(E)-N′-(4-Fluoro­benzyl­idene)isonicotinohydrazide monohydrate

In the title mol­ecule, C₁₃H₁₀FN₃O·H₂O, the hydrazone group adopts a trans configuration with respect to the C=N double bond. In the crystal structure, a two-dimensional network is formed via inter­molecular O—H...O, N—H...O and O—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.037
• wR factor = 0.094
• Data-to-parameter ratio = 8.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

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           27.03
           From the CIF: _reflns_number_total               1562
           Count of symmetry unique reflns         1609
           Completeness (_total/calc)             97.08%
           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
   0 ALERT level B = Potentially serious problem
   2 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 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

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

(E)—N'-(4-Fluorobenzylidene)isonicotinohydrazide monohydrate

Crystal data

C13H10FN3O·H2O	F(000) = 544
Mr = 261.26	Dx = 1.397 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2342 reflections
a = 6.469 (2) Å	θ = 3.5–27.4°
b = 7.021 (2) Å	µ = 0.11 mm^−1
c = 27.351 (9) Å	T = 292 K
V = 1242.3 (7) Å^3	Block, colourless
Z = 4	0.30 × 0.30 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1562 independent reflections
Radiation source: fine-focus sealed tube	1163 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 27.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→8
Tmin = 0.969, Tmax = 0.979	k = −8→8
5749 measured reflections	l = −31→34

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0531P)^2] where P = (Fo^2 + 2Fc^2)/3
1562 reflections	(Δ/σ)max < 0.001
184 parameters	Δρmax = 0.16 e Å^−3
3 restraints	Δρmin = −0.13 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	0.7718 (3)	0.3530 (2)	0.62537 (5)	0.0808 (5)
O1	0.6807 (3)	0.7594 (3)	0.32965 (6)	0.0641 (5)
N1	0.1360 (3)	0.8091 (3)	0.20047 (8)	0.0581 (6)
N2	0.3955 (3)	0.6675 (3)	0.37156 (7)	0.0486 (5)
N3	0.5112 (3)	0.6270 (3)	0.41284 (7)	0.0480 (5)
C1	0.3625 (3)	0.7525 (3)	0.28638 (8)	0.0436 (5)
C2	0.1573 (3)	0.8093 (3)	0.28805 (8)	0.0474 (6)
H2A	0.0910	0.8284	0.3178	0.057*
C3	0.0536 (4)	0.8368 (4)	0.24437 (9)	0.0546 (6)
H3A	−0.0831	0.8775	0.2459	0.066*
C4	0.3320 (4)	0.7530 (4)	0.19936 (9)	0.0582 (7)
H4A	0.3930	0.7323	0.1690	0.070*
C5	0.4505 (4)	0.7237 (4)	0.24083 (9)	0.0524 (6)
H5	0.5876	0.6851	0.2381	0.063*
C6	0.4950 (3)	0.7271 (3)	0.33097 (8)	0.0452 (5)
C7	0.5095 (4)	0.5356 (3)	0.49697 (8)	0.0440 (5)
C8	0.7113 (3)	0.4682 (3)	0.49771 (9)	0.0499 (6)
H8A	0.7874	0.4638	0.4689	0.060*
C9	0.8001 (4)	0.4076 (3)	0.54117 (9)	0.0550 (7)
H9A	0.9354	0.3630	0.5419	0.066*
C10	0.6836 (4)	0.4150 (3)	0.58292 (9)	0.0546 (7)
C11	0.4858 (4)	0.4796 (4)	0.58405 (9)	0.0573 (7)
H11A	0.4116	0.4829	0.6132	0.069*
C12	0.3978 (4)	0.5406 (4)	0.54054 (9)	0.0513 (6)
H12A	0.2625	0.5853	0.5404	0.062*
C13	0.4081 (4)	0.5931 (3)	0.45136 (8)	0.0474 (6)
H13A	0.2649	0.6049	0.4506	0.057*
O1W	0.0125 (3)	0.0280 (3)	0.11714 (7)	0.0546 (5)
H1N	0.258 (4)	0.642 (3)	0.3714 (8)	0.050 (7)*
H1WB	0.118 (3)	0.096 (4)	0.1164 (11)	0.109 (14)*
H1WA	0.028 (4)	−0.053 (3)	0.1397 (7)	0.065 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0906 (13)	0.0924 (11)	0.0594 (10)	0.0069 (10)	−0.0207 (9)	0.0150 (8)
O1	0.0363 (9)	0.0913 (14)	0.0648 (12)	−0.0041 (11)	−0.0040 (8)	0.0159 (10)
N1	0.0522 (13)	0.0728 (14)	0.0491 (13)	−0.0015 (11)	−0.0059 (10)	0.0081 (11)
N2	0.0353 (11)	0.0645 (13)	0.0461 (12)	−0.0009 (10)	−0.0077 (8)	0.0062 (10)
N3	0.0422 (11)	0.0570 (11)	0.0449 (11)	0.0003 (10)	−0.0080 (9)	0.0032 (10)
C1	0.0428 (13)	0.0433 (12)	0.0448 (14)	0.0012 (11)	−0.0015 (10)	0.0015 (10)
C2	0.0416 (13)	0.0569 (14)	0.0438 (14)	0.0032 (12)	0.0032 (10)	0.0051 (11)
C3	0.0396 (13)	0.0645 (15)	0.0597 (16)	0.0016 (12)	−0.0049 (12)	0.0109 (14)
C4	0.0589 (16)	0.0739 (17)	0.0419 (14)	0.0014 (16)	0.0047 (12)	−0.0018 (13)
C5	0.0442 (14)	0.0587 (14)	0.0543 (15)	0.0049 (12)	0.0045 (11)	−0.0001 (12)
C6	0.0387 (13)	0.0492 (13)	0.0476 (14)	0.0037 (12)	−0.0025 (11)	−0.0005 (11)
C7	0.0436 (12)	0.0433 (11)	0.0450 (13)	−0.0014 (11)	−0.0040 (11)	−0.0021 (10)
C8	0.0480 (14)	0.0542 (14)	0.0474 (14)	0.0027 (12)	0.0008 (11)	−0.0038 (11)
C9	0.0466 (15)	0.0526 (14)	0.0657 (17)	0.0054 (12)	−0.0097 (13)	−0.0026 (12)
C10	0.0640 (17)	0.0550 (14)	0.0448 (14)	−0.0031 (13)	−0.0159 (13)	0.0034 (12)
C11	0.0608 (16)	0.0660 (16)	0.0451 (14)	−0.0024 (15)	0.0033 (13)	0.0008 (12)
C12	0.0424 (13)	0.0597 (13)	0.0519 (14)	0.0000 (12)	−0.0032 (11)	−0.0031 (12)
C13	0.0383 (13)	0.0557 (14)	0.0480 (14)	−0.0009 (11)	−0.0076 (11)	−0.0010 (12)
O1W	0.0413 (10)	0.0704 (12)	0.0521 (11)	−0.0019 (10)	−0.0059 (8)	0.0077 (9)

Geometric parameters (Å, º)

