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organic compounds
12-(2-Hydroxy-6-oxocyclohex-1-enyl)-9,10-dihydro-8H-benzo[a]xanthen-11(12H)-one
aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, bChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England, Chemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, cDepartment of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland, dChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, UK, eAnalytical Sciences, Manchester Metropolitan University, Manchester, M1 5GD, England, and fDepartment of Chemistry, College of Science, Kirkuk University, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com
In the xanthenone system of the title compound, C23H20O4, the pyran ring has a maximum deviation of 0.111 (1) Å from planarity and the outer cyclohexene ring exhibits a puckered conformation. The three methylene C atoms of the cyclohexene ring bonded to the pyran unit are disordered over two sets of sites [occupancies = 0.570 (3) and 0.430 (3)]. In the crystal, molecules are linked by C—H⋯O and O—H⋯O hydrogen bonds, forming a two-dimensional network parallel to (110). A C—H⋯π interaction occurs between these networks.
CCDC reference: 960705
Related literature
For related xanthenone structures, see: Li et al. (2004); Abdelhamid et al. (2011
); Mohamed et al. (2011
, 2012
). Reddy et al. (2009
); Çelik et al. (2009
). For the industrial and pharmaceutical significance of xanthenes, see: Zare et al. (2012
); Menchen et al. (2003a
,b
); Sarma & Baruah, (2005
). For ring conformations, see: Cremer & Pople (1975
) and for standard bond lengths, see: Allen et al. (1987
).
Experimental
Crystal data
|
|
Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell CrysAlis PRO; data reduction: CrysAlis PRO; 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
); software used to prepare material for publication: WinGX (Farrugia, 2012
) and PLATON (Spek, 2009
).
Supporting information
CCDC reference: 960705
10.1107/S1600536813025324/sj5351sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536813025324/sj5351Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536813025324/sj5351Isup3.cml
The title compound was obtained as the main product during a three component reaction of 1 mmol (206 mg) 4-nitro-2-(trifluoromethyl)aniline, 1 mmol (172 mg) 2-hydroxy-1-naphthaldehyde and 1 mmol (112 mg) 1,3-cyclohexandione in 50 ml ethanol. The reaction mixture was refluxed for 7 h at 351 K. On cooling, the resulting solid was collected, washed with cold ethanol and dried by filtration. The crude product was crystallized by the slow evaporation method over 24 h using ethanol as a solvent. M.p. = 517 K, yield = 95%.
