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In the crystal structure of the title compound, C6H11N3O22+·C4F4O42-, the anions and cations are linked to each other through hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804004180/na6294sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804004180/na6294Isup2.hkl
Contains datablock I

CCDC reference: 238696

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.022
  • wR factor = 0.056
  • Data-to-parameter ratio = 6.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT432_ALERT_2_B Short Inter X...Y Contact F3 .. C3 .. 2.86 Ang.
Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.34 PLAT431_ALERT_2_C Short Inter HL..A Contact F3 .. O6 .. 2.98 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.99 From the CIF: _reflns_number_total 1413 Count of symmetry unique reflns 1412 Completeness (_total/calc) 100.07% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1 Fraction of Friedel pairs measured 0.001 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 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 1 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: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Farrugia, 1997); software used to prepare material for publication: PARST (Nardelli, 1995) and WinGX (Farrugia, 1999).

L-histidinium tetrafluorosuccinate top
Crystal data top
C6H11N3O22+·C4F4O42F(000) = 704
Mr = 345.22Dx = 1.779 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2yCell parameters from 21085 reflections
a = 21.8863 (16) Åθ = 1.8–29.9°
b = 5.1411 (4) ŵ = 0.18 mm1
c = 15.5619 (12) ÅT = 293 K
β = 132.601 (5)°Block, colourless
V = 1288.9 (2) Å30.56 × 0.48 × 0.36 mm
Z = 4
Data collection top
Stoe IPDS 2
diffractometer
1413 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus1374 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.032
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 1.8°
ω scansh = 2626
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 66
Tmin = 0.906, Tmax = 0.938l = 1918
12924 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.022H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.056 w = 1/[σ2(Fo2) + (0.0296P)2 + 0.5241P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
1413 reflectionsΔρmax = 0.22 e Å3
223 parametersΔρmin = 0.19 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0264 (18)
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.24064 (9)0.4506 (3)0.07144 (13)0.0338 (4)
O20.36130 (8)0.6629 (3)0.17469 (13)0.0353 (4)
N10.38737 (10)0.5093 (4)0.48735 (13)0.0319 (5)
N20.30145 (9)0.8253 (4)0.40107 (13)0.0266 (4)
N30.16775 (9)0.8316 (4)0.09251 (13)0.0258 (4)
C10.33574 (10)0.8073 (4)0.35236 (14)0.0229 (5)
C20.38977 (11)0.6072 (5)0.40733 (15)0.0295 (5)
C30.33386 (11)0.6453 (5)0.48182 (15)0.0305 (5)
C40.31258 (11)0.9919 (4)0.26055 (15)0.0236 (5)
C50.25209 (10)0.8835 (4)0.13627 (14)0.0212 (5)
C60.28341 (11)0.6383 (4)0.12341 (14)0.0229 (5)
F10.64530 (7)0.1552 (3)0.36415 (10)0.0360 (3)
F20.58220 (8)0.2542 (3)0.18492 (12)0.0450 (5)
F30.53414 (7)0.2686 (2)0.27280 (11)0.0363 (4)
F40.46968 (7)0.1148 (3)0.10037 (10)0.0418 (4)
O30.69644 (8)0.2930 (3)0.34758 (12)0.0332 (4)
O40.65080 (10)0.1545 (4)0.17649 (13)0.0410 (5)
O50.49928 (8)0.1655 (3)0.32986 (11)0.0335 (4)
O60.41846 (7)0.2822 (3)0.14309 (11)0.0306 (4)
C70.65465 (11)0.1541 (4)0.25954 (16)0.0260 (5)
C80.60086 (12)0.0536 (4)0.25571 (16)0.0264 (5)
C90.51829 (11)0.0478 (4)0.21401 (15)0.0247 (5)
C100.47427 (10)0.1533 (4)0.23147 (15)0.0238 (5)
H1N0.419400.394300.538000.042 (7)*
H20.422700.536300.398500.053 (8)*
H2N0.264800.957000.382400.044 (7)*
H30.323500.641100.529000.040 (6)*
H3A0.168300.692900.129200.040 (7)*
H3B0.150200.967600.107100.039 (7)*
H3C0.130000.801200.013500.037 (6)*
H4A0.292001.152300.265900.030 (6)*
H4B0.361201.044200.276800.024 (5)*
H50.246101.008400.091500.027 (6)*
H220.3808 (19)0.515 (8)0.167 (3)0.070 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0397 (7)0.0217 (7)0.0427 (8)0.0002 (6)0.0290 (7)0.0044 (7)
O20.0302 (7)0.0336 (8)0.0455 (8)0.0028 (7)0.0270 (6)0.0092 (7)
N10.0302 (8)0.0370 (10)0.0224 (7)0.0094 (8)0.0154 (6)0.0083 (8)
N20.0260 (7)0.0320 (9)0.0254 (7)0.0038 (7)0.0189 (6)0.0004 (7)
N30.0239 (7)0.0292 (8)0.0245 (7)0.0054 (7)0.0165 (6)0.0032 (7)
C10.0202 (7)0.0282 (10)0.0201 (8)0.0001 (8)0.0136 (7)0.0031 (8)
C20.0261 (9)0.0381 (11)0.0250 (8)0.0080 (9)0.0176 (7)0.0032 (9)
C30.0277 (9)0.0410 (11)0.0227 (8)0.0011 (10)0.0170 (7)0.0015 (9)
C40.0274 (8)0.0200 (9)0.0278 (8)0.0004 (8)0.0204 (7)0.0027 (8)
C50.0260 (8)0.0201 (9)0.0223 (8)0.0027 (7)0.0183 (7)0.0034 (7)
C60.0289 (8)0.0219 (9)0.0220 (8)0.0040 (8)0.0189 (7)0.0030 (7)
F10.0287 (5)0.0398 (7)0.0408 (6)0.0082 (6)0.0240 (5)0.0160 (6)
F20.0580 (8)0.0317 (7)0.0672 (9)0.0153 (7)0.0511 (7)0.0202 (7)
F30.0308 (6)0.0250 (6)0.0497 (7)0.0006 (5)0.0259 (5)0.0063 (6)
F40.0343 (6)0.0516 (9)0.0268 (6)0.0053 (6)0.0156 (5)0.0129 (6)
O30.0351 (7)0.0342 (8)0.0360 (7)0.0132 (6)0.0264 (6)0.0099 (7)
O40.0517 (8)0.0473 (10)0.0434 (8)0.0181 (8)0.0399 (7)0.0113 (8)
O50.0310 (6)0.0467 (9)0.0249 (6)0.0063 (7)0.0198 (6)0.0098 (7)
O60.0264 (6)0.0339 (8)0.0271 (6)0.0089 (6)0.0164 (6)0.0004 (6)
C70.0255 (8)0.0251 (9)0.0335 (9)0.0018 (8)0.0224 (8)0.0009 (8)
C80.0299 (9)0.0238 (9)0.0320 (9)0.0029 (8)0.0235 (8)0.0022 (8)
C90.0234 (8)0.0251 (9)0.0207 (8)0.0022 (8)0.0130 (7)0.0009 (7)
C100.0183 (7)0.0277 (10)0.0244 (8)0.0013 (8)0.0140 (7)0.0047 (8)
Geometric parameters (Å, º) top
F1—C81.358 (2)N2—H2N0.9332
F2—C81.355 (3)N3—H3B0.8978
F3—C91.348 (2)N3—H3C0.9185
F4—C91.353 (2)N3—H3A0.9085
O1—C61.199 (3)C1—C41.490 (3)
O2—C61.310 (3)C1—C21.349 (3)
O2—H220.92 (5)C4—C51.529 (2)
O3—C71.236 (2)C5—C61.512 (3)
O4—C71.237 (3)C2—H20.8974
