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4-[N-(2-Chloro-6-methyl­phen­yl)ureido]pyridinium chloride, C13H13ClN3O+·Cl- (CI-953 hydro­chloride), crystallizes with Z' = 2 in P\overline{1}. In both mol­ecules, the methyl groups and Cl atoms on the benzene rings are disordered. The benzene rings of mol­ecules A and B adopt two conformations, differing by a rotation of 180° about the C-N bond to the ureido group, in an approximate 1:1 ratio. This disorder is further enhanced by the rotation of the methyl groups in both adopted positions. The pyridine and benzene rings inter­sect at angles of 102.1 (1) and 111.3 (1)° for A and B, respectively. Hydrogen bonding is mediated by Cl- anions, resulting in indirect connectivity between the mol­ecules. Superposition of the mol­ecular structure, after 180° rotation about an amide bond, with that of phenytoin shows that the chemically different mol­ecules possess stereochemical features in common, which may explain their common activities.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106005543/gd1429sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106005543/gd1429Isup2.hkl
Contains datablock I

CCDC reference: 605687

Comment top

N-Phenyl-N'-pyridinylureas were shown (Lobbestael et al., 1986) to possess anticonvulsant activity in the NIH–NINCDS Antiepileptic Drug Discovery Program. Subsequently, synthesis and testing of a series of over 50 substituted derivatives (Pavia et al., 1990) led to identification of N-(2-chloro-6-methylphenyl)-N'-pyridin-4-ylurea (CI-953) as having the most desirable in vivo profile for a potential anticonvulsant drug. The overall pharmaceutical effects of CI-953 in animal models were similar qualitatively and quantitatively to those of the well known antiepileptic drug phenytoin. These pharmacological similarities led us to determine the crystal and conformational structures of CI-953 in order to ascertain if it possessed stereochemical features in common with the chemically different drug phenytoin, which might be responsible for their similar anticonvulsant properties.

CI-953 hydrochloride crystallizes with Z' = 2 (Fig. 1). The two independent molecules have similar conformations with approximately planar pyridinylurea fragments intersecting the 2,6-disubstituted phenyl ring planes at angles of 69 and 78°. The phenyl rings in both molecules exist in two possible conformations differing by 180° rotation about the C3—N8 bond, resulting in positional disorder of the ortho Cl atoms and methyl groups, with each occupying 50% of each position in the crystal structure. This disorder is further augmented by rotational disorder of the methyl group's H atoms in both positions. Protonation occurs at the pyridinyl atom N15 in both independent molecules. As shown in Fig. 1, the two CI-953 molecules are indirectly linked through hydrogen bonds (Table 1) from the two urea imine groups in each to a chloride anion, a strong intermolecular interaction made possible by/resulting in the cis conformation of the imine H atoms (Fig.2). In addition, a C—H···O hydrogen bond links the type A molecules (Table 1). Van der Waals interactions also contribute to the crystal packing. Intramolecular bond distances and angles are consistent with normal values.

Stereochemical features common to several chemically different types of anticonvulsant drugs, and which are likely determinants of their antiepileptic activity, have been established (Camerman & Camerman, 1980). They consist of two electronegative atoms (hydrogen-bond acceptors) approximately 4.5–5.5 Å apart and at least one hydrophobic group (phenyl ring or equivalent) at a particular location and orientation relative to those atoms. These findings are further supported by a recent study (Thenmozhiyal et al., 2004) of the anticonvulsant properties of a series of phenylmethylenehydantoins, which found that the most important structure–activity descriptor, in essence, was the molecular electronegativity or electron donor capabilities. Although CI-953 is chemically very different from the other drugs studied, we have investigated through molecular superpositions whether similar stereochemical features could exist in CI-953.

