Synthesis of chromone-containing polycyclic compounds via palladium-catalyzed [2 + 2 + 1] annulation.
Li, Mi-Zhuan; Tong, Qi; Han, Wen-Yong; Yang, Si-Yi; Cui, Bao-Dong; Wan, Nan-Wei; Chen, Yong-Zheng; Organic & biomolecular chemistry 18 (2020) 1112–1116; doi:10.1039/c9ob02690h

data_7157323
_publ_section_title
;
 Synthesis of chromone-containing polycyclic compounds via
 palladium-catalyzed [2 + 2 + 1] annulation.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1112
_journal_page_last               1116
_journal_paper_doi               10.1039/c9ob02690h
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C29 H26 O3'
_chemical_formula_sum            'C29 H26 O3'
_chemical_formula_weight         422.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-08 deposited with the CCDC.	2020-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.501(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.1406(8)
_cell_length_b                   12.8442(6)
_cell_length_c                   10.0734(5)
_cell_measurement_reflns_used    3329
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.1650
_cell_measurement_theta_min      4.3900
_cell_volume                     2070.48(18)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.854
_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     -3.00  79.00   1.00    3.01    --   11.74  37.00  90.00   82
  2  \w     -1.00  25.00   1.00    3.01    --  -11.51 -99.00  30.00   26
  3  \w     18.00  62.00   1.00    3.01    --  -11.51  37.00-180.00   44
  4  \w     52.00 100.00   1.00    3.01    --   11.74 178.00  30.00   48
;
_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      0.0162728000
_diffrn_orient_matrix_UB_12      0.0512694000
_diffrn_orient_matrix_UB_13      -0.0003118000
_diffrn_orient_matrix_UB_21      0.0410274000
_diffrn_orient_matrix_UB_22      -0.0202778000
_diffrn_orient_matrix_UB_23      0.0031305000
_diffrn_orient_matrix_UB_31      -0.0041103000
_diffrn_orient_matrix_UB_32      -0.0011835000
_diffrn_orient_matrix_UB_33      -0.0710604000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.854
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5224
_diffrn_reflns_point_group_measured_fraction_full 0.703
_diffrn_reflns_point_group_measured_fraction_max 0.564
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.490
_diffrn_reflns_theta_min         3.772
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78945
_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            colorless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 748 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3244
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0348
_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^)+(0.0470P)^2^+0.7185P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0906
_reflns_Friedel_coverage         0.319
_reflns_Friedel_fraction_full    0.409
_reflns_Friedel_fraction_max     0.273
_reflns_number_gt                3140
_reflns_number_total             3244
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02690h2.cif
_cod_data_source_block           exp_437
_cod_depositor_comments
'Adding full bibliography for 7157323--7157327.cif.'
_cod_database_code               7157323
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.983
_reflns_odcompleteness_completeness 99.64
_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
2.a Ternary CH refined with riding coordinates:
 C13(H13), C16(H16), C12(H12), C11(H11), C18(H18), C20(H20), C10(H10),
 C17(H17), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C19(H19A,H19B), C21(H21A,H21B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C4(H4), C29(H29), C6(H6), C28(H28), C25(H25), C27(H27),
 C26(H26)
;
_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 1.230
_oxdiff_exptl_absorpt_empirical_full_min 0.848