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In the title salt, C19H18N3+·C2F3O2-, the anion exhibits rotational disorder of the CF3 group. The structure is stabilized by hydrogen bonds where the O atoms of the anion are acceptors from the NH guanidinium groups, forming infinite chains that run along the [001] direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806055899/bt2230sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806055899/bt2230Isup2.hkl
Contains datablock I

CCDC reference: 636163

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.009 Å
  • Disorder in solvent or counterion
  • R factor = 0.073
  • wR factor = 0.247
  • Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 42 Perc. PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent ......... 3 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C21 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 23.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 43.00 Deg. F3B -C22 -F2C 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 17.60 Deg. F1B -C22 -F1A 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 29.20 Deg. F2C -C22 -F2A 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 29.90 Deg. F1A -C22 -F1C 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 34.70 Deg. F2A -C22 -F2B 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 33.50 Deg. F3B -C22 -F3A 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 25.30 Deg. F3C -C22 -F3A 1.555 1.555 1.555
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: SDP-Plus (Frenz, 1985); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

N,N',N''-Triphenylguanidinium trifluoroacetate top
Crystal data top
C19H18N3+·C2F3O2F(000) = 832
Mr = 401.38Dx = 1.305 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 9.9905 (8) Åθ = 7.6–12.7°
b = 14.9348 (13) ŵ = 0.10 mm1
c = 14.1194 (10) ÅT = 293 K
β = 104.052 (9)°Plate, colourless
V = 2043.7 (3) Å30.29 × 0.20 × 0.12 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.086
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 2.5°
Graphite monochromatorh = 1111
Profile data from ω–2θ scansk = 017
7224 measured reflectionsl = 1616
3601 independent reflections3 standard reflections every 180 min
1507 reflections with I > 2σ(I) intensity decay: 2%
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)] = 0.073Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.247H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.1036P)2 + 1.7521P]
where P = (Fo2 + 2Fc2)/3
3601 reflections(Δ/σ)max = 0.006
268 parametersΔρmax = 0.57 e Å3
16 restraintsΔρmin = 0.45 e Å3
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)
N10.6345 (4)0.1990 (3)0.1016 (3)0.0612 (13)
H10.58720.19350.14470.073*
N20.8094 (4)0.2767 (3)0.0573 (3)0.0527 (12)
H20.75790.28240.00080.063*
N30.7951 (4)0.2680 (3)0.2213 (3)0.0608 (13)
H30.77750.23020.26260.073*
C10.7485 (5)0.2480 (4)0.1270 (3)0.0505 (13)
C20.8705 (5)0.3451 (4)0.2602 (3)0.0523 (13)
C30.8500 (6)0.4260 (4)0.2133 (4)0.0667 (16)
H3A0.78890.43070.15220.080*
C40.9197 (8)0.4998 (5)0.2564 (5)0.093 (2)
H40.90670.55450.22410.112*
C51.0086 (8)0.4940 (5)0.3468 (6)0.100 (2)
H51.05540.54460.37580.120*
C61.0283 (7)0.4141 (6)0.3941 (5)0.082 (2)
H61.08860.41030.45560.099*
C70.9598 (6)0.3386 (4)0.3519 (4)0.0665 (16)
H70.97340.28400.38450.080*
C80.9513 (5)0.2984 (4)0.0714 (3)0.0459 (12)
C90.9874 (6)0.3649 (4)0.0155 (4)0.0617 (15)
H90.91910.39640.02830.074*
C101.1248 (7)0.3856 (5)0.0238 (5)0.0807 (19)
H101.14910.43040.01470.097*
C111.2241 (7)0.3396 (6)0.0888 (6)0.089 (2)
H111.31650.35400.09540.106*
C121.1902 (6)0.2735 (5)0.1436 (5)0.0777 (19)
H121.25950.24220.18680.093*
C131.0526 (6)0.2514 (4)0.1363 (4)0.0611 (15)
H131.02940.20590.17440.073*
C140.5813 (5)0.1541 (4)0.0107 (4)0.0547 (14)
C150.4427 (6)0.1611 (4)0.0314 (4)0.0700 (17)
H150.38660.19580.00220.084*
C160.3870 (7)0.1160 (5)0.1174 (5)0.095 (2)
H160.29290.12020.14560.114*
C170.4674 (9)0.0658 (5)0.1614 (5)0.096 (2)
H170.42890.03650.21980.116*
C180.6050 (8)0.0585 (5)0.1196 (5)0.084 (2)
H180.66040.02370.14930.101*
C190.6626 (6)0.1027 (4)0.0334 (4)0.0722 (17)
H190.75670.09770.00530.087*
O10.4898 (4)0.1658 (3)0.2411 (3)0.0703 (12)
O20.6793 (4)0.1837 (3)0.3602 (2)0.0600 (11)
C210.5603 (6)0.1571 (4)0.3251 (4)0.0514 (13)
C220.4950 (6)0.1014 (4)0.3951 (4)0.0728 (18)
F1A0.5424 (9)0.1226 (6)0.4868 (5)0.0676 (14)*0.506 (4)
F2A0.4905 (12)0.0161 (4)0.3728 (6)0.0676 (14)*0.506 (4)
F3A0.3521 (6)0.1280 (6)0.3736 (6)0.0676 (14)*0.506 (4)
F1B0.5099 (14)0.1389 (9)0.4797 (7)0.082 (3)*0.314 (10)
F2B0.5660 (15)0.0222 (7)0.4078 (10)0.082 (3)*0.314 (10)
F3B0.3731 (11)0.0770 (12)0.3692 (9)0.082 (3)*0.314 (10)
F1C0.5788 (18)0.0854 (17)0.4815 (10)0.084 (6)*0.179 (10)
F2C0.429 (3)0.0325 (13)0.3542 (13)0.084 (6)*0.179 (10)
F3C0.3884 (19)0.1373 (13)0.4144 (18)0.084 (6)*0.179 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.057 (3)0.093 (3)0.036 (2)0.020 (3)0.015 (2)0.000 (2)
N20.048 (3)0.077 (3)0.032 (2)0.009 (2)0.0078 (19)0.008 (2)
N30.066 (3)0.081 (3)0.037 (2)0.020 (3)0.016 (2)0.003 (2)
C10.052 (3)0.066 (3)0.034 (3)0.005 (3)0.011 (2)0.005 (2)
C20.048 (3)0.071 (4)0.040 (3)0.006 (3)0.015 (2)0.003 (3)
C30.072 (4)0.074 (4)0.047 (3)0.009 (3)0.002 (3)0.004 (3)
C40.121 (6)0.068 (5)0.076 (5)0.005 (4)0.007 (4)0.005 (4)
C50.109 (6)0.083 (5)0.088 (5)0.015 (4)0.015 (4)0.020 (4)
C60.076 (4)0.110 (6)0.049 (3)0.005 (4)0.009 (3)0.013 (4)
C70.066 (4)0.086 (4)0.043 (3)0.004 (3)0.006 (3)0.001 (3)
C80.053 (3)0.053 (3)0.034 (3)0.005 (3)0.016 (2)0.003 (2)
C90.070 (4)0.069 (4)0.050 (3)0.002 (3)0.022 (3)0.004 (3)
C100.080 (5)0.088 (5)0.088 (5)0.018 (4)0.047 (4)0.003 (4)
C110.058 (4)0.117 (6)0.098 (5)0.012 (4)0.032 (4)0.022 (5)
C120.056 (4)0.102 (6)0.071 (4)0.014 (4)0.009 (3)0.007 (4)
C130.059 (4)0.069 (4)0.056 (3)0.007 (3)0.014 (3)0.006 (3)
C140.055 (3)0.069 (4)0.040 (3)0.015 (3)0.010 (2)0.001 (3)
C150.052 (3)0.096 (5)0.063 (4)0.012 (3)0.015 (3)0.018 (3)
C160.066 (4)0.131 (7)0.080 (5)0.026 (4)0.005 (4)0.029 (5)
C170.102 (6)0.117 (6)0.069 (5)0.027 (5)0.018 (4)0.036 (4)
C180.104 (6)0.088 (5)0.065 (4)0.001 (4)0.030 (4)0.020 (4)
C190.063 (4)0.086 (5)0.068 (4)0.006 (3)0.016 (3)0.005 (4)
O10.053 (2)0.112 (3)0.045 (2)0.008 (2)0.0091 (18)0.003 (2)
O20.052 (2)0.090 (3)0.038 (2)0.018 (2)0.0094 (17)0.0027 (18)
C210.056 (3)0.067 (4)0.034 (3)0.003 (3)0.017 (3)0.003 (3)
C220.074 (4)0.093 (5)0.050 (3)0.013 (4)0.012 (3)0.014 (3)
Geometric parameters (Å, º) top
N1—C11.329 (6)C11—H110.9300
N1—C141.430 (6)C12—C131.393 (8)
N1—H10.8600C12—H120.9300
N2—C11.346 (6)C13—H130.9300
N2—C81.420 (6)C14—C151.372 (7)
N2—H20.8600C14—C191.372 (8)
N3—C11.334 (6)C15—C161.382 (8)
N3—C21.411 (6)C15—H150.9300
N3—H30.8600C16—C171.354 (9)
C2—C31.370 (8)C16—H160.9300
C2—C71.386 (7)C17—C181.362 (9)
C3—C41.365 (8)C17—H170.9300
C3—H3A0.9300C18—C191.381 (8)
C4—C51.370 (9)C18—H180.9300
C4—H40.9300C19—H190.9300
C5—C61.358 (10)O1—C211.231 (6)
C5—H50.9300O2—C211.237 (6)
C6—C71.377 (8)C21—C221.552 (8)
C6—H60.9300C22—F3B1.239 (8)
C7—H70.9300C22—F3C1.279 (10)
C8—C91.371 (7)C22—F2C1.281 (10)
C8—C131.381 (7)C22—F1B1.295 (9)
C9—C101.383 (8)C22—F1A1.306 (8)
C9—H90.9300C22—F2A1.310 (7)
C10—C111.362 (9)C22—F1C1.323 (10)
C10—H100.9300C22—F2B1.368 (9)
C11—C121.348 (9)C22—F3A1.442 (7)
C1—N1—C14127.4 (4)C16—C17—C18119.6 (7)
C1—N1—H1116.3C16—C17—H17120.2
C14—N1—H1116.3C18—C17—H17120.2
C1—N2—C8125.7 (4)C17—C18—C19120.3 (6)
C1—N2—H2117.2C17—C18—H18119.9
C8—N2—H2117.2C19—C18—H18119.9
C1—N3—C2126.5 (4)C14—C19—C18120.1 (6)
C1—N3—H3116.8C14—C19—H19120.0
C2—N3—H3116.8C18—C19—H19120.0
N1—C1—N3117.5 (4)O1—C21—O2128.5 (5)
N1—C1—N2119.2 (4)O1—C21—C22116.1 (5)
N3—C1—N2123.3 (5)O2—C21—C22115.3 (4)
C3—C2—C7120.0 (5)F3B—C22—F3C51.5 (11)
C3—C2—N3121.9 (5)F3B—C22—F2C43.0 (11)
C7—C2—N3117.9 (5)F3C—C22—F2C93.9 (14)
C4—C3—C2119.7 (5)F3B—C22—F1B106.6 (10)
C4—C3—H3A120.1F3C—C22—F1B62.4 (13)
C2—C3—H3A120.1F2C—C22—F1B134.0 (12)
C3—C4—C5120.7 (7)F3B—C22—F1A117.3 (8)
C3—C4—H4119.7F3C—C22—F1A78.9 (12)
C5—C4—H4119.7F2C—C22—F1A131.7 (10)
C6—C5—C4119.8 (7)F1B—C22—F1A17.6 (8)
C6—C5—H5120.1F3B—C22—F2A70.6 (8)
C4—C5—H5120.1F3C—C22—F2A118.5 (11)
C5—C6—C7120.6 (6)F2C—C22—F2A29.2 (12)
C5—C6—H6119.7F1B—C22—F2A129.2 (8)
C7—C6—H6119.7F1A—C22—F2A117.2 (6)
C6—C7—C2119.1 (6)F3B—C22—F1C125.2 (11)
C6—C7—H7120.4F3C—C22—F1C104.6 (13)
C2—C7—H7120.4F2C—C22—F1C114.3 (14)
C9—C8—C13119.8 (5)F1B—C22—F1C47.4 (12)
C9—C8—N2118.6 (5)F1A—C22—F1C29.9 (11)
C13—C8—N2121.5 (5)F2A—C22—F1C91.3 (11)
C8—C9—C10120.5 (6)F3B—C22—F2B103.0 (9)
C8—C9—H9119.8F3C—C22—F2B140.0 (11)
C10—C9—H9119.8F2C—C22—F2B63.8 (13)
C11—C10—C9119.3 (6)F1B—C22—F2B108.3 (9)
C11—C10—H10120.3F1A—C22—F2B91.7 (7)
C9—C10—H10120.3F2A—C22—F2B34.7 (5)
C12—C11—C10120.8 (6)F1C—C22—F2B62.1 (12)
C12—C11—H11119.6F3B—C22—F3A33.5 (7)
C10—C11—H11119.6F3C—C22—F3A25.3 (11)
C11—C12—C13120.8 (6)F2C—C22—F3A75.6 (13)
C11—C12—H12119.6F1B—C22—F3A87.8 (8)
C13—C12—H12119.6F1A—C22—F3A104.1 (6)
C8—C13—C12118.7 (6)F2A—C22—F3A104.0 (6)
C8—C13—H13120.7F1C—C22—F3A128.1 (11)
C12—C13—H13120.7F2B—C22—F3A136.1 (7)
C15—C14—C19119.5 (5)F3B—C22—C21120.3 (7)
C15—C14—N1117.9 (5)F3C—C22—C21114.2 (9)
C19—C14—N1122.5 (5)F2C—C22—C21113.2 (9)
C14—C15—C16119.5 (6)F1B—C22—C21112.5 (7)
C14—C15—H15120.3F1A—C22—C21113.2 (6)
C16—C15—H15120.3F2A—C22—C21111.3 (5)
C17—C16—C15121.0 (7)F1C—C22—C21114.5 (8)
C17—C16—H16119.5F2B—C22—C21105.2 (6)
C15—C16—H16119.5F3A—C22—C21105.4 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.861.902.756 (5)173
N2—H2···O2i0.861.992.833 (5)165
N3—H3···O20.862.002.806 (5)156
Symmetry code: (i) x, y+1/2, z1/2.
 

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