Superpositions of CI-953 with phenytoin (Camerman & Camerman, 1971), the best known and conformationally most rigid of the anticonvulsants, maximizing the fit of the two most electronegative atoms, the carbonyl atom O10 and the pyridinal atom N15, with the carbonyl O atoms of phenytoin did not result in a fit of the substituted phenyl group of CI-953 with a phenyl ring of phenytoin even if allowable phenyl ring rotations were invoked. However, as noted above, the observed CI-953 molecular conformation has cis imine H atoms, a conformation favored because of intermolecular hydrogen bonding to the chloride ions. In the absence of this crystallographically imposed feature, a molecular conformation featuring a trans relation of the urea imine H atoms would also be plausible. Accordingly, we produced that conformation by a rotation of 180° about the N8—C9 bond. We then superposed this CI-953 structure with phenytoin by a least-squares maximization of the fit of three atoms in each molecule: O10 and N15 in CI-953 with the carbonyl O atoms in phenytoin, and a phenyl C atom in each (C5 in CI-953 and C11 in phenytoin). The results are shown stereoscopically in Fig. 3. Despite their differences in chemical structure, the two electronegative atoms in each molecule occupy similar positions in space and the disubstituted phenyl ring of CI-953 has a similar position and orientation to a phenyl ring of phenytoin. Since these features are the mediators of anticonvulsant activity in phenytoin, the stereochemical results presented here are persuasive evidence that these features are responsible for the similar anticonvulsant effects of CI-953, and that the two drugs likely involve very similar mechanisms.

It is also noteworthy that in the series of N-phenyl-N'-pyridinylureas synthesized and tested for anticonvulsant activity the most promising analogues, in addition to CI-953, were the 2,6-bismethylphenyl and 2,6-bischlorophenyl compounds. This suggest that the primary function of these groups is to ensure, through steric interactions, that the phenyl plane is roughly perpendicular to the plane of the rest of the molecule, thus maintaining an orientation similar to that of a phenyl ring in phenytoin. The small size of the substituents is also necessary to limit the overall size of the hydrophobic entity in this position.

The efficacy of many antiepileptic drugs is attributed to interactions with ion channels or neurotransmitter systems (Malawska, 2005) but their therapeutic mechanisms at the molecular level are not well understood. Although broad classification of drugs into categories based on a particular mechanistic system is possible, this has limited value because most anticonvulsants possess more than one mechanism of action. The identification of common stereochemical features in chemically different anticonvulsant molecules facilitates new drug design independent of the mechanism(s) of action.

Experimental top

Crystals suitable for data collection were obtained by dissolving CI-953 in methanol and subsequently subjected to slow evaporation. Crystals grew in about three weeks. The crystals were small colourless needles. Attempts to grow better crystals in order to avoid disorder proved unsuccessful.

Refinement top

All H atoms, except those of the methyl groups, were initially located on a difference map and well behaving during refinement, however, low data to parameters ratio justified placement of H atoms in calculated positions in a riding model approximation. An overall isotropic temperature displacement parameter was refined for all H atoms except for the methyl groups. The final Uiso=0.08 (3) Å2 and the range of distances 0.86–0.93 Å. The H atoms from methyl groups were refined as idealized disordered groups with two positions rotated from each other by 60° and the methyl groups C atoms and Cl atoms were refined with partial occupancies set to sum to unity. The C—H distances were fixed at 1.0 Å.

Computing details top

Data collection: Picker Operating Manual (Picker, 1967); cell refinement: Picker Operating Manual; data reduction: DATRDN (Stewart, 1976); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular structure of CI-953, showing 50% probability displacement ellipsoids. H atoms are drawn as small circles of arbitrary radii.
[Figure 2] Fig. 2. A stereodiagram of the molecular packing and hydrogen-bond scheme. Atoms are drawn as circles of arbitrary radii. For clarity, only the H atoms participating in hydrogen bonding are shown.
[Figure 3] Fig. 3. A stereodiagram of the superposition of rotated CI-953 (filled bonds, small circles) and phenytoin. Electronegative atoms are labeled (O is oxygen, N is nitrogen).
4-[N-(2-Chloro-6-methylphenyl)ureido]pyridinium chloride top
Crystal data top
C13H13ClN3O+·ClZ = 4
Mr = 298.16F(000) = 616
Triclinic, P1Dx = 1.371 Mg m3
a = 8.022 (3) ÅCu Kα radiation, λ = 1.54178 Å
b = 13.193 (4) ÅCell parameters from 32 reflections
c = 14.893 (4) Åθ = 19–45°
α = 69.06 (3)°µ = 4.01 mm1
β = 81.29 (2)°T = 294 K
γ = 80.60 (3)°Needle, colourless
V = 1444.9 (9) Å30.52 × 0.12 × 0.08 mm
Data collection top
Picker FACS-1 four-circle
diffractometer
3375 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.005
Ni-filtered radiation monochromatorθmax = 60.0°, θmin = 3.2°
θ/2θ scansh = 49
Absorption correction: ψ scan
(North et al., 1968)
k = 1414
Tmin = 0.586, Tmax = 0.724l = 1616
4418 measured reflections3 standard reflections every 100 reflections
4272 independent reflections intensity decay: 2.7%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.134 w = 1/[σ2(Fo2) + (0.0837P)2 + 0.3467P]
where P = (Fo2 + 2Fc2)/3
S = 0.94(Δ/σ)max = 0.003
4272 reflectionsΔρmax = 0.27 e Å3
385 parametersΔρmin = 0.15 e Å3
7 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0062 (6)
Crystal data top
C13H13ClN3O+·Clγ = 80.60 (3)°
Mr = 298.16V = 1444.9 (9) Å3
Triclinic, P1Z = 4
a = 8.022 (3) ÅCu Kα radiation
b = 13.193 (4) ŵ = 4.01 mm1
c = 14.893 (4) ÅT = 294 K
α = 69.06 (3)°0.52 × 0.12 × 0.08 mm
β = 81.29 (2)°
Data collection top
Picker FACS-1 four-circle
diffractometer
3375 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.005
Tmin = 0.586, Tmax = 0.724θmax = 60.0°
4418 measured reflections3 standard reflections every 100 reflections
4272 independent reflections intensity decay: 2.7%
Refinement top
R[F2 > 2σ(F2)] = 0.0437 restraints
wR(F2) = 0.134H-atom parameters constrained
S = 0.94Δρmax = 0.27 e Å3
4272 reflectionsΔρmin = 0.15 e Å3
385 parameters
Special details top

Experimental. No observed reflections above 60°.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C1A0.1968 (5)0.4567 (3)0.0898 (3)0.0664 (9)
H1A0.31260.47600.09500.081 (4)*
C2A0.1406 (5)0.3730 (2)0.0096 (2)0.0564 (8)
C3A0.0313 (4)0.3437 (2)0.0020 (2)0.0489 (7)
C4A0.1474 (5)0.4004 (2)0.0743 (2)0.0575 (8)
C5A0.0879 (6)0.4843 (3)0.1535 (2)0.0696 (10)
H5A0.16460.52310.20190.081 (4)*
C6A0.0831 (6)0.5110 (3)0.1614 (3)0.0703 (10)
H6A0.12150.56640.21580.081 (4)*
C7A0.344 (2)0.3784 (18)0.078 (3)0.047 (4)0.419 (6)
H7A10.37700.31690.01870.114 (16)*0.209 (3)
H7A20.39050.44560.08170.114 (16)*0.209 (3)
H7A30.39060.35830.13650.114 (16)*0.209 (3)
H7A40.39510.43030.13930.114 (16)*0.209 (3)
H7A50.38160.30160.07620.114 (16)*0.209 (3)
H7A60.38150.38890.02140.114 (16)*0.209 (3)
Cl7A0.3601 (7)0.3663 (5)0.0628 (6)0.093 (2)0.581 (6)
N8A0.0919 (4)0.25512 (19)0.07822 (19)0.0569 (7)
H8A0.13300.26800.12260.081 (4)*
C9A0.0852 (4)0.1504 (2)0.0853 (2)0.0470 (7)
O10A0.0297 (3)0.12564 (17)0.02623 (16)0.0662 (7)
N11A0.1474 (3)0.07603 (18)0.16927 (17)0.0486 (6)
H11A0.18260.10350.20630.081 (4)*
C12A0.1596 (4)0.0351 (2)0.2002 (2)0.0455 (7)
C13A0.1199 (5)0.0949 (2)0.1476 (2)0.0581 (8)
H13A0.08190.05960.08680.081 (4)*
C14A0.1377 (5)0.2058 (3)0.1867 (3)0.0698 (10)
H14A0.10940.24610.15230.081 (4)*
N15A0.1941 (4)0.2580 (2)0.2723 (2)0.0667 (8)
H15A0.20500.32820.29470.081 (4)*
C16A0.2343 (5)0.2035 (3)0.3240 (3)0.0647 (9)
H16A0.27360.24180.38410.081 (4)*
C17A0.2187 (4)0.0931 (2)0.2905 (2)0.0572 (8)
H17A0.24720.05570.32740.081 (4)*
C18A0.274 (3)0.3075 (17)0.0658 (17)0.107 (11)0.581 (6)
H18A0.21550.25100.12010.114 (16)*0.291 (3)
H18B0.33510.27080.03450.114 (16)*0.291 (3)
H18C0.35720.35830.09130.114 (16)*0.291 (3)
H18D0.38960.33570.04380.114 (16)*0.291 (3)
H18E0.27010.31600.12950.114 (16)*0.291 (3)
H18F0.24800.22850.07260.114 (16)*0.291 (3)
Cl1A0.2849 (11)0.3131 (6)0.0812 (7)0.0863 (17)0.419 (6)
C1B0.7192 (6)0.2579 (3)0.3600 (3)0.0815 (12)
H1B0.74110.31910.41420.080 (4)*
C2B0.6887 (4)0.1550 (3)0.3675 (3)0.0580 (8)
C3B0.6620 (4)0.0630 (2)0.2857 (2)0.0469 (7)
C4B0.6565 (5)0.0767 (3)0.1978 (2)0.0591 (8)
C5B0.6860 (6)0.1799 (3)0.1924 (3)0.0827 (12)
H5B0.68490.18920.13350.080 (4)*
C6B0.7171 (7)0.2696 (3)0.2731 (4)0.0952 (15)
H6B0.73690.33900.26820.080 (4)*
C7B0.638 (3)0.0211 (16)0.1086 (14)0.122 (11)0.603 (5)
H7B10.61170.08860.12660.114 (16)*0.301 (3)
H7B20.54360.01540.07450.114 (16)*0.301 (3)
H7B30.74640.02490.06500.114 (16)*0.301 (3)
H7B40.65610.00260.05080.114 (16)*0.301 (3)
H7B50.72420.07060.10290.114 (16)*0.301 (3)
H7B60.52140.06100.11240.114 (16)*0.301 (3)
Cl7B0.6024 (11)0.0360 (5)0.0992 (4)0.0797 (13)0.397 (5)
N8B0.6264 (3)0.04257 (19)0.29224 (18)0.0487 (6)
H8B0.53120.08010.27500.080 (4)*
C9B0.7349 (4)0.0884 (2)0.3244 (2)0.0462 (7)
O10B0.8778 (3)0.05029 (18)0.34184 (19)0.0645 (6)
N11B0.6573 (3)0.18678 (19)0.33408 (18)0.0479 (6)
H11B0.55490.20700.31870.080 (4)*
C12B0.7257 (4)0.2544 (2)0.3652 (2)0.0432 (6)
C13B0.8944 (4)0.2432 (3)0.3830 (2)0.0554 (8)
H13B0.96990.18480.37520.080 (4)*
C14B0.9480 (5)0.3176 (3)0.4116 (3)0.0672 (10)
H14B1.06180.31110.42100.080 (4)*
N15B0.8428 (4)0.3992 (2)0.4266 (2)0.0659 (8)
H15B0.88000.44430.44640.080 (4)*
C16B0.6799 (5)0.4130 (3)0.4116 (2)0.0612 (9)
H16B0.60800.47070.42350.080 (4)*
C17B0.6170 (4)0.3442 (2)0.3791 (2)0.0501 (7)
H17B0.50420.35610.36620.080 (4)*
C18B0.701 (4)0.144 (3)0.466 (2)0.074 (11)0.397 (5)
H18G0.67520.06550.46080.114 (16)*0.199 (3)
H18H0.81900.17190.48540.114 (16)*0.199 (3)
H18I0.61820.18780.51610.114 (16)*0.199 (3)
H18J0.73310.21790.51410.114 (16)*0.199 (3)
H18K0.58930.11160.48950.114 (16)*0.199 (3)
H18L0.79000.09560.45870.114 (16)*0.199 (3)
Cl1B0.6720 (9)0.1409 (5)0.4801 (5)0.0761 (14)0.603 (5)
Cl10.78591 (10)0.49808 (6)0.59447 (6)0.0552 (3)
Cl20.29829 (10)0.21846 (6)0.26294 (6)0.0625 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.076 (2)0.0475 (19)0.069 (2)0.0088 (17)0.0277 (19)0.0109 (18)
C2A0.071 (2)0.0387 (16)0.0548 (19)0.0076 (15)0.0162 (17)0.0057 (14)
C3A0.071 (2)0.0302 (14)0.0454 (16)0.0068 (14)0.0215 (15)0.0060 (13)
C4A0.076 (2)0.0391 (16)0.0567 (19)0.0111 (15)0.0050 (16)0.0145 (15)
C5A0.108 (3)0.0444 (18)0.0493 (19)0.020 (2)0.0040 (19)0.0076 (16)
C6A0.107 (3)0.0410 (18)0.053 (2)0.0070 (19)0.026 (2)0.0031 (16)
C7A0.050 (8)0.026 (5)0.075 (10)0.005 (5)0.009 (7)0.027 (6)
Cl7A0.070 (2)0.100 (4)0.114 (4)0.0141 (17)0.0103 (19)0.039 (2)
N8A0.087 (2)0.0320 (13)0.0536 (15)0.0050 (12)0.0352 (14)0.0059 (11)
C9A0.0598 (18)0.0332 (15)0.0455 (16)0.0043 (13)0.0117 (14)0.0085 (13)
O10A0.109 (2)0.0392 (11)0.0547 (13)0.0073 (12)0.0369 (13)0.0099 (10)
N11A0.0670 (16)0.0341 (13)0.0424 (13)0.0040 (11)0.0207 (12)0.0053 (11)
C12A0.0493 (17)0.0355 (15)0.0440 (16)0.0013 (12)0.0051 (13)0.0059 (12)
C13A0.079 (2)0.0371 (16)0.0561 (19)0.0065 (15)0.0182 (17)0.0091 (14)
C14A0.094 (3)0.0395 (17)0.076 (2)0.0062 (17)0.023 (2)0.0149 (17)
N15A0.080 (2)0.0331 (14)0.075 (2)0.0024 (13)0.0101 (16)0.0037 (14)
