#------------------------------------------------------------------------------
#$Date: 2015-09-26 05:05:03 +0300 (Sat, 26 Sep 2015) $
#$Revision: 158332 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/10/2241078.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_2241078
loop_
_publ_author_name
'Jotani, Mukesh M.'
'Yeo, Chien Ing'
'Tiekink, Edward R. T.'
_publ_section_title
;
 Crystal structure of 1-(4-methylphenyl)-3-(propan-2-ylideneamino)thiourea
;
_journal_coeditor_code           HB7507
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1236
_journal_page_last               1241
_journal_paper_doi               10.1107/S2056989015017624
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C11 H15 N3 S'
_chemical_formula_moiety         'C11 H15 N3 S'
_chemical_formula_sum            'C11 H15 N3 S'
_chemical_formula_weight         221.32
_chemical_name_systematic
;
1-(4-Methylphenyl)-3-(propan-2-ylideneamino)thiourea
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 102.6900(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7289(13)
_cell_length_b                   7.4341(7)
_cell_length_c                   11.5757(11)
_cell_measurement_reflns_used    1590
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.46
_cell_measurement_theta_min      3.04
_cell_volume                     1152.58(19)
_computing_cell_refinement
;
APEX2 (Bruker, 2008)
;
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012), QMol (Gans & Shalloway,
2001),
DIAMOND (Brandenburg, 2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014/7 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and 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  0.0502
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10739
_diffrn_reflns_theta_full        27.499
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         3.042
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_correction_T_min  0.9704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            light-brown
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       prism
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.267
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2646
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0332P)²+0.7356P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0979
_reflns_number_gt                2052
_reflns_number_total             2646
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7507sup1.cif
_cod_data_source_block           I
_cod_database_code               2241078
_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   0.970
_shelx_estimated_absorpt_t_max   0.992
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'
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 0.14991(3) 0.10760(6) 0.53754(4) 0.01865(13) Uani d 1
N N1 0.17657(11) 0.1754(2) 0.31707(14) 0.0179(3) Uani d 1
H H1N 0.1468(14) 0.175(3) 0.2419(9) 0.023(6) Uiso d 1
N N2 0.01790(11) 0.1178(2) 0.33437(14) 0.0174(3) Uani d 1
H H2N -0.0236(13) 0.073(3) 0.3744(17) 0.032(6) Uiso d 1
N N3 -0.00516(11) 0.1118(2) 0.21071(13) 0.0177(3) Uani d 1
C C1 0.11491(13) 0.1348(2) 0.38949(16) 0.0158(4) Uani d 1
C C2 0.28274(13) 0.1793(2) 0.34532(16) 0.0174(4) Uani d 1
