#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/46/4024620.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_4024620
loop_
_publ_author_name
'Ali Reza Modarresi-Alam'
'Homeyra Alsadat Amirazizi'
'Hajar Bagheri'
'Hamid-Reza Bijanzadeh'
'Erich Kleinpeter'
_publ_section_title
;
Dynamic 1H NMR Spectroscopic Study of the Ring Inversion in N-Sulfonyl
Morpholines-Studies on N-S Interactions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4740
_journal_page_last               4746
_journal_paper_doi               10.1021/jo900454a
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C11 H15 N O3 S'
_chemical_formula_weight         241.30
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 111.694(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.068(2)
_cell_length_b                   18.294(3)
_cell_length_c                   8.815(2)
_cell_measurement_reflns_used    10013
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      29.51
_cell_measurement_theta_min      2.17
_cell_volume                     1208.8(5)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      210(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      ' 180 frames, detector distance = 100 mm'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method, delta omega = 1.0 deg'
_diffrn_radiation_collimation    '0.5 mm diameter, multiple pinhole'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0986
_diffrn_reflns_av_sigmaI/netI    0.0569
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7731
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.23
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           40
_diffrn_source_power             2.00
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.26
_exptl_absorpt_correction_T_max  0.9040
_exptl_absorpt_correction_T_min  0.9033
_exptl_absorpt_correction_type   sphere
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.475
_exptl_crystal_size_min          0.235
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2126
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0381
_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)+(0.0572P)²+0.1618P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1076
_reflns_number_gt                1820
_reflns_number_total             2126
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900454a_si_002.cif
_cod_data_source_block           kp5ni
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4024620
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.3938(2) 0.36970(11) 0.9233(2) 0.0529(5) Uani 1 1 d . . .
H1 H 0.4522 0.3288 0.9047 0.064 Uiso 1 1 calc R . .
C2 C 0.4354(3) 0.39635(12) 1.0805(2) 0.0590(5) Uani 1 1 d . . .
H2 H 0.5224 0.3727 1.1669 0.071 Uiso 1 1 calc R . .
C3 C 0.3511(3) 0.45702(11) 1.1123(2) 0.0531(5) Uani 1 1 d . . .
C4 C 0.3974(4) 0.48621(15) 1.2835(3) 0.0798(7) Uani 1 1 d . . .
H4A H 0.2931 0.4853 1.3114 0.096 Uiso 1 1 calc R . .
H4B H 0.4397 0.5355 1.2888 0.096 Uiso 1 1 calc R . .
H4C H 0.4887 0.4563 1.3589 0.096 Uiso 1 1 calc R . .
C5 C 0.2215(3) 0.49109(11) 0.9802(3) 0.0589(5) Uani 1 1 d . . .
H5 H 0.1625 0.5318 0.9989 0.071 Uiso 1 1 calc R . .
C6 C 0.1779(3) 0.46616(10) 0.8219(2) 0.0516(4) Uani 1 1 d . . .
H6 H 0.0921 0.4901 0.7352 0.062 Uiso 1 1 calc R . .
C7 C 0.2643(2) 0.40487(9) 0.79460(19) 0.0411(4) Uani 1 1 d . . .
C8 C -0.1278(2) 0.34038(13) 0.5639(2) 0.0583(5) Uani 1 1 d . . .
H8A H -0.1603 0.3815 0.4893 0.070 Uiso 1 1 calc R . .
H8B H -0.1179 0.3574 0.6711 0.070 Uiso 1 1 calc R . .
C9 C -0.2689(3) 0.28135(15) 0.5054(3) 0.0756(7) Uani 1 1 d . . .
H9A H -0.3821 0.3006 0.5024 0.091 Uiso 1 1 calc R . .
H9B H -0.2832 0.2668 0.3955 0.091 Uiso 1 1 calc R . .
C10 C -0.0584(4) 0.18869(13) 0.6130(3) 0.0780(7) Uani 1 1 d . . .
H10A H -0.0719 0.1733 0.5038 0.094 Uiso 1 1 calc R . .
H10B H -0.0296 0.1459 0.6830 0.094 Uiso 1 1 calc R . .
C11 C 0.0922(3) 0.24336(11) 0.6752(2) 0.0565(5) Uani 1 1 d . . .
H11A H 0.1128 0.2561 0.7875 0.068 Uiso 1 1 calc R . .
H11B H 0.2010 0.2223 0.6715 0.068 Uiso 1 1 calc R . .
