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ISSN: 2056-9890

Ethyl 2-benzyl-1-propyl-1H-indole-3-carboxyl­ate

aDepartment of Pharmaceuticals, Tianjin Medical College, Tianjin 300222, People's Republic of China
*Correspondence e-mail: austinmm@126.com

(Received 29 April 2009; accepted 2 May 2009; online 14 May 2009)

In the title compound, C21H23NO2, the dihedral angle between the indole ring system and the benzyl ring is 75.92 (9)°. The crystal packing is controlled by C—H⋯O and C—H⋯π inter­actions.

Related literature

For the synthesis of the title compound, see: Du et al. (2006[Du, Y., Liu, R., Linn, G. & Zhao, K. (2006). Org. Lett. 8, 5919-5922.]). For its precursor, see: Jin et al. (2009[Jin, H., Li, P., Liu, B. & Cheng, X. (2009). Acta Cryst. E65, o236.]).

[Scheme 1]

Experimental

Crystal data
  • C21H23NO2

  • Mr = 321.40

  • Orthorhombic, P n a 21

  • a = 16.231 (3) Å

  • b = 19.479 (4) Å

  • c = 5.5226 (11) Å

  • V = 1746.0 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 113 K

  • 0.20 × 0.16 × 0.12 mm

Data collection
  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.985, Tmax = 0.991

  • 13765 measured reflections

  • 2204 independent reflections

  • 2060 reflections with I > 2σ(I)

  • Rint = 0.044

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.102

  • S = 1.07

  • 2204 reflections

  • 220 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.15 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C2—H2⋯O1i 0.95 2.71 3.653 (3) 173
C9—H9B⋯O1i 0.99 2.88 3.680 (3) 138
C11—H11A⋯O1i 0.98 2.69 3.514 (3) 142
C12—H12A⋯O1 0.99 2.39 3.044 (3) 123
C18—H18⋯O1 0.95 2.96 3.620 (3) 128
C21—H21A⋯O2ii 0.98 2.91 3.555 (3) 124
C3—H3⋯Cgiii 0.95 2.82 3.632 (3) 144
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]; (ii) [-x+1, -y+1, z-{\script{1\over 2}}]; (iii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-1]. Cg is the centroid of the C13–C18 ring.

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. 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: CrystalStructure (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]).

Supporting information


Comment top

Indole chemistry continue to capture the attention of synthetic organic chemists due to indole's pharmaceutical properties. Recently we have reported the crystal structure of (Z)-ethyl 2,4-diphenyl-3-(propylamino)-but-2-enoate(Jin et al., 2009). Starting from this precursor, its indole derivative was prepared according to the method of Du and coworkers. To further study the SAR, we determine the crystal structure of this indole derivative.

In the molecular structure,(I)(Fig. 1), the indole ring is coplanar with a dihedral angle of 0.21 (12)° between its pyrrole ring and fused benzene ring. The indole ring forms an angle of 75.92 (9)° with the benzyl ring.

Related literature top

For the synthesis of the title compound, see: Du et al. (2006). For its precursor, see: Jin et al. (2009). Cg is the centroid of the C13–C18 ring.

Experimental top

The title compound was prepared according to the method of the literature (Du et al., 2006). The crystals fit for X-ray diffraction were grown from a mixture of ethyl actate and petroleum ether.

Refinement top

All H atoms were positioned geometrically (C—H = 0.93–0.97 Å)and refined as riding with Uiso(H) = 1.2Ueq(CH and CH2) or 1.5Ueq(CH3). Friedel Pairs were merged before refinement.

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of molecule one of (I) with the atom-numbering scheme and 50% probability displacement ellipsoids.
Ethyl 2-benzyl-1-propyl-1H-indole-3-carboxylate top
Crystal data top
C21H23NO2F(000) = 688
Mr = 321.40Dx = 1.223 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 5126 reflections
a = 16.231 (3) Åθ = 2.4–27.5°
b = 19.479 (4) ŵ = 0.08 mm1
c = 5.5226 (11) ÅT = 113 K
V = 1746.0 (6) Å3Needle, colourless
Z = 40.20 × 0.16 × 0.12 mm
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
2204 independent reflections
Radiation source: rotating anode2060 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.044
Detector resolution: 7.31 pixels mm-1θmax = 27.5°, θmin = 2.4°
ω and ϕ scansh = 2120
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
k = 2525
Tmin = 0.985, Tmax = 0.991l = 47
13765 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.102 w = 1/[σ2(Fo2) + (0.0496P)2 + 0.3147P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
2204 reflectionsΔρmax = 0.18 e Å3
220 parametersΔρmin = 0.15 e Å3
1 restraintExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.044 (4)
Crystal data top
C21H23NO2V = 1746.0 (6) Å3
Mr = 321.40Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 16.231 (3) ŵ = 0.08 mm1
b = 19.479 (4) ÅT = 113 K
c = 5.5226 (11) Å0.20 × 0.16 × 0.12 mm
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
2204 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
2060 reflections with I > 2σ(I)
Tmin = 0.985, Tmax = 0.991Rint = 0.044
13765 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0441 restraint
wR(F2) = 0.102H-atom parameters constrained
S = 1.07Δρmax = 0.18 e Å3
2204 reflectionsΔρmin = 0.15 e Å3
220 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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*/Ueq
O10.38761 (9)0.34048 (8)0.2851 (4)0.0430 (5)
O20.45086 (8)0.40505 (7)0.0042 (3)0.0357 (4)
N10.62712 (10)0.24714 (8)0.3130 (4)0.0294 (4)
C10.66004 (12)0.28279 (10)0.1183 (4)0.0300 (5)
C20.73763 (13)0.27623 (11)0.0133 (5)0.0355 (5)
H20.77680.24400.07180.043*
C30.75495 (13)0.31898 (11)0.1805 (5)0.0392 (6)
H30.80750.31640.25570.047*
C40.69695 (14)0.36590 (11)0.2680 (5)0.0383 (6)
H40.71070.39410.40230.046*
C50.62019 (13)0.37209 (10)0.1635 (5)0.0339 (5)
H50.58130.40420.22450.041*
C60.60052 (12)0.33007 (10)0.0348 (4)0.0288 (4)
C70.52909 (13)0.32030 (9)0.1883 (4)0.0288 (5)
C80.54835 (12)0.26987 (10)0.3565 (5)0.0290 (4)
C90.67057 (12)0.19227 (10)0.4394 (5)0.0326 (5)
H9A0.64720.18730.60410.039*
H9B0.72930.20520.45680.039*
C100.66510 (12)0.12335 (10)0.3092 (5)0.0336 (5)
H10A0.60660.11030.28900.040*