The hydroxyl H atoms were found from a difference Fourier map and refined freely. The C-bound H-atoms were refined using a riding model with C—H = 0.95 - 1.00 Å and Uĩso(H) = 1.2Ueq(C). The three methylene C atoms (C20/C21/C22) of the other cyclohexene ring bonded to the pyran moiety are disordered over two sets of sites with a ratio of refined occupancies of 0.570 (3): 0.430 (3) [in the
DFIX and EADP instructions were used for the disordered atoms].Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell
CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); 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); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).C23H20O4 | F(000) = 1520 |
Mr = 360.41 | Dx = 1.325 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 3838 reflections |
a = 14.2855 (15) Å | θ = 3.0–29.5° |
b = 13.7461 (12) Å | µ = 0.09 mm−1 |
c = 18.400 (2) Å | T = 123 K |
V = 3613.2 (6) Å3 | Block, colourless |
Z = 8 | 0.20 × 0.18 × 0.16 mm |
Oxford Diffraction Xcalibur, Eos diffractometer | 4541 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3366 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
Detector resolution: 16.0727 pixels mm-1 | θmax = 29.5°, θmin = 3.0° |
ω scans | h = −18→18 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | k = −17→17 |
Tmin = 0.994, Tmax = 1.000 | l = −16→25 |
17944 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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.037P)2 + 1.8151P] where P = (Fo2 + 2Fc2)/3 |
4541 reflections | (Δ/σ)max = 0.001 |
258 parameters | Δρmax = 0.40 e Å−3 |
8 restraints | Δρmin = −0.25 e Å−3 |
C23H20O4 | V = 3613.2 (6) Å3 |
Mr = 360.41 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 14.2855 (15) Å | µ = 0.09 mm−1 |
b = 13.7461 (12) Å | T = 123 K |
c = 18.400 (2) Å | 0.20 × 0.18 × 0.16 mm |
Oxford Diffraction Xcalibur, Eos diffractometer | 4541 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | 3366 reflections with I > 2σ(I) |
Tmin = 0.994, Tmax = 1.000 | Rint = 0.042 |
17944 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 8 restraints |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.40 e Å−3 |
4541 reflections | Δρmin = −0.25 e Å−3 |
258 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.03562 (8) | 0.89828 (7) | 0.24583 (6) | 0.0232 (3) | |
O2 | 0.02801 (9) | 0.61517 (8) | 0.38998 (6) | 0.0269 (4) | |
O3 | 0.18481 (8) | 0.51704 (7) | 0.29379 (7) | 0.0245 (3) | |
O4 | 0.22989 (8) | 0.85224 (7) | 0.30414 (6) | 0.0206 (3) | |
C1 | 0.11053 (11) | 0.75665 (10) | 0.19287 (8) | 0.0170 (4) | |
C2 | 0.14830 (11) | 0.71387 (10) | 0.12835 (8) | 0.0190 (4) | |
C3 | 0.18506 (11) | 0.61770 (11) | 0.12698 (9) | 0.0208 (4) | |
C4 | 0.21973 (12) | 0.57841 (12) | 0.06413 (9) | 0.0259 (5) | |
C5 | 0.21989 (12) | 0.63171 (13) | −0.00100 (9) | 0.0289 (5) | |
C6 | 0.18492 (12) | 0.72413 (12) | −0.00158 (9) | 0.0279 (5) | |
C7 | 0.14894 (12) | 0.76802 (11) | 0.06208 (9) | 0.0233 (5) | |
C8 | 0.11215 (13) | 0.86400 (11) | 0.06150 (9) | 0.0275 (5) | |
C9 | 0.07720 (12) | 0.90419 (11) | 0.12294 (9) | 0.0264 (5) | |
C10 | 0.07683 (11) | 0.84974 (11) | 0.18784 (9) | 0.0206 (4) | |
C11 | 0.10633 (10) | 0.70142 (9) | 0.26465 (8) | 0.0150 (4) | |
C12 | 0.04078 (10) | 0.75335 (10) | 0.31646 (8) | 0.0173 (4) | |
C13 | 0.00454 (11) | 0.69966 (11) | 0.37919 (9) | 0.0212 (5) | |
C14 | −0.06429 (13) | 0.75053 (13) | 0.42855 (10) | 0.0330 (6) | |
C15 | −0.04989 (15) | 0.86009 (13) | 0.43098 (11) | 0.0370 (6) | |
C16 | −0.05019 (13) | 0.90186 (12) | 0.35487 (10) | 0.0288 (5) | |
C17 | 0.01241 (11) | 0.84547 (11) | 0.30557 (9) | 0.0205 (4) | |
C18 | 0.20297 (10) | 0.68519 (10) | 0.29769 (8) | 0.0145 (4) | |
C19 | 0.23694 (11) | 0.59364 (10) | 0.31102 (8) | 0.0180 (4) | |
C20B | 0.3353 (4) | 0.5759 (6) | 0.3367 (5) | 0.0207 (11) | 0.570 (3) |
C21B | 0.3740 (2) | 0.66151 (19) | 0.37967 (17) | 0.0236 (7) | 0.570 (3) |
C22B | 0.3603 (5) | 0.7555 (5) | 0.3376 (5) | 0.0214 (11) | 0.570 (3) |
C23 | 0.26030 (11) | 0.76828 (10) | 0.31416 (8) | 0.0160 (4) | |
C22A | 0.3539 (7) | 0.7519 (7) | 0.3496 (7) | 0.0214 (11) | 0.430 (3) |
C20A | 0.3268 (6) | 0.5728 (8) | 0.3504 (7) | 0.0207 (11) | 0.430 (3) |
C21A | 0.3963 (3) | 0.6529 (3) | 0.3323 (2) | 0.0236 (7) | 0.430 (3) |
H3A | 0.18560 | 0.58020 | 0.17030 | 0.0250* | |
H6 | 0.18470 | 0.75980 | −0.04580 | 0.0330* | |
H4 | 0.24410 | 0.51410 | 0.06460 | 0.0310* | |
H5 | 0.24410 | 0.60370 | −0.04430 | 0.0350* | |
H3 | 0.2178 (17) | 0.4587 (17) | 0.3029 (12) | 0.060 (7)* | |
H14A | −0.05800 | 0.72400 | 0.47830 | 0.0400* | |
H14B | −0.12870 | 0.73660 | 0.41160 | 0.0400* | |
H15A | −0.10050 | 0.89050 | 0.45990 | 0.0440* | |
H15B | 0.01050 | 0.87490 | 0.45490 | 0.0440* | |
H16A | −0.11480 | 0.90080 | 0.33540 | 0.0350* | |
H16B | −0.02910 | 0.97040 | 0.35650 | 0.0350* | |
H20C | 0.37600 | 0.56360 | 0.29420 | 0.0250* | 0.570 (3) |
H20D | 0.33630 | 0.51700 | 0.36770 | 0.0250* | 0.570 (3) |
H21C | 0.34160 | 0.66600 | 0.42710 | 0.0280* | 0.570 (3) |
H21D | 0.44160 | 0.65130 | 0.38910 | 0.0280* | 0.570 (3) |
H22C | 0.37900 | 0.81120 | 0.36840 | 0.0260* | 0.570 (3) |
H22D | 0.40120 | 0.75510 | 0.29410 | 0.0260* | 0.570 (3) |
H8 | 0.11210 | 0.90030 | 0.01760 | 0.0330* | |
H9 | 0.05310 | 0.96860 | 0.12230 | 0.0320* | |
H11 | 0.07880 | 0.63600 | 0.25440 | 0.0180* | |
H20A | 0.35200 | 0.50900 | 0.33500 | 0.0250* | 0.430 (3) |
H20B | 0.31560 | 0.57080 | 0.40350 | 0.0250* | 0.430 (3) |
H21A | 0.41270 | 0.64980 | 0.28010 | 0.0280* | 0.430 (3) |
H21B | 0.45420 | 0.64360 | 0.36100 | 0.0280* | 0.430 (3) |
H22A | 0.34670 | 0.75800 | 0.40290 | 0.0260* | 0.430 (3) |
H22B | 0.39770 | 0.80330 | 0.33340 | 0.0260* | 0.430 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0271 (6) | 0.0151 (5) | 0.0274 (6) | 0.0044 (4) | −0.0008 (5) | 0.0007 (4) |
O2 | 0.0325 (7) | 0.0199 (6) | 0.0284 (6) | −0.0053 (5) | 0.0035 (5) | 0.0024 (5) |
O3 | 0.0248 (6) | 0.0096 (5) | 0.0392 (7) | 0.0003 (4) | −0.0094 (5) | −0.0003 (4) |
O4 | 0.0222 (6) | 0.0106 (5) | 0.0290 (6) | −0.0015 (4) | 0.0001 (5) | 0.0000 (4) |
C1 | 0.0156 (7) | 0.0143 (7) | 0.0212 (8) | −0.0028 (6) | −0.0029 (6) | 0.0018 (6) |
C2 | 0.0161 (7) | 0.0197 (7) | 0.0213 (8) | −0.0045 (6) | −0.0029 (6) | 0.0004 (6) |
C3 | 0.0208 (8) | 0.0196 (7) | 0.0220 (8) | −0.0029 (6) | −0.0009 (7) | −0.0006 (6) |
C4 | 0.0242 (9) | 0.0240 (8) | 0.0295 (9) | −0.0024 (7) | 0.0017 (7) | −0.0052 (7) |
C5 | 0.0264 (9) | 0.0385 (10) | 0.0219 (8) | −0.0062 (7) | 0.0028 (7) | −0.0075 (7) |
C6 | 0.0267 (9) | 0.0370 (9) | 0.0201 (8) | −0.0090 (7) | −0.0026 (7) | 0.0037 (7) |
C7 | 0.0213 (8) | 0.0263 (8) | 0.0222 (8) | −0.0070 (6) | −0.0033 (7) | 0.0027 (7) |
C8 | 0.0309 (10) | 0.0265 (8) | 0.0251 (9) | −0.0054 (7) | −0.0053 (8) | 0.0098 (7) |
C9 | 0.0290 (9) | 0.0170 (7) | 0.0333 (10) | −0.0004 (6) | −0.0064 (8) | 0.0069 (7) |
C10 | 0.0197 (8) | 0.0173 (7) | 0.0249 (8) | −0.0014 (6) | −0.0026 (7) | 0.0000 (6) |
C11 | 0.0158 (7) | 0.0105 (6) | 0.0186 (7) | −0.0009 (5) | −0.0010 (6) | −0.0002 (5) |
C12 | 0.0129 (7) | 0.0171 (7) | 0.0220 (8) | −0.0009 (6) | −0.0013 (6) | −0.0028 (6) |
C13 | 0.0168 (8) | 0.0231 (8) | 0.0236 (8) | −0.0040 (6) | −0.0013 (7) | −0.0018 (6) |
C14 | 0.0263 (10) | 0.0400 (10) | 0.0326 (10) | 0.0039 (8) | 0.0110 (8) | 0.0010 (8) |
C15 | 0.0332 (11) | 0.0389 (10) | 0.0390 (11) | 0.0124 (8) | 0.0068 (9) | −0.0085 (8) |
C16 | 0.0237 (9) | 0.0242 (8) | 0.0386 (10) | 0.0067 (7) | 0.0018 (8) | −0.0061 (7) |
C17 | 0.0161 (8) | 0.0192 (7) | 0.0261 (8) | 0.0008 (6) | −0.0027 (7) | −0.0023 (6) |
C18 | 0.0147 (7) | 0.0138 (6) | 0.0150 (7) | 0.0005 (5) | 0.0004 (6) | −0.0003 (5) |
C19 | 0.0189 (8) | 0.0137 (7) | 0.0213 (8) | 0.0003 (6) | −0.0010 (6) | −0.0011 (6) |
C20B | 0.0199 (13) | 0.0172 (8) | 0.025 (3) | 0.0027 (9) | −0.0037 (16) | 0.0015 (15) |
