#------------------------------------------------------------------------------
#$Date: 2025-08-20 17:12:52 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301832 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/12/4101241.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
loop_
_publ_author_name
'Jason B. Benedict'
'Dawn E. Cohen'
'Scott Lovell'
'Andrew L. Rohl'
'Bart Kahr'
_publ_section_title
;
'What is syncrystallization? States of the pH indicator methyl red
in crystals of phthalic acid'
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/ja0601181
_journal_year                    2006
_chemical_formula_moiety         'C15 H15 N3 O2'
_chemical_formula_sum            'C15 H15 N3 O2'
_chemical_formula_weight         269.30
_chemical_name_common            'methyl red'
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                92.478(3)
_cell_angle_beta                 110.281(3)
_cell_angle_gamma                113.705(3)
_cell_formula_units_Z            2
_cell_length_a                   8.2370(5)
_cell_length_b                   8.4990(6)
_cell_length_c                   11.2110(10)
_cell_measurement_temperature    130(2)
_cell_volume                     658.66(9)
_diffrn_ambient_temperature      130(2)
_exptl_crystal_density_diffrn    1.358
_cod_database_code               4101241
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_
_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 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9881
2 PubChem 10303
