#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/43/7204398.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_7204398
loop_
_publ_author_name
'Yolanda S. P. Álvares'
'M. José Alves'
'Nuno G. Azoia'
'Jamie F. Bickley'
'Thomas L. Gilchrist'
_publ_section_title
;
 Diastereoselective synthesis of aziridines from
 (1R)-10-(N,N-dialkylsulfamoyl)isobornyl 2H-azirine-3-carboxylates
;
_journal_issue                   16
_journal_name_full               'J. Chem. Soc., Perkin Trans. 1'
_journal_page_first              1911
_journal_page_last               1919
_journal_paper_doi               10.1039/b202321k
_journal_year                    2002
_chemical_formula_sum            'C22 H33 N3 O5 S'
_chemical_formula_weight         451.57
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.807(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.0165(15)
_cell_length_b                   12.3521(15)
_cell_length_c                   10.5145(16)
_cell_measurement_temperature    213(2)
_cell_volume                     1171.2(3)
_computing_data_collection       'IPDS (STOE, 1997)'
_computing_data_reduction        'X-RED (STOE, 1996)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      213(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       'Image plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_sigmaI/netI    0.0626
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7463
_diffrn_reflns_theta_full        24.24
_diffrn_reflns_theta_max         24.24
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  0.9493
_exptl_absorpt_correction_T_min  0.9021
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3673
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.915
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0370
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0429P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0871
_reflns_number_gt                2856
_reflns_number_total             3673
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b202321k.txt
_cod_data_source_block           za155
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7204398
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1937(3) 1.1295(2) 0.2915(3) 0.0499(8) Uani 1 1 d . . .
H1A H 0.1575 1.1611 0.1969 0.060 Uiso 1 1 calc R . .
H1B H 0.1167 1.0986 0.3144 0.060 Uiso 1 1 calc R . .
C2 C 0.3404(3) 1.0764(2) 0.3511(3) 0.0363(6) Uani 1 1 d . . .
C3 C 0.4620(3) 0.9919(3) 0.5879(3) 0.0512(7) Uani 1 1 d . . .
H3 H 0.5195 1.0520 0.6358 0.061 Uiso 1 1 calc R . .
C4 C 0.4598(4) 0.8944(3) 0.6471(4) 0.0657(10) Uani 1 1 d . . .
H4 H 0.5150 0.8751 0.7424 0.079 Uiso 1 1 calc R . .
C5 C 0.3618(4) 0.8290(3) 0.5417(4) 0.0607(9) Uani 1 1 d . . .
H5 H 0.3378 0.7571 0.5526 0.073 Uiso 1 1 calc R . .
C6 C 0.3052(3) 0.8868(2) 0.4179(3) 0.0452(7) Uani 1 1 d . . .
C7 C 0.2085(4) 0.8487(3) 0.2808(5) 0.0649(10) Uani 1 1 d . . .
H7 H 0.1701 0.7786 0.2761 0.078 Uiso 1 1 calc R . .
C8 C 0.4255(3) 1.0769(2) 0.2639(3) 0.0339(6) Uani 1 1 d . . .
C9 C 0.6035(3) 0.9888(2) 0.2099(2) 0.0327(6) Uani 1 1 d . . .
H9 H 0.6487 1.0607 0.2136 0.039 Uiso 1 1 calc R . .
C10 C 0.5146(3) 0.9519(2) 0.0554(3) 0.0443(7) Uani 1 1 d . . .
H10A H 0.4117 0.9352 0.0355 0.053 Uiso 1 1 calc R . .
H10B H 0.5151 1.0077 -0.0105 0.053 Uiso 1 1 calc R . .
C11 C 0.5957(3) 0.8509(2) 0.0448(3) 0.0461(7) Uani 1 1 d . . .
H11 H 0.5364 0.8034 -0.0360 0.055 Uiso 1 1 calc R . .
C12 C 0.7434(4) 0.8876(3) 0.0486(3) 0.0654(10) Uani 1 1 d . . .
H12A H 0.7288 0.9462 -0.0190 0.078 Uiso 1 1 calc R . .
H12B H 0.7949 0.8274 0.0283 0.078 Uiso 1 1 calc R . .
C13 C 0.8298(3) 0.9276(3) 0.2030(3) 0.0552(9) Uani 1 1 d . . .
H13A H 0.8500 1.0055 0.2059 0.066 Uiso 1 1 calc R . .
