#------------------------------------------------------------------------------
#$Date: 2015-11-22 04:15:29 +0200 (Sun, 22 Nov 2015) $
#$Revision: 170467 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/13/2241350.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_2241350
loop_
_publ_author_name
'Mague, Joel T.'
'Mohamed, Shaaban K.'
'Akkurt, Mehmet'
'Hassan, Alaa A.'
'Abdel-Aziz, Ahmed T.'
'Albayati, Mustafa R.'
_publ_section_title
;
 Crystal structure of
 3-(prop-2-en-1-yl)-1-{[(1E)-1,2,3,4-tetrahydronaphthalen-1-ylidene]amino}thiourea
;
_journal_coeditor_code           HB7539
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o976
_journal_page_last               o977
_journal_paper_doi               10.1107/S2056989015021076
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C14 H17 N3 S'
_chemical_formula_moiety         'C14 H17 N3 S'
_chemical_formula_sum            'C14 H17 N3 S'
_chemical_formula_weight         259.36
_chemical_name_systematic
3-(Prop-2-en-1-yl)-1-{[(1E)-1,2,3,4-tetrahydronaphthalen-1-ylidene]amino}thiourea
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 91.7940(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6665(2)
_cell_length_b                   8.5788(2)
_cell_length_c                   20.4072(5)
_cell_measurement_reflns_used    8207
_cell_measurement_temperature    150.(2)
_cell_measurement_theta_max      74.4903
_cell_measurement_theta_min      4.3352
_cell_volume                     1341.51(6)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT  (Bruker, 2014)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2012)
;
_computing_publication_material
;
SHELXTL (Bruker, 2014)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXT (Bruker, 2014)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10141
_diffrn_reflns_theta_full        69.000
_diffrn_reflns_theta_max         74.482
_diffrn_reflns_theta_min         4.335
_exptl_absorpt_coefficient_mu    2.015
_exptl_absorpt_correction_T_max  0.73
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.164
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.241
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2687
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0458P)²+0.3454P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0835
_reflns_number_gt                2486
_reflns_number_total             2687
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7539sup1.cif
_cod_data_source_block           I
_cod_database_code               2241350
_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   0.685
_shelx_estimated_absorpt_t_max   0.733
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_occupancy
S S1 0.48923(4) 0.32351(4) 0.80129(2) 0.03037(11) Uani d 1
N N1 0.24491(13) 0.48661(13) 0.73353(5) 0.0280(2) Uani d 1
H H1N 0.2236 0.5554 0.7003 0.034 Uiso d 1
N N2 0.51325(12) 0.47130(12) 0.68903(5) 0.0239(2) Uani d 1
H H2N 0.6272 0.4415 0.6911 0.029 Uiso d 1
N N3 0.44987(12) 0.56539(11) 0.63901(4) 0.0220(2) Uani d 1
C C1 -0.0358(2) 0.27861(18) 0.69916(8) 0.0472(4) Uani d 1
H H1A 0.0572 0.2901 0.6699 0.057 Uiso calc 1
H H1B -0.1320 0.2131 0.6878 0.057 Uiso calc 1
C C2 -0.03150(17) 0.35274(17) 0.75504(7) 0.0348(3) Uani d 1
H H2 -0.1277 0.3373 0.7826 0.042 Uiso calc 1
C C3 0.10929(16) 0.45938(16) 0.78005(6) 0.0299(3) Uani d 1
H H3A 0.0565 0.5606 0.7917 0.036 Uiso calc 1
H H3B 0.1628 0.4143 0.8206 0.036 Uiso calc 1
C C4 0.40678(15) 0.43269(13) 0.73855(5) 0.0234(2) Uani d 1
C C5 0.55646(14) 0.60710(13) 0.59461(5) 0.0203(2) Uani d 1
C C6 0.74503(15) 0.55855(14) 0.59361(6) 0.0249(2) Uani d 1
H H6A 0.7515 0.4483 0.5795 0.030 Uiso calc 1
