Reaction of Corey Ylide with α,β-Unsaturated Ketones: Tuning of Chemoselectivity toward Dihydrofuran Synthesis.
Chagarovsky, Alexey O.; Budynina, Ekaterina M.; Ivanova, Olga A.; Villemson, Elena V.; Rybakov, Victor B.; Trushkov, Igor V.; Melnikov, Mikhail Ya; Organic letters 16 (2014) 2830–2833; doi:10.1021/ol500877c

data_1516047
_publ_contact_author             'Dr Victor B. Rybakov'
_publ_section_title
;
 Reaction of Corey Ylide with \a,\b-Unsaturated Ketones: Tuning of
 Chemoselectivity toward Dihydrofuran Synthesis.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2830
_journal_page_last               2833
_journal_paper_doi               10.1021/ol500877c
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C23 H18 O2'
_chemical_formula_sum            'C23 H18 O2'
_chemical_formula_weight         326.37
_chemical_melting_point_gt       376
_chemical_melting_point_lt       377
_chemical_name_systematic
; 
 3--Benzoyl--2,4--diphenyl--4,5--dihydrofuran
 
;
_space_group_IT_number           2
_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           SHELXL97
_cell_angle_alpha                63.28(2)
_cell_angle_beta                 80.45(2)
_cell_angle_gamma                70.81(2)
_cell_formula_units_Z            2
_cell_length_a                   9.661(3)
_cell_length_b                   9.9907(14)
_cell_length_c                   10.7602(15)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      39.74
_cell_measurement_theta_min      35.30
_cell_volume                     875.9(4)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4        (Harms & Wocadlo, 1995)'
_computing_structure_refinement  'SHELXL97     (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97     (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device       '\k--geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non--profiled \w--scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine--focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0143
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3471
_diffrn_reflns_theta_full        74.94
_diffrn_reflns_theta_max         74.94
_diffrn_reflns_theta_min         4.60
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    0.614
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             344
_exptl_crystal_preparation       'Pethroleum ether - ethyl acetate'
_exptl_crystal_size_max          .2
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .2
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3471
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0476
_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^)+(0.0775P)^2^+0.1140P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1275
_refine_ls_wR_factor_ref         0.1304
_reflns_number_gt                3154
_reflns_number_total             3471
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            ol500877c_si_001.cif
_cod_data_source_block           chk1228
_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.

'_diffrn_radiation_probe' value 'x--ray' changed to
'x-ray' 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.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1516047--1516048.cif.
;
_cod_database_code               1516047
_diffrn_standards_decay_corr_max 1.010
_diffrn_standards_decay_corr_min 0.982