#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/72/1507259.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_1507259
loop_
_publ_author_name
'Williams, Andrew J.'
'Chakthong, Suda'
'Gray, Diane'
'Lawrence, Ron M.'
'Gallagher, Timothy'
_publ_section_title
;
 1,2-cyclic sulfamidates as versatile precursors to thiomorpholines and
 piperazines.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              811
_journal_page_last               814
_journal_paper_doi               10.1021/ol027418h
_journal_volume                  5
_journal_year                    2003
_chemical_formula_moiety         'C12 H15 N O S'
_chemical_formula_sum            'C12 H15 N O S'
_chemical_formula_weight         221.31
_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                   7.9050(16)
_cell_length_b                   11.582(2)
_cell_length_c                   12.200(2)
_cell_measurement_reflns_used    2251
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.09
_cell_measurement_theta_min      2.42
_cell_volume                     1117.0(3)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'ω 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  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7877
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.42
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2547
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0355
_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)+(0.0462P)²+0.1675P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0844
_reflns_number_gt                2443
_reflns_number_total             2547
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ol027418hsi20021206_110926.cif
_cod_data_source_block           5b
_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_cell_volume        1117.0(4)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1507259
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
C1 C 0.8727(2) 0.14910(18) 0.50566(14) 0.0203(4) Uani 1 1 d .
H1A H 0.8893 0.1049 0.5743 0.024 Uiso 1 1 calc R
H1B H 0.8793 0.2323 0.5237 0.024 Uiso 1 1 calc R
C2 C 0.6995(2) 0.12232(16) 0.45920(14) 0.0162(3) Uani 1 1 d .
C4 C 0.7859(2) 0.20573(16) 0.27474(14) 0.0144(4) Uani 1 1 d .
H4 H 0.7878 0.1617 0.2042 0.017 Uiso 1 1 calc R
C5 C 0.9714(2) 0.22156(15) 0.31232(13) 0.0135(3) Uani 1 1 d .
H5 H 0.9809 0.2988 0.3484 0.016 Uiso 1 1 calc R
C6 C 0.5137(2) 0.10471(18) 0.30266(15) 0.0204(4) Uani 1 1 d .
H6A H 0.4559 0.0521 0.3532 0.031 Uiso 1 1 calc R
H6B H 0.5363 0.0647 0.2334 0.031 Uiso 1 1 calc R
H6C H 0.4418 0.1721 0.2888 0.031 Uiso 1 1 calc R
C7 C 0.7129(2) 0.32554(17) 0.25038(16) 0.0213(4) Uani 1 1 d .
H7A H 0.6030 0.3173 0.2140 0.032 Uiso 1 1 calc R
H7B H 0.7905 0.3679 0.2024 0.032 Uiso 1 1 calc R
H7C H 0.6985 0.3681 0.3192 0.032 Uiso 1 1 calc R
C8 C 1.0906(2) 0.22029(15) 0.21502(13) 0.0126(3) Uani 1 1 d .
C9 C 1.1825(2) 0.31881(15) 0.18780(14) 0.0162(4) Uani 1 1 d .
H9 H 1.1696 0.3872 0.2299 0.019 Uiso 1 1 calc R
C10 C 1.2935(2) 0.31735(17) 0.09899(16) 0.0204(4) Uani 1 1 d .
H10 H 1.3549 0.3850 0.0800 0.024 Uiso 1 1 calc R
C11 C 1.3140(2) 0.21704(18) 0.03834(14) 0.0210(4) Uani 1 1 d .
H11 H 1.3923 0.2153 -0.0207 0.025 Uiso 1 1 calc R
C12 C 1.2208(2) 0.11960(18) 0.06359(14) 0.0199(4) Uani 1 1 d .
H12 H 1.2332 0.0516 0.0208 0.024 Uiso 1 1 calc R
C13 C 1.1094(2) 0.12103(17) 0.15140(14) 0.0166(4) Uani 1 1 d .
H13 H 1.0453 0.0540 0.1683 0.020 Uiso 1 1 calc R
N3 N 0.67409(19) 0.14262(13) 0.35146(12) 0.0155(3) Uani 1 1 d .
