Triethyl­ammonium bis­(2-oxido-2,2-diphenyl­acetato-κ2O1,O2)anti­monate(III)

Reza, Md.Y.; Hossain, Md.M.; Karim, Md.R.; Tarafder, Md.T.H.; Hughes, D.L.

doi:10.1107/S1600536809054853

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 2| February 2010| Pages m116-m117

https://doi.org/10.1107/S1600536809054853

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Triethylammonium bis(2-oxido-2,2-diphenylacetato-κ²O¹,O²)antimonate(III)

Md. Yeamin Reza,^a Md. Motahar Hossain,^a ^*‡ Md. Rabiul Karim,^a Md. Tofazzal Hossain Tarafder ^a and David L. Hughes ^b

^aDepartment of Chemistry, University of Rajshahi, Rajshahi 6205, Bangladesh, and ^bSchool of Chemistry, University of East Anglia, Norwich NR4 7TJ, England
^*Correspondence e-mail: motahar_chem@ru.ac.bd

(Received 21 November 2009; accepted 21 December 2009; online 9 January 2010)

The coordination around the Sb atom in the title compound, (C₆H₁₆N)[Sb(C₁₄H₁₀O₃)₂], is fourfold in a pseudo-trigonal-bipyramidal pattern in which one of the equatorial sites is occupied by the stereoactive lone pair of electrons. The four ligating atoms comprise the hydoxylate and carboxylate O atoms from two independent benzilate ligands, each of which forms a five-membered chelating ring, spanning an axial and an equatorial site about the Sb atom. The hydroxylate atoms occupy the two equatorial sites, and the carboxylate atoms are in the pseudo-axial sites; the O—Sb—O angle is 147.72 (5)°. One carboxylate group shows quite different bond lengths from those of the other group; one O atom is clearly the carbonyl atom and the other O atom the hydroxylate atom. In the other ligand, there is less distinction in the C—O bonds. This is presumably related to the carbonyl O atom being the acceptor atom of a strong N—H⋯O hydrogen bond, which links the ammonium cation to the Sb complex anion.

Related literature

For metal–carboxylate and alkoxide complexes: Reza et al. (1998 , 1999 , 2003 ); Tarafder et al. (2008 ). For antimony(III) complexes, see: Razak et al. (2002 ); Vijjulatha et al. (1997 ). For α-hydroxycarboxylate complexes, see: Hartley et al. (1991 ); Smith et al. (1992 , 1993 ); Smith & Kennard (1996 ); Bott et al. (2000 ); Redshaw & Elsegood (2007 ); Redshaw et al. (2005 ); Chandrasekhar et al. (2005 ); Vergopoulos et al. (1995 ); Carballo et al. (2004a ,b ).

Experimental

Crystal data

(C₆H₁₆N)[Sb(C₁₄H₁₀O₃)₂]
M_r = 676.39
Monoclinic, P 2₁ /c
a = 12.34379 (13) Å
b = 10.63317 (12) Å
c = 22.5264 (3) Å
β = 90.6466 (11)°
V = 2956.49 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.98 mm⁻¹
T = 140 K
0.28 × 0.27 × 0.09 mm

Data collection

Oxford Diffraction Xcalibur 3/CCD diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.911, T_max = 1.000
61564 measured reflections
6772 independent reflections
5645 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.049
S = 1.01
6772 reflections
383 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Sb—O1	2.2091 (12)
Sb—O2	1.9751 (11)
Sb—O4	2.1204 (12)
Sb—O5	1.9662 (11)

O2—Sb—O1	76.77 (4)
O4—Sb—O1	147.72 (5)
O5—Sb—O1	81.60 (5)
O2—Sb—O4	81.84 (5)
O5—Sb—O2	100.79 (5)
O5—Sb—O4	78.97 (5)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7⋯O11	0.93 (2)	1.78 (2)	2.706 (2)	177.5 (18)

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976 ) and ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809054853/pb2016sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809054853/pb2016Isup2.hkl

checkCIF report

Comment top

In an ongoing study of metal-carboxylate and -alkoxide complexes (Reza et al., 1998, 1999, 2003; Tarafder et al., 2008), with particular interest in their antimicrobial and catalytic properties, we are exploring the coordination chemistry of some α-hydroxycarboxylate ions which contain both the ligating groups of interest and whose parent acids have important roles in enzyme reactions. Often, the α-hydroxycarboxylate ligand forms a simple chelating ring with a metal (e.g. Vergopoulos et al., 1995), but terminal and bridging modes have also been found (e.g. Carballo et al., 2004a, 2004b). The bridging modes, using the three (or more) available oxygen donor atoms, allow the formation of oligomeric complexes, for example the macrocyclic rings formed between benzilate ions and AlMe₃ (Redshaw et al., 2005) or ZnEt₂ (Redshaw et al., 2007), and the cages formed by 9-hydroxy-9-fluorenecarboxylic acid with n-BuSn(O)OH (Chandrasekhar et al., 2005). We recall also the series of citrate complexes in which the citrate ion chelates an antimony ion and bridges to a range of simple cations (alkali metals, copper, silver, etc) to form a variety of polymeric structures (Hartley et al., 1991, Smith et al., 1992, 1993, Bott et al., 2000).

We have now prepared an Sb(III) complex of the benzilate (diphenylglycolate) ion, with Et₃NH⁺ as the counterion. This cation is non-coordinating and has a single N-H group with potential for formation of hydrogen bonds. The product, the title compound (I), shows (Figure 1) the antimony atom coordinated by two independent benzilate ligands with very similar conformations, each with a five-membered chelating ring which bridges an axial and equatorial site of the pseudo trigonal bipyramidal coordination polyhedron; the fifth, equatorial coordination site is occupied by a stereoactive lone-pair of electrons in the style typical of antimony(III) complexes of citrate and other α-hydrocarboxylate ions. In all these Sb(III) complexes, the alkoxide O atom is in an equatorial position and one of the carboxylate O atoms is in an axial site, and the axial Sb—O bonds are slightly longer than the equatorial bonds. Slight differences in the dimensions of the carboxylate groups in our complex are thought to result from the participation of one of these groups as acceptor of a good, almost linear hydrogen bond, N(7)—H(7)···O(11), from the Et₃NH⁺ cation. The Sb(OOCCOPh₂)₂^- anion and Et₃NH⁺ cation thus appear as a discrete ion-pair unit in the crystal.

On the Sb atom, the lone-pair of electrons (and vacant coordination site) are bounded by the phenyl group of C(51¹-56¹) and O(41¹) of the molecule at (1 - x, y - 1/2, 1/2 - z), Figure 2; a point X calculated along the bisecting vectors towards the coordination site, at 1.5 Å from the Sb atom, has X···C distances in the range 2.45 - 2.90 Å and X···O(41¹) 2.70 Å.

There are two intermolecular 'weak hydrogen bonds', viz C(24)—H(24)···O(2²) and C(75)—H(75b)···O(41³) with H···O contacts of 2.44 and 2.49 Å. The other major intermolecular contacts are C—H···π interactions, e.g. the phenyl group of C(21–26) is bounded on one side by the hydrogen atom H(54¹), and on the other side H(73b⁴) where these hydrogen atoms are displaced 2.95 and 2.61 Å from the ring mean-plane. The ring of C(31–36) has a similar interaction, with H(74b) displaced 2.73 Å from the ring plane, but on the opposite side, H(54⁵) is directed at the C(35)—C(36) bond. As noted above, the ring of C(51–56) has a lone-pair of electrons on one side; H(76a⁶) is on the opposite side but points more to the C(51) end of the ring. The hydrogen atoms H(35 and 36) and H(72a⁷), approaching the ring of C(61–66), are also directed at the edges of the ring. [Symmetry operations, denoted by superscripts are: 1: 1 - x, y - 1/2, 1/2 - z; 2: -x, y - 1/2, 1/2 - z; 3: x, 3/2 - y, 1/2 + z; 4: -x, 1 - y, 1 - z; 5: x - 1, y, z; 6: 1 - x, 1 - y, 1 - z; 7: 1 - x, 2 - y, 1 - z].

Molecular dimensions are available in the archived CIF.

Related literature top

For metal–carboxylate and alkoxide complexes: Reza et al. (1998, 1999, 2003); Tarafder et al. (2008). For antimony(III) complexes, see: Razak et al. (2002); Vijjulatha et al. (1997). For α-hydroxycarboxylate complexes, see: Hartley et al. (1991); Smith et al. (1992, 1993); Smith & Kennard (1996); Bott et al. (2000); Redshaw & Elsegood (2007); Redshaw et al. (2005); Chandrasekhar et al. (2005); Vergopoulos et al. (1995); Carballo et al. (2004a,b).

Experimental top

The title complex, (Et₃NH) [Sb(Ph₂COCOO)₂] (1) was synthesized by adding, with stirring, a mixture of benzilic acid (2 mmol) and triethylamine (2 mmol) in acetonitrile (50 ml) to 30 ml of an aqueous solution of SbCl₃ (1 mmol). The stirring was continued for another 30 min at 60 C. Precipitates initially formed were filtered and the filtrate was concentrated to one-third of its original volume (ca 30 ml). The colourless single crystals of 1 which appeared after a week were collected, washed with water and dried in air at room temperature, Mp. 558 K.

Structure description top

Molecular dimensions are available in the archived CIF.

For metal–carboxylate and alkoxide complexes: Reza et al. (1998, 1999, 2003); Tarafder et al. (2008). For antimony(III) complexes, see: Razak et al. (2002); Vijjulatha et al. (1997). For α-hydroxycarboxylate complexes, see: Hartley et al. (1991); Smith et al. (1992, 1993); Smith & Kennard (1996); Bott et al. (2000); Redshaw & Elsegood (2007); Redshaw et al. (2005); Chandrasekhar et al. (2005); Vergopoulos et al. (1995); Carballo et al. (2004a,b).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. View of a molecule of (Et₃NH)[Sb(Ph₂COCOO)₂] (1), indicating the atom numbering scheme. Hydrogen atoms (except that involved in the hydrogen bond) have been omitted for clarity. Thermal ellipsoids are drawn at the 30% probability level.
	Fig. 2. Environs of lone-pair of electrons (around the point X) of the antimony atom. The superscript denotes the symmetry operation: 1 - x, y - 1/2, 1/2 - z.

Triethylammonium bis(2-oxido-2,2-diphenylacetato-κ²O¹,O²)antimonate(III) top

Crystal data top

(C₆H₁₆N)[Sb(C₁₄H₁₀O₃)₂]	F(000) = 1384
M_r = 676.39	D_x = 1.520 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.34379 (13) Å	Cell parameters from 33278 reflections
b = 10.63317 (12) Å	θ = 3.1–32.3°
c = 22.5264 (3) Å	µ = 0.98 mm⁻¹
β = 90.6466 (11)°	T = 140 K
V = 2956.49 (5) Å³	Plate, colourless
Z = 4	0.28 × 0.27 × 0.09 mm

Data collection top

Oxford Diffraction Xcalibur 3/CCD diffractometer	6772 independent reflections
Radiation source: Enhance (Mo) X-ray Source	5645 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
Detector resolution: 16.0050 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
Thin–slice φ and ω scans	h = −16→16
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −13→13
T_min = 0.911, T_max = 1.000	l = −29→29
61564 measured reflections

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.049	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0274P)²] where P = (F_o² + 2F_c²)/3
6772 reflections	(Δ/σ)_max = 0.003
383 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

(C₆H₁₆N)[Sb(C₁₄H₁₀O₃)₂]	V = 2956.49 (5) Å³
M_r = 676.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.34379 (13) Å	µ = 0.98 mm⁻¹
b = 10.63317 (12) Å	T = 140 K
c = 22.5264 (3) Å	0.28 × 0.27 × 0.09 mm
β = 90.6466 (11)°

Data collection top

Oxford Diffraction Xcalibur 3/CCD diffractometer	6772 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	5645 reflections with I > 2σ(I)
T_min = 0.911, T_max = 1.000	R_int = 0.054
61564 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	0 restraints
wR(F²) = 0.049	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.41 e Å⁻³
6772 reflections	Δρ_min = −0.42 e Å⁻³
383 parameters

Special details top

Experimental. CrysAlisPro RED, Oxford Diffraction Ltd., Version 1.171.32.24 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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) top

