N-(3-Chloro-1,4-dioxo-1,4-di-hydro-naph-thalen-2-yl)-N-propionylpropionamide.

In the title mol-ecule, C16H14ClNO4, the four essentially planar atoms of the imide group [r.m.s. deviation = 0.0286 (11) Å] form a dihedral angle of 77.36 (13)° with the naphtho-quinone group [maximun deviation = 0.111 (2) Å for the carbonyl O atom in the naphthalene 1-position] and the two imide carbonyl groups are oriented anti with respect to each other. In the crystal, mol-ecules are connected by weak C-H⋯O hydrogen bonds, as well as π-π stacking inter-actions [centroid-centroid distance = 3.888 (3) Å], forming a three-dimensional network.

Related literature

For the synthesis and biological evaluation of imido-substituted 1,4-naphtho­quinone derivatives, see: Bakare et al. (2003 ▶); Berhe et al. (2008 ▶); Brandy et al. (2013 ▶). For the anti­cancer and anti­trypanosomal activity of related compounds, see: Bakare et al. (2003 ▶); Berhe et al. (2008 ▶); Khraiwesh et al. (2012 ▶). For a related structure, see: Butcher et al. (2013 ▶).

Experimental

Crystal data

C16H14ClNO4

M = 319.73

Triclinic,

a = 8.1362 (9) Å

b = 8.2254 (9) Å

c = 12.4471 (11) Å

α = 98.105 (8)°

β = 92.297 (8)°

γ = 116.821 (11)°

V = 730.88 (15) Å3

Z = 2

Cu Kα radiation

μ = 2.48 mm−1

T = 123 K

0.48 × 0.34 × 0.08 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.396, T max = 1.000

4648 measured reflections

2908 independent reflections

2419 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.115

S = 1.01

2908 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.30 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); 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.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813034302/lh5677sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813034302/lh5677Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813034302/lh5677Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H14ClNO4	Z = 2
Mr = 319.73	F(000) = 332
Triclinic, P1	Dx = 1.453 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 8.1362 (9) Å	Cell parameters from 1754 reflections
b = 8.2254 (9) Å	θ = 3.6–75.0°
c = 12.4471 (11) Å	µ = 2.48 mm−1
α = 98.105 (8)°	T = 123 K
β = 92.297 (8)°	Plate, colorless
γ = 116.821 (11)°	0.48 × 0.34 × 0.08 mm
V = 730.88 (15) Å3

Agilent Xcalibur (Ruby, Gemini) diffractometer	2908 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2419 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 10.5081 pixels mm-1	θmax = 75.2°, θmin = 3.6°
ω scans	h = −10→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −8→10
Tmin = 0.396, Tmax = 1.000	l = −15→15
4648 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0653P)2] where P = (Fo2 + 2Fc2)/3
2908 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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	0.34840 (7)	0.42387 (7)	0.70172 (4)	0.02795 (15)
O1	0.3577 (2)	0.2807 (2)	0.47615 (11)	0.0272 (3)
O2	0.9546 (2)	0.4037 (2)	0.73820 (12)	0.0297 (3)
O3	0.6017 (2)	0.1818 (2)	0.85542 (12)	0.0298 (3)
O4	0.7362 (2)	0.7230 (2)	0.96429 (12)	0.0313 (3)
N1	0.6911 (2)	0.4761 (2)	0.83472 (13)	0.0217 (3)
C1	0.5193 (3)	0.3762 (3)	0.65414 (16)	0.0210 (4)
C2	0.4900 (3)	0.2978 (3)	0.53419 (15)	0.0212 (4)
C3	0.6266 (3)	0.2389 (3)	0.49340 (15)	0.0208 (4)
C4	0.5978 (3)	0.1483 (3)	0.38574 (15)	0.0236 (4)
H4A	0.4934	0.1283	0.3385	0.028*
C5	0.7225 (3)	0.0869 (3)	0.34745 (16)	0.0254 (4)
H5A	0.7026	0.0243	0.2742	0.031*
C6	0.8766 (3)	0.1177 (3)	0.41683 (17)	0.0264 (4)
H6A	0.9610	0.0751	0.3907	0.032*
C7	0.9074 (3)	0.2096 (3)	0.52347 (16)	0.0253 (4)
H7A	1.0137	0.2320	0.5699	0.030*
C8	0.7822 (3)	0.2692 (3)	0.56247 (15)	0.0211 (4)
C9	0.8146 (3)	0.3624 (3)	0.67823 (15)	0.0215 (4)
C10	0.6669 (3)	0.4052 (3)	0.72075 (15)	0.0205 (4)
C11	0.6645 (3)	0.3405 (3)	0.90111 (15)	0.0227 (4)
C12	0.7214 (3)	0.4027 (3)	1.02245 (15)	0.0255 (4)
H12A	0.6392	0.4507	1.0547	0.031*
H12B	0.8498	0.5049	1.0359	0.031*
C13	0.7112 (4)	0.2455 (3)	1.07811 (17)	0.0386 (6)
H13A	0.7554	0.2926	1.1560	0.058*
H13B	0.7892	0.1949	1.0446	0.058*
H13C	0.5825	0.1479	1.0695	0.058*
C14	0.7498 (3)	0.6667 (3)	0.87202 (15)	0.0223 (4)
C15	0.8322 (3)	0.7895 (3)	0.78881 (16)	0.0268 (4)
H15A	0.7356	0.7554	0.7270	0.032*
H15B	0.9332	0.7671	0.7600	0.032*
C16	0.9083 (4)	0.9933 (3)	0.83514 (19)	0.0380 (5)
H16A	0.9591	1.0659	0.7777	0.057*
H16B	1.0067	1.0290	0.8950	0.057*
H16C	0.8086	1.0170	0.8627	0.057*

	U11	U22	U33	U12	U13	U23
Cl1	0.0231 (2)	0.0398 (3)	0.0226 (2)	0.0178 (2)	0.00071 (17)	−0.00015 (18)
O1	0.0246 (7)	0.0381 (8)	0.0195 (7)	0.0158 (7)	−0.0031 (5)	0.0034 (6)
O2	0.0244 (7)	0.0406 (9)	0.0231 (7)	0.0168 (7)	−0.0043 (6)	−0.0023 (6)
O3	0.0371 (8)	0.0241 (7)	0.0218 (7)	0.0096 (6)	−0.0017 (6)	0.0026 (6)
O4	0.0405 (9)	0.0310 (8)	0.0207 (7)	0.0158 (7)	0.0053 (6)	0.0020 (6)
N1	0.0220 (8)	0.0260 (9)	0.0156 (7)	0.0105 (7)	−0.0002 (6)	0.0018 (6)
C1	0.0184 (9)	0.0242 (9)	0.0206 (9)	0.0103 (8)	0.0026 (7)	0.0032 (7)
C2	0.0210 (9)	0.0223 (9)	0.0174 (9)	0.0072 (8)	0.0009 (7)	0.0054 (7)
C3	0.0199 (9)	0.0210 (9)	0.0182 (9)	0.0063 (7)	0.0028 (7)	0.0049 (7)
C4	0.0265 (10)	0.0235 (10)	0.0173 (9)	0.0085 (8)	0.0001 (7)	0.0045 (7)
C5	0.0317 (11)	0.0244 (10)	0.0165 (9)	0.0101 (9)	0.0040 (8)	0.0021 (7)
C6	0.0262 (10)	0.0295 (10)	0.0249 (10)	0.0134 (9)	0.0066 (8)	0.0054 (8)
C7	0.0222 (9)	0.0289 (10)	0.0229 (10)	0.0103 (8)	0.0011 (7)	0.0038 (8)
C8	0.0207 (9)	0.0223 (9)	0.0182 (9)	0.0080 (8)	0.0015 (7)	0.0037 (7)
C9	0.0198 (9)	0.0231 (9)	0.0197 (9)	0.0084 (8)	−0.0003 (7)	0.0042 (7)
C10	0.0219 (9)	0.0203 (9)	0.0168 (9)	0.0078 (8)	0.0016 (7)	0.0030 (7)
C11	0.0206 (9)	0.0267 (10)	0.0200 (9)	0.0099 (8)	0.0025 (7)	0.0053 (8)
C12	0.0280 (10)	0.0265 (10)	0.0180 (9)	0.0091 (8)	0.0009 (8)	0.0045 (7)
C13	0.0584 (15)	0.0346 (12)	0.0186 (10)	0.0182 (11)	−0.0043 (10)	0.0059 (8)
C14	0.0199 (9)	0.0270 (10)	0.0190 (9)	0.0104 (8)	−0.0003 (7)	0.0030 (7)
C15	0.0297 (10)	0.0287 (11)	0.0206 (9)	0.0122 (9)	0.0022 (8)	0.0048 (8)
C16	0.0511 (14)	0.0274 (12)	0.0303 (11)	0.0141 (11)	0.0047 (10)	0.0038 (9)

Cl1—C1	1.7117 (19)	C7—C8	1.392 (3)
O1—C2	1.214 (2)	C7—H7A	0.9500
O2—C9	1.217 (2)	C8—C9	1.486 (3)
O3—C11	1.206 (3)	C9—C10	1.492 (3)
O4—C14	1.205 (2)	C11—C12	1.507 (3)
N1—C14	1.416 (3)	C12—C13	1.523 (3)
N1—C11	1.425 (2)	C12—H12A	0.9900
N1—C10	1.425 (2)	C12—H12B	0.9900
C1—C10	1.339 (3)	C13—H13A	0.9800
C1—C2	1.504 (3)	C13—H13B	0.9800
C2—C3	1.480 (3)	C13—H13C	0.9800
C3—C4	1.394 (3)	C14—C15	1.510 (3)
C3—C8	1.404 (3)	C15—C16	1.512 (3)
C4—C5	1.394 (3)	C15—H15A	0.9900
C4—H4A	0.9500	C15—H15B	0.9900
C5—C6	1.395 (3)	C16—H16A	0.9800
C5—H5A	0.9500	C16—H16B	0.9800
C6—C7	1.384 (3)	C16—H16C	0.9800
C6—H6A	0.9500
C14—N1—C11	126.40 (16)	N1—C10—C9	116.65 (16)
C14—N1—C10	120.34 (16)	O3—C11—N1	117.25 (17)
C11—N1—C10	113.08 (16)	O3—C11—C12	123.88 (18)
C10—C1—C2	123.02 (17)	N1—C11—C12	118.84 (17)
C10—C1—Cl1	121.46 (15)	C11—C12—C13	111.82 (17)
C2—C1—Cl1	115.52 (14)	C11—C12—H12A	109.3
O1—C2—C3	122.90 (17)	C13—C12—H12A	109.3
O1—C2—C1	120.67 (17)	C11—C12—H12B	109.3
C3—C2—C1	116.41 (16)	C13—C12—H12B	109.3
C4—C3—C8	119.68 (18)	H12A—C12—H12B	107.9
C4—C3—C2	119.45 (17)	C12—C13—H13A	109.5
C8—C3—C2	120.85 (17)	C12—C13—H13B	109.5
C3—C4—C5	119.94 (18)	H13A—C13—H13B	109.5
C3—C4—H4A	120.0	C12—C13—H13C	109.5
C5—C4—H4A	120.0	H13A—C13—H13C	109.5
C4—C5—C6	119.90 (18)	H13B—C13—H13C	109.5
C4—C5—H5A	120.1	O4—C14—N1	121.10 (18)
C6—C5—H5A	120.1	O4—C14—C15	123.97 (18)
C7—C6—C5	120.52 (18)	N1—C14—C15	114.92 (16)
C7—C6—H6A	119.7	C14—C15—C16	113.04 (17)
C5—C6—H6A	119.7	C14—C15—H15A	109.0
C6—C7—C8	119.80 (18)	C16—C15—H15A	109.0
C6—C7—H7A	120.1	C14—C15—H15B	109.0
C8—C7—H7A	120.1	C16—C15—H15B	109.0
C7—C8—C3	120.15 (18)	H15A—C15—H15B	107.8
C7—C8—C9	118.99 (17)	C15—C16—H16A	109.5
C3—C8—C9	120.86 (17)	C15—C16—H16B	109.5
O2—C9—C8	122.72 (18)	H16A—C16—H16B	109.5
