#------------------------------------------------------------------------------
#$Date: 2011-09-10 05:16:28 +0200 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006167.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_2006167
loop_
_publ_author_name
'Wong, M. S.'
'Gramlich, V.'
'Pan, F.'
'Bosshard, C.'
'G\"unter, P.'
_publ_section_title
;
 5-Methylthiophene-2-carboxaldehyde 4-Nitrophenylhydrazone--Water (1/1)
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              757
_journal_page_last               759
_journal_volume                  53
_journal_year                    1997
_chemical_formula_iupac          'C12 H11 N3 O2 S, H2 O1'
_chemical_formula_sum            'C12 H13 N3 O3 S'
_chemical_formula_weight         279.31
_chemical_name_common            MTNPH
_chemical_name_systematic
;
5-methylthiophenecarboxaldehyde-4-nitrophenylhydrazone monohydrate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_creation_method           SHELXL93
_cell_angle_alpha                90.00
_cell_angle_beta                 93.17(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.844(7)
_cell_length_b                   3.901(3)
_cell_length_c                   17.245(15)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      10
_cell_volume                     661.2(9)
_computing_cell_refinement       'P3 Users Manual'
_computing_data_collection       'P3 Users Manual (Siemens, 1992)'
_computing_data_reduction        'SHELXTL-Plus (Sheldrick, 1990)'
_computing_molecular_graphics    SHELXTL-Plus
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    SHELXTL-Plus
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Syntex P2~1~ four-circle'
_diffrn_measurement_method       \w
_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  0.0785
_diffrn_reflns_av_sigmaI/netI    0.1106
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            3454
_diffrn_reflns_theta_max         32
_diffrn_reflns_theta_min         2.07
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured '
_exptl_crystal_description       prism
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.251
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.03(11)
_refine_ls_extinction_coef       0.005(2)
_refine_ls_extinction_method     SHELXL93
_refine_ls_goodness_of_fit_all   0.674
_refine_ls_goodness_of_fit_obs   0.996
_refine_ls_hydrogen_treatment    'H atoms: see below'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2594
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.674
_refine_ls_restrained_S_obs      0.996
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_obs          0.0385
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^) + (0.0318P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.0815
_refine_ls_wR_factor_obs         0.0748
_reflns_number_observed          1112
_reflns_number_total             2594
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    ab1423.cif
_[local]_cod_data_source_block   dan1
_[local]_cod_cif_authors_sg_H-M  'P 21'
_cod_database_code               2006167
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
S 0.0469(4) 0.0454(4) 0.0495(4) -0.0038(5) 0.0062(3) 0.0012(5)
N1 0.058(2) 0.072(3) 0.062(2) 0.002(2) 0.0063(14) -0.026(2)
N2 0.0534(14) 0.052(2) 0.0425(13) -0.0024(14) 0.0025(11) 0.0003(13)
N3 0.054(2) 0.067(2) 0.0405(14) -0.013(2) 0.0043(13) 0.0083(15)
O1 0.0611(15) 0.119(3) 0.094(2) -0.023(2) 0.0198(14) 0.000(2)
O2 0.0635(14) 0.147(3) 0.0683(14) -0.004(3) -0.0102(11) -0.020(2)
C1 0.046(2) 0.035(2) 0.052(2) -0.002(2) 0.0066(13) -0.002(2)
C2 0.050(2) 0.051(2) 0.063(2) -0.003(2) 0.014(2) 0.001(2)
C3 0.044(2) 0.060(2) 0.064(2) -0.002(2) -0.003(2) -0.006(2)
C4 0.053(2) 0.039(2) 0.052(2) 0.007(2) 0.0005(13) -0.004(2)
C5 0.080(2) 0.056(3) 0.054(2) 0.001(2) -0.006(2) -0.002(2)
C6 0.058(2) 0.045(2) 0.051(2) 0.000(2) 0.013(2) 0.000(2)
C7 0.051(2) 0.043(2) 0.0391(15) 0.002(2) 0.0049(13) -0.0027(14)
C8 0.059(2) 0.054(2) 0.040(2) -0.003(2) 0.0105(15) 0.005(2)
C9 0.058(2) 0.059(2) 0.041(2) 0.006(2) 0.0003(14) -0.003(2)
C10 0.049(2) 0.047(2) 0.0480(15) -0.006(2) 0.0080(12) -0.016(2)
C11 0.057(2) 0.052(3) 0.046(2) -0.011(2) 0.0113(13) 0.001(2)
C12 0.061(2) 0.050(2) 0.0402(14) -0.005(2) 0.0066(12) 0.000(2)
O1W 0.068(2) 0.100(3) 0.083(2) -0.014(2) 0.009(2) 0.003(2)
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_type_symbol
S 0.40396(7) 0.2768 0.07180(4) 0.0471(2) Uani d . 1 S
N1 1.1457(3) 0.3460(9) 0.3692(2) 0.0637(10) Uani d . 1 N
N2 0.5354(2) 0.1264(8) 0.23212(13) 0.0492(6) Uani d . 1 N
N3 0.5998(3) 0.0453(8) 0.30243(14) 0.0538(7) Uani d . 1 N
H3N 0.557(3) -0.062(8) 0.3369(13) 0.041(8) Uiso d . 1 H
O1 1.2075(2) 0.5160(9) 0.32268(14) 0.0905(10) Uani d . 1 O
O2 1.1992(2) 0.2465(12) 0.43152(12) 0.0934(10) Uani d . 1 O
C1 0.3325(3) 0.0991(8) 0.1518(2) 0.0443(7) Uani d . 1 C
C2 0.2002(3) 0.0232(10) 0.1353(2) 0.0540(8) Uani d . 1 C
H2 0.1435(3) -0.0705(10) 0.1711(2) 0.065 Uiso calc R 1 H
C3 0.1574(3) 0.1016(10) 0.0577(2) 0.0561(9) Uani d . 1 C
H3A 0.0694(3) 0.0597(10) 0.0375(2) 0.067 Uiso calc R 1 H
C4 0.2526(3) 0.2395(11) 0.0159(2) 0.0479(8) Uani d . 1 C
C5 0.2452(3) 0.3520(10) -0.0670(2) 0.0640(11) Uani d . 1 C
H5A 0.3175(15) 0.247(5) -0.0935(3) 0.096 Uiso calc R 1 H
H5B 0.254(2) 0.5968(11) -0.0693(2) 0.096 Uiso calc R 1 H
H5C 0.1592(10) 0.285(5) -0.0913(4) 0.096 Uiso calc R 1 H
C6 0.4110(3) 0.0388(9) 0.2232(2) 0.0511(8) Uani d . 1 C
H6 0.367(2) -0.068(7) 0.2660(13) 0.047(8) Uiso d . 1 H
C7 0.7329(3) 0.1219(8) 0.31731(15) 0.0444(7) Uani d . 1 C
C8 0.7959(3) 0.0273(10) 0.3891(2) 0.0504(8) Uani d . 1 C
H8 0.742(3) -0.071(8) 0.4288(14) 0.056(9) Uiso d . 1 H
C9 0.9305(3) 0.0979(9) 0.4052(2) 0.0530(8) Uani d . 1 C
H9 0.9721(3) 0.0341(9) 0.4527(2) 0.064 Uiso calc R 1 H
C10 1.0049(3) 0.2635(12) 0.35095(15) 0.0478(7) Uani d . 1 C
C11 0.9445(3) 0.3574(8) 0.2799(2) 0.0511(9) Uani d . 1 C
H11 0.9961(3) 0.4664(8) 0.2436(2) 0.061 Uiso calc R 1 H
C12 0.8107(3) 0.2923(12) 0.26235(14) 0.0500(7) Uani d . 1 C
H12 0.7705(3) 0.3592(12) 0.21466(14) 0.060 Uiso calc R 1 H
O1W 0.4667(3) -0.2938(11) 0.4377(2) 0.0835(11) Uani d . 1 O
H1W 0.391(4) -0.366(13) 0.424(2) 0.12(2) Uiso d . 1 H
H2W 0.461(4) -0.111(11) 0.467(2) 0.09(2) 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
C1 S C4 92.0(2) yes
O1 N1 O2 122.4(3) yes
O1 N1 C10 119.0(3) yes
O2 N1 C10 118.6(3) yes
C6 N2 N3 116.1(3) yes
C7 N3 N2 120.7(3) yes
C7 N3 H3N 118.9(17) ?
N2 N3 H3N 120.3(17) ?
C2 C1 C6 127.7(3) ?
C2 C1 S 110.5(2) ?
C6 C1 S 121.8(2) ?
C1 C2 C3 112.7(3) ?
C1 C2 H2 123.7 ?
C3 C2 H2 123.7 ?
C4 C3 C2 114.7(3) ?
C4 C3 H3A 122.6 ?
C2 C3 H3A 122.6 ?
C3 C4 C5 129.8(3) ?
C3 C4 S 110.1(2) ?
C5 C4 S 120.1(2) ?
C4 C5 H5A 109.5 ?
C4 C5 H5B 109.5 ?
H5A C5 H5B 109.5 ?
C4 C5 H5C 109.5 ?
H5A C5 H5C 109.5 ?
H5B C5 H5C 109.5 ?
N2 C6 C1 121.9(3) ?
N2 C6 H6 119.5 ?
C1 C6 H6 118.6 ?
N3 C7 C8 119.0(3) ?
N3 C7 C12 122.0(3) ?
C8 C7 C12 119.0(3) ?
C9 C8 C7 120.1(3) ?
C9 C8 H8 119.9 ?
C7 C8 H8 119.8 ?
C8 C9 C10 120.2(3) ?
C8 C9 H9 119.9 ?
C10 C9 H9 119.9 ?
C9 C10 C11 120.5(3) ?
C9 C10 N1 119.8(3) ?
C11 C10 N1 119.7(3) ?
C12 C11 C10 120.8(3) ?
C12 C11 H11 119.6 ?
C10 C11 H11 119.6 ?
C11 C12 C7 119.5(3) ?
C11 C12 H12 120.3 ?
C7 C12 H12 120.3 ?
H1W O1W H2W 111(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S C1 1.728(3) yes
S C4 1.735(3) yes
N1 O1 1.227(3) yes
N1 O2 1.234(3) yes
N1 C10 1.441(4) yes
N2 C6 1.272(4) yes
N2 N3 1.374(3) yes
N3 C7 1.354(4) yes
N3 H3N 0.86(2) ?
C1 C2 1.350(4) ?
C1 C6 1.435(4) ?
C2 C3 1.415(4) ?
C2 H2 0.93 ?
C3 C4 1.328(4) ?
C3 H3A 0.93 ?
C4 C5 1.493(4) ?
C5 H5A 0.96 ?
C5 H5B 0.96 ?
C5 H5C 0.96 ?
C6 H6 0.97(2) ?
C7 C8 1.404(4) ?
C7 C12 1.417(4) ?
C8 C9 1.366(4) ?
C8 H8 0.97(3) ?
C9 C10 1.380(4) ?
C9 H9 0.93 ?
C10 C11 1.382(4) ?
C11 C12 1.359(4) ?
C11 H11 0.93 ?
C12 H12 0.93 ?
O1W H1W 0.82(4) ?
O1W H2W 0.87(4) ?