#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:30:10 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178471 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/92/4029295.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_4029295
loop_
_publ_author_name
'Kondo, Yasuhiro'
'Sasaki, Michiko'
'Kawahata, Masatoshi'
'Yamaguchi, Kentaro'
'Takeda, Kei'
_publ_section_title
;
 Enantioselective Synthesis of α-Silylamines by
 Meerwein-Ponndorf-Verley-Type Reduction of α-Silylimines by a Chiral
 Lithium Amide.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3601
_journal_page_last               3609
_journal_paper_doi               10.1021/jo500441a
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H23 N O2 S Si'
_chemical_formula_weight         333.51
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 115.62(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.545(5)
_cell_length_b                   9.535(4)
_cell_length_c                   10.077(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    173
_cell_measurement_theta_max      29.5
_cell_measurement_theta_min      25.1
_cell_volume                     913.6(7)
_computing_cell_refinement       WinAFC
_computing_data_collection       WinAFC
_computing_data_reduction        CrystalStructure
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  Yadokari-XG
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3621
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.916
_diffrn_reflns_theta_min         4.650
_exptl_absorpt_coefficient_mu    2.247
_exptl_absorpt_correction_T_max  0.889
_exptl_absorpt_correction_T_min  0.809
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_description       plate
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3220
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0956P)²+0.1394P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1269
_reflns_Friedel_coverage         0.823
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.937
_reflns_number_gt                3066
_reflns_number_total             3220
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo500441a_si_002.cif
_cod_data_source_block           YSK-XI-2134C
_cod_depositor_comments
;Adding full bibliography for
 ./tmp-cod-update-bibliographies-12971/cifs/4029295.cif.
;
_cod_original_cell_volume        913.7(7)
_cod_database_code               4029295
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2013-2
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.1174(4) 0.2959(4) 0.7054(4) 0.0291(8) Uani 1 1 d . .
H1 H 0.0888 0.3931 0.6761 0.035 Uiso 1 1 calc R U
C2 C 0.2753(4) 0.2904(4) 0.7615(4) 0.0330(9) Uani 1 1 d . .
C3 C 0.3468(4) 0.1690(5) 0.7611(5) 0.0410(9) Uani 1 1 d . .
H2 H 0.2967 0.0884 0.7170 0.049 Uiso 1 1 calc R U
C4 C 0.4936(5) 0.1663(7) 0.8262(6) 0.0620(15) Uani 1 1 d . .
H3 H 0.5410 0.0848 0.8241 0.074 Uiso 1 1 calc R U
C5 C 0.5679(5) 0.2854(10) 0.8939(7) 0.075(2) Uani 1 1 d . .
H4 H 0.6656 0.2830 0.9412 0.090 Uiso 1 1 calc R U
C6 C 0.4972(6) 0.4082(9) 0.8915(8) 0.074(2) Uani 1 1 d . .
H5 H 0.5475 0.4890 0.9346 0.089 Uiso 1 1 calc R U
C7 C 0.3524(5) 0.4110(6) 0.8253(6) 0.0486(11) Uani 1 1 d . .
H6 H 0.3056 0.4942 0.8231 0.058 Uiso 1 1 calc R U
C8 C 0.1343(5) 0.0765(5) 0.9364(5) 0.0446(10) Uani 1 1 d . .
H7 H 0.2347 0.0755 0.9724 0.067 Uiso 1 1 calc R U
H8 H 0.0937 0.0073 0.8604 0.067 Uiso 1 1 calc R U
H9 H 0.1098 0.0556 1.0156 0.067 Uiso 1 1 calc R U
C9 C 0.1461(5) 0.3897(5) 1.0031(5) 0.0460(10) Uani 1 1 d . .
H10 H 0.1143 0.3781 1.0785 0.069 Uiso 1 1 calc R U
H11 H 0.1190 0.4807 0.9591 0.069 Uiso 1 1 calc R U
H12 H 0.2467 0.3812 1.0456 0.069 Uiso 1 1 calc R U
C10 C -0.1301(4) 0.2547(6) 0.7850(5) 0.0493(10) Uani 1 1 d . .
