Dearomative cyclization of pyridines/isoquinolines with cyclopropenones: access to indolizinones and benzo-fused indolizinones.
Liu, Xiang; Shi, Xiaotian; Zhou, Jinlei; Huang, Changfeng; Lin, Yu; Zhang, Chen; Cao, Hua; Chemical communications (Cambridge, England) 59 (2023) 4051–4054; doi:10.1039/d3cc00492a

data_7131402
_publ_section_title
;
 Dearomative cyclization of pyridines/isoquinolines with cyclopropenones:
 access to indolizinones and benzo-fused indolizinones.
;
_journal_issue                   27
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4051
_journal_page_last               4054
_journal_paper_doi               10.1039/d3cc00492a
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C30 H22 Br N O3'
_chemical_formula_sum            'C30 H22 Br N O3'
_chemical_formula_weight         524.39
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-12-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-12-17 deposited with the CCDC.	2023-03-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.388(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5059(4)
_cell_length_b                   10.6245(4)
_cell_length_c                   24.3428(16)
_cell_measurement_reflns_used    4236
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      72.7610
_cell_measurement_theta_min      3.6680
_cell_volume                     2418.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_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    -51.00 -18.00   1.00    1.00    --  -40.73 -38.00  60.00   33
  2  \w    -64.00  33.00   1.00    1.00    --  -40.73  38.00 120.00   97
  3  \w     45.00  82.00   1.00    1.00    --   40.73 -99.00  30.00   37
  4  \w     39.00 127.00   1.00    1.50    --  106.95 -45.00 -90.00   88
  5  \w     93.00 170.00   1.00    1.50    --  106.95  45.00  60.00   77
  6  \w    142.00 178.00   1.00    1.50    --  106.95  30.00  90.00   36
  7  \w    100.00 169.00   1.00    1.50    --  106.95 125.00 -90.00   69
  8  \w     53.00 128.00   1.00    1.50    --  106.95 -77.00   0.00   75
  9  \w     36.00 105.00   1.00    1.50    --  106.95 -95.00-120.00   69
 10  \w   -112.00 -21.00   1.00    1.00    --  -40.73 -57.00 -30.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0379162000
_diffrn_orient_matrix_UB_12      -0.0421473000
_diffrn_orient_matrix_UB_13      -0.0561445000
_diffrn_orient_matrix_UB_21      -0.1507711000
_diffrn_orient_matrix_UB_22      0.0376334000
_diffrn_orient_matrix_UB_23      -0.0300383000
_diffrn_orient_matrix_UB_31      0.0544783000
_diffrn_orient_matrix_UB_32      0.1335423000
_diffrn_orient_matrix_UB_33      -0.0092046000
_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  0.0495
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8406
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.589
_diffrn_reflns_theta_max         66.589
_diffrn_reflns_theta_min         3.692
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.580
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.18224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.285
_refine_diff_density_min         -0.888
_refine_diff_density_rms         0.143
_refine_ls_extinction_coef       0.00150(9)
_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   1.165
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4271
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      5.600
_refine_ls_R_factor_all          0.1331
_refine_ls_R_factor_gt           0.1253
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0487P)^2^+42.1420P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2837
_refine_ls_wR_factor_ref         0.2876
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3794
_reflns_number_total             4271
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc00492a2.cif
_cod_data_source_block           2-297
_cod_depositor_comments          'Adding full bibliography for 7131402.cif.'
_cod_database_code               7131402
_shelx_shelxl_version_number     2018/3
_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
2. Restrained distances
 Br1-C24 \\sim Br2-C24
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Br2) \\sim Ueq: with sigma of 0.00002 and sigma for terminal atoms of
0.00004
4. Rigid body (RIGU) restrains
 Br2, C24
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
5. Others
 Sof(Br2)=1-FVAR(1)
 Sof(Br1)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C22(H22), C23(H23), C25(H25), C26(H26), C27(H27),
  C28(H28), C29(H29), C30(H30)
6.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              61654
_shelx_hkl_checksum              73105
_shelx_fab_checksum              60077
_olex2_date_sample_data_collection 2021-12-04
_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 2.268
_oxdiff_exptl_absorpt_empirical_full_min 0.412