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_1555812
_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     iterative
_audit_creation_date             2015-07-01
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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_cell_angle_alpha                90
_cell_angle_beta                 101.794(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.2960(12)
_cell_length_b                   10.5965(7)
_cell_length_c                   15.8781(12)
_cell_measurement_reflns_used    1837
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      22.9010
_cell_measurement_theta_min      3.7070
_cell_volume                     2848.7(4)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_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
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
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_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega  -18.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5454   57.0000  150.0000 101

  2 omega   35.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5454  178.0000   30.0000 63
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0269315000
_diffrn_orient_matrix_UB_12      -0.0352970000
_diffrn_orient_matrix_UB_13      -0.0308195000
_diffrn_orient_matrix_UB_21      0.0145508000
_diffrn_orient_matrix_UB_22      -0.0566839000
_diffrn_orient_matrix_UB_23      0.0212457000
_diffrn_orient_matrix_UB_31      -0.0285949000
_diffrn_orient_matrix_UB_32      0.0044189000
_diffrn_orient_matrix_UB_33      0.0261378000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0834
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10968
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.175
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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_colour
;
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_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description
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_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0057(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     384
_refine_ls_number_reflns         5582
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.1145
_refine_ls_R_factor_gt           0.0570
_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^)+(0.0415P)^2^+0.2348P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1386
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3302
_reflns_number_total             5582
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02530_si_003.cif
_cod_data_source_block           exp_5524
_cod_database_code               1555812
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         C35H31N7
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.992
_reflns_odcompleteness_completeness 99.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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:
 C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15),
 C16(H16), C20(H20), C21(H21), C22(H22), C27(H27), C28(H28), C29(H29), C31(H31),
  C32(H32), C33(H33), C34(H34)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C12(H12A,H12B,H12C), C18(H18A,H18B,H18C), C25(H25A,H25B,H25C)
;
_olex2_submission_special_instructions 'No special instructions were received'