4-Nitro-N-(8-quinol-yl)benzamide.

In the title compound, C(16)H(11)N(3)O(3), the amide group is twisted away from the plane of the quinoline benzene ring by 3.93 (5)°, but is twisted away from the nitro-benzene ring by 22.68 (4)°. A weak intra-molecular C-H⋯O hydrogen bond is observed. In the crystal structure, mol-ecules are linked into a chain along the a axis by inter-molecular C-H⋯O hydrogen bonds.

Related literature

For general background, see: Daoud et al. (2000 ▶); Westaway et al. (2006 ▶). For related structures, see: Lei et al. (2008a ▶,b ▶).

Experimental

Crystal data

C16H11N3O3

M = 293.28

Monoclinic,

a = 7.5230 (15) Å

b = 25.031 (5) Å

c = 6.9596 (15) Å

β = 100.081 (3)°

V = 1290.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 93 (2) K

0.43 × 0.30 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: none

10531 measured reflections

2905 independent reflections

2542 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.135

S = 1.00

2905 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.27 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038038/ci2725sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038038/ci2725Isup2.hkl

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

C16H11N3O3	F000 = 608
Mr = 293.28	Dx = 1.510 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3970 reflections
a = 7.5230 (15) Å	θ = 3.1–27.5º
b = 25.031 (5) Å	µ = 0.11 mm−1
c = 6.9596 (15) Å	T = 93 (2) K
β = 100.081 (3)º	Block, white
V = 1290.3 (5) Å3	0.43 × 0.30 × 0.15 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	2542 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Monochromator: graphite	θmax = 27.5º
T = 93(2) K	θmin = 3.1º
ω scans	h = −9→9
Absorption correction: none	k = −32→21
10531 measured reflections	l = −9→9
2905 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046	H-atom parameters constrained
wR(F2) = 0.135	w = 1/[σ2(Fo2) + (0.0868P)2 + 0.086P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
2905 reflections	Δρmax = 0.27 e Å−3
199 parameters	Δρmin = −0.27 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.69786 (14)	0.38934 (4)	0.50464 (16)	0.0233 (3)
O2	−0.00273 (15)	0.55640 (4)	0.15111 (17)	0.0268 (3)
O3	−0.19660 (14)	0.49876 (4)	0.22148 (16)	0.0286 (3)
N1	0.38108 (16)	0.21834 (5)	0.42312 (18)	0.0192 (3)
N2	0.51347 (16)	0.31652 (5)	0.46574 (18)	0.0188 (3)
H2N	0.3993	0.3069	0.4397	0.023*
N3	−0.04073 (16)	0.51288 (5)	0.21646 (18)	0.0202 (3)
C2	0.3131 (2)	0.16969 (6)	0.3996 (2)	0.0220 (3)
H2	0.1860	0.1663	0.3619	0.026*
C3	0.4163 (2)	0.12257 (6)	0.4267 (2)	0.0225 (3)
H3	0.3600	0.0886	0.4073	0.027*
C4	0.5990 (2)	0.12671 (6)	0.4816 (2)	0.0212 (3)
H4	0.6713	0.0954	0.5017	0.025*
C5	0.8683 (2)	0.18552 (6)	0.5631 (2)	0.0208 (3)
H5	0.9473	0.1556	0.5820	0.025*
C6	0.9366 (2)	0.23613 (6)	0.5891 (2)	0.0212 (3)
H6	1.0631	0.2410	0.6273	0.025*
C7	0.8229 (2)	0.28130 (6)	0.5603 (2)	0.0199 (3)
H7	0.8729	0.3161	0.5803	0.024*
C8	0.64030 (19)	0.27499 (5)	0.5036 (2)	0.0170 (3)
C9	0.56440 (19)	0.22250 (5)	0.4778 (2)	0.0172 (3)
C10	0.6807 (2)	0.17763 (6)	0.5084 (2)	0.0187 (3)
C11	0.54650 (19)	0.36987 (6)	0.4646 (2)	0.0183 (3)
C12	0.38470 (19)	0.40539 (5)	0.4061 (2)	0.0176 (3)
C13	0.2074 (2)	0.39106 (6)	0.4189 (2)	0.0192 (3)
H13	0.1833	0.3569	0.4679	0.023*
C14	0.06669 (19)	0.42655 (6)	0.3603 (2)	0.0196 (3)
H14	−0.0540	0.4174	0.3698	0.023*
C15	0.10717 (18)	0.47577 (6)	0.2876 (2)	0.0177 (3)
C16	0.2814 (2)	0.49139 (6)	0.2769 (2)	0.0197 (3)
H16	0.3051	0.5258	0.2295	0.024*
C17	0.4202 (2)	0.45575 (6)	0.3369 (2)	0.0194 (3)
H17	0.5410	0.4657	0.3308	0.023*

