2-Chloro-3-(4-chloro-benzamido)-1,4-naphthoquinone.

The naphthoquinone ring is almost perpendicular [dihedral angle 71.02 (3)°] to the phenyl group of the title compound, C(17)H(9)Cl(2)NO(3), while the dihedral angle between the amide group and the 4-chloro-phenyl 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 mol-ecules into chains in the a-axis direction. In addition, these chains are linked by weak inter-molecular C-H⋯O inter-actions.

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 = 346.15

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.086

S = 0.93

4842 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.36 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808040993/at2690sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H9Cl2NO3	F(000) = 704
Mr = 346.15	Dx = 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

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

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(Fo2) + (0.0416P)2] where P = (Fo2 + 2Fc2)/3
4842 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .