9-(2-Pyridylmeth­oxy)-1,10-phenanthrolin-1-ium perchlorate methanol solvate

Zhang, S.G.; Hou, C.

doi:10.1107/S1600536808020606

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1450

doi:10.1107/S1600536808020606

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9-(2-Pyridylmethoxy)-1,10-phenanthrolin-1-ium perchlorate methanol solvate

Shi Guo Zhang ^a ^* and Chao Hou ^b

^aDepartment of Chemistry and Chemical Engineering, Institute of Materials Chemistry, Binzhou University, Binzhou 256603, People's Republic of China, and ^bDepartment of Chemistry, Shandong Normal University, Jinan 250014, People's Republic of China
^*Correspondence e-mail: zhangshiguo1970@yahoo.com.cn

(Received 13 June 2008; accepted 3 July 2008; online 9 July 2008)

In the title organic salt, C₁₈H₁₄N₃O⁺·ClO₄⁻·CH₄O, there is a π–π stacking interaction between neighbouring 1,10-phenanthroline rings and the relevant distances are 3.5453 (18) Å for the centroid–centroid distance and 3.354 Å for the perpendicular distance. There is also a relatively close contact between a C—H bond and a symmetry-related pyridine ring. There are classical N—H⋯O and O—H⋯N hydrogen bonds and non-classical C—H⋯O hydrogen bonds involving the cation, methanol solvent molecule and perchlorate anion.

Related literature

For a related structure, see: Liu et al. (2008 ).

Experimental

Crystal data

C₁₈H₁₄N₃O⁺·ClO₄⁻·CH₄O
M_r = 419.81
Triclinic, $[P \overline 1]$
a = 7.0765 (15) Å
b = 10.597 (2) Å
c = 14.164 (3) Å
α = 110.003 (3)°
β = 94.999 (3)°
γ = 105.304 (3)°
V = 944.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 298 (2) K
0.38 × 0.31 × 0.18 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.912, T_max = 0.957
5027 measured reflections
3504 independent reflections
2695 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.164
S = 1.05
3504 reflections
263 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H4⋯O6	0.81	1.85	2.648 (3)	167
O6—H5⋯N3	0.89	1.85	2.738 (4)	175
C3—H3⋯O2	0.93	2.32	3.238 (5)	170
C13—H13B⋯O6	0.97	2.58	3.405 (4)	143
C8—H8⋯Cg3ⁱ	0.93	2.81	3.650 (2)	151
Symmetry code: (i) -x+1, -y, -z+1. Cg3 is the centroid of the pyridine ring

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); 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 local programs.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808020606/bq2085sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808020606/bq2085Isup2.hkl

checkCIF report

Comment top

Derivatives of 1,10-phenanthroline play an important role in modern coordination chemistry (Liu et al., 2008) and we have tried to prepare a complex containing Manganese(II) and iron(III) metallic ions and 2-((pyridin-2-yl)methoxy)-1,10-phenanthroline ligand, but we obtained the title organic salt.

Fig. 1 shows the structure, revealing that one of N atoms from phenanthroline ring was protonated and it was turned into a cation. There is a π-π stacking interaction involving symmetry-related 1,10-phenanthroline rings, the relevant distances being Cg1···Cg2ⁱ = 3.5453 (18) Å and Cg1···Cg2ⁱ_perp = 3.354 Å and α = 1.09°; there also exits interaction between C8-H8 bond and pyridine ring and the relevant distance is H8···Cg3ⁱⁱ = 2.81 Å for H8 atom to the centroid of the pyridine ring and H8···Cg3ⁱⁱ_perp = 2.803 Å for the perpendicular distance from H8 atom to the pyridine ring plane [symmetry code: (i) -X, -Y, 1-Z; (ii) 1-X, -Y, 1-Z; Cg1, Cg2 and Cg3 are the centroids of the N2/C6C7C10-C12 ring, C4-C9 ring and N3/C14-C18 rings, respectively; Cg1···Cg2ⁱ_perp is the perpendicular distance from ring Cg1 to ring Cg2ⁱ; α is the dihedral angle between ring plane Cg1 and ring plane Cg2ⁱ; ]. There exist N-H···O and O-H···N classic hydrogen bonds and C-H···O non-classic hydrogen bonds (Fig. 1 and Table 1) in the asymmetric unit.

