(E)-N′-(2-Fluoro­benzyl­idene)furan-2-carbohydrazide

Jiang, J.-H.

doi:10.1107/S1600536810052980

organic compounds

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Volume 67| Part 2| February 2011| Page o240

doi:10.1107/S1600536810052980

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(E)-N′-(2-Fluorobenzylidene)furan-2-carbohydrazide

Jin-He Jiang ^a ^*

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: weifangjjh@126.com

(Received 5 December 2010; accepted 17 December 2010; online 8 January 2011)

The title compound, C₁₂H₉FN₂O₂, was prepared by the reaction of 2-fluorobenzaldehyde and furan-2-carbohydrazide. The furan ring is disordered over two sets of sites with refined occupancies of 0.60 (3):0.40 (3). The major and minor components of the furan ring make dihedral angles of 51.9 (6) and 38.0 (10)°, respectively, with the benzene ring. In the crystal, molecules are linked via bifurcated N—H⋯O(N) hydrogen bonds into chains along [001].

Related literature

For related structures, see: Li & Jian (2010 ); Li & Meng (2010 ).

Experimental

Crystal data

C₁₂H₉FN₂O₂
M_r = 232.21
Monoclinic, P 2₁ /c
a = 11.719 (2) Å
b = 13.395 (3) Å
c = 7.5154 (15) Å
β = 105.04 (3)°
V = 1139.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.23 × 0.19 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
10898 measured reflections
2597 independent reflections
1341 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.158
S = 1.12
2597 reflections
200 parameters
39 restraints
H-atom parameters constrained
Δρ_max = 0.18 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⋯O2ⁱ	0.86	2.13	2.956 (2)	162
N1—H1⋯N2ⁱ	0.86	2.63	3.216 (3)	127
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810052980/lh5184sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810052980/lh5184Isup2.hkl

checkCIF report

Comment top

The molecular structure of the title compound is shown in Fig. 1. The bond lengths and angles in the carbohydrazide group of the title compound can be compared with two examples of thiosemicarbazides recently published (Li & Jian, 2010; Li & Meng,2010). In the title molecule, the furan ring is disordered over two sets of sites with refined occupancies of 0.60 (3):0.40 (3). The diherdal angles that the major and minor components of the furan ring make with the benzene ring are 51.9 (6) and 38.0 (10)°, respectively. In the crystal, molecules are linked via bifurcated N—H···O(N) hydrogen bonds to form one-dimensional chains along [001].

Related literature top

For related structures, see: Li & Jian (2010); Li & Meng (2010).

Experimental top

A mixture of 2-fluorobenzaldehyde (0.01 mol) and furan-2-carbohydrazide (0.01 mol) was stirred in refluxing ethanol (20 mL) for 2h to afford the title compound (0.087 mol, yield 87%). Single crystals suitable for X-ray measurements were obtained by recrystallization of a solution of the title compound in ethanol at room temperature.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids and the atom-numbering scheme. The disorder is not shown.

(E)-N'-(2-Fluorobenzylidene)furan-2-carbohydrazide top

Crystal data top

C₁₂H₉FN₂O₂	F(000) = 480
M_r = 232.21	D_x = 1.354 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2597 reflections
a = 11.719 (2) Å	θ = 3.0–27.5°
b = 13.395 (3) Å	µ = 0.11 mm⁻¹
c = 7.5154 (15) Å	T = 293 K
β = 105.04 (3)°	Bar, colorless
V = 1139.3 (4) Å³	0.23 × 0.19 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	1341 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.040
Graphite monochromator	θ_max = 27.5°, θ_min = 3.0°
ϕ and ω scans	h = −15→15
10898 measured reflections	k = −15→17
2597 independent reflections	l = −9→9

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.158	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0717P)² + 0.0765P] where P = (F_o² + 2F_c²)/3
2597 reflections	(Δ/σ)_max < 0.001
200 parameters	Δρ_max = 0.18 e Å⁻³
39 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₂H₉FN₂O₂	V = 1139.3 (4) Å³
M_r = 232.21	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.719 (2) Å	µ = 0.11 mm⁻¹
b = 13.395 (3) Å	T = 293 K
c = 7.5154 (15) Å	0.23 × 0.19 × 0.18 mm
β = 105.04 (3)°

