organic compounds
N-Benzyl-2-hydroxybenzamide
aCollege of Materials Science and Chemical Engineering, Jinhua College of Profession and Technology, Jinhua, Zhejiang 321017, People's Republic of China
*Correspondence e-mail: zbs_jy@163.com
In the title compound, C14H13NO2, the mean planes through the benzyl and 2-hydoxybenzamide units make a dihedral angle of 68.81 (7)°. There is an intramolecular O—H⋯O hydrogen bond involving the carbonyl O atom and the 2-hydroxy substituent. In the N—H⋯O hydrogen bonds link symmetry-related molecules into one-dimensional chains extending along the a-axis direction. These chains are further connected via C—H⋯O hydrogen bonds, forming a sheet-like structure
Experimental
Crystal data
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Refinement
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Data collection: RAPID-AUTO (Rigaku, 1998); cell RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); 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: SHELXL97.
Supporting information
10.1107/S1600536808010453/su2048sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808010453/su2048Isup2.hkl
Freshly prepared CuCO3 (0.310 g 2.50 mmol), [C6H4(COOC6H4CONHCH2ph)2](0.350 g 0.601 mmol), 2-chloro-benzoic acid (0.160 g 1.022 mmol), and 15 ml CH3OH/H2O (1:2,v/v) were mixed and stirred for ca. 1.5 h. The resulting suspension was heated in a 23 ml Teflon-lined stainless steel autoclave at 373 K for 7 days. After the autoclave was cooled to room temperature, and colorless block-like crystals, suitable for X-ray analysis, were obtained.
All of the H atoms were located in difference Fourier syntheses and were freely refined: O-H = 0.98 (3), N-H = 0.882 (18), and C-H = 0.94 (2) - 1.010 (16) Å.
Data collection: RAPID-AUTO (Rigaku, 1998); cell
RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); 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: SHELXL97 (Sheldrick, 2008).C14H13NO2 | F(000) = 480 |
Mr = 227.25 | Dx = 1.296 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 6913 reflections |
a = 12.478 (3) Å | θ = 3.0–27.5° |
b = 8.3503 (17) Å | µ = 0.09 mm−1 |
c = 12.664 (3) Å | T = 290 K |
β = 118.02 (3)° | Block, colorless |
V = 1164.9 (6) Å3 | 0.33 × 0.22 × 0.20 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 2665 independent reflections |
Radiation source: fine-focus sealed tube | 1648 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
Detector resolution: 10 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
ω scans | h = −15→16 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −10→10 |
Tmin = 0.977, Tmax = 0.983 | l = −16→16 |
11112 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | All H-atom parameters refined |
wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.0564P)2 + 0.0491P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
2665 reflections | Δρmax = 0.17 e Å−3 |
207 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.011 (2) |
C14H13NO2 | V = 1164.9 (6) Å3 |
Mr = 227.25 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.478 (3) Å | µ = 0.09 mm−1 |
b = 8.3503 (17) Å | T = 290 K |
c = 12.664 (3) Å | 0.33 × 0.22 × 0.20 mm |
β = 118.02 (3)° |
Rigaku R-AXIS RAPID diffractometer | 2665 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 1648 reflections with I > 2σ(I) |
Tmin = 0.977, Tmax = 0.983 | Rint = 0.037 |
11112 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.116 | All H-atom parameters refined |
S = 1.03 | Δρmax = 0.17 e Å−3 |
2665 reflections | Δρmin = −0.14 e Å−3 |
207 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles |
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 | 0.29704 (10) | 0.74227 (17) | −0.23736 (9) | 0.0731 (4) | |
O2 | 0.49480 (9) | 0.60089 (14) | −0.16419 (9) | 0.0600 (4) | |
N1 | 0.64585 (9) | 0.63326 (15) | 0.02206 (11) | 0.0449 (4) | |
C1 | 0.45255 (11) | 0.76116 (16) | −0.03318 (11) | 0.0396 (4) | |
C2 | 0.48553 (14) | 0.82179 (19) | 0.07995 (14) | 0.0493 (5) | |
C3 | 0.40715 (15) | 0.9140 (2) | 0.10230 (16) | 0.0592 (6) | |
C4 | 0.29300 (15) | 0.9477 (2) | 0.01061 (17) | 0.0604 (6) | |
C5 | 0.25762 (14) | 0.8909 (2) | −0.10172 (16) | 0.0576 (6) | |
C6 | 0.33637 (12) | 0.79771 (18) | −0.12499 (13) | 0.0478 (5) | |
C7 | 0.53270 (11) | 0.66022 (17) | −0.06264 (12) | 0.0412 (4) | |
C8 | 0.73259 (14) | 0.5375 (2) | 0.00128 (16) | 0.0508 (5) | |
C9 | 0.80422 (12) | 0.63678 (17) | −0.04347 (14) | 0.0460 (5) | |
C10 | 0.92320 (15) | 0.6768 (3) | 0.03099 (19) | 0.0722 (7) | |
C11 | 0.98716 (18) | 0.7699 (3) | −0.0108 (2) | 0.0875 (9) | |
C12 | 0.9333 (2) | 0.8228 (3) | −0.1254 (2) | 0.0785 (9) | |
C13 | 0.81540 (19) | 0.7850 (3) | −0.20000 (19) | 0.0721 (8) | |
C14 | 0.75139 (16) | 0.6917 (2) | −0.15893 (16) | 0.0596 (6) | |
HN1 | 0.6728 (14) | 0.6819 (19) | 0.0917 (16) | 0.059 (5)* | |
H2 | 0.5651 (15) | 0.7995 (18) | 0.1431 (15) | 0.060 (5)* | |
HO1 | 0.367 (2) | 0.681 (3) | −0.230 (2) | 0.106 (7)* | |
H3 | 0.4331 (15) | 0.952 (2) | 0.1817 (17) | 0.078 (5)* | |
H4 | 0.2386 (15) | 1.009 (2) | 0.0252 (15) | 0.071 (5)* | |
H5 | 0.1770 (17) | 0.913 (2) | −0.1697 (16) | 0.081 (5)* | |
H8A | 0.6833 (14) | 0.455 (2) | −0.0610 (14) | 0.062 (5)* | |
H8B | 0.7896 (14) | 0.4913 (19) | 0.0805 (15) | 0.062 (5)* | |
H10 | 0.9607 (17) | 0.633 (2) | 0.1088 (19) | 0.087 (6)* | |
H11 | 1.070 (2) | 0.793 (3) | 0.042 (2) | 0.107 (7)* | |
H12 | 0.9743 (19) | 0.887 (3) | −0.1597 (18) | 0.099 (7)* | |
H13 | 0.7716 (18) | 0.825 (3) | −0.283 (2) | 0.098 (7)* | |
