Benzamidinium tetra-hydro-penta-borate sesquihydrate.

THE ASYMMETRIC UNIT OF THE TITLE COMPOUND [SYSTEMATIC NAME: benzamidinium 3,3',5,5'-tetra-hydr-oxy-1,1'-spirobi[2,4,6-trioxa-1,3,5-triboracyclo-hexa-ne](1-) sesquihydrate], C(7)H(9)N(2) (+)·B(5)H(4)O(10) (-)·1.5H(2)O, is composed of two protonated benzamidinium cations, two tetra-hydro-penta-borate anions and three water mol-ecules of crystallization. The ions and water molecules are associated in the crystal structure by an extensive three-dimensional hydrogen-bonding network, which consists mainly of cation-to-anion N-H⋯O and anion-to-anion O-H⋯O hydrogen bonds.

Related literature

For crystal structure determinations of the tetra­hydro­penta­borate anion, see: Loboda et al., (1993 ▶, 1994 ▶); Wiebcke et al. (1993 ▶); Turdybekov et al. (1992 ▶); Freyhardt et al. (1994 ▶); Baber et al. (2004 ▶). For the computation of ring patterns formed by hydrogen bonds in crystal structures, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶); Motherwell et al. (1999 ▶). For hydration in mol­ecular crystals, see: Gillon et al. (2003 ▶).

Experimental

Crystal data

C7H9N2 +·B5H4O10 −·1.5H2O

M = 366.27

Triclinic,

a = 8.22314 (19) Å

b = 10.7814 (2) Å

c = 19.1997 (3) Å

α = 75.9475 (11)°

β = 85.4458 (16)°

γ = 73.6979 (13)°

V = 1584.74 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 298 (2) K

0.15 × 0.12 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur S CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.975, T max = 0.988

142668 measured reflections

9063 independent reflections

5688 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.098

S = 0.99

9063 reflections

542 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction 2006 ▶); cell refinement: CrysAlis RED(Oxford Diffraction 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017522/rz2220sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017522/rz2220Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C7H9N2+·B5H4O10–·1.5H2O	Z = 4
Mr = 366.27	F000 = 756
Triclinic, P1	Dx = 1.535 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.22314 (19) Å	Cell parameters from 36413 reflections
b = 10.7814 (2) Å	θ = 2.6–32.6º
c = 19.1997 (3) Å	µ = 0.14 mm−1
α = 75.9475 (11)º	T = 298 (2) K
β = 85.4458 (16)º	Block, colourless
γ = 73.6979 (13)º	0.15 × 0.12 × 0.10 mm
V = 1584.74 (5) Å3

