#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/22/2012215.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_2012215
loop_
_publ_author_name
'Wolf, Wojciech M.'
_publ_section_title
;
 X-ray investigations of sulfur-containing fungicides. IV.
 4'-{[Benzoyl(4-chlorophenylhydrazono)methyl]sulfonyl}acetanilide and
 4'-{[benzoyl(4-methoxyphenylhydrazono)methyl]sulfonyl}acetanilide
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1112
_journal_page_last               1115
_journal_paper_doi               10.1107/S0108270101010642
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C23 H21 N3 O5 S'
_chemical_formula_sum            'C23 H21 N3 O5 S'
_chemical_formula_weight         451.49
_chemical_name_systematic
;
4'-{[benzoyl(4-methoxyphenylhydrazono)methyl]sulfonyl}acetanilide
;
_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           'manual editing of the SHELXL97 .cif file'
_cell_angle_alpha                90
_cell_angle_beta                 91.53(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4897(12)
_cell_length_b                   7.4158(9)
_cell_length_c                   25.507(3)
_cell_measurement_reflns_used    48
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      10.2
_cell_measurement_theta_min      4.5
_cell_volume                     2172.6(4)
_computing_cell_refinement       P3
_computing_data_collection       'P3 (Siemens, 1989)'
_computing_data_reduction        'XDISK (Siemens, 1991)'
_computing_molecular_graphics
'InsightII (Molecular Simulations, 1997) and XP (Siemens, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  SHELXL97
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .920
_diffrn_measured_fraction_theta_max .920
_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     .71073
_diffrn_reflns_av_R_equivalents  .052
_diffrn_reflns_av_sigmaI/netI    .040
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            5473
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         1.93
_diffrn_standards_decay_%        18
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .190
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          .55
_exptl_crystal_size_mid          .35
_exptl_crystal_size_min          .15
_refine_diff_density_max         .22
_refine_diff_density_min         -.34
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         3823
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          .070
_refine_ls_R_factor_gt           .042
_refine_ls_shift/su_max          .002
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0674P)²+0.2858P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .127
_reflns_number_gt                2647
_reflns_number_total             3823
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jz1471.cif
_cod_data_source_block           II
_cod_original_cell_volume        2172.5(4)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2012215
_cod_database_fobs_code          2012215
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
S .61621(5) .59505(10) .17476(2) .0521(2) Uani d . 1 . . S
O1 .60399(17) .7844(3) .16310(7) .0666(6) Uani d . 1 . . O
O2 .70669(15) .5408(3) .21149(7) .0706(6) Uani d . 1 . . O
O3 .38431(15) .5667(3) .12279(6) .0559(5) Uani d . 1 . . O
O4 .6503(2) -.0913(3) -.00458(8) .0757(6) Uani d . 1 . . O
O5 .46487(18) .2345(3) .48744(7) .0756(6) Uani d . 1 . . O
N1 .47501(15) .4549(3) .25010(7) .0398(5) Uani d . 1 . . N
N2 .55876(17) .4410(3) .28465(7) .0453(5) Uani d . 1 . . N
H2 .630(3) .465(4) .2764(11) .070(9) Uiso d . 1 . . H
N3 .63852(18) .2040(3) -.02660(8) .0483(5) Uani d . 1 . . N
H3 .628(2) .276(4) -.0542(11) .053(7) Uiso d . 1 . . H
C1 .48435(19) .5148(3) .20211(9) .0429(6) Uani d . 1 . . C
C2 .37866(19) .5247(3) .16923(8) .0411(5) Uani d . 1 . . C
C3 .26206(19) .4801(3) .19102(8) .0392(5) Uani d . 1 . . C
C4 .2266(2) .5384(3) .23990(9) .0440(6) Uani d . 1 . . C
H4 .2798(15) .5993(18) .2628(7) .057(3) Uiso calc R 1 . . H
C5 .1139(2) .5073(4) .25510(10) .0524(7) Uani d . 1 . . C
H5 .0898(7) .5480(13) .2885(10) .057(3) Uiso calc R 1 . . H
C6 .0364(2) .4183(4) .22238(11) .0578(7) Uani d . 1 . . C
H6 -.040(2) .3982(7) .2329(3) .057(3) Uiso calc R 1 . . H
C7 .0705(2) .3588(4) .17432(11) .0555(7) Uani d . 1 . . C
H7 .0185(15) .2965(19) .1526(6) .057(3) Uiso calc R 1 . . H
C8 .1824(2) .3916(3) .15829(9) .0473(6) Uani d . 1 . . C
H8 .2044(7) .3543(12) .1255(10) .057(3) Uiso calc R 1 . . H
C9 .6335(2) .4780(4) .11585(9) .0472(6) Uani d . 1 . . C
C10 .6465(2) .2921(4) .11625(11) .0591(7) Uani d . 1 . . C
H10 .6528(3) .229(2) .1488(10) .063(4) Uiso calc R 1 . . H
C11 .6503(2) .1982(4) .06995(10) .0584(7) Uani d . 1 . . C
H11 .6575(3) .079(4) .07039(10) .063(4) Uiso calc R 1 . . H
C12 .64300(19) .2895(3) .02237(9) .0441(6) Uani d . 1 . . C
C13 .6359(2) .4766(3) .02270(10) .0468(6) Uani d . 1 . . C
H13 .6355(2) .538(2) -.0084(10) .063(4) Uiso calc R 1 . . H
C14 .6293(2) .5702(4) .06881(10) .0493(6) Uani d . 1 . . C
H14 .6218(3) .698(4) .06842(10) .063(4) Uiso calc R 1 . . H
C15 .6394(2) .0249(4) -.03769(11) .0525(6) Uani d . 1 . . C
C16 .6277(3) -.0188(4) -.09492(11) .0659(8) Uani d . 1 . . C
H161 .5726(11) .0659(16) -.1120(4) .119(8) Uiso calc R 1 . . H
H162 .5986(6) -.143(2) -.09927(15) .119(8) Uiso calc R 1 . . H
H163 .7044(15) -.0080(5) -.1111(3) .119(8) Uiso calc R 1 . . H
C17 .53525(18) .3858(3) .33639(8) .0391(5) Uani d . 1 . . C
C18 .4251(2) .3332(3) .35020(9) .0458(6) Uani d . 1 . . C
H18 .3646(17) .3325(4) .3256(7) .057(4) Uiso calc R 1 . . H
C19 .4068(2) .2820(4) .40092(9) .0487(6) Uani d . 1 . . C
H19 .334(2) .2445(11) .4101(3) .057(4) Uiso calc R 1 . . H
C20 .4951(2) .2857(4) .43840(9) .0499(6) Uani d . 1 . . C
C21 .6048(2) .3385(4) .42436(10) .0608(7) Uani d . 1 . . C
H21 .6663(17) .3415(4) .4496(7) .057(4) Uiso calc R 1 . . H
C22 .6241(2) .3872(4) .37291(10) .0545(7) Uani d . 1 . . C
H22 .697(2) .4206(11) .3634(3) .057(4) Uiso calc R 1 . . H
C23 .5531(3) .2246(6) .52671(12) .0906(12) Uani d . 1 . . C
H231 .6058(12) .126(2) .5189(2) .118(8) Uiso calc R 1 . . H
H232 .5183(7) .2033(7) .5605(7) .118(8) Uiso calc R 1 . . H
H233 .5962(10) .337(2) .52788(12) .118(8) Uiso calc R 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 118.15(13) y
O1 S C1 109.04(11) y
O1 S C9 108.56(12) y
O2 S C1 104.97(11) y
O2 S C9 108.87(12) y
C1 S C9 106.67(12) y
N2 N1 C1 125.93(19) y
N1 N2 C17 120.15(18) y
N1 C1 C2 117.82(19) y
S C1 N1 124.71(17) y
S C1 C2 117.40(16) y
O3 C2 C1 120.2(2) y
O3 C2 C3 118.9(2) y
C1 C2 C3 120.89(19) y
C15 N3 C12 128.9(2) y
C20 O5 C23 118.1(2) y
C8 C3 C4 118.9(2) n
C8 C3 C2 117.5(2) n
C4 C3 C2 123.3(2) n
C5 C4 C3 119.9(2) n
C6 C5 C4 120.5(2) n
C7 C6 C5 120.2(2) n
C7 C8 C3 120.6(2) n
C6 C7 C8 119.9(3) n
C14 C9 C10 120.0(3) n
C14 C9 S 119.9(2) n
C10 C9 S 120.1(2) n
C11 C10 C9 120.3(3) n
C10 C11 C12 120.1(3) n
C13 C12 C11 118.9(2) n
C13 C12 N3 117.2(2) n
C11 C12 N3 123.9(2) n
C14 C13 C12 121.1(2) n
C13 C14 C9 119.6(2) n
O4 C15 N3 123.5(3) n
O4 C15 C16 122.0(3) n
N3 C15 C16 114.5(2) n
C22 C17 C18 120.2(2) n
C22 C17 N2 118.5(2) n
C18 C17 N2 121.3(2) n
C19 C18 C17 119.0(2) n
C18 C19 C20 121.4(2) n
O5 C20 C19 115.5(2) n
O5 C20 C21 125.2(2) n
C19 C20 C21 119.2(2) n
C20 C21 C22 119.5(2) n
C17 C22 C21 120.7(2) n
N1 N2 H2 120.4(19) n
C17 N2 H2 119.5(19) n
C15 N3 H3 115.3(17) n
C12 N3 H3 115.6(17) n
C5 C4 H4 120.0 n
C3 C4 H4 120.0 n
C6 C5 H5 119.8 n
C4 C5 H5 119.8 n
C7 C6 H6 119.9 n
C5 C6 H6 119.9 n
C6 C7 H7 120.0 n
C8 C7 H7 120.0 n
C7 C8 H8 119.7 n
C3 C8 H8 119.7 n
C11 C10 H10 119.9 n
C9 C10 H10 119.9 n
C10 C11 H11 120.0 n
C12 C11 H11 120.0 n
C14 C13 H13 119.5 n
C12 C13 H13 119.5 n
C13 C14 H14 120.2 n
C9 C14 H14 120.2 n
C15 C16 H161 109.5 n
C15 C16 H162 109.5 n
H161 C16 H162 109.5 n
C15 C16 H163 109.5 n
H161 C16 H163 109.5 n
H162 C16 H163 109.5 n
C19 C18 H18 120.5 n
C17 C18 H18 120.5 n
C18 C19 H19 119.3 n
C20 C19 H19 119.3 n
C20 C21 H21 120.3 n
C22 C21 H21 120.3 n
C17 C22 H22 119.7 n
C21 C22 H22 119.7 n
O5 C23 H231 109.5 n
O5 C23 H232 109.5 n
H231 C23 H232 109.5 n
O5 C23 H233 109.5 n
H231 C23 H233 109.5 n
H232 C23 H233 109.5 n
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 O1 . 1.441(2) y
S O2 . 1.438(2) y
S C1 . 1.787(2) y
S C9 . 1.751(3) y
O3 C2 . 1.228(3) y
N1 N2 . 1.291(3) y
N1 C1 . 1.309(3) y
N2 C17 . 1.415(3) y
C1 C2 . 1.459(3) y
C2 C3 . 1.501(3) y
C3 C8 . 1.387(3) n
C3 C4 . 1.391(3) n
C4 C5 . 1.381(3) n
C5 C6 . 1.373(4) n
C6 C7 . 1.370(4) n
C7 C8 . 1.382(4) n
C9 C10 . 1.386(4) n
C9 C14 . 1.381(3) n
C10 C11 . 1.373(4) n
C11 C12 . 1.390(3) n
C12 C13 . 1.390(3) n
C13 C14 . 1.370(3) n
C17 C22 . 1.363(3) n
C17 C18 . 1.378(3) n
C18 C19 . 1.370(3) n
C19 C20 . 1.376(3) n
C20 C21 . 1.376(4) n
C21 C22 . 1.385(4) n
N3 C12 . 1.401(3) y
N3 C15 . 1.358(3) y
O4 C15 . 1.211(3) y
C15 C16 . 1.498(4) n
O5 C20 . 1.361(3) y
O5 C23 . 1.408(4) y
N2 H2 . .86(3) n
N3 H3 . .89(3) n
C4 H4 . .95 n
C5 H5 . .95 n
C6 H6 . .94 n
C7 H7 . .93 n
C8 H8 . .92 n
C10 H10 . .95 n
C11 H11 . .89 n
C13 H13 . .92 n
C14 H14 . .95 n
C16 H161 . .99 n
C16 H162 . .99 n
C16 H163 . .99 n
C18 H18 . .92 n
C19 H19 . .92 n
C21 H21 . .94 n
C22 H22 . .91 n
C23 H231 . .97 n
C23 H232 . .97 n
C23 H233 . .97 n
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
S O3 2.952(2) y
S N2 3.114(2) y
O1 C2 3.234(3) y
O2 C2 3.894(3) y
O1 N2 4.056(3) n
O2 N2 2.663(3) n
N2 C2 3.607(3) n
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
N2 H2 O2 . .86(3) 1.98(3) 2.663(3) 135(2)
N3 H3 O3 3_665 .89(3) 2.10(3) 2.991(3) 174(2)
C11 H11 O4 . .89 2.29 2.867(4) 122
C21 H21 O4 2_655 .94 2.55 3.474(4) 167
C14 H14 O4 1_565 .95 2.46 3.144(3) 129
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 8.4(3) y
S C1 N1 N2 -1.4(4) y
O1 S C1 C2 62.1(2) y
O1 S C1 N1 -114.9(2) y
O2 S C1 C2 -170.4(2) y
O2 S C1 N1 12.6(3) y
S C1 C2 C3 -173.0(2) n
N1 C1 C2 O3 -174.4(2) n
N1 C1 C2 C3 4.2(3) n
N2 N1 C1 C2 -178.4(2) n
C1 N1 N2 C17 175.6(2) n
C9 S C1 N1 128.0(2) n
C9 S C1 C2 -55.0(2) n
C12 N3 C15 O4 -3.9(4) n
C12 N3 C15 C16 177.2(2) n
C23 O5 C20 C21 -3.7(4) n
C23 O5 C20 C19 176.1(3) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21182043
