#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/35/2103575.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_2103575
loop_
_publ_author_name
'Wolf, W. M.'
_publ_section_title
;
 X-ray investigations of sulfur-containing fungicides. II.
 Intramolecular forces governing the conformation of four novel
 α-phenylazo- and α-phenylhydrazono-β-ketosulfones
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              54
_journal_page_last               62
_journal_paper_doi               10.1107/S0108768100013197
_journal_volume                  57
_journal_year                    2001
_chemical_formula_sum            'C26 H20 N2 O3 S'
_chemical_formula_weight         440.50
_chemical_name_systematic
;
 benzoylphenylphenylazophenylsulfonylmethane
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 114.80(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.285(3)
_cell_length_b                   16.577(3)
_cell_length_c                   11.421(2)
_cell_measurement_reflns_used    48
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      13.5
_cell_measurement_theta_min      5
_cell_volume                     2283.2(9)
_computing_cell_refinement       'P3 (Siemens, 1989)'
_computing_data_collection       'P3 (Siemens, 1989)'
_computing_data_reduction        'XDISK (Siemens, 1991)'
_computing_molecular_graphics    'InsightII (MSI, 1997), XP (Siemens, 1990)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full .943
_diffrn_measured_fraction_theta_max .943
_diffrn_measurement_device_type  'Siemens P3'
_diffrn_measurement_method       ω--2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71069
_diffrn_reflns_av_R_equivalents  .0329
_diffrn_reflns_av_sigmaI/netI    .0306
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6194
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         2.09
_diffrn_standards_decay_%        5
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .172
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             920
_exptl_crystal_size_max          .45
_exptl_crystal_size_mid          .40
_exptl_crystal_size_min          .25
_refine_diff_density_max         .543
_refine_diff_density_min         -.312
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         5156
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          .0712
_refine_ls_R_factor_gt           .0482
_refine_ls_shift/su_max          .010
_refine_ls_shift/su_mean         .001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0790P)²+0.2414P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1371
_reflns_number_gt                3703
_reflns_number_total             5156
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            os0056.cif
_cod_data_source_block           III
_cod_original_cell_volume        2283.2(8)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2103575
_cod_database_fobs_code          2103575
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
S .77738(4) .02651(3) .74760(5) .04577(15) Uani d 1 S
O1 .69840(15) .08997(9) .71270(17) .0732(5) Uani d 1 O
O2 .89159(12) .04438(10) .82594(15) .0626(4) Uani d 1 O
