#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/16/2011697.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_2011697
loop_
_publ_author_name
'Parvez, Masood'
'Yadav, Veejendra K.'
'Senthil, Govindaraji'
_publ_section_title
;
 Some Diels--Alder adducts of 6-vinyl-1-oxa-4-thiaspiro[4.5]dec-6-ene
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              82
_journal_page_last               85
_journal_paper_doi               10.1107/S0108270100013597
_journal_volume                  57
_journal_year                    2001
_chemical_formula_moiety         'C13 H17 N3 O3 S'
_chemical_formula_sum            'C13 H17 N3 O3 S'
_chemical_formula_weight         295.36
_chemical_name_common
;
N-Methyl-1,3,4-triazoline-2,5-dione adduct of
1-oxa-4-thia-6-vinyl-spiro[4.5]dec-6-ene
;
_chemical_name_systematic
;
2-methyl-5,7,8,9,10,10a-hexahydro-1H-1,2,4-triazolo[1,2-a]cinnoline-7-spiro-
2'-[1,3]oxathiolane-1,3-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.944(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.258(2)
_cell_length_b                   7.3897(17)
_cell_length_c                   14.2874(13)
_cell_measurement_reflns_used    12
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      10
_cell_volume                     1345.9(4)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,
 1988)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1994)'
_computing_molecular_graphics    TEXSAN
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SAPI91 (Fan, 1991)'
_diffrn_ambient_temperature      170(2)
_diffrn_measurement_device_type  'Rigaku AFC-6S'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     .71069
_diffrn_reflns_av_R_equivalents  .047
_diffrn_reflns_av_sigmaI/netI    .086
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2487
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        <0.1
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .25
_exptl_absorpt_correction_T_max  .93
_exptl_absorpt_correction_T_min  .90
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
via ψ-scan (3 reflections) (North et al., 1968)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          .42
_exptl_crystal_size_mid          .35
_exptl_crystal_size_min          .31
_refine_diff_density_max         .24
_refine_diff_density_min         -.27
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.00
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2380
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.00
_refine_ls_R_factor_all          .113
_refine_ls_R_factor_gt           .042
_refine_ls_shift/su_max          <0.01
_refine_ls_shift/su_mean         .00
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.058P)²+0.264P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .130
_reflns_number_gt                1337
_reflns_number_total             2380
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            da1148.cif
_cod_data_source_block           IIIa
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2011697
_cod_database_fobs_code          2011697
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
S1 .51331(7) .27399(13) .57718(7) .0331(3) Uani d . 1 . . S
O1 .65908(18) .0560(3) .68045(17) .0357(6) Uani d . 1 . . O
O2 1.00119(18) .2512(4) .39467(19) .0434(7) Uani d . 1 . . O
O3 .75030(18) .6868(3) .37666(17) .0344(6) Uani d . 1 . . O
N1 .8668(2) .2852(4) .4679(2) .0273(6) Uani d . 1 . . N
N2 .7777(2) .4016(4) .4459(2) .0266(7) Uani d . 1 . . N
N3 .8899(2) .5003(4) .3698(2) .0304(7) Uani d . 1 . . N
C1 .4744(3) .0719(5) .6291(3) .0409(9) Uani d . 1 . . C
H1A .4122 .0953 .6530 .049 Uiso calc R 1 . . H
H1B .4577 -.0269 .5805 .049 Uiso calc R 1 . . H
C2 .5683(3) .0240(5) .7120(3) .0412(10) Uani d . 1 . . C
H2A .5698 .0996 .7696 .049 Uiso calc R 1 . . H
H2B .5650 -.1047 .7301 .049 Uiso calc R 1 . . H
C3 .6551(2) .2299(5) .6385(2) .0275(8) Uani d . 1 . . C
C4 .6972(3) .3752(5) .7150(2) .0344(9) Uani d . 1 . . C
H4A .6536 .3784 .7612 .041 Uiso calc R 1 . . H
H4B .7697 .3437 .7521 .041 Uiso calc R 1 . . H
C5 .6970(3) .5610(5) .6699(3) .0347(9) Uani d . 1 . . C
H5A .7268 .6504 .7216 .042 Uiso calc R 1 . . H
H5B .6239 .5973 .6372 .042 Uiso calc R 1 . . H
C6 .7610(3) .5610(5) .5960(3) .0343(9) Uani d . 1 . . C
H6A .8357 .5378 .6296 .041 Uiso calc R 1 . . H
H6B .7558 .6810 .5642 .041 Uiso calc R 1 . . H
C7 .7199(2) .4148(4) .5191(2) .0245(8) Uani d . 1 . . C
H7 .6458 .4467 .4844 .029 Uiso calc R 1 . . H
C8 .7180(2) .2321(4) .5654(2) .0227(7) Uani d . 1 . . C
C9 .7730(2) .0919(4) .5494(3) .0272(8) Uani d . 1 . . C
H9 .7663 -.0191 .5806 .033 Uiso calc R 1 . . H
C10 .8447(3) .0973(4) .4854(3) .0280(8) Uani d . 1 . . C
H10A .9108 .0332 .5171 .034 Uiso calc R 1 . . H
H10B .8114 .0363 .4228 .034 Uiso calc R 1 . . H
C11 .9287(3) .3358(5) .4090(2) .0291(8) Uani d . 1 . . C
C12 .7997(3) .5467(5) .3956(2) .0273(8) Uani d . 1 . . C
C13 .9333(3) .6084(6) .3050(3) .0440(10) Uani d . 1 . . C
H13A .9888 .6869 .3437 .066 Uiso calc R 1 . . H
H13B .8777 .6829 .2632 .066 Uiso calc R 1 . . H
H13C .9626 .5282 .2645 .066 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S .1246 .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
C1 S1 C3 91.56(17) y
C3 O1 C2 110.5(3) y
C11 N1 N2 107.3(3) y
C11 N1 C10 123.0(3) y
N2 N1 C10 114.8(2) y
C12 N2 N1 107.8(2) y
C12 N2 C7 123.7(3) y
N1 N2 C7 116.7(2) y
C11 N3 C12 111.3(3) y
C11 N3 C13 125.0(3) y
C12 N3 C13 123.6(3) y
C2 C1 S1 104.5(3) n
C2 C1 H1A 110.9 n
S1 C1 H1A 110.9 n
C2 C1 H1B 110.9 n
S1 C1 H1B 110.9 n
H1A C1 H1B 108.9 n
O1 C2 C1 107.5(3) n
O1 C2 H2A 110.2 n
C1 C2 H2A 110.2 n
O1 C2 H2B 110.2 n
C1 C2 H2B 110.2 n
H2A C2 H2B 108.5 n
O1 C3 C8 109.9(3) n
O1 C3 C4 111.9(3) n
C8 C3 C4 109.1(3) n
O1 C3 S1 105.8(2) n
C8 C3 S1 110.5(2) n
C4 C3 S1 109.6(2) n
C5 C4 C3 112.1(3) n
C5 C4 H4A 109.2 n
C3 C4 H4A 109.2 n
C5 C4 H4B 109.2 n
C3 C4 H4B 109.2 n
H4A C4 H4B 107.9 n
C4 C5 C6 111.0(3) n
C4 C5 H5A 109.4 n
C6 C5 H5A 109.4 n
