#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/36/2013614.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_2013614
loop_
_publ_author_name
'Bernhardt, Paul V.'
'Caldwell, Lorraine M.'
'Lovejoy, David B.'
'Richardson, Des R.'
_publ_section_title
;
 Four cytotoxic N4-substituted thiosemicarbazones derived from
 2-hydroxynaphthalene-1-carboxaldehyde
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o629
_journal_page_last               o633
_journal_paper_doi               10.1107/S0108270103021401
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C18 H15 N3 O S'
_chemical_formula_moiety         'C18 H15 N3 O S'
_chemical_formula_structural     'C18 H15 N3 O S'
_chemical_formula_sum            'C18 H15 N3 O S'
_chemical_formula_weight         321.39
_chemical_name_systematic
;
1-[(4-phenylthiosemicarbazono)methyl]-2-naphthol
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.1
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 95.480(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.243(4)
_cell_length_b                   6.7948(6)
_cell_length_c                   24.471(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      14.34
_cell_measurement_theta_min      9.65
_cell_volume                     3185.0(11)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLUTON (Spek, 1990)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf-Nonius TurboCAD-4'
_diffrn_measurement_method       'non-profiled ω/2θ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.014
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            2834
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         1.67
_diffrn_standards_decay_%        -5
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.911
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.34
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2747
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.108
_refine_ls_R_factor_gt           0.040
_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)+(0.0576P)²+0.9608P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.099
_refine_ls_wR_factor_ref         0.126
_reflns_number_gt                1425
_reflns_number_total             2747
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg1180.cif
_cod_data_source_block           V
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2013614
_cod_database_fobs_code          2013614
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
C1 0.48619(11) 0.2486(4) 0.01483(9) 0.0419(6) Uani d . 1 . . C
C2 0.43538(13) 0.2363(4) -0.02902(10) 0.0501(6) Uani d . 1 . . C
C3 0.36460(13) 0.2115(4) -0.02146(11) 0.0619(8) Uani d . 1 . . C
H3 0.3314 0.2053 -0.0517 0.074 Uiso calc R 1 . . H
C4 0.34470(13) 0.1965(4) 0.03009(12) 0.0626(8) Uani d . 1 . . C
H4 0.2979 0.1757 0.0347 0.075 Uiso calc R 1 . . H
C5 0.39304(13) 0.2115(4) 0.07659(10) 0.0505(7) Uani d . 1 . . C
C6 0.37140(15) 0.1996(4) 0.13032(12) 0.0639(8) Uani d . 1 . . C
H6 0.3246 0.1771 0.1348 0.077 Uiso calc R 1 . . H
C7 0.41766(18) 0.2204(5) 0.17500(12) 0.0751(10) Uani d . 1 . . C
H7 0.4026 0.2137 0.21 0.09 Uiso calc R 1 . . H
C8 0.48783(17) 0.2518(5) 0.16862(11) 0.0763(9) Uani d . 1 . . C
H8 0.5194 0.2668 0.1996 0.092 Uiso calc R 1 . . H
C9 0.51119(15) 0.2611(4) 0.11772(10) 0.0626(8) Uani d . 1 . . C
H9 0.5584 0.2815 0.1146 0.075 Uiso calc R 1 . . H
C10 0.46500(12) 0.2402(4) 0.06970(9) 0.0469(6) Uani d . 1 . . C
C11 0.55942(12) 0.2633(4) 0.00645(9) 0.0461(6) Uani d . 1 . . C
H11 0.592 0.2639 0.037 0.055 Uiso calc R 1 . . H
C12 0.68278(12) 0.2865(4) -0.09027(10) 0.0502(7) Uani d . 1 . . C
C13 0.65146(13) 0.3281(4) -0.19175(10) 0.0520(7) Uani d . 1 . . C
C14 0.70859(15) 0.4233(5) -0.20872(11) 0.0662(8) Uani d . 1 . . C
H14 0.7426 0.4755 -0.1832 0.079 Uiso calc R 1 . . H
C15 0.71459(18) 0.4402(5) -0.26474(13) 0.0759(9) Uani d . 1 . . C
H15 0.7533 0.5032 -0.2767 0.091 Uiso calc R 1 . . H
C17 0.60859(17) 0.2716(5) -0.28513(12) 0.0856(11) Uani d . 1 . . C
H17 0.5749 0.2188 -0.3107 0.103 Uiso calc R 1 . . H
C18 0.60151(14) 0.2537(5) -0.22952(11) 0.0682(8) Uani d . 1 . . C
H18 0.5626 0.1909 -0.2179 0.082 Uiso calc R 1 . . H
C16 0.66484(19) 0.3663(6) -0.30226(13) 0.0841(11) Uani d . 1 . . C
H16 0.6692 0.3804 -0.3396 0.101 Uiso calc R 1 . . H
N1 0.58142(10) 0.2756(3) -0.04149(8) 0.0464(5) Uani d . 1 . . N
N2 0.65255(11) 0.2785(4) -0.04284(9) 0.0527(6) Uani d . 1 . . N
N3 0.63899(12) 0.3115(4) -0.13526(8) 0.0552(7) Uani d . 1 . . N
O1 0.45075(11) 0.2448(4) -0.08171(7) 0.0691(6) Uani d . 1 . . O
S1 0.76909(3) 0.25906(17) -0.08846(3) 0.0886(4) Uani d . 1 . . S
H1A 0.4938(17) 0.258(5) -0.0812(12) 0.086(11) Uiso d . 1 . . H
H2A 0.6754(15) 0.274(4) -0.0133(12) 0.076(10) Uiso d . 1 . . H
H3A 0.5987(15) 0.312(4) -0.1284(11) 0.070(10) 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 0 '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 0.006 '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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-9 -1 9
2 -4 2
-3 -3 2
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 C1 C10 118.6(2) ?
C2 C1 C11 121.3(2) ?
C10 C1 C11 120.1(2) ?
O1 C2 C1 122.3(2) ?
O1 C2 C3 115.8(2) ?
C1 C2 C3 121.9(2) ?
C4 C3 C2 119.7(2) ?
C4 C3 H3 120.1 ?
C2 C3 H3 120.1 ?
C3 C4 C5 121.6(2) ?
C3 C4 H4 119.2 ?
C5 C4 H4 119.2 ?
C4 C5 C6 121.1(2) ?
C4 C5 C10 119.4(2) ?
C6 C5 C10 119.5(2) ?
C7 C6 C5 121.0(3) ?
C7 C6 H6 119.5 ?
C5 C6 H6 119.5 ?
C6 C7 C8 119.9(3) ?
C6 C7 H7 120.1 ?
C8 C7 H7 120.1 ?
C9 C8 C7 121.1(3) ?
C9 C8 H8 119.4 ?
C7 C8 H8 119.4 ?
C8 C9 C10 121.3(3) ?
C8 C9 H9 119.4 ?
C10 C9 H9 119.4 ?
C9 C10 C5 117.2(2) ?
C9 C10 C1 124.1(2) ?
C5 C10 C1 118.7(2) ?
N1 C11 C1 122.9(2) yes
N1 C11 H11 118.6 ?
C1 C11 H11 118.6 ?
N3 C12 N2 115.2(2) yes
N3 C12 S1 125.88(19) ?
N2 C12 S1 118.89(19) ?
C18 C13 C14 120.1(2) ?
C18 C13 N3 116.9(2) ?
C14 C13 N3 122.8(2) ?
C13 C14 C15 118.7(3) ?
C13 C14 H14 120.6 ?
C15 C14 H14 120.6 ?
C16 C15 C14 121.1(3) ?
C16 C15 H15 119.5 ?
C14 C15 H15 119.5 ?
C16 C17 C18 120.0(3) ?
C16 C17 H17 120.0 ?
C18 C17 H17 120.0 ?
C13 C18 C17 120.2(3) ?
C13 C18 H18 119.9 ?
C17 C18 H18 119.9 ?
C15 C16 C17 119.8(3) ?
C15 C16 H16 120.1 ?
C17 C16 H16 120.1 ?
C11 N1 N2 116.0(2) yes
C12 N2 N1 122.3(2) yes
C12 N2 H2A 122(2) ?
N1 N2 H2A 116(2) ?
C12 N3 C13 131.1(2) yes
C12 N3 H3A 112(2) ?
C13 N3 H3A 117(2) ?
C2 O1 H1A 107(2) ?
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
C1 C2 . 1.384(3) ?
C1 C10 . 1.441(3) ?
C1 C11 . 1.447(3) ?
C2 O1 . 1.351(3) yes
C2 C3 . 1.402(3) ?
C3 C4 . 1.357(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.403(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.419(3) ?
C5 C10 . 1.424(3) ?
C6 C7 . 1.350(4) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.390(4) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.366(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.411(3) ?
C9 H9 . 0.9300 ?
C11 N1 . 1.288(3) ?
C11 H11 . 0.9300 ?
C12 N3 . 1.332(3) yes
C12 N2 . 1.348(3) yes
C12 S1 . 1.668(2) yes
C13 C18 . 1.365(4) ?
C13 C14 . 1.374(4) ?
C13 N3 . 1.430(3) yes
C14 C15 . 1.391(4) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.358(4) ?
C15 H15 . 0.9300 ?
C17 C16 . 1.359(4) ?
C17 C18 . 1.386(4) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
C16 H16 . 0.9300 ?
N1 N2 . 1.372(3) yes
N2 H2A . 0.81(3) ?
N3 H3A . 0.81(3) ?
O1 H1A . 0.83(3) ?
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
O1 H1A N1 . 0.83(4) 1.86(4) 2.620(3) 150(3)
N3 H3A N1 . 0.81(3) 2.20(3) 2.653(3) 116(3)
N2 H2A S1 7_655 0.82(3) 2.62(3) 3.425(3) 171(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
C10 C1 C2 O1 179.4(3)
C11 C1 C2 O1 -2.6(4)
C10 C1 C2 C3 -1.5(4)
C11 C1 C2 C3 176.5(3)
O1 C2 C3 C4 178.4(3)
C1 C2 C3 C4 -0.8(4)
C2 C3 C4 C5 2.1(5)
C3 C4 C5 C6 178.7(3)
C3 C4 C5 C10 -1.0(4)
C4 C5 C6 C7 -177.9(3)
C10 C5 C6 C7 1.8(4)
C5 C6 C7 C8 -0.7(5)
C6 C7 C8 C9 -0.4(5)
C7 C8 C9 C10 0.4(5)
C8 C9 C10 C5 0.7(4)
C8 C9 C10 C1 179.9(3)
C4 C5 C10 C9 177.9(3)
C6 C5 C10 C9 -1.8(4)
C4 C5 C10 C1 -1.3(4)
C6 C5 C10 C1 179.0(2)
C2 C1 C10 C9 -176.7(3)
C11 C1 C10 C9 5.3(4)
C2 C1 C10 C5 2.5(4)
C11 C1 C10 C5 -175.5(2)
C2 C1 C11 N1 3.5(4)
C10 C1 C11 N1 -178.5(2)
C18 C13 C14 C15 -0.6(5)
N3 C13 C14 C15 -176.9(3)
C13 C14 C15 C16 0.7(5)
C14 C13 C18 C17 0.8(5)
N3 C13 C18 C17 177.4(3)
C16 C17 C18 C13 -1.1(5)
C14 C15 C16 C17 -0.9(6)
C18 C17 C16 C15 1.1(6)
C1 C11 N1 N2 -176.8(2)
N3 C12 N2 N1 6.5(4)
S1 C12 N2 N1 -171.86(19)
C11 N1 N2 C12 178.5(3)
N2 C12 N3 C13 179.5(3)
S1 C12 N3 C13 -2.3(5)
C18 C13 N3 C12 147.0(3)
C14 C13 N3 C12 -36.5(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652377
