3-(4-Nitro-benz-yl)-4H-chromen-4-one.

In the title compound, C16H11NO4, the dihedral angle between the ten-membered chromen-4-one ring system (r.m.s. deviation = 0.0095 Å) and the benzene ring is 86.16 (5)°. In the crystal, mol-ecules are linked into a three-dimensional network by weak C-H⋯O hydrogen bonds. The crystal studied was a non-merohedral twin, with the minor twin component refining to 0.093 (1).

Related literature

For the preparation, see: Desideri et al. (2011 ▶); Valkonen et al. (2012 ▶). For related structures, see: Valkonen et al. (2012 ▶); Gopaul et al. (2013 ▶). For the biological activity of homoisoflavonoids, see: Abegaz et al. (2007 ▶).

Experimental

Crystal data

C16H11NO4

M = 281.26

Monoclinic,

a = 4.9246 (9) Å

b = 10.0160 (19) Å

c = 25.907 (5) Å

β = 92.845 (4)°

V = 1276.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 173 K

0.35 × 0.09 × 0.08 mm

Data collection

Bruker Kappa DUO APEXII diffractometer

Absorption correction: multi-scan (TWINABS; Sheldrick, 1997 ▶) T min = 0.964, T max = 0.992

87638 measured reflections

3303 independent reflections

2887 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.154

S = 1.09

3303 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813006119/fj2618sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813006119/fj2618Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813006119/fj2618Isup3.cml

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

C16H11NO4	F(000) = 584
Mr = 281.26	Dx = 1.464 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3303 reflections
a = 4.9246 (9) Å	θ = 1.6–27.4°
b = 10.0160 (19) Å	µ = 0.11 mm−1
c = 25.907 (5) Å	T = 173 K
β = 92.845 (4)°	Needle, colourless
V = 1276.3 (4) Å3	0.35 × 0.09 × 0.08 mm
Z = 4

Bruker Kappa DUO APEXII diffractometer	3303 independent reflections
Radiation source: fine-focus sealed tube	2887 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.063
0.5° φ scans and ω scans	θmax = 27.4°, θmin = 1.6°
Absorption correction: multi-scan (TWINABS; Sheldrick, 1997)	h = −6→6
Tmin = 0.964, Tmax = 0.992	k = 0→12
87638 measured reflections	l = 0→33

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0779P)2 + 0.7278P] where P = (Fo2 + 2Fc2)/3
3303 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.23 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	0.9485 (3)	0.30392 (15)	0.16095 (6)	0.0339 (4)
O2	0.3498 (3)	0.50967 (15)	0.23136 (6)	0.0355 (4)
O3	0.8175 (4)	0.63590 (18)	0.49727 (6)	0.0449 (4)
O4	1.1513 (4)	0.7098 (2)	0.45470 (7)	0.0522 (5)
N1	0.9499 (4)	0.63878 (18)	0.45839 (7)	0.0328 (4)
C1	0.8059 (4)	0.4022 (2)	0.13399 (8)	0.0282 (4)
C2	0.8774 (5)	0.2756 (2)	0.20963 (8)	0.0323 (4)
H2	0.9747	0.2063	0.2275	0.039*
C3	0.6800 (4)	0.33749 (19)	0.23490 (7)	0.0281 (4)
C4	0.5276 (4)	0.44552 (19)	0.20968 (7)	0.0264 (4)
C5	0.5991 (4)	0.47384 (19)	0.15623 (7)	0.0260 (4)
C6	0.4653 (5)	0.5734 (2)	0.12658 (8)	0.0333 (5)
H6	0.3235	0.6233	0.1410	0.040*
C7	0.5368 (5)	0.6000 (2)	0.07681 (9)	0.0383 (5)
H7	0.4457	0.6681	0.0572	0.046*
C8	0.7441 (5)	0.5262 (3)	0.05552 (8)	0.0402 (5)
H8	0.7927	0.5445	0.0212	0.048*
C9	0.8801 (5)	0.4268 (2)	0.08354 (8)	0.0364 (5)
H9	1.0205	0.3767	0.0688	0.044*
C10	0.6125 (5)	0.2953 (2)	0.28877 (8)	0.0343 (5)
H10A	0.6971	0.2072	0.2960	0.041*
H10B	0.4131	0.2836	0.2895	0.041*
C11	0.7026 (4)	0.39038 (19)	0.33199 (7)	0.0273 (4)
C12	0.5763 (5)	0.3825 (2)	0.37937 (8)	0.0347 (5)
H12	0.4330	0.3203	0.3831	0.042*
C13	0.6553 (5)	0.4630 (2)	0.42049 (8)	0.0341 (5)
H13	0.5682	0.4569	0.4523	0.041*
C14	0.8652 (4)	0.55301 (19)	0.41435 (7)	0.0273 (4)
C15	0.9971 (4)	0.5640 (2)	0.36858 (8)	0.0313 (4)
H15	1.1411	0.6261	0.3653	0.038*
C16	0.9136 (4)	0.4816 (2)	0.32739 (8)	0.0309 (4)
H16	1.0018	0.4879	0.2957	0.037*

