N,N'-Bis(2-amino­benz­yl)ethane-1,2-diamine

The asymmetric unit of the title compound, C₁₆H₂₂N₄, contains one half of the mol­ecule, which lies on a crystallographic inversion center.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3	Prism, yellow
Z = 4	0.60 × 0.60 × 0.45 mm
F(000) = 584

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.167	w = 1/[σ^2(Fo^2) + (0.0954P)^2 + 0.1803P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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—C8^i	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—C8^i	111.43 (15)
C2—C3—H3A	120.0	N2—C8—H8A	109.3
C4—C3—H3A	120.0	C8^i—C8—H8A	109.3
C5—C4—C3	119.35 (16)	N2—C8—H8B	109.3
C5—C4—H4A	120.3	C8^i—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—C8^i	81.3 (2)
C2—C1—C6—C5	2.3 (2)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º)

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···N2^ii	0.88 (2)	2.39 (2)	3.264 (2)	172.3 (16)

Symmetry code: (ii) −x+3/2, y, z+1/2.