#------------------------------------------------------------------------------
#$Date: 2017-01-06 10:05:08 +0200 (Fri, 06 Jan 2017) $
#$Revision: 189974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/06/2020651.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_2020651
loop_
_publ_author_name
'Cardoso, Laura N. F.'
'Noguiera, Thais C. M.'
'Kaiser, Carlos R.'
'Wardell, James L.'
'de Souza, Marcus V. N.'
'Lancaster, Shaun T.'
'Harrison, William T. A.'
_publ_section_title
;
 Different weak interactions in the crystals of three isomeric
 (E)-N-methyl-N'-(nitrobenzylidene)-2-(thiophen-2-yl)acetohydrazides
;
_journal_coeditor_code           HG5478
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1677
_journal_page_last               1682
_journal_paper_doi               10.1107/S2056989016016856
_journal_volume                  72
_journal_year                    2016
_chemical_formula_moiety         'C14 H13 N3 O3 S'
_chemical_formula_sum            'C14 H13 N3 O3 S'
_chemical_formula_weight         303.33
_chemical_name_systematic
(E)-N-Methyl-N'-(3-nitrobenzylidene)-2-(thiophen-2-yl)acetohydrazide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 93.3800(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6629(4)
_cell_length_b                   15.6864(11)
_cell_length_c                   15.2842(11)
_cell_measurement_reflns_used    9051
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     1355.34(17)
_computing_cell_refinement
;
CrystalClear (Rigaku, 2012)
;
_computing_data_collection
;
CrystalClear (Rigaku, 2012)
;
_computing_data_reduction
;
CrystalClear (Rigaku, 2012)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9365
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.597
_exptl_absorpt_coefficient_mu    0.253
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.279
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0335
_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)+(0.0505P)²+0.4026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0955
_reflns_number_gt                2757
_reflns_number_total             3110
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hg5478sup1.cif
_cod_data_source_block           II
_cod_depositor_comments
'Adding full bibliography for 2020650--2020652.cif.'
_cod_database_code               2020651
_cod_database_fobs_code          2020651
_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.
;
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'
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
C C1 0.3945(2) 0.25348(8) 0.28563(8) 0.0187(2) Uani d 1
C C2 0.4786(2) 0.33560(8) 0.27161(8) 0.0188(2) Uani d 1
H H2 0.6256 0.3540 0.2983 0.023 Uiso calc 1
C C3 0.3425(2) 0.38950(8) 0.21792(8) 0.0192(3) Uani d 1
C C4 0.1240(2) 0.36637(9) 0.17844(8) 0.0212(3) Uani d 1
H H4 0.0333 0.4055 0.1430 0.025 Uiso calc 1
C C5 0.0432(2) 0.28453(9) 0.19246(8) 0.0225(3) Uani d 1
H H5 -0.1045 0.2667 0.1659 0.027 Uiso calc 1
C C6 0.1768(2) 0.22833(8) 0.24516(8) 0.0210(3) Uani d 1
H H6 0.1202 0.1721 0.2539 0.025 Uiso calc 1
C C7 0.5216(2) 0.19343(8) 0.34489(8) 0.0198(3) Uani d 1
H H7 0.4668 0.1365 0.3494 0.024 Uiso calc 1
C C8 0.7162(2) 0.07490(8) 0.45928(9) 0.0225(3) Uani d 1
H H8A 0.5539 0.0795 0.4777 0.034 Uiso calc 1
H H8B 0.8134 0.0441 0.5040 0.034 Uiso calc 1
H H8C 0.7160 0.0439 0.4036 0.034 Uiso calc 1
C C9 1.0134(2) 0.18638(9) 0.49611(8) 0.0199(3) Uani d 1
C C10 1.1004(2) 0.27656(8) 0.48044(8) 0.0211(3) Uani d 1
H H10A 1.2731 0.2785 0.4947 0.025 Uiso calc 1
H H10B 1.0732 0.2901 0.4174 0.025 Uiso calc 1
