2-(2-Pyridyl­amino)­pyridinium perchlorate displaying a one-dimensional hydrogen-bonding supramolecular chain

In the crystal structure of the title compound, C₁₀H₁₀N₃⁺·ClO₄^-, the cation adopts the normal trans-trans configuration and an approximately planar geometry. Hydro­gen-bonding interactions between the cations and perchlorate anions extend this structure into a one-dimensional chain architecture.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.069
• wR factor = 0.199
• Data-to-parameter ratio = 10.2

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT242_ALERT_2_A Check Low    U(eq) as Compared to Neighbors ....        Cl1

Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact  O3     ..  O3      ..       2.64 Ang.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       3.12 Ratio
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         N2
PLAT301_ALERT_3_C Main Residue  Disorder .........................      18.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT432_ALERT_2_C Short Inter X...Y Contact  C3     ..  O3'     ..       2.96 Ang.

   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

C10H10N3^+·ClO4^−	F(000) = 560
Mr = 271.66	Dx = 1.522 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P_2ybc	Cell parameters from 925 reflections
a = 8.527 (3) Å	θ = 2.7–21.4°
b = 16.174 (5) Å	µ = 0.33 mm^−1
c = 8.753 (3) Å	T = 293 K
β = 100.878 (6)°	Lamellar, colorless
V = 1185.5 (7) Å^3	0.24 × 0.20 × 0.08 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2033 independent reflections
Radiation source: fine-focus sealed tube	1165 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −10→7
Tmin = 0.866, Tmax = 0.970	k = −14→19
4794 measured reflections	l = −10→10

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.200	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.1137P)^2] where P = (Fo^2 + 2Fc^2)/3
2033 reflections	(Δ/σ)max = 0.001
200 parameters	Δρmax = 0.39 e Å^−3
110 restraints	Δρmin = −0.31 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.5632 (5)	0.4081 (2)	0.3345 (5)	0.0524 (11)
H1A	0.4741	0.4103	0.3668	0.063*
N2	0.5632 (5)	0.2676 (3)	0.3746 (5)	0.0619 (13)
H2A	0.6122	0.2219	0.3658	0.074*
N3	0.3454 (5)	0.3272 (3)	0.4496 (5)	0.0557 (12)
C1	0.6275 (7)	0.4786 (3)	0.2920 (6)	0.0597 (15)
H1	0.5759	0.5288	0.2987	0.072*
C2	0.7664 (7)	0.4766 (4)	0.2398 (6)	0.0657 (16)
H2	0.8109	0.5251	0.2098	0.079*
C3	0.8425 (7)	0.4010 (4)	0.2315 (7)	0.0660 (16)
H3	0.9389	0.3989	0.1964	0.079*
C4	0.7768 (7)	0.3307 (3)	0.2742 (6)	0.0590 (15)
H4	0.8271	0.2801	0.2675	0.071*
C5	0.6345 (6)	0.3342 (3)	0.3278 (6)	0.0448 (12)
C6	0.4247 (6)	0.2588 (3)	0.4348 (5)	0.0454 (12)
C7	0.3729 (6)	0.1816 (3)	0.4733 (6)	0.0535 (13)
H7	0.4309	0.1343	0.4601	0.064*
C8	0.2356 (7)	0.1765 (4)	0.5306 (7)	0.0672 (16)
H8	0.1985	0.1255	0.5577	0.081*
C9	0.1528 (7)	0.2472 (4)	0.5480 (7)	0.0693 (16)
H9	0.0590	0.2450	0.5876	0.083*
C10	0.2103 (7)	0.3213 (3)	0.5062 (7)	0.0615 (15)
H10	0.1534	0.3693	0.5176	0.074*
Cl1	0.79976 (15)	0.07711 (8)	0.25313 (15)	0.0535 (5)
O1	0.8893 (15)	0.1341 (6)	0.1885 (15)	0.118 (4)	0.564 (14)
O2	0.7529 (13)	0.0069 (6)	0.1559 (12)	0.089 (3)	0.564 (14)
O3	0.9093 (11)	0.0423 (7)	0.3879 (9)	0.124 (5)	0.564 (14)
O4	0.6739 (10)	0.1110 (6)	0.3156 (16)	0.102 (4)	0.564 (14)
O1'	0.9058 (18)	0.1027 (11)	0.1479 (18)	0.133 (7)	0.436 (14)
O2'	0.7787 (19)	−0.0073 (5)	0.244 (2)	0.116 (6)	0.436 (14)
O3'	0.877 (2)	0.1081 (14)	0.4022 (15)	0.234 (11)	0.436 (14)
O4'	0.6563 (10)	0.1244 (6)	0.1991 (16)	0.075 (4)	0.436 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.048 (2)	0.052 (3)	0.060 (3)	−0.001 (2)	0.018 (2)	0.001 (2)
N2	0.059 (3)	0.046 (3)	0.084 (3)	0.008 (2)	0.024 (3)	−0.002 (2)
N3	0.052 (3)	0.049 (3)	0.069 (3)	0.002 (2)	0.017 (2)	0.002 (2)
C1	0.064 (4)	0.043 (3)	0.074 (4)	0.000 (3)	0.018 (3)	0.005 (3)
C2	0.064 (4)	0.056 (4)	0.080 (4)	−0.009 (3)	0.023 (3)	0.011 (3)
C3	0.059 (3)	0.069 (4)	0.078 (4)	−0.001 (3)	0.033 (3)	−0.001 (3)
C4	0.063 (4)	0.046 (3)	0.074 (4)	0.008 (3)	0.027 (3)	0.003 (3)
C5	0.047 (3)	0.038 (3)	0.050 (3)	−0.002 (2)	0.011 (2)	0.003 (2)
C6	0.042 (3)	0.047 (3)	0.047 (3)	−0.005 (2)	0.009 (2)	−0.004 (2)
C7	0.054 (3)	0.045 (3)	0.063 (3)	−0.001 (3)	0.015 (3)	−0.004 (2)
C8	0.074 (4)	0.054 (4)	0.075 (4)	−0.019 (3)	0.020 (3)	0.004 (3)
C9	0.052 (3)	0.082 (5)	0.078 (4)	−0.008 (3)	0.022 (3)	−0.001 (3)
C10	0.056 (3)	0.056 (4)	0.075 (4)	−0.001 (3)	0.019 (3)	−0.008 (3)
Cl1	0.0494 (8)	0.0499 (8)	0.0611 (8)	−0.0010 (7)	0.0102 (6)	−0.0037 (7)
O1	0.140 (8)	0.080 (6)	0.155 (9)	−0.028 (6)	0.084 (7)	−0.009 (6)
O2	0.110 (7)	0.067 (6)	0.089 (6)	0.002 (5)	0.020 (5)	−0.023 (5)
O3	0.116 (7)	0.162 (9)	0.092 (6)	0.045 (6)	0.017 (6)	0.006 (6)
O4	0.081 (5)	0.090 (6)	0.144 (9)	0.023 (5)	0.046 (6)	−0.023 (6)
O1'	0.133 (10)	0.135 (11)	0.145 (10)	−0.005 (8)	0.066 (8)	0.019 (8)
O2'	0.124 (9)	0.070 (7)	0.152 (11)	−0.006 (6)	0.018 (9)	0.014 (7)
O3'	0.244 (14)	0.219 (14)	0.223 (14)	0.003 (10)	0.005 (10)	−0.005 (10)
O4'	0.072 (6)	0.058 (6)	0.093 (8)	0.016 (4)	0.009 (5)	−0.007 (5)

Geometric parameters (Å, º)

N1—C5	1.347 (6)	C6—C7	1.387 (7)
N1—C1	1.349 (6)	C7—C8	1.361 (7)
N1—H1A	0.8600	C7—H7	0.9300
N2—C5	1.338 (6)	C8—C9	1.367 (8)
N2—C6	1.388 (6)	C8—H8	0.9300
N2—H2A	0.8600	C9—C10	1.371 (7)
N3—C6	1.316 (6)	C9—H9	0.9300
N3—C10	1.341 (6)	C10—H10	0.9300
C1—C2	1.348 (8)	Cl1—O2'	1.377 (9)
C1—H1	0.9300	Cl1—O1	1.384 (7)
C2—C3	1.393 (8)	Cl1—O4	1.405 (6)
C2—H2	0.9300	Cl1—O2	1.430 (7)
C3—C4	1.352 (7)	Cl1—O3'	1.436 (10)
C3—H3	0.9300	Cl1—O4'	1.444 (8)
C4—C5	1.383 (6)	Cl1—O1'	1.467 (9)
C4—H4	0.9300	Cl1—O3	1.471 (7)
C5—N1—C1	121.9 (4)	C8—C9—C10	118.9 (5)
C5—N1—H1A	119.1	C8—C9—H9	120.5
C1—N1—H1A	119.1	C10—C9—H9	120.5
C5—N2—C6	131.8 (4)	N3—C10—C9	122.4 (5)
C5—N2—H2A	114.1	N3—C10—H10	118.8
C6—N2—H2A	114.1	C9—C10—H10	118.8
C6—N3—C10	118.1 (4)	O2'—Cl1—O1	135.4 (8)
C2—C1—N1	120.1 (5)	O2'—Cl1—O4	108.0 (8)
C2—C1—H1	119.9	O1—Cl1—O4	114.8 (6)
N1—C1—H1	119.9	O1—Cl1—O2	113.5 (6)
C1—C2—C3	119.2 (5)	O4—Cl1—O2	113.2 (5)
C1—C2—H2	120.4	O2'—Cl1—O3'	115.5 (8)
C3—C2—H2	120.4	O1—Cl1—O3'	86.9 (10)
C4—C3—C2	120.2 (5)	O4—Cl1—O3'	76.2 (9)
C4—C3—H3	119.9	O2—Cl1—O3'	147.9 (9)
C2—C3—H3	119.9	O2'—Cl1—O4'	114.4 (7)
C3—C4—C5	119.7 (5)	O1—Cl1—O4'	90.7 (7)
C3—C4—H4	120.2	O2—Cl1—O4'	95.8 (6)
C5—C4—H4	120.2	O3'—Cl1—O4'	109.1 (8)
N2—C5—N1	117.7 (4)	O2'—Cl1—O1'	109.4 (8)
N2—C5—C4	123.3 (4)	O4—Cl1—O1'	137.8 (8)
N1—C5—C4	118.9 (4)	O2—Cl1—O1'	89.2 (8)
N3—C6—C7	122.7 (5)	O3'—Cl1—O1'	104.0 (9)
N3—C6—N2	116.2 (4)	O4'—Cl1—O1'	103.3 (7)
C7—C6—N2	121.1 (5)	O2'—Cl1—O3	73.9 (7)
C8—C7—C6	118.7 (5)	O1—Cl1—O3	105.5 (7)
C8—C7—H7	120.7	O4—Cl1—O3	104.7 (6)
C6—C7—H7	120.7	O2—Cl1—O3	103.7 (5)
C7—C8—C9	119.2 (5)	O3'—Cl1—O3	45.0 (8)
C7—C8—H8	120.4	O4'—Cl1—O3	146.6 (6)
C9—C8—H8	120.4	O1'—Cl1—O3	103.8 (8)
C5—N1—C1—C2	0.5 (8)	C10—N3—C6—C7	0.9 (7)
N1—C1—C2—C3	−0.4 (8)	C10—N3—C6—N2	179.5 (4)
C1—C2—C3—C4	0.5 (9)	C5—N2—C6—N3	0.3 (8)
C2—C3—C4—C5	−0.7 (8)	C5—N2—C6—C7	179.0 (5)
C6—N2—C5—N1	−1.5 (8)	N3—C6—C7—C8	−0.9 (8)
C6—N2—C5—C4	178.2 (5)	N2—C6—C7—C8	−179.5 (5)
C1—N1—C5—N2	179.0 (4)	C6—C7—C8—C9	0.2 (8)
C1—N1—C5—C4	−0.7 (7)	C7—C8—C9—C10	0.4 (9)
C3—C4—C5—N2	−178.9 (5)	C6—N3—C10—C9	−0.2 (8)
C3—C4—C5—N1	0.8 (7)	C8—C9—C10—N3	−0.4 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N3	0.86	1.96	2.623 (6)	133
N1—H1A···O2^i	0.86	2.47	3.149 (5)	137
N2—H2A···O4	0.86	1.94	2.785 (6)	166

Symmetry code: (i) −x+1, y+1/2, −z+1/2.