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The asymmetric unit of the title compound, C16H22N4, contains one half of the molecule, which lies on a crystallographic inversion center.
Supporting information
CCDC reference: 636629
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.002 Å
- R factor = 0.052
- wR factor = 0.167
- Data-to-parameter ratio = 16.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2A ... ?
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
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 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: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1997); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL-Plus.
N,
N'-Bis(2-aminobenzyl)ethane-1,2-diamine
top
Crystal data top
C16H22N4 | Dx = 1.241 Mg m−3 |
Mr = 270.38 | Melting point: 352.9 K |
Orthorhombic, Pccn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ab 2ac | Cell parameters from 76 reflections |
a = 9.974 (3) Å | θ = 4.7–13.5° |
b = 22.729 (7) Å | µ = 0.08 mm−1 |
c = 6.384 (2) Å | T = 298 K |
V = 1447.2 (8) Å3 | Prism, yellow |
Z = 4 | 0.60 × 0.60 × 0.45 mm |
F(000) = 584 | |
Data collection top
Bruker P4 diffractometer | Rint = 0.062 |
Radiation source: fine-focus sealed tube | θmax = 27.5°, θmin = 1.8° |
Graphite monochromator | h = −12→1 |
ω scans | k = −1→29 |
3702 measured reflections | l = −8→8 |
1661 independent reflections | 3 standard reflections every 97 reflections |
1191 reflections with I > 2σ(I) | intensity decay: 3% |
Refinement top
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)] = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.167 | w = 1/[σ2(Fo2) + (0.0954P)2 + 0.1803P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
1661 reflections | Δρmax = 0.25 e Å−3 |
104 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Extinction correction: SHELXTL-Plus, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.060 (14) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.68068 (17) | 0.42721 (6) | 0.4883 (2) | 0.0569 (4) | |
N2 | 0.50183 (14) | 0.42418 (6) | 0.11188 (19) | 0.0528 (4) | |
C1 | 0.59767 (14) | 0.38021 (6) | 0.5335 (2) | 0.0476 (4) | |
C2 | 0.63887 (16) | 0.33643 (7) | 0.6691 (2) | 0.0561 (5) | |
H2B | 0.7265 | 0.3365 | 0.7189 | 0.067* | |
C3 | 0.55305 (19) | 0.29297 (8) | 0.7312 (3) | 0.0649 (5) | |
H3A | 0.5821 | 0.2641 | 0.8238 | 0.078* | |
C4 | 0.42428 (19) | 0.29194 (8) | 0.6571 (3) | 0.0702 (6) | |
H4A | 0.3649 | 0.2629 | 0.7012 | 0.084* | |
C5 | 0.38385 (17) | 0.33392 (8) | 0.5179 (3) | 0.0617 (5) | |
H5A | 0.2969 | 0.3324 | 0.4654 | 0.074* | |
C6 | 0.46738 (14) | 0.37828 (7) | 0.4530 (2) | 0.0504 (4) | |
C7 | 0.42175 (15) | 0.42404 (7) | 0.3030 (3) | 0.0567 (5) | |
H7A | 0.3285 | 0.4170 | 0.2675 | 0.068* | |
H7B | 0.4277 | 0.4624 | 0.3693 | 0.068* | |
C8 | 0.46724 (16) | 0.47152 (7) | −0.0315 (2) | 0.0547 (5) | |
H8A | 0.3707 | 0.4766 | −0.0332 | 0.066* | |
H8B | 0.4956 | 0.4611 | −0.1720 | 0.066* | |
H2A | 0.4895 (19) | 0.3882 (9) | 0.047 (3) | 0.062 (5)* | |
H1A | 0.766 (2) | 0.4226 (8) | 0.520 (3) | 0.066 (5)* | |
H1B | 0.666 (2) | 0.4429 (9) | 0.359 (4) | 0.080 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0551 (9) | 0.0630 (8) | 0.0526 (8) | −0.0077 (6) | −0.0013 (7) | −0.0029 (6) |
N2 | 0.0577 (8) | 0.0556 (8) | 0.0451 (7) | 0.0106 (6) | −0.0008 (6) | −0.0067 (5) |
C1 | 0.0495 (8) | 0.0538 (8) | 0.0394 (7) | −0.0019 (6) | 0.0049 (6) | −0.0099 (6) |
C2 | 0.0596 (9) | 0.0649 (9) | 0.0438 (7) | −0.0004 (7) | −0.0029 (7) | −0.0049 (7) |
C3 | 0.0780 (11) | 0.0661 (10) | 0.0506 (8) | 0.0000 (8) | 0.0055 (9) | 0.0049 (7) |
C4 | 0.0702 (11) | 0.0703 (11) | 0.0700 (11) | −0.0126 (9) | 0.0150 (9) | 0.0044 (9) |
C5 | 0.0490 (8) | 0.0740 (10) | 0.0622 (9) | −0.0057 (8) | 0.0057 (7) | −0.0104 (8) |
C6 | 0.0486 (8) | 0.0578 (9) | 0.0448 (7) | 0.0028 (6) | 0.0056 (6) | −0.0106 (6) |
C7 | 0.0495 (8) | 0.0657 (10) | 0.0550 (9) | 0.0092 (7) | 0.0028 (7) | −0.0080 (7) |
C8 | 0.0576 (9) | 0.0593 (9) | 0.0472 (8) | 0.0088 (7) | −0.0109 (7) | −0.0066 (7) |
Geometric parameters (Å, º) top
N1—C1 | 1.382 (2) | C3—H3A | 0.9300 |
N1—H1A | 0.88 (2) | C4—C5 | 1.365 (3) |
N1—H1B | 0.91 (2) | C4—H4A | 0.9300 |
N2—C8 | 1.454 (2) | C5—C6 | 1.372 (2) |
N2—C7 | 1.459 (2) | C5—H5A | 0.9300 |
N2—H2A | 0.924 (19) | C6—C7 | 1.485 (2) |
C1—C2 | 1.381 (2) | C7—H7A | 0.9700 |
C1—C6 | 1.398 (2) | C7—H7B | 0.9700 |
C2—C3 | 1.366 (2) | C8—C8i | 1.505 (3) |
C2—H2B | 0.9300 | C8—H8A | 0.9700 |
C3—C4 | 1.369 (3) | C8—H8B | 0.9700 |
| | | |
C1—N1—H1A | 116.1 (12) | C4—C5—C6 | 122.08 (16) |
C1—N1—H1B | 113.4 (13) | C4—C5—H5A | 119.0 |
H1A—N1—H1B | 114.2 (18) | C6—C5—H5A | 119.0 |
C8—N2—C7 | 113.47 (12) | C5—C6—C1 | 118.44 (15) |
C8—N2—H2A | 109.9 (11) | C5—C6—C7 | 121.56 (15) |
C7—N2—H2A | 107.5 (11) | C1—C6—C7 | 120.00 (14) |
C2—C1—N1 | 120.64 (15) | N2—C7—C6 | 111.90 (12) |
C2—C1—C6 | 118.96 (14) | N2—C7—H7A | 109.2 |
N1—C1—C6 | 120.27 (15) | C6—C7—H7A | 109.2 |
C3—C2—C1 | 121.10 (16) | N2—C7—H7B | 109.2 |
C3—C2—H2B | 119.5 | C6—C7—H7B | 109.2 |
C1—C2—H2B | 119.5 | H7A—C7—H7B | 107.9 |
C2—C3—C4 | 120.00 (17) | N2—C8—C8i | 111.43 (15) |
C2—C3—H3A | 120.0 | N2—C8—H8A | 109.3 |
C4—C3—H3A | 120.0 | C8i—C8—H8A | 109.3 |
C5—C4—C3 | 119.35 (16) | N2—C8—H8B | 109.3 |
C5—C4—H4A | 120.3 | C8i—C8—H8B | 109.3 |
C3—C4—H4A | 120.3 | H8A—C8—H8B | 108.0 |
| | | |
N1—C1—C2—C3 | 173.39 (14) | N1—C1—C6—C5 | −173.71 (13) |
C6—C1—C2—C3 | −2.6 (2) | C2—C1—C6—C7 | −178.54 (13) |
C1—C2—C3—C4 | 0.7 (3) | N1—C1—C6—C7 | 5.5 (2) |
C2—C3—C4—C5 | 1.4 (3) | C8—N2—C7—C6 | −175.26 (13) |
C3—C4—C5—C6 | −1.6 (3) | C5—C6—C7—N2 | −119.70 (16) |
C4—C5—C6—C1 | −0.2 (2) | C1—C6—C7—N2 | 61.15 (18) |
C4—C5—C6—C7 | −179.38 (16) | C7—N2—C8—C8i | 81.3 (2) |
C2—C1—C6—C5 | 2.3 (2) | | |
Symmetry code: (i) −x+1, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···N2 | 0.91 (2) | 2.32 (2) | 2.994 (2) | 131.3 (17) |
N1—H1A···N2ii | 0.88 (2) | 2.39 (2) | 3.264 (2) | 172.3 (16) |
Symmetry code: (ii) −x+3/2, y, z+1/2. |
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