data_2008262
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_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
;
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
_symmetry_space_group_name_H-M  'P 21/n'
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  8.1628(4)
_cell_length_b  11.6259(8)
_cell_length_c  10.2405(11)
_cell_angle_alpha  90.00
_cell_angle_beta  97.841(7)
_cell_angle_gamma  90.00
_cell_volume  962.74(13)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.471
_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 0.10972(7) 0.83708(5) 0.45879(6) 0.0424(2) Uani d . 1 . . S
  O1 -0.0357(2) 0.82737(19) 0.36454(19) 0.0612(6) Uani d . 1 . . O
  O2 0.0975(2) 0.88891(16) 0.58352(17) 0.0549(5) Uani d . 1 . . O
  N2 0.1875(3) 0.70919(19) 0.4866(2) 0.0482(5) Uani d . 1 . . N
  H2 0.182(4) 0.676(3) 0.423(3) 0.058 Uiso d . 1 . . H
  C3 0.3488(3) 0.7137(2) 0.5623(3) 0.0507(6) Uani d . 1 . . C
  H3A 0.3862 0.6358 0.5831 0.061 Uiso calc R 1 . . H
  H3B 0.3410 0.7529 0.6448 0.061 Uiso calc R 1 . . H
  N4 0.4720(2) 0.77219(18) 0.4949(2) 0.0464(5) Uani d . 1 . . N
  C5 0.4299(3) 0.86057(19) 0.4111(2) 0.0388(5) Uani d . 1 . . C
  C6 0.5442(3) 0.9170(2) 0.3419(3) 0.0500(6) Uani d . 1 . . C
  H6 0.6542 0.8935 0.3520 0.060 Uiso calc R 1 . . H
  C7 0.4927(4) 1.0066(2) 0.2597(3) 0.0551(7) Uani d . 1 . . C
  H7 0.5722 1.0419 0.2165 0.066 Uiso calc R 1 . . H
  N8 0.3390(3) 1.04780(19) 0.2359(2) 0.0534(6) Uani d . 1 . . N
  C9 0.2288(3) 0.9947(2) 0.2995(2) 0.0453(6) Uani d . 1 . . C
  H9 0.1199 1.0203 0.2850 0.054 Uiso calc R 1 . . H
  C10 0.2661(3) 0.90383(19) 0.3859(2) 0.0367(5) Uani d . 1 . . C
  C11 0.6431(3) 0.7332(2) 0.5300(3) 0.0531(7) Uani d . 1 . . C
  H11A 0.6599 0.7098 0.6218 0.064 Uiso calc R 1 . . H
  H11B 0.7176 0.7966 0.5200 0.064 Uiso calc R 1 . . H
  C12 0.6839(4) 0.6343(3) 0.4458(3) 0.0704(9) Uani d . 1 . . C
  H12A 0.7949 0.6090 0.4745 0.106 Uiso calc R 1 . . H
  H12B 0.6745 0.6586 0.3555 0.106 Uiso calc R 1 . . H
  H12C 0.6084 0.5722 0.4536 0.106 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 0.0394(3) 0.0486(4) 0.0405(4) -0.0022(3) 0.0099(2) -0.0049(3)
  O1 0.0395(9) 0.0807(14) 0.0612(12) -0.0095(9) -0.0009(8) -0.0048(10)
  O2 0.0655(12) 0.0594(11) 0.0430(10) 0.0065(9) 0.0192(9) -0.0082(8)
  N2 0.0553(13) 0.0434(12) 0.0478(12) -0.0071(10) 0.0138(10) -0.0052(9)
  C3 0.0615(16) 0.0452(14) 0.0472(14) 0.0065(12) 0.0144(12) 0.0085(11)
  N4 0.0436(12) 0.0465(12) 0.0493(11) 0.0037(9) 0.0075(9) 0.0096(9)
  C5 0.0419(12) 0.0368(12) 0.0375(12) -0.0002(9) 0.0048(9) -0.0023(9)
  C6 0.0422(13) 0.0514(15) 0.0579(16) -0.0013(11) 0.0121(11) 0.0049(12)
  C7 0.0596(17) 0.0523(16) 0.0565(16) -0.0057(13) 0.0189(13) 0.0078(13)
  N8 0.0657(15) 0.0460(13) 0.0497(12) 0.0012(10) 0.0125(11) 0.0088(10)
  C9 0.0502(14) 0.0427(13) 0.0425(12) 0.0064(11) 0.0050(10) -0.0007(10)
  C10 0.0388(12) 0.0375(12) 0.0341(11) -0.0015(9) 0.0060(9) -0.0038(9)
  C11 0.0503(15) 0.0568(16) 0.0510(15) 0.0108(12) 0.0030(12) 0.0048(12)
  C12 0.072(2) 0.0631(19) 0.079(2) 0.0133(16) 0.0224(17) -0.0007(16)
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 . 1.4280(18) no
  S1 O1 . 1.4283(19) no
  S1 N2 . 1.627(2) yes
  S1 C10 . 1.746(2) no
  N2 C3 . 1.435(3) yes
  N2 H2 . 0.75(3) yes
  C3 N4 . 1.463(3) yes
  C3 H3A . 0.9700 ?
  C3 H3B . 0.9700 ?
  N4 C5 . 1.353(3) yes
  N4 C11 . 1.465(3) yes
  C5 C6 . 1.409(3) no
  C5 C10 . 1.418(3) no
  C6 C7 . 1.369(4) no
  C6 H6 . 0.9300 ?
  C7 N8 . 1.334(4) no
  C7 H7 . 0.9300 ?
  N8 C9 . 1.333(3) no
  C9 C10 . 1.385(3) no
  C9 H9 . 0.9300 ?
  C11 C12 . 1.502(4) no
  C11 H11A . 0.9700 ?
  C11 H11B . 0.9700 ?
  C12 H12A . 0.9600 ?
  C12 H12B . 0.9600 ?
  C12 H12C . 0.9600 ?