Di-n-butyl­ammonium 2-[(3,5-di-tert-butyl-4-hy­droxy­benz­yl)sulfan­yl]benzoate

Alhadi, A.A.; Khaledi, H.; Mohd Ali, H.; Olmstead, M.M.

doi:10.1107/S1600536810033921

organic compounds

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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page o2454

https://doi.org/10.1107/S1600536810033921

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Di-n-butylammonium 2-[(3,5-di-tert-butyl-4-hydroxybenzyl)sulfanyl]benzoate

Abeer A. Alhadi,^a Hamid Khaledi,^a ^* Hapipah Mohd Ali ^a and Marilyn M. Olmstead ^b

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^bDepartment of Chemistry, University of California, One Shields Avenue, Davis, CA 95616, USA
^*Correspondence e-mail: khaledi@siswa.um.edu.my

(Received 16 July 2010; accepted 23 August 2010; online 28 August 2010)

The title salt, C₈H₂₀N⁺·C₂₂H₂₇O₃S⁻, is a proton-transfer compound derived from the recently reported parent carboxylic acid [Alhadi et al. (2010). Acta Cryst. E66, o1787] by the addition of a second equivalent of di-n-butylamine, yielding the di-n-butylammonium carboxylate salt. The structure of the carboxylate anion resembles that of the parent carboxylic acid. The main difference lies in the position of the H atom in the 4-hydroxy 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 carboxylate 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_r = 501.75
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.050
wR(F²) = 0.138
S = 1.01
5277 reflections
333 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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) x+1, y, z; (ii) -x+1, -y, -z+1.

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 ).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810033921/bh2302Isup2.hkl

checkCIF report

Comment top

As shown in Fig. 1, the title compound is a di-n-butylammonium salt. It is a proton transfer derivative of the previously reported benzoic acid analog (Alhadi et al., 2010). In contrast to the structure of the parent carboxylic acid in which the C—O—H fragment was found coplanar to the aromatic ring and therefore not involved in any hydrogen bonding, in the present structure the O—H bond is perpendicular to the aromatic ring, and it participates in hydrogen bonding to the carboxylate group of the neighboring anion, forming an infinite chain along the a axis (Fig. 2). This arrangement is similar to that reported for the salt based on nicotinic acid (Mansor et al., 2008). The dihedral angle between the aromatic rings C2/C3/C4/C5/C6/C7 and C9/C10/C11/C12/C13/C14 is 79.19 (7)°.

Related literature top

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 top

Thiosalicylic acid (0.154 g, 1 mmol), 2,6-di-t-butylphenol (2.00 g, 1 mmol) and paraformaldehyde (0.291 g, 1 mmol) were ground into a homogenous powder and to this was added di-n-butylamine (0.1 ml). The slurry was heated to 353 K for 2.5 h, then cooled to 323 K. Ethanol (20 ml) was added and the mixture was stirred for 1 h at room temperature. To the resulting clear solution di-n-butylamine (0.1 ml) was added and the solution was set aside in the dark for 5 days whereupon the colorless crystals of the title compound were obtained.

Structure description top

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).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

	Fig. 1. Thermal ellipsoid plot of the title compound at the 30% probability level. H atoms participating in hydrogen bonding are drawn as spheres of arbitrary radius.
	Fig. 2. A view of the hydrogen bonding interactions (dashed lines) as viewed down b. Symmetry codes: ' = x - 1, y, z; " = -x + 1, -y, -z + 1.

Di-n-butylammonium 2-[(3,5-di-tert-butyl-4-hydroxybenzyl)sulfanyl]benzoate top

Crystal data top

C₈H₂₀N⁺·C₂₂H₂₇O₃S⁻	F(000) = 2192
M_r = 501.75	D_x = 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

Data collection top

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

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)] = 0.050	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(F_o²) + (0.0533P)² + 2.2704P] where P = (F_o² + 2F_c²)/3
5277 reflections	(Δ/σ)_max < 0.001
333 parameters	Δρ_max = 0.28 e Å⁻³
3 restraints	Δρ_min = −0.17 e Å⁻³
0 constraints

Crystal data top

C₈H₂₀N⁺·C₂₂H₂₇O₃S⁻	V = 5973.9 (4) Å³
M_r = 501.75	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 12.8631 (5) Å	µ = 0.14 mm⁻¹
b = 20.1109 (9) Å	T = 296 K
c = 23.0930 (9) Å	0.60 × 0.40 × 0.35 mm

Data collection top

Bruker APEXII diffractometer	5277 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3311 reflections with I > 2σ(I)
T_min = 0.922, T_max = 0.954	R_int = 0.080
44646 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	3 restraints
wR(F²) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.28 e Å⁻³
5277 reflections	Δρ_min = −0.17 e Å⁻³
333 parameters

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z; (ii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₈H₂₀N⁺·C₂₂H₂₇O₃S⁻
M_r	501.75
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	12.8631 (5), 20.1109 (9), 23.0930 (9)
V (Å³)	5973.9 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.60 × 0.40 × 0.35

Data collection
Diffractometer	Bruker APEXII
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.922, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	44646, 5277, 3311
R_int	0.080
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.138, 1.01
No. of reflections	5277
No. of parameters	333
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.17

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Bruker, 2007), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1ⁱ	0.806 (18)	2.02 (2)	2.723 (3)	146 (3)
N1—H1A···O2	0.890 (17)	1.878 (17)	2.767 (3)	177 (3)
N1—H1B···O1ⁱⁱ	0.892 (17)	2.00 (2)	2.806 (3)	150 (3)
N1—H1B···O2ⁱⁱ	0.892 (17)	2.36 (2)	3.167 (3)	150 (2)
N1—H1B···O2ⁱⁱ	0.892 (17)	2.36 (2)	3.167 (3)	150 (2)

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z+1.

Acknowledgements

The authors thank the University of Malaya for funding this study (FRGS grant FP009/2008 C).

References

Alhadi, A. A., Khaledi, H., Mohd Ali, H. & Olmstead, M. M. (2010). Acta Cryst. E66, o1787. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2007). APEX2, SAINT and XP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Mansor, S., Yehye, W. A., Ariffin, A., Rahman, N. A. & Ng, S. W. (2008). Acta Cryst. E64, o1799. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Di-n-butyl­ammonium 2-[(3,5-di-tert-butyl-4-hy­dr­oxy­benz­yl)sulfan­yl]benzoate

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Experimental

Crystal data

Data collection

Refinement

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organic compounds

Di-n-butylammonium 2-[(3,5-di-tert-butyl-4-hydroxybenzyl)sulfanyl]benzoate