#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/46/2224618.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_2224618
loop_
_publ_author_name
'Islam, M. A. A. A. A.'
'Tarafder, M. T. H.'
'Zakaria, C. M.'
'Guidolin, N.'
'Zangrando, E.'
_publ_section_title
;
 (E)-4-Octyloxybenzaldehyde thiosemicarbazone
;
_journal_coeditor_code           FJ2264
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o241
_journal_paper_doi               10.1107/S1600536809054841
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H25 N3 O S'
_chemical_formula_moiety         'C16 H25 N3 O S'
_chemical_formula_sum            'C16 H25 N3 O S'
_chemical_formula_weight         307.45
_chemical_name_systematic
;
(E)-4-Octyloxybenzaldehyde thiosemicarbazone
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.74(2)
_cell_angle_beta                 91.85(2)
_cell_angle_gamma                104.42(3)
_cell_formula_units_Z            2
_cell_length_a                   5.785(2)
_cell_length_b                   7.586(2)
_cell_length_c                   20.789(4)
_cell_measurement_reflns_used    146
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.1
_cell_measurement_theta_min      3.0
_cell_volume                     879.2(4)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'XPRESS (MacScience, 2002)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELX97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELX97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type
'Enraf--Nonius dip1030 image-plate diffractometer'
_diffrn_measurement_method       'φ-scans with narrow frames'
_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  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9930
_diffrn_reflns_theta_full        25.67
_diffrn_reflns_theta_max         25.67
_diffrn_reflns_theta_min         3.64
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.161
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.183
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3226
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1026P)²+0.0242P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1351
_refine_ls_wR_factor_ref         0.1398
_reflns_number_gt                2749
_reflns_number_total             3226
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            fj2264.cif
_cod_data_source_block           I
_cod_database_code               2224618
_cod_database_fobs_code          2224618
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 1.33919(6) -0.29398(5) 0.99374(2) 0.06930(19) Uani d . 1 . .
N N1 1.0386(2) 0.02579(17) 0.89975(6) 0.0648(3) Uani d . 1 . .
N N2 1.1983(2) -0.04336(17) 0.93483(6) 0.0690(3) Uani d . 1 . .
H H2 1.3435 0.0203 0.9421 0.083 Uiso calc R 1 . .
N N3 0.9025(2) -0.29670(17) 0.94909(6) 0.0668(3) Uani d . 1 . .
H H3A 0.8033 -0.2489 0.9295 0.080 Uiso calc R 1 . .
H H3B 0.8534 -0.4024 0.9631 0.080 Uiso calc R 1 . .
O O1 0.6110(2) 0.55328(16) 0.73145(6) 0.0812(3) Uani d . 1 . .
C C1 1.1305(2) -0.20768(19) 0.95761(7) 0.0591(3) Uani d . 1 . .
C C2 1.1216(3) 0.1882(2) 0.88465(7) 0.0663(4) Uani d . 1 . .
H H2A 1.2764 0.2498 0.8995 0.080 Uiso calc R 1 . .
C C3 0.9864(3) 0.2818(2) 0.84546(7) 0.0630(4) Uani d . 1 . .
C C4 0.7501(3) 0.2031(2) 0.82202(7) 0.0681(4) Uani d . 1 . .
H H4 0.6725 0.0867 0.8321 0.082 Uiso calc R 1 . .
C C5 0.6322(3) 0.2971(2) 0.78409(8) 0.0716(4) Uani d . 1 . .
H H5 0.4761 0.2431 0.7683 0.086 Uiso calc R 1 . .
C C6 0.7444(3) 0.4721(2) 0.76919(7) 0.0677(4) Uani d . 1 . .
C C7 0.9777(3) 0.5528(2) 0.79263(7) 0.0726(4) Uani d . 1 . .
H H7 1.0536 0.6704 0.7833 0.087 Uiso calc R 1 . .
C C8 1.0957(3) 0.4563(2) 0.82997(7) 0.0698(4) Uani d . 1 . .
H H8 1.2526 0.5100 0.8451 0.084 Uiso calc R 1 . .
C C9 0.7089(4) 0.7404(2) 0.72041(9) 0.0880(5) Uani d . 1 . .
H H9A 0.8564 0.7529 0.6983 0.106 Uiso calc R 1 . .
H H9B 0.7432 0.8161 0.7612 0.106 Uiso calc R 1 . .
C C10 0.5257(4) 0.7986(3) 0.67937(9) 0.0890(5) Uani d . 1 . .
H H10A 0.3717 0.7624 0.6982 0.107 Uiso calc R 1 . .
H H10B 0.5693 0.9309 0.6805 0.107 Uiso calc R 1 . .
C C11 0.5012(4) 0.7192(3) 0.60985(8) 0.0811(5) Uani d . 1 . .
H H11A 0.4523 0.5869 0.6085 0.097 Uiso calc R 1 . .
H H11B 0.6561 0.7522 0.5913 0.097 Uiso calc R 1 . .
C C12 0.3221(3) 0.7838(3) 0.56889(9) 0.0817(5) Uani d . 1 . .
H H12A 0.1660 0.7448 0.5863 0.098 Uiso calc R 1 . .
H H12B 0.3662 0.9164 0.5727 0.098 Uiso calc R 1 . .
C C13 0.3025(3) 0.7155(2) 0.49799(9) 0.0826(5) Uani d . 1 . .
H H13A 0.2573 0.5828 0.4940 0.099 Uiso calc R 1 . .
H H13B 0.4583 0.7543 0.4803 0.099 Uiso calc R 1 . .
C C14 0.1228(3) 0.7824(3) 0.45814(8) 0.0810(5) Uani d . 1 . .
H H14A -0.0331 0.7420 0.4756 0.097 Uiso calc R 1 . .
H H14B 0.1667 0.9150 0.4629 0.097 Uiso calc R 1 . .
C C15 0.1029(4) 0.7182(3) 0.38689(9) 0.0891(5) Uani d . 1 . .
H H15A 0.0562 0.5857 0.3819 0.107 Uiso calc R 1 . .
H H15B 0.2589 0.7573 0.3693 0.107 Uiso calc R 1 . .
C C16 -0.0752(4) 0.7893(3) 0.34816(10) 0.0987(6) Uani d . 1 . .
H H16A -0.2329 0.7416 0.3624 0.148 Uiso calc R 1 . .
H H16B -0.0710 0.7509 0.3031 0.148 Uiso calc R 1 . .
H H16C -0.0347 0.9204 0.3544 0.148 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'
O O 0.0106 0.0060 '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
C2 N1 N2 . . 114.83(13) ?
C1 N2 N1 . . 121.23(12) ?
C1 N2 H2 . . 119.4 ?
N1 N2 H2 . . 119.4 ?
C1 N3 H3A . . 120.0 ?
C1 N3 H3B . . 120.0 ?
H3A N3 H3B . . 120.0 ?
C6 O1 C9 . . 117.89(14) ?
N3 C1 N2 . . 117.74(13) ?
N3 C1 S1 . . 123.14(12) ?
N2 C1 S1 . . 119.09(11) ?
N1 C2 C3 . . 123.26(14) ?
N1 C2 H2A . . 118.4 ?
C3 C2 H2A . . 118.4 ?
C8 C3 C4 . . 118.26(14) ?
C8 C3 C2 . . 118.79(14) ?
C4 C3 C2 . . 122.94(15) ?
C5 C4 C3 . . 120.37(15) ?
C5 C4 H4 . . 119.8 ?
C3 C4 H4 . . 119.8 ?
C4 C5 C6 . . 120.57(15) ?
C4 C5 H5 . . 119.7 ?
C6 C5 H5 . . 119.7 ?
O1 C6 C7 . . 124.47(15) ?
O1 C6 C5 . . 115.77(15) ?
C7 C6 C5 . . 119.76(15) ?
C8 C7 C6 . . 119.26(15) ?
C8 C7 H7 . . 120.4 ?
C6 C7 H7 . . 120.4 ?
C7 C8 C3 . . 121.78(15) ?
C7 C8 H8 . . 119.1 ?
C3 C8 H8 . . 119.1 ?
O1 C9 C10 . . 107.53(17) ?
O1 C9 H9A . . 110.2 ?
C10 C9 H9A . . 110.2 ?
O1 C9 H9B . . 110.2 ?
C10 C9 H9B . . 110.2 ?
H9A C9 H9B . . 108.5 ?
C11 C10 C9 . . 114.12(15) ?
C11 C10 H10A . . 108.7 ?
C9 C10 H10A . . 108.7 ?
C11 C10 H10B . . 108.7 ?
C9 C10 H10B . . 108.7 ?
H10A C10 H10B . . 107.6 ?
C10 C11 C12 . . 113.38(15) ?
C10 C11 H11A . . 108.9 ?
C12 C11 H11A . . 108.9 ?
C10 C11 H11B . . 108.9 ?
C12 C11 H11B . . 108.9 ?
H11A C11 H11B . . 107.7 ?
C13 C12 C11 . . 114.97(15) ?
C13 C12 H12A . . 108.5 ?
C11 C12 H12A . . 108.5 ?
C13 C12 H12B . . 108.5 ?
C11 C12 H12B . . 108.5 ?
H12A C12 H12B . . 107.5 ?
C12 C13 C14 . . 113.91(15) ?
C12 C13 H13A . . 108.8 ?
C14 C13 H13A . . 108.8 ?
C12 C13 H13B . . 108.8 ?
C14 C13 H13B . . 108.8 ?
H13A C13 H13B . . 107.7 ?
C15 C14 C13 . . 114.88(16) ?
C15 C14 H14A . . 108.5 ?
C13 C14 H14A . . 108.5 ?
C15 C14 H14B . . 108.5 ?
C13 C14 H14B . . 108.5 ?
H14A C14 H14B . . 107.5 ?
C14 C15 C16 . . 113.71(16) ?
C14 C15 H15A . . 108.8 ?
C16 C15 H15A . . 108.8 ?
C14 C15 H15B . . 108.8 ?
C16 C15 H15B . . 108.8 ?
H15A C15 H15B . . 107.7 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
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 C1 . 1.6930(15) ?
N1 C2 . 1.275(2) ?
N1 N2 . 1.3863(16) ?
N2 C1 . 1.341(2) ?
N2 H2 . 0.8600 ?
N3 C1 . 1.3227(19) ?
N3 H3A . 0.8600 ?
N3 H3B . 0.8600 ?
O1 C6 . 1.3665(19) ?
O1 C9 . 1.432(2) ?
C2 C3 . 1.453(2) ?
C2 H2A . 0.9300 ?
C3 C8 . 1.387(2) ?
C3 C4 . 1.402(2) ?
C4 C5 . 1.377(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.390(2) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.389(2) ?
C7 C8 . 1.383(2) ?
C7 H7 . 0.9300 ?
C8 H8 . 0.9300 ?
C9 C10 . 1.511(3) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.507(3) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.518(2) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.513(3) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.517(2) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C15 . 1.512(3) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 C16 . 1.515(3) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
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
C2 N1 N2 C1 . . . . 175.56(13) ?
N1 N2 C1 N3 . . . . -4.3(2) ?
N1 N2 C1 S1 . . . . 174.08(10) ?
N2 N1 C2 C3 . . . . 177.06(12) ?
N1 C2 C3 C8 . . . . -177.92(14) ?
N1 C2 C3 C4 . . . . 1.6(2) ?
C8 C3 C4 C5 . . . . 0.7(2) ?
C2 C3 C4 C5 . . . . -178.83(13) ?
C3 C4 C5 C6 . . . . -0.8(2) ?
C9 O1 C6 C7 . . . . -6.4(2) ?
C9 O1 C6 C5 . . . . 173.52(14) ?
C4 C5 C6 O1 . . . . -179.76(13) ?
C4 C5 C6 C7 . . . . 0.1(2) ?
O1 C6 C7 C8 . . . . -179.39(14) ?
C5 C6 C7 C8 . . . . 0.7(2) ?
C6 C7 C8 C3 . . . . -0.9(2) ?
C4 C3 C8 C7 . . . . 0.2(2) ?
C2 C3 C8 C7 . . . . 179.72(13) ?
C6 O1 C9 C10 . . . . -178.39(13) ?
O1 C9 C10 C11 . . . . -73.0(2) ?
C9 C10 C11 C12 . . . . -178.21(16) ?
C10 C11 C12 C13 . . . . 176.73(17) ?
C11 C12 C13 C14 . . . . -179.85(15) ?
C12 C13 C14 C15 . . . . 179.08(16) ?
C13 C14 C15 C16 . . . . -179.20(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7845294
