Tandem Achmatowicz Rearrangement and Acetalization of 1-[5-(Hydroxyalkyl)-furan-2-yl]-cyclobutanols Leading to Dispiroacetals and Subsequent Ring-Expansion to Form 6,7-Dihydrobenzofuran-4(5 H)-ones.
Peng, Hui; Luo, Wenkun; Jiang, Huanfeng; Yin, Biaolin; The Journal of organic chemistry 83 (2018) 12869–12879; doi:10.1021/acs.joc.8b01765

data_4035413
_publ_section_title
;
 Tandem Achmatowicz Rearrangement and Acetalization of
 1-[5-(Hydroxyalkyl)-furan-2-yl]-cyclobutanols Leading to Dispiroacetals
 and Subsequent Ring-Expansion to Form 6,7-Dihydrobenzofuran-4(5 H)-ones.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12869
_journal_page_last               12879
_journal_paper_doi               10.1021/acs.joc.8b01765
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H20 O4, H2 O'
_chemical_formula_sum            'C18 H22 O5'
_chemical_formula_weight         318.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.193(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.8930(5)
_cell_length_b                   9.7900(3)
_cell_length_c                   9.2333(3)
_cell_measurement_reflns_used    6137
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      69.085
_cell_measurement_theta_min      2.987
_cell_volume                     1586.65(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_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    -65.00  33.00   1.00    1.00    --  -40.98  37.00 150.00   98
  2  \w   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00   0.00  109
  3  \w     17.00 115.00   1.00    1.00    --   40.98  37.00-150.00   98
  4  \w     23.00  97.00   1.00    1.00    --   40.98-125.00-120.00   74
  5  \w     17.00 115.00   1.00    1.00    --   40.98  37.00 -90.00   98
  6  \w     94.00 178.00   1.00    1.00    --  106.95 125.00 120.00   84
  7  \w     34.00 121.00   1.00    1.00    --  106.95-125.00   0.00   87
  8  \w     79.00 178.00   1.00    1.00    --  106.95  30.00 150.00   99
  9  \w     94.00 178.00   1.00    1.00    --  106.95 125.00   0.00   84
 10  \w     78.00 178.00   1.00    1.00    --  106.95  61.00-180.00  100
 11  \w     79.00 178.00   1.00    1.00    --  106.95  30.00 -90.00   99
 12  \w     79.00 178.00   1.00    1.00    --  106.95  30.00  90.00   99
 13  \w     34.00 137.00   1.00    1.00    --  106.95 -68.00 -29.00  103
 14  \w     78.00 178.00   1.00    1.00    --  106.95  61.00-150.00  100
 15  \w     94.00 178.00   1.00    1.00    --  106.95 125.00 -60.00   84
 16  \w   -117.00 -29.00   1.00    1.00    --  -40.98 -77.00 -90.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0661168000
_diffrn_orient_matrix_UB_12      0.0971142000
_diffrn_orient_matrix_UB_13      -0.0135393000
_diffrn_orient_matrix_UB_21      -0.0103376000
_diffrn_orient_matrix_UB_22      0.0737024000
_diffrn_orient_matrix_UB_23      0.1420208000
_diffrn_orient_matrix_UB_31      0.0567466000
_diffrn_orient_matrix_UB_32      -0.0994383000
_diffrn_orient_matrix_UB_33      0.0928136000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6656
_diffrn_reflns_point_group_measured_fraction_full 0.819
_diffrn_reflns_point_group_measured_fraction_max 0.799
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.472
_diffrn_reflns_theta_min         5.039
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.795
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 952 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2557
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0324
_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^)+(0.0495P)^2^+1.0353P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0854
_reflns_Friedel_coverage         0.618
_reflns_Friedel_fraction_full    0.640
_reflns_Friedel_fraction_max     0.612
_reflns_number_gt                2549
_reflns_number_total             2557
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01765_si_002.cif
_cod_data_source_block           p_3_316
_cod_database_code               4035413
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.925
_shelx_estimated_absorpt_t_min   0.857
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB)
2.b Ternary CH refined with riding coordinates:
 C3(H3)
2.c Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C4(H4A,H4B), C17(H17A,H17B), C2(H2A,H2B)
2.d Aromatic/amide H refined with riding coordinates:
 C14(H14), C13(H13), C7(H7), C10(H10), C11(H11)
2.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
2.f Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              85685
_shelx_hkl_checksum              52397
_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 6.660
_oxdiff_exptl_absorpt_empirical_full_min 0.609