Oxford Diffraction Xcalibur S CCD diffractometer	9063 independent reflections
Radiation source: Enhance (Mo) X-ray source	5688 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.050
Detector resolution: 16.0696 pixels mm-1	θmax = 30.0º
T = 298(2) K	θmin = 2.6º
ω and φ scans	h = −11→11
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2006)	k = −15→15
Tmin = 0.975, Tmax = 0.988	l = −27→27
142668 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0514P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.001
9063 reflections	Δρmax = 0.23 e Å−3
542 parameters	Δρmin = −0.22 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
B1	0.15368 (18)	0.67509 (13)	0.78017 (7)	0.0240 (3)
O1	0.18508 (11)	0.67022 (8)	0.85446 (4)	0.0285 (2)
B2	0.10340 (19)	0.61230 (14)	0.91179 (7)	0.0264 (3)
O2	0.13937 (14)	0.61947 (10)	0.97783 (5)	0.0411 (3)
H2	0.088 (2)	0.5797 (18)	1.0104 (10)	0.061 (5)*
O3	−0.01246 (12)	0.54462 (9)	0.90282 (4)	0.0324 (2)
O4	−0.14621 (13)	0.46036 (10)	0.82903 (6)	0.0414 (3)
H4	−0.146 (2)	0.4444 (19)	0.7868 (11)	0.065 (6)*
B3	−0.03994 (19)	0.53439 (14)	0.83403 (7)	0.0275 (3)
O5	0.03619 (11)	0.59533 (9)	0.77633 (4)	0.0298 (2)
O6	0.31411 (11)	0.61782 (8)	0.74602 (4)	0.0276 (2)
O7	0.49090 (14)	0.60254 (10)	0.64314 (5)	0.0415 (3)
H7	0.536 (3)	0.521 (2)	0.6692 (12)	0.082 (7)*
O8	0.25892 (12)	0.78921 (9)	0.63891 (4)	0.0337 (2)
B4	0.3560 (2)	0.66751 (14)	0.67700 (7)	0.0282 (3)
O9	0.05933 (13)	0.99063 (9)	0.63637 (5)	0.0370 (2)
H9	−0.009 (3)	1.037 (2)	0.6630 (11)	0.071 (6)*
O10	0.08133 (11)	0.81424 (8)	0.74163 (4)	0.0286 (2)
B5	0.13056 (19)	0.86493 (14)	0.67397 (7)	0.0261 (3)
B1A	0.20283 (19)	0.70679 (14)	0.31266 (7)	0.0251 (3)
O1A	0.14676 (11)	0.85043 (8)	0.27918 (4)	0.0294 (2)
B2A	0.22073 (19)	0.90684 (14)	0.21888 (7)	0.0256 (3)
O2A	0.16712 (13)	1.03877 (9)	0.18762 (5)	0.0331 (2)
H2A	0.088 (2)	1.0818 (18)	0.2128 (10)	0.058 (6)*
O3A	0.35330 (12)	0.83347 (9)	0.18527 (5)	0.0347 (2)
O4A	0.55788 (14)	0.63416 (10)	0.18374 (5)	0.0400 (3)
H4A	0.602 (3)	0.551 (2)	0.2064 (11)	0.077 (6)*
B3A	0.4266 (2)	0.70280 (14)	0.21817 (7)	0.0277 (3)
O5A	0.36698 (11)	0.64584 (8)	0.28257 (4)	0.0304 (2)
O6A	0.08059 (12)	0.63966 (9)	0.29702 (5)	0.0338 (2)
O7A	−0.14440 (18)	0.53852 (17)	0.33468 (7)	0.0770 (5)
H7A	−0.126 (3)	0.513 (2)	0.2918 (12)	0.094 (7)*
O8A	−0.04403 (13)	0.63084 (11)	0.41341 (5)	0.0448 (3)
