The organic components of 2-methoxy-3-methyl-6-oxo-4-(2,3,4-tri-
O-acetyl-β-
D-xylopyranosylamino)-1,6-dihydropyrimidine-5-carbaldehyde 0.065-hydrate, C
18H
23N
3O
10·0.065H
2O, (I), which crystallizes with
Z′ = 2 in the space group
P2
12
12
1, are linked into a three-dimensional framework structure by a combination of four C—H
O hydrogen bonds. In 2-methylsulfanyl-6-oxo-4-(2,3,4-tri-
O-acetyl-β-
D-xylopyranosylamino)-1,6-dihydropyrimidine-5-carbaldehyde, C
17H
21N
3O
9S, (II), where the pyrimidine fragment is disordered with two different conformations for the methylsulfanyl substituent, molecules are linked into chains of rings by a combination of N—H
O and C—H
O hydrogen bonds.
Supporting information
CCDC references: 742242; 742243
Samples of (I) and (II) were prepared according to the published procedure of
Negrillo et al. (1988) and were recrystallized from ethanol.
With the exception of the H atoms of the water component in (I) and the H atoms
in the minor component of the pyrimidine unit in (II), all H atoms were
located in difference maps. Those which could not be located directly were
included in calculated positions, and then all H atoms bonded to C or N atoms
were treated as riding atoms in geometrically idealized positions, with C—H
= 0.95 (formyl), 0.98 (CH3), 0.99 (CH2) or 1.00Å (aliphatic C—H) and
N—H = 0.88Å, and with Uiso(H) = kUeq(carrier), where
k = 1.5 for the methyl groups, which were permitted to rotate but not
to tilt, and k = 1.2 for all other H atoms. For the partial water
component of (I), the O—H and H···H distances were subject to the restraints
0.84 (1) and 1.34 (1)Å, respectively, and the refined occupancy was 0.065 (3)
molecules of water per molecule of the organic component. For (II), all atoms
apart from those of the sugar moiety were included in the disorder model, with
the bond distances and one-angle nonbonded distances in the minor B
component constrained to have the same values as the corresponding distances
in the major A component, subject to an s.u. of 0.005Å, while the distances
N16n—C16n (n = A or B) were both subject
to the distance constraint 1.40 (2)Å. In addition, it was necessary to
constrain corresponding atoms in the two components to have the same
anisotropic displacement parameter components, apart from atoms S1n and
C17n, which were subject to rigid-bond restraints, via DELU and
ISOR, with s.u. values 0.015 and 0.010Å2, respectively. Subject to these
conditions, the refined occupancies for the two disorder components were
0.899 (2) and 0.101 (2), respectively. For (II), the correct absolute
configuration was established by means of the Flack x parameter (Flack,
1983) of -0.02 (7) and the Hooft y parameter (Hooft et
al., 2008)
of -0.003 (31), calculated in each case for 1900 Bijvoet pairs from a possible
maximum of 1911, i.e. 99.4% coverage. In the absence of significant
resonant scattering in (I), it was not possible to determine the absolute
configuration directly; accordingly, the Friedel-equivalent reflections were
merged prior to the final refinements, and the absolute configuration was set
by reference to that in (II).
For both compounds, data collection: COLLECT (Hooft, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
(I) 2-Methoxy-3-methyl-6-oxo-4-(2,3,4-tri-
O-acetyl-
β-D-xylopyranosylamino)-
1,6-dihydropyrimidine-5-carbaldehyde 0.065-hydrate
top
Crystal data top
C18H23N3O10·0.065H2O | F(000) = 1861 |
Mr = 442.57 | Dx = 1.378 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 5407 reflections |
a = 14.3816 (2) Å | θ = 3.2–27.5° |
b = 14.7626 (2) Å | µ = 0.11 mm−1 |
c = 20.1025 (3) Å | T = 120 K |
V = 4267.96 (10) Å3 | Block, colourless |
Z = 8 | 0.22 × 0.20 × 0.18 mm |
Data collection top
Bruker–Nonius KappaCCD diffractometer | 5407 independent reflections |
Radiation source: Bruker–Nonius FR591 rotating anode | 4925 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.2° |
ϕ and ω scans | h = −18→18 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | k = −19→19 |
Tmin = 0.975, Tmax = 0.980 | l = −26→26 |
70888 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.088 | w = 1/[σ2(Fo2) + (0.0543P)2 + 0.5385P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
5407 reflections | Δρmax = 0.24 e Å−3 |
581 parameters | Δρmin = −0.20 e Å−3 |
3 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0044 (6) |
Crystal data top
C18H23N3O10·0.065H2O | V = 4267.96 (10) Å3 |
Mr = 442.57 | Z = 8 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 14.3816 (2) Å | µ = 0.11 mm−1 |
b = 14.7626 (2) Å | T = 120 K |
c = 20.1025 (3) Å | 0.22 × 0.20 × 0.18 mm |
Data collection top
Bruker–Nonius KappaCCD diffractometer | 5407 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 4925 reflections with I > 2σ(I) |
Tmin = 0.975, Tmax = 0.980 | Rint = 0.041 |
70888 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.033 | 3 restraints |
wR(F2) = 0.088 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.24 e Å−3 |
5407 reflections | Δρmin = −0.20 e Å−3 |
581 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
N11 | 0.55855 (11) | 0.24150 (11) | 0.62212 (8) | 0.0215 (3) | |
C12 | 0.54814 (13) | 0.15386 (13) | 0.61908 (9) | 0.0218 (4) | |
N13 | 0.48420 (11) | 0.10372 (10) | 0.65175 (8) | 0.0230 (3) | |
C14 | 0.42119 (13) | 0.14549 (13) | 0.69612 (9) | 0.0219 (4) | |
C15 | 0.43334 (13) | 0.24172 (13) | 0.70370 (9) | 0.0203 (4) | |
C16 | 0.50035 (13) | 0.28629 (12) | 0.66423 (9) | 0.0198 (4) | |
O12 | 0.60332 (10) | 0.10425 (10) | 0.58065 (7) | 0.0289 (3) | |
C121 | 0.67981 (15) | 0.15069 (16) | 0.54824 (12) | 0.0338 (5) | |
H12A | 0.7201 | 0.1782 | 0.5820 | 0.051* | |
H12B | 0.6552 | 0.1981 | 0.5190 | 0.051* | |
H12C | 0.7158 | 0.1072 | 0.5219 | 0.051* | |
C13 | 0.47977 (16) | 0.00484 (13) | 0.64318 (11) | 0.0303 (5) | |
H13A | 0.4629 | −0.0093 | 0.5971 | 0.045* | |
H13B | 0.4329 | −0.0203 | 0.6734 | 0.045* | |
H13C | 0.5406 | −0.0217 | 0.6534 | 0.045* | |
O14 | 0.36304 (11) | 0.09911 (10) | 0.72463 (7) | 0.0308 (3) | |
C51 | 0.37858 (14) | 0.28639 (13) | 0.75333 (10) | 0.0228 (4) | |
H51 | 0.3348 | 0.2509 | 0.7772 | 0.027* | |
O51 | 0.38407 (10) | 0.36808 (9) | 0.76745 (7) | 0.0268 (3) | |
N16 | 0.51011 (11) | 0.37678 (10) | 0.66764 (8) | 0.0215 (3) | |
H16 | 0.4735 | 0.4073 | 0.6947 | 0.026* | |
C21 | 0.57743 (13) | 0.42591 (12) | 0.62928 (10) | 0.0210 (4) | |
H21 | 0.5809 | 0.4009 | 0.5831 | 0.025* | |
C22 | 0.54980 (13) | 0.52631 (13) | 0.62743 (10) | 0.0212 (4) | |
H22 | 0.5391 | 0.5491 | 0.6736 | 0.025* | |
C23 | 0.62576 (13) | 0.58076 (12) | 0.59419 (10) | 0.0208 (4) | |
H23 | 0.6295 | 0.5649 | 0.5459 | 0.025* | |
C24 | 0.71839 (13) | 0.56305 (13) | 0.62761 (10) | 0.0225 (4) | |
H24 | 0.7174 | 0.5855 | 0.6745 | 0.027* | |
C25 | 0.73790 (14) | 0.46158 (13) | 0.62595 (11) | 0.0252 (4) | |
H25A | 0.7396 | 0.4398 | 0.5794 | 0.030* | |
H25B | 0.7988 | 0.4486 | 0.6468 | 0.030* | |
