2-Amino-4-nitro­phenol monohydrate

Tanak, H.; Erşahin, F.; Yavuz, M.; Büyükgüngör, O.

doi:10.1107/S1600536810035415

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2544

doi:10.1107/S1600536810035415

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2-Amino-4-nitrophenol monohydrate

Hasan Tanak,^a ^* Ferda Erşahin,^b Metin Yavuz ^a and Orhan Büyükgüngör ^a

^aDepartment of Physics, Faculty of Arts & Science, Ondokuz Mayıs University, TR-55139 Kurupelit-Samsun, Turkey, and ^bDepartment of Chemistry, Faculty of Arts & Science, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: htanak@omu.edu.tr

(Received 28 August 2010; accepted 2 September 2010; online 11 September 2010)

The title compound, C₆H₆N₂O₃·H₂O, crystallizes with two formula units in the asymmetric unit. The molecules 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 molecules]. The respective O—N—C—C torsion angles are 6.0 (4) and 12.5 (4)°. In the crystal structure, molecules are linked by intermolecular N—H⋯O, C—H⋯O, O—H⋯O and O—H⋯N interactions 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_r = 172.14
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.054
wR(F²) = 0.116
S = 0.98
3031 reflections
242 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.21 e Å⁻³

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⋯O6^iv	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⋯O8^v	0.78 (5)	2.43 (5)	3.166 (4)	158 (5)
O8—H15⋯O2^vi	0.80 (5)	2.55 (5)	3.102 (3)	127 (4)
O8—H15⋯O5^vi	0.80 (5)	2.35 (5)	3.038 (3)	144 (5)
O8—H16⋯N4^iv	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) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z; (iii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) -x+1, -y+1, -z+1; (v) x-1, y, z; (vi) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

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

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

checkCIF report

Comment top

Nitroaromatics are widely used either as materials or as intermediates in explosives, dyestuffs, pesticides and organic synthesis (Yan et al., 2006). Nitroaromatics occur as industrial wastes and direct pollutants in the environment, and are relatively soluble in water and detectable in rivers, ponds and soil (Yan et al., 2006; Soojhawon et al., 2005).

There is two independent molecules in the asymmetric unit of the title compound (I, Fig. 1). The bond lengths and angles in (I) have normal values, and are comparable with those in the related structures (Tanak et al., 2010; Bi et al., 2009; Garden et al., 2004). The aromatic ring systems are almost planar with the maximum deviation, 0.13 (2) Å for atom O1 in the ring system C1—C6 and -0.22 (2) Å for atom O4 in the ring system C7—C12.

In the crystal structure, the molecules are linked by intermolecular N—H···O, C—H···O, O—H···O and O—H···N interactions (see Table I) into a three-dimensional network.

Related literature top

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 top

The commercially available compound (Acros organics) was recrystallized from ethanol.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); 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).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and 50% probability diplacement ellipsoids.
	Fig. 2. The crystal packing of the title compound.

2-Amino-4-nitrophenol monohydrate top

Crystal data top

C₆H₆N₂O₃·H₂O	F(000) = 720
M_r = 172.14	D_x = 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

Data collection top

Stoe IPDS II diffractometer	3031 independent reflections
Radiation source: fine-focus sealed tube	1598 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.069
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.0°, θ_min = 1.9°
rotation method scans	h = −7→9
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −26→26
T_min = 0.578, T_max = 0.892	l = −11→11
8719 measured reflections

Refinement top

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(F_o²) + (0.0426P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max < 0.001
3031 reflections	Δρ_max = 0.17 e Å⁻³
242 parameters	Δρ_min = −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)

Crystal data top

C₆H₆N₂O₃·H₂O	V = 1549.1 (13) Å³
M_r = 172.14	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.539 (5) Å	µ = 0.13 mm⁻¹
b = 21.436 (5) Å	T = 296 K
c = 9.714 (5) Å	0.62 × 0.30 × 0.05 mm
β = 99.328 (5)°

Data collection top

Stoe IPDS II diffractometer	3031 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	1598 reflections with I > 2σ(I)
T_min = 0.578, T_max = 0.892	R_int = 0.069
8719 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	Δρ_max = 0.17 e Å⁻³
3031 reflections	Δρ_min = −0.21 e Å⁻³
242 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O6^iv	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···O8^v	0.78 (5)	2.43 (5)	3.166 (4)	158 (5)
O8—H15···O2^vi	0.80 (5)	2.55 (5)	3.102 (3)	127 (4)
O8—H15···O5^vi	0.80 (5)	2.35 (5)	3.038 (3)	144 (5)
O8—H16···N4^iv	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) x−1/2, −y+3/2, z−1/2; (ii) −x+1, −y+1, −z; (iii) x+1/2, −y+3/2, z+1/2; (iv) −x+1, −y+1, −z+1; (v) x−1, y, z; (vi) −x+3/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₆H₆N₂O₃·H₂O
M_r	172.14
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	7.539 (5), 21.436 (5), 9.714 (5)
β (°)	99.328 (5)
V (Å³)	1549.1 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.62 × 0.30 × 0.05

Data collection
Diffractometer	Stoe IPDS II diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.578, 0.892
No. of measured, independent and observed [I > 2σ(I)] reflections	8719, 3031, 1598
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.116, 0.98
No. of reflections	3031
No. of parameters	242
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.21

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

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···O6^iv	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···O8^v	0.78 (5)	2.43 (5)	3.166 (4)	158 (5)
O8—H15···O2^vi	0.80 (5)	2.55 (5)	3.102 (3)	127 (4)
O8—H15···O5^vi	0.80 (5)	2.35 (5)	3.038 (3)	144 (5)
O8—H16···N4^iv	0.96 (5)	1.88 (5)	2.821 (4)	164 (4)
C6—H6···O1ⁱ	0.93	2.47	3.304 (4)	150.0
C12—H12···O4ⁱⁱⁱ	0.93	2.54	3.254 (4)	133.3
O3—H1···O8	0.82	1.85	2.657 (3)	168.8
O6—H7···O7	0.82	1.81	2.619 (4)	168.3

Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) −x+1, −y+1, −z; (iii) x+1/2, −y+3/2, z+1/2; (iv) −x+1, −y+1, −z+1; (v) x−1, y, z; (vi) −x+3/2, y−1/2, −z+1/2.

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS II diffractometer (purchased under grant No. F279 of the University Research Fund).

References

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