2-Amino-4-nitro-phenol monohydrate.

The title compound, C(6)H(6)N(2)O(3)·H(2)O, crystallizes with two formula units in the asymmetric unit. The mol-ecules are essentially planar with the nitro groups twisted slightly out of the ring planes [maximum deviations from the ring plane of 0.13 (2) and 0.22 (2) Å in the two mol-ecules]. The respective O-N-C-C torsion angles are 6.0 (4) and 12.5 (4)°. In the crystal structure, mol-ecules are linked by inter-molecular N-H⋯O, C-H⋯O, O-H⋯O and O-H⋯N inter-actions into a three-dimensional network.

Related literature

For the use of nitro­aromatics as inter­mediates in explosives, dyestuffs, pesticides and organic synthesis, see: Yan et al. (2006 ▶). For the occurrence of nitro­aromatics in industrial wastes and as direct pollutants in the environment, see: Yan et al. (2006 ▶); Soojhawon et al. (2005 ▶). For related structures, see: Tanak et al. (2010 ▶); Bi et al. (2009 ▶); Garden et al. (2004 ▶).

Experimental

Crystal data

C6H6N2O3·H2O

M = 172.14

Monoclinic,

a = 7.539 (5) Å

b = 21.436 (5) Å

c = 9.714 (5) Å

β = 99.328 (5)°

V = 1549.1 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.13 mm−1

T = 296 K

0.62 × 0.30 × 0.05 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.578, T max = 0.892

8719 measured reflections

3031 independent reflections

1598 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.116

S = 0.98

3031 reflections

242 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.21 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810035415/bt5342sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035415/bt5342Isup2.hkl

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

C6H6N2O3·H2O	F(000) = 720
Mr = 172.14	Dx = 1.476 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 7016 reflections
a = 7.539 (5) Å	θ = 1.9–27.3°
b = 21.436 (5) Å	µ = 0.13 mm−1
c = 9.714 (5) Å	T = 296 K
β = 99.328 (5)°	Prism, yellow
V = 1549.1 (13) Å3	0.62 × 0.30 × 0.05 mm
Z = 8

Stoe IPDS II diffractometer	3031 independent reflections
Radiation source: fine-focus sealed tube	1598 reflections with I > 2σ(I)
graphite	Rint = 0.069
Detector resolution: 6.67 pixels mm-1	θmax = 26.0°, θmin = 1.9°
rotation method scans	h = −7→9
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −26→26
Tmin = 0.578, Tmax = 0.892	l = −11→11
8719 measured 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)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.0426P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98	(Δ/σ)max < 0.001
3031 reflections	Δρmax = 0.17 e Å−3
242 parameters	Δρmin = −0.21 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0063 (11)

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
O3	0.6819 (3)	0.50238 (8)	0.1354 (2)	0.0700 (6)
H1	0.7078	0.4727	0.1882	0.105*
C11	0.4215 (3)	0.62410 (11)	0.4251 (3)	0.0524 (7)
O6	0.3203 (3)	0.52487 (8)	0.3513 (2)	0.0738 (6)
H7	0.2634	0.5061	0.2849	0.111*
C4	0.7466 (3)	0.55594 (11)	0.2003 (3)	0.0525 (7)
C5	0.7094 (3)	0.61040 (11)	0.1216 (3)	0.0521 (6)
C12	0.4337 (3)	0.68701 (11)	0.4013 (3)	0.0534 (7)
H12	0.4950	0.7129	0.4699	0.064*
O8	0.7879 (3)	0.39992 (9)	0.2795 (3)	0.0796 (7)
C2	0.9053 (4)	0.61399 (12)	0.3917 (3)	0.0581 (7)
H2	0.9702	0.6158	0.4816	0.070*
C10	0.3296 (3)	0.58634 (11)	0.3190 (3)	0.0540 (7)
N4	0.4880 (4)	0.59777 (11)	0.5561 (3)	0.0661 (7)
N2	0.6190 (4)	0.60576 (11)	−0.0165 (3)	0.0656 (7)
C1	0.8706 (4)	0.66709 (11)	0.3123 (3)	0.0543 (7)
C6	0.7737 (4)	0.66635 (11)	0.1799 (3)	0.0567 (7)
H6	0.7515	0.7033	0.1299	0.068*
O1	1.0411 (4)	0.72657 (11)	0.4830 (3)	0.0981 (8)
C3	0.8408 (4)	0.55795 (12)	0.3337 (3)	0.0580 (7)
H3	0.8612	0.5214	0.3853	0.070*
N3	0.3654 (4)	0.77812 (11)	0.2558 (3)	0.0690 (7)
N1	0.9413 (4)	0.72598 (12)	0.3708 (3)	0.0744 (8)
C9	0.2545 (4)	0.61152 (12)	0.1923 (3)	0.0612 (7)
H9	0.1966	0.5858	0.1219	0.073*
C8	0.2650 (4)	0.67473 (12)	0.1700 (3)	0.0614 (7)
H8	0.2126	0.6922	0.0856	0.074*
C7	0.3544 (4)	0.71151 (11)	0.2748 (3)	0.0540 (7)
O5	0.4692 (4)	0.80874 (9)	0.3407 (3)	0.0955 (8)
O4	0.2702 (3)	0.80249 (9)	0.1563 (3)	0.0911 (8)
O2	0.9015 (4)	0.77391 (10)	0.3045 (3)	0.1136 (10)
O7	0.1271 (4)	0.45374 (12)	0.1652 (4)	0.1135 (11)
H11	0.513 (6)	0.558 (2)	0.552 (5)	0.170*
H5	0.544 (7)	0.574 (2)	−0.025 (5)	0.170*
H10	0.584 (7)	0.620 (2)	0.603 (5)	0.170*
H4	0.564 (7)	0.641 (2)	−0.048 (5)	0.170*
H15	0.808 (7)	0.368 (2)	0.243 (6)	0.170*
H16	0.686 (7)	0.394 (2)	0.327 (5)	0.170*
H13	0.201 (7)	0.432 (2)	0.122 (6)	0.170*
H14	0.055 (7)	0.431 (2)	0.188 (6)	0.170*

	U11	U22	U33	U12	U13	U23
O3	0.0838 (15)	0.0491 (10)	0.0692 (13)	−0.0074 (9)	−0.0118 (11)	0.0001 (10)
C11	0.0552 (17)	0.0446 (14)	0.0573 (18)	0.0031 (11)	0.0091 (13)	0.0025 (13)
O6	0.0843 (16)	0.0441 (10)	0.0885 (15)	−0.0017 (9)	0.0006 (11)	−0.0001 (10)
C4	0.0559 (17)	0.0441 (14)	0.0555 (18)	−0.0012 (12)	0.0031 (13)	−0.0018 (14)
C5	0.0512 (16)	0.0507 (14)	0.0534 (17)	0.0033 (12)	0.0056 (13)	−0.0005 (14)
C12	0.0575 (18)	0.0436 (14)	0.0573 (18)	0.0006 (11)	0.0038 (13)	0.0024 (13)
O8	0.0979 (19)	0.0521 (11)	0.0887 (18)	0.0038 (11)	0.0145 (13)	0.0065 (11)
C2	0.0568 (17)	0.0612 (17)	0.0530 (17)	0.0036 (13)	−0.0011 (13)	−0.0075 (15)
C10	0.0549 (18)	0.0402 (13)	0.068 (2)	0.0042 (11)	0.0126 (14)	0.0023 (14)
N4	0.0814 (19)	0.0477 (12)	0.0641 (17)	0.0015 (12)	−0.0041 (13)	0.0101 (13)
N2	0.0727 (18)	0.0609 (14)	0.0581 (16)	0.0057 (12)	−0.0050 (13)	0.0039 (13)
C1	0.0514 (16)	0.0478 (14)	0.064 (2)	−0.0011 (12)	0.0099 (14)	−0.0135 (14)
C6	0.0570 (17)	0.0458 (14)	0.068 (2)	0.0048 (12)	0.0128 (15)	0.0029 (15)
O1	0.0942 (18)	0.0970 (17)	0.0998 (19)	−0.0290 (13)	0.0057 (15)	−0.0430 (16)
C3	0.0661 (19)	0.0492 (14)	0.0557 (19)	0.0042 (12)	0.0007 (14)	0.0026 (13)
N3	0.0799 (19)	0.0529 (14)	0.0747 (19)	0.0083 (13)	0.0136 (15)	0.0146 (15)
N1	0.0694 (19)	0.0599 (17)	0.096 (2)	−0.0080 (13)	0.0205 (17)	−0.0282 (17)
C9	0.0613 (18)	0.0606 (16)	0.0597 (18)	0.0016 (13)	0.0039 (14)	−0.0047 (15)
C8	0.0599 (19)	0.0641 (17)	0.0594 (19)	0.0103 (14)	0.0075 (14)	0.0096 (15)
C7	0.0526 (17)	0.0459 (13)	0.0635 (19)	0.0067 (12)	0.0097 (14)	0.0088 (14)
O5	0.122 (2)	0.0524 (12)	0.104 (2)	−0.0134 (12)	−0.0068 (16)	0.0133 (13)
O4	0.1057 (19)	0.0673 (13)	0.0949 (18)	0.0214 (12)	−0.0002 (14)	0.0300 (13)
O2	0.137 (2)	0.0485 (13)	0.149 (3)	−0.0033 (13)	0.0030 (19)	−0.0150 (15)
O7	0.105 (2)	0.0883 (18)	0.156 (3)	−0.0325 (14)	0.0474 (18)	−0.0539 (18)

O3—C4	1.361 (3)	N4—H11	0.88 (5)
O3—H1	0.8200	N4—H10	0.92 (5)
C11—C12	1.374 (3)	N2—H5	0.89 (5)
C11—C10	1.402 (4)	N2—H4	0.89 (5)
C11—N4	1.408 (4)	C1—C6	1.372 (4)
O6—C10	1.359 (3)	C1—N1	1.450 (3)
O6—H7	0.8200	C6—H6	0.9300
C4—C3	1.374 (4)	O1—N1	1.219 (4)
C4—C5	1.398 (3)	C3—H3	0.9300
C5—C6	1.380 (3)	N3—O4	1.223 (3)
C5—N2	1.406 (4)	N3—O5	1.230 (3)
C12—C7	1.380 (4)	N3—C7	1.444 (3)
C12—H12	0.9300	N1—O2	1.224 (3)
O8—H15	0.80 (5)	C9—C8	1.377 (4)
O8—H16	0.96 (5)	C9—H9	0.9300
C2—C1	1.376 (4)	C8—C7	1.374 (4)
C2—C3	1.382 (4)	C8—H8	0.9300
C2—H2	0.9300	O7—H13	0.89 (5)
C10—C9	1.378 (4)	O7—H14	0.78 (5)
C4—O3—H1	109.5	H5—N2—H4	112 (4)
C12—C11—C10	118.8 (2)	C6—C1—C2	122.7 (2)
C12—C11—N4	121.5 (3)	C6—C1—N1	118.9 (3)
C10—C11—N4	119.6 (2)	C2—C1—N1	118.4 (3)
C10—O6—H7	109.5	C1—C6—C5	119.5 (2)
O3—C4—C3	123.7 (2)	C1—C6—H6	120.2
O3—C4—C5	115.2 (2)	C5—C6—H6	120.2
C3—C4—C5	121.1 (2)	C4—C3—C2	120.4 (3)
C6—C5—C4	118.4 (2)	C4—C3—H3	119.8
C6—C5—N2	122.5 (2)	C2—C3—H3	119.8
C4—C5—N2	119.0 (2)	O4—N3—O5	122.0 (2)
C11—C12—C7	119.5 (3)	O4—N3—C7	119.0 (3)
C11—C12—H12	120.3	O5—N3—C7	119.1 (3)
C7—C12—H12	120.3	O1—N1—O2	121.6 (3)
H15—O8—H16	109 (4)	O1—N1—C1	119.6 (3)
C1—C2—C3	117.9 (2)	O2—N1—C1	118.7 (3)
C1—C2—H2	121.1	C8—C9—C10	120.0 (3)
C3—C2—H2	121.1	C8—C9—H9	120.0
O6—C10—C9	123.9 (3)	C10—C9—H9	120.0
O6—C10—C11	115.3 (2)	C7—C8—C9	118.8 (3)
C9—C10—C11	120.9 (2)	C7—C8—H8	120.6
C11—N4—H11	113 (3)	C9—C8—H8	120.6
C11—N4—H10	112 (3)	C8—C7—C12	122.0 (2)
H11—N4—H10	112 (4)	C8—C7—N3	120.3 (3)
C5—N2—H5	110 (3)	C12—C7—N3	117.7 (3)
C5—N2—H4	113 (3)	H13—O7—H14	109 (5)
O3—C4—C5—C6	−178.9 (2)	C5—C4—C3—C2	−1.8 (4)
C3—C4—C5—C6	1.6 (4)	C1—C2—C3—C4	0.6 (4)
O3—C4—C5—N2	−3.1 (4)	C6—C1—N1—O1	−173.4 (3)
C3—C4—C5—N2	177.4 (3)	C2—C1—N1—O1	6.0 (4)
C10—C11—C12—C7	0.6 (4)	C6—C1—N1—O2	5.2 (4)
N4—C11—C12—C7	−175.0 (2)	C2—C1—N1—O2	−175.4 (3)
C12—C11—C10—O6	−178.8 (2)	O6—C10—C9—C8	177.8 (2)
N4—C11—C10—O6	−3.2 (4)	C11—C10—C9—C8	−1.7 (4)
C12—C11—C10—C9	0.8 (4)	C10—C9—C8—C7	1.3 (4)
N4—C11—C10—C9	176.4 (3)	C9—C8—C7—C12	0.0 (4)
C3—C2—C1—C6	0.8 (4)	C9—C8—C7—N3	−179.0 (2)
C3—C2—C1—N1	−178.6 (2)	C11—C12—C7—C8	−1.0 (4)
C2—C1—C6—C5	−0.9 (4)	C11—C12—C7—N3	178.0 (2)
N1—C1—C6—C5	178.4 (2)	O4—N3—C7—C8	12.1 (4)
C4—C5—C6—C1	−0.3 (4)	O5—N3—C7—C8	−168.4 (3)
N2—C5—C6—C1	−175.9 (3)	O4—N3—C7—C12	−166.9 (3)
O3—C4—C3—C2	178.7 (2)	O5—N3—C7—C12	12.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H4···O2i	0.89 (5)	2.51 (5)	3.382 (3)	165 (4)
N2—H5···O3ii	0.89 (5)	2.47 (5)	3.317 (3)	159 (4)
N4—H10···O4iii	0.92 (5)	2.18 (5)	3.062 (3)	159 (4)
N4—H11···O6iv	0.88 (5)	2.28 (5)	3.064 (3)	147 (4)
O7—H13···N2ii	0.89 (5)	2.00 (5)	2.877 (4)	172 (5)
O7—H14···O8v	0.78 (5)	2.43 (5)	3.166 (4)	158 (5)
O8—H15···O2vi	0.80 (5)	2.55 (5)	3.102 (3)	127 (4)
O8—H15···O5vi	0.80 (5)	2.35 (5)	3.038 (3)	144 (5)
O8—H16···N4iv	0.96 (5)	1.88 (5)	2.821 (4)	164 (4)
C6—H6···O1i	0.93	2.47	3.304 (4)	150
C12—H12···O4iii	0.93	2.54	3.254 (4)	133
O3—H1···O8	0.82	1.85	2.657 (3)	169
O6—H7···O7	0.82	1.81	2.619 (4)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H4⋯O2i	0.89 (5)	2.51 (5)	3.382 (3)	165 (4)
N2—H5⋯O3ii	0.89 (5)	2.47 (5)	3.317 (3)	159 (4)
N4—H10⋯O4iii	0.92 (5)	2.18 (5)	3.062 (3)	159 (4)
N4—H11⋯O6iv	0.88 (5)	2.28 (5)	3.064 (3)	147 (4)
O7—H13⋯N2ii	0.89 (5)	2.00 (5)	2.877 (4)	172 (5)
O7—H14⋯O8v	0.78 (5)	2.43 (5)	3.166 (4)	158 (5)
O8—H15⋯O2vi	0.80 (5)	2.55 (5)	3.102 (3)	127 (4)
O8—H15⋯O5vi	0.80 (5)	2.35 (5)	3.038 (3)	144 (5)
O8—H16⋯N4iv	0.96 (5)	1.88 (5)	2.821 (4)	164 (4)
C6—H6⋯O1i	0.93	2.47	3.304 (4)	150
C12—H12⋯O4iii	0.93	2.54	3.254 (4)	133
O3—H1⋯O8	0.82	1.85	2.657 (3)	169
O6—H7⋯O7	0.82	1.81	2.619 (4)	168

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