research communications
H-carbazol-3-yl)-10H-phenothiazine-3-carbaldehyde
of 10-ethyl-7-(9-ethyl-9aDepartment of Physics, S.D.N.B. Vaishnav College for Women, Chromepet, Chennai 600 044, India, and bIndustrial Chemistry Polymer Division, CSIR Central Leather Research Institute, Chennai 600 020, India
*Correspondence e-mail: lakssdnbvc@gmail.com
The title compound, C29H24N2OS, contains a phenothiazine moiety linked to a planar carbazole unit (r.m.s. deviation = 0.029 Å) by a C—C single bond. The phenothiazine moiety possesses a typical non-planar butterfly structure with a fold angle of 27.36 (9)° between the two benzene rings. The dihedral angle between the mean planes of the carbazole and phenothiazine units is 27.28 (5)°. In the crystal, molecules stack in pairs along the c-axis direction, linked by offset π–π interactions [intercentroid distance = 3.797 (1) Å]. There are C—H⋯π interactions present linking these dimers to form a three-dimensional structure.
Keywords: crystal structure; phenothiazine; carbazole; carbaldehyde; C—H⋯π interactions; π–π interactions.
CCDC reference: 1543611
1. Chemical context
Phenothiazine, related to the thiazine class of et al., 2011; Hagfeldt et al., 2010). One phenothiazine derivative (MCDP) is used to measure the activity of monoamine oxidase in blood (Fujii et al., 1993). They are also used as neuroleptics, sedatives, analgesics, anti-emetics and antihistamines (Harris & Klein, 1987). Triflupromazine phenothiazine hydrochloride is one of the most potent tranquilizer drug molecules (Phelps & Cordes, 1974). The phenothiazine derivative thiethylperazine has the properties of an anti-emetic and is widely used for the control of post-operative vomiting, in radiation therapy and vomiting associated with malignant disease (McDowell, 1970, 1978). N-Alkylamino carbazoles show significant anti-convulsant and diuretic activity (Shoeb et al., 1973). One of them, rimcazole, is a well known anti-pyretic and neuroleptic agent (Ferris et al., 1986). In view of this interest, we have synthesized the title phenothiazine derivative and report herein on its crystal structure.
is very important as it occurs in various antipsychotic drugs. Phenothiazine derivatives have been used in dye-sensitized solar cells to study the effect of conjugated linkers on device performance (Kim2. Structural commentary
In the title compound, the phenothiazine moiety has a non-planar butterfly structure (Fig. 1), similar to that observed for 10-methyl-10H-phenothiazine (Malikireddy et al., 2016). The central six-membered ring (N2/C18/C19/S1/C28/C23) adopts a boat conformation [puckering parameters are: QT = 0.4567 (16) Å, θ = 102.8 (2)°, φ = 182.8 (2)°]. The fold angle of 27.36 (9)° between the two benzene rings of this moiety compares well with the values reported for similar compounds (CSD; Groom et al., 2016). The dihedral angle between the planes of the two benzene rings of the carbazole ring is 2.94 (10)° and the dihedral angle between the mean planes of the carbazole and phenothiazine ring systems is 27.28 (5)°. The aldehyde group is almost coplanar with the benzene ring to which it is attached, the C27—C26—C29—O1 torsion angle being 0.9 (4)°. The ethyl groups protrude out of the planes of the carbazole and phenothiazine skeletons, as indicated by the torsion angles C6—N1—C7—C8 = 87.7 (3)° and C23—N2—C21—C22 = −83.2 (2)°.
3. Supramolecular features
In the crystal, inversion-related molecules stack in pairs along the c-axis direction, linked by offset π–π interactions [Cg5⋯Cg5i = 3.7965 (11) Å, interplanar distance = 3.5133 (8) Å, slippage = 1.439 Å, Cg5 is the centroid of the C15–C20 ring; symmetry code: (i) −x + 1, −y, −z + 2]. There are also C–H⋯π interactions present linking these dimers to form a three-dimensional structure (Table 1 and Fig. 2).
