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_7157326
_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         'C35 H30 O3'
_chemical_formula_sum            'C35 H30 O3'
_chemical_formula_weight         498.59
_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_creation_date             2017-11-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-08-08 deposited with the CCDC.	2020-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                92.252(3)
_cell_angle_beta                 102.556(3)
_cell_angle_gamma                100.001(3)
_cell_formula_units_Z            4
_cell_length_a                   11.8871(3)
_cell_length_b                   12.0988(4)
_cell_length_c                   18.3739(7)
_cell_measurement_reflns_used    8792
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.1320
_cell_measurement_theta_min      3.6070
_cell_volume                     2531.96(15)
_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 0.998
_diffrn_measured_fraction_theta_max 0.844
_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     -9.00  34.00   1.00    5.00    --   11.74  37.00   0.00   43
  2  \w     48.00  85.00   1.00    5.00    --   11.74  37.00   0.00   37
  3  \w     -5.00  68.00   1.00    5.00    --   11.74  37.00-120.00   73
  4  \w    -14.00  28.00   1.00    5.00    --  -11.59 -99.00 -90.00   42
  5  \w    -26.00  32.00   1.00    5.00    --   11.74 -19.00-180.00   58
  6  \w    -56.00  13.00   1.00    5.00    --  -11.59 -37.00 -30.00   69
  7  \w    -42.00  14.00   1.00    5.00    --   11.74 -57.00 120.00   56
;
_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      0.0112639000
_diffrn_orient_matrix_UB_12      0.0581780000
_diffrn_orient_matrix_UB_13      -0.0056330000
_diffrn_orient_matrix_UB_21      0.0268761000
_diffrn_orient_matrix_UB_22      0.0123901000
_diffrn_orient_matrix_UB_23      0.0385599000
_diffrn_orient_matrix_UB_31      0.0549823000
_diffrn_orient_matrix_UB_32      -0.0053475000
_diffrn_orient_matrix_UB_33      -0.0074625000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25396
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.570
_diffrn_reflns_theta_min         3.134
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58372
_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    1.308
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     685
_refine_ls_number_reflns         11996
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0553
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0580P)^2^+1.0328P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1389
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9232
_reflns_number_total             11996
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02690h2.cif
_cod_data_source_block           exp_943
_cod_depositor_comments
'Adding full bibliography for 7157323--7157327.cif.'
_cod_database_code               7157326
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.81
_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:
 C28(H28), C25(H25), C14(H14), C24(H24), C00U(H00U), C00X(H00X), C26(H26),
 C34(H34), C29(H29), C015(H015), C01B(H01B), C01D(H01D), C31(H31), C30(H30),
 C01M(H01M), C01P(H01P), C01R(H01R), C01U(H01U)
2.b Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B), C01T(H01E,H01F), C27(H27A,H27B), C01Z(H01G,H01H), C33(H33A,
 H33B), C022(H02A,H02B), C32(H32A,H32B), C024(H02C,H02D)
2.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C5(H5), C19(H19), C21(H21), C00W(H00W), C12(H12), C011(H011),
 C6(H6), C013(H013), C8(H8), C017(H017), C019(H019), C01A(H01A), C01C(H01C),
 C20(H20), C01I(H01I), C01J(H01J), C3(H3), C01N(H01N), C9(H9), C10(H10), C2(H2),
  C01V(H01V), C11(H11), C01X(H01X), C021(H021)
;
_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 1.706
_oxdiff_exptl_absorpt_empirical_full_min 0.548