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_7159781
_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 H19 N O3'
_chemical_formula_sum            'C21 H19 N O3'
_chemical_formula_weight         333.37
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-23
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-11-23 deposited with the CCDC.	2024-01-29 downloaded from the CCDC.
;
_cell_angle_alpha                103.452(2)
_cell_angle_beta                 95.930(2)
_cell_angle_gamma                103.910(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3860(2)
_cell_length_b                   8.6370(2)
_cell_length_c                   12.3414(3)
_cell_measurement_reflns_used    10065
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      26.7580
_cell_measurement_theta_min      2.5080
_cell_volume                     831.78(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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.953
_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    -20.00 100.00   0.50    2.02    --   10.60  57.00 150.00  240
  2  \w    -79.00  41.00   0.50    2.02    --   10.60 -57.00 -90.00  240
  3  \w    -17.00 100.00   0.50    2.02    --   10.60  82.00-180.00  234
  4  \w    -17.00 100.00   0.50    2.02    --   10.60  82.00  60.00  234
  5  \w    -20.00 100.00   0.50    2.02    --   10.60  57.00 -30.00  240
  6  \w    -15.00 100.00   0.50    2.02    --   10.60  77.00  30.00  230
  7  \w    -17.00 100.00   0.50    2.02    --   10.60  82.00-120.00  234
  8  \w    -79.00  48.00   0.50    2.02    --   10.60 -37.00 -60.00  254
  9  \w   -100.00  17.00   0.50    2.02    --  -10.90 -82.00-150.00  234
 10  \w   -100.00  15.00   0.50    2.02    --  -10.90 -77.00-120.00  230
 11  \w    -41.00  68.00   0.50    2.02    --  -10.90  57.00 150.00  218
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0541518000
_diffrn_orient_matrix_UB_12      -0.0517655000
_diffrn_orient_matrix_UB_13      -0.0004685000
_diffrn_orient_matrix_UB_21      -0.0189366000
_diffrn_orient_matrix_UB_22      -0.0265372000
_diffrn_orient_matrix_UB_23      -0.0598671000
_diffrn_orient_matrix_UB_31      0.0672622000
_diffrn_orient_matrix_UB_32      0.0657417000
_diffrn_orient_matrix_UB_33      -0.0031860000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18919
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.058
_diffrn_reflns_theta_min         1.721
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64261
_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    1.331
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3472
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0514P)^2^+0.1384P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1077
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2865
_reflns_number_total             3472
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00016a2.cif
_cod_data_source_block           k11211-myc-h(ynb1013)_auto
_cod_depositor_comments
'Adding full bibliography for 7159780--7159782.cif.'
_cod_database_code               7159781
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.974
_reflns_odcompleteness_completeness 99.18
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Ternary CH refined with riding coordinates:
 C10(H009), C20(H00M)
2.b Secondary CH2 refined with riding coordinates:
 C19(H00D,H00E), C21(H00H,H00I)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H00A), C2(H00B), C5(H00C), C12(H00F), C4(H00G), C3(H00K), C13(H00L)
2.d Idealised Me refined as rotating group:
 C16(H00J,H00N,H00O), C15(H00P,H00Q,H00R)
;
_shelx_res_checksum              49183
_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 1.274
_oxdiff_exptl_absorpt_empirical_full_min 0.737