Efficient Oxa-Diels–Alder/Semipinacol Rearrangement/Aldol Cascade Reaction: Short Approach to Polycyclic Architectures
Peng, Jin-Bao; Qi, Yue; Jing, Ze-Ran; Wang, Shao-Hua; Tu, Yong-Qiang; Zhu, Dao-Yong; Zhang, Fu-Min; Organic Letters  (2015) 150209135056006–; doi:10.1021/acs.orglett.5b00125

data_1518711
_publ_section_title
;
 Efficient Oxa-Diels--Alder/Semipinacol Rearrangement/Aldol Cascade
 Reaction: Short Approach to Polycyclic Architectures
;
_journal_name_full               'Organic Letters'
_journal_page_first              150209135056006
_journal_paper_doi               10.1021/acs.orglett.5b00125
_journal_year                    2015
_chemical_formula_moiety         'C15 H22 O5'
_chemical_formula_sum            'C15 H22 O5'
_chemical_formula_weight         282.33
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-01-28
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.261(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.3435(10)
_cell_length_b                   7.2491(5)
_cell_length_c                   15.3576(9)
_cell_measurement_reflns_used    1955
_cell_measurement_temperature    290.04(10)
_cell_measurement_theta_max      28.6606
_cell_measurement_theta_min      3.1016
_cell_volume                     1484.36(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      290.04(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -19.00    8.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3492  -99.0000   60.0000 27

  2 omega  -86.00  -57.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3492  178.0000  150.0000 29

  3 omega   35.00   84.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000   90.0000 49

  4 omega   -1.00   88.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000  120.0000 89

  5 omega    1.00   46.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000 -120.0000 45

  6 omega   29.00   74.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   38.0000 -120.0000 45
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0322763000
_diffrn_orient_matrix_UB_12      0.0696747000
_diffrn_orient_matrix_UB_13      -0.0172685000
_diffrn_orient_matrix_UB_21      0.0348670000
_diffrn_orient_matrix_UB_22      0.0197058000
_diffrn_orient_matrix_UB_23      -0.0325091000
_diffrn_orient_matrix_UB_31      -0.0239583000
_diffrn_orient_matrix_UB_32      -0.0656548000
_diffrn_orient_matrix_UB_33      -0.0280138000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6404
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.11
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
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    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2916
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0572
_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^)+(0.0580P)^2^+1.0071P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1401
_refine_ls_wR_factor_ref         0.1554
_reflns_number_gt                2231
_reflns_number_total             2916
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b00125_si_005.cif
_cod_data_source_block           pengjb0107
_cod_original_cell_volume        1484.37(17)
_cod_database_code               1518711
_reflns_odcompleteness_completeness 99.54
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C11B) \\sim Ueq, Uanis(C11A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Fixed Sof: H10A(0.65) H10B(0.65) H10C(0.35) H10D(0.35) H13C(0.65) H13D(0.65)
 H13A(0.35) H13B(0.35) H15C(0.65) H15D(0.65) H15A(0.35) H15B(0.35) C11B(0.35)
 H11A(0.35) H11B(0.35) H11C(0.35) C12A(0.65) H12A(0.65) H12B(0.65) C11A(0.65)
 H11D(0.65) H11E(0.65) H11F(0.65) C12B(0.35) H12C(0.35) H12D(0.35)
4.a Ternary CH refined with riding coordinates:
 C5(H5A)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C10(H10A,H10B), C10(H10C,
 H10D), C13(H13C,H13D), C13(H13A,H13B), C15(H15C,H15D), C15(H15A,H15B),
 C12A(H12A,H12B), C12B(H12C,H12D)
4.c Aromatic/amide H refined with riding coordinates:
 C7(H7)
4.d Idealised Me refined as rotating group:
 C11B(H11A,H11B,H11C), C11A(H11D,H11E,H11F)
4.e Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'