Pd(II)-catalyzed coupling of C-H bonds of carboxamides with iodoazobenzenes toward modified azobenzenes.
Suwasia, Sonam; Venkataramani, Sugumar; Babu, Srinivasarao Arulananda; Organic & biomolecular chemistry 21 (2023) 1793–1813; doi:10.1039/d2ob02322a

data_7159115
_publ_section_title
;
 Pd(II)-catalyzed coupling of C-H bonds of carboxamides with
 iodoazobenzenes toward modified azobenzenes.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1793
_journal_page_last               1813
_journal_paper_doi               10.1039/d2ob02322a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C30 H24 N4 O'
_chemical_formula_sum            'C30 H24 N4 O'
_chemical_formula_weight         456.53
_chemical_name_systematic        C30H24N4O
_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     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
;
2022-12-27 deposited with the CCDC.	2023-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.917(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.231(2)
_cell_length_b                   8.7746(10)
_cell_length_c                   18.051(3)
_cell_measurement_reflns_used    1169
_cell_measurement_temperature    298.0
_cell_measurement_theta_max      18.9390
_cell_measurement_theta_min      2.6170
_cell_volume                     2360.4(6)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.931
_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    -69.00 120.00   0.30    5.00    --   29.89  54.00-180.00  630
  2  \w    -69.00 120.00   0.30    5.00    --   29.89  54.00-150.00  630
  3  \w    -69.00  27.00   0.30    5.00    --   29.89  54.00   0.00  320
;
_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      0.0288347000
_diffrn_orient_matrix_UB_12      -0.0274403000
_diffrn_orient_matrix_UB_13      0.0332794000
_diffrn_orient_matrix_UB_21      -0.0352100000
_diffrn_orient_matrix_UB_22      0.0076511000
_diffrn_orient_matrix_UB_23      0.0200910000
_diffrn_orient_matrix_UB_31      -0.0139604000
_diffrn_orient_matrix_UB_32      -0.0756228000
_diffrn_orient_matrix_UB_33      -0.0100710000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0963
_diffrn_reflns_av_unetI/netI     0.1272
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27642
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.867
_diffrn_reflns_theta_min         2.592
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29096
_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            'clear dark brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         8213
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.3211
_refine_ls_R_factor_gt           0.1101
_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^)+(0.1863P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2698
_refine_ls_wR_factor_ref         0.4230
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1931
_reflns_number_total             8213
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02322a2.cif
_cod_data_source_block           ss_305
_cod_depositor_comments          'Adding full bibliography for 7159115.cif.'
_cod_original_cell_volume        2360.5(6)
_cod_database_code               7159115
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3A)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C23(H23), C14(H14), C15(H15), C25(H25), C9(H9), C28(H28), C26(H26),
 C24(H24), C11(H11), C27(H27), C12(H12), C17(H17), C5(H5), C21(H21), C7(H7),
 C18(H18), C20(H20), C19(H19), C8(H8), C6(H6)
;
_shelx_res_checksum              85073
_olex2_submission_original_sample_id 'ss 305'
_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 1.867
_oxdiff_exptl_absorpt_empirical_full_min 0.535