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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): o2454.
Published online 2010 August 28. doi:  10.1107/S1600536810033921
PMCID: PMC3007956

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

Abstract

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 [triangle]). For a similar structure based on nicotinic acid, see: Mansor et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2454-scheme1.jpg

Experimental

Crystal data

  • C8H20N+·C22H27O3S
  • M r = 501.75
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2454-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: XP (Bruker, 2007 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

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

supplementary crystallographic information

Comment

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)°.

Experimental

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.

Refinement

The C-bound hydrogen atoms were placed at calculated positions (C—H 0.93–0.97 Å) and were treated as riding on their parent atoms. The nitrogen- and oxygen-bound hydrogen atoms were located in a difference map and were refined freely with distances restrained to N—H 0.86 (2) and O—H 0.82 (2) Å. For all H atoms, Uiso(H) was set to 1.2–1.5 Ueq(carrier atom).

Figures

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.

Crystal data

C8H20N+·C22H27O3SF(000) = 2192
Mr = 501.75Dx = 1.116 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3944 reflections
a = 12.8631 (5) Åθ = 2.4–19.4°
b = 20.1109 (9) ŵ = 0.14 mm1
c = 23.0930 (9) ÅT = 296 K
V = 5973.9 (4) Å3Irregular block, colourless
Z = 80.60 × 0.40 × 0.35 mm

Data collection

Bruker APEXII diffractometer5277 independent reflections
Radiation source: fine-focus sealed tube3311 reflections with I > 2σ(I)
graphiteRint = 0.080
[var phi] and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −15→15
Tmin = 0.922, Tmax = 0.954k = −23→23
44646 measured reflectionsl = −27→27

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H atoms treated by a mixture of independent and constrained refinement
S = 1.01w = 1/[σ2(Fo2) + (0.0533P)2 + 2.2704P] where P = (Fo2 + 2Fc2)/3
5277 reflections(Δ/σ)max < 0.001
333 parametersΔρmax = 0.28 e Å3
3 restraintsΔρmin = −0.17 e Å3
0 constraints

