#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/16/7151608.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_7151608
loop_
_publ_author_name
'Charrier, Jean-Damien'
'Hadfield, David S.'
'Hitchcock, Peter B.'
'Young, Douglas W.'
_publ_section_title
;
 Synthesis of (2S,3S)-3'-fluoroisoleucine.
;
_journal_issue                   5
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              797
_journal_page_last               802
_journal_paper_doi               10.1039/b316219b
_journal_volume                  2
_journal_year                    2004
_chemical_absolute_configuration syn
_chemical_formula_sum            'C27 H36 F N O4 Si'
_chemical_formula_weight         485.66
_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                 104.99(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.811(7)
_cell_length_b                   13.067(6)
_cell_length_c                   11.121(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      10
_cell_volume                     1377.2(13)
_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     1.54180
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0594
_diffrn_reflns_limit_h_max       11
_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            2277
_diffrn_reflns_theta_max         60.06
_diffrn_reflns_theta_min         4.12
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    1.061
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.061
_refine_ls_goodness_of_fit_obs   1.083
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         2152
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_restrained_S_obs      1.082
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_obs          0.0635
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1053P)²+0.1825P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1749
_refine_ls_wR_factor_obs         0.1634
_reflns_number_observed          1848
_reflns_number_total             2152
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b316219b.txt
_cod_data_source_block           aug398
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1053P)^2^+0.1825P] 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^)+(0.1053P)^2^+0.1825P] 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               7151608
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 0.4528(2) 0.13520(12) 0.09269(13) 0.0412(4) Uani 1 d . .
F F 0.7380(7) 0.2625(6) 0.6405(5) 0.125(2) Uani 1 d . .
O1 O 0.1821(6) 0.1479(5) 0.4559(6) 0.092(2) Uani 1 d . .
O2 O 0.1374(5) 0.3452(4) 0.4053(5) 0.0609(12) Uani 1 d . .
O3 O 0.3220(5) 0.4358(4) 0.3779(5) 0.0678(14) Uani 1 d . .
O4 O 0.4482(5) 0.1764(3) 0.2321(4) 0.0488(10) Uani 1 d . .
N N 0.3454(5) 0.2674(4) 0.4261(5) 0.0469(12) Uani 1 d . .
C1 C 0.4926(6) 0.2683(5) 0.4235(5) 0.0480(15) Uani 1 d . .
H1 H 0.5389 0.3288 0.4682 0.058 Uiso 1 calc R .
C2 C 0.5531(7) 0.1716(6) 0.4968(5) 0.055(2) Uani 1 d . .
H2 H 0.6198 0.1378 0.4576 0.066 Uiso 1 calc R .
C3 C 0.4253(9) 0.1036(6) 0.4886(7) 0.066(2) Uani 1 d . .
H3A H 0.4197 0.0513 0.4255 0.079 Uiso 1 calc R .
H3B H 0.4320 0.0703 0.5678 0.079 Uiso 1 calc R .
C4 C 0.2980(8) 0.1710(5) 0.4551(6) 0.056(2) Uani 1 d . .
C5 C 0.6239(11) 0.1961(8) 0.6306(7) 0.088(3) Uani 1 d . .
H5A H 0.5560 0.2273 0.6690 0.106 Uiso 1 calc R .
H5B H 0.6568 0.1332 0.6749 0.106 Uiso 1 calc R .
C6 C 0.2659(6) 0.3580(5) 0.3998(6) 0.0479(15) Uani 1 d . .
C7 C 0.0360(7) 0.4310(6) 0.3830(8) 0.066(2) Uani 1 d . .
C8 C 0.0869(10) 0.5112(8) 0.4806(10) 0.097(3) Uani 1 d . .
H8A H 0.1719 0.5415 0.4696 0.146 Uiso 1 calc R .
H8B H 0.1053 0.4804 0.5616 0.146 Uiso 1 calc R .
H8C H 0.0159 0.5631 0.4732 0.146 Uiso 1 calc R .
C9 C -0.0972(9) 0.3828(9) 0.3989(11) 0.105(4) Uani 1 d . .
H9A H -0.1288 0.3316 0.3359 0.158 Uiso 1 calc R .
H9B H -0.1686 0.4344 0.3912 0.158 Uiso 1 calc R .
