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The molecule of 1,4-bis(benzylamino)benzene, C20H20N2, lies on a center of inversion in its crystal structure; adjacent pyramidal amino groups are linked by hydrogen bonds into a layer motif.
Supporting information
CCDC reference: 621347
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.002 Å
- R factor = 0.039
- wR factor = 0.105
- Data-to-parameter ratio = 12.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
1,4-bis(benzylamino)benzene
top
Crystal data top
C20H20N2 | F(000) = 308 |
Mr = 288.38 | Dx = 1.222 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1867 reflections |
a = 11.912 (1) Å | θ = 3.4–26.3° |
b = 5.5402 (8) Å | µ = 0.07 mm−1 |
c = 11.895 (1) Å | T = 295 K |
β = 93.47 (1)° | Plate, colorless |
V = 783.5 (2) Å3 | 0.44 × 0.34 × 0.14 mm |
Z = 2 | |
Data collection top
Bruker APEX-II area-detector diffractometer | 1420 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.020 |
Graphite monochromator | θmax = 27.5°, θmin = 3.4° |
φ and ω scans | h = −15→15 |
6428 measured reflections | k = −7→7 |
1800 independent reflections | l = −15→15 |
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)] = 0.039 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.105 | All H-atom parameters refined |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0508P)2 + 0.0816P] where P = (Fo2 + 2Fc2)/3 |
1800 reflections | (Δ/σ)max = 0.001 |
140 parameters | Δρmax = 0.12 e Å−3 |
10 restraints | Δρmin = −0.15 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.5592 (1) | 0.7203 (2) | 0.7094 (1) | 0.0474 (3) | |
C1 | 0.4150 (1) | 0.5994 (2) | 0.4306 (1) | 0.0430 (3) | |
C2 | 0.4490 (1) | 0.7087 (2) | 0.5316 (1) | 0.0423 (3) | |
C3 | 0.5340 (1) | 0.6133 (2) | 0.6031 (1) | 0.0386 (3) | |
C4 | 0.6716 (1) | 0.7110 (2) | 0.7644 (1) | 0.0486 (3) | |
C5 | 0.7573 (1) | 0.8780 (2) | 0.7172 (1) | 0.0451 (3) | |
C6 | 0.8099 (1) | 1.0548 (3) | 0.7838 (1) | 0.0595 (4) | |
C7 | 0.8860 (1) | 1.2128 (3) | 0.7406 (2) | 0.0747 (5) | |
C8 | 0.9102 (1) | 1.1992 (3) | 0.6296 (2) | 0.0740 (5) | |
C9 | 0.8596 (1) | 1.0248 (3) | 0.5619 (1) | 0.0678 (4) | |
C10 | 0.7847 (1) | 0.8640 (3) | 0.6052 (1) | 0.0567 (3) | |
H1n | 0.530 (1) | 0.864 (2) | 0.715 (1) | 0.057 (4)* | |
H1 | 0.355 (1) | 0.672 (2) | 0.384 (1) | 0.054 (3)* | |
H2 | 0.413 (1) | 0.852 (2) | 0.553 (1) | 0.052 (3)* | |
H4a | 0.662 (1) | 0.754 (2) | 0.842 (1) | 0.061 (4)* | |
H4b | 0.697 (1) | 0.546 (2) | 0.761 (1) | 0.059 (4)* | |
H6 | 0.792 (1) | 1.066 (3) | 0.862 (1) | 0.075 (5)* | |
H7 | 0.922 (2) | 1.332 (3) | 0.788 (1) | 0.099 (6)* | |
H8 | 0.962 (1) | 1.310 (3) | 0.599 (1) | 0.089 (5)* | |
H9 | 0.875 (1) | 1.012 (3) | 0.485 (1) | 0.088 (5)* | |
H10 | 0.750 (1) | 0.739 (2) | 0.559 (1) | 0.067 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.051 (1) | 0.049 (1) | 0.043 (1) | 0.001 (1) | 0.006 (1) | −0.011 (1) |
