Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807013542/fb2047sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807013542/fb2047Isup2.hkl |
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).
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 |
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 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 |
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. |
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) |
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) |
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) |
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. |
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