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_7243964
_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         'C17 H16 Br2 N4 Pd'
_chemical_formula_sum            'C17 H16 Br2 N4 Pd'
_chemical_formula_weight         542.56
_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             2021-03-12
_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                90.731(10)
_cell_angle_beta                 100.478(10)
_cell_angle_gamma                106.482(10)
_cell_formula_units_Z            2
_cell_length_a                   7.4786(9)
_cell_length_b                   11.0996(11)
_cell_length_c                   11.7959(16)
_cell_measurement_reflns_used    1351
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.9700
_cell_measurement_theta_min      7.1420
_cell_volume                     921.1(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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0667
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.987
_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     10.00  79.00   1.00    2.30    --   14.20  37.00  60.00   69
  2  \w    -20.00  13.00   1.00    2.30    --   14.20 -99.00-120.00   33
  3  \w    -27.00  39.00   1.00    2.30    --   14.20 -77.00 -60.00   66
  4  \w    -34.00   8.00   1.00    2.30    --  -16.23 -77.00-150.00   42
  5  \w    -39.00 -14.00   1.00    2.30    --  -16.23 -77.00-180.00   25
  6  \w    -36.00  33.00   1.00    2.30    --  -16.23  77.00  90.00   69
  7  \w    -17.00   8.00   1.00    2.30    --  -16.23 -77.00   0.00   25
  8  \w    -29.00  41.00   1.00    2.30    --  -16.23  57.00 150.00   70
;
_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      0.0493483000
_diffrn_orient_matrix_UB_12      0.0036873000
_diffrn_orient_matrix_UB_13      0.0578806000
_diffrn_orient_matrix_UB_21      0.0208928000
_diffrn_orient_matrix_UB_22      0.0665419000
_diffrn_orient_matrix_UB_23      0.0023555000
_diffrn_orient_matrix_UB_31      -0.0853900000
_diffrn_orient_matrix_UB_32      -0.0045303000
_diffrn_orient_matrix_UB_33      0.0200289000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0788
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3823
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.653
_diffrn_reflns_theta_min         2.895
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    5.351
_exptl_absorpt_correction_T_max  0.574
_exptl_absorpt_correction_T_min  0.305
_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    1.956
_exptl_crystal_description       prism
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.286
_exptl_crystal_size_min          0.131
_refine_diff_density_max         1.474
_refine_diff_density_min         -1.799
_refine_diff_density_rms         0.370
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3823
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.1117
_refine_ls_R_factor_gt           0.0637
_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^)+(0.1383P)^2^+4.4641P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2259
_refine_ls_wR_factor_ref         0.2555
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2204
_reflns_number_total             3823
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 1.2622\% 
 around [-0.17 0.93 -0.32] (reciprocal) or [-0.06 0.96 -0.29] (direct)
;
_cod_data_source_file            d1ra07231e2.cif
_cod_data_source_block           hande3
_cod_database_code               7243964
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C17 H16 Br2 N4 Pd'
_shelx_estimated_absorpt_t_max   0.541
_shelx_estimated_absorpt_t_min   0.229
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.950(3)
 0.050(3)
2. 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
3. Rigid body (RIGU) restrains
 C1, N3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
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)
4.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_shelx_res_checksum              44096
_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 1.590
_oxdiff_exptl_absorpt_empirical_full_min 0.717
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2