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_7243963
_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         'C24 H19 Br2 N5 Pd'
_chemical_formula_sum            'C24 H19 Br2 N5 Pd'
_chemical_formula_weight         643.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 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                90
_cell_angle_beta                 94.651(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.6682(12)
_cell_length_b                   15.9603(13)
_cell_length_c                   8.1346(5)
_cell_measurement_reflns_used    995
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.5680
_cell_measurement_theta_min      3.5170
_cell_volume                     2415.7(3)
_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 0.993
_diffrn_measured_fraction_theta_max 0.992
_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     40.00  81.00   1.00    3.84    --   14.20 178.00   0.00   41
  2  \w    -87.00 -36.00   1.00    3.84    --  -16.08 178.00 -60.00   51
  3  \w    -22.00  34.00   1.00    3.84    --  -16.08  57.00-180.00   56
  4  \w    -31.00   9.00   1.00    3.84    --  -16.08 -77.00 -90.00   40
;
_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      0.0197539000
_diffrn_orient_matrix_UB_12      -0.0117000000
_diffrn_orient_matrix_UB_13      -0.0672785000
_diffrn_orient_matrix_UB_21      0.0238786000
_diffrn_orient_matrix_UB_22      -0.0236219000
_diffrn_orient_matrix_UB_23      0.0541981000
_diffrn_orient_matrix_UB_31      -0.0221997000
_diffrn_orient_matrix_UB_32      -0.0357791000
_diffrn_orient_matrix_UB_33      -0.0137672000
_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  0.0298
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4605
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_min         3.096
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.097
_exptl_absorpt_correction_T_max  0.634
_exptl_absorpt_correction_T_min  0.541
_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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.770
_exptl_crystal_description       prism
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.141
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2274
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0416
_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^)+(0.0167P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0579
_refine_ls_wR_factor_ref         0.0705
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1368
_reflns_number_total             2274
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra07231e2.cif
_cod_data_source_block           hande1
_cod_database_code               7243963
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C24 H19 Br2 N5 Pd'
_reflns_odcompleteness_completeness 99.16
_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
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13)
;
_shelx_res_checksum              39469
_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 1.199
_oxdiff_exptl_absorpt_empirical_full_min 0.802