N-Butanoyl-N-(3-chloro-1,4-dioxonaph-thalen-2-yl)butanamide.

In the title compound, C18H18ClNO4, the imide group with its two alkyl substituents is approximately perpendicular to the plane of the naphtho-quinone ring system [dihedral angle = 78.5 (1)°]. Further, the imide carbonyl groups are oriented in an anti sense. In the crystal, the substituted naphtho-quinone rings form π-π stacks in the a-axis direction [perpendicular centroid-centroid distance = 3.209 (2) Å and slippage = 4.401 Å].

Related literature

For the synthesis and biological evaluation of some imido-substituted 1,4-naphtho­quinone derivatives, see; Bakare et al. (2003 ▶); Berhe et al. (2008 ▶); Brandy et al. (2013 ▶). For the anti-cancer and anti-trypanosomal activity of the title compound, see; Bakare et al. (2003 ▶); Berhe et al. (2008 ▶); Khraiwesh et al. (2012 ▶).

Experimental

Crystal data

C18H18ClNO4

M = 347.78

Triclinic,

a = 8.1717 (10) Å

b = 8.3117 (10) Å

c = 14.6841 (15) Å

α = 93.119 (9)°

β = 98.369 (10)°

γ = 118.043 (12)°

V = 862.23 (17) Å3

Z = 2

Cu Kα radiation

μ = 2.15 mm−1

T = 295 K

0.36 × 0.28 × 0.08 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.530, T max = 1.000

5454 measured reflections

3398 independent reflections

2122 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.077

wR(F 2) = 0.227

S = 1.12

3398 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.24 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, global. DOI: 10.1107/S1600536813016401/hg5322sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016401/hg5322Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813016401/hg5322Isup3.cml

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

C18H18ClNO4	Z = 2
Mr = 347.78	F(000) = 364
Triclinic, P1	Dx = 1.340 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 8.1717 (10) Å	Cell parameters from 1350 reflections
b = 8.3117 (10) Å	θ = 3.1–75.5°
c = 14.6841 (15) Å	µ = 2.15 mm−1
α = 93.119 (9)°	T = 295 K
β = 98.369 (10)°	Plate, pale yellow
γ = 118.043 (12)°	0.36 × 0.28 × 0.08 mm
V = 862.23 (17) Å3

Agilent Xcalibur (Ruby, Gemini) diffractometer	3398 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2122 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
Detector resolution: 10.5081 pixels mm-1	θmax = 75.7°, θmin = 3.1°
ω scans	h = −8→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −10→8
Tmin = 0.530, Tmax = 1.000	l = −18→18
5454 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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.227	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0739P)2 + 0.4803P] where P = (Fo2 + 2Fc2)/3
3398 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.24 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	0.4121 (2)	0.34538 (16)	0.17915 (8)	0.0891 (4)
O1	0.2762 (5)	0.3535 (4)	−0.0134 (2)	0.0844 (9)
O2	0.4177 (5)	0.9507 (4)	0.2097 (2)	0.0938 (11)
O3	0.7195 (7)	0.7372 (8)	0.4060 (3)	0.1463 (19)
O4	0.1712 (5)	0.5863 (5)	0.3023 (2)	0.0968 (11)
N1	0.4736 (5)	0.6864 (5)	0.2928 (2)	0.0706 (9)
C1	0.3740 (6)	0.5151 (5)	0.1381 (3)	0.0639 (10)
C2	0.2990 (6)	0.4877 (5)	0.0361 (3)	0.0662 (10)
C3	0.2519 (6)	0.6265 (5)	0.0005 (2)	0.0607 (9)
C4	0.1688 (6)	0.6021 (6)	−0.0927 (3)	0.0722 (11)
H4A	0.1453	0.4994	−0.1325	0.087*
C5	0.1217 (7)	0.7286 (7)	−0.1261 (3)	0.0855 (13)
H5A	0.0661	0.7112	−0.1883	0.103*
C6	0.1562 (8)	0.8814 (7)	−0.0680 (3)	0.0886 (14)
H6A	0.1230	0.9664	−0.0909	0.106*
C7	0.2399 (7)	0.9083 (6)	0.0240 (3)	0.0785 (12)
H7A	0.2649	1.0126	0.0628	0.094*
C8	0.2869 (6)	0.7820 (5)	0.0590 (2)	0.0622 (9)
C9	0.3728 (6)	0.8109 (5)	0.1584 (3)	0.0680 (10)
C10	0.4067 (6)	0.6633 (5)	0.1942 (2)	0.0622 (10)
C11	0.6690 (8)	0.7503 (8)	0.3266 (3)	0.0961 (16)
C12	0.7987 (8)	0.8295 (9)	0.2605 (4)	0.1059 (18)
H12A	0.7738	0.9213	0.2331	0.127*
H12B	0.7675	0.7323	0.2108	0.127*
C13	1.0076 (11)	0.9175 (12)	0.2999 (6)	0.142 (3)
H13A	1.0310	0.8316	0.3343	0.171*
H13B	1.0747	0.9385	0.2487	0.171*
C14	1.0836 (12)	1.0872 (13)	0.3596 (6)	0.174 (4)
H14A	1.2123	1.1256	0.3876	0.261*
H14B	1.0106	1.0712	0.4073	0.261*
H14C	1.0791	1.1792	0.3241	0.261*
C15	0.3333 (8)	0.6480 (7)	0.3445 (3)	0.0796 (12)
