Synthesis of spiroindolenine-3,3'-pyrrolo[2,1-<i>b</i>]quinazolinones through gold(I)-catalyzed dearomative cyclization of <i>N</i>-alkynyl quinazolinone-tethered indoles.
Wang, Wang; Zou, Pei-Sen; Pang, Li; Lei, Yao; Huang, Zi-Yi; Chen, Nan-Ying; Mo, Dong-Liang; Pan, Cheng-Xue; Su, Gui-Fa; Organic & biomolecular chemistry 20 (2022) 2069–2074; doi:10.1039/d1ob02492b

data_7158511
_publ_section_title
;
 Synthesis of spiroindolenine-3,3'-pyrrolo[2,1-<i>b</i>]quinazolinones
 through gold(I)-catalyzed dearomative cyclization of <i>N</i>-alkynyl
 quinazolinone-tethered indoles.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2069
_journal_page_last               2074
_journal_paper_doi               10.1039/d1ob02492b
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C20 H14 Br N3 O'
_chemical_formula_sum            'C20 H14 Br N3 O'
_chemical_formula_weight         392.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_audit_update_record
;
2021-10-07 deposited with the CCDC.	2022-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.5352(5)
_cell_length_b                   14.0585(4)
_cell_length_c                   13.9778(5)
_cell_measurement_reflns_used    6642
_cell_measurement_temperature    295.48(10)
_cell_measurement_theta_max      62.5200
_cell_measurement_theta_min      3.1340
_cell_volume                     3838.8(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.48(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_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    -11.00  16.00   0.50    0.40    --    0.62  37.00 -30.00   54
  2  \w    -40.00  -3.00   0.50    0.40    --    0.62 112.00-164.68   74
  3  \w     24.00  78.00   0.50    0.40    --    0.62  37.00 -30.00  108
  4  \w    126.00 156.00   0.50    2.00    --   83.03  81.00  69.00   60
  5  \w     99.00 157.00   0.50    2.00    --   83.03 125.00  90.00  116
  6  \w    -76.00 -50.00   0.50    2.00    --  -81.78 125.00 -60.00   52
  7  \w    -46.00 -20.00   0.50    2.00    --  -81.78  42.00-117.00   52
  8  \w    -42.00  -4.00   0.50    2.00    --  -81.78  37.00 -90.00   76
  9  \w    -27.00  -2.00   0.50    2.00    --  -81.78  19.00   0.00   50
 10  \w     11.00  38.00   0.50    2.00    --   83.03 -37.00   0.00   54
 11  \w     10.00  39.00   0.50    2.00    --   83.03 -37.00 150.00   58
 12  \w   -158.00 -69.00   0.50    2.00    --  -81.78 -42.00  90.00  178
 13  \w   -134.00 -82.00   0.50    2.00    --  -81.78-114.00-132.00  104
;
_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      -0.0039465000
_diffrn_orient_matrix_UB_12      -0.0936074000
_diffrn_orient_matrix_UB_13      0.0571180000
_diffrn_orient_matrix_UB_21      0.0776362000
_diffrn_orient_matrix_UB_22      -0.0141260000
_diffrn_orient_matrix_UB_23      -0.0137890000
_diffrn_orient_matrix_UB_31      0.0134437000
_diffrn_orient_matrix_UB_32      0.0552187000
_diffrn_orient_matrix_UB_33      0.0931831000
_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  0.0514
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10503
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        62.679
_diffrn_reflns_theta_max         62.679
_diffrn_reflns_theta_min         3.874
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.007
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3012
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0606
_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^)+(0.0631P)^2^+5.6653P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1691
_refine_ls_wR_factor_ref         0.1719
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2592
_reflns_number_total             3012
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02492b2.cif
_cod_data_source_block           20210508-sgf-ww-22-1
_cod_depositor_comments          'Adding full bibliography for 7158511.cif.'
_cod_database_code               7158511
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C152 H104 Br8 N32 O8 '
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     58.86
_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 Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C17(H17), C18(H18)
2.c X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              95513
_shelx_fab_checksum              49217
_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 1.864
_oxdiff_exptl_absorpt_empirical_full_min 0.656