Orthometallated Pd(ii) C^N^S pincer complex catalyzed sustainable synthesis of bis(indolyl)methanes via acceptorless dehydrogenative coupling of alcohols
Clinton, Savarimuthu Selvan; Ramesh, Rengan; Malecki, Jan Grzegorz; Catalysis Science & Technology 13 (2023) 3358–3365; doi:10.1039/D3CY00333G

data_1568859
_publ_section_title
;
 Orthometallated Pd(ii) C^N^S pincer complex catalyzed sustainable
 synthesis of bis(indolyl)methanes via acceptorless dehydrogenative
 coupling of alcohols
;
_journal_issue                   11
_journal_name_full               'Catalysis Science &amp; Technology'
_journal_page_first              3358
_journal_page_last               3365
_journal_paper_doi               10.1039/D3CY00333G
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C32 H26 N3 O P Pd S'
_chemical_formula_sum            'C32 H26 N3 O P Pd S'
_chemical_formula_weight         637.99
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2021-02-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_audit_update_record
;
2021-02-27 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                71.591(4)
_cell_angle_beta                 74.372(4)
_cell_angle_gamma                75.139(4)
_cell_formula_units_Z            2
_cell_length_a                   9.8480(4)
_cell_length_b                   11.6412(5)
_cell_length_c                   14.0807(6)
_cell_measurement_reflns_used    5253
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.0280
_cell_measurement_theta_min      3.6820
_cell_volume                     1448.83(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (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)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4015
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.866
_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    -31.00  20.00   1.00   26.81    --    9.90 100.00 102.00   51
  2  \w      1.00  51.00   1.00   26.81    --    9.90-100.00  -2.00   50
  3  \w    -36.00  63.00   1.00   26.81    --  -11.62  38.00  60.00   99
  4  \w    -40.00  -3.00   1.00   26.81    --  -11.62  77.00  90.00   37
  5  \w    -31.00  63.00   1.00   26.81    --  -11.62  38.00 -90.00   94
  6  \w    -92.00  12.00   1.00   26.81    --  -11.62 -19.00  90.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0433461000
_diffrn_orient_matrix_UB_12      0.0361859000
_diffrn_orient_matrix_UB_13      0.0332206000
_diffrn_orient_matrix_UB_21      0.0366550000
_diffrn_orient_matrix_UB_22      -0.0374286000
_diffrn_orient_matrix_UB_23      0.0394431000
_diffrn_orient_matrix_UB_31      0.0507442000
_diffrn_orient_matrix_UB_32      0.0395450000
_diffrn_orient_matrix_UB_33      -0.0168359000
_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  0.0349
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.866
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17484
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.495
_diffrn_reflns_theta_min         3.420
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.798
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.133
_refine_diff_density_min         -0.648
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         6991
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0387
_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^)+(0.0339P)^2^+0.4229P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0887
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5178
_reflns_number_total             6991
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cy00333g2.cif
_cod_data_source_block           cs3
_cod_depositor_comments          'Adding full bibliography for 1568859.cif.'
_cod_original_cell_volume        1448.84(12)
_cod_database_code               1568859
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C32 H27 Cl1 N3 O1 P1 Pd1'
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23),
  C24(H24), C25(H25), C26(H26), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32)
;
_shelx_res_checksum              56615
_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 1.236
_oxdiff_exptl_absorpt_empirical_full_min 0.825