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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2842.
Published online 2010 October 20. doi:  10.1107/S1600536810040316
PMCID: PMC3008974

1-Allyl-4-(1,3-benzothia­zol-2-yl)-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one

Abstract

The title compound, C20H17N3OS, is a 1H-pyrazol-3(2H)-one having aromatic 4-(1,3-benzothia­zol-2-yl)- and 2-phenyl substituents. The five-membered ring and fused ring system are planar, the r.m.s. deviations being 0.021 and 0.005 Å, respectively. The five-membered ring is aligned at 7.9 (2)° with respect to the fused-ring system. The allyl and phenyl parts of the mol­ecule are both disordered over two positions in a 1:1 ratio. Weak inter­molecular C—H(...)O hydrogen bonding is present in the crystal structure.

Related literature

For the structure of a related compound (E)-4-(2,3-dihydro-1,3-benzothia­zol-2-yl­idene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one, see: Chakibe et al. (2010 [triangle]).

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Object name is e-66-o2842-scheme1.jpg

Experimental

Crystal data

  • C20H17N3OS
  • M r = 347.43
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2842-efi1.jpg
  • a = 17.8734 (5) Å
  • b = 10.4297 (2) Å
  • c = 18.9578 (4) Å
  • V = 3534.00 (14) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.20 mm−1
  • T = 293 K
  • 0.30 × 0.30 × 0.25 mm

Data collection

  • Bruker X8 APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.944, T max = 0.953
  • 18349 measured reflections
  • 3678 independent reflections
  • 2341 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.172
  • S = 1.00
  • 3678 reflections
  • 227 parameters
  • 17 restraints
  • H-atom parameters constrained
  • Δρmax = 0.32 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810040316/xu5047sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040316/xu5047Isup2.hkl

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

Acknowledgments

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

(E)-4-(2,3-Dihydro-1,3-benzothiazol-2-ylidene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one is an amine that can under a nucleophilic substitution with organo bromides to form 2-substituted derivatives if tetra-n-butyl ammonium bromide is used as catalyst. In this study, the compound is reacted with allyl bromide to yield the title compound (Scheme I, Fig. 1).

Experimental

To a solution of (E)-4-(2,3-dihydro-1,3-benzothiazol-2-ylidene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one (1 g, 3.25 mmol) in DMF (50 ml), was added sodium carbonate (2.5 g, 23 mmol), tetra-n-butyl ammonium bromide (0.15 g, 1 mmol) and allyl bromide (5.6 g, 46 mmol). The mixture was stirred for 24 h at room temperature. The solid material was removed by filtration and the solution was evaporated under reduced. The residue was washed with dichloromethane and hexane, and the recrystallized from ethanol to afford the title compound as colorless crystals.

Refinement

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 1.2–1.5Ueq(C).

The allyl and phenyl units are disordered over two positions; the disorder could be refined, and was assumed to be a 1:1 type of disorder. For the allyl unit, the single-bond distances were restrained to 1.50±0.01 Å and the double-bond distances to 1.35±0.01 Å; the anisotropic temperature factors were restrained to be nearly isotropic. The phenyl rings were refined as rigid hexagons of 1.39 Å sides; the N–Cphenyl pair of distances were restrained to within 0.01 Å of each other. Additionally, the temperature factors of the primed atoms were restrained to those of the unprimed ones.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C20H17N3OS at the 50% probability level; hydrogen atoms are drawn as arbitrary radius. The disorder is not shown

Crystal data

C20H17N3OSF(000) = 1456
Mr = 347.43Dx = 1.306 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3745 reflections
a = 17.8734 (5) Åθ = 2.3–22.5°
b = 10.4297 (2) ŵ = 0.20 mm1
c = 18.9578 (4) ÅT = 293 K
V = 3534.00 (14) Å3Prism, colorless
Z = 80.30 × 0.30 × 0.25 mm

Data collection

Bruker X8 APEXII diffractometer3678 independent reflections
Radiation source: fine-focus sealed tube2341 reflections with I > 2σ(I)
graphiteRint = 0.032
[var phi] and ω scansθmax = 26.6°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −22→21
Tmin = 0.944, Tmax = 0.953k = −13→12
18349 measured reflectionsl = −23→23

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) = 0.172H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.096P)2 + 0.8646P] where P = (Fo2 + 2Fc2)/3
3678 reflections(Δ/σ)max = 0.001
227 parametersΔρmax = 0.32 e Å3
17 restraintsΔρmin = −0.25 e Å3

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

xyzUiso*/UeqOcc. (<1)
S10.54022 (4)0.59623 (7)0.57529 (3)0.0590 (2)
O10.63189 (12)0.5096 (2)0.45761 (10)0.0808 (6)
N10.61613 (12)0.7853 (2)0.62953 (11)0.0590 (6)
N20.79529 (13)0.6762 (2)0.48741 (11)0.0593 (6)
N30.75432 (13)0.5809 (2)0.45335 (11)0.0627 (6)
C10.50073 (15)0.6812 (2)0.64448 (12)0.0531 (6)
C20.43115 (17)0.6640 (3)0.67650 (14)0.0669 (7)
H20.39890.59950.66170.080*
C30.41164 (19)0.7448 (3)0.73035 (15)0.0762 (9)
H30.36540.73490.75220.091*
C40.4595 (2)0.8412 (3)0.75287 (16)0.0798 (9)
H40.44540.89430.79000.096*
C50.52717 (19)0.8589 (3)0.72110 (15)0.0743 (8)
H50.55870.92420.73620.089*
C60.54904 (16)0.7785 (2)0.66569 (12)0.0566 (6)
C70.61898 (14)0.6956 (2)0.58142 (11)0.0495 (6)
C80.68208 (17)0.5800 (3)0.48056 (13)0.0603 (7)
C90.68293 (15)0.6721 (2)0.53608 (12)0.0518 (6)
C100.75276 (15)0.7255 (2)0.53898 (12)0.0548 (6)
C110.78327 (19)0.8222 (3)0.58934 (16)0.0760 (8)
H11A0.82690.86170.56930.114*
H11B0.79650.78060.63270.114*
H11C0.74610.88650.59840.114*
C120.87637 (17)0.6862 (3)0.48056 (16)0.0746 (8)
H12A0.89140.77550.48060.090*0.50
H12B0.89260.64750.43660.090*0.50
H12C0.88250.77820.48520.090*0.50
H12D0.88120.67080.43030.090*0.50
C130.9121 (11)0.6151 (15)0.5440 (7)0.101 (3)0.50
H130.89150.53980.56160.121*0.50
C140.9722 (11)0.6652 (18)0.5718 (9)0.139 (4)0.50
H14A0.99200.74070.55350.166*0.50
H14B0.99530.62540.60990.166*0.50
C13'0.9175 (11)0.5938 (15)0.5294 (7)0.101 (3)0.50
H13'0.91480.50760.51710.121*0.50
C14'0.9555 (11)0.6196 (18)0.5854 (8)0.139 (4)0.50
H14C0.96030.70410.60040.166*0.50
H14D0.97810.55380.61070.166*0.50
C150.7691 (10)0.5140 (10)0.3885 (4)0.0510 (18)0.50
C160.8277 (10)0.4304 (14)0.3741 (5)0.0863 (18)0.50
H160.85610.39690.41080.104*0.50
C170.8437 (10)0.3967 (13)0.3048 (5)0.105 (3)0.50
H170.88290.34070.29510.126*0.50
C180.8012 (11)0.4466 (10)0.2499 (4)0.110 (4)0.50
H180.81190.42410.20350.132*0.50
C190.7426 (10)0.5303 (12)0.2643 (6)0.102 (3)0.50
H190.71420.56370.22750.123*0.50
C200.7265 (9)0.5640 (12)0.3336 (7)0.0714 (19)0.50
H200.68740.61990.34320.086*0.50
C15'0.7791 (10)0.5424 (10)0.3848 (5)0.0510 (18)0.50
C16'0.8326 (10)0.4458 (14)0.3884 (4)0.0863 (18)0.50
H16'0.85710.42940.43080.104*0.50
C17'0.8494 (11)0.3738 (12)0.3288 (5)0.105 (3)0.50
H17'0.88520.30920.33120.126*0.50
C18'0.8127 (11)0.3984 (9)0.2656 (4)0.110 (4)0.50
H18'0.82400.35020.22570.132*0.50
C19'0.7593 (10)0.4949 (13)0.2620 (5)0.102 (3)0.50
H19'0.73470.51130.21970.123*0.50
C20'0.7425 (9)0.5669 (11)0.3216 (7)0.0714 (19)0.50
H20'0.70670.63150.31920.086*0.50

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0542 (4)0.0698 (4)0.0528 (4)−0.0033 (3)0.0062 (3)−0.0106 (3)
O10.0647 (13)0.1020 (15)0.0756 (13)−0.0228 (12)0.0166 (10)−0.0337 (12)
N10.0559 (14)0.0630 (12)0.0580 (12)0.0042 (10)0.0020 (10)−0.0066 (10)
N20.0529 (14)0.0655 (12)0.0594 (12)−0.0072 (11)0.0080 (10)−0.0040 (10)
N30.0568 (14)0.0740 (13)0.0573 (12)−0.0097 (11)0.0118 (11)−0.0143 (10)
C10.0521 (16)0.0634 (14)0.0438 (12)0.0102 (12)−0.0007 (11)0.0048 (10)
C20.0615 (18)0.0812 (18)0.0581 (15)0.0026 (15)0.0106 (13)0.0007 (13)
C30.067 (2)0.100 (2)0.0611 (16)0.0151 (18)0.0163 (15)0.0006 (15)
C40.084 (2)0.090 (2)0.0657 (17)0.0216 (19)0.0131 (17)−0.0169 (16)
C50.075 (2)0.0803 (18)0.0677 (17)0.0077 (16)0.0047 (16)−0.0213 (15)
C60.0589 (17)0.0610 (14)0.0500 (13)0.0111 (13)−0.0020 (12)−0.0043 (11)
C70.0514 (15)0.0534 (12)0.0438 (11)0.0041 (11)−0.0018 (10)0.0018 (10)
C80.0599 (17)0.0689 (15)0.0521 (13)−0.0055 (14)0.0088 (13)−0.0060 (12)
C90.0538 (16)0.0566 (13)0.0450 (12)0.0004 (12)0.0022 (11)−0.0006 (10)
C100.0558 (16)0.0580 (13)0.0507 (13)−0.0014 (12)0.0024 (12)−0.0003 (11)
C110.070 (2)0.0852 (19)0.0725 (17)−0.0151 (16)0.0033 (15)−0.0177 (15)
C120.0580 (19)0.090 (2)0.0763 (19)−0.0105 (16)0.0148 (15)−0.0134 (16)
C130.072 (3)0.124 (5)0.108 (6)0.039 (3)−0.021 (4)−0.065 (4)
C140.136 (8)0.165 (9)0.115 (6)0.033 (7)0.001 (5)0.023 (6)
C13'0.072 (3)0.124 (5)0.108 (6)0.039 (3)−0.021 (4)−0.065 (4)
C14'0.136 (8)0.165 (9)0.115 (6)0.033 (7)0.001 (5)0.023 (6)
C150.059 (4)0.031 (4)0.0631 (17)−0.024 (4)0.0240 (16)−0.001 (2)
C160.087 (3)0.067 (3)0.105 (4)0.001 (3)0.026 (4)−0.022 (3)
C170.122 (5)0.085 (5)0.108 (8)0.000 (4)0.058 (7)−0.028 (5)
C180.133 (8)0.098 (8)0.098 (5)−0.045 (8)0.057 (6)−0.038 (5)
C190.100 (7)0.149 (8)0.0579 (19)−0.034 (6)0.029 (3)−0.017 (3)
C200.069 (6)0.102 (2)0.043 (4)−0.020 (3)0.028 (3)0.007 (2)
C15'0.059 (4)0.031 (4)0.0631 (17)−0.024 (4)0.0240 (16)−0.001 (2)
C16'0.087 (3)0.067 (3)0.105 (4)0.001 (3)0.026 (4)−0.022 (3)
C17'0.122 (5)0.085 (5)0.108 (8)0.000 (4)0.058 (7)−0.028 (5)
C18'0.133 (8)0.098 (8)0.098 (5)−0.045 (8)0.057 (6)−0.038 (5)
C19'0.100 (7)0.149 (8)0.0579 (19)−0.034 (6)0.029 (3)−0.017 (3)
C20'0.069 (6)0.102 (2)0.043 (4)−0.020 (3)0.028 (3)0.007 (2)

Geometric parameters (Å, °)

S1—C11.733 (2)C12—H12C0.9701
S1—C71.752 (3)C12—H12D0.9701
O1—C81.238 (3)C13—C141.305 (10)
N1—C71.307 (3)C13—H130.9300
N1—C61.383 (3)C14—H14A0.9300
N2—C101.341 (3)C14—H14B0.9300
N2—N31.393 (3)C13'—C14'1.289 (9)
N2—C121.459 (3)C13'—H13'0.9300
N3—C81.391 (4)C14'—H14C0.9300
N3—C15'1.430 (6)C14'—H14D0.9300
N3—C151.438 (6)C15—C161.3900
C1—C61.392 (4)C15—C201.3900
C1—C21.395 (4)C16—C171.3900
C2—C31.369 (4)C16—H160.9300
C2—H20.9300C17—C181.3900
C3—C41.388 (5)C17—H170.9300
C3—H30.9300C18—C191.3900
C4—C51.363 (4)C18—H180.9300
C4—H40.9300C19—C201.3900
C5—C61.399 (4)C19—H190.9300
C5—H50.9300C20—H200.9300
C7—C91.451 (3)C15'—C16'1.3900
C8—C91.425 (3)C15'—C20'1.3900
C9—C101.368 (4)C16'—C17'1.3900
C10—C111.492 (4)C16'—H16'0.9300
C11—H11A0.9600C17'—C18'1.3900
C11—H11B0.9600C17'—H17'0.9300
C11—H11C0.9600C18'—C19'1.3900
C12—C13'1.525 (9)C18'—H18'0.9300
C12—C131.551 (8)C19'—C20'1.3900
C12—H12A0.9700C19'—H19'0.9300
C12—H12B0.9700C20'—H20'0.9300
C1—S1—C788.53 (12)H12A—C12—H12B108.5
C7—N1—C6110.1 (2)C13'—C12—H12C121.0
C10—N2—N3108.3 (2)C13—C12—H12C110.8
C10—N2—C12126.9 (2)C13'—C12—H12D116.7
N3—N2—C12122.1 (2)H12C—C12—H12D104.1
C8—N3—N2108.7 (2)C14—C13—C12117.5 (15)
C8—N3—C15'128.5 (7)C14—C13—H13121.3
N2—N3—C15'117.3 (6)C12—C13—H13121.3
C8—N3—C15118.9 (7)C13—C14—H14A120.0
N2—N3—C15130.3 (6)C13—C14—H14B120.0
C6—C1—C2121.4 (2)H14A—C14—H14B120.0
C6—C1—S1109.81 (19)C14'—C13'—C12128.4 (15)
C2—C1—S1128.8 (2)C14'—C13'—H13'115.8
C3—C2—C1118.2 (3)C12—C13'—H13'115.8
C3—C2—H2120.9C13'—C14'—H14C120.0
C1—C2—H2120.9C13'—C14'—H14D120.0
C2—C3—C4121.2 (3)H14C—C14'—H14D120.0
C2—C3—H3119.4C16—C15—C20120.0
C4—C3—H3119.4C16—C15—N3127.6 (11)
C5—C4—C3120.6 (3)C20—C15—N3111.0 (10)
C5—C4—H4119.7C15—C16—C17120.0
C3—C4—H4119.7C15—C16—H16120.0
C4—C5—C6119.9 (3)C17—C16—H16120.0
C4—C5—H5120.0C18—C17—C16120.0
C6—C5—H5120.0C18—C17—H17120.0
N1—C6—C1115.6 (2)C16—C17—H17120.0
N1—C6—C5125.7 (3)C17—C18—C19120.0
C1—C6—C5118.7 (3)C17—C18—H18120.0
N1—C7—C9124.4 (2)C19—C18—H18120.0
N1—C7—S1115.99 (19)C20—C19—C18120.0
C9—C7—S1119.57 (17)C20—C19—H19120.0
O1—C8—N3123.1 (2)C18—C19—H19120.0
O1—C8—C9131.8 (3)C19—C20—C15120.0
N3—C8—C9105.0 (2)C19—C20—H20120.0
C10—C9—C8108.3 (2)C15—C20—H20120.0
C10—C9—C7128.8 (2)C16'—C15'—C20'120.0
C8—C9—C7122.9 (2)C16'—C15'—N3111.8 (10)
N2—C10—C9109.4 (2)C20'—C15'—N3125.8 (11)
N2—C10—C11121.2 (3)C15'—C16'—C17'120.0
C9—C10—C11129.4 (2)C15'—C16'—H16'120.0
C10—C11—H11A109.5C17'—C16'—H16'120.0
C10—C11—H11B109.5C18'—C17'—C16'120.0
H11A—C11—H11B109.5C18'—C17'—H17'120.0
C10—C11—H11C109.5C16'—C17'—H17'120.0
H11A—C11—H11C109.5C19'—C18'—C17'120.0
H11B—C11—H11C109.5C19'—C18'—H18'120.0
N2—C12—C13'112.3 (9)C17'—C18'—H18'120.0
N2—C12—C13107.8 (9)C18'—C19'—C20'120.0
N2—C12—H12A110.1C18'—C19'—H19'120.0
C13'—C12—H12A118.2C20'—C19'—H19'120.0
C13—C12—H12A110.1C19'—C20'—C15'120.0
N2—C12—H12B110.1C19'—C20'—H20'120.0
C13—C12—H12B110.1C15'—C20'—H20'120.0
C10—N2—N3—C85.6 (3)C12—N2—C10—C1113.0 (4)
C12—N2—N3—C8168.3 (2)C8—C9—C10—N22.0 (3)
C10—N2—N3—C15'161.9 (8)C7—C9—C10—N2179.5 (2)
C12—N2—N3—C15'−35.5 (8)C8—C9—C10—C11−177.2 (3)
C10—N2—N3—C15168.7 (9)C7—C9—C10—C110.3 (5)
C12—N2—N3—C15−28.7 (9)C10—N2—C12—C13'77.9 (7)
C7—S1—C1—C61.10 (18)N3—N2—C12—C13'−81.3 (7)
C7—S1—C1—C2179.7 (2)C10—N2—C12—C1364.1 (7)
C6—C1—C2—C3−0.8 (4)N3—N2—C12—C13−95.2 (7)
S1—C1—C2—C3−179.3 (2)N2—C12—C13—C14−142.4 (14)
C1—C2—C3—C4−0.1 (4)C13'—C12—C13—C14106 (7)
C2—C3—C4—C50.8 (5)N2—C12—C13'—C14'−108 (2)
C3—C4—C5—C6−0.6 (5)C13—C12—C13'—C14'−35 (6)
C7—N1—C6—C10.3 (3)C8—N3—C15—C16−133.0 (8)
C7—N1—C6—C5179.4 (3)N2—N3—C15—C1665.4 (10)
C2—C1—C6—N1−179.8 (2)C15'—N3—C15—C1691 (6)
S1—C1—C6—N1−1.1 (3)C8—N3—C15—C2060.6 (8)
C2—C1—C6—C51.0 (4)N2—N3—C15—C20−101.0 (10)
S1—C1—C6—C5179.8 (2)C15'—N3—C15—C20−75 (6)
C4—C5—C6—N1−179.4 (3)C20—C15—C16—C170.0
C4—C5—C6—C1−0.3 (4)N3—C15—C16—C17−165.3 (9)
C6—N1—C7—C9−177.2 (2)C15—C16—C17—C180.0
C6—N1—C7—S10.6 (3)C16—C17—C18—C190.0
C1—S1—C7—N1−1.01 (19)C17—C18—C19—C200.0
C1—S1—C7—C9176.89 (19)C18—C19—C20—C150.0
N2—N3—C8—O1176.1 (3)C16—C15—C20—C190.0
C15'—N3—C8—O123.3 (8)N3—C15—C20—C19167.6 (9)
C15—N3—C8—O110.8 (7)C8—N3—C15'—C16'−121.9 (9)
N2—N3—C8—C9−4.3 (3)N2—N3—C15'—C16'87.4 (7)
C15'—N3—C8—C9−157.0 (7)C15—N3—C15'—C16'−71 (6)
C15—N3—C8—C9−169.5 (7)C8—N3—C15'—C20'40.7 (11)
O1—C8—C9—C10−178.9 (3)N2—N3—C15'—C20'−110.1 (9)
N3—C8—C9—C101.4 (3)C15—N3—C15'—C20'92 (6)
O1—C8—C9—C73.4 (5)C20'—C15'—C16'—C17'0.0
N3—C8—C9—C7−176.2 (2)N3—C15'—C16'—C17'163.7 (10)
N1—C7—C9—C107.8 (4)C15'—C16'—C17'—C18'0.0
S1—C7—C9—C10−169.9 (2)C16'—C17'—C18'—C19'0.0
N1—C7—C9—C8−175.0 (2)C17'—C18'—C19'—C20'0.0
S1—C7—C9—C87.2 (3)C18'—C19'—C20'—C15'0.0
N3—N2—C10—C9−4.7 (3)C16'—C15'—C20'—C19'0.0
C12—N2—C10—C9−166.3 (3)N3—C15'—C20'—C19'−161.3 (9)
N3—N2—C10—C11174.6 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.932.593.318 (3)135
C12—H12A···O1ii0.972.513.404 (4)152
C12—H12C···O1ii0.972.483.404 (4)159

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+3/2, y+1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5047).

References

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  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

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