#------------------------------------------------------------------------------
#$Date: 2024-04-19 07:41:10 +0300 (Fri, 19 Apr 2024) $
#$Revision: 291293 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/30/2023091.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2023091
loop_
_publ_author_name
'Madhan, Sundarasamy'
'NizamMohideen, Mohamed'
'Viswanathan, Vijayan'
'Karthik Ananth, Mani'
'Narasimhan, Srinivasan'
_publ_section_title
;
 Synthesis, crystal structure and Hirshfeld surface analysis of
 4-{(1E)-1-[(carbamothioylamino)imino]ethyl}phenyl propanoate
;
_journal_coeditor_code           WM5713
_journal_issue                   5
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989024003177
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C12 H15 N3 O2 S'
_chemical_formula_moiety         'C12 H15 N3 O2 S'
_chemical_formula_sum            'C12 H15 N3 O2 S'
_chemical_formula_weight         265.33
_chemical_name_systematic
;
4-[(1E)-1-[(Carbamothioylamino)imino]ethyl]phenyl propanoate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                82.891(2)
_cell_angle_beta                 87.004(4)
_cell_angle_gamma                74.172(2)
_cell_formula_units_Z            2
_cell_length_a                   5.77000(10)
_cell_length_b                   8.3069(2)
_cell_length_c                   14.6243(5)
_cell_measurement_reflns_used    8530
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.996
_cell_measurement_theta_min      1.403
_cell_volume                     669.07(3)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al.,
2020)
;
_computing_publication_material
;
WinGX (Farrugia, 2012), pubCIF (Westrip, 2010) and PLATON (Spek,
2020)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0839
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8530
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         1.403
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.863
_exptl_absorpt_correction_T_min  0.723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       Block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.261
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         8530
_refine_ls_number_restraints     197
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0654
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1179P)²+0.1922P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1994
_refine_ls_wR_factor_ref         0.2189
_reflns_number_gt                6376
_reflns_number_total             8530
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm5713.cif
_cod_data_source_block           I
_cod_database_code               2023091
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.934
_shelx_estimated_absorpt_t_max   0.954
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 1.0534(11) 0.1766(9) 0.6695(4) 0.0748(18) Uani d 1 . .
H H1A 1.177682 0.206605 0.699122 0.112 Uiso calc 1 . .
H H1B 1.105508 0.059493 0.660560 0.112 Uiso calc 1 . .
H H1C 0.909702 0.196951 0.707362 0.112 Uiso calc 1 . .
C C2 1.0027(10) 0.2796(8) 0.5790(3) 0.0627(16) Uani d 1 . .
H H2A 0.959090 0.397789 0.588404 0.075 Uiso calc 1 . .
H H2B 1.148613 0.257722 0.541123 0.075 Uiso calc 1 . .
C C3 0.8076(11) 0.2464(8) 0.5289(4) 0.0605(15) Uani d 1 . .
C C4 0.6029(8) 0.3302(7) 0.3831(3) 0.0460(12) Uani d 1 . .
C C5 0.4929(9) 0.2042(7) 0.3839(3) 0.0553(14) Uani d 1 . .
H H5 0.527970 0.112943 0.429410 0.066 Uiso calc 1 . .
C C6 0.3285(9) 0.2129(7) 0.3165(3) 0.0518(13) Uani d 1 . .
H H6 0.257115 0.125208 0.316087 0.062 Uiso calc 1 . .
C C7 0.2684(8) 0.3510(6) 0.2492(3) 0.0392(11) Uani d 1 . .
C C8 0.3902(8) 0.4745(7) 0.2493(3) 0.0443(12) Uani d 1 . .
H H8 0.359427 0.565770 0.203699 0.053 Uiso calc 1 . .
C C9 0.5552(8) 0.4633(7) 0.3159(3) 0.0463(12) Uani d 1 . .
H H9 0.634613 0.546995 0.315112 0.056 Uiso calc 1 . .
C C10 0.0799(8) 0.3681(6) 0.1809(3) 0.0402(11) Uani d 1 . .
C C11 0.0131(9) 0.2144(7) 0.1596(3) 0.0538(14) Uani d 1 . .
H H11A 0.138562 0.115539 0.179483 0.081 Uiso calc 1 . .
H H11B -0.007165 0.220584 0.094384 0.081 Uiso calc 1 . .
H H11C -0.134948 0.208693 0.191289 0.081 Uiso calc 1 . .
C C12 -0.3239(8) 0.7118(6) 0.0597(3) 0.0414(11) Uani d 1 . .
N N1 -0.0217(6) 0.5204(5) 0.1479(2) 0.0407(10) Uani d 1 . .
N N2 -0.2082(7) 0.5502(5) 0.0885(3) 0.0420(10) Uani d 1 . .
N N3 -0.2309(9) 0.8273(6) 0.0830(4) 0.0623(13) Uani d 1 . .
O O2 0.7779(6) 0.3338(5) 0.4461(2) 0.0654(12) Uani d 1 . .
S S1 -0.5771(2) 0.75787(17) -0.00106(11) 0.0586(5) Uani d 1 . .
O O1A 0.829(7) 0.0938(10) 0.527(2) 0.114(13) Uani d 0.27(2) A 1
O O1B 0.6526(17) 0.1802(15) 0.5647(4) 0.084(4) Uani d 0.73(2) A 2
H H2 -0.271(7) 0.483(5) 0.067(3) 0.035(13) Uiso d 1 . .
H H3A -0.280(9) 0.930(5) 0.061(3) 0.071(18) Uiso d 1 . .
H H3B -0.105(6) 0.803(6) 0.109(3) 0.051(15) Uiso d 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C3 C2 C1 . . 113.6(5) ?
C3 C2 H2A . . 108.8 ?
C1 C2 H2A . . 108.8 ?
C3 C2 H2B . . 108.8 ?
C1 C2 H2B . . 108.8 ?
H2A C2 H2B . . 107.7 ?
O1B C3 O2 . . 121.3(5) ?
O1A C3 O2 . . 113.3(14) ?
O1B C3 C2 . . 124.9(5) ?
O1A C3 C2 . . 113.1(12) ?
O2 C3 C2 . . 111.6(5) ?
C9 C4 C5 . . 120.6(4) ?
C9 C4 O2 . . 114.3(4) ?
C5 C4 O2 . . 125.1(5) ?
C4 C5 C6 . . 119.7(5) ?
C4 C5 H5 . . 120.2 ?
C6 C5 H5 . . 120.2 ?
C5 C6 C7 . . 121.0(5) ?
C5 C6 H6 . . 119.5 ?
C7 C6 H6 . . 119.5 ?
C8 C7 C6 . . 117.4(4) ?
C8 C7 C10 . . 120.9(4) ?
C6 C7 C10 . . 121.7(4) ?
C9 C8 C7 . . 120.9(5) ?
C9 C8 H8 . . 119.6 ?
C7 C8 H8 . . 119.6 ?
C4 C9 C8 . . 120.4(5) ?
C4 C9 H9 . . 119.8 ?
C8 C9 H9 . . 119.8 ?
N1 C10 C7 . . 114.6(4) ?
N1 C10 C11 . . 125.6(4) ?
C7 C10 C11 . . 119.7(4) ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
N3 C12 N2 . . 116.7(4) ?
N3 C12 S1 . . 122.8(4) ?
N2 C12 S1 . . 120.6(4) ?
C10 N1 N2 . . 119.1(4) ?
C12 N2 N1 . . 118.2(4) ?
C12 N2 H2 . . 111(3) ?
N1 N2 H2 . . 131(3) ?
C12 N3 H3A . . 122(4) ?
C12 N3 H3B . . 121(4) ?
H3A N3 H3B . . 115(4) ?
C3 O2 C4 . . 124.5(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.480(7) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C3 . 1.479(7) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 O1B . 1.234(8) ?
C3 O1A . 1.242(2) ?
C3 O2 . 1.327(6) ?
C4 C9 . 1.363(7) ?
C4 C5 . 1.362(7) ?
C4 O2 . 1.410(5) ?
C5 C6 . 1.386(6) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.394(7) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.393(6) ?
C7 C10 . 1.482(6) ?
C8 C9 . 1.375(6) ?
C8 H8 . 0.9300 ?
C9 H9 . 0.9300 ?
C10 N1 . 1.285(6) ?
C10 C11 . 1.502(7) ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 N3 . 1.305(6) ?
C12 N2 . 1.351(6) ?
C12 S1 . 1.679(4) ?
N1 N2 . 1.369(5) ?
N2 H2 . 0.84(3) ?
N3 H3A . 0.85(3) ?
N3 H3B . 0.80(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3B N1 . 0.80(3) 2.27(5) 2.588(6) 104(4) yes
C5 H5 O1B . 0.93 2.32 2.812(7) 112.5 yes
N2 H2 S1 2_465 0.84(3) 2.69(3) 3.525(4) 173(4) yes
N3 H3A S1 2_475 0.85(3) 2.55(3) 3.402(5) 177(5) yes
C11 H11B S1 2_465 0.96 2.77 3.452(5) 128.3 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 C2 C3 O1B . . . . 20.2(11) ?
C1 C2 C3 O1A . . . . -47(2) ?
C1 C2 C3 O2 . . . . -176.3(5) ?
C9 C4 C5 C6 . . . . -0.9(8) ?
O2 C4 C5 C6 . . . . -178.1(5) ?
C4 C5 C6 C7 . . . . -1.8(8) ?
C5 C6 C7 C8 . . . . 3.6(7) ?
C5 C6 C7 C10 . . . . -175.4(4) ?
C6 C7 C8 C9 . . . . -2.8(7) ?
C10 C7 C8 C9 . . . . 176.3(4) ?
C5 C4 C9 C8 . . . . 1.8(8) ?
O2 C4 C9 C8 . . . . 179.2(4) ?
C7 C8 C9 C4 . . . . 0.2(7) ?
C8 C7 C10 N1 . . . . -24.6(6) ?
C6 C7 C10 N1 . . . . 154.4(4) ?
C8 C7 C10 C11 . . . . 158.8(4) ?
C6 C7 C10 C11 . . . . -22.2(6) ?
C7 C10 N1 N2 . . . . -176.1(3) ?
C11 C10 N1 N2 . . . . 0.3(7) ?
N3 C12 N2 N1 . . . . 7.4(7) ?
S1 C12 N2 N1 . . . . -171.5(3) ?
C10 N1 N2 C12 . . . . 175.4(4) ?
O1B C3 O2 C4 . . . . -14.7(11) ?
O1A C3 O2 C4 . . . . 52(2) ?
C2 C3 O2 C4 . . . . -178.9(5) ?
C9 C4 O2 C3 . . . . 161.2(5) ?
C5 C4 O2 C3 . . . . -21.5(8) ?