C21B | 0.0171 (12) | 0.0240 (11) | 0.0297 (13) | 0.0017 (9) | −0.0052 (11) | −0.0040 (12) |
C22B | 0.0152 (11) | 0.0190 (9) | 0.030 (3) | −0.0042 (9) | 0.0005 (15) | −0.0012 (14) |
C23 | 0.0166 (7) | 0.0153 (7) | 0.0161 (7) | −0.0005 (5) | 0.0026 (6) | −0.0006 (6) |
C22A | 0.0152 (11) | 0.0190 (9) | 0.030 (3) | −0.0042 (9) | 0.0005 (15) | −0.0012 (14) |
C20A | 0.0199 (13) | 0.0172 (8) | 0.025 (3) | 0.0027 (9) | −0.0037 (16) | 0.0015 (15) |
C21A | 0.0171 (12) | 0.0240 (11) | 0.0297 (13) | 0.0017 (9) | −0.0052 (11) | −0.0040 (12) |
O1—C10 | 1.3894 (19) | C20B—C21B | 1.522 (9) |
O1—C17 | 1.3584 (19) | C21A—C22A | 1.523 (11) |
O2—C13 | 1.2250 (19) | C21B—C22B | 1.519 (8) |
O3—C19 | 1.3281 (18) | C22A—C23 | 1.505 (11) |
O4—C23 | 1.2469 (17) | C22B—C23 | 1.503 (8) |
O3—H3 | 0.95 (2) | C3—H3A | 0.9500 |
C1—C10 | 1.370 (2) | C4—H4 | 0.9500 |
C1—C11 | 1.525 (2) | C5—H5 | 0.9500 |
C1—C2 | 1.431 (2) | C6—H6 | 0.9500 |
C2—C3 | 1.423 (2) | C8—H8 | 0.9500 |
C2—C7 | 1.429 (2) | C9—H9 | 0.9500 |
C3—C4 | 1.369 (2) | C11—H11 | 1.0000 |
C4—C5 | 1.405 (2) | C14—H14A | 0.9900 |
C5—C6 | 1.365 (2) | C14—H14B | 0.9900 |
C6—C7 | 1.414 (2) | C15—H15A | 0.9900 |
C7—C8 | 1.420 (2) | C15—H15B | 0.9900 |
C8—C9 | 1.354 (2) | C16—H16A | 0.9900 |
C9—C10 | 1.409 (2) | C16—H16B | 0.9900 |
C11—C18 | 1.525 (2) | C20A—H20B | 0.9900 |
C11—C12 | 1.515 (2) | C20A—H20A | 0.9900 |
C12—C13 | 1.465 (2) | C20B—H20D | 0.9900 |
C12—C17 | 1.345 (2) | C20B—H20C | 0.9900 |
C13—C14 | 1.510 (2) | C21A—H21B | 0.9900 |
C14—C15 | 1.521 (3) | C21A—H21A | 0.9900 |
C15—C16 | 1.514 (3) | C21B—H21D | 0.9900 |
C16—C17 | 1.491 (2) | C21B—H21C | 0.9900 |
C18—C23 | 1.438 (2) | C22A—H22B | 0.9900 |
C18—C19 | 1.371 (2) | C22A—H22A | 0.9900 |
C19—C20B | 1.502 (6) | C22B—H22D | 0.9900 |
C19—C20A | 1.502 (10) | C22B—H22C | 0.9900 |
C20A—C21A | 1.520 (11) | ||
C10—O1—C17 | 117.92 (11) | C5—C4—H4 | 120.00 |
C19—O3—H3 | 110.5 (14) | C4—C5—H5 | 120.00 |
C2—C1—C11 | 121.94 (12) | C6—C5—H5 | 120.00 |
C10—C1—C11 | 120.64 (13) | C5—C6—H6 | 119.00 |
C2—C1—C10 | 117.41 (13) | C7—C6—H6 | 119.00 |
C1—C2—C7 | 119.77 (13) | C7—C8—H8 | 120.00 |
C3—C2—C7 | 117.82 (14) | C9—C8—H8 | 120.00 |
C1—C2—C3 | 122.41 (13) | C8—C9—H9 | 120.00 |
C2—C3—C4 | 121.00 (15) | C10—C9—H9 | 120.00 |
C3—C4—C5 | 121.03 (15) | C1—C11—H11 | 107.00 |
C4—C5—C6 | 119.44 (15) | C12—C11—H11 | 107.00 |
C5—C6—C7 | 121.57 (15) | C18—C11—H11 | 107.00 |
C2—C7—C6 | 119.14 (14) | C13—C14—H14A | 109.00 |
C6—C7—C8 | 121.64 (15) | C13—C14—H14B | 109.00 |
C2—C7—C8 | 119.21 (14) | C15—C14—H14A | 109.00 |
C7—C8—C9 | 120.62 (15) | C15—C14—H14B | 109.00 |
C8—C9—C10 | 119.49 (14) | H14A—C14—H14B | 108.00 |
O1—C10—C9 | 113.41 (13) | C14—C15—H15A | 110.00 |
C1—C10—C9 | 123.49 (15) | C14—C15—H15B | 110.00 |
O1—C10—C1 | 123.06 (14) | C16—C15—H15A | 110.00 |
C1—C11—C18 | 112.50 (12) | C16—C15—H15B | 110.00 |
C12—C11—C18 | 112.19 (12) | H15A—C15—H15B | 108.00 |
C1—C11—C12 | 109.56 (11) | C15—C16—H16A | 109.00 |
C11—C12—C17 | 122.43 (13) | C15—C16—H16B | 109.00 |
C13—C12—C17 | 119.04 (14) | C17—C16—H16A | 109.00 |
C11—C12—C13 | 118.49 (12) | C17—C16—H16B | 109.00 |
O2—C13—C14 | 121.31 (15) | H16A—C16—H16B | 108.00 |
C12—C13—C14 | 118.09 (13) | C19—C20A—H20A | 110.00 |
O2—C13—C12 | 120.58 (14) | C19—C20A—H20B | 110.00 |
C13—C14—C15 | 112.84 (15) | C21A—C20A—H20A | 110.00 |
C14—C15—C16 | 110.37 (15) | C21A—C20A—H20B | 110.00 |
C15—C16—C17 | 111.34 (15) | H20A—C20A—H20B | 108.00 |
O1—C17—C16 | 111.15 (13) | H20C—C20B—H20D | 108.00 |
C12—C17—C16 | 125.43 (15) | C19—C20B—H20D | 109.00 |
O1—C17—C12 | 123.39 (14) | C21B—C20B—H20C | 109.00 |
C11—C18—C19 | 121.74 (13) | C19—C20B—H20C | 109.00 |
C19—C18—C23 | 119.33 (13) | C21B—C20B—H20D | 109.00 |
C11—C18—C23 | 118.92 (12) | C20A—C21A—H21B | 110.00 |
O3—C19—C18 | 119.12 (14) | C22A—C21A—H21A | 110.00 |
O3—C19—C20A | 116.3 (4) | C20A—C21A—H21A | 110.00 |
C18—C19—C20B | 122.4 (3) | H21A—C21A—H21B | 108.00 |
C18—C19—C20A | 124.3 (4) | C22A—C21A—H21B | 110.00 |
O3—C19—C20B | 118.1 (3) | C20B—C21B—H21D | 110.00 |
C19—C20A—C21A | 108.3 (7) | C20B—C21B—H21C | 110.00 |
C19—C20B—C21B | 112.2 (5) | H21C—C21B—H21D | 108.00 |
C20A—C21A—C22A | 110.0 (6) | C22B—C21B—H21C | 110.00 |
C20B—C21B—C22B | 110.3 (5) | C22B—C21B—H21D | 110.00 |
C21A—C22A—C23 | 113.4 (7) | C23—C22A—H22B | 109.00 |
C21B—C22B—C23 | 111.6 (5) | H22A—C22A—H22B | 108.00 |
C18—C23—C22A | 118.6 (4) | C21A—C22A—H22A | 109.00 |
O4—C23—C22A | 120.8 (4) | C21A—C22A—H22B | 109.00 |
C18—C23—C22B | 120.6 (3) | C23—C22A—H22A | 109.00 |
O4—C23—C18 | 120.38 (14) | C21B—C22B—H22C | 109.00 |
O4—C23—C22B | 118.8 (3) | C21B—C22B—H22D | 109.00 |
C2—C3—H3A | 120.00 | C23—C22B—H22C | 109.00 |
C4—C3—H3A | 119.00 | C23—C22B—H22D | 109.00 |
C3—C4—H4 | 119.00 | H22C—C22B—H22D | 108.00 |
C17—O1—C10—C1 | −12.4 (2) | C18—C11—C12—C13 | −72.26 (16) |
C17—O1—C10—C9 | 165.31 (14) | C18—C11—C12—C17 | 110.02 (16) |
C10—O1—C17—C12 | 11.4 (2) | C1—C11—C18—C19 | −120.34 (15) |
C10—O1—C17—C16 | −166.72 (13) | C1—C11—C18—C23 | 58.68 (17) |
C10—C1—C2—C3 | −179.85 (14) | C12—C11—C18—C19 | 115.59 (15) |
C10—C1—C2—C7 | −0.5 (2) | C12—C11—C18—C23 | −65.40 (17) |
C11—C1—C2—C3 | −0.6 (2) | C11—C12—C13—O2 | 1.1 (2) |
C11—C1—C2—C7 | 178.76 (14) | C11—C12—C13—C14 | −177.18 (14) |
