#------------------------------------------------------------------------------
#$Date: 2023-07-05 13:54:20 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284966 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/93/7159349.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_7159349
loop_
_publ_author_name
'Zhang, Tao'
'Ni, Yifeng'
'Sun, Jiangtao'
_publ_section_title
;
 Copper-catalyzed reaction of benzoxazinanones with sulfilimines: access
 to 2-ethynyl-benzoimidazoles via an abnormal skeletal
 rearrangement.
;
_journal_issue                   22
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4583
_journal_page_last               4586
_journal_paper_doi               10.1039/d3ob00569k
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C22 H18 N2 O2 S'
_chemical_formula_sum            'C22 H18 N2 O2 S'
_chemical_formula_weight         374.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-05
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-03-28 deposited with the CCDC.	2023-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.0440(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1365(2)
_cell_length_b                   21.8460(4)
_cell_length_c                   10.2421(2)
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    213.00
_cell_measurement_theta_max      54.974
_cell_measurement_theta_min      4.688
_cell_volume                     1836.70(7)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      213.00
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19091
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.949
_diffrn_reflns_theta_min         4.687
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.125
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1620 before and 0.0603 after correction.
The Ratio of minimum to maximum transmission is 0.7893.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0351
_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)+(0.0464P)²+0.6011P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0948
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3155
_reflns_number_total             3476
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00569k2.cif
_cod_data_source_block           220705sjt_0m
_cod_depositor_comments
'Adding full bibliography for 7159349--7159350.cif.'
_cod_database_code               7159349
_shelx_shelxl_version_number     2018/3
_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   0.946
_shelx_estimated_absorpt_t_min   0.925
_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 Ternary CH refined with riding coordinates:
 C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
2.d :
 C3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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
S1 S 0.78822(4) 0.55601(2) 0.63521(4) 0.03192(12) Uani 1 1 d . . . . .
O1 O 0.67940(14) 0.51004(5) 0.64002(12) 0.0413(3) Uani 1 1 d . . . . .
O2 O 0.94636(13) 0.56289(5) 0.75283(12) 0.0444(3) Uani 1 1 d . . . . .
N1 N 0.69438(14) 0.62332(5) 0.62666(12) 0.0290(3) Uani 1 1 d . . . . .
N2 N 0.54991(14) 0.67054(5) 0.40022(12) 0.0305(3) Uani 1 1 d . . . . .
C1 C 0.52842(16) 0.62904(6) 0.50363(14) 0.0284(3) Uani 1 1 d . . . . .
H1 H 0.488554 0.588610 0.458273 0.034 Uiso 1 1 calc R U . . .
C2 C 0.41568(18) 0.65557(7) 0.55598(16) 0.0355(3) Uani 1 1 d . . . . .
C3 C 0.3223(2) 0.67832(9) 0.5921(2) 0.0543(5) Uani 1 1 d . . . . .
H3 H 0.247865 0.696463 0.620971 0.065 Uiso 1 1 calc R U . . .
C4 C 0.47089(16) 0.65895(6) 0.24989(14) 0.0275(3) Uani 1 1 d . . . . .
C5 C 0.54050(18) 0.67434(7) 0.15739(15) 0.0339(3) Uani 1 1 d . . . . .
H5 H 0.641978 0.694231 0.194160 0.041 Uiso 1 1 calc R U . . .
C6 C 0.4594(2) 0.66017(8) 0.01135(16) 0.0409(4) Uani 1 1 d . . . . .
H6 H 0.506161 0.671015 -0.050865 0.049 Uiso 1 1 calc R U . . .
C7 C 0.3111(2) 0.63039(8) -0.04499(17) 0.0424(4) Uani 1 1 d . . . . .
H7 H 0.257670 0.620633 -0.144383 0.051 Uiso 1 1 calc R U . . .
C8 C 0.24233(19) 0.61517(7) 0.04653(17) 0.0393(4) Uani 1 1 d . . . . .