O3 .57397(11) -.06774(9) .65845(13) .0589(4) Uani d 1 O
N1 .83736(11) -.10215(8) .90155(14) .0389(3) Uani d 1 N
N2 .83359(12) -.15601(9) .82408(14) .0418(3) Uani d 1 N
C1 .74056(14) -.04792(10) .84734(16) .0380(4) Uani d 1 C
C2 .63135(14) -.09179(11) .76617(17) .0404(4) Uani d 1 C
C3 .59637(14) -.16108(11) .82221(17) .0409(4) Uani d 1 C
C4 .50141(17) -.20211(13) .7430(2) .0532(5) Uani d 1 C
H4 .462(2) -.1800(15) .657(2) .070(7) Uiso d 1 H
C5 .4643(2) -.26709(15) .7884(3) .0648(6) Uani d 1 C
H5 .401(3) -.2908(19) .726(3) .101(10) Uiso d 1 H
C6 .5217(2) -.29202(15) .9134(3) .0690(6) Uani d 1 C
H6 .495(2) -.3372(17) .950(3) .086(8) Uiso d 1 H
C7 .6159(2) -.25189(15) .9943(2) .0671(6) Uani d 1 C
H7 .6604(19) -.2673(15) 1.087(2) .067(7) Uiso d 1 H
C8 .65351(17) -.18620(13) .9493(2) .0526(5) Uani d 1 C
H8 .718(2) -.1585(14) 1.004(2) .064(6) Uiso d 1 H
C9 .77133(16) -.01932(12) .60548(18) .0467(4) Uani d 1 C
C10 .6799(2) -.00950(18) .4908(2) .0690(7) Uani d 1 C
H10 .620(2) .0189(15) .488(2) .072(8) Uiso d 1 H
C11 .6824(3) -.0395(3) .3803(3) .0997(11) Uani d 1 C
H11 .624(3) -.026(2) .305(4) .139(14) Uiso d 1 H
C12 .7730(4) -.0784(3) .3838(3) .1096(13) Uani d 1 C
H12 .771(4) -.098(3) .315(4) .156(16) Uiso d 1 H
C13 .8635(3) -.0894(2) .4973(3) .0943(10) Uani d 1 C
H13 .919(3) -.117(2) .499(3) .107(11) Uiso d 1 H
C14 .8642(2) -.05863(16) .6099(2) .0643(6) Uani d 1 C
H14 .933(2) -.0636(14) .692(2) .068(7) Uiso d 1 H
C15 .92878(15) -.20690(11) .86846(18) .0434(4) Uani d 1 C
C16 1.01770(19) -.19859(15) .9866(3) .0684(7) Uani d 1 C
H16 1.018(2) -.1597(17) 1.039(3) .086(9) Uiso d 1 H
C17 1.1068(2) -.24943(19) 1.0194(4) .0961(10) Uani d 1 C
H17 1.168(3) -.244(2) 1.094(4) .128(13) Uiso d 1 H
C18 1.1074(3) -.30818(19) .9368(4) .0951(10) Uani d 1 C
H18 1.169(3) -.342(2) .959(4) .123(12) Uiso d 1 H
C19 1.0196(3) -.3179(2) .8221(3) .0932(10) Uani d 1 C
H19 1.019(3) -.362(2) .769(3) .118(11) Uiso d 1 H
C20 .9297(2) -.26661(16) .7858(2) .0710(7) Uani d 1 C
H20 .868(2) -.2681(16) .689(3) .082(8) Uiso d 1 H
C21 .73181(15) .00269(11) .95375(18) .0420(4) Uani d 1 C
C22 .63161(19) .03687(15) .9363(2) .0625(6) Uani d 1 C
H22 .571(2) .0309(15) .859(2) .073(8) Uiso d 1 H
C23 .6231(2) .08539(17) 1.0294(3) .0758(7) Uani d 1 C
H23 .556(3) .1099(19) 1.010(3) .099(9) Uiso d 1 H
C24 .7141(2) .10074(19) 1.1407(3) .0829(8) Uani d 1 C
H24 .704(2) .1366(18) 1.200(3) .093(9) Uiso d 1 H
C25 .8141(2) .0678(2) 1.1585(3) .0871(9) Uani d 1 C
H25 .882(3) .077(2) 1.244(3) .134(13) Uiso d 1 H
C26 .82340(19) .01890(15) 1.0661(2) .0611(6) Uani d 1 C
H26 .886(2) -.0019(15) 1.077(2) .069(7) 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 .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .1246 .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
O1 S O2 119.12(11) y
O1 S C9 108.54(10) y
O2 S C9 106.95(9) y
O1 S C1 107.90(9) y
O2 S C1 103.54(8) y
C9 S C1 110.63(8) y
N2 N1 C1 111.78(14) y
N1 N2 C15 114.04(15) y
N1 C1 C21 110.25(14) y
N1 C1 C2 113.63(14) y
C21 C1 C2 111.94(14) y
N1 C1 S 104.59(11) y
C21 C1 S 104.41(11) y
C2 C1 S 111.40(12) y
O3 C2 C3 121.08(16) y
