Cation tautomerism, twinning and disorder in the triclinic and monoclinic forms of 4-amino-5-chloro-2,6-di­methyl­pyrimidinium 5-chloro-2-hy­droxy­benzoate and a new disordered refinement of 2-amino-4,6-di­meth­oxy­pyrimidin-1-ium thio­phene-2-carboxyl­ate

Pyrimidines are important compounds in biology and medicine, and the amino­pyrimidine fragment can be identified in three of the four bases in DNA. The targeted drug action of pharmaceuticals containing this functionality is likely to depend heavily on mol­ecular recognition processes involving hydrogen bonding. Crystallization of an equimolar mixture of 4-amino-5-chloro-2,6-di­methyl­pyrimidine and 5-chloro-2-hy­droxy­benzoic acid yielded two forms of the 1:1 salt, C₆H₉ClN₃⁺·C₇H₄ClO₃⁻, each containing a different tautomeric form of the cation. 6-Amino-5-chloro-2,4-di­methyl­pyrimidin-1-ium 5-chloro-2-hy­droxy­benzoate, (I), crystallizes in the space group P, with Z′ = 2, and all of the component ions are fully ordered. 4-Amino-5-chloro-2,6-di­methyl­pyrimidin-1-ium 5-chloro-2-hy­droxy­benzoate, (II), also crystallizes with Z′ = 2, but in the space group P2₁/c and as a merohedral twin which closely mimics an ortho­rhom­bic unit cell. In (II), one of the cations and one of the anions is disordered, each over two sets of atomic sites having occupancies of 0.836 (2) and 0.164 (2), and 0.834 (2) and 0.166 (2). The bond lengths in the cations of (I) and (II) provide evidence for o-quinonoid and p-quinonoid bond fixation, respectively. A combination of six N—H...O hydrogen bonds links the component ions of (I) into two independent four-ion aggregates, but the ions in (II) are linked by a combination of four N—H...O and two N—H...N hydrogen bonds to form a three-dimensional framework structure. The recently reported structure of 2-amino-4,6-di­meth­oxy­pyrimidin-1-ium thio­phene-2-carboxyl­ate, C₆H₁₀N₃O₂⁺·C₅H₃O₂S⁻, (III), has been rerefined, using the original data set, to show that the anion is disordered over two sets of atomic sites, approximately related by a 180° rotation about the exocyclic C—C bond, and having occupancies of 0.8687 (19) and 0.1313 (19).

Computing details

Data collection: APEX2 (Bruker, 2013) for (I), (II); CrysAlis PRO (Agilent, 2012) for (III). Cell refinement: APEX2 and SAINT (Bruker, 2013) for (I), (II); CrysAlis PRO (Agilent, 2012) for (III). Data reduction: SAINT (Bruker, 2013) for (I), (II); CrysAlis RED (Agilent, 2012) for (III). Program(s) used to solve structure: SUPERFLIP Palatinus & Chapuis, 2007; Palatinus & van der Lee, 2008) for (I), (III); SUPERFLIP (Palatinus & Chapuis, 2007; Palatinus & van der Lee, 2008) for (II). For all structures, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009). Software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009) for (I), (II); PLATON (Spek, 2009) and SHELXL2014 (Sheldrick, 2015) for (III).

6-Amino-5-chloro-2,4-dimethylpyridin-1-ium 5-chloro-2-hydroxybenzoate (I)

Crystal data

C6H9ClN3^+·C7H4ClO3^−	Z = 4
Mr = 330.16	F(000) = 680
Triclinic, P1	Dx = 1.532 Mg m^−3
a = 9.3874 (4) Å	Cu Kα radiation, λ = 1.54178 Å
b = 10.5102 (4) Å	Cell parameters from 4963 reflections
c = 15.4295 (6) Å	θ = 3.0–66.6°
α = 71.167 (1)°	µ = 4.22 mm^−1
β = 83.335 (2)°	T = 100 K
γ = 87.730 (1)°	Needle, colourless
V = 1431.09 (10) Å^3	0.24 × 0.07 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer	4962 independent reflections
Radiation source: fine-focus sealed tube	4460 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω scans	θmax = 66.6°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −11→11
Tmin = 0.654, Tmax = 0.810	k = −12→10
18796 measured reflections	l = −18→18

