0.32614(18) 0.63293(9) 0.0146(4) Uani 1 1 d . . .
C6 C 1.8466(3) 0.43789(19) 0.56390(10) 0.0193(4) Uani 1 1 d . . .
H6A H 1.920(3) 0.466(2) 0.6010(11) 0.023 Uiso 1 1 d . . .
H6B H 1.756(3) 0.500(2) 0.5565(11) 0.023 Uiso 1 1 d . . .
C7 C 1.9459(3) 0.4089(2) 0.50026(10) 0.0241(4) Uani 1 1 d . . .
H7A H 1.9946 0.4899 0.4823 0.036 Uiso 1 1 calc R . .
H7B H 1.8685 0.3703 0.4667 0.036 Uiso 1 1 calc R . .
H7C H 2.0393 0.3477 0.5104 0.036 Uiso 1 1 calc R . .
C11 C 1.0092(2) 0.43203(17) 0.85303(9) 0.0168(4) Uani 1 1 d . . .
C21 C 1.0280(2) 0.54091(19) 0.89458(9) 0.0183(4) Uani 1 1 d . . .
H21 H 1.013(3) 0.623(2) 0.8759(10) 0.022 Uiso 1 1 d . . .
C31 C 1.0700(3) 0.52182(18) 0.96166(10) 0.0213(4) Uani 1 1 d . . .
H31 H 1.087(3) 0.596(2) 0.9916(11) 0.026 Uiso 1 1 d . . .
C41 C 1.0933(3) 0.39664(19) 0.98775(10) 0.0219(4) Uani 1 1 d . . .
C51 C 1.0714(3) 0.2902(2) 0.94505(11) 0.0244(5) Uani 1 1 d . . .
H51 H 1.078(3) 0.206(2) 0.9633(12) 0.029 Uiso 1 1 d . . .
C61 C 1.0298(3) 0.30620(18) 0.87767(10) 0.0214(4) Uani 1 1 d . . .
H61 H 1.016(3) 0.232(2) 0.8488(11) 0.026 Uiso 1 1 d . . .
C71 C 1.1417(3) 0.3766(2) 1.06090(10) 0.0308(5) Uani 1 1 d . . .
H711 H 1.1428 0.2832 1.0711 0.046 Uiso 1 1 calc R . .
H712 H 1.0574 0.4204 1.0899 0.046 Uiso 1 1 calc R . .
H713 H 1.2564 0.4133 1.0691 0.046 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
O3 S O2 122.02(8) . . ?
O3 S O1 100.69(7) . . ?
O2 S O1 107.77(7) . . ?
O3 S C11 111.69(8) . . ?
O2 S C11 109.99(8) . . ?
O1 S C11 102.31(8) . . ?
N1 O1 S 111.41(10) . . ?
C5 O7 C6 115.48(14) . . ?
O1 N1 C4 120.87(14) . . ?
O1 N1 C1 118.90(15) . . ?
C4 N1 C1 115.34(15) . . ?
C5 N2 C2 119.67(15) . . ?
C5 N2 H2N 123.1(17) . . ?
C2 N2 H2N 117.2(17) . . ?
O4 C1 N1 125.34(17) . . ?
O4 C1 C2 129.54(17) . . ?
N1 C1 C2 105.11(16) . . ?
N2 C2 C3 115.29(15) . . ?
N2 C2 C1 109.90(15) . . ?
C3 C2 C1 105.18(15) . . ?
N2 C2 H2 107.4(13) . . ?
C3 C2 H2 110.5(12) . . ?
C1 C2 H2 108.4(13) . . ?
C4 C3 C2 106.49(15) . . ?
C4 C3 H3A 106.9(13) . . ?
C2 C3 H3A 109.4(13) . . ?
C4 C3 H3B 108.2(13) . . ?
C2 C3 H3B 113.3(14) . . ?
H3A C3 H3B 112(2) . . ?
O5 C4 N1 124.77(17) . . ?
O5 C4 C3 129.85(18) . . ?
N1 C4 C3 105.36(15) . . ?
O6 C5 O7 125.50(16) . . ?
O6 C5 N2 123.32(17) . . ?
O7 C5 N2 111.15(15) . . ?
O7 C6 C7 106.52(15) . . ?
O7 C6 H6A 106.8(13) . . ?
C7 C6 H6A 113.0(14) . . ?
O7 C6 H6B 107.7(14) . . ?
C7 C6 H6B 112.3(13) . . ?
H6A C6 H6B 110.1(18) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C61 C11 C21 121.71(17) . . ?
C61 C11 S 118.73(14) . . ?
C21 C11 S 119.33(13) . . ?
C31 C21 C11 118.53(18) . . ?
C31 C21 H21 122.8(13) . . ?
C11 C21 H21 118.7(13) . . ?
C21 C31 C41 121.10(18) . . ?
C21 C31 H31 120.2(13) . . ?
C41 C31 H31 118.6(13) . . ?
C51 C41 C31 118.81(19) . . ?
