##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2005-06-15
_journal_date_accepted     2005-07-07
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue      8
_journal_page_first     o2518
_journal_page_last     o2519
_journal_paper_category     EO
_journal_coeditor_code     LH6452
_publ_contact_author_name     'Li Tian'
_publ_contact_author_address
;
College of Chemistry and Life
Tianjin Normal University
Tianjin 300074
P.R.China
;
_publ_contact_author_email     tian_lili@eyou.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     '8622 24713137'
_publ_section_title
;
5-Azido-3,3-dimethyl-2-oxo-1-thia-4,6-diazaindan 1,1-dioxide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Li Tian' .
;
College of Chemistry and Life Sciences
Tianjin Normal University
Tianjin 300074
People's Republic of China
;
    'Da-Xiang Wang' .
;
China Automotive Technology and Research Center
PO Box 59
Tianjin 300162
People's Republic of China
;
data_3
_chemical_name_systematic
;
5-Azido-3,3-dimethyl-2-oxo-1-thia-4,6-diazaindan 1,1-dioxide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C7 H7 N5 O3 S'
_chemical_formula_sum     'C7 H7 N5 O3 S'
_chemical_formula_iupac     'C7 H7 N5 O3 S'
_chemical_formula_weight     241.24
_chemical_melting_point     161
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     14.4162(16)
_cell_length_b     8.5691(10)
_cell_length_c     17.0016(19)
_cell_angle_alpha     90.00
_cell_angle_beta     105.3650(10)
_cell_angle_gamma     90.00
_cell_volume     2025.2(4)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     3013
_cell_measurement_theta_min     2.48
_cell_measurement_theta_max     27.78
_cell_measurement_temperature     293(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.22
_exptl_crystal_size_mid     0.16
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.582
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     992
_exptl_absorpt_coefficient_mu     0.321
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9328
_exptl_absorpt_correction_T_max     0.9686
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEX-II CCD'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5286
_diffrn_reflns_av_R_equivalents     0.0154
_diffrn_reflns_av_sigmaI/netI     0.0162
_diffrn_reflns_theta_min     2.79
_diffrn_reflns_theta_max     25.02
_diffrn_reflns_theta_full     25.02
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     20
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     1784
_reflns_number_gt     1587
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0336
_refine_ls_R_factor_gt     0.0297
_refine_ls_wR_factor_gt     0.0838
_refine_ls_wR_factor_ref     0.0871
_refine_ls_goodness_of_fit_ref     1.060
_refine_ls_restrained_S_all     1.060
_refine_ls_number_reflns     1784
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0468P)²+1.3512P] where P = (Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.289
_refine_diff_density_min     -0.258
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.0045(5)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection     'APEXII (Bruker, 1998)'
_computing_cell_refinement     'SAINT (Bruker, 1999)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1999)'
_computing_publication_material     'SHELXTL'
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_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    S1 0.17681(3) 0.18013(5) 0.19388(2) 0.03951(18) Uani d . 1 . . S