C16A0.079 (2)0.0450 (18)0.0520 (19)0.0008 (16)0.0153 (17)0.0053 (15)
C17A0.073 (2)0.0398 (17)0.0489 (18)0.0022 (15)0.0163 (16)0.0016 (14)
C18A0.063 (9)0.113 (15)0.121 (18)0.011 (8)0.033 (10)0.013 (10)
Cl1A0.095 (4)0.072 (3)0.077 (2)0.031 (2)0.004 (2)0.003 (2)
C1B0.103 (3)0.0385 (19)0.092 (3)0.0078 (19)0.003 (2)0.0125 (19)
C2B0.064 (2)0.0428 (17)0.065 (2)0.0061 (15)0.0063 (16)0.0158 (16)
C3B0.0503 (17)0.0332 (15)0.0563 (18)0.0079 (12)0.0013 (13)0.0156 (14)
C4B0.074 (2)0.0481 (18)0.0564 (19)0.0160 (16)0.0026 (16)0.0193 (16)
C5B0.115 (3)0.066 (2)0.082 (3)0.028 (2)0.017 (2)0.046 (2)
C6B0.140 (4)0.043 (2)0.104 (4)0.016 (2)0.012 (3)0.034 (2)
C7B0.143 (14)0.123 (13)0.113 (13)0.006 (7)0.009 (7)0.065 (9)
Cl7B0.118 (3)0.075 (2)0.0488 (17)0.034 (2)0.0102 (18)0.0130 (15)
N8B0.0533 (15)0.0362 (13)0.0603 (15)0.0011 (11)0.0142 (12)0.0193 (11)
C9B0.0492 (18)0.0393 (15)0.0480 (17)0.0058 (13)0.0012 (13)0.0134 (13)
O10B0.0449 (13)0.0576 (14)0.0969 (18)0.0020 (11)0.0106 (12)0.0358 (13)
N11B0.0440 (13)0.0425 (13)0.0625 (16)0.0035 (11)0.0072 (11)0.0243 (12)
C12B0.0477 (16)0.0366 (15)0.0442 (15)0.0122 (12)0.0030 (12)0.0102 (12)
C13B0.0522 (18)0.0456 (17)0.072 (2)0.0072 (14)0.0110 (15)0.0214 (16)
C14B0.068 (2)0.056 (2)0.080 (2)0.0149 (18)0.0260 (19)0.0154 (18)
N15B0.093 (2)0.0441 (15)0.0686 (18)0.0205 (15)0.0270 (16)0.0161 (14)
C16B0.084 (3)0.0380 (17)0.060 (2)0.0058 (16)0.0060 (18)0.0154 (15)
C17B0.0573 (19)0.0385 (16)0.0538 (17)0.0082 (13)0.0029 (14)0.0148 (14)
C18B0.060 (10)0.051 (10)0.09 (2)0.009 (7)0.029 (14)0.009 (11)
Cl1B0.107 (3)0.0648 (19)0.0493 (12)0.0180 (18)0.0004 (16)0.0107 (11)
Cl10.0700 (5)0.0341 (4)0.0603 (5)0.0074 (3)0.0128 (4)0.0115 (3)
Cl20.0624 (5)0.0558 (5)0.0780 (6)0.0086 (4)0.0341 (4)0.0292 (4)
Geometric parameters (Å, º) top
C1A—C6A1.362 (6)C1B—C6B1.360 (6)
C1A—C2A1.381 (5)C1B—C2B1.381 (5)
C1A—H1A0.9300C1B—H1B0.9300
C2A—C3A1.381 (5)C2B—C3B1.393 (5)
C2A—C18A1.55 (2)C2B—C18B1.55 (3)
C2A—Cl1A1.689 (8)C2B—Cl1B1.735 (6)
C3A—C4A1.391 (5)C3B—C4B1.393 (4)
C3A—N8A1.422 (4)C3B—N8B1.410 (3)
C4A—C5A1.381 (5)C4B—C5B1.372 (5)
C4A—C7A1.551 (18)C4B—C7B1.491 (19)
C4A—Cl7A1.711 (7)C4B—Cl7B1.726 (7)
C5A—C6A1.372 (6)C5B—C6B1.372 (6)
C5A—H5A0.9300C5B—H5B0.9300
C6A—H6A0.9300C6B—H6B0.9300
C7A—H7A11.0000C7B—H7B11.0000
C7A—H7A21.0000C7B—H7B21.0000
C7A—H7A31.0000C7B—H7B31.0000
C7A—H7A41.0000C7B—H7B41.0000
C7A—H7A51.0000C7B—H7B51.0000
C7A—H7A61.0000C7B—H7B61.0000
N8A—C9A1.356 (4)N8B—C9B1.362 (4)
N8A—H8A0.8600N8B—H8B0.8600
C9A—O10A1.204 (3)C9B—O10B1.201 (4)
C9A—O10A1.204 (3)C9B—O10B1.201 (4)
C9A—N11A1.389 (4)C9B—N11B1.392 (4)
N11A—C12A1.362 (4)N11B—C12B1.357 (4)
N11A—H11A0.8600N11B—H11B0.8600
C12A—C13A1.392 (4)C12B—C13B1.393 (4)
C12A—C17A1.400 (4)C12B—C17B1.411 (4)
C13A—C14A1.360 (5)C13B—C14B1.349 (4)
C13A—H13A0.9300C13B—H13B0.9300
C14A—N15A1.323 (5)C14B—N15B1.319 (5)
C14A—H14A0.9300C14B—H14B0.9300
N15A—C16A1.327 (5)N15B—C16B1.331 (5)
N15A—H15A0.8600N15B—H15B0.8600
C16A—C17A1.352 (4)C16B—C17B1.361 (4)
C16A—H16A0.9300C16B—H16B0.9300
C17A—H17A0.9300C17B—H17B0.9300
C18A—H18A1.0000C18B—H18G1.0000
C18A—H18B1.0000C18B—H18H1.0000
C18A—H18C1.0000C18B—H18I1.0000
C18A—H18D1.0000C18B—H18J1.0000
C18A—H18E1.0000C18B—H18K1.0000
C18A—H18F1.0000C18B—H18L1.0000
C6A—C1A—C2A120.2 (4)C6B—C1B—C2B119.9 (4)
C6A—C1A—H1A119.9C6B—C1B—H1B120.1
C2A—C1A—H1A119.9C2B—C1B—H1B120.1
C1A—C2A—C3A120.0 (3)C1B—C2B—C3B120.2 (3)
C1A—C2A—C18A118.3 (8)C1B—C2B—C18B118.5 (12)
C3A—C2A—C18A121.4 (8)C3B—C2B—C18B121.1 (12)
C1A—C2A—Cl1A118.9 (4)C1B—C2B—Cl1B119.9 (4)
C3A—C2A—Cl1A120.9 (4)C3B—C2B—Cl1B119.9 (3)
C2A—C3A—C4A119.8 (3)C2B—C3B—C4B119.1 (3)
C2A—C3A—N8A120.9 (3)C2B—C3B—N8B121.1 (3)
C4A—C3A—N8A119.3 (3)C4B—C3B—N8B119.6 (3)
C5A—C4A—C3A119.1 (3)C5B—C4B—C3B119.5 (3)
C5A—C4A—C7A114.1 (13)C5B—C4B—C7B120.6 (9)
C3A—C4A—C7A126.8 (13)C3B—C4B—C7B119.6 (9)
C5A—C4A—Cl7A121.4 (4)C5B—C4B—Cl7B121.3 (4)
C3A—C4A—Cl7A119.5 (4)C3B—C4B—Cl7B119.1 (3)
C6A—C5A—C4A120.7 (3)C6B—C5B—C4B120.7 (4)
C6A—C5A—H5A119.7C6B—C5B—H5B119.6
C4A—C5A—H5A119.7C4B—C5B—H5B119.6
C1A—C6A—C5A120.3 (3)C1B—C6B—C5B120.6 (3)
C1A—C6A—H6A119.9C1B—C6B—H6B119.7
C5A—C6A—H6A119.9C5B—C6B—H6B119.7
C4A—C7A—H7A1109.5C4B—C7B—H7B1109.5
C4A—C7A—H7A2109.5C4B—C7B—H7B2109.5
H7A1—C7A—H7A2109.5H7B1—C7B—H7B2109.5
C4A—C7A—H7A3109.5C4B—C7B—H7B3109.5
H7A1—C7A—H7A3109.5H7B1—C7B—H7B3109.5
H7A2—C7A—H7A3109.5H7B2—C7B—H7B3109.5
C4A—C7A—H7A4109.5C4B—C7B—H7B4109.5
H7A1—C7A—H7A4141.1H7B1—C7B—H7B4141.1
H7A2—C7A—H7A456.3H7B2—C7B—H7B456.3
H7A3—C7A—H7A456.3H7B3—C7B—H7B456.3
C4A—C7A—H7A5109.5C4B—C7B—H7B5109.5
H7A1—C7A—H7A556.3H7B1—C7B—H7B556.3
H7A2—C7A—H7A5141.1H7B2—C7B—H7B5141.1
H7A3—C7A—H7A556.3H7B3—C7B—H7B556.3
H7A4—C7A—H7A5109.5H7B4—C7B—H7B5109.5
C4A—C7A—H7A6109.5C4B—C7B—H7B6109.5
H7A1—C7A—H7A656.3H7B1—C7B—H7B656.3
H7A2—C7A—H7A656.3H7B2—C7B—H7B656.3
H7A3—C7A—H7A6141.1H7B3—C7B—H7B6141.1
H7A4—C7A—H7A6109.5H7B4—C7B—H7B6109.5
H7A5—C7A—H7A6109.5H7B5—C7B—H7B6109.5
C9A—N8A—C3A120.5 (2)C9B—N8B—C3B123.5 (3)
C9A—N8A—H8A119.8C9B—N8B—H8B118.3
C3A—N8A—H8A119.8C3B—N8B—H8B118.3
O10A—C9A—N8A123.8 (3)O10B—C9B—N8B125.4 (3)
O10A—C9A—N8A123.8 (3)O10B—C9B—N8B125.4 (3)
O10A—C9A—N11A124.4 (3)O10B—C9B—N11B124.2 (3)
O10A—C9A—N11A124.4 (3)O10B—C9B—N11B124.2 (3)
N8A—C9A—N11A111.8 (2)N8B—C9B—N11B110.4 (3)
C12A—N11A—C9A128.0 (2)C12B—N11B—C9B127.0 (3)
C12A—N11A—H11A116.0C12B—N11B—H11B116.5
C9A—N11A—H11A116.0C9B—N11B—H11B116.5
N11A—C12A—C13A124.6 (3)N11B—C12B—C13B125.4 (3)
N11A—C12A—C17A117.6 (3)N11B—C12B—C17B117.0 (3)
C13A—C12A—C17A117.8 (3)C13B—C12B—C17B117.5 (3)
C14A—C13A—C12A118.8 (3)C14B—C13B—C12B119.7 (3)
C14A—C13A—H13A120.6C14B—C13B—H13B120.1
C12A—C13A—H13A120.6C12B—C13B—H13B120.1
N15A—C14A—C13A121.7 (3)N15B—C14B—C13B121.6 (3)
N15A—C14A—H14A119.1N15B—C14B—H14B119.2
C13A—C14A—H14A119.1C13B—C14B—H14B119.2
C14A—N15A—C16A121.0 (3)C14B—N15B—C16B121.1 (3)
C14A—N15A—H15A119.5C14B—N15B—H15B119.4
C16A—N15A—H15A119.5C16B—N15B—H15B119.4
N15A—C16A—C17A120.8 (3)N15B—C16B—C17B121.1 (3)
N15A—C16A—H16A119.6N15B—C16B—H16B119.5
C17A—C16A—H16A119.6C17B—C16B—H16B119.5
C16A—C17A—C12A119.8 (3)C16B—C17B—C12B118.9 (3)
C16A—C17A—H17A120.1C16B—C17B—H17B120.5
C12A—C17A—H17A120.1C12B—C17B—H17B120.5
C2A—C18A—H18A109.5C2B—C18B—H18G109.5
C2A—C18A—H18B109.5C2B—C18B—H18H109.5
H18A—C18A—H18B109.5H18G—C18B—H18H109.5
C2A—C18A—H18C109.5C2B—C18B—H18I109.5
H18A—C18A—H18C109.5H18G—C18B—H18I109.5
H18B—C18A—H18C109.5H18H—C18B—H18I109.5
C2A—C18A—H18D109.5C2B—C18B—H18J109.5
H18A—C18A—H18D141.1H18G—C18B—H18J141.1
H18B—C18A—H18D56.3H18H—C18B—H18J56.3
H18C—C18A—H18D56.3H18I—C18B—H18J56.3
C2A—C18A—H18E109.5C2B—C18B—H18K109.5
H18A—C18A—H18E56.3H18G—C18B—H18K56.3
H18B—C18A—H18E141.1H18H—C18B—H18K141.1
H18C—C18A—H18E56.3H18I—C18B—H18K56.3
H18D—C18A—H18E109.5H18J—C18B—H18K109.5
C2A—C18A—H18F109.5C2B—C18B—H18L109.5
H18A—C18A—H18F56.3H18G—C18B—H18L56.3
H18B—C18A—H18F56.3H18H—C18B—H18L56.3
H18C—C18A—H18F141.1H18I—C18B—H18L141.1
H18D—C18A—H18F109.5H18J—C18B—H18L109.5
H18E—C18A—H18F109.5H18K—C18B—H18L109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N8A—H8A···Cl20.862.483.273 (3)154
N8B—H8B···Cl20.862.373.183 (3)158
N11A—H11A···Cl20.862.343.173 (3)163
N11B—H11B···Cl20.862.303.131 (3)164
N15A—H15A···Cl1i0.862.263.072 (3)158
N15B—H15B···Cl10.862.533.155 (3)131
N15B—H15B···Cl1ii0.862.823.397 (3)126
C13A—H13A···O10A0.932.272.864 (4)121
C13A—H13A···O10Aiii0.932.483.186 (4)133
C13B—H13B···O10B0.932.262.850 (4)121
Symmetry codes: (i) x+1, y, z+1; (ii) x+2, y+1, z+1; (iii) x, y, z.

Experimental details

Crystal data
Chemical formulaC13H13ClN3O+·Cl
Mr298.16
Crystal system, space groupTriclinic, P1
Temperature (K)294
a, b, c (Å)8.022 (3), 13.193 (4), 14.893 (4)
α, β, γ (°)69.06 (3), 81.29 (2), 80.60 (3)
V3)1444.9 (9)
Z4
Radiation typeCu Kα
µ (mm1)4.01
Crystal size (mm)0.52 × 0.12 × 0.08
Data collection
DiffractometerPicker FACS-1 four-circle
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.586, 0.724
No. of measured, independent and
observed [I > 2σ(I)] reflections
4418, 4272, 3375
Rint0.005
θmax (°)60.0
(sin θ/λ)max1)0.562
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.134, 0.94
No. of reflections4272
No. of parameters385
No. of restraints7
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.15

Computer programs: Picker Operating Manual (Picker, 1967), Picker Operating Manual, DATRDN (Stewart, 1976), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N8A—H8A···Cl20.862.483.273 (3)154
N8B—H8B···Cl20.862.373.183 (3)158
N11A—H11A···Cl20.862.343.173 (3)163
N11B—H11B···Cl20.862.303.131 (3)164
N15A—H15A···Cl1i0.862.263.072 (3)158
N15B—H15B···Cl10.862.533.155 (3)131
N15B—H15B···Cl1ii0.862.823.397 (3)126
C13A—H13A···O10A0.932.272.864 (4)121
C13A—H13A···O10Aiii0.932.483.186 (4)133
C13B—H13B···O10B0.932.262.850 (4)121
Symmetry codes: (i) x+1, y, z+1; (ii) x+2, y+1, z+1; (iii) x, y, z.
 

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