Nickel-Catalyzed Azide-Alkyne Cycloaddition To Access 1,5-Disubstituted 1,2,3-Triazoles in Air and Water.
Kim, Woo Gyum; Kang, Mi Eun; Lee, Jae Bin; Jeon, Min Ho; Lee, Sungmin; Lee, Jungha; Choi, Bongseo; Cal, Pedro M. S. D.; Kang, Sebyung; Kee, Jung-Min; Bernardes, Gonçalo J L; Rohde, Jan-Uwe; Choe, Wonyoung; Hong, Sung You; Journal of the American Chemical Society 139 (2017) 12121–12124; doi:10.1021/jacs.7b06338

data_4131523
_publ_section_title
;
 Nickel-Catalyzed Azide-Alkyne Cycloaddition To Access 1,5-Disubstituted
 1,2,3-Triazoles in Air and Water.
;
_journal_issue                   35
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12121
_journal_page_last               12124
_journal_paper_doi               10.1021/jacs.7b06338
_journal_volume                  139
_journal_year                    2017
_chemical_formula_sum            'C15 H12 N4 O2'
_chemical_formula_weight         280.29
_chemical_name_common            GD-5
_chemical_name_systematic        GD-5
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 99.74(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.8000(14)
_cell_length_b                   11.502(2)
_cell_length_c                   8.4630(17)
_cell_measurement_reflns_used    4332
_cell_measurement_temperature    123
_cell_measurement_theta_max      31.490
_cell_measurement_theta_min      2.442
_cell_volume                     652.4(2)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      123
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1151
_diffrn_reflns_av_unetI/netI     0.1160
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7695
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.490
_diffrn_reflns_theta_min         2.442
_exptl_absorpt_coefficient_mu    0.099
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       needle
_exptl_crystal_F_000             123
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.751
_refine_diff_density_rms         0.154
_refine_ls_abs_structure_details
;
 Flack x determined using 1560 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4282
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.153
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0628
_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^)+(0.0898P)^2^+0.1115P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1664
_refine_ls_wR_factor_ref         0.1726
_reflns_Friedel_coverage         0.906
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                3946
_reflns_number_total             4282
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b06338_si_002.cif
_cod_data_source_block           P21_a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4131523
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              53072
_shelx_hkl_checksum              35049