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In the title complex, the 1:1 ionic adduct of hexa­methyl­enetetraminium and 2,4,6-tri­nitro­phenolate, C6H13N4+·­C6H2N3O7, the cation acts as a donor for bifurcated hydrogen bonds to the O atoms of the phenolate and one of the nitro groups of the 2,4,6-tri­nitro­phenolate anion. The crystal structure is built from sheets of cations and anions, and is stabilized by intermolecular C—H...O and C—H...π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101018571/ln1125sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101018571/ln1125Isup2.hkl
Contains datablock I

CCDC reference: 180171

Comment top

The crystal structures of the adducts of hexamethylenetetramine (HMT) and mono-, di-, or tri-phenol derivatives have been investigated intensively (Jordan & Mak, 1970; Mak et al., 1977, 1978; Mahmoud & Wallwork, 1979; Coupar, Glidewell & Ferguson, 1997; Coupar, Ferguson et al., 1997; Ng et al., 2001; Usman et al., 2001). Although HMT usually acts as an acceptor of up to three O—H···N hydrogen bonds (Jordan & Mak, 1970; Mak et al., 1977, 1978; Mahmoud & Wallwork, 1979; Coupar, Glidewell & Ferguson, 1997; Coupar, Ferguson et al., 1997), or partially acts as a hydrogen bond donor with 4-nitrophenol (Ng et al., 2001), recently we have shown that HMT can also act solely as an N—H···O hydrogen donor in the presence of 2,4-dinitrophenol (Usman et al., 2001). In this HMT-2,4-dinitrophenol complex, the phenolic H atom is transferred to the HMT. This H-atom transfer process occurs because 2,4-dinitrophenol is a stronger acid than the other phenols investigated. This unusual behaviour of HMT in the solid state is of interest, and led us to the title adduct where 2,4,6-trinitrophenol (TNP) also acts as a stronger acid.

Scheme 1

In the title complex, the TNP also transfers an H atom from the hydroxy group to the HMT moiety to form the 2,4,6-trinitrophenolate anion (TNP-), making the HMT positively charged.

The bond lengths and angles (Table 1) within the hexamethylenetetraminium cation (HMT+) are comparable with those of HMT+ in the 143 K polymorph of hexamethylenetetraminium-2,4-dinitrophenolate (Usman et al., 2001), while those within the TNP- anion are comparable with those of TNP- in potassium- and ammonium-2,4,6-trinitrophenolate (Maartmann-Moe, 1969). For instance, in the title complex the mean N—O bond length [1.224 (5) Å] and the C—O bond length agree with the mean N—C and C—O bond lengths in the two 2,4,6-trinitrophenolate derivatives reported by Maartmann-Moe (1969) [N—C 1.224 (6) Å and C—O 1.241 (7) Å].

In the HMT+ cation, the N—C bond distances around the N4 atom are elongated due to the positive charge localized on the protonated N4 atom. The N4—C7, N4—C8 and N4—C9 bond distances [mean value of 1.518 (2) Å] are equivalent to the length of the typical N—C single bond in the trimethylammonium ion (Allen et al., 1987). The protonated N4 atom also slightly affects the π-electron distribution in the surrounding atoms, which can be seen in the shortening by about 0.03 Å of the N5—C7, N6—C8, and N7—C9 bond distances compared with the other two N5—C, N6—C and N7—C bonds.

In the title adduct, the TNP- anion is nearly planar, with the nitro groups slightly twisted about their C—N bonds so that the angles between the aromatic ring plane and those of the CNO2 groupings containing N1, N2 and N3 are 11.06 (1), 7.96 (9) and 5.46 (10)°, respectively. The nitro-O atoms deviate from the aromatic ring plane by 0.287 (2) O2, -0.114 (2) O3, -0.307 (1) O4, -0.062 (2) O5, 0.175 (2) O6 and -0.017 (2) Å O7. For the HMT+ cation, all of the six-membered NCNCNC rings adopt a chair conformation, as shown by their puckering parameters (Cremer & Pople, 1975) (see Table 3).

The crystal structure of the title adduct is built from sheets of HMT+ cations and separate sheets of TNP- anions stacked alternately along the a axis. The HMT+ cation acts as an N—H···O hydrogen bond donor and forms bifurcated interionic hydrogen bonds with both the phenolate-O atom and a nitro-O atom of the same adjacent TNP- anion (Table 2). These interactions link the HMT+ and TNP- ions into ion pairs. Interionic C12—H12A···O7 and C12—H12B···O4 interactions interconnect the ion pairs into infinite two dimensional networks which lie perpendicular to the c axis (Fig. 2). An interionic C5—H5···π interaction involving the centroid of the aromatic ring of the TNP- anion was also observed (Table 2).

