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ISSN: 2056-9890

Benzil bis­­(ketazine)

aDepartment of Chemistry, Vijaygarh Jyotish Ray College, 8/2 Vijaygarh, Jadavpur, Kolkata 32, India, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 24 June 2009; accepted 25 June 2009; online 4 July 2009)

The title compound (systematic name: 1,1′,2,2′-tetra­phenyl-2,2′-azinodiethanone), C28H20N2O2, was obtained by the reaction of benzil monohydrazone with chromium(III) nitrate. The dibenzyl­idene hydrazine unit is nearly planar (r.m.s. deviation = 0.073 Å) and the two benzoyl units are oriented almost perpendicular to it [dihedral angle = 87.81 (2), 87.81 (2)°]. The mol­ecules are linked into chains along the c axis by C—H⋯O hydrogen bonds and the chains are cross-linked via C—H⋯π inter­actions involving the benzoyl phenyl rings.

Related literature

For the synthesis of title compound using copper bis­(acetyl­acetonate) as catalyst, see: Ibata & Singh (1994[Ibata, T. & Singh, G. S. (1994). Tetrahedron Lett. 35, 2581-2584.]); Singh (1983[Singh, S. B. (1983). Indian J. Chem. Sect. B, 20, 810.]).

[Scheme 1]

Experimental

Crystal data
  • C28H20N2O2

  • Mr = 416.46

  • Monoclinic, P 21 /c

  • a = 8.2875 (2) Å

  • b = 22.1023 (4) Å

  • c = 11.6602 (2) Å

  • β = 97.539 (1)°

  • V = 2117.37 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 140 K

  • 0.30 × 0.04 × 0.03 mm

Data collection
  • Bruker SMART APEX area-detector diffractometer

  • Absorption correction: none

  • 17323 measured reflections

  • 4857 independent reflections

  • 3510 reflections with I > 2σ(I)

  • Rint = 0.030

Refinement
  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.107

  • S = 1.03

  • 4857 reflections

  • 289 parameters

  • H-atom parameters constrained

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C1—H1⋯O1i 0.95 2.24 3.0832 (16) 147
C13—H13⋯Cg1ii 0.95 2.68 3.5705 (16) 157
C18—H18⋯Cg2iii 0.95 2.66 3.5304 (16) 153
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) x+1, y, z; (iii) x-1, y, z. Cg1 and Cg2 are centroids of the C1–C6 and C23–C28 rings, respectively.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

For the synthesis of title compound using copper bis(acetylacetonate) as catalyst, see: Ibata & Singh (1994); Singh (1983). Cg1 and Cg2 are centroids of the C1–C6 and C23–C28 rings, respectively

Experimental top

Benzil monohydrazone (0.224 g, 1 mmol) was dissolved in acetonitrile (20 ml) and to this was added chromium nitrate nonahyrate (0.40 g, 1 mmol). The greenish yellowish mixture was stirred at room temperature for 6 h. Bright yellow prisms were collected in 40% yield.

Refinement top

H-atoms were placed in calculated positions (C-H = 0.95 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2Ueq(C).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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, 2009).

