Catalytic Asymmetric [4+2]-Cycloaddition of Dienes with Aldehydes
Liu, Luping; Kim, Hyejin; Xie, Youwei; Farès, Christophe; Kaib, Philip S. J.; Goddard, Richard; List, Benjamin; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b08357

data_4126475
_publ_section_title
;
 Catalytic Asymmetric [4+2]-Cycloaddition of Dienes with Aldehydes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b08357
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H15 Br O'
_chemical_formula_sum            'C13 H15 Br O'
_chemical_formula_weight         267.16
_chemical_name_systematic
;
 (R)-2-(4-bromophenyl)-4,5-dimethyl-3,6-dihydro-2H-pyran
;
_chemical_properties_physical    heat-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                LIL-LB-836_10450
_audit_creation_date             2016-12-19
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.836(2)
_cell_length_b                   11.5511(9)
_cell_length_c                   15.3107(9)
_cell_measurement_reflns_used    71272
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.1
_cell_measurement_theta_min      2.6595
_cell_volume                     1209.0(4)
_computing_cell_refinement       'REVALCCD V. 1.6, 2008'
_computing_data_collection       'DATCOL (Bruker AXS, 2006)'
_computing_data_reduction        'REVALCCD V. 1.6, 2008'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 1997-2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 18.02
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker AXS Enraf-Nonius KappaCCD'
_diffrn_measurement_method       'CCD \f- and \w-scans'
_diffrn_radiation_monochromator  'Incoatec Helios focusing multilayer optics'
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            65284
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.119
_diffrn_reflns_theta_min         3.528
_exptl_absorpt_coefficient_mu    3.372
_exptl_absorpt_correction_T_max  0.75447
_exptl_absorpt_correction_T_min  0.51719
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent:  pentane'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1850 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.006(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         4595
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0220
_refine_ls_R_factor_gt           0.0203
_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^)+(0.0221P)^2^+0.3606P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0521
_refine_ls_wR_factor_ref         0.0530
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4427
_reflns_number_total             4595
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b08357_si_001.cif
_cod_data_source_block           3f
_cod_original_cell_volume        1208.9(4)
_cod_database_code               4126475
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.511
_shelx_estimated_absorpt_t_max   0.751
_shelx_res_checksum              33888
_shelx_hkl_checksum              66225