Data collection top

Bruker SMART CCD diffractometer	1341 reflections with I > 2σ(I)
10898 measured reflections	R_int = 0.040
2597 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	39 restraints
wR(F²) = 0.158	H-atom parameters constrained
S = 1.12	Δρ_max = 0.18 e Å⁻³
2597 reflections	Δρ_min = −0.20 e Å⁻³
200 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	Occ. (<1)
F1	0.43175 (12)	0.53700 (8)	0.31687 (19)	0.0719 (5)
O1	0.0418 (10)	0.1625 (9)	0.4392 (11)	0.081 (2)	0.60 (3)
C1	−0.0584 (13)	0.1286 (11)	0.4755 (19)	0.115 (5)	0.60 (3)
H1A	−0.0803	0.1413	0.5837	0.138*	0.60 (3)
C2	−0.1205 (12)	0.0754 (13)	0.338 (2)	0.106 (5)	0.60 (3)
H2A	−0.1905	0.0417	0.3340	0.128*	0.60 (3)
C3	−0.0611 (9)	0.0790 (11)	0.1994 (16)	0.094 (4)	0.60 (3)
H3A	−0.0861	0.0508	0.0826	0.112*	0.60 (3)
C4	0.0386 (10)	0.1308 (12)	0.2665 (16)	0.049 (3)	0.60 (3)
C5	0.13101 (18)	0.16408 (13)	0.1818 (3)	0.0467 (5)
O1A	0.0064 (15)	0.1954 (17)	0.388 (3)	0.091 (4)	0.40 (3)
C1A	−0.0962 (19)	0.161 (2)	0.414 (4)	0.136 (9)	0.40 (3)
H1AA	−0.1274	0.1796	0.5112	0.163*	0.40 (3)
C2A	−0.1460 (15)	0.097 (2)	0.286 (3)	0.109 (7)	0.40 (3)
H2AA	−0.2194	0.0666	0.2704	0.131*	0.40 (3)
C3A	−0.0675 (10)	0.0831 (13)	0.176 (2)	0.080 (4)	0.40 (3)
H3AA	−0.0755	0.0378	0.0800	0.096*	0.40 (3)
C4A	0.0216 (14)	0.1477 (18)	0.236 (3)	0.051 (4)	0.40 (3)
O2	0.14506 (13)	0.12419 (9)	0.04193 (19)	0.0578 (4)
N1	0.20365 (15)	0.23571 (11)	0.2747 (2)	0.0485 (4)
H1	0.1890	0.2647	0.3684	0.058*
N2	0.30170 (15)	0.26118 (11)	0.2161 (2)	0.0473 (4)
C6	0.35441 (18)	0.34096 (13)	0.2850 (3)	0.0476 (5)
H6A	0.3232	0.3800	0.3633	0.057*
C7	0.46353 (18)	0.37102 (13)	0.2411 (3)	0.0473 (5)
C8	0.5360 (2)	0.30396 (16)	0.1816 (3)	0.0646 (6)
H8A	0.5138	0.2373	0.1648	0.078*
C9	0.6401 (2)	0.33467 (18)	0.1471 (4)	0.0802 (8)
H9A	0.6872	0.2890	0.1057	0.096*
C10	0.6750 (2)	0.43347 (19)	0.1738 (4)	0.0784 (8)