H13 H -0.1575 0.2255 0.8599 0.074 Uiso 1 1 calc R U
H14 H -0.1693 0.1918 0.7027 0.074 Uiso 1 1 calc R U
H15 H -0.1641 0.3480 0.7534 0.074 Uiso 1 1 calc R U
C11 C 0.1604(4) 0.2692(5) 0.3935(4) 0.0386(8) Uani 1 1 d . .
C12 C 0.2384(5) 0.3922(5) 0.4255(5) 0.0440(10) Uani 1 1 d . .
H16 H 0.2064 0.4725 0.4538 0.053 Uiso 1 1 calc R U
C13 C 0.3652(5) 0.3930(6) 0.4142(5) 0.0539(13) Uani 1 1 d . .
H17 H 0.4174 0.4754 0.4347 0.065 Uiso 1 1 calc R U
C14 C 0.4160(5) 0.2751(7) 0.3736(5) 0.0517(11) Uani 1 1 d . .
C15 C 0.3358(6) 0.1525(6) 0.3425(6) 0.0524(12) Uani 1 1 d . .
H18 H 0.3678 0.0720 0.3146 0.063 Uiso 1 1 calc R U
C16 C 0.2092(5) 0.1494(5) 0.3528(5) 0.0451(10) Uani 1 1 d . .
H19 H 0.1570 0.0670 0.3324 0.054 Uiso 1 1 calc R U
C17 C 0.5528(6) 0.2783(9) 0.3583(8) 0.0746(18) Uani 1 1 d . .
H20 H 0.5840 0.1841 0.3563 0.112 Uiso 1 1 calc R U
H21 H 0.6228 0.3276 0.4404 0.112 Uiso 1 1 calc R U
H22 H 0.5383 0.3253 0.2686 0.112 Uiso 1 1 calc R U
N1 N 0.0357(3) 0.2069(3) 0.5763(4) 0.0311(7) Uani 1 1 d . .
H23 H 0.050(5) 0.123(7) 0.588(6) 0.049(15) Uiso 1 1 d . .
S1 S 0.00179(9) 0.26114(9) 0.41215(9) 0.0349(3) Uani 1 1 d . .
Si1 Si 0.06566(9) 0.25273(12) 0.86042(10) 0.0301(3) Uani 1 1 d . .
O1 O -0.0848(3) 0.1548(3) 0.3128(3) 0.0455(8) Uani 1 1 d . .
O2 O -0.0513(3) 0.4016(3) 0.4000(3) 0.0453(7) Uani 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 '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
N1 C1 C2 115.9(3)
N1 C1 Si1 109.4(2)
C2 C1 Si1 110.2(3)
N1 C1 H1 106.9
C2 C1 H1 106.9
Si1 C1 H1 106.9
C3 C2 C7 118.8(4)
C3 C2 C1 122.9(4)
C7 C2 C1 118.2(4)
C2 C3 C4 120.6(5)
C2 C3 H2 119.7
C4 C3 H2 119.7
C5 C4 C3 119.6(5)
C5 C4 H3 120.2
C3 C4 H3 120.2
C4 C5 C6 120.1(4)
C4 C5 H4 120.0
C6 C5 H4 120.0
C7 C6 C5 120.1(6)
C7 C6 H5 119.9
C5 C6 H5 119.9
C6 C7 C2 120.7(5)
C6 C7 H6 119.6
C2 C7 H6 119.6
Si1 C8 H7 109.5
Si1 C8 H8 109.5
H7 C8 H8 109.5
Si1 C8 H9 109.5
H7 C8 H9 109.5
H8 C8 H9 109.5
Si1 C9 H10 109.5
Si1 C9 H11 109.5
H10 C9 H11 109.5
Si1 C9 H12 109.5
H10 C9 H12 109.5
H11 C9 H12 109.5
Si1 C10 H13 109.5
Si1 C10 H14 109.5
H13 C10 H14 109.5
Si1 C10 H15 109.5
H13 C10 H15 109.5
H14 C10 H15 109.5
C16 C11 C12 120.5(4)
C16 C11 S1 119.1(4)
C12 C11 S1 120.4(4)
C11 C12 C13 118.7(5)
