#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2010167.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_2010167
_journal_name_full  'Acta Crystallographica'
_journal_year  1994
_journal_volume  C50
_journal_page_first  1774
_journal_page_last  1777
_publ_section_title
;
The Molecular Structure of Caroxazone, a Reversible Monoamine
Oxidase Inhibitor
;
loop_
_publ_author_name
  'Wouters, Johan'
  'Evrard, Guy'
  'Durant, Francois'
_chemical_name_common  'CAROXAZONE'
_chemical_formula_sum  'C10 H10 N2 O3'
_chemical_formula_weight  206.20
_symmetry_cell_setting  'orthorhombic'
_symmetry_space_group_name_H-M  'P c a 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, z+1/2'
  'x+1/2, -y, z'
  '-x+1/2, y, z+1/2'
_cell_length_a  8.0934(10)
_cell_length_b  19.998(3)
_cell_length_c  11.926(2)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  1930.2(5)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.419
_diffrn_ambient_temperature  293(2)
_refine_ls_R_factor_obs  0.0357
_refine_ls_wR_factor_obs  0.0852
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_occupancy
  O101 .0596(3) .45533(10) .5469(2) .0600(7) Uani 1
  O107 .0030(2) .43034(9) .8109(2) .0502(6) Uani 1
  O115 .0484(2) .34889(9) .50010(17) .0526(6) Uani 1
  N103 .2126(2) .38310(10) .64972(18) .0415(6) Uani 1
  N106 .1785(3) .51049(12) .8679(2) .0516(8) Uani 1
  C102 .1055(3) .39867(13) .5670(2) .0458(8) Uani 1
  C104 .2671(3) .43790(12) .7203(3) .0453(8) Uani 1
  C105 .1362(3) .45942(11) .8049(2) .0379(7) Uani 1
  C108 .2411(4) .31573(12) .6912(2) .0460(8) Uani 1
  C109 .1925(3) .26450(13) .6067(2) .0439(8) Uani 1
  C110 .2406(5) .19787(13) .6161(3) .0591(10) Uani 1
  C111 .1927(5) .15205(16) .5354(4) .0726(13) Uani 1
  C112 .0968(5) .17135(18) .4464(3) .0729(11) Uani 1
  C113 .0503(4) .23774(17) .4342(3) .0593(10) Uani 1
  C114 .0997(3) .28295(14) .5148(2) .0446(8) Uani 1
  O201 .0900(3) .91217(13) .4286(3) .0853(10) Uani 1
  O207 -.0244(2) .93474(9) .7253(2) .0628(7) Uani 1
  O215 .1022(3) .80417(10) .45814(18) .0591(7) Uani 1
  N203 .2082(3) .87741(10) .5906(2) .0500(7) Uani 1
  N206 .1426(3) 1.02019(13) .7729(3) .0629(10) Uani 1
  C202 .1313(4) .86743(14) .4913(3) .0534(9) Uani 1
  C204 .2345(5) .94455(14) .6299(4) .0645(10) Uani 1
  C205 .1060(3) .96569(12) .7162(3) .0493(8) Uani 1
  C208 .2637(5) .82571(14) .6656(3) .0550(9) Uani 1
  C209 .2126(3) .75786(12) .6287(2) .0418(7) Uani 1
  C210 .2424(4) .70097(14) .6921(3) .0556(9) Uani 1
  C211 .1945(4) .63901(16) .6542(3) .0660(11) Uani 1
  C212 .1128(5) .63274(15) .5543(3) .0623(11) Uani 1
  C213 .0804(4) .68783(16) .4904(3) .0540(9) Uani 1
  C214 .1323(3) .74995(13) .5283(2) .0431(7) Uani 1
  H110 .306(4) .1845(15) .675(4) .072 Uiso 1
  H111 .246(5) .1016(16) .539(3) .08 Uiso 1
  H112 .066(5) .1329(17) .395(4) .084 Uiso 1
  H113 -.009(4) .2566(17) .379(4) .076 Uiso 1
  H141 .359(4) .4188(14) .767(3) .059 Uiso 1
  H142 .298(4) .4778(15) .679(3) .059 Uiso 1
  H161 .275(6) .5300(18) .863(4) .081 Uiso 1
  H162 .116(5) .5262(19) .914(4) .081 Uiso 1
  H181 .172(4) .3087(14) .763(3) .054 Uiso 1
  H182 .363(4) .3106(13) .706(3) .054 Uiso 1
  H210 .298(4) .7068(16) .760(3) .067 Uiso 1
  H211 .214(4) .5968(17) .705(4) .08 Uiso 1
  H212 .079(4) .5875(17) .531(3) .07 Uiso 1
  H213 .032(4) .6859(16) .418(3) .067 Uiso 1