C2—C1—C10—O1 | 177.82 (14) | C17—C12—C13—O2 | 178.93 (15) |
C2—C1—C10—C9 | 0.4 (2) | C17—C12—C13—C14 | 0.6 (2) |
C11—C1—C10—O1 | −1.5 (2) | C11—C12—C17—O1 | 3.6 (2) |
C11—C1—C10—C9 | −178.93 (15) | C11—C12—C17—C16 | −178.61 (15) |
C2—C1—C11—C12 | −164.88 (14) | C13—C12—C17—O1 | −174.15 (14) |
C2—C1—C11—C18 | 69.61 (17) | C13—C12—C17—C16 | 3.7 (2) |
C10—C1—C11—C12 | 14.38 (19) | O2—C13—C14—C15 | 152.03 (16) |
C10—C1—C11—C18 | −111.14 (16) | C12—C13—C14—C15 | −29.7 (2) |
C1—C2—C3—C4 | 179.23 (15) | C13—C14—C15—C16 | 53.5 (2) |
C7—C2—C3—C4 | −0.1 (2) | C14—C15—C16—C17 | −48.5 (2) |
C1—C2—C7—C6 | −178.84 (15) | C15—C16—C17—O1 | −160.62 (14) |
C1—C2—C7—C8 | 0.2 (2) | C15—C16—C17—C12 | 21.3 (2) |
C3—C2—C7—C6 | 0.5 (2) | C11—C18—C19—O3 | 0.9 (2) |
C3—C2—C7—C8 | 179.57 (15) | C11—C18—C19—C20B | 173.9 (4) |
C2—C3—C4—C5 | −0.2 (2) | C23—C18—C19—O3 | −178.09 (14) |
C3—C4—C5—C6 | 0.0 (3) | C23—C18—C19—C20B | −5.1 (5) |
C4—C5—C6—C7 | 0.4 (3) | C11—C18—C23—O4 | 2.7 (2) |
C5—C6—C7—C2 | −0.7 (3) | C11—C18—C23—C22B | −172.0 (4) |
C5—C6—C7—C8 | −179.71 (17) | C19—C18—C23—O4 | −178.22 (14) |
C2—C7—C8—C9 | 0.3 (3) | C19—C18—C23—C22B | 7.0 (4) |
C6—C7—C8—C9 | 179.32 (17) | O3—C19—C20B—C21B | −159.1 (4) |
C7—C8—C9—C10 | −0.5 (3) | C18—C19—C20B—C21B | 27.9 (7) |
C8—C9—C10—O1 | −177.54 (15) | C19—C20B—C21B—C22B | −50.8 (7) |
C8—C9—C10—C1 | 0.1 (3) | C20B—C21B—C22B—C23 | 52.4 (6) |
C1—C11—C12—C13 | 162.05 (13) | C21B—C22B—C23—O4 | 153.7 (4) |
C1—C11—C12—C17 | −15.67 (19) | C21B—C22B—C23—C18 | −31.5 (7) |
Cg3 is the centroid of the C2–C7 benzene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O4i | 0.95 (2) | 1.64 (2) | 2.5793 (15) | 170 (2) |
C3—H3A···O3 | 0.95 | 2.43 | 3.367 (2) | 168 |
C9—H9···O2ii | 0.95 | 2.34 | 3.275 (2) | 170 |
C11—H11···O3 | 1.00 | 2.34 | 2.8228 (17) | 108 |
C14—H14B···Cg3iii | 0.99 | 2.85 | 3.750 (2) | 152 |
Symmetry codes: (i) −x+1/2, y−1/2, z; (ii) −x, y+1/2, −z+1/2; (iii) x−1/2, y, −z+1/2. |
Cg3 is the centroid of the C2–C7 benzene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O4i | 0.95 (2) | 1.64 (2) | 2.5793 (15) | 170 (2) |
C3—H3A···O3 | 0.95 | 2.43 | 3.367 (2) | 168 |
C9—H9···O2ii | 0.95 | 2.34 | 3.275 (2) | 170 |
C14—H14B···Cg3iii | 0.99 | 2.85 | 3.750 (2) | 152 |
Symmetry codes: (i) −x+1/2, y−1/2, z; (ii) −x, y+1/2, −z+1/2; (iii) x−1/2, y, −z+1/2. |
Acknowledgements
AAA thanks the Ministry of Higher Education in Egypt for a grant to support this collaborative project. Manchester Metropolitan University, Erciyes University and University of Strathclyde are gratefully acknowledged for facilitating this study.
References
Abdelhamid, A. A., Mohamed, S. K., Allahverdiyev, M. A., Gurbanov, A. V. & Ng, S. W. (2011). Acta Cryst. E67, o785. Web of Science CSD CrossRef IUCr Journals Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Çelik, Í., Akkurt, M., Jarrahpour, A., Ebrahimi, E. & Büyükgüngör, O. (2009). Acta Cryst. E65, o2522–o2523. Web of Science CSD CrossRef IUCr Journals Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Li, Y.-L., Wang, X.-S., Shi, D.-Q., Tu, S.-J. & Zhang, Y. (2004). Acta Cryst. E60, o1439–o1441. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Menchen, S. M., Benson, S. C., Lam, J. Y. L., Zhen, W., Sun, D., Rosenblum, B. B., Khan, S. H. & Taing, M. (2003a). US Patent, US 6583168. Google Scholar
Menchen, S. M., Benson, S. C., Lam, J. Y. L., Zhen, W., Sun, D., Rosenblum, B. B., Khan, S. H. & Taing, M. (2003b). Chem Abstr. 139, 54287f. Google Scholar
Mohamed, S. K., Abdelhamid, A. A., Khalilov, A. N., Gurbanov, A. V. & Ng, S. W. (2011). Acta Cryst. E67, o850–o851. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Mohamed, S. K., Akkurt, M., Abdelhamid, A. A., Fanwick, P. E. & Potgeiter, H. (2012). Acta Cryst. E68, o1710. CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Reddy, B. P., Vijayakumar, V., Narasimhamurthy, T., Suresh, J. & Lakshman, P. L. N. (2009). Acta Cryst. E65, o916. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sarma, R. J. & Baruah, J. B. (2005). Dyes Pigm. 64, 91–92. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zare, A., Mokhlesi, M., Hasaninejad, A. & Hekmat-Zadehk, T. (2012). E-J. Chem. 9, 1854–1863. CrossRef CAS 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.
Xanthene derivatives have been used as antibacterial, antiviral, antitumor and anti-inflammatory agents (Zare et al., 2012). These compounds also have applications as dyes in laser technology (Menchen et al., 2003a,b), and as pH sensitive fluorescent materials for the visualization of biomolecules (Sarma & Baruah, 2005). Extending our previous studies of xanthenones (Abdelhamid et al., 2011; Mohamed et al., 2011, 2012), we report herein the synthesis and crystal study of a new of xanthenone derivative.
In the title compound shown in Fig. 1, the pyran ring (O1/C1/C10—C12/C17) has a maximum deviation of 0.111 (1) Å from planarity and the outer cyclohexene ring (C12–C17) of the xanthenone moiety is puckered with the puckering parameters (Cremer & Pople, 1975) of Q T = 0.455 (2) Å, θ = 124.4 (2) and ϕ = 352.8 (3)°. The three methylene C atoms (C20/C21/C22) of the other cyclohexene ring attached to the pyran moiety at atom C11 are disordered over two sets of sites with a ratio of refined occupancies of 0.570 (3): 0.430 (3) and both components of the disordered cyclohexene ring are puckered [puckering parameters: Q T = 0.445 (6) Å, θ = 48.7 (6) and ϕ = 183.8 (10)° for major component (C18/C19/C20B–C22B/C23), and Q T = 0.471 (8) Å, θ = 130.2 (8) and ϕ = 353.3 (13)° for minor component (C18/C19/C20A–C22A/C23)].
The bond lengths in the title compound are within normal ranges (Allen et al., 1987) and are comparable those of similar compounds (Li et al., 2004; Abdelhamid et al., 2011; Çelik et al., 2009; Mohamed et al., 2011, 2012; Reddy et al., 2009).
In the crystal structure, C—H···O and O—H···O hydrogen bonds link the neigbouring molecules (Table 1), forming two dimensional networks parallel to the ab-plane (Figs. 2 & 3). A C14—H14B···π interaction also exists between these planes.