6-(4-Meth-oxy-phen-yl)-1,3,5-triazine-2,4-diamine.

In the title compound, C(10)H(11)N(5)O, the triazine ring forms a dihedral angle of 10.37 (4)° with the benzene ring. In the crystal, adjacent mol-ecules are linked by a pair of N-H⋯N hydrogen bonds, forming an inversion dimer with an R(2) (2)(8) ring motif. The dimers are further connected via N-H⋯O and N-H⋯N hydrogen bonds, resulting in a three-dimensional network.

Related literature

For the biological activity of triazine derivatives, see: Bork et al. (2003 ▶). 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

C10H11N5O

M = 217.24

Monoclinic,

a = 7.4340 (2) Å

b = 10.0355 (3) Å

c = 14.6803 (4) Å

β = 114.191 (1)°

V = 999.03 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.73 × 0.49 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.930, T max = 0.985

16310 measured reflections

3611 independent reflections

3112 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.121

S = 1.07

3611 reflections

162 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.26 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/S1600536812038019/is5191sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038019/is5191Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812038019/is5191Isup3.cml

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

C10H11N5O	F(000) = 456
Mr = 217.24	Dx = 1.444 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7910 reflections
a = 7.4340 (2) Å	θ = 2.5–32.5°
b = 10.0355 (3) Å	µ = 0.10 mm−1
c = 14.6803 (4) Å	T = 100 K
β = 114.191 (1)°	Plate, colourless
V = 999.03 (5) Å3	0.73 × 0.49 × 0.15 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3611 independent reflections
Radiation source: fine-focus sealed tube	3112 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 32.6°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.930, Tmax = 0.985	k = −15→14
16310 measured reflections	l = −22→22

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0686P)2 + 0.2052P] where P = (Fo2 + 2Fc2)/3
3611 reflections	(Δ/σ)max < 0.001
162 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.26 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	0.35597 (9)	0.64750 (7)	0.95775 (5)	0.01650 (14)
N1	0.89236 (10)	0.73352 (7)	0.71745 (5)	0.01370 (14)
N2	1.14046 (11)	0.80754 (8)	0.67477 (6)	0.01588 (15)
N3	0.98420 (10)	0.61218 (7)	0.60228 (5)	0.01364 (14)
N4	0.81934 (12)	0.41721 (8)	0.53671 (6)	0.01771 (16)
N5	0.74625 (11)	0.52210 (7)	0.65619 (5)	0.01434 (15)
C2	1.00276 (12)	0.71420 (8)	0.66483 (6)	0.01287 (15)
C4	0.85102 (12)	0.51935 (8)	0.59951 (6)	0.01342 (15)
C6	0.76980 (11)	0.63268 (8)	0.71082 (6)	0.01251 (15)
C7	0.65370 (12)	0.63948 (8)	0.77219 (6)	0.01286 (15)
C8	0.50541 (12)	0.54629 (9)	0.75799 (6)	0.01468 (16)
H8A	0.4749	0.4824	0.7061	0.018*
C9	0.40092 (12)	0.54448 (8)	0.81785 (6)	0.01421 (16)
H9A	0.3015	0.4796	0.8078	0.017*
C10	0.44520 (12)	0.63999 (8)	0.89293 (6)	0.01308 (15)
C11	0.59087 (12)	0.73581 (9)	0.90702 (6)	0.01452 (16)
H11A	0.6182	0.8016	0.9575	0.017*
C12	0.69527 (12)	0.73512 (8)	0.84777 (6)	0.01394 (16)
H12A	0.7954	0.7996	0.8583	0.017*
C13	0.19727 (13)	0.55633 (10)	0.94259 (7)	0.01802 (17)
H13A	0.1488	0.5697	0.9947	0.027*
H13B	0.2448	0.4646	0.9457	0.027*
H13C	0.0900	0.5724	0.8770	0.027*
H2A	1.236 (2)	0.7853 (15)	0.6551 (11)	0.031 (4)*
H2B	1.1747 (19)	0.8611 (14)	0.7264 (10)	0.023 (3)*
H4A	0.882 (2)	0.4077 (15)	0.4965 (11)	0.029 (3)*
H4B	0.739 (2)	0.3525 (15)	0.5360 (11)	0.030 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0177 (3)	0.0169 (3)	0.0189 (3)	−0.0022 (2)	0.0116 (2)	−0.0023 (2)
N1	0.0149 (3)	0.0116 (3)	0.0165 (3)	−0.0003 (2)	0.0083 (2)	−0.0002 (2)
N2	0.0171 (3)	0.0136 (3)	0.0197 (3)	−0.0030 (3)	0.0103 (3)	−0.0022 (3)
N3	0.0151 (3)	0.0123 (3)	0.0149 (3)	−0.0006 (2)	0.0075 (2)	0.0002 (2)
N4	0.0216 (3)	0.0152 (3)	0.0216 (3)	−0.0053 (3)	0.0143 (3)	−0.0051 (3)
N5	0.0163 (3)	0.0121 (3)	0.0174 (3)	−0.0008 (3)	0.0098 (3)	−0.0011 (2)
C2	0.0131 (3)	0.0114 (3)	0.0139 (3)	0.0015 (3)	0.0054 (3)	0.0021 (3)
C4	0.0146 (3)	0.0120 (3)	0.0143 (3)	0.0013 (3)	0.0064 (3)	0.0008 (3)
C6	0.0128 (3)	0.0111 (3)	0.0137 (3)	0.0014 (3)	0.0055 (3)	0.0013 (3)
C7	0.0134 (3)	0.0108 (3)	0.0154 (3)	0.0011 (3)	0.0070 (3)	0.0002 (3)
C8	0.0156 (3)	0.0128 (3)	0.0170 (3)	−0.0004 (3)	0.0081 (3)	−0.0025 (3)
C9	0.0137 (3)	0.0122 (3)	0.0177 (3)	−0.0007 (3)	0.0074 (3)	−0.0007 (3)
C10	0.0130 (3)	0.0128 (3)	0.0145 (3)	0.0020 (3)	0.0066 (3)	0.0012 (3)
C11	0.0159 (3)	0.0133 (4)	0.0154 (3)	−0.0009 (3)	0.0074 (3)	−0.0025 (3)
C12	0.0139 (3)	0.0119 (3)	0.0168 (3)	−0.0003 (3)	0.0069 (3)	−0.0004 (3)
C13	0.0157 (3)	0.0206 (4)	0.0199 (4)	−0.0016 (3)	0.0095 (3)	0.0022 (3)

