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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

5-Bromo-3-(4-fluoro­phenyl­sulfin­yl)-2-phenyl-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 18 October 2012; accepted 24 October 2012; online 31 October 2012)

In the title compound, C20H12BrFO2S, the dihedral angles between the mean plane [r.m.s. deviation = 0.006 (2) Å] of the benzofuran fragment and the pendant 4-fluoro­phenyl and phenyl rings are 84.98 (5) and 40.98 (6)°, respectively. In the crystal, mol­ecules are linked by C—H⋯O and C—H⋯π inter­actions.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2009[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009). Acta Cryst. E65, o2609.]); Seo et al. (2011[Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o2346.]).

[Scheme 1]

Experimental

Crystal data
  • C20H12BrFO2S

  • Mr = 415.27

  • Triclinic, [P \overline 1]

  • a = 9.2288 (2) Å

  • b = 9.4790 (2) Å

  • c = 10.4939 (2) Å

  • α = 67.396 (1)°

  • β = 89.933 (1)°

  • γ = 82.373 (1)°

  • V = 838.74 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 2.60 mm−1

  • T = 173 K

  • 0.39 × 0.33 × 0.22 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 = 0.557, Tmax = 0.746

  • 15136 measured reflections

  • 3888 independent reflections

  • 3417 reflections with I > 2σ(I)

  • Rint = 0.045

Refinement
  • R[F2 > 2σ(F2)] = 0.030

  • wR(F2) = 0.079

  • S = 1.05

  • 3888 reflections

  • 226 parameters

  • H-atom parameters constrained

  • Δρmax = 0.65 e Å−3

  • Δρmin = −0.74 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C9–C14 phenyl ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C10—H10⋯O2i 0.95 2.41 3.341 (3) 167
C19—H19⋯O1ii 0.95 2.50 3.447 (2) 175
C16—H16⋯Cgiii 0.95 2.99 3.832 (2) 148
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) x, y, z-1; (iii) -x, -y+1, -z+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 studies of 5-bromo-1-benzofuran derivatives containing 2-phenyl-3-phenylsulfinyl (Choi et al., 2009) and 2-(4-fluorophenyl)-3-phenylsulfinyl (Seo et al., 2011) 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 0.006 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angles formed by the mean plane of the benzofuran fragment and the pendant 4-fluorophenyl and phenyl rings are 84.98 (5) and 40.98 (6)°, respectively. In the crystal structure (Fig. 2), molecules are connected by weak C—H···O and C—H···π interactions (Table 1, Cg is the centroid of the C9–C14 2-phenyl ring).

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2009); Seo et al. (2011).

