#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006990.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_2006990
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            'C9 H9 N O3 S'
_chemical_formula_weight         211.23
_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'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.15(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.149(4)
_cell_length_b                   8.178(5)
_cell_length_c                   16.556(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      7.4
_cell_measurement_theta_min      3.5
_cell_volume                     966.5(8)
_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 0.927
_diffrn_measured_fraction_theta_max 0.927
_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    0.0631
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            1699
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.78
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.314
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    H_atom_treatment_mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1699
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0441
_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^)+(0.027P)^2^+0.480P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_ref         0.1079
_reflns_number_gt                1133
_reflns_number_total             1699
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    bm1162.cif
_[local]_cod_data_source_block   2
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
_cod_database_code               2006990
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_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 0.25157(12) 0.72651(9) 0.61628(5) 0.0468(3) Uani d . 1 S
O1 0.2763(3) 0.7788(2) 0.39651(12) 0.0465(5) Uani d . 1 O
O2 0.4197(4) 0.6894(3) 0.66264(14) 0.0692(8) Uani d . 1 O
O3 0.0806(4) 0.6666(3) 0.64597(14) 0.0667(7) Uani d . 1 O
N1 0.2698(4) 0.6635(3) 0.52269(15) 0.0445(7) Uani d . 1 N
C1 0.2668(4) 0.7887(4) 0.47522(18) 0.0384(7) Uani d . 1 C
C2 0.2883(5) 0.6136(4) 0.3628(2) 0.0576(9) Uani d . 1 C
H2A 0.1805 0.5493 0.3766 0.069 Uiso calc R 1 H
H2B 0.4007 0.5592 0.3845 0.069 Uiso calc R 1 H
C3 0.2931(7) 0.6302(5) 0.2739(2) 0.0802(13) Uani d . 1 C
H3A 0.3015 0.5237 0.2499 0.120 Uiso calc R 1 H
H3B 0.4001 0.6941 0.2610 0.120 Uiso calc R 1 H
H3C 0.1809 0.6835 0.2531 0.120 Uiso calc R 1 H
C4 0.2508(4) 0.9522(3) 0.51095(17) 0.0358(7) Uani d . 1 C
C5 0.2390(4) 0.9367(3) 0.59378(18) 0.0394(7) Uani d . 1 C
C6 0.2208(5) 1.0692(4) 0.6434(2) 0.0533(9) Uani d . 1 C
H6 0.2126 1.0574 0.6989 0.064 Uiso calc R 1 H
C7 0.2152(5) 1.2217(4) 0.6068(2) 0.0601(9) Uani d . 1 C
H7 0.2026 1.3147 0.6384 0.072 Uiso calc R 1 H
C8 0.2280(5) 1.2380(4) 0.5245(2) 0.0571(9) Uani d . 1 C
H8 0.2243 1.3419 0.5016 0.068 Uiso calc R 1 H
C9 0.2461(4) 1.1038(4) 0.4752(2) 0.0460(8) Uani d . 1 C
H9 0.2548 1.1154 0.4197 0.055 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 0.0642(5) 0.0356(4) 0.0409(4) 0.0034(4) 0.0045(4) 0.0038(4)
O1 0.0608(14) 0.0398(11) 0.0394(12) 0.0049(11) 0.0070(10) -0.0007(10)
O2 0.0848(18) 0.0640(17) 0.0563(15) 0.0232(14) -0.0182(13) 0.0075(12)
O3 0.0854(18) 0.0559(15) 0.0613(16) -0.0154(13) 0.0264(13) 0.0071(12)
N1 0.0606(18) 0.0310(14) 0.0421(16) 0.0029(12) 0.0048(13) 0.0022(12)
C1 0.0362(16) 0.0369(16) 0.0420(17) 0.0013(13) 0.0032(13) 0.0008(14)
C2 0.076(3) 0.044(2) 0.053(2) 0.0083(17) 0.0109(18) -0.0060(16)
C3 0.129(4) 0.066(3) 0.045(2) 0.021(2) 0.005(2) -0.0090(19)
C4 0.0320(16) 0.0325(16) 0.0427(18) 0.0007(12) 0.0010(13) 0.0006(13)
C5 0.0379(17) 0.0341(17) 0.0458(19) 0.0017(13) -0.0003(14) 0.0013(13)
C6 0.067(2) 0.043(2) 0.049(2) 0.0021(16) 0.0010(16) -0.0097(16)
C7 0.070(2) 0.0362(18) 0.073(3) 0.0001(17) -0.0041(19) -0.0138(19)
C8 0.062(2) 0.0339(19) 0.075(2) -0.0012(16) -0.0027(18) 0.0066(18)
C9 0.050(2) 0.0374(18) 0.051(2) 0.0003(15) 0.0030(15) 0.0058(16)
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 117.03(16) ?
O2 S1 N1 109.43(14) ?
O3 S1 N1 109.29(15) ?
O2 S1 C5 110.76(15) ?
O3 S1 C5 111.89(15) ?
N1 S1 C5 96.46(13) y
C1 O1 C2 116.3(2) y
C1 N1 S1 109.0(2) y
N1 C1 O1 123.8(3) y
N1 C1 C4 118.4(3) y
O1 C1 C4 117.8(3) y
O1 C2 C3 107.4(3) y
C9 C4 C5 120.5(3) ?
C9 C4 C1 130.5(3) ?
C5 C4 C1 109.0(3) y
C6 C5 C4 122.3(3) ?
C6 C5 S1 130.6(3) ?
C4 C5 S1 107.1(2) y
C5 C6 C7 116.9(3) ?
C8 C7 C6 121.1(3) y
C9 C8 C7 121.5(3) y
C4 C9 C8 117.8(3) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O2 1.423(2) ?
S1 O3 1.429(2) ?
S1 N1 1.645(3) y
S1 C5 1.760(3) y
O1 C1 1.311(3) y
O1 C2 1.466(4) y
N1 C1 1.291(4) y
C1 C4 1.469(4) y
C2 C3 1.481(5) y
C4 C9 1.373(4) ?
C4 C5 1.384(4) y
C5 C6 1.370(4) ?
C6 C7 1.386(5) ?
C7 C8 1.378(5) ?
C8 C9 1.377(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 -114.9(2)
O3 S1 N1 C1 115.8(2)
C5 S1 N1 C1 -0.1(2)
S1 N1 C1 O1 -179.1(2)
S1 N1 C1 C4 0.6(3)
C2 O1 C1 N1 0.9(4)
C2 O1 C1 C4 -178.8(3)
C1 O1 C2 C3 178.7(3)
N1 C1 C4 C9 179.4(3)
O1 C1 C4 C9 -1.0(5)
N1 C1 C4 C5 -0.8(4)
O1 C1 C4 C5 178.8(2)
C9 C4 C5 C6 0.5(5)
C1 C4 C5 C6 -179.3(3)
C9 C4 C5 S1 -179.5(2)
C1 C4 C5 S1 0.6(3)
O2 S1 C5 C6 -66.8(3)
O3 S1 C5 C6 65.8(3)
N1 S1 C5 C6 179.6(3)
O2 S1 C5 C4 113.3(2)
O3 S1 C5 C4 -114.1(2)
N1 S1 C5 C4 -0.3(2)
C4 C5 C6 C7 -0.2(5)
S1 C5 C6 C7 179.9(3)
C5 C6 C7 C8 -0.2(5)
C6 C7 C8 C9 0.2(5)
C5 C4 C9 C8 -0.5(4)
C1 C4 C9 C8 179.3(3)
C7 C8 C9 C4 0.1(5)