N-(1,4-Dioxo-1,4-dihydro-naphthalen-2-yl)benzamide.

The title compound, C(17)H(11)NO(3), was an inter-mediate synthesized during bis-acyl-ation of 2-amino-1,4-naphtho-quinone with benzoyl chloride. A mixture of block- and needle-shaped crystals were obtained after column chromatography. The block-shaped crystals were identified as the imide and the needles were the title amide. The naphtho-quinone scaffold is roughly planar (r.m.s. deviation = 0.047 Å for the C atoms). The N-H and C=O bonds of the amide group are anti to each other. A dihedral angle between the naphtho-quinone ring system and the amide group of 3.56 (3)°, accompanied by a dihedral angle between the amide group and the phenyl group of 9.51 (3)°, makes the naphtho-quinone ring essentially coplanar with the phenyl ring [dihedral angle = 7.12 (1)°]. In the crystal, molecules are linked by a weak N-H⋯O hydrogen bond and by two weak C-H⋯O interactions leading to the formation of zigzag chains along [010].

Related literature

For similar crystal structures, see: Brandy et al. (2009 ▶, 2012 ▶); Akinboye et al. (2009a ▶,b ▶). For the pharmacological properties of related compounds, see: Bakare et al. (2003 ▶); Berhe et al. (2008 ▶); Lien et al. (1997 ▶); Huang, et al. (2005 ▶); Khraiwesh et al. (2011 ▶).

Experimental

Crystal data

C17H11NO3

M = 277.27

Monoclinic,

a = 6.9433 (3) Å

b = 12.0112 (4) Å

c = 15.2129 (5) Å

β = 94.129 (3)°

V = 1265.42 (8) Å3

Z = 4

Cu Kα radiation

μ = 0.83 mm−1

T = 123 K

0.67 × 0.12 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 ▶) T min = 0.819, T max = 1.000

4550 measured reflections

2553 independent reflections

2123 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.148

S = 1.05

2553 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); 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/S1600536812034150/bt5965sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034150/bt5965Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812034150/bt5965Isup3.cml

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

C17H11NO3	F(000) = 576
Mr = 277.27	Dx = 1.455 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
a = 6.9433 (3) Å	Cell parameters from 1585 reflections
b = 12.0112 (4) Å	θ = 2.9–75.6°
c = 15.2129 (5) Å	µ = 0.83 mm−1
β = 94.129 (3)°	T = 123 K
V = 1265.42 (8) Å3	Needle, pale yellow orange
Z = 4	0.67 × 0.12 × 0.08 mm

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2553 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2123 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
Detector resolution: 10.5081 pixels mm-1	θmax = 75.7°, θmin = 4.7°
ω scans	h = −7→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −14→14
Tmin = 0.819, Tmax = 1.000	l = −18→18
4550 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0937P)2] where P = (Fo2 + 2Fc2)/3
2553 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.25 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
O1	0.4411 (2)	0.09807 (11)	0.24463 (8)	0.0373 (3)
O2	0.3847 (2)	0.51857 (10)	0.13486 (8)	0.0348 (3)
O3	0.3674 (2)	0.41588 (11)	0.43416 (8)	0.0354 (3)
N1	0.3825 (2)	0.24883 (12)	0.36581 (9)	0.0273 (3)
H1A	0.3821	0.1763	0.3741	0.033*
C1	0.3905 (2)	0.28621 (14)	0.27989 (10)	0.0253 (4)
C2	0.4119 (2)	0.19196 (14)	0.21661 (10)	0.0269 (4)
C3	0.3957 (2)	0.21822 (14)	0.12102 (10)	0.0252 (4)
C4	0.3886 (2)	0.13177 (15)	0.05992 (11)	0.0299 (4)
H4A	0.3960	0.0566	0.0793	0.036*
C5	0.3707 (2)	0.15588 (15)	−0.02938 (11)	0.0314 (4)
H5A	0.3629	0.0971	−0.0713	0.038*
C6	0.3641 (2)	0.26586 (16)	−0.05777 (11)	0.0320 (4)
H6A	0.3547	0.2820	−0.1191	0.038*
C7	0.3713 (2)	0.35219 (15)	0.00297 (11)	0.0290 (4)
H7A	0.3670	0.4272	−0.0168	0.035*
C8	0.3848 (2)	0.32888 (14)	0.09291 (10)	0.0251 (4)
C9	0.3872 (2)	0.42102 (14)	0.15843 (10)	0.0266 (4)
C10	0.3855 (2)	0.39248 (14)	0.25204 (10)	0.0270 (4)
H10A	0.3807	0.4506	0.2942	0.032*
C11	0.3750 (2)	0.31531 (14)	0.43956 (10)	0.0261 (3)
C12	0.3814 (2)	0.25771 (14)	0.52731 (10)	0.0252 (4)
C13	0.4058 (2)	0.32638 (15)	0.60106 (11)	0.0294 (4)
H13A	0.4142	0.4047	0.5938	0.035*
C14	0.4181 (3)	0.28079 (16)	0.68528 (11)	0.0324 (4)
H14A	0.4353	0.3279	0.7354	0.039*
C15	0.4050 (2)	0.16642 (16)	0.69612 (11)	0.0316 (4)
H15A	0.4137	0.1352	0.7536	0.038*
C16	0.3794 (2)	0.09777 (15)	0.62296 (11)	0.0308 (4)
H16A	0.3694	0.0195	0.6306	0.037*
C17	0.3681 (2)	0.14279 (15)	0.53839 (11)	0.0286 (4)
H17A	0.3514	0.0954	0.4884	0.034*

	U11	U22	U33	U12	U13	U23
O1	0.0618 (8)	0.0246 (7)	0.0265 (6)	0.0064 (6)	0.0101 (5)	0.0045 (5)
O2	0.0576 (7)	0.0236 (6)	0.0238 (6)	−0.0019 (5)	0.0080 (5)	0.0045 (5)
O3	0.0604 (8)	0.0235 (6)	0.0221 (6)	0.0007 (5)	0.0030 (5)	0.0025 (5)
N1	0.0412 (7)	0.0216 (7)	0.0196 (7)	0.0017 (5)	0.0047 (5)	0.0045 (5)
C1	0.0299 (7)	0.0271 (8)	0.0192 (7)	0.0005 (6)	0.0037 (5)	0.0022 (6)
C2	0.0352 (7)	0.0234 (8)	0.0226 (8)	0.0011 (6)	0.0057 (6)	0.0038 (6)
C3	0.0302 (7)	0.0258 (8)	0.0202 (7)	−0.0002 (6)	0.0059 (5)	0.0011 (6)
C4	0.0380 (8)	0.0253 (8)	0.0271 (8)	−0.0008 (6)	0.0084 (6)	−0.0007 (6)
C5	0.0392 (8)	0.0315 (9)	0.0241 (8)	0.0001 (7)	0.0060 (6)	−0.0057 (7)
C6	0.0365 (8)	0.0393 (10)	0.0208 (7)	0.0005 (7)	0.0057 (6)	0.0008 (7)
C7	0.0369 (8)	0.0294 (9)	0.0211 (8)	0.0007 (7)	0.0054 (6)	0.0035 (6)
C8	0.0288 (7)	0.0260 (9)	0.0208 (7)	0.0001 (6)	0.0042 (5)	0.0025 (6)
C9	0.0349 (7)	0.0239 (8)	0.0214 (7)	−0.0006 (6)	0.0043 (6)	0.0037 (6)
C10	0.0378 (8)	0.0250 (8)	0.0184 (7)	−0.0014 (6)	0.0041 (6)	0.0010 (6)
C11	0.0325 (7)	0.0265 (8)	0.0195 (7)	0.0004 (6)	0.0027 (6)	0.0029 (6)
C12	0.0289 (7)	0.0270 (8)	0.0201 (8)	0.0007 (6)	0.0037 (6)	0.0046 (6)
C13	0.0373 (8)	0.0286 (9)	0.0227 (8)	0.0001 (6)	0.0045 (6)	0.0017 (6)
C14	0.0403 (9)	0.0382 (10)	0.0191 (7)	−0.0006 (7)	0.0048 (6)	−0.0015 (6)
C15	0.0351 (8)	0.0412 (10)	0.0187 (7)	0.0001 (7)	0.0032 (6)	0.0077 (7)
C16	0.0390 (8)	0.0287 (9)	0.0247 (8)	−0.0003 (7)	0.0034 (6)	0.0070 (7)
C17	0.0373 (8)	0.0282 (9)	0.0202 (7)	0.0002 (6)	0.0024 (6)	0.0017 (6)

O1—C2	1.217 (2)	C7—C8	1.393 (2)
O2—C9	1.225 (2)	C7—H7A	0.9500
O3—C11	1.212 (2)	C8—C9	1.489 (2)
N1—C11	1.381 (2)	C9—C10	1.466 (2)
N1—C1	1.3869 (19)	C10—H10A	0.9500
N1—H1A	0.8800	C11—C12	1.501 (2)
C1—C10	1.345 (2)	C12—C13	1.393 (2)
C1—C2	1.500 (2)	C12—C17	1.394 (2)
C2—C3	1.484 (2)	C13—C14	1.390 (2)
C3—C4	1.392 (2)	C13—H13A	0.9500
C3—C8	1.397 (2)	C14—C15	1.387 (3)
C4—C5	1.386 (2)	C14—H14A	0.9500
C4—H4A	0.9500	C15—C16	1.386 (3)
C5—C6	1.390 (3)	C15—H15A	0.9500
C5—H5A	0.9500	C16—C17	1.393 (2)
C6—C7	1.387 (2)	C16—H16A	0.9500
C6—H6A	0.9500	C17—H17A	0.9500
C11—N1—C1	125.79 (14)	O2—C9—C10	120.48 (15)
C11—N1—H1A	117.1	O2—C9—C8	121.05 (14)
C1—N1—H1A	117.1	C10—C9—C8	118.44 (14)
C10—C1—N1	127.04 (15)	C1—C10—C9	121.76 (15)
C10—C1—C2	121.04 (14)	C1—C10—H10A	119.1
N1—C1—C2	111.90 (14)	C9—C10—H10A	119.1
O1—C2—C3	122.60 (16)	O3—C11—N1	121.69 (14)
O1—C2—C1	119.73 (14)	O3—C11—C12	121.20 (15)
C3—C2—C1	117.67 (14)	N1—C11—C12	117.10 (15)
C4—C3—C8	120.45 (15)	C13—C12—C17	119.61 (14)
C4—C3—C2	119.49 (15)	C13—C12—C11	115.94 (15)
C8—C3—C2	120.05 (15)	C17—C12—C11	124.45 (15)
C5—C4—C3	119.67 (16)	C14—C13—C12	120.32 (16)
C5—C4—H4A	120.2	C14—C13—H13A	119.8
C3—C4—H4A	120.2	C12—C13—H13A	119.8
C4—C5—C6	120.13 (16)	C15—C14—C13	119.96 (16)
C4—C5—H5A	119.9	C15—C14—H14A	120.0
C6—C5—H5A	119.9	C13—C14—H14A	120.0
C7—C6—C5	120.31 (15)	C16—C15—C14	119.95 (15)
C7—C6—H6A	119.8	C16—C15—H15A	120.0
C5—C6—H6A	119.8	C14—C15—H15A	120.0
C6—C7—C8	120.04 (16)	C15—C16—C17	120.41 (17)
C6—C7—H7A	120.0	C15—C16—H16A	119.8
C8—C7—H7A	120.0	C17—C16—H16A	119.8
C7—C8—C3	119.36 (16)	C16—C17—C12	119.75 (16)
C7—C8—C9	120.32 (15)	C16—C17—H17A	120.1
C3—C8—C9	120.32 (14)	C12—C17—H17A	120.1
C11—N1—C1—C10	−2.6 (3)	C3—C8—C9—O2	177.33 (15)
C11—N1—C1—C2	175.82 (14)	C7—C8—C9—C10	175.06 (14)
C10—C1—C2—O1	170.53 (16)	C3—C8—C9—C10	−4.8 (2)
N1—C1—C2—O1	−8.0 (2)	N1—C1—C10—C9	−177.44 (15)
C10—C1—C2—C3	−9.6 (2)	C2—C1—C10—C9	4.3 (2)
N1—C1—C2—C3	171.88 (13)	O2—C9—C10—C1	−179.15 (15)
O1—C2—C3—C4	8.5 (2)	C8—C9—C10—C1	3.0 (2)
C1—C2—C3—C4	−171.42 (14)	C1—N1—C11—O3	2.9 (3)
O1—C2—C3—C8	−172.50 (15)	C1—N1—C11—C12	−175.70 (14)
C1—C2—C3—C8	7.6 (2)	O3—C11—C12—C13	−8.8 (2)
C8—C3—C4—C5	0.1 (2)	N1—C11—C12—C13	169.78 (14)
C2—C3—C4—C5	179.07 (15)	O3—C11—C12—C17	172.36 (16)
C3—C4—C5—C6	1.4 (3)	N1—C11—C12—C17	−9.0 (2)
C4—C5—C6—C7	−1.4 (2)	C17—C12—C13—C14	0.4 (2)
C5—C6—C7—C8	−0.1 (2)	C11—C12—C13—C14	−178.52 (15)
C6—C7—C8—C3	1.6 (2)	C12—C13—C14—C15	−0.3 (2)
C6—C7—C8—C9	−178.34 (14)	C13—C14—C15—C16	−0.2 (3)
C4—C3—C8—C7	−1.5 (2)	C14—C15—C16—C17	0.5 (3)
C2—C3—C8—C7	179.46 (14)	C15—C16—C17—C12	−0.5 (2)
C4—C3—C8—C9	178.37 (14)	C13—C12—C17—C16	0.0 (2)
C2—C3—C8—C9	−0.6 (2)	C11—C12—C17—C16	178.79 (15)
C7—C8—C9—O2	−2.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.88	2.65	3.3299 (19)	135
C4—H4A···O3i	0.95	2.49	3.149 (2)	127
C17—H17A···O2i	0.95	2.57	3.404 (2)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.88	2.65	3.3299 (19)	135
C4—H4A⋯O3i	0.95	2.49	3.149 (2)	127
C17—H17A⋯O2i	0.95	2.57	3.404 (2)	146

Symmetry code: (i) .