Experimental top

3-Chloroperoxybenzoic acid (77%, 202 mg, 0.9 mmol) was added in small portions to a stirred solution of 5-bromo-3-(4-fluorophenylsulfanyl)-2-phenyl-1-benzofuran (319 mg, 0.8 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 5h, 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, 2:1 v/v) to afford the title compound as a colorless solid [yield 63%, m.p. 445-446 K; Rf = 0.75 (hexane-ethyl acetate, 2:1 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 geometrically positioned and refined using a riding model, with C–H = 0.95 Å for the aryl H atoms. Uiso(H) = 1.2Ueq(C) for the aryl 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 the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
[Figure 2] Fig. 2. A view of the C–H···O and C–H···π interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) - x + 1, - y + 1, - z + 2; (ii) x, y,z - 1; (iii) - x, - y + 1, - z + 2; (iv) x, y, z + 1.]
5-Bromo-3-(4-fluorophenylsulfinyl)-2-phenyl-1-benzofuran top
Crystal data top
C20H12BrFO2SZ = 2
Mr = 415.27F(000) = 416
Triclinic, P1Dx = 1.644 Mg m3
Hall symbol: -P 1Melting point = 446–445 K
a = 9.2288 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.4790 (2) ÅCell parameters from 6293 reflections
c = 10.4939 (2) Åθ = 2.2–27.5°
α = 67.396 (1)°µ = 2.60 mm1
β = 89.933 (1)°T = 173 K
γ = 82.373 (1)°Block, colourless
V = 838.74 (3) Å30.39 × 0.33 × 0.22 mm
Data collection top
Bruker SMART APEXII CCD
diffractometer
3888 independent reflections
Radiation source: rotating anode3417 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.045
Detector resolution: 10.0 pixels mm-1θmax = 27.6°, θmin = 2.1°
ϕ and ω scansh = 1212
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 1212
Tmin = 0.557, Tmax = 0.746l = 1313
15136 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)] = 0.030Hydrogen site location: difference Fourier map
wR(F2) = 0.079H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.032P)2 + 0.4488P]
where P = (Fo2 + 2Fc2)/3
3888 reflections(Δ/σ)max = 0.001
226 parametersΔρmax = 0.65 e Å3
0 restraintsΔρmin = 0.74 e Å3
Crystal data top
C20H12BrFO2Sγ = 82.373 (1)°
Mr = 415.27V = 838.74 (3) Å3
Triclinic, P1Z = 2
a = 9.2288 (2) ÅMo Kα radiation
b = 9.4790 (2) ŵ = 2.60 mm1
c = 10.4939 (2) ÅT = 173 K
α = 67.396 (1)°0.39 × 0.33 × 0.22 mm
β = 89.933 (1)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
3888 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3417 reflections with I > 2σ(I)
Tmin = 0.557, Tmax = 0.746Rint = 0.045
15136 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.079H-atom parameters constrained
S = 1.05Δρmax = 0.65 e Å3
3888 reflectionsΔρmin = 0.74 e Å3
226 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*/Ueq
Br10.44656 (2)1.17299 (2)0.60200 (2)0.03743 (9)
S10.34716 (5)0.48730 (6)0.74923 (5)0.02461 (11)
F10.06628 (17)0.76294 (19)0.26600 (15)0.0505 (4)
O10.25847 (16)0.62748 (16)1.05071 (14)0.0266 (3)
O20.49317 (16)0.5237 (2)0.69525 (17)0.0363 (4)
C10.2987 (2)0.5932 (2)0.8526 (2)0.0234 (4)
C20.3270 (2)0.7466 (2)0.8310 (2)0.0241 (4)
C30.3706 (2)0.8705 (2)0.7217 (2)0.0267 (4)
H30.38880.86560.63430.032*
C40.3862 (2)1.0009 (2)0.7466 (2)0.0282 (4)
C50.3610 (2)1.0122 (3)0.8731 (2)0.0321 (5)
H50.37311.10460.88480.039*
C60.3183 (2)0.8897 (3)0.9821 (2)0.0314 (5)
H60.30120.89461.06970.038*
C70.3020 (2)0.7600 (2)0.9568 (2)0.0255 (4)
C80.2584 (2)0.5276 (2)0.9848 (2)0.0240 (4)
C90.2165 (2)0.3774 (2)1.0659 (2)0.0247 (4)
C100.2675 (2)0.2991 (2)1.2042 (2)0.0288 (4)
H100.32740.34521.24610.035*
C110.2304 (3)0.1551 (3)1.2792 (2)0.0367 (5)
H110.26720.10071.37230.044*
C120.1402 (3)0.0891 (3)1.2200 (3)0.0421 (6)
H120.11400.00971.27290.051*
C130.0878 (3)0.1664 (3)1.0836 (3)0.0403 (5)
H130.02560.12091.04320.048*
C140.1259 (2)0.3097 (3)1.0066 (2)0.0330 (5)
H140.09050.36240.91290.040*
C150.2184 (2)0.5861 (2)0.60419 (19)0.0227 (4)
C160.0772 (2)0.6487 (3)0.6157 (2)0.0299 (4)
H160.04680.65020.70170.036*
C170.0195 (2)0.7090 (3)0.5006 (2)0.0351 (5)
H170.11680.75310.50600.042*
C180.0288 (2)0.7034 (3)0.3788 (2)0.0328 (5)
C190.1680 (3)0.6428 (3)0.3644 (2)0.0320 (5)
H190.19770.64200.27790.038*
C200.2640 (2)0.5827 (2)0.4797 (2)0.0267 (4)
H200.36120.53910.47350.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.04254 (14)0.02593 (13)0.04180 (14)0.00937 (9)0.01229 (10)0.00950 (10)
S10.0270 (2)0.0261 (3)0.0238 (2)0.00184 (18)0.00172 (18)0.0136 (2)
F10.0572 (9)0.0564 (10)0.0337 (7)0.0041 (7)0.0179 (7)0.0169 (7)
O10.0355 (8)0.0270 (7)0.0204 (7)0.0083 (6)0.0049 (5)0.0113 (6)
O20.0255 (7)0.0541 (10)0.0394 (9)0.0050 (7)0.0052 (6)0.0293 (8)
C10.0251 (9)0.0254 (10)0.0215 (9)0.0040 (7)0.0017 (7)0.0112 (8)
C20.0239 (9)0.0264 (10)0.0241 (9)0.0031 (7)0.0015 (7)0.0123 (8)
C30.0288 (10)0.0271 (10)0.0246 (10)0.0045 (8)0.0052 (8)0.0104 (8)
C40.0258 (10)0.0253 (10)0.0318 (10)0.0049 (8)0.0037 (8)0.0090 (9)
C50.0362 (11)0.0275 (11)0.0369 (12)0.0054 (9)0.0012 (9)0.0170 (10)
C60.0402 (12)0.0327 (12)0.0274 (10)0.0070 (9)0.0035 (9)0.0176 (9)
C70.0279 (10)0.0267 (10)0.0231 (9)0.0060 (8)0.0034 (7)0.0103 (8)
C80.0243 (9)0.0276 (10)0.0231 (9)0.0043 (7)0.0002 (7)0.0130 (8)
C90.0247 (9)0.0258 (10)0.0250 (9)0.0042 (7)0.0047 (7)0.0112 (8)
C100.0281 (10)0.0293 (11)0.0279 (10)0.0018 (8)0.0026 (8)0.0107 (9)
C110.0433 (12)0.0293 (12)0.0298 (11)0.0002 (9)0.0084 (9)0.0048 (9)
C120.0493 (14)0.0257 (12)0.0510 (15)0.0111 (10)0.0186 (11)0.0126 (11)
C130.0401 (13)0.0371 (13)0.0515 (15)0.0134 (10)0.0071 (11)0.0233 (12)
C140.0324 (11)0.0363 (12)0.0341 (11)0.0072 (9)0.0014 (9)0.0170 (10)
C150.0267 (9)0.0223 (9)0.0208 (9)0.0064 (7)0.0022 (7)0.0093 (8)
C160.0285 (10)0.0374 (12)0.0265 (10)0.0041 (8)0.0047 (8)0.0155 (9)
C170.0296 (11)0.0419 (13)0.0331 (11)0.0004 (9)0.0009 (9)0.0154 (10)
C180.0405 (12)0.0299 (11)0.0263 (10)0.0058 (9)0.0070 (9)0.0087 (9)
C190.0452 (12)0.0314 (11)0.0215 (10)0.0089 (9)0.0060 (9)0.0116 (9)
C200.0298 (10)0.0261 (10)0.0262 (10)0.0059 (8)0.0072 (8)0.0118 (9)
Geometric parameters (Å, º) top
Br1—C41.900 (2)C9—C101.400 (3)
S1—O21.4923 (16)C10—C111.378 (3)
S1—C11.7609 (19)C10—H100.9500
S1—C151.7941 (19)C11—C121.382 (4)
F1—C181.359 (2)C11—H110.9500
O1—C81.371 (2)C12—C131.385 (4)
O1—C71.375 (2)C12—H120.9500
C1—C81.358 (3)C13—C141.380 (3)
C1—C21.443 (3)C13—H130.9500
C2—C71.390 (3)C14—H140.9500
C2—C31.394 (3)C15—C201.383 (3)
C3—C41.382 (3)C15—C161.383 (3)
C3—H30.9500C16—C171.385 (3)
C4—C51.389 (3)C16—H160.9500
C5—C61.382 (3)C17—C181.371 (3)
C5—H50.9500C17—H170.9500
C6—C71.380 (3)C18—C191.369 (3)
C6—H60.9500C19—C201.383 (3)
C8—C91.454 (3)C19—H190.9500
C9—C141.396 (3)C20—H200.9500
O2—S1—C1107.36 (9)C11—C10—H10120.1
O2—S1—C15105.38 (9)C9—C10—H10120.1
C1—S1—C15100.79 (9)C10—C11—C12120.5 (2)
C8—O1—C7106.44 (15)C10—C11—H11119.8
C8—C1—C2107.19 (17)C12—C11—H11119.8
C8—C1—S1123.20 (15)C11—C12—C13120.2 (2)
C2—C1—S1127.98 (15)C11—C12—H12119.9
C7—C2—C3119.21 (18)C13—C12—H12119.9
C7—C2—C1104.74 (18)C14—C13—C12120.0 (2)
C3—C2—C1136.05 (18)C14—C13—H13120.0
C4—C3—C2116.90 (19)C12—C13—H13120.0
C4—C3—H3121.6C13—C14—C9120.2 (2)
C2—C3—H3121.6C13—C14—H14119.9
