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_1544343
_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         'C28 H25 O9, C H2 Cl2, 0.25(H2 O)'
_chemical_formula_sum            'C28 H26.5 Cl2 O9.25'
_chemical_formula_weight         581.89
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     vecmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 105.0980(10)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   27.9493(7)
_cell_length_b                   14.6228(4)
_cell_length_c                   26.5088(7)
_cell_measurement_reflns_used    9795
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      71.84
_cell_measurement_theta_min      3.45
_cell_volume                     10460.1(5)
_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 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            250239
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.039
_diffrn_reflns_theta_min         1.637
_diffrn_source                   'Incoatec micro-focus'
_exptl_absorpt_coefficient_mu    2.727
_exptl_absorpt_correction_T_max  0.8644
_exptl_absorpt_correction_T_min  0.6454
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_description       tablet
_exptl_crystal_F_000             4840
_exptl_crystal_size_max          0.336
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.044
_refine_diff_density_max         1.842
_refine_diff_density_min         -1.934
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1451
_refine_ls_number_reflns         20394
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0722
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0854P)^2^+27.7337P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1908
_refine_ls_wR_factor_ref         0.1934
_reflns_Friedel_coverage         0.000
_reflns_number_gt                18943
_reflns_number_total             20394
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02969_si_002.cif
_cod_data_source_block           nd1606
_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_formula_moiety     '4(C28 H25 O9), 4(C H2 Cl2), H2 O'
_cod_original_formula_sum        'C112 H106 Cl8 O37'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     2327.56
_cod_database_code               1544343
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.461
_shelx_estimated_absorpt_t_max   0.889
_diffrn_source_monochromator     'MONTEL Multi-layer'
_shelx_res_checksum              9049
_shelx_hkl_checksum              16926