3,5-Dinitro-pyridin-4(1H)-one monohydrate.

The three independent organic mol-ecules of 3,5-dinitro-pyridin-4(1H)-one monohydrate, C(5)H(3)N(3)O(5)·H(2)O, each feature an N-H⋯O(water) hydrogen bond. Each water mol-ecule serves as hydrogen-bond donor to two carbonyl O atoms; these hydrogen bonds give rise to a layer motif. Two of the three formula units lie on special positions of site symmetry 2.

Related literature

The parent pyridin-4-one homolog crystallizes with five pyridone and six water mol­ecules in the asymmetric unit; see: Jones (2001 ▶).

Experimental

Crystal data

C5H3N3O5·H2O

M = 203.12

Orthorhombic,

a = 21.728 (2) Å

b = 21.654 (2) Å

c = 6.5713 (5) Å

V = 3091.7 (4) Å3

Z = 16

Mo Kα radiation

μ = 0.16 mm−1

T = 293 (2) K

0.45 × 0.45 × 0.20 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: none

21800 measured reflections

3555 independent reflections

2852 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.123

S = 1.08

3555 reflections

281 parameters

10 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808024604/pk2110sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024604/pk2110Isup2.hkl

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

C5H3N3O5·H2O	F000 = 1664
Mr = 203.12	Dx = 1.746 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 6494 reflections
a = 21.728 (2) Å	θ = 2.7–27.9º
b = 21.654 (2) Å	µ = 0.16 mm−1
c = 6.5713 (5) Å	T = 293 (2) K
V = 3091.7 (4) Å3	Block, colorless
Z = 16	0.45 × 0.45 × 0.20 mm

Bruker APEXII diffractometer	3555 independent reflections
Radiation source: fine-focus sealed tube	2852 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.022
Detector resolution: 9 pixels mm-1	θmax = 27.5º
T = 293(2) K	θmin = 2.7º
φ and ω scans	h = −28→27
Absorption correction: none	k = −28→27
21800 measured reflections	l = −8→8

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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.0528P)2 + 1.6904P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
3555 reflections	Δρmax = 0.35 e Å−3
281 parameters	Δρmin = −0.31 e Å−3
10 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
O1	0.69961 (7)	0.46193 (6)	0.2892 (3)	0.0552 (4)
O2	0.62136 (6)	0.50982 (6)	0.4163 (3)	0.0464 (4)
O3	0.60319 (6)	0.62125 (6)	0.2292 (2)	0.0431 (4)
O4	0.61633 (6)	0.73545 (6)	0.0695 (3)	0.0486 (4)
O5	0.70310 (8)	0.77792 (8)	0.1081 (6)	0.1176 (12)
O6	0.60858 (6)	0.75858 (6)	0.5467 (3)	0.0496 (4)
O7	0.65774 (6)	0.67898 (7)	0.6579 (3)	0.0562 (4)
O8	0.5000	0.77618 (7)	0.7500	0.0389 (4)
O9	0.65904 (7)	0.92189 (7)	0.1991 (3)	0.0659 (5)
O10	0.61401 (6)	1.00203 (6)	0.0759 (3)	0.0482 (4)
O11	0.5000	1.02039 (7)	0.2500	0.0357 (4)
O1W	0.91543 (6)	0.62174 (6)	0.2293 (3)	0.0507 (4)
O2W	0.5000	0.46255 (9)	0.7500	0.0627 (7)
O3W	0.5000	0.70522 (8)	0.2500	0.0416 (5)
N1	0.67114 (7)	0.50953 (7)	0.3278 (3)	0.0360 (3)
N2	0.67066 (7)	0.73271 (7)	0.1089 (3)	0.0435 (4)
N3	0.79137 (7)	0.61956 (8)	0.1992 (3)	0.0434 (4)
N4	0.61008 (6)	0.70807 (7)	0.6311 (3)	0.0357 (3)
N5	0.5000	0.58686 (9)	0.7500	0.0376 (5)
N6	0.5000	0.83100 (9)	0.2500	0.0384 (5)
N7	0.61264 (7)	0.95139 (7)	0.1582 (3)	0.0377 (4)
C1	0.76100 (8)	0.56854 (9)	0.2549 (3)	0.0390 (4)
H1A	0.7829	0.5329	0.2857	0.047*
C2	0.69872 (8)	0.56805 (8)	0.2672 (3)	0.0315 (4)
C3	0.65995 (8)	0.62114 (7)	0.2208 (3)	0.0302 (4)
C4	0.69804 (8)	0.67347 (8)	0.1610 (3)	0.0337 (4)
C5	0.76066 (8)	0.67135 (9)	0.1539 (3)	0.0405 (4)
H5A	0.7825	0.7065	0.1169	0.049*
C6	0.55166 (8)	0.61756 (8)	0.7027 (3)	0.0345 (4)
H6A	0.5874	0.5957	0.6733	0.041*
C7	0.55244 (7)	0.68038 (7)	0.6972 (3)	0.0290 (4)
C8	0.5000	0.71922 (10)	0.7500	0.0269 (5)
C9	0.55223 (9)	0.86172 (8)	0.2128 (3)	0.0360 (4)
H9	0.5884	0.8398	0.1893	0.043*
C10	0.55324 (8)	0.92451 (7)	0.2090 (3)	0.0301 (4)
C11	0.5000	0.96327 (10)	0.2500	0.0278 (5)
H11	0.9376 (8)	0.6540 (6)	0.220 (4)	0.059 (7)*
H12	0.9385 (8)	0.5898 (6)	0.218 (4)	0.053 (7)*
H21	0.4680 (2)	0.4409 (7)	0.757 (4)	0.055 (7)*
H31	0.5318 (3)	0.6832 (7)	0.236 (4)	0.058 (7)*
H3	0.8306 (5)	0.6181 (10)	0.199 (4)	0.057 (7)*
H5	0.5000	0.5477 (5)	0.7500	0.051 (9)*
H6	0.5000	0.7915 (5)	0.2500	0.051 (9)*

	U11	U22	U33	U12	U13	U23
O1	0.0543 (9)	0.0322 (7)	0.0790 (12)	0.0112 (6)	0.0045 (8)	0.0018 (7)
O2	0.0369 (7)	0.0417 (7)	0.0607 (9)	−0.0020 (6)	0.0068 (7)	0.0077 (7)
O3	0.0218 (6)	0.0344 (7)	0.0730 (10)	0.0014 (5)	0.0029 (6)	0.0061 (6)
O4	0.0381 (7)	0.0401 (7)	0.0676 (10)	0.0086 (6)	−0.0039 (7)	0.0016 (7)
O5	0.0504 (10)	0.0435 (10)	0.259 (4)	−0.0121 (8)	−0.0082 (15)	0.0441 (15)
O6	0.0415 (7)	0.0392 (7)	0.0681 (10)	−0.0090 (6)	0.0128 (7)	0.0059 (7)
O7	0.0273 (7)	0.0575 (9)	0.0837 (12)	0.0076 (6)	0.0053 (7)	−0.0044 (8)
O8	0.0326 (9)	0.0211 (8)	0.0631 (13)	0.000	0.0069 (8)	0.000
O9	0.0304 (7)	0.0501 (9)	0.1171 (16)	0.0104 (6)	0.0009 (8)	0.0031 (9)
O10	0.0399 (7)	0.0372 (7)	0.0673 (10)	−0.0056 (6)	0.0073 (7)	0.0088 (7)
O11	0.0305 (9)	0.0199 (8)	0.0567 (12)	0.000	0.0020 (8)	0.000
O1W	0.0263 (7)	0.0294 (7)	0.0962 (13)	0.0008 (5)	−0.0054 (7)	0.0013 (7)
O2W	0.0296 (10)	0.0253 (9)	0.133 (2)	0.000	−0.0014 (12)	0.000
O3W	0.0286 (9)	0.0244 (8)	0.0719 (14)	0.000	0.0004 (9)	0.000
N1	0.0345 (8)	0.0322 (8)	0.0414 (9)	0.0028 (6)	−0.0042 (7)	0.0014 (6)
N2	0.0356 (8)	0.0335 (8)	0.0614 (11)	−0.0008 (6)	0.0060 (8)	0.0067 (7)
N3	0.0206 (7)	0.0488 (10)	0.0608 (11)	0.0008 (6)	−0.0006 (7)	0.0012 (8)
N4	0.0275 (7)	0.0353 (8)	0.0442 (9)	−0.0025 (6)	0.0039 (6)	−0.0084 (7)
N5	0.0434 (12)	0.0192 (9)	0.0503 (14)	0.000	0.0058 (10)	0.000
N6	0.0460 (13)	0.0188 (9)	0.0504 (13)	0.000	0.0006 (10)	0.000
N7	0.0293 (7)	0.0333 (8)	0.0505 (10)	0.0011 (6)	0.0040 (7)	−0.0052 (7)
C1	0.0282 (9)	0.0412 (10)	0.0476 (11)	0.0067 (7)	−0.0031 (8)	−0.0008 (8)
C2	0.0270 (8)	0.0305 (8)	0.0371 (9)	0.0010 (6)	−0.0011 (7)	−0.0017 (7)
C3	0.0237 (8)	0.0296 (8)	0.0374 (9)	0.0006 (6)	0.0012 (7)	−0.0023 (7)
C4	0.0264 (8)	0.0324 (9)	0.0424 (10)	0.0001 (7)	0.0008 (7)	0.0007 (7)
C5	0.0288 (9)	0.0410 (10)	0.0517 (12)	−0.0062 (7)	0.0027 (8)	0.0011 (9)
C6	0.0339 (9)	0.0289 (8)	0.0406 (10)	0.0063 (7)	0.0034 (7)	−0.0019 (7)
C7	0.0261 (8)	0.0269 (8)	0.0339 (9)	−0.0002 (6)	0.0009 (7)	−0.0015 (6)
C8	0.0258 (11)	0.0233 (10)	0.0316 (12)	0.000	−0.0020 (9)	0.000
C9	0.0387 (10)	0.0270 (8)	0.0421 (10)	0.0055 (7)	0.0003 (8)	−0.0018 (7)
C10	0.0296 (8)	0.0239 (8)	0.0369 (9)	0.0001 (6)	−0.0006 (7)	−0.0009 (6)
C11	0.0281 (11)	0.0228 (10)	0.0323 (12)	0.000	−0.0021 (9)	0.000

O1—N1	1.2285 (19)	N5—C6	1.341 (2)
O2—N1	1.228 (2)	N5—C6i	1.341 (2)
O3—C3	1.235 (2)	N5—H5	0.848 (10)
O4—N2	1.210 (2)	N6—C9	1.338 (2)
O5—N2	1.206 (2)	N6—C9ii	1.338 (2)
O6—N4	1.227 (2)	N6—H6	0.854 (10)
O7—N4	1.225 (2)	N7—C10	1.455 (2)
O8—C8	1.233 (3)	C1—C2	1.356 (2)
O9—N7	1.223 (2)	C1—H1A	0.9300
O10—N7	1.223 (2)	C2—C3	1.457 (2)
O11—C11	1.237 (3)	C3—C4	1.457 (2)
O1W—H11	0.851 (9)	C4—C5	1.362 (2)
O1W—H12	0.858 (9)	C5—H5A	0.9300
O2W—H21	0.840 (8)	C6—C7	1.361 (2)
O3W—H31	0.844 (8)	C6—H6A	0.9300
N1—C2	1.457 (2)	C7—C8	1.458 (2)
N2—C4	1.455 (2)	C8—C7i	1.458 (2)
N3—C1	1.338 (3)	C9—C10	1.360 (2)
N3—C5	1.338 (3)	C9—H9	0.9300
N3—H3	0.853 (10)	C10—C11	1.454 (2)
N4—C7	1.455 (2)	C11—C10ii	1.454 (2)
H11—O1W—H12	109.1 (14)	O3—C3—C4	125.31 (15)
O2—N1—O1	123.08 (16)	O3—C3—C2	124.72 (15)
O2—N1—C2	119.15 (14)	C4—C3—C2	109.97 (14)
O1—N1—C2	117.76 (15)	C5—C4—N2	115.48 (16)
O5—N2—O4	121.96 (17)	C5—C4—C3	123.38 (16)
O5—N2—C4	118.53 (17)	N2—C4—C3	121.12 (15)
O4—N2—C4	119.51 (15)	N3—C5—C4	121.24 (17)
C1—N3—C5	120.47 (16)	N3—C5—H5A	119.4
C1—N3—H3	117.6 (16)	C4—C5—H5A	119.4
C5—N3—H3	121.8 (16)	N5—C6—C7	120.80 (16)
O7—N4—O6	123.11 (15)	N5—C6—H6A	119.6
O7—N4—C7	118.20 (15)	C7—C6—H6A	119.6
O6—N4—C7	118.66 (14)	C6—C7—N4	115.51 (15)
C6—N5—C6i	120.6 (2)	C6—C7—C8	124.09 (16)
C6—N5—H5	119.71 (10)	N4—C7—C8	120.39 (14)
C6i—N5—H5	119.71 (10)	O8—C8—C7i	125.23 (9)
C9—N6—C9ii	120.4 (2)	O8—C8—C7	125.23 (9)
C9—N6—H6	119.82 (11)	C7i—C8—C7	109.54 (19)
C9ii—N6—H6	119.82 (10)	N6—C9—C10	120.94 (17)
O10—N7—O9	123.05 (16)	N6—C9—H9	119.5
O10—N7—C10	118.79 (14)	C10—C9—H9	119.5
O9—N7—C10	118.16 (16)	C9—C10—C11	124.11 (16)
N3—C1—C2	120.99 (17)	C9—C10—N7	114.74 (15)
N3—C1—H1A	119.5	C11—C10—N7	121.15 (14)
C2—C1—H1A	119.5	O11—C11—C10ii	125.25 (9)
C1—C2—N1	115.69 (15)	O11—C11—C10	125.25 (9)
C1—C2—C3	123.94 (16)	C10ii—C11—C10	109.50 (19)
N1—C2—C3	120.36 (14)
C5—N3—C1—C2	−0.1 (3)	C6i—N5—C6—C7	−1.47 (13)
N3—C1—C2—N1	179.48 (18)	N5—C6—C7—N4	−176.15 (14)
N3—C1—C2—C3	0.5 (3)	N5—C6—C7—C8	3.0 (3)
O2—N1—C2—C1	152.19 (18)	O7—N4—C7—C6	−26.7 (2)
O1—N1—C2—C1	−27.0 (3)	O6—N4—C7—C6	151.55 (18)
O2—N1—C2—C3	−28.8 (3)	O7—N4—C7—C8	154.12 (15)
O1—N1—C2—C3	151.95 (18)	O6—N4—C7—C8	−27.7 (2)
C1—C2—C3—O3	179.23 (19)	C6—C7—C8—O8	178.50 (13)
N1—C2—C3—O3	0.3 (3)	N4—C7—C8—O8	−2.34 (18)
C1—C2—C3—C4	−0.1 (3)	C6—C7—C8—C7i	−1.50 (13)
N1—C2—C3—C4	−179.00 (16)	N4—C7—C8—C7i	177.66 (18)
O5—N2—C4—C5	−16.1 (3)	C9ii—N6—C9—C10	−0.98 (13)
O4—N2—C4—C5	164.46 (19)	N6—C9—C10—C11	2.0 (3)
O5—N2—C4—C3	162.5 (3)	N6—C9—C10—N7	−177.52 (15)
O4—N2—C4—C3	−16.9 (3)	O10—N7—C10—C9	152.08 (18)
O3—C3—C4—C5	179.9 (2)	O9—N7—C10—C9	−27.5 (3)
C2—C3—C4—C5	−0.7 (3)	O10—N7—C10—C11	−27.5 (2)
O3—C3—C4—N2	1.4 (3)	O9—N7—C10—C11	152.96 (17)
C2—C3—C4—N2	−179.23 (17)	C9—C10—C11—O11	179.01 (13)
C1—N3—C5—C4	−0.7 (3)	N7—C10—C11—O11	−1.48 (19)
N2—C4—C5—N3	179.75 (19)	C9—C10—C11—C10ii	−0.99 (13)
C3—C4—C5—N3	1.2 (3)	N7—C10—C11—C10ii	178.52 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1w	0.85 (1)	1.86 (1)	2.703 (2)	172 (2)
N5—H5···O2w	0.85 (1)	1.84 (1)	2.692 (3)	180
N6—H6···O3w	0.85 (1)	1.87 (1)	2.723 (3)	180
O1w—H11···O8iii	0.85 (1)	2.04 (1)	2.878 (2)	168 (2)
O1w—H12···O11iv	0.86 (1)	2.02 (1)	2.866 (2)	168 (2)
O2w—H21···O3v	0.84 (1)	2.05 (1)	2.888 (2)	173 (1)
O3w—H31···O3	0.84 (1)	2.05 (1)	2.890 (2)	172 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1w	0.85 (1)	1.86 (1)	2.703 (2)	172 (2)
N5—H5⋯O2w	0.85 (1)	1.84 (1)	2.692 (3)	180
N6—H6⋯O3w	0.85 (1)	1.87 (1)	2.723 (3)	180
O1w—H11⋯O8i	0.85 (1)	2.04 (1)	2.878 (2)	168 (2)
O1w—H12⋯O11ii	0.86 (1)	2.02 (1)	2.866 (2)	168 (2)
O2w—H21⋯O3iii	0.84 (1)	2.05 (1)	2.888 (2)	173 (1)
O3w—H31⋯O3	0.84 (1)	2.05 (1)	2.890 (2)	172 (2)

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