H13B H 0.9239 0.8887 0.2514 0.066 Uiso 1 1 calc R . .
C14 C 0.7232(3) 0.9021(2) 0.2714(3) 0.0340(6) Uani 1 1 d . . .
C15 C 0.6435(3) 0.7973(2) 0.1903(3) 0.0397(7) Uani 1 1 d . . .
C16 C 0.7484(4) 0.7010(3) 0.2179(4) 0.0677(10) Uani 1 1 d . . .
H16A H 0.6930 0.6387 0.1649 0.081 Uiso 1 1 calc R . .
H16B H 0.7940 0.6840 0.3179 0.081 Uiso 1 1 calc R . .
H16C H 0.8249 0.7191 0.1883 0.081 Uiso 1 1 calc R . .
C17 C 0.5130(4) 0.7578(2) 0.2159(3) 0.0469(7) Uani 1 1 d . . .
H17A H 0.4716 0.6930 0.1607 0.056 Uiso 1 1 calc R . .
H17B H 0.4376 0.8137 0.1880 0.056 Uiso 1 1 calc R . .
H17C H 0.5467 0.7416 0.3154 0.056 Uiso 1 1 calc R . .
C18 C 0.7988(3) 0.8902(2) 0.4321(3) 0.0374(6) Uani 1 1 d . . .
H18A H 0.8671 0.8286 0.4558 0.045 Uiso 1 1 calc R . .
H18B H 0.7226 0.8720 0.4635 0.045 Uiso 1 1 calc R . .
C19 C 0.9077(4) 0.9652(3) 0.7852(4) 0.0719(11) Uani 1 1 d . . .
H19A H 0.9241 0.8961 0.8355 0.086 Uiso 1 1 calc R . .
H19B H 0.8007 0.9738 0.7278 0.086 Uiso 1 1 calc R . .
C20 C 0.9638(6) 1.0562(4) 0.8910(4) 0.0901(14) Uani 1 1 d . . .
H20A H 0.9137 1.0542 0.9518 0.108 Uiso 1 1 calc R . .
H20B H 0.9441 1.1250 0.8415 0.108 Uiso 1 1 calc R . .
H20C H 1.0697 1.0481 0.9477 0.108 Uiso 1 1 calc R . .
C21 C 1.1312(3) 0.9150(3) 0.7450(4) 0.0672(10) Uani 1 1 d . . .
H21A H 1.1941 0.9484 0.8362 0.081 Uiso 1 1 calc R . .
H21B H 1.1739 0.9328 0.6796 0.081 Uiso 1 1 calc R . .
C22 C 1.1361(5) 0.7953(3) 0.7639(5) 0.0949(14) Uani 1 1 d . . .
H22A H 1.2380 0.7705 0.8007 0.114 Uiso 1 1 calc R . .
H22B H 1.0778 0.7609 0.6735 0.114 Uiso 1 1 calc R . .
H22C H 1.0956 0.7764 0.8296 0.114 Uiso 1 1 calc R . .
N1 N 0.3221(3) 1.1808(2) 0.4064(3) 0.0485(7) Uani 1 1 d . . .
H1 H 0.362(4) 1.231(3) 0.378(3) 0.059(11) Uiso 1 1 d . . .
N2 N 0.3676(2) 0.98803(18) 0.4485(2) 0.0363(5) Uani 1 1 d . . .
N3 N 0.9832(3) 0.9632(2) 0.6915(2) 0.0551(7) Uani 1 1 d . . .
O1 O 0.1698(2) 0.8956(2) 0.1694(3) 0.0717(7) Uani 1 1 d . . .
O2 O 0.4151(3) 1.14953(16) 0.1844(2) 0.0549(6) Uani 1 1 d . . .
O3 O 0.51155(17) 0.99048(14) 0.28654(15) 0.0307(4) Uani 1 1 d . . .
O4 O 0.7920(3) 1.0831(2) 0.5236(3) 0.0878(8) Uani 1 1 d . . .
O5 O 1.0104(3) 1.0306(2) 0.4852(2) 0.0815(9) Uani 1 1 d . . .
S1 S 0.89898(8) 1.00355(6) 0.53072(7) 0.0511(2) Uani 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 59.33(18) . . ?
N2 C2 N1 113.8(2) . . ?
N2 C2 C1 118.9(2) . . ?
N1 C2 C1 60.11(19) . . ?
N2 C2 C8 117.2(2) . . ?
