#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/16/7151613.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_7151613
loop_
_publ_author_name
'Charrier, Jean-Damien'
'Hitchcock, Peter B.'
'Young, Douglas W.'
_publ_section_title
;
 Synthesis of (2S,3R)-[3',3',3'-2H3]-valine and (2S,3S)-4-fluorovaline.
;
_journal_issue                   9
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1310
_journal_page_last               1314
_journal_paper_doi               10.1039/b401646g
_journal_volume                  2
_journal_year                    2004
_chemical_absolute_configuration syn
_chemical_formula_sum            'C27 H34 D3 N O4 Si'
_chemical_formula_weight         470.7
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 105.26(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.767(5)
_cell_length_b                   13.052(4)
_cell_length_c                   11.178(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      12
_cell_volume                     1374.7(10)
_computing_cell_refinement       'Enraf-Nonius CAD4'
_computing_data_collection       'Enraf-Nonius CAD4'
_computing_publication_material  SHELXL-93
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       ' Enraf-Nonius CAD4'
_diffrn_measurement_method       ω--2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2272
_diffrn_reflns_theta_max         59.99
_diffrn_reflns_theta_min         4.10
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.991
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.08(5)
_refine_ls_extinction_coef       0.0124(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.047
_refine_ls_goodness_of_fit_obs   1.058
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         2145
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_restrained_S_obs      1.058
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_obs          0.0479
_refine_ls_shift/esd_max         -0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0745P)²+0.0261P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1277
_refine_ls_wR_factor_obs         0.1173
_reflns_number_observed          1819
_reflns_number_total             2145
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b401646g.txt
_cod_data_source_block           apr1098
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0745P)^2^+0.0261P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0745P)^2^+0.0261P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7151613
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Si Si 0.45246(11) 0.35390(9) 0.09334(10) 0.0425(3) Uani 1 d . .
O1 O 0.4488(3) 0.3952(2) 0.2313(3) 0.0486(8) Uani 1 d . .
O2 O 0.1923(5) 0.3640(4) 0.4658(5) 0.103(2) Uani 1 d . .
O3 O 0.3147(4) 0.6531(3) 0.3724(4) 0.0745(11) Uani 1 d . .
O4 O 0.1366(3) 0.5603(3) 0.4101(4) 0.0633(9) Uani 1 d . .
N N 0.3483(4) 0.4863(3) 0.4274(4) 0.0514(10) Uani 1 d . .
C1 C 0.4965(5) 0.4897(4) 0.4201(4) 0.0505(12) Uani 1 d . .
H1 H 0.5417 0.5518 0.4616 0.061 Uiso 1 calc R .
C2 C 0.5627(6) 0.3957(5) 0.4966(5) 0.065(2) Uani 1 d . .
H2 H 0.6291 0.3627 0.4565 0.078 Uiso 1 calc R .
C3 C 0.4388(7) 0.3238(5) 0.4917(6) 0.079(2) Uani 1 d . .
H3A H 0.4327 0.2720 0.4282 0.095 Uiso 1 calc R .
H3B H 0.4500 0.2899 0.5709 0.095 Uiso 1 calc R .
C4 C 0.3088(6) 0.3896(4) 0.4617(5) 0.0658(14) Uani 1 d . .
C5 C 0.6410(9) 0.4245(7) 0.6287(6) 0.118(3) Uani 1 d . .
H5A H 0.7180 0.4698 0.6273 0.178 Uiso 1 calc R .
H5B H 0.6776 0.3638 0.6743 0.178 Uiso 1 calc R .
H5C H 0.5768 0.4583 0.6678 0.178 Uiso 1 calc R .
C6 C 0.2669(5) 0.5750(4) 0.3999(5) 0.0519(12) Uani 1 d . .
C7 C 0.0342(5) 0.6465(5) 0.3887(6) 0.071(2) Uani 1 d . .
C8 C 0.0076(8) 0.6824(8) 0.2558(7) 0.121(3) Uani 1 d . .
H8A H -0.0269 0.6262 0.2008 0.181 Uiso 1 calc R .
H8B H 0.0945 0.7075 0.2419 0.181 Uiso 1 calc R .
H8C H -0.0617 0.7363 0.2405 0.181 Uiso 1 calc R .
