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The title compound, C
10H
8FN
5O·H
2O, was synthesized by the reaction of (1
H-1,2,4-triazol-3-yl)hydrazine with 4-fluorobenzaldehyde in ethanol. The molecule is almost planar and in the crystal structure screw-related molecules are linked by N—H
O and N—H
N hydrogen bonds to form chains along the
b axis. The chains are interlinked by the water molecules
via O—H
N hydrogen bonds.
Supporting information
CCDC reference: 269411
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.007 Å
- R factor = 0.057
- wR factor = 0.189
- Data-to-parameter ratio = 12.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 38 Perc.
PLAT731_ALERT_1_B Bond Calc 0.85(5), Rep 0.850(10) ...... 5.00 su-Rat
O2 -H22 1.555 1.555
PLAT735_ALERT_1_B D-H Calc 0.85(5), Rep 0.850(10) ...... 5.00 su-Rat
O2 -H22 1.555 1.555
Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT731_ALERT_1_C Bond Calc 0.85(4), Rep 0.850(10) ...... 4.00 su-Rat
O2 -H21 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.85(4), Rep 0.850(10) ...... 4.00 su-Rat
O2 -H21 1.555 1.555
PLAT736_ALERT_1_C H...A Calc 2.15(5), Rep 2.16(2) ...... 2.50 su-Rat
H22 -N1 1.555 4.576
0 ALERT level A = In general: serious problem
3 ALERT level B = Potentially serious problem
4 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CAD-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.
3-[(4-Fluorophenyl)methylenehydrazinocarbonyl]-1
H-1,2,4-triazole
monohydrate
top
Crystal data top
C10H8FN5O·H2O | F(000) = 520 |
Mr = 251.23 | Dx = 1.449 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 21.394 (2) Å | θ = 8.4–12.5° |
b = 7.796 (2) Å | µ = 0.12 mm−1 |
c = 6.918 (2) Å | T = 295 K |
β = 93.70 (2)° | Block, colourless |
V = 1151.4 (5) Å3 | 0.20 × 0.20 × 0.10 mm |
Z = 4 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.064 |
Radiation source: fine-focus sealed tube | θmax = 25.2°, θmin = 2.8° |
Graphite monochromator | h = −25→25 |
ω/2θ scans | k = −9→1 |
2623 measured reflections | l = 0→8 |
2072 independent reflections | 3 standard reflections every 60 min |
786 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.189 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0903P)2] where P = (Fo2 + 2Fc2)/3 |
2072 reflections | (Δ/σ)max = 0.006 |
171 parameters | Δρmax = 0.29 e Å−3 |
3 restraints | Δρmin = −0.26 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 | |
F1 | 0.95154 (15) | 1.2356 (5) | 0.8822 (6) | 0.1019 (14) | |
O1 | 0.60776 (13) | 0.8066 (4) | 0.3476 (5) | 0.0479 (9) | |
H21 | 0.694 (2) | 0.326 (5) | 0.792 (10) | 0.12 (3)* | |
H22 | 0.715 (3) | 0.483 (6) | 0.862 (8) | 0.14 (3)* | |
O2 | 0.72091 (17) | 0.4040 (5) | 0.7805 (6) | 0.0559 (10) | |
N1 | 0.72591 (16) | 0.7843 (4) | 0.5281 (5) | 0.0376 (10) | |
N2 | 0.68875 (15) | 0.6451 (5) | 0.4747 (5) | 0.0376 (10) | |
H2 | 0.7027 | 0.5429 | 0.4961 | 0.045* | |
N3 | 0.53760 (18) | 0.5053 (5) | 0.2974 (6) | 0.0452 (10) | |
N4 | 0.62348 (17) | 0.3459 (5) | 0.3700 (6) | 0.0459 (11) | |
N5 | 0.52421 (17) | 0.3365 (5) | 0.2802 (6) | 0.0475 (11) | |
H5 | 0.4879 | 0.2947 | 0.2462 | 0.057* | |
C1 | 0.9093 (2) | 1.1180 (8) | 0.8123 (8) | 0.0631 (17) | |
C2 | 0.9296 (3) | 0.9550 (9) | 0.7828 (9) | 0.0736 (19) | |
H2A | 0.9715 | 0.9256 | 0.8089 | 0.088* | |
C3 | 0.8865 (2) | 0.8346 (8) | 0.7133 (8) | 0.0614 (15) | |
H3 | 0.8996 | 0.7224 | 0.6945 | 0.074* | |
C4 | 0.8248 (2) | 0.8767 (6) | 0.6713 (7) | 0.0425 (12) | |
C5 | 0.8058 (2) | 1.0450 (6) | 0.7086 (7) | 0.0493 (13) | |
H5A | 0.7640 | 1.0758 | 0.6852 | 0.059* | |
C6 | 0.8485 (2) | 1.1645 (7) | 0.7797 (7) | 0.0562 (14) | |
H6 | 0.8359 | 1.2760 | 0.8052 | 0.067* | |
C7 | 0.7804 (2) | 0.7471 (6) | 0.6035 (6) | 0.0419 (12) | |
H7 | 0.7918 | 0.6323 | 0.6151 | 0.050* | |
C8 | 0.63178 (19) | 0.6675 (6) | 0.3907 (6) | 0.0342 (10) | |
C9 | 0.59735 (19) | 0.5051 (5) | 0.3517 (6) | 0.0338 (10) | |
C10 | 0.5749 (2) | 0.2456 (6) | 0.3230 (7) | 0.0465 (13) | |
H10 | 0.5764 | 0.1264 | 0.3208 | 0.056* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1 | 0.076 (2) | 0.107 (3) | 0.121 (3) | −0.045 (2) | −0.004 (2) | −0.034 (2) |
O1 | 0.0483 (19) | 0.0316 (18) | 0.063 (2) | 0.0024 (16) | 0.0002 (17) | 0.0082 (16) |
O2 | 0.059 (2) | 0.038 (2) | 0.070 (3) | −0.002 (2) | −0.0008 (18) | 0.003 (2) |
N1 | 0.040 (2) | 0.032 (2) | 0.041 (2) | −0.0035 (18) | 0.0016 (18) | −0.0013 (17) |
N2 | 0.040 (2) | 0.025 (2) | 0.047 (2) | −0.0010 (17) | 0.0028 (18) | −0.0065 (17) |
N3 | 0.048 (2) | 0.030 (2) | 0.058 (3) | −0.0037 (19) | 0.002 (2) | −0.004 (2) |
N4 | 0.047 (2) | 0.029 (2) | 0.060 (3) | 0.001 (2) | −0.001 (2) | −0.003 (2) |
N5 | 0.049 (2) | 0.030 (2) | 0.063 (3) | −0.008 (2) | 0.004 (2) | −0.006 (2) |
C1 | 0.048 (3) | 0.079 (5) | 0.062 (4) | −0.027 (3) | 0.002 (3) | −0.009 (3) |
C2 | 0.049 (3) | 0.087 (5) | 0.083 (5) | −0.004 (3) | −0.007 (3) | −0.019 (4) |
C3 | 0.055 (3) | 0.066 (4) | 0.062 (4) | 0.009 (3) | −0.001 (3) | −0.012 (3) |
C4 | 0.045 (3) | 0.043 (3) | 0.040 (3) | 0.000 (2) | 0.004 (2) | 0.001 (2) |
C5 | 0.048 (3) | 0.048 (3) | 0.052 (3) | −0.003 (3) | 0.004 (2) | −0.001 (3) |
C6 | 0.068 (4) | 0.045 (3) | 0.056 (4) | −0.015 (3) | 0.005 (3) | −0.010 (3) |
C7 | 0.048 (3) | 0.039 (3) | 0.039 (3) | 0.000 (2) | 0.010 (2) | 0.001 (2) |
C8 | 0.035 (2) | 0.034 (3) | 0.034 (3) | 0.001 (2) | 0.003 (2) | 0.003 (2) |
C9 | 0.034 (2) | 0.032 (3) | 0.034 (3) | 0.001 (2) | −0.001 (2) | −0.001 (2) |
C10 | 0.052 (3) | 0.030 (2) | 0.056 (4) | 0.001 (3) | −0.004 (2) | −0.003 (2) |
Geometric parameters (Å, º) top
F1—C1 | 1.355 (6) | C1—C6 | 1.355 (7) |
O1—C8 | 1.229 (5) | C1—C2 | 1.363 (8) |
O2—H21 | 0.85 (1) | C2—C3 | 1.380 (7) |
O2—H22 | 0.85 (1) | C2—H2A | 0.93 |
N1—C7 | 1.279 (5) | C3—C4 | 1.373 (6) |
N1—N2 | 1.382 (4) | C3—H3 | 0.93 |
N2—C8 | 1.328 (5) | C4—C5 | 1.403 (6) |
N2—H2 | 0.86 | C4—C7 | 1.445 (6) |
N3—C9 | 1.309 (5) | C5—C6 | 1.374 (6) |
N3—N5 | 1.351 (5) | C5—H5A | 0.93 |
N4—C10 | 1.325 (5) | C6—H6 | 0.93 |
N4—C9 | 1.364 (5) | C7—H7 | 0.93 |
N5—C10 | 1.312 (5) | C8—C9 | 1.481 (6) |
N5—H5 | 0.86 | C10—H10 | 0.93 |
| | | |
H21—O2—H22 | 109 (3) | C3—C4—C7 | 120.4 (5) |
C7—N1—N2 | 115.1 (4) | C5—C4—C7 | 121.4 (4) |
C8—N2—N1 | 120.6 (4) | C6—C5—C4 | 120.4 (5) |
C8—N2—H2 | 119.7 | C6—C5—H5A | 119.8 |
N1—N2—H2 | 119.7 | C4—C5—H5A | 119.8 |
C9—N3—N5 | 102.8 (4) | C1—C6—C5 | 119.1 (5) |
C10—N4—C9 | 101.7 (4) | C1—C6—H6 | 120.4 |
C10—N5—N3 | 109.8 (4) | C5—C6—H6 | 120.4 |
C10—N5—H5 | 125.1 | N1—C7—C4 | 122.5 (4) |
N3—N5—H5 | 125.1 | N1—C7—H7 | 118.7 |
C6—C1—F1 | 119.3 (6) | C4—C7—H7 | 118.7 |
C6—C1—C2 | 122.5 (5) | O1—C8—N2 | 125.5 (4) |
F1—C1—C2 | 118.2 (5) | O1—C8—C9 | 121.0 (4) |
C1—C2—C3 | 118.2 (5) | N2—C8—C9 | 113.5 (4) |
C1—C2—H2A | 120.9 | N3—C9—N4 | 114.5 (4) |
C3—C2—H2A | 120.9 | N3—C9—C8 | 121.1 (4) |
C4—C3—C2 | 121.5 (5) | N4—C9—C8 | 124.4 (4) |
C4—C3—H3 | 119.2 | N5—C10—N4 | 111.2 (4) |
C2—C3—H3 | 119.2 | N5—C10—H10 | 124.4 |
C3—C4—C5 | 118.1 (5) | N4—C10—H10 | 124.4 |
| | | |
C7—N1—N2—C8 | −178.4 (4) | C5—C4—C7—N1 | 18.1 (7) |
C9—N3—N5—C10 | −0.1 (5) | N1—N2—C8—O1 | 2.4 (6) |
C6—C1—C2—C3 | 1.4 (9) | N1—N2—C8—C9 | −177.2 (4) |
F1—C1—C2—C3 | 179.4 (5) | N5—N3—C9—N4 | 0.2 (5) |
C1—C2—C3—C4 | 1.1 (9) | N5—N3—C9—C8 | −179.2 (4) |
C2—C3—C4—C5 | −2.7 (8) | C10—N4—C9—N3 | −0.2 (5) |
C2—C3—C4—C7 | −178.4 (5) | C10—N4—C9—C8 | 179.1 (4) |
C3—C4—C5—C6 | 2.0 (7) | O1—C8—C9—N3 | −10.2 (7) |
C7—C4—C5—C6 | 177.6 (5) | N2—C8—C9—N3 | 169.4 (4) |
F1—C1—C6—C5 | 179.9 (5) | O1—C8—C9—N4 | 170.5 (4) |
C2—C1—C6—C5 | −2.1 (9) | N2—C8—C9—N4 | −9.9 (6) |
C4—C5—C6—C1 | 0.3 (8) | N3—N5—C10—N4 | 0.0 (6) |
N2—N1—C7—C4 | −178.7 (4) | C9—N4—C10—N5 | 0.1 (5) |
C3—C4—C7—N1 | −166.4 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5···N3i | 0.86 | 2.34 | 2.934 (5) | 127 |
N5—H5···O1i | 0.86 | 2.11 | 2.913 (5) | 155 |
N2—H2···O2 | 0.86 | 2.26 | 2.880 (5) | 129 |
O2—H22···N1ii | 0.85 (1) | 2.16 (2) | 2.971 (5) | 161 (6) |
O2—H21···N4iii | 0.85 (1) | 2.11 (2) | 2.948 (5) | 169 (6) |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x, −y+3/2, z+1/2; (iii) x, −y+1/2, z+1/2. |
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