3-Nitro-phenol-1,3,5-triazine-2,4,6-tri-amine (2/1).

The asymmetric unit of the title compound, C3H6N6·2C6H5NO3, contains one melamine and two 3-nitro-phenol mol-ecules. The mean planes of the 3-nitro-phenol mol-ecules are almost orthogonal to the plane of melamine, making dihedral angles of 82.77 (4) and 88.36 (5)°. In the crystal, mol-ecules are linked via O-H⋯N, N-H⋯N and N-H⋯O hydrogen bonds, forming a three-dimensional network. The crystal also features weak C-H⋯π and π-π inter-actions [centroid-centroid distance = 3.9823 (9) Å].

Related literature

For general background to melamine derivatives, see: Desiraju et al. (1990 ▶); Krische & Lehn (2000 ▶). For related structures, see: Kanagathara et al. (2012 ▶); Wang et al. (2007 ▶).

Experimental

Crystal data

C3H6N6·2C6H5NO3

M = 404.36

Orthorhombic,

a = 15.5150 (6) Å

b = 12.9137 (6) Å

c = 17.8323 (6) Å

V = 3572.8 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.12 mm−1

T = 295 K

0.28 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.967, T max = 0.977

19568 measured reflections

4447 independent reflections

3352 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.119

S = 1.03

4447 reflections

295 parameters

8 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813011148/bh2476sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813011148/bh2476Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813011148/bh2476Isup3.cml

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

C3H6N6·2C6H5NO3	F(000) = 1680
Mr = 404.36	Dx = 1.503 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4327 reflections
a = 15.5150 (6) Å	θ = 2.3–28.3°
b = 12.9137 (6) Å	µ = 0.12 mm−1
c = 17.8323 (6) Å	T = 295 K
V = 3572.8 (2) Å3	Block, yellow
Z = 8	0.28 × 0.24 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	4447 independent reflections
Radiation source: fine-focus sealed tube	3352 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω and φ scans	θmax = 28.3°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→13
Tmin = 0.967, Tmax = 0.977	k = −17→7
19568 measured reflections	l = −23→23

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0577P)2 + 0.7906P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
4447 reflections	Δρmax = 0.24 e Å−3
295 parameters	Δρmin = −0.20 e Å−3
8 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.0028 (5)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
C1	0.20295 (11)	0.13223 (11)	0.30457 (8)	0.0472 (4)
C2	0.18602 (9)	0.11918 (10)	0.22906 (8)	0.0406 (3)
H2	0.1305	0.1048	0.2123	0.049*
C3	0.25379 (9)	0.12802 (10)	0.17907 (8)	0.0365 (3)
C4	0.33676 (9)	0.14713 (12)	0.20566 (9)	0.0475 (4)
H4	0.3826	0.1521	0.1723	0.057*
C5	0.35064 (12)	0.15871 (14)	0.28162 (10)	0.0597 (5)
H5	0.4062	0.1712	0.2989	0.072*
C6	0.28408 (13)	0.15216 (13)	0.33219 (9)	0.0586 (5)
H6	0.2935	0.1609	0.3833	0.070*
C7	0.01234 (8)	0.66741 (10)	0.47227 (7)	0.0337 (3)
C8	0.08123 (8)	0.82016 (10)	0.49038 (7)	0.0337 (3)
C9	0.14073 (8)	0.67001 (10)	0.53192 (7)	0.0322 (3)
C10	−0.15540 (9)	0.60489 (10)	0.68536 (8)	0.0383 (3)
C11	−0.07322 (10)	0.59736 (15)	0.65597 (9)	0.0546 (4)
H11	−0.0643	0.5851	0.6052	0.066*
C12	−0.00506 (10)	0.60861 (16)	0.70459 (10)	0.0595 (5)
H12	0.0510	0.6040	0.6864	0.071*
C13	−0.01848 (9)	0.62665 (13)	0.78025 (9)	0.0464 (4)
H13	0.0283	0.6340	0.8124	0.056*
C14	−0.10170 (8)	0.63378 (10)	0.80810 (8)	0.0365 (3)
C15	−0.17126 (8)	0.62232 (10)	0.76020 (8)	0.0369 (3)
H15	−0.2274	0.6263	0.7782	0.044*
N1	0.13017 (13)	0.12490 (12)	0.35762 (9)	0.0659 (4)
N2	0.01376 (7)	0.77043 (9)	0.46051 (6)	0.0361 (3)
N3	0.14703 (7)	0.77395 (8)	0.52606 (6)	0.0354 (2)
N4	0.07430 (6)	0.61329 (8)	0.50739 (6)	0.0345 (3)
N5	−0.05479 (8)	0.61359 (11)	0.44621 (8)	0.0461 (3)
N6	0.08276 (9)	0.92415 (10)	0.48582 (8)	0.0457 (3)
N7	0.20470 (8)	0.61983 (10)	0.56654 (8)	0.0445 (3)
N8	−0.22955 (8)	0.59341 (10)	0.63461 (7)	0.0459 (3)
O1	0.23651 (6)	0.11610 (8)	0.10455 (6)	0.0433 (3)
O2	0.14494 (13)	0.13811 (14)	0.42402 (8)	0.1006 (6)
O3	0.05950 (11)	0.10386 (16)	0.33363 (10)	0.0968 (5)
O4	−0.11865 (7)	0.65065 (10)	0.88192 (6)	0.0537 (3)
O5	−0.30194 (7)	0.60094 (10)	0.66114 (7)	0.0583 (3)
O6	−0.21580 (9)	0.57499 (12)	0.56836 (6)	0.0716 (4)
H1	0.2744 (10)	0.1481 (14)	0.0807 (10)	0.068 (6)*
H4A	−0.0754 (9)	0.6682 (15)	0.9062 (9)	0.064 (6)*
H6A	0.0446 (9)	0.9511 (14)	0.4564 (9)	0.065 (5)*
H6B	0.1328 (8)	0.9538 (13)	0.4931 (10)	0.061 (5)*
H7A	0.2051 (10)	0.5516 (7)	0.5665 (9)	0.048 (4)*
H7B	0.2525 (8)	0.6534 (12)	0.5769 (9)	0.050 (5)*
H5A	−0.0593 (11)	0.5475 (8)	0.4593 (10)	0.061 (5)*
H5B	−0.1003 (8)	0.6483 (13)	0.4321 (10)	0.058 (5)*

	U11	U22	U33	U12	U13	U23
C1	0.0631 (10)	0.0362 (7)	0.0423 (8)	−0.0015 (7)	0.0035 (7)	0.0051 (6)
C2	0.0372 (7)	0.0385 (7)	0.0461 (7)	−0.0032 (6)	−0.0005 (6)	0.0041 (6)
C3	0.0350 (7)	0.0346 (6)	0.0398 (7)	−0.0048 (5)	−0.0051 (5)	0.0045 (5)
C4	0.0369 (8)	0.0514 (8)	0.0542 (8)	−0.0108 (6)	−0.0080 (7)	0.0107 (7)
C5	0.0587 (10)	0.0596 (10)	0.0608 (10)	−0.0195 (8)	−0.0260 (9)	0.0123 (8)
C6	0.0849 (13)	0.0476 (9)	0.0433 (8)	−0.0136 (8)	−0.0168 (9)	0.0063 (7)
C7	0.0258 (6)	0.0459 (7)	0.0293 (6)	0.0013 (5)	−0.0018 (5)	0.0003 (5)
C8	0.0298 (6)	0.0419 (7)	0.0295 (6)	0.0021 (5)	0.0051 (5)	0.0018 (5)
C9	0.0252 (6)	0.0416 (7)	0.0300 (6)	0.0001 (5)	−0.0010 (5)	0.0011 (5)
C10	0.0370 (7)	0.0373 (6)	0.0405 (7)	−0.0007 (5)	−0.0052 (6)	0.0000 (5)
C11	0.0469 (9)	0.0779 (11)	0.0391 (7)	0.0020 (8)	0.0061 (7)	−0.0013 (7)
C12	0.0330 (8)	0.0935 (13)	0.0520 (9)	0.0002 (8)	0.0107 (7)	−0.0027 (9)
C13	0.0281 (7)	0.0632 (9)	0.0479 (8)	−0.0024 (6)	−0.0015 (6)	−0.0034 (7)
C14	0.0300 (7)	0.0396 (6)	0.0399 (7)	−0.0037 (5)	0.0012 (5)	−0.0049 (5)
C15	0.0271 (6)	0.0389 (6)	0.0447 (7)	−0.0028 (5)	0.0000 (5)	−0.0056 (5)
N1	0.0904 (13)	0.0530 (8)	0.0543 (9)	0.0022 (8)	0.0230 (9)	0.0047 (7)
N2	0.0293 (6)	0.0447 (6)	0.0342 (5)	0.0039 (5)	−0.0022 (4)	0.0046 (4)
N3	0.0287 (5)	0.0406 (6)	0.0370 (6)	−0.0036 (4)	−0.0031 (4)	0.0018 (4)
N4	0.0259 (5)	0.0399 (6)	0.0377 (6)	0.0000 (4)	−0.0052 (4)	0.0012 (4)
N5	0.0306 (6)	0.0515 (7)	0.0561 (7)	−0.0013 (6)	−0.0156 (6)	0.0033 (6)
N6	0.0431 (8)	0.0406 (6)	0.0535 (7)	0.0022 (6)	0.0009 (6)	0.0055 (5)
N7	0.0294 (6)	0.0457 (7)	0.0585 (8)	−0.0017 (5)	−0.0150 (6)	0.0062 (6)
N8	0.0481 (8)	0.0436 (6)	0.0460 (7)	0.0003 (6)	−0.0104 (6)	−0.0007 (5)
O1	0.0350 (5)	0.0563 (6)	0.0386 (5)	−0.0122 (5)	−0.0010 (4)	0.0022 (4)
O2	0.1446 (16)	0.1092 (13)	0.0480 (8)	0.0043 (11)	0.0257 (9)	−0.0016 (8)
O3	0.0729 (10)	0.1297 (15)	0.0876 (11)	−0.0121 (10)	0.0340 (9)	−0.0054 (10)
O4	0.0298 (5)	0.0893 (8)	0.0421 (6)	−0.0117 (5)	0.0014 (4)	−0.0207 (5)
O5	0.0396 (6)	0.0704 (8)	0.0648 (7)	0.0011 (5)	−0.0132 (5)	−0.0101 (6)
O6	0.0719 (9)	0.1012 (10)	0.0417 (6)	0.0024 (8)	−0.0125 (6)	−0.0077 (6)

C1—C6	1.376 (2)	C10—N8	1.4712 (18)
C1—C2	1.382 (2)	C11—C12	1.375 (2)
C1—N1	1.476 (2)	C11—H11	0.9300
C2—C3	1.383 (2)	C12—C13	1.385 (2)
C2—H2	0.9300	C12—H12	0.9300
C3—O1	1.3644 (16)	C13—C14	1.3865 (19)
C3—C4	1.3938 (19)	C13—H13	0.9300
C4—C5	1.380 (2)	C14—O4	1.3599 (16)
C4—H4	0.9300	C14—C15	1.3842 (18)
C5—C6	1.374 (3)	C15—H15	0.9300
C5—H5	0.9300	N1—O3	1.208 (2)
C6—H6	0.9300	N1—O2	1.218 (2)
C7—N5	1.3356 (17)	N5—H5A	0.888 (9)
C7—N4	1.3434 (16)	N5—H5B	0.874 (9)
C7—N2	1.3469 (18)	N6—H6A	0.863 (9)
C8—N2	1.3385 (16)	N6—H6B	0.875 (9)
C8—N3	1.3429 (16)	N7—H7A	0.881 (9)
C8—N6	1.3456 (19)	N7—H7B	0.878 (9)
C9—N7	1.3364 (17)	N8—O5	1.2226 (16)
C9—N4	1.3380 (16)	N8—O6	1.2238 (17)
C9—N3	1.3498 (17)	O1—H1	0.835 (9)
C10—C15	1.3756 (19)	O4—H4A	0.830 (9)
C10—C11	1.382 (2)
C6—C1—C2	123.05 (15)	C11—C12—C13	121.09 (14)
C6—C1—N1	118.84 (15)	C11—C12—H12	119.5
C2—C1—N1	118.10 (15)	C13—C12—H12	119.5
C1—C2—C3	118.25 (14)	C12—C13—C14	120.01 (14)
C1—C2—H2	120.9	C12—C13—H13	120.0
C3—C2—H2	120.9	C14—C13—H13	120.0
O1—C3—C2	117.97 (12)	O4—C14—C15	117.63 (12)
O1—C3—C4	122.19 (13)	O4—C14—C13	122.51 (12)
C2—C3—C4	119.83 (13)	C15—C14—C13	119.86 (13)
C5—C4—C3	119.82 (15)	C10—C15—C14	118.47 (12)
C5—C4—H4	120.1	C10—C15—H15	120.8
C3—C4—H4	120.1	C14—C15—H15	120.8
C6—C5—C4	121.37 (15)	O3—N1—O2	123.13 (18)
C6—C5—H5	119.3	O3—N1—C1	118.81 (16)
C4—C5—H5	119.3	O2—N1—C1	118.04 (19)
C5—C6—C1	117.66 (15)	C8—N2—C7	115.13 (11)
C5—C6—H6	121.2	C8—N3—C9	115.05 (11)
C1—C6—H6	121.2	C9—N4—C7	114.76 (11)
N5—C7—N4	116.71 (12)	C7—N5—H5A	118.0 (12)
N5—C7—N2	118.20 (12)	C7—N5—H5B	117.7 (12)
N4—C7—N2	125.08 (11)	H5A—N5—H5B	120.4 (17)
N2—C8—N3	124.74 (12)	C8—N6—H6A	115.2 (13)
N2—C8—N6	117.95 (12)	C8—N6—H6B	116.3 (12)
N3—C8—N6	117.30 (12)	H6A—N6—H6B	121.5 (19)
N7—C9—N4	117.24 (12)	C9—N7—H7A	119.3 (11)
N7—C9—N3	117.65 (12)	C9—N7—H7B	119.0 (11)
N4—C9—N3	125.09 (11)	H7A—N7—H7B	119.2 (15)
C15—C10—C11	122.99 (13)	O5—N8—O6	123.30 (13)
C15—C10—N8	118.25 (12)	O5—N8—C10	118.19 (12)
C11—C10—N8	118.76 (13)	O6—N8—C10	118.50 (13)
C12—C11—C10	117.58 (14)	C3—O1—H1	107.5 (14)
C12—C11—H11	121.2	C14—O4—H4A	113.1 (13)
C10—C11—H11	121.2
C6—C1—C2—C3	−0.9 (2)	C6—C1—N1—O3	−177.46 (17)
N1—C1—C2—C3	178.75 (12)	C2—C1—N1—O3	2.9 (2)
C1—C2—C3—O1	−179.35 (12)	C6—C1—N1—O2	0.8 (2)
C1—C2—C3—C4	1.5 (2)	C2—C1—N1—O2	−178.81 (16)
O1—C3—C4—C5	179.91 (14)	N3—C8—N2—C7	3.86 (18)
C2—C3—C4—C5	−1.0 (2)	N6—C8—N2—C7	−174.73 (12)
C3—C4—C5—C6	−0.2 (3)	N5—C7—N2—C8	177.70 (12)
C4—C5—C6—C1	0.8 (3)	N4—C7—N2—C8	−3.47 (18)
C2—C1—C6—C5	−0.3 (2)	N2—C8—N3—C9	−1.28 (18)
N1—C1—C6—C5	−179.92 (14)	N6—C8—N3—C9	177.32 (12)
C15—C10—C11—C12	−0.4 (3)	N7—C9—N3—C8	179.61 (12)
N8—C10—C11—C12	179.86 (15)	N4—C9—N3—C8	−2.16 (18)
C10—C11—C12—C13	0.1 (3)	N7—C9—N4—C7	−179.26 (12)
C11—C12—C13—C14	−0.1 (3)	N3—C9—N4—C7	2.50 (18)
C12—C13—C14—O4	179.52 (15)	N5—C7—N4—C9	179.35 (12)
C12—C13—C14—C15	0.3 (2)	N2—C7—N4—C9	0.50 (18)
C11—C10—C15—C14	0.6 (2)	C15—C10—N8—O5	0.72 (19)
N8—C10—C15—C14	−179.63 (12)	C11—C10—N8—O5	−179.50 (14)
O4—C14—C15—C10	−179.81 (12)	C15—C10—N8—O6	−177.97 (14)
C13—C14—C15—C10	−0.6 (2)	C11—C10—N8—O6	1.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3i	0.84 (1)	1.86 (1)	2.6907 (14)	176 (2)
O4—H4A···N2ii	0.83 (1)	1.87 (1)	2.6876 (14)	170 (2)
N5—H5A···N4iii	0.89 (1)	2.17 (1)	3.0594 (18)	178 (17)
N5—H5B···O1iv	0.87 (1)	2.25 (1)	2.9613 (16)	138 (15)
N7—H7A···O1v	0.88 (1)	2.32 (1)	3.1600 (17)	159 (14)
N7—H7B···O4vi	0.88 (1)	2.13 (1)	2.9180 (16)	149 (15)
C6—H6···Cg3vii	0.93	2.95	3.7504 (18)	145

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the melamine tri­amine ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N3i	0.84 (1)	1.86 (1)	2.6907 (14)	176 (2)
O4—H4A⋯N2ii	0.83 (1)	1.87 (1)	2.6876 (14)	170 (2)
N5—H5A⋯N4iii	0.89 (1)	2.17 (1)	3.0594 (18)	178 (17)
N5—H5B⋯O1iv	0.87 (1)	2.25 (1)	2.9613 (16)	138 (15)
N7—H7A⋯O1v	0.88 (1)	2.32 (1)	3.1600 (17)	159 (14)
N7—H7B⋯O4vi	0.88 (1)	2.13 (1)	2.9180 (16)	149 (15)
C6—H6⋯Cg3vii	0.93	2.95	3.7504 (18)	145

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