Regiospecific formal [3 + 2] annulation of tert-propargyl alcohols with acyclic 1,3-diketones via the cycloisomerization of homoallenyl ketones.
Yaragorla, Srinivasarao; Rajesh, P.; Organic & biomolecular chemistry 17 (2019) 1924–1928; doi:10.1039/c8ob02158a

data_7156464
_publ_section_title
;
 Regiospecific formal [3 + 2] annulation of tert-propargyl alcohols with
 acyclic 1,3-diketones via the cycloisomerization of homoallenyl ketones.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1924
_journal_page_last               1928
_journal_paper_doi               10.1039/c8ob02158a
_journal_volume                  17
_journal_year                    2019
_chemical_formula_sum            'C27 H23 O3'
_chemical_formula_weight         395.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-06-25 deposited with the CCDC.
2018-09-26 downloaded from the CCDC.
;
_cell_angle_alpha                87.971(4)
_cell_angle_beta                 75.802(4)
_cell_angle_gamma                85.937(4)
_cell_formula_units_Z            2
_cell_length_a                   9.8049(9)
_cell_length_b                   9.8109(10)
_cell_length_c                   11.3980(12)
_cell_measurement_reflns_used    9882
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      2.75
_cell_volume                     1060.08(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            48875
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.973
_diffrn_reflns_theta_min         2.466
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       plate
_exptl_crystal_F_000             418
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.677
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5052
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0603
_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^)+(0.0780P)^2^+0.4851P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1658
_refine_ls_wR_factor_ref         0.1761
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3935
_reflns_number_total             5052
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02158a2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7156464--7156465.cif.'
_cod_database_code               7156464
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              37038