#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/52/2225274.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_2225274
loop_
_publ_author_name
'de Lima, Geraldo M.'
'Harrison, William T. A.'
'Tiekink, Edward R. T.'
'Wardell, James L.'
'Wardell, Solange M. S. V.'
_publ_section_title
(E)-1-Phenyl-2-({5-[(1E)-(2-phenylhydrazin-1-ylidene)methyl]-2-thienyl}methylidene)hydrazine
_journal_coeditor_code           HG2637
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o504
_journal_page_last               o505
_journal_paper_doi               10.1107/S1600536810003302
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C18 H16 N4 S'
_chemical_formula_moiety         'C18 H16 N4 S'
_chemical_formula_sum            'C18 H16 N4 S'
_chemical_formula_weight         320.41
_chemical_name_systematic
;
(E)-1-Phenyl-2-({5-[(1E)-(2-phenylhydrazin-1-ylidene)methyl]-
2-thienyl}methylidene)hydrazine
;
_space_group_IT_number           145
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  'P 32'
_symmetry_space_group_name_H-M   'P 32'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   15.6495(6)
_cell_length_b                   15.6495(6)
_cell_length_c                   5.9335(10)
_cell_measurement_reflns_used    8754
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     1258.5(2)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  '10 cm confocal mirrors'
_diffrn_radiation_source         'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.059
_diffrn_reflns_av_sigmaI/netI    0.048
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            11400
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.0
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.22
_refine_ls_abs_structure_details 'Flack (1983), 1748 Friedel pairs'
_refine_ls_abs_structure_Flack   0.04(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3675
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.061
_refine_ls_R_factor_gt           0.050
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0104P)²+1.4032P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.099
_refine_ls_wR_factor_ref         0.108
_reflns_number_gt                3287
_reflns_number_total             3675
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2637.cif
_cod_data_source_block           I
_cod_database_code               2225274
_cod_database_fobs_code          2225274
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.81560(6) 0.77053(6) 0.68924(12) 0.02814(16) Uani d . 1 . .
N N1 0.68935(19) 0.86586(19) 0.6256(4) 0.0306(6) Uani d . 1 . .
N N2 0.6286(2) 0.9036(2) 0.5913(5) 0.0333(6) Uani d . 1 . .
H H2N 0.614(3) 0.927(3) 0.711(7) 0.050 Uiso d . 1 . .
N N3 0.89915(18) 0.63239(18) 0.6731(4) 0.0297(6) Uani d . 1 . .
N N4 0.9375(2) 0.5714(2) 0.6555(5) 0.0361(6) Uani d . 1 . .
H H4N 0.963(3) 0.563(3) 0.782(7) 0.054 Uiso d . 1 . .
C C1 0.8031(2) 0.8521(2) 0.8654(5) 0.0300(7) Uani d . 1 . .
C C2 0.8520(2) 0.8645(3) 1.0644(5) 0.0346(7) Uani d . 1 . .
H H2 0.8543 0.9071 1.1812 0.041 Uiso calc R 1 . .
C C3 0.8988(2) 0.8076(3) 1.0785(5) 0.0351(7) Uani d . 1 . .
H H3 0.9360 0.8081 1.2055 0.042 Uiso calc R 1 . .
C C4 0.8851(2) 0.7513(2) 0.8902(5) 0.0268(6) Uani d . 1 . .
C C5 0.7407(2) 0.8917(2) 0.8070(5) 0.0299(6) Uani d . 1 . .
H H5 0.7374 0.9380 0.9049 0.036 Uiso calc R 1 . .
C C6 0.5620(2) 0.8678(2) 0.4142(5) 0.0331(7) Uani d . 1 . .
C C7 0.4833(3) 0.8868(3) 0.4091(6) 0.0389(8) Uani d . 1 . .
H H7 0.4741 0.9214 0.5294 0.047 Uiso calc R 1 . .
C C8 0.4193(3) 0.8546(3) 0.2278(6) 0.0471(9) Uani d . 1 . .
H H8 0.3660 0.8675 0.2242 0.056 Uiso calc R 1 . .
C C9 0.4316(3) 0.8040(3) 0.0517(6) 0.0488(10) Uani d . 1 . .
H H9 0.3871 0.7823 -0.0720 0.059 Uiso calc R 1 . .
C C10 0.5088(3) 0.7852(3) 0.0562(6) 0.0431(8) Uani d . 1 . .
H H10 0.5171 0.7502 -0.0647 0.052 Uiso calc R 1 . .
C C11 0.5747(3) 0.8169(2) 0.2359(5) 0.0360(7) Uani d . 1 . .
H H11 0.6279 0.8040 0.2374 0.043 Uiso calc R 1 . .
C C12 0.9187(2) 0.6824(2) 0.8568(5) 0.0299(6) Uani d . 1 . .
H H12 0.9559 0.6736 0.9714 0.036 Uiso calc R 1 . .
C C13 0.9022(3) 0.4977(2) 0.4896(5) 0.0345(7) Uani d . 1 . .
C C14 0.8457(3) 0.4988(2) 0.3078(5) 0.0370(7) Uani d . 1 . .
H H14 0.8257 0.5468 0.2990 0.044 Uiso calc R 1 . .
C C15 0.8196(3) 0.4278(3) 0.1403(6) 0.0474(9) Uani d . 1 . .
H H15 0.7811 0.4276 0.0162 0.057 Uiso calc R 1 . .
C C16 0.8481(3) 0.3579(3) 0.1506(7) 0.0533(11) Uani d . 1 . .
H H16 0.8311 0.3110 0.0328 0.064 Uiso calc R 1 . .
C C17 0.9020(3) 0.3566(3) 0.3340(7) 0.0532(11) Uani d . 1 . .
H H17 0.9202 0.3072 0.3437 0.064 Uiso calc R 1 . .
C C18 0.9296(3) 0.4258(2) 0.5029(6) 0.0418(8) Uani d . 1 . .
H H18 0.9671 0.4246 0.6275 0.050 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 S1 C1 . . 91.41(15) ?
C5 N1 N2 . . 116.9(3) ?
N1 N2 C6 . . 119.0(3) ?
N1 N2 H2N . . 116(3) ?
C6 N2 H2N . . 119(3) ?
C12 N3 N4 . . 115.9(3) ?
N3 N4 C13 . . 120.0(3) ?
N3 N4 H4N . . 115(3) ?
C13 N4 H4N . . 119(3) ?
C2 C1 C5 . . 126.9(3) ?
C2 C1 S1 . . 111.3(2) ?
C5 C1 S1 . . 121.6(2) ?
C1 C2 C3 . . 113.1(3) ?
C1 C2 H2 . . 123.5 ?
C3 C2 H2 . . 123.5 ?
C4 C3 C2 . . 113.2(3) ?
C4 C3 H3 . . 123.4 ?
C2 C3 H3 . . 123.4 ?
C3 C4 C12 . . 126.7(3) ?
C3 C4 S1 . . 111.0(2) ?
C12 C4 S1 . . 122.2(2) ?
N1 C5 C1 . . 121.4(3) ?
N1 C5 H5 . . 119.3 ?
C1 C5 H5 . . 119.3 ?
N2 C6 C11 . . 120.8(3) ?
N2 C6 C7 . . 119.5(3) ?
C11 C6 C7 . . 119.6(3) ?
C8 C7 C6 . . 119.5(4) ?
C8 C7 H7 . . 120.2 ?
C6 C7 H7 . . 120.2 ?
C7 C8 C9 . . 120.9(4) ?
C7 C8 H8 . . 119.6 ?
C9 C8 H8 . . 119.6 ?
C10 C9 C8 . . 119.8(3) ?
C10 C9 H9 . . 120.1 ?
C8 C9 H9 . . 120.1 ?
C9 C10 C11 . . 120.7(4) ?
C9 C10 H10 . . 119.6 ?
C11 C10 H10 . . 119.6 ?
C10 C11 C6 . . 119.6(3) ?
C10 C11 H11 . . 120.2 ?
C6 C11 H11 . . 120.2 ?
N3 C12 C4 . . 120.7(3) ?
N3 C12 H12 . . 119.6 ?
C4 C12 H12 . . 119.6 ?
C18 C13 C14 . . 120.3(3) ?
C18 C13 N4 . . 118.1(3) ?
C14 C13 N4 . . 121.5(3) ?
C15 C14 C13 . . 118.4(3) ?
C15 C14 H14 . . 120.8 ?
C13 C14 H14 . . 120.8 ?
C16 C15 C14 . . 121.4(4) ?
C16 C15 H15 . . 119.3 ?
C14 C15 H15 . . 119.3 ?
C15 C16 C17 . . 119.3(4) ?
C15 C16 H16 . . 120.3 ?
C17 C16 H16 . . 120.3 ?
C18 C17 C16 . . 121.0(4) ?
C18 C17 H17 . . 119.5 ?
C16 C17 H17 . . 119.5 ?
C17 C18 C13 . . 119.5(4) ?
C17 C18 H18 . . 120.3 ?
C13 C18 H18 . . 120.3 ?
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
S1 C4 . 1.738(3) ?
S1 C1 . 1.736(3) ?
N1 C5 . 1.282(4) ?
N1 N2 . 1.361(4) ?
N2 C6 . 1.386(4) ?
N2 H2N . 0.88(4) ?
N3 C12 . 1.287(4) ?
N3 N4 . 1.362(4) ?
N4 C13 . 1.402(4) ?
N4 H4N . 0.89(4) ?
C1 C2 . 1.368(4) ?
C1 C5 . 1.436(4) ?
C2 C3 . 1.410(5) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.371(4) ?
C3 H3 . 0.9500 ?
C4 C12 . 1.431(4) ?
C5 H5 . 0.9500 ?
C6 C11 . 1.396(5) ?
C6 C7 . 1.405(5) ?
C7 C8 . 1.382(5) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.382(6) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.379(5) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.391(5) ?
C10 H10 . 0.9500 ?
C11 H11 . 0.9500 ?
C12 H12 . 0.9500 ?
C13 C18 . 1.392(5) ?
C13 C14 . 1.400(5) ?
C14 C15 . 1.391(5) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.374(6) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.383(6) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.377(5) ?
C17 H17 . 0.9500 ?
C18 H18 . 0.9500 ?
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 H2n N4 3_675 0.88(4) 2.58(5) 3.398(4) 155(4)
C12 H12 N2 2_765 0.95 2.57 3.463(5) 157
N4 H4N Cg 2_765 0.89(4) 2.81(5) 3.415(4) 126(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 N2 C6 . . . . -171.4(3) ?
C12 N3 N4 C13 . . . . 165.1(3) ?
C4 S1 C1 C2 . . . . 1.3(3) ?
C4 S1 C1 C5 . . . . -173.5(3) ?
C5 C1 C2 C3 . . . . 173.6(3) ?
S1 C1 C2 C3 . . . . -0.9(4) ?
C1 C2 C3 C4 . . . . -0.3(4) ?
C2 C3 C4 C12 . . . . -176.8(3) ?
C2 C3 C4 S1 . . . . 1.3(4) ?
C1 S1 C4 C3 . . . . -1.5(3) ?
C1 S1 C4 C12 . . . . 176.7(3) ?
N2 N1 C5 C1 . . . . 176.6(3) ?
C2 C1 C5 N1 . . . . -171.7(3) ?
S1 C1 C5 N1 . . . . 2.2(4) ?
N1 N2 C6 C11 . . . . -18.7(4) ?
N1 N2 C6 C7 . . . . 164.1(3) ?
N2 C6 C7 C8 . . . . 177.3(3) ?
C11 C6 C7 C8 . . . . 0.1(5) ?
C6 C7 C8 C9 . . . . 0.0(5) ?
C7 C8 C9 C10 . . . . 0.0(5) ?
C8 C9 C10 C11 . . . . -0.2(5) ?
C9 C10 C11 C6 . . . . 0.4(5) ?
N2 C6 C11 C10 . . . . -177.5(3) ?
C7 C6 C11 C10 . . . . -0.3(5) ?
N4 N3 C12 C4 . . . . 177.9(3) ?
C3 C4 C12 N3 . . . . 178.5(3) ?
S1 C4 C12 N3 . . . . 0.7(4) ?
N3 N4 C13 C18 . . . . -168.3(3) ?
N3 N4 C13 C14 . . . . 15.3(5) ?
C18 C13 C14 C15 . . . . -1.2(5) ?
N4 C13 C14 C15 . . . . 175.2(3) ?
C13 C14 C15 C16 . . . . -0.1(6) ?
C14 C15 C16 C17 . . . . 1.6(6) ?
C15 C16 C17 C18 . . . . -1.8(7) ?
C16 C17 C18 C13 . . . . 0.5(6) ?
C14 C13 C18 C17 . . . . 1.0(5) ?
N4 C13 C18 C17 . . . . -175.5(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744395
