##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     'SHELXL-2017/1'
_journal_date_recd_electronic     2020-08-07
_journal_date_accepted     2020-09-02
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2020
_journal_volume     76
_journal_issue     10
_journal_page_first     1591
_journal_page_last     1594
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989020012128
_journal_coeditor_code     WM5582
_publ_contact_author_name     'Ropak A. Sheakh Mohamad'
_publ_contact_author_address
;
Salahaddin University, College of Science, Department of Chemistry, Erbil, Iraq
;
_publ_contact_author_email
                    'ropak.shekhmohamad@su.edu.krd, wali.hmd@koyauniversity.org'
_publ_contact_author_fax     '+964 7501191363'
_publ_contact_author_phone     '+964 7501191363'
_publ_section_title
;
Crystal structure and Hirshfeld surface analysis of
(E)-N-(4-propyloxybenzylidene)benzo[d]thiazol-2-amine
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Sheakh Mohamad, Ropak A.' .
;
Salahaddin University, College of Science, Department of Chemistry, Erbil, Iraq
;
    'Hamad, Wali M.' .
;
Koya University, Faculty of Science and Health, Department of Chemistry, Koya,
Iraq
;
    'Aziz, Hashim J.' .
;
Salahaddin University, College of Education, Department of Chemistry, Erbil,
Iraq
;
    'Dege, Necmi' .
;
Ondokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics,
55139, Samsun, Turkey
;
_publ_section_synopsis
;
In the crystal, the molecules are linked by C---H...N and weak C---H...π
hydrogen bonds and very weak π--π stacking interactions. Two-dimensional
fingerprint plots show that the largest contributions to the crystal stability
come from H...H and C...H/H...C interactions.
;
_chemical_name_systematic
;
(E)-N-(4-Propyloxybenzylidene)benzo[d]thiazol-2-amine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H16 N2 O S'
_chemical_formula_sum     'C17 H16 N2 O S'
_chemical_formula_iupac     'C17 H16 N2 O S'
_chemical_formula_weight     296.38
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/c'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     17.2510(10)
_cell_length_b     5.6849(3)
_cell_length_c     17.3101(11)
_cell_angle_alpha     90
_cell_angle_beta     116.958(4)
_cell_angle_gamma     90
_cell_volume     1513.14(16)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9824
_cell_measurement_theta_min     2.36
_cell_measurement_theta_max     28.11
_cell_measurement_temperature     296(2)
_exptl_crystal_description     'plate'
_exptl_crystal_colour     'yellow'
_exptl_crystal_size_max     0.670
_exptl_crystal_size_mid     0.337
_exptl_crystal_size_min     0.040
_exptl_crystal_density_diffrn     1.301
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     624
_exptl_absorpt_coefficient_mu     0.214
_exptl_absorpt_correction_type     integration
_exptl_absorpt_process_details
;
(X-RED32; Stoe & Cie, 2002)
;
_exptl_absorpt_correction_T_min     0.8962
_exptl_absorpt_correction_T_max     0.9829
_diffrn_ambient_temperature     296(2)
_diffrn_source     'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Stoe IPDS 2'
_diffrn_measurement_method     'rotation method'
_diffrn_detector_area_resol_mean     6.67
_diffrn_reflns_number     10315
_diffrn_reflns_av_R_equivalents     0.0482
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_theta_min     2.357
_diffrn_reflns_theta_max     25.999
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -21
_diffrn_reflns_limit_h_max     21
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     19
_refine_special_details     ?
_reflns_number_total     2962
_reflns_number_gt     1950
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0805
_refine_ls_R_factor_gt     0.0453
_refine_ls_wR_factor_gt     0.0882
_refine_ls_wR_factor_ref     0.0990
_refine_ls_goodness_of_fit_ref     0.980
_refine_ls_restrained_S_all     0.980
_refine_ls_number_reflns     2962
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                      'w=1/[σ²(Fo²)+(0.0451P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.140
_refine_diff_density_min     -0.134
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
_computing_data_collection
;
X-AREA (Stoe & Cie, 2002)
;
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2002)
;
_computing_data_reduction
;
X-RED (Stoe & Cie, 2002)
;
_computing_structure_solution
;
SHELXT2017/1 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2017/1 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.18402(4) 0.57314(11) 0.34622(4) 0.0693(2) Uani d 1 . .
    O O1 0.68408(9) 0.4674(3) 0.79162(9) 0.0670(4) Uani d 1 . .
    N N2 0.34892(11) 0.7538(3) 0.44924(11) 0.0594(4) Uani d 1 . .
    N N1 0.25411(11) 0.9575(3) 0.32624(11) 0.0605(4) Uani d 1 . .
    C C7 0.27040(13) 0.7771(4) 0.37623(13) 0.0548(5) Uani d 1 . .
    C C9 0.44990(12) 0.5343(4) 0.57024(12) 0.0536(5) Uani d 1 . .
    C C12 0.60529(13) 0.4773(4) 0.72070(12) 0.0543(5) Uani d 1 . .
    C C8 0.36920(13) 0.5628(4) 0.49215(13) 0.0594(5) Uani d 1 . .