C16	0.3897 (9)	0.6902 (10)	0.4493 (3)	0.1102 (19)
H16A	0.4304	0.6045	0.4716	0.132*
H16B	0.4976	0.8129	0.4656	0.132*
C17	0.2496 (10)	0.6815 (14)	0.4964 (4)	0.149 (3)
H17A	0.1405	0.5600	0.4784	0.179*
H17B	0.2116	0.7696	0.4751	0.179*
C18	0.2999 (10)	0.7179 (11)	0.6009 (4)	0.131 (2)
H18A	0.1924	0.7052	0.6254	0.197*
H18B	0.4029	0.8406	0.6204	0.197*
H18C	0.3366	0.6311	0.6236	0.197*

	U11	U22	U33	U12	U13	U23
Cl1	0.1260 (11)	0.0735 (7)	0.0734 (7)	0.0587 (7)	0.0014 (6)	0.0018 (5)
O1	0.118 (3)	0.0700 (17)	0.0620 (16)	0.0477 (18)	0.0066 (16)	−0.0132 (13)
O2	0.142 (3)	0.0725 (18)	0.0629 (17)	0.061 (2)	−0.0114 (18)	−0.0161 (14)
O3	0.135 (4)	0.212 (5)	0.079 (3)	0.083 (4)	−0.015 (2)	0.023 (3)
O4	0.100 (3)	0.121 (3)	0.0619 (18)	0.048 (2)	0.0175 (18)	−0.0028 (18)
N1	0.087 (2)	0.074 (2)	0.0479 (16)	0.0428 (19)	−0.0014 (16)	−0.0036 (14)
C1	0.075 (3)	0.058 (2)	0.057 (2)	0.0337 (19)	0.0084 (18)	0.0011 (16)
C2	0.076 (3)	0.062 (2)	0.052 (2)	0.028 (2)	0.0118 (18)	−0.0076 (16)
C3	0.065 (2)	0.062 (2)	0.0489 (18)	0.0283 (18)	0.0065 (16)	−0.0022 (15)
C4	0.083 (3)	0.077 (3)	0.048 (2)	0.035 (2)	0.0066 (19)	−0.0033 (18)
C5	0.098 (3)	0.096 (3)	0.055 (2)	0.046 (3)	0.000 (2)	0.008 (2)
C6	0.111 (4)	0.087 (3)	0.070 (3)	0.053 (3)	0.003 (3)	0.015 (2)
C7	0.101 (3)	0.069 (2)	0.063 (2)	0.045 (2)	0.001 (2)	−0.0012 (19)
C8	0.071 (2)	0.061 (2)	0.0501 (19)	0.0311 (19)	0.0041 (17)	0.0001 (15)
C9	0.084 (3)	0.061 (2)	0.052 (2)	0.034 (2)	0.0034 (18)	−0.0068 (16)
C10	0.073 (3)	0.062 (2)	0.0454 (18)	0.0316 (19)	0.0012 (16)	−0.0035 (15)
C11	0.109 (4)	0.107 (4)	0.064 (3)	0.057 (3)	−0.016 (3)	−0.006 (3)
C12	0.087 (4)	0.125 (5)	0.084 (3)	0.039 (3)	0.005 (3)	−0.009 (3)
C13	0.128 (6)	0.169 (7)	0.131 (6)	0.084 (6)	−0.009 (5)	0.007 (5)
C14	0.145 (7)	0.175 (8)	0.126 (6)	0.035 (6)	−0.032 (5)	0.002 (6)
C15	0.101 (4)	0.087 (3)	0.054 (2)	0.052 (3)	0.003 (2)	−0.003 (2)
C16	0.131 (5)	0.149 (5)	0.056 (3)	0.075 (4)	0.011 (3)	0.001 (3)
C17	0.131 (5)	0.253 (9)	0.055 (3)	0.090 (6)	0.014 (3)	−0.003 (4)
C18	0.140 (6)	0.185 (7)	0.057 (3)	0.072 (5)	0.015 (3)	−0.002 (4)

Cl1—C1	1.703 (4)	C9—C10	1.484 (5)
O1—C2	1.218 (4)	C11—C12	1.487 (8)
O2—C9	1.215 (4)	C12—C13	1.508 (8)
O3—C11	1.207 (6)	C12—H12A	0.9700
O4—C15	1.221 (6)	C12—H12B	0.9700
N1—C15	1.389 (6)	C13—C14	1.424 (10)
N1—C11	1.422 (6)	C13—H13A	0.9700
N1—C10	1.440 (4)	C13—H13B	0.9700
C1—C10	1.335 (5)	C14—H14A	0.9600
C1—C2	1.496 (5)	C14—H14B	0.9600
C2—C3	1.475 (6)	C14—H14C	0.9600
C3—C4	1.395 (5)	C15—C16	1.512 (6)
C3—C8	1.397 (5)	C16—C17	1.397 (8)
C4—C5	1.369 (6)	C16—H16A	0.9700
C4—H4A	0.9300	C16—H16B	0.9700
C5—C6	1.377 (7)	C17—C18	1.505 (7)
C5—H5A	0.9300	C17—H17A	0.9700
C6—C7	1.377 (6)	C17—H17B	0.9700
C6—H6A	0.9300	C18—H18A	0.9600
C7—C8	1.376 (6)	C18—H18B	0.9600
C7—H7A	0.9300	C18—H18C	0.9600
C8—C9	1.479 (5)
C15—N1—C11	127.5 (4)	C13—C12—H12A	108.1
C15—N1—C10	113.5 (4)	C11—C12—H12B	108.1
C11—N1—C10	119.0 (4)	C13—C12—H12B	108.1
C10—C1—C2	121.8 (4)	H12A—C12—H12B	107.3
C10—C1—Cl1	121.9 (3)	C14—C13—C12	114.9 (7)
C2—C1—Cl1	116.3 (3)	C14—C13—H13A	108.5
O1—C2—C3	122.9 (4)	C12—C13—H13A	108.5
O1—C2—C1	120.0 (4)	C14—C13—H13B	108.5
C3—C2—C1	117.0 (3)	C12—C13—H13B	108.5
C4—C3—C8	119.0 (4)	H13A—C13—H13B	107.5
C4—C3—C2	119.9 (3)	C13—C14—H14A	109.5
C8—C3—C2	121.1 (3)	C13—C14—H14B	109.5
C5—C4—C3	120.4 (4)	H14A—C14—H14B	109.5
C5—C4—H4A	119.8	C13—C14—H14C	109.5
C3—C4—H4A	119.8	H14A—C14—H14C	109.5
C4—C5—C6	120.4 (4)	H14B—C14—H14C	109.5
C4—C5—H5A	119.8	O4—C15—N1	117.7 (4)
C6—C5—H5A	119.8	O4—C15—C16	123.7 (5)
C5—C6—C7	119.9 (4)	N1—C15—C16	118.6 (5)
C5—C6—H6A	120.0	C17—C16—C15	115.8 (5)
C7—C6—H6A	120.0	C17—C16—H16A	108.3
C8—C7—C6	120.6 (4)	C15—C16—H16A	108.3
C8—C7—H7A	119.7	C17—C16—H16B	108.3
C6—C7—H7A	119.7	C15—C16—H16B	108.3
C7—C8—C3	119.8 (4)	H16A—C16—H16B	107.4
C7—C8—C9	119.9 (3)	C16—C17—C18	117.0 (6)
C3—C8—C9	120.3 (4)	C16—C17—H17A	108.1
O2—C9—C8	122.0 (4)	C18—C17—H17A	108.1
O2—C9—C10	120.3 (4)	C16—C17—H17B	108.1
C8—C9—C10	117.6 (3)	C18—C17—H17B	108.1
C1—C10—N1	121.5 (4)	H17A—C17—H17B	107.3
C1—C10—C9	121.9 (3)	C17—C18—H18A	109.5
N1—C10—C9	116.6 (3)	C17—C18—H18B	109.5
O3—C11—N1	118.8 (6)	H18A—C18—H18B	109.5
O3—C11—C12	124.2 (6)	C17—C18—H18C	109.5
N1—C11—C12	117.0 (4)	H18A—C18—H18C	109.5
C11—C12—C13	116.7 (5)	H18B—C18—H18C	109.5
C11—C12—H12A	108.1
C10—C1—C2—O1	177.8 (4)	C2—C1—C10—C9	−0.7 (6)
Cl1—C1—C2—O1	−3.1 (6)	Cl1—C1—C10—C9	−179.8 (3)
C10—C1—C2—C3	−3.5 (6)	C15—N1—C10—C1	−102.5 (5)
Cl1—C1—C2—C3	175.6 (3)	C11—N1—C10—C1	79.8 (5)
O1—C2—C3—C4	3.2 (6)	C15—N1—C10—C9	76.4 (5)
C1—C2—C3—C4	−175.4 (4)	C11—N1—C10—C9	−101.2 (5)
O1—C2—C3—C8	−177.6 (4)	O2—C9—C10—C1	−174.2 (4)
C1—C2—C3—C8	3.7 (6)	C8—C9—C10—C1	4.7 (6)
C8—C3—C4—C5	−0.3 (7)	O2—C9—C10—N1	6.8 (6)
C2—C3—C4—C5	178.9 (4)	C8—C9—C10—N1	−174.3 (4)
C3—C4—C5—C6	0.1 (8)	C15—N1—C11—O3	16.4 (8)
C4—C5—C6—C7	0.5 (8)	C10—N1—C11—O3	−166.3 (5)
C5—C6—C7—C8	−1.1 (8)	C15—N1—C11—C12	−163.7 (5)
C6—C7—C8—C3	0.9 (7)	C10—N1—C11—C12	13.6 (7)
C6—C7—C8—C9	−178.6 (5)	O3—C11—C12—C13	−7.2 (10)
C4—C3—C8—C7	−0.3 (6)	N1—C11—C12—C13	172.9 (5)
C2—C3—C8—C7	−179.4 (4)	C11—C12—C13—C14	−70.9 (9)
C4—C3—C8—C9	179.3 (4)	C11—N1—C15—O4	−176.9 (4)
C2—C3—C8—C9	0.1 (6)	C10—N1—C15—O4	5.7 (6)
C7—C8—C9—O2	−5.9 (7)	C11—N1—C15—C16	5.1 (7)
C3—C8—C9—O2	174.5 (4)	C10—N1—C15—C16	−172.3 (4)
C7—C8—C9—C10	175.3 (4)	O4—C15—C16—C17	−9.5 (10)
C3—C8—C9—C10	−4.3 (6)	N1—C15—C16—C17	168.4 (6)
C2—C1—C10—N1	178.2 (4)	C15—C16—C17—C18	178.4 (7)
Cl1—C1—C10—N1	−0.9 (6)