#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/08/7150849.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_7150849
loop_
_publ_author_name
'Basheer, Ahmad'
'Rappoport, Zvi'
_publ_section_title
;
 Enols and thioenols of substituted cyanomonothiocarbonylmalonamides:
 structures, enolization vs. thioenolization, equilibria and
 conformations
;
_journal_issue                   6
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              1071
_journal_page_last               1082
_journal_paper_doi               10.1039/b717556f
_journal_volume                  6
_journal_year                    2008
_chemical_formula_moiety         'C10 H16 N3 S2, C7 H10 N3 O S, H2 O'
_chemical_formula_sum            'C17 H28 N6 O2 S3'
_chemical_formula_weight         444.63
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4053(5)
_cell_length_b                   14.8272(9)
_cell_length_c                   18.2296(11)
_cell_measurement_temperature    293(1)
_cell_volume                     2271.9(2)
_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      293(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            26066
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.351
_exptl_absorpt_correction_T_max  0.9268
_exptl_absorpt_correction_T_min  0.9113
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         4961
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0309
_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)+(0.0436P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0689
_refine_ls_wR_factor_ref         0.0697
_reflns_number_gt                4629
_reflns_number_total             4961
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b717556f.txt
_cod_data_source_block           12r
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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      P2(1)2(1)2(1)
_cod_database_code               7150849
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
C3 C 0.40712(18) 0.48399(11) 0.98794(9) 0.0332(3) Uani 1 1 d . . .
C2 C 0.56076(19) 0.49101(10) 1.02044(8) 0.0332(3) Uani 1 1 d . . .
C1 C 0.70853(19) 0.49773(12) 0.98009(9) 0.0390(4) Uani 1 1 d . . .
C4 C 0.57182(18) 0.49508(10) 1.09802(9) 0.0338(3) Uani 1 1 d . . .
C5 C 0.2521(2) 0.49398(14) 0.87145(10) 0.0454(4) Uani 1 1 d . . .
H5 H 0.182(3) 0.4579(13) 0.8935(10) 0.045(5) Uiso 1 1 d . . .
C6 C 0.1862(4) 0.58868(19) 0.87067(18) 0.0702(7) Uani 1 1 d . . .
H6A H 0.096(3) 0.5880(15) 0.8385(13) 0.068(7) Uiso 1 1 d . . .
H6B H 0.261(3) 0.6278(19) 0.8526(15) 0.089(9) Uiso 1 1 d . . .
H6C H 0.161(4) 0.6081(19) 0.9181(17) 0.094(10) Uiso 1 1 d . . .
C7 C 0.2869(4) 0.4597(3) 0.79482(13) 0.0708(7) Uani 1 1 d . . .
H7A H 0.189(4) 0.469(2) 0.7617(17) 0.104(9) Uiso 1 1 d . . .
H7B H 0.326(4) 0.405(2) 0.7977(15) 0.084(10) Uiso 1 1 d . . .
H7C H 0.372(3) 0.4895(16) 0.7720(12) 0.065(7) Uiso 1 1 d . . .
C11 C 0.4617(2) 0.76840(11) 0.77990(9) 0.0360(4) Uani 1 1 d . . .
C12 C 0.3992(2) 0.72685(11) 0.71703(9) 0.0350(4) Uani 1 1 d . . .
C13 C 0.2586(2) 0.76205(10) 0.68699(9) 0.0360(3) Uani 1 1 d . . .
C14 C 0.47954(19) 0.65336(12) 0.68306(9) 0.0366(4) Uani 1 1 d . . .
C15 C 0.6535(3) 0.79158(13) 0.88088(10) 0.0476(4) Uani 1 1 d . . .
H15 H 0.624(2) 0.8548(14) 0.8771(11) 0.054(6) Uiso 1 1 d . . .
C16 C 0.5862(6) 0.7462(3) 0.94724(16) 0.0886(10) Uani 1 1 d . . .
H16A H 0.624(3) 0.7757(19) 0.9873(17) 0.087(9) Uiso 1 1 d . . .
H16B H 0.626(4) 0.689(2) 0.9519(16) 0.090(11) Uiso 1 1 d . . .
H16C H 0.492(4) 0.743(3) 0.9452(18) 0.116(15) Uiso 1 1 d . . .
C17 C 0.8323(3) 0.7947(2) 0.87922(17) 0.0678(7) Uani 1 1 d . . .
H17A H 0.873(3) 0.8283(18) 0.9214(15) 0.087(8) Uiso 1 1 d . . .
H17B H 0.868(3) 0.7379(19) 0.8828(14) 0.081(9) Uiso 1 1 d . . .
H17C H 0.868(4) 0.813(2) 0.834(2) 0.122(13) Uiso 1 1 d . . .
C18 C 0.0433(2) 0.77808(12) 0.59627(10) 0.0417(4) Uani 1 1 d . . .
H18 H 0.055(2) 0.8432(12) 0.6065(9) 0.040(5) Uiso 1 1 d . . .
C19 C -0.1072(3) 0.74447(17) 0.63211(15) 0.0566(5) Uani 1 1 d . . .
H19A H -0.104(3) 0.7421(16) 0.6865(14) 0.074(8) Uiso 1 1 d . . .
H19B H -0.192(3) 0.7764(16) 0.6146(12) 0.062(6) Uiso 1 1 d . . .
H19C H -0.127(3) 0.6805(18) 0.6162(14) 0.081(8) Uiso 1 1 d . . .
C20 C 0.0441(3) 0.76535(19) 0.51421(12) 0.0585(5) Uani 1 1 d . . .
H20A H 0.019(4) 0.701(2) 0.4995(17) 0.109(11) Uiso 1 1 d . . .
H20B H 0.139(3) 0.7930(16) 0.4943(14) 0.066(7) Uiso 1 1 d . . .
H20C H -0.044(3) 0.7984(16) 0.4935(13) 0.066(7) Uiso 1 1 d . . .
N3 N 0.39655(18) 0.48927(12) 0.91511(8) 0.0441(4) Uani 1 1 d . . .
H1N3 H 0.478(2) 0.4956(12) 0.8917(10) 0.035(5) Uiso 1 1 d . . .
N2 N 0.59264(18) 0.49964(10) 1.16018(8) 0.0442(3) Uani 1 1 d . . .
N1 N 0.8448(2) 0.50507(13) 1.01781(10) 0.0503(4) Uani 1 1 d . . .
H1N1 H 0.847(3) 0.4887(14) 1.0609(11) 0.049(6) Uiso 1 1 d . . .
H2N1 H 0.926(3) 0.5029(12) 0.9953(11) 0.037(5) Uiso 1 1 d . . .
N4 N 0.5444(2) 0.59478(11) 0.65589(9) 0.0542(4) Uani 1 1 d . . .
N5 N 0.59375(19) 0.74673(11) 0.81362(8) 0.0406(3) Uani 1 1 d . . .
H1N5 H 0.644(2) 0.7039(13) 0.7986(10) 0.037(5) Uiso 1 1 d . . .
N6 N 0.18533(18) 0.73356(10) 0.62794(8) 0.0391(3) Uani 1 1 d . . .
H1N6 H 0.209(3) 0.6836(15) 0.6085(12) 0.059(6) Uiso 1 1 d . . .
O1 O 0.71338(15) 0.49817(12) 0.91140(7) 0.0609(4) Uani 1 1 d . . .
O1W O 0.7882(2) 0.59960(12) 0.78997(9) 0.0593(4) Uani 1 1 d . . .
H1W H 0.773(3) 0.5681(18) 0.8193(15) 0.070(9) Uiso 1 1 d . . .
H2W H 0.816(3) 0.5701(16) 0.7526(14) 0.062(7) Uiso 1 1 d . . .
S1 S 0.24191(5) 0.46824(3) 1.04145(2) 0.03886(11) Uani 1 1 d . . .
S2 S 0.34997(6) 0.85835(3) 0.81417(3) 0.04743(12) Uani 1 1 d . . .
S3 S 0.17737(6) 0.85354(3) 0.73401(3) 0.04460(12) 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
N3 C3 C2 118.06(14) . . ?
N3 C3 S1 121.42(13) . . ?
C2 C3 S1 120.52(12) . . ?
C4 C2 C3 118.50(14) . . ?
C4 C2 C1 116.59(14) . . ?
C3 C2 C1 124.86(14) . . ?
O1 C1 N1 118.98(15) . . ?
O1 C1 C2 122.44(15) . . ?
N1 C1 C2 118.58(15) . . ?
N2 C4 C2 174.90(17) . . ?
N3 C5 C6 110.89(18) . . ?
N3 C5 C7 109.13(19) . . ?
C6 C5 C7 112.0(2) . . ?
N3 C5 H5 106.0(13) . . ?
C6 C5 H5 108.6(13) . . ?
C7 C5 H5 110.0(12) . . ?
C5 C6 H6A 106.6(14) . . ?
C5 C6 H6B 109.8(18) . . ?
H6A C6 H6B 109(2) . . ?
C5 C6 H6C 111.1(18) . . ?
H6A C6 H6C 113(2) . . ?
H6B C6 H6C 107(3) . . ?
C5 C7 H7A 110.0(17) . . ?
C5 C7 H7B 109.1(19) . . ?
H7A C7 H7B 117(3) . . ?
C5 C7 H7C 113.5(14) . . ?
H7A C7 H7C 107(2) . . ?
H7B C7 H7C 100(2) . . ?
N5 C11 C12 126.39(16) . . ?
N5 C11 S2 118.39(13) . . ?
C12 C11 S2 115.22(13) . . ?
C11 C12 C13 118.08(15) . . ?
C11 C12 C14 120.91(15) . . ?
C13 C12 C14 120.96(15) . . ?
N6 C13 C12 126.62(15) . . ?
N6 C13 S3 118.09(13) . . ?
C12 C13 S3 115.29(13) . . ?
N4 C14 C12 179.7(2) . . ?
N5 C15 C16 109.82(19) . . ?
N5 C15 C17 109.60(18) . . ?
C16 C15 C17 114.1(3) . . ?
N5 C15 H15 106.7(12) . . ?
C16 C15 H15 113.2(12) . . ?
C17 C15 H15 103.0(12) . . ?
C15 C16 H16A 107.5(19) . . ?
C15 C16 H16B 111(2) . . ?
H16A C16 H16B 104(3) . . ?
C15 C16 H16C 112(3) . . ?
H16A C16 H16C 115(3) . . ?
H16B C16 H16C 108(4) . . ?
C15 C17 H17A 110.6(16) . . ?
C15 C17 H17B 107.9(18) . . ?
H17A C17 H17B 108(2) . . ?
C15 C17 H17C 111(2) . . ?
H17A C17 H17C 116(3) . . ?
H17B C17 H17C 103(3) . . ?
N6 C18 C20 109.11(16) . . ?
N6 C18 C19 111.09(16) . . ?
C20 C18 C19 113.09(19) . . ?
N6 C18 H18 106.5(11) . . ?
C20 C18 H18 108.0(10) . . ?
C19 C18 H18 108.8(11) . . ?
C18 C19 H19A 114.8(15) . . ?
C18 C19 H19B 109.4(15) . . ?
H19A C19 H19B 113(2) . . ?
C18 C19 H19C 108.9(15) . . ?
H19A C19 H19C 105(2) . . ?
H19B C19 H19C 105(2) . . ?
C18 C20 H20A 112.4(18) . . ?
C18 C20 H20B 108.9(15) . . ?
H20A C20 H20B 118(2) . . ?
C18 C20 H20C 108.6(14) . . ?
H20A C20 H20C 102(2) . . ?
H20B C20 H20C 105.8(19) . . ?
C3 N3 C5 127.15(16) . . ?
C3 N3 H1N3 118.1(13) . . ?
C5 N3 H1N3 114.4(13) . . ?
C1 N1 H1N1 119.0(16) . . ?
C1 N1 H2N1 117.8(14) . . ?
H1N1 N1 H2N1 117(2) . . ?
C11 N5 C15 124.44(16) . . ?
C11 N5 H1N5 118.4(13) . . ?
C15 N5 H1N5 117.1(13) . . ?
C13 N6 C18 123.73(15) . . ?
C13 N6 H1N6 121.2(15) . . ?
C18 N6 H1N6 114.6(15) . . ?
C1 O1 H1N3 98.4(5) . . ?
C1 O1 H1W 146.6(8) . . ?
H1N3 O1 H1W 95.9(9) . . ?
H1N5 O1W H1W 110(2) . . ?
H1N5 O1W H2W 129.9(16) . . ?
H1W O1W H2W 108(3) . . ?
C11 S2 S3 95.66(6) . . ?
C13 S3 S2 95.74(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
C3 N3 1.333(2) . ?
C3 C2 1.425(2) . ?
C3 S1 1.7131(16) . ?
C2 C4 1.418(2) . ?
C2 C1 1.447(2) . ?
C1 O1 1.253(2) . ?
C1 N1 1.340(2) . ?
C4 N2 1.149(2) . ?
C5 N3 1.453(2) . ?
C5 C6 1.510(3) . ?
C5 C7 1.515(3) . ?
C5 H5 0.89(2) . ?
C6 H6A 0.96(3) . ?
C6 H6B 0.92(3) . ?
C6 H6C 0.93(3) . ?
C7 H7A 1.03(3) . ?
C7 H7B 0.88(3) . ?
C7 H7C 0.94(3) . ?
C11 N5 1.309(2) . ?
C11 C12 1.403(2) . ?
C11 S2 1.7467(17) . ?
C12 C13 1.403(2) . ?
C12 C14 1.424(2) . ?
C13 N6 1.310(2) . ?
C13 S3 1.7438(16) . ?
C14 N4 1.139(2) . ?
C15 N5 1.483(2) . ?
C15 C16 1.495(4) . ?
C15 C17 1.504(3) . ?
C15 H15 0.97(2) . ?
C16 H16A 0.91(3) . ?
C16 H16B 0.91(3) . ?
C16 H16C 0.80(4) . ?
C17 H17A 0.98(3) . ?
C17 H17B 0.90(3) . ?
C17 H17C 0.91(4) . ?
C18 N6 1.481(2) . ?
C18 C20 1.508(3) . ?
C18 C19 1.508(3) . ?
C18 H18 0.989(18) . ?
C19 H19A 0.99(2) . ?
C19 H19B 0.91(3) . ?
C19 H19C 1.01(3) . ?
C20 H20A 1.01(3) . ?
C20 H20B 0.97(3) . ?
C20 H20C 0.97(3) . ?
N3 H1N3 0.82(2) . ?
N1 H1N1 0.82(2) . ?
N1 H2N1 0.80(2) . ?
N5 H1N5 0.81(2) . ?
N6 H1N6 0.84(2) . ?
O1 H1N3 2.01(2) . ?
O1 H1W 2.04(3) . ?
O1W H1N5 1.97(2) . ?
O1W H1W 0.72(3) . ?
O1W H2W 0.84(3) . ?
S2 S3 2.0604(7) . ?
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(2) 2.01(2) 2.6672(19) 137.7(17) .
N1 H1N1 N4 0.82(2) 2.32(2) 3.065(2) 152(2) 2_665
N1 H2N1 S1 0.80(2) 2.83(2) 3.4098(17) 131.2(17) 1_655
N5 H1N5 O1W 0.81(2) 1.97(2) 2.760(2) 164.2(18) .
N6 H1N6 S1 0.84(2) 2.59(2) 3.4368(16) 175(2) 2_564
O1W H1W O1 0.72(3) 2.04(3) 2.749(2) 170(3) .
O1W H2W N2 0.84(3) 2.12(3) 2.961(2) 174(2) 2_664
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653411
