A Click Chemistry Approach to 5,5'-Disubstituted-3,3'-Bisisoxazoles from Dichloroglyoxime and Alkynes: Luminescent Organometallic Iridium and Rhenium Bisisoxazole Complexes
Phillip L. van der Peet; Timothy U. Connell; Christian Gunawan; Jonathan M. White; Paul S. Donnelly; Spencer J. Williams; Journal of Organic Chemistry 78 (2013) 7298–7304; doi:10.1021/jo4008755

data_4028426
_publ_section_title
;
 A Click Chemistry Approach to 5,5'-Disubstituted-3,3'-Bisisoxazoles from
 Dichloroglyoxime and Alkynes: Luminescent Organometallic Iridium and
 Rhenium Bisisoxazole Complexes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7298
_journal_page_last               7304
_journal_paper_doi               10.1021/jo4008755
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C18 H12 N2 O2'
_chemical_formula_weight         288.30
_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                98.920(3)
_cell_angle_beta                 91.029(3)
_cell_angle_gamma                96.137(3)
_cell_formula_units_Z            2
_cell_length_a                   5.8521(2)
_cell_length_b                   8.9267(3)
_cell_length_c                   13.1255(5)
_cell_measurement_reflns_used    6798
_cell_measurement_temperature    130.0(2)
_cell_measurement_theta_max      73.8392
_cell_measurement_theta_min      3.4077
_cell_volume                     673.08(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      130.0(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) x-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0104
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9255
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         67.50
_diffrn_reflns_theta_min         3.41
_exptl_absorpt_coefficient_mu    0.767
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.5845
_exptl_crystal_size_mid          0.2361
_exptl_crystal_size_min          0.0853
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2418
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0324
_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^)+(0.0487P)^2^+0.1935P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0878
_reflns_number_gt                2323
_reflns_number_total             2418
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4008755_si_003.cif
_cod_data_source_block           shelxl
_cod_database_code               4028426