Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807033545/lh2439sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807033545/lh2439Isup2.hkl |
CCDC reference: 657761
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C)= 0.003 Å
- R factor = 0.031
- wR factor = 0.077
- Data-to-parameter ratio = 19.4
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
A mixture of p-Bromobenzaldehyde (1 mmol), dimedone (2 mmol) and HClO4/SiO2 (20 mg, 0.01 mmol, 1 mol%) was stirred in solvent free condition at 253 K for appropriate time (15 min). The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was dissolved in hot ethanol and the catalyst was separated by simple filtration. The filtrate was kept at room temperature to give the pure product. The milky precipitated product was recrystallized from EtOH. After one day, colorless prismatic crystals were isolated (yield 86%; m.p. 506–508 K).
The H atom positions were calculated [C—H = 0.95–1.00 Å] and they were refined in an isotropic riding-model approximation with Uiso(H) = 1.2Ueq(C) or 1.5 Ueq(C) for methyl groups.
Xanthenes and benzoxanthenes are important classes of compounds that find uses as dyes and fluorescent materials for visualization of bio-molecules and laser technologies due to their useful spectroscopic properties (Menchen et al., 2003). Xanthene-based compounds have also been investigated for agricultural bactericide activity (Hideo, 1981), photodynamic therapy (Ion et al., 2000), anti-inflammatory effect (Poupelin et al., 1987) and antiviral activity (Lambert et al., 1997). Various literature procedures are available to synthesis xanthenes including palladium catalyzed cyclization of polycyclic aryltriflate esters (Wang & Harvey, 2002), intramolecular trapping of benzynes by phenols (Knight & Little, 2001) and reaction of aryloxymagnesium halides with triethylorthoformate (Casiraghi et al., 2003). However, these methodologies suffer from one or more disadvantages such as low yield, lack of easy availability or preparation of the starting materials, prolonged reaction time (16 h to 5 days), use of toxic organic solvents, requirement of excess of reagents or catalysts, special apparatus and harsh reaction conditions. In the light of the above, we have synthesized the title compound.
The bond lengths and angles in the title molecule (Fig. 1) are comparable with those reported for related structures (Tu et al., 2002; Jeyakanthan et al., 1999; Li et al., 2005; Shi et al., 1997; Tu et al., 2004). The pyran rings have a half-chair conformations; atoms C5 and C13 lie 0.471Å and 0.533Å from the mean plane through atoms C6/C7/C2/C3 and C14/C15/C10/C11 respectively, while atoms C4 and C12 are only 0.189Å and 0.158 Å from these planes. The dihedral angles between the benzene ring of the bromo-phenyl group the main planes of the pyran rings are 78.67 (16)° and 87.33 (18)° for C2—C7 and C10—C15 respectively.
For related crystal structures, see: Tu et al. (2002, 2004); Jeyakanthan et al. (1999); Li et al. (2005); Shi et al. (1997). For related literature, see: Casiraghi et al. (2003); Hideo (1981); Ion et al. (2000); Knight & Little (2001); Lambert et al. (1997); Menchen et al. (2003); Poupelin et al. (1987); Wang & Harvey (2002).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Fig. 1. The molecular structure. Displacement ellipsoids are drawn at the 50% probability level |
C23H25BrO3 | F(000) = 888 |
Mr = 429.34 | Dx = 1.417 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 475 reflections |
a = 5.9667 (6) Å | θ = 3–30° |
b = 19.5626 (18) Å | µ = 2.06 mm−1 |
c = 17.389 (2) Å | T = 100 K |
β = 97.488 (5)° | Plate, colourless |
V = 2012.5 (4) Å3 | 0.30 × 0.25 × 0.25 mm |
Z = 4 |
Bruker SMART APEXII CCD area-detector diffractometer | 4809 independent reflections |
Radiation source: fine-focus sealed tube | 3885 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
φ and ω scans | θmax = 28.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADADS; Sheldrick, 2003) | h = −7→7 |
Tmin = 0.541, Tmax = 0.596 | k = −25→11 |
10510 measured reflections | l = −22→20 |
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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.077 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.039P)2 + 0.432P] where P = (Fo2 + 2Fc2)/3 |
4809 reflections | (Δ/σ)max = 0.001 |
248 parameters | Δρmax = 0.46 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
C23H25BrO3 | V = 2012.5 (4) Å3 |
Mr = 429.34 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 5.9667 (6) Å | µ = 2.06 mm−1 |
b = 19.5626 (18) Å | T = 100 K |
c = 17.389 (2) Å | 0.30 × 0.25 × 0.25 mm |
β = 97.488 (5)° |
Bruker SMART APEXII CCD area-detector diffractometer | 4809 independent reflections |
Absorption correction: multi-scan (SADADS; Sheldrick, 2003) | 3885 reflections with I > 2σ(I) |
Tmin = 0.541, Tmax = 0.596 | Rint = 0.028 |
10510 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.077 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.46 e Å−3 |
4809 reflections | Δρmin = −0.36 e Å−3 |
248 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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 1.07429 (3) | 0.101879 (10) | 1.012508 (11) | 0.02169 (7) | |
O1 | 1.0166 (2) | 0.30464 (7) | 0.62322 (8) | 0.0153 (3) | |
