Benzotriazolium perchlorate monohydrate

The crystal structure of the title compound, C₆H₆N₃⁺·ClO₄⁻·H₂O, consists of cations, anions and water mol­ecules linked by N—H...O and O—H...O hydrogen bonds into sheets of alternating R₄⁴(12) and R₆⁶(20) rings, which form chains running along the [10] direction.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.037
• wR factor = 0.105
• Data-to-parameter ratio = 12.7

checkCIF/PLATON results

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Alert level C
PLAT352_ALERT_3_C Short   N-H Bond (0.87A)   N3     -   H3     ...       0.75 Ang.

   0 ALERT level A = In general: serious problem
   0 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXTL (Sheldrick, 2001); molecular graphics: SHELXTL and Mercury (Macrae et al., 2006); software used to prepare material for publication: PLATON (Spek, 2003).

Benzotriazolium perchlorate monohydrate

Crystal data

C6H6N3^+·ClO4^−·H2O	Z = 2
Mr = 237.60	F(000) = 244
Triclinic, P1	Dx = 1.604 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4227 (2) Å	Cell parameters from 2865 reflections
b = 8.0524 (2) Å	θ = 3.2–29.6°
c = 8.8973 (3) Å	µ = 0.40 mm^−1
α = 74.023 (3)°	T = 298 K
β = 74.335 (3)°	Prism, colourless
γ = 87.246 (2)°	0.50 × 0.50 × 0.30 mm
V = 492.07 (3) Å^3

Data collection

Kuma KM-4 CCD diffractometer	1925 independent reflections
Radiation source: CX-Mo12x0.4-S Seifert Mo tube	1842 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 8.2356 pixels mm^-1	θmax = 26.0°, θmin = 3.2°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −9→9
Tmin = 0.827, Tmax = 0.893	l = −10→10
5415 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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.105	w = 1/[σ^2(Fo^2) + (0.0555P)^2 + 0.1556P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.001
1925 reflections	Δρmax = 0.26 e Å^−3
151 parameters	Δρmin = −0.32 e Å^−3
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
18 constraints	Extinction coefficient: 0.45 (2)
Primary atom site location: structure-invariant direct methods

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 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	0.6077 (2)	0.7487 (2)	0.1068 (2)	0.0540 (4)
H1	0.539 (4)	0.778 (3)	0.184 (4)	0.075 (8)*
N2	0.6810 (3)	0.8677 (2)	−0.0275 (2)	0.0638 (5)
N3	0.7791 (3)	0.7825 (2)	−0.1270 (2)	0.0582 (5)
H3	0.830 (4)	0.833 (4)	−0.211 (3)	0.075 (8)*
C4	0.8482 (3)	0.4673 (3)	−0.1179 (3)	0.0556 (5)
H4	0.9235	0.4812	−0.2230	0.077 (7)*
C5	0.8054 (3)	0.3082 (3)	−0.0087 (3)	0.0624 (6)
H5	0.8536	0.2108	−0.0407	0.074 (7)*
C6	0.6905 (3)	0.2862 (3)	0.1515 (3)	0.0646 (6)
H6	0.6657	0.1750	0.2206	0.076 (7)*
C7	0.6146 (3)	0.4228 (3)	0.2080 (3)	0.0575 (5)
H7	0.5400	0.4083	0.3133	0.072 (7)*
C8	0.6566 (2)	0.5855 (2)	0.0969 (2)	0.0444 (4)
C9	0.7706 (2)	0.6082 (2)	−0.0604 (2)	0.0450 (4)
O1	0.3697 (3)	0.8091 (3)	0.3658 (2)	0.0930 (7)
H11	0.3830	0.8770	0.4161	0.149 (17)*
H12	0.2594	0.7769	0.3986	0.115 (12)*
O2	0.0353 (3)	0.2147 (3)	0.4619 (2)	0.0855 (6)
O3	0.3183 (2)	0.1056 (2)	0.5049 (3)	0.0860 (6)
O4	0.0548 (3)	0.0865 (3)	0.7246 (2)	0.0929 (6)
O5	0.2057 (3)	0.3536 (2)	0.5799 (3)	0.0900 (6)
Cl	0.15385 (6)	0.19088 (6)	0.56963 (5)	0.0487 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0526 (9)	0.0525 (9)	0.0553 (10)	−0.0004 (7)	−0.0042 (8)	−0.0219 (8)
N2	0.0687 (11)	0.0448 (9)	0.0717 (12)	−0.0019 (8)	−0.0084 (9)	−0.0158 (8)
N3	0.0633 (10)	0.0494 (9)	0.0494 (10)	−0.0059 (8)	−0.0023 (8)	−0.0043 (8)
C4	0.0509 (10)	0.0655 (12)	0.0536 (11)	0.0060 (9)	−0.0104 (8)	−0.0255 (9)
C5	0.0632 (12)	0.0512 (11)	0.0823 (15)	0.0117 (9)	−0.0261 (11)	−0.0284 (10)
C6	0.0678 (13)	0.0463 (11)	0.0734 (14)	−0.0029 (9)	−0.0215 (11)	−0.0028 (10)
C7	0.0572 (11)	0.0576 (11)	0.0483 (11)	−0.0065 (9)	−0.0081 (9)	−0.0040 (9)
C8	0.0406 (8)	0.0484 (9)	0.0440 (9)	−0.0026 (7)	−0.0093 (7)	−0.0139 (7)
C9	0.0423 (9)	0.0474 (9)	0.0433 (9)	−0.0018 (7)	−0.0094 (7)	−0.0104 (7)
O1	0.0596 (11)	0.1402 (19)	0.0946 (14)	0.0028 (11)	−0.0046 (9)	−0.0726 (14)
O2	0.0825 (12)	0.1069 (14)	0.0670 (11)	−0.0006 (10)	−0.0290 (9)	−0.0144 (10)
O3	0.0620 (10)	0.0776 (11)	0.1139 (15)	0.0121 (8)	0.0004 (9)	−0.0440 (11)
O4	0.1075 (15)	0.0970 (14)	0.0490 (9)	−0.0135 (11)	0.0056 (9)	−0.0024 (9)
O5	0.0955 (13)	0.0663 (11)	0.1140 (16)	−0.0030 (9)	−0.0146 (11)	−0.0463 (11)
Cl	0.0482 (3)	0.0499 (3)	0.0437 (3)	0.00127 (18)	−0.00339 (19)	−0.01428 (19)

Geometric parameters (Å, º)

N1—N2	1.308 (3)	C6—C7	1.368 (3)
N1—C8	1.367 (3)	C6—H6	0.93
N1—H1	0.82 (3)	C7—C8	1.397 (3)
N2—N3	1.312 (3)	C7—H7	0.93
N3—C9	1.362 (3)	C8—C9	1.394 (2)
N3—H3	0.75 (3)	O1—H11	0.82
C4—C5	1.369 (3)	O1—H12	0.82
C4—C9	1.407 (3)	O2—Cl	1.4378 (18)
C4—H4	0.93	O3—Cl	1.4319 (16)
C5—C6	1.418 (3)	O4—Cl	1.4218 (17)
C5—H5	0.93	O5—Cl	1.4164 (17)
N2—N1—C8	112.87 (17)	C6—C7—H7	122.2
N2—N1—H1	119.2 (19)	C8—C7—H7	122.2
C8—N1—H1	127.9 (19)	N1—C8—C9	104.75 (16)
N1—N2—N3	104.84 (16)	N1—C8—C7	132.81 (18)
N2—N3—C9	113.31 (17)	C9—C8—C7	122.44 (18)
N2—N3—H3	118 (2)	N3—C9—C8	104.23 (16)
C9—N3—H3	129 (2)	N3—C9—C4	134.02 (18)
C5—C4—C9	115.45 (19)	C8—C9—C4	121.75 (17)
C5—C4—H4	122.3	H1—O1—H11	125.5
C9—C4—H4	122.3	H1—O1—H12	126.3
C4—C5—C6	122.48 (19)	H11—O1—H12	106.7
C4—C5—H5	118.8	O3—Cl—O2	108.14 (12)
C6—C5—H5	118.8	O4—Cl—O2	108.51 (12)
C7—C6—C5	122.3 (2)	O5—Cl—O2	109.78 (13)
C7—C6—H6	118.9	O4—Cl—O3	110.04 (13)
C5—C6—H6	118.9	O5—Cl—O3	109.37 (11)
C6—C7—C8	115.58 (19)	O5—Cl—O4	110.94 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.82 (3)	1.83 (3)	2.646 (2)	171 (3)
N3—H3···O2^i	0.75 (3)	2.32 (3)	2.920 (3)	139 (3)
N3—H3···O4^ii	0.75 (3)	2.54 (3)	3.027 (3)	124 (2)
O1—H12···O2^iii	0.82	2.21	2.972 (3)	154
O1—H11···O3^iv	0.82	2.18	2.943 (3)	155
O1—H11···O3^v	0.82	2.52	3.031 (3)	121

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1, y+1, z−1; (iii) −x, −y+1, −z+1; (iv) x, y+1, z; (v) −x+1, −y+1, −z+1.