Catalytic hetero-ene reactions of 5-methyleneoxazolines: highly enantioselective synthesis of 2,5-disubstituted oxazole derivatives
Weiwei Luo; Jiannan Zhao; Chengkai Yin; Xiaohua Liu; Lili Lin; Xiaoming Feng; Chem.Commun. 50 (2014) 7524–; doi:10.1039/C4CC02809K

data_7114641
_publ_section_title
;
 Catalytic hetero-ene reactions of 5-methyleneoxazolines: highly
 enantioselective synthesis of 2,5-disubstituted oxazole derivatives
;
_journal_name_full               Chem.Commun.
_journal_page_first              7524
_journal_paper_doi               10.1039/C4CC02809K
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C18 H14 Br N O3'
_chemical_formula_sum            'C18 H14 Br N O3'
_chemical_formula_weight         372.21
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2013-11-04
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.961(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.3897(5)
_cell_length_b                   5.3882(2)
_cell_length_c                   13.3371(6)
_cell_measurement_reflns_used    1228
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.9720
_cell_measurement_theta_min      3.1840
_cell_volume                     782.90(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.9978
_diffrn_measured_fraction_theta_max 0.6810
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0484930000
_diffrn_orient_matrix_UB_12      -0.0446636000
_diffrn_orient_matrix_UB_13      0.0426230000
_diffrn_orient_matrix_UB_21      0.0058321000
_diffrn_orient_matrix_UB_22      0.1190502000
_diffrn_orient_matrix_UB_23      0.0236895000
_diffrn_orient_matrix_UB_31      -0.0430342000
_diffrn_orient_matrix_UB_32      -0.0342165000
_diffrn_orient_matrix_UB_33      0.0267018000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3827
_diffrn_reflns_point_group_measured_fraction_full 0.806
_diffrn_reflns_point_group_measured_fraction_max 0.804
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.365
_diffrn_reflns_theta_min         3.194
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.640
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 590 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.024(11)
_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     212
_refine_ls_number_reflns         2577
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0443
_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^)+(0.0312P)^2^+0.0087P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0880
_reflns_Friedel_coverage         0.450
_reflns_Friedel_fraction_full    0.566
_reflns_Friedel_fraction_max     0.561
_reflns_number_gt                2112
_reflns_number_total             2577
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc02809k2.cif
_cod_data_source_block           131104_s3_lww
_cod_database_code               7114641
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         c12h20n2o3br1
_shelx_estimated_absorpt_t_max   0.620
_shelx_estimated_absorpt_t_min   0.505
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C5(H5), C6(H6), C11(H11), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
;
_shelx_res_checksum              67369
_shelx_hkl_checksum              3324