C C11 0.9841(2) 0.34407(8) 0.53279(8) 0.0195(3) Uani d 1
C C12 1.0854(2) 0.38920(9) 0.60202(9) 0.0239(3) Uani d 1
H H12 1.2409 0.3788 0.6265 0.029 Uiso calc 1
C C13 0.9330(2) 0.45351(9) 0.63371(9) 0.0248(3) Uani d 1
H H13 0.9760 0.4907 0.6810 0.030 Uiso calc 1
C C14 0.7188(2) 0.45511(9) 0.58811(9) 0.0253(3) Uani d 1
H H14 0.5950 0.4936 0.5998 0.030 Uiso calc 1
N N1 0.70671(18) 0.21766(7) 0.39066(7) 0.0189(2) Uani d 1
N N2 0.81324(18) 0.15999(7) 0.44806(7) 0.0195(2) Uani d 1
N N3 0.43337(19) 0.47517(7) 0.20197(7) 0.0213(2) Uani d 1
O O1 1.11711(16) 0.13877(6) 0.54872(6) 0.0251(2) Uani d 1
O O2 0.31572(17) 0.52296(6) 0.15251(6) 0.0262(2) Uani d 1
O O3 0.62386(17) 0.49615(7) 0.23846(7) 0.0291(2) Uani d 1
S S1 0.69978(5) 0.37937(2) 0.50723(2) 0.02407(11) 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
C2 C1 C6 119.43(11)
C2 C1 C7 121.93(11)
C6 C1 C7 118.58(12)
C3 C2 C1 118.24(11)
C3 C2 H2 120.9
C1 C2 H2 120.9
C2 C3 C4 123.26(12)
C2 C3 N3 118.13(11)
C4 C3 N3 118.62(11)
C5 C4 C3 117.93(12)
C5 C4 H4 121.0
C3 C4 H4 121.0
C4 C5 C6 120.32(11)
C4 C5 H5 119.8
C6 C5 H5 119.8
C5 C6 C1 120.80(12)
C5 C6 H6 119.6
C1 C6 H6 119.6
N1 C7 C1 120.14(12)
N1 C7 H7 119.9
C1 C7 H7 119.9
N2 C8 H8A 109.5
N2 C8 H8B 109.5
H8A C8 H8B 109.5
N2 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O1 C9 N2 121.03(12)
O1 C9 C10 121.63(11)
N2 C9 C10 117.35(11)
C11 C10 C9 114.54(11)
C11 C10 H10A 108.6
C9 C10 H10A 108.6
C11 C10 H10B 108.6
C9 C10 H10B 108.6
H10A C10 H10B 107.6
C12 C11 C10 126.76(11)
C12 C11 S1 110.59(10)
C10 C11 S1 122.55(9)
C11 C12 C13 113.09(12)
C11 C12 H12 123.5
C13 C12 H12 123.5
C14 C13 C12 112.11(12)
C14 C13 H13 123.9
C12 C13 H13 123.9
C13 C14 S1 111.86(11)
C13 C14 H14 124.1
S1 C14 H14 124.1
C7 N1 N2 117.82(11)
N1 N2 C9 117.31(11)
N1 N2 C8 121.56(10)
C9 N2 C8 121.11(10)
O3 N3 O2 122.93(11)
O3 N3 C3 118.52(10)
O2 N3 C3 118.55(10)
C14 S1 C11 92.35(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3943(18)
C1 C6 1.4027(16)
C1 C7 1.4659(17)
C2 C3 1.3811(17)
C2 H2 0.9500
C3 C4 1.3923(17)
C3 N3 1.4645(17)
C4 C5 1.3839(19)
C4 H4 0.9500
C5 C6 1.3883(18)
C5 H5 0.9500
C6 H6 0.9500
C7 N1 1.2829(16)
C7 H7 0.9500
C8 N2 1.4573(16)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 O1 1.2220(16)
C9 N2 1.3776(15)
C9 C10 1.5215(18)
C10 C11 1.5025(18)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C12 1.3705(18)
C11 S1 1.7256(12)
C12 C13 1.4306(19)
C12 H12 0.9500
C13 C14 1.3630(18)
C13 H13 0.9500
C14 S1 1.7134(14)
C14 H14 0.9500
N1 N2 1.3747(14)
N3 O3 1.2297(14)
N3 O2 1.2321(14)
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
C7 H7 O2 2_545 0.95 2.39 3.2879(16) 157
C8 H8B O2 4_666 0.98 2.50 3.3468(16) 144
C8 H8C O3 2_645 0.98 2.52 3.4356(17) 156
C13 H13 O3 3_766 0.95 2.52 3.1874(16) 127
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
C6 C1 C2 C3 0.08(18)
C7 C1 C2 C3 -177.02(12)
C1 C2 C3 C4 1.15(19)
C1 C2 C3 N3 -178.86(11)
C2 C3 C4 C5 -1.5(2)
N3 C3 C4 C5 178.49(12)
C3 C4 C5 C6 0.64(19)
C4 C5 C6 C1 0.5(2)
C2 C1 C6 C5 -0.90(19)
C7 C1 C6 C5 176.30(12)
C2 C1 C7 N1 5.17(19)
C6 C1 C7 N1 -171.96(12)
O1 C9 C10 C11 -95.28(14)
N2 C9 C10 C11 85.18(14)
C9 C10 C11 C12 108.80(15)
C9 C10 C11 S1 -75.20(14)
C10 C11 C12 C13 175.57(13)
S1 C11 C12 C13 -0.83(15)
C11 C12 C13 C14 0.49(18)
C12 C13 C14 S1 0.08(16)
C1 C7 N1 N2 177.17(11)
C7 N1 N2 C9 179.26(11)
C7 N1 N2 C8 -2.03(17)
O1 C9 N2 N1 179.67(11)
C10 C9 N2 N1 -0.78(16)
O1 C9 N2 C8 0.95(19)
C10 C9 N2 C8 -179.50(11)
C2 C3 N3 O3 -1.60(18)
C4 C3 N3 O3 178.39(12)
C2 C3 N3 O2 178.30(11)
C4 C3 N3 O2 -1.70(17)
C13 C14 S1 C11 -0.47(12)
C12 C11 S1 C14 0.74(11)
C10 C11 S1 C14 -175.84(11)
