(E)-N'-(2-Fluoro-benzyl-idene)furan-2-carbohydrazide.

The title compound, C(12)H(9)FN(2)O(2), was prepared by the reaction of 2-fluoro-benzaldehyde 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, mol-ecules 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 = 232.21

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.158

S = 1.12

2597 reflections

200 parameters

39 restraints

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

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.

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

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

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

C12H9FN2O2	F(000) = 480
Mr = 232.21	Dx = 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

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

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(Fo2) + (0.0717P)2 + 0.0765P] where P = (Fo2 + 2Fc2)/3
2597 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.18 e Å−3
39 restraints	Δρmin = −0.20 e Å−3

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	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)

	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)

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)

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.

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) .