#------------------------------------------------------------------------------
#$Date: 2009-11-18 14:56:34 +0000 (Wed, 18 Nov 2009) $
#$Revision: 858 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008809.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_2008809
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_journal_page_first  1322
_journal_page_last  1325
_publ_section_title
;
(S)-8-Chloro-5-methyl-6-(3-methylbut-2-enyl)-2-thioxo-1H-4,5,6,7-tetrahydro-
imidazo[4,5,1-jk][1,4]benzodiazepinium bromide methanol solvate
;
loop_
_publ_author_name
  'Peeters, Oswald M.'
  'Blaton, Norbert M.'
  'De Ranter, Camiel J.'
_chemical_formula_moiety  'C16 H21 Cl1 N3 S1 1+, Br1 1-, C1 H4 O1'
_chemical_formula_sum            'C17 H25 Br Cl N3 O S'
_[local]_cod_chemical_formula_sum_orig 'C17 H25 Br1 Cl1 N3 O1 S1'
_chemical_formula_weight  434.82
_symmetry_cell_setting  'Orthorhombic'
_symmetry_space_group_name_H-M  'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
  'X,Y,Z'
  '1/2-X,-Y,1/2+Z'
  '1/2+X,1/2-Y,-Z'
  '-X,1/2+Y,1/2-Z'
_cell_length_a  7.498(4)
_cell_length_b  9.666(5)
_cell_length_c  28.04(2)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  2032.(2)
_cell_formula_units_Z  4
_cell_measurement_temperature  293
_exptl_crystal_density_diffrn  1.421
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_calc_attached_atom
_atom_site_refinement_flags
_atom_site_type_symbol
  Br1 .21935(8) .12722(7) .34131(2) .0602(2) aniso . . . Br
  N1 .2812(6) .1341(4) .45800(10)
  .0490(10)
  aniso . . . N
  C2 .2980(8) .2481(5) .4848(2) .045(2) aniso . . . C
  S2 .2975(2) .41220(10)
  .46544(5) .0575(5) aniso . . . S
  N3 .3212(6) .2053(4) .53100(10)
  .0370(10)
  aniso . . . N
  C4 .3429(7) .2941(5) .5722(2) .042(2) aniso . . . C
  C5 .2075(7) .2644(4) .6107(2) .0400(10)
  aniso . . . C
  C51 .1981(8) .3828(5) .6459(2) .054(2) aniso . . . C
  N6 .2445(5) .1305(4) .63980(10)
  .0390(10)
  aniso . . . N
  C61 .0657(7) .0638(5) .6509(2) .044(2) aniso . . . C
  C62 .0787(7) -.0506(5) .6865(2) .044(2) aniso . . . C
  C63 -.0062(8) -.1670(5) .6841(2) .051(2) aniso . . . C
  C64 -.1190(10)
  -.2101(7) .6422(2) .090(3) aniso . . . C
  C65 .0060(10)
  -.2718(6) .7232(2) .071(2) aniso . . . C
  C7 .3784(7) .0309(5) .6198(2) .044(2) aniso . . . C
  C7a .3338(7) -.0248(5) .5712(2) .042(2) aniso . . . C
  C8 .3261(9) -.1664(5) .5604(2) .056(2) aniso . . . C
  Cl8 .3637(3) -.2887(2) .60465(6) .0834(7) aniso . . . Cl
  C9 .2931(9) -.2141(6) .5142(2) .067(2) aniso . . . C
  C10 .2745(9) -.1240(6) .4765(2) .065(2) aniso . . . C
  C10a .2885(8) .0157(5) .4859(2) .048(2) aniso . . . C
  C10b .3142(7) .0619(5) .5326(2) .040(2) aniso . . . C
  O71 .4487(7) .1870(6) .7194(2) .090(2) aniso . . . O
  C71 .525(2) .1000(10)
  .7518(4) .170(6) aniso . . . C
  H1 .2676 .1342 .4276 .061 iso calc N1 R H
  H4A .3317 .3899 .5623 .052 iso calc C4 R H
  H4B .4618 .2815 .5852 .052 iso calc C4 R H
  H5 .0903 .2551 .5955 .050 iso calc C5 R H
  H51A .3167 .4098 .6548 .067 iso calc C51 R H
  H51B .1336 .3539 .6737 .067 iso calc C51 R H
  H51C .1381 .4599 .6314 .067 iso calc C51 R H
  H6 .2893 .1590 .6683 .048 iso calc N6 R H
  H61A -.0149 .1339 .6630 .055 iso calc C61 R H
