#------------------------------------------------------------------------------
#$Date: 2016-02-16 02:10:39 +0100 (mar 16 de feb de 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/38/7203892.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_7203892
loop_
_publ_author_name
'Sohár, Pál'
'Forró, Enik'
'Lázár, László'
'Bernáth, Gábor'
'Sillanpää, Reijo'
'Fülöp, Ferenc'
_publ_section_title
;
 Synthesis and stereochemistry of stereoisomeric
 1,2,3-oxathiazino[4,3-a]isoquinolines
;
_journal_issue                   2
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              287
_journal_paper_doi               10.1039/a907236e
_journal_year                    2000
_chemical_formula_moiety         'C14 H19 N O4 S '
_chemical_formula_sum            'C14 H19 N O4 S'
_chemical_formula_weight         297.37
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                105.084(6)
_cell_angle_beta                 92.260(7)
_cell_angle_gamma                104.576(7)
_cell_formula_units_Z            2
_cell_length_a                   8.3082(7)
_cell_length_b                   12.308(1)
_cell_length_c                   7.5713(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296.2
_cell_measurement_theta_max      23.4
_cell_measurement_theta_min      21.2
_cell_volume                     718.91(10)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan for Windows (MSC, 1997)'
_computing_publication_material  'teXsan for Windows (MSC, 1997)'
_computing_structure_refinement  'teXsan for Windows (MSC, 1997)'
_computing_structure_solution
;
SAPI91 (Fan, 1991)
;
_diffrn_ambient_temperature      296.2
_diffrn_measurement_device       'Rigaku AFC5S'
_diffrn_measurement_method       ω-2θ
_diffrn_orient_matrix_UB_11      -0.07736
_diffrn_orient_matrix_UB_12      0.04655
_diffrn_orient_matrix_UB_13      -0.02298
_diffrn_orient_matrix_UB_21      0.08428
_diffrn_orient_matrix_UB_22      0.07366
_diffrn_orient_matrix_UB_23      0.07139
_diffrn_orient_matrix_UB_31      0.05076
_diffrn_orient_matrix_UB_32      0.00716
_diffrn_orient_matrix_UB_33      -0.11544
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.00800
_diffrn_reflns_av_sigmaI/netI    0.035
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            2698
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         24.96
_diffrn_reflns_theta_min         1.78
_diffrn_standards_decay_%        -0.97
_diffrn_standards_interval_count 0
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             316.00
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.809
_refine_ls_goodness_of_fit_ref   1.810
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2052
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.0100
_refine_ls_shift/su_mean         0.0009
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00022|Fo|²]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.0435
_refine_ls_wR_factor_ref         0.0430
_reflns_number_gt                2052
_reflns_number_total             2509
_reflns_threshold_expression     I>3.00σ(I)
_cod_data_source_file            a907236e.txt
_cod_data_source_block           '_18'
_cod_original_cell_volume        718.9(1)
_cod_original_formula_sum        'C14 H19 N O4 S '
_cod_database_code               7203892
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
'   -x,   -y,   -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
S(4) 0.67576(5) 0.31666(3) 0.15549(5) 0.0439(1) 1.000 Uani d ?
O(1) 0.0751(1) 0.01801(8) 0.8082(1) 0.0439(3) 1.000 Uani d ?
O(2) 0.1378(1) 0.24232(8) 0.9279(1) 0.0459(3) 1.000 Uani d ?
O(3) 0.8223(1) 0.39525(9) 0.3201(1) 0.0479(3) 1.000 Uani d ?
O(4) 0.5860(2) 0.3960(1) 0.1117(2) 0.0610(4) 1.000 Uani d ?
N(5) 0.5630(1) 0.23565(9) 0.2781(1) 0.0344(3) 1.000 Uani d ?
C(1) 0.6535(2) 0.3819(1) 0.5762(2) 0.0418(4) 1.000 Uani d ?
C(2) 0.7646(2) 0.4629(1) 0.4822(2) 0.0485(5) 1.000 Uani d ?
C(6) 0.4321(2) 0.1351(1) 0.1590(2) 0.0383(4) 1.000 Uani d ?
C(7) 0.3822(2) 0.0454(1) 0.2652(2) 0.0388(4) 1.000 Uani d ?
C(7A) 0.3320(2) 0.1009(1) 0.4497(2) 0.0320(3) 1.000 Uani d ?
C(8) 0.2299(2) 0.0309(1) 0.5436(2) 0.0349(4) 1.000 Uani d ?
C(9) 0.1718(2) 0.0794(1) 0.7055(2) 0.0344(3) 1.000 Uani d ?
C(10) 0.2103(2) 0.2017(1) 0.7736(2) 0.0334(3) 1.000 Uani d ?
C(11) 0.3153(2) 0.2710(1) 0.6859(2) 0.0344(4) 1.000 Uani d ?
C(11A) 0.3799(2) 0.2215(1) 0.5249(2) 0.0312(3) 1.000 Uani d ?
C(11B) 0.5007(2) 0.3030(1) 0.4400(2) 0.0322(4) 1.000 Uani d ?
C(12) 0.7494(2) 0.3138(2) 0.6587(2) 0.0574(5) 1.000 Uani d ?
C(13) 0.0554(2) -0.1051(1) 0.7610(2) 0.0476(4) 1.000 Uani d ?
C(14) 0.1668(2) 0.3652(1) 0.9969(2) 0.0512(4) 1.000 Uani d ?
H(1) 0.614(2) 0.429(1) 0.666(2) 0.050 1.000 Uiso d ?
H(2) 0.700(2) 0.514(1) 0.442(2) 0.058 1.000 Uiso d ?
H(3) 0.871(2) 0.510(1) 0.564(2) 0.058 1.000 Uiso d ?
H(4) 0.480(2) 0.104(1) 0.045(2) 0.046 1.000 Uiso d ?
H(5) 0.339(2) 0.164(1) 0.127(2) 0.046 1.000 Uiso d ?
H(6) 0.285(2) -0.018(1) 0.194(2) 0.047 1.000 Uiso d ?
H(7) 0.477(2) 0.012(1) 0.280(2) 0.047 1.000 Uiso d ?
H(8) 0.196(2) -0.054(1) 0.489(2) 0.042 1.000 Uiso d ?
H(9) 0.349(2) 0.356(1) 0.738(2) 0.041 1.000 Uiso d ?
H(11B) 0.442(2) 0.353(1) 0.397(2) 0.039 1.000 Uiso d ?
H(11) 0.6756 0.2643 0.7157 0.069 1.000 Uiso c ?
H(12) 0.7957 0.2676 0.5643 0.069 1.000 Uiso c ?
H(13) 0.8368 0.3666 0.7479 0.069 1.000 Uiso c ?
H(14) -0.0142 -0.1380 0.8410 0.057 1.000 Uiso c ?
H(15) 0.0053 -0.1398 0.6374 0.057 1.000 Uiso c ?
H(16) 0.1618 -0.1194 0.7732 0.057 1.000 Uiso c ?
H(17) 0.2834 0.4008 1.0287 0.061 1.000 Uiso c ?
H(18) 0.1261 0.3947 0.9052 0.061 1.000 Uiso c ?
H(19) 0.1101 0.3824 1.1029 0.061 1.000 Uiso c ?
loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0 28 0.002 0.002
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
H 0 38 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
N 0 2 0.004 0.003
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
O 0 8 0.008 0.006
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
S 0 2 0.110 0.124
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-2 3 -1
1 2 -2
-1 3 -2
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S4 O4 106.53(9) . . . ?
O3 S4 N5 96.80(7) . . . ?
O4 S4 N5 110.22(9) . . . ?
C9 O1 C13 117.2(1) . . . ?
C10 O2 C14 117.4(1) . . . ?
S4 O3 C2 114.9(1) . . . ?
S4 N5 C6 111.8(1) . . . ?
S4 N5 C11B 114.8(1) . . . ?
C6 N5 C11B 113.6(1) . . . ?
C2 C1 C11B 109.3(2) . . . ?
C2 C1 C12 112.1(2) . . . ?
C2 C1 H1 106(1) . . . no
C11B C1 C12 113.1(2) . . . ?
C11B C1 H1 107(1) . . . no
C12 C1 H1 110(1) . . . no
O3 C2 C1 110.6(2) . . . ?
O3 C2 H2 109(1) . . . no
O3 C2 H3 104(1) . . . no
C1 C2 H2 110(1) . . . no
C1 C2 H3 111(1) . . . no
H2 C2 H3 112(2) . . . no
N5 C6 C7 107.7(2) . . . ?
N5 C6 H4 108(1) . . . no
N5 C6 H5 108(1) . . . no
C7 C6 H4 112(1) . . . no
C7 C6 H5 113(1) . . . no
H4 C6 H5 109(2) . . . no
C6 C7 C7A 110.2(2) . . . ?
C6 C7 H6 109(1) . . . no
C6 C7 H7 109(1) . . . no
C7A C7 H6 108(1) . . . no
C7A C7 H7 111(1) . . . no
H6 C7 H7 109(2) . . . no
C7 C7A C8 120.0(2) . . . ?
C7 C7A C11A 120.8(2) . . . ?
C8 C7A C11A 119.1(2) . . . ?
C7A C8 C9 121.4(2) . . . ?
C7A C8 H8 119(1) . . . no
C9 C8 H8 120(1) . . . no
O1 C9 C8 125.4(2) . . . ?
O1 C9 C10 115.4(2) . . . ?
C8 C9 C10 119.2(2) . . . ?
O2 C10 C9 115.3(1) . . . ?
O2 C10 C11 125.1(2) . . . ?
C9 C10 C11 119.6(2) . . . ?
C10 C11 C11A 121.1(2) . . . ?
C10 C11 H9 120(1) . . . no
C11A C11 H9 119(1) . . . no
C7A C11A C11 119.3(2) . . . ?
C7A C11A C11B 122.5(1) . . . ?
C11 C11A C11B 118.1(2) . . . ?
N5 C11B C1 107.9(1) . . . ?
N5 C11B C11A 110.7(1) . . . ?
N5 C11B H11B 108(1) . . . no
C1 C11B C11A 112.8(1) . . . ?
C1 C11B H11B 109(1) . . . no
C11A C11B H11B 109(1) . . . no
C1 C12 H11 109.5 . . . no
C1 C12 H12 109.5 . . . no
C1 C12 H13 109.5 . . . no
H11 C12 H12 109.5 . . . no
H11 C12 H13 109.5 . . . no
H12 C12 H13 109.5 . . . no
O1 C13 H14 109.5 . . . no
O1 C13 H15 109.5 . . . no
O1 C13 H16 109.5 . . . no
H14 C13 H15 109.5 . . . no
H14 C13 H16 109.5 . . . no
H15 C13 H16 109.5 . . . no
O2 C14 H17 109.5 . . . no
O2 C14 H18 109.5 . . . no
O2 C14 H19 109.5 . . . no
H17 C14 H18 109.5 . . . no
H17 C14 H19 109.5 . . . no
H18 C14 H19 109.5 . . . no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S4 O3 1.622(1) . . ?
S4 O4 1.462(2) . . ?
S4 N5 1.677(2) . . ?
O1 C9 1.368(2) . . ?
O1 C13 1.428(2) . . ?
O2 C10 1.371(2) . . ?
O2 C14 1.419(2) . . ?
O3 C2 1.464(2) . . ?
N5 C6 1.481(2) . . ?
N5 C11B 1.482(2) . . ?
C1 C2 1.520(3) . . ?
C1 C11B 1.540(3) . . ?
C1 C12 1.516(3) . . ?
C1 H1 0.90(2) . . no
C2 H2 1.02(2) . . no
C2 H3 1.00(2) . . no
C6 C7 1.515(3) . . ?
C6 H4 0.99(2) . . no
C6 H5 0.97(2) . . no
C7 C7A 1.512(2) . . ?
C7 H6 0.99(2) . . no
C7 H7 1.00(2) . . no
C7A C8 1.402(2) . . ?
C7A C11A 1.390(2) . . ?
C8 C9 1.379(2) . . ?
C8 H8 0.98(2) . . no
C9 C10 1.405(2) . . ?
C10 C11 1.377(2) . . ?
C11 C11A 1.405(2) . . ?
C11 H9 0.98(2) . . no
C11A C11B 1.519(2) . . ?
C11B H11B 0.98(2) . . no
C12 H11 0.95 . . no
C12 H12 0.95 . . no
C12 H13 0.95 . . no
C13 H14 0.95 . . no
C13 H15 0.95 . . no
C13 H16 0.95 . . no
C14 H17 0.95 . . no
C14 H18 0.95 . . no
C14 H19 0.95 . . no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
? ? ? ? ? ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
S4 O3 C2 C1 . . . . 65.2(2) no
S4 N5 C6 C7 . . . . 159.5(1) no
S4 N5 C11B C1 . . . . -64.5(2) no
S4 N5 C11B C11A . . . . 171.7(1) no
O1 C9 C8 C7A . . . . -178.4(2) no
O1 C9 C10 O2 . . . . -3.5(2) no
O1 C9 C10 C11 . . . . 176.1(2) no
O2 C10 C9 C8 . . . . 175.6(2) no
O2 C10 C11 C11A . . . . -178.1(2) no
O3 S4 N5 C6 . . . . -168.6(1) no
O3 S4 N5 C11B . . . . 60.1(1) no
O3 C2 C1 C11B . . . . -59.8(2) no
O3 C2 C1 C12 . . . . 66.5(2) no
O4 S4 O3 C2 . . . . 54.4(2) no
O4 S4 N5 C6 . . . . 81.0(1) no
O4 S4 N5 C11B . . . . -50.4(1) no
N5 S4 O3 C2 . . . . -59.1(1) no
N5 C6 C7 C7A . . . . 54.1(2) no
N5 C11B C1 C2 . . . . 59.1(2) no
N5 C11B C1 C12 . . . . -66.6(2) no
N5 C11B C11A C7A . . . . -3.0(2) no
N5 C11B C11A C11 . . . . 176.8(2) no
C1 C11B N5 C6 . . . . 165.0(2) no
C1 C11B C11A C7A . . . . -124.0(2) no
C1 C11B C11A C11 . . . . 55.8(2) no
C2 C1 C11B C11A . . . . -178.3(2) no
C6 N5 C11B C11A . . . . 41.2(2) no
C6 C7 C7A C8 . . . . 158.4(2) no
C6 C7 C7A C11A . . . . -18.9(2) no
C7 C6 N5 C11B . . . . -68.6(2) no
C7 C7A C8 C9 . . . . -175.2(2) no
C7 C7A C11A C11 . . . . 172.7(2) no
C7 C7A C11A C11B . . . . -7.5(3) no
C7A C8 C9 C10 . . . . 2.7(3) no
C7A C11A C11 C10 . . . . 2.3(3) no
C8 C7A C11A C11 . . . . -4.5(3) no
C8 C7A C11A C11B . . . . 175.3(2) no
C8 C9 O1 C13 . . . . 10.8(3) no
C8 C9 C10 C11 . . . . -4.9(3) no
C9 C8 C7A C11A . . . . 2.1(3) no
C9 C10 O2 C14 . . . . -177.2(2) no
C9 C10 C11 C11A . . . . 2.4(3) no
C10 C9 O1 C13 . . . . -170.2(2) no
C10 C11 C11A C11B . . . . -177.5(2) no
C11 C10 O2 C14 . . . . 3.3(3) no
C11A C11B C1 C12 . . . . 56.0(2) no