O2 | 0.6944 (2) | 0.40950 (7) | 0.82823 (8) | 0.0226 (3) | |
O3 | 0.3829 (2) | 0.18458 (7) | 0.69070 (8) | 0.0225 (3) | |
C1 | 0.7060 (3) | 0.28876 (9) | 0.73700 (10) | 0.0133 (4) | |
H1A | 0.5487 | 0.3038 | 0.7425 | 0.016* | |
C2 | 0.8510 (3) | 0.35134 (9) | 0.72954 (11) | 0.0141 (4) | |
C3 | 0.8399 (3) | 0.40817 (10) | 0.78432 (11) | 0.0166 (4) | |
C4 | 1.0180 (3) | 0.46320 (10) | 0.78548 (11) | 0.0187 (4) | |
H4A | 1.1539 | 0.4486 | 0.8204 | 0.022* | |
H4B | 0.9603 | 0.5054 | 0.8074 | 0.022* | |
C5 | 1.0877 (3) | 0.47985 (10) | 0.70564 (11) | 0.0153 (4) | |
C6 | 1.1546 (3) | 0.41280 (9) | 0.66840 (12) | 0.0172 (4) | |
H6A | 1.1613 | 0.4208 | 0.6125 | 0.021* | |
H6B | 1.3078 | 0.3994 | 0.6925 | 0.021* | |
C7 | 0.9954 (3) | 0.35544 (9) | 0.67685 (11) | 0.0139 (4) | |
C8 | 0.8913 (3) | 0.51453 (10) | 0.65452 (12) | 0.0208 (4) | |
H8A | 0.8539 | 0.5577 | 0.6785 | 0.031* | |
H8B | 0.7590 | 0.4844 | 0.6492 | 0.031* | |
H8C | 0.9354 | 0.5237 | 0.6032 | 0.031* | |
C9 | 1.2920 (3) | 0.52753 (10) | 0.71582 (12) | 0.0201 (4) | |
H9A | 1.2500 | 0.5709 | 0.7381 | 0.030* | |
H9B | 1.3425 | 0.5360 | 0.6653 | 0.030* | |
H9C | 1.4148 | 0.5062 | 0.7506 | 0.030* | |
C10 | 0.7008 (3) | 0.24655 (9) | 0.66414 (10) | 0.0132 (4) | |
C11 | 0.5247 (3) | 0.19420 (10) | 0.64695 (11) | 0.0158 (4) | |
C12 | 0.5197 (3) | 0.15530 (10) | 0.57155 (11) | 0.0176 (4) | |
H12A | 0.4286 | 0.1814 | 0.5298 | 0.021* | |
H12B | 0.4434 | 0.1109 | 0.5766 | 0.021* | |
C13 | 0.7542 (3) | 0.14199 (10) | 0.54758 (11) | 0.0158 (4) | |
C14 | 0.8750 (3) | 0.21109 (9) | 0.54547 (11) | 0.0148 (4) | |
H14A | 1.0369 | 0.2030 | 0.5416 | 0.018* | |
H14B | 0.8100 | 0.2364 | 0.4985 | 0.018* | |
C15 | 0.8556 (3) | 0.25385 (9) | 0.61514 (11) | 0.0135 (4) | |
C16 | 0.7290 (4) | 0.11028 (11) | 0.46627 (12) | 0.0247 (5) | |
H16A | 0.6499 | 0.0664 | 0.4669 | 0.037* | |
H16B | 0.8791 | 0.1029 | 0.4506 | 0.037* | |
H16C | 0.6421 | 0.1412 | 0.4294 | 0.037* | |
C17 | 0.8883 (3) | 0.09338 (10) | 0.60568 (12) | 0.0208 (4) | |
H17A | 0.8089 | 0.0495 | 0.6058 | 0.031* | |
H17B | 0.9025 | 0.1135 | 0.6577 | 0.031* | |
H17C | 1.0391 | 0.0860 | 0.5906 | 0.031* | |
C18 | 0.7980 (3) | 0.24673 (9) | 0.80815 (11) | 0.0132 (4) | |
C19 | 0.6719 (3) | 0.23501 (10) | 0.86853 (11) | 0.0159 (4) | |
H19A | 0.5281 | 0.2561 | 0.8675 | 0.019* | |
C20 | 0.7523 (3) | 0.19291 (10) | 0.93060 (11) | 0.0171 (4) | |
H20A | 0.6638 | 0.1844 | 0.9712 | 0.021* | |
C21 | 0.9646 (3) | 0.16371 (9) | 0.93175 (10) | 0.0152 (4) | |
C22 | 1.0978 (3) | 0.17662 (9) | 0.87388 (11) | 0.0150 (4) | |
H22A | 1.2449 | 0.1575 | 0.8765 | 0.018* | |
C23 | 1.0130 (3) | 0.21796 (10) | 0.81204 (11) | 0.0153 (4) | |
H23A | 1.1026 | 0.2268 | 0.7718 | 0.018* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.02593 (11) | 0.02092 (11) | 0.01725 (11) | 0.00010 (8) | −0.00079 (8) | 0.00554 (8) |
O1 | 0.0155 (6) | 0.0123 (6) | 0.0191 (7) | −0.0014 (5) | 0.0064 (5) | −0.0013 (5) |
O2 | 0.0278 (8) | 0.0190 (7) | 0.0232 (8) | 0.0021 (6) | 0.0111 (6) | −0.0018 (6) |
O3 | 0.0178 (7) | 0.0264 (8) | 0.0252 (8) | −0.0045 (6) | 0.0094 (6) | −0.0022 (6) |
C1 | 0.0123 (8) | 0.0123 (9) | 0.0164 (9) | 0.0015 (7) | 0.0057 (7) | −0.0002 (7) |
C2 | 0.0144 (9) | 0.0120 (9) | 0.0158 (9) | 0.0016 (7) | 0.0011 (7) | 0.0021 (7) |
C3 | 0.0204 (9) | 0.0141 (9) | 0.0152 (9) | 0.0048 (7) | 0.0019 (8) | 0.0026 (7) |
C4 | 0.0249 (10) | 0.0158 (9) | 0.0155 (9) | −0.0004 (8) | 0.0028 (8) | −0.0016 (7) |
C5 | 0.0163 (9) | 0.0122 (9) | 0.0171 (9) | 0.0001 (7) | 0.0008 (7) | 0.0008 (7) |
C6 | 0.0179 (9) | 0.0151 (9) | 0.0196 (10) | 0.0002 (7) | 0.0057 (8) | 0.0001 (7) |
C7 | 0.0150 (9) | 0.0118 (9) | 0.0147 (9) | 0.0033 (7) | 0.0012 (7) | 0.0008 (7) |
C8 | 0.0233 (10) | 0.0158 (9) | 0.0226 (10) | 0.0024 (8) | 0.0007 (8) | 0.0028 (8) |
C9 | 0.0229 (10) | 0.0144 (9) | 0.0227 (10) | −0.0027 (8) | 0.0020 (8) | −0.0004 (8) |
C10 | 0.0129 (8) | 0.0138 (9) | 0.0129 (9) | 0.0017 (7) | 0.0015 (7) | 0.0017 (7) |
C11 | 0.0114 (8) | 0.0176 (9) | 0.0183 (10) | 0.0021 (7) | 0.0013 (7) | 0.0012 (7) |
C12 | 0.0126 (9) | 0.0210 (10) | 0.0190 (10) | −0.0027 (8) | 0.0014 (7) | −0.0026 (8) |
C13 | 0.0139 (9) | 0.0166 (9) | 0.0170 (9) | −0.0015 (7) | 0.0028 (7) | −0.0009 (7) |
C14 | 0.0165 (9) | 0.0141 (9) | 0.0143 (9) | 0.0013 (7) | 0.0035 (7) | 0.0015 (7) |
C15 | 0.0127 (8) | 0.0115 (9) | 0.0160 (9) | 0.0006 (7) | 0.0006 (7) | 0.0025 (7) |
C16 | 0.0257 (11) | 0.0283 (12) | 0.0205 (10) | −0.0050 (9) | 0.0043 (8) | −0.0098 (9) |
C17 | 0.0198 (10) | 0.0173 (10) | 0.0257 (11) | −0.0005 (8) | 0.0042 (8) | 0.0012 (8) |
C18 | 0.0156 (9) | 0.0100 (8) | 0.0141 (9) | −0.0016 (7) | 0.0028 (7) | −0.0027 (7) |
C19 | 0.0150 (9) | 0.0151 (9) | 0.0183 (10) | 0.0003 (7) | 0.0046 (7) | −0.0008 (7) |
C20 | 0.0184 (9) | 0.0179 (9) | 0.0164 (9) | −0.0020 (8) | 0.0074 (8) | −0.0010 (7) |
C21 | 0.0215 (9) | 0.0107 (9) | 0.0126 (9) | −0.0035 (7) | −0.0011 (7) | −0.0003 (7) |
C22 | 0.0117 (8) | 0.0137 (9) | 0.0193 (9) | −0.0002 (7) | 0.0004 (7) | −0.0028 (7) |
C23 | 0.0159 (9) | 0.0160 (9) | 0.0150 (9) | −0.0012 (7) | 0.0054 (7) | −0.0006 (7) |
Br1—C21 | 1.9037 (18) | C10—C11 | 1.470 (3) |
O1—C15 | 1.376 (2) | C11—C12 | 1.513 (3) |
O1—C7 | 1.380 (2) | C12—C13 | 1.533 (3) |
O2—C3 | 1.229 (2) | C12—H12A | 0.9900 |
O3—C11 | 1.224 (2) | C12—H12B | 0.9900 |
C1—C10 | 1.509 (3) | C13—C16 | 1.533 (3) |
C1—C2 | 1.514 (3) | C13—C17 | 1.534 (3) |
C1—C18 | 1.527 (3) | C13—C14 | 1.535 (3) |
C1—H1A | 1.0000 | C14—C15 | 1.489 (3) |
C2—C7 | 1.340 (3) | C14—H14A | 0.9900 |
C2—C3 | 1.471 (3) | C14—H14B | 0.9900 |
C3—C4 | 1.511 (3) | C16—H16A | 0.9800 |
C4—C5 | 1.535 (3) | C16—H16B | 0.9800 |
C4—H4A | 0.9900 | C16—H16C | 0.9800 |
C4—H4B | 0.9900 | C17—H17A | 0.9800 |
C5—C9 | 1.527 (3) | C17—H17B | 0.9800 |
C5—C8 | 1.534 (3) | C17—H17C | 0.9800 |
C5—C6 | 1.539 (3) | C18—C19 | 1.388 (3) |
C6—C7 | 1.490 (3) | C18—C23 | 1.394 (3) |
C6—H6A | 0.9900 | C19—C20 | 1.392 (3) |
C6—H6B | 0.9900 | C19—H19A | 0.9500 |
C8—H8A | 0.9800 | C20—C21 | 1.387 (3) |
C8—H8B | 0.9800 | C20—H20A | 0.9500 |
C8—H8C | 0.9800 | C21—C22 | 1.385 (3) |
C9—H9A | 0.9800 | C22—C23 | 1.387 (3) |
C9—H9B | 0.9800 | C22—H22A | 0.9500 |
C9—H9C | 0.9800 | C23—H23A | 0.9500 |
C10—C15 | 1.343 (3) | ||
C15—O1—C7 | 117.69 (14) | C11—C12—C13 | 113.92 (15) |
C10—C1—C2 | 108.65 (15) | C11—C12—H12A | 108.8 |
C10—C1—C18 | 110.57 (15) | C13—C12—H12A | 108.8 |
C2—C1—C18 | 110.83 (14) | C11—C12—H12B | 108.8 |
C10—C1—H1A | 108.9 | C13—C12—H12B | 108.8 |
C2—C1—H1A | 108.9 | H12A—C12—H12B | 107.7 |
C18—C1—H1A | 108.9 | C12—C13—C16 | 109.65 (15) |
C7—C2—C3 | 118.99 (17) | C12—C13—C17 | 110.01 (16) |
C7—C2—C1 | 122.19 (17) | C16—C13—C17 | 109.65 (16) |
C3—C2—C1 | 118.76 (16) | C12—C13—C14 | 107.77 (16) |
O2—C3—C2 | 120.88 (18) | C16—C13—C14 | 108.90 (16) |
O2—C3—C4 | 121.95 (18) | C17—C13—C14 | 110.81 (15) |
C2—C3—C4 | 117.15 (17) | C15—C14—C13 | 112.87 (16) |
C3—C4—C5 | 114.33 (16) | C15—C14—H14A | 109.0 |
C3—C4—H4A | 108.7 | C13—C14—H14A | 109.0 |
C5—C4—H4A | 108.7 | C15—C14—H14B | 109.0 |
C3—C4—H4B | 108.7 | C13—C14—H14B | 109.0 |
C5—C4—H4B | 108.7 | H14A—C14—H14B | 107.8 |
H4A—C4—H4B | 107.6 | C10—C15—O1 | 122.71 (17) |
C9—C5—C8 | 109.59 (16) | C10—C15—C14 | 126.09 (17) |
C9—C5—C4 | 109.33 (15) | O1—C15—C14 | 111.18 (15) |
C8—C5—C4 | 109.97 (16) | C13—C16—H16A | 109.5 |
C9—C5—C6 | 108.81 (15) | C13—C16—H16B | 109.5 |
C8—C5—C6 | 110.71 (16) | H16A—C16—H16B | 109.5 |
C4—C5—C6 | 108.40 (15) | C13—C16—H16C | 109.5 |
C7—C6—C5 | 113.37 (16) | H16A—C16—H16C | 109.5 |
C7—C6—H6A | 108.9 | H16B—C16—H16C | 109.5 |
C5—C6—H6A | 108.9 | C13—C17—H17A | 109.5 |
C7—C6—H6B | 108.9 | C13—C17—H17B | 109.5 |
C5—C6—H6B | 108.9 | H17A—C17—H17B | 109.5 |
H6A—C6—H6B | 107.7 | C13—C17—H17C | 109.5 |
C2—C7—O1 | 122.87 (17) | H17A—C17—H17C | 109.5 |
C2—C7—C6 | 126.02 (17) | H17B—C17—H17C | 109.5 |
O1—C7—C6 | 111.10 (16) | C19—C18—C23 | 118.85 (17) |
C5—C8—H8A | 109.5 | C19—C18—C1 | 121.92 (16) |
C5—C8—H8B | 109.5 | C23—C18—C1 | 119.21 (16) |
H8A—C8—H8B | 109.5 | C18—C19—C20 | 121.21 (18) |
C5—C8—H8C | 109.5 | C18—C19—H19A | 119.4 |
H8A—C8—H8C | 109.5 | C20—C19—H19A | 119.4 |
H8B—C8—H8C | 109.5 | C21—C20—C19 | 118.45 (18) |
C5—C9—H9A | 109.5 | C21—C20—H20A | 120.8 |
C5—C9—H9B | 109.5 | C19—C20—H20A | 120.8 |
H9A—C9—H9B | 109.5 | C22—C21—C20 | 121.61 (17) |
C5—C9—H9C | 109.5 | C22—C21—Br1 | 118.50 (14) |
H9A—C9—H9C | 109.5 | C20—C21—Br1 | 119.86 (14) |
H9B—C9—H9C | 109.5 | C21—C22—C23 | 118.93 (17) |
C15—C10—C11 | 118.52 (17) | C21—C22—H22A | 120.5 |
C15—C10—C1 | 122.26 (17) | C23—C22—H22A | 120.5 |
C11—C10—C1 | 119.19 (16) | C22—C23—C18 | 120.88 (17) |
O3—C11—C10 | 120.96 (18) | C22—C23—H23A | 119.6 |
O3—C11—C12 | 121.63 (17) | C18—C23—H23A | 119.6 |
C10—C11—C12 | 117.35 (16) | ||
C10—C1—C2—C7 | −16.9 (2) | C1—C10—C11—C12 | 177.34 (16) |
C18—C1—C2—C7 | 104.8 (2) | O3—C11—C12—C13 | −147.91 (18) |
C10—C1—C2—C3 | 165.88 (15) | C10—C11—C12—C13 | 34.8 (2) |
C18—C1—C2—C3 | −72.4 (2) | C11—C12—C13—C16 | −173.17 (17) |
C7—C2—C3—O2 | 172.65 (17) | C11—C12—C13—C17 | 66.2 (2) |
C1—C2—C3—O2 | −10.1 (3) | C11—C12—C13—C14 | −54.8 (2) |
C7—C2—C3—C4 | −9.0 (2) | C12—C13—C14—C15 | 46.4 (2) |
C1—C2—C3—C4 | 168.34 (16) | C16—C13—C14—C15 | 165.24 (16) |
O2—C3—C4—C5 | −145.33 (18) | C17—C13—C14—C15 | −74.1 (2) |
C2—C3—C4—C5 | 36.3 (2) | C11—C10—C15—O1 | 175.09 (16) |
C3—C4—C5—C9 | −171.30 (16) | C1—C10—C15—O1 | −6.7 (3) |
C3—C4—C5—C8 | 68.3 (2) | C11—C10—C15—C14 | −3.3 (3) |
C3—C4—C5—C6 | −52.8 (2) | C1—C10—C15—C14 | 174.92 (17) |
C9—C5—C6—C7 | 162.90 (16) | C7—O1—C15—C10 | −9.7 (2) |
C8—C5—C6—C7 | −76.6 (2) | C7—O1—C15—C14 | 168.91 (15) |
C4—C5—C6—C7 | 44.1 (2) | C13—C14—C15—C10 | −19.5 (3) |
C3—C2—C7—O1 | −179.88 (16) | C13—C14—C15—O1 | 161.93 (15) |
C1—C2—C7—O1 | 2.9 (3) | C10—C1—C18—C19 | −120.65 (18) |
C3—C2—C7—C6 | 1.2 (3) | C2—C1—C18—C19 | 118.80 (19) |
C1—C2—C7—C6 | −175.97 (17) | C10—C1—C18—C23 | 58.0 (2) |
C15—O1—C7—C2 | 11.6 (2) | C2—C1—C18—C23 | −62.6 (2) |
C15—O1—C7—C6 | −169.34 (15) | C23—C18—C19—C20 | −2.8 (3) |
C5—C6—C7—C2 | −20.5 (3) | C1—C18—C19—C20 | 175.76 (17) |
C5—C6—C7—O1 | 160.52 (15) | C18—C19—C20—C21 | 1.3 (3) |
C2—C1—C10—C15 | 18.7 (2) | C19—C20—C21—C22 | 1.3 (3) |
C18—C1—C10—C15 | −103.1 (2) | C19—C20—C21—Br1 | −176.57 (14) |
C2—C1—C10—C11 | −163.02 (15) | C20—C21—C22—C23 | −2.2 (3) |
C18—C1—C10—C11 | 75.1 (2) | Br1—C21—C22—C23 | 175.70 (14) |
C15—C10—C11—O3 | 178.39 (18) | C21—C22—C23—C18 | 0.6 (3) |
C1—C10—C11—O3 | 0.1 (3) | C19—C18—C23—C22 | 1.9 (3) |
C15—C10—C11—C12 | −4.3 (2) | C1—C18—C23—C22 | −176.73 (16) |
Experimental details
Crystal data | |
Chemical formula | C23H25BrO3 |
Mr | 429.34 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 100 |
a, b, c (Å) | 5.9667 (6), 19.5626 (18), 17.389 (2) |
β (°) | 97.488 (5) |
V (Å3) | 2012.5 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.06 |
Crystal size (mm) | 0.30 × 0.25 × 0.25 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector |
Absorption correction | Multi-scan (SADADS; Sheldrick, 2003) |
Tmin, Tmax | 0.541, 0.596 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10510, 4809, 3885 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.661 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.077, 1.00 |
No. of reflections | 4809 |
No. of parameters | 248 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.46, −0.36 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2001), SAINT, SHELXTL (Sheldrick, 1998), SHELXTL.
Xanthenes and benzoxanthenes are important classes of compounds that find uses as dyes and fluorescent materials for visualization of bio-molecules and laser technologies due to their useful spectroscopic properties (Menchen et al., 2003). Xanthene-based compounds have also been investigated for agricultural bactericide activity (Hideo, 1981), photodynamic therapy (Ion et al., 2000), anti-inflammatory effect (Poupelin et al., 1987) and antiviral activity (Lambert et al., 1997). Various literature procedures are available to synthesis xanthenes including palladium catalyzed cyclization of polycyclic aryltriflate esters (Wang & Harvey, 2002), intramolecular trapping of benzynes by phenols (Knight & Little, 2001) and reaction of aryloxymagnesium halides with triethylorthoformate (Casiraghi et al., 2003). However, these methodologies suffer from one or more disadvantages such as low yield, lack of easy availability or preparation of the starting materials, prolonged reaction time (16 h to 5 days), use of toxic organic solvents, requirement of excess of reagents or catalysts, special apparatus and harsh reaction conditions. In the light of the above, we have synthesized the title compound.
The bond lengths and angles in the title molecule (Fig. 1) are comparable with those reported for related structures (Tu et al., 2002; Jeyakanthan et al., 1999; Li et al., 2005; Shi et al., 1997; Tu et al., 2004). The pyran rings have a half-chair conformations; atoms C5 and C13 lie 0.471Å and 0.533Å from the mean plane through atoms C6/C7/C2/C3 and C14/C15/C10/C11 respectively, while atoms C4 and C12 are only 0.189Å and 0.158 Å from these planes. The dihedral angles between the benzene ring of the bromo-phenyl group the main planes of the pyran rings are 78.67 (16)° and 87.33 (18)° for C2—C7 and C10—C15 respectively.