2-[(2-Hy-droxy-benz-yl)amino]-pyrazinium perchlorate-2-[(pyrazin-2-yl-amino)-meth-yl]phenol (1/1).

In the crystal structure of the title co-crystal, C(11)H(12)N(3)O(+)·ClO(4) (-)·C(11)H(11)N(3)O, the perchlorate ion is disordered about a twofold rotation axis with the Cl atom located on the twofold rotation axis; the 2-[(2-hy-droxy-benz-yl)amino]-pyrazinium cation and the neutral 2-[(pyrazin-2-yl-amino)-meth-yl]phenol mol-ecule are disordered about the rotation axis in a 1:1 ratio. These two are connected by a pyrazine-pyrazine N(1)-H⋯N(4) hydrogen bond. The cation, whose two aromatic rings are twisted along the -CH(2)-NH- bond by 76.8 (1)°, is a hydrogen-bond donor to the perchlorate ion through the N atom of this link.

Related literature

For 2-{[(pyrazin-2-yl)amino]­meth­yl}phenol, see: Gao & Ng (2012 ▶).

Experimental

Crystal data

C11H12N3O+·ClO4 −·C11H11N3O

M = 502.91

Monoclinic,

a = 19.3402 (14) Å

b = 5.9467 (3) Å

c = 11.1761 (9) Å

β = 116.263 (10)°

V = 1152.68 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 295 K

0.24 × 0.21 × 0.18 mm

Data collection

Agilent Technologies Excalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.950, T max = 0.962

4085 measured reflections

2272 independent reflections

1859 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.116

S = 1.02

2272 reflections

188 parameters

49 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.29 e Å−3

Absolute structure: Flack (1983 ▶), 970 Friedel pairs

Flack parameter: 0.08 (12)

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812031558/xu5583sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031558/xu5583Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812031558/xu5583Isup3.cml

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

C11H12N3O+·ClO4−·C11H11N3O	F(000) = 524
Mr = 502.91	Dx = 1.449 Mg m−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 1220 reflections
a = 19.3402 (14) Å	θ = 3.6–26.3°
b = 5.9467 (3) Å	µ = 0.22 mm−1
c = 11.1761 (9) Å	T = 295 K
β = 116.263 (10)°	Prism, faint yellow
V = 1152.68 (16) Å3	0.24 × 0.21 × 0.18 mm
Z = 2

Agilent Technologies Excalibur Eos diffractometer	2272 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1859 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
Detector resolution: 16.1954 pixels mm-1	θmax = 26.4°, θmin = 3.6°
ω scan	h = −24→18
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −7→6
Tmin = 0.950, Tmax = 0.962	l = −13→13
4085 measured reflections

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)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.0572P)2 + 0.4309P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2272 reflections	Δρmax = 0.25 e Å−3
188 parameters	Δρmin = −0.29 e Å−3
49 restraints	Absolute structure: Flack (1983), 970 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.08 (12)

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.5000	0.4267 (2)	0.5000	0.0579 (4)
O1	0.69568 (12)	0.7165 (4)	0.1561 (3)	0.0532 (6)
H1	0.7398 (12)	0.706 (9)	0.160 (4)	0.096 (16)*
O2	0.4621 (4)	0.4483 (13)	0.3574 (4)	0.097 (2)	0.50
O3	0.5616 (4)	0.5734 (14)	0.5459 (9)	0.157 (4)	0.50
O4	0.5237 (5)	0.2039 (9)	0.5269 (9)	0.139 (4)	0.50
O5	0.4483 (5)	0.4823 (15)	0.5488 (10)	0.133 (4)	0.50
N1	0.33389 (14)	1.1417 (5)	0.1364 (3)	0.0477 (7)
N2	0.45243 (14)	1.0855 (4)	0.0644 (2)	0.0356 (6)
H2	0.489 (3)	1.095 (11)	0.037 (6)	0.043*	0.50
N3	0.50166 (16)	0.7989 (5)	0.2224 (3)	0.0521 (8)
H3	0.493 (2)	0.719 (7)	0.280 (3)	0.077 (13)*
C1	0.44928 (15)	0.9564 (5)	0.1601 (3)	0.0364 (7)
C2	0.38666 (17)	0.9909 (6)	0.1934 (3)	0.0463 (8)
H2A	0.3837	0.9008	0.2590	0.056*
C3	0.34042 (18)	1.2745 (6)	0.0433 (3)	0.0494 (9)
H3A	0.3046	1.3885	0.0035	0.059*
C4	0.39772 (16)	1.2451 (6)	0.0069 (3)	0.0432 (8)
H4	0.3996	1.3364	−0.0592	0.052*
C6	0.56937 (16)	0.7511 (6)	0.2008 (3)	0.0437 (7)
H6A	0.5534	0.7423	0.1055	0.052*
H6B	0.5896	0.6049	0.2387	0.052*
C7	0.63300 (16)	0.9214 (6)	0.2598 (3)	0.0373 (6)
C8	0.69713 (16)	0.8951 (6)	0.2350 (3)	0.0402 (7)
C9	0.75839 (19)	1.0441 (6)	0.2873 (3)	0.0487 (8)
H9	0.8011	1.0232	0.2710	0.058*
C10	0.7561 (2)	1.2220 (7)	0.3631 (3)	0.0577 (9)
H10	0.7969	1.3233	0.3973	0.069*
C11	0.6936 (2)	1.2508 (7)	0.3886 (3)	0.0602 (10)
H11	0.6923	1.3715	0.4404	0.072*
C12	0.6323 (2)	1.1010 (6)	0.3376 (3)	0.0497 (9)
H12	0.5903	1.1219	0.3560	0.060*

