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_7123084
_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_formula_moiety         'C38 H31 Br3 O9'
_chemical_formula_sum            'C38 H31 Br3 O9'
_chemical_formula_weight         871.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-11-27
_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                93.234(7)
_cell_angle_beta                 99.276(6)
_cell_angle_gamma                105.176(7)
_cell_formula_units_Z            2
_cell_length_a                   9.7677(7)
_cell_length_b                   13.6042(12)
_cell_length_c                   14.1949(11)
_cell_measurement_reflns_used    4283
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      69.7420
_cell_measurement_theta_min      4.7650
_cell_volume                     1787.0(3)
_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 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details
;
  1 omega   21.00   58.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   63.0000   30.0000 25

  2 omega  -70.00  -31.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -77.0000  -90.0000 26

  3 omega  -25.00   15.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -77.0000  -90.0000 27

  4 omega  -57.00   -3.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000   30.0000 36

  5 omega   94.00  121.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   90.0000 18

  6 omega  -13.00   75.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  150.0000 59

  7 omega   36.00   79.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   90.0000 29

  8 omega    0.00   73.50   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -30.0000 49

  9 omega   33.00  123.00   1.5000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -60.0000 60

 10 omega   69.00   94.50   1.5000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   60.0000 17

 11 omega   89.00  114.50   1.5000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 17

 12 omega   90.00  115.50   1.5000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 17

 13 omega   50.00  102.50   1.5000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -150.0000 35

 14 omega   43.00   92.50   1.5000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 33

 15 omega   47.00   83.00   1.5000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -30.0000 24

 16 omega   40.00   94.00   1.5000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   30.0000 36

 17 omega   38.00   77.00   1.5000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 26

 18 omega   38.00   77.00   1.5000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 26

 19 omega   73.00  145.00   1.5000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000  120.0000 48

 20 omega   36.00  102.00   1.5000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 44

 21 omega   85.00  112.00   1.5000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000   60.0000 18

 22 omega   74.00  120.50   1.5000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000   90.0000 31

 23 omega   40.00   88.00   1.5000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  120.0000 32

 24 omega   49.00  103.00   1.5000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   30.0000 36

 25 omega   62.00   92.00   1.5000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -120.0000 20

 26 omega   35.00  156.50   1.5000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000  -90.0000 81

 27 omega   86.00  176.00   1.5000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -60.0000 60

 28 omega   36.00  145.50   1.5000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000 -150.0000 73
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0629786000
_diffrn_orient_matrix_UB_12      0.0888169000
_diffrn_orient_matrix_UB_13      0.0248051000
_diffrn_orient_matrix_UB_21      0.1086867000
_diffrn_orient_matrix_UB_22      0.0288883000
_diffrn_orient_matrix_UB_23      0.0953985000
_diffrn_orient_matrix_UB_31      0.1088475000
_diffrn_orient_matrix_UB_32      0.0720649000
_diffrn_orient_matrix_UB_33      -0.0500763000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11257
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         4.394
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.653
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68801
_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    1.619
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         6101
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0321
_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^)+(0.0362P)^2^+0.7034P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0842
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5142
_reflns_number_total             6101
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc00811j2.cif
_cod_data_source_block           liul_1127
_cod_database_code               7123084
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 96.66
_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
2.a Ternary CH refined with riding coordinates:
 C16(H16), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C29(H29A,H29B), C30(H30A,
 H30B), C31(H31A,H31B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C24(H24), C25(H25),
 C27(H27), C28(H28), C34(H34), C35(H35), C37(H37), C38(H38)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              6006
_shelx_hkl_checksum              43789
_olex2_date_sample_data_collection 2018-11-27
_olex2_submission_special_instructions 'No special instructions were received'