#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/36/2013616.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_2013616
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          'C13 H13 N3 O S'
_chemical_formula_moiety         'C13 H13 N3 O S'
_chemical_formula_structural     'C13 H13 N3 O S'
_chemical_formula_sum            'C13 H13 N3 O S'
_chemical_formula_weight         259.32
_chemical_name_systematic
;
1-[(4-methylthiosemicarbazono)methyl]-2-naphthol
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 91.31(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2930(10)
_cell_length_b                   5.1612(3)
_cell_length_c                   12.5630(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15.95
_cell_measurement_theta_min      10.45
_cell_volume                     602.40(9)
_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 1
_diffrn_measured_fraction_theta_max 1
_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  0.023
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            1262
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         1.62
_diffrn_standards_decay_%        -2
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.43
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.16
_refine_ls_abs_structure_details 'Bernardinelli & Flack (1985)'
_refine_ls_abs_structure_Flack   0.01(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         1185
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.048
_refine_ls_R_factor_gt           0.030
_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)+(0.0508P)²+0.0084P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.073
_refine_ls_wR_factor_ref         0.080
_reflns_number_gt                960
_reflns_number_total             1185
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg1180.cif
_cod_data_source_block           III
_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      'P 21'
_cod_database_code               2013616
_cod_database_fobs_code          2013616
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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 0.7189(3) 1.2636(7) 0.7834(2) 0.0316(7) Uani d . 1 . . C
C2 0.6973(3) 1.2471(7) 0.8929(2) 0.0370(8) Uani d . 1 . . C
C3 0.7709(3) 1.4128(10) 0.9641(2) 0.0449(8) Uani d . 1 . . C
H3 0.7553 1.3986 1.0367 0.054 Uiso calc R 1 . . H
C4 0.8635(3) 1.5918(8) 0.9288(2) 0.0420(8) Uani d . 1 . . C
H4 0.9114 1.6981 0.9777 0.05 Uiso calc R 1 . . H
C5 0.8896(3) 1.6221(7) 0.8192(2) 0.0347(7) Uani d . 1 . . C
C6 0.9850(3) 1.8124(7) 0.7823(2) 0.0411(9) Uani d . 1 . . C
H6 1.0304 1.9224 0.8311 0.049 Uiso calc R 1 . . H
C7 1.0123(3) 1.8391(7) 0.6774(3) 0.0446(9) Uani d . 1 . . C
H7 1.0769 1.9639 0.6545 0.054 Uiso calc R 1 . . H
C8 0.9418(3) 1.6760(8) 0.6037(3) 0.0437(9) Uani d . 1 . . C
H8 0.9595 1.6946 0.5316 0.052 Uiso calc R 1 . . H
C9 0.8475(3) 1.4902(7) 0.6359(2) 0.0393(9) Uani d . 1 . . C
H9 0.802 1.3847 0.5854 0.047 Uiso calc R 1 . . H
C10 0.8180(3) 1.4559(6) 0.7452(2) 0.0297(7) Uani d . 1 . . C
C11 0.6458(3) 1.0903(7) 0.7094(2) 0.0344(8) Uani d . 1 . . C
H11 0.6622 1.1093 0.6371 0.041 Uiso calc R 1 . . H
C12 0.4029(3) 0.5752(7) 0.6778(2) 0.0322(7) Uani d . 1 . . C
C13 0.2726(4) 0.3358(7) 0.8131(3) 0.0491(10) Uani d . 1 . . C
H13A 0.1792 0.3689 0.7818 0.074 Uiso calc R 1 . . H
H13B 0.2666 0.3386 0.8892 0.074 Uiso calc R 1 . . H
H13C 0.3059 0.169 0.7905 0.074 Uiso calc R 1 . . H
N1 0.5593(2) 0.9109(7) 0.73939(17) 0.0350(6) Uani d . 1 . . N
N2 0.4992(3) 0.7659(6) 0.65886(19) 0.0378(7) Uani d . 1 . . N
N3 0.3719(3) 0.5329(6) 0.7795(2) 0.0393(7) Uani d . 1 . . N
O1 0.6057(3) 1.0745(6) 0.93639(18) 0.0474(6) Uani d . 1 . . O
S1 0.32963(8) 0.4069(2) 0.57655(6) 0.0454(3) Uani d . 1 . . S
H1A 0.566(5) 0.993(13) 0.874(4) 0.12(2) Uiso d . 1 . . H
H2A 0.518(3) 0.806(7) 0.589(2) 0.041(9) Uiso d . 1 . . H
H3A 0.417(4) 0.622(9) 0.827(3) 0.064(13) 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
4 1 -5
5 1 -2
0 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 118.4(3) ?
