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_1553138
_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         'C17 H18 N2 O3'
_chemical_formula_sum            'C17 H18 N2 O3'
_chemical_formula_weight         298.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-10-11
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2014-10-21 deposited with the CCDC.
2015-06-03 downloaded from the CCDC.
;
_cell_angle_alpha                104.655(8)
_cell_angle_beta                 94.121(9)
_cell_angle_gamma                91.668(10)
_cell_formula_units_Z            2
_cell_length_a                   6.8879(9)
_cell_length_b                   8.2820(9)
_cell_length_c                   14.4023(10)
_cell_measurement_reflns_used    1393
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      25.9010
_cell_measurement_theta_min      3.4030
_cell_volume                     791.85(15)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -39.00   46.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885  -77.0000  -87.0000 85

  2 omega  -10.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885   77.0000   37.0000 100

  3 omega  -14.00   20.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.2104  -99.0000   60.0000 34

  4 omega  -20.00    9.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.2104  -99.0000 -180.0000 29

  5 omega  -51.00   45.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885  -37.0000  120.0000 96

  6 omega   36.00   62.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885  178.0000  -90.0000 26

  7 omega  -53.00   13.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7885  -37.0000    0.0000 66
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0414562000
_diffrn_orient_matrix_UB_12      -0.0223360000
_diffrn_orient_matrix_UB_13      0.0389338000
_diffrn_orient_matrix_UB_21      -0.0942368000
_diffrn_orient_matrix_UB_22      0.0132509000
_diffrn_orient_matrix_UB_23      -0.0191225000
_diffrn_orient_matrix_UB_31      -0.0090604000
_diffrn_orient_matrix_UB_32      -0.0846744000
_diffrn_orient_matrix_UB_33      -0.0269162000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6560
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         2.97
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99266
_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    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.036
_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     202
_refine_ls_number_reflns         3249
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0580P)^2^+0.0864P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1377
_reflns_number_gt                2128
_reflns_number_total             3249
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5qo00120j2.cif
_cod_data_source_block           201410198
_cod_database_code               1553138
_chemical_oxdiff_formula         C20H20N4O4
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C9(H9), C10(H10), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C17(H17A,H17B,H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'