Electronically-controlled diastereoselective synthesis of spirocycles <i>via</i> [4 + 2] cycloaddition of 2-arylidene-1-indenones with benzyne.
Ray, Subhasish; Yadav, Anup Kumar; Singh, Saurabh; Ansari, Monish Arbaz; Singh, Maya Shankar; Organic & biomolecular chemistry 21 (2023) 4195–4199; doi:10.1039/d3ob00417a

data_7159329
_publ_section_title
;
 Electronically-controlled diastereoselective synthesis of spirocycles
 <i>via</i> [4 + 2] cycloaddition of 2-arylidene-1-indenones with benzyne.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4195
_journal_page_last               4199
_journal_paper_doi               10.1039/d3ob00417a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C23 H17 F O2'
_chemical_formula_sum            'C23 H16 F O2'
_chemical_formula_weight         343.36
_chemical_name_systematic        Ray
_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
_audit_creation_date             2023-01-21
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-01-21 deposited with the CCDC.	2023-04-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.4412(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.03311(10)
_cell_length_b                   24.9979(3)
_cell_length_c                   8.69995(10)
_cell_measurement_reflns_used    12111
_cell_measurement_temperature    293
_cell_measurement_theta_max      33.3070
_cell_measurement_theta_min      3.2290
_cell_volume                     1723.38(4)
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293.00
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type
'CrysAlisPro 1.171.42.63a (Rigaku Oxford Diffraction, 2022)'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16410
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.095
_diffrn_reflns_theta_min         3.536
_exptl_absorpt_coefficient_mu    0.739
_exptl_absorpt_correction_T_max  29.3
_exptl_absorpt_correction_T_min  2.3
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Abs
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       block
_exptl_crystal_F_000             716
_exptl_crystal_preparation       MeOH
_exptl_crystal_recrystallization_method MeOH
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3126
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0462
_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^)+(0.0702P)^2^+0.1825P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1221
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2758
_reflns_number_total             3126
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00417a3.cif
_cod_data_source_block           ov_ray-203_auto
_cod_depositor_comments
'Adding full bibliography for 7159329--7159330.cif.'
_cod_database_code               7159329
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.866
_shelx_estimated_absorpt_t_min   0.866
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C16(H16), C25(H25), C4(H4), C5(H5), C13(H13), C14(H14),
 C23(H23), C22(H22)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              37770
_olex2_submission_special_instructions 'No special instructions were received'