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The structures of 2-amino-5-methyl-1,3,4-thia­diazo­le, C3H5N3S, and 2-amino-5-ethyl-1,3,4-thia­diazo­le, C4H7N3S, have been determined for comparison with unsubstituted 2-amino-1,3,4-thia­diazo­le. Despite their different space groups (P21/n and Pbca, respectively), the packing modes of the methyl and ethyl derivatives are similar, with comparable three-dimensional hydrogen-bonding associations. This is in contrast to the hydrogen-bonding network in 2-amino-1,3,4-thia­diazo­le, which is one-dimensional and has denser packing. It is shown that both packing forms are different polymorphs of a specific subunit of each array.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101011817/gg1069sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101011817/gg1069Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101011817/gg1069IIsup3.hkl
Contains datablock II

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108270101011817/gg1069sup4.pdf
Supplementary material

CCDC references: 174839; 174840

Comment top

In terms of hydrogen-bonding potential, 2-amino-1,3,4-thiadiazole has two donor elements, the 2-amino H atoms, and two acceptors, N3 and N4 in the thiadiazole ring. The structure of this compound is known (Khusenov et al., 1997) and shows a hydrogen-bonding network comprising two associated molecules linked via N—H···N interactions, graph set R22(8), which in turn associate with another molecular pair via N—H···N hydrogen bonds, graph set R44(10). The overall pattern produces a flat ribbon array (see deposited Fig.). In this network, the 5-position does not appear to affect the overall lattice packing, so the author postulated as to whether or not substitution at this point influenced the parent hydrogen-bonding network. The structures of several 5-substituted analogues are known, yet of the small substituents, such as NH2 (Senda & Maruha, 1987), SH (Downie et al., 1972) and SO2NH2 (Pedregosa et al., 1993), each is itself involved in hydrogen-bonding interactions, thus significantly altering the resultant arrays. Similarly, in the structures of the HBr (Antolini et al., 1993) and HCl.hydrate salts of 2-amino-5-methyl-1,3,4-thiadiazole (Pilz et al., 1998), the halides are involved in the hydrogen-bonding network. Larger substituents, such as those containing phenyl rings (Foresti et al., 1985; Molina et al., 1988; Leung et al., 1992; Anders et al., 1999), affect the molecular packing by their very size. Thus, the structures of 2-amino-1,3,4-thiadiazoles with simple non-hydrogen-bonding substituents, namely, 2-amino-5-methyl-1,3,4-thiadiazole, (I), and 2-amino-5-ethyl-1,3,4-thiadiazole, (II), have been investigated to elucidate the influence of these substituents on the molecular packing observed in the parent thiadiazole. \sch

Interestingly, crystals of (I) (Fig. 1) and (II) (Fig. 2) could not be obtained from simple organic solvent solutions, yet crystals of both compounds abounded when attempts were made to form adducts of these materials with aromatic carboxylic acids, such as those used by Lynch et al. (1998, 1999). For (I) and (II), the specific crystals used for data collection were separated as unreacted starting materials following the attempted formation of co-crystals of (I) with 2-aminobenzoic acid, and of (II) with N-methylpyrrole-2-carboxylic acid. The only successfully characterized co-crystal of either (I) or (II) was that of (II) with indole-2-carboxylic acid (see deposited Fig.), yet the inherent disorder in this structure, even in data collected at 150 K, yields an R value of 0.11 (Lynch et al., 1998, 1999). As expected for these types of complexes, the carboxylate groups associate across the N3/N21 sites, thus creating R22(8) graph-set dimers.

An overview of the data for (I) and (II) shows that they crystallize in monoclinic and orthorhombic space groups, respectively, yet the resultant molecular packing is quite similar. Figs. 3 and 4 display the packing for both molecules, while hydrogen-bonding geometries are listed in Tables 1 and 2, respectively. Short contact distances not listed in the tables, yet worthy of note, are for (I), S1···S1(2 - x, -y, 1 - z) 3.628 (2) Å, and for (II), S1···N4(1/2 - x, y - 1/2, z) 3.517 (2) Å.

Figs. 3 and 4 show an interesting three-dimensional hydrogen-bonded polymeric network that essentially consists of repeating ring systems made up of six associated molecules [graph set R66(20)]. As expected, both (I) and (II) form dimers via the N21—H···N3 interaction, but the main difference in packing between these two and the parent 2-amino-1,3,4-thiadiazole arises via the N21—H···N4 interaction. In 2-amino-1,3,4-thiadiazole, the dimers formed by the N21—H···N3 interaction form further dimers (via the N21—H···N4 interaction) with similarly associated molecules. In (I) and (II), the N21—H···N4 interactions from one molecular pair then link different sets of dimers. These hydrogen-bonding networks [i.e. those of (I) and (II) versus that of the parent] are essentially two different arrangements of the same dimer association, but the packing in the parent (see deposited Fig) is more dense (ρ 1.609 Mg m-3) than that shown in Figs. 3 and 4 (ρ 1.416 and 1.418 Mg m-3, respectively). It would now be interesting to elucidate the structures of both 5-propyl and 5-halo substituted 2-amino-1,3,4-thiadiazoles to determine what effect, if any, they have on the overall hydrogen-bonding networks and to determine if other packing forms are possible.

Experimental top

Crystals of (I) and (II) were separated as unreacted starting materials following the total evaporation of ethanol solutions containing equimolar amounts (2 mmol) of (I) with 2-aminobenzoic acid, and of (II) with N-methylpyrrole-2-carboxylic acid.

Refinement top

The 5-methyl and 5-ethyl H atoms were included in the refinement at calculated positions, and refined as riding models with C—H = 0.98 (CH3) or 0.99 Å (CH2). The 2-amino H atoms were located from difference syntheses and refined freely. Two packing diagrams, of the parent 2-amino-1,3,4-thiadiazole and of the co-crystal of (II) with indole-2-carboxylic acid, are available as deposited data.

Computing details top

For both compounds, data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTON94 (Spek, 1994) and PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
Fig. 1. The molecular configuration and atomic numbering scheme for (I), showing 50% probability displacement ellipsoids. H atoms are drawn as small spheres of arbitrary radii.

Fig. 2. The molecular configuration and atomic numbering scheme for (II), showing 50% probability displacement ellipsoids. H atoms are drawn as small spheres of arbitrary radii.

Fig. 3. The molecular packing for (I). Hydrogen bonds are indicated by dotted lines [symmetry codes: (i) 1 - x, 1 - y, 1 - z; (ii) 1/2 + x, 1/2 - y, 1/2 + z].

Fig. 4. The molecular packing for (II). Hydrogen bonds are indicated by dotted lines [symmetry codes: (i) 1 - x, -y, -z; (ii) 1/2 - x, 1/2 + y, z].

# Deposition Figures # Fig. 5. Molecular packing of 2-amino-1,3,4-thiadiazole. H-bonding # associations are indicated by dotted lines.

# Fig. 6. Molecular packing for the 1:1 organic salt of (II) with # indole-2-carboxylic acid. H-bonding associations are indicated by dotted # lines.
(I) 2-amino-5-methyl-1,3,4-thiadiazole top
Crystal data top
C3H5N3SDx = 1.416 Mg m3
Mr = 115.16Melting point: 497-499 K K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.5116 (17) ÅCell parameters from 9981 reflections
b = 6.5690 (13) Åθ = 2.9–30.5°
c = 10.243 (2) ŵ = 0.47 mm1
β = 109.36 (3)°T = 150 K
V = 540.34 (18) Å3Block, colourless
Z = 40.25 × 0.15 × 0.10 mm
F(000) = 240
Data collection top
Nonius KappaCCD area-detector
diffractometer
1235 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode982 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.8°
ϕ and ω scansh = 1111
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
k = 78
Tmin = 0.893, Tmax = 0.955l = 1312
7274 measured reflections
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 0.82 w = 1/[σ2(Fo2) + (0.0755P)2 + 0.3034P]
where P = (Fo2 + 2Fc2)/3
1235 reflections(Δ/σ)max < 0.001
73 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
C3H5N3SV = 540.34 (18) Å3
Mr = 115.16Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.5116 (17) ŵ = 0.47 mm1
b = 6.5690 (13) ÅT = 150 K
c = 10.243 (2) Å0.25 × 0.15 × 0.10 mm
β = 109.36 (3)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
1235 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
982 reflections with I > 2σ(I)
Tmin = 0.893, Tmax = 0.955Rint = 0.055
7274 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 0.82Δρmax = 0.25 e Å3
1235 reflectionsΔρmin = 0.26 e Å3
73 parameters
Special details top

Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

Geometry. Mean plane data ex SHELXL97 for molecule (I) ############################################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

5.6810 (0.0046) x + 3.1622 (0.0051) y - 7.7562 (0.0067) z = 0.6583 (0.0039)

* 0.0001 (0.0007) S1 * -0.0023 (0.0010) C2 * 0.0039 (0.0011) N3 * -0.0039 (0.0010) N4 * 0.0022 (0.0009) C5 0.0021 (0.0032) N21 0.0203 (0.0032) C51

Rms deviation of fitted atoms = 0.0028

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.82071 (5)0.07524 (7)0.54690 (4)0.0323 (2)
C20.6881 (2)0.2817 (3)0.53423 (17)0.0310 (4)
N210.7260 (2)0.4356 (3)0.62420 (19)0.0499 (5)
H210.662 (3)0.520 (4)0.621 (2)0.048 (7)*
H220.820 (3)0.428 (3)0.698 (2)0.041 (6)*
N30.55033 (17)0.2699 (2)0.42772 (15)0.0308 (4)
N40.54338 (17)0.0939 (2)0.35191 (15)0.0284 (3)
C50.6724 (2)0.0212 (3)0.39867 (18)0.0301 (4)
C510.6949 (3)0.2161 (3)0.3334 (2)0.0432 (5)
H510.59440.24590.25480.054*
H520.71460.32630.40140.054*
H530.79060.20480.30080.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0236 (3)0.0409 (3)0.0271 (3)0.00910 (16)0.00120 (19)0.00123 (17)
C20.0238 (8)0.0392 (10)0.0258 (9)0.0066 (7)0.0025 (7)0.0003 (7)
N210.0334 (9)0.0593 (12)0.0389 (10)0.0204 (8)0.0123 (8)0.0223 (8)
N30.0238 (7)0.0352 (8)0.0263 (7)0.0036 (6)0.0015 (6)0.0033 (6)
N40.0240 (7)0.0330 (8)0.0248 (7)0.0009 (5)0.0036 (6)0.0014 (6)
C50.0282 (8)0.0342 (9)0.0265 (9)0.0009 (7)0.0074 (7)0.0014 (7)
C510.0423 (11)0.0376 (11)0.0460 (11)0.0017 (8)0.0095 (9)0.0090 (9)
Geometric parameters (Å, º) top
S1—C21.7418 (17)N3—N41.383 (2)
S1—C51.7407 (18)N4—C51.288 (2)
C2—N31.312 (2)C5—C511.486 (3)
C2—N211.334 (2)C51—H510.98
N21—H210.77 (3)C51—H520.98
N21—H220.90 (2)C51—H530.98
C2—S1—C587.34 (8)N4—C5—C51124.04 (17)
N3—C2—N21124.35 (16)N4—C5—S1113.15 (14)
N3—C2—S1113.21 (13)C51—C5—S1122.80 (14)
N21—C2—S1122.44 (13)C5—C51—H51109.5
C2—N21—H21120.4 (18)C5—C51—H52109.5
C2—N21—H22118.9 (13)H51—C51—H52109.5
H21—N21—H22120 (2)C5—C51—H53109.5
C2—N3—N4112.12 (14)H51—C51—H53109.5
C5—N4—N3114.17 (15)H52—C51—H53109.5
C5—S1—C2—N30.26 (14)N3—N4—C5—C51178.86 (17)
C5—S1—C2—N21179.65 (19)N3—N4—C5—S10.67 (19)
N21—C2—N3—N4179.95 (18)C2—S1—C5—N40.24 (14)
S1—C2—N3—N40.66 (19)C2—S1—C5—C51179.29 (17)
C2—N3—N4—C50.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21—H21···N3i0.77 (3)2.20 (3)2.954 (2)169 (2)
N21—H22···N4ii0.90 (2)2.03 (2)2.933 (3)174 (2)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1/2, y+1/2, z+1/2.
(II) 2-amino-5-ethyl-1,3,4-thiadiazole top
Crystal data top
C4H7N3SDx = 1.418 Mg m3
Mr = 129.19Melting point: 473-476 K K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
a = 7.2752 (3) ÅCell parameters from 6797 reflections
b = 10.7294 (4) Åθ = 2.9–45.3°
c = 15.4991 (7) ŵ = 0.42 mm1
V = 1209.84 (9) Å3T = 150 K
Z = 8Block, colourless
F(000) = 5440.35 × 0.18 × 0.07 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
1385 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode1125 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.6°
ϕ and ω scansh = 98
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
k = 1213
Tmin = 0.866, Tmax = 0.971l = 1920
7813 measured reflections
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0438P)2 + 0.4846P]
where P = (Fo2 + 2Fc2)/3
1385 reflections(Δ/σ)max < 0.001
82 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
C4H7N3SV = 1209.84 (9) Å3
Mr = 129.19Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 7.2752 (3) ŵ = 0.42 mm1
b = 10.7294 (4) ÅT = 150 K
c = 15.4991 (7) Å0.35 × 0.18 × 0.07 mm
Data collection top
Nonius KappaCCD area-detector
diffractometer
1385 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
1125 reflections with I > 2σ(I)
Tmin = 0.866, Tmax = 0.971Rint = 0.041
7813 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.092H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.26 e Å3
1385 reflectionsΔρmin = 0.33 e Å3
82 parameters
Special details top

Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

Geometry. Mean plane data ex SHELXL97 for molecule (II) #############################################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

3.3710 (0.0049) x - 2.1629 (0.0058) y + 13.3748 (0.0054) z = 1.7776 (0.0009)

* -0.0042 (0.0007) S1 * 0.0048 (0.0009) C2 * -0.0031 (0.0010) N3 * -0.0014 (0.0010) N4 * 0.0039 (0.0009) C5 0.0331 (0.0027) N21 0.0545 (0.0031) C51 0.0237 (0.0035) C52

Rms deviation of fitted atoms = 0.0037

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.11939 (6)0.16283 (4)0.12883 (3)0.02593 (17)
C20.3003 (2)0.09453 (14)0.07287 (10)0.0237 (3)
N210.4472 (2)0.16103 (14)0.04870 (11)0.0327 (4)
H210.531 (3)0.126 (2)0.0179 (14)0.047 (6)*
H220.448 (3)0.240 (2)0.0578 (13)0.041 (5)*
N30.27772 (18)0.02507 (12)0.05862 (9)0.0266 (3)
N40.11361 (18)0.06880 (13)0.09304 (9)0.0265 (3)
C50.0180 (2)0.01614 (15)0.13126 (10)0.0251 (4)
C510.1606 (3)0.00415 (18)0.17678 (14)0.0378 (4)
H510.25350.05290.15200.047*
H520.14510.01820.23830.047*
C520.2327 (3)0.13618 (19)0.17130 (13)0.0382 (4)
H530.34590.14320.20520.048*
H540.14040.19390.19420.048*
H550.25840.15700.11090.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0278 (2)0.0184 (3)0.0316 (3)0.00372 (15)0.00348 (15)0.00314 (15)
C20.0255 (8)0.0198 (8)0.0260 (8)0.0035 (6)0.0003 (6)0.0003 (6)
N210.0328 (8)0.0188 (8)0.0466 (10)0.0026 (6)0.0123 (7)0.0052 (6)
N30.0258 (7)0.0187 (7)0.0354 (8)0.0007 (5)0.0065 (6)0.0030 (5)
N40.0258 (7)0.0215 (7)0.0322 (8)0.0009 (5)0.0041 (6)0.0011 (6)
C50.0260 (8)0.0208 (8)0.0287 (9)0.0014 (6)0.0002 (6)0.0012 (6)
C510.0321 (9)0.0362 (10)0.0450 (11)0.0011 (8)0.0120 (8)0.0054 (8)
C520.0327 (9)0.0446 (11)0.0372 (10)0.0108 (8)0.0074 (8)0.0028 (9)
Geometric parameters (Å, º) top
S1—C21.7380 (16)C5—C511.494 (2)
S1—C51.7385 (16)C51—C521.513 (3)
C2—N31.312 (2)C51—H510.99
C2—N211.339 (2)C51—H520.99
N21—H210.86 (2)C52—H530.98
N21—H220.85 (2)C52—H540.98
N3—N41.3893 (18)C52—H550.98
N4—C51.290 (2)
C2—S1—C587.15 (8)C5—C51—C52114.29 (15)
N3—C2—N21125.01 (15)C5—C51—H51108.7
N3—C2—S1113.68 (12)C52—C51—H51108.7
N21—C2—S1121.30 (12)C5—C51—H52108.7
C2—N21—H21118.9 (14)C52—C51—H52108.7
C2—N21—H22118.9 (14)H51—C51—H52107.6
