#------------------------------------------------------------------------------
#$Date: 2025-08-19 20:17:10 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301807 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/17/2241740.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_2241740
loop_
_publ_author_name
'Cardoso, Laura N. F.'
'Nogueira, Thais C. M.'
'Wardell, James L.'
'Wardell, Solange M. S. V.'
'de Souza, Marcus V. N.'
'Jotani, Mukesh M.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 N'-[(1E)-(5-Nitrofuran-2-yl)methylidene]thiophene-2-carbohydrazide:
 crystal structure and Hirshfeld surface analysis
;
_journal_coeditor_code           HB7593
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1025
_journal_page_last               1031
_journal_paper_doi               10.1107/S2056989016009968
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C10 H7 N3 O4 S'
_chemical_formula_moiety         'C10 H7 N3 O4 S'
_chemical_formula_sum            'C10 H7 N3 O4 S'
_chemical_formula_weight         265.25
_chemical_name_systematic
N'-[(1E)-(5-Nitrofuran-2-yl)methylidene]thiophene-2-carbohydrazide
_space_group_crystal_system      tetragonal
_space_group_IT_number           110
_space_group_name_Hall           'I 4bw -2c'
_space_group_name_H-M_alt        'I 41 c d'
_symmetry_space_group_name_Hall  'I 4bw -2c'
_symmetry_space_group_name_H-M   'I 41 c d'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   17.4072(16)
_cell_length_b                   17.4072(16)
_cell_length_c                   14.4881(10)
_cell_measurement_reflns_used    9311
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.3
_cell_volume                     4390.0(6)
_computing_cell_refinement
;
CrystalClear-SM Expert (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert (Rigaku, 2011)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012), QMol (Gans & Shalloway,
2001) and
DIAMOND (Brandenburg, 2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10325
_diffrn_reflns_theta_full        27.467
_diffrn_reflns_theta_max         27.467
_diffrn_reflns_theta_min         3.263
_exptl_absorpt_coefficient_mu    0.306
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrystalClear-SM Expert; Rigaku, 2011)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_description       rod
_exptl_crystal_F_000             2176
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.308
_refine_ls_abs_structure_details
;
Flack x determined using 766 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al. 2013)
;
_refine_ls_abs_structure_Flack   -0.06(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2292
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0449
_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)+(0.0660P)²+2.8065P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1134
_reflns_number_gt                2081
_reflns_number_total             2292
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7593sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        4390.0(9)
_cod_database_code               2241740
_cod_database_fobs_code          2241740
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.961
_shelx_estimated_absorpt_t_max   0.994
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x+1/2, z+1/4'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x, z+3/4'
'-x, y, z+1/2'
'-y, -x+1/2, z+3/4'
'x+1/2, -y+1/2, z'
'y+1/2, x, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-y+1/2, x+1, z+3/4'
'-x+1, -y+1, z+1'
'y+1, -x+1/2, z+5/4'
