Copper-Catalyzed [3 + 2] Cycloaddition/Oxidation Reactions between Nitro-olefins and Organic Azides: Highly Regioselective Synthesis of NO2-Substituted 1,2,3-Triazoles.
Chen, Yunfeng; Nie, Gang; Zhang, Qi; Ma, Shan; Li, Huan; Hu, Qinquan; Organic letters 17 (2015) 1118–1121; doi:10.1021/ol503687w

data_1518747
_publ_section_title
;
 Copper-Catalyzed [3 + 2] Cycloaddition/Oxidation Reactions between
 Nitro-olefins and Organic Azides: Highly Regioselective Synthesis of
 NO2-Substituted 1,2,3-Triazoles.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1118
_journal_page_last               1121
_journal_paper_doi               10.1021/ol503687w
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C14 H9 Cl N4 O2'
_chemical_formula_weight         300.70
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_symmetry_space_group_name_Hall  '-P 1'
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_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_cell_angle_alpha                93.902(3)
_cell_angle_beta                 90.560(3)
_cell_angle_gamma                112.233(3)
_cell_formula_units_Z            6
_cell_length_a                   11.310(3)
_cell_length_b                   13.792(3)
_cell_length_c                   13.982(3)
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.71
_cell_measurement_theta_min      2.25
_cell_volume                     2012.7(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.934
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_R_equivalents  0.0491
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_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11596
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.46
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_T_max  0.9711
_exptl_absorpt_correction_T_min  0.9434
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             924
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.696
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     568
_refine_ls_number_reflns         6640
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0745
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1617P)^2^+1.7127P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2121
_refine_ls_wR_factor_ref         0.2337
_reflns_number_gt                5663
_reflns_number_total             6640
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol503687w_si_001.cif
_cod_data_source_block           mo_141008c_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

 Adding full bibliography for 1518747--1518748.cif.
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_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1518747