H21—N21—H22122 (2)C51—C52—H53109.5
C2—N3—N4111.90 (13)C51—C52—H54109.5
C5—N4—N3113.63 (13)H53—C52—H54109.5
N4—C5—C51125.62 (15)C51—C52—H55109.5
N4—C5—S1113.63 (13)H53—C52—H55109.5
C51—C5—S1120.73 (13)H54—C52—H55109.5
C5—S1—C2—N30.76 (13)N3—N4—C5—S10.42 (18)
C5—S1—C2—N21178.51 (15)C2—S1—C5—N40.66 (13)
N21—C2—N3—N4178.55 (16)C2—S1—C5—C51177.61 (15)
S1—C2—N3—N40.69 (17)N4—C5—C51—C523.3 (3)
C2—N3—N4—C50.2 (2)S1—C5—C51—C52178.69 (14)
N3—N4—C5—C51177.75 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21—H21···N3i0.86 (2)2.12 (2)2.983 (2)175 (2)
N21—H22···N4ii0.85 (2)2.17 (2)3.012 (2)167 (2)
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, y+1/2, z.

Experimental details

(I)(II)
Crystal data
Chemical formulaC3H5N3SC4H7N3S
Mr115.16129.19
Crystal system, space groupMonoclinic, P21/nOrthorhombic, Pbca
Temperature (K)150150
a, b, c (Å)8.5116 (17), 6.5690 (13), 10.243 (2)7.2752 (3), 10.7294 (4), 15.4991 (7)
α, β, γ (°)90, 109.36 (3), 9090, 90, 90
V3)540.34 (18)1209.84 (9)
Z48
Radiation typeMo KαMo Kα
µ (mm1)0.470.42
Crystal size (mm)0.25 × 0.15 × 0.100.35 × 0.18 × 0.07
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Nonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1995)
Multi-scan
(SORTAV; Blessing, 1995)
Tmin, Tmax0.893, 0.9550.866, 0.971
No. of measured, independent and
observed [I > 2σ(I)] reflections
7274, 1235, 982 7813, 1385, 1125
Rint0.0550.041
(sin θ/λ)max1)0.6490.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.105, 0.82 0.036, 0.092, 1.05
No. of reflections12351385
No. of parameters7382
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.25, 0.260.26, 0.33

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLUTON94 (Spek, 1994) and PLATON97 (Spek, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N21—H21···N3i0.77 (3)2.20 (3)2.954 (2)169 (2)
N21—H22···N4ii0.90 (2)2.03 (2)2.933 (3)174 (2)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1/2, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N21—H21···N3i0.86 (2)2.12 (2)2.983 (2)175 (2)
N21—H22···N4ii0.85 (2)2.17 (2)3.012 (2)167 (2)
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, y+1/2, z.
 

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