#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:55:00 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180202 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/96/7109633.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7109633
loop_
_publ_author_name
'Yingle Liu'
'Jiawang Liu'
'Yangen Huang'
'Feng-Ling Qing'
_publ_section_title
;
 Lewis acid-catalyzed regioselective synthesis of chiral alpha-fluoroalkyl
 amines via asymmetric addition of silyl dienolates to fluorinated
 sulfinylimines
;
_journal_name_full               Chem.Commun.
_journal_page_first              7492
_journal_paper_doi               10.1039/c3cc43741h
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H23 F3 N O3 S'
_chemical_formula_weight         342.39
_chemical_name_systematic
;
?
;
_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                 113.544(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.4050(12)
_cell_length_b                   9.9217(12)
_cell_length_c                   10.9244(14)
_cell_measurement_reflns_used    2832
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      52.259
_cell_measurement_theta_min      4.849
_cell_volume                     934.5(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5687
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24669
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             362
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.147
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3668
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0752P)^2^+0.0463P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1153
_reflns_number_gt                3369
_reflns_number_total             3668
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc43741h.txt
_cod_data_source_block           cd212628
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7109633
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.67325(6) 0.13385(6) 0.61019(5) 0.05040(16) Uani 1 1 d . . .
F1 F 0.3365(3) 0.0903(2) 0.6228(3) 0.1174(9) Uani 1 1 d . B .
F2 F 0.2493(2) 0.2887(2) 0.5982(3) 0.1151(9) Uani 1 1 d . B .
F3 F 0.3050(3) 0.1870(3) 0.7810(3) 0.1345(10) Uani 1 1 d . B .
N1 N 0.5696(2) 0.26329(19) 0.6263(2) 0.0482(4) Uani 1 1 d D . .
O1 O 0.5765(2) 0.02834(19) 0.5178(2) 0.0678(5) Uani 1 1 d . . .
O2 O 0.8017(2) 0.3777(2) 0.9130(2) 0.0818(6) Uani 1 1 d . . .
O3 O 0.70632(19) 0.57658(18) 0.81800(18) 0.0604(4) Uani 1 1 d . . .
C1 C 0.5157(3) 0.2618(2) 0.7323(2) 0.0508(5) Uani 1 1 d . B .
H1 H 0.5831 0.2017 0.8028 0.061 Uiso 1 1 calc R . .
C2 C 0.5272(3) 0.4039(2) 0.7910(2) 0.0509(5) Uani 1 1 d D . .
H2 H 0.4632 0.4669 0.7218 0.061 Uiso 1 1 calc R A 1
C3 C 0.4874(14) 0.4141(19) 0.9149(10) 0.070(2) Uani 0.60 1 d PDU B 1
H3 H 0.5376 0.3583 0.9880 0.084 Uiso 0.60 1 calc PR B 1
C4 C 0.3825(7) 0.5018(6) 0.9180(6) 0.0915(13) Uani 0.75 1 d PDU B 1
H4A H 0.3321 0.5577 0.8451 0.110 Uiso 0.75 1 calc PR B 1
H4B H 0.3593 0.5073 0.9930 0.110 Uiso 0.75 1 calc PR B 1
C3' C 0.458(3) 0.415(3) 0.8893(17) 0.076(3) Uani 0.40 1 d PDU B 2
H3' H 0.3580 0.3801 0.8552 0.091 Uiso 0.40 1 calc PR B 2
C4' C 0.496(3) 0.457(2) 1.0079(18) 0.107(3) Uani 0.25 1 d PDU B 2
H4'1 H 0.5936 0.4946 1.0542 0.128 Uiso 0.25 1 calc PR B 2
H4'2 H 0.4259 0.4514 1.0483 0.128 Uiso 0.25 1 calc PR B 2
C5 C 0.3506(4) 0.2076(3) 0.6822(3) 0.0704(8) Uani 1 1 d . . .
C6 C 0.6973(3) 0.4492(3) 0.8479(2) 0.0515(5) Uani 1 1 d . B .
C7 C 0.8505(3) 0.6579(3) 0.8822(3) 0.0661(7) Uani 1 1 d . . .
C8 C 0.8954(5) 0.6594(5) 1.0292(3) 0.1052(14) Uani 1 1 d . . .
H8A H 0.8110 0.6941 1.0481 0.158 Uiso 1 1 calc R . .
H8B H 0.9849 0.7157 1.0708 0.158 Uiso 1 1 calc R . .
H8C H 0.9191 0.5694 1.0636 0.158 Uiso 1 1 calc R . .
C9 C 0.7997(5) 0.7952(4) 0.8235(6) 0.1274(19) Uani 1 1 d . . .
H9A H 0.7852 0.7950 0.7314 0.191 Uiso 1 1 calc R . .
H9B H 0.8775 0.8603 0.8716 0.191 Uiso 1 1 calc R . .
H9C H 0.7038 0.8182 0.8300 0.191 Uiso 1 1 calc R . .
C10 C 0.9763(4) 0.6041(4) 0.8450(5) 0.1006(13) Uani 1 1 d . . .
H10A H 1.0002 0.5132 0.8767 0.151 Uiso 1 1 calc R . .
