Cascade Aryne Insertion/Vinylogous Aldol Reaction of Vinyl-substituted β-Keto/enol Carbonyls
Krishna Chaitanya, Nandikolla; Sambasiva Rao, Y. N.; Choutipalli, Venkata Surya Kumar; Mainkar, Prathama S.; Subramanian, Venkatesan; Chandrasekhar, Srivari; Chemical Communications  (2022) –; doi:10.1039/D1CC06810E

data_7129688
_publ_section_title
;
 Cascade Aryne Insertion/Vinylogous Aldol Reaction of Vinyl-substituted
 \b-Keto/enol Carbonyls
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06810E
_journal_year                    2022
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C21 H24 O3'
_chemical_formula_sum            'C21 H24 O3'
_chemical_formula_weight         324.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-12-29 deposited with the CCDC.	2022-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.723(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.549(3)
_cell_length_b                   12.882(5)
_cell_length_c                   10.906(5)
_cell_measurement_reflns_used    9297
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      56.73
_cell_measurement_theta_min      2.56
_cell_volume                     917.0(7)
_computing_cell_refinement       '<i>SAINT</i> (Bruker, 2016)'
_computing_data_collection       '<i>APEX3</i> (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  '<i>SHELXL2014</i> (Sheldrick, 2015)'
_computing_structure_solution    '<i>SHELXT</i> (Sheldrick, 2015)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            33298
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.541
_diffrn_reflns_theta_min         2.452
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1545 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         5572
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0518
_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^)+(0.0719P)^2^+0.0917P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1401
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                4019
_reflns_number_total             5572
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06810e2.cif
_cod_data_source_block           KA845_0m
_cod_original_cell_volume        916.9(7)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7129688
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.979
_shelx_estimated_absorpt_t_max   0.986
_shelx_res_checksum              92049