Isothiourea-mediated asymmetric Michael-lactonisation of trifluoromethylenones: a synthetic and mechanistic study
Morrill, Louis C.; Douglas, James; Lebl, Tomas; Slawin, Alexandra M. Z.; Fox, David J.; Smith, Andrew D.; Chemical Science 4 (2013) 4146–; doi:10.1039/c3sc51791h

data_1514744
_publ_section_title
;
 Isothiourea-mediated asymmetric Michael-lactonisation of
 trifluoromethylenones: a synthetic and mechanistic study
;
_journal_issue                   11
_journal_name_full               'Chemical Science'
_journal_page_first              4146
_journal_paper_doi               10.1039/c3sc51791h
_journal_volume                  4
_journal_year                    2013
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C22 H19 F3 O2'
_chemical_formula_sum            'C22 H19 F3 O2'
_chemical_formula_weight         372.37
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 104.404(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.039(5)
_cell_length_b                   27.449(18)
_cell_length_c                   11.299(8)
_cell_measurement_reflns_used    1776
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      67.5
_cell_measurement_theta_min      21.2
_cell_volume                     1814(2)
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_collection       'CrystalClear (Rigaku Corp., 2004)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2004)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1915
_diffrn_reflns_av_sigmaI/netI    0.1200
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24420
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         67.80
_diffrn_reflns_theta_min         3.22
_exptl_absorpt_coefficient_mu    0.902
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       0.0087(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         6439
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.1492
_refine_ls_R_factor_gt           0.1131
_refine_ls_shift/su_max          0.053
_refine_ls_shift/su_mean         0.014
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1709P)^2^+0.2700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2972
_refine_ls_wR_factor_ref         0.3357
_reflns_number_gt                3884
_reflns_number_total             6439
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3sc51791h.txt
_cod_data_source_block           41
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1514744