organic compounds
5-(3,5-Difluorophenyl)-1-(4-fluorophenyl)-3-trifluoromethyl-1H-pyrazole
aDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, bDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, and cDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore, India
*Correspondence e-mail: drsreenivasa@yahoo.co.in
In the title compound, C16H8F6N2, the dihedral angle between the pyrazole and difluorobenzene rings is 50.30 (13)°, while those between the pyrazole and fluorobenzene rings and between the difluorobenzene and fluorobenzene rings are 38.56 (13) and 53.50 (11)°, respectively. Aromatic π–π stacking interactions between adjacent difluorobenzene rings [centroid–centroid separation = 3.6082 (11) Å] link the molecules into dimers parallel to [21-2].
CCDC reference: 974623
Related literature
For background to pyrazole derivatives and their uses, see: Ramaiah et al. (1999). For a similar structure, see: Sreenivasa et al. (2013).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2009); cell SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97.
Supporting information
CCDC reference: 974623
https://doi.org/10.1107/S1600536813032650/wm2788sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813032650/wm2788Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536813032650/wm2788Isup3.cml
1-(3,5-Difluorophenyl)-4,4,4-trifluorobutane-1,3-dione (0.015 mmol) and (4-fluorophenyl)hydrazine (0.015 mmol) were taken in dry ethanol (14 ml) and the reaction mixture was stirred for 6 h at 348 K under a nitrogen atmosphere. The reaction was monitored by TLC and the excess solvent was removed by vacuum to obtain the crude compound. It was purified by
using dichloromethane and ethanol (9:1) as eluent.Yellow prisms suitable for diffraction studies were grown by slow evaporation of the solvent system: dichloromethane and methanol (9:1).
The H atoms were positioned with idealized geometry using a riding model with C—H = 0.93 Å. The isotropic displacement parameters for all H atoms were set to 1.2 times Ueq of the parent atom.
The pyrazole entity is an important moiety in numerous natural and synthetic compounds and in medicinal chemistry (see, for example: Ramaiah et al., 1999). As part of our studies in this area, the title compound, C16H8F6N2, was synthesized and its
determined.In the title compound, the dihedral angle between the pyrazole and the difluorobenzene rings is 50.30 (13)°, while those between the pyrazole and the fluorobenzene rings and the difluorobenzene and the fluorobenzene rings are, respectively, 38.56 (13)° and 53.50 (11)°. Compared to these values, the dihedral angles between the pyrazole-benzoic acid ring, pyrazole-fluorobenzene ring and fluorobenzene-benzoic acid ring in the structure of the related compound 2-[5-(2-fluorophenyl)-3-isobutyl-1H-pyrazol-1-yl]benzoic acid (Sreenivasa et al., 2013) are 53.1 (1)°, 52.1 (1)° and 62.1 (1)°, respectively. Aromatic π–π stacking interactions between the difluorobenzene rings in the title structure [centroid-to-centroid separation = 3.6082 (11) Å] links the molecules parallel to [212] in the (Fig 2).
For background to pyrazole derivatives and their uses, see: Ramaiah et al. (1999). For a similar structure, see: Sreenivasa et al. (2013).
