2′-(2-Fluoro­benzyl­idene)-2-hydroxy­benzohydrazide

The title compound, C₁₄H₁₁FN₂O₂, was synthesized by the reaction of 2-hydroxy­benzoyl­hydrazine with 2-fluoro­benz­aldehyde in ethanol. The mol­ecule is planar and an intramolecular N—H...O hydrogen bond is observed. In the crystal packing, symmetry-related mol­ecules form O—H...O hydrogen-bonded chains along the [201] direction.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.054
• wR factor = 0.142
• Data-to-parameter ratio = 10.0

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.117
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.12
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 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
   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: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2'-(2-Fluorobenzylidene)-2-hydroxybenzohydrazide

Crystal data

C14H11FN2O2	F(000) = 536
Mr = 258.25	Dx = 1.418 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1820 reflections
a = 4.9184 (8) Å	θ = 5.2–51.7°
b = 23.655 (4) Å	µ = 0.11 mm^−1
c = 10.6092 (17) Å	T = 298 K
β = 101.556 (3)°	Block, colourless
V = 1209.3 (3) Å^3	0.49 × 0.35 × 0.11 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer	2164 independent reflections
Radiation source: fine-focus sealed tube	1639 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.117
φ and ω scans	θmax = 25.2°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −5→5
Tmin = 0.949, Tmax = 0.988	k = −28→25
6145 measured reflections	l = −12→12

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.142	All H-atom parameters refined
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0729P)^2] where P = (Fo^2 + 2Fc^2)/3
2164 reflections	(Δ/σ)max < 0.001
216 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.23 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
O1	0.6833 (3)	0.27703 (6)	0.54273 (12)	0.0560 (4)
O2	1.2128 (3)	0.25805 (6)	0.89889 (13)	0.0546 (4)
N1	0.7708 (3)	0.22816 (6)	0.72823 (16)	0.0471 (4)
N2	0.5610 (3)	0.19035 (6)	0.68623 (14)	0.0444 (4)
F1	0.5519 (3)	0.05635 (6)	0.91684 (12)	0.0779 (5)
C1	0.8221 (4)	0.27020 (7)	0.65177 (17)	0.0415 (5)
C2	1.0573 (4)	0.30864 (7)	0.70406 (16)	0.0392 (4)
C3	1.2451 (4)	0.30180 (7)	0.82047 (17)	0.0398 (5)
C4	1.4623 (4)	0.33952 (8)	0.8553 (2)	0.0497 (5)
C5	1.4925 (5)	0.38435 (9)	0.7774 (2)	0.0550 (6)
C6	1.3060 (5)	0.39294 (9)	0.6642 (2)	0.0579 (6)
C7	1.0925 (4)	0.35514 (8)	0.62825 (19)	0.0515 (5)
C8	0.5416 (4)	0.15094 (8)	0.76425 (19)	0.0493 (5)
C9	0.3324 (4)	0.10676 (8)	0.73338 (17)	0.0445 (5)
C10	0.1188 (4)	0.10818 (9)	0.6263 (2)	0.0517 (5)
C11	−0.0719 (5)	0.06531 (9)	0.6017 (2)	0.0636 (6)
C12	−0.0569 (5)	0.01991 (10)	0.6845 (2)	0.0660 (7)
C13	0.1519 (5)	0.01713 (10)	0.7919 (2)	0.0608 (6)
C14	0.3410 (4)	0.06011 (8)	0.81343 (19)	0.0504 (5)
H1	0.874 (5)	0.2244 (8)	0.806 (2)	0.058 (6)*
H2	1.363 (6)	0.2514 (11)	0.960 (3)	0.090 (9)*
H4	1.590 (4)	0.3328 (10)	0.933 (2)	0.070 (6)*
H5	1.642 (5)	0.4067 (10)	0.799 (2)	0.067 (7)*
H6	1.324 (4)	0.4254 (10)	0.608 (2)	0.072 (7)*
H7	0.958 (4)	0.3581 (9)	0.550 (2)	0.066 (6)*
H8	0.673 (4)	0.1495 (9)	0.847 (2)	0.068 (6)*
H10	0.108 (4)	0.1366 (9)	0.566 (2)	0.062 (6)*
H11	−0.233 (5)	0.0680 (11)	0.535 (3)	0.084 (8)*
H12	−0.193 (5)	−0.0095 (12)	0.677 (2)	0.080 (7)*
H13	0.171 (5)	−0.0112 (11)	0.842 (2)	0.076 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0607 (9)	0.0558 (9)	0.0394 (8)	−0.0073 (7)	−0.0188 (6)	0.0054 (6)
O2	0.0539 (9)	0.0539 (8)	0.0442 (8)	−0.0110 (7)	−0.0181 (7)	0.0157 (6)
N1	0.0509 (10)	0.0427 (9)	0.0383 (9)	−0.0076 (7)	−0.0134 (7)	0.0005 (7)
N2	0.0486 (9)	0.0400 (9)	0.0382 (8)	−0.0034 (7)	−0.0067 (7)	−0.0051 (7)
F1	0.0934 (10)	0.0770 (9)	0.0527 (8)	−0.0058 (7)	−0.0107 (7)	0.0201 (6)
C1	0.0448 (10)	0.0387 (10)	0.0354 (9)	0.0041 (8)	−0.0053 (8)	−0.0012 (8)
C2	0.0434 (10)	0.0345 (9)	0.0356 (9)	0.0045 (7)	−0.0022 (8)	−0.0020 (7)
C3	0.0421 (10)	0.0377 (10)	0.0358 (9)	0.0012 (8)	−0.0012 (8)	−0.0011 (8)
C4	0.0496 (12)	0.0505 (12)	0.0426 (11)	−0.0062 (9)	−0.0063 (9)	−0.0035 (9)
C5	0.0606 (14)	0.0479 (12)	0.0536 (12)	−0.0152 (10)	0.0041 (10)	−0.0056 (10)
C6	0.0761 (15)	0.0450 (12)	0.0500 (12)	−0.0105 (11)	0.0061 (11)	0.0042 (10)
C7	0.0614 (13)	0.0460 (12)	0.0408 (11)	−0.0017 (9)	−0.0054 (9)	0.0035 (9)
C8	0.0595 (12)	0.0449 (11)	0.0369 (10)	−0.0038 (9)	−0.0060 (9)	−0.0010 (9)
C9	0.0549 (12)	0.0370 (10)	0.0394 (10)	0.0021 (8)	0.0045 (9)	−0.0033 (8)
C10	0.0577 (12)	0.0420 (11)	0.0504 (12)	0.0005 (9)	−0.0012 (10)	0.0024 (10)
C11	0.0629 (14)	0.0551 (13)	0.0643 (14)	−0.0096 (11)	−0.0079 (12)	0.0017 (11)
C12	0.0722 (15)	0.0455 (13)	0.0782 (16)	−0.0109 (11)	0.0097 (13)	−0.0018 (11)
C13	0.0787 (16)	0.0429 (13)	0.0619 (14)	0.0012 (11)	0.0165 (12)	0.0093 (11)
C14	0.0594 (12)	0.0492 (12)	0.0406 (10)	0.0028 (10)	0.0049 (9)	0.0029 (9)

Geometric parameters (Å, º)

O1—C1	1.230 (2)	C6—C7	1.374 (3)
O2—C3	1.357 (2)	C6—H6	0.99 (2)
O2—H2	0.89 (3)	C7—H7	0.96 (2)
N1—C1	1.339 (2)	C8—C9	1.457 (3)
N1—N2	1.371 (2)	C8—H8	0.98 (2)
N1—H1	0.88 (2)	C9—C10	1.385 (3)
N2—C8	1.263 (2)	C9—C14	1.388 (3)
F1—C14	1.353 (2)	C10—C11	1.370 (3)
C1—C2	1.488 (2)	C10—H10	0.92 (2)
C2—C7	1.394 (3)	C11—C12	1.380 (3)
C2—C3	1.396 (2)	C11—H11	0.96 (3)
C3—C4	1.384 (3)	C12—C13	1.374 (3)
C4—C5	1.371 (3)	C12—H12	0.96 (3)
C4—H4	0.95 (2)	C13—C14	1.366 (3)
C5—C6	1.372 (3)	C13—H13	0.85 (3)
C5—H5	0.90 (2)
C3—O2—H2	113.2 (17)	C6—C7—H7	123.5 (13)
C1—N1—N2	120.58 (15)	C2—C7—H7	114.5 (13)
C1—N1—H1	119.7 (14)	N2—C8—C9	121.65 (17)
N2—N1—H1	119.7 (14)	N2—C8—H8	119.3 (13)
C8—N2—N1	114.79 (16)	C9—C8—H8	119.1 (13)
O1—C1—N1	122.05 (16)	C10—C9—C14	116.52 (18)
O1—C1—C2	120.90 (17)	C10—C9—C8	123.54 (17)
N1—C1—C2	117.05 (15)	C14—C9—C8	119.95 (17)
C7—C2—C3	117.74 (16)	C11—C10—C9	121.1 (2)
C7—C2—C1	116.37 (15)	C11—C10—H10	117.5 (13)
C3—C2—C1	125.88 (16)	C9—C10—H10	121.2 (13)
O2—C3—C4	120.47 (16)	C10—C11—C12	120.5 (2)
O2—C3—C2	119.54 (15)	C10—C11—H11	121.8 (15)
C4—C3—C2	119.99 (17)	C12—C11—H11	117.2 (15)
C5—C4—C3	120.60 (19)	C13—C12—C11	120.0 (2)
C5—C4—H4	121.6 (14)	C13—C12—H12	115.6 (15)
C3—C4—H4	117.8 (14)	C11—C12—H12	124.2 (15)
C4—C5—C6	120.5 (2)	C14—C13—C12	118.3 (2)
C4—C5—H5	119.0 (15)	C14—C13—H13	120.0 (17)
C6—C5—H5	120.3 (15)	C12—C13—H13	121.6 (17)
C5—C6—C7	119.1 (2)	F1—C14—C13	118.18 (18)
C5—C6—H6	121.0 (14)	F1—C14—C9	118.21 (18)
C7—C6—H6	119.9 (13)	C13—C14—C9	123.6 (2)
C6—C7—C2	121.98 (18)
C1—N1—N2—C8	176.55 (18)	C3—C2—C7—C6	1.0 (3)
N2—N1—C1—O1	0.9 (3)	C1—C2—C7—C6	−178.29 (19)
N2—N1—C1—C2	−178.81 (15)	N1—N2—C8—C9	−178.99 (17)
O1—C1—C2—C7	6.0 (3)	N2—C8—C9—C10	−8.8 (3)
N1—C1—C2—C7	−174.36 (17)	N2—C8—C9—C14	171.22 (19)
O1—C1—C2—C3	−173.27 (18)	C14—C9—C10—C11	−0.3 (3)
N1—C1—C2—C3	6.4 (3)	C8—C9—C10—C11	179.8 (2)
C7—C2—C3—O2	177.96 (17)	C9—C10—C11—C12	0.8 (4)
C1—C2—C3—O2	−2.8 (3)	C10—C11—C12—C13	−0.7 (4)
C7—C2—C3—C4	−2.0 (3)	C11—C12—C13—C14	0.0 (4)
C1—C2—C3—C4	177.25 (17)	C12—C13—C14—F1	−177.8 (2)
O2—C3—C4—C5	−178.79 (18)	C12—C13—C14—C9	0.6 (3)
C2—C3—C4—C5	1.1 (3)	C10—C9—C14—F1	177.93 (17)
C3—C4—C5—C6	0.8 (3)	C8—C9—C14—F1	−2.1 (3)
C4—C5—C6—C7	−1.7 (3)	C10—C9—C14—C13	−0.5 (3)
C5—C6—C7—C2	0.8 (3)	C8—C9—C14—C13	179.49 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.88 (2)	1.93 (2)	2.632 (2)	136 (2)
O2—H2···O1^i	0.89 (3)	1.77 (3)	2.638 (2)	162 (3)

Symmetry code: (i) x+1, −y+1/2, z+1/2.