organic compounds
Diphenylmethyl benzoate
aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and cR. L. Fine Chem, Bengaluru, 560 064, India
*Correspondence e-mail: jjasinski@keene.edu
In the title molecule, C20H16O2, the dihedral angle between the phenyl rings of the diphenylmethyl group is 68.3 (2)°. The benzoate group is essentially planar, with a maximum deviation of 0.017 (2) Å for the carbonyl O atom, and the two phenyl rings are twisted by 27.5 (4) and 85.6 (9)° from this plane. In the crystal, weak C—H⋯O hydrogen bonds link molecules along [100].
Related literature
For related structures, see: Baidya et al. (2009a,b); Gowda et al. (2007, 2009). For standard bond lengths, see: Allen et al. (1987).
Experimental
Crystal data
|
Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
https://doi.org/10.1107/S1600536812050064/lh5566sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812050064/lh5566Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812050064/lh5566Isup3.cml
The title compound was obtained as a gift sample from R. L. Fine Chem, Bengaluru, India. X-ray quality crystals were obtained by slow evaporation of acetone and acetone solution (m.p.: 353–355 K).
All of the H atoms were placed in their calculated positions and then refined using the riding model with Atom—H lengths of 0.93Å (CH). Isotropic displacement parameters for these atoms were set to 1.19-1.20 (CH) times Ueq of the parent atom.
Benzyl Benzoate is widely used in the perfume and pharmaceutical industries. The crystal structures of some related compounds, viz., 4,4'-bis(dimethylamino)benzhydryl phenyl sulfone (Baidya et al., 2009a), benzhydryl phenyl sulfone (Baidya et al., 2009b), 4-methylphenyl benzoate (Gowda et al., 2007), 2,4-dimethylphenyl 4-methylbenzoate (Gowda et al., 2009) have been reported. In view of the importance of benzoates, the paper reports the
of the title compound, (I).The molecular structure of the title compound is shown in Fig. 1. The dihedral angle between the two phenyl rings (C9-C14 and C15-C20) is 68.3 (2)°. The mean plane of the benzoate group (C1–C7/O1/O2, with a maximum deviation of 0.017 (2)Å for O2) is twisted by 27.5 (4)° (C9–C14) and 85.6 (9)° (C15–C20), respectively, from that of the phenyl rings. In the crystal, weak C—H···O hydrogen bonds (Table 1) link molecules along [100] (Fig. 2).
For related structures, see: Baidya et al. (2009a,b); Gowda et al. (2007, 2009). For standard bond lengths, see: Allen et al. (1987).
Data collection: CrysAlis PRO (Agilent, 2012); cell
CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C20H16O2 | F(000) = 304 |
Mr = 288.33 | Dx = 1.254 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: P 2yb | Cell parameters from 2446 reflections |
a = 5.75357 (19) Å | θ = 5.3–72.4° |
b = 16.0368 (5) Å | µ = 0.63 mm−1 |
c = 8.3114 (3) Å | T = 173 K |
β = 95.340 (3)° | Block, colorless |
V = 763.55 (4) Å3 | 0.38 × 0.26 × 0.24 mm |
Z = 2 |
Agilent Xcalibur (Eos, Gemini) diffractometer | 2659 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 2528 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
Detector resolution: 16.0416 pixels mm-1 | θmax = 72.5°, θmin = 5.4° |
ω scans | h = −7→5 |
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012) | k = −17→19 |
Tmin = 0.912, Tmax = 1.000 | l = −6→10 |
4414 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.035 | w = 1/[σ2(Fo2) + (0.0518P)2 + 0.052P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.094 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.21 e Å−3 |
2659 reflections | Δρmin = −0.15 e Å−3 |
200 parameters | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.0104 (11) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983) 1120 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.0 (2) |
C20H16O2 | V = 763.55 (4) Å3 |
Mr = 288.33 | Z = 2 |
Monoclinic, P21 | Cu Kα radiation |
a = 5.75357 (19) Å | µ = 0.63 mm−1 |
b = 16.0368 (5) Å | T = 173 K |
c = 8.3114 (3) Å | 0.38 × 0.26 × 0.24 mm |
β = 95.340 (3)° |
Agilent Xcalibur (Eos, Gemini) diffractometer | 2659 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012) | 2528 reflections with I > 2σ(I) |
Tmin = 0.912, Tmax = 1.000 | Rint = 0.022 |
4414 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.094 | Δρmax = 0.21 e Å−3 |
S = 1.06 | Δρmin = −0.15 e Å−3 |
2659 reflections | Absolute structure: Flack (1983) 1120 Friedel pairs |
200 parameters | Absolute structure parameter: 0.0 (2) |
1 restraint |
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 > σ(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 | ||
O1 | 0.2173 (2) | 0.33454 (8) | 0.50213 (15) | 0.0376 (3) | |
O2 | −0.1042 (2) | 0.31628 (10) | 0.63104 (18) | 0.0495 (4) | |
C1 | 0.1598 (3) | 0.42599 (10) | 0.7144 (2) | 0.0312 (4) | |
C2 | 0.3646 (3) | 0.46769 (11) | 0.6891 (2) | 0.0364 (4) | |
H2 | 0.4547 | 0.4498 | 0.6085 | 0.044* | |
C3 | 0.4349 (4) | 0.53567 (12) | 0.7833 (2) | 0.0434 (4) | |
H3 | 0.5709 | 0.5640 | 0.7648 | 0.052* | |
C4 | 0.3036 (4) | 0.56172 (13) | 0.9049 (2) | 0.0465 (5) | |
H4 | 0.3514 | 0.6074 | 0.9685 | 0.056* | |
C5 | 0.1008 (4) | 0.51969 (13) | 0.9320 (2) | 0.0491 (5) | |
H5 | 0.0133 | 0.5370 | 1.0145 | 0.059* | |
C6 | 0.0279 (3) | 0.45254 (12) | 0.8375 (2) | 0.0407 (4) | |
H6 | −0.1092 | 0.4248 | 0.8556 | 0.049* | |
C7 | 0.0735 (3) | 0.35370 (11) | 0.6150 (2) | 0.0329 (4) | |
C8 | 0.1615 (3) | 0.26034 (11) | 0.4044 (2) | 0.0339 (4) | |
H8 | −0.0074 | 0.2579 | 0.3758 | 0.041* | |
C9 | 0.2833 (3) | 0.27104 (10) | 0.2523 (2) | 0.0350 (4) | |
C10 | 0.4936 (3) | 0.31388 (13) | 0.2513 (2) | 0.0408 (4) | |
H10 | 0.5615 | 0.3381 | 0.3459 | 0.049* | |
C11 | 0.6021 (4) | 0.32051 (14) | 0.1099 (3) | 0.0459 (5) | |
H11 | 0.7420 | 0.3495 | 0.1101 | 0.055* | |
C12 | 0.5040 (4) | 0.28435 (12) | −0.0315 (2) | 0.0452 (5) | |
H12 | 0.5776 | 0.2890 | −0.1261 | 0.054* | |
C13 | 0.2964 (4) | 0.24132 (14) | −0.0317 (2) | 0.0459 (5) | |
H13 | 0.2304 | 0.2166 | −0.1264 | 0.055* | |
C14 | 0.1859 (3) | 0.23482 (12) | 0.1092 (2) | 0.0400 (4) | |
H14 | 0.0455 | 0.2060 | 0.1081 | 0.048* | |
C15 | 0.2380 (3) | 0.18357 (11) | 0.50053 (19) | 0.0327 (4) | |
C16 | 0.4629 (3) | 0.17795 (12) | 0.5773 (2) | 0.0381 (4) | |
H16 | 0.5683 | 0.2212 | 0.5672 | 0.046* | |
C17 | 0.5304 (4) | 0.10861 (14) | 0.6684 (2) | 0.0456 (5) | |
H17 | 0.6804 | 0.1056 | 0.7204 | 0.055* | |
C18 | 0.3756 (4) | 0.04356 (13) | 0.6827 (2) | 0.0494 (5) | |
H18 | 0.4206 | −0.0028 | 0.7452 | 0.059* | |
C19 | 0.1538 (4) | 0.04782 (13) | 0.6037 (3) | 0.0514 (5) | |
H19 | 0.0504 | 0.0038 | 0.6115 | 0.062* | |
C20 | 0.0851 (4) | 0.11732 (13) | 0.5130 (2) | 0.0421 (4) | |
H20 | −0.0644 | 0.1197 | 0.4601 | 0.051* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0385 (7) | 0.0341 (7) | 0.0422 (7) | −0.0057 (5) | 0.0136 (5) | −0.0087 (5) |
O2 | 0.0401 (7) | 0.0565 (9) | 0.0543 (8) | −0.0152 (6) | 0.0172 (6) | −0.0205 (7) |
C1 | 0.0333 (8) | 0.0287 (8) | 0.0316 (8) | 0.0040 (6) | 0.0032 (6) | 0.0031 (6) |
C2 | 0.0354 (9) | 0.0348 (9) | 0.0396 (9) | −0.0008 (7) | 0.0058 (7) | 0.0002 (7) |
C3 | 0.0415 (10) | 0.0386 (10) | 0.0494 (11) | −0.0062 (8) | 0.0002 (8) | 0.0021 (9) |
C4 | 0.0569 (12) | 0.0358 (10) | 0.0451 (10) | −0.0034 (9) | −0.0047 (9) | −0.0076 (8) |
C5 | 0.0602 (13) | 0.0475 (12) | 0.0410 (11) | 0.0031 (10) | 0.0129 (9) | −0.0103 (9) |
C6 | 0.0410 (10) | 0.0402 (10) | 0.0419 (10) | −0.0016 (8) | 0.0082 (8) | −0.0030 (8) |
C7 | 0.0318 (8) | 0.0333 (9) | 0.0340 (8) | 0.0016 (7) | 0.0047 (7) | −0.0001 (7) |
C8 | 0.0327 (8) | 0.0345 (9) | 0.0349 (8) | −0.0039 (7) | 0.0050 (7) | −0.0062 (7) |
C9 | 0.0395 (9) | 0.0303 (9) | 0.0354 (8) | 0.0045 (7) | 0.0056 (7) | 0.0010 (7) |
C10 | 0.0428 (10) | 0.0413 (10) | 0.0393 (9) | −0.0018 (8) | 0.0088 (8) | −0.0016 (8) |
C11 | 0.0495 (11) | 0.0415 (11) | 0.0487 (10) | 0.0004 (9) | 0.0152 (8) | 0.0058 (9) |
C12 | 0.0589 (12) | 0.0427 (11) | 0.0363 (9) | 0.0099 (9) | 0.0172 (9) | 0.0070 (8) |
C13 | 0.0609 (12) | 0.0443 (11) | 0.0324 (9) | 0.0086 (9) | 0.0032 (8) | −0.0021 (8) |
C14 | 0.0420 (9) | 0.0379 (10) | 0.0401 (9) | 0.0039 (8) | 0.0035 (8) | −0.0035 (8) |
C15 | 0.0374 (9) | 0.0340 (9) | 0.0282 (8) | −0.0040 (7) | 0.0108 (7) | −0.0075 (6) |
C16 | 0.0391 (10) | 0.0423 (10) | 0.0338 (9) | −0.0060 (8) | 0.0076 (7) | −0.0023 (7) |
C17 | 0.0448 (11) | 0.0580 (13) | 0.0349 (9) | 0.0062 (9) | 0.0083 (8) | 0.0008 (9) |
C18 | 0.0722 (15) | 0.0392 (11) | 0.0382 (10) | 0.0059 (10) | 0.0123 (9) | 0.0006 (8) |
C19 | 0.0683 (14) | 0.0364 (11) | 0.0504 (11) | −0.0152 (10) | 0.0108 (10) | −0.0032 (9) |
C20 | 0.0421 (10) | 0.0423 (10) | 0.0427 (10) | −0.0100 (8) | 0.0073 (8) | −0.0065 (8) |
O1—C7 | 1.343 (2) | C10—C11 | 1.385 (3) |
O1—C8 | 1.460 (2) | C10—H10 | 0.9300 |
O2—C7 | 1.203 (2) | C11—C12 | 1.383 (3) |
C1—C2 | 1.388 (2) | C11—H11 | 0.9300 |
C1—C6 | 1.396 (2) | C12—C13 | 1.379 (3) |
C1—C7 | 1.482 (2) | C12—H12 | 0.9300 |
C2—C3 | 1.381 (3) | C13—C14 | 1.387 (3) |
C2—H2 | 0.9300 | C13—H13 | 0.9300 |
C3—C4 | 1.382 (3) | C14—H14 | 0.9300 |
C3—H3 | 0.9300 | C15—C20 | 1.390 (2) |
C4—C5 | 1.384 (3) | C15—C16 | 1.392 (2) |
C4—H4 | 0.9300 | C16—C17 | 1.380 (3) |
C5—C6 | 1.375 (3) | C16—H16 | 0.9300 |
C5—H5 | 0.9300 | C17—C18 | 1.384 (3) |
C6—H6 | 0.9300 | C17—H17 | 0.9300 |
C8—C15 | 1.511 (3) | C18—C19 | 1.381 (3) |
C8—C9 | 1.511 (2) | C18—H18 | 0.9300 |
C8—H8 | 0.9800 | C19—C20 | 1.382 (3) |
C9—C10 | 1.392 (3) | C19—H19 | 0.9300 |
C9—C14 | 1.394 (3) | C20—H20 | 0.9300 |
C7—O1—C8 | 117.21 (13) | C11—C10—H10 | 119.9 |
C2—C1—C6 | 119.42 (17) | C9—C10—H10 | 119.9 |
C2—C1—C7 | 122.53 (15) | C12—C11—C10 | 120.54 (19) |
C6—C1—C7 | 118.05 (16) | C12—C11—H11 | 119.7 |
C3—C2—C1 | 120.18 (18) | C10—C11—H11 | 119.7 |
C3—C2—H2 | 119.9 | C13—C12—C11 | 119.72 (17) |
C1—C2—H2 | 119.9 | C13—C12—H12 | 120.1 |
C2—C3—C4 | 120.15 (18) | C11—C12—H12 | 120.1 |
C2—C3—H3 | 119.9 | C12—C13—C14 | 120.08 (18) |
C4—C3—H3 | 119.9 | C12—C13—H13 | 120.0 |
C3—C4—C5 | 119.89 (18) | C14—C13—H13 | 120.0 |
C3—C4—H4 | 120.1 | C13—C14—C9 | 120.65 (18) |
C5—C4—H4 | 120.1 | C13—C14—H14 | 119.7 |
C6—C5—C4 | 120.37 (19) | C9—C14—H14 | 119.7 |
C6—C5—H5 | 119.8 | C20—C15—C16 | 118.97 (17) |
C4—C5—H5 | 119.8 | C20—C15—C8 | 120.50 (16) |
C5—C6—C1 | 119.98 (18) | C16—C15—C8 | 120.53 (16) |
C5—C6—H6 | 120.0 | C17—C16—C15 | 120.40 (18) |
C1—C6—H6 | 120.0 | C17—C16—H16 | 119.8 |
O2—C7—O1 | 123.26 (16) | C15—C16—H16 | 119.8 |
O2—C7—C1 | 124.91 (16) | C16—C17—C18 | 120.2 (2) |
O1—C7—C1 | 111.83 (14) | C16—C17—H17 | 119.9 |
O1—C8—C15 | 109.39 (13) | C18—C17—H17 | 119.9 |
O1—C8—C9 | 106.13 (14) | C19—C18—C17 | 119.7 (2) |
C15—C8—C9 | 113.59 (14) | C19—C18—H18 | 120.1 |
O1—C8—H8 | 109.2 | C17—C18—H18 | 120.1 |
C15—C8—H8 | 109.2 | C18—C19—C20 | 120.2 (2) |
C9—C8—H8 | 109.2 | C18—C19—H19 | 119.9 |
C10—C9—C14 | 118.75 (16) | C20—C19—H19 | 119.9 |
C10—C9—C8 | 122.17 (15) | C19—C20—C15 | 120.42 (19) |
C14—C9—C8 | 119.06 (16) | C19—C20—H20 | 119.8 |
C11—C10—C9 | 120.26 (18) | C15—C20—H20 | 119.8 |
C6—C1—C2—C3 | −1.1 (3) | C14—C9—C10—C11 | 0.4 (3) |
C7—C1—C2—C3 | 178.80 (17) | C8—C9—C10—C11 | 178.47 (18) |
C1—C2—C3—C4 | 1.0 (3) | C9—C10—C11—C12 | −0.4 (3) |
C2—C3—C4—C5 | −0.2 (3) | C10—C11—C12—C13 | 0.0 (3) |
C3—C4—C5—C6 | −0.6 (3) | C11—C12—C13—C14 | 0.4 (3) |
C4—C5—C6—C1 | 0.5 (3) | C12—C13—C14—C9 | −0.4 (3) |
C2—C1—C6—C5 | 0.3 (3) | C10—C9—C14—C13 | 0.0 (3) |
C7—C1—C6—C5 | −179.60 (17) | C8—C9—C14—C13 | −178.14 (17) |
C8—O1—C7—O2 | −5.1 (3) | O1—C8—C15—C20 | 129.89 (16) |
C8—O1—C7—C1 | 175.31 (13) | C9—C8—C15—C20 | −111.75 (18) |
C2—C1—C7—O2 | −179.04 (19) | O1—C8—C15—C16 | −50.40 (19) |
C6—C1—C7—O2 | 0.8 (3) | C9—C8—C15—C16 | 68.0 (2) |
C2—C1—C7—O1 | 0.5 (2) | C20—C15—C16—C17 | −1.9 (3) |
C6—C1—C7—O1 | −179.61 (16) | C8—C15—C16—C17 | 178.38 (15) |
C7—O1—C8—C15 | −78.53 (17) | C15—C16—C17—C18 | 0.7 (3) |
C7—O1—C8—C9 | 158.56 (14) | C16—C17—C18—C19 | 0.8 (3) |
O1—C8—C9—C10 | 31.5 (2) | C17—C18—C19—C20 | −1.1 (3) |
C15—C8—C9—C10 | −88.7 (2) | C18—C19—C20—C15 | −0.1 (3) |
O1—C8—C9—C14 | −150.37 (15) | C16—C15—C20—C19 | 1.6 (3) |
C15—C8—C9—C14 | 89.40 (19) | C8—C15—C20—C19 | −178.71 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16···O2i | 0.93 | 2.44 | 3.334 (2) | 160 |
Symmetry code: (i) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C20H16O2 |
Mr | 288.33 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 173 |
a, b, c (Å) | 5.75357 (19), 16.0368 (5), 8.3114 (3) |
β (°) | 95.340 (3) |
V (Å3) | 763.55 (4) |
Z | 2 |
Radiation type | Cu Kα |
µ (mm−1) | 0.63 |
Crystal size (mm) | 0.38 × 0.26 × 0.24 |
Data collection | |
Diffractometer | Agilent Xcalibur (Eos, Gemini) |
Absorption correction | Multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012) |
Tmin, Tmax | 0.912, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4414, 2659, 2528 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.619 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.094, 1.06 |
No. of reflections | 2659 |
No. of parameters | 200 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.15 |
Absolute structure | Flack (1983) 1120 Friedel pairs |
Absolute structure parameter | 0.0 (2) |
Computer programs: CrysAlis PRO (Agilent, 2012), CrysAlis RED (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16···O2i | 0.93 | 2.44 | 3.334 (2) | 160 |
Symmetry code: (i) x+1, y, z. |
Acknowledgements
MK thanks the UOM for research facilities. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.
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Benzyl Benzoate is widely used in the perfume and pharmaceutical industries. The crystal structures of some related compounds, viz., 4,4'-bis(dimethylamino)benzhydryl phenyl sulfone (Baidya et al., 2009a), benzhydryl phenyl sulfone (Baidya et al., 2009b), 4-methylphenyl benzoate (Gowda et al., 2007), 2,4-dimethylphenyl 4-methylbenzoate (Gowda et al., 2009) have been reported. In view of the importance of benzoates, the paper reports the crystal structure of the title compound, (I).
The molecular structure of the title compound is shown in Fig. 1. The dihedral angle between the two phenyl rings (C9-C14 and C15-C20) is 68.3 (2)°. The mean plane of the benzoate group (C1–C7/O1/O2, with a maximum deviation of 0.017 (2)Å for O2) is twisted by 27.5 (4)° (C9–C14) and 85.6 (9)° (C15–C20), respectively, from that of the phenyl rings. In the crystal, weak C—H···O hydrogen bonds (Table 1) link molecules along [100] (Fig. 2).