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

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ISSN: 2414-3146

4,6-Di-tert-butyl-2-{(E)-[4-(di­methyl­amino)­phenyl­imino]­meth­yl}­phenol

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aDepartment of Chemistry, Vaigai College of Engineering, Madurai 625 122, Tamil Nadu, India, bDepartment of Chemistry, University of Pitesti, Pitesti-11040, Romania, cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and dPG & Research Department of Chemistry, Chikkanna Government Arts College, Tiruppur 641 602, Tamil Nadu, India
*Correspondence e-mail: chakkaravarthi_2005@yahoo.com, rajagopal18@yahoo.com

Edited by L. Van Meervelt, Katholieke Universiteit Leuven, Belgium (Received 7 March 2017; accepted 11 March 2017; online 17 March 2017)

The title compound, C23H32N2O, adopts an E conformation about the C=N bond. The dihedral angle between the aromatic rings is 25.39 (14)°. One of the tert-butyl groups has rotational disorder, with site occupancies of 0.716 (3) and 0.284 (3). An intra­molecular O—H⋯N hydrogen bond is present, forming an S(6) ring motif.

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

Structure description

Schiff bases have attracted much attention for their biological properties such as anti-bacterial, anti-cancer and anti­tumor (Ida Malarselvi et al., 2016[Ida Malarselvi, R., Ramachandra Raja, C., Priscilla, J. & Viswanathan, K. (2016). Materials Today: Proceedings, 3, 1444-1450.]; Khattab, 2005[Khattab, S. N. (2005). Molecules, 10, 1218-1228.]; Karthikeyan et al., 2006[Karthikeyan, M. S., Prasad, D. J., Poojary, B., Bhat, K. S., Holla, B. S. & Kumari, N. S. (2006). Bioorg. Med. Chem. 14, 7482-7489.]). We herein report the crystal structure of title compound, which contains a C=N bond (Fig. 1[link]).

[Figure 1]
Figure 1
The mol­ecular structure of the title compound, with the atom labelling and 30% probability displacement ellipsoids. The intra­molecular O1—H1⋯N2 hydrogen bond is shown as a dashed line.

Bond lengths in the title compound are comparable with those in a similar structure (Fun et al., 2013[Fun, H.-K., Chantrapromma, S., Nilwanna, B., Kobkeatthawin, T. & Boonnak, N. (2013). Acta Cryst. E69, o1203-o1204.]). The dihedral angle between the aromatic rings (C3–C8 and C10–C15) is 25.39 (14)°. The conformation of the C=N (C9=N2) bond of this Schiff base is E and the intra­molecular O1—H1⋯N2 hydrogen bond forms an S(6) ring-motif (Fig. 1[link] and Table 1[link]). There are no significant inter­molecular inter­actions beyond normal van der Waals contacts present in the crystal structure.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯N2 0.83 (1) 1.78 (2) 2.544 (3) 153 (4)

Synthesis and crystallization

An ethano­lic solution of N,N–dimethyl-1,4-phenyl­enedi­amine (5 mmol) was stirred magnetically in a round-bottom flask followed by dropwise addition of 3,5-di-tert-butyl-2-hy­droxy­benzaldehyde (5 mmol) containing 2–3 drops of glacial acetic acid. The reaction mixture was stirred for 1 h and then refluxed for 2–3 h. Upon cooling to room temperature, the yellow precipitate formed was filtered and dried in vacuo over anhydrous calcium chloride. Single crystals suitable for X–ray diffraction were obtained by slow evaporation of a solution of the title compound in di­methyl­formamide at room temperature.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. One of the tert-butyl groups shows rotational disorder with major components of C21, C22 and C23 having site occupancies 0.716 (3) and minor components of C21′, C22′ and C23′ site occupancies of 0.284 (3). The anisotropic displacement parameters of the disordered C atoms were restrained by SIMU instructions within 0.001 as standard deviations. Rigid-bond restraints were applied for bonds C20—C21, C20—C21′, C20—C22, C20—C22′, C20—C23 and C20—C23′ with a standard deviation of 0.001 using the DELU instruction during the final cycles of the SHELXL refinement.

