1,2,3,5-Tetra­methyl-1H-pyrazol-2-ium triiodide

The title salt, C₇H₁₃N₂⁺·I₃⁻, was obtained unintentionally by methyl­ation of 3,6-bis­(3,5-di­methyl­pyrazol-1-yl)-1,2,4,5-tetra­zine and subsequent fragmentation. The pyrazolium ring is almost planar (r.m.s. deviation = 0.003 Å) and the triiodide anion deviates slightly from linearity [I—I—I = 177.099 (12)°]. No directional inter­actions occur in the crystal.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.026
• wR factor = 0.062
• Data-to-parameter ratio = 23.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         I2 Check

Alert level G
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....         C7 Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           2 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   0 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXTL-XT2014/4 (Sheldrick, 2015); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: Mercury (Macrae et al., 2006).

1,2,3,5-Tetramethyl-1H-pyrazol-2-ium triiodide

Crystal data

C7H13N2^+·I3^−	Dx = 2.517 Mg m^−3
Mr = 505.89	Melting point: 442 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.6719 (7) Å	Cell parameters from 9875 reflections
b = 13.4005 (9) Å	θ = 2.4–26.0°
c = 11.1874 (8) Å	µ = 6.99 mm^−1
β = 112.994 (2)°	T = 193 K
V = 1334.77 (16) Å^3	Prism, red
Z = 4	0.16 × 0.13 × 0.08 mm
F(000) = 912

Data collection

Bruker D8 QUEST PHOTON 100 diffractometer	2648 independent reflections
Radiation source: Incoatec Microfocus	2400 reflections with I > 2σ(I)
Multi layered optics monochromator	Rint = 0.028
Detector resolution: 10.4 pixels mm^-1	θmax = 26.1°, θmin = 2.4°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −16→16
Tmin = 0.397, Tmax = 0.562	l = −13→13
22167 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.026	H-atom parameters constrained
wR(F^2) = 0.062	w = 1/[σ^2(Fo^2) + (0.0207P)^2 + 3.0909P] where P = (Fo^2 + 2Fc^2)/3
S = 1.24	(Δ/σ)max = 0.001
2648 reflections	Δρmax = 0.40 e Å^−3
113 parameters	Δρmin = −1.21 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.53163 (4)	0.57210 (2)	0.18064 (3)	0.04747 (10)
I2	0.31387 (3)	0.58881 (2)	0.29850 (2)	0.02818 (8)
I3	0.09003 (3)	0.59495 (2)	0.41519 (3)	0.04406 (10)
C1	0.6156 (5)	0.8272 (3)	0.4063 (4)	0.0339 (9)
C2	0.4931 (5)	0.8817 (3)	0.4027 (4)	0.0368 (9)
H2	0.4512	0.9379	0.3490	0.044*
C3	0.4422 (4)	0.8404 (3)	0.4907 (4)	0.0337 (9)
C4	0.7113 (6)	0.8394 (4)	0.3308 (5)	0.0484 (11)
H4A	0.8144	0.8549	0.3901	0.073*
H4B	0.6719	0.8939	0.2683	0.073*
H4C	0.7107	0.7774	0.2842	0.073*
C5	0.3137 (5)	0.8684 (4)	0.5255 (5)	0.0458 (11)
H5A	0.2409	0.8136	0.5030	0.069*
H5B	0.2652	0.9285	0.4774	0.069*
H5C	0.3503	0.8816	0.6190	0.069*
C6	0.7544 (5)	0.6788 (3)	0.5368 (4)	0.0408 (10)
H6A	0.8132	0.6818	0.4827	0.061*
H6B	0.7076	0.6128	0.5282	0.061*
H6C	0.8207	0.6903	0.6278	0.061*
C7	0.5258 (5)	0.6932 (3)	0.6445 (4)	0.0361 (9)
H7A	0.4429	0.7120	0.6696	0.054*
H7B	0.6206	0.6954	0.7210	0.054*
H7C	0.5092	0.6255	0.6086	0.054*
N1	0.6383 (4)	0.7550 (2)	0.4950 (3)	0.0294 (7)
N2	0.5329 (4)	0.7627 (2)	0.5471 (3)	0.0295 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.04624 (18)	0.05257 (19)	0.0537 (2)	−0.00103 (13)	0.03051 (15)	−0.00763 (14)
I2	0.03148 (14)	0.02296 (13)	0.02863 (14)	−0.00115 (9)	0.01014 (11)	−0.00118 (9)
I3	0.04725 (18)	0.04483 (18)	0.05066 (19)	0.00210 (12)	0.03060 (15)	0.00475 (13)
C1	0.043 (2)	0.0233 (18)	0.033 (2)	−0.0066 (16)	0.0124 (17)	−0.0009 (15)
C2	0.046 (2)	0.0222 (18)	0.033 (2)	0.0001 (17)	0.0053 (18)	0.0019 (16)
C3	0.033 (2)	0.0242 (18)	0.036 (2)	0.0010 (15)	0.0043 (17)	−0.0058 (16)
C4	0.060 (3)	0.044 (3)	0.046 (3)	−0.010 (2)	0.026 (2)	0.002 (2)
C5	0.038 (2)	0.039 (2)	0.058 (3)	0.0099 (19)	0.017 (2)	−0.006 (2)
C6	0.041 (2)	0.037 (2)	0.043 (2)	0.0130 (18)	0.0160 (19)	0.0050 (19)
C7	0.046 (2)	0.030 (2)	0.032 (2)	0.0008 (17)	0.0161 (18)	0.0053 (16)
N1	0.0321 (16)	0.0241 (16)	0.0311 (16)	0.0013 (13)	0.0114 (13)	0.0003 (12)
N2	0.0341 (17)	0.0245 (15)	0.0294 (16)	0.0015 (13)	0.0117 (14)	0.0010 (13)

Geometric parameters (Å, º)

I1—I2	2.8972 (4)	C5—H5A	0.9800
I2—I3	2.9336 (4)	C5—H5B	0.9800
C1—N1	1.340 (5)	C5—H5C	0.9800
C1—C2	1.379 (6)	C6—N1	1.454 (5)
C1—C4	1.486 (6)	C6—H6A	0.9800
C2—C3	1.377 (6)	C6—H6B	0.9800
C2—H2	0.9500	C6—H6C	0.9800
C3—N2	1.350 (5)	C7—N2	1.456 (5)
C3—C5	1.488 (6)	C7—H7A	0.9800
C4—H4A	0.9800	C7—H7B	0.9800
C4—H4B	0.9800	C7—H7C	0.9800
C4—H4C	0.9800	N1—N2	1.361 (4)
I1—I2—I3	177.099 (12)	H5A—C5—H5C	109.5
N1—C1—C2	107.1 (4)	H5B—C5—H5C	109.5
N1—C1—C4	122.8 (4)	N1—C6—H6A	109.5
C2—C1—C4	130.1 (4)	N1—C6—H6B	109.5
C3—C2—C1	108.0 (4)	H6A—C6—H6B	109.5
C3—C2—H2	126.0	N1—C6—H6C	109.5
C1—C2—H2	126.0	H6A—C6—H6C	109.5
N2—C3—C2	107.1 (4)	H6B—C6—H6C	109.5
N2—C3—C5	122.0 (4)	N2—C7—H7A	109.5
C2—C3—C5	130.8 (4)	N2—C7—H7B	109.5
C1—C4—H4A	109.5	H7A—C7—H7B	109.5
C1—C4—H4B	109.5	N2—C7—H7C	109.5
H4A—C4—H4B	109.5	H7A—C7—H7C	109.5
C1—C4—H4C	109.5	H7B—C7—H7C	109.5
H4A—C4—H4C	109.5	C1—N1—N2	109.2 (3)
H4B—C4—H4C	109.5	C1—N1—C6	128.9 (4)
C3—C5—H5A	109.5	N2—N1—C6	121.9 (3)
C3—C5—H5B	109.5	C3—N2—N1	108.5 (3)
H5A—C5—H5B	109.5	C3—N2—C7	129.1 (4)
C3—C5—H5C	109.5	N1—N2—C7	122.3 (3)
N1—C1—C2—C3	−0.3 (5)	C2—C3—N2—N1	−0.3 (4)
C4—C1—C2—C3	179.5 (4)	C5—C3—N2—N1	179.4 (4)
C1—C2—C3—N2	0.4 (4)	C2—C3—N2—C7	−178.6 (4)
C1—C2—C3—C5	−179.3 (4)	C5—C3—N2—C7	1.1 (6)
C2—C1—N1—N2	0.2 (4)	C1—N1—N2—C3	0.1 (4)
C4—C1—N1—N2	−179.7 (4)	C6—N1—N2—C3	179.3 (3)
C2—C1—N1—C6	−179.0 (4)	C1—N1—N2—C7	178.6 (3)
C4—C1—N1—C6	1.1 (6)	C6—N1—N2—C7	−2.2 (5)