#------------------------------------------------------------------------------
#$Date: 2022-02-22 04:10:16 +0200 (Tue, 22 Feb 2022) $
#$Revision: 273077 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/44/7244463.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_7244463
loop_
_publ_author_name
'Moussa, Ziad'
'Judeh, Zaher M. A.'
'Alzamly, Ahmed'
'Ahmed, Saleh A.'
'Tomah Al-Masri, Harbi'
'Al-Hindawi, Bassam'
'Rasool, Faisal'
'Saada, Sara'
_publ_section_title
;
 Iodine-DMSO mediated conversion of N-arylcyanothioformamides to
 N-arylcyanoformamides and the unexpected formation of
 2-cyanobenzothiazoles
;
_journal_issue                   10
_journal_name_full               'RSC Advances'
_journal_page_first              6133
_journal_page_last               6148
_journal_paper_doi               10.1039/D2RA00049K
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C10 H8 N2 O2 S'
_chemical_formula_sum            'C10 H8 N2 O2 S'
_chemical_formula_weight         220.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-12-28 deposited with the CCDC.	2022-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.509(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.9979(2)
_cell_length_b                   15.5449(11)
_cell_length_c                   15.9729(8)
_cell_measurement_reflns_used    3863
_cell_measurement_temperature    297.00(10)
_cell_measurement_theta_max      76.6170
_cell_measurement_theta_min      5.4810
_cell_volume                     992.63(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00 -25.00   0.50    1.39    --  -49.51 149.00  73.00  156
  2  ω    -84.00 -11.00   0.50    1.39    --  -49.51 123.00 -90.00  146
  3  ω   -120.00 -57.00   0.50    1.39    --  -49.51-149.00  26.00  126
  4  ω     47.00 109.00   0.50    1.39    --   49.51-149.00  26.00  124
  5  ω     33.00  93.00   0.50    1.39    --   49.51-123.00-170.00  120
  6  ω   -103.00 -25.00   0.50    5.54    --  -90.00 149.00  73.00  156
  7  ω   -161.00 -75.00   0.50    5.54    --  -90.00-123.00-170.00  172
  8  ω     33.00 110.00   0.50    5.54    --  104.80-123.00-170.00  154
  9  ω     47.00 129.00   0.50    5.54    --  104.80-149.00  26.00  164
 10  ω    122.00 158.00   0.50    5.54    --  104.80 149.00  73.00   72
 11  ω    -23.00  18.00   0.50    1.39    --  -49.51  19.00-150.00   82
 12  ω    -26.00  13.00   0.50    1.39    --  -49.51  19.00 120.00   78
 13  ω    -10.00  20.00   0.50    1.39    --  -49.51  19.00  60.00   60
 14  ω     -5.00  21.00   0.50    1.39    --   49.51 -19.00 120.00   52
 15  ω   -160.00-131.00   0.50    5.54    --  -90.00 -37.00-120.00   58
 16  ω   -160.00-131.00   0.50    5.54    --  -90.00 -37.00-180.00   58
 17  ω   -159.00-127.00   0.50    5.54    --  -90.00 -99.00 -30.00   64
 18  ω   -159.00-132.00   0.50    5.54    --  -90.00 -37.00 -90.00   54
 19  ω   -161.00-136.00   0.50    5.54    --  -90.00 -77.00  30.00   50
 20  ω   -160.00-133.00   0.50    5.54    --  -90.00 -37.00-150.00   54
 21  ω   -161.00-133.00   0.50    5.54    --  -90.00 -37.00 -60.00   56
 22  ω   -161.00-128.00   0.50    5.54    --  -90.00 -99.00 120.00   66
 23  ω     57.00 106.00   0.50    5.54    --  104.80 -99.00-120.00   98
 24  ω    115.00 175.00   0.50    5.54    --  104.80 125.00 -30.00  120
 25  ω     33.00  58.00   0.50    5.54    --  104.80 -57.00  60.00   50
 26  ω     38.00  63.00   0.50    5.54    --  104.80 -57.00 -30.00   50
 27  ω    137.00 162.00   0.50    5.54    --  104.80  57.00-180.00   50
 28  ω     38.00  63.00   0.50    5.54    --  104.80 -57.00 -90.00   50
 29  ω     37.00  65.00   0.50    5.54    --  104.80 -57.00-120.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0573435000
_diffrn_orient_matrix_UB_12      -0.0637842000
_diffrn_orient_matrix_UB_13      -0.0723861000
_diffrn_orient_matrix_UB_21      -0.0028702000
_diffrn_orient_matrix_UB_22      -0.0753605000
_diffrn_orient_matrix_UB_23      0.0625373000
_diffrn_orient_matrix_UB_31      -0.3810061000
_diffrn_orient_matrix_UB_32      -0.0090450000
_diffrn_orient_matrix_UB_33      -0.0121376000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7605
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.364
_diffrn_reflns_theta_min         5.540
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.752
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.742
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_description       needle
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.278
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1900
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0752P)²+0.1720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1349
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1491
_reflns_number_total             1900
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra00049k2.cif
_cod_data_source_block           exp_235_auto
_cod_database_code               7244463
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_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   0.932
_shelx_estimated_absorpt_t_min   0.515
_reflns_odcompleteness_completeness 97.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.558
_oxdiff_exptl_absorpt_empirical_full_min 0.531
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S5 S 0.36317(15) 0.31238(4) 0.73209(4) 0.0566(2) Uani 1 1 d . . . . .
O10 O 0.4994(4) 0.30854(11) 0.36912(10) 0.0585(5) Uani 1 1 d . . . . .
O12 O 0.7434(5) 0.18078(11) 0.44660(11) 0.0598(5) Uani 1 1 d . . . . .
N7 N 0.1504(5) 0.43523(14) 0.63390(13) 0.0528(5) Uani 1 1 d . . . . .
C8 C 0.2953(5) 0.37396(15) 0.58331(14) 0.0478(5) Uani 1 1 d . . . . .
C1 C 0.4629(6) 0.31278(15) 0.45339(15) 0.0484(5) Uani 1 1 d . . . . .
C4 C 0.4284(6) 0.30241(16) 0.62571(15) 0.0491(5) Uani 1 1 d . . . . .
C2 C 0.6012(5) 0.24057(16) 0.49738(15) 0.0490(6) Uani 1 1 d . . . . .
C3 C 0.5815(5) 0.23457(16) 0.58277(15) 0.0504(6) Uani 1 1 d . . . . .
H3 H 0.666899 0.187119 0.611260 0.061 Uiso 1 1 calc R U . . .
C9 C 0.3124(6) 0.37900(15) 0.49589(15) 0.0493(5) Uani 1 1 d . . . . .
H9 H 0.224027 0.426027 0.467291 0.059 Uiso 1 1 calc R U . . .
C6 C 0.1722(6) 0.41041(17) 0.71171(15) 0.0534(6) Uani 1 1 d . . . . .
N15 N -0.0474(8) 0.50529(19) 0.83161(16) 0.0830(8) Uani 1 1 d . . . . .
C14 C 0.0490(7) 0.46266(19) 0.77919(17) 0.0626(7) Uani 1 1 d . . . . .
C11 C 0.3420(7) 0.37457(19) 0.32058(16) 0.0599(6) Uani 1 1 d . . . . .
H11A H 0.385654 0.365125 0.262297 0.090 Uiso 1 1 calc R U . . .
H11B H 0.429463 0.429584 0.337074 0.090 Uiso 1 1 calc R U . . .
H11C H 0.105030 0.373344 0.329759 0.090 Uiso 1 1 calc R U . . .
C13 C 0.8818(7) 0.10591(18) 0.48554(18) 0.0605(7) Uani 1 1 d . . . . .
H13A H 0.988758 0.070987 0.444058 0.091 Uiso 1 1 calc R U . . .
H13B H 0.706379 0.073550 0.511485 0.091 Uiso 1 1 calc R U . . .
H13C H 1.043130 0.122873 0.527230 0.091 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 0 1 0.1353
-3 0 -1 0.1383
0 5 -1 0.0143
0 -5 1 0.0120
0 -1 -5 0.0234
0 1 5 0.0074
-2 7 -2 0.0960
2 -7 2 0.0960
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
C4 S5 C6 87.95(12) . . ?
C1 O10 C11 116.92(18) . . ?
C2 O12 C13 117.3(2) . . ?
C6 N7 C8 109.2(2) . . ?
N7 C8 C4 115.1(2) . . ?
N7 C8 C9 124.7(2) . . ?
C9 C8 C4 120.2(2) . . ?
O10 C1 C2 113.84(19) . . ?
O10 C1 C9 125.3(2) . . ?
C9 C1 C2 120.9(2) . . ?
C8 C4 S5 110.07(17) . . ?
C3 C4 S5 128.2(2) . . ?
C3 C4 C8 121.7(2) . . ?
O12 C2 C1 113.8(2) . . ?
O12 C2 C3 125.1(2) . . ?
C3 C2 C1 121.1(2) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 C4 117.7(2) . . ?
C2 C3 H3 121.1 . . ?
C8 C9 H9 120.8 . . ?
C1 C9 C8 118.4(2) . . ?
C1 C9 H9 120.8 . . ?
N7 C6 S5 117.69(18) . . ?
N7 C6 C14 121.8(2) . . ?
C14 C6 S5 120.5(2) . . ?
N15 C14 C6 178.7(3) . . ?
O10 C11 H11A 109.5 . . ?
O10 C11 H11B 109.5 . . ?
O10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O12 C13 H13A 109.5 . . ?
O12 C13 H13B 109.5 . . ?
O12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
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
S5 C4 1.728(2) . ?
S5 C6 1.734(3) . ?
O10 C1 1.357(3) . ?
O10 C11 1.429(3) . ?
O12 C2 1.361(3) . ?
O12 C13 1.429(3) . ?
N7 C8 1.380(3) . ?
N7 C6 1.303(3) . ?
C8 C4 1.405(3) . ?
C8 C9 1.401(3) . ?
C1 C2 1.433(3) . ?
C1 C9 1.375(3) . ?
C4 C3 1.402(3) . ?
C2 C3 1.370(3) . ?
C3 H3 0.9300 . ?
C9 H9 0.9300 . ?
C6 C14 1.440(4) . ?
N15 C14 1.138(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
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
_geom_torsion_publ_flag
S5 C4 C3 C2 179.20(18) . . . . ?
O10 C1 C2 O12 -0.1(3) . . . . ?
O10 C1 C2 C3 -179.2(2) . . . . ?
O10 C1 C9 C8 -179.8(2) . . . . ?
O12 C2 C3 C4 179.6(2) . . . . ?
N7 C8 C4 S5 0.8(3) . . . . ?
N7 C8 C4 C3 179.6(2) . . . . ?
N7 C8 C9 C1 -179.6(2) . . . . ?
C8 N7 C6 S5 -0.4(3) . . . . ?
C8 N7 C6 C14 178.4(2) . . . . ?
C8 C4 C3 C2 0.7(3) . . . . ?
C1 C2 C3 C4 -1.4(3) . . . . ?
C4 S5 C6 N7 0.7(2) . . . . ?
C4 S5 C6 C14 -178.1(2) . . . . ?
C4 C8 C9 C1 -0.3(3) . . . . ?
C2 C1 C9 C8 -0.4(3) . . . . ?
C9 C8 C4 S5 -178.58(18) . . . . ?
C9 C8 C4 C3 0.2(3) . . . . ?
C9 C1 C2 O12 -179.6(2) . . . . ?
C9 C1 C2 C3 1.3(4) . . . . ?
C6 S5 C4 C8 -0.81(18) . . . . ?
C6 S5 C4 C3 -179.4(2) . . . . ?
C6 N7 C8 C4 -0.3(3) . . . . ?
C6 N7 C8 C9 179.1(2) . . . . ?
C11 O10 C1 C2 174.7(2) . . . . ?
C11 O10 C1 C9 -5.9(3) . . . . ?
C13 O12 C2 C1 -178.9(2) . . . . ?
C13 O12 C2 C3 0.2(3) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.0001 -0.0162 1.0482 0.0972 0.0582 -1.1556
-3.0001 0.0162 -1.0482 -0.0972 -0.0582 1.1556
0.0002 5.0115 -1.0165 -0.2461 -0.4412 -0.0331
-0.0002 -5.0115 1.0165 0.2461 0.4412 0.0331
0.0030 -0.9943 -5.0135 0.4265 -0.2386 0.0687
-0.0030 0.9943 5.0135 -0.4265 0.2386 -0.0687
-1.9998 7.0268 -2.0551 -0.4141 -0.6523 0.7233
1.9998 -7.0268 2.0551 0.4141 0.6523 -0.7233
