#------------------------------------------------------------------------------
#$Date: 2016-10-29 04:43:26 +0300 (Sat, 29 Oct 2016) $
#$Revision: 187672 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/44/1544402.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_1544402
loop_
_publ_author_name
'Hong, Li'
'Xin, Zhang'
_publ_section_title
;
 (E)-4-(Benzo[d]thiazol-2-yl)-N-(pyridin-3-ylmethylidene)aniline
 hemihydrate
;
_journal_issue                   10
_journal_name_full               IUCrData
_journal_page_first              x161608
_journal_paper_doi               10.1107/S2414314616016084
_journal_volume                  1
_journal_year                    2016
_chemical_formula_iupac          'C19 H13 N3 S, 0.5H2 O'
_chemical_formula_moiety         'C19 H13 N3 S, 0.5(H2 O)'
_chemical_formula_sum            'C19 H14 N3 O0.5 S'
_chemical_formula_weight         324.39
_chemical_name_systematic
'(E)-4-(Benzo[d]thiazol-2-yl)-N-(pyridin-3-ylmethylidene)aniline hemihydrate'
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 97.601(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            8
_cell_length_a                   34.026(5)
_cell_length_b                   10.447(5)
_cell_length_c                   8.967(5)
_cell_measurement_reflns_used    5584
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.67
_cell_measurement_theta_min      2.42
_cell_volume                     3159(2)
_computing_cell_refinement
;
SAINT (Bruker, 2002)
;
_computing_data_collection
;
SMART (Bruker, 2002)
;
_computing_data_reduction
;
SAINT (Bruker, 2002)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL-97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0166
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11032
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.21
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.9570
_exptl_absorpt_correction_T_min  0.9530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2002)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.231
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2794
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0338
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1309
_reflns_number_gt                2444
_reflns_number_total             2794
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            su4071sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c  '
_cod_database_code               1544402
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_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_symmetry_multiplicity
S S1 0.640666(11) 0.04206(4) 0.17319(4) 0.0537(2) Uani d . 1 1
N N1 0.66886(3) 0.21158(11) 0.37023(13) 0.0455(3) Uani d . 1 1
O O1 1.0000 0.35524(18) 0.2500 0.0718(5) Uani d S 1 2
C C6 0.63000(4) 0.18945(13) 0.39216(15) 0.0449(3) Uani d . 1 1
N N2 0.83432(4) 0.14991(12) 0.10104(14) 0.0518(3) Uani d . 1 1
C C1 0.60952(4) 0.09943(13) 0.29545(16) 0.0477(4) Uani d . 1 1
C C7 0.67836(4) 0.14078(12) 0.26047(15) 0.0424(3) Uani d . 1 1
C C11 0.79462(4) 0.14324(13) 0.13047(16) 0.0459(4) Uani d . 1 1
C C16 0.89930(5) 0.06086(14) -0.16991(18) 0.0546(4) Uani d . 1 1
H H16 0.8817 0.0151 -0.2382 0.066 Uiso calc R 1 1
C C15 0.88592(4) 0.12279(13) -0.05054(15) 0.0455(4) Uani d . 1 1
C C14 0.84443(4) 0.11634(14) -0.02344(16) 0.0475(4) Uani d . 1 1
H H14 0.8253 0.0870 -0.0993 0.057 Uiso calc R 1 1
C C8 0.71788(4) 0.14141(12) 0.21252(15) 0.0420(3) Uani d . 1 1
C C5 0.61062(5) 0.24786(15) 0.50285(18) 0.0539(4) Uani d . 1 1
H H5 0.6237 0.3079 0.5680 0.065 Uiso calc R 1 1
C C12 0.76579(5) 0.06122(15) 0.0601(2) 0.0570(4) Uani d . 1 1
H H12 0.7720 0.0063 -0.0150 0.068 Uiso calc R 1 1
C C13 0.72815(5) 0.06029(15) 0.10019(18) 0.0546(4) Uani d . 1 1
H H13 0.7092 0.0048 0.0517 0.066 Uiso calc R 1 1
C C10 0.78445(5) 0.22285(16) 0.24345(18) 0.0564(4) Uani d . 1 1
H H10 0.8035 0.2773 0.2932 0.068 Uiso calc R 1 1
N N3 0.95197(4) 0.19941(15) 0.02959(16) 0.0677(4) Uani d . 1 1
C C4 0.57205(5) 0.21506(17) 0.51363(19) 0.0616(4) Uani d . 1 1
H H4 0.5589 0.2539 0.5862 0.074 Uiso calc R 1 1
C C2 0.57032(5) 0.06641(16) 0.3070(2) 0.0598(4) Uani d . 1 1
H H2 0.5568 0.0070 0.2420 0.072 Uiso calc R 1 1
C C9 0.74685(4) 0.22258(15) 0.28291(18) 0.0542(4) Uani d . 1 1
H H9 0.7407 0.2776 0.3580 0.065 Uiso calc R 1 1
C C19 0.91367(5) 0.19251(15) 0.04519(18) 0.0562(4) Uani d . 1 1
H H19 0.9049 0.2368 0.1245 0.067 Uiso calc R 1 1
C C17 0.93888(5) 0.06715(17) -0.1874(2) 0.0655(5) Uani d . 1 1
H H17 0.9484 0.0255 -0.2670 0.079 Uiso calc R 1 1
C C3 0.55236(5) 0.12481(17) 0.4178(2) 0.0653(5) Uani d . 1 1
H H3 0.5264 0.1032 0.4288 0.078 Uiso calc R 1 1
C C18 0.96381(5) 0.13569(17) -0.0857(2) 0.0670(5) Uani d . 1 1
H H18 0.9906 0.1382 -0.0972 0.080 Uiso calc R 1 1
H H1 0.9871(7) 0.300(2) 0.188(3) 0.107(8) Uiso d . 1 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'
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
C1 S1 C7 89.23(7)
C7 N1 C6 110.47(12)
N1 C6 C1 115.55(12)
N1 C6 C5 125.20(13)
C1 C6 C5 119.25(13)
C14 N2 C11 122.13(12)
C2 C1 C6 121.50(14)
C2 C1 S1 129.30(13)
C6 C1 S1 109.19(11)
N1 C7 C8 123.18(12)
N1 C7 S1 115.56(11)
C8 C7 S1 121.26(10)
C10 C11 C12 118.12(14)
C10 C11 N2 116.32(13)
C12 C11 N2 125.52(13)
C17 C16 C15 119.62(15)
C17 C16 H16 120.2
C15 C16 H16 120.2
C16 C15 C19 117.20(14)
C16 C15 C14 122.10(13)
C19 C15 C14 120.70(13)
N2 C14 C15 121.06(13)
N2 C14 H14 119.5
C15 C14 H14 119.5
C9 C8 C13 117.97(14)
C9 C8 C7 119.58(13)
C13 C8 C7 122.42(12)
C4 C5 C6 119.01(15)
C4 C5 H5 120.5
C6 C5 H5 120.5
C13 C12 C11 120.77(14)
C13 C12 H12 119.6
C11 C12 H12 119.6
C12 C13 C8 120.99(14)
C12 C13 H13 119.5
C8 C13 H13 119.5
C9 C10 C11 121.16(14)
C9 C10 H10 119.4
C11 C10 H10 119.4
C19 N3 C18 117.01(15)
C5 C4 C3 120.96(15)
C5 C4 H4 119.5
C3 C4 H4 119.5
C3 C2 C1 117.67(16)
C3 C2 H2 121.2
C1 C2 H2 121.2
C10 C9 C8 120.97(14)
C10 C9 H9 119.5
C8 C9 H9 119.5
N3 C19 C15 123.79(15)
N3 C19 H19 118.1
C15 C19 H19 118.1
C18 C17 C16 118.65(16)
C18 C17 H17 120.7
C16 C17 H17 120.7
C2 C3 C4 121.61(15)
C2 C3 H3 119.2
C4 C3 H3 119.2
N3 C18 C17 123.70(16)
N3 C18 H18 118.2
C17 C18 H18 118.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.7297(16)
S1 C7 1.7482(14)
N1 C7 1.3056(18)
N1 C6 1.3818(19)
O1 H1 0.87(2)
C6 C1 1.401(2)
C6 C5 1.402(2)
N2 C14 1.261(2)
N2 C11 1.4118(18)
C1 C2 1.394(2)
C7 C8 1.465(2)
C11 C10 1.389(2)
C11 C12 1.389(2)
C16 C17 1.378(2)
C16 C15 1.378(2)
C16 H16 0.9300
C15 C19 1.394(2)
C15 C14 1.465(2)
C14 H14 0.9300
C8 C9 1.387(2)
C8 C13 1.396(2)
C5 C4 1.372(2)
C5 H5 0.9300
C12 C13 1.375(2)
C12 H12 0.9300
C13 H13 0.9300
C10 C9 1.372(2)
C10 H10 0.9300
N3 C19 1.331(2)
N3 C18 1.336(2)
C4 C3 1.387(3)
C4 H4 0.9300
C2 C3 1.377(2)
C2 H2 0.9300
C9 H9 0.9300
C19 H19 0.9300
C17 C18 1.364(2)
C17 H17 0.9300
C3 H3 0.9300
C18 H18 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
O1 H1 N3 . 0.88(2) 2.03(2) 2.894(2) 170(2)
C2 H2 O1 3_445 0.93 2.51 3.245(3) 136
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 N1 C6 C1 -0.22(17)
C7 N1 C6 C5 178.72(13)
N1 C6 C1 C2 178.88(13)
C5 C6 C1 C2 -0.1(2)
N1 C6 C1 S1 -0.18(16)
C5 C6 C1 S1 -179.19(11)
C7 S1 C1 C2 -178.59(16)
C7 S1 C1 C6 0.39(11)
C6 N1 C7 C8 -178.89(11)
C6 N1 C7 S1 0.54(15)
C1 S1 C7 N1 -0.56(11)
C1 S1 C7 C8 178.88(11)
C14 N2 C11 C10 -157.22(14)
C14 N2 C11 C12 25.2(2)
C17 C16 C15 C19 1.7(2)
C17 C16 C15 C14 -178.10(14)
C11 N2 C14 C15 -179.28(12)
C16 C15 C14 N2 164.97(15)
C19 C15 C14 N2 -14.8(2)
N1 C7 C8 C9 -1.6(2)
S1 C7 C8 C9 178.97(11)
N1 C7 C8 C13 176.59(13)
S1 C7 C8 C13 -2.81(19)
N1 C6 C5 C4 -178.82(13)
C1 C6 C5 C4 0.1(2)
C10 C11 C12 C13 0.8(2)
N2 C11 C12 C13 178.31(14)
C11 C12 C13 C8 -0.1(3)
C9 C8 C13 C12 -0.3(2)
C7 C8 C13 C12 -178.52(14)
C12 C11 C10 C9 -1.2(2)
N2 C11 C10 C9 -178.94(13)
C6 C5 C4 C3 0.5(2)
C6 C1 C2 C3 -0.5(2)
S1 C1 C2 C3 178.41(12)
C11 C10 C9 C8 0.9(2)
C13 C8 C9 C10 -0.1(2)
C7 C8 C9 C10 178.17(14)
C18 N3 C19 C15 0.4(3)
C16 C15 C19 N3 -1.8(2)
C14 C15 C19 N3 178.03(14)
C15 C16 C17 C18 -0.4(3)
C1 C2 C3 C4 1.1(3)
C5 C4 C3 C2 -1.2(3)
C19 N3 C18 C17 1.1(3)
C16 C17 C18 N3 -1.2(3)

_cod_database_fobs_code 1544402
