#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007224.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_2007224
loop_
_publ_author_name
'Jeyakanthan, J.'
'Velmurugan, D.'
'Panneerselvam, K.'
'Soriano-Garcia, M.'
'Perumal, S.'
'Chandrasekaran, R.'
_publ_section_title
;
 Three Diphenyl Sulfones
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              630
_journal_page_last               633
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C14 H13 N O4 S'
_chemical_formula_sum            'C14 H13 N O4 S'
_chemical_formula_weight         291.31
_chemical_name_systematic
;
 'Crystal structures of three diphenylsulphones'
;
_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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.000(10)
_cell_angle_beta                 117.410(10)
_cell_angle_gamma                90.000(10)
_cell_formula_units_Z            4
_cell_length_a                   11.5980(10)
_cell_length_b                   10.9590(10)
_cell_length_c                   12.1480(10)
_cell_measurement_reflns_used    21
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      15
_cell_volume                     1370.7(2)
_computing_cell_refinement       'Enraf-Nonius CAD-4 system'
_computing_data_collection       'Enraf-Nonius CAD-4 system (Frenz, 1978)'
_computing_data_reduction        'SDP (Frenz, 1978)'
_computing_molecular_graphics    'ORTEP92 (Vickovic, 1994)'
_computing_publication_material  'PARST (Nardelli, 1983)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf Nonius CAD4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.064
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2349
_diffrn_reflns_theta_max         56.66
_diffrn_reflns_theta_min         4.36
_diffrn_standards_decay_%        <3
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.2
_exptl_absorpt_correction_T_max  0.513
_exptl_absorpt_correction_T_min  0.325
_exptl_absorpt_correction_type   'empirical(DIFABS, Walker & Stuart, 1983)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      not_measured
_exptl_crystal_description       Tabular
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.38
_refine_ls_extinction_coef       0.0080(13)
_refine_ls_extinction_method     SHELXL93_(Sheldrick,_1993)
_refine_ls_goodness_of_fit_all   0.613
_refine_ls_goodness_of_fit_obs   0.611
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           fullcycle
_refine_ls_number_parameters     234
_refine_ls_number_reflns         1788
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.613
_refine_ls_restrained_S_obs      0.611
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_obs          0.037
_refine_ls_shift/esd_max         0.010
_refine_ls_shift/esd_mean        0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.1210P)^2^+1.590P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.113
_refine_ls_wR_factor_obs         0.1079
_reflns_number_observed          1660
_reflns_number_total             1788
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    fr1058.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2007224
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_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
S 0.0444(4) 0.0483(4) 0.0513(4) -0.0028(2) 0.0254(3) -0.0023(2)
N 0.0522(12) 0.086(2) 0.0576(14) -0.0184(12) 0.0323(11) -0.0151(12)
O1 0.0400(9) 0.0801(11) 0.0587(10) -0.0035(8) 0.0214(8) -0.0066(8)
O2 0.0774(11) 0.0434(9) 0.0751(11) -0.0016(8) 0.0406(10) 0.0030(8)
O3 0.0632(12) 0.0906(15) 0.0861(14) 0.0023(11) 0.0345(11) -0.0318(11)
O4 0.104(2) 0.109(2) 0.0490(12) -0.0244(13) 0.0345(11) -0.0074(11)
C1 0.0442(12) 0.0425(12) 0.0517(13) -0.0031(9) 0.0265(10) -0.0078(10)
C2 0.0586(14) 0.0435(12) 0.0498(13) -0.0011(10) 0.0267(11) -0.0058(10)
C3 0.081(2) 0.056(2) 0.0611(15) -0.0084(13) 0.0428(14) -0.0047(12)
C4 0.083(2) 0.080(2) 0.083(2) -0.021(2) 0.059(2) -0.014(2)
C5 0.0534(15) 0.079(2) 0.082(2) -0.0106(13) 0.0407(14) -0.016(2)
C6 0.0427(12) 0.0561(14) 0.0615(14) -0.0022(11) 0.0254(11) -0.0101(11)
C7 0.067(2) 0.076(2) 0.0570(15) 0.0217(14) 0.0255(13) 0.0114(13)
C8 0.0493(15) 0.093(2) 0.080(2) 0.0154(14) 0.0224(14) 0.008(2)
C1' 0.0395(11) 0.0492(13) 0.0479(13) -0.0022(10) 0.0222(10) 0.0004(10)
C2' 0.0545(13) 0.0521(14) 0.0454(12) 0.0075(11) 0.0205(10) 0.0056(11)
C3' 0.0548(14) 0.0536(14) 0.0559(14) 0.0031(11) 0.0259(12) -0.0014(11)
C4' 0.0403(11) 0.0645(15) 0.0459(12) -0.0085(10) 0.0243(10) -0.0065(11)
C5' 0.0527(14) 0.069(2) 0.0465(13) -0.0049(12) 0.0237(11) 0.0093(11)
C6' 0.0581(14) 0.0519(14) 0.0513(13) -0.0004(11) 0.0273(11) 0.0083(11)
loop_
_atom_site_label
_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_occupancy
_atom_site_type_symbol
H3 0.081(3) 0.226(3) -0.576(3) 0.081(8) Uiso d 1 H
H4 0.315(3) 0.184(3) -0.478(3) 0.095(8) Uiso d 1 H
H5 0.417(3) 0.074(3) -0.289(3) 0.096(8) Uiso d 1 H
H71 -0.116(3) 0.243(3) -0.451(3) 0.077(8) Uiso d 1 H
H72 -0.160(3) 0.110(3) -0.517(3) 0.088(8) Uiso d 1 H
H73 -0.109(3) 0.228(3) -0.577(3) 0.092(8) Uiso d 1 H
H81 0.311(3) 0.020(3) -0.080(3) 0.104(8) Uiso d 1 H
H82 0.301(3) -0.093(3) -0.160(3) 0.095(8) Uiso d 1 H
H83 0.420(3) -0.015(3) -0.125(3) 0.103(8) Uiso d 1 H
H2' 0.002(3) 0.286(3) -0.207(3) 0.073(8) Uiso d 1 H
H3' 0.060(3) 0.420(3) -0.031(3) 0.075(8) Uiso d 1 H
H5' 0.217(3) 0.113(3) 0.201(3) 0.077(8) Uiso d 1 H
H6' 0.160(3) -0.017(3) 0.022(3) 0.077(8) Uiso d 1 H
S 0.02620(5) 0.03255(5) -0.24034(5) 0.0467(3) Uani d 1 S
N 0.1645(2) 0.3465(2) 0.2057(2) 0.0626(6) Uani d 1 N
O1 -0.10992(14) 0.0590(2) -0.3137(2) 0.0601(5) Uani d 1 O
O2 0.0625(2) -0.09121(14) -0.2005(2) 0.0632(5) Uani d 1 O
O3 0.1170(2) 0.4493(2) 0.1877(2) 0.0799(6) Uani d 1 O
O4 0.2333(2) 0.3031(2) 0.3090(2) 0.0874(7) Uani d 1 O
C1 0.1153(2) 0.0851(2) -0.3186(2) 0.0444(6) Uani d 1 C
C2 0.0530(2) 0.1492(2) -0.4316(2) 0.0499(6) Uani d 1 C
C3 0.1288(3) 0.1830(2) -0.4885(2) 0.0622(7) Uani d 1 C
C4 0.2592(3) 0.1576(3) -0.4361(3) 0.0738(8) Uani d 1 C
C5 0.3192(2) 0.0968(3) -0.3251(3) 0.0676(8) Uani d 1 C
C6 0.2501(2) 0.0575(2) -0.2631(2) 0.0528(6) Uani d 1 C
C7 -0.0895(3) 0.1839(2) -0.4986(2) 0.0676(8) Uani d 1 C
C8 0.3242(3) -0.0124(3) -0.1449(3) 0.0771(8) Uani d 1 C
C1' 0.0795(2) 0.1271(2) -0.1058(2) 0.0447(6) Uani d 1 C
C2' 0.0504(2) 0.2512(2) -0.1216(2) 0.0516(6) Uani d 1 C
C3' 0.0800(2) 0.3237(2) -0.0190(2) 0.0546(6) Uani d 1 C
C4' 0.1375(2) 0.2694(2) 0.0965(2) 0.0485(6) Uani d 1 C
C5' 0.1691(2) 0.1476(2) 0.1145(2) 0.0557(6) Uani d 1 C
C6' 0.1389(2) 0.0746(2) 0.0111(2) 0.0530(6) Uani d 1 C
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O2 S O1 117.81(13) yes
O2 S C1 109.33(12) yes
O1 S C1 110.06(12) yes
O2 S C1' 108.36(12) yes
O1 S C1' 105.53(12) yes
C1 S C1' 104.92(11) yes
O4 N O3 124.2(3) yes
O4 N C4' 117.6(3) yes
O3 N C4' 118.2(3) yes
C2 C1 C6 121.8(2) ?
C2 C1 S 121.0(2) yes
C6 C1 S 117.2(2) yes
C3 C2 C1 117.2(3) ?
C3 C2 C7 116.6(3) yes
C1 C2 C7 126.2(2) yes
C4 C3 C2 121.9(3) ?
C4 C3 H3 120.9(16) ?
C2 C3 H3 117.2(16) ?
C3 C4 C5 120.4(3) ?
C3 C4 H4 121.6(16) ?
C5 C4 H4 117.9(16) ?
C4 C5 C6 121.5(3) ?
C4 C5 H5 119.8(17) ?
C6 C5 H5 118.7(17) ?
C5 C6 C1 117.3(3) ?
C5 C6 C8 117.1(3) yes
C1 C6 C8 125.6(3) yes
C2 C7 H71 113.4(17) ?
C2 C7 H72 116.5(16) ?
H71 C7 H72 102.(2) ?
C2 C7 H73 110.4(17) ?
H71 C7 H73 104.(2) ?
H72 C7 H73 110.(2) ?
C6 C8 H81 111.5(18) ?
C6 C8 H82 108.6(19) ?
H81 C8 H82 112.(3) ?
C6 C8 H83 108.6(17) ?
H81 C8 H83 113.(3) ?
H82 C8 H83 102.(2) ?
C6' C1' C2' 121.4(2) ?
C6' C1' S 119.7(2) yes
C2' C1' S 118.7(2) yes
C3' C2' C1' 119.6(2) ?
C3' C2' H2' 120.3(17) ?
C1' C2' H2' 120.0(17) ?
C4' C3' C2' 118.2(3) ?
C4' C3' H3' 122.1(16) ?
C2' C3' H3' 119.7(16) ?
C3' C4' C5' 123.3(2) ?
C3' C4' N 118.0(3) yes
C5' C4' N 118.7(2) yes
C4' C5' C6' 118.5(2) ?
C4' C5' H5' 120.7(17) ?
C6' C5' H5' 120.8(17) ?
C1' C6' C5' 119.1(3) ?
C1' C6' H6' 120.8(17) ?
C5' C6' H6' 120.1(17) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S O2 1.437(2) yes
S O1 1.441(2) yes
S C1 1.791(2) yes
S C1' 1.788(3) yes
N O4 1.231(3) yes
N O3 1.228(3) yes
N C4' 1.480(4) yes
C1 C2 1.410(4) ?
C1 C6 1.421(4) ?
C2 C3 1.395(4) ?
C2 C7 1.517(4) yes
C3 C4 1.372(5) ?
C4 C5 1.372(5) ?
C5 C6 1.396(4) ?
C6 C8 1.501(5) yes
C1' C6' 1.387(4) ?
C1' C2' 1.393(4) ?
C2' C3' 1.381(4) ?
C3' C4' 1.381(4) ?
C4' C5' 1.375(4) ?
C5' C6' 1.391(4) ?
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
O2 S C1 C2 134.6(2)
O1 S C1 C2 3.7(2)
C1' S C1 C2 -109.4(2)
O2 S C1 C6 -44.4(2)
O1 S C1 C6 -175.2(2)
C1' S C1 C6 71.7(2)
C6 C1 C2 C3 1.1(4)
S C1 C2 C3 -177.8(2)
C6 C1 C2 C7 -179.7(3)
S C1 C2 C7 1.4(4)
C1 C2 C3 C4 -1.3(4)
C7 C2 C3 C4 179.4(3)
C2 C3 C4 C5 0.2(5)
C3 C4 C5 C6 1.0(5)
C4 C5 C6 C1 -1.2(5)
C4 C5 C6 C8 177.6(3)
C2 C1 C6 C5 0.1(4)
S C1 C6 C5 179.0(2)
C2 C1 C6 C8 -178.6(3)
S C1 C6 C8 0.4(4)
O2 S C1' C6' -2.8(2)
O1 S C1' C6' 124.2(2)
C1 S C1' C6' -119.5(2)
O2 S C1' C2' -177.6(2)
O1 S C1' C2' -50.5(2)
C1 S C1' C2' 65.8(2)
C6' C1' C2' C3' -0.6(4)
S C1' C2' C3' 174.0(2)
C1' C2' C3' C4' -0.3(4)
C2' C3' C4' C5' 1.4(4)
C2' C3' C4' N -177.7(2)
O4 N C4' C3' -169.0(2)
O3 N C4' C3' 11.1(3)
O4 N C4' C5' 11.8(4)
O3 N C4' C5' -168.1(2)
C3' C4' C5' C6' -1.6(4)
N C4' C5' C6' 177.6(2)
C2' C1' C6' C5' 0.4(4)
S C1' C6' C5' -174.1(2)
C4' C5' C6' C1' 0.6(4)