Direct C‒H heteroarylation by an acenaphthyl-based α-diimine palladium complex: improvement of the reaction efficiency for bi(hetero)aryls under aerobic conditions
Chen, Fu-Min; Huang, Fei-Dong; Yao, Xue-Yi; Li, Tian; Liu, Feng-Shou; Organic Chemistry Frontiers 4 (2017) 2336–; doi:10.1039/C7QO00562H

data_1553842
_publ_section_title
;
 Direct C--H heteroarylation by an acenaphthyl-based \a-diimine palladium
 complex: improvement of the reaction efficiency for bi(hetero)aryls under
 aerobic conditions
;
_journal_issue                   12
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2336
_journal_paper_doi               10.1039/C7QO00562H
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C40 H48 Cl2 N2 Pd, 2(O)'
_chemical_formula_sum            'C40 H48 Cl2 N2 O2 Pd'
_chemical_formula_weight         766.10
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-05-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-06-28 deposited with the CCDC.
2017-08-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.489(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7394(11)
_cell_length_b                   19.8380(19)
_cell_length_c                   16.5546(12)
_cell_measurement_reflns_used    5100
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.4770
_cell_measurement_theta_min      3.7450
_cell_volume                     3843.5(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  32.00   1.00    8.24    --   11.90  37.00   0.00   27
  2  \w    -32.00  58.00   1.00    8.24    --  -11.66  37.00  60.00   90
  3  \w     38.00  72.00   1.00    8.24    --   11.90 178.00-180.00   34
  4  \w    -81.00  13.00   1.00    8.24    --  -11.66 -37.00-120.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0235430000
_diffrn_orient_matrix_UB_12      -0.0147050000
_diffrn_orient_matrix_UB_13      -0.0340594000
_diffrn_orient_matrix_UB_21      -0.0220105000
_diffrn_orient_matrix_UB_22      0.0269683000
_diffrn_orient_matrix_UB_23      -0.0245994000
_diffrn_orient_matrix_UB_31      0.0514065000
_diffrn_orient_matrix_UB_32      0.0182454000
_diffrn_orient_matrix_UB_33      0.0089556000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_av_unetI/netI     0.0906
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19000
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.482
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86150
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       block
_exptl_crystal_F_000             1592
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.497
_refine_diff_density_min         -1.657
_refine_diff_density_rms         0.142
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         6750
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.185
_refine_ls_R_factor_all          0.1182
_refine_ls_R_factor_gt           0.0986
_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^)+55.6780P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2046
_refine_ls_wR_factor_ref         0.2146
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5321
_reflns_number_total             6750
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00562h2.cif
_cod_data_source_block           exp_597
_cod_database_code               1553842
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.925
_shelx_estimated_absorpt_t_min   0.891
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00D(H00D), C00E(H00E), C00F(H00F), C00L(H00L),
 C00N(H00N), C00O(H00O), C00Q(H00Q), C00T(H00T), C00U(H00U), C00V(H00V)
2.b Idealised Me refined as rotating group:
 C00Y(H00A,H00C,H00G), C010(H01A,H01B,H01C), C011(H01D,H01E,H01F), C012(H01G,
 H01H,H01I), C013(H01J,H01K,H01L), C014(H01M,H01N,H01O), C015(H01P,H01Q,H01R),
 C016(H01S,H01T,H01U), C018(H01V,H01W,H01X), C019(H01Y,H,HA), C01A(H01Z,HB,HC),
 C01B(H01,HD,HE)
;
_olex2_date_sample_data_collection 2017-05-27
_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 1.260
_oxdiff_exptl_absorpt_empirical_full_min 0.768