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In the cation of the title compound, C7H13N6O+·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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804030545/rz6022sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804030545/rz6022Isup2.hkl
Contains datablock I

CCDC reference: 259854

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](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

Computing details top

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+·ClDx = 1.285 Mg m3
Mr = 232.68Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3Cell parameters from 40554 reflections
Hall symbol: -R 3θ = 1.0–27.5°
a = 27.3044 (5) ŵ = 0.31 mm1
c = 8.3804 (2) ÅT = 150 K
V = 5410.79 (19) Å3Needle, colourless
Z = 180.42 × 0.24 × 0.21 mm
F(000) = 2196
Data collection top
Nonius KappaCCD
diffractometer
2083 reflections with I > 2σ(I)
Radiation source: rotating anodeRint = 0.049
Graphite monochromatorθmax = 27.5°, θmin = 1.5°
φ and ω scansh = 3534
18411 measured reflectionsk = 2335
2757 independent reflectionsl = 1010
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-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 parametersΔρmax = 0.25 e Å3
4 restraintsΔρmin = 0.33 e Å3
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
xyzUiso*/Ueq
N10.23172 (6)0.27401 (6)0.08880 (17)0.0272 (3)
N20.20154 (6)0.30379 (6)0.10483 (17)0.0257 (3)
H20.2288 (7)0.3419 (6)0.115 (2)0.031*
C30.16738 (7)0.29436 (7)0.0370 (2)0.0257 (4)
H30.14990.31890.02940.031*
N40.19776 (6)0.30675 (6)0.18688 (17)0.0274 (3)
H40.2160 (8)0.3442 (6)0.194 (2)0.033*
N50.23566 (6)0.28475 (6)0.18744 (17)0.0276 (3)
C60.24780 (7)0.26384 (7)0.0552 (2)0.0246 (4)
C70.24061 (8)0.25209 (8)0.2367 (2)0.0336 (4)
H7A0.25970.23050.21430.050*
H7B0.26410.28360.30840.050*
H7C0.20400.22730.28750.050*
C80.24335 (9)0.26677 (8)0.3450 (2)0.0354 (4)
H8A0.22570.22550.34720.053*
H8B0.22570.27890.42580.053*
H8C0.28380.28390.36770.053*
O90.27229 (5)0.23607 (5)0.06602 (15)0.0321 (3)
N110.09525 (6)0.20248 (6)0.09020 (18)0.0277 (3)
H110.1018 (8)0.2150 (8)0.1852 (19)0.033*
C120.12066 (7)0.23410 (7)0.0368 (2)0.0250 (4)
N130.09534 (6)0.20318 (6)0.16540 (18)0.0288 (3)
H130.1057 (8)0.2132 (9)0.2595 (19)0.035*
C140.05220 (8)0.15042 (8)0.1186 (2)0.0365 (4)
H140.02740.12030.18650.044*
C150.05238 (8)0.15031 (8)0.0417 (2)0.0346 (4)
H150.02760.11990.10900.042*
Cl10.226068 (19)0.125922 (19)0.46110 (5)0.03437 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0315 (8)0.0347 (8)0.0214 (7)0.0211 (7)0.0002 (6)0.0034 (6)
N20.0267 (7)0.0273 (8)0.0242 (7)0.0144 (7)0.0003 (6)0.0064 (6)
C30.0284 (9)0.0295 (9)0.0240 (9)0.0179 (8)0.0014 (7)0.0032 (7)
N40.0334 (8)0.0273 (8)0.0260 (8)0.0185 (7)0.0043 (6)0.0015 (6)
N50.0306 (8)0.0352 (8)0.0215 (7)0.0199 (7)0.0038 (6)0.0015 (6)
C60.0189 (8)0.0236 (8)0.0262 (9)0.0069 (7)0.0017 (7)0.0029 (7)
C70.0379 (10)0.0411 (11)0.0257 (9)0.0228 (9)0.0002 (8)0.0012 (8)
C80.0412 (11)0.0457 (11)0.0242 (9)0.0253 (9)0.0047 (8)0.0039 (8)
O90.0340 (7)0.0364 (7)0.0317 (7)0.0219 (6)0.0047 (5)0.0005 (5)
N110.0279 (8)0.0342 (8)0.0218 (8)0.0161 (7)0.0003 (6)0.0024 (6)
C120.0248 (8)0.0311 (9)0.0235 (9)0.0172 (8)0.0003 (7)0.0019 (7)
N130.0296 (8)0.0332 (8)0.0222 (8)0.0145 (7)0.0010 (6)0.0015 (6)
C140.0286 (10)0.0351 (10)0.0374 (11)0.0097 (8)0.0055 (8)0.0048 (8)
C150.0275 (9)0.0352 (10)0.0353 (11)0.0112 (8)0.0002 (8)0.0019 (8)
Cl10.0404 (3)0.0392 (3)0.0225 (2)0.0191 (2)0.00008 (18)0.00128 (18)
Geometric parameters (Å, º) top
N1—N21.4244 (19)C7—H7B0.9800
N1—C71.449 (2)C7—H7C0.9800
N2—C31.452 (2)C8—H8A0.9800
N2—H20.933 (14)C8—H8B0.9800
C3—N41.449 (2)C8—H8C0.9800
C3—C121.495 (2)N11—C121.327 (2)
C3—H31.0000N11—H110.849 (15)
N4—N51.433 (2)C12—N131.330 (2)
N4—H40.889 (14)N13—C141.385 (2)
N5—C61.361 (2)N13—H130.836 (15)
N5—C81.460 (2)C14—C151.344 (3)
C6—N11.359 (2)C14—H140.9500
C6—O91.240 (2)C15—N111.378 (2)
C7—H7A0.9800C15—H150.9500
C6—N1—N2122.58 (14)N1—C7—H7C109.5
C6—N1—C7122.49 (15)H7A—C7—H7C109.5
N2—N1—C7114.81 (13)H7B—C7—H7C109.5
N1—N2—C3108.98 (12)N5—C8—H8A109.5
N1—N2—H2106.3 (11)N5—C8—H8B109.5
C3—N2—H2110.9 (12)H8A—C8—H8B109.5
N2—C3—N4115.22 (14)N5—C8—H8C109.5
N2—C3—C12108.26 (14)H8A—C8—H8C109.5
N4—C3—C12109.38 (14)H8B—C8—H8C109.5
N4—C3—H3107.9C15—N11—C12109.49 (15)
N2—C3—H3107.9C12—N11—H11123.7 (14)
C12—C3—H3107.9C15—N11—H11126.2 (14)
C3—N4—N5110.73 (13)N11—C12—N13107.47 (16)
N5—N4—H4112.0 (13)N11—C12—C3126.71 (16)
C3—N4—H4104.9 (13)N13—C12—C3125.76 (16)
N4—N5—C6123.47 (13)C12—N13—C14109.44 (15)
N4—N5—C8113.53 (13)C12—N13—H13125.0 (14)
C6—N5—C8119.28 (14)C14—N13—H13125.4 (14)
N5—C6—N1117.76 (15)N13—C14—C15106.44 (16)
N5—C6—O9121.05 (15)C15—C14—H14126.8
N1—C6—O9121.19 (16)N13—C14—H14126.8
N1—C7—H7A109.5C14—C15—N11107.15 (16)
N1—C7—H7B109.5C14—C15—H15126.4
H7A—C7—H7B109.5N11—C15—H15126.4
C6—N1—N2—C329.5 (2)N4—N5—C6—N112.7 (2)
C7—N1—N2—C3146.52 (15)C8—N5—C6—N1169.58 (15)
N1—N2—C3—N453.07 (18)C15—N11—C12—N130.54 (19)
N1—N2—C3—C1269.72 (16)C15—N11—C12—C3176.83 (16)
N2—C3—N4—N544.03 (19)N4—C3—C12—N11157.95 (16)
C12—C3—N4—N578.16 (17)N2—C3—C12—N1131.7 (2)
C3—N4—N5—C610.2 (2)N4—C3—C12—N1325.1 (2)
C3—N4—N5—C8147.84 (15)N2—C3—C12—N13151.42 (16)
N2—N1—C6—O9177.43 (15)N11—C12—N13—C140.5 (2)
C7—N1—C6—O91.7 (3)C3—C12—N13—C14176.91 (16)
N2—N1—C6—N52.0 (2)C12—N13—C14—C150.3 (2)
C7—N1—C6—N5177.72 (15)N13—C14—C15—N110.1 (2)
N4—N5—C6—O9166.69 (15)C12—N11—C15—C140.4 (2)
C8—N5—C6—O99.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O9i0.93 (1)2.12 (2)2.8857 (19)139 (2)
N4—H4···Cl1i0.89 (1)2.50 (2)3.3170 (15)154 (2)
N11—H11···Cl1ii0.85 (2)2.34 (2)3.1636 (15)165 (2)
N13—H13···Cl1iii0.84 (2)2.38 (2)3.1817 (16)160 (2)
Symmetry codes: (i) x+y+1/3, x+2/3, z1/3; (ii) xy, x, z; (iii) xy, x, z+1.
 

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