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_7123277
_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         '2(C27 H36 I N2 Pd)'
_chemical_formula_sum            'C54 H72 I2 N4 Pd2'
_chemical_formula_weight         1243.75
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 107.883(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.6817(12)
_cell_length_b                   10.4999(7)
_cell_length_c                   20.3690(12)
_cell_measurement_reflns_used    4306
_cell_measurement_temperature    99.9(2)
_cell_measurement_theta_max      73.6230
_cell_measurement_theta_min      4.3690
_cell_volume                     5430.8(6)
_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      99.9(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4409
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9750
_diffrn_measured_fraction_theta_max 0.9749
_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 -6.00 21.00 1.00 61.95 -- -42.40 38.00 -60.00 27 2 \w -116.00 -11.00 1.00 61.95 -- -42.40 -73.00 157.00 105 3 \w -64.00 -15.00 1.00 61.95 -- -42.40 38.00 -60.00 49 4 \w 2.00 89.00 1.00 61.95 -- 42.40-125.00 60.00 87 5 \w 39.00 89.00 1.00 247.79 -- 109.91 -61.00 60.00 50 6 \w 70.00 114.00 1.00 247.79 -- 109.91-109.00 75.00 44 7 \w 76.00 158.00 1.00 247.79 -- 109.91 125.00-180.00 82 8 \w 71.00 104.00 1.00 247.79 -- 109.91 -45.00 60.00 33
;
_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      0.0368608000
_diffrn_orient_matrix_UB_12      0.0768754000
_diffrn_orient_matrix_UB_13      0.0598668000
_diffrn_orient_matrix_UB_21      0.0326651000
_diffrn_orient_matrix_UB_22      -0.1209981000
_diffrn_orient_matrix_UB_23      0.0266575000
_diffrn_orient_matrix_UB_31      0.0354890000
_diffrn_orient_matrix_UB_32      0.0310397000
_diffrn_orient_matrix_UB_33      -0.0449428000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_Laue_measured_fraction_full 0.750
_diffrn_reflns_Laue_measured_fraction_max 0.749
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13006
_diffrn_reflns_point_group_measured_fraction_full 0.750
_diffrn_reflns_point_group_measured_fraction_max 0.749
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.000
_diffrn_reflns_theta_min         3.481
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    14.539
_exptl_absorpt_correction_T_max  0.766
_exptl_absorpt_correction_T_min  0.576
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
'CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Numerical absorption correction based on gaussian integration over 			a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_description       prism
_exptl_crystal_F_000             2488
_exptl_crystal_size_max          0.069
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.032
_refine_diff_density_max         2.448
_refine_diff_density_min         -1.948
_refine_diff_density_rms         0.149
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     568
_refine_ls_number_reflns         7419
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0617
_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^)+(0.0756P)^2^+47.7539P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1483
_refine_ls_wR_factor_ref         0.1679
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5627
_reflns_number_total             7419
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc02239b2.cif
_cod_data_source_block           dea-528
_cod_database_code               7123277
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C54 N  H64 Pd2 I2'
_reflns_odcompleteness_completeness 75.69
_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. Restrained distances
 C51-C53A \\sim C51-C53B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C57) = Uanis(C39)
Uanis(C52) = Uanis(C53A) = Uanis(C53B)
4. Others
 Sof(C53B)=Sof(H53D)=Sof(H53E)=Sof(H53F)=Sof(H51A)=1-FVAR(1)
 Sof(C53A)=Sof(H53A)=Sof(H53B)=Sof(H53C)=Sof(H51)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C31(H31), C57(H57), C25(H25), C60(H60), C22(H22), C28(H28), C54(H54),
 C51(H51), C51(H51A)
5.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C20(H20), C7(H7), C12(H12), C36(H36), C9(H9), C42(H42), C41(H41),
 C48(H48), C37(H37), C38(H38), C18(H18), C8(H8), C19(H19), C49(H49), C47(H47)
5.c Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C27(H27A,H27B,H27C), C59(H59A,H59B,H59C), C62(H62A,H62B,
 H62C), C32(H32A,H32B,H32C), C24(H24A,H24B,H24C), C56(H56A,H56B,H56C), C58(H58A,
 H58B,H58C), C26(H26A,H26B,H26C), C55(H55A,H55B,H55C), C53A(H53A,H53B,H53C),
 C53B(H53D,H53E,H53F), C23(H23A,H23B,H23C), C61(H61A,H61B,H61C), C30(H30A,H30B,
 H30C), C29(H29A,H29B,H29C), C52(H52A,H52B,H52C)
;
_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 1.823
_oxdiff_exptl_absorpt_empirical_full_min 0.697