Highly diastereoselective oxa-[3+3] cyclization with C,N-cyclic azomethine imines via the copper-catalyzed aerobic oxygenated C[double bond, length as m-dash]C bond of indoles.
Yu, Lemao; Zhong, Yuan; Yu, Jicong; Gan, Lu; Cai, Zhengjun; Wang, Rui; Jiang, Xianxing; Chemical communications (Cambridge, England) 54 (2018) 2353–2356; doi:10.1039/c7cc09640b

data_7121256
_publ_section_title
;
 Highly diastereoselective oxa-[3+3] cyclization with C,N-cyclic
 azomethine imines via the copper-catalyzed aerobic oxygenated C[double
 bond, length as m-dash]C bond of indoles.
;
_journal_issue                   19
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2353
_journal_page_last               2356
_journal_paper_doi               10.1039/c7cc09640b
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C32 H30 F N3 O3 S'
_chemical_formula_sum            'C32 H30 F N3 O3 S'
_chemical_formula_weight         555.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-11-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-11-06 deposited with the CCDC.
2018-02-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.2756(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.27904(5)
_cell_length_b                   18.37857(9)
_cell_length_c                   16.77742(8)
_cell_measurement_reflns_used    38622
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.3920
_cell_measurement_theta_min      2.3960
_cell_volume                     2772.80(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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   -119.00 -13.00   1.00    1.00    --  -44.52 -77.00 -90.00  106
  2  \w   -126.00 -79.00   1.00    1.00    --  -44.52 -99.00-120.00   47
  3  \w   -114.00 -19.00   1.00    1.00    --  -44.52 -57.00   0.00   95
  4  \w     73.00 118.00   1.00    1.00    --   44.52 125.00  60.00   45
  5  \w     73.00 118.00   1.00    1.00    --   44.52 125.00-120.00   45
  6  \w      2.00  98.00   1.00    1.00    --   44.52-125.00  90.00   96
  7  \w     73.00 118.00   1.00    1.00    --   44.52 125.00 -60.00   45
  8  \w   -117.00 -20.00   1.00    3.00    --  -90.00  61.00 -60.00   97
  9  \w     73.00 170.00   1.00    3.00    --  100.00  61.00  90.00   97
 10  \w     30.00 127.00   1.00    3.00    --  100.00 -61.00  30.00   97
 11  \w     17.00 109.00   1.00    3.00    --  100.00 -94.00-120.00   92
 12  \w     76.00 171.00   1.00    3.00    --  100.00  45.00-120.00   95
 13  \w     26.00 121.00   1.00    3.00    --  100.00-125.00-120.00   95
 14  \w     26.00 121.00   1.00    3.00    --  100.00-125.00  30.00   95
 15  \w     26.00 121.00   1.00    3.00    --  100.00-125.00 120.00   95
 16  \w     26.00 132.00   1.00    3.00    --  100.00 -77.00  30.00  106
 17  \w     73.00 174.00   1.00    3.00    --  100.00 125.00 -60.00  101
 18  \w     26.00 121.00   1.00    3.00    --  100.00-125.00-150.00   95
 19  \w     76.00 171.00   1.00    3.00    --  100.00  45.00 -30.00   95
 20  \w    121.00 171.00   1.00    3.00    --  100.00  45.00 150.00   50
 21  \w    122.00 161.00   1.00    3.00    --  100.00  45.00 -90.00   39
 22  \w     29.00  78.00   1.00    3.00    --  100.00 -77.00-120.00   49
 23  \w     94.00 120.00   1.00    3.00    --  100.00 -77.00-120.00   26
 24  \w     27.00  56.00   1.00    3.00    --  100.00 -30.00  60.00   29
 25  \w     75.00 122.00   1.00    3.00    --  100.00 -30.00  60.00   47
 26  \w    116.00 173.00   1.00    3.00    --  100.00  30.00-150.00   57
 27  \w     59.00  85.00   1.00    3.00    --  100.00 -45.00  60.00   26
 28  \w     76.00 104.00   1.00    3.00    --  100.00  45.00 -90.00   28
 29  \w     33.00  60.00   1.00    3.00    --  100.00-125.00  60.00   27
