Acta Cryst.(2003). E59, m1151±m1153 DOI: 10.1107/S1600536803026242 Lee and Harrison (C7H10N)2[HAsO4]H2O
m1151
metal-organic papers
Acta Crystallographica Section E Structure Reports Online
ISSN 1600-5368
Bis(benzylammonium) hydrogenarsenate
monohydrate
Clare Lee and
William T. A. Harrison*
Department of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland
Correspondence e-mail: w.harrison@abdn.ac.uk
Key indicators Single-crystal X-ray study T= 120 K
Mean(C±C) = 0.006 AÊ Disorder in main residue Rfactor = 0.045 wRfactor = 0.112
Data-to-parameter ratio = 24.3
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2003 International Union of Crystallography Printed in Great Britain ± all rights reserved
The title compound, (C6H5CH2NH3)2[HAsO4]H2O, contains
a network of benzylammonium cations, hydrogenarsenate anions [dav(AsÐO) = 1.689 (2) AÊ] and water molecules. The
crystal packing involves NÐH O [dav(H O) = 1.91 AÊ,
av(NÐH O) = 167anddav(N O) = 2.794 (3) AÊ] and OÐ
H O [dav(H O) = 1.83 AÊ, av(OÐH O) = 173 and
dav(O O) = 2.729 (3) AÊ] hydrogen bonds, resulting in a
layered structure.
Comment
The title compound, (I) (Fig. 1), was prepared as part of our ongoing studies of hydrogen-bonding interactions in the crystal structures of (protonated) amine phosphates (Demiret al., 2003), phosphites (Harrison, 2003), selenites (Ritchie & Harrison, 2003) and arsenates (Lee & Harrison, 2003).
The crystal structure of (I) contains two unique C6H5CH2NH3+ benzylammonium cations, one unique
[HAsO4]2ÿ hydrogenarsenate anion and one unique water
molecule. The phenyl ring of the N2 benzylammonium species is disordered over two orientations twisted approximately about the C8ÐC9a/b C12a/baxis [dihedral angle between
the ring planes = 29.6; relative populations =
0.597 (7):0.403 (7) for the C9±C14 atoms with suf®xesaandb, respectively]. Otherwise, the geometrical parameters for the organic species are not signi®cantly different from those of the same cation in the non-linear optical material
benzyl-Received 4 November 2003 Accepted 13 November 2003 Online 22 November 2003
Figure 1
metal-organic papers
m1152
Lee and Harrison (C7H10N)2[HAsO4]H2O Acta Cryst.(2003). E59, m1151±m1153 ammonium dihydrogenphosphate, (C6H5CH2NH3)[H2PO4](Aakeroyet al., 1989).
The [HAsO4]2ÿ hydrogenarsenate group in (I) shows its
standard (Lee & Harrison, 2003) tetrahedral geometry [dav(AsÐO) = 1.689 (2) AÊ andav(OÐAsÐO) = 109.4 (1)],
with the protonated AsÐO4 vertex showing its expected lengthening relative to the other AsÐO bonds.
As well as electrostatic attractions, the component species in (I) interact by means of a network of NÐH O and OÐ H O links (Table 2). The [HAsO4]2ÿ units and the water
molecule (atom O5) are linked into a polymeric chain in the [010] direction by hydrogen bonds (Fig. 2). Inversion symmetry generates linked pairs of [HAsO4]2ÿunits (by way
of two O4ÐH1 O3 bonds) which, in turn, are bridged by pairs of water molecules. The hydrogen-bonding scheme in propane-1,2-diammonium hydrogenarsenate monohydrate (Lee & Harrison, 2003) led to a quite different arrangement of [HAsO4]2ÿ and H2O units. In 4-carboxyanilinium
di-hydrogenarsenate monohydrate (Tordjman et al., 1988), hydrogen bonding between the [H2AsO4]ÿand H2O species
results in a sheet structure, but otherwise structural data are lacking for these systems.
