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_4028428
_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            'C21 H12 Br N2 O5 Re'
_chemical_formula_weight         638.44
_chemical_name_systematic
;
 ?
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.155(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.8354(7)
_cell_length_b                   12.8132(4)
_cell_length_c                   7.0674(2)
_cell_measurement_reflns_used    3529
_cell_measurement_temperature    130.0(2)
_cell_measurement_theta_max      74.3146
_cell_measurement_theta_min      3.4465
_cell_volume                     1975.93(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      130.2(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_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  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7192
_diffrn_reflns_theta_full        74.37
_diffrn_reflns_theta_max         74.37
_diffrn_reflns_theta_min         4.00
_exptl_absorpt_coefficient_mu    14.730
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.146
_exptl_crystal_description       rod
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.2300
_exptl_crystal_size_mid          0.0737
_exptl_crystal_size_min          0.0329
_refine_diff_density_max         1.692
_refine_diff_density_min         -2.522
_refine_diff_density_rms         0.222
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         3882
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0431
_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^)+(0.0507P)^2^+25.1477P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1193
_reflns_number_gt                3586
_reflns_number_total             3882
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4008755_si_005.cif
_cod_data_source_block           shelxl
_cod_database_code               4028428