#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/32/4023262.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_4023262
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         'C15 H11 N3 O S'
_chemical_formula_sum            'C15 H11 N3 O S'
_chemical_formula_weight         281.33
_chemical_name_systematic
; 
 ? 
;
_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                 90.6460(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0580(7)
_cell_length_b                   17.3093(14)
_cell_length_c                   9.3111(8)
_cell_measurement_temperature    295(1)
_cell_volume                     1298.61(19)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14185
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  0.9757
_exptl_absorpt_correction_T_min  0.9273
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            pale
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2819
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0561
_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)+(0.0669P)²+0.5427P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1339
_refine_ls_wR_factor_ref         0.1399
_reflns_number_gt                2351
_reflns_number_total             2819
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7022262-File005.cif
_cod_data_source_block           bashir3m
_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 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023262
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_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 0.2235(3) 0.43719(13) 0.2630(2) 0.0366(5) Uani 1 1 d . . .
C2 C 0.2664(3) 0.36924(13) 0.1951(2) 0.0384(5) Uani 1 1 d . . .
C3 C 0.3680(3) 0.31043(13) 0.2682(2) 0.0381(5) Uani 1 1 d . . .
C4 C 0.2074(3) 0.35780(13) 0.0525(2) 0.0427(5) Uani 1 1 d . . .
C5 C 0.5257(3) 0.19108(15) 0.2512(3) 0.0527(6) Uani 1 1 d . . .
H5A H 0.6146 0.2155 0.3035 0.079 Uiso 1 1 calc R . .
H5B H 0.5707 0.1604 0.1751 0.079 Uiso 1 1 calc R . .
H5C H 0.4640 0.1586 0.3148 0.079 Uiso 1 1 calc R . .
C6 C 0.2070(3) 0.52466(12) 0.4501(2) 0.0359(5) Uani 1 1 d . . .
C7 C 0.1148(3) 0.56395(12) 0.3483(2) 0.0367(5) Uani 1 1 d . . .
C8 C 0.0385(3) 0.63441(13) 0.3785(3) 0.0433(5) Uani 1 1 d . . .
H8 H -0.0246 0.6600 0.3090 0.052 Uiso 1 1 calc R . .
C9 C 0.0589(3) 0.66484(13) 0.5131(3) 0.0479(6) Uani 1 1 d . . .
H9 H 0.0087 0.7117 0.5352 0.058 Uiso 1 1 calc R . .
C10 C 0.1559(3) 0.62609(13) 0.6204(2) 0.0389(5) Uani 1 1 d . . .
C11 C 0.1740(3) 0.65635(15) 0.7599(3) 0.0516(6) Uani 1 1 d . . .
H11 H 0.1245 0.7033 0.7821 0.062 Uiso 1 1 calc R . .
C12 C 0.2626(4) 0.61818(17) 0.8629(3) 0.0561(7) Uani 1 1 d . . .
H12 H 0.2735 0.6392 0.9545 0.067 Uiso 1 1 calc R . .
C13 C 0.3368(3) 0.54775(16) 0.8314(3) 0.0539(7) Uani 1 1 d . . .
H13 H 0.3971 0.5222 0.9027 0.065 Uiso 1 1 calc R . .
C14 C 0.3230(3) 0.51532(14) 0.6987(3) 0.0454(6) Uani 1 1 d . . .
H14 H 0.3732 0.4681 0.6796 0.055 Uiso 1 1 calc R . .
C15 C 0.2311(3) 0.55446(13) 0.5892(2) 0.0377(5) Uani 1 1 d . . .
N1 N 0.2670(2) 0.45466(11) 0.3991(2) 0.0382(4) Uani 1 1 d . . .
H1N1 H 0.329(3) 0.4222(13) 0.451(2) 0.030(6) Uiso 1 1 d . . .
N2 N 0.1580(3) 0.34878(14) -0.0616(2) 0.0648(7) Uani 1 1 d . . .
N3 N 0.4171(3) 0.24951(11) 0.1910(2) 0.0443(5) Uani 1 1 d . . .
H1N3 H 0.392(4) 0.2467(16) 0.105(3) 0.058(9) Uiso 1 1 d . . .
O1 O 0.4068(2) 0.31747(9) 0.39743(16) 0.0454(4) Uani 1 1 d . . .
S1 S 0.10649(8) 0.51137(3) 0.18694(6) 0.0425(2) 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 124.0(2) . . ?
N1 C1 S1 110.62(16) . . ?
C2 C1 S1 125.42(17) . . ?
C1 C2 C4 117.7(2) . . ?
C1 C2 C3 121.26(19) . . ?
C4 C2 C3 121.1(2) . . ?
O1 C3 N3 121.6(2) . . ?
O1 C3 C2 120.8(2) . . ?
N3 C3 C2 117.6(2) . . ?
N2 C4 C2 179.2(3) . . ?
N3 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 N1 112.51(19) . . ?
C7 C6 C15 121.4(2) . . ?
N1 C6 C15 126.1(2) . . ?
C6 C7 C8 121.9(2) . . ?
C6 C7 S1 110.32(17) . . ?
C8 C7 S1 127.73(17) . . ?
C9 C8 C7 118.2(2) . . ?
C9 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
C8 C9 C10 121.3(2) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C11 C10 C15 118.5(2) . . ?
C11 C10 C9 121.4(2) . . ?
C15 C10 C9 120.0(2) . . ?
C12 C11 C10 121.2(2) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 120.0(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 121.5(2) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C15 119.3(2) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C6 C15 C10 117.2(2) . . ?
C6 C15 C14 123.4(2) . . ?
C10 C15 C14 119.4(2) . . ?
C1 N1 C6 115.43(19) . . ?
C1 N1 H1N1 120.4(14) . . ?
C6 N1 H1N1 124.2(14) . . ?
C3 N3 C5 121.6(2) . . ?
C3 N3 H1N3 120(2) . . ?
C5 N3 H1N3 118(2) . . ?
C1 S1 C7 91.08(10) . . ?
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 1.345(3) . ?
C1 C2 1.381(3) . ?
C1 S1 1.739(2) . ?
C2 C4 1.419(3) . ?
C2 C3 1.469(3) . ?
C3 O1 1.245(3) . ?
C3 N3 1.338(3) . ?
C4 N2 1.141(3) . ?
C5 N3 1.446(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.377(3) . ?
C6 N1 1.390(3) . ?
C6 C15 1.406(3) . ?
C7 C8 1.396(3) . ?
C7 S1 1.758(2) . ?
C8 C9 1.368(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.429(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.406(3) . ?
C10 C15 1.412(3) . ?
C11 C12 1.361(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.391(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.361(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.425(3) . ?
C14 H14 0.9300 . ?
N1 H1N1 0.89(2) . ?
N3 H1N3 0.82(3) . ?
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 0.82(3) 2.24(3) 2.970(3) 149(3) 4_565
N1 H1N1 O1 0.89(2) 1.98(2) 2.628(2) 128.4(19) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21196729
