N,N'-Bis(9H-fluoren-9-yl­idene)benzene-1,2-diamine

The title compound, C₃₂H₂₀N₂, was synthesized by the p-toluene­sulfonic acid-assisted Schiff base reaction between 9-fluorenone and o-phenyl­enediamine. The mol­ecule crystallizes in a centrosymmetric space group and is located on a twofold rotation axis. The two fluoren-9-yl­idene moieties adopt a trans configuration as substituents on the linking benzene ring, making the entire mol­ecule chiral.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• R factor = 0.047
• wR factor = 0.117
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and POV-RAY (Persistence of Vision Pty, 2004); software used to prepare material for publication: SHELXL97.

N,N'-Di(9H-fluoren-9-ylidene)benzene-1,2-diamine

Crystal data

C32H20N2	F(000) = 904
Mr = 432.50	Dx = 1.331 Mg m^−3
Monoclinic, C2/c	Melting point: 485 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 14.9807 (6) Å	Cell parameters from 9442 reflections
b = 15.5273 (6) Å	θ = 2.6–32.1°
c = 9.4228 (4) Å	µ = 0.08 mm^−1
β = 99.962 (1)°	T = 100 K
V = 2158.79 (15) Å^3	Irregular, red
Z = 4	0.48 × 0.20 × 0.14 mm

Data collection

Bruker SMART APEX diffractometer	2685 independent reflections
Radiation source: fine-focus sealed tube	2573 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ω scans	θmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −19→19
Tmin = 0.903, Tmax = 0.986	k = −20→20
11410 measured reflections	l = −12→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.117	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0569P)^2 + 2.0007P] where P = (Fo^2 + 2Fc^2)/3
2685 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.40 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.03877 (6)	0.28068 (6)	0.12187 (10)	0.0171 (2)
C1	0.23535 (8)	0.20765 (8)	0.29194 (13)	0.0213 (3)
H1B	0.1910	0.1695	0.3170	0.026*
C2	0.32662 (9)	0.19808 (8)	0.35269 (14)	0.0250 (3)
H2A	0.3444	0.1527	0.4192	0.030*
C3	0.39177 (8)	0.25384 (8)	0.31748 (13)	0.0232 (3)
H3A	0.4536	0.2460	0.3596	0.028*
C4	0.36731 (8)	0.32117 (8)	0.22096 (13)	0.0196 (2)
