N′-tert-Butyl-5-(4-chloro­phen­yl)furan-2-carbohydrazide

Li, X.-C.; Li, Y.; Cui, Z.-N.; Yang, X.-L.; Ling, Y.

doi:10.1107/S1600536808003486

organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o561

doi:10.1107/S1600536808003486

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N′-tert-Butyl-5-(4-chlorophenyl)furan-2-carbohydrazide

Xi-Chen Li,^a Ying Li,^a Zi-Ning Cui,^a Xin-Ling Yang ^a and Yun Ling ^a ^*

^aDepartment of Applied Chemistry, College of Science, China Agricultural University, Key Laboratory of Pesticide Chemistry and Application Technology, Ministry of Agriculture, Beijing 100094, People's Republic of China
^*Correspondence e-mail: lyun@cau.edu.cn

(Received 26 December 2007; accepted 31 January 2008; online 6 February 2008)

In the title molecule, C₁₅H₁₇ClN₂O₂, the furan and benzene rings form a dihedral angle of 15.35 (8)°. In the crystal structure, intermolecular N—H⋯O hydrogen bonds link the molecules into chains extended in the [010] direction.

Related literature

For general background, see: Wing (1988 ); Wing et al. (1988 ); Dhadialla et al. (1998 ); Heller et al. (1992 ); Mao et al. (2004 ). For details of some monoacylhydrazines and diacylhydrazines containing furan, see: Yang et al. (2002 ); Li et al. (2006 ).

Experimental

Crystal data

C₁₅H₁₇ClN₂O₂
M_r = 292.76
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.3770 (7) Å
b = 9.7861 (7) Å
c = 16.0119 (12) Å
V = 1469.32 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 113 (2) K
0.32 × 0.24 × 0.20 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.921, T_max = 0.949
13814 measured reflections
3496 independent reflections
2754 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.056
S = 0.96
3496 reflections
192 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 1490 Friedel pairs
Flack parameter: 0.00 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ⁱ	0.882 (15)	2.026 (16)	2.8744 (15)	160.9 (14)
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku/MSC, 2005).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808003486/cv2380sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808003486/cv2380Isup2.hkl

checkCIF report

Comment top

As one of molting hormone analogs, symmetrical N'-tert-butyl-N,N'-dibenzoylhydrazine (RH-5849) was first found to be a nonsteroidal ecdysone agonist in 1988 (Wing, 1988; Wing et al., 1988). Afterward, several diacylhydrazine compounds were commercially developed as insect growth regulators (IGRs) which were widely used in agriculture (Dhadialla et al., 1998; Heller et al., 1992; Mao et al., 2004). Recently, we synthesized a series of di- or mono- acylhydrazines containing furan for further study on the structure-activity relationship between monoacylhydrazines and diacylhydrazines. It was found that they both had good insecticidal activities (Yang et al., 2002; Li et al., 2006). In order to study the structural character and conformation of the monoacylhydrazine containing furan, the crystal structure of the title compound, (I), has been determined.

In (I) (Fig. 1), the benzene (C1—C6) and furan (O1/C7—C10) rings form a dihedral angle of 15.35 (8)°. The carbonyl group attached to the furan ring is almost coplanar with it. In the crystal, the intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into chains extended in direction [010].

Related literature top

For general background, see: Wing (1988); Wing et al. (1988); Dhadialla et al. (1998); Heller et al. (1992); Mao et al. (2004). For details of some monoacylhydrazines and diacylhydrazines containing furan, see: Yang et al. (2002); Li et al. (2006).

Experimental top

The title compound, (I), was synthesized by the reaction of 5-(4-chlorophenyl)furan-2-carbonyl chloride (0.96 g, 4 mmol) with tert-butylhydrazine hydrochloride (1.99 g, 16 mmol) using sodium hydroxide (10%, 8.0 g, 20 mmol) as the acid-binding agent. The mixture was stirred at room temperature for 5 h and filtered to obtain a yellow solution. Then the organic phase was separated and dried with anhydrous magnesium sulfate overnight. After removal of the solvent, the residue was purified by vacuum column chromatography on silica gel with petroleum ether and ethyl acetate as the eluent (V _{petroleum ether}: V _{ethyl acetate} = 3:1) and then recrystallized from hexane–ethyl acetate (V_hexane: V_{ethyl acetate}= 1:1) to give colourless crystals suitable for X-ray diffraction (Li et al., 2006).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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: CrystalStructure (Rigaku/MSC, 2005).

Figures top

Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.