H10A	0.7464	0.4537	0.1528	0.094*
C11	0.6051 (2)	0.50132 (18)	0.2309 (3)	0.0654 (7)
H11A	0.6275	0.5680	0.2481	0.078*
C12	0.50190 (19)	0.46913 (14)	0.2619 (3)	0.0521 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0725 (10)	0.0524 (7)	0.0988 (10)	−0.0030 (6)	0.0365 (8)	−0.0100 (6)
O1	0.089 (4)	0.101 (4)	0.067 (3)	−0.054 (3)	0.044 (3)	−0.025 (3)
C1	0.126 (7)	0.143 (7)	0.106 (6)	−0.090 (7)	0.083 (6)	−0.054 (6)
C2	0.101 (7)	0.124 (8)	0.116 (6)	−0.073 (8)	0.068 (6)	−0.047 (6)
C3	0.080 (6)	0.124 (8)	0.088 (4)	−0.057 (6)	0.042 (4)	−0.043 (5)
C4	0.049 (3)	0.049 (4)	0.054 (3)	−0.009 (4)	0.020 (3)	−0.003 (4)
C5	0.0477 (11)	0.0443 (10)	0.0512 (11)	−0.0034 (8)	0.0184 (9)	−0.0013 (9)
O1A	0.074 (6)	0.124 (8)	0.092 (6)	−0.043 (6)	0.054 (6)	−0.043 (6)
C1A	0.089 (9)	0.182 (17)	0.170 (15)	−0.061 (10)	0.094 (11)	−0.076 (13)
C2A	0.055 (6)	0.116 (10)	0.170 (16)	−0.031 (6)	0.054 (8)	−0.036 (10)
C3A	0.058 (6)	0.060 (7)	0.129 (9)	−0.019 (5)	0.036 (6)	−0.028 (6)
C4A	0.044 (4)	0.051 (7)	0.060 (6)	−0.007 (5)	0.017 (5)	−0.003 (6)
C5A	0.0477 (11)	0.0443 (10)	0.0512 (11)	−0.0034 (8)	0.0184 (9)	−0.0013 (9)
O2	0.0627 (11)	0.0534 (8)	0.0635 (10)	−0.0095 (7)	0.0273 (8)	−0.0141 (7)
N1	0.0484 (11)	0.0552 (9)	0.0479 (9)	−0.0149 (7)	0.0232 (8)	−0.0077 (7)
N2	0.0439 (10)	0.0513 (9)	0.0506 (9)	−0.0080 (7)	0.0193 (8)	−0.0005 (7)
C6	0.0486 (13)	0.0471 (10)	0.0512 (12)	−0.0050 (9)	0.0203 (10)	−0.0020 (8)
C7	0.0460 (12)	0.0492 (10)	0.0495 (12)	−0.0070 (8)	0.0173 (10)	−0.0012 (8)
C8	0.0607 (15)	0.0562 (12)	0.0855 (17)	−0.0086 (11)	0.0343 (13)	−0.0112 (11)
C9	0.0643 (17)	0.0822 (16)	0.108 (2)	−0.0072 (13)	0.0475 (16)	−0.0231 (15)
C10	0.0602 (17)	0.0895 (17)	0.0962 (19)	−0.0231 (13)	0.0397 (15)	−0.0146 (14)
C11	0.0638 (16)	0.0630 (13)	0.0750 (16)	−0.0211 (11)	0.0281 (13)	−0.0075 (11)
C12	0.0526 (14)	0.0514 (11)	0.0559 (12)	−0.0053 (9)	0.0207 (11)	−0.0051 (9)

