Supra­molecular inter­actions in salts/cocrystals involving py­rimi­dine derivatives of sulfonate/carb­oxy­lic acid

The crystal structures of three compounds involving amino­py­rimi­dine derivatives are reported, namely, 5-fluoro­cytosinium sul­fan­il­ate–5-fluoro­cytosine–4-aza­niumyl­benzene-1-sulfonate (1/1/1), C₄H₅FN₃O⁺·C₆H₆NO₃S⁻·C₄H₄FN₃O·C₆H₇NO₃S, I, 5-fluoro­cytosine–indole-3-propionic acid (1/1), C₄H₄FN₃O·C₁₁H₁₁NO₂, II, and 2,4,6-tri­amino­py­rimi­dinium 3-nitro­benzoate, C₄H₈N₅⁺·C₇H₄NO₄⁻, III, which have been synthesized and characterized by single-crystal X-ray diffraction. In I, there are two 5-fluoro­cytosine (5FC) mol­ecules (5FC-A and 5FC-B) in the asymmetric unit, with one of the protons disordered between them. 5FC-A and 5FC-B are linked by triple hydro­gen bonds, generating two fused rings [two R₂²(8) ring motifs]. The 5FC-A mol­ecules form a self-complementary base pair [R₂²(8) ring motif] via a pair of N—H...O hydro­gen bonds and the 5FC-B mol­ecules form a similar complementary base pair [R₂²(8) ring motif]. The combination of these two types of pairing generates a supra­molecular ribbon. The 5FC mol­ecules are further hydro­gen bonded to the sul­fan­il­ate anions and sulfanilic acid mol­ecules via N—H...O hydro­gen bonds, generating R₄⁴(22) and R⁶₆(36) ring motifs. In cocrystal II, two types of base pairs (homosynthons) are observed via a pair of N—H...O/N—H...N hydro­gen bonds, generating R₂²(8) ring motifs. The first type of base pair is formed by the inter­action of an N—H group and the carbonyl O atom of 5FC mol­ecules through a couple of N—H...O hydro­gen bonds. Another type of base pair is formed via the amino group and a py­rimi­dine ring N atom of the 5FC mol­ecules through a pair of N—H...N hydro­gen bonds. The base pairs (via N—H...N hydro­gen bonds) are further bridged by the carboxyl OH group of indole-3-propionic acid and the O atom of 5FC through O—H...O hydro­gen bonds on either side of the R₂²(8) motif. This leads to a DDAA array. In salt III, one of the N atoms of the py­rimi­dine ring is protonated and inter­acts with the carboxyl­ate group of the anion through N—H...O hydro­gen bonds, leading to the primary ring motif R₂²(8). Furthermore, the 2,4,6-tri­amino­py­rimi­dinium (TAP) cations form base pairs [R₂²(8) homosynthon] via N—H...N hydro­gen bonds. A carboxyl­ate O atom of the 3-nitrobenzoate anion bridges two of the amino groups on either side of the paired TAP cations to form another ring [R₃²(8)]. This leads to the generation of a quadruple DADA array. The crystal structures are further stabilized by π–π stacking (I and III), C—H...π (I and II), C—F...π (I) and C—O...π (II) inter­actions.

Computing details

Data collection: CrystalClear (Rigaku/MSC, 2008) for (I); APEX3 (Bruker, 2016) for (II); APEX2 (Bruker, 2014) for (III). Cell refinement: CrystalClear (Rigaku/MSC, 2008) for (I); SAINT (Bruker, 2016) for (II); SAINT (Bruker, 2014) for (III). Data reduction: CrystalClear (Rigaku/MSC, 2008) for (I); SAINT (Bruker, 2016) for (II); SAINT (Bruker, 2014) for (III). For all structures, program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a). Program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b) for (I), (II); SHELXL2018 (Sheldrick, 2015b) for (III). For all structures, molecular graphics: PLATON (Spek, 2020), Mercury (Macrae et al., 2020) and POVRay (Cason, 2004); software used to prepare material for publication: PLATON (Spek, 2020) and publCIF (Westrip, 2010).

5-Fluorocytosinium sulfanilate–5-fluorocytosine–4-azaniumylbenzene-1-sulfonate (1/1/1) (I)

Crystal data

C4H5FN3O^+·C6H6NO3S^−·C6H7NO3S·C4H4FN3O	F(000) = 1248
Mr = 604.57	Dx = 1.722 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.4147 (17) Å	Cell parameters from 4633 reflections
b = 5.7191 (7) Å	θ = 2.3–26.6°
c = 27.232 (3) Å	µ = 0.31 mm^−1
β = 103.688 (5)°	T = 200 K
V = 2332.6 (5) Å^3	Prism, colorless
Z = 4	0.38 × 0.26 × 0.10 mm

