2-Chloro-3-(4-chloro­benzamido)-1,4-naphthoquinone

Brandy, Y.; Butcher, R.J.; Adesiyun, T.A.; Berhe, S.; Bakare, O.

doi:10.1107/S1600536808040993

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o64

doi:10.1107/S1600536808040993

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2-Chloro-3-(4-chlorobenzamido)-1,4-naphthoquinone

Yakini Brandy,^a Ray J. Butcher,^a ^* Tolulope A. Adesiyun,^a Solomon Berhe ^a and Oladapo Bakare ^a

^aDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
^*Correspondence e-mail: rbutcher99@yahoo.com

(Received 3 December 2008; accepted 4 December 2008; online 10 December 2008)

The naphthoquinone ring is almost perpendicular [dihedral angle 71.02 (3)°] to the phenyl group of the title compound, C₁₇H₉Cl₂NO₃, while the dihedral angle between the amide group and the 4-chlorophenyl ring is 21.9 (2)°. The conformation of the N—H and C=O bonds are anti to each other. N—H⋯Cl hydrogen bonds link the molecules into chains in the a-axis direction. In addition, these chains are linked by weak intermolecular C—H⋯O interactions.

Related literature

For similar structures see: Lien et al. (1997 ); Huang et al. (2005 ); Bakare et al. (2003 ); Copeland et al. (2007 ); Win et al. (2005 ); Rubin-Preminger et al. (2004 ). For related literature, see: Gowda, Kožíšek et al. (2008 ); Gowda, Tokarčík et al. (2008 ); van Oosten et al. (2008 ); Shen et al. (2008 ).

Experimental

Crystal data

C₁₇H₉Cl₂NO₃
M_r = 346.15
Monoclinic, P 2₁ /c
a = 5.6011 (2) Å
b = 8.7237 (3) Å
c = 29.7957 (9) Å
β = 93.504 (3)°
V = 1453.16 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 200 (2) K
0.49 × 0.41 × 0.12 mm

Data collection

Oxford Diffraction Gemini R diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED (including SCALE3 ABSPACK). Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.887, T_max = 1.000 (expected range = 0.839–0.946)
13882 measured reflections
4842 independent reflections
2832 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.086
S = 0.93
4842 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H0A⋯Cl1ⁱ	0.88	2.89	3.6491 (12)	145
C14—H14A⋯O2ⁱⁱ	0.95	2.40	3.2517 (19)	149
Symmetry codes: (i) x-1, y, z; (ii) $[-x-1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED (including SCALE3 ABSPACK). Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED (including SCALE3 ABSPACK). Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; 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 global, I. DOI: 10.1107/S1600536808040993/at2690sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808040993/at2690Isup2.hkl

checkCIF report

Comment top

The amido and imido derivatives of 3-chloro-1,4-naphthoquinone are well known for their anti-inflammatory, antiplatelet, antiallergic and anticancer activities (Lien et al., 1997; Huang et al., 2005; Bakare et al., 2003; Copeland et al., 2007). The title compound, 2-chloro-3-(p-chlorobenzamido)-1,4-naphthoquinone was obtained as an intermediate in the synthesis of some oxazolo-1,4-naphthoquinone and imido-substituted-1,4-naphthoquinone analogs.

The naphthoquinone ring is almost perpendicular to the phenyl group of the title compound C₁₇H₉Cl₂NO₃, while the dihedral angle betwen the amide group and the 4-chlorophenyl ring is 21.9 (2)° (Fig. 1). The conformation of the N—H and C=O bonds are anti to each other (Gowda, Kožíšek et al., 2008; Gowda, Tokarčík et al., 2008). N—H···Cl hydrogen bonds link the molecules into chains in the a direction. In addition, these chains are linked by weak intermolecular Ar—H···O interactions (Fig. 2, Table 1).

Related literature top

For similar structures see: Lien et al. (1997); Huang et al. (2005); Bakare et al. (2003); Copeland et al. (2007); Win et al. (2005); Rubin-Preminger et al. (2004). For related literature, see: Gowda, Kožíšek et al. (2008); Gowda, Tokarčík et al. (2008); van Oosten et al. (2008); Shen et al. (2008).

Experimental top

A mixture of 2-amino-3-chloro-1,4-naphthoquinone (213 mg, 1.03 mmol) and 4-chloro-benzoylchloride (2 ml) was refluxed for 2 1/2 h (powerstat setting at 70). The reaction mixture was cooled to room temperature. The precipitate was isolated by vacuum filtration and the yellow-grey solid was washed with diethyl ether. The crude was recrystallized from ethanol (20 ml) to obtain a yellow solid (67 mg, 18.8%). Crystals for x-ray study were obtained by recrystallization from methanol.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); 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. View of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 20% probability level.
	Fig. 2. View of the packing viewed down the a axis. Dashed bonds show weak C—H···O interactions.

2-Chloro-3-(4-chlorobenzamido)-1,4-naphthoquinone top

Crystal data top

C₁₇H₉Cl₂NO₃	F(000) = 704
M_r = 346.15	D_x = 1.582 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4629 reflections
a = 5.6011 (2) Å	θ = 4.6–32.5°
b = 8.7237 (3) Å	µ = 0.46 mm⁻¹
c = 29.7957 (9) Å	T = 200 K
β = 93.504 (3)°	Plate, pale yellow
V = 1453.16 (8) Å³	0.49 × 0.41 × 0.12 mm
Z = 4

Data collection top

Oxford Diffraction Gemini R diffractometer	4842 independent reflections
Radiation source: fine-focus sealed tube	2832 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 10.5081 pixels mm^-1	θ_max = 32.6°, θ_min = 4.6°
ϕ and ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −12→12
T_min = 0.887, T_max = 1.000	l = −44→44
13882 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H-atom parameters constrained
S = 0.93	w = 1/[σ²(F_o²) + (0.0416P)²] where P = (F_o² + 2F_c²)/3
4842 reflections	(Δ/σ)_max = 0.001
208 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₇H₉Cl₂NO₃	V = 1453.16 (8) Å³
M_r = 346.15	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.6011 (2) Å	µ = 0.46 mm⁻¹
b = 8.7237 (3) Å	T = 200 K
c = 29.7957 (9) Å	0.49 × 0.41 × 0.12 mm
β = 93.504 (3)°

Data collection top

Oxford Diffraction Gemini R diffractometer	4842 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	2832 reflections with I > 2σ(I)
T_min = 0.887, T_max = 1.000	R_int = 0.035
13882 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 0.93	Δρ_max = 0.29 e Å⁻³
4842 reflections	Δρ_min = −0.36 e Å⁻³
208 parameters

Special details top

Experimental. (CrysAlis RED; Oxford Diffraction, 2007) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Cl1	0.42210 (6)	0.13331 (4)	0.298854 (11)	0.02796 (10)
Cl2	−0.42944 (7)	−0.05032 (6)	0.057164 (13)	0.04852 (14)
O1	0.54644 (18)	0.07511 (14)	0.39281 (4)	0.0401 (3)
O2	−0.26101 (17)	−0.20745 (14)	0.33569 (3)	0.0378 (3)
O3	0.31583 (17)	−0.12832 (14)	0.24103 (3)	0.0364 (3)
N	−0.02512 (19)	−0.06128 (15)	0.27365 (4)	0.0273 (3)
H0A	−0.1786	−0.0415	0.2689	0.033*
C1	0.3653 (2)	0.00688 (18)	0.38026 (5)	0.0275 (3)
C2	0.2705 (2)	0.01309 (17)	0.33244 (4)	0.0251 (3)
C3	0.0712 (2)	−0.06238 (17)	0.31773 (4)	0.0240 (3)
C4	−0.0749 (2)	−0.14777 (18)	0.34975 (5)	0.0264 (3)
C5	0.0144 (2)	−0.15604 (18)	0.39758 (5)	0.0272 (3)
C6	−0.1138 (3)	−0.2369 (2)	0.42817 (5)	0.0391 (4)
H6A	−0.2591	−0.2864	0.4186	0.047*
C7	−0.0289 (3)	−0.2451 (3)	0.47288 (5)	0.0477 (5)
H7A	−0.1169	−0.3002	0.4939	0.057*
C8	0.1823 (3)	−0.1737 (2)	0.48705 (5)	0.0477 (5)
H8A	0.2390	−0.1794	0.5177	0.057*
C9	0.3111 (3)	−0.0940 (2)	0.45660 (5)	0.0391 (4)
H9A	0.4574	−0.0459	0.4663	0.047*
C10	0.2273 (2)	−0.08383 (18)	0.41170 (5)	0.0287 (3)
C11	0.1070 (3)	−0.08964 (17)	0.23680 (5)	0.0263 (3)
C12	−0.0252 (2)	−0.07098 (17)	0.19218 (4)	0.0245 (3)
C13	−0.2316 (2)	0.01736 (18)	0.18635 (5)	0.0277 (3)
H13A	−0.2882	0.0726	0.2110	0.033*
C14	−0.3550 (3)	0.02492 (19)	0.14462 (5)	0.0315 (3)
H14A	−0.4966	0.0846	0.1406	0.038*
C15	−0.2697 (3)	−0.05531 (19)	0.10907 (5)	0.0307 (3)
C16	−0.0608 (3)	−0.1395 (2)	0.11357 (5)	0.0319 (3)
H16A	−0.0020	−0.1913	0.0885	0.038*
C17	0.0618 (3)	−0.14706 (19)	0.15551 (5)	0.0295 (3)
H17A	0.2058	−0.2045	0.1592	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.02827 (17)	0.0286 (2)	0.02758 (17)	−0.00541 (15)	0.00608 (13)	0.00212 (15)
Cl2	0.0514 (2)	0.0680 (4)	0.02503 (18)	0.0176 (2)	−0.00744 (17)	−0.0029 (2)
O1	0.0364 (6)	0.0500 (8)	0.0334 (6)	−0.0141 (6)	−0.0034 (5)	−0.0042 (5)
O2	0.0321 (5)	0.0490 (8)	0.0318 (6)	−0.0152 (5)	−0.0010 (5)	0.0023 (5)
O3	0.0328 (6)	0.0476 (8)	0.0288 (5)	0.0120 (5)	0.0007 (4)	−0.0072 (5)
N	0.0240 (6)	0.0383 (8)	0.0196 (5)	0.0012 (5)	0.0019 (5)	0.0013 (5)
C1	0.0266 (7)	0.0307 (9)	0.0253 (7)	−0.0004 (6)	0.0021 (6)	−0.0031 (6)
C2	0.0272 (7)	0.0247 (8)	0.0239 (7)	0.0006 (6)	0.0058 (6)	−0.0012 (6)
C3	0.0252 (6)	0.0278 (8)	0.0192 (6)	0.0026 (6)	0.0028 (5)	−0.0013 (6)
C4	0.0278 (7)	0.0268 (8)	0.0248 (7)	−0.0014 (6)	0.0030 (6)	−0.0008 (6)
C5	0.0294 (7)	0.0302 (9)	0.0220 (6)	0.0000 (6)	0.0023 (6)	0.0005 (6)
C6	0.0374 (8)	0.0517 (12)	0.0286 (7)	−0.0087 (8)	0.0041 (7)	0.0049 (8)
C7	0.0502 (10)	0.0654 (14)	0.0282 (8)	−0.0078 (9)	0.0083 (7)	0.0117 (9)
C8	0.0532 (10)	0.0680 (15)	0.0214 (7)	0.0003 (10)	−0.0008 (7)	0.0049 (8)
C9	0.0374 (8)	0.0562 (12)	0.0232 (7)	−0.0047 (8)	−0.0026 (6)	−0.0018 (7)
C10	0.0296 (7)	0.0348 (9)	0.0218 (6)	0.0004 (6)	0.0023 (6)	−0.0028 (6)
C11	0.0306 (7)	0.0258 (8)	0.0228 (7)	0.0018 (6)	0.0033 (6)	−0.0012 (6)
C12	0.0275 (7)	0.0260 (8)	0.0201 (6)	−0.0020 (6)	0.0034 (5)	0.0002 (6)
C13	0.0321 (7)	0.0282 (8)	0.0233 (7)	0.0034 (6)	0.0060 (6)	−0.0017 (6)
C14	0.0293 (7)	0.0361 (9)	0.0291 (7)	0.0071 (7)	0.0022 (6)	0.0014 (7)
C15	0.0359 (8)	0.0359 (9)	0.0202 (6)	0.0015 (7)	−0.0008 (6)	0.0018 (7)
C16	0.0347 (8)	0.0400 (10)	0.0215 (7)	0.0064 (7)	0.0051 (6)	−0.0032 (7)
C17	0.0292 (7)	0.0348 (9)	0.0246 (7)	0.0052 (6)	0.0035 (6)	−0.0009 (6)

Geometric parameters (Å, º) top

Cl1—C2	1.7105 (15)	C7—C8	1.380 (2)
Cl2—C15	1.7394 (14)	C7—H7A	0.9500
O1—C1	1.2154 (17)	C8—C9	1.381 (2)
O2—C4	1.2166 (16)	C8—H8A	0.9500
O3—C11	1.2167 (16)	C9—C10	1.3932 (19)
N—C11	1.3834 (18)	C9—H9A	0.9500
N—C3	1.3890 (15)	C11—C12	1.4905 (19)
N—H0A	0.8800	C12—C17	1.392 (2)
C1—C10	1.480 (2)	C12—C13	1.392 (2)
C1—C2	1.4907 (18)	C13—C14	1.3867 (19)
C2—C3	1.3461 (19)	C13—H13A	0.9500
C3—C4	1.494 (2)	C14—C15	1.379 (2)
C4—C5	1.4829 (19)	C14—H14A	0.9500
C5—C6	1.387 (2)	C15—C16	1.381 (2)
C5—C10	1.391 (2)	C16—C17	1.3903 (19)
C6—C7	1.389 (2)	C16—H16A	0.9500
C6—H6A	0.9500	C17—H17A	0.9500

C11—N—C3	123.62 (11)	C8—C9—C10	120.27 (15)
C11—N—H0A	118.2	C8—C9—H9A	119.9
C3—N—H0A	118.2	C10—C9—H9A	119.9
O1—C1—C10	121.71 (13)	C5—C10—C9	119.60 (14)
O1—C1—C2	121.20 (14)	C5—C10—C1	121.47 (12)
C10—C1—C2	117.08 (12)	C9—C10—C1	118.91 (13)
C3—C2—C1	122.21 (13)	O3—C11—N	121.65 (12)
C3—C2—Cl1	122.74 (11)	O3—C11—C12	123.01 (13)
C1—C2—Cl1	114.90 (10)	N—C11—C12	115.34 (12)
C2—C3—N	124.82 (13)	C17—C12—C13	119.63 (12)
C2—C3—C4	120.79 (12)	C17—C12—C11	118.00 (12)
N—C3—C4	114.27 (12)	C13—C12—C11	122.36 (12)
O2—C4—C5	122.80 (13)	C14—C13—C12	120.19 (13)
O2—C4—C3	119.01 (12)	C14—C13—H13A	119.9
C5—C4—C3	118.19 (12)	C12—C13—H13A	119.9
C6—C5—C10	120.03 (13)	C15—C14—C13	119.16 (13)
C6—C5—C4	119.89 (13)	C15—C14—H14A	120.4
C10—C5—C4	120.08 (13)	C13—C14—H14A	120.4
C5—C6—C7	119.71 (15)	C14—C15—C16	121.78 (13)
C5—C6—H6A	120.1	C14—C15—Cl2	119.11 (11)
C7—C6—H6A	120.1	C16—C15—Cl2	119.11 (11)
C8—C7—C6	120.49 (16)	C15—C16—C17	118.79 (14)
C8—C7—H7A	119.8	C15—C16—H16A	120.6
C6—C7—H7A	119.8	C17—C16—H16A	120.6
C7—C8—C9	119.89 (14)	C16—C17—C12	120.37 (13)
C7—C8—H8A	120.1	C16—C17—H17A	119.8
C9—C8—H8A	120.1	C12—C17—H17A	119.8

O1—C1—C2—C3	179.54 (14)	C6—C5—C10—C1	−178.31 (15)
C10—C1—C2—C3	−1.3 (2)	C4—C5—C10—C1	2.1 (2)
O1—C1—C2—Cl1	−4.8 (2)	C8—C9—C10—C5	−0.8 (3)
C10—C1—C2—Cl1	174.35 (11)	C8—C9—C10—C1	177.93 (16)
C1—C2—C3—N	−179.82 (14)	O1—C1—C10—C5	177.09 (15)
Cl1—C2—C3—N	4.8 (2)	C2—C1—C10—C5	−2.0 (2)
C1—C2—C3—C4	4.4 (2)	O1—C1—C10—C9	−1.6 (2)
Cl1—C2—C3—C4	−170.99 (11)	C2—C1—C10—C9	179.29 (14)
C11—N—C3—C2	49.6 (2)	C3—N—C11—O3	5.2 (2)
C11—N—C3—C4	−134.37 (14)	C3—N—C11—C12	−175.37 (13)
C2—C3—C4—O2	175.91 (14)	O3—C11—C12—C17	21.9 (2)
N—C3—C4—O2	−0.3 (2)	N—C11—C12—C17	−157.54 (14)
C2—C3—C4—C5	−4.1 (2)	O3—C11—C12—C13	−159.00 (15)
N—C3—C4—C5	179.64 (12)	N—C11—C12—C13	21.6 (2)
O2—C4—C5—C6	1.2 (2)	C17—C12—C13—C14	2.4 (2)
C3—C4—C5—C6	−178.73 (15)	C11—C12—C13—C14	−176.72 (14)
O2—C4—C5—C10	−179.23 (15)	C12—C13—C14—C15	−0.4 (2)
C3—C4—C5—C10	0.8 (2)	C13—C14—C15—C16	−1.9 (2)
C10—C5—C6—C7	0.1 (3)	C13—C14—C15—Cl2	178.10 (12)
C4—C5—C6—C7	179.64 (16)	C14—C15—C16—C17	2.1 (2)
C5—C6—C7—C8	−0.2 (3)	Cl2—C15—C16—C17	−177.92 (13)
C6—C7—C8—C9	−0.3 (3)	C15—C16—C17—C12	0.0 (2)
C7—C8—C9—C10	0.7 (3)	C13—C12—C17—C16	−2.2 (2)
C6—C5—C10—C9	0.4 (2)	C11—C12—C17—C16	176.94 (14)
C4—C5—C10—C9	−179.17 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···Cl1ⁱ	0.88	2.89	3.6491 (12)	145
C14—H14A···O2ⁱⁱ	0.95	2.40	3.2517 (19)	149

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

Experimental details

Crystal data
Chemical formula	C₁₇H₉Cl₂NO₃
M_r	346.15
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	5.6011 (2), 8.7237 (3), 29.7957 (9)
β (°)	93.504 (3)
V (Å³)	1453.16 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.46
Crystal size (mm)	0.49 × 0.41 × 0.12

Data collection
Diffractometer	Oxford Diffraction Gemini R diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.887, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	13882, 4842, 2832
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.757

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.086, 0.93
No. of reflections	4842
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.36

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), 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
N—H0A···Cl1ⁱ	0.88	2.89	3.6491 (12)	145.1
C14—H14A···O2ⁱⁱ	0.95	2.40	3.2517 (19)	149.3

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

Acknowledgements

RJB acknowledges the Laboratory for the Structure of Matter at the Naval Research Laboratory for access to their diffractometers.

References

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