N-(9H-Fluoren-9-yl-idene)-4-methyl-aniline.

In the title compound, C(20)H(15)N, the fluorene unit is essentially planar [r.m.s. deviation 0.0334 Å] and the benzene ring bound to the imine N atom bears a methyl group which is nearly coplanar [dihedral angle 0.5 (1)°]. The dihedral angle between the substituent benzene ring and the 9H-fluoren-9-imine unit is 71.1 (3)°. Inter-molecular π-π inter-actions between the benzene rings of adjacent fluorene units [centroid-centroid distance 3.8081 (13) Å] are present in the crystal structure, resulting in a one-dimensional supra-molecular architecture.

Related literature

For the properties of Schiff bases, see: Xu et al. (2007 ▶); Tanaka et al. (2006 ▶). For the properties of fluorene derivatives, see: Saragi et al. (2004 ▶). For related structures, see: Glagovich et al. (2004 ▶); Peters et al. (1998 ▶); Pierre et al. (1997 ▶).

Experimental

Crystal data

C20H15N

M = 269.33

Monoclinic,

a = 5.6423 (10) Å

b = 12.187 (2) Å

c = 21.310 (4) Å

β = 94.441 (2)°

V = 1460.9 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 294 K

0.35 × 0.17 × 0.09 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.976, T max = 0.994

10793 measured reflections

2711 independent reflections

1779 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.115

S = 1.01

2711 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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/S1600536809020765/si2179sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020765/si2179Isup2.hkl

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

C20H15N	F(000) = 568
Mr = 269.33	Dx = 1.225 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 5.6423 (10) Å	Cell parameters from 1911 reflections
b = 12.187 (2) Å	θ = 2.5–22.3°
c = 21.310 (4) Å	µ = 0.07 mm−1
β = 94.441 (2)°	T = 294 K
V = 1460.9 (5) Å3	Block, yellow
Z = 4	0.35 × 0.17 × 0.09 mm

Bruker SMART APEX CCD area-detector diffractometer	2711 independent reflections
Radiation source: fine-focus sealed tube	1779 reflections with I > 2σ(I)
graphite	Rint = 0.042
phi and ω scans	θmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.976, Tmax = 0.994	k = −14→14
10793 measured reflections	l = −25→25

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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.052P)2 + 0.1725P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2711 reflections	Δρmax = 0.13 e Å−3
192 parameters	Δρmin = −0.14 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0105 (19)