H9C H -0.0792 0.3517 0.4796 0.158 Uiso 1 calc R .
C10 C 0.0174(11) 0.4696(10) 0.2507(10) 0.115(4) Uani 1 d . .
H10A H -0.0152 0.4147 0.1931 0.172 Uiso 1 calc R .
H10B H 0.1062 0.4944 0.2412 0.172 Uiso 1 calc R .
H10C H -0.0504 0.5242 0.2343 0.172 Uiso 1 calc R .
C11 C 0.5100(6) 0.2694(5) 0.2908(5) 0.0471(14) Uani 1 d . .
H11A H 0.4625 0.3284 0.2458 0.057 Uiso 1 calc R .
H11B H 0.6091 0.2727 0.2921 0.057 Uiso 1 calc R .
C12 C 0.3958(7) -0.0027(5) 0.0889(6) 0.051(2) Uani 1 d . .
C13 C 0.2488(9) -0.0116(6) 0.1048(9) 0.079(2) Uani 1 d . .
H13A H 0.1851 0.0270 0.0407 0.118 Uiso 1 calc R .
H13B H 0.2467 0.0148 0.1848 0.118 Uiso 1 calc R .
H13C H 0.2208 -0.0822 0.0989 0.118 Uiso 1 calc R .
C14 C 0.3993(10) -0.0498(6) -0.0378(7) 0.075(2) Uani 1 d . .
H14A H 0.4930 -0.0444 -0.0486 0.112 Uiso 1 calc R .
H14B H 0.3346 -0.0137 -0.1036 0.112 Uiso 1 calc R .
H14C H 0.3725 -0.1206 -0.0396 0.112 Uiso 1 calc R .
C15 C 0.5000(9) -0.0633(6) 0.1896(8) 0.075(2) Uani 1 d . .
H15A H 0.5932 -0.0567 0.1779 0.113 Uiso 1 calc R .
H15B H 0.4733 -0.1342 0.1842 0.113 Uiso 1 calc R .
H15C H 0.4991 -0.0372 0.2701 0.113 Uiso 1 calc R .
C16 C 0.6386(6) 0.1459(5) 0.0800(5) 0.0451(13) Uani 1 d . .
C17 C 0.6744(8) 0.1709(6) -0.0288(6) 0.057(2) Uani 1 d . .
H17 H 0.6027 0.1840 -0.1002 0.069 Uiso 1 calc R .
C18 C 0.8131(8) 0.1772(7) -0.0353(7) 0.069(2) Uani 1 d . .
H18 H 0.8337 0.1927 -0.1103 0.083 Uiso 1 calc R .
C19 C 0.9190(8) 0.1603(7) 0.0689(8) 0.073(2) Uani 1 d . .
H19 H 1.0126 0.1652 0.0656 0.088 Uiso 1 calc R .
C20 C 0.8877(8) 0.1358(7) 0.1798(7) 0.072(2) Uani 1 d . .
H20 H 0.9598 0.1242 0.2513 0.086 Uiso 1 calc R .
C21 C 0.7494(7) 0.1289(7) 0.1835(6) 0.059(2) Uani 1 d . .
H21 H 0.7294 0.1121 0.2584 0.071 Uiso 1 calc R .
C22 C 0.3242(6) 0.2130(5) -0.0271(6) 0.0460(15) Uani 1 d . .
C23 C 0.2947(8) 0.1978(6) -0.1550(6) 0.063(2) Uani 1 d . .
H23 H 0.3459 0.1492 -0.1860 0.076 Uiso 1 calc R .
C24 C 0.1911(8) 0.2530(8) -0.2373(7) 0.075(2) Uani 1 d . .
H24 H 0.1738 0.2410 -0.3224 0.090 Uiso 1 calc R .
C25 C 0.1143(9) 0.3247(8) -0.1949(9) 0.081(2) Uani 1 d . .
H25 H 0.0433 0.3605 -0.2507 0.098 Uiso 1 calc R .
C26 C 0.1419(8) 0.3441(8) -0.0694(8) 0.081(2) Uani 1 d . .
H26 H 0.0931 0.3954 -0.0402 0.097 Uiso 1 calc R .
C27 C 0.2427(7) 0.2871(6) 0.0128(7) 0.060(2) Uani 1 d . .
H27 H 0.2569 0.2982 0.0977 0.072 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'
F F 0.0727 0.0534 '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
O4 Si C16 108.1(2) . . ?
O4 Si C22 108.2(3) . . ?
C16 Si C22 113.2(3) . . ?
O4 Si C12 104.6(3) . . ?
C16 Si C12 111.1(3) . . ?
C22 Si C12 111.1(3) . . ?
C6 O2 C7 121.2(6) . . ?
C11 O4 Si 126.2(4) . . ?
C6 N C4 127.0(5) . . ?
C6 N C1 119.4(5) . . ?
C4 N C1 113.6(5) . . ?
N C1 C11 112.3(5) . . ?
N C1 C2 103.4(5) . . ?
C11 C1 C2 113.3(5) . . ?
C5 C2 C3 110.3(6) . . ?
C5 C2 C1 111.5(6) . . ?
C3 C2 C1 104.5(5) . . ?
C4 C3 C2 107.1(6) . . ?
O1 C4 N 127.3(7) . . ?
O1 C4 C3 126.4(7) . . ?
N C4 C3 106.3(6) . . ?
F C5 C2 111.4(8) . . ?
O3 C6 O2 128.3(6) . . ?
O3 C6 N 119.5(5) . . ?
O2 C6 N 112.2(6) . . ?
O2 C7 C8 109.0(6) . . ?
O2 C7 C9 103.3(7) . . ?
C8 C7 C9 110.2(7) . . ?
O2 C7 C10 108.7(6) . . ?
C8 C7 C10 113.8(9) . . ?
C9 C7 C10 111.3(8) . . ?
O4 C11 C1 106.9(5) . . ?
C13 C12 C15 110.8(7) . . ?
C13 C12 C14 108.9(7) . . ?
C15 C12 C14 107.0(6) . . ?
C13 C12 Si 111.1(5) . . ?
C15 C12 Si 109.9(5) . . ?
C14 C12 Si 109.0(5) . . ?
C21 C16 C17 116.3(6) . . ?
C21 C16 Si 119.8(5) . . ?
C17 C16 Si 123.9(5) . . ?
C18 C17 C16 122.4(6) . . ?
C19 C18 C17 119.4(7) . . ?
C18 C19 C20 120.0(7) . . ?
C21 C20 C19 119.5(7) . . ?
C20 C21 C16 122.4(6) . . ?
C23 C22 C27 116.0(6) . . ?
C23 C22 Si 124.9(5) . . ?
C27 C22 Si 118.9(5) . . ?
C24 C23 C22 121.8(8) . . ?
C25 C24 C23 120.5(8) . . ?
C24 C25 C26 119.8(8) . . ?
C25 C26 C27 119.5(9) . . ?
C26 C27 C22 122.3(7) . . ?
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 O4 1.654(4) . ?
Si C16 1.869(6) . ?
Si C22 1.879(6) . ?
Si C12 1.884(6) . ?
F C5 1.398(12) . ?
O1 C4 1.178(8) . ?
O2 C6 1.289(7) . ?
O2 C7 1.477(9) . ?
O3 C6 1.210(8) . ?
O4 C11 1.437(7) . ?
N C6 1.406(8) . ?
N C4 1.409(9) . ?
N C1 1.453(7) . ?
C1 C11 1.529(8) . ?
C1 C2 1.537(9) . ?
C2 C5 1.504(10) . ?
C2 C3 1.520(10) . ?
C3 C4 1.495(10) . ?
C7 C8 1.498(11) . ?
C7 C9 1.501(12) . ?
C7 C10 1.521(13) . ?
C12 C13 1.502(10) . ?
C12 C15 1.529(10) . ?
C12 C14 1.546(9) . ?
C16 C21 1.382(9) . ?
C16 C17 1.384(8) . ?
C17 C18 1.383(10) . ?
C18 C19 1.360(11) . ?
C19 C20 1.383(10) . ?
C20 C21 1.371(9) . ?
C22 C23 1.391(9) . ?
C22 C27 1.399(10) . ?
C23 C24 1.381(11) . ?
C24 C25 1.362(13) . ?
C25 C26 1.375(12) . ?
C26 C27 1.379(10) . ?
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 O4 C11 47.6(5) . . . . ?
