Amino acid-derived bisphenolate palladium complexes as C-C coupling catalysts
Fazekas, Eszter; Jenkins, David T.; Forbes, Andrew A.; Gallagher, Brendan; Rosair, Georgina; McIntosh, Ruaraidh D.; Dalton Transactions  (2021) –; doi:10.1039/D1DT03068J

data_7708836
_publ_section_title
;
 Amino acid-derived bisphenolate palladium complexes as C-C coupling
 catalysts
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_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D1DT03068J
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C40 H66 N2 O4 Pd'
_chemical_formula_sum            'C40 H66 N2 O4 Pd'
_chemical_formula_weight         745.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-02-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-02-18 deposited with the CCDC.	2021-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.0420(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9356(4)
_cell_length_b                   26.4605(11)
_cell_length_c                   15.5658(6)
_cell_measurement_reflns_used    9337
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      26.357
_cell_measurement_theta_min      3.078
_cell_volume                     3952.0(3)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PhotonIII detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            146440
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.401
_diffrn_reflns_theta_min         2.677
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.509
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0582 before and 0.0538 after correction.
The Ratio of minimum to maximum transmission is 0.9143.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       block
_exptl_crystal_F_000             1592
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 6940 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.084(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     905
_refine_ls_number_reflns         15877
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0293
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0226P)^2^+3.7935P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0646
_refine_ls_wR_factor_ref         0.0656
_reflns_Friedel_coverage         0.959
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                15237
_reflns_number_total             15877
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1dt03068j2.cif
_cod_data_source_block           ef89
_cod_database_code               7708836
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.905
_shelx_estimated_absorpt_t_min   0.862
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C13A-C12 = C15-C12 = C15A-C12 = C14-C12 = C14A-C12
 1.52 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C14A) = Uanis(C15)
4. Others
 Sof(HU)=Sof(HV)=Sof(C20A)=Sof(H8DA)=Sof(H9DA)=Sof(H0EA)=1-FVAR(1)
 Sof(HW)=Sof(HX)=Sof(C20)=Sof(HY)=Sof(HZ)=Sof(H0AA)=FVAR(1)
 Sof(C15A)=Sof(H1EA)=Sof(H2EA)=Sof(H3EA)=Sof(C14A)=Sof(H7EA)=Sof(H8EA)=
 Sof(H9EA)=1-FVAR(2)
 Sof(C14)=Sof(HM)=Sof(HN)=Sof(HO)=Sof(C15)=Sof(HP)=Sof(HQ)=Sof(HR)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C1(H,HA), C16(HS,HT), C19(HU,HV), C19(HW,HX), C21(H1AA,H2AA), C36(H3CA,H4CA),
 C38(H8CA,H9CA), C40(H3DA,H4DA), C1'(H1'A,H1'B), C16'(H16A,H16B), C19'(H19A,
 H19B), C21'(H21A,H21B), C36'(H36A,H36B), C38'(H38A,H38B), C40'(H40A,H40B)
5.b Aromatic/amide H refined with riding coordinates:
 C5(HB), C7(HC), C25(H3AA), C27(H4AA), C5'(H5'), C7'(H7'), C25'(H25'),
 C27'(H27')
5.c Idealised Me refined as rotating group:
 C9(HD,HE,HF), C10(HG,HH,HI), C11(HJ,HK,HL), C14(HM,HN,HO), C15(HP,HQ,HR),
 C20(HY,HZ,H0AA), C29(H5AA,H6AA,H7AA), C30(H8AA,H9AA,H0BA), C31(H1BA,H2BA,H3BA),
  C33(H4BA,H5BA,H6BA), C34(H7BA,H8BA,H9BA), C35(H0CA,H1CA,H2CA), C37(H5CA,H6CA,
 H7CA), C39(H0DA,H1DA,H2DA), C41(H5DA,H6DA,H7DA), C9'(H9'A,H9'B,H9'C),
 C10'(H10A,H10B,H10C), C11'(H11A,H11B,H11C), C13'(H13A,H13B,H13C), C14'(H14A,
 H14B,H14C), C15'(H15A,H15B,H15C), C20'(H20A,H20B,H20C), C29'(H29A,H29B,H29C),
 C30'(H30A,H30B,H30C), C31'(H31A,H31B,H31C), C33'(H33A,H33B,H33C), C34'(H34A,
 H34B,H34C), C35'(H35A,H35B,H35C), C37'(H37A,H37B,H37C), C39'(H39A,H39B,H39C),
 C41'(H41A,H41B,H41C), C20A(H8DA,H9DA,H0EA), C15A(H1EA,H2EA,H3EA), C13A(H4EA,
 H5EA,H6EA), C14A(H7EA,H8EA,H9EA)
;
_shelx_res_checksum              61940
_olex2_submission_special_instructions 'No special instructions were received'