H4A	0.4119	0.3597	0.1976	0.024*
C5	0.26766 (8)	0.46919 (7)	0.00096 (13)	0.0197 (2)
H5A	0.3307	0.4817	0.0213	0.024*
C6	0.20798 (9)	0.52205 (8)	−0.09030 (13)	0.0226 (3)
H6A	0.2308	0.5710	−0.1328	0.027*
C7	0.11567 (9)	0.50434 (8)	−0.12009 (13)	0.0235 (3)
H7A	0.0765	0.5407	−0.1839	0.028*
C8	0.08001 (8)	0.43373 (8)	−0.05724 (13)	0.0204 (2)
H8A	0.0169	0.4216	−0.0768	0.024*
C9	0.12011 (8)	0.30500 (7)	0.11819 (12)	0.0162 (2)
C10	0.21056 (7)	0.27404 (7)	0.19417 (12)	0.0167 (2)
C11	0.27712 (8)	0.33107 (7)	0.15965 (12)	0.0166 (2)
C12	0.23265 (8)	0.39806 (7)	0.06109 (12)	0.0165 (2)
C13	0.13922 (8)	0.38192 (7)	0.03436 (12)	0.0168 (2)
C14	0.02223 (7)	0.20269 (7)	0.19017 (12)	0.0166 (2)
C15	0.04119 (8)	0.12408 (8)	0.13017 (13)	0.0203 (3)
H15A	0.0690	0.1238	0.0469	0.024*
C16	0.02050 (8)	0.04643 (8)	0.18915 (13)	0.0212 (3)
H16A	0.0342	−0.0064	0.1468	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0177 (5)	0.0154 (4)	0.0187 (5)	−0.0001 (3)	0.0045 (4)	0.0002 (3)
C1	0.0205 (6)	0.0208 (6)	0.0228 (6)	−0.0007 (4)	0.0041 (4)	0.0047 (4)
C2	0.0243 (6)	0.0257 (6)	0.0239 (6)	0.0030 (5)	0.0018 (5)	0.0088 (5)
C3	0.0182 (6)	0.0276 (6)	0.0226 (6)	0.0025 (5)	0.0005 (4)	0.0022 (5)
C4	0.0173 (5)	0.0207 (5)	0.0211 (5)	−0.0012 (4)	0.0040 (4)	−0.0001 (4)
C5	0.0200 (5)	0.0181 (5)	0.0224 (5)	−0.0004 (4)	0.0080 (4)	−0.0005 (4)
C6	0.0293 (6)	0.0167 (5)	0.0236 (6)	0.0002 (4)	0.0098 (5)	0.0039 (4)
C7	0.0271 (6)	0.0203 (6)	0.0227 (6)	0.0034 (5)	0.0032 (5)	0.0051 (4)
C8	0.0201 (5)	0.0197 (5)	0.0210 (5)	0.0011 (4)	0.0024 (4)	0.0011 (4)
C9	0.0189 (5)	0.0147 (5)	0.0149 (5)	0.0012 (4)	0.0031 (4)	−0.0008 (4)
C10	0.0165 (5)	0.0165 (5)	0.0173 (5)	0.0005 (4)	0.0037 (4)	−0.0010 (4)
C11	0.0195 (5)	0.0155 (5)	0.0156 (5)	0.0004 (4)	0.0051 (4)	−0.0010 (4)
C12	0.0189 (5)	0.0159 (5)	0.0153 (5)	0.0018 (4)	0.0046 (4)	−0.0015 (4)
C13	0.0193 (5)	0.0148 (5)	0.0167 (5)	0.0000 (4)	0.0046 (4)	−0.0009 (4)
C14	0.0136 (5)	0.0171 (5)	0.0187 (5)	0.0004 (4)	0.0016 (4)	0.0012 (4)
C15	0.0203 (6)	0.0204 (6)	0.0216 (5)	0.0010 (4)	0.0072 (4)	−0.0009 (4)
C16	0.0228 (6)	0.0164 (5)	0.0245 (6)	0.0014 (4)	0.0046 (5)	−0.0026 (4)

Geometric parameters (Å, º)

N1—C9	1.2818 (15)	C7—C8	1.3956 (17)
N1—C14	1.4133 (14)	C7—H7A	0.9500
C1—C10	1.3897 (16)	C8—C13	1.3835 (16)
C1—C2	1.3957 (17)	C8—H8A	0.9500
C1—H1B	0.9500	C9—C13	1.4868 (15)
C2—C3	1.3873 (18)	C9—C10	1.4980 (15)
C2—H2A	0.9500	C10—C11	1.4129 (15)
C3—C4	1.3925 (17)	C11—C12	1.4745 (15)
C3—H3A	0.9500	C12—C13	1.4011 (16)
C4—C11	1.3830 (16)	C14—C15	1.3949 (16)
C4—H4A	0.9500	C14—C14^i	1.405 (2)
C5—C12	1.3852 (16)	C15—C16	1.3851 (16)
C5—C6	1.3951 (17)	C15—H15A	0.9500
C5—H5A	0.9500	C16—C16^i	1.391 (2)
C6—C7	1.3901 (18)	C16—H16A	0.9500
C6—H6A	0.9500
C9—N1—C14	120.48 (10)	N1—C9—C13	121.49 (10)
C10—C1—C2	118.77 (11)	N1—C9—C10	132.69 (10)
C10—C1—H1B	120.6	C13—C9—C10	105.68 (9)
C2—C1—H1B	120.6	C1—C10—C11	119.95 (11)
C3—C2—C1	121.02 (11)	C1—C10—C9	132.13 (11)
C3—C2—H2A	119.5	C11—C10—C9	107.75 (10)
C1—C2—H2A	119.5	C4—C11—C10	120.76 (10)
C2—C3—C4	120.54 (11)	C4—C11—C12	130.08 (10)
C2—C3—H3A	119.7	C10—C11—C12	109.10 (10)
C4—C3—H3A	119.7	C5—C12—C13	120.41 (10)
C11—C4—C3	118.95 (11)	C5—C12—C11	131.17 (11)
C11—C4—H4A	120.5	C13—C12—C11	108.39 (10)
C3—C4—H4A	120.5	C8—C13—C12	121.39 (10)
C12—C5—C6	118.27 (11)	C8—C13—C9	129.56 (11)
C12—C5—H5A	120.9	C12—C13—C9	109.05 (10)
C6—C5—H5A	120.9	C15—C14—C14^i	118.90 (7)
C7—C6—C5	121.14 (11)	C15—C14—N1	120.08 (10)
C7—C6—H6A	119.4	C14^i—C14—N1	120.67 (6)
C5—C6—H6A	119.4	C16—C15—C14	121.58 (11)
C6—C7—C8	120.68 (11)	C16—C15—H15A	119.2
C6—C7—H7A	119.7	C14—C15—H15A	119.2
C8—C7—H7A	119.7	C15—C16—C16^i	119.47 (7)
C13—C8—C7	118.06 (11)	C15—C16—H16A	120.3
C13—C8—H8A	121.0	C16^i—C16—H16A	120.3
C7—C8—H8A	121.0
C10—C1—C2—C3	0.41 (19)	C6—C5—C12—C11	179.94 (11)
C1—C2—C3—C4	0.4 (2)	C4—C11—C12—C5	0.6 (2)
C2—C3—C4—C11	−0.63 (18)	C10—C11—C12—C5	177.62 (11)
C12—C5—C6—C7	0.26 (18)	C4—C11—C12—C13	−177.41 (11)
C5—C6—C7—C8	1.09 (19)	C10—C11—C12—C13	−0.40 (12)
C6—C7—C8—C13	−0.42 (18)	C7—C8—C13—C12	−1.59 (17)
C14—N1—C9—C13	173.64 (10)	C7—C8—C13—C9	178.15 (11)
C14—N1—C9—C10	−11.38 (19)	C5—C12—C13—C8	2.97 (17)
C2—C1—C10—C11	−0.94 (18)	C11—C12—C13—C8	−178.75 (10)
C2—C1—C10—C9	−175.58 (12)	C5—C12—C13—C9	−176.81 (10)
N1—C9—C10—C1	1.2 (2)	C11—C12—C13—C9	1.46 (12)
C13—C9—C10—C1	176.77 (12)	N1—C9—C13—C8	−5.51 (18)
N1—C9—C10—C11	−173.92 (12)	C10—C9—C13—C8	178.32 (11)
C13—C9—C10—C11	1.64 (12)	N1—C9—C13—C12	174.26 (10)
C3—C4—C11—C10	0.09 (17)	C10—C9—C13—C12	−1.91 (12)
C3—C4—C11—C12	176.80 (11)	C9—N1—C14—C15	−68.89 (15)
C1—C10—C11—C4	0.70 (17)	C9—N1—C14—C14^i	117.97 (15)
C9—C10—C11—C4	176.53 (10)	C14^i—C14—C15—C16	−2.6 (2)
C1—C10—C11—C12	−176.64 (10)	N1—C14—C15—C16	−175.85 (11)
C9—C10—C11—C12	−0.81 (12)	C14—C15—C16—C16^i	0.2 (2)
C6—C5—C12—C13	−2.24 (17)

Symmetry code: (i) −x, y, −z+1/2.