 30  \w     75.00 120.00   1.00    3.00    --  100.00-125.00-180.00   45
 31  \w     96.00 121.00   1.00    3.00    --  100.00-125.00  60.00   25
 32  \w     53.00 120.00   1.00    3.00    --  100.00-125.00 -30.00   67
 33  \w     76.00 115.00   1.00    3.00    --  100.00 125.00 -30.00   39
 34  \w    129.00 174.00   1.00    3.00    --  100.00 125.00 -30.00   45
 35  \w     77.00 161.00   1.00    3.00    --  100.00  45.00-180.00   84
 36  \w     95.00 144.00   1.00    3.00    --  100.00  30.00   0.00   49
 37  \w     82.00 109.00   1.00    3.00    --  100.00 -94.00   0.00   27
 38  \w     36.00  62.00   1.00    3.00    --  100.00-125.00-180.00   26
 39  \w     91.00 119.00   1.00    3.00    --  100.00 -45.00  60.00   28
 40  \w     64.00  91.00   1.00    3.00    --  100.00 -61.00 -30.00   27
 41  \w     31.00  83.00   1.00    3.00    --  100.00 -94.00 150.00   52
 42  \w     63.00  89.00   1.00    3.00    --  100.00-125.00 -90.00   26
 43  \w     76.00 171.00   1.00    3.00    --  100.00  45.00 -60.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0145489000
_diffrn_orient_matrix_UB_12      0.0797317000
_diffrn_orient_matrix_UB_13      -0.0292294000
_diffrn_orient_matrix_UB_21      -0.1646035000
_diffrn_orient_matrix_UB_22      -0.0131357000
_diffrn_orient_matrix_UB_23      -0.0434105000
_diffrn_orient_matrix_UB_31      -0.0452253000
_diffrn_orient_matrix_UB_32      0.0222771000
_diffrn_orient_matrix_UB_33      0.0789781000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            54304
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.115
_diffrn_reflns_theta_min         2.718
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.413
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.00565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 4636 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.468(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     725
_refine_ls_number_reflns         10869
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.041
_refine_ls_shift/su_mean         0.010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0485P)^2^+0.7208P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0882
_reflns_Friedel_coverage         0.930
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                10130
_reflns_number_total             10869
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc09640b2.cif
_cod_data_source_block           ylm_170503
_cod_depositor_comments
'Adding full bibliography for 7121256--7121258.cif.'
_cod_original_cell_volume        2772.80(3)
_cod_database_code               7121256
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.872
_shelx_estimated_absorpt_t_min   0.677
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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:
 C22(H22), C36(H36), C29(H29), C37(H37)
2.b Secondary CH2 refined with riding coordinates:
 C39(H39A,H39B), C40(H40A,H40B), C65(H65A,H65B), C33(H33A,H33B), C51(H51A,
 H51B), C52(H52A,H52B)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C21(H21), C23(H23), C26(H26), C32(H32), C47(H47), C55(H55),
 C56(H56), C57(H57), C60(H60), C64(H64), C68(H68), C71(H71), C72(H72), C74(H74),
  C75(H75), C15(H15), C25(H25), C28(H28), C30(H30), C38(H38), C42(H42),
 C45(H45), C49(H49), C59(H59), C63(H63), C66(H66), C67(H67), C69(H69), C70(H70),
  C73(H73), C76(H76)
2.d Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C62(H62A,H62B,H62C), C24(H24A,H24B,H24C), C58(H58A,H58B,
 H58C)
;
_shelx_res_checksum              36488
_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 121.568
_oxdiff_exptl_absorpt_empirical_full_min 0.558