4-Nitro-phenol-2,4,6-triamino-1,3,5-triazine-water (2/1/1).

In the title adduct, 2C(6)H(5)NO(3)·C(3)H(6)N(6)·H(2)O, the melamine and the two independent nitrophenol molecules are essentially planar, with maximum deviations of 0.0294 (10), 0.0706 (12) and 0.0742 (12) Å, respectively. In the crystal, N-H⋯N, O-H⋯N, N-H⋯O and O-H⋯O hydrogen bonds link the components into a three-dimensional network. In addition, weak π-π inter-actions [centroid-centroid distances = 3.728 (3) and 3.749 (3) Å] are observed.

Related literature

For applications of melamine, see: Cook et al. (2005 ▶); Rima et al. (2008 ▶). For a related structure, see: Cousson et al. (2005 ▶).

Experimental

Crystal data

2C6H5NO3·C3H6N6·H2O

M = 422.37

Triclinic,

a = 7.123 (5) Å

b = 10.577 (4) Å

c = 13.680 (5) Å

α = 68.256 (5)°

β = 88.772 (6)°

γ = 76.604 (5)°

V = 928.9 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 295 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.964, T max = 0.976

21610 measured reflections

5696 independent reflections

4164 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.122

S = 1.03

5696 reflections

311 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812029066/lh5493sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029066/lh5493Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029066/lh5493Isup3.cml

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

2C6H5NO3·C3H6N6·H2O	Z = 2
Mr = 422.37	F(000) = 440
Triclinic, P1	Dx = 1.510 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.123 (5) Å	Cell parameters from 21610 reflections
b = 10.577 (4) Å	θ = 2.1–30.7°
c = 13.680 (5) Å	µ = 0.12 mm−1
α = 68.256 (5)°	T = 295 K
β = 88.772 (6)°	Block, yellow
γ = 76.604 (5)°	0.30 × 0.20 × 0.20 mm
V = 928.9 (8) Å3

Bruker Kappa APEXII diffractometer	5696 independent reflections
Radiation source: fine-focus sealed tube	4164 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω and φ scans	θmax = 30.7°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→10
Tmin = 0.964, Tmax = 0.976	k = −15→15
21610 measured reflections	l = −17→19

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0598P)2 + 0.1276P] where P = (Fo2 + 2Fc2)/3
5696 reflections	(Δ/σ)max < 0.001
311 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq
C1	−0.33225 (16)	0.07164 (12)	0.40065 (10)	0.0341 (2)
C2	−0.24544 (16)	−0.05332 (12)	0.48003 (9)	0.0348 (2)
H2	−0.1702	−0.0549	0.5354	0.042*
C3	−0.27246 (18)	−0.17603 (13)	0.47577 (9)	0.0370 (3)
H3	−0.2136	−0.2617	0.5281	0.044*
C4	−0.38715 (18)	−0.17217 (13)	0.39367 (10)	0.0378 (3)
C5	−0.47281 (18)	−0.04548 (15)	0.31426 (10)	0.0423 (3)
H5	−0.5486	−0.0437	0.2590	0.051*
C6	−0.44573 (17)	0.07743 (14)	0.31718 (10)	0.0406 (3)
H6	−0.5024	0.1630	0.2642	0.049*
C7	−0.16167 (17)	−0.02771 (12)	0.09893 (9)	0.0345 (2)
C8	−0.20456 (18)	0.11701 (13)	0.05818 (10)	0.0394 (3)
H8	−0.2801	0.1679	−0.0049	0.047*
C9	−0.13380 (19)	0.18491 (12)	0.11231 (10)	0.0387 (3)
H9	−0.1618	0.2824	0.0860	0.046*
C10	−0.02072 (16)	0.10786 (12)	0.20608 (9)	0.0331 (2)
C11	0.01838 (17)	−0.03791 (12)	0.24690 (10)	0.0357 (2)
H11	0.0921	−0.0892	0.3105	0.043*
C12	−0.05206 (17)	−0.10608 (12)	0.19311 (10)	0.0361 (3)
H12	−0.0263	−0.2035	0.2197	0.043*
C13	0.26472 (17)	0.45692 (12)	0.11080 (9)	0.0339 (2)
C14	0.36186 (16)	0.58004 (11)	0.19500 (9)	0.0305 (2)
C15	0.10688 (16)	0.48525 (11)	0.24878 (9)	0.0322 (2)
N1	−0.30636 (15)	0.20134 (11)	0.40532 (10)	0.0443 (3)
N2	−0.22950 (16)	−0.10017 (13)	0.04030 (9)	0.0447 (3)
N3	0.38541 (14)	0.53546 (10)	0.11487 (7)	0.0338 (2)
N4	0.22586 (14)	0.55802 (10)	0.26462 (7)	0.0329 (2)
N5	0.12224 (14)	0.42855 (10)	0.17511 (8)	0.0359 (2)
N6	0.2906 (2)	0.40378 (15)	0.03568 (10)	0.0538 (3)
N7	0.48129 (18)	0.65529 (12)	0.20504 (10)	0.0444 (3)
N8	−0.03642 (18)	0.46571 (13)	0.31286 (10)	0.0465 (3)
O1	−0.42179 (18)	−0.28988 (12)	0.38794 (9)	0.0562 (3)
O2	−0.21683 (16)	0.19698 (11)	0.48256 (9)	0.0566 (3)
O3	−0.37293 (19)	0.31089 (11)	0.33173 (12)	0.0782 (4)
O4	0.05318 (15)	0.16839 (10)	0.26239 (8)	0.0464 (2)
O5	−0.31476 (16)	−0.03215 (14)	−0.04647 (9)	0.0633 (3)
O6	−0.19394 (18)	−0.22987 (12)	0.08023 (9)	0.0632 (3)
O7	0.23235 (17)	0.53850 (11)	0.47450 (9)	0.0526 (3)
H1	−0.357 (3)	−0.370 (3)	0.4389 (18)	0.093 (7)*
H4	0.054 (3)	0.257 (2)	0.2186 (15)	0.071 (5)*
H6A	0.216 (3)	0.353 (2)	0.0306 (14)	0.063 (5)*
H6B	0.378 (3)	0.4227 (19)	−0.0065 (14)	0.060 (5)*
H7A	0.243 (3)	0.555 (2)	0.4067 (17)	0.075 (6)*
H7B	0.252 (3)	0.607 (2)	0.4863 (17)	0.084 (6)*
H7C	0.576 (2)	0.6648 (17)	0.1643 (13)	0.054 (5)*
H7D	0.478 (2)	0.6781 (18)	0.2619 (15)	0.061 (5)*
H8A	−0.119 (2)	0.4277 (18)	0.3014 (14)	0.058 (5)*
H8B	−0.048 (2)	0.4994 (19)	0.3622 (15)	0.062 (5)*

	U11	U22	U33	U12	U13	U23
C1	0.0295 (5)	0.0342 (6)	0.0400 (6)	−0.0099 (4)	0.0057 (4)	−0.0143 (5)
C2	0.0353 (5)	0.0380 (6)	0.0333 (6)	−0.0102 (5)	0.0008 (4)	−0.0151 (5)
C3	0.0442 (6)	0.0343 (6)	0.0329 (6)	−0.0094 (5)	0.0004 (5)	−0.0129 (5)
C4	0.0430 (6)	0.0430 (7)	0.0358 (6)	−0.0153 (5)	0.0064 (5)	−0.0214 (5)
C5	0.0385 (6)	0.0548 (8)	0.0365 (6)	−0.0139 (6)	−0.0014 (5)	−0.0188 (6)
C6	0.0329 (6)	0.0422 (7)	0.0389 (6)	−0.0057 (5)	−0.0015 (5)	−0.0083 (5)
C7	0.0374 (6)	0.0389 (6)	0.0356 (6)	−0.0163 (5)	0.0085 (5)	−0.0195 (5)
C8	0.0446 (6)	0.0391 (6)	0.0321 (6)	−0.0115 (5)	−0.0014 (5)	−0.0098 (5)
C9	0.0485 (7)	0.0279 (5)	0.0376 (6)	−0.0099 (5)	0.0000 (5)	−0.0093 (5)
C10	0.0371 (6)	0.0324 (5)	0.0344 (6)	−0.0131 (4)	0.0055 (4)	−0.0151 (5)
C11	0.0384 (6)	0.0312 (6)	0.0350 (6)	−0.0080 (5)	−0.0002 (5)	−0.0096 (5)
C12	0.0418 (6)	0.0271 (5)	0.0409 (6)	−0.0099 (4)	0.0070 (5)	−0.0135 (5)
C13	0.0448 (6)	0.0315 (5)	0.0297 (5)	−0.0136 (5)	−0.0005 (5)	−0.0134 (5)
C14	0.0394 (6)	0.0249 (5)	0.0281 (5)	−0.0092 (4)	−0.0024 (4)	−0.0100 (4)
C15	0.0380 (6)	0.0265 (5)	0.0317 (5)	−0.0073 (4)	0.0008 (4)	−0.0105 (4)
N1	0.0362 (5)	0.0353 (5)	0.0616 (7)	−0.0111 (4)	0.0050 (5)	−0.0169 (5)
N2	0.0466 (6)	0.0588 (7)	0.0475 (6)	−0.0282 (5)	0.0158 (5)	−0.0326 (6)
N3	0.0446 (5)	0.0344 (5)	0.0288 (5)	−0.0170 (4)	0.0032 (4)	−0.0148 (4)
N4	0.0412 (5)	0.0300 (5)	0.0322 (5)	−0.0104 (4)	0.0028 (4)	−0.0160 (4)
N5	0.0440 (5)	0.0357 (5)	0.0360 (5)	−0.0178 (4)	0.0036 (4)	−0.0175 (4)
N6	0.0714 (8)	0.0706 (8)	0.0509 (7)	−0.0428 (7)	0.0212 (6)	−0.0438 (7)
N7	0.0581 (7)	0.0516 (7)	0.0411 (6)	−0.0309 (6)	0.0084 (5)	−0.0269 (5)
N8	0.0490 (6)	0.0521 (7)	0.0498 (7)	−0.0222 (5)	0.0158 (5)	−0.0265 (6)
O1	0.0798 (7)	0.0498 (6)	0.0523 (6)	−0.0234 (6)	−0.0038 (6)	−0.0293 (5)
O2	0.0633 (6)	0.0503 (6)	0.0687 (7)	−0.0224 (5)	0.0021 (5)	−0.0310 (5)
O3	0.0767 (8)	0.0327 (5)	0.1046 (10)	−0.0105 (5)	−0.0261 (7)	−0.0024 (6)
O4	0.0633 (6)	0.0399 (5)	0.0426 (5)	−0.0224 (4)	−0.0035 (4)	−0.0166 (4)
O5	0.0642 (7)	0.0895 (9)	0.0527 (6)	−0.0272 (6)	−0.0010 (5)	−0.0398 (6)
O6	0.0876 (8)	0.0572 (6)	0.0702 (7)	−0.0425 (6)	0.0180 (6)	−0.0382 (6)
O7	0.0817 (7)	0.0497 (6)	0.0421 (6)	−0.0346 (5)	0.0143 (5)	−0.0242 (5)

C1—C2	1.3766 (17)	C13—N6	1.3333 (16)
C1—C6	1.3877 (18)	C13—N3	1.3414 (14)
C1—N1	1.4501 (16)	C13—N5	1.3421 (16)
C2—C3	1.3774 (17)	C14—N7	1.3326 (15)
C2—H2	0.9300	C14—N3	1.3381 (14)
C3—C4	1.3857 (17)	C14—N4	1.3418 (16)
C3—H3	0.9300	C15—N8	1.3335 (17)
C4—O1	1.3538 (15)	C15—N4	1.3384 (15)
C4—C5	1.3852 (19)	C15—N5	1.3416 (15)
C5—C6	1.3726 (19)	N1—O3	1.2176 (16)
C5—H5	0.9300	N1—O2	1.2266 (16)
C6—H6	0.9300	N2—O5	1.2212 (17)
C7—C8	1.3804 (18)	N2—O6	1.2386 (17)
C7—C12	1.3815 (18)	N6—H6A	0.860 (18)
C7—N2	1.4518 (15)	N6—H6B	0.845 (18)
C8—C9	1.3770 (17)	N7—H7C	0.867 (17)
C8—H8	0.9300	N7—H7D	0.894 (19)
C9—C10	1.3871 (18)	N8—H8A	0.830 (17)
C9—H9	0.9300	N8—H8B	0.867 (19)
C10—O4	1.3488 (14)	O1—H1	0.90 (2)
C10—C11	1.3915 (17)	O4—H4	0.91 (2)
C11—C12	1.3747 (17)	O7—H7A	0.88 (2)
C11—H11	0.9300	O7—H7B	0.84 (2)
C12—H12	0.9300
C2—C1—C6	122.08 (11)	C11—C12—C7	119.00 (11)
C2—C1—N1	118.88 (11)	C11—C12—H12	120.5
C6—C1—N1	119.04 (11)	C7—C12—H12	120.5
C1—C2—C3	118.59 (11)	N6—C13—N3	116.17 (11)
C1—C2—H2	120.7	N6—C13—N5	118.22 (11)
C3—C2—H2	120.7	N3—C13—N5	125.61 (10)
C2—C3—C4	120.13 (11)	N7—C14—N3	117.08 (11)
C2—C3—H3	119.9	N7—C14—N4	117.29 (10)
C4—C3—H3	119.9	N3—C14—N4	125.61 (10)
O1—C4—C5	117.44 (12)	N8—C15—N4	117.07 (11)
O1—C4—C3	122.07 (12)	N8—C15—N5	117.58 (11)
C5—C4—C3	120.48 (11)	N4—C15—N5	125.34 (10)
C6—C5—C4	119.93 (12)	O3—N1—O2	122.26 (12)
C6—C5—H5	120.0	O3—N1—C1	118.70 (12)
C4—C5—H5	120.0	O2—N1—C1	119.04 (11)
C5—C6—C1	118.78 (12)	O5—N2—O6	122.77 (11)
C5—C6—H6	120.6	O5—N2—C7	119.29 (12)
C1—C6—H6	120.6	O6—N2—C7	117.92 (12)
C8—C7—C12	121.83 (10)	C14—N3—C13	114.25 (10)
C8—C7—N2	119.31 (12)	C15—N4—C14	114.57 (10)
C12—C7—N2	118.84 (11)	C15—N5—C13	114.40 (9)
C9—C8—C7	118.99 (11)	C13—N6—H6A	118.8 (12)
C9—C8—H8	120.5	C13—N6—H6B	119.2 (12)
C7—C8—H8	120.5	H6A—N6—H6B	122.0 (17)
C8—C9—C10	119.96 (11)	C14—N7—H7C	118.7 (11)
C8—C9—H9	120.0	C14—N7—H7D	118.9 (11)
C10—C9—H9	120.0	H7C—N7—H7D	121.0 (15)
O4—C10—C9	122.67 (11)	C15—N8—H8A	119.2 (12)
O4—C10—C11	117.05 (11)	C15—N8—H8B	119.5 (11)
C9—C10—C11	120.27 (10)	H8A—N8—H8B	121.1 (16)
C12—C11—C10	119.93 (12)	C4—O1—H1	114.2 (14)
C12—C11—H11	120.0	C10—O4—H4	107.8 (12)
C10—C11—H11	120.0	H7A—O7—H7B	108.7 (19)
C6—C1—C2—C3	0.14 (18)	C2—C1—N1—O3	175.39 (13)
N1—C1—C2—C3	179.25 (11)	C6—C1—N1—O3	−5.47 (18)
C1—C2—C3—C4	−0.89 (18)	C2—C1—N1—O2	−3.93 (17)
C2—C3—C4—O1	−178.18 (11)	C6—C1—N1—O2	175.21 (11)
C2—C3—C4—C5	1.15 (18)	C8—C7—N2—O5	3.71 (17)
O1—C4—C5—C6	178.73 (12)	C12—C7—N2—O5	−174.89 (11)
C3—C4—C5—C6	−0.63 (19)	C8—C7—N2—O6	−177.86 (11)
C4—C5—C6—C1	−0.12 (18)	C12—C7—N2—O6	3.55 (17)
C2—C1—C6—C5	0.37 (18)	N7—C14—N3—C13	178.15 (11)
N1—C1—C6—C5	−178.74 (11)	N4—C14—N3—C13	−3.37 (16)
C12—C7—C8—C9	0.89 (18)	N6—C13—N3—C14	−176.36 (11)
N2—C7—C8—C9	−177.66 (11)	N5—C13—N3—C14	3.84 (17)
C7—C8—C9—C10	0.24 (19)	N8—C15—N4—C14	−177.10 (11)
C8—C9—C10—O4	179.76 (12)	N5—C15—N4—C14	4.13 (17)
C8—C9—C10—C11	−1.32 (18)	N7—C14—N4—C15	178.19 (11)
O4—C10—C11—C12	−179.73 (11)	N3—C14—N4—C15	−0.29 (16)
C9—C10—C11—C12	1.29 (18)	N8—C15—N5—C13	177.51 (11)
C10—C11—C12—C7	−0.18 (18)	N4—C15—N5—C13	−3.73 (17)
C8—C7—C12—C11	−0.92 (18)	N6—C13—N5—C15	179.61 (12)
N2—C7—C12—C11	177.64 (10)	N3—C13—N5—C15	−0.59 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O7i	0.90 (2)	1.76 (2)	2.6600 (18)	172 (2)
O4—H4···N5	0.91 (2)	1.87 (2)	2.7217 (16)	157 (2)
N6—H6A···O6ii	0.860 (18)	2.363 (19)	3.0276 (16)	134 (2)
N6—H6B···N3iii	0.845 (18)	2.235 (19)	3.080 (2)	178 (2)
O7—H7A···N4	0.88 (2)	1.94 (2)	2.8020 (18)	166 (2)
O7—H7B···O2iv	0.84 (2)	2.22 (2)	3.0424 (18)	164 (2)
N7—H7C···O6v	0.867 (17)	2.250 (17)	3.056 (2)	155 (2)
N7—H7D···O1v	0.894 (19)	2.049 (19)	2.8996 (17)	159 (2)
N8—H8A···O3	0.830 (17)	2.367 (18)	3.158 (2)	159 (2)
N8—H8B···O7iv	0.867 (19)	2.517 (18)	3.1890 (19)	135 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O7i	0.90 (2)	1.76 (2)	2.6600 (18)	172 (2)
O4—H4⋯N5	0.91 (2)	1.87 (2)	2.7217 (16)	157 (2)
O7—H7A⋯N4	0.88 (2)	1.94 (2)	2.8020 (18)	166 (2)
O7—H7B⋯O2iv	0.84 (2)	2.22 (2)	3.0424 (18)	164 (2)
N6—H6A⋯O6ii	0.860 (18)	2.363 (19)	3.0276 (16)	134 (2)
N6—H6B⋯N3iii	0.845 (18)	2.235 (19)	3.080 (2)	178 (2)
N7—H7C⋯O6v	0.867 (17)	2.250 (17)	3.056 (2)	155 (2)
N7—H7D⋯O1v	0.894 (19)	2.049 (19)	2.8996 (17)	159 (2)
N8—H8A⋯O3	0.830 (17)	2.367 (18)	3.158 (2)	159 (2)
N8—H8B⋯O7iv	0.867 (19)	2.517 (18)	3.1890 (19)	135 (2)

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