#------------------------------------------------------------------------------
#$Date: 2017-10-13 01:32:00 +0200 (vie 13 de oct de 2017) $
#$Revision: 201954 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/65/1506512.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_1506512
loop_
_publ_author_name
'Fernández, Inmaculada'
'Valdivia, Victoria'
'Gori, Beatrice'
'Alcudia, Felipe'
'Alvarez, Eleuterio'
'Khiar, Noureddine'
_publ_section_title
;
 The isopropylsulfinyl group: a useful chiral controller for the
 asymmetric aziridination of sulfinylimines and the organocatalytic
 allylation of hydrazones.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1307
_journal_page_last               1310
_journal_paper_doi               10.1021/ol050080h
_journal_volume                  7
_journal_year                    2005
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H13 N O S'
_chemical_formula_sum            'C10 H13 N O S'
_chemical_formula_weight         195.27
_chemical_name_systematic
;
  ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.9008(2)
_cell_length_b                   9.6079(3)
_cell_length_c                   17.7589(6)
_cell_measurement_reflns_used    7776
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.54
_cell_measurement_theta_min      2.41
_cell_volume                     1006.83(6)
_computing_cell_refinement       'SAINT+ v. 7.06 a (Bruker AXS, 2003)'
_computing_data_collection       'APEX-W2K-NT v. 1.0 (Bruker AXS, 2004)'
_computing_data_reduction        'SAINT+ v. 7.06 a (Bruker AXS, 2001)'
_computing_molecular_graphics    'XP, SHELXTL v. 6.10 (Bruker, 2000)'
_computing_publication_material  'XCIF, SHELXTL v. 6.12 (Bruker, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
  Bruker-Nonius X8kappa APEX II CCD area detector'
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_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  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11848
_diffrn_reflns_theta_full        30.56
_diffrn_reflns_theta_max         30.56
_diffrn_reflns_theta_min         2.29
_diffrn_standards_number         'no decay'
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_T_max  0.9698
_exptl_absorpt_correction_T_min  0.9105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  SADABS: Area-Detector Absorption Correction. Bruker-AXS
  within v. 7.06 a (Bruker AXS, 2003).
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         3088
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0240
_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)+(0.0421P)²+0.1454P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0648
_refine_ls_wR_factor_ref         0.0657
_reflns_number_gt                2999
_reflns_number_total             3088
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol050080hsi20050118_063001.cif
_cod_data_source_block           (Ss)-4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1506512
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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 0.43419(4) 0.82213(2) 0.158776(13) 0.01563(6) Uani 1 1 d .
O1 O 0.26446(13) 0.77046(8) 0.21420(4) 0.02075(15) Uani 1 1 d .
N1 N 0.45197(16) 0.71290(8) 0.08369(5) 0.01731(16) Uani 1 1 d .
C1 C 0.29155(18) 0.62418(10) 0.07720(6) 0.01614(17) Uani 1 1 d .
H1 H 0.1737 0.6234 0.1136 0.019 Uiso 1 1 d R
C2 C 0.28425(18) 0.52344(10) 0.01511(5) 0.01582(17) Uani 1 1 d .
C3 C 0.46307(19) 0.51219(11) -0.03646(5) 0.01852(19) Uani 1 1 d .
H3 H 0.5931 0.5697 -0.0314 0.022 Uiso 1 1 d R
C4 C 0.4498(2) 0.41687(11) -0.09494(6) 0.0217(2) Uani 1 1 d .
H4 H 0.5711 0.4093 -0.1299 0.026 Uiso 1 1 d R
C5 C 0.2589(2) 0.33186(12) -0.10277(6) 0.0223(2) Uani 1 1 d .
H5 H 0.2497 0.2678 -0.1434 0.027 Uiso 1 1 d R
C6 C 0.0827(2) 0.34097(11) -0.05111(6) 0.0217(2) Uani 1 1 d .
H6 H -0.0461 0.2823 -0.0559 0.026 Uiso 1 1 d R
C7 C 0.09566(18) 0.43668(10) 0.00790(6) 0.01894(18) Uani 1 1 d .
H7 H -0.0245 0.4428 0.0434 0.023 Uiso 1 1 d R
C8 C 0.71404(16) 0.77984(10) 0.19618(6) 0.01521(17) Uani 1 1 d .
H8 H 0.8301 0.8032 0.1571 0.018 Uiso 1 1 d R
C9 C 0.73498(18) 0.62596(10) 0.21533(6) 0.01988(19) Uani 1 1 d .
H9A H 0.8893 0.6063 0.2328 0.030 Uiso 1 1 d R
H9B H 0.7025 0.5702 0.1704 0.030 Uiso 1 1 d R
H9C H 0.6266 0.6024 0.2552 0.030 Uiso 1 1 d R
C10 C 0.75261(18) 0.87320(11) 0.26445(6) 0.01959(19) Uani 1 1 d .
H10A H 0.6435 0.8492 0.3040 0.029 Uiso 1 1 d R
H10B H 0.7320 0.9707 0.2498 0.029 Uiso 1 1 d R
H10C H 0.9070 0.8597 0.2834 0.029 Uiso 1 1 d R
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
S1 0.01536(10) 0.01391(10) 0.01762(10) -0.00045(8) -0.00214(9) 0.00132(8)
O1 0.0136(3) 0.0277(4) 0.0210(3) -0.0050(3) 0.0017(3) -0.0001(3)
N1 0.0207(4) 0.0169(3) 0.0144(3) 0.0003(3) -0.0008(3) -0.0004(3)
C1 0.0164(4) 0.0165(4) 0.0155(4) 0.0011(3) -0.0009(3) 0.0011(3)
C2 0.0178(4) 0.0150(4) 0.0147(4) 0.0011(3) -0.0012(4) 0.0011(3)
C3 0.0190(5) 0.0191(4) 0.0174(4) 0.0015(3) 0.0012(4) -0.0004(4)
C4 0.0242(5) 0.0242(4) 0.0166(4) 0.0006(3) 0.0026(4) 0.0027(4)
C5 0.0286(5) 0.0208(4) 0.0176(4) -0.0026(4) -0.0044(4) 0.0039(4)
C6 0.0235(5) 0.0188(4) 0.0229(4) -0.0004(4) -0.0055(4) -0.0018(4)
C7 0.0177(4) 0.0197(4) 0.0195(4) -0.0002(3) -0.0002(4) -0.0004(4)
C8 0.0123(4) 0.0149(4) 0.0184(4) -0.0002(3) 0.0003(3) -0.0003(3)
C9 0.0185(4) 0.0157(4) 0.0255(5) 0.0012(4) -0.0034(4) 0.0011(4)
C10 0.0164(4) 0.0207(4) 0.0217(5) -0.0044(4) -0.0023(4) -0.0006(4)
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
O1 S1 N1 110.74(4)
O1 S1 C8 107.08(5)
N1 S1 C8 95.29(4)
C1 N1 S1 115.87(7)
N1 C1 C2 121.93(9)
N1 C1 H1 119.0
C2 C1 H1 119.0
C7 C2 C3 119.62(9)
C7 C2 C1 119.07(9)
C3 C2 C1 121.31(9)
C4 C3 C2 119.85(10)
C4 C3 H3 120.1
C2 C3 H3 120.1
C3 C4 C5 120.37(10)
C3 C4 H4 119.8
C5 C4 H4 119.8
C6 C5 C4 120.03(10)
C6 C5 H5 120.0
C4 C5 H5 120.0
C5 C6 C7 119.75(10)
C5 C6 H6 120.1
C7 C6 H6 120.1
C2 C7 C6 120.37(10)
C2 C7 H7 119.8
C6 C7 H7 119.8
C9 C8 C10 112.42(8)
C9 C8 S1 111.77(7)
C10 C8 S1 107.06(7)
C9 C8 H8 108.5
C10 C8 H8 108.5
S1 C8 H8 108.5
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C8 C10 H10A 109.5
C8 C10 H10B 109.4
H10A C10 H10B 109.5
C8 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4894(8)
S1 N1 1.7002(9)
S1 C8 1.8257(10)
N1 C1 1.2791(13)
C1 C2 1.4678(13)
C1 H1 0.9500
C2 C7 1.3963(14)
C2 C3 1.4014(14)
C3 C4 1.3870(14)
C3 H3 0.9500
C4 C5 1.3985(16)
C4 H4 0.9500
C5 C6 1.3891(16)
C5 H5 0.9500
C6 C7 1.3963(14)
C6 H6 0.9500
C7 H7 0.9500
C8 C9 1.5221(14)
C8 C10 1.5252(13)
C8 H8 1.0000
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
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
C1 H1 O1 0.95 2.34 2.8143(12) 110.4
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
O1 S1 N1 C1 14.47(9)
C8 S1 N1 C1 124.98(8)
S1 N1 C1 C2 179.90(7)
N1 C1 C2 C7 -175.03(10)
N1 C1 C2 C3 5.44(15)
C7 C2 C3 C4 1.12(15)
C1 C2 C3 C4 -179.35(9)
C2 C3 C4 C5 0.01(15)
C3 C4 C5 C6 -1.05(16)
C4 C5 C6 C7 0.95(16)
C3 C2 C7 C6 -1.22(15)
C1 C2 C7 C6 179.24(9)
C5 C6 C7 C2 0.19(15)
O1 S1 C8 C9 53.69(8)
N1 S1 C8 C9 -59.92(8)
O1 S1 C8 C10 -69.83(7)
N1 S1 C8 C10 176.56(7)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 21200099 ChemSpider
