Intermolecular Reductive Coupling of Esters with Benzophenones by Low-valent Titanium: Synthesis of Diarylmethyl ketones Revisited.
Kise, Naoki; Sakurai, Toshihiko; The Journal of organic chemistry  (2015) 150317073852008–; doi:10.1021/acs.joc.5b00102

data_4030818
_publ_section_title
;
 Intermolecular Reductive Coupling of Esters with Benzophenones by
 Low-valent Titanium: Synthesis of Diarylmethyl ketones Revisited.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              150317073852008
_journal_paper_doi               10.1021/acs.joc.5b00102
_journal_year                    2015
_chemical_formula_moiety         'C19 H19 N O2'
_chemical_formula_sum            'C19 H19 N O2'
_chemical_formula_weight         293.35
_chemical_melting_point          485.5(5)
_chemical_name_systematic
; 
(1R*,7aS*)-1-benzhydryl-tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one 
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.933(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.402(3)
_cell_length_b                   15.737(3)
_cell_length_c                   10.672(3)
_cell_measurement_temperature    298(2)
_cell_volume                     1555.4(7)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_publication_material  yadokari-XG
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0185
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6741
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.23
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.9761
_exptl_absorpt_correction_T_min  0.9606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3005
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0617
_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^)+(0.1068P)^2^+0.4597P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1601
_refine_ls_wR_factor_ref         0.1763
_reflns_number_gt                2590
_reflns_number_total             3005
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b00102_si_005.cif
_cod_data_source_block           rac-11a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '485-486' was changed to '485.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 3105 2015-03-04 15:46:00Z robertas 
;
_cod_original_cell_volume        1555.5(7)
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               4030818