3-(4-Chloro­anilino)-2,5-dimethyl­cyclo­hex-2-en-1-one

North, H.; Wutoh, K.; Odoom, M.K.; Karla, P.; Scott, K.R.; Butcher, R.J.

doi:10.1107/S1600536811005678

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Pages o1283-o1284

doi:10.1107/S1600536811005678

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3-(4-Chloroanilino)-2,5-dimethylcyclohex-2-en-1-one

Henry North,^a Kwame Wutoh,^b M'egya K. Odoom,^c Pradeep Karla,^a Kenneth R. Scott ^a and Ray J. Butcher ^d ^*

^aDepartment of Pharmaceutical Sciences, Howard University, 2300 4th Street NW, Washington, DC 20059, USA, ^bBowie High School, Bowie, MD 20715, USA, ^cFork Union Military Academy, Fork Union, VA 23055, USA, and ^dDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
^*Correspondence e-mail: rbutcher99@yahoo.com

(Received 2 February 2011; accepted 15 February 2011; online 29 April 2011)

In the title compound, C₁₄H₁₆ClNO, the dihedral angle between the benzene ring and the conjugated part of the cyclohexene ring is 61.7 (2)°. Part of the cyclohexene ring and one of the attached methyl groups are disordered over two orientations with occupancies of 0.602 (7) and 0.398 (7). In addition, the crystal studied was a racemic twin [Flack parameter = 0.58 (4)]. In the crystal, the molecules are linked into chains in the b-axis direction by intermolecular N—H⋯O hydrogen bonds. C—H⋯O and C—H⋯Cl interactions are also observed.

Related literature

The title compound 3-(4-chlorophenylamino)-2,5-dimethylcyclohex-2-enone possesses significant anticonvulsant properties. For the anticonvulsant properties of enaminones, see: Edafiogho et al. (1992 ); Eddington et al. (2003 ); Scott et al. (1993 , 1995 ). For related structures see: Alexander et al. (2010 , 2011 ).

Experimental

Crystal data

C₁₄H₁₆ClNO
M_r = 249.73
Monoclinic, P 2₁
a = 6.0775 (5) Å
b = 8.8106 (5) Å
c = 12.5794 (7) Å
β = 99.904 (7)°
V = 663.5 (1) Å³
Z = 2
Cu Kα radiation
μ = 2.41 mm⁻¹
T = 295 K
0.45 × 0.28 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.679, T_max = 1.000
2292 measured reflections
1705 independent reflections
1417 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.150
S = 1.00
1705 reflections
171 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.17 e Å⁻³
Absolute structure: Flack (1983 ), 259 Friedel pairs
Flack parameter: 0.58 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	2.10	2.897 (4)	155
C6—H6A⋯O1ⁱⁱ	0.93	2.42	3.340 (4)	172
C12A—H12A⋯O1ⁱⁱ	0.97	2.58	3.439 (9)	147
C12B—H12D⋯Cl1ⁱⁱⁱ	0.97	2.95	3.79 (3)	146
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z]$ ; (iii) $[-x+2, y+{\script{1\over 2}}, -z+1]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811005678/hg2794sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811005678/hg2794Isup2.hkl

checkCIF report

Comment top

The study of enaminones has led to several compounds possessing anticonvulsant properties (Edafiogho et al., 1992; Eddington et al., 2003; Scott et al., 1993, 1995; Alexander et al., 2010, 2011). Our group has extensively studied the effects of modification of the enaminone with substitutions at the methyl ester, ethyl ester, and without the ester group. Early in our work, the N–H binding site was confirmed when it was found that no compound was active with the N–H proton missing. All of the active compounds were para-substituted with an electron-withdrawing group. A series of compounds with vinyl proton substitution has recently synthesized. The title compound, 3-(4-chlorophenylamino)-2,5-dimethylcyclohex-2-enone was exclusively active in the maximal electroshock seizure evaluation (MES) in mice, indicative of protection against tonic-clonic convulsions in humans. The MES test with mice revealed no activity at the 30 mg kg^-1 dose, however in the 100 mg kg^-1 dose, 3/3 of the animals were protected at 30 minutes and 0/3 of the animals were protected at 4 h. At a dose of 300 mg kg^-1, 1/1 animals were protected 30 min and 4 h. There was toxicity at 30 min in 2/4 animals. In the rat MES study, at a dose of 30 mg kg^-1, 1/4 of the animals were protected at 1 and 2 h with no toxicity.

Since the shape of the molecule is important in determining binding to the receptor sites it is of interest to note that the dihedral angle between the phenyl ring and the conjugated part of the cyclohexene ring is 61.7 (2)°. The backbone of the cyclohexene ring is disordered over two conformations with occupancies of 0.602 (7) and 0.398 (7), respectively. In addition the compound is a racemic twin (Flack parameter of 0.58 (4)). The molecules are linked in chains in the b direction by intermolecular N—H···O hydrogen bonds.

Related literature top

The title compound 3-(4-chlorophenylamino)-2,5-dimethylcyclohex-2-enone possesses significant anticonvulsant properties. For the anticonvulsant properties of enaminones, see: Edafiogho et al. (1992); Eddington et al. (2003); Scott et al. (1993, 1995). For related structures see: Alexander et al. (2010, 2011).

Experimental top

Iodomethane (11.2 ml, 0.18 mol, 1.5 equiv) was added to a solution of 5-methyl-1,3-cyclohexanedione (15.0 g, 0.119 mol) in 4 N aqueous sodium hydroxide (30 mL, 1.0 equiv of NaOH) in a two-neck 250 ml round bottom flask fitted with a magnetic stirrer and condenser. The solution was refluxed for 20 h and cooled to room temperature, then refrigerated at 0°C overnight. Vacuum filtration of the reaction mixture gave a crystalline mass dried to yield 9.24 g (54%). The crystalline mass, 2,5-dimethyl-1,3-cyclohexadione (2.10 g, 15 mmol), mp 170–172°C (lit. mp 130–131.5°C), 4-chloroaniline (2.32 g, 18 mmol), and toluene (60 ml) was added to a 150 ml single neck round bottom flask containing a stir bar. The solution was refluxed and stirred for 6 h with azeotropic removal of water by Dean-Stark trap. After standing overnight, crystals appeared. Evaporation under reduced pressure yielded crystals that were recrystallized from EtOAc, 44.3% yield (mp 183–185°C).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Diagram of 3-(4-Chlorophenylamino)-2,5-dimethylcyclohex-2-enone showing atom labeling scheme. Thermal ellipsoids drawn at the 30% probability level.
	Fig. 2. The molecular packing for 3-(4-Chlorophenylamino)-2,5-dimethylcyclohex-2-enone viewed down the a axis. Intermolecular interactions are shown by dashed lines.

3-(4-Chloroanilino)-2,5-dimethylcyclohex-2-en-1-one top

Crystal data top

C₁₄H₁₆ClNO	F(000) = 264
M_r = 249.73	D_x = 1.250 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2yb	Cell parameters from 1339 reflections
a = 6.0775 (5) Å	θ = 5.0–73.9°
b = 8.8106 (5) Å	µ = 2.41 mm⁻¹
c = 12.5794 (7) Å	T = 295 K
β = 99.904 (7)°	Chunk, colorless
V = 663.5 (1) Å³	0.45 × 0.28 × 0.10 mm
Z = 2

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	1705 independent reflections
Radiation source: Enhance (Cu) X-ray Source	1417 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 10.5081 pixels mm^-1	θ_max = 74.1°, θ_min = 6.2°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −10→5
T_min = 0.679, T_max = 1.000	l = −13→15
2292 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.150	w = 1/[σ²(F_o²) + (0.1145P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
1705 reflections	Δρ_max = 0.22 e Å⁻³
171 parameters	Δρ_min = −0.17 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 259 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.58 (4)

Crystal data top

C₁₄H₁₆ClNO	V = 663.5 (1) Å³
M_r = 249.73	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 6.0775 (5) Å	µ = 2.41 mm⁻¹
b = 8.8106 (5) Å	T = 295 K
c = 12.5794 (7) Å	0.45 × 0.28 × 0.10 mm
β = 99.904 (7)°

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	1705 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	1417 reflections with I > 2σ(I)
T_min = 0.679, T_max = 1.000	R_int = 0.029
2292 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	H-atom parameters constrained
wR(F²) = 0.150	Δρ_max = 0.22 e Å⁻³
S = 1.00	Δρ_min = −0.17 e Å⁻³
1705 reflections	Absolute structure: Flack (1983), 259 Friedel pairs
171 parameters	Absolute structure parameter: 0.58 (4)
1 restraint

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.8577 (2)	−0.13354 (18)	0.49024 (9)	0.1059 (5)
O1	0.7909 (4)	0.7372 (4)	−0.0704 (2)	0.0739 (7)
N1	0.6375 (5)	0.3591 (5)	0.1708 (2)	0.0660 (7)
H1	0.5033	0.3524	0.1357	0.079*
C1	0.7018 (5)	0.2490 (4)	0.2532 (2)	0.0577 (8)
C2	0.5554 (6)	0.2139 (6)	0.3223 (3)	0.0706 (10)
H2A	0.4243	0.2693	0.3193	0.085*
C3	0.6030 (7)	0.0966 (6)	0.3961 (3)	0.0775 (11)
H3A	0.5036	0.0717	0.4419	0.093*
C4	0.7978 (7)	0.0183 (5)	0.4006 (3)	0.0716 (10)
C5	0.9464 (6)	0.0537 (5)	0.3342 (3)	0.0685 (9)
H5A	1.0803	0.0009	0.3397	0.082*
C6	0.8969 (6)	0.1680 (5)	0.2591 (3)	0.0630 (8)
H6A	0.9957	0.1904	0.2125	0.076*
C7	0.7639 (6)	0.4728 (4)	0.1416 (3)	0.0576 (8)
C8	0.7074 (6)	0.5456 (4)	0.0452 (3)	0.0576 (7)
C9	0.8352 (5)	0.6705 (5)	0.0176 (3)	0.0614 (8)
C10A	1.051 (3)	0.719 (3)	0.0899 (17)	0.066 (3)	0.602 (7)
H10A	1.0710	0.8274	0.0847	0.080*	0.602 (7)
H10B	1.1773	0.6689	0.0664	0.080*	0.602 (7)
C11A	1.0433 (10)	0.6749 (8)	0.2071 (5)	0.0654 (13)	0.602 (7)
H11A	0.9295	0.7376	0.2324	0.078*	0.602 (7)
C12A	0.977 (3)	0.5058 (16)	0.2158 (13)	0.059 (2)	0.602 (7)
H12A	1.0945	0.4414	0.1976	0.070*	0.602 (7)
H12B	0.9599	0.4834	0.2894	0.070*	0.602 (7)
C14A	1.270 (3)	0.708 (2)	0.279 (2)	0.081 (4)	0.602 (7)
H14A	1.3132	0.8111	0.2684	0.122*	0.602 (7)
H14B	1.3813	0.6404	0.2606	0.122*	0.602 (7)
H14C	1.2575	0.6937	0.3535	0.122*	0.602 (7)
C10B	1.015 (6)	0.732 (5)	0.110 (3)	0.066 (3)	0.398 (7)
H10C	1.1249	0.7883	0.0783	0.080*	0.398 (7)
H10D	0.9443	0.8023	0.1529	0.080*	0.398 (7)
C11B	1.1314 (16)	0.6105 (13)	0.1820 (8)	0.0654 (13)	0.398 (7)
H11B	1.1935	0.5344	0.1386	0.078*	0.398 (7)
C12B	0.950 (5)	0.540 (3)	0.233 (2)	0.059 (2)	0.398 (7)
H12C	0.8849	0.6157	0.2745	0.070*	0.398 (7)
H12D	1.0119	0.4596	0.2822	0.070*	0.398 (7)
C14B	1.321 (6)	0.673 (4)	0.272 (4)	0.081 (4)	0.398 (7)
H14D	1.4200	0.5920	0.3000	0.122*	0.398 (7)
H14E	1.2559	0.7160	0.3298	0.122*	0.398 (7)
H14F	1.4044	0.7502	0.2423	0.122*	0.398 (7)
C13	0.5116 (7)	0.4931 (5)	−0.0383 (3)	0.0716 (10)
H13A	0.5080	0.3842	−0.0402	0.107*
H13B	0.5279	0.5312	−0.1080	0.107*
H13C	0.3749	0.5306	−0.0196	0.107*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1398 (11)	0.0944 (8)	0.0775 (6)	0.0012 (8)	0.0015 (6)	0.0320 (6)
O1	0.0719 (15)	0.0806 (17)	0.0706 (14)	0.0063 (14)	0.0158 (11)	0.0202 (13)
N1	0.0611 (14)	0.0737 (18)	0.0575 (14)	−0.0048 (16)	−0.0060 (11)	0.0102 (15)
C1	0.0651 (18)	0.0592 (19)	0.0451 (14)	−0.0076 (16)	−0.0009 (12)	0.0016 (13)
C2	0.0615 (18)	0.085 (3)	0.0630 (18)	−0.0002 (19)	0.0042 (14)	0.0081 (18)
C3	0.074 (2)	0.100 (3)	0.0582 (17)	−0.009 (2)	0.0091 (15)	0.015 (2)
C4	0.087 (3)	0.068 (2)	0.0535 (17)	−0.008 (2)	−0.0037 (15)	0.0098 (16)
C5	0.074 (2)	0.065 (2)	0.0623 (18)	0.003 (2)	−0.0017 (15)	−0.0009 (17)
C6	0.0663 (18)	0.066 (2)	0.0556 (15)	−0.0063 (19)	0.0059 (13)	−0.0038 (16)
C7	0.0562 (16)	0.0566 (19)	0.0579 (16)	−0.0011 (15)	0.0042 (12)	−0.0010 (15)
C8	0.0563 (16)	0.0581 (18)	0.0566 (16)	0.0059 (16)	0.0046 (12)	−0.0017 (15)
C9	0.0585 (16)	0.0611 (19)	0.0660 (18)	0.0088 (17)	0.0144 (14)	0.0059 (17)
C10A	0.057 (7)	0.072 (6)	0.073 (8)	−0.005 (5)	0.021 (4)	0.005 (6)
C11A	0.062 (3)	0.060 (4)	0.070 (3)	0.000 (3)	0.001 (2)	−0.007 (3)
C12A	0.065 (5)	0.051 (7)	0.056 (6)	0.003 (5)	0.000 (3)	−0.006 (4)
C14A	0.070 (10)	0.075 (10)	0.092 (4)	−0.006 (6)	−0.007 (6)	−0.005 (7)
C10B	0.057 (7)	0.072 (6)	0.073 (8)	−0.005 (5)	0.021 (4)	0.005 (6)
C11B	0.062 (3)	0.060 (4)	0.070 (3)	0.000 (3)	0.001 (2)	−0.007 (3)
C12B	0.065 (5)	0.051 (7)	0.056 (6)	0.003 (5)	0.000 (3)	−0.006 (4)
C14B	0.070 (10)	0.075 (10)	0.092 (4)	−0.006 (6)	−0.007 (6)	−0.005 (7)
C13	0.072 (2)	0.075 (2)	0.0617 (19)	0.000 (2)	−0.0045 (16)	0.0077 (18)

