#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/43/2014335.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_2014335
loop_
_publ_author_name
'Leji Latheef'
'E. Manoj'
'M. R. Prathapachandra Kurup'
_publ_section_title
;
 Salicylaldehyde 4,4'-(hexane-1,6-diyl)thiosemicarbazone
;
_journal_coeditor_code           GA1110
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o16
_journal_page_last               o18
_journal_paper_doi               10.1107/S010827010503564X
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C14 H19 N3 O S'
_chemical_formula_moiety         'C14 H19 N3 O S'
_chemical_formula_sum            'C14 H19 N3 O S'
_chemical_formula_weight         277.38
_chemical_name_systematic
;
Salicylaldehyde 4,4'-(hexane-1,6-diyl)thiosemicarbazone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.617(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.4480(11)
_cell_length_b                   14.099(2)
_cell_length_c                   15.924(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      10.3600
_cell_measurement_theta_min      5.1100
_cell_volume                     1443.0(4)
_computing_cell_refinement       Argus-MACH3
_computing_data_collection       'Argus-MACH3 (Nonius, 1997)'
_computing_data_reduction        'Maxus (Mackay et al.,  1998)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Nonius MACH3'
_diffrn_measurement_method       ω/θ
_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  0.0203
_diffrn_reflns_av_sigmaI/netI    0.0746
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2764
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         1.93
_diffrn_standards_decay_%        <3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.162
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.1402
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0454P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.1102
_reflns_number_gt                1290
_reflns_number_total             2524
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ga1110.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2014335
_cod_database_fobs_code          2014335
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.21929(11) 0.56737(6) 0.10776(5) 0.0770(3) Uani d . 1 . . S
O1 0.3863(3) 0.33725(19) 0.18426(15) 0.0889(7) Uani d . 1 . . O
N1 0.4799(3) 0.69895(16) 0.05486(13) 0.0583(6) Uani d . 1 . . N
N2 0.6187(4) 0.55296(17) 0.08523(15) 0.0595(7) Uani d . 1 . . N
N3 0.6053(3) 0.46472(16) 0.11829(13) 0.0570(6) Uani d . 1 . . N
C1 0.7457(4) 0.31658(19) 0.15758(16) 0.0556(7) Uani d . 1 . . C
C2 0.5586(5) 0.2834(2) 0.18579(17) 0.0648(8) Uani d . 1 . . C
C3 0.5480(6) 0.1925(3) 0.2169(2) 0.0881(10) Uani d . 1 . . C
H3 0.4237 0.1705 0.2355 0.106 Uiso calc R 1 . . H
C4 0.7150(7) 0.1352(3) 0.22059(19) 0.0916(11) Uani d . 1 . . C
H4 0.7040 0.0741 0.2419 0.110 Uiso calc R 1 . . H
C5 0.9023(6) 0.1649(2) 0.1936(2) 0.0914(10) Uani d . 1 . . C
H5 1.0168 0.1246 0.1961 0.110 Uiso calc R 1 . . H
C6 0.9152(5) 0.2559(2) 0.16264(17) 0.0712(8) Uani d . 1 . . C
H6 1.0410 0.2770 0.1447 0.085 Uiso calc R 1 . . H
C7 0.4484(4) 0.6105(2) 0.08094(15) 0.0565(7) Uani d . 1 . . C
C8 0.7626(4) 0.41038(19) 0.12273(15) 0.0573(7) Uani d . 1 . . C
H8 0.8877 0.4309 0.1037 0.069 Uiso calc R 1 . . H
C9 0.3082(4) 0.76605(19) 0.04709(18) 0.0713(8) Uani d . 1 . . C
H9A 0.1781 0.7312 0.0432 0.086 Uiso calc R 1 . . H
H9B 0.3147 0.8017 -0.0047 0.086 Uiso calc R 1 . . H
C10 0.3098(5) 0.8346(2) 0.12009(19) 0.0801(9) Uani d . 1 . . C
H10A 0.1692 0.8572 0.1247 0.096 Uiso calc R 1 . . H
H10B 0.3527 0.8007 0.1716 0.096 Uiso calc R 1 . . H
C11 0.4501(5) 0.9184(2) 0.1129(2) 0.0912(10) Uani d . 1 . . C
H11A 0.4447 0.9569 0.1632 0.109 Uiso calc R 1 . . H
H11B 0.3963 0.9565 0.0653 0.109 Uiso calc R 1 . . H
C12 0.6746(5) 0.8952(2) 0.1019(2) 0.0900(10) Uani d . 1 . . C
H12A 0.7318 0.8619 0.1518 0.108 Uiso calc R 1 . . H
H12B 0.7508 0.9542 0.0985 0.108 Uiso calc R 1 . . H
C13 0.7128(4) 0.83558(19) 0.02532(18) 0.0752(9) Uani d . 1 . . C
H13A 0.6169 0.8560 -0.0213 0.090 Uiso calc R 1 . . H
H13B 0.8526 0.8482 0.0099 0.090 Uiso calc R 1 . . H
C14 0.6889(4) 0.73076(18) 0.03630(18) 0.0664(8) Uani d . 1 . . C
H14A 0.7251 0.6995 -0.0148 0.080 Uiso calc R 1 . . H
H14B 0.7878 0.7101 0.0817 0.080 Uiso calc R 1 . . H
H2N 0.721(3) 0.5682(15) 0.0652(14) 0.039(8) Uiso d . 1 . . H
H1O1 0.413(5) 0.396(2) 0.162(2) 0.125(14) Uiso d . 1 . . H
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'
O O 0.0106 0.0060 '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
_geom_angle_publ_flag
C2 O1 H1O1 110(2) ?
