A micelle-mediated approach enables facile access to bridged oxabicyclo[<i>n</i>.3.1]alkene scaffolds.
Wani, Mohmad Muzafar; Rashid, Auqib; Bhat, Bilal A.; Organic & biomolecular chemistry 21 (2023) 6151–6159; doi:10.1039/d3ob00918a

data_7159464
_publ_section_title
;
 A micelle-mediated approach enables facile access to bridged
 oxabicyclo[<i>n</i>.3.1]alkene scaffolds.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6151
_journal_page_last               6159
_journal_paper_doi               10.1039/d3ob00918a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C16 H18 O4'
_chemical_formula_sum            'C16 H18 O4'
_chemical_formula_weight         274.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-04-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-04-10 deposited with the CCDC.	2023-07-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.689(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8721(2)
_cell_length_b                   21.5158(7)
_cell_length_c                   12.7252(4)
_cell_measurement_reflns_used    5456
_cell_measurement_temperature    293(10)
_cell_measurement_theta_max      21.8440
_cell_measurement_theta_min      2.4850
_cell_volume                     1589.29(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_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     -9.00  39.00   0.50    2.20    --   16.22  30.00  30.00   96
  2  \w     55.00  86.00   0.50    2.20    --   16.22  30.00  30.00   62
  3  \w     -2.00  85.00   0.50    2.20    --   16.22  30.00 -60.00  174
  4  \w      4.00  65.00   0.50    2.20    --   16.22-116.00 -33.00  122
  5  \w    -35.00  22.00   0.50    2.20    --  -14.97 -94.00 -30.00  114
  6  \w     -4.00  41.00   0.50    2.20    --   16.22 -45.00  90.00   90
  7  \w    -32.00  19.00   0.50    2.20    --  -14.97 -94.00 150.00  102
  8  \w     32.00  94.00   0.50    2.20    --   16.22-166.00 179.00  124
  9  \w    -30.00  12.00   0.50    2.20    --  -14.97 -61.00 150.00   84
 10  \w    -53.00  -7.00   0.50    2.20    --   16.22 -45.00  90.00   92
 11  \w    -67.00 -35.00   0.50    2.20    --  -14.97 -61.00 150.00   64
 12  \w    -91.00 -45.00   0.50    2.20    --  -14.97-166.00 179.00   92
 13  \w    -64.00  -3.00   0.50    2.20    --  -14.97 116.00  54.00  122
 14  \w    -61.00 -15.00   0.50    2.20    --  -14.97 125.00  60.00   92
 15  \w    -93.00 -31.00   0.50    2.20    --  -14.97 166.00-158.00  124
 16  \w     45.00  92.00   0.50    2.20    --   16.22 166.00-158.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0166216000
_diffrn_orient_matrix_UB_12      0.0320130000
_diffrn_orient_matrix_UB_13      0.0097939000
_diffrn_orient_matrix_UB_21      -0.0157217000
_diffrn_orient_matrix_UB_22      0.0059061000
_diffrn_orient_matrix_UB_23      -0.0554709000
_diffrn_orient_matrix_UB_31      -0.1200013000
_diffrn_orient_matrix_UB_32      -0.0052184000
_diffrn_orient_matrix_UB_33      -0.0027583000
_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  0.0319
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16638
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.957
_diffrn_reflns_theta_min         1.875
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
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    1.146
_exptl_crystal_description       needle
_exptl_crystal_F_000             584
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.1059
_refine_ls_R_factor_gt           0.0607
_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^)+(0.0989P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1760
_refine_ls_wR_factor_ref         0.1994
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1766
_reflns_number_total             3323
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00918a2.cif
_cod_data_source_block           gm57
_cod_depositor_comments          'Adding full bibliography for 7159464.cif.'
_cod_database_code               7159464
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O '
_reflns_odcompleteness_completeness 99.29
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C10(H10A,H10B), C6(H6A,H6B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,
 H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C16(H16), C15(H15)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              75362
_shelx_fab_checksum              75379
_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 1.291
_oxdiff_exptl_absorpt_empirical_full_min 0.622