Regiocontrol in the oxidative Heck reaction of indole by ligand-enabled switch of the regioselectivity-determining step
Wang, Yu-Jie; Yuan, Chen-Hui; Chu, De-Zhao; Jiao, Lei; Chemical Science  (2020) –; doi:10.1039/D0SC02246B

data_1559171
_publ_section_title
;
 Regiocontrol in the oxidative Heck reaction of indole by ligand-enabled
 switch of the regioselectivity-determining step
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02246B
_journal_year                    2020
_chemical_formula_moiety         'C34 H33 Cl N P Pd, 2(C H2 Cl2)'
_chemical_formula_sum            'C36 H37 Cl5 N P Pd'
_chemical_formula_weight         798.28
_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     dual
_audit_creation_date             2020-01-16
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2020-01-17 deposited with the CCDC.	2020-09-14 downloaded from the CCDC.
;
_cell_angle_alpha                92.906(3)
_cell_angle_beta                 104.074(3)
_cell_angle_gamma                111.149(3)
_cell_formula_units_Z            2
_cell_length_a                   10.4499(4)
_cell_length_b                   11.5254(4)
_cell_length_c                   15.9550(5)
_cell_measurement_reflns_used    6663
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      70.2610
_cell_measurement_theta_min      4.6760
_cell_volume                     1717.91(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.968
_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    -86.00  -5.00   1.00    1.00    --  -40.81 125.00-120.00   81
  2  \w   -107.00  -9.00   1.00    1.00    --  -40.81 -77.00 150.00   98
  3  \w   -111.00 -18.00   1.00    1.00    --  -40.81 -57.00  30.00   93
  4  \w      1.00  32.00   1.00    1.00    --   40.81 -99.00 -90.00   31
  5  \w     16.00  52.00   1.00    2.00    --   98.72 -95.00  90.00   36
  6  \w    141.00 168.00   1.00    2.00    --   98.72 125.00-180.00   27
  7  \w     27.00  93.00   1.00    2.00    --   98.72 -45.00  90.00   66
  8  \w     89.00 170.00   1.00    2.00    --   98.72  30.00-150.00   81
  9  \w     25.00 131.00   1.00    2.00    --   98.72 -77.00-150.00  106
 10  \w     17.00  94.00   1.00    2.00    --   98.72 -95.00 120.00   77
 11  \w     79.00 172.00   1.00    2.00    --   98.72  45.00 -60.00   93
 12  \w     71.00 115.00   1.00    2.00    --   98.72-125.00-120.00   44
 13  \w     39.00 124.00   1.00    2.00    --   98.72 -30.00 -90.00   85
 14  \w     54.00 118.00   1.00    2.00    --   98.72-125.00  60.00   64
 15  \w     76.00 136.00   1.00    2.00    --   98.72  45.00 -90.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1544128000
_diffrn_orient_matrix_UB_12      -0.0102691000
_diffrn_orient_matrix_UB_13      -0.0106551000
_diffrn_orient_matrix_UB_21      -0.0458949000
_diffrn_orient_matrix_UB_22      -0.0723941000
_diffrn_orient_matrix_UB_23      -0.0931375000
_diffrn_orient_matrix_UB_31      -0.0342626000
_diffrn_orient_matrix_UB_32      -0.1252463000
_diffrn_orient_matrix_UB_33      0.0368601000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11582
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.507
_diffrn_reflns_theta_min         4.162
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    8.582
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_description       plate
_exptl_crystal_F_000             812
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.935
_refine_diff_density_min         -0.670
_refine_diff_density_rms         0.126
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         6368
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0676P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1136
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5666
_reflns_number_total             6368
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02246b2.cif
_cod_data_source_block           20200116wangyujie
_cod_original_cell_volume        1717.91(11)
_cod_database_code               1559171
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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:
 C00D(H00D), C00F(H00F), C00R(H00R), C00S(H00S), C00T(H00T)
2.b Secondary CH2 refined with riding coordinates:
 C00G(H00A,H00B), C00N(H00C,H00G), C00O(H00I,H00N), C013(H01D,H01E), C018(H01F,
 H01G)
2.c Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00H(H00H), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M),
 C00P(H00P), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y),
 C00Z(H00Z), C010(H010), C011(H011), C012(H012), C014(H014), C015(H015),
 C016(H016)
2.d Idealised Me refined as rotating group:
 C017(H01A,H01B,H01C)
;
_shelx_res_checksum              8320
_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 1.461
_oxdiff_exptl_absorpt_empirical_full_min 0.754