O3 C2 C1 119.30(16) y
C3 C2 C1 119.59(15) y
C4 C3 C8 118.96(18) y
C4 C3 C2 117.64(17) y
C8 C3 C2 123.41(17) y
C5 C4 C3 120.8(2) n
C5 C4 H4 123.3(15) n
C3 C4 H4 115.8(15) n
C6 C5 C4 119.9(2) n
C6 C5 H5 126.7(19) n
C4 C5 H5 113.3(19) n
C5 C6 C7 120.4(2) n
C5 C6 H6 121.6(16) n
C7 C6 H6 117.9(16) n
C6 C7 C8 120.0(2) n
C6 C7 H7 123.5(14) n
C8 C7 H7 116.5(14) n
C7 C8 C3 119.9(2) n
C7 C8 H8 120.3(14) n
C3 C8 H8 119.8(14) n
C10 C9 C14 120.8(2) n
C10 C9 S 120.53(18) n
C14 C9 S 118.43(16) n
C11 C10 C9 118.9(3) n
C11 C10 H10 121.1(16) n
C9 C10 H10 120.0(16) n
C12 C11 C10 120.8(3) n
C12 C11 H11 123(3) n
C10 C11 H11 116(3) n
C11 C12 C13 120.8(3) n
C11 C12 H12 118(3) n
C13 C12 H12 121(3) n
C12 C13 C14 119.7(3) n
C12 C13 H13 120(2) n
C14 C13 H13 121(2) n
C9 C14 C13 119.0(2) n
C9 C14 H14 121.2(14) n
C13 C14 H14 119.7(14) n
C20 C15 C16 119.66(19) n
C20 C15 N2 116.45(18) n
C16 C15 N2 123.88(17) n
C17 C16 C15 119.5(2) n
C17 C16 H16 120.4(19) n
C15 C16 H16 120.0(19) n
C18 C17 C16 120.5(3) n
C18 C17 H17 118(2) n
C16 C17 H17 122(2) n
C19 C18 C17 120.3(2) n
C19 C18 H18 120(2) n
C17 C18 H18 120(2) n
C18 C19 C20 120.3(3) n
C18 C19 H19 119(2) n
C20 C19 H19 121(2) n
C15 C20 C19 119.6(2) n
C15 C20 H20 120.5(14) n
C19 C20 H20 119.1(14) n
C26 C21 C22 118.43(19) n
C26 C21 C1 121.30(16) n
C22 C21 C1 120.19(18) n
C23 C22 C21 121.0(2) n
C23 C22 H22 119.3(16) n
C21 C22 H22 119.4(16) n
C24 C23 C22 120.2(2) n
C24 C23 H23 122(2) n
C22 C23 H23 117(2) n
C23 C24 C25 119.3(2) n
C23 C24 H24 116.6(18) n
C25 C24 H24 123.9(18) n
C24 C25 C26 120.9(3) n
C24 C25 H25 120(2) n
C26 C25 H25 119(2) n
C21 C26 C25 120.1(2) n
C21 C26 H26 118.5(16) n
C25 C26 H26 121.3(17) n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S O1 1.4197(16) y
S O2 1.4323(16) y
S C9 1.763(2) y
S C1 1.8780(18) y
O3 C2 1.211(2) y
N1 N2 1.243(2) y
N1 C1 1.476(2) y
N2 C15 1.425(2) y
C1 C21 1.521(2) y
C1 C2 1.538(2) y
C2 C3 1.481(3) y
C3 C4 1.384(3) y
C3 C8 1.390(3) y
C4 C5 1.374(3) y
C5 C6 1.370(4) y
C6 C7 1.375(4) y
C7 C8 1.384(3) y
C9 C10 1.372(3) y
C9 C14 1.377(3) y
C10 C11 1.369(4) y
C11 C12 1.351(5) y
C12 C13 1.361(5) y
C13 C14 1.380(4) y
C15 C20 1.371(3) y
C15 C16 1.378(3) y
C16 C17 1.371(3) y
C17 C18 1.358(4) y
C18 C19 1.349(5) y
C19 C20 1.381(4) y
C21 C26 1.375(3) y
C21 C22 1.382(3) y
C22 C23 1.375(3) y
C23 C24 1.361(4) y
C24 C25 1.371(4) y
C25 C26 1.377(3) y
C4 H4 .97(2) n
C5 H5 .93(3) n
C6 H6 1.00(3) n
C7 H7 1.01(2) n
C8 H8 .94(2) n
C10 H10 .92(3) n
C11 H11 .92(4) n
C12 H12 .83(5) n
C13 H13 .86(3) n
C14 H14 1.00(2) n
C16 H16 .88(3) n
C17 H17 .90(4) n
C18 H18 .93(4) n
C19 H19 .94(4) n
C20 H20 1.07(3) n
C22 H22 .92(2) n
C23 H23 .92(3) n
C24 H24 .95(3) n
C25 H25 1.03(4) n
C26 H26 .86(3) n
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
S C1 C2 O3 -10.7(2) y
S C1 N1 N2 -82.95(15) y
O1 S C1 N1 -168.74(12) y
O1 S C1 C2 68.11(14) y
O1 S C1 C21 -52.89(14) y
O2 S C1 N1 -41.60(13) y
O2 S C1 C2 -164.75(12) y
O2 S C1 C21 74.25(13) y
N1 C1 C2 O3 -128.47(18) y
C1 N1 N2 C15 176.09(14) n
N2 N1 C1 C21 165.33(14) n
N2 N1 C1 C2 38.75(19) n
C9 S C1 N1 72.67(13) n
C9 S C1 C21 -171.48(11) n
C9 S C1 C2 -50.48(14) n
C21 C1 C2 O3 105.84(19) n
