#------------------------------------------------------------------------------
#$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008261.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_2008261
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_journal_page_first  461
_journal_page_last  464
_publ_section_title
;
 4-Ethyl-2,3-dihydro-4H-pyrido[3,2-e]-1,2,4-thiadiazine 1,1-dioxide and
 4-ethyl-2,3-dihydro-4H-pyrido[4,3-e]-1,2,4-thiadiazine 1,1-dioxide
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
loop_
_publ_author_name
  "Dupont, L\'eon"
  'Pirotte, Bernard'
  'Podona, Tchao'
  'Diouf, Ousmane'
  'Delarge, Jacques'
  'De Tullio, Pascal'
_chemical_formula_sum  'C8 H11 N3 O2 S'
_chemical_formula_weight  213.26
_symmetry_cell_setting  monoclinic
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'
_cell_length_a  7.7385(12)
_cell_length_b  12.199(3)
_cell_length_c  20.667(2)
_cell_angle_alpha  90.00
_cell_angle_beta  99.735(18)
_cell_angle_gamma  90.00
_cell_volume  1922.9(6)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.473
_diffrn_ambient_temperature  293(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 0.14942(12) 0.71522(8) -0.00547(4) 0.0581(3) Uani d . 1 . . S
  O1 0.3167(3) 0.7674(2) -0.00217(12) 0.0807(8) Uani d . 1 . . O
  O2 0.1149(3) 0.6189(2) -0.04504(11) 0.0754(8) Uani d . 1 . . O
  N2 0.1228(4) 0.6860(3) 0.06925(12) 0.0603(8) Uani d . 1 . . N
  H2 0.189(5) 0.737(3) 0.0909(17) 0.072 Uiso d . 1 . . H
  C3 -0.0565(5) 0.6706(3) 0.07631(16) 0.0652(10) Uani d . 1 . . C
  H3A -0.0604 0.6448 0.1204 0.078 Uiso calc R 1 . . H
  H3B -0.1076 0.6141 0.0459 0.078 Uiso calc R 1 . . H
  N4 -0.1615(4) 0.7687(3) 0.06442(13) 0.0680(9) Uani d . 1 . . N
  C5 -0.1486(4) 0.8298(3) 0.00950(15) 0.0518(8) Uani d . 1 . . C
  C6 -0.2616(5) 0.9161(3) -0.01229(18) 0.0670(10) Uani d . 1 . . C
  H6 -0.3464 0.9373 0.0121 0.080 Uiso calc R 1 . . H
  C7 -0.2483(5) 0.9700(3) -0.06969(18) 0.0693(10) Uani d . 1 . . C
  H7 -0.3231 1.0282 -0.0837 0.083 Uiso calc R 1 . . H
  C8 -0.1239(5) 0.9377(3) -0.10660(18) 0.0643(9) Uani d . 1 . . C
  H8 -0.1213 0.9719 -0.1466 0.077 Uiso calc R 1 . . H
  N9 -0.0087(4) 0.8598(2) -0.08674(12) 0.0578(7) Uani d . 1 . . N
  C10 -0.0199(4) 0.8099(3) -0.02997(14) 0.0493(8) Uani d . 1 . . C
  C11 -0.2944(5) 0.7877(3) 0.10599(19) 0.0714(10) Uani d . 1 . . C
  H11A -0.3161 0.7198 0.1277 0.086 Uiso calc R 1 . . H
  H11B -0.4032 0.8100 0.0787 0.086 Uiso calc R 1 . . H
  C12 -0.2395(6) 0.8725(4) 0.1558(2) 0.0978(14) Uani d . 1 . . C
  H12A -0.1324 0.8504 0.1832 0.147 Uiso calc R 1 . . H
  H12B -0.3292 0.8821 0.1823 0.147 Uiso calc R 1 . . H
  H12C -0.2212 0.9404 0.1345 0.147 Uiso calc R 1 . . H
  S11 -0.67201(11) 0.75914(7) 0.24412(3) 0.0496(3) Uani d . 1 . . S
  O11 -0.5671(3) 0.6645(2) 0.23990(11) 0.0675(7) Uani d . 1 . . O
  O12 -0.7203(3) 0.8250(2) 0.18624(10) 0.0642(7) Uani d . 1 . . O
  N12 -0.5709(4) 0.8374(2) 0.30215(12) 0.0516(7) Uani d . 1 . . N
  H12 -0.524(4) 0.790(3) 0.3326(16) 0.062 Uiso d . 1 . . H
  C13 -0.6878(4) 0.9157(3) 0.32651(16) 0.0549(8) Uani d . 1 . . C
  H13A -0.6185 0.9671 0.3559 0.066 Uiso calc R 1 . . H
  H13B -0.7512 0.9568 0.2899 0.066 Uiso calc R 1 . . H
  N14 -0.8123(4) 0.8615(2) 0.36103(12) 0.0512(7) Uani d . 1 . . N
  C15 -0.9109(4) 0.7778(2) 0.32944(14) 0.0459(7) Uani d . 1 . . C
  C16 -1.0617(4) 0.7371(3) 0.34983(17) 0.0573(8) Uani d . 1 . . C
  H16 -1.0997 0.7675 0.3862 0.069 Uiso calc R 1 . . H
  C17 -1.1537(5) 0.6531(3) 0.31661(18) 0.0655(10) Uani d . 1 . . C
  H17 -1.2539 0.6261 0.3304 0.079 Uiso calc R 1 . . H
  C18 -1.0969(5) 0.6082(3) 0.26219(18) 0.0681(10) Uani d . 1 . . C
  H18 -1.1625 0.5523 0.2393 0.082 Uiso calc R 1 . . H
  N19 -0.9537(4) 0.6415(2) 0.24177(13) 0.0587(7) Uani d . 1 . . N
  C20 -0.8634(4) 0.7243(3) 0.27453(14) 0.0443(7) Uani d . 1 . . C
  C21 -0.8674(5) 0.9203(3) 0.41556(15) 0.0595(9) Uani d . 1 . . C
  H21A -0.7670 0.9588 0.4397 0.071 Uiso calc R 1 . . H
  H21B -0.9061 0.8675 0.4451 0.071 Uiso calc R 1 . . H
  C22 -1.0126(5) 1.0017(3) 0.39495(19) 0.0775(12) Uani d . 1 . . C
  H22A -0.9749 1.0553 0.3663 0.116 Uiso calc R 1 . . H
  H22B -1.0413 1.0376 0.4331 0.116 Uiso calc R 1 . . H
  H22C -1.1141 0.9642 0.3723 0.116 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 0.0617(5) 0.0701(6) 0.0402(4) 0.0151(4) 0.0019(3) -0.0068(4)
  O1 0.0565(15) 0.119(2) 0.0641(16) 0.0014(15) 0.0043(12) -0.0034(15)
  O2 0.0973(19) 0.0714(17) 0.0542(14) 0.0275(15) 0.0028(13) -0.0221(12)
  N2 0.071(2) 0.067(2) 0.0390(15) 0.0160(16) -0.0004(13) -0.0013(13)
  C3 0.079(3) 0.066(2) 0.0497(19) 0.009(2) 0.0087(18) 0.0101(17)
  N4 0.078(2) 0.081(2) 0.0482(15) 0.0216(17) 0.0203(15) 0.0100(15)
  C5 0.0547(19) 0.0530(19) 0.0462(17) 0.0092(16) 0.0046(14) -0.0043(15)
  C6 0.069(2) 0.068(2) 0.064(2) 0.0163(19) 0.0119(19) -0.0024(19)
  C7 0.078(3) 0.053(2) 0.069(2) 0.0161(19) -0.007(2) 0.0038(19)
  C8 0.078(2) 0.058(2) 0.0542(19) -0.005(2) 0.0014(18) 0.0067(17)
  N9 0.0676(19) 0.0594(19) 0.0442(14) -0.0022(15) 0.0027(13) 0.0028(13)
  C10 0.0572(19) 0.0470(18) 0.0403(16) 0.0037(15) -0.0014(14) -0.0058(14)
  C11 0.070(2) 0.077(3) 0.069(2) -0.004(2) 0.0153(19) 0.001(2)
  C12 0.116(4) 0.081(3) 0.101(3) 0.005(3) 0.029(3) -0.027(3)
  S11 0.0569(5) 0.0547(5) 0.0372(4) 0.0003(4) 0.0078(3) -0.0007(3)
  O11 0.0734(17) 0.0682(16) 0.0631(15) 0.0136(13) 0.0177(13) -0.0092(12)
  O12 0.0789(17) 0.0746(17) 0.0375(11) -0.0097(13) 0.0050(11) 0.0139(11)
  N12 0.0514(16) 0.0610(18) 0.0413(14) -0.0063(13) 0.0041(12) -0.0019(12)
  C13 0.062(2) 0.0471(19) 0.0550(18) -0.0071(16) 0.0097(16) -0.0076(15)
  N14 0.0602(17) 0.0482(15) 0.0473(13) -0.0036(13) 0.0152(12) -0.0087(12)
  C15 0.0534(18) 0.0424(17) 0.0406(15) 0.0048(14) 0.0047(13) 0.0035(13)
  C16 0.059(2) 0.058(2) 0.0578(18) 0.0034(17) 0.0184(16) 0.0040(17)
  C17 0.060(2) 0.062(2) 0.076(2) -0.0095(19) 0.0167(19) 0.010(2)
  C18 0.074(2) 0.064(2) 0.065(2) -0.025(2) 0.0067(19) -0.0043(18)
  N19 0.0708(19) 0.0544(17) 0.0497(15) -0.0128(15) 0.0069(14) -0.0054(13)
  C20 0.0457(16) 0.0480(18) 0.0380(14) -0.0007(14) 0.0038(12) 0.0019(13)
  C21 0.084(2) 0.051(2) 0.0446(17) 0.0044(18) 0.0128(17) -0.0058(15)
  C22 0.102(3) 0.055(2) 0.084(3) 0.020(2) 0.041(2) 0.001(2)
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 O2 . 1.431(2) no
  S1 O1 . 1.433(3) no
  S1 N2 . 1.632(3) yes
  S1 C10 . 1.756(3) no
  N2 C3 . 1.432(5) yes
  N2 H2 . 0.87(3) yes
  C3 N4 . 1.443(4) yes
  C3 H3A . 0.9700 ?
  C3 H3B . 0.9700 ?
  N4 C5 . 1.376(4) yes
  N4 C11 . 1.466(5) yes
  C5 C6 . 1.393(4) no
  C5 C10 . 1.411(4) no
  C6 C7 . 1.375(5) no
  C6 H6 . 0.9300 ?
  C7 C8 . 1.383(5) no
  C7 H7 . 0.9300 ?
  C8 N9 . 1.320(4) no
  C8 H8 . 0.9300 ?
  N9 C10 . 1.338(4) no
  C11 C12 . 1.471(5) no
  C11 H11A . 0.9700 ?
  C11 H11B . 0.9700 ?
  C12 H12A . 0.9600 ?
  C12 H12B . 0.9600 ?
  C12 H12C . 0.9600 ?
  S11 O11 . 1.423(2) no
  S11 O12 . 1.437(2) no
  S11 N12 . 1.627(3) yes
  S11 C20 . 1.756(3) no
  N12 C13 . 1.462(4) yes
  N12 H12 . 0.88(3) yes
  C13 N14 . 1.452(4) yes
  C13 H13A . 0.9700 ?
  C13 H13B . 0.9700 ?
  N14 C15 . 1.372(4) yes
  N14 C21 . 1.459(4) yes
  C15 C16 . 1.397(4) no
  C15 C20 . 1.410(4) no
  C16 C17 . 1.365(5) no
  C16 H16 . 0.9300 ?
  C17 C18 . 1.388(5) no
  C17 H17 . 0.9300 ?
  C18 N19 . 1.315(4) no
  C18 H18 . 0.9300 ?
  N19 C20 . 1.344(4) no
  C21 C22 . 1.506(5) no
  C21 H21A . 0.9700 ?
  C21 H21B . 0.9700 ?
  C22 H22A . 0.9600 ?
  C22 H22B . 0.9600 ?
  C22 H22C . 0.9600 ?
_cod_database_code 2008261