#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/48/2014824.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_2014824
loop_
_publ_author_name
'Ján Imrich'
'Mária Vilková'
'Juraj Černák'
_publ_section_title
;
 2-(Acridin-9-ylimino)-3-dimethylamino-1,3-thiazolidin-4-one
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o231
_journal_page_last               o233
_journal_paper_doi               10.1107/S0108270105005044
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C18 H16 N4 O1 S1'
_chemical_formula_moiety         'C18 H16 N4 O1 S1'
_chemical_formula_sum            'C18 H16 N4 O S'
_chemical_formula_weight         336.42
_chemical_name_common
2-(Acridin-9-ylimino)-3-(dimethylamino)-1,3-thiazolidin-4-one
_chemical_name_systematic
;
2-(Acridin-9-ylimino)-3-dimethylamino-1,3-thiazolidin-4-one
;
_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                 105.326(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.282(5)
_cell_length_b                   19.456(5)
_cell_length_c                   11.954(5)
_cell_measurement_reflns_used    3118
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.05
_cell_volume                     1633.4(14)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'DIAMOND (Crystal Impact, 2000)'
_computing_publication_material  'program (reference)?'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean '8.192 pixels/mm'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0565
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8245
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.05
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker 1999)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.256
_refine_ls_extinction_coef       0.0023(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.871
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         2867
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.871
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0353
_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)+(0.0351P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0785
_reflns_number_gt                1776
_reflns_number_total             2867
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd1369.cif
_cod_data_source_block           IV
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C18 H16 N4 O1 S1'
_cod_database_code               2014824
_cod_database_fobs_code          2014824
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_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 0.30409(8) 0.33825(3) 0.10522(5) 0.04651(19) Uani d . 1 . . S
O1 0.0638(2) 0.46877(7) -0.13032(13) 0.0483(4) Uani d . 1 . . O
N1 0.9133(2) 0.19210(9) 0.24539(16) 0.0469(5) Uani d . 1 . . N
N2 0.5803(2) 0.32560(9) -0.00933(15) 0.0429(5) Uani d . 1 . . N
N3 0.3238(2) 0.39793(8) -0.08672(13) 0.0366(4) Uani d . 1 . . N
N4 0.3830(2) 0.41895(9) -0.18407(15) 0.0455(5) Uani d . 1 . . N
C1 0.8163(3) 0.37932(12) 0.2086(2) 0.0454(6) Uani d . 1 . . C
H1 0.746(3) 0.4113(10) 0.1552(19) 0.053(7) Uiso d . 1 . . H
C2 0.9333(3) 0.40223(14) 0.3084(2) 0.0534(6) Uani d . 1 . . C
H2 0.937(3) 0.4497(11) 0.3278(18) 0.054(7) Uiso d . 1 . . H
C3 1.0400(4) 0.35528(15) 0.3900(2) 0.0590(7) Uani d . 1 . . C
H3 1.118(3) 0.3742(10) 0.4576(18) 0.051(7) Uiso d . 1 . . H
C4 1.0306(3) 0.28751(14) 0.3688(2) 0.0545(7) Uani d . 1 . . C
