organic compounds
5-Bromo-2,4,6-trimethyl-3-(4-methylphenylsulfinyl)-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
In the title compound, C18H17BrO2S, the dihedral angle between the methylphenyl ring and the mean plane of the benzofuran rung system is 87.0 (2)°. In the crystal, molecules related by inversion are paired into dimers via C—H⋯O and C—H⋯π interactions. These dimers are further linked by C—H⋯O hydrogen bonds and π–π interactions between the benzene and furan rings of neighbouring molecules [centroid–centroid distance = 3.555 (5) Å], resulting in a three-dimensional supramolecular network.
CCDC reference: 988674
Related literature
For background information and the crystal structures of related compounds, see: Choi et al. (2008, 2011).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.
Supporting information
CCDC reference: 988674
10.1107/S1600536814004310/xu5773sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814004310/xu5773Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814004310/xu5773Isup3.cml
3-Chloroperoxybenzoic acid (77%, 224 mg, 1.0 mmol) was added in small portions to a stirred solution of 5-bromo-2,4,6-trimethyl-3-(4-methylphenylsulfanyl)-1-benzofuran (325 mg, 0.9 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
(hexane–ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 69%, m.p. 470–471 K; Rf = 0.51 (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 ethyl acetate at room temperature.All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aryl and 0.98 Å for methyl H atoms. Uiso(H) = 1.2Ueq(C) for aryl and 1.5Ueq(C) for methyl H atoms. The positions of methyl hydrogens were optimized rotationally. The highest peak in the difference map is 0.88 Å from BR1 and the deepest hole is 0.95 Å from BR1.
Data collection: APEX2 (Bruker, 2009); cell
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 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).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. | |
Fig. 2. A view of the C—H···O, C—H···π and π···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, z; (ii) - x + 1, - y + 2, - z + 2; (iii) - x + 1, - y + 1, - z + 2; (iv) x - 1, y, z.] |
C18H17BrO2S | Z = 2 |
Mr = 377.29 | F(000) = 384 |
Triclinic, P1 | Dx = 1.538 Mg m−3 |
Hall symbol: -P 1 | Melting point = 470–471 K |
a = 8.793 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.229 (5) Å | Cell parameters from 5866 reflections |
c = 10.861 (6) Å | θ = 2.2–28.2° |
α = 86.105 (16)° | µ = 2.66 mm−1 |
β = 69.582 (17)° | T = 173 K |
γ = 80.550 (16)° | Block, colourless |
V = 814.7 (8) Å3 | 0.42 × 0.35 × 0.23 mm |
Bruker SMART APEXII CCD diffractometer | 2857 independent reflections |
Radiation source: rotating anode | 2420 reflections with I > 2σ(I) |
Graphite multilayer monochromator | Rint = 0.067 |
Detector resolution: 10.0 pixels mm-1 | θmax = 25.0°, θmin = 2.0° |
ϕ and ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | k = −10→10 |
Tmin = 0.402, Tmax = 0.580 | l = −12→12 |
10322 measured reflections |
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)] = 0.062 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.177 | H-atom parameters constrained |
S = 1.15 | w = 1/[σ2(Fo2) + (0.0949P)2 + 1.1374P] where P = (Fo2 + 2Fc2)/3 |
2857 reflections | (Δ/σ)max = 0.001 |
203 parameters | Δρmax = 1.44 e Å−3 |
0 restraints | Δρmin = −1.27 e Å−3 |
C18H17BrO2S | γ = 80.550 (16)° |
Mr = 377.29 | V = 814.7 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.793 (5) Å | Mo Kα radiation |
b = 9.229 (5) Å | µ = 2.66 mm−1 |
c = 10.861 (6) Å | T = 173 K |
α = 86.105 (16)° | 0.42 × 0.35 × 0.23 mm |
β = 69.582 (17)° |
Bruker SMART APEXII CCD diffractometer | 2857 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 2420 reflections with I > 2σ(I) |
Tmin = 0.402, Tmax = 0.580 | Rint = 0.067 |
10322 measured reflections |
R[F2 > 2σ(F2)] = 0.062 | 0 restraints |
wR(F2) = 0.177 | H-atom parameters constrained |
S = 1.15 | Δρmax = 1.44 e Å−3 |
2857 reflections | Δρmin = −1.27 e Å−3 |
203 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.73930 (7) | 0.37481 (6) | 0.59473 (5) | 0.0546 (3) | |
S1 | 0.14037 (13) | 0.83306 (15) | 0.96038 (13) | 0.0394 (3) | |
O1 | 0.5385 (4) | 0.7754 (3) | 1.0502 (3) | 0.0328 (7) | |
O2 | 0.0597 (5) | 0.7075 (5) | 0.9495 (4) | 0.0571 (11) | |
C1 | 0.3381 (5) | 0.7704 (5) | 0.9688 (5) | 0.0319 (10) | |
C2 | 0.4792 (5) | 0.6678 (5) | 0.8932 (4) | 0.0276 (9) | |
C3 | 0.5165 (6) | 0.5721 (5) | 0.7880 (5) | 0.0346 (10) | |
C4 | 0.6773 (6) | 0.4989 (5) | 0.7443 (5) | 0.0346 (10) | |
C5 | 0.7984 (6) | 0.5111 (5) | 0.7983 (5) | 0.0360 (11) | |
C6 | 0.7561 (5) | 0.6025 (5) | 0.9048 (5) | 0.0346 (11) | |
H6 | 0.8326 | 0.6129 | 0.9463 | 0.042* | |
C7 | 0.5984 (5) | 0.6779 (5) | 0.9481 (4) | 0.0278 (9) | |
C8 | 0.3796 (5) | 0.8293 (5) | 1.0595 (4) | 0.0307 (10) | |
C9 | 0.3914 (7) | 0.5491 (7) | 0.7294 (6) | 0.0503 (14) | |
H9A | 0.4179 | 0.5943 | 0.6416 | 0.075* | |
H9B | 0.2824 | 0.5945 | 0.7855 | 0.075* | |
H9C | 0.3921 | 0.4436 | 0.7229 | 0.075* | |
C10 | 0.9707 (6) | 0.4268 (7) | 0.7463 (6) | 0.0520 (14) | |
H10A | 1.0319 | 0.4439 | 0.8028 | 0.078* | |
H10B | 1.0265 | 0.4603 | 0.6566 | 0.078* | |
H10C | 0.9653 | 0.3216 | 0.7459 | 0.078* | |
C11 | 0.2953 (7) | 0.9413 (6) | 1.1636 (5) | 0.0447 (12) | |
H11A | 0.3449 | 1.0314 | 1.1384 | 0.067* | |
H11B | 0.3071 | 0.9033 | 1.2468 | 0.067* | |
H11C | 0.1786 | 0.9629 | 1.1742 | 0.067* | |
C12 | 0.1975 (5) | 0.9215 (5) | 0.8030 (5) | 0.0353 (11) | |