    H H8 0.330649 0.436935 0.472533 0.071 Uiso calc 1 . .
    C C6 0.17124(13) 0.9462(4) 0.25862(13) 0.0574(5) Uani d 1 . .
    C C1 0.12228(13) 0.7506(4) 0.25832(13) 0.0591(5) Uani d 1 . .
    C C10 0.51498(13) 0.7056(4) 0.59654(12) 0.0570(5) Uani d 1 . .
    H H10 0.506190 0.841213 0.563558 0.068 Uiso calc 1 . .
    C C11 0.59124(13) 0.6761(4) 0.67003(13) 0.0581(5) Uani d 1 . .
    H H11 0.634211 0.790845 0.686230 0.070 Uiso calc 1 . .
    C C14 0.46538(14) 0.3363(4) 0.62163(14) 0.0635(6) Uani d 1 . .
    H H14 0.422987 0.219895 0.604920 0.076 Uiso calc 1 . .
    C C15 0.70221(14) 0.2747(4) 0.85021(13) 0.0671(6) Uani d 1 . .
    H H15A 0.700893 0.127967 0.821055 0.081 Uiso calc 1 . .
    H H15B 0.658921 0.266962 0.871337 0.081 Uiso calc 1 . .
    C C13 0.54145(14) 0.3061(4) 0.69666(13) 0.0619(5) Uani d 1 . .
    H H13 0.549857 0.172823 0.730695 0.074 Uiso calc 1 . .
    C C5 0.13532(15) 1.1122(4) 0.19285(14) 0.0718(6) Uani d 1 . .
    H H5 0.167215 1.243665 0.192412 0.086 Uiso calc 1 . .
    C C16 0.79051(15) 0.3130(5) 0.92404(15) 0.0773(7) Uani d 1 . .
    H H16A 0.832723 0.320157 0.901537 0.093 Uiso calc 1 . .
    H H16B 0.805157 0.179131 0.962854 0.093 Uiso calc 1 . .
    C C2 0.03805(15) 0.7197(5) 0.19350(15) 0.0742(6) Uani d 1 . .
    H H2 0.005409 0.589611 0.193574 0.089 Uiso calc 1 . .
    C C3 0.00415(16) 0.8855(5) 0.12943(16) 0.0789(7) Uani d 1 . .
    H H3 -0.052292 0.867632 0.085531 0.095 Uiso calc 1 . .
    C C4 0.05246(17) 1.0798(5) 0.12880(15) 0.0777(7) Uani d 1 . .
    H H4 0.028216 1.189367 0.084265 0.093 Uiso calc 1 . .
    C C17 0.7977(2) 0.5324(5) 0.97463(17) 0.0988(9) Uani d 1 . .
    H H17A 0.790480 0.667237 0.938607 0.148 Uiso calc 1 . .
    H H17B 0.853871 0.538215 1.024129 0.148 Uiso calc 1 . .
    H H17C 0.753332 0.532467 0.993616 0.148 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C1 . 1.731(2) ?
    S1 C7 . 1.770(2) ?
    O1 C12 . 1.358(2) ?
    O1 C15 . 1.428(2) ?
    N2 C8 . 1.272(3) ?
    N2 C7 . 1.378(2) ?
    N1 C7 . 1.288(3) ?
    N1 C6 . 1.379(3) ?
    C9 C14 . 1.384(3) ?
    C9 C10 . 1.397(3) ?
    C9 C8 . 1.444(3) ?
    C12 C11 . 1.383(3) ?
    C12 C13 . 1.385(3) ?
    C8 H8 . 0.9300 ?
    C6 C5 . 1.390(3) ?
    C6 C1 . 1.395(3) ?
    C1 C2 . 1.387(3) ?
    C10 C11 . 1.364(3) ?
    C10 H10 . 0.9300 ?
    C11 H11 . 0.9300 ?
    C14 C13 . 1.376(3) ?
    C14 H14 . 0.9300 ?
    C15 C16 . 1.495(3) ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C13 H13 . 0.9300 ?
    C5 C4 . 1.367(3) ?
    C5 H5 . 0.9300 ?
    C16 C17 . 1.496(3) ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C2 C3 . 1.368(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.387(4) ?
    C3 H3 . 0.9300 ?
    C4 H4 . 0.9300 ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 0.9600 ?
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
    C1 S1 C7 . . 88.68(10) ?
    C12 O1 C15 . . 118.74(16) ?
    C8 N2 C7 . . 120.89(19) ?
    C7 N1 C6 . . 111.07(18) ?
    N1 C7 N2 . . 121.13(18) ?
    N1 C7 S1 . . 115.23(15) ?
    N2 C7 S1 . . 123.60(16) ?
    C14 C9 C10 . . 117.71(18) ?
    C14 C9 C8 . . 121.1(2) ?
    C10 C9 C8 . . 121.2(2) ?
    O1 C12 C11 . . 115.01(17) ?
    O1 C12 C13 . . 125.19(19) ?
    C11 C12 C13 . . 119.79(19) ?
    N2 C8 C9 . . 122.4(2) ?
    N2 C8 H8 . . 118.8 ?
    C9 C8 H8 . . 118.8 ?
    N1 C6 C5 . . 124.7(2) ?
    N1 C6 C1 . . 115.69(19) ?
    C5 C6 C1 . . 119.6(2) ?
    C2 C1 C6 . . 121.0(2) ?
    C2 C1 S1 . . 129.72(19) ?
    C6 C1 S1 . . 109.32(15) ?
    C11 C10 C9 . . 120.7(2) ?
    C11 C10 H10 . . 119.6 ?
    C9 C10 H10 . . 119.6 ?
    C10 C11 C12 . . 120.63(19) ?
    C10 C11 H11 . . 119.7 ?
    C12 C11 H11 . . 119.7 ?
    C13 C14 C9 . . 122.1(2) ?
    C13 C14 H14 . . 118.9 ?
    C9 C14 H14 . . 118.9 ?
    O1 C15 C16 . . 107.79(18) ?
    O1 C15 H15A . . 110.1 ?
    C16 C15 H15A . . 110.1 ?
    O1 C15 H15B . . 110.1 ?
    C16 C15 H15B . . 110.1 ?
    H15A C15 H15B . . 108.5 ?
    C14 C13 C12 . . 119.0(2) ?
    C14 C13 H13 . . 120.5 ?
    C12 C13 H13 . . 120.5 ?
    C4 C5 C6 . . 119.1(2) ?
    C4 C5 H5 . . 120.4 ?
    C6 C5 H5 . . 120.4 ?
    C15 C16 C17 . . 113.8(2) ?
    C15 C16 H16A . . 108.8 ?
    C17 C16 H16A . . 108.8 ?
    C15 C16 H16B . . 108.8 ?
    C17 C16 H16B . . 108.8 ?
    H16A C16 H16B . . 107.7 ?
    C3 C2 C1 . . 118.3(2) ?
    C3 C2 H2 . . 120.8 ?
    C1 C2 H2 . . 120.8 ?
    C2 C3 C4 . . 121.2(2) ?
    C2 C3 H3 . . 119.4 ?
    C4 C3 H3 . . 119.4 ?
    C5 C4 C3 . . 120.8(2) ?
    C5 C4 H4 . . 119.6 ?
    C3 C4 H4 . . 119.6 ?
    C16 C17 H17A . . 109.5 ?
    C16 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C16 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
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
    C6 N1 C7 N2 . . . . -178.59(17) ?
    C6 N1 C7 S1 . . . . -0.9(2) ?
    C8 N2 C7 N1 . . . . -170.83(19) ?
    C8 N2 C7 S1 . . . . 11.7(3) ?
    C1 S1 C7 N1 . . . . 0.44(17) ?
    C1 S1 C7 N2 . . . . 178.05(17) ?
    C15 O1 C12 C11 . . . . 176.51(18) ?
    C15 O1 C12 C13 . . . . -4.3(3) ?
    C7 N2 C8 C9 . . . . -178.31(17) ?
    C14 C9 C8 N2 . . . . 171.56(19) ?
    C10 C9 C8 N2 . . . . -8.4(3) ?
    C7 N1 C6 C5 . . . . -178.5(2) ?
    C7 N1 C6 C1 . . . . 1.1(2) ?
    N1 C6 C1 C2 . . . . -179.90(19) ?
    C5 C6 C1 C2 . . . . -0.3(3) ?
    N1 C6 C1 S1 . . . . -0.7(2) ?
    C5 C6 C1 S1 . . . . 178.91(16) ?
    C7 S1 C1 C2 . . . . 179.3(2) ?
    C7 S1 C1 C6 . . . . 0.16(15) ?
    C14 C9 C10 C11 . . . . 0.6(3) ?
    C8 C9 C10 C11 . . . . -179.48(19) ?
    C9 C10 C11 C12 . . . . -0.8(3) ?
    O1 C12 C11 C10 . . . . 179.34(18) ?
    C13 C12 C11 C10 . . . . 0.1(3) ?
    C10 C9 C14 C13 . . . . 0.5(3) ?
    C8 C9 C14 C13 . . . . -179.47(19) ?
    C12 O1 C15 C16 . . . . -177.16(18) ?
    C9 C14 C13 C12 . . . . -1.2(3) ?
    O1 C12 C13 C14 . . . . -178.23(19) ?
    C11 C12 C13 C14 . . . . 1.0(3) ?
    N1 C6 C5 C4 . . . . 179.4(2) ?
    C1 C6 C5 C4 . . . . -0.2(3) ?
    O1 C15 C16 C17 . . . . 61.6(3) ?
    C6 C1 C2 C3 . . . . 0.3(3) ?
    S1 C1 C2 C3 . . . . -178.68(18) ?
    C1 C2 C3 C4 . . . . 0.1(4) ?
    C6 C5 C4 C3 . . . . 0.6(4) ?
    C2 C3 C4 C5 . . . . -0.6(4) ?
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
    C11 H11 N1 3_676 0.93 2.49 3.362(3) 157.0 yes
    C16 H16A Cg2 3_675 0.97 2.91(2) 3.765(3) 147.0 yes
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_T_min     ?
_shelx_estimated_absorpt_T_max     ?