	U11	U22	U33	U12	U13	U23
Cl1	0.0570 (7)	0.0717 (9)	0.0516 (7)	0.000	0.0300 (6)	0.000
O1	0.0385 (12)	0.0598 (15)	0.0739 (16)	0.0029 (12)	0.0364 (12)	−0.0173 (13)
O2	0.129 (5)	0.104 (5)	0.049 (3)	−0.032 (5)	0.030 (3)	0.005 (4)
O3	0.070 (4)	0.208 (9)	0.164 (8)	−0.059 (5)	0.024 (5)	−0.032 (7)
O4	0.186 (10)	0.093 (5)	0.134 (8)	0.077 (6)	0.068 (7)	0.035 (5)
O5	0.149 (7)	0.155 (7)	0.158 (7)	−0.022 (6)	0.126 (6)	−0.036 (6)
N1	0.0338 (13)	0.0600 (18)	0.0561 (16)	0.0066 (13)	0.0261 (13)	−0.0047 (15)
N2	0.0327 (13)	0.0398 (14)	0.0403 (13)	0.0037 (11)	0.0216 (11)	0.0041 (11)
N3	0.0438 (15)	0.0585 (19)	0.071 (2)	0.0188 (14)	0.0405 (15)	0.0297 (16)
C1	0.0305 (14)	0.0414 (16)	0.0445 (16)	0.0024 (14)	0.0231 (12)	0.0018 (15)
C2	0.0391 (17)	0.058 (2)	0.056 (2)	0.0027 (16)	0.0337 (15)	0.0047 (16)
C3	0.0413 (17)	0.056 (2)	0.0513 (19)	0.0182 (17)	0.0210 (15)	0.0041 (17)
C4	0.0421 (16)	0.0475 (18)	0.0392 (16)	0.0081 (16)	0.0172 (14)	0.0095 (15)
C6	0.0374 (15)	0.0441 (18)	0.0576 (19)	0.0147 (15)	0.0283 (14)	0.0126 (16)
C7	0.0371 (14)	0.0404 (16)	0.0362 (14)	0.0121 (15)	0.0179 (12)	0.0082 (15)
C8	0.0353 (16)	0.0486 (19)	0.0389 (15)	0.0111 (15)	0.0184 (13)	0.0056 (15)
C9	0.0408 (18)	0.057 (2)	0.0479 (19)	0.0026 (15)	0.0195 (16)	0.0043 (16)
C10	0.053 (2)	0.061 (2)	0.047 (2)	−0.0041 (19)	0.0118 (17)	0.0012 (19)
C11	0.072 (2)	0.056 (2)	0.0398 (18)	0.014 (2)	0.0133 (17)	−0.0103 (16)
C12	0.053 (2)	0.058 (2)	0.0429 (18)	0.0198 (18)	0.0262 (16)	0.0046 (16)

Cl1—O5i	1.375 (6)	C1—C2	1.431 (4)
Cl1—O5	1.375 (6)	C2—H2A	0.9300
Cl1—O3	1.380 (5)	C3—C4	1.350 (5)
Cl1—O3i	1.380 (5)	C3—H3A	0.9300
Cl1—O4i	1.390 (5)	C4—H4	0.9300
Cl1—O4	1.390 (5)	C6—C7	1.503 (5)
Cl1—O2i	1.435 (4)	C6—H6A	0.9700
Cl1—O2	1.435 (4)	C6—H6B	0.9700
O1—C8	1.373 (4)	C7—C12	1.381 (4)
O1—H1	0.840 (11)	C7—C8	1.394 (4)
N1—C2	1.295 (4)	C8—C9	1.385 (4)
N1—C3	1.356 (4)	C9—C10	1.369 (5)
N2—C1	1.339 (4)	C9—H9	0.9300
N2—C4	1.353 (4)	C10—C11	1.368 (5)
N2—H2	0.883 (11)	C10—H10	0.9300
N3—C1	1.328 (4)	C11—C12	1.388 (5)
N3—C6	1.461 (4)	C11—H11	0.9300
N3—H3	0.877 (11)	C12—H12	0.9300
O5—Cl1—O3	111.1 (4)	N2—C4—H4	119.3
O5—Cl1—O4	111.9 (5)	N3—C6—C7	114.6 (3)
O3—Cl1—O4	111.9 (4)	N3—C6—H6A	108.6
O5—Cl1—O2	108.4 (4)	C7—C6—H6A	108.6
O3—Cl1—O2	106.8 (4)	N3—C6—H6B	108.6
O4—Cl1—O2	106.4 (4)	C7—C6—H6B	108.6
C8—O1—H1	107 (4)	H6A—C6—H6B	107.6
C2—N1—C3	117.4 (3)	C12—C7—C8	118.0 (3)
C1—N2—C4	118.6 (2)	C12—C7—C6	124.3 (3)
C1—N2—H2	130 (4)	C8—C7—C6	117.7 (3)
C4—N2—H2	111 (4)	O1—C8—C9	122.4 (3)
C1—N3—C6	125.6 (3)	O1—C8—C7	116.6 (3)
C1—N3—H3	115 (3)	C9—C8—C7	121.0 (3)
C6—N3—H3	120 (3)	C10—C9—C8	120.0 (3)
N3—C1—N2	121.9 (2)	C10—C9—H9	120.0
N3—C1—C2	120.1 (3)	C8—C9—H9	120.0
N2—C1—C2	117.9 (3)	C11—C10—C9	119.9 (4)
N1—C2—C1	123.0 (3)	C11—C10—H10	120.0
N1—C2—H2A	118.5	C9—C10—H10	120.0
C1—C2—H2A	118.5	C10—C11—C12	120.5 (3)
C4—C3—N1	121.6 (3)	C10—C11—H11	119.8
C4—C3—H3A	119.2	C12—C11—H11	119.8
N1—C3—H3A	119.2	C7—C12—C11	120.7 (3)
C3—C4—N2	121.4 (3)	C7—C12—H12	119.7
C3—C4—H4	119.3	C11—C12—H12	119.7
C6—N3—C1—N2	2.6 (5)	N3—C6—C7—C8	−175.6 (3)
C6—N3—C1—C2	−178.1 (3)	C12—C7—C8—O1	−179.2 (3)
C4—N2—C1—N3	−179.0 (3)	C6—C7—C8—O1	1.2 (4)
C4—N2—C1—C2	1.7 (4)	C12—C7—C8—C9	0.3 (4)
C3—N1—C2—C1	−1.5 (5)	C6—C7—C8—C9	−179.3 (3)
N3—C1—C2—N1	179.9 (3)	O1—C8—C9—C10	178.6 (3)
N2—C1—C2—N1	−0.7 (5)	C7—C8—C9—C10	−0.9 (5)
C2—N1—C3—C4	2.8 (5)	C8—C9—C10—C11	0.8 (5)
N1—C3—C4—N2	−1.8 (5)	C9—C10—C11—C12	−0.2 (5)
C1—N2—C4—C3	−0.5 (5)	C8—C7—C12—C11	0.3 (5)
C1—N3—C6—C7	74.2 (4)	C6—C7—C12—C11	179.9 (3)
N3—C6—C7—C12	4.9 (4)	C10—C11—C12—C7	−0.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ii	0.84 (1)	1.99 (2)	2.813 (3)	168 (5)
N2—H2···N2iii	0.88 (1)	1.93 (2)	2.793 (5)	166 (6)
N3—H3···O2	0.88 (1)	2.04 (2)	2.868 (7)	158 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.84 (1)	1.99 (2)	2.813 (3)	168 (5)
N2—H2⋯N2ii	0.88 (1)	1.93 (2)	2.793 (5)	166 (6)
N3—H3⋯O2	0.88 (1)	2.04 (2)	2.868 (7)	158 (4)

Symmetry codes: (i) ; (ii) .