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_7124439
_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_absolute_configuration ad
_chemical_formula_moiety         'C26 H15 Cl F3 N O6, C H2 Cl2'
_chemical_formula_sum            'C27 H17 Cl3 F3 N O6'
_chemical_formula_weight         614.77
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-01-21
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9362(5)
_cell_length_b                   16.8867(11)
_cell_length_c                   21.0716(11)
_cell_measurement_reflns_used    2592
_cell_measurement_temperature    110.60(14)
_cell_measurement_theta_max      27.0440
_cell_measurement_theta_min      3.5100
_cell_volume                     2468.1(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)/Bruker'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.60(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9966
_diffrn_measured_fraction_theta_max 0.8469
_diffrn_measurement_details
;
  1 omega  -21.00   47.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  -99.0000  -60.0000 68

  2 omega   -2.00   28.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2647   37.0000 -180.0000 30

  3 omega  -72.00  -15.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2647  -57.0000 -180.0000 57

  4 omega   37.00   71.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  178.0000  120.0000 34

  5 omega   53.00   79.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       18.4210  178.0000 -150.0000 26

  6 omega   45.00   80.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       18.4210   19.0000   30.0000 35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0405391000
_diffrn_orient_matrix_UB_12      -0.0238416000
_diffrn_orient_matrix_UB_13      -0.0242880000
_diffrn_orient_matrix_UB_21      0.0069698000
_diffrn_orient_matrix_UB_22      0.0321744000
_diffrn_orient_matrix_UB_23      -0.0214957000
_diffrn_orient_matrix_UB_31      0.0936361000
_diffrn_orient_matrix_UB_32      -0.0127147000
_diffrn_orient_matrix_UB_33      -0.0089151000
_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  0.0441
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12224
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.09
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.442
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90703
_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    1.654
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         4844
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0518
_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^)+(0.0589P)^2^+1.2275P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1266
_reflns_number_gt                4182
_reflns_number_total             4844
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9cc05233j2.cif
_cod_data_source_block           exp_5804
_cod_database_code               7124439
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32