#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/08/7150851.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_7150851
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         'C20 H21 N3 O S'
_chemical_formula_sum            'C20 H21 N3 O S'
_chemical_formula_weight         351.46
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 116.339(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.321(2)
_cell_length_b                   18.376(3)
_cell_length_c                   9.3465(16)
_cell_measurement_temperature    295(1)
_cell_volume                     1896.5(5)
_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 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  0.1157
_diffrn_reflns_av_sigmaI/netI    0.1722
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10385
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.9855
_exptl_absorpt_correction_T_min  0.9679
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         4082
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.940
_refine_ls_R_factor_all          0.1637
_refine_ls_R_factor_gt           0.0815
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0200P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1213
_reflns_number_gt                2061
_reflns_number_total             4082
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b717556f.txt
_cod_data_source_block           12v
_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_cell_volume        1896.5(6)
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               7150851
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -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 0.4755(5) 1.0233(3) 0.2978(6) 0.0342(13) Uani 1 1 d . . .
C2 C 0.5909(4) 1.0296(3) 0.4576(5) 0.0304(12) Uani 1 1 d . . .
H2 H 0.5673 1.0273 0.5448 0.037 Uiso 1 1 calc R . .
C3 C 0.6705(4) 0.9640(3) 0.4708(6) 0.0388(14) Uani 1 1 d . . .
C4 C 0.6504(5) 1.0994(4) 0.4668(6) 0.0440(15) Uani 1 1 d . . .
C5 C 0.2761(4) 0.9627(3) 0.1714(5) 0.0338(13) Uani 1 1 d . . .
H5 H 0.2397 1.0062 0.1074 0.041 Uiso 1 1 calc R . .
C6 C 0.2969(5) 0.9073(3) 0.0641(6) 0.0377(14) Uani 1 1 d . . .
C7 C 0.4029(5) 0.8688(3) 0.1099(6) 0.0427(15) Uani 1 1 d . . .
H7 H 0.4668 0.8774 0.2099 0.051 Uiso 1 1 calc R . .
C8 C 0.4167(7) 0.8173(3) 0.0098(8) 0.0622(18) Uani 1 1 d . . .
H8 H 0.4891 0.7919 0.0419 0.075 Uiso 1 1 calc R . .
C9 C 0.3212(8) 0.8047(4) -0.1375(9) 0.079(2) Uani 1 1 d . . .
H9 H 0.3286 0.7709 -0.2066 0.095 Uiso 1 1 calc R . .
C10 C 0.2147(8) 0.8426(4) -0.1819(8) 0.083(2) Uani 1 1 d . . .
H10 H 0.1497 0.8333 -0.2805 0.100 Uiso 1 1 calc R . .
C11 C 0.2027(6) 0.8937(3) -0.0833(6) 0.0579(18) Uani 1 1 d . . .
H11 H 0.1305 0.9193 -0.1163 0.070 Uiso 1 1 calc R . .
C12 C 0.1877(5) 0.9325(3) 0.2291(6) 0.0374(14) Uani 1 1 d . . .
C13 C 0.2229(5) 0.8756(3) 0.3392(7) 0.0486(16) Uani 1 1 d . . .
H13 H 0.3011 0.8570 0.3789 0.058 Uiso 1 1 calc R . .
C14 C 0.1420(6) 0.8467(3) 0.3894(7) 0.0592(18) Uani 1 1 d . . .
H14 H 0.1652 0.8085 0.4622 0.071 Uiso 1 1 calc R . .
C15 C 0.0281(6) 0.8746(4) 0.3312(8) 0.070(2) Uani 1 1 d . . .
H15 H -0.0258 0.8557 0.3665 0.084 Uiso 1 1 calc R . .
C16 C -0.0080(6) 0.9285(4) 0.2246(8) 0.072(2) Uani 1 1 d . . .
H16 H -0.0867 0.9461 0.1853 0.087 Uiso 1 1 calc R . .
C17 C 0.0710(5) 0.9581(3) 0.1723(7) 0.0602(19) Uani 1 1 d . . .
H17 H 0.0451 0.9958 0.0981 0.072 Uiso 1 1 calc R . .
C18 C 0.7067(7) 0.8373(3) 0.5685(8) 0.065(2) Uani 1 1 d . . .
H18 H 0.7173 0.8269 0.4726 0.078 Uiso 1 1 calc R . .
C19 C 0.8329(7) 0.8349(5) 0.7122(8) 0.108(3) Uani 1 1 d . . .
H19A H 0.8253 0.8432 0.8088 0.162 Uiso 1 1 calc R . .
H19B H 0.8833 0.8720 0.7004 0.162 Uiso 1 1 calc R . .
