N-Heterocyclic carbene-catalyzed desymmetrization of functionalized 1,4-dienes via Stetter Reaction
Qiqiao Lin; Yuanzhen Li; Deb Kumar Das; Guoxiang Zhang; Zhifei Zhao; Shuang Yang; Xinqiang Fang; Chem.Commun. 52 (2016) 6459–; doi:

data_7119098
_publ_section_title
;
 N-Heterocyclic carbene-catalyzed desymmetrization of functionalized
 1,4-dienes via Stetter Reaction
;
_journal_name_full               Chem.Commun.
_journal_page_first              6459
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H38 O3'
_chemical_formula_sum            'C27 H38 O3'
_chemical_formula_weight         410.57
_chemical_name_systematic
'(2S,3S)-3,7-dimethyl-2-(5-methyl-2-oxohexyl)-3- ((E)-6-methyl-3-oxohept-1-en-1-yl)-3,4-dihydronaphthalen-1(2H)-one'
_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     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cc1k8w0q
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2016-04-10 deposited with the CCDC.
2016-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.058(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.8458(3)
_cell_length_b                   12.3784(6)
_cell_length_c                   16.7657(12)
_cell_measurement_reflns_used    2334
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.9760
_cell_measurement_theta_min      4.4450
_cell_volume                     1201.22(12)
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2002)'
_computing_data_collection       'CrystalClear (Rigaku Corp., 2002)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2002)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3503
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4524
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.388
_diffrn_reflns_theta_min         4.456
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.560
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sphere (Rigaku CrystalClear)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.135
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             448
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   1.1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3234
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0761P)^2^+0.1734P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1185
_reflns_Friedel_coverage         0.912
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                3024
_reflns_number_total             3234
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc01011c2.cif
_cod_data_source_block           lqq
_cod_original_cell_volume        1201.23(12)
_cod_database_code               7119098
_shelxl_version_number           2014/6
_shelx_res_checksum              27818
_solvent_exptl_crystal_recrystallization_method
'ethyl acetate and diethyl ether'