B4A	−0.0342 (2)	0.60380 (18)	0.34663 (9)	0.0398 (4)
O9A	0.09860 (16)	0.66666 (12)	0.50576 (5)	0.0491 (3)
H9A	0.018 (3)	0.641 (2)	0.5317 (11)	0.075 (6)*
O10A	0.21717 (11)	0.69028 (9)	0.38973 (4)	0.0302 (2)
B5A	0.0913 (2)	0.66232 (15)	0.43589 (8)	0.0318 (3)
N1	0.67173 (18)	0.80236 (14)	−0.07944 (6)	0.0402 (3)
H11	0.631 (2)	0.7525 (17)	−0.0989 (9)	0.051 (5)*
H12	0.716 (2)	0.8610 (17)	−0.1079 (9)	0.050 (5)*
N2	0.61716 (17)	0.68505 (12)	0.03102 (7)	0.0385 (3)
H21	0.581 (2)	0.6316 (16)	0.0105 (9)	0.048 (5)*
H22	0.599 (2)	0.6779 (16)	0.0763 (10)	0.049 (5)*
C1	0.73291 (16)	0.87110 (13)	0.02400 (7)	0.0301 (3)
C2	0.71988 (18)	1.00220 (14)	−0.01273 (8)	0.0370 (3)
H2B	0.6713	1.0354	−0.0603	0.044*
C3	0.7765 (2)	1.08450 (15)	0.01889 (9)	0.0471 (4)
H3	0.7675	1.1756	−0.0066	0.057*
C4	0.8452 (2)	1.03783 (17)	0.08617 (10)	0.0528 (4)
H4B	0.8834	1.0965	0.1083	0.063*
C5	0.8603 (2)	0.90783 (18)	0.12271 (9)	0.0514 (4)
H5	0.9105	0.8751	0.1700	0.062*
C6	0.80389 (19)	0.82453 (15)	0.09177 (8)	0.0412 (3)
H6	0.8139	0.7334	0.1175	0.049*
C7	0.67193 (16)	0.78329 (13)	−0.00935 (7)	0.0297 (3)
N1A	0.3078 (2)	0.85153 (14)	0.48086 (8)	0.0550 (4)
H11A	0.325 (2)	0.8023 (18)	0.4498 (10)	0.058 (5)*
H12A	0.268 (2)	0.8266 (18)	0.5252 (11)	0.061 (5)*
N2A	0.2464 (2)	1.06351 (15)	0.49387 (7)	0.0478 (4)
H21A	0.254 (2)	1.1441 (19)	0.4800 (10)	0.063 (6)*
H22A	0.193 (2)	1.0430 (17)	0.5356 (10)	0.058 (5)*
C1A	0.38252 (19)	1.01425 (14)	0.38368 (7)	0.0358 (3)
C2A	0.5160 (2)	0.92500 (17)	0.35919 (8)	0.0490 (4)
H23A	0.5592	0.8364	0.3889	0.059*
C3A	0.5890 (2)	0.96110 (19)	0.29228 (9)	0.0571 (5)
H3A	0.6822	0.8976	0.2750	0.069*
C4A	0.5286 (2)	1.08720 (19)	0.25051 (8)	0.0550 (5)
H41A	0.5811	1.1131	0.2042	0.066*
C5A	0.3948 (2)	1.17638 (17)	0.27401 (8)	0.0493 (4)
H5A	0.3524	1.2648	0.2441	0.059*
C6A	0.3197 (2)	1.14088 (15)	0.34044 (7)	0.0411 (3)
H6A	0.2240	1.2038	0.3567	0.049*
C7A	0.30793 (19)	0.97547 (15)	0.45592 (7)	0.0378 (3)
O1W	0.53676 (17)	0.59539 (14)	−0.10037 (7)	0.0554 (3)
H11W	0.441 (3)	0.614 (2)	−0.1163 (13)	0.089*
H12W	0.603 (3)	0.545 (2)	−0.1244 (12)	0.089*
O2W	−0.25372 (16)	0.66371 (12)	0.54656 (6)	0.0512 (3)
H21W	−0.296 (3)	0.649 (2)	0.5068 (12)	0.082*
H22W	−0.335 (3)	0.651 (2)	0.5809 (12)	0.082*
O3W	−0.41457 (19)	0.58780 (16)	0.44572 (9)	0.0732 (4)
H31W	−0.492 (4)	0.568 (2)	0.4515 (8)	0.117*
H32W	−0.329 (3)	0.549 (3)	0.4128 (15)	0.117*

	U11	U22	U33	U12	U13	U23
B1	0.0284 (8)	0.0219 (7)	0.0200 (6)	−0.0071 (6)	0.0052 (6)	−0.0030 (5)
O1	0.0352 (5)	0.0315 (5)	0.0218 (4)	−0.0160 (4)	0.0038 (4)	−0.0049 (4)
B2	0.0314 (8)	0.0229 (7)	0.0236 (6)	−0.0070 (6)	0.0053 (6)	−0.0052 (5)
O2	0.0598 (7)	0.0498 (6)	0.0233 (5)	−0.0322 (6)	0.0054 (5)	−0.0078 (4)
O3	0.0402 (5)	0.0402 (5)	0.0224 (4)	−0.0222 (5)	0.0081 (4)	−0.0070 (4)
O4	0.0500 (6)	0.0522 (6)	0.0330 (5)	−0.0315 (5)	0.0091 (5)	−0.0129 (5)
B3	0.0278 (8)	0.0276 (7)	0.0271 (7)	−0.0081 (7)	0.0052 (6)	−0.0071 (6)
O5	0.0369 (5)	0.0338 (5)	0.0222 (4)	−0.0170 (4)	0.0050 (4)	−0.0061 (4)
O6	0.0298 (5)	0.0230 (4)	0.0245 (4)	−0.0036 (4)	0.0067 (4)	−0.0013 (3)
O7	0.0450 (6)	0.0287 (5)	0.0366 (5)	0.0006 (5)	0.0203 (5)	−0.0003 (4)
O8	0.0427 (6)	0.0266 (5)	0.0232 (4)	−0.0019 (4)	0.0090 (4)	−0.0016 (4)
B4	0.0306 (8)	0.0252 (7)	0.0262 (7)	−0.0073 (7)	0.0062 (6)	−0.0038 (6)
O9	0.0433 (6)	0.0262 (5)	0.0293 (5)	0.0011 (5)	0.0089 (4)	0.0009 (4)
O10	0.0313 (5)	0.0230 (4)	0.0251 (4)	−0.0024 (4)	0.0077 (4)	−0.0021 (3)
B5	0.0283 (8)	0.0250 (7)	0.0234 (6)	−0.0065 (7)	0.0033 (6)	−0.0046 (6)
B1A	0.0308 (8)	0.0224 (7)	0.0213 (6)	−0.0086 (6)	0.0070 (6)	−0.0041 (5)
O1A	0.0314 (5)	0.0227 (4)	0.0290 (4)	−0.0046 (4)	0.0097 (4)	−0.0025 (3)
B2A	0.0287 (8)	0.0234 (7)	0.0225 (6)	−0.0061 (7)	0.0020 (6)	−0.0030 (5)
O2A	0.0392 (6)	0.0231 (5)	0.0298 (5)	−0.0035 (5)	0.0113 (4)	−0.0022 (4)
O3A	0.0403 (6)	0.0254 (5)	0.0273 (4)	−0.0006 (4)	0.0132 (4)	0.0008 (4)
O4A	0.0451 (6)	0.0278 (5)	0.0310 (5)	0.0040 (5)	0.0176 (5)	0.0016 (4)
B3A	0.0313 (8)	0.0247 (7)	0.0243 (6)	−0.0062 (7)	0.0064 (6)	−0.0041 (6)
O5A	0.0340 (5)	0.0222 (4)	0.0273 (4)	−0.0031 (4)	0.0108 (4)	−0.0004 (3)
O6A	0.0428 (6)	0.0401 (5)	0.0258 (4)	−0.0227 (5)	0.0096 (4)	−0.0107 (4)
O7A	0.0885 (10)	0.1351 (13)	0.0538 (7)	−0.0873 (10)	0.0356 (7)	−0.0531 (8)
O8A	0.0456 (6)	0.0691 (7)	0.0348 (5)	−0.0343 (6)	0.0169 (5)	−0.0235 (5)
B4A	0.0435 (10)	0.0510 (10)	0.0350 (8)	−0.0250 (8)	0.0115 (7)	−0.0181 (7)
O9A	0.0629 (7)	0.0669 (7)	0.0265 (5)	−0.0346 (6)	0.0105 (5)	−0.0115 (5)
O10A	0.0352 (5)	0.0343 (5)	0.0226 (4)	−0.0143 (4)	0.0043 (4)	−0.0054 (4)
B5A	0.0396 (9)	0.0303 (8)	0.0263 (7)	−0.0122 (7)	0.0066 (6)	−0.0066 (6)
N1	0.0556 (8)	0.0442 (7)	0.0269 (6)	−0.0247 (7)	0.0057 (6)	−0.0083 (5)
N2	0.0525 (8)	0.0360 (7)	0.0302 (6)	−0.0198 (6)	0.0052 (6)	−0.0062 (5)
C1	0.0297 (7)	0.0317 (7)	0.0289 (6)	−0.0092 (6)	0.0054 (5)	−0.0079 (5)
C2	0.0374 (8)	0.0330 (7)	0.0385 (7)	−0.0088 (6)	0.0037 (6)	−0.0065 (6)
C3	0.0453 (9)	0.0326 (8)	0.0653 (11)	−0.0120 (7)	0.0026 (8)	−0.0141 (7)
C4	0.0461 (10)	0.0553 (10)	0.0698 (11)	−0.0189 (8)	0.0000 (8)	−0.0323 (9)
C5	0.0511 (10)	0.0648 (11)	0.0447 (9)	−0.0196 (9)	−0.0080 (7)	−0.0175 (8)
C6	0.0459 (9)	0.0409 (8)	0.0370 (7)	−0.0136 (7)	−0.0034 (6)	−0.0062 (6)
C7	0.0295 (7)	0.0286 (7)	0.0286 (6)	−0.0062 (6)	0.0039 (5)	−0.0055 (5)
N1A	0.0941 (12)	0.0436 (8)	0.0342 (7)	−0.0350 (8)	0.0173 (8)	−0.0086 (6)
N2A	0.0679 (10)	0.0420 (8)	0.0358 (7)	−0.0226 (7)	0.0164 (7)	−0.0096 (6)
C1A	0.0457 (9)	0.0414 (8)	0.0259 (6)	−0.0220 (8)	0.0011 (6)	−0.0067 (6)
C2A	0.0588 (11)	0.0464 (9)	0.0380 (8)	−0.0137 (9)	0.0055 (8)	−0.0050 (7)
C3A	0.0572 (11)	0.0706 (12)	0.0416 (9)	−0.0162 (10)	0.0106 (8)	−0.0142 (8)
C4A	0.0590 (11)	0.0799 (13)	0.0296 (7)	−0.0331 (11)	0.0037 (7)	−0.0037 (8)
C5A	0.0600 (11)	0.0554 (10)	0.0319 (7)	−0.0250 (9)	−0.0059 (7)	0.0039 (7)
C6A	0.0472 (9)	0.0451 (8)	0.0332 (7)	−0.0181 (7)	−0.0022 (6)	−0.0058 (6)
C7A	0.0462 (9)	0.0422 (8)	0.0293 (7)	−0.0219 (7)	0.0014 (6)	−0.0055 (6)
O1W	0.0458 (7)	0.0704 (9)	0.0604 (8)	−0.0210 (7)	−0.0036 (6)	−0.0271 (6)
O2W	0.0620 (8)	0.0562 (7)	0.0451 (6)	−0.0315 (6)	0.0243 (6)	−0.0193 (5)
O3W	0.0637 (10)	0.0796 (10)	0.0819 (10)	−0.0187 (8)	0.0071 (8)	−0.0325 (8)

B1—O1	1.4555 (15)	N1—H11	0.870 (18)
B1—O6	1.4674 (17)	N1—H12	0.872 (18)
B1—O10	1.4771 (15)	N2—C7	1.3188 (16)
B1—O5	1.4788 (16)	N2—H21	0.893 (17)
O1—B2	1.3553 (15)	N2—H22	0.858 (17)
B2—O2	1.3494 (16)	C1—C6	1.3874 (19)
B2—O3	1.3955 (16)	C1—C2	1.3962 (18)
O2—H2	0.83 (2)	C1—C7	1.4729 (18)
O3—B3	1.3929 (16)	C2—C3	1.382 (2)
O4—B3	1.3608 (17)	C2—H2B	0.9700
O4—H4	0.87 (2)	C3—C4	1.372 (2)
B3—O5	1.3484 (16)	C3—H3	0.9700
O6—B4	1.3593 (16)	C4—C5	1.382 (2)
O7—B4	1.3472 (19)	C4—H4B	0.9700
O7—H7	0.89 (2)	C5—C6	1.383 (2)
O8—B5	1.3798 (18)	C5—H5	0.9700
O8—B4	1.3900 (17)	C6—H6	0.9700
O9—B5	1.3592 (17)	N1A—C7A	1.3057 (19)
O9—H9	0.87 (2)	N1A—H11A	0.869 (19)
O10—B5	1.3588 (15)	N1A—H12A	0.892 (19)
B1A—O10A	1.4572 (15)	N2A—C7A	1.302 (2)
B1A—O5A	1.4664 (18)	N2A—H21A	0.86 (2)
B1A—O6A	1.4785 (16)	N2A—H22A	0.891 (19)
B1A—O1A	1.4788 (16)	C1A—C2A	1.377 (2)
O1A—B2A	1.3544 (16)	C1A—C6A	1.394 (2)
B2A—O2A	1.3613 (16)	C1A—C7A	1.4839 (18)
B2A—O3A	1.3721 (18)	C2A—C3A	1.389 (2)
O2A—H2A	0.87 (2)	C2A—H23A	0.9700
O3A—B3A	1.3778 (17)	C3A—C4A	1.376 (3)
O4A—B3A	1.3514 (19)	C3A—H3A	0.9700
O4A—H4A	0.89 (2)	C4A—C5A	1.370 (3)
B3A—O5A	1.3601 (16)	C4A—H41A	0.9700
O6A—B4A	1.3533 (18)	C5A—C6A	1.388 (2)
O7A—B4A	1.3559 (19)	C5A—H5A	0.9700
O7A—H7A	0.92 (2)	C6A—H6A	0.9700
O8A—B4A	1.3737 (18)	O1W—H11W	0.82 (2)
O8A—B5A	1.3781 (18)	O1W—H12W	0.85 (2)
O9A—B5A	1.3604 (18)	O2W—H21W	0.93 (2)
O9A—H9A	0.87 (2)	O2W—H22W	0.91 (2)
O10A—B5A	1.3592 (17)	O3W—H31W	0.72 (3)
N1—C7	1.3110 (17)	O3W—H32W	0.98 (3)
O1—B1—O6	109.01 (10)	C7—N1—H12	122.4 (11)
O1—B1—O10	109.67 (10)	H11—N1—H12	117.7 (16)
O6—B1—O10	110.02 (9)	C7—N2—H21	119.9 (11)
O1—B1—O5	110.83 (9)	C7—N2—H22	121.9 (11)
O6—B1—O5	107.59 (10)	H21—N2—H22	117.4 (15)
O10—B1—O5	109.70 (10)	C6—C1—C2	119.52 (13)
B2—O1—B1	124.25 (10)	C6—C1—C7	120.52 (12)
O2—B2—O1	118.37 (12)	C2—C1—C7	119.97 (12)
O2—B2—O3	120.85 (11)	C3—C2—C1	119.80 (14)
O1—B2—O3	120.77 (11)	C3—C2—H2B	120.1
B2—O2—H2	113.3 (13)	C1—C2—H2B	120.1
B3—O3—B2	118.95 (10)	C4—C3—C2	120.24 (14)
B3—O4—H4	113.7 (13)	C4—C3—H3	119.9
O5—B3—O4	122.84 (12)	C2—C3—H3	119.9
O5—B3—O3	120.79 (11)	C3—C4—C5	120.45 (14)
O4—B3—O3	116.37 (11)	C3—C4—H4B	119.8
B3—O5—B1	124.05 (10)	C5—C4—H4B	119.8
B4—O6—B1	123.03 (10)	C4—C5—C6	119.90 (15)
B4—O7—H7	111.2 (13)	C4—C5—H5	120.0
B5—O8—B4	119.26 (10)	C6—C5—H5	120.0
O7—B4—O6	122.12 (12)	C5—C6—C1	120.09 (14)
O7—B4—O8	117.66 (11)	C5—C6—H6	120.0
O6—B4—O8	120.22 (13)	C1—C6—H6	120.0
B5—O9—H9	111.6 (13)	N1—C7—N2	119.55 (13)
B5—O10—B1	122.74 (11)	N1—C7—C1	120.16 (12)
O10—B5—O9	123.50 (13)	N2—C7—C1	120.28 (12)
O10—B5—O8	120.89 (11)	C7A—N1A—H11A	116.7 (12)
O9—B5—O8	115.61 (11)	C7A—N1A—H12A	119.3 (12)
O10A—B1A—O5A	109.86 (11)	H11A—N1A—H12A	122.5 (17)
O10A—B1A—O6A	111.11 (9)	C7A—N2A—H21A	122.3 (13)
O5A—B1A—O6A	106.98 (10)	C7A—N2A—H22A	121.0 (11)
O10A—B1A—O1A	108.47 (10)	H21A—N2A—H22A	116.7 (17)
O5A—B1A—O1A	110.50 (9)	C2A—C1A—C6A	119.51 (13)
O6A—B1A—O1A	109.93 (11)	C2A—C1A—C7A	119.90 (13)
B2A—O1A—B1A	122.37 (10)	C6A—C1A—C7A	120.59 (14)
O1A—B2A—O2A	122.20 (13)	C1A—C2A—C3A	120.39 (16)
O1A—B2A—O3A	121.68 (11)	C1A—C2A—H23A	119.8
O2A—B2A—O3A	116.12 (11)	C3A—C2A—H23A	119.8
B2A—O2A—H2A	112.4 (12)	C4A—C3A—C2A	119.79 (18)
B2A—O3A—B3A	119.19 (10)	C4A—C3A—H3A	120.1
B3A—O4A—H4A	115.1 (14)	C2A—C3A—H3A	120.1
O4A—B3A—O5A	121.78 (12)	C5A—C4A—C3A	120.32 (15)
O4A—B3A—O3A	117.46 (11)	C5A—C4A—H41A	119.8
O5A—B3A—O3A	120.76 (13)	C3A—C4A—H41A	119.8
B3A—O5A—B1A	122.46 (10)	C4A—C5A—C6A	120.38 (15)
B4A—O6A—B1A	121.68 (10)	C4A—C5A—H5A	119.8
B4A—O7A—H7A	113.7 (14)	C6A—C5A—H5A	119.8
B4A—O8A—B5A	118.13 (11)	C5A—C6A—C1A	119.59 (16)
O6A—B4A—O7A	123.06 (13)	C5A—C6A—H6A	120.2
O6A—B4A—O8A	121.13 (13)	C1A—C6A—H6A	120.2
O7A—B4A—O8A	115.80 (13)	N2A—C7A—N1A	120.97 (14)
B5A—O9A—H9A	112.3 (13)	N2A—C7A—C1A	120.29 (13)
B5A—O10A—B1A	121.15 (11)	N1A—C7A—C1A	118.74 (14)
O10A—B5A—O9A	119.12 (13)	H11W—O1W—H12W	107 (2)
O10A—B5A—O8A	121.56 (12)	H21W—O2W—H22W	102.8 (18)
O9A—B5A—O8A	119.33 (12)	H31W—O3W—H32W	118 (3)
C7—N1—H11	119.8 (11)
O6—B1—O1—B2	−124.83 (12)	O6A—B1A—O5A—B3A	99.35 (13)
O10—B1—O1—B2	114.67 (13)	O1A—B1A—O5A—B3A	−20.30 (16)
O5—B1—O1—B2	−6.59 (17)	O10A—B1A—O6A—B4A	17.60 (18)
B1—O1—B2—O2	−177.28 (12)	O5A—B1A—O6A—B4A	137.51 (13)
B1—O1—B2—O3	4.01 (19)	O1A—B1A—O6A—B4A	−102.48 (14)
O2—B2—O3—B3	−177.04 (12)	B1A—O6A—B4A—O7A	−177.91 (16)
O1—B2—O3—B3	1.64 (19)	B1A—O6A—B4A—O8A	1.3 (2)