C11 C12 H16 120.7
C13 C12 H16 120.7
C14 C13 C12 122.0(5)
C14 C13 H17 119.0
C12 C13 H17 119.0
C13 C14 C15 118.2(4)
C13 C14 C17 121.5(5)
C15 C14 C17 120.3(5)
C16 C15 C14 120.8(5)
C16 C15 H18 119.6
C14 C15 H18 119.6
C15 C16 C11 119.9(5)
C15 C16 H19 120.1
C11 C16 H19 120.1
C14 C17 H20 109.5
C14 C17 H21 109.5
H20 C17 H21 109.5
C14 C17 H22 109.5
H20 C17 H22 109.5
H21 C17 H22 109.5
C1 N1 S1 120.2(3)
C1 N1 H23 116(4)
S1 N1 H23 114(4)
O2 S1 O1 119.39(19)
O2 S1 N1 106.90(19)
O1 S1 N1 106.22(19)
O2 S1 C11 107.6(2)
O1 S1 C11 107.6(2)
N1 S1 C11 108.79(18)
C9 Si1 C8 110.6(2)
C9 Si1 C10 111.3(2)
C8 Si1 C10 110.0(2)
C9 Si1 C1 106.62(19)
C8 Si1 C1 109.51(18)
C10 Si1 C1 108.74(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.478(5)
C1 C2 1.510(5)
C1 Si1 1.909(4)
C1 H1 0.9800
C2 C3 1.382(6)
C2 C7 1.395(6)
C3 C4 1.396(6)
C3 H2 0.9300
C4 C5 1.381(10)
C4 H3 0.9300
C5 C6 1.382(11)
C5 H4 0.9300
C6 C7 1.377(7)
C6 H5 0.9300
C7 H6 0.9300
C8 Si1 1.859(5)
C8 H7 0.9600
C8 H8 0.9600
C8 H9 0.9600
C9 Si1 1.854(5)
C9 H10 0.9600
C9 H11 0.9600
C9 H12 0.9600
C10 Si1 1.866(4)
C10 H13 0.9600
C10 H14 0.9600
C10 H15 0.9600
C11 C16 1.386(7)
C11 C12 1.388(6)
C11 S1 1.764(4)
C12 C13 1.390(7)
C12 H16 0.9300
C13 C14 1.381(8)
C13 H17 0.9300
C14 C15 1.397(8)
C14 C17 1.515(7)
C15 C16 1.383(7)
C15 H18 0.9300
C16 H19 0.9300
C17 H20 0.9600
C17 H21 0.9600
C17 H22 0.9600
N1 S1 1.619(4)
N1 H23 0.81(6)
S1 O2 1.436(3)
S1 O1 1.440(3)
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
N1 C1 C2 C3 -36.2(5)
Si1 C1 C2 C3 88.8(4)
N1 C1 C2 C7 148.3(4)
Si1 C1 C2 C7 -86.8(4)
C7 C2 C3 C4 1.4(6)
C1 C2 C3 C4 -174.2(4)
C2 C3 C4 C5 1.1(8)
C3 C4 C5 C6 -2.8(10)
C4 C5 C6 C7 1.9(10)
C5 C6 C7 C2 0.7(9)
C3 C2 C7 C6 -2.3(7)
C1 C2 C7 C6 173.5(5)
C16 C11 C12 C13 0.7(6)
S1 C11 C12 C13 177.8(3)
C11 C12 C13 C14 -0.6(7)
C12 C13 C14 C15 0.3(7)
C12 C13 C14 C17 178.6(5)
C13 C14 C15 C16 -0.2(7)
C17 C14 C15 C16 -178.5(5)
C14 C15 C16 C11 0.4(7)
C12 C11 C16 C15 -0.6(7)
S1 C11 C16 C15 -177.8(4)
C2 C1 N1 S1 -82.2(4)
Si1 C1 N1 S1 152.5(2)
C1 N1 S1 O2 -48.4(3)
C1 N1 S1 O1 -176.9(3)
C1 N1 S1 C11 67.6(3)
C16 C11 S1 O2 -158.9(3)
C12 C11 S1 O2 23.9(4)
C16 C11 S1 O1 -29.1(4)
C12 C11 S1 O1 153.8(3)
C16 C11 S1 N1 85.6(4)
C12 C11 S1 N1 -91.6(4)
