Mono-N-Protected Amino Acid Ligands Stabilize Dimeric Palladium(II) Complexes of Importance to C-H Functionalization
Gair, Joe J.; Haines, Brandon E.; Filatov, Alexander S.; Musaev, D. G.; Lewis, Jared C.; Chem. Sci.  (2017) –; doi:10.1039/C7SC01674C

data_1546339
_publ_section_title
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 Mono-N-Protected Amino Acid Ligands Stabilize Dimeric Palladium(II)
 Complexes of Importance to C-H Functionalization
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC01674C
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H38 F6 N4 O6 Pd2, C2 H3 N'
_chemical_formula_sum            'C32 H41 F6 N5 O6 Pd2'
_chemical_formula_weight         918.50
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-12-28
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2017-04-15 deposited with the CCDC.
2017-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3180(4)
_cell_length_b                   9.8627(4)
_cell_length_c                   40.0507(19)
_cell_measurement_reflns_used    9911
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.26
_cell_measurement_theta_min      2.41
_cell_volume                     3680.7(3)
_computing_cell_refinement       'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX3 v.2015.9-0 (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V.8.35A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics
;
OLEX2: a complete structure solution, refinement and analysis program 
Dolomanov et al., 2009

Mercury: visualization and analysis of crystal structures
Macrae, et al., 2006

O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann.
J. Appl. Cryst. (2009). 42, 339-341;

C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst. (2006). 39, 453-457.
;
_computing_publication_material
;
 APEX3 v.2015.5-2 (Bruker AXS Inc., 2015)
 OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement  'XL-2014/7 (Sheldrick, 2015b)'
_computing_structure_solution    'XT 2014/5 (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0715
_diffrn_reflns_av_unetI/netI     0.0850
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            39996
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.364
_diffrn_reflns_theta_min         2.127
_diffrn_source                   'INCOATEC ImuS micro-focus source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.056
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. 
wR2(int) was 0.0725 before and 0.0638 after correction. 
The Ratio of minimum to maximum transmission is 0.9320. 
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_description       plate
_exptl_crystal_F_000             1848
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.747
_refine_diff_density_rms         0.125
_refine_ls_abs_structure_details
;
 Flack x determined using 1989 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         6909
_refine_ls_number_restraints     45
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0435
_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^)+(0.0157P)^2^+4.0298P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0576
_refine_ls_wR_factor_ref         0.0620
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_full    0.951
_reflns_Friedel_fraction_max     0.871
_reflns_number_gt                5570
_reflns_number_total             6909
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc01674c6.cif
_cod_data_source_block           complex_6b
_cod_database_code               1546339
_shelx_estimated_absorpt_t_max   0.866
_shelx_estimated_absorpt_t_min   0.715
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 O5, O4, C26, C27
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
 F3, F1, F2, C8
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C32, C31, N5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Ternary CH refined with riding coordinates:
 C12(H12), C27(H27)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C22(H22A,H22B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4A), C17(H17), C18(H18), C19(H19)
3.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C15(H15A,H15B,
 H15C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C28(H28A,H28B,H28C), C30(H30A,
 H30B,H30C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              99246
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'