#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/75/2217510.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_2217510
loop_
_publ_author_name
'Kinghat, Rodolphe'
'Boudiba, Hamid'
'Khatyr, Abderrahim'
'Knorr, Michael'
'Kubicki, Marek M.'
_publ_section_title
;
 4,4-Bis(4-methylphenylsulfanyl)-1,1-diphenyl-2-azabuta-1,3-diene
;
_journal_coeditor_code           GW2031
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o370
_journal_page_last               o370
_journal_paper_doi               10.1107/S1600536807066615
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C29 H25 N S2'
_chemical_formula_moiety         'C29 H25 N S2'
_chemical_formula_sum            'C29 H25 N S2'
_chemical_formula_weight         451.66
_chemical_melting_point          382
_chemical_name_systematic
;
4,4-Bis(4-methylphenylsulfanyl)-1,1-diphenyl-2-azabuta-1,3-diene
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                101.7371(8)
_cell_angle_beta                 98.2522(7)
_cell_angle_gamma                93.0400(10)
_cell_formula_units_Z            2
_cell_length_a                   6.9340(10)
_cell_length_b                   12.3009(2)
_cell_length_c                   14.4247(3)
_cell_measurement_reflns_used    3954
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1187.85(17)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'KappaCCD Server Software (Nonius, 1997)'
_computing_data_reduction
;
DENZO (Otwinowski & Minor, 1997) and SCALEPACK (Otwinowski & Minor,
1997)
;
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7710
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_min         1.46
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.245
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         5329
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0329P)²+0.5208P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0892
_reflns_number_gt                4695
_reflns_number_total             5329
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gw2031.cif
_cod_data_source_block           I
_cod_original_cell_volume        1187.90(4)
_cod_database_code               2217510
_cod_database_fobs_code          2217510
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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
S S1 0.22781(5) 0.37867(3) 0.35024(2) 0.02290(9) Uani d . 1
S S2 0.43297(4) 0.52776(3) 0.23783(2) 0.02161(9) Uani d . 1
N N 0.48657(16) 0.21771(9) 0.26950(8) 0.0221(2) Uani d . 1
C C1 0.58163(18) 0.13424(11) 0.23639(9) 0.0204(3) Uani d . 1
C C2 0.50043(19) 0.31661(11) 0.23787(10) 0.0227(3) Uani d . 1
C C3 0.39300(18) 0.40002(11) 0.27163(9) 0.0200(3) Uani d . 1
C C4 0.71038(19) 0.13495(10) 0.16171(9) 0.0206(3) Uani d . 1
C C5 0.6304(2) 0.12895(14) 0.06658(11) 0.0328(3) Uani d . 1
H H5 0.4953 0.1238 0.0489 0.039 Uiso calc R 1
C C6 0.7506(3) 0.13066(16) -0.00219(12) 0.0415(4) Uani d . 1
H H6 0.6960 0.1270 -0.0656 0.050 Uiso calc R 1
C C7 0.9508(2) 0.13778(14) 0.02340(12) 0.0364(4) Uani d . 1
H H7 1.0312 0.1378 -0.0230 0.044 Uiso calc R 1
C C8 1.0317(2) 0.14488(13) 0.11728(12) 0.0350(3) Uani d . 1
H H8 1.1670 0.1506 0.1345 0.042 Uiso calc R 1
C C9 0.9128(2) 0.14354(12) 0.18644(11) 0.0287(3) Uani d . 1
H H9 0.9686 0.1484 0.2499 0.034 Uiso calc R 1
