#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/28/2012859.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2012859
loop_
_publ_author_name
'Crozet, M. D.'
'Vanelle, P.'
'Giorgi, M.'
'Gellis, A.'
_publ_section_title
;
 2-[2-Methyl-5-nitro-4-(phenylsulfonylmethyl)imidazol-1-yl]ethanol and
 2-methyl-5-nitro-4-phenylsulfonylmethyl-1,3-thiazole
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o496
_journal_page_last               o498
_journal_paper_doi               10.1107/S0108270102011964
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C13 H15 N3 O5 S1'
_chemical_formula_moiety         'C13 H15 N3 O5 S1'
_chemical_formula_structural     'C13 H15 N3 O5 S'
_chemical_formula_sum            'C13 H15 N3 O5 S'
_chemical_formula_weight         325.343
_chemical_name_systematic
;
2-(4-benzenesulfonylmethyl-2-methyl-5-nitro-imidazol-1-yl)-ethanol
;
_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           maXus
_cell_angle_alpha                90.
_cell_angle_beta                 94.427(2)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   12.5976(3)
_cell_length_b                   7.7874(3)
_cell_length_c                   14.8929(5)
_cell_measurement_reflns_used    2911
_cell_measurement_temperature    293
_cell_measurement_theta_max      26.4
_cell_measurement_theta_min      2.4
_cell_volume                     1456.67(8)
_computing_cell_refinement       'KappaCCD Reference'
_computing_data_collection       'KappaCCD Reference Manual (Nonius, 1998)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.917
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       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  0.045
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2911
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         2.4
_diffrn_standards_decay_%        <0.1
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.276
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0462
_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)+(0.0359P)²+0.6408P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1129
_reflns_number_gt                2509
_reflns_number_total             2726
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn1013.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C13 H15 N3 O5 S1'
_cod_database_code               2012859
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_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
S1 0.21423(4) 0.02005(6) 0.10308(3) 0.05482(19) Uani d . 1 . . S
O1 0.14467(15) -0.10385(19) 0.05876(12) 0.0865(6) Uani d . 1 . . O
O2 0.32604(12) -0.0151(2) 0.11349(11) 0.0763(5) Uani d . 1 . . O
O3 0.15023(17) 0.6036(2) 0.28117(17) 0.1074(7) Uani d . 1 . . O
O4 0.06922(12) 0.3935(2) 0.21328(12) 0.0743(5) Uani d . 1 . . O
O5 0.45589(12) 0.80584(17) 0.33634(13) 0.0762(5) Uani d . 1 . . O
H5B 0.4093 0.8795 0.3350 0.114 Uiso calc R 1 . . H
N1 0.32903(10) 0.10909(16) 0.31418(9) 0.0388(3) Uani d . 1 . . N
N2 0.31723(11) 0.38808(16) 0.34262(8) 0.0392(3) Uani d . 1 . . N
N3 0.14515(13) 0.4535(2) 0.25888(11) 0.0540(4) Uani d . 1 . . N
C1 0.19509(13) 0.2181(2) 0.04813(11) 0.0461(4) Uani d . 1 . . C
C2 0.10579(15) 0.2396(3) -0.01101(12) 0.0520(4) Uani d . 1 . . C
H2 0.0578 0.1499 -0.0221 0.062 Uiso calc R 1 . . H
C3 0.08906(17) 0.3957(3) -0.05324(13) 0.0602(5) Uani d . 1 . . C
H3 0.0304 0.4108 -0.0943 0.072 Uiso calc R 1 . . H
C4 0.15864(19) 0.5290(3) -0.03497(15) 0.0656(6) Uani d . 1 . . C
H4 0.1457 0.6349 -0.0626 0.079 Uiso calc R 1 . . H
C5 0.24722(18) 0.5075(3) 0.02373(15) 0.0634(5) Uani d . 1 . . C
H5 0.2936 0.5990 0.0357 0.076 Uiso calc R 1 . . H
C6 0.26790(14) 0.3511(3) 0.06516(12) 0.0527(4) Uani d . 1 . . C
H6 0.3289 0.3349 0.1035 0.063 Uiso calc R 1 . . H
C7 0.16892(14) 0.0505(2) 0.21300(13) 0.0491(4) Uani d . 1 . . C
H7A 0.0972 0.0966 0.2071 0.059 Uiso calc R 1 . . H
H7B 0.1663 -0.0600 0.2429 0.059 Uiso calc R 1 . . H
C8 0.23837(12) 0.1683(2) 0.26970(10) 0.0374(3) Uani d . 1 . . C
C9 0.37456(12) 0.2425(2) 0.35730(10) 0.0377(3) Uani d . 1 . . C
C10 0.22990(12) 0.3413(2) 0.28604(10) 0.0386(3) Uani d . 1 . . C
C11 0.47418(15) 0.2306(2) 0.41651(12) 0.0519(4) Uani d . 1 . . C
H11A 0.5009 0.1152 0.4158 0.078 Uiso calc R 1 . . H
H11B 0.4601 0.2613 0.4769 0.078 Uiso calc R 1 . . H
H11C 0.5262 0.3077 0.3952 0.078 Uiso calc R 1 . . H
C12 0.35328(16) 0.5592(2) 0.37392(12) 0.0510(4) Uani d . 1 . . C
H12A 0.3999 0.5475 0.4285 0.061 Uiso calc R 1 . . H
H12B 0.2922 0.6273 0.3879 0.061 Uiso calc R 1 . . H
C13 0.41195(17) 0.6501(2) 0.30297(14) 0.0555(5) Uani d . 1 . . C
H13A 0.4684 0.5766 0.2843 0.067 Uiso calc R 1 . . H
H13B 0.3632 0.6729 0.2507 0.067 Uiso calc R 1 . . H
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_publ_flag
O1 S1 O2 118.94(10) y
O1 S1 C1 108.70(9) ?