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

xyzUiso*/Ueq
C10.4142 (2)0.10279 (13)0.41431 (11)0.0573 (7)
S10.64187 (5)0.14037 (4)0.37500 (3)0.0571 (2)
O10.32489 (16)0.08674 (12)0.42807 (11)0.1060 (9)
O20.49152 (15)0.07570 (10)0.43550 (9)0.0799 (6)
O31.11548 (13)0.06947 (10)0.41947 (9)0.0676 (5)
H31.1701 (18)0.0878 (16)0.4133 (14)0.101*
N10.65789 (17)0.01880 (12)0.49304 (11)0.0639 (6)
H1A0.6030 (17)0.0360 (13)0.4749 (11)0.077*
H1B0.639 (2)−0.0157 (11)0.5148 (11)0.077*
C20.42822 (17)0.15713 (11)0.37050 (9)0.0443 (6)
C30.34012 (19)0.18891 (13)0.34973 (11)0.0552 (6)
H3A0.27540.17570.36350.066*
C40.3448 (2)0.23882 (15)0.30980 (12)0.0669 (8)
H40.28430.25910.29660.080*
C50.4395 (2)0.25874 (15)0.28939 (13)0.0732 (9)
H50.44360.29280.26230.088*
C60.5294 (2)0.22837 (14)0.30893 (12)0.0648 (7)
H60.59340.24220.29450.078*
C70.52605 (17)0.17767 (12)0.34970 (10)0.0459 (6)
C80.74329 (17)0.18495 (13)0.33648 (11)0.0579 (7)
H8A0.73540.17890.29500.069*
H8B0.73940.23210.34500.069*
C90.84580 (18)0.15715 (13)0.35632 (11)0.0512 (6)
C100.89894 (18)0.11082 (12)0.32410 (11)0.0516 (6)
H100.87160.09790.28850.062*
C110.99201 (17)0.08236 (12)0.34249 (10)0.0482 (6)
C121.02979 (17)0.10199 (12)0.39672 (10)0.0486 (6)
C130.97987 (18)0.15064 (13)0.43035 (10)0.0524 (6)
C140.88760 (18)0.17683 (13)0.40858 (11)0.0556 (7)
H140.85270.20890.43020.067*
C151.0201 (2)0.17282 (17)0.49001 (12)0.0734 (9)
C160.9545 (3)0.2305 (2)0.51411 (17)0.1397 (19)
H16A0.95770.26750.48790.209*
H16B0.98140.24360.55120.209*
H16C0.88370.21640.51830.209*
C171.0103 (3)0.1149 (2)0.53240 (13)0.1155 (15)
H17A1.05070.07800.51860.173*
H17B0.93870.10200.53550.173*
H17C1.03540.12840.56970.173*
C181.1328 (2)0.19722 (19)0.48760 (15)0.0960 (11)
H18A1.17790.16050.47900.144*
H18B1.15160.21610.52430.144*
H18C1.13950.23040.45790.144*
C191.04977 (19)0.03203 (13)0.30369 (11)0.0579 (7)
C200.9917 (2)0.02028 (16)0.24637 (13)0.0822 (9)
H20A1.0298−0.01090.22310.123*
H20B0.98540.06160.22580.123*
H20C0.92370.00280.25430.123*
C211.1572 (2)0.05973 (17)0.28782 (13)0.0846 (10)
H21A1.20010.06100.32180.127*
H21B1.14970.10390.27250.127*
H21C1.18890.03170.25920.127*
C221.0605 (2)−0.03551 (15)0.33351 (14)0.0824 (9)
H22A1.0975−0.06550.30860.124*
H22B0.9926−0.05320.34150.124*
H22C1.0980−0.03020.36910.124*
C230.7166 (4)−0.1192 (2)0.3170 (2)0.1382 (17)
H23A0.6944−0.15930.33590.207*
H23B0.7700−0.12950.28940.207*
H23C0.6585−0.09930.29740.207*
C240.7569 (3)−0.0731 (3)0.35968 (18)0.1261 (15)
H24A0.7790−0.03310.33970.151*
H24B0.8183−0.09280.37710.151*
C250.6833 (3)−0.05329 (18)0.40777 (15)0.0897 (10)
H25A0.6222−0.03250.39100.108*
H25B0.6608−0.09290.42830.108*
C260.7327 (2)−0.00614 (17)0.44985 (13)0.0771 (9)
H26A0.7892−0.02860.46960.093*
H26B0.76190.03120.42880.093*
C270.7013 (2)0.06935 (16)0.53258 (14)0.0783 (9)
H27A0.72570.10710.51020.094*