H H6B 0.7964 0.5655 0.6386 0.030 Uiso calc 1
C C7 0.85274(15) 0.65815(15) 0.54803(6) 0.0265(3) Uani d 1
H H7A 0.8674 0.7639 0.5669 0.032 Uiso calc 1
H H7B 0.9700 0.6114 0.5440 0.032 Uiso calc 1
C C8 0.76392(16) 0.66981(15) 0.48046(6) 0.0279(3) Uani d 1
H H8A 0.8331 0.7386 0.4522 0.033 Uiso calc 1
H H8B 0.7588 0.5652 0.4600 0.033 Uiso calc 1
C C9 0.58186(15) 0.73399(13) 0.48518(5) 0.0235(2) Uani d 1
C C10 0.50909(18) 0.82536(14) 0.43472(6) 0.0293(3) Uani d 1
H H10 0.5748 0.8447 0.3969 0.035 Uiso calc 1
C C11 0.34410(18) 0.88813(14) 0.43851(6) 0.0323(3) Uani d 1
H H11 0.2971 0.9499 0.4036 0.039 Uiso calc 1
C C12 0.24694(17) 0.86062(14) 0.49371(6) 0.0299(3) Uani d 1
H H12 0.1333 0.9037 0.4966 0.036 Uiso calc 1
C C13 0.31603(15) 0.77037(13) 0.54449(6) 0.0244(2) Uani d 1
H H13 0.2494 0.7522 0.5822 0.029 Uiso calc 1
C C14 0.48339(15) 0.70551(13) 0.54080(5) 0.0208(2) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C4 N1 C3 125.63(10)
C4 N1 H1N 115.4
C3 N1 H1N 118.5
C4 N2 N3 119.17(10)
C4 N2 H2N 119.7
N3 N2 H2N 121.0
C5 N3 N2 117.81(10)
C2 C1 H1A 120.0
C2 C1 H1B 120.0
H1A C1 H1B 120.0
C1 C2 C3 126.56(14)
C1 C2 H2 116.7
C3 C2 H2 116.7
N1 C3 C2 113.63(11)
N1 C3 H3A 108.8
C2 C3 H3A 108.8
N1 C3 H3B 108.8
C2 C3 H3B 108.8
H3A C3 H3B 107.7
N1 C4 N2 116.10(10)
N1 C4 S1 125.31(9)
N2 C4 S1 118.58(9)
N3 C5 C14 116.47(10)
N3 C5 C6 124.24(10)
C14 C5 C6 119.26(10)
C5 C6 C7 113.07(10)
C5 C6 H6A 109.0
C7 C6 H6A 109.0
C5 C6 H6B 109.0
C7 C6 H6B 109.0
H6A C6 H6B 107.8
C8 C7 C6 110.73(10)
C8 C7 H7A 109.5
C6 C7 H7A 109.5
C8 C7 H7B 109.5
C6 C7 H7B 109.5
H7A C7 H7B 108.1
C9 C8 C7 110.81(10)
C9 C8 H8A 109.5
C7 C8 H8A 109.5
C9 C8 H8B 109.5
C7 C8 H8B 109.5
H8A C8 H8B 108.1
C10 C9 C14 118.77(11)
C10 C9 C8 120.51(11)
C14 C9 C8 120.71(10)
C11 C10 C9 121.58(12)
C11 C10 H10 119.2
C9 C10 H10 119.2
C10 C11 C12 119.66(11)
C10 C11 H11 120.2
C12 C11 H11 120.2
C13 C12 C11 119.94(12)
C13 C12 H12 120.0
C11 C12 H12 120.0
C12 C13 C14 120.69(11)
C12 C13 H13 119.7
C14 C13 H13 119.7
C13 C14 C9 119.35(10)
C13 C14 C5 120.78(10)
C9 C14 C5 119.87(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C4 1.6928(12)
N1 C4 1.3254(16)
N1 C3 1.4487(16)
N1 H1N 0.9098
N2 C4 1.3597(15)
N2 N3 1.3778(13)
N2 H2N 0.9098
N3 C5 1.2897(15)
C1 C2 1.305(2)
C1 H1A 0.9500
C1 H1B 0.9500
C2 C3 1.4926(19)
C2 H2 0.9500
C3 H3A 0.9900
C3 H3B 0.9900
C5 C14 1.4811(15)
C5 C6 1.5052(16)
C6 C7 1.5249(16)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.5220(16)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.5063(17)
C8 H8A 0.9900
C8 H8B 0.9900
C9 C10 1.3964(17)
C9 C14 1.4042(16)
C10 C11 1.379(2)
C10 H10 0.9500
C11 C12 1.390(2)
C11 H11 0.9500
C12 C13 1.3854(17)
C12 H12 0.9500
C13 C14 1.4027(16)
C13 H13 0.9500
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
N1 H1N N3 . 0.91 2.17 2.6146(13) 109
N1 H1N S1 2_556 0.91 2.82 3.4642(11) 129
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
C4 N2 N3 C5 176.28(10)
C4 N1 C3 C2 -109.16(14)
C1 C2 C3 N1 4.4(2)
C3 N1 C4 N2 179.56(11)
C3 N1 C4 S1 -1.23(18)
N3 N2 C4 N1 1.89(16)
N3 N2 C4 S1 -177.38(8)
N2 N3 C5 C14 178.78(9)
N2 N3 C5 C6 0.54(16)
N3 C5 C6 C7 -163.89(11)
C14 C5 C6 C7 17.91(14)
C5 C6 C7 C8 -50.50(14)
C6 C7 C8 C9 56.66(13)
C7 C8 C9 C10 147.83(11)
C7 C8 C9 C14 -31.02(15)
C14 C9 C10 C11 0.25(17)
C8 C9 C10 C11 -178.62(11)
C9 C10 C11 C12 0.07(18)
C10 C11 C12 C13 -0.07(18)
C11 C12 C13 C14 -0.26(18)
C12 C13 C14 C9 0.58(17)
C12 C13 C14 C5 -179.10(10)
C10 C9 C14 C13 -0.57(16)
C8 C9 C14 C13 178.30(10)
C10 C9 C14 C5 179.12(10)
C8 C9 C14 C5 -2.02(16)
N3 C5 C14 C13 10.37(15)
C6 C5 C14 C13 -171.29(10)
N3 C5 C14 C9 -169.31(10)
C6 C5 C14 C9 9.03(15)

_cod_database_fobs_code 2241350
