#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/59/2235927.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_2235927
loop_
_publ_author_name
'Abduelftah, Halema Shaban'
'Ali, Amna Qasem'
'Eltayeb, Naser Eltaher'
'Teoh, Siang Guan'
'Fun, Hoong-Kun'
_publ_section_title
;
 (E)-N-Ethyl-2-[(E)-3-(hydroxyimino)butan-2-ylidene]hydrazinecarbothioamide
;
_journal_coeditor_code           NG5276
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2552
_journal_paper_doi               10.1107/S1600536812028632
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C7 H14 N4 O S'
_chemical_formula_moiety         'C7 H14 N4 O S'
_chemical_formula_sum            'C7 H14 N4 O S'
_chemical_formula_weight         202.28
_chemical_name_systematic
;
(E)-N-Ethyl-2-[(E)-3-(hydroxyimino)butan-2-
ylidene]hydrazinecarbothioamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                71.3090(10)
_cell_angle_beta                 76.3180(10)
_cell_angle_gamma                86.4200(10)
_cell_formula_units_Z            2
_cell_length_a                   5.7065(2)
_cell_length_b                   9.0632(3)
_cell_length_c                   10.7109(4)
_cell_measurement_reflns_used    8235
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      35.10
_cell_measurement_theta_min      3.60
_cell_volume                     509.80(3)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEXII 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  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15442
_diffrn_reflns_theta_full        34.00
_diffrn_reflns_theta_max         34.00
_diffrn_reflns_theta_min         2.61
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  0.9791
_exptl_absorpt_correction_T_min  0.8543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.327
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         4093
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0317
_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)+(0.0432P)²+0.1608P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0933
_reflns_number_gt                3648
_reflns_number_total             4093
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ng5276.cif
_cod_data_source_block           I
_cod_database_code               2235927
_cod_database_fobs_code          2235927
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
S S1 0.44242(4) 0.52051(3) 0.69791(2) 0.02043(7) Uani d . 1 1
O O1 1.61220(13) 1.04092(8) 0.11132(7) 0.02309(14) Uani d . 1 1
H H1O1 1.6452 1.0633 0.0256 0.035 Uiso d R 1 1
N N1 1.41316(13) 0.94009(9) 0.15010(7) 0.01695(13) Uani d . 1 1
N N2 1.01528(13) 0.74755(9) 0.45088(7) 0.01587(13) Uani d . 1 1
N N3 0.81401(13) 0.65358(9) 0.50040(7) 0.01734(13) Uani d . 1 1
H H1N3 0.7419 0.6218 0.4504 0.021 Uiso d R 1 1
N N4 0.82678(13) 0.66298(9) 0.71029(7) 0.01754(13) Uani d . 1 1
H H1N4 0.9652 0.7085 0.6662 0.021 Uiso d R 1 1
C C1 1.41628(18) 0.94145(12) 0.37977(9) 0.02285(17) Uani d . 1 1
H H1A 1.5830 0.9797 0.3405 0.034 Uiso calc R 1 1
H H1B 1.4111 0.8518 0.4613 0.034 Uiso calc R 1 1
H H1C 1.3154 1.0244 0.4035 0.034 Uiso calc R 1 1
C C2 1.32385(15) 0.89332(10) 0.27889(8) 0.01613(14) Uani d . 1 1
C C3 1.11201(15) 0.78830(10) 0.32272(8) 0.01645(14) Uani d . 1 1
C C4 1.02391(19) 0.73958(13) 0.22066(9) 0.0260(2) Uani d . 1 1
H H4A 0.9612 0.6324 0.2616 0.039 Uiso calc R 1 1
H H4B 1.1576 0.7453 0.1425 0.039 Uiso calc R 1 1
H H4C 0.8953 0.8091 0.1911 0.039 Uiso calc R 1 1
C C5 0.70823(14) 0.61747(10) 0.63536(8) 0.01525(13) Uani d . 1 1
C C6 0.73697(16) 0.63713(11) 0.85512(8) 0.01993(15) Uani d . 1 1
H H6A 0.7165 0.5240 0.9036 0.024 Uiso calc R 1 1
H H6B 0.5777 0.6864 0.8714 0.024 Uiso calc R 1 1
C C7 0.91280(18) 0.70594(12) 0.90870(10) 0.02417(18) Uani d . 1 1
H H7A 0.8508 0.6882 1.0059 0.036 Uiso calc R 1 1
H H7B 0.9315 0.8181 0.8612 0.036 Uiso calc R 1 1
H H7C 1.0696 0.6559 0.8936 0.036 Uiso calc R 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
N1 O1 H1O1 101.9
C2 N1 O1 113.41(7)
C3 N2 N3 118.88(7)
C5 N3 N2 117.92(7)
C5 N3 H1N3 117.7
N2 N3 H1N3 124.1
C5 N4 C6 123.53(7)
C5 N4 H1N4 114.6
C6 N4 H1N4 121.9
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N1 C2 C3 114.67(7)
N1 C2 C1 124.68(7)
C3 C2 C1 120.63(7)
N2 C3 C2 114.69(7)
N2 C3 C4 125.37(8)
C2 C3 C4 119.93(7)
C3 C4 H4A 109.5
C3 C4 H4B 109.5
H4A C4 H4B 109.5
C3 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
N4 C5 N3 116.43(7)
N4 C5 S1 123.74(6)
N3 C5 S1 119.83(6)
N4 C6 C7 110.08(7)
N4 C6 H6A 109.6
C7 C6 H6A 109.6
N4 C6 H6B 109.6
C7 C6 H6B 109.6
H6A C6 H6B 108.2
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C5 1.6823(8)
O1 N1 1.4004(9)
O1 H1O1 0.8499
N1 C2 1.2891(10)
N2 C3 1.2913(10)
N2 N3 1.3676(10)
N3 C5 1.3674(10)
N3 H1N3 0.8699
N4 C5 1.3326(10)
N4 C6 1.4594(11)
N4 H1N4 0.8699
C1 C2 1.4955(12)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 C3 1.4753(11)
C3 C4 1.4966(12)
C4 H4A 0.9800
C4 H4B 0.9800
C4 H4C 0.9800
C6 C7 1.5182(13)
C6 H6A 0.9900
C6 H6B 0.9900
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 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
_geom_hbond_publ_flag
O1 H1O1 N1 2_875 0.8500 2.0000 2.7876(10) 154.00 yes
N3 H1N3 S1 2_666 0.8700 2.7500 3.6124(8) 171.00 yes
N4 H1N4 N2 . 0.8700 2.1700 2.6055(10) 111.00 yes
C1 H1A O1 . 0.9800 2.3000 2.6970(11) 103.00 yes
C4 H4A S1 2_666 0.9800 2.6400 3.4302(12) 138.00 yes
C4 H4B N1 . 0.9800 2.3900 2.7636(14) 102.00 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
C3 N2 N3 C5 -177.16(8)
O1 N1 C2 C3 179.32(7)
O1 N1 C2 C1 0.93(13)
N3 N2 C3 C2 178.30(7)
N3 N2 C3 C4 -0.76(14)
N1 C2 C3 N2 -176.75(8)
C1 C2 C3 N2 1.71(12)
N1 C2 C3 C4 2.37(13)
C1 C2 C3 C4 -179.18(9)
C6 N4 C5 N3 178.54(8)
C6 N4 C5 S1 -1.47(13)
N2 N3 C5 N4 -7.33(12)
N2 N3 C5 S1 172.68(6)
C5 N4 C6 C7 -178.86(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657992
