

Crystal structure of 2-(11-oxo-10H,11H-indeno[1,2-b]chromen-10-yl)-2,3-dihydro-1H-indene-1,3-dione

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015007495/is5397sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2056989015007495/is5397Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015007495/is5397Isup3.cml |
CCDC reference: 1059989
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.035
- wR factor = 0.090
- Data-to-parameter ratio = 13.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 2 Report
Alert level G PLAT793_ALERT_4_G The Model has Chirality at C1 (Centro SPGR) S Verify PLAT793_ALERT_4_G The Model has Chirality at C17 (Centro SPGR) R Verify PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 4 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 3 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
In 30 ml of ethanol, a mixture of 1 mmol (122 mg) of salicylaldehyde and 2 mmol (292 mg) of 1H-indene-1,3(2H)-dione has been refluxed in the presence of a guanidine derivative as a lewise base catalyst. The reaction was monitored by TLC till completion after 5 h. On cooling, the solid product was collected by filteration, dried under vacuum and recrystallized from dimethylformamide (DMF). Single crystals suitable for X-ray diffraction were obtained by further crystallization from DMF. M.p. 513 K.
H-atoms were placed in calculated positions (C—H = 0.95–1.00 Å) and included as riding contributions with isotropic displacement parameters 1.2 times those of the attached carbon atoms.
The synthesis of chromenes scaffolds has attracted considerable attention from organic and medicinal chemists for many years as larg number of natural products contain this heterocyclic nucleus (RamaGanesh et al., 2010). They are widely used as additives in food, perfumes, cosmetics, pharmaceuticals (O'Kenedy & Thornes, 1997), optical brighteners, dispersed fluorescent and laser dyes (Zabradnik, 1992). Fused chromene ring systems have platelet anti-aggregating, local anesthetic (Bargagna et al., 1992) and also exhibit antidepressant effects (Ermili et al., 1979). In this view and following to our study in synthesis of bio-active hetero-cyclic molecules, we report in this study the synthesis and crystal structure of the title compound.
In the title molecule (Fig. 1), there is a slight fold in the larger fused ring moiety along the C1···O1 line with a dihedral angle between the mean planes of C2–C10 and C11–C16 rings being 9.62 (5)°. The dihedral angle between the mean planes of C1–C16/O1 and C17–C25 ring systems is 63.50 (2)°. The molecules associate along the 21 axes via a weak C12—H12···O4i [symmetry code: (i) 1-x, -1/2+y, 1/2-z] hydrogen bond to form a helical chain (Table 1 and Fig. 2). In addition, there is a π–π stacking interaction between the five-membered C2–C4/C9/C10 ring and its centrosymmetrically related counterpart with a centroid-centroid distance of 3.666 (1) Å, an interplanar distance of 3.575 (1) Å and a centroid offset of 0.812 (1) Å.
For synthesis and biological properties of chromene scaffolds, see: RamaGanesh et al. (2010); O'Kenedy & Thornes (1997); Zabradnik (1992). For the bioactivity of fused chromenes, see: Bargagna et al. (1992); Ermili et al. (1979).
Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).
C25H14O4 | F(000) = 784 |
Mr = 378.36 | Dx = 1.418 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 8.7409 (2) Å | Cell parameters from 9790 reflections |
b = 14.4740 (3) Å | θ = 3.1–72.3° |
c = 14.2774 (3) Å | µ = 0.78 mm−1 |
β = 101.141 (1)° | T = 150 K |
V = 1772.28 (7) Å3 | Block, orange |
Z = 4 | 0.23 × 0.22 × 0.11 mm |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 3495 independent reflections |
Radiation source: INCOATEC IµS micro–focus source | 3189 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.030 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 72.4°, θmin = 4.4° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | k = −17→17 |
Tmin = 0.86, Tmax = 0.92 | l = −17→17 |
28946 measured reflections |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.090 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0457P)2 + 0.5107P] where P = (Fo2 + 2Fc2)/3 |
3495 reflections | (Δ/σ)max < 0.001 |
262 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C25H14O4 | V = 1772.28 (7) Å3 |
Mr = 378.36 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 8.7409 (2) Å | µ = 0.78 mm−1 |
b = 14.4740 (3) Å | T = 150 K |
c = 14.2774 (3) Å | 0.23 × 0.22 × 0.11 mm |
β = 101.141 (1)° |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 3495 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | 3189 reflections with I > 2σ(I) |
Tmin = 0.86, Tmax = 0.92 | Rint = 0.030 |
28946 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.090 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.19 e Å−3 |
3495 reflections | Δρmin = −0.21 e Å−3 |
262 parameters |
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. H-atoms were placed in calculated positions (C—H = 0.95 - 1.00 Å) and included as riding contributions with isotropic displacement parameters 1.2 times those of the attached carbon atoms. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.47506 (10) | 0.32965 (6) | 0.40020 (6) | 0.0302 (2) | |
O2 | 0.16356 (11) | 0.59782 (6) | 0.38392 (6) | 0.0352 (2) | |
O3 | 0.08695 (12) | 0.33852 (7) | 0.24206 (6) | 0.0440 (3) | |
O4 | 0.27958 (11) | 0.57260 (6) | 0.06450 (6) | 0.0343 (2) | |
C1 | 0.35974 (13) | 0.48118 (7) | 0.26329 (8) | 0.0240 (2) | |
H1 | 0.4079 | 0.5433 | 0.2586 | 0.029* | |
C2 | 0.33109 (13) | 0.47028 (8) | 0.36229 (8) | 0.0243 (2) | |
C3 | 0.23649 (13) | 0.52859 (8) | 0.41347 (8) | 0.0263 (2) | |
C4 | 0.24407 (13) | 0.48383 (8) | 0.50974 (8) | 0.0266 (2) | |
C5 | 0.17816 (15) | 0.50868 (9) | 0.58577 (9) | 0.0320 (3) | |
H5 | 0.1152 | 0.5624 | 0.5835 | 0.038* | |
C6 | 0.20691 (15) | 0.45208 (10) | 0.66709 (9) | 0.0354 (3) | |
H6 | 0.1624 | 0.4677 | 0.7207 | 0.043* | |
C7 | 0.29864 (15) | 0.37426 (9) | 0.67053 (8) | 0.0352 (3) | |
H7 | 0.3168 | 0.3373 | 0.7266 | 0.042* | |
C8 | 0.36576 (14) | 0.34857 (9) | 0.59259 (8) | 0.0314 (3) | |
H8 | 0.4289 | 0.2949 | 0.5947 | 0.038* | |
C9 | 0.33631 (13) | 0.40432 (8) | 0.51294 (8) | 0.0260 (2) | |
C10 | 0.38543 (13) | 0.39924 (8) | 0.42012 (8) | 0.0248 (2) | |
C11 | 0.52713 (13) | 0.33794 (8) | 0.31358 (8) | 0.0262 (2) | |
C12 | 0.63660 (14) | 0.27212 (8) | 0.30077 (9) | 0.0314 (3) | |
H12 | 0.6658 | 0.2247 | 0.3468 | 0.038* | |
C13 | 0.70268 (14) | 0.27624 (9) | 0.22043 (9) | 0.0337 (3) | |
H13 | 0.7782 | 0.2317 | 0.2110 | 0.040* | |
C14 | 0.65849 (14) | 0.34552 (9) | 0.15348 (9) | 0.0330 (3) | |
H14 | 0.7039 | 0.3487 | 0.0983 | 0.040* | |
C15 | 0.54789 (14) | 0.41008 (8) | 0.16735 (8) | 0.0291 (3) | |
H15 | 0.5188 | 0.4572 | 0.1210 | 0.035* | |
C16 | 0.47777 (13) | 0.40800 (8) | 0.24747 (8) | 0.0248 (2) | |
C17 | 0.20346 (13) | 0.47769 (8) | 0.18908 (8) | 0.0255 (2) | |
H17 | 0.1298 | 0.5231 | 0.2091 | 0.031* | |
C18 | 0.12395 (13) | 0.38332 (8) | 0.17816 (8) | 0.0280 (3) | |
C19 | 0.10045 (12) | 0.35606 (8) | 0.07625 (8) | 0.0253 (2) | |
C20 | 0.03310 (14) | 0.27627 (8) | 0.03180 (9) | 0.0307 (3) | |
H20 | −0.0095 | 0.2302 | 0.0666 | 0.037* | |
C21 | 0.03053 (14) | 0.26658 (8) | −0.06495 (9) | 0.0332 (3) | |
H21 | −0.0141 | 0.2126 | −0.0969 | 0.040* | |
C22 | 0.09206 (15) | 0.33439 (9) | −0.11675 (9) | 0.0334 (3) | |
H22 | 0.0893 | 0.3255 | −0.1830 | 0.040* | |
C23 | 0.15714 (14) | 0.41447 (8) | −0.07265 (8) | 0.0303 (3) | |
H23 | 0.1982 | 0.4610 | −0.1077 | 0.036* | |
C24 | 0.16014 (13) | 0.42425 (7) | 0.02446 (8) | 0.0251 (2) | |
C25 | 0.22245 (13) | 0.50203 (8) | 0.08798 (8) | 0.0258 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0330 (4) | 0.0288 (4) | 0.0296 (4) | 0.0069 (3) | 0.0081 (3) | 0.0060 (3) |
O2 | 0.0399 (5) | 0.0292 (4) | 0.0385 (5) | 0.0078 (4) | 0.0125 (4) | 0.0058 (4) |
O3 | 0.0468 (6) | 0.0541 (6) | 0.0294 (5) | −0.0207 (5) | 0.0036 (4) | 0.0110 (4) |
O4 | 0.0468 (5) | 0.0261 (4) | 0.0291 (4) | −0.0079 (4) | 0.0049 (4) | 0.0039 (3) |
C1 | 0.0249 (5) | 0.0234 (5) | 0.0231 (5) | −0.0017 (4) | 0.0033 (4) | 0.0008 (4) |
C2 | 0.0236 (5) | 0.0248 (5) | 0.0234 (5) | −0.0020 (4) | 0.0015 (4) | −0.0006 (4) |
C3 | 0.0254 (5) | 0.0256 (5) | 0.0272 (6) | −0.0028 (4) | 0.0037 (4) | −0.0008 (4) |
C4 | 0.0256 (5) | 0.0280 (6) | 0.0249 (5) | −0.0048 (4) | 0.0014 (4) | −0.0016 (4) |
C5 | 0.0331 (6) | 0.0334 (6) | 0.0296 (6) | −0.0035 (5) | 0.0060 (5) | −0.0047 (5) |
C6 | 0.0355 (7) | 0.0474 (7) | 0.0237 (6) | −0.0090 (6) | 0.0065 (5) | −0.0042 (5) |
C7 | 0.0346 (6) | 0.0458 (7) | 0.0234 (6) | −0.0079 (6) | 0.0010 (5) | 0.0059 (5) |
C8 | 0.0286 (6) | 0.0358 (6) | 0.0274 (6) | −0.0023 (5) | −0.0004 (5) | 0.0047 (5) |
C9 | 0.0233 (5) | 0.0290 (6) | 0.0241 (5) | −0.0045 (4) | 0.0004 (4) | −0.0006 (4) |
C10 | 0.0221 (5) | 0.0255 (5) | 0.0255 (5) | −0.0016 (4) | 0.0011 (4) | −0.0009 (4) |
C11 | 0.0250 (5) | 0.0270 (6) | 0.0263 (6) | −0.0018 (4) | 0.0039 (4) | −0.0002 (4) |
