organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2414-3146

3-(4-Meth­­oxy­phen­yl)-4-methyl-N-[4-(4-methyl­phen­yl)-1,3-thia­zol-2-yl]benzamide

CROSSMARK_Color_square_no_text.svg

aDrug Discovery Lab, Department of Chemistry, Annamalai University, Annamalainagar, Chidambaram 608 002, India, and bPG & Research Department of Physics, Government Arts College, Melur 625 106, India
*Correspondence e-mail: profskabilan@gmail.com

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 11 May 2017; accepted 15 May 2017; online 19 May 2017)

In the title compound, C25H22N2O2S, the methyl­phenyl rings are oriented with a dihedral angle of 19.4 (1)° with respect to each other. In the crystal, mol­ecules are linked via strong N—H⋯O hydrogen bonds, which form C(11) chains propagating along [001]. In addition, weak C—H⋯O and C—H⋯π inter­actions are observed in the structure.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Thia­zole derivatives show USP7 (Chen et al., 2017[Chen, C., Song, J., Wang, J., Xu, C., Chen, C., Gu, W., Sun, H. & Wen, X. (2017). Bioorg. Med. Chem. Lett. 27, 845-849.]), PDE-4 (Balasubramanian et al., 2016[Balasubramanian, G., Narayanan, S., Andiappan, L., Sappanimuthu, T., Thirunavukkarasu, S., Sundaram, S., Natarajan, S., Sivaraman, N., Rajagopal, S., Nazumudeen, F. A., Saxena, S., Vishwakarma, S. L., Narayanan, S., Sharma, G. V., Srinivasan, C. V. & Kilambi, N. (2016). Bioorg. Med. Chem. 24, 5702-5716.]) and Pin1 (Zhao et al., 2016[Zhao, H., Cui, G., Jin, J., Chen, X. & Xu, B. (2016). Bioorg. Med. Chem. 24, 5911-5920.]) inhibitory activities. They possess anti­oxidant (Grozav et al., 2017[Grozav, A., Porumb, I. D., Găină, L. I., Filip, L. & Hanganu, D. (2017). Molecules, 22, 260.]) and anti-Trypanosoma cruzi (da Silva et al., 2017[Silva, E. B. da, Oliveira e Silva, D. A., Oliveira, A. R., da Silva Mendes, C. H., dos Santos, T. A. R., da Silva, A. C., de Castro, M. C. A., Ferreira, R. S., Moreira, D. R. M., Cardoso, M. V. de O., de Simone, C. A., Pereira, V. R. A. & Leite, A. C. L. (2017). Eur. J. Med. Chem. 130, 39-50.]) activities and are used as anti-prostate cancer agents (Saravanan et al., 2017[Saravanan, K., Elancheran, R., Divakar, S., Anand, S. A., Ramanathan, M., Kotoky, J., Lokanath, N. K. & Kabilan, S. (2017). Bioorg. Med. Chem. Lett. 27, 1199-1204.]). In view of the above importance of thia­zole derivatives, we have undertaken the single-crystal X-ray diffraction study of the title compound, and the results are presented herein.

The mol­ecular structure of the title compound is illustrated in Fig. 1[link]. The meth­oxy atoms O2 and C25 deviate by 0.019 (2) and 0.363 (3) Å, respectively, from the attached ring. The methyl phenyl­rings are oriented at a dihedral angle of 19.4 (1)° with respect to each other. The methyl­phenyl ring attached to the thia­zole group is almost perpendicular to the meth­oxy­phenyl ring, making a dihedral angle of 84.2 (1)°.

[Figure 1]
Figure 1
The mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

In the crystal, N—H⋯O hydrogen bonds (Table 1[link]) link the mol­ecules, forming C(11) chains propagating along [100]. Two C—H⋯O inter­actions link the mol­ecules, forming C(10) and C(12) chains (Fig. 2[link]). In addition, C—H⋯π inter­actions link the mol­ecules into C(13) chains propagating along [010] (Table 1[link] and Fig. 3[link]).

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C12–C17 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2⋯O2i 0.86 2.33 3.175 (2) 166
C7—H7B⋯O1i 0.96 2.59 3.452 (3) 149
C13—H13⋯O2i 0.93 2.50 3.413 (4) 166
C7—H7CCgii 0.96 2.67 3.592 (5) 149
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].
[Figure 2]
Figure 2
The crystal packing of the title compound viewed down b axis. The N—H⋯O and C—H⋯O hydrogen bonds are shown as dashed lines (see Table 1[link]). For clarity H atoms not involved in these hydrogen bonds have been omitted.
[Figure 3]
Figure 3
The crystal packing of the title compound. The weak C—H⋯π inter­actions (see Table 1[link]) are shown as dashed lines. For clarity H atoms not involved in these inter­actions have been omitted.

