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ISSN: 2056-9890

2-[2-(3-Methyl­but­­oxy)-5-nitro­benz­amido]­acetic acid di­methyl sulfoxide monosolvate

aKey Laboratory of Polymer Materials of Gansu Province Ministry of Education, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, Gansu, People's Republic of China, bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and cChemistry Department, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
*Correspondence e-mail: seikweng@um.edu.my

(Received 15 June 2012; accepted 16 June 2012; online 23 June 2012)

In the title compound, C14H18N2O6·C2H6OS, the –C(O)NHCH2CO2H and –O(CH2)2CH(CH3)2 substitutents of the aromatic ring are positioned such that the –NH– group is hydrogen-bond donor to the ether O atom of the other substituent. The dimethyl sulfoxide solvent mol­ecule is linked to the carb­oxy­lic acid group by an O—H⋯O hydrogen bond.

Related literature

For background to this study, see: Shaginian et al. (2009[Shaginian, A., Whitby, L. R., Hong, S., Hwang, I., Farooqi, B., Searcey, M., Chen, J., Vogt, P. K. & Boger, D. L. (2009). J. Am. Chem. Soc. 131, 5564-5572.]).

[Scheme 1]

Experimental

Crystal data
  • C14H18N2O6·C2H6OS

  • Mr = 388.43

  • Triclinic, [P \overline 1]

  • a = 7.4603 (12) Å

  • b = 11.2881 (18) Å

  • c = 11.5861 (19) Å

  • α = 99.229 (3)°

  • β = 99.802 (3)°

  • γ = 93.487 (3)°

  • V = 945.1 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.21 mm−1

  • T = 293 K

  • 0.27 × 0.24 × 0.18 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.945, Tmax = 0.963

  • 5211 measured reflections

  • 3644 independent reflections

  • 2558 reflections with I > 2σ(I)

  • Rint = 0.035

Refinement
  • R[F2 > 2σ(F2)] = 0.057

  • wR(F2) = 0.144

  • S = 1.01

  • 3644 reflections

  • 243 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯O7 0.84 (1) 1.75 (1) 2.579 (3) 170 (3)
N1—H2⋯O4 0.87 (1) 1.97 (2) 2.656 (3) 135 (2)

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

The title compound is one that is similar to those identified for a study of protein-protein interactions (Shaginian et al., 2009). It crystallizes from DMSO as a monosolvate (Scheme I, Fig. 1). The –C(O)NHCH2CO2H and –O(CH2)2CH(CH3)2 substitutents of the aromatic ring of C14H18N2O6.DMSO are positioned such that the –NH– group is hydrogen-bond donor to the ether O of the other substituent. The solvent molecule is linked to the carboxylic acid by an O–H···O hydrogen bond (Table 1).

Related literature top

For background to this study, see: Shaginian et al. (2009).

Experimental top

2-(Isopentyloxy)-4-nitrobenzoic acid (0.51 g, 2 mmol) was dissolved in thionyl chloride (2 ml). The synthesis is based on that reported for 2-methoxy-4-nitrobenzoic acid. The mixture was heated for half an hour. The excess reactant was evaporated and the residue dissolved in dichloromethane (10 ml) for the subsequent coupling reaction.

To a solution of methyl 2-aminoacetate hydrochloride (0.26 g, 2.1 mmol) in dichloromethane (30 ml) and triethylamine (0.5 ml) was added the above acid chloride at 273 K. The mixture was stirred at room temperature for half an hour. The solvent was removed and the residue was dissolved in methanol (50 ml) containing lithium hydroxide hydrate (0.65 g, 10 mmol) dissolved in water (2 ml). The mixture was heated for 5 h. The residue after removal of most of the solvent was acidified with 10% hydrochloric acid to a pH of 3. Filtration afforded the product as a white solid (0.41 g, 70%). Crystals were grown in DMSO.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C–H 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.20 to 1.5U(C).

The acid and amino H-atoms were located in a difference Fourier map, and were refined with distance restrainst of O–H 0.84±0.01 and N–H 0.84±0.01 Å; their temperature factors were freely refined.

Structure description top

The title compound is one that is similar to those identified for a study of protein-protein interactions (Shaginian et al., 2009). It crystallizes from DMSO as a monosolvate (Scheme I, Fig. 1). The –C(O)NHCH2CO2H and –O(CH2)2CH(CH3)2 substitutents of the aromatic ring of C14H18N2O6.DMSO are positioned such that the –NH– group is hydrogen-bond donor to the ether O of the other substituent. The solvent molecule is linked to the carboxylic acid by an O–H···O hydrogen bond (Table 1).

For background to this study, see: Shaginian et al. (2009).

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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C14H18N2O6.DMSO at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
2-[2-(3-Methylbutoxy)-5-nitrobenzamido]acetic acid dimethyl sulfoxide monosolvate top
Crystal data top
C14H18N2O6·C2H6OSZ = 2
Mr = 388.43F(000) = 412
Triclinic, P1Dx = 1.365 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4603 (12) ÅCell parameters from 3644 reflections
b = 11.2881 (18) Åθ = 1.8–26.0°
c = 11.5861 (19) ŵ = 0.21 mm1
α = 99.229 (3)°T = 293 K
β = 99.802 (3)°Prism, colorless
γ = 93.487 (3)°0.27 × 0.24 × 0.18 mm
V = 945.1 (3) Å3
Data collection top
Bruker SMART APEX
diffractometer
3644 independent reflections
Radiation source: fine-focus sealed tube2558 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
ω scansθmax = 26.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 89
Tmin = 0.945, Tmax = 0.963k = 1213
5211 measured reflectionsl = 1314
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0647P)2]
where P = (Fo2 + 2Fc2)/3
3644 reflections(Δ/σ)max = 0.001
243 parametersΔρmax = 0.32 e Å3
2 restraintsΔρmin = 0.29 e Å3
Crystal data top
C14H18N2O6·C2H6OSγ = 93.487 (3)°
Mr = 388.43V = 945.1 (3) Å3
Triclinic, P1Z = 2
a = 7.4603 (12) ÅMo Kα radiation
b = 11.2881 (18) ŵ = 0.21 mm1
c = 11.5861 (19) ÅT = 293 K
α = 99.229 (3)°0.27 × 0.24 × 0.18 mm
β = 99.802 (3)°
Data collection top
Bruker SMART APEX
diffractometer
3644 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2558 reflections with I > 2σ(I)
Tmin = 0.945, Tmax = 0.963Rint = 0.035
5211 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0572 restraints
wR(F2) = 0.144H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.32 e Å3
3644 reflectionsΔρmin = 0.29 e Å3
243 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.28957 (10)0.17297 (6)0.17669 (6)0.0234 (2)
O10.2603 (3)0.00955 (17)0.47071 (18)0.0255 (5)
O20.2747 (3)0.14280 (17)0.36944 (18)0.0370 (6)
O30.1140 (3)0.36605 (17)0.72134 (17)0.0262 (5)
