#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/31/2203104.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_2203104
loop_
_publ_author_name
'Nagarajan Vembu'
'Maruthai Nallu'
'Semih Durmus'
'Mathew Pazner'
'Jered Garrison'
'Wiley J. Youngs'
_publ_section_title
;
 4-Methylphenyl 3-nitrobenzenesulfonate
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1
_journal_page_last               o3
_journal_paper_doi               10.1107/S1600536803027090
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C13 H11 NO5 S'
_chemical_formula_moiety         'C13 H11 NO5 S'
_chemical_formula_sum            'C13 H11 N O5 S'
_chemical_formula_weight         293.29
_chemical_melting_point          394.0(10)
_chemical_name_common            'p-methylphenyl 3-nitrobenzenesulfonate'
_chemical_name_systematic
;
 4-Methylphenyl 3-nitrobenzenesulfonate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.267(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2127(13)
_cell_length_b                   12.9944(19)
_cell_length_c                   10.5892(15)
_cell_measurement_reflns_used    6112
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.48
_cell_volume                     1265.6(3)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.905
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7309
_diffrn_reflns_theta_full        28.37
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         2.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_T_max  0.9369
_exptl_absorpt_correction_T_min  0.8956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.271
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         2864
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0332
_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)+(0.0489P)²+0.5196P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0911
_reflns_number_gt                2611
_reflns_number_total             2864
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om6198.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '393-395' was changed to '394.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '393-395' was changed to '394.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2203104
_cod_database_fobs_code          2203104
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_occupancy
_atom_site_type_symbol
S1 0.06680(3) 0.93041(3) 0.30458(3) 0.01784(11) Uani d 1 S
O1 0.41790(11) 1.02520(8) 0.69085(9) 0.0248(2) Uani d 1 O
O2 0.58241(12) 0.90676(9) 0.71275(10) 0.0291(3) Uani d 1 O
O3 0.04280(11) 0.87660(8) 0.18808(9) 0.0233(2) Uani d 1 O
O4 0.07248(11) 1.03981(8) 0.30668(9) 0.0231(2) Uani d 1 O
O5 -0.06041(10) 0.90461(7) 0.39520(9) 0.0204(2) Uani d 1 O
N 0.47364(13) 0.94429(9) 0.65927(11) 0.0205(3) Uani d 1 N
C1 0.22184(14) 0.87864(10) 0.38559(12) 0.0174(3) Uani d 1 C
C2 0.28348(15) 0.93167(10) 0.48895(12) 0.0179(3) Uani d 1 C