Table 2
Experimental details

Crystal data
Chemical formula C23H32N2O
Mr 352.50
Crystal system, space group Monoclinic, P21/c
Temperature (K) 295
a, b, c (Å) 22.8029 (15), 9.9908 (7), 9.3304 (6)
β (°) 90.247 (2)
V3) 2125.6 (2)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.07
Crystal size (mm) 0.34 × 0.28 × 0.24
 
Data collection
Diffractometer Bruker Kappa APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.917, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections 35692, 4143, 2643
Rint 0.041
(sin θ/λ)max−1) 0.615
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.070, 0.215, 1.03
No. of reflections 4143
No. of parameters 277
No. of restraints 49
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.48, −0.40
Computer programs: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2016/4 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Structural data


Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016/4 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2016/4 (Sheldrick, 2015) and PLATON (Spek, 2009).

4,6-Di-tert-butyl-2-{(E)-[4-(dimethylamino)phenylimino]methyl}phenol top
Crystal data top
C23H32N2OF(000) = 768
Mr = 352.50Dx = 1.102 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 22.8029 (15) ÅCell parameters from 5165 reflections
b = 9.9908 (7) Åθ = 2.4–22.4°
c = 9.3304 (6) ŵ = 0.07 mm1
β = 90.247 (2)°T = 295 K
V = 2125.6 (2) Å3Block, colourless
Z = 40.34 × 0.28 × 0.24 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
2643 reflections with I > 2σ(I)
ω and φ scanRint = 0.041
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
θmax = 25.9°, θmin = 2.2°
Tmin = 0.917, Tmax = 0.980h = 2728
35692 measured reflectionsk = 1211
4143 independent reflectionsl = 1111
Refinement top
Refinement on F249 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.070H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.215 w = 1/[σ2(Fo2) + (0.0826P)2 + 1.5721P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
4143 reflectionsΔρmax = 0.48 e Å3
277 parametersΔρmin = 0.40 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C11.08947 (15)0.2191 (4)0.4437 (5)0.1011 (13)
H1A1.0587330.2105910.3736320.152*
H1B1.1262620.1951250.4011630.152*
H1C1.0912600.3100010.4768350.152*
C21.12567 (14)0.0568 (6)0.6207 (4)0.1144 (16)
H2A1.1337630.0868930.7165270.172*
H2B1.1597630.0697310.5623510.172*
H2C1.1156470.0364930.6224520.172*
C31.02298 (11)0.1250 (3)0.6223 (3)0.0639 (8)
C40.97629 (11)0.2029 (3)0.5733 (3)0.0680 (8)
H40.9823420.2619910.4978080.082*
C50.92141 (11)0.1945 (3)0.6339 (3)0.0636 (8)
H50.8912520.2480870.5987140.076*
C60.91044 (10)0.1079 (3)0.7460 (3)0.0551 (7)
C70.95692 (12)0.0327 (4)0.7962 (3)0.0718 (9)
H70.9509770.0249170.8730170.086*
C81.01151 (12)0.0404 (4)0.7364 (4)0.0760 (9)
H81.0416000.0124040.7731950.091*
C90.80644 (11)0.1125 (3)0.7538 (3)0.0558 (7)
H90.8057820.1529800.6640840.067*
C100.75150 (10)0.0801 (3)0.8222 (3)0.0506 (6)
C110.75054 (10)0.0212 (3)0.9600 (3)0.0513 (6)
C120.69728 (11)0.0174 (3)1.0215 (3)0.0495 (6)
C130.64680 (11)0.0056 (2)0.9426 (3)0.0498 (6)
H130.6112100.0195590.9827770.060*
C140.64568 (10)0.0639 (3)0.8067 (3)0.0485 (6)
C150.69883 (11)0.1005 (3)0.7497 (3)0.0518 (6)
H150.6995730.1402230.6595330.062*
C160.69585 (11)0.0847 (3)1.1696 (3)0.0571 (7)
C170.63306 (13)0.1193 (4)1.2142 (3)0.0757 (9)
H17A0.6104190.0386201.2215500.114*
H17B0.6337540.1638971.3053610.114*
H17C0.6156730.1771201.1436870.114*
C180.72105 (13)0.0092 (3)1.2834 (3)0.0706 (8)
H18A0.6973270.0883511.2889460.106*
H18B0.7604120.0333751.2580660.106*
H18C0.7212710.0352101.3746420.106*
C190.73069 (15)0.2162 (3)1.1661 (4)0.0806 (10)
H19A0.7141460.2746311.0949360.121*
H19B0.7288530.2585751.2583160.121*
H19C0.7708360.1976241.1428140.121*
C200.58838 (12)0.0852 (3)0.7249 (3)0.0675 (7)
C210.5923 (2)0.0156 (6)0.5802 (5)0.0822 (9)0.716 (3)
H21A0.5975450.0788320.5944980.123*0.716 (3)
H21B0.6249500.0507320.5277290.123*0.716 (3)
H21C0.5567540.0308640.5270230.123*0.716 (3)
C220.53550 (19)0.0335 (6)0.8033 (6)0.0861 (9)0.716 (3)
H22A0.5325180.0775760.8944480.129*0.716 (3)
H22B0.5393950.0612070.8179450.129*0.716 (3)
H22C0.5008390.0511510.7477060.129*0.716 (3)
C230.5796 (2)0.2327 (5)0.6985 (6)0.0825 (8)0.716 (3)
H23A0.5439950.2461610.6451210.124*0.716 (3)
H23B0.6121230.2671890.6450410.124*0.716 (3)
H23C0.5770390.2786410.7886430.124*0.716 (3)
C21'0.5948 (5)0.1512 (14)0.5788 (13)0.0814 (10)0.284 (3)
H21D0.6102430.2399130.5907140.122*0.284 (3)
H21E0.5571360.1559380.5327130.122*0.284 (3)
H21F0.6210630.0994020.5208750.122*0.284 (3)
C22'0.5506 (5)0.0439 (14)0.7261 (14)0.0827 (10)0.284 (3)
H22D0.5684560.1102740.6660510.124*0.284 (3)
H22E0.5119930.0239110.6906900.124*0.284 (3)
H22F0.5479800.0773360.8223030.124*0.284 (3)
C23'0.5480 (5)0.1814 (14)0.8104 (14)0.0835 (10)0.284 (3)
H23D0.5325630.1355130.8923000.125*0.284 (3)
H23E0.5162960.2106020.7500550.125*0.284 (3)
H23F0.5702930.2576900.8415820.125*0.284 (3)
N11.07772 (10)0.1318 (4)0.5625 (3)0.0886 (9)
N20.85586 (9)0.0874 (2)0.8129 (2)0.0592 (6)
O10.80132 (8)0.0006 (2)1.0312 (2)0.0705 (6)
H10.8283 (12)0.023 (4)0.977 (3)0.106*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.074 (2)0.102 (3)0.127 (3)0.029 (2)0.037 (2)0.010 (3)
C20.0412 (17)0.202 (5)0.100 (3)0.016 (2)0.0014 (17)0.016 (3)
C30.0391 (14)0.083 (2)0.0700 (18)0.0094 (13)0.0000 (12)0.0063 (16)
C40.0483 (16)0.073 (2)0.083 (2)0.0119 (14)0.0013 (14)0.0103 (16)
C50.0416 (14)0.0618 (17)0.087 (2)0.0043 (12)0.0048 (13)0.0078 (15)
C60.0401 (13)0.0642 (17)0.0610 (16)0.0062 (12)0.0004 (11)0.0003 (13)
C70.0488 (16)0.096 (2)0.0704 (19)0.0013 (15)0.0033 (14)0.0174 (17)
C80.0433 (16)0.101 (2)0.083 (2)0.0071 (16)0.0050 (14)0.0108 (19)
C90.0453 (14)0.0645 (17)0.0576 (15)0.0033 (12)0.0020 (12)0.0026 (13)
C100.0414 (13)0.0557 (15)0.0546 (15)0.0011 (11)0.0015 (11)0.0016 (12)
C110.0398 (13)0.0596 (16)0.0545 (15)0.0038 (11)0.0031 (11)0.0009 (12)
C120.0442 (13)0.0511 (14)0.0532 (14)0.0035 (11)0.0023 (11)0.0002 (11)
C130.0409 (13)0.0522 (15)0.0564 (15)0.0003 (11)0.0036 (11)0.0003 (12)
C140.0404 (13)0.0507 (14)0.0542 (14)0.0012 (11)0.0009 (10)0.0031 (12)
C150.0468 (14)0.0579 (15)0.0509 (14)0.0004 (12)0.0007 (11)0.0049 (12)
C160.0509 (15)0.0645 (17)0.0560 (15)0.0050 (12)0.0022 (12)0.0095 (13)
C170.0686 (19)0.090 (2)0.0683 (19)0.0068 (17)0.0074 (15)0.0199 (17)
C180.0682 (19)0.087 (2)0.0563 (16)0.0071 (16)0.0006 (14)0.0030 (16)
C190.086 (2)0.071 (2)0.085 (2)0.0158 (17)0.0063 (18)0.0200 (17)
C200.0441 (13)0.0855 (16)0.0729 (14)0.0065 (11)0.0171 (11)0.0013 (12)
C210.0651 (17)0.1021 (19)0.0793 (16)0.0051 (16)0.0191 (14)0.0090 (15)
C220.0555 (16)0.110 (2)0.0928 (19)0.0010 (15)0.0086 (14)0.0015 (17)
C230.0651 (17)0.0909 (16)0.0915 (19)0.0160 (15)0.0152 (15)0.0033 (14)
C21'0.0663 (19)0.098 (2)0.0800 (17)0.0095 (18)0.0167 (16)0.0046 (16)
C22'0.0594 (19)0.0997 (19)0.089 (2)0.0054 (15)0.0166 (18)0.0035 (16)
C23'0.0588 (19)0.100 (2)0.0918 (19)0.0149 (16)0.0090 (16)0.0028 (18)
N10.0407 (13)0.133 (3)0.092 (2)0.0062 (15)0.0079 (13)0.0055 (19)
N20.0405 (12)0.0713 (15)0.0658 (14)0.0034 (10)0.0007 (10)0.0042 (12)
O10.0411 (10)0.1058 (17)0.0646 (13)0.0038 (10)0.0043 (9)0.0183 (11)
Geometric parameters (Å, º) top
C1—N11.437 (5)C16—C191.536 (4)
C1—H1A0.9600C17—H17A0.9600
C1—H1B0.9600C17—H17B0.9600
C1—H1C0.9600C17—H17C0.9600
C2—N11.431 (5)C18—H18A0.9600
C2—H2A0.9600C18—H18B0.9600
C2—H2B0.9600C18—H18C0.9600
C2—H2C0.9600C19—H19A0.9600
C3—N11.371 (3)C19—H19B0.9600
C3—C81.385 (4)C19—H19C0.9600
C3—C41.394 (4)C20—C221.505 (6)
C4—C51.378 (4)C20—C231.507 (6)
C4—H40.9300C20—C211.522 (6)
C5—C61.381 (4)C20—C21'1.522 (12)
C5—H50.9300C20—C22'1.551 (13)
C6—C71.379 (4)C20—C23'1.554 (12)
C6—N21.410 (3)C21—H21A0.9600
C7—C81.368 (4)C21—H21B0.9600
C7—H70.9300C21—H21C0.9600
C8—H80.9300C22—H22A0.9600
C9—N21.277 (3)C22—H22B0.9600
C9—C101.445 (3)C22—H22C0.9600
C9—H90.9300C23—H23A0.9600
C10—C151.391 (3)C23—H23B0.9600
C10—C111.414 (4)C23—H23C0.9600
C11—O11.348 (3)C21'—H21D0.9600
C11—C121.400 (3)C21'—H21E0.9600
C12—C131.383 (3)C21'—H21F0.9600
C12—C161.537 (4)C22'—H22D0.9600
C13—C141.395 (4)C22'—H22E0.9600
C13—H130.9300C22'—H22F0.9600
C14—C151.375 (3)C23'—H23D0.9600
C14—C201.526 (3)C23'—H23E0.9600
C15—H150.9300C23'—H23F0.9600
C16—C181.527 (4)O1—H10.830 (10)
C16—C171.532 (4)
N1—C1—H1A109.5C16—C18—H18B109.5
N1—C1—H1B109.5H18A—C18—H18B109.5
H1A—C1—H1B109.5C16—C18—H18C109.5
N1—C1—H1C109.5H18A—C18—H18C109.5
H1A—C1—H1C109.5H18B—C18—H18C109.5
H1B—C1—H1C109.5C16—C19—H19A109.5
N1—C2—H2A109.5C16—C19—H19B109.5
N1—C2—H2B109.5H19A—C19—H19B109.5
H2A—C2—H2B109.5C16—C19—H19C109.5
N1—C2—H2C109.5H19A—C19—H19C109.5
H2A—C2—H2C109.5H19B—C19—H19C109.5
H2B—C2—H2C109.5C22—C20—C23108.0 (3)
N1—C3—C8121.2 (3)C22—C20—C21109.0 (3)
N1—C3—C4122.3 (3)C23—C20—C21108.1 (4)
C8—C3—C4116.5 (2)C22—C20—C14113.3 (3)
C5—C4—C3121.7 (3)C23—C20—C14109.3 (3)
C5—C4—H4119.2C21—C20—C14109.1 (3)
C3—C4—H4119.2C21'—C20—C14115.0 (5)
C4—C5—C6121.1 (3)C21'—C20—C22'115.0 (7)
C4—C5—H5119.5C14—C20—C22'110.8 (5)
C6—C5—H5119.5C21'—C20—C23'104.5 (7)
C7—C6—C5117.2 (2)C14—C20—C23'109.7 (5)
C7—C6—N2116.7 (3)C22'—C20—C23'100.4 (7)
C5—C6—N2126.1 (2)C20—C21—H21A109.5
C8—C7—C6122.0 (3)C20—C21—H21B109.5
C8—C7—H7119.0H21A—C21—H21B109.5
C6—C7—H7119.0C20—C21—H21C109.5
C7—C8—C3121.5 (3)H21A—C21—H21C109.5
C7—C8—H8119.3H21B—C21—H21C109.5
C3—C8—H8119.3C20—C22—H22A109.5
N2—C9—C10122.1 (3)C20—C22—H22B109.5
N2—C9—H9119.0H22A—C22—H22B109.5
C10—C9—H9119.0C20—C22—H22C109.5
C15—C10—C11119.1 (2)H22A—C22—H22C109.5
C15—C10—C9120.1 (2)H22B—C22—H22C109.5
C11—C10—C9120.8 (2)C20—C23—H23A109.5
O1—C11—C12120.0 (2)C20—C23—H23B109.5
O1—C11—C10119.7 (2)H23A—C23—H23B109.5
C12—C11—C10120.3 (2)C20—C23—H23C109.5
C13—C12—C11117.2 (2)H23A—C23—H23C109.5
C13—C12—C16122.0 (2)H23B—C23—H23C109.5
C11—C12—C16120.7 (2)C20—C21'—H21D109.5
C12—C13—C14124.4 (2)C20—C21'—H21E109.5
C12—C13—H13117.8H21D—C21'—H21E109.5
C14—C13—H13117.8C20—C21'—H21F109.5
C15—C14—C13116.8 (2)H21D—C21'—H21F109.5
C15—C14—C20121.5 (2)H21E—C21'—H21F109.5
C13—C14—C20121.7 (2)C20—C22'—H22D109.5
C14—C15—C10122.2 (2)C20—C22'—H22E109.5
C14—C15—H15118.9H22D—C22'—H22E109.5
C10—C15—H15118.9C20—C22'—H22F109.5
C18—C16—C17107.4 (2)H22D—C22'—H22F109.5
C18—C16—C19110.3 (2)H22E—C22'—H22F109.5
C17—C16—C19107.3 (3)C20—C23'—H23D109.5
C18—C16—C12110.3 (2)C20—C23'—H23E109.5
C17—C16—C12111.5 (2)H23D—C23'—H23E109.5
C19—C16—C12110.0 (2)C20—C23'—H23F109.5
C16—C17—H17A109.5H23D—C23'—H23F109.5
C16—C17—H17B109.5H23E—C23'—H23F109.5
H17A—C17—H17B109.5C3—N1—C2121.0 (3)
C16—C17—H17C109.5C3—N1—C1121.2 (3)
H17A—C17—H17C109.5C2—N1—C1117.8 (3)
H17B—C17—H17C109.5C9—N2—C6124.0 (2)
C16—C18—H18A109.5C11—O1—H1107 (3)
N1—C3—C4—C5179.6 (3)C9—C10—C15—C14176.1 (2)
C8—C3—C4—C51.0 (5)C13—C12—C16—C18119.7 (3)
C3—C4—C5—C60.1 (5)C11—C12—C16—C1861.4 (3)
C4—C5—C6—C71.3 (4)C13—C12—C16—C170.5 (4)
C4—C5—C6—N2177.6 (3)C11—C12—C16—C17179.4 (3)
C5—C6—C7—C81.4 (5)C13—C12—C16—C19118.4 (3)
N2—C6—C7—C8177.6 (3)C11—C12—C16—C1960.5 (3)
C6—C7—C8—C30.3 (5)C15—C14—C20—C22177.7 (3)
N1—C3—C8—C7179.7 (3)C13—C14—C20—C221.8 (4)
C4—C3—C8—C70.9 (5)C15—C14—C20—C2361.9 (4)
N2—C9—C10—C15175.4 (3)C13—C14—C20—C23118.6 (3)
N2—C9—C10—C111.4 (4)C15—C14—C20—C2156.2 (4)
C15—C10—C11—O1179.8 (2)C13—C14—C20—C21123.4 (3)
C9—C10—C11—O13.0 (4)C15—C14—C20—C21'1.0 (7)
C15—C10—C11—C120.8 (4)C13—C14—C20—C21'179.5 (6)
C9—C10—C11—C12176.0 (2)C15—C14—C20—C22'131.6 (6)
O1—C11—C12—C13179.5 (2)C13—C14—C20—C22'48.0 (7)
C10—C11—C12—C130.5 (4)C15—C14—C20—C23'118.5 (6)
O1—C11—C12—C160.5 (4)C13—C14—C20—C23'62.0 (7)
C10—C11—C12—C16178.5 (2)C8—C3—N1—C23.3 (5)
C11—C12—C13—C140.2 (4)C4—C3—N1—C2176.1 (3)
C16—C12—C13—C14178.8 (2)C8—C3—N1—C1179.7 (3)
C12—C13—C14—C150.1 (4)C4—C3—N1—C10.9 (5)
C12—C13—C14—C20179.4 (3)C10—C9—N2—C6175.0 (2)
C13—C14—C15—C100.4 (4)C7—C6—N2—C9156.2 (3)
C20—C14—C15—C10179.1 (3)C5—C6—N2—C922.8 (5)
C11—C10—C15—C140.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N20.83 (1)1.78 (2)2.544 (3)153 (4)
 

Acknowledgements

The authors acknowledge the SAIF, IIT, Madras for the data collection.

References

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