#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:01:04 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178416 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/37/4023722.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_4023722
loop_
_publ_author_name
'Susannah C. Coote'
'Stephen P. Moore'
'Peter O'Brien'
'Adrian C. Whitwood'
'John Gilday'
_publ_section_title
;
 Organolithium-Mediated Conversion of β-Alkoxy Aziridines into
 Allylic Sulfonamides: Effect of the N-Sulfonyl Group and a Formal
 Synthesis of (\+-)-Perhydrohistrionicotoxin
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7852
_journal_page_last               7855
_journal_paper_doi               10.1021/jo801586h
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C12 H23 N O3 S'
_chemical_formula_sum            'C12 H23 N O3 S'
_chemical_formula_weight         261.37
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 93.247(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7745(9)
_cell_length_b                   12.6882(12)
_cell_length_c                   10.8430(10)
_cell_measurement_reflns_used    2791
_cell_measurement_temperature    383(2)
_cell_measurement_theta_max      29.88
_cell_measurement_theta_min      2.47
_cell_volume                     1342.6(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      383(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10463
_diffrn_reflns_theta_full        30.02
_diffrn_reflns_theta_max         30.02
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.03;(Sheldrick)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3868
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0423
_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)+(0.0473P)²+0.4336P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1033
_reflns_number_gt                3152
_reflns_number_total             3868
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801586h_si_001.cif
_cod_data_source_block           pob0606m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023722
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C1 C 0.61509(14) 0.91068(11) 0.13295(12) 0.0148(3) Uani 1 1 d . . .
C2 C 0.65439(14) 0.81939(11) 0.08560(13) 0.0165(3) Uani 1 1 d . . .
C3 C 0.80400(15) 0.79097(11) 0.07834(14) 0.0198(3) Uani 1 1 d . . .
H3A H 0.8193 0.7692 -0.0055 0.024 Uiso 1 1 calc R . .
H3B H 0.8239 0.7310 0.1319 0.024 Uiso 1 1 calc R . .
C4 C 0.90456(15) 0.87932(12) 0.11433(14) 0.0209(3) Uani 1 1 d . . .
H4A H 0.9930 0.8492 0.1395 0.025 Uiso 1 1 calc R . .
H4B H 0.9164 0.9243 0.0434 0.025 Uiso 1 1 calc R . .
C5 C 0.85248(14) 0.94465(12) 0.21954(14) 0.0193(3) Uani 1 1 d . . .
H5A H 0.9179 0.9999 0.2418 0.023 Uiso 1 1 calc R . .
H5B H 0.8429 0.9002 0.2913 0.023 Uiso 1 1 calc R . .
C6 C 0.71452(14) 0.99341(11) 0.18011(13) 0.0153(3) Uani 1 1 d . . .
H6 H 0.6774 1.0291 0.2511 0.018 Uiso 1 1 calc R . .
C7 C 0.55606(16) 0.73590(12) 0.03808(15) 0.0241(3) Uani 1 1 d . . .
H7A H 0.4647 0.7547 0.0579 0.036 Uiso 1 1 calc R . .
H7B H 0.5804 0.6696 0.0759 0.036 Uiso 1 1 calc R . .
H7C H 0.5602 0.7301 -0.0499 0.036 Uiso 1 1 calc R . .
C8 C 0.80026(17) 1.16074(12) 0.10961(15) 0.0245(3) Uani 1 1 d . . .
H8A H 0.7660 1.1929 0.1818 0.037 Uiso 1 1 calc R . .
H8B H 0.7915 1.2092 0.0417 0.037 Uiso 1 1 calc R . .
H8C H 0.8950 1.1426 0.1254 0.037 Uiso 1 1 calc R . .
C9 C 0.31307(14) 1.03419(10) 0.30479(12) 0.0142(3) Uani 1 1 d . . .
C10 C 0.42173(15) 1.11873(11) 0.32970(14) 0.0195(3) Uani 1 1 d . . .
H10A H 0.4725 1.1285 0.2573 0.029 Uiso 1 1 calc R . .
H10B H 0.4829 1.0972 0.3974 0.029 Uiso 1 1 calc R . .
H10C H 0.3783 1.1838 0.3500 0.029 Uiso 1 1 calc R . .
C11 C 0.23728(16) 1.01135(13) 0.42136(14) 0.0232(3) Uani 1 1 d . . .
H11A H 0.3016 0.9881 0.4859 0.035 Uiso 1 1 calc R . .
H11B H 0.1702 0.9573 0.4042 0.035 Uiso 1 1 calc R . .
H11C H 0.1926 1.0743 0.4472 0.035 Uiso 1 1 calc R . .
C12 C 0.21381(14) 1.06619(11) 0.19817(14) 0.0180(3) Uani 1 1 d . . .
H12A H 0.1665 1.1293 0.2197 0.027 Uiso 1 1 calc R . .
H12B H 0.1486 1.0107 0.1817 0.027 Uiso 1 1 calc R . .
H12C H 0.2637 1.0788 0.1259 0.027 Uiso 1 1 calc R . .
N1 N 0.47268(12) 0.94001(9) 0.13732(11) 0.0147(2) Uani 1 1 d . . .
H1 H 0.4213(19) 0.9298(14) 0.0732(18) 0.024(5) Uiso 1 1 d . . .
O1 O 0.28695(11) 0.83725(8) 0.23472(11) 0.0242(2) Uani 1 1 d . . .
O2 O 0.49835(11) 0.88575(9) 0.35694(10) 0.0221(2) Uani 1 1 d . . .
O3 O 0.72354(10) 1.06800(8) 0.07985(9) 0.0175(2) Uani 1 1 d . . .
S1 S 0.39421(3) 0.91228(3) 0.26334(3) 0.01444(10) 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
C2 C1 N1 122.42(13) . . ?
C2 C1 C6 122.96(12) . . ?
N1 C1 C6 114.55(11) . . ?
C1 C2 C7 123.54(13) . . ?
C1 C2 C3 121.87(13) . . ?
C7 C2 C3 114.57(12) . . ?
C2 C3 C4 114.96(12) . . ?
C2 C3 H3A 108.5 . . ?
C4 C3 H3A 108.5 . . ?
C2 C3 H3B 108.5 . . ?
C4 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C5 C4 C3 110.73(12) . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C4 C5 C6 109.85(12) . . ?
C4 C5 H5A 109.7 . . ?
C6 C5 H5A 109.7 . . ?
C4 C5 H5B 109.7 . . ?
C6 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
O3 C6 C1 105.50(11) . . ?
O3 C6 C5 112.69(11) . . ?
C1 C6 C5 110.96(12) . . ?
O3 C6 H6 109.2 . . ?
C1 C6 H6 109.2 . . ?
C5 C6 H6 109.2 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O3 C8 H8A 109.5 . . ?
O3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C12 C9 C10 110.80(11) . . ?
C12 C9 C11 111.15(12) . . ?
C10 C9 C11 110.65(12) . . ?
C12 C9 S1 108.03(9) . . ?
C10 C9 S1 109.61(10) . . ?
C11 C9 S1 106.47(9) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 N1 S1 117.93(9) . . ?
C1 N1 H1 117.6(13) . . ?
S1 N1 H1 111.6(13) . . ?
C8 O3 C6 115.10(11) . . ?
O2 S1 O1 118.46(7) . . ?
O2 S1 N1 107.01(6) . . ?
O1 S1 N1 109.37(7) . . ?
O2 S1 C9 109.17(7) . . ?
O1 S1 C9 107.20(6) . . ?
N1 S1 C9 104.82(6) . . ?
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 C2 1.3324(19) . ?
C1 N1 1.4442(17) . ?
C1 C6 1.5006(19) . ?
C2 C7 1.502(2) . ?
C2 C3 1.513(2) . ?
C3 C4 1.527(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.521(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.5228(19) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 O3 1.4477(17) . ?
C6 H6 0.9800 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 O3 1.4226(17) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C12 1.5217(19) . ?
C9 C10 1.5229(19) . ?
C9 C11 1.5285(19) . ?
C9 S1 1.8067(14) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N1 S1 1.6425(12) . ?
N1 H1 0.84(2) . ?
O1 S1 1.4370(11) . ?
O2 S1 1.4361(11) . ?
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
_geom_hbond_site_symmetry_A
N1 H1 O3 0.84(2) 2.12(2) 2.9534(16) 169.3(17) 3_675
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 C7 -3.1(2) . . . . ?
C6 C1 C2 C7 180.00(13) . . . . ?
N1 C1 C2 C3 178.25(12) . . . . ?
C6 C1 C2 C3 1.4(2) . . . . ?
C1 C2 C3 C4 -7.1(2) . . . . ?
C7 C2 C3 C4 174.18(13) . . . . ?
C2 C3 C4 C5 36.24(17) . . . . ?
C3 C4 C5 C6 -59.94(16) . . . . ?
C2 C1 C6 O3 97.28(15) . . . . ?
N1 C1 C6 O3 -79.81(13) . . . . ?
C2 C1 C6 C5 -25.06(18) . . . . ?
N1 C1 C6 C5 157.85(11) . . . . ?
C4 C5 C6 O3 -64.39(15) . . . . ?
C4 C5 C6 C1 53.66(16) . . . . ?
C2 C1 N1 S1 93.20(15) . . . . ?
C6 C1 N1 S1 -89.70(13) . . . . ?
C1 C6 O3 C8 172.67(11) . . . . ?
C5 C6 O3 C8 -66.12(15) . . . . ?
C1 N1 S1 O2 13.92(12) . . . . ?
C1 N1 S1 O1 -115.56(11) . . . . ?
C1 N1 S1 C9 129.78(10) . . . . ?
C12 C9 S1 O2 174.27(9) . . . . ?
C10 C9 S1 O2 53.46(11) . . . . ?
C11 C9 S1 O2 -66.26(11) . . . . ?
C12 C9 S1 O1 -56.25(11) . . . . ?
C10 C9 S1 O1 -177.06(10) . . . . ?
C11 C9 S1 O1 63.22(11) . . . . ?
C12 C9 S1 N1 59.93(10) . . . . ?
C10 C9 S1 N1 -60.89(11) . . . . ?
C11 C9 S1 N1 179.39(9) . . . . ?