    O1 0.17061(10) 0.05324(17) 0.13946(8) 0.0585(4) Uani d . 1 . . O
    O2 0.15377(10) 0.33066(16) 0.15990(8) 0.0576(4) Uani d . 1 . . O
    O3 0.11307(9) 0.13929(18) 0.25320(7) 0.0536(4) Uani d . 1 . . O
    N1 0.44807(10) 0.19697(16) 0.33826(8) 0.0389(3) Uani d . 1 . . N
    N2 0.33040(10) 0.18719(16) 0.41569(8) 0.0385(3) Uani d . 1 . . N
    N3 0.49018(11) 0.1923(2) 0.48175(9) 0.0519(4) Uani d . 1 . . N
    N4 0.57431(11) 0.18141(18) 0.47431(9) 0.0467(4) Uani d . 1 . . N
    N5 0.65144(12) 0.1704(2) 0.47631(11) 0.0633(5) Uani d . 1 . . N
    C1 0.13207(14) 0.0420(2) 0.38901(13) 0.0555(5) Uani d . 1 . . C
    H1A 0.0634 0.0326 0.3772 0.083 Uiso calc R 1 . . H
    H1B 0.1583 0.0611 0.4462 0.083 Uiso calc R 1 . . H
    H1C 0.1585 -0.0529 0.3742 0.083 Uiso calc R 1 . . H
    C2 0.12069(13) 0.3315(2) 0.36141(13) 0.0517(5) Uani d . 1 . . C
    H2A 0.1351 0.4105 0.3264 0.078 Uiso calc R 1 . . H
    H2B 0.1513 0.3572 0.4172 0.078 Uiso calc R 1 . . H
    H2C 0.0524 0.3259 0.3537 0.078 Uiso calc R 1 . . H
    C3 0.15726(12) 0.1760(2) 0.34090(10) 0.0394(4) Uani d . 1 . . C
    C4 0.26360(11) 0.18306(18) 0.34584(10) 0.0343(4) Uani d . 1 . . C
    C5 0.42007(11) 0.19209(19) 0.40737(10) 0.0373(4) Uani d . 1 . . C
    C6 0.37854(12) 0.19444(19) 0.26910(10) 0.0384(4) Uani d . 1 . . C
    H6 0.3939 0.1986 0.2194 0.046 Uiso calc R 1 . . H
    C7 0.28357(11) 0.18562(18) 0.27084(9) 0.0351(4) Uani d . 1 . . C
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 0.0348(3) 0.0491(3) 0.0326(3) 0.00002(17) 0.00519(17) -0.00238(17)
    O1 0.0574(8) 0.0642(9) 0.0500(7) -0.0023(7) 0.0072(6) -0.0183(7)
    O2 0.0561(8) 0.0560(9) 0.0517(8) 0.0054(6) -0.0016(6) 0.0094(6)
    O3 0.0336(6) 0.0850(10) 0.0410(7) -0.0097(6) 0.0078(5) -0.0049(7)
    N1 0.0323(7) 0.0502(8) 0.0352(7) -0.0008(6) 0.0108(6) 0.0015(6)
    N2 0.0341(7) 0.0498(8) 0.0327(7) 0.0000(6) 0.0109(6) 0.0019(6)
    N3 0.0337(8) 0.0850(12) 0.0357(8) -0.0001(7) 0.0067(6) 0.0012(7)
    N4 0.0387(9) 0.0620(10) 0.0360(8) -0.0034(7) 0.0036(6) 0.0017(7)
    N5 0.0356(9) 0.0890(14) 0.0616(11) -0.0023(8) 0.0061(8) 0.0008(9)
    C1 0.0488(10) 0.0583(12) 0.0636(12) -0.0085(9) 0.0222(9) 0.0086(10)
    C2 0.0430(10) 0.0572(12) 0.0599(12) 0.0065(8) 0.0221(9) 0.0017(9)
    C3 0.0319(8) 0.0520(10) 0.0350(8) -0.0029(7) 0.0100(7) -0.0004(7)
    C4 0.0332(8) 0.0368(8) 0.0344(8) 0.0007(6) 0.0115(6) 0.0011(6)
    C5 0.0341(8) 0.0445(9) 0.0330(8) -0.0004(7) 0.0082(7) 0.0018(7)
    C6 0.0368(8) 0.0478(10) 0.0332(8) 0.0002(7) 0.0136(7) 0.0014(7)
    C7 0.0340(8) 0.0405(9) 0.0305(8) -0.0001(6) 0.0080(6) 0.0008(6)
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O1 . 1.4151(14) ?
    S1 O2 . 1.4165(14) ?
    S1 O3 . 1.5732(13) ?
    S1 C7 . 1.7366(16) ?
    O3 C3 . 1.492(2) ?
    N1 C6 . 1.328(2) yes
    N1 C5 . 1.340(2) yes
    N2 C4 . 1.316(2) yes
    N2 C5 . 1.338(2) yes
    N3 N4 . 1.256(2) yes
    N3 C5 . 1.394(2) yes
    N4 N5 . 1.107(2) yes
    C1 C3 . 1.509(2) ?
    C1 H1A . 0.9600 ?
    C1 H1B . 0.9600 ?
    C1 H1C . 0.9600 ?
    C2 C3 . 1.508(2) ?
    C2 H2A . 0.9600 ?
    C2 H2B . 0.9600 ?
    C2 H2C . 0.9600 ?
    C3 C4 . 1.514(2) yes
    C4 C7 . 1.380(2) yes
    C6 C7 . 1.379(2) yes
    C6 H6 . 0.9300 yes
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 S1 O2 . . 117.75(9) ?
    O1 S1 O3 . . 107.57(8) ?
    O2 S1 O3 . . 110.51(9) ?
    O1 S1 C7 . . 113.78(8) ?
    O2 S1 C7 . . 110.36(8) ?
    O3 S1 C7 . . 94.28(7) ?
    C3 O3 S1 . . 115.25(10) ?
    C6 N1 C5 . . 116.35(14) yes
    C4 N2 C5 . . 113.70(13) yes
    N4 N3 C5 . . 113.33(14) yes
    N5 N4 N3 . . 172.71(19) yes
    C3 C1 H1A . . 109.5 ?
    C3 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    C3 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    C3 C2 H2A . . 109.5 ?
    C3 C2 H2B . . 109.5 ?
    H2A C2 H2B . . 109.5 ?
    C3 C2 H2C . . 109.5 ?
    H2A C2 H2C . . 109.5 ?
    H2B C2 H2C . . 109.5 ?
    O3 C3 C2 . . 109.56(14) ?
    O3 C3 C1 . . 106.31(14) ?
    C2 C3 C1 . . 113.46(15) ?
    O3 C3 C4 . . 102.82(12) ?
    C2 C3 C4 . . 111.28(14) yes
    C1 C3 C4 . . 112.70(14) yes
    N2 C4 C7 . . 123.46(15) yes
    N2 C4 C3 . . 122.62(14) yes
    C7 C4 C3 . . 113.92(14) yes
    N2 C5 N1 . . 128.13(15) yes
    N2 C5 N3 . . 113.13(14) yes
    N1 C5 N3 . . 118.74(14) yes
    N1 C6 C7 . . 120.17(15) yes
    N1 C6 H6 . . 119.9 yes
    C7 C6 H6 . . 119.9 yes
    C6 C7 C4 . . 118.17(15) yes
    C6 C7 S1 . . 132.21(13) yes
    C4 C7 S1 . . 109.61(12) yes
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
    O1 S1 O3 C3 . . . . 136.28(12) ?
    O2 S1 O3 C3 . . . . -93.93(13) ?
    C7 S1 O3 C3 . . . . 19.68(13) ?
    S1 O3 C3 C2 . . . . 97.30(15) ?
    S1 O3 C3 C1 . . . . -139.72(13) ?
    S1 O3 C3 C4 . . . . -21.11(16) ?
    C5 N2 C4 C7 . . . . -0.8(2) ?
    C5 N2 C4 C3 . . . . 179.56(14) ?
    O3 C3 C4 N2 . . . . -168.40(14) ?
    C2 C3 C4 N2 . . . . 74.4(2) ?
    C1 C3 C4 N2 . . . . -54.4(2) ?
    O3 C3 C4 C7 . . . . 11.96(18) ?
    C2 C3 C4 C7 . . . . -105.24(17) ?
    C1 C3 C4 C7 . . . . 126.00(16) ?
    C4 N2 C5 N1 . . . . 1.8(2) ?
    C4 N2 C5 N3 . . . . -178.41(14) ?
    C6 N1 C5 N2 . . . . -1.1(3) ?
    C6 N1 C5 N3 . . . . 179.13(15) ?
    N4 N3 C5 N2 . . . . 173.41(15) ?
    N4 N3 C5 N1 . . . . -6.7(2) ?
    C5 N1 C6 C7 . . . . -0.6(2) ?
    N1 C6 C7 C4 . . . . 1.4(2) ?
    N1 C6 C7 S1 . . . . 179.99(13) ?
    N2 C4 C7 C6 . . . . -0.6(2) ?
    C3 C4 C7 C6 . . . . 179.02(14) ?
    N2 C4 C7 S1 . . . . -179.52(13) ?
    C3 C4 C7 S1 . . . . 0.12(17) ?
    O1 S1 C7 C6 . . . . 58.73(19) ?
    O2 S1 C7 C6 . . . . -76.20(18) ?
    O3 S1 C7 C6 . . . . 170.06(17) ?
    O1 S1 C7 C4 . . . . -122.58(12) ?
    O2 S1 C7 C4 . . . . 102.48(13) ?
    O3 S1 C7 C4 . . . . -11.25(13) ?
