2-(4-Fluoro-benzyl-idene)propane-dinitrile: monoclinic polymorph.

The title compound, C10H5FN2, is a monoclinic (P21/c) polymorph of the previously reported triclinic (P-1) form [Anti-pin et al. (2003 ▶). J. Mol. Struct. 650, 1-20]. The 13 non-H atoms in the title polymorph are almost coplanar (r.m.s. deviation = 0.020 Å); a small twist between the fluoro-benzene and dinitrile groups [C-C-C-C torsion angle = 175.49 (16)°] is evident in the triclinic polymorph. In the crystal, C-H⋯N inter-actions lead to supra-molecular layers parallel to (-101); these are connected by C-F⋯π inter-actions.

Related literature

For background to the chemistry and biological activity of 4H-pyran derivatives, see: El-Agrody et al. (2011 ▶); Sabry et al. (2011 ▶). For the structure of the triclinic polymorph, see: Anti­pin et al. (2003 ▶); Ng & Tiekink (2013 ▶).

Experimental

Crystal data

C10H5FN2

M = 172.16

Monoclinic,

a = 9.1491 (9) Å

b = 12.7961 (14) Å

c = 7.5828 (11) Å

β = 106.317 (13)°

V = 851.98 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 295 K

0.35 × 0.15 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.892, T max = 1.000

7732 measured reflections

1957 independent reflections

1149 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.190

S = 1.09

1957 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶), QMol (Gans & Shalloway, 2001 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813006235/hb7051sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813006235/hb7051Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813006235/hb7051Isup3.cml

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

C10H5FN2	F(000) = 352
Mr = 172.16	Dx = 1.342 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1835 reflections
a = 9.1491 (9) Å	θ = 3.1–27.5°
b = 12.7961 (14) Å	µ = 0.10 mm−1
c = 7.5828 (11) Å	T = 295 K
β = 106.317 (13)°	Prism, yellow
V = 851.98 (18) Å3	0.35 × 0.15 × 0.05 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	1957 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1149 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.045
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 3.2°
ω scan	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −16→14
Tmin = 0.892, Tmax = 1.000	l = −9→9
7732 measured reflections

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.190	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0742P)2 + 0.0917P] where P = (Fo2 + 2Fc2)/3
1957 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.18 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
F1	0.35050 (15)	0.22275 (14)	0.1895 (2)	0.0959 (6)
N1	1.2165 (3)	0.47627 (19)	0.9490 (4)	0.1097 (9)
N2	1.0706 (2)	0.15887 (19)	0.8205 (3)	0.0900 (8)
C1	0.7452 (2)	0.34429 (17)	0.5304 (3)	0.0566 (6)
C2	0.6299 (3)	0.4089 (2)	0.4263 (3)	0.0704 (7)
H2	0.6434	0.4809	0.4340	0.084*
C3	0.4968 (3)	0.3689 (2)	0.3126 (3)	0.0775 (7)
H3	0.4209	0.4129	0.2442	0.093*
C4	0.4797 (2)	0.2624 (2)	0.3035 (3)	0.0685 (7)
C5	0.5886 (2)	0.1964 (2)	0.4027 (3)	0.0651 (6)
H5	0.5733	0.1245	0.3937	0.078*
C6	0.7208 (2)	0.23631 (18)	0.5158 (3)	0.0606 (6)
H6	0.7952	0.1911	0.5836	0.073*
C7	0.8788 (2)	0.39364 (18)	0.6487 (3)	0.0627 (6)
H7	0.8763	0.4663	0.6451	0.075*
C8	1.0061 (2)	0.35367 (18)	0.7630 (3)	0.0611 (6)
C9	1.1232 (3)	0.4227 (2)	0.8665 (3)	0.0773 (7)
C10	1.0398 (2)	0.2445 (2)	0.7927 (3)	0.0648 (6)

	U11	U22	U33	U12	U13	U23
F1	0.0668 (9)	0.1132 (15)	0.0951 (11)	−0.0038 (8)	0.0019 (8)	−0.0117 (9)
N1	0.1033 (16)	0.0584 (16)	0.131 (2)	−0.0124 (13)	−0.0271 (14)	0.0014 (13)
N2	0.0849 (14)	0.0549 (15)	0.1148 (19)	0.0018 (11)	0.0028 (12)	0.0019 (12)
C1	0.0644 (12)	0.0469 (14)	0.0582 (12)	0.0029 (9)	0.0169 (9)	0.0002 (9)
C2	0.0809 (15)	0.0528 (15)	0.0747 (14)	0.0089 (11)	0.0174 (12)	0.0037 (11)
C3	0.0714 (14)	0.080 (2)	0.0734 (15)	0.0198 (13)	0.0088 (11)	0.0048 (13)
C4	0.0595 (13)	0.080 (2)	0.0642 (14)	−0.0006 (11)	0.0139 (10)	−0.0066 (11)
C5	0.0686 (13)	0.0576 (15)	0.0684 (13)	−0.0032 (11)	0.0179 (11)	−0.0039 (10)
C6	0.0639 (12)	0.0516 (14)	0.0632 (12)	0.0033 (10)	0.0125 (10)	0.0013 (9)
C7	0.0760 (14)	0.0398 (13)	0.0702 (13)	0.0018 (10)	0.0174 (11)	0.0001 (9)
C8	0.0681 (12)	0.0434 (14)	0.0686 (13)	−0.0041 (10)	0.0141 (10)	−0.0015 (9)
C9	0.0803 (15)	0.0485 (16)	0.0899 (17)	−0.0003 (12)	0.0024 (13)	0.0028 (12)
C10	0.0638 (13)	0.0487 (15)	0.0766 (14)	−0.0028 (11)	0.0113 (10)	−0.0037 (11)

F1—C4	1.352 (3)	C3—H3	0.9300
N1—C9	1.135 (3)	C4—C5	1.361 (3)
N2—C10	1.136 (3)	C5—C6	1.370 (3)
C1—C6	1.399 (3)	C5—H5	0.9300
C1—C2	1.396 (3)	C6—H6	0.9300
C1—C7	1.443 (3)	C7—C8	1.342 (3)
C2—C3	1.378 (3)	C7—H7	0.9300
C2—H2	0.9300	C8—C10	1.435 (3)
C3—C4	1.372 (3)	C8—C9	1.440 (3)
C6—C1—C2	117.5 (2)	C4—C5—H5	120.2
C6—C1—C7	124.74 (19)	C6—C5—H5	120.2
C2—C1—C7	117.8 (2)	C5—C6—C1	120.7 (2)
C3—C2—C1	121.9 (3)	C5—C6—H6	119.6
C3—C2—H2	119.0	C1—C6—H6	119.6
C1—C2—H2	119.0	C8—C7—C1	131.6 (2)
C4—C3—C2	118.0 (2)	C8—C7—H7	114.2
C4—C3—H3	121.0	C1—C7—H7	114.2
C2—C3—H3	121.0	C7—C8—C10	125.6 (2)
F1—C4—C5	119.5 (3)	C7—C8—C9	119.7 (2)
F1—C4—C3	118.2 (2)	C10—C8—C9	114.7 (2)
C5—C4—C3	122.3 (2)	N1—C9—C8	179.3 (3)
C4—C5—C6	119.7 (2)	N2—C10—C8	177.8 (2)
C6—C1—C2—C3	−0.2 (3)	C4—C5—C6—C1	0.0 (3)
C7—C1—C2—C3	−178.55 (19)	C2—C1—C6—C5	0.2 (3)
C1—C2—C3—C4	−0.1 (4)	C7—C1—C6—C5	178.50 (19)
C2—C3—C4—F1	−178.78 (19)	C6—C1—C7—C8	1.7 (4)
C2—C3—C4—C5	0.3 (4)	C2—C1—C7—C8	−180.0 (2)
F1—C4—C5—C6	178.84 (19)	C1—C7—C8—C10	0.8 (4)
C3—C4—C5—C6	−0.2 (4)	C1—C7—C8—C9	−179.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N1i	0.93	2.61	3.478 (4)	155
C7—H7···N2ii	0.93	2.51	3.424 (3)	167
C4—F1···Cg1iii	1.35 (1)	3.59 (1)	3.573 (2)	79 (1)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N1i	0.93	2.61	3.478 (4)	155
C7—H7⋯N2ii	0.93	2.51	3.424 (3)	167
C4—F1⋯Cg1iii	1.35 (1)	3.59 (1)	3.573 (2)	79 (1)

Symmetry codes: (i) ; (ii) ; (iii) .