N,N'-[(2E,3E)-Butane-2,3-diylidene]bis[4-fluoro-2-(1-phenyl-eth-yl)aniline].

The title mol-ecule, C32H30F2N2, a product of the condensation reaction of butane-2,3-dione and 4-fluoro-2-(1-phenyl-eth-yl)aniline, is located about an inversion centre. In the asymmetric unit, the dihedral angle between the planes of the benzene and phenyl rings is 84.27 (5)°. Neither hydrogen bonding nor aromatic stacking is observed in the crystal structure.

Related literature

For the synthesis of α-di­imine ligands, see: Grasa et al. (2001 ▶); Williams et al. (2008 ▶); Hanhan et al. (2012 ▶); Partyka (2011 ▶); Yuan et al. (2012 ▶). For related structures, see: Zou et al. (2008 ▶); Lohr et al. (2011 ▶).

Experimental

Crystal data

C32H30F2N2

M = 480.58

Monoclinic,

a = 11.5335 (11) Å

b = 9.5024 (12) Å

c = 12.1318 (14) Å

β = 91.660 (11)°

V = 1329.0 (3) Å3

Z = 2

Cu Kα radiation

μ = 0.64 mm−1

T = 295 K

0.35 × 0.28 × 0.26 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.808, T max = 0.852

5982 measured reflections

2507 independent reflections

2132 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.118

S = 1.07

2507 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814002657/rk2419sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002657/rk2419Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814002657/rk2419Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C32H30F2N2	F(000) = 508
Mr = 480.58	Dx = 1.201 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 11.5335 (11) Å	Cell parameters from 2620 reflections
b = 9.5024 (12) Å	θ = 5.2–70.8°
c = 12.1318 (14) Å	µ = 0.64 mm−1
β = 91.660 (11)°	T = 295 K
V = 1329.0 (3) Å3	Block, clear light yellow
Z = 2	0.35 × 0.28 × 0.26 mm

Bruker APEXII CCD diffractometer	2507 independent reflections
Radiation source: fine-focus sealed tube	2132 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 70.5°, θmin = 5.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→12
Tmin = 0.808, Tmax = 0.852	k = −11→10
5982 measured reflections	l = −14→14

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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.056P)2 + 0.1881P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2507 reflections	Δρmax = 0.18 e Å−3
166 parameters	Δρmin = −0.15 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: 0.0100 (10)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
N1	0.37261 (9)	0.49441 (12)	0.57384 (9)	0.0406 (3)
F1	−0.02542 (7)	0.78857 (12)	0.66670 (9)	0.0687 (3)
C1	0.57482 (13)	0.64883 (19)	0.75155 (16)	0.0602 (4)
H1	0.5841	0.5539	0.7683	0.072*
C2	0.67019 (14)	0.7270 (2)	0.72255 (19)	0.0747 (6)
H2	0.7426	0.6844	0.7197	0.090*
C3	0.65862 (15)	0.8671 (2)	0.69791 (18)	0.0743 (6)
H3	0.7224	0.9194	0.6769	0.089*
C4	0.55119 (15)	0.9295 (2)	0.70466 (16)	0.0687 (5)
H4	0.5430	1.0251	0.6899	0.082*
C5	0.45519 (13)	0.85116 (16)	0.73331 (14)	0.0543 (4)
H5	0.3832	0.8946	0.7371	0.065*
C6	0.46540 (11)	0.70923 (15)	0.75624 (11)	0.0420 (3)
C7	0.36098 (11)	0.61988 (15)	0.78526 (11)	0.0419 (3)
H7	0.3860	0.5215	0.7814	0.050*
C8	0.26187 (10)	0.63660 (13)	0.70095 (10)	0.0361 (3)
C9	0.16094 (11)	0.71082 (15)	0.72229 (11)	0.0422 (3)
H9	0.1525	0.7555	0.7898	0.051*
C10	0.07376 (11)	0.71744 (15)	0.64271 (13)	0.0468 (3)
C11	0.08083 (12)	0.65451 (17)	0.54169 (13)	0.0518 (4)
H11	0.0199	0.6601	0.4899	0.062*
C12	0.18142 (12)	0.58231 (17)	0.51907 (11)	0.0488 (4)
H12	0.1885	0.5385	0.4510	0.059*
C13	0.27209 (11)	0.57440 (14)	0.59672 (10)	0.0379 (3)
C14	0.32418 (14)	0.6453 (2)	0.90437 (13)	0.0628 (5)
H14A	0.3068	0.7433	0.9142	0.094*
H14B	0.3862	0.6185	0.9545	0.094*
H14C	0.2566	0.5902	0.9188	0.094*
C15	0.44839 (10)	0.54573 (14)	0.51063 (10)	0.0399 (3)
C16	0.44521 (14)	0.68862 (16)	0.45826 (14)	0.0558 (4)
H16A	0.3815	0.7414	0.4862	0.084*
H16B	0.4356	0.6788	0.3798	0.084*
H16C	0.5165	0.7371	0.4753	0.084*

