N-(3-Methyl-phen-yl)quinoxalin-2-amine monohydrate.

The quinoxaline system in the title hydrate, C(15)H(13)N(3)·H(2)O, is roughly planar, the r.m.s. deviation for the 18 non-H atoms being 0.188 Å; this conformation features a short intra-molecular C-H⋯N(pyrazine) inter-action. In the crystal, the amine H atom forms an N-H⋯O hydrogen bond to the water mol-ecule, which in turn forms two O-H⋯N hydrogen bonds to the pyrazine N atoms of different organic mol-ecules. These inter-actions lead to supra-molecular arrays in the bc plane that are two mol-ecules thick; additional π-π inter-actions stabilize the layers [ring centroid-centroid distance = 3.5923 (7) Å]. The layers stack along the a-axis direction via C-H⋯π contacts.

Related literature

For a related structure, see: Fairuz et al. (2010 ▶). For background to the fluorescence properties of compounds related to the title compound, see: Kawai et al. (2001 ▶); Abdullah (2005 ▶).

Experimental

Crystal data

C15H13N3·H2O

M = 253.30

Monoclinic,

a = 10.9002 (8) Å

b = 11.1048 (8) Å

c = 11.1715 (8) Å

β = 106.780 (1)°

V = 1294.67 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.30 × 0.20 × 0.05 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.942, T max = 1.000

12521 measured reflections

3100 independent reflections

2608 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.110

S = 1.02

3100 reflections

185 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 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: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810031260/hb5601sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031260/hb5601Isup2.hkl

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

C15H13N3·H2O	F(000) = 536
Mr = 253.30	Dx = 1.299 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4286 reflections
a = 10.9002 (8) Å	θ = 2.7–28.1°
b = 11.1048 (8) Å	µ = 0.08 mm−1
c = 11.1715 (8) Å	T = 100 K
β = 106.780 (1)°	Prism, colourless
V = 1294.67 (16) Å3	0.30 × 0.20 × 0.05 mm
Z = 4

Bruker SMART APEX CCD diffractometer	3100 independent reflections
Radiation source: fine-focus sealed tube	2608 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.942, Tmax = 1.000	k = −14→14
12521 measured reflections	l = −13→14

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) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0605P)2 + 0.3508P] where P = (Fo2 + 2Fc2)/3
3100 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.24 e Å−3
3 restraints	Δρmin = −0.27 e Å−3

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
O1W	0.13500 (8)	0.90644 (8)	0.33421 (8)	0.0223 (2)
N1	0.23584 (9)	0.74212 (8)	0.54040 (9)	0.0164 (2)
N2	0.22297 (8)	0.54565 (8)	0.61373 (8)	0.0155 (2)
N3	0.09733 (9)	0.48107 (8)	0.36216 (9)	0.0173 (2)
C1	0.31138 (10)	0.80081 (10)	0.64828 (10)	0.0160 (2)
C2	0.32032 (11)	0.92624 (10)	0.63975 (11)	0.0197 (2)
H2	0.2719	0.9673	0.5668	0.024*
C3	0.40005 (11)	0.99008 (11)	0.73821 (12)	0.0229 (3)
H3	0.4062	1.0751	0.7323	0.027*
C4	0.47106 (11)	0.93112 (11)	0.84546 (11)	0.0221 (3)
H4	0.5267	0.9758	0.9117	0.027*
C5	0.46125 (10)	0.80690 (11)	0.85650 (10)	0.0190 (2)
C6	0.38116 (10)	0.74173 (10)	0.75738 (10)	0.0171 (2)
H6	0.3741	0.6569	0.7641	0.021*
C7	0.53811 (11)	0.74244 (12)	0.97319 (11)	0.0241 (3)
H7A	0.5289	0.7848	1.0471	0.036*
H7B	0.6286	0.7410	0.9755	0.036*
H7C	0.5066	0.6597	0.9727	0.036*
C8	0.20156 (10)	0.62408 (10)	0.52164 (10)	0.0148 (2)
C9	0.13809 (10)	0.58960 (10)	0.39371 (10)	0.0165 (2)
H9	0.1258	0.6490	0.3301	0.020*
C10	0.11971 (10)	0.39634 (10)	0.45706 (10)	0.0158 (2)
C11	0.07801 (10)	0.27676 (10)	0.42863 (11)	0.0197 (2)
H11A	0.0344	0.2549	0.3449	0.024*
C12	0.10028 (11)	0.19203 (10)	0.52154 (12)	0.0221 (3)
H12A	0.0720	0.1115	0.5021	0.027*
C13	0.16493 (11)	0.22376 (10)	0.64566 (11)	0.0216 (2)
H13	0.1804	0.1643	0.7095	0.026*
C14	0.20597 (11)	0.34018 (10)	0.67553 (11)	0.0194 (2)
H14	0.2495	0.3606	0.7597	0.023*
C15	0.18364 (10)	0.42907 (10)	0.58167 (10)	0.0155 (2)
H1n	0.2046 (14)	0.7886 (12)	0.4763 (11)	0.028 (4)*
H1w	0.1780 (15)	0.9131 (16)	0.2821 (14)	0.042 (5)*
H2w	0.0595 (11)	0.9256 (17)	0.2944 (16)	0.052 (5)*

	U11	U22	U33	U12	U13	U23
O1W	0.0230 (4)	0.0262 (5)	0.0170 (4)	0.0023 (3)	0.0046 (3)	0.0060 (3)
N1	0.0191 (4)	0.0137 (4)	0.0140 (4)	−0.0006 (3)	0.0010 (3)	0.0017 (3)
N2	0.0175 (4)	0.0142 (4)	0.0144 (4)	0.0003 (3)	0.0040 (3)	−0.0004 (3)
N3	0.0180 (4)	0.0180 (5)	0.0153 (5)	−0.0011 (3)	0.0042 (3)	−0.0015 (4)
C1	0.0149 (5)	0.0165 (5)	0.0170 (5)	−0.0009 (4)	0.0053 (4)	−0.0021 (4)
C2	0.0209 (5)	0.0169 (5)	0.0212 (6)	−0.0005 (4)	0.0059 (4)	−0.0002 (4)
C3	0.0238 (6)	0.0177 (5)	0.0275 (6)	−0.0040 (4)	0.0080 (5)	−0.0048 (5)
C4	0.0191 (5)	0.0254 (6)	0.0218 (6)	−0.0052 (4)	0.0058 (4)	−0.0082 (5)
C5	0.0159 (5)	0.0253 (6)	0.0162 (5)	−0.0014 (4)	0.0056 (4)	−0.0022 (4)
C6	0.0167 (5)	0.0178 (5)	0.0171 (5)	−0.0012 (4)	0.0052 (4)	−0.0004 (4)
C7	0.0211 (6)	0.0328 (7)	0.0165 (6)	−0.0019 (5)	0.0022 (4)	−0.0013 (5)
C8	0.0135 (5)	0.0152 (5)	0.0156 (5)	0.0008 (4)	0.0039 (4)	−0.0011 (4)
C9	0.0175 (5)	0.0169 (5)	0.0145 (5)	0.0000 (4)	0.0034 (4)	0.0016 (4)
C10	0.0149 (5)	0.0158 (5)	0.0175 (5)	0.0004 (4)	0.0061 (4)	−0.0007 (4)
C11	0.0192 (5)	0.0181 (5)	0.0223 (6)	−0.0024 (4)	0.0068 (4)	−0.0044 (4)
C12	0.0240 (6)	0.0146 (5)	0.0305 (6)	−0.0022 (4)	0.0120 (5)	−0.0021 (5)
C13	0.0265 (6)	0.0166 (5)	0.0248 (6)	0.0028 (4)	0.0125 (5)	0.0049 (4)
C14	0.0234 (5)	0.0178 (5)	0.0182 (5)	0.0025 (4)	0.0080 (4)	0.0007 (4)
C15	0.0161 (5)	0.0150 (5)	0.0167 (5)	0.0009 (4)	0.0065 (4)	−0.0006 (4)

O1W—H1w	0.849 (9)	C5—C7	1.5110 (16)
O1W—H2w	0.842 (9)	C6—H6	0.9500
N1—C8	1.3625 (14)	C7—H7A	0.9800
N1—C1	1.4080 (13)	C7—H7B	0.9800
N1—H1n	0.869 (9)	C7—H7C	0.9800
N2—C8	1.3164 (14)	C8—C9	1.4480 (15)
N2—C15	1.3781 (14)	C9—H9	0.9500
N3—C9	1.2977 (14)	C10—C11	1.4098 (15)
N3—C10	1.3855 (14)	C10—C15	1.4126 (15)
C1—C6	1.3998 (15)	C11—C12	1.3697 (17)
C1—C2	1.4015 (15)	C11—H11A	0.9500
C2—C3	1.3840 (16)	C12—C13	1.4069 (17)
C2—H2	0.9500	C12—H12A	0.9500
C3—C4	1.3885 (17)	C13—C14	1.3772 (16)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.3918 (17)	C14—C15	1.4092 (15)
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.3978 (15)
H1w—O1W—H2w	105.3 (18)	C5—C7—H7C	109.5
C8—N1—C1	130.07 (9)	H7A—C7—H7C	109.5
C8—N1—H1n	114.8 (10)	H7B—C7—H7C	109.5
C1—N1—H1n	115.1 (10)	N2—C8—N1	122.51 (10)
C8—N2—C15	116.54 (9)	N2—C8—C9	121.52 (10)
C9—N3—C10	116.87 (9)	N1—C8—C9	115.97 (9)
C6—C1—C2	119.61 (10)	N3—C9—C8	122.84 (10)
C6—C1—N1	124.39 (10)	N3—C9—H9	118.6
C2—C1—N1	115.90 (10)	C8—C9—H9	118.6
C3—C2—C1	119.67 (11)	N3—C10—C11	119.55 (10)
C3—C2—H2	120.2	N3—C10—C15	120.48 (10)
C1—C2—H2	120.2	C11—C10—C15	119.98 (10)
C2—C3—C4	120.66 (11)	C12—C11—C10	120.08 (11)
C2—C3—H3	119.7	C12—C11—H11A	120.0
C4—C3—H3	119.7	C10—C11—H11A	120.0
C3—C4—C5	120.39 (10)	C11—C12—C13	120.24 (10)
C3—C4—H4	119.8	C11—C12—H12A	119.9
C5—C4—H4	119.8	C13—C12—H12A	119.9
C4—C5—C6	119.30 (10)	C14—C13—C12	120.61 (11)
C4—C5—C7	120.55 (10)	C14—C13—H13	119.7
C6—C5—C7	120.14 (11)	C12—C13—H13	119.7
C5—C6—C1	120.34 (10)	C13—C14—C15	120.20 (11)
C5—C6—H6	119.8	C13—C14—H14	119.9
C1—C6—H6	119.8	C15—C14—H14	119.9
C5—C7—H7A	109.5	N2—C15—C14	119.39 (10)
C5—C7—H7B	109.5	N2—C15—C10	121.72 (10)
H7A—C7—H7B	109.5	C14—C15—C10	118.89 (10)
C8—N1—C1—C6	8.48 (18)	N2—C8—C9—N3	0.87 (17)
C8—N1—C1—C2	−175.06 (11)	N1—C8—C9—N3	−178.34 (10)
C6—C1—C2—C3	1.34 (16)	C9—N3—C10—C11	−179.84 (10)
N1—C1—C2—C3	−175.31 (10)	C9—N3—C10—C15	0.27 (15)
C1—C2—C3—C4	−0.14 (17)	N3—C10—C11—C12	179.60 (10)
C2—C3—C4—C5	−1.21 (18)	C15—C10—C11—C12	−0.51 (16)
C3—C4—C5—C6	1.34 (17)	C10—C11—C12—C13	−0.07 (17)
C3—C4—C5—C7	−179.84 (10)	C11—C12—C13—C14	0.36 (18)
C4—C5—C6—C1	−0.13 (16)	C12—C13—C14—C15	−0.06 (17)
C7—C5—C6—C1	−178.95 (10)	C8—N2—C15—C14	178.78 (10)
C2—C1—C6—C5	−1.20 (16)	C8—N2—C15—C10	−2.12 (15)
N1—C1—C6—C5	175.14 (10)	C13—C14—C15—N2	178.62 (10)
C15—N2—C8—N1	−179.88 (9)	C13—C14—C15—C10	−0.51 (16)
C15—N2—C8—C9	0.96 (15)	N3—C10—C15—N2	1.58 (16)
C1—N1—C8—N2	9.51 (18)	C11—C10—C15—N2	−178.32 (10)
C1—N1—C8—C9	−171.29 (10)	N3—C10—C15—C14	−179.31 (10)
C10—N3—C9—C8	−1.45 (16)	C11—C10—C15—C14	0.79 (16)

Cg1 is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···N2	0.95	2.34	2.9482 (14)	122
N1—H1n···O1w	0.87 (1)	2.03 (1)	2.8951 (12)	176.(2)
O1w—H1w···N2i	0.85 (1)	2.13 (1)	2.9382 (13)	160.(2)
O1w—H2w···N3ii	0.84 (1)	2.15 (1)	2.9504 (12)	158.(2)
C7—H7b···Cg1iii	0.98	2.71	3.6532 (14)	161

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯N2	0.95	2.34	2.9482 (14)	122
N1—H1n⋯O1w	0.87 (1)	2.03 (1)	2.8951 (12)	176 (2)
O1w—H1w⋯N2i	0.85 (1)	2.13 (1)	2.9382 (13)	160 (2)
O1w—H2w⋯N3ii	0.84 (1)	2.15 (1)	2.9504 (12)	158 (2)
C7—H7b⋯Cg1iii	0.98	2.71	3.6532 (14)	161

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