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

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ISSN: 2056-9890

Ethyl (E)-1-(2-styryl-1H-benzimidazol-1-yl)acetate

aOrdered Matter Science Research Center, Southeast UniVersity, Nanjing 210096, People's Republic of China
*Correspondence e-mail: fuxuequn222@163.com

(Received 23 May 2009; accepted 25 May 2009; online 10 June 2009)

In the title compound, C19H18NO2, the dihedral angle between the benzimidazole and phenyl ring planes is 18.18 (17)°. The atoms of the ethyl side chain are disordered over two sets of sites in a 0.50:0.50 ratio. In the crystal, inter­molecular C—H⋯O hydrogen bonds and C—H⋯π contacts help to consolidate the packing.

Related literature

For further synthetic details, see: Hang & Ye (2008[Hang, T. & Ye, Q. (2008). Acta Cryst. E64, o964.]). For background on benzimidazoles, see: Göker et al. (1999[Göker, H., Ayhan-Kõlcõgil, G., Tuncëbilek, M., Kusë, C., Ertan, R., Kendi, E., Özbey, S., Fort, M., Garcia, C. & Farre, A. (1999). J. Heterocycl. Chem. 51, 2561-2573.]); Özbey et al. (1998[Özbey, S., Kendi, E., Göker, H. & Tuncëbilek, M. (1998). J. Chem. Crystallogr. 28, 461-464.]).

[Scheme 1]

Experimental

Crystal data
  • C19H18N2O2

  • Mr = 307.36

  • Orthorhombic, P c a 21

  • a = 12.021 (2) Å

  • b = 14.369 (3) Å

  • c = 9.7517 (18) Å

  • V = 1684.4 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 298 (2) K

  • 0.25 × 0.25 × 0.20 mm

Data collection
  • Rigaku SCXmini diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) Tmin = 0.884, Tmax = 0.984

  • 16640 measured reflections

  • 2046 independent reflections

  • 1545 reflections with I > 2σ(I)

  • Rint = 0.056

Refinement
  • R[F2 > 2σ(F2)] = 0.058

  • wR(F2) = 0.151

  • S = 1.07

  • 2046 reflections

  • 215 parameters

  • 43 restraints

  • H-atom parameters constrained

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C4—H4B⋯O1i 0.97 2.47 3.409 (4) 162
C4—H4ACg2ii 0.97 2.67 3.577 (4) 156
Symmetry codes: (i) [-x+{\script{1\over 2}}, y, z+{\script{1\over 2}}]; (ii) [x+{\script{1\over 2}}, -y, z]; (iii) [-x, -y, z-{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The benzimidazole ring system is of great interest because of its diverse biological activities while the synthesis and crystal structure analyses of several benzimidazoles have already been reported (Göker et al., 1999; Özbey et al., 1998).

In the structure of the title compound (Fig. 1), the benzimidazole system is essentially planar (dihedral angle 1.17 (2)°). The dihedral angle between the benzimidazole and styryl groups is 17.78 (1)°. The molecule is twisted with the N1—C4—C3—O1 torsion angle of 13.61 (4)° between the ethyl acetate and benzimidazole groups.

In the crystal, intermolecular C—H···O hydrogen bonds (Fig.2) link the molecules to chains along the b axis. In addition the C—H···π contacts (Table 1) further stabilize the crystal structure.

Related literature top

For further synthetic details, see: Hang & Ye (2008). For background on benzimidazoles, see: Göker et al. (1999); Özbey et al. (1998). Cg2 is the centroid of the C5–C10 ring.

Experimental top

The synthesis of (E)-2-styryl-1H-benzimidazole was reported previously (Hang & Ye, 2008). Ethyl 2-bromoacetate (1.65 g. 10 mmol) was added to a solution of (E)-2-styryl-1H-benzo[d]imidazole (2.2 g,10 mmol) and NaH (0.6 g, 26 mmol) in THF (30 ml). After the mixture was stirred for 12 h at room temperature, the precipitate was filtered off and the solution was evaporated in vacuum. The crude product was then crystallized from ethanol to yield colourless prisms of (I).

Refinement top

Anomalous dispersion was negligible and Friedel pairs were merged before refimenent. The positional parameters of all the H atoms were calculated geometrically and refined as riding with Uiso(H) = 1.2Ueq(C,N) or 1.5Ueq(methyl C).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level (all H atoms have been omitted for clarity).
[Figure 2] Fig. 2. A view of the packing of the title compound, stacking along the b axis. Dashed lines indicate hydrogen bonds.
Ethyl (E)-1-(2-styryl-1H-benzimidazol-1-yl)acetate top
Crystal data top
C19H18N2O2F(000) = 652
Mr = 307.36Dx = 1.212 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 3237 reflections
a = 12.021 (2) Åθ = 2.5–27.5°
b = 14.369 (3) ŵ = 0.08 mm1
c = 9.7517 (18) ÅT = 298 K
V = 1684.4 (5) Å3Prism, colourless
Z = 40.25 × 0.25 × 0.20 mm
Data collection top
Rigaku SCXmini
diffractometer
2046 independent reflections
Radiation source: fine-focus sealed tube1545 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 2.8°
CCD_Profile_fitting scansh = 1515
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
k = 1818
Tmin = 0.884, Tmax = 0.984l = 1212
16640 measured reflections
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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0802P)2 + 0.1398P]
where P = (Fo2 + 2Fc2)/3
2046 reflections
215 parametersΔρmax = 0.16 e Å3
43 restraintsΔρmin = 0.25 e Å3
Crystal data top
C19H18N2O2V = 1684.4 (5) Å3
Mr = 307.36Z = 4
Orthorhombic, Pca21Mo Kα radiation
a = 12.021 (2) ŵ = 0.08 mm1
b = 14.369 (3) ÅT = 298 K
c = 9.7517 (18) Å0.25 × 0.25 × 0.20 mm
Data collection top
Rigaku SCXmini
diffractometer
2046 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2005)
1545 reflections with I > 2σ(I)
Tmin = 0.884, Tmax = 0.984Rint = 0.056
16640 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05843 restraints
wR(F2) = 0.151H-atom parameters constrained
S = 1.07Δρmax = 0.16 e Å3
2046 reflectionsΔρmin = 0.25 e Å3
215 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.1633 (2)0.13879 (18)0.1323 (3)0.0509 (6)
N20.0004 (2)0.14329 (18)0.0204 (3)0.0558 (7)
C50.1630 (2)0.0626 (2)0.0454 (3)0.0500 (7)
O10.3290 (2)0.2529 (2)0.0215 (3)0.0743 (7)
O20.4352 (2)0.2271 (2)0.2042 (3)0.0925 (10)
C30.3424 (3)0.2197 (2)0.1332 (4)0.0570 (8)
C60.0611 (3)0.0668 (2)0.0229 (4)0.0543 (8)
C110.0644 (2)0.1847 (2)0.1111 (3)0.0493 (7)
C120.0354 (3)0.2693 (2)0.1853 (4)0.0559 (8)
H12A0.07990.28730.25860.067*
C130.0510 (3)0.3216 (2)0.1534 (4)0.0587 (8)
H13A0.09240.30240.07800.070*
C140.0894 (3)0.4059 (2)0.2221 (4)0.0586 (8)
C40.2583 (3)0.1664 (2)0.2144 (3)0.0539 (7)
H4A0.29320.11130.25240.065*
H4B0.23290.20460.29030.065*
C70.0364 (3)0.0019 (3)0.1204 (4)0.0675 (10)
H7A0.03090.00150.16750.081*
C150.1778 (4)0.4562 (3)0.1668 (5)0.0794 (12)
H15A0.21050.43600.08560.095*
C190.0430 (3)0.4385 (3)0.3420 (4)0.0715 (10)
H19A0.01710.40720.38060.086*
C90.2151 (4)0.0720 (3)0.0755 (4)0.0763 (11)
H9A0.26580.11900.09530.092*
C180.0843 (4)0.5169 (3)0.4058 (5)0.0863 (13)
