One-pot formal [3 + 2] annulation of 2-pyridinyl-substituted <i>p</i>-quinone methides and arynes for the synthesis of 3-aryl pyrido[1,2-<i>a</i>]indoles.
Li, Mengfan; Chen, Yan; Tang, Hao; Cheng, Wen; Liao, Benren; Wang, Qingwei; Yi, Weiyin; Organic & biomolecular chemistry 22 (2024) 5618–5628; doi:10.1039/d4ob00684d

data_7159990
_publ_section_title
;
 One-pot formal [3 + 2] annulation of 2-pyridinyl-substituted
 <i>p</i>-quinone methides and arynes for the synthesis of 3-aryl
 pyrido[1,2-<i>a</i>]indoles.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5618
_journal_page_last               5628
_journal_paper_doi               10.1039/d4ob00684d
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C26 H29 N O'
_chemical_formula_sum            'C26 H29 N O'
_chemical_formula_weight         371.50
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2023-09-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-11-07 deposited with the CCDC.	2024-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                88.7920(10)
_cell_angle_beta                 88.7920(10)
_cell_angle_gamma                80.4880(10)
_cell_formula_units_Z            2
_cell_length_a                   9.32650(10)
_cell_length_b                   9.32650(10)
_cell_length_c                   12.2744(2)
_cell_measurement_reflns_used    7808
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      76.1080
_cell_measurement_theta_min      4.7680
_cell_volume                     1052.59(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.49a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.49a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.49a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.960
_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   -116.00 -73.00   0.50    1.03    --  -47.82-125.00-180.00   86
  2  \w    -38.00  15.00   0.50    1.03    --  -47.82  37.00  30.00  106
  3  \w    -22.00   5.00   0.50    1.03    --  -47.82  19.00-180.00   54
  4  \w    -70.00  25.00   0.50    1.03    --  -47.82  77.00-120.00  190
  5  \w   -103.00 -33.00   0.50    1.03    --  -47.82 -57.00 120.00  140
  6  \w    -14.00  25.00   0.50    1.03    --   47.82 -19.00-180.00   78
  7  \w    -20.00  21.00   0.50    1.03    --   47.82 -19.00 150.00   82
  8  \w   -154.00-128.00   0.50    4.11    --  -86.25-125.00 -90.00   52
  9  \w   -158.00 -76.00   0.50    4.11    --  -86.25 -45.00 150.00  164
 10  \w   -158.00 -78.00   0.50    4.11    --  -86.25 -45.00 120.00  160
 11  \w    -51.00 -22.00   0.50    4.11    --  -86.25  45.00 120.00   58
 12  \w   -108.00 -76.00   0.50    4.11    --  -86.25-125.00 -90.00   64
 13  \w   -152.00-127.00   0.50    4.11    --  -86.25 -45.00   0.00   50
 14  \w     34.00 111.00   0.50    4.11    --  106.49-125.00-120.00  154
 15  \w     74.00 100.00   0.50    4.11    --  106.49 -94.00 150.00   52
 16  \w     95.00 176.00   0.50    4.11    --  106.49 125.00-180.00  162
 17  \w     95.00 121.00   0.50    4.11    --  106.49 125.00 120.00   52
 18  \w     36.00 107.00   0.50    4.11    --  106.49-106.00 129.36  142
 19  \w     60.00 111.00   0.50    4.11    --  106.49-125.00 -60.00  102
 20  \w     37.00  64.00   0.50    4.11    --  106.49 -61.00-150.00   54
 21  \w     35.00  61.00   0.50    4.11    --  106.49 -94.00-180.00   52
 22  \w     94.00 176.00   0.50    4.11    --  106.49  45.00 -90.00  164
 23  \w     71.00 111.00   0.50    4.11    --  106.49-125.00 120.00   80
 24  \w     37.00  62.00   0.50    4.11    --  106.49 -61.00 150.00   50
 25  \w    139.00 177.00   0.50    4.11    --  106.49 125.00 120.00   76
 26  \w     36.00  61.00   0.50    4.11    --  106.49 -94.00 150.00   50
 27  \w     42.00  67.00   0.50    4.11    --  106.49-125.00 120.00   50
 28  \w    147.00 173.00   0.50    4.11    --  106.49  45.00   0.00   52
 29  \w     37.00  63.00   0.50    4.11    --  106.49 -61.00 -60.00   52
 30  \w     40.00 103.00   0.50    4.11    --  106.49 -94.00 -30.00  126
 31  \w     94.00 142.00   0.50    4.11    --  106.49  15.00  60.00   96
 32  \w     98.00 157.00   0.50    4.11    --  106.49  30.00 -30.00  118
 33  \w     96.00 146.00   0.50    4.11    --  106.49  45.00   0.00  100
 34  \w     80.00 111.00   0.50    4.11    --  106.49-125.00 -90.00   62
 35  \w    149.00 174.00   0.50    4.11    --  106.49  15.00  60.00   50
 36  \w     37.00  71.00   0.50    4.11    --  106.49-125.00 -90.00   68
 37  \w     46.00  71.00   0.50    4.11    --  106.49 -94.00  30.00   50
 38  \w     80.00 105.00   0.50    4.11    --  106.49 -94.00  30.00   50
 39  \w     79.00 107.00   0.50    4.11    --  106.49-105.00 -57.05   56
 40  \w     67.00  92.00   0.50    4.11    --  106.49 -94.00 120.00   50
 41  \w     40.00  76.00   0.50    4.11    --  106.49-105.00 -57.05   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0633941000
_diffrn_orient_matrix_UB_12      -0.0647828000
_diffrn_orient_matrix_UB_13      -0.0813919000
_diffrn_orient_matrix_UB_21      -0.0677175000
_diffrn_orient_matrix_UB_22      -0.0273059000
_diffrn_orient_matrix_UB_23      0.0920379000
_diffrn_orient_matrix_UB_31      -0.0558010000
_diffrn_orient_matrix_UB_32      0.1067677000
_diffrn_orient_matrix_UB_33      -0.0258414000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13150
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.529
_diffrn_reflns_theta_min         3.602
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.538
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.49a (Rigaku Oxford Diffraction, 2019)
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    1.172
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0034(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         4256
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0505
_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^)+(0.0802P)^2^+0.2449P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1524
_refine_ls_wR_factor_ref         0.1603
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3642
_reflns_number_total             4256
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00684d2.cif
_cod_data_source_block           cy-2
_cod_depositor_comments          'Adding full bibliography for 7159990.cif.'
_cod_database_code               7159990
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H1-H8B
 2 with sigma of 0.02
 H9B-H1 \\sim H1-H8B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(N1) \\sim Ueq, Uanis(C17) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 N1, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Riding coordinates:
 O1(H1)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C13(H13), C14(H14), C15(H15), C16(H16), C19(H19), C20(H20),
 C21(H21), C22(H22)
5.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C24(H24A,H24B,H24C),
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              19901
_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 1.327
_oxdiff_exptl_absorpt_empirical_full_min 0.723