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_7121257
_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 Cl N3 O3 S'
_chemical_formula_sum            'C32 H30 Cl N3 O3 S'
_chemical_formula_weight         572.10
_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                90.0
_cell_angle_beta                 94.876(5)
_cell_angle_gamma                90.0
_cell_formula_units_Z            4
_cell_length_a                   8.6912(5)
_cell_length_b                   27.8849(16)
_cell_length_c                   11.4280(6)
_cell_measurement_reflns_used    9559
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.2480
_cell_measurement_theta_min      3.1550
_cell_volume                     2759.6(3)
_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
_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    -20.00  64.00   1.00    3.00    --   44.52 -37.00-120.00   84
  2  \w     76.00 102.00   1.00   10.00    --  100.00  45.00-150.00   26
  3  \w     75.00 112.00   1.00    3.00    --   44.52 125.00-120.00   37
  4  \w     25.00  56.00   1.00   10.00    --  100.00 -94.00 -30.00   31
  5  \w     57.00 127.00   1.00   10.00    --  100.00 -61.00-150.00   70
  6  \w     75.00 144.00   1.00   10.00    --  100.00  30.00  30.00   69
  7  \w     78.00 117.00   1.00    3.00    --   44.52 125.00 -30.00   39
  8  \w     74.00 100.00   1.00    3.00    --   44.52 125.00 -90.00   26
  9  \w     70.00 158.00   1.00   10.00    --  100.00  77.00  60.00   88
 10  \w     34.00 124.00   1.00   10.00    --  100.00 -77.00 120.00   90
 11  \w    -93.00 -66.00   1.00   10.00    --  -90.00 -61.00 150.00   27
 12  \w   -154.00-118.00   1.00   10.00    --  -90.00 -61.00 150.00   36
 13  \w   -161.00-136.00   1.00   10.00    --  -90.00 -94.00 120.00   25
;
_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      -0.1769111000
_diffrn_orient_matrix_UB_12      0.0060999000
_diffrn_orient_matrix_UB_13      -0.0128632000
_diffrn_orient_matrix_UB_21      0.0169151000
_diffrn_orient_matrix_UB_22      0.0495194000
_diffrn_orient_matrix_UB_23      0.0594157000
_diffrn_orient_matrix_UB_31      0.0103898000
_diffrn_orient_matrix_UB_32      0.0236493000
_diffrn_orient_matrix_UB_33      -0.1208419000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11648
_diffrn_reflns_point_group_measured_fraction_full 0.737
_diffrn_reflns_point_group_measured_fraction_max 0.737
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         3.170
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.252
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51568
_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    1.377
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.13(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     725
_refine_ls_number_reflns         7260
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0983P)^2^+0.2569P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1304
_refine_ls_wR_factor_ref         0.1370
_reflns_Friedel_coverage         0.444
_reflns_Friedel_fraction_full    0.464
_reflns_Friedel_fraction_max     0.464
_reflns_number_gt                6616
_reflns_number_total             7260
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc09640b2.cif
_cod_data_source_block           ylm_r11_160810
_cod_depositor_comments
'Adding full bibliography for 7121256--7121258.cif.'
_cod_original_sg_symbol_H-M      'P 1 21/c 1'
_cod_database_code               7121257
_shelx_shelxl_version_number     2016/6
_cell_oxdiff_angle_alpha         90.044(3)
_cell_oxdiff_angle_beta          94.824(3)
_cell_oxdiff_angle_gamma         90.021(3)
_cell_oxdiff_length_a            8.6846(4)
_cell_oxdiff_length_b            27.9013(9)
_cell_oxdiff_length_c            11.4291(4)
_cell_oxdiff_measurement_reflns_used 9559
_cell_oxdiff_volume              2759.59(18)
_shelx_estimated_absorpt_t_max   0.806
_shelx_estimated_absorpt_t_min   0.551
_reflns_odcompleteness_completeness 99.76
_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:
 C19(H19), C24(H24), C21(H21), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B), C49(H49A,H49B), C54(H54A,H54B), C31(H31A,H31B), C53(H53A,
 H53B), C72(H72A,H72B)
2.c Aromatic/amide H refined with riding coordinates:
 C26(H26), C27(H27), C30(H30), C42(H42), C43(H43), C45(H45), C51(H51),
 C55(H55), C59(H59), C60(H60), C61(H61), C62(H62), C65(H65), C68(H68), C69(H69),
  C75(H75), C25(H25), C28(H28), C38(H38), C40(H40), C41(H41), C44(H44),
 C46(H46), C48(H48), C57(H57), C63(H63), C64(H64), C66(H66), C67(H67), C70(H70),
  C73(H73), C74(H74)
2.d Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C77(H77A,H77B,H77C), C34(H34A,H34B,H34C), C76(H76A,H76B,
 H76C)
;
_shelx_res_checksum              71528
_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 3.223
_oxdiff_exptl_absorpt_empirical_full_min 0.430