#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/75/2017501.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_2017501
loop_
_publ_author_name
'Potočňák, Ivan'
'Imrich, Ján'
'Danihel, Ivan'
'Kožíšek, Jozef'
'Klika, Karel Douglas'
_publ_section_title
;
 4-(9,10-Dihydroacridin-9-ylidene)thiosemicarbazide and its
 five-membered thiazole and six-membered thiazine derivatives
;
_journal_coeditor_code           DN3135
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o87
_journal_page_last               o92
_journal_paper_doi               10.1107/S0108270110001277
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H12 N4 S'
_chemical_formula_moiety         'C14 H12 N4 S'
_chemical_formula_sum            'C14 H12 N4 S'
_chemical_formula_weight         268.34
_chemical_melting_point          483
_chemical_name_systematic
;
4-(9,10-dihydroacridin-9-ylidene)thiosemicarbazide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 99.372(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6535(5)
_cell_length_b                   18.6374(9)
_cell_length_c                   7.8350(6)
_cell_measurement_reflns_used    2725
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5790
_cell_measurement_theta_min      2.6243
_cell_volume                     1246.75(14)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2000)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008); PARST ? (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur2 with Sapphire2 CCD detector
;
_diffrn_measurement_method
'Rotation method data acquisition using ω scans'
_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  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0667
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13277
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.85
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(Clark & Reid, 1995)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.3550
_exptl_crystal_size_mid          0.1162
_exptl_crystal_size_min          0.0784
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.1078
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0265P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0696
_refine_ls_wR_factor_ref         0.0766
_reflns_number_gt                1077
_reflns_number_total             2208
_reflns_threshold_expression     I>2s(I)
_cod_data_source_file            dn3135.cif
_cod_data_source_block           III
_cod_original_cell_volume        1246.75(13)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               2017501
_cod_database_fobs_code          2017501
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
N N3 0.4003(3) 0.40293(13) 0.5112(3) 0.0749(7) Uani d . 1 . .
H H4 0.471(3) 0.4309(14) 0.483(3) 0.118(12) Uiso d . 1 . .
H H5 0.395(3) 0.3524(15) 0.490(3) 0.118(11) Uiso d . 1 . .
C C2 0.2959(3) 0.43085(11) 0.5905(3) 0.0529(6) Uani d . 1 . .
S S1A 0.3067(7) 0.51590(11) 0.6540(11) 0.0769(15) Uani d P 0.730(15) . .
S S1B 0.2404(15) 0.5239(3) 0.558(2) 0.063(2) Uani d P 0.270(15) . .
N N12' 0.1889(3) 0.38506(11) 0.6358(3) 0.0666(7) Uani d . 1 . .
H H12' 0.146(4) 0.4010(18) 0.712(4) 0.168(17) Uiso d . 1 . .
N N11' 0.2136(2) 0.31255(10) 0.6142(2) 0.0525(5) Uani d . 1 . .
C C9' 0.1116(3) 0.26535(11) 0.6485(3) 0.0415(6) Uani d . 1 . .
C C8A' -0.0407(3) 0.27492(11) 0.7008(3) 0.0412(6) Uani d . 1 . .
C C8' -0.1157(3) 0.34000(12) 0.7105(3) 0.0715(8) Uani d . 1 . .
H H8' -0.0657 0.3817 0.6839 0.086 Uiso calc R 1 . .
C C7' -0.2607(3) 0.34525(14) 0.7580(4) 0.0829(8) Uani d . 1 . .
H H7' -0.3063 0.3901 0.7643 0.100 Uiso calc R 1 . .
C C6' -0.3392(3) 0.28501(14) 0.7962(3) 0.0690(7) Uani d . 1 . .
H H6' -0.4373 0.2888 0.8294 0.083 Uiso calc R 1 . .
C C5' -0.2726(3) 0.22031(13) 0.7852(3) 0.0628(7) Uani d . 1 . .
H H5' -0.3257 0.1792 0.8098 0.075 Uiso calc R 1 . .
C C10A' -0.1258(3) 0.21421(12) 0.7375(3) 0.0482(6) Uani d . 1 . .
N N10' -0.0644(3) 0.14714(11) 0.7248(3) 0.0675(7) Uani d . 1 . .
H H10' -0.114(3) 0.1130(12) 0.753(3) 0.069(9) Uiso d . 1 . .
C C4A' 0.0733(3) 0.13409(12) 0.6661(3) 0.0508(6) Uani d . 1 . .
C C4' 0.1214(3) 0.06328(12) 0.6461(3) 0.0656(7) Uani d . 1 . .
H H4' 0.0599 0.0253 0.6729 0.079 Uiso calc R 1 . .
C C3' 0.2576(4) 0.05016(14) 0.5876(3) 0.0773(8) Uani d . 1 . .
H H3' 0.2887 0.0031 0.5726 0.093 Uiso calc R 1 . .
C C2' 0.3500(3) 0.10631(14) 0.5502(3) 0.0782(8) Uani d . 1 . .
H H2' 0.4441 0.0971 0.5114 0.094 Uiso calc R 1 . .
C C1' 0.3037(3) 0.17562(12) 0.5701(3) 0.0598(7) Uani d . 1 . .
H H1' 0.3675 0.2130 0.5447 0.072 Uiso calc R 1 . .
C C9A' 0.1635(3) 0.19160(10) 0.6273(3) 0.0426(6) Uani d . 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
C2 N3 H4 . . 117.5(18) ?
C2 N3 H5 . . 117.9(16) ?
H4 N3 H5 . . 125(2) ?
N3 C2 N12' . . 115.9(2) ?
N3 C2 S1A . . 121.4(2) ?
N12' C2 S1A . . 122.2(2) ?
N3 C2 S1B . . 120.8(3) ?
N12' C2 S1B . . 117.8(3) ?
S1A C2 S1B . . 29.1(2) ?
S1B S1A C2 . . 84.8(5) ?
S1A S1B C2 . . 66.1(7) ?
C2 N12' N11' . . 117.4(2) yes
C2 N12' H12' . . 112(2) ?
N11' N12' H12' . . 123(2) ?
C9' N11' N12' . . 120.75(18) yes
N11' C9' C8A' . . 130.54(19) ?
N11' C9' C9A' . . 112.3(2) ?
C8A' C9' C9A' . . 117.12(19) ?
C8' C8A' C10A' . . 115.4(2) ?
C8' C8A' C9' . . 125.3(2) ?
C10A' C8A' C9' . . 119.22(19) ?
C7' C8' C8A' . . 122.4(2) ?
C7' C8' H8' . . 118.8 ?
C8A' C8' H8' . . 118.8 ?
C8' C7' C6' . . 120.7(2) ?
C8' C7' H7' . . 119.7 ?
C6' C7' H7' . . 119.7 ?
C5' C6' C7' . . 119.2(2) ?
C5' C6' H6' . . 120.4 ?
C7' C6' H6' . . 120.4 ?
C6' C5' C10A' . . 120.8(2) ?
C6' C5' H5' . . 119.6 ?
C10A' C5' H5' . . 119.6 ?
N10' C10A' C5' . . 118.6(2) ?
N10' C10A' C8A' . . 119.9(2) ?
C5' C10A' C8A' . . 121.5(2) ?
C4A' N10' C10A' . . 123.8(2) ?
C4A' N10' H10' . . 118.6(16) ?
C10A' N10' H10' . . 117.6(16) ?
N10' C4A' C9A' . . 119.2(2) ?
N10' C4A' C4' . . 119.8(2) ?
C9A' C4A' C4' . . 121.0(2) ?
C3' C4' C4A' . . 119.9(2) ?
C3' C4' H4' . . 120.0 ?
C4A' C4' H4' . . 120.0 ?
C4' C3' C2' . . 120.2(2) ?
C4' C3' H3' . . 119.9 ?
C2' C3' H3' . . 119.9 ?
C1' C2' C3' . . 120.1(2) ?
C1' C2' H2' . . 119.9 ?
C3' C2' H2' . . 119.9 ?
C2' C1' C9A' . . 121.7(2) ?
C2' C1' H1' . . 119.2 ?
C9A' C1' H1' . . 119.2 ?
C4A' C9A' C1' . . 117.1(2) ?
C4A' C9A' C9' . . 120.4(2) ?
C1' C9A' C9' . . 122.4(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
N3 C2 . 1.286(3) yes
N3 H4 . 0.86(3) ?
N3 H5 . 0.96(3) ?
C2 N12' . 1.349(3) yes
C2 S1A . 1.659(3) ?
C2 S1B . 1.807(9) ?
S1A S1B . 0.883(9) ?
N12' N11' . 1.383(2) yes
N12' H12' . 0.81(3) ?
N11' C9' . 1.304(2) yes
C9' C8A' . 1.454(3) yes
C9' C9A' . 1.464(3) yes
C8A' C8' . 1.384(3) ?
C8A' C10A' . 1.405(3) ?
C8' C7' . 1.369(3) ?
C8' H8' . 0.9300 ?
C7' C6' . 1.371(3) ?
C7' H7' . 0.9300 ?
C6' C5' . 1.345(3) ?
C6' H6' . 0.9300 ?
C5' C10A' . 1.386(3) ?
C5' H5' . 0.9300 ?
C10A' N10' . 1.368(3) ?
N10' C4A' . 1.367(3) ?
N10' H10' . 0.82(2) ?
C4A' C9A' . 1.388(3) ?
C4A' C4' . 1.400(3) ?
C4' C3' . 1.354(3) ?
C4' H4' . 0.9300 ?
C3' C2' . 1.377(3) ?
C3' H3' . 0.9300 ?
C2' C1' . 1.369(3) ?
C2' H2' . 0.9300 ?
C1' C9A' . 1.393(3) ?
C1' H1' . 0.9300 ?
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
N3 H5 N11' . 0.96(3) 2.11(3) 2.554(3) 106.3(19)
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
N3 C2 S1A S1B . . . . 97.7(5) ?
N12' C2 S1A S1B . . . . -90.1(5) ?
N3 C2 S1B S1A . . . . -100.3(5) ?
N12' C2 S1B S1A . . . . 107.0(5) ?
N3 C2 N12' N11' . . . . 8.4(3) yes
S1A C2 N12' N11' . . . . -164.1(4) ?
S1B C2 N12' N11' . . . . 162.5(6) ?
C2 N12' N11' C9' . . . . -177.1(2) ?
N12' N11' C9' C8A' . . . . 4.1(3) ?
N12' N11' C9' C9A' . . . . -176.6(2) yes
N11' C9' C8A' C8' . . . . 6.0(4) ?
C9A' C9' C8A' C8' . . . . -173.2(2) ?
N11' C9' C8A' C10A' . . . . -177.2(2) ?
C9A' C9' C8A' C10A' . . . . 3.5(3) ?
C10A' C8A' C8' C7' . . . . 2.0(3) ?
C9' C8A' C8' C7' . . . . 178.8(2) ?
C8A' C8' C7' C6' . . . . -0.8(4) ?
C8' C7' C6' C5' . . . . -0.6(4) ?
C7' C6' C5' C10A' . . . . 0.6(4) ?
C6' C5' C10A' N10' . . . . -178.7(2) ?
C6' C5' C10A' C8A' . . . . 0.7(3) ?
C8' C8A' C10A' N10' . . . . 177.5(2) ?
C9' C8A' C10A' N10' . . . . 0.4(3) ?
C8' C8A' C10A' C5' . . . . -1.9(3) ?
C9' C8A' C10A' C5' . . . . -178.96(19) ?
C5' C10A' N10' C4A' . . . . 174.7(2) ?
C8A' C10A' N10' C4A' . . . . -4.7(3) ?
C10A' N10' C4A' C9A' . . . . 4.5(3) ?
C10A' N10' C4A' C4' . . . . -175.5(2) ?
N10' C4A' C4' C3' . . . . 179.8(2) ?
C9A' C4A' C4' C3' . . . . -0.1(4) ?
C4A' C4' C3' C2' . . . . 1.0(4) ?
C4' C3' C2' C1' . . . . -0.8(4) ?
C3' C2' C1' C9A' . . . . -0.2(4) ?
N10' C4A' C9A' C1' . . . . 179.2(2) ?
C4' C4A' C9A' C1' . . . . -0.8(3) ?
N10' C4A' C9A' C9' . . . . -0.1(3) ?
C4' C4A' C9A' C9' . . . . 179.9(2) ?
C2' C1' C9A' C4A' . . . . 1.0(3) ?
C2' C1' C9A' C9' . . . . -179.7(2) ?
N11' C9' C9A' C4A' . . . . 176.92(19) ?
C8A' C9' C9A' C4A' . . . . -3.7(3) ?
N11' C9' C9A' C1' . . . . -2.4(3) ?
C8A' C9' C9A' C1' . . . . 176.99(19) ?
