Quinolinium perchlorate

The crystal structure of the title compound, C₉H₈N⁺·ClO₄⁻, consists of cations and anions linked by N—H...O and C—H...O hydrogen bonds to form layers parallel to the (102) plane.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.038
• wR factor = 0.108
• Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         Cl

Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5     ..  O3      ..       2.62 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   1 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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXTL (Sheldrick, 2003); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and Mercury (Version 1.3; Bruno et al., 2002); software used to prepare material for publication: PLATON (Spek, 2003).

Quinolinum perchlorate

Crystal data

C9H8N^+·ClO4^−	F(000) = 472
Mr = 229.61	Dx = 1.576 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7554 reflections
a = 5.4935 (5) Å	θ = 1.8–30.3°
b = 22.3315 (10) Å	µ = 0.39 mm^−1
c = 7.9970 (4) Å	T = 291 K
β = 99.401 (6)°	Prism, colourless
V = 967.88 (11) Å^3	0.6 × 0.3 × 0.2 mm
Z = 4

Data collection

Kuma KM-4 CCD diffractometer	1921 reflections with I > 2σ(I)
Radiation source: CX-Mo12x0.4-S Seifert Mo tube	Rint = 0.023
Graphite monochromator	θmax = 27.5°, θmin = 3.2°
Detector resolution: 8.2356 pixels mm^-1	h = −5→7
ω scans	k = −28→28
8865 measured reflections	l = −10→10
2190 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	All H-atom parameters refined
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.0527P)^2 + 0.3838P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
2190 reflections	Δρmax = 0.26 e Å^−3
169 parameters	Δρmin = −0.36 e Å^−3
0 restraints	Extinction correction: SHELXL97, FC^*=KFC[1+0.001XFC^2Λ^3/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.030 (3)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
N1	0.7265 (3)	0.85760 (7)	0.1929 (2)	0.0492 (5)
C2	0.7206 (4)	0.80050 (9)	0.2365 (3)	0.0555 (6)
C3	0.5587 (4)	0.78096 (9)	0.3395 (3)	0.0573 (6)
C4	0.4031 (4)	0.82090 (9)	0.3971 (2)	0.0526 (6)
C5	0.2448 (3)	0.92534 (9)	0.4000 (2)	0.0518 (6)
C6	0.2542 (4)	0.98292 (9)	0.3460 (3)	0.0563 (6)
C7	0.4273 (4)	1.00048 (9)	0.2448 (2)	0.0549 (6)
C8	0.5876 (3)	0.96036 (9)	0.1949 (2)	0.0500 (6)
C9	0.5757 (3)	0.90021 (7)	0.24515 (19)	0.0412 (5)
C10	0.4060 (3)	0.88192 (8)	0.3504 (2)	0.0426 (5)
Cl	0.09830 (8)	0.64588 (2)	0.35498 (5)	0.0476 (2)
O1	0.0144 (3)	0.59498 (7)	0.4403 (2)	0.0766 (6)
O2	0.0794 (3)	0.69763 (7)	0.4590 (2)	0.0806 (7)
O3	−0.0501 (4)	0.65437 (11)	0.1949 (2)	0.1001 (9)
O4	0.3474 (3)	0.63731 (7)	0.3344 (2)	0.0735 (6)
H1	0.819 (4)	0.8691 (10)	0.127 (3)	0.055 (6)*
H2	0.821 (4)	0.7767 (10)	0.191 (3)	0.064 (6)*
H3	0.561 (5)	0.7424 (12)	0.364 (3)	0.080 (8)*
H4	0.295 (4)	0.8091 (9)	0.467 (3)	0.055 (6)*
H5	0.129 (4)	0.9120 (9)	0.473 (3)	0.060 (6)*
H6	0.145 (4)	1.0124 (11)	0.380 (3)	0.068 (6)*
H7	0.432 (4)	1.0391 (11)	0.217 (3)	0.067 (7)*
H8	0.703 (4)	0.9714 (9)	0.127 (3)	0.056 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0482 (8)	0.0593 (9)	0.0420 (8)	0.0028 (7)	0.0133 (7)	0.0020 (6)
C2	0.0586 (11)	0.0546 (11)	0.0521 (11)	0.0102 (9)	0.0059 (8)	−0.0031 (8)
C3	0.0668 (12)	0.0443 (10)	0.0581 (11)	−0.0019 (9)	0.0021 (9)	0.0067 (8)
C4	0.0540 (10)	0.0547 (11)	0.0492 (10)	−0.0086 (8)	0.0092 (8)	0.0073 (8)
C5	0.0499 (10)	0.0631 (11)	0.0442 (9)	−0.0014 (8)	0.0131 (8)	−0.0047 (8)
C6	0.0600 (11)	0.0554 (11)	0.0523 (10)	0.0088 (9)	0.0058 (9)	−0.0077 (8)
C7	0.0651 (12)	0.0439 (10)	0.0520 (10)	−0.0020 (8)	−0.0016 (9)	0.0021 (8)
C8	0.0525 (10)	0.0540 (10)	0.0430 (9)	−0.0086 (8)	0.0062 (8)	0.0072 (7)
C9	0.0413 (8)	0.0474 (9)	0.0339 (7)	−0.0021 (6)	0.0036 (6)	0.0007 (6)
C10	0.0426 (8)	0.0484 (9)	0.0363 (8)	−0.0046 (7)	0.0052 (6)	0.0007 (6)
Cl	0.0501 (3)	0.0465 (3)	0.0488 (3)	0.0042 (2)	0.0155 (2)	0.0010 (2)
O1	0.0883 (11)	0.0560 (9)	0.0921 (12)	−0.0146 (8)	0.0345 (9)	0.0052 (8)
O2	0.1059 (13)	0.0565 (9)	0.0892 (12)	−0.0006 (8)	0.0449 (10)	−0.0171 (8)
O3	0.0926 (14)	0.1481 (19)	0.0557 (10)	0.0361 (12)	0.0001 (9)	0.0074 (11)
O4	0.0551 (9)	0.0696 (10)	0.1013 (13)	0.0066 (7)	0.0291 (8)	0.0006 (8)