O2—C9—C10	119.76 (18)	C15—C16—H16C	109.5
C8—C9—C10	117.51 (16)	H16A—C16—H16C	109.5
C1—C10—N1	122.45 (17)	H16B—C16—H16C	109.5
C1—C10—C9	120.90 (17)
C10—C1—C2—O1	−177.09 (19)	Cl1—C1—C10—N1	0.3 (3)
Cl1—C1—C2—O1	3.8 (3)	C2—C1—C10—C9	0.8 (3)
C10—C1—C2—C3	4.7 (3)	Cl1—C1—C10—C9	179.78 (14)
Cl1—C1—C2—C3	−174.35 (14)	C14—N1—C10—C1	−76.6 (2)
O1—C2—C3—C4	−4.5 (3)	C11—N1—C10—C1	107.9 (2)
C1—C2—C3—C4	173.66 (17)	C14—N1—C10—C9	103.9 (2)
O1—C2—C3—C8	177.06 (19)	C11—N1—C10—C9	−71.6 (2)
C1—C2—C3—C8	−4.8 (3)	O2—C9—C10—C1	174.07 (19)
C8—C3—C4—C5	0.5 (3)	C8—C9—C10—C1	−6.1 (3)
C2—C3—C4—C5	−177.96 (17)	O2—C9—C10—N1	−6.5 (3)
C3—C4—C5—C6	−0.5 (3)	C8—C9—C10—N1	173.41 (16)
C4—C5—C6—C7	−0.3 (3)	C14—N1—C11—O3	175.03 (18)
C5—C6—C7—C8	1.1 (3)	C10—N1—C11—O3	−9.8 (2)
C6—C7—C8—C3	−1.0 (3)	C14—N1—C11—C12	−6.9 (3)
C6—C7—C8—C9	178.09 (18)	C10—N1—C11—C12	168.24 (17)
C4—C3—C8—C7	0.2 (3)	O3—C11—C12—C13	6.7 (3)
C2—C3—C8—C7	178.70 (18)	N1—C11—C12—C13	−171.24 (19)
C4—C3—C8—C9	−178.88 (17)	C11—N1—C14—O4	−19.9 (3)
C2—C3—C8—C9	−0.4 (3)	C10—N1—C14—O4	165.21 (18)
C7—C8—C9—O2	6.6 (3)	C11—N1—C14—C15	158.81 (18)
C3—C8—C9—O2	−174.25 (19)	C10—N1—C14—C15	−16.0 (2)
C7—C8—C9—C10	−173.25 (17)	O4—C14—C15—C16	3.9 (3)
C3—C8—C9—C10	5.9 (3)	N1—C14—C15—C16	−174.85 (18)
C2—C1—C10—N1	−178.69 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O3i	0.95	2.59	3.294 (2)	131
C15—H15A···O1ii	0.99	2.55	3.442 (2)	150
C16—H16B···O4iii	0.98	2.54	3.425 (3)	150
C16—H16C···O3iv	0.98	2.60	3.482 (3)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O3i	0.95	2.59	3.294 (2)	131
C15—H15A⋯O1ii	0.99	2.55	3.442 (2)	150
C16—H16B⋯O4iii	0.98	2.54	3.425 (3)	150
C16—H16C⋯O3iv	0.98	2.60	3.482 (3)	150

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .