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Acta Cryst. (2007). E63, o3493
https://doi.org/10.1107/S1600536807033545
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9-(4-Bromo­phen­yl)-3,3,6,6-tetra­methyl-3,4,6,7-tetra­hydro-2H-xanthene-1,8(5H,9H)-dione

M. A. Bigdeli, G. H. Mahdavinia and V. Amani
The title compound, C23H25BrO3, was synthesized by the reaction of p-bromo­benzaldehyde with dimedone and HClO4/SiO2 in EtOH. In the mol­ecule, the dihydro­pyran ring adopts a boat conformation and the two cyclohexene rings are in a trans conformation.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807033545/lh2439sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807033545/lh2439Isup2.hkl
Contains datablock I

CCDC reference: 657761

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](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
Comment top

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.

Related literature top

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).

Experimental top

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).

Refinement top

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.

Structure description top

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).

Computing details top

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.

Figures top
[Figure 1] Fig. 1. The molecular structure. Displacement ellipsoids are drawn at the 50% probability level
9-(4-Bromophenyl)-3,3,6,6-tetramethyl-3,4,6,7-tetrahydro-2H-xanthene- 1,8(5H,9H)-dione top
Crystal data top
C23H25BrO3F(000) = 888
Mr = 429.34Dx = 1.417 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 475 reflections
a = 5.9667 (6) Åθ = 3–30°
b = 19.5626 (18) ŵ = 2.06 mm−1
c = 17.389 (2) ÅT = 100 K
β = 97.488 (5)°Plate, colourless
V = 2012.5 (4) Å30.30 × 0.25 × 0.25 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		4809 independent reflections
Radiation source: fine-focus sealed tube3885 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
φ and ω scansθmax = 28.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADADS; Sheldrick, 2003)		h = −7→7
Tmin = 0.541, Tmax = 0.596k = −25→11
10510 measured reflectionsl = −22→20
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077H-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 parametersΔρmax = 0.46 e Å−3
0 restraintsΔρmin = −0.36 e Å−3
Crystal data top
C23H25BrO3V = 2012.5 (4) Å3
Mr = 429.34Z = 4
Monoclinic, P21/nMo Kα radiation
a = 5.9667 (6) ŵ = 2.06 mm−1
b = 19.5626 (18) ÅT = 100 K
c = 17.389 (2) Å0.30 × 0.25 × 0.25 mm
β = 97.488 (5)°
Data collection top
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 = 0.596Rint = 0.028
10510 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.077H-atom parameters constrained
S = 1.00Δρmax = 0.46 e Å−3
4809 reflectionsΔρmin = −0.36 e Å−3
248 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br11.07429 (3)0.101879 (10)1.012508 (11)0.02169 (7)
O11.0166 (2)0.30464 (7)0.62322 (8)0.0153 (3)
O20.6944 (2)0.40950 (7)0.82823 (8)0.0226 (3)
O30.3829 (2)0.18458 (7)0.69070 (8)0.0225 (3)
C10.7060 (3)0.28876 (9)0.73700 (10)0.0133 (4)
H1A0.54870.30380.74250.016*
C20.8510 (3)0.35134 (9)0.72954 (11)0.0141 (4)
C30.8399 (3)0.40817 (10)0.78432 (11)0.0166 (4)
C41.0180 (3)0.46320 (10)0.78548 (11)0.0187 (4)
H4A1.15390.44860.82040.022*
H4B0.96030.50540.80740.022*
C51.0877 (3)0.47985 (10)0.70564 (11)0.0153 (4)
C61.1546 (3)0.41280 (9)0.66840 (12)0.0172 (4)
H6A1.16130.42080.61250.021*
H6B1.30780.39940.69250.021*
C70.9954 (3)0.35544 (9)0.67685 (11)0.0139 (4)
C80.8913 (3)0.51453 (10)0.65452 (12)0.0208 (4)
H8A0.85390.55770.67850.031*
H8B0.75900.48440.64920.031*
H8C0.93540.52370.60320.031*
C91.2920 (3)0.52753 (10)0.71582 (12)0.0201 (4)
H9A1.25000.57090.73810.030*
H9B1.34250.53600.66530.030*
H9C1.41480.50620.75060.030*
C100.7008 (3)0.24655 (9)0.66414 (10)0.0132 (4)
C110.5247 (3)0.19420 (10)0.64695 (11)0.0158 (4)
C120.5197 (3)0.15530 (10)0.57155 (11)0.0176 (4)
H12A0.42860.18140.52980.021*
H12B0.44340.11090.57660.021*
C130.7542 (3)0.14199 (10)0.54758 (11)0.0158 (4)
C140.8750 (3)0.21109 (9)0.54547 (11)0.0148 (4)
H14A1.03690.20300.54160.018*
H14B0.81000.23640.49850.018*
C150.8556 (3)0.25385 (9)0.61514 (11)0.0135 (4)
C160.7290 (4)0.11028 (11)0.46627 (12)0.0247 (5)
H16A0.64990.06640.46690.037*
H16B0.87910.10290.45060.037*
H16C0.64210.14120.42940.037*
C170.8883 (3)0.09338 (10)0.60568 (12)0.0208 (4)
H17A0.80890.04950.60580.031*
H17B0.90250.11350.65770.031*
H17C1.03910.08600.59060.031*
C180.7980 (3)0.24673 (9)0.80815 (11)0.0132 (4)
C190.6719 (3)0.23501 (10)0.86853 (11)0.0159 (4)
H19A0.52810.25610.86750.019*
C200.7523 (3)0.19291 (10)0.93060 (11)0.0171 (4)
H20A0.66380.18440.97120.021*
C210.9646 (3)0.16371 (9)0.93175 (10)0.0152 (4)
C221.0978 (3)0.17662 (9)0.87388 (11)0.0150 (4)
H22A1.24490.15750.87650.018*
C231.0130 (3)0.21796 (10)0.81204 (11)0.0153 (4)
H23A1.10260.22680.77180.018*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.02593 (11)0.02092 (11)0.01725 (11)0.00010 (8)−0.00079 (8)0.00554 (8)
O10.0155 (6)0.0123 (6)0.0191 (7)−0.0014 (5)0.0064 (5)−0.0013 (5)
O20.0278 (8)0.0190 (7)0.0232 (8)0.0021 (6)0.0111 (6)−0.0018 (6)
O30.0178 (7)0.0264 (8)0.0252 (8)−0.0045 (6)0.0094 (6)−0.0022 (6)
C10.0123 (8)0.0123 (9)0.0164 (9)0.0015 (7)0.0057 (7)−0.0002 (7)
C20.0144 (9)0.0120 (9)0.0158 (9)0.0016 (7)0.0011 (7)0.0021 (7)
C30.0204 (9)0.0141 (9)0.0152 (9)0.0048 (7)0.0019 (8)0.0026 (7)
C40.0249 (10)0.0158 (9)0.0155 (9)−0.0004 (8)0.0028 (8)−0.0016 (7)
C50.0163 (9)0.0122 (9)0.0171 (9)0.0001 (7)0.0008 (7)0.0008 (7)
C60.0179 (9)0.0151 (9)0.0196 (10)0.0002 (7)0.0057 (8)0.0001 (7)
C70.0150 (9)0.0118 (9)0.0147 (9)0.0033 (7)0.0012 (7)0.0008 (7)
C80.0233 (10)0.0158 (9)0.0226 (10)0.0024 (8)0.0007 (8)0.0028 (8)
C90.0229 (10)0.0144 (9)0.0227 (10)−0.0027 (8)0.0020 (8)−0.0004 (8)
