N-Heterocyclic carbene-catalyzed [3 + 3] annulation of bromoenals with 2-aminochromones to access chromeno[2,3-<i>b</i>]pyridinones.
Jiang, Pengrui; Guo, Jingcheng; Gong, Minghua; Zhou, Xiangui; Cao, Wei; Fu, Zhenqian; Huang, Wei; Organic & biomolecular chemistry 19 (2021) 4882–4886; doi:10.1039/d1ob00720c

data_7158086
_publ_section_title
;
 N-Heterocyclic carbene-catalyzed [3 + 3] annulation of bromoenals with
 2-aminochromones to access chromeno[2,3-<i>b</i>]pyridinones.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4882
_journal_page_last               4886
_journal_paper_doi               10.1039/d1ob00720c
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C23 H21 N O5'
_chemical_formula_sum            'C23 H21 N O5'
_chemical_formula_weight         391.41
_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   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc27wcq7
_audit_creation_date             2021-05-03
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_audit_update_record
;
2021-05-05 deposited with the CCDC.	2021-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                89.694(6)
_cell_angle_beta                 63.187(8)
_cell_angle_gamma                89.901(5)
_cell_formula_units_Z            2
_cell_length_a                   9.8017(7)
_cell_length_b                   10.5096(6)
_cell_length_c                   10.5266(9)
_cell_measurement_reflns_used    4322
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.5760
_cell_measurement_theta_min      2.8960
_cell_volume                     967.76(14)
_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-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(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    -20.00  33.00   1.00    3.50    --   11.90 -38.00  30.00   53
  2  \w    -56.00 -26.00   1.00    3.50    --   11.90 -77.00 150.00   30
  3  \w    -62.00 -35.00   1.00    1.50    --   11.90 -38.00  30.00   27
  4  \w      2.00  30.00   1.00    1.50    --  -11.27 -99.00-180.00   28
  5  \w    -20.00  52.00   1.00    1.50    --   11.90 -99.00 150.00   72
  6  \w      6.00  86.00   1.00    1.50    --   11.90  38.00  60.00   80
  7  \w    -21.00  80.00   1.00    1.50    --   11.90  77.00 -90.00  101
  8  \w    -34.00  -3.00   1.00    1.50    --  -11.27 -77.00 120.00   31
  9  \w    -17.00   9.00   1.00    1.50    --   11.90 -99.00  60.00   26
;
_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      -0.0700224000
_diffrn_orient_matrix_UB_12      -0.0306841000
_diffrn_orient_matrix_UB_13      0.0444464000
_diffrn_orient_matrix_UB_21      -0.0139508000
_diffrn_orient_matrix_UB_22      -0.0098806000
_diffrn_orient_matrix_UB_23      -0.0597510000
_diffrn_orient_matrix_UB_31      0.0384931000
_diffrn_orient_matrix_UB_32      -0.0593038000
_diffrn_orient_matrix_UB_33      -0.0125968000
_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  0.0257
_diffrn_reflns_av_unetI/netI     0.0326
_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       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9894
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.168
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84747
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3413
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0699
_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^)+(0.1016P)^2^+1.2390P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1832
_refine_ls_wR_factor_ref         0.1939
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2837
_reflns_number_total             3413
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00720c2.cif
_cod_data_source_block           8092
_cod_depositor_comments          'Adding full bibliography for 7158086.cif.'
_cod_original_cell_volume        967.77(13)
_cod_database_code               7158086
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              17258
_olex2_date_sample_data_collection 2021-05-02
_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 1.291
_oxdiff_exptl_absorpt_empirical_full_min 0.596