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.081	w = 1/[σ^2(Fo^2) + (0.0284P)^2 + 1.245P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
4962 reflections	Δρmax = 0.34 e Å^−3
407 parameters	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
N11	1.02592 (16)	0.52970 (15)	0.12086 (10)	0.0201 (3)
C12	0.89213 (19)	0.56943 (18)	0.12706 (12)	0.0190 (4)
N13	0.80979 (16)	0.54908 (15)	0.20861 (10)	0.0184 (3)
H13	0.709 (2)	0.579 (2)	0.2083 (14)	0.022*
C14	0.86161 (19)	0.48424 (18)	0.29006 (12)	0.0188 (4)
C15	1.00531 (19)	0.44032 (18)	0.28493 (12)	0.0190 (4)
Cl15	1.07360 (5)	0.35441 (5)	0.38717 (3)	0.02719 (12)
C16	1.08401 (19)	0.46291 (18)	0.20063 (12)	0.0189 (4)
C121	0.8235 (2)	0.6413 (2)	0.04175 (12)	0.0241 (4)
H12A	0.8582	0.6030	−0.0069	0.036*
H12B	0.8482	0.7370	0.0215	0.036*
H12C	0.7191	0.6312	0.0548	0.036*
N14	0.77572 (18)	0.46578 (17)	0.36681 (11)	0.0228 (3)
H14B	0.684 (3)	0.493 (2)	0.3633 (15)	0.027*
H14A	0.809 (2)	0.425 (2)	0.4170 (16)	0.027*
C161	1.2341 (2)	0.4139 (2)	0.18923 (14)	0.0249 (4)
H16A	1.2872	0.4773	0.1351	0.037*
H16B	1.2328	0.3254	0.1808	0.037*
H16C	1.2808	0.4067	0.2442	0.037*
N21	0.33481 (17)	0.14191 (16)	0.71858 (11)	0.0242 (3)
C22	0.3861 (2)	0.16006 (19)	0.63259 (13)	0.0232 (4)
N23	0.51357 (16)	0.10973 (16)	0.60814 (11)	0.0221 (3)
H23	0.543 (2)	0.128 (2)	0.5403 (16)	0.027*
C24	0.5991 (2)	0.03751 (18)	0.67171 (13)	0.0221 (4)
C25	0.5464 (2)	0.01743 (18)	0.76476 (13)	0.0220 (4)
Cl25	0.65260 (5)	−0.07187 (5)	0.84854 (3)	0.02810 (12)
C26	0.4159 (2)	0.06952 (19)	0.78613 (13)	0.0230 (4)
C221	0.3027 (2)	0.2381 (2)	0.55594 (14)	0.0304 (5)
H22A	0.2406	0.3029	0.5758	0.046*
H22B	0.2438	0.1765	0.5393	0.046*
H22C	0.3690	0.2861	0.5024	0.046*
N24	0.72276 (18)	−0.00753 (18)	0.64309 (13)	0.0276 (4)
H24B	0.751 (3)	0.016 (2)	0.5802 (18)	0.033*
H24A	0.780 (3)	−0.043 (2)	0.6811 (17)	0.033*
C261	0.3559 (2)	0.0530 (2)	0.88334 (14)	0.0292 (4)
H26A	0.3680	−0.0405	0.9218	0.044*
H26B	0.2536	0.0760	0.8852	0.044*
H26C	0.4067	0.1127	0.9067	0.044*
C31	0.31187 (19)	0.67355 (18)	0.27484 (12)	0.0182 (4)
C32	0.2223 (2)	0.66823 (19)	0.35563 (12)	0.0210 (4)
C33	0.0865 (2)	0.7266 (2)	0.34955 (13)	0.0247 (4)
H33	0.0260	0.7218	0.4043	0.030*
C34	0.0386 (2)	0.79131 (19)	0.26498 (13)	0.0234 (4)
H34	−0.0543	0.8307	0.2611	0.028*
C35	0.1290 (2)	0.79779 (18)	0.18564 (12)	0.0201 (4)
Cl35	0.07191 (5)	0.88579 (5)	0.07862 (3)	0.02524 (12)
C36	0.26328 (19)	0.73941 (17)	0.18960 (12)	0.0185 (4)
H36	0.3225	0.7441	0.1344	0.022*
C37	0.45865 (19)	0.61226 (18)	0.27996 (13)	0.0207 (4)
O31	0.53626 (13)	0.62162 (14)	0.20630 (9)	0.0237 (3)
O32	0.49630 (14)	0.55505 (14)	0.36027 (9)	0.0277 (3)
O33	0.26546 (15)	0.60848 (15)	0.44005 (9)	0.0278 (3)
H33A	0.358 (3)	0.577 (2)	0.4305 (17)	0.042*
C41	0.7494 (2)	0.17511 (19)	0.30036 (13)	0.0233 (4)
C42	0.8866 (2)	0.1437 (2)	0.26513 (14)	0.0253 (4)
C43	0.9240 (2)	0.1812 (2)	0.17049 (14)	0.0279 (4)
H43	1.0163	0.1588	0.1471	0.033*
C44	0.8285 (2)	0.2506 (2)	0.11015 (14)	0.0275 (4)
H44	0.8551	0.2772	0.0455	0.033*
C45	0.6931 (2)	0.28109 (19)	0.14496 (14)	0.0255 (4)
Cl45	0.57379 (5)	0.36671 (5)	0.06714 (3)	0.03388 (13)
C46	0.6530 (2)	0.24430 (18)	0.23872 (14)	0.0240 (4)
H46	0.5599	0.2660	0.2613	0.029*
C47	0.7070 (2)	0.13490 (19)	0.40214 (14)	0.0254 (4)
O41	0.58295 (14)	0.16233 (14)	0.43069 (9)	0.0283 (3)
O42	0.80090 (15)	0.07389 (15)	0.45412 (10)	0.0339 (3)
O43	0.98479 (15)	0.07879 (15)	0.32111 (10)	0.0327 (3)
H43A	0.942 (3)	0.066 (3)	0.3819 (19)	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0176 (8)	0.0250 (8)	0.0203 (8)	−0.0017 (6)	0.0017 (6)	−0.0122 (6)
C12	0.0202 (9)	0.0223 (9)	0.0172 (9)	−0.0038 (7)	0.0014 (7)	−0.0110 (7)
N13	0.0142 (8)	0.0253 (8)	0.0174 (8)	−0.0006 (6)	0.0005 (6)	−0.0097 (6)
C14	0.0198 (9)	0.0203 (9)	0.0179 (9)	−0.0030 (7)	0.0002 (7)	−0.0088 (7)
C15	0.0185 (9)	0.0190 (9)	0.0206 (9)	−0.0004 (7)	−0.0024 (7)	−0.0076 (7)
Cl15	0.0249 (2)	0.0310 (3)	0.0225 (2)	0.00505 (18)	−0.00374 (18)	−0.00438 (19)
C16	0.0176 (9)	0.0182 (9)	0.0241 (10)	−0.0025 (7)	0.0010 (7)	−0.0121 (7)
C121	0.0183 (9)	0.0376 (11)	0.0174 (9)	−0.0003 (8)	0.0008 (7)	−0.0113 (8)
N14	0.0183 (8)	0.0320 (9)	0.0163 (8)	0.0012 (7)	0.0008 (6)	−0.0065 (7)
C161	0.0205 (10)	0.0280 (10)	0.0286 (10)	0.0038 (8)	−0.0004 (8)	−0.0138 (8)
N21	0.0204 (8)	0.0258 (9)	0.0277 (9)	0.0009 (6)	0.0021 (7)	−0.0123 (7)
C22	0.0202 (9)	0.0224 (10)	0.0293 (10)	−0.0007 (7)	0.0016 (8)	−0.0128 (8)
N23	0.0199 (8)	0.0236 (8)	0.0239 (9)	−0.0004 (6)	0.0022 (6)	−0.0108 (7)
C24	0.0194 (9)	0.0190 (9)	0.0299 (10)	−0.0038 (7)	0.0011 (8)	−0.0114 (8)
C25	0.0211 (9)	0.0179 (9)	0.0275 (10)	−0.0030 (7)	−0.0005 (8)	−0.0083 (8)
Cl25	0.0285 (3)	0.0252 (2)	0.0290 (3)	0.00219 (18)	−0.00214 (19)	−0.00696 (19)
C26	0.0220 (10)	0.0205 (9)	0.0280 (10)	−0.0051 (7)	0.0030 (8)	−0.0111 (8)
C221	0.0247 (10)	0.0368 (12)	0.0316 (11)	0.0083 (9)	−0.0017 (9)	−0.0150 (9)
N24	0.0206 (9)	0.0348 (10)	0.0284 (10)	0.0049 (7)	0.0002 (7)	−0.0128 (8)
C261	0.0291 (11)	0.0314 (11)	0.0259 (11)	−0.0003 (8)	0.0055 (8)	−0.0103 (9)
C31	0.0174 (9)	0.0188 (9)	0.0195 (9)	−0.0040 (7)	0.0016 (7)	−0.0084 (7)
C32	0.0212 (9)	0.0242 (10)	0.0175 (9)	−0.0033 (7)	0.0004 (7)	−0.0069 (7)
C33	0.0225 (10)	0.0317 (11)	0.0192 (9)	0.0027 (8)	0.0046 (7)	−0.0101 (8)
C34	0.0204 (9)	0.0247 (10)	0.0259 (10)	0.0040 (7)	0.0000 (8)	−0.0109 (8)
C35	0.0228 (9)	0.0193 (9)	0.0186 (9)	−0.0007 (7)	−0.0027 (7)	−0.0066 (7)
Cl35	0.0268 (2)	0.0273 (2)	0.0198 (2)	0.00532 (18)	−0.00396 (18)	−0.00508 (18)
C36	0.0190 (9)	0.0203 (9)	0.0173 (9)	−0.0034 (7)	0.0019 (7)	−0.0086 (7)
C37	0.0174 (9)	0.0235 (10)	0.0214 (10)	−0.0041 (7)	0.0005 (7)	−0.0081 (8)
O31	0.0169 (6)	0.0360 (8)	0.0186 (7)	0.0007 (5)	0.0013 (5)	−0.0103 (6)
O32	0.0195 (7)	0.0404 (8)	0.0191 (7)	0.0031 (6)	−0.0004 (5)	−0.0048 (6)
O33	0.0218 (7)	0.0433 (8)	0.0160 (7)	0.0045 (6)	0.0002 (5)	−0.0078 (6)
C41	0.0223 (10)	0.0201 (9)	0.0295 (10)	−0.0048 (7)	0.0067 (8)	−0.0133 (8)
C42	0.0215 (10)	0.0258 (10)	0.0326 (11)	−0.0009 (8)	0.0017 (8)	−0.0164 (8)
C43	0.0205 (10)	0.0336 (11)	0.0335 (11)	−0.0027 (8)	0.0071 (8)	−0.0194 (9)
C44	0.0269 (10)	0.0306 (11)	0.0277 (10)	−0.0074 (8)	0.0073 (8)	−0.0156 (9)
C45	0.0263 (10)	0.0215 (10)	0.0288 (10)	−0.0048 (8)	0.0018 (8)	−0.0094 (8)
Cl45	0.0268 (3)	0.0377 (3)	0.0317 (3)	0.0000 (2)	0.0032 (2)	−0.0058 (2)
C46	0.0202 (9)	0.0197 (9)	0.0329 (11)	−0.0023 (7)	0.0065 (8)	−0.0125 (8)
C47	0.0237 (10)	0.0236 (10)	0.0305 (11)	−0.0035 (8)	0.0050 (8)	−0.0130 (8)
O41	0.0230 (7)	0.0333 (8)	0.0274 (7)	0.0007 (6)	0.0069 (6)	−0.0113 (6)
O42	0.0274 (8)	0.0432 (9)	0.0295 (8)	0.0069 (6)	0.0033 (6)	−0.0124 (7)
O43	0.0242 (7)	0.0437 (9)	0.0318 (8)	0.0070 (6)	0.0020 (6)	−0.0168 (7)

Geometric parameters (Å, º)

N11—C12	1.310 (2)	C221—H22C	0.9800
C12—N13	1.357 (2)	N24—H24B	0.93 (3)
C12—C121	1.495 (3)	N24—H24A	0.83 (2)
N13—C14	1.358 (2)	C261—H26A	0.9800
N13—H13	0.99 (2)	C261—H26B	0.9800
C14—C15	1.410 (3)	C261—H26C	0.9800
C15—C16	1.373 (3)	C31—C36	1.394 (3)
C16—N11	1.368 (2)	C31—C32	1.407 (2)
C14—N14	1.316 (2)	C31—C37	1.497 (3)
C15—Cl15	1.7274 (18)	C32—O33	1.353 (2)
C16—C161	1.491 (3)	C32—C33	1.392 (3)
C121—H12A	0.9800	C33—C34	1.381 (3)
C121—H12B	0.9800	C33—H33	0.9500
C121—H12C	0.9800	C34—C35	1.390 (3)
N14—H14B	0.90 (2)	C34—H34	0.9500
N14—H14A	0.84 (2)	C35—C36	1.379 (3)
C161—H16A	0.9800	C35—Cl35	1.7462 (18)
C161—H16B	0.9800	C36—H36	0.9500
C161—H16C	0.9800	O33—H33A	0.93 (3)
C37—O31	1.254 (2)	C41—C46	1.398 (3)
C37—O32	1.275 (2)	C41—C42	1.408 (3)
N21—C22	1.313 (3)	C41—C47	1.498 (3)
C22—N23	1.352 (2)	C42—O43	1.348 (2)
C22—C221	1.490 (3)	C42—C43	1.390 (3)
N23—C24	1.355 (3)	C43—C44	1.381 (3)
N23—H23	1.01 (2)	C43—H43	0.9500
C24—C25	1.414 (3)	C44—C45	1.388 (3)
C25—C26	1.371 (3)	C44—H44	0.9500
C25—Cl25	1.7284 (19)	C45—C46	1.381 (3)
C26—N21	1.368 (3)	C45—Cl45	1.743 (2)
C24—N24	1.319 (3)	C46—H46	0.9500
C26—C261	1.497 (3)	C47—O41	1.253 (2)
C221—H22A	0.9800	C47—O42	1.272 (2)
C221—H22B	0.9800	O43—H43A	0.95 (3)
C12—N11—C16	118.13 (15)	C24—N24—H24B	119.2 (15)
N11—C12—N13	123.10 (17)	C24—N24—H24A	118.8 (17)
N11—C12—C121	120.06 (16)	H24B—N24—H24A	121 (2)
N13—C12—C121	116.84 (16)	C26—C261—H26A	109.5
C12—N13—C14	121.51 (16)	C26—C261—H26B	109.5
C12—N13—H13	118.9 (12)	H26A—C261—H26B	109.5
C14—N13—H13	119.5 (12)	C26—C261—H26C	109.5
N14—C14—N13	118.63 (17)	H26A—C261—H26C	109.5
N14—C14—C15	125.05 (17)	H26B—C261—H26C	109.5
N13—C14—C15	116.31 (16)	C36—C31—C32	119.03 (17)
C16—C15—C14	119.94 (17)	C36—C31—C37	120.27 (16)
C16—C15—Cl15	122.50 (14)	C32—C31—C37	120.68 (16)
C14—C15—Cl15	117.53 (14)	O33—C32—C33	118.64 (16)
N11—C16—C15	121.00 (16)	O33—C32—C31	121.46 (17)
N11—C16—C161	115.80 (16)	C33—C32—C31	119.89 (17)
C15—C16—C161	123.17 (17)	C34—C33—C32	120.89 (17)
C12—C121—H12A	109.5	C34—C33—H33	119.6
C12—C121—H12B	109.5	C32—C33—H33	119.6
H12A—C121—H12B	109.5	C33—C34—C35	118.70 (17)
C12—C121—H12C	109.5	C33—C34—H34	120.6
H12A—C121—H12C	109.5	C35—C34—H34	120.6
H12B—C121—H12C	109.5	C36—C35—C34	121.66 (17)
C14—N14—H14B	118.9 (14)	C36—C35—Cl35	119.47 (14)
C14—N14—H14A	117.9 (15)	C34—C35—Cl35	118.86 (14)
H14B—N14—H14A	123 (2)	C35—C36—C31	119.82 (16)
C16—C161—H16A	109.5	C35—C36—H36	120.1
C16—C161—H16B	109.5	C31—C36—H36	120.1
H16A—C161—H16B	109.5	O31—C37—O32	124.59 (17)
C16—C161—H16C	109.5	O31—C37—C31	118.68 (16)
H16A—C161—H16C	109.5	O32—C37—C31	116.73 (16)
H16B—C161—H16C	109.5	C32—O33—H33A	106.5 (15)
C22—N21—C26	117.86 (16)	C46—C41—C42	118.90 (18)
N21—C22—N23	123.21 (18)	C46—C41—C47	120.39 (17)
N21—C22—C221	120.37 (17)	C42—C41—C47	120.71 (18)
N23—C22—C221	116.42 (17)	O43—C42—C43	118.41 (17)
C22—N23—C24	121.81 (17)	O43—C42—C41	121.61 (18)
C22—N23—H23	117.2 (12)	C43—C42—C41	119.98 (19)
C24—N23—H23	121.0 (12)	C44—C43—C42	120.70 (18)
N24—C24—N23	118.67 (18)	C44—C43—H43	119.6
N24—C24—C25	125.39 (19)	C42—C43—H43	119.6
N23—C24—C25	115.94 (16)	C43—C44—C45	119.27 (18)
C26—C25—C24	120.10 (18)	C43—C44—H44	120.4
C26—C25—Cl25	122.09 (15)	C45—C44—H44	120.4
C24—C25—Cl25	117.80 (14)	C46—C45—C44	121.13 (19)
N21—C26—C25	121.08 (17)	C46—C45—Cl45	120.59 (15)
N21—C26—C261	116.56 (16)	C44—C45—Cl45	118.28 (16)
C25—C26—C261	122.36 (18)	C45—C46—C41	120.01 (17)
C22—C221—H22A	109.5	C45—C46—H46	120.0
C22—C221—H22B	109.5	C41—C46—H46	120.0
H22A—C221—H22B	109.5	O41—C47—O42	124.30 (18)
C22—C221—H22C	109.5	O41—C47—C41	118.74 (18)
H22A—C221—H22C	109.5	O42—C47—C41	116.97 (17)
H22B—C221—H22C	109.5	C42—O43—H43A	105.9 (16)
C16—N11—C12—N13	1.0 (3)	C37—C31—C32—O33	0.2 (3)
C16—N11—C12—C121	−179.28 (16)	C36—C31—C32—C33	0.9 (3)
N11—C12—N13—C14	−0.6 (3)	C37—C31—C32—C33	179.55 (17)
C121—C12—N13—C14	179.67 (16)	O33—C32—C33—C34	178.59 (17)
C12—N13—C14—N14	−178.96 (16)	C31—C32—C33—C34	−0.7 (3)
C12—N13—C14—C15	0.4 (2)	C32—C33—C34—C35	−0.3 (3)
N14—C14—C15—C16	178.65 (17)	C33—C34—C35—C36	1.1 (3)
N13—C14—C15—C16	−0.6 (2)	C33—C34—C35—Cl35	−177.27 (14)
N14—C14—C15—Cl15	0.6 (3)	C34—C35—C36—C31	−0.9 (3)
N13—C14—C15—Cl15	−178.70 (12)	Cl35—C35—C36—C31	177.47 (13)
C12—N11—C16—C15	−1.2 (2)	C32—C31—C36—C35	−0.1 (3)
C12—N11—C16—C161	176.96 (16)	C37—C31—C36—C35	−178.74 (16)
C14—C15—C16—N11	1.1 (3)	C36—C31—C37—O31	0.1 (3)
Cl15—C15—C16—N11	179.05 (13)	C32—C31—C37—O31	−178.54 (16)
C14—C15—C16—C161	−176.96 (17)	C36—C31—C37—O32	179.22 (16)
Cl15—C15—C16—C161	1.0 (3)	C32—C31—C37—O32	0.6 (3)
C26—N21—C22—N23	0.7 (3)	C46—C41—C42—O43	179.08 (17)
C26—N21—C22—C221	−179.99 (17)	C47—C41—C42—O43	−1.1 (3)
N21—C22—N23—C24	−0.9 (3)	C46—C41—C42—C43	−0.1 (3)
C221—C22—N23—C24	179.77 (17)	C47—C41—C42—C43	179.69 (17)
C22—N23—C24—N24	−179.35 (17)	O43—C42—C43—C44	−178.50 (17)
C22—N23—C24—C25	0.4 (3)	C41—C42—C43—C44	0.7 (3)
N24—C24—C25—C26	179.88 (18)	C42—C43—C44—C45	−1.0 (3)
N23—C24—C25—C26	0.1 (3)	C43—C44—C45—C46	0.6 (3)
N24—C24—C25—Cl25	0.7 (3)	C43—C44—C45—Cl45	−179.10 (15)
N23—C24—C25—Cl25	−179.04 (13)	C44—C45—C46—C41	0.0 (3)
C22—N21—C26—C25	−0.1 (3)	Cl45—C45—C46—C41	179.69 (14)
C22—N21—C26—C261	178.79 (17)	C42—C41—C46—C45	−0.2 (3)
C24—C25—C26—N21	−0.3 (3)	C47—C41—C46—C45	179.95 (17)
Cl25—C25—C26—N21	178.83 (13)	C46—C41—C47—O41	1.3 (3)
C24—C25—C26—C261	−179.11 (17)	C42—C41—C47—O41	−178.55 (17)
Cl25—C25—C26—C261	0.0 (3)	C46—C41—C47—O42	−179.02 (17)
C36—C31—C32—O33	−178.37 (16)	C42—C41—C47—O42	1.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N13—H13···O31	0.985 (19)	1.666 (19)	2.650 (2)	177 (2)
N14—H14A···O33^i	0.84 (2)	2.15 (2)	2.810 (2)	134.4 (18)
N14—H14B···O32	0.90 (3)	1.86 (3)	2.753 (2)	176.7 (15)
O33—H33A···O32	0.93 (3)	1.65 (3)	2.502 (2)	150 (2)
N23—H23···O41	1.01 (2)	1.61 (2)	2.620 (2)	177.0 (17)
N24—H24A···O43^ii	0.83 (3)	2.22 (3)	2.885 (2)	137 (2)
N24—H24B···O42	0.93 (3)	1.85 (3)	2.777 (2)	176 (2)
O43—H43A···O42	0.95 (3)	1.65 (3)	2.512 (2)	150 (3)

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

4-Amino-5-chloro-2,6-dimethylpyridin-1-ium 5-chloro-2-hydroxybenzoate (II)

Crystal data

C6H9ClN3^+·C7H4ClO3^−	F(000) = 1360
Mr = 330.16	Dx = 1.510 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 24.7483 (12) Å	Cell parameters from 5117 reflections
b = 6.9525 (3) Å	θ = 1.9–66.9°
c = 18.1423 (8) Å	µ = 4.16 mm^−1
β = 111.500 (3)°	T = 100 K
V = 2904.4 (2) Å^3	Block, colourless
Z = 8	0.10 × 0.04 × 0.04 mm

Data collection

Rigaku Oxford Diffration Gemini diffractometer	5116 independent reflections
Radiation source: fine-focus sealed tube	4647 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
ω scans	θmax = 66.9°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −28→29
Tmin = 0.683, Tmax = 0.847	k = −8→8
19622 measured reflections	l = −21→21

Refinement

Refinement on F^2	50 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.0624P)^2 + 1.794P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.043
5116 reflections	Δρmax = 0.51 e Å^−3
454 parameters	Δρmin = −0.40 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.

Refinement. Refined as a 2-component twin.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N11	0.67190 (12)	0.3050 (4)	0.61584 (17)	0.0126 (5)
H11	0.7067	0.2839	0.6148	0.015*
C12	0.62749 (15)	0.3456 (4)	0.5477 (2)	0.0131 (6)
N13	0.57455 (12)	0.3790 (4)	0.54442 (16)	0.0140 (5)
C14	0.56348 (14)	0.3675 (5)	0.6130 (2)	0.0139 (6)
C15	0.60904 (14)	0.3248 (4)	0.68556 (19)	0.0130 (6)
Cl15	0.59493 (4)	0.31775 (13)	0.77160 (5)	0.0182 (2)
C16	0.66393 (16)	0.2960 (5)	0.6869 (2)	0.0143 (7)
C121	0.64070 (15)	0.3500 (5)	0.4738 (2)	0.0162 (7)
H12A	0.6047	0.3696	0.4281	0.024*
H12B	0.6584	0.2276	0.4680	0.024*
H12C	0.6677	0.4555	0.4769	0.024*
N14	0.50929 (11)	0.3982 (4)	0.60751 (17)	0.0172 (6)
H14A	0.4823	0.4245	0.5612	0.021*
H14B	0.5003	0.3922	0.6501	0.021*
C161	0.7158 (2)	0.2559 (4)	0.7604 (3)	0.0143 (9)
H16A	0.7064	0.1529	0.7907	0.021*
H16B	0.7263	0.3726	0.7929	0.021*
H16C	0.7485	0.2160	0.7457	0.021*
N21	0.17238 (13)	0.1844 (5)	0.5546 (2)	0.0158 (7)	0.836 (2)
H21	0.2075	0.2014	0.5902	0.019*	0.836 (2)
C22	0.12770 (15)	0.1485 (5)	0.5792 (2)	0.0136 (8)	0.836 (2)
N23	0.07439 (13)	0.1174 (5)	0.52944 (19)	0.0152 (7)	0.836 (2)
C24	0.06323 (15)	0.1288 (5)	0.4504 (2)	0.0144 (8)	0.836 (2)
C25	0.10910 (18)	0.1684 (5)	0.4233 (2)	0.0153 (8)	0.836 (2)
Cl25	0.09450 (4)	0.17614 (15)	0.32246 (5)	0.0200 (3)	0.836 (2)
C26	0.16424 (17)	0.1945 (6)	0.4765 (2)	0.0145 (8)	0.836 (2)
C221	0.14065 (17)	0.1442 (6)	0.6665 (2)	0.0206 (9)	0.836 (2)
H22A	0.1042	0.1445	0.6760	0.031*	0.836 (2)
H22B	0.1636	0.2577	0.6913	0.031*	0.836 (2)
H22C	0.1627	0.0275	0.6892	0.031*	0.836 (2)
N24	0.00906 (13)	0.1014 (5)	0.40204 (19)	0.0202 (7)	0.836 (2)
H24A	−0.0180	0.0769	0.4214	0.024*	0.836 (2)
H24B	0.0000	0.1075	0.3505	0.024*	0.836 (2)
C261	0.2162 (2)	0.2223 (6)	0.4556 (4)	0.0190 (15)	0.836 (2)
H26A	0.2099	0.3318	0.4194	0.028*	0.836 (2)
H26B	0.2231	0.1060	0.4298	0.028*	0.836 (2)
H26C	0.2501	0.2475	0.5039	0.028*	0.836 (2)
N51	0.1719 (4)	0.304 (3)	0.5545 (5)	0.0158 (7)	0.164 (2)
H51A	0.2070	0.2873	0.5902	0.019*	0.164 (2)
C52	0.1274 (4)	0.345 (3)	0.5787 (5)	0.0136 (8)	0.164 (2)
N53	0.0745 (4)	0.384 (2)	0.5294 (5)	0.0152 (7)	0.164 (2)
C54	0.0633 (4)	0.370 (3)	0.4503 (5)	0.0144 (8)	0.164 (2)
C55	0.1089 (4)	0.323 (3)	0.4236 (4)	0.0153 (8)	0.164 (2)
Cl55	0.0950 (2)	0.3186 (8)	0.3228 (2)	0.0200 (3)	0.164 (2)
C56	0.1635 (4)	0.287 (3)	0.4765 (5)	0.0145 (8)	0.164 (2)
C521	0.1401 (6)	0.350 (3)	0.6661 (5)	0.0206 (9)	0.164 (2)
H52A	0.1374	0.4831	0.6825	0.031*	0.164 (2)
H52B	0.1793	0.3010	0.6947	0.031*	0.164 (2)
H52C	0.1118	0.2703	0.6782	0.031*	0.164 (2)
N54	0.0095 (4)	0.405 (2)	0.4026 (7)	0.0202 (7)	0.164 (2)
H54A	−0.0169	0.4355	0.4224	0.024*	0.164 (2)
H54B	0.0000	0.3976	0.3509	0.024*	0.164 (2)
C561	0.2162 (6)	0.275 (5)	0.4560 (10)	0.0190 (15)	0.164 (2)
H56A	0.2410	0.1696	0.4859	0.028*	0.164 (2)
H56B	0.2377	0.3963	0.4695	0.028*	0.164 (2)
H56C	0.2048	0.2503	0.3991	0.028*	0.164 (2)
C31	0.36550 (15)	0.3020 (5)	0.7575 (2)	0.0141 (7)
C32	0.42308 (15)	0.3326 (4)	0.7633 (2)	0.0159 (7)
C33	0.46632 (15)	0.3692 (5)	0.8368 (2)	0.0196 (7)
H33	0.5051	0.3914	0.8406	0.024*
C34	0.45269 (16)	0.3729 (5)	0.9038 (2)	0.0196 (7)
H34	0.4824	0.3963	0.9539	0.024*
C35	0.39593 (16)	0.3429 (4)	0.8989 (2)	0.0167 (7)
Cl35	0.37899 (4)	0.34859 (12)	0.98413 (5)	0.0235 (2)
C36	0.35252 (16)	0.3081 (5)	0.8261 (2)	0.0156 (7)
H36	0.3137	0.2883	0.8229	0.019*
C37	0.3194 (2)	0.2614 (4)	0.6772 (3)	0.0140 (9)
O31	0.26786 (15)	0.2385 (4)	0.6765 (2)	0.0233 (8)
O32	0.33368 (17)	0.2549 (4)	0.6187 (2)	0.0264 (9)
O33	0.43709 (11)	0.3267 (4)	0.69768 (15)	0.0219 (5)
H33A	0.4078	0.2936	0.6585	0.033*
C41	0.86524 (17)	0.3106 (6)	0.6068 (2)	0.0146 (8)	0.834 (2)
C42	0.92287 (17)	0.3364 (5)	0.6592 (2)	0.0187 (8)	0.834 (2)
C43	0.96595 (17)	0.3699 (6)	0.6284 (3)	0.0243 (9)	0.834 (2)
H43	1.0048	0.3916	0.6635	0.029*	0.834 (2)
C44	0.95295 (18)	0.3719 (6)	0.5474 (3)	0.0225 (9)	0.834 (2)
H44	0.9828	0.3893	0.5269	0.027*	0.834 (2)
C45	0.89526 (19)	0.3479 (6)	0.4962 (2)	0.0195 (9)	0.834 (2)
Cl45	0.87834 (5)	0.35384 (15)	0.39354 (6)	0.0265 (3)	0.834 (2)
C46	0.85207 (18)	0.3180 (6)	0.5257 (2)	0.0168 (8)	0.834 (2)
H46	0.8130	0.3023	0.4904	0.020*	0.834 (2)
C47	0.8174 (2)	0.2757 (7)	0.6366 (3)	0.0159 (15)	0.834 (2)
O41	0.76736 (17)	0.2615 (6)	0.5892 (3)	0.0190 (12)	0.834 (2)
O42	0.8328 (3)	0.260 (8)	0.7130 (5)	0.0244 (10)	0.834 (2)
O43	0.93656 (13)	0.3302 (5)	0.73796 (17)	0.0235 (7)	0.834 (2)
H43A	0.9066	0.3060	0.7478	0.035*	0.834 (2)
C61	0.8666 (4)	0.211 (3)	0.6092 (5)	0.0146 (8)	0.166 (2)
C62	0.9230 (5)	0.161 (3)	0.6612 (5)	0.0187 (8)	0.166 (2)
C63	0.9659 (5)	0.128 (3)	0.6300 (5)	0.0243 (9)	0.166 (2)
H63	1.0042	0.0973	0.6646	0.029*	0.166 (2)
C64	0.9533 (4)	0.138 (3)	0.5492 (5)	0.0225 (9)	0.166 (2)
H64	0.9835	0.1308	0.5288	0.027*	0.166 (2)
C65	0.8954 (4)	0.159 (3)	0.4979 (4)	0.0195 (9)	0.166 (2)
Cl65	0.8788 (2)	0.1496 (7)	0.3952 (3)	0.0265 (3)	0.166 (2)
C66	0.8525 (4)	0.187 (3)	0.5283 (5)	0.0168 (8)	0.166 (2)
H66	0.8129	0.1899	0.4936	0.020*	0.166 (2)
C67	0.8185 (6)	0.225 (5)	0.6400 (9)	0.0140 (9)	0.166 (2)
