Buy article online - an online subscription or single-article purchase is required to access this article.
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, C
6H
9ClN
3+·C
7H
4ClO
3−, 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
P2
1/
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, C
6H
10N
3O
2+·C
5H
3O
2S
−, (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
CCDC references: 1405154; 1575633; 1575632
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+·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) Å3 | 0.24 × 0.07 × 0.05 mm |
Data collection top
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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.032 | H 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 reflections | Δρmax = 0.34 e Å−3 |
407 parameters | Δρmin = −0.26 e Å−3 |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···O33i | 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···O43ii | 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)
top
Crystal data top
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) Å3 | Block, colourless |
Z = 8 | 0.10 × 0.04 × 0.04 mm |
Data collection top
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 top
Refinement on F2 | 50 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-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 reflections | Δρmax = 0.51 e Å−3 |
454 parameters | Δρmin = −0.40 e Å−3 |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···N13i | 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···N23ii | 0.88 | 2.34 | 3.163 (5) | 156 |
N24—H24B···O43iii | 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)
top
Crystal data top
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) Å3 | Block, colourless |
Z = 4 | 0.32 × 0.28 × 0.14 mm |
Data collection top
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 top
Refinement on F2 | 18 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.047 | H-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 reflections | Δρmax = 0.32 e Å−3 |
199 parameters | Δρmin = −0.32 e Å−3 |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···O1Ai | 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···O1Bi | 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. |
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.