#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/85/2218572.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_2218572
loop_
_publ_author_name
'Shan, Shang'
'Wang, Shan-Heng'
'Xu, Ying-Li'
'Xie, Pei-Jin'
'Tian, Yu-Liang'
_publ_section_title
;
 Methyl 3-[(E)-furfurylidene]dithiocarbazate
;
_journal_coeditor_code           XU2417
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o970
_journal_paper_doi               10.1107/S1600536808012506
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C7 H8 N2 O S2'
_chemical_formula_moiety         'C7 H8 N2 O S2'
_chemical_formula_sum            'C7 H8 N2 O S2'
_chemical_formula_weight         200.27
_chemical_melting_point_gt       414
_chemical_melting_point_lt       416
_chemical_name_systematic
;
Methyl 3-[(E)-furfurylidene]dithiocarbazate
;
_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                93.970(14)
_cell_angle_beta                 91.856(12)
_cell_angle_gamma                98.293(12)
_cell_formula_units_Z            2
_cell_length_a                   4.0866(8)
_cell_length_b                   8.8698(12)
_cell_length_c                   12.8453(15)
_cell_measurement_reflns_used    2276
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.0
_cell_volume                     459.21(12)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID IP'
_diffrn_measurement_method       ω
_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  0.030
_diffrn_reflns_av_sigmaI/netI    0.031
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4733
_diffrn_reflns_theta_full        25.2
_diffrn_reflns_theta_max         25.2
_diffrn_reflns_theta_min         1.6
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.532
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.28
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1608
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.039
_refine_ls_R_factor_gt           0.031
_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)+(0.0598P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.092
_refine_ls_wR_factor_ref         0.096
_reflns_number_gt                1349
_reflns_number_total             1608
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2417.cif
_cod_data_source_block           I
_cod_database_code               2218572
_cod_database_fobs_code          2218572
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
S S1 0.20815(13) 0.27619(5) 0.50863(4) 0.0516(2) Uani d . 1
S S2 0.38692(13) 0.20142(5) 0.28541(4) 0.0506(2) Uani d . 1
N N1 0.1859(4) 0.45265(16) 0.35473(12) 0.0464(4) Uani d . 1
H H1 0.1098 0.5149 0.3988 0.056 Uiso calc R 1
N N2 0.2353(4) 0.49265(16) 0.25394(11) 0.0449(4) Uani d . 1
O O1 0.3206(4) 0.60245(14) 0.05809(10) 0.0553(4) Uani d . 1
C C1 0.2537(4) 0.3197(2) 0.38518(14) 0.0407(4) Uani d . 1
C C2 0.4665(5) 0.0393(2) 0.35393(17) 0.0557(5) Uani d . 1
H H2A 0.6311 0.0720 0.4090 0.084 Uiso calc R 1
H H2B 0.5448 -0.0343 0.3062 0.084 Uiso calc R 1
H H2C 0.2659 -0.0063 0.3831 0.084 Uiso calc R 1
C C3 0.1483(5) 0.6216(2) 0.23454(16) 0.0502(5) Uani d . 1
H H3 0.0577 0.6772 0.2875 0.060 Uiso calc R 1
C C4 0.1847(5) 0.6835(2) 0.13501(16) 0.0481(5) Uani d . 1
C C5 0.1076(7) 0.8131(3) 0.09881(19) 0.0685(6) Uani d . 1
H H5 0.0139 0.8886 0.1360 0.082 Uiso calc R 1
C C6 0.1961(6) 0.8126(3) -0.00661(18) 0.0673(6) Uani d . 1
H H6 0.1705 0.8873 -0.0523 0.081 Uiso calc R 1
C C7 0.3227(6) 0.6849(3) -0.02770(17) 0.0608(6) Uani d . 1
H H7 0.4018 0.6557 -0.0920 0.073 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0714(4) 0.0502(3) 0.0359(3) 0.0125(2) 0.0107(2) 0.0105(2)
S2 0.0694(4) 0.0482(3) 0.0378(3) 0.0171(2) 0.0114(2) 0.0072(2)
N1 0.0681(10) 0.0401(8) 0.0326(9) 0.0104(7) 0.0108(7) 0.0056(7)
N2 0.0614(10) 0.0393(8) 0.0352(9) 0.0078(7) 0.0060(7) 0.0077(7)
O1 0.0837(10) 0.0443(7) 0.0418(8) 0.0168(7) 0.0145(7) 0.0112(6)
C1 0.0456(10) 0.0405(9) 0.0345(10) 0.0013(8) 0.0024(8) 0.0026(8)
C2 0.0701(14) 0.0467(11) 0.0534(13) 0.0161(9) 0.0056(10) 0.0087(9)
C3 0.0655(13) 0.0478(11) 0.0390(11) 0.0114(9) 0.0094(9) 0.0051(9)
C4 0.0631(12) 0.0419(10) 0.0419(11) 0.0129(9) 0.0072(9) 0.0076(8)
C5 0.0988(17) 0.0596(13) 0.0577(14) 0.0391(12) 0.0168(12) 0.0165(11)
C6 0.0947(17) 0.0596(13) 0.0544(15) 0.0224(12) 0.0054(12) 0.0278(11)
C7 0.0875(16) 0.0583(12) 0.0393(12) 0.0115(11) 0.0109(10) 0.0173(9)
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
C1 S2 C2 101.98(9)
C1 N1 N2 121.34(16)
C1 N1 H1 119.3
N2 N1 H1 119.3
C3 N2 N1 114.59(16)
C4 O1 C7 106.45(15)
N1 C1 S1 120.76(14)
N1 C1 S2 114.05(13)
S1 C1 S2 125.19(11)
S2 C2 H2A 109.5
S2 C2 H2B 109.5
H2A C2 H2B 109.5
S2 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
N2 C3 C4 122.79(19)
N2 C3 H3 118.6
C4 C3 H3 118.6
C5 C4 O1 109.57(17)
C5 C4 C3 132.1(2)
O1 C4 C3 118.37(16)
C4 C5 C6 106.8(2)
C4 C5 H5 126.6
C6 C5 H5 126.6
C7 C6 C5 106.67(19)
C7 C6 H6 126.7
C5 C6 H6 126.7
C6 C7 O1 110.5(2)
C6 C7 H7 124.8
O1 C7 H7 124.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.6675(18)
S2 C1 1.7500(19)
S2 C2 1.800(2)
N1 N2 1.379(2)
N1 C1 1.331(2)
N1 H1 0.8600
N2 C3 1.284(2)
O1 C4 1.361(2)
O1 C7 1.364(2)
C2 H2A 0.9600
C2 H2B 0.9600
C2 H2C 0.9600
C3 C4 1.430(3)
C3 H3 0.9300
C4 C5 1.344(3)
C5 C6 1.413(3)
C5 H5 0.9300
C6 C7 1.327(4)
C6 H6 0.9300
C7 H7 0.9300
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
N1 H1 S1 2_566 0.86 2.65 3.4892(17) 165 y
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 N1 N2 C3 177.62(17)
N2 N1 C1 S1 177.32(12)
N2 N1 C1 S2 -3.0(2)
C2 S2 C1 N1 178.23(14)
C2 S2 C1 S1 -2.13(15)
N1 N2 C3 C4 179.09(17)
C7 O1 C4 C5 -0.6(2)
C7 O1 C4 C3 179.25(18)
N2 C3 C4 C5 179.2(2)
N2 C3 C4 O1 -0.7(3)
O1 C4 C5 C6 0.7(3)
C3 C4 C5 C6 -179.2(2)
C4 C5 C6 C7 -0.5(3)
C5 C6 C7 O1 0.1(3)
C4 O1 C7 C6 0.3(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4834885
