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

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ISSN: 2056-9890

5-Cyclo­hexyl-2-(3-fluoro­phen­yl)-3-methyl­sulfinyl-1-benzo­furan

aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea, and bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
*Correspondence e-mail: uklee@pknu.ac.kr

(Received 20 February 2012; accepted 24 February 2012; online 3 March 2012)

In the title compound, C21H21FO2S, the cyclo­hexyl ring adopts a chair conformation. The 3-fluoro­phenyl ring makes a dihedral angle of 38.38 (6)° with the mean plane [r.m.s. deviation = 0.010 (1) Å] of the benzofuran fragment. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2011a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011a). Acta Cryst. E67, o281.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011b). Acta Cryst. E67, o470.]).

[Scheme 1]

Experimental

Crystal data
  • C21H21FO2S

  • Mr = 356.44

  • Orthorhombic, P n a 21

  • a = 12.7767 (10) Å

  • b = 13.0764 (10) Å

  • c = 10.7711 (8) Å

  • V = 1799.6 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.20 mm−1

  • T = 173 K

  • 0.34 × 0.24 × 0.20 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.935, Tmax = 0.961

  • 17893 measured reflections

  • 4503 independent reflections

  • 4036 reflections with I > 2σ(I)

  • Rint = 0.058

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.096

  • S = 1.03

  • 4503 reflections

  • 227 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.25 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2131 Friedel pairs

  • Flack parameter: −0.07 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C21—H21B⋯O2i 0.98 2.30 3.276 (3) 176
Symmetry code: (i) [-x+1, -y, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SADABS 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

As a part of our ongoing study of 5-cyclohexyl-3-methylsulfinyl-1-benzofuran derivatives containing either 2-phenyl (Choi et al., 2011a) or 2-(4-fluorophenyl) (Choi et al., 2011b) substituents, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.010 (1) Å from the least-squares plane defined by the nine constituent atoms. The cyclohexyl ring is in the chair form. The dihedral angle between the 3-fluorophenyl ring and the mean plane of the benzofurn fragment is 38.38 (6)°. The crystal packing is stabilized by weak intermolecular C–H···O hydrogen bonds (Table 1).

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2011a,b).