C13 | 0.1410 (6) | 0.8845 (6) | 0.7076 (6) | 0.0413 (12) | |
H13 | 0.0813 | 0.8043 | 0.7215 | 0.050* | |
C14 | 0.1720 (7) | 0.9653 (6) | 0.5911 (5) | 0.0450 (12) | |
H14 | 0.1340 | 0.9392 | 0.5250 | 0.054* | |
C15 | 0.2570 (7) | 1.0826 (6) | 0.5702 (5) | 0.0459 (13) | |
C16 | 0.3127 (7) | 1.1186 (6) | 0.6677 (6) | 0.0485 (14) | |
H16 | 0.3734 | 1.1980 | 0.6538 | 0.058* | |
C17 | 0.2810 (6) | 1.0405 (6) | 0.7841 (5) | 0.0414 (12) | |
H17 | 0.3162 | 1.0681 | 0.8513 | 0.050* | |
C18 | 0.2899 (11) | 1.1726 (8) | 0.4462 (6) | 0.075 (2) | |
H18A | 0.3956 | 1.1316 | 0.3821 | 0.112* | |
H18B | 0.2933 | 1.2741 | 0.4653 | 0.112* | |
H18C | 0.2025 | 1.1711 | 0.4101 | 0.112* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0716 (5) | 0.0430 (4) | 0.0419 (4) | −0.0002 (3) | −0.0117 (3) | −0.0140 (3) |
S1 | 0.0234 (5) | 0.0507 (7) | 0.0420 (7) | −0.0043 (5) | −0.0094 (5) | 0.0013 (6) |
O1 | 0.0333 (16) | 0.0353 (17) | 0.0331 (18) | −0.0088 (13) | −0.0132 (13) | −0.0042 (14) |
O2 | 0.0391 (19) | 0.068 (3) | 0.070 (3) | −0.0237 (18) | −0.0217 (19) | 0.015 (2) |
C1 | 0.026 (2) | 0.031 (2) | 0.037 (3) | −0.0052 (17) | −0.0097 (18) | 0.0021 (19) |
C2 | 0.026 (2) | 0.028 (2) | 0.033 (2) | −0.0085 (16) | −0.0128 (17) | 0.0018 (18) |
C3 | 0.042 (3) | 0.029 (2) | 0.036 (3) | −0.0090 (19) | −0.015 (2) | 0.001 (2) |
C4 | 0.046 (3) | 0.028 (2) | 0.028 (2) | −0.0071 (19) | −0.0085 (19) | −0.0049 (18) |
C5 | 0.033 (2) | 0.034 (2) | 0.036 (3) | −0.0050 (19) | −0.0055 (19) | 0.003 (2) |
C6 | 0.024 (2) | 0.039 (3) | 0.044 (3) | −0.0084 (18) | −0.014 (2) | 0.005 (2) |
C7 | 0.031 (2) | 0.031 (2) | 0.026 (2) | −0.0122 (17) | −0.0111 (17) | −0.0006 (17) |
C8 | 0.034 (2) | 0.031 (2) | 0.027 (2) | −0.0066 (18) | −0.0106 (18) | 0.0022 (18) |
C9 | 0.051 (3) | 0.053 (3) | 0.059 (4) | −0.006 (2) | −0.032 (3) | −0.018 (3) |
C10 | 0.035 (3) | 0.059 (3) | 0.048 (3) | 0.002 (2) | −0.001 (2) | −0.002 (3) |
C11 | 0.046 (3) | 0.044 (3) | 0.037 (3) | −0.005 (2) | −0.003 (2) | −0.009 (2) |
C12 | 0.027 (2) | 0.034 (2) | 0.041 (3) | 0.0061 (18) | −0.0106 (19) | −0.005 (2) |
C13 | 0.039 (3) | 0.037 (3) | 0.050 (3) | −0.004 (2) | −0.018 (2) | −0.006 (2) |
C14 | 0.057 (3) | 0.041 (3) | 0.037 (3) | 0.006 (2) | −0.020 (2) | −0.010 (2) |
C15 | 0.056 (3) | 0.032 (3) | 0.038 (3) | 0.006 (2) | −0.007 (2) | −0.010 (2) |
C16 | 0.053 (3) | 0.034 (3) | 0.054 (4) | −0.009 (2) | −0.010 (3) | −0.001 (2) |
C17 | 0.044 (3) | 0.040 (3) | 0.043 (3) | −0.008 (2) | −0.017 (2) | −0.006 (2) |
C18 | 0.111 (6) | 0.051 (4) | 0.040 (4) | 0.001 (4) | −0.006 (4) | 0.002 (3) |
Br1—C4 | 1.918 (5) | C10—H10A | 0.9800 |
S1—O2 | 1.485 (4) | C10—H10B | 0.9800 |
S1—C1 | 1.772 (5) | C10—H10C | 0.9800 |
S1—C12 | 1.785 (5) | C11—H11A | 0.9800 |
O1—C8 | 1.374 (6) | C11—H11B | 0.9800 |
O1—C7 | 1.375 (6) | C11—H11C | 0.9800 |
C1—C8 | 1.337 (7) | C12—C13 | 1.378 (8) |
C1—C2 | 1.456 (6) | C12—C17 | 1.384 (7) |
C2—C7 | 1.392 (6) | C13—C14 | 1.389 (8) |
C2—C3 | 1.405 (7) | C13—H13 | 0.9500 |
C3—C4 | 1.393 (7) | C14—C15 | 1.378 (8) |
C3—C9 | 1.497 (7) | C14—H14 | 0.9500 |
C4—C5 | 1.406 (7) | C15—C16 | 1.391 (9) |
C5—C6 | 1.384 (7) | C15—C18 | 1.497 (8) |
C5—C10 | 1.515 (7) | C16—C17 | 1.375 (8) |
C6—C7 | 1.378 (6) | C16—H16 | 0.9500 |
C6—H6 | 0.9500 | C17—H17 | 0.9500 |
C8—C11 | 1.490 (7) | C18—H18A | 0.9800 |
C9—H9A | 0.9800 | C18—H18B | 0.9800 |
C9—H9B | 0.9800 | C18—H18C | 0.9800 |
C9—H9C | 0.9800 | ||
O2—S1—C1 | 110.8 (2) | C5—C10—H10B | 109.5 |
O2—S1—C12 | 106.7 (2) | H10A—C10—H10B | 109.5 |
C1—S1—C12 | 99.4 (2) | C5—C10—H10C | 109.5 |
C8—O1—C7 | 106.3 (3) | H10A—C10—H10C | 109.5 |
C8—C1—C2 | 107.6 (4) | H10B—C10—H10C | 109.5 |
C8—C1—S1 | 117.8 (4) | C8—C11—H11A | 109.5 |
C2—C1—S1 | 134.5 (4) | C8—C11—H11B | 109.5 |
C7—C2—C3 | 119.4 (4) | H11A—C11—H11B | 109.5 |
C7—C2—C1 | 104.1 (4) | C8—C11—H11C | 109.5 |
C3—C2—C1 | 136.6 (4) | H11A—C11—H11C | 109.5 |
C4—C3—C2 | 114.9 (4) | H11B—C11—H11C | 109.5 |
C4—C3—C9 | 122.9 (5) | C13—C12—C17 | 120.2 (5) |
C2—C3—C9 | 122.2 (4) | C13—C12—S1 | 120.4 (4) |
C3—C4—C5 | 125.7 (4) | C17—C12—S1 | 118.8 (4) |
C3—C4—Br1 | 116.9 (4) | C12—C13—C14 | 119.5 (5) |
C5—C4—Br1 | 117.4 (4) | C12—C13—H13 | 120.2 |
C6—C5—C4 | 118.0 (4) | C14—C13—H13 | 120.2 |
C6—C5—C10 | 119.3 (5) | C15—C14—C13 | 120.9 (5) |
C4—C5—C10 | 122.7 (5) | C15—C14—H14 | 119.6 |
C7—C6—C5 | 117.2 (4) | C13—C14—H14 | 119.6 |
C7—C6—H6 | 121.4 | C14—C15—C16 | 118.8 (5) |
C5—C6—H6 | 121.4 | C14—C15—C18 | 121.9 (6) |
O1—C7—C6 | 124.4 (4) | C16—C15—C18 | 119.3 (6) |
O1—C7—C2 | 110.8 (4) | C17—C16—C15 | 120.8 (5) |
C6—C7—C2 | 124.8 (4) | C17—C16—H16 | 119.6 |
C1—C8—O1 | 111.2 (4) | C15—C16—H16 | 119.6 |
C1—C8—C11 | 134.7 (5) | C16—C17—C12 | 119.8 (5) |
O1—C8—C11 | 114.0 (4) | C16—C17—H17 | 120.1 |
C3—C9—H9A | 109.5 | C12—C17—H17 | 120.1 |
C3—C9—H9B | 109.5 | C15—C18—H18A | 109.5 |
H9A—C9—H9B | 109.5 | C15—C18—H18B | 109.5 |
C3—C9—H9C | 109.5 | H18A—C18—H18B | 109.5 |
H9A—C9—H9C | 109.5 | C15—C18—H18C | 109.5 |
H9B—C9—H9C | 109.5 | H18A—C18—H18C | 109.5 |
C5—C10—H10A | 109.5 | H18B—C18—H18C | 109.5 |
O2—S1—C1—C8 | −134.4 (4) | C5—C6—C7—C2 | 0.5 (7) |
C12—S1—C1—C8 | 113.6 (4) | C3—C2—C7—O1 | −179.3 (4) |
O2—S1—C1—C2 | 48.7 (5) | C1—C2—C7—O1 | 1.0 (5) |
C12—S1—C1—C2 | −63.3 (5) | C3—C2—C7—C6 | 1.7 (7) |
C8—C1—C2—C7 | −0.9 (5) | C1—C2—C7—C6 | −178.0 (4) |
S1—C1—C2—C7 | 176.2 (4) | C2—C1—C8—O1 | 0.6 (5) |
C8—C1—C2—C3 | 179.5 (5) | S1—C1—C8—O1 | −177.1 (3) |
S1—C1—C2—C3 | −3.4 (8) | C2—C1—C8—C11 | 178.4 (5) |
C7—C2—C3—C4 | −2.6 (6) | S1—C1—C8—C11 | 0.7 (7) |
C1—C2—C3—C4 | 177.0 (5) | C7—O1—C8—C1 | 0.0 (5) |
C7—C2—C3—C9 | 176.4 (5) | C7—O1—C8—C11 | −178.3 (4) |
C1—C2—C3—C9 | −4.1 (8) | O2—S1—C12—C13 | 10.6 (4) |
C2—C3—C4—C5 | 1.6 (7) | C1—S1—C12—C13 | 125.8 (4) |
C9—C3—C4—C5 | −177.3 (5) | O2—S1—C12—C17 | −177.8 (4) |
C2—C3—C4—Br1 | −176.7 (3) | C1—S1—C12—C17 | −62.6 (4) |
C9—C3—C4—Br1 | 4.4 (6) | C17—C12—C13—C14 | 1.6 (7) |
C3—C4—C5—C6 | 0.5 (7) | S1—C12—C13—C14 | 173.0 (4) |
Br1—C4—C5—C6 | 178.8 (3) | C12—C13—C14—C15 | −0.6 (8) |
C3—C4—C5—C10 | 179.4 (5) | C13—C14—C15—C16 | 0.4 (8) |
Br1—C4—C5—C10 | −2.3 (6) | C13—C14—C15—C18 | −179.2 (5) |
C4—C5—C6—C7 | −1.5 (6) | C14—C15—C16—C17 | −1.3 (8) |
C10—C5—C6—C7 | 179.5 (4) | C18—C15—C16—C17 | 178.4 (5) |
C8—O1—C7—C6 | 178.3 (4) | C15—C16—C17—C12 | 2.2 (8) |
C8—O1—C7—C2 | −0.7 (4) | C13—C12—C17—C16 | −2.4 (7) |
C5—C6—C7—O1 | −178.3 (4) | S1—C12—C17—C16 | −174.0 (4) |
Cg2 is the centroid of the C1/C2/C7/O1/C8 furan ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O2i | 0.95 | 2.32 | 3.181 (6) | 151 |
C17—H17···O1ii | 0.95 | 2.58 | 3.456 (6) | 154 |
C11—H11A···Cg2ii | 0.98 | 2.83 | 3.794 (6) | 167 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+2, −z+2. |
Cg2 is the centroid of the C1/C2/C7/O1/C8 furan ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O2i | 0.95 | 2.32 | 3.181 (6) | 150.6 |
C17—H17···O1ii | 0.95 | 2.58 | 3.456 (6) | 154.2 |
C11—H11A···Cg2ii | 0.98 | 2.83 | 3.794 (6) | 167.4 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+2, −z+2. |
References
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As a part of our continuing study of 5-bromo-2,4,6-trimethyl-1-benzofuran derivatives containing phenylsulfinyl (Choi et al., 2008) and 4-fluorophenylsulfinyl (Choi et al., 2011) substituents in 3-position, we report here the crystal structure of the title compound.
In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.017 (3) Å from the least-squares plane defined by the nine constituent atoms. The 4-methylphenyl ring is essentially planar, with a mean deviation of 0.007 (4) Å from the least-squares plane defined by the six constituent atoms. The dihedral angle formed by the benzofuran ring system and the 4-methylphenyl ring is 87.0 (2)°. In the crystal structure, Fig. 2, the molecules related by inversion are paired into dimers via C—H···O and C—H···π interactions (Table 1, Cg2 is the centroid of the C1/C2/C7/O1/C8 furan ring). These dimers are further packed by intermolecular C—H···O hydrogen bonds (Table 1) and π···π interactions between the benzene and furan rings of neighbouring molecules, with a Cg1···Cg2iii distance of 3.555 (5) Å and an interplanar distance of 3.499 (5) Å resulting in a slippage of 0.629 (5) Å (Cg1 is the centroid of the C2–C7 benzene ring), resulting in a three-dimensional network.