#------------------------------------------------------------------------------
#$Date: 2019-12-25 20:48:48 +0100 (Wed 25 de Dec de 2019) $
#$Revision: 245794 $
#$URL: svn://www.crystallography.net/cod/cif/2/31/13/2311324.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_2311324
loop_
_publ_author_name
'Mohamed, Shaaban K.'
'Mague, Joel T.'
'Akkurt, Mehmet'
'Hassan, Alaa A.'
'Abdel-Aziz, Ahmed T'
'Albayati, Mustafa R.'
_publ_section_title
;
 Crystal structure of
 1-(cyclo-pentyl-idene-amino)-3-(prop-2-en-1-yl)thio-urea.
;
_journal_coeditor_code           HB7535
_journal_issue                   'Pt 12'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              o924
_journal_page_last               5
_journal_paper_doi               10.1107/S2056989015021003
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C9 H15 N3 S'
_chemical_formula_moiety         'C9 H15 N3 S'
_chemical_formula_sum            'C9 H15 N3 S'
_chemical_formula_weight         197.30
_chemical_name_systematic
;
1-(Cyclopentylideneamino)-3-(prop-2-en-1-yl)thiourea
;
_space_group_IT_number           76
_space_group_name_Hall           'P 4w'
_space_group_name_H-M_alt        'P 41'
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4w'
_symmetry_space_group_name_H-M   'P 41'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0124(2)
_cell_length_b                   9.0124(2)
_cell_length_c                   12.8200(2)
_cell_measurement_reflns_used    7005
_cell_measurement_temperature    150.(2)
_cell_measurement_theta_max      72.4173
_cell_measurement_theta_min      3.4475
_cell_volume                     1041.28(4)
_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 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0323
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7869
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        72.40
_diffrn_reflns_theta_max         72.41
_diffrn_reflns_theta_min         4.91
_exptl_absorpt_coefficient_mu    2.423
_exptl_absorpt_correction_T_max  0.79
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.102
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.177
_refine_ls_abs_structure_details
;
Flack x determined using 826 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1990
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0412
_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)+(0.0616P)²+0.3211P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1092
_reflns_number_gt                1901
_reflns_number_total             1990
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7535sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1041.28(5)
_cod_database_code               2311324
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -y,x,1/4+z
3 -x,-y,1/2+z
4 y,-x,3/4+z
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S1 0.50830(11) 0.10489(10) 0.51268(7) 0.0404(3) Uani d . 1.000
N N1 0.2886(3) 0.4807(3) 0.5217(2) 0.0312(8) Uani d . 1.000
N N2 0.3701(3) 0.3575(3) 0.5510(2) 0.0325(8) Uani d . 1.000
N N3 0.3362(3) 0.2660(3) 0.3854(2) 0.0357(9) Uani d . 1.000
C C1 0.2584(4) 0.5764(4) 0.5926(3) 0.0293(9) Uani d . 1.000
C C2 0.3050(4) 0.5761(4) 0.7060(3) 0.0339(10) Uani d . 1.000
C C3 0.2402(4) 0.7223(4) 0.7498(3) 0.0362(10) Uani d . 1.000
C C4 0.2242(4) 0.8220(4) 0.6547(3) 0.0389(11) Uani d . 1.000
C C5 0.1737(4) 0.7160(4) 0.5686(3) 0.0359(11) Uani d . 1.000
C C6 0.3975(4) 0.2491(4) 0.4790(3) 0.0331(10) Uani d . 1.000
C C7 0.3533(5) 0.1587(5) 0.3012(3) 0.0430(11) Uani d . 1.000
C C8 0.2503(6) 0.0262(6) 0.3117(4) 0.0617(17) Uani d . 1.000
C C9 0.1462(7) -0.0066(7) 0.2532(5) 0.079(2) Uani d . 1.000
H H2A 0.41450 0.57460 0.71240 0.0410 Uiso c RU 1.000
H H2B 0.26350 0.48910 0.74300 0.0410 Uiso c RU 1.000
H H2C 0.41060 0.34020 0.61480 0.0390 Uiso d RU 1.000
H H3A 0.14260 0.70480 0.78310 0.0430 Uiso c RU 1.000
H H3B 0.30820 0.76700 0.80170 0.0430 Uiso c RU 1.000
H H3C 0.27400 0.34430 0.37540 0.0430 Uiso d RU 1.000
H H4A 0.32000 0.86910 0.63660 0.0470 Uiso c RU 1.000
H H4B 0.14930 0.90050 0.66700 0.0470 Uiso c RU 1.000
H H5A 0.06530 0.69880 0.57190 0.0430 Uiso c RU 1.000
H H5B 0.19970 0.75490 0.49880 0.0430 Uiso c RU 1.000
H H7A 0.45720 0.12310 0.30000 0.0520 Uiso c RU 1.000
H H7B 0.33340 0.20860 0.23380 0.0520 Uiso c RU 1.000
H H8 0.26760 -0.03810 0.36910 0.0740 Uiso c RU 1.000
H H9A 0.12420 0.05410 0.19460 0.0950 Uiso c RU 1.000
H H9B 0.08830 -0.09250 0.26690 0.0950 Uiso c RU 1.000
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
_geom_angle_publ_flag
N2 N1 C1 117.4(3) no
N1 N2 C6 119.1(3) no
C6 N3 C7 123.3(3) no
N1 C1 C2 128.4(3) no
N1 C1 C5 121.7(3) no
C2 C1 C5 109.8(3) no
C1 C2 C3 104.0(3) no
N1 N2 H2C 127.00 no
C6 N2 H2C 114.00 no
C2 C3 C4 104.4(3) no
C6 N3 H3C 118.00 no
C7 N3 H3C 118.00 no
C3 C4 C5 103.8(3) no
C1 C5 C4 102.9(3) no
S1 C6 N2 118.9(3) no
N2 C6 N3 116.9(3) no
S1 C6 N3 124.2(3) no
N3 C7 C8 113.1(3) no
C7 C8 C9 126.7(5) no
C1 C2 H2A 111.00 no
C1 C2 H2B 111.00 no
C3 C2 H2A 111.00 no
C3 C2 H2B 111.00 no
H2A C2 H2B 109.00 no
C2 C3 H3A 111.00 no
C2 C3 H3B 111.00 no
C4 C3 H3A 111.00 no
C4 C3 H3B 111.00 no
H3A C3 H3B 109.00 no
C3 C4 H4A 111.00 no
C3 C4 H4B 111.00 no
C5 C4 H4A 111.00 no
C5 C4 H4B 111.00 no
H4A C4 H4B 109.00 no
C1 C5 H5A 111.00 no
C1 C5 H5B 111.00 no
C4 C5 H5A 111.00 no
C4 C5 H5B 111.00 no
H5A C5 H5B 109.00 no
N3 C7 H7A 109.00 no
N3 C7 H7B 109.00 no
C8 C7 H7A 109.00 no
C8 C7 H7B 109.00 no
H7A C7 H7B 108.00 no
C7 C8 H8 117.00 no
C9 C8 H8 117.00 no
C8 C9 H9A 120.00 no
C8 C9 H9B 120.00 no
H9A C9 H9B 120.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C6 1.695(4) no
N1 N2 1.383(4) no
N1 C1 1.282(5) no
N2 C6 1.367(5) no
N3 C6 1.330(5) no
N3 C7 1.457(5) no
C1 C2 1.513(5) no
C1 C5 1.503(5) no
C2 C3 1.547(5) no
N2 H2C 0.9100 no
C3 C4 1.521(5) no
N3 H3C 0.9100 no
C4 C5 1.529(5) no
C7 C8 1.519(7) no
C8 C9 1.237(8) no
C2 H2A 0.9900 no
C2 H2B 0.9900 no
C3 H3A 0.9900 no
C3 H3B 0.9900 no
C4 H4A 0.9900 no
C4 H4B 0.9900 no
C5 H5A 0.9900 no
C5 H5B 0.9900 no
C7 H7A 0.9900 no
C7 H7B 0.9900 no
C8 H8 0.9500 no
C9 H9A 0.9500 no
C9 H9B 0.9500 no
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
N2 H2C N1 2_655 0.91 2.29 3.194(4) 177 yes
N3 H3C N1 . 0.91 2.25 2.642(4) 106 yes
N3 H3C S1 4_564 0.91 2.49 3.310(3) 151 yes
C3 H3A S1 2_555 0.99 2.86 3.663(4) 139 yes
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
_geom_torsion_publ_flag
C1 N1 N2 C6 176.4(3) no
N2 N1 C1 C2 2.3(5) no
N2 N1 C1 C5 178.5(3) no
N1 N2 C6 S1 175.4(2) no
N1 N2 C6 N3 -3.5(5) no
C7 N3 C6 S1 2.2(5) no
C7 N3 C6 N2 -179.0(3) no
C6 N3 C7 C8 80.2(5) no
N1 C1 C2 C3 177.8(4) no
C5 C1 C2 C3 1.3(4) no
N1 C1 C5 C4 -154.9(3) no
C2 C1 C5 C4 21.9(4) no
C1 C2 C3 C4 -24.2(4) no
C2 C3 C4 C5 38.1(3) no
C3 C4 C5 C1 -36.6(3) no
N3 C7 C8 C9 113.4(6) no
