#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/69/2226914.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_2226914
loop_
_publ_author_name
'Li, Yu-Feng'
'Jian, Fang-Fang'
_publ_section_title
;
 (E)-N'-[4-(Methylsulfanyl)benzylidene]furan-2-carbohydrazide
 monohydrate
;
_journal_coeditor_code           HB5554
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2157
_journal_paper_doi               10.1107/S1600536810028655
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H14 N2 O3 S'
_chemical_formula_moiety         'C13 H14 N2 O3 S'
_chemical_formula_sum            'C13 H14 N2 O3 S'
_chemical_formula_weight         278.32
_chemical_name_systematic
;
(E)-N'-[4-(Methylsulfanyl)benzylidene]furan-2-carbohydrazide
monohydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.96(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.7065(9)
_cell_length_b                   12.142(2)
_cell_length_c                   23.979(5)
_cell_measurement_reflns_used    1095
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.50
_cell_measurement_theta_min      3.05
_cell_volume                     1369.5(4)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'phi and omega 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  0.0928
_diffrn_reflns_av_sigmaI/netI    0.0849
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10766
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.249
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.807
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2536
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.807
_refine_ls_R_factor_all          0.1375
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1720
_reflns_number_gt                1095
_reflns_number_total             2536
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5554.cif
_cod_data_source_block           I
_cod_original_cell_volume        1369.6(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226914
_cod_database_fobs_code          2226914
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C5 0.1858(6) 0.6495(3) 0.26977(12) 0.0476(8) Uani d . 1 . .
N N2 0.5006(6) 0.6551(2) 0.19538(11) 0.0543(7) Uani d . 1 . .
C C4 -0.0079(6) 0.5827(3) 0.30142(12) 0.0469(8) Uani d . 1 . .
O O2 -0.0668(5) 0.47801(18) 0.28399(9) 0.0576(7) Uani d . 1 . .
C C6 0.6577(7) 0.5956(3) 0.16494(13) 0.0544(9) Uani d . 1 . .
H H6A 0.6664 0.5200 0.1709 0.065 Uiso calc R 1 . .
C C1 -0.3067(8) 0.5097(3) 0.35996(15) 0.0695(11) Uani d . 1 . .
H H1A -0.4258 0.5003 0.3898 0.083 Uiso calc R 1 . .
C C2 -0.2512(7) 0.4347(3) 0.32055(14) 0.0647(10) Uani d . 1 . .
H H2B -0.3273 0.3641 0.3186 0.078 Uiso calc R 1 . .
C C8 1.0074(7) 0.5792(3) 0.09165(14) 0.0686(11) Uani d . 1 . .
H H8A 1.0343 0.5060 0.1020 0.082 Uiso calc R 1 . .
C C3 -0.1508(8) 0.6049(3) 0.34769(14) 0.0620(10) Uani d . 1 . .
H H3A -0.1473 0.6705 0.3677 0.074 Uiso calc R 1 . .
O O1 0.2107(5) 0.7491(2) 0.27923(10) 0.0628(7) Uani d . 1 . .
C C7 0.8238(7) 0.6447(3) 0.12095(12) 0.0541(9) Uani d . 1 . .
N N1 0.3328(5) 0.5959(2) 0.23110(10) 0.0512(7) Uani d . 1 . .
H H1B 0.3227 0.5254 0.2285 0.061 Uiso calc R 1 . .
C C12 0.7927(8) 0.7535(3) 0.10515(17) 0.0740(11) Uani d . 1 . .
H H12A 0.6732 0.7994 0.1247 0.089 Uiso calc R 1 . .
C C11 0.9370(9) 0.7947(4) 0.06065(17) 0.0823(12) Uani d . 1 . .
H H11A 0.9137 0.8682 0.0507 0.099 Uiso calc R 1 . .
C C10 1.1155(8) 0.7288(4) 0.03055(16) 0.0765(12) Uani d . 1 . .
C C9 1.1526(8) 0.6220(4) 0.04680(16) 0.0809(13) Uani d . 1 . .
H H9A 1.2764 0.5771 0.0277 0.097 Uiso calc R 1 . .
O O3 0.7049(8) 0.8706(2) 0.30372(13) 0.0682(8) Uani d . 1 . .
S S1 1.2735(3) 0.79024(15) -0.02691(5) 0.1234(7) Uani d . 1 . .
C C13 1.4598(13) 0.6810(6) -0.0588(2) 0.161(3) Uani d . 1 . .
H H13A 1.5531 0.7084 -0.0910 0.241 Uiso calc R 1 . .
H H13B 1.3280 0.6242 -0.0700 0.241 Uiso calc R 1 . .
H H13C 1.5989 0.6515 -0.0327 0.241 Uiso calc R 1 . .
H H3B 0.857(12) 0.841(4) 0.2908(19) 0.12(2) Uiso d . 1 . .
H H3C 0.602(17) 0.833(7) 0.288(3) 0.21(4) Uiso 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 0.0033 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C5 N1 . . 123.6(3) ?
O1 C5 C4 . . 120.5(3) ?
N1 C5 C4 . . 115.9(3) ?
C6 N2 N1 . . 114.4(3) ?
C3 C4 O2 . . 109.7(3) ?
C3 C4 C5 . . 131.2(3) ?
O2 C4 C5 . . 119.0(3) ?
C2 O2 C4 . . 106.9(2) ?
N2 C6 C7 . . 121.0(3) ?
N2 C6 H6A . . 119.5 ?
C7 C6 H6A . . 119.5 ?
C2 C1 C3 . . 107.1(3) ?
C2 C1 H1A . . 126.4 ?
C3 C1 H1A . . 126.4 ?
C1 C2 O2 . . 109.6(3) ?
C1 C2 H2B . . 125.2 ?
O2 C2 H2B . . 125.2 ?
C7 C8 C9 . . 120.6(4) ?
C7 C8 H8A . . 119.7 ?
C9 C8 H8A . . 119.7 ?
C4 C3 C1 . . 106.7(3) ?
C4 C3 H3A . . 126.7 ?
C1 C3 H3A . . 126.7 ?
C12 C7 C8 . . 118.2(3) ?
C12 C7 C6 . . 122.3(3) ?
C8 C7 C6 . . 119.4(3) ?
C5 N1 N2 . . 119.6(3) ?
C5 N1 H1B . . 120.2 ?
N2 N1 H1B . . 120.2 ?
C11 C12 C7 . . 120.6(4) ?
C11 C12 H12A . . 119.7 ?
C7 C12 H12A . . 119.7 ?
C12 C11 C10 . . 121.3(4) ?
C12 C11 H11A . . 119.4 ?
C10 C11 H11A . . 119.4 ?
C9 C10 C11 . . 118.4(4) ?
C9 C10 S1 . . 125.1(4) ?
C11 C10 S1 . . 116.5(4) ?
C10 C9 C8 . . 120.9(4) ?
C10 C9 H9A . . 119.6 ?
C8 C9 H9A . . 119.6 ?
H3B O3 H3C . . 96(6) ?
C10 S1 C13 . . 104.4(3) ?
S1 C13 H13A . . 109.5 ?
S1 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
S1 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C5 O1 . 1.235(4) ?
C5 N1 . 1.344(4) ?
C5 C4 . 1.454(4) ?
N2 C6 . 1.280(4) ?
N2 N1 . 1.385(3) ?
C4 C3 . 1.344(4) ?
C4 O2 . 1.364(4) ?
O2 C2 . 1.360(4) ?
C6 C7 . 1.461(4) ?
C6 H6A . 0.9300 ?
C1 C2 . 1.344(5) ?
C1 C3 . 1.406(5) ?
C1 H1A . 0.9300 ?
C2 H2B . 0.9300 ?
C8 C7 . 1.384(4) ?
C8 C9 . 1.394(5) ?
C8 H8A . 0.9300 ?
C3 H3A . 0.9300 ?
C7 C12 . 1.380(5) ?
N1 H1B . 0.8600 ?
C12 C11 . 1.378(5) ?
C12 H12A . 0.9300 ?
C11 C10 . 1.381(6) ?
C11 H11A . 0.9300 ?
C10 C9 . 1.364(6) ?
C10 S1 . 1.754(4) ?
C9 H9A . 0.9300 ?
O3 H3B . 0.87(5) ?
O3 H3C . 0.75(8) ?
S1 C13 . 1.777(6) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
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 H1B O2 . 0.86 2.37 2.713(3) 104
N1 H1B O3 2_645 0.86 2.03 2.864(4) 162
O3 H3B O1 1_655 0.87(5) 2.03(6) 2.878(4) 165(4)
O3 H3C O1 . 0.76(8) 2.11(8) 2.800(4) 152(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656155
