Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The penta­dentate ligand TRENEN [4-(2-aminoet­yl)-1,4,7,10-tetra­azadeca­ne] is not readily available in the pure state, but is present as a major impurity in commercial tetra­ethyl­ene penta­mine. Therefore, only four structures containing TRENEN have been reported previously. We report here the crystal structure of the title compound, [Li(trenen)]Cl or [Li(C8H23N5)]Cl. The Li atom has a distorted trigonal–bipyramidal coordination geometry. The [Li(trenen)]+ cation is chiral since one of the N atoms is a chirogenic centre. A second type of chirality arises as a consequence of the chelate-ring conformations. In the racemic crystal structure, mol­ecules assemble into bilayers via N—H...Cl inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806047593/ng2150sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806047593/ng2150Isup2.hkl
Contains datablock I

CCDC reference: 630187

Key indicators

  • Single-crystal X-ray study
  • T = 303 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.036
  • wR factor = 0.077
  • Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT420_ALERT_2_C D-H Without Acceptor N1 - H10 ... ? PLAT420_ALERT_2_C D-H Without Acceptor N4 - H12 ... ? PLAT420_ALERT_2_C D-H Without Acceptor N5 - H15 ... ? PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 Cl
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 3 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

[4-(2-Aminoethyl)-1,4,7,10-tetraazadecane]lithium chloride top
Crystal data top
[Li(C8H23N5)]ClF(000) = 504
Mr = 231.70Dx = 1.191 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8324 reflections
a = 12.079 (9) Åθ = 3.0–25.5°
b = 7.914 (5) ŵ = 0.27 mm1
c = 13.559 (10) ÅT = 303 K
β = 94.48 (3)°Prism, colourless
V = 1292.2 (16) Å30.15 × 0.10 × 0.10 mm
Z = 4
Data collection top
Rigaku R-AXIS IIc image-plate system
diffractometer
2170 reflections with I > 2σ(I)
Radiation source: rotating-anode X-ray tube, Rigaku RU-H3RRint = 0.034
Graphite monochromatorθmax = 25.5°, θmin = 3.0°
Detector resolution: 105 pixels mm-1h = 1314
φ scansk = 99
8324 measured reflectionsl = 1616
2386 independent reflections
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.0234P)2 + 0.8724P]
where P = (Fo2 + 2Fc2)/3
2386 reflections(Δ/σ)max = 0.001
164 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.22 e Å3
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
xyzUiso*/Ueq
C10.00724 (13)0.2750 (2)0.59569 (12)0.0182 (3)
H1A0.02220.35300.54500.022*
H1B0.04760.18730.60300.022*
C20.11396 (13)0.1968 (2)0.56514 (12)0.0167 (3)
H2B0.14120.11470.61430.020*
H2A0.09970.13870.50250.020*
C30.31350 (12)0.27008 (19)0.56960 (11)0.0141 (3)
H3A0.33010.19580.51580.017*
H3B0.32510.20780.63120.017*
C40.38905 (12)0.42409 (19)0.57200 (11)0.0145 (3)
H4B0.46590.38820.58170.017*
H4A0.37920.48310.50920.017*
C50.42644 (13)0.4980 (2)0.74639 (11)0.0160 (3)
H5A0.49810.55370.74890.019*
H5B0.43920.37710.74990.019*
C60.36486 (13)0.5533 (2)0.83450 (11)0.0179 (3)
H6B0.40550.51780.89550.021*
H6A0.35850.67550.83530.021*
C80.26365 (13)0.77565 (19)0.56771 (11)0.0156 (3)
H8B0.26950.89370.54950.019*
H8A0.25100.70970.50760.019*
C70.37017 (13)0.71836 (19)0.62518 (11)0.0150 (3)
H7A0.43230.73510.58510.018*
H7B0.38290.78620.68460.018*
N10.02939 (12)0.3655 (2)0.69003 (10)0.0192 (3)
N20.19777 (10)0.32792 (16)0.55556 (10)0.0127 (3)
N30.36348 (10)0.53899 (16)0.65252 (9)0.0120 (3)
N40.25387 (12)0.4767 (2)0.82674 (10)0.0180 (3)
N50.17037 (11)0.75233 (17)0.63072 (10)0.0154 (3)
Li10.1824 (2)0.5004 (3)0.67806 (19)0.0154 (5)
Cl10.22911 (3)0.54135 (5)0.68048 (3)0.01946 (12)
H120.2132 (17)0.514 (3)0.8737 (16)0.032 (6)*
H130.2613 (18)0.366 (3)0.8348 (16)0.037 (6)*
H150.1059 (17)0.785 (3)0.5967 (15)0.025 (5)*
H140.1802 (17)0.824 (3)0.6801 (16)0.028 (5)*
H110.1889 (16)0.373 (3)0.4945 (15)0.026 (5)*
H100.0475 (17)0.290 (3)0.7367 (17)0.032 (6)*
H90.0333 (19)0.415 (3)0.7045 (15)0.031 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0150 (8)0.0184 (8)0.0208 (8)0.0060 (6)0.0013 (6)0.0001 (7)
C20.0203 (8)0.0125 (7)0.0172 (8)0.0039 (6)0.0008 (6)0.0021 (6)
C30.0168 (8)0.0122 (7)0.0135 (7)0.0019 (6)0.0022 (6)0.0019 (6)
C40.0134 (7)0.0155 (8)0.0152 (7)0.0012 (6)0.0043 (6)0.0008 (6)
C50.0137 (7)0.0161 (8)0.0173 (8)0.0002 (6)0.0036 (6)0.0015 (6)
C60.0220 (8)0.0178 (8)0.0129 (7)0.0020 (7)0.0045 (6)0.0005 (6)
C80.0226 (8)0.0107 (7)0.0132 (7)0.0002 (6)0.0002 (6)0.0012 (6)
C70.0165 (8)0.0123 (7)0.0161 (8)0.0047 (6)0.0013 (6)0.0005 (6)
N10.0163 (7)0.0229 (7)0.0188 (7)0.0011 (6)0.0036 (5)0.0004 (6)
N20.0138 (7)0.0121 (6)0.0121 (6)0.0017 (5)0.0007 (5)0.0011 (5)
N30.0141 (6)0.0108 (6)0.0108 (6)0.0002 (5)0.0005 (5)0.0006 (5)
N40.0208 (7)0.0202 (8)0.0134 (7)0.0012 (6)0.0036 (5)0.0002 (6)
N50.0158 (7)0.0142 (7)0.0156 (7)0.0017 (5)0.0017 (5)0.0022 (6)
Li10.0154 (12)0.0159 (13)0.0149 (12)0.0004 (10)0.0007 (10)0.0002 (10)
Cl10.0267 (2)0.0190 (2)0.01255 (19)0.00515 (16)0.00072 (14)0.00212 (15)
Geometric parameters (Å, º) top
C1—N11.472 (2)C6—H6A0.9700
C1—C21.517 (2)C8—N51.478 (2)
C1—H1A0.9700C8—C71.520 (2)
C1—H1B0.9700C8—H8B0.9700
C2—N21.462 (2)C8—H8A0.9700
C2—H2B0.9700C7—N31.471 (2)
C2—H2A0.9700C7—H7A0.9700
C3—N21.469 (2)C7—H7B0.9700
C3—C41.521 (2)N1—Li12.151 (3)
C3—H3A0.9700N1—H100.88 (2)
C3—H3B0.9700N1—H90.89 (2)
C4—N31.472 (2)N2—Li12.169 (3)
C4—H4B0.9700N2—H110.90 (2)
C4—H4A0.9700N3—Li12.262 (3)
C5—N31.467 (2)N4—Li12.139 (3)
C5—C61.520 (2)N4—H120.89 (2)
C5—H5A0.9700N4—H130.89 (2)
C5—H5B0.9700N5—Li12.096 (3)
C6—N41.468 (2)N5—H150.91 (2)
C6—H6B0.9700N5—H140.88 (2)
N1—C1—C2109.58 (13)C8—C7—H7A109.5
N1—C1—H1A109.8N3—C7—H7B109.5
C2—C1—H1A109.8C8—C7—H7B109.5
N1—C1—H1B109.8H7A—C7—H7B108.1
C2—C1—H1B109.8C1—N1—Li1105.95 (12)
H1A—C1—H1B108.2C1—N1—H10108.2 (14)
N2—C2—C1110.11 (14)Li1—N1—H10102.9 (14)
N2—C2—H2B109.6C1—N1—H9107.8 (13)
C1—C2—H2B109.6Li1—N1—H9123.4 (14)
N2—C2—H2A109.6H10—N1—H9107.9 (18)
C1—C2—H2A109.6C2—N2—C3115.20 (13)
H2B—C2—H2A108.2C2—N2—Li1106.08 (12)
N2—C3—C4108.44 (13)C3—N2—Li1103.57 (11)
N2—C3—H3A110.0C2—N2—H11109.1 (13)
C4—C3—H3A110.0C3—N2—H11106.6 (12)
N2—C3—H3B110.0Li1—N2—H11116.5 (13)
C4—C3—H3B110.0C5—N3—C7113.40 (12)
H3A—C3—H3B108.4C5—N3—C4112.47 (13)
N3—C4—C3110.52 (12)C7—N3—C4112.98 (12)
N3—C4—H4B109.5C5—N3—Li1106.22 (12)
C3—C4—H4B109.5C7—N3—Li1103.99 (11)
N3—C4—H4A109.5C4—N3—Li1106.95 (11)
C3—C4—H4A109.5C6—N4—Li1109.32 (12)
H4B—C4—H4A108.1C6—N4—H12111.4 (14)
N3—C5—C6111.45 (13)Li1—N4—H12116.3 (13)
N3—C5—H5A109.3C6—N4—H13108.4 (14)
C6—C5—H5A109.3Li1—N4—H13103.4 (14)
N3—C5—H5B109.3H12—N4—H13107 (2)
C6—C5—H5B109.3C8—N5—Li1104.97 (12)
H5A—C5—H5B108.0C8—N5—H15109.5 (12)
N4—C6—C5108.95 (13)Li1—N5—H15117.3 (13)
N4—C6—H6B109.9C8—N5—H14107.3 (13)
C5—C6—H6B109.9Li1—N5—H14112.2 (13)
N4—C6—H6A109.9H15—N5—H14105.3 (18)
C5—C6—H6A109.9N5—Li1—N4112.66 (13)
H6B—C6—H6A108.3N5—Li1—N1117.13 (14)
N5—C8—C7108.63 (13)N4—Li1—N199.87 (12)
N5—C8—H8B110.0N5—Li1—N2111.84 (13)
C7—C8—H8B110.0N4—Li1—N2127.89 (14)
N5—C8—H8A110.0N1—Li1—N282.59 (11)
C7—C8—H8A110.0N5—Li1—N382.48 (10)
H8B—C8—H8A108.3N4—Li1—N380.32 (11)
N3—C7—C8110.85 (12)N1—Li1—N3157.70 (14)
N3—C7—H7A109.5N2—Li1—N379.97 (10)
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds