C(acyl)–C(sp2) and C(sp2)–C(sp2) Suzuki–Miyaura cross-coupling reactions using nitrile-functionalized NHC palladium complexes
Çakır, Sinem; Kavukcu, Serdar Batıkan; Karabıyık, Hande; Rethinam, Senthil; Türkmen, Hayati; RSC Advances 11 (2021) 37684–37699; doi:10.1039/D1RA07231E

data_7243965
_publ_section_title
;
 C(acyl)--C(sp2) and C(sp2)--C(sp2) Suzuki--Miyaura cross-coupling
 reactions using nitrile-functionalized NHC palladium complexes
;
_journal_issue                   60
_journal_name_full               'RSC Advances'
_journal_page_first              37684
_journal_page_last               37699
_journal_paper_doi               10.1039/D1RA07231E
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C16 H17 Br2 N3 Pd'
_chemical_formula_sum            'C16 H17 Br2 N3 Pd'
_chemical_formula_weight         517.54
_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             2021-03-10
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2021-03-19 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;
_cell_angle_alpha                72.709(5)
_cell_angle_beta                 72.523(5)
_cell_angle_gamma                72.840(5)
_cell_formula_units_Z            4
_cell_length_a                   10.0563(5)
_cell_length_b                   14.1910(9)
_cell_length_c                   14.2442(9)
_cell_measurement_reflns_used    2930
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0210
_cell_measurement_theta_min      3.1440
_cell_volume                     1803.4(2)
_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)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0667
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.988
_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     -5.00  24.00   1.00    2.17    --   14.20  77.00  90.00   29
  2  \w    -38.00  37.00   1.00    2.17    --  -16.23  77.00-120.00   75
  3  \w    -75.00   1.00   1.00    2.17    --  -16.23 -37.00  60.00   76
  4  \w      2.00  39.00   1.00    2.00    --   14.20  77.00 -30.00   37
  5  \w    -11.00  35.00   1.00    2.00    --   14.20  77.00-150.00   46
  6  \w    -30.00  48.00   1.00    2.00    --  -16.08  37.00  30.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0108849000
_diffrn_orient_matrix_UB_12      0.0498581000
_diffrn_orient_matrix_UB_13      -0.0126605000
_diffrn_orient_matrix_UB_21      0.0239822000
_diffrn_orient_matrix_UB_22      -0.0106628000
_diffrn_orient_matrix_UB_23      0.0448694000
_diffrn_orient_matrix_UB_31      0.0711943000
_diffrn_orient_matrix_UB_32      -0.0169774000
_diffrn_orient_matrix_UB_33      -0.0265056000
_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  0.0422
_diffrn_reflns_av_unetI/netI     0.0868
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12984
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_min         2.948
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    5.459
_exptl_absorpt_correction_T_max  0.731
_exptl_absorpt_correction_T_min  0.537
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light orange'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.906
_exptl_crystal_description       prism
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.336
_exptl_crystal_size_mid          0.276
_exptl_crystal_size_min          0.161
_refine_diff_density_max         0.917
_refine_diff_density_min         -0.881
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     409
_refine_ls_number_reflns         6760
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1052
_refine_ls_R_factor_gt           0.0488
_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^)+(0.0136P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0792
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4008
_reflns_number_total             6760
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra07231e2.cif
_cod_data_source_block           hande2
_cod_database_code               7243965
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C16 H17 Br2 N3 Pd'
_reflns_odcompleteness_completeness 98.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_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. Uiso/Uaniso restraints and constraints
C16 \\sim C11 \\sim C12 \\sim C15: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 1.7A
C32 \\sim C31 \\sim C30 \\sim C29 \\sim C28: within 1.7A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 1.7A
Ueq(Br4A), Ueq(Br4B): fixed at 0.05 with sigma of 0.1
Ueq(C32), Ueq(C31), Ueq(C30), Ueq(C29), Ueq(C28): fixed at 0.05 with sigma of
0.1
3. Others
 Sof(Br4A)=1-FVAR(1)
 Sof(Br4B)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C26(H26A,H26B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23),
  C24(H24), C25(H25), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32)
4.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              55597
_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 1.086
_oxdiff_exptl_absorpt_empirical_full_min 0.837