organic compounds
4,6-Di-tert-butyl-2-{(E)-[4-(dimethylamino)phenylimino]methyl}phenol
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
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.
Keywords: crystal structure; hydrogen bonding; Schiff base.
CCDC reference: 1507854
Structure description
et al., 2016; Khattab, 2005; Karthikeyan et al., 2006). We herein report the of title compound, which contains a C=N bond (Fig. 1).
have attracted much attention for their biological properties such as anti-bacterial, anti-cancer and antitumor (Ida MalarselviBond lengths in the title compound are comparable with those in a similar structure (Fun et al., 2013). 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 and Table 1). There are no significant intermolecular interactions beyond normal van der Waals contacts present in the crystal structure.
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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 . 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.
details are summarized in Table 2Structural data
CCDC reference: 1507854
https://doi.org/10.1107/S2414314617003960/vm4021sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617003960/vm4021Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617003960/vm4021Isup3.cml
Data collection: APEX2 (Bruker, 2004); cell
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).C23H32N2O | F(000) = 768 |
Mr = 352.50 | Dx = 1.102 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 22.8029 (15) Å | Cell parameters from 5165 reflections |
b = 9.9908 (7) Å | θ = 2.4–22.4° |
c = 9.3304 (6) Å | µ = 0.07 mm−1 |
β = 90.247 (2)° | T = 295 K |
V = 2125.6 (2) Å3 | Block, colourless |
Z = 4 | 0.34 × 0.28 × 0.24 mm |
Bruker Kappa APEXII CCD diffractometer | 2643 reflections with I > 2σ(I) |
ω and φ scan | Rint = 0.041 |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | θmax = 25.9°, θmin = 2.2° |
Tmin = 0.917, Tmax = 0.980 | h = −27→28 |
35692 measured reflections | k = −12→11 |
4143 independent reflections | l = −11→11 |
Refinement on F2 | 49 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.070 | H 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 reflections | Δρmax = 0.48 e Å−3 |
277 parameters | Δρmin = −0.40 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 1.08947 (15) | 0.2191 (4) | 0.4437 (5) | 0.1011 (13) | |
H1A | 1.058733 | 0.210591 | 0.373632 | 0.152* | |
H1B | 1.126262 | 0.195125 | 0.401163 | 0.152* | |
H1C | 1.091260 | 0.310001 | 0.476835 | 0.152* | |
C2 | 1.12567 (14) | 0.0568 (6) | 0.6207 (4) | 0.1144 (16) | |
H2A | 1.133763 | 0.086893 | 0.716527 | 0.172* | |
H2B | 1.159763 | 0.069731 | 0.562351 | 0.172* | |
H2C | 1.115647 | −0.036493 | 0.622452 | 0.172* | |
C3 | 1.02298 (11) | 0.1250 (3) | 0.6223 (3) | 0.0639 (8) | |
C4 | 0.97629 (11) | 0.2029 (3) | 0.5733 (3) | 0.0680 (8) | |
H4 | 0.982342 | 0.261991 | 0.497808 | 0.082* | |
C5 | 0.92141 (11) | 0.1945 (3) | 0.6339 (3) | 0.0636 (8) | |
H5 | 0.891252 | 0.248087 | 0.598714 | 0.076* | |
C6 | 0.91044 (10) | 0.1079 (3) | 0.7460 (3) | 0.0551 (7) | |
C7 | 0.95692 (12) | 0.0327 (4) | 0.7962 (3) | 0.0718 (9) | |
H7 | 0.950977 | −0.024917 | 0.873017 | 0.086* | |
C8 | 1.01151 (12) | 0.0404 (4) | 0.7364 (4) | 0.0760 (9) | |
H8 | 1.041600 | −0.012404 | 0.773195 | 0.091* | |
C9 | 0.80644 (11) | 0.1125 (3) | 0.7538 (3) | 0.0558 (7) | |
H9 | 0.805782 | 0.152980 | 0.664084 | 0.067* | |
C10 | 0.75150 (10) | 0.0801 (3) | 0.8222 (3) | 0.0506 (6) | |
C11 | 0.75054 (10) | 0.0212 (3) | 0.9600 (3) | 0.0513 (6) | |
C12 | 0.69728 (11) | −0.0174 (3) | 1.0215 (3) | 0.0495 (6) | |
C13 | 0.64680 (11) | 0.0056 (2) | 0.9426 (3) | 0.0498 (6) | |
H13 | 0.611210 | −0.019559 | 0.982777 | 0.060* | |
C14 | 0.64568 (10) | 0.0639 (3) | 0.8067 (3) | 0.0485 (6) | |
C15 | 0.69883 (11) | 0.1005 (3) | 0.7497 (3) | 0.0518 (6) | |
H15 | 0.699573 | 0.140223 | 0.659533 | 0.062* | |
C16 | 0.69585 (11) | −0.0847 (3) | 1.1696 (3) | 0.0571 (7) | |
C17 | 0.63306 (13) | −0.1193 (4) | 1.2142 (3) | 0.0757 (9) | |
H17A | 0.610419 | −0.038620 | 1.221550 | 0.114* | |
H17B | 0.633754 | −0.163897 | 1.305361 | 0.114* | |
H17C | 0.615673 | −0.177120 | 1.143687 | 0.114* | |
C18 | 0.72105 (13) | 0.0092 (3) | 1.2834 (3) | 0.0706 (8) | |
H18A | 0.697327 | 0.088351 | 1.288946 | 0.106* | |
H18B | 0.760412 | 0.033375 | 1.258066 | 0.106* | |
H18C | 0.721271 | −0.035210 | 1.374642 | 0.106* | |
C19 | 0.73069 (15) | −0.2162 (3) | 1.1661 (4) | 0.0806 (10) | |
H19A | 0.714146 | −0.274631 | 1.094936 | 0.121* | |
H19B | 0.728853 | −0.258575 | 1.258316 | 0.121* | |
H19C | 0.770836 | −0.197624 | 1.142814 | 0.121* | |
C20 | 0.58838 (12) | 0.0852 (3) | 0.7249 (3) | 0.0675 (7) | |
C21 | 0.5923 (2) | 0.0156 (6) | 0.5802 (5) | 0.0822 (9) | 0.716 (3) |
H21A | 0.597545 | −0.078832 | 0.594498 | 0.123* | 0.716 (3) |
H21B | 0.624950 | 0.050732 | 0.527729 | 0.123* | 0.716 (3) |
H21C | 0.556754 | 0.030864 | 0.527023 | 0.123* | 0.716 (3) |
C22 | 0.53550 (19) | 0.0335 (6) | 0.8033 (6) | 0.0861 (9) | 0.716 (3) |
H22A | 0.532518 | 0.077576 | 0.894448 | 0.129* | 0.716 (3) |
H22B | 0.539395 | −0.061207 | 0.817945 | 0.129* | 0.716 (3) |
H22C | 0.500839 | 0.051151 | 0.747706 | 0.129* | 0.716 (3) |
C23 | 0.5796 (2) | 0.2327 (5) | 0.6985 (6) | 0.0825 (8) | 0.716 (3) |
H23A | 0.543995 | 0.246161 | 0.645121 | 0.124* | 0.716 (3) |
H23B | 0.612123 | 0.267189 | 0.645041 | 0.124* | 0.716 (3) |
H23C | 0.577039 | 0.278641 | 0.788643 | 0.124* | 0.716 (3) |
C21' | 0.5948 (5) | 0.1512 (14) | 0.5788 (13) | 0.0814 (10) | 0.284 (3) |
H21D | 0.610243 | 0.239913 | 0.590714 | 0.122* | 0.284 (3) |
H21E | 0.557136 | 0.155938 | 0.532713 | 0.122* | 0.284 (3) |
H21F | 0.621063 | 0.099402 | 0.520875 | 0.122* | 0.284 (3) |
C22' | 0.5506 (5) | −0.0439 (14) | 0.7261 (14) | 0.0827 (10) | 0.284 (3) |
H22D | 0.568456 | −0.110274 | 0.666051 | 0.124* | 0.284 (3) |
H22E | 0.511993 | −0.023911 | 0.690690 | 0.124* | 0.284 (3) |
H22F | 0.547980 | −0.077336 | 0.822303 | 0.124* | 0.284 (3) |
C23' | 0.5480 (5) | 0.1814 (14) | 0.8104 (14) | 0.0835 (10) | 0.284 (3) |
H23D | 0.532563 | 0.135513 | 0.892300 | 0.125* | 0.284 (3) |
H23E | 0.516296 | 0.210602 | 0.750055 | 0.125* | 0.284 (3) |
H23F | 0.570293 | 0.257690 | 0.841582 | 0.125* | 0.284 (3) |
N1 | 1.07772 (10) | 0.1318 (4) | 0.5625 (3) | 0.0886 (9) | |
N2 | 0.85586 (9) | 0.0874 (2) | 0.8129 (2) | 0.0592 (6) | |
O1 | 0.80132 (8) | 0.0006 (2) | 1.0312 (2) | 0.0705 (6) | |
H1 | 0.8283 (12) | 0.023 (4) | 0.977 (3) | 0.106* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.074 (2) | 0.102 (3) | 0.127 (3) | −0.029 (2) | 0.037 (2) | −0.010 (3) |
C2 | 0.0412 (17) | 0.202 (5) | 0.100 (3) | 0.016 (2) | 0.0014 (17) | −0.016 (3) |
C3 | 0.0391 (14) | 0.083 (2) | 0.0700 (18) | −0.0094 (13) | 0.0000 (12) | −0.0063 (16) |
C4 | 0.0483 (16) | 0.073 (2) | 0.083 (2) | −0.0119 (14) | 0.0013 (14) | 0.0103 (16) |
C5 | 0.0416 (14) | 0.0618 (17) | 0.087 (2) | −0.0043 (12) | −0.0048 (13) | 0.0078 (15) |
C6 | 0.0401 (13) | 0.0642 (17) | 0.0610 (16) | −0.0062 (12) | −0.0004 (11) | 0.0003 (13) |
C7 | 0.0488 (16) | 0.096 (2) | 0.0704 (19) | 0.0013 (15) | −0.0033 (14) | 0.0174 (17) |
C8 | 0.0433 (16) | 0.101 (2) | 0.083 (2) | 0.0071 (16) | −0.0050 (14) | 0.0108 (19) |
C9 | 0.0453 (14) | 0.0645 (17) | 0.0576 (15) | −0.0033 (12) | 0.0020 (12) | 0.0026 (13) |
C10 | 0.0414 (13) | 0.0557 (15) | 0.0546 (15) | −0.0011 (11) | 0.0015 (11) | 0.0016 (12) |
C11 | 0.0398 (13) | 0.0596 (16) | 0.0545 (15) | 0.0038 (11) | −0.0031 (11) | 0.0009 (12) |
C12 | 0.0442 (13) | 0.0511 (14) | 0.0532 (14) | 0.0035 (11) | 0.0023 (11) | −0.0002 (11) |
C13 | 0.0409 (13) | 0.0522 (15) | 0.0564 (15) | −0.0003 (11) | 0.0036 (11) | −0.0003 (12) |
C14 | 0.0404 (13) | 0.0507 (14) | 0.0542 (14) | 0.0012 (11) | −0.0009 (10) | −0.0031 (12) |
C15 | 0.0468 (14) | 0.0579 (15) | 0.0509 (14) | 0.0004 (12) | −0.0007 (11) | 0.0049 (12) |
C16 | 0.0509 (15) | 0.0645 (17) | 0.0560 (15) | 0.0050 (12) | 0.0022 (12) | 0.0095 (13) |
C17 | 0.0686 (19) | 0.090 (2) | 0.0683 (19) | −0.0068 (17) | 0.0074 (15) | 0.0199 (17) |
C18 | 0.0682 (19) | 0.087 (2) | 0.0563 (16) | 0.0071 (16) | −0.0006 (14) | 0.0030 (16) |
C19 | 0.086 (2) | 0.071 (2) | 0.085 (2) | 0.0158 (17) | 0.0063 (18) | 0.0200 (17) |
C20 | 0.0441 (13) | 0.0855 (16) | 0.0729 (14) | 0.0065 (11) | −0.0171 (11) | −0.0013 (12) |
C21 | 0.0651 (17) | 0.1021 (19) | 0.0793 (16) | 0.0051 (16) | −0.0191 (14) | −0.0090 (15) |
C22 | 0.0555 (16) | 0.110 (2) | 0.0928 (19) | −0.0010 (15) | −0.0086 (14) | 0.0015 (17) |
C23 | 0.0651 (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) |
N1 | 0.0407 (13) | 0.133 (3) | 0.092 (2) | −0.0062 (15) | 0.0079 (13) | 0.0055 (19) |
N2 | 0.0405 (12) | 0.0713 (15) | 0.0658 (14) | −0.0034 (10) | 0.0007 (10) | 0.0042 (12) |
O1 | 0.0411 (10) | 0.1058 (17) | 0.0646 (13) | 0.0038 (10) | −0.0043 (9) | 0.0183 (11) |
C1—N1 | 1.437 (5) | C16—C19 | 1.536 (4) |
C1—H1A | 0.9600 | C17—H17A | 0.9600 |
C1—H1B | 0.9600 | C17—H17B | 0.9600 |
C1—H1C | 0.9600 | C17—H17C | 0.9600 |
C2—N1 | 1.431 (5) | C18—H18A | 0.9600 |
C2—H2A | 0.9600 | C18—H18B | 0.9600 |
C2—H2B | 0.9600 | C18—H18C | 0.9600 |
C2—H2C | 0.9600 | C19—H19A | 0.9600 |
C3—N1 | 1.371 (3) | C19—H19B | 0.9600 |
C3—C8 | 1.385 (4) | C19—H19C | 0.9600 |
C3—C4 | 1.394 (4) | C20—C22 | 1.505 (6) |
C4—C5 | 1.378 (4) | C20—C23 | 1.507 (6) |
C4—H4 | 0.9300 | C20—C21 | 1.522 (6) |
C5—C6 | 1.381 (4) | C20—C21' | 1.522 (12) |
C5—H5 | 0.9300 | C20—C22' | 1.551 (13) |
C6—C7 | 1.379 (4) | C20—C23' | 1.554 (12) |
C6—N2 | 1.410 (3) | C21—H21A | 0.9600 |
C7—C8 | 1.368 (4) | C21—H21B | 0.9600 |
C7—H7 | 0.9300 | C21—H21C | 0.9600 |
C8—H8 | 0.9300 | C22—H22A | 0.9600 |
C9—N2 | 1.277 (3) | C22—H22B | 0.9600 |
C9—C10 | 1.445 (3) | C22—H22C | 0.9600 |
C9—H9 | 0.9300 | C23—H23A | 0.9600 |
C10—C15 | 1.391 (3) | C23—H23B | 0.9600 |
C10—C11 | 1.414 (4) | C23—H23C | 0.9600 |
C11—O1 | 1.348 (3) | C21'—H21D | 0.9600 |
C11—C12 | 1.400 (3) | C21'—H21E | 0.9600 |
C12—C13 | 1.383 (3) | C21'—H21F | 0.9600 |
C12—C16 | 1.537 (4) | C22'—H22D | 0.9600 |
C13—C14 | 1.395 (4) | C22'—H22E | 0.9600 |
C13—H13 | 0.9300 | C22'—H22F | 0.9600 |
C14—C15 | 1.375 (3) | C23'—H23D | 0.9600 |
C14—C20 | 1.526 (3) | C23'—H23E | 0.9600 |
C15—H15 | 0.9300 | C23'—H23F | 0.9600 |
C16—C18 | 1.527 (4) | O1—H1 | 0.830 (10) |
C16—C17 | 1.532 (4) | ||
N1—C1—H1A | 109.5 | C16—C18—H18B | 109.5 |
N1—C1—H1B | 109.5 | H18A—C18—H18B | 109.5 |
H1A—C1—H1B | 109.5 | C16—C18—H18C | 109.5 |
N1—C1—H1C | 109.5 | H18A—C18—H18C | 109.5 |
H1A—C1—H1C | 109.5 | H18B—C18—H18C | 109.5 |
H1B—C1—H1C | 109.5 | C16—C19—H19A | 109.5 |
N1—C2—H2A | 109.5 | C16—C19—H19B | 109.5 |
N1—C2—H2B | 109.5 | H19A—C19—H19B | 109.5 |
H2A—C2—H2B | 109.5 | C16—C19—H19C | 109.5 |
N1—C2—H2C | 109.5 | H19A—C19—H19C | 109.5 |
H2A—C2—H2C | 109.5 | H19B—C19—H19C | 109.5 |
H2B—C2—H2C | 109.5 | C22—C20—C23 | 108.0 (3) |
N1—C3—C8 | 121.2 (3) | C22—C20—C21 | 109.0 (3) |
N1—C3—C4 | 122.3 (3) | C23—C20—C21 | 108.1 (4) |
C8—C3—C4 | 116.5 (2) | C22—C20—C14 | 113.3 (3) |
C5—C4—C3 | 121.7 (3) | C23—C20—C14 | 109.3 (3) |
C5—C4—H4 | 119.2 | C21—C20—C14 | 109.1 (3) |
C3—C4—H4 | 119.2 | C21'—C20—C14 | 115.0 (5) |
C4—C5—C6 | 121.1 (3) | C21'—C20—C22' | 115.0 (7) |
C4—C5—H5 | 119.5 | C14—C20—C22' | 110.8 (5) |
C6—C5—H5 | 119.5 | C21'—C20—C23' | 104.5 (7) |
C7—C6—C5 | 117.2 (2) | C14—C20—C23' | 109.7 (5) |
C7—C6—N2 | 116.7 (3) | C22'—C20—C23' | 100.4 (7) |
C5—C6—N2 | 126.1 (2) | C20—C21—H21A | 109.5 |
C8—C7—C6 | 122.0 (3) | C20—C21—H21B | 109.5 |
C8—C7—H7 | 119.0 | H21A—C21—H21B | 109.5 |
C6—C7—H7 | 119.0 | C20—C21—H21C | 109.5 |
C7—C8—C3 | 121.5 (3) | H21A—C21—H21C | 109.5 |
C7—C8—H8 | 119.3 | H21B—C21—H21C | 109.5 |
C3—C8—H8 | 119.3 | C20—C22—H22A | 109.5 |
N2—C9—C10 | 122.1 (3) | C20—C22—H22B | 109.5 |
N2—C9—H9 | 119.0 | H22A—C22—H22B | 109.5 |
C10—C9—H9 | 119.0 | C20—C22—H22C | 109.5 |
C15—C10—C11 | 119.1 (2) | H22A—C22—H22C | 109.5 |
C15—C10—C9 | 120.1 (2) | H22B—C22—H22C | 109.5 |
C11—C10—C9 | 120.8 (2) | C20—C23—H23A | 109.5 |
O1—C11—C12 | 120.0 (2) | C20—C23—H23B | 109.5 |
O1—C11—C10 | 119.7 (2) | H23A—C23—H23B | 109.5 |
C12—C11—C10 | 120.3 (2) | C20—C23—H23C | 109.5 |
C13—C12—C11 | 117.2 (2) | H23A—C23—H23C | 109.5 |
C13—C12—C16 | 122.0 (2) | H23B—C23—H23C | 109.5 |
C11—C12—C16 | 120.7 (2) | C20—C21'—H21D | 109.5 |
C12—C13—C14 | 124.4 (2) | C20—C21'—H21E | 109.5 |
C12—C13—H13 | 117.8 | H21D—C21'—H21E | 109.5 |
C14—C13—H13 | 117.8 | C20—C21'—H21F | 109.5 |
C15—C14—C13 | 116.8 (2) | H21D—C21'—H21F | 109.5 |
C15—C14—C20 | 121.5 (2) | H21E—C21'—H21F | 109.5 |
C13—C14—C20 | 121.7 (2) | C20—C22'—H22D | 109.5 |
C14—C15—C10 | 122.2 (2) | C20—C22'—H22E | 109.5 |
C14—C15—H15 | 118.9 | H22D—C22'—H22E | 109.5 |
C10—C15—H15 | 118.9 | C20—C22'—H22F | 109.5 |
C18—C16—C17 | 107.4 (2) | H22D—C22'—H22F | 109.5 |
C18—C16—C19 | 110.3 (2) | H22E—C22'—H22F | 109.5 |
C17—C16—C19 | 107.3 (3) | C20—C23'—H23D | 109.5 |
C18—C16—C12 | 110.3 (2) | C20—C23'—H23E | 109.5 |
C17—C16—C12 | 111.5 (2) | H23D—C23'—H23E | 109.5 |
C19—C16—C12 | 110.0 (2) | C20—C23'—H23F | 109.5 |
C16—C17—H17A | 109.5 | H23D—C23'—H23F | 109.5 |
C16—C17—H17B | 109.5 | H23E—C23'—H23F | 109.5 |
H17A—C17—H17B | 109.5 | C3—N1—C2 | 121.0 (3) |
C16—C17—H17C | 109.5 | C3—N1—C1 | 121.2 (3) |
H17A—C17—H17C | 109.5 | C2—N1—C1 | 117.8 (3) |
H17B—C17—H17C | 109.5 | C9—N2—C6 | 124.0 (2) |
C16—C18—H18A | 109.5 | C11—O1—H1 | 107 (3) |
N1—C3—C4—C5 | 179.6 (3) | C9—C10—C15—C14 | 176.1 (2) |
C8—C3—C4—C5 | −1.0 (5) | C13—C12—C16—C18 | −119.7 (3) |
C3—C4—C5—C6 | −0.1 (5) | C11—C12—C16—C18 | 61.4 (3) |
C4—C5—C6—C7 | 1.3 (4) | C13—C12—C16—C17 | −0.5 (4) |
C4—C5—C6—N2 | −177.6 (3) | C11—C12—C16—C17 | −179.4 (3) |
C5—C6—C7—C8 | −1.4 (5) | C13—C12—C16—C19 | 118.4 (3) |
N2—C6—C7—C8 | 177.6 (3) | C11—C12—C16—C19 | −60.5 (3) |
C6—C7—C8—C3 | 0.3 (5) | C15—C14—C20—C22 | 177.7 (3) |
N1—C3—C8—C7 | −179.7 (3) | C13—C14—C20—C22 | −1.8 (4) |
C4—C3—C8—C7 | 0.9 (5) | C15—C14—C20—C23 | −61.9 (4) |
N2—C9—C10—C15 | −175.4 (3) | C13—C14—C20—C23 | 118.6 (3) |
N2—C9—C10—C11 | 1.4 (4) | C15—C14—C20—C21 | 56.2 (4) |
C15—C10—C11—O1 | 179.8 (2) | C13—C14—C20—C21 | −123.4 (3) |
C9—C10—C11—O1 | 3.0 (4) | C15—C14—C20—C21' | −1.0 (7) |
C15—C10—C11—C12 | 0.8 (4) | C13—C14—C20—C21' | 179.5 (6) |
C9—C10—C11—C12 | −176.0 (2) | C15—C14—C20—C22' | 131.6 (6) |
O1—C11—C12—C13 | −179.5 (2) | C13—C14—C20—C22' | −48.0 (7) |
C10—C11—C12—C13 | −0.5 (4) | C15—C14—C20—C23' | −118.5 (6) |
O1—C11—C12—C16 | −0.5 (4) | C13—C14—C20—C23' | 62.0 (7) |
C10—C11—C12—C16 | 178.5 (2) | C8—C3—N1—C2 | −3.3 (5) |
C11—C12—C13—C14 | 0.2 (4) | C4—C3—N1—C2 | 176.1 (3) |
C16—C12—C13—C14 | −178.8 (2) | C8—C3—N1—C1 | 179.7 (3) |
C12—C13—C14—C15 | −0.1 (4) | C4—C3—N1—C1 | −0.9 (5) |
C12—C13—C14—C20 | 179.4 (3) | C10—C9—N2—C6 | 175.0 (2) |
C13—C14—C15—C10 | 0.4 (4) | C7—C6—N2—C9 | −156.2 (3) |
C20—C14—C15—C10 | −179.1 (3) | C5—C6—N2—C9 | 22.8 (5) |
C11—C10—C15—C14 | −0.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2 | 0.83 (1) | 1.78 (2) | 2.544 (3) | 153 (4) |
Acknowledgements
The authors acknowledge the SAIF, IIT, Madras for the data collection.
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