3-Nitro­phenol–1,3,5-triazine-2,4,6-tri­amine (2/1)

Sangeetha, V.; Kanagathara, N.; Chakkaravarthi, G.; Marchewka, M.K.; Anbalagan, G.

doi:10.1107/S1600536813011148

organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page o827

doi:10.1107/S1600536813011148

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3-Nitrophenol–1,3,5-triazine-2,4,6-triamine (2/1)

V. Sangeetha,^a N. Kanagathara,^b G. Chakkaravarthi,^c ^* M.K. Marchewka ^d and G. Anbalagan ^e ^*

^aDepartment of Physics, D.G. Vaishnav College, Chennai 600 106, India, ^bDepartment of Physics, Vel Tech Multi Tech Dr Rangarajan Dr Sakunthala Engineering College, Chennai 600 062, India, ^cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, ^dInstitute of Low Temperature and Structure Research, Polish Academy of Sciences, 50-950 Wrocław, 2, PO Box 937, Poland, and ^eDepartment of Physics, Presidency College, Chennai 600 005, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com, anbu_24663@yahoo.co.in

(Received 29 March 2013; accepted 24 April 2013; online 4 May 2013)

The asymmetric unit of the title compound, C₃H₆N₆·2C₆H₅NO₃, contains one melamine and two 3-nitrophenol molecules. The mean planes of the 3-nitrophenol molecules are almost orthogonal to the plane of melamine, making dihedral angles of 82.77 (4) and 88.36 (5)°. In the crystal, molecules 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 interactions [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_r = 404.36
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.119
S = 1.03
4447 reflections
295 parameters
8 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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⋯O1^iv	0.87 (1)	2.25 (1)	2.9613 (16)	138 (15)
N7—H7A⋯O1^v	0.88 (1)	2.32 (1)	3.1600 (17)	159 (14)
N7—H7B⋯O4^vi	0.88 (1)	2.13 (1)	2.9180 (16)	149 (15)
C6—H6⋯Cg3^vii	0.93	2.95	3.7504 (18)	145
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x, -y+1, -z+1; (iv) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (vi) $[x+{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ ; (vii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813011148/bh2476sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813011148/bh2476Isup3.cml

checkCIF report

Comment top

Melamine (1,3,5-triazine-2,4,6-triamine) and its derivatives can develop well defined non-covalent supramolecular nanoarchitectures via multiple hydrogen bonds by self-assembly of components containing complementary arrays of hydrogen-bonding sites (Desiraju, 1990; Krische & Lehn, 2000). The geometric parameters of the title compound (Fig. 1) are comparable to those reported for similar structures (Kanagathara et al., 2012; Wang et al., 2007). The mean planes of the two nitrophenol molecules (C1···C6) and (C10···C15) are almost orthogonal to the melamine (N2/C7/N4/C9/N3/C8) molecule, with dihedral angles of 82.77 (4) and 88.36 (5)°, respectively.

The crystal packing of the title compound is influenced by intermolecular O—H···N, N—H···N and N—H···O hydrogen bonds, as well as weak C—H···π (Table 1 and Fig. 2) and π–π interactions: Cg1···Cg2 (x, 1/2-y, 3/2+z) distance of 3.9823 (9) Å; Cg2···Cg1 (-1/2+x, 1/2-y, 1-z) distance of 3.9823 (9) Å; Cg1···Cg2 (-x, 1-y, 1-z) distance of 4.2397 (9) Å; Cg3···Cg1 (1/2-x, 1/2+y, z) distance of 5.0406 (8) Å; where Cg1, Cg2 and Cg3 are the centroids of the rings C1···C6, C10···C15, and N2/C7/N4/C9/N3/C8, respectively.

Related literature top

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 top

Melamine (1.261 g, 10 mmol) was dissolved in 200 ml of hot distilled water. 3-Nitrophenol (1.391 g, 10 mmol) was dissolved in 100 ml of distilled water, separately. The 3-nitrophenol solution was added gently to the hot solution of melamine, and the mixture stirred well for nearly five hours to get an homogeneous solution. Water was then allowed to evaporate. Within few days, tiny transparent, yellowish crystals were formed.

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of the title compound viewed down the a axis. Hydrogen bonds are shown as dashed lines.

3-Nitrophenol–1,3,5-triazine-2,4,6-triamine (2/1) top

Crystal data top

C₃H₆N₆·2C₆H₅NO₃	F(000) = 1680
M_r = 404.36	D_x = 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

Data collection top

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

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.119	w = 1/[σ²(F_o²) + (0.0577P)² + 0.7906P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
4447 reflections	Δρ_max = 0.24 e Å⁻³
295 parameters	Δρ_min = −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

Crystal data top

C₃H₆N₆·2C₆H₅NO₃	V = 3572.8 (2) Å³
M_r = 404.36	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 15.5150 (6) Å	µ = 0.12 mm⁻¹
b = 12.9137 (6) Å	T = 295 K
c = 17.8323 (6) Å	0.28 × 0.24 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	4447 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3352 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.977	R_int = 0.028
19568 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	8 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.24 e Å⁻³
4447 reflections	Δρ_min = −0.20 e Å⁻³
295 parameters

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O1^iv	0.87 (1)	2.25 (1)	2.9613 (16)	138 (15)
N7—H7A···O1^v	0.88 (1)	2.32 (1)	3.1600 (17)	159 (14)
N7—H7B···O4^vi	0.88 (1)	2.13 (1)	2.9180 (16)	149 (15)
C6—H6···Cg3^vii	0.93	2.95	3.7504 (18)	145

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

Experimental details

Crystal data
Chemical formula	C₃H₆N₆·2C₆H₅NO₃
M_r	404.36
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	295
a, b, c (Å)	15.5150 (6), 12.9137 (6), 17.8323 (6)
V (Å³)	3572.8 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.28 × 0.24 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.967, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	19568, 4447, 3352
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.119, 1.03
No. of reflections	4447
No. of parameters	295
No. of restraints	8
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.20

Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the melamine triamine ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3ⁱ	0.835 (9)	1.857 (10)	2.6907 (14)	176 (2)
O4—H4A···N2ⁱⁱ	0.830 (9)	1.865 (10)	2.6876 (14)	170 (2)
N5—H5A···N4ⁱⁱⁱ	0.888 (9)	2.172 (10)	3.0594 (18)	178 (17)
N5—H5B···O1^iv	0.874 (9)	2.250 (14)	2.9613 (16)	138 (15)
N7—H7A···O1^v	0.881 (9)	2.321 (10)	3.1600 (17)	159 (14)
N7—H7B···O4^vi	0.878 (9)	2.131 (12)	2.9180 (16)	149 (15)
C6—H6···Cg3^vii	0.93	2.953	3.7504 (18)	145

Acknowledgements

The authors wish to acknowledge the SAIF, IIT Madras (India), for the data collection.

References

Bruker (2003). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Desiraju, G. R. (1990). In Crystal Engineering: The Design of Organic Solids. Amsterdam: Elsevier. Google Scholar
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Krische, M. J. & Lehn, J.-M. (2000). Struct. Bond. 96, 3–29. CrossRef CAS Google Scholar
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Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, G., Wu, W. & Zhuang, L. (2007). Acta Cryst. E63, m2552–m2553. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

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