Effect of 2-Substituents on Allyl-Supported Precatalysts for the Suzuki‒Miyaura Reaction: Relating Catalytic Efficiency to the Stability of Palladium(I) Bridging Allyl Dimers
Hruszkewycz, Damian P.; Guard, Louise M.; Balcells, David; Feldman, Nicola; Hazari, Nilay; Tilset, Mats; Organometallics 34 (2015) 381–; doi:10.1021/om501250y

data_4085322
_publ_section_title
;
 Effect of 2-Substituents on Allyl-Supported Precatalysts for the
 Suzuki--Miyaura Reaction: Relating Catalytic Efficiency to the Stability
 of Palladium(I) Bridging Allyl Dimers
;
_journal_issue                   1
_journal_name_full               Organometallics
_journal_page_first              381
_journal_paper_doi               10.1021/om501250y
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         'C29 H38 Cl0.5 N2.5 Pd'
_chemical_formula_sum            'C29 H38 Cl0.5 N2.5 Pd'
_chemical_formula_weight         545.74
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_audit_creation_date             2014-08-14
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
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_cell_length_b                   11.8025(2)
_cell_length_c                   24.259(3)
_cell_measurement_reflns_used    74642
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     5369.2(8)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
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CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_diffrn_detector                 RX
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
scan:
    Number of images: 90
               Slice: 20.0000 - 200.0000
         Image width: 2.0000
            Exp time: 60.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 0.0000
                 Phi: 0.0000
                 XTD: 127.4000
              2theta: -0.0322
scan:
    Number of images: 90
               Slice: 20.0000 - 200.0000
         Image width: 2.0000
            Exp time: 60.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 120.0000
                 XTD: 127.4000
              2theta: -0.0322
scan:
    Number of images: 90
               Slice: 20.0000 - 200.0000
         Image width: 2.0000
            Exp time: 60.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 0.0000
                 Phi: 180.0000
                 XTD: 127.4000
              2theta: -0.0322
scan:
    Number of images: 90
               Slice: 20.0000 - 200.0000
         Image width: 2.0000
            Exp time: 60.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 0.0000
                 XTD: 127.4000
              2theta: -0.0322
scan:
    Number of images: 90
               Slice: 20.0000 - 200.0000
         Image width: 2.0000
            Exp time: 60.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 240.0000
                 XTD: 127.4000
              2theta: -0.0322
scan:
    Number of images: 90
               Slice: 20.0000 - 200.0000
         Image width: 2.0000
            Exp time: 60.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 90.0000
                 XTD: 127.4000
              2theta: -0.0322
scan:
    Number of images: 90
               Slice: 20.0000 - 200.0000
         Image width: 2.0000
            Exp time: 60.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 54.0000
                 Phi: 180.0000
                 XTD: 127.4000
              2theta: -0.0322
;
_diffrn_measurement_device
;
Crystal Goniometer
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_diffrn_measurement_device_type  Spyder
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_diffrn_orient_matrix_UB_11      0.010830
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_diffrn_orient_matrix_UB_13      0.043292
_diffrn_orient_matrix_UB_21      -0.041986
_diffrn_orient_matrix_UB_22      -0.010144
_diffrn_orient_matrix_UB_23      -0.014277
_diffrn_orient_matrix_UB_31      -0.002558
_diffrn_orient_matrix_UB_32      -0.064101
_diffrn_orient_matrix_UB_33      -0.034528
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1439
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            128336
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         3.114
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.761
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       plate
_exptl_crystal_F_000             2272
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.112
_refine_diff_density_min         -1.189
_refine_diff_density_rms         0.177
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.290
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     594
_refine_ls_number_reflns         6159
_refine_ls_number_restraints     569
_refine_ls_restrained_S_all      1.236
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0970
_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^)+208.1514P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2202
_refine_ls_wR_factor_ref         0.2239
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5646
_reflns_number_total             6159
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om501250y_si_002.cif
_cod_data_source_block           '_II-CN'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        5369.2(7)
_cod_original_formula_sum        'C29 H38 Cl0.50 N2.50 Pd'
_cod_database_code               4085322
_shelxl_version_number           2013-4
_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
 C25-C20 \\sim C24-C25 \\sim C23-C24 \\sim C22-C23 \\sim C22-C21 \\sim C20-C21
 with sigma of 0.02
 C20-C23 \\sim C25-C22 \\sim C24-C21
 with sigma of 0.02
 C28-C26 \\sim C27-C26 \\sim C31-C29 \\sim C30-C29
 with sigma of 0.02
 C31-C30 \\sim C28-C27
 with sigma of 0.02
 C27A-C26A \\sim C28A-C26A \\sim C29A-C31A \\sim C30A-C29A
 with sigma of 0.02
 C31A-C30A \\sim C28A-C27A
 with sigma of 0.02
 C11-C6 \\sim C7-C6 \\sim C8-C7 \\sim C9-C8 \\sim C10-C9 \\sim C11-C10
 with sigma of 0.02
 C11-C8 \\sim C10-C7 \\sim C9-C6
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 Pd1, C5, C1, C2, Cl1, N3A, N2, N3, N2A, H1A, H1B, C3, C4, C19A, C20A, C6, C18,
  C20, C19, C6A, C18A, H3A, H3B, N1, H19A, C21A, C7, C11, H18, C25, C21, H19,
 C7A, C11A, H18A, C26A, C24A, C22A, C29A, C8, C15, C12, C10, C24, C26, C22, C29,
  C15A, C8A, C10A, C12A, H26A, C28A, C27A, H24A, C23A, H22A, C30A, H29A, C31A,
 H8, C9, H15, C16, C17, H12, C14, C13, H10, H24, C23, C28, C27, H26, H22, C31,
 C30, H29, H15A, C17A, C16A, H8A, C9A, H10A, C13A, H12A, C14A, H28D, H28E, H28F,
  H27D, H27E, H27F, H23A, H30D, H30E, H30F, H31D, H31E, H31F, H9, H16A, H16B,
 H16C, H17A, H17B, H17C, H14A, H14B, H14C, H13A, H13B, H13C, H23, H28A, H28B,
 H28C, H27A, H27B, H27C, H31A, H31B, H31C, H30A, H30B, H30C, H17D, H17E, H17F,
 H16D, H16E, H16F, H9A, H13D, H13E, H13F, H14D, H14E, H14F, C25A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(N3A)=Sof(C19A)=Sof(H19A)=Sof(C26A)=Sof(H26A)=Sof(C25A)=Sof(C24A)=
 Sof(H24A)=Sof(C23A)=Sof(H23A)=Sof(C22A)=Sof(H22A)=Sof(C21A)=Sof(C20A)=Sof(C6A)=
 Sof(C7A)=Sof(C15A)=Sof(H15A)=Sof(C17A)=Sof(H17D)=Sof(H17E)=Sof(H17F)=Sof(C16A)=
 Sof(H16D)=Sof(H16E)=Sof(H16F)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=
 Sof(H10A)=Sof(C11A)=Sof(C13A)=Sof(H13D)=Sof(H13E)=Sof(H13F)=Sof(C12A)=
 Sof(H12A)=Sof(C14A)=Sof(H14D)=Sof(H14E)=Sof(H14F)=Sof(C28A)=Sof(H28D)=
 Sof(H28E)=Sof(H28F)=Sof(C30A)=Sof(H30D)=Sof(H30E)=Sof(H30F)=Sof(C29A)=
 Sof(H29A)=Sof(C31A)=Sof(H31D)=Sof(H31E)=Sof(H31F)=Sof(C27A)=Sof(H27D)=
 Sof(H27E)=Sof(H27F)=Sof(N2A)=Sof(C18A)=Sof(H18A)=1-FVAR(1)
 Sof(C6)=Sof(N2)=Sof(C7)=Sof(C8)=Sof(H8)=Sof(C12)=Sof(H12)=Sof(C11)=Sof(C10)=
 Sof(H10)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=Sof(C18)=Sof(H18)=Sof(C9)=
 Sof(H9)=Sof(C15)=Sof(H15)=Sof(C25)=Sof(C20)=Sof(C24)=Sof(H24)=Sof(C16)=
 Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(C21)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=
 Sof(C23)=Sof(H23)=Sof(C22)=Sof(H22)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H17C)=
 Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(H31C)=Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(H28C)=
 Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(H30C)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=
 Sof(C29)=Sof(H29)=Sof(C26)=Sof(H26)=Sof(C19)=Sof(H19)=Sof(N3)=FVAR(1)
 Fixed Sof: C1(0.5) H1A(0.5) H1B(0.5) N1(0.5) C3(0.5) H3A(0.5) H3B(0.5)
 C2(0.5) C4(0.5) Cl1(0.5)
5.a Ternary CH refined with riding coordinates:
 C12(H12), C15(H15), C26A(H26A), C15A(H15A), C12A(H12A), C29(H29), C26(H26),
 C29A(H29A)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B)
5.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C18(H18), C9(H9), C19A(H19A), C24(H24), C23(H23), C22(H22),
 C24A(H24A), C23A(H23A), C22A(H22A), C8A(H8A), C9A(H9A), C10A(H10A), C19(H19),
 C18A(H18A)
5.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C13(H13A,H13B,H13C), C17(H17A,H17B,
 H17C), C17A(H17D,H17E,H17F), C16A(H16D,H16E,H16F), C13A(H13D,H13E,H13F),
 C14A(H14D,H14E,H14F), C31(H31A,H31B,H31C), C28(H28A,H28B,H28C), C30(H30A,H30B,
 H30C), C27(H27A,H27B,H27C), C28A(H28D,H28E,H28F), C30A(H30D,H30E,H30F),
 C31A(H31D,H31E,H31F), C27A(H27D,H27E,H27F)
;
_shelx_res_checksum              96500
_shelx_hkl_checksum              34586
_olex2_submission_special_instructions 'No special instructions were received'