C C3 0.33249(14) 0.0928(3) 0.26883(17) 0.0218(4) Uani d 1
H H3 0.2955 0.0313 0.2013 0.026 Uiso calc 1
C C4 0.43587(14) 0.0956(3) 0.29054(17) 0.0240(4) Uani d 1
H H4 0.4688 0.0357 0.2374 0.029 Uiso calc 1
C C5 0.49234(14) 0.1841(3) 0.38822(17) 0.0218(4) Uani d 1
C C6 0.44118(15) 0.2713(3) 0.46362(18) 0.0240(4) Uani d 1
H H6 0.4781 0.3329 0.5311 0.029 Uiso calc 1
C C7 0.33772(14) 0.2703(3) 0.44266(17) 0.0221(4) Uani d 1
H H7 0.3046 0.3319 0.4949 0.027 Uiso calc 1
C C8 0.60488(15) 0.1844(3) 0.4134(2) 0.0316(5) Uani d 1
H H8A 0.6299 0.3006 0.4475 0.047 Uiso calc 1
H H8B 0.6271 0.1650 0.3395 0.047 Uiso calc 1
H H8C 0.6307 0.0880 0.4695 0.047 Uiso calc 1
C C9 -0.09645(13) 0.1333(2) 0.15732(16) 0.0163(4) Uani d 1
C C10 -0.18214(14) 0.1717(3) 0.21420(17) 0.0220(4) Uani d 1
H H10A -0.1571 0.2260 0.2922 0.033 Uiso calc 1
H H10B -0.2169 0.0592 0.2233 0.033 Uiso calc 1
H H10C -0.2285 0.2549 0.1643 0.033 Uiso calc 1
C C11 -0.11855(14) 0.1185(3) 0.02523(16) 0.0201(4) Uani d 1
H H11A -0.0561 0.1262 -0.0024 0.030 Uiso calc 1
H H11B -0.1631 0.2166 -0.0096 0.030 Uiso calc 1
H H11C -0.1509 0.0028 0.0011 0.030 Uiso calc 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
C1 N1 C2 127.79(16)
C1 N1 H1N 113.3(14)
C2 N1 H1N 117.3(14)
C1 N2 N3 117.72(15)
C1 N2 H2N 118.4(15)
N3 N2 H2N 120.2(15)
C9 N3 N2 117.91(15)
N1 C1 N2 114.54(16)
N1 C1 S1 125.45(14)
N2 C1 S1 120.00(14)
C7 C2 C3 119.20(17)
C7 C2 N1 122.98(17)
C3 C2 N1 117.79(17)
C4 C3 C2 120.30(18)
C4 C3 H3 119.9
C2 C3 H3 119.9
C3 C4 C5 121.42(18)
C3 C4 H4 119.3
C5 C4 H4 119.3
C4 C5 C6 117.52(17)
C4 C5 C8 121.55(18)
C6 C5 C8 120.92(18)
C7 C6 C5 121.69(18)
C7 C6 H6 119.2
C5 C6 H6 119.2
C2 C7 C6 119.87(18)
C2 C7 H7 120.1
C6 C7 H7 120.1
C5 C8 H8A 109.5
C5 C8 H8B 109.5
H8A C8 H8B 109.5
C5 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
N3 C9 C11 116.21(16)
N3 C9 C10 126.34(17)
C11 C9 C10 117.46(16)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C9 C11 H11A 109.5
C9 C11 H11B 109.5
H11A C11 H11B 109.5
C9 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.6873(18)
N1 C1 1.350(2)
N1 C2 1.422(2)
N1 H1N 0.876(9)
N2 C1 1.350(2)
N2 N3 1.397(2)
N2 H2N 0.875(9)
N3 C9 1.280(2)
C2 C7 1.387(3)
C2 C3 1.389(3)
C3 C4 1.386(3)
C3 H3 0.9500
C4 C5 1.388(3)
C4 H4 0.9500
C5 C6 1.395(3)
C5 C8 1.508(3)
C6 C7 1.387(3)
C6 H6 0.9500
C7 H7 0.9500
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 C11 1.496(2)
C9 C10 1.496(3)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
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 . 0.876(11) 2.091(19) 2.572(2) 113.7(14)
N1 H1N S1 4_565 0.876(11) 2.873(15) 3.5618(17) 136.7(17)
N2 H2N S1 3_556 0.875(19) 2.57(2) 3.4373(16) 169.0(19)
C8 H8C Cg1 3_656 0.98 2.81 3.716(2) 154
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
C1 N2 N3 C9 -165.78(16)
C2 N1 C1 N2 -171.29(17)
C2 N1 C1 S1 9.3(3)
N3 N2 C1 N1 11.0(2)
N3 N2 C1 S1 -169.57(12)
C1 N1 C2 C7 -50.1(3)
C1 N1 C2 C3 132.2(2)
C7 C2 C3 C4 0.8(3)
N1 C2 C3 C4 178.60(17)
C2 C3 C4 C5 0.0(3)
C3 C4 C5 C6 -0.4(3)
C3 C4 C5 C8 178.82(19)
C4 C5 C6 C7 0.0(3)
C8 C5 C6 C7 -179.16(18)
C3 C2 C7 C6 -1.1(3)
N1 C2 C7 C6 -178.81(17)
C5 C6 C7 C2 0.7(3)
N2 N3 C9 C11 -177.62(15)
N2 N3 C9 C10 2.4(3)

_cod_database_fobs_code 2241078