O2 S1 C1 108.49(10) ?
O1 S1 C7 106.50(11) ?
O2 S1 C7 107.86(9) ?
C1 S1 C7 105.56(8) y
C13 O5 H5B 109.5 ?
C9 N1 C8 106.62(13) y
C9 N2 C10 105.50(12) y
C9 N2 C12 124.03(14) ?
C10 N2 C12 130.06(14) ?
O3 N3 O4 122.80(17) ?
O3 N3 C10 119.58(17) ?
O4 N3 C10 117.62(16) ?
C2 C1 C6 121.13(18) ?
C2 C1 S1 118.62(15) ?
C6 C1 S1 120.25(14) ?
C3 C2 C1 119.04(19) ?
C3 C2 H2 120.5 ?
C1 C2 H2 120.5 ?
C4 C3 C2 120.29(19) ?
C4 C3 H3 119.9 ?
C2 C3 H3 119.9 ?
C3 C4 C5 120.6(2) ?
C3 C4 H4 119.7 ?
C5 C4 H4 119.7 ?
C4 C5 C6 120.5(2) ?
C4 C5 H5 119.7 ?
C6 C5 H5 119.7 ?
C5 C6 C1 118.38(18) ?
C5 C6 H6 120.8 ?
C1 C6 H6 120.8 ?
C8 C7 S1 112.71(12) y
C8 C7 H7A 109.0 ?
S1 C7 H7A 109.0 ?
C8 C7 H7B 109.0 ?
S1 C7 H7B 109.0 ?
H7A C7 H7B 107.8 ?
N1 C8 C10 108.71(13) y
N1 C8 C7 120.29(14) ?
C10 C8 C7 130.98(15) ?
N1 C9 N2 111.85(13) y
N1 C9 C11 123.64(15) ?
N2 C9 C11 124.48(15) ?
C8 C10 N2 107.30(13) y
C8 C10 N3 128.49(15) ?
N2 C10 N3 123.98(15) ?
C9 C11 H11A 109.5 ?
C9 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
C9 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
N2 C12 C13 110.99(14) y
N2 C12 H12A 109.4 ?
C13 C12 H12A 109.4 ?
N2 C12 H12B 109.4 ?
C13 C12 H12B 109.4 ?
H12A C12 H12B 108.0 ?
O5 C13 C12 110.91(17) y
O5 C13 H13A 109.5 ?
C12 C13 H13A 109.5 ?
O5 C13 H13B 109.5 ?
C12 C13 H13B 109.5 ?
H13A C13 H13B 108.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O1 . 1.4300(15) y
S1 O2 . 1.4314(15) y
S1 C1 . 1.7537(19) y
S1 C7 . 1.791(2) y
O3 N3 . 1.215(2) ?
O4 N3 . 1.222(2) ?
O5 C13 . 1.408(2) y
O5 H5B . 0.8200 ?
N1 C9 . 1.328(2) y
N1 C8 . 1.3562(19) y
N2 C9 . 1.353(2) y
N2 C10 . 1.382(2) y
N2 C12 . 1.472(2) y
N3 C10 . 1.415(2) ?
C1 C2 . 1.384(2) ?
C1 C6 . 1.394(3) ?
C2 C3 . 1.377(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.373(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.374(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.381(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.486(2) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C10 . 1.374(2) y
C9 C11 . 1.480(2) ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 C13 . 1.511(3) y
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O5 H5B N1 1_565 0.82 2.07 2.8562(19) 162
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17253366
