#------------------------------------------------------------------------------
#$Date: 2023-03-06 11:46:55 +0200 (Mon, 06 Mar 2023) $
#$Revision: 281661 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/68/8106841.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_8106841
loop_
_publ_author_name
'Meng-Xue, Wang'
'Zheng, Fang'
'Kai, Guo'
_publ_section_title
;
 Crystal structure of diethyl
 2-(((2-(pyridin-3-ylthio)phenyl)amino)methylene)malonate, C19H20N2O4S
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              249
_journal_page_last               250
_journal_paper_doi               10.1515/ncrs-2015-0108
_journal_volume                  231
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C19 H20 N2 O4 S'
_chemical_formula_sum            'C19 H20 N2 O4 S'
_chemical_formula_weight         372.43
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 106.10(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.983(4)
_cell_length_b                   5.0570(10)
_cell_length_c                   20.304(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     1872.7(7)
_computing_cell_refinement       'CAD4 EXPRESS(Enraf-Nonius, 1989)'
_computing_data_collection       'CAD4 EXPRESS(Enraf-Nonius, 1989)'
_computing_data_reduction        'XCAD4(Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL-PLUS (Sheldrick, 2008)'
_computing_publication_material  'SHELXL-97(Sheldrick, 2008)'
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_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  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0851
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            3539
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         1.12
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.9804
_exptl_absorpt_correction_T_min  0.9427
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews,1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3429
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1526
_refine_ls_R_factor_gt           0.0680
_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)+(0.0400P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1423
_reflns_number_gt                1574
_reflns_number_total             3429
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2015-0108_suppl.cif
_cod_data_source_block           x
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the built-in table derived from the
CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated
on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_cell_volume        1872.7(6)
_cod_original_sg_symbol_H-M      P21/C
_cod_database_code               8106841
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
S S 0.60035(6) 0.4549(2) 0.96832(6) 0.0711(4) Uani 1 1 d . . .
N1 N 0.70642(17) 0.3793(6) 0.88419(15) 0.0593(9) Uani 1 1 d . . .
H1A H 0.7072 0.4919 0.9161 0.071 Uiso 1 1 calc R . .
O1 O 0.89184(16) 0.8714(7) 0.94808(15) 0.0900(11) Uani 1 1 d U . .
C1 C 0.8238(2) 0.5425(8) 0.87637(17) 0.0519(10) Uani 1 1 d . . .
O2 O 0.78427(16) 0.7492(6) 0.96288(15) 0.0923(11) Uani 1 1 d . . .
C2 C 0.8311(2) 0.7276(9) 0.9318(2) 0.0676(12) Uani 1 1 d . . .
O3 O 0.94113(17) 0.6047(7) 0.85682(17) 0.1102(13) Uani 1 1 d . . .
C3 C 0.9014(3) 1.0698(10) 1.0056(2) 0.0902(16) Uani 1 1 d U . .
H3A H 0.9363 1.2059 1.0024 0.108 Uiso 1 1 calc R . .
H3B H 0.8551 1.1526 1.0047 0.108 Uiso 1 1 calc R . .
O4 O 0.86136(14) 0.3312(6) 0.79000(14) 0.0746(9) Uani 1 1 d . . .
C4 C 0.9284(3) 0.9159(11) 1.0667(2) 0.116(2) Uani 1 1 d . . .
H4A H 0.9363 1.0289 1.1061 0.174 Uiso 1 1 calc R . .
H4B H 0.9739 0.8337 1.0663 0.174 Uiso 1 1 calc R . .
H4C H 0.8932 0.7821 1.0687 0.174 Uiso 1 1 calc R . .
C5 C 0.8824(2) 0.5048(9) 0.8421(2) 0.0640(12) Uani 1 1 d . . .
C6 C 0.9151(2) 0.2571(10) 0.7557(2) 0.0875(15) Uani 1 1 d . . .
H6A H 0.9574 0.1789 0.7881 0.105 Uiso 1 1 calc R . .
H6B H 0.9312 0.4117 0.7356 0.105 Uiso 1 1 calc R . .
C7 C 0.8811(3) 0.0635(10) 0.7015(2) 0.0988(17) Uani 1 1 d . . .
H7A H 0.9163 0.0111 0.6779 0.148 Uiso 1 1 calc R . .
H7B H 0.8396 0.1430 0.6695 0.148 Uiso 1 1 calc R . .
H7C H 0.8655 -0.0889 0.7218 0.148 Uiso 1 1 calc R . .
C8 C 0.7632(2) 0.3840(8) 0.85689(18) 0.0558(11) Uani 1 1 d . . .
H8A H 0.7611 0.2674 0.8210 0.067 Uiso 1 1 calc R . .
C9 C 0.6458(2) 0.2076(8) 0.86555(19) 0.0558(11) Uani 1 1 d . . .
C10 C 0.6366(2) 0.0280(9) 0.8131(2) 0.0683(12) Uani 1 1 d . . .
H10A H 0.6714 0.0193 0.7888 0.082 Uiso 1 1 calc R . .
C11 C 0.5772(3) -0.1394(9) 0.7958(2) 0.0735(13) Uani 1 1 d . . .
H11A H 0.5724 -0.2616 0.7606 0.088 Uiso 1 1 calc R . .
C12 C 0.5247(2) -0.1246(9) 0.8313(2) 0.0738(13) Uani 1 1 d . . .
H12A H 0.4840 -0.2353 0.8199 0.089 Uiso 1 1 calc R . .
C13 C 0.5335(2) 0.0560(9) 0.8836(2) 0.0682(12) Uani 1 1 d . . .
H13A H 0.4982 0.0657 0.9074 0.082 Uiso 1 1 calc R . .
C14 C 0.5935(2) 0.2243(8) 0.90175(19) 0.0562(11) Uani 1 1 d . . .
C15 C 0.6428(2) 0.2639(8) 1.04182(19) 0.0547(11) Uani 1 1 d . . .
C16 C 0.6294(2) 0.3309(9) 1.1031(3) 0.0796(14) Uani 1 1 d . . .
H16A H 0.5971 0.4693 1.1030 0.096 Uiso 1 1 calc R . .
N2 N 0.6599(3) 0.2097(10) 1.1627(2) 0.0966(15) Uani 1 1 d . . .
C17 C 0.7043(3) 0.0106(12) 1.1610(2) 0.0921(16) Uani 1 1 d . . .
H17A H 0.7249 -0.0806 1.2015 0.111 Uiso 1 1 calc R . .
C18 C 0.7219(2) -0.0694(9) 1.1032(2) 0.0784(14) Uani 1 1 d . . .
H18A H 0.7547 -0.2075 1.1049 0.094 Uiso 1 1 calc R . .
C19 C 0.6903(2) 0.0572(9) 1.0430(2) 0.0660(12) Uani 1 1 d . . .
H19A H 0.7008 0.0042 1.0029 0.079 Uiso 1 1 calc R . .
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
C14 S C15 101.80(18) . .
C8 N1 C9 126.2(3) . .
C8 N1 H1A 116.9 . .
C9 N1 H1A 116.9 . .
C2 O1 C3 117.8(3) . .
C8 C1 C2 119.8(4) . .
C8 C1 C5 118.1(4) . .
C2 C1 C5 122.0(4) . .
O2 C2 O1 121.8(4) . .
O2 C2 C1 122.2(4) . .
O1 C2 C1 116.0(4) . .
C4 C3 O1 104.3(4) . .
C4 C3 H3A 110.9 . .
O1 C3 H3A 110.9 . .
C4 C3 H3B 110.9 . .
O1 C3 H3B 110.9 . .
H3A C3 H3B 108.9 . .
C5 O4 C6 117.1(3) . .
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C3 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
O3 C5 O4 121.9(4) . .
O3 C5 C1 127.2(4) . .
O4 C5 C1 110.8(4) . .
O4 C6 C7 108.2(4) . .
O4 C6 H6A 110.1 . .
C7 C6 H6A 110.1 . .
O4 C6 H6B 110.1 . .
C7 C6 H6B 110.1 . .
H6A C6 H6B 108.4 . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
N1 C8 C1 126.8(4) . .
N1 C8 H8A 116.6 . .
C1 C8 H8A 116.6 . .
C10 C9 C14 119.7(4) . .
C10 C9 N1 122.3(4) . .
C14 C9 N1 118.0(4) . .
C9 C10 C11 121.6(4) . .
C9 C10 H10A 119.2 . .
C11 C10 H10A 119.2 . .
C10 C11 C12 119.4(4) . .
C10 C11 H11A 120.3 . .
C12 C11 H11A 120.3 . .
C13 C12 C11 119.1(4) . .
C13 C12 H12A 120.4 . .
C11 C12 H12A 120.4 . .
C12 C13 C14 121.9(4) . .
C12 C13 H13A 119.1 . .
C14 C13 H13A 119.1 . .
C13 C14 C9 118.4(4) . .
C13 C14 S 119.3(3) . .
C9 C14 S 122.3(3) . .
C19 C15 C16 117.0(4) . .
C19 C15 S 124.8(3) . .
C16 C15 S 118.1(3) . .
N2 C16 C15 124.2(4) . .
N2 C16 H16A 117.9 . .
C15 C16 H16A 117.9 . .
C17 N2 C16 116.5(4) . .
N2 C17 C18 123.9(5) . .
N2 C17 H17A 118.0 . .
C18 C17 H17A 118.0 . .
C19 C18 C17 118.6(5) . .
C19 C18 H18A 120.7 . .
C17 C18 H18A 120.7 . .
C18 C19 C15 119.7(4) . .
C18 C19 H19A 120.1 . .
C15 C19 H19A 120.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S C14 1.763(4) .
S C15 1.773(4) .
N1 C8 1.342(4) .
N1 C9 1.408(4) .
N1 H1A 0.8600 .
O1 C2 1.326(5) .
O1 C3 1.512(5) .
C1 C8 1.368(5) .
C1 C2 1.441(5) .
C1 C5 1.478(5) .
O2 C2 1.229(4) .
O3 C5 1.184(4) .
C3 C4 1.433(6) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
O4 C5 1.348(4) .
O4 C6 1.435(4) .
C4 H4A 0.9600 .
C4 H4B 0.9600 .
C4 H4C 0.9600 .
C6 C7 1.480(5) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C8 H8A 0.9300 .
C9 C10 1.373(5) .
C9 C14 1.391(5) .
C10 C11 1.376(5) .
C10 H10A 0.9300 .
C11 C12 1.384(5) .
C11 H11A 0.9300 .
C12 C13 1.375(5) .
C12 H12A 0.9300 .
C13 C14 1.388(5) .
C13 H13A 0.9300 .
C15 C19 1.377(5) .
C15 C16 1.380(5) .
C16 N2 1.336(5) .
C16 H16A 0.9300 .
N2 C17 1.320(6) .
C17 C18 1.367(6) .
C17 H17A 0.9300 .
C18 C19 1.362(5) .
C18 H18A 0.9300 .
C19 H19A 0.9300 .
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
_geom_hbond_publ_flag
C19 H19A O2 0.93 2.36 3.141(5) 142 1_545 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C3 O1 C2 O2 -1.3(7) . . . .
C3 O1 C2 C1 179.5(3) . . . .
C8 C1 C2 O2 0.0(6) . . . .
C5 C1 C2 O2 -175.9(4) . . . .
C8 C1 C2 O1 179.2(4) . . . .
C5 C1 C2 O1 3.2(6) . . . .
C2 O1 C3 C4 82.0(5) . . . .
C6 O4 C5 O3 4.3(6) . . . .
C6 O4 C5 C1 -174.7(4) . . . .
C8 C1 C5 O3 -172.1(5) . . . .
C2 C1 C5 O3 4.0(7) . . . .
C8 C1 C5 O4 6.9(5) . . . .
C2 C1 C5 O4 -177.1(4) . . . .
C5 O4 C6 C7 179.1(4) . . . .
C9 N1 C8 C1 -177.2(4) . . . .
C2 C1 C8 N1 0.2(6) . . . .
C5 C1 C8 N1 176.4(4) . . . .
C8 N1 C9 C10 -3.2(6) . . . .
C8 N1 C9 C14 177.3(4) . . . .
C14 C9 C10 C11 -0.8(6) . . . .
N1 C9 C10 C11 179.6(4) . . . .
C9 C10 C11 C12 1.0(6) . . . .
C10 C11 C12 C13 -0.6(6) . . . .
C11 C12 C13 C14 0.1(6) . . . .
C12 C13 C14 C9 0.1(6) . . . .
C12 C13 C14 S 178.9(3) . . . .
C10 C9 C14 C13 0.3(6) . . . .
N1 C9 C14 C13 179.8(3) . . . .
C10 C9 C14 S -178.5(3) . . . .
N1 C9 C14 S 1.1(5) . . . .
C15 S C14 C13 85.8(3) . . . .
C15 S C14 C9 -95.4(3) . . . .
C14 S C15 C19 29.8(4) . . . .
C14 S C15 C16 -152.4(3) . . . .
C19 C15 C16 N2 0.5(7) . . . .
S C15 C16 N2 -177.5(4) . . . .
C15 C16 N2 C17 -1.3(7) . . . .
C16 N2 C17 C18 2.1(8) . . . .
N2 C17 C18 C19 -2.0(8) . . . .
C17 C18 C19 C15 1.0(7) . . . .
C16 C15 C19 C18 -0.3(6) . . . .
S C15 C19 C18 177.5(3) . . . .
