N′-(4-Fluoro­benzyl­idene)-3,4,5-trimethoxy­benzohydrazide

He, D.-H.; Zhu, Y.-C.; Yang, Z.-R.

doi:10.1107/S1600536808023702

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1648

doi:10.1107/S1600536808023702

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N′-(4-Fluorobenzylidene)-3,4,5-trimethoxybenzohydrazide

Dao-Hang He,^a ^* Yong-Chuang Zhu ^a and Zhuo-Ru Yang ^a

^aSchool of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, People's Republic of China
^*Correspondence e-mail: daohanghe@yahoo.com.cn

(Received 8 July 2008; accepted 27 July 2008; online 31 July 2008)

The title compound, C₁₇H₁₇FN₂O₄, is of interest due to its potential pharmaceutical and agrochemical activity. All three methoxy groups are twisted with respect to the attached aromatic ring [C—C—O—C torsion angles = 10.43 (18), 97.38 (14), −19.34 (17)°] and the phenyl ring makes a dihedral angle of 40.6 (2)° with the plane through the remaining atoms in the molecule. Intermolecular N—H⋯O hydrogen bonds link the molecules into chains running along the c axis.

Related literature

For related literature, see: Bernardino et al. (2006 ); Ganjali et al. (2006 ); Gardner et al. (1991 ); Lin et al. (2005 ); Patole et al. (2003 ); Liu et al. (2006 ); Zhou et al. (2005 ).

Experimental

Crystal data

C₁₇H₁₇FN₂O₄
M_r = 332.33
Monoclinic, P 2₁ /c
a = 7.9194 (4) Å
b = 26.2496 (13) Å
c = 8.1271 (4) Å
β = 105.5470 (10)°
V = 1627.65 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 173 (2) K
0.48 × 0.37 × 0.25 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.935, T_max = 0.974
9603 measured reflections
3558 independent reflections
2856 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.104
S = 1.07
3558 reflections
220 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4ⁱ	0.88	1.96	2.8238 (13)	167
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2003 ); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536808023702/fl2210sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808023702/fl2210Isup2.hkl

checkCIF report

Comment top

Molecules involving Schiff bases are of interest due to their biological activity as pharmaceuticals and agrochemicals (Bernardino et al., 2006; Ganjali et al., 2006; Gardner et al., 1991; Patole et al., 2003;). In addition, Schiff base ligands have attracted much attention because they can readily form stable complexes with most metal ions (Lin et al., 2005; Zhou et al., 2005). We report herein the synthesis and crystal structure of the Schiff base compound (I), obtained by the condensation of 3,4,5-trimethoxybenzohydrazide and 4-fluorobenzaldehyde.

All three methoxy groups are twisted with respect their attached aromatic ring (10.41°, 97.38°, -19.34°, respectively) and the phenyl ring itself makes a dihedral angle of 40.64° with the plane through the remaining atoms (C7 through F1) in the molecule(Fig. 1). Similar geometry has been observed in a related hydrazone analogue (Liu et al., 2006). The bond lengths and bond angles are within normal ranges. Intermolecular N—H···O hydrogen bonds link the molecules into chains running along the c axis that help stabilize the molecular structure (Fig. 2).

Related literature top

For related literature, see: Bernardino et al. (2006); Ganjali et al. (2006); Gardner et al. (1991); Lin et al. (2005); Patole et al. (2003); Liu et al. (2006); Zhou et al. (2005).

Experimental top

A mixture of 3,4,5-trimethoxybenzohydrazide (1 mmol) and 4-fluorobenzaldehyde (1 mmol) in anhydrous ethanol (10 ml) was refluxed at 80 °C for 2 h. When the solution was cooled to room temperature(25 °C), some white needles separated out. After filtration, colorless single crystals suitable for X-ray analysis were obtained by slow evaporation of a methanol solution at room temperature.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The Structure of the title compound, with the atom numbering. Displacement ellipsoids are the 50% probability level.
	Fig. 2. The packing of the title compound, viewed down the a axis. The dashed lines represent the hydrogen bonding interactions.

