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

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ISSN: 2056-9890

2-Bromo-1,3-di­phenyl­propan-1,3-dione

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 11 November 2008; accepted 19 November 2008; online 26 November 2008)

The title compound, C15H11BrO2, exists as a diketone in which the two benzoyl groups are nearly perpendicular to each other [dihedral angles = 79.9 (1) and 87.4 (1)° in the two independent mol­ecules].

Related literature

The compound is claimed to exist in the enol form as it condenses with 2-amino­thia­zole and 2-mercaptoimidazoline; see: Robert & Panouse (1979[Robert, J. F. & Panouse, J. J. (1979). J. Heterocycl. Chem. 16, 1201-1207.]). The parent dibenzoyl­methane mol­ecule exists in two modications, as 1,3-diphenyl-1-hydroxy­propen-1-one; see: Kaitner & Meštrović (1993[Kaitner, B. & Meštrović, E. (1993). Acta Cryst. C49, 1523-1525.]); Ozturk et al. (1997[Ozturk, S., Akkurt, M. & Ide, S. (1997). Z. Kristallogr. 212, 808-810.]).

[Scheme 1]

Experimental

Crystal data
  • C15H11BrO2

  • Mr = 303.15

  • Orthorhombic, P c a 21

  • a = 28.0680 (6) Å

  • b = 5.6508 (1) Å

  • c = 15.3741 (3) Å

  • V = 2438.43 (8) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 3.36 mm−1

  • T = 100 (2) K

  • 0.27 × 0.20 × 0.06 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.464, Tmax = 0.824

  • 21610 measured reflections

  • 5562 independent reflections

  • 4774 reflections with I > 2σ(I)

  • Rint = 0.060

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.086

  • S = 0.99

  • 5562 reflections

  • 325 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.76 e Å−3

  • Δρmin = −0.52 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 2644 Fridel pairs

  • Flack parameter: −0.002 (9)

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2008[Westrip, S. P. (2008). publCIF. In preparation.]).

Supporting information


Related literature top

The compound is claimed to exist in the enol form as it condenses with 2-aminothiazole and 2-mercaptoimidazoline; see: Robert & Panouse (1979). The parent dibenzoylmethane molecule exists in two modications, as 1,3-diphenyl-1-hydroxypropen-1-one; see: Kaitner & Meštrović (1993); Ozturk et al. (1997).

Experimental top

The commerically available compound was recrystallized from toluene.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 Å) and were included in the refinement using a riding model approximation, with U(H) set to 1.2U(C).

The (200) reflection was omitted.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid (Barbour, 2001) plot of the two independent molecules of C15H11BrO2 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
2-Bromo-1,3-diphenylpropan-1,3-dione top
Crystal data top
C15H11BrO2F(000) = 1216
Mr = 303.15Dx = 1.652 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 4583 reflections
a = 28.0680 (6) Åθ = 2.6–25.4°
b = 5.6508 (1) ŵ = 3.36 mm1
c = 15.3741 (3) ÅT = 100 K
V = 2438.43 (8) Å3Plate, colorless
Z = 80.27 × 0.20 × 0.06 mm
Data collection top
Bruker SMART APEX
diffractometer
5562 independent reflections
Radiation source: fine-focus sealed tube4774 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.060
ω scansθmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 3635
Tmin = 0.464, Tmax = 0.824k = 77
21610 measured reflectionsl = 1919
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)] = 0.037H-atom parameters constrained
wR(F2) = 0.087 w = 1/[σ2(Fo2) + (0.0511P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max = 0.001
5562 reflectionsΔρmax = 0.76 e Å3
325 parametersΔρmin = 0.52 e Å3
1 restraintAbsolute structure: Flack (1983), 2644 Fridel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.002 (9)
Crystal data top
C15H11BrO2V = 2438.43 (8) Å3
Mr = 303.15Z = 8
Orthorhombic, Pca21Mo Kα radiation
a = 28.0680 (6) ŵ = 3.36 mm1
b = 5.6508 (1) ÅT = 100 K
c = 15.3741 (3) Å0.27 × 0.20 × 0.06 mm
Data collection top
Bruker SMART APEX
diffractometer
5562 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4774 reflections with I > 2σ(I)
Tmin = 0.464, Tmax = 0.824Rint = 0.060
21610 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.087Δρmax = 0.76 e Å3
S = 0.99Δρmin = 0.52 e Å3
5562 reflectionsAbsolute structure: Flack (1983), 2644 Fridel pairs
325 parametersAbsolute structure parameter: 0.002 (9)
1 restraint
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.264659 (13)0.21340 (7)0.50000 (3)0.01660 (9)
Br20.355868 (14)1.36089 (7)0.23689 (3)0.01981 (10)
O10.18018 (11)0.0909 (5)0.52553 (18)0.0212 (7)
O20.17207 (11)0.1525 (5)0.33248 (18)0.0181 (6)
O30.44667 (12)1.6039 (6)0.1914 (2)0.0312 (8)
O40.44450 (11)1.4517 (5)0.39763 (19)0.0216 (7)
C10.11351 (15)0.1585 (6)0.5074 (3)0.0147 (8)
C20.09476 (15)0.3667 (8)0.4735 (3)0.0183 (9)
H20.11530.48460.45050.022*
C30.04576 (15)0.4012 (8)0.4733 (3)0.0188 (9)
H30.03300.54110.44820.023*
C40.01566 (16)0.2367 (7)0.5086 (3)0.0233 (10)
H40.01780.26230.50800.028*
C50.03430 (16)0.0314 (8)0.5455 (3)0.0208 (9)
H50.01360.08180.57110.025*
C60.08317 (16)0.0077 (8)0.5446 (3)0.0194 (9)
H60.09590.14810.56950.023*
C70.16522 (15)0.1006 (7)0.5035 (3)0.0171 (8)
C80.19934 (14)0.2929 (7)0.4686 (3)0.0145 (8)
H80.19060.45050.49360.017*
C90.19594 (15)0.3008 (7)0.3688 (3)0.0150 (8)
C100.22242 (14)0.4836 (7)0.3189 (2)0.0138 (8)
C110.22560 (13)0.4551 (7)0.2283 (3)0.0165 (8)
H110.21210.31960.20130.020*
C120.24831 (16)0.6234 (8)0.1785 (3)0.0168 (9)
H120.25010.60420.11720.020*
C130.26858 (15)0.8212 (8)0.2174 (3)0.0188 (9)
H130.28410.93730.18290.023*
C140.26596 (15)0.8482 (7)0.3067 (3)0.0176 (9)
H140.28000.98300.33340.021*
C150.24308 (15)0.6804 (7)0.3579 (3)0.0153 (8)
H150.24160.70000.41920.018*
C160.39938 (16)1.1076 (8)0.4260 (3)0.0168 (9)
C170.37847 (15)0.9021 (8)0.3946 (3)0.0174 (9)
H170.37850.86900.33410.021*
C180.35758 (18)0.7456 (8)0.4527 (3)0.0198 (10)
H180.34400.60260.43180.024*
C190.3564 (2)0.7951 (9)0.5399 (3)0.0252 (11)
H190.34130.68780.57860.030*
C200.37725 (19)1.0017 (9)0.5725 (3)0.0272 (11)
H200.37691.03410.63310.033*
C210.39847 (16)1.1585 (7)0.5150 (3)0.0214 (10)
H210.41241.30060.53610.026*
C220.42297 (14)1.2851 (8)0.3686 (3)0.0159 (8)
C230.42002 (14)1.2619 (8)0.2686 (3)0.0159 (9)
H230.42561.09420.25050.019*
C240.45729 (14)1.4232 (7)0.2285 (3)0.0187 (8)
C250.50847 (14)1.3574 (7)0.2417 (3)0.0163 (8)
C260.52174 (17)1.1460 (7)0.2826 (3)0.0175 (9)
H260.49801.03400.29850.021*
C270.56937 (15)1.0990 (7)0.3001 (3)0.0170 (9)
H270.57830.95530.32760.020*
C280.60386 (16)1.2646 (8)0.2768 (3)0.0193 (9)
H280.63641.23660.29010.023*
C290.59053 (14)1.4708 (7)0.2339 (3)0.0190 (8)
H290.61411.58090.21590.023*
C300.54305 (15)1.5154 (8)0.2177 (2)0.0179 (9)
H300.53421.65810.18930.022*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.01624 (19)0.01938 (19)0.01417 (16)0.00186 (15)0.00319 (19)0.00273 (19)
Br20.01400 (19)0.0249 (2)0.02058 (18)0.00115 (17)0.0026 (2)0.00051 (18)
O10.0241 (17)0.0178 (16)0.0216 (15)0.0040 (13)0.0017 (12)0.0053 (11)
O20.0206 (17)0.0167 (16)0.0169 (14)0.0018 (12)0.0004 (12)0.0016 (12)
O30.0200 (18)0.026 (2)0.047 (2)0.0031 (14)0.0006 (16)0.0203 (16)
O40.0191 (17)0.0190 (16)0.0269 (16)0.0045 (13)0.0007 (13)0.0065 (13)
C10.018 (2)0.015 (2)0.0107 (18)0.0009 (14)0.0032 (17)0.0021 (18)
C20.023 (2)0.016 (2)0.0162 (19)0.0028 (17)0.0000 (17)0.0040 (15)
C30.020 (2)0.016 (2)0.021 (2)0.0056 (16)0.0044 (17)0.0010 (16)
C40.017 (2)0.027 (3)0.025 (2)0.0053 (16)0.001 (2)0.002 (2)
C50.020 (2)0.027 (3)0.015 (2)0.0058 (19)0.0001 (17)0.0050 (18)
C60.023 (2)0.017 (2)0.018 (2)0.0011 (17)0.0024 (18)0.0005 (17)
C70.024 (2)0.018 (2)0.0094 (16)0.0007 (16)0.0012 (18)0.0010 (19)
C80.015 (2)0.015 (2)0.0140 (16)0.0032 (16)0.0006 (15)0.0054 (16)
C90.016 (2)0.013 (2)0.0155 (18)0.0025 (17)0.0016 (16)0.0046 (15)
C100.011 (2)0.014 (2)0.0168 (19)0.0004 (15)0.0006 (15)0.0013 (16)
C110.0124 (18)0.018 (2)0.019 (2)0.0006 (15)0.0032 (19)0.0013 (18)
C120.022 (2)0.021 (2)0.0079 (17)0.0013 (17)0.0003 (16)0.0039 (17)
C130.020 (2)0.016 (2)0.021 (2)0.0026 (16)0.0036 (17)0.0006 (16)
C140.018 (2)0.015 (2)0.021 (2)0.0008 (17)0.0016 (17)0.0037 (16)
C150.016 (2)0.016 (2)0.0138 (18)0.0020 (16)0.0038 (16)0.0024 (16)
C160.018 (2)0.017 (2)0.0153 (19)0.0037 (17)0.0010 (17)0.0029 (17)
C170.016 (2)0.021 (2)0.0158 (19)0.0024 (17)0.0009 (17)0.0000 (17)
C180.014 (2)0.017 (2)0.028 (3)0.0018 (18)0.000 (2)0.0058 (18)
C190.024 (3)0.026 (3)0.026 (2)0.006 (2)0.007 (2)0.006 (2)
C200.038 (3)0.029 (3)0.014 (2)0.002 (2)0.0012 (19)0.0036 (18)
C210.026 (2)0.017 (2)0.021 (2)0.0014 (17)0.0040 (18)0.0013 (17)
C220.010 (2)0.019 (2)0.0186 (19)0.0059 (17)0.0013 (16)0.0006 (17)
C230.008 (2)0.021 (2)0.0192 (19)0.0036 (16)0.0002 (16)0.0040 (16)
C240.020 (2)0.020 (2)0.016 (2)0.0006 (16)0.000 (2)0.0043 (18)
C250.018 (2)0.0157 (19)0.0155 (18)0.0032 (17)0.004 (2)0.0018 (17)
C260.024 (2)0.012 (2)0.017 (2)0.0009 (17)0.0009 (18)0.0021 (16)
C270.022 (2)0.013 (2)0.0164 (19)0.0042 (16)0.0014 (17)0.0012 (15)
C280.016 (2)0.023 (2)0.019 (2)0.0013 (17)0.0012 (17)0.0073 (18)
C290.021 (2)0.018 (2)0.0180 (17)0.0010 (16)0.003 (2)0.0013 (19)
C300.018 (2)0.017 (2)0.020 (2)0.0005 (16)0.0001 (16)0.0003 (16)
Geometric parameters (Å, º) top
Br1—C81.948 (4)C14—C151.389 (6)
Br2—C231.947 (4)C14—H140.9500
O1—C71.209 (5)C15—H150.9500
O2—C91.209 (5)C16—C171.388 (6)
O3—C241.207 (5)C16—C211.398 (6)
O4—C221.204 (5)C16—C221.491 (6)
C1—C21.390 (6)C17—C181.387 (6)
C1—C61.391 (6)C17—H170.9500
C1—C71.489 (6)C18—C191.369 (6)
C2—C31.389 (6)C18—H180.9500
C2—H20.9500C19—C201.399 (7)
C3—C41.369 (6)C19—H190.9500
C3—H30.9500C20—C211.386 (6)
C4—C51.393 (6)C20—H200.9500
C4—H40.9500C21—H210.9500
C5—C61.389 (6)C22—C231.545 (6)
