#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/50/2215064.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_2215064
loop_
_publ_author_name
'Jing, Zuo-Liang'
'Yu, Ming'
'Chen, Xin'
_publ_section_title
;
 (E)-N'-(3-Thienylmethylene)furan-2-carbohydrazide
;
_journal_coeditor_code           CI2444
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3899
_journal_page_last               o3899
_journal_paper_doi               10.1107/S1600536807041293
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C10 H8 N2 O2 S'
_chemical_formula_moiety         'C10 H8 N2 O2 S'
_chemical_formula_sum            'C10 H8 N2 O2 S'
_chemical_formula_weight         220.24
_chemical_name_systematic
;
(E)-N'-(3-Thienylmethylene)furan-2-carbohydrazide
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1150(15)
_cell_length_b                   4.7969(7)
_cell_length_c                   20.033(3)
_cell_measurement_reflns_used    3232
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.18
_cell_measurement_theta_min      4.03
_cell_volume                     972.0(2)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1999)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4486
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.03
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.311
_exptl_absorpt_correction_T_max  0.9461
_exptl_absorpt_correction_T_min  0.9291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.136
_refine_ls_abs_structure_details 'Flack (1983), with 811 Friedel pairs'
_refine_ls_abs_structure_Flack   0.04(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1694
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0230
_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)+(0.0391P)²+0.0578P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0624
_refine_ls_wR_factor_ref         0.0646
_reflns_number_gt                1616
_reflns_number_total             1694
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2444.cif
_cod_data_source_block           I
_cod_database_code               2215064
_cod_database_fobs_code          2215064
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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
S S1 0.22029(5) 1.02129(9) 0.32352(3) 0.04200(14) Uani d . 1
O O1 -0.15782(12) 0.0679(3) 0.10495(7) 0.0473(4) Uani d . 1
O O2 -0.11967(13) -0.2927(3) 0.00357(7) 0.0547(4) Uani d . 1
N N1 0.04650(14) 0.3353(3) 0.16534(7) 0.0352(3) Uani d . 1
N N2 0.06307(14) 0.1461(3) 0.11429(8) 0.0352(3) Uani d D 1
C C1 0.05895(18) 0.9185(4) 0.32440(11) 0.0412(4) Uani d . 1
H H1 -0.0038 0.9854 0.3543 0.049 Uiso calc R 1
C C2 0.03343(17) 0.7284(4) 0.27648(10) 0.0398(4) Uani d . 1
H H2 -0.0493 0.6488 0.2696 0.048 Uiso calc R 1
C C3 0.14683(17) 0.6629(4) 0.23753(9) 0.0324(4) Uani d . 1
C C4 0.2551(2) 0.8089(4) 0.25789(10) 0.0383(4) Uani d . 1
H H4 0.3382 0.7940 0.2383 0.046 Uiso calc R 1
C C5 0.1512(2) 0.4638(4) 0.18335(9) 0.0360(4) Uani d . 1
H H5 0.2307 0.4291 0.1615 0.043 Uiso calc R 1
C C6 -0.04417(19) 0.0210(4) 0.08752(9) 0.0341(4) Uani d . 1
C C7 -0.01324(16) -0.1763(4) 0.03386(9) 0.0348(4) Uani d . 1
C C8 0.0966(2) -0.2736(5) 0.00599(11) 0.0535(6) Uani d . 1
H H8 0.1827 -0.2267 0.0177 0.064 Uiso calc R 1
