cyclo-Tetra-μ-oxido-tetrakis­[3-nitro-4-hydroxy­phenyl­arsenic(III)]

Lloyd, N.C.; Nicholson, B.K.

doi:10.1107/S1600536807044728

Buy article online - an online subscription or single-article purchase is required to access this article.

cyclo-Tetra-μ-oxido-tetrakis[3-nitro-4-hydroxyphenylarsenic(III)]

N. C. Lloyd and B. K. Nicholson

The title compound, [As₄O₄(C₆H₄NO₃)₄], has an eight-membered As₄O₄ ring with a slightly twisted boat–chair conformation. The aryl groups complete the threefold coordination for each As atom. Each OH group forms a strong intramolecular O—H

O hydrogen bond to the adjacent NO₂ group, with only weak C—H

O, O

As [3.036 (6)–3.184 (6) Å] and O

O [2.921 (10)–2.930 (10) Å] interactions between tetramers.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044728/hy2082sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044728/hy2082Isup2.hkl Contains datablock I

CCDC reference: 663627

checkCIF report

Key indicators

Single-crystal X-ray study
T = 93 K
Mean (C-C) = 0.014 Å
R factor = 0.068
wR factor = 0.131
Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact  As2    ..  O12     ..       3.04 Ang.

Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.113
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.11
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.91 Ratio
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         14
PLAT430_ALERT_2_C Short Inter D...A Contact  O3     ..  N1      ..       2.88 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  As4    ..  O12     ..       3.16 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11    ..  O1      ..       2.65 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15    ..  O13     ..       2.70 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12    ..  O11     ..       2.61 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Aryl arsenoxides of empirical formula RAsO exist as either hydrates RAs(OH)₂ as for the 4-H₂NC₆H₄ example (Knock et al., 1995), or as cyclic (RAsO)_n where n = 4 for R = Me (DiMaio & Rheingold, 1991), Ph (Muller & Muhle, 1999), mesityl (Arif et al., 1987), or 3-F₃CC₆H₄ (Sun et al., 2005) and n = 5 for R = Et (Hausler & Sheldrick, 1997). The title compound, [3-O₂N-4-HOC₆H₃AsO]₄, also forms an eight-membered As₄O₄ ring which has a slightly twisted boat-chair conformation. The aryl groups complete the 3-coordination for each As atom. Average parameters are: As—O = 1.801 (6) Å, O—As—O = 98.8 (3)° and As—O—As = 121.3 (4)°. The OH group is internally H-bonded to the adjacent NO₂ group, so the intermolecular interactions between tetramers are weak C—H···O and O···.As ones. There are also some short intermolecular O···O interactions involving the NO₂ groups.

Related literature top

A related compound, (4-H₂NC₆H₄)As(OH)₂, was reported by Knock or Knoch et al. (1995). Other examples of cyclic (RAsO)_n are n = 4 for R = Me (DiMaio & Rheingold, 1991), Ph (Muller & Muhle, 1999), mesityl (Arif et al., 1987) or 3-F₃CC₆H₄ (Sun et al., 2005), and n = 5 for R = Et (Hausler & Sheldrick, 1997).

Experimental top

The title compound was prepared by hydrolysis of the dichloride 3-O₂N-4-HOC₆H₃AsCl₂, which in turn was prepared by reduction of 3-O₂N-4-HOC₆H₃AsO₃H₂ with SO₂ in conc HCl. Crystals suitable for X-ray analysis were obtained from an aqueous solution.

Structure description top

Computing details top

Data collection: SMART (Bruker 2001); cell refinement: SAINT (Bruker 2001); data reduction: SAINT (Bruker 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Dotted lines denote hydrogen bonds.

cyclo-Tetra-µ-oxido-tetra[3-nitro-4-hydroxyphenylarsenic(III)] top

Crystal data top

[As₄O₄(C₆H₄NO₃)₄]	F(000) = 1792
M_r = 916.09	D_x = 2.091 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4805 reflections
a = 7.1289 (2) Å	θ = 2–25°
b = 31.6743 (9) Å	µ = 4.64 mm⁻¹
c = 13.0217 (4) Å	T = 93 K
β = 98.286 (1)°	Needle, yellow
V = 2909.64 (15) Å³	0.16 × 0.10 × 0.05 mm
Z = 4

Data collection top

Siemens SMART CCD diffractometer	5490 independent reflections
Radiation source: fine-focus sealed tube	3294 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.114
φ and ω scans	θ_max = 25.7°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.524, T_max = 0.801	k = −38→38
16032 measured reflections	l = −11→15

