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_7159330
_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         'C29 H22 O'
_chemical_formula_sum            'C29 H22 O'
_chemical_formula_weight         386.497
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-09-21
_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                 94.2755(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.38262(19)
_cell_length_b                   11.76838(19)
_cell_length_c                   14.2059(2)
_cell_measurement_reflns_used    1283
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.3
_cell_volume                     2064.37(5)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.9863
_diffrn_measured_fraction_theta_max 0.9793
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.9863
_diffrn_reflns_Laue_measured_fraction_max 0.9793
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11591
_diffrn_reflns_point_group_measured_fraction_full 0.9863
_diffrn_reflns_point_group_measured_fraction_max 0.9793
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         68.13
_diffrn_reflns_theta_min         4.92
_exptl_absorpt_coefficient_mu    0.567
_exptl_absorpt_correction_T_max  28.2
_exptl_absorpt_correction_T_min  2.3
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       block
_exptl_crystal_F_000             818.437
_exptl_crystal_preparation       'Ethanol evaporation'
_exptl_crystal_recrystallization_method Ethanol
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.1887
_refine_diff_density_min         -0.1656
_refine_diff_density_rms         0.0310
_refine_ls_d_res_high            0.8307
_refine_ls_d_res_low             8.9826
_refine_ls_goodness_of_fit_ref   1.0321
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    38
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3685
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0321
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0506P)^2^+0.2257P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0970
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -14
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              -10
_reflns_number_gt                3092
_reflns_number_total             3685
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3ob00417a3.cif
_cod_data_source_block           RAY142_auto
_cod_depositor_comments
'Adding full bibliography for 7159329--7159330.cif.'
_cod_original_cell_volume        2064.37(6)
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               7159330
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C23(H23), C3(H3), C16(H16), C26(H26), C30(H30), C6(H6), C20(H20), C13(H13),
 C21(H21), C5(H5), C4(H4), C15(H15), C29(H29), C27(H27), C14(H14), C28(H28)
2.c Idealised Me refined as rotating group:
 C24(H24a,H24b,H24c)
;
_olex2_date_sample_submission    2022-09-15
_olex2_submission_special_instructions 'No special instructions were received'