Geometric parameters (Å, º) top

F1—C12	1.360 (2)	C3A—C4A	1.341 (4)
O1—C1	1.351 (4)	C3A—H3AA	0.9300
O1—C4	1.357 (4)	N1—N2	1.376 (2)
C1—C2	1.308 (5)	N1—H1	0.8600
C1—H1A	0.9300	N2—C6	1.275 (2)
C2—C3	1.397 (6)	C6—C7	1.458 (3)
C2—H2A	0.9300	C6—H6A	0.9300
C3—C4	1.340 (4)	C7—C12	1.385 (3)
C3—H3A	0.9300	C7—C8	1.387 (3)
C4—C5	1.461 (4)	C8—C9	1.375 (3)
C5—O2	1.228 (2)	C8—H8A	0.9300
C5—N1	1.351 (2)	C9—C10	1.384 (3)
O1A—C1A	1.351 (4)	C9—H9A	0.9300
O1A—C4A	1.357 (4)	C10—C11	1.365 (3)
C1A—C2A	1.308 (6)	C10—H10A	0.9300
C1A—H1AA	0.9300	C11—C12	1.360 (3)
C2A—C3A	1.397 (6)	C11—H11A	0.9300
C2A—H2AA	0.9300

C1—O1—C4	106.1 (3)	C3A—C4A—O1A	109.1 (3)
C2—C1—O1	111.0 (3)	C5—N1—N2	118.48 (16)
C2—C1—H1A	124.5	C5—N1—H1	120.8
O1—C1—H1A	124.5	N2—N1—H1	120.8
C1—C2—C3	106.7 (3)	C6—N2—N1	115.75 (16)
C1—C2—H2A	126.7	N2—C6—C7	120.04 (17)
C3—C2—H2A	126.7	N2—C6—H6A	120.0
C4—C3—C2	106.9 (4)	C7—C6—H6A	120.0
C4—C3—H3A	126.5	C12—C7—C8	116.29 (19)
C2—C3—H3A	126.5	C12—C7—C6	120.98 (17)
C3—C4—O1	109.1 (3)	C8—C7—C6	122.70 (17)
C3—C4—C5	131.8 (5)	C9—C8—C7	121.0 (2)
O1—C4—C5	118.8 (2)	C9—C8—H8A	119.5
O2—C5—N1	123.05 (18)	C7—C8—H8A	119.5
O2—C5—C4	121.3 (3)	C8—C9—C10	120.1 (2)
N1—C5—C4	115.5 (2)	C8—C9—H9A	119.9
C1A—O1A—C4A	106.1 (3)	C10—C9—H9A	119.9
C2A—C1A—O1A	111.1 (3)	C11—C10—C9	120.2 (2)
C2A—C1A—H1AA	124.5	C11—C10—H10A	119.9
O1A—C1A—H1AA	124.5	C9—C10—H10A	119.9
C1A—C2A—C3A	106.6 (3)	C12—C11—C10	118.4 (2)
C1A—C2A—H2AA	126.7	C12—C11—H11A	120.8
C3A—C2A—H2AA	126.7	C10—C11—H11A	120.8
C4A—C3A—C2A	106.8 (4)	C11—C12—F1	118.34 (18)
C4A—C3A—H3AA	126.6	C11—C12—C7	123.97 (19)
C2A—C3A—H3AA	126.6	F1—C12—C7	117.69 (17)

C4—O1—C1—C2	2.1 (18)	C4—C5—N1—N2	171.6 (9)
O1—C1—C2—C3	−3 (2)	C5—N1—N2—C6	167.22 (18)
C1—C2—C3—C4	3 (2)	N1—N2—C6—C7	176.02 (17)
C2—C3—C4—O1	−2 (2)	N2—C6—C7—C12	158.9 (2)
C2—C3—C4—C5	−175.4 (17)	N2—C6—C7—C8	−22.8 (3)
C1—O1—C4—C3	0.1 (18)	C12—C7—C8—C9	0.4 (4)
C1—O1—C4—C5	174.4 (13)	C6—C7—C8—C9	−177.9 (2)
C3—C4—C5—O2	−21 (3)	C7—C8—C9—C10	0.9 (4)
O1—C4—C5—O2	166.6 (10)	C8—C9—C10—C11	−1.4 (4)
C3—C4—C5—N1	163.9 (18)	C9—C10—C11—C12	0.6 (4)
O1—C4—C5—N1	−8.8 (17)	C10—C11—C12—F1	−179.3 (2)
C4A—O1A—C1A—C2A	−2 (3)	C10—C11—C12—C7	0.7 (4)
O1A—C1A—C2A—C3A	5 (3)	C8—C7—C12—C11	−1.2 (3)
C1A—C2A—C3A—C4A	−6 (3)	C6—C7—C12—C11	177.1 (2)
C2A—C3A—C4A—O1A	5 (3)	C8—C7—C12—F1	178.85 (19)
C1A—O1A—C4A—C3A	−2 (3)	C6—C7—C12—F1	−2.8 (3)
O2—C5—N1—N2	−3.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	2.13	2.956 (2)	162
N1—H1···N2ⁱ	0.86	2.63	3.216 (3)	127

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₉FN₂O₂
M_r	232.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.719 (2), 13.395 (3), 7.5154 (15)
β (°)	105.04 (3)
V (Å³)	1139.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.23 × 0.19 × 0.18

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10898, 2597, 1341
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.158, 1.12
No. of reflections	2597
No. of parameters	200
No. of restraints	39
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.20

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), 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
N1—H1···O2ⁱ	0.86	2.13	2.956 (2)	161.7
N1—H1···N2ⁱ	0.86	2.63	3.216 (3)	126.8

Symmetry code: (i) x, −y+1/2, z+1/2.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, Y.-F. & Jian, F.-F. (2010). Acta Cryst. E66, o1399. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, Y.-F. & Meng, F.-Y. (2010). Acta Cryst. E66, o2685. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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doi:10.1107/S1600536810052980

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