#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/08/2010867.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_2010867
loop_
_publ_author_name
'Hosomi, Hiroyuki'
'Ohba, Shigeru'
'Aoyama, Hiromu'
_publ_section_title
;N-Isopropyl-N-[(E)-2-phenylpropenyl]thiobenzamide and
 N-isopropyl-3-methoxy-N-[(E)-2-phenylpropenyl]thiobenzamide
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              e152
_journal_page_last               e153
_journal_paper_doi               10.1107/S0108270100004030
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C20 H23 N1 O1 S1'
_chemical_formula_sum            'C20 H23 N O S'
_chemical_formula_weight         325.47
_chemical_name_systematic
;
N-Isopropyl-3-methoxy-N-{(E)-2-phenyl-propenyl}-thiobenzamide
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_cell_angle_alpha                90
_cell_angle_beta                 105.390(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.4830(10)
_cell_length_b                   9.1110(10)
_cell_length_c                   21.611(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    248.0(10)
_cell_measurement_theta_max      29.4
_cell_measurement_theta_min      27.3
_cell_volume                     3698.6(6)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1993)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1999)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_measurement_device_type  'Rigaku AFC-7R'
_diffrn_measurement_method       θ-2θ
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  .028
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            4076
_diffrn_reflns_theta_max         75.0
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        1.0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.570
_exptl_absorpt_correction_T_max  .689
_exptl_absorpt_correction_T_min  .546
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(Coppens et al., 1965)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .3
_refine_diff_density_max         .24
_refine_diff_density_min         -.21
_refine_ls_extinction_coef       .00076(7)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3539
_refine_ls_R_factor_gt           .035
_refine_ls_shift/su_max          .001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.0496P)²+2.4391P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .101
_reflns_number_gt                3121
_reflns_number_total             3539
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qa0252.cif
_cod_data_source_block           II
_cod_original_cell_volume        3698.7(6)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C20 H23 N1 O1 S1'
_cod_database_code               2010867
_cod_database_fobs_code          2010867
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y,1/2-z
-x,-y,-z
x,-y,1/2+z
1/2+x,1/2+y,z
1/2-x,1/2+y,1/2-z
1/2-x,1/2-y,-z
1/2+x,1/2-y,1/2+z
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
S1 .60767(2) .13736(4) 1.02435(2) .04190(10) Uani d . 1.00 . . S
O2 .73603(7) .65110(10) 1.06995(7) .0634(4) Uani d . 1.00 . . O
N3 .55822(6) .21300(10) .90132(5) .0364(3) Uani d . 1.00 . . N
C4 .58841(7) .2536(2) .96234(6) .0333(3) Uani d . 1.00 . . C
C5 .60060(8) .4141(2) .97384(6) .0339(3) Uani d . 1.00 . . C
C6 .66277(9) .4648(2) 1.01515(7) .0395(3) Uani d . 1.00 . . C
C7 .67166(9) .6138(2) 1.02927(8) .0453(4) Uani d . 1.00 . . C
C8 .61760(10) .7118(2) 1.00276(9) .0511(4) Uani d . 1.00 . . C
C9 .55530(10) .6599(2) .96182(9) .0489(4) Uani d . 1.00 . . C
C10 .54620(9) .5133(2) .94661(8) .0411(3) Uani d . 1.00 . . C
C11 .7447(2) .8002(3) 1.09180(10) .0791(7) Uani d . 1.00 . . C
C12 .52430(10) .0669(2) .88499(8) .0467(4) Uani d . 1.00 . . C
C13 .57030(10) -.0330(2) .85760(10) .0636(5) Uani d . 1.00 . . C
C14 .45000(10) .0867(3) .84070(10) .0663(5) Uani d . 1.00 . . C
C15 .56519(8) .3027(2) .84872(7) .0356(3) Uani d . 1.00 . . C
C16 .62758(8) .3304(2) .83717(7) .0361(3) Uani d . 1.00 . . C
C17 .69640(10) .2677(2) .87600(10) .0540(4) Uani d . 1.00 . . C
C18 .63074(8) .4328(2) .78435(7) .0383(3) Uani d . 1.00 . . C
C19 .67280(10) .4032(2) .74310(10) .0623(5) Uani d . 1.00 . . C
C20 .6744(2) .4993(3) .69370(10) .0765(7) Uani d . 1.00 . . C
C21 .63480(10) .6254(3) .68510(10) .0727(6) Uani d . 1.00 . . C
C22 .59440(10) .6574(3) .72640(10) .0699(6) Uani d . 1.00 . . C
C23 .59225(9) .5617(2) .77584(9) .0504(4) Uani d . 1.00 . . C
H6 .6971(9) .401(2) 1.0332(8) .04544(6) Uiso d . 1.00 . . H
H8 .6235(10) .811(2) 1.0117(9) .05285(6) Uiso d . 1.00 . . H
H9 .5160(10) .729(2) .9450(9) .05611(6) Uiso d . 1.00 . . H
H10 .5022(9) .481(2) .9203(8) .03893(5) Uiso d . 1.00 . . H
H11A .793(2) .798(3) 1.1210(10) .09790(10) Uiso d . 1.00 . . H
H11B .7410(10) .870(3) 1.0550(10) .09890(10) Uiso d . 1.00 . . H
H11C .7100(10) .826(3) 1.1150(10) .07923(9) Uiso d . 1.00 . . H
H12 .5220(10) .030(2) .9252(9) .05467(6) Uiso d . 1.00 . . H
H13A .5460(10) -.130(3) .8460(10) .08349(9) Uiso d . 1.00 . . H
H13B .5770(10) .004(3) .8180(10) .07873(9) Uiso d . 1.00 . . H
H13C .6180(10) -.045(2) .8880(10) .07451(8) Uiso d . 1.00 . . H
H14A .4240(10) .158(2) .8590(10) .06785(8) Uiso d . 1.00 . . H
H14B .4510(10) .122(3) .7970(10) .08503(9) Uiso d . 1.00 . . H
H14C .4240(10) -.004(3) .8370(10) .08456(9) Uiso d . 1.00 . . H
H15 .5232(9) .338(2) .8214(8) .04014(5) Uiso d . 1.00 . . H
H17A .6910(10) .198(3) .9050(10) .06879(8) Uiso d . 1.00 . . H
H17B .7230(10) .222(3) .8500(10) .08794(9) Uiso d . 1.00 . . H
H17C .731(2) .343(4) .899(2) .12810(10) Uiso d . 1.00 . . H
H19 .7000(10) .313(3) .7490(10) .07761(9) Uiso d . 1.00 . . H
H20 .7030(10) .476(3) .6680(10) .09031(10) Uiso d . 1.00 . . H
H21 .6370(10) .693(3) .6510(10) .08788(9) Uiso d . 1.00 . . H
H22 .5670(10) .747(3) .7230(10) .08391(9) Uiso d . 1.00 . . H
H23 .5650(10) .585(2) .8050(10) .06052(7) Uiso d . 1.00 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .018 .009
;International Tables for Crystallography
(1992, Vol. C)
;
H H .000 .000
;International Tables for Crystallography
(1992, Vol. C)
;
N N .031 .018
;International Tables for Crystallography
(1992, Vol. C)
;
O O .049 .032
;International Tables for Crystallography
(1992, Vol. C)
;
S S .333 .557
;International Tables for Crystallography
(1992, Vol. C)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 O2 C11 1_555 1_555 1_555 117.0(2) no
C4 N3 C12 1_555 1_555 1_555 122.00(10) no
C4 N3 C15 1_555 1_555 1_555 120.70(10) no
C12 N3 C15 1_555 1_555 1_555 116.80(10) no
S1 C4 N3 1_555 1_555 1_555 123.90(10) no
S1 C4 C5 1_555 1_555 1_555 119.70(10) no
N3 C4 C5 1_555 1_555 1_555 116.20(10) no
C4 C5 C6 1_555 1_555 1_555 120.60(10) no
C4 C5 C10 1_555 1_555 1_555 119.60(10) no
C6 C5 C10 1_555 1_555 1_555 119.50(10) no
C5 C6 C7 1_555 1_555 1_555 120.30(10) no
C5 C6 H6 1_555 1_555 1_555 119.0(10) no
C7 C6 H6 1_555 1_555 1_555 120.0(10) no
O2 C7 C6 1_555 1_555 1_555 115.00(10) no
O2 C7 C8 1_555 1_555 1_555 124.90(10) no
C6 C7 C8 1_555 1_555 1_555 120.10(10) no
C7 C8 C9 1_555 1_555 1_555 119.10(10) no
C7 C8 H8 1_555 1_555 1_555 120.0(10) no
C9 C8 H8 1_555 1_555 1_555 120.0(10) no
C8 C9 C10 1_555 1_555 1_555 121.4(2) no
C8 C9 H9 1_555 1_555 1_555 118.0(10) no
C10 C9 H9 1_555 1_555 1_555 119.0(10) no
C5 C10 C9 1_555 1_555 1_555 119.40(10) no
C5 C10 H10 1_555 1_555 1_555 121.0(10) no
C9 C10 H10 1_555 1_555 1_555 119.0(10) no
O2 C11 H11A 1_555 1_555 1_555 101.0(10) no
O2 C11 H11B 1_555 1_555 1_555 110.0(10) no
O2 C11 H11C 1_555 1_555 1_555 111.0(10) no
H11A C11 H11B 1_555 1_555 1_555 111(2) no
H11A C11 H11C 1_555 1_555 1_555 110(2) no
H11B C11 H11C 1_555 1_555 1_555 111(2) no
N3 C12 C13 1_555 1_555 1_555 111.2(2) no
N3 C12 C14 1_555 1_555 1_555 109.40(10) no
N3 C12 H12 1_555 1_555 1_555 103.0(10) no
C13 C12 C14 1_555 1_555 1_555 113.0(2) no
C13 C12 H12 1_555 1_555 1_555 109.0(10) no
C14 C12 H12 1_555 1_555 1_555 110.0(10) no
C12 C13 H13A 1_555 1_555 1_555 109.0(10) no
C12 C13 H13B 1_555 1_555 1_555 111.0(10) no
C12 C13 H13C 1_555 1_555 1_555 110.0(10) no
H13A C13 H13B 1_555 1_555 1_555 104(2) no
H13A C13 H13C 1_555 1_555 1_555 111.0(10) no
H13B C13 H13C 1_555 1_555 1_555 108(2) no
C12 C14 H14A 1_555 1_555 1_555 109.0(10) no
C12 C14 H14B 1_555 1_555 1_555 111.0(10) no
C12 C14 H14C 1_555 1_555 1_555 110.0(10) no
H14A C14 H14B 1_555 1_555 1_555 108.0(10) no
H14A C14 H14C 1_555 1_555 1_555 107(2) no
H14B C14 H14C 1_555 1_555 1_555 109(2) no
N3 C15 C16 1_555 1_555 1_555 122.70(10) no
N3 C15 H15 1_555 1_555 1_555 116.0(10) no
C16 C15 H15 1_555 1_555 1_555 120.0(10) no
C15 C16 C17 1_555 1_555 1_555 123.4(2) no
C15 C16 C18 1_555 1_555 1_555 119.30(10) no
C17 C16 C18 1_555 1_555 1_555 117.2(2) no
C16 C17 H17A 1_555 1_555 1_555 113.0(10) no
C16 C17 H17B 1_555 1_555 1_555 112.0(10) no
C16 C17 H17C 1_555 1_555 1_555 114.0(10) no
H17A C17 H17B 1_555 1_555 1_555 106(2) no
H17A C17 H17C 1_555 1_555 1_555 108(2) no
H17B C17 H17C 1_555 1_555 1_555 100(2) no
C16 C18 C19 1_555 1_555 1_555 121.50(10) no
C16 C18 C23 1_555 1_555 1_555 120.3(2) no
C19 C18 C23 1_555 1_555 1_555 118.2(2) no
C18 C19 C20 1_555 1_555 1_555 120.7(2) no
C18 C19 H19 1_555 1_555 1_555 118.0(10) no
C20 C19 H19 1_555 1_555 1_555 120.0(10) no
C19 C20 C21 1_555 1_555 1_555 120.5(3) no
C19 C20 H20 1_555 1_555 1_555 117.0(10) no
C21 C20 H20 1_555 1_555 1_555 121.0(10) no
C20 C21 C22 1_555 1_555 1_555 119.4(2) no
C20 C21 H21 1_555 1_555 1_555 120.0(10) no
C22 C21 H21 1_555 1_555 1_555 120.0(10) no
C21 C22 C23 1_555 1_555 1_555 120.5(2) no
C21 C22 H22 1_555 1_555 1_555 121.0(10) no
C23 C22 H22 1_555 1_555 1_555 117.0(10) no
C18 C23 C22 1_555 1_555 1_555 120.7(2) no
C18 C23 H23 1_555 1_555 1_555 118.0(10) no
C22 C23 H23 1_555 1_555 1_555 120.0(10) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C4 . . 1.6710(10) yes
O2 C7 . . 1.370(2) no
O2 C11 . . 1.434(3) no
N3 C4 . . 1.345(2) yes
N3 C12 . . 1.487(2) no
N3 C15 . . 1.435(2) yes
C4 C5 . . 1.492(2) no
C5 C6 . . 1.380(2) no
C5 C10 . . 1.398(2) no
C6 C7 . . 1.392(2) no
C6 H6 . . .89(2) no
C7 C8 . . 1.384(2) no
C8 C9 . . 1.382(3) no
C8 H8 . . .93(2) no
C9 C10 . . 1.376(2) no
C9 H9 . . .98(2) no
C10 H10 . . .94(2) no
C11 H11A . . .97(3) no
C11 H11B . . 1.01(3) no
C11 H11C . . .97(3) no
C12 C13 . . 1.505(3) no
C12 C14 . . 1.521(3) no
C12 H12 . . .94(2) no
C13 H13A . . 1.00(2) no
C13 H13B . . .95(3) no
C13 H13C . . 1.00(2) no
C14 H14A . . .97(2) no
C14 H14B . . 1.00(3) no
C14 H14C . . .96(3) no
C15 C16 . . 1.329(2) yes
C15 H15 . . .93(2) no
C16 C17 . . 1.495(2) no
C16 C18 . . 1.488(2) no
C17 H17A . . .92(2) no
C17 H17B . . .95(3) no
C17 H17C . . 1.00(3) no
C18 C19 . . 1.387(3) no
C18 C23 . . 1.379(2) no
C19 C20 . . 1.388(3) no
C19 H19 . . .97(2) no
C20 C21 . . 1.368(4) no
C20 H20 . . .91(3) no
C21 C22 . . 1.369(4) no
C21 H21 . . .98(3) no
C22 C23 . . 1.389(3) no
C22 H22 . . .96(2) no
C23 H23 . . .95(2) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21107209
