#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:47:24 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178444 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/65/4026541.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_4026541
loop_
_publ_author_name
'Vladimir S. Yarmolchuk'
'Ivan L. Mukan'
'Oleksandr O. Grygorenko'
'Andrey A. Tolmachev'
'Svitlana V. Shishkina'
'Oleg V. Shishkin'
'Igor V. Komarov'
_publ_section_title
;
 An Entry into Hexahydro-2H-thieno[2,3-c]pyrrole 1,1-Dioxide Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7010
_journal_page_last               7016
_journal_paper_doi               10.1021/jo200878t
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C14 H19 N O3 S'
_chemical_formula_weight         281.36
_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                 92.578(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6298(2)
_cell_length_b                   7.9932(2)
_cell_length_c                   26.5748(8)
_cell_measurement_temperature    293(2)
_cell_volume                     1406.86(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            12825
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.97
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  0.9770
_exptl_absorpt_correction_T_min  0.9332
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.041
_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     248
_refine_ls_number_reflns         4027
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0346
_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)+(0.0623P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.1005
_reflns_number_gt                3229
_reflns_number_total             4027
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200878t_si_005.cif
_cod_data_source_block           tolm109
_cod_database_code               4026541
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
S1 S 0.45874(4) 0.25182(3) 0.061817(9) 0.03262(9) Uani 1 1 d
N1 N 0.71681(13) 0.41409(12) 0.15337(3) 0.0338(2) Uani 1 1 d
O1 O 0.34164(13) 0.19606(13) 0.10307(3) 0.0481(2) Uani 1 1 d
O2 O 0.35939(13) 0.24871(11) 0.01242(3) 0.0447(2) Uani 1 1 d
O3 O 0.80137(12) 0.30461(12) -0.01241(3) 0.04132(19) Uani 1 1 d
C1 C 0.69071(16) 0.14083(14) 0.05968(4) 0.0355(2) Uani 1 1 d
H1B H 0.669(2) 0.043(2) 0.0399(6) 0.050(4) Uiso 1 1 d
H1A H 0.726(2) 0.1091(18) 0.0957(5) 0.046(3) Uiso 1 1 d
C2 C 0.83770(16) 0.27044(14) 0.03966(4) 0.0343(2) Uani 1 1 d
H2 H 0.970(2) 0.2342(16) 0.0463(5) 0.037(3) Uiso 1 1 d
C3 C 0.79788(16) 0.43506(14) 0.06697(4) 0.0349(2) Uani 1 1 d
H3 H 0.846(2) 0.5244(18) 0.0460(5) 0.044(4) Uiso 1 1 d
C4 C 0.88817(17) 0.44153(17) 0.12126(4) 0.0408(3) Uani 1 1 d
H4B H 0.996(2) 0.364(2) 0.1281(5) 0.052(4) Uiso 1 1 d
H4A H 0.945(3) 0.555(2) 0.1276(6) 0.066(5) Uiso 1 1 d
C5 C 0.55262(17) 0.50848(15) 0.12831(4) 0.0369(2) Uani 1 1 d
H5B H 0.4199(19) 0.4849(15) 0.1415(4) 0.034(3) Uiso 1 1 d
H5A H 0.574(2) 0.631(2) 0.1297(5) 0.045(3) Uiso 1 1 d
C6 C 0.56869(16) 0.45665(14) 0.07356(4) 0.0334(2) Uani 1 1 d
H6 H 0.508(2) 0.5285(19) 0.0470(5) 0.050(4) Uiso 1 1 d
