data_2202270
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o1187
_journal_page_last  o1188
_publ_section_title
;
1,3,5-Tris(4-fluorobenzenesulfonyl)-1,3,5-triazacyclohexane
;
loop_
_publ_author_name
  'Gilardi, Richard'
  'Evans, Robin N.'
  'Duddu, Raja'
_chemical_formula_moiety  'C21 H18 F3 N3 O6 S3'
_chemical_formula_sum  'C21 H18 F3 N3 O6 S3'
_chemical_formula_iupac  'C21 H18 F3 N3 O6 S3'
_chemical_formula_weight  561.56
_symmetry_cell_setting  Orthorhombic
_symmetry_space_group_name_H-M  'P n m a'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  '-x, y+1/2, -z'
  'x+1/2, -y+1/2, -z+1/2'
  '-x, -y, -z'
  'x-1/2, y, -z-1/2'
  'x, -y-1/2, z'
  '-x-1/2, y-1/2, z-1/2'
_cell_length_a  12.2603(12)
_cell_length_b  16.4739(13)
_cell_length_c  11.6085(6)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  2344.6(3)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.591
_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
  N1 0.76747(19) 0.2500 0.0933(2) 0.0366(6) Uani d S 1 . . N
  S1 0.76894(6) 0.2500 -0.05061(7) 0.0406(2) Uani d S 1 . . S
  O1A 0.72028(13) 0.32531(11) -0.08186(14) 0.0557(5) Uani d . 1 . . O
  C11 0.9057(2) 0.2500 -0.0955(2) 0.0362(7) Uani d S 1 . . C
  C12 0.95990(19) 0.32300(14) -0.10891(19) 0.0439(5) Uani d . 1 . . C
  H12 0.9223 0.3718 -0.1017 0.053 Uiso calc R 1 . . H
  C13 1.0698(2) 0.32304(14) -0.1330(2) 0.0488(6) Uani d . 1 . . C
  H13 1.1076 0.3715 -0.1425 0.059 Uiso calc R 1 . . H
  C14 1.1222(3) 0.2500 -0.1428(3) 0.0473(8) Uani d S 1 . . C
  F1 1.23089(16) 0.2500 -0.1620(2) 0.0717(7) Uani d S 1 . . F
  C2 0.80070(16) 0.32319(13) 0.15346(19) 0.0378(5) Uani d . 1 . . C
  H2A 0.7637 0.3264 0.2272 0.045 Uiso calc R 1 . . H
  H2B 0.7808 0.3706 0.1085 0.045 Uiso calc R 1 . . H
  N3 0.92022(13) 0.32171(10) 0.17156(14) 0.0329(4) Uani d . 1 . . N
  S3 0.97596(4) 0.40764(3) 0.21495(5) 0.03618(17) Uani d . 1 . . S
  O3A 1.09081(11) 0.39392(10) 0.21603(15) 0.0472(4) Uani d . 1 . . O
  O3B 0.92995(14) 0.46931(10) 0.14423(14) 0.0501(4) Uani d . 1 . . O
  C31 0.93145(17) 0.42054(12) 0.35776(19) 0.0356(5) Uani d . 1 . . C
  C32 0.99331(18) 0.38818(14) 0.4467(2) 0.0441(5) Uani d . 1 . . C
  H32 1.0603 0.3640 0.4314 0.053 Uiso calc R 1 . . H
  C33 0.9546(2) 0.39232(15) 0.5577(2) 0.0493(6) Uani d . 1 . . C
  H33 0.9950 0.3715 0.6187 0.059 Uiso calc R 1 . . H
  C34 0.8552(2) 0.42777(15) 0.5763(2) 0.0488(6) Uani d . 1 . . C
  F3 0.81735(14) 0.43195(11) 0.68598(13) 0.0720(5) Uani d . 1 . . F
  C35 0.79260(19) 0.46008(15) 0.4901(2) 0.0492(6) Uani d . 1 . . C
  H35 0.7256 0.4840 0.5063 0.059 Uiso calc R 1 . . H