Related literature top

For a related structure, see: Liu et al. (2008).

Experimental top

10 ml methanol solution of 2-((pyridin-2-yl)methoxy)-1,10-phenanthroline (0.1200 g, 0.418 mmol) was added into 20 ml methanol solution containing FeCl₃.6H₂O (0.0565 g, 0.209 mmol) and Mn(ClO₄)₂.6H₂O (0.0757 g, 0.209 mmol), and the mixed solution was stirred for half a hour. Yellow single crystals were obtained after the solution had been allowed to stand at room temperature for three days.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and local programs.

Figures top

	Fig. 1. Structure of title organic salt with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. The classic hydrogen bonds are shown as dashed lines and non-classic hydrogen bonds as double dashed lines.
	Fig. 2. The packing and π-π stacking interaction (dashed lines) and C—H···π interaction (dashed lines), the methanol molecule and perchlorate anion have been omitted for clarity.

9-(2-Pyridylmethoxy)-1,10-phenanthrolin-1-ium perchlorate methanol solvate top

Crystal data top

C₁₈H₁₄N₃O⁺·ClO₄⁻·CH₄O	Z = 2
M_r = 419.81	F(000) = 436
Triclinic, P1	D_x = 1.477 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0765 (15) Å	Cell parameters from 1588 reflections
b = 10.597 (2) Å	θ = 3.0–25.9°
c = 14.164 (3) Å	µ = 0.25 mm⁻¹
α = 110.003 (3)°	T = 298 K
β = 94.999 (3)°	Block, yellow
γ = 105.304 (3)°	0.38 × 0.31 × 0.18 mm
V = 944.1 (3) Å³

Data collection top

Bruker SMART APEX CCD diffractometer	3504 independent reflections
Radiation source: fine-focus sealed tube	2695 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 25.7°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→8
T_min = 0.912, T_max = 0.957	k = −12→12
5027 measured reflections	l = −17→17

Refinement top

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0858P)² + 0.2952P] where P = (F_o² + 2F_c²)/3
3504 reflections	(Δ/σ)_max = 0.002
263 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₈H₁₄N₃O⁺·ClO₄⁻·CH₄O	γ = 105.304 (3)°
M_r = 419.81	V = 944.1 (3) Å³
Triclinic, P1	Z = 2
a = 7.0765 (15) Å	Mo Kα radiation
b = 10.597 (2) Å	µ = 0.25 mm⁻¹
c = 14.164 (3) Å	T = 298 K
α = 110.003 (3)°	0.38 × 0.31 × 0.18 mm
β = 94.999 (3)°

Data collection top

Bruker SMART APEX CCD diffractometer	3504 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2695 reflections with I > 2σ(I)
T_min = 0.912, T_max = 0.957	R_int = 0.020
5027 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.164	H-atom parameters constrained
S = 1.05	Δρ_max = 0.42 e Å⁻³
3504 reflections	Δρ_min = −0.23 e Å⁻³
263 parameters

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.

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.

