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Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296

4-Chloro-N-(4-cyano-2-nitro­phenyl)-3-nitro­benz­amide

aDepartment of Chemistry, University of York, Heslington, York YO10 5DD, England
*Correspondence e-mail: l.cronin@ed.ac.uk

(Received 28 June 1999; accepted 11 November 1999)

The structure of the title compound, C14H7ClN4O5, comprises two nearly coplanar phenyl rings connected via an amido moiety.

Comment

In the course of an investigation of the effect of water on the fluoro­denitration of substituted benzo­nitriles, it was observed that hydro­lysis of the –CN moiety was possible. In an attempted fluorination of 4-chloro-3-nitro­benzo­nitrile, the title compound, (I[link]), was observed as a previously uncharacterized product in such reactions (Adams et al., 1999[Adams, D. A., Clark, J. H., McFarland, H. & Nightingale, D. J. (1999). J. Fluorine Chem. 94, 51-54.]).

[Scheme 1]

In (I[link]) (Fig. 1[link]), the amido unit is planar with an O3—C8—N3—H3 torsion angle of 171 (2)°. However, the C10—C9—C8—O3 and C4—C5—N3—C8 torsion angles of 22.3 (4) and −28.0 (4)°, respectively, indicate significant deviation from planarity with the amido group. In the chlorine-containing ring, the nitro group is twisted out of the plane of the phenyl ring [the O4—N4—C11—C10 torsion angle is 53.3 (4)°]. This is presumably due to the steric clash between the Cl atom and nitro group. In contrast, the nitro group ortho to the amido group on the other phenyl ring is more coplanar with the ring [the O2—N2—C6—C5 torsion angle is −14.5 (4)°]. This conformation may be stabilized, at least in part, by a hydrogen-bond interaction between the N—H of the amido group and an O atom of the nitro group [N3⋯O2 2.662 (5), N3—H3⋯O2 2.06 (3) Å and N3—H3⋯O2 125 (3)°]. The planes of the phenyl rings are inclined to each other at an angle of 3.2 (3)°. Examination of the packing of the mol­ecules reveals a head-to-tail phenyl–phenyl interaction between adjacently stacked mol­ecules of 3.77 (1) Å, indicating a weak intermolecular π-stacking interaction.

[Figure 1]
Figure 1
View of (I[link]) showing the atom-numbering scheme and ellipsoids at the 50% probability level.

Experimental

4-Chloro-3-nitro­benzo­nitrile (0.182 g, 1 mmol) was placed in a round-bottomed flask. Di­methyl sulfoxide (10 ml, distilled and stored under argon) was added and the solution heated to 353 K under argon. Tetra­methyl­ammonium fluoride (0.20 g, 1.70 mmol; TMAF·[4 \over 3]H2O, prepared by drying the tetrahydrate under vacuum at 333 K for 2 d) was added to the solution. After 1 h, the reaction mixture was cooled in an ice bath. The organics were extracted into ether, washed well with water, dried (magnesium sulfate) and the ether removed on a rotary evaporator. The crude mixture was then recrystallized from aceto­nitrile to give yellow needles (Adams et al., 1999[Adams, D. A., Clark, J. H., McFarland, H. & Nightingale, D. J. (1999). J. Fluorine Chem. 94, 51-54.]).

Crystal data
  • C14H7ClN4O5

  • Mr = 346.69

  • Triclinic, [P\overline 1]

  • a = 7.804 (13) Å

  • b = 12.931 (6) Å

  • c = 7.49 (4) Å

  • α = 91.59 (16)°

  • β = 112.9 (2)°

  • γ = 88.12 (8)°

  • V = 695 (4) Å3

  • Z = 2

  • Dx = 1.656 Mg m−3

  • Mo Kα radiation

  • Cell parameters from 20 reflections

  • θ = 9–15°

  • μ = 0.312 mm−1

  • T = 293 (2) K

  • Needle, yellow

  • 0.55 × 0.20 × 0.20 mm

Data collection
  • Rigaku four-circle AFC-6 diffractometer

  • ω–2θ scans

  • Absorption correction: empirical via ψ scans (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.782, Tmax = 0.940

  • 2453 measured reflections

  • 2453 independent reflections

  • 1747 reflections with I > 2σ(I)

  • θmax = 25.03°

  • h = 0 → 9

  • k = −15 → 15

  • l = −8 → 8

  • 3 standard reflections every 150 reflections intensity variation: 0.5%

Refinement
  • Refinement on F2

  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.145

  • S = 1.053

  • 2452 reflections

  • 220 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • w = 1/[σ2(Fo2) + (0.0735P)2 + 0.1533P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max = 0.001

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.31 e Å−3

Table 1
Selected geometric parameters (Å, °)

Cl1—C12 1.724 (3)
O1—N2 1.225 (4)
O2—N2 1.234 (3)
N3—C8 1.377 (5)
N3—C5 1.409 (4)
O4—N4 1.213 (5)
O5—N4 1.219 (6)
N1—C1 1.147 (4)
N2—C6 1.465 (4)
O3—C8 1.210 (4)
N4—C11 1.472 (4)
C1—C2 1.445 (4)
C8—N3—C5 125.4 (3)
O1—N2—O2 122.5 (2)
O1—N2—C6 118.3 (2)
O2—N2—C6 119.2 (2)
O4—N4—O5 124.9 (3)
O4—N4—C11 117.3 (3)
O5—N4—C11 117.7 (3)
N1—C1—C2 177.8 (3)
O3—C8—N3 123.9 (3)
O3—C8—C9 121.1 (3)
N3—C8—C9 114.9 (3)

The H atom on N3 was located in a difference Fourier synthesis. It was allowed to refine positionally with Uiso = 1.2Ueq(N3). The phenyl H atoms were placed geometrically and thereafter refined using a riding model with Uiso(H) = 1.2Ueq(C).

Data collection: TEXSAN (Molecular Structure Corporation, 1993[Molecular Structure Corporation (1993). TEXSAN. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.]); cell refinement: TEXSAN; data reduction: TEXSAN; program(s) used to solve structure: SHELXS86 (Sheldrick, 1985[Sheldrick, G. M. (1985). SHELXS86. Crystallographic Computing 3, edited by G. M. Sheldrick, C. Krüger & R. Goddard, pp. 175-189. Oxford University Press.]); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993[Sheldrick, G. M. (1993). SHELXL93. University of Göttingen, Germany.]); molecular graphics: ORTEP (Johnson, 1965[Johnson, C. K. (1965). ORTEP. Report ORNL-3794. Oak Ridge National Laboratory, Tennessee, USA.]); software used to prepare material for publication: SHELXL93.

Supporting information


Comment top

In the course of an investigation of the effect of water on the fluorodenitration of substituted benzonitriles, it was observed that hydrolysis of the –CN moiety was possible. In an attempted fluorination of 4-chloro-3-nitrobenzonitrile, the title compound, (I), was observed as a previously uncharacterized product in such reactions (Adams et al., 1999).

In (I) (Fig. 1), the amido unit is planar with an O3—C8—N3—H3A torsion angle of 171 (2)°. However, the C10—C9—C8—O3 and C4—C5—N3—C8 torsion angles of 22.3 (4) and −28.0 (4)°, respectively, indicate significant deviation from planarity with the amido group. In the chlorine-containing ring, the nitro group is twisted out of the plane of the phenyl ring [the O4—N4—C11—C10 torsion angle is 53.3 (4)°]. This is presumably due to the steric clash between the Cl atom and nitro group. In contrast, the nitro group ortho to the amido group on the other phenyl ring is more coplanar with the ring [the O2—N2—C6—C5 torsion angle is −14.5 (4)°]. This conformation may be stabilized, at least in part, by a hydrogen-bond interaction between the N—H of the amido group and an O atom of the nitro group [N3···O2 2.662 (5) Å, N3—H3A···O2 2.06 (3) Å and N3—H3A···O2 125 (3)°]. The planes of the phenyl rings are inclined to each other at an angle of 3.2 (3)°. Examination of the packing of the molecules reveals a head-to-tail phenyl–phenyl interaction between adjacently stacked molecules of 3.77 (1) Å, indicating a weak intermolecular π-stacking interaction.

Experimental top

4-Chloro-3-nitrobenzonitrile (0.182 g, 1 mmol) was placed in a round-bottomed flask. Dimethyl sulfoxide (10 ml, distilled and stored under argon) was added and the solution heated to 353 K under argon. Tetramethylammonium fluoride (0.20 g, 1.70 mmol; TMAF.4/3H2O, prepared by drying the tetrahydrate under vacuum at 333 K for 2 d) was added to the solution. After 1 h the reaction mixture was cooled in an ice bath. The organics were extracted into ether and washed well with water, dried (magnesium sulfate) and the ether removed on a rotary evaporator. The crude mixture was then recrystallized from acetonitrile to give yellow needles (Adams et al., 1999).

Refinement top

The H atom on N3 was located in a difference Fourier synthesis. It was allowed to refine positionally with Uiso = 1.2Ueq(N3). The phenyl H atoms were placed geometrically and thereafter refined using a riding model with Uiso(H) = 1.2Ueq(C)

Computing details top

Data collection: TEXSAN (Molecular Structure Corporation, 1993); cell refinement: TEXSAN; data reduction: TEXSAN; program(s) used to solve structure: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: ORTEP (Johnson, 1965); software used to prepare material for publication: SHELXL93.

Figures top
[Figure 1] Fig. 1. View of (I) showing the atom-numbering scheme and ellipsoids at the 50% probability level.
4-Chloro-N-(4-cyano-2-nitrophenyl)-3-nitrobenzamide top
Crystal data top
C14H7ClN4O5Z = 2
Mr = 346.69F(000) = 352
Triclinic, P1Dx = 1.656 Mg m3
a = 7.804 (13) ÅMo Kα radiation, λ = 0.71069 Å
b = 12.931 (6) ÅCell parameters from 20 reflections
c = 7.49 (4) Åθ = 9–15°
α = 91.59 (16)°µ = 0.31 mm1
β = 112.9 (2)°T = 293 K
γ = 88.12 (8)°Needle, yellow
V = 695 (4) Å30.55 × 0.2 × 0.2 mm
Data collection top
Rigaku four-circle AFC6
diffractometer
1747 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 2.8°
Graphite monochromatorh = 09
ω–2θ scansk = 1515
Absorption correction: empirical (using intensity measurements) via ψ scans (north et al., 1968)
?
l = 88
Tmin = 0.782, Tmax = 0.9403 standard reflections every 150 reflections
2453 measured reflections intensity decay: variation 0.5%
2453 independent 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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0735P)2 + 0.1533P]
where P = (Fo2 + 2Fc2)/3
2452 reflections(Δ/σ)max = 0.001
220 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.31 e Å3
Crystal data top
C14H7ClN4O5γ = 88.12 (8)°
Mr = 346.69V = 695 (4) Å3
Triclinic, P1Z = 2
a = 7.804 (13) ÅMo Kα radiation
b = 12.931 (6) ŵ = 0.31 mm1
c = 7.49 (4) ÅT = 293 K
α = 91.59 (16)°0.55 × 0.2 × 0.2 mm
β = 112.9 (2)°
Data collection top
Rigaku four-circle AFC6
diffractometer
2453 independent reflections
Absorption correction: empirical (using intensity measurements) via ψ scans (north et al., 1968)
?
1747 reflections with I > 2σ(I)
Tmin = 0.782, Tmax = 0.9403 standard reflections every 150 reflections
2453 measured reflections intensity decay: variation 0.5%
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.145H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.24 e Å3
2452 reflectionsΔρmin = 0.31 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. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating R factor obs 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
Cl10.72328 (11)0.44652 (6)0.42411 (13)0.0512 (3)
O10.1103 (3)0.1416 (2)0.0668 (3)0.0491 (6)
O20.0890 (3)0.02284 (14)0.2026 (3)0.0420 (5)
N30.4317 (3)0.0462 (2)0.2098 (4)0.0355 (6)
H3A0.342 (4)0.000 (3)0.183 (5)0.043*
O41.0909 (3)0.2578 (2)0.3301 (4)0.0663 (7)
O51.0947 (3)0.3336 (2)0.5918 (4)0.0673 (8)
N10.2131 (4)0.5540 (2)0.0408 (5)0.0554 (8)
N20.0499 (3)0.1114 (2)0.1366 (3)0.0323 (5)
O30.7448 (3)0.0701 (2)0.3766 (3)0.0476 (6)
N41.0199 (3)0.2826 (2)0.4435 (4)0.0395 (6)
C10.2418 (4)0.4673 (2)0.0663 (5)0.0393 (7)
C20.2846 (4)0.3588 (2)0.0977 (4)0.0320 (6)
C30.4616 (4)0.3275 (2)0.1227 (4)0.0370 (7)
H30.5493 (4)0.3762 (2)0.1161 (4)0.044*
C40.5077 (4)0.2251 (2)0.1570 (4)0.0345 (7)
H40.6258 (4)0.2052 (2)0.1710 (4)0.041*
C50.3797 (4)0.1504 (2)0.1712 (4)0.0294 (6)
C60.1997 (3)0.1832 (2)0.1383 (4)0.0276 (6)
C70.1522 (4)0.2861 (2)0.1031 (4)0.0318 (6)
H70.0327 (4)0.3063 (2)0.0832 (4)0.038*
C80.6100 (4)0.0128 (2)0.3105 (4)0.0308 (6)
C90.6280 (3)0.1029 (2)0.3345 (4)0.0289 (6)
C100.8037 (4)0.1412 (2)0.3704 (4)0.0308 (6)
H100.9006 (4)0.0967 (2)0.3731 (4)0.037*
C110.8316 (3)0.2456 (2)0.4015 (4)0.0301 (6)
C120.6897 (4)0.3150 (2)0.3955 (4)0.0312 (6)
C130.5151 (4)0.2765 (2)0.3598 (4)0.0361 (7)
H130.4180 (4)0.3214 (2)0.3554 (4)0.043*
C140.4857 (4)0.1714 (2)0.3307 (4)0.0318 (6)
H140.3687 (4)0.1462 (2)0.3082 (4)0.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0491 (5)0.0239 (4)0.0773 (6)0.0052 (3)0.0208 (4)0.0003 (3)
O10.0259 (11)0.0422 (12)0.079 (2)0.0052 (9)0.0198 (11)0.0050 (11)
O20.0403 (12)0.0245 (10)0.0609 (14)0.0026 (8)0.0197 (10)0.0075 (9)
N30.0268 (12)0.0234 (12)0.054 (2)0.0042 (9)0.0134 (11)0.0017 (11)
O40.0384 (13)0.094 (2)0.074 (2)0.0077 (13)0.0292 (13)0.0130 (15)
O50.0384 (13)0.0551 (15)0.089 (2)0.0173 (11)0.0040 (13)0.0209 (14)
N10.047 (2)0.0302 (15)0.088 (2)0.0057 (12)0.0249 (15)0.0093 (14)
N20.0298 (13)0.0288 (13)0.0395 (14)0.0009 (10)0.0148 (10)0.0015 (10)
O30.0301 (11)0.0308 (11)0.0652 (15)0.0013 (9)0.0010 (10)0.0040 (10)
N40.0279 (13)0.0341 (14)0.053 (2)0.0061 (10)0.0114 (12)0.0050 (12)
C10.035 (2)0.028 (2)0.056 (2)0.0021 (12)0.0180 (14)0.0045 (13)
C20.036 (2)0.0237 (14)0.035 (2)0.0040 (11)0.0134 (12)0.0028 (11)
C30.035 (2)0.0287 (14)0.046 (2)0.0013 (12)0.0148 (13)0.0037 (12)
C40.0243 (14)0.0316 (15)0.048 (2)0.0046 (11)0.0142 (13)0.0042 (12)
C50.0290 (14)0.0259 (13)0.032 (2)0.0044 (11)0.0103 (11)0.0004 (11)
C60.0259 (13)0.0256 (13)0.0306 (14)0.0018 (10)0.0103 (11)0.0009 (11)
C70.0316 (15)0.0267 (14)0.038 (2)0.0061 (11)0.0140 (12)0.0020 (11)
C80.0268 (14)0.0288 (14)0.037 (2)0.0055 (11)0.0128 (12)0.0018 (12)
C90.0270 (14)0.0275 (14)0.0308 (15)0.0037 (11)0.0096 (11)0.0003 (11)
C100.0243 (14)0.0298 (14)0.038 (2)0.0001 (11)0.0125 (12)0.0007 (12)
C110.0238 (14)0.0304 (14)0.035 (2)0.0056 (11)0.0104 (12)0.0029 (12)
C120.0318 (15)0.0243 (14)0.036 (2)0.0036 (11)0.0113 (12)0.0006 (11)
C130.0274 (15)0.034 (2)0.048 (2)0.0040 (12)0.0152 (13)0.0031 (13)
C140.0246 (14)0.0300 (14)0.041 (2)0.0045 (11)0.0125 (12)0.0029 (12)
Geometric parameters (Å, º) top
Cl1—C121.724 (3)C2—C31.392 (4)
O1—N21.225 (4)C3—C41.374 (4)
O2—N21.234 (3)C4—C51.399 (4)
N3—C81.377 (5)C5—C61.406 (4)
N3—C51.409 (4)C6—C71.383 (4)
O4—N41.213 (5)C8—C91.506 (4)
O5—N41.219 (6)C9—C141.390 (4)
N1—C11.147 (4)C9—C101.396 (4)
N2—C61.465 (4)C10—C111.373 (4)
O3—C81.210 (4)C11—C121.390 (4)
N4—C111.472 (4)C12—C131.389 (4)
C1—C21.445 (4)C13—C141.382 (4)
C2—C71.385 (4)
C8—N3—C5125.4 (3)C5—C6—N2122.6 (2)
O1—N2—O2122.5 (2)C6—C7—C2119.2 (3)
O1—N2—C6118.3 (2)O3—C8—N3123.9 (3)
O2—N2—C6119.2 (2)O3—C8—C9121.1 (3)
O4—N4—O5124.9 (3)N3—C8—C9114.9 (3)
O4—N4—C11117.3 (3)C14—C9—C10119.1 (3)
O5—N4—C11117.7 (3)C14—C9—C8124.7 (2)
N1—C1—C2177.8 (3)C10—C9—C8116.2 (2)
C7—C2—C3119.9 (3)C11—C10—C9119.2 (3)
C7—C2—C1120.9 (3)C10—C11—C12122.2 (2)
C3—C2—C1119.2 (3)C10—C11—N4117.5 (2)
C4—C3—C2120.5 (3)C12—C11—N4120.3 (3)
C3—C4—C5120.9 (3)C13—C12—C11118.4 (3)
C4—C5—C6117.4 (2)C13—C12—Cl1119.7 (2)
C4—C5—N3119.8 (3)C11—C12—Cl1121.9 (2)
C6—C5—N3122.7 (2)C14—C13—C12120.0 (3)
C7—C6—C5121.8 (3)C13—C14—C9121.1 (3)
C7—C6—N2115.6 (2)

Experimental details

Crystal data
Chemical formulaC14H7ClN4O5
Mr346.69
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)7.804 (13), 12.931 (6), 7.49 (4)
α, β, γ (°)91.59 (16), 112.9 (2), 88.12 (8)
V3)695 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.31
Crystal size (mm)0.55 × 0.2 × 0.2
Data collection
DiffractometerRigaku four-circle AFC6
diffractometer
Absorption correctionEmpirical (using intensity measurements) via ψ scans (North et al., 1968)
Tmin, Tmax0.782, 0.940
No. of measured, independent and
observed [I > 2σ(I)] reflections
2453, 2453, 1747
Rint?
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.145, 1.05
No. of reflections2452
No. of parameters220
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.24, 0.31

Computer programs: TEXSAN (Molecular Structure Corporation, 1993), TEXSAN, SHELXS86 (Sheldrick, 1985), SHELXL93 (Sheldrick, 1993), ORTEP (Johnson, 1965), SHELXL93.

Selected geometric parameters (Å, º) top
Cl1—C121.724 (3)O5—N41.219 (6)
O1—N21.225 (4)N1—C11.147 (4)
O2—N21.234 (3)N2—C61.465 (4)
N3—C81.377 (5)O3—C81.210 (4)
N3—C51.409 (4)N4—C111.472 (4)
O4—N41.213 (5)C1—C21.445 (4)
C8—N3—C5125.4 (3)O5—N4—C11117.7 (3)
O1—N2—O2122.5 (2)N1—C1—C2177.8 (3)
O1—N2—C6118.3 (2)O3—C8—N3123.9 (3)
O2—N2—C6119.2 (2)O3—C8—C9121.1 (3)
O4—N4—O5124.9 (3)N3—C8—C9114.9 (3)
O4—N4—C11117.3 (3)
 

Footnotes

Current address: Department of Chemistry, University of Edinburgh, West Mains Road, Edinburgh EH9 1NH, Scotland.

Acknowledgements

We thank Victrex plc for financial support (to DA), the EPSRC Clean Technology Unit for a studentship (to DN) and the Royal Academy of Engineering/EPSRC for a Clean Technology Fellowship (to JHC).

References

First citationAdams, D. A., Clark, J. H., McFarland, H. & Nightingale, D. J. (1999). J. Fluorine Chem. 94, 51–54.  Web of Science CrossRef CAS Google Scholar
First citationJohnson, C. K. (1965). ORTEP. Report ORNL-3794. Oak Ridge National Laboratory, Tennessee, USA.  Google Scholar
First citationMolecular Structure Corporation (1993). TEXSAN. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.  Google Scholar
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science Google Scholar
First citationSheldrick, G. M. (1985). SHELXS86. Crystallographic Computing 3, edited by G. M. Sheldrick, C. Krüger & R. Goddard, pp. 175–189. Oxford University Press.  Google Scholar
First citationSheldrick, G. M. (1993). SHELXL93. University of Göttingen, Germany.  Google Scholar

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