#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/32/4023265.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4023265
loop_
_publ_author_name
'Ahmad Basheer'
'Zvi Rappoport'
_publ_section_title
;
 A Rich Array of Reactions of Cyanomonothiocarbonylmalonamides
 RNHCSCH(CN)CONHR' and Their Thioenols RNHC(SH)=C(CN)CONHR'
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1386
_journal_page_last               1396
_journal_paper_doi               10.1021/jo7022262
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C10 H15 N3 O S'
_chemical_formula_sum            'C10 H15 N3 O S'
_chemical_formula_weight         225.31
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                86.3810(10)
_cell_angle_beta                 69.4090(10)
_cell_angle_gamma                85.5860(10)
_cell_formula_units_Z            2
_cell_length_a                   7.5503(5)
_cell_length_b                   8.2831(5)
_cell_length_c                   10.0876(7)
_cell_measurement_temperature    295(1)
_cell_volume                     588.38(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(1)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6618
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  0.9462
_exptl_absorpt_correction_T_min  0.9322
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.011(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2543
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0396
_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)+(0.0493P)²+0.2027P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1015
_reflns_number_gt                2385
_reflns_number_total             2543
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7022262-File008.cif
_cod_data_source_block           bashir2m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 
;
_cod_database_code               4023265
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.17244(19) 0.47290(16) 0.27347(14) 0.0297(3) Uani 1 1 d . . .
C2 C 0.0672(2) 0.34252(17) 0.27169(14) 0.0307(3) Uani 1 1 d . . .
C3 C 0.0164(2) 0.21272(16) 0.38005(15) 0.0315(3) Uani 1 1 d . . .
C4 C -0.0204(2) 0.34398(19) 0.16831(17) 0.0420(4) Uani 1 1 d . . .
C5 C 0.3072(2) 0.73980(18) 0.17912(17) 0.0408(4) Uani 1 1 d . . .
H5 H 0.2962 0.7610 0.2763 0.049 Uiso 1 1 calc R . .
C6 C 0.2256(3) 0.8883(2) 0.1192(2) 0.0578(5) Uani 1 1 d . . .
H6A H 0.2379 0.8708 0.0231 0.087 Uiso 1 1 calc R . .
H6B H 0.2933 0.9810 0.1214 0.087 Uiso 1 1 calc R . .
H6C H 0.0941 0.9070 0.1751 0.087 Uiso 1 1 calc R . .
C7 C 0.5143(3) 0.7022(3) 0.0942(2) 0.0621(5) Uani 1 1 d . . .
H7A H 0.5590 0.6058 0.1335 0.093 Uiso 1 1 calc R . .
H7B H 0.5867 0.7911 0.0979 0.093 Uiso 1 1 calc R . .
H7C H 0.5286 0.6860 -0.0025 0.093 Uiso 1 1 calc R . .
C8 C 0.2867(2) 0.26262(17) 0.45331(16) 0.0359(3) Uani 1 1 d . . .
C9 C 0.4450(3) 0.1708(2) 0.3410(2) 0.0568(5) Uani 1 1 d . . .
H9A H 0.4447 0.0575 0.3679 0.085 Uiso 1 1 calc R . .
H9B H 0.5646 0.2111 0.3324 0.085 Uiso 1 1 calc R . .
H9C H 0.4259 0.1857 0.2518 0.085 Uiso 1 1 calc R . .
C10 C 0.3191(3) 0.2558(2) 0.5947(2) 0.0525(5) Uani 1 1 d . . .
H10A H 0.2225 0.3226 0.6605 0.079 Uiso 1 1 calc R . .
H10B H 0.4412 0.2945 0.5808 0.079 Uiso 1 1 calc R . .
H10C H 0.3139 0.1460 0.6319 0.079 Uiso 1 1 calc R . .
N1 N 0.19342(19) 0.60125(15) 0.18408(14) 0.0362(3) Uani 1 1 d . . .
N2 N -0.0892(3) 0.3496(2) 0.0835(2) 0.0701(6) Uani 1 1 d . . .
H1N2 H 0.149(3) 0.600(2) 0.123(2) 0.042(5) Uiso 1 1 d . . .
N3 N 0.10441(18) 0.19820(15) 0.47667(14) 0.0359(3) Uani 1 1 d . . .
H1N3 H 0.087(3) 0.109(2) 0.524(2) 0.046(5) Uiso 1 1 d . . .
O1 O -0.10780(16) 0.11992(13) 0.38639(13) 0.0439(3) Uani 1 1 d . . .
S1 S 0.27601(6) 0.47800(4) 0.40283(4) 0.03851(15) Uani 1 1 d . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 123.51(13) . . ?
N1 C1 S1 116.41(11) . . ?
C2 C1 S1 120.02(10) . . ?
C1 C2 C4 118.83(12) . . ?
C1 C2 C3 125.14(12) . . ?
C4 C2 C3 115.47(12) . . ?
O1 C3 N3 120.54(12) . . ?
O1 C3 C2 121.02(12) . . ?
N3 C3 C2 118.41(12) . . ?
N2 C4 C2 177.98(16) . . ?
N1 C5 C7 110.99(14) . . ?
N1 C5 C6 108.75(14) . . ?
C7 C5 C6 112.14(15) . . ?
N1 C5 H5 108.3 . . ?
C7 C5 H5 108.3 . . ?
C6 C5 H5 108.3 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C9 111.32(14) . . ?
N3 C8 C10 108.25(13) . . ?
C9 C8 C10 111.83(14) . . ?
N3 C8 S1 109.00(10) . . ?
C9 C8 S1 110.96(12) . . ?
C10 C8 S1 105.27(11) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 N1 C5 125.57(13) . . ?
C1 N1 H1N2 117.7(14) . . ?
C5 N1 H1N2 116.5(14) . . ?
C3 N3 C8 123.59(12) . . ?
C3 N3 H1N3 113.0(13) . . ?
C8 N3 H1N3 114.1(12) . . ?
C1 S1 C8 100.41(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.3315(18) . ?
C1 C2 1.3940(19) . ?
C1 S1 1.7452(14) . ?
C2 C4 1.4169(19) . ?
C2 C3 1.4554(18) . ?
C3 O1 1.2395(17) . ?
C3 N3 1.3547(18) . ?
C4 N2 1.143(2) . ?
C5 N1 1.4737(18) . ?
C5 C7 1.514(3) . ?
C5 C6 1.520(2) . ?
C5 H5 0.9800 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 N3 1.4504(18) . ?
C8 C9 1.519(2) . ?
C8 C10 1.527(2) . ?
C8 S1 1.8277(15) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N1 H1N2 0.799(19) . ?
N3 H1N3 0.84(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H1N3 O1 0.84(2) 2.07(2) 2.8995(16) 167.3(17) 2_556
N1 H1N2 N2 0.799(19) 2.291(19) 3.062(2) 162.7(18) 2_565
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21120866
