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_4035412
_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_formula_moiety         'C24 H24 N4 O6'
_chemical_formula_sum            'C24 H24 N4 O6'
_chemical_formula_weight         464.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-04-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.959(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.0590(18)
_cell_length_b                   15.9883(7)
_cell_length_c                   11.3279(6)
_cell_measurement_reflns_used    2825
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.5610
_cell_measurement_theta_min      3.2590
_cell_volume                     4470.1(5)
_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)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.972
_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  66.00   1.00    5.00    --   40.98 -38.00 -30.00   46
  2  \w     37.00 135.00   1.00    5.00    --  106.95 -61.00  60.00   98
  3  \w    135.00 160.00   1.00    5.00    --  106.95 -15.00  30.00   25
  4  \w    144.00 178.00   1.00    5.00    --  106.95  61.00  30.00   34
  5  \w    153.00 178.00   1.00    5.00    --  106.95 125.00 -90.00   25
  6  \w    148.00 178.00   1.00    5.00    --  106.95 125.00-150.00   30
  7  \w     84.00 120.00   1.00    5.00    --  106.95  77.00 -90.00   36
  8  \w     77.00 164.00   1.00    5.00    --  106.95  77.00-150.00   87
  9  \w     32.00 116.00   1.00    5.00    --  106.95 -15.00  30.00   84
 10  \w    117.00 178.00   1.00    5.00    --  106.95  93.00 172.00   61
 11  \w     42.00  71.00   1.00    5.00    --   40.98-125.00-180.00   29
 12  \w    -69.00  28.00   1.00    5.00    --  -40.98  57.00 -90.00   97
 13  \w   -111.00 -51.00   1.00    5.00    --  -40.98 -57.00 120.00   60
;
_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      -0.0525288000
_diffrn_orient_matrix_UB_12      0.0400574000
_diffrn_orient_matrix_UB_13      -0.0672159000
_diffrn_orient_matrix_UB_21      -0.0316601000
_diffrn_orient_matrix_UB_22      -0.0798072000
_diffrn_orient_matrix_UB_23      0.0201194000
_diffrn_orient_matrix_UB_31      -0.0117925000
_diffrn_orient_matrix_UB_32      0.0361437000
_diffrn_orient_matrix_UB_33      0.1188695000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_av_unetI/netI     0.0855
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            18039
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.519
_diffrn_reflns_theta_min         3.293
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.839
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.380
_exptl_crystal_description       block
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     615
_refine_ls_number_reflns         8748
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.0763
_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^)+(0.0813P)^2^+1.1204P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1742
_refine_ls_wR_factor_ref         0.2010
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5771
_reflns_number_total             8748
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01765_si_003.cif
_cod_data_source_block           bh0413
_cod_original_cell_volume        4470.2(4)
_cod_database_code               4035412
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.89
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C01P(HP)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C00Z(HF,HG), C2(H2A,H2B), C9(H9A,H9B), C01M(HL,HM), C01N(HN,HO),
 C10(H10A,H10B), C01T(HQ,HR), C01V(HV,HW), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 N00B(H), N2(H2), C00N(HA), C00O(HB), C00R(HC), C00T(HD), C00U(HE), C21(H21),
 C24(H24), C7(H7), C6(H6), C23(H23), C01C(HH), C17(H17), C01E(HI), C01F(HJ),
 C14(H14), C01K(HK), C13(H13), C16(H16)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C01U(HS,HT,HU)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.750
_oxdiff_exptl_absorpt_empirical_full_min 0.661