	U11	U22	U33	U12	U13	U23
N1	0.0385 (6)	0.0450 (6)	0.0388 (6)	0.0027 (5)	0.0096 (4)	−0.0018 (5)
F1	0.0418 (5)	0.0843 (7)	0.0801 (7)	0.0223 (4)	0.0027 (4)	−0.0130 (5)
C1	0.0394 (7)	0.0582 (10)	0.0828 (11)	0.0038 (7)	−0.0031 (7)	−0.0062 (8)
C2	0.0369 (8)	0.0801 (13)	0.1072 (16)	−0.0020 (8)	0.0043 (9)	−0.0174 (11)
C3	0.0512 (9)	0.0828 (13)	0.0896 (13)	−0.0260 (9)	0.0173 (9)	−0.0201 (11)
C4	0.0681 (11)	0.0520 (10)	0.0868 (13)	−0.0131 (8)	0.0148 (10)	−0.0048 (8)
C5	0.0465 (8)	0.0472 (8)	0.0698 (10)	0.0001 (6)	0.0093 (7)	−0.0048 (7)
C6	0.0372 (6)	0.0461 (8)	0.0427 (7)	−0.0009 (5)	−0.0001 (5)	−0.0071 (6)
C7	0.0396 (7)	0.0438 (7)	0.0423 (7)	−0.0011 (5)	0.0004 (5)	0.0002 (6)
C8	0.0328 (6)	0.0381 (7)	0.0377 (6)	−0.0033 (5)	0.0066 (5)	−0.0001 (5)
C9	0.0387 (6)	0.0454 (7)	0.0431 (7)	0.0000 (5)	0.0085 (5)	−0.0065 (5)
C10	0.0341 (6)	0.0484 (8)	0.0583 (8)	0.0063 (5)	0.0066 (6)	−0.0022 (6)
C11	0.0407 (7)	0.0626 (9)	0.0515 (8)	0.0045 (6)	−0.0070 (6)	−0.0020 (7)
C12	0.0481 (8)	0.0597 (9)	0.0386 (7)	0.0038 (6)	0.0011 (6)	−0.0071 (6)
C13	0.0353 (6)	0.0406 (7)	0.0383 (6)	0.0003 (5)	0.0087 (5)	0.0010 (5)
C14	0.0585 (9)	0.0879 (13)	0.0420 (8)	−0.0129 (9)	0.0003 (7)	0.0006 (8)
C15	0.0411 (7)	0.0427 (7)	0.0363 (6)	0.0042 (6)	0.0088 (5)	−0.0019 (5)
C16	0.0559 (8)	0.0505 (9)	0.0623 (9)	0.0119 (7)	0.0237 (7)	0.0108 (7)

