Synthesis of Functionalized Azacalix[1]arene[3]pyridine Macrocycles from Cu(II)-Mediated Direct Amination Reactions of Arene through High Valent Arylcopper(III) Intermediates.
Liu, Yang; Zhang, Qian; Guo, Qing-Hui; Wang, Mei-Xiang; The Journal of organic chemistry 81 (2016) 10404–10410; doi:10.1021/acs.joc.6b01448

data_4037091
_publ_section_title
;
 Synthesis of Functionalized Azacalix[1]arene[3]pyridine Macrocycles from
 Cu(II)-Mediated Direct Amination Reactions of Arene through High Valent
 Arylcopper(III) Intermediates.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10404
_journal_page_last               10410
_journal_paper_doi               10.1021/acs.joc.6b01448
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C26 H25 F3 N8 O2 S, H2 O'
_chemical_formula_sum            'C26 H27 F3 N8 O3 S'
_chemical_formula_weight         588.61
_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   mixed
_audit_creation_date             2016-05-25
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                91.555(2)
_cell_angle_beta                 105.460(4)
_cell_angle_gamma                108.834(3)
_cell_formula_units_Z            2
_cell_length_a                   10.074(3)
_cell_length_b                   11.434(3)
_cell_length_c                   12.631(4)
_cell_measurement_reflns_used    4335
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4853
_cell_measurement_theta_min      2.2326
_cell_volume                     1316.9(7)
_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 0.986
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 40.0632
	          2theta: -20.1027
scan:
	Number of images: 354
	           Slice: -110.0000 - 67.0000
	     Image width: 0.5000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 40.0632
	          2theta: -20.1027
scan:
	Number of images: 242
	           Slice: -99.7500 - 21.2500
	     Image width: 0.5000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 40.0632
	          2theta: -20.1027
;
_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      -0.0302
_diffrn_orient_matrix_UB_12      -0.1001
_diffrn_orient_matrix_UB_13      0.0329
_diffrn_orient_matrix_UB_21      0.0301
_diffrn_orient_matrix_UB_22      -0.0639
_diffrn_orient_matrix_UB_23      -0.0606
_diffrn_orient_matrix_UB_31      0.0618
_diffrn_orient_matrix_UB_32      -0.0298
_diffrn_orient_matrix_UB_33      0.0463
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14441
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         1.686
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.81731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_description       block
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.87
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.903
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         5943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0608
_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^)+(0.0888P)^2^+0.9457P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1683
_refine_ls_wR_factor_ref         0.1708
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5614
_reflns_number_total             5943
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01448_si_001.cif
_cod_data_source_block           y
_cod_original_cell_volume        1317.0(7)
_cod_database_code               4037091
_diffrn_number_total             5947
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Riding coordinates:
 O3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N8(H8), C3(H3), C4(H4), C5(H5), C8(H8A), C9(H9), C10(H10), C13(H13), C14(H14),
  C15(H15), C18(H18), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C)
;
_shelx_res_checksum              37494
_shelx_hkl_checksum              21740
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'