Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
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\overline{1}, 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).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617013481/yf3127sup1.cif
Contains datablocks global, I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617013481/yf3127Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617013481/yf3127Isup5.cml
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617013481/yf3127IIsup3.hkl
Contains datablock II

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617013481/yf3127IIsup6.cml
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617013481/yf3127IIIsup4.hkl
Contains datablock III

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617013481/yf3127IIIsup7.cml
Supplementary material

CCDC references: 1405154; 1575633; 1575632

Computing details top

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) top
Crystal data top
C6H9ClN3+·C7H4ClO3Z = 4
Mr = 330.16F(000) = 680
Triclinic, P1Dx = 1.532 Mg m3
a = 9.3874 (4) ÅCu Kα radiation, λ = 1.54178 Å
b = 10.5102 (4) ÅCell parameters from 4963 reflections
c = 15.4295 (6) Åθ = 3.0–66.6°
α = 71.167 (1)°µ = 4.22 mm1
β = 83.335 (2)°T = 100 K
γ = 87.730 (1)°Needle, colourless
V = 1431.09 (10) Å30.24 × 0.07 × 0.05 mm
Data collection top
Bruker APEXII CCD
diffractometer
4962 independent reflections
Radiation source: fine-focus sealed tube4460 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ω scansθmax = 66.6°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1111
Tmin = 0.654, Tmax = 0.810k = 1210
18796 measured reflectionsl = 1818
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.081 w = 1/[σ2(Fo2) + (0.0284P)2 + 1.245P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
4962 reflectionsΔρmax = 0.34 e Å3
407 parametersΔρmin = 0.26 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
N111.02592 (16)0.52970 (15)0.12086 (10)0.0201 (3)
C120.89213 (19)0.56943 (18)0.12706 (12)0.0190 (4)
N130.80979 (16)0.54908 (15)0.20861 (10)0.0184 (3)
H130.709 (2)0.579 (2)0.2083 (14)0.022*
C140.86161 (19)0.48424 (18)0.29006 (12)0.0188 (4)
C151.00531 (19)0.44032 (18)0.28493 (12)0.0190 (4)
Cl151.07360 (5)0.35441 (5)0.38717 (3)0.02719 (12)
C161.08401 (19)0.46291 (18)0.20063 (12)0.0189 (4)
C1210.8235 (2)0.6413 (2)0.04175 (12)0.0241 (4)
H12A0.85820.60300.00690.036*
H12B0.84820.73700.02150.036*
H12C0.71910.63120.05480.036*
N140.77572 (18)0.46578 (17)0.36681 (11)0.0228 (3)
H14B0.684 (3)0.493 (2)0.3633 (15)0.027*
H14A0.809 (2)0.425 (2)0.4170 (16)0.027*
C1611.2341 (2)0.4139 (2)0.18923 (14)0.0249 (4)
H16A1.28720.47730.13510.037*
H16B1.23280.32540.18080.037*
H16C1.28080.40670.24420.037*
N210.33481 (17)0.14191 (16)0.71858 (11)0.0242 (3)
C220.3861 (2)0.16006 (19)0.63259 (13)0.0232 (4)
N230.51357 (16)0.10973 (16)0.60814 (11)0.0221 (3)
H230.543 (2)0.128 (2)0.5403 (16)0.027*
C240.5991 (2)0.03751 (18)0.67171 (13)0.0221 (4)
C250.5464 (2)0.01743 (18)0.76476 (13)0.0220 (4)
Cl250.65260 (5)0.07187 (5)0.84854 (3)0.02810 (12)
C260.4159 (2)0.06952 (19)0.78613 (13)0.0230 (4)
C2210.3027 (2)0.2381 (2)0.55594 (14)0.0304 (5)
H22A0.24060.30290.57580.046*
H22B0.24380.17650.53930.046*
H22C0.36900.28610.50240.046*
N240.72276 (18)0.00753 (18)0.64309 (13)0.0276 (4)
H24B0.751 (3)0.016 (2)0.5802 (18)0.033*
H24A0.780 (3)0.043 (2)0.6811 (17)0.033*
C2610.3559 (2)0.0530 (2)0.88334 (14)0.0292 (4)
H26A0.36800.04050.92180.044*
H26B0.25360.07600.88520.044*
H26C0.40670.11270.90670.044*
C310.31187 (19)0.67355 (18)0.27484 (12)0.0182 (4)
C320.2223 (2)0.66823 (19)0.35563 (12)0.0210 (4)
C330.0865 (2)0.7266 (2)0.34955 (13)0.0247 (4)
H330.02600.72180.40430.030*
C340.0386 (2)0.79131 (19)0.26498 (13)0.0234 (4)
H340.05430.83070.26110.028*
C350.1290 (2)0.79779 (18)0.18564 (12)0.0201 (4)
Cl350.07191 (5)0.88579 (5)0.07862 (3)0.02524 (12)
C360.26328 (19)0.73941 (17)0.18960 (12)0.0185 (4)
H360.32250.74410.13440.022*
C370.45865 (19)0.61226 (18)0.27996 (13)0.0207 (4)
O310.53626 (13)0.62162 (14)0.20630 (9)0.0237 (3)
O320.49630 (14)0.55505 (14)0.36027 (9)0.0277 (3)
O330.26546 (15)0.60848 (15)0.44005 (9)0.0278 (3)
H33A0.358 (3)0.577 (2)0.4305 (17)0.042*
C410.7494 (2)0.17511 (19)0.30036 (13)0.0233 (4)
C420.8866 (2)0.1437 (2)0.26513 (14)0.0253 (4)
C430.9240 (2)0.1812 (2)0.17049 (14)0.0279 (4)
H431.01630.15880.14710.033*
C440.8285 (2)0.2506 (2)0.11015 (14)0.0275 (4)
H440.85510.27720.04550.033*
C450.6931 (2)0.28109 (19)0.14496 (14)0.0255 (4)
Cl450.57379 (5)0.36671 (5)0.06714 (3)0.03388 (13)
C460.6530 (2)0.24430 (18)0.23872 (14)0.0240 (4)
H460.55990.26600.26130.029*
C470.7070 (2)0.13490 (19)0.40214 (14)0.0254 (4)
O410.58295 (14)0.16233 (14)0.43069 (9)0.0283 (3)
O420.80090 (15)0.07389 (15)0.45412 (10)0.0339 (3)
O430.98479 (15)0.07879 (15)0.32111 (10)0.0327 (3)
H43A0.942 (3)0.066 (3)0.3819 (19)0.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0176 (8)0.0250 (8)0.0203 (8)0.0017 (6)0.0017 (6)0.0122 (6)
C120.0202 (9)0.0223 (9)0.0172 (9)0.0038 (7)0.0014 (7)0.0110 (7)
N130.0142 (8)0.0253 (8)0.0174 (8)0.0006 (6)0.0005 (6)0.0097 (6)
C140.0198 (9)0.0203 (9)0.0179 (9)0.0030 (7)0.0002 (7)0.0088 (7)
C150.0185 (9)0.0190 (9)0.0206 (9)0.0004 (7)0.0024 (7)0.0076 (7)
Cl150.0249 (2)0.0310 (3)0.0225 (2)0.00505 (18)0.00374 (18)0.00438 (19)
C160.0176 (9)0.0182 (9)0.0241 (10)0.0025 (7)0.0010 (7)0.0121 (7)
C1210.0183 (9)0.0376 (11)0.0174 (9)0.0003 (8)0.0008 (7)0.0113 (8)
N140.0183 (8)0.0320 (9)0.0163 (8)0.0012 (7)0.0008 (6)0.0065 (7)
C1610.0205 (10)0.0280 (10)0.0286 (10)0.0038 (8)0.0004 (8)0.0138 (8)
N210.0204 (8)0.0258 (9)0.0277 (9)0.0009 (6)0.0021 (7)0.0123 (7)
C220.0202 (9)0.0224 (10)0.0293 (10)0.0007 (7)0.0016 (8)0.0128 (8)
N230.0199 (8)0.0236 (8)0.0239 (9)0.0004 (6)0.0022 (6)0.0108 (7)
C240.0194 (9)0.0190 (9)0.0299 (10)0.0038 (7)0.0011 (8)0.0114 (8)
C250.0211 (9)0.0179 (9)0.0275 (10)0.0030 (7)0.0005 (8)0.0083 (8)
Cl250.0285 (3)0.0252 (2)0.0290 (3)0.00219 (18)0.00214 (19)0.00696 (19)
C260.0220 (10)0.0205 (9)0.0280 (10)0.0051 (7)0.0030 (8)0.0111 (8)
C2210.0247 (10)0.0368 (12)0.0316 (11)0.0083 (9)0.0017 (9)0.0150 (9)
N240.0206 (9)0.0348 (10)0.0284 (10)0.0049 (7)0.0002 (7)0.0128 (8)
C2610.0291 (11)0.0314 (11)0.0259 (11)0.0003 (8)0.0055 (8)0.0103 (9)
C310.0174 (9)0.0188 (9)0.0195 (9)0.0040 (7)0.0016 (7)0.0084 (7)
C320.0212 (9)0.0242 (10)0.0175 (9)0.0033 (7)0.0004 (7)0.0069 (7)
C330.0225 (10)0.0317 (11)0.0192 (9)0.0027 (8)0.0046 (7)0.0101 (8)
C340.0204 (9)0.0247 (10)0.0259 (10)0.0040 (7)0.0000 (8)0.0109 (8)
C350.0228 (9)0.0193 (9)0.0186 (9)0.0007 (7)0.0027 (7)0.0066 (7)
Cl350.0268 (2)0.0273 (2)0.0198 (2)0.00532 (18)0.00396 (18)0.00508 (18)
C360.0190 (9)0.0203 (9)0.0173 (9)0.0034 (7)0.0019 (7)0.0086 (7)
C370.0174 (9)0.0235 (10)0.0214 (10)0.0041 (7)0.0005 (7)0.0081 (8)
O310.0169 (6)0.0360 (8)0.0186 (7)0.0007 (5)0.0013 (5)0.0103 (6)
O320.0195 (7)0.0404 (8)0.0191 (7)0.0031 (6)0.0004 (5)0.0048 (6)
O330.0218 (7)0.0433 (8)0.0160 (7)0.0045 (6)0.0002 (5)0.0078 (6)
C410.0223 (10)0.0201 (9)0.0295 (10)0.0048 (7)0.0067 (8)0.0133 (8)
C420.0215 (10)0.0258 (10)0.0326 (11)0.0009 (8)0.0017 (8)0.0164 (8)
C430.0205 (10)0.0336 (11)0.0335 (11)0.0027 (8)0.0071 (8)0.0194 (9)
C440.0269 (10)0.0306 (11)0.0277 (10)0.0074 (8)0.0073 (8)0.0156 (9)
C450.0263 (10)0.0215 (10)0.0288 (10)0.0048 (8)0.0018 (8)0.0094 (8)
Cl450.0268 (3)0.0377 (3)0.0317 (3)0.0000 (2)0.0032 (2)0.0058 (2)
C460.0202 (9)0.0197 (9)0.0329 (11)0.0023 (7)0.0065 (8)0.0125 (8)
C470.0237 (10)0.0236 (10)0.0305 (11)0.0035 (8)0.0050 (8)0.0130 (8)
O410.0230 (7)0.0333 (8)0.0274 (7)0.0007 (6)0.0069 (6)0.0113 (6)
O420.0274 (8)0.0432 (9)0.0295 (8)0.0069 (6)0.0033 (6)0.0124 (7)
O430.0242 (7)0.0437 (9)0.0318 (8)0.0070 (6)0.0020 (6)0.0168 (7)
Geometric parameters (Å, º) top
N11—C121.310 (2)C221—H22C0.9800
C12—N131.357 (2)N24—H24B0.93 (3)
C12—C1211.495 (3)N24—H24A0.83 (2)
N13—C141.358 (2)C261—H26A0.9800
N13—H130.99 (2)C261—H26B0.9800
C14—C151.410 (3)C261—H26C0.9800
C15—C161.373 (3)C31—C361.394 (3)
C16—N111.368 (2)C31—C321.407 (2)
C14—N141.316 (2)C31—C371.497 (3)
C15—Cl151.7274 (18)C32—O331.353 (2)
C16—C1611.491 (3)C32—C331.392 (3)
C121—H12A0.9800C33—C341.381 (3)
C121—H12B0.9800C33—H330.9500
C121—H12C0.9800C34—C351.390 (3)
N14—H14B0.90 (2)C34—H340.9500
N14—H14A0.84 (2)C35—C361.379 (3)
C161—H16A0.9800C35—Cl351.7462 (18)
C161—H16B0.9800C36—H360.9500
C161—H16C0.9800O33—H33A0.93 (3)
C37—O311.254 (2)C41—C461.398 (3)
C37—O321.275 (2)C41—C421.408 (3)
N21—C221.313 (3)C41—C471.498 (3)
C22—N231.352 (2)C42—O431.348 (2)
C22—C2211.490 (3)C42—C431.390 (3)
N23—C241.355 (3)C43—C441.381 (3)
N23—H231.01 (2)C43—H430.9500
C24—C251.414 (3)C44—C451.388 (3)
C25—C261.371 (3)C44—H440.9500
C25—Cl251.7284 (19)C45—C461.381 (3)
C26—N211.368 (3)C45—Cl451.743 (2)
C24—N241.319 (3)C46—H460.9500
C26—C2611.497 (3)C47—O411.253 (2)
C221—H22A0.9800C47—O421.272 (2)
C221—H22B0.9800O43—H43A0.95 (3)
C12—N11—C16118.13 (15)C24—N24—H24B119.2 (15)
N11—C12—N13123.10 (17)C24—N24—H24A118.8 (17)
N11—C12—C121120.06 (16)H24B—N24—H24A121 (2)
N13—C12—C121116.84 (16)C26—C261—H26A109.5
C12—N13—C14121.51 (16)C26—C261—H26B109.5
C12—N13—H13118.9 (12)H26A—C261—H26B109.5
C14—N13—H13119.5 (12)C26—C261—H26C109.5
N14—C14—N13118.63 (17)H26A—C261—H26C109.5
N14—C14—C15125.05 (17)H26B—C261—H26C109.5
N13—C14—C15116.31 (16)C36—C31—C32119.03 (17)
C16—C15—C14119.94 (17)C36—C31—C37120.27 (16)
C16—C15—Cl15122.50 (14)C32—C31—C37120.68 (16)
C14—C15—Cl15117.53 (14)O33—C32—C33118.64 (16)
N11—C16—C15121.00 (16)O33—C32—C31121.46 (17)
N11—C16—C161115.80 (16)C33—C32—C31119.89 (17)
C15—C16—C161123.17 (17)C34—C33—C32120.89 (17)
C12—C121—H12A109.5C34—C33—H33119.6
C12—C121—H12B109.5C32—C33—H33119.6
H12A—C121—H12B109.5C33—C34—C35118.70 (17)
C12—C121—H12C109.5C33—C34—H34120.6
H12A—C121—H12C109.5C35—C34—H34120.6
H12B—C121—H12C109.5C36—C35—C34121.66 (17)
C14—N14—H14B118.9 (14)C36—C35—Cl35119.47 (14)
C14—N14—H14A117.9 (15)C34—C35—Cl35118.86 (14)
H14B—N14—H14A123 (2)C35—C36—C31119.82 (16)
C16—C161—H16A109.5C35—C36—H36120.1
C16—C161—H16B109.5C31—C36—H36120.1
H16A—C161—H16B109.5O31—C37—O32124.59 (17)
C16—C161—H16C109.5O31—C37—C31118.68 (16)
H16A—C161—H16C109.5O32—C37—C31116.73 (16)
H16B—C161—H16C109.5C32—O33—H33A106.5 (15)
C22—N21—C26117.86 (16)C46—C41—C42118.90 (18)
N21—C22—N23123.21 (18)C46—C41—C47120.39 (17)
N21—C22—C221120.37 (17)C42—C41—C47120.71 (18)
N23—C22—C221116.42 (17)O43—C42—C43118.41 (17)
C22—N23—C24121.81 (17)O43—C42—C41121.61 (18)
C22—N23—H23117.2 (12)C43—C42—C41119.98 (19)
C24—N23—H23121.0 (12)C44—C43—C42120.70 (18)
N24—C24—N23118.67 (18)C44—C43—H43119.6
N24—C24—C25125.39 (19)C42—C43—H43119.6
N23—C24—C25115.94 (16)C43—C44—C45119.27 (18)
C26—C25—C24120.10 (18)C43—C44—H44120.4
C26—C25—Cl25122.09 (15)C45—C44—H44120.4
C24—C25—Cl25117.80 (14)C46—C45—C44121.13 (19)
N21—C26—C25121.08 (17)C46—C45—Cl45120.59 (15)
N21—C26—C261116.56 (16)C44—C45—Cl45118.28 (16)
C25—C26—C261122.36 (18)C45—C46—C41120.01 (17)
C22—C221—H22A109.5C45—C46—H46120.0
C22—C221—H22B109.5C41—C46—H46120.0
H22A—C221—H22B109.5O41—C47—O42124.30 (18)
C22—C221—H22C109.5O41—C47—C41118.74 (18)
H22A—C221—H22C109.5O42—C47—C41116.97 (17)
H22B—C221—H22C109.5C42—O43—H43A105.9 (16)
C16—N11—C12—N131.0 (3)C37—C31—C32—O330.2 (3)
C16—N11—C12—C121179.28 (16)C36—C31—C32—C330.9 (3)
N11—C12—N13—C140.6 (3)C37—C31—C32—C33179.55 (17)
C121—C12—N13—C14179.67 (16)O33—C32—C33—C34178.59 (17)
C12—N13—C14—N14178.96 (16)C31—C32—C33—C340.7 (3)
C12—N13—C14—C150.4 (2)C32—C33—C34—C350.3 (3)
N14—C14—C15—C16178.65 (17)C33—C34—C35—C361.1 (3)
N13—C14—C15—C160.6 (2)C33—C34—C35—Cl35177.27 (14)
N14—C14—C15—Cl150.6 (3)C34—C35—C36—C310.9 (3)
N13—C14—C15—Cl15178.70 (12)Cl35—C35—C36—C31177.47 (13)
C12—N11—C16—C151.2 (2)C32—C31—C36—C350.1 (3)
C12—N11—C16—C161176.96 (16)C37—C31—C36—C35178.74 (16)
C14—C15—C16—N111.1 (3)C36—C31—C37—O310.1 (3)
Cl15—C15—C16—N11179.05 (13)C32—C31—C37—O31178.54 (16)
C14—C15—C16—C161176.96 (17)C36—C31—C37—O32179.22 (16)
Cl15—C15—C16—C1611.0 (3)C32—C31—C37—O320.6 (3)
C26—N21—C22—N230.7 (3)C46—C41—C42—O43179.08 (17)
C26—N21—C22—C221179.99 (17)C47—C41—C42—O431.1 (3)
N21—C22—N23—C240.9 (3)C46—C41—C42—C430.1 (3)
C221—C22—N23—C24179.77 (17)C47—C41—C42—C43179.69 (17)
C22—N23—C24—N24179.35 (17)O43—C42—C43—C44178.50 (17)
C22—N23—C24—C250.4 (3)C41—C42—C43—C440.7 (3)
N24—C24—C25—C26179.88 (18)C42—C43—C44—C451.0 (3)
N23—C24—C25—C260.1 (3)C43—C44—C45—C460.6 (3)
N24—C24—C25—Cl250.7 (3)C43—C44—C45—Cl45179.10 (15)
N23—C24—C25—Cl25179.04 (13)C44—C45—C46—C410.0 (3)
C22—N21—C26—C250.1 (3)Cl45—C45—C46—C41179.69 (14)
C22—N21—C26—C261178.79 (17)C42—C41—C46—C450.2 (3)
C24—C25—C26—N210.3 (3)C47—C41—C46—C45179.95 (17)
Cl25—C25—C26—N21178.83 (13)C46—C41—C47—O411.3 (3)
C24—C25—C26—C261179.11 (17)C42—C41—C47—O41178.55 (17)
Cl25—C25—C26—C2610.0 (3)C46—C41—C47—O42179.02 (17)
C36—C31—C32—O33178.37 (16)C42—C41—C47—O421.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N13—H13···O310.985 (19)1.666 (19)2.650 (2)177 (2)
N14—H14A···O33i0.84 (2)2.15 (2)2.810 (2)134.4 (18)
N14—H14B···O320.90 (3)1.86 (3)2.753 (2)176.7 (15)
O33—H33A···O320.93 (3)1.65 (3)2.502 (2)150 (2)
N23—H23···O411.01 (2)1.61 (2)2.620 (2)177.0 (17)
N24—H24A···O43ii0.83 (3)2.22 (3)2.885 (2)137 (2)
N24—H24B···O420.93 (3)1.85 (3)2.777 (2)176 (2)
O43—H43A···O420.95 (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) top
Crystal data top
C6H9ClN3+·C7H4ClO3F(000) = 1360
Mr = 330.16Dx = 1.510 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 24.7483 (12) ÅCell parameters from 5117 reflections
b = 6.9525 (3) Åθ = 1.9–66.9°
c = 18.1423 (8) ŵ = 4.16 mm1
β = 111.500 (3)°T = 100 K
V = 2904.4 (2) Å3Block, colourless
Z = 80.10 × 0.04 × 0.04 mm
Data collection top
Rigaku Oxford Diffration Gemini
diffractometer
5116 independent reflections
Radiation source: fine-focus sealed tube4647 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
ω scansθmax = 66.9°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 2829
Tmin = 0.683, Tmax = 0.847k = 88
19622 measured reflectionsl = 2121
Refinement top
Refinement on F250 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.104 w = 1/[σ2(Fo2) + (0.0624P)2 + 1.794P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.043
5116 reflectionsΔρmax = 0.51 e Å3
454 parametersΔρmin = 0.40 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
N110.67190 (12)0.3050 (4)0.61584 (17)0.0126 (5)
H110.70670.28390.61480.015*
C120.62749 (15)0.3456 (4)0.5477 (2)0.0131 (6)
N130.57455 (12)0.3790 (4)0.54442 (16)0.0140 (5)
C140.56348 (14)0.3675 (5)0.6130 (2)0.0139 (6)
C150.60904 (14)0.3248 (4)0.68556 (19)0.0130 (6)
Cl150.59493 (4)0.31775 (13)0.77160 (5)0.0182 (2)
C160.66393 (16)0.2960 (5)0.6869 (2)0.0143 (7)
C1210.64070 (15)0.3500 (5)0.4738 (2)0.0162 (7)
H12A0.60470.36960.42810.024*
H12B0.65840.22760.46800.024*
H12C0.66770.45550.47690.024*
N140.50929 (11)0.3982 (4)0.60751 (17)0.0172 (6)
H14A0.48230.42450.56120.021*
H14B0.50030.39220.65010.021*
C1610.7158 (2)0.2559 (4)0.7604 (3)0.0143 (9)
H16A0.70640.15290.79070.021*
H16B0.72630.37260.79290.021*
H16C0.74850.21600.74570.021*
N210.17238 (13)0.1844 (5)0.5546 (2)0.0158 (7)0.836 (2)
H210.20750.20140.59020.019*0.836 (2)
C220.12770 (15)0.1485 (5)0.5792 (2)0.0136 (8)0.836 (2)
N230.07439 (13)0.1174 (5)0.52944 (19)0.0152 (7)0.836 (2)
C240.06323 (15)0.1288 (5)0.4504 (2)0.0144 (8)0.836 (2)
C250.10910 (18)0.1684 (5)0.4233 (2)0.0153 (8)0.836 (2)
Cl250.09450 (4)0.17614 (15)0.32246 (5)0.0200 (3)0.836 (2)
C260.16424 (17)0.1945 (6)0.4765 (2)0.0145 (8)0.836 (2)
C2210.14065 (17)0.1442 (6)0.6665 (2)0.0206 (9)0.836 (2)
H22A0.10420.14450.67600.031*0.836 (2)
H22B0.16360.25770.69130.031*0.836 (2)
H22C0.16270.02750.68920.031*0.836 (2)
N240.00906 (13)0.1014 (5)0.40204 (19)0.0202 (7)0.836 (2)
H24A0.01800.07690.42140.024*0.836 (2)
H24B0.00000.10750.35050.024*0.836 (2)
C2610.2162 (2)0.2223 (6)0.4556 (4)0.0190 (15)0.836 (2)
H26A0.20990.33180.41940.028*0.836 (2)
H26B0.22310.10600.42980.028*0.836 (2)
H26C0.25010.24750.50390.028*0.836 (2)
N510.1719 (4)0.304 (3)0.5545 (5)0.0158 (7)0.164 (2)
H51A0.20700.28730.59020.019*0.164 (2)
C520.1274 (4)0.345 (3)0.5787 (5)0.0136 (8)0.164 (2)
N530.0745 (4)0.384 (2)0.5294 (5)0.0152 (7)0.164 (2)
C540.0633 (4)0.370 (3)0.4503 (5)0.0144 (8)0.164 (2)
C550.1089 (4)0.323 (3)0.4236 (4)0.0153 (8)0.164 (2)
Cl550.0950 (2)0.3186 (8)0.3228 (2)0.0200 (3)0.164 (2)
C560.1635 (4)0.287 (3)0.4765 (5)0.0145 (8)0.164 (2)
C5210.1401 (6)0.350 (3)0.6661 (5)0.0206 (9)0.164 (2)
H52A0.13740.48310.68250.031*0.164 (2)
H52B0.17930.30100.69470.031*0.164 (2)
H52C0.11180.27030.67820.031*0.164 (2)
N540.0095 (4)0.405 (2)0.4026 (7)0.0202 (7)0.164 (2)
H54A0.01690.43550.42240.024*0.164 (2)
H54B0.00000.39760.35090.024*0.164 (2)
C5610.2162 (6)0.275 (5)0.4560 (10)0.0190 (15)0.164 (2)
H56A0.24100.16960.48590.028*0.164 (2)
H56B0.23770.39630.46950.028*0.164 (2)
H56C0.20480.25030.39910.028*0.164 (2)
C310.36550 (15)0.3020 (5)0.7575 (2)0.0141 (7)
C320.42308 (15)0.3326 (4)0.7633 (2)0.0159 (7)
C330.46632 (15)0.3692 (5)0.8368 (2)0.0196 (7)
H330.50510.39140.84060.024*
C340.45269 (16)0.3729 (5)0.9038 (2)0.0196 (7)
H340.48240.39630.95390.024*
C350.39593 (16)0.3429 (4)0.8989 (2)0.0167 (7)
Cl350.37899 (4)0.34859 (12)0.98413 (5)0.0235 (2)
C360.35252 (16)0.3081 (5)0.8261 (2)0.0156 (7)
H360.31370.28830.82290.019*
C370.3194 (2)0.2614 (4)0.6772 (3)0.0140 (9)
O310.26786 (15)0.2385 (4)0.6765 (2)0.0233 (8)
O320.33368 (17)0.2549 (4)0.6187 (2)0.0264 (9)
O330.43709 (11)0.3267 (4)0.69768 (15)0.0219 (5)
H33A0.40780.29360.65850.033*
C410.86524 (17)0.3106 (6)0.6068 (2)0.0146 (8)0.834 (2)
C420.92287 (17)0.3364 (5)0.6592 (2)0.0187 (8)0.834 (2)
C430.96595 (17)0.3699 (6)0.6284 (3)0.0243 (9)0.834 (2)
H431.00480.39160.66350.029*0.834 (2)
C440.95295 (18)0.3719 (6)0.5474 (3)0.0225 (9)0.834 (2)
H440.98280.38930.52690.027*0.834 (2)
C450.89526 (19)0.3479 (6)0.4962 (2)0.0195 (9)0.834 (2)
Cl450.87834 (5)0.35384 (15)0.39354 (6)0.0265 (3)0.834 (2)
C460.85207 (18)0.3180 (6)0.5257 (2)0.0168 (8)0.834 (2)
H460.81300.30230.49040.020*0.834 (2)
C470.8174 (2)0.2757 (7)0.6366 (3)0.0159 (15)0.834 (2)
O410.76736 (17)0.2615 (6)0.5892 (3)0.0190 (12)0.834 (2)
O420.8328 (3)0.260 (8)0.7130 (5)0.0244 (10)0.834 (2)
O430.93656 (13)0.3302 (5)0.73796 (17)0.0235 (7)0.834 (2)
H43A0.90660.30600.74780.035*0.834 (2)
C610.8666 (4)0.211 (3)0.6092 (5)0.0146 (8)0.166 (2)
C620.9230 (5)0.161 (3)0.6612 (5)0.0187 (8)0.166 (2)
C630.9659 (5)0.128 (3)0.6300 (5)0.0243 (9)0.166 (2)
H631.00420.09730.66460.029*0.166 (2)
C640.9533 (4)0.138 (3)0.5492 (5)0.0225 (9)0.166 (2)
H640.98350.13080.52880.027*0.166 (2)
C650.8954 (4)0.159 (3)0.4979 (4)0.0195 (9)0.166 (2)
Cl650.8788 (2)0.1496 (7)0.3952 (3)0.0265 (3)0.166 (2)
C660.8525 (4)0.187 (3)0.5283 (5)0.0168 (8)0.166 (2)
H660.81290.18990.49360.020*0.166 (2)
C670.8185 (6)0.225 (5)0.6400 (9)0.0140 (9)0.166 (2)
O610.7680 (5)0.218 (5)0.5937 (14)0.0190 (12)0.166 (2)
O620.8343 (12)0.26 (4)0.715 (2)0.0244 (10)0.166 (2)
O630.9365 (5)0.169 (2)0.7397 (5)0.0235 (7)0.166 (2)
H63A0.90830.12860.75060.035*0.166 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.0130 (13)0.0151 (13)0.0132 (14)0.0002 (10)0.0090 (11)0.0006 (10)
C120.0159 (15)0.0087 (13)0.0159 (16)0.0001 (10)0.0071 (13)0.0001 (11)
N130.0158 (13)0.0165 (12)0.0114 (13)0.0016 (10)0.0071 (10)0.0026 (9)
C140.0200 (16)0.0101 (13)0.0153 (16)0.0019 (11)0.0107 (13)0.0003 (11)
C150.0165 (16)0.0126 (16)0.0111 (16)0.0025 (11)0.0067 (13)0.0022 (11)
Cl150.0228 (5)0.0229 (4)0.0124 (4)0.0009 (3)0.0105 (3)0.0025 (3)
C160.0201 (18)0.0088 (13)0.0134 (18)0.0030 (13)0.0056 (14)0.0007 (13)
C1210.0195 (17)0.0203 (16)0.0115 (16)0.0009 (11)0.0088 (14)0.0020 (11)
N140.0148 (13)0.0244 (15)0.0146 (13)0.0029 (10)0.0081 (11)0.0045 (10)
C1610.012 (2)0.019 (2)0.010 (2)0.0012 (11)0.0022 (19)0.0001 (10)
N210.0088 (15)0.0209 (18)0.0203 (18)0.0025 (14)0.0084 (14)0.0020 (15)
C220.0108 (17)0.0159 (18)0.0140 (19)0.0012 (12)0.0044 (15)0.0003 (13)
N230.0113 (14)0.0203 (16)0.0155 (16)0.0016 (12)0.0069 (12)0.0005 (11)
C240.0113 (17)0.0164 (17)0.0151 (19)0.0009 (13)0.0042 (15)0.0030 (13)
C250.0171 (19)0.0164 (19)0.014 (2)0.0003 (14)0.0072 (16)0.0011 (13)
Cl250.0198 (6)0.0276 (5)0.0128 (6)0.0023 (4)0.0063 (4)0.0008 (3)
C260.0151 (19)0.013 (2)0.017 (2)0.0013 (18)0.0076 (16)0.0011 (18)
C2210.0124 (19)0.031 (2)0.016 (2)0.0024 (14)0.0033 (15)0.0026 (15)
N240.0120 (15)0.0308 (19)0.0142 (16)0.0038 (12)0.0006 (12)0.0011 (12)
C2610.019 (3)0.015 (3)0.027 (3)0.0013 (16)0.014 (2)0.0012 (17)
N510.0088 (15)0.0209 (18)0.0203 (18)0.0025 (14)0.0084 (14)0.0020 (15)
C520.0108 (17)0.0159 (18)0.0140 (19)0.0012 (12)0.0044 (15)0.0003 (13)
N530.0113 (14)0.0203 (16)0.0155 (16)0.0016 (12)0.0069 (12)0.0005 (11)
C540.0113 (17)0.0164 (17)0.0151 (19)0.0009 (13)0.0042 (15)0.0030 (13)
C550.0171 (19)0.0164 (19)0.014 (2)0.0003 (14)0.0072 (16)0.0011 (13)
Cl550.0198 (6)0.0276 (5)0.0128 (6)0.0023 (4)0.0063 (4)0.0008 (3)
C560.0151 (19)0.013 (2)0.017 (2)0.0013 (18)0.0076 (16)0.0011 (18)
C5210.0124 (19)0.031 (2)0.016 (2)0.0024 (14)0.0033 (15)0.0026 (15)
N540.0120 (15)0.0308 (19)0.0142 (16)0.0038 (12)0.0006 (12)0.0011 (12)
C5610.019 (3)0.015 (3)0.027 (3)0.0013 (16)0.014 (2)0.0012 (17)
C310.0174 (18)0.0129 (14)0.0115 (17)0.0005 (13)0.0048 (14)0.0037 (12)
C320.0190 (17)0.0126 (15)0.0175 (17)0.0017 (11)0.0082 (14)0.0006 (11)
C330.0171 (17)0.0206 (15)0.0203 (18)0.0009 (12)0.0059 (14)0.0025 (12)
C340.0214 (16)0.0207 (16)0.0129 (16)0.0044 (13)0.0018 (13)0.0008 (12)
C350.0297 (18)0.0104 (14)0.0108 (16)0.0035 (12)0.0084 (14)0.0011 (10)
Cl350.0383 (5)0.0216 (4)0.0129 (4)0.0079 (3)0.0121 (4)0.0022 (3)
C360.0196 (17)0.0133 (16)0.0161 (17)0.0004 (13)0.0090 (14)0.0042 (12)
C370.0119 (18)0.0143 (18)0.012 (2)0.0032 (11)0.0004 (18)0.0046 (11)
O310.0138 (18)0.0394 (18)0.017 (2)0.0079 (9)0.0058 (16)0.0017 (9)
O320.021 (2)0.049 (2)0.0083 (18)0.0046 (10)0.0042 (17)0.0005 (9)
O330.0181 (13)0.0357 (15)0.0153 (12)0.0056 (10)0.0100 (10)0.0039 (10)
C410.012 (2)0.011 (2)0.021 (2)0.0008 (17)0.0071 (16)0.0011 (17)
C420.0149 (19)0.024 (2)0.015 (2)0.0032 (14)0.0033 (17)0.0021 (15)
C430.013 (2)0.030 (2)0.030 (2)0.0009 (16)0.0084 (17)0.0017 (17)
C440.0172 (19)0.026 (2)0.031 (2)0.0035 (15)0.0161 (18)0.0051 (16)
C450.024 (2)0.020 (2)0.017 (2)0.0046 (15)0.0111 (17)0.0017 (13)
Cl450.0359 (7)0.0301 (6)0.0181 (6)0.0059 (4)0.0153 (4)0.0023 (3)
C460.0148 (19)0.018 (2)0.017 (2)0.0002 (17)0.0052 (16)0.0012 (16)
C470.023 (3)0.015 (2)0.010 (2)0.0053 (17)0.007 (2)0.0054 (15)
O410.0129 (18)0.025 (3)0.020 (2)0.0007 (11)0.0074 (17)0.0004 (15)
O420.020 (2)0.039 (2)0.015 (2)0.0010 (18)0.0068 (18)0.002 (2)
O430.0151 (15)0.0387 (18)0.0158 (16)0.0034 (12)0.0046 (11)0.0007 (12)
C610.012 (2)0.011 (2)0.021 (2)0.0008 (17)0.0071 (16)0.0011 (17)
C620.0149 (19)0.024 (2)0.015 (2)0.0032 (14)0.0033 (17)0.0021 (15)
C630.013 (2)0.030 (2)0.030 (2)0.0009 (16)0.0084 (17)0.0017 (17)
C640.0172 (19)0.026 (2)0.031 (2)0.0035 (15)0.0161 (18)0.0051 (16)
C650.024 (2)0.020 (2)0.017 (2)0.0046 (15)0.0111 (17)0.0017 (13)
Cl650.0359 (7)0.0301 (6)0.0181 (6)0.0059 (4)0.0153 (4)0.0023 (3)
C660.0148 (19)0.018 (2)0.017 (2)0.0002 (17)0.0052 (16)0.0012 (16)
C670.0119 (18)0.0143 (18)0.012 (2)0.0032 (11)0.0004 (18)0.0046 (11)
O610.0129 (18)0.025 (3)0.020 (2)0.0007 (11)0.0074 (17)0.0004 (15)
O620.020 (2)0.039 (2)0.015 (2)0.0010 (18)0.0068 (18)0.002 (2)
O630.0151 (15)0.0387 (18)0.0158 (16)0.0034 (12)0.0046 (11)0.0007 (12)
Geometric parameters (Å, º) top
N11—C121.349 (4)C521—H52A0.9800
N11—H110.8800C521—H52B0.9800
C12—N131.310 (4)C521—H52C0.9800
C12—C1211.492 (4)N54—H54A0.8800
N13—C141.371 (4)N54—H54B0.8800
C14—C151.416 (5)C561—H56A0.9800
C15—C161.365 (5)C561—H56B0.9800
C16—N111.375 (5)C561—H56C0.9800
C14—N141.325 (4)C31—C361.395 (5)
C15—Cl151.721 (3)C31—C321.406 (5)
C16—C1611.499 (6)C31—C371.512 (6)
C121—H12A0.9800C32—O331.356 (4)
C121—H12B0.9800C32—C331.394 (5)
C121—H12C0.9800C33—C341.375 (5)
N14—H14A0.8800C33—H330.9500
N14—H14B0.8800C34—C351.390 (5)
C161—H16A0.9800C34—H340.9500
C161—H16B0.9800C35—C361.384 (5)
C161—H16C0.9800C35—Cl351.745 (3)
C37—O311.281 (6)C36—H360.9500
C37—O321.236 (7)O33—H33A0.8400
N21—C221.358 (5)C41—C461.386 (6)
N21—H210.8800C41—C421.406 (6)
C22—N231.315 (5)C41—C471.489 (7)
C22—C2211.496 (5)C42—O431.343 (5)
N23—C241.360 (5)C42—C431.393 (6)
C24—C251.420 (5)C43—C441.384 (6)
C25—C261.364 (6)C43—H430.9500
C26—N211.358 (5)C44—C451.399 (6)
C24—N241.320 (5)C44—H440.9500
C25—Cl251.731 (4)C45—C461.376 (6)
C26—C2611.480 (7)C45—Cl451.754 (4)
C221—H22A0.9800C46—H460.9500
C221—H22B0.9800C47—O411.226 (6)
C221—H22C0.9800C47—O421.301 (14)
N24—H24A0.8800O43—H43A0.8400
N24—H24B0.8800C61—C661.389 (8)
C261—H26A0.9800C61—C621.411 (7)
C261—H26B0.9800C61—C671.493 (8)
C261—H26C0.9800C62—O631.340 (7)
N51—C561.358 (7)C62—C631.392 (7)
N51—C521.358 (7)C63—C641.384 (8)
N51—H51A0.8800C63—H630.9500
C52—N531.316 (7)C64—C651.401 (8)
C52—C5211.499 (7)C64—H640.9500
N53—C541.360 (7)C65—C661.377 (7)
C54—N541.319 (7)C65—Cl651.757 (6)
C54—C551.420 (7)C66—H660.9500
C55—C561.364 (7)C67—O611.226 (8)
C55—Cl551.733 (6)C67—O621.301 (18)
C56—C5611.484 (8)O63—H63A0.8400
C12—N11—C16121.3 (3)H52A—C521—H52B109.5
C12—N11—H11119.3C52—C521—H52C109.5
C16—N11—H11119.3H52A—C521—H52C109.5
N13—C12—N11123.0 (3)H52B—C521—H52C109.5
N13—C12—C121120.0 (3)C54—N54—H54A120.0
N11—C12—C121117.0 (3)C54—N54—H54B120.0
C12—N13—C14118.5 (3)H54A—N54—H54B120.0
N14—C14—N13117.1 (3)C56—C561—H56A109.5
N14—C14—C15122.9 (3)C56—C561—H56B109.5
N13—C14—C15120.0 (3)H56A—C561—H56B109.5
C16—C15—C14119.7 (3)C56—C561—H56C109.5
C16—C15—Cl15120.8 (3)H56A—C561—H56C109.5
C14—C15—Cl15119.5 (2)H56B—C561—H56C109.5
C15—C16—N11117.4 (3)C36—C31—C32119.2 (3)
C15—C16—C161124.3 (4)C36—C31—C37121.7 (3)
N11—C16—C161118.2 (3)C32—C31—C37119.1 (3)
C12—C121—H12A109.5O33—C32—C33119.5 (3)
C12—C121—H12B109.5O33—C32—C31120.5 (3)
H12A—C121—H12B109.5C33—C32—C31120.0 (3)
