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_7159996
_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_formula_moiety         'C26 H20 O4'
_chemical_formula_sum            'C26 H20 O4'
_chemical_formula_weight         396.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-01-23
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-01-24 deposited with the CCDC.	2024-06-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.088(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5179(4)
_cell_length_b                   10.2457(5)
_cell_length_c                   23.2567(10)
_cell_measurement_reflns_used    5640
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5430
_cell_measurement_theta_min      2.6600
_cell_volume                     2026.71(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.958
_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    -69.00 118.20   0.30   25.00    --   29.89  54.00 -30.00  624
  2  \w    -69.00 118.20   0.30   25.00    --   29.89  54.00-150.00  624
  3  \w    -69.00 118.20   0.30   25.00    --   29.89  54.00  30.00  624
  4  \w    -34.00  24.20   0.30   25.00    --   29.89  54.00 -30.00  194
;
_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      0.0085450000
_diffrn_orient_matrix_UB_12      0.0011600000
_diffrn_orient_matrix_UB_13      -0.0301730000
_diffrn_orient_matrix_UB_21      -0.0814461000
_diffrn_orient_matrix_UB_22      0.0133885000
_diffrn_orient_matrix_UB_23      -0.0045670000
_diffrn_orient_matrix_UB_31      0.0159750000
_diffrn_orient_matrix_UB_32      0.0678586000
_diffrn_orient_matrix_UB_33      0.0014295000
_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  0.0442
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            31399
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.80
_diffrn_reflns_theta_min         2.65
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         7201
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0620
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0993P)^2^+0.2363P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1665
_refine_ls_wR_factor_ref         0.2108
_reflns_number_gt                4306
_reflns_number_total             7201
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4ob00984c1.cif
_cod_data_source_block           exp_639
_cod_depositor_comments
'Adding full bibliography for 7159995--7159996.cif.'
_cod_database_code               7159996
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C00F) \\sim Ueq, Uanis(C00P) \\sim Ueq, Uanis(C00T) \\sim Ueq,
Uanis(C00U) \\sim Ueq, Uanis(C00R) \\sim Ueq, Uanis(C00M) \\sim Ueq: with sigma
of 0.003 and sigma for terminal atoms of 0.006
3.a Ternary CH refined with riding coordinates:
 C005(H005), C007(H007)
3.b Secondary CH2 refined with riding coordinates:
 C00D(H00A,H00B), C00G(H00C,H00D)
3.c Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00T(H00T), C00U(H00U)
;
_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 1.786
_oxdiff_exptl_absorpt_empirical_full_min 0.530