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Acta Cryst. (2007). E63, o4148
https://doi.org/10.1107/S1600536807045576
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rac-Diethyl [(1S,2R)-1-(4-bromo­phen­yl)-6-hydr­oxy-3-oxo-2,3-dihydro-1H-benzo[f]chromen-2-yl]phospho­nate

H. Krawczyk, Ł. Albrecht, J. Wojciechowski and W. M. Wolf
In the title compound, C23H22BrO6P, the δ-valerolactone ring adopts a distorted screw-boat conformation, with the diethoxy­phosphoryl substituent occupying an axial position. An unusual eclipsed conformation is found for the P—C bond. The mol­ecules form centrosymmetric dimers connected by O—H...O hydrogen bonds. One of the methyl groups is disordered, with site occupancies of ca 0.8:0.2.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045576/bt2512sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045576/bt2512Isup2.hkl
Contains datablock I

CCDC reference: 663827

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 90 K
  • Mean [sigma](C-C) = 0.002 Å
  • Disorder in main residue
  • R factor = 0.023
  • wR factor = 0.064
  • Data-to-parameter ratio = 18.3

checkCIF/PLATON results

No syntax errors found




Alert level A
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.31 Ratio
Author Response: This problem follow from the disorder detected in the dietoxyphosphoryl substituent. The disordered H's have higher U's than remaining well defined H's atoms. X-ray data were collected at 90 K, the final R for all reflections is 0.026. The structure refinement was stable and all H's (including those disordered) were localized on a difference Fourier maps. 

Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.67 Ratio


Alert level C
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct...         11
PLAT301_ALERT_3_C Main Residue  Disorder .........................       3.00 Perc.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br     ..  O1      ..       3.18 Ang.


Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C2     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C3     = ...          S


   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check
Comment top

Neoflavonoids show a wide range of biological activities (Bailly et al., 2003; Zhang et al., 2006; Roelens et al., 2005). The title compound is a key product in the novel synthesis of 4-aryl-3,4-dihydrocoumarins based on CF3SO3H promoted Friedel Crafts reaction of electron-rich hydroxyarenes with the acids bearing electron-withdrawing substituents on the aromatic ring (Krawczyk et al., 2007). A view of (I), with atom numbering scheme is shown in Fig. 1. The δ-valerolactone and naphthalene moieties are almost coplanar with one another. The former ring adopts conformation close to a 4S3 screw-boat (Boeyens, 1978), with O1, C1, C3, C4 and C9 almost coplanar (the average r.m.s. deviation from the mean plane is 0.05 Å) and C2 situated at the flap. The Cremer & Pople (1975) puckering parameters for the ring atom sequence O1/C1/C2/C3/C4/C9 are: Q = 0.48 (2) Å, θ = 116.6 (2) and φ = 315.84 (2)°. Both exocyclic substituents, namely the diethoxyphosphoryl and phenyl groups occupy axial positions in respect to the δ-valerolactone ring. The former adopts unusual eclipsed conformation when looking along the C2—P bond (Fig. 2). This particular arrangement is locked by either Coulombic attraction between phosphoryl O4 and carbonyl C1 or the C—H···π(naphthalene) interactions [H223···C5 2.89 (2) Å]. In the crystal molecules form centrosymmetric dimers connected by strong hydrogen bonds linking phosphoryl and hydroxyl groups of both monomers. In terms of Etter's graph-set terminology (Etter, 1990; Bernstein et al., 1995) this system can be described as R22(20). The Br atom is involved in a short contact [3.183 (1) Å] with the endocyclic O1 atom of the neighbouring [0.5 - x, y - 0.5, 0.5 - z] molecule.

Related literature top

For related literature, see: Bernstein et al. (1995); Boeyens (1978); Cremer & Pople (1975); Etter (1990); Krawczyk et al. (2007). For biologically active 4-aryl-3,4-dihydrocoumarins, see: Bailly et al. (2003; Zhang et al. (2006); Roelens et al. (2005).

Experimental top

The CF3SO3H promoted Friedel Crafts reaction of electron-rich hydroxyarenes with the acids bearing electron-withdrawing substituents on the aromatic ring. Details of the synthesis are published elsewhere (Krawczyk et al., 2007). Good quality single crystals were obtained from the ethyl ether solution.

Refinement top

The C23 atom of the diethoxyphosphoryl group displayed conformational disorder and was refined in a two-site disorder model. The occupancy of the major component refined to a value of 0.825 (5). H atoms were located on a difference Fourier maps calculated during the anisotropic refinement. H atoms of the diethoxyphosphoryl group were refined as riding on their parent C atoms. Positional and isotropic displacement parameters of the remaining H's were allowed to refine freely.

Structure description top

Neoflavonoids show a wide range of biological activities (Bailly et al., 2003; Zhang et al., 2006; Roelens et al., 2005). The title compound is a key product in the novel synthesis of 4-aryl-3,4-dihydrocoumarins based on CF3SO3H promoted Friedel Crafts reaction of electron-rich hydroxyarenes with the acids bearing electron-withdrawing substituents on the aromatic ring (Krawczyk et al., 2007). A view of (I), with atom numbering scheme is shown in Fig. 1. The δ-valerolactone and naphthalene moieties are almost coplanar with one another. The former ring adopts conformation close to a 4S3 screw-boat (Boeyens, 1978), with O1, C1, C3, C4 and C9 almost coplanar (the average r.m.s. deviation from the mean plane is 0.05 Å) and C2 situated at the flap. The Cremer & Pople (1975) puckering parameters for the ring atom sequence O1/C1/C2/C3/C4/C9 are: Q = 0.48 (2) Å, θ = 116.6 (2) and φ = 315.84 (2)°. Both exocyclic substituents, namely the diethoxyphosphoryl and phenyl groups occupy axial positions in respect to the δ-valerolactone ring. The former adopts unusual eclipsed conformation when looking along the C2—P bond (Fig. 2). This particular arrangement is locked by either Coulombic attraction between phosphoryl O4 and carbonyl C1 or the C—H···π(naphthalene) interactions [H223···C5 2.89 (2) Å]. In the crystal molecules form centrosymmetric dimers connected by strong hydrogen bonds linking phosphoryl and hydroxyl groups of both monomers. In terms of Etter's graph-set terminology (Etter, 1990; Bernstein et al., 1995) this system can be described as R22(20). The Br atom is involved in a short contact [3.183 (1) Å] with the endocyclic O1 atom of the neighbouring [0.5 - x, y - 0.5, 0.5 - z] molecule.

For related literature, see: Bernstein et al. (1995); Boeyens (1978); Cremer & Pople (1975); Etter (1990); Krawczyk et al. (2007). For biologically active 4-aryl-3,4-dihydrocoumarins, see: Bailly et al. (2003; Zhang et al. (2006); Roelens et al. (2005).

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXTL (Bruker, 2003); program(s) used to refine structure: SHELXTL (Bruker, 2003); molecular graphics: SHELXTL (Bruker, 2003); software used to prepare material for publication: SHELXTL (Bruker, 2003).

Figures top
[Figure 1] Fig. 1. View of the molecule. Displacement elipsoids are drawn at the 50% probability level. The C23 methyl group is disordered and was refined over two sites. The picture shows sites for which the occupation factor was 0.825 (5).
[Figure 2] Fig. 2. Newman projection along the C2—P bond.
rac-Diethyl [(1S,2R)-1-(4-bromophenyl)-6-hydroxy-3-oxo-2,3-dihydro-1H- benzo[f]chromen-2-yl]phosphonate top
Crystal data top
C23H22BrO6PF(000) = 1032
Mr = 505.29Dx = 1.407 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 12.8328 (5) ÅCell parameters from 7599 reflections
b = 11.7500 (5) Åθ = 2.2–31.1°
c = 15.8477 (7) ŵ = 1.83 mm−1
β = 93.184 (1)°T = 90 K
V = 2385.91 (17) Å3Prism, colourless
Z = 40.20 × 0.20 × 0.10 mm
Data collection top
Bruker SMART APEX
diffractometer		6239 independent reflections
Radiation source: fine-focus sealed tube5698 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ω scansθmax = 29.0°, θmin = 2.0°
Absorption correction: multi-scan
(SHELXTL; Bruker, 2003)		h = −16→17
Tmin = 0.697, Tmax = 0.839k = −15→15
54317 measured reflectionsl = −21→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)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.064H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0365P)2 + 0.8812P]
where P = (Fo2 + 2Fc2)/3
6239 reflections(Δ/σ)max = 0.001
341 parametersΔρmax = 0.43 e Å−3
0 restraintsΔρmin = −0.38 e Å−3
Crystal data top
C23H22BrO6PV = 2385.91 (17) Å3
Mr = 505.29Z = 4
Monoclinic, P21/nMo Kα radiation
a = 12.8328 (5) ŵ = 1.83 mm−1
b = 11.7500 (5) ÅT = 90 K
c = 15.8477 (7) Å0.20 × 0.20 × 0.10 mm
β = 93.184 (1)°
Data collection top
Bruker SMART APEX
diffractometer		6239 independent reflections
Absorption correction: multi-scan
(SHELXTL; Bruker, 2003)		5698 reflections with I > 2σ(I)
Tmin = 0.697, Tmax = 0.839Rint = 0.021
54317 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0230 restraints
wR(F2) = 0.064H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.43 e Å−3
6239 reflectionsΔρmin = −0.38 e Å−3
341 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*/UeqOcc. (<1)
Br0.284650 (10)−0.133212 (11)0.117426 (9)0.02620 (5)
P0.67307 (2)0.19775 (2)0.525826 (18)0.01323 (6)
O10.44301 (6)0.30270 (7)0.45792 (5)0.01483 (16)
O20.40612 (7)0.14418 (7)0.52698 (6)0.01900 (17)
O30.71414 (6)0.08202 (7)0.56545 (5)0.01764 (17)
O40.64137 (7)0.28582 (7)0.58760 (6)0.02162 (18)
O50.76326 (7)0.23729 (8)0.46864 (6)0.02367 (19)
O60.51248 (8)0.64805 (7)0.31004 (6)0.02113 (18)
H60.4708 (15)0.6687 (17)0.3414 (13)0.037 (5)*
C10.46538 (8)0.19325 (9)0.48278 (7)0.0134 (2)
C20.56568 (8)0.14374 (9)0.45337 (7)0.0125 (2)
H210.5641 (11)0.0631 (13)0.4642 (9)0.013 (3)*
C30.57717 (8)0.16968 (9)0.35592 (7)0.0127 (2)
H310.6466 (12)0.1471 (12)0.3433 (9)0.015 (3)*
C40.56215 (8)0.29631 (9)0.34215 (7)0.0128 (2)
C50.60639 (9)0.35682 (9)0.27266 (7)0.0138 (2)
C60.58971 (9)0.47646 (9)0.26287 (7)0.0154 (2)
C70.52702 (9)0.53432 (9)0.32264 (7)0.0155 (2)
C80.48201 (9)0.47477 (9)0.38750 (7)0.0151 (2)
H810.4406 (13)0.5087 (15)0.4253 (11)0.029 (4)*
C90.50004 (9)0.35658 (9)0.39486 (7)0.0130 (2)
C100.66465 (9)0.29916 (10)0.21058 (8)0.0185 (2)
H1010.6760 (12)0.2190 (14)0.2166 (10)0.023 (4)*
C110.70274 (10)0.35731 (11)0.14187 (8)0.0223 (3)
H1110.7417 (14)0.3187 (16)0.1015 (11)0.031 (4)*
C120.68582 (10)0.47584 (11)0.13268 (8)0.0230 (3)
H1210.7108 (13)0.5141 (15)0.0840 (11)0.030 (4)*
C130.63152 (10)0.53456 (11)0.19212 (8)0.0198 (2)
H1310.6213 (14)0.6112 (16)0.1843 (11)0.029 (4)*
C140.50280 (8)0.09639 (9)0.29837 (7)0.0132 (2)
C150.52697 (9)−0.01874 (10)0.28509 (7)0.0174 (2)
H1510.5900 (13)−0.0521 (14)0.3119 (11)0.028 (4)*
C160.46203 (10)−0.08798 (10)0.23236 (8)0.0192 (2)
H1610.4786 (13)−0.1668 (15)0.2241 (11)0.029 (4)*
C170.37239 (9)−0.04082 (10)0.19235 (8)0.0182 (2)
C180.34500 (9)0.07230 (10)0.20549 (8)0.0200 (2)
H1810.2817 (15)0.1014 (16)0.1791 (11)0.034 (5)*
C190.41108 (9)0.14036 (10)0.25875 (8)0.0177 (2)
H1910.3946 (12)0.2175 (14)0.2675 (10)0.024 (4)*
C200.80761 (10)0.07514 (11)0.62439 (8)0.0232 (2)
H2010.79040.09940.68180.028*
H2020.86380.12480.60490.028*
C210.84199 (12)−0.04818 (12)0.62500 (10)0.0307 (3)
H2110.7840−0.09670.64060.046*
H2120.9011−0.05820.66620.046*
H2130.8631−0.06950.56860.046*
C220.79348 (14)0.35651 (15)0.45674 (12)0.0447 (5)
H2210.72800.39740.44030.054*0.175 (5)
H2220.81610.38490.51370.054*0.175 (5)
H2230.77980.36830.39660.054*0.825 (5)
H2240.75220.40540.49120.054*0.825 (5)
C23A0.8601 (7)0.3928 (8)0.4080 (6)0.035 (3)0.175 (5)
H2310.92770.35680.42240.052*0.175 (5)
H2320.86680.47550.41420.052*0.175 (5)
H2330.83780.37430.34940.052*0.175 (5)
C23B0.91138 (16)0.3623 (2)0.47651 (14)0.0459 (7)0.825 (5)
H2340.94620.30510.44290.069*0.825 (5)
H2350.92660.34730.53680.069*0.825 (5)
H2360.93690.43830.46250.069*0.825 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br0.02545 (7)0.01887 (7)0.03304 (9)−0.00433 (4)−0.00962 (5)−0.00515 (5)
P0.01309 (12)0.01055 (12)0.01589 (14)0.00006 (9)−0.00051 (10)−0.00060 (10)
O10.0152 (4)0.0130 (4)0.0168 (4)0.0027 (3)0.0054 (3)0.0036 (3)
O20.0181 (4)0.0180 (4)0.0214 (4)−0.0010 (3)0.0058 (3)0.0047 (3)
O30.0168 (4)0.0131 (4)0.0222 (4)0.0020 (3)−0.0059 (3)−0.0002 (3)
O40.0215 (4)0.0166 (4)0.0263 (5)0.0036 (3)−0.0034 (3)−0.0081 (3)
O50.0178 (4)0.0275 (5)0.0259 (5)−0.0091 (3)0.0025 (3)0.0021 (4)
O60.0292 (5)0.0105 (4)0.0240 (5)0.0015 (3)0.0038 (4)0.0033 (3)
C10.0140 (5)0.0131 (5)0.0131 (5)0.0006 (4)−0.0003 (4)0.0002 (4)
C20.0125 (5)0.0103 (5)0.0147 (5)0.0002 (4)0.0001 (4)0.0003 (4)
C30.0133 (5)0.0111 (5)0.0139 (5)0.0009 (4)0.0022 (4)−0.0003 (4)
C40.0134 (5)0.0109 (5)0.0142 (5)−0.0003 (4)0.0011 (4)0.0004 (4)
C50.0132 (5)0.0145 (5)0.0138 (5)−0.0024 (4)0.0018 (4)−0.0003 (4)
C60.0165 (5)0.0149 (5)0.0149 (5)−0.0033 (4)0.0007 (4)0.0010 (4)
C70.0184 (5)0.0110 (5)0.0168 (5)−0.0008 (4)−0.0014 (4)0.0009 (4)
C80.0179 (5)0.0128 (5)0.0148 (5)0.0027 (4)0.0018 (4)−0.0010 (4)
C90.0143 (5)0.0125 (5)0.0124 (5)−0.0006 (4)0.0014 (4)0.0020 (4)
C100.0177 (5)0.0185 (5)0.0200 (6)−0.0014 (4)0.0061 (4)−0.0021 (4)
C110.0206 (6)0.0277 (6)0.0195 (6)−0.0056 (5)0.0078 (5)−0.0031 (5)
C120.0238 (6)0.0273 (6)0.0185 (6)−0.0106 (5)0.0053 (5)0.0029 (5)
C130.0223 (6)0.0181 (6)0.0191 (6)−0.0061 (4)0.0012 (4)0.0043 (4)
C140.0154 (5)0.0119 (5)0.0123 (5)−0.0004 (4)0.0014 (4)0.0000 (4)
C150.0196 (5)0.0134 (5)0.0188 (5)0.0030 (4)−0.0029 (4)−0.0007 (4)
C160.0240 (6)0.0118 (5)0.0216 (6)0.0011 (4)−0.0014 (5)−0.0008 (4)
C170.0197 (5)0.0152 (5)0.0193 (6)−0.0042 (4)−0.0026 (4)−0.0014 (4)
C180.0173 (5)0.0180 (5)0.0241 (6)0.0018 (4)−0.0044 (5)−0.0003 (4)
C190.0181 (5)0.0129 (5)0.0218 (6)0.0025 (4)−0.0014 (4)−0.0012 (4)
C200.0201 (5)0.0240 (6)0.0243 (6)0.0013 (5)−0.0098 (5)−0.0001 (5)
C210.0297 (7)0.0297 (7)0.0316 (7)0.0116 (6)−0.0093 (6)0.0027 (6)
C220.0430 (9)0.0416 (9)0.0475 (10)−0.0302 (7)−0.0147 (8)0.0203 (7)
C23A0.028 (4)0.042 (5)0.035 (5)−0.020 (4)0.011 (3)0.001 (4)
C23B0.0330 (10)0.0670 (16)0.0380 (12)−0.0320 (10)0.0053 (8)−0.0058 (10)
Geometric parameters (Å, º) top
Br—C171.9255 (12)C12—H1210.963 (17)
P—O41.4964 (9)C13—H1310.918 (18)
P—O31.5762 (8)C14—C191.4015 (16)
P—O51.5790 (9)C14—C151.4064 (15)
P—C21.8560 (11)C15—C161.4062 (17)
O1—C11.3708 (13)C15—H1510.976 (17)
O1—C91.4199 (13)C16—C171.3969 (17)
O2—C11.2085 (14)C16—H1610.961 (18)
O3—C201.4810 (14)C17—C181.3935 (16)
O5—C221.4684 (17)C18—C191.4112 (17)
O6—C71.3625 (13)C18—H1810.956 (19)
O6—H60.79 (2)C19—H1910.943 (16)
C1—C21.5096 (15)C20—C211.5146 (19)
C2—C31.5889 (15)C20—H2010.9900
C2—H210.963 (15)C20—H2020.9900
C3—C41.5146 (14)C21—H2110.9800
C3—C141.5452 (15)C21—H2120.9800
C3—H310.961 (15)C21—H2130.9800
C4—C91.3815 (15)C22—C23A1.259 (8)
C4—C51.4526 (15)C22—C23B1.530 (3)
C5—C61.4290 (15)C22—H2210.9900
C5—C101.4379 (15)C22—H2220.9900
C6—C131.4414 (15)C22—H2230.9700
C6—C71.4462 (15)C22—H2240.9699
C7—C81.3948 (15)C23A—H2231.0758
C8—C91.4117 (15)C23A—H2310.9800
C8—H810.914 (17)C23A—H2320.9800
C10—C111.3967 (17)C23A—H2330.9800
C10—H1010.957 (16)C23B—H2340.9800
C11—C121.4158 (19)C23B—H2350.9800
C11—H1110.949 (18)C23B—H2360.9800
C12—C131.3863 (18)
O4—P—O3115.66 (5)C14—C15—H151120.4 (10)
O4—P—O5113.99 (5)C17—C16—C15119.09 (10)
O3—P—O5104.07 (5)C17—C16—H161120.3 (10)
O4—P—C2114.94 (5)C15—C16—H161120.7 (10)
O3—P—C299.90 (5)C18—C17—C16121.24 (11)
O5—P—C2106.75 (5)C18—C17—Br119.10 (9)
C1—O1—C9120.84 (8)C16—C17—Br119.66 (9)
C20—O3—P122.65 (8)C17—C18—C19118.80 (11)
C22—O5—P124.17 (11)C17—C18—H181119.4 (11)
C7—O6—H6107.5 (15)C19—C18—H181121.8 (11)
O2—C1—O1119.06 (10)C14—C19—C18121.39 (10)
O2—C1—C2124.74 (10)C14—C19—H191118.5 (10)
O1—C1—C2116.19 (9)C18—C19—H191120.1 (10)
C1—C2—C3110.67 (9)O3—C20—C21106.36 (10)
C1—C2—P107.08 (7)O3—C20—H201110.5
C3—C2—P115.46 (7)C21—C20—H201110.5
C1—C2—H21107.3 (8)O3—C20—H202110.5
C3—C2—H21111.4 (8)C21—C20—H202110.5
P—C2—H21104.4 (9)H201—C20—H202108.6
C4—C3—C14113.13 (9)C20—C21—H211109.5
C4—C3—C2108.09 (9)C20—C21—H212109.5
C14—C3—C2112.29 (9)H211—C21—H212109.5
C4—C3—H31110.7 (8)C20—C21—H213109.5
C14—C3—H31105.8 (9)H211—C21—H213109.5
C2—C3—H31106.7 (9)H212—C21—H213109.5
C9—C4—C5118.06 (10)C23A—C22—O5126.5 (5)
C9—C4—C3119.30 (9)C23A—C22—C23B54.0 (5)
C5—C4—C3122.56 (9)O5—C22—C23B106.36 (16)
C6—C5—C10118.01 (10)C23A—C22—H221105.7
C6—C5—C4120.09 (10)O5—C22—H221105.7
C10—C5—C4121.87 (10)C23B—C22—H221147.9
C5—C6—C13119.37 (10)C23A—C22—H222105.7
C5—C6—C7118.47 (10)O5—C22—H222105.7
C13—C6—C7122.10 (10)C23B—C22—H22264.0
O6—C7—C8122.75 (10)H221—C22—H222106.1
O6—C7—C6116.21 (10)C23A—C22—H22355.9
C8—C7—C6121.00 (10)O5—C22—H223103.2
C7—C8—C9118.79 (10)C23B—C22—H223108.5
C7—C8—H81122.9 (11)H221—C22—H22364.4
C9—C8—H81118.3 (11)H222—C22—H223151.1
C4—C9—C8123.49 (10)C23A—C22—H224123.8
C4—C9—O1122.29 (9)O5—C22—H224109.6
C8—C9—O1114.09 (9)C23B—C22—H224115.1
C11—C10—C5121.38 (11)H221—C22—H22451.6
C11—C10—H101120.1 (9)H222—C22—H22455.2
C5—C10—H101118.5 (9)H223—C22—H224113.2
C10—C11—C12120.21 (11)C22—C23A—H22348.3
C10—C11—H111120.8 (11)C22—C23A—H231109.5
C12—C11—H111118.9 (11)H223—C23A—H231138.7
C13—C12—C11119.98 (11)C22—C23A—H232109.5
C13—C12—H121120.9 (10)H223—C23A—H232111.1
C11—C12—H121119.1 (10)C22—C23A—H233109.5
C12—C13—C6121.04 (11)H223—C23A—H23363.6
C12—C13—H131118.1 (11)C22—C23B—H234109.5
C6—C13—H131120.9 (11)C22—C23B—H235109.5
C19—C14—C15118.31 (10)H234—C23B—H235109.5
C19—C14—C3122.33 (10)C22—C23B—H236109.5
C15—C14—C3119.36 (10)H234—C23B—H236109.5
C16—C15—C14121.13 (11)H235—C23B—H236109.5
C16—C15—H151118.5 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6···O4i0.79 (2)1.95 (2)2.737 (1)175 (2)
Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC23H22BrO6P
Mr505.29
Crystal system, space groupMonoclinic, P21/n
Temperature (K)90
a, b, c (Å)12.8328 (5), 11.7500 (5), 15.8477 (7)
β (°) 93.184 (1)
V (Å3)2385.91 (17)
Z4
Radiation typeMo Kα
µ (mm−1)1.83
Crystal size (mm)0.20 × 0.20 × 0.10
Data collection
DiffractometerBruker SMART APEX
Absorption correctionMulti-scan
(SHELXTL; Bruker, 2003)
Tmin, Tmax0.697, 0.839
No. of measured, independent and
observed [I > 2σ(I)] reflections		54317, 6239, 5698
Rint0.021
(sin θ/λ)max (Å−1)0.682
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.023, 0.064, 1.04
No. of reflections6239
No. of parameters341
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.43, −0.38

Computer programs: SMART (Bruker, 2003), SAINT-Plus (Bruker, 2003), SHELXTL (Bruker, 2003).

Selected geometric parameters (Å, º) top
Br—C171.9255 (12)P—C21.8560 (11)
P—O41.4964 (9)O1—C11.3708 (13)
P—O31.5762 (8)O1—C91.4199 (13)
P—O51.5790 (9)O2—C11.2085 (14)
O4—P—O3115.66 (5)O4—P—C2114.94 (5)
O4—P—O5113.99 (5)O3—P—C299.90 (5)
O3—P—O5104.07 (5)O5—P—C2106.75 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6···O4i0.79 (2)1.95 (2)2.737 (1)175 (2)
Symmetry code: (i) −x+1, −y+1, −z+1.
 

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