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

In the title compound, C16H11NO4, the dihedral angle between the 10-membered coplanar chromone ring system and the benzene ring is 77.83 (3)°. In the crystal, weak C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network.

Related literature

For the preparation, see: Valkonen et al. (2012 ▶). For related structures, see: Sievänen et al. (2010 ▶); Gopaul et al. (2012 ▶); Valkonen et al. (2012 ▶). For general background to homoisoflavoinoids, see: Shaikh et al. (2011 ▶); du Toit et al. (2010 ▶).

Experimental

Crystal data

C16H11NO4

M = 281.26

Monoclinic,

a = 4.6082 (3) Å

b = 10.4219 (6) Å

c = 26.4468 (17) Å

β = 90.428 (1)°

V = 1270.10 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 173 K

0.42 × 0.22 × 0.04 mm

Data collection

Bruker Kappa DUO APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.956, T max = 0.996

16973 measured reflections

4246 independent reflections

3069 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.138

S = 1.04

4246 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.19 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 (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/S1600536813003589/ff2097sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813003589/ff2097Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813003589/ff2097Isup3.cml

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

C16H11NO4	F(000) = 584
Mr = 281.26	Dx = 1.471 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 4.6082 (3) Å	Cell parameters from 16973 reflections
b = 10.4219 (6) Å	θ = 1.5–31.6°
c = 26.4468 (17) Å	µ = 0.11 mm−1
β = 90.428 (1)°	T = 173 K
V = 1270.10 (14) Å3	Plate, colourless
Z = 4	0.42 × 0.22 × 0.04 mm

Bruker Kappa DUO APEXII diffractometer	4246 independent reflections
Radiation source: fine-focus sealed tube	3069 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
0.5° φ scans and ω scans	θmax = 31.6°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −3→6
Tmin = 0.956, Tmax = 0.996	k = −12→15
16973 measured reflections	l = −38→36

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0728P)2 + 0.2299P] where P = (Fo2 + 2Fc2)/3
4246 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.19 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	0.74839 (19)	0.65066 (9)	0.16340 (3)	0.0297 (2)
O2	0.12234 (19)	0.86867 (9)	0.23054 (3)	0.0307 (2)
O3	0.0611 (3)	0.69688 (13)	0.46889 (4)	0.0563 (4)
O4	0.2296 (3)	0.87629 (13)	0.49596 (4)	0.0569 (3)
N1	0.2075 (3)	0.79369 (12)	0.46362 (4)	0.0364 (3)
C1	0.6196 (2)	0.74864 (12)	0.13678 (4)	0.0254 (2)
C2	0.6533 (3)	0.62632 (12)	0.21073 (5)	0.0281 (2)
H2	0.7393	0.5562	0.2282	0.034*
C3	0.4471 (3)	0.69311 (11)	0.23514 (4)	0.0243 (2)
C4	0.3094 (2)	0.80163 (11)	0.21004 (4)	0.0229 (2)
C5	0.4068 (2)	0.82546 (11)	0.15828 (4)	0.0228 (2)
C6	0.2875 (3)	0.92474 (12)	0.12884 (5)	0.0304 (3)
H6	0.1413	0.9783	0.1426	0.037*
C7	0.3805 (3)	0.94494 (15)	0.08021 (5)	0.0380 (3)
H7	0.2999	1.0127	0.0606	0.046*
C8	0.5929 (3)	0.86601 (16)	0.05974 (5)	0.0392 (3)
H8	0.6559	0.8806	0.0261	0.047*
C9	0.7132 (3)	0.76728 (14)	0.08729 (5)	0.0343 (3)
H9	0.8565	0.7131	0.0730	0.041*
C10	0.3523 (3)	0.65438 (12)	0.28725 (5)	0.0303 (3)
H10A	0.4365	0.5691	0.2949	0.036*
H10B	0.1386	0.6446	0.2868	0.036*
C11	0.4334 (2)	0.74495 (11)	0.32985 (4)	0.0238 (2)
C12	0.2953 (3)	0.72947 (12)	0.37618 (4)	0.0265 (2)
H12	0.1554	0.6635	0.3805	0.032*
C13	0.3633 (3)	0.81075 (12)	0.41575 (4)	0.0261 (2)
C14	0.5657 (3)	0.90853 (12)	0.41192 (5)	0.0292 (3)
H14	0.6065	0.9640	0.4396	0.035*
C15	0.7057 (3)	0.92194 (12)	0.36619 (5)	0.0305 (3)
H15	0.8482	0.9871	0.3624	0.037*
C16	0.6411 (3)	0.84133 (12)	0.32557 (5)	0.0265 (2)
H16	0.7402	0.8523	0.2945	0.032*