O61	0.7680 (5)	0.218 (5)	0.5937 (14)	0.0190 (12)	0.166 (2)
O62	0.8343 (12)	0.26 (4)	0.715 (2)	0.0244 (10)	0.166 (2)
O63	0.9365 (5)	0.169 (2)	0.7397 (5)	0.0235 (7)	0.166 (2)
H63A	0.9083	0.1286	0.7506	0.035*	0.166 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N11	0.0130 (13)	0.0151 (13)	0.0132 (14)	−0.0002 (10)	0.0090 (11)	−0.0006 (10)
C12	0.0159 (15)	0.0087 (13)	0.0159 (16)	−0.0001 (10)	0.0071 (13)	−0.0001 (11)
N13	0.0158 (13)	0.0165 (12)	0.0114 (13)	0.0016 (10)	0.0071 (10)	0.0026 (9)
C14	0.0200 (16)	0.0101 (13)	0.0153 (16)	−0.0019 (11)	0.0107 (13)	−0.0003 (11)
C15	0.0165 (16)	0.0126 (16)	0.0111 (16)	−0.0025 (11)	0.0067 (13)	0.0022 (11)
Cl15	0.0228 (5)	0.0229 (4)	0.0124 (4)	0.0009 (3)	0.0105 (3)	0.0025 (3)
C16	0.0201 (18)	0.0088 (13)	0.0134 (18)	−0.0030 (13)	0.0056 (14)	−0.0007 (13)
C121	0.0195 (17)	0.0203 (16)	0.0115 (16)	0.0009 (11)	0.0088 (14)	0.0020 (11)
N14	0.0148 (13)	0.0244 (15)	0.0146 (13)	0.0029 (10)	0.0081 (11)	0.0045 (10)
C161	0.012 (2)	0.019 (2)	0.010 (2)	−0.0012 (11)	0.0022 (19)	0.0001 (10)
N21	0.0088 (15)	0.0209 (18)	0.0203 (18)	−0.0025 (14)	0.0084 (14)	−0.0020 (15)
C22	0.0108 (17)	0.0159 (18)	0.0140 (19)	−0.0012 (12)	0.0044 (15)	−0.0003 (13)
N23	0.0113 (14)	0.0203 (16)	0.0155 (16)	0.0016 (12)	0.0069 (12)	0.0005 (11)
C24	0.0113 (17)	0.0164 (17)	0.0151 (19)	0.0009 (13)	0.0042 (15)	0.0030 (13)
C25	0.0171 (19)	0.0164 (19)	0.014 (2)	−0.0003 (14)	0.0072 (16)	0.0011 (13)
Cl25	0.0198 (6)	0.0276 (5)	0.0128 (6)	−0.0023 (4)	0.0063 (4)	0.0008 (3)
C26	0.0151 (19)	0.013 (2)	0.017 (2)	0.0013 (18)	0.0076 (16)	0.0011 (18)
C221	0.0124 (19)	0.031 (2)	0.016 (2)	−0.0024 (14)	0.0033 (15)	−0.0026 (15)
N24	0.0120 (15)	0.0308 (19)	0.0142 (16)	−0.0038 (12)	0.0006 (12)	0.0011 (12)
C261	0.019 (3)	0.015 (3)	0.027 (3)	−0.0013 (16)	0.014 (2)	0.0012 (17)
N51	0.0088 (15)	0.0209 (18)	0.0203 (18)	−0.0025 (14)	0.0084 (14)	−0.0020 (15)
C52	0.0108 (17)	0.0159 (18)	0.0140 (19)	−0.0012 (12)	0.0044 (15)	−0.0003 (13)
N53	0.0113 (14)	0.0203 (16)	0.0155 (16)	0.0016 (12)	0.0069 (12)	0.0005 (11)
C54	0.0113 (17)	0.0164 (17)	0.0151 (19)	0.0009 (13)	0.0042 (15)	0.0030 (13)
C55	0.0171 (19)	0.0164 (19)	0.014 (2)	−0.0003 (14)	0.0072 (16)	0.0011 (13)
Cl55	0.0198 (6)	0.0276 (5)	0.0128 (6)	−0.0023 (4)	0.0063 (4)	0.0008 (3)
C56	0.0151 (19)	0.013 (2)	0.017 (2)	0.0013 (18)	0.0076 (16)	0.0011 (18)
C521	0.0124 (19)	0.031 (2)	0.016 (2)	−0.0024 (14)	0.0033 (15)	−0.0026 (15)
N54	0.0120 (15)	0.0308 (19)	0.0142 (16)	−0.0038 (12)	0.0006 (12)	0.0011 (12)
C561	0.019 (3)	0.015 (3)	0.027 (3)	−0.0013 (16)	0.014 (2)	0.0012 (17)
C31	0.0174 (18)	0.0129 (14)	0.0115 (17)	−0.0005 (13)	0.0048 (14)	0.0037 (12)
C32	0.0190 (17)	0.0126 (15)	0.0175 (17)	0.0017 (11)	0.0082 (14)	0.0006 (11)
C33	0.0171 (17)	0.0206 (15)	0.0203 (18)	−0.0009 (12)	0.0059 (14)	−0.0025 (12)
C34	0.0214 (16)	0.0207 (16)	0.0129 (16)	0.0044 (13)	0.0018 (13)	−0.0008 (12)
C35	0.0297 (18)	0.0104 (14)	0.0108 (16)	0.0035 (12)	0.0084 (14)	0.0011 (10)
Cl35	0.0383 (5)	0.0216 (4)	0.0129 (4)	0.0079 (3)	0.0121 (4)	0.0022 (3)
C36	0.0196 (17)	0.0133 (16)	0.0161 (17)	0.0004 (13)	0.0090 (14)	0.0042 (12)
C37	0.0119 (18)	0.0143 (18)	0.012 (2)	−0.0032 (11)	0.0004 (18)	0.0046 (11)
O31	0.0138 (18)	0.0394 (18)	0.017 (2)	−0.0079 (9)	0.0058 (16)	−0.0017 (9)
O32	0.021 (2)	0.049 (2)	0.0083 (18)	−0.0046 (10)	0.0042 (17)	−0.0005 (9)
O33	0.0181 (13)	0.0357 (15)	0.0153 (12)	−0.0056 (10)	0.0100 (10)	−0.0039 (10)
C41	0.012 (2)	0.011 (2)	0.021 (2)	−0.0008 (17)	0.0071 (16)	−0.0011 (17)
C42	0.0149 (19)	0.024 (2)	0.015 (2)	0.0032 (14)	0.0033 (17)	−0.0021 (15)
C43	0.013 (2)	0.030 (2)	0.030 (2)	0.0009 (16)	0.0084 (17)	0.0017 (17)
C44	0.0172 (19)	0.026 (2)	0.031 (2)	0.0035 (15)	0.0161 (18)	0.0051 (16)
C45	0.024 (2)	0.020 (2)	0.017 (2)	0.0046 (15)	0.0111 (17)	0.0017 (13)
Cl45	0.0359 (7)	0.0301 (6)	0.0181 (6)	0.0059 (4)	0.0153 (4)	0.0023 (3)
C46	0.0148 (19)	0.018 (2)	0.017 (2)	0.0002 (17)	0.0052 (16)	−0.0012 (16)
C47	0.023 (3)	0.015 (2)	0.010 (2)	0.0053 (17)	0.007 (2)	0.0054 (15)
O41	0.0129 (18)	0.025 (3)	0.020 (2)	−0.0007 (11)	0.0074 (17)	−0.0004 (15)
O42	0.020 (2)	0.039 (2)	0.015 (2)	−0.0010 (18)	0.0068 (18)	−0.002 (2)
O43	0.0151 (15)	0.0387 (18)	0.0158 (16)	−0.0034 (12)	0.0046 (11)	−0.0007 (12)
C61	0.012 (2)	0.011 (2)	0.021 (2)	−0.0008 (17)	0.0071 (16)	−0.0011 (17)
C62	0.0149 (19)	0.024 (2)	0.015 (2)	0.0032 (14)	0.0033 (17)	−0.0021 (15)
C63	0.013 (2)	0.030 (2)	0.030 (2)	0.0009 (16)	0.0084 (17)	0.0017 (17)
C64	0.0172 (19)	0.026 (2)	0.031 (2)	0.0035 (15)	0.0161 (18)	0.0051 (16)
C65	0.024 (2)	0.020 (2)	0.017 (2)	0.0046 (15)	0.0111 (17)	0.0017 (13)
Cl65	0.0359 (7)	0.0301 (6)	0.0181 (6)	0.0059 (4)	0.0153 (4)	0.0023 (3)
C66	0.0148 (19)	0.018 (2)	0.017 (2)	0.0002 (17)	0.0052 (16)	−0.0012 (16)
C67	0.0119 (18)	0.0143 (18)	0.012 (2)	−0.0032 (11)	0.0004 (18)	0.0046 (11)
O61	0.0129 (18)	0.025 (3)	0.020 (2)	−0.0007 (11)	0.0074 (17)	−0.0004 (15)
O62	0.020 (2)	0.039 (2)	0.015 (2)	−0.0010 (18)	0.0068 (18)	−0.002 (2)
O63	0.0151 (15)	0.0387 (18)	0.0158 (16)	−0.0034 (12)	0.0046 (11)	−0.0007 (12)

Geometric parameters (Å, º)

N11—C12	1.349 (4)	C521—H52A	0.9800
N11—H11	0.8800	C521—H52B	0.9800
C12—N13	1.310 (4)	C521—H52C	0.9800
C12—C121	1.492 (4)	N54—H54A	0.8800
N13—C14	1.371 (4)	N54—H54B	0.8800
C14—C15	1.416 (5)	C561—H56A	0.9800
C15—C16	1.365 (5)	C561—H56B	0.9800
C16—N11	1.375 (5)	C561—H56C	0.9800
C14—N14	1.325 (4)	C31—C36	1.395 (5)
C15—Cl15	1.721 (3)	C31—C32	1.406 (5)
C16—C161	1.499 (6)	C31—C37	1.512 (6)
C121—H12A	0.9800	C32—O33	1.356 (4)
C121—H12B	0.9800	C32—C33	1.394 (5)
C121—H12C	0.9800	C33—C34	1.375 (5)
N14—H14A	0.8800	C33—H33	0.9500
N14—H14B	0.8800	C34—C35	1.390 (5)
C161—H16A	0.9800	C34—H34	0.9500
C161—H16B	0.9800	C35—C36	1.384 (5)
C161—H16C	0.9800	C35—Cl35	1.745 (3)
C37—O31	1.281 (6)	C36—H36	0.9500
C37—O32	1.236 (7)	O33—H33A	0.8400
N21—C22	1.358 (5)	C41—C46	1.386 (6)
N21—H21	0.8800	C41—C42	1.406 (6)
C22—N23	1.315 (5)	C41—C47	1.489 (7)
C22—C221	1.496 (5)	C42—O43	1.343 (5)
N23—C24	1.360 (5)	C42—C43	1.393 (6)
C24—C25	1.420 (5)	C43—C44	1.384 (6)
C25—C26	1.364 (6)	C43—H43	0.9500
C26—N21	1.358 (5)	C44—C45	1.399 (6)
C24—N24	1.320 (5)	C44—H44	0.9500
C25—Cl25	1.731 (4)	C45—C46	1.376 (6)
C26—C261	1.480 (7)	C45—Cl45	1.754 (4)
C221—H22A	0.9800	C46—H46	0.9500
C221—H22B	0.9800	C47—O41	1.226 (6)
C221—H22C	0.9800	C47—O42	1.301 (14)
N24—H24A	0.8800	O43—H43A	0.8400
N24—H24B	0.8800	C61—C66	1.389 (8)
C261—H26A	0.9800	C61—C62	1.411 (7)
C261—H26B	0.9800	C61—C67	1.493 (8)
C261—H26C	0.9800	C62—O63	1.340 (7)
N51—C56	1.358 (7)	C62—C63	1.392 (7)
N51—C52	1.358 (7)	C63—C64	1.384 (8)
N51—H51A	0.8800	C63—H63	0.9500
C52—N53	1.316 (7)	C64—C65	1.401 (8)
C52—C521	1.499 (7)	C64—H64	0.9500
N53—C54	1.360 (7)	C65—C66	1.377 (7)
C54—N54	1.319 (7)	C65—Cl65	1.757 (6)
C54—C55	1.420 (7)	C66—H66	0.9500
C55—C56	1.364 (7)	C67—O61	1.226 (8)
C55—Cl55	1.733 (6)	C67—O62	1.301 (18)
C56—C561	1.484 (8)	O63—H63A	0.8400
C12—N11—C16	121.3 (3)	H52A—C521—H52B	109.5
C12—N11—H11	119.3	C52—C521—H52C	109.5
C16—N11—H11	119.3	H52A—C521—H52C	109.5
N13—C12—N11	123.0 (3)	H52B—C521—H52C	109.5
N13—C12—C121	120.0 (3)	C54—N54—H54A	120.0
N11—C12—C121	117.0 (3)	C54—N54—H54B	120.0
C12—N13—C14	118.5 (3)	H54A—N54—H54B	120.0
N14—C14—N13	117.1 (3)	C56—C561—H56A	109.5
N14—C14—C15	122.9 (3)	C56—C561—H56B	109.5
N13—C14—C15	120.0 (3)	H56A—C561—H56B	109.5
C16—C15—C14	119.7 (3)	C56—C561—H56C	109.5
C16—C15—Cl15	120.8 (3)	H56A—C561—H56C	109.5
C14—C15—Cl15	119.5 (2)	H56B—C561—H56C	109.5
C15—C16—N11	117.4 (3)	C36—C31—C32	119.2 (3)
C15—C16—C161	124.3 (4)	C36—C31—C37	121.7 (3)
N11—C16—C161	118.2 (3)	C32—C31—C37	119.1 (3)
C12—C121—H12A	109.5	O33—C32—C33	119.5 (3)
C12—C121—H12B	109.5	O33—C32—C31	120.5 (3)
H12A—C121—H12B	109.5	C33—C32—C31	120.0 (3)
C12—C121—H12C	109.5	C34—C33—C32	119.9 (3)
H12A—C121—H12C	109.5	C34—C33—H33	120.1
H12B—C121—H12C	109.5	C32—C33—H33	120.1
C14—N14—H14A	120.0	C33—C34—C35	120.7 (3)
C14—N14—H14B	120.0	C33—C34—H34	119.7
H14A—N14—H14B	120.0	C35—C34—H34	119.7
C16—C161—H16A	109.5	C36—C35—C34	120.0 (3)
C16—C161—H16B	109.5	C36—C35—Cl35	119.6 (3)
H16A—C161—H16B	109.5	C34—C35—Cl35	120.3 (3)
C16—C161—H16C	109.5	C35—C36—C31	120.2 (3)
H16A—C161—H16C	109.5	C35—C36—H36	119.9
H16B—C161—H16C	109.5	C31—C36—H36	119.9
C26—N21—C22	121.6 (3)	O32—C37—O31	125.7 (5)
C26—N21—H21	119.2	O32—C37—C31	118.8 (4)
C22—N21—H21	119.2	O31—C37—C31	115.5 (4)
N23—C22—N21	122.5 (4)	C32—O33—H33A	109.5
N23—C22—C221	119.6 (3)	C46—C41—C42	119.9 (4)
N21—C22—C221	117.8 (3)	C46—C41—C47	118.8 (4)
C22—N23—C24	118.6 (3)	C42—C41—C47	121.3 (4)
N24—C24—N23	117.2 (3)	O43—C42—C43	120.0 (4)
N24—C24—C25	123.0 (4)	O43—C42—C41	120.9 (4)
N23—C24—C25	119.8 (3)	C43—C42—C41	119.1 (4)
C26—C25—C24	120.0 (3)	C44—C43—C42	120.9 (4)
C26—C25—Cl25	120.7 (3)	C44—C43—H43	119.6
C24—C25—Cl25	119.2 (3)	C42—C43—H43	119.6
N21—C26—C25	117.3 (4)	C43—C44—C45	119.2 (4)
N21—C26—C261	117.6 (4)	C43—C44—H44	120.4
C25—C26—C261	125.1 (4)	C45—C44—H44	120.4
C22—C221—H22A	109.5	C46—C45—C44	120.6 (4)
C22—C221—H22B	109.5	C46—C45—Cl45	120.0 (3)
H22A—C221—H22B	109.5	C44—C45—Cl45	119.4 (3)
C22—C221—H22C	109.5	C45—C46—C41	120.3 (4)
H22A—C221—H22C	109.5	C45—C46—H46	119.8
H22B—C221—H22C	109.5	C41—C46—H46	119.8
C24—N24—H24A	120.0	O41—C47—O42	124.5 (7)
C24—N24—H24B	120.0	O41—C47—C41	119.5 (5)
H24A—N24—H24B	120.0	O42—C47—C41	116.0 (6)
C26—C261—H26A	109.5	C42—O43—H43A	109.5
C26—C261—H26B	109.5	C66—C61—C62	118.8 (7)
H26A—C261—H26B	109.5	C66—C61—C67	118.5 (8)
C26—C261—H26C	109.5	C62—C61—C67	119.7 (8)
H26A—C261—H26C	109.5	O63—C62—C63	120.5 (7)
H26B—C261—H26C	109.5	O63—C62—C61	120.1 (7)
C56—N51—C52	121.5 (7)	C63—C62—C61	119.0 (6)
C56—N51—H51A	119.2	C64—C63—C62	120.7 (7)
C52—N51—H51A	119.2	C64—C63—H63	119.6
N53—C52—N51	123.1 (6)	C62—C63—H63	119.6
N53—C52—C521	119.0 (7)	C63—C64—C65	119.2 (7)
N51—C52—C521	117.9 (7)	C63—C64—H64	120.4
C52—N53—C54	118.0 (6)	C65—C64—H64	120.4
N54—C54—N53	116.5 (7)	C66—C65—C64	120.0 (6)
N54—C54—C55	123.8 (7)	C66—C65—Cl65	120.9 (6)
N53—C54—C55	119.8 (6)	C64—C65—Cl65	119.1 (6)
C56—C55—C54	120.5 (6)	C65—C66—C61	120.4 (7)
C56—C55—Cl55	120.2 (6)	C65—C66—H66	119.8
C54—C55—Cl55	119.3 (6)	C61—C66—H66	119.8
N51—C56—C55	116.9 (6)	O61—C67—O62	124.5 (13)
N51—C56—C561	117.0 (8)	O61—C67—C61	119.6 (9)
C55—C56—C561	124.7 (8)	O62—C67—C61	115.7 (8)
C52—C521—H52A	109.5	C62—O63—H63A	109.5
C52—C521—H52B	109.5
C16—N11—C12—N13	0.1 (5)	C36—C31—C32—C33	−0.2 (5)
C16—N11—C12—C121	−179.4 (3)	C37—C31—C32—C33	−179.6 (3)
N11—C12—N13—C14	−1.6 (5)	O33—C32—C33—C34	−179.1 (3)
C121—C12—N13—C14	177.8 (3)	C31—C32—C33—C34	0.8 (5)
C12—N13—C14—N14	−178.7 (3)	C32—C33—C34—C35	−0.8 (5)
C12—N13—C14—C15	1.4 (5)	C33—C34—C35—C36	0.2 (5)
N14—C14—C15—C16	−179.6 (3)	C33—C34—C35—Cl35	−179.8 (3)
N13—C14—C15—C16	0.3 (5)	C34—C35—C36—C31	0.3 (5)
N14—C14—C15—Cl15	−1.8 (5)	Cl35—C35—C36—C31	−179.6 (3)
N13—C14—C15—Cl15	178.1 (3)	C32—C31—C36—C35	−0.3 (5)
C14—C15—C16—N11	−1.7 (5)	C37—C31—C36—C35	179.1 (3)
Cl15—C15—C16—N11	−179.6 (3)	C36—C31—C37—O32	−178.9 (3)
C14—C15—C16—C161	178.1 (3)	C32—C31—C37—O32	0.5 (5)
Cl15—C15—C16—C161	0.2 (5)	C36—C31—C37—O31	1.8 (5)
C12—N11—C16—C15	1.6 (5)	C32—C31—C37—O31	−178.8 (3)
C12—N11—C16—C161	−178.2 (3)	C46—C41—C42—O43	179.9 (4)
C26—N21—C22—N23	1.5 (6)	C47—C41—C42—O43	0.0 (6)
C26—N21—C22—C221	−178.7 (4)	C46—C41—C42—C43	0.2 (6)
N21—C22—N23—C24	−2.6 (6)	C47—C41—C42—C43	−179.6 (4)
C221—C22—N23—C24	177.7 (3)	O43—C42—C43—C44	178.3 (4)
C22—N23—C24—N24	−178.4 (3)	C41—C42—C43—C44	−2.0 (6)
C22—N23—C24—C25	1.7 (5)	C42—C43—C44—C45	2.7 (6)
N24—C24—C25—C26	−179.7 (4)	C43—C44—C45—C46	−1.6 (6)
N23—C24—C25—C26	0.1 (6)	C43—C44—C45—Cl45	179.1 (3)
N24—C24—C25—Cl25	−1.6 (5)	C44—C45—C46—C41	−0.2 (6)
N23—C24—C25—Cl25	178.3 (3)	Cl45—C45—C46—C41	179.1 (3)
C22—N21—C26—C25	0.4 (6)	C42—C41—C46—C45	0.9 (6)
C22—N21—C26—C261	−176.3 (4)	C47—C41—C46—C45	−179.3 (4)
C24—C25—C26—N21	−1.2 (6)	C46—C41—C47—O41	−2.7 (7)
Cl25—C25—C26—N21	−179.3 (3)	C42—C41—C47—O41	177.1 (4)
C24—C25—C26—C261	175.3 (4)	C46—C41—C47—O42	176 (3)
Cl25—C25—C26—C261	−2.9 (6)	C42—C41—C47—O42	−4 (3)
C56—N51—C52—N53	−5 (3)	C66—C61—C62—O63	−174.8 (18)
C56—N51—C52—C521	176.9 (19)	C67—C61—C62—O63	−15 (3)
N51—C52—N53—C54	5 (3)	C66—C61—C62—C63	13 (3)
C521—C52—N53—C54	−177.1 (18)	C67—C61—C62—C63	173 (2)
C52—N53—C54—N54	178.1 (17)	O63—C62—C63—C64	−173.8 (19)
C52—N53—C54—C55	−3 (3)	C61—C62—C63—C64	−2 (3)
N54—C54—C55—C56	−179.5 (19)	C62—C63—C64—C65	−8 (3)
N53—C54—C55—C56	2 (3)	C63—C64—C65—C66	6 (3)
N54—C54—C55—Cl55	2 (3)	C63—C64—C65—Cl65	−174.1 (16)
N53—C54—C55—Cl55	−176.4 (15)	C64—C65—C66—C61	6 (3)
C52—N51—C56—C55	3 (3)	Cl65—C65—C66—C61	−174.4 (15)
C52—N51—C56—C561	170 (2)	C62—C61—C66—C65	−15 (3)
C54—C55—C56—N51	−2 (3)	C67—C61—C66—C65	−175 (2)
Cl55—C55—C56—N51	176.4 (16)	C66—C61—C67—O61	−1 (4)
C54—C55—C56—C561	−167 (2)	C62—C61—C67—O61	−161 (3)
Cl55—C55—C56—C561	11 (3)	C66—C61—C67—O62	−176 (13)
C36—C31—C32—O33	179.7 (3)	C62—C61—C67—O62	24 (14)
C37—C31—C32—O33	0.3 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O41	0.88	1.73	2.597 (6)	166
N14—H14A···N13^i	0.88	2.35	3.180 (4)	156
N14—H14B···O33	0.88	2.10	2.874 (4)	147
O33—H33A···O32	0.84	1.73	2.483 (5)	148
N21—H21···O31	0.88	1.74	2.605 (5)	166
N24—H24A···N23^ii	0.88	2.34	3.163 (5)	156
N24—H24B···O43^iii	0.88	2.11	2.897 (4)	148
O43—H43A···O42	0.84	1.73	2.487 (13)	149

