Synthesis and Computational Analysis of Densely Functionalized Triazoles Using o-Nitrophenylalkynes
Melissa L. McIntosh; Ryne C. Johnston; Ommidala Pattawong; Bradley O. Ashburn; Michael R. Naffziger; Paul Ha-Yeon Cheong; Rich G. Carter; Journal of Organic Chemistry 77 (2012) 1101–1112; doi:10.1021/jo202467k

data_4026911
_publ_section_title
;
 Synthesis and Computational Analysis of Densely Functionalized Triazoles
 Using o-Nitrophenylalkynes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1101
_journal_page_last               1112
_journal_paper_doi               10.1021/jo202467k
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C23 H18 N4 O4'
_chemical_formula_weight         414.41
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXLTL
_cell_angle_alpha                90.00
_cell_angle_beta                 92.5030(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3017(7)
_cell_length_b                   9.7642(7)
_cell_length_c                   21.9140(16)
_cell_measurement_reflns_used    7340
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.25
_cell_measurement_theta_min      2.80
_cell_volume                     1988.4(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Apex CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            21787
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9865
_exptl_absorpt_correction_T_min  0.9732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         4334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0494P)^2^+0.6525P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.1003
_reflns_number_gt                3777
_reflns_number_total             4334
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202467k_si_005.cif
_cod_data_source_block           rc66
_cod_database_code               4026911