	U11	U22	U33	U12	U13	U23
O1	0.0369 (8)	0.0348 (7)	0.0303 (7)	0.0077 (7)	0.0045 (6)	−0.0026 (6)
O2	0.0400 (8)	0.0371 (8)	0.0303 (8)	0.0037 (7)	0.0105 (6)	−0.0019 (6)
O3	0.0529 (10)	0.0535 (10)	0.0290 (8)	−0.0090 (8)	0.0089 (7)	−0.0110 (7)
O4	0.0546 (11)	0.0583 (11)	0.0440 (10)	−0.0286 (9)	0.0047 (8)	−0.0118 (8)
N1	0.0365 (9)	0.0334 (9)	0.0284 (9)	−0.0030 (8)	0.0001 (7)	−0.0015 (7)
C1	0.0308 (9)	0.0287 (9)	0.0250 (9)	−0.0015 (8)	0.0003 (8)	−0.0025 (7)
C2	0.0409 (11)	0.0274 (9)	0.0282 (10)	0.0017 (9)	−0.0023 (9)	−0.0006 (8)
C3	0.0368 (10)	0.0251 (9)	0.0222 (9)	−0.0056 (8)	0.0003 (8)	−0.0022 (7)
C4	0.0315 (9)	0.0242 (8)	0.0237 (9)	−0.0051 (8)	0.0034 (8)	−0.0030 (7)
C5	0.0282 (9)	0.0256 (9)	0.0243 (9)	−0.0035 (7)	0.0019 (8)	−0.0025 (7)
C6	0.0362 (10)	0.0321 (10)	0.0316 (10)	0.0035 (9)	0.0018 (9)	0.0024 (8)
C7	0.0425 (12)	0.0404 (11)	0.0318 (11)	0.0005 (10)	−0.0014 (9)	0.0089 (9)
C8	0.0433 (12)	0.0524 (13)	0.0251 (10)	−0.0064 (11)	0.0037 (9)	0.0058 (9)
C9	0.0358 (11)	0.0461 (12)	0.0278 (10)	−0.0012 (10)	0.0067 (9)	−0.0044 (9)
C10	0.0513 (13)	0.0276 (9)	0.0239 (10)	−0.0063 (9)	0.0009 (9)	0.0014 (8)
C11	0.0334 (10)	0.0260 (9)	0.0222 (9)	0.0002 (8)	−0.0005 (8)	0.0026 (7)
C12	0.0384 (11)	0.0375 (11)	0.0286 (10)	−0.0126 (9)	0.0042 (9)	0.0005 (8)
C13	0.0365 (11)	0.0414 (11)	0.0249 (9)	−0.0062 (9)	0.0065 (9)	−0.0004 (8)
C14	0.0290 (9)	0.0290 (9)	0.0238 (9)	0.0007 (8)	−0.0001 (7)	−0.0001 (7)
C15	0.0320 (10)	0.0334 (10)	0.0285 (10)	−0.0060 (8)	0.0017 (8)	0.0022 (8)
C16	0.0337 (10)	0.0340 (10)	0.0253 (9)	−0.0029 (9)	0.0054 (8)	0.0017 (8)

O1—C2	1.356 (3)	C7—H7	0.9500
O1—C1	1.379 (3)	C8—C9	1.385 (3)
O2—C4	1.243 (2)	C8—H8	0.9500
O3—N1	1.227 (2)	C9—H9	0.9500
O4—N1	1.228 (2)	C10—C11	1.519 (3)
N1—C14	1.472 (3)	C10—H10A	0.9900
C1—C5	1.394 (3)	C10—H10B	0.9900
C1—C9	1.397 (3)	C11—C16	1.393 (3)
C2—C3	1.350 (3)	C11—C12	1.406 (3)
C2—H2	0.9500	C12—C13	1.376 (3)
C3—C4	1.453 (3)	C12—H12	0.9500
C3—C10	1.511 (3)	C13—C14	1.387 (3)
C4—C5	1.473 (3)	C13—H13	0.9500
C5—C6	1.403 (3)	C14—C15	1.385 (3)
C6—C7	1.379 (3)	C15—C16	1.394 (3)
C6—H6	0.9500	C15—H15	0.9500
C7—C8	1.396 (3)	C16—H16	0.9500
C2—O1—C1	118.18 (16)	C8—C9—C1	118.4 (2)
O3—N1—O4	122.80 (18)	C8—C9—H9	120.8
O3—N1—C14	118.74 (17)	C1—C9—H9	120.8
O4—N1—C14	118.46 (18)	C3—C10—C11	115.84 (17)
O1—C1—C5	121.51 (18)	C3—C10—H10A	108.3
O1—C1—C9	116.75 (18)	C11—C10—H10A	108.3
C5—C1—C9	121.74 (19)	C3—C10—H10B	108.3
C3—C2—O1	125.48 (19)	C11—C10—H10B	108.3
C3—C2—H2	117.3	H10A—C10—H10B	107.4
O1—C2—H2	117.3	C16—C11—C12	118.41 (18)
C2—C3—C4	119.50 (18)	C16—C11—C10	122.68 (18)
C2—C3—C10	121.08 (19)	C12—C11—C10	118.86 (18)
C4—C3—C10	119.42 (18)	C13—C12—C11	121.51 (19)
O2—C4—C3	122.79 (18)	C13—C12—H12	119.2
O2—C4—C5	122.13 (18)	C11—C12—H12	119.2
C3—C4—C5	115.08 (17)	C12—C13—C14	118.41 (18)
C1—C5—C6	118.21 (18)	C12—C13—H13	120.8
C1—C5—C4	120.18 (18)	C14—C13—H13	120.8
C6—C5—C4	121.60 (18)	C15—C14—C13	122.27 (19)
C7—C6—C5	121.0 (2)	C15—C14—N1	119.37 (18)
C7—C6—H6	119.5	C13—C14—N1	118.35 (17)
C5—C6—H6	119.5	C14—C15—C16	118.37 (19)
C6—C7—C8	119.5 (2)	C14—C15—H15	120.8
C6—C7—H7	120.2	C16—C15—H15	120.8
C8—C7—H7	120.2	C11—C16—C15	121.03 (18)
C9—C8—C7	121.2 (2)	C11—C16—H16	119.5
C9—C8—H8	119.4	C15—C16—H16	119.5
C7—C8—H8	119.4
C2—O1—C1—C5	1.8 (3)	C7—C8—C9—C1	−0.3 (4)
C2—O1—C1—C9	−178.58 (19)	O1—C1—C9—C8	−179.1 (2)
C1—O1—C2—C3	−1.4 (3)	C5—C1—C9—C8	0.5 (3)
O1—C2—C3—C4	−0.9 (3)	C2—C3—C10—C11	107.3 (2)
O1—C2—C3—C10	178.39 (19)	C4—C3—C10—C11	−73.4 (3)
C2—C3—C4—O2	−177.5 (2)	C3—C10—C11—C16	−23.1 (3)
C10—C3—C4—O2	3.2 (3)	C3—C10—C11—C12	159.7 (2)
C2—C3—C4—C5	2.6 (3)	C16—C11—C12—C13	0.4 (3)
C10—C3—C4—C5	−176.76 (17)	C10—C11—C12—C13	177.8 (2)
O1—C1—C5—C6	179.24 (18)	C11—C12—C13—C14	−0.1 (3)
C9—C1—C5—C6	−0.3 (3)	C12—C13—C14—C15	−0.3 (3)
O1—C1—C5—C4	−0.1 (3)	C12—C13—C14—N1	−179.9 (2)
C9—C1—C5—C4	−179.63 (19)	O3—N1—C14—C15	174.2 (2)
O2—C4—C5—C1	177.96 (19)	O4—N1—C14—C15	−6.2 (3)
C3—C4—C5—C1	−2.1 (3)	O3—N1—C14—C13	−6.2 (3)
O2—C4—C5—C6	−1.3 (3)	O4—N1—C14—C13	173.4 (2)
C3—C4—C5—C6	178.63 (18)	C13—C14—C15—C16	0.4 (3)
C1—C5—C6—C7	−0.1 (3)	N1—C14—C15—C16	179.96 (19)
C4—C5—C6—C7	179.1 (2)	C12—C11—C16—C15	−0.3 (3)
C5—C6—C7—C8	0.4 (3)	C10—C11—C16—C15	−177.6 (2)
C6—C7—C8—C9	−0.2 (4)	C14—C15—C16—C11	0.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2i	0.95	2.38	3.322 (3)	170
C7—H7···O3ii	0.95	2.56	3.491 (3)	166
C9—H9···O4iii	0.95	2.42	3.355 (3)	167
C13—H13···O3iv	0.95	2.53	3.382 (3)	149
C16—H16···O2v	0.95	2.46	3.378 (3)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2i	0.95	2.38	3.322 (3)	170
C7—H7⋯O3ii	0.95	2.56	3.491 (3)	166
C9—H9⋯O4iii	0.95	2.42	3.355 (3)	167
C13—H13⋯O3iv	0.95	2.53	3.382 (3)	149
C16—H16⋯O2v	0.95	2.46	3.378 (3)	163

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