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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/4/11/01/4110175.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_4110175
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            'C26 H24 N2 O7 S'
_chemical_formula_weight         508.53
_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                 99.94(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.551(6)
_cell_length_b                   11.819(9)
_cell_length_c                   12.611(8)
_cell_measurement_temperature    143(1)
_cell_volume                     1255.4(15)
_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 0.982
_diffrn_measured_fraction_theta_max 0.982
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7861
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         2.68
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7755
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.055
_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   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         3849
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0575P)²+0.0740P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.1014
_reflns_number_gt                3585
_reflns_number_total             3849
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0758077si20070808_043211.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21 '
_cod_database_code               4110175
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
S1 S 0.22820(8) 0.72307(6) -0.15621(5) 0.02452(18) Uani 1 1 d .
O1 O 0.3238(3) 0.47099(18) -0.13264(17) 0.0375(5) Uani 1 1 d .
O2 O 0.3911(3) 0.44320(19) -0.28704(17) 0.0384(6) Uani 1 1 d .
O3 O 0.2017(3) 0.84185(17) -0.15461(16) 0.0320(5) Uani 1 1 d .
O4 O 0.1349(2) 0.65420(17) -0.23656(15) 0.0309(5) Uani 1 1 d .
O5 O 0.2126(2) 0.79821(17) 0.22565(14) 0.0262(4) Uani 1 1 d .
O6 O 0.4217(3) 0.56984(18) 0.11022(16) 0.0353(5) Uani 1 1 d .
O7 O 0.5180(2) 0.73863(17) 0.17119(15) 0.0288(5) Uani 1 1 d .
N1 N 0.3939(3) 0.4979(2) -0.2047(2) 0.0288(6) Uani 1 1 d .
N2 N 0.2025(3) 0.6749(2) -0.04076(18) 0.0249(5) Uani 1 1 d .
C1 C 0.4291(3) 0.7046(2) -0.1672(2) 0.0235(6) Uani 1 1 d .
C2 C 0.4904(3) 0.6012(3) -0.1920(2) 0.0260(6) Uani 1 1 d .
C3 C 0.6438(4) 0.5903(3) -0.2071(2) 0.0347(7) Uani 1 1 d .
H3 H 0.6831 0.5203 -0.2236 0.046 Uiso 1 1 calc R
C4 C 0.7390(4) 0.6842(3) -0.1975(3) 0.0410(9) Uani 1 1 d .
H4 H 0.8441 0.6779 -0.2070 0.055 Uiso 1 1 calc R
C5 C 0.6804(4) 0.7877(3) -0.1739(2) 0.0400(8) Uani 1 1 d .
H5 H 0.7460 0.8510 -0.1679 0.053 Uiso 1 1 calc R
C6 C 0.5258(4) 0.7985(3) -0.1593(2) 0.0314(7) Uani 1 1 d .
H6 H 0.4864 0.8689 -0.1441 0.042 Uiso 1 1 calc R
C7 C 0.2676(3) 0.7357(2) 0.0589(2) 0.0226(6) Uani 1 1 d .
H7 H 0.3024 0.8110 0.0402 0.030 Uiso 1 1 calc R
C8 C 0.1342(3) 0.7489(2) 0.1259(2) 0.0249(7) Uani 1 1 d .
C9 C 0.1210(3) 0.8099(2) 0.3063(2) 0.0248(6) Uani 1 1 d .
C10 C 0.1175(4) 0.7222(3) 0.3787(2) 0.0326(7) Uani 1 1 d .
H10 H 0.1712 0.6548 0.3721 0.043 Uiso 1 1 calc R
C11 C 0.0319(4) 0.7376(3) 0.4612(2) 0.0387(8) Uani 1 1 d .
H11 H 0.0271 0.6789 0.5096 0.052 Uiso 1 1 calc R
C12 C -0.0459(4) 0.8366(3) 0.4738(2) 0.0353(8) Uani 1 1 d .
C13 C -0.0389(4) 0.9229(3) 0.3999(2) 0.0319(7) Uani 1 1 d .
H13 H -0.0919 0.9906 0.4066 0.042 Uiso 1 1 calc R
C14 C 0.0451(3) 0.9098(3) 0.3172(2) 0.0275(6) Uani 1 1 d .
H14 H 0.0501 0.9685 0.2688 0.037 Uiso 1 1 calc R
C15 C 0.4103(3) 0.6706(3) 0.1173(2) 0.0276(7) Uani 1 1 d .
C16 C 0.6601(3) 0.6842(3) 0.2309(2) 0.0332(7) Uani 1 1 d .
H16A H 0.7403 0.7414 0.2536 0.044 Uiso 1 1 calc R
H16B H 0.7022 0.6319 0.1837 0.044 Uiso 1 1 calc R
C17 C 0.6270(3) 0.6217(3) 0.3274(2) 0.0289(7) Uani 1 1 d .
C18 C 0.5436(4) 0.6721(3) 0.3993(3) 0.0443(9) Uani 1 1 d .
H18 H 0.5062 0.7457 0.3872 0.059 Uiso 1 1 calc R
C19 C 0.5157(5) 0.6141(4) 0.4882(3) 0.0561(10) Uani 1 1 d .