Synthesis and crystallization

3-Iodo-4-methyl-N-(4-(p-tol­yl)thia­zol-2-yl)benzamide (0.23 mmol) was dissolved in 20 ml of de­oxy­genated toluene and water (8:2). Then, tetra­kis­(tri­phenyl­phosphine)palladium (0.017 mmol) and K2CO3 (0.72 mmol) was added in turn at 10 minute inter­vals. Finally, 4-meth­oxy phenyl boronic acid (0.25 mmol) was added and the resulting reaction mixture was heated to reflux for 16 h under a nitro­gen atmosphere. The progress of the reaction was monitored by pre-coated TLC plates. After completion of the reaction, it was cooled to rt and concentrated using a Rotavac. The obtained crude compound was purified by column chromatography using 20% ethyl acetate and petroleum ether (60:80) as eluent. The pure compound was obtained as a yellow solid, which was recrystallized from a methanol solution, yielding yellow crystals.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C25H22N2O2S
Mr 414.50
Crystal system, space group Monoclinic, P21/c
Temperature (K) 296
a, b, c (Å) 9.784 (1), 10.291 (1), 21.58 (2)
β (°) 99.528 (11)
V3) 2143 (2)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.18
Crystal size (mm) 0.22 × 0.20 × 0.18
 
Data collection
Diffractometer Bruker SMART APEX CCD area-detector
No. of measured, independent and observed [I > 2σ(I)] reflections 7733, 4741, 3399
Rint 0.050
(sin θ/λ)max−1) 0.648
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.178, 1.06
No. of reflections 4741
No. of parameters 273
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.28, −0.26
Computer programs: SMART and SAINT (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Structural data


Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

3-(4-Methoxyphenyl)-4-methyl-N-[4-(4-methylphenyl)-1,3-thiazol-2-yl]benzamide top
Crystal data top
C25H22N2O2SF(000) = 872
Mr = 414.50Dx = 1.285 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.784 (1) ÅCell parameters from 5988 reflections
b = 10.291 (1) Åθ = 3.3–26.9°
c = 21.58 (2) ŵ = 0.18 mm1
β = 99.528 (11)°T = 296 K
V = 2143 (2) Å3Block, yellow
Z = 40.22 × 0.20 × 0.18 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
Rint = 0.050
Radiation source: fine-focus sealed tubeθmax = 27.4°, θmin = 3.1°
ω and φ scansh = 812
7733 measured reflectionsk = 137
4741 independent reflectionsl = 2727
3399 reflections with I > 2σ(I)
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.178 w = 1/[σ2(Fo2) + (0.0938P)2 + 0.3624P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
4741 reflectionsΔρmax = 0.28 e Å3
273 parametersΔρmin = 0.26 e Å3
Special details top

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. All H atoms were found in a difference map, but refined as riding on their parent atom with Uiso(H) = 1.2Ueq(C,N) or Uiso(H) = 1.5Ueq(Cmethyl).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.15473 (6)0.72428 (6)0.08785 (3)0.0600 (2)
O10.32225 (19)0.7510 (2)0.00108 (9)0.0804 (6)
O20.67000 (17)0.99059 (14)0.32054 (6)0.0536 (4)
N10.31758 (17)0.60345 (16)0.17559 (7)0.0438 (4)
N20.42415 (19)0.64619 (18)0.08819 (7)0.0490 (4)
H20.49800.60850.10690.059*
C10.3007 (2)0.5388 (2)0.30297 (9)0.0450 (5)
H10.38650.54140.28980.054*
C20.2926 (2)0.4998 (2)0.36389 (10)0.0488 (5)
H2A0.37330.47590.39060.059*
C30.1669 (2)0.4955 (2)0.38611 (11)0.0508 (5)
C40.0493 (2)0.5281 (3)0.34400 (12)0.0626 (6)
H40.03670.52350.35690.075*
C50.0560 (2)0.5675 (2)0.28275 (12)0.0596 (6)
H50.02510.58970.25590.072*
C60.1821 (2)0.57396 (19)0.26133 (9)0.0424 (4)
C70.1594 (3)0.4598 (3)0.45323 (12)0.0701 (7)
H7A0.06670.43340.45640.105*
H7B0.18450.53370.47980.105*
H7C0.22220.38960.46620.105*
C80.1929 (2)0.62106 (19)0.19730 (10)0.0436 (4)
C90.0947 (2)0.6840 (2)0.15596 (11)0.0578 (6)
H90.00610.70290.16360.069*
C100.3109 (2)0.6522 (2)0.11926 (9)0.0447 (5)
C110.4253 (2)0.6969 (2)0.02931 (10)0.0527 (5)
C120.5550 (2)0.6842 (2)0.00231 (9)0.0470 (5)
C130.6709 (2)0.6125 (2)0.02920 (10)0.0537 (5)
H130.67090.56950.06710.064*
C140.7854 (2)0.6052 (2)0.00029 (10)0.0547 (6)
H140.86140.55680.01840.066*
C150.7917 (2)0.6682 (2)0.05762 (9)0.0480 (5)
C160.6745 (2)0.74095 (19)0.08500 (9)0.0431 (5)
C170.5605 (2)0.7478 (2)0.05473 (9)0.0463 (5)
H170.48440.79670.07300.056*
C180.9212 (2)0.6606 (3)0.08627 (11)0.0611 (6)
H18A0.99680.63160.05520.092*
H18B0.94210.74490.10120.092*
H18C0.90750.60040.12070.092*
C190.6722 (2)0.81014 (19)0.14646 (9)0.0417 (4)
C200.67264 (19)0.94456 (19)0.14980 (8)0.0413 (4)
H200.67350.99290.11330.050*
C210.6718 (2)1.00913 (19)0.20683 (9)0.0420 (4)
H210.67251.09950.20820.050*
C220.6699 (2)0.93737 (19)0.26148 (8)0.0416 (4)
C230.6675 (2)0.8030 (2)0.25930 (9)0.0513 (5)
H230.66510.75470.29590.062*
C240.6687 (3)0.7411 (2)0.20230 (10)0.0537 (6)
H240.66700.65070.20120.064*
C250.7070 (3)1.1241 (2)0.32305 (11)0.0667 (7)
H25A0.70341.14980.36610.100*
H25B0.64321.17600.30420.100*
H25C0.79921.13660.30050.100*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0555 (4)0.0667 (4)0.0542 (3)0.0144 (3)0.0015 (3)0.0113 (3)
O10.0677 (11)0.1073 (15)0.0668 (11)0.0306 (11)0.0131 (9)0.0386 (10)
O20.0766 (10)0.0462 (8)0.0363 (7)0.0113 (7)0.0042 (7)0.0045 (6)
N10.0419 (9)0.0447 (9)0.0435 (8)0.0004 (7)0.0031 (7)0.0033 (7)
N20.0485 (10)0.0557 (10)0.0415 (9)0.0047 (9)0.0039 (7)0.0085 (8)
C10.0364 (10)0.0488 (11)0.0505 (10)0.0007 (9)0.0091 (8)0.0025 (9)
C20.0443 (11)0.0507 (12)0.0505 (11)0.0017 (9)0.0058 (9)0.0015 (9)
C30.0552 (12)0.0415 (11)0.0589 (12)0.0073 (10)0.0190 (10)0.0024 (9)
C40.0434 (12)0.0724 (16)0.0771 (16)0.0024 (12)0.0246 (11)0.0076 (13)
C50.0366 (11)0.0707 (15)0.0708 (14)0.0006 (11)0.0065 (10)0.0082 (12)
C60.0381 (10)0.0383 (10)0.0509 (11)0.0020 (8)0.0074 (8)0.0036 (8)
C70.0817 (18)0.0700 (16)0.0644 (15)0.0114 (14)0.0290 (13)0.0041 (12)
C80.0409 (10)0.0388 (10)0.0498 (10)0.0011 (8)0.0037 (8)0.0044 (8)
C90.0474 (12)0.0643 (14)0.0600 (13)0.0090 (11)0.0036 (10)0.0034 (11)
C100.0464 (11)0.0398 (10)0.0456 (10)0.0017 (9)0.0009 (8)0.0007 (8)
C110.0588 (13)0.0518 (12)0.0460 (11)0.0047 (11)0.0047 (10)0.0109 (9)
C120.0531 (12)0.0446 (11)0.0419 (10)0.0018 (10)0.0032 (9)0.0059 (8)
C130.0625 (14)0.0533 (12)0.0434 (10)0.0096 (11)0.0031 (9)0.0151 (9)
C140.0562 (13)0.0546 (13)0.0504 (12)0.0138 (11)0.0007 (10)0.0119 (10)
C150.0532 (12)0.0428 (10)0.0453 (10)0.0035 (10)0.0001 (9)0.0020 (8)
C160.0499 (11)0.0383 (10)0.0389 (9)0.0001 (9)0.0010 (8)0.0024 (8)
C170.0507 (11)0.0442 (11)0.0413 (10)0.0060 (9)0.0008 (8)0.0065 (8)
C180.0548 (13)0.0663 (15)0.0605 (13)0.0091 (12)0.0043 (10)0.0107 (11)
C190.0421 (10)0.0423 (10)0.0383 (9)0.0001 (9)0.0003 (8)0.0043 (8)
C200.0428 (10)0.0428 (10)0.0364 (9)0.0033 (9)0.0010 (7)0.0020 (7)
C210.0451 (10)0.0372 (9)0.0415 (10)0.0046 (8)0.0011 (8)0.0009 (7)
C220.0423 (10)0.0431 (10)0.0369 (9)0.0045 (9)0.0006 (7)0.0034 (7)
C230.0716 (14)0.0419 (11)0.0387 (10)0.0002 (10)0.0044 (9)0.0040 (8)
C240.0768 (15)0.0371 (10)0.0453 (11)0.0038 (11)0.0048 (10)0.0018 (8)
C250.0946 (19)0.0514 (13)0.0512 (12)0.0145 (13)0.0039 (12)0.0105 (10)
Geometric parameters (Å, º) top
S1—C91.721 (3)C12—C131.396 (3)
S1—C101.732 (2)C12—C171.403 (3)
O1—C111.223 (3)C13—C141.379 (3)
O2—C221.387 (2)C13—H130.9300
O2—C251.424 (3)C14—C151.407 (3)
N1—C101.307 (3)C14—H140.9300
N1—C81.389 (3)C15—C161.414 (3)
N2—C111.375 (3)C15—C181.501 (3)
N2—C101.388 (3)C16—C171.385 (3)
N2—H20.8600C16—C191.502 (3)
C1—C21.389 (3)C17—H170.9300
C1—C61.393 (3)C18—H18A0.9600
C1—H10.9300C18—H18B0.9600
C2—C31.392 (3)C18—H18C0.9600
C2—H2A0.9300C19—C201.385 (3)
C3—C41.384 (3)C19—C241.395 (3)
C3—C71.508 (3)C20—C211.398 (3)
C4—C51.394 (4)C20—H200.9300
C4—H40.9300C21—C221.389 (3)
C5—C61.389 (3)C21—H210.9300
C5—H50.9300C22—C231.384 (3)
C6—C81.484 (3)C23—C241.384 (3)
C7—H7A0.9600C23—H230.9300
C7—H7B0.9600C24—H240.9300
C7—H7C0.9600C25—H25A0.9600
C8—C91.362 (3)C25—H25B0.9600
C9—H90.9300C25—H25C0.9600
C11—C121.487 (3)
C9—S1—C1088.06 (11)C14—C13—C12120.19 (19)
C22—O2—C25117.04 (16)C14—C13—H13119.9
C10—N1—C8110.62 (17)C12—C13—H13119.9
C11—N2—C10123.95 (18)C13—C14—C15122.5 (2)
C11—N2—H2118.0C13—C14—H14118.7
C10—N2—H2118.0C15—C14—H14118.7
C2—C1—C6120.91 (19)C14—C15—C16117.4 (2)
C2—C1—H1119.5C14—C15—C18120.07 (19)
C6—C1—H1119.5C16—C15—C18122.44 (19)
C1—C2—C3121.8 (2)C17—C16—C15119.38 (18)
C1—C2—H2A119.1C17—C16—C19119.78 (17)
C3—C2—H2A119.1C15—C16—C19120.83 (18)
C4—C3—C2116.9 (2)C16—C17—C12122.73 (19)
C4—C3—C7121.5 (2)C16—C17—H17118.6
C2—C3—C7121.7 (2)C12—C17—H17118.6
C3—C4—C5121.9 (2)C15—C18—H18A109.5
C3—C4—H4119.1C15—C18—H18B109.5
C5—C4—H4119.1H18A—C18—H18B109.5
C6—C5—C4120.9 (2)C15—C18—H18C109.5
C6—C5—H5119.6H18A—C18—H18C109.5
C4—C5—H5119.6H18B—C18—H18C109.5
C5—C6—C1117.6 (2)C20—C19—C24117.65 (17)
C5—C6—C8121.95 (19)C20—C19—C16121.30 (17)
C1—C6—C8120.38 (18)C24—C19—C16121.05 (18)
C3—C7—H7A109.5C19—C20—C21121.39 (17)
C3—C7—H7B109.5C19—C20—H20119.3
H7A—C7—H7B109.5C21—C20—H20119.3
C3—C7—H7C109.5C22—C21—C20119.49 (18)
H7A—C7—H7C109.5C22—C21—H21120.3
H7B—C7—H7C109.5C20—C21—H21120.3
C9—C8—N1113.87 (19)C23—C22—O2115.35 (17)
C9—C8—C6127.9 (2)C23—C22—C21120.02 (17)
N1—C8—C6118.23 (17)O2—C22—C21124.63 (18)
C8—C9—S1111.76 (18)C24—C23—C22119.52 (18)
C8—C9—H9124.1C24—C23—H23120.2
S1—C9—H9124.1C22—C23—H23120.2
N1—C10—N2120.73 (18)C23—C24—C19121.90 (19)
N1—C10—S1115.69 (16)C23—C24—H24119.0
N2—C10—S1123.58 (15)C19—C24—H24119.0
O1—C11—N2120.1 (2)O2—C25—H25A109.5
O1—C11—C12122.10 (19)O2—C25—H25B109.5
N2—C11—C12117.83 (18)H25A—C25—H25B109.5
C13—C12—C17117.7 (2)O2—C25—H25C109.5
C13—C12—C11124.79 (19)H25A—C25—H25C109.5
C17—C12—C11117.51 (18)H25B—C25—H25C109.5
C6—C1—C2—C30.7 (3)N2—C11—C12—C17173.44 (19)
C1—C2—C3—C42.0 (3)C17—C12—C13—C140.4 (3)
C1—C2—C3—C7176.8 (2)C11—C12—C13—C14178.9 (2)
C2—C3—C4—C52.0 (4)C12—C13—C14—C150.1 (4)
C7—C3—C4—C5176.7 (2)C13—C14—C15—C160.0 (3)
C3—C4—C5—C60.8 (4)C13—C14—C15—C18177.8 (2)
C4—C5—C6—C10.5 (4)C14—C15—C16—C170.3 (3)
C4—C5—C6—C8177.3 (2)C18—C15—C16—C17177.5 (2)
C2—C1—C6—C50.6 (3)C14—C15—C16—C19179.44 (19)
C2—C1—C6—C8177.27 (18)C18—C15—C16—C192.8 (3)
C10—N1—C8—C90.2 (3)C15—C16—C17—C120.6 (3)
C10—N1—C8—C6178.77 (17)C19—C16—C17—C12179.12 (18)
C5—C6—C8—C912.7 (3)C13—C12—C17—C160.7 (3)
C1—C6—C8—C9165.1 (2)C11—C12—C17—C16178.67 (19)
C5—C6—C8—N1168.9 (2)C17—C16—C19—C2068.2 (3)
C1—C6—C8—N113.3 (3)C15—C16—C19—C20112.0 (2)
N1—C8—C9—S10.1 (2)C17—C16—C19—C24111.3 (2)
C6—C8—C9—S1178.31 (16)C15—C16—C19—C2468.4 (3)
C10—S1—C9—C80.28 (18)C24—C19—C20—C211.0 (3)
C8—N1—C10—N2179.78 (17)C16—C19—C20—C21179.41 (17)
C8—N1—C10—S10.4 (2)C19—C20—C21—C220.3 (3)
C11—N2—C10—N1179.10 (19)C25—O2—C22—C23164.7 (2)
C11—N2—C10—S10.2 (3)C25—O2—C22—C2115.3 (3)
C9—S1—C10—N10.40 (18)C20—C21—C22—C230.6 (3)
C9—S1—C10—N2179.77 (19)C20—C21—C22—O2179.45 (18)
C10—N2—C11—O10.1 (4)O2—C22—C23—C24179.3 (2)
C10—N2—C11—C12179.34 (19)C21—C22—C23—C240.7 (3)
O1—C11—C12—C13173.2 (2)C22—C23—C24—C190.0 (4)
N2—C11—C12—C137.3 (3)C20—C19—C24—C230.9 (3)
O1—C11—C12—C176.0 (3)C16—C19—C24—C23179.5 (2)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C12–C17 ring.
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.862.333.175 (2)166
C7—H7B···O1i0.962.593.452 (3)149
C13—H13···O2i0.932.503.413 (4)166
C7—H7C···Cgii0.962.673.592 (5)149
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x+1, y1/2, z+1/2.
 

Footnotes

Additional correspondence author, e-mail: s_selvanayagam@rediffmail.com.

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