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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806030819/hg2087sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806030819/hg2087Isup2.hkl
Contains datablock I

CCDC reference: 621347

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](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

Computing details top

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
C20H20N2F(000) = 308
Mr = 288.38Dx = 1.222 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1867 reflections
a = 11.912 (1) Åθ = 3.4–26.3°
b = 5.5402 (8) ŵ = 0.07 mm1
c = 11.895 (1) ÅT = 295 K
β = 93.47 (1)°Plate, colorless
V = 783.5 (2) Å30.44 × 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 tubeRint = 0.020
Graphite monochromatorθmax = 27.5°, θmin = 3.4°
φ and ω scansh = 1515
6428 measured reflectionsk = 77
1800 independent reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: difference Fourier map
wR(F2) = 0.105All 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 parametersΔρmax = 0.12 e Å3
10 restraintsΔρmin = 0.15 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.5592 (1)0.7203 (2)0.7094 (1)0.0474 (3)
C10.4150 (1)0.5994 (2)0.4306 (1)0.0430 (3)
C20.4490 (1)0.7087 (2)0.5316 (1)0.0423 (3)
C30.5340 (1)0.6133 (2)0.6031 (1)0.0386 (3)
C40.6716 (1)0.7110 (2)0.7644 (1)0.0486 (3)
C50.7573 (1)0.8780 (2)0.7172 (1)0.0451 (3)
C60.8099 (1)1.0548 (3)0.7838 (1)0.0595 (4)
C70.8860 (1)1.2128 (3)0.7406 (2)0.0747 (5)
C80.9102 (1)1.1992 (3)0.6296 (2)0.0740 (5)
C90.8596 (1)1.0248 (3)0.5619 (1)0.0678 (4)
C100.7847 (1)0.8640 (3)0.6052 (1)0.0567 (3)
H1n0.530 (1)0.864 (2)0.715 (1)0.057 (4)*
H10.355 (1)0.672 (2)0.384 (1)0.054 (3)*
H20.413 (1)0.852 (2)0.553 (1)0.052 (3)*
H4a0.662 (1)0.754 (2)0.842 (1)0.061 (4)*
H4b0.697 (1)0.546 (2)0.761 (1)0.059 (4)*
H60.792 (1)1.066 (3)0.862 (1)0.075 (5)*
H70.922 (2)1.332 (3)0.788 (1)0.099 (6)*
H80.962 (1)1.310 (3)0.599 (1)0.089 (5)*
H90.875 (1)1.012 (3)0.485 (1)0.088 (5)*
H100.750 (1)0.739 (2)0.559 (1)0.067 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.051 (1)0.049 (1)0.043 (1)0.001 (1)0.006 (1)0.011 (1)
C10.046 (1)0.040 (1)0.043 (1)0.005 (1)0.003 (1)0.001 (1)
C20.049 (1)0.033 (1)0.046 (1)0.004 (1)0.011 (1)0.003 (1)
C30.043 (1)0.037 (1)0.037 (1)0.005 (1)0.010 (1)0.002 (1)
C40.060 (1)0.049 (1)0.036 (1)0.001 (1)0.000 (1)0.001 (1)
C50.043 (1)0.045 (1)0.047 (1)0.006 (1)0.002 (1)0.001 (1)
C60.057 (1)0.059 (1)0.062 (1)0.002 (1)0.001 (1)0.013 (1)
C70.062 (1)0.063 (1)0.099 (1)0.011 (1)0.005 (1)0.018 (1)
C80.053 (1)0.063 (1)0.108 (1)0.006 (1)0.016 (1)0.007 (1)
C90.056 (1)0.082 (1)0.067 (1)0.001 (1)0.014 (1)0.010 (1)
C100.054 (1)0.066 (1)0.051 (1)0.005 (1)0.004 (1)0.003 (1)
Geometric parameters (Å, º) top
N1—C31.412 (1)C9—C101.382 (2)
N1—C41.455 (2)C1—H10.96 (1)
C1—C21.383 (2)N1—H1n0.87 (1)
C1—C3i1.396 (2)C2—H20.95 (1)
C2—C31.387 (2)C4—H4a0.96 (1)
C3—C1i1.396 (2)C4—H4b0.96 (1)
C4—C51.511 (2)C6—H60.97 (1)
C5—C61.386 (2)C7—H70.95 (1)
C5—C101.393 (2)C8—H80.96 (1)
C6—C71.382 (2)C9—H90.95 (1)
C7—C81.370 (2)C10—H100.96 (1)
C8—C91.374 (2)
C3—N1—C4121.9 (1)C3i—C1—H1120 (1)
C2—C1—C3i120.6 (1)C1—C2—H2119 (1)
C1—C2—C3122.0 (1)C3—C2—H2119 (1)
C2—C3—C1i117.4 (1)N1—C4—H4a105 (1)
C2—C3—N1119.8 (1)C5—C4—H4a109 (1)
C1i—C3—N1122.6 (1)N1—C4—H4b108 (1)
N1—C4—C5115.8 (1)C5—C4—H4b110 (1)
C6—C5—C10117.5 (1)H4a—C4—H4b109 (1)
C6—C5—C4120.9 (1)C7—C6—H6120 (1)
C10—C5—C4121.6 (1)C5—C6—H6118 (1)
C7—C6—C5121.3 (1)C8—C7—H7120 (1)
C8—C7—C6120.3 (2)C6—C7—H7120 (1)
C7—C8—C9119.5 (2)C7—C8—H8121 (1)
C8—C9—C10120.3 (2)C9—C8—H8120 (1)
C9—C10—C5121.0 (1)C8—C9—H9121 (1)
C3—N1—H1n112.5 (9)C10—C9—H9119 (1)
C4—N1—H1n111.2 (9)C9—C10—H10121 (1)
C2—C1—H1119 (1)C5—C10—H10118 (1)
C3i—C1—C2—C30.0 (2)C10—C5—C6—C70.6 (2)
C1—C2—C3—C1i0.0 (2)C4—C5—C6—C7178.1 (1)
C1—C2—C3—N1174.7 (1)C5—C6—C7—C80.7 (2)
C4—N1—C3—C2151.0 (1)C6—C7—C8—C91.0 (3)
C4—N1—C3—C1i34.5 (2)C7—C8—C9—C100.0 (2)
C3—N1—C4—C575.4 (2)C8—C9—C10—C51.3 (2)
N1—C4—C5—C6119.5 (1)C6—C5—C10—C91.6 (2)
N1—C4—C5—C1059.1 (2)C4—C5—C10—C9177.1 (1)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1n···N1ii0.87 (1)2.44 (1)3.281 (1)162 (1)
Symmetry code: (ii) x+1, y+1/2, z+3/2.
 

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