H4 1.101(3) 0.2557(11) 0.4238(18) 0.053(6) Uiso d . 1 . . H
C5 0.8044(3) 0.09588(12) 0.1220(2) 0.0524(6) Uani d . 1 . . C
H5 0.880(3) 0.0693(10) 0.1806(17) 0.043(6) Uiso d . 1 . . H
C6 0.6941(4) 0.06853(14) 0.0237(2) 0.0577(7) Uani d . 1 . . C
H6 0.698(3) 0.0202(12) 0.013(2) 0.071(8) Uiso d . 1 . . H
C7 0.5741(4) 0.11024(14) -0.0614(2) 0.0579(7) Uani d . 1 . . C
H7 0.500(3) 0.0891(11) -0.132(2) 0.071(8) Uiso d . 1 . . H
C8 0.5700(3) 0.17908(14) -0.0456(2) 0.0503(6) Uani d . 1 . . C
H8 0.490(3) 0.2086(10) -0.1031(19) 0.055(7) Uiso d . 1 . . H
C10 0.6839(3) 0.21028(11) 0.05681(18) 0.0401(5) Uani d . 1 . . C
C11 0.8028(3) 0.16762(11) 0.14404(19) 0.0425(5) Uani d . 1 . . C
C12 0.9123(3) 0.26043(11) 0.26361(19) 0.0430(5) Uani d . 1 . . C
C13 0.8002(3) 0.30799(11) 0.18189(18) 0.0382(5) Uani d . 1 . . C
C9 0.6831(3) 0.28118(11) 0.07814(17) 0.0390(5) Uani d . 1 . . C
C14 0.4236(3) 0.35167(10) -0.00316(17) 0.0360(5) Uani d . 1 . . C
C15 0.1063(3) 0.39156(14) 0.0298(2) 0.0475(6) Uani d . 1 . . C
H15A 0.084(3) 0.4243(10) 0.0830(17) 0.049(6) Uiso d . 1 . . H
H15B -0.002(3) 0.3631(12) 0.006(2) 0.074(8) Uiso d . 1 . . H
C16 0.1567(3) 0.42451(11) -0.07050(18) 0.0375(5) Uani d . 1 . . C
C17 0.5622(4) 0.45742(17) -0.1534(3) 0.0620(7) Uani d . 1 . . C
H17A 0.672(4) 0.4260(14) -0.124(2) 0.104(11) Uiso d . 1 . . H
H17B 0.577(3) 0.4775(13) -0.221(2) 0.088(9) Uiso d . 1 . . H
H17C 0.555(4) 0.4913(14) -0.096(3) 0.101(11) Uiso d . 1 . . H
C18 0.3777(4) 0.36265(17) -0.2658(2) 0.0614(8) Uani d . 1 . . C
H18A 0.254(4) 0.3391(14) -0.279(2) 0.101(10) Uiso d . 1 . . H
H18B 0.396(4) 0.3843(13) -0.332(2) 0.089(9) Uiso d . 1 . . H
H18C 0.485(3) 0.3316(12) -0.236(2) 0.074(8) 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'
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
_geom_angle_publ_flag
C14 S1 C15 91.81(11) y
C12 N1 C11 117.71(18) y
C14 N2 C9 120.77(17) y
C16 N3 C14 116.84(17) y
C16 N3 N4 118.78(16) y
C14 N3 N4 124.38(16) y
N3 N4 C18 112.08(18) y
N3 N4 C17 112.91(19) y
C18 N4 C17 114.5(2) y
C2 C1 C13 121.2(2) ?
C2 C1 H1 119.1(13) ?
C13 C1 H1 119.7(13) ?
C1 C2 C3 120.2(3) ?
C1 C2 H2 120.5(13) ?
C3 C2 H2 119.1(13) ?
C4 C3 C2 121.0(3) ?
C4 C3 H3 122.7(13) ?
C2 C3 H3 116.3(13) ?
C3 C4 C12 121.3(2) ?
C3 C4 H4 121.2(13) ?
C12 C4 H4 117.4(13) ?
C6 C5 C11 121.2(2) ?
C6 C5 H5 122.7(12) ?
C11 C5 H5 116.1(12) ?
C5 C6 C7 121.0(3) ?
C5 C6 H6 118.8(15) ?
C7 C6 H6 120.2(15) ?
C8 C7 C6 120.1(3) ?
C8 C7 H7 121.0(14) ?
C6 C7 H7 118.9(14) ?
C7 C8 C10 120.9(2) ?
C7 C8 H8 121.4(12) ?
C10 C8 H8 117.7(12) ?
C9 C10 C8 123.2(2) ?
C9 C10 C11 117.9(2) ?
C8 C10 C11 118.9(2) ?
N1 C11 C5 118.7(2) ?
N1 C11 C10 123.4(2) ?
C5 C11 C10 117.9(2) ?
N1 C12 C4 118.7(2) ?
N1 C12 C13 123.6(2) ?
C4 C12 C13 117.7(2) ?
C9 C13 C1 123.70(19) ?
C9 C13 C12 117.69(19) ?
C1 C13 C12 118.6(2) ?
C10 C9 C13 119.62(19) ?
C10 C9 N2 119.67(19) ?
C13 C9 N2 120.40(19) ?
N2 C14 N3 121.46(18) ?
N2 C14 S1 127.64(16) ?
N3 C14 S1 110.90(14) ?
C16 C15 S1 108.36(16) ?
C16 C15 H15A 112.0(12) ?
S1 C15 H15A 107.8(12) ?
C16 C15 H15B 111.7(15) ?
S1 C15 H15B 107.8(14) ?
H15A C15 H15B 109.0(19) ?
O1 C16 N3 124.10(19) ?
O1 C16 C15 124.47(19) ?
N3 C16 C15 111.43(18) ?
N4 C17 H17A 110.8(15) ?
N4 C17 H17B 107.5(16) ?
H17A C17 H17B 107(2) ?
N4 C17 H17C 108.3(16) ?
H17A C17 H17C 111(2) ?
H17B C17 H17C 112(2) ?
N4 C18 H18A 108.2(16) ?
N4 C18 H18B 104.1(16) ?
H18A C18 H18B 114(2) ?
N4 C18 H18C 110.1(14) ?
H18A C18 H18C 112(2) ?
