5-Amino-1-methyl-4H-tetra­zolium picrate

The title compound, C₂H₆N₅⁺·C₆H₂N₃O₇^-, was prepared by the equimolar reaction of 5-amino-1-methyl­tetra­zole with picric acid. In the salt, the N⁴ atom of the tetra­zole ring is protonated. Cations and anions in (I) are linked together by a complex set of hydrogen bonds, forming polymeric chains extending along the a axis, with van der Waals inter­actions between the chains.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.044
• wR factor = 0.133
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N14
PLAT432_ALERT_2_C Short Inter X...Y Contact  O7     ..  C6      ..       2.93 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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

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Computing details

Data collection: R3m Software (Nicolet, 1980); cell refinement: R3m Software; data reduction: R3m Software; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

5-Amino-1-methyl-4H-tetrazolium picrate

Crystal data

C2H6N5^+·C6H2N3O7^−	Z = 2
Mr = 328.22	F(000) = 336
Triclinic, P1	Dx = 1.691 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9278 (11) Å	Cell parameters from 25 reflections
b = 10.234 (2) Å	θ = 16.4–22.0°
c = 11.6013 (18) Å	µ = 0.15 mm^−1
α = 107.311 (14)°	T = 292 K
β = 100.662 (14)°	Prism, yellow
γ = 98.548 (15)°	0.42 × 0.40 × 0.24 mm
V = 644.6 (2) Å^3

Data collection

Nicolet R3m four-circle diffractometer	Rint = 0.009
Radiation source: fine-focus sealed tube	θmax = 30.1°, θmin = 1.9°
Graphite monochromator	h = 0→8
ω/2θ scans	k = −14→14
4267 measured reflections	l = −16→16
3796 independent reflections	3 standard reflections every 100 reflections
3152 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.075P)^2 + 0.1158P] where P = (Fo^2 + 2Fc^2)/3
3796 reflections	(Δ/σ)max = 0.001
227 parameters	Δρmax = 0.27 e Å^−3
3 restraints	Δρmin = −0.28 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.34719 (17)	0.85997 (10)	0.78897 (9)	0.0355 (2)
N2	0.5109 (2)	0.98214 (12)	0.82422 (11)	0.0475 (3)
N3	0.6512 (2)	0.96517 (13)	0.75340 (12)	0.0520 (3)
N4	0.58207 (19)	0.83245 (12)	0.67184 (10)	0.0425 (2)
H4	0.655 (4)	0.795 (2)	0.6101 (19)	0.071 (6)*
C5	0.39139 (19)	0.76622 (12)	0.69277 (10)	0.0338 (2)
C6	0.1617 (2)	0.84457 (15)	0.85306 (13)	0.0469 (3)
H6A	0.0275	0.8723	0.8149	0.070*
H6B	0.2169	0.9028	0.9389	0.070*
H6C	0.1182	0.7484	0.8478	0.070*
N7	0.2718 (2)	0.63716 (12)	0.63062 (11)	0.0472 (3)
H7A	0.329 (3)	0.5867 (17)	0.5759 (13)	0.057*
H7B	0.154 (2)	0.6037 (19)	0.6542 (16)	0.057*
C8	0.3783 (2)	0.32486 (11)	0.63456 (10)	0.0335 (2)
C9	0.5613 (2)	0.38219 (11)	0.74857 (10)	0.0355 (2)
C10	0.5415 (2)	0.36023 (12)	0.85830 (10)	0.0364 (2)
H10	0.668 (3)	0.3957 (17)	0.9299 (15)	0.046 (4)*
C11	0.3360 (2)	0.27969 (11)	0.86185 (10)	0.0357 (2)
C12	0.1508 (2)	0.21726 (12)	0.75710 (11)	0.0361 (2)
H12	0.007 (3)	0.1659 (18)	0.7606 (15)	0.049 (4)*
C13	0.1760 (2)	0.23760 (11)	0.64826 (10)	0.0336 (2)
N14	0.7830 (2)	0.46843 (11)	0.75269 (11)	0.0444 (2)
N15	−0.02163 (19)	0.16891 (11)	0.54043 (10)	0.0399 (2)
N16	0.3134 (2)	0.25927 (11)	0.97752 (10)	0.0441 (3)
O1	0.38597 (18)	0.34910 (9)	0.53556 (8)	0.0439 (2)
O2	0.8017 (3)	0.50964 (16)	0.66558 (12)	0.0821 (5)
O3	0.9449 (2)	0.49832 (15)	0.84373 (13)	0.0697 (4)
O4	0.01818 (19)	0.12325 (11)	0.43718 (8)	0.0506 (2)
O5	−0.21971 (18)	0.15707 (14)	0.55753 (11)	0.0618 (3)
O6	0.4698 (2)	0.32263 (12)	1.07161 (9)	0.0582 (3)
O7	0.1383 (3)	0.17898 (14)	0.97687 (11)	0.0709 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0361 (5)	0.0351 (5)	0.0332 (4)	0.0051 (4)	0.0101 (4)	0.0088 (3)
N2	0.0472 (6)	0.0385 (5)	0.0470 (6)	−0.0020 (4)	0.0101 (5)	0.0062 (4)
N3	0.0456 (6)	0.0517 (6)	0.0498 (6)	−0.0071 (5)	0.0111 (5)	0.0132 (5)
N4	0.0368 (5)	0.0524 (6)	0.0352 (5)	0.0020 (4)	0.0115 (4)	0.0122 (4)
C5	0.0340 (5)	0.0384 (5)	0.0287 (4)	0.0066 (4)	0.0078 (4)	0.0112 (4)
C6	0.0426 (6)	0.0527 (7)	0.0456 (6)	0.0094 (5)	0.0208 (5)	0.0111 (5)
N7	0.0523 (6)	0.0383 (5)	0.0438 (6)	0.0024 (5)	0.0194 (5)	0.0021 (4)
C8	0.0415 (5)	0.0278 (4)	0.0322 (5)	0.0059 (4)	0.0139 (4)	0.0092 (4)
C9	0.0385 (5)	0.0300 (5)	0.0359 (5)	0.0012 (4)	0.0130 (4)	0.0087 (4)
C10	0.0422 (6)	0.0326 (5)	0.0325 (5)	0.0059 (4)	0.0099 (4)	0.0090 (4)
C11	0.0458 (6)	0.0334 (5)	0.0313 (5)	0.0083 (4)	0.0156 (4)	0.0123 (4)
C12	0.0389 (5)	0.0347 (5)	0.0373 (5)	0.0055 (4)	0.0153 (4)	0.0135 (4)
C13	0.0358 (5)	0.0321 (5)	0.0322 (5)	0.0047 (4)	0.0092 (4)	0.0102 (4)
N14	0.0445 (6)	0.0372 (5)	0.0460 (6)	−0.0030 (4)	0.0164 (5)	0.0086 (4)
N15	0.0371 (5)	0.0422 (5)	0.0400 (5)	0.0056 (4)	0.0069 (4)	0.0158 (4)
N16	0.0624 (7)	0.0407 (5)	0.0354 (5)	0.0131 (5)	0.0215 (5)	0.0148 (4)
O1	0.0585 (6)	0.0400 (4)	0.0337 (4)	0.0020 (4)	0.0154 (4)	0.0148 (3)
O2	0.0791 (9)	0.0933 (10)	0.0565 (7)	−0.0397 (7)	0.0128 (6)	0.0301 (6)
O3	0.0437 (6)	0.0831 (9)	0.0729 (8)	−0.0111 (5)	0.0012 (5)	0.0324 (7)
O4	0.0514 (5)	0.0553 (6)	0.0358 (4)	0.0029 (4)	0.0066 (4)	0.0084 (4)
O5	0.0358 (5)	0.0877 (8)	0.0604 (6)	0.0084 (5)	0.0103 (4)	0.0260 (6)
O6	0.0767 (7)	0.0636 (6)	0.0344 (4)	0.0148 (6)	0.0099 (5)	0.0191 (4)
O7	0.0864 (9)	0.0730 (8)	0.0542 (6)	−0.0092 (6)	0.0355 (6)	0.0242 (6)

Geometric parameters (Å, º)

N1—C5	1.3344 (14)	C9—C10	1.3793 (16)
N1—N2	1.3641 (15)	C9—N14	1.4541 (15)
N1—C6	1.4516 (16)	C10—C11	1.3807 (17)
N2—N3	1.2678 (18)	C10—H10	0.946 (17)
N3—N4	1.3543 (17)	C11—C12	1.3877 (17)
N4—C5	1.3295 (15)	C11—N16	1.4448 (14)
N4—H4	0.92 (2)	C12—C13	1.3700 (15)
C5—N7	1.3163 (16)	C12—H12	0.949 (19)
C6—H6A	0.9600	C13—N15	1.4562 (15)
C6—H6B	0.9600	N14—O3	1.2146 (16)
C6—H6C	0.9600	N14—O2	1.2218 (16)
N7—H7A	0.851 (8)	N15—O5	1.2210 (15)
N7—H7B	0.859 (8)	N15—O4	1.2301 (14)
C8—O1	1.2523 (13)	N16—O7	1.2219 (17)
C8—C9	1.4453 (16)	N16—O6	1.2235 (16)
C8—C13	1.4483 (16)
C5—N1—N2	109.22 (10)	C10—C9—N14	115.77 (11)
C5—N1—C6	129.06 (11)	C8—C9—N14	120.38 (10)
N2—N1—C6	121.71 (10)	C9—C10—C11	119.17 (11)
N3—N2—N1	108.05 (11)	C9—C10—H10	121.3 (10)
N2—N3—N4	108.06 (11)	C11—C10—H10	119.4 (10)
C5—N4—N3	109.88 (11)	C10—C11—C12	121.75 (10)
C5—N4—H4	125.4 (14)	C10—C11—N16	119.13 (11)
N3—N4—H4	124.7 (14)	C12—C11—N16	119.11 (11)
N7—C5—N4	127.25 (11)	C13—C12—C11	118.19 (11)
N7—C5—N1	127.96 (11)	C13—C12—H12	120.1 (10)
N4—C5—N1	104.78 (10)	C11—C12—H12	121.7 (10)
N1—C6—H6A	109.5	C12—C13—C8	125.01 (10)
N1—C6—H6B	109.5	C12—C13—N15	116.32 (10)
H6A—C6—H6B	109.5	C8—C13—N15	118.63 (9)
N1—C6—H6C	109.5	O3—N14—O2	121.71 (12)
H6A—C6—H6C	109.5	O3—N14—C9	118.72 (11)
H6B—C6—H6C	109.5	O2—N14—C9	119.57 (12)
C5—N7—H7A	117.2 (13)	O5—N15—O4	123.08 (12)
C5—N7—H7B	119.4 (13)	O5—N15—C13	118.05 (11)
H7A—N7—H7B	122.6 (19)	O4—N15—C13	118.85 (10)
O1—C8—C9	125.30 (11)	O7—N16—O6	122.86 (12)
O1—C8—C13	122.76 (11)	O7—N16—C11	118.30 (12)
C9—C8—C13	111.91 (9)	O6—N16—C11	118.85 (12)
C10—C9—C8	123.85 (10)
C5—N1—N2—N3	−0.16 (15)	N16—C11—C12—C13	−179.81 (10)
C6—N1—N2—N3	179.33 (12)	C11—C12—C13—C8	−2.84 (18)
N1—N2—N3—N4	−0.26 (15)	C11—C12—C13—N15	179.35 (10)
N2—N3—N4—C5	0.59 (16)	O1—C8—C13—C12	−174.27 (11)
N3—N4—C5—N7	178.49 (13)	C9—C8—C13—C12	3.83 (16)
N3—N4—C5—N1	−0.67 (13)	O1—C8—C13—N15	3.49 (16)
N2—N1—C5—N7	−178.64 (12)	C9—C8—C13—N15	−178.41 (10)
C6—N1—C5—N7	1.9 (2)	C10—C9—N14—O3	10.21 (18)
N2—N1—C5—N4	0.51 (13)	C8—C9—N14—O3	−169.61 (12)
C6—N1—C5—N4	−178.93 (12)	C10—C9—N14—O2	−169.33 (14)
O1—C8—C9—C10	175.89 (11)	C8—C9—N14—O2	10.86 (19)
C13—C8—C9—C10	−2.16 (16)	C12—C13—N15—O5	33.91 (16)
O1—C8—C9—N14	−4.31 (18)	C8—C13—N15—O5	−144.05 (12)
C13—C8—C9—N14	177.64 (10)	C12—C13—N15—O4	−144.71 (12)
C8—C9—C10—C11	−0.36 (18)	C8—C13—N15—O4	37.33 (15)
N14—C9—C10—C11	179.83 (10)	C10—C11—N16—O7	−174.36 (12)
C9—C10—C11—C12	1.67 (18)	C12—C11—N16—O7	5.32 (18)
C9—C10—C11—N16	−178.66 (10)	C10—C11—N16—O6	5.56 (18)
C10—C11—C12—C13	−0.14 (18)	C12—C11—N16—O6	−174.76 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O1^i	0.92 (2)	1.83 (2)	2.6249 (15)	143 (2)
N4—H4···O4^i	0.92 (2)	2.22 (2)	2.9242 (16)	132.5 (18)
N7—H7A···O1	0.85 (1)	2.42 (2)	3.0496 (16)	131 (2)
N7—H7A···O1^i	0.85 (1)	2.44 (2)	3.0621 (16)	131 (2)
N7—H7A···O2^i	0.85 (1)	2.60 (1)	3.2303 (19)	132 (2)
N7—H7B···O2^ii	0.86 (1)	2.21 (1)	3.0472 (18)	165 (2)

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