Phosphine-promoted intramolecular Rauhut-Currier/Wittig reaction cascade to access (hetero)arene-fused diquinanes.
Maurya, Jay Prakash; Swain, Subham S.; Ramasastry, S. S. V.; Organic & biomolecular chemistry 22 (2024) 5718–5723; doi:10.1039/d4ob00984c

data_7159995
_publ_section_title
;
 Phosphine-promoted intramolecular Rauhut-Currier/Wittig reaction cascade
 to access (hetero)arene-fused diquinanes.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5718
_journal_page_last               5723
_journal_paper_doi               10.1039/d4ob00984c
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C26 H22 O2'
_chemical_formula_sum            'C26 H22 O2'
_chemical_formula_weight         366.44
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-01-15
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-01-15 deposited with the CCDC.	2024-06-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3208(6)
_cell_length_b                   12.3275(7)
_cell_length_c                   16.0767(12)
_cell_measurement_reflns_used    1839
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.4450
_cell_measurement_theta_min      3.5180
_cell_volume                     2045.4(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXH-1997  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -54.00  61.20   0.30   10.00    --   29.89  54.00 150.00  384
  2  \w    -60.00 -12.90   0.30   10.00    --   29.89  54.00 -90.00  157
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0133723000
_diffrn_orient_matrix_UB_12      0.0546743000
_diffrn_orient_matrix_UB_13      -0.0109506000
_diffrn_orient_matrix_UB_21      -0.0510099000
_diffrn_orient_matrix_UB_22      0.0014268000
_diffrn_orient_matrix_UB_23      0.0295480000
_diffrn_orient_matrix_UB_31      0.0441073000
_diffrn_orient_matrix_UB_32      0.0180369000
_diffrn_orient_matrix_UB_33      0.0308006000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5365
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.57
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_preparation       MeOH
_exptl_crystal_recrystallization_method MeOH
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.105
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         3599
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0532P)^2^+0.1146P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1057
_reflns_number_gt                3146
_reflns_number_total             3599
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4ob00984c1.cif
_cod_data_source_block           jp03-phosphine
_cod_depositor_comments
'Adding full bibliography for 7159995--7159996.cif.'
_cod_database_code               7159995
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.277
_oxdiff_exptl_absorpt_empirical_full_min 0.824