	U11	U22	U33	U12	U13	U23
O1	0.0184 (5)	0.0193 (5)	0.0318 (6)	−0.0021 (4)	0.0033 (5)	0.0004 (4)
O2	0.0276 (6)	0.0197 (6)	0.0326 (6)	0.0013 (4)	0.0041 (5)	0.0062 (5)
O3	0.0170 (6)	0.0307 (6)	0.0390 (7)	0.0022 (4)	0.0079 (5)	0.0071 (5)
N1	0.0178 (6)	0.0208 (6)	0.0201 (6)	−0.0022 (5)	0.0061 (5)	−0.0010 (5)
N2	0.0153 (6)	0.0159 (6)	0.0255 (7)	0.0000 (4)	0.0045 (5)	−0.0006 (5)
N3	0.0199 (6)	0.0209 (6)	0.0202 (6)	0.0015 (5)	0.0049 (5)	−0.0005 (5)
C2	0.0219 (8)	0.0245 (8)	0.0201 (8)	−0.0037 (6)	0.0055 (6)	−0.0010 (6)
C3	0.0285 (8)	0.0194 (7)	0.0201 (7)	−0.0043 (6)	0.0055 (6)	−0.0016 (6)
C4	0.0275 (8)	0.0183 (7)	0.0190 (7)	0.0024 (6)	0.0073 (6)	0.0004 (6)
C5	0.0205 (7)	0.0221 (7)	0.0198 (7)	0.0055 (6)	0.0037 (6)	0.0022 (6)
C6	0.0181 (7)	0.0252 (8)	0.0207 (7)	0.0023 (6)	0.0044 (6)	0.0013 (6)
C7	0.0213 (7)	0.0194 (7)	0.0198 (7)	−0.0020 (6)	0.0053 (6)	−0.0009 (6)
C8	0.0180 (7)	0.0183 (7)	0.0157 (7)	0.0022 (5)	0.0056 (6)	0.0001 (5)
C9	0.0179 (7)	0.0195 (7)	0.0150 (7)	0.0011 (5)	0.0051 (6)	−0.0004 (5)
C10	0.0224 (7)	0.0201 (7)	0.0144 (7)	0.0011 (6)	0.0054 (6)	0.0007 (5)
C11	0.0194 (7)	0.0186 (7)	0.0173 (7)	−0.0009 (6)	0.0047 (6)	−0.0011 (5)
C12	0.0180 (7)	0.0174 (7)	0.0173 (7)	−0.0012 (5)	0.0033 (6)	−0.0022 (5)
C13	0.0215 (7)	0.0173 (7)	0.0192 (7)	−0.0011 (6)	0.0041 (6)	−0.0005 (6)
C14	0.0183 (7)	0.0197 (7)	0.0214 (7)	−0.0013 (6)	0.0055 (6)	−0.0013 (6)
C15	0.0183 (7)	0.0174 (7)	0.0171 (7)	0.0025 (5)	0.0022 (6)	−0.0010 (5)
C16	0.0224 (8)	0.0173 (7)	0.0196 (7)	−0.0032 (6)	0.0046 (6)	0.0004 (6)
C17	0.0190 (7)	0.0188 (7)	0.0210 (7)	−0.0024 (6)	0.0047 (6)	−0.0012 (6)

