2-Nitro-N-(8-quinolyl)benzamide

Lei, G.; Jing, L.-H.; Zhou, L.

doi:10.1107/S160053680803777X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2392

doi:10.1107/S160053680803777X

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2-Nitro-N-(8-quinolyl)benzamide

Gang Lei,^a ^* Lin-Hai Jing ^a and Li Zhou ^a

^aSchool of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: leigang307@yahoo.com.cn

(Received 13 November 2008; accepted 14 November 2008; online 20 November 2008)

In the title compound, C₁₆H₁₁N₃O₃, the amide group is twisted away from the quinoline ring system and nitrobenzene ring by 8.02 (1)° and 54.92 (1)°, respectively. The crystal packing is stabilized by intermolecular C—H⋯O hydrogen bonds, and π–π interactions between the quinoline ring systems of inversion-related molecules, with a centroid–centroid distance of 3.4802 (13) Å.

Related literature

For the biological activities of quinoline derivatives, see: Oku et al. (1998 , 1999 ).

Experimental

Crystal data

C₁₆H₁₁N₃O₃
M_r = 293.28
Monoclinic, P 2₁ /c
a = 12.430 (3) Å
b = 10.144 (3) Å
c = 11.528 (3) Å
β = 116.449 (3)°
V = 1301.4 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 93 (2) K
0.50 × 0.40 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: none
10410 measured reflections
2949 independent reflections
2679 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.145
S = 1.00
2949 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3ⁱ	0.95	2.55	3.209 (2)	127
C4—H4⋯O2ⁱⁱ	0.95	2.48	3.319 (2)	147
C17—H17⋯O1ⁱⁱⁱ	0.95	2.42	3.160 (2)	135
Symmetry codes: (i) x-1, y, z-1; (ii) -x, -y+1, -z+1; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 2004 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803777X/ci2716sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680803777X/ci2716Isup2.hkl

checkCIF report

Comment top

Quinoline derivatives are a class of important compound for the treatment of bone metabolic disorders (Oku et al., 1998) and as H⁺-ATPases inhibitors (Oku et al., 1999). We report here the crystal structure of the title compound.

Bond lengths and angles in title molecule (Fig.1) are normal. The quinoline ring system is planar, with a maximum deviation of 0.033 (2) Å for atom C3. As a result of steric effects, the amide group is twisted away from the planes of the quinoline ring system and the nitrobenzene ring. The C5-C10 and C12-C17 planes form dihedral angles of 8.02 (1) and 54.92 (1)°, respectively, with the O1/N2/C8/C11 plane. The dihedral angle between the C12-C17 and O2/O3/N3/C13 planes is 36.83 (1)°.

The crystal packing is stabilized by C—H···O hydrogen bonds (Table 1), and π-π interactions between the benzene rings of the inversion-related molecules at (x, y, z) and (-x, 1 - y, 1 - z), with a centroid-centroid distance of 3.4802 (13) Å.

Related literature top

For the biological activities of quinoline derivatives, see: Oku et al. (1998, 1999).

Experimental top

O-Nitrobenzoic acid (2 mmol) and an excess of thionyl chloride (3 mmol) in dioxane (20 ml) were boiled under reflux for 6 h. The solution was distilled under reduced pressure and a yellow solid was obtained. 8-Aminoquinoline (2 mmol) in tetrahydrofuran (20 ml) was added to the yellow solid and boiled under reflux for 6 h. The solution was then cooled to ambient temperature and filtered to remove the tetrahydrofuran. The precipitate was dissolved in the dimethyl sulfoxide and allowed to stand for one month at ambient temperature, after which time white single crystals of the title compound suitable for X-ray diffraction were obtained.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO (Rigaku, 2004); data reduction: RAPID-AUTO (Rigaku, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering.

2-Nitro-N-(8-quinolyl)benzamide top

Crystal data top

C₁₆H₁₁N₃O₃	F(000) = 608
M_r = 293.28	D_x = 1.497 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3984 reflections
a = 12.430 (3) Å	θ = 3.2–27.5°
b = 10.144 (3) Å	µ = 0.11 mm⁻¹
c = 11.528 (3) Å	T = 93 K
β = 116.449 (3)°	Block, white
V = 1301.4 (6) Å³	0.50 × 0.40 × 0.15 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	2679 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.029
Graphite monochromator	θ_max = 27.5°, θ_min = 3.5°
ω scans	h = −16→16
10410 measured reflections	k = −12→13
2949 independent reflections	l = −14→11

