Doubly vinylogous and doubly rearomative functionalization of 2-alkyl-3-furfurals.
Przydacz, Artur; Dyguda, Mateusz; Topolska, Aleksandra; Skrzyńska, Anna; Xu, Chang-Jiang; Chen, Ying-Chun; Albrecht, Łukasz; Organic & biomolecular chemistry 18 (2020) 5816–5821; doi:10.1039/d0ob00788a

data_7157575
_publ_section_title
;
 Doubly vinylogous and doubly rearomative functionalization of
 2-alkyl-3-furfurals.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5816
_journal_page_last               5821
_journal_paper_doi               10.1039/d0ob00788a
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C33 H35 F O3'
_chemical_formula_sum            'C33 H35 F O3'
_chemical_formula_weight         498.61
_chemical_name_systematic
;
2-((1S,2R)-2-(3,5-di-tert-butyl-4-hydroxyphenyl)-1-(2-fluorophenyl)-2-phenylethyl)furan-3-carbaldehyde
;
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2019-11-05 deposited with the CCDC.	2020-07-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.550(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2914(1)
_cell_length_b                   14.7113(2)
_cell_length_c                   9.9029(1)
_cell_measurement_reflns_used    33987
_cell_measurement_temperature    100
_cell_measurement_theta_max      78.83
_cell_measurement_theta_min      4.47
_cell_volume                     1349.35(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            39150
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        67.68
_diffrn_reflns_theta_max         70.07
_diffrn_reflns_theta_min         4.48
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.592
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       Prism
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 2299 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5050
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0313
_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^)+(0.0617P)^2^+0.2406P] WHERE P=(FO^2^+2FC^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.0931
_reflns_number_gt                4950
_reflns_number_total             5050
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            d0ob00788a2.cif
_cod_data_source_block           AS-TITUT
_cod_depositor_comments
;Adding full bibliography for 7157575.cif.

 Adding full bibliography for 7157575.cif.
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7157575
_exptl_absorpt_empirical_full_min 0.768
_exptl_absorpt_empirical_full_max 1.375
_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelx_res_checksum              81285