The organic species interact with the hydrogenarsenate/ water chains by way of NÐH OÐAs hydrogen bonds (Table 2). All six of the NH3+H atoms are involved in these
links [dav(H O) = 1.91 AÊ, av(NÐH O) = 167 and
dav(N O) = 2.794 (3) AÊ]. This results in (001)
hydrogen-arsenate/water/ammonium layers sandwiched between the benzyl moieties (Fig. 3) which, in turn, interact by way of van der Waals forces. A PLATON (Spek, 2003) analysis of (I) indicated that the minimum separation between phenyl ring centroids is 4.06 AÊ; therefore, any±stacking interactions in (I) are extremely weak.
Experimental
4 ml of a 1Mbenzylamine aqueous solution was added to 8 ml of a 0.5M H3AsO4 aqueous solution, resulting in a brown solution. A
mass of plate-shaped slightly translucent crystals of (I) grew as the water evaporated over the course of a few days.
Crystal data
(C7H10N)2[HAsO4]H2O
Mr= 374.26 Triclinic,P1
a= 6.4400 (2) AÊ
b= 8.9128 (3) AÊ
c= 14.9957 (5) AÊ
= 99.7048 (11)
= 93.1574 (12)
= 97.7776 (18)
V= 837.93 (5) AÊ3
Z= 2
Dx= 1.483 Mg mÿ3 MoKradiation
Cell parameters from 24 435 re¯ections
= 2.9±27.5
= 2.05 mmÿ1
T= 120 (2) K Plate, colourless 0.350.120.03 mm
Data collection
Enraf±Nonius KappaCCD diffractometer
!and'scans
Absorption correction: multi-scan (SORTAV; Blessing, 1995)
Tmin= 0.534,Tmax= 0.941 18 359 measured re¯ections
3846 independent re¯ections 3538 re¯ections withI> 2(I)
Rint= 0.122
max= 27.5
h=ÿ8!8
k=ÿ11!11
l=ÿ19!19
Re®nement
Re®nement onF2
R[F2> 2(F2)] = 0.045
wR(F2) = 0.112
S= 1.02 3846 re¯ections 158 parameters
H-atom parameters constrained
w= 1/[2(F
o2) + (0.0281P)2 + 2.1999P]
whereP= (Fo2+ 2Fc2)/3 (/)max= 0.001
max= 1.39 e AÊÿ3 min=ÿ0.69 e AÊÿ3
Extinction correction:SHELXL97 Extinction coef®cient: 0.021 (2)
Table 1
Selected geometric parameters (AÊ).
As1ÐO1 1.666 (2)
As1ÐO2 1.675 (2) As1ÐO3As1ÐO4 1.681 (2)1.732 (2)
Table 2
Hydrogen-bonding geometry (AÊ,).
DÐH A DÐH H A D A DÐH A
O4ÐH1 O3i 0.89 1.74 2.632 (3) 173 N1ÐH4 O2ii 0.91 1.94 2.830 (3) 166 N1ÐH5 O2iii 0.91 1.99 2.843 (3) 155 N1ÐH6 O1 0.91 1.80 2.704 (3) 174 N2ÐH7 O1iv 0.91 1.86 2.731 (3) 161 N2ÐH8 O5 0.91 1.92 2.823 (3) 174 N2ÐH9 O3 0.91 1.94 2.835 (3) 169 O5ÐH2 O3iii 0.96 1.78 2.731 (3) 171 O5ÐH3 O2ii 0.85 1.98 2.825 (2) 176
Symmetry codes: (i) 2ÿx;1ÿy;1ÿz; (ii) 1ÿx;ÿy;1ÿz; (iii) xÿ1;y;z; (iv) 1ÿx;1ÿy;1ÿz.
Figure 2
Detail of a hydrogen-bonded hydrogenarsenate/water chain in (I). Colour key: [HAsO4]2ÿtetrahedra green, O atoms rose and H atoms
grey. The H O portions of the hydrogen bonds are highlighted in yellow. Symmetry labels as in Table 2; additionally, (v) 1 +x, y, z; (vi) 1 +x, 1 +y, z.