  H61B .0150 .0275 .6216 .055 iso calc C61 R H
  H62 .1538 -.0372 .7125 .056 iso calc C62 R H
  H64A -.0897 -.1541 .6150 .112 iso calc C64 R H
  H64B -.2430 -.1979 .6499 .112 iso calc C64 R H
  H64C -.0970 -.3056 .6349 .112 iso calc C64 R H
  H65A .0919 -.2420 .7463 .089 iso calc C65 R H
  H65B .0416 -.3592 .7101 .089 iso calc C65 R H
  H65C -.1086 -.2813 .7382 .089 iso calc C65 R H
  H7A .3902 -.0462 .6417 .055 iso calc C7 R H
  H7B .4933 .0769 .6182 .055 iso calc C7 R H
  H9 .2834 -.3088 .5089 .084 iso calc C9 R H
  H10 .2533 -.1563 .4458 .081 iso calc C10 R H
  H71 .5237 .2415 .7095 .113 iso calc O71 R H
  H71A .5681 .1532 .7785 .213 iso calc C71 R H
  H71B .6232 .0526 .7371 .213 iso calc C71 R H
  H71C .4386 .0345 .7626 .213 iso calc C71 R 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
  Br1 .0551(3) .0813(4) .0443(3) .0025(3) -.0007(3) -.0001(3)
  N1 .054(2) .055(2) .037(2) .000(3) -.002(2) -.007(2)
  C2 .044(3) .045(3) .045(3) .002(3) .001(3) .001(2)
  S2 .0750(10)
  .0490(7) .0489(7) .0049(8) .0025(8) .0126(6)
  N3 .044(3) .034(2) .034(2) -.001(2) -.003(2) .000(2)
  C4 .049(3) .035(2) .041(3) -.002(2) -.004(2) -.001(2)
  C5 .042(3) .035(2) .044(2) -.003(3) -.004(3) .007(2)
  C51 .063(3) .039(3) .059(3) -.004(3) .014(3) .002(3)
  N6 .042(3) .037(2) .038(2) -.006(2) .000(2) .002(2)
  C61 .043(3) .043(3) .045(3) -.006(2) .004(2) .002(2)
  C62 .052(4) .046(3) .035(3) -.010(3) .002(2) .003(2)
  C63 .060(4) .049(3) .044(3) -.009(3) -.003(3) .004(2)
  C64 .113(6) .070(4) .086(5) -.038(5) -.034(4) .015(4)
  C65 .090(5) .059(4) .065(4) -.015(4) .003(4) .014(3)
  C7 .047(3) .039(3) .046(3) .003(3) -.001(3) .009(2)
  C7a .040(3) .039(3) .046(3) .004(2) .009(2) -.004(2)
  C8 .070(4) .036(3) .061(3) .004(3) .014(3) -.002(2)
  Cl8 .126(2) .0390(7) .0860(10)
  .0108(9) .0220(10)
  .0135(8)
  C9 .086(4) .037(3) .078(4) .000(3) .009(4) -.013(3)
  C10 .075(4) .058(3) .062(3) .009(4) -.002(3) -.035(3)
  C10a .054(3) .046(3) .045(3) .000(3) -.001(3) -.004(2)
  C10b .033(3) .040(3) .047(3) -.001(2) .005(2) -.005(2)
  O71 .092(4) .111(4) .068(3) -.039(3) -.027(3) .025(3)
  C71 .123(8) .230(10)
  .157(8) -.053(9) -.036(7) .120(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
  N1 C2 1.339(6) no
  N1 C10a 1.387(6) no
  N1 H1 .860 no
  C2 S2 1.676(5) no
  C2 N3 1.371(6) no
  N3 C4 1.450(6) no
  N3 C10b 1.389(6) no
  C4 C5 1.509(7) no
  C4 H4A .970 no
  C4 H4B .970 no
  C5 C51 1.513(6) no
  C5 N6 1.555(6) no
  C5 H5 .980 no
  C51 H51A .960 no
  C51 H51B .960 no
  C51 H51C .960 no
  N6 C61 1.520(6) no
  N6 C7 1.499(6) no
  N6 H6 .910 no
  C61 C62 1.493(7) no
  C61 H61A .970 no
  C61 H61B .970 no
  C62 C63 1.295(7) no
  C62 H62 .930 no
  C63 C64 1.507(9) no
  C63 C65 1.494(8) no
  C64 H64A .960 no
  C64 H64B .960 no
  C64 H64C .960 no
  C65 H65A .960 no
  C65 H65B .960 no
  C65 H65C .960 no
  C7 C7a 1.504(7) no
  C7 H7A .970 no
  C7 H7B .970 no
  C7a C8 1.403(7) no
  C7a C10b 1.376(7) no
  C8 Cl8 1.736(5) no
  C8 C9 1.396(8) no
  C9 C10 1.377(8) no
  C9 H9 .930 no
  C10 C10a 1.380(8) no
  C10 H10 .930 no
  C10a C10b 1.397(7) no
  O71 C71 1.360(10)
  no
  O71 H71 .820 no
  C71 H71A .960 no
  C71 H71B .960 no
  C71 H71C .960 no