B2—O3—B3—O5	−3.89 (19)	B5A—O8A—B4A—O6A	−17.0 (2)
B2—O3—B3—O4	176.05 (12)	B5A—O8A—B4A—O7A	162.24 (15)
O4—B3—O5—B1	−179.28 (12)	O5A—B1A—O10A—B5A	−140.66 (12)
O3—B3—O5—B1	0.7 (2)	O6A—B1A—O10A—B5A	−22.48 (17)
O1—B1—O5—B3	4.27 (17)	O1A—B1A—O10A—B5A	98.46 (13)
O6—B1—O5—B3	123.36 (12)	B1A—O10A—B5A—O9A	−170.58 (12)
O10—B1—O5—B3	−116.98 (13)	B1A—O10A—B5A—O8A	8.9 (2)
O1—B1—O6—B4	−141.66 (11)	B4A—O8A—B5A—O10A	12.0 (2)
O10—B1—O6—B4	−21.37 (16)	B4A—O8A—B5A—O9A	−168.55 (14)
O5—B1—O6—B4	98.08 (13)	C6—C1—C2—C3	−0.5 (2)
B1—O6—B4—O7	−169.70 (12)	C7—C1—C2—C3	179.67 (13)
B1—O6—B4—O8	10.48 (19)	C1—C2—C3—C4	0.0 (2)
B5—O8—B4—O7	−173.33 (12)	C2—C3—C4—C5	0.7 (3)
B5—O8—B4—O6	6.49 (19)	C3—C4—C5—C6	−0.9 (3)
O1—B1—O10—B5	137.70 (12)	C4—C5—C6—C1	0.3 (2)
O6—B1—O10—B5	17.80 (16)	C2—C1—C6—C5	0.4 (2)
O5—B1—O10—B5	−100.36 (13)	C7—C1—C6—C5	−179.81 (14)
B1—O10—B5—O9	176.52 (12)	C6—C1—C7—N1	−151.51 (14)
B1—O10—B5—O8	−3.40 (19)	C2—C1—C7—N1	28.3 (2)
B4—O8—B5—O10	−9.94 (19)	C6—C1—C7—N2	28.5 (2)
B4—O8—B5—O9	170.13 (12)	C2—C1—C7—N2	−151.66 (13)
O10A—B1A—O1A—B2A	133.89 (12)	C6A—C1A—C2A—C3A	0.8 (2)
O5A—B1A—O1A—B2A	13.41 (16)	C7A—C1A—C2A—C3A	−178.70 (15)
O6A—B1A—O1A—B2A	−104.44 (13)	C1A—C2A—C3A—C4A	0.6 (3)
B1A—O1A—B2A—O2A	179.00 (11)	C2A—C3A—C4A—C5A	−1.3 (3)
B1A—O1A—B2A—O3A	−0.22 (19)	C3A—C4A—C5A—C6A	0.5 (3)
O1A—B2A—O3A—B3A	−8.04 (19)	C4A—C5A—C6A—C1A	0.8 (2)
O2A—B2A—O3A—B3A	172.69 (11)	C2A—C1A—C6A—C5A	−1.5 (2)
B2A—O3A—B3A—O4A	−179.36 (12)	C7A—C1A—C6A—C5A	177.97 (13)
B2A—O3A—B3A—O5A	1.16 (19)	C2A—C1A—C7A—N2A	147.16 (16)
O4A—B3A—O5A—B1A	−165.33 (12)	C6A—C1A—C7A—N2A	−32.3 (2)
O3A—B3A—O5A—B1A	14.13 (19)	C2A—C1A—C7A—N1A	−31.8 (2)
O10A—B1A—O5A—B3A	−139.94 (12)	C6A—C1A—C7A—N1A	148.75 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3i	0.83 (2)	2.04 (2)	2.8562 (13)	167.4 (18)
O4—H4···O6Aii	0.87 (2)	2.00 (2)	2.8361 (13)	161.3 (18)
O7—H7···O5Aiii	0.89 (2)	1.80 (2)	2.6877 (13)	177 (2)
O9—H9···O1Aiv	0.87 (2)	1.91 (2)	2.7784 (14)	174.6 (19)
O2A—H2A···O10iv	0.87 (2)	1.84 (2)	2.7050 (14)	174.5 (17)
O4A—H4A···O6iii	0.89 (2)	1.79 (2)	2.6735 (13)	178 (2)
O7A—H7A···O5ii	0.92 (2)	1.93 (2)	2.8085 (15)	160 (2)
O9A—H9A···O2W	0.87 (2)	2.18 (2)	2.9474 (16)	147.4 (18)
N1—H11···O1W	0.870 (18)	2.059 (18)	2.8756 (18)	156.0 (16)
N1—H12···O2Av	0.872 (18)	1.996 (18)	2.8484 (15)	165.7 (15)
N2—H21···O1W	0.893 (17)	2.330 (17)	3.0892 (18)	142.8 (14)
N2—H22···O4A	0.858 (17)	2.025 (18)	2.8772 (16)	172.0 (15)
N1A—H11A···O10A	0.869 (19)	2.238 (19)	3.0084 (18)	147.7 (16)
N1A—H12A···O8	0.892 (19)	2.12 (2)	2.9646 (17)	157.4 (16)
N2A—H21A···O2Wiv	0.86 (2)	2.01 (2)	2.8703 (18)	175.0 (18)
N2A—H22A···O9	0.891 (19)	2.181 (19)	3.0717 (16)	178.4 (16)
O1W—H11W···O1vi	0.82 (2)	2.10 (2)	2.9180 (15)	173 (2)
O1W—H12W···O4vii	0.85 (2)	2.22 (2)	3.0033 (18)	153 (2)
O2W—H21W···O3W	0.93 (2)	1.92 (2)	2.8199 (19)	163 (2)
O2W—H22W···O7viii	0.91 (2)	1.90 (2)	2.8016 (14)	169.3 (19)
O3W—H31W···O3Wix	0.72 (3)	2.488 (10)	3.003 (3)	130.5 (17)
O3W—H32W···O7A	0.98 (3)	2.05 (3)	2.983 (2)	159 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3i	0.83 (2)	2.04 (2)	2.8562 (13)	167.4 (18)
O4—H4⋯O6Aii	0.87 (2)	2.00 (2)	2.8361 (13)	161.3 (18)
O7—H7⋯O5Aiii	0.89 (2)	1.80 (2)	2.6877 (13)	177 (2)
O9—H9⋯O1Aiv	0.87 (2)	1.91 (2)	2.7784 (14)	174.6 (19)
O2A—H2A⋯O10iv	0.87 (2)	1.84 (2)	2.7050 (14)	174.5 (17)
O4A—H4A⋯O6iii	0.89 (2)	1.79 (2)	2.6735 (13)	178 (2)
O7A—H7A⋯O5ii	0.92 (2)	1.93 (2)	2.8085 (15)	160 (2)
O9A—H9A⋯O2W	0.87 (2)	2.18 (2)	2.9474 (16)	147.4 (18)
N1—H11⋯O1W	0.870 (18)	2.059 (18)	2.8756 (18)	156.0 (16)
N1—H12⋯O2Av	0.872 (18)	1.996 (18)	2.8484 (15)	165.7 (15)
N2—H21⋯O1W	0.893 (17)	2.330 (17)	3.0892 (18)	142.8 (14)
N2—H22⋯O4A	0.858 (17)	2.025 (18)	2.8772 (16)	172.0 (15)
N1A—H11A⋯O10A	0.869 (19)	2.238 (19)	3.0084 (18)	147.7 (16)
N1A—H12A⋯O8	0.892 (19)	2.12 (2)	2.9646 (17)	157.4 (16)
N2A—H21A⋯O2Wiv	0.86 (2)	2.01 (2)	2.8703 (18)	175.0 (18)
N2A—H22A⋯O9	0.891 (19)	2.181 (19)	3.0717 (16)	178.4 (16)
O1W—H11W⋯O1vi	0.82 (2)	2.10 (2)	2.9180 (15)	173 (2)
O1W—H12W⋯O4vii	0.85 (2)	2.22 (2)	3.0033 (18)	153 (2)
O2W—H21W⋯O3W	0.93 (2)	1.92 (2)	2.8199 (19)	163 (2)
O2W—H22W⋯O7viii	0.91 (2)	1.90 (2)	2.8016 (14)	169.3 (19)
O3W—H31W⋯O3Wix	0.72 (3)	2.488 (10)	3.003 (3)	130.5 (17)
O3W—H32W⋯O7A	0.98 (3)	2.05 (3)	2.983 (2)	159 (2)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) ; (ix) .