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.089P)² + 0.36P] where P = (F_o² + 2F_c²)/3
2949 reflections	(Δ/σ)_max = 0.005
199 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₆H₁₁N₃O₃	V = 1301.4 (6) Å³
M_r = 293.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.430 (3) Å	µ = 0.11 mm⁻¹
b = 10.144 (3) Å	T = 93 K
c = 11.528 (3) Å	0.50 × 0.40 × 0.15 mm
β = 116.449 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	2679 reflections with I > 2σ(I)
10410 measured reflections	R_int = 0.029
2949 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.145	H-atom parameters constrained
S = 1.00	Δρ_max = 0.22 e Å⁻³
2949 reflections	Δρ_min = −0.28 e Å⁻³
199 parameters

Special details top

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
O1	0.33297 (10)	0.27884 (13)	0.71053 (11)	0.0283 (3)
O2	0.42529 (10)	0.55360 (12)	0.75700 (12)	0.0290 (3)
O3	0.60516 (11)	0.50766 (12)	0.90418 (11)	0.0291 (3)
N1	0.07416 (11)	0.46239 (13)	0.28513 (13)	0.0202 (3)
N2	0.23340 (11)	0.35402 (13)	0.50283 (13)	0.0201 (3)
H2N	0.2460	0.3835	0.4381	0.024*
N3	0.52329 (11)	0.49852 (13)	0.79419 (13)	0.0213 (3)
C2	−0.00265 (14)	0.52243 (15)	0.17885 (15)	0.0212 (3)
H2	0.0284	0.5671	0.1278	0.025*
C3	−0.12782 (14)	0.52428 (15)	0.13644 (16)	0.0223 (4)
H3	−0.1791	0.5691	0.0590	0.027*
C4	−0.17449 (14)	0.46062 (15)	0.20824 (16)	0.0221 (4)
H4	−0.2588	0.4591	0.1803	0.027*
C5	−0.13518 (14)	0.33419 (15)	0.40878 (16)	0.0210 (3)
H5	−0.2184	0.3298	0.3865	0.025*
C6	−0.05278 (14)	0.27986 (15)	0.52209 (16)	0.0215 (3)
H6	−0.0800	0.2388	0.5783	0.026*
C7	0.07210 (14)	0.28306 (15)	0.55819 (16)	0.0205 (3)
H7	0.1275	0.2441	0.6373	0.025*
C8	0.11263 (13)	0.34276 (14)	0.47822 (15)	0.0187 (3)
C9	0.02839 (13)	0.40129 (14)	0.35897 (15)	0.0181 (3)
C10	−0.09602 (13)	0.39701 (15)	0.32465 (15)	0.0194 (3)
C11	0.33334 (13)	0.32539 (15)	0.61325 (15)	0.0197 (3)
C12	0.44935 (13)	0.34895 (15)	0.60488 (14)	0.0184 (3)
C13	0.54399 (13)	0.41992 (15)	0.69958 (15)	0.0189 (3)
C14	0.65666 (14)	0.42618 (15)	0.70338 (16)	0.0220 (3)
H14	0.7198	0.4741	0.7698	0.026*
C15	0.67563 (14)	0.36117 (15)	0.60838 (17)	0.0243 (4)
H15	0.7527	0.3629	0.6100	0.029*
C16	0.58228 (15)	0.29374 (16)	0.51112 (16)	0.0239 (4)
H16	0.5951	0.2518	0.4447	0.029*
C17	0.47000 (14)	0.28663 (15)	0.50942 (15)	0.0216 (3)
H17	0.4070	0.2389	0.4426	0.026*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0213 (6)	0.0419 (7)	0.0199 (6)	−0.0011 (5)	0.0074 (5)	0.0064 (5)
O2	0.0197 (6)	0.0347 (7)	0.0308 (7)	0.0053 (5)	0.0098 (5)	−0.0042 (5)
O3	0.0255 (6)	0.0327 (7)	0.0207 (6)	−0.0014 (5)	0.0026 (5)	−0.0051 (5)
N1	0.0183 (6)	0.0203 (6)	0.0204 (7)	−0.0013 (5)	0.0073 (5)	0.0005 (5)
N2	0.0168 (6)	0.0242 (7)	0.0187 (7)	−0.0022 (5)	0.0074 (5)	0.0018 (5)
N3	0.0191 (6)	0.0210 (7)	0.0213 (7)	−0.0014 (5)	0.0067 (6)	−0.0016 (5)
C2	0.0218 (8)	0.0205 (7)	0.0200 (8)	−0.0014 (6)	0.0081 (6)	0.0023 (6)
C3	0.0201 (7)	0.0195 (7)	0.0229 (8)	0.0002 (6)	0.0056 (6)	0.0004 (6)
C4	0.0174 (7)	0.0197 (7)	0.0267 (9)	0.0012 (6)	0.0076 (6)	−0.0010 (6)
C5	0.0181 (7)	0.0197 (7)	0.0271 (8)	−0.0013 (6)	0.0118 (6)	−0.0031 (6)
C6	0.0244 (8)	0.0186 (7)	0.0259 (9)	−0.0027 (6)	0.0151 (7)	−0.0014 (6)
C7	0.0213 (8)	0.0188 (7)	0.0211 (8)	−0.0005 (6)	0.0092 (6)	−0.0016 (6)
C8	0.0169 (7)	0.0167 (7)	0.0216 (8)	−0.0023 (5)	0.0079 (6)	−0.0034 (6)
C9	0.0184 (7)	0.0156 (7)	0.0196 (8)	−0.0014 (5)	0.0078 (6)	−0.0024 (6)
C10	0.0184 (7)	0.0165 (7)	0.0219 (8)	−0.0010 (5)	0.0077 (6)	−0.0039 (6)
C11	0.0193 (7)	0.0199 (7)	0.0188 (8)	−0.0008 (6)	0.0076 (6)	−0.0015 (6)
C12	0.0171 (7)	0.0189 (7)	0.0165 (7)	0.0014 (5)	0.0050 (6)	0.0040 (5)
C13	0.0188 (7)	0.0181 (7)	0.0180 (8)	0.0014 (5)	0.0066 (6)	0.0013 (6)
C14	0.0165 (7)	0.0205 (7)	0.0259 (8)	−0.0006 (6)	0.0065 (6)	0.0007 (6)
C15	0.0216 (8)	0.0207 (7)	0.0328 (9)	0.0030 (6)	0.0140 (7)	0.0049 (7)
C16	0.0281 (8)	0.0219 (8)	0.0249 (9)	0.0015 (6)	0.0148 (7)	0.0021 (6)
C17	0.0225 (8)	0.0223 (8)	0.0189 (8)	−0.0012 (6)	0.0081 (6)	0.0009 (6)

Geometric parameters (Å, º) top

O1—C11	1.219 (2)	C6—C7	1.417 (2)
O2—N3	1.2307 (17)	C6—H6	0.95
O3—N3	1.2257 (17)	C7—C8	1.373 (2)
N1—C2	1.320 (2)	C7—H7	0.95
N1—C9	1.365 (2)	C8—C9	1.434 (2)
N2—C11	1.3562 (19)	C9—C10	1.416 (2)
N2—C8	1.4028 (19)	C11—C12	1.507 (2)
N2—H2N	0.88	C12—C17	1.389 (2)
N3—C13	1.463 (2)	C12—C13	1.396 (2)
C2—C3	1.408 (2)	C13—C14	1.383 (2)
C2—H2	0.95	C14—C15	1.386 (2)
C3—C4	1.366 (2)	C14—H14	0.95
C3—H3	0.95	C15—C16	1.383 (2)
C4—C10	1.415 (2)	C15—H15	0.95
C4—H4	0.95	C16—C17	1.389 (2)
C5—C6	1.366 (2)	C16—H16	0.95
C5—C10	1.416 (2)	C17—H17	0.95
C5—H5	0.95

C2—N1—C9	117.28 (13)	N1—C9—C10	123.11 (14)
C11—N2—C8	128.52 (13)	N1—C9—C8	117.16 (13)
C11—N2—H2N	115.7	C10—C9—C8	119.70 (14)
C8—N2—H2N	115.7	C4—C10—C5	123.56 (14)
O3—N3—O2	124.26 (14)	C4—C10—C9	117.17 (14)
O3—N3—C13	118.14 (13)	C5—C10—C9	119.23 (14)
O2—N3—C13	117.59 (13)	O1—C11—N2	124.71 (14)
N1—C2—C3	123.99 (15)	O1—C11—C12	121.09 (14)
N1—C2—H2	118.0	N2—C11—C12	114.12 (13)
C3—C2—H2	118.0	C17—C12—C13	117.75 (14)
C4—C3—C2	119.02 (15)	C17—C12—C11	119.90 (13)
C4—C3—H3	120.5	C13—C12—C11	121.93 (14)
C2—C3—H3	120.5	C14—C13—C12	122.48 (15)
C3—C4—C10	119.39 (14)	C14—C13—N3	117.59 (13)
C3—C4—H4	120.3	C12—C13—N3	119.80 (13)
C10—C4—H4	120.3	C13—C14—C15	118.66 (14)
C6—C5—C10	119.76 (14)	C13—C14—H14	120.7
C6—C5—H5	120.1	C15—C14—H14	120.7
C10—C5—H5	120.1	C16—C15—C14	119.96 (15)
C5—C6—C7	121.88 (15)	C16—C15—H15	120.0
C5—C6—H6	119.1	C14—C15—H15	120.0
C7—C6—H6	119.1	C15—C16—C17	120.81 (15)
C8—C7—C6	119.64 (15)	C15—C16—H16	119.6
C8—C7—H7	120.2	C17—C16—H16	119.6
C6—C7—H7	120.2	C12—C17—C16	120.29 (15)
C7—C8—N2	125.45 (14)	C12—C17—H17	119.9
C7—C8—C9	119.78 (14)	C16—C17—H17	119.9
N2—C8—C9	114.76 (13)

C9—N1—C2—C3	−1.5 (2)	C8—C9—C10—C5	−0.3 (2)
N1—C2—C3—C4	0.0 (2)	C8—N2—C11—O1	3.0 (3)
C2—C3—C4—C10	1.4 (2)	C8—N2—C11—C12	179.71 (14)
C10—C5—C6—C7	−0.7 (2)	O1—C11—C12—C17	120.18 (17)
C5—C6—C7—C8	0.4 (2)	N2—C11—C12—C17	−56.67 (19)
C6—C7—C8—N2	179.31 (14)	O1—C11—C12—C13	−52.2 (2)
C6—C7—C8—C9	0.0 (2)	N2—C11—C12—C13	130.96 (15)
C11—N2—C8—C7	−9.2 (3)	C17—C12—C13—C14	−2.1 (2)
C11—N2—C8—C9	170.17 (14)	C11—C12—C13—C14	170.39 (14)
C2—N1—C9—C10	1.7 (2)	C17—C12—C13—N3	173.65 (13)
C2—N1—C9—C8	−176.46 (14)	C11—C12—C13—N3	−13.8 (2)
C7—C8—C9—N1	178.25 (13)	O3—N3—C13—C14	−37.9 (2)
N2—C8—C9—N1	−1.14 (19)	O2—N3—C13—C14	140.59 (15)
C7—C8—C9—C10	0.0 (2)	O3—N3—C13—C12	146.16 (15)
N2—C8—C9—C10	−179.40 (13)	O2—N3—C13—C12	−35.4 (2)
C3—C4—C10—C5	176.77 (14)	C12—C13—C14—C15	1.0 (2)
C3—C4—C10—C9	−1.2 (2)	N3—C13—C14—C15	−174.87 (13)
C6—C5—C10—C4	−177.25 (15)	C13—C14—C15—C16	1.1 (2)
C6—C5—C10—C9	0.6 (2)	C14—C15—C16—C17	−2.0 (2)
N1—C9—C10—C4	−0.4 (2)	C13—C12—C17—C16	1.2 (2)
C8—C9—C10—C4	177.72 (13)	C11—C12—C17—C16	−171.51 (14)
N1—C9—C10—C5	−178.44 (13)	C15—C16—C17—C12	0.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3ⁱ	0.95	2.55	3.209 (2)	127
C4—H4···O2ⁱⁱ	0.95	2.48	3.319 (2)	147
C17—H17···O1ⁱⁱⁱ	0.95	2.42	3.160 (2)	135

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₁N₃O₃
M_r	293.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	93
a, b, c (Å)	12.430 (3), 10.144 (3), 11.528 (3)
β (°)	116.449 (3)
V (Å³)	1301.4 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.50 × 0.40 × 0.15

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10410, 2949, 2679
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.145, 1.00
No. of reflections	2949
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.28

Computer programs: RAPID-AUTO (Rigaku, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3ⁱ	0.95	2.55	3.209 (2)	127
C4—H4···O2ⁱⁱ	0.95	2.48	3.319 (2)	147
C17—H17···O1ⁱⁱⁱ	0.95	2.42	3.160 (2)	135

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

Acknowledgements

The authors thank the Centre for Testing and Analysis, Cheng Du Branch, Chinese Academy of Sciences, for analytical support.

References

Oku, T., Kawai, Y., Satoh, S., Yamazaki, H., Kayakiri, N., Urano, Y., Yoshihara, K. & Yoshida, N. (1999). US Patent 6008230. Google Scholar
Oku, T., Sato, S., Inoue, T., Urano, Y., Yoshimitsu, T. & Yoshida, N. (1998). Jpn Patent 10 291 988. Google Scholar
Rigaku (2004). RAPID-AUTO. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar