α,β-Unsaturated butenolides in an organocatalytic doubly annulative cascade for the preparation of 3,4-dihydrocoumarins.
Kowalczyk-Dworak, Dorota; Albrecht, Łukasz; Organic & biomolecular chemistry 17 (2019) 2624–2628; doi:10.1039/c9ob00068b

data_7156671
_publ_section_title
;
 \a,\b-Unsaturated butenolides in an organocatalytic doubly annulative
 cascade for the preparation of 3,4-dihydrocoumarins.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2624
_journal_page_last               2628
_journal_paper_doi               10.1039/c9ob00068b
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H23 N O5, C H2 Cl2'
_chemical_formula_sum            'C29 H25 Cl2 N O5'
_chemical_formula_weight         538.40
_chemical_name_systematic
;
(2R,3R,3aR,9bR)-3a-(2-oxo-2-phenylethyl)-3-phenyl-3,3a,4',5'-tetrahydro-1H,2'H-spiro[chromeno[4,3-b]pyrrole-2,3'-furan]-2',4(9bH)-dione
;
_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'
_audit_update_record
;
2019-01-08 deposited with the CCDC.
2019-02-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.055(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4706(1)
_cell_length_b                   12.9944(1)
_cell_length_c                   17.0882(1)
_cell_measurement_reflns_used    79041
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      79.211
_cell_measurement_theta_min      3.867
_cell_volume                     2537.15(3)
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_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  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_av_unetI/netI     0.0043
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16588
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        66.59
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_min         3.87
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.648
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.190
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.16b (Rigaku Oxford Diffraction, 2015)
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    1.410
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.505
_exptl_crystal_size_mid          0.226
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.017(4)
_refine_ls_extinction_coef       0.0009(2)
_refine_ls_extinction_expression FC^*^=KFC[1+0.001XFC^2^\L^3^/SIN(2\Q)]^-1/4^
_refine_ls_extinction_method     'shelxl-2018/3 (sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     677
_refine_ls_number_reflns         16588
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.907
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0551P)^2^+1.1668P] WHERE P=(FO^2^+2FC^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0867
_reflns_number_gt                16469
_reflns_number_total             16588
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c9ob00068b2.cif
_cod_data_source_block           dk260
_cod_depositor_comments          'Adding full bibliography for 7156671.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7156671
_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_shelx_res_checksum              55996