  H241 .234(5) .9724(17) .563(4) .075 Uiso 1
  H242 .346(4) .9556(17) .665(4) .075 Uiso 1
  H261 .240(6) 1.0398(17) .765(4) .09 Uiso 1
  H262 .071(5) 1.0367(19) .838(4) .09 Uiso 1
  H281 .230(5) .8357(15) .745(3) .064 Uiso 1
  H282 .392(4) .8269(14) .664(3) .064 Uiso 1
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
  O101 .0647(12) .0509(10) .0643(13) .0057(10) -.0077(11) .0174(10)
  O107 .0402(9) .0512(10) .0592(11) -.0050(7) .0074(9) -.0003(9)
  O115 .0565(10) .0547(10) .0467(10) .0024(9) -.0145(10) .0010(9)
  N103 .0392(11) .0418(9) .0436(11) .0042(8) -.0032(9) -.0003(9)
  N106 .0458(13) .0592(14) .0499(13) -.0017(11) .0048(12) -.0150(12)
  C102 .0402(13) .0521(14) .0452(15) .0012(12) .0016(11) .0062(12)
  C104 .0379(12) .0469(13) .0511(15) .0009(11) .0021(12) -.0033(12)
  C105 .0354(11) .0395(12) .0389(12) .0016(9) -.0006(10) .0055(10)
  C108 .0471(13) .0463(12) .0447(15) .0034(12) -.0113(13) .0051(12)
  C109 .0383(13) .0468(12) .0466(14) -.0023(10) .0030(11) -.0002(11)
  C110 .0602(17) .0452(13) .072(2) .0026(14) -.0014(17) .0003(15)
  C111 .084(2) .0527(16) .081(3) .0039(17) .008(2) -.0094(18)
  C112 .082(2) .0647(19) .072(2) -.0195(18) .016(2) -.0288(19)
  C113 .0562(17) .0740(19) .0478(16) -.0085(15) .0063(15) -.0084(16)
  C114 .0429(13) .0526(13) .0383(13) -.0029(11) .0025(11) -.0004(11)
  O201 .0844(16) .0727(14) .0988(19) .0032(13) -.0140(16) .0395(15)
  O207 .0467(10) .0495(10) .0921(17) -.0031(9) .0102(12) -.0015(11)
  O215 .0718(12) .0597(11) .0457(11) -.0070(11) -.0174(10) .0080(9)
  N203 .0482(13) .0415(10) .0604(15) .0010(9) .0053(12) -.0011(11)
  N206 .0509(14) .0587(15) .079(2) -.0022(12) .0163(14) -.0124(13)
  C202 .0487(15) .0545(16) .0570(17) .0044(12) .0013(13) .0148(14)
  C204 .0622(18) .0454(13) .086(2) -.0091(15) .0244(19) -.0095(16)
  C205 .0434(13) .0369(12) .0676(18) .0038(11) .0077(14) .0029(13)
  C208 .0601(17) .0529(14) .0521(17) .0060(14) -.0172(15) -.0059(13)
  C209 .0382(12) .0479(12) .0392(13) .0054(10) .0015(11) -.0011(11)
  C210 .0530(15) .0595(15) .0544(17) .0121(14) -.0066(15) .0058(14)
  C211 .068(2) .0530(15) .077(2) .0128(14) .0144(18) .0187(17)
  C212 .068(2) .0458(15) .073(2) -.0035(14) .0219(18) -.0048(15)
  C213 .0544(16) .0641(17) .0436(16) -.0105(13) .0072(13) -.0098(14)
  C214 .0463(13) .0475(13) .0354(12) -.0024(11) .0023(11) .0044(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  O101 C102 . . 1.216(3) yes
  O107 C105 . . 1.227(3) yes
  O115 C102 . . 1.357(3) yes
  O115 C114 . . 1.394(3) yes
  N103 C102 . . 1.350(3) yes
  N103 C104 . . 1.451(4) yes
  N103 C108 . . 1.454(3) yes
  N106 C105 . . 1.313(3) yes
  C104 C105 . . 1.525(4) yes
  C108 C109 . . 1.490(4) yes
  C109 C110 . . 1.393(4) yes
  C109 C114 . . 1.379(3) yes
  C110 C111 . . 1.384(5) yes
  C111 C112 . . 1.370(6) yes
  C112 C113 . . 1.388(5) yes
  C113 C114 . . 1.379(4) yes
  O201 C202 . . 1.213(4) yes
  O207 C205 . . 1.228(3) yes
  O215 C202 . . 1.346(4) yes
  O215 C214 . . 1.391(3) yes
  N203 C202 . . 1.353(4) yes
  N203 C204 . . 1.438(4) yes
  N203 C208 . . 1.439(4) yes
  N206 C205 . . 1.316(4) yes
  C204 C205 . . 1.523(5) yes
  C208 C209 . . 1.485(4) yes
  C209 C210 . . 1.387(4) yes
  C209 C214 . . 1.372(3) yes
  C210 C211 . . 1.375(4) yes
  C211 C212 . . 1.368(5) yes
  C212 C213 . . 1.365(5) yes
  C213 C214 . . 1.387(4) yes