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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
C1	0.0001 (3)	0.30235 (15)	0.13059 (9)	0.0507 (5)
H1	−0.0938	0.3086	0.0929	0.061*
C2	−0.0545 (4)	0.36053 (16)	0.18339 (10)	0.0582 (5)
H2	−0.1869	0.4062	0.1810	0.070*
C3	0.0836 (4)	0.35188 (16)	0.23918 (10)	0.0604 (5)
H3	0.0452	0.3931	0.2737	0.072*
C4	0.2787 (3)	0.28289 (15)	0.24478 (9)	0.0544 (5)
H4	0.3701	0.2762	0.2828	0.065*
C5	0.3348 (3)	0.22414 (13)	0.19248 (8)	0.0435 (4)
C6	0.5230 (3)	0.14217 (13)	0.18583 (8)	0.0433 (4)
C7	0.7076 (3)	0.10822 (14)	0.22712 (9)	0.0508 (5)
H7	0.7270	0.1372	0.2676	0.061*
C8	0.8643 (3)	0.03010 (15)	0.20743 (9)	0.0549 (5)
H8	0.9901	0.0065	0.2349	0.066*
C9	0.8350 (3)	−0.01288 (16)	0.14735 (9)	0.0557 (5)
H9	0.9409	−0.0657	0.1350	0.067*
C10	0.6513 (3)	0.02124 (14)	0.10530 (9)	0.0506 (5)
H10	0.6328	−0.0077	0.0648	0.061*
C11	0.4954 (3)	0.09953 (13)	0.12487 (8)	0.0432 (4)
C12	0.2980 (3)	0.15766 (13)	0.08907 (8)	0.0440 (4)
C13	0.1986 (3)	0.23442 (13)	0.13519 (8)	0.0428 (4)
C14	0.0834 (3)	0.21043 (15)	−0.00479 (8)	0.0481 (5)
C15	−0.1301 (3)	0.17101 (16)	−0.03143 (9)	0.0544 (5)
H15	−0.1735	0.0986	−0.0246	0.065*
C16	−0.2793 (4)	0.23849 (16)	−0.06821 (9)	0.0598 (5)
H16	−0.4241	0.2110	−0.0852	0.072*
C17	−0.2197 (4)	0.34635 (17)	−0.08065 (9)	0.0579 (5)
C18	−0.0037 (4)	0.38372 (16)	−0.05457 (9)	0.0612 (5)
H18	0.0417	0.4554	−0.0625	0.073*
C19	0.1475 (4)	0.31784 (16)	−0.01699 (9)	0.0592 (5)
H19	0.2921	0.3454	0.0001	0.071*
C20	−0.3829 (4)	0.4195 (2)	−0.12150 (12)	0.0880 (8)
H20A	−0.3234	0.4263	−0.1623	0.132*
H20B	−0.3899	0.4907	−0.1024	0.132*
H20C	−0.5393	0.3880	−0.1257	0.132*
N1	0.2459 (3)	0.14086 (12)	0.03045 (7)	0.0521 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0542 (11)	0.0462 (10)	0.0518 (11)	0.0015 (9)	0.0048 (9)	0.0011 (9)
C2	0.0594 (12)	0.0508 (11)	0.0659 (14)	0.0066 (9)	0.0144 (11)	−0.0045 (10)
C3	0.0717 (14)	0.0513 (12)	0.0600 (13)	0.0007 (10)	0.0164 (11)	−0.0119 (10)
C4	0.0629 (12)	0.0494 (11)	0.0507 (11)	−0.0054 (9)	0.0037 (9)	−0.0071 (9)
C5	0.0486 (10)	0.0379 (9)	0.0443 (10)	−0.0061 (8)	0.0062 (8)	−0.0038 (8)
C6	0.0477 (10)	0.0395 (9)	0.0429 (10)	−0.0065 (8)	0.0040 (8)	0.0014 (8)
C7	0.0565 (11)	0.0494 (11)	0.0457 (11)	−0.0039 (9)	−0.0005 (9)	0.0003 (9)
C8	0.0497 (11)	0.0555 (12)	0.0587 (13)	0.0015 (9)	−0.0008 (10)	0.0083 (10)
C9	0.0585 (12)	0.0521 (11)	0.0578 (13)	0.0085 (9)	0.0123 (10)	0.0071 (10)
C10	0.0630 (12)	0.0441 (10)	0.0455 (11)	0.0034 (9)	0.0102 (9)	0.0023 (8)
C11	0.0497 (10)	0.0365 (9)	0.0438 (10)	−0.0017 (8)	0.0053 (8)	0.0022 (8)
C12	0.0509 (11)	0.0381 (9)	0.0434 (11)	−0.0027 (8)	0.0064 (8)	0.0007 (8)
C13	0.0494 (10)	0.0350 (9)	0.0446 (10)	−0.0043 (8)	0.0075 (8)	−0.0004 (8)
C14	0.0591 (12)	0.0486 (10)	0.0366 (10)	0.0046 (9)	0.0029 (9)	−0.0027 (8)
C15	0.0632 (12)	0.0498 (11)	0.0502 (11)	−0.0031 (10)	0.0038 (10)	0.0021 (9)
C16	0.0562 (12)	0.0647 (13)	0.0572 (12)	−0.0059 (10)	−0.0030 (10)	0.0009 (10)
C17	0.0627 (13)	0.0626 (13)	0.0478 (11)	0.0034 (10)	0.0006 (10)	0.0082 (10)
C18	0.0700 (14)	0.0521 (12)	0.0610 (13)	−0.0019 (10)	0.0020 (11)	0.0089 (10)
C19	0.0609 (12)	0.0554 (12)	0.0597 (13)	−0.0027 (10)	−0.0046 (10)	0.0022 (10)
C20	0.0844 (17)	0.0904 (18)	0.0862 (18)	0.0081 (14)	−0.0126 (14)	0.0261 (14)
N1	0.0638 (10)	0.0489 (9)	0.0431 (9)	0.0066 (8)	0.0002 (8)	−0.0012 (7)

C1—C2	1.385 (3)	C10—H10	0.9300
C1—C13	1.390 (2)	C11—C12	1.481 (2)
C1—H1	0.9300	C12—N1	1.278 (2)
C2—C3	1.374 (3)	C12—C13	1.497 (2)
C2—H2	0.9300	C14—C15	1.378 (2)
C3—C4	1.383 (3)	C14—C19	1.388 (3)
C3—H3	0.9300	C14—N1	1.420 (2)
C4—C5	1.382 (2)	C15—C16	1.378 (3)
C4—H4	0.9300	C15—H15	0.9300
C5—C13	1.397 (2)	C16—C17	1.387 (3)
C5—C6	1.473 (2)	C16—H16	0.9300
C6—C7	1.374 (2)	C17—C18	1.377 (3)
C6—C11	1.397 (2)	C17—C20	1.509 (3)
C7—C8	1.386 (3)	C18—C19	1.381 (3)
C7—H7	0.9300	C18—H18	0.9300
C8—C9	1.381 (3)	C19—H19	0.9300
C8—H8	0.9300	C20—H20A	0.9600
C9—C10	1.381 (2)	C20—H20B	0.9600
C9—H9	0.9300	C20—H20C	0.9600
C10—C11	1.384 (2)
C2—C1—C13	118.45 (18)	C6—C11—C12	109.05 (15)
C2—C1—H1	120.8	N1—C12—C11	122.27 (16)
C13—C1—H1	120.8	N1—C12—C13	132.28 (16)
C3—C2—C1	121.13 (18)	C11—C12—C13	105.42 (14)
C3—C2—H2	119.4	C1—C13—C5	120.05 (16)
C1—C2—H2	119.4	C1—C13—C12	131.81 (16)
C2—C3—C4	121.03 (18)	C5—C13—C12	108.00 (15)
C2—C3—H3	119.5	C15—C14—C19	118.94 (17)
C4—C3—H3	119.5	C15—C14—N1	121.18 (17)
C5—C4—C3	118.41 (18)	C19—C14—N1	119.68 (17)
C5—C4—H4	120.8	C16—C15—C14	120.18 (18)
C3—C4—H4	120.8	C16—C15—H15	119.9
C4—C5—C13	120.91 (17)	C14—C15—H15	119.9
C4—C5—C6	129.85 (17)	C15—C16—C17	121.85 (19)
C13—C5—C6	109.18 (15)	C15—C16—H16	119.1
C7—C6—C11	120.53 (16)	C17—C16—H16	119.1
C7—C6—C5	131.23 (16)	C18—C17—C16	117.14 (18)
C11—C6—C5	108.22 (15)	C18—C17—C20	121.3 (2)
C6—C7—C8	118.85 (18)	C16—C17—C20	121.6 (2)
C6—C7—H7	120.6	C17—C18—C19	121.97 (19)
C8—C7—H7	120.6	C17—C18—H18	119.0
C9—C8—C7	120.51 (18)	C19—C18—H18	119.0
C9—C8—H8	119.7	C18—C19—C14	119.90 (18)
C7—C8—H8	119.7	C18—C19—H19	120.1
C10—C9—C8	121.14 (18)	C14—C19—H19	120.1
C10—C9—H9	119.4	C17—C20—H20A	109.5
C8—C9—H9	119.4	C17—C20—H20B	109.5
C9—C10—C11	118.36 (17)	H20A—C20—H20B	109.5
C9—C10—H10	120.8	C17—C20—H20C	109.5
C11—C10—H10	120.8	H20A—C20—H20C	109.5
C10—C11—C6	120.60 (17)	H20B—C20—H20C	109.5
C10—C11—C12	130.17 (16)	C12—N1—C14	120.76 (15)
C13—C1—C2—C3	0.1 (3)	C2—C1—C13—C5	1.4 (3)
C1—C2—C3—C4	−1.4 (3)	C2—C1—C13—C12	176.50 (17)
C2—C3—C4—C5	1.2 (3)	C4—C5—C13—C1	−1.6 (3)
C3—C4—C5—C13	0.3 (3)	C6—C5—C13—C1	176.08 (15)
C3—C4—C5—C6	−176.88 (17)	C4—C5—C13—C12	−177.78 (15)
C4—C5—C6—C7	−6.8 (3)	C6—C5—C13—C12	−0.07 (18)
C13—C5—C6—C7	175.76 (17)	N1—C12—C13—C1	8.8 (3)
C4—C5—C6—C11	175.26 (18)	C11—C12—C13—C1	−173.40 (17)
C13—C5—C6—C11	−2.18 (18)	N1—C12—C13—C5	−175.62 (18)
C11—C6—C7—C8	−0.7 (3)	C11—C12—C13—C5	2.14 (17)
C5—C6—C7—C8	−178.41 (17)	C19—C14—C15—C16	−1.7 (3)
C6—C7—C8—C9	−0.1 (3)	N1—C14—C15—C16	−176.54 (17)
C7—C8—C9—C10	0.6 (3)	C14—C15—C16—C17	1.2 (3)
C8—C9—C10—C11	−0.3 (3)	C15—C16—C17—C18	0.0 (3)
C9—C10—C11—C6	−0.4 (3)	C15—C16—C17—C20	179.4 (2)
C9—C10—C11—C12	174.14 (17)	C16—C17—C18—C19	−0.7 (3)
C7—C6—C11—C10	1.0 (3)	C20—C17—C18—C19	179.9 (2)
C5—C6—C11—C10	179.15 (15)	C17—C18—C19—C14	0.2 (3)
C7—C6—C11—C12	−174.66 (15)	C15—C14—C19—C18	1.0 (3)
C5—C6—C11—C12	3.53 (18)	N1—C14—C19—C18	175.92 (17)
C10—C11—C12—N1	−0.5 (3)	C11—C12—N1—C14	−169.33 (16)
C6—C11—C12—N1	174.52 (16)	C13—C12—N1—C14	8.1 (3)
C10—C11—C12—C13	−178.57 (17)	C15—C14—N1—C12	−115.92 (19)
C6—C11—C12—C13	−3.52 (18)	C19—C14—N1—C12	69.2 (2)