Data collection

Rigaku AFC8 Mercury CCD diffractometer	3760 reflections with I > 2σ(I)
Radiation source: fine-focused sealed tube	Rint = 0.048
ω scans	θmax = 26.6°, θmin = 2.3°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2008)	h = −18→19
Tmin = 0.887, Tmax = 1.000	k = −7→7
17219 measured reflections	l = −33→34
4632 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: mixed
wR(F^2) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0664P)^2 + 1.1379P] where P = (Fo^2 + 2Fc^2)/3
4632 reflections	(Δ/σ)max < 0.001
412 parameters	Δρmax = 0.53 e Å^−3
3 restraints	Δρmin = −0.53 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	Occ. (<1)
S1B	0.39981 (4)	0.35609 (11)	0.34526 (2)	0.02603 (18)
O3B	0.39286 (13)	0.5410 (3)	0.38077 (7)	0.0346 (5)
O4B	0.32945 (12)	0.3639 (3)	0.29896 (7)	0.0330 (4)
O5B	0.41048 (13)	0.1239 (3)	0.36804 (8)	0.0364 (5)
C7B	0.66464 (16)	0.4805 (4)	0.30380 (9)	0.0234 (5)
C8B	0.61840 (17)	0.2751 (4)	0.28857 (10)	0.0267 (5)
H8B	0.642199	0.159787	0.270324	0.032*
C9B	0.53680 (17)	0.2412 (4)	0.30047 (9)	0.0258 (5)
H9B	0.504496	0.100858	0.290465	0.031*
C10B	0.50151 (16)	0.4109 (4)	0.32700 (9)	0.0231 (5)
C11B	0.54729 (18)	0.6198 (4)	0.34011 (10)	0.0276 (5)
H11B	0.522545	0.738590	0.357039	0.033*
C12B	0.62912 (18)	0.6544 (4)	0.32842 (10)	0.0283 (6)
H12B	0.660645	0.796808	0.337285	0.034*
N5B	0.75216 (15)	0.5137 (4)	0.29307 (9)	0.0262 (5)
S1A	−0.11049 (4)	1.00102 (10)	0.34451 (2)	0.02413 (18)
O3A	−0.10929 (13)	1.2405 (3)	0.36420 (8)	0.0332 (4)
O4A	−0.18064 (12)	0.9736 (3)	0.29809 (7)	0.0304 (4)
O5A	−0.11483 (13)	0.8223 (3)	0.38134 (7)	0.0354 (5)
C7A	0.16026 (17)	0.8754 (4)	0.30938 (9)	0.0241 (5)
C8A	0.09189 (17)	0.7118 (4)	0.29546 (9)	0.0271 (5)
H8A	0.102242	0.570846	0.279306	0.032*
C9A	0.00920 (17)	0.7533 (4)	0.30500 (9)	0.0266 (5)
H9A	−0.036779	0.639763	0.295909	0.032*
C10A	−0.00710 (17)	0.9626 (4)	0.32805 (9)	0.0233 (5)
C11A	0.05967 (17)	1.1291 (4)	0.33979 (10)	0.0264 (5)
H11A	0.048342	1.273408	0.354402	0.032*
C12A	0.14267 (17)	1.0880 (4)	0.33050 (10)	0.0271 (5)
H12A	0.187843	1.204279	0.338461	0.033*
N5A	0.24547 (15)	0.8330 (4)	0.30064 (9)	0.0280 (5)
N1A	0.43160 (15)	0.6281 (4)	0.53699 (9)	0.0290 (5)
H1A	0.487 (2)	0.643 (6)	0.5296 (12)	0.045 (9)*
C2A	0.38321 (17)	0.4348 (4)	0.51809 (9)	0.0261 (5)
O2A	0.41349 (13)	0.2829 (3)	0.49428 (8)	0.0337 (4)
N3A	0.29931 (14)	0.4140 (4)	0.52638 (8)	0.0252 (4)
H3A	0.269 (3)	0.286 (6)	0.515 (2)	0.030*	0.53 (4)
C4A	0.26458 (17)	0.5730 (4)	0.55329 (9)	0.0240 (5)
N4A	0.18516 (16)	0.5435 (4)	0.56177 (9)	0.0314 (5)
H4A1	0.156 (2)	0.411 (6)	0.5513 (12)	0.035 (8)*
H4A2	0.162 (2)	0.643 (6)	0.5809 (13)	0.046 (9)*
C5A	0.31713 (17)	0.7744 (4)	0.57061 (9)	0.0257 (5)
F5A	0.28037 (11)	0.9375 (3)	0.59501 (6)	0.0369 (4)
C6A	0.39835 (18)	0.7995 (4)	0.56241 (10)	0.0285 (5)
H6A	0.432832	0.934829	0.574073	0.034*
N1B	0.06316 (15)	−0.1503 (4)	0.45934 (9)	0.0281 (5)
H1B	0.009 (2)	−0.159 (6)	0.4703 (12)	0.044 (9)*
C2B	0.11622 (17)	0.0348 (4)	0.47817 (9)	0.0243 (5)
O2B	0.08776 (13)	0.1941 (3)	0.50136 (8)	0.0332 (4)
N3B	0.20093 (14)	0.0419 (4)	0.47090 (8)	0.0241 (4)
H3B	0.239 (3)	0.145 (8)	0.486 (2)	0.029*	0.47 (4)
C4B	0.23148 (17)	−0.1262 (4)	0.44445 (9)	0.0237 (5)
N4B	0.31211 (15)	−0.1149 (4)	0.43611 (9)	0.0290 (5)
H4B1	0.342 (2)	0.013 (6)	0.4452 (11)	0.031 (8)*
H4B2	0.332 (2)	−0.225 (6)	0.4171 (13)	0.048 (10)*
C5B	0.17431 (18)	−0.3192 (4)	0.42649 (10)	0.0264 (5)
F5B	0.20706 (11)	−0.4916 (3)	0.40242 (6)	0.0341 (4)
C6B	0.09126 (17)	−0.3281 (4)	0.43382 (10)	0.0275 (5)
H6B	0.052968	−0.455936	0.421446	0.033*
H5B1	0.794 (2)	0.437 (5)	0.3160 (11)	0.029 (7)*
H5B2	0.767 (3)	0.679 (7)	0.2942 (14)	0.060 (11)*
H5B3	0.752 (2)	0.465 (7)	0.2606 (9)	0.063 (12)*
H5A1	0.259 (2)	0.691 (6)	0.3008 (12)	0.040 (9)*
H5A2	0.291 (2)	0.925 (6)	0.3216 (12)	0.039 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1B	0.0214 (3)	0.0264 (3)	0.0320 (4)	0.0010 (2)	0.0096 (3)	0.0028 (2)
O3B	0.0301 (10)	0.0393 (10)	0.0384 (11)	0.0008 (8)	0.0163 (9)	−0.0060 (8)
O4B	0.0218 (9)	0.0375 (10)	0.0380 (11)	0.0013 (8)	0.0036 (8)	0.0015 (8)
O5B	0.0328 (11)	0.0318 (10)	0.0477 (12)	0.0007 (8)	0.0155 (9)	0.0145 (9)
C7B	0.0218 (12)	0.0265 (12)	0.0229 (12)	0.0004 (9)	0.0070 (10)	0.0004 (9)
C8B	0.0250 (13)	0.0265 (12)	0.0293 (13)	−0.0001 (10)	0.0080 (10)	−0.0027 (10)
C9B	0.0252 (13)	0.0211 (11)	0.0307 (13)	−0.0007 (9)	0.0059 (10)	−0.0028 (9)
C10B	0.0190 (12)	0.0265 (12)	0.0243 (12)	0.0010 (9)	0.0060 (9)	0.0021 (9)
C11B	0.0287 (14)	0.0260 (12)	0.0304 (14)	0.0007 (10)	0.0116 (11)	−0.0033 (10)
C12B	0.0278 (13)	0.0267 (12)	0.0309 (14)	−0.0049 (10)	0.0082 (11)	−0.0029 (10)
N5B	0.0220 (11)	0.0263 (11)	0.0313 (12)	−0.0012 (9)	0.0085 (9)	−0.0003 (9)
S1A	0.0221 (3)	0.0239 (3)	0.0278 (4)	−0.0005 (2)	0.0087 (3)	−0.0001 (2)
O3A	0.0297 (10)	0.0280 (9)	0.0449 (11)	−0.0013 (8)	0.0152 (9)	−0.0120 (8)
O4A	0.0239 (9)	0.0346 (10)	0.0310 (10)	−0.0020 (7)	0.0029 (8)	0.0000 (8)
O5A	0.0334 (11)	0.0400 (11)	0.0356 (11)	0.0010 (8)	0.0141 (9)	0.0123 (8)
C7A	0.0233 (13)	0.0285 (12)	0.0214 (12)	0.0033 (10)	0.0070 (10)	0.0024 (9)
C8A	0.0280 (13)	0.0263 (12)	0.0277 (13)	0.0017 (10)	0.0082 (10)	−0.0034 (10)
C9A	0.0263 (13)	0.0234 (12)	0.0295 (13)	−0.0036 (10)	0.0052 (10)	−0.0035 (10)
C10A	0.0244 (12)	0.0251 (12)	0.0215 (12)	0.0009 (9)	0.0074 (10)	0.0001 (9)
C11A	0.0258 (13)	0.0236 (12)	0.0301 (14)	−0.0013 (10)	0.0074 (11)	−0.0037 (10)
C12A	0.0240 (13)	0.0265 (12)	0.0319 (14)	−0.0024 (10)	0.0088 (10)	−0.0036 (10)
N5A	0.0246 (12)	0.0281 (12)	0.0324 (12)	0.0039 (9)	0.0087 (9)	0.0010 (9)
N1A	0.0228 (11)	0.0298 (11)	0.0359 (12)	−0.0045 (9)	0.0097 (10)	−0.0042 (9)
C2A	0.0224 (12)	0.0283 (12)	0.0282 (13)	−0.0005 (10)	0.0076 (10)	−0.0006 (10)
O2A	0.0282 (10)	0.0334 (10)	0.0446 (11)	−0.0033 (8)	0.0185 (9)	−0.0082 (8)
N3A	0.0234 (11)	0.0260 (10)	0.0280 (11)	−0.0020 (8)	0.0095 (9)	−0.0028 (9)
C4A	0.0226 (12)	0.0286 (12)	0.0213 (12)	−0.0002 (10)	0.0059 (10)	0.0013 (9)
N4A	0.0283 (12)	0.0321 (12)	0.0379 (13)	−0.0072 (10)	0.0162 (10)	−0.0100 (10)
C5A	0.0265 (13)	0.0229 (12)	0.0275 (13)	0.0009 (10)	0.0058 (10)	−0.0031 (9)
F5A	0.0360 (9)	0.0346 (8)	0.0428 (9)	−0.0032 (7)	0.0145 (7)	−0.0143 (7)
C6A	0.0270 (13)	0.0252 (12)	0.0324 (14)	−0.0024 (10)	0.0050 (11)	−0.0038 (10)
N1B	0.0229 (11)	0.0295 (11)	0.0345 (12)	−0.0054 (9)	0.0122 (9)	−0.0073 (9)
C2B	0.0249 (12)	0.0282 (12)	0.0215 (12)	0.0013 (10)	0.0085 (10)	−0.0011 (9)
O2B	0.0265 (10)	0.0341 (10)	0.0429 (11)	−0.0033 (8)	0.0157 (9)	−0.0113 (8)
N3B	0.0191 (10)	0.0284 (10)	0.0261 (11)	−0.0029 (8)	0.0079 (8)	−0.0035 (8)
C4B	0.0243 (12)	0.0277 (12)	0.0194 (12)	0.0009 (10)	0.0058 (10)	0.0009 (9)
N4B	0.0259 (12)	0.0316 (12)	0.0314 (12)	−0.0020 (10)	0.0106 (9)	−0.0051 (9)
C5B	0.0298 (13)	0.0234 (12)	0.0266 (13)	0.0020 (10)	0.0080 (10)	−0.0030 (9)
F5B	0.0332 (9)	0.0304 (8)	0.0410 (9)	0.0010 (6)	0.0132 (7)	−0.0102 (6)
C6B	0.0269 (13)	0.0245 (12)	0.0315 (14)	−0.0041 (10)	0.0076 (11)	−0.0044 (10)

Geometric parameters (Å, º)

S1B—O3B	1.4540 (19)	C12A—H12A	0.9500
S1B—O4B	1.456 (2)	N5A—H5A1	0.84 (4)
S1B—O5B	1.4586 (19)	N5A—H5A2	0.95 (4)
S1B—C10B	1.781 (2)	N1A—C2A	1.364 (3)
C7B—C12B	1.383 (3)	N1A—C6A	1.368 (3)
C7B—C8B	1.386 (3)	N1A—H1A	0.92 (4)
C7B—N5B	1.459 (3)	C2A—O2A	1.240 (3)
C8B—C9B	1.385 (3)	C2A—N3A	1.370 (3)
C8B—H8B	0.9500	N3A—C4A	1.355 (3)
C9B—C10B	1.395 (3)	N3A—H3A	0.88 (2)
C9B—H9B	0.9500	C4A—N4A	1.309 (3)
C10B—C11B	1.390 (4)	C4A—C5A	1.423 (4)
C11B—C12B	1.386 (4)	N4A—H4A1	0.90 (3)
C11B—H11B	0.9500	N4A—H4A2	0.90 (4)
C12B—H12B	0.9500	C5A—C6A	1.331 (4)
N5B—H5B1	0.90 (3)	C5A—F5A	1.346 (3)
N5B—H5B2	0.97 (4)	C6A—H6A	0.9500
N5B—H5B3	0.926 (19)	N1B—C6B	1.359 (3)
S1A—O5A	1.4443 (19)	N1B—C2B	1.362 (3)
S1A—O4A	1.465 (2)	N1B—H1B	0.95 (4)
S1A—O3A	1.4695 (18)	C2B—O2B	1.246 (3)
S1A—C10A	1.768 (2)	C2B—N3B	1.367 (3)
C7A—C8A	1.393 (4)	N3B—C4B	1.351 (3)
C7A—C12A	1.399 (3)	N3B—H3B	0.87 (2)
C7A—N5A	1.410 (3)	C4B—N4B	1.317 (3)
C8A—C9A	1.380 (4)	C4B—C5B	1.425 (4)
C8A—H8A	0.9500	N4B—H4B1	0.87 (3)
C9A—C10A	1.401 (3)	N4B—H4B2	0.91 (4)
C9A—H9A	0.9500	C5B—C6B	1.342 (4)
C10A—C11A	1.383 (4)	C5B—F5B	1.347 (3)
C11A—C12A	1.382 (4)	C6B—H6B	0.9500
C11A—H11A	0.9500
O3B—S1B—O4B	113.37 (12)	C10A—C11A—H11A	119.6
O3B—S1B—O5B	113.46 (12)	C11A—C12A—C7A	120.1 (2)
O4B—S1B—O5B	112.46 (12)	C11A—C12A—H12A	120.0
O3B—S1B—C10B	105.42 (11)	C7A—C12A—H12A	120.0
O4B—S1B—C10B	106.09 (11)	C7A—N5A—H5A1	114 (2)
O5B—S1B—C10B	105.13 (11)	C7A—N5A—H5A2	112.8 (19)
C12B—C7B—C8B	121.3 (2)	H5A1—N5A—H5A2	112 (3)
C12B—C7B—N5B	119.7 (2)	C2A—N1A—C6A	122.3 (2)
C8B—C7B—N5B	119.0 (2)	C2A—N1A—H1A	116 (2)
C9B—C8B—C7B	118.7 (2)	C6A—N1A—H1A	121 (2)
C9B—C8B—H8B	120.7	O2A—C2A—N1A	121.7 (2)
C7B—C8B—H8B	120.7	O2A—C2A—N3A	120.8 (2)
C8B—C9B—C10B	120.7 (2)	N1A—C2A—N3A	117.5 (2)
C8B—C9B—H9B	119.6	C4A—N3A—C2A	122.7 (2)
C10B—C9B—H9B	119.6	C4A—N3A—H3A	120 (4)
C11B—C10B—C9B	119.6 (2)	C2A—N3A—H3A	117 (4)
C11B—C10B—S1B	120.42 (19)	N4A—C4A—N3A	121.0 (2)
C9B—C10B—S1B	119.93 (19)	N4A—C4A—C5A	121.9 (2)
C12B—C11B—C10B	119.8 (2)	N3A—C4A—C5A	117.1 (2)
C12B—C11B—H11B	120.1	C4A—N4A—H4A1	119 (2)
C10B—C11B—H11B	120.1	C4A—N4A—H4A2	122 (2)
C7B—C12B—C11B	119.7 (2)	H4A1—N4A—H4A2	118 (3)
C7B—C12B—H12B	120.2	C6A—C5A—F5A	122.1 (2)
C11B—C12B—H12B	120.2	C6A—C5A—C4A	121.1 (2)
C7B—N5B—H5B1	110.0 (19)	F5A—C5A—C4A	116.9 (2)
C7B—N5B—H5B2	110 (2)	C5A—C6A—N1A	119.2 (2)
H5B1—N5B—H5B2	109 (3)	C5A—C6A—H6A	120.4
C7B—N5B—H5B3	111 (2)	N1A—C6A—H6A	120.4
H5B1—N5B—H5B3	111 (3)	C6B—N1B—C2B	122.6 (2)
H5B2—N5B—H5B3	106 (3)	C6B—N1B—H1B	122 (2)
O5A—S1A—O4A	112.18 (12)	C2B—N1B—H1B	115 (2)
O5A—S1A—O3A	113.88 (12)	O2B—C2B—N1B	120.5 (2)
O4A—S1A—O3A	110.96 (12)	O2B—C2B—N3B	121.0 (2)
O5A—S1A—C10A	106.30 (11)	N1B—C2B—N3B	118.5 (2)
O4A—S1A—C10A	107.06 (11)	C4B—N3B—C2B	121.4 (2)
O3A—S1A—C10A	105.91 (11)	C4B—N3B—H3B	117 (4)
C8A—C7A—C12A	119.2 (2)	C2B—N3B—H3B	121 (4)
C8A—C7A—N5A	120.9 (2)	N4B—C4B—N3B	121.3 (2)
C12A—C7A—N5A	119.9 (2)	N4B—C4B—C5B	120.7 (2)
C9A—C8A—C7A	120.4 (2)	N3B—C4B—C5B	118.0 (2)
C9A—C8A—H8A	119.8	C4B—N4B—H4B1	117 (2)
C7A—C8A—H8A	119.8	C4B—N4B—H4B2	121 (2)
C8A—C9A—C10A	120.2 (2)	H4B1—N4B—H4B2	121 (3)
C8A—C9A—H9A	119.9	C6B—C5B—F5B	121.7 (2)
C10A—C9A—H9A	119.9	C6B—C5B—C4B	120.8 (2)
C11A—C10A—C9A	119.3 (2)	F5B—C5B—C4B	117.5 (2)
C11A—C10A—S1A	121.45 (19)	C5B—C6B—N1B	118.6 (2)
C9A—C10A—S1A	119.18 (19)	C5B—C6B—H6B	120.7
C12A—C11A—C10A	120.7 (2)	N1B—C6B—H6B	120.7
C12A—C11A—H11A	119.6

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O2A^i	0.92 (4)	1.86 (4)	2.766 (3)	169 (3)
N3A—H3A···N3B	0.88 (2)	1.98 (3)	2.833 (3)	163 (5)
N4A—H4A1···O5A^ii	0.90 (3)	2.47 (3)	2.958 (3)	115 (2)
N4A—H4A1···O2B	0.90 (3)	1.95 (3)	2.790 (3)	155 (3)
N4A—H4A2···O3A^iii	0.90 (4)	1.98 (4)	2.841 (3)	160 (3)
C6A—H6A···O5B^i	0.95	2.57	3.134 (3)	118
N1B—H1B···O2B^iv	0.95 (4)	1.85 (4)	2.792 (3)	173 (3)
N3B—H3B···N3A	0.87 (2)	1.99 (3)	2.833 (3)	165 (6)
N4B—H4B1···O2A	0.87 (3)	2.16 (3)	2.993 (3)	159 (3)
N4B—H4B2···O3B^v	0.91 (4)	2.02 (4)	2.929 (3)	172 (3)
N5B—H5B1···O3A^vi	0.90 (3)	2.07 (3)	2.966 (3)	175 (3)
N5B—H5B2···O4A^vii	0.97 (4)	1.86 (4)	2.818 (3)	168 (3)
N5B—H5B3···N5A^viii	0.93 (2)	1.84 (2)	2.761 (3)	173 (4)
N5A—H5A1···O4B	0.84 (4)	2.17 (4)	2.984 (3)	164 (3)
N5A—H5A2···O5B^ix	0.95 (4)	2.28 (4)	3.224 (3)	174 (3)

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

5-Fluorocytosine–indole-3-propionic acid (1/1) (II)

Crystal data

C4H4FN3O·C11H11NO2	F(000) = 664
Mr = 318.31	Dx = 1.456 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.0919 (5) Å	Cell parameters from 4429 reflections
b = 5.2273 (3) Å	θ = 2.3–30.5°
c = 30.5813 (18) Å	µ = 0.11 mm^−1
β = 92.042 (2)°	T = 100 K
V = 1452.49 (14) Å^3	Prism, colorless
Z = 4	0.57 × 0.41 × 0.07 mm

Data collection

Bruker D8 Venture Photon 100 diffractometer	2672 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.044
φ and ω scans	θmax = 26.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −11→11
Tmin = 0.908, Tmax = 1.000	k = −6→6
27046 measured reflections	l = −38→38
3015 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: mixed
wR(F^2) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0374P)^2 + 1.0091P] where P = (Fo^2 + 2Fc^2)/3
3015 reflections	(Δ/σ)max = 0.001
228 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.26 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
F5	0.99368 (9)	−0.14131 (16)	0.40926 (3)	0.0190 (2)
O2	0.61070 (11)	0.2532 (2)	0.51890 (3)	0.0195 (2)
O3	0.64944 (12)	0.6587 (2)	0.56804 (4)	0.0307 (3)
H3	0.632 (3)	0.522 (5)	0.5510 (8)	0.062 (8)*
O4	0.43144 (12)	0.5841 (2)	0.59607 (4)	0.0267 (3)
N1	0.66954 (13)	−0.0537 (2)	0.47053 (4)	0.0150 (3)
H1	0.581 (2)	−0.126 (4)	0.4749 (6)	0.032 (5)*
N3	0.83630 (12)	0.2777 (2)	0.48894 (4)	0.0135 (2)
N4	1.05972 (13)	0.2916 (3)	0.45585 (4)	0.0169 (3)
H4A	1.087 (2)	0.431 (4)	0.4729 (6)	0.033 (5)*
H4B	1.122 (2)	0.230 (4)	0.4385 (6)	0.023 (5)*
N7	0.64109 (14)	1.4323 (3)	0.73943 (4)	0.0182 (3)
H7	0.690 (2)	1.569 (4)	0.7442 (6)	0.032 (5)*
C5	0.89381 (15)	−0.0469 (3)	0.43677 (4)	0.0138 (3)
C6	0.76363 (15)	−0.1600 (3)	0.44189 (4)	0.0146 (3)
H6	0.737364	−0.310366	0.426010	0.017*
C4	0.93094 (15)	0.1788 (3)	0.46085 (4)	0.0132 (3)
C18	0.54465 (15)	0.7031 (3)	0.59592 (4)	0.0161 (3)
C9	0.52960 (15)	1.1191 (3)	0.69988 (4)	0.0148 (3)
C2	0.70412 (15)	0.1643 (3)	0.49362 (4)	0.0141 (3)
C15	0.47940 (15)	1.1090 (3)	0.74396 (4)	0.0151 (3)
C17	0.58444 (16)	0.9173 (3)	0.62711 (5)	0.0181 (3)
H17A	0.585964	1.080408	0.610676	0.022*
H17B	0.684707	0.887190	0.639744	0.022*
C16	0.47806 (15)	0.9416 (3)	0.66397 (5)	0.0177 (3)
H16A	0.382310	1.003665	0.651723	0.021*
H16B	0.461848	0.769952	0.676597	0.021*
C8	0.62694 (16)	1.3174 (3)	0.69865 (5)	0.0173 (3)
H8	0.677637	1.369254	0.673504	0.021*
C14	0.54889 (15)	1.3096 (3)	0.76747 (5)	0.0160 (3)
C13	0.52130 (16)	1.3566 (3)	0.81147 (5)	0.0200 (3)
H13	0.567525	1.493847	0.826985	0.024*
C10	0.38174 (16)	0.9468 (3)	0.76515 (5)	0.0190 (3)
H10	0.334692	0.809478	0.749864	0.023*
C11	0.35541 (18)	0.9911 (3)	0.80876 (5)	0.0233 (3)
H11	0.290024	0.882277	0.823606	0.028*
C12	0.42401 (17)	1.1948 (3)	0.83137 (5)	0.0233 (3)
H12	0.402907	1.222065	0.861217	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F5	0.0199 (4)	0.0196 (4)	0.0179 (4)	−0.0017 (3)	0.0076 (3)	−0.0054 (3)
O2	0.0157 (5)	0.0202 (6)	0.0230 (5)	−0.0047 (4)	0.0065 (4)	−0.0101 (4)
O3	0.0223 (6)	0.0340 (7)	0.0369 (7)	−0.0134 (5)	0.0144 (5)	−0.0239 (6)
O4	0.0224 (6)	0.0320 (7)	0.0262 (6)	−0.0128 (5)	0.0079 (5)	−0.0140 (5)
N1	0.0131 (6)	0.0149 (6)	0.0172 (6)	−0.0049 (5)	0.0030 (5)	−0.0037 (5)
N3	0.0137 (6)	0.0135 (6)	0.0132 (5)	−0.0025 (5)	0.0011 (4)	−0.0017 (5)
N4	0.0154 (6)	0.0179 (6)	0.0178 (6)	−0.0050 (5)	0.0051 (5)	−0.0053 (5)
N7	0.0203 (6)	0.0151 (6)	0.0192 (6)	−0.0032 (5)	0.0001 (5)	−0.0041 (5)
C5	0.0170 (7)	0.0143 (7)	0.0102 (6)	0.0005 (5)	0.0029 (5)	−0.0012 (5)
C6	0.0183 (7)	0.0128 (7)	0.0126 (6)	−0.0013 (6)	−0.0001 (5)	−0.0023 (5)
C4	0.0149 (6)	0.0140 (7)	0.0108 (6)	−0.0014 (5)	−0.0004 (5)	0.0023 (5)
C18	0.0164 (7)	0.0171 (7)	0.0149 (6)	−0.0013 (6)	0.0013 (5)	−0.0021 (6)
C9	0.0138 (6)	0.0145 (7)	0.0161 (7)	0.0034 (5)	−0.0004 (5)	−0.0016 (5)
C2	0.0144 (7)	0.0145 (7)	0.0134 (6)	−0.0012 (5)	0.0004 (5)	−0.0012 (5)
C15	0.0141 (6)	0.0140 (7)	0.0171 (7)	0.0045 (5)	−0.0013 (5)	−0.0022 (5)
C17	0.0184 (7)	0.0175 (7)	0.0185 (7)	−0.0051 (6)	0.0023 (6)	−0.0051 (6)
C16	0.0164 (7)	0.0191 (7)	0.0175 (7)	−0.0011 (6)	0.0005 (5)	−0.0044 (6)
C8	0.0195 (7)	0.0166 (7)	0.0158 (7)	0.0006 (6)	0.0010 (5)	−0.0012 (6)
C14	0.0147 (6)	0.0147 (7)	0.0183 (7)	0.0036 (6)	−0.0011 (5)	−0.0012 (6)
C13	0.0212 (7)	0.0209 (8)	0.0177 (7)	0.0039 (6)	−0.0027 (6)	−0.0062 (6)
C10	0.0188 (7)	0.0164 (7)	0.0217 (7)	0.0006 (6)	0.0012 (6)	−0.0021 (6)
C11	0.0252 (8)	0.0225 (8)	0.0225 (8)	0.0009 (6)	0.0062 (6)	0.0029 (6)
C12	0.0281 (8)	0.0268 (8)	0.0152 (7)	0.0071 (7)	0.0020 (6)	−0.0017 (6)

Geometric parameters (Å, º)

F5—C5	1.3529 (15)	C9—C8	1.365 (2)
O2—C2	1.2578 (17)	C9—C15	1.4393 (19)
O3—C18	1.3214 (17)	C9—C16	1.500 (2)
O3—H3	0.89 (3)	C15—C10	1.403 (2)
O4—C18	1.2029 (18)	C15—C14	1.409 (2)
N1—C6	1.3642 (18)	C17—C16	1.5165 (19)
N1—C2	1.3712 (18)	C17—H17A	0.9900
N1—H1	0.90 (2)	C17—H17B	0.9900
N3—C4	1.3411 (17)	C16—H16A	0.9900
N3—C2	1.3522 (18)	C16—H16B	0.9900
N4—C4	1.3244 (18)	C8—H8	0.9500
N4—H4A	0.93 (2)	C14—C13	1.399 (2)
N4—H4B	0.852 (19)	C13—C12	1.381 (2)
N7—C14	1.3785 (19)	C13—H13	0.9500
N7—C8	1.3859 (19)	C10—C11	1.383 (2)
N7—H7	0.85 (2)	C10—H10	0.9500
C5—C6	1.337 (2)	C11—C12	1.403 (2)
C5—C4	1.425 (2)	C11—H11	0.9500
C6—H6	0.9500	C12—H12	0.9500
C18—C17	1.506 (2)
C18—O3—H3	113.7 (16)	C14—C15—C9	107.42 (13)
C6—N1—C2	122.11 (12)	C18—C17—C16	112.82 (12)
C6—N1—H1	120.5 (13)	C18—C17—H17A	109.0
C2—N1—H1	117.3 (13)	C16—C17—H17A	109.0
C4—N3—C2	119.45 (12)	C18—C17—H17B	109.0
C4—N4—H4A	120.5 (12)	C16—C17—H17B	109.0
C4—N4—H4B	121.0 (13)	H17A—C17—H17B	107.8
H4A—N4—H4B	118.3 (17)	C9—C16—C17	113.90 (12)
C14—N7—C8	108.61 (13)	C9—C16—H16A	108.8
C14—N7—H7	127.7 (13)	C17—C16—H16A	108.8
C8—N7—H7	123.1 (13)	C9—C16—H16B	108.8
C6—C5—F5	121.88 (13)	C17—C16—H16B	108.8
C6—C5—C4	120.00 (12)	H16A—C16—H16B	107.7
F5—C5—C4	118.12 (12)	C9—C8—N7	110.12 (13)
C5—C6—N1	118.23 (13)	C9—C8—H8	124.9
C5—C6—H6	120.9	N7—C8—H8	124.9
N1—C6—H6	120.9	N7—C14—C13	130.58 (14)
N4—C4—N3	119.50 (13)	N7—C14—C15	107.49 (12)
N4—C4—C5	120.20 (12)	C13—C14—C15	121.93 (14)
N3—C4—C5	120.30 (12)	C12—C13—C14	117.14 (14)
O4—C18—O3	123.26 (13)	C12—C13—H13	121.4
O4—C18—C17	124.62 (13)	C14—C13—H13	121.4
O3—C18—C17	112.13 (12)	C11—C10—C15	118.59 (14)
C8—C9—C15	106.33 (12)	C11—C10—H10	120.7
C8—C9—C16	129.48 (13)	C15—C10—H10	120.7
C15—C9—C16	124.18 (13)	C10—C11—C12	120.87 (15)
O2—C2—N3	121.69 (13)	C10—C11—H11	119.6
O2—C2—N1	118.43 (12)	C12—C11—H11	119.6
N3—C2—N1	119.89 (12)	C13—C12—C11	121.85 (14)
C10—C15—C14	119.60 (13)	C13—C12—H12	119.1
C10—C15—C9	132.98 (14)	C11—C12—H12	119.1

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.89 (3)	1.72 (3)	2.6150 (15)	177 (2)
N1—H1···O2^i	0.90 (2)	1.89 (2)	2.7825 (16)	175.0 (19)
N4—H4A···N3^ii	0.93 (2)	2.03 (2)	2.9494 (17)	175.2 (18)
N4—H4B···O3^ii	0.852 (19)	2.174 (18)	2.7805 (16)	128.0 (16)
N7—H7···N7^iii	0.85 (2)	2.48 (2)	3.3287 (16)	173.1 (18)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+2, −y+1, −z+1; (iii) −x+3/2, y+1/2, −z+3/2.

2,4,6-Triaminopyrimidinium 3-nitrobenzoate (III)

Crystal data

C4H8N5^+·C7H4NO4^−	F(000) = 1216
Mr = 292.27	Dx = 1.366 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.581 (3) Å	Cell parameters from 9966 reflections
b = 10.3368 (16) Å	θ = 2.5–40.3°
c = 13.853 (2) Å	µ = 0.11 mm^−1
β = 113.155 (5)°	T = 120 K
V = 2841.4 (8) Å^3	Block, colourless
Z = 8	0.21 × 0.19 × 0.18 mm

Data collection

Bruker APEXII diffractometer	6174 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.045
ω scans	θmax = 40.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −39→39
Tmin = 0.676, Tmax = 0.748	k = −18→18
37277 measured reflections	l = −23→25
8912 independent reflections

Refinement

Refinement on F^2	12 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.144	w = 1/[σ^2(Fo^2) + (0.0703P)^2 + 0.8862P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
8912 reflections	Δρmax = 0.67 e Å^−3
222 parameters	Δρmin = −0.31 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	Occ. (<1)
O1A	0.31627 (3)	0.36179 (6)	0.58374 (5)	0.01634 (11)
O2A	0.41678 (3)	0.26497 (5)	0.65422 (5)	0.01308 (10)
O3A	0.61524 (3)	0.49887 (7)	0.66858 (6)	0.02610 (15)
O4AA	0.60950 (11)	0.6997 (3)	0.6228 (6)	0.0315 (7)	0.80 (2)
O4AB	0.6118 (5)	0.7093 (10)	0.6519 (14)	0.0315 (7)	0.20 (2)
N6	0.58393 (4)	0.60008 (7)	0.64023 (6)	0.01970 (14)
C7	0.41312 (4)	0.48585 (6)	0.60468 (6)	0.01235 (12)
C8	0.48145 (4)	0.48567 (7)	0.62534 (6)	0.01262 (12)
H8A	0.506771	0.407719	0.643099	0.015*
C9	0.51202 (4)	0.60189 (7)	0.61948 (6)	0.01567 (13)
C10	0.47763 (5)	0.71879 (8)	0.59618 (8)	0.02350 (18)
H10A	0.500072	0.796958	0.593583	0.028*
C11	0.40945 (5)	0.71796 (8)	0.57679 (9)	0.0280 (2)
H11A	0.384725	0.796657	0.561689	0.034*
C12	0.37710 (4)	0.60197 (8)	0.57940 (8)	0.02084 (16)
H12A	0.330126	0.601901	0.563840	0.025*
C13	0.37893 (4)	0.36201 (6)	0.61412 (6)	0.01140 (11)
N1	0.37011 (3)	0.13605 (6)	0.78266 (5)	0.01373 (11)
N3	0.40595 (3)	0.00773 (6)	0.93608 (5)	0.01252 (11)
N2	0.48289 (3)	0.10099 (7)	0.87938 (6)	0.01684 (13)
N5	0.25936 (4)	0.17413 (8)	0.67659 (7)	0.02211 (15)
N4	0.32747 (4)	−0.07849 (7)	0.99144 (6)	0.01575 (12)
C2	0.41908 (4)	0.08044 (6)	0.86720 (6)	0.01214 (12)
C6	0.30345 (4)	0.11802 (7)	0.76297 (6)	0.01438 (13)
C5	0.28689 (4)	0.04301 (7)	0.83229 (6)	0.01510 (13)
H5B	0.241218	0.027932	0.821550	0.018*
C4	0.33982 (4)	−0.00974 (6)	0.91869 (6)	0.01202 (12)
H1B	0.3821 (7)	0.1791 (13)	0.7366 (11)	0.025 (3)*
H2B1	0.4930 (7)	0.1544 (12)	0.8423 (11)	0.021 (3)*
H2B2	0.5141 (7)	0.0704 (13)	0.9325 (11)	0.023 (3)*
H5B1	0.2166 (8)	0.1687 (14)	0.6588 (11)	0.029 (4)*
H5B2	0.2743 (8)	0.2294 (16)	0.6450 (12)	0.038 (4)*
H4B2	0.3611 (7)	−0.1235 (13)	1.0382 (11)	0.023 (3)*
H4B1	0.2860 (7)	−0.0901 (13)	0.9792 (10)	0.023 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0079 (2)	0.0187 (2)	0.0213 (3)	0.00035 (17)	0.0046 (2)	0.00280 (19)
O2A	0.0099 (2)	0.01261 (19)	0.0168 (3)	0.00151 (15)	0.0054 (2)	0.00195 (17)
O3A	0.0128 (3)	0.0291 (3)	0.0350 (4)	0.0017 (2)	0.0080 (3)	0.0087 (3)
O4AA	0.0206 (4)	0.0288 (5)	0.0478 (19)	−0.0085 (3)	0.0162 (8)	0.0090 (8)
O4AB	0.0206 (4)	0.0288 (5)	0.0478 (19)	−0.0085 (3)	0.0162 (8)	0.0090 (8)
N6	0.0123 (3)	0.0240 (3)	0.0222 (3)	−0.0039 (2)	0.0062 (3)	0.0046 (2)
C7	0.0092 (3)	0.0135 (2)	0.0140 (3)	0.00068 (19)	0.0041 (2)	0.0031 (2)
C8	0.0099 (3)	0.0144 (2)	0.0132 (3)	−0.0001 (2)	0.0042 (2)	0.0020 (2)
C9	0.0114 (3)	0.0174 (3)	0.0179 (3)	−0.0020 (2)	0.0055 (3)	0.0039 (2)
C10	0.0203 (4)	0.0164 (3)	0.0344 (5)	−0.0009 (3)	0.0114 (4)	0.0092 (3)
C11	0.0219 (4)	0.0164 (3)	0.0476 (6)	0.0047 (3)	0.0157 (4)	0.0130 (3)
C12	0.0139 (3)	0.0171 (3)	0.0324 (5)	0.0042 (2)	0.0100 (3)	0.0096 (3)
C13	0.0089 (3)	0.0130 (2)	0.0125 (3)	−0.00002 (19)	0.0043 (2)	0.0004 (2)
N1	0.0091 (3)	0.0172 (2)	0.0145 (3)	0.00043 (19)	0.0042 (2)	0.0050 (2)
N3	0.0079 (2)	0.0145 (2)	0.0142 (3)	−0.00131 (17)	0.0033 (2)	0.00266 (19)
N2	0.0082 (3)	0.0230 (3)	0.0185 (3)	−0.0008 (2)	0.0044 (2)	0.0077 (2)
N5	0.0101 (3)	0.0318 (4)	0.0214 (4)	0.0016 (2)	0.0029 (3)	0.0136 (3)
N4	0.0091 (3)	0.0202 (3)	0.0172 (3)	−0.0014 (2)	0.0043 (2)	0.0066 (2)
C2	0.0086 (3)	0.0132 (2)	0.0139 (3)	−0.00043 (19)	0.0036 (2)	0.0012 (2)
C6	0.0092 (3)	0.0175 (3)	0.0151 (3)	0.0002 (2)	0.0033 (2)	0.0031 (2)
C5	0.0079 (3)	0.0189 (3)	0.0171 (3)	−0.0006 (2)	0.0035 (3)	0.0047 (2)
C4	0.0091 (3)	0.0122 (2)	0.0141 (3)	−0.00125 (19)	0.0038 (2)	0.0009 (2)

Geometric parameters (Å, º)

O1A—C13	1.2482 (9)	N1—C2	1.3585 (10)
O2A—C13	1.2748 (9)	N1—C6	1.3676 (10)
O3A—N6	1.2232 (10)	N1—H1B	0.895 (14)
O4AA—N6	1.236 (2)	N3—C2	1.3298 (9)
O4AB—N6	1.259 (10)	N3—C4	1.3628 (10)
N6—C9	1.4632 (11)	N2—C2	1.3369 (10)
C7—C8	1.3874 (11)	N2—H2B1	0.840 (14)
C7—C12	1.3977 (10)	N2—H2B2	0.840 (14)
C7—C13	1.5088 (10)	N5—C6	1.3335 (11)
C8—C9	1.3882 (10)	N5—H5B1	0.859 (15)
C8—H8A	0.9500	N5—H5B2	0.856 (16)
C9—C10	1.3881 (12)	N4—C4	1.3427 (10)
C10—C11	1.3880 (14)	N4—H4B2	0.891 (14)
C10—H10A	0.9500	N4—H4B1	0.851 (14)
C11—C12	1.3950 (12)	C6—C5	1.3861 (11)
C11—H11A	0.9500	C5—C4	1.3999 (11)
C12—H12A	0.9500	C5—H5B	0.9500
O3A—N6—O4AA	122.86 (13)	C2—N1—C6	121.00 (6)
O3A—N6—O4AB	123.4 (5)	C2—N1—H1B	118.7 (9)
O3A—N6—C9	118.90 (7)	C6—N1—H1B	120.1 (9)
O4AA—N6—C9	118.12 (12)	C2—N3—C4	116.87 (6)
O4AB—N6—C9	115.4 (5)	C2—N2—H2B1	122.0 (9)
C8—C7—C12	119.61 (7)	C2—N2—H2B2	118.9 (10)
C8—C7—C13	119.83 (6)	H2B1—N2—H2B2	118.2 (13)
C12—C7—C13	120.50 (7)	C6—N5—H5B1	122.4 (10)
C7—C8—C9	118.54 (7)	C6—N5—H5B2	118.0 (10)
C7—C8—H8A	120.7	H5B1—N5—H5B2	118.4 (14)
C9—C8—H8A	120.7	C4—N4—H4B2	118.4 (9)
C10—C9—C8	122.96 (8)	C4—N4—H4B1	115.4 (9)
C10—C9—N6	119.06 (7)	H4B2—N4—H4B1	124.3 (13)
C8—C9—N6	117.98 (7)	N3—C2—N2	119.92 (7)
C11—C10—C9	117.96 (7)	N3—C2—N1	123.01 (7)
C11—C10—H10A	121.0	N2—C2—N1	117.07 (7)
C9—C10—H10A	121.0	N5—C6—N1	116.31 (7)
C10—C11—C12	120.23 (8)	N5—C6—C5	125.28 (8)
C10—C11—H11A	119.9	N1—C6—C5	118.41 (7)
C12—C11—H11A	119.9	C6—C5—C4	117.66 (7)
C11—C12—C7	120.66 (8)	C6—C5—H5B	121.2
C11—C12—H12A	119.7	C4—C5—H5B	121.2
C7—C12—H12A	119.7	N4—C4—N3	116.14 (7)
O1A—C13—O2A	124.69 (6)	N4—C4—C5	120.79 (7)
O1A—C13—C7	118.31 (6)	N3—C4—C5	123.04 (7)
O2A—C13—C7	116.99 (6)
C12—C7—C8—C9	−0.42 (12)	C8—C7—C13—O1A	−172.02 (7)
C13—C7—C8—C9	−177.84 (7)	C12—C7—C13—O1A	10.58 (11)
C7—C8—C9—C10	1.48 (13)	C8—C7—C13—O2A	8.85 (11)
C7—C8—C9—N6	−179.29 (7)	C12—C7—C13—O2A	−168.55 (8)
O3A—N6—C9—C10	174.46 (9)	C4—N3—C2—N2	−179.70 (7)
O4AA—N6—C9—C10	−9.3 (4)	C4—N3—C2—N1	−0.02 (11)
O4AB—N6—C9—C10	11.0 (9)	C6—N1—C2—N3	−1.00 (11)
O3A—N6—C9—C8	−4.79 (12)	C6—N1—C2—N2	178.70 (7)
O4AA—N6—C9—C8	171.4 (4)	C2—N1—C6—N5	−178.38 (8)
O4AB—N6—C9—C8	−168.2 (9)	C2—N1—C6—C5	0.93 (11)
C8—C9—C10—C11	−0.79 (15)	N5—C6—C5—C4	179.32 (8)
N6—C9—C10—C11	180.00 (9)	N1—C6—C5—C4	0.07 (11)
C9—C10—C11—C12	−0.96 (16)	C2—N3—C4—N4	−177.10 (7)
C10—C11—C12—C7	2.00 (16)	C2—N3—C4—C5	1.08 (11)
C8—C7—C12—C11	−1.28 (14)	C6—C5—C4—N4	176.99 (7)
C13—C7—C12—C11	176.12 (9)	C6—C5—C4—N3	−1.11 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2A	0.895 (14)	1.823 (15)	2.7139 (9)	173.2 (13)
N2—H2B1···O2A^i	0.840 (14)	2.242 (14)	2.9276 (9)	139.0 (12)
N2—H2B2···N3^ii	0.840 (14)	2.115 (14)	2.9548 (10)	178.7 (14)
N5—H5B1···O4AA^iii	0.859 (15)	2.188 (16)	3.032 (2)	167.4 (13)
N5—H5B1···O4AB^iii	0.859 (15)	2.265 (19)	3.089 (11)	160.6 (14)
N5—H5B2···O1A	0.856 (16)	2.005 (17)	2.8579 (10)	174.8 (15)
N4—H4B2···O2A^iv	0.891 (14)	2.156 (14)	3.0162 (9)	162.2 (13)
N4—H4B1···O1A^v	0.851 (14)	2.090 (14)	2.9237 (10)	166.4 (13)

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1, −y, −z+2; (iii) x−1/2, y−1/2, z; (iv) x, −y, z+1/2; (v) −x+1/2, y−1/2, −z+3/2.