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In the title compound, C6H16N4O22+·2C2F3O2-, the cations have their amino, guanidyl and carboxylate groups protonated, thus featuring a double positive charge. One of the anions shows rotational disorder of its CF3 group. A network of hydrogen bonds links the ions together, utilizing all possible arginine donor atoms.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803025169/bt6374sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803025169/bt6374Isup2.hkl
Contains datablock I

CCDC reference: 227877

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.044
  • wR factor = 0.134
  • Data-to-parameter ratio = 9.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... C4 PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... C2
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.14 PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.28 PLAT301_ALERT_3_C Main Residue Disorder ......................... 10.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT414_ALERT_2_C Short Intra D-H..H-X H1A .. H6A = 1.99 Ang. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 20.30 Deg. F6A -C4 -F6B 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 35.00 Deg. F5A -C4 -F5B 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 23.00 Deg. F4B -C4 -F4A 1.555 1.555 1.555 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C6 H16 N4 O2 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C2 F3 O2 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 C2 F3 O2
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 30.06 From the CIF: _reflns_number_total 2610 Count of symmetry unique reflns 2612 Completeness (_total/calc) 99.92% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

L-argininium bis(trifluoroacetate) top
Crystal data top
C6H16N4O22+·2C2F3O2F(000) = 412
Mr = 402.27Dx = 1.629 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 9.8457 (9) ÅCell parameters from 25 reflections
b = 5.7677 (13) Åθ = 6.7–16.3°
c = 14.5035 (12) ŵ = 0.17 mm1
β = 95.178 (7)°T = 293 K
V = 820.2 (2) Å3Prism, colourless
Z = 20.51 × 0.41 × 0.25 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.024
Radiation source: fine-focus sealed tubeθmax = 30.1°, θmin = 3.4°
Graphite monochromatorh = 013
profile data from ω–2θ scansk = 08
2752 measured reflectionsl = 2020
2610 independent reflections3 standard reflections every 180 min
1917 reflections with I > 2σ(I) intensity decay: 2%
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)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.134 w = 1/[σ2(Fo2) + (0.0673P)2 + 0.2789P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
2610 reflectionsΔρmax = 0.28 e Å3
267 parametersΔρmin = 0.27 e Å3
7 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.028 (6)
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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*/UeqOcc. (<1)
C20.3387 (4)1.1271 (9)0.9752 (3)0.0616 (10)
F10.4216 (4)1.0958 (8)0.9110 (3)0.143 (2)
F20.2754 (4)0.9312 (6)0.9887 (3)0.1064 (11)
F30.4166 (3)1.1577 (9)1.0540 (2)0.1139 (13)
C40.1793 (4)1.3462 (7)0.4714 (2)0.0491 (8)
F4A0.2761 (9)1.4485 (14)0.4257 (6)0.084 (3)0.67 (3)
F5A0.1319 (15)1.5163 (15)0.5190 (7)0.089 (3)0.67 (3)
F6A0.0905 (9)1.262 (2)0.4118 (7)0.104 (3)0.67 (3)
F4B0.250 (3)1.509 (5)0.445 (2)0.132 (10)0.33 (3)
F5B0.069 (3)1.431 (7)0.5075 (18)0.120 (11)0.33 (3)
F6B0.121 (3)1.278 (4)0.3912 (13)0.124 (9)0.33 (3)
O10.2535 (3)1.4434 (5)0.88721 (15)0.0536 (6)
O20.1533 (3)1.3506 (6)1.01224 (18)0.0637 (8)
O30.2128 (2)1.1388 (5)0.61293 (14)0.0484 (6)
O40.3303 (3)1.0341 (5)0.49560 (18)0.0588 (7)
O51.0189 (3)1.0374 (5)0.7790 (2)0.0580 (7)
O61.0483 (2)1.3696 (5)0.70705 (15)0.0455 (6)
H61.08751.28780.67160.068*
N10.4510 (3)1.6680 (6)0.61175 (18)0.0517 (8)
H1A0.51611.59110.59030.062*
H1B0.41441.78290.58090.062*
N20.3086 (3)1.7338 (6)0.72389 (19)0.0459 (7)
H2A0.27431.84960.69260.055*
H2B0.27881.69840.77600.055*
N30.4601 (3)1.4348 (6)0.74195 (17)0.0409 (6)
H30.44241.42910.79890.049*
N40.9737 (2)1.6019 (5)0.85628 (19)0.0405 (6)
H4A0.97841.69010.80630.061*
H4B1.05741.57560.88270.061*
H4C0.92481.67430.89630.061*
C10.2393 (3)1.3269 (6)0.9563 (2)0.0445 (8)
C30.2473 (3)1.1546 (6)0.5323 (2)0.0398 (7)
C50.4075 (3)1.6098 (6)0.69182 (19)0.0342 (6)
C60.5458 (3)1.2497 (7)0.7093 (2)0.0461 (8)
H6A0.56841.28690.64730.055*
H6B0.49431.10600.70600.055*
C70.6763 (3)1.2140 (6)0.7711 (2)0.0400 (7)
H7A0.72531.08330.74820.048*
H7B0.65361.17600.83300.048*
C80.7686 (3)1.4251 (6)0.7760 (2)0.0374 (6)
H8A0.72411.55050.80620.045*
H8B0.78221.47490.71360.045*
C90.9075 (3)1.3774 (6)0.82880 (18)0.0327 (6)
H90.89401.28780.88470.039*
C100.9990 (3)1.2405 (5)0.76937 (19)0.0336 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.067 (2)0.059 (2)0.062 (2)0.010 (2)0.0277 (18)0.018 (2)
F10.162 (3)0.146 (4)0.139 (3)0.095 (3)0.111 (3)0.077 (3)
F20.127 (3)0.0490 (16)0.149 (3)0.0052 (18)0.044 (2)0.0200 (19)
F30.0838 (18)0.139 (4)0.112 (2)0.016 (2)0.0277 (17)0.034 (3)
C40.0593 (19)0.050 (2)0.0395 (15)0.0033 (18)0.0130 (14)0.0014 (16)
F4A0.100 (4)0.072 (5)0.088 (3)0.015 (3)0.050 (4)0.047 (3)
F5A0.137 (8)0.064 (4)0.071 (3)0.054 (4)0.035 (5)0.016 (3)
F6A0.086 (4)0.125 (7)0.091 (5)0.035 (4)0.049 (4)0.030 (5)
F4B0.114 (13)0.056 (10)0.21 (2)0.041 (10)0.055 (13)0.053 (12)
F5B0.142 (17)0.13 (2)0.090 (11)0.104 (16)0.054 (13)0.054 (13)
F6B0.23 (2)0.088 (12)0.047 (6)0.056 (14)0.019 (9)0.024 (7)
O10.0623 (14)0.0557 (16)0.0438 (11)0.0004 (13)0.0107 (10)0.0153 (12)
O20.0635 (15)0.0657 (19)0.0667 (15)0.0102 (16)0.0311 (13)0.0180 (16)
O30.0533 (12)0.0558 (15)0.0394 (10)0.0159 (12)0.0212 (9)0.0077 (11)
O40.0723 (16)0.0508 (15)0.0599 (14)0.0161 (14)0.0418 (13)0.0090 (13)
O50.0748 (18)0.0315 (12)0.0724 (17)0.0103 (13)0.0324 (14)0.0063 (12)
O60.0559 (12)0.0404 (12)0.0438 (11)0.0131 (12)0.0243 (9)0.0075 (10)
N10.0562 (15)0.0546 (19)0.0482 (14)0.0108 (15)0.0262 (12)0.0097 (14)
N20.0445 (13)0.0471 (16)0.0494 (14)0.0087 (13)0.0219 (11)0.0127 (13)
N30.0405 (12)0.0471 (15)0.0357 (11)0.0046 (12)0.0071 (10)0.0005 (12)
N40.0366 (12)0.0316 (13)0.0546 (14)0.0035 (11)0.0107 (11)0.0046 (12)
C10.0493 (17)0.0439 (19)0.0406 (15)0.0068 (15)0.0062 (13)0.0088 (14)
C30.0410 (14)0.0407 (17)0.0399 (14)0.0031 (14)0.0156 (12)0.0012 (14)
C50.0302 (11)0.0372 (15)0.0360 (12)0.0056 (12)0.0072 (10)0.0009 (12)
C60.0442 (16)0.0433 (19)0.0501 (17)0.0060 (15)0.0000 (13)0.0090 (16)
C70.0402 (14)0.0362 (16)0.0438 (15)0.0005 (13)0.0056 (12)0.0007 (14)
C80.0359 (13)0.0347 (15)0.0427 (13)0.0045 (12)0.0093 (11)0.0058 (13)
C90.0351 (12)0.0307 (13)0.0340 (11)0.0018 (12)0.0113 (10)0.0015 (12)
C100.0353 (13)0.0315 (15)0.0350 (13)0.0045 (12)0.0083 (10)0.0003 (12)
Geometric parameters (Å, º) top
C2—F11.305 (4)N2—C51.326 (4)
C2—F21.313 (6)N2—H2A0.8600
C2—F31.330 (5)N2—H2B0.8600
C2—C11.520 (6)N3—C51.322 (4)
C4—F4B1.244 (14)N3—C61.466 (4)
C4—F6A1.269 (7)N3—H30.8600
C4—F6B1.308 (13)N4—C91.488 (4)
C4—F5A1.310 (9)N4—H4A0.8900
C4—F5B1.340 (15)N4—H4B0.8900
C4—F4A1.345 (7)N4—H4C0.8900
C4—C31.531 (5)C6—C71.513 (4)
O1—C11.225 (4)C6—H6A0.9700
O2—C11.232 (4)C6—H6B0.9700
O3—C31.251 (3)C7—C81.517 (4)
O4—C31.229 (4)C7—H7A0.9700
O5—C101.194 (4)C7—H7B0.9700
O6—C101.298 (4)C8—C91.531 (4)
O6—H60.8200C8—H8A0.9700
N1—C51.317 (4)C8—H8B0.9700
N1—H1A0.8600C9—C101.522 (4)
N1—H1B0.8600C9—H90.9800
F1—C2—F2108.9 (5)C9—N4—H4C109.5
F1—C2—F3106.4 (4)H4A—N4—H4C109.5
F2—C2—F3103.3 (4)H4B—N4—H4C109.5
F1—C2—C1114.2 (3)O1—C1—O2127.8 (4)
F2—C2—C1111.9 (3)O1—C1—C2116.4 (3)
F3—C2—C1111.4 (4)O2—C1—C2115.8 (3)
F4B—C4—F6A116.5 (12)O4—C3—O3127.6 (3)
F4B—C4—F6B99.3 (15)O4—C3—C4115.6 (3)
F6A—C4—F6B20.3 (15)O3—C3—C4116.8 (3)
F4B—C4—F5A80.3 (18)N1—C5—N3122.5 (3)
F6A—C4—F5A112.9 (7)N1—C5—N2118.7 (3)
F6B—C4—F5A123.1 (10)N3—C5—N2118.9 (2)
F4B—C4—F5B109.8 (14)N3—C6—C7113.0 (3)
F6A—C4—F5B82.7 (17)N3—C6—H6A109.0
F6B—C4—F5B98.9 (16)C7—C6—H6A109.0
F5A—C4—F5B35.0 (17)N3—C6—H6B109.0
F4B—C4—F4A23 (2)C7—C6—H6B109.0
F6A—C4—F4A107.9 (7)H6A—C6—H6B107.8
F6B—C4—F4A88.0 (15)C6—C7—C8113.1 (3)
F5A—C4—F4A103.5 (6)C6—C7—H7A109.0
F5B—C4—F4A131.9 (15)C8—C7—H7A109.0
F4B—C4—C3119.6 (12)C6—C7—H7B109.0
F6A—C4—C3110.9 (6)C8—C7—H7B109.0
F6B—C4—C3115.4 (10)H7A—C7—H7B107.8
F5A—C4—C3113.3 (5)C7—C8—C9112.5 (3)
F5B—C4—C3111.5 (10)C7—C8—H8A109.1
F4A—C4—C3107.9 (5)C9—C8—H8A109.1
C10—O6—H6109.5C7—C8—H8B109.1
C5—N1—H1A120.0C9—C8—H8B109.1
C5—N1—H1B120.0H8A—C8—H8B107.8
H1A—N1—H1B120.0N4—C9—C10109.6 (2)
C5—N2—H2A120.0N4—C9—C8109.1 (2)
C5—N2—H2B120.0C10—C9—C8110.9 (2)
H2A—N2—H2B120.0N4—C9—H9109.0
C5—N3—C6126.0 (2)C10—C9—H9109.0
C5—N3—H3117.0C8—C9—H9109.0
C6—N3—H3117.0O5—C10—O6125.2 (3)
C9—N4—H4A109.5O5—C10—C9122.8 (3)
C9—N4—H4B109.5O6—C10—C9112.0 (3)
H4A—N4—H4B109.5
F1—C2—C1—O14.3 (6)F5A—C4—C3—O322.8 (9)
F2—C2—C1—O1128.6 (4)F5B—C4—C3—O315 (2)
F3—C2—C1—O1116.2 (4)F4A—C4—C3—O3136.7 (5)
F1—C2—C1—O2175.0 (5)C6—N3—C5—N115.9 (5)
F2—C2—C1—O250.7 (5)C6—N3—C5—N2165.2 (3)
F3—C2—C1—O264.4 (5)C5—N3—C6—C7129.1 (3)
F4B—C4—C3—O465 (2)N3—C6—C7—C862.3 (4)
F6A—C4—C3—O474.8 (7)C6—C7—C8—C9172.9 (2)
F6B—C4—C3—O453.3 (17)C7—C8—C9—N4162.3 (2)
F5A—C4—C3—O4157.1 (8)C7—C8—C9—C1076.8 (3)
F5B—C4—C3—O4165 (2)N4—C9—C10—O5136.9 (4)
F4A—C4—C3—O443.1 (6)C8—C9—C10—O5102.6 (4)
F4B—C4—C3—O3115 (2)N4—C9—C10—O644.7 (3)
F6A—C4—C3—O3105.3 (7)C8—C9—C10—O675.8 (3)
F6B—C4—C3—O3126.8 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6···O3i0.821.782.581 (3)164
O6—H6···F5Bi0.822.512.94 (2)114
N1—H1A···O4ii0.862.072.874 (3)155
N1—H1B···O4iii0.862.032.889 (4)174
N2—H2A···O3iii0.862.092.943 (4)174
N2—H2B···O10.862.212.990 (4)150
N3—H3···O10.862.353.058 (3)139
N3—H3···F10.862.543.185 (4)133
N4—H4A···O5iii0.892.092.803 (4)137
N4—H4B···O1i0.892.072.899 (4)154
N4—H4B···O2i0.892.413.102 (4)135
N4—H4C···O2iv0.891.892.772 (4)171
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1/2, z+1; (iii) x, y+1, z; (iv) x+1, y+1/2, z+2.
 

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