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

2-Amino-4,6-dimethoxypyrimidin-1ium thiophene-2-carboxylate (III)

Crystal data

C6H10N3O2^+·C5H3O2S^−	F(000) = 592
Mr = 283.30	Dx = 1.465 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.7335 (3) Å	Cell parameters from 4262 reflections
b = 7.6307 (4) Å	θ = 3.1–32.7°
c = 25.0638 (10) Å	µ = 0.27 mm^−1
β = 93.928 (4)°	T = 173 K
V = 1284.79 (10) Å^3	Block, colourless
Z = 4	0.32 × 0.28 × 0.14 mm

Data collection

Agilent Eos Gemini diffractometer	4262 independent reflections
Radiation source: fine-focus sealed tube	3087 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 16.0416 pixels mm^-1	θmax = 32.7°, θmin = 3.1°
ω scans	h = −7→9
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012)	k = −11→10
Tmin = 0.752, Tmax = 0.963	l = −36→33
8880 measured reflections

Refinement

Refinement on F^2	18 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.119	w = 1/[σ^2(Fo^2) + (0.0496P)^2 + 0.2546P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
4262 reflections	Δρmax = 0.32 e Å^−3
199 parameters	Δρmin = −0.32 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)
O1	0.32086 (15)	0.14245 (14)	0.38771 (4)	0.0299 (2)
O2	0.23128 (15)	0.13436 (16)	0.57313 (4)	0.0344 (3)
N1	0.53923 (16)	0.26187 (16)	0.44754 (5)	0.0246 (2)
H1	0.6072	0.2925	0.4203	0.030*
N2	0.50876 (17)	0.26067 (16)	0.54142 (5)	0.0255 (2)
N3	0.78320 (18)	0.37857 (19)	0.50524 (5)	0.0347 (3)
H31	0.8323	0.4042	0.5377	0.042*
H32	0.8504	0.4052	0.4775	0.042*
C1	0.6089 (2)	0.30031 (19)	0.49822 (5)	0.0244 (3)
C2	0.3648 (2)	0.17616 (18)	0.43932 (5)	0.0238 (3)
C3	0.2552 (2)	0.13067 (19)	0.48119 (6)	0.0271 (3)
H3	0.1319	0.0705	0.4762	0.033*
C4	0.3372 (2)	0.17884 (19)	0.53174 (6)	0.0256 (3)
C5	0.1469 (2)	0.0368 (2)	0.37448 (6)	0.0355 (4)
H5A	0.1314	0.0194	0.3357	0.053*
H5B	0.0289	0.0963	0.3865	0.053*
H5C	0.1621	−0.0772	0.3923	0.053*
C6	0.3181 (2)	0.1691 (3)	0.62629 (6)	0.0370 (4)
H6A	0.3638	0.2910	0.6285	0.056*
H6B	0.4313	0.0903	0.6341	0.056*
H6C	0.2182	0.1496	0.6523	0.056*
S1A	0.84749 (8)	0.54595 (10)	0.26446 (2)	0.0376 (2)	0.8687 (19)
C1A	1.0432 (3)	0.6531 (4)	0.23815 (9)	0.0400 (5)	0.8687 (19)
H1A	1.0378	0.7023	0.2033	0.048*	0.8687 (19)
C2A	1.2064 (5)	0.6590 (7)	0.27308 (10)	0.0419 (6)	0.8687 (19)
H2A	1.3289	0.7126	0.2658	0.050*	0.8687 (19)
C3A	1.1710 (7)	0.5762 (11)	0.3210 (2)	0.0372 (8)	0.8687 (19)
H3A	1.2695	0.5677	0.3498	0.045*	0.8687 (19)
C4A	0.9862 (5)	0.5089 (8)	0.32334 (11)	0.0262 (4)	0.8687 (19)
C5A	0.8972 (6)	0.4271 (10)	0.36979 (11)	0.0260 (5)	0.8687 (19)
O1A	0.9959 (4)	0.4296 (3)	0.41382 (9)	0.0309 (5)	0.8687 (19)
O2A	0.7246 (5)	0.3595 (8)	0.36208 (12)	0.0364 (6)	0.8687 (19)
S1B	1.2152 (14)	0.568 (2)	0.3275 (5)	0.0372 (8)	0.1313 (19)
C1B	1.184 (3)	0.648 (5)	0.2632 (7)	0.0419 (6)	0.1313 (19)
H1B	1.2887	0.6968	0.2443	0.050*	0.1313 (19)
C2B	0.993 (2)	0.633 (3)	0.2428 (6)	0.0400 (5)	0.1313 (19)
H2B	0.9429	0.6830	0.2098	0.048*	0.1313 (19)
C3B	0.880 (2)	0.536 (3)	0.2766 (6)	0.03757 (17)	0.1313 (19)
H3B	0.7466	0.5030	0.2670	0.045*	0.1313 (19)
C4B	0.975 (3)	0.492 (5)	0.3241 (7)	0.0262 (4)	0.1313 (19)
C5B	0.884 (4)	0.431 (7)	0.3731 (7)	0.0260 (5)	0.1313 (19)
O1B	0.975 (3)	0.466 (3)	0.4169 (7)	0.0309 (5)	0.1313 (19)
O2B	0.707 (4)	0.370 (6)	0.3680 (9)	0.0364 (6)	0.1313 (19)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0302 (5)	0.0367 (6)	0.0230 (5)	−0.0081 (4)	0.0039 (4)	−0.0050 (4)
O2	0.0341 (6)	0.0459 (7)	0.0245 (5)	−0.0043 (5)	0.0112 (4)	0.0020 (5)
N1	0.0265 (5)	0.0272 (6)	0.0205 (5)	−0.0031 (5)	0.0049 (4)	0.0005 (4)
N2	0.0284 (6)	0.0280 (6)	0.0204 (5)	0.0013 (5)	0.0052 (4)	0.0011 (5)
N3	0.0338 (7)	0.0498 (9)	0.0206 (6)	−0.0144 (6)	0.0024 (5)	−0.0009 (5)
C1	0.0283 (7)	0.0241 (7)	0.0211 (6)	0.0006 (5)	0.0037 (5)	0.0010 (5)
C2	0.0260 (6)	0.0227 (7)	0.0231 (6)	−0.0002 (5)	0.0034 (5)	−0.0013 (5)
C3	0.0256 (6)	0.0289 (7)	0.0273 (7)	−0.0029 (5)	0.0054 (5)	0.0012 (6)
C4	0.0287 (7)	0.0248 (7)	0.0241 (6)	0.0039 (5)	0.0082 (5)	0.0029 (5)
C5	0.0341 (8)	0.0396 (9)	0.0327 (8)	−0.0093 (7)	0.0007 (6)	−0.0072 (7)
C6	0.0393 (8)	0.0509 (10)	0.0219 (7)	0.0044 (7)	0.0098 (6)	0.0003 (7)
S1A	0.0422 (3)	0.0527 (3)	0.0175 (3)	0.0001 (2)	−0.00008 (17)	0.0023 (2)
C1A	0.0570 (15)	0.0417 (13)	0.0233 (8)	−0.0003 (11)	0.0172 (9)	0.0070 (7)
C2A	0.0504 (12)	0.0451 (13)	0.0315 (13)	−0.0122 (10)	0.0128 (9)	0.0005 (15)
C3A	0.042 (2)	0.0423 (11)	0.0267 (17)	−0.004 (2)	0.0017 (14)	0.0037 (11)
C4A	0.0327 (8)	0.0277 (15)	0.0185 (6)	0.0002 (6)	0.0036 (5)	0.0004 (6)
C5A	0.0301 (9)	0.0283 (9)	0.0199 (7)	−0.0014 (9)	0.0042 (6)	−0.0009 (8)
O1A	0.0323 (9)	0.0400 (14)	0.0203 (6)	−0.0041 (8)	0.0009 (5)	0.0023 (7)
O2A	0.0352 (9)	0.0538 (13)	0.0205 (10)	−0.0147 (10)	0.0034 (6)	−0.0001 (10)
S1B	0.042 (2)	0.0423 (11)	0.0267 (17)	−0.004 (2)	0.0017 (14)	0.0037 (11)
C1B	0.0504 (12)	0.0451 (13)	0.0315 (13)	−0.0122 (10)	0.0128 (9)	0.0005 (15)
C2B	0.0570 (15)	0.0417 (13)	0.0233 (8)	−0.0003 (11)	0.0172 (9)	0.0070 (7)
C3B	0.0422 (3)	0.0527 (3)	0.0175 (3)	0.0001 (2)	−0.00008 (17)	0.0023 (2)
C4B	0.0327 (8)	0.0277 (15)	0.0185 (6)	0.0002 (6)	0.0036 (5)	0.0004 (6)
C5B	0.0301 (9)	0.0283 (9)	0.0199 (7)	−0.0014 (9)	0.0042 (6)	−0.0009 (8)
O1B	0.0323 (9)	0.0400 (14)	0.0203 (6)	−0.0041 (8)	0.0009 (5)	0.0023 (7)
O2B	0.0352 (9)	0.0538 (13)	0.0205 (10)	−0.0147 (10)	0.0034 (6)	−0.0001 (10)

Geometric parameters (Å, º)

O1—C2	1.3320 (16)	S1A—C1A	1.720 (2)
O1—C5	1.4421 (18)	C1A—C2A	1.358 (3)
O2—C4	1.3423 (15)	C1A—H1A	0.9500
O2—C6	1.4424 (19)	C2A—C3A	1.391 (6)
N1—C2	1.3479 (17)	C2A—H2A	0.9500
N1—C1	1.3558 (17)	C3A—C4A	1.352 (5)
N1—H1	0.8803	C3A—H3A	0.9500
N2—C4	1.3208 (19)	C4A—C5A	1.483 (2)
N2—C1	1.3484 (16)	C5A—O1A	1.249 (2)
N3—C1	1.3179 (18)	C5A—O2A	1.2742 (19)
N3—H31	0.8790	S1B—C4B	1.716 (6)
N3—H32	0.8788	S1B—C1B	1.721 (5)
C2—C3	1.3681 (18)	C1B—C2B	1.358 (5)
C3—C4	1.396 (2)	C1B—H1B	0.9500
C3—H3	0.9500	C2B—C3B	1.389 (7)
C5—H5A	0.9800	C2B—H2B	0.9500
C5—H5B	0.9800	C3B—C4B	1.353 (7)
C5—H5C	0.9800	C3B—H3B	0.9500
C6—H6A	0.9800	C4B—C5B	1.485 (5)
C6—H6B	0.9800	C5B—O1B	1.249 (5)
C6—H6C	0.9800	C5B—O2B	1.274 (5)
S1A—C4A	1.715 (2)
C2—O1—C5	117.00 (11)	C4A—S1A—C1A	91.26 (11)
C4—O2—C6	117.66 (12)	C2A—C1A—S1A	112.08 (17)
C2—N1—C1	119.36 (11)	C2A—C1A—H1A	124.0
C2—N1—H1	120.3	S1A—C1A—H1A	124.0
C1—N1—H1	120.4	C1A—C2A—C3A	111.2 (2)
C4—N2—C1	115.96 (12)	C1A—C2A—H2A	124.4
C1—N3—H31	120.0	C3A—C2A—H2A	124.4
C1—N3—H32	120.1	C4A—C3A—C2A	115.1 (3)
H31—N3—H32	120.0	C4A—C3A—H3A	122.5
N3—C1—N2	118.96 (13)	C2A—C3A—H3A	122.5
N3—C1—N1	118.10 (12)	C3A—C4A—C5A	128.1 (3)
N2—C1—N1	122.94 (13)	C3A—C4A—S1A	110.4 (2)
O1—C2—N1	112.05 (11)	C5A—C4A—S1A	121.30 (17)
O1—C2—C3	126.90 (13)	O1A—C5A—O2A	124.4 (2)
N1—C2—C3	121.05 (13)	O1A—C5A—C4A	117.93 (16)
C2—C3—C4	115.39 (13)	O2A—C5A—C4A	117.69 (18)
C2—C3—H3	122.3	C4B—S1B—C1B	91.1 (4)
C4—C3—H3	122.3	C2B—C1B—S1B	112.0 (5)
N2—C4—O2	118.81 (13)	C2B—C1B—H1B	124.0
N2—C4—C3	125.28 (12)	S1B—C1B—H1B	124.0
O2—C4—C3	115.90 (13)	C1B—C2B—C3B	111.0 (6)
O1—C5—H5A	109.5	C1B—C2B—H2B	124.5
O1—C5—H5B	109.5	C3B—C2B—H2B	124.5
H5A—C5—H5B	109.5	C4B—C3B—C2B	115.1 (6)
O1—C5—H5C	109.5	C4B—C3B—H3B	122.4
H5A—C5—H5C	109.5	C2B—C3B—H3B	122.4
H5B—C5—H5C	109.5	C3B—C4B—C5B	127.6 (10)
O2—C6—H6A	109.5	C3B—C4B—S1B	110.2 (5)
O2—C6—H6B	109.5	C5B—C4B—S1B	120.4 (7)
H6A—C6—H6B	109.5	O1B—C5B—O2B	124.3 (10)
O2—C6—H6C	109.5	O1B—C5B—C4B	117.1 (7)
H6A—C6—H6C	109.5	O2B—C5B—C4B	117.8 (7)
H6B—C6—H6C	109.5
C4—N2—C1—N3	−178.52 (14)	C2A—C3A—C4A—C5A	−174.4 (6)
C4—N2—C1—N1	0.9 (2)	C2A—C3A—C4A—S1A	0.4 (9)
C2—N1—C1—N3	177.61 (13)	C1A—S1A—C4A—C3A	−0.3 (5)
C2—N1—C1—N2	−1.8 (2)	C1A—S1A—C4A—C5A	174.9 (4)
C5—O1—C2—N1	174.35 (13)	C3A—C4A—C5A—O1A	5.7 (9)
C5—O1—C2—C3	−4.5 (2)	S1A—C4A—C5A—O1A	−168.6 (6)
C1—N1—C2—O1	−177.61 (12)	C3A—C4A—C5A—O2A	−174.6 (9)
C1—N1—C2—C3	1.4 (2)	S1A—C4A—C5A—O2A	11.1 (8)
O1—C2—C3—C4	178.68 (14)	C4B—S1B—C1B—C2B	6 (3)
N1—C2—C3—C4	−0.1 (2)	S1B—C1B—C2B—C3B	−8 (4)
C1—N2—C4—O2	179.40 (13)	C1B—C2B—C3B—C4B	6 (4)
C1—N2—C4—C3	0.5 (2)	C2B—C3B—C4B—C5B	163 (3)
C6—O2—C4—N2	−3.9 (2)	C2B—C3B—C4B—S1B	−2 (4)
C6—O2—C4—C3	175.14 (13)	C1B—S1B—C4B—C3B	−3 (3)
C2—C3—C4—N2	−0.8 (2)	C1B—S1B—C4B—C5B	−168 (3)
C2—C3—C4—O2	−179.79 (13)	C3B—C4B—C5B—O1B	−151 (5)
C4A—S1A—C1A—C2A	0.2 (4)	S1B—C4B—C5B—O1B	12 (5)
S1A—C1A—C2A—C3A	0.0 (6)	C3B—C4B—C5B—O2B	19 (6)
C1A—C2A—C3A—C4A	−0.3 (9)	S1B—C4B—C5B—O2B	−178 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2A	0.88	1.78	2.658 (4)	175
N3—H31···O1A^i	0.88	2.06	2.839 (3)	148
N3—H32···O1A	0.88	1.94	2.811 (3)	172
N1—H1···O2B	0.88	1.62	2.50 (3)	172
N3—H31···O1B^i	0.88	1.94	2.73 (2)	148
N3—H32···O1B	0.88	1.84	2.722 (19)	176

Symmetry code: (i) −x+2, −y+1, −z+1.