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The two independent mol­ecules of C8H4N2O4F6S are linked by a pair of Namido...Npyridyl interactions [2.858 (2) and 2.880 (2) Å], giving rise to a hydrogen-bonded dimer. The conformation of the tri­fluoro­methane­sulfonate moiety is different in the two mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804001679/ci6333sup1.cif
Contains datablocks I, sad

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804001679/ci6333Isup2.hkl
Contains datablock I

CCDC reference: 234922

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.032
  • wR factor = 0.087
  • Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT431_ALERT_2_C Short Inter HL..A Contact F1A .. O1 = 2.94 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact F4A .. N1 = 3.00 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-II (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Trifluoromethanesulfonic acid 2-(2,2,2-trifluoroacetylamino)pyridin-3-yl ester top
Crystal data top
C8H4F6N2O4SZ = 4
Mr = 338.19F(000) = 672
Triclinic, P1Dx = 1.911 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.8702 (5) ÅCell parameters from 6114 reflections
b = 10.0063 (5) Åθ = 2.4–28.3°
c = 12.6434 (6) ŵ = 0.38 mm1
α = 101.436 (1)°T = 100 K
β = 103.466 (1)°Block, colorless
γ = 95.981 (1)°0.40 × 0.35 × 0.30 mm
V = 1175.4 (1) Å3
Data collection top
Bruker SMART area-detector
diffractometer
4725 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.018
Graphite monochromatorθmax = 27.5°, θmin = 1.7°
φ and ω scansh = 1212
13584 measured reflectionsk = 1212
5315 independent reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.052P)2 + 0.4147P]
where P = (Fo2 + 2Fc2)/3
5315 reflections(Δ/σ)max = 0.001
387 parametersΔρmax = 0.51 e Å3
2 restraintsΔρmin = 0.33 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.17960 (4)0.31719 (4)0.47544 (3)0.0180 (1)
F10.4371 (1)0.3938 (1)0.6015 (1)0.0293 (2)
F20.3656 (1)0.1741 (1)0.5535 (1)0.0332 (3)
F30.2924 (1)0.3017 (1)0.6805 (1)0.0283 (2)
F40.2010 (1)0.6161 (1)0.9631 (1)0.0287 (2)
F50.3765 (1)0.5314 (1)0.9178 (1)0.0297 (2)
F60.1701 (1)0.4100 (1)0.8639 (1)0.0313 (2)
O10.0671 (1)0.2142 (1)0.4680 (1)0.0268 (3)
O20.2348 (1)0.3356 (1)0.3850 (1)0.0257 (3)
O30.1409 (1)0.4566 (1)0.5364 (1)0.0164 (2)
O40.0796 (1)0.5904 (1)0.7312 (1)0.0209 (2)
N10.3692 (1)0.7888 (1)0.6362 (1)0.0179 (3)
N20.3135 (1)0.6265 (1)0.7350 (1)0.0154 (3)
C10.3285 (2)0.2956 (2)0.5855 (1)0.0223 (3)
C20.2958 (2)0.6679 (2)0.6330 (1)0.0154 (3)
C30.2113 (2)0.5846 (2)0.5331 (1)0.0157 (3)
C40.1948 (2)0.6283 (2)0.4348 (1)0.0199 (3)
C50.2705 (2)0.7544 (2)0.4390 (1)0.0227 (3)
C60.3571 (2)0.8299 (2)0.5403 (1)0.0219 (3)
C70.2023 (2)0.5894 (2)0.7736 (1)0.0164 (3)
C80.2399 (2)0.5366 (2)0.8816 (1)0.0188 (3)
S1a0.88367 (4)1.05918 (4)0.79092 (3)0.0152 (1)
F1a1.0824 (1)0.9122 (1)0.7665 (1)0.0248 (2)
F2a1.1543 (1)1.1195 (1)0.8661 (1)0.0252 (2)
F3a1.0767 (1)1.0839 (1)0.6869 (1)0.0285 (2)
F4a0.3862 (1)1.0690 (1)0.7824 (1)0.0233 (2)
F5a0.5703 (1)1.2231 (1)0.8227 (1)0.0287 (2)
F6a0.4527 (1)1.2092 (1)0.9445 (1)0.0256 (2)
O1a0.8833 (1)1.2017 (1)0.8293 (1)0.0219 (2)
O2a0.7862 (1)0.9785 (1)0.6928 (1)0.0197 (2)
O3a0.8843 (1)0.9924 (1)0.8946 (1)0.0157 (2)
O4a0.6721 (1)1.0735 (1)1.0041 (1)0.0214 (2)
N1a0.6134 (1)0.6904 (1)0.8337 (1)0.0166 (3)
N2a0.5857 (1)0.9189 (1)0.8343 (1)0.0157 (3)
C1a1.0623 (2)1.0415 (2)0.7767 (1)0.0190 (3)
C2a0.6755 (2)0.8199 (2)0.8513 (1)0.0145 (3)
C3a0.8214 (2)0.8540 (2)0.8784 (1)0.0154 (3)
C4a0.9064 (2)0.7552 (2)0.8942 (1)0.0176 (3)
C5a0.8409 (2)0.6211 (2)0.8783 (1)0.0189 (3)
C6a0.6950 (2)0.5928 (2)0.8466 (1)0.0189 (3)
C7a0.5945 (2)1.0372 (2)0.9106 (1)0.0164 (3)
C8a0.4980 (2)1.1355 (2)0.8650 (1)0.0185 (3)
H2n0.398 (1)0.637 (2)0.774 (2)0.032 (6)*
H40.13370.57400.36680.024*
H50.26320.78870.37330.027*
H60.41080.91520.54190.026*
H2na0.518 (2)0.893 (2)0.776 (1)0.026 (5)*
H4a1.00630.77830.91530.021*
H5a0.89520.54950.88880.023*
H6a0.65070.50000.83350.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0211 (2)0.0142 (2)0.0168 (2)0.0013 (1)0.0038 (1)0.0010 (1)
F10.0193 (5)0.0275 (5)0.0378 (6)0.0026 (4)0.0031 (4)0.0058 (4)
F20.0402 (6)0.0222 (5)0.0373 (6)0.0166 (5)0.0075 (5)0.0043 (4)
F30.0388 (6)0.0272 (5)0.0213 (5)0.0100 (4)0.0071 (4)0.0097 (4)
