1-[6-(3,5-Di­methyl­pyrazol-1-yl)-1,2,4,5-tetra­zin-3-yl]guanidin-2-ium perchlorate methanol monosolvate

Hu, Y.-P.; Yan, B.; Li, J.; Ma, H.-X.

doi:10.1107/S1600536813020448

organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1332

doi:10.1107/S1600536813020448

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1-[6-(3,5-Dimethylpyrazol-1-yl)-1,2,4,5-tetrazin-3-yl]guanidin-2-ium perchlorate methanol monosolvate

Yong-Peng Hu,^a Biao Yan,^a,^b Jie Li ^a and Hai-Xia Ma ^a ^*

^aSchool of Chemical Engineering, Northwest University, Xi'an 710069, Shaanxi, People's Republic of China, and ^bSchool of Chemistry and Chemical Engineering, Yulin University, Yulin 719000, Shaanxi, People's Republic of China
^*Correspondence e-mail: donghuhai@qq.com

(Received 25 June 2013; accepted 23 July 2013; online 27 July 2013)

In the title solvated salt, C₈H₁₂N₉⁺·ClO₄⁻·CH₃OH, the dihedral angle between the tetrazine and pyrazole rings is 26.05 (7)°. The two N atoms bonded to the 1,2,4,5-tetrazine ring deviate from the plane defined by its four N atoms by 0.234 (2) and 0.186 (2) Å. There is an intramolecular N—H⋯N hydrogen bond between the protonated guanidine fragment and one of the tetrazine N atoms. In the crystal, two cations and two perchlorate anions are connected via N—H⋯O hydrogen bonds into centrosymmetric assemblies. These assemblies are further linked into a two-dimensional network parallel to (100) via bifurcated O—H⋯(N,N) hydrogen bonds formed with the bridging methanol molecules.

Related literature

For 1,2,4,5-tetrazine heterocycles containing strained ring systems, see: Boger & Zhang (1991 ); Chavez et al. (2004 ); Saikia et al. (2009 ).

Experimental

Crystal data

C₈H₁₂N₉⁺·ClO₄⁻·CH₄O
M_r = 365.76
Monoclinic, P 2₁ /c
a = 12.7906 (15) Å
b = 8.0149 (10) Å
c = 16.644 (2) Å
β = 108.305 (1)°
V = 1619.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 296 K
0.38 × 0.28 × 0.19 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.902, T_max = 0.948
7710 measured reflections
2875 independent reflections
2426 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.113
S = 1.06
2875 reflections
222 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ⁱ	0.86	2.54	3.101 (3)	124
O5—H5⋯N9ⁱⁱ	0.82	2.05	2.866 (2)	173
O5—H5⋯N5ⁱⁱ	0.82	2.50	2.940 (2)	114
N2—H2A⋯O3ⁱⁱⁱ	0.86	2.50	3.251 (3)	146
N2—H2A⋯O2ⁱⁱⁱ	0.86	2.37	3.118 (3)	146
N1—H1A⋯O2ⁱⁱⁱ	0.86	2.37	3.120 (3)	146
N3—H3⋯O5	0.86	1.90	2.700 (2)	153
N2—H2B⋯N7	0.86	2.09	2.713 (2)	129
N1—H1B⋯O5	0.86	2.37	3.085 (3)	140
Symmetry codes: (i) -x+1, -y+1, -z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y+1, z.

Data collection: APEX2 (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536813020448/gk2585sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813020448/gk2585Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813020448/gk2585Isup3.cml

checkCIF report

Comment top

Heterocycles with high nitrogen and low carbon content that are free of halogens possess desirable stability. Recently, considerable attention has been paid to 1,2,4,5-tetrazine heterocycles containing strained ring systems (Boger and Zhang, 1991; Chavez et al., 2004; Saikia et al., 2009). This makes them good candidates for energetic materials (propellants or explosives). Heteroatom substituted tetrazine derivatives such as 3,6-diguanidino-1,2,4,5-tetrazine (DGTz) (Chavez et al., 2004) and 3,6-bis(1H-1,2,3,4-tetrazol-5-ylamino)-1,2,4,5-tetrazine (BTATz) (Saikia et al., 2009) are readily accessible from 3,6-bis(3,5-dimethylpyrazol-1-yl)-1,2,4,5-tetrazine (BT). 3-Guanidyl-6-(3,5-dimethylpyrazol-1-yl)-1,2,4,5-tetrazine (GDPTz) also is a derivative of BT and we report here the crystal structure of its perchlorate salt methanol monosolvate..

