#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007171.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_2007171
loop_
_publ_author_name
'Ayg\"un, M.'
'I\,sik, \,S.'
'\"Ocal, N.'
'Tahir, M. N.'
'Kaban, \,S.'
'B\"uy\"ukg\"ung\"or, O.'
_publ_contact_author
;
Muhittin Aygun
Department of Physics
Faculty of Art and Science
Ondokuz Mays University
TR-55139 Kurupelit
Samsun
Turkey
;
_publ_section_title
;
 Thiophene-2-carbaldehyde
 <i>N</i>-(2,4-Dinitrophenyl)-<i>N</i>-methylhydrazone
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              527
_journal_page_last               529
_journal_volume                  54
_journal_year                    1998
_chemical_formula_sum            'C12 H10 N4 O4 S'
_chemical_formula_weight         306.30
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 93.33(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.108(2)
_cell_length_b                   10.450(2)
_cell_length_c                   15.188(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.93
_cell_measurement_theta_min      11.64
_cell_volume                     2710.7(8)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1993)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.009
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            2564
_diffrn_reflns_theta_max         26.58
_diffrn_reflns_theta_min         2.38
_diffrn_standards_decay_%        0.628
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.26
_exptl_absorpt_correction_T_max  0.949
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_type   '\y scans (North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.18
_refine_ls_extinction_coef       0.00065(11)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   0.973
_refine_ls_goodness_of_fit_obs   1.013
_refine_ls_hydrogen_treatment    'H atoms: see below'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         2462
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.973
_refine_ls_restrained_S_obs      1.013
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_obs          0.0347
_refine_ls_shift/esd_max         0.005
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0238P)^2^+2.7183P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.0771
_refine_ls_wR_factor_obs         0.0730
_reflns_number_observed          2075
_reflns_number_total             2462
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    fr1057.cif
_[local]_cod_data_source_block   nk44
_[local]_cod_cif_authors_sg_H-M  'C 2/c'
_cod_database_code               2007171
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 0.0638(3) 0.0427(3) 0.0677(3) -0.0012(2) 0.0205(3) -0.0011(2)
O1A 0.102(9) 0.069(5) 0.121(9) 0.011(6) 0.022(8) -0.031(5)
O1B 0.115(10) 0.050(3) 0.141(11) 0.000(4) 0.051(9) -0.006(4)
O2 0.0879(12) 0.0994(14) 0.1110(15) 0.0270(11) 0.0393(11) -0.0248(12)
O3 0.0818(11) 0.0595(9) 0.0418(8) -0.0091(8) 0.0124(7) -0.0032(7)
O4 0.0465(7) 0.0609(8) 0.0672(9) -0.0086(7) 0.0176(6) 0.0065(7)
N1 0.0740(14) 0.0671(13) 0.0836(15) 0.0138(11) 0.0183(12) -0.0126(12)
N2 0.0470(8) 0.0417(8) 0.0443(9) 0.0010(7) 0.0110(7) 0.0084(7)
N3 0.0472(8) 0.0438(8) 0.0502(9) -0.0076(7) 0.0113(7) 0.0045(7)
N4 0.0465(8) 0.0412(8) 0.0418(8) -0.0022(6) 0.0080(7) 0.0028(6)
C1 0.0376(9) 0.0484(10) 0.0385(9) -0.0027(8) 0.0034(7) 0.0057(8)
