Asymmetric N-Heterocyclic Carbene (NHC)-Catalyzed Annulation of Modified Enals with Enolizable Aldehydes
Yetra, Santhivardhana Reddy; Kaicharla, Trinadh; Kunte, Sunita S.; Gonnade, Rajesh G.; Biju, Akkattu T.; Organic Letters 15 (2013) 5202–; doi:10.1021/ol4026155

data_1512587
_publ_section_title
;
 Asymmetric N-Heterocyclic Carbene (NHC)-Catalyzed Annulation of Modified
 Enals with Enolizable Aldehydes
;
_journal_issue                   20
_journal_name_full               'Organic Letters'
_journal_page_first              5202
_journal_paper_doi               10.1021/ol4026155
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H15 Br O3'
_chemical_formula_sum            'C18 H15 Br O3'
_chemical_formula_weight         359.21
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.666(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.2782(7)
_cell_length_b                   9.3617(12)
_cell_length_c                   13.9272(17)
_cell_measurement_reflns_used    2149
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      20.60
_cell_measurement_theta_min      2.64
_cell_volume                     804.42(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'Bruker APEX-II CCD'
_diffrn_measurement_device_type  'CCD AREA DETECTOR'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0866
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7532
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.64
_exptl_absorpt_coefficient_mu    2.564
_exptl_absorpt_correction_T_max  0.7484
_exptl_absorpt_correction_T_min  0.4195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'sadabs (Bruker, 2006)'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PRISM
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.012(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3230
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.943
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0416
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0302P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.1007
_reflns_number_gt                1969
_reflns_number_total             3230
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol4026155_si_002.cif
_cod_data_source_block           svr_5d_77n
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1512587