H18A0.05190.53780.48670.104*
C80.1142 (4)0.0697 (3)0.1441 (5)0.0804 (12)
H8A0.09870.11570.20850.096*
C100.2420 (3)0.0058 (2)0.0215 (4)0.0652 (9)
H10A0.30940.00700.06840.078*
C160.2178 (4)0.5352 (3)0.2300 (6)0.0944 (14)
H16A0.27570.56860.19020.113*
C170.1726 (5)0.5644 (3)0.3512 (6)0.0941 (15)
H17A0.20150.61610.39620.113*
C10.5262 (14)0.283 (2)0.143 (3)0.128 (3)0.50
H1A0.52130.28200.04370.153*0.50
H1B0.52180.34700.17380.153*0.50
C20.628 (3)0.241 (2)0.188 (3)0.137 (8)0.50
H2B0.68990.27320.14680.206*0.50
H2C0.62960.17690.16060.206*0.50
H2D0.63360.24530.28580.206*0.50
C1'0.5333 (14)0.271 (2)0.137 (3)0.128 (3)0.50
H1'A0.55640.23380.05900.153*0.50
H1'B0.51470.33270.10580.153*0.50
C2'0.621 (3)0.275 (2)0.237 (3)0.137 (8)0.50
H2'A0.68390.30700.19820.206*0.50
H2'B0.64290.21300.26220.206*0.50
H2'C0.59580.30780.31670.206*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0473 (13)0.0574 (15)0.0480 (13)0.0008 (12)0.0054 (12)0.0040 (13)
N20.0486 (13)0.0628 (16)0.0560 (15)0.0030 (13)0.0017 (13)0.0031 (15)
C50.0513 (17)0.0551 (17)0.0434 (17)0.0044 (15)0.0014 (14)0.0030 (14)
O10.0745 (16)0.0925 (18)0.0560 (14)0.0139 (14)0.0052 (14)0.0121 (15)
O20.0618 (15)0.125 (2)0.090 (2)0.0270 (16)0.0254 (16)0.043 (2)
C30.0547 (18)0.0639 (19)0.0525 (19)0.0027 (16)0.0054 (15)0.0003 (17)
C60.0513 (18)0.0607 (18)0.0510 (17)0.0093 (15)0.0032 (14)0.0006 (16)
C110.0451 (16)0.0533 (16)0.0495 (17)0.0047 (14)0.0063 (14)0.0020 (15)
C120.0571 (19)0.0557 (18)0.0550 (19)0.0045 (16)0.0044 (15)0.0012 (16)
C130.0571 (19)0.0631 (19)0.0560 (19)0.0008 (16)0.0026 (15)0.0011 (17)
C140.0614 (19)0.0538 (17)0.0604 (19)0.0014 (16)0.0056 (18)0.0043 (17)
C40.0559 (18)0.0615 (16)0.0442 (15)0.0003 (17)0.0074 (15)0.0007 (16)
C70.060 (2)0.074 (2)0.068 (2)0.0138 (19)0.0028 (18)0.015 (2)
C150.082 (3)0.071 (2)0.085 (3)0.016 (2)0.010 (2)0.005 (2)
C190.075 (2)0.073 (2)0.067 (2)0.0104 (19)0.0006 (19)0.005 (2)
C90.082 (3)0.068 (2)0.079 (2)0.010 (2)0.002 (2)0.017 (2)
C180.105 (3)0.080 (3)0.074 (3)0.006 (3)0.003 (3)0.016 (2)
C80.089 (3)0.072 (2)0.080 (3)0.010 (2)0.000 (2)0.027 (2)
C100.0597 (18)0.0716 (19)0.064 (2)0.0050 (18)0.0025 (18)0.0081 (19)
C160.100 (4)0.082 (3)0.101 (3)0.034 (3)0.008 (3)0.003 (3)
C170.112 (4)0.074 (3)0.096 (3)0.025 (3)0.022 (3)0.004 (3)
C10.078 (3)0.160 (7)0.145 (6)0.048 (4)0.024 (4)0.068 (6)
C20.086 (5)0.18 (2)0.151 (19)0.025 (9)0.005 (10)0.031 (12)
C1'0.078 (3)0.160 (7)0.145 (6)0.048 (4)0.024 (4)0.068 (6)
C2'0.086 (5)0.18 (2)0.151 (19)0.025 (9)0.005 (10)0.031 (12)
Geometric parameters (Å, º) top
N1—C111.376 (4)C15—H15A0.9300
N1—C51.384 (4)C19—C181.380 (6)
N1—C41.450 (4)C19—H19A0.9300
N2—C111.314 (4)C9—C101.380 (5)
N2—C61.385 (4)C9—C81.387 (6)
C5—C101.387 (5)C9—H9A0.9300
C5—C61.395 (4)C18—C171.369 (7)
O1—C31.200 (5)C18—H18A0.9300
O2—C31.318 (4)C8—H8A0.9300
O2—C11.482 (9)C10—H10A0.9300
O2—C1'1.485 (9)C16—C171.367 (8)
C3—C41.495 (5)C16—H16A0.9300
C6—C71.402 (5)C17—H17A0.9300
C11—C121.457 (5)C1—C21.434 (10)
C12—C131.318 (5)C1—H1A0.9700