H8 H 0.141710 0.594656 0.009251 0.047 Uiso 1 1 calc R U . . .
C9 C 0.31988(17) 0.62977(7) 0.19251(16) 0.0333(3) Uani 1 1 d . . . . .
H9 H 0.270600 0.619990 0.253384 0.040 Uiso 1 1 calc R U . . .
C10 C 0.69432(17) 0.70314(6) 0.47724(15) 0.0285(3) Uani 1 1 d . . . . .
C11 C 0.78073(16) 0.67660(6) 0.61358(14) 0.0284(3) Uani 1 1 d . . . . .
C12 C 0.92632(18) 0.69996(7) 0.71477(16) 0.0360(3) Uani 1 1 d . . . . .
H12 H 0.983193 0.681252 0.805994 0.043 Uiso 1 1 calc R U . . .
C13 C 0.9864(2) 0.75213(8) 0.67749(18) 0.0430(4) Uani 1 1 d . . . . .
H13 H 1.085825 0.769099 0.744035 0.052 Uiso 1 1 calc R U . . .
C14 C 0.9012(2) 0.77912(7) 0.54362(19) 0.0434(4) Uani 1 1 d . . . . .
H14 H 0.943792 0.814556 0.521022 0.052 Uiso 1 1 calc R U . . .
C15 C 0.7536(2) 0.75562(7) 0.44045(17) 0.0368(3) Uani 1 1 d . . . . .
H15 H 0.696582 0.774566 0.349548 0.044 Uiso 1 1 calc R U . . .
C16 C 0.80288(18) 0.54990(6) 0.47068(16) 0.0312(3) Uani 1 1 d . . . . .
C17 C 0.92772(19) 0.58010(7) 0.45404(19) 0.0396(4) Uani 1 1 d . . . . .
H17 H 1.010088 0.600461 0.532981 0.048 Uiso 1 1 calc R U . . .
C18 C 0.9285(2) 0.57962(7) 0.3196(2) 0.0449(4) Uani 1 1 d . . . . .
H18 H 1.011950 0.600324 0.307623 0.054 Uiso 1 1 calc R U . . .
C19 C 0.8095(2) 0.54941(7) 0.20190(19) 0.0414(4) Uani 1 1 d . . . . .
C20 C 0.6880(2) 0.51879(7) 0.22213(18) 0.0410(4) Uani 1 1 d . . . . .
H20 H 0.607215 0.497605 0.143678 0.049 Uiso 1 1 calc R U . . .
C21 C 0.68308(19) 0.51875(7) 0.35507(16) 0.0355(3) Uani 1 1 d . . . . .
H21 H 0.599767 0.497903 0.367013 0.043 Uiso 1 1 calc R U . . .
C22 C 0.8100(3) 0.55021(9) 0.0551(2) 0.0594(5) Uani 1 1 d . . . . .
H22A H 0.749025 0.515380 -0.001335 0.089 Uiso 1 1 calc R U . . .
H22B H 0.921368 0.547989 0.067383 0.089 Uiso 1 1 calc R U . . .
H22C H 0.760031 0.587765 0.004780 0.089 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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 '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 S1 N1 105.62(6) . . ?
O1 S1 C16 109.12(7) . . ?
O2 S1 O1 120.48(7) . . ?
O2 S1 N1 104.81(6) . . ?
O2 S1 C16 110.09(7) . . ?
N1 S1 C16 105.56(6) . . ?
C1 N1 S1 114.98(9) . . ?
C11 N1 S1 114.95(9) . . ?
C11 N1 C1 104.37(10) . . ?
C4 N2 C1 120.68(11) . . ?
C10 N2 C1 107.38(11) . . ?
C10 N2 C4 127.77(11) . . ?
N1 C1 H1 110.5 . . ?
N2 C1 N1 104.61(10) . . ?
N2 C1 H1 110.5 . . ?