  C36 0.83109(17) 0.45631(14) 0.3793(2) 0.0427(5) Uani d . 1 . . C
  H36 0.7902 0.4776 0.3189 0.051 Uiso calc R 1 . . H
  C4 0.9539(2) 0.2500 0.2365(3) 0.0337(6) Uani d S 1 . . C
  H4A 1.0324 0.2500 0.2468 0.040 Uiso calc SR 1 . . H
  H4B 0.9198 0.2500 0.3119 0.040 Uiso calc SR 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
  N1 0.0261(12) 0.0472(15) 0.0364(13) 0.000 -0.0024(10) 0.000
  S1 0.0281(4) 0.0561(5) 0.0377(4) 0.000 -0.0042(3) 0.000
  O1A 0.0435(9) 0.0757(12) 0.0480(9) 0.0179(9) -0.0049(8) 0.0107(9)
  C11 0.0321(15) 0.0435(17) 0.0331(15) 0.000 0.0010(12) 0.000
  C12 0.0438(12) 0.0397(12) 0.0482(13) 0.0045(10) 0.0043(10) 0.0040(10)
  C13 0.0478(13) 0.0445(14) 0.0542(14) -0.0103(11) 0.0068(11) 0.0050(11)
  C14 0.0341(16) 0.060(2) 0.0481(19) 0.000 0.0079(14) 0.000
  F1 0.0368(11) 0.0877(17) 0.0905(17) 0.000 0.0144(11) 0.000
  C2 0.0253(10) 0.0466(13) 0.0415(11) 0.0064(9) -0.0025(8) -0.0024(10)
  N3 0.0243(8) 0.0370(10) 0.0374(9) 0.0027(7) -0.0024(7) 0.0001(7)
  S3 0.0290(3) 0.0341(3) 0.0455(3) -0.0004(2) 0.0005(2) 0.0034(2)
  O3A 0.0277(7) 0.0485(9) 0.0655(11) -0.0041(7) 0.0044(7) 0.0019(8)
  O3B 0.0523(10) 0.0409(9) 0.0571(10) 0.0028(8) -0.0008(8) 0.0133(8)
  C31 0.0301(10) 0.0324(11) 0.0444(11) 0.0005(8) -0.0042(9) -0.0041(9)
  C32 0.0343(11) 0.0449(12) 0.0531(14) 0.0053(10) -0.0076(10) -0.0054(11)
  C33 0.0525(14) 0.0514(14) 0.0441(13) 0.0043(12) -0.0125(11) -0.0047(11)
  C34 0.0539(14) 0.0484(13) 0.0441(13) -0.0055(11) 0.0031(11) -0.0142(11)
  F3 0.0812(12) 0.0852(12) 0.0496(9) 0.0033(9) 0.0109(8) -0.0173(8)
  C35 0.0396(12) 0.0487(14) 0.0593(15) 0.0054(11) 0.0035(11) -0.0139(12)
  C36 0.0342(11) 0.0408(12) 0.0531(13) 0.0054(10) -0.0047(10) -0.0054(11)
  C4 0.0287(14) 0.0342(15) 0.0382(15) 0.000 -0.0038(12) 0.000
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
  N1 C2 . 1.452(2) ?
  N1 C2 7_565 1.452(2) ?
  N1 S1 . 1.670(3) ?
  S1 O1A 7_565 1.4237(17) ?
  S1 O1A . 1.4237(17) ?
  S1 C11 . 1.756(3) ?
  C11 C12 . 1.383(3) ?
  C11 C12 7_565 1.383(3) ?
  C12 C13 . 1.376(3) ?
  C12 H12 . 0.9300 ?
  C13 C14 . 1.369(3) ?
  C13 H13 . 0.9300 ?
  C14 F1 . 1.351(4) ?
  C14 C13 7_565 1.369(3) ?
  C2 N3 . 1.481(2) ?
  C2 H2A . 0.9700 ?
  C2 H2B . 0.9700 ?
  N3 C4 . 1.461(2) ?
  N3 S3 . 1.6506(17) ?
  S3 O3B . 1.4228(16) ?
  S3 O3A . 1.4262(15) ?
  S3 C31 . 1.758(2) ?
  C31 C36 . 1.387(3) ?
  C31 C32 . 1.388(3) ?
  C32 C33 . 1.374(3) ?
  C32 H32 . 0.9300 ?
  C33 C34 . 1.368(3) ?
  C33 H33 . 0.9300 ?
  C34 F3 . 1.357(3) ?
  C34 C35 . 1.369(4) ?
  C35 C36 . 1.372(3) ?
  C35 H35 . 0.9300 ?
  C36 H36 . 0.9300 ?
  C4 N3 7_565 1.461(2) ?
  C4 H4A . 0.9700 ?
  C4 H4B . 0.9700 ?