6-(4-Methyl-phen-yl)-1,3,5-triazine-2,4-di-amine-4-methyl-benzoic acid (1/1).

The 4-methyl-benzoic acid mol-ecule of the title adduct, C10H11N5·C8H8O2, is approximately planar with a dihedral angle of 6.3 (2)° between the carb-oxy-lic acid group and the benzene ring. In the triazine mol-ecule, the plane of the triazine ring makes a dihedral angle of 29.2 (2)° with that of the adjacent benzene ring. In the crystal, the acid and base mol-ecules are linked via N-H⋯O and O-H⋯N hydrogen bonds with an R 2 (2)(8) motif, and the acid-base pairs are further connected via N-H⋯N hydrogen bonds with R 2 (2)(8) motifs, forming a supra-molecular ribbon along [101]. Between the tapes, a weak C-H⋯π inter-action is observed.

Related literature

The background to this study has been described in the preceding paper, see: Thanigaimani et al. (2013 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C10H11N5·C8H8O2

M = 337.38

Monoclinic,

a = 11.1271 (3) Å

b = 20.9492 (6) Å

c = 7.4189 (2) Å

β = 101.321 (2)°

V = 1695.73 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.40 × 0.40 × 0.20 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.965, T max = 0.982

8715 measured reflections

1932 independent reflections

1811 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.135

S = 1.19

1932 reflections

244 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.27 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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813013895/is5272sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013895/is5272Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813013895/is5272Isup3.cml

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

C10H11N5·C8H8O2	F(000) = 712
Mr = 337.38	Dx = 1.322 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 6815 reflections
a = 11.1271 (3) Å	θ = 3.2–33.7°
b = 20.9492 (6) Å	µ = 0.09 mm−1
c = 7.4189 (2) Å	T = 100 K
β = 101.321 (2)°	Plate, colourless
V = 1695.73 (8) Å3	0.40 × 0.40 × 0.20 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	1932 independent reflections
Radiation source: fine-focus sealed tube	1811 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
Tmin = 0.965, Tmax = 0.982	k = −27→27
8715 measured reflections	l = −9→7

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	w = 1/[σ2(Fo2) + (0.0311P)2 + 4.4301P] where P = (Fo2 + 2Fc2)/3
1932 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.27 e Å−3
3 restraints	Δρmin = −0.27 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
N1	0.4994 (3)	0.25996 (17)	0.3556 (5)	0.0165 (8)
N2	0.3884 (4)	0.16295 (15)	0.2802 (6)	0.0170 (7)
N3	0.2919 (3)	0.26326 (16)	0.1933 (6)	0.0164 (7)
N4	0.5874 (3)	0.16186 (18)	0.4348 (5)	0.0200 (8)
H1N4	0.581 (5)	0.116 (3)	0.447 (8)	0.030*
H2N4	0.646 (3)	0.183 (2)	0.496 (7)	0.030*
N5	0.1876 (3)	0.16862 (19)	0.1268 (6)	0.0235 (9)
H1N5	0.126 (5)	0.188 (3)	0.049 (9)	0.035*
H2N5	0.188 (5)	0.126 (3)	0.120 (8)	0.035*
C1	0.4899 (4)	0.19523 (19)	0.3563 (6)	0.0156 (8)
C2	0.2928 (4)	0.19889 (19)	0.2015 (6)	0.0169 (8)
C3	0.3982 (4)	0.29042 (16)	0.2738 (7)	0.0150 (7)
C4	0.4034 (4)	0.36131 (17)	0.2713 (7)	0.0166 (8)
C5	0.2976 (4)	0.3973 (2)	0.2713 (6)	0.0189 (9)
H5A	0.2217	0.3762	0.2690	0.023*
C6	0.3023 (4)	0.4632 (2)	0.2746 (7)	0.0228 (10)
H6A	0.2296	0.4870	0.2744	0.027*
C7	0.4126 (4)	0.49501 (18)	0.2781 (7)	0.0216 (9)
C8	0.5170 (4)	0.4596 (2)	0.2779 (7)	0.0236 (10)
H8A	0.5926	0.4809	0.2798	0.028*
C9	0.5136 (4)	0.39311 (19)	0.2749 (6)	0.0187 (9)
H9A	0.5865	0.3695	0.2753	0.022*
C10	0.4170 (5)	0.5672 (2)	0.2789 (8)	0.0306 (11)
H10A	0.4988	0.5814	0.3396	0.046*
H10B	0.3558	0.5838	0.3455	0.046*
H10C	0.3991	0.5830	0.1521	0.046*
O1	0.5390 (3)	0.02412 (14)	0.4355 (5)	0.0245 (7)
O2	0.3551 (3)	0.03627 (15)	0.2514 (5)	0.0248 (7)
C11	0.3135 (5)	−0.1599 (2)	0.1798 (7)	0.0298 (12)
H11A	0.2450	−0.1770	0.0970	0.036*
C12	0.3269 (4)	−0.0939 (2)	0.1967 (7)	0.0253 (10)
H12A	0.2683	−0.0662	0.1258	0.030*
C13	0.4271 (4)	−0.0689 (2)	0.3187 (6)	0.0201 (10)
C14	0.5126 (5)	−0.1101 (2)	0.4226 (7)	0.0268 (10)
H14A	0.5807	−0.0934	0.5069	0.032*
C15	0.4970 (5)	−0.1754 (2)	0.4014 (7)	0.0305 (12)
H15A	0.5557	−0.2033	0.4711	0.037*
C16	0.3977 (6)	−0.20104 (19)	0.2808 (10)	0.0338 (12)
C17	0.3816 (7)	−0.2731 (2)	0.2623 (12)	0.0459 (16)
H17A	0.3450	−0.2838	0.1348	0.069*
H17B	0.3278	−0.2879	0.3437	0.069*
H17C	0.4617	−0.2939	0.2967	0.069*
C18	0.4468 (4)	0.0016 (2)	0.3420 (6)	0.0202 (9)
H1O2	0.370 (6)	0.072 (3)	0.253 (9)	0.038 (16)*

	U11	U22	U33	U12	U13	U23
N1	0.0140 (17)	0.0145 (17)	0.0190 (18)	−0.0002 (14)	−0.0018 (15)	−0.0001 (15)
N2	0.0159 (16)	0.0136 (14)	0.0195 (15)	0.0007 (15)	−0.0012 (13)	−0.0001 (17)
N3	0.0125 (15)	0.0127 (17)	0.0224 (18)	0.0006 (14)	−0.0002 (14)	0.0021 (15)
N4	0.0155 (17)	0.0140 (17)	0.027 (2)	−0.0007 (14)	−0.0055 (15)	−0.0017 (15)
N5	0.0146 (18)	0.0144 (19)	0.037 (2)	−0.0030 (14)	−0.0063 (17)	0.0027 (16)
C1	0.0154 (18)	0.0128 (18)	0.0183 (19)	0.0004 (16)	0.0024 (16)	0.0000 (17)
C2	0.0151 (18)	0.017 (2)	0.018 (2)	−0.0021 (17)	0.0015 (16)	0.0000 (18)
C3	0.0138 (17)	0.0147 (16)	0.0168 (17)	0.0002 (17)	0.0041 (14)	−0.0008 (19)
C4	0.0211 (19)	0.0130 (16)	0.0141 (18)	0.0003 (18)	−0.0009 (15)	−0.0020 (19)
C5	0.0129 (19)	0.020 (2)	0.021 (2)	−0.0008 (16)	−0.0049 (16)	−0.0015 (17)
C6	0.022 (2)	0.019 (2)	0.024 (2)	0.0083 (18)	−0.0040 (18)	−0.0040 (18)
C7	0.032 (2)	0.0132 (17)	0.0169 (18)	−0.0022 (19)	−0.0026 (18)	0.000 (2)
C8	0.025 (2)	0.017 (2)	0.027 (2)	−0.0084 (17)	0.0001 (19)	0.0010 (18)
C9	0.018 (2)	0.0148 (19)	0.021 (2)	−0.0005 (16)	−0.0018 (17)	−0.0002 (17)
C10	0.047 (3)	0.0130 (18)	0.030 (2)	0.002 (2)	0.003 (2)	0.001 (2)
O1	0.0219 (16)	0.0158 (13)	0.0323 (18)	−0.0005 (13)	−0.0035 (13)	0.0004 (14)
O2	0.0205 (15)	0.0135 (14)	0.037 (2)	−0.0021 (12)	−0.0022 (14)	0.0019 (14)
C11	0.031 (3)	0.024 (2)	0.039 (3)	−0.013 (2)	0.019 (2)	−0.015 (2)
C12	0.025 (2)	0.020 (2)	0.034 (3)	0.0007 (18)	0.014 (2)	−0.007 (2)
C13	0.019 (2)	0.0170 (19)	0.028 (3)	−0.0016 (16)	0.0145 (19)	−0.0006 (17)
C14	0.032 (3)	0.019 (2)	0.033 (3)	0.0043 (19)	0.015 (2)	0.003 (2)
C15	0.041 (3)	0.020 (2)	0.036 (3)	0.008 (2)	0.020 (2)	0.009 (2)
C16	0.052 (3)	0.0146 (19)	0.045 (3)	−0.001 (2)	0.034 (2)	−0.005 (3)
C17	0.074 (4)	0.017 (2)	0.058 (4)	−0.008 (3)	0.041 (3)	−0.005 (3)
C18	0.019 (2)	0.0158 (19)	0.026 (2)	0.0017 (17)	0.0062 (18)	−0.002 (2)

N1—C3	1.333 (5)	C9—H9A	0.9500
N1—C1	1.360 (5)	C10—H10A	0.9800
N2—C2	1.340 (5)	C10—H10B	0.9800
N2—C1	1.342 (6)	C10—H10C	0.9800
N3—C3	1.342 (5)	O1—C18	1.215 (5)
N3—C2	1.350 (5)	O2—C18	1.324 (5)
N4—C1	1.326 (5)	O2—H1O2	0.77 (6)
N4—H1N4	0.97 (6)	C11—C16	1.380 (8)
N4—H2N4	0.849 (11)	C11—C12	1.395 (6)
N5—C2	1.351 (5)	C11—H11A	0.9500
N5—H1N5	0.90 (6)	C12—C13	1.393 (6)
N5—H2N5	0.89 (6)	C12—H12A	0.9500
C3—C4	1.487 (5)	C13—C14	1.398 (6)
C4—C9	1.390 (6)	C13—C18	1.498 (6)
C4—C5	1.398 (6)	C14—C15	1.384 (6)
C5—C6	1.382 (6)	C14—H14A	0.9500
C5—H5A	0.9500	C15—C16	1.386 (8)
C6—C7	1.392 (7)	C15—H15A	0.9500
C6—H6A	0.9500	C16—C17	1.523 (6)
C7—C8	1.378 (6)	C17—H17A	0.9800
C7—C10	1.512 (5)	C17—H17B	0.9800
C8—C9	1.394 (6)	C17—H17C	0.9800
C8—H8A	0.9500
C3—N1—C1	114.8 (3)	C8—C9—H9A	120.0
C2—N2—C1	115.5 (3)	C7—C10—H10A	109.5
C3—N3—C2	113.9 (3)	C7—C10—H10B	109.5
C1—N4—H1N4	120 (3)	H10A—C10—H10B	109.5
C1—N4—H2N4	116 (4)	C7—C10—H10C	109.5
H1N4—N4—H2N4	122 (5)	H10A—C10—H10C	109.5
C2—N5—H1N5	123 (4)	H10B—C10—H10C	109.5
C2—N5—H2N5	119 (4)	C18—O2—H1O2	113 (5)
H1N5—N5—H2N5	115 (5)	C16—C11—C12	121.4 (5)
N4—C1—N2	117.9 (4)	C16—C11—H11A	119.3
N4—C1—N1	118.0 (4)	C12—C11—H11A	119.3
N2—C1—N1	124.1 (4)	C13—C12—C11	119.2 (5)
N2—C2—N3	125.4 (4)	C13—C12—H12A	120.4
N2—C2—N5	117.7 (4)	C11—C12—H12A	120.4
N3—C2—N5	116.9 (4)	C12—C13—C14	119.9 (4)
N1—C3—N3	126.3 (3)	C12—C13—C18	121.7 (4)
N1—C3—C4	116.9 (4)	C14—C13—C18	118.5 (4)
N3—C3—C4	116.8 (3)	C15—C14—C13	119.4 (5)
C9—C4—C5	118.8 (3)	C15—C14—H14A	120.3
C9—C4—C3	121.0 (4)	C13—C14—H14A	120.3
C5—C4—C3	120.2 (4)	C14—C15—C16	121.5 (5)
C6—C5—C4	120.6 (4)	C14—C15—H15A	119.2
C6—C5—H5A	119.7	C16—C15—H15A	119.2
C4—C5—H5A	119.7	C11—C16—C15	118.6 (4)
C5—C6—C7	120.6 (4)	C11—C16—C17	121.0 (6)
C5—C6—H6A	119.7	C15—C16—C17	120.5 (6)
C7—C6—H6A	119.7	C16—C17—H17A	109.5
C8—C7—C6	118.9 (4)	C16—C17—H17B	109.5
C8—C7—C10	120.7 (4)	H17A—C17—H17B	109.5
C6—C7—C10	120.4 (4)	C16—C17—H17C	109.5
C7—C8—C9	121.2 (4)	H17A—C17—H17C	109.5
C7—C8—H8A	119.4	H17B—C17—H17C	109.5
C9—C8—H8A	119.4	O1—C18—O2	123.8 (4)
C4—C9—C8	120.0 (4)	O1—C18—C13	122.5 (4)
C4—C9—H9A	120.0	O2—C18—C13	113.7 (4)
C2—N2—C1—N4	−179.5 (4)	C5—C6—C7—C10	179.1 (5)
C2—N2—C1—N1	−0.5 (7)	C6—C7—C8—C9	−0.2 (8)
C3—N1—C1—N4	179.7 (4)	C10—C7—C8—C9	−179.2 (4)
C3—N1—C1—N2	0.7 (7)	C5—C4—C9—C8	−0.2 (7)
C1—N2—C2—N3	0.3 (7)	C3—C4—C9—C8	−178.1 (4)
C1—N2—C2—N5	−178.5 (4)	C7—C8—C9—C4	0.3 (7)
C3—N3—C2—N2	−0.3 (7)	C16—C11—C12—C13	−0.2 (7)
C3—N3—C2—N5	178.5 (4)	C11—C12—C13—C14	−0.1 (7)
C1—N1—C3—N3	−0.7 (8)	C11—C12—C13—C18	179.6 (4)
C1—N1—C3—C4	179.3 (4)	C12—C13—C14—C15	0.6 (7)
C2—N3—C3—N1	0.5 (8)	C18—C13—C14—C15	−179.2 (5)
C2—N3—C3—C4	−179.5 (4)	C13—C14—C15—C16	−0.7 (8)
N1—C3—C4—C9	28.0 (7)	C12—C11—C16—C15	0.2 (8)
N3—C3—C4—C9	−152.0 (5)	C12—C11—C16—C17	179.5 (5)
N1—C3—C4—C5	−149.9 (5)	C14—C15—C16—C11	0.3 (9)
N3—C3—C4—C5	30.1 (7)	C14—C15—C16—C17	−179.0 (6)
C9—C4—C5—C6	0.1 (7)	C12—C13—C18—O1	−173.4 (4)
C3—C4—C5—C6	178.0 (4)	C14—C13—C18—O1	6.4 (7)
C4—C5—C6—C7	−0.1 (7)	C12—C13—C18—O2	6.4 (6)
C5—C6—C7—C8	0.1 (8)	C14—C13—C18—O2	−173.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N2	0.77 (6)	1.92 (6)	2.682 (4)	171 (6)
N4—H1N4···O1	0.97 (6)	1.98 (6)	2.936 (5)	169 (6)
N4—H2N4···N3i	0.84 (4)	2.26 (4)	3.099 (5)	172 (4)
N5—H1N5···N1ii	0.90 (6)	2.11 (6)	3.003 (5)	173 (5)
C10—H10C···Cg2iii	0.98	2.83	3.723 (6)	152

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C4–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯N2	0.77 (6)	1.92 (6)	2.682 (4)	171 (6)
N4—H1N4⋯O1	0.97 (6)	1.98 (6)	2.936 (5)	169 (6)
N4—H2N4⋯N3i	0.84 (4)	2.26 (4)	3.099 (5)	172 (4)
N5—H1N5⋯N1ii	0.90 (6)	2.11 (6)	3.003 (5)	173 (5)
C10—H10C⋯Cg2iii	0.98	2.83	3.723 (6)	152

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