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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
CCDC reference: 636163
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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+·C2F3O2− | F(000) = 832 |
Mr = 401.38 | Dx = 1.305 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 9.9905 (8) Å | θ = 7.6–12.7° |
b = 14.9348 (13) Å | µ = 0.10 mm−1 |
c = 14.1194 (10) Å | T = 293 K |
β = 104.052 (9)° | Plate, colourless |
V = 2043.7 (3) Å3 | 0.29 × 0.20 × 0.12 mm |
Z = 4 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.086 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.5° |
Graphite monochromator | h = −11→11 |
Profile data from ω–2θ scans | k = 0→17 |
7224 measured reflections | l = −16→16 |
3601 independent reflections | 3 standard reflections every 180 min |
1507 reflections with I > 2σ(I) | intensity decay: 2% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.073 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.247 | H-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 parameters | Δρmax = 0.57 e Å−3 |
16 restraints | Δρmin = −0.45 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
N1 | 0.6345 (4) | 0.1990 (3) | 0.1016 (3) | 0.0612 (13) | |
H1 | 0.5872 | 0.1935 | 0.1447 | 0.073* | |
N2 | 0.8094 (4) | 0.2767 (3) | 0.0573 (3) | 0.0527 (12) | |
H2 | 0.7579 | 0.2824 | −0.0008 | 0.063* | |
N3 | 0.7951 (4) | 0.2680 (3) | 0.2213 (3) | 0.0608 (13) | |
H3 | 0.7775 | 0.2302 | 0.2626 | 0.073* | |
C1 | 0.7485 (5) | 0.2480 (4) | 0.1270 (3) | 0.0505 (13) | |
C2 | 0.8705 (5) | 0.3451 (4) | 0.2602 (3) | 0.0523 (13) | |
C3 | 0.8500 (6) | 0.4260 (4) | 0.2133 (4) | 0.0667 (16) | |
H3A | 0.7889 | 0.4307 | 0.1522 | 0.080* | |
C4 | 0.9197 (8) | 0.4998 (5) | 0.2564 (5) | 0.093 (2) | |
H4 | 0.9067 | 0.5545 | 0.2241 | 0.112* | |
C5 | 1.0086 (8) | 0.4940 (5) | 0.3468 (6) | 0.100 (2) | |
H5 | 1.0554 | 0.5446 | 0.3758 | 0.120* | |
C6 | 1.0283 (7) | 0.4141 (6) | 0.3941 (5) | 0.082 (2) | |
H6 | 1.0886 | 0.4103 | 0.4556 | 0.099* | |
C7 | 0.9598 (6) | 0.3386 (4) | 0.3519 (4) | 0.0665 (16) | |
H7 | 0.9734 | 0.2840 | 0.3845 | 0.080* | |
C8 | 0.9513 (5) | 0.2984 (4) | 0.0714 (3) | 0.0459 (12) | |
C9 | 0.9874 (6) | 0.3649 (4) | 0.0155 (4) | 0.0617 (15) | |
H9 | 0.9191 | 0.3964 | −0.0283 | 0.074* | |
C10 | 1.1248 (7) | 0.3856 (5) | 0.0238 (5) | 0.0807 (19) | |
H10 | 1.1491 | 0.4304 | −0.0147 | 0.097* | |
C11 | 1.2241 (7) | 0.3396 (6) | 0.0888 (6) | 0.089 (2) | |
H11 | 1.3165 | 0.3540 | 0.0954 | 0.106* | |
C12 | 1.1902 (6) | 0.2735 (5) | 0.1436 (5) | 0.0777 (19) | |
H12 | 1.2595 | 0.2422 | 0.1868 | 0.093* | |
C13 | 1.0526 (6) | 0.2514 (4) | 0.1363 (4) | 0.0611 (15) | |
H13 | 1.0294 | 0.2059 | 0.1744 | 0.073* | |
C14 | 0.5813 (5) | 0.1541 (4) | 0.0107 (4) | 0.0547 (14) | |
C15 | 0.4427 (6) | 0.1611 (4) | −0.0314 (4) | 0.0700 (17) | |
H15 | 0.3866 | 0.1958 | −0.0022 | 0.084* | |
C16 | 0.3870 (7) | 0.1160 (5) | −0.1174 (5) | 0.095 (2) | |
H16 | 0.2929 | 0.1202 | −0.1456 | 0.114* | |
C17 | 0.4674 (9) | 0.0658 (5) | −0.1614 (5) | 0.096 (2) | |
H17 | 0.4289 | 0.0365 | −0.2198 | 0.116* | |
C18 | 0.6050 (8) | 0.0585 (5) | −0.1196 (5) | 0.084 (2) | |
H18 | 0.6604 | 0.0237 | −0.1493 | 0.101* | |
C19 | 0.6626 (6) | 0.1027 (4) | −0.0334 (4) | 0.0722 (17) | |
H19 | 0.7567 | 0.0977 | −0.0053 | 0.087* | |
O1 | 0.4898 (4) | 0.1658 (3) | 0.2411 (3) | 0.0703 (12) | |
O2 | 0.6793 (4) | 0.1837 (3) | 0.3602 (2) | 0.0600 (11) | |
C21 | 0.5603 (6) | 0.1571 (4) | 0.3251 (4) | 0.0514 (13) | |
C22 | 0.4950 (6) | 0.1014 (4) | 0.3951 (4) | 0.0728 (18) | |
F1A | 0.5424 (9) | 0.1226 (6) | 0.4868 (5) | 0.0676 (14)* | 0.506 (4) |
F2A | 0.4905 (12) | 0.0161 (4) | 0.3728 (6) | 0.0676 (14)* | 0.506 (4) |
F3A | 0.3521 (6) | 0.1280 (6) | 0.3736 (6) | 0.0676 (14)* | 0.506 (4) |
F1B | 0.5099 (14) | 0.1389 (9) | 0.4797 (7) | 0.082 (3)* | 0.314 (10) |
F2B | 0.5660 (15) | 0.0222 (7) | 0.4078 (10) | 0.082 (3)* | 0.314 (10) |
F3B | 0.3731 (11) | 0.0770 (12) | 0.3692 (9) | 0.082 (3)* | 0.314 (10) |
F1C | 0.5788 (18) | 0.0854 (17) | 0.4815 (10) | 0.084 (6)* | 0.179 (10) |
F2C | 0.429 (3) | 0.0325 (13) | 0.3542 (13) | 0.084 (6)* | 0.179 (10) |
F3C | 0.3884 (19) | 0.1373 (13) | 0.4144 (18) | 0.084 (6)* | 0.179 (10) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.057 (3) | 0.093 (3) | 0.036 (2) | −0.020 (3) | 0.015 (2) | 0.000 (2) |
N2 | 0.048 (3) | 0.077 (3) | 0.032 (2) | −0.009 (2) | 0.0078 (19) | 0.008 (2) |
N3 | 0.066 (3) | 0.081 (3) | 0.037 (2) | −0.020 (3) | 0.016 (2) | 0.003 (2) |
C1 | 0.052 (3) | 0.066 (3) | 0.034 (3) | −0.005 (3) | 0.011 (2) | 0.005 (2) |
C2 | 0.048 (3) | 0.071 (4) | 0.040 (3) | −0.006 (3) | 0.015 (2) | −0.003 (3) |
C3 | 0.072 (4) | 0.074 (4) | 0.047 (3) | 0.009 (3) | 0.002 (3) | −0.004 (3) |
C4 | 0.121 (6) | 0.068 (5) | 0.076 (5) | 0.005 (4) | −0.007 (4) | −0.005 (4) |
C5 | 0.109 (6) | 0.083 (5) | 0.088 (5) | −0.015 (4) | −0.015 (4) | −0.020 (4) |
C6 | 0.076 (4) | 0.110 (6) | 0.049 (3) | −0.005 (4) | −0.009 (3) | −0.013 (4) |
C7 | 0.066 (4) | 0.086 (4) | 0.043 (3) | −0.004 (3) | 0.006 (3) | −0.001 (3) |
C8 | 0.053 (3) | 0.053 (3) | 0.034 (3) | −0.005 (3) | 0.016 (2) | −0.003 (2) |
C9 | 0.070 (4) | 0.069 (4) | 0.050 (3) | −0.002 (3) | 0.022 (3) | 0.004 (3) |