H27B0.76030.05070.55300.094*
C280.6206 (3)0.09282 (17)0.57620 (15)0.0901 (10)
H28A0.56470.11500.55570.108*
H28B0.59140.05440.59570.108*
C290.6642 (3)0.1391 (2)0.62032 (18)0.1121 (13)
H29A0.69880.17550.60060.135*
H29B0.71600.11570.64300.135*
C300.5837 (3)0.1671 (3)0.6604 (2)0.1449 (18)
H30A0.53350.19180.63840.217*
H30B0.61640.19590.68800.217*
H30C0.54940.13140.68040.217*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0437 (15)0.0638 (17)0.0644 (17)0.0003 (14)0.0004 (13)0.0071 (14)
S10.0381 (3)0.0675 (4)0.0658 (4)0.0052 (3)−0.0047 (3)0.0172 (3)
O10.0492 (12)0.1187 (19)0.150 (2)−0.0007 (12)0.0137 (13)0.0679 (17)
O20.0560 (12)0.0903 (15)0.0934 (15)0.0010 (11)−0.0136 (10)0.0372 (12)
O30.0384 (10)0.0833 (14)0.0810 (13)0.0067 (10)−0.0051 (9)0.0132 (11)
N10.0461 (13)0.0715 (17)0.0741 (17)−0.0010 (12)−0.0089 (12)0.0213 (13)
C20.0394 (13)0.0497 (14)0.0437 (13)0.0041 (11)−0.0048 (10)−0.0035 (11)
C30.0408 (14)0.0645 (17)0.0603 (16)0.0078 (12)−0.0032 (12)−0.0009 (14)
C40.0497 (16)0.080 (2)0.0707 (18)0.0224 (15)−0.0118 (13)0.0079 (16)
C50.0632 (18)0.080 (2)0.076 (2)0.0161 (16)−0.0034 (15)0.0288 (16)
C60.0465 (15)0.0763 (19)0.0715 (18)0.0088 (14)0.0009 (13)0.0221 (16)
C70.0400 (13)0.0513 (14)0.0462 (14)0.0064 (11)−0.0047 (10)0.0040 (12)
C80.0407 (14)0.0651 (17)0.0679 (17)0.0015 (13)−0.0041 (12)0.0126 (14)
C90.0388 (13)0.0586 (16)0.0562 (15)−0.0020 (12)−0.0018 (11)0.0095 (12)
C100.0429 (13)0.0609 (16)0.0510 (15)−0.0045 (13)−0.0015 (11)0.0036 (13)
C110.0379 (13)0.0557 (15)0.0512 (15)−0.0006 (11)0.0068 (11)0.0065 (12)
C120.0309 (12)0.0614 (16)0.0536 (15)−0.0005 (12)0.0056 (11)0.0088 (12)
C130.0375 (13)0.0700 (17)0.0497 (15)−0.0021 (12)0.0020 (11)0.0026 (13)
C140.0413 (14)0.0644 (17)0.0612 (17)0.0033 (12)0.0051 (12)−0.0020 (13)
C150.0501 (16)0.113 (2)0.0569 (18)0.0101 (17)−0.0042 (13)−0.0163 (17)
C160.106 (3)0.208 (5)0.105 (3)0.055 (3)−0.034 (2)−0.092 (3)
C170.072 (2)0.217 (5)0.058 (2)−0.007 (3)−0.0067 (17)0.031 (3)
C180.070 (2)0.128 (3)0.090 (2)−0.016 (2)−0.0125 (17)−0.031 (2)
C190.0473 (15)0.0646 (17)0.0616 (17)0.0025 (13)0.0091 (12)−0.0025 (14)
C200.084 (2)0.091 (2)0.071 (2)0.0077 (18)0.0033 (17)−0.0192 (18)
C210.0661 (19)0.102 (3)0.086 (2)−0.0117 (18)0.0308 (16)−0.0162 (19)
C220.079 (2)0.069 (2)0.099 (2)0.0095 (17)0.0052 (18)0.0039 (18)
C230.154 (4)0.123 (3)0.138 (4)0.040 (3)−0.021 (3)−0.026 (3)
C240.081 (3)0.181 (5)0.116 (3)0.021 (3)−0.007 (2)−0.011 (3)
C250.071 (2)0.099 (3)0.099 (3)0.0172 (19)−0.0035 (19)0.003 (2)
C260.0496 (17)0.098 (2)0.084 (2)0.0130 (17)−0.0005 (15)0.0249 (19)
C270.0577 (18)0.088 (2)0.089 (2)−0.0107 (17)−0.0169 (16)0.0154 (18)
C280.069 (2)0.095 (3)0.107 (3)−0.0073 (19)−0.0078 (19)−0.009 (2)
C290.090 (3)0.130 (3)0.117 (3)−0.010 (2)−0.009 (2)−0.021 (3)
C300.105 (3)0.183 (5)0.147 (4)−0.021 (3)0.022 (3)−0.055 (4)

Geometric parameters (Å, °)

C1—O21.235 (3)C17—H17B0.9600
C1—O11.235 (3)C17—H17C0.9600
C1—C21.500 (3)C18—H18A0.9600
S1—C71.767 (2)C18—H18B0.9600
S1—C81.816 (2)C18—H18C0.9600
O3—C121.385 (3)C19—C221.529 (4)
O3—H30.806 (18)C19—C211.534 (4)
N1—C261.474 (4)C19—C201.538 (4)
N1—C271.476 (4)C20—H20A0.9600
N1—H1A0.890 (17)C20—H20B0.9600
N1—H1B0.892 (17)C20—H20C0.9600
C2—C31.387 (3)C21—H21A0.9600
C2—C71.409 (3)C21—H21B0.9600
C3—C41.364 (4)C21—H21C0.9600
C3—H3A0.9300C22—H22A0.9600
C4—C51.366 (4)C22—H22B0.9600
C4—H40.9300C22—H22C0.9600
C5—C61.383 (3)C23—C241.450 (5)
C5—H50.9300C23—H23A0.9600
C6—C71.389 (3)C23—H23B0.9600
C6—H60.9300C23—H23C0.9600
C8—C91.504 (3)C24—C251.513 (5)
C8—H8A0.9700C24—H24A0.9700
C8—H8B0.9700C24—H24B0.9700
C9—C101.374 (3)C25—C261.499 (4)
C9—C141.379 (3)C25—H25A0.9700
C10—C111.393 (3)C25—H25B0.9700
C10—H100.9300C26—H26A0.9700
C11—C121.400 (3)C26—H26B0.9700
C11—C191.543 (3)C27—C281.521 (4)
C12—C131.405 (3)C27—H27A0.9700
C13—C141.392 (3)C27—H27B0.9700
C13—C151.538 (4)C28—C291.490 (5)
C14—H140.9300C28—H28A0.9700
C15—C171.526 (5)C28—H28B0.9700
C15—C181.532 (4)C29—C301.498 (5)
C15—C161.538 (4)C29—H29A0.9700
C16—H16A0.9600C29—H29B0.9700
C16—H16B0.9600C30—H30A0.9600
C16—H16C0.9600C30—H30B0.9600
C17—H17A0.9600C30—H30C0.9600
O2—C1—O1122.1 (3)H18A—C18—H18C109.5
O2—C1—C2119.5 (2)H18B—C18—H18C109.5
O1—C1—C2118.4 (2)C22—C19—C21110.4 (2)
C7—S1—C8103.55 (11)C22—C19—C20107.2 (2)
C12—O3—H3114 (3)C21—C19—C20106.7 (2)
C26—N1—C27114.0 (2)C22—C19—C11111.4 (2)
C26—N1—H1A109.4 (18)C21—C19—C11109.5 (2)
C27—N1—H1A108.8 (18)C20—C19—C11111.5 (2)
C26—N1—H1B107.3 (18)C19—C20—H20A109.5
C27—N1—H1B106.9 (18)C19—C20—H20B109.5
H1A—N1—H1B110 (3)H20A—C20—H20B109.5
C3—C2—C7118.5 (2)C19—C20—H20C109.5
C3—C2—C1118.1 (2)H20A—C20—H20C109.5
C7—C2—C1123.4 (2)H20B—C20—H20C109.5
C4—C3—C2122.5 (2)C19—C21—H21A109.5
C4—C3—H3A118.8C19—C21—H21B109.5
C2—C3—H3A118.8H21A—C21—H21B109.5
C3—C4—C5119.2 (2)C19—C21—H21C109.5
C3—C4—H4120.4H21A—C21—H21C109.5
C5—C4—H4120.4H21B—C21—H21C109.5
C4—C5—C6120.2 (3)C19—C22—H22A109.5
C4—C5—H5119.9C19—C22—H22B109.5
C6—C5—H5119.9H22A—C22—H22B109.5
C5—C6—C7121.3 (2)C19—C22—H22C109.5
C5—C6—H6119.4H22A—C22—H22C109.5
C7—C6—H6119.4H22B—C22—H22C109.5
C6—C7—C2118.3 (2)C24—C23—H23A109.5
C6—C7—S1120.62 (18)C24—C23—H23B109.5
C2—C7—S1121.05 (17)H23A—C23—H23B109.5
C9—C8—S1107.30 (17)C24—C23—H23C109.5
C9—C8—H8A110.3H23A—C23—H23C109.5
S1—C8—H8A110.3H23B—C23—H23C109.5
C9—C8—H8B110.3C23—C24—C25116.3 (4)
S1—C8—H8B110.3C23—C24—H24A108.2
H8A—C8—H8B108.5C25—C24—H24A108.2
C10—C9—C14118.3 (2)C23—C24—H24B108.2
C10—C9—C8121.6 (2)C25—C24—H24B108.2
C14—C9—C8120.1 (2)H24A—C24—H24B107.4
C9—C10—C11122.7 (2)C26—C25—C24112.1 (3)
C9—C10—H10118.6C26—C25—H25A109.2
C11—C10—H10118.6C24—C25—H25A109.2
C10—C11—C12117.1 (2)C26—C25—H25B109.2
C10—C11—C19120.4 (2)C24—C25—H25B109.2
C12—C11—C19122.5 (2)H25A—C25—H25B107.9
O3—C12—C11118.8 (2)N1—C26—C25112.2 (2)
O3—C12—C13118.9 (2)N1—C26—H26A109.2
C11—C12—C13122.2 (2)C25—C26—H26A109.2
C14—C13—C12117.0 (2)N1—C26—H26B109.2
C14—C13—C15120.0 (2)C25—C26—H26B109.2
C12—C13—C15122.9 (2)H26A—C26—H26B107.9
C9—C14—C13122.7 (2)N1—C27—C28111.4 (2)
C9—C14—H14118.7N1—C27—H27A109.3
C13—C14—H14118.7C28—C27—H27A109.3
C17—C15—C18110.2 (3)N1—C27—H27B109.3
C17—C15—C13109.0 (3)C28—C27—H27B109.3
C18—C15—C13112.2 (2)H27A—C27—H27B108.0
C17—C15—C16107.4 (3)C29—C28—C27113.0 (3)
C18—C15—C16106.9 (3)C29—C28—H28A109.0
C13—C15—C16111.0 (2)C27—C28—H28A109.0
C15—C16—H16A109.5C29—C28—H28B109.0
C15—C16—H16B109.5C27—C28—H28B109.0
H16A—C16—H16B109.5H28A—C28—H28B107.8
C15—C16—H16C109.5C28—C29—C30113.4 (3)
H16A—C16—H16C109.5C28—C29—H29A108.9
H16B—C16—H16C109.5C30—C29—H29A108.9
C15—C17—H17A109.5C28—C29—H29B108.9
C15—C17—H17B109.5C30—C29—H29B108.9
H17A—C17—H17B109.5H29A—C29—H29B107.7
C15—C17—H17C109.5C29—C30—H30A109.5
H17A—C17—H17C109.5C29—C30—H30B109.5
H17B—C17—H17C109.5H30A—C30—H30B109.5
C15—C18—H18A109.5C29—C30—H30C109.5
C15—C18—H18B109.5H30A—C30—H30C109.5
H18A—C18—H18B109.5H30B—C30—H30C109.5
C15—C18—H18C109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···O1i0.81 (2)2.02 (2)2.723 (3)146 (3)
N1—H1A···O20.89 (2)1.88 (2)2.767 (3)177 (3)
N1—H1B···O1ii0.89 (2)2.00 (2)2.806 (3)150 (3)
N1—H1B···O2ii0.89 (2)2.36 (2)3.167 (3)150 (2)
N1—H1B···O2ii0.89 (2)2.36 (2)3.167 (3)150 (2)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2302).

References

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  • Mansor, S., Yehye, W. A., Ariffin, A., Rahman, N. A. & Ng, S. W. (2008). Acta Cryst. E64, o1799. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
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