O1 O 0.59086(17) 0.07950(11) 0.51850(10) 0.0206(3) Uani 1 1 d .
S1 S 1.03874(5) 0.11306(4) 0.41028(3) 0.01722(12) 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
C2 C1 S1 111.67(12)
C2 C1 H1A 109.3
S1 C1 H1A 109.3
C2 C1 H1B 109.3
S1 C1 H1B 109.3
H1A C1 H1B 107.9
O1 C2 N3 122.68(17)
O1 C2 C1 119.66(16)
N3 C2 C1 117.60(16)
N3 C4 C7 110.18(14)
N3 C4 C5 115.91(13)
C7 C4 C5 107.89(15)
N3 C4 H4 107.5
C7 C4 H4 107.5
C5 C4 H4 107.5
C8 C5 C4 110.85(14)
C8 C5 S1 109.07(12)
C4 C5 S1 113.03(12)
C8 C5 H5 107.9
C4 C5 H5 107.9
S1 C5 H5 107.9
N3 C6 H6A 109.5
N3 C6 H6B 109.5
H6A C6 H6B 109.5
N3 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C4 C7 H7A 109.5
C4 C7 H7B 109.5
H7A C7 H7B 109.5
C4 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C9 C8 C13 119.15(16)
C9 C8 C5 120.20(15)
C13 C8 C5 120.65(15)
C8 C9 C10 120.23(16)
C8 C9 H9 119.9
C10 C9 H9 119.9
C11 C10 C9 119.89(17)
C11 C10 H10 120.1
C9 C10 H10 120.1
C12 C11 C10 120.18(17)
C12 C11 H11 119.9
C10 C11 H11 119.9
C11 C12 C13 120.05(18)
C11 C12 H12 120.0
C13 C12 H12 120.0
C12 C13 C8 120.46(17)
C12 C13 H13 119.8
C8 C13 H13 119.8
C2 N3 C6 118.11(15)
C2 N3 C4 127.78(15)
C6 N3 C4 114.01(14)
C1 S1 C5 92.93(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.514(2)
C1 S1 1.8029(18)
C1 H1A 0.9900
C1 H1B 0.9900
C2 O1 1.228(2)
C2 N3 1.350(2)
C4 N3 1.480(2)
C4 C7 1.532(2)
C4 C5 1.547(2)
C4 H4 1.0000
C5 C8 1.516(2)
C5 S1 1.8141(17)
C5 H5 1.0000
C6 N3 1.468(2)
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 C9 1.393(2)
C8 C13 1.395(3)
C9 C10 1.394(3)
C9 H9 0.9500
C10 C11 1.387(3)
C10 H10 0.9500
C11 C12 1.382(3)
C11 H11 0.9500
C12 C13 1.387(2)
C12 H12 0.9500
C13 H13 0.9500
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
S1 C1 C2 O1 139.42(15)
S1 C1 C2 N3 -37.8(2)
N3 C4 C5 C8 147.13(15)
C7 C4 C5 C8 -88.83(17)
N3 C4 C5 S1 24.32(19)
C7 C4 C5 S1 148.36(13)
C4 C5 C8 C9 115.03(17)
S1 C5 C8 C9 -119.90(15)
C4 C5 C8 C13 -64.7(2)
S1 C5 C8 C13 60.36(18)
C13 C8 C9 C10 -0.9(3)
C5 C8 C9 C10 179.36(16)
C8 C9 C10 C11 -0.8(3)
C9 C10 C11 C12 2.0(3)
C10 C11 C12 C13 -1.5(3)
C11 C12 C13 C8 -0.2(3)
C9 C8 C13 C12 1.4(2)
C5 C8 C13 C12 -178.85(16)
O1 C2 N3 C6 -4.1(3)
C1 C2 N3 C6 173.07(16)
O1 C2 N3 C4 172.14(17)
C1 C2 N3 C4 -10.7(3)
C7 C4 N3 C2 -104.9(2)
C5 C4 N3 C2 17.9(3)
C7 C4 N3 C6 71.40(19)
C5 C4 N3 C6 -165.76(15)
C2 C1 S1 C5 65.22(15)
C8 C5 S1 C1 178.51(12)
C4 C5 S1 C1 -57.69(13)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 21200374 ChemSpider