C10 | 0.080 (5) | 0.088 (5) | 0.088 (5) | −0.018 (4) | 0.047 (4) | 0.003 (4) |
C11 | 0.058 (4) | 0.117 (6) | 0.098 (5) | −0.012 (4) | 0.032 (4) | −0.022 (5) |
C12 | 0.056 (4) | 0.102 (6) | 0.071 (4) | 0.014 (4) | 0.009 (3) | −0.007 (4) |
C13 | 0.059 (4) | 0.069 (4) | 0.056 (3) | 0.007 (3) | 0.014 (3) | 0.006 (3) |
C14 | 0.055 (3) | 0.069 (4) | 0.040 (3) | −0.015 (3) | 0.010 (2) | −0.001 (3) |
C15 | 0.052 (3) | 0.096 (5) | 0.063 (4) | −0.012 (3) | 0.015 (3) | −0.018 (3) |
C16 | 0.066 (4) | 0.131 (7) | 0.080 (5) | −0.026 (4) | 0.005 (4) | −0.029 (5) |
C17 | 0.102 (6) | 0.117 (6) | 0.069 (5) | −0.027 (5) | 0.018 (4) | −0.036 (4) |
C18 | 0.104 (6) | 0.088 (5) | 0.065 (4) | 0.001 (4) | 0.030 (4) | −0.020 (4) |
C19 | 0.063 (4) | 0.086 (5) | 0.068 (4) | 0.006 (3) | 0.016 (3) | −0.005 (4) |
O1 | 0.053 (2) | 0.112 (3) | 0.045 (2) | −0.008 (2) | 0.0091 (18) | 0.003 (2) |
O2 | 0.052 (2) | 0.090 (3) | 0.038 (2) | −0.018 (2) | 0.0094 (17) | 0.0027 (18) |
C21 | 0.056 (3) | 0.067 (4) | 0.034 (3) | −0.003 (3) | 0.017 (3) | 0.003 (3) |
C22 | 0.074 (4) | 0.093 (5) | 0.050 (3) | −0.013 (4) | 0.012 (3) | −0.014 (3) |
Geometric parameters (Å, º) top
N1—C1 | 1.329 (6) | C11—H11 | 0.9300 |
N1—C14 | 1.430 (6) | C12—C13 | 1.393 (8) |
N1—H1 | 0.8600 | C12—H12 | 0.9300 |
N2—C1 | 1.346 (6) | C13—H13 | 0.9300 |
N2—C8 | 1.420 (6) | C14—C15 | 1.372 (7) |
N2—H2 | 0.8600 | C14—C19 | 1.372 (8) |
N3—C1 | 1.334 (6) | C15—C16 | 1.382 (8) |
N3—C2 | 1.411 (6) | C15—H15 | 0.9300 |
N3—H3 | 0.8600 | C16—C17 | 1.354 (9) |
C2—C3 | 1.370 (8) | C16—H16 | 0.9300 |
C2—C7 | 1.386 (7) | C17—C18 | 1.362 (9) |
C3—C4 | 1.365 (8) | C17—H17 | 0.9300 |
C3—H3A | 0.9300 | C18—C19 | 1.381 (8) |
C4—C5 | 1.370 (9) | C18—H18 | 0.9300 |
C4—H4 | 0.9300 | C19—H19 | 0.9300 |
C5—C6 | 1.358 (10) | O1—C21 | 1.231 (6) |
C5—H5 | 0.9300 | O2—C21 | 1.237 (6) |
C6—C7 | 1.377 (8) | C21—C22 | 1.552 (8) |
C6—H6 | 0.9300 | C22—F3B | 1.239 (8) |
C7—H7 | 0.9300 | C22—F3C | 1.279 (10) |
C8—C9 | 1.371 (7) | C22—F2C | 1.281 (10) |
C8—C13 | 1.381 (7) | C22—F1B | 1.295 (9) |
C9—C10 | 1.383 (8) | C22—F1A | 1.306 (8) |
C9—H9 | 0.9300 | C22—F2A | 1.310 (7) |
C10—C11 | 1.362 (9) | C22—F1C | 1.323 (10) |
C10—H10 | 0.9300 | C22—F2B | 1.368 (9) |
C11—C12 | 1.348 (9) | C22—F3A | 1.442 (7) |
| | | |
C1—N1—C14 | 127.4 (4) | C16—C17—C18 | 119.6 (7) |
C1—N1—H1 | 116.3 | C16—C17—H17 | 120.2 |
C14—N1—H1 | 116.3 | C18—C17—H17 | 120.2 |
C1—N2—C8 | 125.7 (4) | C17—C18—C19 | 120.3 (6) |
C1—N2—H2 | 117.2 | C17—C18—H18 | 119.9 |
C8—N2—H2 | 117.2 | C19—C18—H18 | 119.9 |
C1—N3—C2 | 126.5 (4) | C14—C19—C18 | 120.1 (6) |
C1—N3—H3 | 116.8 | C14—C19—H19 | 120.0 |
C2—N3—H3 | 116.8 | C18—C19—H19 | 120.0 |
N1—C1—N3 | 117.5 (4) | O1—C21—O2 | 128.5 (5) |
N1—C1—N2 | 119.2 (4) | O1—C21—C22 | 116.1 (5) |
N3—C1—N2 | 123.3 (5) | O2—C21—C22 | 115.3 (4) |
C3—C2—C7 | 120.0 (5) | F3B—C22—F3C | 51.5 (11) |
C3—C2—N3 | 121.9 (5) | F3B—C22—F2C | 43.0 (11) |
C7—C2—N3 | 117.9 (5) | F3C—C22—F2C | 93.9 (14) |
C4—C3—C2 | 119.7 (5) | F3B—C22—F1B | 106.6 (10) |
C4—C3—H3A | 120.1 | F3C—C22—F1B | 62.4 (13) |
C2—C3—H3A | 120.1 | F2C—C22—F1B | 134.0 (12) |
C3—C4—C5 | 120.7 (7) | F3B—C22—F1A | 117.3 (8) |
C3—C4—H4 | 119.7 | F3C—C22—F1A | 78.9 (12) |
C5—C4—H4 | 119.7 | F2C—C22—F1A | 131.7 (10) |
C6—C5—C4 | 119.8 (7) | F1B—C22—F1A | 17.6 (8) |
C6—C5—H5 | 120.1 | F3B—C22—F2A | 70.6 (8) |
C4—C5—H5 | 120.1 | F3C—C22—F2A | 118.5 (11) |
C5—C6—C7 | 120.6 (6) | F2C—C22—F2A | 29.2 (12) |
C5—C6—H6 | 119.7 | F1B—C22—F2A | 129.2 (8) |
C7—C6—H6 | 119.7 | F1A—C22—F2A | 117.2 (6) |
C6—C7—C2 | 119.1 (6) | F3B—C22—F1C | 125.2 (11) |
C6—C7—H7 | 120.4 | F3C—C22—F1C | 104.6 (13) |
C2—C7—H7 | 120.4 | F2C—C22—F1C | 114.3 (14) |
C9—C8—C13 | 119.8 (5) | F1B—C22—F1C | 47.4 (12) |
C9—C8—N2 | 118.6 (5) | F1A—C22—F1C | 29.9 (11) |
C13—C8—N2 | 121.5 (5) | F2A—C22—F1C | 91.3 (11) |
C8—C9—C10 | 120.5 (6) | F3B—C22—F2B | 103.0 (9) |
C8—C9—H9 | 119.8 | F3C—C22—F2B | 140.0 (11) |
C10—C9—H9 | 119.8 | F2C—C22—F2B | 63.8 (13) |
C11—C10—C9 | 119.3 (6) | F1B—C22—F2B | 108.3 (9) |
C11—C10—H10 | 120.3 | F1A—C22—F2B | 91.7 (7) |
C9—C10—H10 | 120.3 | F2A—C22—F2B | 34.7 (5) |
C12—C11—C10 | 120.8 (6) | F1C—C22—F2B | 62.1 (12) |
C12—C11—H11 | 119.6 | F3B—C22—F3A | 33.5 (7) |
C10—C11—H11 | 119.6 | F3C—C22—F3A | 25.3 (11) |
C11—C12—C13 | 120.8 (6) | F2C—C22—F3A | 75.6 (13) |
C11—C12—H12 | 119.6 | F1B—C22—F3A | 87.8 (8) |
C13—C12—H12 | 119.6 | F1A—C22—F3A | 104.1 (6) |
C8—C13—C12 | 118.7 (6) | F2A—C22—F3A | 104.0 (6) |
C8—C13—H13 | 120.7 | F1C—C22—F3A | 128.1 (11) |
C12—C13—H13 | 120.7 | F2B—C22—F3A | 136.1 (7) |
C15—C14—C19 | 119.5 (5) | F3B—C22—C21 | 120.3 (7) |
C15—C14—N1 | 117.9 (5) | F3C—C22—C21 | 114.2 (9) |
C19—C14—N1 | 122.5 (5) | F2C—C22—C21 | 113.2 (9) |
C14—C15—C16 | 119.5 (6) | F1B—C22—C21 | 112.5 (7) |
C14—C15—H15 | 120.3 | F1A—C22—C21 | 113.2 (6) |
C16—C15—H15 | 120.3 | F2A—C22—C21 | 111.3 (5) |
C17—C16—C15 | 121.0 (7) | F1C—C22—C21 | 114.5 (8) |
C17—C16—H16 | 119.5 | F2B—C22—C21 | 105.2 (6) |
C15—C16—H16 | 119.5 | F3A—C22—C21 | 105.4 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.86 | 1.90 | 2.756 (5) | 173 |
N2—H2···O2i | 0.86 | 1.99 | 2.833 (5) | 165 |
N3—H3···O2 | 0.86 | 2.00 | 2.806 (5) | 156 |
Symmetry code: (i) x, −y+1/2, z−1/2. |
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