Related literature top

For 1,2,4,5-tetrazine heterocycles containing strained ring systems, see: Boger & Zhang (1991); Chavez et al. (2004); Saikia et al. (2009).

Experimental top

Methanol (100 ml), guanidinium nitrate (11.8 g,0.098 mol) and sodium methoxide (4.4 g 0.098 mol) were stirred for 45 minutes. 3,6-Bis(3,5-dimethylpyrazol-1-yl)-1,2,4,5-tetrazine (12.4 g, 46 mmol) was added in one portion and stirred at room temperature for 12 h. The dark red slurry, composed mainly of DGTz mixed with a small amount of GDPTz, was filtered and washed with amounts of copious water and transferred to a 500 ml beaker. The solids were suspended in water (200 ml) and 70% perchloric acid (32 ml) was added with stirring; the suspension slowly turned into an orange solution. Orange needles precipitate was gained after a few minutes of stirring. The slurry was heated to re-dissolve the precipitate and cooled to room temperature and then placed in the refrigerator for several hours. The orange needles were collected by filtration, the filtrate was concentrated in vacuo, the solid product was washed with ethanol and purified by recrystallization from methanol to give the pure saffron compound in 4.1% yield. Crystals were obtained from methanol, by slow evaporation at room temperature. Elemental analysis calculated for C₉H₁₆N₉O₅Cl: C 29.56, N 34.47, H 4.41%; found: C 29.19, N 34.10, H 4.60%.

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Crystal packing diagram. Hydrogen bonds are shown with dashed lines.

1-[6-(3,5-Dimethylpyrazol-1-yl)-1,2,4,5-tetrazin-3-yl]guanidin-2-ium perchlorate methanol monosolvate top

Crystal data top

C₈H₁₂N₉⁺·ClO₄⁻·CH₄O	F(000) = 760
M_r = 365.76	D_x = 1.500 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3433 reflections
a = 12.7906 (15) Å	θ = 2.6–25.8°
b = 8.0149 (10) Å	µ = 0.28 mm⁻¹
c = 16.644 (2) Å	T = 296 K
β = 108.305 (1)°	Block, yellow
V = 1619.9 (3) Å³	0.38 × 0.28 × 0.19 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2875 independent reflections
Radiation source: fine-focus sealed tube	2426 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
phi and ω scans	θ_max = 25.1°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −14→15
T_min = 0.902, T_max = 0.948	k = −9→6
7710 measured reflections	l = −19→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.113	w = 1/[σ²(F_o²) + (0.0557P)² + 0.5826P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2875 reflections	Δρ_max = 0.24 e Å⁻³
222 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0149 (15)

Crystal data top

C₈H₁₂N₉⁺·ClO₄⁻·CH₄O	V = 1619.9 (3) Å³
M_r = 365.76	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.7906 (15) Å	µ = 0.28 mm⁻¹
b = 8.0149 (10) Å	T = 296 K
c = 16.644 (2) Å	0.38 × 0.28 × 0.19 mm
β = 108.305 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2875 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	2426 reflections with I > 2σ(I)
T_min = 0.902, T_max = 0.948	R_int = 0.022
7710 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.06	Δρ_max = 0.24 e Å⁻³
2875 reflections	Δρ_min = −0.27 e Å⁻³
222 parameters

Special details top

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	U_iso*/U_eq
Cl	0.71723 (4)	0.14781 (6)	0.07027 (3)	0.0510 (2)
N2	0.67200 (16)	0.7743 (2)	0.19606 (13)	0.0613 (5)
H2A	0.6775	0.8725	0.1769	0.074*
H2B	0.7265	0.7322	0.2353	0.074*
N3	0.56882 (13)	0.5343 (2)	0.19387 (11)	0.0463 (4)
H3	0.5025	0.4971	0.1807	0.056*
N1	0.49649 (15)	0.7504 (3)	0.10588 (13)	0.0639 (6)
H1A	0.5002	0.8483	0.0858	0.077*
H1B	0.4373	0.6923	0.0868	0.077*
N4	0.61470 (13)	0.2743 (2)	0.24859 (12)	0.0503 (4)
N5	0.68994 (14)	0.1634 (2)	0.28457 (12)	0.0524 (5)
N6	0.82827 (13)	0.3725 (2)	0.31430 (11)	0.0510 (4)
N7	0.75184 (14)	0.4852 (2)	0.27682 (11)	0.0516 (4)
N9	0.84660 (13)	−0.0495 (2)	0.37776 (10)	0.0468 (4)
C5	0.93968 (17)	−0.1338 (2)	0.40593 (13)	0.0473 (5)
C6	1.02667 (17)	−0.0472 (3)	0.39046 (14)	0.0544 (5)
H6	1.0995	−0.0824	0.4048	0.065*
C7	0.98545 (16)	0.0966 (3)	0.35103 (13)	0.0513 (5)
N8	0.87506 (13)	0.0947 (2)	0.34434 (10)	0.0445 (4)
O1	0.69859 (19)	0.3153 (2)	0.08793 (16)	0.0991 (7)
O2	0.61828 (13)	0.0547 (2)	0.05927 (12)	0.0742 (5)
O3	0.80093 (16)	0.0795 (3)	0.13929 (14)	0.1041 (7)
O4	0.74576 (18)	0.1425 (3)	−0.00434 (12)	0.0920 (7)
O5	0.36726 (13)	0.4239 (2)	0.10212 (12)	0.0690 (5)
H5	0.3085	0.4369	0.1114	0.103*
C1	0.58130 (17)	0.6897 (2)	0.16581 (13)	0.0455 (5)
C2	0.65001 (15)	0.4300 (2)	0.24091 (12)	0.0421 (4)
C3	0.79545 (15)	0.2160 (2)	0.31182 (12)	0.0425 (4)
C4	0.9443 (2)	−0.3002 (3)	0.44739 (16)	0.0669 (7)
H4A	0.8769	−0.3192	0.4598	0.100*
H4B	1.0050	−0.3024	0.4990	0.100*
H4C	0.9540	−0.3858	0.4100	0.100*
C8	1.0389 (2)	0.2301 (4)	0.3155 (2)	0.0821 (9)
H8A	1.0451	0.3296	0.3488	0.123*
H8B	0.9950	0.2528	0.2582	0.123*
H8C	1.1109	0.1941	0.3166	0.123*
C9	0.3592 (3)	0.2881 (5)	0.0482 (3)	0.1234 (15)
H9A	0.4295	0.2681	0.0405	0.185*
H9B	0.3056	0.3116	−0.0056	0.185*
H9C	0.3371	0.1910	0.0725	0.185*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0464 (3)	0.0461 (3)	0.0566 (3)	−0.0045 (2)	0.0103 (2)	0.0036 (2)
N2	0.0621 (12)	0.0374 (10)	0.0784 (13)	−0.0025 (9)	0.0135 (10)	0.0134 (9)
N3	0.0380 (8)	0.0378 (9)	0.0616 (10)	0.0032 (7)	0.0136 (8)	0.0093 (8)
N1	0.0550 (11)	0.0606 (12)	0.0739 (13)	0.0101 (9)	0.0171 (9)	0.0296 (10)
N4	0.0410 (9)	0.0407 (9)	0.0675 (11)	0.0020 (7)	0.0144 (8)	0.0137 (8)
N5	0.0423 (9)	0.0399 (9)	0.0713 (12)	0.0019 (7)	0.0127 (8)	0.0140 (8)
N6	0.0429 (9)	0.0379 (9)	0.0628 (11)	0.0010 (7)	0.0033 (8)	0.0040 (8)
N7	0.0481 (10)	0.0351 (9)	0.0636 (11)	0.0008 (7)	0.0058 (8)	0.0042 (8)
N9	0.0450 (9)	0.0371 (9)	0.0537 (10)	0.0021 (7)	0.0091 (7)	0.0080 (7)
C5	0.0508 (11)	0.0380 (11)	0.0452 (11)	0.0100 (9)	0.0039 (9)	−0.0030 (8)
C6	0.0427 (11)	0.0534 (13)	0.0634 (13)	0.0130 (10)	0.0111 (10)	−0.0024 (10)
C7	0.0421 (11)	0.0551 (13)	0.0572 (12)	0.0039 (10)	0.0166 (9)	0.0007 (10)
N8	0.0400 (9)	0.0385 (9)	0.0524 (10)	0.0041 (7)	0.0109 (7)	0.0076 (7)
O1	0.1156 (17)	0.0471 (10)	0.152 (2)	−0.0112 (11)	0.0675 (16)	−0.0110 (12)
O2	0.0597 (10)	0.0659 (11)	0.0934 (13)	−0.0216 (9)	0.0188 (9)	0.0095 (9)
O3	0.0709 (12)	0.1261 (19)	0.0903 (14)	0.0117 (13)	−0.0106 (10)	0.0277 (13)
O4	0.0944 (14)	0.1182 (18)	0.0745 (12)	−0.0142 (13)	0.0424 (11)	−0.0052 (12)
O5	0.0487 (9)	0.0724 (11)	0.0892 (12)	−0.0052 (8)	0.0265 (8)	−0.0270 (9)
C1	0.0468 (11)	0.0395 (11)	0.0528 (11)	0.0085 (9)	0.0197 (9)	0.0077 (9)
C2	0.0407 (10)	0.0365 (10)	0.0489 (11)	0.0022 (8)	0.0138 (8)	0.0040 (8)
C3	0.0408 (10)	0.0387 (10)	0.0457 (10)	0.0020 (8)	0.0104 (8)	0.0064 (8)
C4	0.0700 (15)	0.0437 (12)	0.0730 (16)	0.0112 (11)	0.0026 (12)	0.0095 (11)
C8	0.0601 (15)	0.0845 (19)	0.113 (2)	0.0046 (14)	0.0429 (15)	0.0253 (17)
C9	0.090 (2)	0.142 (3)	0.149 (3)	−0.019 (2)	0.053 (2)	−0.089 (3)

Geometric parameters (Å, º) top

Cl—O4	1.4007 (19)	N9—N8	1.381 (2)
Cl—O1	1.410 (2)	C5—C6	1.402 (3)
Cl—O3	1.4118 (19)	C5—C4	1.494 (3)
Cl—O2	1.4307 (16)	C6—C7	1.349 (3)
N2—C1	1.301 (3)	C6—H6	0.9300
N2—H2A	0.8600	C7—N8	1.381 (2)
N2—H2B	0.8600	C7—C8	1.489 (3)
N3—C1	1.357 (3)	N8—C3	1.388 (2)
N3—C2	1.371 (2)	O5—C9	1.394 (3)
N3—H3	0.8600	O5—H5	0.8200
N1—C1	1.315 (3)	C4—H4A	0.9600
N1—H1A	0.8600	C4—H4B	0.9600
N1—H1B	0.8600	C4—H4C	0.9600
N4—N5	1.309 (2)	C8—H8A	0.9600
N4—C2	1.346 (3)	C8—H8B	0.9600
N5—C3	1.349 (3)	C8—H8C	0.9600
N6—C3	1.320 (3)	C9—H9A	0.9600
N6—N7	1.333 (2)	C9—H9B	0.9600
N7—C2	1.327 (2)	C9—H9C	0.9600
N9—C5	1.320 (2)

O4—Cl—O1	108.79 (14)	N9—N8—C3	119.30 (15)
O4—Cl—O3	111.56 (14)	C7—N8—C3	129.05 (17)
O1—Cl—O3	109.53 (16)	C9—O5—H5	109.5
O4—Cl—O2	109.68 (12)	N2—C1—N1	121.56 (19)
O1—Cl—O2	108.81 (12)	N2—C1—N3	122.16 (19)
O3—Cl—O2	108.42 (13)	N1—C1—N3	116.28 (19)
C1—N2—H2A	120.0	N7—C2—N4	125.26 (17)
C1—N2—H2B	120.0	N7—C2—N3	120.94 (17)
H2A—N2—H2B	120.0	N4—C2—N3	113.76 (16)
C1—N3—C2	127.33 (17)	N6—C3—N5	125.62 (18)
C1—N3—H3	116.3	N6—C3—N8	117.78 (17)
C2—N3—H3	116.3	N5—C3—N8	116.49 (17)
C1—N1—H1A	120.0	C5—C4—H4A	109.5
C1—N1—H1B	120.0	C5—C4—H4B	109.5
H1A—N1—H1B	120.0	H4A—C4—H4B	109.5
N5—N4—C2	116.91 (16)	C5—C4—H4C	109.5
N4—N5—C3	117.09 (16)	H4A—C4—H4C	109.5
C3—N6—N7	116.75 (16)	H4B—C4—H4C	109.5
C2—N7—N6	117.18 (16)	C7—C8—H8A	109.5
C5—N9—N8	104.42 (16)	C7—C8—H8B	109.5
N9—C5—C6	111.15 (18)	H8A—C8—H8B	109.5
N9—C5—C4	121.4 (2)	C7—C8—H8C	109.5
C6—C5—C4	127.4 (2)	H8A—C8—H8C	109.5
C7—C6—C5	107.51 (18)	H8B—C8—H8C	109.5
C7—C6—H6	126.2	O5—C9—H9A	109.5
C5—C6—H6	126.2	O5—C9—H9B	109.5
C6—C7—N8	105.28 (19)	H9A—C9—H9B	109.5
C6—C7—C8	130.5 (2)	O5—C9—H9C	109.5
N8—C7—C8	124.1 (2)	H9A—C9—H9C	109.5
N9—N8—C7	111.63 (16)	H9B—C9—H9C	109.5

C2—N4—N5—C3	1.1 (3)	C2—N3—C1—N1	164.5 (2)
C3—N6—N7—C2	0.3 (3)	N6—N7—C2—N4	9.1 (3)
N8—N9—C5—C6	−0.6 (2)	N6—N7—C2—N3	−173.48 (18)
N8—N9—C5—C4	−179.98 (19)	N5—N4—C2—N7	−9.8 (3)
N9—C5—C6—C7	0.0 (3)	N5—N4—C2—N3	172.61 (18)
C4—C5—C6—C7	179.3 (2)	C1—N3—C2—N7	11.8 (3)
C5—C6—C7—N8	0.6 (2)	C1—N3—C2—N4	−170.56 (19)
C5—C6—C7—C8	−175.8 (3)	N7—N6—C3—N5	−9.0 (3)
C5—N9—N8—C7	1.0 (2)	N7—N6—C3—N8	174.88 (17)
C5—N9—N8—C3	−177.43 (17)	N4—N5—C3—N6	8.3 (3)
C6—C7—N8—N9	−1.0 (2)	N4—N5—C3—N8	−175.54 (17)
C8—C7—N8—N9	175.7 (2)	N9—N8—C3—N6	151.36 (18)
C6—C7—N8—C3	177.2 (2)	C7—N8—C3—N6	−26.8 (3)
C8—C7—N8—C3	−6.0 (4)	N9—N8—C3—N5	−25.1 (3)
C2—N3—C1—N2	−15.4 (3)	C7—N8—C3—N5	156.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.86	2.54	3.101 (3)	124
O5—H5···N9ⁱⁱ	0.82	2.05	2.866 (2)	173
O5—H5···N5ⁱⁱ	0.82	2.50	2.940 (2)	114
N2—H2A···O3ⁱⁱⁱ	0.86	2.50	3.251 (3)	146
N2—H2A···O2ⁱⁱⁱ	0.86	2.37	3.118 (3)	146
N1—H1A···O2ⁱⁱⁱ	0.86	2.37	3.120 (3)	146
N3—H3···O5	0.86	1.90	2.700 (2)	153
N2—H2B···N7	0.86	2.09	2.713 (2)	129
N1—H1B···O5	0.86	2.37	3.085 (3)	140

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, y+1/2, −z+1/2; (iii) x, y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.86	2.54	3.101 (3)	124
O5—H5···N9ⁱⁱ	0.82	2.05	2.866 (2)	173
O5—H5···N5ⁱⁱ	0.82	2.50	2.940 (2)	114
N2—H2A···O3ⁱⁱⁱ	0.86	2.50	3.251 (3)	146
N2—H2A···O2ⁱⁱⁱ	0.86	2.37	3.118 (3)	146
N1—H1A···O2ⁱⁱⁱ	0.86	2.37	3.120 (3)	146
N3—H3···O5	0.86	1.90	2.700 (2)	153
N2—H2B···N7	0.86	2.09	2.713 (2)	129
N1—H1B···O5	0.86	2.37	3.085 (3)	140

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, y+1/2, −z+1/2; (iii) x, y+1, z.

Acknowledgements

We thank the Program for New Century Excellent Talents in Universities (No. NCET-12–1047), the National Natural Science Foundation of China (No. 21073141) and the Education Committee Foundation of Shaanxi Province (Nos. 11 J K0564 and 11 J K0582) for generously supporting this study.

References

Boger, D. L. & Zhang, M. J. (1991). J. Am. Chem. Soc. 113, 4230–4234. CrossRef CAS Web of Science Google Scholar
Bruker (2003). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chavez, D. E., Hiskey, M. A. & Naud, D. L. (2004). Propell. Explos. Pyrotech. 29, 209–215. Web of Science CrossRef CAS Google Scholar
Saikia, A., Sivabalan, R., Polke, B. G., Gore, G. M., Singh, A., Subhananda Rao, A. & Sikder, A. K. (2009). J. Hazard. Mater. 170, 306–313. Web of Science CrossRef PubMed CAS Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-[6-(3,5-Di­methyl­pyrazol-1-yl)-1,2,4,5-tetra­zin-3-yl]guanidin-2-ium perchlorate methanol monosolvate

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Experimental

Crystal data

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organic compounds

1-[6-(3,5-Dimethylpyrazol-1-yl)-1,2,4,5-tetrazin-3-yl]guanidin-2-ium perchlorate methanol monosolvate