H10B0.69010.12730.14640.040*
C110.70976 (14)0.06838 (11)0.4534 (5)0.0404 (6)
H11A0.76730.08210.47740.061*
H11B0.70790.02480.36470.061*
H11C0.68300.06270.61120.061*
C120.49933 (13)0.24338 (10)0.5656 (4)0.0315 (5)
H12A0.45300.27530.59630.038*
H12B0.53480.24330.71150.038*
C130.46466 (12)0.17145 (10)0.5295 (4)0.0271 (4)
C140.47834 (13)0.12068 (10)0.7011 (4)0.0317 (5)
H140.51210.13020.83760.038*
C150.44300 (14)0.05585 (11)0.6750 (5)0.0360 (5)
H150.45270.02140.79330.043*
C160.39379 (13)0.04180 (11)0.4763 (5)0.0350 (5)
H160.36920.00220.45890.042*
C170.38041 (13)0.09212 (10)0.3027 (5)0.0331 (5)
H170.34700.08250.16560.040*
C180.41579 (12)0.15656 (10)0.3295 (4)0.0296 (4)
H180.40650.19080.21000.036*
C190.44951 (13)0.35436 (10)0.1705 (4)0.0308 (5)
C200.37460 (14)0.44182 (11)0.0340 (6)0.0410 (6)
H20A0.35650.46410.11800.049*
H20B0.33080.40990.08790.049*
C210.39091 (15)0.49475 (12)0.2251 (5)0.0442 (6)
H21A0.43510.52540.17100.066*
H21B0.34070.52150.25390.066*
H21C0.40760.47190.37550.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0300 (8)0.0423 (8)0.0567 (13)0.0019 (6)0.0131 (9)0.0115 (9)
O20.0274 (7)0.0368 (8)0.0430 (10)0.0020 (6)0.0009 (8)0.0075 (8)
N10.0260 (8)0.0311 (8)0.0312 (10)0.0032 (6)0.0012 (8)0.0027 (8)
C10.0266 (10)0.0306 (9)0.0327 (12)0.0088 (8)0.0015 (9)0.0073 (9)
C20.0254 (10)0.0386 (10)0.0426 (14)0.0055 (8)0.0034 (10)0.0085 (10)
C30.0303 (11)0.0443 (11)0.0430 (15)0.0113 (9)0.0102 (11)0.0075 (12)
C40.0378 (12)0.0397 (11)0.0375 (14)0.0123 (9)0.0062 (11)0.0025 (11)
C50.0336 (11)0.0316 (9)0.0365 (12)0.0097 (8)0.0031 (10)0.0032 (10)
C60.0280 (10)0.0285 (9)0.0299 (11)0.0067 (7)0.0022 (9)0.0053 (9)
C70.0274 (10)0.0270 (9)0.0319 (12)0.0055 (7)0.0028 (9)0.0027 (9)
C80.0268 (10)0.0302 (9)0.0299 (11)0.0059 (8)0.0008 (9)0.0049 (9)
C90.0292 (10)0.0361 (10)0.0325 (12)0.0017 (8)0.0030 (10)0.0023 (10)
C100.0289 (10)0.0353 (10)0.0366 (13)0.0010 (8)0.0005 (10)0.0015 (10)
C110.0380 (12)0.0375 (11)0.0457 (14)0.0001 (9)0.0005 (12)0.0050 (11)
C120.0324 (10)0.0342 (10)0.0278 (12)0.0020 (8)0.0032 (9)0.0037 (9)
C130.0231 (9)0.0308 (9)0.0273 (11)0.0012 (7)0.0046 (8)0.0017 (9)
C140.0288 (10)0.0400 (10)0.0262 (11)0.0006 (9)0.0007 (9)0.0025 (10)
C150.0359 (11)0.0382 (11)0.0338 (12)0.0039 (9)0.0005 (10)0.0059 (10)
C160.0388 (11)0.0308 (9)0.0352 (13)0.0024 (8)0.0057 (10)0.0003 (10)
C170.0336 (11)0.0373 (10)0.0283 (12)0.0038 (8)0.0018 (10)0.0016 (10)
C180.0306 (10)0.0313 (9)0.0271 (11)0.0001 (8)0.0008 (9)0.0017 (9)
C190.0292 (10)0.0280 (9)0.0353 (12)0.0052 (8)0.0025 (10)0.0018 (9)
C200.0327 (11)0.0392 (11)0.0512 (16)0.0003 (9)0.0010 (11)0.0093 (12)