H19 H 0.4584 0.6484 0.5357 0.075 Uiso 1 1 calc R
C20 C 0.5718(4) 0.5055(4) 0.5080(3) 0.0497(9) Uani 1 1 d .
H20 H 0.5532 0.4663 0.5685 0.066 Uiso 1 1 calc R
C21 C 0.6550(4) 0.4566(3) 0.4374(3) 0.0463(9) Uani 1 1 d .
H21 H 0.6938 0.3834 0.4497 0.062 Uiso 1 1 calc R
C22 C 0.6819(4) 0.5142(3) 0.3486(2) 0.0368(8) Uani 1 1 d .
H22 H 0.7390 0.4794 0.3012 0.049 Uiso 1 1 calc R
C23 C 0.0055(4) 0.8264(3) 0.0685(2) 0.0325(7) Uani 1 1 d .
H23A H -0.0757 0.8355 0.1118 0.049 Uiso 1 1 calc R
H23B H -0.0399 0.7939 0.0004 0.049 Uiso 1 1 calc R
H23C H 0.0505 0.8988 0.0571 0.049 Uiso 1 1 calc R
C24 C 0.0693(4) 0.6374(3) 0.1431(2) 0.0297(7) Uani 1 1 d .
C25 C 0.0141(4) 0.5472(3) 0.1531(3) 0.0422(8) Uani 1 1 d .
H25 H -0.0293 0.4762 0.1610 0.056 Uiso 1 1 calc R
C26 C -0.1356(5) 0.8530(4) 0.5651(3) 0.0575(11) Uani 1 1 d .
H26A H -0.1764 0.7815 0.5841 0.086 Uiso 1 1 calc R
H26B H -0.2221 0.9044 0.5433 0.086 Uiso 1 1 calc R
H26C H -0.0657 0.8836 0.6261 0.086 Uiso 1 1 calc R
H2 H 0.2085 0.5894 -0.0387 0.040 Uiso 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 0.0033 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O3 S1 O4 120.04(13)
O3 S1 N2 106.77(12)
O4 S1 N2 107.01(13)
O3 S1 C1 106.46(13)
O4 S1 C1 107.84(13)
N2 S1 C1 108.27(12)
C9 O5 C8 116.2(2)
C15 O7 C16 116.2(2)
O1 N1 O2 124.0(3)
O1 N1 C2 118.5(2)
O2 N1 C2 117.5(2)
C7 N2 S1 120.56(19)
C6 C1 C2 118.8(3)
C6 C1 S1 118.4(2)
C2 C1 S1 122.6(2)
C3 C2 C1 121.7(3)
C3 C2 N1 116.2(3)
C1 C2 N1 122.1(2)
C2 C3 C4 118.8(3)
C3 C4 C5 120.5(3)
C6 C5 C4 120.5(3)
C5 C6 C1 119.7(3)
N2 C7 C15 108.7(2)
N2 C7 C8 108.1(2)
C15 C7 C8 113.2(2)
O5 C8 C24 111.5(2)
O5 C8 C23 111.2(2)
C24 C8 C23 110.7(2)
O5 C8 C7 104.0(2)
C24 C8 C7 109.1(2)
C23 C8 C7 110.2(2)
C14 C9 C10 121.1(3)
C14 C9 O5 119.7(2)
C10 C9 O5 119.1(3)
C11 C10 C9 118.1(3)
C12 C11 C10 122.1(3)
C11 C12 C13 118.2(3)
C11 C12 C26 121.5(3)
C13 C12 C26 120.3(3)
C14 C13 C12 120.9(3)
C9 C14 C13 119.6(3)
O6 C15 O7 125.8(3)
O6 C15 C7 122.3(3)
O7 C15 C7 111.8(3)
O7 C16 C17 112.3(2)
C22 C17 C18 118.2(3)
C22 C17 C16 120.9(3)
C18 C17 C16 120.9(3)
C19 C18 C17 120.2(4)
C18 C19 C20 120.7(4)
C21 C20 C19 118.8(3)
C20 C21 C22 120.5(4)
C21 C22 C17 121.6(3)
C25 C24 C8 177.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O3 1.423(2)
S1 O4 1.431(2)
S1 N2 1.613(2)
S1 C1 1.761(3)
O1 N1 1.214(3)
O2 N1 1.220(3)
O5 C9 1.394(3)
O5 C8 1.443(3)
O6 C15 1.200(4)
O7 C15 1.319(4)
O7 C16 1.463(4)
N1 C2 1.467(4)
N2 C7 1.471(4)
C1 C6 1.377(4)
C1 C2 1.387(4)
C2 C3 1.364(4)
C3 C4 1.369(5)
C4 C5 1.374(5)
C5 C6 1.372(4)
C7 C15 1.521(4)
C7 C8 1.540(4)
C8 C24 1.460(4)
C8 C23 1.516(4)
C9 C14 1.366(4)
C9 C10 1.385(4)
C10 C11 1.383(4)
C11 C12 1.368(5)
C12 C13 1.390(5)
C12 C26 1.502(4)
C13 C14 1.374(4)
C16 C17 1.492(4)
C17 C22 1.365(5)
C17 C18 1.381(4)
C18 C19 1.370(5)
C19 C20 1.379(6)
C20 C21 1.361(5)
C21 C22 1.364(4)
C24 C25 1.182(5)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2 O1 1.01 2.18 2.940(3) 130.8
