#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/65/2226564.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_2226564
loop_
_publ_author_name
'Hou, Yan-Jun'
'Chu, Wen-Yi'
'Sui, Jun'
'Sun, Zhi-Zhong'
_publ_section_title
;
 Methyl 4-methylsulfonyl-2-nitrobenzoate
;
_journal_coeditor_code           KJ2147
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1669
_journal_paper_doi               10.1107/S1600536810021914
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C9 H9 N O6 S'
_chemical_formula_moiety         'C9 H9 N O6 S'
_chemical_formula_sum            'C9 H9 N O6 S'
_chemical_formula_weight         259.23
_chemical_name_systematic
;
Methyl 4-methylsulfonyl-2-nitrobenzoate
;
_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                 98.955(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0108(12)
_cell_length_b                   8.7671(11)
_cell_length_c                   14.4761(19)
_cell_measurement_reflns_used    2311
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.95
_cell_measurement_theta_min      2.85
_cell_volume                     1129.7(3)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEX CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9661
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.73
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_T_max  0.9475
_exptl_absorpt_correction_T_min  0.9419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.325
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2783
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0411
_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)+(0.0470P)²+0.3279P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1113
_reflns_number_gt                2042
_reflns_number_total             2783
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            kj2147.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226564
_cod_database_fobs_code          2226564
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_type_symbol
_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
S S1 -0.24972(5) 0.42896(5) 0.03839(4) 0.04280(16) Uani d . 1 . .
O O6 0.42147(14) 0.11875(17) 0.20037(9) 0.0491(4) Uani d . 1 . .
O O5 0.28877(18) -0.09358(17) 0.15947(13) 0.0665(5) Uani d . 1 . .
O O4 0.32570(17) 0.07267(19) -0.01616(11) 0.0608(4) Uani d . 1 . .
O O3 0.12224(18) 0.08499(19) -0.11609(9) 0.0581(4) Uani d . 1 . .
O O2 -0.26056(19) 0.53991(19) 0.10923(12) 0.0694(5) Uani d . 1 . .
O O1 -0.24582(17) 0.48263(19) -0.05419(11) 0.0613(4) Uani d . 1 . .
N N1 0.19276(18) 0.10350(18) -0.03781(11) 0.0399(4) Uani d . 1 . .
C C1 -0.3960(2) 0.2976(3) 0.0338(2) 0.0737(8) Uani d . 1 . .
H H1A -0.4905 0.3496 0.0188 0.111 Uiso calc R 1 . .
H H1B -0.3909 0.2482 0.0934 0.111 Uiso calc R 1 . .
H H1C -0.3872 0.2227 -0.0134 0.111 Uiso calc R 1 . .
C C2 -0.0851(2) 0.3192(2) 0.07342(12) 0.0383(4) Uani d . 1 . .
C C4 0.11351(19) 0.16778(19) 0.03452(11) 0.0333(4) Uani d . 1 . .
C C3 -0.01499(19) 0.2509(2) 0.00566(12) 0.0361(4) Uani d . 1 . .
H H3 -0.0535 0.2607 -0.0575 0.043 Uiso calc R 1 . .
C C5 0.1726(2) 0.1479(2) 0.12854(12) 0.0380(4) Uani d . 1 . .
C C8 0.3013(2) 0.0425(2) 0.16253(13) 0.0417(4) Uani d . 1 . .
C C7 -0.0276(2) 0.3049(3) 0.16756(13) 0.0502(5) Uani d . 1 . .
H H7 -0.0750 0.3526 0.2124 0.060 Uiso calc R 1 . .
C C6 0.1005(2) 0.2193(2) 0.19439(13) 0.0489(5) Uani d . 1 . .
H H6 0.1388 0.2094 0.2576 0.059 Uiso calc R 1 . .
C C9 0.5498(2) 0.0281(3) 0.24167(17) 0.0684(7) Uani d . 1 . .
H H9A 0.5205 -0.0387 0.2882 0.103 Uiso calc R 1 . .
H H9B 0.6285 0.0945 0.2703 0.103 Uiso calc R 1 . .
H H9C 0.5853 -0.0313 0.1939 0.103 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 S1 O2 . . 117.69(11) ?
O1 S1 C1 . . 108.11(12) ?
O2 S1 C1 . . 109.99(13) ?
O1 S1 C2 . . 107.80(9) ?
O2 S1 C2 . . 108.17(9) ?
C1 S1 C2 . . 104.24(10) ?
C8 O6 C9 . . 116.36(18) ?
O4 N1 O3 . . 123.86(17) ?
O4 N1 C4 . . 117.96(15) ?
O3 N1 C4 . . 118.18(15) ?
S1 C1 H1A . . 109.5 ?
S1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
S1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C3 C2 C7 . . 121.07(17) ?
C3 C2 S1 . . 119.07(13) ?
C7 C2 S1 . . 119.85(15) ?
C3 C4 C5 . . 122.57(16) ?
C3 C4 N1 . . 117.78(15) ?
C5 C4 N1 . . 119.60(15) ?
C4 C3 C2 . . 117.99(15) ?
C4 C3 H3 . . 121.0 ?
C2 C3 H3 . . 121.0 ?
C6 C5 C4 . . 117.83(16) ?
C6 C5 C8 . . 118.24(16) ?
C4 C5 C8 . . 123.69(17) ?
O5 C8 O6 . . 125.95(18) ?
O5 C8 C5 . . 122.42(17) ?
O6 C8 C5 . . 111.49(17) ?
C6 C7 C2 . . 119.59(18) ?
C6 C7 H7 . . 120.2 ?
C2 C7 H7 . . 120.2 ?
C7 C6 C5 . . 120.91(17) ?
C7 C6 H6 . . 119.5 ?
C5 C6 H6 . . 119.5 ?
O6 C9 H9A . . 109.5 ?
O6 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
O6 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
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 . 1.4260(16) ?
S1 O2 . 1.4278(16) ?
S1 C1 . 1.744(2) ?
S1 C2 . 1.7749(18) ?
O6 C8 . 1.317(2) ?
O6 C9 . 1.453(2) ?
O5 C8 . 1.198(2) ?
O4 N1 . 1.220(2) ?
O3 N1 . 1.221(2) ?
N1 C4 . 1.469(2) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C3 . 1.383(3) ?
C2 C7 . 1.386(2) ?
C4 C3 . 1.377(2) ?
C4 C5 . 1.393(2) ?
C3 H3 . 0.9300 ?
C5 C6 . 1.384(3) ?
C5 C8 . 1.504(3) ?
C7 C6 . 1.381(3) ?
C7 H7 . 0.9300 ?
C6 H6 . 0.9300 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
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
C6 H6 O2 2_545 0.93 2.54 3.370(2) 148.2
C6 H6 O3 4_566 0.93 2.59 3.216(2) 125.2
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 S1 C2 C3 . . . . -25.21(18) ?
O2 S1 C2 C3 . . . . -153.45(16) ?
C1 S1 C2 C3 . . . . 89.52(18) ?
O1 S1 C2 C7 . . . . 153.91(17) ?
O2 S1 C2 C7 . . . . 25.7(2) ?
C1 S1 C2 C7 . . . . -91.4(2) ?
O4 N1 C4 C3 . . . . 157.53(17) ?
O3 N1 C4 C3 . . . . -22.0(2) ?
O4 N1 C4 C5 . . . . -20.2(2) ?
O3 N1 C4 C5 . . . . 160.31(17) ?
C5 C4 C3 C2 . . . . 1.4(3) ?
N1 C4 C3 C2 . . . . -176.25(15) ?
C7 C2 C3 C4 . . . . 0.2(3) ?
S1 C2 C3 C4 . . . . 179.26(13) ?
C3 C4 C5 C6 . . . . -2.1(3) ?
N1 C4 C5 C6 . . . . 175.52(17) ?
C3 C4 C5 C8 . . . . 172.23(17) ?
N1 C4 C5 C8 . . . . -10.2(3) ?
C9 O6 C8 O5 . . . . 0.2(3) ?
C9 O6 C8 C5 . . . . 175.83(17) ?
C6 C5 C8 O5 . . . . 103.2(2) ?
C4 C5 C8 O5 . . . . -71.0(3) ?
C6 C5 C8 O6 . . . . -72.6(2) ?
C4 C5 C8 O6 . . . . 113.1(2) ?
C3 C2 C7 C6 . . . . -0.9(3) ?
S1 C2 C7 C6 . . . . 179.96(17) ?
C2 C7 C6 C5 . . . . 0.2(3) ?
C4 C5 C6 C7 . . . . 1.2(3) ?
C8 C5 C6 C7 . . . . -173.4(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13488043
2 PubChem 22621045