H14 | 0.6696 (16) | 0.668 (2) | −0.2122 (15) | 0.070 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0512 (6) | 0.1059 (10) | 0.0395 (6) | 0.0150 (7) | 0.0024 (5) | −0.0056 (6) |
O2 | 0.0503 (6) | 0.0798 (8) | 0.0421 (6) | 0.0005 (5) | 0.0152 (5) | −0.0147 (5) |
N1 | 0.0376 (6) | 0.0549 (8) | 0.0399 (7) | 0.0001 (5) | 0.0162 (5) | 0.0025 (6) |
C1 | 0.0369 (6) | 0.0420 (8) | 0.0378 (7) | −0.0052 (6) | 0.0159 (5) | 0.0030 (6) |
C2 | 0.0465 (8) | 0.0557 (10) | 0.0433 (8) | −0.0040 (7) | 0.0190 (7) | −0.0014 (7) |
C3 | 0.0664 (10) | 0.0594 (10) | 0.0604 (11) | −0.0070 (8) | 0.0370 (9) | −0.0106 (8) |
C4 | 0.0586 (10) | 0.0493 (10) | 0.0853 (13) | 0.0013 (8) | 0.0438 (9) | 0.0000 (9) |
C5 | 0.0440 (8) | 0.0553 (10) | 0.0696 (11) | 0.0052 (7) | 0.0235 (8) | 0.0109 (8) |
C6 | 0.0408 (7) | 0.0533 (9) | 0.0436 (8) | −0.0018 (7) | 0.0150 (6) | 0.0048 (7) |
C7 | 0.0379 (7) | 0.0458 (8) | 0.0374 (8) | −0.0052 (6) | 0.0156 (5) | 0.0021 (6) |
C8 | 0.0454 (8) | 0.0501 (9) | 0.0583 (10) | 0.0065 (7) | 0.0256 (7) | 0.0099 (8) |
C9 | 0.0447 (7) | 0.0410 (8) | 0.0558 (9) | 0.0018 (6) | 0.0266 (6) | −0.0020 (7) |
C10 | 0.0477 (9) | 0.0840 (14) | 0.0753 (13) | −0.0025 (9) | 0.0209 (8) | 0.0173 (11) |
C11 | 0.0510 (11) | 0.0993 (17) | 0.1074 (18) | −0.0151 (11) | 0.0333 (11) | 0.0117 (13) |
C12 | 0.0808 (13) | 0.0764 (14) | 0.1031 (17) | −0.0141 (11) | 0.0639 (13) | −0.0013 (12) |
C13 | 0.0835 (13) | 0.0814 (14) | 0.0652 (12) | −0.0113 (10) | 0.0464 (10) | 0.0005 (10) |
C14 | 0.0579 (10) | 0.0695 (11) | 0.0538 (10) | −0.0107 (8) | 0.0283 (8) | −0.0039 (8) |
O1—C6 | 1.3506 (18) | C10—C11 | 1.385 (3) |
O2—C7 | 1.2456 (17) | C11—C12 | 1.355 (3) |
O1—HO1 | 0.98 (3) | C12—C13 | 1.360 (4) |
N1—C7 | 1.3311 (19) | C13—C14 | 1.381 (3) |
N1—C8 | 1.466 (2) | C2—H2 | 0.956 (19) |
N1—HN1 | 0.882 (18) | C3—H3 | 0.954 (19) |
C1—C7 | 1.483 (2) | C4—H4 | 0.94 (2) |
C1—C6 | 1.401 (2) | C5—H5 | 0.99 (2) |
C1—C2 | 1.387 (2) | C8—H8A | 1.010 (16) |
C2—C3 | 1.375 (3) | C8—H8B | 0.995 (17) |
C3—C4 | 1.379 (3) | C10—H10 | 0.94 (2) |
C4—C5 | 1.361 (3) | C11—H11 | 0.95 (3) |
C5—C6 | 1.389 (3) | C12—H12 | 0.97 (3) |
C8—C9 | 1.511 (3) | C13—H13 | 0.99 (2) |
C9—C14 | 1.370 (2) | C14—H14 | 0.94 (2) |
C9—C10 | 1.375 (3) | ||
O1···O2 | 2.4886 (19) | C9···H4iv | 3.034 (17) |
O1···N1i | 2.9191 (18) | C14···H4iv | 2.989 (17) |
O2···C14 | 3.260 (3) | HN1···C2 | 2.554 (19) |
O2···O1 | 2.4886 (19) | HN1···H2 | 2.00 (3) |
O1···H2i | 2.58 (2) | HN1···O1iii | 2.083 (18) |
O1···HN1i | 2.083 (18) | H2···N1 | 2.597 (18) |
O2···HO1 | 1.56 (3) | H2···HN1 | 2.00 (3) |
O2···H8A | 2.416 (18) | H2···O1iii | 2.58 (2) |
O2···H14 | 2.59 (2) | HO1···O2 | 1.56 (3) |
O2···H5ii | 2.692 (19) | HO1···C7 | 2.16 (2) |
N1···O1iii | 2.9191 (18) | HO1···H5ii | 2.50 (3) |
N1···H2 | 2.597 (18) | H4···C9iv | 3.034 (17) |
C1···C3iv | 3.554 (2) | H4···C14iv | 2.989 (17) |
C1···C8v | 3.549 (2) | H5···O2vi | 2.692 (19) |
C3···C1iv | 3.554 (2) | H5···HO1vi | 2.50 (3) |
C6···C8v | 3.507 (2) | H8A···O2 | 2.416 (18) |
C7···C7v | 3.400 (2) | H8A···H14 | 2.56 (2) |
C7···C14 | 3.483 (3) | H8A···H13vii | 2.54 (3) |
C8···C1v | 3.549 (2) | H8A···C1v | 3.075 (18) |
C8···C6v | 3.507 (2) | H8A···C2v | 3.060 (18) |
C14···C7 | 3.483 (3) | H8B···H10 | 2.32 (3) |
C14···O2 | 3.260 (3) | H8B···C6v | 3.073 (17) |
C1···H8Av | 3.075 (18) | H10···H8B | 2.32 (3) |
C2···H8Av | 3.060 (18) | H13···H8Aviii | 2.54 (3) |
C2···HN1 | 2.554 (19) | H14···O2 | 2.59 (2) |
C6···H8Bv | 3.073 (17) | H14···C7 | 3.09 (2) |
C7···H14 | 3.09 (2) | H14···H8A | 2.56 (2) |
C7···HO1 | 2.16 (2) | ||
C6—O1—HO1 | 102.3 (13) | C9—C14—C13 | 121.17 (19) |
C7—N1—C8 | 122.74 (13) | C1—C2—H2 | 118.7 (11) |
C7—N1—HN1 | 119.3 (12) | C3—C2—H2 | 119.8 (11) |
C8—N1—HN1 | 117.7 (13) | C2—C3—H3 | 118.8 (12) |
C6—C1—C7 | 118.17 (12) | C4—C3—H3 | 121.6 (12) |
C2—C1—C6 | 117.83 (15) | C3—C4—H4 | 120.2 (11) |
C2—C1—C7 | 124.00 (14) | C5—C4—H4 | 119.2 (11) |
C1—C2—C3 | 121.50 (16) | C4—C5—H5 | 122.9 (12) |
C2—C3—C4 | 119.62 (17) | C6—C5—H5 | 116.9 (12) |
C3—C4—C5 | 120.55 (19) | N1—C8—H8A | 106.4 (11) |
C4—C5—C6 | 120.15 (17) | N1—C8—H8B | 105.6 (11) |
C1—C6—C5 | 120.35 (14) | C9—C8—H8A | 109.4 (10) |
O1—C6—C1 | 121.46 (15) | C9—C8—H8B | 108.8 (11) |
O1—C6—C5 | 118.19 (15) | H8A—C8—H8B | 114.1 (13) |
O2—C7—C1 | 120.79 (13) | C9—C10—H10 | 117.9 (14) |
O2—C7—N1 | 120.61 (14) | C11—C10—H10 | 121.6 (14) |
N1—C7—C1 | 118.60 (12) | C10—C11—H11 | 118.5 (15) |
N1—C8—C9 | 112.64 (13) | C12—C11—H11 | 121.0 (15) |
C8—C9—C10 | 120.97 (16) | C11—C12—H12 | 123.9 (13) |
C8—C9—C14 | 120.74 (16) | C13—C12—H12 | 116.2 (13) |
C10—C9—C14 | 118.28 (18) | C12—C13—H13 | 122.5 (15) |
C9—C10—C11 | 120.3 (2) | C14—C13—H13 | 117.6 (15) |
C10—C11—C12 | 120.5 (2) | C9—C14—H14 | 120.7 (11) |
C11—C12—C13 | 119.9 (2) | C13—C14—H14 | 118.2 (11) |
C12—C13—C14 | 119.8 (2) | ||
C8—N1—C7—O2 | 1.6 (2) | C2—C3—C4—C5 | −0.2 (3) |
C8—N1—C7—C1 | −178.95 (14) | C3—C4—C5—C6 | 0.2 (3) |
C7—N1—C8—C9 | 89.06 (18) | C4—C5—C6—O1 | 179.22 (16) |
C6—C1—C2—C3 | 0.4 (2) | C4—C5—C6—C1 | 0.1 (2) |
C7—C1—C2—C3 | −179.59 (16) | N1—C8—C9—C10 | 104.4 (2) |
C2—C1—C6—O1 | −179.48 (15) | N1—C8—C9—C14 | −74.4 (2) |
C2—C1—C6—C5 | −0.4 (2) | C8—C9—C10—C11 | −179.0 (2) |
C7—C1—C6—O1 | 0.5 (2) | C14—C9—C10—C11 | −0.2 (3) |
C7—C1—C6—C5 | 179.56 (15) | C8—C9—C14—C13 | 178.77 (18) |
C2—C1—C7—O2 | 175.27 (15) | C10—C9—C14—C13 | −0.1 (3) |
C2—C1—C7—N1 | −4.2 (2) | C9—C10—C11—C12 | 0.1 (4) |
C6—C1—C7—O2 | −4.7 (2) | C10—C11—C12—C13 | 0.3 (4) |
C6—C1—C7—N1 | 175.80 (14) | C11—C12—C13—C14 | −0.6 (4) |
C1—C2—C3—C4 | −0.1 (3) | C12—C13—C14—C9 | 0.5 (3) |
Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) −x+1/2, y−1/2, −z−1/2; (iii) x+1/2, −y+3/2, z+1/2; (iv) −x+1, −y+2, −z; (v) −x+1, −y+1, −z; (vi) −x+1/2, y+1/2, −z−1/2; (vii) −x+3/2, y−1/2, −z−1/2; (viii) −x+3/2, y+1/2, −z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—HN1···O1iii | 0.882 (18) | 2.083 (18) | 2.9191 (18) | 158.1 (18) |
O1—HO1···O2 | 0.98 (3) | 1.56 (3) | 2.4886 (19) | 157 (2) |
C2—H2···O1iii | 0.956 (19) | 2.58 (2) | 3.507 (2) | 162.5 (15) |
C14—H14···O2 | 0.94 (2) | 2.59 (2) | 3.260 (3) | 128.8 (14) |
Symmetry code: (iii) x+1/2, −y+3/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H13NO2 |
Mr | 227.25 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 290 |
a, b, c (Å) | 12.478 (3), 8.3503 (17), 12.664 (3) |
β (°) | 118.02 (3) |
V (Å3) | 1164.9 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.33 × 0.22 × 0.20 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.977, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11112, 2665, 1648 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.116, 1.03 |
No. of reflections | 2665 |
No. of parameters | 207 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.17, −0.14 |
Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—HN1···O1i | 0.882 (18) | 2.083 (18) | 2.9191 (18) | 158.1 (18) |
O1—HO1···O2 | 0.98 (3) | 1.56 (3) | 2.4886 (19) | 157 (2) |
C2—H2···O1i | 0.956 (19) | 2.58 (2) | 3.507 (2) | 162.5 (15) |
Symmetry code: (i) x+1/2, −y+3/2, z+1/2. |
Acknowledgements
The authors gratefully acknowledge the financial support of the Education Office of Zhejiang Province (grant No. 20051316).
References
Agwade, V. C. (1982). Chem. Eng. Data, 27, 479–481. Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalStructure. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Over a quater of a century ago (Agwade, 1982) published a thesis on Potential Central Nervous System Active Agents, which included the synthesis of aromatic N-benzyl amides. One of the compounds synthesized was N-benzyl-2-hydroxy-benzamide, (I), whose crystal structure has not been descibed until now.
The molecular structure of compound I is illustrated in Fig. 1. The bond lengths and angles are close to normal values (Allen et al., 1987). There is an intramolecular O-H···O hydrogen bond in the molecule involving the carbonyl O-atom and the 2-hydroxyl substituent (Table 1). The best planes through the benzyl (atoms C8,C9-C14) and the 2-hydoxybenzamide (atoms C1-C6,C7,N1,O1,O2) moieties are inclined to one another by 68.81 (7)°.
In the crystal structure of I symmetry related molecules are connected via an N-H···O hydrogen bond to form chains running along the a direction. These chains are further connected connected via C-H···O hydrogen bonds (Table 1) to form a sheet-like structure (Fig 2).