C7 C 0.76363(19) 0.46380(18) 0.20542(4) 0.0413(3) Uani 1 1 d
H7B H 0.789(2) 0.591(2) 0.2075(6) 0.063(4) Uiso 1 1 d
H7A H 0.883(2) 0.413(2) 0.2160(5) 0.051(4) Uiso 1 1 d
C8 C 0.60222(17) 0.42112(14) 0.24163(4) 0.0351(2) Uani 1 1 d
C9 C 0.6074(2) 0.49918(16) 0.28877(4) 0.0426(3) Uani 1 1 d
H9 H 0.705(2) 0.581(2) 0.2975(6) 0.053(4) Uiso 1 1 d
C10 C 0.4602(2) 0.46680(19) 0.32267(5) 0.0516(3) Uani 1 1 d
H10 H 0.465(3) 0.536(3) 0.3547(8) 0.086(6) Uiso 1 1 d
C11 C 0.3062(2) 0.3562(2) 0.31053(5) 0.0533(3) Uani 1 1 d
H11 H 0.206(3) 0.339(2) 0.3340(7) 0.073(5) Uiso 1 1 d
C12 C 0.3012(2) 0.27519(18) 0.26441(5) 0.0475(3) Uani 1 1 d
H12 H 0.201(2) 0.197(2) 0.2536(6) 0.053(4) Uiso 1 1 d
C13 C 0.44841(18) 0.30797(16) 0.23006(4) 0.0394(2) Uani 1 1 d
H13 H 0.444(2) 0.2512(17) 0.1994(6) 0.048(4) Uiso 1 1 d
C14 C 0.8625(3) 0.1759(2) -0.04460(6) 0.0591(4) Uani 1 1 d
H14C H 0.854(4) 0.213(3) -0.0751(9) 0.094(7) Uiso 1 1 d
H14B H 0.777(4) 0.088(3) -0.0428(9) 0.110(8) Uiso 1 1 d
H14A H 1.023(4) 0.146(3) -0.0373(9) 0.114(7) 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 S1 O2 116.56(5)
O1 S1 C1 111.46(6)
O2 S1 C1 108.82(5)
O1 S1 C6 111.97(5)
O2 S1 C6 109.62(5)
C1 S1 C6 96.57(5)
C7 N1 C5 114.46(9)
C7 N1 C4 111.92(9)
C5 N1 C4 103.79(9)
C14 O3 C2 114.22(11)
C2 C1 S1 103.76(8)
O3 C2 C3 105.74(9)
O3 C2 C1 112.66(9)
C3 C2 C1 106.86(9)
C2 C3 C4 113.92(10)
C2 C3 C6 109.92(9)
C4 C3 C6 103.47(8)
N1 C4 C3 105.16(9)
N1 C5 C6 102.28(8)
C5 C6 C3 104.48(9)
C5 C6 S1 111.44(8)
C3 C6 S1 105.61(7)
N1 C7 C8 114.58(9)
C13 C8 C9 118.53(11)
C13 C8 C7 122.75(10)
C9 C8 C7 118.72(11)
C10 C9 C8 120.71(12)
C11 C10 C9 120.33(12)
C10 C11 C12 119.71(12)
C11 C12 C13 120.17(13)
C8 C13 C12 120.53(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4421(8)
S1 O2 1.4422(9)
S1 C1 1.7785(11)
S1 C6 1.8135(11)
N1 C7 1.4591(14)
N1 C5 1.4602(14)
N1 C4 1.4677(14)
O3 C14 1.4089(17)
O3 C2 1.4203(14)
C1 C2 1.5340(16)
C2 C3 1.5314(15)
C3 C4 1.5378(16)
C3 C6 1.5470(15)
C5 C6 1.5213(15)
C7 C8 1.5100(16)
C8 C13 1.3871(16)
C8 C9 1.3986(16)
C9 C10 1.3820(19)
C10 C11 1.377(2)
C11 C12 1.385(2)
C12 C13 1.3911(18)
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 C1 C2 -146.94(7)
O2 S1 C1 C2 83.15(8)
C6 S1 C1 C2 -30.19(8)
C14 O3 C2 C3 169.89(11)
C14 O3 C2 C1 -73.73(13)
S1 C1 C2 O3 -72.77(10)
S1 C1 C2 C3 42.94(10)
O3 C2 C3 C4 -162.55(8)
C1 C2 C3 C4 77.20(11)
O3 C2 C3 C6 81.87(10)
C1 C2 C3 C6 -38.38(12)
C7 N1 C4 C3 -163.42(10)
C5 N1 C4 C3 -39.48(11)
C2 C3 C4 N1 -102.80(11)
C6 C3 C4 N1 16.50(12)
C7 N1 C5 C6 168.58(9)
C4 N1 C5 C6 46.32(11)
N1 C5 C6 C3 -34.99(11)
N1 C5 C6 S1 78.58(9)
C2 C3 C6 C5 133.20(9)
C4 C3 C6 C5 11.17(11)
C2 C3 C6 S1 15.55(10)
C4 C3 C6 S1 -106.47(8)
O1 S1 C6 C5 12.42(9)
O2 S1 C6 C5 143.40(8)
C1 S1 C6 C5 -103.91(8)
O1 S1 C6 C3 125.29(7)
O2 S1 C6 C3 -103.74(8)
C1 S1 C6 C3 8.95(8)
C5 N1 C7 C8 68.75(14)
C4 N1 C7 C8 -173.53(10)
N1 C7 C8 C13 15.87(18)
N1 C7 C8 C9 -163.93(11)
C13 C8 C9 C10 -1.28(19)
C7 C8 C9 C10 178.52(13)
C8 C9 C10 C11 0.3(2)
C9 C10 C11 C12 1.0(2)
C10 C11 C12 C13 -1.4(2)
C9 C8 C13 C12 0.97(18)
C7 C8 C13 C12 -178.83(12)
C11 C12 C13 C8 0.3(2)
