2-[(2-Hy­droxy­benz­yl)amino]­pyrazinium perchlorate–2-[(pyrazin-2-yl­amino)­meth­yl]phenol (1/1)

Gao, S.; Ng, S.W.

doi:10.1107/S1600536812031558

organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2475

https://doi.org/10.1107/S1600536812031558

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2-[(2-Hydroxybenzyl)amino]pyrazinium perchlorate–2-[(pyrazin-2-ylamino)methyl]phenol (1/1)

Shan Gao ^a and Seik Weng Ng ^b,^c ^*

^aKey Laboratory of Functional Inorganic Material Chemistry, Ministry of Education, Heilongjiang University, Harbin 150080, People's Republic of China, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 25 June 2012; accepted 11 July 2012; online 18 July 2012)

In the crystal structure of the title co-crystal, C₁₁H₁₂N₃O⁺·ClO₄⁻·C₁₁H₁₁N₃O, the perchlorate ion is disordered about a twofold rotation axis with the Cl atom located on the twofold rotation axis; the 2-[(2-hydroxybenzyl)amino]pyrazinium cation and the neutral 2-[(pyrazin-2-ylamino)methyl]phenol molecule are disordered about the rotation axis in a 1:1 ratio. These two are connected by a pyrazine–pyrazine N¹—H⋯N⁴ hydrogen bond. The cation, whose two aromatic rings are twisted along the –CH₂—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_r = 502.91
Monoclinic, C 2
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.116
S = 1.02
2272 reflections
188 parameters
49 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.29 e Å⁻³
Absolute structure: Flack (1983 ), 970 Friedel pairs
Flack parameter: 0.08 (12)

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) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) -x+1, y, -z.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812031558/xu5583sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812031558/xu5583Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812031558/xu5583Isup3.cml

checkCIF report

Comment top

Salicylaldehyde condenses with romatic amines to yield Schiff bases, which serve as chelating ligands to a plethora of metal systems. These Schiff bases can be readily reduce to the corresponding secondary amines, which can also function as chelating ligands. Curiously, there are only few 2-(arylamino)methylphenols compared with the plethora of Schiff bases in the chemical literature. We have communicated the crystal structure of 2-{[(pyrazin-2-yl)amino]methyl}phenol (Gao & Ng, 2012). The compound reacts with half a molar equivalent of perchloric acid to form the co-crystal, C₁₁H₁₂N₃O⁺.ClO₄^-.C₁₁H₁₁N₃ (Scheme I). The C₁₁H₁₂N₃O⁺ cation and the neutral C₁₁H₁₁N₃O molecule are disordered about the same position in a 1:1 ratio. The crystal structure is interpreted in terms of the cation and neutral molecule being an N_1-pyrazine–H···N_4-pyrazine hydrogen bond. The cation, whose two aromatic rings are twisted along the –CH₂–NH– bond by 76.8 (1) °, is hydrogen-bond donor to the perchlorate ion through the N atom of this link.

Related literature top

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

Experimental top

A solution of 2-aminopyrazine (1 mmol) and salicylaldehyde (1 mmol) in toluene (50 ml) was heated for 10 h. The solvent was removed under vacuum, and the residue was reduced in absolute methanol by sodium borohydride. Light yellow crystals were obtained by recrystallization from methanol to which several drops of perchloric acid were added.

Structure description top

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

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); 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).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₁₁H₁₂N₃O⁺.ClO₄^-.C₁₁H₁₁N₃O at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown.

2-[(2-Hydroxybenzyl)amino]pyrazinium perchlorate–2-[(pyrazin-2-ylamino)methyl]phenol (1/1) top

Crystal data top

C₁₁H₁₂N₃O⁺·ClO₄⁻·C₁₁H₁₁N₃O	F(000) = 524
M_r = 502.91	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0572P)² + 0.4309P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2272 reflections	Δρ_max = 0.25 e Å⁻³
188 parameters	Δρ_min = −0.29 e Å⁻³
49 restraints	Absolute structure: Flack (1983), 970 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.08 (12)

Crystal data top

C₁₁H₁₂N₃O⁺·ClO₄⁻·C₁₁H₁₁N₃O	V = 1152.68 (16) Å³
M_r = 502.91	Z = 2
Monoclinic, C2	Mo Kα radiation
a = 19.3402 (14) Å	µ = 0.22 mm⁻¹
b = 5.9467 (3) Å	T = 295 K
c = 11.1761 (9) Å	0.24 × 0.21 × 0.18 mm
β = 116.263 (10)°

Data collection top

Agilent Technologies Excalibur Eos diffractometer	2272 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	1859 reflections with I > 2σ(I)
T_min = 0.950, T_max = 0.962	R_int = 0.017
4085 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.116	Δρ_max = 0.25 e Å⁻³
S = 1.02	Δρ_min = −0.29 e Å⁻³
2272 reflections	Absolute structure: Flack (1983), 970 Friedel pairs
188 parameters	Absolute structure parameter: 0.08 (12)
49 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, y, −z+1.

Hydrogen-bond geometry (Å, º) top

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)

Symmetry codes: (ii) x+1/2, y−1/2, z; (iii) −x+1, y, −z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₂N₃O⁺·ClO₄⁻·C₁₁H₁₁N₃O
M_r	502.91
Crystal system, space group	Monoclinic, C2
Temperature (K)	295
a, b, c (Å)	19.3402 (14), 5.9467 (3), 11.1761 (9)
β (°)	116.263 (10)
V (Å³)	1152.68 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.24 × 0.21 × 0.18

Data collection
Diffractometer	Agilent Technologies Excalibur Eos
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.950, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	4085, 2272, 1859
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.116, 1.02
No. of reflections	2272
No. of parameters	188
No. of restraints	49
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.29
Absolute structure	Flack (1983), 970 Friedel pairs
Absolute structure parameter	0.08 (12)

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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) x+1/2, y−1/2, z; (ii) −x+1, y, −z.

Acknowledgements

We thank the Key Project of the Natural Science Foundation of Heilongjiang Province (grant No. ZD200903), the Key Project of the Education Bureau of Heilongjiang Province (grants No. 12511z023 and No. 2011CJHB006), the Innovation Team of the Education Bureau of Heilongjiang Province (grant No. 2010td03), Heilongjiang University (grant No. Hdtd2010–04) and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.

References

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Volume 68| Part 8| August 2012| Page o2475

https://doi.org/10.1107/S1600536812031558

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-[(2-Hy­dr­oxy­benz­yl)amino]­pyrazinium perchlorate–2-[(pyrazin-2-yl­amino)­meth­yl]phenol (1/1)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-[(2-Hydroxybenzyl)amino]pyrazinium perchlorate–2-[(pyrazin-2-ylamino)methyl]phenol (1/1)