Functionalization of Azacalixaromatics by Cu(II)-Catalyzed Oxidative Cross-Coupling Reaction between the Arene C-H Bond and Boronic Acids.
Liu, Yang; Long, Chao; Zhao, Liang; Wang, Mei-Xiang; Organic letters 18 (2016) 5078–5081; doi:10.1021/acs.orglett.6b02530

data_1555811
_publ_section_title
;
 Functionalization of Azacalixaromatics by Cu(II)-Catalyzed Oxidative
 Cross-Coupling Reaction between the Arene C-H Bond and Boronic Acids.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5078
_journal_page_last               5081
_journal_paper_doi               10.1021/acs.orglett.6b02530
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C35 H31 N7'
_chemical_formula_sum            'C35 H31 N7'
_chemical_formula_weight         549.67
_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     direct
_audit_creation_date             2015-04-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 111.847(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.240(4)
_cell_length_b                   21.296(4)
_cell_length_c                   14.917(3)
_cell_measurement_reflns_used    14969
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4715
_cell_measurement_theta_min      1.4881
_cell_volume                     5673(2)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 45.1350
	          2theta: -19.9458
scan:
	Number of images: 240
	           Slice: -80.0000 - 40.0000
	     Image width: 0.5000
	        Exp time: 20.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 45.1350
	          2theta: -19.9458
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0603
_diffrn_orient_matrix_UB_12      0.0387
_diffrn_orient_matrix_UB_13      -0.0091
_diffrn_orient_matrix_UB_21      0.0209
_diffrn_orient_matrix_UB_22      0.0372
_diffrn_orient_matrix_UB_23      0.0197
_diffrn_orient_matrix_UB_31      -0.0006
_diffrn_orient_matrix_UB_32      0.0264
_diffrn_orient_matrix_UB_33      -0.0494
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            36936
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.731
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_description       block
_exptl_crystal_F_000             2320
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.234
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     765
_refine_ls_number_reflns         12944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.234
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0775
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0298P)^2^+2.6145P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1335
_refine_ls_wR_factor_ref         0.1403
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10971
_reflns_number_total             12944
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02530_si_002.cif
_cod_data_source_block           a
_cod_database_code               1555811
_diffrn_number_total             13313
_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:
 C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14),
 C15(H15), C18(H18), C19(H19), C20(H20), C23(H23), C24(H24), C25(H25), C27(H27),
  C28(H28), C29(H29), C30(H30), C2A(H2A), C3A(H3A), C4A(H4A), C8A(H8A),
 C9A(H9A), C10A(H10A), C13A(H13A), C14A(H14A), C15A(H15A), C18A(H18A),
 C19A(H19A), C20A(H20A), C23A(H23A), C24A(H24A), C25A(H25A), C27A(H27A),
 C28A(H28A), C29A(H29A), C30A(H30A)
2.b Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C35(H35A,H35B,
 H35C), C32A(H32D,H32E,H32F), C33A(H33D,H33E,H33F), C34A(H34D,H34E,H34F),
 C35A(H35D,H35E,H35F)
;
_shelx_res_checksum              97194
_shelx_hkl_checksum              54395
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'