#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:48:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201957 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/27/2012767.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_2012767
loop_
_publ_author_name
'Forni, Alessandra'
'Gradinaru, Julieta'
_publ_section_title
;
 1-(1-Benzoylpropen-2-yl)-3-methylisothiosemicarbazide
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o342
_journal_page_last               o344
_journal_paper_doi               10.1107/S0108270102007059
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C12 H15 N3 O S'
_chemical_formula_moiety         'C12 H15 N3 O S'
_chemical_formula_sum            'C12 H15 N3 O S'
_chemical_formula_weight         249.33
_chemical_name_common
;
benzoylacetone S-methylisothiosemicarbazone
;
_chemical_name_systematic
;
1-(1-Benzoylpropen2-yl)-3-methylisothiosemicarbazide
;
_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           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 92.800(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9320(10)
_cell_length_b                   5.3240(10)
_cell_length_c                   26.316(2)
_cell_measurement_reflns_used    1875
_cell_measurement_temperature    288(2)
_cell_measurement_theta_max      23.05
_cell_measurement_theta_min      2.37
_cell_volume                     1249.9(3)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al.,1994)'
_diffrn_ambient_temperature      288(2)
_diffrn_measured_fraction_theta_full 0.901
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_device_type  'Bruker SMART Apex area-detector'
_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  0.036
_diffrn_reflns_av_sigmaI/netI    0.044
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            11930
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.55
_diffrn_standards_decay_%        0.00
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS in SAINT; Bruker, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.881
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2858
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.881
_refine_ls_R_factor_all          0.085
_refine_ls_R_factor_gt           0.050
_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/[σ²(Fo²)+(0.0866P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.140
_refine_ls_wR_factor_ref         0.151
_reflns_number_gt                1566
_reflns_number_total             2858
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            na1569.cif
_cod_data_source_block           I
_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.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2012767
_cod_database_fobs_code          2012767
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_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
_atom_site_type_symbol
S 0.72212(8) -0.11508(13) -0.11368(2) 0.0650(3) Uani d . 1 . . S
O 0.5825(2) -0.3019(3) 0.10011(7) 0.0680(5) Uani d . 1 . . O
N1 0.7209(2) -0.0502(4) 0.03292(7) 0.0580(5) Uani d . 1 . . N
H1 0.6639 -0.1750 0.0395 0.070 Uiso calc R 1 . . H
N2 0.7548(2) -0.0042(4) -0.01687(7) 0.0566(5) Uani d . 1 . . N
N3 0.5951(2) -0.3419(4) -0.03965(8) 0.0762(7) Uani d . 1 . . N
H3A 0.5746 -0.3761 -0.0088 0.091 Uiso calc R 1 . . H
H3B 0.5560 -0.4297 -0.0643 0.091 Uiso calc R 1 . . H
C1 0.6893(3) -0.1490(5) -0.04943(9) 0.0538(6) Uani d . 1 . . C
C2 0.5835(3) -0.1658(4) 0.18553(9) 0.0520(6) Uani d . 1 . . C
C3 0.6207(3) 0.0079(5) 0.22269(9) 0.0646(7) Uani d . 1 . . C
H3 0.6856 0.1384 0.2155 0.078 Uiso calc R 1 . . H
C4 0.5637(3) -0.0074(6) 0.27045(10) 0.0724(8) Uani d . 1 . . C
H4 0.5906 0.1116 0.2951 0.087 Uiso calc R 1 . . H
C5 0.6340(3) -0.1454(5) 0.13273(9) 0.0545(6) Uani d . 1 . . C
C6 0.7328(3) 0.0449(5) 0.11928(9) 0.0582(7) Uani d . 1 . . C
H6 0.7734 0.1461 0.1453 0.070 Uiso calc R 1 . . H
C7 0.7742(2) 0.0936(4) 0.07081(8) 0.0490(6) Uani d . 1 . . C
C8 0.8304(4) 0.1644(5) -0.11397(11) 0.0809(9) Uani d . 1 . . C
H8A 0.8556 0.2024 -0.1482 0.121 Uiso calc R 1 . . H
H8B 0.9207 0.1414 -0.0931 0.121 Uiso calc R 1 . . H
H8C 0.7736 0.3005 -0.1007 0.121 Uiso calc R 1 . . H
C9 0.4684(3) -0.1962(6) 0.28136(10) 0.0707(8) Uani d . 1 . . C
H9 0.4282 -0.2056 0.3132 0.085 Uiso calc R 1 . . H
C10 0.4321(3) -0.3720(6) 0.24518(11) 0.0796(9) Uani d . 1 . . C
H10 0.3674 -0.5021 0.2527 0.096 Uiso calc R 1 . . H
C11 0.4899(3) -0.3596(5) 0.19783(10) 0.0686(7) Uani d . 1 . . C
H11 0.4655 -0.4833 0.1739 0.082 Uiso calc R 1 . . H
C12 0.8779(3) 0.3000(5) 0.05865(10) 0.0705(8) Uani d . 1 . . C
H12A 0.8921 0.3016 0.0227 0.106 Uiso calc R 1 . . H
H12B 0.9727 0.2744 0.0767 0.106 Uiso calc R 1 . . H
H12C 0.8362 0.4576 0.0686 0.106 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
S 0.0756(5) 0.0696(5) 0.0507(4) 0.0015(4) 0.0124(3) 0.0033(3)
O 0.0780(12) 0.0660(11) 0.0608(10) -0.0115(10) 0.0122(9) -0.0128(9)
N1 0.0599(12) 0.0622(13) 0.0528(12) -0.0061(10) 0.0125(10) 0.0030(10)
N2 0.0589(12) 0.0620(13) 0.0493(11) -0.0024(11) 0.0076(10) 0.0007(10)
N3 0.0817(16) 0.0959(19) 0.0515(12) -0.0290(14) 0.0082(11) 0.0012(12)
C1 0.0480(13) 0.0602(15) 0.0539(14) 0.0026(12) 0.0087(11) 0.0038(12)
C2 0.0484(13) 0.0551(15) 0.0525(13) 0.0064(12) 0.0017(11) 0.0052(11)
C3 0.0710(17) 0.0646(16) 0.0594(16) -0.0080(14) 0.0144(13) -0.0016(13)
C4 0.0811(19) 0.0806(19) 0.0564(16) -0.0020(17) 0.0133(14) -0.0080(14)
C5 0.0533(14) 0.0558(15) 0.0542(14) 0.0048(12) 0.0012(11) -0.0030(12)
C6 0.0550(14) 0.0664(17) 0.0531(14) -0.0058(13) 0.0006(11) -0.0048(12)
C7 0.0452(12) 0.0529(14) 0.0485(13) -0.0007(11) -0.0016(10) -0.0016(11)
C8 0.110(2) 0.0616(18) 0.0737(19) -0.0069(17) 0.0291(17) 0.0084(14)
C9 0.0684(18) 0.088(2) 0.0565(16) 0.0040(16) 0.0118(14) 0.0127(15)
C10 0.078(2) 0.086(2) 0.0747(19) -0.0185(17) 0.0069(16) 0.0226(17)
C11 0.0791(19) 0.0664(17) 0.0599(16) -0.0144(15) 0.0005(14) 0.0057(13)
C12 0.0699(18) 0.0773(19) 0.0643(16) -0.0130(15) 0.0041(13) 0.0024(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
C1 S C8 102.05(13) no
C7 N1 N2 121.5(2) no
C7 N1 H1 119.2 no
N2 N1 H1 119.2 no
C1 N2 N1 114.6(2) no
C1 N3 H3A 120.0 no
C1 N3 H3B 120.0 no
H3A N3 H3B 120.0 no
N2 C1 N3 126.7(2) no
N2 C1 S 119.85(19) no
N3 C1 S 113.41(19) no
C3 C2 C11 117.7(2) no
C3 C2 C5 122.8(2) no
C11 C2 C5 119.4(2) no
C2 C3 C4 121.4(3) no
C2 C3 H3 119.3 no
C4 C3 H3 119.3 no
C9 C4 C3 119.9(3) no
C9 C4 H4 120.0 no
C3 C4 H4 120.0 no
O C5 C6 121.1(2) no
O C5 C2 117.9(2) no
C6 C5 C2 120.9(2) no
C7 C6 C5 125.1(2) no
C7 C6 H6 117.5 no
C5 C6 H6 117.5 no
N1 C7 C6 119.2(2) no
N1 C7 C12 118.1(2) no
C6 C7 C12 122.8(2) no
S C8 H8A 109.5 no
S C8 H8B 109.5 no
H8A C8 H8B 109.5 no
S C8 H8C 109.5 no
H8A C8 H8C 109.5 no
H8B C8 H8C 109.5 no
C4 C9 C10 119.4(3) no
C4 C9 H9 120.3 no
C10 C9 H9 120.3 no
C9 C10 C11 120.9(3) no
C9 C10 H10 119.5 no
C11 C10 H10 119.5 no
C10 C11 C2 120.6(3) no
C10 C11 H11 119.7 no
C2 C11 H11 119.7 no
C7 C12 H12A 109.5 no
C7 C12 H12B 109.5 no
H12A C12 H12B 109.5 no
C7 C12 H12C 109.5 no
H12A C12 H12C 109.5 no
H12B C12 H12C 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S C1 . 1.739(2) no
S C8 . 1.775(3) no
O C5 . 1.267(3) no
N1 C7 . 1.327(3) no
N1 N2 . 1.381(3) no
N1 H1 . 0.8600 no
N2 C1 . 1.274(3) no
N3 C1 . 1.361(3) no
N3 H3A . 0.8600 no
N3 H3B . 0.8600 no
C2 C3 . 1.375(3) no
C2 C11 . 1.377(3) no
C2 C5 . 1.486(3) no
C3 C4 . 1.381(3) no
C3 H3 . 0.9300 no
C4 C9 . 1.357(4) no
C4 H4 . 0.9300 no
C5 C6 . 1.400(3) no
C6 C7 . 1.370(3) no
C6 H6 . 0.9300 no
C7 C12 . 1.482(3) no
C8 H8A . 0.9600 no
C8 H8B . 0.9600 no
C8 H8C . 0.9600 no
C9 C10 . 1.363(4) no
C9 H9 . 0.9300 no
C10 C11 . 1.373(4) no
C10 H10 . 0.9300 no
C11 H11 . 0.9300 no
C12 H12A . 0.9600 no
C12 H12B . 0.9600 no
C12 H12C . 0.9600 no
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 H1 O . 0.86 1.91 2.581(3) 134 yes
N1 H1 N3 . 0.86 2.32 2.667(3) 104 yes
N3 H3A N1 . 0.86 2.40 2.667(3) 98 yes
C11 H11 O . 0.93 2.45 2.757(4) 99 yes
N3 H3B O 3_645 0.86 2.08 2.898(3) 157 yes
N3 H3A N3 3_645 0.86 2.52 3.228(4) 140 yes
C9 H9 S 4_556 0.93 2.89 3.751(3) 155 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21181801
