#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/38/2213801.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_2213801
loop_
_publ_author_name
'Sarojini, B. K.'
'Narayana, B.'
'Bindya, S.'
'Yathirajan, H. S.'
'Bolte, Michael'
_publ_section_title
;
 4-(Methylsulfanyl)benzaldehyde semicarbazone
;
_journal_coeditor_code           HB2410
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2946
_journal_page_last               o2946
_journal_paper_doi               10.1107/S1600536807023239
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C9 H11 N3 O S'
_chemical_formula_moiety         'C9 H11 N3 O S'
_chemical_formula_sum            'C9 H11 N3 O S'
_chemical_formula_weight         209.27
_chemical_name_systematic
;
4-(Methylthio)benzaldehyde semicarbazone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.494(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.1006(19)
_cell_length_b                   5.3082(7)
_cell_length_c                   13.0746(17)
_cell_measurement_reflns_used    5218
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.2
_cell_measurement_theta_min      3.3
_cell_volume                     999.5(2)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        X-AREA
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Stoe IPDS II two-circle'
_diffrn_measurement_method       ω
_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  0.0528
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7445
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.98
_diffrn_reflns_theta_min         2.83
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_T_max  0.884
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '[MULABS (Spek, 2003; Blessing, 1995)]'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.43
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.661
_refine_ls_extinction_coef       0.087(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2162
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0544
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0852P)²+0.4974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1514
_refine_ls_wR_factor_ref         0.1679
_reflns_number_gt                1678
_reflns_number_total             2162
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2410.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2213801
_cod_database_fobs_code          2213801
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N2 0.08441(13) -0.2424(3) 0.53704(18) 0.0462(5) Uani d D 1 . .
H H2 0.0655(18) -0.359(4) 0.4872(17) 0.051(7) Uiso d D 1 . .
S S1 0.42858(5) 0.66516(12) 0.32545(8) 0.0703(4) Uani d . 1 . .
O O1 0.00019(11) -0.4136(3) 0.63569(15) 0.0487(5) Uani d . 1 . .
N N1 0.13881(12) -0.0461(3) 0.52048(17) 0.0439(5) Uani d . 1 . .
N N3 0.07342(13) -0.0387(4) 0.68943(18) 0.0478(5) Uani d D 1 . .
H H3A 0.049(2) -0.017(7) 0.7422(19) 0.075(10) Uiso d D 1 . .
H H3B 0.1089(17) 0.078(4) 0.675(2) 0.057(8) Uiso d D 1 . .
C C1 0.15927(14) -0.0536(4) 0.4320(2) 0.0440(6) Uani d . 1 . .
H H1 0.1340 -0.1846 0.3823 0.053 Uiso calc R 1 . .
C C2 0.04991(14) -0.2357(4) 0.62250(19) 0.0426(6) Uani d . 1 . .
C C11 0.22026(14) 0.1332(4) 0.4052(2) 0.0424(5) Uani d . 1 . .
C C12 0.24456(15) 0.1058(4) 0.3108(2) 0.0477(6) Uani d . 1 A .
H H12 0.2182 -0.0281 0.2631 0.057 Uiso calc R 1 . .
C C13 0.30620(15) 0.2693(5) 0.2850(2) 0.0478(6) Uani d . 1 . .
H H13 0.3216 0.2469 0.2203 0.057 Uiso calc R 1 A .
C C14 0.34570(14) 0.4670(4) 0.3542(2) 0.0451(6) Uani d . 1 A .
C C15 0.32039(15) 0.4988(4) 0.4481(2) 0.0482(6) Uani d . 1 . .
H H15 0.3461 0.6340 0.4953 0.058 Uiso calc R 1 A .
C C16 0.25829(16) 0.3356(4) 0.4730(2) 0.0466(6) Uani d . 1 A .
H H16 0.2413 0.3611 0.5366 0.056 Uiso calc R 1 . .
C C17 0.4761(3) 0.8650(9) 0.4225(4) 0.0513(14) Uani d P 0.495(6) A 1
H H17A 0.5225 0.9672 0.4026 0.077 Uiso calc PR 0.495(6) A 1
H H17B 0.5063 0.7718 0.4885 0.077 Uiso calc PR 0.495(6) A 1
H H17C 0.4280 0.9752 0.4342 0.077 Uiso calc PR 0.495(6) A 1
C C17' 0.4006(4) 0.6638(12) 0.1996(5) 0.0642(17) Uani d P 0.505(6) A 2
H H17D 0.3337 0.6944 0.1701 0.096 Uiso calc PR 0.505(6) A 2
H H17E 0.4158 0.4998 0.1749 0.096 Uiso calc PR 0.505(6) A 2
H H17F 0.4347 0.7965 0.1754 0.096 Uiso calc PR 0.505(6) A 2
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 N2 N1 119.86(19)
C2 N2 H2 120.2(19)
N1 N2 H2 119.3(19)
C17' S1 C17 136.8(3)
C17' S1 C14 103.7(2)
C17 S1 C14 113.2(2)
C1 N1 N2 115.62(19)
C2 N3 H3A 121(2)
C2 N3 H3B 118(2)
H3A N3 H3B 121(3)
N1 C1 C11 122.2(2)
N1 C1 H1 118.9
C11 C1 H1 118.9
O1 C2 N3 123.5(2)
O1 C2 N2 119.0(2)
N3 C2 N2 117.5(2)
C12 C11 C16 118.2(2)
C12 C11 C1 119.5(2)
C16 C11 C1 122.3(2)
C13 C12 C11 121.6(2)
C13 C12 H12 119.2
C11 C12 H12 119.2
C12 C13 C14 120.0(2)
C12 C13 H13 120.0
C14 C13 H13 120.0
C13 C14 C15 118.8(2)
C13 C14 S1 120.2(2)
C15 C14 S1 120.93(17)
C16 C15 C14 120.8(2)
C16 C15 H15 119.6
C14 C15 H15 119.6
C15 C16 C11 120.5(3)
C15 C16 H16 119.7
C11 C16 H16 119.7
S1 C17 H17A 109.5
S1 C17 H17B 109.5
S1 C17 H17C 109.5
S1 C17' H17D 109.5
S1 C17' H17E 109.5
H17D C17' H17E 109.5
S1 C17' H17F 109.5
H17D C17' H17F 109.5
H17E C17' H17F 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N2 C2 1.368(3)
N2 N1 1.384(3)
N2 H2 0.881(10)
S1 C17' 1.571(6)
S1 C17 1.644(5)
S1 C14 1.760(2)
O1 C2 1.250(3)
N1 C1 1.285(3)
N3 C2 1.341(3)
N3 H3A 0.886(10)
N3 H3B 0.875(10)
C1 C11 1.466(3)
C1 H1 0.9500
C11 C12 1.397(4)
C11 C16 1.402(3)
C12 C13 1.386(4)
C12 H12 0.9500
C13 C14 1.397(3)
C13 H13 0.9500
C14 C15 1.401(4)
C15 C16 1.385(3)
C15 H15 0.9500
C16 H16 0.9500
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C17' H17D 0.9800
C17' H17E 0.9800
C17' H17F 0.9800
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
N2 H2 O1 3_546 0.881(10) 2.016(11) 2.886(3) 169(2)
N3 H3A O1 2_556 0.886(10) 2.025(12) 2.904(3) 171(4)
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
C2 N2 N1 C1 -172.28(18)
N2 N1 C1 C11 -176.76(17)
N1 N2 C2 O1 179.36(18)
N1 N2 C2 N3 -2.1(3)
N1 C1 C11 C12 175.99(19)
N1 C1 C11 C16 -1.7(3)
C16 C11 C12 C13 1.5(3)
C1 C11 C12 C13 -176.25(19)
C11 C12 C13 C14 0.1(3)
C12 C13 C14 C15 -1.3(3)
C12 C13 C14 S1 176.68(16)
C17' S1 C14 C13 29.8(3)
C17 S1 C14 C13 -173.2(2)
C17' S1 C14 C15 -152.3(3)
C17 S1 C14 C15 4.7(3)
C13 C14 C15 C16 0.9(3)
S1 C14 C15 C16 -177.06(16)
C14 C15 C16 C11 0.7(3)
C12 C11 C16 C15 -1.9(3)
C1 C11 C16 C15 175.80(19)