O1—C10	1.3669 (10)	C6—C7	1.4826 (11)
O1—C13	1.4364 (11)	C7—C8	1.3946 (12)
N1—C6	1.3384 (11)	C7—C12	1.4025 (12)
N1—C2	1.3517 (10)	C8—C9	1.3911 (11)
N2—C2	1.3507 (11)	C8—H8A	0.9500
N2—H2A	0.896 (15)	C9—C10	1.3945 (12)
N2—H2B	0.877 (14)	C9—H9A	0.9500
N3—C2	1.3441 (11)	C10—C11	1.3988 (12)
N3—C4	1.3479 (11)	C11—C12	1.3828 (11)
N4—C4	1.3335 (11)	C11—H11A	0.9500
N4—H4A	0.896 (15)	C12—H12A	0.9500
N4—H4B	0.878 (15)	C13—H13A	0.9800
N5—C6	1.3380 (11)	C13—H13B	0.9800
N5—C4	1.3530 (10)	C13—H13C	0.9800
C10—O1—C13	117.33 (7)	C9—C8—C7	121.75 (8)
C6—N1—C2	113.87 (7)	C9—C8—H8A	119.1
C2—N2—H2A	117.2 (10)	C7—C8—H8A	119.1
C2—N2—H2B	117.2 (9)	C8—C9—C10	118.57 (8)
H2A—N2—H2B	116.3 (13)	C8—C9—H9A	120.7
C2—N3—C4	114.56 (7)	C10—C9—H9A	120.7
C4—N4—H4A	123.0 (10)	O1—C10—C9	124.29 (7)
C4—N4—H4B	120.3 (9)	O1—C10—C11	115.23 (7)
H4A—N4—H4B	116.6 (13)	C9—C10—C11	120.47 (7)
C6—N5—C4	114.75 (7)	C12—C11—C10	120.24 (8)
N3—C2—N2	117.59 (7)	C12—C11—H11A	119.9
N3—C2—N1	125.68 (7)	C10—C11—H11A	119.9
N2—C2—N1	116.72 (7)	C11—C12—C7	120.17 (8)
N4—C4—N3	118.14 (7)	C11—C12—H12A	119.9
N4—C4—N5	117.24 (7)	C7—C12—H12A	119.9
N3—C4—N5	124.62 (8)	O1—C13—H13A	109.5
N5—C6—N1	126.06 (7)	O1—C13—H13B	109.5
N5—C6—C7	115.89 (7)	H13A—C13—H13B	109.5
N1—C6—C7	118.00 (7)	O1—C13—H13C	109.5
C8—C7—C12	118.78 (7)	H13A—C13—H13C	109.5
C8—C7—C6	119.98 (7)	H13B—C13—H13C	109.5
C12—C7—C6	121.18 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N5i	0.878 (14)	2.258 (14)	3.1291 (11)	172.1 (12)
N4—H4A···N3ii	0.894 (16)	2.077 (16)	2.9708 (12)	177.4 (14)
N4—H4B···O1iii	0.879 (16)	2.189 (15)	3.0196 (11)	157.3 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯N5i	0.878 (14)	2.258 (14)	3.1291 (11)	172.1 (12)
N4—H4A⋯N3ii	0.894 (16)	2.077 (16)	2.9708 (12)	177.4 (14)
N4—H4B⋯O1iii	0.879 (16)	2.189 (15)	3.0196 (11)	157.3 (14)

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