Photo-induced spirocyclization of biaryl ynones with ammonium thiocyanate: access to thiocyanate-featured spiro[5,5]trienones
Chen, Shiliu; Yan, Qinqin; Fan, Jie; Guo, Changyou; Li, Lijun; Liu, Zhong-Quan; Li, Zejiang; Green Chemistry 25 (2023) 153–160; doi:10.1039/D2GC03710F

data_7245973
_publ_section_title
;
 Photo-induced spirocyclization of biaryl ynones with ammonium
 thiocyanate: access to thiocyanate-featured spiro[5,5]trienones
;
_journal_issue                   1
_journal_name_full               'Green Chemistry'
_journal_page_first              153
_journal_page_last               160
_journal_paper_doi               10.1039/D2GC03710F
_journal_volume                  25
_journal_year                    2023
_chemical_formula_sum            'C22 H13 N O2 S'
_chemical_formula_weight         355.39
_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-2018/3
_audit_update_record
;
2022-09-30 deposited with the CCDC.	2022-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7823(9)
_cell_length_b                   17.2564(12)
_cell_length_c                   8.5563(5)
_cell_measurement_reflns_used    7385
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.75
_cell_measurement_theta_min      2.36
_cell_volume                     1739.7(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            19380
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.782
_diffrn_reflns_theta_min         2.093
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6880
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 1261 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3566
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0339
_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^)+(0.0229P)^2^+0.3890P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0788
_reflns_Friedel_coverage         0.799
_reflns_Friedel_fraction_full    0.929
_reflns_Friedel_fraction_max     0.916
_reflns_number_gt                3159
_reflns_number_total             3566
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2gc03710f2.cif
_cod_data_source_block           T9
_cod_depositor_comments          'Adding full bibliography for 7245973.cif.'
_cod_database_code               7245973
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.915
_shelx_estimated_absorpt_t_max   0.957
_shelx_res_checksum              30408