Fused Polycyclic Compounds via Cycloaddition of 4-(1'-Cyclohexenyl)-5-iodo-1,2,3-triazoles with 4-Phenyl-1,2,4-triazoline-3,5-dione: The Importance of a Sacrificial Iodide Leaving Group
Heather A. Michaels; J. Tyler Simmons; Ronald J. Clark; Lei Zhu; Journal of Organic Chemistry 78 (2013) 5038–5044; doi:10.1021/jo400271j

data_4028223
_publ_section_title
;
 Fused Polycyclic Compounds via Cycloaddition of
 4-(1'-Cyclohexenyl)-5-iodo-1,2,3-triazoles with
 4-Phenyl-1,2,4-triazoline-3,5-dione: The Importance of a Sacrificial
 Iodide Leaving Group
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5038
_journal_page_last               5044
_journal_paper_doi               10.1021/jo400271j
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C23 H22 N6 O3'
_chemical_formula_sum            'C23 H22 N6 O3'
_chemical_formula_weight         430.47
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.113(4)
_cell_angle_beta                 101.220(4)
_cell_angle_gamma                91.799(4)
_cell_formula_units_Z            2
_cell_length_a                   6.713(2)
_cell_length_b                   11.072(3)
_cell_length_c                   14.727(5)
_cell_measurement_reflns_used    4317
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.26
_cell_measurement_theta_min      2.51
_cell_volume                     1061.0(6)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11582
_diffrn_reflns_theta_full        26.73
_diffrn_reflns_theta_max         26.73
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9929
_exptl_absorpt_correction_T_min  0.9726
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       thin
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4490
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0672P)^2^+0.3513P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1309
_reflns_number_gt                3640
_reflns_number_total             4490
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo400271j_si_001_1.cif
_cod_data_source_block           zhu134
_cod_original_cell_volume        1060.9(6)
_cod_original_sg_symbol_Hall     -P1
_cod_database_code               4028223