	U11	U22	U33	U12	U13	U23
O1	0.0335 (4)	0.0285 (4)	0.0271 (4)	0.0059 (3)	0.0036 (3)	−0.0029 (3)
O2	0.0348 (5)	0.0295 (5)	0.0280 (5)	0.0034 (4)	0.0080 (3)	−0.0026 (4)
O3	0.0700 (8)	0.0657 (8)	0.0335 (6)	−0.0301 (6)	0.0160 (5)	−0.0001 (5)
O4	0.0765 (8)	0.0620 (8)	0.0325 (6)	−0.0123 (6)	0.0152 (5)	−0.0182 (5)
N1	0.0398 (6)	0.0462 (7)	0.0233 (5)	−0.0044 (5)	0.0039 (4)	−0.0002 (5)
C1	0.0279 (5)	0.0265 (5)	0.0218 (5)	−0.0018 (4)	0.0010 (4)	−0.0024 (4)
C2	0.0361 (6)	0.0226 (5)	0.0256 (6)	0.0018 (5)	−0.0035 (4)	−0.0009 (4)
C3	0.0329 (6)	0.0202 (5)	0.0198 (5)	−0.0043 (4)	−0.0007 (4)	−0.0008 (4)
C4	0.0267 (5)	0.0210 (5)	0.0212 (5)	−0.0042 (4)	0.0020 (4)	−0.0018 (4)
C5	0.0264 (5)	0.0227 (5)	0.0194 (5)	−0.0023 (4)	0.0010 (4)	−0.0003 (4)
C6	0.0347 (6)	0.0291 (6)	0.0275 (6)	0.0014 (5)	0.0007 (5)	0.0044 (5)
C7	0.0466 (8)	0.0399 (7)	0.0274 (7)	−0.0025 (6)	−0.0010 (5)	0.0105 (6)
C8	0.0419 (7)	0.0533 (9)	0.0224 (6)	−0.0078 (6)	0.0056 (5)	0.0041 (6)
C9	0.0349 (6)	0.0434 (7)	0.0247 (6)	−0.0021 (6)	0.0073 (5)	−0.0057 (5)
C10	0.0455 (7)	0.0238 (5)	0.0215 (6)	−0.0092 (5)	0.0003 (5)	0.0012 (4)
C11	0.0289 (5)	0.0220 (5)	0.0206 (5)	−0.0007 (4)	−0.0010 (4)	0.0018 (4)
C12	0.0298 (5)	0.0269 (5)	0.0230 (6)	−0.0058 (4)	0.0002 (4)	0.0028 (4)
C13	0.0296 (5)	0.0297 (6)	0.0191 (5)	0.0006 (4)	0.0012 (4)	0.0014 (4)
C14	0.0333 (6)	0.0275 (6)	0.0269 (6)	−0.0015 (5)	−0.0029 (5)	−0.0036 (5)
C15	0.0317 (6)	0.0286 (6)	0.0312 (6)	−0.0080 (5)	−0.0001 (5)	−0.0004 (5)
C16	0.0287 (5)	0.0265 (5)	0.0243 (6)	−0.0029 (4)	0.0021 (4)	0.0010 (4)

O1—C2	1.3533 (15)	C7—H7	0.9500
O1—C1	1.3727 (15)	C8—C9	1.375 (2)
O2—C4	1.2377 (14)	C8—H8	0.9500
O3—N1	1.2222 (17)	C9—H9	0.9500
O4—N1	1.2172 (16)	C10—C11	1.5145 (16)
N1—C13	1.4709 (16)	C10—H10A	0.9900
C1—C5	1.3905 (16)	C10—H10B	0.9900
C1—C9	1.3949 (17)	C11—C16	1.3926 (16)
C2—C3	1.3467 (17)	C11—C12	1.3942 (16)
C2—H2	0.9500	C12—C13	1.3804 (17)
C3—C4	1.4546 (16)	C12—H12	0.9500
C3—C10	1.5042 (16)	C13—C14	1.3858 (18)
C4—C5	1.4650 (15)	C14—C15	1.3823 (18)
C5—C6	1.4047 (17)	C14—H14	0.9500
C6—C7	1.3748 (18)	C15—C16	1.3941 (17)
C6—H6	0.9500	C15—H15	0.9500
C7—C8	1.391 (2)	C16—H16	0.9500
C2—O1—C1	118.16 (9)	C8—C9—C1	118.37 (12)
O4—N1—O3	123.17 (12)	C8—C9—H9	120.8
O4—N1—C13	118.71 (12)	C1—C9—H9	120.8
O3—N1—C13	118.12 (12)	C3—C10—C11	116.27 (10)
O1—C1—C5	121.47 (10)	C3—C10—H10A	108.2
O1—C1—C9	116.69 (11)	C11—C10—H10A	108.2
C5—C1—C9	121.83 (12)	C3—C10—H10B	108.2
C3—C2—O1	125.53 (11)	C11—C10—H10B	108.2
C3—C2—H2	117.2	H10A—C10—H10B	107.4
O1—C2—H2	117.2	C16—C11—C12	118.25 (11)
C2—C3—C4	119.35 (11)	C16—C11—C10	123.71 (11)
C2—C3—C10	120.76 (11)	C12—C11—C10	118.03 (10)
C4—C3—C10	119.87 (10)	C13—C12—C11	119.51 (11)
O2—C4—C3	122.81 (10)	C13—C12—H12	120.2
O2—C4—C5	122.20 (11)	C11—C12—H12	120.2
C3—C4—C5	114.98 (10)	C12—C13—C14	123.03 (11)
C1—C5—C6	118.15 (11)	C12—C13—N1	117.96 (11)
C1—C5—C4	120.43 (10)	C14—C13—N1	119.00 (11)
C6—C5—C4	121.42 (11)	C15—C14—C13	117.20 (11)
C7—C6—C5	120.52 (12)	C15—C14—H14	121.4
C7—C6—H6	119.7	C13—C14—H14	121.4
C5—C6—H6	119.7	C14—C15—C16	120.98 (11)
C6—C7—C8	119.91 (13)	C14—C15—H15	119.5
C6—C7—H7	120.0	C16—C15—H15	119.5
C8—C7—H7	120.0	C11—C16—C15	121.00 (11)
C9—C8—C7	121.22 (12)	C11—C16—H16	119.5
C9—C8—H8	119.4	C15—C16—H16	119.5
C7—C8—H8	119.4
C2—O1—C1—C5	3.07 (16)	C7—C8—C9—C1	−0.7 (2)
C2—O1—C1—C9	−177.07 (11)	O1—C1—C9—C8	−178.84 (12)
C1—O1—C2—C3	−2.33 (18)	C5—C1—C9—C8	1.02 (19)
O1—C2—C3—C4	−0.18 (19)	C2—C3—C10—C11	111.41 (14)
O1—C2—C3—C10	178.04 (11)	C4—C3—C10—C11	−70.37 (15)
C2—C3—C4—O2	−178.62 (11)	C3—C10—C11—C16	−15.66 (18)
C10—C3—C4—O2	3.14 (17)	C3—C10—C11—C12	165.39 (11)
C2—C3—C4—C5	1.83 (16)	C16—C11—C12—C13	1.26 (17)
C10—C3—C4—C5	−176.41 (10)	C10—C11—C12—C13	−179.73 (11)
O1—C1—C5—C6	179.30 (11)	C11—C12—C13—C14	−0.19 (19)
C9—C1—C5—C6	−0.55 (18)	C11—C12—C13—N1	178.39 (11)
O1—C1—C5—C4	−1.39 (17)	O4—N1—C13—C12	−168.33 (13)
C9—C1—C5—C4	178.76 (11)	O3—N1—C13—C12	11.53 (19)
O2—C4—C5—C1	179.38 (11)	O4—N1—C13—C14	10.31 (19)
C3—C4—C5—C1	−1.07 (15)	O3—N1—C13—C14	−169.83 (13)
O2—C4—C5—C6	−1.33 (18)	C12—C13—C14—C15	−0.96 (19)
C3—C4—C5—C6	178.22 (11)	N1—C13—C14—C15	−179.52 (12)
C1—C5—C6—C7	−0.23 (19)	C13—C14—C15—C16	1.02 (19)
C4—C5—C6—C7	−179.53 (12)	C12—C11—C16—C15	−1.20 (18)
C5—C6—C7—C8	0.5 (2)	C10—C11—C16—C15	179.86 (12)
C6—C7—C8—C9	0.0 (2)	C14—C15—C16—C11	0.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2	0.95	2.32	3.2663 (15)	171
C7—H7···O3i	0.95	2.65	3.5614 (19)	160
C8—H8···O3ii	0.95	2.54	3.3071 (18)	138
C14—H14···O4iii	0.95	2.50	3.4380 (17)	172
C15—H15···O1iv	0.95	2.62	3.5569 (15)	170
C16—H16···O2v	0.95	2.46	3.3764 (15)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2	0.95	2.32	3.2663 (15)	171
C7—H7⋯O3i	0.95	2.65	3.5614 (19)	160
C8—H8⋯O3ii	0.95	2.54	3.3071 (18)	138
C14—H14⋯O4iii	0.95	2.50	3.4380 (17)	172
C15—H15⋯O1iv	0.95	2.62	3.5569 (15)	170
C16—H16⋯O2v	0.95	2.46	3.3764 (15)	163

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