research communications
Crystal structures and conformational analyses of three pyranochromene derivatives
aDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: ksethusankar@yahoo.co.in
The title compounds, C27H20O6, (I) [systematic name: methyl 7-oxo-14-phenyl-1H,7H,14H-pyrano[3,2-c:5,4-c′]dichromene-14a(6bH)-carboxylate], C24H22O5, (II) [systematic name: methyl 1-oxo-6-phenyl-2,3,4,12b-tetrahydro-1H,6H-chromeno[3,4-c]chromene-6a(7H)-carboxylate], and C25H23N3O4, (III) [systematic name: 6-(4-ethylphenyl)-2,4-dimethyl-1,3-dioxo-2,3,4,12b-tetrahydro-1H,6H-chromeno[4′,3′:4,5]pyrano[2,3-d]pyrimidine-6a(7H)-carbonitrile], are pyranochromene derivatives. The central pyran rings (B) of compounds (I) and (III) adopt half-chair conformations, whereas that of compound (II) adopts a sofa conformation. The pyran rings (A) of the chromene ring systems of compounds (II) and (III) adopt half-chair conformations, while that of compound (I) adopts a sofa conformation. The mean plane of the central pyran rings (B) make dihedral angles of 70.02 (6), 61.52 (6) and 69.12 (7)°, respectively, with the mean planes of the chromene moieties (C+A) of compounds (I), (II) and (III). The bicyclic coumarin ring system (C+A+B+E) in compound (I) is almost planar (r.m.s. deviation = 0.042 Å). The carbonitrile side chain in compound (III) is very nearly linear, with the C—C≡N angle being 176.6 (2)°. The cyclohexene ring (E), fused with the central pyran ring (B) in compound (II) adopts a sofa conformation. In the molecular structures of compounds (II) and (III), there are C—H⋯O short contacts, which generate S(7) ring motifs. In the crystal structures of the title compounds, molecules are linked by C—H⋯O hydrogen bonds, which generate molecular sheets parallel to the ab plane, with R43(28) loops in (I), inversion dimers with R22(10) loops in (II) and chains along [010] with R22(12) ring motifs in (III). In the crystal structures of (I) and (III), there are also C—H⋯π interactions present, leading to the formation of a three-dimensional framework in (II) and to sheets parallel to (101) in (III).
1. Chemical context
Chromenes, the oxygen-containing heterocyclic scaffolds, represent a privileged structural motif, well distributed in biologically active natural products and also in synthetic compounds used in the fields of medicine, agrochemistry, cosmetics and pigments. A number of drugs containing chromene are used in the treatment of ailments such as hypertension, asthma, ischemia and urinary incontinence. Chromene derivatives are known to possess antitumor, antivascular (Gourdeau et al., 2004), antimicrobial (Sangani et al., 2012), anti-oxidant (Mladenović et al., 2011), antifungal (Thareja et al., 2010), antiviral (Smith et al., 1998), anti-inflammatory (Moon et al., 2007), antimalarial (de Andrade-Neto et al., 2004), sex hormonal (Mohr et al., 1975), antiproliferative (Bianchi & Tava, 1987), anticancer, anti-Alzheimer, anti-Parkinson and Huntington's diseases (Andrani & Lapi, 1960; Zhang et al., 1982), Tumor Necrosis Factor (TNF–α) inhibitory (Cheng et al., 2003), estrogenic (Jain et al., 2009), antifilaricidal (Tripathi et al., 2000) and anticonvulsant (Bhat et al., 2008) activities.
Chromene derivatives also play an important role in the production of highly effective fluorescent dyes for synthetic fibers, daylight-fluorescent pigments and electrophotographic and electroluminescent devices (Khairy et al., 2009). Against this background, the title compounds, (I), (II) and (III), were synthesized and we report herein on their crystal structures and molecular conformations.
2. Structural commentary
The molecular structures of compounds, (I), (II) and (III) are illustrated in Figs. 1, 2 and 3, respectively. All three compounds comprise a central pyran ring (B) fused with a chromene ring system (C+A). The central pyran ring (B) is fused with a second chromene ring system (E+F) in (I), a cyclohexene ring (E) in (II) and a pyrimidine ring (E) in (III); see scheme and Figs. 1–3. In compounds (I) and (II), a carboxylate side chain and a benzene ring (D) are attached to the central pyran ring (B), in adjacent positions, whereas in (III) there is a cabonitrile side chain and an ethyl-substituted benzene ring attached to the central pyran ring (B).
In compounds (I) and (III), the central pyran rings (B) adopt half-chair conformations with puckering amplitudes Q = 0.5166 (15) Å, θ = 51.22 (17), φ = 259.4 (2)° and Q = 0.486 (2) Å, θ = 128.3 (2), φ = 74.5 (3)°, respectively. In compound (II), the central pyran ring (B) adopts a sofa conformation [Q = 0.5614 (15) Å, θ = 58.41 (15), φ = 286.21 (16)°]. The cyclohexene ring (E) fused to the central pyran ring (B) in compound (II), adopts a sofa conformation [Q = 0.497 (2) Å, θ = 109.8 (2), φ = 5.9 (2)°]. The pyran ring (A) of the chromene moiety adopts a half-chair conformation in compounds (II) and (III) [Q = 0.4850 (14) Å, θ = 53.26 (17), φ = 271.70 (19)° and Q = 0.507 (2) Å, θ = 128.9 (2), φ = 92.7 (3)°, respectively] and a sofa conformation in compound (I) [Q = 0.5130 (16) Å, θ = 57.83 (18), φ = 234.6 (2)°].
In compound (I), the dihedral angle between the benzene ring (C) and the mean plane of the pyran ring (A – sofa conformation) of the chromene moiety is 14.95 (8)°, whereas in (II) and (III) the same angles are 7.83 (7) and 6.42 (10)°, respectively (the A rings here have half-chair conformations). The decrease in the value of the dihedral angle in compounds (II) and (III) is probably due to the intramolecular C—H⋯O short contacts which generate S(7) ring motifs. The second coumarin ring system (E+F) is almost planar with the dihedral angle between the pyran and benzene rings being 3.73 (7)°. Atom O4 deviates from the mean plane of this coumarin ring system by 0.111 (1) Å. The phenyl ring (D) is inclined to the mean plane of the central pyran ring (B), by 60.48 (8)°.
In compound (II), the mean plane of the central pyran ring (B) makes dihedral angles of 22.63 (8) and 56.99 (9)° with the mean plane of the six-membered carbocylic ring (E) and the phenyl ring (D), respectively. Atom O3 deviates from the mean plane of ring (E) by 0.199 (1) Å.
In compound (III), the central pyran ring (B) makes dihedral angles of 7.36 (9) and 58.24 (10)° with the pyrimidine (E) and ethyl-substituted benzene (D) rings, respectively. Atom O3 and the methyl group C atom, C16, deviate significantly from the mean plane of the pyrimidine ring (E) by 0.106 (1) and −0.107 (2) Å, respectively.
3. Supramolecular features
In compound (I), C—H⋯O hydrogen bonds are present in which the carboxylate and chromene ring C atoms, C27 and C1, respectively, act as donors and the coumarin ring O atom, O4, acts as a single acceptor (Table 1). These hydrogen bonds link the molecules into (28) ring motifs, resulting in the formation of sheets parallel to the ab plane (Fig. 4). The sheets are linked by C—H⋯π interactions, forming a three-dimensional framework (Table 1).
In compound (II), molecules are linked through pairs of C–H⋯O hydrogen bonds, resulting in the formation of inversion dimers with graph-set motif (10) (Table 2 and Fig. 5).
|
In compound (III), molecules are linked through C—H⋯O hydrogen bonds, resulting in the formation chains along the b-axis direction, enclosing (12) ring motifs (Fig. 6). The chains are linked by C—H⋯π interactions, forming sheets parallel to (101) (Table 3).
|
4. Database survey
A search of the Cambridge Structural Database (Version 5.36, last update February 2015; Groom & Allen, 2014) for 4,4a,5,10b-tetrahydro-4-phenylpyrano[3,4-c]chromene yielded 14 hits. The bond distances and bond angles in compounds (I)–(III) are in agreement with those in the reported structures. For example: compounds (I) and (II) exhibits structural similarities with entries LESWIR (Ponnusamy et al., 2013) which has a toluene rather than a phenyl substituent on ring (B), OLEZIP (Kathiravan & Raghunathan, 2010) which has a 4-methoxyphenyl substituent, and AZUKIQ (Swaminathan et al., 2011) which has a 2-chlorophenyl substituent. Compound (III) is similar to entries WUNNAV (Bakthadoss et al., 2009), AXACAE (Kanchanadevi et al., 2011) and WUNNEZ (Bakthadoss et al., 2009), but only the last compound also has a cabonitrile side chain.
5. Synthesis and crystallization
Compound (I): A mixture of (E)-methyl 2-[(2-formylphenoxy)methyl]-3-phenylacrylate (0.296 g, 1 mmol) and 4-hydroxy-2H -chromen-2-one (0.162 g, 1 mmol) was placed in a round bottom flask and heated at 453 K for 1 h. After completion of the reaction as indicated by TLC, the crude product was washed with 5 ml of ethylacetate and hexane mixture (1:49 ratio) which successfully provided compound (I) as a colourless solid. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of (I) in ethylacetate at room temperature.
Compound (II): A mixture of (E)-methyl 2-[(2-formylphenoxy)methyl]-3-phenylacrylate (0.296 g, 1 mmol) and cyclohexane-1,3-dione (0.112 g, 1 mmol) was placed in a round bottom flask and heated at 453 K for 1 h. After completion of the reaction as indicated by TLC, the crude product was washed with 5 ml of ethylacetate and hexane mixture (1:49 ratio) which successfully provided the crude product of compound (II) as a colourless solid. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of (II) in ethylacetate at room temperature.
Compound (III): A mixture of (E)-2-[(2-formylphenoxy)methyl]-3-(4-ethylphenyl)acrylonitrile (0.291 g, 1 mmol) and 1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione (0.156 g, 1 mmol) was placed in a round-bottom flask and heated at 453 K for 1 h. After completion of the reaction as indicated by TLC, the crude product was washed with 5 ml of ethylacetate and hexane mixture (1:49 ratio) which successfully provided pure compound (III) as a colourless solid. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of (III) in ethylacetate at room temperature.
6. Refinement
Crystal data, data collection and structure , (II) and (III) are summarized in Table 4. The positions of all of the H atoms were located in difference electron density maps. During they were treated as riding atoms, with d(C—H) = 0.93, 0.96, 0.97 and 0.98 Å for aryl, methyl, methylene and methine H atoms, respectively, and with Uiso(H)= 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for other H atoms.
details for compounds (I)
|
Supporting information
https://doi.org/10.1107/S2056989015012967/su5160sup1.cif
contains datablocks I, II, III, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015012967/su5160Isup2.hkl
Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989015012967/su5160IIsup3.hkl
Structure factors: contains datablock III. DOI: https://doi.org/10.1107/S2056989015012967/su5160IIIsup4.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015012967/su5160Isup5.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989015012967/su5160IIsup6.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989015012967/su5160IIIsup7.cml
For all compounds, data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).C27H20O6 | F(000) = 920 |
Mr = 440.43 | Dx = 1.391 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3698 reflections |
a = 9.3980 (15) Å | θ = 2.6–25.0° |
b = 14.0050 (12) Å | µ = 0.10 mm−1 |
c = 15.9890 (13) Å | T = 296 K |
β = 92.048 (5)° | Block, colourless |
V = 2103.1 (4) Å3 | 0.35 × 0.30 × 0.25 mm |
Z = 4 |
Bruker Kappa APEXII CCD diffractometer | 3698 independent reflections |
Radiation source: fine-focus sealed tube | 2964 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ω & φ scans | θmax = 25.0°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −11→11 |
Tmin = 0.966, Tmax = 0.976 | k = −16→16 |
19091 measured reflections | l = −19→19 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0556P)2 + 0.3545P] where P = (Fo2 + 2Fc2)/3 |
3698 reflections | (Δ/σ)max < 0.001 |
299 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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 | ||
C1 | 0.56782 (17) | 0.20825 (13) | 0.27702 (12) | 0.0602 (5) | |
H1 | 0.5188 | 0.1513 | 0.2680 | 0.072* | |
C2 | 0.55034 (19) | 0.25923 (16) | 0.34916 (12) | 0.0673 (5) | |
H2 | 0.4893 | 0.2366 | 0.3892 | 0.081* | |
C3 | 0.6227 (2) | 0.34377 (16) | 0.36281 (11) | 0.0641 (5) | |
H3 | 0.6102 | 0.3782 | 0.4117 | 0.077* | |
C4 | 0.71382 (17) | 0.37705 (13) | 0.30365 (10) | 0.0527 (4) | |
H4 | 0.7636 | 0.4335 | 0.3136 | 0.063* | |
C5 | 0.73273 (15) | 0.32771 (11) | 0.22924 (9) | 0.0418 (3) | |
C6 | 0.65935 (16) | 0.24239 (11) | 0.21752 (10) | 0.0472 (4) | |
C7 | 0.77878 (16) | 0.20819 (11) | 0.09054 (10) | 0.0473 (4) | |
H7A | 0.7343 | 0.2434 | 0.0444 | 0.057* | |
H7B | 0.8165 | 0.1494 | 0.0682 | 0.057* | |
C8 | 0.90161 (15) | 0.26711 (10) | 0.12772 (9) | 0.0382 (3) | |
C9 | 0.84184 (14) | 0.35891 (10) | 0.16676 (9) | 0.0373 (3) | |
H9 | 0.9199 | 0.3912 | 0.1977 | 0.045* | |
C10 | 0.79072 (15) | 0.42388 (10) | 0.09597 (9) | 0.0377 (3) | |
C11 | 0.83533 (15) | 0.41354 (10) | 0.01665 (9) | 0.0390 (3) | |
C12 | 1.00608 (15) | 0.29584 (10) | 0.05912 (9) | 0.0398 (3) | |
H12 | 1.0776 | 0.3390 | 0.0844 | 0.048* | |
C13 | 0.69743 (15) | 0.50314 (10) | 0.11408 (10) | 0.0406 (3) | |
C14 | 0.68064 (15) | 0.54090 (10) | −0.03296 (10) | 0.0436 (4) | |
C15 | 0.78006 (15) | 0.47146 (10) | −0.05170 (9) | 0.0416 (3) | |
C16 | 0.81551 (18) | 0.45965 (12) | −0.13507 (10) | 0.0519 (4) | |
H16 | 0.8829 | 0.4143 | −0.1490 | 0.062* | |
C17 | 0.7513 (2) | 0.51477 (13) | −0.19664 (11) | 0.0594 (5) | |
H17 | 0.7757 | 0.5067 | −0.2521 | 0.071* | |
C18 | 0.65055 (19) | 0.58214 (13) | −0.17657 (12) | 0.0592 (5) | |
H18 | 0.6063 | 0.6183 | −0.2188 | 0.071* | |
C19 | 0.61517 (17) | 0.59612 (12) | −0.09496 (11) | 0.0534 (4) | |
H19 | 0.5482 | 0.6420 | −0.0815 | 0.064* | |
C20 | 1.08306 (16) | 0.21352 (10) | 0.01989 (9) | 0.0437 (4) | |
C21 | 1.21663 (18) | 0.18833 (12) | 0.05144 (12) | 0.0557 (4) | |
H21 | 1.2581 | 0.2227 | 0.0957 | 0.067* | |
C22 | 1.2892 (2) | 0.11241 (13) | 0.01770 (14) | 0.0712 (6) | |
H22 | 1.3792 | 0.0961 | 0.0393 | 0.085* | |
C23 | 1.2289 (2) | 0.06125 (13) | −0.04743 (15) | 0.0754 (6) | |
H23 | 1.2784 | 0.0108 | −0.0706 | 0.091* | |
C24 | 1.0960 (2) | 0.08450 (14) | −0.07837 (13) | 0.0715 (6) | |
H24 | 1.0545 | 0.0487 | −0.1217 | 0.086* | |
C25 | 1.0226 (2) | 0.16088 (12) | −0.04583 (11) | 0.0572 (4) | |
H25 | 0.9329 | 0.1769 | −0.0680 | 0.069* | |
C26 | 0.98572 (15) | 0.20813 (11) | 0.19238 (9) | 0.0423 (4) | |
C27 | 1.1726 (2) | 0.21330 (15) | 0.29418 (13) | 0.0713 (5) | |
H27A | 1.1191 | 0.1816 | 0.3360 | 0.107* | |
H27B | 1.2367 | 0.2584 | 0.3206 | 0.107* | |
H27C | 1.2261 | 0.1670 | 0.2641 | 0.107* | |
O1 | 0.67314 (12) | 0.18517 (9) | 0.14893 (8) | 0.0638 (3) | |
O2 | 0.93013 (11) | 0.34696 (7) | −0.00690 (6) | 0.0466 (3) | |
O3 | 0.64390 (11) | 0.55763 (7) | 0.04799 (7) | 0.0490 (3) | |
O4 | 0.66214 (12) | 0.52699 (8) | 0.18248 (7) | 0.0533 (3) | |
O5 | 1.07607 (11) | 0.26285 (8) | 0.23656 (7) | 0.0535 (3) | |
O6 | 0.97557 (13) | 0.12343 (8) | 0.20042 (8) | 0.0613 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0410 (9) | 0.0613 (11) | 0.0790 (13) | 0.0020 (8) | 0.0107 (8) | 0.0229 (10) |
C2 | 0.0509 (10) | 0.0891 (15) | 0.0631 (11) | 0.0121 (10) | 0.0165 (9) | 0.0304 (11) |
C3 | 0.0585 (11) | 0.0886 (14) | 0.0459 (9) | 0.0167 (10) | 0.0109 (8) | 0.0091 (9) |
C4 | 0.0509 (9) | 0.0614 (10) | 0.0459 (9) | 0.0092 (8) | 0.0045 (7) | 0.0014 (8) |
C5 | 0.0351 (7) | 0.0456 (8) | 0.0450 (8) | 0.0042 (6) | 0.0036 (6) | 0.0054 (7) |
C6 | 0.0362 (8) | 0.0487 (9) | 0.0570 (9) | 0.0018 (7) | 0.0052 (7) | 0.0070 (8) |
C7 | 0.0492 (9) | 0.0389 (8) | 0.0540 (9) | −0.0077 (7) | 0.0055 (7) | −0.0035 (7) |
C8 | 0.0379 (8) | 0.0322 (7) | 0.0448 (8) | −0.0014 (6) | 0.0049 (6) | −0.0016 (6) |
C9 | 0.0339 (7) | 0.0345 (7) | 0.0435 (8) | −0.0020 (6) | 0.0033 (6) | −0.0032 (6) |
C10 | 0.0347 (7) | 0.0305 (7) | 0.0480 (8) | −0.0041 (6) | 0.0031 (6) | −0.0022 (6) |
C11 | 0.0383 (8) | 0.0297 (7) | 0.0492 (8) | −0.0024 (6) | 0.0043 (6) | −0.0021 (6) |
C12 | 0.0419 (8) | 0.0325 (7) | 0.0452 (8) | 0.0012 (6) | 0.0054 (6) | 0.0000 (6) |
C13 | 0.0369 (8) | 0.0310 (7) | 0.0539 (9) | −0.0045 (6) | 0.0043 (7) | −0.0021 (7) |
C14 | 0.0391 (8) | 0.0353 (8) | 0.0565 (9) | −0.0069 (6) | 0.0026 (7) | 0.0040 (7) |
C15 | 0.0423 (8) | 0.0328 (7) | 0.0496 (8) | −0.0055 (6) | 0.0004 (6) | 0.0025 (6) |
C16 | 0.0613 (10) | 0.0441 (9) | 0.0504 (9) | −0.0021 (8) | 0.0028 (8) | 0.0013 (7) |
C17 | 0.0722 (12) | 0.0556 (11) | 0.0502 (10) | −0.0088 (9) | −0.0026 (8) | 0.0078 (8) |
C18 | 0.0573 (11) | 0.0555 (10) | 0.0640 (11) | −0.0090 (8) | −0.0109 (9) | 0.0172 (9) |
C19 | 0.0427 (9) | 0.0417 (9) | 0.0754 (12) | −0.0030 (7) | −0.0057 (8) | 0.0122 (8) |
C20 | 0.0482 (9) | 0.0331 (8) | 0.0506 (9) | 0.0006 (6) | 0.0143 (7) | −0.0004 (6) |
C21 | 0.0492 (9) | 0.0460 (9) | 0.0726 (11) | 0.0017 (7) | 0.0099 (8) | −0.0053 (8) |
C22 | 0.0588 (11) | 0.0527 (11) | 0.1033 (16) | 0.0151 (9) | 0.0186 (11) | −0.0025 (11) |
C23 | 0.0884 (15) | 0.0408 (10) | 0.0995 (15) | 0.0114 (10) | 0.0372 (13) | −0.0086 (10) |
C24 | 0.0917 (15) | 0.0526 (11) | 0.0717 (12) | −0.0006 (10) | 0.0222 (11) | −0.0203 (9) |
C25 | 0.0646 (11) | 0.0512 (10) | 0.0562 (10) | 0.0034 (8) | 0.0090 (8) | −0.0096 (8) |
C26 | 0.0421 (8) | 0.0382 (8) | 0.0473 (8) | 0.0019 (6) | 0.0103 (7) | 0.0024 (7) |
C27 | 0.0585 (11) | 0.0751 (13) | 0.0790 (13) | 0.0166 (10) | −0.0165 (10) | 0.0123 (10) |
O1 | 0.0535 (7) | 0.0599 (7) | 0.0789 (8) | −0.0232 (6) | 0.0172 (6) | −0.0120 (6) |
O2 | 0.0547 (6) | 0.0411 (6) | 0.0446 (6) | 0.0104 (5) | 0.0106 (5) | 0.0027 (5) |
O3 | 0.0476 (6) | 0.0384 (6) | 0.0613 (7) | 0.0071 (5) | 0.0075 (5) | 0.0049 (5) |
O4 | 0.0592 (7) | 0.0416 (6) | 0.0596 (7) | 0.0046 (5) | 0.0112 (5) | −0.0091 (5) |
O5 | 0.0465 (6) | 0.0464 (6) | 0.0667 (7) | 0.0061 (5) | −0.0100 (5) | 0.0041 (5) |
O6 | 0.0759 (8) | 0.0385 (7) | 0.0699 (8) | 0.0000 (6) | 0.0059 (6) | 0.0120 (6) |
C1—C2 | 1.372 (3) | C13—O3 | 1.3835 (18) |
C1—C6 | 1.390 (2) | C14—O3 | 1.3715 (18) |
C1—H1 | 0.9300 | C14—C19 | 1.384 (2) |
C2—C3 | 1.379 (3) | C14—C15 | 1.389 (2) |
C2—H2 | 0.9300 | C15—C16 | 1.395 (2) |
C3—C4 | 1.379 (2) | C16—C17 | 1.374 (2) |
C3—H3 | 0.9300 | C16—H16 | 0.9300 |
C4—C5 | 1.393 (2) | C17—C18 | 1.382 (3) |
C4—H4 | 0.9300 | C17—H17 | 0.9300 |
C5—C6 | 1.389 (2) | C18—C19 | 1.372 (3) |
C5—C9 | 1.5211 (19) | C18—H18 | 0.9300 |
C6—O1 | 1.368 (2) | C19—H19 | 0.9300 |
C7—O1 | 1.4239 (19) | C20—C21 | 1.382 (2) |
C7—C8 | 1.522 (2) | C20—C25 | 1.388 (2) |
C7—H7A | 0.9700 | C21—C22 | 1.383 (2) |
C7—H7B | 0.9700 | C21—H21 | 0.9300 |
C8—C26 | 1.522 (2) | C22—C23 | 1.370 (3) |
C8—C9 | 1.5438 (19) | C22—H22 | 0.9300 |
C8—C12 | 1.5512 (19) | C23—C24 | 1.366 (3) |
C9—C10 | 1.517 (2) | C23—H23 | 0.9300 |
C9—H9 | 0.9800 | C24—C25 | 1.385 (2) |
C10—C11 | 1.358 (2) | C24—H24 | 0.9300 |
C10—C13 | 1.450 (2) | C25—H25 | 0.9300 |
C11—O2 | 1.3524 (17) | C26—O6 | 1.1973 (18) |
C11—C15 | 1.443 (2) | C26—O5 | 1.3283 (18) |
C12—O2 | 1.4430 (17) | C27—O5 | 1.4470 (19) |
C12—C20 | 1.5094 (19) | C27—H27A | 0.9600 |
C12—H12 | 0.9800 | C27—H27B | 0.9600 |
C13—O4 | 1.2015 (17) | C27—H27C | 0.9600 |
C2—C1—C6 | 119.48 (18) | O3—C13—C10 | 118.41 (13) |
C2—C1—H1 | 120.3 | O3—C14—C19 | 117.38 (14) |
C6—C1—H1 | 120.3 | O3—C14—C15 | 121.15 (13) |
C1—C2—C3 | 120.46 (16) | C19—C14—C15 | 121.47 (15) |
C1—C2—H2 | 119.8 | C14—C15—C16 | 118.34 (14) |
C3—C2—H2 | 119.8 | C14—C15—C11 | 117.20 (14) |
C2—C3—C4 | 119.76 (18) | C16—C15—C11 | 124.41 (14) |
C2—C3—H3 | 120.1 | C17—C16—C15 | 120.28 (16) |
C4—C3—H3 | 120.1 | C17—C16—H16 | 119.9 |
C3—C4—C5 | 121.29 (18) | C15—C16—H16 | 119.9 |
C3—C4—H4 | 119.4 | C16—C17—C18 | 120.28 (17) |
C5—C4—H4 | 119.4 | C16—C17—H17 | 119.9 |
C6—C5—C4 | 117.66 (14) | C18—C17—H17 | 119.9 |
C6—C5—C9 | 120.11 (13) | C19—C18—C17 | 120.62 (16) |
C4—C5—C9 | 121.88 (14) | C19—C18—H18 | 119.7 |
O1—C6—C5 | 123.45 (13) | C17—C18—H18 | 119.7 |
O1—C6—C1 | 115.20 (15) | C18—C19—C14 | 119.00 (16) |
C5—C6—C1 | 121.34 (16) | C18—C19—H19 | 120.5 |
O1—C7—C8 | 113.79 (13) | C14—C19—H19 | 120.5 |
O1—C7—H7A | 108.8 | C21—C20—C25 | 118.86 (14) |
C8—C7—H7A | 108.8 | C21—C20—C12 | 119.07 (14) |
O1—C7—H7B | 108.8 | C25—C20—C12 | 122.05 (14) |
C8—C7—H7B | 108.8 | C20—C21—C22 | 120.54 (18) |
H7A—C7—H7B | 107.7 | C20—C21—H21 | 119.7 |
C7—C8—C26 | 109.83 (12) | C22—C21—H21 | 119.7 |
C7—C8—C9 | 109.12 (12) | C23—C22—C21 | 120.14 (19) |
C26—C8—C9 | 111.40 (11) | C23—C22—H22 | 119.9 |
C7—C8—C12 | 110.78 (12) | C21—C22—H22 | 119.9 |
C26—C8—C12 | 107.13 (11) | C24—C23—C22 | 119.91 (17) |
C9—C8—C12 | 108.57 (11) | C24—C23—H23 | 120.0 |
C10—C9—C5 | 117.35 (11) | C22—C23—H23 | 120.0 |
C10—C9—C8 | 107.94 (11) | C23—C24—C25 | 120.64 (19) |
C5—C9—C8 | 106.85 (11) | C23—C24—H24 | 119.7 |
C10—C9—H9 | 108.1 | C25—C24—H24 | 119.7 |
C5—C9—H9 | 108.1 | C24—C25—C20 | 119.90 (18) |
C8—C9—H9 | 108.1 | C24—C25—H25 | 120.0 |
C11—C10—C13 | 118.51 (13) | C20—C25—H25 | 120.0 |
C11—C10—C9 | 122.20 (12) | O6—C26—O5 | 124.50 (15) |
C13—C10—C9 | 119.20 (12) | O6—C26—C8 | 124.68 (14) |
O2—C11—C10 | 124.21 (13) | O5—C26—C8 | 110.77 (12) |
O2—C11—C15 | 113.56 (12) | O5—C27—H27A | 109.5 |
C10—C11—C15 | 122.19 (13) | O5—C27—H27B | 109.5 |
O2—C12—C20 | 107.87 (11) | H27A—C27—H27B | 109.5 |
O2—C12—C8 | 109.69 (11) | O5—C27—H27C | 109.5 |
C20—C12—C8 | 114.87 (11) | H27A—C27—H27C | 109.5 |
O2—C12—H12 | 108.1 | H27B—C27—H27C | 109.5 |
C20—C12—H12 | 108.1 | C6—O1—C7 | 118.76 (12) |
C8—C12—H12 | 108.1 | C11—O2—C12 | 116.87 (11) |
O4—C13—O3 | 115.93 (13) | C14—O3—C13 | 121.98 (11) |
O4—C13—C10 | 125.67 (14) | C26—O5—C27 | 115.86 (13) |
C6—C1—C2—C3 | 0.0 (3) | O3—C14—C15—C11 | 4.2 (2) |
C1—C2—C3—C4 | −0.3 (3) | C19—C14—C15—C11 | −176.08 (13) |
C2—C3—C4—C5 | 1.1 (3) | O2—C11—C15—C14 | 179.24 (12) |
C3—C4—C5—C6 | −1.6 (2) | C10—C11—C15—C14 | 1.6 (2) |
C3—C4—C5—C9 | −174.77 (15) | O2—C11—C15—C16 | 1.9 (2) |
C4—C5—C6—O1 | −177.19 (14) | C10—C11—C15—C16 | −175.73 (14) |
C9—C5—C6—O1 | −3.9 (2) | C14—C15—C16—C17 | −1.0 (2) |
C4—C5—C6—C1 | 1.4 (2) | C11—C15—C16—C17 | 176.29 (14) |
C9—C5—C6—C1 | 174.64 (14) | C15—C16—C17—C18 | −0.3 (3) |
C2—C1—C6—O1 | 178.06 (15) | C16—C17—C18—C19 | 1.2 (3) |
C2—C1—C6—C5 | −0.6 (2) | C17—C18—C19—C14 | −0.8 (2) |
O1—C7—C8—C26 | 66.18 (16) | O3—C14—C19—C18 | 179.25 (14) |
O1—C7—C8—C9 | −56.20 (16) | C15—C14—C19—C18 | −0.5 (2) |
O1—C7—C8—C12 | −175.67 (12) | O2—C12—C20—C21 | 142.93 (14) |
C6—C5—C9—C10 | 93.17 (16) | C8—C12—C20—C21 | −94.41 (17) |
C4—C5—C9—C10 | −93.83 (17) | O2—C12—C20—C25 | −38.48 (18) |
C6—C5—C9—C8 | −28.10 (18) | C8—C12—C20—C25 | 84.17 (18) |
C4—C5—C9—C8 | 144.90 (14) | C25—C20—C21—C22 | 0.5 (2) |
C7—C8—C9—C10 | −71.67 (14) | C12—C20—C21—C22 | 179.09 (15) |
C26—C8—C9—C10 | 166.90 (11) | C20—C21—C22—C23 | −0.1 (3) |
C12—C8—C9—C10 | 49.16 (14) | C21—C22—C23—C24 | −0.9 (3) |
C7—C8—C9—C5 | 55.38 (15) | C22—C23—C24—C25 | 1.5 (3) |
C26—C8—C9—C5 | −66.05 (14) | C23—C24—C25—C20 | −1.2 (3) |
C12—C8—C9—C5 | 176.21 (11) | C21—C20—C25—C24 | 0.2 (2) |
C5—C9—C10—C11 | −140.03 (14) | C12—C20—C25—C24 | −178.41 (15) |
C8—C9—C10—C11 | −19.34 (17) | C7—C8—C26—O6 | 14.1 (2) |
C5—C9—C10—C13 | 43.55 (18) | C9—C8—C26—O6 | 135.12 (15) |
C8—C9—C10—C13 | 164.25 (12) | C12—C8—C26—O6 | −106.27 (16) |
C13—C10—C11—O2 | 175.09 (12) | C7—C8—C26—O5 | −168.35 (12) |
C9—C10—C11—O2 | −1.4 (2) | C9—C8—C26—O5 | −47.33 (15) |
C13—C10—C11—C15 | −7.5 (2) | C12—C8—C26—O5 | 71.28 (14) |
C9—C10—C11—C15 | 176.06 (12) | C5—C6—O1—C7 | 7.0 (2) |
C7—C8—C12—O2 | 56.60 (15) | C1—C6—O1—C7 | −171.66 (14) |
C26—C8—C12—O2 | 176.37 (11) | C8—C7—O1—C6 | 24.1 (2) |
C9—C8—C12—O2 | −63.21 (14) | C10—C11—O2—C12 | −11.38 (19) |
C7—C8—C12—C20 | −65.08 (16) | C15—C11—O2—C12 | 171.01 (11) |
C26—C8—C12—C20 | 54.69 (16) | C20—C12—O2—C11 | 169.19 (11) |
C9—C8—C12—C20 | 175.12 (12) | C8—C12—O2—C11 | 43.41 (15) |
C11—C10—C13—O4 | −171.57 (14) | C19—C14—O3—C13 | 176.57 (12) |
C9—C10—C13—O4 | 5.0 (2) | C15—C14—O3—C13 | −3.7 (2) |
C11—C10—C13—O3 | 7.88 (19) | O4—C13—O3—C14 | 177.07 (13) |
C9—C10—C13—O3 | −175.57 (11) | C10—C13—O3—C14 | −2.43 (19) |
O3—C14—C15—C16 | −178.36 (13) | O6—C26—O5—C27 | 3.7 (2) |
C19—C14—C15—C16 | 1.4 (2) | C8—C26—O5—C27 | −173.81 (13) |
Cg1 and Cg2 are the centroids of rings C14–C19 and C1–C6, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O4i | 0.93 | 2.58 | 3.411 (2) | 149 |
C27—H27C···O4ii | 0.96 | 2.37 | 3.053 (2) | 128 |
C12—H12···Cg1iii | 0.98 | 2.73 | 3.6861 (17) | 166 |
C18—H18···Cg2iv | 0.93 | 2.84 | 3.674 (2) | 150 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+2, y−1/2, −z+1/2; (iii) −x+2, −y+1, −z; (iv) −x+1, −y+1, −z. |
C24H22O5 | F(000) = 824 |
Mr = 390.42 | Dx = 1.352 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5466 reflections |
a = 11.1694 (10) Å | θ = 2.1–29.8° |
b = 20.1405 (19) Å | µ = 0.09 mm−1 |
c = 8.5835 (7) Å | T = 296 K |
β = 96.453 (3)° | Block, colourless |
V = 1918.7 (3) Å3 | 0.35 × 0.30 × 0.25 mm |
Z = 4 |
Bruker Kappa APEXII CCD diffractometer | 5466 independent reflections |
Radiation source: fine-focus sealed tube | 3694 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ω & φ scans | θmax = 29.8°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −15→15 |
Tmin = 0.968, Tmax = 0.977 | k = −28→27 |
23342 measured reflections | l = −10→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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.155 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0894P)2 + 0.1805P] where P = (Fo2 + 2Fc2)/3 |
5466 reflections | (Δ/σ)max < 0.001 |
263 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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 | ||
C1 | 0.31613 (14) | 0.23586 (8) | 0.65866 (19) | 0.0508 (4) | |
H1 | 0.2975 | 0.2790 | 0.6860 | 0.061* | |
C2 | 0.42353 (15) | 0.20782 (10) | 0.7195 (2) | 0.0593 (4) | |
H2 | 0.4769 | 0.2317 | 0.7894 | 0.071* | |
C3 | 0.45178 (15) | 0.14467 (10) | 0.6769 (2) | 0.0601 (4) | |
H3 | 0.5257 | 0.1262 | 0.7147 | 0.072* | |
C4 | 0.37039 (13) | 0.10856 (8) | 0.57786 (18) | 0.0478 (4) | |
H4 | 0.3898 | 0.0653 | 0.5521 | 0.057* | |
C5 | 0.25975 (11) | 0.13496 (7) | 0.51513 (14) | 0.0348 (3) | |
C6 | 0.23532 (12) | 0.19988 (7) | 0.55629 (16) | 0.0379 (3) | |
C7 | 0.05795 (12) | 0.20179 (7) | 0.37858 (16) | 0.0374 (3) | |
H7A | 0.0956 | 0.2085 | 0.2833 | 0.045* | |
H7B | −0.0206 | 0.2229 | 0.3648 | 0.045* | |
C8 | 0.04229 (11) | 0.12785 (6) | 0.40481 (14) | 0.0311 (3) | |
C9 | 0.16596 (11) | 0.09252 (6) | 0.41771 (14) | 0.0316 (3) | |
H9 | 0.1580 | 0.0510 | 0.4751 | 0.038* | |
C10 | 0.20028 (12) | 0.07429 (7) | 0.25652 (15) | 0.0376 (3) | |
C11 | 0.12973 (14) | 0.08917 (8) | 0.12367 (16) | 0.0436 (3) | |
C12 | −0.03692 (12) | 0.09634 (7) | 0.26444 (15) | 0.0360 (3) | |
H12 | −0.0339 | 0.0480 | 0.2781 | 0.043* | |
C13 | 0.29831 (14) | 0.02678 (8) | 0.2427 (2) | 0.0486 (4) | |
C14 | 0.33358 (18) | 0.01282 (12) | 0.0817 (2) | 0.0733 (6) | |
H14A | 0.4203 | 0.0074 | 0.0892 | 0.088* | |
H14B | 0.2971 | −0.0288 | 0.0442 | 0.088* | |
C15 | 0.29703 (19) | 0.06569 (12) | −0.0346 (2) | 0.0751 (6) | |
H15A | 0.3138 | 0.0513 | −0.1378 | 0.090* | |
H15B | 0.3437 | 0.1055 | −0.0077 | 0.090* | |
C16 | 0.16417 (17) | 0.08128 (11) | −0.03816 (19) | 0.0652 (5) | |
H16A | 0.1460 | 0.1219 | −0.0968 | 0.078* | |
H16B | 0.1173 | 0.0457 | −0.0911 | 0.078* | |
C17 | −0.16701 (13) | 0.11648 (7) | 0.23894 (16) | 0.0418 (3) | |
C18 | −0.20700 (17) | 0.16855 (9) | 0.1421 (2) | 0.0578 (4) | |
H18 | −0.1527 | 0.1939 | 0.0927 | 0.069* | |
C19 | −0.3299 (2) | 0.18263 (11) | 0.1194 (3) | 0.0842 (7) | |
H19 | −0.3580 | 0.2171 | 0.0530 | 0.101* | |
C20 | −0.40961 (19) | 0.14608 (13) | 0.1939 (4) | 0.0922 (8) | |
H20 | −0.4914 | 0.1560 | 0.1778 | 0.111* | |
C21 | −0.37047 (17) | 0.09518 (12) | 0.2915 (3) | 0.0804 (6) | |
H21 | −0.4249 | 0.0709 | 0.3432 | 0.096* | |
C22 | −0.24989 (14) | 0.08015 (9) | 0.3127 (2) | 0.0560 (4) | |
H22 | −0.2232 | 0.0450 | 0.3778 | 0.067* | |
C23 | −0.01905 (11) | 0.11340 (6) | 0.55155 (15) | 0.0326 (3) | |
C24 | −0.16103 (16) | 0.14882 (9) | 0.7159 (2) | 0.0607 (5) | |
H24A | −0.2197 | 0.1152 | 0.6843 | 0.091* | |
H24B | −0.2013 | 0.1887 | 0.7425 | 0.091* | |
H24C | −0.1091 | 0.1336 | 0.8055 | 0.091* | |
O1 | 0.12981 (9) | 0.23212 (5) | 0.50640 (12) | 0.0447 (3) | |
O2 | 0.01594 (10) | 0.11195 (6) | 0.12316 (11) | 0.0471 (3) | |
O3 | 0.34448 (11) | −0.00487 (7) | 0.35498 (15) | 0.0625 (3) | |
O4 | −0.00799 (10) | 0.06241 (5) | 0.62305 (12) | 0.0489 (3) | |
O5 | −0.09014 (9) | 0.16233 (5) | 0.58848 (12) | 0.0466 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0511 (9) | 0.0473 (9) | 0.0540 (9) | −0.0135 (7) | 0.0058 (7) | −0.0108 (7) |
C2 | 0.0479 (9) | 0.0697 (12) | 0.0575 (10) | −0.0193 (8) | −0.0071 (7) | −0.0041 (8) |
C3 | 0.0403 (8) | 0.0725 (12) | 0.0642 (11) | −0.0054 (8) | −0.0084 (7) | 0.0036 (9) |
C4 | 0.0381 (7) | 0.0530 (9) | 0.0513 (9) | 0.0026 (6) | −0.0001 (6) | −0.0004 (7) |
C5 | 0.0338 (6) | 0.0405 (7) | 0.0303 (6) | −0.0017 (5) | 0.0050 (5) | 0.0011 (5) |
C6 | 0.0361 (6) | 0.0402 (7) | 0.0383 (7) | −0.0044 (6) | 0.0073 (5) | −0.0010 (5) |
C7 | 0.0396 (7) | 0.0326 (7) | 0.0395 (7) | 0.0011 (5) | 0.0027 (5) | 0.0026 (5) |
C8 | 0.0317 (6) | 0.0307 (6) | 0.0305 (6) | 0.0009 (5) | 0.0025 (4) | 0.0004 (5) |
C9 | 0.0313 (6) | 0.0316 (6) | 0.0321 (6) | 0.0024 (5) | 0.0042 (5) | 0.0006 (5) |
C10 | 0.0394 (7) | 0.0379 (7) | 0.0368 (7) | −0.0015 (5) | 0.0093 (5) | −0.0062 (5) |
C11 | 0.0485 (8) | 0.0467 (8) | 0.0363 (7) | −0.0030 (6) | 0.0082 (6) | −0.0066 (6) |
C12 | 0.0384 (7) | 0.0362 (7) | 0.0323 (6) | 0.0013 (5) | −0.0008 (5) | −0.0007 (5) |
C13 | 0.0414 (8) | 0.0502 (9) | 0.0558 (9) | 0.0002 (7) | 0.0134 (7) | −0.0153 (7) |
C14 | 0.0639 (11) | 0.0924 (15) | 0.0681 (12) | 0.0066 (11) | 0.0268 (9) | −0.0283 (11) |
C15 | 0.0785 (13) | 0.0995 (16) | 0.0534 (11) | −0.0132 (12) | 0.0334 (9) | −0.0195 (11) |
C16 | 0.0760 (12) | 0.0876 (14) | 0.0339 (8) | −0.0055 (10) | 0.0145 (8) | −0.0095 (8) |
C17 | 0.0397 (7) | 0.0412 (8) | 0.0416 (7) | 0.0045 (6) | −0.0079 (6) | −0.0072 (6) |
C18 | 0.0592 (10) | 0.0520 (10) | 0.0576 (10) | 0.0109 (8) | −0.0144 (8) | −0.0001 (7) |
C19 | 0.0760 (14) | 0.0629 (13) | 0.1027 (17) | 0.0275 (11) | −0.0389 (13) | −0.0101 (11) |
C20 | 0.0431 (10) | 0.0777 (16) | 0.148 (2) | 0.0128 (10) | −0.0234 (13) | −0.0324 (16) |
C21 | 0.0398 (9) | 0.0790 (15) | 0.1203 (18) | −0.0055 (9) | 0.0004 (11) | −0.0154 (13) |
C22 | 0.0415 (8) | 0.0573 (10) | 0.0675 (11) | −0.0033 (7) | −0.0016 (7) | −0.0020 (8) |
C23 | 0.0316 (6) | 0.0338 (6) | 0.0323 (6) | −0.0011 (5) | 0.0027 (5) | −0.0029 (5) |
C24 | 0.0606 (10) | 0.0591 (10) | 0.0691 (11) | 0.0022 (8) | 0.0366 (9) | −0.0021 (8) |
O1 | 0.0432 (5) | 0.0339 (5) | 0.0560 (6) | −0.0005 (4) | 0.0013 (4) | −0.0096 (4) |
O2 | 0.0518 (6) | 0.0586 (7) | 0.0300 (5) | 0.0053 (5) | 0.0010 (4) | 0.0005 (4) |
O3 | 0.0557 (7) | 0.0606 (8) | 0.0711 (8) | 0.0213 (6) | 0.0069 (6) | −0.0092 (6) |
O4 | 0.0620 (7) | 0.0429 (6) | 0.0442 (6) | 0.0077 (5) | 0.0161 (5) | 0.0094 (4) |
O5 | 0.0472 (6) | 0.0415 (6) | 0.0549 (6) | 0.0055 (4) | 0.0223 (5) | 0.0020 (4) |
C1—C2 | 1.375 (2) | C13—O3 | 1.220 (2) |
C1—C6 | 1.391 (2) | C13—C14 | 1.506 (2) |
C1—H1 | 0.9300 | C14—C15 | 1.485 (3) |
C2—C3 | 1.370 (3) | C14—H14A | 0.9700 |
C2—H2 | 0.9300 | C14—H14B | 0.9700 |
C3—C4 | 1.380 (2) | C15—C16 | 1.514 (3) |
C3—H3 | 0.9300 | C15—H15A | 0.9700 |
C4—C5 | 1.3965 (19) | C15—H15B | 0.9700 |
C4—H4 | 0.9300 | C16—H16A | 0.9700 |
C5—C6 | 1.389 (2) | C16—H16B | 0.9700 |
C5—C9 | 1.5265 (18) | C17—C18 | 1.381 (2) |
C6—O1 | 1.3712 (17) | C17—C22 | 1.388 (2) |
C7—O1 | 1.4224 (16) | C18—C19 | 1.394 (3) |
C7—C8 | 1.5190 (18) | C18—H18 | 0.9300 |
C7—H7A | 0.9700 | C19—C20 | 1.368 (4) |
C7—H7B | 0.9700 | C19—H19 | 0.9300 |
C8—C23 | 1.5280 (17) | C20—C21 | 1.365 (4) |
C8—C9 | 1.5467 (17) | C20—H20 | 0.9300 |
C8—C12 | 1.5484 (18) | C21—C22 | 1.372 (2) |
C9—C10 | 1.5216 (17) | C21—H21 | 0.9300 |
C9—H9 | 0.9800 | C22—H22 | 0.9300 |
C10—C11 | 1.345 (2) | C23—O4 | 1.1957 (16) |
C10—C13 | 1.469 (2) | C23—O5 | 1.3262 (15) |
C11—O2 | 1.3508 (18) | C24—O5 | 1.4465 (17) |
C11—C16 | 1.491 (2) | C24—H24A | 0.9600 |
C12—O2 | 1.4418 (16) | C24—H24B | 0.9600 |
C12—C17 | 1.5008 (19) | C24—H24C | 0.9600 |
C12—H12 | 0.9800 | ||
C2—C1—C6 | 120.18 (16) | C10—C13—C14 | 118.02 (16) |
C2—C1—H1 | 119.9 | C15—C14—C13 | 113.74 (16) |
C6—C1—H1 | 119.9 | C15—C14—H14A | 108.8 |
C3—C2—C1 | 119.83 (15) | C13—C14—H14A | 108.8 |
C3—C2—H2 | 120.1 | C15—C14—H14B | 108.8 |
C1—C2—H2 | 120.1 | C13—C14—H14B | 108.8 |
C2—C3—C4 | 119.87 (16) | H14A—C14—H14B | 107.7 |
C2—C3—H3 | 120.1 | C14—C15—C16 | 110.94 (16) |
C4—C3—H3 | 120.1 | C14—C15—H15A | 109.5 |
C3—C4—C5 | 122.02 (16) | C16—C15—H15A | 109.5 |
C3—C4—H4 | 119.0 | C14—C15—H15B | 109.5 |
C5—C4—H4 | 119.0 | C16—C15—H15B | 109.5 |
C6—C5—C4 | 116.79 (13) | H15A—C15—H15B | 108.0 |
C6—C5—C9 | 121.60 (11) | C11—C16—C15 | 110.98 (15) |
C4—C5—C9 | 121.41 (13) | C11—C16—H16A | 109.4 |
O1—C6—C5 | 123.54 (12) | C15—C16—H16A | 109.4 |
O1—C6—C1 | 115.13 (13) | C11—C16—H16B | 109.4 |
C5—C6—C1 | 121.26 (14) | C15—C16—H16B | 109.4 |
O1—C7—C8 | 111.79 (11) | H16A—C16—H16B | 108.0 |
O1—C7—H7A | 109.3 | C18—C17—C22 | 119.22 (15) |
C8—C7—H7A | 109.3 | C18—C17—C12 | 122.37 (15) |
O1—C7—H7B | 109.3 | C22—C17—C12 | 118.39 (13) |
C8—C7—H7B | 109.3 | C17—C18—C19 | 119.0 (2) |
H7A—C7—H7B | 107.9 | C17—C18—H18 | 120.5 |
C7—C8—C23 | 112.26 (10) | C19—C18—H18 | 120.5 |
C7—C8—C9 | 110.17 (10) | C20—C19—C18 | 120.5 (2) |
C23—C8—C9 | 109.45 (10) | C20—C19—H19 | 119.8 |
C7—C8—C12 | 110.59 (10) | C18—C19—H19 | 119.8 |
C23—C8—C12 | 107.06 (10) | C21—C20—C19 | 120.75 (19) |
C9—C8—C12 | 107.14 (10) | C21—C20—H20 | 119.6 |
C10—C9—C5 | 113.94 (10) | C19—C20—H20 | 119.6 |
C10—C9—C8 | 111.11 (10) | C20—C21—C22 | 119.3 (2) |
C5—C9—C8 | 109.51 (10) | C20—C21—H21 | 120.4 |
C10—C9—H9 | 107.3 | C22—C21—H21 | 120.4 |
C5—C9—H9 | 107.3 | C21—C22—C17 | 121.21 (19) |
C8—C9—H9 | 107.3 | C21—C22—H22 | 119.4 |
C11—C10—C13 | 116.61 (12) | C17—C22—H22 | 119.4 |
C11—C10—C9 | 122.25 (12) | O4—C23—O5 | 123.07 (12) |
C13—C10—C9 | 119.78 (12) | O4—C23—C8 | 123.83 (11) |
C10—C11—O2 | 122.67 (12) | O5—C23—C8 | 113.04 (11) |
C10—C11—C16 | 125.32 (15) | O5—C24—H24A | 109.5 |
O2—C11—C16 | 111.99 (13) | O5—C24—H24B | 109.5 |
O2—C12—C17 | 107.44 (11) | H24A—C24—H24B | 109.5 |
O2—C12—C8 | 108.24 (10) | O5—C24—H24C | 109.5 |
C17—C12—C8 | 117.51 (11) | H24A—C24—H24C | 109.5 |
O2—C12—H12 | 107.8 | H24B—C24—H24C | 109.5 |
C17—C12—H12 | 107.8 | C6—O1—C7 | 115.35 (10) |
C8—C12—H12 | 107.8 | C11—O2—C12 | 113.41 (10) |
O3—C13—C10 | 121.98 (14) | C23—O5—C24 | 115.74 (12) |
O3—C13—C14 | 119.76 (15) | ||
C6—C1—C2—C3 | 1.1 (3) | C11—C10—C13—O3 | −158.15 (16) |
C1—C2—C3—C4 | −2.5 (3) | C9—C10—C13—O3 | 8.8 (2) |
C2—C3—C4—C5 | 1.7 (3) | C11—C10—C13—C14 | 16.1 (2) |
C3—C4—C5—C6 | 0.4 (2) | C9—C10—C13—C14 | −176.91 (14) |
C3—C4—C5—C9 | −174.44 (14) | O3—C13—C14—C15 | −164.40 (17) |
C4—C5—C6—O1 | −178.79 (12) | C10—C13—C14—C15 | 21.2 (2) |
C9—C5—C6—O1 | −3.93 (19) | C13—C14—C15—C16 | −52.5 (2) |
C4—C5—C6—C1 | −1.78 (19) | C10—C11—C16—C15 | −10.0 (3) |
C9—C5—C6—C1 | 173.08 (12) | O2—C11—C16—C15 | 171.53 (16) |
C2—C1—C6—O1 | 178.29 (13) | C14—C15—C16—C11 | 46.8 (2) |
C2—C1—C6—C5 | 1.0 (2) | O2—C12—C17—C18 | −30.11 (18) |
O1—C7—C8—C23 | 60.13 (14) | C8—C12—C17—C18 | 92.13 (16) |
O1—C7—C8—C9 | −62.12 (13) | O2—C12—C17—C22 | 148.25 (13) |
O1—C7—C8—C12 | 179.62 (10) | C8—C12—C17—C22 | −89.51 (17) |
C6—C5—C9—C10 | 114.47 (13) | C22—C17—C18—C19 | −0.9 (2) |
C4—C5—C9—C10 | −70.91 (16) | C12—C17—C18—C19 | 177.47 (16) |
C6—C5—C9—C8 | −10.65 (16) | C17—C18—C19—C20 | 1.0 (3) |
C4—C5—C9—C8 | 163.97 (12) | C18—C19—C20—C21 | −0.1 (4) |
C7—C8—C9—C10 | −85.59 (13) | C19—C20—C21—C22 | −1.0 (4) |
C23—C8—C9—C10 | 150.52 (11) | C20—C21—C22—C17 | 1.2 (3) |
C12—C8—C9—C10 | 34.77 (14) | C18—C17—C22—C21 | −0.2 (3) |
C7—C8—C9—C5 | 41.15 (13) | C12—C17—C22—C21 | −178.62 (16) |
C23—C8—C9—C5 | −82.74 (12) | C7—C8—C23—O4 | −155.62 (13) |
C12—C8—C9—C5 | 161.51 (10) | C9—C8—C23—O4 | −32.96 (17) |
C5—C9—C10—C11 | −123.25 (14) | C12—C8—C23—O4 | 82.84 (15) |
C8—C9—C10—C11 | 1.02 (18) | C7—C8—C23—O5 | 26.93 (15) |
C5—C9—C10—C13 | 70.53 (16) | C9—C8—C23—O5 | 149.59 (11) |
C8—C9—C10—C13 | −165.20 (12) | C12—C8—C23—O5 | −94.61 (12) |
C13—C10—C11—O2 | 156.24 (14) | C5—C6—O1—C7 | −15.15 (18) |
C9—C10—C11—O2 | −10.4 (2) | C1—C6—O1—C7 | 167.68 (12) |
C13—C10—C11—C16 | −22.1 (2) | C8—C7—O1—C6 | 48.13 (15) |
C9—C10—C11—C16 | 171.31 (15) | C10—C11—O2—C12 | −21.3 (2) |
C7—C8—C12—O2 | 54.74 (13) | C16—C11—O2—C12 | 157.21 (13) |
C23—C8—C12—O2 | 177.32 (10) | C17—C12—O2—C11 | −172.70 (12) |
C9—C8—C12—O2 | −65.35 (13) | C8—C12—O2—C11 | 59.47 (14) |
C7—C8—C12—C17 | −67.09 (15) | O4—C23—O5—C24 | −4.0 (2) |
C23—C8—C12—C17 | 55.49 (15) | C8—C23—O5—C24 | 173.49 (12) |
C9—C8—C12—C17 | 172.82 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O3 | 0.93 | 2.22 | 2.973 (2) | 138 |
C12—H12···O4i | 0.98 | 2.41 | 3.3613 (18) | 164 |
Symmetry code: (i) −x, −y, −z+1. |
C25H23N3O4 | F(000) = 904 |
Mr = 429.46 | Dx = 1.345 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3715 reflections |
a = 11.4471 (5) Å | θ = 2.1–25.0° |
b = 11.2076 (4) Å | µ = 0.09 mm−1 |
c = 16.5407 (7) Å | T = 296 K |
β = 91.990 (2)° | Block, colourless |
V = 2120.80 (15) Å3 | 0.35 × 0.30 × 0.25 mm |
Z = 4 |
Bruker Kappa APEXII CCD diffractometer | 3715 independent reflections |
Radiation source: fine-focus sealed tube | 2814 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ω & φ scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −13→13 |
Tmin = 0.968, Tmax = 0.977 | k = −10→13 |
18281 measured reflections | l = −19→19 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0576P)2 + 0.8627P] where P = (Fo2 + 2Fc2)/3 |
3715 reflections | (Δ/σ)max = 0.007 |
292 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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 | ||
C1 | 0.1534 (2) | −0.1733 (2) | 0.02179 (14) | 0.0590 (6) | |
H1 | 0.1589 | −0.1965 | −0.0319 | 0.071* | |
C2 | 0.0885 (2) | −0.2402 (2) | 0.07377 (15) | 0.0609 (6) | |
H2 | 0.0507 | −0.3091 | 0.0555 | 0.073* | |
C3 | 0.0802 (2) | −0.2042 (2) | 0.15302 (15) | 0.0565 (6) | |
H3 | 0.0371 | −0.2493 | 0.1886 | 0.068* | |
C4 | 0.13542 (17) | −0.10173 (18) | 0.17962 (13) | 0.0465 (5) | |
H4 | 0.1289 | −0.0786 | 0.2333 | 0.056* | |
C5 | 0.20076 (16) | −0.03175 (17) | 0.12840 (11) | 0.0396 (4) | |
C6 | 0.21040 (18) | −0.07139 (18) | 0.04949 (12) | 0.0468 (5) | |
C7 | 0.35811 (18) | 0.06931 (19) | 0.02593 (12) | 0.0468 (5) | |
H7A | 0.3918 | 0.1143 | −0.0176 | 0.056* | |
H7B | 0.4205 | 0.0255 | 0.0538 | 0.056* | |
C8 | 0.30204 (16) | 0.15565 (17) | 0.08532 (11) | 0.0373 (4) | |
C9 | 0.25965 (16) | 0.08300 (17) | 0.15816 (11) | 0.0372 (4) | |
H9 | 0.3287 | 0.0606 | 0.1915 | 0.045* | |
C10 | 0.18416 (15) | 0.16192 (16) | 0.20870 (11) | 0.0359 (4) | |
C11 | 0.13384 (15) | 0.26105 (17) | 0.17771 (10) | 0.0353 (4) | |
C12 | 0.19681 (16) | 0.22106 (17) | 0.04440 (11) | 0.0374 (4) | |
H12 | 0.1394 | 0.1608 | 0.0267 | 0.045* | |
C13 | 0.17301 (16) | 0.13736 (17) | 0.29330 (11) | 0.0391 (4) | |
C14 | 0.04976 (16) | 0.31618 (18) | 0.30307 (12) | 0.0409 (5) | |
C15 | 0.01236 (19) | 0.44176 (19) | 0.18395 (13) | 0.0522 (5) | |
H15A | 0.0704 | 0.4894 | 0.1586 | 0.078* | |
H15B | −0.0251 | 0.4883 | 0.2243 | 0.078* | |
H15C | −0.0449 | 0.4159 | 0.1439 | 0.078* | |
C16 | 0.0767 (2) | 0.1869 (2) | 0.41949 (12) | 0.0571 (6) | |
H16A | 0.1301 | 0.2304 | 0.4545 | 0.086* | |
H16B | 0.0866 | 0.1029 | 0.4287 | 0.086* | |
H16C | −0.0021 | 0.2094 | 0.4306 | 0.086* | |
C17 | 0.22490 (16) | 0.29571 (17) | −0.02756 (11) | 0.0378 (4) | |
C18 | 0.2163 (2) | 0.24542 (19) | −0.10328 (12) | 0.0496 (5) | |
H18 | 0.1908 | 0.1670 | −0.1091 | 0.059* | |
C19 | 0.2453 (2) | 0.31004 (19) | −0.17082 (12) | 0.0556 (6) | |
H19 | 0.2390 | 0.2742 | −0.2215 | 0.067* | |
C20 | 0.28318 (19) | 0.42640 (18) | −0.16474 (12) | 0.0474 (5) | |
C21 | 0.29008 (19) | 0.47620 (18) | −0.08850 (12) | 0.0490 (5) | |
H21 | 0.3152 | 0.5548 | −0.0828 | 0.059* | |
C22 | 0.26093 (18) | 0.41312 (17) | −0.02041 (12) | 0.0443 (5) | |
H22 | 0.2655 | 0.4495 | 0.0301 | 0.053* | |
C23 | 0.3174 (3) | 0.4970 (2) | −0.23790 (14) | 0.0722 (7) | |
H23A | 0.2502 | 0.5435 | −0.2564 | 0.087* | |
H23B | 0.3782 | 0.5528 | −0.2210 | 0.087* | |
C24 | 0.3588 (3) | 0.4293 (3) | −0.30635 (16) | 0.0839 (9) | |
H24A | 0.4161 | 0.3723 | −0.2876 | 0.126* | |
H24B | 0.3932 | 0.4827 | −0.3441 | 0.126* | |
H24C | 0.2942 | 0.3882 | −0.3325 | 0.126* | |
C25 | 0.39321 (18) | 0.24049 (19) | 0.11184 (12) | 0.0438 (5) | |
N1 | 0.10034 (14) | 0.21462 (15) | 0.33494 (9) | 0.0413 (4) | |
N2 | 0.06822 (13) | 0.33754 (14) | 0.22202 (9) | 0.0395 (4) | |
N3 | 0.46792 (18) | 0.3023 (2) | 0.13123 (13) | 0.0693 (6) | |
O1 | 0.27450 (14) | −0.01194 (13) | −0.00673 (8) | 0.0555 (4) | |
O2 | 0.14164 (11) | 0.29896 (11) | 0.10132 (7) | 0.0415 (3) | |
O3 | 0.22107 (12) | 0.05425 (13) | 0.32899 (8) | 0.0499 (4) | |
O4 | −0.00801 (13) | 0.38384 (13) | 0.34285 (9) | 0.0544 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0813 (16) | 0.0442 (13) | 0.0515 (13) | −0.0007 (12) | 0.0011 (12) | −0.0045 (10) |
C2 | 0.0706 (15) | 0.0425 (13) | 0.0691 (16) | −0.0078 (11) | −0.0053 (12) | 0.0015 (12) |
C3 | 0.0590 (13) | 0.0445 (13) | 0.0664 (15) | −0.0057 (10) | 0.0076 (11) | 0.0091 (11) |
C4 | 0.0524 (12) | 0.0405 (12) | 0.0470 (11) | 0.0016 (9) | 0.0088 (9) | 0.0058 (9) |
C5 | 0.0433 (10) | 0.0358 (11) | 0.0400 (10) | 0.0066 (8) | 0.0066 (8) | 0.0037 (8) |
C6 | 0.0596 (12) | 0.0367 (11) | 0.0445 (11) | 0.0040 (9) | 0.0084 (10) | 0.0039 (9) |
C7 | 0.0562 (12) | 0.0425 (12) | 0.0427 (11) | 0.0034 (10) | 0.0172 (9) | 0.0018 (9) |
C8 | 0.0407 (10) | 0.0363 (11) | 0.0355 (10) | 0.0006 (8) | 0.0098 (8) | 0.0019 (8) |
C9 | 0.0405 (10) | 0.0375 (11) | 0.0341 (10) | 0.0034 (8) | 0.0081 (8) | 0.0045 (8) |
C10 | 0.0392 (9) | 0.0361 (10) | 0.0330 (9) | −0.0017 (8) | 0.0097 (8) | 0.0006 (8) |
C11 | 0.0349 (9) | 0.0385 (11) | 0.0330 (9) | −0.0036 (8) | 0.0081 (7) | 0.0006 (8) |
C12 | 0.0437 (10) | 0.0361 (11) | 0.0327 (9) | −0.0012 (8) | 0.0086 (8) | 0.0012 (8) |
C13 | 0.0394 (10) | 0.0402 (11) | 0.0382 (10) | −0.0040 (9) | 0.0080 (8) | 0.0015 (9) |
C14 | 0.0388 (10) | 0.0436 (12) | 0.0411 (11) | −0.0063 (9) | 0.0114 (8) | −0.0045 (9) |
C15 | 0.0535 (12) | 0.0487 (13) | 0.0550 (13) | 0.0134 (10) | 0.0117 (10) | 0.0039 (10) |
C16 | 0.0685 (14) | 0.0674 (16) | 0.0364 (11) | −0.0008 (12) | 0.0178 (10) | 0.0042 (10) |
C17 | 0.0424 (10) | 0.0369 (11) | 0.0343 (10) | −0.0020 (8) | 0.0051 (8) | 0.0026 (8) |
C18 | 0.0733 (14) | 0.0363 (11) | 0.0394 (11) | −0.0115 (10) | 0.0070 (10) | −0.0011 (9) |
C19 | 0.0886 (17) | 0.0463 (13) | 0.0323 (10) | −0.0067 (12) | 0.0100 (10) | −0.0031 (9) |
C20 | 0.0643 (13) | 0.0396 (12) | 0.0391 (11) | −0.0005 (10) | 0.0109 (9) | 0.0050 (9) |
C21 | 0.0699 (14) | 0.0332 (11) | 0.0443 (11) | −0.0060 (10) | 0.0062 (10) | 0.0022 (9) |
C22 | 0.0610 (12) | 0.0363 (11) | 0.0359 (10) | −0.0038 (9) | 0.0050 (9) | −0.0010 (8) |
C23 | 0.114 (2) | 0.0560 (15) | 0.0477 (13) | −0.0055 (14) | 0.0223 (14) | 0.0121 (12) |
C24 | 0.116 (2) | 0.0790 (19) | 0.0596 (16) | 0.0160 (17) | 0.0368 (15) | 0.0218 (14) |
C25 | 0.0440 (11) | 0.0488 (12) | 0.0392 (10) | 0.0005 (10) | 0.0107 (9) | 0.0037 (9) |
N1 | 0.0469 (9) | 0.0451 (10) | 0.0326 (8) | −0.0020 (8) | 0.0118 (7) | 0.0003 (7) |
N2 | 0.0408 (8) | 0.0376 (9) | 0.0409 (9) | 0.0034 (7) | 0.0110 (7) | 0.0004 (7) |
N3 | 0.0617 (12) | 0.0812 (15) | 0.0654 (13) | −0.0214 (12) | 0.0054 (10) | −0.0054 (11) |
O1 | 0.0826 (11) | 0.0449 (9) | 0.0402 (8) | −0.0055 (8) | 0.0187 (7) | −0.0042 (7) |
O2 | 0.0500 (8) | 0.0403 (8) | 0.0349 (7) | 0.0083 (6) | 0.0118 (6) | 0.0060 (6) |
O3 | 0.0603 (9) | 0.0507 (9) | 0.0390 (7) | 0.0067 (7) | 0.0071 (6) | 0.0089 (7) |
O4 | 0.0604 (9) | 0.0524 (9) | 0.0518 (9) | 0.0056 (7) | 0.0219 (7) | −0.0091 (7) |
C1—C2 | 1.378 (3) | C14—O4 | 1.215 (2) |
C1—C6 | 1.385 (3) | C14—N1 | 1.374 (3) |
C1—H1 | 0.9300 | C14—N2 | 1.385 (2) |
C2—C3 | 1.378 (3) | C15—N2 | 1.463 (3) |
C2—H2 | 0.9300 | C15—H15A | 0.9600 |
C3—C4 | 1.376 (3) | C15—H15B | 0.9600 |
C3—H3 | 0.9300 | C15—H15C | 0.9600 |
C4—C5 | 1.392 (3) | C16—N1 | 1.467 (2) |
C4—H4 | 0.9300 | C16—H16A | 0.9600 |
C5—C6 | 1.387 (3) | C16—H16B | 0.9600 |
C5—C9 | 1.526 (3) | C16—H16C | 0.9600 |
C6—O1 | 1.376 (2) | C17—C18 | 1.374 (3) |
C7—O1 | 1.415 (2) | C17—C22 | 1.383 (3) |
C7—C8 | 1.535 (3) | C18—C19 | 1.381 (3) |
C7—H7A | 0.9700 | C18—H18 | 0.9300 |
C7—H7B | 0.9700 | C19—C20 | 1.377 (3) |
C8—C25 | 1.468 (3) | C19—H19 | 0.9300 |
C8—C12 | 1.546 (3) | C20—C21 | 1.379 (3) |
C8—C9 | 1.546 (2) | C20—C23 | 1.508 (3) |
C9—C10 | 1.509 (2) | C21—C22 | 1.381 (3) |
C9—H9 | 0.9800 | C21—H21 | 0.9300 |
C10—C11 | 1.345 (3) | C22—H22 | 0.9300 |
C10—C13 | 1.436 (3) | C23—C24 | 1.456 (3) |
C11—O2 | 1.339 (2) | C23—H23A | 0.9700 |
C11—N2 | 1.369 (2) | C23—H23B | 0.9700 |
C12—O2 | 1.445 (2) | C24—H24A | 0.9600 |
C12—C17 | 1.499 (2) | C24—H24B | 0.9600 |
C12—H12 | 0.9800 | C24—H24C | 0.9600 |
C13—O3 | 1.223 (2) | C25—N3 | 1.138 (3) |
C13—N1 | 1.399 (2) | ||
C2—C1—C6 | 120.0 (2) | N1—C14—N2 | 115.99 (16) |
C2—C1—H1 | 120.0 | N2—C15—H15A | 109.5 |
C6—C1—H1 | 120.0 | N2—C15—H15B | 109.5 |
C1—C2—C3 | 119.4 (2) | H15A—C15—H15B | 109.5 |
C1—C2—H2 | 120.3 | N2—C15—H15C | 109.5 |
C3—C2—H2 | 120.3 | H15A—C15—H15C | 109.5 |
C4—C3—C2 | 120.1 (2) | H15B—C15—H15C | 109.5 |
C4—C3—H3 | 119.9 | N1—C16—H16A | 109.5 |
C2—C3—H3 | 119.9 | N1—C16—H16B | 109.5 |
C3—C4—C5 | 121.8 (2) | H16A—C16—H16B | 109.5 |
C3—C4—H4 | 119.1 | N1—C16—H16C | 109.5 |
C5—C4—H4 | 119.1 | H16A—C16—H16C | 109.5 |
C6—C5—C4 | 117.03 (18) | H16B—C16—H16C | 109.5 |
C6—C5—C9 | 121.66 (17) | C18—C17—C22 | 118.68 (17) |
C4—C5—C9 | 121.31 (17) | C18—C17—C12 | 118.97 (17) |
O1—C6—C1 | 115.57 (19) | C22—C17—C12 | 122.33 (17) |
O1—C6—C5 | 122.86 (18) | C17—C18—C19 | 120.71 (19) |
C1—C6—C5 | 121.6 (2) | C17—C18—H18 | 119.6 |
O1—C7—C8 | 110.96 (16) | C19—C18—H18 | 119.6 |
O1—C7—H7A | 109.4 | C20—C19—C18 | 121.42 (19) |
C8—C7—H7A | 109.4 | C20—C19—H19 | 119.3 |
O1—C7—H7B | 109.4 | C18—C19—H19 | 119.3 |
C8—C7—H7B | 109.4 | C19—C20—C21 | 117.26 (18) |
H7A—C7—H7B | 108.0 | C19—C20—C23 | 121.85 (19) |
C25—C8—C7 | 106.91 (15) | C21—C20—C23 | 120.9 (2) |
C25—C8—C12 | 111.03 (16) | C20—C21—C22 | 122.08 (19) |
C7—C8—C12 | 110.82 (15) | C20—C21—H21 | 119.0 |
C25—C8—C9 | 110.33 (15) | C22—C21—H21 | 119.0 |
C7—C8—C9 | 108.43 (16) | C21—C22—C17 | 119.83 (18) |
C12—C8—C9 | 109.27 (14) | C21—C22—H22 | 120.1 |
C10—C9—C5 | 114.68 (15) | C17—C22—H22 | 120.1 |
C10—C9—C8 | 108.92 (15) | C24—C23—C20 | 116.8 (2) |
C5—C9—C8 | 109.86 (15) | C24—C23—H23A | 108.1 |
C10—C9—H9 | 107.7 | C20—C23—H23A | 108.1 |
C5—C9—H9 | 107.7 | C24—C23—H23B | 108.1 |
C8—C9—H9 | 107.7 | C20—C23—H23B | 108.1 |
C11—C10—C13 | 118.58 (17) | H23A—C23—H23B | 107.3 |
C11—C10—C9 | 121.25 (16) | C23—C24—H24A | 109.5 |
C13—C10—C9 | 119.96 (16) | C23—C24—H24B | 109.5 |
O2—C11—C10 | 125.46 (16) | H24A—C24—H24B | 109.5 |
O2—C11—N2 | 111.24 (16) | C23—C24—H24C | 109.5 |
C10—C11—N2 | 123.29 (16) | H24A—C24—H24C | 109.5 |
O2—C12—C17 | 106.90 (14) | H24B—C24—H24C | 109.5 |
O2—C12—C8 | 110.65 (14) | N3—C25—C8 | 176.6 (2) |
C17—C12—C8 | 115.27 (15) | C14—N1—C13 | 125.03 (16) |
O2—C12—H12 | 107.9 | C14—N1—C16 | 116.85 (16) |
C17—C12—H12 | 107.9 | C13—N1—C16 | 118.12 (17) |
C8—C12—H12 | 107.9 | C11—N2—C14 | 120.98 (16) |
O3—C13—N1 | 119.93 (17) | C11—N2—C15 | 120.60 (16) |
O3—C13—C10 | 124.23 (17) | C14—N2—C15 | 118.38 (16) |
N1—C13—C10 | 115.83 (17) | C6—O1—C7 | 115.02 (15) |
O4—C14—N1 | 122.65 (18) | C11—O2—C12 | 117.91 (14) |
O4—C14—N2 | 121.36 (19) | ||
C6—C1—C2—C3 | 0.6 (4) | C9—C10—C13—N1 | −179.40 (15) |
C1—C2—C3—C4 | 0.6 (3) | O2—C12—C17—C18 | −144.56 (18) |
C2—C3—C4—C5 | −0.1 (3) | C8—C12—C17—C18 | 92.0 (2) |
C3—C4—C5—C6 | −1.6 (3) | O2—C12—C17—C22 | 36.5 (2) |
C3—C4—C5—C9 | 178.79 (18) | C8—C12—C17—C22 | −87.0 (2) |
C2—C1—C6—O1 | 178.9 (2) | C22—C17—C18—C19 | 1.2 (3) |
C2—C1—C6—C5 | −2.3 (3) | C12—C17—C18—C19 | −177.8 (2) |
C4—C5—C6—O1 | −178.57 (18) | C17—C18—C19—C20 | −0.2 (4) |
C9—C5—C6—O1 | 1.1 (3) | C18—C19—C20—C21 | −0.6 (3) |
C4—C5—C6—C1 | 2.8 (3) | C18—C19—C20—C23 | 178.7 (2) |
C9—C5—C6—C1 | −177.61 (19) | C19—C20—C21—C22 | 0.2 (3) |
O1—C7—C8—C25 | −176.52 (15) | C23—C20—C21—C22 | −179.1 (2) |
O1—C7—C8—C12 | −55.4 (2) | C20—C21—C22—C17 | 0.8 (3) |
O1—C7—C8—C9 | 64.5 (2) | C18—C17—C22—C21 | −1.5 (3) |
C6—C5—C9—C10 | 135.93 (18) | C12—C17—C22—C21 | 177.45 (18) |
C4—C5—C9—C10 | −44.5 (2) | C19—C20—C23—C24 | −26.5 (4) |
C6—C5—C9—C8 | 12.9 (2) | C21—C20—C23—C24 | 152.7 (3) |
C4—C5—C9—C8 | −167.51 (17) | O4—C14—N1—C13 | −176.16 (18) |
C25—C8—C9—C10 | 74.10 (19) | N2—C14—N1—C13 | 3.9 (3) |
C7—C8—C9—C10 | −169.13 (15) | O4—C14—N1—C16 | 3.1 (3) |
C12—C8—C9—C10 | −48.2 (2) | N2—C14—N1—C16 | −176.82 (17) |
C25—C8—C9—C5 | −159.52 (15) | O3—C13—N1—C14 | 174.31 (18) |
C7—C8—C9—C5 | −42.75 (19) | C10—C13—N1—C14 | −6.6 (3) |
C12—C8—C9—C5 | 78.14 (18) | O3—C13—N1—C16 | −4.9 (3) |
C5—C9—C10—C11 | −103.3 (2) | C10—C13—N1—C16 | 174.15 (17) |
C8—C9—C10—C11 | 20.3 (2) | O2—C11—N2—C14 | −179.32 (15) |
C5—C9—C10—C13 | 82.0 (2) | C10—C11—N2—C14 | 0.0 (3) |
C8—C9—C10—C13 | −154.41 (16) | O2—C11—N2—C15 | 2.9 (2) |
C13—C10—C11—O2 | 176.38 (16) | C10—C11—N2—C15 | −177.83 (18) |
C9—C10—C11—O2 | 1.6 (3) | O4—C14—N2—C11 | 179.73 (17) |
C13—C10—C11—N2 | −2.8 (3) | N1—C14—N2—C11 | −0.4 (3) |
C9—C10—C11—N2 | −177.56 (16) | O4—C14—N2—C15 | −2.4 (3) |
C25—C8—C12—O2 | −63.45 (19) | N1—C14—N2—C15 | 177.48 (16) |
C7—C8—C12—O2 | 177.89 (14) | C1—C6—O1—C7 | −162.40 (19) |
C9—C8—C12—O2 | 58.46 (19) | C5—C6—O1—C7 | 18.9 (3) |
C25—C8—C12—C17 | 58.0 (2) | C8—C7—O1—C6 | −51.8 (2) |
C7—C8—C12—C17 | −60.7 (2) | C10—C11—O2—C12 | 7.7 (3) |
C9—C8—C12—C17 | 179.90 (15) | N2—C11—O2—C12 | −173.07 (14) |
C11—C10—C13—O3 | −175.21 (18) | C17—C12—O2—C11 | −164.19 (15) |
C9—C10—C13—O3 | −0.4 (3) | C8—C12—O2—C11 | −37.9 (2) |
C11—C10—C13—N1 | 5.8 (3) |
Cg1 and Cg2 are the centroids of rings C14–C19 and C1–C6, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O3 | 0.93 | 2.39 | 3.155 (3) | 139 |
C7—H7B···O4i | 0.97 | 2.52 | 3.423 (3) | 156 |
C15—H15A···O3ii | 0.96 | 2.50 | 3.315 (3) | 143 |
C16—H16C···Cg1iii | 0.96 | 2.93 | 3.739 (2) | 143 |
C24—H24A···Cg2iv | 0.96 | 2.70 | 3.634 (3) | 164 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1/2, y+1/2, −z+1/2; (iii) x−3/2, −y−1/2, z−1/2; (iv) x−1/2, −y−1/2, z−3/2. |
Acknowledgements
The authors thank Dr Babu Varghese, Senior Scientific Officer, SAIF, IIT Madras, Chennai, India, for the data collection.
References
Andrade-Neto, V. F. de, Goulart, M. O. F., da Silva Filho, J. F., da Silva, M. J., Pinto, M. C. F. R., do, C. F. R., Pinto, A. V., Zalis, M. G., Carvalho, L. H. & Krettli, A. U. (2004). Bioorg. Med. Chem. Lett. 14, 1145–1149. Web of Science PubMed Google Scholar
Andrani, L. L. & Lapi, E. (1960). Boll. Chim. Farm. 99, 583–586. PubMed Google Scholar
Bakthadoss, M., Sivakumar, G. & Kannan, D. (2009). Org. Lett. 11, 4466–4469. Web of Science CSD CrossRef PubMed CAS Google Scholar
Bhat, M. A., Siddiqui, N. & Khan, S. A. (2008). Acta. Pol. Pharm. 65, 235–239. Web of Science PubMed CAS Google Scholar
Bianchi, G. & Tava, A. (1987). Agric. Biol. Chem. 51, 2001–2002. CrossRef CAS Google Scholar
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cheng, J.-F., Ishikawa, A., Ono, Y., Arrhenius, T. & Nadzan, A. (2003). Bioorg. Med. Chem. Lett. 13, 3647–3650. Web of Science CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gourdeau, H., Leblond, L., Hamelin, B., Desputeau, C., Dong, K., Kianicka, I., Custeau, D., Boudreau, C., Geerts, L., Cai, S.-X., Drewe, J., Labrecque, D., Kasibhatla, S. & Tseng, B. (2004). Mol. Cancer Ther. 3, 1375–1384. Web of Science PubMed CAS Google Scholar
Groom, C. R. & Allen, F. H. (2014). Angew. Chem. Int. Ed. 53, 662–671. Web of Science CSD CrossRef CAS Google Scholar
Jain, N., Xu, J., Kanojia, R. M., Du, F., Jian-Zhong, G., Pacia, E., Lai, M.-T., Musto, A., Allan, G., Reuman, M., Li, X., Hahn, D. W., Cousineau, M., Peng, S., Ritchie, D., Russell, R., Lundeen, S. & Sui, Z. (2009). J. Med. Chem. 52, 7544–7569. Web of Science CrossRef PubMed CAS Google Scholar
Kanchanadevi, J., Anbalagan, G., Sivakumar, G., Bakthadoss, M. & Manivannan, V. (2011). Acta Cryst. E67, o1990. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kathiravan, S. & Raghunathan, R. (2010). Synlett, 13, 1927–1930. Google Scholar
Khairy, A. M., Mohsen, M. A., Yahia, A. M., Basyouni, W. M. & Samir, Y. A. (2009). WJC, 4, 161–170. Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Mladenović, M., Mihailović, M., Bogojević, D., Matić, S., Nićiforović, N., Mihailović, V., Vuković, N., Sukdolak, S. & Solujić, S. (2011). Int. J. Mol. Sci. 12(5), 2822–2841. Google Scholar
Mohr, S. J., Chirigos, M. A., Fuhrman, F. S. & Pryor, J. W. (1975). Cancer Res. 35, 3750–3754. PubMed CAS Web of Science Google Scholar
Moon, D.-O., Choi, Y. H., Kim, N.-D., Park, Y.-M. & Kim, G.-Y. (2007). Int. Immunopharmacol. 7, 506–514. Web of Science CrossRef PubMed CAS Google Scholar
Ponnusamy, R., Sabari, V., Sivakumar, G., Bakthadoss, M. & Aravindhan, S. (2013). Acta Cryst. E69, o267–o268. CSD CrossRef CAS IUCr Journals Google Scholar
Sangani, C. B., Shah, N. M., Patel, M. P. & Patel, R. G. (2012). J. Serb. Chem. Soc. 77, 1165–1174. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Smith, P. W., Sollis, S. L., Howes, P. D., Cherry, P. C., Starkey, I. D., Cobley, K. N., Weston, H., Scicinski, J., Merritt, A., Whittington, A., Wyatt, P., Taylor, N., Green, D., Bethell, R., Madar, S., Fenton, R. J., Morley, P. J., Pateman, T. & Beresford, A. (1998). J. Med. Chem. 41, 787–797. Web of Science CrossRef CAS PubMed Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Swaminathan, K., Sethusankar, K., Sivakumar, G. & Bakthadoss, M. (2011). Acta Cryst. E67, o2673. Web of Science CSD CrossRef IUCr Journals Google Scholar
Thareja, S., Verma, A., Kalra, A., Gosain, S., Rewatkar, P. V. & Kokil, G. R. (2010). Acta. Pol. Pharm. 67, 423–427. Web of Science CAS PubMed Google Scholar
Tripathi, R. P., Tripathi, R., Bhaduri, A. P., Singh, S. N., Chatterjee, R. K. & Murthy, P. K. (2000). Acta Trop. 76, 101–106. Web of Science CrossRef PubMed CAS Google Scholar
Zhang, Y. L., Chen, B. Z., Zheng, K. Q., Xu, M. L., Lei, X. H. & Yaoxue, X. B. (1982). Chem. Abstr. 96, 135383e. Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.