#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:28:26 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201972 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/35/2103574.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_2103574
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            'C20 H15 N3 O5 S'
_chemical_formula_weight         409.41
_chemical_name_systematic
;
 benzoyl(4-nitrophenylhydrazono)phenylsulfonylmethane
;
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.613(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.8351(7)
_cell_length_b                   6.0456(5)
_cell_length_c                   21.0161(12)
_cell_measurement_reflns_used    82
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      9
_cell_volume                     1863.6(2)
_computing_cell_refinement       'KM-4 (Kuma Diffraction, 1991)'
_computing_data_collection       'KM-4 (Kuma Diffraction, 1991)'
_computing_data_reduction        'Dataproc 9.0 (Kuma Diffraction, 1995)'
_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      292(2)
_diffrn_measured_fraction_theta_full .878
_diffrn_measured_fraction_theta_max .878
_diffrn_measurement_device_type  'Kuma Diffraction KM-4'
_diffrn_measurement_method       ω--2θ
_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  .0204
_diffrn_reflns_av_sigmaI/netI    .0240
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4566
_diffrn_reflns_theta_full        74.91
_diffrn_reflns_theta_max         74.91
_diffrn_reflns_theta_min         3.94
_diffrn_standards_decay_%        5
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.892
_exptl_absorpt_correction_T_max  .797
_exptl_absorpt_correction_T_min  .445
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'XEMP (Siemens, 1991)'
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          .42
_exptl_crystal_size_mid          .21
_exptl_crystal_size_min          .12
_exptl_crystal_size_rad          .25
_refine_diff_density_max         .331
_refine_diff_density_min         -.488
_refine_ls_extinction_coef       .0019(3)
_refine_ls_extinction_method     'SHELXL (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   .932
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         3710
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      .932
_refine_ls_R_factor_all          .0611
_refine_ls_R_factor_gt           .0488
_refine_ls_shift/su_max          .007
_refine_ls_shift/su_mean         .001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0759P)²+1.2875P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1459
_reflns_number_gt                2943
_reflns_number_total             3710
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            os0056.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2103574
_cod_database_fobs_code          2103574
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
S .51978(4) .43082(11) .10524(3) .0542(2) Uani d 1 S
O1 .54900(14) .2193(4) .08498(10) .0735(6) Uani d 1 O
O2 .53454(12) .6212(3) .06644(9) .0676(5) Uani d 1 O
O3 .43199(13) .1399(3) .18090(11) .0771(6) Uani d 1 O
O4 .11839(18) 1.4824(4) -.09700(12) .0923(7) Uani d 1 O
O5 .01586(17) 1.2996(5) -.05798(16) .1150(10) Uani d 1 O
N1 .33994(14) .5617(3) .07870(9) .0517(5) Uani d 1 N
N2 .35991(15) .7264(4) .04234(10) .0552(5) Uani d 1 N
H2 .417(2) .749(5) .0365(14) .069(9) Uiso d 1 H
N3 .09448(18) 1.3274(4) -.06644(12) .0730(7) Uani d 1 N
C1 .39941(16) .4259(4) .10873(11) .0509(5) Uani d 1 C
C2 .37056(18) .2459(4) .14986(12) .0556(6) Uani d 1 C
C3 .27397(17) .1880(4) .15439(11) .0530(6) Uani d 1 C
C4 .2594(2) -.0202(5) .17955(13) .0615(6) Uani d 1 C
H4 .310(2) -.110(5) .1917(14) .074(9) Uiso d 1 H
C5 .1733(2) -.0879(6) .18735(15) .0698(8) Uani d 1 C
H5 .166(2) -.230(6) .2067(16) .085(10) Uiso d 1 H
C6 .1000(2) .0499(6) .17052(17) .0788(9) Uani d 1 C
H6 .041(3) .006(6) .1763(17) .098(11) Uiso d 1 H
C7 .1131(2) .2566(7) .14643(19) .0857(10) Uani d 1 C
H7 .062(3) .341(7) .135(2) .116(14) Uiso d 1 H
C8 .1993(2) .3256(5) .13822(15) .0694(8) Uani d 1 C
H8 .204(2) .472(6) .1201(16) .085(10) Uiso d 1 H
C9 .57342(16) .4895(4) .18383(11) .0523(6) Uani d 1 C
C10 .5605(2) .6971(5) .20879(14) .0642(7) Uani d 1 C
H10 .522(2) .807(6) .1847(16) .085(10) Uiso d 1 H
C11 .6027(2) .7464(6) .27005(16) .0764(9) Uani d 1 C
H11 .596(3) .885(6) .2880(18) .097(12) Uiso d 1 H
C12 .6585(2) .5934(7) .30477(15) .0775(9) Uani d 1 C
H12 .688(2) .633(6) .3481(17) .090(10) Uiso d 1 H
C13 .6715(2) .3889(7) .27945(15) .0776(9) Uani d 1 C
H13 .714(3) .284(7) .3027(19) .107(12) Uiso d 1 H
C14 .6282(2) .3330(5) .21858(14) .0646(7) Uani d 1 C
H14 .634(2) .186(6) .1968(16) .089(11) Uiso d 1 H
C15 .29122(16) .8694(4) .01444(10) .0506(5) Uani d 1 C
C16 .20005(18) .8286(5) .01620(13) .0603(6) Uani d 1 C
H16 .183(2) .707(5) .0374(15) .072(9) Uiso d 1 H
C17 .13536(19) .9797(5) -.01041(14) .0642(7) Uani d 1 C
H17 .068(2) .951(5) -.0085(15) .083(10) Uiso d 1 H
C18 .16369(18) 1.1678(5) -.03884(12) .0574(6) Uani d 1 C
C19 .25361(19) 1.2086(5) -.04213(12) .0570(6) Uani d 1 C
H19 .270(2) 1.326(5) -.0622(15) .074(9) Uiso d 1 H
C20 .31822(18) 1.0581(4) -.01534(11) .0547(6) Uani d 1 C
H20 .382(2) 1.086(5) -.0152(14) .070(8) 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 .0181 .0091 '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 .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .3331 .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
O1 S O2 117.64(12) y
O1 S C9 110.13(12) y
O2 S C9 106.46(12) y
O1 S C1 110.08(12) y
O2 S C1 105.73(11) y
C9 S C1 106.11(11) y
C1 N1 N2 124.4(2) y
N1 N2 C15 119.9(2) y
N1 N2 H2 120(2) n
C15 N2 H2 120(2) n
O5 N3 O4 123.0(3) y
O5 N3 C18 118.8(3) y
O4 N3 C18 118.3(3) y
N1 C1 C2 120.7(2) y
N1 C1 S 125.22(19) y
C2 C1 S 114.10(17) y
O3 C2 C3 119.4(2) y
O3 C2 C1 115.9(2) y
C3 C2 C1 124.7(2) y
C8 C3 C4 118.1(3) y
C8 C3 C2 125.7(2) y
C4 C3 C2 116.1(2) y
C5 C4 C3 120.9(3) n
C5 C4 H4 121(2) n
C3 C4 H4 118(2) n
C6 C5 C4 120.2(3) n
C6 C5 H5 121(2) n
C4 C5 H5 119(2) n
C5 C6 C7 119.8(3) n
C5 C6 H6 121(2) n
C7 C6 H6 119(2) n
C6 C7 C8 120.4(3) n
C6 C7 H7 117(3) n
C8 C7 H7 123(3) n
C7 C8 C3 120.6(3) n
C7 C8 H8 117(2) n
C3 C8 H8 123(2) n
C14 C9 C10 121.6(3) n
C14 C9 S 120.3(2) n
C10 C9 S 118.0(2) n
C11 C10 C9 118.8(3) n
C11 C10 H10 119(2) n
C9 C10 H10 122(2) n
C12 C11 C10 120.2(3) n
C12 C11 H11 119(2) n
C10 C11 H11 121(2) n
C13 C12 C11 120.6(3) n
C13 C12 H12 121(2) n
C11 C12 H12 119(2) n
C12 C13 C14 120.4(3) n
C12 C13 H13 121(2) n
C14 C13 H13 119(2) n
C9 C14 C13 118.4(3) n
C9 C14 H14 117(2) n
C13 C14 H14 125(2) n
C16 C15 C20 120.6(2) n
C16 C15 N2 122.3(2) n
C20 C15 N2 117.1(2) n
C17 C16 C15 119.7(3) n
C17 C16 H16 120.1(19) n
C15 C16 H16 120.1(19) n
C18 C17 C16 118.8(3) n
C18 C17 H17 121.5(18) n
C16 C17 H17 119.7(18) n
C19 C18 C17 122.2(2) n
C19 C18 N3 119.5(3) n
C17 C18 N3 118.3(3) n
C18 C19 C20 118.9(3) n
C18 C19 H19 121(2) n
C20 C19 H19 120(2) n
C19 C20 C15 119.8(2) n
C19 C20 H20 120.5(18) n
C15 C20 H20 119.7(18) n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S O1 1.435(2) y
S O2 1.4463(19) y
S C9 1.759(2) y
S C1 1.798(2) y
O3 C2 1.220(3) y
O4 N3 1.219(3) y
O5 N3 1.218(3) y
N1 C1 1.298(3) y
N1 N2 1.315(3) y
N2 C15 1.397(3) y
N3 C18 1.464(3) y
C1 C2 1.492(3) y
C2 C3 1.492(4) y
C3 C8 1.386(4) y
C3 C4 1.394(4) y
C4 C5 1.374(4) y
C5 C6 1.373(5) y
C6 C7 1.373(5) y
C7 C8 1.380(4) y
C9 C14 1.383(4) y
C9 C10 1.384(4) y
C10 C11 1.377(4) y
C11 C12 1.375(5) y
C12 C13 1.371(5) y
C13 C14 1.385(4) y
C15 C16 1.381(4) y
C15 C20 1.388(3) y
C16 C17 1.381(4) y
C17 C18 1.379(4) y
C18 C19 1.368(4) y
C19 C20 1.379(4) y
N2 H2 .89(3) n
C4 H4 .93(3) n
C5 H5 .96(4) n
C6 H6 .95(4) n
C7 H7 .92(4) n
C8 H8 .97(4) n
C10 H10 .97(3) n
C11 H11 .93(4) n
C12 H12 .98(4) n
C13 H13 .97(4) n
C14 H14 1.01(4) n
C16 H16 .91(3) n
C17 H17 1.03(3) n
C19 H19 .88(3) n
C20 H20 .97(3) n
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2 O2 .89(3) 1.91(3) 2.642(3) 139(3)
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 7.2(3) y
S C1 N1 N2 -1.6(3) y
O1 S C1 N1 -124.5(2) y
O1 S C1 C2 54.9(2) y
O2 S C1 N1 3.5(2) y
O2 S C1 C2 -177.04(17) y
N1 C1 C2 O3 -173.3(2) y
C9 S C1 N1 116.3(2) n
C9 S C1 C2 -64.2(2) n
C1 N1 N2 C15 -177.1(2) n
N2 N1 C1 C2 179.0(2) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8820538
