#------------------------------------------------------------------------------
#$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012810.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_2012810
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o423
_journal_page_last  o424
_publ_section_title
;
4,5-Dihydro-3-methyl-5-(4-methylphenyl)-1H-pyrazole-1-carboxamidinium
acetate acetone hemisolvate
;
_space_group_IT_number           15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_[local]_cod_cif_authors_sg_H-M  'C 2/c'
loop_
_publ_author_name
  'Kettmann, Viktor'
  'Sv\<etl\'ik, Jan'
_chemical_formula_moiety  'C12 H17 N4 1+, C2 H3 O2 1-, 0.5C3 H6 O'
_chemical_formula_sum  'C15.5 H23 N4 O2.5'
_chemical_formula_iupac  'C12 H17 N4 1+, C2 H3 O2 1-, 0.5C3 H6 O'
_chemical_formula_weight  305.38
_chemical_melting_point  494
_symmetry_cell_setting  monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y, -z+1/2'
  'x+1/2, y+1/2, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y, z-1/2'
  '-x+1/2, -y+1/2, -z'
  'x+1/2, -y+1/2, z-1/2'
_cell_length_a  27.679(11)
_cell_length_b  8.126(4)
_cell_length_c  18.776(9)
_cell_angle_alpha  90.00
_cell_angle_beta  129.15(6)
_cell_angle_gamma  90.00
_cell_volume  3275(3)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.239
_exptl_crystal_density_meas  1.240(10)
_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 0.17743(14) 0.2915(3) 0.50412(19) 0.0454(7) Uani d . 1 . . N
  N2 0.16536(13) 0.2725(3) 0.42057(19) 0.0461(7) Uani d . 1 . . N
  C3 0.14613(16) 0.1257(4) 0.3935(2) 0.0479(9) Uani d . 1 . . C
  C4 0.14301(18) 0.0254(5) 0.4563(3) 0.0573(10) Uani d . 1 . . C
  H4A 0.1743 -0.0608 0.4850 0.069 Uiso calc R 1 . . H
  H4B 0.1022 -0.0243 0.4239 0.069 Uiso calc R 1 . . H
  C5 0.15579(17) 0.1497(4) 0.5273(3) 0.0492(9) Uani d . 1 . . C
  H5 0.1895 0.1104 0.5895 0.059 Uiso calc R 1 . . H
  C6 0.09914(15) 0.1907(4) 0.5182(2) 0.0425(8) Uani d . 1 . . C
  C7 0.0477(2) 0.2658(5) 0.4397(3) 0.0692(12) Uani d . 1 . . C
  H7 0.0490 0.2960 0.3932 0.083 Uiso calc R 1 . . H
  C8 -0.0058(2) 0.2968(5) 0.4292(3) 0.0696(12) Uani d . 1 . . C
  H8 -0.0396 0.3468 0.3756 0.083 Uiso calc R 1 . . H
  C9 -0.01002(18) 0.2559(4) 0.4956(3) 0.0549(10) Uani d . 1 . . C
  C10 0.0416(2) 0.1807(5) 0.5734(3) 0.0635(11) Uani d . 1 . . C
  H10 0.0403 0.1508 0.6200 0.076 Uiso calc R 1 . . H
  C11 0.09462(18) 0.1488(5) 0.5842(2) 0.0552(10) Uani d . 1 . . C
  H11 0.1281 0.0975 0.6376 0.066 Uiso calc R 1 . . H
  C12 0.1278(2) 0.0647(5) 0.3048(3) 0.0699(12) Uani d . 1 . . C
  H12A 0.0835 0.0491 0.2621 0.105 Uiso calc R 1 . . H
  H12B 0.1483 -0.0381 0.3146 0.105 Uiso calc R 1 . . H
  H12C 0.1398 0.1437 0.2805 0.105 Uiso calc R 1 . . H
  C13 -0.0670(2) 0.2871(6) 0.4847(4) 0.0774(13) Uani d . 1 . . C
  H13A -0.0792 0.4001 0.4680 0.116 Uiso calc R 1 . . H
  H13B -0.0589 0.2645 0.5415 0.116 Uiso calc R 1 . . H
  H13C -0.1000 0.2170 0.4374 0.116 Uiso calc R 1 . . H
  C14 0.20306(15) 0.4303(4) 0.5505(2) 0.0403(8) Uani d . 1 . . C
  N3 0.21865(13) 0.4504(4) 0.63275(19) 0.0498(8) Uani d . 1 . . N
  H3A 0.2348 0.5417 0.6617 0.060 Uiso calc R 1 . . H
  H3B 0.2126 0.3720 0.6571 0.060 Uiso calc R 1 . . H
  N4 0.21280(13) 0.5522(3) 0.51449(18) 0.0496(8) Uani d . 1 . . N
  H4C 0.2025 0.5415 0.4609 0.059 Uiso calc R 1 . . H
  H4D 0.2295 0.6423 0.5446 0.059 Uiso calc R 1 . . H
  C15 0.21155(16) 0.3530(4) 0.8083(2) 0.0449(9) Uani d . 1 . . C
  O1 0.23153(12) 0.2668(3) 0.77709(17) 0.0539(7) Uani d . 1 . . O
  O2 0.21850(15) 0.3199(3) 0.87874(18) 0.0716(9) Uani d . 1 . . O
  C16 0.1751(2) 0.5045(5) 0.7577(3) 0.0626(11) Uani d . 1 . . C
  H16A 0.1391 0.4756 0.6965 0.094 Uiso calc R 1 . . H
  H16B 0.2006 0.5796 0.7550 0.094 Uiso calc R 1 . . H
  H16C 0.1620 0.5557 0.7891 0.094 Uiso calc R 1 . . H
  C17 0.0000 0.6922(10) 0.2500 0.085(2) Uani d S 1 . . C
  O3 0.0000 0.8463(8) 0.2500 0.161(3) Uani d S 1 . . O
  C18 0.0542(3) 0.6072(8) 0.2821(5) 0.116(2) Uani d . 1 . . C
  H18A 0.0876 0.6841 0.3064 0.174 Uiso calc R 1 . . H
  H18B 0.0473 0.5469 0.2325 0.174 Uiso calc R 1 . . H
  H18C 0.0649 0.5321 0.3296 0.174 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
  N1 0.0565(18) 0.0421(16) 0.0458(16) -0.0134(14) 0.0362(15) -0.0071(13)
  N2 0.0495(17) 0.0458(18) 0.0436(16) -0.0062(14) 0.0297(15) -0.0072(13)
  C3 0.049(2) 0.044(2) 0.051(2) -0.0058(17) 0.0311(18) -0.0075(17)
  C4 0.060(2) 0.045(2) 0.068(3) -0.0066(18) 0.041(2) -0.0076(18)
  C5 0.050(2) 0.042(2) 0.053(2) -0.0043(16) 0.0320(18) 0.0030(16)
  C6 0.047(2) 0.0366(18) 0.0429(19) -0.0055(15) 0.0277(17) 0.0000(15)
  C7 0.074(3) 0.083(3) 0.069(3) 0.019(2) 0.054(2) 0.031(2)
  C8 0.065(3) 0.082(3) 0.068(3) 0.020(2) 0.045(2) 0.030(2)
  C9 0.054(2) 0.047(2) 0.069(3) -0.0031(18) 0.042(2) -0.0012(19)
  C10 0.070(3) 0.080(3) 0.058(2) 0.003(2) 0.049(2) 0.008(2)
  C11 0.055(2) 0.063(3) 0.0399(19) -0.0011(19) 0.0267(18) 0.0051(18)
  C12 0.083(3) 0.058(3) 0.065(3) -0.012(2) 0.045(2) -0.020(2)
  C13 0.073(3) 0.077(3) 0.103(4) -0.001(2) 0.065(3) 0.004(3)
  C14 0.0409(18) 0.045(2) 0.0382(18) -0.0037(15) 0.0263(15) 0.0013(15)
  N3 0.0664(19) 0.0478(18) 0.0451(16) -0.0100(15) 0.0400(15) -0.0037(14)
  N4 0.068(2) 0.0448(17) 0.0385(15) -0.0167(15) 0.0348(15) -0.0087(13)
  C15 0.053(2) 0.047(2) 0.0383(19) -0.0004(17) 0.0306(17) -0.0006(15)
  O1 0.0665(16) 0.0561(16) 0.0494(14) 0.0191(13) 0.0415(14) 0.0113(12)
  O2 0.120(3) 0.0592(17) 0.0576(17) 0.0308(16) 0.0662(18) 0.0195(14)
  C16 0.084(3) 0.058(2) 0.064(2) 0.021(2) 0.055(2) 0.017(2)
  C17 0.095(6) 0.079(5) 0.076(5) 0.000 0.052(4) 0.000
  O3 0.097(4) 0.104(5) 0.238(9) 0.000 0.085(5) 0.000
  C18 0.103(4) 0.126(5) 0.140(5) 0.045(4) 0.087(4) 0.033(4)
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 C14 . 1.324(4) yes
  N1 N2 . 1.391(4) yes
  N1 C5 . 1.485(4) yes
  N2 C3 . 1.274(4) yes
  C3 C4 . 1.481(5) yes
  C3 C12 . 1.486(5) ?
  C4 C5 . 1.526(5) yes
  C4 H4A . 0.9700 ?
  C4 H4B . 0.9700 ?
  C5 C6 . 1.503(5) yes
  C5 H5 . 0.9800 ?
  C6 C11 . 1.365(5) ?
  C6 C7 . 1.387(5) ?
  C7 C8 . 1.386(6) ?
  C7 H7 . 0.9300 ?
  C8 C9 . 1.364(6) ?
  C8 H8 . 0.9300 ?
  C9 C10 . 1.383(6) ?
  C9 C13 . 1.480(6) ?
  C10 C11 . 1.374(5) ?
  C10 H10 . 0.9300 ?
  C11 H11 . 0.9300 ?
  C12 H12A . 0.9600 ?
  C12 H12B . 0.9600 ?
  C12 H12C . 0.9600 ?
  C13 H13A . 0.9600 ?
  C13 H13B . 0.9600 ?
  C13 H13C . 0.9600 ?
  C14 N4 . 1.319(4) yes
  C14 N3 . 1.326(4) yes
  N3 H3A . 0.8600 ?
  N3 H3B . 0.8600 ?
  N4 H4C . 0.8600 ?
  N4 H4D . 0.8600 ?
  C15 O2 . 1.240(4) ?
  C15 O1 . 1.245(4) ?
  C15 C16 . 1.492(5) ?
  C16 H16A . 0.9600 ?
  C16 H16B . 0.9600 ?
  C16 H16C . 0.9600 ?
  C17 O3 . 1.252(9) ?
  C17 C18 2 1.395(6) ?
  C17 C18 . 1.395(6) ?
  C18 H18A . 0.9600 ?
  C18 H18B . 0.9600 ?
  C18 H18C . 0.9600 ?
_cod_database_code 2012810