Copper(I)-catalyzed electrophilic thiocyanation/dearomatization/spirocyclization of benzofurans to synthesize benzannulated spiroketals.
He, Ying; Wang, Qing; Yin, Hongquan; Chen, Fu-Xue; Organic & biomolecular chemistry 21 (2023) 4216–4219; doi:10.1039/d3ob00438d

data_7159340
_publ_section_title
;
 Copper(I)-catalyzed electrophilic
 thiocyanation/dearomatization/spirocyclization of benzofurans to
 synthesize benzannulated spiroketals.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4216
_journal_page_last               4219
_journal_paper_doi               10.1039/d3ob00438d
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C13 H13 N O2 S'
_chemical_formula_weight         247.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2023-03-21 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.128(6)
_cell_length_b                   5.8764(19)
_cell_length_c                   26.359(9)
_cell_measurement_reflns_used    3451
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      16.92
_cell_measurement_theta_min      2.64
_cell_volume                     2498.2(15)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  ccd
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1676
_diffrn_reflns_av_unetI/netI     0.1445
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            29056
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         2.526
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details
;
 Flack x determined using 699 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.48(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4260
_refine_ls_number_restraints     229
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.2397
_refine_ls_R_factor_gt           0.1322
_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/[\s^2^(Fo^2^)+(0.0137P)^2^+32.7393P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2315
_refine_ls_wR_factor_ref         0.2698
_reflns_Friedel_coverage         0.916
_reflns_Friedel_fraction_full    0.953
_reflns_Friedel_fraction_max     0.953
_reflns_number_gt                2207
_reflns_number_total             4260
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00438d2.cif
_cod_data_source_block           1_a
_cod_depositor_comments          'Adding full bibliography for 7159340.cif.'
_cod_original_cell_volume        2498.3(15)
_cod_database_code               7159340
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.952
_shelx_estimated_absorpt_t_max   0.952
_shelx_res_checksum              53867
_shelx_hkl_checksum              93715