Refinement top

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0328P)² + 6.0469P] where P = (F_o² + 2F_c²)/3
5490 reflections	(Δ/σ)_max = 0.001
433 parameters	Δρ_max = 1.03 e Å⁻³
0 restraints	Δρ_min = −0.91 e Å⁻³

Crystal data top

[As₄O₄(C₆H₄NO₃)₄]	V = 2909.64 (15) Å³
M_r = 916.09	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.1289 (2) Å	µ = 4.64 mm⁻¹
b = 31.6743 (9) Å	T = 93 K
c = 13.0217 (4) Å	0.16 × 0.10 × 0.05 mm
β = 98.286 (1)°

Data collection top

Siemens SMART CCD diffractometer	5490 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3294 reflections with I > 2σ(I)
T_min = 0.524, T_max = 0.801	R_int = 0.114
16032 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.08	Δρ_max = 1.03 e Å⁻³
5490 reflections	Δρ_min = −0.91 e Å⁻³
433 parameters

Special details top

Refinement. As only small needle crystals were available, the data set was weak and so the final agreement factors are higher than usual.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
As1	0.02562 (13)	0.64613 (3)	0.12402 (7)	0.0189 (2)
As2	−0.24608 (13)	0.60197 (3)	0.25665 (8)	0.0204 (2)
As3	0.29993 (13)	0.67460 (3)	0.31865 (8)	0.0212 (3)
As4	0.07624 (14)	0.61371 (3)	0.45063 (8)	0.0236 (3)
N1	−0.1904 (10)	0.7965 (2)	−0.0349 (7)	0.0242 (19)
N2	−0.3338 (12)	0.5235 (3)	−0.1123 (7)	0.034 (2)
N3	0.2923 (12)	0.8406 (3)	0.2570 (7)	0.039 (2)
N4	0.7762 (13)	0.5809 (3)	0.6360 (7)	0.034 (2)
O1	−0.2016 (8)	0.64360 (17)	0.1704 (5)	0.0197 (14)
O2	−0.0071 (8)	0.59444 (18)	0.3221 (5)	0.0216 (15)
O3	0.1553 (8)	0.66539 (18)	0.4188 (5)	0.0221 (15)
O4	0.1206 (8)	0.68753 (17)	0.2095 (5)	0.0197 (15)
O11	−0.2457 (8)	0.76047 (19)	−0.2455 (5)	0.0241 (15)
H11	−0.2551	0.7859	−0.2288	0.036*
O12	−0.2549 (8)	0.82023 (19)	−0.1079 (5)	0.0262 (16)
O13	−0.1622 (10)	0.8085 (2)	0.0547 (5)	0.0325 (18)
O21	−0.2054 (9)	0.4438 (2)	−0.0092 (6)	0.0377 (19)
H21	−0.2416	0.4477	−0.0728	0.057*
O22	−0.3260 (10)	0.4912 (2)	−0.1659 (6)	0.043 (2)
O23	−0.3879 (12)	0.5576 (2)	−0.1491 (6)	0.049 (2)
O31	0.4044 (10)	0.8558 (2)	0.4784 (6)	0.048 (2)
H31	0.3830	0.8736	0.4303	0.072*
O32	0.2570 (13)	0.8322 (2)	0.1640 (6)	0.057 (2)
O33	0.2920 (11)	0.8781 (2)	0.2897 (6)	0.052 (2)
O41	0.8297 (9)	0.5182 (2)	0.4778 (5)	0.0338 (18)
H41	0.9070	0.5263	0.5288	0.051*
O42	0.7476 (10)	0.6104 (2)	0.6930 (5)	0.040 (2)
O43	0.9213 (10)	0.5587 (2)	0.6485 (6)	0.044 (2)
C11	−0.0641 (12)	0.6837 (3)	0.0105 (7)	0.019 (2)
C12	−0.0898 (12)	0.7266 (3)	0.0266 (7)	0.020 (2)
H12	−0.0634	0.7383	0.0944	0.024*
C13	−0.1554 (12)	0.7524 (3)	−0.0587 (7)	0.017 (2)
C14	−0.1879 (12)	0.7370 (3)	−0.1586 (7)	0.021 (2)
C15	−0.1662 (12)	0.6946 (3)	−0.1739 (7)	0.021 (2)
H15	−0.1932	0.6832	−0.2420	0.026*
C16	−0.1051 (12)	0.6679 (3)	−0.0911 (7)	0.022 (2)
H16	−0.0908	0.6385	−0.1032	0.026*
C21	−0.2211 (12)	0.5540 (3)	0.1643 (7)	0.019 (2)
C22	−0.2801 (12)	0.5560 (3)	0.0605 (7)	0.022 (2)
H22	−0.3236	0.5820	0.0293	0.027*
C23	−0.2766 (12)	0.5194 (3)	−0.0008 (7)	0.021 (2)
C24	−0.2126 (13)	0.4805 (3)	0.0424 (8)	0.028 (2)
C25	−0.1569 (13)	0.4790 (3)	0.1489 (8)	0.027 (2)
H25	−0.1170	0.4529	0.1811	0.032*
C26	−0.1591 (13)	0.5148 (3)	0.2082 (8)	0.025 (2)
H26	−0.1177	0.5132	0.2808	0.030*
C31	0.3370 (12)	0.7330 (3)	0.3635 (8)	0.026 (2)
C32	0.3039 (12)	0.7657 (3)	0.2948 (9)	0.028 (3)
H32	0.2640	0.7603	0.2232	0.034*
C33	0.3301 (13)	0.8084 (3)	0.3322 (9)	0.034 (3)
C34	0.3886 (13)	0.8159 (4)	0.4376 (8)	0.033 (3)
C35	0.4198 (13)	0.7831 (4)	0.5059 (9)	0.038 (3)
H35	0.4586	0.7880	0.5778	0.045*
C36	0.3934 (12)	0.7424 (3)	0.4678 (8)	0.027 (2)
H36	0.4151	0.7196	0.5154	0.032*
C41	0.3192 (13)	0.5837 (3)	0.4575 (7)	0.022 (2)
C42	0.4625 (13)	0.5922 (3)	0.5381 (7)	0.024 (2)
H42	0.4426	0.6128	0.5886	0.029*
C43	0.6336 (14)	0.5715 (3)	0.5465 (7)	0.024 (2)
C44	0.6650 (14)	0.5406 (3)	0.4736 (7)	0.025 (2)
C45	0.5206 (12)	0.5315 (3)	0.3945 (7)	0.023 (2)
H45	0.5392	0.5102	0.3456	0.027*
C46	0.3488 (13)	0.5527 (3)	0.3846 (8)	0.023 (2)
H46	0.2518	0.5463	0.3288	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
As1	0.0183 (5)	0.0151 (5)	0.0225 (6)	0.0018 (4)	0.0000 (4)	−0.0001 (4)
As2	0.0208 (5)	0.0148 (5)	0.0253 (6)	−0.0013 (4)	0.0022 (4)	−0.0004 (4)
As3	0.0167 (5)	0.0169 (5)	0.0281 (6)	0.0021 (4)	−0.0030 (4)	−0.0031 (5)
As4	0.0259 (5)	0.0211 (6)	0.0227 (6)	0.0022 (4)	0.0002 (4)	−0.0007 (4)
N1	0.016 (4)	0.027 (5)	0.029 (5)	−0.003 (4)	0.001 (4)	−0.001 (4)
N2	0.024 (5)	0.047 (6)	0.031 (6)	−0.019 (4)	−0.003 (4)	−0.001 (5)
N3	0.040 (6)	0.038 (6)	0.034 (6)	−0.010 (5)	−0.012 (5)	0.008 (5)
N4	0.037 (5)	0.032 (5)	0.029 (5)	−0.002 (4)	−0.007 (4)	0.009 (5)
O1	0.017 (3)	0.012 (3)	0.031 (4)	−0.002 (3)	0.005 (3)	0.002 (3)
O2	0.024 (3)	0.018 (3)	0.020 (4)	0.001 (3)	−0.006 (3)	−0.005 (3)
O3	0.026 (4)	0.016 (3)	0.023 (4)	0.004 (3)	0.001 (3)	−0.004 (3)
O4	0.023 (3)	0.014 (3)	0.020 (4)	0.003 (3)	−0.003 (3)	−0.002 (3)
O11	0.021 (3)	0.026 (4)	0.025 (4)	−0.002 (3)	0.000 (3)	0.005 (3)
O12	0.021 (3)	0.019 (4)	0.036 (4)	0.004 (3)	−0.003 (3)	0.013 (3)
O13	0.049 (5)	0.023 (4)	0.026 (4)	0.002 (3)	0.004 (4)	−0.002 (3)
O21	0.039 (4)	0.034 (4)	0.038 (5)	−0.002 (3)	−0.001 (4)	−0.019 (4)
O22	0.045 (5)	0.056 (5)	0.029 (5)	−0.015 (4)	0.008 (4)	−0.023 (4)
O23	0.066 (6)	0.046 (5)	0.031 (5)	−0.009 (4)	−0.010 (4)	0.008 (4)
O31	0.039 (4)	0.019 (4)	0.081 (6)	0.007 (4)	−0.005 (4)	−0.017 (4)
O32	0.087 (7)	0.041 (5)	0.041 (6)	−0.009 (5)	0.001 (5)	0.004 (4)
O33	0.067 (6)	0.013 (4)	0.073 (6)	−0.009 (4)	−0.005 (5)	−0.001 (4)
O41	0.026 (4)	0.035 (4)	0.037 (5)	0.009 (3)	−0.005 (3)	0.002 (4)
O42	0.052 (5)	0.041 (5)	0.025 (4)	−0.004 (4)	−0.002 (4)	−0.010 (4)
O43	0.035 (4)	0.049 (5)	0.043 (5)	0.011 (4)	−0.016 (4)	0.010 (4)
C11	0.017 (5)	0.025 (6)	0.016 (5)	−0.003 (4)	0.002 (4)	0.005 (4)
C12	0.016 (5)	0.028 (6)	0.015 (5)	−0.001 (4)	0.004 (4)	0.004 (4)
C13	0.019 (5)	0.010 (5)	0.022 (6)	0.000 (4)	0.007 (4)	−0.001 (4)
C14	0.012 (5)	0.034 (6)	0.016 (6)	−0.004 (4)	0.001 (4)	0.008 (4)
C15	0.017 (5)	0.029 (6)	0.019 (5)	−0.010 (4)	0.005 (4)	−0.007 (5)
C16	0.014 (5)	0.024 (6)	0.028 (6)	−0.001 (4)	0.004 (4)	−0.001 (5)
C21	0.018 (5)	0.018 (5)	0.019 (6)	−0.008 (4)	−0.001 (4)	−0.008 (4)
C22	0.008 (4)	0.024 (5)	0.033 (6)	−0.006 (4)	0.001 (4)	−0.005 (5)
C23	0.020 (5)	0.032 (6)	0.011 (5)	−0.005 (4)	−0.001 (4)	0.001 (4)
C24	0.016 (5)	0.031 (6)	0.035 (7)	−0.006 (4)	0.003 (5)	−0.012 (5)
C25	0.028 (6)	0.020 (5)	0.030 (6)	0.009 (4)	−0.005 (5)	−0.001 (5)
C26	0.025 (5)	0.024 (6)	0.023 (6)	0.001 (4)	−0.003 (4)	−0.007 (5)
C31	0.009 (5)	0.019 (5)	0.049 (7)	−0.003 (4)	0.005 (5)	−0.008 (5)
C32	0.010 (5)	0.026 (6)	0.048 (7)	−0.008 (4)	0.003 (5)	−0.008 (5)
C33	0.012 (5)	0.030 (6)	0.060 (8)	0.000 (4)	0.005 (5)	0.013 (6)
C34	0.014 (5)	0.050 (8)	0.034 (7)	−0.003 (5)	0.004 (5)	0.000 (6)
C35	0.015 (5)	0.055 (8)	0.046 (8)	−0.003 (5)	0.013 (5)	−0.003 (6)
C36	0.013 (5)	0.027 (6)	0.041 (7)	−0.001 (4)	0.003 (5)	−0.010 (5)
C41	0.030 (6)	0.016 (5)	0.020 (5)	0.004 (4)	−0.003 (4)	0.006 (4)
C42	0.029 (6)	0.019 (5)	0.025 (6)	0.006 (4)	0.004 (5)	0.006 (4)
C43	0.030 (6)	0.022 (6)	0.017 (5)	−0.008 (4)	−0.003 (5)	0.003 (4)
C44	0.037 (6)	0.021 (6)	0.018 (6)	0.005 (5)	0.002 (5)	0.009 (4)
C45	0.023 (5)	0.022 (5)	0.021 (6)	−0.002 (4)	−0.002 (4)	−0.001 (4)
C46	0.023 (5)	0.021 (5)	0.025 (6)	−0.004 (4)	−0.001 (4)	0.006 (5)

Geometric parameters (Å, º) top

As1—O4	1.789 (6)	C12—C13	1.403 (12)
As1—O1	1.811 (6)	C12—H12	0.9500
As1—C11	1.934 (9)	C13—C14	1.377 (12)
As2—O1	1.790 (6)	C14—C15	1.371 (13)
As2—O2	1.807 (6)	C15—C16	1.391 (12)
As2—C21	1.962 (9)	C15—H15	0.9500
As3—O3	1.799 (6)	C16—H16	0.9500
As3—O4	1.816 (6)	C21—C22	1.357 (12)
As3—C31	1.948 (9)	C21—C26	1.411 (12)
As4—O3	1.799 (6)	C22—C23	1.411 (12)
As4—O2	1.800 (6)	C22—H22	0.9500
As4—C41	1.966 (9)	C23—C24	1.402 (13)
N1—O13	1.216 (9)	C24—C25	1.387 (13)
N1—O12	1.247 (9)	C25—C26	1.376 (12)
N1—C13	1.461 (11)	C25—H25	0.9500
N2—O23	1.219 (10)	C26—H26	0.9500
N2—O22	1.243 (10)	C31—C32	1.365 (13)
N2—C23	1.457 (12)	C31—C36	1.391 (13)
N3—O32	1.229 (11)	C32—C33	1.441 (14)
N3—O33	1.262 (10)	C32—H32	0.9500
N3—C33	1.412 (13)	C33—C34	1.396 (14)
N4—O42	1.227 (10)	C34—C35	1.367 (14)
N4—O43	1.242 (10)	C35—C36	1.383 (14)
N4—C43	1.463 (12)	C35—H35	0.9500
O11—C14	1.367 (10)	C36—H36	0.9500
O11—H11	0.8400	C41—C42	1.382 (12)
O21—C24	1.349 (11)	C41—C46	1.402 (13)
O21—H21	0.8400	C42—C43	1.376 (13)
O31—C34	1.370 (12)	C42—H42	0.9500
O31—H31	0.8400	C43—C44	1.402 (13)
O41—C44	1.367 (11)	C44—C45	1.378 (12)
O41—H41	0.8400	C45—C46	1.387 (12)
C11—C12	1.391 (12)	C45—H45	0.9500
C11—C16	1.405 (12)	C46—H46	0.9500

O4—As1—O1	95.8 (3)	C26—C21—As2	118.9 (7)
O4—As1—C11	94.5 (3)	C21—C22—C23	119.7 (9)
O1—As1—C11	94.0 (3)	C21—C22—H22	120.1
O1—As2—O2	98.8 (3)	C23—C22—H22	120.1
O1—As2—C21	98.4 (3)	C24—C23—C22	121.8 (9)
O2—As2—C21	91.4 (3)	C24—C23—N2	120.5 (9)
O3—As3—O4	101.0 (3)	C22—C23—N2	117.7 (9)
O3—As3—C31	90.2 (4)	O21—C24—C25	116.2 (9)
O4—As3—C31	94.0 (3)	O21—C24—C23	126.2 (9)
O3—As4—O2	99.6 (3)	C25—C24—C23	117.5 (9)
O3—As4—C41	98.4 (3)	C26—C25—C24	120.5 (9)
O2—As4—C41	92.8 (3)	C26—C25—H25	119.7
O13—N1—O12	122.3 (8)	C24—C25—H25	119.7
O13—N1—C13	119.7 (8)	C25—C26—C21	121.8 (9)
O12—N1—C13	118.0 (8)	C25—C26—H26	119.1
O23—N2—O22	123.0 (9)	C21—C26—H26	119.1
O23—N2—C23	119.9 (9)	C32—C31—C36	118.5 (9)
O22—N2—C23	117.1 (9)	C32—C31—As3	121.3 (8)
O32—N3—O33	121.7 (9)	C36—C31—As3	120.2 (8)
O32—N3—C33	121.3 (9)	C31—C32—C33	119.2 (10)
O33—N3—C33	117.0 (9)	C31—C32—H32	120.4
O42—N4—O43	124.0 (9)	C33—C32—H32	120.4
O42—N4—C43	118.7 (8)	C34—C33—N3	124.0 (10)
O43—N4—C43	117.2 (9)	C34—C33—C32	119.9 (10)
As2—O1—As1	119.3 (3)	N3—C33—C32	116.1 (10)
As4—O2—As2	123.8 (3)	C35—C34—O31	117.0 (10)
As3—O3—As4	123.1 (3)	C35—C34—C33	120.5 (10)
As1—O4—As3	118.8 (3)	O31—C34—C33	122.4 (10)
C14—O11—H11	109.5	C34—C35—C36	118.3 (11)
C24—O21—H21	109.5	C34—C35—H35	120.8
C34—O31—H31	109.5	C36—C35—H35	120.8
C44—O41—H41	109.5	C35—C36—C31	123.6 (10)
C12—C11—C16	118.5 (8)	C35—C36—H36	118.2
C12—C11—As1	121.5 (7)	C31—C36—H36	118.2
C16—C11—As1	120.0 (7)	C42—C41—C46	119.0 (9)
C11—C12—C13	118.9 (8)	C42—C41—As4	119.4 (7)
C11—C12—H12	120.5	C46—C41—As4	121.6 (7)
C13—C12—H12	120.5	C43—C42—C41	121.1 (9)
C14—C13—C12	122.3 (8)	C43—C42—H42	119.5
C14—C13—N1	121.9 (8)	C41—C42—H42	119.5
C12—C13—N1	115.8 (8)	C42—C43—C44	120.4 (9)
O11—C14—C15	116.1 (8)	C42—C43—N4	118.1 (9)
O11—C14—C13	125.4 (9)	C44—C43—N4	121.5 (9)
C15—C14—C13	118.5 (9)	O41—C44—C45	117.7 (9)
C14—C15—C16	120.8 (9)	O41—C44—C43	123.7 (9)
C14—C15—H15	119.6	C45—C44—C43	118.5 (9)
C16—C15—H15	119.6	C44—C45—C46	121.5 (9)
C15—C16—C11	120.8 (9)	C44—C45—H45	119.3
C15—C16—H16	119.6	C46—C45—H45	119.3
C11—C16—H16	119.6	C45—C46—C41	119.6 (9)
C22—C21—C26	118.7 (8)	C45—C46—H46	120.2
C22—C21—As2	122.1 (7)	C41—C46—H46	120.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11···O12	0.84	1.91	2.614 (9)	140
O21—H21···O22	0.84	1.88	2.579 (11)	141
O31—H31···O33	0.84	1.86	2.572 (11)	142
O41—H41···O43	0.84	1.86	2.569 (10)	142
O11—H11···O1ⁱ	0.84	2.65	3.260 (8)	131
C15—H15···O42ⁱⁱ	0.95	2.47	3.191 (12)	132
C25—H25···O43ⁱⁱⁱ	0.95	2.47	3.151 (12)	128
C15—H15···O13ⁱ	0.95	2.70	3.539 (12)	148
C12—H12···O11^iv	0.95	2.61	3.340 (11)	134
C42—H42···O32^iv	0.95	2.48	3.355 (13)	154

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x−1, y, z−1; (iii) −x+1, −y+1, −z+1; (iv) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[As₄O₄(C₆H₄NO₃)₄]
M_r	916.09
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	93
a, b, c (Å)	7.1289 (2), 31.6743 (9), 13.0217 (4)
β (°)	98.286 (1)
V (Å³)	2909.64 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.64
Crystal size (mm)	0.16 × 0.10 × 0.05

Data collection
Diffractometer	Siemens SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.524, 0.801
No. of measured, independent and observed [I > 2σ(I)] reflections	16032, 5490, 3294
R_int	0.114
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.131, 1.08
No. of reflections	5490
No. of parameters	433
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.03, −0.91

Computer programs: SMART (Bruker 2001), SAINT (Bruker 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11···O12	0.84	1.91	2.614 (9)	140.1
O21—H21···O22	0.84	1.88	2.579 (11)	140.5
O31—H31···O33	0.84	1.86	2.572 (11)	141.8
O41—H41···O43	0.84	1.86	2.569 (10)	141.6
O11—H11···O1ⁱ	0.84	2.65	3.260 (8)	131.2
C15—H15···O42ⁱⁱ	0.95	2.47	3.191 (12)	132.3
C25—H25···O43ⁱⁱⁱ	0.95	2.47	3.151 (12)	128.3
C15—H15···O13ⁱ	0.95	2.70	3.539 (12)	147.6
C12—H12···O11^iv	0.95	2.61	3.340 (11)	133.8
C42—H42···O32^iv	0.95	2.48	3.355 (13)	153.9

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x−1, y, z−1; (iii) −x+1, −y+1, −z+1; (iv) x, −y+3/2, z+1/2.

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page