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#$Date: 2016-03-22 10:29:25 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178872 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/01/4110169.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_4110169
loop_
_publ_author_name
'Erin M. Forbeck'
'Cory D. Evans'
'John A. Gilleran'
'Pixu Li'
'Madeleine M. Joullié'
_publ_section_title
;
 A Regio- and Stereoselective Approach to Quaternary Centers from Chiral
 Trisubstituted Aziridines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14463
_journal_page_last               14469
_journal_paper_doi               10.1021/ja0758077
_journal_volume                  129
_journal_year                    2007
_chemical_formula_sum            'C24 H31 Br N2 O6 S Si'
_chemical_formula_weight         583.57
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.634(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.5237(14)
_cell_length_b                   10.5852(13)
_cell_length_c                   12.6006(19)
_cell_measurement_temperature    143(1)
_cell_volume                     1358.1(3)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0124
_diffrn_reflns_av_sigmaI/netI    0.0625
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6569
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.55
_exptl_absorpt_coefficient_mu    1.675
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8058
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_F_000             604
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.004(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.807
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         4033
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.807
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0203
_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)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0375
_refine_ls_wR_factor_ref         0.0390
_reflns_number_gt                3207
_reflns_number_total             4033
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0758077si20070808_042846.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21 '
_cod_database_code               4110169
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
Br1 Br 0.57181(3) 0.87487(3) 1.01422(2) 0.04088(9) Uani 1 1 d .
S1 S 0.30364(6) 0.31617(6) 0.49164(5) 0.02005(16) Uani 1 1 d .
Si1 Si -0.07846(7) 0.61540(8) 0.20659(6) 0.02119(18) Uani 1 1 d .
O2 O 0.60807(18) 0.46080(19) 0.37104(15) 0.0372(5) Uani 1 1 d .
O1 O 0.41886(17) 0.5337(2) 0.38056(15) 0.0356(5) Uani 1 1 d .
O3 O 0.33626(16) 0.26641(17) 0.39525(14) 0.0266(5) Uani 1 1 d .
O4 O 0.24927(15) 0.23508(17) 0.56030(14) 0.0247(4) Uani 1 1 d .
O5 O 0.26087(14) 0.53047(16) 0.66115(13) 0.0181(4) Uani 1 1 d .
O6 O 0.01450(16) 0.57720(18) 0.32940(14) 0.0230(5) Uani 1 1 d .
N1 N 0.5236(2) 0.4784(2) 0.41999(18) 0.0258(6) Uani 1 1 d .
N2 N 0.20199(17) 0.42855(19) 0.45093(15) 0.0174(5) Uani 1 1 d .
H2 H 0.2071 0.4666 0.3918 0.023 Uiso 1 1 calc R
C1 C 0.45636(19) 0.3720(3) 0.57535(17) 0.0175(5) Uani 1 1 d .
C2 C 0.5503(2) 0.4344(2) 0.53454(19) 0.0186(6) Uani 1 1 d .
C3 C 0.6735(2) 0.4605(3) 0.6001(2) 0.0270(7) Uani 1 1 d .
H3 H 0.7358 0.5000 0.5707 0.036 Uiso 1 1 calc R
C4 C 0.7036(2) 0.4280(3) 0.7086(2) 0.0315(8) Uani 1 1 d .
H4 H 0.7860 0.4469 0.7536 0.042 Uiso 1 1 calc R
C5 C 0.6122(2) 0.3673(4) 0.75144(19) 0.0312(7) Uani 1 1 d .
H5 H 0.6332 0.3454 0.8253 0.042 Uiso 1 1 calc R
C6 C 0.4890(2) 0.3384(3) 0.6853(2) 0.0270(7) Uani 1 1 d .
H6 H 0.4281 0.2964 0.7148 0.036 Uiso 1 1 calc R
C7 C 0.1013(2) 0.4741(3) 0.50264(18) 0.0164(6) Uani 1 1 d .
H7 H 0.0797 0.4045 0.5463 0.022 Uiso 1 1 calc R
C8 C 0.1501(2) 0.5850(3) 0.58115(19) 0.0176(6) Uani 1 1 d .
C9 C 0.3312(2) 0.6094(3) 0.74213(19) 0.0173(6) Uani 1 1 d .
C10 C 0.4460(2) 0.6654(3) 0.7302(2) 0.0230(7) Uani 1 1 d .
H10 H 0.4739 0.6511 0.6668 0.031 Uiso 1 1 calc R
C11 C 0.5189(2) 0.7417(3) 0.8111(2) 0.0248(7) Uani 1 1 d .
H11 H 0.5961 0.7787 0.8029 0.033 Uiso 1 1 calc R
C12 C 0.4769(2) 0.7631(3) 0.9047(2) 0.0234(7) Uani 1 1 d .
C13 C 0.3637(2) 0.7069(3) 0.9190(2) 0.0258(7) Uani 1 1 d .
H13 H 0.3367 0.7212 0.9828 0.034 Uiso 1 1 calc R
C14 C 0.2912(2) 0.6295(3) 0.83807(19) 0.0203(6) Uani 1 1 d .
H14 H 0.2156 0.5907 0.8475 0.027 Uiso 1 1 calc R
C15 C -0.0207(2) 0.5010(3) 0.41016(18) 0.0187(6) Uani 1 1 d .
H15A H -0.0585 0.4221 0.3776 0.025 Uiso 1 1 calc R
H15B H -0.0859 0.5443 0.4392 0.025 Uiso 1 1 calc R
C16 C -0.0862(3) 0.7905(3) 0.2011(2) 0.0342(8) Uani 1 1 d .
H16A H -0.1432 0.8202 0.2443 0.051 Uiso 1 1 calc R
H16B H -0.1196 0.8173 0.1264 0.051 Uiso 1 1 calc R
H16C H 0.0002 0.8246 0.2296 0.051 Uiso 1 1 calc R
C17 C -0.2459(2) 0.5471(3) 0.1843(2) 0.0387(8) Uani 1 1 d .
H17A H -0.2404 0.4565 0.1843 0.058 Uiso 1 1 calc R
H17B H -0.2996 0.5754 0.1151 0.058 Uiso 1 1 calc R
H17C H -0.2842 0.5740 0.2421 0.058 Uiso 1 1 calc R
C18 C 0.0080(3) 0.5511(3) 0.1034(2) 0.0276(7) Uani 1 1 d .
C19 C 0.1370(3) 0.6236(3) 0.1121(2) 0.0444(9) Uani 1 1 d .
H19A H 0.1895 0.6207 0.1864 0.067 Uiso 1 1 calc R
H19B H 0.1176 0.7099 0.0906 0.067 Uiso 1 1 calc R
H19C H 0.1844 0.5853 0.0646 0.067 Uiso 1 1 calc R
C20 C -0.0797(3) 0.5637(3) -0.0137(2) 0.0451(9) Uani 1 1 d .
H20A H -0.1066 0.6501 -0.0273 0.068 Uiso 1 1 calc R
H20B H -0.1559 0.5111 -0.0216 0.068 Uiso 1 1 calc R
H20C H -0.0315 0.5377 -0.0652 0.068 Uiso 1 1 calc R
C21 C 0.0409(3) 0.4106(3) 0.1274(2) 0.0476(9) Uani 1 1 d .
H21A H 0.0816 0.3773 0.0732 0.071 Uiso 1 1 calc R
H21B H -0.0384 0.3646 0.1251 0.071 Uiso 1 1 calc R
H21C H 0.0999 0.4022 0.1988 0.071 Uiso 1 1 calc R
C22 C 0.1929(2) 0.7007(2) 0.5257(2) 0.0227(7) Uani 1 1 d .
H22A H 0.2284 0.7635 0.5801 0.034 Uiso 1 1 calc R
H22B H 0.1185 0.7349 0.4731 0.034 Uiso 1 1 calc R
H22C H 0.2587 0.6760 0.4891 0.034 Uiso 1 1 calc R
C23 C 0.0460(2) 0.6215(3) 0.63617(19) 0.0193(6) Uani 1 1 d .
C24 C -0.0360(3) 0.6502(3) 0.6783(2) 0.0246(7) Uani 1 1 d .
H24 H -0.1017 0.6732 0.7120 0.033 Uiso 1 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 0.0033 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'
S S 0.1246 0.1234 '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'
Br Br -0.2901 2.4595 '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
O4 S1 O3 120.31(11)
O4 S1 N2 107.61(10)
O3 S1 N2 106.52(11)
O4 S1 C1 106.15(11)
O3 S1 C1 104.37(10)
N2 S1 C1 111.92(12)
O6 Si1 C16 106.77(12)
O6 Si1 C17 111.05(11)
C16 Si1 C17 110.61(14)
O6 Si1 C18 106.30(11)
C16 Si1 C18 110.97(13)
C17 Si1 C18 110.99(13)
C9 O5 C8 117.26(19)
C15 O6 Si1 127.48(15)
O2 N1 O1 124.0(2)
O2 N1 C2 117.7(2)
O1 N1 C2 118.3(2)
C7 N2 S1 127.34(16)
C6 C1 C2 118.1(2)
C6 C1 S1 117.63(19)
C2 C1 S1 123.82(17)
C3 C2 C1 121.5(2)
C3 C2 N1 116.2(2)
C1 C2 N1 122.3(2)
C4 C3 C2 119.6(3)
C3 C4 C5 120.1(2)
C4 C5 C6 120.5(2)
C5 C6 C1 120.1(2)
N2 C7 C15 106.63(18)
N2 C7 C8 112.17(18)
C15 C7 C8 115.4(2)
O5 C8 C23 109.61(18)
O5 C8 C22 110.90(19)
C23 C8 C22 110.0(2)
O5 C8 C7 102.8(2)
C23 C8 C7 109.40(19)
C22 C8 C7 113.90(19)
O5 C9 C10 119.83(19)
O5 C9 C14 120.7(2)
C10 C9 C14 119.4(2)
C11 C10 C9 120.6(2)
C10 C11 C12 119.4(2)
C11 C12 C13 121.0(2)
C11 C12 Br1 120.0(2)
C13 C12 Br1 119.00(19)
C14 C13 C12 119.5(2)
C13 C14 C9 120.1(2)
O6 C15 C7 109.38(18)
C20 C18 C19 109.3(2)
C20 C18 C21 108.8(2)
C19 C18 C21 108.5(3)
C20 C18 Si1 110.63(19)
C19 C18 Si1 109.9(2)
C21 C18 Si1 109.67(17)
C24 C23 C8 179.4(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C12 1.900(3)
S1 O4 1.4362(17)
S1 O3 1.4425(16)
S1 N2 1.595(2)
S1 C1 1.786(2)
Si1 O6 1.6584(19)
Si1 C16 1.856(3)
Si1 C17 1.859(3)
Si1 C18 1.891(2)
O2 N1 1.218(2)
O1 N1 1.236(3)
O5 C9 1.381(3)
O5 C8 1.454(3)
O6 C15 1.419(3)
N1 C2 1.475(3)
N2 C7 1.459(3)
C1 C6 1.387(3)
C1 C2 1.391(3)
C2 C3 1.378(3)
C3 C4 1.368(3)
C4 C5 1.375(3)
C5 C6 1.387(3)
C7 C15 1.527(3)
C7 C8 1.538(3)
C8 C23 1.488(3)
C8 C22 1.533(3)
C9 C10 1.388(3)
C9 C14 1.393(3)
C10 C11 1.373(3)
C11 C12 1.378(3)
C12 C13 1.384(3)
C13 C14 1.378(4)
C18 C20 1.536(3)
C18 C19 1.539(4)
C18 C21 1.539(4)
C23 C24 1.162(3)