F1—C10	1.365 (3)	C5—H5	0.9300
O1—C6	1.223 (3)	C7—C8	1.389 (3)
N1—C4	1.328 (3)	C7—C12	1.394 (3)
N1—C3	1.328 (3)	C7—C13	1.466 (3)
N2—C6	1.350 (3)	C8—C9	1.387 (3)
N2—N3	1.384 (3)	C8—H8A	0.9300
N2—H1N	0.91 (2)	C9—C10	1.369 (3)
N3—C13	1.270 (3)	C9—H9A	0.9300
C1—C5	1.385 (3)	C10—C11	1.358 (3)
C1—C2	1.387 (3)	C11—C12	1.387 (3)
C1—C6	1.501 (3)	C11—H11A	0.9300
C2—C3	1.384 (3)	C12—H12A	0.9300
C2—H2A	0.9300	C13—H13A	0.9300
C3—H3A	0.9300	O1W—H1WB	0.834 (10)
C4—C5	1.384 (3)	O1W—H1WA	0.844 (10)
C4—H4A	0.9300
C4—N1—C3	116.6 (2)	C8—C7—C12	118.9 (2)
C6—N2—N3	118.50 (19)	C8—C7—C13	121.8 (2)
C6—N2—H1N	121.6 (14)	C12—C7—C13	119.2 (2)
N3—N2—H1N	119.6 (14)	C9—C8—C7	120.4 (2)
C13—N3—N2	115.57 (19)	C9—C8—H8A	119.8
C5—C1—C2	117.7 (2)	C7—C8—H8A	119.8
C5—C1—C6	118.6 (2)	C10—C9—C8	118.4 (2)
C2—C1—C6	123.6 (2)	C10—C9—H9A	120.8
C3—C2—C1	118.4 (2)	C8—C9—H9A	120.8
C3—C2—H2A	120.8	C11—C10—F1	118.8 (2)
C1—C2—H2A	120.8	C11—C10—C9	123.4 (2)
N1—C3—C2	124.4 (2)	F1—C10—C9	117.9 (2)
N1—C3—H3A	117.8	C10—C11—C12	118.1 (2)
C2—C3—H3A	117.8	C10—C11—H11A	121.0
N1—C4—C5	123.7 (2)	C12—C11—H11A	121.0
N1—C4—H4A	118.2	C11—C12—C7	120.9 (2)
C5—C4—H4A	118.2	C11—C12—H12A	119.6
C4—C5—C1	119.2 (2)	C7—C12—H12A	119.6
C4—C5—H5	120.4	N3—C13—C7	121.5 (2)
C1—C5—H5	120.4	N3—C13—H13A	119.2
O1—C6—N2	123.4 (2)	C7—C13—H13A	119.2
O1—C6—C1	121.0 (2)	H1WB—O1W—H1WA	108.1 (19)
N2—C6—C1	115.66 (19)
C6—N2—N3—C13	172.2 (2)	C2—C1—C6—N2	32.4 (3)
C5—C1—C2—C3	−1.0 (3)	C12—C7—C8—C9	−0.2 (4)
C6—C1—C2—C3	176.9 (2)	C13—C7—C8—C9	−177.3 (2)
C4—N1—C3—C2	−0.7 (4)	C7—C8—C9—C10	0.3 (4)
C1—C2—C3—N1	1.3 (4)	C8—C9—C10—C11	−0.4 (4)
C3—N1—C4—C5	−0.2 (4)	C8—C9—C10—F1	179.3 (2)
N1—C4—C5—C1	0.4 (4)	F1—C10—C11—C12	−179.4 (2)
C2—C1—C5—C4	0.2 (4)	C9—C10—C11—C12	0.2 (4)
C6—C1—C5—C4	−177.8 (2)	C10—C11—C12—C7	0.0 (4)
N3—N2—C6—O1	−5.0 (4)	C8—C7—C12—C11	0.0 (4)
N3—N2—C6—C1	175.06 (19)	C13—C7—C12—C11	177.3 (2)
C5—C1—C6—O1	30.3 (3)	N2—N3—C13—C7	175.8 (2)
C2—C1—C6—O1	−147.6 (3)	C8—C7—C13—N3	−16.9 (3)
C5—C1—C6—N2	−149.7 (2)	C12—C7—C13—N3	165.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N···O1W^i	0.91 (2)	1.95 (2)	2.832 (3)	164 (2)
O1W—H1WB···O1^ii	0.83 (1)	2.28 (2)	2.949 (2)	138 (3)
O1W—H1WB···N3^ii	0.83 (1)	2.54 (2)	3.264 (3)	146 (3)
O1W—H1WA···N1^iii	0.84 (1)	2.05 (1)	2.863 (3)	162 (2)

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1, y−1/2, −z+1/2; (iii) x, y−1, z.