C4-arylation and domino C4-arylation/3,2-carbonyl migration of indoles by tuning Pd catalytic modes: Pd(i)–Pd(ii) catalysis vs. Pd(ii) catalysis
Cheng, Yaohang; Yu, Shijie; He, Yuhang; An, Guanghui; Li, Guangming; Yang, Zhenyu; Chemical Science 12 (2021) 3216–3225; doi:10.1039/D0SC05409G

data_1559981
_publ_section_title
;
 C4-arylation and domino C4-arylation/3,2-carbonyl migration of indoles by
 tuning Pd catalytic modes: Pd(i)--Pd(ii) catalysis vs. Pd(ii) catalysis
;
_journal_issue                   9
_journal_name_full               'Chemical Science'
_journal_page_first              3216
_journal_page_last               3225
_journal_paper_doi               10.1039/D0SC05409G
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety         'C18 H15 N O3'
_chemical_formula_sum            'C18 H15 N O3'
_chemical_formula_weight         586.62
_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     direct
_audit_creation_date             2017-08-06
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Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
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_audit_update_record
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2020-09-10 deposited with the CCDC.	2021-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                96.901(8)
_cell_angle_beta                 107.557(9)
_cell_angle_gamma                92.751(8)
_cell_formula_units_Z            2
_cell_length_a                   8.1516(8)
_cell_length_b                   8.1871(8)
_cell_length_c                   11.8093(11)
_cell_measurement_reflns_used    1512
_cell_measurement_temperature    293(2)
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_cell_measurement_theta_min      3.3060
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1954
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   46.00   80.00   1.0000    5.3100
omega____ theta____ kappa____ phi______ frames
    -       25.5830  178.0000 -150.0000 34

  2 omega  -24.00   55.00   1.0000    5.3100
omega____ theta____ kappa____ phi______ frames
    -       25.5830  -99.0000   60.0000 79

  3 omega   75.00  102.00   1.0000    5.3100
omega____ theta____ kappa____ phi______ frames
    -       25.5830   38.0000  120.0000 27

  4 omega -100.00   -8.00   1.0000    5.3100
omega____ theta____ kappa____ phi______ frames
    -      -26.8330  -57.0000 -180.0000 92

  5 omega    9.00   48.00   1.0000    5.3100
omega____ theta____ kappa____ phi______ frames
    -      -26.8330   77.0000   60.0000 39

  6 omega  -25.00   20.00   1.0000    5.3100
omega____ theta____ kappa____ phi______ frames
    -      -26.8330  -99.0000  120.0000 45

  7 omega  -56.00   37.00   1.0000    5.3100
omega____ theta____ kappa____ phi______ frames
    -      -26.8330   57.0000  -30.0000 93

  8 omega  -12.00   13.00   1.0000    5.3100
omega____ theta____ kappa____ phi______ frames
    -      -26.8330  -99.0000  -60.0000 25
;
_diffrn_measurement_device_type  MoK\a
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_diffrn_orient_matrix_UB_21      -0.0143982000
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_diffrn_orient_matrix_UB_31      0.0888375000
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_diffrn_orient_matrix_UB_33      0.0043806000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4629
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.313
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
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             308
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
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_refine_diff_density_min         -0.235
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_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.702
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2615
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.702
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0453
_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^)+(0.1310P)^2^+0.4060P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1532
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2012
_reflns_number_total             2615
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc05409g2.cif
_cod_data_source_block           20170803agh
_cod_depositor_comments
;
Adding full bibliography for 1559980--1559981.cif.

2022-06-21
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C12 H10 N0.67 O2'
_cod_original_formula_weight         195.54
_cod_original_formula_moiety         '0.67(C18 H15 N O3)'
_cod_original_formula_units_Z            3
_cod_original_cell_volume        743.02(13)
_cod_database_code               1559981
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.981
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C8(H8), C13(H13), C16(H16), C18(H18), C19(H19),
 C20(H20)
2.b Idealised Me refined as rotating group:
 C0AA(H0AA,H0AB,H0AC), C1AA(H1AA,H1AB,H1AC)
;
_shelx_res_checksum              91868
_olex2_submission_special_instructions 'No special instructions were received'