C3—C4—C5123.2 (2)C9—C14—H14119.9
C3—C4—Br1118.81 (16)C20—C15—C16120.94 (18)
C5—C4—Br1118.02 (16)C20—C15—S1115.41 (15)
C6—C5—C4120.30 (19)C16—C15—S1123.34 (15)
C6—C5—H5119.8C15—C16—C17119.43 (19)
C4—C5—H5119.8C15—C16—H16120.3
C7—C6—C5116.44 (19)C17—C16—H16120.3
C7—C6—H6121.8C18—C17—C16118.3 (2)
C5—C6—H6121.8C18—C17—H17120.9
O1—C7—C6125.29 (18)C16—C17—H17120.9
O1—C7—C2110.73 (17)F1—C18—C19118.31 (19)
C6—C7—C2124.0 (2)F1—C18—C17118.2 (2)
C1—C8—O1110.88 (17)C19—C18—C17123.52 (19)
C1—C8—C9133.00 (18)C18—C19—C20117.88 (19)
O1—C8—C9116.11 (17)C18—C19—H19121.1
C14—C9—C10119.4 (2)C20—C19—H19121.1
C14—C9—C8120.44 (19)C15—C20—C19119.95 (19)
C10—C9—C8120.11 (18)C15—C20—H20120.0
C11—C10—C9119.7 (2)C19—C20—H20120.0
O2—S1—C1—C8127.11 (17)C7—O1—C8—C9179.50 (16)
C15—S1—C1—C8122.87 (17)C1—C8—C9—C1441.0 (3)
O2—S1—C1—C236.4 (2)O1—C8—C9—C14138.82 (19)
C15—S1—C1—C273.58 (19)C1—C8—C9—C10138.7 (2)
C8—C1—C2—C70.7 (2)O1—C8—C9—C1041.5 (3)
S1—C1—C2—C7164.98 (15)C14—C9—C10—C111.4 (3)
C8—C1—C2—C3179.8 (2)C8—C9—C10—C11178.28 (19)
S1—C1—C2—C314.5 (3)C9—C10—C11—C121.7 (3)
C7—C2—C3—C40.1 (3)C10—C11—C12—C130.9 (4)
C1—C2—C3—C4179.5 (2)C11—C12—C13—C140.1 (4)
C2—C3—C4—C50.2 (3)C12—C13—C14—C90.4 (3)
C2—C3—C4—Br1179.60 (14)C10—C9—C14—C130.4 (3)
C3—C4—C5—C60.1 (3)C8—C9—C14—C13179.3 (2)
Br1—C4—C5—C6179.34 (16)O2—S1—C15—C2040.06 (17)
C4—C5—C6—C70.5 (3)C1—S1—C15—C20151.62 (15)
C8—O1—C7—C6179.2 (2)O2—S1—C15—C16146.37 (18)
C8—O1—C7—C21.1 (2)C1—S1—C15—C1634.81 (19)
C5—C6—C7—O1179.01 (19)C20—C15—C16—C170.2 (3)
C5—C6—C7—C20.6 (3)S1—C15—C16—C17173.42 (17)
C3—C2—C7—O1179.31 (17)C15—C16—C17—C180.4 (3)
C1—C2—C7—O11.1 (2)C16—C17—C18—F1179.9 (2)
C3—C2—C7—C60.4 (3)C16—C17—C18—C190.6 (4)
C1—C2—C7—C6179.24 (19)F1—C18—C19—C20179.91 (19)
C2—C1—C8—O10.0 (2)C17—C18—C19—C200.7 (4)
S1—C1—C8—O1166.47 (13)C16—C15—C20—C190.2 (3)
C2—C1—C8—C9179.8 (2)S1—C15—C20—C19173.95 (16)
S1—C1—C8—C913.7 (3)C18—C19—C20—C150.4 (3)
C7—O1—C8—C10.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O2i0.952.413.341 (3)167
C19—H19···O1ii0.952.503.447 (2)175
C16—H16···Cgiii0.952.993.832 (2)148
Symmetry codes: (i) x+1, y+1, z+2; (ii) x, y, z1; (iii) x, y+1, z+2.

Experimental details

Crystal data
Chemical formulaC20H12BrFO2S
Mr415.27
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)9.2288 (2), 9.4790 (2), 10.4939 (2)
α, β, γ (°)67.396 (1), 89.933 (1), 82.373 (1)
V3)838.74 (3)
Z2
Radiation typeMo Kα
µ (mm1)2.60
Crystal size (mm)0.39 × 0.33 × 0.22
Data collection
DiffractometerBruker SMART APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.557, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections
15136, 3888, 3417
Rint0.045
(sin θ/λ)max1)0.652
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.079, 1.05
No. of reflections3888
No. of parameters226
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.65, 0.74

Computer programs: APEX2 (Bruker, 2009), SAINT (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
C10—H10···O2i0.952.413.341 (3)167.1
C19—H19···O1ii0.952.503.447 (2)175.2
C16—H16···Cgiii0.952.993.832 (2)148.1
Symmetry codes: (i) x+1, y+1, z+2; (ii) x, y, z1; (iii) x, y+1, z+2.
 

Acknowledgements

This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan City.

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. (2009). Acta Cryst. E65, o2609.  Web of Science CSD CrossRef IUCr Journals
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals
First citationSeo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o2346.  Web of Science CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds