Copper-catalyzed reaction of benzoxazinanones with sulfilimines: access to 2-ethynyl-benzoimidazoles <i>via</i> an abnormal skeletal rearrangement.
Zhang, Tao; Ni, Yifeng; Sun, Jiangtao; Organic & biomolecular chemistry 21 (2023) 4583–4586; doi:10.1039/d3ob00569k

data_7159350
_publ_section_title
;
 Copper-catalyzed reaction of benzoxazinanones with sulfilimines: access
 to 2-ethynyl-benzoimidazoles <i>via</i> an abnormal skeletal
 rearrangement.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; 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         'C21 H15 N3 O4 S'
_chemical_formula_sum            'C21 H15 N3 O4 S'
_chemical_formula_weight         405.42
_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
_audit_creation_date             2023-04-13
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;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2023-04-13 deposited with the CCDC.	2023-05-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.233(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1583(2)
_cell_length_b                   21.8770(3)
_cell_length_c                   10.2542(2)
_cell_measurement_reflns_used    10337
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      76.9680
_cell_measurement_theta_min      5.1280
_cell_volume                     1873.46(7)
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      301(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12222
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.261
_diffrn_reflns_theta_min         5.144
_exptl_absorpt_coefficient_mu    1.837
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       Block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0108(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0380
_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/[\s^2^(Fo^2^)+(0.0551P)^2^+0.4516P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1060
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3517
_reflns_number_total             3785
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00569k2.cif
_cod_data_source_block           zt-20230413_auto
_cod_depositor_comments
'Adding full bibliography for 7159349--7159350.cif.'
_cod_database_code               7159350
_shelx_shelxl_version_number     2017/1
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C2(H2)
1.b Aromatic/amide H refined with riding coordinates:
 C22(H22), C15(H15), C25(H25), C23(H23), C26(H26), C8(H8), C11(H11), C5(H5),
 C13(H13), C14(H14), C12(H12), C7(H7), C6(H6)
1.c :
 C20(H20)
;
_shelx_res_checksum              88588
_olex2_submission_special_instructions 'No special instructions were received'