H18B C18 H18C 108(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
S1 C14 . 1.761(2) y
S1 C15 . 1.810(2) y
O1 C16 . 1.206(2) y
N1 C12 . 1.347(2) y
N1 C11 . 1.352(3) y
N2 C14 . 1.269(2) y
N2 C9 . 1.409(2) y
N3 C16 . 1.383(2) y
N3 C14 . 1.397(2) y
N3 N4 . 1.404(2) y
N4 C18 . 1.461(3) y
N4 C17 . 1.465(3) y
C1 C2 . 1.346(3) ?
C1 C13 . 1.422(3) ?
C1 H1 . 0.94(2) ?
C2 C3 . 1.410(3) ?
C2 H2 . 0.95(2) ?
C3 C4 . 1.341(3) ?
C3 H3 . 0.93(2) ?
C4 C12 . 1.424(3) ?
C4 H4 . 0.95(2) ?
C5 C6 . 1.345(3) ?
C5 C11 . 1.421(3) ?
C5 H5 . 0.927(19) ?
C6 C7 . 1.410(3) ?
C6 H6 . 0.95(2) ?
C7 C8 . 1.354(3) ?
C7 H7 . 0.97(2) ?
C8 C10 . 1.421(3) ?
C8 H8 . 0.96(2) ?
C10 C9 . 1.403(3) ?
C10 C11 . 1.431(3) ?
C12 C13 . 1.434(3) ?
C13 C9 . 1.407(3) ?
C15 C16 . 1.488(3) ?
C15 H15A . 0.94(2) ?
C15 H15B . 0.94(2) ?
C17 H17A . 0.99(3) ?
C17 H17B . 0.93(3) ?
C17 H17C . 0.96(3) ?
C18 H18A . 0.99(3) ?
C18 H18B . 0.94(3) ?
C18 H18C . 0.98(2) ?
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
C5 H5 O1 4_666 0.93(2) 2.42(2) 3.311(4) 161.7(17) y
C15 H15A O1 3_565 0.94(2) 2.48(2) 3.339(4) 152.1(16) y
C18 H18B Cg 4_565 0.94(3) 2.97(3) 3.645(4) 131(2) y
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
C16 N3 N4 C18 -113.6(2)
C14 N3 N4 C18 66.9(3)
C16 N3 N4 C17 115.3(2)
C14 N3 N4 C17 -64.2(3)
C13 C1 C2 C3 -1.3(3)
C1 C2 C3 C4 1.6(4)
C2 C3 C4 C12 -0.2(4)
C11 C5 C6 C7 0.5(4)
C5 C6 C7 C8 0.7(4)
C6 C7 C8 C10 -0.7(4)
C7 C8 C10 C9 -179.2(2)
C7 C8 C10 C11 -0.5(3)
C12 N1 C11 C5 178.82(18)
C12 N1 C11 C10 -0.9(3)
C6 C5 C11 N1 178.6(2)
C6 C5 C11 C10 -1.7(3)
C9 C10 C11 N1 0.1(3)
C8 C10 C11 N1 -178.61(19)
C9 C10 C11 C5 -179.59(18)
C8 C10 C11 C5 1.7(3)
C11 N1 C12 C4 -178.78(19)
C11 N1 C12 C13 0.3(3)
C3 C4 C12 N1 177.8(2)
C3 C4 C12 C13 -1.3(3)
C2 C1 C13 C9 -178.8(2)
C2 C1 C13 C12 -0.2(3)
N1 C12 C13 C9 1.1(3)
C4 C12 C13 C9 -179.86(19)
N1 C12 C13 C1 -177.58(19)
C4 C12 C13 C1 1.5(3)
C8 C10 C9 C13 179.95(18)
C11 C10 C9 C13 1.3(3)
C8 C10 C9 N2 -6.5(3)
C11 C10 C9 N2 174.81(16)
C1 C13 C9 C10 176.76(19)
C12 C13 C9 C10 -1.8(3)
C1 C13 C9 N2 3.3(3)
C12 C13 C9 N2 -175.31(17)
C14 N2 C9 C10 105.3(2)
C14 N2 C9 C13 -81.2(2)
C9 N2 C14 N3 177.41(18)
C9 N2 C14 S1 -1.5(3)
C16 N3 C14 N2 -178.60(18)
N4 N3 C14 N2 1.0(3)
C16 N3 C14 S1 0.5(2)
N4 N3 C14 S1 -179.95(14)
C15 S1 C14 N2 -177.0(2)
C15 S1 C14 N3 4.03(16)
C14 S1 C15 C16 -7.05(18)
C14 N3 C16 O1 174.02(19)
N4 N3 C16 O1 -5.6(3)
C14 N3 C16 C15 -6.0(2)
N4 N3 C16 C15 174.34(18)
S1 C15 C16 O1 -171.51(17)
S1 C15 C16 N3 8.5(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21181141
