Palladium-catalyzed direct ortho C‒O bond construction of azoxybenzenes with carboxylic acids and alcohols
Zhang, Duo; Cui, Xiuling; Yang, Fangfang; Zhang, Qianqian; Zhu, Yu; Wu, Yangjie; Organic Chemistry Frontiers 2 (2015) 951–; doi:10.1039/C5QO00120J

data_1553137
_publ_section_title
;
 Palladium-catalyzed direct ortho C--O bond construction of azoxybenzenes
 with carboxylic acids and alcohols
;
_journal_issue                   8
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              951
_journal_paper_doi               10.1039/C5QO00120J
_journal_volume                  2
_journal_year                    2015
_chemical_formula_moiety         'C28 H21 F3 N4 O6 Pd2'
_chemical_formula_sum            'C28 H21 F3 N4 O6 Pd2'
_chemical_formula_weight         779.29
_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   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-09-29
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2014-09-30 deposited with the CCDC.
2015-06-03 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 105.969(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.4863(4)
_cell_length_b                   17.2032(5)
_cell_length_c                   11.5651(5)
_cell_measurement_reflns_used    3752
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      27.1690
_cell_measurement_theta_min      3.5460
_cell_volume                     2770.93(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -13.00   13.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1323  -99.0000 -150.0000 26

  2 omega   65.00   95.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7104  178.0000  -90.0000 30

  3 omega   64.00   96.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7104  178.0000 -180.0000 32

  4 omega  -43.00   91.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7104    0.0000  150.0000 134

  5 omega  -53.00  -28.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7104  -37.0000  -30.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0250054000
_diffrn_orient_matrix_UB_12      0.0355509000
_diffrn_orient_matrix_UB_13      -0.0162596000
_diffrn_orient_matrix_UB_21      0.0062682000
_diffrn_orient_matrix_UB_22      0.0086849000
_diffrn_orient_matrix_UB_23      0.0616507000
_diffrn_orient_matrix_UB_31      0.0439258000
_diffrn_orient_matrix_UB_32      0.0189731000
_diffrn_orient_matrix_UB_33      0.0022883000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12566
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.89
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.369
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.868
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.167
_refine_diff_density_min         -0.953
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         5658
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0518
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0739P)^2^+3.7033P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1342
_refine_ls_wR_factor_ref         0.1466
_reflns_number_gt                4346
_reflns_number_total             5658
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5qo00120j2.cif
_cod_data_source_block           201409196a
_cod_original_cell_volume        2770.92(17)
_cod_database_code               1553137
_chemical_oxdiff_formula         C20H20N4O4Pd1F3
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C28, F1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 F2, C28
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C28, F3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C27, O6
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C16(H16), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23),
  C24(H24)
3.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_olex2_submission_special_instructions 'No special instructions were received'