N'-tert-Butyl-5-(4-chlorophenyl)furan-2-carbohydrazide top

Crystal data top

C₁₅H₁₇ClN₂O₂	D_x = 1.323 Mg m⁻³
M_r = 292.76	Mo Kα radiation, λ = 0.71070 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 3053 reflections
a = 9.3770 (7) Å	θ = 2.5–25.0°
b = 9.7861 (7) Å	µ = 0.26 mm⁻¹
c = 16.0119 (12) Å	T = 113 K
V = 1469.32 (19) Å³	Prism, colourless
Z = 4	0.32 × 0.24 × 0.20 mm
F(000) = 616

Data collection top

Rigaku Saturn diffractometer	3496 independent reflections
Radiation source: rotating anode	2754 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.039
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 2.4°
ω scans	h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −12→12
T_min = 0.921, T_max = 0.949	l = −21→21
13814 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)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.056	w = 1/[σ²(F_o²) + (0.0232P)²] where P = (F_o² + 2F_c²)/3
S = 0.96	(Δ/σ)_max = 0.001
3496 reflections	Δρ_max = 0.22 e Å⁻³
192 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1490 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (4)

Crystal data top

C₁₅H₁₇ClN₂O₂	V = 1469.32 (19) Å³
M_r = 292.76	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.3770 (7) Å	µ = 0.26 mm⁻¹
b = 9.7861 (7) Å	T = 113 K
c = 16.0119 (12) Å	0.32 × 0.24 × 0.20 mm

Data collection top

Rigaku Saturn diffractometer	3496 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	2754 reflections with I > 2σ(I)
T_min = 0.921, T_max = 0.949	R_int = 0.039
13814 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.056	Δρ_max = 0.22 e Å⁻³
S = 0.96	Δρ_min = −0.21 e Å⁻³
3496 reflections	Absolute structure: Flack (1983), 1490 Friedel pairs
192 parameters	Absolute structure parameter: 0.00 (4)
0 restraints

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
Cl1	1.32887 (4)	0.17773 (4)	1.09957 (2)	0.02303 (9)
O1	1.13067 (10)	0.70996 (9)	0.86903 (6)	0.0151 (2)
O2	0.98638 (10)	0.97666 (9)	0.74249 (6)	0.0174 (2)
N1	0.91782 (13)	0.75551 (12)	0.76336 (7)	0.0151 (3)
N2	0.80263 (13)	0.76074 (12)	0.70613 (7)	0.0146 (3)
C1	1.30520 (15)	0.33360 (15)	1.04901 (8)	0.0159 (3)
C2	1.17767 (16)	0.35872 (14)	1.00795 (8)	0.0168 (3)
H2	1.1040	0.2921	1.0078	0.020*
C3	1.15907 (16)	0.48241 (13)	0.96720 (8)	0.0159 (3)
H3	1.0720	0.5002	0.9389	0.019*
C4	1.26701 (15)	0.58168 (15)	0.96708 (9)	0.0149 (3)
C5	1.39448 (15)	0.55382 (14)	1.00941 (8)	0.0176 (3)
H5	1.4685	0.6201	1.0100	0.021*
C6	1.41381 (15)	0.43007 (14)	1.05056 (9)	0.0175 (3)
H6	1.5003	0.4117	1.0794	0.021*
C7	1.24400 (15)	0.71056 (14)	0.92346 (8)	0.0153 (3)
C8	1.30641 (15)	0.83596 (15)	0.92271 (8)	0.0175 (3)
H8	1.3868	0.8635	0.9547	0.021*
C9	1.22900 (14)	0.91848 (15)	0.86505 (9)	0.0165 (3)
H9	1.2472	1.0113	0.8515	0.020*
C10	1.12421 (14)	0.83819 (14)	0.83345 (8)	0.0137 (3)
C11	1.00485 (15)	0.86322 (14)	0.77523 (8)	0.0138 (3)
C12	0.66234 (15)	0.78352 (14)	0.74892 (9)	0.0163 (3)
C13	0.65461 (17)	0.92221 (15)	0.79274 (9)	0.0240 (4)
H13A	0.7283	0.9270	0.8360	0.036*
H13B	0.5604	0.9333	0.8184	0.036*
H13C	0.6701	0.9952	0.7518	0.036*
C14	0.55159 (16)	0.77717 (16)	0.67895 (10)	0.0241 (4)
H14A	0.5713	0.8491	0.6380	0.036*
H14B	0.4561	0.7906	0.7025	0.036*
H14C	0.5563	0.6877	0.6516	0.036*
C15	0.63850 (16)	0.66767 (15)	0.81165 (9)	0.0230 (3)
H15A	0.6501	0.5795	0.7834	0.035*
H15B	0.5419	0.6742	0.8347	0.035*
H15C	0.7083	0.6751	0.8570	0.035*
H2A	0.8186 (15)	0.8364 (13)	0.6731 (8)	0.012 (4)*
H1A	0.9484 (16)	0.6722 (16)	0.7743 (9)	0.029 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.02355 (19)	0.02007 (19)	0.0255 (2)	0.00437 (17)	−0.00042 (17)	0.00723 (17)
O1	0.0162 (5)	0.0122 (5)	0.0169 (5)	0.0000 (4)	−0.0040 (4)	0.0010 (4)
O2	0.0205 (5)	0.0104 (5)	0.0214 (5)	−0.0001 (4)	−0.0019 (5)	0.0019 (4)
N1	0.0154 (6)	0.0107 (7)	0.0192 (7)	0.0012 (5)	−0.0047 (5)	0.0004 (5)
N2	0.0145 (7)	0.0146 (7)	0.0146 (6)	0.0003 (5)	−0.0032 (5)	0.0022 (5)
C1	0.0218 (8)	0.0154 (7)	0.0105 (7)	0.0048 (7)	0.0022 (6)	0.0016 (6)
C2	0.0168 (7)	0.0180 (8)	0.0157 (7)	−0.0019 (6)	0.0012 (7)	−0.0011 (6)
C3	0.0146 (7)	0.0187 (8)	0.0144 (7)	0.0016 (6)	−0.0031 (6)	−0.0010 (6)
C4	0.0157 (7)	0.0162 (8)	0.0128 (7)	0.0021 (6)	−0.0004 (6)	−0.0034 (6)
C5	0.0180 (8)	0.0172 (8)	0.0177 (8)	−0.0014 (6)	−0.0022 (6)	−0.0043 (6)
C6	0.0157 (8)	0.0225 (8)	0.0144 (8)	0.0045 (7)	−0.0029 (6)	−0.0021 (6)
C7	0.0125 (7)	0.0185 (8)	0.0150 (8)	0.0015 (6)	−0.0024 (6)	−0.0025 (6)
C8	0.0137 (7)	0.0185 (7)	0.0202 (8)	−0.0026 (6)	−0.0021 (6)	−0.0018 (6)
C9	0.0169 (7)	0.0129 (7)	0.0196 (8)	−0.0008 (6)	0.0022 (6)	0.0011 (6)
C10	0.0157 (7)	0.0106 (7)	0.0149 (7)	0.0023 (6)	0.0015 (6)	0.0004 (6)
C11	0.0139 (7)	0.0139 (8)	0.0137 (7)	0.0019 (6)	0.0041 (6)	−0.0023 (6)
C12	0.0134 (7)	0.0168 (7)	0.0187 (8)	0.0007 (6)	−0.0017 (7)	0.0000 (6)
C13	0.0207 (9)	0.0222 (8)	0.0292 (9)	0.0024 (7)	−0.0007 (7)	−0.0052 (7)
C14	0.0209 (8)	0.0245 (9)	0.0270 (9)	0.0008 (7)	−0.0075 (7)	0.0012 (7)
C15	0.0224 (8)	0.0230 (8)	0.0237 (8)	−0.0003 (8)	−0.0005 (7)	0.0029 (7)

