The crystal structure of the title compound, C
6H
6N
3+·ClO
4−·H
2O, 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.
Supporting information
CCDC reference: 647197
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.037
- wR factor = 0.105
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
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
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
top
Crystal data top
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) Å3 | |
Data collection top
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 top
Refinement on F2 | Secondary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0555P)2 + 0.1556P] where P = (Fo2 + 2Fc2)/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+0.001xFc2λ3/sin(2θ)]-1/4 |
18 constraints | Extinction coefficient: 0.45 (2) |
Primary atom site location: structure-invariant direct methods | |
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 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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···O2i | 0.75 (3) | 2.32 (3) | 2.920 (3) | 139 (3) |
N3—H3···O4ii | 0.75 (3) | 2.54 (3) | 3.027 (3) | 124 (2) |
O1—H12···O2iii | 0.82 | 2.21 | 2.972 (3) | 154 |
O1—H11···O3iv | 0.82 | 2.18 | 2.943 (3) | 155 |
O1—H11···O3v | 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. |