Pyridazinium perchlorate

The crystal structure of the title compound, C₄H₅N₂⁺·ClO₄⁻, consists of cations and anions linked by N—H...O and C—H...O hydrogen bonds, resulting in a two-dimensional network structure.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.031
• wR factor = 0.084
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



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

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   0 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 2003); molecular graphics: SHELXTL and Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2003).

Pyridazinium perchlorate

Crystal data

C4H5N2^+·ClO4^−	F(000) = 368
Mr = 180.55	Dx = 1.762 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6491 reflections
a = 5.27604 (10) Å	θ = 2.7–29.1°
b = 8.62700 (16) Å	µ = 0.53 mm^−1
c = 15.0058 (3) Å	T = 294 K
β = 94.8879 (19)°	Prism, colourless
V = 680.53 (2) Å^3	0.50 × 0.45 × 0.40 mm
Z = 4

Data collection

Kuma KM-4 CCD diffractometer	1561 independent reflections
Radiation source: CX-Mo12x0.4-S Seifert Mo tube	1473 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
Detector resolution: 8.2356 pixels mm^-1	θmax = 27.5°, θmin = 2.7°
ω scans	h = −6→6
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −11→10
Tmin = 0.779, Tmax = 0.817	l = −19→19
8856 measured 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)] = 0.031	All H-atom parameters refined
wR(F^2) = 0.084	w = 1/[σ^2(Fo^2) + (0.038P)^2 + 0.4195P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
1561 reflections	Δρmax = 0.41 e Å^−3
121 parameters	Δρmin = −0.30 e Å^−3
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2Λ^3/sin(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.066 (4)

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
Cl	0.09166 (7)	0.23185 (4)	0.63927 (2)	0.03117 (16)
O1	−0.1739 (2)	0.27178 (16)	0.63799 (10)	0.0456 (3)
O4	0.1310 (3)	0.1400 (2)	0.56270 (10)	0.0647 (5)
O2	0.1610 (3)	0.1421 (2)	0.71778 (10)	0.0647 (5)
O3	0.2399 (3)	0.36921 (18)	0.64092 (15)	0.0759 (6)
N2	1.0410 (3)	0.15729 (17)	0.94701 (10)	0.0402 (3)
C5	0.6820 (3)	0.3130 (2)	0.83451 (11)	0.0376 (4)
C4	0.8859 (3)	0.3897 (2)	0.87512 (12)	0.0383 (4)
N1	0.8404 (3)	0.08858 (17)	0.90472 (11)	0.0396 (3)
C3	1.0611 (3)	0.3067 (2)	0.93117 (12)	0.0375 (4)
C6	0.6635 (3)	0.1557 (2)	0.85107 (12)	0.0379 (4)
H3	1.201 (4)	0.355 (3)	0.9602 (14)	0.050 (6)*
H4	0.910 (4)	0.491 (3)	0.8680 (13)	0.049 (6)*
H5	0.560 (4)	0.360 (3)	0.7945 (15)	0.060 (7)*
H6	0.537 (4)	0.089 (3)	0.8273 (14)	0.047 (5)*
H1	0.832 (5)	−0.001 (3)	0.9106 (16)	0.061 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.0302 (2)	0.0270 (2)	0.0356 (2)	0.00262 (12)	−0.00157 (14)	−0.00094 (13)
O1	0.0326 (7)	0.0486 (8)	0.0547 (8)	0.0088 (5)	−0.0021 (5)	0.0020 (6)
O4	0.0716 (10)	0.0699 (10)	0.0529 (8)	0.0169 (8)	0.0072 (7)	−0.0219 (8)
O2	0.0662 (10)	0.0736 (11)	0.0512 (8)	0.0186 (8)	−0.0134 (7)	0.0178 (8)
O3	0.0533 (9)	0.0395 (8)	0.1359 (17)	−0.0137 (7)	0.0142 (9)	−0.0053 (9)
N2	0.0397 (7)	0.0341 (7)	0.0443 (8)	0.0029 (6)	−0.0114 (6)	−0.0005 (6)
C5	0.0382 (8)	0.0383 (9)	0.0355 (8)	0.0068 (7)	−0.0016 (6)	0.0053 (7)
C4	0.0454 (9)	0.0268 (8)	0.0430 (9)	−0.0012 (6)	0.0053 (7)	0.0028 (7)
N1	0.0427 (8)	0.0248 (7)	0.0494 (8)	−0.0016 (6)	−0.0073 (6)	0.0020 (6)
C3	0.0358 (8)	0.0351 (8)	0.0407 (9)	−0.0039 (7)	−0.0028 (6)	−0.0062 (7)
C6	0.0344 (8)	0.0366 (9)	0.0412 (9)	−0.0038 (6)	−0.0052 (6)	−0.0018 (7)

Geometric parameters (Å, º)

N1—N2	1.326 (2)	N1—H1	0.78 (3)
N1—C6	1.314 (2)	C3—H3	0.92 (2)
N2—C3	1.316 (2)	C6—H6	0.93 (2)
C3—C4	1.394 (2)	Cl—O1	1.4411 (13)
C4—C5	1.362 (2)	Cl—O2	1.4310 (14)
C5—C6	1.385 (3)	Cl—O3	1.4190 (15)
C5—H5	0.93 (2)	Cl—O4	1.4252 (14)
C4—H4	0.89 (2)
N1—N2—C3	115.12 (14)	C5—C4—H4	122.5 (13)
N2—N1—C6	126.32 (15)	C3—C4—H4	118.9 (13)
N2—N1—H1	116.1 (18)	C6—N1—H1	117.5 (18)
N1—C6—C5	118.99 (16)	C4—C3—H3	121.1 (14)
N1—C6—H6	114.3 (13)	C5—C6—H6	126.7 (13)
N2—C3—C4	123.54 (15)	O1—Cl—O2	108.68 (9)
N2—C3—H3	115.4 (14)	O1—Cl—O3	109.54 (9)
C3—C4—C5	118.56 (16)	O1—Cl—O4	109.28 (9)
C4—C5—C6	117.45 (15)	O2—Cl—O3	109.61 (12)
C4—C5—H5	123.7 (15)	O2—Cl—O4	108.57 (10)
C6—C5—H5	118.8 (15)	O3—Cl—O4	111.12 (12)
C6—N1—N2—C3	−1.1 (3)	N2—C3—C4—C5	0.2 (3)
N2—N1—C6—C5	0.7 (3)	C3—C4—C5—C6	−0.7 (2)
N1—N2—C3—C4	0.6 (3)	C4—C5—C6—N1	0.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.78 (3)	2.23 (3)	2.925 (2)	149 (2)
N1—H1···N2^ii	0.78 (3)	2.57 (2)	3.099 (2)	127 (2)
C6—H6···O2	0.93 (2)	2.51 (2)	3.184 (2)	130 (2)
C6—H6···O3^i	0.93 (2)	2.47 (2)	3.271 (2)	145.1 (18)

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