Dearomative, aminocatalytic formal normal-electron-demand aza-Diels-Alder cycloaddition in the synthesis of tetrahydrofuropyridines.
Dyguda, Mateusz; Przydacz, Artur; Albrecht, Łukasz; Chemical communications (Cambridge, England) 59 (2023) 12903–12906; doi:10.1039/d3cc03946c

data_7132293
_publ_section_title
;
 Dearomative, aminocatalytic formal normal-electron-demand aza-Diels-Alder
 cycloaddition in the synthesis of tetrahydrofuropyridines.
;
_journal_issue                   86
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12903
_journal_page_last               12906
_journal_paper_doi               10.1039/d3cc03946c
_journal_volume                  59
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H22 N2 O2 S'
_chemical_formula_sum            'C27 H22 N2 O2 S'
_chemical_formula_weight         438.53
_chemical_name_systematic
;
(6R,7S)-5-(benzo[d]thiazol-2-yl)-6-(3-methoxyphenyl)-7-phenyl-4,5,6,7-tetrahydrofuro[3,2-c]pyridine
;
_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   geom
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2023-05-25 deposited with the CCDC.	2023-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.691(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3277(1)
_cell_length_b                   26.9016(1)
_cell_length_c                   9.3909(1)
_cell_measurement_reflns_used    101758
_cell_measurement_temperature    100
_cell_measurement_theta_max      78.6330
_cell_measurement_theta_min      3.2770
_cell_volume                     2245.02(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0290
_diffrn_reflns_av_unetI/netI     0.0096
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            112889
_diffrn_reflns_theta_full        67.68
_diffrn_reflns_theta_max         67.74
_diffrn_reflns_theta_min         3.29
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.491
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.397
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.79a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       prism
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 3911 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(4)
_refine_ls_extinction_coef       0.00056(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     580
_refine_ls_number_reflns         8120
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0222
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0384P)^2^+0.4136P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0599
_refine_ls_wR_factor_ref         0.0600
_reflns_number_gt                8091
_reflns_number_total             8120
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            d3cc03946c2.cif
_cod_data_source_block           BDP2
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7132293
_shelx_res_checksum              44824