#------------------------------------------------------------------------------
#$Date: 2016-02-21 11:56:54 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176809 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/00/2240056.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_2240056
loop_
_publ_author_name
'Vimala, G.'
'Govindaraj, J.'
'Haribabu, J.'
'Karvembu, C.'
'SubbiahPandi, A.'
_publ_section_title
;
 Crystal structure of
 (2E)-N-methyl-2-[(4-oxo-4H-chromen-3-yl)methylidene]hydrazinecarbothioamide
;
_journal_coeditor_code           HB7287
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1151
_journal_paper_doi               10.1107/S1600536814021667
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C12 H11 N3 O2 S'
_chemical_formula_moiety         'C12 H11 N3 O2 S'
_chemical_formula_sum            'C12 H11 N3 O2 S'
_chemical_formula_weight         261.30
_chemical_name_systematic
(2E)-N-Methyl-2-[(4-oxo-4H-chromen-3-yl)methylidene]hydrazinecarbothioamide
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.365(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.3702(7)
_cell_length_b                   20.647(2)
_cell_length_c                   9.2717(10)
_cell_measurement_temperature    293(2)
_cell_volume                     1206.5(2)
_computing_cell_refinement
;
SAINT (Bruker, 2008)
;
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'ω and φ scans'
_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  0.0311
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17429
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.15
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.244
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3560
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0427
_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)+(0.0560P)²+0.3687P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1313
_reflns_number_gt                2257
_reflns_number_total             3560
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7287sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2240056
_cod_database_fobs_code          2240056
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 1.1216(3) -0.01086(8) -0.30947(18) 0.0402(4) Uani d . 1 1
C C2 1.2628(3) -0.03414(11) -0.3973(2) 0.0536(5) Uani d . 1 1
H H2 1.3795 -0.0097 -0.4138 0.064 Uiso calc R 1 1
C C3 1.2268(4) -0.09395(12) -0.4591(2) 0.0615(6) Uani d . 1 1
H H3 1.3198 -0.1102 -0.5187 0.074 Uiso calc R 1 1
C C4 1.0550(4) -0.13046(11) -0.4344(2) 0.0590(6) Uani d . 1 1
H H4 1.0321 -0.1708 -0.4784 0.071 Uiso calc R 1 1
C C5 0.9167(3) -0.10774(9) -0.3453(2) 0.0485(5) Uani d . 1 1
H H5 0.8020 -0.1329 -0.3279 0.058 Uiso calc R 1 1
C C6 0.9493(3) -0.04658(8) -0.28081(17) 0.0359(4) Uani d . 1 1
C C7 0.8095(3) -0.02066(8) -0.18335(17) 0.0353(4) Uani d . 1 1
C C8 0.8552(3) 0.04523(7) -0.13502(17) 0.0336(3) Uani d . 1 1
C C9 1.0264(3) 0.07560(8) -0.1711(2) 0.0429(4) Uani d . 1 1
H H9 1.0518 0.1177 -0.1376 0.051 Uiso calc R 1 1
C C10 0.7153(3) 0.07618(8) -0.04415(18) 0.0373(4) Uani d . 1 1
H H10 0.5918 0.0552 -0.0274 0.045 Uiso calc R 1 1
C C11 0.6662(3) 0.21399(7) 0.16614(18) 0.0367(4) Uani d . 1 1
C C12 0.9249(4) 0.30201(10) 0.2112(3) 0.0619(6) Uani d . 1 1
H H12A 0.8427 0.3380 0.1689 0.093 Uiso calc R 1 1
H H12B 1.0703 0.3075 0.1976 0.093 Uiso calc R 1 1
H H12C 0.9158 0.2998 0.3136 0.093 Uiso calc R 1 1
N N1 0.7607(2) 0.13156(6) 0.01244(15) 0.0367(3) Uani d . 1 1
N N2 0.6206(2) 0.15691(6) 0.09629(16) 0.0400(3) Uani d . 1 1
H H2A 0.5048 0.1368 0.1046 0.048 Uiso calc R 1 1
N N3 0.8432(3) 0.24283(7) 0.14142(18) 0.0456(4) Uani d . 1 1
H H3A 0.9141 0.2252 0.0797 0.055 Uiso calc R 1 1
O O1 1.1633(2) 0.04988(6) -0.25169(15) 0.0482(3) Uani d . 1 1
O O2 0.6644(2) -0.05230(6) -0.14399(16) 0.0550(4) Uani d . 1 1
S S1 0.49924(9) 0.24309(2) 0.27366(6) 0.05253(18) Uani d . 1 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
O1 C1 C6 121.78(15)
O1 C1 C2 116.17(17)
C6 C1 C2 122.05(17)
C3 C2 C1 118.5(2)
C3 C2 H2 120.8
C1 C2 H2 120.8
C2 C3 C4 121.0(2)
C2 C3 H3 119.5
C4 C3 H3 119.5
C5 C4 C3 120.5(2)
C5 C4 H4 119.7
C3 C4 H4 119.7
C4 C5 C6 119.8(2)
C4 C5 H5 120.1
C6 C5 H5 120.1
C1 C6 C5 118.20(16)
C1 C6 C7 119.82(15)
C5 C6 C7 121.97(16)
O2 C7 C8 122.21(15)
O2 C7 C6 122.79(15)
C8 C7 C6 115.00(14)
C9 C8 C7 119.72(15)
C9 C8 C10 121.73(15)
C7 C8 C10 118.52(14)
O1 C9 C8 124.97(16)
O1 C9 H9 117.5
C8 C9 H9 117.5
N1 C10 C8 120.64(15)
N1 C10 H10 119.7
C8 C10 H10 119.7
N3 C11 N2 115.89(15)
N3 C11 S1 124.97(13)
N2 C11 S1 119.14(13)
N3 C12 H12A 109.5
N3 C12 H12B 109.5
H12A C12 H12B 109.5
N3 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C10 N1 N2 116.71(14)
C11 N2 N1 119.45(14)
C11 N2 H2A 120.3
N1 N2 H2A 120.3
C11 N3 C12 124.28(16)
C11 N3 H3A 117.9
C12 N3 H3A 117.9
C9 O1 C1 118.35(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.374(2)
C1 C6 1.380(2)
C1 C2 1.384(3)
C2 C3 1.367(3)
C2 H2 0.9300
C3 C4 1.375(3)
C3 H3 0.9300
C4 C5 1.375(3)
C4 H4 0.9300
C5 C6 1.400(2)
C5 H5 0.9300
C6 C7 1.459(2)
C7 O2 1.230(2)
C7 C8 1.449(2)
C8 C9 1.342(2)
C8 C10 1.460(2)
C9 O1 1.338(2)
C9 H9 0.9300
C10 N1 1.274(2)
C10 H10 0.9300
C11 N3 1.324(2)
C11 N2 1.356(2)
C11 S1 1.6715(17)
C12 N3 1.444(2)
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
N1 N2 1.3695(18)
N2 H2A 0.8600
N3 H3A 0.8600
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 H2A O2 3_655.01 0.86 2.11 2.897(2) 152
C10 H10 O2 3_655.01 0.93 2.44 3.219(2) 141
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
O1 C1 C2 C3 -179.09(17)
C6 C1 C2 C3 1.2(3)
C1 C2 C3 C4 -0.3(3)
C2 C3 C4 C5 -0.8(3)
C3 C4 C5 C6 0.9(3)
O1 C1 C6 C5 179.29(15)
C2 C1 C6 C5 -1.0(3)
O1 C1 C6 C7 -1.8(2)
C2 C1 C6 C7 177.85(16)
C4 C5 C6 C1 -0.1(3)
C4 C5 C6 C7 -178.91(17)
C1 C6 C7 O2 -173.71(17)
C5 C6 C7 O2 5.1(3)
C1 C6 C7 C8 5.8(2)
C5 C6 C7 C8 -175.36(16)
O2 C7 C8 C9 174.28(17)
C6 C7 C8 C9 -5.2(2)
O2 C7 C8 C10 -4.0(2)
C6 C7 C8 C10 176.46(14)
C7 C8 C9 O1 0.6(3)
C10 C8 C9 O1 178.80(16)
C9 C8 C10 N1 -5.1(3)
C7 C8 C10 N1 173.16(15)
C8 C10 N1 N2 -179.90(14)
N3 C11 N2 N1 3.0(2)
S1 C11 N2 N1 -177.53(12)
C10 N1 N2 C11 176.29(15)
N2 C11 N3 C12 -176.58(18)
S1 C11 N3 C12 4.0(3)
C8 C9 O1 C1 3.8(3)
C6 C1 O1 C9 -3.1(2)
C2 C1 O1 C9 177.22(16)
