N-Heterocyclic carbene (NHC) catalyzed chemoselective acylation of alcohols in the presence of amines with various acylating reagents
Samanta, Ramesh C.; De Sarkar, Suman; Fröhlich, Roland; Grimme, Stefan; Studer, Armido; Chemical Science 4 (2013) 2177–; doi:10.1039/c3sc00099k

data_1514717
_publ_section_title
;
 N-Heterocyclic carbene (NHC) catalyzed chemoselective acylation of
 alcohols in the presence of amines with various acylating reagents
;
_journal_issue                   5
_journal_name_full               'Chemical Science'
_journal_page_first              2177
_journal_paper_doi               10.1039/c3sc00099k
_journal_volume                  4
_journal_year                    2013
_chemical_formula_sum            'C15 H17 F3 N2 O4 S'
_chemical_formula_weight         378.37
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 92.806(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6013(1)
_cell_length_b                   7.0186(1)
_cell_length_c                   25.4572(4)
_cell_measurement_reflns_used    2871
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      0.88
_cell_volume                     1713.44(4)
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            11633
_diffrn_reflns_theta_full        66.45
_diffrn_reflns_theta_max         66.45
_diffrn_reflns_theta_min         4.61
_exptl_absorpt_coefficient_mu    2.191
_exptl_absorpt_correction_T_max  0.8617
_exptl_absorpt_correction_T_min  0.5317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2930
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0502
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0718P)^2^+1.0085P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1395
_reflns_number_gt                2588
_reflns_number_total             2930
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3sc00099k.txt
_cod_data_source_block           stu6327
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1514717