O40.2827 (2)0.47573 (16)0.42855 (15)0.0181 (4)
O50.1885 (3)0.92011 (17)0.80371 (18)0.0297 (5)
O60.0932 (3)0.77455 (18)0.88517 (17)0.0295 (5)
O70.3687 (3)0.15722 (17)0.30829 (17)0.0271 (5)
N10.2100 (3)0.3040 (2)0.5503 (2)0.0187 (5)
N20.1524 (3)0.8122 (2)0.8040 (2)0.0222 (6)
C10.2487 (4)0.1034 (2)0.4564 (2)0.0208 (6)
C20.1965 (4)0.1786 (2)0.5629 (2)0.0194 (6)
H2A0.07250.15330.56920.023*
H2B0.27720.16790.63470.023*
C30.1688 (4)0.3899 (2)0.6327 (2)0.0167 (6)
C40.1942 (3)0.5189 (2)0.6155 (2)0.0153 (6)
C50.2520 (3)0.5602 (2)0.5177 (2)0.0155 (6)
C60.2746 (4)0.6832 (2)0.5155 (2)0.0191 (6)
H60.31130.70950.45040.023*
C70.2429 (4)0.7664 (2)0.6094 (2)0.0192 (6)
H70.26030.84860.60890.023*
C80.1850 (4)0.7253 (2)0.7040 (2)0.0181 (6)
C90.1608 (3)0.6042 (2)0.7080 (2)0.0153 (6)
H90.12170.57940.77310.018*
C100.3186 (4)0.5110 (2)0.3185 (2)0.0181 (6)
H10A0.43030.56410.33340.022*
H10B0.21870.55240.28320.022*
C110.3368 (4)0.3956 (2)0.2372 (2)0.0182 (6)
H11A0.22460.34350.22530.022*
H11B0.43460.35470.27570.022*
C120.3764 (4)0.4145 (3)0.1161 (2)0.0232 (7)
H120.48640.47050.12890.028*
C130.4120 (4)0.2954 (3)0.0449 (3)0.0322 (8)
H13A0.43780.30840.03070.048*
H13B0.30610.23910.03280.048*
H13C0.51460.26370.08780.048*
C140.2198 (4)0.4682 (3)0.0460 (3)0.0283 (7)
H14A0.19780.54320.09120.043*
H14B0.11170.41330.03070.043*
H14C0.25110.48200.02800.043*
C150.3742 (5)0.0420 (3)0.1283 (3)0.0330 (8)
H15A0.50240.04470.12760.049*
H15B0.35520.02860.18160.049*
H15C0.31050.03930.04960.049*
C160.0586 (4)0.1409 (3)0.1671 (3)0.0285 (7)
H16A0.00980.20460.19100.043*
H16B0.00830.13450.08660.043*
H16C0.05200.06620.21850.043*
H10.295 (4)0.051 (2)0.4133 (19)0.035 (10)*
H20.242 (4)0.323 (2)0.4863 (16)0.027 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0284 (4)0.0195 (4)0.0233 (4)0.0026 (3)0.0109 (3)0.0000 (3)
O10.0410 (14)0.0135 (11)0.0255 (12)0.0049 (10)0.0135 (10)0.0049 (9)
O20.0716 (18)0.0176 (12)0.0282 (12)0.0052 (11)0.0252 (12)0.0055 (9)
O30.0385 (13)0.0217 (11)0.0219 (11)0.0012 (10)0.0145 (10)0.0051 (9)
O40.0240 (11)0.0174 (10)0.0149 (10)0.0030 (8)0.0083 (8)0.0034 (8)
O50.0378 (13)0.0145 (11)0.0364 (13)0.0038 (10)0.0104 (10)0.0012 (9)
O60.0344 (13)0.0317 (13)0.0230 (12)0.0004 (10)0.0142 (10)0.0013 (9)
O70.0350 (13)0.0226 (12)0.0238 (11)0.0060 (10)0.0064 (9)0.0019 (9)
N10.0255 (14)0.0140 (12)0.0190 (13)0.0003 (10)0.0092 (11)0.0049 (10)
N20.0197 (13)0.0208 (14)0.0245 (14)0.0040 (11)0.0047 (11)0.0023 (11)
C10.0210 (16)0.0204 (16)0.0208 (16)0.0004 (13)0.0026 (12)0.0053 (13)
C20.0232 (16)0.0152 (15)0.0209 (15)0.0016 (12)0.0066 (12)0.0053 (12)
C30.0160 (14)0.0173 (15)0.0169 (14)0.0025 (12)0.0028 (11)0.0032 (12)
C40.0121 (14)0.0172 (15)0.0162 (14)0.0019 (11)0.0004 (11)0.0033 (11)
C50.0106 (14)0.0202 (15)0.0145 (14)0.0019 (11)0.0003 (11)0.0016 (11)
C60.0186 (15)0.0209 (16)0.0182 (15)0.0006 (12)0.0022 (12)0.0066 (12)
C70.0216 (16)0.0126 (14)0.0243 (16)0.0041 (12)0.0038 (12)0.0055 (12)
C80.0163 (15)0.0199 (15)0.0169 (15)0.0025 (12)0.0026 (11)0.0004 (12)
C90.0100 (13)0.0210 (15)0.0154 (14)0.0018 (11)0.0027 (11)0.0046 (11)
C100.0210 (15)0.0214 (15)0.0130 (14)0.0017 (12)0.0055 (11)0.0040 (11)
C110.0153 (15)0.0195 (15)0.0206 (15)0.0020 (12)0.0040 (11)0.0053 (12)
C120.0207 (16)0.0300 (18)0.0195 (16)0.0003 (13)0.0075 (12)0.0029 (13)
C130.0303 (18)0.045 (2)0.0211 (16)0.0127 (16)0.0077 (14)0.0016 (14)
C140.0378 (19)0.0287 (18)0.0197 (16)0.0055 (15)0.0064 (14)0.0058 (13)
C150.039 (2)0.0322 (19)0.0277 (18)0.0078 (16)0.0114 (15)0.0055 (14)
C160.0275 (18)0.0353 (19)0.0238 (16)0.0034 (14)0.0088 (13)0.0041 (14)
Geometric parameters (Å, º) top
S1—O71.516 (2)C7—H70.9300
S1—C161.771 (3)C8—C91.378 (4)
S1—C151.781 (3)C9—H90.9300
O1—C11.317 (3)C10—C111.507 (4)
O1—H10.838 (10)C10—H10A0.9700
O2—C11.205 (3)C10—H10B0.9700
O3—C31.230 (3)C11—C121.526 (4)
O4—C51.348 (3)C11—H11A0.9700
O4—C101.457 (3)C11—H11B0.9700
O5—N21.232 (3)C12—C141.521 (4)
O6—N21.228 (3)C12—C131.524 (4)
N1—C31.336 (3)C12—H120.9800
N1—C21.445 (3)C13—H13A0.9600
N1—H20.873 (10)C13—H13B0.9600
N2—C81.457 (3)C13—H13C0.9600
C1—C21.504 (4)C14—H14A0.9600
C2—H2A0.9700C14—H14B0.9600
C2—H2B0.9700C14—H14C0.9600
C3—C41.505 (4)C15—H15A0.9600
C4—C91.389 (3)C15—H15B0.9600
C4—C51.414 (3)C15—H15C0.9600
C5—C61.394 (4)C16—H16A0.9600
C6—C71.381 (4)C16—H16B0.9600
C6—H60.9300C16—H16C0.9600
C7—C81.379 (4)
O7—S1—C16106.07 (13)O4—C10—H10A110.6
O7—S1—C15105.75 (13)C11—C10—H10A110.6
C16—S1—C1598.07 (15)O4—C10—H10B110.6
C1—O1—H1112 (2)C11—C10—H10B110.6
C5—O4—C10119.82 (19)H10A—C10—H10B108.7
C3—N1—C2121.4 (2)C10—C11—C12113.6 (2)
C3—N1—H2119.6 (19)C10—C11—H11A108.8
C2—N1—H2119.0 (19)C12—C11—H11A108.8
O6—N2—O5123.2 (2)C10—C11—H11B108.8
O6—N2—C8118.6 (2)C12—C11—H11B108.8
O5—N2—C8118.2 (2)H11A—C11—H11B107.7
O2—C1—O1125.2 (3)C14—C12—C13109.7 (2)
O2—C1—C2123.4 (2)C14—C12—C11111.6 (2)
O1—C1—C2111.4 (2)C13—C12—C11110.1 (2)
N1—C2—C1109.4 (2)C14—C12—H12108.4
N1—C2—H2A109.8C13—C12—H12108.4
C1—C2—H2A109.8C11—C12—H12108.4
N1—C2—H2B109.8C12—C13—H13A109.5
C1—C2—H2B109.8C12—C13—H13B109.5
H2A—C2—H2B108.2H13A—C13—H13B109.5
O3—C3—N1121.8 (2)C12—C13—H13C109.5
O3—C3—C4120.2 (2)H13A—C13—H13C109.5
N1—C3—C4118.1 (2)H13B—C13—H13C109.5
C9—C4—C5118.1 (2)C12—C14—H14A109.5
C9—C4—C3115.2 (2)C12—C14—H14B109.5
C5—C4—C3126.7 (2)H14A—C14—H14B109.5
O4—C5—C6122.6 (2)C12—C14—H14C109.5
O4—C5—C4117.1 (2)H14A—C14—H14C109.5
C6—C5—C4120.3 (2)H14B—C14—H14C109.5
C7—C6—C5120.5 (2)S1—C15—H15A109.5
C7—C6—H6119.7S1—C15—H15B109.5
C5—C6—H6119.7H15A—C15—H15B109.5
C8—C7—C6118.8 (2)S1—C15—H15C109.5
C8—C7—H7120.6H15A—C15—H15C109.5
C6—C7—H7120.6H15B—C15—H15C109.5
C9—C8—C7121.9 (2)S1—C16—H16A109.5
C9—C8—N2118.8 (2)S1—C16—H16B109.5
C7—C8—N2119.3 (2)H16A—C16—H16B109.5
C8—C9—C4120.4 (2)S1—C16—H16C109.5
C8—C9—H9119.8H16A—C16—H16C109.5
C4—C9—H9119.8H16B—C16—H16C109.5
O4—C10—C11105.9 (2)
C3—N1—C2—C1179.2 (2)C4—C5—C6—C70.8 (4)
O2—C1—C2—N18.4 (4)C5—C6—C7—C81.3 (4)
O1—C1—C2—N1172.2 (2)C6—C7—C8—C91.0 (4)
C2—N1—C3—O31.5 (4)C6—C7—C8—N2179.6 (2)
C2—N1—C3—C4177.4 (2)O6—N2—C8—C94.5 (4)
O3—C3—C4—C93.1 (4)O5—N2—C8—C9174.3 (2)
N1—C3—C4—C9175.9 (2)O6—N2—C8—C7176.8 (3)
O3—C3—C4—C5178.5 (3)O5—N2—C8—C74.3 (4)
N1—C3—C4—C52.5 (4)C7—C8—C9—C40.1 (4)
C10—O4—C5—C68.0 (4)N2—C8—C9—C4178.7 (2)
C10—O4—C5—C4171.8 (2)C5—C4—C9—C80.5 (4)
C9—C4—C5—O4179.6 (2)C3—C4—C9—C8178.0 (2)
C3—C4—C5—O42.1 (4)C5—O4—C10—C11177.2 (2)
C9—C4—C5—C60.2 (4)O4—C10—C11—C12179.6 (2)
C3—C4—C5—C6178.1 (3)C10—C11—C12—C1463.7 (3)
O4—C5—C6—C7179.5 (2)C10—C11—C12—C13174.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O70.84 (1)1.75 (1)2.579 (3)170 (3)
N1—H2···O40.87 (1)1.97 (2)2.656 (3)135 (2)

Experimental details

Crystal data
Chemical formulaC14H18N2O6·C2H6OS
Mr388.43
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.4603 (12), 11.2881 (18), 11.5861 (19)
α, β, γ (°)99.229 (3), 99.802 (3), 93.487 (3)
V3)945.1 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.21
Crystal size (mm)0.27 × 0.24 × 0.18
Data collection
DiffractometerBruker SMART APEX
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.945, 0.963
No. of measured, independent and
observed [I > 2σ(I)] reflections
5211, 3644, 2558
Rint0.035
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.144, 1.01
No. of reflections3644
No. of parameters243
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.32, 0.29

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O70.84 (1)1.75 (1)2.579 (3)170 (3)
N1—H2···O40.87 (1)1.97 (2)2.656 (3)135 (2)
 

Acknowledgements

We thank Northeast Normal University and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12) for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationShaginian, A., Whitby, L. R., Hong, S., Hwang, I., Farooqi, B., Searcey, M., Chen, J., Vogt, P. K. & Boger, D. L. (2009). J. Am. Chem. Soc. 131, 5564–5572.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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