Aryl iodine-catalysed divergent synthesis of isobenzofuranones and isocoumarins via oxidative 1,2-aryl migration/elimination
He, Jiaxin; Zhang, Jingran; Li, Xuemin; Shi, Haofeng; Du, Yunfei; Chemical Communications  (2022) –; doi:10.1039/D2CC03101A

data_7130387
_publ_section_title
;
 Aryl iodine-catalysed divergent synthesis of isobenzofuranones and
 isocoumarins via oxidative 1,2-aryl migration/elimination
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03101A
_journal_year                    2022
_chemical_formula_moiety         'C20 H29 I O5 S'
_chemical_formula_sum            'C20 H29 I O5 S'
_chemical_formula_weight         508.39
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-06-30
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-06-30 deposited with the CCDC.	2022-07-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.03(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.715(3)
_cell_length_b                   7.0850(14)
_cell_length_c                   21.523(4)
_cell_measurement_reflns_used    17283
_cell_measurement_temperature    298
_cell_measurement_theta_max      52.742
_cell_measurement_theta_min      6.082
_cell_volume                     2145.5(8)
_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      298
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'RIGAKU R-AXIS4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0720
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            17283
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.041
_exptl_absorpt_coefficient_mu    1.617
_exptl_absorpt_correction_T_max  0.922
_exptl_absorpt_correction_T_min  0.792
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_description       plate
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.545
_refine_diff_density_min         -0.855
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4317
_refine_ls_number_restraints     362
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0512
_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^)+(0.0581P)^2^+4.2913P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1382
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3337
_reflns_number_total             4317
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03101a2.cif
_cod_data_source_block           a
_cod_database_code               7130387
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.924
_shelx_estimated_absorpt_t_min   0.793
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H18-O18
 0.9 with sigma of 0.02
 C20-C17 \\sim C20-C17A
 with sigma of 0.02
 C21-C17 \\sim C21A-C17A
 with sigma of 0.02
 C23-C9 \\sim C23A-C9A
 with sigma of 0.04
 C21-O25 \\sim C21A-O25A
 with sigma of 0.02
 C21-C9 \\sim C21A-C9A
 with sigma of 0.02
 C17-C9 \\sim C17A-C9A
 with sigma of 0.04
 C19-C23 \\sim C19A-C23A
 with sigma of 0.02
 O25-C9 \\sim O25A-C9A
 with sigma of 0.04
 C19-C9 \\sim C19A-C9A
 with sigma of 0.02
 C17-O25 \\sim C17A-O25A
 with sigma of 0.04
 C19-C27 \\sim C19A-C27A
 with sigma of 0.02
 C20-C21 \\sim C20-C21A
 with sigma of 0.04
 C19-C21 \\sim C19A-C21A
 with sigma of 0.04
 C21-C5 \\sim C21A-C5A
 with sigma of 0.04
 C21-C23 \\sim C21A-C23A
 with sigma of 0.04
 C17-C5 \\sim C17A-C5A
 with sigma of 0.02
 C17-C23 \\sim C17A-C23A
 with sigma of 0.02
 C17-C3 \\sim C17A-C3A
 with sigma of 0.04
 C11-C23 \\sim C11A-C23A
 with sigma of 0.02
 C5-C23 \\sim C5A-C23A
 with sigma of 0.04
 C5-C27 \\sim C5A-C27A
 with sigma of 0.02
 C23-C3 \\sim C23A-C3A
 with sigma of 0.02
 C17-C11 \\sim C17A-C11A
 with sigma of 0.04
 C17-C27 \\sim C17A-C27A
 with sigma of 0.04
 C11-C3 \\sim C11A-C3A
 with sigma of 0.04
 C20-C5 \\sim C20-C5A
 with sigma of 0.04
 C23-C27 \\sim C23A-C27A
 with sigma of 0.04
 C20-C23 \\sim C20-C23A
 with sigma of 0.04
 C19-C17 \\sim C19A-C17A
 with sigma of 0.04
 C19-C11 \\sim C19A-C11A
 with sigma of 0.04
 C19-C5 \\sim C19A-C5A
 with sigma of 0.04
 C19-C3 \\sim C19A-C3A
 with sigma of 0.04
 C9-C27 \\sim C9A-C27A
 with sigma of 0.04
3. Rigid bond restraints
 C21, O25
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C21 \\sim O25: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.02 within 2A
5. Rigid body (RIGU) restrains
 C19, C21, C17, C11, C5, C23, C3, O25, C9, C27
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C19A, C21A, C17A, C11A, C5A, C23A, C3A, O25A, C9A, C27A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(H20C)=Sof(H20D)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=Sof(C11A)=
 Sof(H11D)=Sof(H11E)=Sof(H11F)=Sof(C17A)=Sof(O25A)=Sof(C21A)=Sof(C9A)=Sof(H9AA)=
 Sof(H9AB)=Sof(C19A)=Sof(H19A)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(C27A)=Sof(H27C)=
 Sof(H27D)=Sof(C23A)=1-FVAR(1)
 Sof(H20A)=Sof(H20B)=Sof(C19)=Sof(H19)=Sof(C21)=Sof(C17)=Sof(C11)=Sof(H11A)=
 Sof(H11B)=Sof(H11C)=Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(C23)=Sof(C3)=Sof(H3A)=
 Sof(H3B)=Sof(H3C)=Sof(O25)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(C27)=Sof(H27A)=
 Sof(H27B)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C19(H19), C19A(H19A)
7.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C20(H20C,H20D), C5(H5A,H5B), C9(H9A,H9B), C27(H27A,H27B),
 C9A(H9AA,H9AB), C5A(H5AA,H5AB), C27A(H27C,H27D)
7.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C24(H24), C16(H16)
7.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C2(H2A,H2B,H2C), C11(H11A,H11B,
 H11C), C3(H3A,H3B,H3C), C3A(H3AA,H3AB,H3AC), C11A(H11D,H11E,H11F)
;
_shelx_res_checksum              37335
_shelx_hkl_checksum              97341
_olex2_submission_special_instructions 'No special instructions were received'