Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045989/at2402sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045989/at2402Isup2.hkl |
CCDC reference: 663825
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.049
- wR factor = 0.143
- Data-to-parameter ratio = 11.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.64 mm PLAT480_ALERT_4_C Long H...A H-Bond Reported H4 .. F1 .. 2.63 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H7 .. F1 .. 2.79 Ang. PLAT481_ALERT_4_C Long D...A H-Bond Reported C7 .. F1 .. 3.68 Ang.
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C14 H10 F2 N2 Atom count from _chemical_formula_moiety:C14 H10 F2 N2 O1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Albayrak et al. (2005); Armstrong et al. (1998); Duan et al. (2005); Ersanlı, Odabaşoğlu et al. (2004); Etter (1990); Kazak et al. (2004); Kesslen & Euler (1999); Küçükgüzel et al. (1999); Kundu et al. (2005); Odabaşoğlu et al. (2005); Rollas et al. (2002); Xu & Hu (2007); Xu et al. (1997); Yüce et al. (2004); Özek et al. (2007); Ersanlı, Albayrak et al. (2004); Şahin et al. (2005); Sarojini, Narayana et al. (2007); Sarojini, Yathirajan et al. (2007); Zheng et al. (2005a,b). Ersanli, Albayrak and Sarojini refs not cited elsewhere in CIF; OK to retain them here?
A mixture of 4-fluorobenzaldehyde (2.48 g, 0.02 mol) and hydrazine hydrate (0.5 ml, 0.01 mol) in 15 ml of absolute ethyl alcohol containing 2 drops of 4 M sulfuric acid was refluxed for about 3 h. On cooling, the solid separated was filtered and recrystallized from ethyl alcohol [m.p.: 439–441 K]. Analysis for C14H10F2N2: Found (calculated): C 68.65 (68.85), H 4.18 (4.13), N 11.35% (11.47%).
Hydrazones are known to possess antimicrobial, anticonvulsant, analgesic, anti-inflammatory, antiplatelet, antitubercular and antitumoral activities. For example, isonicotinoyl hydrazones are antitubercular; 4-hydroxybenzoic acid [(5-nitro-2-furyl)methylene]-hydrazide (nifuroxazide) is an intestinal antiseptic; 4-fluorobenzoic acid[(5-nitro-2-furyl)methylene]-hydrazide (Rollas et al., 2002) and 2,3,4-pentanetrione-3-[4-[[(5-nitro-2-furyl) methylene]hydrazino]carbonyl]phenyl]-hydrazone (Küçükgüzel et al., 1999) have antibacterial activity. A number of azine compounds containing both a diimine linkage and an N—N bond have been investigated in terms of their crystallography and coordination chemistry (Kundu et al., 2005; Kesslen & Euler, 1999; Armstrong et al., 1998; Xu et al., 1997). The crystal structures of N,N-bis(4-chlorobenzylidene)hydrazine (Zheng et al., 2005a), N,N'-bis (3-nitrobenzylidene)hydrazine (Zheng et al., 2005b), N,N'-bis(3-hydroxy-4- methoxybenzylidene)hydrazine (Duan et al., 2005), 1,2-bis[4-(trifluoromethyl) benzylidene]hydrazine (Xu & Hu, 2007) have been reported. A new hydrazone, (I), C14H10F2N2 was synthesized and its crystal structure is reported.
The N1═C1 bond length of 1.266 (2) Å is typical of a double bond and similar to the corresponding bond lengths in our previous works (Odabaşoğlu et al., 2005; Albayrak et al., 2005; Şahin et al., 2005; Kazak et al., 2004; Ersanlı, Odabaşoğlu et al.,2004, b; Yüce et al., 2004; Özek et al., 2007). The N—N bond length of 1.410 (3) Å is typical of a Nsp2—Nsp2 single bond.
The crystal structure of (I) is stabilized by three C—H···F intermolecular hydrogen bonds (Table 1). The C—H···F hydrogen bonds generate edge-fussed R21(6)R32(15)R22(8)R32(17) ring motifs (Fig. 2) (Etter, 1990). The molecule is almost planar. There are no C—H···π and π···π interactions in crystal packing.
For related literature, see: Albayrak et al. (2005); Armstrong et al. (1998); Duan et al. (2005); Ersanlı, Odabaşoğlu et al. (2004); Etter (1990); Kazak et al. (2004); Kesslen & Euler (1999); Küçükgüzel et al. (1999); Kundu et al. (2005); Odabaşoğlu et al. (2005); Rollas et al. (2002); Xu & Hu (2007); Xu et al. (1997); Yüce et al. (2004); Özek et al. (2007); Ersanlı, Albayrak et al. (2004); Şahin et al. (2005); Sarojini, Narayana et al. (2007); Sarojini, Yathirajan et al. (2007); Zheng et al. (2005a,b). Ersanli, Albayrak and Sarojini refs not cited elsewhere in CIF; OK to retain them here?
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C14H10F2N2 | F(000) = 252 |
Mr = 244.24 | Dx = 1.397 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2956 reflections |
a = 3.8488 (18) Å | θ = 2.4–27.8° |
b = 13.629 (5) Å | µ = 0.11 mm−1 |
c = 11.083 (5) Å | T = 296 K |
β = 93.17 (4)° | Prism, light yellow |
V = 580.5 (4) Å3 | 0.64 × 0.42 × 0.31 mm |
Z = 2 |
Stoe IPDSII diffractometer | 1136 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 804 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.057 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 2.4° |
ω scans | h = −4→4 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −16→16 |
Tmin = 0.957, Tmax = 0.983 | l = −9→13 |
2956 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | All H-atom parameters refined |
wR(F2) = 0.143 | w = 1/[σ2(Fo2) + (0.0881P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
1136 reflections | Δρmax = 0.15 e Å−3 |
103 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.044 (11) |
C14H10F2N2 | V = 580.5 (4) Å3 |
Mr = 244.24 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 3.8488 (18) Å | µ = 0.11 mm−1 |
b = 13.629 (5) Å | T = 296 K |
c = 11.083 (5) Å | 0.64 × 0.42 × 0.31 mm |
β = 93.17 (4)° |
Stoe IPDSII diffractometer | 1136 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 804 reflections with I > 2σ(I) |
Tmin = 0.957, Tmax = 0.983 | Rint = 0.057 |
2956 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.143 | All H-atom parameters refined |
S = 1.03 | Δρmax = 0.15 e Å−3 |
1136 reflections | Δρmin = −0.19 e Å−3 |
103 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.6680 (5) | 0.41276 (12) | 0.59066 (17) | 0.0559 (5) | |
C2 | 0.7183 (4) | 0.30733 (12) | 0.60689 (16) | 0.0499 (5) | |
C3 | 0.6028 (5) | 0.24038 (13) | 0.51855 (18) | 0.0561 (5) | |
C4 | 0.6501 (5) | 0.14112 (12) | 0.53589 (19) | 0.0620 (5) | |
C5 | 0.8109 (5) | 0.10995 (12) | 0.64283 (18) | 0.0605 (5) | |
C6 | 0.9276 (5) | 0.17279 (14) | 0.73247 (19) | 0.0618 (5) | |
C7 | 0.8812 (5) | 0.27196 (13) | 0.71346 (18) | 0.0587 (5) | |
N1 | 0.5085 (4) | 0.44837 (9) | 0.49769 (14) | 0.0590 (5) | |
F1 | 0.8551 (4) | 0.01213 (8) | 0.65970 (13) | 0.0915 (6) | |
H1 | 0.775 (5) | 0.4584 (15) | 0.658 (2) | 0.073 (6)* | |
H3 | 0.485 (5) | 0.2631 (13) | 0.445 (2) | 0.060 (5)* | |
H4 | 0.577 (6) | 0.0952 (18) | 0.476 (2) | 0.091 (7)* | |
H6 | 1.027 (6) | 0.1472 (15) | 0.804 (2) | 0.083 (7)* | |
H7 | 0.965 (6) | 0.3201 (19) | 0.776 (2) | 0.090 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0635 (10) | 0.0470 (9) | 0.0560 (10) | −0.0012 (7) | −0.0063 (9) | −0.0003 (8) |
C2 | 0.0525 (9) | 0.0453 (8) | 0.0513 (9) | 0.0006 (6) | −0.0031 (7) | 0.0005 (7) |
C3 | 0.0645 (10) | 0.0492 (9) | 0.0530 (10) | 0.0010 (7) | −0.0115 (8) | 0.0003 (7) |
C4 | 0.0764 (12) | 0.0471 (10) | 0.0605 (12) | −0.0004 (8) | −0.0141 (10) | −0.0053 (8) |
C5 | 0.0721 (11) | 0.0426 (9) | 0.0655 (12) | 0.0026 (8) | −0.0088 (9) | 0.0031 (8) |
C6 | 0.0717 (11) | 0.0550 (10) | 0.0567 (11) | 0.0026 (8) | −0.0150 (9) | 0.0046 (8) |
C7 | 0.0682 (11) | 0.0507 (10) | 0.0554 (11) | −0.0012 (8) | −0.0117 (8) | −0.0039 (8) |
N1 | 0.0733 (10) | 0.0393 (7) | 0.0630 (10) | 0.0023 (6) | −0.0098 (7) | −0.0005 (6) |
F1 | 0.1328 (12) | 0.0434 (6) | 0.0940 (11) | 0.0087 (6) | −0.0326 (8) | 0.0052 (6) |
C1—N1 | 1.266 (2) | C4—H4 | 0.94 (3) |
C1—C2 | 1.460 (2) | C5—F1 | 1.356 (2) |
C1—H1 | 1.04 (2) | C5—C6 | 1.368 (3) |
C2—C7 | 1.392 (3) | C6—C7 | 1.378 (3) |
C2—C3 | 1.393 (3) | C6—H6 | 0.93 (3) |
C3—C4 | 1.377 (2) | C7—H7 | 1.00 (3) |
C3—H3 | 0.96 (2) | N1—N1i | 1.410 (3) |
C4—C5 | 1.374 (3) | ||
N1—C1—C2 | 122.17 (16) | C3—C4—H4 | 121.5 (16) |
N1—C1—H1 | 120.8 (12) | F1—C5—C6 | 118.79 (17) |
C2—C1—H1 | 117.0 (12) | F1—C5—C4 | 118.04 (15) |
C7—C2—C3 | 118.74 (17) | C6—C5—C4 | 123.16 (17) |
C7—C2—C1 | 119.72 (15) | C5—C6—C7 | 117.92 (18) |
C3—C2—C1 | 121.54 (16) | C5—C6—H6 | 119.2 (14) |
C4—C3—C2 | 120.71 (18) | C7—C6—H6 | 122.9 (14) |
C4—C3—H3 | 119.1 (11) | C6—C7—C2 | 121.18 (18) |
C2—C3—H3 | 120.2 (11) | C6—C7—H7 | 120.3 (15) |
C5—C4—C3 | 118.29 (17) | C2—C7—H7 | 118.5 (15) |
C5—C4—H4 | 120.2 (15) | C1—N1—N1i | 111.98 (18) |
N1—C1—C2—C7 | −176.97 (19) | F1—C5—C6—C7 | 179.80 (18) |
N1—C1—C2—C3 | 2.2 (3) | C4—C5—C6—C7 | −0.2 (3) |
C7—C2—C3—C4 | −0.3 (3) | C5—C6—C7—C2 | 0.5 (3) |
C1—C2—C3—C4 | −179.46 (18) | C3—C2—C7—C6 | −0.2 (3) |
C2—C3—C4—C5 | 0.6 (3) | C1—C2—C7—C6 | 178.91 (18) |
C3—C4—C5—F1 | 179.65 (18) | C2—C1—N1—N1i | 179.84 (17) |
C3—C4—C5—C6 | −0.4 (3) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···F1ii | 1.04 (2) | 2.52 (2) | 3.507 (3) | 159.36 (1) |
C4—H4···F1iii | 0.94 (2) | 2.63 (2) | 3.518 (3) | 157.98 (2) |
C7—H7···F1ii | 1.00 (2) | 2.79 (3) | 3.683 (3) | 149.43 (2) |
Symmetry codes: (ii) −x+2, y+1/2, −z+3/2; (iii) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C14H10F2N2 |
Mr | 244.24 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 3.8488 (18), 13.629 (5), 11.083 (5) |
β (°) | 93.17 (4) |
V (Å3) | 580.5 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.64 × 0.42 × 0.31 |
Data collection | |
Diffractometer | Stoe IPDSII |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.957, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2956, 1136, 804 |
Rint | 0.057 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.143, 1.03 |
No. of reflections | 1136 |
No. of parameters | 103 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.15, −0.19 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···F1i | 1.04 (2) | 2.52 (2) | 3.507 (3) | 159.36 (1) |
C4—H4···F1ii | 0.94 (2) | 2.63 (2) | 3.518 (3) | 157.98 (2) |
C7—H7···F1i | 1.00 (2) | 2.79 (3) | 3.683 (3) | 149.43 (2) |
Symmetry codes: (i) −x+2, y+1/2, −z+3/2; (ii) −x+1, −y, −z+1. |
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Hydrazones are known to possess antimicrobial, anticonvulsant, analgesic, anti-inflammatory, antiplatelet, antitubercular and antitumoral activities. For example, isonicotinoyl hydrazones are antitubercular; 4-hydroxybenzoic acid [(5-nitro-2-furyl)methylene]-hydrazide (nifuroxazide) is an intestinal antiseptic; 4-fluorobenzoic acid[(5-nitro-2-furyl)methylene]-hydrazide (Rollas et al., 2002) and 2,3,4-pentanetrione-3-[4-[[(5-nitro-2-furyl) methylene]hydrazino]carbonyl]phenyl]-hydrazone (Küçükgüzel et al., 1999) have antibacterial activity. A number of azine compounds containing both a diimine linkage and an N—N bond have been investigated in terms of their crystallography and coordination chemistry (Kundu et al., 2005; Kesslen & Euler, 1999; Armstrong et al., 1998; Xu et al., 1997). The crystal structures of N,N-bis(4-chlorobenzylidene)hydrazine (Zheng et al., 2005a), N,N'-bis (3-nitrobenzylidene)hydrazine (Zheng et al., 2005b), N,N'-bis(3-hydroxy-4- methoxybenzylidene)hydrazine (Duan et al., 2005), 1,2-bis[4-(trifluoromethyl) benzylidene]hydrazine (Xu & Hu, 2007) have been reported. A new hydrazone, (I), C14H10F2N2 was synthesized and its crystal structure is reported.
The N1═C1 bond length of 1.266 (2) Å is typical of a double bond and similar to the corresponding bond lengths in our previous works (Odabaşoğlu et al., 2005; Albayrak et al., 2005; Şahin et al., 2005; Kazak et al., 2004; Ersanlı, Odabaşoğlu et al.,2004, b; Yüce et al., 2004; Özek et al., 2007). The N—N bond length of 1.410 (3) Å is typical of a Nsp2—Nsp2 single bond.
The crystal structure of (I) is stabilized by three C—H···F intermolecular hydrogen bonds (Table 1). The C—H···F hydrogen bonds generate edge-fussed R21(6)R32(15)R22(8)R32(17) ring motifs (Fig. 2) (Etter, 1990). The molecule is almost planar. There are no C—H···π and π···π interactions in crystal packing.