F40.0409 (6)0.0296 (5)0.0177 (5)0.0088 (5)0.0114 (4)0.0045 (4)
F50.0225 (5)0.0425 (6)0.0287 (5)0.0067 (4)0.0045 (4)0.0208 (5)
F60.0426 (6)0.0201 (5)0.0284 (5)0.0084 (4)0.0079 (5)0.0078 (4)
O10.0281 (6)0.0178 (6)0.0291 (6)0.0032 (5)0.0052 (5)0.0004 (5)
O20.0360 (7)0.0219 (6)0.0207 (6)0.0067 (5)0.0109 (5)0.0033 (5)
O30.0154 (5)0.0140 (5)0.0178 (5)0.0001 (4)0.0030 (4)0.0018 (4)
O40.0160 (5)0.0256 (6)0.0204 (6)0.0032 (4)0.0048 (4)0.0037 (4)
N10.0189 (6)0.0144 (6)0.0197 (6)0.0017 (5)0.0038 (5)0.0044 (5)
N20.0139 (6)0.0160 (6)0.0148 (6)0.0000 (5)0.0014 (5)0.0038 (5)
C10.0247 (8)0.0189 (8)0.0235 (8)0.0075 (6)0.0045 (6)0.0049 (6)
C20.0142 (7)0.0153 (7)0.0173 (7)0.0040 (5)0.0038 (5)0.0046 (5)
C30.0153 (7)0.0128 (7)0.0195 (7)0.0026 (5)0.0046 (6)0.0045 (6)
C40.0187 (7)0.0225 (8)0.0170 (7)0.0044 (6)0.0007 (6)0.0049 (6)
C50.0262 (8)0.0234 (8)0.0211 (8)0.0060 (7)0.0051 (6)0.0117 (6)
C60.0237 (8)0.0177 (7)0.0261 (8)0.0027 (6)0.0065 (6)0.0095 (6)
C70.0183 (7)0.0128 (7)0.0163 (7)0.0004 (6)0.0043 (6)0.0008 (5)
C80.0193 (7)0.0187 (7)0.0184 (7)0.0000 (6)0.0053 (6)0.0049 (6)
S1a0.0138 (2)0.0148 (2)0.0166 (2)0.0006 (1)0.0026 (1)0.0052 (1)
F1a0.0233 (5)0.0227 (5)0.0298 (5)0.0069 (4)0.0094 (4)0.0048 (4)
F2a0.0144 (4)0.0288 (5)0.0267 (5)0.0021 (4)0.0017 (4)0.0004 (4)
F3a0.0264 (5)0.0375 (6)0.0266 (5)0.0017 (4)0.0120 (4)0.0143 (4)
F4a0.0189 (5)0.0218 (5)0.0247 (5)0.0060 (4)0.0011 (4)0.0016 (4)
F5a0.0248 (5)0.0262 (5)0.0419 (6)0.0055 (4)0.0110 (4)0.0202 (5)
F6a0.0271 (5)0.0218 (5)0.0270 (5)0.0093 (4)0.0078 (4)0.0006 (4)
O1a0.0229 (6)0.0156 (5)0.0268 (6)0.0024 (4)0.0057 (5)0.0056 (4)
O2a0.0190 (5)0.0215 (6)0.0170 (5)0.0001 (4)0.0009 (4)0.0066 (4)
O3a0.0148 (5)0.0156 (5)0.0148 (5)0.0006 (4)0.0014 (4)0.0040 (4)
O4a0.0232 (6)0.0210 (6)0.0180 (5)0.0039 (5)0.0027 (4)0.0026 (4)
N1a0.0178 (6)0.0160 (6)0.0163 (6)0.0012 (5)0.0051 (5)0.0042 (5)
N2a0.0136 (6)0.0154 (6)0.0164 (6)0.0011 (5)0.0017 (5)0.0032 (5)
C1a0.0166 (7)0.0205 (8)0.0199 (8)0.0010 (6)0.0057 (6)0.0046 (6)
C2a0.0167 (7)0.0150 (7)0.0124 (7)0.0028 (5)0.0042 (5)0.0041 (5)
C3a0.0185 (7)0.0151 (7)0.0120 (7)0.0001 (6)0.0037 (5)0.0035 (5)
C4a0.0164 (7)0.0229 (8)0.0149 (7)0.0046 (6)0.0047 (5)0.0058 (6)
C5a0.0223 (8)0.0189 (7)0.0190 (7)0.0081 (6)0.0072 (6)0.0077 (6)
C6a0.0244 (8)0.0158 (7)0.0176 (7)0.0018 (6)0.0071 (6)0.0050 (6)
C7a0.0157 (7)0.0162 (7)0.0187 (7)0.0017 (6)0.0065 (6)0.0054 (6)
C8a0.0170 (7)0.0164 (7)0.0211 (8)0.0020 (6)0.0044 (6)0.0032 (6)
Geometric parameters (Å, º) top
S1—O11.406 (1)F1a—C1a1.315 (2)
S1—O21.411 (1)F2a—C1a1.318 (2)
S1—O31.584 (1)F3a—C1a1.320 (2)
S1—C11.837 (2)F4a—C8a1.336 (2)
F1—C11.325 (2)F5a—C8a1.340 (2)
F2—C11.321 (2)F6a—C8a1.319 (2)
F3—C11.322 (2)O3a—C3a1.413 (2)
F4—C81.329 (2)O4a—C7a1.211 (2)
F5—C81.330 (2)N1a—C2a1.327 (2)
F6—C81.328 (2)N1a—C6a1.340 (2)
O3—C31.405 (2)N2a—C7a1.352 (2)
O4—C71.207 (2)N2a—C2a1.411 (2)
N1—C21.332 (2)C2a—C3a1.389 (2)
N1—C61.340 (2)C3a—C4a1.376 (2)
N2—C71.348 (2)C4a—C5a1.382 (2)
N2—C21.410 (2)C5a—C6a1.384 (2)
C2—C31.390 (2)C7a—C8a1.540 (2)
C3—C41.378 (2)N2—H2n0.85 (1)
C4—C51.383 (2)C4—H40.95
C5—C61.383 (2)C5—H50.95
C7—C81.540 (2)C6—H60.95
S1a—O1a1.413 (1)N2a—H2na0.85 (1)
S1a—O2a1.415 (1)C4a—H4a0.95
S1a—O3a1.584 (1)C5a—H5a0.95
S1a—C1a1.836 (2)C6a—H6a0.95
O1—S1—O2124.4 (1)C7a—N2a—C2a123.5 (1)
O1—S1—O3105.4 (1)F1a—C1a—F2a109.7 (1)
O2—S1—O3111.4 (1)F1a—C1a—F3a109.8 (1)
O1—S1—C1106.5 (1)F2a—C1a—F3a109.9 (1)
O2—S1—C1106.4 (1)F1a—C1a—S1a110.7 (1)
O3—S1—C1100.0 (1)F2a—C1a—S1a108.7 (1)
C3—O3—S1120.4 (1)F3a—C1a—S1a108.1 (1)
C2—N1—C6118.0 (1)N1a—C2a—C3a121.3 (1)
C7—N2—C2121.6 (1)N1a—C2a—N2a116.6 (1)
F2—C1—F3109.4 (1)C3a—C2a—N2a122.0 (1)
F2—C1—F1109.1 (1)C4a—C3a—C2a120.8 (1)
F3—C1—F1109.0 (1)C4a—C3a—O3a119.3 (1)
F2—C1—S1108.5 (1)C2a—C3a—O3a119.9 (1)
F3—C1—S1110.7 (1)C3a—C4a—C5a117.5 (1)
F1—C1—S1110.2 (1)C4a—C5a—C6a118.9 (1)
N1—C2—C3121.5 (1)N1a—C6a—C5a123.0 (1)
N1—C2—N2116.5 (1)O4a—C7a—N2a127.5 (1)
C3—C2—N2122.0 (1)O4a—C7a—C8a119.6 (1)
C4—C3—C2120.7 (1)N2a—C7a—C8a112.8 (1)
C4—C3—O3121.4 (1)F6a—C8a—F4a108.5 (1)
C2—C3—O3117.8 (1)F6a—C8a—F5a107.9 (1)
C5—C4—C3117.4 (1)F4a—C8a—F5a106.7 (1)
C4—C5—C6119.0 (1)F6a—C8a—C7a111.4 (1)
N1—C6—C5123.3 (2)F4a—C8a—C7a112.7 (1)
O4—C7—N2127.0 (1)F5a—C8a—C7a109.5 (1)
O4—C7—C8118.3 (1)C7—N2—H2n123 (2)
N2—C7—C8114.7 (1)C2—N2—H2n115 (2)
F6—C8—F4107.4 (1)C5—C4—H4121.3
F6—C8—F5107.6 (1)C3—C4—H4121.3
F4—C8—F5108.0 (1)C4—C5—H5120.5
F6—C8—C7109.4 (1)C6—C5—H5120.5
F4—C8—C7110.6 (1)N1—C6—H6118.4
F5—C8—C7113.7 (1)C5—C6—H6118.4
O1a—S1a—O2a122.4 (1)C7a—N2a—H2na122 (1)
O1a—S1a—O3a106.2 (1)C2a—N2a—H2na114 (1)
O2a—S1a—O3a111.4 (1)C3a—C4a—H4a121.2
O1a—S1a—C1a106.6 (1)C5a—C4a—H4a121.2
O2a—S1a—C1a108.0 (1)C4a—C5a—H5a120.6
O3a—S1a—C1a99.9 (1)C6a—C5a—H5a120.6
C3a—O3a—S1a120.5 (1)N1a—C6a—H6a118.5
C2a—N1a—C6a118.4 (1)C5a—C6a—H6a118.5
O1—S1—O3—C3164.0 (1)O1a—S1a—O3a—C3a150.5 (1)
O2—S1—O3—C326.4 (1)O2a—S1a—O3a—C3a15.0 (1)
C1—S1—O3—C385.7 (1)C1a—S1a—O3a—C3a98.9 (1)
O1—S1—C1—F263.7 (1)O1a—S1a—C1a—F1a165.5 (1)
O2—S1—C1—F270.9 (1)O2a—S1a—C1a—F1a61.3 (1)
O3—S1—C1—F2173.1 (1)O3a—S1a—C1a—F1a55.2 (1)
O1—S1—C1—F356.3 (1)O1a—S1a—C1a—F2a44.9 (1)
O2—S1—C1—F3169.1 (1)O2a—S1a—C1a—F2a178.1 (1)
O3—S1—C1—F353.1 (1)O3a—S1a—C1a—F2a65.4 (1)
O1—S1—C1—F1176.9 (1)O1a—S1a—C1a—F3a74.3 (1)
O2—S1—C1—F148.6 (1)O2a—S1a—C1a—F3a59.0 (1)
O3—S1—C1—F167.5 (1)O3a—S1a—C1a—F3a175.5 (1)
C6—N1—C2—C31.4 (2)C6a—N1a—C2a—C3a2.4 (2)
C6—N1—C2—N2178.6 (1)C6a—N1a—C2a—N2a178.7 (1)
C7—N2—C2—N1127.0 (2)C7a—N2a—C2a—N1a128.3 (2)
C7—N2—C2—C355.8 (2)C7a—N2a—C2a—C3a55.5 (2)
N1—C2—C3—C43.6 (2)N1a—C2a—C3a—C4a3.9 (2)
N2—C2—C3—C4179.3 (1)N2a—C2a—C3a—C4a179.9 (1)
N1—C2—C3—O3178.0 (1)N1a—C2a—C3a—O3a178.8 (1)
N2—C2—C3—O31.0 (2)N2a—C2a—C3a—O3a2.8 (2)
S1—O3—C3—C467.2 (2)S1a—O3a—C3a—C4a106.8 (1)
S1—O3—C3—C2114.5 (1)S1a—O3a—C3a—C2a75.8 (2)
C2—C3—C4—C53.1 (2)C2a—C3a—C4a—C5a2.2 (2)
O3—C3—C4—C5178.7 (1)O3a—C3a—C4a—C5a179.6 (1)
C3—C4—C5—C60.5 (2)C3a—C4a—C5a—C6a0.5 (2)
C2—N1—C6—C51.3 (2)C2a—N1a—C6a—C5a0.4 (2)
C4—C5—C6—N11.7 (3)C4a—C5a—C6a—N1a1.9 (2)
C2—N2—C7—O42.5 (2)C2a—N2a—C7a—O4a3.9 (2)
C2—N2—C7—C8175.6 (1)C2a—N2a—C7a—C8a172.2 (1)
O4—C7—C8—F655.7 (2)O4a—C7a—C8a—F6a35.1 (2)
N2—C7—C8—F6122.5 (1)N2a—C7a—C8a—F6a148.5 (1)
O4—C7—C8—F462.4 (2)O4a—C7a—C8a—F4a157.3 (1)
N2—C7—C8—F4119.4 (1)N2a—C7a—C8a—F4a26.3 (2)
O4—C7—C8—F5176.0 (1)O4a—C7a—C8a—F5a84.1 (2)
N2—C7—C8—F52.2 (2)N2a—C7a—C8a—F5a92.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2n···N1a0.85 (1)2.06 (1)2.880 (2)164 (2)
N2a—H2na···N10.85 (1)2.02 (1)2.858 (2)167 (2)
 

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