



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809006941/su2098sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536809006941/su2098Isup2.hkl |
CCDC reference: 726301
Key indicators
- Single-crystal X-ray study
- T = 297 K
- Mean
(C-C) = 0.006 Å
- Disorder in main residue
- R factor = 0.088
- wR factor = 0.240
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
Alert level C Value of measurement temperature given = 297.000 Value of melting point given = 0.000 PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6 PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C10 - C11 ... 1.39 Ang. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C11 - C12 ... 1.39 Ang. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C12 - C13 ... 1.39 Ang. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C13 - C14 ... 1.39 Ang. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT234_ALERT_4_C Large Hirshfeld Difference O1 -- C6 .. 0.11 Ang. PLAT234_ALERT_4_C Large Hirshfeld Difference C12 -- C13 .. 0.11 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 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 4 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Equimolar amounts of 2-Hydroxybenzohydrazide and 3-fluorobenzohydrazide were reacted in ethanol (10 ml) for 1 h. After allowing the resulting solution to stand in air for 10 days yellow block-shaped crystals were formed, on slow evaporation of the solvent.
Phenyl ring C9-C14 was treated as a regular hexagon, and refined as a rigid body. The F-atom was found to be disordered over two positions, F1/F1', and given occupancies of 0.5/0.5. The H-atoms at C11 and C13 were also given occupancies of 0.5/0.5. All the H-atoms were placed in calculated positions and treated as riding: O-H = 0.82 Å, N-H = 0.86 Å, C-H = 0.93 Å, with Uiso(H) = 1.5Ueq(parent O and N-atom, and = 1.2Ueq(parent C-atom).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
C14H11FN2O2 | F(000) = 536 |
Mr = 258.25 | Dx = 1.410 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 589 reflections |
a = 4.8751 (15) Å | θ = 2.3–15° |
b = 22.188 (7) Å | µ = 0.11 mm−1 |
c = 11.323 (3) Å | T = 297 K |
β = 96.717 (5)° | Block, yellow |
V = 1216.4 (6) Å3 | 0.20 × 0.10 × 0.10 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 2152 independent reflections |
Radiation source: fine-focus sealed tube | 1205 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.081 |
ϕ and ω scans | θmax = 25.1°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −5→5 |
Tmin = 0.979, Tmax = 0.989 | k = −26→26 |
8534 measured reflections | l = −13→13 |
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)] = 0.088 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.240 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.1113P)2 + 0.2945P] where P = (Fo2 + 2Fc2)/3 |
2152 reflections | (Δ/σ)max = 0.002 |
170 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
C14H11FN2O2 | V = 1216.4 (6) Å3 |
Mr = 258.25 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 4.8751 (15) Å | µ = 0.11 mm−1 |
b = 22.188 (7) Å | T = 297 K |
c = 11.323 (3) Å | 0.20 × 0.10 × 0.10 mm |
β = 96.717 (5)° |
Bruker SMART CCD area-detector diffractometer | 2152 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1205 reflections with I > 2σ(I) |
Tmin = 0.979, Tmax = 0.989 | Rint = 0.081 |
8534 measured reflections |
R[F2 > 2σ(F2)] = 0.088 | 0 restraints |
wR(F2) = 0.240 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.20 e Å−3 |
2152 reflections | Δρmin = −0.30 e Å−3 |
170 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles |
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 > 2sigma(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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
F1 | −0.2554 (15) | 0.0383 (3) | 0.4844 (5) | 0.103 (3) | 0.500 |
F1' | −0.3673 (19) | 0.0122 (3) | 0.0916 (6) | 0.136 (4) | 0.500 |
O1 | 0.8661 (7) | 0.26546 (15) | 0.1078 (3) | 0.0638 (11) | |
O2 | 0.7116 (7) | 0.27530 (14) | 0.4613 (2) | 0.0643 (11) | |
N1 | 0.5969 (8) | 0.23163 (16) | 0.2828 (3) | 0.0518 (12) | |
N2 | 0.4125 (7) | 0.19142 (17) | 0.3234 (3) | 0.0490 (12) | |
C1 | 0.9330 (8) | 0.31131 (19) | 0.3001 (4) | 0.0443 (12) | |
C2 | 1.0667 (10) | 0.3559 (2) | 0.3713 (4) | 0.0563 (16) | |
C3 | 1.2548 (11) | 0.3939 (2) | 0.3302 (4) | 0.0658 (19) | |
C4 | 1.3165 (10) | 0.3890 (2) | 0.2158 (4) | 0.0601 (17) | |
C5 | 1.1869 (9) | 0.34596 (19) | 0.1418 (4) | 0.0527 (17) | |
C6 | 0.9959 (8) | 0.30710 (19) | 0.1824 (3) | 0.0433 (14) | |
C7 | 0.7399 (9) | 0.27175 (19) | 0.3545 (4) | 0.0465 (17) | |
C8 | 0.2866 (9) | 0.1604 (2) | 0.2415 (4) | 0.0524 (17) | |
C9 | 0.0844 (6) | 0.11357 (12) | 0.2623 (3) | 0.0497 (17) | |
C10 | 0.0213 (6) | 0.09879 (13) | 0.3754 (2) | 0.0520 (16) | |
C11 | −0.1728 (7) | 0.05426 (14) | 0.3894 (3) | 0.067 (2) | |
C12 | −0.3037 (6) | 0.02449 (13) | 0.2905 (4) | 0.0750 (19) | |
C13 | −0.2406 (7) | 0.03926 (15) | 0.1774 (3) | 0.083 (2) | |
C14 | −0.0466 (7) | 0.08380 (16) | 0.1634 (2) | 0.073 (2) | |
H1N | 0.62100 | 0.23090 | 0.20870 | 0.0620* | |
H1O | 0.96210 | 0.25770 | 0.05500 | 0.0950* | |
H2 | 1.02690 | 0.36010 | 0.44930 | 0.0680* | |
H3 | 1.34130 | 0.42320 | 0.38030 | 0.0790* | |
H4 | 1.44560 | 0.41470 | 0.18810 | 0.0720* | |
H5 | 1.22770 | 0.34290 | 0.06380 | 0.0630* | |
H8 | 0.32300 | 0.16740 | 0.16390 | 0.0630* | |
H10 | 0.10890 | 0.11870 | 0.44160 | 0.0620* | |
H11 | −0.21500 | 0.04440 | 0.46510 | 0.0800* | 0.500 |
H12 | −0.43350 | −0.00530 | 0.29990 | 0.0900* | |
H13 | −0.32820 | 0.01930 | 0.11120 | 0.0990* | 0.500 |
H14 | −0.00440 | 0.09370 | 0.08770 | 0.0870* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.145 (6) | 0.094 (5) | 0.080 (4) | −0.033 (5) | 0.054 (4) | 0.006 (4) |
F1' | 0.184 (8) | 0.138 (6) | 0.075 (4) | −0.103 (6) | −0.026 (5) | −0.006 (4) |
O1 | 0.076 (2) | 0.075 (2) | 0.0473 (19) | −0.0178 (19) | 0.0363 (16) | −0.0120 (17) |
O2 | 0.081 (2) | 0.075 (2) | 0.0416 (18) | −0.0068 (18) | 0.0274 (17) | −0.0018 (15) |
N1 | 0.063 (2) | 0.056 (2) | 0.041 (2) | −0.005 (2) | 0.0255 (19) | 0.0029 (18) |
N2 | 0.051 (2) | 0.053 (2) | 0.047 (2) | 0.003 (2) | 0.0222 (18) | 0.0074 (19) |
C1 | 0.045 (2) | 0.042 (2) | 0.048 (2) | 0.011 (2) | 0.014 (2) | 0.006 (2) |
C2 | 0.074 (3) | 0.053 (3) | 0.044 (2) | 0.001 (3) | 0.016 (2) | −0.002 (2) |
C3 | 0.080 (4) | 0.053 (3) | 0.064 (3) | −0.013 (3) | 0.007 (3) | 0.000 (3) |
C4 | 0.061 (3) | 0.062 (3) | 0.059 (3) | −0.008 (3) | 0.014 (2) | 0.011 (3) |
C5 | 0.061 (3) | 0.050 (3) | 0.051 (3) | −0.002 (2) | 0.023 (2) | 0.007 (2) |
C6 | 0.047 (3) | 0.045 (2) | 0.040 (2) | 0.004 (2) | 0.014 (2) | −0.004 (2) |
C7 | 0.054 (3) | 0.048 (3) | 0.041 (3) | 0.013 (2) | 0.021 (2) | 0.001 (2) |
C8 | 0.058 (3) | 0.059 (3) | 0.042 (3) | 0.009 (3) | 0.014 (2) | 0.009 (2) |
C9 | 0.052 (3) | 0.047 (3) | 0.052 (3) | 0.009 (2) | 0.014 (2) | 0.005 (2) |
C10 | 0.061 (3) | 0.041 (2) | 0.057 (3) | 0.002 (2) | 0.019 (2) | 0.000 (2) |
C11 | 0.076 (4) | 0.049 (3) | 0.080 (4) | 0.001 (3) | 0.031 (3) | 0.006 (3) |
C12 | 0.060 (3) | 0.055 (3) | 0.111 (4) | −0.004 (3) | 0.014 (3) | 0.008 (3) |
C13 | 0.085 (4) | 0.077 (4) | 0.085 (4) | −0.017 (3) | 0.004 (3) | 0.001 (3) |
C14 | 0.078 (4) | 0.084 (4) | 0.055 (3) | −0.012 (3) | 0.003 (3) | −0.005 (3) |
F1'—C13 | 1.243 (8) | C9—C10 | 1.3908 |
F1—C11 | 1.243 (7) | C9—C14 | 1.3896 |
O1—C6 | 1.357 (5) | C10—C11 | 1.3899 |
O2—C7 | 1.236 (5) | C11—C12 | 1.3894 |
O1—H1O | 0.8200 | C12—C13 | 1.3908 |
N1—N2 | 1.383 (5) | C13—C14 | 1.3897 |
N1—C7 | 1.344 (6) | C2—H2 | 0.9300 |
N2—C8 | 1.256 (6) | C3—H3 | 0.9300 |
N1—H1N | 0.8600 | C4—H4 | 0.9300 |
C1—C7 | 1.474 (6) | C5—H5 | 0.9300 |
C1—C2 | 1.390 (6) | C8—H8 | 0.9300 |
C1—C6 | 1.405 (6) | C10—H10 | 0.9300 |
C2—C3 | 1.367 (7) | C11—H11 | 0.9300 |
C3—C4 | 1.368 (6) | C12—H12 | 0.9300 |
C4—C5 | 1.375 (6) | C13—H13 | 0.9300 |
C5—C6 | 1.386 (6) | C14—H14 | 0.9300 |
C8—C9 | 1.470 (5) | ||
C6—O1—H1O | 109.00 | C11—C12—C13 | 120.00 |
N2—N1—C7 | 122.6 (3) | C12—C13—C14 | 119.96 |
N1—N2—C8 | 112.9 (3) | F1'—C13—C12 | 117.6 (5) |
C7—N1—H1N | 119.00 | F1'—C13—C14 | 122.5 (4) |
N2—N1—H1N | 119.00 | C9—C14—C13 | 120.06 |
C6—C1—C7 | 125.3 (4) | C1—C2—H2 | 119.00 |
C2—C1—C7 | 117.4 (4) | C3—C2—H2 | 119.00 |
C2—C1—C6 | 117.3 (4) | C2—C3—H3 | 120.00 |
C1—C2—C3 | 122.0 (4) | C4—C3—H3 | 120.00 |
C2—C3—C4 | 120.3 (4) | C3—C4—H4 | 120.00 |
C3—C4—C5 | 119.7 (4) | C5—C4—H4 | 120.00 |
C4—C5—C6 | 120.6 (4) | C4—C5—H5 | 120.00 |
C1—C6—C5 | 120.2 (4) | C6—C5—H5 | 120.00 |
O1—C6—C1 | 119.9 (4) | N2—C8—H8 | 118.00 |
O1—C6—C5 | 120.0 (3) | C9—C8—H8 | 118.00 |
O2—C7—N1 | 121.6 (4) | C9—C10—H10 | 120.00 |
O2—C7—C1 | 121.4 (4) | C11—C10—H10 | 120.00 |
N1—C7—C1 | 117.0 (4) | C10—C11—H11 | 120.00 |
N2—C8—C9 | 123.2 (4) | C12—C11—H11 | 120.00 |
C10—C9—C14 | 119.98 | C11—C12—H12 | 120.00 |
C8—C9—C14 | 117.4 (3) | C13—C12—H12 | 120.00 |
C8—C9—C10 | 122.6 (3) | C12—C13—H13 | 120.00 |
C9—C10—C11 | 119.97 | C14—C13—H13 | 120.00 |
F1—C11—C10 | 126.5 (4) | C9—C14—H14 | 120.00 |
C10—C11—C12 | 120.04 | C13—C14—H14 | 120.00 |
F1—C11—C12 | 113.4 (4) | ||
C7—N1—N2—C8 | 175.7 (4) | C4—C5—C6—O1 | 178.9 (4) |
N2—N1—C7—O2 | −0.8 (7) | C4—C5—C6—C1 | −0.1 (6) |
N2—N1—C7—C1 | 179.0 (4) | N2—C8—C9—C10 | −1.7 (6) |
N1—N2—C8—C9 | 178.6 (4) | N2—C8—C9—C14 | 178.1 (4) |
C2—C1—C6—C5 | 0.8 (6) | C8—C9—C10—C11 | 179.7 (3) |
C7—C1—C6—O1 | 2.7 (6) | C14—C9—C10—C11 | −0.02 |
C7—C1—C6—C5 | −178.3 (4) | C8—C9—C14—C13 | −179.7 (3) |
C2—C1—C7—O2 | −4.8 (6) | C10—C9—C14—C13 | −0.03 |
C2—C1—C7—N1 | 175.4 (4) | C9—C10—C11—F1 | −177.2 (5) |
C6—C1—C7—O2 | 174.3 (4) | C9—C10—C11—C12 | 0.03 |
C6—C1—C7—N1 | −5.5 (6) | F1—C11—C12—C13 | 177.5 (4) |
C2—C1—C6—O1 | −178.2 (4) | C10—C11—C12—C13 | −0.02 |
C6—C1—C2—C3 | −0.8 (7) | C11—C12—C13—F1' | −178.6 (5) |
C7—C1—C2—C3 | 178.3 (4) | C11—C12—C13—C14 | −0.02 |
C1—C2—C3—C4 | 0.2 (7) | F1'—C13—C14—C9 | 178.5 (5) |
C2—C3—C4—C5 | 0.5 (7) | C12—C13—C14—C9 | 0.03 |
C3—C4—C5—C6 | −0.6 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1 | 0.86 | 1.91 | 2.612 (5) | 138 |
O1—H1O···O2i | 0.82 | 1.86 | 2.657 (5) | 166 |
Symmetry code: (i) x+1/2, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H11FN2O2 |
Mr | 258.25 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 297 |
a, b, c (Å) | 4.8751 (15), 22.188 (7), 11.323 (3) |
β (°) | 96.717 (5) |
V (Å3) | 1216.4 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.20 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.979, 0.989 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8534, 2152, 1205 |
Rint | 0.081 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.088, 0.240, 1.05 |
No. of reflections | 2152 |
No. of parameters | 170 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.30 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1 | 0.86 | 1.91 | 2.612 (5) | 138 |
O1—H1O···O2i | 0.82 | 1.86 | 2.657 (5) | 166 |
Symmetry code: (i) x+1/2, −y+1/2, z−1/2. |
Hydrazones and Schiff bases have attracted much attention for their excellent biological properties, especially for their potential pharmacological and antitumor properties (Kucukguzel et al., 2006; Khattab, 2005; Karthikeyan et al., 2006; Okabe et al., 1993). As part of an ongoing study of such compounds, we report here on the crystal structure of the title compound.
The molecular structure of the title compound is shown in Fig. 1. It can be seen to display a trans configuration about the C=N bond. There is an intramolecular N-H···O hydrogen bond, involving the NH H-atom and the O-atom of the hydroxyl substituent (Table 1), and the dihedral angle between the two benzene rings is 12.5 (2)°.
In the crystal molecules are linked by intermolecular O—H···O hydrongen bonds to form chains running parallel to the c axis (Fig. 2 and Table 1).