4-Hydr-oxy-3-meth-oxy-5-nitro-aceto-phenone (5-nitro-apocynin).

The title mol-ecule, C(9)H(9)NO(5), is close to planar (r.m.s. deviation from the mean plane of the non-H atoms = 0.058 Å). The OH group forms a bifurcated O-H⋯(O,O) hydrogen bond, with the intra-molecular component to a nitro O atom and the inter-molecular component to a keto O atom, the latter resulting in chains along [20]. A C-H⋯O inter-action reinforces the packing.

Related literature

For medicinal background, see: Gernapudi et al. (2009 ▶); Geronikaki & Gavalas (2006 ▶); Hayashi et al. (2005 ▶); Heumuller et al. (2008 ▶); Matés et al. (2009 ▶); Muijsers et al. (2001 ▶); Sawa et al. (2000 ▶); Schopfer et al. (2003 ▶); Stefanska & Pawliczak (2008 ▶); Stolk et al. (1994 ▶); Tajik et al. (2009 ▶); Thomas et al. (2002 ▶); Touyz (2008 ▶); Ximenes et al. (2007 ▶).

Experimental

Crystal data

C9H9NO5

M = 211.17

Monoclinic,

a = 6.6598 (10) Å

b = 16.815 (2) Å

c = 8.0491 (11) Å

β = 96.485 (7)°

V = 895.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 90 K

0.40 × 0.30 × 0.15 mm

Data collection

Nonius KappaCCD diffractometer with Oxford Cryostream

Absorption correction: none

22479 measured reflections

4255 independent reflections

3226 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.120

S = 1.04

4255 reflections

147 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.62 e Å−3

Δρmin = −0.32 e Å−3

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680903390X/hb5058sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903390X/hb5058Isup2.hkl

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

C9H9NO5	F(000) = 440
Mr = 211.17	Dx = 1.566 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4183 reflections
a = 6.6598 (10) Å	θ = 2.5–36.3°
b = 16.815 (2) Å	µ = 0.13 mm−1
c = 8.0491 (11) Å	T = 90 K
β = 96.485 (7)°	Needle fragment, golden yellow
V = 895.6 (2) Å3	0.40 × 0.30 × 0.15 mm
Z = 4

Nonius KappaCCD diffractometer with Oxford Cryostream	3226 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
graphite	θmax = 36.3°, θmin = 2.8°
ω and φ scans	h = −10→10
22479 measured reflections	k = −28→26
4255 independent reflections	l = −13→13

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0585P)2 + 0.2019P] where P = (Fo2 + 2Fc2)/3
4255 reflections	(Δ/σ)max < 0.001
147 parameters	Δρmax = 0.62 e Å−3
0 restraints	Δρmin = −0.32 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	0.70859 (9)	0.17341 (4)	0.57565 (8)	0.01682 (13)
H1O	0.805 (2)	0.1965 (9)	0.5277 (18)	0.025*
O2	0.40131 (9)	0.12263 (4)	0.70993 (9)	0.01727 (13)
O3	0.03482 (9)	0.36827 (4)	0.88871 (9)	0.01850 (14)
O4	0.90549 (10)	0.29612 (4)	0.48481 (9)	0.02148 (15)
O5	0.81333 (10)	0.41618 (4)	0.53665 (9)	0.02082 (14)
N1	0.79036 (11)	0.34401 (4)	0.54412 (9)	0.01483 (13)
C1	0.32973 (11)	0.33924 (5)	0.76315 (10)	0.01274 (14)
C2	0.29375 (12)	0.25663 (5)	0.77082 (10)	0.01340 (14)
H2	0.1831 (18)	0.2368 (8)	0.8237 (15)	0.016*
C3	0.42194 (12)	0.20294 (5)	0.70775 (10)	0.01312 (14)
C4	0.59325 (12)	0.22979 (5)	0.63245 (10)	0.01309 (14)
C5	0.62316 (11)	0.31230 (5)	0.62424 (10)	0.01315 (14)
C6	0.49407 (12)	0.36689 (5)	0.68977 (10)	0.01365 (14)
H6	0.5227 (18)	0.4219 (8)	0.6815 (15)	0.016*
C7	0.22582 (13)	0.09248 (5)	0.77728 (12)	0.01791 (16)
H7A	0.2325	0.1066	0.8959	0.027*
H7B	0.2211	0.0345	0.7654	0.027*
H7C	0.1041	0.1158	0.7165	0.027*
C8	0.18762 (12)	0.39440 (5)	0.83692 (10)	0.01404 (14)
C9	0.23465 (14)	0.48181 (5)	0.84358 (12)	0.01944 (17)
H9A	0.2105	0.5043	0.7308	0.029*
H9B	0.3766	0.4897	0.8876	0.029*
H9C	0.1476	0.5084	0.9167	0.029*

	U11	U22	U33	U12	U13	U23
O1	0.0147 (3)	0.0152 (3)	0.0220 (3)	0.0018 (2)	0.0084 (2)	−0.0013 (2)
O2	0.0163 (3)	0.0115 (3)	0.0255 (3)	−0.0003 (2)	0.0087 (2)	0.0008 (2)
O3	0.0156 (3)	0.0183 (3)	0.0233 (3)	−0.0003 (2)	0.0094 (2)	−0.0002 (2)
O4	0.0179 (3)	0.0203 (3)	0.0287 (3)	−0.0003 (2)	0.0136 (3)	−0.0035 (3)
O5	0.0232 (3)	0.0155 (3)	0.0257 (3)	−0.0043 (2)	0.0110 (3)	0.0008 (2)
N1	0.0137 (3)	0.0163 (3)	0.0152 (3)	−0.0018 (2)	0.0047 (2)	−0.0004 (2)
C1	0.0120 (3)	0.0131 (3)	0.0137 (3)	0.0005 (2)	0.0036 (2)	0.0006 (2)
C2	0.0123 (3)	0.0135 (3)	0.0150 (3)	−0.0002 (2)	0.0042 (2)	0.0007 (3)
C3	0.0124 (3)	0.0126 (3)	0.0148 (3)	−0.0004 (2)	0.0033 (2)	0.0009 (3)
C4	0.0118 (3)	0.0144 (3)	0.0135 (3)	0.0008 (2)	0.0033 (2)	−0.0004 (3)
C5	0.0111 (3)	0.0152 (3)	0.0139 (3)	−0.0015 (2)	0.0044 (2)	0.0002 (3)
C6	0.0133 (3)	0.0135 (3)	0.0147 (3)	−0.0003 (2)	0.0038 (2)	0.0005 (3)
C7	0.0172 (3)	0.0152 (3)	0.0223 (4)	−0.0020 (3)	0.0065 (3)	0.0023 (3)
C8	0.0136 (3)	0.0146 (3)	0.0145 (3)	0.0013 (2)	0.0039 (3)	0.0012 (3)
C9	0.0201 (4)	0.0134 (3)	0.0264 (4)	0.0013 (3)	0.0095 (3)	0.0010 (3)

O1—C4	1.3330 (10)	C2—H2	0.952 (12)
O1—H1O	0.878 (14)	C3—C4	1.4245 (11)
O2—C3	1.3576 (10)	C4—C5	1.4043 (12)
O2—C7	1.4352 (11)	C5—C6	1.4008 (11)
O3—C8	1.2240 (10)	C6—H6	0.948 (13)
O4—N1	1.2438 (10)	C7—H7A	0.9800
O5—N1	1.2255 (10)	C7—H7B	0.9800
N1—C5	1.4499 (10)	C7—H7C	0.9800
C1—C6	1.3817 (11)	C8—C9	1.5026 (12)
C1—C2	1.4120 (12)	C9—H9A	0.9800
C1—C8	1.4952 (11)	C9—H9B	0.9800
C2—C3	1.3783 (11)	C9—H9C	0.9800
C4—O1—H1O	108.5 (10)	C4—C5—N1	120.29 (7)
C3—O2—C7	116.37 (7)	C1—C6—C5	119.34 (8)
O5—N1—O4	122.44 (7)	C1—C6—H6	122.2 (7)
O5—N1—C5	119.50 (7)	C5—C6—H6	118.4 (7)
O4—N1—C5	118.06 (7)	O2—C7—H7A	109.5
C6—C1—C2	119.75 (7)	O2—C7—H7B	109.5
C6—C1—C8	121.91 (7)	H7A—C7—H7B	109.5
C2—C1—C8	118.34 (7)	O2—C7—H7C	109.5
C3—C2—C1	120.87 (7)	H7A—C7—H7C	109.5
C3—C2—H2	118.5 (8)	H7B—C7—H7C	109.5
C1—C2—H2	120.6 (8)	O3—C8—C1	120.03 (8)
O2—C3—C2	125.38 (7)	O3—C8—C9	121.13 (8)
O2—C3—C4	114.07 (7)	C1—C8—C9	118.83 (7)
C2—C3—C4	120.55 (7)	C8—C9—H9A	109.5
O1—C4—C5	126.60 (7)	C8—C9—H9B	109.5
O1—C4—C3	116.15 (7)	H9A—C9—H9B	109.5
C5—C4—C3	117.24 (7)	C8—C9—H9C	109.5
C6—C5—C4	122.23 (7)	H9A—C9—H9C	109.5
C6—C5—N1	117.47 (7)	H9B—C9—H9C	109.5
C6—C1—C2—C3	0.78 (12)	C3—C4—C5—N1	−177.86 (7)
C8—C1—C2—C3	−178.74 (7)	O5—N1—C5—C6	0.14 (12)
C7—O2—C3—C2	2.89 (12)	O4—N1—C5—C6	−179.69 (7)
C7—O2—C3—C4	−177.15 (7)	O5—N1—C5—C4	179.34 (8)
C1—C2—C3—O2	179.60 (8)	O4—N1—C5—C4	−0.48 (12)
C1—C2—C3—C4	−0.36 (12)	C2—C1—C6—C5	−0.15 (12)
O2—C3—C4—O1	−0.18 (10)	C8—C1—C6—C5	179.35 (7)
C2—C3—C4—O1	179.78 (7)	C4—C5—C6—C1	−0.92 (12)
O2—C3—C4—C5	179.38 (7)	N1—C5—C6—C1	178.27 (7)
C2—C3—C4—C5	−0.66 (12)	C6—C1—C8—O3	174.11 (8)
O1—C4—C5—C6	−179.19 (8)	C2—C1—C8—O3	−6.38 (12)
C3—C4—C5—C6	1.31 (12)	C6—C1—C8—C9	−5.00 (12)
O1—C4—C5—N1	1.65 (13)	C2—C1—C8—C9	174.51 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O4	0.878 (14)	1.850 (15)	2.5939 (10)	141.3 (13)
O1—H1O···O3i	0.878 (14)	2.271 (14)	2.8660 (9)	124.9 (12)
C2—H2···O4ii	0.952 (12)	2.439 (12)	3.3831 (12)	171.4 (11)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O4	0.878 (14)	1.850 (15)	2.5939 (10)	141.3 (13)
O1—H1O⋯O3i	0.878 (14)	2.271 (14)	2.8660 (9)	124.9 (12)
C2—H2⋯O4ii	0.952 (12)	2.439 (12)	3.3831 (12)	171.4 (11)

Symmetry codes: (i) ; (ii) .