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_7157324
_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_formula_moiety         'C30 H26 O5'
_chemical_formula_sum            'C30 H26 O5'
_chemical_formula_weight         466.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-03-28 deposited with the CCDC.	2020-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.056(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3416(4)
_cell_length_b                   11.0113(3)
_cell_length_c                   14.5008(4)
_cell_measurement_reflns_used    8317
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.9510
_cell_measurement_theta_min      5.0930
_cell_volume                     2211.35(11)
_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 1.000
_diffrn_measured_fraction_theta_max 0.981
_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    -35.00  32.00   1.00    1.00    --  -41.11  57.00  30.00   67
  2  \w     14.00  61.00   1.00    1.00    --   41.11  57.00   0.00   47
  3  \w     87.00 112.00   1.00    1.00    --   41.11  57.00   0.00   25
  4  \w     49.00 129.00   1.00    5.00    --  106.95 -30.00 120.00   80
  5  \w     85.00 146.00   1.00    5.00    --  106.95  30.00  60.00   61
  6  \w     90.00 130.00   1.00    5.00    --  106.95 -45.00-120.00   40
  7  \w     87.00 118.00   1.00    5.00    --  106.95-125.00   0.00   31
  8  \w     78.00 106.00   1.00    5.00    --  106.95 -94.00  60.00   28
  9  \w     41.00  90.00   1.00    5.00    --  106.95 -77.00   0.00   49
 10  \w     38.00 120.00   1.00    5.00    --  106.95 -61.00  30.00   82
 11  \w     37.00  90.00   1.00    1.00    --   41.11-125.00  90.00   53
 12  \w     25.00 156.00   1.00    5.00    --  106.95 -15.00  30.00  131
 13  \w     40.00 118.00   1.00    5.00    --  106.95-125.00-150.00   78
 14  \w     43.00 126.00   1.00    5.00    --  106.95 -30.00-150.00   83
 15  \w     38.00 130.00   1.00    5.00    --  106.95 -77.00-150.00   92
 16  \w    -74.00  30.00   1.00    1.00    --  -41.11  77.00-120.00  104
 17  \w   -116.00 -19.00   1.00    1.00    --  -41.11 -37.00  90.00   97
;
_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      -0.0823585000
_diffrn_orient_matrix_UB_12      -0.0160812000
_diffrn_orient_matrix_UB_13      -0.0915717000
_diffrn_orient_matrix_UB_21      -0.0007348000
_diffrn_orient_matrix_UB_22      -0.1376946000
_diffrn_orient_matrix_UB_23      0.0186508000
_diffrn_orient_matrix_UB_31      -0.0748307000
_diffrn_orient_matrix_UB_32      0.0188878000
_diffrn_orient_matrix_UB_33      0.0580145000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14548
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.679
_diffrn_reflns_theta_min         3.862
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.766
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80181
_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    1.401
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0457
_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^)+(0.0726P)^2^+0.7133P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1268
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3940
_reflns_number_total             4387
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02690h2.cif
_cod_data_source_block           c-18
_cod_depositor_comments
'Adding full bibliography for 7157323--7157327.cif.'
_cod_database_code               7157324
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.920
_shelx_estimated_absorpt_t_min   0.900
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C10(H10), C11(H11), C9(H9), C16(H16), C15(H15), C19(H19), C14(H14), C17(H17),
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C21(H21A,H21B), C13(H13A,H13B), C20(H20A,H20B), C29(H29A,H29B)
2.c Aromatic/amide H refined with riding coordinates:
 C28(H28), C24(H24), C5(H5), C2(H2), C25(H25), C4(H4), C3(H3)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.443
_oxdiff_exptl_absorpt_empirical_full_min 0.710