C12—C121—H12C109.5C34—C33—C32119.9 (3)
H12A—C121—H12C109.5C34—C33—H33120.1
H12B—C121—H12C109.5C32—C33—H33120.1
C14—N14—H14A120.0C33—C34—C35120.7 (3)
C14—N14—H14B120.0C33—C34—H34119.7
H14A—N14—H14B120.0C35—C34—H34119.7
C16—C161—H16A109.5C36—C35—C34120.0 (3)
C16—C161—H16B109.5C36—C35—Cl35119.6 (3)
H16A—C161—H16B109.5C34—C35—Cl35120.3 (3)
C16—C161—H16C109.5C35—C36—C31120.2 (3)
H16A—C161—H16C109.5C35—C36—H36119.9
H16B—C161—H16C109.5C31—C36—H36119.9
C26—N21—C22121.6 (3)O32—C37—O31125.7 (5)
C26—N21—H21119.2O32—C37—C31118.8 (4)
C22—N21—H21119.2O31—C37—C31115.5 (4)
N23—C22—N21122.5 (4)C32—O33—H33A109.5
N23—C22—C221119.6 (3)C46—C41—C42119.9 (4)
N21—C22—C221117.8 (3)C46—C41—C47118.8 (4)
C22—N23—C24118.6 (3)C42—C41—C47121.3 (4)
N24—C24—N23117.2 (3)O43—C42—C43120.0 (4)
N24—C24—C25123.0 (4)O43—C42—C41120.9 (4)
N23—C24—C25119.8 (3)C43—C42—C41119.1 (4)
C26—C25—C24120.0 (3)C44—C43—C42120.9 (4)
C26—C25—Cl25120.7 (3)C44—C43—H43119.6
C24—C25—Cl25119.2 (3)C42—C43—H43119.6
N21—C26—C25117.3 (4)C43—C44—C45119.2 (4)
N21—C26—C261117.6 (4)C43—C44—H44120.4
C25—C26—C261125.1 (4)C45—C44—H44120.4
C22—C221—H22A109.5C46—C45—C44120.6 (4)
C22—C221—H22B109.5C46—C45—Cl45120.0 (3)
H22A—C221—H22B109.5C44—C45—Cl45119.4 (3)
C22—C221—H22C109.5C45—C46—C41120.3 (4)
H22A—C221—H22C109.5C45—C46—H46119.8
H22B—C221—H22C109.5C41—C46—H46119.8
C24—N24—H24A120.0O41—C47—O42124.5 (7)
C24—N24—H24B120.0O41—C47—C41119.5 (5)
H24A—N24—H24B120.0O42—C47—C41116.0 (6)
C26—C261—H26A109.5C42—O43—H43A109.5
C26—C261—H26B109.5C66—C61—C62118.8 (7)
H26A—C261—H26B109.5C66—C61—C67118.5 (8)
C26—C261—H26C109.5C62—C61—C67119.7 (8)
H26A—C261—H26C109.5O63—C62—C63120.5 (7)
H26B—C261—H26C109.5O63—C62—C61120.1 (7)
C56—N51—C52121.5 (7)C63—C62—C61119.0 (6)
C56—N51—H51A119.2C64—C63—C62120.7 (7)
C52—N51—H51A119.2C64—C63—H63119.6
N53—C52—N51123.1 (6)C62—C63—H63119.6
N53—C52—C521119.0 (7)C63—C64—C65119.2 (7)
N51—C52—C521117.9 (7)C63—C64—H64120.4
C52—N53—C54118.0 (6)C65—C64—H64120.4
N54—C54—N53116.5 (7)C66—C65—C64120.0 (6)
N54—C54—C55123.8 (7)C66—C65—Cl65120.9 (6)
N53—C54—C55119.8 (6)C64—C65—Cl65119.1 (6)
C56—C55—C54120.5 (6)C65—C66—C61120.4 (7)
C56—C55—Cl55120.2 (6)C65—C66—H66119.8
C54—C55—Cl55119.3 (6)C61—C66—H66119.8
N51—C56—C55116.9 (6)O61—C67—O62124.5 (13)
N51—C56—C561117.0 (8)O61—C67—C61119.6 (9)
C55—C56—C561124.7 (8)O62—C67—C61115.7 (8)
C52—C521—H52A109.5C62—O63—H63A109.5
C52—C521—H52B109.5
C16—N11—C12—N130.1 (5)C36—C31—C32—C330.2 (5)
C16—N11—C12—C121179.4 (3)C37—C31—C32—C33179.6 (3)
N11—C12—N13—C141.6 (5)O33—C32—C33—C34179.1 (3)
C121—C12—N13—C14177.8 (3)C31—C32—C33—C340.8 (5)
C12—N13—C14—N14178.7 (3)C32—C33—C34—C350.8 (5)
C12—N13—C14—C151.4 (5)C33—C34—C35—C360.2 (5)
N14—C14—C15—C16179.6 (3)C33—C34—C35—Cl35179.8 (3)
N13—C14—C15—C160.3 (5)C34—C35—C36—C310.3 (5)
N14—C14—C15—Cl151.8 (5)Cl35—C35—C36—C31179.6 (3)
N13—C14—C15—Cl15178.1 (3)C32—C31—C36—C350.3 (5)
C14—C15—C16—N111.7 (5)C37—C31—C36—C35179.1 (3)
Cl15—C15—C16—N11179.6 (3)C36—C31—C37—O32178.9 (3)
C14—C15—C16—C161178.1 (3)C32—C31—C37—O320.5 (5)
Cl15—C15—C16—C1610.2 (5)C36—C31—C37—O311.8 (5)
C12—N11—C16—C151.6 (5)C32—C31—C37—O31178.8 (3)
C12—N11—C16—C161178.2 (3)C46—C41—C42—O43179.9 (4)
C26—N21—C22—N231.5 (6)C47—C41—C42—O430.0 (6)
C26—N21—C22—C221178.7 (4)C46—C41—C42—C430.2 (6)
N21—C22—N23—C242.6 (6)C47—C41—C42—C43179.6 (4)
C221—C22—N23—C24177.7 (3)O43—C42—C43—C44178.3 (4)
C22—N23—C24—N24178.4 (3)C41—C42—C43—C442.0 (6)
C22—N23—C24—C251.7 (5)C42—C43—C44—C452.7 (6)
N24—C24—C25—C26179.7 (4)C43—C44—C45—C461.6 (6)
N23—C24—C25—C260.1 (6)C43—C44—C45—Cl45179.1 (3)
N24—C24—C25—Cl251.6 (5)C44—C45—C46—C410.2 (6)
N23—C24—C25—Cl25178.3 (3)Cl45—C45—C46—C41179.1 (3)
C22—N21—C26—C250.4 (6)C42—C41—C46—C450.9 (6)
C22—N21—C26—C261176.3 (4)C47—C41—C46—C45179.3 (4)
C24—C25—C26—N211.2 (6)C46—C41—C47—O412.7 (7)
Cl25—C25—C26—N21179.3 (3)C42—C41—C47—O41177.1 (4)
C24—C25—C26—C261175.3 (4)C46—C41—C47—O42176 (3)
Cl25—C25—C26—C2612.9 (6)C42—C41—C47—O424 (3)
C56—N51—C52—N535 (3)C66—C61—C62—O63174.8 (18)
C56—N51—C52—C521176.9 (19)C67—C61—C62—O6315 (3)
N51—C52—N53—C545 (3)C66—C61—C62—C6313 (3)
C521—C52—N53—C54177.1 (18)C67—C61—C62—C63173 (2)
C52—N53—C54—N54178.1 (17)O63—C62—C63—C64173.8 (19)
C52—N53—C54—C553 (3)C61—C62—C63—C642 (3)
N54—C54—C55—C56179.5 (19)C62—C63—C64—C658 (3)
N53—C54—C55—C562 (3)C63—C64—C65—C666 (3)
N54—C54—C55—Cl552 (3)C63—C64—C65—Cl65174.1 (16)
N53—C54—C55—Cl55176.4 (15)C64—C65—C66—C616 (3)
C52—N51—C56—C553 (3)Cl65—C65—C66—C61174.4 (15)
C52—N51—C56—C561170 (2)C62—C61—C66—C6515 (3)
C54—C55—C56—N512 (3)C67—C61—C66—C65175 (2)
Cl55—C55—C56—N51176.4 (16)C66—C61—C67—O611 (4)
C54—C55—C56—C561167 (2)C62—C61—C67—O61161 (3)
Cl55—C55—C56—C56111 (3)C66—C61—C67—O62176 (13)
C36—C31—C32—O33179.7 (3)C62—C61—C67—O6224 (14)
C37—C31—C32—O330.3 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O410.881.732.597 (6)166
N14—H14A···N13i0.882.353.180 (4)156
N14—H14B···O330.882.102.874 (4)147
O33—H33A···O320.841.732.483 (5)148
N21—H21···O310.881.742.605 (5)166
N24—H24A···N23ii0.882.343.163 (5)156
N24—H24B···O43iii0.882.112.897 (4)148
O43—H43A···O420.841.732.487 (13)149
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y, z+1; (iii) x1, y+1/2, z1/2.