(I) top

Crystal data top

C₁₇H₁₇FN₂O₄	F(000) = 696
M_r = 332.33	D_x = 1.356 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5449 reflections
a = 7.9194 (4) Å	θ = 2.7–27.0°
b = 26.2496 (13) Å	µ = 0.11 mm⁻¹
c = 8.1271 (4) Å	T = 173 K
β = 105.547 (1)°	Block, colorless
V = 1627.65 (14) Å³	0.48 × 0.37 × 0.25 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD diffractometer	3558 independent reflections
Radiation source: fine-focus sealed tube	2856 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ω scans	θ_max = 27.1°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −10→6
T_min = 0.935, T_max = 0.974	k = −33→33
9603 measured reflections	l = −10→10

Refinement top

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0561P)² + 0.3099P] where P = (F_o² + 2F_c²)/3
3558 reflections	(Δ/σ)_max = 0.001
220 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₇H₁₇FN₂O₄	V = 1627.65 (14) Å³
M_r = 332.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.9194 (4) Å	µ = 0.11 mm⁻¹
b = 26.2496 (13) Å	T = 173 K
c = 8.1271 (4) Å	0.48 × 0.37 × 0.25 mm
β = 105.547 (1)°

Data collection top

Bruker SMART 1000 CCD diffractometer	3558 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2856 reflections with I > 2σ(I)
T_min = 0.935, T_max = 0.974	R_int = 0.018
9603 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.07	Δρ_max = 0.27 e Å⁻³
3558 reflections	Δρ_min = −0.21 e Å⁻³
220 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.63386 (15)	0.68413 (4)	0.23670 (15)	0.0213 (3)
C2	0.65648 (16)	0.63159 (5)	0.23753 (15)	0.0234 (3)
H2	0.7222	0.6148	0.3378	0.028*
C3	0.58205 (16)	0.60404 (5)	0.09044 (16)	0.0242 (3)
C4	0.48089 (16)	0.62887 (5)	−0.05539 (15)	0.0240 (3)
C5	0.44513 (15)	0.68070 (5)	−0.04828 (15)	0.0233 (3)
C6	0.52479 (15)	0.70882 (4)	0.09643 (15)	0.0222 (3)
H6	0.5051	0.7445	0.0997	0.027*
C7	0.73648 (15)	0.71281 (4)	0.39003 (15)	0.0214 (2)
C8	0.94162 (16)	0.83150 (5)	0.43795 (16)	0.0249 (3)
H8	0.9218	0.8379	0.3192	0.030*
C9	1.03374 (16)	0.86967 (5)	0.56060 (16)	0.0249 (3)
C10	1.06439 (16)	0.86332 (5)	0.73717 (17)	0.0274 (3)
H10	1.0287	0.8327	0.7804	0.033*
C11	1.14578 (19)	0.90092 (5)	0.84950 (18)	0.0335 (3)
H11	1.1672	0.8965	0.9694	0.040*
C12	1.19497 (19)	0.94501 (5)	0.78240 (19)	0.0365 (3)
C13	1.1702 (2)	0.95280 (5)	0.6106 (2)	0.0373 (3)
H13	1.2076	0.9834	0.5690	0.045*
C14	1.08883 (19)	0.91458 (5)	0.49972 (18)	0.0324 (3)
H14	1.0704	0.9191	0.3802	0.039*
C15	0.6792 (2)	0.52504 (5)	0.22518 (19)	0.0372 (3)
H15A	0.8023	0.5352	0.2688	0.056*
H15B	0.6727	0.4885	0.1999	0.056*
H15C	0.6166	0.5324	0.3114	0.056*
C16	0.5363 (2)	0.59696 (6)	−0.30234 (19)	0.0423 (4)
H16A	0.5561	0.6304	−0.3474	0.063*
H16B	0.4903	0.5734	−0.3974	0.063*
H16C	0.6472	0.5838	−0.2300	0.063*
C17	0.25329 (17)	0.74833 (5)	−0.17173 (17)	0.0300 (3)
H17A	0.2088	0.7471	−0.0703	0.045*
H17B	0.1561	0.7551	−0.2729	0.045*
H17C	0.3406	0.7755	−0.1584	0.045*
F1	1.27194 (14)	0.98260 (3)	0.89208 (12)	0.0556 (3)
N1	0.79692 (13)	0.75849 (4)	0.35482 (12)	0.0224 (2)
H1	0.7790	0.7684	0.2481	0.027*
N2	0.88701 (13)	0.78964 (4)	0.48641 (13)	0.0225 (2)
O1	0.60103 (13)	0.55283 (3)	0.07321 (12)	0.0323 (2)
O2	0.41211 (12)	0.60182 (3)	−0.20300 (11)	0.0294 (2)
O3	0.33239 (12)	0.70067 (3)	−0.19160 (11)	0.0308 (2)
O4	0.76599 (13)	0.69488 (3)	0.53497 (11)	0.0292 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0232 (6)	0.0219 (6)	0.0196 (6)	−0.0017 (5)	0.0073 (5)	−0.0015 (4)
C2	0.0266 (6)	0.0214 (6)	0.0214 (6)	−0.0002 (5)	0.0049 (5)	0.0018 (5)
C3	0.0279 (6)	0.0181 (6)	0.0265 (6)	−0.0025 (5)	0.0071 (5)	−0.0009 (5)
C4	0.0250 (6)	0.0233 (6)	0.0224 (6)	−0.0051 (5)	0.0040 (5)	−0.0036 (5)
C5	0.0218 (6)	0.0253 (6)	0.0216 (6)	−0.0008 (5)	0.0038 (5)	0.0020 (5)
C6	0.0243 (6)	0.0188 (6)	0.0236 (6)	0.0000 (5)	0.0067 (5)	0.0000 (5)
C7	0.0248 (6)	0.0208 (6)	0.0186 (6)	0.0033 (5)	0.0059 (5)	−0.0009 (4)
C8	0.0272 (6)	0.0243 (6)	0.0217 (6)	0.0010 (5)	0.0039 (5)	−0.0024 (5)
C9	0.0222 (6)	0.0220 (6)	0.0289 (7)	0.0012 (5)	0.0040 (5)	−0.0035 (5)
C10	0.0257 (6)	0.0251 (6)	0.0296 (7)	−0.0002 (5)	0.0044 (5)	−0.0019 (5)
C11	0.0352 (7)	0.0342 (7)	0.0276 (7)	−0.0028 (6)	0.0026 (6)	−0.0050 (6)
C12	0.0365 (8)	0.0271 (7)	0.0398 (8)	−0.0053 (6)	−0.0002 (6)	−0.0114 (6)
C13	0.0407 (8)	0.0254 (7)	0.0429 (8)	−0.0066 (6)	0.0061 (6)	0.0000 (6)
C14	0.0369 (7)	0.0286 (7)	0.0295 (7)	−0.0027 (6)	0.0054 (6)	0.0002 (5)
C15	0.0513 (9)	0.0191 (6)	0.0347 (8)	0.0005 (6)	0.0004 (6)	0.0027 (5)
C16	0.0440 (9)	0.0516 (9)	0.0317 (8)	−0.0087 (7)	0.0109 (7)	−0.0147 (7)
C17	0.0272 (7)	0.0311 (7)	0.0302 (7)	0.0052 (5)	0.0049 (5)	0.0054 (5)
F1	0.0731 (7)	0.0357 (5)	0.0470 (6)	−0.0186 (5)	−0.0030 (5)	−0.0153 (4)
N1	0.0281 (5)	0.0222 (5)	0.0156 (5)	−0.0024 (4)	0.0034 (4)	−0.0018 (4)
N2	0.0227 (5)	0.0221 (5)	0.0208 (5)	0.0009 (4)	0.0026 (4)	−0.0048 (4)
O1	0.0456 (6)	0.0178 (4)	0.0289 (5)	−0.0011 (4)	0.0021 (4)	−0.0013 (4)
O2	0.0314 (5)	0.0283 (5)	0.0252 (5)	−0.0056 (4)	0.0018 (4)	−0.0067 (4)
O3	0.0347 (5)	0.0280 (5)	0.0235 (5)	0.0041 (4)	−0.0028 (4)	0.0004 (4)
O4	0.0448 (6)	0.0223 (4)	0.0186 (4)	−0.0007 (4)	0.0055 (4)	0.0006 (3)

Geometric parameters (Å, º) top

C1—C2	1.3905 (17)	C11—C12	1.379 (2)
C1—C6	1.3921 (17)	C11—H11	0.9500
C1—C7	1.4957 (16)	C12—F1	1.3596 (15)
C2—C3	1.3862 (17)	C12—C13	1.372 (2)
C2—H2	0.9500	C13—C14	1.3866 (19)
C3—O1	1.3639 (14)	C13—H13	0.9500
C3—C4	1.4008 (17)	C14—H14	0.9500
C4—O2	1.3748 (14)	C15—O1	1.4252 (16)
C4—C5	1.3941 (17)	C15—H15A	0.9800
C5—O3	1.3679 (14)	C15—H15B	0.9800
C5—C6	1.3886 (16)	C15—H15C	0.9800
C6—H6	0.9500	C16—O2	1.4354 (17)
C7—O4	1.2312 (14)	C16—H16A	0.9800
C7—N1	1.3499 (15)	C16—H16B	0.9800
C8—N2	1.2808 (16)	C16—H16C	0.9800
C8—C9	1.4629 (17)	C17—O3	1.4276 (15)
C8—H8	0.9500	C17—H17A	0.9800
C9—C14	1.3931 (18)	C17—H17B	0.9800
C9—C10	1.3997 (18)	C17—H17C	0.9800
C10—C11	1.3812 (18)	N1—N2	1.3829 (13)
C10—H10	0.9500	N1—H1	0.8800

C2—C1—C6	121.11 (11)	F1—C12—C11	118.32 (13)
C2—C1—C7	117.04 (10)	C13—C12—C11	123.28 (13)
C6—C1—C7	121.82 (10)	C12—C13—C14	117.94 (13)
C3—C2—C1	119.26 (11)	C12—C13—H13	121.0
C3—C2—H2	120.4	C14—C13—H13	121.0
C1—C2—H2	120.4	C13—C14—C9	121.10 (13)
O1—C3—C2	124.72 (11)	C13—C14—H14	119.5
O1—C3—C4	115.18 (11)	C9—C14—H14	119.5
C2—C3—C4	120.10 (11)	O1—C15—H15A	109.5
O2—C4—C5	120.19 (11)	O1—C15—H15B	109.5
O2—C4—C3	120.06 (11)	H15A—C15—H15B	109.5
C5—C4—C3	119.70 (11)	O1—C15—H15C	109.5
O3—C5—C6	124.21 (11)	H15A—C15—H15C	109.5
O3—C5—C4	115.61 (10)	H15B—C15—H15C	109.5
C6—C5—C4	120.17 (11)	O2—C16—H16A	109.5
C5—C6—C1	119.17 (11)	O2—C16—H16B	109.5
C5—C6—H6	120.4	H16A—C16—H16B	109.5
C1—C6—H6	120.4	O2—C16—H16C	109.5
O4—C7—N1	123.72 (11)	H16A—C16—H16C	109.5
O4—C7—C1	121.75 (11)	H16B—C16—H16C	109.5
N1—C7—C1	114.51 (10)	O3—C17—H17A	109.5
N2—C8—C9	121.72 (11)	O3—C17—H17B	109.5
N2—C8—H8	119.1	H17A—C17—H17B	109.5
C9—C8—H8	119.1	O3—C17—H17C	109.5
C14—C9—C10	118.70 (12)	H17A—C17—H17C	109.5
C14—C9—C8	118.95 (12)	H17B—C17—H17C	109.5
C10—C9—C8	122.33 (12)	C7—N1—N2	120.01 (9)
C11—C10—C9	120.96 (13)	C7—N1—H1	120.0
C11—C10—H10	119.5	N2—N1—H1	120.0
C9—C10—H10	119.5	C8—N2—N1	114.60 (10)
C12—C11—C10	118.01 (13)	C3—O1—C15	116.73 (10)
C12—C11—H11	121.0	C4—O2—C16	111.45 (10)
C10—C11—H11	121.0	C5—O3—C17	116.46 (10)
F1—C12—C13	118.41 (13)

C6—C1—C2—C3	6.01 (18)	N2—C8—C9—C10	−1.37 (19)
C7—C1—C2—C3	−171.90 (11)	C14—C9—C10—C11	0.73 (19)
C1—C2—C3—O1	177.13 (12)	C8—C9—C10—C11	−177.48 (12)
C1—C2—C3—C4	−1.92 (18)	C9—C10—C11—C12	0.4 (2)
O1—C3—C4—O2	−1.36 (17)	C10—C11—C12—F1	178.69 (12)
C2—C3—C4—O2	177.77 (11)	C10—C11—C12—C13	−1.3 (2)
O1—C3—C4—C5	176.35 (11)	F1—C12—C13—C14	−178.91 (13)
C2—C3—C4—C5	−4.53 (18)	C11—C12—C13—C14	1.1 (2)
O2—C4—C5—O3	3.48 (17)	C12—C13—C14—C9	0.1 (2)
C3—C4—C5—O3	−174.22 (11)	C10—C9—C14—C13	−1.0 (2)
O2—C4—C5—C6	−175.29 (11)	C8—C9—C14—C13	177.31 (12)
C3—C4—C5—C6	7.01 (18)	O4—C7—N1—N2	−4.82 (18)
O3—C5—C6—C1	178.34 (11)	C1—C7—N1—N2	177.12 (9)
C4—C5—C6—C1	−3.01 (17)	C9—C8—N2—N1	177.75 (10)
C2—C1—C6—C5	−3.55 (17)	C7—N1—N2—C8	178.47 (11)
C7—C1—C6—C5	174.26 (11)	C2—C3—O1—C15	10.43 (18)
C2—C1—C7—O4	−35.84 (16)	C4—C3—O1—C15	−170.49 (12)
C6—C1—C7—O4	146.27 (12)	C5—C4—O2—C16	97.38 (14)
C2—C1—C7—N1	142.27 (11)	C3—C4—O2—C16	−84.92 (15)
C6—C1—C7—N1	−35.63 (16)	C6—C5—O3—C17	−19.34 (17)
N2—C8—C9—C14	−179.58 (12)	C4—C5—O3—C17	161.96 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ⁱ	0.88	1.96	2.8238 (13)	167

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇FN₂O₄
M_r	332.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	7.9194 (4), 26.2496 (13), 8.1271 (4)
β (°)	105.547 (1)
V (Å³)	1627.65 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.48 × 0.37 × 0.25

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.935, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	9603, 3558, 2856
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.640

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.104, 1.07
No. of reflections	3558
No. of parameters	220
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.21

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2003), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ⁱ	0.88	1.96	2.8238 (13)	166.7

Symmetry code: (i) x, −y+3/2, z−1/2.

Acknowledgements

The authors thank the Natural Science Youth Foundation of South China University of Technology for financial assistance (E5050570).

References

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