C12 | 0.0291 (6) | 0.0273 (6) | 0.0366 (6) | 0.0019 (5) | 0.0028 (5) | 0.0004 (5) |
C13 | 0.0276 (6) | 0.0328 (6) | 0.0408 (7) | 0.0030 (5) | 0.0067 (5) | −0.0064 (5) |
C14 | 0.0285 (6) | 0.0383 (7) | 0.0332 (6) | −0.0027 (5) | 0.0088 (5) | −0.0041 (5) |
C15 | 0.0267 (6) | 0.0317 (6) | 0.0286 (6) | −0.0027 (5) | 0.0043 (5) | 0.0009 (5) |
C16 | 0.0217 (5) | 0.0247 (5) | 0.0271 (5) | −0.0033 (4) | 0.0022 (4) | −0.0014 (4) |
C17 | 0.0263 (6) | 0.0264 (5) | 0.0233 (5) | 0.0017 (4) | 0.0032 (4) | 0.0032 (4) |
C18 | 0.0223 (5) | 0.0336 (6) | 0.0269 (6) | −0.0018 (5) | 0.0014 (4) | 0.0070 (5) |
C19 | 0.0214 (5) | 0.0257 (5) | 0.0277 (6) | 0.0019 (4) | 0.0021 (4) | 0.0045 (4) |
C20 | 0.0268 (6) | 0.0264 (6) | 0.0367 (6) | −0.0022 (5) | 0.0010 (5) | 0.0059 (5) |
C21 | 0.0324 (6) | 0.0259 (6) | 0.0387 (7) | −0.0007 (5) | 0.0006 (5) | −0.0046 (5) |
C22 | 0.0370 (7) | 0.0345 (6) | 0.0287 (6) | −0.0001 (5) | 0.0063 (5) | −0.0046 (5) |
C23 | 0.0337 (6) | 0.0304 (6) | 0.0272 (6) | −0.0027 (5) | 0.0069 (5) | 0.0014 (5) |
C24 | 0.0243 (5) | 0.0237 (5) | 0.0265 (6) | 0.0012 (4) | 0.0031 (4) | 0.0025 (4) |
C25 | 0.0272 (5) | 0.0242 (5) | 0.0251 (5) | 0.0012 (4) | 0.0025 (4) | 0.0037 (4) |
O1—C10 | 1.3400 (14) | C11—C16 | 1.3956 (16) |
O1—C11 | 1.4030 (13) | C12—C13 | 1.3817 (18) |
O2—C3 | 1.2185 (14) | C12—H12 | 0.9500 |
O3—C18 | 1.2131 (14) | C13—C14 | 1.3877 (18) |
O4—C25 | 1.2123 (14) | C13—H13 | 0.9500 |
C1—C2 | 1.4906 (15) | C14—C15 | 1.3861 (17) |
C1—C16 | 1.5256 (15) | C14—H14 | 0.9500 |
C1—C17 | 1.5595 (15) | C15—C16 | 1.3986 (16) |
C1—H1 | 1.0000 | C15—H15 | 0.9500 |
C2—C10 | 1.3464 (16) | C17—C25 | 1.5256 (15) |
C2—C3 | 1.4709 (16) | C17—C18 | 1.5268 (16) |
C3—C4 | 1.5093 (16) | C17—H17 | 1.0000 |
C4—C5 | 1.3715 (17) | C18—C19 | 1.4829 (16) |
C4—C9 | 1.4008 (16) | C19—C20 | 1.3924 (16) |
C5—C6 | 1.4034 (18) | C19—C24 | 1.3937 (15) |
C5—H5 | 0.9500 | C20—C21 | 1.3843 (18) |
C6—C7 | 1.378 (2) | C20—H20 | 0.9500 |
C6—H6 | 0.9500 | C21—C22 | 1.3977 (18) |
C7—C8 | 1.4047 (18) | C21—H21 | 0.9500 |
C7—H7 | 0.9500 | C22—C23 | 1.3874 (17) |
C8—C9 | 1.3775 (16) | C22—H22 | 0.9500 |
C8—H8 | 0.9500 | C23—C24 | 1.3888 (16) |
C9—C10 | 1.4717 (15) | C23—H23 | 0.9500 |
C11—C12 | 1.3873 (16) | C24—C25 | 1.4818 (16) |
C10—O1—C11 | 115.17 (9) | C12—C13—H13 | 120.1 |
C2—C1—C16 | 108.01 (9) | C14—C13—H13 | 120.1 |
C2—C1—C17 | 110.81 (9) | C15—C14—C13 | 119.85 (11) |
C16—C1—C17 | 113.92 (9) | C15—C14—H14 | 120.1 |
C2—C1—H1 | 108.0 | C13—C14—H14 | 120.1 |
C16—C1—H1 | 108.0 | C14—C15—C16 | 122.03 (11) |
C17—C1—H1 | 108.0 | C14—C15—H15 | 119.0 |
C10—C2—C3 | 107.40 (10) | C16—C15—H15 | 119.0 |
C10—C2—C1 | 123.94 (10) | C11—C16—C15 | 116.22 (10) |
C3—C2—C1 | 128.60 (10) | C11—C16—C1 | 122.27 (10) |
O2—C3—C2 | 127.35 (11) | C15—C16—C1 | 121.46 (10) |
O2—C3—C4 | 126.60 (11) | C25—C17—C18 | 103.92 (9) |
C2—C3—C4 | 106.03 (9) | C25—C17—C1 | 113.22 (9) |
C5—C4—C9 | 121.12 (11) | C18—C17—C1 | 114.84 (9) |
C5—C4—C3 | 131.06 (11) | C25—C17—H17 | 108.2 |
C9—C4—C3 | 107.82 (10) | C18—C17—H17 | 108.2 |
C4—C5—C6 | 117.79 (12) | C1—C17—H17 | 108.2 |
C4—C5—H5 | 121.1 | O3—C18—C19 | 126.10 (11) |
C6—C5—H5 | 121.1 | O3—C18—C17 | 125.71 (11) |
C7—C6—C5 | 121.10 (11) | C19—C18—C17 | 108.20 (9) |
C7—C6—H6 | 119.4 | C20—C19—C24 | 120.94 (11) |
C5—C6—H6 | 119.4 | C20—C19—C18 | 129.36 (10) |
C6—C7—C8 | 121.16 (11) | C24—C19—C18 | 109.70 (10) |
C6—C7—H7 | 119.4 | C21—C20—C19 | 117.57 (11) |
C8—C7—H7 | 119.4 | C21—C20—H20 | 121.2 |
C9—C8—C7 | 117.31 (12) | C19—C20—H20 | 121.2 |
C9—C8—H8 | 121.3 | C20—C21—C22 | 121.54 (11) |
C7—C8—H8 | 121.3 | C20—C21—H21 | 119.2 |
C8—C9—C4 | 121.52 (11) | C22—C21—H21 | 119.2 |
C8—C9—C10 | 132.35 (11) | C23—C22—C21 | 120.82 (11) |
C4—C9—C10 | 106.13 (10) | C23—C22—H22 | 119.6 |
O1—C10—C2 | 126.54 (10) | C21—C22—H22 | 119.6 |
O1—C10—C9 | 120.86 (10) | C22—C23—C24 | 117.73 (11) |
C2—C10—C9 | 112.60 (10) | C22—C23—H23 | 121.1 |
C12—C11—C16 | 122.74 (11) | C24—C23—H23 | 121.1 |
C12—C11—O1 | 114.01 (10) | C23—C24—C19 | 121.38 (11) |
C16—C11—O1 | 123.21 (10) | C23—C24—C25 | 128.48 (10) |
C13—C12—C11 | 119.30 (11) | C19—C24—C25 | 110.14 (10) |
C13—C12—H12 | 120.3 | O4—C25—C24 | 126.38 (10) |
C11—C12—H12 | 120.3 | O4—C25—C17 | 125.60 (10) |
C12—C13—C14 | 119.85 (11) | C24—C25—C17 | 108.02 (9) |
C16—C1—C2—C10 | −8.40 (14) | O1—C11—C16—C15 | 176.14 (10) |
C17—C1—C2—C10 | 117.03 (12) | C12—C11—C16—C1 | −178.73 (10) |
C16—C1—C2—C3 | 174.83 (10) | O1—C11—C16—C1 | −1.09 (17) |
C17—C1—C2—C3 | −59.74 (14) | C14—C15—C16—C11 | 0.92 (17) |
C10—C2—C3—O2 | −177.52 (11) | C14—C15—C16—C1 | 178.17 (10) |
C1—C2—C3—O2 | −0.33 (19) | C2—C1—C16—C11 | 7.86 (14) |
C10—C2—C3—C4 | 0.95 (12) | C17—C1—C16—C11 | −115.70 (11) |
C1—C2—C3—C4 | 178.15 (10) | C2—C1—C16—C15 | −169.22 (10) |
O2—C3—C4—C5 | −1.7 (2) | C17—C1—C16—C15 | 67.21 (13) |
C2—C3—C4—C5 | 179.85 (12) | C2—C1—C17—C25 | 171.83 (9) |
O2—C3—C4—C9 | 178.00 (11) | C16—C1—C17—C25 | −66.13 (12) |
C2—C3—C4—C9 | −0.49 (12) | C2—C1—C17—C18 | −69.02 (12) |
C9—C4—C5—C6 | 0.34 (17) | C16—C1—C17—C18 | 53.01 (13) |
C3—C4—C5—C6 | 179.97 (11) | C25—C17—C18—O3 | −179.89 (12) |
C4—C5—C6—C7 | 0.17 (18) | C1—C17—C18—O3 | 55.90 (16) |
C5—C6—C7—C8 | −0.39 (19) | C25—C17—C18—C19 | 0.28 (11) |
C6—C7—C8—C9 | 0.09 (18) | C1—C17—C18—C19 | −123.93 (10) |
C7—C8—C9—C4 | 0.42 (17) | O3—C18—C19—C20 | 0.1 (2) |
C7—C8—C9—C10 | −179.89 (11) | C17—C18—C19—C20 | 179.97 (11) |
C5—C4—C9—C8 | −0.65 (17) | O3—C18—C19—C24 | −178.97 (12) |
C3—C4—C9—C8 | 179.64 (10) | C17—C18—C19—C24 | 0.86 (12) |
C5—C4—C9—C10 | 179.59 (10) | C24—C19—C20—C21 | 1.22 (17) |
C3—C4—C9—C10 | −0.12 (12) | C18—C19—C20—C21 | −177.80 (11) |
C11—O1—C10—C2 | 6.15 (16) | C19—C20—C21—C22 | −0.44 (18) |
C11—O1—C10—C9 | −173.60 (9) | C20—C21—C22—C23 | −0.48 (19) |
C3—C2—C10—O1 | 179.16 (10) | C21—C22—C23—C24 | 0.59 (18) |
C1—C2—C10—O1 | 1.80 (18) | C22—C23—C24—C19 | 0.20 (17) |
C3—C2—C10—C9 | −1.08 (13) | C22—C23—C24—C25 | 179.92 (11) |
C1—C2—C10—C9 | −178.44 (10) | C20—C19—C24—C23 | −1.13 (17) |
C8—C9—C10—O1 | 0.82 (19) | C18—C19—C24—C23 | 178.07 (10) |
C4—C9—C10—O1 | −179.45 (10) | C20—C19—C24—C25 | 179.10 (10) |
C8—C9—C10—C2 | −178.95 (12) | C18—C19—C24—C25 | −1.70 (13) |
C4—C9—C10—C2 | 0.77 (13) | C23—C24—C25—O4 | 1.7 (2) |
C10—O1—C11—C12 | 171.53 (10) | C19—C24—C25—O4 | −178.55 (11) |
C10—O1—C11—C16 | −6.30 (15) | C23—C24—C25—C17 | −177.87 (11) |
C16—C11—C12—C13 | 1.24 (18) | C19—C24—C25—C17 | 1.87 (12) |
O1—C11—C12—C13 | −176.60 (10) | C18—C17—C25—O4 | 179.17 (11) |
C11—C12—C13—C14 | −0.34 (18) | C1—C17—C25—O4 | −55.58 (15) |
C12—C13—C14—C15 | −0.22 (18) | C18—C17—C25—C24 | −1.26 (11) |
C13—C14—C15—C16 | −0.09 (18) | C1—C17—C25—C24 | 124.00 (10) |
C12—C11—C16—C15 | −1.50 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···O4i | 0.95 | 2.54 | 3.4687 (15) | 166 |
Symmetry code: (i) −x+1, y−1/2, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···O4i | 0.95 | 2.54 | 3.4687 (15) | 166 |
Symmetry code: (i) −x+1, y−1/2, −z+1/2. |
The synthesis of chromenes scaffolds has attracted considerable attention from organic and medicinal chemists for many years as larg number of natural products contain this heterocyclic nucleus (RamaGanesh et al., 2010). They are widely used as additives in food, perfumes, cosmetics, pharmaceuticals (O'Kenedy & Thornes, 1997), optical brighteners, dispersed fluorescent and laser dyes (Zabradnik, 1992). Fused chromene ring systems have platelet anti-aggregating, local anesthetic (Bargagna et al., 1992) and also exhibit antidepressant effects (Ermili et al., 1979). In this view and following to our study in synthesis of bio-active hetero-cyclic molecules, we report in this study the synthesis and crystal structure of the title compound.
In the title molecule (Fig. 1), there is a slight fold in the larger fused ring moiety along the C1···O1 line with a dihedral angle between the mean planes of C2–C10 and C11–C16 rings being 9.62 (5)°. The dihedral angle between the mean planes of C1–C16/O1 and C17–C25 ring systems is 63.50 (2)°. The molecules associate along the 21 axes via a weak C12—H12···O4i [symmetry code: (i) 1-x, -1/2+y, 1/2-z] hydrogen bond to form a helical chain (Table 1 and Fig. 2). In addition, there is a π–π stacking interaction between the five-membered C2–C4/C9/C10 ring and its centrosymmetrically related counterpart with a centroid-centroid distance of 3.666 (1) Å, an interplanar distance of 3.575 (1) Å and a centroid offset of 0.812 (1) Å.