2-Amino-4,6-dimethoxypyrimidin-1ium thiophene-2-carboxylate (III) top
Crystal data top
C6H10N3O2+·C5H3O2SF(000) = 592
Mr = 283.30Dx = 1.465 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 6.7335 (3) ÅCell parameters from 4262 reflections
b = 7.6307 (4) Åθ = 3.1–32.7°
c = 25.0638 (10) ŵ = 0.27 mm1
β = 93.928 (4)°T = 173 K
V = 1284.79 (10) Å3Block, colourless
Z = 40.32 × 0.28 × 0.14 mm
Data collection top
Agilent Eos Gemini
diffractometer
4262 independent reflections
Radiation source: fine-focus sealed tube3087 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 16.0416 pixels mm-1θmax = 32.7°, θmin = 3.1°
ω scansh = 79
Absorption correction: multi-scan
(CrysAlis RED; Agilent, 2012)
k = 1110
Tmin = 0.752, Tmax = 0.963l = 3633
8880 measured reflections
Refinement top
Refinement on F218 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.119 w = 1/[σ2(Fo2) + (0.0496P)2 + 0.2546P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
4262 reflectionsΔρmax = 0.32 e Å3
199 parametersΔρmin = 0.32 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.32086 (15)0.14245 (14)0.38771 (4)0.0299 (2)
O20.23128 (15)0.13436 (16)0.57313 (4)0.0344 (3)
N10.53923 (16)0.26187 (16)0.44754 (5)0.0246 (2)
H10.60720.29250.42030.030*
N20.50876 (17)0.26067 (16)0.54142 (5)0.0255 (2)
N30.78320 (18)0.37857 (19)0.50524 (5)0.0347 (3)
H310.83230.40420.53770.042*
H320.85040.40520.47750.042*
C10.6089 (2)0.30031 (19)0.49822 (5)0.0244 (3)
C20.3648 (2)0.17616 (18)0.43932 (5)0.0238 (3)
C30.2552 (2)0.13067 (19)0.48119 (6)0.0271 (3)
H30.13190.07050.47620.033*
C40.3372 (2)0.17884 (19)0.53174 (6)0.0256 (3)
C50.1469 (2)0.0368 (2)0.37448 (6)0.0355 (4)
H5A0.13140.01940.33570.053*
H5B0.02890.09630.38650.053*
H5C0.16210.07720.39230.053*
C60.3181 (2)0.1691 (3)0.62629 (6)0.0370 (4)
H6A0.36380.29100.62850.056*
H6B0.43130.09030.63410.056*
H6C0.21820.14960.65230.056*
S1A0.84749 (8)0.54595 (10)0.26446 (2)0.0376 (2)0.8687 (19)
C1A1.0432 (3)0.6531 (4)0.23815 (9)0.0400 (5)0.8687 (19)
H1A1.03780.70230.20330.048*0.8687 (19)
C2A1.2064 (5)0.6590 (7)0.27308 (10)0.0419 (6)0.8687 (19)
H2A1.32890.71260.26580.050*0.8687 (19)
C3A1.1710 (7)0.5762 (11)0.3210 (2)0.0372 (8)0.8687 (19)
H3A1.26950.56770.34980.045*0.8687 (19)
C4A0.9862 (5)0.5089 (8)0.32334 (11)0.0262 (4)0.8687 (19)
C5A0.8972 (6)0.4271 (10)0.36979 (11)0.0260 (5)0.8687 (19)
O1A0.9959 (4)0.4296 (3)0.41382 (9)0.0309 (5)0.8687 (19)
O2A0.7246 (5)0.3595 (8)0.36208 (12)0.0364 (6)0.8687 (19)
S1B1.2152 (14)0.568 (2)0.3275 (5)0.0372 (8)0.1313 (19)
C1B1.184 (3)0.648 (5)0.2632 (7)0.0419 (6)0.1313 (19)
H1B1.28870.69680.24430.050*0.1313 (19)
C2B0.993 (2)0.633 (3)0.2428 (6)0.0400 (5)0.1313 (19)
H2B0.94290.68300.20980.048*0.1313 (19)
C3B0.880 (2)0.536 (3)0.2766 (6)0.03757 (17)0.1313 (19)
H3B0.74660.50300.26700.045*0.1313 (19)
C4B0.975 (3)0.492 (5)0.3241 (7)0.0262 (4)0.1313 (19)
C5B0.884 (4)0.431 (7)0.3731 (7)0.0260 (5)0.1313 (19)
O1B0.975 (3)0.466 (3)0.4169 (7)0.0309 (5)0.1313 (19)
O2B0.707 (4)0.370 (6)0.3680 (9)0.0364 (6)0.1313 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0302 (5)0.0367 (6)0.0230 (5)0.0081 (4)0.0039 (4)0.0050 (4)
O20.0341 (6)0.0459 (7)0.0245 (5)0.0043 (5)0.0112 (4)0.0020 (5)
N10.0265 (5)0.0272 (6)0.0205 (5)0.0031 (5)0.0049 (4)0.0005 (4)
N20.0284 (6)0.0280 (6)0.0204 (5)0.0013 (5)0.0052 (4)0.0011 (5)
N30.0338 (7)0.0498 (9)0.0206 (6)0.0144 (6)0.0024 (5)0.0009 (5)
C10.0283 (7)0.0241 (7)0.0211 (6)0.0006 (5)0.0037 (5)0.0010 (5)
C20.0260 (6)0.0227 (7)0.0231 (6)0.0002 (5)0.0034 (5)0.0013 (5)
C30.0256 (6)0.0289 (7)0.0273 (7)0.0029 (5)0.0054 (5)0.0012 (6)
C40.0287 (7)0.0248 (7)0.0241 (6)0.0039 (5)0.0082 (5)0.0029 (5)
C50.0341 (8)0.0396 (9)0.0327 (8)0.0093 (7)0.0007 (6)0.0072 (7)
C60.0393 (8)0.0509 (10)0.0219 (7)0.0044 (7)0.0098 (6)0.0003 (7)
S1A0.0422 (3)0.0527 (3)0.0175 (3)0.0001 (2)0.00008 (17)0.0023 (2)
C1A0.0570 (15)0.0417 (13)0.0233 (8)0.0003 (11)0.0172 (9)0.0070 (7)
C2A0.0504 (12)0.0451 (13)0.0315 (13)0.0122 (10)0.0128 (9)0.0005 (15)
