organic compounds
Methyl (6R*,6aR*,12bR*)-2,4-dimethyl-6-(2-methylphenyl)-1,3-dioxo-2,3,4,6a,7,12b-hexahydro-1H,6H-chromeno[4′,3′:4,5]pyrano[2,3-d]pyrimidine-6a-carboxylate
aDepartment of Physics, Bhaktavatsalam Memorial College for women, Koratur, Chennai 600 080, Tamilnadu, India, bPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India, cDepartment of Organic Chemistry, University of Madras, Maraimalai campus,Chennai-600 025, India, and dDepartment of Physics, Sree Abiraami College of Arts and Science, Gudiyattum,Vellore 635 803, Tamilnadu, India
*Correspondence e-mail: guqmc@yahoo.com
In the title compound, C24H24N2O6, the mean planes of the pyran rings (A and B) are inclined to one another by 69.2 (1)°, while the aromatic ring (D) of the chromene ring system makes dihedral angles of 63.42 (11) and 66.81 (12)° with the pyrimidine (C) and benzene (E) rings, respectively. Pyran ring A has an half-chair conformation, while pyran ring B has an with the spiro C atom as the flap. In the crystal, molecules are linked by C—H⋯O hydrogen bonds, forming a supramolecular three-dimensional network. There are also a number of C—H⋯π interactions present.
Keywords: crystal structure; chromene; pyrimidine; pyran; C—H⋯O hydrogen bonds; C—H⋯π interactions.
CCDC reference: 938663
Structure description
Chromenes are used in the fields of medicine, cosmetics and as fluorescent dyes. 2-Oxo-2H-chromenes are efficient fluorophores characterized by good emission quantum yields and are used as materials for lasers in organic light-emitting devices, non-linear optical chromeophores and fluorescent labels (Sreenivasa et al., 2013). They exhibit anticancer, anti-Alzheimer's and anti-Parkinson's activity and are used to treat Huntington's disease (Andrani & Lapi, 1960; Zhang et al., 1982). They also exhibit antiviral, antifungal, anti-inflammatory and antidiabetic activity (Kemnitzer et al., 2008; Sui Xiong et al., 2006; Tang et al., 2007), and antimicrobial activity (Sangani et al., 2012).
The molecular structure of the title compound is illustrated in Fig. 1. The compound crystallizes as a racemate with of R,R,R at atoms C11(position 6), C12(position 6a) and C6(position 12b), respectively (see Scheme). The bond distances and bond angles are in good agreement with the values reported for similar structures (Swaminathan et al., 2015; Ponnusamy et al., 2013). The sp2 of atoms N1 and N2 are indicated by the sum of the bond angles of 359.8 and 360.0°, respectively. Pyran ring A has an half-chair conformation [puckering parameters: amplitude (Q) = 0.531 (2) Å, θ = 52.3 (2)°, φ = 273.2 (3)°], while pyran ring B has an with atom C12 as the flap [puckering parameters: amplitude (Q) = 0.493 (2) Å, θ = 128.0 (2)°, φ = 289.5 (3)°]. The mean planes of the pyran rings (A and B) are inclined to one another by 69.2 (1)°, while the aromatic ring (D) of the chromene ring system makes dihedral angles of 63.42 (11) and 66.81 (12)° with the pyrimidine (C) and benzene (E) rings, respectively. The methyl and carbonyl groups attached to the different ring systems of the molecule tend to be coplanar with the respective rings, other than atoms O1 and C25 which deviate by 0.210 (1) and 0.123 (3) Å, respectively, from the pyrimidene ring mean plane.
In the crystal, molecules are linked by C—H⋯O hydrogen bonds, forming a supramolecular three-dimensional network (Table 1 and Fig. 2). There are also a number of C—H⋯π interactions present (Table 1).
Synthesis and crystallization
The title compound was synthesized following a published procedure (Ponnusamy et al., 2013; Swaminathan et al., 2015). A mixture of (E)-methyl 2-((2-formylphenoxy)methyl)-3-(2-methylphenyl) acrylate (0.448 g, 1 mmol) and N,N-dimethylbarbutric acid (0.156 g, 1 mmol) was placed in a round-bottom flask and melted at 453 K for 1 h. After completion of the reaction, as indicated by TLC, the crude product was washed with 5 ml of an ethylacetate and hexane mixture (1:49) which successfully provided the pure title compound as a colourless solid in 97% yield. Colourless block-like crystals were obtained by slow evaporation of a solution in ethyl acetate.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
|
Structural data
CCDC reference: 938663
https://doi.org/10.1107/S2414314617008124/su4152sup1.cif
contains datablocks I, Global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617008124/su4152Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617008124/su4152Isup3.cml
Data collection: APEX2 (Bruker, 2004); cell
APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).C25H24N2O6 | F(000) = 944 |
Mr = 448.46 | Dx = 1.394 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.4087 (5) Å | Cell parameters from 3764 reflections |
b = 15.5422 (7) Å | θ = 2.2–25.0° |
c = 14.6143 (7) Å | µ = 0.10 mm−1 |
β = 91.077 (1)° | T = 293 K |
V = 2136.70 (18) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.20 × 0.20 mm |
Bruker Kappa APEXII CCD diffractometer | 3765 independent reflections |
Radiation source: fine-focus sealed tube | 2856 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
ω and \ f scan | θmax = 25.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −11→11 |
Tmin = 0.976, Tmax = 0.980 | k = −18→17 |
18765 measured reflections | l = −17→17 |
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)] = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.146 | w = 1/[σ2(Fo2) + (0.070P)2 + 1.3588P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3764 reflections | Δρmax = 0.38 e Å−3 |
315 parameters | Δρmin = −0.32 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: 0.0027 (9) |
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. 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 > 2sigma(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 | ||
O3 | 0.06395 (16) | 0.17387 (10) | 0.55862 (10) | 0.0347 (4) | |
N2 | −0.09694 (19) | 0.06786 (12) | 0.57179 (12) | 0.0326 (4) | |
O1 | −0.2595 (2) | 0.10497 (11) | 0.32021 (12) | 0.0492 (5) | |
N1 | −0.2602 (2) | 0.03401 (12) | 0.45525 (13) | 0.0366 (5) | |
C6 | −0.0576 (2) | 0.23662 (15) | 0.38555 (15) | 0.0306 (5) | |
O6 | 0.1784 (2) | 0.41781 (11) | 0.42814 (12) | 0.0492 (5) | |
C10 | −0.0494 (2) | 0.13542 (14) | 0.51946 (15) | 0.0300 (5) | |
C8 | −0.2138 (2) | 0.10127 (14) | 0.39882 (16) | 0.0349 (5) | |
C12 | 0.0454 (2) | 0.28986 (14) | 0.44668 (14) | 0.0295 (5) | |
O4 | −0.1355 (2) | 0.40049 (12) | 0.47194 (12) | 0.0492 (5) | |
C9 | −0.2074 (2) | 0.01613 (15) | 0.54146 (16) | 0.0349 (5) | |
O2 | −0.25164 (19) | −0.04286 (11) | 0.58803 (12) | 0.0472 (5) | |
O5 | 0.1608 (2) | 0.33076 (12) | 0.30769 (12) | 0.0525 (5) | |
C5 | −0.1729 (2) | 0.29763 (15) | 0.34819 (15) | 0.0344 (5) | |
C7 | −0.1103 (2) | 0.15883 (14) | 0.43876 (15) | 0.0315 (5) | |
C11 | 0.1479 (2) | 0.22715 (15) | 0.49729 (15) | 0.0303 (5) | |
C14 | −0.2029 (2) | 0.37414 (16) | 0.39255 (16) | 0.0382 (6) | |
C13 | −0.0403 (3) | 0.34201 (16) | 0.51515 (16) | 0.0353 (5) | |
C15 | 0.2642 (2) | 0.26739 (14) | 0.55503 (15) | 0.0327 (5) | |
C22 | 0.1333 (2) | 0.34790 (15) | 0.38504 (15) | 0.0315 (5) | |
C4 | −0.2431 (3) | 0.28342 (17) | 0.26444 (17) | 0.0439 (6) | |
H4 | −0.2236 | 0.2336 | 0.2317 | 0.053* | |
C24 | −0.0344 (3) | 0.04952 (16) | 0.66270 (15) | 0.0380 (6) | |
H24A | 0.0405 | 0.0899 | 0.6758 | 0.057* | |
H24B | 0.0034 | −0.0078 | 0.6635 | 0.057* | |
H24C | −0.1064 | 0.0546 | 0.7081 | 0.057* | |
C1 | −0.2996 (3) | 0.43321 (18) | 0.35660 (19) | 0.0475 (6) | |
H1 | −0.3174 | 0.4842 | 0.3876 | 0.057* | |
C16 | 0.2341 (3) | 0.29708 (16) | 0.64267 (16) | 0.0403 (6) | |
H16 | 0.1439 | 0.2888 | 0.6660 | 0.048* | |
C20 | 0.4013 (2) | 0.27693 (15) | 0.52092 (17) | 0.0385 (6) | |
C19 | 0.5020 (3) | 0.31952 (17) | 0.5762 (2) | 0.0489 (7) | |
H19 | 0.5932 | 0.3275 | 0.5543 | 0.059* | |
C25 | −0.3653 (3) | −0.02591 (18) | 0.4154 (2) | 0.0505 (7) | |
H25A | −0.3938 | −0.0062 | 0.3555 | 0.076* | |
H25B | −0.4469 | −0.0285 | 0.4538 | 0.076* | |
H25C | −0.3239 | −0.0822 | 0.4108 | 0.076* | |
C2 | −0.3682 (3) | 0.4162 (2) | 0.2757 (2) | 0.0545 (7) | |
H2 | −0.4340 | 0.4552 | 0.2518 | 0.065* | |
C18 | 0.4707 (3) | 0.34989 (18) | 0.6618 (2) | 0.0539 (8) | |
H18 | 0.5400 | 0.3779 | 0.6968 | 0.065* | |
C3 | −0.3405 (3) | 0.34127 (19) | 0.2292 (2) | 0.0537 (7) | |
H3 | −0.3875 | 0.3297 | 0.1740 | 0.064* | |
C21 | 0.4458 (3) | 0.24282 (19) | 0.42969 (19) | 0.0507 (7) | |
H21A | 0.3660 | 0.2157 | 0.3996 | 0.076* | |
H21B | 0.5207 | 0.2016 | 0.4385 | 0.076* | |
H21C | 0.4790 | 0.2894 | 0.3926 | 0.076* | |
C17 | 0.3366 (3) | 0.33869 (17) | 0.69537 (18) | 0.0493 (7) | |
H17 | 0.3147 | 0.3590 | 0.7533 | 0.059* | |
C23 | 0.2712 (4) | 0.47395 (19) | 0.3776 (2) | 0.0659 (9) | |
H23A | 0.2979 | 0.5222 | 0.4151 | 0.099* | |
H23B | 0.2225 | 0.4940 | 0.3234 | 0.099* | |
H23C | 0.3549 | 0.4429 | 0.3607 | 0.099* | |
H11 | 0.184 (2) | 0.1876 (15) | 0.4531 (15) | 0.030 (6)* | |
H13A | −0.098 (3) | 0.3021 (16) | 0.5534 (17) | 0.041 (7)* | |
H13B | 0.021 (3) | 0.3788 (15) | 0.5547 (16) | 0.034 (6)* | |
H6 | −0.005 (3) | 0.2172 (16) | 0.3333 (17) | 0.041 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O3 | 0.0319 (8) | 0.0382 (9) | 0.0336 (8) | −0.0091 (7) | −0.0040 (6) | 0.0052 (7) |
N2 | 0.0320 (10) | 0.0322 (10) | 0.0336 (10) | −0.0047 (8) | 0.0013 (8) | 0.0015 (8) |
O1 | 0.0599 (12) | 0.0408 (10) | 0.0461 (10) | −0.0077 (9) | −0.0211 (9) | −0.0007 (8) |
N1 | 0.0338 (10) | 0.0321 (11) | 0.0436 (11) | −0.0057 (8) | −0.0028 (9) | −0.0016 (9) |
C6 | 0.0289 (11) | 0.0336 (12) | 0.0293 (11) | −0.0018 (10) | −0.0004 (9) | −0.0013 (9) |
O6 | 0.0657 (12) | 0.0359 (10) | 0.0465 (10) | −0.0187 (9) | 0.0172 (9) | −0.0055 (8) |
C10 | 0.0272 (11) | 0.0287 (12) | 0.0342 (11) | −0.0017 (9) | 0.0026 (9) | −0.0041 (9) |
C8 | 0.0307 (12) | 0.0308 (12) | 0.0430 (14) | 0.0032 (10) | −0.0039 (10) | −0.0035 (10) |
C12 | 0.0288 (11) | 0.0313 (12) | 0.0284 (11) | −0.0005 (9) | 0.0005 (9) | −0.0008 (9) |
O4 | 0.0545 (11) | 0.0504 (11) | 0.0426 (10) | 0.0210 (9) | −0.0052 (8) | −0.0083 (8) |
C9 | 0.0315 (12) | 0.0312 (12) | 0.0422 (13) | −0.0007 (10) | 0.0062 (10) | −0.0056 (10) |
O2 | 0.0513 (11) | 0.0391 (10) | 0.0513 (11) | −0.0139 (8) | 0.0044 (8) | 0.0037 (8) |
O5 | 0.0651 (12) | 0.0552 (12) | 0.0377 (10) | −0.0163 (9) | 0.0152 (9) | −0.0071 (8) |
C5 | 0.0301 (11) | 0.0366 (13) | 0.0366 (12) | −0.0056 (10) | −0.0008 (9) | 0.0078 (10) |
C7 | 0.0291 (11) | 0.0308 (12) | 0.0346 (12) | 0.0006 (9) | −0.0008 (9) | −0.0013 (9) |
C11 | 0.0296 (11) | 0.0303 (12) | 0.0311 (11) | −0.0037 (9) | 0.0017 (9) | 0.0002 (10) |
C14 | 0.0313 (12) | 0.0438 (14) | 0.0395 (13) | 0.0011 (11) | 0.0038 (10) | 0.0061 (11) |
C13 | 0.0343 (12) | 0.0391 (14) | 0.0326 (12) | 0.0026 (11) | 0.0014 (10) | −0.0011 (11) |
C15 | 0.0339 (12) | 0.0282 (11) | 0.0356 (12) | −0.0036 (10) | −0.0063 (9) | 0.0059 (9) |
C22 | 0.0302 (11) | 0.0316 (12) | 0.0328 (12) | 0.0017 (9) | −0.0008 (9) | 0.0005 (10) |
C4 | 0.0466 (14) | 0.0429 (14) | 0.0418 (14) | −0.0118 (12) | −0.0095 (11) | 0.0076 (11) |
C24 | 0.0397 (13) | 0.0397 (13) | 0.0346 (12) | −0.0006 (11) | 0.0006 (10) | 0.0046 (10) |
C1 | 0.0393 (14) | 0.0476 (16) | 0.0559 (16) | 0.0110 (12) | 0.0044 (12) | 0.0104 (13) |
C16 | 0.0441 (14) | 0.0404 (14) | 0.0362 (13) | −0.0050 (11) | −0.0056 (10) | 0.0050 (10) |
C20 | 0.0329 (12) | 0.0315 (13) | 0.0507 (14) | −0.0021 (10) | −0.0067 (11) | 0.0076 (11) |
C19 | 0.0350 (14) | 0.0432 (15) | 0.0681 (18) | −0.0084 (12) | −0.0124 (12) | 0.0065 (13) |
C25 | 0.0452 (15) | 0.0457 (16) | 0.0603 (17) | −0.0163 (12) | −0.0103 (13) | −0.0052 (13) |
C2 | 0.0393 (14) | 0.0589 (18) | 0.0649 (18) | 0.0016 (13) | −0.0078 (13) | 0.0234 (15) |
C18 | 0.0530 (17) | 0.0423 (15) | 0.0651 (18) | −0.0121 (13) | −0.0291 (14) | 0.0044 (14) |
C3 | 0.0499 (16) | 0.0563 (18) | 0.0541 (16) | −0.0133 (14) | −0.0196 (13) | 0.0192 (14) |
C21 | 0.0340 (13) | 0.0558 (17) | 0.0627 (17) | −0.0026 (12) | 0.0103 (12) | −0.0008 (14) |
C17 | 0.0660 (18) | 0.0420 (15) | 0.0392 (14) | −0.0059 (13) | −0.0160 (13) | 0.0013 (11) |
C23 | 0.082 (2) | 0.0461 (17) | 0.071 (2) | −0.0270 (16) | 0.0298 (17) | −0.0027 (14) |
O3—C10 | 1.341 (3) | C15—C16 | 1.395 (3) |
O3—C11 | 1.462 (3) | C15—C20 | 1.400 (3) |
N2—C10 | 1.379 (3) | C4—C3 | 1.377 (4) |
N2—C9 | 1.380 (3) | C4—H4 | 0.9300 |
N2—C24 | 1.471 (3) | C24—H24A | 0.9600 |
O1—C8 | 1.220 (3) | C24—H24B | 0.9600 |
N1—C9 | 1.374 (3) | C24—H24C | 0.9600 |
N1—C8 | 1.406 (3) | C1—C2 | 1.363 (4) |
N1—C25 | 1.471 (3) | C1—H1 | 0.9300 |
C6—C7 | 1.525 (3) | C16—C17 | 1.383 (4) |
C6—C5 | 1.534 (3) | C16—H16 | 0.9300 |
C6—C12 | 1.545 (3) | C20—C19 | 1.400 (3) |
C6—H6 | 0.97 (3) | C20—C21 | 1.501 (4) |
O6—C22 | 1.322 (3) | C19—C18 | 1.374 (4) |
O6—C23 | 1.447 (3) | C19—H19 | 0.9300 |
C10—C7 | 1.352 (3) | C25—H25A | 0.9600 |
C8—C7 | 1.438 (3) | C25—H25B | 0.9600 |
C12—C22 | 1.529 (3) | C25—H25C | 0.9600 |
C12—C13 | 1.529 (3) | C2—C3 | 1.375 (4) |
C12—C11 | 1.549 (3) | C2—H2 | 0.9300 |
O4—C14 | 1.374 (3) | C18—C17 | 1.374 (4) |
O4—C13 | 1.416 (3) | C18—H18 | 0.9300 |
C9—O2 | 1.220 (3) | C3—H3 | 0.9300 |
O5—C22 | 1.195 (3) | C21—H21A | 0.9600 |
C5—C14 | 1.386 (3) | C21—H21B | 0.9600 |
C5—C4 | 1.398 (3) | C21—H21C | 0.9600 |
C11—C15 | 1.506 (3) | C17—H17 | 0.9300 |
C11—H11 | 0.96 (2) | C23—H23A | 0.9600 |
C14—C1 | 1.389 (3) | C23—H23B | 0.9600 |
C13—H13A | 1.00 (3) | C23—H23C | 0.9600 |
C13—H13B | 0.99 (2) | ||
C10—O3—C11 | 115.14 (16) | O5—C22—O6 | 124.1 (2) |
C10—N2—C9 | 121.06 (19) | O5—C22—C12 | 123.7 (2) |
C10—N2—C24 | 121.35 (18) | O6—C22—C12 | 112.13 (18) |
C9—N2—C24 | 117.58 (19) | C3—C4—C5 | 121.6 (3) |
C9—N1—C8 | 125.24 (19) | C3—C4—H4 | 119.2 |
C9—N1—C25 | 117.7 (2) | C5—C4—H4 | 119.2 |
C8—N1—C25 | 116.9 (2) | N2—C24—H24A | 109.5 |
C7—C6—C5 | 115.91 (18) | N2—C24—H24B | 109.5 |
C7—C6—C12 | 109.63 (17) | H24A—C24—H24B | 109.5 |
C5—C6—C12 | 107.82 (18) | N2—C24—H24C | 109.5 |
C7—C6—H6 | 109.4 (15) | H24A—C24—H24C | 109.5 |
C5—C6—H6 | 106.4 (15) | H24B—C24—H24C | 109.5 |
C12—C6—H6 | 107.3 (15) | C2—C1—C14 | 119.7 (3) |
C22—O6—C23 | 116.34 (19) | C2—C1—H1 | 120.1 |
O3—C10—C7 | 125.0 (2) | C14—C1—H1 | 120.1 |
O3—C10—N2 | 111.50 (18) | C17—C16—C15 | 121.0 (2) |
C7—C10—N2 | 123.5 (2) | C17—C16—H16 | 119.5 |
O1—C8—N1 | 118.7 (2) | C15—C16—H16 | 119.5 |
O1—C8—C7 | 125.2 (2) | C19—C20—C15 | 117.6 (2) |
N1—C8—C7 | 116.1 (2) | C19—C20—C21 | 118.9 (2) |
C22—C12—C13 | 111.75 (19) | C15—C20—C21 | 123.5 (2) |
C22—C12—C6 | 108.39 (17) | C18—C19—C20 | 122.3 (3) |
C13—C12—C6 | 109.27 (18) | C18—C19—H19 | 118.9 |
C22—C12—C11 | 108.27 (17) | C20—C19—H19 | 118.9 |
C13—C12—C11 | 110.61 (17) | N1—C25—H25A | 109.5 |
C6—C12—C11 | 108.47 (17) | N1—C25—H25B | 109.5 |
C14—O4—C13 | 117.59 (18) | H25A—C25—H25B | 109.5 |
O2—C9—N1 | 122.8 (2) | N1—C25—H25C | 109.5 |
O2—C9—N2 | 121.4 (2) | H25A—C25—H25C | 109.5 |
N1—C9—N2 | 115.7 (2) | H25B—C25—H25C | 109.5 |
C14—C5—C4 | 116.6 (2) | C1—C2—C3 | 120.1 (3) |
C14—C5—C6 | 120.9 (2) | C1—C2—H2 | 119.9 |
C4—C5—C6 | 122.3 (2) | C3—C2—H2 | 119.9 |
C10—C7—C8 | 117.4 (2) | C19—C18—C17 | 119.7 (2) |
C10—C7—C6 | 121.44 (19) | C19—C18—H18 | 120.1 |
C8—C7—C6 | 120.69 (19) | C17—C18—H18 | 120.1 |
O3—C11—C15 | 106.67 (17) | C2—C3—C4 | 120.0 (3) |
O3—C11—C12 | 108.09 (17) | C2—C3—H3 | 120.0 |
C15—C11—C12 | 116.47 (18) | C4—C3—H3 | 120.0 |
O3—C11—H11 | 104.7 (13) | C20—C21—H21A | 109.5 |
C15—C11—H11 | 112.3 (14) | C20—C21—H21B | 109.5 |
C12—C11—H11 | 107.9 (13) | H21A—C21—H21B | 109.5 |
O4—C14—C5 | 123.8 (2) | C20—C21—H21C | 109.5 |
O4—C14—C1 | 114.3 (2) | H21A—C21—H21C | 109.5 |
C5—C14—C1 | 121.9 (2) | H21B—C21—H21C | 109.5 |
O4—C13—C12 | 112.64 (18) | C18—C17—C16 | 119.7 (3) |
O4—C13—H13A | 107.6 (14) | C18—C17—H17 | 120.1 |
C12—C13—H13A | 109.6 (14) | C16—C17—H17 | 120.1 |
O4—C13—H13B | 104.3 (13) | O6—C23—H23A | 109.5 |
C12—C13—H13B | 112.2 (14) | O6—C23—H23B | 109.5 |
H13A—C13—H13B | 110.3 (19) | H23A—C23—H23B | 109.5 |
C16—C15—C20 | 119.7 (2) | O6—C23—H23C | 109.5 |
C16—C15—C11 | 119.6 (2) | H23A—C23—H23C | 109.5 |
C20—C15—C11 | 120.6 (2) | H23B—C23—H23C | 109.5 |
C11—O3—C10—C7 | −17.9 (3) | C6—C12—C11—O3 | −64.6 (2) |
C11—O3—C10—N2 | 161.80 (17) | C22—C12—C11—C15 | 58.0 (2) |
C9—N2—C10—O3 | −176.06 (18) | C13—C12—C11—C15 | −64.8 (2) |
C24—N2—C10—O3 | 5.4 (3) | C6—C12—C11—C15 | 175.43 (18) |
C9—N2—C10—C7 | 3.7 (3) | C13—O4—C14—C5 | −6.5 (3) |
C24—N2—C10—C7 | −174.8 (2) | C13—O4—C14—C1 | 177.0 (2) |
C9—N1—C8—O1 | 172.7 (2) | C4—C5—C14—O4 | −175.2 (2) |
C25—N1—C8—O1 | −1.9 (3) | C6—C5—C14—O4 | −0.9 (3) |
C9—N1—C8—C7 | −4.9 (3) | C4—C5—C14—C1 | 1.0 (3) |
C25—N1—C8—C7 | −179.6 (2) | C6—C5—C14—C1 | 175.3 (2) |
C7—C6—C12—C22 | 161.32 (18) | C14—O4—C13—C12 | 37.6 (3) |
C5—C6—C12—C22 | −71.7 (2) | C22—C12—C13—O4 | 59.2 (3) |
C7—C6—C12—C13 | −76.7 (2) | C6—C12—C13—O4 | −60.8 (3) |
C5—C6—C12—C13 | 50.3 (2) | C11—C12—C13—O4 | 179.87 (19) |
C7—C6—C12—C11 | 44.0 (2) | O3—C11—C15—C16 | −40.0 (3) |
C5—C6—C12—C11 | 170.98 (17) | C12—C11—C15—C16 | 80.7 (3) |
C8—N1—C9—O2 | 179.7 (2) | O3—C11—C15—C20 | 141.4 (2) |
C25—N1—C9—O2 | −5.7 (3) | C12—C11—C15—C20 | −97.9 (3) |
C8—N1—C9—N2 | −2.2 (3) | C23—O6—C22—O5 | −2.5 (4) |
C25—N1—C9—N2 | 172.5 (2) | C23—O6—C22—C12 | 175.7 (2) |
C10—N2—C9—O2 | −178.8 (2) | C13—C12—C22—O5 | −148.4 (2) |
C24—N2—C9—O2 | −0.2 (3) | C6—C12—C22—O5 | −28.0 (3) |
C10—N2—C9—N1 | 3.1 (3) | C11—C12—C22—O5 | 89.5 (3) |
C24—N2—C9—N1 | −178.36 (19) | C13—C12—C22—O6 | 33.4 (3) |
C7—C6—C5—C14 | 100.9 (2) | C6—C12—C22—O6 | 153.82 (19) |
C12—C6—C5—C14 | −22.3 (3) | C11—C12—C22—O6 | −88.7 (2) |
C7—C6—C5—C4 | −85.1 (3) | C14—C5—C4—C3 | −2.0 (4) |
C12—C6—C5—C4 | 151.6 (2) | C6—C5—C4—C3 | −176.2 (2) |
O3—C10—C7—C8 | 168.8 (2) | O4—C14—C1—C2 | 176.9 (2) |
N2—C10—C7—C8 | −10.9 (3) | C5—C14—C1—C2 | 0.3 (4) |
O3—C10—C7—C6 | −3.1 (3) | C20—C15—C16—C17 | 2.3 (4) |
N2—C10—C7—C6 | 177.24 (19) | C11—C15—C16—C17 | −176.3 (2) |
O1—C8—C7—C10 | −166.4 (2) | C16—C15—C20—C19 | −2.4 (3) |
N1—C8—C7—C10 | 11.0 (3) | C11—C15—C20—C19 | 176.2 (2) |
O1—C8—C7—C6 | 5.5 (3) | C16—C15—C20—C21 | 176.6 (2) |
N1—C8—C7—C6 | −177.04 (19) | C11—C15—C20—C21 | −4.8 (4) |
C5—C6—C7—C10 | −134.2 (2) | C15—C20—C19—C18 | 1.3 (4) |
C12—C6—C7—C10 | −11.9 (3) | C21—C20—C19—C18 | −177.7 (2) |
C5—C6—C7—C8 | 54.2 (3) | C14—C1—C2—C3 | −0.9 (4) |
C12—C6—C7—C8 | 176.55 (19) | C20—C19—C18—C17 | 0.0 (4) |
C10—O3—C11—C15 | 177.27 (18) | C1—C2—C3—C4 | −0.1 (4) |
C10—O3—C11—C12 | 51.3 (2) | C5—C4—C3—C2 | 1.5 (4) |
C22—C12—C11—O3 | 177.98 (16) | C19—C18—C17—C16 | −0.1 (4) |
C13—C12—C11—O3 | 55.2 (2) | C15—C16—C17—C18 | −1.1 (4) |
Cg3 and Cg4 are the centroids of the N1/N2/C7–C10 and C1–C5/C14 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11···O2i | 0.96 (2) | 2.42 (2) | 3.280 (3) | 150 (2) |
C18—H18···O1ii | 0.93 | 2.60 | 3.475 (3) | 157 |
C23—H23A···O4iii | 0.96 | 2.57 | 3.222 (4) | 125 |
C24—H24A···O5iv | 0.96 | 2.54 | 3.344 (3) | 142 |
C21—H21C···Cg4v | 0.96 | 2.86 | 3.668 (3) | 143 |
C24—H24B···Cg3i | 0.96 | 2.92 | 3.550 (3) | 124 |
C24—H24C···Cg4iv | 0.96 | 2.57 | 3.454 (3) | 153 |
Symmetry codes: (i) −x, −y, −z+1; (ii) x+1, −y+1/2, z+1/2; (iii) −x, −y+1, −z+1; (iv) x, −y+1/2, z+1/2; (v) x+1, y, z. |
Acknowledgements
The authors thank the Central Instrumentation Facility, Queen Mary's College, Chennai-4 for computing facilities and SAIF, IIT, Madras, for the X-ray data collection facility.
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