C100.0129 (8)0.0138 (9)0.0129 (9)0.0017 (7)0.0015 (7)0.0017 (7)
C110.0114 (8)0.0176 (9)0.0183 (10)0.0021 (7)0.0013 (7)0.0012 (7)
C120.0126 (9)0.0210 (10)0.0190 (10)−0.0027 (8)0.0014 (7)−0.0026 (8)
C130.0139 (9)0.0166 (9)0.0170 (9)−0.0015 (7)0.0028 (7)−0.0009 (7)
C140.0165 (9)0.0141 (9)0.0143 (9)0.0013 (7)0.0035 (7)0.0015 (7)
C150.0127 (8)0.0115 (9)0.0160 (9)0.0006 (7)0.0006 (7)0.0025 (7)
C160.0257 (11)0.0283 (12)0.0205 (10)−0.0050 (9)0.0043 (8)−0.0098 (9)
C170.0198 (10)0.0173 (10)0.0257 (11)−0.0005 (8)0.0042 (8)0.0012 (8)
C180.0156 (9)0.0100 (8)0.0141 (9)−0.0016 (7)0.0028 (7)−0.0027 (7)
C190.0150 (9)0.0151 (9)0.0183 (10)0.0003 (7)0.0046 (7)−0.0008 (7)
C200.0184 (9)0.0179 (9)0.0164 (9)−0.0020 (8)0.0074 (8)−0.0010 (7)
C210.0215 (9)0.0107 (9)0.0126 (9)−0.0035 (7)−0.0011 (7)−0.0003 (7)
C220.0117 (8)0.0137 (9)0.0193 (9)−0.0002 (7)0.0004 (7)−0.0028 (7)
C230.0159 (9)0.0160 (9)0.0150 (9)−0.0012 (7)0.0054 (7)−0.0006 (7)
Geometric parameters (Å, º) top
Br1—C211.9037 (18)C10—C111.470 (3)
O1—C151.376 (2)C11—C121.513 (3)
O1—C71.380 (2)C12—C131.533 (3)
O2—C31.229 (2)C12—H12A0.9900
O3—C111.224 (2)C12—H12B0.9900
C1—C101.509 (3)C13—C161.533 (3)
C1—C21.514 (3)C13—C171.534 (3)
C1—C181.527 (3)C13—C141.535 (3)
C1—H1A1.0000C14—C151.489 (3)
C2—C71.340 (3)C14—H14A0.9900
C2—C31.471 (3)C14—H14B0.9900
C3—C41.511 (3)C16—H16A0.9800
C4—C51.535 (3)C16—H16B0.9800
C4—H4A0.9900C16—H16C0.9800
C4—H4B0.9900C17—H17A0.9800
C5—C91.527 (3)C17—H17B0.9800
C5—C81.534 (3)C17—H17C0.9800
C5—C61.539 (3)C18—C191.388 (3)
C6—C71.490 (3)C18—C231.394 (3)
C6—H6A0.9900C19—C201.392 (3)
C6—H6B0.9900C19—H19A0.9500
C8—H8A0.9800C20—C211.387 (3)
C8—H8B0.9800C20—H20A0.9500
C8—H8C0.9800C21—C221.385 (3)
C9—H9A0.9800C22—C231.387 (3)
C9—H9B0.9800C22—H22A0.9500
C9—H9C0.9800C23—H23A0.9500
C10—C151.343 (3)
C15—O1—C7117.69 (14)C11—C12—C13113.92 (15)
C10—C1—C2108.65 (15)C11—C12—H12A108.8
C10—C1—C18110.57 (15)C13—C12—H12A108.8
C2—C1—C18110.83 (14)C11—C12—H12B108.8
C10—C1—H1A108.9C13—C12—H12B108.8
C2—C1—H1A108.9H12A—C12—H12B107.7
C18—C1—H1A108.9C12—C13—C16109.65 (15)
C7—C2—C3118.99 (17)C12—C13—C17110.01 (16)
C7—C2—C1122.19 (17)C16—C13—C17109.65 (16)
C3—C2—C1118.76 (16)C12—C13—C14107.77 (16)
O2—C3—C2120.88 (18)C16—C13—C14108.90 (16)
O2—C3—C4121.95 (18)C17—C13—C14110.81 (15)
C2—C3—C4117.15 (17)C15—C14—C13112.87 (16)
C3—C4—C5114.33 (16)C15—C14—H14A109.0
C3—C4—H4A108.7C13—C14—H14A109.0
C5—C4—H4A108.7C15—C14—H14B109.0
C3—C4—H4B108.7C13—C14—H14B109.0
C5—C4—H4B108.7H14A—C14—H14B107.8
H4A—C4—H4B107.6C10—C15—O1122.71 (17)
C9—C5—C8109.59 (16)C10—C15—C14126.09 (17)
C9—C5—C4109.33 (15)O1—C15—C14111.18 (15)
C8—C5—C4109.97 (16)C13—C16—H16A109.5
C9—C5—C6108.81 (15)C13—C16—H16B109.5
C8—C5—C6110.71 (16)H16A—C16—H16B109.5
C4—C5—C6108.40 (15)C13—C16—H16C109.5
C7—C6—C5113.37 (16)H16A—C16—H16C109.5
C7—C6—H6A108.9H16B—C16—H16C109.5
C5—C6—H6A108.9C13—C17—H17A109.5
C7—C6—H6B108.9C13—C17—H17B109.5
C5—C6—H6B108.9H17A—C17—H17B109.5
H6A—C6—H6B107.7C13—C17—H17C109.5
C2—C7—O1122.87 (17)H17A—C17—H17C109.5
C2—C7—C6126.02 (17)H17B—C17—H17C109.5
O1—C7—C6111.10 (16)C19—C18—C23118.85 (17)
C5—C8—H8A109.5C19—C18—C1121.92 (16)
C5—C8—H8B109.5C23—C18—C1119.21 (16)
H8A—C8—H8B109.5C18—C19—C20121.21 (18)
C5—C8—H8C109.5C18—C19—H19A119.4
H8A—C8—H8C109.5C20—C19—H19A119.4
H8B—C8—H8C109.5C21—C20—C19118.45 (18)
C5—C9—H9A109.5C21—C20—H20A120.8
C5—C9—H9B109.5C19—C20—H20A120.8
H9A—C9—H9B109.5C22—C21—C20121.61 (17)
C5—C9—H9C109.5C22—C21—Br1118.50 (14)
H9A—C9—H9C109.5C20—C21—Br1119.86 (14)
H9B—C9—H9C109.5C21—C22—C23118.93 (17)
C15—C10—C11118.52 (17)C21—C22—H22A120.5
C15—C10—C1122.26 (17)C23—C22—H22A120.5
C11—C10—C1119.19 (16)C22—C23—C18120.88 (17)
O3—C11—C10120.96 (18)C22—C23—H23A119.6
O3—C11—C12121.63 (17)C18—C23—H23A119.6
C10—C11—C12117.35 (16)
C10—C1—C2—C7−16.9 (2)C1—C10—C11—C12177.34 (16)
C18—C1—C2—C7104.8 (2)O3—C11—C12—C13−147.91 (18)
C10—C1—C2—C3165.88 (15)C10—C11—C12—C1334.8 (2)
C18—C1—C2—C3−72.4 (2)C11—C12—C13—C16−173.17 (17)
C7—C2—C3—O2172.65 (17)C11—C12—C13—C1766.2 (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—C1546.4 (2)
C1—C2—C3—C4168.34 (16)C16—C13—C14—C15165.24 (16)
O2—C3—C4—C5−145.33 (18)C17—C13—C14—C15−74.1 (2)
C2—C3—C4—C536.3 (2)C11—C10—C15—O1175.09 (16)
C3—C4—C5—C9−171.30 (16)C1—C10—C15—O1−6.7 (3)
C3—C4—C5—C868.3 (2)C11—C10—C15—C14−3.3 (3)
C3—C4—C5—C6−52.8 (2)C1—C10—C15—C14174.92 (17)
C9—C5—C6—C7162.90 (16)C7—O1—C15—C10−9.7 (2)
C8—C5—C6—C7−76.6 (2)C7—O1—C15—C14168.91 (15)
C4—C5—C6—C744.1 (2)C13—C14—C15—C10−19.5 (3)
C3—C2—C7—O1−179.88 (16)C13—C14—C15—O1161.93 (15)
C1—C2—C7—O12.9 (3)C10—C1—C18—C19−120.65 (18)
C3—C2—C7—C61.2 (3)C2—C1—C18—C19118.80 (19)
C1—C2—C7—C6−175.97 (17)C10—C1—C18—C2358.0 (2)
C15—O1—C7—C211.6 (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—C20175.76 (17)
C5—C6—C7—O1160.52 (15)C18—C19—C20—C211.3 (3)
C2—C1—C10—C1518.7 (2)C19—C20—C21—C221.3 (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—C1175.1 (2)Br1—C21—C22—C23175.70 (14)
C15—C10—C11—O3178.39 (18)C21—C22—C23—C180.6 (3)
C1—C10—C11—O30.1 (3)C19—C18—C23—C221.9 (3)
C15—C10—C11—C12−4.3 (2)C1—C18—C23—C22−176.73 (16)

Experimental details

Crystal data
Chemical formulaC23H25BrO3
Mr429.34
Crystal system, space groupMonoclinic, 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)
Z4
Radiation typeMo Kα
µ (mm−1)2.06
Crystal size (mm)0.30 × 0.25 × 0.25
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
Absorption correctionMulti-scan
(SADADS; Sheldrick, 2003)
Tmin, Tmax0.541, 0.596
No. of measured, independent and
observed [I > 2σ(I)] reflections		10510, 4809, 3885
Rint0.028
(sin θ/λ)max (Å−1)0.661
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.077, 1.00
No. of reflections4809
No. of parameters248
H-atom treatmentH-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.

 

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