Enantioselective Synthesis of Chromanones Bearing Quaternary Substituted Stereocenters Catalyzed by (1R)-Camphor-Derived N-Heterocyclic Carbenes.
Rafiński, Zbigniew; Kozakiewicz, Anna; The Journal of organic chemistry 80 (2015) 7468–7476; doi:10.1021/acs.joc.5b01029

data_4031308
_publ_section_title
;
 Enantioselective Synthesis of Chromanones Bearing Quaternary Substituted
 Stereocenters Catalyzed by (1R)-Camphor-Derived N-Heterocyclic Carbenes.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7468
_journal_page_last               7476
_journal_paper_doi               10.1021/acs.joc.5b01029
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H24 B F4 N3 O'
_chemical_formula_sum            'C19 H24 B F4 N3 O'
_chemical_formula_weight         397.22
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.44(3)
_cell_angle_beta                 96.09(3)
_cell_angle_gamma                110.21(3)
_cell_formula_units_Z            2
_cell_length_a                   6.8740(10)
_cell_length_b                   7.0570(10)
_cell_length_c                   21.567(4)
_cell_measurement_reflns_used    13020
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0.9960
_cell_measurement_theta_min      0.9510
_cell_volume                     966.5(4)
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2000)'
_computing_data_collection       'CrysAlis (Oxford Diffraction, 2000)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2000)'
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.2564
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.888
_diffrn_measurement_device_type  'Oxford Sapphire CCD'
_diffrn_measurement_method       \q/2\q
_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  0.0519
_diffrn_reflns_av_sigmaI/netI    0.0863
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6530
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         2.88
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9960
_exptl_absorpt_correction_T_min  0.9510
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Oxford Diffraction CrysAlis'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -4(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         5265
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1616
_refine_ls_R_factor_gt           0.0942
_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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2468
_refine_ls_wR_factor_ref         0.3040
_reflns_number_gt                2775
_reflns_number_total             5265
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b01029_si_001.cif
_cod_data_source_block           zr11
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/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 4031308.cif.
;
_cod_original_cell_volume        966.5(3)
_cod_original_sg_symbol_H-M      P1
_cod_database_code               4031308