#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:34:33 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178473 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/94/4029467.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_4029467
loop_
_publ_author_name
'Kelley, Brandon T.'
'Carroll, Patrick'
'Joullié, Madeleine M'
_publ_section_title
;
 Possible Reason for the Unusual Regioselectivity in Nucleophilic Ring
 Opening of Trisubstituted Aziridines under Mildly Basic Conditions.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5121
_journal_page_last               5133
_journal_paper_doi               10.1021/jo5006685
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C11 H15 N O2 S'
_chemical_formula_weight         225.30
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.5620(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4009(5)
_cell_length_b                   7.2781(3)
_cell_length_c                   12.4672(5)
_cell_measurement_temperature    143(1)
_cell_volume                     1121.66(8)
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0155
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10508
_diffrn_reflns_theta_full        25.14
_diffrn_reflns_theta_max         25.14
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6339
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1992
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0453P)²+0.6711P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0897
_reflns_number_gt                1842
_reflns_number_total             1992
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5006685_si_006.cif
_cod_data_source_block           shelxl
_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 

 Adding full bibliography for 4029464--4029472.cif.
;
_cod_original_sg_symbol_H-M      'P 21     '
_cod_database_code               4029467
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
C1 C 0.64432(12) 0.1865(2) 0.34599(12) 0.0224(3) Uani 1 1 d .
C2 C 0.71043(13) 0.2509(2) 0.26999(12) 0.0263(3) Uani 1 1 d .
H2 H 0.6811 0.2855 0.2020 0.035 Uiso 1 1 calc R
C3 C 0.82094(13) 0.2632(2) 0.29634(13) 0.0273(4) Uani 1 1 d .
H3 H 0.8658 0.3046 0.2451 0.036 Uiso 1 1 calc R
C4 C 0.86564(12) 0.2145(2) 0.39820(13) 0.0256(3) Uani 1 1 d .
C5 C 0.79710(13) 0.1496(2) 0.47300(13) 0.0266(4) Uani 1 1 d .
H5 H 0.8262 0.1162 0.5413 0.035 Uiso 1 1 calc R
C6 C 0.68666(12) 0.1338(2) 0.44809(12) 0.0250(3) Uani 1 1 d .
H6 H 0.6418 0.0890 0.4984 0.033 Uiso 1 1 calc R
C7 C 0.98571(13) 0.2335(3) 0.42651(15) 0.0369(4) Uani 1 1 d .
H7A H 1.0214 0.1215 0.4093 0.055 Uiso 1 1 calc R
H7B H 0.9988 0.2583 0.5021 0.055 Uiso 1 1 calc R
H7C H 1.0133 0.3329 0.3861 0.055 Uiso 1 1 calc R
C8 C 0.33823(12) 0.3632(2) 0.38877(13) 0.0267(4) Uani 1 1 d .
C9 C 0.42041(13) 0.4972(2) 0.35704(15) 0.0308(4) Uani 1 1 d .
H9A H 0.4363 0.6017 0.4039 0.041 Uiso 1 1 calc R
H9B H 0.4234 0.5224 0.2809 0.041 Uiso 1 1 calc R
C10 C 0.29475(14) 0.3785(2) 0.49769(14) 0.0342(4) Uani 1 1 d .
H10A H 0.3482 0.4347 0.5472 0.051 Uiso 1 1 calc R
H10B H 0.2779 0.2582 0.5231 0.051 Uiso 1 1 calc R
H10C H 0.2304 0.4525 0.4923 0.051 Uiso 1 1 calc R
C11 C 0.26108(13) 0.2756(3) 0.30391(14) 0.0334(4) Uani 1 1 d .
H11A H 0.1961 0.3476 0.2945 0.050 Uiso 1 1 calc R
H11B H 0.2436 0.1536 0.3261 0.050 Uiso 1 1 calc R
H11C H 0.2944 0.2699 0.2371 0.050 Uiso 1 1 calc R
N1 N 0.45640(10) 0.31278(18) 0.39703(10) 0.0239(3) Uani 1 1 d .
O1 O 0.46838(9) -0.01283(16) 0.34346(10) 0.0333(3) Uani 1 1 d .
O2 O 0.48334(9) 0.2186(2) 0.20104(9) 0.0385(3) Uani 1 1 d .
S1 S 0.50417(3) 0.16538(5) 0.31206(3) 0.02465(15) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0206(7) 0.0225(7) 0.0243(8) -0.0022(6) 0.0032(6) 0.0013(6)
C2 0.0281(8) 0.0287(8) 0.0222(7) 0.0021(6) 0.0030(6) 0.0004(6)
C3 0.0269(8) 0.0286(8) 0.0276(8) 0.0020(6) 0.0091(6) -0.0020(6)
C4 0.0228(8) 0.0242(7) 0.0300(8) -0.0013(6) 0.0039(6) 0.0019(6)
C5 0.0256(8) 0.0302(8) 0.0241(8) 0.0039(6) 0.0018(6) 0.0054(6)
C6 0.0239(8) 0.0264(8) 0.0254(8) 0.0024(6) 0.0070(6) 0.0012(6)
C7 0.0230(8) 0.0511(11) 0.0369(9) 0.0039(8) 0.0039(7) -0.0007(8)
C8 0.0198(7) 0.0253(8) 0.0346(9) 0.0009(6) 0.0005(6) 0.0039(6)
C9 0.0234(8) 0.0274(8) 0.0412(9) 0.0039(7) 0.0002(7) 0.0025(6)
C10 0.0296(8) 0.0322(9) 0.0420(10) -0.0072(7) 0.0097(7) 0.0022(7)
C11 0.0212(8) 0.0403(9) 0.0379(9) 0.0013(8) -0.0023(7) -0.0015(7)
N1 0.0193(6) 0.0274(7) 0.0247(7) -0.0019(5) 0.0009(5) 0.0020(5)
O1 0.0259(6) 0.0313(6) 0.0434(7) -0.0088(5) 0.0072(5) -0.0040(5)
O2 0.0292(6) 0.0643(9) 0.0216(6) -0.0030(6) -0.0004(5) 0.0003(6)
S1 0.0201(2) 0.0315(2) 0.0223(2) -0.00436(14) 0.00165(15) -0.00042(14)
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
C2 C1 C6 121.26(14)
C2 C1 S1 119.48(12)
C6 C1 S1 119.25(11)
C1 C2 C3 119.22(14)
C2 C3 C4 120.97(14)
C3 C4 C5 118.53(14)
C3 C4 C7 120.29(14)
C5 C4 C7 121.18(15)
C6 C5 C4 121.54(14)
C5 C6 C1 118.47(14)
C9 C8 C10 119.61(15)
C9 C8 N1 59.62(10)
C10 C8 N1 111.89(13)
C9 C8 C11 120.01(15)
C10 C8 C11 114.27(14)
N1 C8 C11 120.24(13)
C8 C9 N1 60.85(10)
C9 N1 C8 59.53(10)
C9 N1 S1 118.99(11)
C8 N1 S1 120.77(10)
O1 S1 O2 117.98(8)
O1 S1 N1 106.12(7)
O2 S1 N1 113.32(8)
O1 S1 C1 109.51(7)
O2 S1 C1 107.77(7)
N1 S1 C1 100.76(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.383(2)
C1 C6 1.392(2)
C1 S1 1.7624(15)
C2 C3 1.387(2)
C3 C4 1.391(2)
C4 C5 1.393(2)
C4 C7 1.509(2)
C5 C6 1.385(2)
C8 C9 1.487(2)
C8 C10 1.505(2)
C8 N1 1.5063(19)
C8 C11 1.510(2)
C9 N1 1.488(2)
N1 S1 1.6504(13)
O1 S1 1.4353(12)
O2 S1 1.4407(12)