C3 0.40617(14) 0.88908(10) 0.54934(12) 0.0178(3) Uani d 1 C
C4 0.46872(15) 0.79852(11) 0.51013(13) 0.0207(3) Uani d 1 C
C5 0.40270(16) 0.74664(11) 0.40794(14) 0.0223(3) Uani d 1 C
C6 0.27922(15) 0.78605(11) 0.34485(13) 0.0201(3) Uani d 1 C
C7 -0.10320(14) 0.80050(11) 0.41111(13) 0.0192(3) Uani d 1 C
C8 -0.05293(16) 0.74991(12) 0.51959(13) 0.0228(3) Uani d 1 C
C9 -0.10083(16) 0.65048(12) 0.53991(14) 0.0235(3) Uani d 1 C
C10 -0.19800(15) 0.60201(11) 0.45383(13) 0.0209(3) Uani d 1 C
C11 -0.24677(15) 0.65614(11) 0.34562(13) 0.0213(3) Uani d 1 C
C12 -0.19974(14) 0.75554(11) 0.32324(13) 0.0207(3) Uani d 1 C
C13 -0.25024(18) 0.49443(12) 0.47685(16) 0.0272(3) Uani d 1 C
H2 0.2415(18) 0.9932(14) 0.5188(16) 0.023(4) Uiso d 1 H
H4 0.553(2) 0.7755(14) 0.5540(17) 0.031(5) Uiso d 1 H
H5 0.444(2) 0.6825(15) 0.3824(18) 0.035(5) Uiso d 1 H
H6 0.2358(19) 0.7536(13) 0.2753(16) 0.026(4) Uiso d 1 H
H8 0.013(2) 0.7845(13) 0.5808(17) 0.027(4) Uiso d 1 H
H9 -0.068(2) 0.6167(15) 0.6142(18) 0.034(5) Uiso d 1 H
H11 -0.316(2) 0.6252(14) 0.2858(17) 0.030(5) Uiso d 1 H
H12 -0.2315(19) 0.7916(14) 0.2512(17) 0.026(4) Uiso d 1 H
H13A -0.241(3) 0.4502(18) 0.405(2) 0.056(7) Uiso d 1 H
H13B -0.210(3) 0.4673(18) 0.554(2) 0.055(6) Uiso d 1 H
H13C -0.353(3) 0.4910(17) 0.477(2) 0.052(6) Uiso d 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
O4 S1 O3 120.52(6) y
O4 S1 O5 103.23(6) y
O3 S1 O5 109.60(6) y
O4 S1 C1 110.29(6) y
O3 S1 C1 108.45(6) y
O5 S1 C1 103.35(6) y
C7 O5 S1 119.37(8) y
O2 N O1 124.10(12) y
O2 N C3 117.95(12) y
O1 N C3 117.96(11) y
C2 C1 C6 121.87(13) ?
C2 C1 S1 118.67(10) ?
C6 C1 S1 119.46(11) ?
C3 C2 C1 116.96(12) ?
C3 C2 H2 121.4(10) ?
C1 C2 H2 121.6(10) ?
C2 C3 C4 123.03(13) ?
C2 C3 N 117.86(12) ?
C4 C3 N 119.11(12) ?
C3 C4 C5 118.43(13) ?
C3 C4 H4 118.2(11) ?
C5 C4 H4 123.4(11) ?
C6 C5 C4 120.59(13) ?
C6 C5 H5 121.0(11) ?
C4 C5 H5 118.5(11) ?
C5 C6 C1 119.09(13) ?
C5 C6 H6 121.6(11) ?
C1 C6 H6 119.2(11) ?
C12 C7 C8 122.16(14) ?
C12 C7 O5 119.69(13) ?
C8 C7 O5 118.01(12) ?
C7 C8 C9 118.58(13) ?
C7 C8 H8 120.1(10) ?
C9 C8 H8 121.3(10) ?
C8 C9 C10 121.26(14) ?
C8 C9 H9 118.5(12) ?
C10 C9 H9 120.2(12) ?
C9 C10 C11 118.32(13) ?
C9 C10 C13 120.99(14) ?
C11 C10 C13 120.70(13) ?
C12 C11 C10 121.34(13) ?
C12 C11 H11 118.6(11) ?
C10 C11 H11 120.0(11) ?
C7 C12 C11 118.34(13) ?
C7 C12 H12 120.1(11) ?
C11 C12 H12 121.5(11) ?
C10 C13 H13A 112.6(14) ?
C10 C13 H13B 112.0(14) ?
H13A C13 H13B 115(2) ?
C10 C13 H13C 111.9(14) ?
H13A C13 H13C 96.0(19) ?
H13B C13 H13C 109(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O3 1.4243(10) y
S1 O4 1.4227(11) y
S1 O5 1.5921(10) y
S1 C1 1.7575(14) y
O1 N 1.2249(16) y
O2 N 1.2239(16) y
O5 C7 1.4218(17) y
N C3 1.4744(17) y
C1 C2 1.3872(19) ?
C1 C6 1.3926(19) ?
C2 C3 1.3822(19) ?
C2 H2 0.950(17) ?
C3 C4 1.3843(19) ?
C4 C5 1.386(2) ?
C4 H4 0.93(2) ?
C5 C6 1.384(2) ?
C5 H5 0.962(19) ?
C6 H6 0.920(18) ?
C7 C12 1.380(2) ?
C7 C8 1.380(2) ?