H19C H 0.8689 0.7881 0.7172 0.162 Uiso 1 1 calc R . .
C20 C 0.6236(8) 0.7824(3) 0.5779(8) 0.093(3) Uani 1 1 d . . .
H20A H 0.6055 0.7937 0.6653 0.140 Uiso 1 1 calc R . .
H20B H 0.6608 0.7353 0.5944 0.140 Uiso 1 1 calc R . .
H20C H 0.5501 0.7823 0.4801 0.140 Uiso 1 1 calc R . .
N1 N 0.3881(4) 0.9849(2) 0.3097(5) 0.0344(12) Uani 1 1 d . . .
H1N1 H 0.398(4) 0.964(3) 0.392(5) 0.041 Uiso 1 1 d . . .
N2 N 0.6954(5) 1.1545(3) 0.4818(7) 0.0688(17) Uani 1 1 d . . .
N3 N 0.6548(4) 0.9103(3) 0.5501(6) 0.0432(14) Uani 1 1 d . . .
H1N3 H 0.625(5) 0.912(3) 0.592(7) 0.052 Uiso 1 1 d . . .
O1 O 0.4701(3) 1.04650(18) 0.1715(4) 0.0376(10) Uani 1 1 d . . .
S1 S 0.75625(13) 0.96251(9) 0.37685(15) 0.0575(5) 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
O1 C1 N1 124.2(5) . . ?
O1 C1 C2 122.6(5) . . ?
N1 C1 C2 112.9(4) . . ?
C4 C2 C3 113.6(4) . . ?
C4 C2 C1 110.2(4) . . ?
C3 C2 C1 107.6(4) . . ?
C4 C2 H2 108.4 . . ?
C3 C2 H2 108.4 . . ?
C1 C2 H2 108.4 . . ?
N3 C3 C2 113.1(4) . . ?
N3 C3 S1 125.8(4) . . ?
C2 C3 S1 120.8(4) . . ?
N2 C4 C2 175.8(6) . . ?
N1 C5 C12 109.3(4) . . ?
N1 C5 C6 113.4(4) . . ?
C12 C5 C6 110.2(4) . . ?
N1 C5 H5 107.9 . . ?
C12 C5 H5 107.9 . . ?
C6 C5 H5 107.9 . . ?
C11 C6 C7 118.7(5) . . ?
C11 C6 C5 117.9(5) . . ?
C7 C6 C5 123.4(5) . . ?
C6 C7 C8 121.5(5) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C9 C8 C7 118.7(6) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C10 C9 C8 119.6(7) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C10 C9 121.1(7) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C6 120.3(6) . . ?
C10 C11 H11 119.8 . . ?
C6 C11 H11 119.8 . . ?
C17 C12 C13 118.1(5) . . ?
C17 C12 C5 121.9(5) . . ?
C13 C12 C5 119.9(5) . . ?
C14 C13 C12 120.2(5) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 119.4(6) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C16 C15 C14 121.4(6) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 120.3(7) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C16 120.5(6) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
N3 C18 C20 110.9(6) . . ?
N3 C18 C19 110.4(6) . . ?
C20 C18 C19 112.9(6) . . ?
N3 C18 H18 107.5 . . ?
C20 C18 H18 107.5 . . ?
C19 C18 H18 107.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 N1 C5 123.5(4) . . ?
C1 N1 H1N1 122(4) . . ?
C5 N1 H1N1 113(4) . . ?
C3 N3 C18 126.5(5) . . ?
C3 N3 H1N3 125(6) . . ?
C18 N3 H1N3 109(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 O1 1.228(5) . ?
C1 N1 1.333(6) . ?
C1 C2 1.543(6) . ?
C2 C4 1.460(7) . ?
C2 C3 1.524(6) . ?
C2 H2 0.9800 . ?
C3 N3 1.300(7) . ?
C3 S1 1.646(5) . ?
C4 N2 1.133(6) . ?
C5 N1 1.469(6) . ?
C5 C12 1.520(6) . ?
C5 C6 1.527(7) . ?
C5 H5 0.9800 . ?
C6 C11 1.375(7) . ?
C6 C7 1.377(7) . ?
C7 C8 1.393(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.378(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.377(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.368(8) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C17 1.377(7) . ?
C12 C13 1.394(6) . ?
C13 C14 1.383(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.361(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.333(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(8) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 N3 1.464(7) . ?
C18 C20 1.468(8) . ?
C18 C19 1.540(9) . ?
C18 H18 0.9800 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N1 H1N1 0.82(4) . ?
N3 H1N3 0.65(5) . ?
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 0.65(5) 2.45(5) 3.064(5) 158(7) 2_575
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190256