H10B H 1.0673 0.6591 0.8847 0.151 Uiso 1 1 calc R . .
H10C H 0.9423 0.6054 0.7496 0.151 Uiso 1 1 calc R . .
C11 C 0.7708(3) 0.2218(2) 0.5157(3) 0.0551(6) Uani 1 1 d . . .
C12 C 0.6509(4) 0.2680(3) 0.3813(3) 0.0668(7) Uani 1 1 d . . .
H12A H 0.5894 0.3391 0.3947 0.100 Uiso 1 1 calc R . .
H12B H 0.5849 0.1936 0.3373 0.100 Uiso 1 1 calc R . .
H12C H 0.7026 0.3003 0.3270 0.100 Uiso 1 1 calc R . .
C13 C 0.8642(3) 0.3386(3) 0.6003(3) 0.0692(7) Uani 1 1 d . . .
H13A H 0.9327 0.3732 0.5622 0.104 Uiso 1 1 calc R . .
H13B H 0.9239 0.3075 0.6894 0.104 Uiso 1 1 calc R . .
H13C H 0.7948 0.4085 0.6027 0.104 Uiso 1 1 calc R . .
C14 C 0.8781(3) 0.1134(3) 0.4990(4) 0.0787(8) Uani 1 1 d . . .
H14A H 0.8169 0.0404 0.4466 0.118 Uiso 1 1 calc R . .
H14B H 0.9460 0.0805 0.5853 0.118 Uiso 1 1 calc R . .
H14C H 0.9387 0.1517 0.4548 0.118 Uiso 1 1 calc R . .
H1A H 0.519(2) 0.308(2) 0.5577(18) 0.031(5) Uiso 1 1 d D . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0517(3) 0.0349(2) 0.0650(3) 0.0001(2) 0.0238(2) 0.0030(2)
F1 0.0954(14) 0.0661(12) 0.212(3) -0.0555(14) 0.0839(17) -0.0362(10)
F2 0.0494(9) 0.0795(13) 0.190(2) 0.0088(14) 0.0203(12) -0.0123(9)
F3 0.1377(18) 0.148(2) 0.165(2) -0.0275(18) 0.1103(18) -0.0684(18)
N1 0.0513(10) 0.0362(9) 0.0584(11) 0.0039(8) 0.0233(8) 0.0047(7)
O1 0.0775(12) 0.0429(9) 0.0921(13) -0.0149(9) 0.0436(10) -0.0135(8)
O2 0.0540(10) 0.0684(13) 0.1019(15) 0.0093(11) 0.0090(10) 0.0063(10)
O3 0.0482(9) 0.0486(9) 0.0742(10) -0.0032(8) 0.0138(8) -0.0058(7)
C1 0.0535(12) 0.0380(11) 0.0646(13) 0.0064(10) 0.0274(10) -0.0009(9)
C2 0.0456(11) 0.0451(12) 0.0646(13) -0.0022(10) 0.0247(10) -0.0002(9)
C3 0.076(5) 0.077(3) 0.068(4) -0.015(4) 0.038(4) -0.008(4)
C4 0.101(3) 0.098(3) 0.102(3) -0.012(3) 0.069(3) 0.010(3)
C3' 0.075(6) 0.081(4) 0.079(5) -0.012(5) 0.039(5) -0.014(5)
C4' 0.113(7) 0.100(6) 0.106(6) -0.008(6) 0.042(6) -0.022(6)
C5 0.0701(16) 0.0474(15) 0.112(2) -0.0108(15) 0.0552(17) -0.0139(13)
C6 0.0450(11) 0.0511(13) 0.0568(12) -0.0043(10) 0.0184(10) -0.0002(10)
C7 0.0528(12) 0.062(2) 0.0763(15) -0.0161(13) 0.0186(11) -0.0153(11)
C8 0.103(2) 0.126(4) 0.085(2) -0.045(2) 0.0356(19) -0.050(3)
C9 0.096(3) 0.065(2) 0.182(5) 0.004(3) 0.014(3) -0.030(2)
C10 0.080(2) 0.102(3) 0.137(3) -0.044(2) 0.062(2) -0.035(2)
C11 0.0510(12) 0.0447(12) 0.0752(15) -0.0104(11) 0.0312(11) -0.0059(10)
C12 0.0801(17) 0.0590(15) 0.0685(15) -0.0046(12) 0.0373(13) -0.0101(13)
C13 0.0630(14) 0.0602(16) 0.0888(19) -0.0166(14) 0.0348(13) -0.0207(13)
C14 0.0701(16) 0.066(2) 0.116(2) -0.0118(17) 0.0543(16) 0.0050(15)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 S1 N1 112.94(10)
O1 S1 C11 104.99(11)
N1 S1 C11 97.90(10)
C1 N1 S1 119.17(16)
C1 N1 H1A 118.1(14)
S1 N1 H1A 117.5(15)
C6 O3 C7 122.7(2)
N1 C1 C5 110.5(2)
N1 C1 C2 109.75(18)
C5 C1 C2 111.5(2)
N1 C1 H1 108.3
C5 C1 H1 108.3
C2 C1 H1 108.3
C3' C2 C6 112.2(10)