C4 C5 H5B 109.4 n
C6 C5 H5B 109.4 n
H5A C5 H5B 108.0 n
C5 C6 C7 109.9(3) n
C5 C6 H6A 109.7 n
C7 C6 H6A 109.7 n
C5 C6 H6B 109.7 n
C7 C6 H6B 109.7 n
H6A C6 H6B 108.2 n
N2 C7 C8 109.2(3) n
N2 C7 C6 114.1(3) n
C8 C7 C6 111.4(3) n
N2 C7 H7 107.3 n
C8 C7 H7 107.3 n
C6 C7 H7 107.3 n
C9 C8 C3 123.3(3) n
C9 C8 C7 123.4(3) n
C3 C8 C7 113.1(3) n
C8 C9 C10 124.1(3) n
C8 C9 H9 118.0 n
C10 C9 H9 118.0 n
N1 C10 C9 108.9(3) n
N1 C10 H10A 109.9 n
C9 C10 H10A 109.9 n
N1 C10 H10B 109.9 n
C9 C10 H10B 109.9 n
H10A C10 H10B 108.3 n
O2 C11 N3 127.8(3) n
O2 C11 N1 126.6(3) n
N3 C11 N1 105.6(3) n
O3 C12 N2 127.3(3) n
O3 C12 N3 127.0(3) n
N2 C12 N3 105.7(3) n
N3 C13 H13A 109.5 n
N3 C13 H13B 109.5 n
H13A C13 H13B 109.5 n
N3 C13 H13C 109.5 n
H13A C13 H13C 109.5 n
H13B C13 H13C 109.5 n
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 C1 . 1.805(4) y
S1 C3 . 1.872(3) y
O1 C3 . 1.413(4) y
O1 C2 . 1.417(4) y
O2 C11 . 1.210(4) y
O3 C12 . 1.215(4) y
N1 C11 . 1.379(4) y
N1 N2 . 1.425(4) y
N1 C10 . 1.455(4) y
N2 C12 . 1.366(4) y
N2 C7 . 1.460(4) y
N3 C11 . 1.378(4) y
N3 C12 . 1.388(4) y
N3 C13 . 1.454(4) y
C1 C2 . 1.506(5) n
C1 H1A . .9900 n
C1 H1B . .9900 n
C2 H2A . .9900 n
C2 H2B . .9900 n
C3 C8 . 1.506(4) n
C3 C4 . 1.524(5) n
C4 C5 . 1.516(5) n
C4 H4A . .9900 n
C4 H4B . .9900 n
C5 C6 . 1.525(5) n
C5 H5A . .9900 n
C5 H5B . .9900 n
C6 C7 . 1.530(5) n
C6 H6A . .9900 n
C6 H6B . .9900 n
C7 C8 . 1.506(4) n
C7 H7 . 1.0000 n
C8 C9 . 1.322(4) n
C9 C10 . 1.490(5) n
C9 H9 . .9500 n
C10 H10A . .9900 n
C10 H10B . .9900 n
C13 H13A . .9800 n
C13 H13B . .9800 n
C13 H13C . .9800 n
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
_geom_torsion_publ_flag
C11 N1 N2 C12 -15.9(3) n
C10 N1 N2 C12 -156.6(3) n
C11 N1 N2 C7 -160.3(3) n
C10 N1 N2 C7 59.0(4) n
C3 S1 C1 C2 17.6(3) n
C3 O1 C2 C1 49.5(4) n
S1 C1 C2 O1 -39.9(4) n
C2 O1 C3 C8 -153.0(3) n
C2 O1 C3 C4 85.7(3) n
C2 O1 C3 S1 -33.7(3) n
C1 S1 C3 O1 7.8(2) n
C1 S1 C3 C8 126.7(3) n
C1 S1 C3 C4 -113.1(3) n
O1 C3 C4 C5 177.8(3) n
C8 C3 C4 C5 55.9(4) n
S1 C3 C4 C5 -65.1(3) n
C3 C4 C5 C6 -57.4(4) n
C4 C5 C6 C7 55.5(4) n
C12 N2 C7 C8 -175.3(3) n
N1 N2 C7 C8 -37.1(4) n
C12 N2 C7 C6 -50.0(4) n
N1 N2 C7 C6 88.2(3) n
C5 C6 C7 N2 -178.8(3) n
C5 C6 C7 C8 -54.6(4) n
O1 C3 C8 C9 -3.8(4) n
C4 C3 C8 C9 119.2(3) n
S1 C3 C8 C9 -120.2(3) n
O1 C3 C8 C7 -178.5(2) n
C4 C3 C8 C7 -55.5(3) n
S1 C3 C8 C7 65.1(3) n
N2 C7 C8 C9 8.3(4) n
C6 C7 C8 C9 -118.6(3) n
N2 C7 C8 C3 -177.0(3) n
C6 C7 C8 C3 56.1(3) n
C3 C8 C9 C10 -173.1(3) n
C7 C8 C9 C10 1.1(5) n
C11 N1 C10 C9 -178.1(3) n
N2 N1 C10 C9 -44.3(4) n
C8 C9 C10 N1 16.2(5) n
C12 N3 C11 O2 174.0(4) n
C13 N3 C11 O2 -2.7(6) n
C12 N3 C11 N1 -5.3(4) n
C13 N3 C11 N1 178.0(3) n
N2 N1 C11 O2 -166.7(3) n
C10 N1 C11 O2 -30.0(5) n
N2 N1 C11 N3 12.7(3) n
C10 N1 C11 N3 149.4(3) n
N1 N2 C12 O3 -168.2(3) n
C7 N2 C12 O3 -26.9(5) n
N1 N2 C12 N3 12.2(3) n
C7 N2 C12 N3 153.5(3) n
C11 N3 C12 O3 176.0(3) n
C13 N3 C12 O3 -7.3(5) n
C11 N3 C12 N2 -4.5(4) n
C13 N3 C12 N2 172.3(3) n