N1 C2 C8 116.3(2) . . ?
C1 C2 C8 117.7(2) . . ?
N2 C3 C4 108.7(3) . . ?
C3 C4 C5 107.4(3) . . ?
C6 C5 C4 108.3(3) . . ?
C5 C6 N2 107.1(3) . . ?
C5 C6 C7 127.4(3) . . ?
N2 C6 C7 125.4(3) . . ?
O1 C7 C6 127.8(3) . . ?
O2 C8 O3 125.4(2) . . ?
O2 C8 C2 122.0(2) . . ?
O3 C8 C2 112.6(2) . . ?
O3 C9 C14 110.05(19) . . ?
O3 C9 C10 111.73(19) . . ?
C14 C9 C10 103.1(2) . . ?
C11 C10 C9 103.8(2) . . ?
C10 C11 C12 107.2(3) . . ?
C10 C11 C15 103.0(2) . . ?
C12 C11 C15 102.9(2) . . ?
C11 C12 C13 102.4(2) . . ?
C12 C13 C14 103.7(2) . . ?
C9 C14 C18 117.1(2) . . ?
C9 C14 C13 103.4(2) . . ?
C18 C14 C13 114.9(2) . . ?
C9 C14 C15 103.3(2) . . ?
C18 C14 C15 114.4(2) . . ?
C13 C14 C15 101.9(2) . . ?
C17 C15 C16 106.8(3) . . ?
C17 C15 C11 113.1(2) . . ?
C16 C15 C11 114.5(2) . . ?
C17 C15 C14 116.2(2) . . ?
C16 C15 C14 113.3(2) . . ?
C11 C15 C14 92.9(2) . . ?
C14 C18 S1 116.92(19) . . ?
N3 C19 C20 111.7(3) . . ?
N3 C21 C22 115.1(3) . . ?
C2 N1 C1 60.56(18) . . ?
C3 N2 C6 108.5(2) . . ?
C3 N2 C2 124.7(2) . . ?
C6 N2 C2 126.8(2) . . ?
C21 N3 C19 118.4(3) . . ?
C21 N3 S1 120.8(2) . . ?
C19 N3 S1 120.6(2) . . ?
C8 O3 C9 115.34(19) . . ?
O4 S1 O5 119.78(19) . . ?
O4 S1 N3 107.88(15) . . ?
O5 S1 N3 107.17(13) . . ?
O4 S1 C18 106.97(14) . . ?
O5 S1 C18 108.31(13) . . ?
N3 S1 C18 105.96(14) . . ?
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
C1 N1 1.471(4) . ?
C1 C2 1.477(4) . ?
C2 N2 1.439(3) . ?
C2 N1 1.459(3) . ?
C2 C8 1.498(3) . ?
C3 N2 1.356(3) . ?
C3 C4 1.360(4) . ?
C4 C5 1.378(5) . ?
C5 C6 1.372(4) . ?
C6 N2 1.372(4) . ?
C6 C7 1.422(5) . ?
C7 O1 1.210(4) . ?
C8 O2 1.199(3) . ?
C8 O3 1.327(3) . ?
C9 O3 1.465(3) . ?
C9 C14 1.526(4) . ?
C9 C10 1.542(3) . ?
C10 C11 1.519(4) . ?
C11 C12 1.531(4) . ?
C11 C15 1.539(4) . ?
C12 C13 1.551(4) . ?
C13 C14 1.557(4) . ?
C14 C18 1.528(3) . ?
C14 C15 1.564(4) . ?
C15 C17 1.526(4) . ?
C15 C16 1.529(4) . ?
C18 S1 1.771(3) . ?
C19 N3 1.481(4) . ?
C19 C20 1.508(5) . ?
C21 N3 1.463(4) . ?
C21 C22 1.491(5) . ?
N3 S1 1.605(2) . ?
O4 S1 1.432(3) . ?
O5 S1 1.432(2) . ?
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
N1 C1 C2 N2 102.4(3) . . . . ?
N1 C1 C2 C8 -106.1(3) . . . . ?
N2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 N2 -0.7(3) . . . . ?
C4 C5 C6 C7 175.1(3) . . . . ?
C5 C6 C7 O1 -172.0(3) . . . . ?
N2 C6 C7 O1 3.1(5) . . . . ?
N2 C2 C8 O2 -176.7(3) . . . . ?
N1 C2 C8 O2 -37.2(4) . . . . ?
