Tetra-butyl-ammonium hydrogen phenyl-arsonate-phenyl-arsonic acid (1/1).

The structure of the title salt adduct, (C(4)H(9))(4)N(+)·C(6)H(5)AsO(3)H(-)·C(6)H(5)AsO(3)H(2), features chains along the a axis comprising alternating hydrogen phenyl-arsonate anions and phenyl-arsonic acid mol-ecules linked by O-H⋯O hydrogen bonds.

Related literature

For similar structures containing bulky hydro­phobic cations and hydrogen-bonded chains of hydrogen(aryl­phospho­nate)/aryl­phospho­nic acid, see: Clarke et al. (2005 ▶); Latham et al. (2007 ▶, 2008 ▶). For hybrid organic–inorganic polyoxidometalate frameworks including aryl­arsonic acid ligands, see: Breen, Clérac et al. (2012 ▶); Breen, Zhang et al. (2012 ▶); Zhang & Schmitt (2011 ▶); Onet et al. (2011 ▶); Breen & Schmitt (2008 ▶).

Experimental

Crystal data

C16H36N+·C6H6AsO3 −·C6H7AsO3

M = 645.52

Triclinic,

a = 9.035 (2) Å

b = 10.137 (3) Å

c = 18.789 (5) Å

α = 94.005 (5)°

β = 97.749 (4)°

γ = 114.289 (4)°

V = 1539.2 (7) Å3

Z = 2

Mo Kα radiation

μ = 2.21 mm−1

T = 120 K

0.5 × 0.3 × 0.1 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.291, T max = 0.809

15253 measured reflections

7513 independent reflections

6769 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.070

S = 1.03

7513 reflections

530 parameters

All H-atom parameters refined

Δρmax = 0.61 e Å−3

Δρmin = −0.71 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶) and OLEX2 (Dolomanov et al., 2009 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and OLEX2; molecular graphics: OLEX2; software used to prepare material for publication: SHELXL97 and OLEX2.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812035362/tk5138sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035362/tk5138Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035362/tk5138Isup3.cdx

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

C16H36N+·C6H6AsO3−·C6H7AsO3	Z = 2
Mr = 645.52	F(000) = 676
Triclinic, P1	Dx = 1.393 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.035 (2) Å	Cell parameters from 232 reflections
b = 10.137 (3) Å	θ = 2.3–27.2°
c = 18.789 (5) Å	µ = 2.21 mm−1
α = 94.005 (5)°	T = 120 K
β = 97.749 (4)°	Block, colourless
γ = 114.289 (4)°	0.5 × 0.3 × 0.1 mm
V = 1539.2 (7) Å3

Bruker SMART APEX diffractometer	7513 independent reflections
Radiation source: fine-focus sealed tube	6769 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 28.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −12→12
Tmin = 0.291, Tmax = 0.809	k = −13→13
15253 measured reflections	l = −23→24

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026	Hydrogen site location: difference Fourier map
wR(F2) = 0.070	All H-atom parameters refined
S = 1.03	w = 1/[σ2(Fo2) + (0.0421P)2 + 0.2175P] where P = (Fo2 + 2Fc2)/3
7513 reflections	(Δ/σ)max = 0.001
530 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.71 e Å−3

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
As1	0.983720 (17)	0.434497 (16)	0.191058 (8)	0.01665 (5)
O11	0.84503 (14)	0.41025 (14)	0.24937 (6)	0.0253 (2)
H11	0.799 (3)	0.458 (3)	0.2399 (15)	0.060 (8)*
O12	1.13065 (13)	0.60598 (11)	0.20887 (6)	0.0208 (2)
O13	1.05793 (13)	0.31108 (12)	0.20416 (6)	0.0218 (2)
N1	1.04658 (14)	0.94499 (13)	0.26111 (7)	0.0157 (2)
C11	0.86611 (17)	0.39575 (16)	0.09453 (8)	0.0193 (3)
C12	0.9186 (2)	0.33147 (18)	0.04140 (9)	0.0248 (3)
H12	1.011 (3)	0.312 (2)	0.0525 (12)	0.036 (5)*
C13	0.8426 (2)	0.3079 (2)	−0.02994 (10)	0.0301 (4)
H13	0.880 (2)	0.268 (2)	−0.0679 (11)	0.030 (5)*
C14	0.7155 (2)	0.3475 (2)	−0.04864 (10)	0.0322 (4)
H14	0.674 (3)	0.334 (2)	−0.0930 (12)	0.034 (6)*
C15	0.6630 (2)	0.4103 (2)	0.00444 (11)	0.0379 (4)
H15	0.571 (3)	0.437 (2)	−0.0117 (12)	0.044 (6)*
C16	0.7377 (2)	0.4351 (2)	0.07646 (10)	0.0292 (4)
H16	0.707 (3)	0.473 (2)	0.1076 (12)	0.034 (6)*
C31	1.06254 (18)	0.83454 (16)	0.30861 (8)	0.0171 (3)
H31A	0.950 (2)	0.764 (2)	0.3068 (10)	0.018 (4)*
H31B	1.115 (2)	0.790 (2)	0.2842 (10)	0.019 (4)*
C32	1.1517 (2)	0.89580 (18)	0.38583 (9)	0.0222 (3)
H32A	1.089 (2)	0.926 (2)	0.4123 (11)	0.026 (5)*
H32B	1.253 (2)	0.982 (2)	0.3874 (10)	0.021 (4)*
C33	1.1868 (2)	0.7791 (2)	0.42250 (10)	0.0281 (3)
H33A	1.261 (3)	0.751 (2)	0.3952 (12)	0.035 (5)*
H33B	1.241 (3)	0.822 (2)	0.4668 (12)	0.034 (5)*
C34	1.0341 (3)	0.6426 (2)	0.42641 (12)	0.0406 (5)
H34A	1.060 (3)	0.580 (3)	0.4569 (13)	0.045 (6)*
H34B	0.988 (3)	0.590 (3)	0.3788 (15)	0.050 (7)*
H34C	0.962 (3)	0.675 (2)	0.4455 (12)	0.038 (6)*
C41	0.93601 (17)	0.85567 (16)	0.19096 (8)	0.0167 (3)
H41A	0.835 (2)	0.799 (2)	0.2031 (9)	0.015 (4)*
H41B	0.984 (2)	0.7952 (19)	0.1749 (9)	0.014 (4)*
C42	0.90926 (19)	0.94151 (17)	0.13157 (8)	0.0199 (3)
H42A	0.870 (2)	1.012 (2)	0.1467 (10)	0.023 (5)*
H42B	1.014 (3)	1.004 (2)	0.1162 (12)	0.037 (6)*
C43	0.7900 (2)	0.8353 (2)	0.06719 (9)	0.0288 (3)
H43A	0.828 (3)	0.767 (3)	0.0487 (12)	0.044 (6)*
H43B	0.692 (3)	0.781 (3)	0.0840 (12)	0.039 (6)*
C44	0.7506 (2)	0.9096 (2)	0.00493 (10)	0.0334 (4)
H44A	0.677 (3)	0.839 (3)	−0.0324 (15)	0.054 (7)*
H44B	0.847 (3)	0.971 (3)	−0.0122 (13)	0.050 (7)*
H44C	0.698 (3)	0.973 (3)	0.0199 (13)	0.047 (6)*
C51	1.21333 (17)	1.05089 (16)	0.24719 (8)	0.0180 (3)
H51A	1.280 (2)	1.095 (2)	0.2939 (10)	0.018 (4)*
H51B	1.192 (2)	1.121 (2)	0.2232 (10)	0.016 (4)*
C52	1.30155 (18)	0.98468 (17)	0.20316 (9)	0.0209 (3)
H52A	1.237 (2)	0.947 (2)	0.1528 (11)	0.026 (5)*
H52B	1.310 (2)	0.904 (2)	0.2218 (11)	0.024 (5)*
C53	1.47142 (19)	1.10091 (18)	0.19840 (10)	0.0224 (3)
H53A	1.462 (2)	1.176 (2)	0.1776 (11)	0.027 (5)*
H53B	1.530 (2)	1.133 (2)	0.2446 (11)	0.022 (5)*
C54	1.5617 (2)	1.0398 (2)	0.15297 (11)	0.0288 (4)
H54A	1.664 (3)	1.110 (2)	0.1490 (12)	0.035 (5)*
H54B	1.506 (3)	1.010 (2)	0.1048 (13)	0.036 (6)*
H54C	1.567 (3)	0.956 (3)	0.1718 (13)	0.044 (6)*
C61	0.97536 (18)	1.03791 (16)	0.29762 (8)	0.0182 (3)
H61A	0.972 (2)	1.107 (2)	0.2659 (10)	0.017 (4)*
H61B	1.062 (2)	1.094 (2)	0.3409 (10)	0.018 (4)*
C62	0.81020 (19)	0.95365 (18)	0.31980 (9)	0.0213 (3)
H62A	0.810 (2)	0.882 (2)	0.3471 (11)	0.029 (5)*
H62B	0.725 (2)	0.900 (2)	0.2774 (11)	0.028 (5)*
C63	0.7615 (2)	1.0596 (2)	0.36162 (10)	0.0274 (3)
H63A	0.845 (3)	1.116 (2)	0.4042 (12)	0.037 (6)*
H63B	0.765 (3)	1.141 (3)	0.3339 (13)	0.041 (6)*
C64	0.5945 (2)	0.9811 (2)	0.38350 (11)	0.0338 (4)
H64A	0.559 (3)	1.040 (3)	0.4060 (13)	0.044 (6)*
H64B	0.599 (3)	0.917 (3)	0.4161 (16)	0.070 (9)*
H64C	0.512 (3)	0.928 (3)	0.3427 (13)	0.043 (6)*
As2	0.478325 (17)	0.517474 (16)	0.248301 (8)	0.01779 (5)
O21	0.34772 (15)	0.38567 (13)	0.17947 (6)	0.0231 (2)
H21	0.260 (4)	0.365 (3)	0.1849 (15)	0.062 (9)*
O22	0.42750 (14)	0.66150 (12)	0.24787 (7)	0.0251 (2)
H22	0.317 (5)	0.641 (4)	0.236 (2)	0.112 (13)*
O23	0.67109 (13)	0.56498 (13)	0.23897 (7)	0.0285 (3)
C21	0.43938 (19)	0.44095 (16)	0.33777 (8)	0.0211 (3)
C22	0.3014 (2)	0.4323 (2)	0.36604 (9)	0.0287 (3)
H22A	0.232 (3)	0.472 (2)	0.3414 (12)	0.037 (6)*
C23	0.2713 (3)	0.3712 (2)	0.42920 (11)	0.0416 (5)
H23	0.196 (4)	0.366 (4)	0.4490 (18)	0.081 (11)*
C24	0.3770 (3)	0.3205 (2)	0.46396 (11)	0.0476 (6)
H24	0.362 (3)	0.277 (3)	0.5068 (16)	0.066 (8)*
C25	0.5133 (3)	0.3297 (2)	0.43635 (11)	0.0456 (5)
H25	0.585 (3)	0.299 (3)	0.4570 (15)	0.059 (8)*
C26	0.5467 (2)	0.38999 (19)	0.37277 (10)	0.0312 (4)
H26	0.638 (3)	0.400 (2)	0.3565 (11)	0.031 (5)*

	U11	U22	U33	U12	U13	U23
As1	0.01668 (8)	0.01561 (8)	0.01751 (8)	0.00714 (6)	0.00178 (6)	0.00218 (6)
O11	0.0238 (5)	0.0326 (7)	0.0222 (6)	0.0133 (5)	0.0079 (4)	0.0065 (5)
O12	0.0195 (5)	0.0149 (5)	0.0273 (6)	0.0079 (4)	0.0016 (4)	−0.0001 (4)
O13	0.0214 (5)	0.0158 (5)	0.0293 (6)	0.0094 (4)	0.0017 (4)	0.0055 (4)
N1	0.0160 (5)	0.0137 (6)	0.0172 (6)	0.0061 (5)	0.0031 (4)	0.0024 (5)
C11	0.0193 (6)	0.0153 (7)	0.0198 (7)	0.0046 (6)	0.0014 (5)	0.0028 (6)
C12	0.0269 (7)	0.0247 (8)	0.0227 (8)	0.0115 (7)	0.0032 (6)	0.0018 (6)
C13	0.0365 (9)	0.0262 (9)	0.0222 (8)	0.0086 (7)	0.0055 (7)	−0.0014 (7)
C14	0.0342 (9)	0.0303 (9)	0.0210 (8)	0.0062 (7)	−0.0058 (7)	0.0014 (7)
C15	0.0343 (9)	0.0462 (11)	0.0337 (10)	0.0229 (9)	−0.0086 (8)	0.0001 (9)
C16	0.0276 (8)	0.0351 (9)	0.0263 (9)	0.0178 (7)	−0.0015 (7)	−0.0032 (7)
C31	0.0195 (6)	0.0144 (7)	0.0184 (7)	0.0080 (6)	0.0032 (5)	0.0036 (5)
C32	0.0258 (7)	0.0216 (8)	0.0187 (7)	0.0109 (7)	0.0002 (6)	0.0016 (6)
C33	0.0337 (9)	0.0297 (9)	0.0212 (8)	0.0151 (7)	−0.0009 (7)	0.0068 (7)
C34	0.0480 (11)	0.0385 (11)	0.0358 (11)	0.0149 (10)	0.0126 (9)	0.0215 (9)
C41	0.0168 (6)	0.0161 (7)	0.0157 (7)	0.0059 (6)	0.0019 (5)	0.0016 (5)
C42	0.0205 (7)	0.0211 (7)	0.0185 (7)	0.0089 (6)	0.0041 (6)	0.0045 (6)
C43	0.0336 (9)	0.0290 (9)	0.0204 (8)	0.0125 (8)	−0.0028 (7)	0.0023 (7)
C44	0.0339 (9)	0.0449 (11)	0.0219 (8)	0.0178 (9)	0.0008 (7)	0.0086 (8)
C51	0.0171 (6)	0.0135 (7)	0.0211 (7)	0.0043 (5)	0.0036 (5)	0.0025 (6)
C52	0.0171 (6)	0.0183 (7)	0.0263 (8)	0.0066 (6)	0.0049 (6)	0.0009 (6)
C53	0.0186 (7)	0.0187 (7)	0.0289 (9)	0.0066 (6)	0.0054 (6)	0.0038 (7)
C54	0.0220 (7)	0.0248 (8)	0.0429 (11)	0.0109 (7)	0.0125 (7)	0.0068 (8)
C61	0.0202 (6)	0.0162 (7)	0.0201 (7)	0.0093 (6)	0.0044 (6)	0.0019 (6)
C62	0.0210 (7)	0.0210 (7)	0.0246 (8)	0.0107 (6)	0.0065 (6)	0.0035 (6)
C63	0.0237 (7)	0.0305 (9)	0.0292 (9)	0.0140 (7)	0.0049 (7)	−0.0040 (7)
C64	0.0258 (8)	0.0432 (11)	0.0339 (10)	0.0170 (8)	0.0078 (7)	−0.0044 (9)
As2	0.01481 (8)	0.01589 (8)	0.02339 (9)	0.00662 (6)	0.00487 (6)	0.00389 (6)
O21	0.0246 (6)	0.0215 (6)	0.0224 (6)	0.0101 (5)	0.0022 (5)	0.0002 (4)
O22	0.0236 (5)	0.0161 (5)	0.0366 (7)	0.0103 (5)	0.0028 (5)	0.0032 (5)
O23	0.0171 (5)	0.0243 (6)	0.0462 (7)	0.0081 (5)	0.0123 (5)	0.0083 (5)
C21	0.0233 (7)	0.0153 (7)	0.0203 (7)	0.0056 (6)	−0.0006 (6)	0.0005 (6)
C22	0.0272 (8)	0.0300 (9)	0.0212 (8)	0.0054 (7)	0.0033 (6)	−0.0007 (7)
C23	0.0475 (11)	0.0354 (11)	0.0253 (9)	0.0002 (9)	0.0123 (9)	−0.0008 (8)
C24	0.0809 (16)	0.0269 (10)	0.0188 (9)	0.0090 (10)	0.0026 (10)	0.0033 (7)
C25	0.0738 (15)	0.0286 (10)	0.0294 (10)	0.0248 (11)	−0.0150 (10)	−0.0004 (8)
C26	0.0371 (9)	0.0228 (8)	0.0309 (9)	0.0147 (7)	−0.0062 (7)	−0.0015 (7)

As1—O13	1.6625 (10)	C44—H44C	0.99 (2)
As1—O12	1.6723 (11)	C51—C52	1.520 (2)
As1—O11	1.7279 (11)	C51—H51A	0.956 (19)
As1—C11	1.9001 (16)	C51—H51B	0.941 (18)
O11—H11	0.77 (3)	C52—C53	1.522 (2)
N1—C41	1.5130 (18)	C52—H52A	1.00 (2)
N1—C61	1.5163 (17)	C52—H52B	0.94 (2)
N1—C51	1.5185 (18)	C53—C54	1.519 (2)
N1—C31	1.5194 (18)	C53—H53A	0.91 (2)
C11—C16	1.383 (2)	C53—H53B	0.91 (2)
C11—C12	1.392 (2)	C54—H54A	0.92 (2)
C12—C13	1.378 (2)	C54—H54B	0.94 (2)
C12—H12	0.94 (2)	C54—H54C	0.96 (2)
C13—C14	1.376 (3)	C61—C62	1.516 (2)
C13—H13	0.96 (2)	C61—H61A	0.954 (18)
C14—C15	1.383 (3)	C61—H61B	1.000 (18)
C14—H14	0.84 (2)	C62—C63	1.526 (2)
C15—C16	1.384 (3)	C62—H62A	0.92 (2)
C15—H15	1.00 (2)	C62—H62B	0.97 (2)
C16—H16	0.82 (2)	C63—C64	1.518 (2)
C31—C32	1.512 (2)	C63—H63A	0.98 (2)
C31—H31A	0.966 (19)	C63—H63B	1.00 (2)
C31—H31B	0.922 (18)	C64—H64A	0.89 (2)
C32—C33	1.529 (2)	C64—H64B	0.93 (3)
C32—H32A	0.929 (19)	C64—H64C	0.94 (2)
C32—H32B	0.96 (2)	As2—O23	1.6432 (11)
C33—C34	1.515 (3)	As2—O22	1.7013 (11)
C33—H33A	1.01 (2)	As2—O21	1.7030 (12)
C33—H33B	0.89 (2)	As2—C21	1.9153 (16)
C34—H34A	0.96 (3)	O21—H21	0.75 (3)
C34—H34B	0.95 (3)	O22—H22	0.93 (4)
C34—H34C	0.94 (2)	C21—C26	1.388 (2)
C41—C42	1.515 (2)	C21—C22	1.393 (2)
C41—H41A	0.930 (18)	C22—C23	1.385 (3)
C41—H41B	0.943 (17)	C22—H22A	0.96 (2)
C42—C43	1.515 (2)	C23—C24	1.372 (4)
C42—H42A	0.964 (19)	C23—H23	0.81 (3)
C42—H42B	1.00 (2)	C24—C25	1.371 (4)
C43—C44	1.515 (2)	C24—H24	0.94 (3)
C43—H43A	0.95 (2)	C25—C26	1.392 (3)
C43—H43B	0.94 (2)	C25—H25	0.88 (3)
C44—H44A	0.93 (3)	C26—H26	0.89 (2)
C44—H44B	0.95 (3)
O13—As1—O12	112.71 (6)	H44A—C44—H44C	108 (2)
O13—As1—O11	106.12 (6)	H44B—C44—H44C	106 (2)
O12—As1—O11	109.42 (6)	N1—C51—C52	115.86 (12)
O13—As1—C11	109.58 (6)	N1—C51—H51A	106.0 (11)
O12—As1—C11	110.72 (6)	C52—C51—H51A	109.5 (10)
O11—As1—C11	108.09 (6)	N1—C51—H51B	104.9 (11)
As1—O11—H11	108 (2)	C52—C51—H51B	110.5 (10)
C41—N1—C61	111.98 (11)	H51A—C51—H51B	109.9 (15)
C41—N1—C51	110.79 (11)	C51—C52—C53	109.94 (12)
C61—N1—C51	105.97 (11)	C51—C52—H52A	109.8 (10)
C41—N1—C31	105.49 (11)	C53—C52—H52A	108.1 (11)
C61—N1—C31	111.07 (11)	C51—C52—H52B	112.6 (12)
C51—N1—C31	111.65 (11)	C53—C52—H52B	110.7 (12)
C16—C11—C12	120.67 (15)	H52A—C52—H52B	105.6 (16)
C16—C11—As1	121.87 (12)	C54—C53—C52	111.50 (14)
C12—C11—As1	117.40 (11)	C54—C53—H53A	107.9 (12)
C13—C12—C11	119.57 (15)	C52—C53—H53A	110.2 (12)
C13—C12—H12	119.0 (13)	C54—C53—H53B	109.1 (11)
C11—C12—H12	121.2 (13)	C52—C53—H53B	107.3 (12)
C14—C13—C12	120.28 (16)	H53A—C53—H53B	110.8 (17)
C14—C13—H13	118.4 (12)	C53—C54—H54A	112.0 (13)
C12—C13—H13	121.2 (12)	C53—C54—H54B	111.1 (13)
C13—C14—C15	119.90 (17)	H54A—C54—H54B	103.3 (19)
C13—C14—H14	117.8 (14)	C53—C54—H54C	109.8 (14)
C15—C14—H14	122.3 (14)	H54A—C54—H54C	112.9 (19)
C14—C15—C16	120.79 (17)	H54B—C54—H54C	107.5 (19)
C14—C15—H15	117.1 (13)	C62—C61—N1	115.27 (12)
C16—C15—H15	122.1 (13)	C62—C61—H61A	112.6 (10)
C11—C16—C15	118.79 (16)	N1—C61—H61A	106.8 (10)
C11—C16—H16	120.8 (15)	C62—C61—H61B	111.0 (10)
C15—C16—H16	120.4 (15)	N1—C61—H61B	103.2 (10)
C32—C31—N1	115.79 (12)	H61A—C61—H61B	107.2 (15)
C32—C31—H31A	111.6 (11)	C61—C62—C63	109.42 (13)
N1—C31—H31A	104.5 (11)	C61—C62—H62A	112.9 (12)
C32—C31—H31B	111.6 (11)	C63—C62—H62A	110.1 (12)
N1—C31—H31B	104.9 (11)	C61—C62—H62B	110.8 (12)
H31A—C31—H31B	107.8 (15)	C63—C62—H62B	109.8 (11)
C31—C32—C33	109.85 (13)	H62A—C62—H62B	103.7 (17)
C31—C32—H32A	110.9 (12)	C64—C63—C62	111.56 (15)
C33—C32—H32A	108.9 (12)	C64—C63—H63A	110.2 (13)
C31—C32—H32B	111.2 (11)	C62—C63—H63A	112.0 (12)
C33—C32—H32B	110.5 (11)	C64—C63—H63B	111.4 (13)
H32A—C32—H32B	105.5 (16)	C62—C63—H63B	111.7 (13)
C34—C33—C32	114.41 (15)	H63A—C63—H63B	99.4 (18)
C34—C33—H33A	109.1 (12)	C63—C64—H64A	114.5 (16)
C32—C33—H33A	108.3 (12)	C63—C64—H64B	110.2 (17)
C34—C33—H33B	110.2 (14)	H64A—C64—H64B	105 (2)
C32—C33—H33B	105.8 (14)	C63—C64—H64C	111.0 (14)
H33A—C33—H33B	108.9 (18)	H64A—C64—H64C	106 (2)
C33—C34—H34A	111.7 (14)	H64B—C64—H64C	109 (2)
C33—C34—H34B	108.6 (15)	O23—As2—O22	111.86 (6)
H34A—C34—H34B	108 (2)	O23—As2—O21	110.46 (6)
C33—C34—H34C	105.8 (14)	O22—As2—O21	107.93 (6)
H34A—C34—H34C	110 (2)	O23—As2—C21	110.94 (7)
H34B—C34—H34C	112 (2)	O22—As2—C21	107.65 (6)
N1—C41—C42	116.09 (12)	O21—As2—C21	107.84 (6)
N1—C41—H41A	106.0 (11)	As2—O21—H21	109 (2)
C42—C41—H41A	108.8 (11)	As2—O22—H22	118 (2)
N1—C41—H41B	105.8 (10)	C26—C21—C22	120.47 (17)
C42—C41—H41B	110.2 (10)	C26—C21—As2	119.45 (13)
H41A—C41—H41B	109.8 (15)	C22—C21—As2	120.05 (12)
C43—C42—C41	108.80 (13)	C23—C22—C21	119.34 (18)
C43—C42—H42A	110.4 (11)	C23—C22—H22A	122.5 (13)
C41—C42—H42A	113.6 (11)	C21—C22—H22A	118.1 (13)
C43—C42—H42B	109.7 (13)	C24—C23—C22	120.4 (2)
C41—C42—H42B	112.0 (13)	C24—C23—H23	116 (2)
H42A—C42—H42B	102.2 (17)	C22—C23—H23	124 (2)
C44—C43—C42	113.39 (16)	C25—C24—C23	120.3 (2)
C44—C43—H43A	107.8 (14)	C25—C24—H24	115.5 (17)
C42—C43—H43A	112.9 (14)	C23—C24—H24	124.2 (17)
C44—C43—H43B	108.8 (14)	C24—C25—C26	120.7 (2)
C42—C43—H43B	106.7 (14)	C24—C25—H25	123.4 (18)
H43A—C43—H43B	106.9 (19)	C26—C25—H25	115.9 (18)
C43—C44—H44A	109.2 (16)	C21—C26—C25	118.77 (19)
C43—C44—H44B	112.1 (15)	C21—C26—H26	120.8 (14)
H44A—C44—H44B	110 (2)	C25—C26—H26	120.3 (14)
C43—C44—H44C	111.2 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11···O23	0.77 (3)	1.88 (3)	2.6375 (17)	166 (3)
O21—H21···O13i	0.75 (3)	1.78 (3)	2.5280 (17)	176 (3)
O22—H22···O12i	0.93 (4)	1.57 (4)	2.4936 (17)	176 (4)

Table 1

Selected bond lengths (Å)

As1—O13	1.6625 (10)
As1—O12	1.6723 (11)
As1—O11	1.7279 (11)
As1—C11	1.9001 (16)
As2—O23	1.6432 (11)
As2—O22	1.7013 (11)
As2—O21	1.7030 (12)
As2—C21	1.9153 (16)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O11—H11⋯O23	0.77 (3)	1.88 (3)	2.6375 (17)	166 (3)
O21—H21⋯O13i	0.75 (3)	1.78 (3)	2.5280 (17)	176 (3)
O22—H22⋯O12i	0.93 (4)	1.57 (4)	2.4936 (17)	176 (4)

Symmetry code: (i) .