Experimental top

77% 3-Chloroperoxybenzoic acid (224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-cyclohexyl-2-(3-fluorophenyl)-3-methylsulfanyl-1-benzofuran (306 mg, 0.9 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 4 h., the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane-ethyl acetate, 1:1 v/v) to afford the title compound as a colorless solid [yield 76%, m.p. 443-444 K; Rf = 0.55 (hexane-ethyl acetate, 1:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in acetone at room temperature.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C–H = 0.95 Å for aryl, 1.0 Å for methine, 0.99 Å for methylene and 0.98 Å for methyl H atoms, respectively. Uiso(H) =1.2Ueq(C) for aryl, methine, and methylene, and 1.5Ueq(C) for methyl H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
5-Cyclohexyl-2-(3-fluorophenyl)-3-methylsulfinyl-1-benzofuran top
Crystal data top
C21H21FO2SDx = 1.316 Mg m3
Mr = 356.44Melting point: 443 K
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 4473 reflections
a = 12.7767 (10) Åθ = 2.5–28.1°
b = 13.0764 (10) ŵ = 0.20 mm1
c = 10.7711 (8) ÅT = 173 K
V = 1799.6 (2) Å3Block, colourless
Z = 40.34 × 0.24 × 0.20 mm
F(000) = 752
Data collection top
Bruker SMART APEXII CCD
diffractometer
4503 independent reflections
Radiation source: rotating anode4036 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.058
Detector resolution: 10.0 pixels mm-1θmax = 28.4°, θmin = 2.2°
ϕ and ω scansh = 1717
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1716
Tmin = 0.935, Tmax = 0.961l = 1414
17893 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.096 w = 1/[σ2(Fo2) + (0.0426P)2 + 0.2167P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
4503 reflectionsΔρmax = 0.33 e Å3
227 parametersΔρmin = 0.25 e Å3
1 restraintAbsolute structure: Flack (1983), 2131 Friedel pairs
0 constraintsAbsolute structure parameter: 0.07 (7)
Primary atom site location: structure-invariant direct methods
Crystal data top
C21H21FO2SV = 1799.6 (2) Å3
Mr = 356.44Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 12.7767 (10) ŵ = 0.20 mm1
b = 13.0764 (10) ÅT = 173 K
c = 10.7711 (8) Å0.34 × 0.24 × 0.20 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
4503 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
4036 reflections with I > 2σ(I)
Tmin = 0.935, Tmax = 0.961Rint = 0.058
17893 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.096Δρmax = 0.33 e Å3
S = 1.03Δρmin = 0.25 e Å3
4503 reflectionsAbsolute structure: Flack (1983), 2131 Friedel pairs
227 parametersAbsolute structure parameter: 0.07 (7)
1 restraint
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.56575 (3)0.02701 (3)0.35040 (5)0.02691 (11)
F10.77633 (15)0.11534 (12)0.03264 (18)0.0792 (6)
O10.46206 (10)0.30803 (10)0.29361 (13)0.0277 (3)
O20.56405 (11)0.00184 (12)0.48474 (14)0.0390 (4)
C10.49571 (12)0.14257 (13)0.33717 (18)0.0234 (3)
C20.40393 (13)0.17197 (14)0.40656 (17)0.0231 (3)
C30.33673 (13)0.12486 (14)0.49109 (16)0.0254 (4)
H30.34750.05550.51430.031*
C40.25446 (14)0.17975 (15)0.54083 (17)0.0257 (4)
C50.24014 (14)0.28249 (15)0.5060 (2)0.0296 (4)
H50.18330.31960.54080.036*
C60.30589 (14)0.33145 (15)0.42275 (19)0.0287 (4)
H60.29570.40090.39970.034*
C70.38672 (13)0.27399 (14)0.37531 (16)0.0260 (4)
C80.52756 (14)0.22666 (14)0.27291 (16)0.0256 (4)
C90.17818 (14)0.12816 (16)0.62864 (17)0.0287 (4)
H90.20640.05850.64690.034*
C100.16664 (19)0.1834 (2)0.7521 (2)0.0443 (5)
H10A0.14390.25470.73670.053*
H10B0.23540.18580.79430.053*
C110.08727 (19)0.1306 (2)0.8365 (2)0.0554 (7)
H11A0.11530.06340.86250.067*
H11B0.07670.17250.91210.067*
C120.01698 (19)0.1153 (2)0.7722 (3)0.0573 (8)
H12A0.06420.07610.82730.069*
H12B0.04950.18270.75640.069*
C130.00474 (18)0.0591 (2)0.6512 (3)0.0494 (6)