Geometric parameters (Å, º) top

Cl1—C1	1.7411 (14)	C6—H6	0.9500
O1—C7	1.3744 (15)	C7—C8	1.360 (2)
O1—C10	1.3795 (16)	C8—C9	1.4252 (19)
O2—C11	1.2398 (15)	C8—H8	0.9500
N1—C11	1.3465 (17)	C9—C10	1.3561 (18)
N1—N2	1.4174 (16)	C9—H9	0.9500
N1—H1A	0.882 (15)	C10—C11	1.4771 (19)
N2—C12	1.4999 (18)	C12—C14	1.5289 (19)
N2—H2A	0.922 (13)	C12—C13	1.5296 (18)
C1—C2	1.3866 (19)	C12—C15	1.5311 (18)
C1—C6	1.3889 (19)	C13—H13A	0.9800
C2—C3	1.3861 (17)	C13—H13B	0.9800
C2—H2	0.9500	C13—H13C	0.9800
C3—C4	1.4029 (19)	C14—H14A	0.9800
C3—H3	0.9500	C14—H14B	0.9800
C4—C5	1.4009 (18)	C14—H14C	0.9800
C4—C7	1.4578 (19)	C15—H15A	0.9800
C5—C6	1.3906 (19)	C15—H15B	0.9800
C5—H5	0.9500	C15—H15C	0.9800

C7—O1—C10	106.97 (10)	C10—C9—H9	126.8
C11—N1—N2	121.66 (12)	C8—C9—H9	126.8
C11—N1—H1A	119.9 (10)	C9—C10—O1	109.95 (12)
N2—N1—H1A	114.2 (10)	C9—C10—C11	133.51 (13)
N1—N2—C12	112.24 (10)	O1—C10—C11	116.41 (12)
N1—N2—H2A	106.0 (9)	O2—C11—N1	123.82 (13)
C12—N2—H2A	106.6 (9)	O2—C11—C10	121.41 (13)
C2—C1—C6	121.36 (13)	N1—C11—C10	114.74 (12)
C2—C1—Cl1	119.06 (11)	N2—C12—C14	104.77 (11)
C6—C1—Cl1	119.58 (11)	N2—C12—C13	112.52 (12)
C3—C2—C1	119.11 (13)	C14—C12—C13	109.88 (12)
C3—C2—H2	120.4	N2—C12—C15	108.52 (11)
C1—C2—H2	120.4	C14—C12—C15	110.58 (12)
C2—C3—C4	120.97 (14)	C13—C12—C15	110.44 (12)
C2—C3—H3	119.5	C12—C13—H13A	109.5
C4—C3—H3	119.5	C12—C13—H13B	109.5
C5—C4—C3	118.69 (13)	H13A—C13—H13B	109.5
C5—C4—C7	121.77 (13)	C12—C13—H13C	109.5
C3—C4—C7	119.54 (13)	H13A—C13—H13C	109.5
C6—C5—C4	120.66 (13)	H13B—C13—H13C	109.5
C6—C5—H5	119.7	C12—C14—H14A	109.5
C4—C5—H5	119.7	C12—C14—H14B	109.5
C1—C6—C5	119.20 (13)	H14A—C14—H14B	109.5
C1—C6—H6	120.4	C12—C14—H14C	109.5
C5—C6—H6	120.4	H14A—C14—H14C	109.5
C8—C7—O1	109.33 (12)	H14B—C14—H14C	109.5
C8—C7—C4	136.18 (13)	C12—C15—H15A	109.5
O1—C7—C4	114.49 (12)	C12—C15—H15B	109.5
C7—C8—C9	107.33 (13)	H15A—C15—H15B	109.5
C7—C8—H8	126.3	C12—C15—H15C	109.5
C9—C8—H8	126.3	H15A—C15—H15C	109.5
C10—C9—C8	106.41 (13)	H15B—C15—H15C	109.5

C11—N1—N2—C12	−101.13 (14)	O1—C7—C8—C9	−0.05 (16)
C6—C1—C2—C3	0.5 (2)	C4—C7—C8—C9	−179.46 (15)
Cl1—C1—C2—C3	−179.57 (10)	C7—C8—C9—C10	−0.42 (16)
C1—C2—C3—C4	0.0 (2)	C8—C9—C10—O1	0.73 (16)
C2—C3—C4—C5	−0.3 (2)	C8—C9—C10—C11	176.25 (14)
C2—C3—C4—C7	179.88 (13)	C7—O1—C10—C9	−0.77 (15)
C3—C4—C5—C6	0.2 (2)	C7—O1—C10—C11	−177.14 (11)
C7—C4—C5—C6	180.00 (13)	N2—N1—C11—O2	5.2 (2)
C2—C1—C6—C5	−0.6 (2)	N2—N1—C11—C10	−176.72 (11)
Cl1—C1—C6—C5	179.45 (10)	C9—C10—C11—O2	1.9 (2)
C4—C5—C6—C1	0.3 (2)	O1—C10—C11—O2	177.18 (12)
C10—O1—C7—C8	0.49 (14)	C9—C10—C11—N1	−176.21 (15)
C10—O1—C7—C4	−179.95 (11)	O1—C10—C11—N1	−0.92 (17)
C5—C4—C7—C8	−15.6 (3)	N1—N2—C12—C14	−176.55 (11)
C3—C4—C7—C8	164.26 (16)	N1—N2—C12—C13	64.11 (15)
C5—C4—C7—O1	165.04 (12)	N1—N2—C12—C15	−58.41 (14)
C3—C4—C7—O1	−15.13 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.882 (15)	2.026 (16)	2.8744 (15)	160.9 (14)

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₇ClN₂O₂
M_r	292.76
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	113
a, b, c (Å)	9.3770 (7), 9.7861 (7), 16.0119 (12)
V (Å³)	1469.32 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.32 × 0.24 × 0.20

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.921, 0.949
No. of measured, independent and observed [I > 2σ(I)] reflections	13814, 3496, 2754
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.056, 0.96
No. of reflections	3496
No. of parameters	192
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.21
Absolute structure	Flack (1983), 1490 Friedel pairs
Absolute structure parameter	0.00 (4)

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku/MSC, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.882 (15)	2.026 (16)	2.8744 (15)	160.9 (14)

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

Acknowledgements

This work was supported by the National Basic Research Programme of China (grant No. 2003CB114405), the National Natural Science Foundation of China (grant No. 20672138) and the National High Technology Research and Development Programme of China (grant No. 2006AA10A201). The authors also thank the State Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin, People's Republic of China.

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