C3' C2 C1 113.3(13)
C6 C2 C1 109.06(19)
C3' C2 C3 11.2(12)
C6 C2 C3 101.8(5)
C1 C2 C3 115.1(8)
C3' C2 H2 101.8
C6 C2 H2 110.2
C1 C2 H2 110.2
C3 C2 H2 110.2
C4 C3 C2 120.5(10)
C4 C3 H3 119.7
C2 C3 H3 119.7
C3 C4 H4A 120.0
C3 C4 H4B 120.0
H4A C4 H4B 120.0
C4' C3' C2 138(2)
C4' C3' H3' 110.8
C2 C3' H3' 110.9
C3' C4' H4'1 120.0
C3' C4' H4'2 120.0
H4'1 C4' H4'2 120.0
F2 C5 F1 107.4(3)
F2 C5 F3 106.6(3)
F1 C5 F3 105.3(3)
F2 C5 C1 112.8(2)
F1 C5 C1 112.2(2)
F3 C5 C1 112.1(3)
O2 C6 O3 126.9(2)
O2 C6 C2 123.1(2)
O3 C6 C2 109.9(2)
C8 C7 O3 109.0(2)
C8 C7 C10 112.5(3)
O3 C7 C10 110.4(2)
C8 C7 C9 110.9(4)
O3 C7 C9 102.4(2)
C10 C7 C9 111.1(4)
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C7 C9 H9A 109.5
C7 C9 H9B 109.5
H9A C9 H9B 109.5
C7 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C7 C10 H10A 109.5
C7 C10 H10B 109.5
H10A C10 H10B 109.5
C7 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C12 C11 C13 112.5(2)
C12 C11 C14 111.5(2)
C13 C11 C14 111.0(2)
C12 C11 S1 109.80(17)
C13 C11 S1 108.31(18)
C14 C11 S1 103.41(19)
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C11 C13 H13A 109.5
C11 C13 H13B 109.5
H13A C13 H13B 109.5
C11 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C11 C14 H14A 109.5
C11 C14 H14B 109.5
H14A C14 H14B 109.5
C11 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4864(19)
S1 N1 1.6640(19)
S1 C11 1.851(3)
F1 C5 1.312(3)
F2 C5 1.304(4)
F3 C5 1.328(4)
N1 C1 1.437(3)
N1 H1A 0.837(16)
O2 C6 1.190(3)
O3 C6 1.317(3)
O3 C7 1.491(3)
C1 C5 1.523(4)
C1 C2 1.535(3)
C1 H1 0.9800
C2 C3' 1.463(16)
C2 C6 1.534(3)
C2 C3 1.545(10)
C2 H2 0.9800
C3 C4 1.326(13)
C3 H3 0.9300
C4 H4A 0.9300
C4 H4B 0.9300
C3' C4' 1.272(17)
C3' H3' 0.9300
C4' H4'1 0.9300
C4' H4'2 0.9300
C7 C8 1.489(4)
C7 C10 1.495(4)
C7 C9 1.501(5)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 C12 1.521(4)
C11 C13 1.523(3)
C11 C14 1.534(4)
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.837(16) 2.382(19) 3.091(3) 142.9(19) 2_656
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 S1 N1 C1 92.32(19)
C11 S1 N1 C1 -157.68(18)
S1 N1 C1 C5 -95.3(2)
S1 N1 C1 C2 141.38(17)
N1 C1 C2 C3' 173.5(9)
C5 C1 C2 C3' 50.7(10)
N1 C1 C2 C6 -60.9(3)
C5 C1 C2 C6 176.3(2)
N1 C1 C2 C3 -174.5(5)
C5 C1 C2 C3 62.7(6)
C3' C2 C3 C4 -44(9)
C6 C2 C3 C4 115.3(12)
C1 C2 C3 C4 -126.9(12)
C6 C2 C3' C4' 5(4)
C1 C2 C3' C4' 129(4)
C3 C2 C3' C4' 27(7)
N1 C1 C5 F2 -68.5(3)
C2 C1 C5 F2 53.9(3)
N1 C1 C5 F1 52.9(3)
C2 C1 C5 F1 175.3(3)
N1 C1 C5 F3 171.2(2)
C2 C1 C5 F3 -66.5(3)
C7 O3 C6 O2 -10.6(4)
C7 O3 C6 C2 166.9(2)
C3' C2 C6 O2 82.6(13)
C1 C2 C6 O2 -43.7(3)
C3 C2 C6 O2 78.4(8)
C3' C2 C6 O3 -95.0(13)
C1 C2 C6 O3 138.7(2)
C3 C2 C6 O3 -99.2(7)
C6 O3 C7 C8 -58.6(4)
C6 O3 C7 C10 65.5(4)
C6 O3 C7 C9 -176.1(3)
O1 S1 C11 C12 52.9(2)
N1 S1 C11 C12 -63.44(19)
O1 S1 C11 C13 176.09(19)
N1 S1 C11 C13 59.71(19)
O1 S1 C11 C14 -66.1(2)
N1 S1 C11 C14 177.51(19)