C12—H12A0.9300C1—H1B0.9700
C13—C141.459 (5)C2—H2B0.9600
C13—H13A0.9300C2—H2C0.9600
C14—C191.378 (5)C2—H2D0.9600
C14—C151.393 (5)C1'—C2'1.436 (10)
C4—H4A0.9700C1'—H1'A0.9700
C4—H4B0.9700C1'—H1'B0.9700
C7—C81.370 (6)C2'—H2'A0.9600
C7—H7A0.9300C2'—H2'B0.9600
C15—C161.378 (6)C2'—H2'C0.9600
C11—N1—C5106.6 (2)C10—C9—C8121.3 (4)
C11—N1—C4129.2 (3)C10—C9—H9A119.3
C5—N1—C4123.8 (3)C8—C9—H9A119.3
C11—N2—C6104.9 (3)C17—C18—C19120.7 (5)
N1—C5—C10131.4 (3)C17—C18—H18A119.6
N1—C5—C6105.1 (3)C19—C18—H18A119.6
C10—C5—C6123.5 (3)C7—C8—C9122.2 (4)
C3—O2—C1117.2 (11)C7—C8—H8A118.9
C3—O2—C1'118.4 (10)C9—C8—H8A118.9
C1—O2—C1'8 (3)C9—C10—C5116.3 (4)
O1—C3—O2124.0 (3)C9—C10—H10A121.8
O1—C3—C4126.4 (3)C5—C10—H10A121.8
O2—C3—C4109.6 (3)C17—C16—C15120.0 (5)
N2—C6—C5110.6 (3)C17—C16—H16A120.0
N2—C6—C7130.8 (3)C15—C16—H16A120.0
C5—C6—C7118.7 (3)C16—C17—C18119.4 (4)
N2—C11—N1112.9 (3)C16—C17—H17A120.3
N2—C11—C12124.9 (3)C18—C17—H17A120.3
N1—C11—C12122.2 (3)C2—C1—O2106 (2)
C13—C12—C11123.1 (3)C2—C1—H1A110.5
C13—C12—H12A118.4O2—C1—H1A110.5
C11—C12—H12A118.4C2—C1—H1B110.5
C12—C13—C14127.9 (3)O2—C1—H1B110.5
C12—C13—H13A116.1H1A—C1—H1B108.6
C14—C13—H13A116.1C1—C2—H2B109.5
C19—C14—C15117.4 (4)C1—C2—H2C109.5
C19—C14—C13122.9 (3)H2B—C2—H2C109.5
C15—C14—C13119.6 (3)C1—C2—H2D109.5
N1—C4—C3112.3 (3)H2B—C2—H2D109.5
N1—C4—H4A109.1H2C—C2—H2D109.5
C3—C4—H4A109.1C2'—C1'—O2108 (2)
N1—C4—H4B109.1C2'—C1'—H1'A110.1
C3—C4—H4B109.1O2—C1'—H1'A110.1
H4A—C4—H4B107.9C2'—C1'—H1'B110.1
C8—C7—C6118.0 (4)O2—C1'—H1'B110.1
C8—C7—H7A121.0H1'A—C1'—H1'B108.4
C6—C7—H7A121.0C1'—C2'—H2'A109.5
C16—C15—C14121.4 (5)C1'—C2'—H2'B109.5
C16—C15—H15A119.3H2'A—C2'—H2'B109.5
C14—C15—H15A119.3C1'—C2'—H2'C109.5
C14—C19—C18121.0 (4)H2'A—C2'—H2'C109.5
C14—C19—H19A119.5H2'B—C2'—H2'C109.5
C18—C19—H19A119.5
C11—N1—C5—C10178.2 (4)C12—C13—C14—C15174.9 (4)
C4—N1—C5—C104.8 (5)C11—N1—C4—C391.5 (4)
C11—N1—C5—C60.8 (3)C5—N1—C4—C380.3 (4)
C4—N1—C5—C6174.2 (3)O1—C3—C4—N113.5 (5)
C1—O2—C3—O12.3 (17)O2—C3—C4—N1167.8 (3)
C1'—O2—C3—O16.5 (17)N2—C6—C7—C8178.9 (4)
C1—O2—C3—C4176.4 (16)C5—C6—C7—C80.3 (5)
C1'—O2—C3—C4174.8 (16)C19—C14—C15—C160.4 (6)
C11—N2—C6—C50.7 (4)C13—C14—C15—C16178.8 (4)
C11—N2—C6—C7178.6 (4)C15—C14—C19—C181.2 (6)
N1—C5—C6—N20.1 (3)C13—C14—C19—C18177.9 (4)
C10—C5—C6—N2179.0 (3)C14—C19—C18—C170.0 (7)
N1—C5—C6—C7179.5 (3)C6—C7—C8—C90.1 (7)
C10—C5—C6—C70.4 (5)C10—C9—C8—C70.4 (7)
C6—N2—C11—N11.2 (4)C8—C9—C10—C50.3 (6)
C6—N2—C11—C12180.0 (3)N1—C5—C10—C9178.9 (3)
C5—N1—C11—N21.3 (4)C6—C5—C10—C90.1 (5)
C4—N1—C11—N2174.2 (3)C14—C15—C16—C171.7 (8)
C5—N1—C11—C12179.8 (3)C15—C16—C17—C182.9 (8)
C4—N1—C11—C127.0 (5)C19—C18—C17—C162.0 (8)
N2—C11—C12—C1311.1 (5)C3—O2—C1—C2147.8 (16)
N1—C11—C12—C13170.2 (3)C1'—O2—C1—C247 (14)
C11—C12—C13—C14178.3 (3)C3—O2—C1'—C2'177.1 (14)
C12—C13—C14—C195.9 (6)C1—O2—C1'—C2'94 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···O1i0.972.473.409 (4)162
C4—H4A···Cg2ii0.972.673.577 (4)156
Symmetry codes: (i) x+1/2, y, z+1/2; (ii) x+1/2, y, z.

