Chiral organic contact ion pairs in metal-free catalytic enantioselective oxidative cross-dehydrogenative coupling of tertiary amines to ketones
Zhang, Gen; Ma, Yunxia; Wang, Shoulei; Kong, Weidong; Wang, Rui; Chemical Science 4 (2013) 2645–; doi:10.1039/c3sc50604e

data_1514674
_publ_section_title
;
 Chiral organic contact ion pairs in metal-free catalytic enantioselective
 oxidative cross-dehydrogenative coupling of tertiary amines to ketones
;
_journal_issue                   6
_journal_name_full               'Chemical Science'
_journal_page_first              2645
_journal_paper_doi               10.1039/c3sc50604e
_journal_volume                  4
_journal_year                    2013
_chemical_formula_moiety         'C20 H20 F N O S'
_chemical_formula_sum            'C20 H20 F N O S'
_chemical_formula_weight         341.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-11-16
_audit_creation_method
;
Olex2 1.2
(compiled Nov 5 2012 18:22:26, GUI svn.r4372)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.806(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.7008(2)
_cell_length_b                   14.8959(6)
_cell_length_c                   16.9986(6)
_cell_measurement_reflns_used    2030
_cell_measurement_temperature    292.05(10)
_cell_measurement_theta_max      28.5363
_cell_measurement_theta_min      2.9811
_cell_volume                     1692.96(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      292.05(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.9806
_diffrn_measurement_details
;
1 omega -92.00 -61.00 1.0000 25.0000
omega____ theta____ kappa____ phi______ frames
- -19.3492 -38.0000 -30.0000 31
2 omega 43.00 100.00 1.0000 25.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 -178.0000 -30.0000 57
3 omega 21.00 83.00 1.0000 25.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 57.0000 150.0000 62
4 omega 0.00 87.00 1.0000 25.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 57.0000 60.0000 87
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0607504000
_diffrn_orient_matrix_UB_12      0.0313059000
_diffrn_orient_matrix_UB_13      0.0188153000
_diffrn_orient_matrix_UB_21      0.0290470000
_diffrn_orient_matrix_UB_22      -0.0194846000
_diffrn_orient_matrix_UB_23      0.0370814000
_diffrn_orient_matrix_UB_31      0.0819797000
_diffrn_orient_matrix_UB_32      0.0301351000
_diffrn_orient_matrix_UB_33      0.0044078000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7271
_diffrn_reflns_theta_full        28.60
_diffrn_reflns_theta_max         28.60
_diffrn_reflns_theta_min         2.99
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3798
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0540
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1522
_refine_ls_wR_factor_ref         0.1823
_reflns_number_gt                2638
_reflns_number_total             3798
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3sc50604e.txt
_cod_data_source_block           exp_444
_cod_original_cell_volume        1692.96(11)
_cod_database_code               1514674
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
H1 of C1, H4 of C4, H3 of C3, H5 of C5, H6 of C6, {H8A,H8B} of C8, {H9A,
H9B} of C9, H12 of C12, H13 of C13, H14 of C14, H15 of C15, H16 of C16, {H19A,
H19B} of C19, {H20A,H20B} of C20, {H21A,H21B} of C21
2.a Ternary CH refined with riding coordinates:
C1(H1), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
C8(H8A,H8B), C9(H9A,H9B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15)
;