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

	x	y	z	U_iso*/U_eq
C1	0.2377 (5)	0.4244 (3)	0.6774 (2)	0.0530 (7)
H1	0.2292	0.4775	0.7435	0.064*
C2	0.2448 (5)	0.4829 (3)	0.6041 (3)	0.0613 (8)
H2	0.2393	0.5744	0.6204	0.074*
C3	0.2598 (5)	0.4057 (3)	0.5080 (2)	0.0546 (7)
H3	0.2663	0.4450	0.4584	0.066*
C4	0.2655 (4)	0.2661 (3)	0.4831 (2)	0.0430 (6)
C5	0.2549 (4)	0.2104 (3)	0.55982 (18)	0.0374 (6)
C6	0.2521 (3)	0.0678 (3)	0.53855 (18)	0.0349 (5)
C7	0.2587 (4)	−0.0143 (3)	0.43867 (19)	0.0402 (6)
C8	0.2705 (4)	0.0441 (3)	0.3616 (2)	0.0471 (7)
H8	0.2750	−0.0120	0.2955	0.057*
C9	0.2753 (4)	0.1789 (3)	0.3827 (2)	0.0485 (7)
H9	0.2851	0.2153	0.3315	0.058*
C10	0.2529 (4)	−0.1564 (3)	0.4190 (2)	0.0443 (6)
H10	0.2592	−0.2151	0.3541	0.053*
C11	0.2382 (4)	−0.2049 (3)	0.4948 (2)	0.0455 (6)
H11	0.2333	−0.2976	0.4831	0.055*
C12	0.2304 (4)	−0.1128 (3)	0.59278 (19)	0.0386 (6)
C13	0.2012 (4)	−0.0886 (3)	0.7665 (2)	0.0490 (7)
H13A	0.1173	−0.1480	0.7956	0.059*
H13B	0.1426	−0.0160	0.7652	0.059*
C14	0.4068 (4)	−0.0208 (3)	0.8319 (2)	0.0460 (7)
C15	0.5178 (5)	−0.1004 (3)	0.8526 (2)	0.0557 (8)
H15	0.4653	−0.1986	0.8265	0.067*
C16	0.7067 (5)	−0.0345 (4)	0.9121 (3)	0.0692 (9)
H16	0.7833	−0.0868	0.9270	0.083*
C17	0.7788 (6)	0.1094 (4)	0.9488 (3)	0.0753 (10)
H17	0.9061	0.1570	0.9890	0.090*
C18	0.6621 (6)	0.1827 (4)	0.9257 (3)	0.0720 (10)
H18	0.7132	0.2808	0.9511	0.086*
C19	0.2308 (7)	0.3748 (4)	0.9157 (3)	0.0887 (12)
H19A	0.2483	0.3543	0.9762	0.133*
H19B	0.1107	0.4000	0.9102	0.133*
H19C	0.3431	0.4521	0.9197	0.133*
Cl1	0.20777 (12)	0.45705 (7)	0.21213 (5)	0.0541 (3)
N1	0.2429 (3)	0.2941 (2)	0.65502 (16)	0.0419 (5)
H4	0.2362	0.2694	0.7032	0.050*
N2	0.2387 (3)	0.0189 (2)	0.61631 (15)	0.0377 (5)
N3	0.4780 (4)	0.1207 (3)	0.86832 (19)	0.0580 (7)
O1	0.2091 (3)	−0.17350 (18)	0.66282 (14)	0.0476 (5)
O2	0.2322 (8)	0.5077 (4)	0.3177 (2)	0.1432 (16)
O3	0.2709 (7)	0.5724 (3)	0.1857 (3)	0.1279 (13)
O4	0.3128 (7)	0.3648 (4)	0.1769 (3)	0.1583 (17)
O5	0.0081 (6)	0.3882 (4)	0.1659 (3)	0.1494 (16)
O6	0.2165 (4)	0.2545 (2)	0.82875 (15)	0.0664 (6)
H5	0.3072	0.2151	0.8417	0.100*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0681 (19)	0.0396 (14)	0.0503 (16)	0.0211 (14)	0.0085 (14)	0.0135 (12)
C2	0.080 (2)	0.0411 (15)	0.068 (2)	0.0208 (15)	0.0100 (17)	0.0261 (15)
C3	0.0631 (19)	0.0527 (17)	0.0588 (18)	0.0173 (15)	0.0088 (15)	0.0356 (15)
C4	0.0392 (14)	0.0474 (15)	0.0473 (15)	0.0123 (12)	0.0085 (12)	0.0248 (12)
C5	0.0343 (13)	0.0415 (13)	0.0373 (13)	0.0109 (11)	0.0062 (10)	0.0170 (11)
C6	0.0291 (12)	0.0387 (13)	0.0363 (13)	0.0085 (10)	0.0057 (10)	0.0156 (10)
C7	0.0315 (13)	0.0474 (14)	0.0397 (14)	0.0116 (11)	0.0057 (10)	0.0149 (11)
C8	0.0455 (15)	0.0615 (17)	0.0344 (13)	0.0174 (13)	0.0117 (11)	0.0169 (12)
C9	0.0496 (16)	0.0619 (18)	0.0435 (15)	0.0187 (14)	0.0125 (12)	0.0298 (13)
C10	0.0430 (15)	0.0437 (14)	0.0389 (14)	0.0149 (12)	0.0062 (11)	0.0064 (11)
C11	0.0461 (15)	0.0361 (13)	0.0488 (16)	0.0137 (12)	0.0051 (12)	0.0100 (12)
C12	0.0339 (13)	0.0379 (13)	0.0434 (14)	0.0105 (11)	0.0031 (11)	0.0162 (11)
C13	0.0567 (17)	0.0508 (16)	0.0479 (16)	0.0167 (14)	0.0156 (13)	0.0276 (13)
C14	0.0619 (18)	0.0460 (15)	0.0369 (14)	0.0193 (13)	0.0143 (12)	0.0211 (12)
C15	0.075 (2)	0.0495 (16)	0.0492 (17)	0.0266 (15)	0.0100 (15)	0.0215 (13)
C16	0.078 (2)	0.080 (2)	0.060 (2)	0.039 (2)	0.0054 (17)	0.0305 (18)
C17	0.072 (2)	0.082 (3)	0.061 (2)	0.019 (2)	−0.0055 (17)	0.0218 (19)
C18	0.085 (3)	0.0527 (18)	0.065 (2)	0.0110 (18)	−0.0040 (18)	0.0188 (16)
C19	0.124 (4)	0.088 (3)	0.057 (2)	0.051 (3)	0.022 (2)	0.0168 (19)
Cl1	0.0777 (6)	0.0433 (4)	0.0435 (4)	0.0249 (4)	0.0107 (3)	0.0149 (3)
N1	0.0504 (13)	0.0393 (11)	0.0388 (12)	0.0157 (10)	0.0074 (10)	0.0173 (9)
N2	0.0398 (12)	0.0377 (11)	0.0367 (11)	0.0126 (9)	0.0070 (9)	0.0152 (9)
N3	0.0745 (18)	0.0465 (14)	0.0524 (15)	0.0183 (13)	0.0056 (13)	0.0201 (11)
O1	0.0615 (12)	0.0371 (9)	0.0455 (11)	0.0141 (9)	0.0073 (9)	0.0189 (8)
O2	0.287 (5)	0.119 (3)	0.0502 (16)	0.101 (3)	0.037 (2)	0.0340 (17)
O3	0.204 (4)	0.087 (2)	0.108 (2)	0.035 (2)	0.043 (2)	0.0598 (19)
O4	0.217 (4)	0.144 (3)	0.135 (3)	0.143 (3)	0.026 (3)	0.015 (2)
O5	0.096 (3)	0.119 (3)	0.166 (4)	−0.003 (2)	−0.004 (2)	0.010 (3)
O6	0.0970 (17)	0.0684 (14)	0.0451 (12)	0.0420 (13)	0.0156 (11)	0.0226 (10)

Geometric parameters (Å, º) top

C1—N1	1.318 (3)	C13—O1	1.451 (3)
C1—C2	1.377 (4)	C13—C14	1.500 (4)
C1—H1	0.9300	C13—H13A	0.9700
C2—C3	1.357 (4)	C13—H13B	0.9700
C2—H2	0.9300	C14—N3	1.340 (4)
C3—C4	1.411 (4)	C14—C15	1.377 (4)
C3—H3	0.9300	C15—C16	1.375 (5)
C4—C5	1.402 (4)	C15—H15	0.9300
C4—C9	1.426 (4)	C16—C17	1.362 (5)
C5—N1	1.361 (3)	C16—H16	0.9300
C5—C6	1.431 (3)	C17—C18	1.363 (5)
C6—N2	1.368 (3)	C17—H17	0.9300
C6—C7	1.397 (3)	C18—N3	1.337 (4)
C7—C10	1.423 (4)	C18—H18	0.9300
C7—C8	1.425 (4)	C19—O6	1.410 (4)
C8—C9	1.346 (4)	C19—H19A	0.9600
C8—H8	0.9300	C19—H19B	0.9600
C9—H9	0.9300	C19—H19C	0.9600
C10—C11	1.340 (4)	Cl1—O4	1.368 (3)
C10—H10	0.9300	Cl1—O3	1.375 (3)
C11—C12	1.413 (4)	Cl1—O2	1.383 (3)
C11—H11	0.9300	Cl1—O5	1.388 (4)
C12—N2	1.303 (3)	N1—H4	0.8111
C12—O1	1.354 (3)	O6—H5	0.8900

N1—C1—C2	120.9 (3)	C14—C13—H13A	109.5
N1—C1—H1	119.6	O1—C13—H13B	109.5
C2—C1—H1	119.6	C14—C13—H13B	109.5
C3—C2—C1	119.4 (3)	H13A—C13—H13B	108.1
C3—C2—H2	120.3	N3—C14—C15	121.6 (3)
C1—C2—H2	120.3	N3—C14—C13	116.9 (3)
C2—C3—C4	120.3 (3)	C15—C14—C13	121.5 (3)
C2—C3—H3	119.9	C16—C15—C14	119.8 (3)
C4—C3—H3	119.9	C16—C15—H15	120.1
C5—C4—C3	118.2 (2)	C14—C15—H15	120.1
C5—C4—C9	119.1 (2)	C17—C16—C15	118.4 (3)
C3—C4—C9	122.7 (2)	C17—C16—H16	120.8
N1—C5—C4	118.6 (2)	C15—C16—H16	120.8
N1—C5—C6	120.4 (2)	C16—C17—C18	119.2 (3)
C4—C5—C6	121.0 (2)	C16—C17—H17	120.4
N2—C6—C7	123.9 (2)	C18—C17—H17	120.4
N2—C6—C5	118.3 (2)	N3—C18—C17	123.4 (3)
C7—C6—C5	117.8 (2)	N3—C18—H18	118.3
C6—C7—C10	116.8 (2)	C17—C18—H18	118.3
C6—C7—C8	120.5 (2)	O6—C19—H19A	109.5
C10—C7—C8	122.7 (2)	O6—C19—H19B	109.5
C9—C8—C7	121.2 (2)	H19A—C19—H19B	109.5
C9—C8—H8	119.4	O6—C19—H19C	109.5
C7—C8—H8	119.4	H19A—C19—H19C	109.5
C8—C9—C4	120.4 (2)	H19B—C19—H19C	109.5
C8—C9—H9	119.8	O4—Cl1—O3	111.0 (3)
C4—C9—H9	119.8	O4—Cl1—O2	111.7 (2)
C11—C10—C7	119.4 (2)	O3—Cl1—O2	107.0 (2)
C11—C10—H10	120.3	O4—Cl1—O5	108.2 (3)
C7—C10—H10	120.3	O3—Cl1—O5	107.6 (3)
C10—C11—C12	119.0 (2)	O2—Cl1—O5	111.2 (3)
C10—C11—H11	120.5	C1—N1—C5	122.6 (2)
C12—C11—H11	120.5	C1—N1—H4	113.1
N2—C12—O1	121.1 (2)	C5—N1—H4	124.3
N2—C12—C11	124.7 (2)	C12—N2—C6	116.2 (2)
O1—C12—C11	114.2 (2)	C18—N3—C14	117.6 (3)
O1—C13—C14	110.5 (2)	C12—O1—C13	119.09 (19)
O1—C13—H13A	109.5	C19—O6—H5	109.6

