Efficient synthesis of oxazoles by dirhodium(II)-catalyzed reactions of styryl diazoacetate with oximes
Xinfang Xu; Peter Y. Zavalij; Wenhao Hu; Michael P. Doyle; Chem.Commun. 48 (2012) 11522–; doi:10.1039/c2cc36537e

data_7108614
_publ_section_title
;
 Efficient synthesis of oxazoles by dirhodium(II)-catalyzed reactions of
 styryl diazoacetate with oximes
;
_journal_name_full               Chem.Commun.
_journal_page_first              11522
_journal_paper_doi               10.1039/c2cc36537e
_journal_volume                  48
_journal_year                    2012
_chemical_formula_moiety         'C18 H14 Br N O2'
_chemical_formula_sum            'C18 H14 Br N O2'
_chemical_formula_weight         356.21
_chemical_name_common            'Xu XXU-NOH-Br'
_chemical_name_systematic
;
Xu XXU-NOH-Br
;
_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 & ZCIF'
_cell_angle_alpha                82.8208(11)
_cell_angle_beta                 77.3755(11)
_cell_angle_gamma                73.6561(12)
_cell_formula_units_Z            2
_cell_length_a                   7.0327(5)
_cell_length_b                   9.2545(7)
_cell_length_c                   12.4679(9)
_cell_measurement_reflns_used    7430
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.3
_cell_volume                     758.10(10)
_computing_cell_refinement       Apex2
_computing_data_collection       'Apex2 (Bruker, 2010)'
_computing_data_reduction        Apex2
_computing_molecular_graphics    'XSHEL (Bruker, 2004)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.333
_diffrn_detector_type            'Bruker Smart Apex II'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'three-circle diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_measurement_specimen_support 'MiTeGen loop'
_diffrn_orient_matrix_type       standard
_diffrn_orient_matrix_UB_11      0.0893684
_diffrn_orient_matrix_UB_12      0.0663216
_diffrn_orient_matrix_UB_13      0.0019759
_diffrn_orient_matrix_UB_21      -0.0560618
_diffrn_orient_matrix_UB_22      0.0107225
_diffrn_orient_matrix_UB_23      0.0803906
_diffrn_orient_matrix_UB_31      0.1080460
_diffrn_orient_matrix_UB_32      -0.0906916
_diffrn_orient_matrix_UB_33      0.0178988
_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  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0200
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10646
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.30
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    2.717
_exptl_absorpt_correction_T_max  0.762
_exptl_absorpt_correction_T_min  0.432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.240
_refine_diff_density_min         -1.011
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3467
_refine_ls_number_restraints     58
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0300
_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^)+(0.01P)^2^+1.074P], P=(max(Fo^2^,0)+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0643
_refine_ls_wR_factor_ref         0.0657
_reflns_number_gt                3246
_reflns_number_total             3467
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc36537e.txt
_cod_data_source_block           2301
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'refAll' changed to 'refall'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7108614