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_7121258
_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         'C25 H24 F N3 O2 S'
_chemical_formula_sum            'C25 H24 F N3 O2 S'
_chemical_formula_weight         449.53
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-01-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-02-07 deposited with the CCDC.
2018-02-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.0490(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.94330(10)
_cell_length_b                   19.2152(3)
_cell_length_c                   13.0237(2)
_cell_measurement_reflns_used    21952
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.3220
_cell_measurement_theta_min      2.3100
_cell_volume                     2225.63(5)
_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    'SIR2004 (Burla et al., 2007)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.988
_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     19.00 114.00   1.00    3.00    --   44.52  57.00-120.00   95
  2  \w    -25.00  70.00   1.00    3.00    --   44.52 -57.00  30.00   95
  3  \w    -25.00  70.00   1.00    3.00    --   44.52 -57.00-180.00   95
  4  \w     19.00 114.00   1.00    3.00    --   44.52  57.00 -30.00   95
  5  \w   -164.00 -73.00   1.00   10.00    --  -90.00-125.00-180.00   91
  6  \w   -169.00 -51.00   1.00   10.00    --  -90.00 -15.00   0.00  118
  7  \w     26.00 121.00   1.00   10.00    --  100.00-125.00  60.00   95
  8  \w     17.00 109.00   1.00   10.00    --  100.00 -94.00 -90.00   92
  9  \w     73.00 174.00   1.00   10.00    --  100.00 125.00-180.00  101
 10  \w     73.00 173.00   1.00   10.00    --  100.00  30.00  30.00  100
 11  \w     26.00 132.00   1.00   10.00    --  100.00 -77.00  30.00  106
 12  \w     73.00 174.00   1.00   10.00    --  100.00 125.00-120.00  101
 13  \w     26.00 121.00   1.00   10.00    --  100.00-125.00 120.00   95
 14  \w     73.00 173.00   1.00   10.00    --  100.00  30.00   0.00  100
 15  \w     30.00 127.00   1.00   10.00    --  100.00 -61.00 -90.00   97
 16  \w     17.00 109.00   1.00   10.00    --  100.00 -94.00-150.00   92
 17  \w     26.00 121.00   1.00   10.00    --  100.00-125.00 -90.00   95
 18  \w     26.00 100.00   1.00   10.00    --  100.00 -94.00 120.00   74
 19  \w    108.00 152.00   1.00   10.00    --  100.00 125.00 -90.00   44
 20  \w     81.00 174.00   1.00   10.00    --  100.00  77.00 120.00   93
 21  \w     92.00 165.00   1.00   10.00    --  100.00  61.00  60.00   73
 22  \w     57.00  93.00   1.00   10.00    --  100.00 -15.00  30.00   36
 23  \w     42.00  86.00   1.00   10.00    --  100.00 -94.00-120.00   44
 24  \w     35.00  98.00   1.00   10.00    --  100.00 -61.00  30.00   63
 25  \w     73.00  99.00   1.00   10.00    --  100.00 125.00 -60.00   26
 26  \w     22.00  48.00   1.00   10.00    --  100.00 -15.00  30.00   26
 27  \w    106.00 172.00   1.00   10.00    --  100.00 125.00 -60.00   66
 28  \w     68.00 100.00   1.00   10.00    --  100.00  77.00 -90.00   32
 29  \w     68.00 128.00   1.00   10.00    --  100.00  15.00   0.00   60
 30  \w     41.00  67.00   1.00   10.00    --  100.00 -94.00  33.00   26
 31  \w     74.00 107.00   1.00   10.00    --  100.00 -94.00  33.00   33
 32  \w     60.00 101.00   1.00   10.00    --  100.00 -45.00 150.00   41
 33  \w     28.00  54.00   1.00   10.00    --  100.00 -94.00  90.00   26
 34  \w     34.00  85.00   1.00   10.00    --  100.00 -45.00  60.00   51
 35  \w     96.00 121.00   1.00   10.00    --  100.00-125.00-180.00   25
 36  \w     79.00 120.00   1.00   10.00    --  100.00-125.00 -60.00   41
 37  \w     27.00  81.00   1.00   10.00    --  100.00 -77.00 120.00   54
 38  \w     21.00  47.00   1.00   10.00    --  100.00 -94.00-180.00   26
;
_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      -0.1728177000
_diffrn_orient_matrix_UB_12      -0.0017614000
_diffrn_orient_matrix_UB_13      -0.0048992000
_diffrn_orient_matrix_UB_21      0.0077128000
_diffrn_orient_matrix_UB_22      -0.0744785000
_diffrn_orient_matrix_UB_23      0.0441486000
_diffrn_orient_matrix_UB_31      0.0090236000
_diffrn_orient_matrix_UB_32      0.0297130000
_diffrn_orient_matrix_UB_33      0.1103017000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            33425
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.599
_diffrn_reflns_theta_min         4.116
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.592
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27720
_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    1.342
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0473P)^2^+0.7709P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0953
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4077
_reflns_number_total             4360
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc09640b2.cif
_cod_data_source_block           ylm_171016
_cod_depositor_comments
'Adding full bibliography for 7121256--7121258.cif.'
_cod_database_code               7121258
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.857
_shelx_estimated_absorpt_t_min   0.647
_reflns_odcompleteness_completeness 99.54
_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 Riding coordinates:
 N007(H007)
2.b Ternary CH refined with riding coordinates:
 C00B(H00B)
2.c Secondary CH2 refined with riding coordinates:
 C00I(H00A,H00D), C00L(H00E,H00G)
2.d Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00F(H00F), C00H(H00H), C00J(H00J), C00M(H00M), C00N(H00N),
 C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00T(H00T), C00U(H00U)
2.e Idealised Me refined as rotating group:
 C00V(H00I,H00K,H00L), C00W(H00S,H00V,H00W)
;
_shelx_res_checksum              20785
_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 2.392
_oxdiff_exptl_absorpt_empirical_full_min 0.566