#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006989.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2006989
loop_
_publ_author_name
'Brigas, A. F.'
'Goncalves, P. M.'
'Johnstone, R. A. W.'
_publ_section_title
;
 Electronic Effects on C---O---C Ether Bonds in 3-Aryloxy Derivatives
 of Benzisothiazole 1,1-Dioxides: Rapid Ethanolysis of
 3-(4-Nitrophenoxy)-1,2-benzisothiazole 1,1-Dioxide, (1), to give
 3-Ethoxy-1,2-benzisothiazole 1,1-Dioxide, (2)
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              251
_journal_page_last               253
_journal_volume                  54
_journal_year                    1998
_chemical_formula_sum            'C13 H8 N2 O5 S'
_chemical_formula_weight         304.27
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.803(3)
_cell_length_b                   10.780(16)
_cell_length_c                   17.272(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.1
_cell_measurement_theta_min      10.2
_cell_volume                     2570(4)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
; MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1995)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1995)'
_computing_molecular_graphics    TEXSAN
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    TEXSAN
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.881
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measurement_device_type  Rigaku_AFC6S
_diffrn_measurement_method       \w-2\q
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0526
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2256
_diffrn_reflns_theta_full        24.95
_diffrn_reflns_theta_max         24.95
_diffrn_reflns_theta_min         2.67
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    none
_exptl_crystal_description       prism
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.30
_refine_ls_extinction_coef       0.0024(4)
_refine_ls_extinction_method     SHELXL97_(Sheldrick,_1997)
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    H_atom_treatment_mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2256
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.033P)^2^+1.37P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_ref         0.1067
_reflns_number_gt                1552
_reflns_number_total             2256
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    bm1162.cif
_[local]_cod_data_source_block   1
_cod_database_code               2006989
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'
'-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_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
S1 0.52650(5) 0.21015(6) 0.73380(4) 0.0435(2) Uani d . 1 S
O1 0.41094(12) 0.44681(17) 0.60862(12) 0.0488(5) Uani d . 1 O
O2 0.53909(15) 0.08836(18) 0.70403(14) 0.0632(6) Uani d . 1 O
O3 0.51374(16) 0.2236(2) 0.81516(12) 0.0666(7) Uani d . 1 O
O4 -0.03669(15) 0.4079(2) 0.55661(14) 0.0736(7) Uani d . 1 O
O5 0.01157(16) 0.2405(3) 0.50069(17) 0.0878(9) Uani d . 1 O
N1 0.43390(14) 0.2773(2) 0.68860(13) 0.0398(6) Uani d . 1 N
N2 0.02688(17) 0.3363(3) 0.53655(15) 0.0552(7) Uani d . 1 N
C1 0.46596(18) 0.3711(2) 0.65113(15) 0.0381(6) Uani d . 1 C
C2 0.31329(18) 0.4132(2) 0.59441(16) 0.0401(6) Uani d . 1 C
C3 0.2430(2) 0.4922(3) 0.61995(16) 0.0474(7) Uani d . 1 C
H3 0.2589 0.5614 0.6494 0.057 Uiso calc R 1 H
C4 0.1474(2) 0.4674(3) 0.60114(17) 0.0503(8) Uani d . 1 C
H4 0.0979 0.5197 0.6174 0.060 Uiso calc R 1 H
C5 0.12772(17) 0.3643(3) 0.55814(15) 0.0414(7) Uani d . 1 C
C6 0.19840(19) 0.2848(3) 0.53293(17) 0.0477(7) Uani d . 1 C
H6 0.1824 0.2153 0.5037 0.057 Uiso calc R 1 H
C7 0.29314(19) 0.3094(3) 0.55146(18) 0.0489(7) Uani d . 1 C
H7 0.3426 0.2569 0.5352 0.059 Uiso calc R 1 H
C8 0.57057(18) 0.3995(2) 0.65326(15) 0.0374(6) Uani d . 1 C
C9 0.61663(18) 0.3115(2) 0.69822(16) 0.0395(6) Uani d . 1 C
C10 0.71574(19) 0.3101(3) 0.70825(17) 0.0491(8) Uani d . 1 C
H10 0.7459 0.2502 0.7385 0.059 Uiso calc R 1 H
C11 0.7681(2) 0.4017(3) 0.67131(18) 0.0552(8) Uani d . 1 C
H11 0.8351 0.4038 0.6769 0.066 Uiso calc R 1 H
C12 0.7232(2) 0.4898(3) 0.62644(18) 0.0566(8) Uani d . 1 C
H12 0.7605 0.5501 0.6020 0.068 Uiso calc R 1 H
C13 0.6227(2) 0.4908(3) 0.61663(17) 0.0490(7) Uani d . 1 C
H13 0.5923 0.5509 0.5865 0.059 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0358(4) 0.0441(4) 0.0505(4) -0.0060(3) -0.0068(3) 0.0019(3)
O1 0.0276(10) 0.0452(11) 0.0736(14) -0.0042(9) -0.0078(9) 0.0106(10)
O2 0.0524(13) 0.0428(12) 0.0944(17) 0.0008(10) -0.0140(12) -0.0063(11)
O3 0.0708(15) 0.0871(17) 0.0418(12) -0.0219(13) -0.0060(11) 0.0092(11)
O4 0.0301(11) 0.1029(19) 0.0879(17) 0.0121(12) 0.0016(12) 0.0110(15)
O5 0.0437(13) 0.136(2) 0.0837(17) -0.0155(15) -0.0096(12) -0.0437(18)
N1 0.0292(11) 0.0431(13) 0.0471(14) -0.0036(10) 0.0009(10) -0.0007(11)
N2 0.0269(12) 0.091(2) 0.0479(15) 0.0002(14) -0.0011(11) 0.0046(15)
C1 0.0290(13) 0.0401(15) 0.0454(16) 0.0022(13) -0.0004(12) -0.0061(13)
C2 0.0263(13) 0.0431(16) 0.0509(16) -0.0003(12) -0.0029(12) 0.0094(14)
C3 0.0395(15) 0.0458(17) 0.0570(17) 0.0036(14) -0.0043(14) -0.0063(15)
C4 0.0331(16) 0.062(2) 0.0562(19) 0.0141(14) 0.0011(13) -0.0020(16)
C5 0.0247(13) 0.0600(18) 0.0395(15) -0.0005(13) -0.0005(12) 0.0077(14)
C6 0.0359(15) 0.0519(18) 0.0552(18) -0.0012(13) -0.0012(13) -0.0073(15)
C7 0.0297(14) 0.0481(18) 0.069(2) 0.0054(13) 0.0038(14) -0.0064(15)
C8 0.0254(13) 0.0450(16) 0.0419(16) -0.0030(12) 0.0011(11) -0.0084(13)
C9 0.0313(14) 0.0441(16) 0.0430(15) -0.0029(12) -0.0035(12) -0.0062(13)
C10 0.0328(14) 0.0602(19) 0.0542(18) -0.0010(13) -0.0102(13) -0.0006(15)
C11 0.0283(15) 0.075(2) 0.0620(19) -0.0081(15) -0.0041(14) -0.0043(18)
C12 0.0385(17) 0.067(2) 0.064(2) -0.0180(16) 0.0049(15) 0.0053(18)
C13 0.0374(15) 0.0515(18) 0.0580(19) -0.0074(14) -0.0003(13) 0.0051(15)
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_publ_flag
O2 S1 O3 117.80(15) ?
O2 S1 N1 109.05(13) ?
O3 S1 N1 108.90(13) ?
O2 S1 C9 111.07(15) ?
O3 S1 C9 111.57(13) ?
N1 S1 C9 96.24(13) y
C1 O1 C2 118.7(2) y
C1 N1 S1 108.40(18) y
O4 N2 O5 123.7(3) ?
O4 N2 C5 118.6(3) ?
O5 N2 C5 117.7(3) ?
N1 C1 O1 124.4(2) y
N1 C1 C8 119.3(2) y
O1 C1 C8 116.3(2) y
C3 C2 C7 122.7(3) y
C3 C2 O1 117.5(3) y
C7 C2 O1 119.7(2) y
C2 C3 C4 118.8(3) ?
C5 C4 C3 118.4(3) ?
C4 C5 C6 122.7(3) ?
C4 C5 N2 119.6(3) ?
C6 C5 N2 117.7(3) ?
C5 C6 C7 118.9(3) ?
C2 C7 C6 118.5(3) ?
C13 C8 C9 120.7(2) ?
C13 C8 C1 130.5(3) ?
C9 C8 C1 108.8(2) y
C10 C9 C8 122.3(3) ?
C10 C9 S1 130.4(2) ?
C8 C9 S1 107.24(19) y
C9 C10 C11 117.0(3) ?
C12 C11 C10 121.3(3) ?
C11 C12 C13 121.4(3) ?
C8 C13 C12 117.3(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O2 1.421(3) ?
S1 O3 1.424(2) ?
S1 N1 1.664(2) y
S1 C9 1.766(3) y
O1 C1 1.335(3) y
O1 C2 1.417(3) y
O4 N2 1.219(3) ?
O5 N2 1.223(4) ?
N1 C1 1.279(3) y
N2 C5 1.472(3) ?
C1 C8 1.477(3) y
C2 C3 1.364(4) y
C2 C7 1.371(4) y
C3 C4 1.384(4) ?
C4 C5 1.364(4) ?
C5 C6 1.370(4) ?
C6 C7 1.372(4) ?
C8 C13 1.373(4) ?
C8 C9 1.381(4) y
C9 C10 1.379(3) ?
C10 C11 1.380(4) ?
C11 C12 1.374(4) ?
C12 C13 1.398(4) ?
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
O2 S1 N1 C1 -116.6(2)
O3 S1 N1 C1 113.6(2)
C9 S1 N1 C1 -1.8(2)
S1 N1 C1 O1 -179.6(2)
S1 N1 C1 C8 1.0(3)
C2 O1 C1 N1 -9.4(4)
C2 O1 C1 C8 170.1(2)
C1 O1 C2 C3 119.8(3)
C1 O1 C2 C7 -64.9(3)
C7 C2 C3 C4 -0.7(4)
O1 C2 C3 C4 174.5(2)
C2 C3 C4 C5 0.4(4)
C3 C4 C5 C6 0.0(4)
C3 C4 C5 N2 -179.3(3)
O4 N2 C5 C4 1.4(4)
O5 N2 C5 C4 -177.1(3)
O4 N2 C5 C6 -178.0(3)
O5 N2 C5 C6 3.6(4)
C4 C5 C6 C7 -0.1(4)
N2 C5 C6 C7 179.3(3)
C3 C2 C7 C6 0.6(5)
O1 C2 C7 C6 -174.5(3)
C5 C6 C7 C2 -0.2(4)
N1 C1 C8 C13 177.6(3)
O1 C1 C8 C13 -1.9(4)
N1 C1 C8 C9 0.6(3)
O1 C1 C8 C9 -178.9(2)
C13 C8 C9 C10 -0.4(4)
C1 C8 C9 C10 177.0(3)
C13 C8 C9 S1 -179.1(2)
C1 C8 C9 S1 -1.8(3)
O2 S1 C9 C10 -63.3(3)
O3 S1 C9 C10 70.3(3)
N1 S1 C9 C10 -176.5(3)
O2 S1 C9 C8 115.3(2)
O3 S1 C9 C8 -111.1(2)
N1 S1 C9 C8 2.1(2)
C8 C9 C10 C11 0.2(4)
S1 C9 C10 C11 178.7(2)
C9 C10 C11 C12 -0.2(5)
C10 C11 C12 C13 0.3(5)
C9 C8 C13 C12 0.5(4)
C1 C8 C13 C12 -176.2(3)
C11 C12 C13 C8 -0.5(5)