C2 0.0369(9) 0.0466(9) 0.0381(9) -0.0014(8) 0.0060(7) 0.0030(8)
C3 0.0443(10) 0.0468(11) 0.0482(11) -0.0006(8) 0.0047(8) 0.0036(9)
C4 0.0487(10) 0.0567(12) 0.0500(11) 0.0111(9) 0.0059(9) -0.0023(9)
C5 0.0441(11) 0.0727(14) 0.0485(12) 0.0085(10) 0.0131(9) 0.0039(10)
C6 0.0465(11) 0.0599(12) 0.0507(12) -0.0031(9) 0.0140(9) 0.0119(10)
C7 0.0601(13) 0.0521(12) 0.0559(13) -0.0178(10) 0.0072(10) 0.0039(11)
C8 0.0579(11) 0.0383(10) 0.0396(10) -0.0058(8) 0.0055(8) 0.0017(8)
C9 0.0563(10) 0.0388(9) 0.0387(10) 0.0007(8) 0.0042(8) 0.0000(8)
C10 0.0650(13) 0.0414(11) 0.0670(14) 0.0049(10) 0.0016(11) 0.0003(10)
C11 0.0576(13) 0.0598(14) 0.077(2) 0.0175(11) 0.0044(11) -0.0093(12)
C12 0.0545(12) 0.0651(14) 0.0610(13) 0.0025(11) 0.0099(10) -0.0015(11)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
S1 0.18514(3) 0.13764(5) 0.55939(4) 0.0574(2) Uani d . 1 . S
O1A -0.088(2) 0.7015(19) 0.743(2) 0.097(4) Uani d P 0.43(8) 1 O
O1B -0.114(2) 0.7087(11) 0.715(3) 0.100(6) Uani d P 0.57(8) 2 O
O2 -0.19182(11) 0.6249(2) 0.80233(13) 0.0981(6) Uani d . 1 . O
O3 -0.01764(9) 0.29261(14) 0.49004(9) 0.0607(4) Uani d . 1 . O
O4 0.06384(7) 0.41973(13) 0.55953(9) 0.0577(4) Uani d . 1 . O
N1 -0.13928(13) 0.6158(2) 0.75151(15) 0.0744(6) Uani d . 1 . N
N2 0.00476(9) 0.35404(14) 0.55485(10) 0.0440(3) Uani d . 1 . N
N3 -0.05425(9) 0.12396(14) 0.64379(10) 0.0467(4) Uani d . 1 . N
N4 0.02153(8) 0.11635(13) 0.61941(9) 0.0430(4) Uani d . 1 . N
C1 -0.07875(10) 0.2453(2) 0.66360(11) 0.0415(4) Uani d . 1 . C
C2 -0.04567(9) 0.3568(2) 0.63006(11) 0.0404(4) Uani d . 1 . C
C3 -0.06333(11) 0.4770(2) 0.65928(13) 0.0463(4) Uani d . 1 . C
C4 -0.11936(11) 0.4889(2) 0.72065(13) 0.0517(5) Uani d . 1 . C
C5 -0.15749(11) 0.3834(2) 0.75090(14) 0.0547(5) Uani d . 1 . C
C6 -0.13727(11) 0.2644(2) 0.72365(13) 0.0519(5) Uani d . 1 . C
C7 -0.10158(14) 0.0106(2) 0.6570(2) 0.0559(5) Uani d . 1 . C
C8 0.05237(11) 0.0074(2) 0.60498(12) 0.0451(4) Uani d . 1 . C
C9 0.13191(11) 0.0017(2) 0.57881(12) 0.0445(4) Uani d . 1 . C
C10 0.17475(13) -0.1051(2) 0.5627(2) 0.0579(5) Uani d . 1 . C
C11 0.24959(13) -0.0762(2) 0.5345(2) 0.0646(6) Uani d . 1 . C
C12 0.26335(13) 0.0491(2) 0.52966(15) 0.0599(5) Uani d . 1 . C
H3 -0.0418(10) 0.5456(18) 0.6373(12) 0.047(5) Uiso d . 1 . H
H5 -0.1967(12) 0.394(2) 0.7931(14) 0.069(6) Uiso d . 1 . H
H6 -0.1595(11) 0.197(2) 0.7456(13) 0.056(6) Uiso d . 1 . H
H7A -0.0982(12) -0.050(2) 0.6083(15) 0.072(7) Uiso d . 1 . H
H7B -0.0799(13) -0.038(2) 0.7091(16) 0.082(8) Uiso d . 1 . H
H7C -0.1556(14) 0.037(2) 0.6575(15) 0.078(7) Uiso d . 1 . H
H8 0.0260(10) -0.0695(18) 0.6100(11) 0.045(5) Uiso d . 1 . H
H10 0.1548(12) -0.182(2) 0.5711(14) 0.061(6) Uiso d . 1 . H
H11 0.2850(13) -0.138(2) 0.5226(15) 0.077(7) Uiso d . 1 . H
H12 0.3093(13) 0.093(2) 0.5157(14) 0.070(7) Uiso d . 1 . H
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
_geom_angle_publ_flag
C12 S1 C9 91.63(11) yes
O1B N1 O2 121.2(7) yes
O2 N1 O1A 123.6(8) yes
O1B N1 C4 119.4(6) ?
O2 N1 C4 118.0(2) ?
O1A N1 C4 115.5(11) ?
O3 N2 O4 124.3(2) yes
O3 N2 C2 117.82(15) ?
O4 N2 C2 117.7(2) ?
N4 N3 C1 114.69(14) yes
N4 N3 C7 122.2(2) yes
C1 N3 C7 122.8(2) ?
C8 N4 N3 120.24(15) yes
N3 C1 C2 123.5(2) ?
N3 C1 C6 120.7(2) ?
C2 C1 C6 115.7(2) ?
C3 C2 C1 122.8(2) ?
C3 C2 N2 114.8(2) ?
C1 C2 N2 122.1(2) ?
C2 C3 C4 118.4(2) ?
C2 C3 H3 121.2(12) ?
C4 C3 H3 120.3(12) ?
C5 C4 C3 121.0(2) ?
C5 C4 N1 120.0(2) ?
C3 C4 N1 119.0(2) ?
C6 C5 C4 119.8(2) ?
C6 C5 H5 120.2(13) ?
C4 C5 H5 119.9(13) ?
C5 C6 C1 122.0(2) ?
C5 C6 H6 119.7(13) ?
C1 C6 H6 118.3(13) ?
N3 C7 H7A 111.3(13) ?
N3 C7 H7B 109.9(14) ?
H7A C7 H7B 103.7(19) ?
N3 C7 H7C 108.2(14) ?
H7A C7 H7C 106.8(19) ?
H7B C7 H7C 116.9(19) ?
N4 C8 C9 119.3(2) yes
N4 C8 H8 123.4(11) ?
C9 C8 H8 117.3(11) ?
C10 C9 C8 127.5(2) ?
C10 C9 S1 110.4(2) yes
C8 C9 S1 122.02(14) ?
C9 C10 C11 112.8(2) ?
C9 C10 H10 120.0(14) ?
C11 C10 H10 127.2(13) ?
C12 C11 C10 113.2(2) ?
C12 C11 H11 124.2(15) ?
C10 C11 H11 122.6(15) ?
C11 C12 S1 111.9(2) yes
C11 C12 H12 130.1(13) ?
S1 C12 H12 117.9(13) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C12 1.709(2) yes
S1 C9 1.722(2) yes
O1A N1 1.27(2) yes
O1B N1 1.207(13) yes
O2 N1 1.222(2) yes
O3 N2 1.218(2) yes
O4 N2 1.220(2) yes
N1 C4 1.453(3) yes
N2 C2 1.471(2) yes
N3 N4 1.371(2) yes
N3 C1 1.375(2) yes
N3 C7 1.455(2) yes
N4 C8 1.279(2) yes
C1 C2 1.404(2) ?
C1 C6 1.407(3) ?
C2 C3 1.372(3) ?
C3 C4 1.381(3) ?
C3 H3 0.88(2) ?
C4 C5 1.374(3) ?
C5 C6 1.361(3) ?
C5 H5 0.96(2) ?
C6 H6 0.88(2) ?
C7 H7A 0.98(2) ?
C7 H7B 0.99(2) ?
C7 H7C 0.96(2) ?
C8 C9 1.441(3) yes
C8 H8 0.93(2) ?
C9 C10 1.364(3) yes
C10 C11 1.406(3) yes
C10 H10 0.88(2) ?
C11 C12 1.334(3) yes
C11 H11 0.91(2) ?
C12 H12 0.95(2) ?
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
_geom_torsion_publ_flag
C1 N3 N4 C8 175.5(2) yes
C7 N3 N4 C8 2.0(3) ?
N4 N3 C1 C2 24.8(2) yes
C7 N3 C1 C2 -161.8(2) ?
N4 N3 C1 C6 -152.0(2) ?
C7 N3 C1 C6 21.5(3) ?
N3 C1 C2 C3 -171.1(2) ?
C6 C1 C2 C3 5.8(3) ?
N3 C1 C2 N2 15.0(3) ?
C6 C1 C2 N2 -168.1(2) ?
O3 N2 C2 C3 -127.0(2) ?
O4 N2 C2 C3 48.6(2) ?
O3 N2 C2 C1 47.4(2) ?
O4 N2 C2 C1 -137.0(2) ?
C1 C2 C3 C4 -3.8(3) ?
N2 C2 C3 C4 170.6(2) ?
C2 C3 C4 C5 -1.0(3) ?
C2 C3 C4 N1 -179.3(2) yes
O1B N1 C4 C5 -169.(3) ?
O2 N1 C4 C5 -2.1(3) ?
O1A N1 C4 C5 160.(2) ?
O1B N1 C4 C3 9.(3) ?
O2 N1 C4 C3 176.3(2) ?
O1A N1 C4 C3 -22.(2) ?
C3 C4 C5 C6 3.4(3) ?
N1 C4 C5 C6 -178.3(2) ?
C4 C5 C6 C1 -1.1(3) ?
N3 C1 C6 C5 173.7(2) ?
C2 C1 C6 C5 -3.3(3) ?
N3 N4 C8 C9 179.6(2) yes
N4 C8 C9 C10 178.4(2) ?
N4 C8 C9 S1 -4.2(3) yes
C12 S1 C9 C10 0.3(2) ?
C12 S1 C9 C8 -177.5(2) ?
C8 C9 C10 C11 177.3(2) ?
S1 C9 C10 C11 -0.3(2) ?
C9 C10 C11 C12 0.2(3) ?
C10 C11 C12 S1 0.0(3) yes
C9 S1 C12 C11 -0.2(2) ?