Geometric parameters (Å, º) top

Cl1—C4	1.747 (4)	C10A—H10B	0.9700
O1—C9	1.241 (4)	C11A—C14A	1.54 (2)
N1—C7	1.351 (5)	C11A—C12A	1.552 (18)
N1—C1	1.424 (5)	C11A—H11A	0.9800
N1—H1	0.8600	C12A—H12A	0.9700
C1—C6	1.375 (5)	C12A—H12B	0.9700
C1—C2	1.382 (5)	C14A—H14A	0.9600
C2—C3	1.386 (6)	C14A—H14B	0.9600
C2—H2A	0.9300	C14A—H14C	0.9600
C3—C4	1.363 (6)	C10B—C11B	1.50 (4)
C3—H3A	0.9300	C10B—H10C	0.9700
C4—C5	1.367 (5)	C10B—H10D	0.9700
C5—C6	1.378 (6)	C11B—C12B	1.50 (3)
C5—H5A	0.9300	C11B—C14B	1.58 (5)
C6—H6A	0.9300	C11B—H11B	0.9800
C7—C8	1.363 (5)	C12B—H12C	0.9700
C7—C12A	1.489 (19)	C12B—H12D	0.9700
C7—C12B	1.58 (3)	C14B—H14D	0.9600
C8—C9	1.424 (5)	C14B—H14E	0.9600
C8—C13	1.518 (5)	C14B—H14F	0.9600
C9—C10A	1.52 (3)	C13—H13A	0.9600
C9—C10B	1.55 (4)	C13—H13B	0.9600
C10A—C11A	1.53 (2)	C13—H13C	0.9600
C10A—H10A	0.9700

C7—N1—C1	127.3 (3)	C10A—C11A—C14A	110.2 (14)
C7—N1—H1	116.4	C10A—C11A—C12A	111.1 (13)
C1—N1—H1	116.4	C14A—C11A—C12A	110.9 (12)
C6—C1—C2	119.5 (3)	C10A—C11A—H11A	108.2
C6—C1—N1	121.3 (3)	C14A—C11A—H11A	108.2
C2—C1—N1	119.0 (3)	C12A—C11A—H11A	108.2
C1—C2—C3	120.4 (4)	C7—C12A—C11A	110.6 (11)
C1—C2—H2A	119.8	C7—C12A—H12A	109.5
C3—C2—H2A	119.8	C11A—C12A—H12A	109.5
C4—C3—C2	119.0 (4)	C7—C12A—H12B	109.5
C4—C3—H3A	120.5	C11A—C12A—H12B	109.5
C2—C3—H3A	120.5	H12A—C12A—H12B	108.1
C3—C4—C5	121.3 (4)	C11B—C10B—C9	114 (3)
C3—C4—Cl1	119.8 (3)	C11B—C10B—H10C	108.8
C5—C4—Cl1	118.9 (3)	C9—C10B—H10C	108.8
C4—C5—C6	119.8 (4)	C11B—C10B—H10D	108.8
C4—C5—H5A	120.1	C9—C10B—H10D	108.8
C6—C5—H5A	120.1	H10C—C10B—H10D	107.7
C1—C6—C5	120.1 (3)	C10B—C11B—C12B	104.5 (18)
C1—C6—H6A	120.0	C10B—C11B—C14B	113 (2)
C5—C6—H6A	120.0	C12B—C11B—C14B	110 (2)
N1—C7—C8	121.5 (3)	C10B—C11B—H11B	109.7
N1—C7—C12A	116.6 (8)	C12B—C11B—H11B	109.7
C8—C7—C12A	121.7 (8)	C14B—C11B—H11B	109.7
N1—C7—C12B	116.5 (12)	C11B—C12B—C7	109.0 (17)
C8—C7—C12B	120.8 (12)	C11B—C12B—H12C	109.9
C12A—C7—C12B	15.4 (10)	C7—C12B—H12C	109.9
C7—C8—C9	121.1 (3)	C11B—C12B—H12D	109.9
C7—C8—C13	121.3 (3)	C7—C12B—H12D	109.9
C9—C8—C13	117.6 (3)	H12C—C12B—H12D	108.3
O1—C9—C8	122.6 (3)	C11B—C14B—H14D	109.5
O1—C9—C10A	115.7 (10)	C11B—C14B—H14E	109.5
C8—C9—C10A	121.3 (10)	H14D—C14B—H14E	109.5
O1—C9—C10B	121.3 (16)	C11B—C14B—H14F	109.5
C8—C9—C10B	115.6 (15)	H14D—C14B—H14F	109.5
C10A—C9—C10B	14.3 (11)	H14E—C14B—H14F	109.5
C9—C10A—C11A	109.7 (13)	C8—C13—H13A	109.5
C9—C10A—H10A	109.7	C8—C13—H13B	109.5
C11A—C10A—H10A	109.7	H13A—C13—H13B	109.5
C9—C10A—H10B	109.7	C8—C13—H13C	109.5
C11A—C10A—H10B	109.7	H13A—C13—H13C	109.5
H10A—C10A—H10B	108.2	H13B—C13—H13C	109.5

C7—N1—C1—C6	−49.7 (6)	C13—C8—C9—C10A	−172.1 (8)
C7—N1—C1—C2	136.0 (4)	C7—C8—C9—C10B	−9.3 (13)
C6—C1—C2—C3	−1.0 (6)	C13—C8—C9—C10B	173.0 (13)
N1—C1—C2—C3	173.4 (4)	O1—C9—C10A—C11A	159.1 (10)
C1—C2—C3—C4	1.1 (6)	C8—C9—C10A—C11A	−27.6 (17)
C2—C3—C4—C5	0.3 (6)	C10B—C9—C10A—C11A	43 (10)
C2—C3—C4—Cl1	−178.1 (3)	C9—C10A—C11A—C14A	174.3 (12)
C3—C4—C5—C6	−1.7 (6)	C9—C10A—C11A—C12A	50.9 (17)
Cl1—C4—C5—C6	176.7 (3)	N1—C7—C12A—C11A	−152.2 (7)
C2—C1—C6—C5	−0.5 (5)	C8—C7—C12A—C11A	32.7 (10)
N1—C1—C6—C5	−174.8 (3)	C12B—C7—C12A—C11A	−59 (6)
C4—C5—C6—C1	1.9 (6)	C10A—C11A—C12A—C7	−54.1 (13)
C1—N1—C7—C8	162.5 (3)	C14A—C11A—C12A—C7	−177.0 (10)
C1—N1—C7—C12A	−12.5 (7)	O1—C9—C10B—C11B	−149.8 (12)
C1—N1—C7—C12B	−29.8 (10)	C8—C9—C10B—C11B	37.9 (17)
N1—C7—C8—C9	176.7 (3)	C10A—C9—C10B—C11B	−79 (10)
C12A—C7—C8—C9	−8.4 (7)	C9—C10B—C11B—C12B	−63.3 (18)
C12B—C7—C8—C9	9.6 (10)	C9—C10B—C11B—C14B	177.3 (18)
N1—C7—C8—C13	−5.6 (6)	C10B—C11B—C12B—C7	60 (2)
C12A—C7—C8—C13	169.2 (5)	C14B—C11B—C12B—C7	−178.3 (16)
C12B—C7—C8—C13	−172.8 (9)	N1—C7—C12B—C11B	155.6 (11)
C7—C8—C9—O1	178.5 (4)	C8—C7—C12B—C11B	−36.6 (17)
C13—C8—C9—O1	0.7 (5)	C12A—C7—C12B—C11B	61 (6)
C7—C8—C9—C10A	5.6 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.10	2.897 (4)	155
C6—H6A···O1ⁱⁱ	0.93	2.42	3.340 (4)	172
C12A—H12A···O1ⁱⁱ	0.97	2.58	3.439 (9)	147
C12B—H12D···Cl1ⁱⁱⁱ	0.97	2.95	3.79 (3)	146

Symmetry codes: (i) −x+1, y−1/2, −z; (ii) −x+2, y−1/2, −z; (iii) −x+2, y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₆ClNO
M_r	249.73
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	295
a, b, c (Å)	6.0775 (5), 8.8106 (5), 12.5794 (7)
β (°)	99.904 (7)
V (Å³)	663.5 (1)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	2.41
Crystal size (mm)	0.45 × 0.28 × 0.10

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.679, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	2292, 1705, 1417
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.150, 1.00
No. of reflections	1705
No. of parameters	171
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.17
Absolute structure	Flack (1983), 259 Friedel pairs
Absolute structure parameter	0.58 (4)

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	2.10	2.897 (4)	155
C6—H6A···O1ⁱⁱ	0.93	2.42	3.340 (4)	172
C12A—H12A···O1ⁱⁱ	0.97	2.58	3.439 (9)	147
C12B—H12D···Cl1ⁱⁱⁱ	0.97	2.95	3.79 (3)	146

Symmetry codes: (i) −x+1, y−1/2, −z; (ii) −x+2, y−1/2, −z; (iii) −x+2, y+1/2, −z+1.

Acknowledgements

The authors are indebted to Mr James P. Stables, Epilepsy Branch, Division of Convulsive, Developmental and Neuromuscular Disorders, National Institute of Neurological Disorders and Stroke, for helpful discussions and initial data. The authors wish to acknowledge E. Jeannette Andrews, EdD, Deputy Director of the Center of Excellence at Howard University College of Pharmacy, Nursing and Allied Health Sciences, for her generous assistance in completing this project. RJB wishes to acknowledge the NSF–MRI program (grant CHE-0619278) for funds to purchase the diffractometer.

References

Alexander, M. S., North, H., Scott, K. R. & Butcher, R. J. (2010). Acta Cryst. E66, o3229. Web of Science CSD CrossRef IUCr Journals Google Scholar
Alexander, M. S., North, H., Scott, K. R. & Butcher, R. J. (2011). Acta Cryst. E67, o224. Web of Science CSD CrossRef IUCr Journals Google Scholar
Edafiogho, I. O., Hinko, C. N., Chang, H., Moore, J. A., Mulzac, D., Nicholson, J. M. & Scott, K. R. (1992). J. Med. Chem. 35, 2798–2805. CrossRef PubMed CAS Web of Science Google Scholar
Eddington, N. D., Cox, D. S., Khurana, M., Salama, N. N., Stables, J. P., Harrison, S. J., Negussie, A., Taylor, R. S., Tran, U. Q., Moore, J. A., Barrow, J. C. & Scott, K. R. (2003). Eur. J. Med. Chem. 38, 49–64. Web of Science CrossRef PubMed CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England. Google Scholar
Scott, K. R., Edafiogho, I. O., Richardson, E. R., Farrar, V. A., Moore, J. A., Tietz, E., Hinko, C. N., Chang, H., El-Assadi, A. & Nicholson, J. M. (1993). J. Med. Chem. 36, 1947–1955. CrossRef CAS PubMed Web of Science Google Scholar
Scott, K. R., Rankin, G. O., Stables, J. P., Alexander, M. S., Edafiogho, I. O., Farrar, V. A., Kolen, K. R., Moore, J. A., Sims, L. D. & Tonnu, A. D. (1995). J. Med. Chem. 38, 4033–4043. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 5| May 2011| Pages o1283-o1284

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