'-x+1/2, y+1/2, z+1'
'-y+1/2, -x+1, z+5/4'
'x+1, -y+1, z+1/2'
'y+1, x+1/2, z+3/4'
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_occupancy
S S1 0.48085(6) 0.10242(6) 0.44233(8) 0.0259(3) Uani d 1
O O1 0.36361(17) 0.16769(16) 0.56218(18) 0.0200(6) Uani d 1
O O2 0.22698(16) 0.39128(15) 0.66600(18) 0.0161(6) Uani d 1
O O3 0.25495(19) 0.40880(19) 0.8415(2) 0.0265(7) Uani d 1
O O4 0.18400(18) 0.51202(19) 0.8477(2) 0.0266(7) Uani d 1
N N1 0.31555(19) 0.25578(19) 0.4618(2) 0.0165(7) Uani d 1
H H1N 0.319(3) 0.278(2) 0.4082(17) 0.020 Uiso d 1
N N2 0.28004(19) 0.29467(19) 0.5325(2) 0.0171(7) Uani d 1
N N3 0.2125(2) 0.4568(2) 0.8067(2) 0.0196(7) Uani d 1
C C1 0.4111(2) 0.1666(2) 0.4094(3) 0.0162(8) Uani d 1
C C2 0.4137(2) 0.1857(2) 0.3137(3) 0.0206(9) Uani d 1
H H2 0.3797 0.2195 0.2824 0.025 Uiso calc 1
C C3 0.4770(2) 0.1443(2) 0.2728(3) 0.0221(9) Uani d 1
H H3 0.4901 0.1482 0.2093 0.027 Uiso calc 1
C C4 0.5164(3) 0.0990(2) 0.3336(3) 0.0251(10) Uani d 1
H H4 0.5595 0.0686 0.3166 0.030 Uiso calc 1
C C5 0.3616(2) 0.1960(2) 0.4838(3) 0.0158(8) Uani d 1
C C6 0.2361(2) 0.3499(2) 0.5074(3) 0.0170(8) Uani d 1
H H6 0.2247 0.3576 0.4439 0.020 Uiso calc 1
C C7 0.2040(2) 0.4004(2) 0.5764(3) 0.0166(8) Uani d 1
C C8 0.1580(2) 0.4633(2) 0.5673(3) 0.0183(8) Uani d 1
H H8 0.1351 0.4815 0.5120 0.022 Uiso calc 1
C C9 0.1511(2) 0.4962(2) 0.6561(3) 0.0181(8) Uani d 1
H H9 0.1228 0.5406 0.6731 0.022 Uiso calc 1
C C10 0.1940(2) 0.4502(2) 0.7116(3) 0.0160(8) Uani 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
C4 S1 C1 91.3(2)
C10 O2 C7 104.6(3)
C5 N1 N2 118.1(3)
C5 N1 H1N 120(3)
N2 N1 H1N 119(3)
C6 N2 N1 115.3(3)
O3 N3 O4 125.1(4)
O3 N3 C10 118.9(3)
O4 N3 C10 116.0(3)
C2 C1 C5 130.5(4)
C2 C1 S1 113.5(3)
C5 C1 S1 115.9(3)
C1 C2 C3 107.8(4)
C1 C2 H2 126.1
C3 C2 H2 126.1
C4 C3 C2 114.0(4)
C4 C3 H3 123.0
C2 C3 H3 123.0
C3 C4 S1 113.3(3)
C3 C4 H4 123.4
S1 C4 H4 123.4
O1 C5 N1 122.6(4)
O1 C5 C1 121.1(4)
N1 C5 C1 116.3(3)
N2 C6 C7 119.4(3)
N2 C6 H6 120.3
C7 C6 H6 120.3
O2 C7 C8 110.9(3)
O2 C7 C6 118.3(3)
C8 C7 C6 130.5(4)
C7 C8 C9 106.7(4)
C7 C8 H8 126.7
C9 C8 H8 126.7
C10 C9 C8 104.7(4)
C10 C9 H9 127.6
C8 C9 H9 127.6
O2 C10 C9 113.1(3)
O2 C10 N3 116.1(3)
C9 C10 N3 130.7(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C4 1.694(5)
S1 C1 1.718(4)
O1 C5 1.239(5)
O2 C10 1.349(5)
O2 C7 1.367(5)
O3 N3 1.225(5)
O4 N3 1.234(4)
N1 C5 1.351(5)
N1 N2 1.374(5)
N1 H1N 0.870(14)
N2 C6 1.281(5)
N3 C10 1.419(5)
C1 C2 1.427(6)
C1 C5 1.472(5)
C2 C3 1.444(6)
C2 H2 0.9500
C3 C4 1.367(6)
C3 H3 0.9500
C4 H4 0.9500
C6 C7 1.443(5)
C6 H6 0.9500
C7 C8 1.364(6)
C8 C9 1.413(6)
C8 H8 0.9500
C9 C10 1.358(6)
C9 H9 0.9500
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 H1N O1 10_544 0.87(3) 2.05(3) 2.882(4) 159(3)
C4 H4 O4 9_544 0.95 2.42 3.293(6) 152
C8 H8 O4 15_454 0.95 2.53 3.242(5) 132
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 -178.9(3)
C4 S1 C1 C2 0.7(3)
C4 S1 C1 C5 -176.2(3)
C5 C1 C2 C3 175.6(4)
S1 C1 C2 C3 -0.7(4)
C1 C2 C3 C4 0.4(5)
C2 C3 C4 S1 0.2(5)
C1 S1 C4 C3 -0.5(3)
N2 N1 C5 O1 11.6(5)
N2 N1 C5 C1 -167.3(3)
C2 C1 C5 O1 174.0(4)
S1 C1 C5 O1 -9.8(5)
C2 C1 C5 N1 -7.1(6)
S1 C1 C5 N1 169.1(3)
N1 N2 C6 C7 -172.1(3)
C10 O2 C7 C8 -0.1(4)
C10 O2 C7 C6 174.1(3)
N2 C6 C7 O2 5.4(6)
N2 C6 C7 C8 178.2(4)
O2 C7 C8 C9 -0.1(4)
C6 C7 C8 C9 -173.3(4)
C7 C8 C9 C10 0.2(4)
C7 O2 C10 C9 0.2(4)
C7 O2 C10 N3 -176.4(3)
C8 C9 C10 O2 -0.3(4)
C8 C9 C10 N3 175.8(4)
O3 N3 C10 O2 -1.7(5)
O4 N3 C10 O2 178.1(3)
O3 N3 C10 C9 -177.6(4)
O4 N3 C10 C9 2.1(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 6898871