C5—H50.9500C23—C241.518 (6)
C6—H60.9500C23—H231.0000
C7—C81.544 (6)C24—C251.498 (6)
C8—C91.538 (5)C25—C301.370 (6)
C8—H81.0000C25—C261.400 (6)
C9—C101.487 (6)C26—C271.389 (6)
C10—C151.391 (6)C26—H260.9500
C10—C111.405 (6)C27—C281.393 (6)
C11—C121.377 (6)C27—H270.9500
C11—H110.9500C28—C291.390 (6)
C12—C131.390 (6)C28—H280.9500
C12—H120.9500C29—C301.379 (6)
C13—C141.384 (6)C29—H290.9500
C13—H130.9500C30—H300.9500
C2—C1—C6119.6 (4)C17—C16—C21120.3 (4)
C2—C1—C7122.7 (4)C17—C16—C22123.0 (4)
C6—C1—C7117.7 (3)C21—C16—C22116.7 (4)
C3—C2—C1119.7 (4)C18—C17—C16119.3 (4)
C3—C2—H2120.2C18—C17—H17120.4
C1—C2—H2120.2C16—C17—H17120.4
C4—C3—C2121.0 (4)C19—C18—C17120.7 (5)
C4—C3—H3119.5C19—C18—H18119.7
C2—C3—H3119.5C17—C18—H18119.7
C3—C4—C5119.7 (4)C18—C19—C20120.7 (5)
C3—C4—H4120.2C18—C19—H19119.6
C5—C4—H4120.2C20—C19—H19119.6
C6—C5—C4120.0 (4)C21—C20—C19119.0 (4)
C6—C5—H5120.0C21—C20—H20120.5
C4—C5—H5120.0C19—C20—H20120.5
C5—C6—C1120.0 (4)C20—C21—C16120.0 (4)
C5—C6—H6120.0C20—C21—H21120.0
C1—C6—H6120.0C16—C21—H21120.0
O1—C7—C1121.6 (4)O4—C22—C16121.9 (4)
O1—C7—C8120.8 (4)O4—C22—C23117.5 (4)
C1—C7—C8117.6 (3)C16—C22—C23120.5 (4)
C9—C8—C7109.2 (3)C24—C23—C22108.4 (3)
C9—C8—Br1108.2 (3)C24—C23—Br2111.3 (3)
C7—C8—Br1109.6 (3)C22—C23—Br2105.9 (3)
C9—C8—H8110.0C24—C23—H23110.4
C7—C8—H8110.0C22—C23—H23110.4
Br1—C8—H8110.0Br2—C23—H23110.4
O2—C9—C10121.3 (4)O3—C24—C25120.7 (4)
O2—C9—C8118.4 (4)O3—C24—C23122.0 (4)
C10—C9—C8120.3 (3)C25—C24—C23117.2 (3)
C15—C10—C11119.5 (4)C30—C25—C26119.3 (4)
C15—C10—C9122.8 (4)C30—C25—C24118.8 (4)
C11—C10—C9117.7 (3)C26—C25—C24121.8 (4)
C12—C11—C10120.1 (4)C27—C26—C25120.4 (4)
C12—C11—H11120.0C27—C26—H26119.8
C10—C11—H11120.0C25—C26—H26119.8
C11—C12—C13120.4 (4)C26—C27—C28119.4 (4)
C11—C12—H12119.8C26—C27—H27120.3
C13—C12—H12119.8C28—C27—H27120.3
C14—C13—C12119.6 (4)C29—C28—C27119.9 (4)
C14—C13—H13120.2C29—C28—H28120.1
C12—C13—H13120.2C27—C28—H28120.1
C13—C14—C15120.8 (4)C30—C29—C28119.9 (4)
C13—C14—H14119.6C30—C29—H29120.0
C15—C14—H14119.6C28—C29—H29120.0
C14—C15—C10119.6 (4)C25—C30—C29121.1 (4)
C14—C15—H15120.2C25—C30—H30119.4
C10—C15—H15120.2C29—C30—H30119.4
C6—C1—C2—C33.2 (6)C21—C16—C17—C181.4 (7)
C7—C1—C2—C3175.0 (4)C22—C16—C17—C18179.5 (4)
C1—C2—C3—C42.2 (6)C16—C17—C18—C191.7 (8)
C2—C3—C4—C50.1 (7)C17—C18—C19—C201.5 (9)
C3—C4—C5—C61.3 (7)C18—C19—C20—C211.1 (8)
C4—C5—C6—C10.3 (6)C19—C20—C21—C160.8 (7)
C2—C1—C6—C51.9 (6)C17—C16—C21—C201.0 (7)
C7—C1—C6—C5176.4 (4)C22—C16—C21—C20179.9 (4)
C2—C1—C7—O1172.5 (4)C17—C16—C22—O4173.4 (4)
C6—C1—C7—O15.7 (6)C21—C16—C22—O47.5 (6)
C2—C1—C7—C86.3 (6)C17—C16—C22—C237.3 (6)
C6—C1—C7—C8175.4 (4)C21—C16—C22—C23171.9 (4)
O1—C7—C8—C9101.3 (5)O4—C22—C23—C2415.6 (5)
C1—C7—C8—C977.6 (5)C16—C22—C23—C24165.0 (4)
O1—C7—C8—Br117.1 (5)O4—C22—C23—Br2103.9 (4)
C1—C7—C8—Br1164.1 (3)C16—C22—C23—Br275.4 (4)
C7—C8—C9—O26.1 (5)C22—C23—C24—O3107.7 (5)
Br1—C8—C9—O2113.1 (4)Br2—C23—C24—O38.4 (6)
C7—C8—C9—C10175.3 (3)C22—C23—C24—C2568.5 (5)
Br1—C8—C9—C1065.5 (4)Br2—C23—C24—C25175.4 (3)
O2—C9—C10—C15168.2 (4)O3—C24—C25—C305.6 (7)
C8—C9—C10—C1513.3 (6)C23—C24—C25—C30170.6 (4)
O2—C9—C10—C1110.7 (6)O3—C24—C25—C26178.3 (4)
C8—C9—C10—C11167.9 (4)C23—C24—C25—C265.5 (6)
C15—C10—C11—C121.2 (6)C30—C25—C26—C271.2 (6)
C9—C10—C11—C12177.8 (4)C24—C25—C26—C27174.9 (4)
C10—C11—C12—C130.6 (7)C25—C26—C27—C280.2 (6)
C11—C12—C13—C140.2 (7)C26—C27—C28—C292.1 (6)
C12—C13—C14—C150.3 (7)C27—C28—C29—C302.6 (7)
C13—C14—C15—C100.3 (6)C26—C25—C30—C290.7 (7)
C11—C10—C15—C141.0 (6)C24—C25—C30—C29175.5 (4)
C9—C10—C15—C14177.9 (4)C28—C29—C30—C251.2 (7)

Experimental details

Crystal data
Chemical formulaC15H11BrO2
Mr303.15
Crystal system, space groupOrthorhombic, Pca21
Temperature (K)100
a, b, c (Å)28.0680 (6), 5.6508 (1), 15.3741 (3)
V3)2438.43 (8)
Z8
Radiation typeMo Kα
µ (mm1)3.36
Crystal size (mm)0.27 × 0.20 × 0.06
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.464, 0.824
No. of measured, independent and
observed [I > 2σ(I)] reflections
21610, 5562, 4774
Rint0.060
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.087, 0.99
No. of reflections5562
No. of parameters325
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.76, 0.52
Absolute structureFlack (1983), 2644 Fridel pairs
Absolute structure parameter0.002 (9)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

 

Acknowledgements

We thank the University of Malaya for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals
First citationKaitner, B. & Meštrović, E. (1993). Acta Cryst. C49, 1523–1525.  CSD CrossRef CAS Web of Science IUCr Journals
First citationOzturk, S., Akkurt, M. & Ide, S. (1997). Z. Kristallogr. 212, 808–810.  CAS
First citationRobert, J. F. & Panouse, J. J. (1979). J. Heterocycl. Chem. 16, 1201–1207.  CrossRef CAS
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWestrip, S. P. (2008). publCIF. In preparation.

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