#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/26/4022697.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_4022697
loop_
_publ_author_name
'Paul Evans'
_publ_section_title
;
 The Double Reduction of Cyclic Sulfonamides for the Synthesis of
 (4S-Phenylpyrrolidin-2R-yl)methanol and 2S-Methyl-4S-phenylpyrrolidine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1830
_journal_page_last               1833
_journal_paper_doi               10.1021/jo062189o
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_sum            'C11 H13 N O2 S'
_chemical_formula_weight         223.28
_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   difmap
_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                   8.9647(10)
_cell_length_b                   9.7275(11)
_cell_length_c                   12.0253(13)
_cell_measurement_reflns_used    7141
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.09
_cell_measurement_theta_min      2.27
_cell_volume                     1048.7(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, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9560
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         2.69
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  0.8700
_exptl_absorpt_correction_T_min  0.6985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       pyramid
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2504
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0309
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0573P)²+0.0891P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0790
_reflns_number_gt                2424
_reflns_number_total             2504
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062189osi20061207_073035.cif
_cod_data_source_block           eva03
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4022697
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
O1 O 0.18332(13) 0.70501(12) 0.87934(9) 0.0254(2) Uani 1 1 d
O2 O -0.01345(12) 0.82615(11) 0.77806(9) 0.0252(2) Uani 1 1 d
S S 0.14251(4) 0.79702(3) 0.79183(3) 0.01771(10) Uani 1 1 d
C1 C 0.21068(15) 0.73574(14) 0.66396(11) 0.0163(3) Uani 1 1 d
C2 C 0.17334(16) 0.60220(14) 0.63335(13) 0.0201(3) Uani 1 1 d
H2 H 0.119(2) 0.551(2) 0.6793(14) 0.018(4) Uiso 1 1 d
C3 C 0.21687(17) 0.55423(18) 0.52980(14) 0.0254(3) Uani 1 1 d
H3 H 0.197(2) 0.461(2) 0.5105(17) 0.031(5) Uiso 1 1 d
C4 C 0.29583(18) 0.63864(19) 0.45911(14) 0.0282(3) Uani 1 1 d
H4 H 0.323(2) 0.607(2) 0.3901(19) 0.033(5) Uiso 1 1 d
C5 C 0.33302(18) 0.77158(18) 0.49038(13) 0.0256(3) Uani 1 1 d
H5 H 0.389(2) 0.828(2) 0.4389(17) 0.032(5) Uiso 1 1 d
C6 C 0.29088(15) 0.82330(15) 0.59440(12) 0.0192(3) Uani 1 1 d
C7 C 0.33704(18) 0.96520(15) 0.63205(13) 0.0238(3) Uani 1 1 d
H7 H 0.355(3) 1.022(2) 0.5710(16) 0.038(6) Uiso 1 1 d
C8 C 0.21412(18) 1.02772(14) 0.70472(14) 0.0251(3) Uani 1 1 d
H8A H 0.111(2) 1.0206(18) 0.6758(14) 0.017(4) Uiso 1 1 d
H8B H 0.236(2) 1.117(2) 0.7261(16) 0.026(5) Uiso 1 1 d
N N 0.22701(14) 0.94588(13) 0.80942(10) 0.0219(3) Uani 1 1 d
C9 C 0.39317(18) 0.94996(17) 0.83142(13) 0.0256(3) Uani 1 1 d
H9 H 0.4057(19) 1.040(2) 0.8642(16) 0.023(5) Uiso 1 1 d
C11 C 0.4561(2) 0.8434(2) 0.90952(16) 0.0348(4) Uani 1 1 d
H11A H 0.552(3) 0.864(3) 0.926(2) 0.050(7) Uiso 1 1 d
H11B H 0.456(2) 0.752(2) 0.8780(18) 0.023(4) Uiso 1 1 d
H11C H 0.411(3) 0.845(3) 0.977(3) 0.070(9) Uiso 1 1 d
C10 C 0.46763(17) 0.95385(17) 0.71546(15) 0.0279(3) Uani 1 1 d
H10A H 0.527(2) 0.872(2) 0.698(2) 0.044(6) Uiso 1 1 d
H10B H 0.528(2) 1.031(3) 0.708(2) 0.041(6) 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
O1 S O2 117.24(7)
O1 S N 109.76(7)
O2 S N 106.80(7)
O1 S C1 110.04(7)
O2 S C1 107.72(7)
N S C1 104.49(7)
C2 C1 C6 122.42(13)
C2 C1 S 117.66(11)
C6 C1 S 119.79(11)
C3 C2 C1 118.98(14)
C3 C2 H2 121.8(11)
C1 C2 H2 119.2(12)
C4 C3 C2 119.89(15)
C4 C3 H3 120.8(12)
C2 C3 H3 119.2(12)
C3 C4 C5 120.79(15)
C3 C4 H4 119.7(13)
C5 C4 H4 119.5(13)
C4 C5 C6 120.81(14)
C4 C5 H5 118.5(13)
C6 C5 H5 120.6(13)
C1 C6 C5 117.11(13)
C1 C6 C7 121.33(13)
C5 C6 C7 121.48(13)
C6 C7 C8 109.68(12)
C6 C7 C10 109.68(12)
C8 C7 C10 101.71(13)
C6 C7 H7 110.8(13)
C8 C7 H7 109.8(13)
C10 C7 H7 114.8(14)
N C8 C7 102.32(11)
N C8 H8A 109.3(10)
C7 C8 H8A 116.4(10)
N C8 H8B 104.4(12)
C7 C8 H8B 112.4(12)
H8A C8 H8B 111.0(16)
C8 N C9 102.09(12)
C8 N S 108.94(10)
C9 N S 119.87(10)
C11 C9 N 117.34(14)
C11 C9 C10 114.63(14)
N C9 C10 105.54(12)
C11 C9 H9 109.1(11)
N C9 H9 102.1(10)
C10 C9 H9 107.1(11)
C9 C11 H11A 109.8(17)
C9 C11 H11B 112.9(12)
H11A C11 H11B 107(2)
C9 C11 H11C 112(2)
H11A C11 H11C 103(2)
H11B C11 H11C 111(2)
C7 C10 C9 105.07(12)
C7 C10 H10A 109.1(15)
C9 C10 H10A 114.1(14)
C7 C10 H10B 108.5(14)
C9 C10 H10B 111.1(15)
H10A C10 H10B 108.8(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 S 1.4291(11)
O2 S 1.4361(11)
S N 1.6479(13)
S C1 1.7588(14)
C1 C2 1.3911(19)
C1 C6 1.3936(19)
C2 C3 1.386(2)
C2 H2 0.889(19)
C3 C4 1.378(3)
C3 H3 0.95(2)
C4 C5 1.387(2)
C4 H4 0.92(2)
C5 C6 1.400(2)
C5 H5 0.97(2)
C6 C7 1.510(2)
C7 C8 1.532(2)
C7 C10 1.546(2)
C7 H7 0.93(2)
C8 N 1.494(2)
C8 H8A 0.993(18)
C8 H8B 0.92(2)
N C9 1.513(2)
C9 C11 1.508(2)
C9 C10 1.546(2)
C9 H9 0.97(2)
C11 H11A 0.90(3)
C11 H11B 0.97(2)
C11 H11C 0.91(3)
C10 H10A 0.98(2)
C10 H10B 0.93(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
O1 S C1 C2 54.14(12)
O2 S C1 C2 -74.76(12)
N S C1 C2 171.92(10)
O1 S C1 C6 -129.85(11)
O2 S C1 C6 101.25(12)
N S C1 C6 -12.07(13)
C6 C1 C2 C3 -0.2(2)
S C1 C2 C3 175.68(11)
C1 C2 C3 C4 0.0(2)
C2 C3 C4 C5 0.2(2)
C3 C4 C5 C6 -0.2(2)
C2 C1 C6 C5 0.2(2)
S C1 C6 C5 -175.57(11)
C2 C1 C6 C7 -176.71(13)
S C1 C6 C7 7.48(18)
C4 C5 C6 C1 -0.1(2)
C4 C5 C6 C7 176.90(14)
C1 C6 C7 C8 -36.59(18)
C5 C6 C7 C8 146.59(14)
C1 C6 C7 C10 74.32(17)
C5 C6 C7 C10 -102.51(16)
C6 C7 C8 N 71.95(14)
C10 C7 C8 N -44.11(14)
C7 C8 N C9 47.74(14)
C7 C8 N S -79.99(13)
O1 S N C8 166.16(10)
O2 S N C8 -65.79(11)
C1 S N C8 48.19(11)
O1 S N C9 49.26(13)
O2 S N C9 177.31(11)
C1 S N C9 -68.71(12)
C8 N C9 C11 -161.48(14)
S N C9 C11 -41.10(18)
C8 N C9 C10 -32.38(14)
S N C9 C10 88.00(14)
C6 C7 C10 C9 -92.66(15)
C8 C7 C10 C9 23.40(15)
C11 C9 C10 C7 135.71(14)
N C9 C10 C7 5.03(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17268827