Figure 3
The C atoms forming the two orientations of the disordered phenyl group (atoms C9a±C14aand C9b±C14b) were constrained to lie at the vertices of regular hexagons, with d(CÐC) = 1.39 AÊ, and were re®ned isotropically. The OÐH H atoms were found in difference maps and re®ned as riding, starting from these positions. The H atoms bonded to C and N atoms were placed in calculated positions [d(CÐH) = 0.95±0.99 AÊ andd(NÐH) = 0.91 AÊ] and re®ned as riding, allowing free rotation of the rigid RÐNH3 groups
about the RÐN bonds. The constraint Uiso(H) = 1.2Ueq(parent
atom) was applied in all cases. The highest difference peak is 0.54 AÊ from C12band the deepest difference hole is 0.79 AÊ from As1.
Data collection:COLLECT(Nonius, 1999); cell re®nement:HKL SCALEPACK(Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK, and SORTAV (Blessing, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to re®ne structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) andATOMS(Shape Software, 1999); software used to prepare material for publication:SHELXL97.
We thank the EPSRC UK National Crystallography Service (University of Southampton) for data collection.
References
Aakeroy, C. B., Hitchcock, P. B., Moyle, B. D., Seddon, K. R. (1989).J. Chem. Soc. Chem. Commun.pp. 1856±1859.
Blessing, R. H. (1995).Acta Cryst.A51, 33±38.
Demir, S., Yilmaz, V. T. & Harrison, W. T. A. (2003).Acta Cryst.E59, o907± o909.
Enraf±Nonius (1999).COLLECT. Nonius BV, Delft, The Netherlands. Farrugia, L. J. (1997).J. Appl. Cryst.30, 565.
Harrison, W. T. A. (2003).Acta Cryst.E59, o1267±o1269. Lee, C. & Harrison, W. T. A. (2003).Acta Cryst.E59, m739±m741. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307±326. New York: Academic Press.
Ritchie, L. K. & Harrison, W. T. A. (2003).Acta Cryst.E59, o1296±o1298. Shape Software (1999).ATOMS. Shape Software, 525 Hidden Valley Road,
Kingsport, Tennessee, USA.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of GoÈttingen, Germany.
Spek, A. L. (2003).J. Appl. Cryst.36, 7±13.
Tordjman, I., Masse, R. & Guitel, J. C. (1988).Acta Cryst.C44, 2057±2059.
supporting information
sup-1 Acta Cryst. (2003). E59, m1151–m1153
supporting information
Acta Cryst. (2003). E59, m1151–m1153 [https://doi.org/10.1107/S1600536803026242]
Bis(benzylammonium) hydrogenarsenate monohydrate
Clare Lee and William T. A. Harrison
(I)
Crystal data
(C7H10N)2[HAsO4]·H2O Mr = 374.26
Triclinic, P1 Hall symbol: -P 1 a = 6.4400 (2) Å b = 8.9128 (3) Å c = 14.9957 (5) Å α = 99.7048 (11)° β = 93.1574 (12)° γ = 97.7776 (18)° V = 837.93 (5) Å3
Z = 2 F(000) = 388 Dx = 1.483 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 24435 reflections θ = 2.9–27.5°
µ = 2.05 mm−1 T = 120 K Plate, colourless 0.35 × 0.12 × 0.03 mm
Data collection
Enraf-Nonius KappaCCD diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
ω and φ scans
Absorption correction: multi-scan (SORTAV; Blessing, 1995) Tmin = 0.534, Tmax = 0.941
18359 measured reflections 3846 independent reflections 3538 reflections with I > 2σ(I) Rint = 0.122
θmax = 27.5°, θmin = 2.9° h = −8→8
k = −11→11 l = −19→19
Refinement
Refinement on F2
Least-squares matrix: full R[F2 > 2σ(F2)] = 0.045 wR(F2) = 0.112 S = 1.02 3846 reflections 158 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained w = 1/[σ2(F
o2) + (0.0281P)2 + 2.1999P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 1.39 e Å−3
Δρmin = −0.69 e Å−3
Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
supporting information
sup-2 Acta Cryst. (2003). E59, m1151–m1153
Special details
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)
x y z Uiso*/Ueq Occ. (<1)
As1 0.79069 (5) 0.27362 (3) 0.455577 (19) 0.01615 (13) O1 0.5423 (3) 0.3057 (2) 0.44548 (14) 0.0206 (4) O2 0.8133 (3) 0.0866 (2) 0.43007 (14) 0.0199 (4) O3 0.9006 (3) 0.3503 (2) 0.56046 (14) 0.0198 (4) O4 0.9323 (4) 0.3618 (3) 0.37887 (14) 0.0242 (5)
H1 0.9963 0.4563 0.4027 0.029*
N1 0.2439 (4) 0.0543 (3) 0.41567 (17) 0.0191 (5)
H4 0.2482 0.0079 0.4652 0.023*
H5 0.1122 0.0767 0.4048 0.023*
H6 0.3375 0.1428 0.4261 0.023*
C1 0.3001 (5) −0.0517 (4) 0.3348 (2) 0.0219 (6)
H10 0.2091 −0.1524 0.3282 0.026*
H11 0.4477 −0.0687 0.3447 0.026*
C2 0.2742 (5) 0.0126 (3) 0.2489 (2) 0.0225 (6)
C3 0.4443 (7) 0.0443 (5) 0.1989 (3) 0.0355 (8)
H12 0.5806 0.0292 0.2198 0.043*
C4 0.4147 (8) 0.0988 (5) 0.1177 (3) 0.0438 (10)
H13 0.5314 0.1191 0.0832 0.053*
C5 0.2200 (8) 0.1232 (5) 0.0871 (2) 0.0421 (10)
H14 0.2015 0.1603 0.0319 0.050*
C6 0.0526 (8) 0.0937 (6) 0.1370 (3) 0.0593 (15)
H15 −0.0827 0.1114 0.1164 0.071*
C7 0.0783 (7) 0.0382 (6) 0.2174 (3) 0.0470 (11)
H16 −0.0397 0.0175 0.2511 0.056*
N2 0.5536 (4) 0.4647 (3) 0.64221 (17) 0.0208 (5)
H7 0.5098 0.5232 0.6027 0.025*
H8 0.4500 0.3855 0.6446 0.025*
H9 0.6708 0.4266 0.6232 0.025*
C8 0.6026 (2) 0.56092 (16) 0.73401 (9) 0.0285 (7)
H17 0.4768 0.6071 0.7527 0.034*
H18 0.7167 0.6460 0.7312 0.034*
C9A 0.6777 (2) 0.47374 (16) 0.80588 (9) 0.023 (3)* 0.50
C10A 0.8731 (2) 0.42391 (16) 0.80400 (9) 0.0350 (15)* 0.596 (7)
H10A 0.9619 0.4441 0.7575 0.042* 0.596 (7)
supporting information
sup-3 Acta Cryst. (2003). E59, m1151–m1153
H11A 1.0722 0.3104 0.8688 0.051* 0.596 (7)
C12A 0.8088 (2) 0.31491 (16) 0.93803 (9) 0.049 (2)* 0.596 (7)
H12A 0.8536 0.2606 0.9832 0.059* 0.596 (7)
C13A 0.6134 (2) 0.36474 (16) 0.93991 (9) 0.0471 (19)* 0.596 (7)
H13A 0.5247 0.3445 0.9864 0.057* 0.596 (7)
C14A 0.5479 (2) 0.44416 (16) 0.87384 (9) 0.0403 (17)* 0.596 (7)
H14A 0.4144 0.4782 0.8751 0.048* 0.596 (7)
C9B 0.6550 (2) 0.46838 (16) 0.80328 (9) 0.028 (3)* 0.50
C10B 0.8649 (2) 0.47486 (16) 0.83297 (9) 0.034 (2)* 0.404 (7)
H10B 0.9716 0.5340 0.8070 0.041* 0.404 (7)
C11B 0.9186 (2) 0.39476 (16) 0.90066 (9) 0.033 (2)* 0.404 (7)
H11B 1.0621 0.3992 0.9210 0.040* 0.404 (7)
C12B 0.7625 (2) 0.30818 (16) 0.93865 (9) 0.027 (2)* 0.404 (7)
H12B 0.7993 0.2534 0.9849 0.033* 0.404 (7)
C13B 0.5527 (2) 0.30170 (16) 0.90895 (9) 0.030 (2)* 0.404 (7)
H13B 0.4460 0.2425 0.9349 0.036* 0.404 (7)
C14B 0.4989 (2) 0.38179 (16) 0.84127 (9) 0.0250 (19)* 0.404 (7)
H14B 0.3555 0.3774 0.8210 0.030* 0.404 (7)
O5 0.2125 (2) 0.22976 (16) 0.64252 (9) 0.0247 (5)
H2 0.0966 0.2619 0.6114 0.030*
H3 0.2019 0.1337 0.6227 0.030*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
As1 0.02293 (19) 0.00932 (18) 0.01604 (18) 0.00171 (11) 0.00122 (11) 0.00244 (11) O1 0.0236 (11) 0.0138 (10) 0.0238 (11) 0.0024 (8) −0.0011 (9) 0.0032 (8) O2 0.0276 (11) 0.0085 (9) 0.0233 (11) 0.0041 (8) 0.0021 (9) 0.0007 (8) O3 0.0272 (11) 0.0123 (10) 0.0182 (10) −0.0002 (8) −0.0023 (8) 0.0012 (8) O4 0.0338 (13) 0.0158 (10) 0.0201 (11) −0.0056 (9) 0.0068 (9) 0.0006 (8) N1 0.0233 (13) 0.0141 (12) 0.0201 (12) 0.0010 (10) 0.0003 (10) 0.0057 (10) C1 0.0302 (16) 0.0152 (14) 0.0207 (15) 0.0041 (12) 0.0037 (12) 0.0034 (11) C2 0.0322 (17) 0.0156 (14) 0.0175 (14) −0.0014 (12) 0.0008 (12) 0.0012 (11) C3 0.047 (2) 0.035 (2) 0.0308 (18) 0.0178 (17) 0.0169 (16) 0.0113 (15) C4 0.069 (3) 0.038 (2) 0.032 (2) 0.016 (2) 0.026 (2) 0.0133 (17) C5 0.071 (3) 0.030 (2) 0.0209 (17) −0.0076 (19) −0.0081 (18) 0.0076 (14) C6 0.048 (3) 0.077 (4) 0.054 (3) −0.019 (2) −0.024 (2) 0.044 (3) C7 0.032 (2) 0.066 (3) 0.045 (2) −0.0119 (19) −0.0092 (17) 0.037 (2) N2 0.0300 (14) 0.0135 (12) 0.0196 (12) 0.0052 (10) 0.0020 (10) 0.0031 (10) C8 0.051 (2) 0.0137 (15) 0.0203 (15) 0.0066 (14) 0.0046 (14) −0.0011 (12) O5 0.0300 (12) 0.0138 (10) 0.0292 (12) 0.0031 (9) −0.0025 (9) 0.0022 (9)
Geometric parameters (Å, º)
As1—O1 1.666 (2) C8—C9A 1.5252
As1—O2 1.675 (2) C8—H17 0.9900
As1—O3 1.681 (2) C8—H18 0.9900
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sup-4 Acta Cryst. (2003). E59, m1151–m1153
O4—H1 0.8919 C9A—C14A 1.3900
N1—C1 1.499 (4) C10A—C11A 1.3900
N1—H4 0.9100 C10A—H10A 0.9500
N1—H5 0.9100 C11A—C12A 1.3900
N1—H6 0.9100 C11A—H11A 0.9500
C1—C2 1.506 (4) C12A—C13A 1.3900
C1—H10 0.9900 C12A—H12A 0.9500
C1—H11 0.9900 C13A—C14A 1.3900
C2—C7 1.384 (5) C13A—H13A 0.9500
C2—C3 1.385 (5) C14A—H14A 0.9500
C3—C4 1.398 (6) C9B—C10B 1.3900
C3—H12 0.9500 C9B—C14B 1.3900
C4—C5 1.369 (6) C10B—C11B 1.3900
C4—H13 0.9500 C10B—H10B 0.9500
C5—C6 1.367 (7) C11B—C12B 1.3900
C5—H14 0.9500 C11B—H11B 0.9500
C6—C7 1.389 (6) C12B—C13B 1.3900
C6—H15 0.9500 C12B—H12B 0.9500
C7—H16 0.9500 C13B—C14B 1.3900
N2—C8 1.487 (3) C13B—H13B 0.9500
N2—H7 0.9100 C14B—H14B 0.9500
N2—H8 0.9100 O5—H2 0.9595
N2—H9 0.9100 O5—H3 0.8499
C8—C9B 1.4829
O1—As1—O2 112.66 (11) N2—C8—C9A 113.84 (11)
O1—As1—O3 110.23 (11) C9B—C8—H17 106.8
O2—As1—O3 110.89 (10) N2—C8—H17 109.0
O1—As1—O4 109.09 (11) C9A—C8—H17 110.1
O2—As1—O4 105.84 (10) C9B—C8—H18 112.1
O3—As1—O4 107.92 (11) N2—C8—H18 109.1
As1—O4—H1 113.0 C9A—C8—H18 106.8
C1—N1—H4 109.5 H17—C8—H18 107.8
C1—N1—H5 109.5 C10A—C9A—C14A 120.0
H4—N1—H5 109.5 C10A—C9A—C8 120.9
C1—N1—H6 109.5 C14A—C9A—C8 119.1
H4—N1—H6 109.5 C11A—C10A—C9A 120.0
H5—N1—H6 109.5 C11A—C10A—H10A 120.0
N1—C1—C2 111.8 (2) C9A—C10A—H10A 120.0
N1—C1—H10 109.3 C10A—C11A—C12A 120.0
C2—C1—H10 109.3 C10A—C11A—H11A 120.0
N1—C1—H11 109.3 C12A—C11A—H11A 120.0
C2—C1—H11 109.3 C13A—C12A—C11A 120.0
H10—C1—H11 107.9 C13A—C12A—H12A 120.0
C7—C2—C3 118.8 (3) C11A—C12A—H12A 120.0
C7—C2—C1 120.4 (3) C14A—C13A—C12A 120.0
C3—C2—C1 120.9 (3) C14A—C13A—H13A 120.0
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sup-5 Acta Cryst. (2003). E59, m1151–m1153
C2—C3—H12 120.1 C13A—C14A—C9A 120.0
C4—C3—H12 120.1 C13A—C14A—H14A 120.0
C5—C4—C3 120.9 (4) C9A—C14A—H14A 120.0
C5—C4—H13 119.5 C10B—C9B—C14B 120.0
C3—C4—H13 119.5 C10B—C9B—C8 118.6
C6—C5—C4 119.3 (4) C14B—C9B—C8 121.4
C6—C5—H14 120.3 C9B—C10B—C11B 120.0
C4—C5—H14 120.3 C9B—C10B—H10B 120.0
C5—C6—C7 120.6 (4) C11B—C10B—H10B 120.0
C5—C6—H15 119.7 C12B—C11B—C10B 120.0
C7—C6—H15 119.7 C12B—C11B—H11B 120.0
C2—C7—C6 120.6 (4) C10B—C11B—H11B 120.0
C2—C7—H16 119.7 C13B—C12B—C11B 120.0
C6—C7—H16 119.7 C13B—C12B—H12B 120.0
C8—N2—H7 109.5 C11B—C12B—H12B 120.0
C8—N2—H8 109.5 C12B—C13B—C14B 120.0
H7—N2—H8 109.5 C12B—C13B—H13B 120.0
C8—N2—H9 109.5 C14B—C13B—H13B 120.0
H7—N2—H9 109.5 C13B—C14B—C9B 120.0
H8—N2—H9 109.5 C13B—C14B—H14B 120.0
C9B—C8—N2 111.92 (11) C9B—C14B—H14B 120.0
C9B—C8—C9A 5.4 H2—O5—H3 104.7
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
O4—H1···O3i 0.89 1.74 2.632 (3) 173
N1—H4···O2ii 0.91 1.94 2.830 (3) 166
N1—H5···O2iii 0.91 1.99 2.843 (3) 155
N1—H6···O1 0.91 1.80 2.704 (3) 174
N2—H7···O1iv 0.91 1.86 2.731 (3) 161
N2—H8···O5 0.91 1.92 2.823 (3) 174
N2—H9···O3 0.91 1.94 2.835 (3) 169
O5—H2···O3iii 0.96 1.78 2.731 (3) 171
O5—H3···O2ii 0.85 1.98 2.825 (2) 176
