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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.
Supporting information
CCDC reference: 271810
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
No syntax errors found
No errors found in this datablock
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(9
H-fluoren-9-ylidene)benzene-1,2-diamine
top
Crystal data top
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) Å3 | Irregular, red |
Z = 4 | 0.48 × 0.20 × 0.14 mm |
Data collection top
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 top
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0569P)2 + 2.0007P] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—C14i | 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—C16i | 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—C14i | 118.90 (7) |
C7—C6—C5 | 121.14 (11) | C15—C14—N1 | 120.08 (10) |
C7—C6—H6A | 119.4 | C14i—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—C16i | 119.47 (7) |
C13—C8—C7 | 118.06 (11) | C15—C16—H16A | 120.3 |
C13—C8—H8A | 121.0 | C16i—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—C14i | 117.97 (15) |
C9—C10—C11—C4 | 176.53 (10) | C14i—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—C16i | 0.2 (2) |
C6—C5—C12—C13 | −2.24 (17) | | |
Symmetry code: (i) −x, y, −z+1/2. |
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