(E)-2-[2-(4-Fluoro­benzyl­idene)hydrazinocarbon­yl]-N-isopropyl­benzamide

Liu, M.; Duan, Y.; Wang, Y.; Zhang, W.-X.; Liu, S.

doi:10.1107/S1600536809022181

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1599

doi:10.1107/S1600536809022181

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(E)-2-[2-(4-Fluorobenzylidene)hydrazinocarbonyl]-N-isopropylbenzamide

Ming Liu,^a ^* Yousheng Duan,^a Yi Wang,^a Wen-Xiong Zhang ^b and Shangzhong Liu ^a

^aDepartment of Applied Chemistry, China Agriculture University, 100193 Beijing, People's Republic of China, and ^bCollege of Chemistry and Molecular Engineering, Peking University, 100871 Beijing, People's Republic of China
^*Correspondence e-mail: shangzho@cau.edu.cn

(Received 28 March 2009; accepted 10 June 2009; online 17 June 2009)

The title compound, C₁₈H₁₈FN₃O₂, adopts a trans conformation with respect to the C=N double bond. The dihedral angle between the two benzene rings is: 59.73 (6)°. Two independent N—H⋯O hydrogen bonds link the molecules into layers parallel to (101).

Related literature

For biologically active phthalic diamides, see: Coronado et al. (1994 ); Tohnishi et al. (2000 ). For the preparation of the title compound, see: Zaky (2002 ); Shigeru et al. (2003 ).

Experimental

Crystal data

C₁₈H₁₈FN₃O₂
M_r = 327.35
Monoclinic, P 2₁ /n
a = 13.316 (3) Å
b = 8.8904 (18) Å
c = 14.102 (3) Å
β = 91.10 (3)°
V = 1669.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 123 K
0.30 × 0.30 × 0.30 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi,1995 ) T_min = 0.944, T_max = 0.972
15335 measured reflections
3833 independent reflections
2302 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.069
S = 1.02
3833 reflections
228 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1⋯O2ⁱ	0.875 (15)	2.127 (15)	2.9887 (16)	168.4 (14)
N1—H2⋯O1ⁱⁱ	0.850 (15)	1.976 (15)	2.8256 (16)	177.8 (15)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+2, -z+1.

Data collection: RAPID-AUTO (Rigaku, 2000 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Molecular Structure Corporation and Rigaku, 2000 ); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809022181/ya2090sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809022181/ya2090Isup2.hkl

checkCIF report

Comment top

Phthalic diamides possess insecticidal properties due to their ability to activate ryanodine receptor (Coronado et al., 1994; Tohnishi et al., 2000). The title compound (I), a new phthalic diamide derivative, was synthesized by the condensation of N-aminophthalimide with 4-fluorobenzaldehyde followed by a ring-opening reaction using isopropyl amine (Zaky, 2002; Shigeru et al., 2003).

The molecular structure of the title compound is shown in Fig. 1. Molecule was proved to be a trans -isomer with respect to the C9=N2 double bond.

There are two independent N—H···O bonds (Table 1), which link molecules into the layers parallel to (101) plane (Fig. 2).

Related literature top

For biologically active phthalic diamides, see: Coronado et al. (1994); Tohnishi et al. (2000). For the preparation of the title compound, see: Zaky (2002); Shigeru et al. (2003).

Experimental top

To a solution of N-aminophthalimide (1.62 g, 10 mmol) and 4-fluorobenzaldehyde (1.24 g, 10 mmol) in 1,4-dioxane (100 ml), 12 N HCl (0.1 ml) was added at room temperature. After stirring for 5–10 min, a solution of isopropyl amine (1.16 g, 20 mmol) in 1,4-dioxane (10 ml) was added; the reaction mixture was stirred overnight at room temperature. After the solvent was evaporated under reduced pressure, the resulting mixture was dissolved in ethyl acetate (80 ml), washed with H₂O (3×30 ml) and dried with anhydrous sodium sulfate to give the title compound (2.01 g, 61.5%). Single crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of ethanol solution at room temperature over one week.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2000); cell refinement: RAPID-AUTO (Rigaku, 2000); data reduction: CrystalStructure (Molecular Structure Corporation and Rigaku, 2000); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I); displacement ellipsoids are drawn at the 30% probability level. H atoms are shown as small circles of arbitrary radius.
	Fig. 2. The crystal packing of (I) viewed along the [101] direction; hydrogen bonds are shown as dashed lines.

