#------------------------------------------------------------------------------
#$Date: 2011-09-28 17:24:46 +0300 (Wed, 28 Sep 2011) $
#$Revision: 26848 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/06/2200681.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_2200681
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2001
_journal_volume  57
_journal_page_first  o1126
_journal_page_last  o1127
_publ_section_title
;
3-M\'ethyl-1-(pyridin-2-yl)-4-(1-pyridin-2-yl-3-m\'ethyl-1H-pyrazol-5-yl)
-2H-3-pyrazolin-5(1H)-one
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
loop_
_publ_author_name
  ' Djerrari, B.'
  'Essassi, E. M.'
  ' Fifani, J.'
  'Pierrot, M.'
_chemical_formula_moiety  'C18 H16 N6 O'
_chemical_formula_sum  'C18 H16 N6 O'
_chemical_formula_iupac  'C18 H16 N6 O'
_chemical_formula_weight  332.37
_symmetry_cell_setting  monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  '+X,+Y,+Z'
  '-X,-Y,-Z'
  '-X,+Y+ 1/2,-Z+ 1/2'
  '+X,-Y+ 1/2,+Z+ 1/2'
_cell_length_a  18.297(2)
_cell_length_b  7.7645(9)
_cell_length_c  11.9280(8)
_cell_angle_alpha  90.00
_cell_angle_beta  102.681(7)
_cell_angle_gamma  90.00
_cell_volume  1653.2(3)
_cell_formula_units_Z  4
_cell_measurement_temperature  298
_exptl_crystal_density_diffrn  1.335
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
  O6  .21581(8)  .7957(2)  .15539(12)  .0662(5) Uani d . 1 . . O
  N1  .19078(8)  .7370(2)  .33412(12)  .0423(4) Uani d . 1 . . N
  N2  .22963(9)  .6618(2)  .43448(13)  .0443(4) Uani d . 1 . . N
  H2  .2131  .6476  .4960  .053 Uiso calc R 1 . . H
  N7  .09083(9)  .7782(2)  .41894(14)  .0513(4) Uani d . 1 . . N
  N8  .25259(9)  .3708(2)  .13833(15)  .0555(5) Uani d . 1 . . N
  N11  .36059(8)  .5378(2)  .15296(13)  .0414(4) Uani d . 1 . . N
  N12  .42648(9)  .5433(2)  .11567(15)  .0477(4) Uani d . 1 . . N
  C3  .29760(10)  .6145(2)  .42001(16)  .0393(4) Uani d . 1 . . C
  C4  .30302(10)  .6503(2)  .30970(15)  .0398(4) Uani d . 1 . . C
  C5  .23555(10)  .7331(3)  .25319(15)  .0440(5) Uani d . 1 . . C
  C9  .35265(12)  .5354(3)  .51676(17)  .0527(5) Uani d . 1 . . C
  H9A  .3277  .5029  .5765  .079 Uiso calc PR  .60 . . H
  H9B  .3915  .6172  .5464  .079 Uiso calc PR  .60 . . H
  H9C  .3743  .4352  .4898  .079 Uiso calc PR  .60 . . H
  H9D  .4047  .5304  .5023  .079 Uiso d PR  .40 A 2 H
  H9E  .3565  .6088  .5864  .079 Uiso d PR  .40 A 2 H
  H9F  .3307  .4246  .5360  .079 Uiso d PR  .40 A 2 H
  C10  .55199(12)  .6615(3)  .1839(2)  .0705(7) Uani d . 1 . . C
  H10A  .5588  .6101  .1138  .106 Uiso calc R 1 . . H
  H10B  .5871  .6127  .2477  .106 Uiso calc R 1 . . H
  H10C  .5601  .7835  .1815  .106 Uiso calc R 1 . . H
  C13  .47371(11)  .6276(3)  .19777(19)  .0486(5) Uani d . 1 . . C
  C14  .43901(11)  .6780(3)  .28619(18)  .0489(5) Uani d . 1 . . C
  H14  .4609  .7384  .3524  .059 Uiso calc R 1 . . H
  C15  .36651(10)  .6208(2)  .25591(16)  .0404(4) Uani d . 1 . . C
  C16  .11759(10)  .7980(2)  .32488(16)  .0411(4) Uani d . 1 . . C
  C17  .07751(11)  .8710(3)  .22330(19)  .0528(5) Uani d . 1 . . C
  H17  .0981  .8814  .1590  .063 Uiso calc R 1 . . H
  C18  .00598(12)  .9270(3)  .2223(2)  .0633(6) Uani d . 1 . . C
  H18  -.0230  .9761  .1561  .076 Uiso calc R 1 . . H
  C19  -.02265(13)  .9105(3)  .3191(2)  .0676(7) Uani d . 1 . . C
  H19  -.0706  .9493  .3200  .081 Uiso calc R 1 . . H
  C20  .02120(13)  .8357(3)  .4140(2)  .0626(6) Uani d . 1 . . C
  H20  .0015  .8239  .4792  .075 Uiso calc R 1 . . H
  C21  .29970(10)  .4469(2)  .08349(16)  .0404(4) Uani d . 1 . . C
  C22  .29414(12)  .4379(3)  -.03348(17)  .0528(5) Uani d . 1 . . C
  H22  .3287  .4933  -.0677  .063 Uiso calc R 1 . . H
  C23  .23590(14)  .3445(3)  -.0983(2)  .0693(7) Uani d . 1 . . C
  H23  .2306  .3345  -.1774  .083 Uiso calc R 1 . . H
  C24  .18584(14)  .2664(3)  -.0441(2)  .0736(7) Uani d . 1 . . C
  H24  .1458  .2033  -.0859  .088 Uiso calc R 1 . . H
  C25  .19600(13)  .2829(3)  .0720(2)  .0683(7) Uani d . 1 . . C
  H25  .1615  .2300  .1076  .082 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
  O6  .0659(10)  .1047(13)  .0312(9)  .0195(9)  .0174(6)  .0154(8)
  N1  .0445(9)  .0556(10)  .0283(9)  .0032(7)  .0111(6)  .0006(7)
  N2  .0531(9)  .0532(10)  .0297(9)  .0042(8)  .0159(7)  .0043(7)
  N7  .0522(10)  .0592(11)  .0477(11)  -.0001(8)  .0219(7)  -.0085(8)
  N8  .0522(10)  .0676(12)  .0494(11)  -.0110(9)  .0168(8)  -.0090(8)
  N11  .0414(8)  .0488(10)  .0380(9)  -.0003(7)  .0171(6)  -.0058(7)
  N12  .0441(9)  .0542(10)  .0506(11)  .0006(8)  .0227(7)  -.0039(8)
  C3  .0483(10)  .0368(10)  .0335(11)  -.0010(8)  .0107(7)  -.0039(7)
  C4  .0455(10)  .0452(11)  .0304(11)  .0000(8)  .0120(7)  -.0058(8)
  C5  .0498(11)  .0561(13)  .0284(11)  .0007(9)  .0137(8)  -.0032(8)
  C9  .0620(12)  .0557(13)  .0392(12)  .0050(10)  .0086(9)  .0029(9)
  C10  .0488(12)  .0744(17)  .094(2)  -.0067(11)  .0284(12)  -.0024(14)
  C13  .0442(10)  .0484(12)  .0565(13)  .0007(9)  .0180(9)  .0032(9)
  C14  .0491(11)  .0500(12)  .0472(12)  -.0039(9)  .0101(8)  -.0047(9)
  C15  .0470(10)  .0424(11)  .0336(11)  .0011(8)  .0126(7)  -.0026(8)
  C16  .0448(10)  .0403(11)  .0402(11)  -.0027(8)  .0133(8)  -.0068(8)
  C17  .0537(12)  .0532(13)  .0515(14)  .0021(10)  .0118(9)  .0046(9)
  C18  .0544(13)  .0545(14)  .0783(18)  .0070(10)  .0084(11)  .0098(12)
  C19  .0536(13)  .0590(15)  .095(2)  .0107(11)  .0272(13)  -.0004(13)
  C20  .0601(13)  .0653(15)  .0711(17)  .0049(11)  .0334(12)  -.0075(12)
  C21  .0432(10)  .0405(11)  .0384(11)  .0061(8)  .0108(7)  -.0060(8)
  C22  .0643(13)  .0539(13)  .0412(13)  .0097(10)  .0136(9)  -.0023(9)
  C23  .0807(17)  .0780(17)  .0419(14)  .0117(14)  -.0026(11)  -.0171(11)
  C24  .0607(15)  .0752(18)  .0757(19)  -.0012(13)  -.0049(12)  -.0246(14)
  C25  .0538(13)  .0764(17)  .0745(18)  -.0162(12)  .0138(11)  -.0165(13)
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
  O6 C5 . 1.242(2) ?
  N1 N2 . 1.380(2) ?
  N1 C5 . 1.397(2) ?
  N1 C16 . 1.402(2) ?
  N2 C3 . 1.344(2) ?
  N2 H2 .  .8600 ?
  N7 C16 . 1.328(2) ?
  N7 C20 . 1.339(3) ?
  N8 C21 . 1.330(2) ?
  N8 C25 . 1.343(3) ?
  N11 C15 . 1.370(2) ?
  N11 N12 . 1.374(2) ?
  N11 C21 . 1.421(2) ?
  N12 C13 . 1.328(3) ?
  C3 C4 . 1.370(3) ?
  C3 C9 . 1.488(3) ?
  C4 C5 . 1.423(3) ?
  C4 C15 . 1.463(2) ?
  C9 H9A .  .9600 ?
  C9 H9B .  .9600 ?
  C9 H9C .  .9600 ?
  C9 H9D . 1.0052 ?
  C9 H9E .  .9971 ?
  C9 H9F .  .9970 ?
  C10 C13 . 1.501(3) ?
  C10 H10A .  .9600 ?
  C10 H10B .  .9600 ?
  C10 H10C .  .9600 ?
  C13 C14 . 1.401(3) ?
  C14 C15 . 1.370(3) ?
  C14 H14 .  .9300 ?
  C16 C17 . 1.392(3) ?
  C17 C18 . 1.377(3) ?
  C17 H17 .  .9300 ?
  C18 C19 . 1.375(3) ?
  C18 H18 .  .9300 ?
  C19 C20 . 1.365(3) ?
  C19 H19 .  .9300 ?
  C20 H20 .  .9300 ?
  C21 C22 . 1.378(3) ?
  C22 C23 . 1.378(3) ?
  C22 H22 .  .9300 ?
  C23 C24 . 1.373(4) ?
  C23 H23 .  .9300 ?
  C24 C25 . 1.363(4) ?
  C24 H24 .  .9300 ?
  C25 H25 .  .9300 ?
_cod_database_code 2200681