2,4-Dinitro-1-naphthol.

In the title compound, C(10)H(6)N(2)O(5), the two fused rings are almost co-planar, with an r.m.s. deviation of 0.0163 Å. The nitro groups are oriented at dihedral angles of 2.62 (11) and 44.69 (11)° with respect to the plane of the parent fused rings. Intra-molecular O-H⋯O and C-H⋯O hydrogen bonds complete S(6) ring motifs. In the crystal, mol-ecules are linked into chains along [101] by inter-molecular O-H⋯O hydrogen bonds. π-π inter-actions [centroid-centroid distances = 3.6296 (15), 3.8104 (15) and 3.6513 (14) Å] might play a role in stabilizing the structure.

Related literature

For background to estrogens, see: Schwartz et al. (1995 ▶); O’Donnell et al. (2001) ▶. For related structures, see: Filipenko et al. (2001 ▶); Rozycka-Sokolowska et al. (2004 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). For π–π inter­actions, see: Janiak (2000 ▶).

Experimental

Crystal data

C10H6N2O5

M = 234.17

Monoclinic,

a = 7.0512 (10) Å

b = 16.3541 (19) Å

c = 8.7988 (10) Å

β = 111.452 (6)°

V = 944.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 296 K

0.32 × 0.14 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.978, T max = 0.982

6868 measured reflections

1684 independent reflections

1058 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.119

S = 1.00

1684 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810045034/dn2615sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045034/dn2615Isup2.hkl

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

C10H6N2O5	F(000) = 480
Mr = 234.17	Dx = 1.647 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1058 reflections
a = 7.0512 (10) Å	θ = 2.5–25.1°
b = 16.3541 (19) Å	µ = 0.14 mm−1
c = 8.7988 (10) Å	T = 296 K
β = 111.452 (6)°	Needle, brown
V = 944.4 (2) Å3	0.32 × 0.14 × 0.12 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	1684 independent reflections
Radiation source: fine-focus sealed tube	1058 reflections with I > 2σ(I)
graphite	Rint = 0.052
Detector resolution: 8.20 pixels mm-1	θmax = 25.1°, θmin = 2.5°
ω scans	h = −7→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −19→19
Tmin = 0.978, Tmax = 0.982	l = −10→10
6868 measured reflections

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) = 0.119	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.059P)2] where P = (Fo2 + 2Fc2)/3
1684 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.17 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	0.3884 (3)	0.45828 (13)	0.10925 (19)	0.0656 (6)
O2	0.6120 (3)	0.36519 (11)	0.1294 (2)	0.0663 (6)
O3	0.8511 (3)	0.26242 (11)	0.6881 (2)	0.0762 (7)
O4	1.0038 (3)	0.34485 (11)	0.8845 (2)	0.0735 (6)
O5	0.9984 (3)	0.49989 (10)	0.83341 (16)	0.0500 (5)
H5A	1.0356	0.4587	0.8896	0.060*
N1	0.5444 (3)	0.42063 (12)	0.1860 (2)	0.0441 (5)
N2	0.8995 (3)	0.33110 (13)	0.7401 (3)	0.0497 (6)
C1	0.8052 (3)	0.54453 (12)	0.5693 (2)	0.0313 (5)
C2	0.8467 (4)	0.62585 (14)	0.6216 (3)	0.0415 (6)
H2	0.9197	0.6370	0.7312	0.050*
C3	0.7809 (4)	0.68880 (14)	0.5131 (3)	0.0465 (7)
H3	0.8077	0.7426	0.5489	0.056*
C4	0.6744 (4)	0.67246 (15)	0.3500 (3)	0.0487 (7)
H4	0.6329	0.7157	0.2766	0.058*
C5	0.6283 (4)	0.59409 (15)	0.2936 (3)	0.0419 (6)
H5	0.5557	0.5848	0.1832	0.050*
C6	0.6905 (3)	0.52753 (13)	0.4024 (2)	0.0313 (5)
C7	0.6553 (3)	0.44389 (13)	0.3569 (2)	0.0334 (5)
C8	0.7224 (3)	0.38182 (13)	0.4646 (2)	0.0373 (6)
H8	0.6948	0.3279	0.4299	0.045*
C9	0.8335 (3)	0.39941 (13)	0.6284 (2)	0.0354 (6)
C10	0.8816 (3)	0.47868 (13)	0.6824 (2)	0.0345 (5)

	U11	U22	U33	U12	U13	U23
O1	0.0468 (12)	0.0892 (14)	0.0412 (10)	0.0043 (11)	−0.0071 (9)	−0.0067 (9)
O2	0.0875 (16)	0.0570 (12)	0.0489 (11)	0.0026 (11)	0.0184 (10)	−0.0192 (9)
O3	0.110 (2)	0.0391 (11)	0.0731 (13)	−0.0007 (11)	0.0256 (12)	0.0117 (9)
O4	0.0881 (16)	0.0695 (13)	0.0441 (11)	−0.0059 (11)	0.0017 (11)	0.0225 (9)
O5	0.0560 (12)	0.0565 (10)	0.0260 (9)	−0.0001 (9)	0.0012 (8)	0.0046 (7)
N1	0.0459 (14)	0.0488 (12)	0.0320 (11)	−0.0085 (11)	0.0075 (10)	−0.0052 (9)
N2	0.0521 (15)	0.0483 (14)	0.0490 (13)	0.0019 (11)	0.0190 (11)	0.0158 (10)
C1	0.0258 (13)	0.0386 (12)	0.0291 (11)	0.0020 (10)	0.0096 (9)	−0.0002 (9)
C2	0.0405 (15)	0.0446 (14)	0.0385 (13)	−0.0023 (11)	0.0132 (11)	−0.0055 (11)
C3	0.0493 (17)	0.0376 (14)	0.0519 (15)	0.0043 (12)	0.0175 (13)	0.0013 (11)
C4	0.0490 (17)	0.0448 (15)	0.0489 (15)	0.0094 (12)	0.0139 (13)	0.0142 (12)
C5	0.0368 (15)	0.0526 (15)	0.0317 (12)	0.0054 (12)	0.0070 (10)	0.0065 (11)
C6	0.0235 (12)	0.0401 (12)	0.0298 (11)	0.0026 (10)	0.0093 (9)	0.0016 (9)
C7	0.0267 (13)	0.0435 (13)	0.0272 (11)	−0.0026 (10)	0.0066 (9)	−0.0030 (10)
C8	0.0347 (14)	0.0384 (13)	0.0388 (13)	−0.0021 (11)	0.0137 (11)	−0.0017 (10)
C9	0.0337 (14)	0.0404 (13)	0.0321 (12)	0.0021 (10)	0.0120 (10)	0.0083 (10)
C10	0.0307 (13)	0.0474 (14)	0.0247 (11)	0.0008 (11)	0.0093 (10)	0.0021 (10)

O1—N1	1.225 (2)	C2—H2	0.9300
O2—N1	1.213 (2)	C3—C4	1.381 (3)
O3—N2	1.214 (3)	C3—H3	0.9300
O4—N2	1.234 (3)	C4—C5	1.370 (3)
O5—C10	1.328 (2)	C4—H4	0.9300
O5—H5A	0.8200	C5—C6	1.409 (3)
N1—C7	1.469 (3)	C5—H5	0.9300
N2—C9	1.448 (3)	C6—C7	1.421 (3)
C1—C2	1.403 (3)	C7—C8	1.351 (3)
C1—C6	1.421 (3)	C8—C9	1.395 (3)
C1—C10	1.431 (3)	C8—H8	0.9300
C2—C3	1.365 (3)	C9—C10	1.380 (3)
C10—O5—H5A	109.5	C4—C5—C6	120.2 (2)
O2—N1—O1	123.9 (2)	C4—C5—H5	119.9
O2—N1—C7	118.2 (2)	C6—C5—H5	119.9
O1—N1—C7	117.9 (2)	C5—C6—C7	124.98 (19)
O3—N2—O4	122.4 (2)	C5—C6—C1	118.0 (2)
O3—N2—C9	118.8 (2)	C7—C6—C1	117.00 (19)
O4—N2—C9	118.8 (2)	C8—C7—C6	123.06 (19)
C2—C1—C6	119.75 (19)	C8—C7—N1	116.25 (19)
C2—C1—C10	120.33 (19)	C6—C7—N1	120.68 (18)
C6—C1—C10	119.90 (19)	C7—C8—C9	119.3 (2)
C3—C2—C1	120.6 (2)	C7—C8—H8	120.3
C3—C2—H2	119.7	C9—C8—H8	120.3
C1—C2—H2	119.7	C10—C9—C8	121.60 (19)
C2—C3—C4	119.8 (2)	C10—C9—N2	120.89 (19)
C2—C3—H3	120.1	C8—C9—N2	117.5 (2)
C4—C3—H3	120.1	O5—C10—C9	125.07 (19)
C5—C4—C3	121.6 (2)	O5—C10—C1	115.92 (19)
C5—C4—H4	119.2	C9—C10—C1	119.00 (18)
C3—C4—H4	119.2
C6—C1—C2—C3	−1.1 (3)	O1—N1—C7—C6	−44.9 (3)
C10—C1—C2—C3	177.5 (2)	C6—C7—C8—C9	−0.7 (3)
C1—C2—C3—C4	−0.7 (4)	N1—C7—C8—C9	178.4 (2)
C2—C3—C4—C5	1.5 (4)	C7—C8—C9—C10	−1.9 (3)
C3—C4—C5—C6	−0.4 (4)	C7—C8—C9—N2	179.0 (2)
C4—C5—C6—C7	−178.5 (2)	O3—N2—C9—C10	178.8 (2)
C4—C5—C6—C1	−1.4 (3)	O4—N2—C9—C10	−1.5 (3)
C2—C1—C6—C5	2.1 (3)	O3—N2—C9—C8	−2.1 (3)
C10—C1—C6—C5	−176.42 (19)	O4—N2—C9—C8	177.6 (2)
C2—C1—C6—C7	179.44 (19)	C8—C9—C10—O5	−175.0 (2)
C10—C1—C6—C7	0.9 (3)	N2—C9—C10—O5	4.1 (3)
C5—C6—C7—C8	178.2 (2)	C8—C9—C10—C1	3.8 (3)
C1—C6—C7—C8	1.1 (3)	N2—C9—C10—C1	−177.11 (19)
C5—C6—C7—N1	−0.8 (3)	C2—C1—C10—O5	−2.9 (3)
C1—C6—C7—N1	−177.9 (2)	C6—C1—C10—O5	175.7 (2)
O2—N1—C7—C8	−43.7 (3)	C2—C1—C10—C9	178.2 (2)
O1—N1—C7—C8	136.1 (2)	C6—C1—C10—C9	−3.2 (3)
O2—N1—C7—C6	135.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O1i	0.82	2.53	3.006 (3)	118
O5—H5A···O4	0.82	1.87	2.573 (2)	142
O5—H5A···N2	0.82	2.47	2.892 (3)	113
C5—H5···O1	0.93	2.35	2.902 (3)	118

	Cg···Cg	ipd	sa
Cg1···Cg2i	3.6296 (15)	3.365	1.305
Cg1···Cg2ii	3.8104 (15)	3.552	1.323
Cg2···Cg2i	3.6513 (14)	3.378	1.386

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O1i	0.82	2.53	3.006 (3)	118
O5—H5A⋯O4	0.82	1.87	2.573 (2)	142
O5—H5A⋯N2	0.82	2.47	2.892 (3)	113
C5—H5⋯O1	0.93	2.35	2.902 (3)	118

Symmetry code: (i) .