4. Database survey
A search of the Cambridge Structural Database (CSD, Version 5.38, update February 2017; Groom et al., 2016) for compounds containing either a phenothiazine, carbazole or carbaldehyde unit gave 433 hits for compounds containing a phenothiazine unit, and 2293 hits for compounds containing a carbazole unit. Out of these entries, six compounds were found to possess both phenothiazine and carbazole ring systems, and one compound contains all three units, phenothiazine, carbazole and a carbaldehyde unit, but with the carbazole unit linked directly to the N atom of the phenothiazine unit, viz. 10-(9-hexyl-9H-carbazol-3yl)-10H-phenothiazine-3-carbaldehyde (IWABUF; Karuppasamy et al., 2017).
5. Synthesis and crystallization
To a mixture of 7-bromo-10-ethyl-10H-phenothiazine-3-carbaldehyde (3 g, 0.0089 mol), 9-ethyl-9H-carbazole-3-boronic acid pinnacol ester (3.17 g, 1.1 eq.), Pd(PPh3)4 (518 mg, 5% mol) and K2CO3 (2.48 g, 2 eq.) under high vacuum was added a mixture of toluene:water (2:1). The resulting mixture was heated to reflux under an N2 atmosphere for ca 24 h. On completion of the reaction (monitored by TLC), it was quenched by addition of saturated double-distilled H2O and extracted with dichloromethane. The organic phases were collected and washed with brine and dried over anhydrous Na2SO4 and then concentrated. The product was purified by on silica gel using ethyl acetate:n-hexane (12:88, v/v) as to give the title compound as a pale-yellow crystalline solid (yield 80%). It was characterized by 1H NMR, 13C NMR, IR and ESI–MASS. Brown block-like crystals of the title compound were obtained by slow evaporation at room temperature of a solution in dichloromethane and acetonitrile (1:1 v/v).
6. Refinement
Crystal data, data collection and structure . All H atoms were placed in calculated positions and refined using a riding-model approximation: C—H = 0.93–0.98 Å with Uiso(H) = 1.5Ueq(C-methyl) and 1.2Ueq(C) for other H atoms.
details are summarized in Table 2Supporting information
CCDC reference: 1543611
https://doi.org/10.1107/S2056989017005540/su5357sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017005540/su5357Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989017005540/su5357Isup3.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: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).C29H24N2OS | F(000) = 944 |
Mr = 448.56 | Dx = 1.316 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 9.4677 (6) Å | Cell parameters from 6254 reflections |
b = 25.7169 (13) Å | θ = 2.4–23.8° |
c = 9.5704 (5) Å | µ = 0.17 mm−1 |
β = 103.681 (2)° | T = 296 K |
V = 2264.1 (2) Å3 | Block, brown |
Z = 4 | 0.30 × 0.25 × 0.20 mm |
Bruker Kappa APEXII CCD diffractometer | 2974 reflections with I > 2σ(I) |
Bruker axs kappa axes2 CCD scans | Rint = 0.036 |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | θmax = 25.0°, θmin = 2.3° |
Tmin = 0.677, Tmax = 0.745 | h = −11→9 |
25526 measured reflections | k = −30→30 |
3981 independent reflections | l = −11→11 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0455P)2 + 0.8313P] where P = (Fo2 + 2Fc2)/3 |
3981 reflections | (Δ/σ)max = 0.004 |
300 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.20 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 | ||
S1 | 0.49912 (6) | 0.15680 (2) | 0.93196 (6) | 0.04721 (18) | |
N2 | 0.78333 (17) | 0.11025 (6) | 1.10224 (16) | 0.0385 (4) | |
C5 | 0.3217 (2) | −0.16204 (8) | 0.5560 (2) | 0.0395 (5) | |
C15 | 0.5175 (2) | 0.01031 (7) | 0.7928 (2) | 0.0385 (5) | |
C12 | 0.4282 (2) | −0.02290 (8) | 0.6785 (2) | 0.0393 (5) | |
C10 | 0.3469 (2) | −0.10671 (8) | 0.5781 (2) | 0.0380 (5) | |
C17 | 0.7263 (2) | 0.02401 (8) | 0.9923 (2) | 0.0423 (5) | |
H17 | 0.8081 | 0.0101 | 1.0547 | 0.051* | |
C18 | 0.6941 (2) | 0.07646 (7) | 1.0030 (2) | 0.0362 (5) | |
C23 | 0.7869 (2) | 0.16369 (7) | 1.0771 (2) | 0.0374 (5) | |
C21 | 0.9010 (2) | 0.08767 (8) | 1.2138 (2) | 0.0443 (5) | |
H21A | 0.8654 | 0.0561 | 1.2489 | 0.053* | |
H21B | 0.9253 | 0.1119 | 1.2936 | 0.053* | |
C28 | 0.6646 (2) | 0.18995 (7) | 0.9936 (2) | 0.0381 (5) | |
C16 | 0.6397 (2) | −0.00788 (8) | 0.8909 (2) | 0.0424 (5) | |
H16 | 0.6642 | −0.0428 | 0.8884 | 0.051* | |
N1 | 0.1914 (2) | −0.11924 (7) | 0.35912 (18) | 0.0470 (5) | |
C11 | 0.4296 (2) | −0.07678 (8) | 0.6882 (2) | 0.0394 (5) | |
H11 | 0.4864 | −0.0929 | 0.7692 | 0.047* | |
C26 | 0.7923 (2) | 0.27184 (8) | 1.0287 (2) | 0.0438 (5) | |
C27 | 0.6683 (2) | 0.24282 (8) | 0.9705 (2) | 0.0436 (5) | |
H27 | 0.5866 | 0.2593 | 0.9152 | 0.052* | |
C9 | 0.2620 (2) | −0.08213 (8) | 0.4554 (2) | 0.0420 (5) | |
C19 | 0.5669 (2) | 0.09442 (7) | 0.9097 (2) | 0.0377 (5) | |
C20 | 0.4834 (2) | 0.06242 (7) | 0.8066 (2) | 0.0403 (5) | |
H20 | 0.4014 | 0.0762 | 0.7442 | 0.048* | |
C14 | 0.2576 (2) | −0.02860 (8) | 0.4439 (2) | 0.0498 (6) | |
H14 | 0.1999 | −0.0124 | 0.3635 | 0.060* | |
O1 | 0.7031 (2) | 0.35389 (7) | 0.9339 (2) | 0.0900 (7) | |
C13 | 0.3407 (2) | 0.00008 (8) | 0.5540 (2) | 0.0482 (5) | |
H13 | 0.3392 | 0.0361 | 0.5463 | 0.058* | |
C24 | 0.9103 (2) | 0.19363 (8) | 1.1355 (2) | 0.0444 (5) | |
H24 | 0.9926 | 0.1776 | 1.1913 | 0.053* | |
C6 | 0.2262 (2) | −0.16776 (8) | 0.4193 (2) | 0.0420 (5) | |
C29 | 0.8000 (3) | 0.32760 (9) | 1.0036 (3) | 0.0579 (6) | |
H29 | 0.8870 | 0.3443 | 1.0448 | 0.069* | |
C4 | 0.3684 (2) | −0.20599 (8) | 0.6386 (2) | 0.0474 (5) | |
H4 | 0.4303 | −0.2030 | 0.7295 | 0.057* | |
C7 | 0.0799 (2) | −0.10852 (9) | 0.2300 (2) | 0.0535 (6) | |
H7A | 0.0743 | −0.1375 | 0.1641 | 0.064* | |
H7B | 0.1074 | −0.0779 | 0.1836 | 0.064* | |
C25 | 0.9118 (2) | 0.24642 (8) | 1.1116 (2) | 0.0474 (5) | |
H25 | 0.9951 | 0.2654 | 1.1521 | 0.057* | |
C1 | 0.1828 (2) | −0.21668 (8) | 0.3631 (2) | 0.0509 (6) | |
H1 | 0.1226 | −0.2204 | 0.2716 | 0.061* | |
C22 | 1.0392 (2) | 0.07482 (9) | 1.1657 (2) | 0.0561 (6) | |
H22A | 1.0222 | 0.0452 | 1.1028 | 0.084* | |
H22B | 1.1159 | 0.0671 | 1.2483 | 0.084* | |
H22C | 1.0665 | 0.1041 | 1.1156 | 0.084* | |
C3 | 0.3213 (3) | −0.25401 (9) | 0.5835 (3) | 0.0553 (6) | |
H3 | 0.3502 | −0.2836 | 0.6389 | 0.066* | |
C2 | 0.2315 (2) | −0.25924 (9) | 0.4470 (3) | 0.0560 (6) | |
H2 | 0.2037 | −0.2923 | 0.4116 | 0.067* | |
C8 | −0.0676 (3) | −0.09976 (12) | 0.2586 (3) | 0.0787 (8) | |
H8A | −0.0938 | −0.1292 | 0.3088 | 0.118* | |
H8B | −0.1380 | −0.0954 | 0.1690 | 0.118* | |
H8C | −0.0654 | −0.0691 | 0.3163 | 0.118* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0356 (3) | 0.0397 (3) | 0.0623 (4) | 0.0083 (2) | 0.0034 (3) | −0.0034 (3) |
N2 | 0.0359 (10) | 0.0368 (9) | 0.0398 (9) | 0.0067 (7) | 0.0032 (8) | 0.0026 (7) |
C5 | 0.0376 (12) | 0.0409 (11) | 0.0417 (11) | 0.0010 (9) | 0.0125 (9) | 0.0006 (9) |
C15 | 0.0387 (12) | 0.0376 (11) | 0.0420 (11) | 0.0009 (9) | 0.0150 (9) | 0.0031 (9) |
C12 | 0.0394 (12) | 0.0407 (11) | 0.0399 (11) | 0.0002 (9) | 0.0133 (9) | 0.0028 (9) |
C10 | 0.0378 (11) | 0.0404 (11) | 0.0376 (11) | 0.0033 (9) | 0.0123 (9) | 0.0023 (9) |
C17 | 0.0382 (12) | 0.0389 (11) | 0.0473 (12) | 0.0075 (9) | 0.0052 (10) | 0.0064 (9) |
C18 | 0.0345 (11) | 0.0367 (11) | 0.0388 (11) | 0.0034 (9) | 0.0114 (9) | 0.0044 (9) |
C23 | 0.0377 (11) | 0.0403 (11) | 0.0346 (10) | 0.0066 (9) | 0.0093 (9) | −0.0006 (9) |
C21 | 0.0448 (13) | 0.0438 (12) | 0.0404 (11) | 0.0086 (10) | 0.0023 (10) | 0.0043 (9) |
C28 | 0.0386 (12) | 0.0393 (11) | 0.0358 (11) | 0.0042 (9) | 0.0072 (9) | −0.0033 (9) |
C16 | 0.0438 (13) | 0.0337 (11) | 0.0503 (12) | 0.0038 (9) | 0.0124 (10) | 0.0026 (9) |
N1 | 0.0502 (11) | 0.0465 (10) | 0.0401 (9) | −0.0018 (8) | 0.0023 (8) | 0.0029 (8) |
C11 | 0.0397 (12) | 0.0425 (12) | 0.0362 (11) | 0.0041 (9) | 0.0094 (9) | 0.0048 (9) |
C26 | 0.0512 (13) | 0.0419 (12) | 0.0379 (11) | 0.0036 (10) | 0.0096 (10) | −0.0023 (9) |
C27 | 0.0469 (13) | 0.0407 (12) | 0.0394 (11) | 0.0081 (10) | 0.0026 (10) | 0.0002 (9) |
C9 | 0.0457 (13) | 0.0424 (12) | 0.0380 (11) | −0.0021 (10) | 0.0103 (10) | 0.0034 (9) |
C19 | 0.0353 (11) | 0.0365 (11) | 0.0418 (11) | 0.0047 (9) | 0.0104 (9) | 0.0034 (9) |
C20 | 0.0348 (11) | 0.0417 (12) | 0.0429 (11) | 0.0041 (9) | 0.0060 (9) | 0.0051 (9) |
C14 | 0.0568 (14) | 0.0477 (13) | 0.0408 (12) | 0.0019 (11) | 0.0032 (11) | 0.0104 (10) |
O1 | 0.0925 (15) | 0.0504 (11) | 0.1099 (16) | 0.0041 (10) | −0.0101 (13) | 0.0203 (11) |
C13 | 0.0585 (15) | 0.0379 (11) | 0.0474 (12) | 0.0016 (10) | 0.0109 (11) | 0.0065 (10) |
C24 | 0.0384 (12) | 0.0436 (12) | 0.0476 (12) | 0.0065 (10) | 0.0034 (10) | −0.0025 (10) |
C6 | 0.0371 (12) | 0.0443 (12) | 0.0453 (12) | −0.0021 (9) | 0.0112 (9) | 0.0009 (10) |
C29 | 0.0669 (17) | 0.0443 (13) | 0.0594 (15) | −0.0015 (12) | 0.0087 (13) | 0.0006 (12) |
C4 | 0.0461 (13) | 0.0454 (13) | 0.0497 (12) | 0.0033 (10) | 0.0095 (10) | 0.0051 (10) |
C7 | 0.0557 (15) | 0.0612 (14) | 0.0395 (12) | −0.0032 (11) | 0.0035 (11) | 0.0043 (11) |
C25 | 0.0450 (13) | 0.0477 (12) | 0.0479 (12) | −0.0027 (10) | 0.0076 (10) | −0.0064 (10) |
C1 | 0.0441 (13) | 0.0527 (14) | 0.0539 (13) | −0.0096 (11) | 0.0074 (11) | −0.0053 (11) |
C22 | 0.0432 (13) | 0.0576 (14) | 0.0610 (15) | 0.0145 (11) | −0.0006 (11) | −0.0043 (12) |
C3 | 0.0539 (15) | 0.0431 (13) | 0.0692 (16) | −0.0002 (11) | 0.0152 (13) | 0.0084 (11) |
C2 | 0.0500 (14) | 0.0444 (13) | 0.0740 (17) | −0.0101 (11) | 0.0154 (13) | −0.0058 (12) |
C8 | 0.0529 (17) | 0.099 (2) | 0.0816 (19) | 0.0087 (15) | 0.0108 (14) | 0.0031 (17) |
S1—C28 | 1.759 (2) | C26—C27 | 1.392 (3) |
S1—C19 | 1.7595 (19) | C26—C29 | 1.459 (3) |
N2—C23 | 1.397 (2) | C27—H27 | 0.9300 |
N2—C18 | 1.412 (2) | C9—C14 | 1.381 (3) |
N2—C21 | 1.468 (2) | C19—C20 | 1.381 (3) |
C5—C4 | 1.390 (3) | C20—H20 | 0.9300 |
C5—C6 | 1.411 (3) | C14—C13 | 1.372 (3) |
C5—C10 | 1.450 (3) | C14—H14 | 0.9300 |
C15—C16 | 1.387 (3) | O1—C29 | 1.206 (3) |
C15—C20 | 1.392 (3) | C13—H13 | 0.9300 |
C15—C12 | 1.485 (3) | C24—C25 | 1.377 (3) |
C12—C11 | 1.388 (3) | C24—H24 | 0.9300 |
C12—C13 | 1.410 (3) | C6—C1 | 1.392 (3) |
C10—C11 | 1.388 (3) | C29—H29 | 0.9300 |
C10—C9 | 1.406 (3) | C4—C3 | 1.375 (3) |
C17—C16 | 1.382 (3) | C4—H4 | 0.9300 |
C17—C18 | 1.392 (3) | C7—C8 | 1.502 (3) |
C17—H17 | 0.9300 | C7—H7A | 0.9700 |
C18—C19 | 1.397 (3) | C7—H7B | 0.9700 |
C23—C24 | 1.400 (3) | C25—H25 | 0.9300 |
C23—C28 | 1.413 (3) | C1—C2 | 1.371 (3) |
C21—C22 | 1.522 (3) | C1—H1 | 0.9300 |
C21—H21A | 0.9700 | C22—H22A | 0.9600 |
C21—H21B | 0.9700 | C22—H22B | 0.9600 |
C28—C27 | 1.379 (3) | C22—H22C | 0.9600 |
C16—H16 | 0.9300 | C3—C2 | 1.386 (3) |
N1—C6 | 1.381 (3) | C3—H3 | 0.9300 |
N1—C9 | 1.384 (3) | C2—H2 | 0.9300 |
N1—C7 | 1.449 (3) | C8—H8A | 0.9600 |
C11—H11 | 0.9300 | C8—H8B | 0.9600 |
C26—C25 | 1.383 (3) | C8—H8C | 0.9600 |
C28—S1—C19 | 99.26 (9) | C20—C19—S1 | 117.78 (14) |
C23—N2—C18 | 121.66 (15) | C18—C19—S1 | 120.54 (15) |
C23—N2—C21 | 117.98 (16) | C19—C20—C15 | 122.33 (18) |
C18—N2—C21 | 118.46 (15) | C19—C20—H20 | 118.8 |
C4—C5—C6 | 119.35 (19) | C15—C20—H20 | 118.8 |
C4—C5—C10 | 134.10 (19) | C13—C14—C9 | 118.27 (19) |
C6—C5—C10 | 106.54 (17) | C13—C14—H14 | 120.9 |
C16—C15—C20 | 115.82 (18) | C9—C14—H14 | 120.9 |
C16—C15—C12 | 122.90 (18) | C14—C13—C12 | 122.65 (19) |
C20—C15—C12 | 121.28 (18) | C14—C13—H13 | 118.7 |
C11—C12—C13 | 117.99 (18) | C12—C13—H13 | 118.7 |
C11—C12—C15 | 122.01 (17) | C25—C24—C23 | 121.09 (19) |
C13—C12—C15 | 119.99 (18) | C25—C24—H24 | 119.5 |
C11—C10—C9 | 119.55 (18) | C23—C24—H24 | 119.5 |
C11—C10—C5 | 134.33 (18) | N1—C6—C1 | 129.5 (2) |
C9—C10—C5 | 106.12 (17) | N1—C6—C5 | 109.26 (17) |
C16—C17—C18 | 121.50 (18) | C1—C6—C5 | 121.24 (19) |
C16—C17—H17 | 119.3 | O1—C29—C26 | 125.5 (2) |
C18—C17—H17 | 119.3 | O1—C29—H29 | 117.2 |
C17—C18—C19 | 116.38 (18) | C26—C29—H29 | 117.2 |
C17—C18—N2 | 122.63 (17) | C3—C4—C5 | 118.8 (2) |
C19—C18—N2 | 120.99 (17) | C3—C4—H4 | 120.6 |
N2—C23—C24 | 121.61 (17) | C5—C4—H4 | 120.6 |
N2—C23—C28 | 121.17 (18) | N1—C7—C8 | 113.25 (19) |
C24—C23—C28 | 117.21 (18) | N1—C7—H7A | 108.9 |
N2—C21—C22 | 115.14 (17) | C8—C7—H7A | 108.9 |
N2—C21—H21A | 108.5 | N1—C7—H7B | 108.9 |
C22—C21—H21A | 108.5 | C8—C7—H7B | 108.9 |
N2—C21—H21B | 108.5 | H7A—C7—H7B | 107.7 |
C22—C21—H21B | 108.5 | C24—C25—C26 | 121.5 (2) |
H21A—C21—H21B | 107.5 | C24—C25—H25 | 119.3 |
C27—C28—C23 | 120.91 (19) | C26—C25—H25 | 119.3 |
C27—C28—S1 | 118.57 (15) | C2—C1—C6 | 117.9 (2) |
C23—C28—S1 | 120.23 (15) | C2—C1—H1 | 121.1 |
C17—C16—C15 | 122.44 (18) | C6—C1—H1 | 121.1 |
C17—C16—H16 | 118.8 | C21—C22—H22A | 109.5 |
C15—C16—H16 | 118.8 | C21—C22—H22B | 109.5 |
C6—N1—C9 | 108.37 (16) | H22A—C22—H22B | 109.5 |
C6—N1—C7 | 125.54 (18) | C21—C22—H22C | 109.5 |
C9—N1—C7 | 125.18 (18) | H22A—C22—H22C | 109.5 |
C12—C11—C10 | 120.52 (18) | H22B—C22—H22C | 109.5 |
C12—C11—H11 | 119.7 | C4—C3—C2 | 121.3 (2) |
C10—C11—H11 | 119.7 | C4—C3—H3 | 119.4 |
C25—C26—C27 | 118.33 (19) | C2—C3—H3 | 119.4 |
C25—C26—C29 | 119.6 (2) | C1—C2—C3 | 121.4 (2) |
C27—C26—C29 | 122.1 (2) | C1—C2—H2 | 119.3 |
C28—C27—C26 | 121.00 (19) | C3—C2—H2 | 119.3 |
C28—C27—H27 | 119.5 | C7—C8—H8A | 109.5 |
C26—C27—H27 | 119.5 | C7—C8—H8B | 109.5 |
C14—C9—N1 | 129.31 (18) | H8A—C8—H8B | 109.5 |
C14—C9—C10 | 121.02 (19) | C7—C8—H8C | 109.5 |
N1—C9—C10 | 109.67 (17) | H8A—C8—H8C | 109.5 |
C20—C19—C18 | 121.40 (18) | H8B—C8—H8C | 109.5 |
C16—C15—C12—C11 | 21.4 (3) | C5—C10—C9—C14 | 178.0 (2) |
C20—C15—C12—C11 | −159.25 (19) | C11—C10—C9—N1 | 178.85 (18) |
C16—C15—C12—C13 | −157.3 (2) | C5—C10—C9—N1 | −2.0 (2) |
C20—C15—C12—C13 | 22.1 (3) | C17—C18—C19—C20 | −4.0 (3) |
C4—C5—C10—C11 | 1.8 (4) | N2—C18—C19—C20 | 176.20 (18) |
C6—C5—C10—C11 | −179.4 (2) | C17—C18—C19—S1 | 169.74 (15) |
C4—C5—C10—C9 | −177.1 (2) | N2—C18—C19—S1 | −10.1 (3) |
C6—C5—C10—C9 | 1.7 (2) | C28—S1—C19—C20 | −151.56 (16) |
C16—C17—C18—C19 | 2.3 (3) | C28—S1—C19—C18 | 34.50 (18) |
C16—C17—C18—N2 | −177.84 (18) | C18—C19—C20—C15 | 2.3 (3) |
C23—N2—C18—C17 | 153.75 (19) | S1—C19—C20—C15 | −171.57 (16) |
C21—N2—C18—C17 | −10.2 (3) | C16—C15—C20—C19 | 1.1 (3) |
C23—N2—C18—C19 | −26.4 (3) | C12—C15—C20—C19 | −178.31 (19) |
C21—N2—C18—C19 | 169.58 (18) | N1—C9—C14—C13 | −178.6 (2) |
C18—N2—C23—C24 | −152.34 (19) | C10—C9—C14—C13 | 1.3 (3) |
C21—N2—C23—C24 | 11.7 (3) | C9—C14—C13—C12 | −0.9 (3) |
C18—N2—C23—C28 | 28.8 (3) | C11—C12—C13—C14 | 0.2 (3) |
C21—N2—C23—C28 | −167.15 (17) | C15—C12—C13—C14 | 178.9 (2) |
C23—N2—C21—C22 | −83.2 (2) | N2—C23—C24—C25 | −179.10 (19) |
C18—N2—C21—C22 | 81.4 (2) | C28—C23—C24—C25 | −0.2 (3) |
N2—C23—C28—C27 | 179.27 (18) | C9—N1—C6—C1 | −179.4 (2) |
C24—C23—C28—C27 | 0.4 (3) | C7—N1—C6—C1 | 11.1 (4) |
N2—C23—C28—S1 | 5.6 (3) | C9—N1—C6—C5 | −0.6 (2) |
C24—C23—C28—S1 | −173.33 (15) | C7—N1—C6—C5 | −170.09 (19) |
C19—S1—C28—C27 | 153.97 (16) | C4—C5—C6—N1 | 178.28 (19) |
C19—S1—C28—C23 | −32.19 (17) | C10—C5—C6—N1 | −0.7 (2) |
C18—C17—C16—C15 | 1.1 (3) | C4—C5—C6—C1 | −2.8 (3) |
C20—C15—C16—C17 | −2.8 (3) | C10—C5—C6—C1 | 178.24 (19) |
C12—C15—C16—C17 | 176.64 (19) | C25—C26—C29—O1 | −179.7 (2) |
C13—C12—C11—C10 | 0.0 (3) | C27—C26—C29—O1 | 0.9 (4) |
C15—C12—C11—C10 | −178.71 (18) | C6—C5—C4—C3 | 0.8 (3) |
C9—C10—C11—C12 | 0.4 (3) | C10—C5—C4—C3 | 179.5 (2) |
C5—C10—C11—C12 | −178.4 (2) | C6—N1—C7—C8 | 87.7 (3) |
C23—C28—C27—C26 | 0.0 (3) | C9—N1—C7—C8 | −80.1 (3) |
S1—C28—C27—C26 | 173.83 (16) | C23—C24—C25—C26 | −0.4 (3) |
C25—C26—C27—C28 | −0.6 (3) | C27—C26—C25—C24 | 0.8 (3) |
C29—C26—C27—C28 | 178.8 (2) | C29—C26—C25—C24 | −178.6 (2) |
C6—N1—C9—C14 | −178.4 (2) | N1—C6—C1—C2 | −178.9 (2) |
C7—N1—C9—C14 | −8.8 (4) | C5—C6—C1—C2 | 2.4 (3) |
C6—N1—C9—C10 | 1.7 (2) | C5—C4—C3—C2 | 1.4 (3) |
C7—N1—C9—C10 | 171.23 (19) | C6—C1—C2—C3 | −0.1 (3) |
C11—C10—C9—C14 | −1.1 (3) | C4—C3—C2—C1 | −1.9 (4) |
Cg3 and Cg4 are the centroids of the C1–C6 and C9–C14 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H21A···Cg4i | 0.97 | 2.95 | 3.596 (2) | 125 |
C25—H25···Cg3ii | 0.93 | 2.96 | 3.558 (2) | 123 |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+3/2, y+1/2, −z+3/2. |
Acknowledgements
The authors thank the single-crystal XRD facility, SAIF IIT Madras, Chennai, for the data collection.
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