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_1553136
_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         'C14 H14 N2 O3'
_chemical_formula_sum            'C14 H14 N2 O3'
_chemical_formula_weight         258.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-09-09
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2014-09-14 deposited with the CCDC.
2015-06-03 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.044(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.8276(3)
_cell_length_b                   8.4882(2)
_cell_length_c                   24.8068(7)
_cell_measurement_reflns_used    3558
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      71.7930
_cell_measurement_theta_min      3.4460
_cell_volume                     2700.60(12)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      291.15
_diffrn_detector_area_resol_mean 16.2312
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
  1 omega  -71.00  -32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  -90.0000 39

  2 omega  -70.00  -44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000   60.0000 26

  3 omega    2.00   40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -180.0000 38

  4 omega    3.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -120.0000 26

  5 omega   29.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -99.0000 -120.0000 69

  6 omega   -4.00   26.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -99.0000 -120.0000 30

  7 omega  -12.00   79.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -37.0000   90.0000 91

  8 omega   14.00   61.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000  -30.0000 47

  9 omega  -15.00   59.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -37.0000    0.0000 74

 10 omega   42.00   87.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000 -150.0000 45

 11 omega   40.00   89.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  120.0000 49

 12 omega   44.00   85.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   60.0000 41

 13 omega   46.00   84.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -60.0000 38

 14 omega   55.00   92.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   90.0000 37

 15 omega   64.00   90.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000    0.0000 26

 16 omega   96.00  154.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000 -120.0000 58

 17 omega   41.00   97.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -90.0000 56

 18 omega   63.00  174.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000    0.0000 -180.0000 111

 19 omega  -70.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -77.0000  -30.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0904818000
_diffrn_orient_matrix_UB_12      -0.1017072000
_diffrn_orient_matrix_UB_13      0.0222185000
_diffrn_orient_matrix_UB_21      -0.0125892000
_diffrn_orient_matrix_UB_22      0.0753109000
_diffrn_orient_matrix_UB_23      0.0560047000
_diffrn_orient_matrix_UB_31      -0.0779698000
_diffrn_orient_matrix_UB_32      -0.1301402000
_diffrn_orient_matrix_UB_33      0.0150723000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            10232
_diffrn_reflns_theta_full        72.43
_diffrn_reflns_theta_max         72.43
_diffrn_reflns_theta_min         3.45
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98598
_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    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         5224
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0478
_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^)+(0.0653P)^2^+0.2905P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1417
_reflns_number_gt                3823
_reflns_number_total             5224
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5qo00120j2.cif
_cod_data_source_block           201408170
_cod_original_cell_volume        2700.61(12)
_cod_database_code               1553136
_chemical_oxdiff_formula         C20H20N4O4
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C1'(H1'),
 C2'(H2'), C3'(H3'), C4'(H4'), C5'(H5'), C9'(H9'), C10'(H10'), C11'(H11')
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C13'(H13D,H13E,H13F), C14'(H14D,
 H14E,H14F)
;
_olex2_submission_special_instructions 'No special instructions were received'