Experimental top

1.40 g (10 mmol) of hexamethylenetetramine and 2.29 g (10 mmol) of 2,4,6-trinitrophenol were thoroughly mixed and then dissolved in 50 ml of acetone with drops of water. The mixture was warmed until a clear solution was obtained. The solution was filtered off and left to evaporate slowly in air. Yellow single crystals suitable for X-ray data collection were obtained from the solution after a few days.

Refinement top

The H14N atom was located in a difference Fourier map and was refined freely as an isotropic atom. After checking for H atoms in the difference map, the positions of all remaining H atoms were geometrically idealized and allowed to ride on their parent atoms with C—H distances in the range 0.93–0.97 Å and fixed displacement parameters defined by Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Figures top
[Figure 1] Fig. 1. The structure of the title ionic adduct showing 50% probability displacement ellipsoids and the atom numbering scheme.
[Figure 2] Fig. 2. Packing diagram of the title ionic adduct viewed down the c axis. The dashed lines denote the interionic hydrogen bond interactions.
Hexamethylenetetramine-2,4,6-trinitrophenol top
Crystal data top
C6H13N4+·C6H2N3O7F(000) = 768
Mr = 369.31Dx = 1.661 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.4995 (2) ÅCell parameters from 6652 reflections
b = 6.6344 (1) Åθ = 3.2–28.3°
c = 18.6203 (2) ŵ = 0.14 mm1
β = 107.022 (1)°T = 183 K
V = 1476.48 (4) Å3Block, yellow
Z = 40.40 × 0.40 × 0.32 mm
Data collection top
Siemens SMART CCD area detector
diffractometer
3575 independent reflections
Radiation source: fine-focus sealed tube2697 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.069
Detector resolution: 8.33 pixels mm-1θmax = 28.3°, θmin = 3.2°
ω scansh = 1616
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 87
Tmin = 0.947, Tmax = 0.957l = 2416
8504 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.154 w = 1/[σ2(Fo2) + (0.0807P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max < 0.001
3575 reflectionsΔρmax = 0.43 e Å3
240 parametersΔρmin = 0.43 e Å3
0 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.033 (4)
Crystal data top
C6H13N4+·C6H2N3O7V = 1476.48 (4) Å3
Mr = 369.31Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.4995 (2) ŵ = 0.14 mm1
b = 6.6344 (1) ÅT = 183 K
c = 18.6203 (2) Å0.40 × 0.40 × 0.32 mm
β = 107.022 (1)°
Data collection top
Siemens SMART CCD area detector
diffractometer
3575 independent reflections
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
2697 reflections with I > 2σ(I)
Tmin = 0.947, Tmax = 0.957Rint = 0.069
8504 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0580 restraints
wR(F2) = 0.154H atoms treated by a mixture of independent and constrained refinement
S = 0.95Δρmax = 0.43 e Å3
3575 reflectionsΔρmin = 0.43 e Å3
240 parameters
Special details top

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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
O10.60294 (10)0.5516 (2)0.07795 (8)0.0320 (3)
O20.45903 (14)0.8527 (2)0.04912 (12)0.0550 (5)
O30.29116 (13)0.7894 (3)0.04515 (12)0.0615 (6)
O40.18616 (10)0.2220 (2)0.15681 (8)0.0312 (4)
O50.30662 (12)0.0030 (2)0.21338 (10)0.0438 (4)
O60.67789 (12)0.0254 (2)0.20283 (10)0.0431 (4)
O70.73586 (11)0.2486 (2)0.14037 (10)0.0408 (4)
N30.66203 (12)0.1781 (2)0.16407 (9)0.0223 (3)
N20.28268 (12)0.1539 (2)0.17746 (8)0.0227 (3)
N10.38972 (12)0.7422 (2)0.06093 (9)0.0243 (3)
N40.81992 (11)0.61547 (19)0.09625 (7)0.0149 (3)
N50.97556 (10)0.7577 (2)0.19366 (7)0.0157 (3)
N61.00739 (11)0.59303 (19)0.08449 (8)0.0160 (3)
N70.91067 (11)0.91728 (19)0.07003 (8)0.0151 (3)
C10.53481 (13)0.4662 (2)0.10504 (9)0.0182 (3)
C20.42297 (13)0.5466 (2)0.09739 (9)0.0171 (3)
C30.34367 (13)0.4483 (2)0.12158 (9)0.0168 (3)
H3A0.27330.50540.11430.020*
C40.36892 (13)0.2631 (2)0.15695 (9)0.0170 (3)
C50.47419 (13)0.1785 (2)0.17098 (9)0.0175 (3)
H5A0.49080.05670.19660.021*
C60.55404 (13)0.2770 (2)0.14654 (9)0.0176 (3)
C70.86933 (13)0.6544 (2)0.17982 (9)0.0167 (3)
H7A0.81810.73610.19780.020*
H7B0.88020.52740.20680.020*
C80.90167 (14)0.4883 (2)0.06953 (9)0.0174 (3)
H8A0.91270.35970.09540.021*
H8B0.87170.46290.01610.021*
C90.80422 (13)0.8160 (2)0.05523 (9)0.0162 (3)
H9A0.77300.79380.00170.019*
H9B0.75240.89940.07200.019*
C101.05185 (13)0.6316 (2)0.16567 (9)0.0181 (3)
H10A1.12370.69860.17580.022*
H10B1.06350.50420.19240.022*
C110.98830 (13)0.7876 (2)0.04477 (9)0.0173 (3)
H11A0.95800.76350.00870.021*
H11B1.05930.85680.05320.021*
C120.95718 (13)0.9492 (2)0.15161 (9)0.0169 (3)
H12A0.90621.03260.16910.020*
H12B1.02771.02070.16150.020*
H1N40.751 (2)0.550 (3)0.0879 (14)0.046 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0130 (6)0.0422 (8)0.0414 (8)0.0030 (5)0.0087 (6)0.0185 (6)
O20.0472 (10)0.0246 (8)0.1038 (16)0.0003 (7)0.0387 (10)0.0197 (8)
O30.0211 (8)0.0479 (10)0.1066 (16)0.0081 (7)0.0046 (9)0.0446 (10)
O40.0117 (6)0.0399 (8)0.0434 (8)0.0009 (5)0.0104 (6)0.0099 (6)
O50.0277 (8)0.0465 (9)0.0591 (10)0.0008 (6)0.0156 (7)0.0337 (8)
O60.0261 (8)0.0465 (9)0.0603 (11)0.0174 (6)0.0181 (7)0.0281 (8)
O70.0222 (7)0.0264 (7)0.0838 (13)0.0037 (5)0.0310 (8)0.0089 (7)
N30.0146 (7)0.0219 (7)0.0309 (8)0.0009 (5)0.0074 (6)0.0016 (6)
N20.0145 (7)0.0314 (8)0.0226 (7)0.0016 (6)0.0062 (6)0.0078 (6)
N10.0219 (8)0.0202 (7)0.0281 (8)0.0014 (6)0.0032 (6)0.0033 (6)
N40.0103 (6)0.0165 (6)0.0183 (7)0.0016 (5)0.0048 (5)0.0009 (5)
N50.0119 (6)0.0188 (6)0.0160 (6)0.0006 (5)0.0033 (5)0.0012 (5)
N60.0148 (7)0.0172 (6)0.0183 (7)0.0019 (5)0.0082 (5)0.0020 (5)
N70.0143 (6)0.0144 (6)0.0175 (6)0.0007 (5)0.0058 (5)0.0019 (5)
C10.0115 (7)0.0242 (8)0.0181 (8)0.0041 (6)0.0030 (6)0.0002 (6)
C20.0139 (8)0.0174 (7)0.0184 (8)0.0014 (6)0.0022 (6)0.0011 (6)
C30.0117 (7)0.0219 (8)0.0165 (7)0.0001 (6)0.0035 (6)0.0013 (6)
C40.0116 (8)0.0229 (8)0.0176 (8)0.0023 (6)0.0062 (6)0.0021 (6)
C50.0143 (8)0.0190 (7)0.0181 (8)0.0000 (6)0.0031 (6)0.0012 (6)
C60.0099 (7)0.0218 (8)0.0204 (8)0.0006 (6)0.0033 (6)0.0016 (6)
C70.0158 (8)0.0218 (8)0.0145 (7)0.0005 (6)0.0078 (6)0.0019 (6)
C80.0188 (8)0.0142 (7)0.0208 (8)0.0001 (6)0.0083 (6)0.0020 (6)
C90.0118 (7)0.0185 (7)0.0166 (7)0.0026 (5)0.0016 (6)0.0020 (6)
C100.0124 (7)0.0223 (8)0.0189 (8)0.0044 (6)0.0034 (6)0.0039 (6)
C110.0164 (8)0.0193 (8)0.0192 (8)0.0014 (6)0.0099 (6)0.0031 (6)
C120.0159 (7)0.0141 (7)0.0204 (8)0.0018 (5)0.0049 (6)0.0023 (6)
Geometric parameters (Å, º) top
O1—C11.2456 (19)N7—C121.474 (2)
O2—N11.2037 (19)C1—C61.457 (2)
O3—N11.221 (2)C1—C21.464 (2)
O4—N21.2393 (18)C2—C31.368 (2)
O5—N21.2258 (19)C3—C41.386 (2)
O6—N31.226 (2)C3—H3A0.9300
O7—N31.2262 (18)C4—C51.383 (2)
N3—C61.449 (2)C5—C61.377 (2)
N2—C41.4403 (19)C5—H5A0.9300
N1—C21.467 (2)C7—H7A0.9700
N4—C81.517 (2)C7—H7B0.9700
N4—C91.5181 (19)C8—H8A0.9700
N4—C71.519 (2)C8—H8B0.9700
N4—H1N40.94 (3)C9—H9A0.9700
N5—C71.4488 (19)C9—H9B0.9700
N5—C101.4737 (19)C10—H10A0.9700
N5—C121.474 (2)C10—H10B0.9700
N6—C81.446 (2)C11—H11A0.9700
N6—C111.4719 (19)C11—H11B0.9700
N6—C101.472 (2)C12—H12A0.9700
N7—C91.4431 (19)C12—H12B0.9700
N7—C111.4733 (19)
O6—N3—O7121.20 (15)C5—C6—N3115.37 (14)
O6—N3—C6119.06 (14)C5—C6—C1124.14 (14)
O7—N3—C6119.74 (14)N3—C6—C1120.49 (14)
O5—N2—O4122.60 (14)N5—C7—N4109.83 (12)
O5—N2—C4119.32 (14)N5—C7—H7A109.7
O4—N2—C4118.07 (14)N4—C7—H7A109.7
O2—N1—O3121.94 (16)N5—C7—H7B109.7
O2—N1—C2120.14 (15)N4—C7—H7B109.7
O3—N1—C2117.89 (14)H7A—C7—H7B108.2
C8—N4—C9108.82 (12)N6—C8—N4109.58 (12)
C8—N4—C7108.64 (12)N6—C8—H8A109.8
C9—N4—C7108.69 (12)N4—C8—H8A109.8
C8—N4—H1N4111.3 (14)N6—C8—H8B109.8
C9—N4—H1N4110.2 (15)N4—C8—H8B109.8
C7—N4—H1N4109.2 (15)H8A—C8—H8B108.2
C7—N5—C10108.83 (12)N7—C9—N4109.62 (12)
C7—N5—C12108.73 (12)N7—C9—H9A109.7
C10—N5—C12108.51 (12)N4—C9—H9A109.7
C8—N6—C11108.66 (12)N7—C9—H9B109.7
C8—N6—C10109.30 (12)N4—C9—H9B109.7
C11—N6—C10108.68 (12)H9A—C9—H9B108.2
C9—N7—C11108.89 (12)N6—C10—N5111.90 (12)
C9—N7—C12109.09 (12)N6—C10—H10A109.2
C11—N7—C12108.35 (12)N5—C10—H10A109.2
O1—C1—C6125.47 (15)N6—C10—H10B109.2
O1—C1—C2122.79 (15)N5—C10—H10B109.2
C6—C1—C2111.73 (13)H10A—C10—H10B107.9
C3—C2—C1123.88 (15)N6—C11—N7112.14 (12)
C3—C2—N1116.08 (14)N6—C11—H11A109.2
C1—C2—N1120.03 (14)N7—C11—H11A109.2
C2—C3—C4119.52 (15)N6—C11—H11B109.2
C2—C3—H3A120.2N7—C11—H11B109.2
C4—C3—H3A120.2H11A—C11—H11B107.9
C5—C4—C3121.41 (14)N7—C12—N5112.13 (12)
C5—C4—N2119.35 (14)N7—C12—H12A109.2
C3—C4—N2119.21 (14)N5—C12—H12A109.2
C6—C5—C4119.11 (15)N7—C12—H12B109.2
C6—C5—H5A120.4N5—C12—H12B109.2
C4—C5—H5A120.4H12A—C12—H12B107.9
O1—C1—C2—C3174.80 (16)O1—C1—C6—N34.4 (3)
C6—C1—C2—C34.4 (2)C2—C1—C6—N3176.45 (14)
O1—C1—C2—N14.2 (3)C10—N5—C7—N459.11 (16)
C6—C1—C2—N1176.62 (14)C12—N5—C7—N458.91 (15)
O2—N1—C2—C3167.90 (18)C8—N4—C7—N559.14 (15)
O3—N1—C2—C310.3 (2)C9—N4—C7—N559.12 (15)
O2—N1—C2—C113.0 (3)C11—N6—C8—N459.31 (16)
O3—N1—C2—C1168.81 (18)C10—N6—C8—N459.14 (16)
C1—C2—C3—C41.3 (3)C9—N4—C8—N659.25 (16)
N1—C2—C3—C4179.67 (14)C7—N4—C8—N658.93 (15)
C2—C3—C4—C52.5 (2)C11—N7—C9—N458.91 (16)
C2—C3—C4—N2175.61 (15)C12—N7—C9—N459.16 (15)
O5—N2—C4—C56.9 (2)C8—N4—C9—N759.03 (16)
O4—N2—C4—C5172.03 (15)C7—N4—C9—N759.12 (15)
O5—N2—C4—C3174.93 (17)C8—N6—C10—N560.44 (16)
O4—N2—C4—C36.1 (2)C11—N6—C10—N557.99 (16)
C3—C4—C5—C62.6 (3)C7—N5—C10—N660.22 (16)
N2—C4—C5—C6175.49 (14)C12—N5—C10—N657.94 (16)
C4—C5—C6—N3179.64 (14)C8—N6—C11—N760.76 (16)
C4—C5—C6—C11.0 (3)C10—N6—C11—N758.08 (16)
O6—N3—C6—C54.9 (2)C9—N7—C11—N660.66 (17)
O7—N3—C6—C5175.43 (17)C12—N7—C11—N657.88 (16)
O6—N3—C6—C1175.74 (16)C9—N7—C12—N560.49 (16)
O7—N3—C6—C13.9 (3)C11—N7—C12—N557.92 (16)
O1—C1—C6—C5174.91 (17)C7—N5—C12—N760.16 (16)
C2—C1—C6—C54.3 (2)C10—N5—C12—N758.06 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H14N···O10.94 (2)1.81 (3)2.666 (2)152 (2)
N4—H14N···O70.94 (2)2.26 (2)2.865 (2)122 (2)
C12—H12A···O7i0.972.493.362 (2)149
C12—H12B···O4ii0.972.413.364 (2)167
C5—H5A···Cgiii0.933.304.07142
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z; (iii) x+1, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC6H13N4+·C6H2N3O7
Mr369.31
Crystal system, space groupMonoclinic, P21/c
Temperature (K)183
a, b, c (Å)12.4995 (2), 6.6344 (1), 18.6203 (2)
β (°) 107.022 (1)
V3)1476.48 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.14
Crystal size (mm)0.40 × 0.40 × 0.32
Data collection
DiffractometerSiemens SMART CCD area detector
diffractometer
Absorption correctionEmpirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.947, 0.957
No. of measured, independent and
observed [I > 2σ(I)] reflections
8504, 3575, 2697
Rint0.069
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.154, 0.95
No. of reflections3575
No. of parameters240
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.43, 0.43