	x	y	z	U_iso*/U_eq
Sb	0.344289 (9)	0.578178 (10)	0.306991 (5)	0.01409 (4)
O1	0.31229 (9)	0.51859 (11)	0.39909 (6)	0.0186 (3)
C1	0.21403 (13)	0.53115 (16)	0.41481 (8)	0.0146 (3)
O11	0.17823 (10)	0.49894 (12)	0.46352 (5)	0.0199 (3)
C2	0.13642 (13)	0.58983 (15)	0.36784 (7)	0.0125 (3)
O2	0.19745 (9)	0.64426 (11)	0.32163 (5)	0.0144 (2)
C21	0.06322 (13)	0.48800 (16)	0.34061 (8)	0.0137 (3)
C22	0.07864 (14)	0.36064 (17)	0.35079 (8)	0.0187 (4)
H22	0.1310	0.3342	0.3781	0.022*
C23	0.01619 (15)	0.27202 (17)	0.32035 (8)	0.0225 (4)
H23	0.0279	0.1867	0.3270	0.027*
C24	−0.06292 (14)	0.30980 (18)	0.28049 (8)	0.0231 (4)
H24	−0.1044	0.2505	0.2601	0.028*
C25	−0.07987 (14)	0.43711 (18)	0.27118 (8)	0.0226 (4)
H25	−0.1336	0.4634	0.2447	0.027*
C26	−0.01765 (14)	0.52544 (17)	0.30094 (8)	0.0178 (4)
H26	−0.0300	0.6106	0.2944	0.021*
C31	0.06915 (13)	0.69218 (15)	0.39781 (8)	0.0142 (3)
C32	−0.01336 (14)	0.65910 (17)	0.43647 (8)	0.0184 (4)
H32	−0.0279	0.5746	0.4436	0.022*
C33	−0.07398 (14)	0.75074 (18)	0.46439 (9)	0.0229 (4)
H33	−0.1288	0.7277	0.4902	0.027*
C34	−0.05292 (15)	0.87695 (18)	0.45388 (9)	0.0243 (4)
H34	−0.0941	0.9388	0.4721	0.029*
C35	0.02932 (16)	0.90969 (17)	0.41627 (9)	0.0242 (4)
H35	0.0440	0.9942	0.4095	0.029*
C36	0.09080 (14)	0.81839 (16)	0.38823 (8)	0.0194 (4)
H36	0.1464	0.8419	0.3630	0.023*
O4	0.34473 (9)	0.72582 (12)	0.24372 (5)	0.0201 (3)
C4	0.39510 (14)	0.82763 (17)	0.25927 (8)	0.0195 (4)
O41	0.40424 (11)	0.91988 (13)	0.22763 (6)	0.0311 (3)
C5	0.44681 (13)	0.82505 (16)	0.32260 (8)	0.0153 (3)
O5	0.43343 (9)	0.70446 (10)	0.34853 (5)	0.0166 (3)
C51	0.56859 (13)	0.84740 (16)	0.31541 (8)	0.0147 (3)
C52	0.62838 (14)	0.75725 (17)	0.28514 (9)	0.0220 (4)
H52	0.5933	0.6876	0.2689	0.026*
C53	0.73872 (15)	0.76966 (18)	0.27882 (9)	0.0264 (4)
H53	0.7774	0.7085	0.2585	0.032*
C54	0.79229 (15)	0.87246 (19)	0.30243 (9)	0.0259 (4)
H54	0.8669	0.8803	0.2986	0.031*
C55	0.73385 (15)	0.96320 (19)	0.33175 (9)	0.0249 (4)
H55	0.7693	1.0330	0.3475	0.030*
C56	0.62251 (14)	0.95149 (16)	0.33797 (8)	0.0197 (4)
H56	0.5839	1.0140	0.3574	0.024*
C61	0.39459 (13)	0.92205 (17)	0.36336 (9)	0.0210 (4)
C62	0.33837 (16)	1.0251 (2)	0.34307 (11)	0.0354 (5)
H62	0.3300	1.0384	0.3025	0.043*
C63	0.2942 (2)	1.1093 (2)	0.38288 (15)	0.0536 (8)
H63	0.2562	1.1787	0.3687	0.064*
C64	0.30550 (18)	1.0921 (2)	0.44250 (14)	0.0515 (8)
H64	0.2745	1.1487	0.4688	0.062*
C65	0.3631 (2)	0.9904 (2)	0.46345 (12)	0.0501 (7)
H65	0.3726	0.9787	0.5041	0.060*
C66	0.40684 (19)	0.9058 (2)	0.42384 (10)	0.0377 (5)
H66	0.4452	0.8367	0.4382	0.045*
N7	0.28608 (12)	0.57191 (14)	0.56292 (7)	0.0187 (3)
C71	0.38735 (15)	0.6338 (2)	0.54177 (10)	0.0293 (5)
H71A	0.3677	0.7009	0.5145	0.035*
H71B	0.4295	0.5727	0.5199	0.035*
C72	0.45699 (17)	0.6876 (2)	0.59098 (11)	0.0404 (6)
H72A	0.5203	0.7258	0.5744	0.061*
H72B	0.4785	0.6215	0.6176	0.061*
H72C	0.4166	0.7498	0.6123	0.061*
C73	0.21227 (15)	0.65915 (17)	0.59532 (8)	0.0217 (4)
H73A	0.2481	0.6871	0.6315	0.026*
H73B	0.1474	0.6137	0.6064	0.026*
C74	0.18027 (17)	0.77240 (19)	0.55908 (9)	0.0316 (5)
H74A	0.1336	0.8253	0.5820	0.047*
H74B	0.1428	0.7456	0.5237	0.047*
H74C	0.2440	0.8185	0.5484	0.047*
C75	0.30507 (16)	0.45419 (17)	0.59820 (8)	0.0234 (4)
H75A	0.2360	0.4205	0.6107	0.028*
H75B	0.3472	0.4743	0.6335	0.028*
C76	0.36437 (17)	0.35545 (19)	0.56253 (9)	0.0313 (5)
H76A	0.3595	0.2757	0.5823	0.047*
H76B	0.4391	0.3789	0.5590	0.047*
H76C	0.3321	0.3492	0.5237	0.047*
H7	0.2489 (16)	0.5445 (18)	0.5292 (9)	0.021 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sb	0.01236 (6)	0.01524 (6)	0.01468 (6)	0.00074 (5)	0.00095 (4)	−0.00073 (5)
O1	0.0142 (6)	0.0211 (6)	0.0203 (7)	0.0006 (5)	−0.0024 (5)	0.0061 (5)
C1	0.0163 (8)	0.0120 (8)	0.0155 (9)	−0.0021 (6)	−0.0032 (7)	0.0003 (7)
O11	0.0208 (6)	0.0252 (7)	0.0137 (7)	−0.0039 (5)	−0.0014 (5)	0.0044 (5)
C2	0.0122 (7)	0.0143 (8)	0.0111 (8)	−0.0004 (6)	0.0001 (6)	0.0017 (7)
O2	0.0104 (5)	0.0199 (6)	0.0128 (6)	0.0004 (5)	0.0016 (5)	0.0050 (5)
C21	0.0116 (8)	0.0173 (9)	0.0122 (8)	−0.0007 (6)	0.0028 (7)	−0.0031 (7)
C22	0.0165 (9)	0.0201 (9)	0.0196 (10)	0.0017 (7)	−0.0009 (7)	−0.0030 (7)
C23	0.0234 (9)	0.0167 (9)	0.0276 (11)	−0.0008 (7)	0.0035 (8)	−0.0064 (8)
C24	0.0186 (9)	0.0298 (11)	0.0211 (10)	−0.0059 (8)	0.0026 (8)	−0.0116 (8)
C25	0.0169 (9)	0.0321 (11)	0.0186 (9)	0.0000 (8)	−0.0040 (7)	−0.0032 (8)
C26	0.0172 (9)	0.0198 (9)	0.0162 (9)	−0.0003 (7)	−0.0013 (7)	−0.0009 (7)
C31	0.0128 (8)	0.0176 (9)	0.0122 (8)	0.0002 (6)	−0.0034 (7)	−0.0017 (7)
C32	0.0169 (9)	0.0177 (9)	0.0208 (10)	−0.0029 (7)	0.0011 (7)	−0.0017 (7)
C33	0.0174 (9)	0.0273 (10)	0.0240 (10)	−0.0012 (8)	0.0046 (8)	−0.0047 (8)
C34	0.0238 (10)	0.0230 (9)	0.0262 (11)	0.0064 (8)	−0.0002 (8)	−0.0079 (8)
C35	0.0302 (10)	0.0151 (9)	0.0274 (10)	0.0010 (8)	−0.0007 (8)	−0.0015 (8)
C36	0.0202 (9)	0.0204 (9)	0.0177 (9)	−0.0018 (7)	0.0004 (7)	0.0015 (7)
O4	0.0179 (6)	0.0271 (7)	0.0153 (6)	−0.0026 (5)	−0.0013 (5)	0.0032 (5)
C4	0.0139 (8)	0.0259 (10)	0.0189 (10)	0.0035 (7)	0.0018 (7)	0.0057 (8)
O41	0.0336 (8)	0.0303 (8)	0.0292 (8)	−0.0038 (6)	−0.0051 (6)	0.0166 (7)
C5	0.0144 (8)	0.0150 (8)	0.0165 (9)	−0.0006 (6)	0.0009 (7)	0.0044 (7)
O5	0.0166 (6)	0.0161 (6)	0.0170 (6)	−0.0037 (5)	−0.0039 (5)	0.0051 (5)
C51	0.0139 (8)	0.0151 (8)	0.0152 (9)	−0.0004 (6)	0.0004 (7)	0.0049 (7)
C52	0.0203 (9)	0.0176 (9)	0.0283 (11)	−0.0007 (7)	0.0037 (8)	−0.0027 (8)
C53	0.0209 (9)	0.0258 (10)	0.0328 (12)	0.0045 (8)	0.0084 (8)	−0.0029 (9)
C54	0.0137 (9)	0.0353 (11)	0.0287 (11)	−0.0021 (8)	0.0006 (8)	0.0035 (9)
C55	0.0195 (9)	0.0303 (10)	0.0249 (11)	−0.0091 (8)	−0.0015 (8)	−0.0027 (8)
C56	0.0210 (9)	0.0200 (10)	0.0181 (9)	−0.0003 (7)	0.0018 (7)	−0.0021 (7)
C61	0.0129 (8)	0.0200 (9)	0.0303 (10)	−0.0037 (7)	0.0068 (7)	−0.0011 (8)
C62	0.0278 (11)	0.0266 (11)	0.0516 (15)	0.0058 (9)	−0.0084 (10)	−0.0058 (11)
C63	0.0339 (13)	0.0348 (14)	0.092 (2)	0.0164 (10)	−0.0059 (14)	−0.0206 (14)
C64	0.0288 (12)	0.0404 (15)	0.086 (2)	−0.0080 (10)	0.0289 (13)	−0.0346 (15)
C65	0.0664 (18)	0.0438 (15)	0.0409 (15)	−0.0146 (13)	0.0332 (14)	−0.0149 (12)
C66	0.0536 (14)	0.0298 (12)	0.0301 (12)	0.0052 (10)	0.0191 (11)	0.0008 (9)
N7	0.0203 (7)	0.0211 (8)	0.0148 (7)	−0.0020 (6)	−0.0002 (6)	−0.0011 (7)
C71	0.0267 (10)	0.0290 (11)	0.0326 (12)	−0.0049 (9)	0.0121 (9)	−0.0002 (9)
C72	0.0242 (11)	0.0432 (14)	0.0539 (16)	−0.0119 (10)	0.0011 (11)	−0.0037 (11)
C73	0.0206 (9)	0.0249 (10)	0.0199 (10)	−0.0008 (7)	0.0036 (8)	−0.0047 (8)
C74	0.0366 (12)	0.0265 (11)	0.0315 (12)	0.0037 (9)	−0.0042 (10)	−0.0043 (9)
C75	0.0289 (10)	0.0254 (10)	0.0157 (9)	−0.0017 (8)	−0.0054 (8)	0.0034 (7)
C76	0.0382 (12)	0.0299 (12)	0.0255 (11)	0.0100 (9)	−0.0098 (9)	−0.0004 (9)

Geometric parameters (Å, º) top

Sb—O1	2.2091 (12)	C52—H52	0.9300
Sb—O2	1.9751 (11)	C53—C54	1.381 (3)
Sb—O4	2.1204 (12)	C53—H53	0.9300
Sb—O5	1.9662 (11)	C54—C55	1.378 (3)
O1—C1	1.274 (2)	C54—H54	0.9300
C1—O11	1.236 (2)	C55—C56	1.389 (2)
C1—C2	1.550 (2)	C55—H55	0.9300
C2—O2	1.4155 (19)	C56—H56	0.9300
C2—C31	1.530 (2)	C61—C62	1.373 (3)
C2—C21	1.534 (2)	C61—C66	1.380 (3)
C21—C22	1.386 (2)	C62—C63	1.383 (3)
C21—C26	1.390 (2)	C62—H62	0.9300
C22—C23	1.393 (2)	C63—C64	1.361 (4)
C22—H22	0.9300	C63—H63	0.9300
C23—C24	1.379 (3)	C64—C65	1.375 (4)
C23—H23	0.9300	C64—H64	0.9300
C24—C25	1.385 (3)	C65—C66	1.382 (3)
C24—H24	0.9300	C65—H65	0.9300
C25—C26	1.382 (2)	C66—H66	0.9300
C25—H25	0.9300	N7—C71	1.495 (2)
C26—H26	0.9300	N7—C73	1.496 (2)
C31—C36	1.386 (2)	N7—C75	1.500 (2)
C31—C32	1.393 (2)	N7—H7	0.93 (2)
C32—C33	1.384 (2)	C71—C72	1.508 (3)
C32—H32	0.9300	C71—H71A	0.9700
C33—C34	1.388 (3)	C71—H71B	0.9700
C33—H33	0.9300	C72—H72A	0.9600
C34—C35	1.374 (3)	C72—H72B	0.9600
C34—H34	0.9300	C72—H72C	0.9600
C35—C36	1.389 (3)	C73—C74	1.505 (3)
C35—H35	0.9300	C73—H73A	0.9700
C36—H36	0.9300	C73—H73B	0.9700
O4—C4	1.295 (2)	C74—H74A	0.9600
C4—O41	1.218 (2)	C74—H74B	0.9600
C4—C5	1.557 (2)	C74—H74C	0.9600
C5—O5	1.4195 (19)	C75—C76	1.516 (3)
C5—C61	1.528 (2)	C75—H75A	0.9700
C5—C51	1.532 (2)	C75—H75B	0.9700
C51—C56	1.385 (2)	C76—H76A	0.9600
C51—C52	1.393 (2)	C76—H76B	0.9600
C52—C53	1.377 (2)	C76—H76C	0.9600

O2—Sb—O1	76.77 (4)	C52—C53—H53	119.8
O4—Sb—O1	147.72 (5)	C54—C53—H53	119.8
O5—Sb—O1	81.60 (5)	C55—C54—C53	119.20 (17)
O2—Sb—O4	81.84 (5)	C55—C54—H54	120.4
O5—Sb—O2	100.79 (5)	C53—C54—H54	120.4
O5—Sb—O4	78.97 (5)	C54—C55—C56	120.64 (18)
C1—O1—Sb	114.31 (11)	C54—C55—H55	119.7
O11—C1—O1	124.65 (16)	C56—C55—H55	119.7
O11—C1—C2	119.54 (15)	C51—C56—C55	120.44 (17)
O1—C1—C2	115.80 (14)	C51—C56—H56	119.8
O2—C2—C31	109.24 (13)	C55—C56—H56	119.8
O2—C2—C21	108.10 (13)	C62—C61—C66	118.57 (19)
C31—C2—C21	111.00 (13)	C62—C61—C5	123.62 (18)
O2—C2—C1	109.66 (12)	C66—C61—C5	117.80 (17)
C31—C2—C1	108.62 (13)	C61—C62—C63	120.1 (2)
C21—C2—C1	110.21 (13)	C61—C62—H62	119.9
C2—O2—Sb	118.32 (9)	C63—C62—H62	119.9
C22—C21—C26	118.83 (16)	C64—C63—C62	121.1 (2)
C22—C21—C2	122.98 (15)	C64—C63—H63	119.5
C26—C21—C2	118.05 (15)	C62—C63—H63	119.5
C21—C22—C23	120.35 (17)	C63—C64—C65	119.4 (2)
C21—C22—H22	119.8	C63—C64—H64	120.3
C23—C22—H22	119.8	C65—C64—H64	120.3
C24—C23—C22	120.49 (18)	C64—C65—C66	119.7 (3)
C24—C23—H23	119.8	C64—C65—H65	120.2
C22—C23—H23	119.8	C66—C65—H65	120.2
C23—C24—C25	119.20 (17)	C61—C66—C65	121.1 (2)
C23—C24—H24	120.4	C61—C66—H66	119.4
C25—C24—H24	120.4	C65—C66—H66	119.4
C26—C25—C24	120.56 (17)	C71—N7—C73	113.47 (15)
C26—C25—H25	119.7	C71—N7—C75	114.21 (15)
C24—C25—H25	119.7	C73—N7—C75	110.58 (14)
C25—C26—C21	120.55 (17)	C71—N7—H7	106.6 (12)
C25—C26—H26	119.7	C73—N7—H7	107.1 (12)
C21—C26—H26	119.7	C75—N7—H7	104.1 (12)
C36—C31—C32	119.05 (16)	N7—C71—C72	113.86 (17)
C36—C31—C2	120.90 (15)	N7—C71—H71A	108.8
C32—C31—C2	120.03 (15)	C72—C71—H71A	108.8
C33—C32—C31	120.62 (17)	N7—C71—H71B	108.8
C33—C32—H32	119.7	C72—C71—H71B	108.8
C31—C32—H32	119.7	H71A—C71—H71B	107.7
C32—C33—C34	120.00 (17)	C71—C72—H72A	109.5
C32—C33—H33	120.0	C71—C72—H72B	109.5
C34—C33—H33	120.0	H72A—C72—H72B	109.5
C35—C34—C33	119.42 (17)	C71—C72—H72C	109.5
C35—C34—H34	120.3	H72A—C72—H72C	109.5
C33—C34—H34	120.3	H72B—C72—H72C	109.5
C34—C35—C36	120.97 (17)	N7—C73—C74	112.90 (15)
C34—C35—H35	119.5	N7—C73—H73A	109.0
C36—C35—H35	119.5	C74—C73—H73A	109.0
C31—C36—C35	119.93 (17)	N7—C73—H73B	109.0
C31—C36—H36	120.0	C74—C73—H73B	109.0
C35—C36—H36	120.0	H73A—C73—H73B	107.8
C4—O4—Sb	116.24 (11)	C73—C74—H74A	109.5
O41—C4—O4	124.22 (17)	C73—C74—H74B	109.5
O41—C4—C5	120.70 (16)	H74A—C74—H74B	109.5
O4—C4—C5	115.08 (15)	C73—C74—H74C	109.5
O5—C5—C61	108.09 (14)	H74A—C74—H74C	109.5
O5—C5—C51	107.60 (13)	H74B—C74—H74C	109.5
C61—C5—C51	112.32 (14)	N7—C75—C76	111.77 (16)
O5—C5—C4	110.16 (14)	N7—C75—H75A	109.3
C61—C5—C4	111.56 (14)	C76—C75—H75A	109.3
C51—C5—C4	107.04 (14)	N7—C75—H75B	109.3
C5—O5—Sb	119.22 (10)	C76—C75—H75B	109.3
C56—C51—C52	118.33 (16)	H75A—C75—H75B	107.9
C56—C51—C5	123.58 (15)	C75—C76—H76A	109.5
C52—C51—C5	118.09 (15)	C75—C76—H76B	109.5
C53—C52—C51	120.98 (17)	H76A—C76—H76B	109.5
C53—C52—H52	119.5	C75—C76—H76C	109.5
C51—C52—H52	119.5	H76A—C76—H76C	109.5
C52—C53—C54	120.38 (18)	H76B—C76—H76C	109.5

O5—Sb—O1—C1	115.32 (12)	Sb—O4—C4—O41	178.69 (14)
O2—Sb—O1—C1	12.08 (11)	Sb—O4—C4—C5	−0.40 (18)
O4—Sb—O1—C1	61.90 (15)	O41—C4—C5—O5	−174.87 (16)
Sb—O1—C1—O11	177.04 (14)	O4—C4—C5—O5	4.3 (2)
Sb—O1—C1—C2	−2.13 (18)	O41—C4—C5—C61	65.1 (2)
O11—C1—C2—O2	167.18 (15)	O4—C4—C5—C61	−115.79 (16)
O1—C1—C2—O2	−13.6 (2)	O41—C4—C5—C51	−58.2 (2)
O11—C1—C2—C31	47.9 (2)	O4—C4—C5—C51	120.97 (16)
O1—C1—C2—C31	−132.91 (15)	C61—C5—O5—Sb	115.54 (12)
O11—C1—C2—C21	−73.93 (19)	C51—C5—O5—Sb	−122.94 (12)
O1—C1—C2—C21	105.29 (16)	C4—C5—O5—Sb	−6.58 (17)
C31—C2—O2—Sb	144.16 (10)	O2—Sb—O5—C5	−74.24 (11)
C21—C2—O2—Sb	−94.96 (13)	O4—Sb—O5—C5	5.13 (11)
C1—C2—O2—Sb	25.23 (16)	O1—Sb—O5—C5	−148.95 (11)
O5—Sb—O2—C2	−99.33 (11)	O5—C5—C51—C56	−125.51 (17)
O4—Sb—O2—C2	−176.37 (11)	C61—C5—C51—C56	−6.7 (2)
O1—Sb—O2—C2	−20.72 (10)	C4—C5—C51—C56	116.10 (19)
O2—C2—C21—C22	110.46 (18)	O5—C5—C51—C52	53.7 (2)
C31—C2—C21—C22	−129.76 (17)	C61—C5—C51—C52	172.54 (16)
C1—C2—C21—C22	−9.4 (2)	C4—C5—C51—C52	−64.69 (19)
O2—C2—C21—C26	−65.23 (18)	C56—C51—C52—C53	1.4 (3)
C31—C2—C21—C26	54.6 (2)	C5—C51—C52—C53	−177.87 (17)
C1—C2—C21—C26	174.93 (14)	C51—C52—C53—C54	−0.1 (3)
C26—C21—C22—C23	1.9 (3)	C52—C53—C54—C55	−0.8 (3)
C2—C21—C22—C23	−173.74 (16)	C53—C54—C55—C56	0.4 (3)
C21—C22—C23—C24	−1.1 (3)	C52—C51—C56—C55	−1.7 (3)
C22—C23—C24—C25	−0.2 (3)	C5—C51—C56—C55	177.48 (17)
C23—C24—C25—C26	0.7 (3)	C54—C55—C56—C51	0.8 (3)
C24—C25—C26—C21	0.2 (3)	O5—C5—C61—C62	−142.21 (17)
C22—C21—C26—C25	−1.5 (3)	C51—C5—C61—C62	99.2 (2)
C2—C21—C26—C25	174.40 (16)	C4—C5—C61—C62	−21.0 (2)
O2—C2—C31—C36	−14.4 (2)	O5—C5—C61—C66	39.1 (2)
C21—C2—C31—C36	−133.47 (17)	C51—C5—C61—C66	−79.4 (2)
C1—C2—C31—C36	105.21 (18)	C4—C5—C61—C66	160.38 (17)
O2—C2—C31—C32	167.26 (14)	C66—C61—C62—C63	−0.8 (3)
C21—C2—C31—C32	48.2 (2)	C5—C61—C62—C63	−179.45 (19)
C1—C2—C31—C32	−73.17 (19)	C61—C62—C63—C64	0.1 (4)
C36—C31—C32—C33	0.9 (3)	C62—C63—C64—C65	0.9 (4)
C2—C31—C32—C33	179.26 (16)	C63—C64—C65—C66	−1.3 (4)
C31—C32—C33—C34	0.1 (3)	C62—C61—C66—C65	0.5 (3)
C32—C33—C34—C35	−0.9 (3)	C5—C61—C66—C65	179.2 (2)
C33—C34—C35—C36	0.7 (3)	C64—C65—C66—C61	0.6 (4)
C32—C31—C36—C35	−1.1 (3)	C73—N7—C71—C72	60.8 (2)
C2—C31—C36—C35	−179.46 (16)	C75—N7—C71—C72	−67.2 (2)
C34—C35—C36—C31	0.3 (3)	C71—N7—C73—C74	56.6 (2)
O5—Sb—O4—C4	−2.44 (12)	C75—N7—C73—C74	−173.54 (16)
O2—Sb—O4—C4	100.31 (12)	C71—N7—C75—C76	−59.8 (2)
O1—Sb—O4—C4	51.60 (15)	C73—N7—C75—C76	170.79 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O11	0.93 (2)	1.78 (2)	2.706 (2)	177.5 (18)

Experimental details

Crystal data
Chemical formula	(C₆H₁₆N)[Sb(C₁₄H₁₀O₃)₂]
M_r	676.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	140
a, b, c (Å)	12.34379 (13), 10.63317 (12), 22.5264 (3)
β (°)	90.6466 (11)
V (Å³)	2956.49 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.98
Crystal size (mm)	0.28 × 0.27 × 0.09

Data collection
Diffractometer	Oxford Diffraction Xcalibur 3/CCD
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.911, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	61564, 6772, 5645
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.049, 1.01
No. of reflections	6772
No. of parameters	383
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.42

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), ORTEPII (Johnson, 1976) and ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

Sb—O1	2.2091 (12)	Sb—O4	2.1204 (12)
Sb—O2	1.9751 (11)	Sb—O5	1.9662 (11)

O2—Sb—O1	76.77 (4)	O2—Sb—O4	81.84 (5)
O4—Sb—O1	147.72 (5)	O5—Sb—O2	100.79 (5)
O5—Sb—O1	81.60 (5)	O5—Sb—O4	78.97 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O11	0.93 (2)	1.78 (2)	2.706 (2)	177.5 (18)

Footnotes

‡Currently at: Division of Environmental Materials, Faculty of Environmental Earth Science, Hokkaido University, Sapporo 060-0808, Japan.

Acknowledgements

MYR, MMH and MTHT thank Rajshahi University for provision of their central laboratory facilities. The authors also thank Dr Imroz Ali for his special assistance.

References

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