O26 | 0.66507 (9) | 0.41678 (9) | 0.66179 (7) | 0.0246 (3) | |
O22 | 0.46700 (9) | 0.53734 (9) | 0.58827 (7) | 0.0243 (3) | |
C221 | 0.38547 (14) | 0.54845 (13) | 0.62114 (11) | 0.0277 (4) | |
O221 | 0.37893 (11) | 0.54460 (11) | 0.68085 (8) | 0.0378 (4) | |
C222 | 0.30731 (15) | 0.56670 (17) | 0.57410 (13) | 0.0382 (5) | |
H22A | 0.3063 | 0.6313 | 0.5628 | 0.057* | |
H22B | 0.2483 | 0.5498 | 0.5951 | 0.057* | |
H22C | 0.3161 | 0.5310 | 0.5335 | 0.057* | |
O23 | 0.60521 (10) | 0.67618 (9) | 0.60197 (6) | 0.0238 (3) | |
C231 | 0.58914 (15) | 0.72517 (14) | 0.54637 (10) | 0.0282 (4) | |
O231 | 0.58183 (14) | 0.69321 (12) | 0.49217 (8) | 0.0451 (5) | |
C232 | 0.5801 (2) | 0.82334 (15) | 0.56262 (13) | 0.0454 (6) | |
H23A | 0.5145 | 0.8381 | 0.5701 | 0.068* | |
H23B | 0.6040 | 0.8596 | 0.5255 | 0.068* | |
H23C | 0.6159 | 0.8369 | 0.6029 | 0.068* | |
O24 | 0.78850 (9) | 0.61050 (9) | 0.58946 (7) | 0.0251 (3) | |
C241 | 0.83126 (14) | 0.68144 (15) | 0.61893 (11) | 0.0294 (4) | |
O241 | 0.82119 (13) | 0.70105 (14) | 0.67621 (9) | 0.0523 (5) | |
C242 | 0.89103 (17) | 0.73180 (15) | 0.57108 (12) | 0.0371 (5) | |
H24A | 0.9561 | 0.7276 | 0.5852 | 0.056* | |
H24B | 0.8721 | 0.7955 | 0.5700 | 0.056* | |
H24C | 0.8842 | 0.7054 | 0.5266 | 0.056* | |
N31 | 0.56643 (11) | 0.23884 (11) | 0.39917 (8) | 0.0224 (3) | |
C32 | 0.56474 (13) | 0.15069 (13) | 0.39628 (10) | 0.0229 (4) | |
N33 | 0.50463 (11) | 0.09540 (11) | 0.42829 (8) | 0.0235 (4) | |
C34 | 0.43784 (14) | 0.13218 (14) | 0.47255 (10) | 0.0235 (4) | |
C35 | 0.43767 (14) | 0.22933 (13) | 0.47719 (10) | 0.0231 (4) | |
C36 | 0.50126 (13) | 0.27904 (13) | 0.43867 (9) | 0.0206 (4) | |
O32 | 0.62713 (10) | 0.10542 (10) | 0.36094 (8) | 0.0296 (3) | |
C321 | 0.69918 (16) | 0.15819 (16) | 0.32828 (12) | 0.0359 (5) | |
H32A | 0.7295 | 0.1977 | 0.3609 | 0.054* | |
H32B | 0.6713 | 0.1953 | 0.2931 | 0.054* | |
H32C | 0.7454 | 0.1172 | 0.3088 | 0.054* | |
C33 | 0.50724 (16) | −0.00296 (14) | 0.41756 (13) | 0.0350 (5) | |
H33A | 0.4542 | −0.0312 | 0.4401 | 0.052* | |
H33B | 0.5653 | −0.0275 | 0.4357 | 0.052* | |
H33C | 0.5040 | −0.0158 | 0.3698 | 0.052* | |
O34 | 0.38674 (10) | 0.08067 (10) | 0.50337 (8) | 0.0313 (3) | |
C53 | 0.37410 (14) | 0.27053 (14) | 0.52295 (10) | 0.0264 (4) | |
H53 | 0.3347 | 0.2311 | 0.5475 | 0.032* | |
O53 | 0.36572 (10) | 0.35231 (10) | 0.53346 (7) | 0.0308 (3) | |
N36 | 0.50076 (11) | 0.37048 (11) | 0.43931 (8) | 0.0238 (3) | |
H36 | 0.4595 | 0.3986 | 0.4642 | 0.029* | |
C41 | 0.56495 (13) | 0.42343 (13) | 0.40099 (10) | 0.0223 (4) | |
H41 | 0.5855 | 0.3878 | 0.3613 | 0.027* | |
C42 | 0.52077 (13) | 0.51266 (13) | 0.37773 (10) | 0.0219 (4) | |
H42 | 0.4979 | 0.5490 | 0.4164 | 0.026* | |
C43 | 0.59237 (13) | 0.56491 (12) | 0.33805 (9) | 0.0206 (4) | |
H43 | 0.6059 | 0.5324 | 0.2955 | 0.025* | |
C44 | 0.68144 (13) | 0.57653 (12) | 0.37760 (10) | 0.0214 (4) | |
H44 | 0.6707 | 0.6184 | 0.4159 | 0.026* | |
C45 | 0.71626 (13) | 0.48519 (14) | 0.40262 (11) | 0.0262 (4) | |
H45A | 0.7325 | 0.4458 | 0.3645 | 0.031* | |
H45B | 0.7726 | 0.4937 | 0.4302 | 0.031* | |
O46 | 0.64374 (9) | 0.44355 (9) | 0.44162 (7) | 0.0251 (3) | |
O42 | 0.44569 (9) | 0.49149 (10) | 0.33244 (7) | 0.0259 (3) | |
C421 | 0.35756 (14) | 0.49991 (14) | 0.35479 (11) | 0.0287 (4) | |
O421 | 0.33856 (11) | 0.52294 (13) | 0.41028 (9) | 0.0425 (4) | |
C422 | 0.28865 (16) | 0.47422 (18) | 0.30211 (12) | 0.0388 (5) | |
H42A | 0.2360 | 0.5164 | 0.3033 | 0.058* | |
H42B | 0.2663 | 0.4125 | 0.3103 | 0.058* | |
H42C | 0.3186 | 0.4770 | 0.2584 | 0.058* | |
O43 | 0.55693 (10) | 0.65436 (9) | 0.32390 (7) | 0.0236 (3) | |
C431 | 0.55734 (14) | 0.68219 (14) | 0.26010 (10) | 0.0259 (4) | |
O432 | 0.57219 (12) | 0.63377 (11) | 0.21329 (7) | 0.0385 (4) | |
C432 | 0.53632 (19) | 0.78155 (15) | 0.25651 (12) | 0.0383 (5) | |
H43A | 0.4703 | 0.7916 | 0.2662 | 0.057* | |
H43B | 0.5505 | 0.8040 | 0.2118 | 0.057* | |
H43C | 0.5744 | 0.8140 | 0.2892 | 0.057* | |
O44 | 0.74702 (9) | 0.61608 (9) | 0.33157 (7) | 0.0249 (3) | |
C441 | 0.80981 (14) | 0.67443 (14) | 0.35627 (11) | 0.0296 (4) | |
O441 | 0.82016 (14) | 0.68736 (15) | 0.41453 (9) | 0.0567 (6) | |
C442 | 0.86416 (17) | 0.71843 (16) | 0.30227 (12) | 0.0375 (5) | |
H44A | 0.9280 | 0.7289 | 0.3175 | 0.056* | |
H44B | 0.8353 | 0.7765 | 0.2906 | 0.056* | |
H44C | 0.8650 | 0.6790 | 0.2631 | 0.056* | |
O61 | 0.7788 (10) | 0.2493 (10) | 0.6595 (7) | 0.043 (4)* | 0.130 (6) |
H61 | 0.740 (9) | 0.253 (15) | 0.690 (6) | 0.051* | 0.130 (6) |
H62 | 0.829 (6) | 0.270 (14) | 0.675 (8) | 0.051* | 0.130 (6) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N11 | 0.0203 (7) | 0.0230 (8) | 0.0211 (8) | −0.0004 (6) | −0.0013 (7) | −0.0005 (6) |
C12 | 0.0206 (9) | 0.0234 (9) | 0.0212 (9) | 0.0021 (7) | −0.0038 (7) | −0.0010 (7) |
N13 | 0.0281 (8) | 0.0175 (7) | 0.0232 (8) | 0.0003 (6) | −0.0010 (7) | 0.0008 (6) |
C14 | 0.0230 (9) | 0.0231 (9) | 0.0197 (9) | −0.0023 (8) | −0.0040 (7) | 0.0015 (7) |
C15 | 0.0205 (9) | 0.0215 (9) | 0.0189 (9) | −0.0023 (7) | −0.0032 (7) | 0.0004 (7) |
C16 | 0.0192 (8) | 0.0217 (9) | 0.0186 (9) | 0.0002 (7) | −0.0039 (7) | −0.0001 (7) |
O12 | 0.0277 (7) | 0.0257 (7) | 0.0334 (8) | 0.0052 (6) | 0.0043 (6) | −0.0024 (6) |
C121 | 0.0267 (10) | 0.0395 (12) | 0.0353 (12) | 0.0055 (9) | 0.0077 (9) | 0.0008 (10) |
C13 | 0.0409 (12) | 0.0160 (9) | 0.0339 (11) | 0.0018 (9) | −0.0018 (9) | 0.0000 (8) |
O14 | 0.0370 (8) | 0.0258 (7) | 0.0296 (8) | −0.0098 (6) | 0.0050 (7) | 0.0008 (6) |
C51 | 0.0220 (9) | 0.0259 (10) | 0.0205 (9) | −0.0016 (8) | −0.0009 (7) | 0.0024 (7) |
O51 | 0.0277 (7) | 0.0248 (7) | 0.0281 (7) | 0.0016 (6) | 0.0010 (6) | −0.0040 (6) |
N16 | 0.0221 (8) | 0.0188 (7) | 0.0236 (8) | −0.0025 (6) | 0.0016 (6) | −0.0007 (6) |
C21 | 0.0206 (9) | 0.0205 (9) | 0.0221 (9) | −0.0017 (7) | 0.0004 (7) | 0.0006 (7) |
C22 | 0.0218 (9) | 0.0195 (8) | 0.0224 (9) | 0.0000 (7) | −0.0003 (8) | 0.0006 (7) |
C23 | 0.0254 (9) | 0.0160 (8) | 0.0211 (9) | −0.0009 (7) | 0.0007 (8) | −0.0014 (7) |
C24 | 0.0221 (9) | 0.0223 (9) | 0.0230 (9) | −0.0041 (7) | 0.0039 (8) | 0.0005 (8) |
C25 | 0.0211 (9) | 0.0234 (9) | 0.0313 (10) | −0.0015 (7) | 0.0016 (8) | 0.0040 (8) |
O26 | 0.0214 (6) | 0.0244 (7) | 0.0280 (7) | −0.0020 (6) | −0.0008 (6) | 0.0065 (6) |
O22 | 0.0214 (6) | 0.0247 (7) | 0.0269 (7) | 0.0002 (5) | −0.0005 (6) | −0.0001 (6) |
C221 | 0.0242 (10) | 0.0202 (9) | 0.0388 (12) | 0.0014 (8) | 0.0044 (9) | −0.0002 (9) |
O221 | 0.0343 (8) | 0.0411 (9) | 0.0380 (9) | 0.0081 (7) | 0.0120 (7) | 0.0045 (7) |
C222 | 0.0253 (11) | 0.0385 (12) | 0.0510 (15) | 0.0052 (9) | −0.0019 (10) | −0.0018 (11) |
O23 | 0.0332 (7) | 0.0175 (6) | 0.0206 (7) | −0.0007 (5) | 0.0005 (6) | 0.0007 (5) |
C231 | 0.0307 (10) | 0.0285 (10) | 0.0254 (10) | 0.0086 (9) | 0.0022 (8) | 0.0032 (8) |
O231 | 0.0688 (12) | 0.0439 (9) | 0.0227 (8) | 0.0301 (9) | −0.0047 (8) | −0.0021 (7) |