C2 C1 C11 121.2(3) ?
C10 C1 C11 120.3(2) ?
O1 C2 C1 122.8(3) ?
O1 C2 C3 116.4(3) ?
C1 C2 C3 120.7(3) ?
C4 C3 C2 120.9(3) ?
C4 C3 H3 119.5 ?
C2 C3 H3 119.5 ?
C3 C4 C5 121.6(3) ?
C3 C4 H4 119.2 ?
C5 C4 H4 119.2 ?
C6 C5 C4 121.5(3) ?
C6 C5 C10 119.6(3) ?
C4 C5 C10 118.9(3) ?
C7 C6 C5 121.7(3) ?
C7 C6 H6 119.2 ?
C5 C6 H6 119.2 ?
C6 C7 C8 119.0(3) ?
C6 C7 H7 120.5 ?
C8 C7 H7 120.5 ?
C9 C8 C7 121.3(3) ?
C9 C8 H8 119.4 ?
C7 C8 H8 119.4 ?
C8 C9 C10 120.9(3) ?
C8 C9 H9 119.5 ?
C10 C9 H9 119.5 ?
C9 C10 C5 117.5(3) ?
C9 C10 C1 123.1(3) ?
C5 C10 C1 119.4(2) ?
N1 C11 C1 122.9(3) yes
N1 C11 H11 118.5 ?
C1 C11 H11 118.5 ?
N3 C12 N2 116.4(3) yes
N3 C12 S1 123.4(3) ?
N2 C12 S1 120.2(2) ?
N3 C13 H13A 109.5 ?
N3 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
N3 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
C11 N1 N2 115.1(2) yes
C12 N2 N1 121.8(2) yes
C12 N2 H2A 118(2) ?
N1 N2 H2A 120(2) ?
C12 N3 C13 123.3(3) yes
C12 N3 H3A 118(3) ?
C13 N3 H3A 119(3) ?
C2 O1 H1A 101(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
C1 C2 . 1.397(4) ?
C1 C10 . 1.444(4) ?
C1 C11 . 1.447(4) ?
C2 O1 . 1.356(4) yes
C2 C3 . 1.404(5) ?
C3 C4 . 1.345(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.412(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.409(4) ?
C5 C10 . 1.420(4) ?
C6 C7 . 1.355(5) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.402(5) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.367(5) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.417(4) ?
C9 H9 . 0.9300 ?
C11 N1 . 1.288(4) yes
C11 H11 . 0.9300 ?
C12 N3 . 1.333(4) yes
C12 N2 . 1.355(4) yes
C12 S1 . 1.672(3) yes
C13 N3 . 1.443(4) yes
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
N1 N2 . 1.367(4) yes
N2 H2A . 0.92(3) ?
N3 H3A . 0.85(4) ?
O1 H1A . 0.95(5) ?
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 . 0.95(5) 1.75(5) 2.641(3) 155(5)
N3 H3A N1 . 0.85(4) 2.29(4) 2.671(4) 107(3)
N2 H2A S1 2_656 0.92(3) 2.60(3) 3.467(3) 158(2)
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 179.5(3)
C11 C1 C2 O1 -1.5(5)
C10 C1 C2 C3 -0.3(5)
C11 C1 C2 C3 178.7(3)
O1 C2 C3 C4 -179.6(3)
C1 C2 C3 C4 0.2(5)
C2 C3 C4 C5 0.5(6)
C3 C4 C5 C6 179.0(3)
C3 C4 C5 C10 -1.1(5)
C4 C5 C6 C7 178.8(3)
C10 C5 C6 C7 -1.0(5)
C5 C6 C7 C8 1.1(5)
C6 C7 C8 C9 -0.6(5)
C7 C8 C9 C10 -0.1(5)
C8 C9 C10 C5 0.2(4)
C8 C9 C10 C1 179.7(3)
C6 C5 C10 C9 0.3(4)
C4 C5 C10 C9 -179.5(3)
C6 C5 C10 C1 -179.2(3)
C4 C5 C10 C1 1.0(4)
C2 C1 C10 C9 -179.7(3)
C11 C1 C10 C9 1.2(4)
C2 C1 C10 C5 -0.3(4)
C11 C1 C10 C5 -179.3(3)
C2 C1 C11 N1 -0.9(5)
C10 C1 C11 N1 178.1(3)
C1 C11 N1 N2 179.7(3)
N3 C12 N2 N1 -1.3(4)
S1 C12 N2 N1 178.7(2)
C11 N1 N2 C12 -178.1(3)
N2 C12 N3 C13 -179.5(3)
S1 C12 N3 C13 0.5(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12250939
