Palladium-catalyzed C-H bond activation and decarboxylation for the assembly of indolo[1,2-<i>f</i>]phenanthridine.
Liu, Xiaobing; Ban, Yong-Liang; Liu, Yanjie; Zhuang, Mengdie; Zhou, Yao; Organic & biomolecular chemistry 22 (2024) 9188–9191; doi:10.1039/d4ob01383b

data_7160177
_publ_section_title
;
 Palladium-catalyzed C-H bond activation and decarboxylation for the
 assembly of indolo[1,2-<i>f</i>]phenanthridine.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9188
_journal_page_last               9191
_journal_paper_doi               10.1039/d4ob01383b
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C23 H19 N O3'
_chemical_formula_sum            'C23 H19 N O3'
_chemical_formula_weight         357.39
_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
_audit_block_doi                 10.5517/ccdc.csd.cc25pg2f
_audit_creation_date             2020-07-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-15 deposited with the CCDC.	2024-10-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.796(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5848(15)
_cell_length_b                   8.7233(10)
_cell_length_c                   15.8098(18)
_cell_measurement_reflns_used    2187
_cell_measurement_temperature    300
_cell_measurement_theta_max      28.6160
_cell_measurement_theta_min      3.9940
_cell_volume                     1811.0(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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, 2008)'
_diffrn_ambient_temperature      300
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.838
_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    -28.00  35.00   1.00    5.00    --   15.65 -38.00  90.00   63
  2  \w    -19.00  19.00   1.00    5.00    --   15.65 -99.00 -30.00   38
  3  \w    -49.00 -11.00   1.00    5.00    --   15.65 -57.00  30.00   38
  4  \w     -1.00  81.00   1.00    5.00    --   15.65  57.00-120.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0505907000
_diffrn_orient_matrix_UB_12      -0.0230108000
_diffrn_orient_matrix_UB_13      0.0111377000
_diffrn_orient_matrix_UB_21      -0.0047150000
_diffrn_orient_matrix_UB_22      0.0307658000
_diffrn_orient_matrix_UB_23      -0.0432599000
_diffrn_orient_matrix_UB_31      0.0183026000
_diffrn_orient_matrix_UB_32      0.0716713000
_diffrn_orient_matrix_UB_33      0.0221052000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0679
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.838
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8360
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.246
_diffrn_reflns_theta_min         3.441
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (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    1.311
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4122
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.1262
_refine_ls_R_factor_gt           0.0644
_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^)+(0.0658P)^2^+0.1367P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1626
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2264
_reflns_number_total             4122
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01383b2.cif
_cod_data_source_block           exp_8115
_cod_depositor_comments          'Adding full bibliography for 7160177.cif.'
_cod_database_code               7160177
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.990
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O004-C00R \\sim O004-C14
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 O004, C00R
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 O004, C14
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Others
 Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=1-FVAR(1)
 Sof(C00R)=Sof(H00P)=Sof(H00Q)=Sof(H00R)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C00F(H00F), C00G(H00G), C00H(H00H), C00J(H00J), C00K(H00K),
 C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O)
5.b Idealised Me refined as rotating group:
 C00P(H00A,H00B,H00C), C00Q(H00D,H00E,H00I), C00R(H00P,H00Q,H00R), C14(H14A,
 H14B,H14C)
;
_shelx_res_checksum              70947
_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 1.467
_oxdiff_exptl_absorpt_empirical_full_min 0.629