C51 C41 C71 120.40(18) . . ?
C31 C41 C71 120.79(18) . . ?
C61 C51 C41 121.44(19) . . ?
C61 C51 H51 119.6(14) . . ?
C41 C51 H51 118.8(14) . . ?
C51 C61 C11 118.40(18) . . ?
C51 C61 H61 120.5(13) . . ?
C11 C61 H61 121.1(13) . . ?
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 O3 1.4217(13) . ?
S O2 1.4223(14) . ?
S O1 1.6607(14) . ?
S C11 1.7455(19) . ?
O1 N1 1.3957(18) . ?
O4 C1 1.193(2) . ?
O5 C4 1.204(2) . ?
O6 C5 1.220(2) . ?
O7 C5 1.339(2) . ?
O7 C6 1.455(2) . ?
N1 C4 1.399(2) . ?
N1 C1 1.404(2) . ?
N2 C5 1.351(2) . ?
N2 C2 1.440(2) . ?
N2 H2N 0.79(2) . ?
C1 C2 1.536(3) . ?
C2 C3 1.534(3) . ?
C2 H2 0.96(2) . ?
C3 C4 1.502(3) . ?
C3 H3A 0.93(2) . ?
C3 H3B 0.92(2) . ?
C6 C7 1.506(3) . ?
C6 H6A 0.97(2) . ?
C6 H6B 0.96(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C11 C61 1.390(3) . ?
C11 C21 1.395(3) . ?
C21 C31 1.381(3) . ?
C21 H21 0.93(2) . ?
C31 C41 1.397(3) . ?
C31 H31 0.98(2) . ?
C41 C51 1.391(3) . ?
C41 C71 1.509(3) . ?
C51 C61 1.382(3) . ?
C51 H51 0.94(2) . ?
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
N2 H2N O5 0.79(2) 2.35(2) 2.962(2) 134(2) 3_846
C2 H2 O3 0.96(2) 2.55(2) 3.106(2) 117.1(15) 3_746
C2 H2 O5 0.96(2) 2.52(2) 3.132(2) 121.5(16) 3_846
C3 H3A O6 0.93(2) 2.59(2) 3.475(2) 158.3(17) 3_846
C71 H712 O6 0.98 2.39 3.345(3) 165.3 2_765
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
O3 S O1 N1 -173.68(11) . . . . ?
O2 S O1 N1 -44.84(13) . . . . ?
C11 S O1 N1 71.09(13) . . . . ?
S O1 N1 C4 -105.01(15) . . . . ?
S O1 N1 C1 100.88(15) . . . . ?
O1 N1 C1 O4 -12.0(3) . . . . ?
C4 N1 C1 O4 -167.53(17) . . . . ?
O1 N1 C1 C2 168.37(13) . . . . ?
C4 N1 C1 C2 12.86(19) . . . . ?
C5 N2 C2 C3 -69.7(2) . . . . ?
C5 N2 C2 C1 48.9(2) . . . . ?
O4 C1 C2 N2 52.7(3) . . . . ?
N1 C1 C2 N2 -127.68(15) . . . . ?
O4 C1 C2 C3 177.42(19) . . . . ?
N1 C1 C2 C3 -2.99(18) . . . . ?
N2 C2 C3 C4 114.70(17) . . . . ?
C1 C2 C3 C4 -6.52(18) . . . . ?
O1 N1 C4 O5 9.4(3) . . . . ?
C1 N1 C4 O5 164.36(17) . . . . ?
O1 N1 C4 C3 -172.12(14) . . . . ?
C1 N1 C4 C3 -17.1(2) . . . . ?
C2 C3 C4 O5 -167.94(19) . . . . ?
C2 C3 C4 N1 13.67(18) . . . . ?
C6 O7 C5 O6 1.9(3) . . . . ?
C6 O7 C5 N2 179.84(15) . . . . ?
C2 N2 C5 O6 0.4(3) . . . . ?
C2 N2 C5 O7 -177.63(15) . . . . ?
C5 O7 C6 C7 -167.53(16) . . . . ?
O3 S C11 C61 158.89(15) . . . . ?
O2 S C11 C61 20.13(18) . . . . ?
O1 S C11 C61 -94.18(16) . . . . ?
O3 S C11 C21 -26.47(18) . . . . ?
O2 S C11 C21 -165.23(14) . . . . ?
O1 S C11 C21 80.46(16) . . . . ?
C61 C11 C21 C31 0.7(3) . . . . ?
S C11 C21 C31 -173.77(15) . . . . ?
C11 C21 C31 C41 0.0(3) . . . . ?
C21 C31 C41 C51 -0.8(3) . . . . ?
C21 C31 C41 C71 179.14(19) . . . . ?
C31 C41 C51 C61 0.9(3) . . . . ?
C71 C41 C51 C61 -179.0(2) . . . . ?
C41 C51 C61 C11 -0.3(3) . . . . ?
C21 C11 C61 C51 -0.5(3) . . . . ?
S C11 C61 C51 173.98(16) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9690735