C1 C2 C8 O2 31.2(4) . . . . ?
N2 C2 C8 O3 2.6(3) . . . . ?
N1 C2 C8 O3 142.2(2) . . . . ?
C1 C2 C8 O3 -149.4(2) . . . . ?
O3 C9 C10 C11 -119.8(2) . . . . ?
C14 C9 C10 C11 -1.7(2) . . . . ?
C9 C10 C11 C12 -71.5(3) . . . . ?
C9 C10 C11 C15 36.6(3) . . . . ?
C10 C11 C12 C13 69.3(3) . . . . ?
C15 C11 C12 C13 -38.9(3) . . . . ?
C11 C12 C13 C14 3.3(3) . . . . ?
O3 C9 C14 C18 -40.5(3) . . . . ?
C10 C9 C14 C18 -159.8(2) . . . . ?
O3 C9 C14 C13 -167.9(2) . . . . ?
C10 C9 C14 C13 72.8(2) . . . . ?
O3 C9 C14 C15 86.2(2) . . . . ?
C10 C9 C14 C15 -33.1(2) . . . . ?
C12 C13 C14 C9 -74.5(3) . . . . ?
C12 C13 C14 C18 156.6(3) . . . . ?
C12 C13 C14 C15 32.4(3) . . . . ?
C10 C11 C15 C17 65.9(3) . . . . ?
C12 C11 C15 C17 177.3(2) . . . . ?
C10 C11 C15 C16 -171.5(3) . . . . ?
C12 C11 C15 C16 -60.1(3) . . . . ?
C10 C11 C15 C14 -54.2(2) . . . . ?
C12 C11 C15 C14 57.1(3) . . . . ?
C9 C14 C15 C17 -64.4(3) . . . . ?
C18 C14 C15 C17 64.0(3) . . . . ?
C13 C14 C15 C17 -171.4(2) . . . . ?
C9 C14 C15 C16 171.4(2) . . . . ?
C18 C14 C15 C16 -60.2(3) . . . . ?
C13 C14 C15 C16 64.4(3) . . . . ?
C9 C14 C15 C11 53.2(2) . . . . ?
C18 C14 C15 C11 -178.4(2) . . . . ?
C13 C14 C15 C11 -53.8(2) . . . . ?
C9 C14 C18 S1 -62.0(3) . . . . ?
C13 C14 C18 S1 59.7(3) . . . . ?
C15 C14 C18 S1 177.01(18) . . . . ?
N2 C2 N1 C1 -110.8(3) . . . . ?
C8 C2 N1 C1 108.3(3) . . . . ?
C4 C3 N2 C6 -0.5(3) . . . . ?
C4 C3 N2 C2 180.0(2) . . . . ?
C5 C6 N2 C3 0.7(3) . . . . ?
C7 C6 N2 C3 -175.2(3) . . . . ?
C5 C6 N2 C2 -179.8(2) . . . . ?
C7 C6 N2 C2 4.4(4) . . . . ?
N1 C2 N2 C3 -43.8(3) . . . . ?
C1 C2 N2 C3 -111.6(3) . . . . ?
C8 C2 N2 C3 96.8(3) . . . . ?
N1 C2 N2 C6 136.7(3) . . . . ?
C1 C2 N2 C6 69.0(3) . . . . ?
C8 C2 N2 C6 -82.7(3) . . . . ?
C22 C21 N3 C19 69.6(4) . . . . ?
C22 C21 N3 S1 -105.2(4) . . . . ?
C20 C19 N3 C21 79.7(4) . . . . ?
C20 C19 N3 S1 -105.5(3) . . . . ?
O2 C8 O3 C9 2.3(4) . . . . ?
C2 C8 O3 C9 -177.00(19) . . . . ?
C14 C9 O3 C8 165.8(2) . . . . ?
C10 C9 O3 C8 -80.3(3) . . . . ?
C21 N3 S1 O4 -156.8(3) . . . . ?
C19 N3 S1 O4 28.5(3) . . . . ?
C21 N3 S1 O5 -26.6(3) . . . . ?
C19 N3 S1 O5 158.7(3) . . . . ?
C21 N3 S1 C18 88.9(3) . . . . ?
C19 N3 S1 C18 -85.8(3) . . . . ?
C14 C18 S1 O4 72.6(2) . . . . ?
C14 C18 S1 O5 -57.8(2) . . . . ?
C14 C18 S1 N3 -172.52(19) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9191030
