Electroorganocatalytic asymmetric Diels–Alder cycloaddition of hydroquinones with α,β-unsaturated aldehydes
Pomikło, Dominika; Romaniuk, Krzysztof; Sieroń, Lesław; Albrecht, Anna; Chemical Communications 61 (2025) 6655–6658; doi:10.1039/D5CC00505A

data_7134386
_publ_section_title
;
 Electroorganocatalytic asymmetric Diels--Alder cycloaddition of
 hydroquinones with \a,\b-unsaturated aldehydes
;
_journal_issue                   36
_journal_name_full               'Chemical Communications'
_journal_page_first              6655
_journal_page_last               6658
_journal_paper_doi               10.1039/D5CC00505A
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H18 O2'
_chemical_formula_sum            'C16 H18 O2'
_chemical_formula_weight         242.30
_chemical_name_systematic
;
(4aR,4bR)-3,4a-dimethyl-4a,4b,5,6,7,8-hexahydrophenanthrene-1,4-dione
;
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2024-09-11 deposited with the CCDC.	2025-03-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3279(1)
_cell_length_b                   8.1376(1)
_cell_length_c                   25.4842(1)
_cell_measurement_reflns_used    59178
_cell_measurement_temperature    100
_cell_measurement_theta_max      78.602
_cell_measurement_theta_min      3.460
_cell_volume                     1312.28(3)
_computing_cell_refinement       'CrysAlisPro 1.171.43.131a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.131a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.131a (Rigaku OD, 2024)'
_computing_structure_refinement  'SHELXL-2019/3 (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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0451
_diffrn_reflns_av_unetI/netI     0.0088
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            65972
_diffrn_reflns_theta_full        67.68
_diffrn_reflns_theta_max         67.71
_diffrn_reflns_theta_min         3.47
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.627
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_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.131a (Rigaku Oxford Diffraction, 2024)
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            yellow
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_description       prism
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.123
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 958 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_coef       0.0061(7)
_refine_ls_extinction_expression FC^*^=KFC[1+0.001XFC^2^\L^3^/SIN(2\Q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/3 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2369
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0241
_refine_ls_R_factor_gt           0.0241
_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^)+(0.0307P)^2^+0.2821P] WHERE P=(FO^2^+2FC^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0625
_refine_ls_wR_factor_ref         0.0625
_reflns_number_gt                2368
_reflns_number_total             2369
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            d5cc00505a2.cif
_cod_data_source_block           DP84
_cod_depositor_comments          'Adding full bibliography for 7134386.cif.'
_cod_database_code               7134386
_shelx_res_checksum              52004
_shelx_hkl_checksum              62499