O5—C101.230 (2)C3—H30.9035
O6—C101.244 (2)C4—H4B0.9509
N1—C31.316 (4)C4—H4A0.9698
N1—C21.377 (3)C5—H50.8895
N2—C31.316 (3)C7—C81.560 (4)
N2—C11.384 (3)C8—C91.540 (4)
N3—C51.497 (3)C9—C101.557 (4)
N1—H1N0.8451
F1···C3i3.368 (3)N2···N12.135 (3)
F1···C3ii3.290 (3)N2···C7x3.416 (3)
F1···O3iii3.124 (2)N2···F1x3.181 (3)
F1···F32.829 (2)N2···O3xi2.690 (3)
F1···O32.649 (2)N3···O6vii2.775 (2)
F1···C3iv3.187 (3)N3···O4xi3.079 (3)
F1···O52.862 (3)N3···O12.683 (3)
F1···N2iv3.181 (3)N3···F2x3.062 (3)
F2···N3iv3.062 (3)N3···O4x2.958 (3)
F2···F42.647 (2)C1···O23.256 (3)
F2···O63.183 (3)C2···C2ii3.572 (4)
F2···C7iii3.259 (3)C2···C63.323 (2)
F2···O3iii3.084 (2)C2···O23.244 (3)
F2···O42.637 (3)C2···C4v3.585 (3)
F3···O6v2.983 (2)C3···F1ii3.290 (3)
F3···O32.897 (3)C3···F1x3.187 (3)
F3···O52.696 (2)C3···C7x3.369 (3)
F3···F12.829 (2)C3···F3ix2.862 (2)
F3···C10v3.134 (2)C3···O3ix3.158 (3)
F3···C3i2.862 (2)C3···F1ix3.368 (3)
F3···O2v2.991 (3)C3···O3x3.159 (3)
F3···N1i3.083 (2)C4···C2iii3.585 (3)
F4···F22.647 (2)C4···O1iii3.229 (2)
F4···O62.622 (2)C4···O4xi3.359 (4)
F1···H3ii2.8168C5···O1vii3.360 (3)
F2···H3Biv2.7065C5···O6vii3.337 (2)
F2···H3Aiv2.5718C5···O1iii3.040 (3)
F3···H22v2.78 (5)C6···C23.323 (2)
F3···H3i2.5351C6···O63.310 (3)
F4···H3Cvi2.6907C6···O1vii3.145 (3)
O1···C5v3.040 (3)C7···C3iv3.369 (3)
O1···C4v3.229 (2)C7···F2v3.259 (3)
O1···N32.683 (3)C7···N2iv3.416 (3)
O1···C5vi3.360 (3)C9···O2v3.398 (3)
O1···C6vi3.145 (3)C10···O2v3.208 (3)
O1···O2vi3.204 (2)C10···O23.286 (3)
O1···O6vii3.231 (2)C10···F3iii3.134 (2)
O2···O1vii3.204 (2)C1···H3A2.9338
O2···C10iii3.208 (3)C2···H4Av2.9183
O2···F3iii2.991 (3)C2···H2ii3.0528
O2···C103.286 (3)C6···H5vi3.0206
O2···O62.544 (3)C7···H3Aiv2.8647
O2···C13.256 (3)C7···H3Bviii3.0178
O2···C23.244 (3)C7···H2Nviii2.6879
O2···C9iii3.398 (3)C10···H222.42 (4)
O3···F32.897 (3)C10···H1Nii2.9187
O3···F2v3.084 (2)C10···H4Bv3.0495
O3···C3i3.158 (3)C10···H3Cvi2.9226
O3···F1v3.124 (2)H1N···O5ii1.9558
O3···C3iv3.159 (3)H1N···C10ii2.9187
O3···F12.649 (2)H2···C2ii3.0528
O3···N2viii2.690 (3)H2···O22.8327
O4···F22.637 (3)H2N···C7xi2.6879
O4···N3iv2.958 (3)H2N···O3xi1.7568
O4···C4viii3.359 (4)H2N···H4A2.4719
O4···N3viii3.079 (3)H3···F1ii2.8168
O5···N1ii2.796 (2)H3···F3ix2.5351
O5···F12.862 (3)H3···O3ix2.2647
O5···F32.696 (2)H3A···C12.9338
O6···F42.622 (2)H3A···F2x2.5718
O6···C63.310 (3)H3A···O4x2.0639
O6···F3iii2.983 (2)H3A···O12.6063
O6···F23.183 (3)H3A···C7x2.8647
O6···N3vi2.775 (2)H3B···H4A2.5015
O6···O22.544 (3)H3B···F2x2.7065
O6···C5vi3.337 (2)H3B···C7xi3.0178
O6···O1vi3.231 (2)H3B···O4xi2.2185
O1···H5v2.2868H3C···O6vii1.8904
O1···H3C2.6400H3C···C10vii2.9226
O1···H5vi2.7565H3C···F4vii2.6907
O1···H4Av2.8580H3C···O12.6400
O1···H3A2.6063H4A···C2iii2.9183
O2···H4B2.5244H4A···H2N2.4719
O2···H22.8327H4A···O1iii2.8580
O3···H3i2.2647H4A···O4xi2.5791
O3···H2Nviii1.7568H4A···H3B2.5015
O4···H4Aviii2.5791H4B···O5iii2.6125
O4···H3Aiv2.0639H4B···O22.5244
O4···H3Bviii2.2185H4B···C10iii3.0495
O5···H4Bv2.6125H5···O1iii2.2868
O5···H222.74 (4)H5···O1vii2.7565
O5···H1Nii1.9558H5···C6vii3.0206
O6···H221.63 (5)H22···O61.63 (5)
O6···H3Cvi1.8904H22···C102.42 (4)
N1···N22.135 (3)H22···F3iii2.78 (5)
N1···O5ii2.796 (2)H22···O52.74 (4)
N1···F3ix3.083 (2)
C6—O2—H22112 (3)N2—C3—H3121.55
C2—N1—C3108.9 (2)C1—C4—H4A109.62
C1—N2—C3109.5 (2)C1—C4—H4B109.40
C3—N1—H1N124.92C5—C4—H4A111.33
C2—N1—H1N125.73C5—C4—H4B107.12
C3—N2—H2N126.99H4A—C4—H4B103.76
C1—N2—H2N123.25N3—C5—H5106.84
C5—N3—H3A111.49C4—C5—H5105.66
C5—N3—H3B110.68C6—C5—H5109.75
C5—N3—H3C110.75O3—C7—O4129.3 (3)
H3B—N3—H3C108.66O3—C7—C8114.3 (2)
H3A—N3—H3B106.16O4—C7—C8116.44 (19)
H3A—N3—H3C108.97F1—C8—F2106.61 (17)
N2—C1—C2105.74 (19)F1—C8—C7109.18 (18)
N2—C1—C4121.6 (2)F1—C8—C9107.6 (2)
C2—C1—C4132.6 (2)F2—C8—C7110.9 (2)
N1—C2—C1107.4 (2)F2—C8—C9107.05 (19)
N1—C3—N2108.5 (2)C7—C8—C9115.11 (18)
C1—C4—C5114.98 (17)F3—C9—F4106.63 (16)
C4—C5—C6112.92 (17)F3—C9—C8108.04 (18)
N3—C5—C4112.7 (2)F3—C9—C10110.3 (2)
N3—C5—C6108.74 (18)F4—C9—C8107.3 (2)
O1—C6—C5122.9 (2)F4—C9—C10111.41 (18)
O2—C6—C5111.01 (18)C8—C9—C10112.95 (17)
O1—C6—O2126.1 (2)O5—C10—O6128.7 (2)
N1—C2—H2121.09O5—C10—C9116.38 (18)
C1—C2—H2131.53O6—C10—C9114.90 (17)
N1—C3—H3129.49
C2—N1—C3—N20.4 (3)O4—C7—C8—F1138.9 (2)
C3—N1—C2—C10.2 (3)O4—C7—C8—F221.8 (3)
C3—N2—C1—C4178.21 (19)O4—C7—C8—C999.9 (3)
C1—N2—C3—N10.5 (3)F1—C8—C9—F373.8 (2)
C3—N2—C1—C20.4 (2)F1—C8—C9—F4171.54 (16)
N2—C1—C4—C5102.7 (2)F1—C8—C9—C1048.4 (2)
C4—C1—C2—N1178.2 (2)F2—C8—C9—F3171.88 (17)
N2—C1—C2—N10.1 (2)F2—C8—C9—F457.3 (2)
C2—C1—C4—C579.2 (3)F2—C8—C9—C1065.9 (2)
C1—C4—C5—N367.1 (3)C7—C8—C9—F348.1 (2)
C1—C4—C5—C656.6 (3)C7—C8—C9—F466.5 (2)
N3—C5—C6—O19.2 (3)C7—C8—C9—C10170.36 (15)
N3—C5—C6—O2171.53 (15)F3—C9—C10—O539.5 (3)
C4—C5—C6—O1135.1 (2)F3—C9—C10—O6141.1 (2)
C4—C5—C6—O245.7 (3)F4—C9—C10—O5157.6 (2)
O3—C7—C8—F139.9 (3)F4—C9—C10—O622.9 (3)
O3—C7—C8—F2157.1 (2)C8—C9—C10—O581.5 (2)
O3—C7—C8—C981.2 (2)C8—C9—C10—O697.9 (2)
Symmetry codes: (i) x+1, y1, z+1; (ii) x+1, y, z+1; (iii) x, y+1, z; (iv) x+1/2, y1/2, z; (v) x, y1, z; (vi) x+1/2, y1/2, z; (vii) x+1/2, y+1/2, z; (viii) x+1/2, y3/2, z; (ix) x+1, y+1, z+1; (x) x1/2, y+1/2, z; (xi) x1/2, y+3/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O5ii0.851.962.796 (2)172
N2—H2N···O3xi0.931.762.690 (3)179
N3—H3A···O4x0.912.062.958 (3)168
N3—H3B···O4xi0.902.223.079 (3)160
N3—H3C···O6vii0.921.892.775 (2)161
O2—H22···O60.92 (5)1.63 (5)2.544 (3)171 (4)
C3—H3···F3ix0.902.542.862 (2)102
C3—H3···O3ix0.902.263.158 (3)170
C4—H4A···O4xi0.972.583.359 (4)138
C5—H5···O1iii0.892.293.040 (3)142
Symmetry codes: (ii) x+1, y, z+1; (iii) x, y+1, z; (vii) x+1/2, y+1/2, z; (ix) x+1, y+1, z+1; (x) x1/2, y+1/2, z; (xi) x1/2, y+3/2, z.
 

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