C7 N1 C9 120.0(2) ?
C7 N1 C14 120.8(2) ?
C9 N1 C14 119.2(2) ?
N3 N2 C7 119.3(3) y
N3 N2 H2N 119.4(17) ?
C7 N2 H2N 121.1(17) ?
C8 N3 N2 120.0(2) y
C6 C1 C2 118.1(3) ?
C6 C1 C8 120.4(3) ?
C2 C1 C8 121.5(3) ?
O1 C2 C3 117.8(3) y
O1 C2 C1 122.5(3) y
C3 C2 C1 119.6(3) y
C4 C3 C2 120.9(3) ?
C4 C3 H3 119.6 ?
C2 C3 H3 119.6 ?
C3 C4 C5 121.5(3) ?
C3 C4 H4 119.3 ?
C5 C4 H4 119.3 ?
C6 C5 C4 118.3(3) ?
C6 C5 H5 120.9 ?
C4 C5 H5 120.9 ?
C5 C6 C1 121.7(3) ?
C5 C6 H6 119.2 ?
C1 C6 H6 119.2 ?
N1 C7 N2 115.4(2) y
N1 C7 S1 125.0(2) y
N2 C7 S1 119.5(2) y
N3 C8 C1 119.4(2) y
N3 C8 H8 120.3 ?
C1 C8 H8 120.3 ?
N1 C9 C10 113.1(2) ?
N1 C9 H9A 109.0 ?
C10 C9 H9A 109.0 ?
N1 C9 H9B 109.0 ?
C10 C9 H9B 109.0 ?
H9A C9 H9B 107.8 ?
C11 C10 C9 114.4(3) ?
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 115.4(3) ?
C10 C11 H11A 108.4 ?
C12 C11 H11A 108.4 ?
C10 C11 H11B 108.4 ?
C12 C11 H11B 108.4 ?
H11A C11 H11B 107.5 ?
C11 C12 C13 115.7(3) ?
C11 C12 H12A 108.4 ?
C13 C12 H12A 108.4 ?
C11 C12 H12B 108.4 ?
C13 C12 H12B 108.4 ?
H12A C12 H12B 107.4 ?
C14 C13 C12 115.3(2) ?
C14 C13 H13A 108.4 ?
C12 C13 H13A 108.4 ?
C14 C13 H13B 108.4 ?
C12 C13 H13B 108.4 ?
H13A C13 H13B 107.5 ?
N1 C14 C13 115.4(2) ?
N1 C14 H14A 108.4 ?
C13 C14 H14A 108.4 ?
N1 C14 H14B 108.4 ?
C13 C14 H14B 108.4 ?
H14A C14 H14B 107.5 ?
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 C7 . 1.684(3) y
O1 C2 . 1.344(3) ?
O1 H1O1 . 0.92(3) ?
N1 C7 . 1.336(3) y
N1 C9 . 1.454(3) ?
N1 C14 . 1.472(3) ?
N2 N3 . 1.356(3) y
N2 C7 . 1.362(3) y
N2 H2N . 0.78(2) ?
N3 C8 . 1.269(3) y
C1 C6 . 1.386(4) ?
C1 C2 . 1.401(4) ?
C1 C8 . 1.442(3) ?
C2 C3 . 1.378(4) ?
C3 C4 . 1.344(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.379(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.379(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C8 H8 . 0.9300 ?
C9 C10 . 1.511(3) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.498(4) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.508(4) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.517(4) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.497(3) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
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
_geom_hbond_publ_flag
O1 H1O1 N3 1_555 0.92(3) 1.76(3) 2.562(3) 144(3) yes
O1 H1O1 S1 1_555 0.92(3) 2.82(3) 3.600(3) 143(3) yes
C6 H6 O1 1_655 0.93 2.42 3.239(4) 147 yes
C8 H8 S1 1_655 0.93 2.87 3.706(6) 150 yes
C9 H9B Cg1 3_665 0.97 2.96 3.7580(10) 141 yes
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
C7 N2 N3 C8 -180.0(2)
C6 C1 C2 O1 179.3(3)
C8 C1 C2 O1 -1.8(4)
C6 C1 C2 C3 -0.4(4)
C8 C1 C2 C3 178.5(3)
O1 C2 C3 C4 -179.6(3)
C1 C2 C3 C4 0.1(5)
C2 C3 C4 C5 0.0(5)
C3 C4 C5 C6 0.3(5)
C4 C5 C6 C1 -0.7(4)
C2 C1 C6 C5 0.7(4)
C8 C1 C6 C5 -178.2(3)
C9 N1 C7 N2 179.4(2)
C14 N1 C7 N2 -2.6(3)
C9 N1 C7 S1 -0.6(3)
C14 N1 C7 S1 177.40(18)
N3 N2 C7 N1 174.1(2)
N3 N2 C7 S1 -6.0(3)
N2 N3 C8 C1 -179.7(2)
C6 C1 C8 N3 179.7(2)
C2 C1 C8 N3 0.8(4)
C7 N1 C9 C10 101.1(3)
C14 N1 C9 C10 -76.9(3)
N1 C9 C10 C11 83.0(3)
C9 C10 C11 C12 -56.2(4)
C10 C11 C12 C13 58.7(4)
C11 C12 C13 C14 -83.4(3)
C7 N1 C14 C13 -167.7(2)
C9 N1 C14 C13 10.3(3)
C12 C13 C14 N1 61.8(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21180986
