Structure determination and Hirshfeld surface analysis of new cocrystal and salt forms of 5-amino­tetra­zole with hy­droxy- and nitro-substituted carb­oxy­lic acids

Nirmal Ram, J.S.; Sathya, U.; Gomathi, S.; Cordes, D.B.

doi:10.1107/S2053229622006519

Structure determination and Hirshfeld surface analysis of new cocrystal and salt forms of 5-aminotetrazole with hydroxy- and nitro-substituted carboxylic acids

J. S. Nirmal Ram, U. Sathya, S. Gomathi and D. B. Cordes

Two new crystalline solids, namely, 5-aminotetrazole–3,5-dihydroxybenzoic acid–water (1/4/6), CH₃N₅·4C₇H₆O₄·6H₂O (I), and 5-aminotetrazolium 3,5-dinitrosalicylate, CH₄N₅⁺·C₇H₃N₂O₇⁻ (II), have been synthesized and characterized by single-crystal X-ray diffraction and Hirshfeld surface analysis. The crystal packing arrangements of I and II are governed by N—H

O and O—H

O hydrogen-bonding interactions. In cocrystal I, adjacent acid molecules are linked through O—H

O hydrogen bonds, forming a dimer with an R₂²(8) motif. In salt II, the tetrazolium cation and acid anion are linked through N—H

O hydrogen bonds to also form a dimer with an R₂²(8) motif. Further N—H

O and O—H

O hydrogen bonds help to stabilize the crystal packing, along with aromatic π–π stacking interactions in I and carbonyl

π interactions in II. The Hirshfeld surface analysis and fingerprint plots reveal that O

H/H

O interactions contribute 34.4% of the total interactions in the crystal packing of cocrystal I and 36.7% in salt II.

Keywords: 5-aminotetrazole; intermolecular interaction; crystal structure; comparative analysis; Hirshfeld surface analysis; two-dimensional fingerprint plot.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229622006519/zo3022sup1.cif Contains datablocks I, II, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229622006519/zo3022Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229622006519/zo3022IIsup3.hkl Contains datablock II
	Portable Document Format (PDF) file https://doi.org/10.1107/S2053229622006519/zo3022sup4.pdf Additional figure
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229622006519/zo3022Isup5.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229622006519/zo3022IIsup6.cml Supplementary material

CCDC references: 2181468; 2181467

Computing details top

For both structures, data collection: CrystalClear-SM Expert (Rigaku, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2019); data reduction: CrysAlis PRO (Rigaku OD, 2019); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020), PLATON (Spek, 2020) and POVRay (Cason, 2004); software used to prepare material for publication: enCIFer (Allen et al., 2004).

5-Aminotetrazole–3,5-dihydroxybenzoic acid–water (1/4/6) (I) top

Crystal data top

CH₃N₅·4C₇H₆O₄·6H₂O	F(000) = 1696
M_r = 809.65	D_x = 1.499 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 9.4539 (6) Å	Cell parameters from 5950 reflections
b = 29.9892 (15) Å	θ = 2.1–31.9°
c = 13.1934 (10) Å	µ = 0.13 mm⁻¹
β = 106.454 (7)°	T = 173 K
V = 3587.3 (4) Å³	Prism, colourless
Z = 4	0.21 × 0.14 × 0.04 mm

Data collection top

Rigaku SCXMini diffractometer	11003 independent reflections
Radiation source: Sealed Tube	5256 reflections with I > 2σ(I)
SHINE graphite Monochromator monochromator	R_int = 0.060
ω scans	θ_max = 31.8°, θ_min = 2.1°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2019)	h = −13→13
T_min = 0.993, T_max = 1.000	k = −41→43
22166 measured reflections	l = −19→18

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.066	w = 1/[σ²(F_o²) + (0.0595P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.152	(Δ/σ)_max = 0.001
S = 0.98	Δρ_max = 0.37 e Å⁻³
11003 reflections	Δρ_min = −0.28 e Å⁻³
601 parameters	Absolute structure: Flack x determined using 1769 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
30 restraints	Absolute structure parameter: 0.4 (7)
Primary atom site location: dual

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1A	0.9818 (4)	0.67388 (12)	0.6014 (3)	0.0318 (9)
H1A	0.967 (7)	0.7064 (9)	0.606 (5)	0.045 (17)*
O1B	0.2417 (4)	0.26327 (12)	0.6126 (4)	0.0371 (10)
H1B	0.246 (8)	0.2309 (9)	0.620 (6)	0.08 (2)*
O1C	0.2331 (4)	0.29583 (13)	0.3553 (3)	0.0318 (10)
H1C	0.220 (7)	0.2640 (10)	0.366 (5)	0.046 (18)*
O1D	0.4968 (4)	0.70591 (13)	0.3795 (3)	0.0317 (10)
H1D	0.500 (6)	0.7379 (9)	0.386 (4)	0.033 (16)*
O1W	0.8376 (4)	0.37670 (11)	0.5850 (3)	0.0349 (10)
H1WA	0.854 (7)	0.3490 (12)	0.623 (4)	0.052*
H1WB	0.927 (4)	0.3923 (18)	0.590 (5)	0.052*
O2A	0.7568 (4)	0.67594 (12)	0.6255 (3)	0.0275 (9)
O2B	0.4791 (4)	0.26096 (12)	0.6142 (3)	0.0340 (10)
O2C	−0.0008 (4)	0.29331 (14)	0.3633 (3)	0.0325 (10)
O2D	0.7196 (4)	0.70819 (13)	0.3529 (3)	0.0295 (9)
O2W	0.3356 (4)	0.56008 (11)	0.5769 (3)	0.0303 (9)
H2WA	0.430 (4)	0.5468 (18)	0.605 (4)	0.045*
H2WB	0.333 (6)	0.5626 (18)	0.503 (2)	0.045*
O3A	0.6138 (4)	0.51485 (12)	0.6269 (3)	0.0286 (9)
H3A	0.619 (8)	0.4828 (11)	0.612 (6)	0.10 (3)*
O3B	0.6019 (4)	0.42532 (12)	0.5830 (3)	0.0253 (8)
H3B	0.681 (5)	0.4062 (18)	0.576 (5)	0.06 (2)*
O3C	−0.1312 (4)	0.45476 (12)	0.3875 (3)	0.0233 (8)
H3C	−0.132 (6)	0.4857 (9)	0.372 (4)	0.041 (17)*
O3D	0.8514 (4)	0.54398 (12)	0.3372 (3)	0.0228 (8)
H3D	0.929 (5)	0.5651 (16)	0.344 (5)	0.054 (18)*
O3W	0.0805 (4)	0.59265 (14)	0.3484 (4)	0.0481 (12)
H3WA	0.098 (8)	0.6226 (12)	0.376 (5)	0.072*
H3WB	0.141 (6)	0.587 (2)	0.303 (4)	0.072*
O4A	1.1046 (4)	0.51122 (12)	0.5934 (3)	0.0273 (9)
H4A	1.185 (5)	0.5309 (17)	0.598 (5)	0.06 (2)*
O4B	0.1211 (4)	0.42277 (12)	0.6339 (3)	0.0257 (8)
H4B	0.121 (7)	0.4536 (11)	0.609 (5)	0.08 (3)*
O4C	0.3506 (4)	0.45786 (13)	0.3371 (3)	0.0290 (9)
H4C	0.429 (5)	0.4368 (15)	0.348 (4)	0.042 (16)*
O4D	0.3609 (4)	0.54587 (12)	0.3697 (3)	0.0283 (9)
H4D	0.370 (5)	0.5154 (9)	0.360 (4)	0.018 (13)*
O4W	0.6163 (4)	0.32244 (12)	0.2974 (3)	0.0383 (9)
H4WA	0.630 (7)	0.3028 (17)	0.357 (3)	0.058*
H4WB	0.678 (6)	0.3175 (19)	0.254 (4)	0.058*
O5W	0.5802 (4)	0.41320 (13)	0.3215 (3)	0.0375 (10)
H5WA	0.595 (7)	0.3816 (10)	0.329 (5)	0.056*
H5WB	0.675 (4)	0.4263 (19)	0.350 (5)	0.056*
O6W	0.8880 (4)	0.29373 (12)	0.7024 (3)	0.0326 (9)
H6WA	0.983 (4)	0.2883 (19)	0.752 (4)	0.049*
H6WB	0.821 (5)	0.2986 (19)	0.743 (4)	0.049*
N1	0.2806 (5)	0.73205 (14)	0.5353 (4)	0.0304 (10)
H1	0.327 (6)	0.7519 (13)	0.595 (3)	0.034 (16)*
N2	0.1923 (6)	0.74655 (15)	0.4409 (4)	0.0369 (11)
N3	0.1410 (5)	0.71110 (16)	0.3860 (4)	0.0343 (11)
N4	0.1933 (5)	0.67313 (14)	0.4425 (3)	0.0285 (10)
N6	0.3520 (7)	0.66094 (14)	0.6159 (5)	0.0359 (11)
H6E	0.350 (8)	0.6295 (9)	0.605 (6)	0.058 (17)*
H6F	0.428 (5)	0.6748 (17)	0.671 (3)	0.039 (16)*
C1A	0.8643 (6)	0.60517 (12)	0.6113 (5)	0.0175 (8)
C1B	0.3643 (7)	0.33185 (12)	0.6107 (5)	0.0199 (9)
C1C	0.1119 (6)	0.36424 (15)	0.3595 (4)	0.0168 (11)
C1D	0.6124 (6)	0.63694 (17)	0.3643 (4)	0.0184 (11)
C2A	0.7377 (5)	0.58230 (17)	0.6198 (4)	0.0183 (11)
H2A	0.653508	0.598172	0.625794	0.022*
C2B	0.4875 (6)	0.35437 (16)	0.5972 (4)	0.0188 (11)
H2B	0.570536	0.338353	0.589401	0.023*
C2C	−0.0109 (5)	0.38706 (17)	0.3733 (4)	0.0193 (11)
H2C	−0.093365	0.371084	0.382215	0.023*
C2D	0.7350 (5)	0.61467 (17)	0.3530 (4)	0.0184 (11)
H2D	0.819591	0.630798	0.348765	0.022*
C3A	0.7395 (5)	0.53613 (16)	0.6194 (4)	0.0187 (11)
C3B	0.4854 (6)	0.40080 (17)	0.5953 (4)	0.0192 (11)
C3C	−0.0100 (5)	0.43334 (18)	0.3737 (4)	0.0191 (11)
C3D	0.7329 (5)	0.56810 (18)	0.3479 (4)	0.0174 (11)
C4A	0.8617 (6)	0.51269 (12)	0.6098 (4)	0.0187 (8)
H4AA	0.860842	0.481011	0.608923	0.022*
C4B	0.3644 (6)	0.42429 (12)	0.6076 (5)	0.0187 (9)
H4BA	0.364279	0.455967	0.606989	0.022*
C4C	0.1111 (5)	0.45694 (17)	0.3617 (4)	0.0189 (11)
H4CA	0.111134	0.488618	0.362572	0.023*
C4D	0.6090 (6)	0.54441 (17)	0.3532 (4)	0.0193 (11)
H4DA	0.607574	0.512780	0.349269	0.023*
C5	0.2800 (6)	0.68670 (17)	0.5355 (4)	0.0273 (12)
C5A	0.9861 (5)	0.53605 (16)	0.6016 (4)	0.0181 (11)
C5B	0.2427 (6)	0.40082 (17)	0.6209 (4)	0.0187 (11)
C5C	0.2322 (5)	0.43368 (17)	0.3483 (4)	0.0173 (11)
C5D	0.4863 (5)	0.56776 (18)	0.3646 (4)	0.0216 (12)
C6A	0.9873 (6)	0.58229 (16)	0.6013 (4)	0.0165 (11)
H6A	1.071150	0.598085	0.594297	0.020*
C6B	0.2421 (6)	0.35474 (16)	0.6234 (4)	0.0205 (11)
H6B	0.159995	0.338982	0.633608	0.025*
C6C	0.2330 (5)	0.38723 (17)	0.3460 (4)	0.0209 (12)
H6C	0.314904	0.371532	0.335372	0.025*
C6D	0.4875 (5)	0.61409 (17)	0.3712 (4)	0.0182 (11)
H6D	0.404620	0.629780	0.380140	0.022*
C7A	0.8641 (7)	0.65467 (12)	0.6133 (5)	0.0184 (9)
C7B	0.3671 (7)	0.28226 (13)	0.6127 (5)	0.0226 (9)
C7C	0.1086 (6)	0.31442 (16)	0.3592 (4)	0.0221 (12)
C7D	0.6131 (6)	0.68655 (16)	0.3657 (4)	0.0201 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.030 (2)	0.0114 (19)	0.058 (3)	−0.0034 (18)	0.0200 (19)	0.002 (2)
O1B	0.028 (2)	0.0120 (19)	0.071 (3)	−0.0023 (19)	0.015 (2)	0.002 (2)
O1C	0.029 (2)	0.012 (2)	0.056 (3)	0.0010 (17)	0.017 (2)	−0.0002 (19)
O1D	0.026 (2)	0.0123 (19)	0.065 (3)	0.0057 (17)	0.026 (2)	0.0000 (19)
O1W	0.027 (2)	0.0256 (18)	0.055 (3)	0.0030 (18)	0.016 (2)	0.0078 (18)
O2A	0.023 (2)	0.0164 (19)	0.046 (2)	−0.0011 (17)	0.0152 (18)	−0.0029 (19)
O2B	0.029 (2)	0.017 (2)	0.059 (3)	0.0029 (19)	0.017 (2)	0.002 (2)
O2C	0.027 (2)	0.0146 (19)	0.059 (3)	−0.0022 (18)	0.0166 (19)	0.0007 (19)
O2D	0.024 (2)	0.0159 (19)	0.055 (3)	0.0011 (17)	0.0213 (19)	0.0013 (19)
O2W	0.023 (2)	0.0281 (18)	0.041 (2)	0.0025 (17)	0.0116 (18)	0.0082 (17)
O3A	0.021 (2)	0.0172 (19)	0.051 (2)	−0.0030 (17)	0.0164 (18)	−0.0014 (19)
O3B	0.0203 (19)	0.0178 (19)	0.042 (2)	−0.0022 (16)	0.0153 (17)	0.0013 (17)
O3C	0.0168 (18)	0.0155 (19)	0.041 (2)	0.0044 (14)	0.0134 (16)	−0.0018 (17)
O3D	0.0187 (18)	0.0118 (18)	0.040 (2)	0.0003 (15)	0.0109 (16)	−0.0026 (15)
O3W	0.040 (2)	0.034 (2)	0.085 (4)	−0.0143 (19)	0.040 (2)	−0.027 (2)
O4A	0.0180 (19)	0.0153 (19)	0.053 (3)	0.0020 (16)	0.0172 (18)	−0.0008 (18)
O4B	0.0227 (19)	0.0179 (19)	0.039 (2)	0.0036 (16)	0.0133 (17)	0.0024 (17)
O4C	0.0186 (18)	0.0138 (18)	0.059 (3)	−0.0012 (15)	0.0176 (18)	−0.0030 (17)
O4D	0.023 (2)	0.0112 (18)	0.055 (3)	−0.0024 (15)	0.0185 (19)	−0.0017 (17)
O4W	0.040 (2)	0.032 (2)	0.045 (3)	0.0015 (19)	0.017 (2)	0.0029 (19)
O5W	0.024 (2)	0.029 (2)	0.063 (3)	−0.0006 (17)	0.017 (2)	−0.006 (2)
O6W	0.035 (2)	0.031 (2)	0.031 (2)	0.0020 (18)	0.0076 (17)	0.0004 (17)
N1	0.032 (3)	0.028 (2)	0.030 (3)	0.003 (2)	0.007 (2)	−0.003 (2)
N2	0.038 (3)	0.032 (3)	0.037 (3)	0.007 (2)	0.005 (2)	0.002 (2)
N3	0.036 (3)	0.034 (3)	0.033 (2)	−0.002 (2)	0.009 (2)	−0.005 (2)
N4	0.025 (2)	0.029 (2)	0.031 (3)	−0.0017 (19)	0.0075 (19)	−0.004 (2)
N6	0.040 (3)	0.026 (2)	0.035 (3)	−0.002 (3)	0.000 (2)	−0.002 (3)
C1A	0.020 (2)	0.0142 (18)	0.018 (2)	−0.001 (3)	0.0050 (17)	−0.002 (3)
C1B	0.020 (2)	0.0145 (19)	0.024 (2)	−0.001 (3)	0.0040 (18)	−0.001 (3)
C1C	0.019 (3)	0.007 (2)	0.024 (3)	0.002 (2)	0.005 (2)	0.000 (2)
C1D	0.020 (3)	0.015 (3)	0.019 (3)	0.002 (2)	0.003 (2)	0.000 (2)
C2A	0.013 (2)	0.021 (3)	0.022 (3)	0.000 (2)	0.005 (2)	0.000 (2)
C2B	0.015 (3)	0.014 (3)	0.027 (3)	0.002 (2)	0.005 (2)	−0.004 (2)
C2C	0.018 (3)	0.015 (3)	0.025 (3)	0.001 (2)	0.007 (2)	−0.001 (2)
C2D	0.017 (3)	0.012 (3)	0.027 (3)	−0.004 (2)	0.007 (2)	0.001 (2)
C3A	0.018 (3)	0.013 (2)	0.026 (3)	−0.004 (2)	0.006 (2)	0.001 (2)
C3B	0.015 (3)	0.018 (3)	0.024 (3)	−0.001 (2)	0.006 (2)	0.002 (2)
C3C	0.019 (3)	0.019 (3)	0.019 (3)	−0.001 (2)	0.005 (2)	0.002 (2)
C3D	0.015 (3)	0.017 (3)	0.022 (3)	0.004 (2)	0.008 (2)	−0.001 (2)
C4A	0.019 (2)	0.0118 (18)	0.025 (2)	0.002 (3)	0.0058 (17)	0.002 (3)
C4B	0.020 (2)	0.0096 (17)	0.027 (2)	−0.003 (2)	0.0072 (18)	0.002 (3)
C4C	0.023 (3)	0.010 (2)	0.025 (3)	0.003 (2)	0.009 (2)	−0.002 (2)
C4D	0.023 (3)	0.012 (2)	0.023 (3)	−0.001 (2)	0.007 (2)	−0.003 (2)
C5	0.026 (3)	0.029 (3)	0.031 (3)	−0.003 (2)	0.014 (2)	−0.002 (2)
C5A	0.015 (3)	0.018 (3)	0.022 (3)	0.002 (2)	0.005 (2)	−0.001 (2)
C5B	0.019 (3)	0.016 (3)	0.020 (3)	0.005 (2)	0.005 (2)	0.000 (2)
C5C	0.020 (3)	0.013 (3)	0.019 (3)	−0.001 (2)	0.007 (2)	0.000 (2)
C5D	0.018 (3)	0.017 (3)	0.029 (3)	−0.004 (2)	0.006 (2)	−0.002 (2)
C6A	0.017 (3)	0.012 (3)	0.022 (3)	0.000 (2)	0.007 (2)	0.001 (2)
C6B	0.020 (3)	0.017 (3)	0.024 (3)	−0.005 (2)	0.005 (2)	−0.003 (2)
C6C	0.020 (3)	0.014 (3)	0.031 (3)	0.001 (2)	0.010 (2)	0.001 (2)
C6D	0.017 (3)	0.016 (3)	0.022 (3)	0.002 (2)	0.006 (2)	−0.003 (2)
C7A	0.019 (2)	0.0138 (19)	0.023 (2)	0.001 (3)	0.0069 (17)	0.004 (3)
C7B	0.021 (2)	0.0155 (19)	0.032 (3)	−0.002 (3)	0.0083 (19)	−0.003 (3)
C7C	0.026 (3)	0.010 (2)	0.029 (3)	0.001 (2)	0.004 (2)	0.003 (2)
C7D	0.019 (3)	0.017 (3)	0.026 (3)	0.005 (2)	0.009 (2)	−0.001 (2)

Geometric parameters (Å, º) top

O1A—H1A	0.99 (3)	N4—C5	1.332 (6)
O1A—C7A	1.302 (7)	N6—H6E	0.95 (3)
O1B—H1B	0.98 (3)	N6—H6F	0.96 (3)
O1B—C7B	1.315 (7)	N6—C5	1.332 (7)
O1C—H1C	0.98 (3)	C1A—C2A	1.412 (7)
O1C—C7C	1.316 (7)	C1A—C6A	1.388 (7)
O1D—H1D	0.96 (3)	C1A—C7A	1.485 (5)
O1D—C7D	1.301 (6)	C1B—C2B	1.401 (7)
O1W—H1WA	0.96 (3)	C1B—C6B	1.395 (7)
O1W—H1WB	0.95 (3)	C1B—C7B	1.487 (5)
O2A—C7A	1.247 (6)	C1C—C2C	1.404 (7)
O2B—C7B	1.232 (7)	C1C—C6C	1.390 (7)
O2C—C7C	1.227 (6)	C1C—C7C	1.494 (7)
O2D—C7D	1.249 (6)	C1D—C2D	1.381 (7)
O2W—H2WA	0.95 (3)	C1D—C6D	1.390 (7)
O2W—H2WB	0.97 (3)	C1D—C7D	1.488 (7)
O3A—H3A	0.99 (3)	C2A—H2A	0.9500
O3A—C3A	1.377 (6)	C2A—C3A	1.385 (7)
O3B—H3B	0.96 (3)	C2B—H2B	0.9500
O3B—C3B	1.372 (6)	C2B—C3B	1.393 (7)
O3C—H3C	0.95 (3)	C2C—H2C	0.9500
O3C—C3C	1.370 (6)	C2C—C3C	1.388 (7)
O3D—H3D	0.95 (3)	C2D—H2D	0.9500
O3D—C3D	1.374 (6)	C2D—C3D	1.398 (7)
O3W—H3WA	0.97 (3)	C3A—C4A	1.388 (7)
O3W—H3WB	0.95 (3)	C3B—C4B	1.392 (7)
O4A—H4A	0.95 (3)	C3C—C4C	1.392 (7)
O4A—C5A	1.375 (6)	C3D—C4D	1.389 (7)
O4B—H4B	0.98 (3)	C4A—H4AA	0.9500
O4B—C5B	1.377 (6)	C4A—C5A	1.400 (7)
O4C—H4C	0.95 (3)	C4B—H4BA	0.9500
O4C—C5C	1.377 (6)	C4B—C5B	1.402 (7)
O4D—H4D	0.93 (2)	C4C—H4CA	0.9500
O4D—C5D	1.373 (6)	C4C—C5C	1.394 (7)
O4W—H4WA	0.97 (3)	C4D—H4DA	0.9500
O4W—H4WB	0.94 (3)	C4D—C5D	1.398 (7)
O5W—H5WA	0.96 (3)	C5A—C6A	1.387 (7)
O5W—H5WB	0.95 (3)	C5B—C6B	1.382 (7)
O6W—H6WA	0.96 (3)	C5C—C6C	1.393 (7)
O6W—H6WB	0.96 (3)	C5D—C6D	1.392 (7)
N1—H1	0.98 (3)	C6A—H6A	0.9500
N1—N2	1.359 (6)	C6B—H6B	0.9500
N1—C5	1.360 (6)	C6C—H6C	0.9500
N2—N3	1.300 (6)	C6D—H6D	0.9500
N3—N4	1.374 (6)

C7A—O1A—H1A	107 (4)	O3C—C3C—C2C	117.7 (4)
C7B—O1B—H1B	115 (5)	O3C—C3C—C4C	121.5 (5)
C7C—O1C—H1C	105 (4)	C2C—C3C—C4C	120.8 (5)
C7D—O1D—H1D	117 (3)	O3D—C3D—C2D	122.0 (5)
H1WA—O1W—H1WB	112 (5)	O3D—C3D—C4D	117.4 (5)
H2WA—O2W—H2WB	100 (5)	C4D—C3D—C2D	120.6 (5)
C3A—O3A—H3A	110 (4)	C3A—C4A—H4AA	120.2
C3B—O3B—H3B	111 (4)	C3A—C4A—C5A	119.5 (3)
C3C—O3C—H3C	113 (3)	C5A—C4A—H4AA	120.2
C3D—O3D—H3D	105 (4)	C3B—C4B—H4BA	120.3
H3WA—O3W—H3WB	109 (6)	C3B—C4B—C5B	119.4 (3)
C5A—O4A—H4A	108 (4)	C5B—C4B—H4BA	120.3
C5B—O4B—H4B	109 (4)	C3C—C4C—H4CA	120.3
C5C—O4C—H4C	105 (3)	C3C—C4C—C5C	119.4 (4)
C5D—O4D—H4D	110 (3)	C5C—C4C—H4CA	120.3
H4WA—O4W—H4WB	116 (4)	C3D—C4D—H4DA	120.5
H5WA—O5W—H5WB	106 (5)	C3D—C4D—C5D	119.1 (4)
H6WA—O6W—H6WB	107 (5)	C5D—C4D—H4DA	120.5
N2—N1—H1	124 (3)	N4—C5—N1	107.8 (5)
N2—N1—C5	108.7 (4)	N4—C5—N6	126.8 (5)
C5—N1—H1	127 (3)	N6—C5—N1	125.4 (5)
N3—N2—N1	106.5 (4)	O4A—C5A—C4A	117.2 (4)
N2—N3—N4	110.8 (4)	O4A—C5A—C6A	122.3 (5)
C5—N4—N3	106.2 (4)	C6A—C5A—C4A	120.6 (5)
H6E—N6—H6F	121 (6)	O4B—C5B—C4B	121.3 (4)
C5—N6—H6E	118 (4)	O4B—C5B—C6B	117.8 (5)
C5—N6—H6F	117 (3)	C6B—C5B—C4B	120.9 (5)
C2A—C1A—C7A	118.6 (5)	O4C—C5C—C4C	118.2 (4)
C6A—C1A—C2A	121.3 (4)	O4C—C5C—C6C	121.0 (5)
C6A—C1A—C7A	120.1 (5)	C6C—C5C—C4C	120.8 (5)
C2B—C1B—C7B	118.2 (5)	O4D—C5D—C4D	121.3 (5)
C6B—C1B—C2B	121.7 (3)	O4D—C5D—C6D	117.8 (5)
C6B—C1B—C7B	120.1 (5)	C6D—C5D—C4D	120.9 (5)
C2C—C1C—C7C	118.0 (5)	C1A—C6A—H6A	120.5
C6C—C1C—C2C	121.1 (4)	C5A—C6A—C1A	119.1 (5)
C6C—C1C—C7C	120.9 (5)	C5A—C6A—H6A	120.5
C2D—C1D—C6D	121.5 (4)	C1B—C6B—H6B	120.7
C2D—C1D—C7D	119.0 (4)	C5B—C6B—C1B	118.7 (5)
C6D—C1D—C7D	119.5 (5)	C5B—C6B—H6B	120.7
C1A—C2A—H2A	120.8	C1C—C6C—C5C	118.9 (5)
C3A—C2A—C1A	118.3 (5)	C1C—C6C—H6C	120.5
C3A—C2A—H2A	120.8	C5C—C6C—H6C	120.5
C1B—C2B—H2B	120.8	C1D—C6D—C5D	118.7 (5)
C3B—C2B—C1B	118.4 (5)	C1D—C6D—H6D	120.7
C3B—C2B—H2B	120.8	C5D—C6D—H6D	120.7
C1C—C2C—H2C	120.6	O1A—C7A—C1A	115.8 (5)
C3C—C2C—C1C	118.9 (5)	O2A—C7A—O1A	122.9 (4)
C3C—C2C—H2C	120.6	O2A—C7A—C1A	121.3 (5)
C1D—C2D—H2D	120.4	O1B—C7B—C1B	114.9 (5)
C1D—C2D—C3D	119.2 (5)	O2B—C7B—O1B	123.1 (4)
C3D—C2D—H2D	120.4	O2B—C7B—C1B	121.9 (5)
O3A—C3A—C2A	116.8 (5)	O1C—C7C—C1C	113.9 (5)
O3A—C3A—C4A	121.9 (4)	O2C—C7C—O1C	123.9 (5)
C2A—C3A—C4A	121.2 (5)	O2C—C7C—C1C	122.2 (5)
O3B—C3B—C2B	122.0 (5)	O1D—C7D—C1D	116.6 (5)
O3B—C3B—C4B	117.2 (4)	O2D—C7D—O1D	122.2 (5)
C4B—C3B—C2B	120.8 (5)	O2D—C7D—C1D	121.2 (5)

O3A—C3A—C4A—C5A	179.5 (4)	C2D—C1D—C7D—O2D	2.8 (8)
O3B—C3B—C4B—C5B	−179.7 (4)	C2D—C3D—C4D—C5D	−0.4 (8)
O3C—C3C—C4C—C5C	179.7 (4)	C3A—C4A—C5A—O4A	179.4 (4)
O3D—C3D—C4D—C5D	179.7 (4)	C3A—C4A—C5A—C6A	−1.0 (9)
O4A—C5A—C6A—C1A	−179.1 (4)	C3B—C4B—C5B—O4B	179.7 (4)
O4B—C5B—C6B—C1B	−179.9 (5)	C3B—C4B—C5B—C6B	0.9 (9)
O4C—C5C—C6C—C1C	178.9 (4)	C3C—C4C—C5C—O4C	−179.7 (4)
O4D—C5D—C6D—C1D	−178.9 (4)	C3C—C4C—C5C—C6C	0.5 (8)
N1—N2—N3—N4	0.3 (5)	C3D—C4D—C5D—O4D	179.6 (5)
N2—N1—C5—N4	0.4 (5)	C3D—C4D—C5D—C6D	−0.4 (8)
N2—N1—C5—N6	−178.6 (5)	C4A—C5A—C6A—C1A	1.2 (8)
N2—N3—N4—C5	0.0 (5)	C4B—C5B—C6B—C1B	−1.0 (9)
N3—N4—C5—N1	−0.2 (5)	C4C—C5C—C6C—C1C	−1.3 (8)
N3—N4—C5—N6	178.7 (6)	C4D—C5D—C6D—C1D	1.1 (8)
C1A—C2A—C3A—O3A	−179.5 (5)	C5—N1—N2—N3	−0.4 (5)
C1A—C2A—C3A—C4A	−0.5 (9)	C6A—C1A—C2A—C3A	0.8 (9)
C1B—C2B—C3B—O3B	179.6 (4)	C6A—C1A—C7A—O1A	2.4 (8)
C1B—C2B—C3B—C4B	0.6 (9)	C6A—C1A—C7A—O2A	−177.8 (5)
C1C—C2C—C3C—O3C	−179.9 (4)	C6B—C1B—C2B—C3B	−0.7 (9)
C1C—C2C—C3C—C4C	−0.6 (8)	C6B—C1B—C7B—O1B	8.8 (9)
C1D—C2D—C3D—O3D	−179.6 (4)	C6B—C1B—C7B—O2B	−171.4 (5)
C1D—C2D—C3D—C4D	0.5 (8)	C6C—C1C—C2C—C3C	−0.2 (7)
C2A—C1A—C6A—C5A	−1.1 (9)	C6C—C1C—C7C—O1C	6.0 (8)
C2A—C1A—C7A—O1A	−177.7 (5)	C6C—C1C—C7C—O2C	−174.6 (5)
C2A—C1A—C7A—O2A	2.1 (9)	C6D—C1D—C2D—C3D	0.3 (8)
C2A—C3A—C4A—C5A	0.6 (9)	C6D—C1D—C7D—O1D	3.8 (7)
C2B—C1B—C6B—C5B	0.9 (9)	C6D—C1D—C7D—O2D	−175.3 (5)
C2B—C1B—C7B—O1B	−172.0 (5)	C7A—C1A—C2A—C3A	−179.1 (5)
C2B—C1B—C7B—O2B	7.9 (9)	C7A—C1A—C6A—C5A	178.8 (5)
C2B—C3B—C4B—C5B	−0.7 (9)	C7B—C1B—C2B—C3B	−180.0 (5)
C2C—C1C—C6C—C5C	1.2 (8)	C7B—C1B—C6B—C5B	−179.8 (5)
C2C—C1C—C7C—O1C	−174.3 (5)	C7C—C1C—C2C—C3C	−179.9 (5)
C2C—C1C—C7C—O2C	5.1 (8)	C7C—C1C—C6C—C5C	−179.1 (5)
C2C—C3C—C4C—C5C	0.5 (8)	C7D—C1D—C2D—C3D	−177.7 (5)
C2D—C1D—C6D—C5D	−1.1 (8)	C7D—C1D—C6D—C5D	177.0 (5)
C2D—C1D—C7D—O1D	−178.2 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O2Bⁱ	0.99 (3)	1.64 (3)	2.617 (5)	168 (6)
O1B—H1B···O2Aⁱⁱ	0.98 (3)	1.65 (3)	2.626 (5)	177 (7)
O1C—H1C···O2Dⁱⁱ	0.98 (3)	1.68 (3)	2.631 (5)	163 (5)
O1D—H1D···O2Cⁱ	0.96 (3)	1.69 (3)	2.630 (5)	165 (5)
O1W—H1WA···O6W	0.96 (3)	1.94 (3)	2.899 (5)	179 (5)
O1W—H1WB···O4Bⁱⁱⁱ	0.95 (3)	1.98 (3)	2.920 (5)	167 (5)
O2W—H2WA···O3A	0.95 (3)	1.93 (3)	2.865 (5)	166 (5)
O2W—H2WB···O4D	0.97 (3)	1.92 (3)	2.843 (5)	158 (5)
O3A—H3A···O3B	0.99 (3)	1.76 (3)	2.743 (5)	172 (7)
O3B—H3B···O1W	0.96 (3)	1.70 (3)	2.657 (5)	170 (6)
O3C—H3C···O3D^iv	0.95 (3)	1.80 (3)	2.750 (4)	175 (5)
O3D—H3D···O3Wⁱⁱⁱ	0.95 (3)	1.64 (3)	2.582 (5)	168 (6)
O3W—H3WA···N3	0.97 (3)	2.68 (3)	3.610 (6)	161 (6)
O3W—H3WA···N4	0.97 (3)	1.85 (3)	2.784 (6)	162 (6)
O3W—H3WB···O4B^v	0.95 (3)	2.21 (5)	2.998 (6)	140 (5)
O3W—H3WB···O4D	0.95 (3)	2.37 (6)	2.942 (5)	119 (5)
O4A—H4A···O2Wⁱⁱⁱ	0.95 (3)	1.76 (3)	2.690 (5)	166 (6)
O4B—H4B···O4A^iv	0.98 (3)	1.74 (3)	2.701 (5)	165 (6)
O4C—H4C···O5W	0.95 (3)	1.71 (3)	2.607 (5)	154 (5)
O4D—H4D···O4C	0.93 (2)	1.75 (3)	2.672 (4)	169 (4)
O4W—H4WA···N2^vi	0.97 (3)	2.01 (4)	2.918 (6)	156 (5)
O4W—H4WB···O2A^v	0.94 (3)	2.04 (3)	2.936 (6)	158 (5)
O5W—H5WA···O4W	0.96 (3)	1.85 (3)	2.773 (5)	162 (6)
O5W—H5WB···O3Cⁱⁱⁱ	0.95 (3)	1.95 (3)	2.901 (5)	172 (6)
O6W—H6WA···N3^vii	0.96 (3)	1.97 (3)	2.885 (6)	159 (5)
O6W—H6WB···O2D^viii	0.96 (3)	1.95 (3)	2.876 (5)	161 (5)
N1—H1···O6W^ix	0.98 (3)	1.86 (3)	2.837 (6)	172 (5)
N6—H6E···O2W	0.95 (3)	2.11 (3)	3.065 (5)	177 (6)
N6—H6F···O4W^viii	0.96 (3)	2.07 (3)	2.973 (7)	157 (5)

Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x−1/2, y−1/2, z; (iii) x+1, y, z; (iv) x−1, y, z; (v) x, −y+1, z−1/2; (vi) x+1/2, y−1/2, z; (vii) x+1, −y+1, z+1/2; (viii) x, −y+1, z+1/2; (ix) x−1/2, y+1/2, z.

5-Aminotetrazolium 3,5-dinitrosalicylate (II) top

Crystal data top

CH₄N₅⁺·C₇H₃N₂O₇⁻	F(000) = 640
M_r = 313.21	D_x = 1.753 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 6.2591 (3) Å	Cell parameters from 7845 reflections
b = 11.1312 (5) Å	θ = 6.5–68.1°
c = 17.2257 (9) Å	µ = 1.37 mm⁻¹
β = 98.646 (5)°	T = 173 K
V = 1186.50 (10) Å³	Plate, yellow
Z = 4	0.07 × 0.03 × 0.01 mm

Data collection top

Rigaku XtaLAB P100K diffractometer	4182 independent reflections
Radiation source: Rotating Anode, Rigaku MM-007HF	3644 reflections with I > 2σ(I)
Rigaku Osmic Confocal Optical System monochromator	R_int = 0.041
ω and φ scans	θ_max = 68.3°, θ_min = 4.8°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2019)	h = −7→7
T_min = 0.860, T_max = 1.000	k = −13→13
4182 measured reflections	l = −20→20

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.041	w = 1/[σ²(F_o²) + (0.0876P)² + 0.0468P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.114	(Δ/σ)_max = 0.001
S = 1.04	Δρ_max = 0.46 e Å⁻³
4182 reflections	Δρ_min = −0.43 e Å⁻³
221 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
6 restraints	Extinction coefficient: 0.015 (2)
Primary atom site location: dual

Special details top

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.2093 (3)	0.53433 (10)	0.31038 (7)	0.0508 (4)
O2	0.22700 (19)	0.40435 (9)	0.40980 (7)	0.0342 (3)
O3	0.3059 (3)	0.57855 (12)	0.68383 (7)	0.0507 (4)
O4	0.2069 (2)	0.76263 (12)	0.69133 (7)	0.0501 (4)
O5	0.2538 (3)	1.03140 (11)	0.47320 (8)	0.0549 (4)
O6	0.2542 (3)	0.95489 (11)	0.35884 (8)	0.0516 (4)
O7	0.24886 (18)	0.47913 (9)	0.54500 (6)	0.0317 (3)
H7	0.246 (4)	0.4277 (15)	0.4975 (8)	0.061 (7)*
N1	0.2817 (2)	0.18681 (13)	0.16865 (9)	0.0346 (3)
H1	0.299 (3)	0.1046 (13)	0.1548 (14)	0.055 (6)*
N2	0.2682 (2)	0.26852 (14)	0.10881 (9)	0.0388 (4)
N3	0.2448 (2)	0.37131 (13)	0.13805 (8)	0.0386 (4)
N4	0.2429 (2)	0.35865 (12)	0.21645 (8)	0.0341 (3)
H4	0.232 (3)	0.4274 (16)	0.2521 (12)	0.053 (6)*
N6	0.2792 (3)	0.19860 (13)	0.30761 (9)	0.0399 (4)
H6A	0.267 (3)	0.1158 (12)	0.3165 (12)	0.047 (6)*
H6B	0.254 (3)	0.2536 (15)	0.3472 (9)	0.034 (5)*
N12	0.2529 (2)	0.94559 (12)	0.42991 (9)	0.0344 (3)
N13	0.2538 (2)	0.67665 (12)	0.65356 (8)	0.0350 (4)
C5	0.2663 (3)	0.24353 (14)	0.23571 (10)	0.0304 (4)
C7	0.2489 (2)	0.59091 (13)	0.51941 (9)	0.0268 (3)
C8	0.2522 (2)	0.69166 (15)	0.56911 (9)	0.0293 (4)
C9	0.2516 (2)	0.80802 (14)	0.54100 (9)	0.0302 (4)
H9	0.252148	0.874795	0.575371	0.036*
C10	0.2504 (2)	0.82423 (13)	0.46158 (9)	0.0288 (4)
C11	0.2430 (2)	0.72878 (13)	0.40960 (9)	0.0281 (4)
H11	0.240017	0.742847	0.355051	0.034*
C12	0.2401 (2)	0.61341 (13)	0.43800 (9)	0.0267 (3)
C13	0.2250 (3)	0.51070 (14)	0.38150 (9)	0.0315 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1058 (11)	0.0227 (6)	0.0250 (6)	0.0047 (6)	0.0131 (7)	−0.0003 (5)
O2	0.0542 (7)	0.0206 (6)	0.0285 (6)	0.0000 (4)	0.0088 (5)	0.0009 (4)
O3	0.0854 (10)	0.0397 (7)	0.0262 (7)	0.0010 (6)	0.0053 (6)	0.0057 (5)
O4	0.0807 (10)	0.0435 (8)	0.0294 (7)	0.0012 (6)	0.0184 (6)	−0.0085 (5)
O5	0.1030 (12)	0.0233 (7)	0.0395 (7)	−0.0016 (6)	0.0141 (7)	−0.0070 (5)
O6	0.1007 (11)	0.0271 (6)	0.0286 (7)	−0.0019 (6)	0.0145 (7)	0.0046 (5)
O7	0.0470 (7)	0.0233 (6)	0.0248 (6)	−0.0010 (4)	0.0056 (5)	0.0046 (4)
N1	0.0419 (7)	0.0285 (7)	0.0334 (7)	0.0007 (5)	0.0055 (6)	−0.0062 (6)
N2	0.0491 (8)	0.0383 (8)	0.0293 (8)	−0.0001 (6)	0.0066 (6)	−0.0064 (6)
N3	0.0536 (9)	0.0368 (8)	0.0254 (7)	−0.0006 (6)	0.0059 (6)	0.0001 (6)
N4	0.0538 (8)	0.0257 (7)	0.0232 (7)	−0.0002 (6)	0.0070 (6)	−0.0017 (5)
N6	0.0611 (9)	0.0242 (7)	0.0349 (8)	0.0003 (6)	0.0086 (7)	0.0033 (6)
N12	0.0500 (8)	0.0225 (7)	0.0303 (8)	−0.0012 (5)	0.0051 (6)	−0.0009 (5)
N13	0.0473 (8)	0.0349 (8)	0.0231 (7)	−0.0045 (6)	0.0065 (6)	−0.0026 (5)
C5	0.0349 (8)	0.0245 (7)	0.0316 (9)	−0.0019 (6)	0.0050 (6)	−0.0050 (6)
C7	0.0309 (7)	0.0246 (8)	0.0251 (8)	−0.0008 (5)	0.0046 (6)	0.0014 (6)
C8	0.0346 (8)	0.0312 (8)	0.0224 (7)	−0.0018 (6)	0.0050 (6)	−0.0015 (6)
C9	0.0370 (8)	0.0271 (8)	0.0265 (8)	−0.0012 (6)	0.0053 (6)	−0.0060 (6)
C10	0.0369 (8)	0.0218 (8)	0.0278 (8)	−0.0013 (5)	0.0057 (6)	0.0001 (6)
C11	0.0362 (8)	0.0245 (8)	0.0240 (8)	−0.0003 (6)	0.0061 (6)	−0.0003 (6)
C12	0.0332 (8)	0.0239 (8)	0.0233 (8)	0.0002 (5)	0.0053 (6)	0.0008 (6)
C13	0.0474 (9)	0.0231 (7)	0.0243 (8)	0.0005 (6)	0.0064 (7)	0.0003 (6)

Geometric parameters (Å, º) top

O1—C13	1.242 (2)	N6—H6A	0.940 (13)
O2—C13	1.2796 (19)	N6—H6B	0.947 (12)
O3—N13	1.2327 (19)	N6—C5	1.327 (2)
O4—N13	1.2176 (19)	N12—C10	1.458 (2)
O5—N12	1.2113 (18)	N13—C8	1.463 (2)
O6—N12	1.230 (2)	C7—C8	1.409 (2)
O7—H7	0.997 (7)	C7—C12	1.417 (2)
O7—C7	1.3200 (18)	C8—C9	1.383 (2)
N1—H1	0.956 (13)	C9—H9	0.9500
N1—N2	1.368 (2)	C9—C10	1.379 (2)
N1—C5	1.333 (2)	C10—C11	1.386 (2)
N2—N3	1.267 (2)	C11—H11	0.9500
N3—N4	1.360 (2)	C11—C12	1.375 (2)
N4—H4	0.989 (12)	C12—C13	1.495 (2)
N4—C5	1.326 (2)

C7—O7—H7	105.5 (12)	O7—C7—C8	123.23 (14)
N2—N1—H1	116.4 (15)	O7—C7—C12	119.67 (14)
C5—N1—H1	134.1 (15)	C8—C7—C12	117.09 (13)
C5—N1—N2	109.50 (14)	C7—C8—N13	120.70 (14)
N3—N2—N1	107.38 (13)	C9—C8—N13	117.05 (14)
N2—N3—N4	108.66 (14)	C9—C8—C7	122.25 (14)
N3—N4—H4	123.2 (14)	C8—C9—H9	121.0
C5—N4—N3	109.36 (13)	C10—C9—C8	118.00 (15)
C5—N4—H4	127.4 (14)	C10—C9—H9	121.0
H6A—N6—H6B	119.4 (18)	C9—C10—N12	119.59 (14)
C5—N6—H6A	121.8 (13)	C9—C10—C11	122.37 (14)
C5—N6—H6B	115.8 (12)	C11—C10—N12	118.03 (14)
O5—N12—O6	123.11 (14)	C10—C11—H11	120.4
O5—N12—C10	119.98 (14)	C12—C11—C10	119.14 (14)
O6—N12—C10	116.91 (13)	C12—C11—H11	120.4
O3—N13—C8	118.92 (14)	C7—C12—C13	119.89 (13)
O4—N13—O3	122.68 (15)	C11—C12—C7	121.08 (14)
O4—N13—C8	118.38 (14)	C11—C12—C13	119.03 (14)
N4—C5—N1	105.11 (15)	O1—C13—O2	124.49 (14)
N4—C5—N6	125.92 (15)	O1—C13—C12	117.90 (14)
N6—C5—N1	128.93 (16)	O2—C13—C12	117.60 (13)

O3—N13—C8—C7	17.9 (2)	N12—C10—C11—C12	−179.87 (14)
O3—N13—C8—C9	−162.77 (15)	N13—C8—C9—C10	179.93 (13)
O4—N13—C8—C7	−163.36 (16)	C5—N1—N2—N3	−0.14 (19)
O4—N13—C8—C9	16.0 (2)	C7—C8—C9—C10	−0.8 (2)
O5—N12—C10—C9	−0.8 (3)	C7—C12—C13—O1	177.30 (15)
O5—N12—C10—C11	178.14 (16)	C7—C12—C13—O2	−2.0 (2)
O6—N12—C10—C9	179.14 (15)	C8—C7—C12—C11	2.4 (2)
O6—N12—C10—C11	−1.9 (2)	C8—C7—C12—C13	−176.95 (14)
O7—C7—C8—N13	−0.6 (2)	C8—C9—C10—N12	−179.13 (14)
O7—C7—C8—C9	−179.84 (14)	C8—C9—C10—C11	2.0 (2)
O7—C7—C12—C11	−179.06 (14)	C9—C10—C11—C12	−1.0 (2)
O7—C7—C12—C13	1.6 (2)	C10—C11—C12—C7	−1.3 (2)
N1—N2—N3—N4	0.02 (19)	C10—C11—C12—C13	178.08 (14)
N2—N1—C5—N4	0.20 (18)	C11—C12—C13—O1	−2.1 (2)
N2—N1—C5—N6	−177.39 (16)	C11—C12—C13—O2	178.63 (15)
N2—N3—N4—C5	0.1 (2)	C12—C7—C8—N13	177.89 (13)
N3—N4—C5—N1	−0.19 (18)	C12—C7—C8—C9	−1.4 (2)
N3—N4—C5—N6	177.50 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7···O2	1.00 (1)	1.52 (1)	2.4576 (15)	155 (2)
N1—H1···O3ⁱ	0.96 (1)	2.10 (2)	2.967 (2)	150 (2)
N1—H1···O7ⁱ	0.96 (1)	2.09 (2)	2.8033 (17)	130 (2)
N4—H4···O1	0.99 (1)	1.58 (1)	2.5668 (17)	178 (2)
N6—H6A···O6ⁱⁱ	0.94 (1)	1.94 (1)	2.8643 (19)	167 (2)
N6—H6B···O2	0.95 (1)	2.02 (1)	2.9367 (19)	164 (2)

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

Crystallographic and interaction details of compounds I and II and some known related structures top

Ligand	Acid	Space group; unit-cell parameters (Å, °)	Primary interaction	Graph-set motif	Motif type	Secondary interaction	Graph-set motif	Motif type
5-Aminotertrazole	Hydrochloride'	Pbca; a = 7.63530 (10), b = 11.3272 (2), c = 12.8959	N—H···Cl	R₂¹(6)	I	N—H···Cl, N—H···O	R₄²(10) and R₄³(10)	VII and VIII
	Hydrobromide	Pbcm; a = 6.5473 (2), b = 7.7505 (2), c = 11.5478 (4)	N—H···Br	R₂¹(6)	I	N—H···Br, O—H···Br	R₆⁴(15)	VI
	Iodide	Pbcm; a = 6.84660 (10), b = 7.8770 (2), c = 12.0820 (2)				N—H···I, O—H···I	R₆⁴(15)	VI
	Nitrate	P2₁/c; a = 10.5493 (8), b = 3.4556 (4), c = 14.606 (1), β = 90.548 (9)	N—H···O	R₂²(6)	II	N—H···O	R₂¹(4) and R₂²(4)	IX
	Perchlorate	P2₁/n; a = 5.26150 (10), b = 8.5311 (2), c = 21.4870 (4), β = 96.1273 (13)	N—H···N	R₂²(6)	III	N—H···O	R₂²(8)	XII
	Picrate	C2/c; a = 25.4959 (13), b = 6.1793 (3), c = 14.5863 (8), β = 98.069 (1)	N—H···O	R₂¹(6)	I	N—H···O	R₁²(6) and R₁²(4)	X and XI
	3,5-Dihydroxybenzoic acid, I	Cc; a = 9.4539 (6), b = 29.9892 (15), c = 13.1934 (10), β = 106.454 (7)	N—H···O, O—H···O	R₄⁴(11)	V
	3,5-Dinitrosalycylic acid, II	P2₁/c; a = 6.2591 (3), b = 11.1312 (5), c = 17.2257 (9), β = 98.646 (5)	N—H···O	R₂²(8)	IV	N—H···O	R₁²(6) and R₆⁶(31)	X and XIII

A comparison of the hydrogen-bond geometry (Å, °) of AT in different solid forms top

Compound	D—H···A	D···A	D—H···A
Aminotetrazolium bromide	N—H···Br	3.4091 (5)	154 (2)
Aminotetrazolium iodide	N—H···I	3.588 (2)	161 (4)
Aminotetrazolium chloride	N—H···Cl	3.242 (2)	170 (2)
Aminotetrazole with solvents	N—H···O	2.772 (2)	152 (2)
	N—H···O	2.755 (2)	146 (2)
	N—H···O	2.667 (2)	165 (2)
N—H···N interaction in aminotetrazole	N—H···N	2.819 (2)	159 (2)
	N—H···N	2.861 (2)	150 (2)
	N—H···N	3.073 (2)	125 (2)
	N—H···N	3.074 (2)	111 (1)
	N—H···N	3.026 (2)	125 (2)
	N—H···N	3.039 (2)	114 (2)
	N—H···N	3.068 (3)	113 (2)
	N—H···N	3.185 (3)	116 (2)
Aminotetrazolium nitrate	N—H···O	2.7527 (14)	172.7 (18)
	N—H···O	2.7653 (14)	177.2 (18)
Aminotetrazolium perchlorate	N—H···O	2.931 (3)	167 (3)
	N—H···O	2.973 (2)	168 (2)
Aminotetrazolium picrate	N—H···O	3.0105 (13)	152
	N—H···O	2.9999 (13)	169
Aminotetrazole in cocrystal I	N—H···O	2.837 (6)	172 (5)
	N—H···O	3.065 (5)	177 (6)
Aminotetrazole in salt II	N—H···O	2.8643 (19)	163.7 (17)
	N—H···O	2.8643 (19)	167.4 (19)
	N—H···O	2.5668 (17)	178 (2)

pK_a values of acids and base, and ΔpK_a between acids and base top

Acid	pK_a	Product from reaction of AT with acid	ΔpK_a	Compound type
5-Aminotetrazole	6.0
HBr	-9	5-Aminotrerazolium hydrobromide	15	Salt
HCl	-7	Aminotetrazolium chloride	13	Salt
HI	-9.3	Aminotetrazolium iodide	15.3	Salt
NO₃	-1.3	Aminotetrazolium nitrate	7.3	Salt
ClO₄	-10	Aminotetrazolium perchlorate	16	Salt
Picric acid	0.38	Aminotetrazolium picrate	5.68	Form I Salt; Form II Cocrystal
3,5-Dihydroxybenzoic acid	4.04	5-Aminotetrazole–3,5-dihydroxybenzoic acid	1.96	Cocrystal
3,5-Dinitrosalicylic acid	2.02	5-Aminotetrazole–3,5-dinitrosalicylic acid	3.98	Salt

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Structure determination and Hirshfeld surface analysis of new cocrystal and salt forms of 5-amino­tetra­zole with hy­droxy- and nitro-substituted carb­oxy­lic acids

Supporting information

Structure determination and Hirshfeld surface analysis of new cocrystal and salt forms of 5-aminotetrazole with hydroxy- and nitro-substituted carboxylic acids