N2 C1 C2 110.81(11) . . ?
C2 C1 N1 109.85(11) . . ?
C2 C1 H1 110.5 . . ?
C3 C2 C1 176.96(18) . . ?
C2 C3 H3 180.0 . . ?
C5 C4 N2 122.15(13) . . ?
C9 C4 N2 118.75(12) . . ?
C9 C4 C5 119.08(13) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.59(14) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.29(14) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 120.5 . . ?
C8 C7 C6 119.08(14) . . ?
C8 C7 H7 120.5 . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.66(15) . . ?
C9 C8 H8 119.7 . . ?
C4 C9 H9 119.9 . . ?
C8 C9 C4 120.28(14) . . ?
C8 C9 H9 119.9 . . ?
C11 C10 N2 109.42(12) . . ?
C15 C10 N2 130.61(13) . . ?
C15 C10 C11 119.90(13) . . ?
C10 C11 N1 109.63(11) . . ?
C12 C11 N1 127.99(13) . . ?
C12 C11 C10 122.38(14) . . ?
C11 C12 H12 121.1 . . ?
C11 C12 C13 117.72(15) . . ?
C13 C12 H12 121.1 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.40(15) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 118.9 . . ?
C13 C14 C15 122.17(15) . . ?
C15 C14 H14 118.9 . . ?
C10 C15 C14 117.42(15) . . ?
C10 C15 H15 121.3 . . ?
C14 C15 H15 121.3 . . ?
C17 C16 S1 119.62(12) . . ?
C21 C16 S1 119.54(11) . . ?
C21 C16 C17 120.66(14) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 C16 118.83(15) . . ?
C18 C17 H17 120.6 . . ?
C17 C18 H18 119.1 . . ?
C17 C18 C19 121.73(15) . . ?
C19 C18 H18 119.1 . . ?
C18 C19 C20 118.25(15) . . ?
C18 C19 C22 121.20(16) . . ?
C20 C19 C22 120.55(16) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 C19 121.44(15) . . ?
C21 C20 H20 119.3 . . ?
C16 C21 H21 120.5 . . ?
C20 C21 C16 119.07(14) . . ?
C20 C21 H21 120.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
S1 O1 1.4292(11) . ?
S1 O2 1.4259(11) . ?
S1 N1 1.6850(12) . ?
S1 C16 1.7531(15) . ?
N1 C1 1.4916(17) . ?
N1 C11 1.4449(17) . ?
N2 C1 1.4714(17) . ?
N2 C4 1.4071(17) . ?
N2 C10 1.3986(17) . ?
C1 H1 0.9900 . ?
C1 C2 1.473(2) . ?
C2 C3 1.179(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.394(2) . ?
C4 C9 1.394(2) . ?
C5 H5 0.9400 . ?
C5 C6 1.382(2) . ?
C6 H6 0.9400 . ?
C6 C7 1.381(2) . ?
C7 H7 0.9400 . ?
C7 C8 1.379(2) . ?
C8 H8 0.9400 . ?
C8 C9 1.382(2) . ?
C9 H9 0.9400 . ?
C10 C11 1.393(2) . ?
C10 C15 1.389(2) . ?
C11 C12 1.3760(19) . ?
C12 H12 0.9400 . ?
C12 C13 1.389(2) . ?
C13 H13 0.9400 . ?
C13 C14 1.377(2) . ?
C14 H14 0.9400 . ?
C14 C15 1.395(2) . ?
C15 H15 0.9400 . ?
C16 C17 1.391(2) . ?
C16 C21 1.388(2) . ?
C17 H17 0.9400 . ?
C17 C18 1.380(2) . ?
C18 H18 0.9400 . ?
C18 C19 1.386(2) . ?
C19 C20 1.387(2) . ?
C19 C22 1.506(2) . ?
C20 H20 0.9400 . ?
C20 C21 1.382(2) . ?
C21 H21 0.9400 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
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
S1 N1 C1 N2 -106.08(10) . . . . ?
