#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/86/7218647.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_7218647
loop_
_publ_author_name
'Prabhu, Kandikere Ramaiah'
'Varun, Begur Vasanthkumar'
'Sood, Ankush'
_publ_section_title
;
 A metal-free and a solvent-free synthesis of thio-amides and amides: An
 efficient Friedel-Crafts arylation of isothiocyanates and isocyanates
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA12944J
_journal_year                    2014
_chemical_formula_moiety         'C14 H13 N O2 S'
_chemical_formula_sum            'C14 H13 N O2 S'
_chemical_formula_weight         259.31
_chemical_name_systematic        4-hydroxy-3-methoxy-N-phenylbenzothioamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-08-06
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.827(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7799(16)
_cell_length_b                   12.8970(16)
_cell_length_c                   7.5173(9)
_cell_measurement_reflns_used    3890
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.35
_cell_measurement_theta_min      2.26
_cell_volume                     1220.8(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7068
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.659
_diffrn_reflns_theta_min         2.260
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethylacetate:pet ether'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1080 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2641
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0354
_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)+(0.0459P)²+0.1112P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0866
_reflns_Friedel_coverage         0.857
_reflns_Friedel_fraction_full    0.934
_reflns_Friedel_fraction_max     0.858
_reflns_number_gt                2494
_reflns_number_total             2641
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ra12944j2.cif
_cod_data_source_block           new
_cod_database_code               7218647
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2013-2
_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_max   0.980
_shelx_estimated_absorpt_t_min   0.913
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, H11 of C11, H14 of C14, H9 of C9, H3 of C3, H8 of C8, H7
  of C7, H13 of C13, H12 of C12
 At 1.5 times of:
  All C(H,H,H) groups, H1 of C14
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C3(H3), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_olex2_submission_special_instructions 'No special instructions were received'
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
S1 S 0.49486(6) 0.33504(5) 0.77053(8) 0.0399(2) Uani 1 1 d .
O1 O 0.8524(2) 0.3755(2) 0.2242(3) 0.0562(6) Uani 1 1 d .
O2 O 0.88064(17) 0.34993(19) 0.5839(3) 0.0496(5) Uani 1 1 d .
N1 N 0.41690(17) 0.44857(18) 0.4838(3) 0.0342(5) Uani 1 1 d .
H1A H 0.4294 0.4810 0.3897 0.041 Uiso 1 1 calc R
C1 C 0.7667(2) 0.3742(2) 0.3098(4) 0.0387(6) Uani 1 1 d .
C2 C 0.7783(2) 0.3636(2) 0.4974(4) 0.0359(6) Uani 1 1 d .
C3 C 0.6906(2) 0.3677(2) 0.5803(3) 0.0338(5) Uani 1 1 d .
H3 H 0.6986 0.3610 0.7051 0.041 Uiso 1 1 calc R
C4 C 0.5895(2) 0.38163(18) 0.4782(3) 0.0303(5) Uani 1 1 d .
C5 C 0.4958(2) 0.39036(19) 0.5704(3) 0.0309(5) Uani 1 1 d .
C6 C 0.3137(2) 0.4631(2) 0.5297(3) 0.0326(5) Uani 1 1 d .
C7 C 0.2495(3) 0.3797(2) 0.5519(4) 0.0398(6) Uani 1 1 d .
H7 H 0.2745 0.3124 0.5447 0.048 Uiso 1 1 calc R
C8 C 0.1477(2) 0.3968(3) 0.5850(4) 0.0449(7) Uani 1 1 d .
H8 H 0.1042 0.3408 0.5997 0.054 Uiso 1 1 calc R
C9 C 0.1106(2) 0.4962(3) 0.5962(4) 0.0454(7) Uani 1 1 d .
H9 H 0.0422 0.5073 0.6188 0.054 Uiso 1 1 calc R
C10 C 0.8972(3) 0.3427(3) 0.7740(5) 0.0550(9) Uani 1 1 d .
H10A H 0.8704 0.4039 0.8232 0.082 Uiso 1 1 calc GR
H10B H 0.9718 0.3361 0.8193 0.082 Uiso 1 1 calc GR
H10C H 0.8607 0.2829 0.8088 0.082 Uiso 1 1 calc GR
C11 C 0.5793(2) 0.3885(2) 0.2910(3) 0.0367(6) Uani 1 1 d .
H11 H 0.5122 0.3959 0.2212 0.044 Uiso 1 1 calc R
C12 C 0.6671(2) 0.3846(2) 0.2087(4) 0.0406(7) Uani 1 1 d .
H12 H 0.6592 0.3889 0.0836 0.049 Uiso 1 1 calc R
C13 C 0.2763(2) 0.5631(2) 0.5381(4) 0.0397(6) Uani 1 1 d .
H13 H 0.3189 0.6192 0.5199 0.048 Uiso 1 1 calc R
C14 C 0.1747(3) 0.5794(3) 0.5739(4) 0.0461(7) Uani 1 1 d .
H14 H 0.1498 0.6466 0.5829 0.055 Uiso 1 1 calc R
H1 H 0.897(4) 0.355(4) 0.294(6) 0.069 Uiso 1 1 d 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
C1 O1 H1 104(4)
C2 O2 C10 117.1(2)
C5 N1 H1A 116.3
C5 N1 C6 127.3(2)
C6 N1 H1A 116.3
O1 C1 C2 121.4(3)
O1 C1 C12 118.8(3)
C12 C1 C2 119.8(2)
O2 C2 C1 114.8(2)
O2 C2 C3 125.2(3)
C3 C2 C1 119.9(2)
C2 C3 H3 119.8
C2 C3 C4 120.4(2)
C4 C3 H3 119.8
C3 C4 C5 119.7(2)
C11 C4 C3 118.8(2)
C11 C4 C5 121.5(2)
N1 C5 S1 124.1(2)
N1 C5 C4 114.6(2)
C4 C5 S1 121.28(19)
C7 C6 N1 121.3(2)
C7 C6 C13 120.3(3)
C13 C6 N1 118.3(2)
C6 C7 H7 120.2
C6 C7 C8 119.6(3)
C8 C7 H7 120.2
C7 C8 H8 119.8
C9 C8 C7 120.3(3)
C9 C8 H8 119.8
C8 C9 H9 120.0
C8 C9 C14 120.0(3)
C14 C9 H9 120.0
O2 C10 H10A 109.5
O2 C10 H10B 109.5
O2 C10 H10C 109.5
H10A C10 H10B 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C4 C11 H11 119.7
C12 C11 C4 120.6(2)
C12 C11 H11 119.7
C1 C12 C11 120.4(2)
C1 C12 H12 119.8
C11 C12 H12 119.8
C6 C13 H13 120.2
C6 C13 C14 119.6(3)
C14 C13 H13 120.2
C9 C14 C13 120.1(3)
C9 C14 H14 120.0
C13 C14 H14 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C5 1.667(3)
O1 C1 1.362(3)
O1 H1 0.75(5)
O2 C2 1.369(4)
O2 C10 1.412(4)
N1 H1A 0.8600
N1 C5 1.335(3)
N1 C6 1.431(3)
C1 C2 1.399(4)
C1 C12 1.372(4)
C2 C3 1.373(4)
C3 H3 0.9300
C3 C4 1.398(4)
C4 C5 1.487(4)
C4 C11 1.393(4)
C6 C7 1.380(4)
C6 C13 1.381(4)
C7 H7 0.9300
C7 C8 1.383(4)
C8 H8 0.9300
C8 C9 1.374(5)
C9 H9 0.9300
C9 C14 1.377(5)
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 H11 0.9300
C11 C12 1.373(4)
C12 H12 0.9300
C13 H13 0.9300
C13 C14 1.385(4)
C14 H14 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
C12 H12 S1 0.93 2.96 3.692(3) 136.9 1_554
O1 H1 O2 0.75(5) 2.22(5) 2.686(4) 121(5) .
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
O1 C1 C2 O2 -3.1(4)
O1 C1 C2 C3 176.8(2)
O1 C1 C12 C11 -176.9(3)
O2 C2 C3 C4 -179.8(3)
N1 C6 C7 C8 -175.9(2)
N1 C6 C13 C14 177.0(2)
C1 C2 C3 C4 0.4(4)
C2 C1 C12 C11 2.4(4)
C2 C3 C4 C5 -177.4(2)
C2 C3 C4 C11 1.7(4)
C3 C4 C5 S1 -27.2(3)
C3 C4 C5 N1 150.2(2)
C3 C4 C11 C12 -1.8(4)
C4 C11 C12 C1 -0.3(4)
C5 N1 C6 C7 -54.3(4)
C5 N1 C6 C13 130.5(3)
C5 C4 C11 C12 177.3(2)
C6 N1 C5 S1 -9.2(4)
C6 N1 C5 C4 173.5(2)
C6 C7 C8 C9 -0.2(4)
C6 C13 C14 C9 -1.7(4)
C7 C6 C13 C14 1.8(4)
C7 C8 C9 C14 0.2(5)
C8 C9 C14 C13 0.7(4)
C10 O2 C2 C1 177.8(3)
C10 O2 C2 C3 -2.1(4)
C11 C4 C5 S1 153.7(2)
C11 C4 C5 N1 -28.9(3)
C12 C1 C2 O2 177.7(3)
C12 C1 C2 C3 -2.5(4)
C13 C6 C7 C8 -0.8(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139199432
