Dihalogen-bridged NHC-palladium(I) dimers: synthesis, characterisation and applications in cross-coupling reactions
Goossen, Lukas J.; Pirkl, Nico; Del Grosso , Alessandro; Mallick, Bert; Doppiu, Angelino; Chemical Communications  (2019) –; doi:10.1039/C9CC02239B

data_7123278
_publ_section_title
;
 Dihalogen-bridged NHC-palladium(I) dimers: synthesis, characterisation
 and applications in cross-coupling reactions
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC02239B
_journal_year                    2019
_chemical_formula_moiety         'C54 H72 Br2 N4 Pd, 2(C4 H8 O2)'
_chemical_formula_sum            'C62 H88 Br2 N4 O4 Pd'
_chemical_formula_weight         1219.58
_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'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-07
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.03.09 svn.r3491 for OlexSys, GUI svn.r5477)
;
_audit_update_record
;
2019-02-07 deposited with the CCDC.    2019-04-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.910(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.6001(5)
_cell_length_b                   13.1062(3)
_cell_length_c                   22.5609(5)
_cell_measurement_reflns_used    8521
_cell_measurement_temperature    108(10)
_cell_measurement_theta_max      76.1170
_cell_measurement_theta_min      4.0020
_cell_volume                     5960.1(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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      108(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4409
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.978
_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 22.00 117.00 1.00 1.00 -- 42.65 38.00 0.00 95
 2 \w 74.00 112.00 1.00 1.00 -- 42.65 136.00-129.00 38
 3 \w 119.00 155.00 1.00 2.18 -- 112.00 45.00-120.00 36
 4 \w 133.00 158.00 1.00 2.18 -- 112.00 77.00 -30.00 25
 5 \w 121.00 158.00 1.00 2.18 -- 112.00 45.00 90.00 37
 6 \w 105.00 147.00 1.00 2.18 -- 112.00 111.00 90.00 42
 7 \w 79.00 126.00 1.00 2.18 -- 112.00 77.00 -30.00 47
 8 \w 104.00 153.00 1.00 2.18 -- 112.00 45.00-180.00 49
 9 \w 40.00 128.00 1.00 2.18 -- 112.00 -77.00 -30.00 88
 10 \w 40.00 114.00 1.00 2.18 -- 112.00-111.00 150.00 74
 11 \w 36.00 115.00 1.00 2.18 -- 112.00-111.00 -30.00 79
 12 \w 41.00 132.00 1.00 2.18 -- 112.00 -45.00 -30.00 91
 13 \w 9.00 97.00 1.00 1.00 -- 42.65-125.00 90.00 88
 14 \w -102.00 -70.00 1.00 1.00 -- -42.65 -38.00 -60.00 32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0302332000
_diffrn_orient_matrix_UB_12      -0.1077637000
_diffrn_orient_matrix_UB_13      -0.0102954000
_diffrn_orient_matrix_UB_21      0.0687667000
_diffrn_orient_matrix_UB_22      -0.0471759000
_diffrn_orient_matrix_UB_23      0.0245230000
_diffrn_orient_matrix_UB_31      -0.0138439000
_diffrn_orient_matrix_UB_32      0.0008929000
_diffrn_orient_matrix_UB_33      0.0645181000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14530
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.249
_diffrn_reflns_theta_min         4.023
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.452
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.276
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       prism
_exptl_crystal_F_000             2544
_exptl_crystal_size_max          0.329
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.116
_refine_diff_density_max         0.973
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         6112
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0288
_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^)+(0.0425P)^2^+9.2983P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0780
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5891
_reflns_number_total             6112
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc02239b2.cif
_cod_data_source_block           dea-469b
_cod_database_code               7123278
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C62 H88 Br2 N4 O4 Pd'
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Ternary CH refined with riding coordinates:
 C12(H12), C14(H14), C28(H28), C30(H30)
2.b Secondary CH2 refined with riding coordinates:
 C82(H82A,H82B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C15(H15), C16(H16), C19(H19), C26(H26), C27(H27), C99(H99)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C23(H23A,H23B,H23C), C29(H29A,H29B,H29C), C32(H32A,H32B,
 H32C), C33(H33A,H33B,H33C), C36(H36A,H36B,H36C), C41(H41A,H41B,H41C), C80(H80A,
 H80B,H80C), C81(H81A,H81B,H81C), C84(H84A,H84B,H84C)
;
_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 1.255
_oxdiff_exptl_absorpt_empirical_full_min 0.831