C1 | 0.046 (1) | 0.040 (1) | 0.043 (1) | 0.005 (1) | 0.003 (1) | 0.001 (1) |
C2 | 0.049 (1) | 0.033 (1) | 0.046 (1) | 0.004 (1) | 0.011 (1) | −0.003 (1) |
C3 | 0.043 (1) | 0.037 (1) | 0.037 (1) | −0.005 (1) | 0.010 (1) | −0.002 (1) |
C4 | 0.060 (1) | 0.049 (1) | 0.036 (1) | −0.001 (1) | 0.000 (1) | −0.001 (1) |
C5 | 0.043 (1) | 0.045 (1) | 0.047 (1) | 0.006 (1) | −0.002 (1) | −0.001 (1) |
C6 | 0.057 (1) | 0.059 (1) | 0.062 (1) | −0.002 (1) | 0.001 (1) | −0.013 (1) |
C7 | 0.062 (1) | 0.063 (1) | 0.099 (1) | −0.011 (1) | 0.005 (1) | −0.018 (1) |
C8 | 0.053 (1) | 0.063 (1) | 0.108 (1) | −0.006 (1) | 0.016 (1) | 0.007 (1) |
C9 | 0.056 (1) | 0.082 (1) | 0.067 (1) | −0.001 (1) | 0.014 (1) | 0.010 (1) |
C10 | 0.054 (1) | 0.066 (1) | 0.051 (1) | −0.005 (1) | 0.004 (1) | −0.003 (1) |
Geometric parameters (Å, º) top
N1—C3 | 1.412 (1) | C9—C10 | 1.382 (2) |
N1—C4 | 1.455 (2) | C1—H1 | 0.96 (1) |
C1—C2 | 1.383 (2) | N1—H1n | 0.87 (1) |
C1—C3i | 1.396 (2) | C2—H2 | 0.95 (1) |
C2—C3 | 1.387 (2) | C4—H4a | 0.96 (1) |
C3—C1i | 1.396 (2) | C4—H4b | 0.96 (1) |
C4—C5 | 1.511 (2) | C6—H6 | 0.97 (1) |
C5—C6 | 1.386 (2) | C7—H7 | 0.95 (1) |
C5—C10 | 1.393 (2) | C8—H8 | 0.96 (1) |
C6—C7 | 1.382 (2) | C9—H9 | 0.95 (1) |
C7—C8 | 1.370 (2) | C10—H10 | 0.96 (1) |
C8—C9 | 1.374 (2) | | |
| | | |
C3—N1—C4 | 121.9 (1) | C3i—C1—H1 | 120 (1) |
C2—C1—C3i | 120.6 (1) | C1—C2—H2 | 119 (1) |
C1—C2—C3 | 122.0 (1) | C3—C2—H2 | 119 (1) |
C2—C3—C1i | 117.4 (1) | N1—C4—H4a | 105 (1) |
C2—C3—N1 | 119.8 (1) | C5—C4—H4a | 109 (1) |
C1i—C3—N1 | 122.6 (1) | N1—C4—H4b | 108 (1) |
N1—C4—C5 | 115.8 (1) | C5—C4—H4b | 110 (1) |
C6—C5—C10 | 117.5 (1) | H4a—C4—H4b | 109 (1) |
C6—C5—C4 | 120.9 (1) | C7—C6—H6 | 120 (1) |
C10—C5—C4 | 121.6 (1) | C5—C6—H6 | 118 (1) |
C7—C6—C5 | 121.3 (1) | C8—C7—H7 | 120 (1) |
C8—C7—C6 | 120.3 (2) | C6—C7—H7 | 120 (1) |
C7—C8—C9 | 119.5 (2) | C7—C8—H8 | 121 (1) |
C8—C9—C10 | 120.3 (2) | C9—C8—H8 | 120 (1) |
C9—C10—C5 | 121.0 (1) | C8—C9—H9 | 121 (1) |
C3—N1—H1n | 112.5 (9) | C10—C9—H9 | 119 (1) |
C4—N1—H1n | 111.2 (9) | C9—C10—H10 | 121 (1) |
C2—C1—H1 | 119 (1) | C5—C10—H10 | 118 (1) |
| | | |
C3i—C1—C2—C3 | 0.0 (2) | C10—C5—C6—C7 | 0.6 (2) |
C1—C2—C3—C1i | 0.0 (2) | C4—C5—C6—C7 | −178.1 (1) |
C1—C2—C3—N1 | −174.7 (1) | C5—C6—C7—C8 | 0.7 (2) |
C4—N1—C3—C2 | −151.0 (1) | C6—C7—C8—C9 | −1.0 (3) |
C4—N1—C3—C1i | 34.5 (2) | C7—C8—C9—C10 | 0.0 (2) |
C3—N1—C4—C5 | 75.4 (2) | C8—C9—C10—C5 | 1.3 (2) |
N1—C4—C5—C6 | 119.5 (1) | C6—C5—C10—C9 | −1.6 (2) |
N1—C4—C5—C10 | −59.1 (2) | C4—C5—C10—C9 | 177.1 (1) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1n···N1ii | 0.87 (1) | 2.44 (1) | 3.281 (1) | 162 (1) |
Symmetry code: (ii) −x+1, y+1/2, −z+3/2. |
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