C3A0.042 (2)0.0423 (11)0.0267 (17)0.004 (2)0.0017 (14)0.0037 (11)
C4A0.0327 (8)0.0277 (15)0.0185 (6)0.0002 (6)0.0036 (5)0.0004 (6)
C5A0.0301 (9)0.0283 (9)0.0199 (7)0.0014 (9)0.0042 (6)0.0009 (8)
O1A0.0323 (9)0.0400 (14)0.0203 (6)0.0041 (8)0.0009 (5)0.0023 (7)
O2A0.0352 (9)0.0538 (13)0.0205 (10)0.0147 (10)0.0034 (6)0.0001 (10)
S1B0.042 (2)0.0423 (11)0.0267 (17)0.004 (2)0.0017 (14)0.0037 (11)
C1B0.0504 (12)0.0451 (13)0.0315 (13)0.0122 (10)0.0128 (9)0.0005 (15)
C2B0.0570 (15)0.0417 (13)0.0233 (8)0.0003 (11)0.0172 (9)0.0070 (7)
C3B0.0422 (3)0.0527 (3)0.0175 (3)0.0001 (2)0.00008 (17)0.0023 (2)
C4B0.0327 (8)0.0277 (15)0.0185 (6)0.0002 (6)0.0036 (5)0.0004 (6)
C5B0.0301 (9)0.0283 (9)0.0199 (7)0.0014 (9)0.0042 (6)0.0009 (8)
O1B0.0323 (9)0.0400 (14)0.0203 (6)0.0041 (8)0.0009 (5)0.0023 (7)
O2B0.0352 (9)0.0538 (13)0.0205 (10)0.0147 (10)0.0034 (6)0.0001 (10)
Geometric parameters (Å, º) top
O1—C21.3320 (16)S1A—C1A1.720 (2)
O1—C51.4421 (18)C1A—C2A1.358 (3)
O2—C41.3423 (15)C1A—H1A0.9500
O2—C61.4424 (19)C2A—C3A1.391 (6)
N1—C21.3479 (17)C2A—H2A0.9500
N1—C11.3558 (17)C3A—C4A1.352 (5)
N1—H10.8803C3A—H3A0.9500
N2—C41.3208 (19)C4A—C5A1.483 (2)
N2—C11.3484 (16)C5A—O1A1.249 (2)
N3—C11.3179 (18)C5A—O2A1.2742 (19)
N3—H310.8790S1B—C4B1.716 (6)
N3—H320.8788S1B—C1B1.721 (5)
C2—C31.3681 (18)C1B—C2B1.358 (5)
C3—C41.396 (2)C1B—H1B0.9500
C3—H30.9500C2B—C3B1.389 (7)
C5—H5A0.9800C2B—H2B0.9500
C5—H5B0.9800C3B—C4B1.353 (7)
C5—H5C0.9800C3B—H3B0.9500
C6—H6A0.9800C4B—C5B1.485 (5)
C6—H6B0.9800C5B—O1B1.249 (5)
C6—H6C0.9800C5B—O2B1.274 (5)
S1A—C4A1.715 (2)
C2—O1—C5117.00 (11)C4A—S1A—C1A91.26 (11)
C4—O2—C6117.66 (12)C2A—C1A—S1A112.08 (17)
C2—N1—C1119.36 (11)C2A—C1A—H1A124.0
C2—N1—H1120.3S1A—C1A—H1A124.0
C1—N1—H1120.4C1A—C2A—C3A111.2 (2)
C4—N2—C1115.96 (12)C1A—C2A—H2A124.4
C1—N3—H31120.0C3A—C2A—H2A124.4
C1—N3—H32120.1C4A—C3A—C2A115.1 (3)
H31—N3—H32120.0C4A—C3A—H3A122.5
N3—C1—N2118.96 (13)C2A—C3A—H3A122.5
N3—C1—N1118.10 (12)C3A—C4A—C5A128.1 (3)
N2—C1—N1122.94 (13)C3A—C4A—S1A110.4 (2)
O1—C2—N1112.05 (11)C5A—C4A—S1A121.30 (17)
O1—C2—C3126.90 (13)O1A—C5A—O2A124.4 (2)
N1—C2—C3121.05 (13)O1A—C5A—C4A117.93 (16)
C2—C3—C4115.39 (13)O2A—C5A—C4A117.69 (18)
C2—C3—H3122.3C4B—S1B—C1B91.1 (4)
C4—C3—H3122.3C2B—C1B—S1B112.0 (5)
N2—C4—O2118.81 (13)C2B—C1B—H1B124.0
N2—C4—C3125.28 (12)S1B—C1B—H1B124.0
O2—C4—C3115.90 (13)C1B—C2B—C3B111.0 (6)
O1—C5—H5A109.5C1B—C2B—H2B124.5
O1—C5—H5B109.5C3B—C2B—H2B124.5
H5A—C5—H5B109.5C4B—C3B—C2B115.1 (6)
O1—C5—H5C109.5C4B—C3B—H3B122.4
H5A—C5—H5C109.5C2B—C3B—H3B122.4
H5B—C5—H5C109.5C3B—C4B—C5B127.6 (10)
O2—C6—H6A109.5C3B—C4B—S1B110.2 (5)
O2—C6—H6B109.5C5B—C4B—S1B120.4 (7)
H6A—C6—H6B109.5O1B—C5B—O2B124.3 (10)
O2—C6—H6C109.5O1B—C5B—C4B117.1 (7)
H6A—C6—H6C109.5O2B—C5B—C4B117.8 (7)
H6B—C6—H6C109.5
C4—N2—C1—N3178.52 (14)C2A—C3A—C4A—C5A174.4 (6)
C4—N2—C1—N10.9 (2)C2A—C3A—C4A—S1A0.4 (9)
C2—N1—C1—N3177.61 (13)C1A—S1A—C4A—C3A0.3 (5)
C2—N1—C1—N21.8 (2)C1A—S1A—C4A—C5A174.9 (4)
C5—O1—C2—N1174.35 (13)C3A—C4A—C5A—O1A5.7 (9)
C5—O1—C2—C34.5 (2)S1A—C4A—C5A—O1A168.6 (6)
C1—N1—C2—O1177.61 (12)C3A—C4A—C5A—O2A174.6 (9)
C1—N1—C2—C31.4 (2)S1A—C4A—C5A—O2A11.1 (8)
O1—C2—C3—C4178.68 (14)C4B—S1B—C1B—C2B6 (3)
N1—C2—C3—C40.1 (2)S1B—C1B—C2B—C3B8 (4)
C1—N2—C4—O2179.40 (13)C1B—C2B—C3B—C4B6 (4)
C1—N2—C4—C30.5 (2)C2B—C3B—C4B—C5B163 (3)
C6—O2—C4—N23.9 (2)C2B—C3B—C4B—S1B2 (4)
C6—O2—C4—C3175.14 (13)C1B—S1B—C4B—C3B3 (3)
C2—C3—C4—N20.8 (2)C1B—S1B—C4B—C5B168 (3)
C2—C3—C4—O2179.79 (13)C3B—C4B—C5B—O1B151 (5)
C4A—S1A—C1A—C2A0.2 (4)S1B—C4B—C5B—O1B12 (5)
S1A—C1A—C2A—C3A0.0 (6)C3B—C4B—C5B—O2B19 (6)
C1A—C2A—C3A—C4A0.3 (9)S1B—C4B—C5B—O2B178 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2A0.881.782.658 (4)175
N3—H31···O1Ai0.882.062.839 (3)148
N3—H32···O1A0.881.942.811 (3)172
N1—H1···O2B0.881.622.50 (3)172
N3—H31···O1Bi0.881.942.73 (2)148
N3—H32···O1B0.881.842.722 (19)176
Symmetry code: (i) x+2, y+1, z+1.
 

Subscribe to Acta Crystallographica Section C: Structural Chemistry

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds