Palladium-catalyzed post-Ugi arylative dearomatization/Michael addition cascade towards plicamine analogues.
Liu, Chao; Zhao, Ruiqi; Song, Liangliang; Li, Zhenghua; Tian, Guilong; He, Yi; Van Meervelt, Luc; Peshkov, Vsevolod A.; Van der Eycken, Erik V.; Organic & biomolecular chemistry 19 (2021) 9752–9757; doi:10.1039/d1ob01805a

data_7158343
_publ_section_title
;
 Palladium-catalyzed post-Ugi arylative dearomatization/Michael addition
 cascade towards plicamine analogues.
;
_journal_issue                   44
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9752
_journal_page_last               9757
_journal_paper_doi               10.1039/d1ob01805a
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C30 H28 N2 O3'
_chemical_formula_sum            'C30 H28 N2 O3'
_chemical_formula_weight         464.54
_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
_audit_creation_date             2019-11-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-06-08 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                85.493(2)
_cell_angle_beta                 80.059(2)
_cell_angle_gamma                63.776(3)
_cell_formula_units_Z            2
_cell_length_a                   9.1811(2)
_cell_length_b                   9.9659(2)
_cell_length_c                   14.9148(4)
_cell_measurement_reflns_used    18348
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.9890
_cell_measurement_theta_min      3.0280
_cell_volume                     1205.83(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_detector_type            Eos
_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    -94.00 -34.00   1.00    7.50    --  -17.07 178.00 150.00   60
  2  \w    -86.00   4.00   1.00    7.50    --  -17.07 -57.00-150.00   90
  3  \w    -86.00   4.00   1.00    7.50    --  -17.07 -57.00  90.00   90
  4  \w    -38.00  52.00   1.00    7.50    --  -17.07  57.00   0.00   90
  5  \w    -87.00  13.00   1.00    7.50    --  -17.07 -77.00 -30.00  100
  6  \w    -20.00  61.00   1.00    7.50    --   18.87 -99.00  90.00   81
  7  \w    -50.00  40.00   1.00    7.50    --   18.87 -57.00  90.00   90
  8  \w    -20.00  61.00   1.00    7.50    --   18.87 -99.00-180.00   81
  9  \w    -20.00  61.00   1.00    7.50    --   18.87 -99.00 -30.00   81
 10  \w    -54.00  92.00   1.00    7.50    --   18.87   0.00 120.00  146
 11  \w    -20.00  25.00   1.00    7.50    --  -17.07 -99.00-180.00   45
 12  \w    -20.00  25.00   1.00    7.50    --  -17.07 -99.00   0.00   45
 13  \w     -7.00  91.00   1.00    7.50    --   18.87  38.00-150.00   98
 14  \w    -50.00  40.00   1.00    7.50    --   18.87 -57.00 -90.00   90
 15  \w    -54.00  92.00   1.00    7.50    --   18.87   0.00-180.00  146
 16  \w    -54.00  92.00   1.00    7.50    --   18.87   0.00-150.00  146
 17  \w    -54.00  92.00   1.00    7.50    --   18.87   0.00-120.00  146
 18  \w     -4.00  72.00   1.00    7.50    --   18.87-118.00   3.00   76
 19  \w    -54.00  92.00   1.00    7.50    --   18.87   0.00 -60.00  146
 20  \w    -54.00   4.00   1.00    7.50    --   18.87   0.00 -30.00   58
 21  \w    -54.00  92.00   1.00    7.50    --   18.87   0.00 -90.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0539883000
_diffrn_orient_matrix_UB_12      0.0316972000
_diffrn_orient_matrix_UB_13      -0.0326317000
_diffrn_orient_matrix_UB_21      0.0659219000
_diffrn_orient_matrix_UB_22      -0.0372059000
_diffrn_orient_matrix_UB_23      -0.0352848000
_diffrn_orient_matrix_UB_31      -0.0183601000
_diffrn_orient_matrix_UB_32      -0.0624955000
_diffrn_orient_matrix_UB_33      0.0046144000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            49581
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.503
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         4945
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0470
_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^)+(0.0371P)^2^+0.5815P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1204
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4043
_reflns_number_total             4945
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob01805a2.cif
_cod_data_source_block           ev2039
_cod_depositor_comments          'Adding full bibliography for 7158343.cif.'
_cod_database_code               7158343
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C30 H26 N2 O3'
_chemical_oxdiff_usercomment     LLS-1
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.972
_diffrn_oxdiff_ac4_digest_frames
;
01989d065ee0b7f0e0cb118d99f0b8f429000271435
;
_reflns_odcompleteness_completeness 99.96
_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.a Ternary CH refined with riding coordinates:
 C3(H3), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C34(H34A,H34B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C22(H22), C23(H23), C24(H24),
 C25(H25), C26(H26), C28(H28), C29(H29), C30(H30), C31(H31)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.702
_oxdiff_exptl_absorpt_empirical_full_min 0.552