One-pot synthesis of benzofused 8-oxabicyclo[3.3.1]nonanes <i>via</i> GaCl<sub>3</sub>-mediated cyclocondensation of <i>o</i>-allylbenzaldehydes and 1,3-dicarbonyl synthons.
Chang, Meng-Yang; Lee, Yan-Ling; Organic & biomolecular chemistry 22 (2024) 1646–1653; doi:10.1039/d4ob00016a

data_7159782
_publ_section_title
;
 One-pot synthesis of benzofused 8-oxabicyclo[3.3.1]nonanes <i>via</i>
 GaCl<sub>3</sub>-mediated cyclocondensation of
 <i>o</i>-allylbenzaldehydes and 1,3-dicarbonyl synthons.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1646
_journal_page_last               1653
_journal_paper_doi               10.1039/d4ob00016a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C21 H18 O4'
_chemical_formula_sum            'C21 H18 O4'
_chemical_formula_weight         334.35
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-09-26
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-11-23 deposited with the CCDC.	2024-01-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   36.9306(9)
_cell_length_b                   36.9306(9)
_cell_length_c                   6.4911(2)
_cell_measurement_reflns_used    17815
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.7300
_cell_measurement_theta_min      1.8890
_cell_volume                     7666.9(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -15.00 100.00   0.50    1.92    --   10.60  77.00  90.00  230
  2  \w    -17.00 100.00   0.50    1.92    --   10.60  82.00  60.00  234
  3  \w    -15.00 100.00   0.50    1.92    --   10.60  77.00 -90.00  230
  4  \w    -79.00 100.00   0.50    1.92    --   10.60  19.00-180.00  358
  5  \w    -17.00 100.00   0.50    1.92    --   10.60  82.00 150.00  234
  6  \w    -17.00 100.00   0.50    1.92    --   10.60  82.00  30.00  234
  7  \w    -17.00 100.00   0.50    1.92    --   10.60  82.00 -60.00  234
  8  \w    -17.00 100.00   0.50    1.92    --   10.60  82.00-180.00  234
  9  \w    -20.00 100.00   0.50    1.92    --   10.60  57.00 -90.00  240
 10  \w   -100.00  14.00   0.50    1.92    --  -10.90 -82.00   0.00  228
 11  \w    -36.00  29.00   0.50    1.92    --  -10.90  77.00  60.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0960
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            51392
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.990
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_min         1.910
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.18262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       needle
_exptl_crystal_F_000             3168
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.793
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3005
_refine_ls_number_restraints     126
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0662P)^2^+9.2604P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1294
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2526
_reflns_number_total             3005
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00016a2.cif
_cod_data_source_block           k11109-myc-g(ynb908)_auto
_cod_depositor_comments
'Adding full bibliography for 7159780--7159782.cif.'
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               7159782
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.965
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8)
\\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C18) \\sim Ueq,
Uanis(C11) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C4) \\sim
Ueq, Uanis(C1) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C14)
\\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C2) \\sim Ueq,
Uanis(C15) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C20) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.005
3.a Ternary CH refined with riding coordinates:
 C9(H9), C1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C2(H2A,H2B)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C17(H17), C14(H14), C16(H16), C15(H15)
3.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              42632
_shelx_fab_checksum              97084
_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
;