C9 C 0.0883(6) 0.7288(6) 0.4815(7) 0.096(2) Uani 1 d . .
H9A H 0.1031 0.7014 0.5636 0.144 Uiso 1 calc R .
H9B H 0.0202 0.7835 0.4696 0.144 Uiso 1 calc R .
H9C H 0.1765 0.7546 0.4710 0.144 Uiso 1 calc R .
C10 C -0.0963(6) 0.5956(6) 0.4138(9) 0.115(3) Uani 1 d . .
H10A H -0.1302 0.5428 0.3535 0.172 Uiso 1 calc R .
H10B H -0.1695 0.6459 0.4083 0.172 Uiso 1 calc R .
H10C H -0.0714 0.5661 0.4954 0.172 Uiso 1 calc R .
C11 C 0.5067(5) 0.4896(4) 0.2890(4) 0.0519(12) Uani 1 d . .
H11A H 0.4542 0.5472 0.2444 0.062 Uiso 1 calc R .
H11B H 0.6051 0.4961 0.2873 0.062 Uiso 1 calc R .
C12 C 0.3964(5) 0.2152(4) 0.0884(5) 0.0544(12) Uani 1 d . .
C13 C 0.4005(7) 0.1675(5) -0.0366(6) 0.080(2) Uani 1 d . .
H13A H 0.4944 0.1740 -0.0475 0.121 Uiso 1 calc R .
H13B H 0.3342 0.2025 -0.1027 0.121 Uiso 1 calc R .
H13C H 0.3755 0.0963 -0.0375 0.121 Uiso 1 calc R .
C14 C 0.5020(6) 0.1560(4) 0.1910(6) 0.076(2) Uani 1 d . .
H14A H 0.5956 0.1620 0.1792 0.114 Uiso 1 calc R .
H14B H 0.4752 0.0851 0.1877 0.114 Uiso 1 calc R .
H14C H 0.5014 0.1839 0.2703 0.114 Uiso 1 calc R .
C15 C 0.2496(6) 0.2057(5) 0.1071(7) 0.085(2) Uani 1 d . .
H15A H 0.1834 0.2427 0.0429 0.128 Uiso 1 calc R .
H15B H 0.2492 0.2336 0.1865 0.128 Uiso 1 calc R .
H15C H 0.2229 0.1348 0.1038 0.128 Uiso 1 calc R .
C16 C 0.6380(4) 0.3646(4) 0.0799(4) 0.0448(10) Uani 1 d . .
C17 C 0.6739(5) 0.3854(4) -0.0285(5) 0.0600(14) Uani 1 d . .
H17 H 0.6021 0.3951 -0.1009 0.072 Uiso 1 calc R .
C18 C 0.8149(6) 0.3926(5) -0.0332(6) 0.072(2) Uani 1 d . .
H18 H 0.8362 0.4069 -0.1078 0.086 Uiso 1 calc R .
C19 C 0.9210(6) 0.3784(5) 0.0721(6) 0.075(2) Uani 1 d . .
H19 H 1.0150 0.3836 0.0692 0.090 Uiso 1 calc R .
C20 C 0.8913(5) 0.3567(5) 0.1817(5) 0.0693(14) Uani 1 d . .
H20 H 0.9641 0.3456 0.2530 0.083 Uiso 1 calc R .
C21 C 0.7503(5) 0.3514(5) 0.1853(4) 0.0575(12) Uani 1 d . .
H21 H 0.7302 0.3386 0.2608 0.069 Uiso 1 calc R .
C22 C 0.3213(4) 0.4315(4) -0.0263(4) 0.0482(11) Uani 1 d . .
C23 C 0.2935(5) 0.4171(4) -0.1537(5) 0.0626(14) Uani 1 d . .
H23 H 0.3453 0.3683 -0.1839 0.075 Uiso 1 calc R .
C24 C 0.1902(6) 0.4737(6) -0.2373(5) 0.080(2) Uani 1 d . .
H24 H 0.1731 0.4623 -0.3221 0.096 Uiso 1 calc R .
C25 C 0.1144(7) 0.5459(6) -0.1939(7) 0.087(2) Uani 1 d . .
H25 H 0.0466 0.5847 -0.2494 0.104 Uiso 1 calc R .
C26 C 0.1374(6) 0.5614(5) -0.0695(6) 0.078(2) Uani 1 d . .
H26 H 0.0844 0.6099 -0.0401 0.094 Uiso 1 calc R .
C27 C 0.2408(5) 0.5042(4) 0.0134(5) 0.0619(14) Uani 1 d . .
H27 H 0.2559 0.5154 0.0980 0.074 Uiso 1 calc R .
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Si C16 108.3(2) . . ?
O1 Si C22 108.1(2) . . ?
C16 Si C22 113.3(2) . . ?
O1 Si C12 105.3(2) . . ?
C16 Si C12 110.5(2) . . ?
C22 Si C12 110.9(2) . . ?
C11 O1 Si 126.8(3) . . ?
C6 O4 C7 120.0(4) . . ?
C6 N C4 128.8(4) . . ?
C6 N C1 118.4(4) . . ?
C4 N C1 112.8(4) . . ?
N C1 C11 112.0(4) . . ?
N C1 C2 102.8(4) . . ?
C11 C1 C2 114.7(4) . . ?
C5 C2 C3 112.3(6) . . ?
C5 C2 C1 111.9(5) . . ?
C3 C2 C1 105.0(4) . . ?
C4 C3 C2 105.9(5) . . ?
O2 C4 N 126.4(5) . . ?
O2 C4 C3 126.1(5) . . ?
N C4 C3 107.5(5) . . ?
O3 C6 O4 126.6(4) . . ?
O3 C6 N 121.8(4) . . ?
O4 C6 N 111.6(4) . . ?
O4 C7 C9 109.6(4) . . ?
O4 C7 C8 109.1(5) . . ?
C9 C7 C8 113.4(7) . . ?
O4 C7 C10 101.5(5) . . ?
C9 C7 C10 110.2(6) . . ?
C8 C7 C10 112.2(6) . . ?
O1 C11 C1 108.7(4) . . ?
C15 C12 C14 109.4(5) . . ?
C15 C12 C13 110.2(5) . . ?
C14 C12 C13 107.6(5) . . ?
C15 C12 Si 110.7(4) . . ?
C14 C12 Si 109.1(3) . . ?
C13 C12 Si 109.7(4) . . ?
C17 C16 C21 116.3(4) . . ?
C17 C16 Si 124.5(3) . . ?
C21 C16 Si 119.2(3) . . ?
C16 C17 C18 122.0(5) . . ?
C19 C18 C17 119.5(5) . . ?
C20 C19 C18 120.8(5) . . ?
C19 C20 C21 119.0(5) . . ?
C20 C21 C16 122.3(4) . . ?
C27 C22 C23 116.7(4) . . ?
C27 C22 Si 118.7(4) . . ?
C23 C22 Si 124.5(4) . . ?
C22 C23 C24 121.8(6) . . ?
C25 C24 C23 119.5(6) . . ?
C26 C25 C24 120.4(6) . . ?
C25 C26 C27 119.6(6) . . ?
C22 C27 C26 122.0(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si O1 1.643(3) . ?
Si C16 1.863(4) . ?
Si C22 1.885(5) . ?
Si C12 1.888(5) . ?
O1 C11 1.436(6) . ?
O2 C4 1.199(6) . ?
O3 C6 1.195(6) . ?
O4 C6 1.321(5) . ?
O4 C7 1.482(6) . ?
N C6 1.392(6) . ?
N C4 1.402(7) . ?
N C1 1.472(6) . ?
C1 C11 1.495(6) . ?
C1 C2 1.537(7) . ?
C2 C5 1.520(8) . ?
C2 C3 1.521(8) . ?
C3 C4 1.496(8) . ?
C7 C9 1.490(8) . ?
C7 C8 1.513(10) . ?
C7 C10 1.528(9) . ?
C12 C15 1.507(7) . ?
C12 C14 1.535(7) . ?
C12 C13 1.539(7) . ?
C16 C17 1.374(6) . ?
C16 C21 1.393(6) . ?
C17 C18 1.394(7) . ?
C18 C19 1.361(8) . ?
C19 C20 1.361(7) . ?
C20 C21 1.390(6) . ?
C22 C27 1.378(7) . ?
C22 C23 1.390(7) . ?
C23 C24 1.393(8) . ?
C24 C25 1.364(10) . ?
C25 C26 1.364(9) . ?
C26 C27 1.394(7) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 Si O1 C11 49.6(4) . . . . ?
C22 Si O1 C11 -73.5(4) . . . . ?
C12 Si O1 C11 167.8(3) . . . . ?
C6 N C1 C11 -74.9(5) . . . . ?
C4 N C1 C11 104.7(5) . . . . ?
C6 N C1 C2 161.4(4) . . . . ?
C4 N C1 C2 -18.9(5) . . . . ?
N C1 C2 C5 -97.8(6) . . . . ?
C11 C1 C2 C5 140.4(5) . . . . ?
N C1 C2 C3 24.4(5) . . . . ?
C11 C1 C2 C3 -97.4(5) . . . . ?
C5 C2 C3 C4 99.8(6) . . . . ?
C1 C2 C3 C4 -22.0(5) . . . . ?
C6 N C4 O2 5.3(10) . . . . ?
C1 N C4 O2 -174.3(6) . . . . ?
C6 N C4 C3 -175.0(5) . . . . ?
C1 N C4 C3 5.4(6) . . . . ?
C2 C3 C4 O2 -169.5(6) . . . . ?
C2 C3 C4 N 10.9(6) . . . . ?
C7 O4 C6 O3 -1.2(8) . . . . ?
C7 O4 C6 N 178.0(4) . . . . ?
C4 N C6 O3 179.5(5) . . . . ?
C1 N C6 O3 -0.9(7) . . . . ?
C4 N C6 O4 0.3(7) . . . . ?
C1 N C6 O4 179.9(4) . . . . ?
C6 O4 C7 C9 -61.8(7) . . . . ?
C6 O4 C7 C8 62.9(6) . . . . ?
C6 O4 C7 C10 -178.4(5) . . . . ?
Si O1 C11 C1 -172.6(3) . . . . ?
N C1 C11 O1 -63.1(5) . . . . ?
C2 C1 C11 O1 53.6(5) . . . . ?
O1 Si C12 C15 59.8(4) . . . . ?
C16 Si C12 C15 176.5(4) . . . . ?
C22 Si C12 C15 -56.9(5) . . . . ?
O1 Si C12 C14 -60.6(4) . . . . ?
C16 Si C12 C14 56.1(4) . . . . ?
C22 Si C12 C14 -177.4(4) . . . . ?
O1 Si C12 C13 -178.3(3) . . . . ?
C16 Si C12 C13 -61.6(4) . . . . ?
C22 Si C12 C13 65.0(4) . . . . ?
O1 Si C16 C17 -147.3(4) . . . . ?
C22 Si C16 C17 -27.3(5) . . . . ?
C12 Si C16 C17 97.8(5) . . . . ?
O1 Si C16 C21 32.4(5) . . . . ?
C22 Si C16 C21 152.3(4) . . . . ?
C12 Si C16 C21 -82.5(5) . . . . ?
C21 C16 C17 C18 0.3(8) . . . . ?
Si C16 C17 C18 -180.0(5) . . . . ?
C16 C17 C18 C19 0.1(9) . . . . ?
C17 C18 C19 C20 0.4(10) . . . . ?
C18 C19 C20 C21 -1.4(10) . . . . ?
C19 C20 C21 C16 1.9(10) . . . . ?
C17 C16 C21 C20 -1.3(8) . . . . ?
Si C16 C21 C20 179.0(5) . . . . ?
O1 Si C22 C27 -2.6(4) . . . . ?
C16 Si C22 C27 -122.6(4) . . . . ?
C12 Si C22 C27 112.4(4) . . . . ?
O1 Si C22 C23 -178.8(4) . . . . ?
C16 Si C22 C23 61.1(5) . . . . ?
C12 Si C22 C23 -63.8(5) . . . . ?
C27 C22 C23 C24 0.5(8) . . . . ?
Si C22 C23 C24 176.8(4) . . . . ?
C22 C23 C24 C25 0.4(9) . . . . ?
C23 C24 C25 C26 -1.2(10) . . . . ?
C24 C25 C26 C27 1.1(10) . . . . ?
C23 C22 C27 C26 -0.6(8) . . . . ?
Si C22 C27 C26 -177.2(4) . . . . ?
C25 C26 C27 C22 -0.1(9) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9125960
