Rapid access to C2-quaternary 3-methyleneindolines <i>via</i> base-mediated post-Ugi Conia-ene cyclization.
Zhao, Shuang; He, Yi; Gao, Feiyu; Wei, Yue; Zhang, Jiawei; Chen, Mengxiao; Gao, Yunyun; Zhang, Yuan; Liu, Jun-Yan; Guo, Zufeng; Li, Zhenghua; Nie, Shenyou; Chemical communications (Cambridge, England) 59 (2023) 3099–3102; doi:10.1039/d2cc06281j

data_7131277
_publ_section_title
;
 Rapid access to C2-quaternary 3-methyleneindolines <i>via</i>
 base-mediated post-Ugi Conia-ene cyclization.
;
_journal_issue                   21
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3099
_journal_page_last               3102
_journal_paper_doi               10.1039/d2cc06281j
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C28 H26 N4 O2'
_chemical_formula_sum            'C28 H26 N4 O2'
_chemical_formula_weight         450.53
_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     dual
_audit_creation_date             2021-12-02
_audit_creation_method
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_audit_update_record
;
2022-07-22 deposited with the CCDC.	2023-02-14 downloaded from the CCDC.
;
_cell_angle_alpha                68.189(5)
_cell_angle_beta                 80.409(4)
_cell_angle_gamma                67.475(5)
_cell_formula_units_Z            4
_cell_length_a                   12.8991(6)
_cell_length_b                   13.8257(8)
_cell_length_c                   15.8833(9)
_cell_measurement_reflns_used    6782
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.7460
_cell_measurement_theta_min      3.7750
_cell_volume                     2428.2(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.117a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0892
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.853
_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    -34.00  -8.00   1.00   90.00    --  -18.78  57.00 -60.00   26
  2  \w     20.00  50.00   1.00   90.00    --  -18.78  57.00 -60.00   30
  3  \w    -88.00  -5.00   1.00   90.00    --  -18.78 -57.00 150.00   83
  4  \w    -44.00  33.00   1.00   90.00    --  -18.78  77.00  30.00   77
  5  \w    -35.00  11.00   1.00   90.00    --  -18.78 -77.00  60.00   46
  6  \w    -38.00  49.00   1.00   90.00    --  -18.78  57.00 -90.00   87
  7  \w      7.00  32.00   1.00   90.00    --  -18.78  77.00-180.00   25
  8  \w    -14.00  12.00   1.00   90.00    --  -18.78  77.00 -60.00   26
  9  \w    -24.00  11.00   1.00   90.00    --  -18.78 -77.00 -90.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0019044000
_diffrn_orient_matrix_UB_12      -0.0091458000
_diffrn_orient_matrix_UB_13      0.0471404000
_diffrn_orient_matrix_UB_21      -0.0155551000
_diffrn_orient_matrix_UB_22      0.0579805000
_diffrn_orient_matrix_UB_23      -0.0093597000
_diffrn_orient_matrix_UB_31      -0.0574544000
_diffrn_orient_matrix_UB_32      0.0060654000
_diffrn_orient_matrix_UB_33      0.0023838000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.1012
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            21024
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.980
_diffrn_reflns_theta_min         3.345
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.117a (Rigaku Oxford Diffraction, 2021)
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    1.232
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     635
_refine_ls_number_reflns         11001
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1606
_refine_ls_R_factor_gt           0.0747
_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^)+(0.0483P)^2^+0.7483P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1542
_refine_ls_wR_factor_ref         0.1954
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4998
_reflns_number_total             11001
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc06281j2.cif
_cod_data_source_block           20211130-yq-sz-01-14-2
_cod_depositor_comments          'Adding full bibliography for 7131277.cif.'
_cod_database_code               7131277
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C28 H26 N4 O2'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N005(H005), N006(H006), N008(H008), N009(H009), C00M(H00M), C00R(H00R),
 C00S(H00S), C00T(H00T), C00X(H00X), C011(H011), C012(H012), C013(H013),
 C015(H015), C017(H017), C018(H018), C019(H019), C01A(H01A), C01C(H01C),
 C01D(H01D), C01E(H01E), C01F(H01T), C01H(H01H), C01I(H01U), C01K(H01K),
 C01L(H01L), C01M(H01M), C01O(H01Z), C01T(H2), C01V(H3), C01W(H4)
2.b Idealised Me refined as rotating group:
 C01J(H01V,H01W,H01X), C01N(H01Y,H,HA), C01P(H01,HB,HC), C01Q(H01G,H01I,H01J),
 C01S(H01N,H01O,H01P), C01U(H01Q,H01R,H01S)
;
_shelx_res_checksum              62737
_shelx_hkl_checksum              3187
_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 1.190
_oxdiff_exptl_absorpt_empirical_full_min 0.825