C22 Si O4 C11 -75.4(5) . . . . ?
C12 Si O4 C11 166.0(5) . . . . ?
C6 N C1 C11 -75.6(7) . . . . ?
C4 N C1 C11 103.9(6) . . . . ?
C6 N C1 C2 161.9(5) . . . . ?
C4 N C1 C2 -18.6(7) . . . . ?
N C1 C2 C5 -96.6(7) . . . . ?
C11 C1 C2 C5 141.6(7) . . . . ?
N C1 C2 C3 22.4(6) . . . . ?
C11 C1 C2 C3 -99.4(6) . . . . ?
C5 C2 C3 C4 100.4(7) . . . . ?
C1 C2 C3 C4 -19.5(7) . . . . ?
C6 N C4 O1 4.4(11) . . . . ?
C1 N C4 O1 -175.0(7) . . . . ?
C6 N C4 C3 -174.0(6) . . . . ?
C1 N C4 C3 6.6(7) . . . . ?
C2 C3 C4 O1 -169.7(7) . . . . ?
C2 C3 C4 N 8.7(7) . . . . ?
C3 C2 C5 F -177.2(7) . . . . ?
C1 C2 C5 F -61.7(9) . . . . ?
C7 O2 C6 O3 0.3(10) . . . . ?
C7 O2 C6 N 178.9(5) . . . . ?
C4 N C6 O3 179.1(6) . . . . ?
C1 N C6 O3 -1.5(9) . . . . ?
C4 N C6 O2 0.3(9) . . . . ?
C1 N C6 O2 179.7(5) . . . . ?
C6 O2 C7 C8 -62.6(9) . . . . ?
C6 O2 C7 C9 -179.8(7) . . . . ?
C6 O2 C7 C10 61.9(9) . . . . ?
Si O4 C11 C1 -173.7(4) . . . . ?
N C1 C11 O4 -62.2(7) . . . . ?
C2 C1 C11 O4 54.5(7) . . . . ?
O4 Si C12 C13 61.1(6) . . . . ?
C16 Si C12 C13 177.5(5) . . . . ?
C22 Si C12 C13 -55.4(6) . . . . ?
O4 Si C12 C15 -61.9(5) . . . . ?
C16 Si C12 C15 54.5(6) . . . . ?
C22 Si C12 C15 -178.4(5) . . . . ?
O4 Si C12 C14 -178.9(5) . . . . ?
C16 Si C12 C14 -62.5(6) . . . . ?
C22 Si C12 C14 64.6(5) . . . . ?
O4 Si C16 C21 34.9(7) . . . . ?
C22 Si C16 C21 154.7(6) . . . . ?
C12 Si C16 C21 -79.4(7) . . . . ?
O4 Si C16 C17 -144.8(6) . . . . ?
C22 Si C16 C17 -25.0(7) . . . . ?
C12 Si C16 C17 100.9(6) . . . . ?
C21 C16 C17 C18 1.0(11) . . . . ?
Si C16 C17 C18 -179.3(6) . . . . ?
C16 C17 C18 C19 -1.4(12) . . . . ?
C17 C18 C19 C20 0.9(13) . . . . ?
C18 C19 C20 C21 0.0(13) . . . . ?
C19 C20 C21 C16 -0.3(13) . . . . ?
C17 C16 C21 C20 -0.2(12) . . . . ?
Si C16 C21 C20 -179.9(7) . . . . ?
O4 Si C22 C23 -177.3(6) . . . . ?
C16 Si C22 C23 62.9(7) . . . . ?
C12 Si C22 C23 -62.9(6) . . . . ?
O4 Si C22 C27 -2.5(6) . . . . ?
C16 Si C22 C27 -122.3(5) . . . . ?
C12 Si C22 C27 111.8(5) . . . . ?
C27 C22 C23 C24 0.2(10) . . . . ?
Si C22 C23 C24 175.1(6) . . . . ?
C22 C23 C24 C25 0.0(13) . . . . ?
C23 C24 C25 C26 1.5(14) . . . . ?
C24 C25 C26 C27 -3.2(14) . . . . ?
C25 C26 C27 C22 3.6(13) . . . . ?
C23 C22 C27 C26 -2.0(11) . . . . ?
Si C22 C27 C26 -177.2(6) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10330994
