2-Indolymethanols as 4-atom-synthons in oxa-Michael reaction cascade: access to tetracyclic indoles.
Han, Tian-Jiao; Wang, Min-Can; Mei, Guang-Jian; Chemical communications (Cambridge, England) 57 (2021) 8921–8924; doi:10.1039/d1cc03653j

data_7128745
_publ_section_title
;
 2-Indolymethanols as 4-atom-synthons in oxa-Michael reaction cascade:
 access to tetracyclic indoles.
;
_journal_issue                   71
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              8921
_journal_page_last               8924
_journal_paper_doi               10.1039/d1cc03653j
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C22 H19 N O3'
_chemical_formula_sum            'C22 H19 N O3'
_chemical_formula_weight         345.38
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2021-04-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-04-25 deposited with the CCDC.	2021-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.7923(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.34646(16)
_cell_length_b                   28.3786(5)
_cell_length_c                   8.67019(14)
_cell_measurement_reflns_used    3721
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.1510
_cell_measurement_theta_min      5.3110
_cell_volume                     2046.45(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -102.00 -25.00   1.00    3.50    --  -33.50 -57.00 120.00   77
  2  \w    -50.00 -24.00   1.00    3.50    --  -33.50  57.00 -30.00   26
  3  \w   -104.00 -79.00   1.00    3.50    --  -33.50 -37.00 -30.00   25
  4  \w    -69.00 -15.00   1.00    3.50    --  -33.50 -57.00-150.00   54
  5  \w    -15.00  11.00   1.00    3.50    --  -33.50  57.00 -30.00   26
  6  \w    -64.00 -37.00   1.00    3.50    --  -33.50 -19.00-120.00   27
  7  \w     34.00  77.00   1.00    3.50    --   36.47 -99.00-180.00   43
  8  \w     58.00 110.00   1.00    3.50    --   36.47 178.00  60.00   52
  9  \w    -34.00  51.00   1.00    3.50    --   36.47 -37.00-150.00   85
 10  \w     66.00 106.00   1.00    3.50    --   36.47 178.00-120.00   40
 11  \w     47.00  73.00   1.00    3.50    --   36.47  19.00-120.00   26
 12  \w    -22.00  55.00   1.00    3.50    --   36.47 -57.00 150.00   77
 13  \w     -1.00  26.00   1.00    3.50    --   36.47  19.00-120.00   27
 14  \w     66.00 104.00   1.00    3.50    --   36.47  57.00-120.00   38
 15  \w      9.00  78.00   1.00    3.50    --   36.47-106.00  60.00   69
 16  \w     16.00  74.00   1.00    3.50    --   36.47 -19.00   0.00   58
 17  \w    -36.00   5.00   1.00    3.50    --   36.47 -19.00   0.00   41
 18  \w     39.00 117.00   1.00   10.00    --  108.00 -45.00  90.00   78
 19  \w     79.00 178.00   1.00   10.00    --  108.00  15.00-120.00   99
 20  \w     41.00 106.00   1.00   10.00    --  108.00-111.00 120.00   65
 21  \w     37.00 131.00   1.00   10.00    --  108.00 -30.00 -60.00   94
 22  \w     90.00 168.00   1.00   10.00    --  108.00  61.00 -60.00   78
 23  \w    153.00 178.00   1.00   10.00    --  108.00 111.00-120.00   25
 24  \w    153.00 178.00   1.00   10.00    --  108.00 111.00 -60.00   25
 25  \w     87.00 112.00   1.00   10.00    --  108.00-111.00   0.00   25
 26  \w    140.00 175.00   1.00   10.00    --  108.00  61.00  60.00   35
 27  \w    103.00 129.00   1.00   10.00    --  108.00  61.00  60.00   26
 28  \w     53.00 116.00   1.00   10.00    --  108.00 -45.00 150.00   63
 29  \w     39.00 136.00   1.00   10.00    --  108.00 -77.00 -60.00   97
 30  \w     45.00  80.00   1.00   10.00    --  108.00 -94.00 -60.00   35
 31  \w    121.00 157.00   1.00   10.00    --  108.00  30.00 -90.00   36
 32  \w     61.00 109.00   1.00   10.00    --  108.00 -94.00-150.00   48
 33  \w    101.00 147.00   1.00   10.00    --  108.00 111.00-120.00   46
 34  \w     42.00  93.00   1.00   10.00    --  108.00 -15.00-120.00   51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0406308000
_diffrn_orient_matrix_UB_12      0.0181667000
_diffrn_orient_matrix_UB_13      0.1596301000
_diffrn_orient_matrix_UB_21      0.0345528000
_diffrn_orient_matrix_UB_22      -0.0492757000
_diffrn_orient_matrix_UB_23      0.0695743000
_diffrn_orient_matrix_UB_31      0.1773359000
_diffrn_orient_matrix_UB_32      0.0137509000
_diffrn_orient_matrix_UB_33      0.0384706000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14602
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.024
_diffrn_reflns_theta_max         67.024
_diffrn_reflns_theta_min         5.318
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.601
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.121
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3649
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0493
_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^)+(0.0977P)^2^+0.0140P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1455
_refine_ls_wR_factor_ref         0.1591
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2743
_reflns_number_total             3649
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc03653j2.cif
_cod_data_source_block           202104102
_cod_depositor_comments
'Adding full bibliography for 7128745--7128746.cif.'
_cod_database_code               7128745
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O5N2
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.910
_reflns_odcompleteness_completeness 99.95
_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:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C19(H19), C20(H20), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              61534
_shelx_hkl_checksum              13168
_shelx_fab_checksum              94524
_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 2.352
_oxdiff_exptl_absorpt_empirical_full_min 0.808