C210.0441 (13)0.0411 (11)0.0474 (16)0.0055 (10)0.0029 (12)0.0099 (12)
Geometric parameters (Å, º) top
O1—C191.218 (3)C10—H10B0.9900
O2—C191.349 (3)C11—H11A0.9800
O2—C201.446 (3)C11—H11B0.9800
N1—C81.374 (3)C11—H11C0.9800
N1—C11.387 (3)C12—C131.523 (3)
N1—C91.458 (3)C12—H12A0.9900
C1—C21.392 (3)C12—H12B0.9900
C1—C61.412 (3)C13—C141.387 (3)
C2—C31.385 (4)C13—C181.391 (3)
C2—H20.9500C14—C151.394 (3)
C3—C41.398 (3)C14—H140.9500
C3—H30.9500C15—C161.384 (3)
C4—C51.378 (3)C15—H150.9500
C4—H40.9500C16—C171.388 (3)
C5—C61.404 (3)C16—H160.9500
C5—H50.9500C17—C181.388 (3)
C6—C71.449 (3)C17—H170.9500
C7—C81.388 (3)C18—H180.9500
C7—C191.455 (3)C20—C211.499 (4)
C8—C121.494 (3)C20—H20A0.9900
C9—C101.526 (3)C20—H20B0.9900
C9—H9A0.9900C21—H21A0.9800
C9—H9B0.9900C21—H21B0.9800
C10—C111.518 (3)C21—H21C0.9800
C10—H10A0.9900
C19—O2—C20116.62 (17)C10—C11—H11C109.5
C8—N1—C1109.44 (18)H11A—C11—H11C109.5
C8—N1—C9127.0 (2)H11B—C11—H11C109.5
C1—N1—C9123.49 (17)C8—C12—C13114.42 (18)
N1—C1—C2128.7 (2)C8—C12—H12A108.7
N1—C1—C6108.43 (17)C13—C12—H12A108.7
C2—C1—C6122.9 (2)C8—C12—H12B108.7
C3—C2—C1116.8 (2)C13—C12—H12B108.7
C3—C2—H2121.6H12A—C12—H12B107.6
C1—C2—H2121.6C14—C13—C18119.03 (18)
C2—C3—C4121.6 (2)C14—C13—C12120.5 (2)
C2—C3—H3119.2C18—C13—C12120.43 (19)
C4—C3—H3119.2C13—C14—C15120.6 (2)
C5—C4—C3121.4 (2)C13—C14—H14119.7
C5—C4—H4119.3C15—C14—H14119.7
C3—C4—H4119.3C16—C15—C14119.9 (2)
C4—C5—C6118.8 (2)C16—C15—H15120.1
C4—C5—H5120.6C14—C15—H15120.1
C6—C5—H5120.6C15—C16—C17119.9 (2)
C5—C6—C1118.65 (19)C15—C16—H16120.1
C5—C6—C7135.6 (2)C17—C16—H16120.1
C1—C6—C7105.70 (19)C18—C17—C16120.0 (2)
C8—C7—C6107.73 (18)C18—C17—H17120.0
C8—C7—C19124.58 (19)C16—C17—H17120.0
C6—C7—C19127.7 (2)C17—C18—C13120.6 (2)
N1—C8—C7108.7 (2)C17—C18—H18119.7
N1—C8—C12121.3 (2)C13—C18—H18119.7
C7—C8—C12129.92 (19)O1—C19—O2121.99 (19)
N1—C9—C10113.02 (19)O1—C19—C7126.6 (2)
N1—C9—H9A109.0O2—C19—C7111.41 (18)
C10—C9—H9A109.0O2—C20—C21106.99 (19)
N1—C9—H9B109.0O2—C20—H20A110.3
C10—C9—H9B109.0C21—C20—H20A110.3
H9A—C9—H9B107.8O2—C20—H20B110.3
C11—C10—C9110.2 (2)C21—C20—H20B110.3
C11—C10—H10A109.6H20A—C20—H20B108.6
C9—C10—H10A109.6C20—C21—H21A109.5
C11—C10—H10B109.6C20—C21—H21B109.5
C9—C10—H10B109.6H21A—C21—H21B109.5
H10A—C10—H10B108.1C20—C21—H21C109.5
C10—C11—H11A109.5H21A—C21—H21C109.5
C10—C11—H11B109.5H21B—C21—H21C109.5
H11A—C11—H11B109.5
C8—N1—C1—C2180.0 (2)C6—C7—C8—C12175.6 (2)
C9—N1—C1—C22.4 (3)C19—C7—C8—C126.3 (4)
C8—N1—C1—C60.2 (2)C8—N1—C9—C1096.0 (3)
C9—N1—C1—C6177.74 (19)C1—N1—C9—C1081.1 (2)
N1—C1—C2—C3179.6 (2)N1—C9—C10—C11178.64 (18)
C6—C1—C2—C30.2 (3)N1—C8—C12—C1375.8 (3)
C1—C2—C3—C40.7 (3)C7—C8—C12—C13107.9 (2)
C2—C3—C4—C50.6 (4)C8—C12—C13—C14127.6 (2)
C3—C4—C5—C60.1 (3)C8—C12—C13—C1855.3 (3)
C4—C5—C6—C10.4 (3)C18—C13—C14—C150.6 (3)
C4—C5—C6—C7179.1 (2)C12—C13—C14—C15176.5 (2)
N1—C1—C6—C5179.83 (18)C13—C14—C15—C160.0 (3)
C2—C1—C6—C50.3 (3)C14—C15—C16—C170.6 (3)
N1—C1—C6—C70.8 (2)C15—C16—C17—C180.5 (3)
C2—C1—C6—C7179.4 (2)C16—C17—C18—C130.1 (3)
C5—C6—C7—C8179.9 (2)C14—C13—C18—C170.7 (3)
C1—C6—C7—C81.1 (2)C12—C13—C18—C17176.49 (19)
C5—C6—C7—C191.8 (4)C20—O2—C19—O10.7 (3)
C1—C6—C7—C19177.0 (2)C20—O2—C19—C7178.6 (2)
C1—N1—C8—C70.5 (2)C8—C7—C19—O15.9 (4)
C9—N1—C8—C7176.92 (19)C6—C7—C19—O1171.8 (2)
C1—N1—C8—C12176.43 (18)C8—C7—C19—O2174.8 (2)
C9—N1—C8—C126.1 (3)C6—C7—C19—O27.5 (3)
C6—C7—C8—N11.0 (2)C19—O2—C20—C21179.8 (2)
C19—C7—C8—N1177.15 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.952.713.653 (3)173
C9—H9B···O1i0.992.883.680 (3)138
C11—H11A···O1i0.982.693.514 (3)142
C12—H12A···O10.992.393.044 (3)123
C18—H18···O10.952.963.620 (3)128
C21—H21A···O2ii0.982.913.555 (3)124
C3—H3···Cgiii0.952.823.632 (3)144
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x+1, y+1, z1/2; (iii) x+1/2, y+1/2, z1.

Experimental details

Crystal data
Chemical formulaC21H23NO2
Mr321.40
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)113
a, b, c (Å)16.231 (3), 19.479 (4), 5.5226 (11)
V3)1746.0 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.20 × 0.16 × 0.12
Data collection
DiffractometerRigaku Saturn CCD area-detector
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.985, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
13765, 2204, 2060
Rint0.044
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.102, 1.07
No. of reflections2204
No. of parameters220
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.15

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku/MSC, 2005).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.952.7083.653 (3)173
C9—H9B···O1i0.992.8803.680 (3)138
C11—H11A···O1i0.982.6863.514 (3)142
C12—H12A···O10.992.3863.044 (3)123
C18—H18···O10.952.9613.620 (3)128
C21—H21A···O2ii0.982.9123.555 (3)124
C3—H3···Cgiii0.952.823.632 (3)144
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x+1, y+1, z1/2; (iii) x+1/2, y+1/2, z1.
 

References

First citationDu, Y., Liu, R., Linn, G. & Zhao, K. (2006). Org. Lett. 8, 5919–5922.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationJin, H., Li, P., Liu, B. & Cheng, X. (2009). Acta Cryst. E65, o236.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationRigaku/MSC (2005). CrystalClear and CrystalStructure. 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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