##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_journal_date_recd_electronic     2020-02-17
_journal_date_accepted     2020-03-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2020
_journal_volume     76
_journal_issue      4
_journal_page_first     557
_journal_page_last     561
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989020003011
_journal_coeditor_code     RZ5271
_publ_contact_author_name     'Valeri V. Mossine'
_publ_contact_author_address
;
Department of Biochemistry
University of Missouri
Columbia, MO 65211
U.S.A.
;
_publ_contact_author_email     'mossinev@missouri.edu'
_publ_contact_author_fax     '1-573-884-4631'
_publ_contact_author_phone     '1-573-882-2608'
_publ_section_title
;
Intramolecular 1,5-S...N σ-hole interaction in
(E)-N'-(pyridin-4-ylmethylidene)thiophene-2-carbohydrazide
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Mossine, Valeri V.' .
;
Department of Biochemistry
University of Missouri
Columbia, MO 65211
USA
;
    'Kelley, Steven P.' .
;
Department of Chemistry
University of Missouri
Columbia, MO 65211
USA
;
    'Mawhinney, Thomas P.' .
;
Department of Biochemistry
University of Missouri
Columbia, MO 65211
USA
;
_publ_section_synopsis
;
The hydrazide-hydrazone forms inverse dimers via hydrogen bonding, but
its conformation is defined by the presence of an intramolecular chalcogen
bond. Electrostatic forces dominate in the crystal packing and give rise to a
layered supramolecular structure.
;
_chemical_name_systematic
;
(E)-N'-(Pyridin-4-ylmethylidene)thiophene-2-carbohydrazide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C11 H9 N3 O S'
_chemical_formula_sum     'C11 H9 N3 O S'
_chemical_formula_iupac     'C11 H9 N3 O S'
_chemical_formula_weight     231.27
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 1 21/n 1'
_space_group_name_Hall     '-P 2yn'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     12.0600(8)
_cell_length_b     4.4531(3)
_cell_length_c     19.9528(13)
_cell_angle_alpha     90
_cell_angle_beta     102.228(2)
_cell_angle_gamma     90
_cell_volume     1047.24(12)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     8101
_cell_measurement_theta_min     2.20
_cell_measurement_theta_max     32.30
_cell_measurement_temperature     100.0
_exptl_crystal_description     needle
_exptl_crystal_colour     'clear colourless'
_exptl_crystal_size_max     0.49
_exptl_crystal_size_mid     0.04
_exptl_crystal_size_min     0.01
_exptl_crystal_density_diffrn     1.467
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     480
_exptl_absorpt_coefficient_mu     0.289
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(AXScale; Bruker, 2016)
;
_exptl_absorpt_correction_T_min     0.6939
_exptl_absorpt_correction_T_max     0.7464
_diffrn_ambient_temperature     100.0
_diffrn_source     'Sealed Source Mo with TRIUMPH optics'
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'omega and phi scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     25531
_diffrn_reflns_av_R_equivalents     0.0591
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_theta_min     2.200
_diffrn_reflns_theta_max     32.425
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -18
_diffrn_reflns_limit_h_max     18
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -30
_diffrn_reflns_limit_l_max     30
_diffrn_standards_number     0
_refine_special_details     ?
_reflns_number_total     3767
_reflns_number_gt     2821
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0646
_refine_ls_R_factor_gt     0.0397
_refine_ls_wR_factor_gt     0.0917
_refine_ls_wR_factor_ref     0.1013
_refine_ls_goodness_of_fit_ref     1.031
_refine_ls_restrained_S_all     1.031
_refine_ls_number_reflns     3767
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refxyz
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0482P)²+0.4155P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.436
_refine_diff_density_min     -0.285
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
_computing_data_collection
;
SAINT (Bruker, 2016)
;
_computing_cell_refinement
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2008)
;
_computing_structure_refinement
;
ShelXL (Sheldrick, 2015)
;
_computing_molecular_graphics
;
OLEX2(Dolomanov et al.,  2009),
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.86385(3) 0.41227(8) 0.09663(2) 0.01759(9) Uani d 1 . .
    O O1 0.57985(7) -0.0566(2) 0.08737(5) 0.01585(19) Uani d 1 . .
    N N1 0.67837(8) 0.4814(2) -0.01319(5) 0.0121(2) Uani d 1 . .
    C C3 0.86828(11) 1.1139(3) -0.10148(7) 0.0177(3) Uani d 1 . .
    C C6 0.63662(10) 0.6002(3) -0.07173(6) 0.0123(2) Uani d 1 . .
    N N2 0.61184(9) 0.2710(2) 0.00868(5) 0.0125(2) Uani d 1 . .
    C C8 0.75495(10) 0.1986(3) 0.11541(6) 0.0128(2) Uani d 1 . .
    C C7 0.64471(10) 0.1304(3) 0.06997(6) 0.0119(2) Uani d 1 . .
    N N3 0.82339(9) 1.2476(3) -0.16131(6) 0.0170(2) Uani d 1 . .
    C C1 0.70133(10) 0.8252(3) -0.10079(6) 0.0117(2) Uani d 1 . .
    C C10 0.89639(12) 0.1627(4) 0.21440(7) 0.0214(3) Uani d 1 . .
    C C2 0.81256(10) 0.9054(3) -0.06925(7) 0.0158(2) Uani d 1 . .
    C C9 0.78539(11) 0.0796(3) 0.18034(7) 0.0191(3) Uani d 1 . .
    C C5 0.65308(11) 0.9644(3) -0.16254(6) 0.0146(2) Uani d 1 . .
    C C4 0.71673(11) 1.1716(3) -0.19047(7) 0.0162(2) Uani d 1 . .
    C C11 0.94837(11) 0.3405(3) 0.17495(7) 0.0190(3) Uani d 1 . .
    H H2 0.5467(15) 0.214(4) -0.0197(9) 0.023 Uiso d 1 . .
    H H6 0.5592(15) 0.543(4) -0.0981(9) 0.023 Uiso d 1 . .
    H H5 0.5756(15) 0.918(4) -0.1848(9) 0.023 Uiso d 1 . .
    H H2A 0.8487(14) 0.813(4) -0.0278(9) 0.023 Uiso d 1 . .
    H H4 0.6850(14) 1.273(4) -0.2329(9) 0.023 Uiso d 1 . .
    H H9 0.7381(14) -0.038(4) 0.1991(9) 0.023 Uiso d 1 . .
    H H3 0.9464(15) 1.168(4) -0.0810(9) 0.023 Uiso d 1 . .
    H H11 1.0212(15) 0.424(4) 0.1851(9) 0.023 Uiso d 1 . .
    H H10 0.9262(15) 0.103(4) 0.2563(9) 0.023 Uiso d 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    S1 C11 . 1.7055(14) ?
    S1 C8 . 1.7259(12) ?
    O1 C7 . 1.2410(15) ?
    N1 C6 . 1.2839(16) ?
    N1 N2 . 1.3643(14) ?
    C3 N3 . 1.3413(18) ?
    C3 C2 . 1.3821(18) ?
    C3 H3 . 0.974(17) ?
    C6 C1 . 1.4631(17) ?
    C6 H6 . 1.002(17) ?
    N2 C7 . 1.3561(15) ?
    N2 H2 . 0.901(18) ?
    C8 C9 . 1.3756(18) ?
    C8 C7 . 1.4736(16) ?
    N3 C4 . 1.3381(17) ?
    C1 C5 . 1.3918(17) ?
    C1 C2 . 1.4019(17) ?
    C10 C11 . 1.360(2) ?
    C10 C9 . 1.4161(19) ?
    C10 H10 . 0.879(17) ?
    C2 H2A . 0.944(17) ?
    C9 H9 . 0.912(18) ?
    C5 C4 . 1.3900(18) ?
    C5 H5 . 0.968(17) ?
    C4 H4 . 0.963(17) ?
    C11 H11 . 0.936(18) ?
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
    C11 S1 C8 . . 91.85(6) ?
    C6 N1 N2 . . 115.48(10) ?
    N3 C3 C2 . . 124.61(12) ?
    N3 C3 H3 . . 115.8(10) ?
    C2 C3 H3 . . 119.5(10) ?
    N1 C6 C1 . . 120.21(11) ?
    N1 C6 H6 . . 121.1(10) ?
    C1 C6 H6 . . 118.7(10) ?
    C7 N2 N1 . . 121.75(10) ?
    C7 N2 H2 . . 119.0(11) ?
    N1 N2 H2 . . 119.0(11) ?
    C9 C8 C7 . . 121.75(11) ?
    C9 C8 S1 . . 110.68(9) ?
    C7 C8 S1 . . 127.51(9) ?
    O1 C7 N2 . . 118.73(11) ?
    O1 C7 C8 . . 120.41(11) ?
    N2 C7 C8 . . 120.86(11) ?
    C4 N3 C3 . . 116.38(11) ?
    C5 C1 C2 . . 117.70(11) ?
    C5 C1 C6 . . 119.85(11) ?
    C2 C1 C6 . . 122.44(11) ?
    C11 C10 C9 . . 112.28(12) ?
    C11 C10 H10 . . 125.6(12) ?
    C9 C10 H10 . . 122.2(12) ?
    C3 C2 C1 . . 118.39(12) ?
    C3 C2 H2A . . 121.5(10) ?
    C1 C2 H2A . . 120.1(10) ?
    C8 C9 C10 . . 112.84(12) ?
    C8 C9 H9 . . 122.8(11) ?
    C10 C9 H9 . . 124.3(11) ?
    C4 C5 C1 . . 119.19(12) ?
    C4 C5 H5 . . 121.3(10) ?
    C1 C5 H5 . . 119.5(10) ?
    N3 C4 C5 . . 123.72(12) ?
    N3 C4 H4 . . 115.5(10) ?
    C5 C4 H4 . . 120.8(10) ?
    C10 C11 S1 . . 112.35(10) ?
    C10 C11 H11 . . 129.3(11) ?
    S1 C11 H11 . . 118.3(11) ?
_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     0.872
_shelx_estimated_absorpt_T_max     0.997
