Pd-catalyzed selective N(3)-ortho C–H arylation of 1,4-disubstituted 1,2,3-triazoles
Zhao, Fen; Liu, Yaowen; Yang, Shu; Xie, Kai; Jiang, Yubo; Organic Chemistry Frontiers 4 (2017) 1112–; doi:10.1039/C6QO00834H

data_1553633
_publ_section_title
;
 Pd-catalyzed selective N(3)-ortho C--H arylation of 1,4-disubstituted
 1,2,3-triazoles
;
_journal_issue                   6
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1112
_journal_paper_doi               10.1039/C6QO00834H
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C29 H25 N3'
_chemical_formula_sum            'C29 H25 N3'
_chemical_formula_weight         415.52
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-10-21
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2016-10-23 deposited with the CCDC.
2017-02-22 downloaded from the CCDC.
;
_cell_angle_alpha                100.063(4)
_cell_angle_beta                 91.086(4)
_cell_angle_gamma                92.460(4)
_cell_formula_units_Z            2
_cell_length_a                   5.768(2)
_cell_length_b                   9.924(4)
_cell_length_c                   20.463(7)
_cell_measurement_reflns_used    2936
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.925
_cell_measurement_theta_min      2.474
_cell_volume                     1151.8(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         2.474
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4674
_refine_ls_number_restraints     76
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0457
_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^)+(0.0598P)^2^+0.1412P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1290
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3305
_reflns_number_total             4674
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00834h1.cif
_cod_data_source_block           ybm_0m
_cod_database_code               1553633
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C24-C29
 1.39 with sigma of 0.001
3. Rigid body (RIGU) restrains
 C19, C20
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 H22B, C24, C25, C25A, C26, C26A, C27, C28, C28A, C29, C29A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C25A)=Sof(H25A)=Sof(C26A)=Sof(H26A)=Sof(H27A)=Sof(C28A)=Sof(H28A)=
 Sof(C29A)=Sof(H29A)=1-FVAR(1)
 Sof(C25)=Sof(H25)=Sof(C26)=Sof(H26)=Sof(H27)=Sof(C28)=Sof(H28)=Sof(C29)=
 Sof(H29)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13), C14(H14),
 C17(H17), C18(H18), C20(H20), C21(H21), C25(H25), C25A(H25A), C26(H26),
 C26A(H26A), C27(H27), C27(H27A), C28(H28), C28A(H28A), C29(H29), C29A(H29A)
5.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              73720
_shelx_hkl_checksum              42386
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'