Direct ortho-C-H functionalization of aromatic alcohols masked by acetone oxime ether via exo-palladacycle.
Guo, Kun; Chen, Xiaolan; Guan, Mingyu; Zhao, Yingsheng; Organic letters 17 (2015) 1802–1805; doi:10.1021/acs.orglett.5b00594

data_1554907
_publ_section_title
;
 Direct ortho-C-H functionalization of aromatic alcohols masked by acetone
 oxime ether via exo-palladacycle.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1802
_journal_page_last               1805
_journal_paper_doi               10.1021/acs.orglett.5b00594
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C28 H36 N2 O10 Pd3'
_chemical_formula_sum            'C28 H36 N2 O10 Pd3'
_chemical_formula_weight         879.79
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-10-06
_audit_creation_method
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Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
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_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.2684(4)
_cell_length_b                   13.1049(5)
_cell_length_c                   14.9823(6)
_cell_measurement_reflns_used    4674
_cell_measurement_temperature    223.00(10)
_cell_measurement_theta_max      29.9510
_cell_measurement_theta_min      3.9810
_cell_volume                     1606.80(12)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      223.00(10)
_diffrn_detector_area_resol_mean 10.4471
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -45.00   26.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       13.8077  -37.0000  120.0000 71

  2 omega  -59.00   12.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       13.8077  -57.0000   60.0000 71

  3 omega   44.00   96.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       13.8077  178.0000  -60.0000 52

  4 omega  -87.00  -53.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5889  178.0000 -120.0000 34

  5 omega   -1.00   27.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.5889  -99.0000 -150.0000 28
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_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0284475000
_diffrn_orient_matrix_UB_12      0.0439155000
_diffrn_orient_matrix_UB_13      0.0251886000
_diffrn_orient_matrix_UB_21      0.0818317000
_diffrn_orient_matrix_UB_22      -0.0165326000
_diffrn_orient_matrix_UB_23      0.0003011000
_diffrn_orient_matrix_UB_31      0.0036750000
_diffrn_orient_matrix_UB_32      0.0270143000
_diffrn_orient_matrix_UB_33      -0.0406152000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
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_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9785
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.994
_diffrn_reflns_theta_min         2.935
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.716
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
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Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.818
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.922
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3504
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0288
_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^)+(0.0360P)^2^+0.2770P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0694
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_reflns_number_gt                3024
_reflns_number_total             3504
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b00594_si_002.cif
_cod_data_source_block           g140929c
_cod_database_code               1554907
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         CHONPd
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H14A,H14B,H14C} of C14, All C(H,H) groups
 At 1.5 times of:
  {H8A,H8B,H8C} of C8, {H10A,H10B,H10C} of C10, {H12A,H12B,H12C} of C12
2.a Riding coordinates:
 C14(H14A,H14B,H14C)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              83032
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_olex2_submission_special_instructions 'No special instructions were received'