#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:14:47 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180295 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/09/7150958.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_7150958
loop_
_publ_author_name
'Pattenden, Gerald'
'Rescourio, Gwenaëlla'
_publ_section_title
;
 A new synthetic approach to (+)-lactacystin based on radical
 cyclisation of enantiopure α-ethynyl substituted serine derivatives
 to 4-methylenepyrrolidinones
;
_journal_issue                   18
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              3428
_journal_page_last               3438
_journal_paper_doi               10.1039/b806681g
_journal_volume                  6
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H20 Cl3 N O2 Si'
_chemical_formula_sum            'C13 H20 Cl3 N O2 Si'
_chemical_formula_weight         356.74
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.030(2)
_cell_length_b                   10.027(2)
_cell_length_c                   22.837(5)
_cell_measurement_reflns_used    1366
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.95
_cell_measurement_theta_min      2.7
_cell_volume                     1838.8(7)
_computing_cell_refinement       'Bruker SAINT version 6.36a (Bruker, 2000)'
_computing_data_collection       'Bruker SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 2001)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material
'SHELXL-97; enCIFer (CCDC, 2003); PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       omega
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.061
_diffrn_reflns_av_sigmaI/netI    0.101
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9295
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.22
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.564
_exptl_absorpt_correction_T_max  0.889
_exptl_absorpt_correction_T_min  0.785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SHELXTL version 6.12; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.18
_refine_diff_density_rms         0.04
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.77
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3231
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      0.80
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.007P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0447
_refine_ls_wR_factor_ref         0.0488
_reflns_number_gt                1948
_reflns_number_total             3231
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b806681g.txt
_cod_data_source_block           ISOXCL
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        1838.8(11)
_cod_database_code               7150958
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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
O1 O 0.1213(3) -0.04550(19) 0.82037(8) 0.0352(6) Uani 1 1 d . . .
C2 C 0.2398(4) -0.0696(3) 0.86074(14) 0.0262(8) Uani 1 1 d . A .
N3 N 0.2036(3) -0.0787(2) 0.91410(11) 0.0263(6) Uani 1 1 d . . .
C4 C 0.0226(4) -0.0497(3) 0.91741(12) 0.0256(7) Uani 1 1 d . . .
C5 C -0.0335(4) -0.0487(3) 0.85310(11) 0.0352(9) Uani 1 1 d . . .
H5A H -0.0972 -0.1282 0.8438 0.042 Uiso 1 1 calc R . .
H5B H -0.1008 0.0293 0.8447 0.042 Uiso 1 1 calc R . .
C6 C 0.4135(4) -0.0815(3) 0.83589(11) 0.0316(8) Uani 1 1 d D . .
C7 C -0.0009(4) 0.0874(2) 0.94666(12) 0.0386(8) Uani 1 1 d . . .
H7A H -0.1186 0.1049 0.9525 0.046 Uiso 1 1 calc R . .
H7B H 0.0534 0.0883 0.9846 0.046 Uiso 1 1 calc R . .
O8 O 0.0694(2) 0.18704(16) 0.91009(8) 0.0412(6) Uani 1 1 d . . .
Si9 Si -0.00389(11) 0.34204(8) 0.90887(4) 0.0354(2) Uani 1 1 d . . .
C10 C 0.1313(4) 0.4304(3) 0.85525(13) 0.0390(9) Uani 1 1 d . . .
C11 C 0.1329(4) 0.3548(3) 0.79661(13) 0.0565(11) Uani 1 1 d . . .
H11A H 0.2014 0.4019 0.7690 0.085 Uiso 1 1 calc R . .
H11B H 0.0214 0.3486 0.7817 0.085 Uiso 1 1 calc R . .
H11C H 0.1768 0.2668 0.8025 0.085 Uiso 1 1 calc R . .
C12 C 0.3124(4) 0.4369(4) 0.87786(15) 0.0602(11) Uani 1 1 d . . .
H12A H 0.3804 0.4832 0.8499 0.090 Uiso 1 1 calc R . .
H12B H 0.3543 0.3481 0.8832 0.090 Uiso 1 1 calc R . .
H12C H 0.3150 0.4835 0.9146 0.090 Uiso 1 1 calc R . .
C13 C 0.0653(5) 0.5729(3) 0.84440(14) 0.0736(13) Uani 1 1 d . . .
H13A H 0.1352 0.6171 0.8164 0.110 Uiso 1 1 calc R . .
H13B H 0.0661 0.6219 0.8805 0.110 Uiso 1 1 calc R . .
H13C H -0.0464 0.5683 0.8296 0.110 Uiso 1 1 calc R . .
C14 C 0.0086(4) 0.4120(3) 0.98382(11) 0.0571(10) Uani 1 1 d . . .
H14A H 0.1225 0.4127 0.9965 0.086 Uiso 1 1 calc R . .
H14B H -0.0563 0.3581 1.0100 0.086 Uiso 1 1 calc R . .
H14C H -0.0341 0.5015 0.9838 0.086 Uiso 1 1 calc R . .
C15 C -0.2243(3) 0.3404(3) 0.88480(14) 0.0568(10) Uani 1 1 d . . .
H15A H -0.2312 0.3050 0.8458 0.085 Uiso 1 1 calc R . .
H15B H -0.2674 0.4297 0.8852 0.085 Uiso 1 1 calc R . .
H15C H -0.2884 0.2857 0.9109 0.085 Uiso 1 1 calc R . .
C16 C -0.0637(4) -0.1483(3) 0.95355(12) 0.0308(8) Uani 1 1 d . . .
C17 C -0.1365(4) -0.2201(3) 0.98428(14) 0.0418(10) Uani 1 1 d . . .
H17 H -0.1947 -0.2776 1.0089 0.050 Uiso 1 1 calc R . .
Cl1 Cl 0.5408(11) -0.1713(6) 0.8833(3) 0.0672(19) Uani 0.50 1 d PD A 1
Cl2 Cl 0.4100(7) -0.1486(4) 0.76585(15) 0.0758(13) Uani 0.50 1 d PD A 1
Cl3 Cl 0.4941(5) 0.0846(3) 0.83252(11) 0.0552(8) Uani 0.50 1 d PD A 1
Cl1' Cl 0.5568(11) -0.1267(6) 0.8895(3) 0.0535(15) Uani 0.50 1 d PD A 2
Cl2' Cl 0.4197(6) -0.2112(3) 0.78173(16) 0.0536(10) Uani 0.50 1 d PD A 2
Cl3' Cl 0.4718(6) 0.0667(3) 0.80157(11) 0.0613(10) Uani 0.50 1 d PD A 2
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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C2 O1 C5 104.4(2) . . ?
N3 C2 O1 120.9(3) . . ?
N3 C2 C6 124.9(3) . . ?
O1 C2 C6 114.2(3) . . ?
C2 N3 C4 105.2(2) . . ?
C16 C4 N3 111.1(2) . . ?
C16 C4 C5 113.9(3) . . ?
N3 C4 C5 103.9(2) . . ?
C16 C4 C7 107.5(2) . . ?
N3 C4 C7 108.5(2) . . ?
C5 C4 C7 111.9(2) . . ?
O1 C5 C4 104.0(2) . . ?
O1 C5 H5A 111.0 . . ?
C4 C5 H5A 111.0 . . ?
O1 C5 H5B 111.0 . . ?
C4 C5 H5B 111.0 . . ?
H5A C5 H5B 109.0 . . ?
C2 C6 Cl1 110.5(4) . . ?
C2 C6 Cl2 111.2(3) . . ?
C2 C6 Cl3 106.1(2) . . ?
C2 C6 Cl1' 111.5(4) . . ?
C2 C6 Cl2' 110.0(3) . . ?
C2 C6 Cl3' 110.4(3) . . ?
Cl1 C6 Cl2 112.5(3) . . ?
Cl1 C6 Cl3 107.2(3) . . ?
Cl2 C6 Cl3 109.1(2) . . ?
Cl1' C6 Cl2' 106.1(3) . . ?
Cl1' C6 Cl3' 111.2(3) . . ?
Cl2' C6 Cl3' 107.45(19) . . ?
O8 C7 C4 108.9(2) . . ?
O8 C7 H7A 109.9 . . ?
C4 C7 H7A 109.9 . . ?
O8 C7 H7B 109.9 . . ?
C4 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C7 O8 Si9 121.83(17) . . ?
O8 Si9 C14 108.63(12) . . ?
O8 Si9 C15 109.56(14) . . ?
C14 Si9 C15 109.21(15) . . ?
O8 Si9 C10 104.47(13) . . ?
C14 Si9 C10 113.33(15) . . ?
C15 Si9 C10 111.48(15) . . ?
C11 C10 C13 108.6(3) . . ?
C11 C10 C12 107.7(3) . . ?
C13 C10 C12 109.8(3) . . ?
C11 C10 Si9 110.0(2) . . ?
C13 C10 Si9 110.2(2) . . ?
C12 C10 Si9 110.5(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
Si9 C14 H14A 109.5 . . ?
Si9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
Si9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
Si9 C15 H15A 109.5 . . ?
Si9 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
Si9 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C4 175.7(3) . . ?
C16 C17 H17 180.0 . . ?
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
O1 C2 1.347(3) . ?
O1 C5 1.451(3) . ?
C2 N3 1.256(3) . ?
C2 C6 1.511(4) . ?
N3 C4 1.484(3) . ?
C4 C16 1.463(4) . ?
C4 C5 1.536(3) . ?
C4 C7 1.540(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 Cl1 1.740(5) . ?
C6 Cl2 1.735(4) . ?
C6 Cl3 1.789(4) . ?
C6 Cl1' 1.740(5) . ?
C6 Cl2' 1.795(4) . ?
C6 Cl3' 1.744(4) . ?
C7 O8 1.419(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
O8 Si9 1.6621(18) . ?
Si9 C14 1.853(3) . ?
Si9 C15 1.853(3) . ?
Si9 C10 1.861(3) . ?
C10 C11 1.539(4) . ?
C10 C13 1.544(4) . ?
C10 C12 1.544(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
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 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.163(4) . ?
C17 H17 0.9300 . ?
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
C5 O1 C2 N3 -5.3(4) . . . . ?
C5 O1 C2 C6 175.6(3) . . . . ?
O1 C2 N3 C4 -3.4(4) . . . . ?
C6 C2 N3 C4 175.6(3) . . . . ?
C2 N3 C4 C16 132.8(3) . . . . ?
C2 N3 C4 C5 10.0(3) . . . . ?
C2 N3 C4 C7 -109.2(3) . . . . ?
C2 O1 C5 C4 11.0(3) . . . . ?
C16 C4 C5 O1 -133.8(2) . . . . ?
N3 C4 C5 O1 -12.8(3) . . . . ?
C7 C4 C5 O1 104.0(3) . . . . ?
N3 C2 C6 Cl2 149.0(3) . . . . ?
O1 C2 C6 Cl2 -32.0(3) . . . . ?
N3 C2 C6 Cl1 23.3(5) . . . . ?
O1 C2 C6 Cl1 -157.7(3) . . . . ?
N3 C2 C6 Cl1' 6.1(5) . . . . ?
O1 C2 C6 Cl1' -174.8(3) . . . . ?
N3 C2 C6 Cl3' -118.0(3) . . . . ?
O1 C2 C6 Cl3' 61.1(3) . . . . ?
N3 C2 C6 Cl3 -92.6(4) . . . . ?
O1 C2 C6 Cl3 86.5(3) . . . . ?
N3 C2 C6 Cl2' 123.6(3) . . . . ?
O1 C2 C6 Cl2' -57.4(3) . . . . ?
C16 C4 C7 O8 -175.1(2) . . . . ?
N3 C4 C7 O8 64.6(3) . . . . ?
C5 C4 C7 O8 -49.4(3) . . . . ?
C4 C7 O8 Si9 150.5(2) . . . . ?
C7 O8 Si9 C14 58.2(2) . . . . ?
C7 O8 Si9 C15 -61.0(2) . . . . ?
C7 O8 Si9 C10 179.4(2) . . . . ?
O8 Si9 C10 C11 54.0(2) . . . . ?
C14 Si9 C10 C11 172.1(2) . . . . ?
C15 Si9 C10 C11 -64.2(3) . . . . ?
O8 Si9 C10 C13 173.8(2) . . . . ?
C14 Si9 C10 C13 -68.2(3) . . . . ?
C15 Si9 C10 C13 55.5(3) . . . . ?
O8 Si9 C10 C12 -64.8(3) . . . . ?
C14 Si9 C10 C12 53.3(3) . . . . ?
C15 Si9 C10 C12 177.0(2) . . . . ?
