#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/27/2202795.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_2202795
loop_
_publ_author_name
'Nagarajan Vembu'
'Maruthai Nallu'
'Elinor C. Spencer'
'Judith A. K. Howard'
_publ_section_title
;
 Phenyl 3-nitrobenzenesulfonate
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1213
_journal_page_last               o1215
_journal_paper_doi               10.1107/S1600536803015964
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C12 H9 N O5 S'
_chemical_formula_moiety         'C12 H9 N O5 S'
_chemical_formula_sum            'C12 H9 N O5 S'
_chemical_formula_weight         279.26
_chemical_melting_point          364.0(10)
_chemical_name_common            'Phenyl m-nitrobenzenesulfonate'
_chemical_name_systematic
;
Phenyl 3-nitrobenzenesulfonate
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   difmap
_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                   17.458(4)
_cell_length_b                   12.287(3)
_cell_length_c                   5.4891(14)
_cell_measurement_reflns_used    713
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.653
_cell_measurement_theta_min      2.862
_cell_volume                     1177.4(5)
_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      120(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Proteum M'
_diffrn_measurement_method       /w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bede microsource'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_sigmaI/netI    0.0848
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7868
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.86
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.472
_refine_ls_abs_structure_details '(Flack, 1983), 897 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.01(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.913
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2392
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.913
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0432
_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)+(0.0153P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0563
_refine_ls_wR_factor_ref         0.0598
_reflns_number_gt                1838
_reflns_number_total             2392
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob6276.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '363-365' was changed to '364.0(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 '363-365' was changed to '364.0(10)'
- the average value was taken and precision was
estimated.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to
/home/saulius/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_values 1715 2011-07-08 13:25:40Z adriana 

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_database_code               2202795
_cod_database_fobs_code          2202795
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, 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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 0.11247(15) 0.0630(2) 0.7016(6) 0.0182(6) Uani d . 1 . . C
C2 0.11324(17) 0.1622(2) 0.5871(5) 0.0199(7) Uani d . 1 . . C
H2 0.0838(16) 0.217(2) 0.639(5) 0.024 Uiso d . 1 . . H
C3 0.15896(17) 0.1769(2) 0.3843(5) 0.0217(8) Uani d . 1 . . C
H3 0.1607(14) 0.2488(19) 0.299(5) 0.026 Uiso d . 1 . . H
C4 0.20411(15) 0.0918(2) 0.3034(6) 0.0184(6) Uani d . 1 . . C
H4 0.2345(14) 0.099(2) 0.171(5) 0.022 Uiso d . 1 . . H
C5 0.20319(15) -0.0061(2) 0.4260(5) 0.0160(6) Uani d . 1 . . C
C6 0.15734(16) -0.0239(2) 0.6291(5) 0.0159(6) Uani d . 1 . . C
H6 0.1562(13) -0.089(2) 0.724(5) 0.019 Uiso d . 1 . . H
C7 0.37909(15) 0.0097(2) 0.4286(6) 0.0176(6) Uani d . 1 . . C
C8 0.36942(16) 0.0896(2) 0.6005(6) 0.0212(7) Uani d . 1 . . C
H8 0.3416(15) 0.074(2) 0.734(5) 0.025 Uiso d . 1 . . H
C9 0.40583(17) 0.1882(2) 0.5661(6) 0.0231(7) Uani d . 1 . . C
H9 0.4006(15) 0.2436(19) 0.681(6) 0.028 Uiso d . 1 . . H
C10 0.44987(16) 0.2057(2) 0.3633(6) 0.0220(7) Uani d . 1 . . C
H10 0.4720(14) 0.276(2) 0.336(6) 0.026 Uiso d . 1 . . H
C11 0.45943(16) 0.1234(2) 0.1933(6) 0.0234(7) Uani d . 1 . . C
H11 0.4901(15) 0.136(2) 0.061(5) 0.028 Uiso d . 1 . . H
C12 0.42409(16) 0.0234(2) 0.2258(6) 0.0206(7) Uani d . 1 . . C
H12 0.4291(14) -0.031(2) 0.112(5) 0.025 Uiso d . 1 . . H
N1 0.06214(13) 0.0485(2) 0.9160(4) 0.0238(6) Uani d . 1 . . N
O1 0.02181(11) 0.12588(16) 0.9769(4) 0.0314(6) Uani d . 1 . . O
O2 0.06358(11) -0.03936(16) 1.0221(4) 0.0287(5) Uani d . 1 . . O
O3 0.23727(11) -0.21412(14) 0.4141(3) 0.0249(5) Uani d . 1 . . O
O4 0.27614(11) -0.09700(14) 0.0710(3) 0.0251(5) Uani d . 1 . . O
O5 0.34119(11) -0.09175(14) 0.4680(3) 0.0198(5) Uani d . 1 . . O
S1 0.26294(4) -0.11242(5) 0.32360(13) 0.01894(15) Uani d . 1 . . S
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
C2 C1 C6 123.3(3) ?
C2 C1 N1 118.5(3) ?
C6 C1 N1 118.2(2) ?
C1 C2 C3 119.4(3) ?
C1 C2 H2 121.1(18) ?
C3 C2 H2 119.5(18) ?
C2 C3 C4 119.3(3) ?
C2 C3 H3 120.7(15) ?
C4 C3 H3 120.0(15) ?
C5 C4 C3 119.8(3) ?
C5 C4 H4 118.7(17) ?
C3 C4 H4 121.6(17) ?
C4 C5 C6 122.4(3) ?
C4 C5 S1 118.9(2) ?
C6 C5 S1 118.7(2) ?
C1 C6 C5 115.9(3) ?
C1 C6 H6 118.7(15) ?
C5 C6 H6 125.4(16) ?
C8 C7 C12 122.7(3) ?
C8 C7 O5 117.6(3) ?
C12 C7 O5 119.7(3) ?
C7 C8 C9 118.5(3) ?
C7 C8 H8 118.4(17) ?
C9 C8 H8 123.0(17) ?
C10 C9 C8 120.5(3) ?
C10 C9 H9 119.4(17) ?
C8 C9 H9 120.1(17) ?
C9 C10 C11 120.0(3) ?
C9 C10 H10 119.9(18) ?
C11 C10 H10 120.1(18) ?
C12 C11 C10 120.4(3) ?
C12 C11 H11 120.6(17) ?
C10 C11 H11 119.0(17) ?
C7 C12 C11 117.9(3) ?
C7 C12 H12 121.2(17) ?
C11 C12 H12 120.8(17) ?
O2 N1 O1 124.3(3) y
O2 N1 C1 118.1(2) y
O1 N1 C1 117.6(2) y
C7 O5 S1 117.36(16) y
O3 S1 O4 120.78(11) y
O3 S1 O5 103.67(10) y
O4 S1 O5 108.94(11) y
O3 S1 C5 110.74(13) y
O4 S1 C5 107.98(13) y
O5 S1 C5 103.28(11) y
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
C1 C2 . 1.371(4) ?
C1 C6 . 1.382(4) ?
C1 N1 . 1.480(4) y
C2 C3 . 1.382(4) ?
C2 H2 . 0.89(3) ?
C3 C4 . 1.382(4) ?
C3 H3 . 1.00(2) ?
C4 C5 . 1.379(4) ?
C4 H4 . 0.90(3) ?
C5 C6 . 1.390(4) ?
C5 S1 . 1.763(3) y
C6 H6 . 0.96(3) ?
C7 C8 . 1.372(4) ?
C7 C12 . 1.373(4) ?
C7 O5 . 1.427(3) y
C8 C9 . 1.382(4) ?
C8 H8 . 0.90(3) ?
C9 C10 . 1.370(4) ?
C9 H9 . 0.93(3) ?
C10 C11 . 1.386(4) ?
C10 H10 . 0.95(2) ?
C11 C12 . 1.387(4) ?
C11 H11 . 0.91(3) ?
C12 H12 . 0.92(3) ?
N1 O2 . 1.226(3) y
N1 O1 . 1.230(3) y
O3 S1 . 1.4175(18) y
O4 S1 . 1.418(2) y
O5 S1 . 1.600(2) y
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
C2 H2 O1 . 0.89(2) 2.42(3) 2.707(4) 98.8(18) y
C4 H4 O4 . 0.90(2) 2.57(2) 2.932(3) 104.5(17) y
C6 H6 O2 . 0.94(2) 2.39(2) 2.715(4) 100.2(15) y
C6 H6 O3 . 0.94(2) 2.69(2) 2.968(3) 97.7(16) y
C12 H12 O4 . 0.90(3) 2.80(2) 3.095(3) 100.4(18) y
C3 H3 O3 4_554 1.00(2) 2.80(3) 3.426(4) 121.2(17) y
C3 H3 O5 4_554 1.00(2) 2.67(3) 3.647(3) 165(2) y
C9 H9 O2 4_554 0.93(3) 2.87(2) 3.399(4) 117(2) y
C10 H10 O2 4_554 0.94(2) 2.58(2) 3.260(3) 129.6(19) y
C4 H4 O3 4_554 0.90(2) 2.75(2) 3.364(4) 127.0(18) y
C9 H9 O3 4 0.93(3) 2.78(3) 3.366(4) 121.7(19) y
C3 H3 O4 4 1.00(2) 2.65(2) 3.170(3) 112.2(19) y
C6 H6 O4 1_556 0.94(2) 2.84(2) 3.317(3) 112.9(15) y
C10 H10 O1 3_554 0.94(2) 2.48(3) 3.219(4) 135(2) y
C4 H4 Cg2 . 0.90(2) 3.38 3.72 105 y
C12 H12 Cg2 2_654 0.90(3) 3.13 3.71 124 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
C6 C1 C2 C3 2.1(4) ?
N1 C1 C2 C3 -179.0(2) ?
C1 C2 C3 C4 -1.2(4) ?
C2 C3 C4 C5 -0.2(4) ?
C3 C4 C5 C6 0.8(4) ?
C3 C4 C5 S1 -178.5(2) ?
C2 C1 C6 C5 -1.4(4) ?
N1 C1 C6 C5 179.6(2) ?
C4 C5 C6 C1 0.0(4) ?
S1 C5 C6 C1 179.3(2) ?
C12 C7 C8 C9 0.8(4) ?
O5 C7 C8 C9 179.8(2) ?
C7 C8 C9 C10 0.6(5) ?
C8 C9 C10 C11 -1.3(5) ?
C9 C10 C11 C12 0.5(4) ?
C8 C7 C12 C11 -1.5(4) ?
O5 C7 C12 C11 179.5(2) ?
C10 C11 C12 C7 0.8(4) ?
C2 C1 N1 O2 -177.7(3) ?
C6 C1 N1 O2 1.3(4) ?
C2 C1 N1 O1 1.9(4) ?
C6 C1 N1 O1 -179.1(2) ?
C8 C7 O5 S1 100.0(3) ?
C12 C7 O5 S1 -80.9(3) ?
C7 O5 S1 O3 -175.80(19) ?
C7 O5 S1 O4 54.4(2) ?
C7 O5 S1 C5 -60.2(2) y
C4 C5 S1 O3 -160.8(2) ?
C6 C5 S1 O3 19.8(2) ?
C4 C5 S1 O4 -26.5(2) ?
C6 C5 S1 O4 154.1(2) ?
C4 C5 S1 O5 88.8(2) ?
C6 C5 S1 O5 -90.6(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 85911