N1—C1—C2—C3	−0.8 (5)	C7—C10—C11—C12	−0.5 (4)
C1—C2—C3—C4	0.8 (5)	C10—C11—C12—N2	−0.8 (4)
C2—C3—C4—C5	0.1 (4)	C10—C11—C12—O1	177.9 (2)
C2—C3—C4—C9	178.2 (3)	O1—C13—C14—N3	115.5 (3)
C3—C4—C5—N1	−1.1 (4)	O1—C13—C14—C15	−63.9 (3)
C9—C4—C5—N1	−179.2 (2)	N3—C14—C15—C16	0.0 (4)
C3—C4—C5—C6	177.5 (2)	C13—C14—C15—C16	179.3 (3)
C9—C4—C5—C6	−0.6 (4)	C14—C15—C16—C17	−0.2 (5)
N1—C5—C6—N2	−0.5 (3)	C15—C16—C17—C18	0.2 (5)
C4—C5—C6—N2	−179.1 (2)	C16—C17—C18—N3	0.0 (6)
N1—C5—C6—C7	178.1 (2)	C2—C1—N1—C5	−0.1 (4)
C4—C5—C6—C7	−0.5 (4)	C4—C5—N1—C1	1.1 (4)
N2—C6—C7—C10	−0.6 (4)	C6—C5—N1—C1	−177.5 (2)
C5—C6—C7—C10	−179.1 (2)	O1—C12—N2—C6	−177.3 (2)
N2—C6—C7—C8	179.3 (2)	C11—C12—N2—C6	1.3 (4)
C5—C6—C7—C8	0.8 (4)	C7—C6—N2—C12	−0.6 (3)
C6—C7—C8—C9	−0.1 (4)	C5—C6—N2—C12	178.0 (2)
C10—C7—C8—C9	179.9 (3)	C17—C18—N3—C14	−0.2 (5)
C7—C8—C9—C4	−1.0 (4)	C15—C14—N3—C18	0.2 (4)
C5—C4—C9—C8	1.3 (4)	C13—C14—N3—C18	−179.2 (3)
C3—C4—C9—C8	−176.7 (3)	N2—C12—O1—C13	−1.8 (3)
C6—C7—C10—C11	1.1 (4)	C11—C12—O1—C13	179.4 (2)
C8—C7—C10—C11	−178.8 (2)	C14—C13—O1—C12	−90.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H4···O6	0.81	1.85	2.648 (3)	167
O6—H5···N3	0.89	1.85	2.738 (4)	175
C3—H3···O2	0.93	2.32	3.238 (5)	170
C13—H13B···O6	0.97	2.58	3.405 (4)	143
C8—H8···Cg3ⁱ	0.93	2.81	3.650 (2)	151

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₄N₃O⁺·ClO₄⁻·CH₄O
M_r	419.81
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.0765 (15), 10.597 (2), 14.164 (3)
α, β, γ (°)	110.003 (3), 94.999 (3), 105.304 (3)
V (Å³)	944.1 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.38 × 0.31 × 0.18

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.912, 0.957
No. of measured, independent and observed [I > 2σ(I)] reflections	5027, 3504, 2695
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.164, 1.05
No. of reflections	3504
No. of parameters	263
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.23

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Sheldrick, 2008) and local programs.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H4···O6	0.81	1.85	2.648 (3)	167
O6—H5···N3	0.89	1.85	2.738 (4)	175
C3—H3···O2	0.93	2.32	3.238 (5)	170
C13—H13B···O6	0.97	2.58	3.405 (4)	143
C8—H8···Cg3ⁱ	0.93	2.81	3.650 (2)	151

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

The authors thank the Natural Science Foundation of Shandong Province of China (grant No. Y2007B26).

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Liu, Q. S., Liu, L. D. & Shi, J. M. (2008). Acta Cryst. C64, m58–m60. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar