#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202251.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_2202251
loop_
_publ_author_name
'Yamin, Bohari M.'
'Yusof, M. Sukeri M.'
_publ_section_title
;
 <i>N</i>-[<i>N</i>-(Furan-2-carbonyl)hydrazinothiocarbonyl]benzamide
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o124
_journal_page_last               o126
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C13 H11 N3 O3 S'
_chemical_formula_moiety         'C13 H11 N3 O3 S'
_chemical_formula_sum            'C13 H11 N3 O3 S'
_chemical_formula_weight         289.31
_chemical_name_systematic
;
N-[N-(Furan-2-carbonyl)-hydrazinocarbothioyl]-benzamide
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.375(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7902(14)
_cell_length_b                   7.5505(8)
_cell_length_c                   13.9952(15)
_cell_measurement_reflns_used    3018
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.6
_cell_volume                     1351.5(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART(Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      299(2)
_diffrn_detector_area_resol_mean 83.66
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type
;
Bruker SMART APEX CCD area-detector
;
_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  0.018
_diffrn_reflns_av_sigmaI/netI    0.023
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7854
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         1.6
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.25
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.862
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3065
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.057
_refine_ls_R_factor_gt           0.047
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0818P)^2^+0.2233P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.133
_refine_ls_wR_factor_ref         0.141
_reflns_number_gt                2548
_reflns_number_total             3065
_reflns_threshold_expression     I>2\s(I)'
_[local]_cod_data_source_file    ya6149.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Empirical'
changed to 'empirical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2202251
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_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_type_symbol
S1 0.32038(4) 0.11672(8) 0.43803(3) 0.0640(2) Uani d . 1 S
O1 -0.00052(10) 0.1927(2) 0.55967(9) 0.0622(4) Uani d . 1 O
O2 0.18606(10) 0.0735(2) 0.77269(9) 0.0585(4) Uani d . 1 O
O3 0.42788(12) -0.1285(2) 0.71557(11) 0.0678(4) Uani d . 1 O
N1 0.12097(10) 0.21639(19) 0.44317(9) 0.0443(3) Uani d . 1 N
H1A 0.1318 0.2538 0.3860 0.053 Uiso calc R 1 H
N2 0.18874(11) 0.0983(2) 0.58095(10) 0.0489(4) Uani d . 1 N
H2A 0.1286 0.1168 0.6062 0.059 Uiso calc R 1 H
N3 0.26738(12) 0.0221(2) 0.63375(11) 0.0539(4) Uani d . 1 N
H3A 0.3213 -0.0206 0.6055 0.065 Uiso calc R 1 H
C1 -0.04962(14) 0.3110(3) 0.31386(12) 0.0496(4) Uani d . 1 C
H1B 0.0098 0.2644 0.2853 0.059 Uiso calc R 1 H
C2 -0.12924(15) 0.3808(3) 0.25803(13) 0.0545(5) Uani d . 1 C
H2B -0.1236 0.3798 0.1918 0.065 Uiso calc R 1 H
C3 -0.21662(15) 0.4514(3) 0.29990(14) 0.0560(5) Uani d . 1 C
H3B -0.2696 0.4994 0.2622 0.067 Uiso calc R 1 H
C4 -0.22572(16) 0.4509(3) 0.39809(14) 0.0612(5) Uani d . 1 C
H4A -0.2848 0.4990 0.4264 0.073 Uiso calc R 1 H
C5 -0.14789(16) 0.3799(3) 0.45408(14) 0.0538(5) Uani d . 1 C
H5A -0.1551 0.3780 0.5202 0.065 Uiso calc R 1 H
C6 -0.05850(12) 0.3108(2) 0.41250(11) 0.0427(4) Uani d . 1 C
C7 0.02142(13) 0.2348(2) 0.47812(12) 0.0449(4) Uani d . 1 C
C8 0.20562(13) 0.1432(2) 0.49137(12) 0.0442(4) Uani d . 1 C
C9 0.26055(12) 0.0138(2) 0.72926(12) 0.0433(4) Uani d . 1 C
C10 0.34991(13) -0.0723(2) 0.77474(13) 0.0463(4) Uani d . 1 C
C11 0.37363(18) -0.1043(3) 0.86534(16) 0.0725(6) Uani d . 1 C
H11A 0.3335 -0.0793 0.9188 0.087 Uiso calc R 1 H
C12 0.47552(19) -0.1866(4) 0.8629(2) 0.0836(8) Uani d . 1 C
H12A 0.5144 -0.2253 0.9152 0.100 Uiso calc R 1 H
C13 0.5025(2) -0.1965(4) 0.7736(2) 0.0821(7) Uani d . 1 C
H13A 0.5653 -0.2442 0.7525 0.098 Uiso calc R 1 H
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 0.0465(3) 0.1028(5) 0.0427(3) 0.0105(2) 0.00506(19) -0.0016(2)
O1 0.0506(7) 0.0935(10) 0.0424(7) 0.0085(7) 0.0093(5) 0.0177(7)
O2 0.0460(7) 0.0837(9) 0.0459(7) 0.0121(6) 0.0024(5) -0.0071(6)
O3 0.0606(9) 0.0754(10) 0.0676(9) 0.0212(7) 0.0122(7) 0.0068(7)
N1 0.0424(7) 0.0573(8) 0.0334(7) -0.0010(6) 0.0023(5) 0.0018(6)
N2 0.0427(8) 0.0628(9) 0.0413(8) 0.0065(6) 0.0018(6) 0.0052(6)
N3 0.0507(8) 0.0696(10) 0.0414(8) 0.0157(7) 0.0020(6) 0.0029(7)
C1 0.0426(9) 0.0641(11) 0.0421(9) -0.0026(8) 0.0057(7) -0.0006(8)
C2 0.0527(10) 0.0722(12) 0.0387(9) -0.0033(9) 0.0004(7) 0.0044(8)
C3 0.0548(10) 0.0611(11) 0.0520(11) 0.0052(9) -0.0040(8) 0.0062(8)
C4 0.0549(11) 0.0719(13) 0.0569(12) 0.0154(9) 0.0059(8) -0.0002(9)
C5 0.0539(10) 0.0660(12) 0.0416(9) 0.0086(8) 0.0060(7) 0.0006(8)
C6 0.0418(8) 0.0456(9) 0.0406(9) -0.0043(7) 0.0030(6) 0.0005(7)
C7 0.0429(9) 0.0522(9) 0.0395(9) -0.0029(7) 0.0038(6) 0.0006(7)
C8 0.0461(9) 0.0496(9) 0.0370(8) -0.0029(7) -0.0003(6) -0.0047(7)
C9 0.0412(8) 0.0455(9) 0.0433(9) -0.0019(7) -0.0005(6) -0.0029(7)
C10 0.0416(8) 0.0508(9) 0.0465(9) 0.0007(7) 0.0027(7) 0.0019(7)
C11 0.0624(12) 0.1038(18) 0.0513(12) 0.0057(12) -0.0062(9) 0.0137(11)
C12 0.0659(14) 0.1033(19) 0.0813(17) 0.0148(13) -0.0197(12) 0.0285(14)
C13 0.0629(13) 0.0875(17) 0.096(2) 0.0265(12) 0.0056(12) 0.0216(14)
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
C13 O3 C10 105.60(18) yes
C7 N1 C8 126.13(14) yes
C7 N1 H1A 116.9 ?
C8 N1 H1A 116.9 ?
C8 N2 N3 119.77(14) yes
C8 N2 H2A 120.1 ?
N3 N2 H2A 120.1 ?
C9 N3 N2 120.29(14) yes
C9 N3 H3A 119.9 ?
N2 N3 H3A 119.9 ?
C2 C1 C6 119.88(16) ?
C2 C1 H1B 120.1 ?
C6 C1 H1B 120.1 ?
C3 C2 C1 120.32(17) ?
C3 C2 H2B 119.8 ?
C1 C2 H2B 119.8 ?
C2 C3 C4 119.90(17) ?
C2 C3 H3B 120.1 ?
C4 C3 H3B 120.1 ?
C5 C4 C3 120.27(18) ?
C5 C4 H4A 119.9 ?
C3 C4 H4A 119.9 ?
C4 C5 C6 120.27(17) ?
C4 C5 H5A 119.9 ?
C6 C5 H5A 119.9 ?
C1 C6 C5 119.35(16) ?
C1 C6 C7 123.78(15) ?
C5 C6 C7 116.84(15) ?
O1 C7 N1 121.75(16) yes
O1 C7 C6 121.19(14) ?
N1 C7 C6 117.05(14) yes
N2 C8 N1 115.66(14) yes
N2 C8 S1 123.14(13) ?
N1 C8 S1 121.20(12) ?
O2 C9 N3 122.36(15) yes
O2 C9 C10 124.06(16) ?
N3 C9 C10 113.58(14) ?
C11 C10 O3 111.08(17) ?
C11 C10 C9 132.35(18) ?
O3 C10 C9 116.54(15) ?
C10 C11 C12 104.9(2) ?
C10 C11 H11A 127.6 ?
C12 C11 H11A 127.6 ?
C13 C12 C11 107.0(2) ?
C13 C12 H12A 126.5 ?
C11 C12 H12A 126.5 ?
C12 C13 O3 111.4(2) ?
C12 C13 H13A 124.3 ?
O3 C13 H13A 124.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C8 1.6631(18) yes
O1 C7 1.219(2) yes
O2 C9 1.220(2) yes
O3 C10 1.368(2) yes
O3 C13 1.351(3) yes
N1 C7 1.374(2) yes
N1 C8 1.387(2) yes
N1 H1A 0.8600 ?
N2 N3 1.371(2) yes
N2 C8 1.318(2) yes
N2 H2A 0.8600 ?
N3 C9 1.342(2) yes
N3 H3A 0.8600 ?
C1 C2 1.384(3) ?
C1 C6 1.386(2) ?
C1 H1B 0.9300 ?
C2 C3 1.373(3) ?
C2 H2B 0.9300 ?
C3 C4 1.380(3) ?
C3 H3B 0.9300 ?
C4 C5 1.372(3) ?
C4 H4A 0.9300 ?
C5 C6 1.388(2) ?
C5 H5A 0.9300 ?
C6 C7 1.485(2) ?
C9 C10 1.457(2) ?
C10 C11 1.324(3) ?
C11 C12 1.444(3) ?
C11 H11A 0.9300 ?
C12 C13 1.300(4) ?
C12 H12A 0.9300 ?
C13 H13A 0.9300 ?
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
_geom_hbond_publ_flag
N1 H1A O2 4_565 0.86 2.17 2.988(2) 158 yes
N2 H2A O1 1_555 0.86 1.86 2.5395(19) 134 yes
N3 H3A S1 1_555 0.86 2.56 2.9148(16) 105 yes
N3 H3A O3 1_555 0.86 2.21 2.606(2) 108 yes
C1 H1B O2 4_565 0.93 2.57 3.194(2) 124 yes
C2 H2B O1 4_565 0.93 2.49 3.284(2) 143 yes
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
C8 N2 N3 C9 164.33(16)
C6 C1 C2 C3 0.7(3)
C1 C2 C3 C4 -0.8(3)
C2 C3 C4 C5 -0.1(3)
C3 C4 C5 C6 1.2(3)
C2 C1 C6 C5 0.4(3)
C2 C1 C6 C7 178.34(16)
C4 C5 C6 C1 -1.3(3)
C4 C5 C6 C7 -179.39(18)
C8 N1 C7 O1 3.2(3)
C8 N1 C7 C6 -177.63(15)
C1 C6 C7 O1 -159.43(18)
C5 C6 C7 O1 18.6(3)
C1 C6 C7 N1 21.4(2)
C5 C6 C7 N1 -160.64(16)
N3 N2 C8 N1 178.88(15)
N3 N2 C8 S1 -1.6(2)
C7 N1 C8 N2 -4.6(2)
C7 N1 C8 S1 175.93(14)
N2 N3 C9 O2 -0.5(3)
N2 N3 C9 C10 179.54(15)
C13 O3 C10 C11 -0.5(3)
C13 O3 C10 C9 177.71(18)
O2 C9 C10 C11 -0.9(3)
N3 C9 C10 C11 179.0(2)
O2 C9 C10 O3 -178.67(17)
N3 C9 C10 O3 1.2(2)
O3 C10 C11 C12 0.4(3)
C9 C10 C11 C12 -177.4(2)
C10 C11 C12 C13 -0.2(3)
C11 C12 C13 O3 -0.1(3)
C10 O3 C13 C12 0.4(3)