C C9 0.0584(2) -0.4613(5) -0.04464(12) 0.0536(6) Uani d . 1
H H9 0.1139 -0.5610 -0.0729 0.064 Uiso calc R 1
C C10 -0.0714(3) -0.4667(5) -0.04373(12) 0.0538(5) Uani d . 1
H H10 -0.1232 -0.5756 -0.0718 0.065 Uiso calc R 1
H H2A 0.1439(12) 0.100(5) 0.1005(10) 0.043(6) Uiso d D 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 0.0360(2) 0.0452(3) 0.0448(2) -0.00471(19) -0.0011(2) -0.0056(2)
O1 0.0262(7) 0.0623(9) 0.0533(8) 0.0012(6) 0.0024(6) -0.0137(7)
O2 0.0331(7) 0.0682(10) 0.0629(9) -0.0067(6) -0.0010(7) -0.0236(8)
N1 0.0298(7) 0.0381(9) 0.0378(8) 0.0020(6) -0.0006(6) -0.0029(7)
N2 0.0256(7) 0.0403(9) 0.0397(8) 0.0018(7) 0.0017(6) -0.0063(7)
C1 0.0333(10) 0.0482(10) 0.0422(9) 0.0001(7) 0.0064(10) 0.0007(11)
C2 0.0291(9) 0.0429(10) 0.0475(11) -0.0016(8) 0.0014(8) -0.0022(9)
C3 0.0268(9) 0.0334(9) 0.0372(10) 0.0013(7) 0.0002(7) 0.0042(8)
C4 0.0299(9) 0.0403(10) 0.0445(10) -0.0010(8) 0.0047(7) -0.0001(8)
C5 0.0293(9) 0.0382(10) 0.0407(10) 0.0023(7) 0.0016(8) 0.0021(8)
C6 0.0294(12) 0.0367(10) 0.0362(10) 0.0005(7) 0.0005(7) 0.0035(7)
C7 0.0309(9) 0.0367(9) 0.0367(9) -0.0035(7) -0.0036(7) 0.0029(8)
C8 0.0283(10) 0.0697(15) 0.0624(13) 0.0015(9) -0.0026(9) -0.0237(11)
C9 0.0418(13) 0.0604(13) 0.0585(13) 0.0018(9) 0.0065(10) -0.0197(12)
C10 0.0513(13) 0.0544(12) 0.0558(13) -0.0036(10) -0.0070(11) -0.0190(11)
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
C4 S1 C1 91.90(10)
C10 O2 C7 106.30(16)
C5 N1 N2 115.26(15)
C6 N2 N1 119.32(15)
C6 N2 H2A 120.3(15)
N1 N2 H2A 120.3(15)
C2 C1 S1 111.79(15)
C2 C1 H1 124.1
S1 C1 H1 124.1
C1 C2 C3 112.67(17)
C1 C2 H2 123.7
C3 C2 H2 123.7
C4 C3 C2 111.75(16)
C4 C3 C5 122.64(18)
C2 C3 C5 125.60(17)
C3 C4 S1 111.89(15)
C3 C4 H4 124.1
S1 C4 H4 124.1
N1 C5 C3 120.34(18)
N1 C5 H5 119.8
C3 C5 H5 119.8
O1 C6 N2 124.07(17)
O1 C6 C7 121.93(17)
N2 C6 C7 113.98(16)
C8 C7 O2 109.34(17)
C8 C7 C6 135.53(17)
O2 C7 C6 115.13(15)
C7 C8 C9 107.30(18)
C7 C8 H8 126.3
C9 C8 H8 126.3
C10 C9 C8 106.1(2)
C10 C9 H9 127.0
C8 C9 H9 127.0
C9 C10 O2 111.0(2)
C9 C10 H10 124.5
O2 C10 H10 124.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C4 1.7003(19)
S1 C1 1.7050(19)
O1 C6 1.222(2)
O2 C10 1.354(3)
O2 C7 1.356(2)
N1 C5 1.277(2)
N1 N2 1.378(2)
N2 C6 1.351(2)
N2 H2A 0.891(9)
C1 C2 1.349(3)
C1 H1 0.93
C2 C3 1.423(2)
C2 H2 0.93
C3 C4 1.363(3)
C3 C5 1.446(3)
C4 H4 0.93
C5 H5 0.93
C6 C7 1.466(3)
C7 C8 1.328(3)
C8 C9 1.410(3)
C8 H8 0.93
C9 C10 1.313(3)
C9 H9 0.93
C10 H10 0.93
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 H2A O1 3_555 0.891(9) 2.163(12) 3.010(2) 158(2) yes
C1 H1 S1 3_475 0.93 2.86 3.438(2) 122 yes
C8 H8 O1 3_555 0.93 2.50 3.328(3) 149 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
C5 N1 N2 C6 -173.46(17)
C4 S1 C1 C2 0.24(17)
S1 C1 C2 C3 -0.1(2)
C1 C2 C3 C4 -0.1(2)
C1 C2 C3 C5 178.91(18)
C2 C3 C4 S1 0.3(2)
C5 C3 C4 S1 -178.77(15)
C1 S1 C4 C3 -0.29(15)
N2 N1 C5 C3 -178.56(15)
C4 C3 C5 N1 -178.84(17)
C2 C3 C5 N1 2.3(3)
N1 N2 C6 O1 1.2(3)
N1 N2 C6 C7 -179.80(14)
C10 O2 C7 C8 0.4(2)
C10 O2 C7 C6 -179.86(17)
O1 C6 C7 C8 -177.7(2)
N2 C6 C7 C8 3.3(3)
O1 C6 C7 O2 2.6(3)
N2 C6 C7 O2 -176.41(15)
O2 C7 C8 C9 0.1(3)
C6 C7 C8 C9 -179.7(2)
C7 C8 C9 C10 -0.5(3)
C8 C9 C10 O2 0.7(3)
C7 O2 C10 C9 -0.7(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4780974
