Di-n-butyl-ammonium 2-[(3,5-di-tert-butyl-4-hy-droxy-benz-yl)sulfan-yl]benzoate.

The title salt, C(8)H(20)N(+)·C(22)H(27)O(3)S(-), is a proton-transfer compound derived from the recently reported parent carb-oxy-lic acid [Alhadi et al. (2010). Acta Cryst. E66, o1787] by the addition of a second equivalent of di-n-butyl-amine, yielding the di-n-butyl-ammonium carboxyl-ate salt. The structure of the carboxyl-ate anion resembles that of the parent carb-oxy-lic acid. The main difference lies in the position of the H atom in the 4-hy-droxy group. In the anion the O-H bond is perpendicular, rather than parallel, to the benzyl ring. This position appears to facilitate hydrogen bonding to an O atom of the carboxyl-ate group of a symmetry-related anion. In addition, there are three N-H⋯O hydrogen bonds. In contrast, the neutral species hydrogen bonds via a carboxylic acid dimer. The dihedral angle between the benzene rings in the anion is 79.19 (7)°.

Related literature

For the structure of the parent benzoic acid, see: Alhadi et al. (2010 ▶). For a similar structure based on nicotinic acid, see: Mansor et al. (2008 ▶).

Experimental

Crystal data

C8H20N+·C22H27O3S−

M = 501.75

Orthorhombic,

a = 12.8631 (5) Å

b = 20.1109 (9) Å

c = 23.0930 (9) Å

V = 5973.9 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.14 mm−1

T = 296 K

0.60 × 0.40 × 0.35 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.922, T max = 0.954

44646 measured reflections

5277 independent reflections

3311 reflections with I > 2σ(I)

R int = 0.080

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.138

S = 1.01

5277 reflections

333 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Bruker, 2007 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810033921/bh2302sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033921/bh2302Isup2.hkl

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

C8H20N+·C22H27O3S−	F(000) = 2192
Mr = 501.75	Dx = 1.116 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3944 reflections
a = 12.8631 (5) Å	θ = 2.4–19.4°
b = 20.1109 (9) Å	µ = 0.14 mm−1
c = 23.0930 (9) Å	T = 296 K
V = 5973.9 (4) Å3	Irregular block, colourless
Z = 8	0.60 × 0.40 × 0.35 mm

Bruker APEXII diffractometer	5277 independent reflections
Radiation source: fine-focus sealed tube	3311 reflections with I > 2σ(I)
graphite	Rint = 0.080
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→15
Tmin = 0.922, Tmax = 0.954	k = −23→23
44646 measured reflections	l = −27→27

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0533P)2 + 2.2704P] where P = (Fo2 + 2Fc2)/3
5277 reflections	(Δ/σ)max < 0.001
333 parameters	Δρmax = 0.28 e Å−3
3 restraints	Δρmin = −0.17 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
C1	0.4142 (2)	0.10279 (13)	0.41431 (11)	0.0573 (7)
S1	0.64187 (5)	0.14037 (4)	0.37500 (3)	0.0571 (2)
O1	0.32489 (16)	0.08674 (12)	0.42807 (11)	0.1060 (9)
O2	0.49152 (15)	0.07570 (10)	0.43550 (9)	0.0799 (6)
O3	1.11548 (13)	0.06947 (10)	0.41947 (9)	0.0676 (5)
H3	1.1701 (18)	0.0878 (16)	0.4133 (14)	0.101*
N1	0.65789 (17)	0.01880 (12)	0.49304 (11)	0.0639 (6)
H1A	0.6030 (17)	0.0360 (13)	0.4749 (11)	0.077*
H1B	0.639 (2)	−0.0157 (11)	0.5148 (11)	0.077*
C2	0.42822 (17)	0.15713 (11)	0.37050 (9)	0.0443 (6)
C3	0.34012 (19)	0.18891 (13)	0.34973 (11)	0.0552 (6)
H3A	0.2754	0.1757	0.3635	0.066*
C4	0.3448 (2)	0.23882 (15)	0.30980 (12)	0.0669 (8)
H4	0.2843	0.2591	0.2966	0.080*
C5	0.4395 (2)	0.25874 (15)	0.28939 (13)	0.0732 (9)
H5	0.4436	0.2928	0.2623	0.088*
C6	0.5294 (2)	0.22837 (14)	0.30893 (12)	0.0648 (7)
H6	0.5934	0.2422	0.2945	0.078*
C7	0.52605 (17)	0.17767 (12)	0.34970 (10)	0.0459 (6)
C8	0.74329 (17)	0.18495 (13)	0.33648 (11)	0.0579 (7)
H8A	0.7354	0.1789	0.2950	0.069*
H8B	0.7394	0.2321	0.3450	0.069*
C9	0.84580 (18)	0.15715 (13)	0.35632 (11)	0.0512 (6)
C10	0.89894 (18)	0.11082 (12)	0.32410 (11)	0.0516 (6)
H10	0.8716	0.0979	0.2885	0.062*
C11	0.99201 (17)	0.08236 (12)	0.34249 (10)	0.0482 (6)
C12	1.02979 (17)	0.10199 (12)	0.39672 (10)	0.0486 (6)
C13	0.97987 (18)	0.15064 (13)	0.43035 (10)	0.0524 (6)
C14	0.88760 (18)	0.17683 (13)	0.40858 (11)	0.0556 (7)
H14	0.8527	0.2089	0.4302	0.067*
C15	1.0201 (2)	0.17282 (17)	0.49001 (12)	0.0734 (9)
C16	0.9545 (3)	0.2305 (2)	0.51411 (17)	0.1397 (19)
H16A	0.9577	0.2675	0.4879	0.209*
H16B	0.9814	0.2436	0.5512	0.209*
H16C	0.8837	0.2164	0.5183	0.209*
C17	1.0103 (3)	0.1149 (2)	0.53240 (13)	0.1155 (15)
H17A	1.0507	0.0780	0.5186	0.173*
H17B	0.9387	0.1020	0.5355	0.173*
H17C	1.0354	0.1284	0.5697	0.173*
C18	1.1328 (2)	0.19722 (19)	0.48760 (15)	0.0960 (11)
H18A	1.1779	0.1605	0.4790	0.144*
H18B	1.1516	0.2161	0.5243	0.144*
H18C	1.1395	0.2304	0.4579	0.144*
C19	1.04977 (19)	0.03203 (13)	0.30369 (11)	0.0579 (7)
C20	0.9917 (2)	0.02028 (16)	0.24637 (13)	0.0822 (9)
H20A	1.0298	−0.0109	0.2231	0.123*
H20B	0.9854	0.0616	0.2258	0.123*
H20C	0.9237	0.0028	0.2543	0.123*
C21	1.1572 (2)	0.05973 (17)	0.28782 (13)	0.0846 (10)
H21A	1.2001	0.0610	0.3218	0.127*
H21B	1.1497	0.1039	0.2725	0.127*
H21C	1.1889	0.0317	0.2592	0.127*
C22	1.0605 (2)	−0.03551 (15)	0.33351 (14)	0.0824 (9)
H22A	1.0975	−0.0655	0.3086	0.124*
H22B	0.9926	−0.0532	0.3415	0.124*
H22C	1.0980	−0.0302	0.3691	0.124*
C23	0.7166 (4)	−0.1192 (2)	0.3170 (2)	0.1382 (17)
H23A	0.6944	−0.1593	0.3359	0.207*
H23B	0.7700	−0.1295	0.2894	0.207*
H23C	0.6585	−0.0993	0.2974	0.207*
C24	0.7569 (3)	−0.0731 (3)	0.35968 (18)	0.1261 (15)
H24A	0.7790	−0.0331	0.3397	0.151*
H24B	0.8183	−0.0928	0.3771	0.151*
C25	0.6833 (3)	−0.05329 (18)	0.40777 (15)	0.0897 (10)
H25A	0.6222	−0.0325	0.3910	0.108*
H25B	0.6608	−0.0929	0.4283	0.108*
C26	0.7327 (2)	−0.00614 (17)	0.44985 (13)	0.0771 (9)
H26A	0.7892	−0.0286	0.4696	0.093*
H26B	0.7619	0.0312	0.4288	0.093*
C27	0.7013 (2)	0.06935 (16)	0.53258 (14)	0.0783 (9)
H27A	0.7257	0.1071	0.5102	0.094*
H27B	0.7603	0.0507	0.5530	0.094*
C28	0.6206 (3)	0.09282 (17)	0.57620 (15)	0.0901 (10)
H28A	0.5647	0.1150	0.5557	0.108*
H28B	0.5914	0.0544	0.5957	0.108*
C29	0.6642 (3)	0.1391 (2)	0.62032 (18)	0.1121 (13)
H29A	0.6988	0.1755	0.6006	0.135*
H29B	0.7160	0.1157	0.6430	0.135*
C30	0.5837 (3)	0.1671 (3)	0.6604 (2)	0.1449 (18)
H30A	0.5335	0.1918	0.6384	0.217*
H30B	0.6164	0.1959	0.6880	0.217*
H30C	0.5494	0.1314	0.6804	0.217*

	U11	U22	U33	U12	U13	U23
C1	0.0437 (15)	0.0638 (17)	0.0644 (17)	0.0003 (14)	0.0004 (13)	0.0071 (14)
S1	0.0381 (3)	0.0675 (4)	0.0658 (4)	0.0052 (3)	−0.0047 (3)	0.0172 (3)
O1	0.0492 (12)	0.1187 (19)	0.150 (2)	−0.0007 (12)	0.0137 (13)	0.0679 (17)
O2	0.0560 (12)	0.0903 (15)	0.0934 (15)	0.0010 (11)	−0.0136 (10)	0.0372 (12)
O3	0.0384 (10)	0.0833 (14)	0.0810 (13)	0.0067 (10)	−0.0051 (9)	0.0132 (11)
N1	0.0461 (13)	0.0715 (17)	0.0741 (17)	−0.0010 (12)	−0.0089 (12)	0.0213 (13)
C2	0.0394 (13)	0.0497 (14)	0.0437 (13)	0.0041 (11)	−0.0048 (10)	−0.0035 (11)
C3	0.0408 (14)	0.0645 (17)	0.0603 (16)	0.0078 (12)	−0.0032 (12)	−0.0009 (14)
C4	0.0497 (16)	0.080 (2)	0.0707 (18)	0.0224 (15)	−0.0118 (13)	0.0079 (16)
C5	0.0632 (18)	0.080 (2)	0.076 (2)	0.0161 (16)	−0.0034 (15)	0.0288 (16)
C6	0.0465 (15)	0.0763 (19)	0.0715 (18)	0.0088 (14)	0.0009 (13)	0.0221 (16)
C7	0.0400 (13)	0.0513 (14)	0.0462 (14)	0.0064 (11)	−0.0047 (10)	0.0040 (12)
C8	0.0407 (14)	0.0651 (17)	0.0679 (17)	0.0015 (13)	−0.0041 (12)	0.0126 (14)
C9	0.0388 (13)	0.0586 (16)	0.0562 (15)	−0.0020 (12)	−0.0018 (11)	0.0095 (12)
C10	0.0429 (13)	0.0609 (16)	0.0510 (15)	−0.0045 (13)	−0.0015 (11)	0.0036 (13)
C11	0.0379 (13)	0.0557 (15)	0.0512 (15)	−0.0006 (11)	0.0068 (11)	0.0065 (12)
C12	0.0309 (12)	0.0614 (16)	0.0536 (15)	−0.0005 (12)	0.0056 (11)	0.0088 (12)
C13	0.0375 (13)	0.0700 (17)	0.0497 (15)	−0.0021 (12)	0.0020 (11)	0.0026 (13)
C14	0.0413 (14)	0.0644 (17)	0.0612 (17)	0.0033 (12)	0.0051 (12)	−0.0020 (13)
C15	0.0501 (16)	0.113 (2)	0.0569 (18)	0.0101 (17)	−0.0042 (13)	−0.0163 (17)
C16	0.106 (3)	0.208 (5)	0.105 (3)	0.055 (3)	−0.034 (2)	−0.092 (3)
C17	0.072 (2)	0.217 (5)	0.058 (2)	−0.007 (3)	−0.0067 (17)	0.031 (3)
C18	0.070 (2)	0.128 (3)	0.090 (2)	−0.016 (2)	−0.0125 (17)	−0.031 (2)
C19	0.0473 (15)	0.0646 (17)	0.0616 (17)	0.0025 (13)	0.0091 (12)	−0.0025 (14)
C20	0.084 (2)	0.091 (2)	0.071 (2)	0.0077 (18)	0.0033 (17)	−0.0192 (18)
C21	0.0661 (19)	0.102 (3)	0.086 (2)	−0.0117 (18)	0.0308 (16)	−0.0162 (19)
C22	0.079 (2)	0.069 (2)	0.099 (2)	0.0095 (17)	0.0052 (18)	0.0039 (18)
C23	0.154 (4)	0.123 (3)	0.138 (4)	0.040 (3)	−0.021 (3)	−0.026 (3)
C24	0.081 (3)	0.181 (5)	0.116 (3)	0.021 (3)	−0.007 (2)	−0.011 (3)
C25	0.071 (2)	0.099 (3)	0.099 (3)	0.0172 (19)	−0.0035 (19)	0.003 (2)
C26	0.0496 (17)	0.098 (2)	0.084 (2)	0.0130 (17)	−0.0005 (15)	0.0249 (19)
C27	0.0577 (18)	0.088 (2)	0.089 (2)	−0.0107 (17)	−0.0169 (16)	0.0154 (18)
C28	0.069 (2)	0.095 (3)	0.107 (3)	−0.0073 (19)	−0.0078 (19)	−0.009 (2)
C29	0.090 (3)	0.130 (3)	0.117 (3)	−0.010 (2)	−0.009 (2)	−0.021 (3)
C30	0.105 (3)	0.183 (5)	0.147 (4)	−0.021 (3)	0.022 (3)	−0.055 (4)

C1—O2	1.235 (3)	C17—H17B	0.9600
C1—O1	1.235 (3)	C17—H17C	0.9600
C1—C2	1.500 (3)	C18—H18A	0.9600
S1—C7	1.767 (2)	C18—H18B	0.9600
S1—C8	1.816 (2)	C18—H18C	0.9600
O3—C12	1.385 (3)	C19—C22	1.529 (4)
O3—H3	0.806 (18)	C19—C21	1.534 (4)
N1—C26	1.474 (4)	C19—C20	1.538 (4)
N1—C27	1.476 (4)	C20—H20A	0.9600
N1—H1A	0.890 (17)	C20—H20B	0.9600
N1—H1B	0.892 (17)	C20—H20C	0.9600
C2—C3	1.387 (3)	C21—H21A	0.9600
C2—C7	1.409 (3)	C21—H21B	0.9600
C3—C4	1.364 (4)	C21—H21C	0.9600
C3—H3A	0.9300	C22—H22A	0.9600
C4—C5	1.366 (4)	C22—H22B	0.9600
C4—H4	0.9300	C22—H22C	0.9600
C5—C6	1.383 (3)	C23—C24	1.450 (5)
C5—H5	0.9300	C23—H23A	0.9600
C6—C7	1.389 (3)	C23—H23B	0.9600
C6—H6	0.9300	C23—H23C	0.9600
C8—C9	1.504 (3)	C24—C25	1.513 (5)
C8—H8A	0.9700	C24—H24A	0.9700
C8—H8B	0.9700	C24—H24B	0.9700
C9—C10	1.374 (3)	C25—C26	1.499 (4)
C9—C14	1.379 (3)	C25—H25A	0.9700
C10—C11	1.393 (3)	C25—H25B	0.9700
C10—H10	0.9300	C26—H26A	0.9700
C11—C12	1.400 (3)	C26—H26B	0.9700
C11—C19	1.543 (3)	C27—C28	1.521 (4)
C12—C13	1.405 (3)	C27—H27A	0.9700
C13—C14	1.392 (3)	C27—H27B	0.9700
C13—C15	1.538 (4)	C28—C29	1.490 (5)
C14—H14	0.9300	C28—H28A	0.9700
C15—C17	1.526 (5)	C28—H28B	0.9700
C15—C18	1.532 (4)	C29—C30	1.498 (5)
C15—C16	1.538 (4)	C29—H29A	0.9700
C16—H16A	0.9600	C29—H29B	0.9700
C16—H16B	0.9600	C30—H30A	0.9600
C16—H16C	0.9600	C30—H30B	0.9600
C17—H17A	0.9600	C30—H30C	0.9600
O2—C1—O1	122.1 (3)	H18A—C18—H18C	109.5
O2—C1—C2	119.5 (2)	H18B—C18—H18C	109.5
O1—C1—C2	118.4 (2)	C22—C19—C21	110.4 (2)
C7—S1—C8	103.55 (11)	C22—C19—C20	107.2 (2)
C12—O3—H3	114 (3)	C21—C19—C20	106.7 (2)
C26—N1—C27	114.0 (2)	C22—C19—C11	111.4 (2)
C26—N1—H1A	109.4 (18)	C21—C19—C11	109.5 (2)
C27—N1—H1A	108.8 (18)	C20—C19—C11	111.5 (2)
C26—N1—H1B	107.3 (18)	C19—C20—H20A	109.5
C27—N1—H1B	106.9 (18)	C19—C20—H20B	109.5
H1A—N1—H1B	110 (3)	H20A—C20—H20B	109.5
C3—C2—C7	118.5 (2)	C19—C20—H20C	109.5
C3—C2—C1	118.1 (2)	H20A—C20—H20C	109.5
C7—C2—C1	123.4 (2)	H20B—C20—H20C	109.5
C4—C3—C2	122.5 (2)	C19—C21—H21A	109.5
C4—C3—H3A	118.8	C19—C21—H21B	109.5
C2—C3—H3A	118.8	H21A—C21—H21B	109.5
C3—C4—C5	119.2 (2)	C19—C21—H21C	109.5
C3—C4—H4	120.4	H21A—C21—H21C	109.5
C5—C4—H4	120.4	H21B—C21—H21C	109.5
C4—C5—C6	120.2 (3)	C19—C22—H22A	109.5
C4—C5—H5	119.9	C19—C22—H22B	109.5
C6—C5—H5	119.9	H22A—C22—H22B	109.5
C5—C6—C7	121.3 (2)	C19—C22—H22C	109.5
C5—C6—H6	119.4	H22A—C22—H22C	109.5
C7—C6—H6	119.4	H22B—C22—H22C	109.5
C6—C7—C2	118.3 (2)	C24—C23—H23A	109.5
C6—C7—S1	120.62 (18)	C24—C23—H23B	109.5
C2—C7—S1	121.05 (17)	H23A—C23—H23B	109.5
C9—C8—S1	107.30 (17)	C24—C23—H23C	109.5
C9—C8—H8A	110.3	H23A—C23—H23C	109.5
S1—C8—H8A	110.3	H23B—C23—H23C	109.5
C9—C8—H8B	110.3	C23—C24—C25	116.3 (4)
S1—C8—H8B	110.3	C23—C24—H24A	108.2
H8A—C8—H8B	108.5	C25—C24—H24A	108.2
C10—C9—C14	118.3 (2)	C23—C24—H24B	108.2
C10—C9—C8	121.6 (2)	C25—C24—H24B	108.2
C14—C9—C8	120.1 (2)	H24A—C24—H24B	107.4
C9—C10—C11	122.7 (2)	C26—C25—C24	112.1 (3)
C9—C10—H10	118.6	C26—C25—H25A	109.2
C11—C10—H10	118.6	C24—C25—H25A	109.2
C10—C11—C12	117.1 (2)	C26—C25—H25B	109.2
C10—C11—C19	120.4 (2)	C24—C25—H25B	109.2
C12—C11—C19	122.5 (2)	H25A—C25—H25B	107.9
O3—C12—C11	118.8 (2)	N1—C26—C25	112.2 (2)
O3—C12—C13	118.9 (2)	N1—C26—H26A	109.2
C11—C12—C13	122.2 (2)	C25—C26—H26A	109.2
C14—C13—C12	117.0 (2)	N1—C26—H26B	109.2
C14—C13—C15	120.0 (2)	C25—C26—H26B	109.2
C12—C13—C15	122.9 (2)	H26A—C26—H26B	107.9
C9—C14—C13	122.7 (2)	N1—C27—C28	111.4 (2)
C9—C14—H14	118.7	N1—C27—H27A	109.3
C13—C14—H14	118.7	C28—C27—H27A	109.3
C17—C15—C18	110.2 (3)	N1—C27—H27B	109.3
C17—C15—C13	109.0 (3)	C28—C27—H27B	109.3
C18—C15—C13	112.2 (2)	H27A—C27—H27B	108.0
C17—C15—C16	107.4 (3)	C29—C28—C27	113.0 (3)
C18—C15—C16	106.9 (3)	C29—C28—H28A	109.0
C13—C15—C16	111.0 (2)	C27—C28—H28A	109.0
C15—C16—H16A	109.5	C29—C28—H28B	109.0
C15—C16—H16B	109.5	C27—C28—H28B	109.0
H16A—C16—H16B	109.5	H28A—C28—H28B	107.8
C15—C16—H16C	109.5	C28—C29—C30	113.4 (3)
H16A—C16—H16C	109.5	C28—C29—H29A	108.9
H16B—C16—H16C	109.5	C30—C29—H29A	108.9
C15—C17—H17A	109.5	C28—C29—H29B	108.9
C15—C17—H17B	109.5	C30—C29—H29B	108.9
H17A—C17—H17B	109.5	H29A—C29—H29B	107.7
C15—C17—H17C	109.5	C29—C30—H30A	109.5
H17A—C17—H17C	109.5	C29—C30—H30B	109.5
H17B—C17—H17C	109.5	H30A—C30—H30B	109.5
C15—C18—H18A	109.5	C29—C30—H30C	109.5
C15—C18—H18B	109.5	H30A—C30—H30C	109.5
H18A—C18—H18B	109.5	H30B—C30—H30C	109.5
C15—C18—H18C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1i	0.81 (2)	2.02 (2)	2.723 (3)	146 (3)
N1—H1A···O2	0.89 (2)	1.88 (2)	2.767 (3)	177 (3)
N1—H1B···O1ii	0.89 (2)	2.00 (2)	2.806 (3)	150 (3)
N1—H1B···O2ii	0.89 (2)	2.36 (2)	3.167 (3)	150 (2)
N1—H1B···O2ii	0.89 (2)	2.36 (2)	3.167 (3)	150 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1i	0.81 (2)	2.02 (2)	2.723 (3)	146 (3)
N1—H1A⋯O2	0.89 (2)	1.88 (2)	2.767 (3)	177 (3)
N1—H1B⋯O1ii	0.89 (2)	2.00 (2)	2.806 (3)	150 (3)
N1—H1B⋯O2ii	0.89 (2)	2.36 (2)	3.167 (3)	150 (2)
N1—H1B⋯O2ii	0.89 (2)	2.36 (2)	3.167 (3)	150 (2)

Symmetry codes: (i) ; (ii) .