Experimental details

Crystal data
Chemical formulaC19H18N2O2
Mr307.36
Crystal system, space groupOrthorhombic, Pca21
Temperature (K)298
a, b, c (Å)12.021 (2), 14.369 (3), 9.7517 (18)
V3)1684.4 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.25 × 0.25 × 0.20
Data collection
DiffractometerRigaku SCXmini
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2005)
Tmin, Tmax0.884, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections
16640, 2046, 1545
Rint0.056
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.151, 1.07
No. of reflections2046
No. of parameters215
No. of restraints43
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.16, 0.25

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···O1i0.972.473.409 (4)161.5
C4—H4A···Cg2ii0.972.67023.577 (4)155.90
Symmetry codes: (i) x+1/2, y, z+1/2; (ii) x+1/2, y, z.
 

Acknowledgements

The authors are grateful to the starter fund of Southeast University for financial support to purchase the X-ray diffractometer.

References

First citationGöker, H., Ayhan-Kõlcõgil, G., Tuncëbilek, M., Kusë, C., Ertan, R., Kendi, E., Özbey, S., Fort, M., Garcia, C. & Farre, A. (1999). J. Heterocycl. Chem. 51, 2561–2573.  Google Scholar
First citationHang, T. & Ye, Q. (2008). Acta Cryst. E64, o964.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationÖzbey, S., Kendi, E., Göker, H. & Tuncëbilek, M. (1998). J. Chem. Crystallogr. 28, 461–464.  Google Scholar
First citationRigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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