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###        Electronic paper (Acta Crystallographica Section E)             ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_journal_date_recd_electronic     2007-04-25
_journal_date_accepted     2007-06-06
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      7
_journal_page_first     o3320
_journal_page_last     o3320
_journal_paper_category     QO
_journal_coeditor_code     SG2167
_publ_contact_author_name
;
Qing-An Wu
;
_publ_contact_author_address
;
State Key Laboratory Breeding Base of Green Chemistry--Synthesis Technology
College of Chemical Engineering and Materials Science
Zhejiang University of Technology
Hangzhou, 310032
People's Republic of China
;
_publ_contact_author_email     wuqa@zj.com
_publ_section_title
;
1-Methyl-4-methylsulfonyl-2-nitrobenzene
;
loop_
    _publ_author_name
    _publ_author_address
    'Qing-An Wu'
;
State Key Laboratory Breeding Base of Green Chemistry--Synthesis Technology
College of Chemical Engineering and Materials Science
Zhejiang University of Technology
Hangzhou 310032
People's Republic of China
;
    'Wei-Ming Fang'
;
State Key Laboratory Breeding Base of Green Chemistry--Synthesis Technology
College of Chemical Engineering and Materials Science
Zhejiang University of Technology
Hangzhou 310032
People's Republic of China
;
    'Da-Wei Luo'
;
State Key Laboratory Breeding Base of Green Chemistry--Synthesis Technology
College of Chemical Engineering and Materials Science
Zhejiang University of Technology
Hangzhou 310032
People's Republic of China
;
    'Zhen-Yuan Xu'
;
State Key Laboratory Breeding Base of Green Chemistry--Synthesis Technology
College of Chemical Engineering and Materials Science
Zhejiang University of Technology
Hangzhou 310032
People's Republic of China
;
data_I
_chemical_name_systematic
;
1-Methyl-4-methylsulfonyl-2-nitrobenzene
;
_chemical_formula_moiety     'C8 H9 N O4 S'
_chemical_formula_sum     'C8 H9 N O4 S'
_chemical_formula_iupac     'C8 H9 N O4 S'
_chemical_formula_weight     215.22
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P c a 21'
_symmetry_space_group_name_Hall     'P 2c -2ac'
loop_
    _symmetry_equiv_pos_site_id
    _symmetry_equiv_pos_as_xyz
    1 '+X,+Y,+Z'
    2 '1/2-X,+Y,1/2+Z'
    3 '1/2+X,-Y,+Z'
    4 '-X,-Y,1/2+Z'
_cell_length_a     14.957(11)
_cell_length_b     8.268(5)
_cell_length_c     7.795(5)
_cell_angle_alpha     90.0000
_cell_angle_beta     90.0000
_cell_angle_gamma     90.0000
_cell_volume     964.1(11)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     7747
_cell_measurement_theta_min     3.6
_cell_measurement_theta_max     27.5
_cell_measurement_temperature     298.0(10)
_exptl_crystal_description     'chunk'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.45
_exptl_crystal_size_mid     0.40
_exptl_crystal_size_min     0.35
_exptl_crystal_density_diffrn     1.483
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     448.00
_exptl_absorpt_coefficient_mu     0.323
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(ABSCOR; Higashi, 1995)'
_exptl_absorpt_correction_T_min     0.856
_exptl_absorpt_correction_T_max     0.893
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type     'Rigaku R-AXIS RAPID'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     10.00
_diffrn_reflns_number     8883
_diffrn_reflns_av_R_equivalents     0.039
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     27.48
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -19
_diffrn_reflns_limit_h_max     19
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -9
_diffrn_reflns_limit_l_max     10
_refine_special_details
;
    Refinement using all reflections. The weighted
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total     2109
_reflns_number_gt     1430
_reflns_threshold_expression     F²>2σ(F²)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_R_factor_gt     0.0325
_refine_ls_wR_factor_ref     0.0770
_refine_ls_goodness_of_fit_ref     1.018
_refine_ls_number_reflns     2109
_refine_ls_number_parameters     129
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details     'w = 1/[0.0001Fo² + σ(Fo²)]/(4Fo²)'
_refine_ls_shift/su_max     0.0000
_refine_diff_density_max     0.23
_refine_diff_density_min     -0.31
_refine_ls_extinction_method     'Larson (1970), equation 22'
_refine_ls_extinction_coef     78(10)
_refine_ls_abs_structure_details     'Flack (1983), 927 Friedel pairs'
_refine_ls_abs_structure_Flack     0.002(8)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
    'H' 'H' 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
    'O' 'O' 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
    'N' 'N' 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
    'S' 'S' 0.125 0.123
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
_computing_data_collection     'PROCESS-AUTO (Rigaku, 1998)'
_computing_cell_refinement     'PROCESS-AUTO'
_computing_data_reduction     'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_solution     'SIR97 (Altomare et al.,  1993)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material     'SHELXL97'
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 0.14758(4) 0.09312(6) 0.41547(12) 0.04659(16) Uani d . 1.00 . .
    O O1 0.48784(12) 0.2707(2) 0.4356(3) 0.0711(6) Uani d . 1.00 . .
    O O2 0.48852(12) 0.4559(2) 0.6321(2) 0.0735(7) Uani d . 1.00 . .
    O O3 0.07388(12) 0.1408(2) 0.3105(2) 0.0659(6) Uani d . 1.00 . .
    O O4 0.20666(12) -0.02992(19) 0.3535(2) 0.0663(6) Uani d . 1.00 . .
    N N1 0.45069(14) 0.3727(2) 0.5241(3) 0.0530(7) Uani d . 1.00 . .
    C C1 0.21356(14) 0.2679(2) 0.4542(3) 0.0403(6) Uani d . 1.00 . .
    C C2 0.30390(16) 0.2549(2) 0.4770(2) 0.0419(7) Uani d . 1.00 . .
    C C3 0.35365(14) 0.3938(2) 0.5021(2) 0.0424(6) Uani d . 1.00 . .
    C C4 0.31618(18) 0.5478(2) 0.5019(3) 0.0504(8) Uani d . 1.00 . .
    C C5 0.2253(2) 0.5549(3) 0.4783(4) 0.0609(9) Uani d . 1.00 . .
    C C6 0.17398(16) 0.4192(3) 0.4536(3) 0.0581(9) Uani d . 1.00 . .
    C C7 0.3700(2) 0.7023(3) 0.5207(4) 0.0733(10) Uani d . 1.00 . .
    C C8 0.1062(2) 0.0349(3) 0.6141(3) 0.0690(10) Uani d . 1.00 . .
    H H2 0.3315 0.1541 0.4756 0.050 Uiso c R 1.00 . .
    H H5 0.1974 0.6554 0.4792 0.073 Uiso c R 1.00 . .
    H H6 0.1127 0.4290 0.4365 0.070 Uiso c R 1.00 . .
    H H71 0.3851 0.7181 0.6392 0.088 Uiso c R 1.00 . .
    H H72 0.4238 0.6941 0.4541 0.088 Uiso c R 1.00 . .
    H H73 0.3352 0.7922 0.4808 0.088 Uiso c R 1.00 . .
    H H81 0.0782 0.1258 0.6686 0.083 Uiso c R 1.00 . .
    H H82 0.0631 -0.0500 0.5990 0.083 Uiso c R 1.00 . .
    H H83 0.1545 -0.0034 0.6844 0.083 Uiso c R 1.00 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    S1 0.0413(3) 0.0524(3) 0.0461(3) -0.0051(2) -0.0017(3) -0.0033(4)
    O1 0.0432(10) 0.0778(12) 0.0924(17) 0.0151(9) 0.0107(13) -0.0011(14)
    O2 0.0488(12) 0.0821(16) 0.0896(17) -0.0209(11) -0.0162(12) -0.0064(13)
    O3 0.0552(12) 0.0772(12) 0.0652(13) -0.0104(10) -0.0213(10) 0.0067(11)
    O4 0.0604(13) 0.0469(9) 0.0916(17) -0.0024(9) 0.0119(10) -0.0192(10)
    N1 0.0408(12) 0.0589(15) 0.0592(15) -0.0022(11) 0.0029(11) 0.0176(12)
    C1 0.0359(12) 0.0442(13) 0.0408(16) 0.0015(10) 0.0013(11) 0.0024(11)
    C2 0.0424(15) 0.0401(13) 0.0431(15) 0.0035(10) 0.0045(11) 0.0012(11)
    C3 0.0328(12) 0.0478(14) 0.0464(13) 0.0007(11) 0.0009(11) 0.0023(12)
    C4 0.0518(16) 0.0462(15) 0.0532(16) -0.0002(12) -0.0001(13) 0.0039(12)
    C5 0.0508(16) 0.0472(15) 0.085(2) 0.0113(13) -0.0065(14) -0.0078(14)
    C6 0.0395(14) 0.0574(15) 0.077(2) 0.0077(12) -0.0054(13) -0.0051(15)
    C7 0.070(2) 0.0471(16) 0.103(2) -0.0069(15) -0.0101(19) -0.0022(17)
    C8 0.0611(19) 0.094(2) 0.0516(17) -0.0259(17) 0.0001(15) 0.0019(17)
_geom_special_details
;
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O3 . . 1.428(2) ?
    S1 O4 . . 1.4316(18) ?
    S1 C1 . . 1.776(2) ?
    S1 C8 . . 1.735(2) ?
    O1 N1 . . 1.223(3) ?
    O2 N1 . . 1.226(3) ?
    N1 C3 . . 1.472(3) ?
    C1 C2 . . 1.367(3) ?
    C1 C6 . . 1.384(3) ?
    C2 C3 . . 1.383(3) ?
    C3 C4 . . 1.391(3) ?
    C4 C5 . . 1.373(4) ?
    C4 C7 . . 1.517(3) ?
    C5 C6 . . 1.373(3) ?
    C2 H2 . . 0.930 ?
    C5 H5 . . 0.930 ?
    C6 H6 . . 0.930 ?
    C7 H71 . . 0.960 ?
    C7 H72 . . 0.960 ?
    C7 H73 . . 0.960 ?
    C8 H81 . . 0.960 ?
    C8 H82 . . 0.960 ?
    C8 H83 . . 0.960 ?
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O3 S1 O4 . . . 118.64(13) ?
    O3 S1 C1 . . . 107.56(11) ?
    O3 S1 C8 . . . 108.20(13) ?
    O4 S1 C1 . . . 107.02(10) ?
    O4 S1 C8 . . . 108.91(13) ?
    C1 S1 C8 . . . 105.78(13) ?
    O1 N1 O2 . . . 124.4(2) ?
    O1 N1 C3 . . . 117.7(2) ?
    O2 N1 C3 . . . 117.9(2) ?
    S1 C1 C2 . . . 120.50(17) ?
    S1 C1 C6 . . . 119.82(17) ?
    C2 C1 C6 . . . 119.6(2) ?
    C1 C2 C3 . . . 119.0(2) ?
    N1 C3 C2 . . . 116.7(2) ?
    N1 C3 C4 . . . 120.4(2) ?
    C2 C3 C4 . . . 122.9(2) ?
    C3 C4 C5 . . . 116.0(2) ?
    C3 C4 C7 . . . 123.8(2) ?
    C5 C4 C7 . . . 120.2(2) ?
    C4 C5 C6 . . . 122.5(2) ?
    C1 C6 C5 . . . 119.9(2) ?
    C1 C2 H2 . . . 120.5 ?
    C3 C2 H2 . . . 120.5 ?
    C4 C5 H5 . . . 118.8 ?
    C6 C5 H5 . . . 118.8 ?
    C1 C6 H6 . . . 120.0 ?
    C5 C6 H6 . . . 120.0 ?
    C4 C7 H71 . . . 109.5 ?
    C4 C7 H72 . . . 109.5 ?
    C4 C7 H73 . . . 109.5 ?
    H71 C7 H72 . . . 109.5 ?
    H71 C7 H73 . . . 109.5 ?
    H72 C7 H73 . . . 109.5 ?
    S1 C8 H81 . . . 109.5 ?
    S1 C8 H82 . . . 109.5 ?
    S1 C8 H83 . . . 109.5 ?
    H81 C8 H82 . . . 109.5 ?
    H81 C8 H83 . . . 109.5 ?
    H82 C8 H83 . . . 109.5 ?
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
    O3 S1 C1 C2 . . . . -149.2(2) ?
    O3 S1 C1 C6 . . . . 27.8(2) ?
    O4 S1 C1 C2 . . . . -20.7(2) ?
    O4 S1 C1 C6 . . . . 156.3(2) ?
    C8 S1 C1 C2 . . . . 95.3(2) ?
    C8 S1 C1 C6 . . . . -87.7(2) ?
    O1 N1 C3 C2 . . . . 38.9(3) ?
    O1 N1 C3 C4 . . . . -139.2(2) ?
    O2 N1 C3 C2 . . . . -139.7(2) ?
    O2 N1 C3 C4 . . . . 42.2(3) ?
    S1 C1 C2 C3 . . . . 178.19(18) ?
    S1 C1 C6 C5 . . . . -178.0(2) ?
    C2 C1 C6 C5 . . . . -1.0(4) ?
    C6 C1 C2 C3 . . . . 1.2(3) ?
    C1 C2 C3 N1 . . . . -179.4(2) ?
    C1 C2 C3 C4 . . . . -1.4(3) ?
    N1 C3 C4 C5 . . . . 179.2(2) ?
    N1 C3 C4 C7 . . . . 1.0(3) ?
    C2 C3 C4 C5 . . . . 1.3(3) ?
    C2 C3 C4 C7 . . . . -177.0(2) ?
    C3 C4 C5 C6 . . . . -1.0(4) ?
    C7 C4 C5 C6 . . . . 177.3(2) ?
    C4 C5 C6 C1 . . . . 0.9(4) ?
