Improved synthesis of 8-oxabicyclo[3.2.1]octanes via tandem C-H oxidation/oxa-[3,3] Cope rearrangement/aldol cyclization.
Liu, Lin; Cheng, Hai-Long; Ma, Wen-Qiang; Hou, Si-Hua; Tu, Yong-Qiang; Zhang, Fu-Min; Zhang, Xiao-Ming; Wang, Shao-Hua; Chemical communications (Cambridge, England) 54 (2018) 196–199; doi:10.1039/c7cc08511g

data_7120938
_publ_section_title
;
 Improved synthesis of 8-oxabicyclo[3.2.1]octanes via tandem C-H
 oxidation/oxa-[3,3] Cope rearrangement/aldol cyclization.
;
_journal_issue                   2
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              196
_journal_page_last               199
_journal_paper_doi               10.1039/c7cc08511g
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H18 O2'
_chemical_formula_sum            'C16 H18 O2'
_chemical_formula_weight         242.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-05-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-07-24 deposited with the CCDC.
2017-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.3031(7)
_cell_length_b                   6.1090(3)
_cell_length_c                   26.0729(16)
_cell_measurement_reflns_used    2506
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      28.0010
_cell_measurement_theta_min      3.8840
_cell_volume                     2596.7(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega  -15.00   18.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6617  -99.0000 -150.0000 33

  2 omega  -33.00    1.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.6617  -66.0000  -78.0000 34

  3 omega  -20.00   59.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.9430  -99.0000   60.0000 79

  4 omega   -2.00   93.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.9430   38.0000  -30.0000 95

  5 omega  -44.00    6.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.9430  -38.0000  150.0000 50
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0281917000
_diffrn_orient_matrix_UB_12      -0.0163376000
_diffrn_orient_matrix_UB_13      -0.0203643000
_diffrn_orient_matrix_UB_21      0.0020411000
_diffrn_orient_matrix_UB_22      -0.1147258000
_diffrn_orient_matrix_UB_23      0.0039558000
_diffrn_orient_matrix_UB_31      -0.0330682000
_diffrn_orient_matrix_UB_32      0.0068251000
_diffrn_orient_matrix_UB_33      0.0176124000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            11512
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.43
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.240
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.620
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4680
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0745
_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^)+(0.1173P)^2^+0.2943P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1810
_refine_ls_wR_factor_ref         0.2019
_reflns_number_gt                3741
_reflns_number_total             4680
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc08511g2.cif
_cod_data_source_block           liul_0519
_cod_depositor_comments          'Adding full bibliography for 7120938.cif.'
_cod_database_code               7120938
_reflns_odcompleteness_completeness 98.77
_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:
 C8(H8), C12(H12), C24(H24), C28(H28)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C13(H13A,H13B), C25(H25A,H25B), C29(H29A,H29B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C27(H27)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C31(H31A,H31B,H31C), C32(H32A,H32B,
 H32C)
;
_olex2_date_sample_data_collection 2017-05-19
_olex2_submission_special_instructions 'No special instructions were received'