#------------------------------------------------------------------------------
#$Date: 2016-06-18 04:40:24 +0300 (Sat, 18 Jun 2016) $
#$Revision: 183688 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/34/1543476.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_1543476
loop_
_publ_author_name
'Mague, Joel T.'
'Mohamed, Shaaban K.'
'Akkurt, Mehmet'
'Abdel-Raheem, Eman M. M.'
'Albayati, Mustafa R.'
_publ_section_title
;
 1-((E)-{2-[4-(2-{(1E)-[(carbamothioylamino)imino]methyl}phenoxy)butoxy]benzylidene}amino)thiourea
 dimethyl sulfoxide disolvate
;
_journal_coeditor_code           HG4009
_journal_issue                   6
_journal_name_full               IUCrData
_journal_page_first              x160946
_journal_paper_doi               10.1107/S2414314616009469
_journal_volume                  1
_journal_year                    2016
_chemical_formula_iupac          'C20 H24 N6 O2 S2, 2C2 H6 O S'
_chemical_formula_moiety         'C20 H24 N6 O2 S2, 2(C2 H6 O S)'
_chemical_formula_sum            'C24 H36 N6 O4 S4'
_chemical_formula_weight         600.83
_chemical_name_systematic
;1-((E)-{2-[4-(2-{(1E)-[(Carbamothioylamino)imino]methyl}phenoxy)butoxy]benzylidene}amino)thiourea
dimethyl sulfoxide disolvate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                112.9840(10)
_cell_angle_beta                 98.1630(10)
_cell_angle_gamma                96.9090(10)
_cell_formula_units_Z            1
_cell_length_a                   7.2571(2)
_cell_length_b                   9.7909(2)
_cell_length_c                   12.0060(2)
_cell_measurement_reflns_used    6799
_cell_measurement_temperature    150.(2)
_cell_measurement_theta_max      72.1432
_cell_measurement_theta_min      4.0880
_cell_volume                     762.80(3)
_computing_cell_refinement
;
SAINT (Bruker, 2015)
;
_computing_data_collection
;
APEX2 (Bruker, 2015)
;
_computing_data_reduction
;
SAINT  (Bruker, 2015)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8374
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         72.138
_diffrn_reflns_theta_min         4.976
_exptl_absorpt_coefficient_mu    3.188
_exptl_absorpt_correction_T_max  0.76
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thick plate'
_exptl_crystal_F_000             318
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.092
_refine_diff_density_max         0.884
_refine_diff_density_min         -0.678
_refine_ls_extinction_coef       0.0061(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2932
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0905P)²+0.7660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1582
_refine_ls_wR_factor_ref         0.1622
_reflns_number_gt                2679
_reflns_number_total             2932
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hg4009sup1.cif
_cod_data_source_block           I
_cod_database_code               1543476
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.514
_shelx_estimated_absorpt_t_max   0.758
loop_
_space_group_symop_operation_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.18022(10) 0.04286(7) -0.12107(6) 0.0368(2) Uani d 1 . .
O O1 0.1735(3) 0.2497(2) 0.51184(15) 0.0357(4) Uani d 1 . .
N N1 0.2228(3) 0.3358(2) 0.22135(18) 0.0304(5) Uani d 1 . .
N N2 0.1727(3) 0.2071(2) 0.11133(19) 0.0332(5) Uani d 1 . .
H H2A 0.0875 0.1248 0.1011 0.040 Uiso d 1 . .
N N3 0.3466(3) 0.3281(3) 0.0209(2) 0.0390(5) Uani d 1 . .
H H3A 0.3769 0.4102 0.0950 0.047 Uiso d 1 . .
H H3B 0.3708 0.3273 -0.0516 0.047 Uiso d 1 . .
C C1 0.2179(3) 0.4002(3) 0.5403(2) 0.0300(5) Uani d 1 . .
C C2 0.2562(4) 0.5137(3) 0.6594(2) 0.0370(6) Uani d 1 . .
H H2 0.2490 0.4888 0.7279 0.044 Uiso calc 1 . .
C C3 0.3048(4) 0.6632(3) 0.6779(3) 0.0411(7) Uani d 1 . .
H H3 0.3303 0.7408 0.7593 0.049 Uiso calc 1 . .
C C4 0.3165(4) 0.7009(3) 0.5790(3) 0.0431(7) Uani d 1 . .
H H4 0.3500 0.8038 0.5926 0.052 Uiso calc 1 . .
C C5 0.2792(4) 0.5879(3) 0.4600(3) 0.0378(6) Uani d 1 . .
H H5 0.2889 0.6139 0.3923 0.045 Uiso calc 1 . .
C C6 0.2279(3) 0.4369(3) 0.4385(2) 0.0284(5) Uani d 1 . .
C C7 0.1356(4) 0.2043(3) 0.6080(2) 0.0372(6) Uani d 1 . .
H H7A 0.0272 0.2458 0.6410 0.045 Uiso calc 1 . .
H H7B 0.2480 0.2418 0.6766 0.045 Uiso calc 1 . .
C C8 0.0894(4) 0.0336(3) 0.5507(2) 0.0383(6) Uani d 1 . .
H H8A 0.0738 -0.0015 0.6164 0.046 Uiso calc 1 . .
H H8B 0.1978 -0.0051 0.5157 0.046 Uiso calc 1 . .
C C9 0.1840(3) 0.3150(3) 0.3144(2) 0.0297(5) Uani d 1 . .
H H9 0.1248 0.2170 0.3027 0.036 Uiso calc 1 . .
C C10 0.2385(4) 0.2042(3) 0.0115(2) 0.0301(5) Uani d 1 . .
S S2 0.29091(12) 0.73336(10) 0.18388(10) 0.0576(3) Uani d 1 . .
O O2 0.4525(3) 0.6510(2) 0.16444(18) 0.0268(5) Uani d 0.831(3) A 1
C C11 0.3689(11) 0.9102(8) 0.2855(8) 0.114(2) Uani d 0.831(3) A 1
H H11A 0.2621 0.9631 0.2976 0.172 Uiso calc 0.831(3) A 1
H H11B 0.4297 0.9117 0.3644 0.172 Uiso calc 0.831(3) A 1
H H11C 0.4612 0.9606 0.2549 0.172 Uiso calc 0.831(3) A 1
C C12 0.2625(10) 0.7934(10) 0.0557(7) 0.101(2) Uani d 0.831(3) A 1
H H12A 0.1582 0.8491 0.0607 0.151 Uiso calc 0.831(3) A 1
H H12B 0.3802 0.8588 0.0617 0.151 Uiso calc 0.831(3) A 1
H H12C 0.2338 0.7041 -0.0233 0.151 Uiso calc 0.831(3) A 1
O O2A 0.0956(8) 0.6372(9) 0.1245(8) 0.0268(5) Uani d 0.169(3) A 2
C C11A 0.207(5) 0.760(4) 0.310(2) 0.114(2) Uani d 0.169(3) A 2
H H11D 0.3039 0.8269 0.3829 0.172 Uiso calc 0.169(3) A 2
H H11E 0.0943 0.8055 0.3075 0.172 Uiso calc 0.169(3) A 2
H H11F 0.1722 0.6622 0.3142 0.172 Uiso calc 0.169(3) A 2
C C12A 0.334(5) 0.907(3) 0.158(4) 0.101(2) Uani d 0.169(3) A 2
H H12D 0.4631 0.9624 0.1997 0.151 Uiso calc 0.169(3) A 2
H H12E 0.3171 0.8803 0.0693 0.151 Uiso calc 0.169(3) A 2
H H12F 0.2430 0.9705 0.1919 0.151 Uiso calc 0.169(3) A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C1 O1 C7 . . 118.3(2)
C9 N1 N2 . . 114.0(2)
C10 N2 N1 . . 120.4(2)
C10 N2 H2A . . 117.1
N1 N2 H2A . . 122.4
C10 N3 H3A . . 119.0
C10 N3 H3B . . 115.2
H3A N3 H3B . . 125.2
O1 C1 C2 . . 124.6(2)
O1 C1 C6 . . 115.2(2)
C2 C1 C6 . . 120.2(2)
C3 C2 C1 . . 119.7(3)
C3 C2 H2 . . 120.2
C1 C2 H2 . . 120.2
C4 C3 C2 . . 120.7(3)
C4 C3 H3 . . 119.6
C2 C3 H3 . . 119.6
C3 C4 C5 . . 119.8(3)
C3 C4 H4 . . 120.1
C5 C4 H4 . . 120.1
C4 C5 C6 . . 120.7(3)
C4 C5 H5 . . 119.6
C6 C5 H5 . . 119.6
C5 C6 C1 . . 118.9(2)
C5 C6 C9 . . 122.4(2)
C1 C6 C9 . . 118.8(2)
O1 C7 C8 . . 106.9(2)
O1 C7 H7A . . 110.3
C8 C7 H7A . . 110.3
O1 C7 H7B . . 110.3
C8 C7 H7B . . 110.3
H7A C7 H7B . . 108.6
C7 C8 C8 . 2_556 113.8(3)
C7 C8 H8A . . 108.8
C8 C8 H8A 2_556 . 108.8
C7 C8 H8B . . 108.8
C8 C8 H8B 2_556 . 108.8
H8A C8 H8B . . 107.7
N1 C9 C6 . . 122.0(2)
N1 C9 H9 . . 119.0
C6 C9 H9 . . 119.0
N3 C10 N2 . . 118.0(2)
N3 C10 S1 . . 122.66(19)
N2 C10 S1 . . 119.34(18)
O2 S2 C11 . . 110.1(3)
O2A S2 C11A . . 81.0(14)
O2A S2 C12A . . 114.8(11)
C11A S2 C12A . . 112.6(17)
O2 S2 C12 . . 103.4(2)
C11 S2 C12 . . 91.0(4)
S2 C11 H11A . . 109.5
S2 C11 H11B . . 109.5
H11A C11 H11B . . 109.5
S2 C11 H11C . . 109.5
H11A C11 H11C . . 109.5
H11B C11 H11C . . 109.5
S2 C12 H12A . . 109.5
S2 C12 H12B . . 109.5
H12A C12 H12B . . 109.5
S2 C12 H12C . . 109.5
H12A C12 H12C . . 109.5
H12B C12 H12C . . 109.5
S2 C11A H11D . . 109.5
S2 C11A H11E . . 109.5
H11D C11A H11E . . 109.5
S2 C11A H11F . . 109.5
H11D C11A H11F . . 109.5
H11E C11A H11F . . 109.5
S2 C12A H12D . . 109.5
S2 C12A H12E . . 109.5
H12D C12A H12E . . 109.5
S2 C12A H12F . . 109.5
H12D C12A H12F . . 109.5
H12E C12A H12F . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 C10 . 1.700(3)
O1 C1 . 1.360(3)
O1 C7 . 1.438(3)
N1 C9 . 1.274(3)
N1 N2 . 1.385(3)
N2 C10 . 1.343(3)
N2 H2A . 0.9101
N3 C10 . 1.319(3)
N3 H3A . 0.9100
N3 H3B . 0.9101
C1 C2 . 1.389(4)
C1 C6 . 1.411(3)
C2 C3 . 1.385(4)
C2 H2 . 0.9500
C3 C4 . 1.384(4)
C3 H3 . 0.9500
C4 C5 . 1.387(4)
C4 H4 . 0.9500
C5 C6 . 1.390(4)
C5 H5 . 0.9500
C6 C9 . 1.460(3)
C7 C8 . 1.510(4)
C7 H7A . 0.9900
C7 H7B . 0.9900
C8 C8 2_556 1.523(5)
C8 H8A . 0.9900
C8 H8B . 0.9900
C9 H9 . 0.9500
S2 O2 . 1.496(2)
S2 O2A . 1.508(4)
S2 C11 . 1.651(7)
S2 C11A . 1.651(8)
S2 C12A . 1.841(7)
S2 C12 . 1.844(6)
C11 H11A . 0.9800
C11 H11B . 0.9800
C11 H11C . 0.9800
C12 H12A . 0.9800
C12 H12B . 0.9800
C12 H12C . 0.9800
C11A H11D . 0.9800
C11A H11E . 0.9800
C11A H11F . 0.9800
C12A H12D . 0.9800
C12A H12E . 0.9800
C12A H12F . 0.9800
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 H2A S1 2 0.91 2.49 3.371(2) 163
N3 H3A O2 . 0.91 2.14 2.887(3) 139
N3 H3B O2 2_665 0.91 2.04 2.885(3) 153
C7 H7B O2 2_666 0.99 2.49 3.471(3) 174
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_site_symmetry_4
_geom_torsion
C9 N1 N2 C10 . -166.5(2)
C7 O1 C1 C2 . 9.7(4)
C7 O1 C1 C6 . -171.7(2)
O1 C1 C2 C3 . 178.3(2)
C6 C1 C2 C3 . -0.2(4)
C1 C2 C3 C4 . -0.3(4)
C2 C3 C4 C5 . 0.0(5)
C3 C4 C5 C6 . 0.8(4)
C4 C5 C6 C1 . -1.3(4)
C4 C5 C6 C9 . 178.8(2)
O1 C1 C6 C5 . -177.7(2)
C2 C1 C6 C5 . 1.0(4)
O1 C1 C6 C9 . 2.2(3)
C2 C1 C6 C9 . -179.1(2)
C1 O1 C7 C8 . 179.6(2)
O1 C7 C8 C8 2_556 -63.5(4)
N2 N1 C9 C6 . 179.4(2)
C5 C6 C9 N1 . 13.0(4)
C1 C6 C9 N1 . -166.9(2)
N1 N2 C10 N3 . -1.9(4)
N1 N2 C10 S1 . 178.10(18)

_cod_database_fobs_code 1543476