C232 | 0.0746 (18) | 0.0262 (11) | 0.0353 (12) | 0.0105 (12) | −0.0039 (13) | 0.0051 (10) |
O24 | 0.0260 (7) | 0.0230 (7) | 0.0262 (7) | −0.0060 (5) | 0.0051 (6) | −0.0016 (6) |
C241 | 0.0216 (9) | 0.0310 (10) | 0.0357 (12) | −0.0047 (8) | 0.0034 (8) | −0.0064 (9) |
O241 | 0.0450 (10) | 0.0715 (13) | 0.0406 (10) | −0.0319 (10) | 0.0149 (8) | −0.0264 (9) |
C242 | 0.0366 (12) | 0.0310 (11) | 0.0436 (13) | −0.0134 (10) | 0.0062 (10) | −0.0011 (10) |
N31 | 0.0223 (8) | 0.0219 (8) | 0.0228 (8) | −0.0030 (6) | 0.0019 (7) | 0.0011 (6) |
C32 | 0.0209 (9) | 0.0252 (9) | 0.0227 (9) | −0.0014 (7) | −0.0002 (7) | 0.0010 (7) |
N33 | 0.0238 (8) | 0.0211 (8) | 0.0257 (9) | −0.0037 (6) | −0.0004 (7) | 0.0037 (6) |
C34 | 0.0206 (9) | 0.0280 (10) | 0.0220 (9) | −0.0037 (8) | −0.0038 (7) | 0.0053 (8) |
C35 | 0.0205 (9) | 0.0263 (9) | 0.0225 (9) | −0.0033 (8) | −0.0020 (8) | 0.0032 (8) |
C36 | 0.0202 (9) | 0.0232 (9) | 0.0184 (9) | −0.0024 (7) | −0.0024 (7) | 0.0011 (7) |
O32 | 0.0289 (7) | 0.0241 (7) | 0.0359 (8) | −0.0008 (6) | 0.0086 (6) | −0.0008 (6) |
C321 | 0.0329 (11) | 0.0331 (11) | 0.0419 (13) | −0.0036 (9) | 0.0151 (10) | −0.0024 (10) |
C33 | 0.0354 (11) | 0.0218 (10) | 0.0477 (14) | −0.0029 (9) | 0.0038 (10) | 0.0038 (9) |
O34 | 0.0287 (7) | 0.0307 (8) | 0.0343 (8) | −0.0086 (6) | 0.0035 (6) | 0.0097 (6) |
C53 | 0.0232 (10) | 0.0326 (11) | 0.0232 (10) | −0.0029 (8) | 0.0003 (8) | 0.0045 (8) |
O53 | 0.0271 (7) | 0.0340 (8) | 0.0315 (8) | 0.0016 (6) | 0.0033 (6) | −0.0002 (6) |
N36 | 0.0223 (8) | 0.0227 (8) | 0.0263 (9) | 0.0005 (6) | 0.0035 (7) | 0.0008 (7) |
C41 | 0.0207 (9) | 0.0229 (9) | 0.0232 (10) | −0.0008 (7) | 0.0001 (8) | 0.0017 (7) |
C42 | 0.0203 (9) | 0.0233 (9) | 0.0221 (9) | −0.0001 (7) | −0.0025 (7) | −0.0013 (8) |
C43 | 0.0221 (9) | 0.0185 (8) | 0.0212 (9) | 0.0030 (7) | −0.0008 (7) | 0.0006 (7) |
C44 | 0.0203 (9) | 0.0219 (9) | 0.0220 (9) | −0.0016 (7) | 0.0021 (7) | 0.0020 (7) |
C45 | 0.0190 (9) | 0.0283 (10) | 0.0312 (11) | 0.0002 (8) | 0.0012 (8) | 0.0074 (9) |
O46 | 0.0201 (6) | 0.0286 (7) | 0.0267 (7) | −0.0037 (6) | −0.0027 (6) | 0.0063 (6) |
O42 | 0.0203 (6) | 0.0312 (7) | 0.0261 (7) | −0.0025 (6) | −0.0029 (6) | −0.0008 (6) |
C421 | 0.0221 (9) | 0.0272 (10) | 0.0369 (12) | 0.0011 (8) | −0.0020 (9) | 0.0056 (9) |
O421 | 0.0255 (8) | 0.0589 (11) | 0.0430 (10) | −0.0004 (7) | 0.0039 (7) | −0.0091 (9) |
C422 | 0.0269 (11) | 0.0461 (13) | 0.0436 (13) | −0.0027 (10) | −0.0106 (10) | 0.0087 (11) |
O43 | 0.0291 (7) | 0.0204 (6) | 0.0214 (7) | 0.0042 (6) | 0.0008 (6) | 0.0031 (5) |
C431 | 0.0237 (9) | 0.0289 (10) | 0.0252 (10) | 0.0016 (8) | −0.0028 (8) | 0.0053 (8) |
O432 | 0.0512 (10) | 0.0420 (9) | 0.0223 (8) | 0.0132 (8) | −0.0023 (7) | 0.0017 (7) |
C432 | 0.0513 (14) | 0.0282 (11) | 0.0354 (12) | 0.0019 (10) | −0.0056 (11) | 0.0092 (9) |
O44 | 0.0259 (7) | 0.0242 (7) | 0.0245 (7) | −0.0053 (6) | 0.0047 (6) | −0.0009 (6) |
C441 | 0.0270 (10) | 0.0273 (10) | 0.0346 (12) | −0.0058 (9) | 0.0035 (8) | −0.0020 (9) |
O441 | 0.0566 (11) | 0.0799 (14) | 0.0338 (10) | −0.0407 (11) | 0.0010 (8) | −0.0073 (10) |
C442 | 0.0397 (13) | 0.0329 (11) | 0.0400 (13) | −0.0124 (10) | 0.0121 (10) | −0.0047 (10) |
Geometric parameters (Å, º) top
N11—C12 | 1.304 (2) | C32—N33 | 1.352 (2) |
C12—N13 | 1.351 (3) | N33—C34 | 1.417 (3) |
N13—C14 | 1.413 (2) | C34—C35 | 1.437 (3) |
C14—C15 | 1.439 (3) | C35—C36 | 1.405 (3) |
C15—C16 | 1.411 (3) | C36—N31 | 1.364 (2) |
C16—N11 | 1.362 (2) | C32—O32 | 1.325 (2) |
C12—O12 | 1.328 (2) | N33—C33 | 1.468 (3) |
N13—C13 | 1.471 (2) | C34—O34 | 1.226 (2) |
C14—O14 | 1.223 (2) | C35—C53 | 1.432 (3) |
C15—C51 | 1.432 (3) | C53—O53 | 1.232 (3) |
C51—O51 | 1.241 (2) | C36—N36 | 1.350 (2) |
C16—N16 | 1.345 (2) | O32—C321 | 1.453 (2) |
O12—C121 | 1.451 (3) | C321—H32A | 0.9800 |
C121—H12A | 0.9800 | C321—H32B | 0.9800 |
C121—H12B | 0.9800 | C321—H32C | 0.9800 |
C121—H12C | 0.9800 | C33—H33A | 0.9800 |
C13—H13A | 0.9800 | C33—H33B | 0.9800 |
C13—H13B | 0.9800 | C33—H33C | 0.9800 |
C13—H13C | 0.9800 | C53—H53 | 0.9500 |
C51—H51 | 0.9500 | N36—C41 | 1.434 (2) |
N16—C21 | 1.435 (2) | N36—H36 | 0.8800 |
N16—H16 | 0.8800 | C41—O46 | 1.428 (2) |
C21—O26 | 1.426 (2) | C41—C42 | 1.536 (3) |
C21—C22 | 1.535 (3) | C41—H41 | 1.0000 |
C21—H21 | 1.0000 | C42—O42 | 1.446 (2) |
C22—O22 | 1.437 (2) | C42—C43 | 1.514 (3) |
C22—C23 | 1.512 (3) | C42—H42 | 1.0000 |
C22—H22 | 1.0000 | C43—O43 | 1.444 (2) |
C23—O23 | 1.448 (2) | C43—C44 | 1.517 (3) |
C23—C24 | 1.515 (3) | C43—H43 | 1.0000 |
C23—H23 | 1.0000 | C44—O44 | 1.444 (2) |
C24—O24 | 1.448 (2) | C44—C45 | 1.524 (3) |
C24—C25 | 1.524 (3) | C44—H44 | 1.0000 |
C24—H24 | 1.0000 | C45—O46 | 1.442 (2) |
C25—O26 | 1.433 (2) | C45—H45A | 0.9900 |
C25—H25A | 0.9900 | C45—H45B | 0.9900 |
C25—H25B | 0.9900 | O42—C421 | 1.351 (2) |
O22—C221 | 1.356 (2) | C421—O421 | 1.198 (3) |
C221—O221 | 1.205 (3) | C421—C422 | 1.499 (3) |
C221—C222 | 1.494 (3) | C422—H42A | 0.9800 |
C222—H22A | 0.9800 | C422—H42B | 0.9800 |
C222—H22B | 0.9800 | C422—H42C | 0.9800 |
C222—H22C | 0.9800 | O43—C431 | 1.347 (2) |
O23—C231 | 1.351 (2) | C431—O432 | 1.201 (3) |
C231—O231 | 1.192 (3) | C431—C432 | 1.499 (3) |
C231—C232 | 1.491 (3) | C432—H43A | 0.9800 |
C232—H23A | 0.9800 | C432—H43B | 0.9800 |
C232—H23B | 0.9800 | C432—H43C | 0.9800 |
C232—H23C | 0.9800 | O44—C441 | 1.343 (2) |
O24—C241 | 1.351 (2) | C441—O441 | 1.196 (3) |
C241—O241 | 1.196 (3) | C441—C442 | 1.487 (3) |
C241—C242 | 1.489 (3) | C442—H44A | 0.9800 |
C242—H24A | 0.9800 | C442—H44B | 0.9800 |
C242—H24B | 0.9800 | C442—H44C | 0.9800 |
C242—H24C | 0.9800 | O61—H61 | 0.839 (11) |
N31—C32 | 1.303 (2) | O61—H62 | 0.840 (11) |
| | | |
C12—N11—C16 | 116.12 (17) | N31—C32—O32 | 121.00 (17) |
N11—C12—O12 | 120.39 (18) | N31—C32—N33 | 126.42 (18) |
N11—C12—N13 | 126.81 (18) | O32—C32—N33 | 112.56 (16) |
O12—C12—N13 | 112.80 (16) | C32—N33—C34 | 120.05 (16) |
C12—N13—C14 | 120.28 (15) | C32—N33—C33 | 120.71 (18) |
C12—N13—C13 | 121.07 (17) | C34—N33—C33 | 119.24 (17) |
C14—N13—C13 | 118.63 (17) | O34—C34—N33 | 119.07 (18) |
O14—C14—N13 | 119.33 (17) | O34—C34—C35 | 125.8 (2) |
O14—C14—C15 | 125.86 (19) | N33—C34—C35 | 115.10 (17) |
N13—C14—C15 | 114.81 (16) | C36—C35—C53 | 123.19 (18) |
C16—C15—C51 | 123.55 (17) | C36—C35—C34 | 118.97 (18) |
C16—C15—C14 | 118.92 (17) | C53—C35—C34 | 117.81 (17) |
C51—C15—C14 | 117.48 (17) | N36—C36—N31 | 116.38 (17) |
N16—C16—N11 | 116.73 (17) | N36—C36—C35 | 120.90 (18) |
N16—C16—C15 | 120.38 (18) | N31—C36—C35 | 122.72 (17) |
N11—C16—C15 | 122.89 (16) | C32—O32—C321 | 117.04 (16) |
C12—O12—C121 | 116.99 (16) | O32—C321—H32A | 109.5 |
O12—C121—H12A | 109.5 | O32—C321—H32B | 109.5 |
O12—C121—H12B | 109.5 | H32A—C321—H32B | 109.5 |
H12A—C121—H12B | 109.5 | O32—C321—H32C | 109.5 |
O12—C121—H12C | 109.5 | H32A—C321—H32C | 109.5 |
H12A—C121—H12C | 109.5 | H32B—C321—H32C | 109.5 |
H12B—C121—H12C | 109.5 | N33—C33—H33A | 109.5 |
N13—C13—H13A | 109.5 | N33—C33—H33B | 109.5 |
N13—C13—H13B | 109.5 | H33A—C33—H33B | 109.5 |
H13A—C13—H13B | 109.5 | N33—C33—H33C | 109.5 |
N13—C13—H13C | 109.5 | H33A—C33—H33C | 109.5 |
H13A—C13—H13C | 109.5 | H33B—C33—H33C | 109.5 |
H13B—C13—H13C | 109.5 | O53—C53—C35 | 126.08 (18) |
O51—C51—C15 | 124.87 (18) | O53—C53—H53 | 117.0 |
O51—C51—H51 | 117.6 | C35—C53—H53 | 117.0 |
C15—C51—H51 | 117.6 | C36—N36—C41 | 122.44 (17) |
C16—N16—C21 | 123.04 (17) | C36—N36—H36 | 118.8 |
C16—N16—H16 | 118.5 | C41—N36—H36 | 118.8 |
C21—N16—H16 | 118.5 | O46—C41—N36 | 108.48 (15) |
O26—C21—N16 | 107.59 (15) | O46—C41—C42 | 108.91 (15) |
O26—C21—C22 | 109.34 (15) | N36—C41—C42 | 111.39 (15) |
N16—C21—C22 | 109.05 (15) | O46—C41—H41 | 109.3 |
O26—C21—H21 | 110.3 | N36—C41—H41 | 109.3 |
N16—C21—H21 | 110.3 | C42—C41—H41 | 109.3 |
C22—C21—H21 | 110.3 | O42—C42—C43 | 106.63 (15) |
O22—C22—C23 | 107.24 (15) | O42—C42—C41 | 108.38 (15) |
O22—C22—C21 | 109.71 (15) | C43—C42—C41 | 108.42 (15) |
C23—C22—C21 | 109.69 (15) | O42—C42—H42 | 111.1 |
O22—C22—H22 | 110.0 | C43—C42—H42 | 111.1 |
C23—C22—H22 | 110.0 | C41—C42—H42 | 111.1 |
C21—C22—H22 | 110.0 | O43—C43—C42 | 109.25 (15) |
O23—C23—C22 | 108.79 (15) | O43—C43—C44 | 107.33 (15) |
O23—C23—C24 | 107.43 (15) | C42—C43—C44 | 110.85 (15) |
C22—C23—C24 | 110.34 (15) | O43—C43—H43 | 109.8 |
O23—C23—H23 | 110.1 | C42—C43—H43 | 109.8 |
C22—C23—H23 | 110.1 | C44—C43—H43 | 109.8 |
C24—C23—H23 | 110.1 | O44—C44—C43 | 105.15 (15) |
O24—C24—C23 | 107.10 (15) | O44—C44—C45 | 110.77 (15) |
O24—C24—C25 | 109.61 (16) | C43—C44—C45 | 110.51 (15) |
C23—C24—C25 | 108.77 (16) | O44—C44—H44 | 110.1 |
O24—C24—H24 | 110.4 | C43—C44—H44 | 110.1 |
C23—C24—H24 | 110.4 | C45—C44—H44 | 110.1 |
C25—C24—H24 | 110.4 | O46—C45—C44 | 108.60 (15) |
O26—C25—C24 | 107.94 (16) | O46—C45—H45A | 110.0 |
O26—C25—H25A | 110.1 | C44—C45—H45A | 110.0 |
C24—C25—H25A | 110.1 | O46—C45—H45B | 110.0 |
O26—C25—H25B | 110.1 | C44—C45—H45B | 110.0 |
C24—C25—H25B | 110.1 | H45A—C45—H45B | 108.4 |
H25A—C25—H25B | 108.4 | C41—O46—C45 | 110.58 (14) |
C21—O26—C25 | 111.83 (14) | C421—O42—C42 | 118.11 (15) |
C221—O22—C22 | 117.61 (15) | O421—C421—O42 | 123.38 (19) |
O221—C221—O22 | 123.2 (2) | O421—C421—C422 | 125.4 (2) |
O221—C221—C222 | 125.5 (2) | O42—C421—C422 | 111.23 (19) |
O22—C221—C222 | 111.35 (18) | C421—C422—H42A | 109.5 |
C221—C222—H22A | 109.5 | C421—C422—H42B | 109.5 |
C221—C222—H22B | 109.5 | H42A—C422—H42B | 109.5 |
H22A—C222—H22B | 109.5 | C421—C422—H42C | 109.5 |
C221—C222—H22C | 109.5 | H42A—C422—H42C | 109.5 |
H22A—C222—H22C | 109.5 | H42B—C422—H42C | 109.5 |
H22B—C222—H22C | 109.5 | C431—O43—C43 | 117.72 (15) |
C231—O23—C23 | 117.80 (15) | O432—C431—O43 | 124.43 (18) |
O231—C231—O23 | 124.01 (19) | O432—C431—C432 | 125.5 (2) |
O231—C231—C232 | 125.3 (2) | O43—C431—C432 | 110.09 (18) |
O23—C231—C232 | 110.72 (18) | C431—C432—H43A | 109.5 |
C231—C232—H23A | 109.5 | C431—C432—H43B | 109.5 |
C231—C232—H23B | 109.5 | H43A—C432—H43B | 109.5 |
H23A—C232—H23B | 109.5 | C431—C432—H43C | 109.5 |
C231—C232—H23C | 109.5 | H43A—C432—H43C | 109.5 |
H23A—C232—H23C | 109.5 | H43B—C432—H43C | 109.5 |
H23B—C232—H23C | 109.5 | C441—O44—C44 | 117.49 (15) |
C241—O24—C24 | 117.37 (15) | O441—C441—O44 | 123.2 (2) |
O241—C241—O24 | 123.7 (2) | O441—C441—C442 | 125.4 (2) |
O241—C241—C242 | 124.8 (2) | O44—C441—C442 | 111.33 (18) |
O24—C241—C242 | 111.50 (18) | C441—C442—H44A | 109.5 |
C241—C242—H24A | 109.5 | C441—C442—H44B | 109.5 |
C241—C242—H24B | 109.5 | H44A—C442—H44B | 109.5 |
H24A—C242—H24B | 109.5 | C441—C442—H44C | 109.5 |
C241—C242—H24C | 109.5 | H44A—C442—H44C | 109.5 |
H24A—C242—H24C | 109.5 | H44B—C442—H44C | 109.5 |
H24B—C242—H24C | 109.5 | H61—O61—H62 | 106.0 (18) |
C32—N31—C36 | 116.60 (16) | | |
| | | |
C16—N11—C12—O12 | −178.30 (16) | C36—N31—C32—O32 | −177.81 (17) |
C16—N11—C12—N13 | 2.0 (3) | C36—N31—C32—N33 | 0.3 (3) |
N11—C12—N13—C14 | −1.9 (3) | N31—C32—N33—C34 | −3.2 (3) |
O12—C12—N13—C14 | 178.47 (16) | O32—C32—N33—C34 | 175.03 (16) |
N11—C12—N13—C13 | 179.44 (19) | N31—C32—N33—C33 | 176.5 (2) |
O12—C12—N13—C13 | −0.2 (3) | O32—C32—N33—C33 | −5.2 (3) |
C12—N13—C14—O14 | 179.10 (18) | C32—N33—C34—O34 | −176.75 (18) |
C13—N13—C14—O14 | −2.2 (3) | C33—N33—C34—O34 | 3.5 (3) |
C12—N13—C14—C15 | −1.5 (2) | C32—N33—C34—C35 | 2.7 (3) |
C13—N13—C14—C15 | 177.27 (17) | C33—N33—C34—C35 | −177.00 (19) |
O14—C14—C15—C16 | −176.34 (18) | O34—C34—C35—C36 | 179.66 (18) |
N13—C14—C15—C16 | 4.3 (2) | N33—C34—C35—C36 | 0.2 (3) |
O14—C14—C15—C51 | 6.1 (3) | O34—C34—C35—C53 | 1.7 (3) |
N13—C14—C15—C51 | −173.29 (16) | N33—C34—C35—C53 | −177.73 (16) |
C12—N11—C16—N16 | −179.74 (17) | C32—N31—C36—N36 | −177.29 (18) |
C12—N11—C16—C15 | 1.2 (3) | C32—N31—C36—C35 | 2.9 (3) |
C51—C15—C16—N16 | −6.0 (3) | C53—C35—C36—N36 | −5.1 (3) |
C14—C15—C16—N16 | 176.58 (17) | C34—C35—C36—N36 | 177.08 (18) |
C51—C15—C16—N11 | 173.04 (17) | C53—C35—C36—N31 | 174.69 (17) |
C14—C15—C16—N11 | −4.4 (3) | C34—C35—C36—N31 | −3.2 (3) |
N11—C12—O12—C121 | 5.9 (3) | N31—C32—O32—C321 | 2.6 (3) |
N13—C12—O12—C121 | −174.44 (16) | N33—C32—O32—C321 | −175.78 (17) |
C16—C15—C51—O51 | −0.5 (3) | C36—C35—C53—O53 | 1.4 (3) |
C14—C15—C51—O51 | 176.94 (19) | C34—C35—C53—O53 | 179.2 (2) |
N11—C16—N16—C21 | 0.3 (3) | N31—C36—N36—C41 | −0.2 (3) |
C15—C16—N16—C21 | 179.43 (17) | C35—C36—N36—C41 | 179.60 (17) |
C16—N16—C21—O26 | −79.7 (2) | C36—N36—C41—O46 | −92.8 (2) |
C16—N16—C21—C22 | 161.82 (17) | C36—N36—C41—C42 | 147.33 (18) |
O26—C21—C22—O22 | 173.52 (14) | O46—C41—C42—O42 | 175.52 (14) |
N16—C21—C22—O22 | −69.08 (19) | N36—C41—C42—O42 | −64.9 (2) |
O26—C21—C22—C23 | 56.0 (2) | O46—C41—C42—C43 | 60.14 (19) |
N16—C21—C22—C23 | 173.36 (15) | N36—C41—C42—C43 | 179.75 (15) |
O22—C22—C23—O23 | 69.56 (18) | O42—C42—C43—O43 | 71.68 (18) |
C21—C22—C23—O23 | −171.35 (15) | C41—C42—C43—O43 | −171.81 (14) |
O22—C22—C23—C24 | −172.82 (15) | O42—C42—C43—C44 | −170.24 (15) |
C21—C22—C23—C24 | −53.7 (2) | C41—C42—C43—C44 | −53.7 (2) |
O23—C23—C24—O24 | −66.78 (18) | O43—C43—C44—O44 | −68.13 (17) |
C22—C23—C24—O24 | 174.77 (15) | C42—C43—C44—O44 | 172.64 (14) |
O23—C23—C24—C25 | 174.83 (16) | O43—C43—C44—C45 | 172.30 (15) |
C22—C23—C24—C25 | 56.4 (2) | C42—C43—C44—C45 | 53.1 (2) |
O24—C24—C25—O26 | −177.61 (14) | O44—C44—C45—O46 | −172.96 (15) |
C23—C24—C25—O26 | −60.8 (2) | C43—C44—C45—O46 | −56.8 (2) |
N16—C21—O26—C25 | 178.25 (14) | N36—C41—O46—C45 | 171.58 (14) |
C22—C21—O26—C25 | −63.43 (19) | C42—C41—O46—C45 | −67.01 (19) |
C24—C25—O26—C21 | 65.9 (2) | C44—C45—O46—C41 | 64.8 (2) |
C23—C22—O22—C221 | −138.99 (16) | C43—C42—O42—C421 | −138.41 (17) |
C21—C22—O22—C221 | 101.93 (19) | C41—C42—O42—C421 | 105.05 (19) |
C22—O22—C221—O221 | −4.1 (3) | C42—O42—C421—O421 | −0.9 (3) |
C22—O22—C221—C222 | 175.25 (17) | C42—O42—C421—C422 | −179.22 (17) |
C22—C23—O23—C231 | −116.71 (18) | C42—C43—O43—C431 | −127.34 (18) |
C24—C23—O23—C231 | 123.84 (18) | C44—C43—O43—C431 | 112.41 (18) |
C23—O23—C231—O231 | 7.7 (3) | C43—O43—C431—O432 | 11.4 (3) |
C23—O23—C231—C232 | −173.46 (19) | C43—O43—C431—C432 | −168.84 (17) |
C23—C24—O24—C241 | 112.56 (18) | C43—C44—O44—C441 | 146.39 (17) |
C25—C24—O24—C241 | −129.59 (19) | C45—C44—O44—C441 | −94.2 (2) |
C24—O24—C241—O241 | 7.8 (3) | C44—O44—C441—O441 | 8.2 (3) |
C24—O24—C241—C242 | −171.66 (17) | C44—O44—C441—C442 | −172.60 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N16—H16···O51 | 0.88 | 2.03 | 2.707 (2) | 133 |
N36—H36···O53 | 0.88 | 2.06 | 2.725 (2) | 132 |
C24—H24···O14i | 1.00 | 2.34 | 3.237 (3) | 148 |
C44—H44···O231 | 1.00 | 2.28 | 3.213 (3) | 155 |
C45—H45B···O34ii | 0.99 | 2.38 | 3.245 (3) | 145 |
C51—H51···O241iii | 0.95 | 2.54 | 3.442 (3) | 159 |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x+1/2, −y+1/2, −z+1; (iii) −x+1, y−1/2, −z+3/2. |
(II) 2-methylsulfanyl-6-oxo-4-(2,3,4-tri-
O-acetyl-
β-D-xylopyranosylamino)-1,6-dihydropyrimidine-5-carbaldehyde
top
Crystal data top
C17H21N3O9S | F(000) = 928 |
Mr = 443.44 | Dx = 1.494 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4481 reflections |
a = 6.9294 (1) Å | θ = 3.3–27.5° |
b = 10.7415 (2) Å | µ = 0.22 mm−1 |
c = 26.4825 (5) Å | T = 120 K |
V = 1971.15 (6) Å3 | Block, colourless |
Z = 4 | 0.44 × 0.35 × 0.30 mm |
Data collection top
Bruker–Nonius KappaCCD diffractometer | 4482 independent reflections |
Radiation source: Bruker–Nonius FR591 rotating anode | 4065 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.3° |
ϕ and ω scans | h = −8→6 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | k = −13→9 |
Tmin = 0.885, Tmax = 0.936 | l = −34→34 |
12812 measured reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.038 | w = 1/[σ2(Fo2) + (0.0577P)2 + 0.0098P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.096 | (Δ/σ)max = 0.001 |
S = 1.14 | Δρmax = 0.42 e Å−3 |
4482 reflections | Δρmin = −0.45 e Å−3 |
327 parameters | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
40 restraints | Extinction coefficient: 0.039 (2) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.02 (7) |
Crystal data top
C17H21N3O9S | V = 1971.15 (6) Å3 |
Mr = 443.44 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 6.9294 (1) Å | µ = 0.22 mm−1 |
b = 10.7415 (2) Å | T = 120 K |
c = 26.4825 (5) Å | 0.44 × 0.35 × 0.30 mm |
Data collection top
Bruker–Nonius KappaCCD diffractometer | 4482 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 4065 reflections with I > 2σ(I) |
Tmin = 0.885, Tmax = 0.936 | Rint = 0.031 |
12812 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.096 | Δρmax = 0.42 e Å−3 |
S = 1.14 | Δρmin = −0.45 e Å−3 |
4482 reflections | Absolute structure: Flack (1983) |
327 parameters | Absolute structure parameter: −0.02 (7) |
40 restraints | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
N11A | 0.2117 (3) | 0.88401 (15) | 0.69071 (6) | 0.0192 (4) | 0.899 (2) |
C12A | 0.2137 (3) | 0.98938 (18) | 0.71673 (8) | 0.0183 (4) | 0.899 (2) |
N13A | 0.2512 (3) | 0.99686 (15) | 0.76673 (6) | 0.0197 (4) | 0.899 (2) |
H13A | 0.2444 | 1.0701 | 0.7815 | 0.024* | 0.899 (2) |
C14A | 0.3007 (4) | 0.89276 (19) | 0.79600 (7) | 0.0194 (4) | 0.899 (2) |
C15A | 0.2951 (7) | 0.7777 (2) | 0.76919 (9) | 0.0192 (6) | 0.899 (2) |
C16A | 0.2517 (5) | 0.77804 (18) | 0.71710 (9) | 0.0175 (6) | 0.899 (2) |
S1A | 0.16492 (8) | 1.12014 (5) | 0.67968 (2) | 0.02615 (19) | 0.899 (2) |
C17A | 0.1898 (3) | 1.25098 (19) | 0.72224 (8) | 0.0275 (5) | 0.899 (2) |
H17A | 0.1052 | 1.2390 | 0.7515 | 0.041* | 0.899 (2) |
H17B | 0.1538 | 1.3278 | 0.7046 | 0.041* | 0.899 (2) |
H17C | 0.3241 | 1.2570 | 0.7336 | 0.041* | 0.899 (2) |
O14A | 0.3420 (3) | 0.90748 (14) | 0.84079 (6) | 0.0273 (4) | 0.899 (2) |
C51A | 0.3352 (4) | 0.6648 (2) | 0.79630 (8) | 0.0207 (5) | 0.899 (2) |
H51A | 0.3549 | 0.6721 | 0.8317 | 0.025* | 0.899 (2) |
O51A | 0.3465 (9) | 0.55923 (17) | 0.77805 (12) | 0.0241 (4) | 0.899 (2) |
N16A | 0.2544 (6) | 0.6701 (3) | 0.6922 (2) | 0.0207 (7) | 0.899 (2) |
H16A | 0.2887 | 0.6038 | 0.7095 | 0.025* | 0.899 (2) |
N11B | 0.226 (4) | 0.9040 (8) | 0.7040 (4) | 0.0192 (4) | 0.101 (2) |
C12B | 0.229 (3) | 0.9958 (7) | 0.7374 (3) | 0.0183 (4) | 0.101 (2) |
N13B | 0.253 (3) | 0.9795 (8) | 0.7876 (3) | 0.0197 (4) | 0.101 (2) |
H13B | 0.2313 | 1.0428 | 0.8078 | 0.024* | 0.101 (2) |
C14B | 0.312 (4) | 0.8664 (10) | 0.8087 (4) | 0.0194 (4) | 0.101 (2) |
C15B | 0.323 (8) | 0.7666 (12) | 0.7733 (5) | 0.0192 (6) | 0.101 (2) |
C16B | 0.281 (7) | 0.7897 (11) | 0.7219 (5) | 0.0175 (6) | 0.101 (2) |
S1B | 0.1630 (7) | 1.1402 (4) | 0.71288 (19) | 0.0254 (15) | 0.101 (2) |
C17B | 0.158 (3) | 1.1174 (12) | 0.6450 (2) | 0.026 (4) | 0.101 (2) |
H17D | 0.0794 | 1.0439 | 0.6371 | 0.039* | 0.101 (2) |
H17E | 0.2892 | 1.1050 | 0.6325 | 0.039* | 0.101 (2) |
H17F | 0.1010 | 1.1908 | 0.6288 | 0.039* | 0.101 (2) |
O14B | 0.363 (3) | 0.8653 (12) | 0.8531 (4) | 0.0273 (4) | 0.101 (2) |
C51B | 0.371 (5) | 0.6449 (9) | 0.7916 (6) | 0.0207 (5) | 0.101 (2) |
H51B | 0.4376 | 0.6412 | 0.8230 | 0.025* | 0.101 (2) |
O51B | 0.337 (9) | 0.5446 (11) | 0.7709 (14) | 0.0241 (4) | 0.101 (2) |
N16B | 0.228 (7) | 0.687 (4) | 0.693 (2) | 0.0207 (7) | 0.101 (2) |
H16B | 0.1983 | 0.6237 | 0.7126 | 0.025* | 0.101 (2) |
C21 | 0.2073 (3) | 0.65075 (16) | 0.63997 (6) | 0.0206 (4) | |
H21 | 0.1307 | 0.7222 | 0.6264 | 0.025* | |
C22 | 0.3924 (3) | 0.63106 (15) | 0.60911 (6) | 0.0182 (4) | |
H22 | 0.4797 | 0.5703 | 0.6264 | 0.022* | |
C23 | 0.3431 (2) | 0.58661 (15) | 0.55639 (6) | 0.0179 (3) | |
H23 | 0.2763 | 0.6542 | 0.5372 | 0.022* | |
C24 | 0.2143 (3) | 0.47314 (16) | 0.56016 (6) | 0.0196 (4) | |
H24 | 0.2856 | 0.4039 | 0.5771 | 0.024* | |
C25 | 0.0354 (2) | 0.50570 (18) | 0.59043 (6) | 0.0222 (4) | |
H25A | −0.0340 | 0.5758 | 0.5743 | 0.027* | |
H25B | −0.0527 | 0.4332 | 0.5920 | 0.027* | |
O26 | 0.09607 (18) | 0.54000 (12) | 0.64029 (4) | 0.0231 (3) | |
O22 | 0.48698 (18) | 0.75006 (11) | 0.60321 (4) | 0.0203 (3) | |
C221 | 0.6450 (3) | 0.77542 (17) | 0.63151 (7) | 0.0230 (4) | |
O221 | 0.7116 (2) | 0.70511 (13) | 0.66180 (6) | 0.0379 (4) | |
C222 | 0.7170 (3) | 0.90289 (16) | 0.62015 (7) | 0.0282 (4) | |
H22A | 0.6377 | 0.9643 | 0.6380 | 0.042* | |
H22B | 0.7094 | 0.9180 | 0.5837 | 0.042* | |
H22C | 0.8514 | 0.9104 | 0.6313 | 0.042* | |
O23 | 0.51873 (17) | 0.55138 (11) | 0.53106 (4) | 0.0205 (3) | |
C231 | 0.5649 (3) | 0.61331 (17) | 0.48826 (6) | 0.0203 (4) | |
O231 | 0.4777 (2) | 0.70263 (12) | 0.47298 (5) | 0.0283 (3) | |
C232 | 0.7360 (3) | 0.55551 (18) | 0.46332 (7) | 0.0289 (4) | |
H23A | 0.7338 | 0.5745 | 0.4271 | 0.043* | |
H23B | 0.7322 | 0.4651 | 0.4681 | 0.043* | |
H23C | 0.8545 | 0.5890 | 0.4783 | 0.043* | |
O24 | 0.16847 (18) | 0.43814 (12) | 0.50885 (4) | 0.0213 (3) | |
C241 | 0.1315 (3) | 0.31614 (18) | 0.50083 (7) | 0.0242 (4) | |
O241 | 0.1123 (2) | 0.24259 (12) | 0.53471 (5) | 0.0364 (4) | |
C242 | 0.1192 (3) | 0.28741 (19) | 0.44560 (7) | 0.0284 (4) | |
H24A | 0.1050 | 0.1974 | 0.4409 | 0.043* | |
H24B | 0.2370 | 0.3159 | 0.4287 | 0.043* | |
H24C | 0.0073 | 0.3302 | 0.4310 | 0.043* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N11A | 0.0203 (8) | 0.0205 (8) | 0.0169 (9) | −0.0021 (8) | −0.0017 (8) | −0.0022 (7) |
C12A | 0.0148 (9) | 0.0200 (9) | 0.0202 (10) | −0.0016 (8) | 0.0005 (9) | −0.0040 (8) |
N13A | 0.0227 (8) | 0.0198 (8) | 0.0165 (9) | 0.0006 (7) | 0.0000 (9) | −0.0031 (7) |
C14A | 0.0181 (9) | 0.0210 (11) | 0.0190 (10) | −0.0004 (9) | 0.0021 (10) | −0.0001 (8) |
C15A | 0.014 (2) | 0.0233 (10) | 0.0205 (9) | 0.0006 (8) | 0.0015 (8) | −0.0009 (8) |
C16A | 0.0127 (17) | 0.0190 (9) | 0.0210 (8) | −0.0028 (9) | 0.0003 (8) | −0.0022 (7) |
S1A | 0.0284 (3) | 0.0221 (3) | 0.0279 (4) | 0.0005 (2) | −0.0055 (2) | 0.0027 (2) |
C17A | 0.0233 (10) | 0.0214 (10) | 0.0378 (12) | 0.0001 (9) | −0.0029 (9) | 0.0005 (9) |
O14A | 0.0369 (9) | 0.0255 (9) | 0.0195 (8) | 0.0000 (8) | −0.0038 (7) | −0.0025 (6) |
C51A | 0.0174 (14) | 0.0289 (11) | 0.0158 (9) | 0.0030 (9) | 0.0043 (8) | −0.0016 (8) |
O51A | 0.0313 (10) | 0.0235 (8) | 0.0175 (13) | 0.0019 (11) | −0.0007 (11) | −0.0018 (7) |
N16A | 0.0288 (19) | 0.0175 (14) | 0.0158 (7) | 0.0057 (11) | 0.0002 (11) | 0.0011 (11) |
N11B | 0.0203 (8) | 0.0205 (8) | 0.0169 (9) | −0.0021 (8) | −0.0017 (8) | −0.0022 (7) |
C12B | 0.0148 (9) | 0.0200 (9) | 0.0202 (10) | −0.0016 (8) | 0.0005 (9) | −0.0040 (8) |
N13B | 0.0227 (8) | 0.0198 (8) | 0.0165 (9) | 0.0006 (7) | 0.0000 (9) | −0.0031 (7) |
C14B | 0.0181 (9) | 0.0210 (11) | 0.0190 (10) | −0.0004 (9) | 0.0021 (10) | −0.0001 (8) |
C15B | 0.014 (2) | 0.0233 (10) | 0.0205 (9) | 0.0006 (8) | 0.0015 (8) | −0.0009 (8) |
C16B | 0.0127 (17) | 0.0190 (9) | 0.0210 (8) | −0.0028 (9) | 0.0003 (8) | −0.0022 (7) |
S1B | 0.027 (2) | 0.027 (3) | 0.022 (3) | 0.007 (2) | −0.002 (2) | −0.0047 (19) |
C17B | 0.041 (8) | 0.030 (7) | 0.007 (6) | −0.002 (7) | −0.012 (6) | 0.003 (6) |
O14B | 0.0369 (9) | 0.0255 (9) | 0.0195 (8) | 0.0000 (8) | −0.0038 (7) | −0.0025 (6) |
C51B | 0.0174 (14) | 0.0289 (11) | 0.0158 (9) | 0.0030 (9) | 0.0043 (8) | −0.0016 (8) |
O51B | 0.0313 (10) | 0.0235 (8) | 0.0175 (13) | 0.0019 (11) | −0.0007 (11) | −0.0018 (7) |
N16B | 0.0288 (19) | 0.0175 (14) | 0.0158 (7) | 0.0057 (11) | 0.0002 (11) | 0.0011 (11) |
C21 | 0.0233 (9) | 0.0215 (9) | 0.0170 (8) | 0.0023 (7) | −0.0002 (7) | 0.0000 (7) |
C22 | 0.0225 (8) | 0.0135 (8) | 0.0187 (8) | 0.0001 (7) | −0.0010 (7) | 0.0014 (7) |
C23 | 0.0195 (8) | 0.0167 (8) | 0.0176 (8) | 0.0033 (7) | 0.0012 (7) | 0.0017 (6) |
C24 | 0.0241 (9) | 0.0178 (8) | 0.0170 (8) | 0.0010 (7) | −0.0013 (7) | 0.0011 (7) |
C25 | 0.0210 (9) | 0.0268 (10) | 0.0189 (8) | −0.0028 (8) | −0.0003 (7) | −0.0023 (7) |
O26 | 0.0252 (6) | 0.0270 (7) | 0.0173 (6) | −0.0038 (6) | 0.0023 (5) | 0.0005 (5) |
O22 | 0.0234 (6) | 0.0166 (6) | 0.0209 (6) | −0.0014 (5) | −0.0024 (5) | 0.0033 (5) |
C221 | 0.0253 (9) | 0.0228 (9) | 0.0208 (8) | 0.0011 (8) | −0.0007 (8) | −0.0025 (7) |
O221 | 0.0441 (8) | 0.0278 (7) | 0.0418 (8) | −0.0048 (7) | −0.0221 (7) | 0.0091 (7) |
C222 | 0.0340 (11) | 0.0244 (10) | 0.0261 (9) | −0.0052 (9) | 0.0000 (8) | −0.0035 (7) |
O23 | 0.0214 (6) | 0.0204 (6) | 0.0195 (6) | 0.0028 (5) | 0.0034 (5) | 0.0020 (5) |
C231 | 0.0226 (8) | 0.0180 (9) | 0.0205 (8) | −0.0053 (7) | 0.0013 (7) | −0.0016 (7) |
O231 | 0.0316 (7) | 0.0249 (7) | 0.0286 (7) | 0.0023 (6) | 0.0040 (6) | 0.0068 (6) |
C232 | 0.0303 (10) | 0.0243 (9) | 0.0321 (10) | −0.0019 (8) | 0.0127 (9) | 0.0021 (8) |
O24 | 0.0277 (6) | 0.0180 (6) | 0.0183 (6) | −0.0005 (6) | −0.0013 (5) | −0.0010 (5) |
C241 | 0.0232 (9) | 0.0206 (10) | 0.0287 (10) | 0.0002 (8) | 0.0015 (8) | −0.0039 (8) |
O241 | 0.0530 (9) | 0.0219 (7) | 0.0342 (7) | −0.0069 (7) | 0.0004 (7) | 0.0032 (6) |
C242 | 0.0326 (10) | 0.0256 (10) | 0.0271 (9) | −0.0004 (8) | −0.0017 (8) | −0.0065 (8) |
Geometric parameters (Å, º) top
N11A—C12A | 1.325 (2) | N16B—C21 | 1.46 (5) |
C12A—N13A | 1.352 (2) | N16B—H16B | 0.8800 |
N13A—C14A | 1.403 (3) | C21—O26 | 1.417 (2) |
C14A—C15A | 1.425 (3) | C21—C22 | 1.535 (2) |
C15A—C16A | 1.412 (2) | C21—H21 | 1.0000 |
C16A—N11A | 1.364 (2) | C22—O22 | 1.445 (2) |
C12A—S1A | 1.746 (2) | C22—C23 | 1.515 (2) |
N13A—H13A | 0.8800 | C22—H22 | 1.0000 |
C14A—O14A | 1.230 (2) | C23—O23 | 1.440 (2) |
C15A—C51A | 1.436 (3) | C23—C24 | 1.514 (2) |
C51A—O51A | 1.236 (3) | C23—H23 | 1.0000 |
C16A—N16A | 1.335 (3) | C24—O24 | 1.4452 (19) |
S1A—C17A | 1.810 (2) | C24—C25 | 1.517 (2) |
C17A—H17A | 0.9800 | C24—H24 | 1.0000 |
C17A—H17B | 0.9800 | C25—O26 | 1.4337 (19) |
C17A—H17C | 0.9800 | C25—H25A | 0.9900 |
C51A—H51A | 0.9500 | C25—H25B | 0.9900 |
N16A—C21 | 1.435 (5) | O22—C221 | 1.355 (2) |
N16A—H16A | 0.8800 | C221—O221 | 1.194 (2) |
N11B—C12B | 1.325 (5) | C221—C222 | 1.488 (3) |
N11B—C16B | 1.370 (5) | C222—H22A | 0.9800 |
C12B—N13B | 1.350 (5) | C222—H22B | 0.9800 |
C12B—S1B | 1.743 (4) | C222—H22C | 0.9800 |
N13B—C14B | 1.398 (5) | O23—C231 | 1.353 (2) |
N13B—H13B | 0.8800 | C231—O231 | 1.204 (2) |
C14B—O14B | 1.229 (5) | C231—C232 | 1.493 (3) |
C14B—C15B | 1.426 (5) | C232—H23A | 0.9800 |
C15B—C16B | 1.412 (4) | C232—H23B | 0.9800 |
C15B—C51B | 1.435 (5) | C232—H23C | 0.9800 |
C16B—N16B | 1.40 (2) | O24—C241 | 1.352 (2) |
S1B—C17B | 1.813 (5) | C241—O241 | 1.203 (2) |
C17B—H17D | 0.9800 | C241—C242 | 1.497 (2) |
C17B—H17E | 0.9800 | C242—H24A | 0.9800 |
C17B—H17F | 0.9800 | C242—H24B | 0.9800 |
C51B—O51B | 1.233 (6) | C242—H24C | 0.9800 |
C51B—H51B | 0.9500 | | |
| | | |
C12A—N11A—C16A | 116.38 (16) | N16A—C21—H21 | 110.9 |
N11A—C12A—N13A | 124.20 (17) | N16B—C21—H21 | 101.3 |
N11A—C12A—S1A | 113.14 (14) | C22—C21—H21 | 110.9 |
N13A—C12A—S1A | 122.66 (15) | O22—C22—C23 | 106.34 (13) |
C12A—N13A—C14A | 122.73 (16) | O22—C22—C21 | 108.35 (13) |
C12A—N13A—H13A | 118.6 | C23—C22—C21 | 110.23 (14) |
C14A—N13A—H13A | 118.6 | O22—C22—H22 | 110.6 |
O14A—C14A—N13A | 119.14 (17) | C23—C22—H22 | 110.6 |
O14A—C14A—C15A | 126.70 (19) | C21—C22—H22 | 110.6 |
N13A—C14A—C15A | 114.15 (16) | O23—C23—C24 | 108.50 (13) |
C16A—C15A—C14A | 119.36 (18) | O23—C23—C22 | 108.76 (14) |
C16A—C15A—C51A | 122.11 (17) | C24—C23—C22 | 109.02 (13) |
C14A—C15A—C51A | 118.53 (17) | O23—C23—H23 | 110.2 |
N16A—C16A—N11A | 118.3 (3) | C24—C23—H23 | 110.2 |
N16A—C16A—C15A | 118.6 (3) | C22—C23—H23 | 110.2 |
N11A—C16A—C15A | 123.08 (17) | O24—C24—C23 | 106.08 (13) |
C12A—S1A—C17A | 104.85 (9) | O24—C24—C25 | 112.16 (14) |
O51A—C51A—C15A | 126.29 (19) | C23—C24—C25 | 109.32 (14) |
O51A—C51A—H51A | 116.9 | O24—C24—H24 | 109.7 |
C15A—C51A—H51A | 116.9 | C23—C24—H24 | 109.7 |
C16A—N16A—C21 | 126.8 (4) | C25—C24—H24 | 109.7 |
C16A—N16A—H16A | 116.6 | O26—C25—C24 | 107.82 (14) |
C21—N16A—H16A | 116.6 | O26—C25—H25A | 110.1 |
C12B—N11B—C16B | 115.5 (4) | C24—C25—H25A | 110.1 |
N11B—C12B—N13B | 124.2 (4) | O26—C25—H25B | 110.1 |
N11B—C12B—S1B | 114.1 (4) | C24—C25—H25B | 110.1 |
N13B—C12B—S1B | 121.0 (4) | H25A—C25—H25B | 108.5 |
C12B—N13B—C14B | 122.9 (4) | C21—O26—C25 | 111.70 (13) |
C12B—N13B—H13B | 118.5 | C221—O22—C22 | 119.00 (13) |
C14B—N13B—H13B | 118.5 | O221—C221—O22 | 123.83 (17) |
O14B—C14B—N13B | 118.4 (5) | O221—C221—C222 | 126.01 (18) |
O14B—C14B—C15B | 127.4 (6) | O22—C221—C222 | 110.14 (15) |
N13B—C14B—C15B | 113.9 (3) | C221—C222—H22A | 109.5 |
C16B—C15B—C14B | 119.4 (3) | C221—C222—H22B | 109.5 |
C16B—C15B—C51B | 122.3 (4) | H22A—C222—H22B | 109.5 |
C14B—C15B—C51B | 118.3 (4) | C221—C222—H22C | 109.5 |
N11B—C16B—N16B | 116 (2) | H22A—C222—H22C | 109.5 |
N11B—C16B—C15B | 123.2 (4) | H22B—C222—H22C | 109.5 |
N16B—C16B—C15B | 116 (3) | C231—O23—C23 | 117.44 (13) |
C12B—S1B—C17B | 104.8 (3) | O231—C231—O23 | 123.71 (16) |
S1B—C17B—H17D | 109.5 | O231—C231—C232 | 125.55 (16) |
S1B—C17B—H17E | 109.5 | O23—C231—C232 | 110.74 (16) |
H17D—C17B—H17E | 109.5 | C231—C232—H23A | 109.5 |
S1B—C17B—H17F | 109.5 | C231—C232—H23B | 109.5 |
H17D—C17B—H17F | 109.5 | H23A—C232—H23B | 109.5 |
H17E—C17B—H17F | 109.5 | C231—C232—H23C | 109.5 |
O51B—C51B—C15B | 126.8 (7) | H23A—C232—H23C | 109.5 |
O51B—C51B—H51B | 116.6 | H23B—C232—H23C | 109.5 |
C15B—C51B—H51B | 116.6 | C241—O24—C24 | 116.20 (13) |
C16B—N16B—C21 | 140 (5) | O241—C241—O24 | 122.72 (17) |
C16B—N16B—H16B | 110.1 | O241—C241—C242 | 125.93 (18) |
C21—N16B—H16B | 110.1 | O24—C241—C242 | 111.35 (16) |
O26—C21—N16A | 103.8 (2) | C241—C242—H24A | 109.5 |
O26—C21—N16B | 106 (2) | C241—C242—H24B | 109.5 |
O26—C21—C22 | 109.98 (13) | H24A—C242—H24B | 109.5 |
N16A—C21—C22 | 110.0 (2) | C241—C242—H24C | 109.5 |
N16B—C21—C22 | 118 (2) | H24A—C242—H24C | 109.5 |
O26—C21—H21 | 110.9 | H24B—C242—H24C | 109.5 |
| | | |
C16A—N11A—C12A—N13A | −0.4 (4) | C14B—C15B—C51B—O51B | 158 (5) |
C16A—N11A—C12A—S1A | 179.0 (2) | N11B—C16B—N16B—C21 | 37 (8) |
N11A—C12A—N13A—C14A | 2.8 (3) | C15B—C16B—N16B—C21 | −165 (5) |
S1A—C12A—N13A—C14A | −176.44 (18) | C16A—N16A—C21—O26 | −137.7 (4) |
C12A—N13A—C14A—O14A | 176.5 (2) | C16A—N16A—C21—N16B | −36 (14) |
C12A—N13A—C14A—C15A | −4.0 (4) | C16A—N16A—C21—C22 | 104.6 (4) |
O14A—C14A—C15A—C16A | −177.6 (3) | C16B—N16B—C21—O26 | −164 (5) |
N13A—C14A—C15A—C16A | 3.0 (5) | C16B—N16B—C21—N16A | 115 (17) |
O14A—C14A—C15A—C51A | 2.1 (5) | C16B—N16B—C21—C22 | 73 (6) |
N13A—C14A—C15A—C51A | −177.3 (3) | O26—C21—C22—O22 | 171.45 (13) |
C12A—N11A—C16A—N16A | −178.9 (3) | N16A—C21—C22—O22 | −74.7 (2) |
C12A—N11A—C16A—C15A | −0.6 (5) | N16B—C21—C22—O22 | −68 (2) |
C14A—C15A—C16A—N16A | 177.5 (4) | O26—C21—C22—C23 | 55.47 (17) |
C51A—C15A—C16A—N16A | −2.2 (6) | N16A—C21—C22—C23 | 169.3 (2) |
C14A—C15A—C16A—N11A | −0.9 (6) | N16B—C21—C22—C23 | 176 (2) |
C51A—C15A—C16A—N11A | 179.5 (3) | O22—C22—C23—O23 | 71.26 (16) |
N11A—C12A—S1A—C17A | −176.69 (18) | C21—C22—C23—O23 | −171.51 (13) |
N13A—C12A—S1A—C17A | 2.7 (2) | O22—C22—C23—C24 | −170.61 (12) |
C16A—C15A—C51A—O51A | 3.9 (7) | C21—C22—C23—C24 | −53.37 (18) |
C14A—C15A—C51A—O51A | −175.7 (5) | O23—C23—C24—O24 | −63.37 (16) |
N11A—C16A—N16A—C21 | −4.2 (6) | C22—C23—C24—O24 | 178.33 (13) |
C15A—C16A—N16A—C21 | 177.4 (4) | O23—C23—C24—C25 | 175.49 (13) |
C16B—N11B—C12B—N13B | −10 (4) | C22—C23—C24—C25 | 57.20 (18) |
C16B—N11B—C12B—S1B | 179 (3) | O24—C24—C25—O26 | −179.47 (13) |
N11B—C12B—N13B—C14B | 12 (4) | C23—C24—C25—O26 | −62.10 (18) |
S1B—C12B—N13B—C14B | −177.9 (18) | N16A—C21—O26—C25 | −179.94 (19) |
C12B—N13B—C14B—O14B | 167 (2) | N16B—C21—O26—C25 | 169.9 (19) |
C12B—N13B—C14B—C15B | −7 (4) | C22—C21—O26—C25 | −62.23 (17) |
O14B—C14B—C15B—C16B | −171 (4) | C24—C25—O26—C21 | 65.48 (18) |
N13B—C14B—C15B—C16B | 2 (6) | C23—C22—O22—C221 | −137.55 (15) |
O14B—C14B—C15B—C51B | 10 (6) | C21—C22—O22—C221 | 103.97 (16) |
N13B—C14B—C15B—C51B | −177 (4) | C22—O22—C221—O221 | −0.6 (3) |
C12B—N11B—C16B—N16B | 162 (4) | C22—O22—C221—C222 | −179.02 (13) |
C12B—N11B—C16B—C15B | 6 (6) | C24—C23—O23—C231 | 121.87 (15) |
C14B—C15B—C16B—N11B | −2 (7) | C22—C23—O23—C231 | −119.67 (15) |
C51B—C15B—C16B—N11B | 177 (4) | C23—O23—C231—O231 | 7.1 (2) |
C14B—C15B—C16B—N16B | −158 (4) | C23—O23—C231—C232 | −172.85 (14) |
C51B—C15B—C16B—N16B | 20 (7) | C23—C24—O24—C241 | 151.74 (14) |
N11B—C12B—S1B—C17B | −11 (2) | C25—C24—O24—C241 | −88.97 (19) |
N13B—C12B—S1B—C17B | 177.9 (19) | C24—O24—C241—O241 | 9.5 (3) |
C16B—C15B—C51B—O51B | −20 (8) | C24—O24—C241—C242 | −170.37 (14) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N13A—H13A···O221i | 0.88 | 2.11 | 2.942 (2) | 157 |
N13B—H13B···O221i | 0.88 | 1.96 | 2.780 (9) | 155 |
N16A—H16A···O51A | 0.88 | 1.92 | 2.645 (6) | 139 |
N16B—H16B···O51B | 0.88 | 2.01 | 2.68 (6) | 132 |
C22—H22···O14Aii | 1.00 | 2.31 | 3.304 (2) | 171 |
C22—H22···O14Bii | 1.00 | 2.52 | 3.468 (15) | 159 |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2. |
Experimental details
| (I) | (II) |
Crystal data |
Chemical formula | C18H23N3O10·0.065H2O | C17H21N3O9S |
Mr | 442.57 | 443.44 |
Crystal system, space group | Orthorhombic, P212121 | Orthorhombic, P212121 |
Temperature (K) | 120 | 120 |
a, b, c (Å) | 14.3816 (2), 14.7626 (2), 20.1025 (3) | 6.9294 (1), 10.7415 (2), 26.4825 (5) |
V (Å3) | 4267.96 (10) | 1971.15 (6) |
Z | 8 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.11 | 0.22 |
Crystal size (mm) | 0.22 × 0.20 × 0.18 | 0.44 × 0.35 × 0.30 |
|
Data collection |
Diffractometer | Bruker–Nonius KappaCCD diffractometer | Bruker–Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2003) | Multi-scan (SADABS; Sheldrick, 2003) |
Tmin, Tmax | 0.975, 0.980 | 0.885, 0.936 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 70888, 5407, 4925 | 12812, 4482, 4065 |
Rint | 0.041 | 0.031 |
(sin θ/λ)max (Å−1) | 0.650 | 0.649 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.088, 1.08 | 0.038, 0.096, 1.14 |
No. of reflections | 5407 | 4482 |
No. of parameters | 581 | 327 |
No. of restraints | 3 | 40 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.20 | 0.42, −0.45 |
Absolute structure | ? | Flack (1983) |
Absolute structure parameter | ? | −0.02 (7) |
Selected geometric parameters (Å, º) for (I) topN11—C12 | 1.304 (2) | N31—C32 | 1.303 (2) |
C12—N13 | 1.351 (3) | C32—N33 | 1.352 (2) |
N13—C14 | 1.413 (2) | N33—C34 | 1.417 (3) |
C14—C15 | 1.439 (3) | C34—C35 | 1.437 (3) |
C15—C16 | 1.411 (3) | C35—C36 | 1.405 (3) |
C16—N11 | 1.362 (2) | C36—N31 | 1.364 (2) |
C12—O12 | 1.328 (2) | C32—O32 | 1.325 (2) |
C14—O14 | 1.223 (2) | C34—O34 | 1.226 (2) |
C15—C51 | 1.432 (3) | C35—C53 | 1.432 (3) |
C51—O51 | 1.241 (2) | C53—O53 | 1.232 (3) |
C16—N16 | 1.345 (2) | C36—N36 | 1.350 (2) |
| | | |
N11—C12—O12—C121 | 5.9 (3) | N31—C32—O32—C321 | 2.6 (3) |
C16—C15—C51—O51 | −0.5 (3) | C36—C35—C53—O53 | 1.4 (3) |
Hydrogen-bond geometry (Å, º) for (I) top
D—H···A | D—H | H···A | D···A | D—H···A |
N16—H16···O51 | 0.88 | 2.03 | 2.707 (2) | 133 |
N36—H36···O53 | 0.88 | 2.06 | 2.725 (2) | 132 |
C24—H24···O14i | 1.00 | 2.34 | 3.237 (3) | 148 |
C44—H44···O231 | 1.00 | 2.28 | 3.213 (3) | 155 |
C45—H45B···O34ii | 0.99 | 2.38 | 3.245 (3) | 145 |
C51—H51···O241iii | 0.95 | 2.54 | 3.442 (3) | 159 |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x+1/2, −y+1/2, −z+1; (iii) −x+1, y−1/2, −z+3/2. |
Selected geometric parameters (Å, º) for (II) topN11A—C12A | 1.325 (2) | C12A—S1A | 1.746 (2) |
C12A—N13A | 1.352 (2) | C14A—O14A | 1.230 (2) |
N13A—C14A | 1.403 (3) | C15A—C51A | 1.436 (3) |
C14A—C15A | 1.425 (3) | C51A—O51A | 1.236 (3) |
C15A—C16A | 1.412 (2) | C16A—N16A | 1.335 (3) |
C16A—N11A | 1.364 (2) | | |
| | | |
N11A—C12A—S1A—C17A | −176.69 (18) | N11B—C12B—S1B—C17B | −11 (2) |
C16A—C15A—C51A—O51A | 3.9 (7) | C16B—C15B—C51B—O51B | −20 (8) |
Hydrogen-bond geometry (Å, º) for (II) top
D—H···A | D—H | H···A | D···A | D—H···A |
N13A—H13A···O221i | 0.88 | 2.11 | 2.942 (2) | 157 |
N13B—H13B···O221i | 0.88 | 1.96 | 2.780 (9) | 155 |
N16A—H16A···O51A | 0.88 | 1.92 | 2.645 (6) | 139 |
N16B—H16B···O51B | 0.88 | 2.01 | 2.68 (6) | 132 |
C22—H22···O14Aii | 1.00 | 2.31 | 3.304 (2) | 171 |
C22—H22···O14Bii | 1.00 | 2.52 | 3.468 (15) | 159 |
Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, y−1/2, −z+3/2. |
5-Substituted aminopyrimidine derivatives are useful intermediates for the preparation of fused pyrimidine systems, and we have previously reported the preparation of 5-formyl-6-glycosylaminopyrimidines under Vilsmeier–Haack conditions (Negrillo et al., 1988). We report here the structures of two representative examples of 6-oxo-4-(2,3,4-tri-O-acetyl-β-D-xylopyranosylamino)-1,6-dihydropyrimidine-5-carbaldehydes, viz. (I) and (II) (Figs. 1 and 2), of which (I) is a partial hydrate containing 0.065 (3) molecules of water per molecule of the organic component. Compounds (I) and (II) both crystallize in the space group P212121, but with Z' values of 2 and 1, respectively, and so that their unit-cell dimensions show no obvious simple relationship to one another. In compound (II), the pyrimidine component is disordered, and this disorder was modelled using two sets of sites with refined occupancies 0.899 (2) and 0.101 (2); an unexpected feature of the disorder is that the methylsulfanyl substituent adopts different conformations in the two disorder components.
The xylopyranose rings in both compounds adopt almost perfect chair conformations, with all of the non-H substituents occupying equatorial sites, giving the absolute configuration in (II) as (x1R,x2R,x3S,x4R), where x = 2 or 4, with the absolute configuration in (I) set to be identical. The pyrimidine rings are all planar despite the heavy degree of substitution. The formyl groups are all oriented so that intramolecular N—H···O hydrogen bonds (Tables 2 and 4) can form; these interactions may play a role in controlling the orientation of the formyl group (Cobo et al., 2008). The methoxy C atoms in (I) are oriented on the same side of the pyrimidine ring as the formyl O atom, whereas in (II) the methylsulfanyl C atoms is oriented to the opposite side in the major component and to the same side in the minor component (Tables 1 and 3, and Figs. 1 and 2); no obvious simple explanation for these differences presents itself. The bond lengths within the pyrimidine systems (Tables 1 and 3) provide some evidence for the polarization of the electronic structures. In particular, the formyl C—O distances are all long for their type (Allen et al., 1987), as are the exocyclic C—N bonds, while the C—C bonds linking the formyl unit to the ring are all long, suggesting the importance of the polarized forms (Ia) and (IIa) (see scheme). The intramolecular N—H···O hydrogen bonds can thus be regarded as charge-assisted hydrogen bonds (Gilli et al., 1994).
In compound (I), the organic components are linked by four C—H···O hydrogen bonds (Table 2) to form a three-dimensional framework structure of some complexity; however, the formation of this framework can readily be analysed in terms of three distinct one-dimensional substructures. One of the hydrogen bonds links the two molecules within the selected asymmetric unit, while the other three give rise, in various combinations, to the three substructures, The simplest of the substructures, along [100], depends on just one hydrogen bond and involves only the type 2 molecules, containing atom N31 (Fig. 1). Atom C45 at (x, y, z) acts as hydrogen-bond donor to atom O34 at (1/2+x, 1/2-y, 1-z), so linking type 2 molecules related by the 21 screw axis along (x, 1/4, 1/2) into a C(9) (Bernstein et al., 1995) chain running parallel to the [100] direction (Fig. 3).
In a somewhat similar manner, the substructure along [010] involves only the type 1 molecules, containing atom N11 (Fig. 1), but now two hydrogen bonds are involved. Atoms C24 and C51 at (x, y, z) act as hydrogen-bond donors, respectively, to atom O14 at (1-x, 1/2+y, 1.5-z) and O241 at (1-x, -1/2+y, 1.5-z), so linking type 1 molecules related by the 21 screw axis along (1/2, y, 3/4) into a C(10)C(12)[R22(10)] chain of rings running parallel to the [010] direction (Fig. 4). The final substructure, along [001], involves both types of molecule and all four of the C—H···O hydrogen bonds (Fig. 5). The combination of the chains parallel to [100], [010] and [001] suffices to link all of the molecules of (I) into a continuous framework structure.
The hydrogen-bonded structure of compound (II), is much simpler than that of (I) and involves only two hydrogen bonds, one each of the N—H···O and C—H···O types (Table 4). The same pattern of hydrogen bonds is evident for both components of the disordered pyrimidine unit, so that the disorder has no effect on the supramolecular aggregation. Atoms N13n and C22n (n = A or B) at (x, y, z) act as hydrogen-bond donors, respectively, to atom O221 at (1-x, 1/2+y, 1.5-z) and O14n at (1-x, 1/2+y, 1.5-z), thereby linking molecules related by the 21 screw axis along (1/2, y, 3/4) into a C(8)C(11)[R22(9)] chain of rings running parallel to the [010] direction (Fig. 6).
There are thus both similarities and differences between the chains of rings along [010] formed in compound (II) and by the type 1 molecules in compound (I). Each chain is formed from molecules related by the 21 screw axis along (1/2, y, 3/4) and each is built from two hydrogen bonds acting in the two opposite directions along [010]. However, in (I), these hydrogen bonds are both of the C—H···O type, while in (II) there is one each of the N—H···O and C—H···O types, although the same two acceptor O atoms are involved in both structures. The use of different donor atoms in the two structures necessarily leads to different hydrogen-bond motifs and to different graph-set descriptors, C(10)C(12)[R22(10)] in (I) and C(8)C(11)[R22(9)] in (II).