Cooperative benzylic–oxyallylic stabilized cations: regioselective construction of α-quaternary centers in ketone-derived compounds
Dange, Nitin S.; Stepherson, Jacob R.; Ayala, Caitlan E.; Fronczek, Frank R.; Kartika, Rendy; Chem. Sci. 6 (2015) 6312–; doi:10.1039/C5SC01914A

data_1529264
_publ_section_title
;
 Cooperative benzylic--oxyallylic stabilized cations: regioselective
 construction of \a-quaternary centers in ketone-derived compounds
;
_journal_issue                   11
_journal_name_full               'Chem. Sci.'
_journal_page_first              6312
_journal_paper_doi               10.1039/C5SC01914A
_journal_volume                  6
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C23 H23 N O3'
_chemical_formula_sum            'C23 H23 N O3'
_chemical_formula_weight         361.42
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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_creation_method           SHELXL-97
_audit_update_record
;
2015-04-01 deposited with the CCDC.
2015-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2261(3)
_cell_length_b                   13.4245(5)
_cell_length_c                   18.9990(9)
_cell_measurement_reflns_used    7072
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      60.92
_cell_measurement_theta_min      4.03
_cell_volume                     1843.03(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(5)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'QUAZAR multilayer optics'
_diffrn_radiation_source         'I\mS microfocus'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_av_sigmaI/netI    0.0498
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18058
_diffrn_reflns_theta_full        61.22
_diffrn_reflns_theta_max         61.22
_diffrn_reflns_theta_min         4.03
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_T_max  0.9864
_exptl_absorpt_correction_T_min  0.8372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane/dichloromethane'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details '1174 Friedel pairs (Flack, 1983) '
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         2831
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0523
_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^)+(0.0357P)^2^+0.8243P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1215
_reflns_number_gt                2333
_reflns_number_total             2831
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c5sc01914a2.cif
_cod_data_source_block           NSD-1183-F1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 1529260--1529265.cif.
;
_cod_original_sg_symbol_Hall     'P 2ac 2ab '
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               1529264