(E)-2-[2-(4-Fluorobenzylidene)hydrazinocarbonyl]-N- isopropylbenzamide top

Crystal data top

C₁₈H₁₈FN₃O₂	F(000) = 688
M_r = 327.35	D_x = 1.303 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 15335 reflections
a = 13.316 (3) Å	θ = 2.1–27.5°
b = 8.8904 (18) Å	µ = 0.09 mm⁻¹
c = 14.102 (3) Å	T = 123 K
β = 91.10 (3)°	Block, colourless
V = 1669.2 (6) Å³	0.30 × 0.30 × 0.30 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	3833 independent reflections
Radiation source: fine-focus sealed tube	2302 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
Detector resolution: 10.00 pixels mm^-1	θ_max = 27.5°, θ_min = 2.1°
Ω scans	h = −17→17
Absorption correction: multi-scan (ABSCOR; Higashi,1995)	k = −11→11
T_min = 0.944, T_max = 0.972	l = −18→18
15335 measured reflections

Refinement top

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.069	w = 1/[σ²(F_o²) + (0.015P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3833 reflections	Δρ_max = 0.24 e Å⁻³
228 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0285 (8)

Crystal data top

C₁₈H₁₈FN₃O₂	V = 1669.2 (6) Å³
M_r = 327.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.316 (3) Å	µ = 0.09 mm⁻¹
b = 8.8904 (18) Å	T = 123 K
c = 14.102 (3) Å	0.30 × 0.30 × 0.30 mm
β = 91.10 (3)°

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	3833 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi,1995)	2302 reflections with I > 2σ(I)
T_min = 0.944, T_max = 0.972	R_int = 0.046
15335 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.24 e Å⁻³
3833 reflections	Δρ_min = −0.23 e Å⁻³
228 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	0.62786 (10)	0.87434 (17)	0.48465 (10)	0.0197 (3)
C2	0.70864 (10)	0.80962 (16)	0.29308 (10)	0.0179 (3)
C3	0.72241 (10)	0.78555 (15)	0.47071 (10)	0.0168 (3)
C4	0.76143 (10)	0.75512 (15)	0.38154 (10)	0.0162 (3)
C5	0.85500 (10)	0.68578 (15)	0.37629 (10)	0.0197 (3)
H5	0.8819	0.6634	0.3160	0.024*
C6	0.90921 (11)	0.64909 (16)	0.45774 (11)	0.0228 (4)
H6	0.9739	0.6050	0.4531	0.027*
C7	0.86928 (10)	0.67651 (16)	0.54567 (11)	0.0236 (4)
H7	0.9057	0.6494	0.6017	0.028*
C8	0.77595 (10)	0.74366 (16)	0.55190 (10)	0.0216 (4)
H8	0.7482	0.7613	0.6124	0.026*
C9	0.44987 (11)	0.65483 (17)	0.36494 (10)	0.0222 (4)
H9	0.3990	0.7297	0.3628	0.027*
C10	0.43139 (10)	0.50842 (17)	0.32041 (10)	0.0215 (4)
C11	0.35688 (11)	0.49509 (19)	0.24980 (11)	0.0299 (4)
H11	0.3173	0.5803	0.2331	0.036*
C12	0.33975 (12)	0.3594 (2)	0.20378 (12)	0.0384 (5)
H12	0.2904	0.3510	0.1545	0.046*
C13	0.39601 (13)	0.2385 (2)	0.23155 (12)	0.0366 (5)
C14	0.46863 (12)	0.24391 (18)	0.30209 (11)	0.0307 (4)
H14	0.5053	0.1565	0.3202	0.037*
C15	0.48647 (11)	0.38099 (17)	0.34587 (11)	0.0237 (4)
H15	0.5371	0.3882	0.3940	0.028*
C16	0.66213 (10)	0.75633 (16)	0.12683 (10)	0.0221 (4)
H16	0.6111	0.8369	0.1373	0.027*
C17	0.60856 (12)	0.61917 (18)	0.08583 (11)	0.0326 (4)
H17A	0.6574	0.5385	0.0758	0.049*
H17B	0.5762	0.6458	0.0251	0.049*
H17C	0.5576	0.5848	0.1301	0.049*
C18	0.74105 (11)	0.81707 (18)	0.05991 (11)	0.0311 (4)
H18A	0.7736	0.9053	0.0886	0.047*
H18B	0.7087	0.8457	−0.0004	0.047*
H18C	0.7915	0.7392	0.0486	0.047*
F1	0.37958 (8)	0.10376 (12)	0.18747 (7)	0.0603 (4)
N1	0.53997 (9)	0.82179 (14)	0.44990 (9)	0.0204 (3)
N2	0.53387 (8)	0.68275 (13)	0.40673 (8)	0.0196 (3)
N3	0.70850 (9)	0.71718 (14)	0.21866 (9)	0.0214 (3)
O1	0.63114 (7)	0.99350 (11)	0.53105 (7)	0.0257 (3)
O2	0.66866 (7)	0.93655 (11)	0.29200 (7)	0.0217 (3)
H1	0.7381 (11)	0.6294 (17)	0.2210 (11)	0.038 (5)*
H2	0.4879 (11)	0.8765 (18)	0.4542 (10)	0.039 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0210 (8)	0.0190 (8)	0.0193 (9)	−0.0014 (7)	0.0050 (6)	0.0005 (7)
C2	0.0172 (8)	0.0152 (8)	0.0215 (9)	−0.0017 (7)	0.0023 (6)	0.0018 (7)
C3	0.0184 (7)	0.0108 (7)	0.0214 (8)	−0.0035 (6)	0.0021 (6)	−0.0015 (6)
C4	0.0178 (8)	0.0110 (7)	0.0197 (8)	−0.0028 (6)	0.0009 (6)	0.0006 (7)
C5	0.0210 (8)	0.0172 (8)	0.0210 (9)	−0.0002 (7)	0.0043 (6)	−0.0024 (7)
C6	0.0191 (8)	0.0187 (8)	0.0305 (10)	0.0035 (7)	−0.0017 (7)	0.0004 (7)
C7	0.0258 (8)	0.0215 (8)	0.0233 (9)	−0.0006 (7)	−0.0052 (7)	0.0030 (7)
C8	0.0260 (8)	0.0222 (8)	0.0168 (8)	−0.0028 (7)	0.0026 (6)	−0.0006 (7)
C9	0.0184 (8)	0.0221 (9)	0.0262 (9)	0.0009 (7)	0.0017 (7)	0.0001 (7)
C10	0.0181 (8)	0.0267 (9)	0.0197 (9)	−0.0052 (7)	0.0038 (6)	−0.0024 (7)
C11	0.0228 (9)	0.0406 (10)	0.0264 (10)	−0.0045 (8)	−0.0005 (7)	−0.0008 (8)
C12	0.0292 (10)	0.0578 (13)	0.0284 (11)	−0.0181 (10)	0.0031 (8)	−0.0149 (10)
C13	0.0406 (11)	0.0358 (11)	0.0339 (11)	−0.0211 (9)	0.0180 (8)	−0.0213 (9)
C14	0.0332 (10)	0.0252 (9)	0.0343 (10)	−0.0042 (8)	0.0161 (8)	−0.0049 (8)
C15	0.0219 (8)	0.0259 (9)	0.0235 (9)	−0.0045 (7)	0.0056 (7)	−0.0009 (8)
C16	0.0262 (9)	0.0204 (8)	0.0197 (9)	0.0081 (7)	−0.0045 (7)	−0.0010 (7)
C17	0.0368 (10)	0.0280 (9)	0.0326 (10)	0.0038 (8)	−0.0088 (8)	−0.0045 (8)
C18	0.0387 (10)	0.0294 (9)	0.0253 (10)	0.0072 (8)	0.0010 (7)	0.0025 (8)
F1	0.0638 (7)	0.0548 (7)	0.0630 (8)	−0.0279 (6)	0.0211 (6)	−0.0401 (6)
N1	0.0160 (7)	0.0170 (7)	0.0283 (8)	0.0009 (6)	0.0017 (6)	−0.0049 (6)
N2	0.0213 (7)	0.0164 (6)	0.0211 (7)	−0.0029 (6)	0.0028 (5)	−0.0033 (6)
N3	0.0283 (8)	0.0166 (7)	0.0192 (7)	0.0067 (6)	−0.0036 (6)	−0.0018 (6)
O1	0.0229 (6)	0.0202 (6)	0.0340 (7)	−0.0007 (5)	0.0037 (5)	−0.0103 (5)
O2	0.0267 (6)	0.0135 (5)	0.0247 (6)	0.0028 (5)	0.0004 (5)	0.0015 (5)

Geometric parameters (Å, º) top

C1—O1	1.2455 (16)	C11—H11	0.9500
C1—N1	1.3438 (18)	C12—C13	1.363 (2)
C1—C3	1.5022 (19)	C12—H12	0.9500
C2—O2	1.2476 (16)	C13—F1	1.3656 (18)
C2—N3	1.3330 (18)	C13—C14	1.375 (2)
C2—C4	1.500 (2)	C14—C15	1.385 (2)
C3—C8	1.3879 (19)	C14—H14	0.9500
C3—C4	1.3964 (19)	C15—H15	0.9500
C4—C5	1.3934 (18)	C16—N3	1.4658 (18)
C5—C6	1.3836 (19)	C16—C17	1.521 (2)
C5—H5	0.9500	C16—C18	1.5247 (19)
C6—C7	1.380 (2)	C16—H16	1.0000
C6—H6	0.9500	C17—H17A	0.9800
C7—C8	1.3831 (18)	C17—H17B	0.9800
C7—H7	0.9500	C17—H17C	0.9800
C8—H8	0.9500	C18—H18A	0.9800
C9—N2	1.2786 (17)	C18—H18B	0.9800
C9—C10	1.464 (2)	C18—H18C	0.9800
C9—H9	0.9500	N1—N2	1.3796 (16)
C10—C15	1.393 (2)	N1—H2	0.850 (15)
C10—C11	1.3972 (19)	N3—H1	0.875 (15)
C11—C12	1.386 (2)

O1—C1—N1	120.58 (13)	C11—C12—H12	121.1
O1—C1—C3	119.65 (13)	C12—C13—F1	118.60 (17)
N1—C1—C3	119.72 (13)	C12—C13—C14	123.75 (16)
O2—C2—N3	123.63 (14)	F1—C13—C14	117.65 (18)
O2—C2—C4	119.68 (13)	C13—C14—C15	117.74 (17)
N3—C2—C4	116.68 (13)	C13—C14—H14	121.1
C8—C3—C4	119.79 (13)	C15—C14—H14	121.1
C8—C3—C1	116.84 (13)	C14—C15—C10	121.07 (15)
C4—C3—C1	123.16 (13)	C14—C15—H15	119.5
C5—C4—C3	118.82 (13)	C10—C15—H15	119.5
C5—C4—C2	120.26 (13)	N3—C16—C17	109.39 (12)
C3—C4—C2	120.64 (12)	N3—C16—C18	110.32 (12)
C6—C5—C4	120.86 (14)	C17—C16—C18	111.86 (13)
C6—C5—H5	119.6	N3—C16—H16	108.4
C4—C5—H5	119.6	C17—C16—H16	108.4
C7—C6—C5	120.02 (14)	C18—C16—H16	108.4
C7—C6—H6	120.0	C16—C17—H17A	109.5
C5—C6—H6	120.0	C16—C17—H17B	109.5
C6—C7—C8	119.69 (14)	H17A—C17—H17B	109.5
C6—C7—H7	120.2	C16—C17—H17C	109.5
C8—C7—H7	120.2	H17A—C17—H17C	109.5
C7—C8—C3	120.76 (13)	H17B—C17—H17C	109.5
C7—C8—H8	119.6	C16—C18—H18A	109.5
C3—C8—H8	119.6	C16—C18—H18B	109.5
N2—C9—C10	120.58 (14)	H18A—C18—H18B	109.5
N2—C9—H9	119.7	C16—C18—H18C	109.5
C10—C9—H9	119.7	H18A—C18—H18C	109.5
C15—C10—C11	118.54 (15)	H18B—C18—H18C	109.5
C15—C10—C9	121.96 (14)	C1—N1—N2	121.06 (13)
C11—C10—C9	119.49 (14)	C1—N1—H2	118.7 (11)
C12—C11—C10	121.04 (16)	N2—N1—H2	120.2 (11)
C12—C11—H11	119.5	C9—N2—N1	114.89 (12)
C10—C11—H11	119.5	C2—N3—C16	122.92 (13)
C13—C12—C11	117.83 (16)	C2—N3—H1	121.8 (10)
C13—C12—H12	121.1	C16—N3—H1	115.3 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···O2ⁱ	0.875 (15)	2.127 (15)	2.9887 (16)	168.4 (14)
N1—H2···O1ⁱⁱ	0.850 (15)	1.976 (15)	2.8256 (16)	177.8 (15)

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈FN₃O₂
M_r	327.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	123
a, b, c (Å)	13.316 (3), 8.8904 (18), 14.102 (3)
β (°)	91.10 (3)
V (Å³)	1669.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.30 × 0.30

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi,1995)
T_min, T_max	0.944, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	15335, 3833, 2302
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.069, 1.02
No. of reflections	3833
No. of parameters	228
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.23

Computer programs: RAPID-AUTO (Rigaku, 2000), CrystalStructure (Molecular Structure Corporation and Rigaku, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···O2ⁱ	0.875 (15)	2.127 (15)	2.9887 (16)	168.4 (14)
N1—H2···O1ⁱⁱ	0.850 (15)	1.976 (15)	2.8256 (16)	177.8 (15)

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) −x+1, −y+2, −z+1.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (NNSFC) (grant No. 20572129), National Basic Research Program of China (2003CB114405) and National Key Project of Scientific and Technical Supporting Programs Funded by Ministry of Science & Technology of China (No. 2006BAE01AE01–11).

References

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