C C10 0.56071(18) 0.03303(11) 0.27658(9) 0.0207(3) Uani d . 1
C C11 0.6700(2) -0.05758(11) 0.25308(10) 0.0250(3) Uani d . 1
H H11 0.7553 -0.0568 0.2089 0.030 Uiso calc R 1
C C12 0.6528(2) -0.14933(12) 0.29507(11) 0.0293(3) Uani d . 1
H H12 0.7284 -0.2087 0.2799 0.035 Uiso calc R 1
C C13 0.5238(2) -0.15238(12) 0.35923(11) 0.0285(3) Uani d . 1
H H13 0.5126 -0.2136 0.3874 0.034 Uiso calc R 1
C C14 0.4112(2) -0.06400(13) 0.38151(12) 0.0322(3) Uani d . 1
H H14 0.3228 -0.0664 0.4240 0.039 Uiso calc R 1
C C15 0.4296(2) 0.02781(12) 0.34092(11) 0.0290(3) Uani d . 1
H H15 0.3537 0.0869 0.3566 0.035 Uiso calc R 1
C C16 0.19592(18) 0.55484(11) 0.18701(9) 0.0200(3) Uani d . 1
C C17 0.05190(19) 0.47143(11) 0.13858(10) 0.0231(3) Uani d . 1
H H17 0.0744 0.3969 0.1344 0.028 Uiso calc R 1
C C18 -0.1256(2) 0.50030(12) 0.09652(10) 0.0258(3) Uani d . 1
H H18 -0.2222 0.4443 0.0652 0.031 Uiso calc R 1
C C19 -0.1623(2) 0.61123(12) 0.10010(10) 0.0249(3) Uani d . 1
C C20 -0.0167(2) 0.69289(12) 0.14901(10) 0.0269(3) Uani d . 1
H H20 -0.0387 0.7675 0.1528 0.032 Uiso calc R 1
C C21 0.1609(2) 0.66593(11) 0.19237(10) 0.0255(3) Uani d . 1
H H21 0.2563 0.7221 0.2249 0.031 Uiso calc R 1
C C22 -0.3522(2) 0.64249(15) 0.05100(12) 0.0328(3) Uani d . 1
C C23 0.16434(19) 0.51460(10) 0.39797(9) 0.0195(3) Uani d . 1
C C24 -0.02989(19) 0.53814(11) 0.38031(9) 0.0217(3) Uani d . 1
H H24 -0.1223 0.4848 0.3408 0.026 Uiso calc R 1
C C25 -0.08547(19) 0.64104(11) 0.42158(10) 0.0233(3) Uani d . 1
H H25 -0.2158 0.6559 0.4098 0.028 Uiso calc R 1
C C26 0.0502(2) 0.72288(11) 0.48054(9) 0.0222(3) Uani d . 1
C C27 0.2438(2) 0.69758(11) 0.49862(9) 0.0231(3) Uani d . 1
H H27 0.3362 0.7509 0.5383 0.028 Uiso calc R 1
C C28 0.30109(19) 0.59443(11) 0.45858(9) 0.0218(3) Uani d . 1
H H28 0.4305 0.5786 0.4721 0.026 Uiso calc R 1
C C29 -0.0105(3) 0.83537(13) 0.52391(12) 0.0316(3) Uani d . 1
H H2 0.587(2) 0.3271(13) 0.1916(11) 0.023(4) Uiso d . 1
H H221 -0.460(3) 0.6112(18) 0.0711(16) 0.060(6) Uiso d . 1
H H222 -0.370(3) 0.6152(19) -0.0180(18) 0.065(7) Uiso d . 1
H H223 -0.357(3) 0.722(2) 0.0618(17) 0.075(7) Uiso d . 1
H H291 -0.049(3) 0.8755(17) 0.4753(15) 0.050(5) Uiso d . 1
H H292 0.094(3) 0.8815(18) 0.5682(15) 0.055(6) Uiso d . 1
H H293 -0.120(3) 0.8270(19) 0.5548(16) 0.066(7) Uiso d . 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 '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
C3 S1 C23 104.31(6) n
C3 S2 C16 103.68(6) n
C1 N C2 121.26(12) n
N C1 C10 117.10(12) n
N C1 C4 123.91(12) n
C10 C1 C4 118.98(11) n
C3 C2 N 119.27(12) n
C3 C2 H2 119.6(9) ?
N C2 H2 121.2(9) ?
C2 C3 S2 117.32(10) n
C2 C3 S1 119.54(10) n
S2 C3 S1 123.10(8) n
C9 C4 C5 118.69(13) ?
C9 C4 C1 120.58(12) ?
C5 C4 C1 120.73(12) ?
C6 C5 C4 120.46(14) ?
C6 C5 H5 119.8 ?
C4 C5 H5 119.8 ?
C7 C6 C5 120.06(15) ?
C7 C6 H6 120.0 ?
C5 C6 H6 120.0 ?
C8 C7 C6 120.05(14) ?
C8 C7 H7 120.0 ?
C6 C7 H7 120.0 ?
C7 C8 C9 120.25(14) ?
C7 C8 H8 119.9 ?
C9 C8 H8 119.9 ?
C8 C9 C4 120.48(14) ?
C8 C9 H9 119.8 ?
C4 C9 H9 119.8 ?
C11 C10 C15 118.28(12) ?
C11 C10 C1 122.05(12) ?
C15 C10 C1 119.66(12) ?
C12 C11 C10 120.62(13) ?
C12 C11 H11 119.7 ?
C10 C11 H11 119.7 ?
C13 C12 C11 120.18(13) ?
C13 C12 H12 119.9 ?
C11 C12 H12 119.9 ?
C12 C13 C14 119.75(13) ?
C12 C13 H13 120.1 ?
C14 C13 H13 120.1 ?
C15 C14 C13 120.26(14) ?
C15 C14 H14 119.9 ?
C13 C14 H14 119.9 ?
C14 C15 C10 120.89(13) ?
C14 C15 H15 119.6 ?
C10 C15 H15 119.6 ?
C21 C16 C17 119.68(12) ?
C21 C16 S2 116.76(10) ?
C17 C16 S2 123.46(10) ?
C18 C17 C16 119.57(12) ?
C18 C17 H17 120.2 ?
C16 C17 H17 120.2 ?
C17 C18 C19 121.53(13) ?
C17 C18 H18 119.2 ?
C19 C18 H18 119.2 ?
C20 C19 C18 117.82(12) ?
C20 C19 C22 120.64(13) ?
C18 C19 C22 121.53(14) ?
C21 C20 C19 121.59(13) ?
C21 C20 H20 119.2 ?
C19 C20 H20 119.2 ?
C20 C21 C16 119.80(13) ?
C20 C21 H21 120.1 ?
C16 C21 H21 120.1 ?
C19 C22 H221 111.6(13) ?
C19 C22 H222 111.9(13) ?
H221 C22 H222 105.5(18) ?
C19 C22 H223 111.4(14) ?
H221 C22 H223 109.5(19) ?
H222 C22 H223 106.6(19) ?
C24 C23 C28 119.57(12) ?
C24 C23 S1 118.78(10) ?
C28 C23 S1 121.44(10) ?
C25 C24 C23 119.96(12) ?
C25 C24 H24 120.0 ?
C23 C24 H24 120.0 ?
C24 C25 C26 121.25(12) ?
C24 C25 H25 119.4 ?
C26 C25 H25 119.4 ?
C27 C26 C25 118.15(12) ?
C27 C26 C29 120.85(13) ?
C25 C26 C29 121.01(13) ?
C28 C27 C26 121.20(12) ?
C28 C27 H27 119.4 ?
C26 C27 H27 119.4 ?
C27 C28 C23 119.84(12) ?
C27 C28 H28 120.1 ?
C23 C28 H28 120.1 ?
C26 C29 H291 110.6(12) ?
C26 C29 H292 112.6(13) ?
H291 C29 H292 106.3(17) ?
C26 C29 H293 110.2(14) ?
H291 C29 H293 106.8(18) ?
H292 C29 H293 110.1(18) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C3 1.7689(13) n
S1 C23 1.7776(13) n
S2 C3 1.7572(13) n
S2 C16 1.7781(13) n
N C1 1.2959(17) n
N C2 1.3869(17) n
C1 C10 1.4851(18) n
C1 C4 1.4955(18) n
C2 C3 1.3515(18) n
C2 H2 0.983(15) ?
C4 C9 1.3904(19) ?
C4 C5 1.3902(19) ?
C5 C6 1.387(2) ?
C5 H5 0.9300 ?
C6 C7 1.378(2) ?
C6 H6 0.9300 ?
C7 C8 1.373(2) ?
C7 H7 0.9300 ?
C8 C9 1.385(2) ?
C8 H8 0.9300 ?
C9 H9 0.9300 ?
C10 C11 1.3934(18) ?
C10 C15 1.3974(19) ?
C11 C12 1.3927(19) ?
C11 H11 0.9300 ?
C12 C13 1.381(2) ?
C12 H12 0.9300 ?
C13 C14 1.384(2) ?
C13 H13 0.9300 ?
C14 C15 1.382(2) ?
C14 H14 0.9300 ?
C15 H15 0.9300 ?
C16 C21 1.3892(19) ?
C16 C17 1.3919(19) ?
C17 C18 1.3890(19) ?
C17 H17 0.9300 ?
C18 C19 1.393(2) ?
C18 H18 0.9300 ?
C19 C20 1.388(2) ?
C19 C22 1.5098(19) ?
C20 C21 1.3873(19) ?
C20 H20 0.9300 ?
C21 H21 0.9300 ?
C22 H221 0.93(2) ?
C22 H222 0.97(2) ?
C22 H223 0.96(3) ?
C23 C24 1.3912(18) ?
C23 C28 1.3936(18) ?
C24 C25 1.3843(19) ?
C24 H24 0.9300 ?
C25 C26 1.3941(19) ?
C25 H25 0.9300 ?
C26 C27 1.3942(19) ?
C26 C29 1.5062(19) ?
C27 C28 1.3864(19) ?
C27 H27 0.9300 ?
C28 H28 0.9300 ?
C29 H291 0.95(2) ?
C29 H292 0.97(2) ?
C29 H293 0.95(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21119273
