Pd(II)-catalyzed selective β-C-H functionalization of azobenzene carboxamides.
Padmavathi, Rayavarapu; Babu, Srinivasarao Arulananda; Organic & biomolecular chemistry 21 (2023) 2689–2694; doi:10.1039/d2ob02261c

data_7159085
_publ_section_title
;
 Pd(II)-catalyzed selective &#x3b2;-C-H functionalization of azobenzene
 carboxamides.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2689
_journal_page_last               2694
_journal_paper_doi               10.1039/d2ob02261c
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C20 H14 N2 O3'
_chemical_formula_sum            'C20 H14 N2 O3'
_chemical_formula_weight         330.33
_chemical_name_systematic        C20H14N2O3
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-12-13 deposited with the CCDC.	2023-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.588(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6384(9)
_cell_length_b                   19.8168(19)
_cell_length_c                   9.4404(11)
_cell_measurement_reflns_used    1215
_cell_measurement_temperature    298
_cell_measurement_theta_max      30.3850
_cell_measurement_theta_min      2.9830
_cell_volume                     1593.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -67.00 114.00   0.50   20.00    --   29.89  54.00-120.00  362
  2  \w     79.00 104.00   0.50   20.00    --   29.89  54.00  30.00   50
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0047301000
_diffrn_orient_matrix_UB_12      0.0080228000
_diffrn_orient_matrix_UB_13      0.0724192000
_diffrn_orient_matrix_UB_21      0.0419391000
_diffrn_orient_matrix_UB_22      -0.0298990000
_diffrn_orient_matrix_UB_23      0.0229929000
_diffrn_orient_matrix_UB_31      0.0717388000
_diffrn_orient_matrix_UB_32      0.0179729000
_diffrn_orient_matrix_UB_33      0.0059658000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5199
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.603
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic dark orange'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2799
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0507
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0767P)^2^+0.0825P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1634
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1782
_reflns_number_total             2799
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02261c2.cif
_cod_data_source_block           rp1338
_cod_depositor_comments          'Adding full bibliography for 7159085.cif.'
_cod_database_code               7159085
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.972
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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:
 C11(H11), C20(H20), C7(H7), C4(H4), C13(H13), C14(H14), C3(H3), C16(H16),
 C17(H17), C19(H19), C18(H18)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              48042
_olex2_submission_original_sample_id 'rp 1338'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.058
_oxdiff_exptl_absorpt_empirical_full_min 0.943