O1—C11	1.2250 (17)	C6—C7	1.411 (2)
O2—N3	1.2332 (15)	C6—H6	0.95
O3—N3	1.2311 (16)	C7—C8	1.370 (2)
N1—C2	1.3198 (18)	C7—H7	0.95
N1—C9	1.3689 (18)	C8—C9	1.4311 (19)
N2—C11	1.3587 (18)	C9—C10	1.4166 (19)
N2—C8	1.4045 (17)	C11—C12	1.505 (2)
N2—H2N	0.88	C12—C17	1.3921 (19)
N3—C15	1.4673 (18)	C12—C13	1.399 (2)
C2—C3	1.406 (2)	C13—C14	1.388 (2)
C2—H2	0.95	C13—H13	0.95
C3—C4	1.365 (2)	C14—C15	1.386 (2)
C3—H3	0.95	C14—H14	0.95
C4—C10	1.413 (2)	C15—C16	1.382 (2)
C4—H4	0.95	C16—C17	1.381 (2)
C5—C6	1.367 (2)	C16—H16	0.95
C5—C10	1.410 (2)	C17—H17	0.95
C5—H5	0.95
C2—N1—C9	117.02 (12)	N1—C9—C10	123.15 (13)
C11—N2—C8	127.57 (12)	N1—C9—C8	117.72 (12)
C11—N2—H2N	116.2	C10—C9—C8	119.12 (13)
C8—N2—H2N	116.2	C5—C10—C4	123.60 (13)
O3—N3—O2	123.20 (12)	C5—C10—C9	119.48 (13)
O3—N3—C15	118.58 (12)	C4—C10—C9	116.93 (14)
O2—N3—C15	118.20 (12)	O1—C11—N2	123.60 (14)
N1—C2—C3	124.36 (14)	O1—C11—C12	120.14 (13)
N1—C2—H2	117.8	N2—C11—C12	116.24 (12)
C3—C2—H2	117.8	C17—C12—C13	119.82 (13)
C4—C3—C2	118.62 (14)	C17—C12—C11	115.68 (13)
C4—C3—H3	120.7	C13—C12—C11	124.50 (13)
C2—C3—H3	120.7	C14—C13—C12	120.28 (13)
C3—C4—C10	119.91 (14)	C14—C13—H13	119.9
C3—C4—H4	120.0	C12—C13—H13	119.9
C10—C4—H4	120.0	C15—C14—C13	118.12 (13)
C6—C5—C10	120.06 (13)	C15—C14—H14	120.9
C6—C5—H5	120.0	C13—C14—H14	120.9
C10—C5—H5	120.0	C16—C15—C14	122.82 (13)
C5—C6—C7	121.27 (14)	C16—C15—N3	118.23 (13)
C5—C6—H6	119.4	C14—C15—N3	118.94 (12)
C7—C6—H6	119.4	C17—C16—C15	118.37 (13)
C8—C7—C6	120.06 (13)	C17—C16—H16	120.8
C8—C7—H7	120.0	C15—C16—H16	120.8
C6—C7—H7	120.0	C16—C17—C12	120.56 (13)
C7—C8—N2	125.63 (13)	C16—C17—H17	119.7
C7—C8—C9	119.99 (12)	C12—C17—H17	119.7
N2—C8—C9	114.38 (12)
C9—N1—C2—C3	−0.1 (2)	C8—C9—C10—C4	179.81 (12)
N1—C2—C3—C4	0.2 (2)	C8—N2—C11—O1	−2.6 (2)
C2—C3—C4—C10	−0.5 (2)	C8—N2—C11—C12	176.13 (12)
C10—C5—C6—C7	−0.6 (2)	O1—C11—C12—C17	21.26 (19)
C5—C6—C7—C8	−0.6 (2)	N2—C11—C12—C17	−157.50 (13)
C6—C7—C8—N2	−178.40 (13)	O1—C11—C12—C13	−158.21 (14)
C6—C7—C8—C9	1.4 (2)	N2—C11—C12—C13	23.0 (2)
C11—N2—C8—C7	4.8 (2)	C17—C12—C13—C14	0.9 (2)
C11—N2—C8—C9	−174.98 (13)	C11—C12—C13—C14	−179.67 (13)
C2—N1—C9—C10	0.3 (2)	C12—C13—C14—C15	0.7 (2)
C2—N1—C9—C8	179.93 (12)	C13—C14—C15—C16	−2.1 (2)
C7—C8—C9—N1	179.29 (12)	C13—C14—C15—N3	177.21 (12)
N2—C8—C9—N1	−0.91 (19)	O3—N3—C15—C16	178.40 (13)
C7—C8—C9—C10	−1.0 (2)	O2—N3—C15—C16	−0.28 (19)
N2—C8—C9—C10	178.77 (12)	O3—N3—C15—C14	−0.90 (19)
C6—C5—C10—C4	−178.98 (13)	O2—N3—C15—C14	−179.58 (13)
C6—C5—C10—C9	1.0 (2)	C14—C15—C16—C17	1.7 (2)
C3—C4—C10—C5	−179.42 (13)	N3—C15—C16—C17	−177.59 (12)
C3—C4—C10—C9	0.6 (2)	C15—C16—C17—C12	0.0 (2)
N1—C9—C10—C5	179.52 (12)	C13—C12—C17—C16	−1.3 (2)
C8—C9—C10—C5	−0.1 (2)	C11—C12—C17—C16	179.23 (12)
N1—C9—C10—C4	−0.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1	0.95	2.26	2.8672 (19)	121
C14—H14···O1i	0.95	2.34	3.2483 (18)	160
C17—H17···O3ii	0.95	2.38	3.3050 (18)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1	0.95	2.26	2.8672 (19)	121
C14—H14⋯O1i	0.95	2.34	3.2483 (18)	160
C17—H17⋯O3ii	0.95	2.38	3.3050 (18)	163

Symmetry codes: (i) ; (ii) .