A Catalytic Asymmetric One-Pot [3+2] Cyclization/Semipinacol Rearrangement Sequence: An Efficient Construction of MultiSubstituted 3H-Spiro[benzofuran-2,1'-cyclopentane] Skeleton
Liu, Lin; Lei, Lin-Sheng; Zhan, Zong-Song; Liu, Si-Zhan; Wang, Yu-Xiao; Tu, Yong Qiang; Zhang, Fu-Min; Zhang, Xiao-Ming; Ma, Ai-Jun; Wang, Shao-Hua; Chemical Communications  (2019) –; doi:10.1039/C9CC00811J

data_7123085
_publ_section_title
;
 A Catalytic Asymmetric One-Pot [3+2] Cyclization/Semipinacol
 Rearrangement Sequence: An Efficient Construction of MultiSubstituted
 3H-Spiro[benzofuran-2,1'-cyclopentane] Skeleton
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC00811J
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H28 O6'
_chemical_formula_sum            'C29 H28 O6'
_chemical_formula_weight         472.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_symmetry_space_group_name_Hall  'I 2y'
_symmetry_space_group_name_H-M   'I 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-11-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-12-07 deposited with the CCDC.    2019-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.178(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.3050(4)
_cell_length_b                   7.58059(15)
_cell_length_c                   19.3663(4)
_cell_measurement_reflns_used    6360
_cell_measurement_temperature    291.53(15)
_cell_measurement_theta_max      69.8770
_cell_measurement_theta_min      4.8190
_cell_volume                     2399.52(10)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      291.53(15)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
  1 omega  -45.00   14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -63.0000  -90.0000 59

  2 omega   26.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   25.0000    0.0000 40

  3 omega  -25.00    4.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000   30.0000 29

  4 omega  -75.00  -47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -63.0000  -90.0000 28

  5 omega  -37.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   25.0000    0.0000 26

  6 omega   42.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -30.0000 62

  7 omega  -14.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000 -120.0000 88

  8 omega   58.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   30.0000 65

  9 omega  -17.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000  120.0000 88

 10 omega   36.00   67.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -90.0000 31

 11 omega  115.00  165.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 50

 12 omega   85.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  -90.0000 25

 13 omega   81.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000   30.0000 30

 14 omega   81.00  120.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  -30.0000 39

 15 omega   85.00  174.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -60.0000 89

 16 omega  111.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   74.0000  -46.4636 67

 17 omega  129.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 46

 18 omega   76.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 27

 19 omega   40.00   67.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   30.0000 27

 20 omega  119.00  156.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 37

 21 omega  130.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   12.0000 -120.0000 46

 22 omega   77.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 26

 23 omega   88.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000    0.0000 25

 24 omega   76.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 35

 25 omega  111.00  172.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  120.0000 61

 26 omega   85.00  131.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -150.0000 46

 27 omega   76.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 28

 28 omega   85.00  157.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000   30.0000 72

 29 omega   35.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -30.0000 55

 30 omega  145.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000   60.0000 32

 31 omega   83.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000   60.0000 29

 32 omega   81.00  107.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000    0.0000 26

 33 omega   82.00  174.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000 -180.0000 92

 34 omega   77.00  102.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 25

 35 omega  133.00  162.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 29

 36 omega   78.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000   60.0000 27

 37 omega   84.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  -30.0000 26

 38 omega   96.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000  120.0000 80

 39 omega   85.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   19.1861 27

 40 omega   78.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   30.0000 25

 41 omega   85.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000    0.0000 27

 42 omega   86.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -30.0000 25

 43 omega   78.00  104.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   74.0000  -46.4636 26

 44 omega   68.00   95.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   22.0000   89.5751 27
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0764791000
_diffrn_orient_matrix_UB_12      -0.1178562000
_diffrn_orient_matrix_UB_13      0.0168289000
_diffrn_orient_matrix_UB_21      0.0094649000
_diffrn_orient_matrix_UB_22      0.0038927000
_diffrn_orient_matrix_UB_23      0.0819251000
_diffrn_orient_matrix_UB_31      -0.0542787000
_diffrn_orient_matrix_UB_32      -0.1654721000
_diffrn_orient_matrix_UB_33      -0.0101257000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9602
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        66.561
_diffrn_reflns_theta_max         66.561
_diffrn_reflns_theta_min         4.835
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.742
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62718
_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    1.308
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 1676 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4024
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0558P)^2^+0.5379P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1014
_reflns_Friedel_coverage         0.781
_reflns_Friedel_fraction_full    0.905
_reflns_Friedel_fraction_max     0.905
_reflns_number_gt                3921
_reflns_number_total             4024
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc00811j2.cif
_cod_data_source_block           liul_1125
_cod_database_code               7123085
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.916
_shelx_estimated_absorpt_t_min   0.848
_reflns_odcompleteness_completeness 98.28
_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
2. Restrained distances
 O6-H6
 0.86 with sigma of 0.01
 H6-O5
 2.5 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C15(H15A,H15B), C17(H17A,H17B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25),
 C26(H26), C27(H27), C28(H28), C29(H29)
3.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
3.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O6(H6)
;
_shelx_res_checksum              19216
_shelx_hkl_checksum              43381
_olex2_date_sample_data_collection 2018-11-25
_olex2_submission_special_instructions 'No special instructions were received'