Chemo- and regioselective click reactions through nickel-catalyzed azide-alkyne cycloaddition.
Kim, Woo Gyum; Baek, Seung-Yeol; Jeong, Seo Yeong; Nam, Dongsik; Jeon, Ji Hwan; Choe, Wonyoung; Baik, Mu-Hyun; Hong, Sung You; Organic & biomolecular chemistry 18 (2020) 3374–3381; doi:10.1039/d0ob00579g

data_7157466
_publ_section_title
;
 Chemo- and regioselective click reactions through nickel-catalyzed
 azide-alkyne cycloaddition.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3374
_journal_page_last               3381
_journal_paper_doi               10.1039/d0ob00579g
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C16 H11 N5 O2'
_chemical_formula_weight         305.30
_chemical_name_systematic        5ad
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_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
_audit_update_record
;
2019-12-05 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.83(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.1117(14)
_cell_length_b                   14.251(3)
_cell_length_c                   7.5497(15)
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_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.468
_cell_measurement_theta_min      3.115
_cell_volume                     746.0(3)
_computing_cell_refinement       'Rigaku Rapid Auto'
_computing_data_collection       'Rigaku Rapid Auto'
_computing_data_reduction        'Rigaku Rapid Auto'
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_computing_structure_solution    SHELXS
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_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'imaging plate'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7109
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_min         3.115
_diffrn_source                   'fine-focus sealed tube'
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_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Rigaku Rapid Auto'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       Block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.720
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.103
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.022
_refine_ls_abs_structure_details
;
 Flack x determined using 888 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3389
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0306P)^2^+0.0435P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0777
_reflns_Friedel_coverage         0.918
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                2490
_reflns_number_total             3389
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00579g2.cif
_cod_data_source_block           P21_a
_cod_depositor_comments
'Adding full bibliography for 7157466--7157469.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7157466
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              21236