N1 N 0.04360(18) 0.30956(8) 0.57135(16) 0.0450(4) Uani 1 1 d . . .
O1 O 0.12824(19) 0.42707(8) 0.48030(15) 0.0622(4) Uani 1 1 d . . .
O2 O 0.35117(18) 0.32831(9) 0.58549(17) 0.0654(4) Uani 1 1 d . . .
O3 O -0.2217(2) 0.21917(11) 0.60989(18) 0.0853(6) Uani 1 1 d . . .
S1 S 0.20425(6) 0.36908(3) 0.59495(5) 0.04571(18) 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
C7 C1 C2 119.03(18) . . ?
C3 C2 C1 121.92(17) . . ?
C2 C3 C5 117.61(17) . . ?
C2 C3 C4 121.8(2) . . ?
C5 C3 C4 120.6(2) . . ?
C6 C5 C3 121.86(18) . . ?
C5 C6 C7 118.98(17) . . ?
C1 C7 C6 120.59(16) . . ?
C1 C7 S1 119.29(14) . . ?
C6 C7 S1 120.09(13) . . ?
N1 C8 C9 108.52(19) . . ?
O3 C9 C8 111.21(16) . . ?
O3 C10 C11 111.27(19) . . ?
N1 C11 C10 108.86(16) . . ?
C8 N1 C11 111.76(15) . . ?
C8 N1 S1 115.78(13) . . ?
C11 N1 S1 116.52(11) . . ?
C10 O3 C9 110.53(16) . . ?
O2 S1 O1 119.47(9) . . ?
O2 S1 N1 106.18(9) . . ?
O1 S1 N1 106.74(8) . . ?
O2 S1 C7 108.86(8) . . ?
O1 S1 C7 108.37(8) . . ?
N1 S1 C7 106.49(7) . . ?
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 C7 1.384(2) . ?
C1 C2 1.388(3) . ?
C2 C3 1.383(3) . ?
C3 C5 1.392(3) . ?
C3 C4 1.512(3) . ?
C5 C6 1.384(3) . ?
C6 C7 1.387(3) . ?
C7 S1 1.7691(17) . ?
C8 N1 1.472(2) . ?
C8 C9 1.515(3) . ?
C9 O3 1.424(3) . ?
C10 O3 1.421(3) . ?
C10 C11 1.512(3) . ?
C11 N1 1.481(2) . ?
N1 S1 1.6461(15) . ?
O1 S1 1.4369(14) . ?
O2 S1 1.4287(15) . ?
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
C7 C1 C2 C3 0.0(3) . . . . ?
C1 C2 C3 C5 0.0(3) . . . . ?
C1 C2 C3 C4 -179.62(19) . . . . ?
C2 C3 C5 C6 -0.5(3) . . . . ?
C4 C3 C5 C6 179.17(18) . . . . ?
C3 C5 C6 C7 0.9(3) . . . . ?
C2 C1 C7 C6 0.4(3) . . . . ?
C2 C1 C7 S1 -177.47(15) . . . . ?
C5 C6 C7 C1 -0.9(3) . . . . ?
C5 C6 C7 S1 177.03(14) . . . . ?
N1 C8 C9 O3 57.7(2) . . . . ?
O3 C10 C11 N1 -56.9(2) . . . . ?
C9 C8 N1 C11 -55.69(19) . . . . ?
C9 C8 N1 S1 167.70(13) . . . . ?
C10 C11 N1 C8 55.4(2) . . . . ?
C10 C11 N1 S1 -168.30(15) . . . . ?
C11 C10 O3 C9 60.2(2) . . . . ?
C8 C9 O3 C10 -60.6(2) . . . . ?
C8 N1 S1 O2 -175.38(12) . . . . ?
C11 N1 S1 O2 50.09(14) . . . . ?
C8 N1 S1 O1 -46.90(14) . . . . ?
C11 N1 S1 O1 178.57(13) . . . . ?
C8 N1 S1 C7 68.71(13) . . . . ?
C11 N1 S1 C7 -65.81(14) . . . . ?
C1 C7 S1 O2 -25.61(17) . . . . ?
C6 C7 S1 O2 156.47(14) . . . . ?
C1 C7 S1 O1 -157.00(15) . . . . ?
C6 C7 S1 O1 25.08(16) . . . . ?
C1 C7 S1 N1 88.49(16) . . . . ?
C6 C7 S1 N1 -89.43(15) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 72830