H13A0.07360.05400.60950.059*
H13B0.02060.01120.66760.059*
C140.07219 (16)0.1139 (2)0.5661 (2)0.0405 (5)
H14A0.04340.18160.54310.049*
H14B0.08130.07370.48900.049*
C150.61838 (13)0.24653 (16)0.19341 (17)0.0269 (4)
C160.65392 (17)0.17134 (18)0.1135 (2)0.0389 (5)
H160.61720.10860.10510.047*
C170.74380 (18)0.18950 (19)0.0462 (2)0.0457 (6)
C180.79812 (17)0.27964 (19)0.0536 (2)0.0421 (5)
H180.86040.28960.00690.051*
C190.76030 (16)0.35559 (19)0.1303 (2)0.0376 (5)
H190.79570.41940.13490.045*
C200.67083 (14)0.33938 (16)0.20081 (19)0.0306 (4)
H200.64550.39170.25410.037*
C210.47422 (18)0.05631 (16)0.2771 (2)0.0378 (5)
H21A0.50090.12660.27940.057*
H21B0.46440.03520.19050.057*
H21C0.40710.05300.32090.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.02477 (19)0.0252 (2)0.0307 (2)0.00363 (16)0.00124 (19)0.0016 (2)
F10.0930 (12)0.0564 (10)0.0883 (13)0.0007 (9)0.0641 (10)0.0086 (9)
O10.0257 (6)0.0243 (7)0.0332 (7)0.0006 (5)0.0024 (5)0.0051 (6)
O20.0457 (9)0.0377 (8)0.0335 (8)0.0094 (7)0.0076 (7)0.0065 (7)
C10.0219 (7)0.0237 (8)0.0246 (9)0.0008 (6)0.0011 (7)0.0004 (8)
C20.0207 (7)0.0243 (9)0.0243 (8)0.0011 (7)0.0022 (6)0.0010 (7)
C30.0255 (8)0.0236 (9)0.0272 (9)0.0014 (7)0.0001 (7)0.0023 (7)
C40.0246 (9)0.0267 (10)0.0256 (9)0.0020 (7)0.0008 (7)0.0007 (7)
C50.0248 (9)0.0291 (10)0.0350 (10)0.0042 (7)0.0020 (7)0.0021 (8)
C60.0279 (9)0.0232 (9)0.0352 (10)0.0026 (7)0.0013 (8)0.0013 (8)
C70.0219 (8)0.0262 (9)0.0301 (10)0.0030 (7)0.0022 (7)0.0023 (7)
C80.0244 (8)0.0264 (10)0.0260 (9)0.0005 (7)0.0019 (7)0.0011 (7)
C90.0284 (9)0.0306 (10)0.0271 (9)0.0055 (7)0.0042 (7)0.0033 (8)
C100.0440 (12)0.0575 (15)0.0315 (11)0.0056 (11)0.0084 (9)0.0057 (10)
C110.0643 (15)0.0647 (17)0.0373 (13)0.0022 (12)0.0242 (12)0.0026 (13)
C120.0434 (13)0.0520 (15)0.077 (2)0.0069 (12)0.0309 (13)0.0186 (14)
C130.0353 (11)0.0559 (16)0.0571 (15)0.0109 (11)0.0033 (10)0.0208 (12)
C140.0383 (12)0.0457 (14)0.0376 (11)0.0115 (10)0.0014 (9)0.0124 (10)
C150.0250 (8)0.0297 (10)0.0261 (9)0.0002 (7)0.0008 (7)0.0066 (7)
C160.0445 (12)0.0335 (12)0.0387 (12)0.0035 (9)0.0140 (9)0.0040 (9)
C170.0474 (13)0.0440 (14)0.0457 (13)0.0073 (11)0.0228 (11)0.0087 (11)
C180.0297 (10)0.0564 (15)0.0402 (12)0.0000 (10)0.0101 (9)0.0163 (11)
C190.0295 (10)0.0448 (13)0.0386 (11)0.0125 (9)0.0027 (9)0.0095 (10)
C200.0289 (9)0.0315 (11)0.0312 (10)0.0024 (8)0.0044 (8)0.0049 (8)
C210.0447 (12)0.0281 (10)0.0406 (12)0.0025 (9)0.0070 (9)0.0039 (9)
Geometric parameters (Å, º) top
S1—O21.4954 (15)C11—C121.515 (4)
S1—C11.7620 (17)C11—H11A0.9900
S1—C211.783 (2)C11—H11B0.9900
F1—C171.355 (3)C12—C131.505 (4)
O1—C81.372 (2)C12—H12A0.9900
O1—C71.378 (2)C12—H12B0.9900
C1—C81.361 (3)C13—C141.523 (3)
C1—C21.443 (2)C13—H13A0.9900
C2—C71.393 (3)C13—H13B0.9900
C2—C31.395 (2)C14—H14A0.9900
C3—C41.381 (2)C14—H14B0.9900
C3—H30.9500C15—C161.383 (3)
C4—C51.407 (3)C15—C201.389 (3)
C4—C91.516 (3)C16—C171.378 (3)
C5—C61.385 (3)C16—H160.9500
C5—H50.9500C17—C181.370 (3)
C6—C71.376 (3)C18—C191.379 (3)
C6—H60.9500C18—H180.9500
C8—C151.465 (2)C19—C201.389 (3)
C9—C101.520 (3)C19—H190.9500
C9—C141.524 (3)C20—H200.9500
C9—H91.0000C21—H21A0.9800
C10—C111.527 (3)C21—H21B0.9800
C10—H10A0.9900C21—H21C0.9800
C10—H10B0.9900
O2—S1—C1106.69 (9)C10—C11—H11B109.3
O2—S1—C21105.37 (10)H11A—C11—H11B107.9
C1—S1—C2198.93 (9)C13—C12—C11111.69 (19)
C8—O1—C7106.23 (14)C13—C12—H12A109.3
C8—C1—C2106.92 (15)C11—C12—H12A109.3
C8—C1—S1125.59 (13)C13—C12—H12B109.3
C2—C1—S1126.83 (13)C11—C12—H12B109.3
C7—C2—C3118.91 (16)H12A—C12—H12B107.9
C7—C2—C1104.97 (15)C12—C13—C14111.0 (2)
C3—C2—C1136.11 (17)C12—C13—H13A109.4
C4—C3—C2119.48 (17)C14—C13—H13A109.4
C4—C3—H3120.3C12—C13—H13B109.4
C2—C3—H3120.3C14—C13—H13B109.4
C3—C4—C5119.46 (17)H13A—C13—H13B108.0
C3—C4—C9120.00 (17)C13—C14—C9111.42 (18)
C5—C4—C9120.51 (16)C13—C14—H14A109.3
C6—C5—C4122.35 (17)C9—C14—H14A109.3
C6—C5—H5118.8C13—C14—H14B109.3
C4—C5—H5118.8C9—C14—H14B109.3
C7—C6—C5116.31 (17)H14A—C14—H14B108.0
C7—C6—H6121.8C16—C15—C20119.90 (18)
C5—C6—H6121.8C16—C15—C8119.84 (18)
C6—C7—O1125.82 (17)C20—C15—C8120.22 (18)
C6—C7—C2123.48 (17)C17—C16—C15118.6 (2)
O1—C7—C2110.69 (15)C17—C16—H16120.7
C1—C8—O1111.19 (15)C15—C16—H16120.7
C1—C8—C15132.60 (17)F1—C17—C18119.79 (19)
O1—C8—C15116.14 (16)F1—C17—C16117.5 (2)
C4—C9—C10113.34 (18)C18—C17—C16122.7 (2)
C4—C9—C14110.48 (16)C17—C18—C19118.5 (2)
C10—C9—C14111.02 (18)C17—C18—H18120.8
C4—C9—H9107.2C19—C18—H18120.8
C10—C9—H9107.2C18—C19—C20120.4 (2)
C14—C9—H9107.2C18—C19—H19119.8
C9—C10—C11111.7 (2)C20—C19—H19119.8
C9—C10—H10A109.3C19—C20—C15119.9 (2)
C11—C10—H10A109.3C19—C20—H20120.0
C9—C10—H10B109.3C15—C20—H20120.0
C11—C10—H10B109.3S1—C21—H21A109.5
H10A—C10—H10B107.9S1—C21—H21B109.5
C12—C11—C10111.8 (2)H21A—C21—H21B109.5
C12—C11—H11A109.3S1—C21—H21C109.5
C10—C11—H11A109.3H21A—C21—H21C109.5
C12—C11—H11B109.3H21B—C21—H21C109.5
O2—S1—C1—C8133.15 (16)C7—O1—C8—C15176.61 (15)
C21—S1—C1—C8117.75 (17)C3—C4—C9—C10125.5 (2)
O2—S1—C1—C236.29 (18)C5—C4—C9—C1056.7 (2)
C21—S1—C1—C272.81 (18)C3—C4—C9—C14109.2 (2)
C8—C1—C2—C71.11 (19)C5—C4—C9—C1468.6 (2)
S1—C1—C2—C7172.15 (13)C4—C9—C10—C11178.61 (19)
C8—C1—C2—C3177.8 (2)C14—C9—C10—C1153.6 (3)
S1—C1—C2—C36.8 (3)C9—C10—C11—C1253.3 (3)
C7—C2—C3—C40.6 (3)C10—C11—C12—C1354.5 (3)
C1—C2—C3—C4179.4 (2)C11—C12—C13—C1455.9 (3)
C2—C3—C4—C50.4 (3)C12—C13—C14—C956.4 (3)
C2—C3—C4—C9177.44 (16)C4—C9—C14—C13178.2 (2)
C3—C4—C5—C60.0 (3)C10—C9—C14—C1355.2 (3)
C9—C4—C5—C6177.75 (18)C1—C8—C15—C1639.0 (3)
C4—C5—C6—C70.0 (3)O1—C8—C15—C16144.42 (19)
C5—C6—C7—O1178.59 (17)C1—C8—C15—C20139.0 (2)
C5—C6—C7—C20.2 (3)O1—C8—C15—C2037.6 (2)
C8—O1—C7—C6178.97 (17)C20—C15—C16—C172.5 (3)
C8—O1—C7—C20.04 (19)C8—C15—C16—C17175.5 (2)
C3—C2—C7—C60.5 (3)C15—C16—C17—F1179.1 (2)
C1—C2—C7—C6179.67 (17)C15—C16—C17—C181.3 (4)
C3—C2—C7—O1178.43 (15)F1—C17—C18—C19176.9 (2)
C1—C2—C7—O10.7 (2)C16—C17—C18—C190.9 (4)
C2—C1—C8—O11.1 (2)C17—C18—C19—C201.8 (3)
S1—C1—C8—O1172.33 (13)C18—C19—C20—C150.6 (3)
C2—C1—C8—C15175.59 (19)C16—C15—C20—C191.6 (3)
S1—C1—C8—C154.4 (3)C8—C15—C20—C19176.39 (18)
C7—O1—C8—C10.71 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C21—H21B···O2i0.982.303.276 (3)176
Symmetry code: (i) x+1, y, z1/2.

Experimental details

Crystal data
Chemical formulaC21H21FO2S
Mr356.44
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)173
a, b, c (Å)12.7767 (10), 13.0764 (10), 10.7711 (8)
V3)1799.6 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.20
Crystal size (mm)0.34 × 0.24 × 0.20
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.935, 0.961
No. of measured, independent and
observed [I > 2σ(I)] reflections
17893, 4503, 4036
Rint0.058
(sin θ/λ)max1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.096, 1.03
No. of reflections4503
No. of parameters227
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.25
Absolute structureFlack (1983), 2131 Friedel pairs
Absolute structure parameter0.07 (7)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C21—H21B···O2i0.982.303.276 (3)175.5
Symmetry code: (i) x+1, y, z1/2.
 

Acknowledgements

This work was supported by a Dongeui University Foundation grant (2011).

References

First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.
First citationBruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011a). Acta Cryst. E67, o281.  Web of Science CSD CrossRef IUCr Journals
First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011b). Acta Cryst. E67, o470.  Web of Science CSD CrossRef IUCr Journals
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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