S1 N1 C1 C2 134.94(10) . . . . ?
S1 N1 C11 C10 112.37(11) . . . . ?
S1 N1 C11 C12 -67.22(16) . . . . ?
S1 C16 C17 C18 -173.90(12) . . . . ?
S1 C16 C21 C20 174.34(12) . . . . ?
O1 S1 N1 C1 -55.83(10) . . . . ?
O1 S1 N1 C11 -177.07(9) . . . . ?
O1 S1 C16 C17 -165.62(12) . . . . ?
O1 S1 C16 C21 19.08(14) . . . . ?
O2 S1 N1 C1 175.95(9) . . . . ?
O2 S1 N1 C11 54.71(11) . . . . ?
O2 S1 C16 C17 -31.32(14) . . . . ?
O2 S1 C16 C21 153.38(12) . . . . ?
N1 S1 C16 C17 81.28(13) . . . . ?
N1 S1 C16 C21 -94.02(13) . . . . ?
N1 C11 C12 C13 179.94(13) . . . . ?
N2 C4 C5 C6 178.04(13) . . . . ?
N2 C4 C9 C8 -177.03(13) . . . . ?
N2 C10 C11 N1 1.99(15) . . . . ?
N2 C10 C11 C12 -178.40(12) . . . . ?
N2 C10 C15 C14 177.61(14) . . . . ?
C1 N1 C11 C10 -14.50(14) . . . . ?
C1 N1 C11 C12 165.91(13) . . . . ?
C1 N2 C4 C5 -147.04(13) . . . . ?
C1 N2 C4 C9 31.36(19) . . . . ?
C1 N2 C10 C11 11.75(15) . . . . ?
C1 N2 C10 C15 -165.29(14) . . . . ?
C4 N2 C1 N1 138.52(12) . . . . ?
C4 N2 C1 C2 -103.16(14) . . . . ?
C4 N2 C10 C11 -145.03(13) . . . . ?
C4 N2 C10 C15 37.9(2) . . . . ?
C4 C5 C6 C7 -0.7(2) . . . . ?
C5 C4 C9 C8 1.4(2) . . . . ?
C5 C6 C7 C8 0.7(2) . . . . ?
C6 C7 C8 C9 0.4(2) . . . . ?
C7 C8 C9 C4 -1.5(2) . . . . ?
C9 C4 C5 C6 -0.3(2) . . . . ?
C10 N2 C1 N1 -20.23(13) . . . . ?
C10 N2 C1 C2 98.09(13) . . . . ?
C10 N2 C4 C5 7.0(2) . . . . ?
C10 N2 C4 C9 -174.60(13) . . . . ?
C10 C11 C12 C13 0.4(2) . . . . ?
C11 N1 C1 N2 20.76(12) . . . . ?
C11 N1 C1 C2 -98.21(12) . . . . ?
C11 C10 C15 C14 0.8(2) . . . . ?
C11 C12 C13 C14 0.3(2) . . . . ?
C12 C13 C14 C15 -0.4(2) . . . . ?
C13 C14 C15 C10 -0.1(2) . . . . ?
C15 C10 C11 N1 179.39(12) . . . . ?
C15 C10 C11 C12 -1.0(2) . . . . ?
C16 S1 N1 C1 59.70(10) . . . . ?
C16 S1 N1 C11 -61.54(11) . . . . ?
C16 C17 C18 C19 -0.7(2) . . . . ?
C17 C16 C21 C20 -0.9(2) . . . . ?
C17 C18 C19 C20 -0.4(2) . . . . ?
C17 C18 C19 C22 178.88(16) . . . . ?
C18 C19 C20 C21 0.9(2) . . . . ?
C19 C20 C21 C16 -0.2(2) . . . . ?
C21 C16 C17 C18 1.3(2) . . . . ?
C22 C19 C20 C21 -178.43(15) . . . . ?
