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_7157327
_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         'C25 H26 O4'
_chemical_formula_sum            'C25 H26 O4'
_chemical_formula_weight         390.46
_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     direct
_audit_creation_date             2018-11-06
_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                89.6453(18)
_cell_angle_beta                 89.8577(16)
_cell_angle_gamma                83.5587(15)
_cell_formula_units_Z            8
_cell_length_a                   6.28259(10)
_cell_length_b                   18.0959(3)
_cell_length_c                   34.9828(9)
_cell_measurement_reflns_used    21924
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.0950
_cell_measurement_theta_min      2.0890
_cell_volume                     3951.98(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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5368
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -87.00 -38.00   1.00    4.00    --  -11.59 153.00-138.57   49
  2  \w    -87.00 -38.00   1.00    4.00    --  -11.59 153.00 135.25   49
  3  \w    -21.00  88.00   1.00    4.00    --   11.74  77.00 -30.00  109
  4  \w    -20.00  53.00   1.00    4.00    --   11.74 -99.00-180.00   73
  5  \w    -60.00  40.00   1.00    4.00    --   11.74 -57.00  60.00  100
  6  \w    -29.00  92.00   1.00    4.00    --   11.74  19.00 150.00  121
  7  \w     34.00  99.00   1.00    4.00    --   11.74-178.00  90.00   65
  8  \w    -13.00  86.00   1.00    4.00    --   11.74  37.00-120.00   99
  9  \w    -68.00 -23.00   1.00    4.00    --  -11.59 125.00  56.47   45
 10  \w    -66.00 -21.00   1.00    4.00    --  -11.59 122.00 -12.66   45
 11  \w    -69.00 -25.00   1.00    4.00    --  -11.59 127.00 -83.35   44
 12  \w    -85.00 -37.00   1.00    4.00    --  -11.59 151.00 101.58   48
 13  \w    -85.00 -42.00   1.00    4.00    --  -11.59 151.00-168.90   43
 14  \w    -13.00  86.00   1.00    4.00    --   11.74  37.00  30.00   99
;
_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      0.0022700000
_diffrn_orient_matrix_UB_12      0.0117208000
_diffrn_orient_matrix_UB_13      0.0192915000
_diffrn_orient_matrix_UB_21      0.0574993000
_diffrn_orient_matrix_UB_22      -0.0345923000
_diffrn_orient_matrix_UB_23      0.0051591000
_diffrn_orient_matrix_UB_31      0.0979667000
_diffrn_orient_matrix_UB_32      0.0149000000
_diffrn_orient_matrix_UB_33      -0.0035172000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1317
_diffrn_reflns_av_unetI/netI     0.0724
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            90171
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.076
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.702
_refine_diff_density_min         -0.738
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1049
_refine_ls_number_reflns         13935
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0744
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0619P)^2^+71.7043P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1964
_refine_ls_wR_factor_ref         0.2047
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10967
_reflns_number_total             13935
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02690h2.cif
_cod_data_source_block           exp_1049
_cod_depositor_comments
'Adding full bibliography for 7157323--7157327.cif.'
_cod_database_code               7157327
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.987
_reflns_odcompleteness_completeness 99.95
_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. Rigid bond restraints
 C02L, C02X
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C02L \\sim C02X: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
4.a Ternary CH refined with riding coordinates:
 C10(H10), C12(H12), C00S(H00S), C00T(H00T), C17(H17), C13(H13), C15(H15),
 C011(H011), C014(H014), C21(H21), C16(H16), C18(H18), C01G(H01G), C11(H11),
 C01I(H01I), C01K(H01K), C01M(H01M), C01Q(H01Q), C01T(H01T), C01V(H01V),
 C01X(H01X), C01Y(H01Y), C01Z(H01Z), C021(H021), C022(H022), C025(H025),
 C027(H027), C02D(H02G), C02E(H02Z), C02R(H1AA), C02V(H5AA), C02X(H6AA),
 C02Y(H7AA), C02Z(H8AA), C034(H034), C037(H037)
4.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C01O(H01A,H01C), C14(H14A,H14B), C19(H19A,H19B), C020(H02A,
 H02B), C023(H02C,H02D), C22(H22A,H22B), C028(H02O,H02P), C20(H20A,H20B),
 C02A(H02Q,H02R), C02B(H02E,H02F), C02F(H02H,H02I), C02G(H02S,H02T), C02H(H02U,
 H02V), C02M(H0AA,H), C02T(H3AA,HB), C02W(H02M,H02N), C030(H03A,H03B),
 C031(H03C,H03D), C036(H03E,H03F)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C00V(H00V), C2(H2), C01B(H01B), C01E(H01E), C01F(H01F),
 C01N(H01N), C01R(H01R), C3(H3), C026(H026), C02J(H02), C02K(H02W), C02S(H2AA),
 C033(H033), C038(H038)
4.d Idealised Me refined as rotating group:
 C02N(H02J,H02K,H02L), C02O(H02X,H02Y,HA), C25(H25A,H25B,H25C), C02U(H4AA,HC,HD)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
;
_oxdiff_exptl_absorpt_empirical_full_max 1.327
_oxdiff_exptl_absorpt_empirical_full_min 0.700