N1—C15	1.2761 (16)	C8—C9	1.3917 (17)
N1—C13	1.4204 (15)	C8—C13	1.4039 (17)
F1—C10	1.3673 (15)	C9—C10	1.375 (2)
C1—C2	1.382 (2)	C9—H9	0.9300
C1—C6	1.3890 (19)	C10—C11	1.368 (2)
C1—H1	0.9300	C11—C12	1.382 (2)
C2—C3	1.370 (3)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.3892 (19)
C3—C4	1.378 (3)	C12—H12	0.9300
C3—H3	0.9300	C14—H14A	0.9600
C4—C5	1.387 (2)	C14—H14B	0.9600
C4—H4	0.9300	C14—H14C	0.9600
C5—C6	1.381 (2)	C15—C16	1.4992 (19)
C5—H5	0.9300	C15—C15i	1.502 (2)
C6—C7	1.5231 (18)	C16—H16A	0.9600
C7—C8	1.5200 (18)	C16—H16B	0.9600
C7—C14	1.537 (2)	C16—H16C	0.9600
C7—H7	0.9800
C15—N1—C13	119.34 (11)	C10—C9—H9	120.3
C2—C1—C6	121.28 (17)	C8—C9—H9	120.3
C2—C1—H1	119.4	F1—C10—C11	118.60 (13)
C6—C1—H1	119.4	F1—C10—C9	118.19 (13)
C3—C2—C1	120.33 (16)	C11—C10—C9	123.20 (12)
C3—C2—H2	119.8	C10—C11—C12	117.84 (13)
C1—C2—H2	119.8	C10—C11—H11	121.1
C2—C3—C4	119.17 (16)	C12—C11—H11	121.1
C2—C3—H3	120.4	C11—C12—C13	120.79 (13)
C4—C3—H3	120.4	C11—C12—H12	119.6
C3—C4—C5	120.61 (17)	C13—C12—H12	119.6
C3—C4—H4	119.7	C12—C13—C8	120.45 (12)
C5—C4—H4	119.7	C12—C13—N1	119.94 (12)
C6—C5—C4	120.71 (15)	C8—C13—N1	119.45 (11)
C6—C5—H5	119.6	C7—C14—H14A	109.5
C4—C5—H5	119.6	C7—C14—H14B	109.5
C5—C6—C1	117.87 (14)	H14A—C14—H14B	109.5
C5—C6—C7	121.83 (12)	C7—C14—H14C	109.5
C1—C6—C7	120.30 (13)	H14A—C14—H14C	109.5
C8—C7—C6	111.74 (11)	H14B—C14—H14C	109.5
C8—C7—C14	113.17 (12)	N1—C15—C16	126.30 (12)
C6—C7—C14	111.80 (12)	N1—C15—C15i	116.24 (15)
C8—C7—H7	106.5	C16—C15—C15i	117.44 (14)
C6—C7—H7	106.5	C15—C16—H16A	109.5
C14—C7—H7	106.5	C15—C16—H16B	109.5
C9—C8—C13	118.26 (12)	H16A—C16—H16B	109.5
C9—C8—C7	122.99 (12)	C15—C16—H16C	109.5
C13—C8—C7	118.74 (11)	H16A—C16—H16C	109.5
C10—C9—C8	119.41 (12)	H16B—C16—H16C	109.5
C6—C1—C2—C3	0.2 (3)	C7—C8—C9—C10	−178.02 (13)
C1—C2—C3—C4	1.3 (3)	C8—C9—C10—F1	178.66 (12)
C2—C3—C4—C5	−1.6 (3)	C8—C9—C10—C11	−0.3 (2)
C3—C4—C5—C6	0.4 (3)	F1—C10—C11—C12	−179.60 (13)
C4—C5—C6—C1	1.1 (2)	C9—C10—C11—C12	−0.7 (2)
C4—C5—C6—C7	−178.53 (14)	C10—C11—C12—C13	0.0 (2)
C2—C1—C6—C5	−1.4 (2)	C11—C12—C13—C8	1.7 (2)
C2—C1—C6—C7	178.26 (16)	C11—C12—C13—N1	177.16 (13)
C5—C6—C7—C8	51.52 (17)	C9—C8—C13—C12	−2.62 (19)
C1—C6—C7—C8	−128.13 (14)	C7—C8—C13—C12	177.29 (12)
C5—C6—C7—C14	−76.48 (18)	C9—C8—C13—N1	−178.09 (11)
C1—C6—C7—C14	103.86 (17)	C7—C8—C13—N1	1.83 (18)
C6—C7—C8—C9	−107.17 (14)	C15—N1—C13—C12	77.96 (17)
C14—C7—C8—C9	20.09 (19)	C15—N1—C13—C8	−106.56 (14)
C6—C7—C8—C13	72.91 (15)	C13—N1—C15—C16	2.1 (2)
C14—C7—C8—C13	−159.82 (13)	C13—N1—C15—C15i	−179.36 (13)
C13—C8—C9—C10	1.89 (19)