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Selected geometric parameters (Å, º) top
O1—C11.2456 (19)N5—C71.4488 (19)
O2—N11.2037 (19)N5—C101.4737 (19)
O3—N11.221 (2)N5—C121.474 (2)
O4—N21.2393 (18)N6—C81.446 (2)
O5—N21.2258 (19)N6—C111.4719 (19)
O6—N31.226 (2)N6—C101.472 (2)
O7—N31.2262 (18)N7—C91.4431 (19)
N4—C81.517 (2)N7—C111.4733 (19)
N4—C91.5181 (19)N7—C121.474 (2)
N4—C71.519 (2)
O6—N3—O7121.20 (15)O2—N1—O3121.94 (16)
O5—N2—O4122.60 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H14N···O10.94 (2)1.81 (3)2.666 (2)152 (2)
N4—H14N···O70.94 (2)2.26 (2)2.865 (2)122 (2)
C12—H12A···O7i0.972.493.362 (2)149
C12—H12B···O4ii0.972.413.364 (2)167
C5—H5A···Cgiii0.933.304.07142
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z; (iii) x+1, y1/2, z+1/2.
Puckering parameters of the six-membered N-C-N-C-N-C ring of the HMT+ cation. top
RingQ2(Å)Q3(Å)QT(Å)θ(°)
A0.010 (2)-0.598 (2)0.598 (2)179.0 (2)
B0.011 (2)0.598 (2)0.598 (2)1.0 (2)
C0.009 (2)-0.599 (2)0.599 (2)179.0 (2)
D0.001 (2)0.577 (2)0.577 (2)0.0 (2)
The A, B, C, D rings are defined by N4-C7-N5-C10-N6-C8, N4-C7-N5-C12-N7-C9, N4-C8-N6-C11-N7-C9, and N5-C10-N6-C11-N7-C12, respectively.
 

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