Geometric parameters (Å, º)

Cl—O1	1.4400 (15)	C6—C7	1.402 (3)
Cl—O2	1.4377 (15)	C7—C8	1.361 (3)
Cl—O3	1.4134 (18)	C8—C9	1.407 (3)
Cl—O4	1.4179 (15)	C9—C10	1.415 (2)
N1—C2	1.324 (3)	C2—H2	0.89 (2)
N1—C9	1.371 (2)	C3—H3	0.88 (3)
N1—H1	0.83 (2)	C4—H4	0.92 (2)
C2—C3	1.378 (3)	C5—H5	0.98 (2)
C3—C4	1.366 (3)	C6—H6	0.96 (2)
C4—C10	1.414 (3)	C7—H7	0.89 (2)
C5—C6	1.360 (3)	C8—H8	0.93 (2)
C5—C10	1.413 (3)
O1—Cl—O2	107.55 (9)	N1—C9—C10	118.08 (15)
O1—Cl—O3	110.68 (12)	C4—C10—C5	123.55 (16)
O1—Cl—O4	109.77 (10)	C4—C10—C9	118.20 (16)
O2—Cl—O3	109.31 (12)	C5—C10—C9	118.24 (16)
O2—Cl—O4	109.75 (10)	N1—C2—H2	115.2 (15)
O3—Cl—O4	109.74 (11)	C3—C2—H2	124.2 (15)
C2—N1—C9	123.12 (17)	C4—C3—H3	123.3 (17)
C2—N1—H1	120.6 (15)	C2—C3—H3	117.0 (17)
C9—N1—H1	116.2 (15)	C3—C4—H4	121.4 (13)
N1—C2—C3	120.56 (19)	C10—C4—H4	118.3 (13)
C2—C3—C4	119.68 (19)	C6—C5—H5	122.7 (12)
C3—C4—C10	120.36 (18)	C10—C5—H5	117.2 (12)
C6—C5—C10	120.11 (17)	C7—C6—H6	119.1 (14)
C5—C6—C7	120.82 (19)	C5—C6—H6	120.1 (14)
C6—C7—C8	121.17 (18)	C6—C7—H7	117.7 (15)
C7—C8—C9	118.84 (16)	C8—C7—H7	121.1 (15)
N1—C9—C8	121.14 (15)	C9—C8—H8	119.1 (13)
C8—C9—C10	120.77 (15)	C7—C8—H8	122.0 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.83 (2)	2.13 (2)	2.958 (2)	172 (2)
N1—H1···O2^i	0.83 (2)	2.59 (2)	3.156 (2)	127 (2)
C2—H2···O2^i	0.89 (2)	2.58 (2)	3.200 (3)	128 (2)
C5—H5···O3^ii	0.98 (2)	2.62 (2)	3.550 (3)	158 (2)
C7—H7···O4^iii	0.89 (2)	2.57 (2)	3.395 (3)	154 (2)

Symmetry codes: (i) x+1, −y+3/2, z−1/2; (ii) x, −y+3/2, z+1/2; (iii) −x+1, y+1/2, −z+1/2.