An asymmetric vinylogous Mukaiyama-Michael reaction of α,β-unsaturated 2-acyl imidazoles catalyzed by chiral Sc(iii)- or Er(iii)-pybox complexes.
Rout, Subhrajit; Das, Arko; Singh, Vinod K.; Chemical communications (Cambridge, England) 53 (2017) 5143–5146; doi:10.1039/c7cc01763d

data_7119962
_publ_section_title
;
 An asymmetric vinylogous Mukaiyama-Michael reaction of \a,\b-unsaturated
 2-acyl imidazoles catalyzed by chiral Sc(iii)- or Er(iii)-pybox
 complexes.
;
_journal_issue                   37
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5143
_journal_page_last               5146
_journal_paper_doi               10.1039/c7cc01763d
_journal_volume                  53
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C21 H17 Br N2 O4'
_chemical_formula_sum            'C21 H17 Br N2 O4'
_chemical_formula_weight         441.27
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-01-02
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2017-01-10 deposited with the CCDC.
2017-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.487(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.610(5)
_cell_length_b                   5.974(5)
_cell_length_c                   12.888(5)
_cell_measurement_reflns_used    8036
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.08
_cell_measurement_theta_min      2.67
_cell_volume                     931.0(9)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10915
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.117
_diffrn_reflns_theta_max         25.117
_diffrn_reflns_theta_min         2.670
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.239
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6005
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1315 before and 0.0744 after correction.
The Ratio of minimum to maximum transmission is 0.8058.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1249 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.076(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3246
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0242
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0191P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0551
_refine_ls_wR_factor_ref         0.0560
_reflns_Friedel_coverage         0.779
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                3042
_reflns_number_total             3246
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc01763d2.cif
_cod_data_source_block           7d
_cod_depositor_comments
'Adding full bibliography for 7119962--7119964.cif.'
_cod_database_code               7119962
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20),
 C24(H24), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_shelx_shelxl_version_number     2016/4
_olex2_submission_special_instructions 'No special instructions were received'