C8 C9 1.386(2) ?
C8 H8 0.975(18) ?
C9 C10 1.391(2) ?
C9 H9 0.936(19) ?
C10 C11 1.397(2) ?
C10 C13 1.503(2) ?
C11 C12 1.387(2) ?
C11 H11 0.962(19) ?
C12 H12 0.928(18) ?
C13 H13A 0.96(2) ?
C13 H13B 0.95(3) ?
C13 H13C 0.94(2) ?
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
_geom_hbond_publ_flag
C4 H4 O2 . 0.93(2) 2.400(18) 2.7244(19) 100.4(13) y
C2 H2 O1 . 0.950(17) 2.407(17) 2.6981(17) 97.3(12) y
C2 H2 O4 . 0.950(17) 2.727(17) 3.0085(17) 97.9(11) y
C12 H12 O3 . 0.928(18) 2.872(17) 3.1433(17) 98.3(12) y
C6 H6 O3 . 0.920(18) 2.526(17) 2.9107(18) 105.5(12) y
C4 H4 O3 4_676 0.93(2) 2.438(18) 3.0081(17) 119.7(14) y
C2 H2 O5 3_576 0.950(17) 2.356(17) 3.2469(16) 156.0(14) y
C8 H8 O4 3_576 0.975(18) 2.714(17) 3.3047(18) 119.4(13) y
C11 H11 O4 2_445 0.962(19) 2.739(19) 3.6521(18) 158.7(14) y
C13 H13C O3 2_445 0.94(2) 2.83(2) 3.482(2) 127.5(17) y
C13 H13B O2 2_546 0.95(3) 2.79(3) 3.730(2) 174.4(19) y
C9 H9 O1 2_546 0.936(19) 2.695(19) 3.6154(18) 167.9(15) y
C6 H6 O2 4_575 0.920(18) 2.583(18) 3.3515(18) 141.4(14) y
C13 H13A O1 4_575 0.96(2) 2.79(2) 3.4887(19) 130.5(17) y
C5 H5 O4 2_545 0.962(19) 2.727(19) 3.5354(18) 142.0(14) y
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_publ_flag
O4 S1 O5 C7 176.65(10) ?
O3 S1 O5 C7 47.05(11) ?
C1 S1 O5 C7 -68.40(11) y
O4 S1 C1 C2 33.29(12) ?
O3 S1 C1 C2 167.24(10) ?
O5 S1 C1 C2 -76.49(11) ?
O4 S1 C1 C6 -146.80(10) ?
O3 S1 C1 C6 -12.85(13) ?
O5 S1 C1 C6 103.42(11) ?
C6 C1 C2 C3 0.77(19) ?
S1 C1 C2 C3 -179.33(9) ?
C1 C2 C3 C4 0.81(19) ?
C1 C2 C3 N 179.87(11) ?
O2 N C3 C2 -179.90(12) ?
O1 N C3 C2 -0.38(17) ?
O2 N C3 C4 -0.81(18) ?
O1 N C3 C4 178.72(12) ?
C2 C3 C4 C5 -2.0(2) ?
N C3 C4 C5 178.96(12) ?
C3 C4 C5 C6 1.6(2) ?
C4 C5 C6 C1 -0.1(2) ?
C2 C1 C6 C5 -1.1(2) ?
S1 C1 C6 C5 178.98(10) ?
S1 O5 C7 C12 -83.03(14) ?
S1 O5 C7 C8 101.09(13) ?
C12 C7 C8 C9 0.4(2) ?
O5 C7 C8 C9 176.16(11) ?
C7 C8 C9 C10 -0.3(2) ?
C8 C9 C10 C11 -0.1(2) ?
C8 C9 C10 C13 -179.61(13) ?
C9 C10 C11 C12 0.3(2) ?
C13 C10 C11 C12 179.87(13) ?
C8 C7 C12 C11 -0.1(2) ?
O5 C7 C12 C11 -175.84(11) ?
C10 C11 C12 C7 -0.2(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 265684
