Four-centre hydrogen bonds: a triethano­lamine-triethano­lamine oxide complex

The title complex, ((HOCH₂CH₂)₃N)(HOCH₂CH₂)₃NO) or C₆H₁₅NO₄·C₆H₁₅NO₃, has the amine-oxide O atom trifurcated by a trigonal `cap' of hydrogen bonds to the hydroxyl H atoms of the triethano­lamine lying on the same threefold axis. The amine-oxide hydroxyl H atoms are hydrogen bonded to three adjacent triethano­lamine O atoms, completing a three-dimensional polymeric network.

Key indicators

• Single-crystal X-ray study
• T = 168 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.061
• wR factor = 0.134
• Data-to-parameter ratio = 6.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level A:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           26.40
         From the CIF: _reflns_number_total                422
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns          558
         Completeness (_total/calc)             75.63%
          Alert A: < 85% complete (theta max?)

Author response: ... An incomplete triclinic data set was obtained before icing stopped the data collection and (then) the crystal decomposed.

RINTA_01  Alert A The value of Rint is greater than 0.20
          Rint given   0.211

Author response: The crystals were weak diffractors but the only ones available; attempts at re-sythesis were unsuccessful. Determination of the lattice indicated non-systematic twinning/multiple crystal effects.

 Alert Level C:



PLAT_031  Alert C Refined Extinction parameter within range ....       3.20 Sigma

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           26.40
         From the CIF: _reflns_number_total                422
         From the CIF: _diffrn_reflns_limit_ max hkl   13.   13.    9.
         From the CIF: _diffrn_reflns_limit_ min hkl  -14.  -15.   -8.
         TEST1: Expected hkl limits for theta max
         Calculated maximum hkl   15.   15.   12.
         Calculated minimum hkl  -15.  -15.  -12.
          ALERT: Expected hkl max differ from CIF values

REFLT_03
         From the CIF: _diffrn_reflns_theta_max           26.40
         From the CIF: _reflns_number_total                422
         Count of symmetry unique reflns          558
         Completeness (_total/calc)             75.63%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.


 2 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996) and SADABS (Sheldrick, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 in WinGX (Farrugia, 1997, 1999); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

C6H15NO4·C6H15NO3	Dx = 1.290 Mg m^−3
Mr = 314.38	Mo Kα radiation, λ = 0.71073 Å
Hexagonal, R3	Cell parameters from 330 reflections
Hall symbol: R 3	θ = 2.9–21.9°
a = 12.065 (5) Å	µ = 0.11 mm^−1
c = 9.633 (8) Å	T = 168 K
V = 1214.4 (13) Å^3	Plate, colourless
Z = 3	0.29 × 0.20 × 0.02 mm
F(000) = 516

Data collection

Bruker P4 diffractometer	299 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.211
Graphite monochromator	θmax = 26.4°, θmin = 2.9°
Detector resolution: 8.192 pixels mm^-1	h = −14→13
ω scans	k = −15→13
1170 measured reflections	l = −8→9
422 independent reflections

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)] = 0.061	H-atom parameters constrained
wR(F^2) = 0.134	w = 1/[σ^2(Fo^2) + (0.038P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
422 reflections	Δρmax = 0.24 e Å^−3
67 parameters	Δρmin = −0.30 e Å^−3
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.016 (5)

Special details

Experimental. Crystal decay was monitored by repeating the initial 10 frames at the end of the data collection (shell) and analyzing duplicate reflections. The standard 0.8 mm diameter collimator was used.

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. Friedel equivalent reflections were merged, as the data accuracy and size of anomalous fdispersion terms precluded assigned absolute configuration. 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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.5187 (4)	0.6472 (4)	0.2379 (5)	0.0403 (14)
H1	0.4548	0.6472	0.2034	0.048*
N1	0.3333	0.6667	0.4263 (10)	0.038 (3)
C1	0.4526 (6)	0.6704 (7)	0.4715 (8)	0.0421 (19)
H11	0.4409	0.6354	0.5667	0.051*
H12	0.5232	0.7604	0.4738	0.051*
C2	0.4881 (6)	0.5946 (7)	0.3762 (7)	0.043 (2)
H21	0.5628	0.5923	0.4152	0.052*
H22	0.4160	0.5055	0.3713	0.052*
O2	0.0531 (4)	0.5365 (4)	−0.1812 (5)	0.0504 (16)
H2	−0.0090	0.4685	−0.1507	0.060*
O3	0.3333	0.6667	0.1011 (9)	0.0311 (19)
N11	0.3333	0.6667	−0.0466 (11)	0.031 (2)
C11	0.2474 (5)	0.7159 (6)	−0.0962 (7)	0.0342 (18)
H111	0.2617	0.7333	−0.1970	0.041*
H112	0.2738	0.7985	−0.0494	0.041*
C21	0.1052 (6)	0.6285 (6)	−0.0723 (7)	0.0419 (17)
H211	0.0910	0.5844	0.0181	0.050*
H212	0.0617	0.6797	−0.0700	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.042 (2)	0.056 (3)	0.026 (4)	0.027 (2)	−0.006 (2)	−0.001 (2)
N1	0.040 (3)	0.040 (3)	0.034 (7)	0.0201 (15)	0.000	0.000
C1	0.051 (4)	0.054 (4)	0.026 (6)	0.030 (3)	−0.006 (3)	−0.003 (3)
C2	0.043 (4)	0.048 (4)	0.040 (7)	0.025 (3)	−0.006 (3)	−0.002 (4)
O2	0.037 (3)	0.057 (3)	0.044 (4)	0.013 (2)	−0.004 (2)	−0.006 (3)
O3	0.037 (2)	0.037 (2)	0.020 (6)	0.0183 (12)	0.000	0.000
N11	0.038 (3)	0.038 (3)	0.017 (8)	0.0192 (16)	0.000	0.000
C11	0.037 (3)	0.039 (3)	0.030 (5)	0.021 (3)	0.003 (3)	0.005 (3)
C21	0.037 (3)	0.043 (4)	0.049 (5)	0.022 (3)	−0.001 (3)	0.000 (3)

Geometric parameters (Å, º)

O1—C2	1.441 (8)	O2—H2	0.8400
O1—H1	0.8400	O3—N11	1.422 (12)
N1—C1^i	1.482 (7)	N11—C11	1.508 (6)
N1—C1^ii	1.482 (7)	N11—C11^ii	1.508 (6)
N1—C1	1.482 (7)	N11—C11^i	1.508 (6)
C1—C2	1.502 (10)	C11—C21	1.516 (9)
C1—H11	0.9900	C11—H111	0.9900
C1—H12	0.9900	C11—H112	0.9900
C2—H21	0.9900	C21—H211	0.9900
C2—H22	0.9900	C21—H212	0.9900
O2—C21	1.426 (8)
C2—O1—H1	109.5	O3—N11—C11^ii	108.5 (5)
C1^i—N1—C1^ii	111.8 (4)	C11—N11—C11^ii	110.4 (4)
C1^i—N1—C1	111.8 (4)	O3—N11—C11^i	108.5 (5)
C1^ii—N1—C1	111.8 (4)	C11—N11—C11^i	110.4 (4)
N1—C1—C2	111.7 (6)	C11^ii—N11—C11^i	110.4 (4)
N1—C1—H11	109.3	N11—C11—C21	116.1 (5)
C2—C1—H11	109.3	N11—C11—H111	108.3
N1—C1—H12	109.3	C21—C11—H111	108.3
C2—C1—H12	109.3	N11—C11—H112	108.3
H11—C1—H12	107.9	C21—C11—H112	108.3
O1—C2—C1	112.7 (6)	H111—C11—H112	107.4
O1—C2—H21	109.1	O2—C21—C11	109.5 (6)
C1—C2—H21	109.1	O2—C21—H211	109.8
O1—C2—H22	109.1	C11—C21—H211	109.8
C1—C2—H22	109.1	O2—C21—H212	109.8
H21—C2—H22	107.8	C11—C21—H212	109.8
C21—O2—H2	109.5	H211—C21—H212	108.2
O3—N11—C11	108.5 (5)
C1^i—N1—C1—C2	−152.7 (6)	C11^ii—N11—C11—C21	171.2 (5)
C1^ii—N1—C1—C2	81.1 (10)	C11^i—N11—C11—C21	48.8 (11)
N1—C1—C2—O1	64.5 (7)	N11—C11—C21—O2	−83.3 (8)
O3—N11—C11—C21	−70.0 (6)

Symmetry codes: (i) −y+1, x−y+1, z; (ii) −x+y, −x+1, z.