Palladium(II)-catalyzed direct regioselectively oxidative acylation of azobenzenes with toluene derivatives.
Song, Hongyu; Chen, Dong; Pi, Chao; Cui, Xiuling; Wu, Yangjie; The Journal of organic chemistry 79 (2014) 2955–2962; doi:10.1021/jo5000219

data_4037607
_publ_section_title
;
 Palladium(II)-catalyzed direct regioselectively oxidative acylation of
 azobenzenes with toluene derivatives.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2955
_journal_page_last               2962
_journal_paper_doi               10.1021/jo5000219
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C26 H16 Cl2 N2 O2'
_chemical_formula_sum            'C26 H16 Cl2 N2 O2'
_chemical_formula_weight         459.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-09-06
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.746(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.2452(12)
_cell_length_b                   8.0381(5)
_cell_length_c                   12.3549(6)
_cell_measurement_reflns_used    1736
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      69.8820
_cell_measurement_theta_min      4.0330
_cell_volume                     2183.5(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega    1.00   26.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   90.0000 25

  2 omega   44.00   69.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   90.0000 25

  3 omega -111.00  -22.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -57.0000  -90.0000 89

  4 omega   -2.00   25.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000  -30.0000 27

  5 omega  -15.00   26.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000 -180.0000 41

  6 omega  -89.00  -63.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000 -146.0000   87.0000 26

  7 omega  -92.00  -13.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000    0.0000 79

  8 omega  -14.00   29.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   30.0000   60.0000 43

  9 omega  138.00  177.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000 -180.0000 39

 10 omega   52.00   82.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -60.0000 30

 11 omega   51.00   77.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -180.0000 26

 12 omega   42.00  103.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   30.0000 61

 13 omega   45.00   98.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000    0.0000 53

 14 omega   42.00   94.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  120.0000 52

 15 omega  137.00  176.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000 -120.0000 39

 16 omega   90.00  129.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000 -120.0000 39

 17 omega   40.00   88.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   60.0000 48

 18 omega   53.00  105.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000   90.0000 52

 19 omega   -4.00   42.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  -60.0000 46

 20 omega -113.00  -43.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000  120.0000 70

 21 omega   -4.00   98.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -99.0000  -90.0000 102
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0268807000
_diffrn_orient_matrix_UB_12      0.0658645000
_diffrn_orient_matrix_UB_13      0.0995367000
_diffrn_orient_matrix_UB_21      0.0645495000
_diffrn_orient_matrix_UB_22      0.0133046000
_diffrn_orient_matrix_UB_23      0.0654049000
_diffrn_orient_matrix_UB_31      0.0051102000
_diffrn_orient_matrix_UB_32      0.1794694000
_diffrn_orient_matrix_UB_33      -0.0414129000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0131
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4120
_diffrn_reflns_theta_full        67.05
_diffrn_reflns_theta_max         67.05
_diffrn_reflns_theta_min         4.02
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.891
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1955
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0505
_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^)+(0.0713P)^2^+1.1606P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1515
_reflns_number_gt                1490
_reflns_number_total             1955
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5000219_si_001.cif
_cod_data_source_block           201309133
_cod_database_code               4037607
_chemical_oxdiff_formula         C20H20N4O4Cl1
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13)
;