N'-(4-Fluoro-benzyl-idene)-3,4,5-trimethoxy-benzohydrazide.

The title compound, C(17)H(17)FN(2)O(4), is of inter-est due to its potential pharmaceutical and agrochemical activity. All three meth-oxy 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 mol-ecule. Inter-molecular N-H⋯O hydrogen bonds link the mol-ecules 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 = 332.33

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.104

S = 1.07

3558 reflections

220 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.20 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H17FN2O4	F000 = 696
Mr = 332.33	Dx = 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 = 2.7–27.0º
b = 26.2496 (13) Å	µ = 0.11 mm−1
c = 8.1271 (4) Å	T = 173 (2) K
β = 105.5470 (10)º	Block, colorless
V = 1627.65 (14) Å3	0.48 × 0.37 × 0.25 mm
Z = 4

Bruker SMART 1000 CCD diffractometer	3558 independent reflections
Radiation source: fine-focus sealed tube	2856 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.018
T = 173(2) K	θmax = 27.1º
ω scans	θmin = 2.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)	h = −10→6
Tmin = 0.935, Tmax = 0.974	k = −33→33
9603 measured reflections	l = −10→10

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.0561P)2 + 0.3099P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
3558 reflections	Δρmax = 0.27 e Å−3
220 parameters	Δρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.63386 (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)

	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)

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)

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

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) .