In the cation of the title compound, C
7H
13N
6O
+·Cl
−, the presence of an
sp3-hybridized C atom at the point of attachment of the imidazolyl substituent leads to a conformation for the tetrazane ring that is intermediate between a screw boat and an envelope. The crystal structure of (I) consists of a three-dimensional network of N—H
O and N—H
Cl hydrogen-bonded cations and anions that is perforated by channels filled with disordered methanol solvent molecules.
Supporting information
CCDC reference: 259854
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.002 Å
- R factor = 0.040
- wR factor = 0.106
- Data-to-parameter ratio = 18.4
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT601_ALERT_2_A Structure Contains Solvent Accessible VOIDS of . 253.00 A 3
| Author Response: see _publ_section_exptl_refinement
|
1 ALERT level A = In general: serious problem
0 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
Data collection: COLLECT (Nonius, 1998); cell refinement: HKL-2000 (Otwinowski & Minor, 1997); data reduction: HKL-2000; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
[1,5-Dimethyl-6-oxo-1,2,4,5-tetrazinan-3-yl]imidazolium chloride
top
Crystal data top
C7H13N6O+·Cl− | Dx = 1.285 Mg m−3 |
Mr = 232.68 | Mo Kα radiation, λ = 0.71073 Å |
Trigonal, R3 | Cell parameters from 40554 reflections |
Hall symbol: -R 3 | θ = 1.0–27.5° |
a = 27.3044 (5) Å | µ = 0.31 mm−1 |
c = 8.3804 (2) Å | T = 150 K |
V = 5410.79 (19) Å3 | Needle, colourless |
Z = 18 | 0.42 × 0.24 × 0.21 mm |
F(000) = 2196 | |
Data collection top
Nonius KappaCCD diffractometer | 2083 reflections with I > 2σ(I) |
Radiation source: rotating anode | Rint = 0.049 |
Graphite monochromator | θmax = 27.5°, θmin = 1.5° |
φ and ω scans | h = −35→34 |
18411 measured reflections | k = −23→35 |
2757 independent reflections | l = −10→10 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0525P)2 + 3.583P] where P = (Fo2 + 2Fc2)/3 |
2757 reflections | (Δ/σ)max = 0.001 |
150 parameters | Δρmax = 0.25 e Å−3 |
4 restraints | Δρmin = −0.33 e Å−3 |
Special details top
Experimental. calc SQUEEZE (vol 712.9 Å3, 262 elec) |
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 of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) 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 | 0.23172 (6) | 0.27401 (6) | −0.08880 (17) | 0.0272 (3) | |
N2 | 0.20154 (6) | 0.30379 (6) | −0.10483 (17) | 0.0257 (3) | |
H2 | 0.2288 (7) | 0.3419 (6) | −0.115 (2) | 0.031* | |
C3 | 0.16738 (7) | 0.29436 (7) | 0.0370 (2) | 0.0257 (4) | |
H3 | 0.1499 | 0.3189 | 0.0294 | 0.031* | |
N4 | 0.19776 (6) | 0.30675 (6) | 0.18688 (17) | 0.0274 (3) | |
H4 | 0.2160 (8) | 0.3442 (6) | 0.194 (2) | 0.033* | |
N5 | 0.23566 (6) | 0.28475 (6) | 0.18744 (17) | 0.0276 (3) | |
C6 | 0.24780 (7) | 0.26384 (7) | 0.0552 (2) | 0.0246 (4) | |
C7 | 0.24061 (8) | 0.25209 (8) | −0.2367 (2) | 0.0336 (4) | |
H7A | 0.2597 | 0.2305 | −0.2143 | 0.050* | |
H7B | 0.2641 | 0.2836 | −0.3084 | 0.050* | |
H7C | 0.2040 | 0.2273 | −0.2875 | 0.050* | |
C8 | 0.24335 (9) | 0.26677 (8) | 0.3450 (2) | 0.0354 (4) | |
H8A | 0.2257 | 0.2255 | 0.3472 | 0.053* | |
H8B | 0.2257 | 0.2789 | 0.4258 | 0.053* | |
H8C | 0.2838 | 0.2839 | 0.3677 | 0.053* | |
O9 | 0.27229 (5) | 0.23607 (5) | 0.06602 (15) | 0.0321 (3) | |
N11 | 0.09525 (6) | 0.20248 (6) | −0.09020 (18) | 0.0277 (3) | |
H11 | 0.1018 (8) | 0.2150 (8) | −0.1852 (19) | 0.033* | |
C12 | 0.12066 (7) | 0.23410 (7) | 0.0368 (2) | 0.0250 (4) | |
N13 | 0.09534 (6) | 0.20318 (6) | 0.16540 (18) | 0.0288 (3) | |
H13 | 0.1057 (8) | 0.2132 (9) | 0.2595 (19) | 0.035* | |
C14 | 0.05220 (8) | 0.15042 (8) | 0.1186 (2) | 0.0365 (4) | |
H14 | 0.0274 | 0.1203 | 0.1865 | 0.044* | |
C15 | 0.05238 (8) | 0.15031 (8) | −0.0417 (2) | 0.0346 (4) | |
H15 | 0.0276 | 0.1199 | −0.1090 | 0.042* | |
Cl1 | 0.226068 (19) | 0.125922 (19) | 0.46110 (5) | 0.03437 (15) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0315 (8) | 0.0347 (8) | 0.0214 (7) | 0.0211 (7) | 0.0002 (6) | 0.0034 (6) |
N2 | 0.0267 (7) | 0.0273 (8) | 0.0242 (7) | 0.0144 (7) | −0.0003 (6) | 0.0064 (6) |
C3 | 0.0284 (9) | 0.0295 (9) | 0.0240 (9) | 0.0179 (8) | −0.0014 (7) | 0.0032 (7) |
N4 | 0.0334 (8) | 0.0273 (8) | 0.0260 (8) | 0.0185 (7) | −0.0043 (6) | −0.0015 (6) |
N5 | 0.0306 (8) | 0.0352 (8) | 0.0215 (7) | 0.0199 (7) | −0.0038 (6) | 0.0015 (6) |
C6 | 0.0189 (8) | 0.0236 (8) | 0.0262 (9) | 0.0069 (7) | −0.0017 (7) | 0.0029 (7) |
C7 | 0.0379 (10) | 0.0411 (11) | 0.0257 (9) | 0.0228 (9) | −0.0002 (8) | −0.0012 (8) |
C8 | 0.0412 (11) | 0.0457 (11) | 0.0242 (9) | 0.0253 (9) | −0.0047 (8) | 0.0039 (8) |
O9 | 0.0340 (7) | 0.0364 (7) | 0.0317 (7) | 0.0219 (6) | −0.0047 (5) | 0.0005 (5) |
N11 | 0.0279 (8) | 0.0342 (8) | 0.0218 (8) | 0.0161 (7) | −0.0003 (6) | 0.0024 (6) |
C12 | 0.0248 (8) | 0.0311 (9) | 0.0235 (9) | 0.0172 (8) | −0.0003 (7) | 0.0019 (7) |
N13 | 0.0296 (8) | 0.0332 (8) | 0.0222 (8) | 0.0145 (7) | 0.0010 (6) | 0.0015 (6) |
C14 | 0.0286 (10) | 0.0351 (10) | 0.0374 (11) | 0.0097 (8) | 0.0055 (8) | 0.0048 (8) |
C15 | 0.0275 (9) | 0.0352 (10) | 0.0353 (11) | 0.0112 (8) | −0.0002 (8) | −0.0019 (8) |
Cl1 | 0.0404 (3) | 0.0392 (3) | 0.0225 (2) | 0.0191 (2) | −0.00008 (18) | 0.00128 (18) |
Geometric parameters (Å, º) top
N1—N2 | 1.4244 (19) | C7—H7B | 0.9800 |
N1—C7 | 1.449 (2) | C7—H7C | 0.9800 |
N2—C3 | 1.452 (2) | C8—H8A | 0.9800 |
N2—H2 | 0.933 (14) | C8—H8B | 0.9800 |
C3—N4 | 1.449 (2) | C8—H8C | 0.9800 |
C3—C12 | 1.495 (2) | N11—C12 | 1.327 (2) |
C3—H3 | 1.0000 | N11—H11 | 0.849 (15) |
N4—N5 | 1.433 (2) | C12—N13 | 1.330 (2) |
N4—H4 | 0.889 (14) | N13—C14 | 1.385 (2) |
N5—C6 | 1.361 (2) | N13—H13 | 0.836 (15) |
N5—C8 | 1.460 (2) | C14—C15 | 1.344 (3) |
C6—N1 | 1.359 (2) | C14—H14 | 0.9500 |
C6—O9 | 1.240 (2) | C15—N11 | 1.378 (2) |
C7—H7A | 0.9800 | C15—H15 | 0.9500 |
| | | |
C6—N1—N2 | 122.58 (14) | N1—C7—H7C | 109.5 |
C6—N1—C7 | 122.49 (15) | H7A—C7—H7C | 109.5 |
N2—N1—C7 | 114.81 (13) | H7B—C7—H7C | 109.5 |
N1—N2—C3 | 108.98 (12) | N5—C8—H8A | 109.5 |
N1—N2—H2 | 106.3 (11) | N5—C8—H8B | 109.5 |
C3—N2—H2 | 110.9 (12) | H8A—C8—H8B | 109.5 |
N2—C3—N4 | 115.22 (14) | N5—C8—H8C | 109.5 |
N2—C3—C12 | 108.26 (14) | H8A—C8—H8C | 109.5 |
N4—C3—C12 | 109.38 (14) | H8B—C8—H8C | 109.5 |
N4—C3—H3 | 107.9 | C15—N11—C12 | 109.49 (15) |
N2—C3—H3 | 107.9 | C12—N11—H11 | 123.7 (14) |
C12—C3—H3 | 107.9 | C15—N11—H11 | 126.2 (14) |
C3—N4—N5 | 110.73 (13) | N11—C12—N13 | 107.47 (16) |
N5—N4—H4 | 112.0 (13) | N11—C12—C3 | 126.71 (16) |
C3—N4—H4 | 104.9 (13) | N13—C12—C3 | 125.76 (16) |
N4—N5—C6 | 123.47 (13) | C12—N13—C14 | 109.44 (15) |
N4—N5—C8 | 113.53 (13) | C12—N13—H13 | 125.0 (14) |
C6—N5—C8 | 119.28 (14) | C14—N13—H13 | 125.4 (14) |
N5—C6—N1 | 117.76 (15) | N13—C14—C15 | 106.44 (16) |
N5—C6—O9 | 121.05 (15) | C15—C14—H14 | 126.8 |
N1—C6—O9 | 121.19 (16) | N13—C14—H14 | 126.8 |
N1—C7—H7A | 109.5 | C14—C15—N11 | 107.15 (16) |
N1—C7—H7B | 109.5 | C14—C15—H15 | 126.4 |
H7A—C7—H7B | 109.5 | N11—C15—H15 | 126.4 |
| | | |
C6—N1—N2—C3 | −29.5 (2) | N4—N5—C6—N1 | 12.7 (2) |
C7—N1—N2—C3 | 146.52 (15) | C8—N5—C6—N1 | 169.58 (15) |
N1—N2—C3—N4 | 53.07 (18) | C15—N11—C12—N13 | 0.54 (19) |
N1—N2—C3—C12 | −69.72 (16) | C15—N11—C12—C3 | −176.83 (16) |
N2—C3—N4—N5 | −44.03 (19) | N4—C3—C12—N11 | −157.95 (16) |
C12—C3—N4—N5 | 78.16 (17) | N2—C3—C12—N11 | −31.7 (2) |
C3—N4—N5—C6 | 10.2 (2) | N4—C3—C12—N13 | 25.1 (2) |
C3—N4—N5—C8 | −147.84 (15) | N2—C3—C12—N13 | 151.42 (16) |
N2—N1—C6—O9 | 177.43 (15) | N11—C12—N13—C14 | −0.5 (2) |
C7—N1—C6—O9 | 1.7 (3) | C3—C12—N13—C14 | 176.91 (16) |
N2—N1—C6—N5 | −2.0 (2) | C12—N13—C14—C15 | 0.3 (2) |
C7—N1—C6—N5 | −177.72 (15) | N13—C14—C15—N11 | 0.1 (2) |
N4—N5—C6—O9 | −166.69 (15) | C12—N11—C15—C14 | −0.4 (2) |
C8—N5—C6—O9 | −9.8 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O9i | 0.93 (1) | 2.12 (2) | 2.8857 (19) | 139 (2) |
N4—H4···Cl1i | 0.89 (1) | 2.50 (2) | 3.3170 (15) | 154 (2) |
N11—H11···Cl1ii | 0.85 (2) | 2.34 (2) | 3.1636 (15) | 165 (2) |
N13—H13···Cl1iii | 0.84 (2) | 2.38 (2) | 3.1817 (16) | 160 (2) |
Symmetry codes: (i) −x+y+1/3, −x+2/3, z−1/3; (ii) x−y, x, −z; (iii) x−y, x, −z+1. |