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_4026910
_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            'C16 H13 Cl N4 O2'
_chemical_formula_weight         328.75
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 113.436(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   30.931(6)
_cell_length_b                   7.4285(13)
_cell_length_c                   14.506(3)
_cell_measurement_reflns_used    2582
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.62
_cell_measurement_theta_min      2.82
_cell_volume                     3058.1(10)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector Bruker Apex'
_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  0.0404
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9853
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.44
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  0.9817
_exptl_absorpt_correction_T_min  0.9319
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_meas      0
_exptl_crystal_description       plate
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3342
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0505
_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^)+(0.0685P)^2^+2.9034P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1203
_refine_ls_wR_factor_ref         0.1331
_reflns_number_gt                2556
_reflns_number_total             3342
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202467k_si_004.cif
_cod_data_source_block           rc48
_cod_original_cell_volume        3058.1(9)
_cod_database_code               4026910