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The title compound, [N(CH2CH2NH3)3]Br3, is a salt of a triprotonated tetr­amine. The tertiary amine N atom sits on a threefold axis, as do the three bromide anions. Each of the primary amines is protonated, while the tertiary amine is not protonated. The compound is isostructural with the chloride and the perchlorate analogs.

Supporting information


Crystallographic Information File (CIF)
Contains datablocks General, I


Structure factor file (CIF format)
Contains datablock I

CCDC reference: 226935

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.063
  • wR factor = 0.145
  • Data-to-parameter ratio = 33.4

checkCIF/PLATON results

No syntax errors found

Alert level A PLAT035_ALERT_1_A No _chemical_absolute_configuration info given . ?
Author Response: ...see _publ_section_exptl_refinement.

Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR) is > 1.50 Tmin and Tmax reported: 0.164 0.218 Tmin and Tmax expected: 0.107 0.217 RR = 1.529 Please check that your absorption correction is appropriate. PLAT060_ALERT_3_B Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.52
Alert level C CRYSC01_ALERT_1_C The word below has not been recognised as a standard identifier. tan CRYSC01_ALERT_1_C No recognised colour has been given for crystal colour. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 Br
Alert level G REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 35.54 From the CIF: _reflns_number_total 1598 From the CIF: _diffrn_reflns_limit_ max hkl 18. 12. 12. From the CIF: _diffrn_reflns_limit_ min hkl -18. -12. -12. TEST1: Expected hkl limits for theta max Calculated maximum hkl 18. 18. 18. Calculated minimum hkl -18. -18. -18. REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 35.54 From the CIF: _reflns_number_total 1598 Count of symmetry unique reflns 1166 Completeness (_total/calc) 137.05% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 432 Fraction of Friedel pairs measured 0.370 Are heavy atom types Z>Si present yes
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 5 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 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: COLLECT (Nonius 2000); cell refinement: DENZO and SCALEPACK version 1.96.2 (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK version 1.96.2 (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare, et al. 1993); program(s) used to refine structure: TEXSAN for Windows version 1.06 (MSC, 1997-1999); software used to prepare material for publication: TEXSAN for Windows version 1.06 (MSC, 1997-1999).

(I) top
Crystal data top
C6H21N4·3(Br)Dx = 1.921 Mg m3
Mr = 388.97Mo Kα radiation, λ = 0.7107 Å
Cubic, P213Cell parameters from 1167 reflections
Hall symbol: P 2ac 2ab 3θ = 2.5–35.5°
a = 11.038 (2) ŵ = 9.00 mm1
V = 1344.8 (4) Å3T = 100 K
Z = 4Fragment, tan
F(000) = 760.00.27 × 0.22 × 0.17 mm
Data collection top
KappaCCD (with Oxford Cryostream)
1598 independent reflections
Radiation source: fine-focus sealed tube1335 reflections with I > 3.00σ(I)
Graphite monochromatorRint = 0.042
ω scans with κ offsetsθmax = 35.5°, θmin = 2.6°
Absorption correction: multi-scan
HKL Scalepack (Otwinowski & Minor 1997)
h = 1818
Tmin = 0.164, Tmax = 0.218k = 1212
14942 measured reflectionsl = 1212
Refinement top
Refinement on F20 restraints
Least-squares matrix: full24 constraints
R[F2 > 2σ(F2)] = 0.063H-atom parameters not refined
wR(F2) = 0.145Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo) + 0.00331|Fo|2]
S = 1.09(Δ/σ)max = 0.0002
1335 reflectionsΔρmax = 0.73 e Å3
40 parametersΔρmin = 1.36 e Å3
Special details top

Refinement. Refinement of F2. The weighted R-factor wR and goodness of fit are based on F2, conventional R-factors R are based on F. R-factors based on F2 are statistically about twice as large as those based on F.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
Br10.17771 (5)0.17770.17770.01888 (4)
Br20.30081 (5)0.30080.30080.01720 (4)
Br30.54581 (4)0.54580.54580.01311 (4)
N10.0404 (4)0.0139 (5)0.2475 (4)0.0186 (9)
N20.0252 (4)0.02520.02520.0087 (2)
C10.1445 (4)0.0401 (5)0.1640 (4)0.0128 (9)
C20.1009 (4)0.1038 (4)0.0508 (5)0.0132 (8)
Atomic displacement parameters (Å2) top
Br10.0189 (2)0.01890.01890.0036 (2)0.00360.0036
Br20.0171 (2)0.01710.01710.0016 (5)0.00160.0016
Br30.0131 (2)0.01310.01310.0047 (5)0.00470.0047
N10.016 (2)0.028 (2)0.013 (2)0.001 (2)0.001 (1)0.001 (2)
N20.0087 (10)0.00870.00870.0006 (10)0.00060.0006
C10.011 (2)0.014 (2)0.012 (2)0.001 (1)0.0016 (13)0.000 (1)
C20.013 (2)0.008 (2)0.019 (2)0.0016 (13)0.003 (2)0.000 (1)
Geometric parameters (Å, º) top
N1—C11.501 (6)N2—C2ii1.468 (5)
N1—H10.95C1—C21.512 (7)
N2—C21.468 (5)C2—H60.95
N2—C2i1.468 (5)C2—H70.95
BR1···N13.296 (5)BR2···H3iv2.805
BR1···H12.542BR3···N1iv3.359 (4)
BR1···C1iii3.590 (5)BR3···H2iv2.762
BR2···N1iv3.395 (5)
C2—N2—C2i109.1 (3)N1—C1—H4109.17
C2—N2—C2ii109.1 (3)N1—C1—H5109.17
C2i—N2—C2ii109.1 (3)C2—C1—H4109.17
N1—C1—C2110.7 (4)C2—C1—H5109.17
N2—C2—C1112.3 (4)H4—C1—H5109.46
N1—C1—C2—N267.4 (5)C1—C2—N2—C2ii82.9 (6)
C1—C2—N2—C2i158.0 (4)
Symmetry codes: (i) z, x, y; (ii) y, z, x; (iii) y1/2, z1/2, x; (iv) x+1/2, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
N1—H1···Br10.952.543.296 (5)136
N1—H2···Br3v0.952.763.359 (4)122
N1—H3···Br2v0.952.813.395 (5)121
Symmetry code: (v) x1/2, y+1/2, z.

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