#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/4101241.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_4101241
_journal_name_full  'Journal of the American Chemical Society'
_journal_year       2006
_publ_section_title
;
'What is syncrystallization? States of the pH indicator methyl red
in crystals of phthalic acid'
;
loop_
_publ_author_name
'Jason B. Benedict'
'Dawn E. Cohen'
'Scott Lovell'
'Andrew L. Rohl'
'Bart Kahr'
_chemical_name_common  'methyl red'
_chemical_formula_moiety  'C15 H15 N3 O2'
_chemical_formula_sum   'C15 H15 N3 O2'
_chemical_formula_weight  269.30
_symmetry_space_group_name_H-M 'P -1'
_symmetry_cell_setting 'triclinic'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number  2
loop_
_symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, -z'
_cell_length_a  8.2370(5)
_cell_length_b  8.4990(6)
_cell_length_c  11.2110(10)
_cell_angle_alpha  92.478(3)
_cell_angle_beta  110.281(3)
_cell_angle_gamma  113.705(3)
_cell_volume  658.66(9)
_cell_formula_units_Z  2
_cell_measurement_temperature  130(2)
_exptl_crystal_density_diffrn  1.358
_diffrn_ambient_temperature  130(2)
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2489(2) 0.4723(2) 0.64239(16) 0.0450(5) Uani 1 1 d . . .
H1 H 0.2039 0.3884 0.5795 0.068 Uiso 1 1 calc R . .
O2 O 0.5284(2) 0.6368(2) 0.80482(17) 0.0520(5) Uani 1 1 d . . .
N1 N 0.2280(3) 0.2321(2) 0.48019(18) 0.0357(5) Uani 1 1 d . . .
N2 N 0.1452(3) 0.0952(2) 0.38920(18) 0.0385(5) Uani 1 1 d . . .
N3 N -0.6380(3) -0.1727(3) 0.07652(19) 0.0439(6) Uani 1 1 d . . .
C1 C 0.4368(4) 0.5216(3) 0.7072(2) 0.0400(6) Uani 1 1 d . . .
C2 C 0.5303(3) 0.4310(3) 0.6557(2) 0.0336(6) Uani 1 1 d . . .
C3 C 0.7292(3) 0.4945(3) 0.7216(2) 0.0386(6) Uani 1 1 d . . .
H3 H 0.7983 0.5925 0.7929 0.046 Uiso 1 1 calc R . .
C4 C 0.8274(3) 0.4161(3) 0.6842(2) 0.0405(6) Uani 1 1 d . . .
H4 H 0.9634 0.4608 0.7293 0.049 Uiso 1 1 calc R . .
C5 C 0.7269(4) 0.2722(3) 0.5809(2) 0.0416(6) Uani 1 1 d . . .
H5 H 0.7933 0.2159 0.5568 0.050 Uiso 1 1 calc R . .
C6 C 0.5311(3) 0.2110(3) 0.5134(2) 0.0391(6) Uani 1 1 d . . .
H6 H 0.4639 0.1147 0.4409 0.047 Uiso 1 1 calc R . .
C7 C 0.4295(3) 0.2879(3) 0.5495(2) 0.0332(6) Uani 1 1 d . . .
C8 C -0.0492(3) 0.0409(3) 0.3137(2) 0.0344(6) Uani 1 1 d . . .
C9 C -0.1423(3) -0.1179(3) 0.2227(2) 0.0396(6) Uani 1 1 d . . .
H9 H -0.0700 -0.1788 0.2162 0.048 Uiso 1 1 calc R . .
C10 C -0.3344(4) -0.1885(3) 0.1428(2) 0.0407(6) Uani 1 1 d . . .
H10 H -0.3926 -0.2956 0.0811 0.049 Uiso 1 1 calc R . .
C11 C -0.4463(3) -0.1025(3) 0.1517(2) 0.0367(6) Uani 1 1 d . . .
C12 C -0.3504(3) 0.0616(3) 0.2408(2) 0.0377(6) Uani 1 1 d . . .
H12 H -0.4210 0.1247 0.2462 0.045 Uiso 1 1 calc R . .
C13 C -0.1587(3) 0.1303(3) 0.3186(2) 0.0387(6) Uani 1 1 d . . .
H13 H -0.0979 0.2406 0.3772 0.046 Uiso 1 1 calc R . .
C14 C -0.7369(4) -0.3422(3) -0.0139(2) 0.0522(7) Uani 1 1 d . . .
H14A H -0.6828 -0.3343 -0.0800 0.078 Uiso 1 1 calc R . .
H14B H -0.8750 -0.3742 -0.0563 0.078 Uiso 1 1 calc R . .
H14C H -0.7192 -0.4320 0.0337 0.078 Uiso 1 1 calc R . .
C15 C -0.7559(4) -0.0887(4) 0.0905(3) 0.0533(7) Uani 1 1 d . . .
H15A H -0.7573 -0.0877 0.1776 0.080 Uiso 1 1 calc R . .
H15B H -0.8882 -0.1544 0.0249 0.080 Uiso 1 1 calc R . .
H15C H -0.7013 0.0323 0.0786 0.080 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0410(11) 0.0458(11) 0.0477(11) 0.0044(8) 0.0139(9) 0.0224(9)
O2 0.0508(12) 0.0488(11) 0.0505(11) -0.0064(9) 0.0124(10) 0.0248(9)
N1 0.0341(12) 0.0343(11) 0.0369(11) 0.0083(9) 0.0118(10) 0.0154(9)
N2 0.0365(13) 0.0334(11) 0.0422(12) 0.0064(10) 0.0152(10) 0.0128(10)
N3 0.0355(13) 0.0462(12) 0.0424(12) 0.0026(10) 0.0121(10) 0.0145(10)
C1 0.0423(16) 0.0330(14) 0.0452(15) 0.0096(12) 0.0163(13) 0.0180(12)
C2 0.0335(15) 0.0287(12) 0.0367(13) 0.0054(10) 0.0126(12) 0.0133(11)
C3 0.0365(15) 0.0362(14) 0.0382(14) 0.0049(11) 0.0121(12) 0.0144(11)
C4 0.0306(15) 0.0448(15) 0.0431(15) 0.0093(12) 0.0135(12) 0.0150(12)
C5 0.0391(16) 0.0450(14) 0.0425(14) 0.0049(12) 0.0148(12) 0.0222(12)
C6 0.0378(16) 0.0402(14) 0.0386(14) 0.0038(11) 0.0135(12) 0.0185(12)
C7 0.0321(15) 0.0341(13) 0.0336(13) 0.0103(10) 0.0134(11) 0.0144(11)
C8 0.0285(14) 0.0363(13) 0.0344(13) 0.0067(11) 0.0108(11) 0.0123(11)
C9 0.0396(16) 0.0357(14) 0.0440(15) 0.0051(11) 0.0184(13) 0.0160(12)
C10 0.0387(16) 0.0378(14) 0.0397(14) 0.0030(11) 0.0136(12) 0.0136(12)
C11 0.0302(14) 0.0383(13) 0.0375(14) 0.0100(11) 0.0123(12) 0.0122(11)
C12 0.0342(15) 0.0378(14) 0.0415(14) 0.0084(11) 0.0137(12) 0.0174(11)
C13 0.0376(15) 0.0340(14) 0.0418(15) 0.0030(11) 0.0167(12) 0.0130(12)
C14 0.0380(16) 0.0584(17) 0.0412(15) -0.0017(13) 0.0097(13) 0.0098(13)
C15 0.0393(16) 0.0622(18) 0.0599(18) 0.0130(14) 0.0166(14) 0.0265(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.331(3) . ?
O1 H1 0.8400 . ?
O2 C1 1.211(3) . ?
N1 N2 1.279(2) . ?
N1 C7 1.423(3) . ?
N2 C8 1.388(3) . ?
N3 C11 1.356(3) . ?
N3 C14 1.457(3) . ?
N3 C15 1.459(3) . ?
C1 C2 1.505(3) . ?
C2 C3 1.392(3) . ?
C2 C7 1.402(3) . ?
C3 C4 1.385(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.375(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(3) . ?
C6 H6 0.9500 . ?
C8 C9 1.399(3) . ?
C8 C13 1.406(3) . ?
C9 C10 1.369(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.411(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.419(3) . ?
C12 C13 1.362(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?