Data collection: APEX2 (Bruker, 2009); cell
SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C16H8F6N2 | F(000) = 344 |
Mr = 342.24 | Prism |
Triclinic, P1 | Dx = 1.650 Mg m−3 |
Hall symbol: -P 1 | Melting point: 456 K |
a = 7.2535 (3) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 8.6686 (4) Å | Cell parameters from 1234 reflections |
c = 11.7690 (5) Å | θ = 4.0–64.8° |
α = 70.909 (1)° | µ = 1.39 mm−1 |
β = 80.139 (1)° | T = 293 K |
γ = 88.077 (1)° | Prism, yellow |
V = 688.78 (5) Å3 | 0.39 × 0.35 × 0.29 mm |
Z = 2 |
Bruker APEXII CCD diffractometer | 2181 independent reflections |
Radiation source: fine-focus sealed tube | 2040 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
φ and ω scans | θmax = 64.8°, θmin = 4.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −8→8 |
Tmin = 0.611, Tmax = 0.669 | k = −9→10 |
7069 measured reflections | l = −13→13 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.181 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.1212P)2 + 0.5142P] where P = (Fo2 + 2Fc2)/3 |
2181 reflections | (Δ/σ)max < 0.001 |
217 parameters | Δρmax = 0.45 e Å−3 |
0 restraints | Δρmin = −0.48 e Å−3 |
C16H8F6N2 | γ = 88.077 (1)° |
Mr = 342.24 | V = 688.78 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.2535 (3) Å | Cu Kα radiation |
b = 8.6686 (4) Å | µ = 1.39 mm−1 |
c = 11.7690 (5) Å | T = 293 K |
α = 70.909 (1)° | 0.39 × 0.35 × 0.29 mm |
β = 80.139 (1)° |
Bruker APEXII CCD diffractometer | 2181 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 2040 reflections with I > 2σ(I) |
Tmin = 0.611, Tmax = 0.669 | Rint = 0.042 |
7069 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.181 | H-atom parameters constrained |
S = 1.11 | Δρmax = 0.45 e Å−3 |
2181 reflections | Δρmin = −0.48 e Å−3 |
217 parameters |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > 2σ(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. |
x | y | z | Uiso*/Ueq | ||
F5 | 0.4695 (2) | 0.16122 (18) | 0.61518 (14) | 0.0259 (4) | |
F4 | 0.0082 (2) | 0.5540 (2) | 0.60896 (14) | 0.0277 (4) | |
F3 | 0.8754 (2) | 1.09529 (19) | 0.57955 (14) | 0.0311 (4) | |
F2 | 0.8448 (2) | 1.0637 (2) | 0.77056 (15) | 0.0338 (5) | |
F6 | 0.7353 (3) | −0.0365 (2) | 1.12881 (15) | 0.0368 (5) | |
F1 | 1.0813 (2) | 0.9640 (2) | 0.68380 (16) | 0.0329 (5) | |
N2 | 0.7064 (3) | 0.5860 (3) | 0.80633 (18) | 0.0181 (5) | |
C8 | 0.7111 (3) | 0.4265 (3) | 0.8934 (2) | 0.0178 (6) | |
C2 | 0.5326 (3) | 0.3904 (3) | 0.6683 (2) | 0.0186 (6) | |
H2 | 0.6510 | 0.3520 | 0.6815 | 0.022* | |
C10 | 0.5548 (4) | 0.1787 (3) | 1.0287 (2) | 0.0231 (6) | |
H10 | 0.4464 | 0.1152 | 1.0651 | 0.028* | |
C7 | 0.6008 (3) | 0.6408 (3) | 0.7159 (2) | 0.0178 (5) | |
C3 | 0.4110 (4) | 0.3037 (3) | 0.6324 (2) | 0.0188 (5) | |
C14 | 0.7893 (3) | 0.8337 (3) | 0.7149 (2) | 0.0191 (6) | |
C4 | 0.2343 (3) | 0.3540 (3) | 0.6116 (2) | 0.0196 (6) | |
H4 | 0.1552 | 0.2928 | 0.5875 | 0.024* | |
C5 | 0.1808 (3) | 0.5007 (3) | 0.6286 (2) | 0.0196 (6) | |
N1 | 0.8244 (3) | 0.7042 (3) | 0.80627 (19) | 0.0197 (5) | |
C16 | 0.8973 (3) | 0.9877 (3) | 0.6872 (2) | 0.0222 (6) | |
C11 | 0.7271 (4) | 0.1186 (3) | 1.0535 (2) | 0.0252 (6) | |
C6 | 0.2943 (3) | 0.5943 (3) | 0.6650 (2) | 0.0191 (6) | |
H6 | 0.2529 | 0.6918 | 0.6763 | 0.023* | |
C1 | 0.4720 (3) | 0.5386 (3) | 0.6844 (2) | 0.0174 (5) | |
C13 | 0.8827 (4) | 0.3653 (3) | 0.9218 (2) | 0.0230 (6) | |
H13 | 0.9914 | 0.4288 | 0.8860 | 0.028* | |
C15 | 0.6500 (3) | 0.8044 (3) | 0.6551 (2) | 0.0187 (6) | |
H15 | 0.6018 | 0.8771 | 0.5902 | 0.022* | |
C9 | 0.5463 (3) | 0.3358 (3) | 0.9483 (2) | 0.0207 (6) | |
H9 | 0.4315 | 0.3799 | 0.9314 | 0.025* | |
C12 | 0.8922 (4) | 0.2094 (4) | 1.0036 (2) | 0.0276 (6) | |
H12 | 1.0060 | 0.1672 | 1.0243 | 0.033* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F5 | 0.0287 (8) | 0.0245 (8) | 0.0340 (9) | 0.0044 (6) | −0.0110 (6) | −0.0196 (7) |
F4 | 0.0148 (7) | 0.0429 (10) | 0.0349 (9) | 0.0067 (6) | −0.0103 (6) | −0.0230 (8) |
F3 | 0.0322 (9) | 0.0291 (9) | 0.0316 (9) | −0.0068 (7) | −0.0084 (7) | −0.0073 (7) |
F2 | 0.0414 (10) | 0.0309 (9) | 0.0371 (10) | −0.0063 (7) | −0.0009 (7) | −0.0241 (8) |
F6 | 0.0465 (10) | 0.0285 (10) | 0.0311 (9) | −0.0012 (8) | −0.0096 (8) | −0.0021 (7) |
F1 | 0.0195 (8) | 0.0299 (9) | 0.0533 (11) | −0.0036 (6) | −0.0088 (7) | −0.0169 (8) |
N2 | 0.0154 (10) | 0.0240 (12) | 0.0198 (11) | −0.0024 (8) | −0.0037 (8) | −0.0131 (9) |
C8 | 0.0225 (12) | 0.0211 (13) | 0.0150 (11) | −0.0015 (10) | −0.0050 (9) | −0.0116 (10) |
C2 | 0.0149 (11) | 0.0263 (14) | 0.0191 (12) | 0.0019 (10) | −0.0053 (9) | −0.0125 (10) |
C10 | 0.0284 (13) | 0.0241 (14) | 0.0184 (13) | −0.0058 (10) | 0.0013 (10) | −0.0113 (11) |
C7 | 0.0135 (11) | 0.0257 (13) | 0.0197 (12) | 0.0001 (9) | −0.0044 (9) | −0.0140 (10) |
C3 | 0.0215 (12) | 0.0192 (12) | 0.0195 (12) | 0.0013 (9) | −0.0033 (9) | −0.0116 (10) |
C14 | 0.0180 (12) | 0.0240 (13) | 0.0197 (12) | −0.0010 (10) | −0.0027 (9) | −0.0135 (11) |
C4 | 0.0178 (12) | 0.0267 (14) | 0.0180 (12) | −0.0040 (10) | −0.0036 (9) | −0.0114 (10) |
C5 | 0.0115 (11) | 0.0315 (14) | 0.0173 (12) | 0.0010 (10) | −0.0032 (9) | −0.0098 (10) |
N1 | 0.0175 (10) | 0.0232 (12) | 0.0227 (11) | −0.0031 (8) | −0.0043 (8) | −0.0127 (9) |
C16 | 0.0202 (12) | 0.0267 (14) | 0.0246 (14) | 0.0011 (10) | −0.0054 (10) | −0.0140 (11) |
C11 | 0.0373 (16) | 0.0224 (14) | 0.0167 (12) | 0.0003 (11) | −0.0061 (11) | −0.0067 (10) |
C6 | 0.0182 (12) | 0.0235 (13) | 0.0194 (12) | 0.0025 (10) | −0.0047 (9) | −0.0116 (10) |
C1 | 0.0157 (11) | 0.0241 (13) | 0.0159 (12) | −0.0018 (9) | −0.0030 (9) | −0.0108 (10) |
C13 | 0.0214 (13) | 0.0283 (14) | 0.0219 (13) | −0.0032 (10) | −0.0057 (10) | −0.0103 (11) |
C15 | 0.0182 (12) | 0.0215 (13) | 0.0208 (12) | 0.0022 (10) | −0.0059 (9) | −0.0116 (10) |
C9 | 0.0180 (12) | 0.0303 (14) | 0.0192 (12) | 0.0001 (10) | −0.0018 (9) | −0.0157 (11) |
C12 | 0.0278 (14) | 0.0321 (15) | 0.0258 (14) | 0.0027 (11) | −0.0109 (11) | −0.0105 (12) |
F5—C3 | 1.359 (3) | C7—C15 | 1.390 (4) |
F4—C5 | 1.351 (3) | C7—C1 | 1.478 (3) |
F3—C16 | 1.336 (3) | C3—C4 | 1.376 (4) |
F2—C16 | 1.349 (3) | C14—N1 | 1.329 (3) |
F6—C11 | 1.353 (3) | C14—C15 | 1.399 (3) |
F1—C16 | 1.339 (3) | C14—C16 | 1.483 (3) |
N2—N1 | 1.357 (3) | C4—C5 | 1.383 (4) |
N2—C7 | 1.367 (3) | C4—H4 | 0.9300 |
N2—C8 | 1.430 (3) | C5—C6 | 1.383 (3) |
C8—C13 | 1.388 (4) | C11—C12 | 1.385 (4) |
C8—C9 | 1.390 (4) | C6—C1 | 1.390 (3) |
C2—C3 | 1.378 (3) | C6—H6 | 0.9300 |
C2—C1 | 1.404 (4) | C13—C12 | 1.387 (4) |
C2—H2 | 0.9300 | C13—H13 | 0.9300 |
C10—C11 | 1.378 (4) | C15—H15 | 0.9300 |
C10—C9 | 1.387 (4) | C9—H9 | 0.9300 |
C10—H10 | 0.9300 | C12—H12 | 0.9300 |
N1—N2—C7 | 112.0 (2) | F3—C16—F1 | 107.1 (2) |
N1—N2—C8 | 118.73 (19) | F3—C16—F2 | 106.1 (2) |
C7—N2—C8 | 129.3 (2) | F1—C16—F2 | 106.02 (19) |
C13—C8—C9 | 121.0 (2) | F3—C16—C14 | 111.8 (2) |
C13—C8—N2 | 118.7 (2) | F1—C16—C14 | 112.6 (2) |
C9—C8—N2 | 120.3 (2) | F2—C16—C14 | 112.7 (2) |
C3—C2—C1 | 117.9 (2) | F6—C11—C10 | 118.5 (2) |
C3—C2—H2 | 121.1 | F6—C11—C12 | 118.7 (2) |
C1—C2—H2 | 121.1 | C10—C11—C12 | 122.8 (3) |
C11—C10—C9 | 118.7 (2) | C5—C6—C1 | 118.2 (2) |
C11—C10—H10 | 120.6 | C5—C6—H6 | 120.9 |
C9—C10—H10 | 120.6 | C1—C6—H6 | 120.9 |
N2—C7—C15 | 106.9 (2) | C6—C1—C2 | 120.5 (2) |
N2—C7—C1 | 125.3 (2) | C6—C1—C7 | 119.4 (2) |
C15—C7—C1 | 127.6 (2) | C2—C1—C7 | 120.0 (2) |
F5—C3—C4 | 118.0 (2) | C12—C13—C8 | 120.0 (2) |
F5—C3—C2 | 118.2 (2) | C12—C13—H13 | 120.0 |
C4—C3—C2 | 123.8 (2) | C8—C13—H13 | 120.0 |
N1—C14—C15 | 113.4 (2) | C7—C15—C14 | 103.6 (2) |
N1—C14—C16 | 118.8 (2) | C7—C15—H15 | 128.2 |
C15—C14—C16 | 127.8 (2) | C14—C15—H15 | 128.2 |
C3—C4—C5 | 116.2 (2) | C10—C9—C8 | 119.3 (2) |
C3—C4—H4 | 121.9 | C10—C9—H9 | 120.3 |
C5—C4—H4 | 121.9 | C8—C9—H9 | 120.3 |
F4—C5—C4 | 117.9 (2) | C11—C12—C13 | 118.0 (2) |
F4—C5—C6 | 118.7 (2) | C11—C12—H12 | 121.0 |
C4—C5—C6 | 123.4 (2) | C13—C12—H12 | 121.0 |
C14—N1—N2 | 104.07 (19) | ||
N1—N2—C8—C13 | −37.8 (3) | C9—C10—C11—F6 | −177.9 (2) |
C7—N2—C8—C13 | 139.9 (2) | C9—C10—C11—C12 | 1.4 (4) |
N1—N2—C8—C9 | 142.0 (2) | F4—C5—C6—C1 | −179.7 (2) |
C7—N2—C8—C9 | −40.3 (3) | C4—C5—C6—C1 | 0.7 (4) |
N1—N2—C7—C15 | −1.2 (3) | C5—C6—C1—C2 | −0.6 (4) |
C8—N2—C7—C15 | −179.0 (2) | C5—C6—C1—C7 | 176.2 (2) |
N1—N2—C7—C1 | 174.1 (2) | C3—C2—C1—C6 | 0.3 (4) |
C8—N2—C7—C1 | −3.7 (4) | C3—C2—C1—C7 | −176.5 (2) |
C1—C2—C3—F5 | 179.2 (2) | N2—C7—C1—C6 | 134.5 (2) |
C1—C2—C3—C4 | 0.0 (4) | C15—C7—C1—C6 | −51.2 (3) |
F5—C3—C4—C5 | −179.2 (2) | N2—C7—C1—C2 | −48.6 (3) |
C2—C3—C4—C5 | 0.0 (4) | C15—C7—C1—C2 | 125.7 (3) |
C3—C4—C5—F4 | 180.0 (2) | C9—C8—C13—C12 | 1.8 (4) |
C3—C4—C5—C6 | −0.4 (4) | N2—C8—C13—C12 | −178.4 (2) |
C15—C14—N1—N2 | 0.5 (3) | N2—C7—C15—C14 | 1.4 (2) |
C16—C14—N1—N2 | −179.3 (2) | C1—C7—C15—C14 | −173.8 (2) |
C7—N2—N1—C14 | 0.5 (2) | N1—C14—C15—C7 | −1.2 (3) |
C8—N2—N1—C14 | 178.55 (19) | C16—C14—C15—C7 | 178.5 (2) |
N1—C14—C16—F3 | 167.2 (2) | C11—C10—C9—C8 | 1.3 (3) |
C15—C14—C16—F3 | −12.5 (3) | C13—C8—C9—C10 | −2.9 (3) |
N1—C14—C16—F1 | 46.5 (3) | N2—C8—C9—C10 | 177.3 (2) |
C15—C14—C16—F1 | −133.1 (3) | F6—C11—C12—C13 | 176.8 (2) |
N1—C14—C16—F2 | −73.3 (3) | C10—C11—C12—C13 | −2.4 (4) |
C15—C14—C16—F2 | 107.0 (3) | C8—C13—C12—C11 | 0.8 (4) |
Experimental details
Crystal data | |
Chemical formula | C16H8F6N2 |
Mr | 342.24 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 7.2535 (3), 8.6686 (4), 11.7690 (5) |
α, β, γ (°) | 70.909 (1), 80.139 (1), 88.077 (1) |
V (Å3) | 688.78 (5) |
Z | 2 |
Radiation type | Cu Kα |
µ (mm−1) | 1.39 |
Crystal size (mm) | 0.39 × 0.35 × 0.29 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.611, 0.669 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7069, 2181, 2040 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.587 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.181, 1.11 |
No. of reflections | 2181 |
No. of parameters | 217 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.45, −0.48 |
Computer programs: APEX2 (Bruker, 2009), SAINT-Plus (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008).
Acknowledgements
The authors acknowledge the IOE X-ray diffractometer Facility, University of Mysore, Mysore, for the data collection.
References
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Sreenivasa, S., Manojkumar, K. E., Suchetan, P. A., Mohan, N. R., Kumar, V. & Palakshamurthy, B. S. (2013). Acta Cryst. E69, o176. CSD CrossRef IUCr Journals Google Scholar
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The pyrazole entity is an important moiety in numerous natural and synthetic compounds and in medicinal chemistry (see, for example: Ramaiah et al., 1999). As part of our studies in this area, the title compound, C16H8F6N2, was synthesized and its crystal structure determined.
In the title compound, the dihedral angle between the pyrazole and the difluorobenzene rings is 50.30 (13)°, while those between the pyrazole and the fluorobenzene rings and the difluorobenzene and the fluorobenzene rings are, respectively, 38.56 (13)° and 53.50 (11)°. Compared to these values, the dihedral angles between the pyrazole-benzoic acid ring, pyrazole-fluorobenzene ring and fluorobenzene-benzoic acid ring in the structure of the related compound 2-[5-(2-fluorophenyl)-3-isobutyl-1H-pyrazol-1-yl]benzoic acid (Sreenivasa et al., 2013) are 53.1 (1)°, 52.1 (1)° and 62.1 (1)°, respectively. Aromatic π–π stacking interactions between the difluorobenzene rings in the title structure [centroid-to-centroid separation = 3.6082 (11) Å] links the molecules parallel to [212] in the crystal structure (Fig 2).