Palladium-catalysed enol/enolate directed oxidative annulation: functionalized naphthofuroquinones synthesis and bioactivity evaluation
Wang, Lei; Lv, Shuaipeng; Liu, Haitao; Kang, Jie; Luo, Yun; Gong, Ting; Dong, Zhengqi; Sun, Guibo; He, Chun-nian; Sun, Xiaobo; Chemical Communications  (2019) –; doi:10.1039/C9CC05233J

data_7124437
_publ_section_title
;
 Palladium-catalysed enol/enolate directed oxidative annulation:
 functionalized naphthofuroquinones synthesis and bioactivity evaluation
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC05233J
_journal_year                    2019
_chemical_formula_moiety         'C24 H14 O3'
_chemical_formula_sum            'C24 H14 O3'
_chemical_formula_weight         350.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-04-02
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_audit_update_record
;
2019-04-13 deposited with the CCDC.	2019-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.807(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.2754(16)
_cell_length_b                   13.4235(13)
_cell_length_c                   9.5478(9)
_cell_measurement_reflns_used    1267
_cell_measurement_temperature    108.00(14)
_cell_measurement_theta_max      28.5150
_cell_measurement_theta_min      3.9580
_cell_volume                     1697.7(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'A short history of SHELX (Sheldrick, 2007)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      108.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.8401
_diffrn_measurement_details
;
  1 omega  -25.00    0.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4210  -99.0000  -30.0000 25

  2 omega   -1.00   26.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4210  -99.0000 -150.0000 27

  3 omega   -1.00   86.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772   37.0000    0.0000 87

  4 omega   33.00   81.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772   77.0000   30.0000 48

  5 omega   66.00   91.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  178.0000  -90.0000 25

  6 omega  -23.00   11.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4210  -99.0000   90.0000 34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0528358000
_diffrn_orient_matrix_UB_12      0.0079562000
_diffrn_orient_matrix_UB_13      0.0012008000
_diffrn_orient_matrix_UB_21      -0.0038231000
_diffrn_orient_matrix_UB_22      0.0366218000
_diffrn_orient_matrix_UB_23      0.0529051000
_diffrn_orient_matrix_UB_31      0.0075482000
_diffrn_orient_matrix_UB_32      -0.0372039000
_diffrn_orient_matrix_UB_33      0.0523520000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0710
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7974
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.97
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3343
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0530
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0319P)^2^+0.1337P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1104
_reflns_number_gt                2354
_reflns_number_total             3343
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9cc05233j2.cif
_cod_data_source_block           exp_5907
_cod_database_code               7124437
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32