#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/56/2005674.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_2005674
loop_
_publ_author_name
'Ellena, J.'
'Punte, G.'
'Nudelman, N. S.'
_publ_section_title
;
 2,4-Dinitrophenyl Phenyl Sulfone
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2929
_journal_page_last               2932
_journal_paper_doi               10.1107/S0108270196008736
_journal_volume                  52
_journal_year                    1996
_chemical_formula_sum            'C12 H8 N2 O6 S'
_chemical_formula_weight         308.26
_chemical_name_systematic
;
2,4-Dinitro-diphenyl-sulfone
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 104.57(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.661(2)
_cell_length_b                   5.478(2)
_cell_length_c                   11.383(3)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17
_cell_measurement_theta_min      8
_cell_volume                     643.4(3)
_computing_cell_refinement       CAD-4
_computing_data_collection       'CAD-4  (Enraf-Nonius, 1993)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics
'PLUTON (Speck ,1990), ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1992)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       CAD-4
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            1341
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.85
_diffrn_standards_decay_%        3
_diffrn_standards_interval_time  100
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_description       prims
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.201
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.06(15)
_refine_ls_extinction_coef       0.026(4)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   1.137
_refine_ls_goodness_of_fit_obs   1.143
_refine_ls_hydrogen_treatment    'refined riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         1270
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.136
_refine_ls_restrained_S_obs      1.143
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_obs          0.0371
_refine_ls_shift/esd_max         0.005
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.03P)²+0.2P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0866
_refine_ls_wR_factor_obs         0.0811
_reflns_number_observed          1127
_reflns_number_total             1270
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            pa1230.cif
_cod_data_source_block           diphenyl-sulfona
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.03P)^2^+0.2P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.03P)^2^+0.2P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2005674
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_type_symbol
S 1 0.13520(9) 0.0710(2) 0.71019(9) 0.0442(3) Uani d . S
O1 1 0.0757(3) -0.0129(7) 0.5898(3) 0.0598(9) Uani d . O
O2 1 0.2075(3) -0.0980(6) 0.7966(3) 0.0617(8) Uani d . O
O11 1 0.4890(3) 0.1959(9) 0.9379(3) 0.0835(12) Uani d . O
O12 1 0.3006(3) 0.2963(8) 0.9599(2) 0.0658(10) Uani d . O
O21 1 0.4378(3) 1.0088(7) 0.5376(3) 0.0802(12) Uani d . O
O22 1 0.5910(4) 0.8977(9) 0.6915(4) 0.0863(12) Uani d . O
N1 1 0.3811(3) 0.2827(7) 0.9023(3) 0.0491(9) Uani d . N
N2 1 0.4841(4) 0.8756(8) 0.6236(4) 0.0594(10) Uani d . N
C1 1 0.2411(3) 0.3128(8) 0.6914(3) 0.0405(9) Uani d . C
C2 1 0.3495(3) 0.3859(8) 0.7803(3) 0.0398(9) Uani d . C
C3 1 0.4321(3) 0.5644(9) 0.7584(3) 0.0446(9) Uani d . C
C4 1 0.4018(4) 0.6718(9) 0.6458(4) 0.0449(10) Uani d . C
C5 1 0.2970(4) 0.6018(11) 0.5550(3) 0.0534(12) Uani d . C
C6 1 0.2178(4) 0.4194(9) 0.5781(3) 0.0468(11) Uani d . C
C7 1 0.0141(4) 0.2058(9) 0.7672(3) 0.0449(10) Uani d . C
C8 1 -0.0218(5) 0.0948(12) 0.8607(4) 0.0723(14) Uani d . C
C9 1 -0.1275(6) 0.1816(17) 0.8974(6) 0.098(2) Uani d . C
C10 1 -0.1927(5) 0.3815(17) 0.8421(6) 0.096(2) Uani d . C
C11 1 -0.1561(5) 0.4936(15) 0.7500(5) 0.088(2) Uani d . C
C12 1 -0.0524(4) 0.4073(11) 0.7112(4) 0.0642(13) Uani d . C
H3 1 0.5055(3) 0.6099(9) 0.8177(3) 0.045(6) Uiso d R H
H5 1 0.2795(4) 0.6774(11) 0.4794(3) 0.045(6) Uiso d R H
H6 1 0.1481(4) 0.3672(9) 0.5166(3) 0.045(6) Uiso d R H
H8 1 0.0250(5) -0.0391(12) 0.8991(4) 0.071(11) Uiso d R H
H9 1 -0.1539(6) 0.1044(17) 0.9599(6) 0.095(11) Uiso d R H
H10 1 -0.2635(5) 0.4417(17) 0.8672(6) 0.095(11) Uiso d R H
H11 1 -0.2011(5) 0.6306(15) 0.7132(5) 0.095(11) Uiso d R H
H12 1 -0.0276(4) 0.4831(11) 0.6475(4) 0.071(11) Uiso d R 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'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 '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'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 3 -4
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 S O1 . 118.9(2) yes
O2 S C7 . 109.8(2) yes
O1 S C7 . 107.4(2) yes
O2 S C1 . 108.4(2) yes
O1 S C1 . 105.3(2) yes
C7 S C1 . 106.2(2) yes
O22 N2 O21 . 125.2(5) yes
O22 N2 C4 . 118.0(4) yes
O21 N2 C4 . 116.8(4) yes
O12 N1 O11 . 125.9(4) yes
O12 N1 C2 . 117.9(3) yes
O11 N1 C2 . 116.2(3) yes
C6 C1 C2 . 118.7(4) yes
C6 C1 S . 117.0(3) yes
C2 C1 S . 124.1(3) yes
C3 C2 C1 . 121.6(4) yes
C3 C2 N1 . 116.2(3) yes
C1 C2 N1 . 122.1(4) yes
C4 C3 C2 . 117.4(4) yes
C4 C3 H3 . 121.4(3) no
C2 C3 H3 . 121.2(2) no
C3 C4 C5 . 122.7(4) yes
C3 C4 N2 . 118.2(4) yes
C5 C4 N2 . 119.1(4) yes
C4 C5 C6 . 118.8(4) yes
C4 C5 H5 . 120.6(3) no
C6 C5 H5 . 120.6(2) no
C5 C6 C1 . 120.7(4) yes
C5 C6 H6 . 119.5(2) no
C1 C6 H6 . 119.7(2) no
C8 C7 C12 . 120.5(4) yes
C8 C7 S . 118.7(4) yes
C12 C7 S . 120.5(3) yes
C7 C8 C9 . 119.6(6) yes
C7 C8 H8 . 119.7(3) no
C9 C8 H8 . 120.7(4) no
C10 C9 C8 . 119.8(6) yes
C10 C9 H9 . 120.0(4) no
C8 C9 H9 . 120.1(4) no
C11 C10 C9 . 120.5(6) yes
C11 C10 H10 . 119.4(4) no
C9 C10 H10 . 120.1(4) no
C10 C11 C12 . 120.4(7) yes
C10 C11 H11 . 119.8(4) no
C12 C11 H11 . 119.8(4) no
C11 C12 C7 . 119.2(5) yes
C11 C12 H12 . 120.4(4) no
C7 C12 H12 . 120.3(3) no
C6 H6 O1 2_556 140.9(5) yes
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
S O2 . 1.427(3) yes
S O1 . 1.433(3) yes
S C7 . 1.748(4) yes
S C1 . 1.788(4) yes
O21 N2 . 1.221(5) yes
O22 N2 . 1.211(5) yes
O11 N1 . 1.216(4) yes
O12 N1 . 1.206(4) yes
N2 C4 . 1.481(6) yes
N1 C2 . 1.459(5) yes
C1 C6 . 1.380(5) yes
C1 C2 . 1.390(5) yes
C2 C3 . 1.380(6) yes
C3 C4 . 1.373(5) yes
C3 H3 . 0.93 no
C4 C5 . 1.372(6) yes
C5 C6 . 1.375(7) yes
C5 H5 . 0.93 no
C6 H6 . 0.93 yes
C7 C8 . 1.361(6) yes
C7 C12 . 1.378(7) yes
C8 C9 . 1.381(8) yes
C8 H8 . 0.93 no
C9 C10 . 1.364(10) yes
C9 H9 . 0.93 no
C10 C11 . 1.355(9) yes
C10 H10 . 0.93 no
C11 C12 . 1.373(6) yes
C11 H11 . 0.93 no
C12 H12 . 0.93 no
C6 O1 2_556 3.252(4) yes
H6 O1 2_556 2.477(4) yes
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
O2 S C1 C6 147.7(3) no
O1 S C1 C6 19.4(4) no
C7 S C1 C6 -94.4(3) no
O2 S C1 C2 -27.4(4) no
O1 S C1 C2 -155.6(3) no
C7 S C1 C2 90.6(4) no
C6 C1 C2 C3 1.2(6) no
S C1 C2 C3 176.2(3) no
C6 C1 C2 N1 179.9(4) no
S C1 C2 N1 -5.1(5) no
O12 N1 C2 C3 122.1(4) no
O11 N1 C2 C3 -56.0(5) no
O12 N1 C2 C1 -56.7(6) no
O11 N1 C2 C1 125.3(4) no
C1 C2 C3 C4 1.4(6) no
N1 C2 C3 C4 -177.4(4) no
C2 C3 C4 C5 -2.6(6) no
C2 C3 C4 N2 175.8(4) no
O22 N2 C4 C3 18.8(6) no
O21 N2 C4 C3 -161.1(4) no
O22 N2 C4 C5 -162.8(4) no
O21 N2 C4 C5 17.3(6) no
C3 C4 C5 C6 1.1(7) no
N2 C4 C5 C6 -177.2(4) no
C4 C5 C6 C1 1.7(6) no
C2 C1 C6 C5 -2.8(6) no
S C1 C6 C5 -178.1(3) no
O2 S C7 C8 -18.5(4) no
O1 S C7 C8 112.2(4) no
C1 S C7 C8 -135.5(4) no
O2 S C7 C12 167.7(4) no
O1 S C7 C12 -61.7(4) no
C1 S C7 C12 50.7(4) no
C12 C7 C8 C9 1.6(8) no
S C7 C8 C9 -172.3(4) no
C7 C8 C9 C10 -1.8(9) no
C8 C9 C10 C11 1.1(10) no
C9 C10 C11 C12 -0.1(10) no
C10 C11 C12 C7 -0.1(8) no
C8 C7 C12 C11 -0.6(7) no
S C7 C12 C11 173.1(4) no
