Single-Flask Multicomponent Synthesis of Highly Substituted α-Pyrones via a Sequential Enolate Arylation and Alkenylation Strategy.
Grigalunas, Michael; Wiest, Olaf; Helquist, Paul; Organic letters 18 (2016) 5724–5727; doi:10.1021/acs.orglett.6b02969

data_1544342
_publ_section_title
;
 Single-Flask Multicomponent Synthesis of Highly Substituted \a-Pyrones
 via a Sequential Enolate Arylation and Alkenylation Strategy.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5724
_journal_page_last               5727
_journal_paper_doi               10.1021/acs.orglett.6b02969
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C36 H22 F10 O5, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C38 H26 F10 O6'
_chemical_formula_weight         768.58
_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_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     vecmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 95.407(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.1826(9)
_cell_length_b                   25.666(3)
_cell_length_c                   31.715(4)
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.28
_cell_measurement_theta_min      2.46
_cell_volume                     6631.0(14)
_computing_cell_refinement       'Bruker SAINT (Bruker, 2015)'
_computing_data_collection       'Bruker APEX-3 (Bruker, 2015)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2015)'
_computing_molecular_graphics    'Bruker XP (Bruker, 2015)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            113081
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.378
_diffrn_reflns_theta_min         1.022
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9362
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_description       rod
_exptl_crystal_F_000             3136
_exptl_crystal_size_max          0.237
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.078
_refine_diff_density_max         1.606
_refine_diff_density_min         -0.830
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     998
_refine_ls_number_reflns         13556
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0545
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0652P)^2^+9.5679P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1366
_refine_ls_wR_factor_ref         0.1502
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10197
_reflns_number_total             13556
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02969_si_001.cif
_cod_data_source_block           nd1609
_cod_depositor_comments
;
Adding full bibliography for 1544342--1544343.cif.

2019-07-12
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        6631.0(13)
_cod_original_formula_moiety     '2(C36 H22 F10 O5), C4 H8 O2'
_cod_original_formula_sum        'C76 H52 F20 O12'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     1537.17
_cod_database_code               1544342
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.989
_diffrn_source_monochromator     'Bruker TRIUMPH curved-graphite'
_shelx_res_checksum              25699
_shelx_hkl_checksum              32511