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_1529262
_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_formula_moiety         'C22 H23 N O2'
_chemical_formula_sum            'C22 H23 N O2'
_chemical_formula_weight         333.41
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 91.974(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0542(10)
_cell_length_b                   15.9871(11)
_cell_length_c                   7.7187(4)
_cell_measurement_reflns_used    3184
_cell_measurement_temperature    90.0(5)
_cell_measurement_theta_max      61.15
_cell_measurement_theta_min      3.15
_cell_volume                     1733.25(19)
_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 0.952
_diffrn_measured_fraction_theta_max 0.952
_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  0.0816
_diffrn_reflns_av_sigmaI/netI    0.0640
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            13157
_diffrn_reflns_theta_full        61.15
_diffrn_reflns_theta_max         61.15
_diffrn_reflns_theta_min         3.15
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_correction_T_min  0.6184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS (Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane/dichloromethane'
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2537
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0723
_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^)+(0.1411P)^2^+0.3725P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1985
_refine_ls_wR_factor_ref         0.2098
_reflns_number_gt                1965
_reflns_number_total             2537
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c5sc01914a2.cif
_cod_data_source_block           NSD-1131
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 2ybc '
_cod_original_sg_symbol_H-M      'P 21/c  '
_cod_database_code               1529262