Adipic acid-2,4-diamino-6-(4-meth-oxy-phen-yl)-1,3,5-triazine (1/2).

The asymmetric unit of the title compound, 2C(10)H(11)N(5)O·C(6)H(10)O(4), consists of a 2,4-diamino-6-(4-meth-oxy-phen-yl)-1,3,5-triazine mol-ecule and one-half mol-ecule of adipic acid which lies about an inversion center. The triazine ring makes a dihedral angle of 12.89 (4)° with the adjacent benzene ring. In the crystal, the components are linked by N-H⋯O and O-H⋯N hydrogen bonds, thus generating a centrosymmetric 2 + 1 unit of triazine and adipic acid mol-ecules with R(2) (2)(8) motifs. The triazine mol-ecules are connected to each other by N-H⋯N hydrogen bonds, forming an R(2) (2)(8) motif and a supra-molecular ribbon along the c axis. The 2 + 1 units and the supra-molecular ribbons are further inter-linked by weak N-H⋯O, C-H⋯O and C-H⋯π inter-actions, resulting in a three-dimensional network.

Related literature

For the biological activity of triazine derivatives, see: Bork et al. (2003 ▶). For bond-length data, see: Allen et al. (1987) ▶. For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

2C10H11N5O·C6H10O4

M = 580.62

Monoclinic,

a = 15.9952 (9) Å

b = 7.3104 (5) Å

c = 12.0351 (7) Å

β = 96.912 (1)°

V = 1397.05 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.64 × 0.40 × 0.22 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.938, T max = 0.979

13850 measured reflections

4993 independent reflections

4263 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.126

S = 1.08

4993 reflections

211 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.49 e Å−3

Δρmin = −0.22 e Å−3

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812038743/is5192sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038743/is5192Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812038743/is5192Isup3.cml

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

2C10H11N5O·C6H10O4	F(000) = 612
Mr = 580.62	Dx = 1.380 Mg m−3
Monoclinic, P2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yc	Cell parameters from 7141 reflections
a = 15.9952 (9) Å	θ = 2.8–32.4°
b = 7.3104 (5) Å	µ = 0.10 mm−1
c = 12.0351 (7) Å	T = 100 K
β = 96.912 (1)°	Block, colourless
V = 1397.05 (15) Å3	0.64 × 0.40 × 0.22 mm
Z = 2

Bruker SMART APEXII DUO CCD area-detector diffractometer	4993 independent reflections
Radiation source: fine-focus sealed tube	4263 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 32.6°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −24→24
Tmin = 0.938, Tmax = 0.979	k = −10→11
13850 measured reflections	l = −18→17

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0737P)2 + 0.2639P] where P = (Fo2 + 2Fc2)/3
4993 reflections	(Δ/σ)max = 0.001
211 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

	x	y	z	Uiso*/Ueq
O1	0.38325 (5)	0.96141 (10)	0.63437 (6)	0.02222 (15)
O2	0.39639 (4)	0.93287 (9)	0.45203 (5)	0.01924 (14)
O3	0.06629 (4)	1.28973 (9)	0.50394 (6)	0.01951 (14)
N1	0.24094 (4)	0.53425 (10)	0.66667 (5)	0.01295 (13)
N2	0.30198 (5)	0.29976 (11)	0.77505 (6)	0.01611 (14)
N3	0.30677 (4)	0.28034 (10)	0.58551 (5)	0.01296 (13)
N4	0.30393 (5)	0.26981 (11)	0.39410 (6)	0.01582 (14)
N5	0.24267 (4)	0.51829 (10)	0.46927 (5)	0.01320 (13)
C2	0.28291 (5)	0.37227 (11)	0.67348 (6)	0.01221 (14)
C4	0.28388 (5)	0.35704 (11)	0.48465 (6)	0.01227 (14)
C6	0.22262 (4)	0.59896 (11)	0.56262 (6)	0.01197 (14)
C7	0.17790 (5)	0.77580 (12)	0.54733 (6)	0.01294 (15)
C8	0.16892 (5)	0.89239 (12)	0.63761 (7)	0.01547 (15)
H8A	0.1896	0.8550	0.7114	0.019*
C9	0.13032 (5)	1.06136 (12)	0.62062 (7)	0.01631 (16)
H9A	0.1246	1.1387	0.6827	0.020*
C10	0.09974 (5)	1.11861 (12)	0.51240 (7)	0.01452 (15)
C11	0.10537 (5)	1.00202 (13)	0.42193 (7)	0.01636 (16)
H11A	0.0828	1.0379	0.3485	0.020*
C12	0.14445 (5)	0.83235 (12)	0.44012 (7)	0.01592 (15)
H12A	0.1485	0.7534	0.3783	0.019*
C13	0.04003 (6)	1.35766 (14)	0.39371 (8)	0.02142 (18)
H13A	0.0194	1.4833	0.3986	0.032*
H13B	−0.0052	1.2802	0.3572	0.032*
H13C	0.0878	1.3560	0.3499	0.032*
C14	0.40924 (5)	0.87581 (12)	0.54826 (7)	0.01502 (15)
C15	0.45564 (5)	0.70071 (12)	0.58066 (7)	0.01631 (16)
H15A	0.4198	0.6232	0.6230	0.020*
H15B	0.5074	0.7305	0.6311	0.020*
C16	0.47996 (5)	0.59149 (12)	0.48172 (7)	0.01603 (15)
H16A	0.5201	0.6637	0.4430	0.019*
H16B	0.4291	0.5694	0.4279	0.019*
H1N2	0.2826 (9)	0.353 (2)	0.8337 (12)	0.030 (4)*
H2N2	0.3333 (10)	0.203 (2)	0.7873 (13)	0.036 (4)*
H1N4	0.3319 (9)	0.163 (2)	0.4039 (12)	0.027 (3)*
H2N4	0.2840 (9)	0.316 (2)	0.3262 (13)	0.035 (4)*
H1O1	0.3554 (11)	1.070 (2)	0.6062 (14)	0.041 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0314 (3)	0.0187 (3)	0.0169 (3)	0.0107 (3)	0.0047 (2)	0.0004 (2)
O2	0.0258 (3)	0.0157 (3)	0.0157 (3)	0.0051 (2)	0.0006 (2)	−0.0016 (2)
O3	0.0257 (3)	0.0149 (3)	0.0178 (3)	0.0063 (2)	0.0016 (2)	0.0010 (2)
N1	0.0156 (3)	0.0133 (3)	0.0100 (3)	0.0017 (2)	0.0017 (2)	0.0006 (2)
N2	0.0233 (3)	0.0151 (3)	0.0097 (3)	0.0037 (3)	0.0011 (2)	0.0014 (2)
N3	0.0158 (3)	0.0130 (3)	0.0102 (3)	0.0015 (2)	0.0019 (2)	0.0001 (2)
N4	0.0223 (3)	0.0147 (3)	0.0106 (3)	0.0037 (3)	0.0026 (2)	−0.0006 (2)
N5	0.0155 (3)	0.0137 (3)	0.0105 (3)	0.0024 (2)	0.0022 (2)	−0.0002 (2)
C2	0.0131 (3)	0.0128 (3)	0.0106 (3)	−0.0002 (2)	0.0008 (2)	0.0005 (2)
C4	0.0130 (3)	0.0128 (3)	0.0111 (3)	−0.0005 (2)	0.0016 (2)	−0.0003 (2)
C6	0.0122 (3)	0.0135 (3)	0.0102 (3)	0.0006 (2)	0.0014 (2)	0.0001 (2)
C7	0.0132 (3)	0.0143 (4)	0.0115 (3)	0.0019 (3)	0.0023 (2)	0.0002 (3)
C8	0.0170 (3)	0.0172 (4)	0.0121 (3)	0.0024 (3)	0.0010 (2)	−0.0003 (3)
C9	0.0193 (3)	0.0158 (4)	0.0139 (3)	0.0025 (3)	0.0021 (3)	−0.0019 (3)
C10	0.0142 (3)	0.0138 (4)	0.0156 (3)	0.0016 (3)	0.0020 (2)	0.0005 (3)
C11	0.0187 (3)	0.0169 (4)	0.0132 (3)	0.0038 (3)	0.0010 (3)	0.0010 (3)
C12	0.0190 (3)	0.0168 (4)	0.0119 (3)	0.0040 (3)	0.0016 (2)	−0.0002 (3)
C13	0.0247 (4)	0.0187 (4)	0.0202 (4)	0.0055 (3)	0.0001 (3)	0.0037 (3)
C14	0.0149 (3)	0.0127 (4)	0.0173 (3)	0.0007 (3)	0.0012 (2)	−0.0017 (3)
C15	0.0177 (3)	0.0132 (4)	0.0179 (3)	0.0033 (3)	0.0017 (3)	0.0004 (3)
C16	0.0164 (3)	0.0130 (4)	0.0185 (3)	0.0032 (3)	0.0011 (3)	−0.0003 (3)

O1—C14	1.3199 (10)	C7—C8	1.4018 (11)
O1—H1O1	0.952 (17)	C8—C9	1.3851 (12)
O2—C14	1.2249 (10)	C8—H8A	0.9500
O3—C10	1.3595 (10)	C9—C10	1.3991 (11)
O3—C13	1.4314 (11)	C9—H9A	0.9500
N1—C6	1.3377 (10)	C10—C11	1.3942 (12)
N1—C2	1.3587 (10)	C11—C12	1.3944 (12)
N2—C2	1.3337 (10)	C11—H11A	0.9500
N2—H1N2	0.894 (15)	C12—H12A	0.9500
N2—H2N2	0.868 (16)	C13—H13A	0.9800
N3—C4	1.3472 (10)	C13—H13B	0.9800
N3—C2	1.3473 (10)	C13—H13C	0.9800
N4—C4	1.3347 (10)	C14—C15	1.5072 (12)
N4—H1N4	0.903 (15)	C15—C16	1.5226 (12)
N4—H2N4	0.906 (16)	C15—H15A	0.9900
N5—C6	1.3415 (10)	C15—H15B	0.9900
N5—C4	1.3524 (11)	C16—C16i	1.5251 (17)
C6—C7	1.4783 (11)	C16—H16A	0.9900
C7—C12	1.3985 (11)	C16—H16B	0.9900
C14—O1—H1O1	107.1 (10)	O3—C10—C9	115.80 (7)
C10—O3—C13	117.23 (7)	C11—C10—C9	119.73 (8)
C6—N1—C2	114.56 (7)	C10—C11—C12	119.41 (7)
C2—N2—H1N2	119.2 (10)	C10—C11—H11A	120.3
C2—N2—H2N2	122.8 (10)	C12—C11—H11A	120.3
H1N2—N2—H2N2	118.0 (14)	C11—C12—C7	121.49 (7)
C4—N3—C2	115.37 (7)	C11—C12—H12A	119.3
C4—N4—H1N4	118.1 (9)	C7—C12—H12A	119.3
C4—N4—H2N4	117.7 (10)	O3—C13—H13A	109.5
H1N4—N4—H2N4	123.8 (14)	O3—C13—H13B	109.5
C6—N5—C4	115.48 (7)	H13A—C13—H13B	109.5
N2—C2—N3	117.83 (7)	O3—C13—H13C	109.5
N2—C2—N1	117.29 (7)	H13A—C13—H13C	109.5
N3—C2—N1	124.88 (7)	H13B—C13—H13C	109.5
N4—C4—N3	118.09 (7)	O2—C14—O1	123.24 (8)
N4—C4—N5	117.76 (7)	O2—C14—C15	123.73 (7)
N3—C4—N5	124.15 (7)	O1—C14—C15	113.04 (7)
N1—C6—N5	125.52 (7)	C14—C15—C16	114.03 (7)
N1—C6—C7	118.30 (7)	C14—C15—H15A	108.7
N5—C6—C7	116.17 (7)	C16—C15—H15A	108.7
C12—C7—C8	118.16 (8)	C14—C15—H15B	108.7
C12—C7—C6	119.94 (7)	C16—C15—H15B	108.7
C8—C7—C6	121.89 (7)	H15A—C15—H15B	107.6
C9—C8—C7	120.88 (7)	C15—C16—C16i	111.86 (9)
C9—C8—H8A	119.6	C15—C16—H16A	109.2
C7—C8—H8A	119.6	C16i—C16—H16A	109.2
C8—C9—C10	120.26 (7)	C15—C16—H16B	109.2
C8—C9—H9A	119.9	C16i—C16—H16B	109.2
C10—C9—H9A	119.9	H16A—C16—H16B	107.9
O3—C10—C11	124.46 (7)
C4—N3—C2—N2	178.22 (7)	C12—C7—C8—C9	−1.99 (12)
C4—N3—C2—N1	−1.99 (11)	C6—C7—C8—C9	176.85 (7)
C6—N1—C2—N2	−179.18 (7)	C7—C8—C9—C10	−0.16 (12)
C6—N1—C2—N3	1.04 (11)	C13—O3—C10—C11	−4.03 (12)
C2—N3—C4—N4	−178.37 (7)	C13—O3—C10—C9	175.58 (7)
C2—N3—C4—N5	2.48 (11)	C8—C9—C10—O3	−177.20 (7)
C6—N5—C4—N4	178.87 (7)	C8—C9—C10—C11	2.43 (12)
C6—N5—C4—N3	−1.97 (11)	O3—C10—C11—C12	177.11 (8)
C2—N1—C6—N5	−0.45 (12)	C9—C10—C11—C12	−2.49 (12)
C2—N1—C6—C7	−179.26 (7)	C10—C11—C12—C7	0.30 (12)
C4—N5—C6—N1	0.90 (12)	C8—C7—C12—C11	1.92 (12)
C4—N5—C6—C7	179.73 (7)	C6—C7—C12—C11	−176.95 (7)
N1—C6—C7—C12	−168.63 (7)	O2—C14—C15—C16	−4.38 (12)
N5—C6—C7—C12	12.46 (11)	O1—C14—C15—C16	175.24 (7)
N1—C6—C7—C8	12.56 (11)	C14—C15—C16—C16i	−175.20 (8)
N5—C6—C7—C8	−166.36 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···N5ii	0.894 (15)	2.051 (15)	2.9438 (10)	177.7 (14)
N2—H2N2···O2ii	0.868 (16)	2.336 (16)	2.9891 (10)	132.2 (13)
N4—H1N4···O2iii	0.901 (15)	2.021 (15)	2.9142 (11)	170.9 (13)
N4—H2N4···N1iv	0.906 (16)	2.245 (16)	3.1456 (10)	172.5 (14)
O1—H1O1···N3v	0.953 (15)	1.728 (15)	2.6655 (10)	167.5 (15)
C13—H13A···O3vi	0.98	2.53	3.3997 (12)	148
C15—H15A···Cg1	0.99	2.83	3.598	135

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C2/N3/C4/N5/C6 triazine ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯N5i	0.894 (15)	2.051 (15)	2.9438 (10)	177.7 (14)
N2—H2N2⋯O2i	0.868 (16)	2.336 (16)	2.9891 (10)	132.2 (13)
N4—H1N4⋯O2ii	0.901 (15)	2.021 (15)	2.9142 (11)	170.9 (13)
N4—H2N4⋯N1iii	0.906 (16)	2.245 (16)	3.1456 (10)	172.5 (14)
O1—H1O1⋯N3iv	0.953 (15)	1.728 (15)	2.6655 (10)	167.5 (15)
C13—H13A⋯O3v	0.98	2.53	3.3997 (12)	148
C15—H15A⋯Cg1	0.99	2.83	3.598	135

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