3-[(4-Fluoro­phenyl)­methyl­enehydrazino­carbonyl]-1H-1,2,4-triazole monohydrate

The title compound, C₁₀H₈FN₅O·H₂O, was synthesized by the reaction of (1H-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.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](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

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Computing details

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]-1H-1,2,4-triazole monohydrate

Crystal data

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) Å^3	0.20 × 0.20 × 0.10 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.189	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0903P)^2] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···N3^i	0.86	2.34	2.934 (5)	127
N5—H5···O1^i	0.86	2.11	2.913 (5)	155
N2—H2···O2	0.86	2.26	2.880 (5)	129
O2—H22···N1^ii	0.85 (1)	2.16 (2)	2.971 (5)	161 (6)
O2—H21···N4^iii	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.