Rhodium(III)-Catalysed Carboxylate-Directed C-H Functionalizations of Isoxazoles with Alkynes
Yugandar , Somaraju; Nakamura, Hiroyuki; Chemical Communications  (2019) –; doi:10.1039/C9CC03283E

data_7123623
_publ_section_title
;
 Rhodium(III)-Catalysed Carboxylate-Directed C-H Functionalizations of
 Isoxazoles with Alkynes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC03283E
_journal_year                    2019
_chemical_formula_sum            'C24 H14 Cl N O3'
_chemical_formula_weight         399.81
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-09-29 deposited with the CCDC.    2019-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.014(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.1094(16)
_cell_length_b                   5.7150(8)
_cell_length_c                   15.077(2)
_cell_measurement_reflns_used    3581
_cell_measurement_temperature    90
_cell_measurement_theta_max      28.603
_cell_measurement_theta_min      2.827
_cell_volume                     893.6(2)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHELXle (Bruker AXS)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-2016 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0125
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5418
_diffrn_reflns_point_group_measured_fraction_full 0.934
_diffrn_reflns_point_group_measured_fraction_max 0.815
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.081
_diffrn_reflns_theta_min         1.447
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_description       prism
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.054
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1417 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3890
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0290
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0445P)^2^+0.1465P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0737
_refine_ls_wR_factor_ref         0.0746
_reflns_Friedel_coverage         0.635
_reflns_Friedel_fraction_full    0.856
_reflns_Friedel_fraction_max     0.700
_reflns_number_gt                3743
_reflns_number_total             3890
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc03283e2.cif
_cod_data_source_block           CRL37138_399_1_2m_a
_cod_database_code               7123623
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.893
_shelx_estimated_absorpt_t_max   0.987
_shelx_res_checksum              37767