Copper-Catalyzed Oxidative Cross-Dehydrogenative Coupling/Oxidative Cycloaddition: Synthesis of 4-Acyl-1,2,3-Triazoles.
Liu, Yi; Nie, Gang; Zhou, Zhongzhen; Jia, Lihui; Chen, Yunfeng; The Journal of organic chemistry 82 (2017) 9198–9203; doi:10.1021/acs.joc.7b01429

data_4032809
_publ_section_title
;
 Copper-Catalyzed Oxidative Cross-Dehydrogenative Coupling/Oxidative
 Cycloaddition: Synthesis of 4-Acyl-1,2,3-Triazoles.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9198
_journal_page_last               9203
_journal_paper_doi               10.1021/acs.joc.7b01429
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C16 H13 N3 O'
_chemical_formula_sum            'C16 H13 N3 O'
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_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2017-01-09
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_cell_angle_alpha                86.741(5)
_cell_angle_beta                 63.415(6)
_cell_angle_gamma                86.611(5)
_cell_formula_units_Z            4
_cell_length_a                   10.9510(7)
_cell_length_b                   11.4414(7)
_cell_length_c                   11.9203(7)
_cell_measurement_reflns_used    3243
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.0510
_cell_measurement_theta_min      2.6620
_cell_volume                     1332.53(16)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
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_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13123
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_min         2.570
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            WHITE
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             552
_refine_diff_density_max         0.177
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_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
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_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^)+(0.0493P)^2^+0.2247P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1308
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3577
_reflns_number_total             5218
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01429_si_002.cif
_cod_data_source_block           2
_cod_depositor_comments
;

2020-04-04
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        1332.53(15)
_cod_original_formula_moiety     '2(C16 H13 N3 O)'
_cod_original_formula_sum        'C32 H26 N6 O2'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     526.59
_cod_database_code               4032809
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Rigid bond restraints
 C13, C14
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
;
_shelx_res_checksum              61597
_shelx_hkl_checksum              50384
_olex2_submission_special_instructions 'No special instructions were received'