Figures top
[Figure 1] Fig. 1. Displacement ellipsoid plot (Barbour, 2001) of C28H20N2O2 at the 70% probability level; H atoms are drawn as spheres of arbitrary radius.
1,1',2,2'-tetraphenyl-2,2'-azinodiethanone top
Crystal data top
C28H20N2O2F(000) = 872
Mr = 416.46Dx = 1.306 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3878 reflections
a = 8.2875 (2) Åθ = 2.5–27.9°
b = 22.1023 (4) ŵ = 0.08 mm1
c = 11.6602 (2) ÅT = 140 K
β = 97.539 (1)°Prism, yellow
V = 2117.37 (7) Å30.30 × 0.04 × 0.03 mm
Z = 4
Data collection top
Bruker SMART APEX area-detector
diffractometer
3510 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
Graphite monochromatorθmax = 27.5°, θmin = 1.8°
ω scansh = 1010
17323 measured reflectionsk = 2827
4857 independent reflectionsl = 1515
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0486P)2 + 0.4715P]
where P = (Fo2 + 2Fc2)/3
4857 reflections(Δ/σ)max = 0.001
289 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C28H20N2O2V = 2117.37 (7) Å3
Mr = 416.46Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.2875 (2) ŵ = 0.08 mm1
b = 22.1023 (4) ÅT = 140 K
c = 11.6602 (2) Å0.30 × 0.04 × 0.03 mm
β = 97.539 (1)°
Data collection top
Bruker SMART APEX area-detector
diffractometer
3510 reflections with I > 2σ(I)
17323 measured reflectionsRint = 0.030
4857 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.107H-atom parameters constrained
S = 1.03Δρmax = 0.24 e Å3
4857 reflectionsΔρmin = 0.21 e Å3
289 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.37058 (13)0.75630 (5)0.13158 (8)0.0366 (3)
O20.17265 (13)0.56277 (5)0.47749 (8)0.0336 (3)
N10.34699 (13)0.66169 (5)0.33697 (11)0.0257 (3)
N20.18382 (13)0.66513 (5)0.28286 (10)0.0252 (3)
C10.27649 (16)0.81384 (6)0.40407 (11)0.0215 (3)
H10.32940.78350.45310.026*
C20.20231 (17)0.86230 (7)0.45113 (13)0.0303 (3)
H20.20430.86530.53260.036*
C30.12519 (19)0.90640 (7)0.37938 (15)0.0377 (4)
H30.07440.93970.41180.045*
C40.12170 (19)0.90223 (7)0.26063 (15)0.0370 (4)
H40.06780.93250.21190.044*
C50.19592 (17)0.85447 (6)0.21267 (13)0.0278 (3)
H50.19450.85200.13120.033*
C60.27335 (15)0.80970 (6)0.28467 (11)0.0198 (3)
C70.35415 (15)0.75841 (6)0.23347 (11)0.0219 (3)
C80.42829 (16)0.70877 (6)0.31371 (11)0.0211 (3)
C90.59933 (16)0.71554 (6)0.36520 (11)0.0211 (3)
C100.66251 (18)0.67959 (7)0.45829 (13)0.0318 (3)
H100.59490.65040.48810.038*
C110.82226 (18)0.68586 (7)0.50792 (14)0.0349 (4)
H110.86390.66120.57170.042*
C120.92181 (17)0.72815 (7)0.46459 (13)0.0296 (3)
H121.03190.73240.49850.036*
C130.86090 (17)0.76404 (7)0.37219 (13)0.0312 (3)
H130.92940.79290.34220.037*
C140.70016 (17)0.75823 (6)0.32287 (12)0.0267 (3)
H140.65860.78350.25990.032*
C150.10218 (16)0.61745 (6)0.30204 (11)0.0215 (3)
C160.06870 (16)0.61175 (6)0.24937 (11)0.0215 (3)
C170.16874 (17)0.56676 (6)0.28567 (13)0.0279 (3)
H170.12740.53980.34600.033*
C180.32831 (18)0.56134 (7)0.23374 (14)0.0327 (3)
H180.39610.53060.25860.039*
C190.38917 (17)0.60026 (7)0.14627 (13)0.0307 (3)
H190.49870.59620.11100.037*
C200.29147 (17)0.64511 (7)0.10965 (13)0.0302 (3)
H200.33380.67200.04950.036*
C210.13179 (17)0.65073 (6)0.16090 (12)0.0269 (3)
H210.06460.68150.13550.032*
C220.17830 (16)0.56479 (6)0.37387 (11)0.0222 (3)
C230.25313 (16)0.51611 (6)0.31005 (12)0.0215 (3)
C240.34362 (17)0.47038 (7)0.37097 (13)0.0299 (3)
H240.35540.46970.45310.036*
C250.4161 (2)0.42613 (7)0.31128 (15)0.0372 (4)
H250.48000.39560.35280.045*
C260.39637 (19)0.42599 (7)0.19180 (14)0.0344 (4)
H260.44590.39520.15160.041*
C270.30485 (18)0.47042 (7)0.13063 (13)0.0309 (3)
H270.29030.47000.04840.037*
C280.23428 (17)0.51564 (6)0.18982 (12)0.0242 (3)
H280.17250.54660.14780.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0392 (6)0.0513 (7)0.0191 (5)0.0020 (5)0.0023 (4)0.0069 (5)
O20.0389 (6)0.0379 (6)0.0238 (5)0.0007 (5)0.0037 (4)0.0048 (4)
N10.0177 (6)0.0207 (6)0.0374 (7)0.0007 (4)0.0007 (5)0.0034 (5)
N20.0167 (6)0.0214 (6)0.0366 (7)0.0006 (4)0.0000 (5)0.0056 (5)
C10.0188 (6)0.0230 (6)0.0220 (7)0.0012 (5)0.0003 (5)0.0008 (5)
C20.0244 (7)0.0341 (8)0.0317 (8)0.0013 (6)0.0009 (6)0.0103 (6)
C30.0286 (8)0.0273 (8)0.0549 (11)0.0056 (6)0.0034 (7)0.0120 (7)
C40.0334 (8)0.0229 (7)0.0501 (10)0.0023 (6)0.0119 (7)0.0057 (7)
C50.0265 (7)0.0266 (7)0.0278 (7)0.0057 (6)0.0051 (6)0.0066 (6)
C60.0162 (6)0.0200 (6)0.0227 (7)0.0044 (5)0.0004 (5)0.0012 (5)
C70.0171 (6)0.0267 (7)0.0206 (6)0.0055 (5)0.0017 (5)0.0039 (5)
C80.0199 (7)0.0202 (6)0.0230 (7)0.0002 (5)0.0026 (5)0.0061 (5)
C90.0187 (6)0.0207 (6)0.0238 (7)0.0006 (5)0.0018 (5)0.0055 (5)
C100.0245 (7)0.0319 (8)0.0380 (8)0.0049 (6)0.0002 (6)0.0069 (6)
C110.0291 (8)0.0367 (8)0.0363 (8)0.0007 (6)0.0058 (7)0.0049 (7)
C120.0178 (7)0.0347 (8)0.0350 (8)0.0014 (6)0.0014 (6)0.0115 (6)
C130.0231 (7)0.0346 (8)0.0358 (8)0.0082 (6)0.0029 (6)0.0029 (6)
C140.0244 (7)0.0276 (7)0.0275 (7)0.0033 (6)0.0010 (6)0.0008 (6)
C150.0206 (7)0.0192 (6)0.0252 (7)0.0008 (5)0.0045 (5)0.0066 (5)
C160.0197 (6)0.0192 (6)0.0261 (7)0.0010 (5)0.0045 (5)0.0064 (5)
C170.0244 (7)0.0256 (7)0.0332 (8)0.0025 (6)0.0025 (6)0.0012 (6)
C180.0242 (7)0.0331 (8)0.0413 (9)0.0104 (6)0.0064 (6)0.0038 (7)
C190.0185 (7)0.0386 (8)0.0343 (8)0.0021 (6)0.0002 (6)0.0102 (6)
C200.0254 (7)0.0341 (8)0.0300 (8)0.0014 (6)0.0004 (6)0.0013 (6)
C210.0232 (7)0.0257 (7)0.0320 (8)0.0030 (6)0.0041 (6)0.0009 (6)
C220.0180 (6)0.0241 (7)0.0240 (7)0.0051 (5)0.0013 (5)0.0032 (5)
C230.0186 (6)0.0189 (6)0.0270 (7)0.0030 (5)0.0027 (5)0.0001 (5)
C240.0288 (8)0.0319 (8)0.0295 (8)0.0032 (6)0.0060 (6)0.0076 (6)
C250.0386 (9)0.0268 (8)0.0485 (10)0.0117 (7)0.0140 (8)0.0129 (7)
C260.0374 (9)0.0232 (7)0.0455 (9)0.0040 (6)0.0166 (7)0.0017 (6)
C270.0326 (8)0.0313 (8)0.0295 (8)0.0000 (6)0.0063 (6)0.0050 (6)
C280.0238 (7)0.0221 (7)0.0264 (7)0.0009 (5)0.0016 (6)0.0000 (5)
Geometric parameters (Å, º) top
O1—C71.2143 (16)C13—H130.95
O2—C221.2160 (16)C14—H140.95
N1—C81.2878 (17)C15—C161.4733 (18)
N1—N21.4173 (15)C15—C221.5216 (19)
N2—C151.2877 (17)C16—C211.3922 (19)
C1—C21.3839 (19)C16—C171.3955 (19)
C1—C61.3920 (18)C17—C181.385 (2)
C1—H10.95C17—H170.95
C2—C31.385 (2)C18—C191.378 (2)
C2—H20.95C18—H180.95
C3—C41.384 (2)C19—C201.383 (2)
C3—H30.95C19—H190.95
C4—C51.377 (2)C20—C211.384 (2)
C4—H40.95C20—H200.95
C5—C61.3980 (18)C21—H210.95
C5—H50.95C22—C231.4890 (18)
C6—C71.4814 (18)C23—C281.3902 (19)
C7—C81.5185 (18)C23—C241.3959 (19)
C8—C91.4727 (18)C24—C251.383 (2)
C9—C101.3908 (19)C24—H240.95
C9—C141.3929 (19)C25—C261.381 (2)
C10—C111.380 (2)C25—H250.95
C10—H100.95C26—C271.381 (2)
C11—C121.385 (2)C26—H260.95
C11—H110.95C27—C281.3869 (19)
C12—C131.379 (2)C27—H270.95
C12—H120.95C28—H280.95
C13—C141.386 (2)
C8—N1—N2110.97 (11)C9—C14—H14119.9
C15—N2—N1111.78 (11)N2—C15—C16119.72 (12)
C2—C1—C6119.77 (13)N2—C15—C22122.16 (12)
C2—C1—H1120.1C16—C15—C22118.06 (11)
C6—C1—H1120.1C21—C16—C17119.04 (12)
C1—C2—C3119.93 (14)C21—C16—C15120.20 (12)
C1—C2—H2120.0C17—C16—C15120.75 (12)
C3—C2—H2120.0C18—C17—C16120.00 (14)
C4—C3—C2120.32 (14)C18—C17—H17120.0
C4—C3—H3119.8C16—C17—H17120.0
C2—C3—H3119.8C19—C18—C17120.34 (13)
C5—C4—C3120.37 (14)C19—C18—H18119.8
C5—C4—H4119.8C17—C18—H18119.8
C3—C4—H4119.8C18—C19—C20120.25 (13)
C4—C5—C6119.54 (14)C18—C19—H19119.9
C4—C5—H5120.2C20—C19—H19119.9
C6—C5—H5120.2C19—C20—C21119.76 (14)
C1—C6—C5120.06 (13)C19—C20—H20120.1
C1—C6—C7120.21 (12)C21—C20—H20120.1
C5—C6—C7119.71 (12)C20—C21—C16120.61 (13)
O1—C7—C6122.57 (13)C20—C21—H21119.7
O1—C7—C8119.13 (12)C16—C21—H21119.7
C6—C7—C8118.18 (11)O2—C22—C23122.88 (13)
N1—C8—C9119.89 (12)O2—C22—C15120.51 (12)
N1—C8—C7122.21 (12)C23—C22—C15116.58 (11)
C9—C8—C7117.89 (11)C28—C23—C24119.31 (12)
C10—C9—C14118.78 (12)C28—C23—C22120.68 (12)
C10—C9—C8120.25 (12)C24—C23—C22120.01 (12)
C14—C9—C8120.96 (12)C25—C24—C23119.74 (14)
C11—C10—C9120.80 (14)C25—C24—H24120.1
C11—C10—H10119.6C23—C24—H24120.1
C9—C10—H10119.6C26—C25—C24120.49 (14)
C10—C11—C12119.94 (14)C26—C25—H25119.8
C10—C11—H11120.0C24—C25—H25119.8
C12—C11—H11120.0C25—C26—C27120.26 (14)
C13—C12—C11119.90 (13)C25—C26—H26119.9
C13—C12—H12120.0C27—C26—H26119.9
C11—C12—H12120.0C26—C27—C28119.63 (14)
C12—C13—C14120.27 (14)C26—C27—H27120.2
C12—C13—H13119.9C28—C27—H27120.2
C14—C13—H13119.9C23—C28—C27120.55 (13)
C13—C14—C9120.30 (13)C23—C28—H28119.7
C13—C14—H14119.9C27—C28—H28119.7
C8—N1—N2—C15177.82 (12)N1—N2—C15—C16177.87 (11)
C6—C1—C2—C30.1 (2)N1—N2—C15—C220.55 (17)
C1—C2—C3—C40.1 (2)N2—C15—C16—C2113.52 (19)
C2—C3—C4—C50.5 (2)C22—C15—C16—C21163.92 (12)
C3—C4—C5—C60.8 (2)N2—C15—C16—C17167.62 (13)
C2—C1—C6—C50.20 (19)C22—C15—C16—C1714.95 (18)
C2—C1—C6—C7179.23 (12)C21—C16—C17—C180.1 (2)
C4—C5—C6—C10.6 (2)C15—C16—C17—C18178.82 (13)
C4—C5—C6—C7179.66 (12)C16—C17—C18—C190.1 (2)
C1—C6—C7—O1171.53 (13)C17—C18—C19—C200.1 (2)
C5—C6—C7—O17.51 (19)C18—C19—C20—C210.2 (2)
C1—C6—C7—C84.51 (18)C19—C20—C21—C160.2 (2)
C5—C6—C7—C8176.45 (12)C17—C16—C21—C200.1 (2)
N2—N1—C8—C9177.59 (11)C15—C16—C21—C20178.98 (12)
N2—N1—C8—C72.72 (17)N2—C15—C22—O291.73 (16)
O1—C7—C8—N193.45 (16)C16—C15—C22—O290.91 (15)
C6—C7—C8—N190.38 (15)N2—C15—C22—C2390.28 (15)
O1—C7—C8—C986.25 (15)C16—C15—C22—C2387.09 (14)
C6—C7—C8—C989.92 (14)O2—C22—C23—C28169.79 (13)
N1—C8—C9—C1015.03 (19)C15—C22—C23—C288.15 (18)
C7—C8—C9—C10165.26 (12)O2—C22—C23—C2410.4 (2)
N1—C8—C9—C14165.69 (13)C15—C22—C23—C24171.70 (12)
C7—C8—C9—C1414.01 (18)C28—C23—C24—C251.4 (2)
C14—C9—C10—C110.2 (2)C22—C23—C24—C25178.43 (13)
C8—C9—C10—C11179.45 (13)C23—C24—C25—C261.6 (2)
C9—C10—C11—C120.3 (2)C24—C25—C26—C270.5 (2)
C10—C11—C12—C130.2 (2)C25—C26—C27—C280.7 (2)
C11—C12—C13—C140.4 (2)C24—C23—C28—C270.2 (2)
C12—C13—C14—C90.8 (2)C22—C23—C28—C27179.65 (13)
C10—C9—C14—C130.7 (2)C26—C27—C28—C230.9 (2)
C8—C9—C14—C13179.97 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O1i0.952.243.0832 (16)147
C13—H13···Cg1ii0.952.683.5705 (16)157
C18—H18···Cg2iii0.952.663.5304 (16)153
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x+1, y, z; (iii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC28H20N2O2
Mr416.46
Crystal system, space groupMonoclinic, P21/c
Temperature (K)140
a, b, c (Å)8.2875 (2), 22.1023 (4), 11.6602 (2)
β (°) 97.539 (1)
V3)2117.37 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.30 × 0.04 × 0.03
Data collection
DiffractometerBruker SMART APEX area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
17323, 4857, 3510
Rint0.030
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.107, 1.03
No. of reflections4857
No. of parameters289
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.21

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O1i0.952.243.0832 (16)147
C13—H13···Cg1ii0.952.683.5705 (16)157
C18—H18···Cg2iii0.952.663.5304 (16)153
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x+1, y, z; (iii) x1, y, z.
 

Acknowledgements

The authors thank Vijaygarh Jyotish Ray College and the University of Malaya for supporting this study.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationIbata, T. & Singh, G. S. (1994). Tetrahedron Lett. 35, 2581–2584.  CrossRef CAS Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSingh, S. B. (1983). Indian J. Chem. Sect. B, 20, 810.  Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

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