organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Tris(2,4-di-tert-butyl­phen­yl) phosphate

aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: d_velu@yahoo.com

(Received 18 June 2010; accepted 26 July 2010; online 4 August 2010)

The title compound, C42H63O4P, was isolated from the leaves of Vitex negundo. Two of the tert-butyl groups are disordered over two orientations with occupancy ratios of 0.57 (1):0.43 (1) and 0.67 (1):0.33 (1). Several intra­molecular C—H⋯O inter­actions are observed in the mol­ecular structure.

Related literature

For general background and the biological activity of Vitex negundo, see: Aswar et al. (2009[Aswar, P. B., Khadabadi, S. S., Kuchekar, B. S., Rajurkar, R. M., Saboo, S. S. & Javarkar, R. D. (2009). Ethnobotanical Leaflets, 13, 962-967.]); Chadha (1976[Chadha, Y. R. (1976). The Wealth of India: A Dictionary of Indian Raw Materials and Industrial Products, Vol. 10, pp. 522-524. New Delhi: Publication Information Directorate, CSIR.]); Kulkarni et al. (2008[Kulkarni, R. R., Virkar, A. D. & D'Mello, P. (2008). Indian J. Pharm. Sci. 70, 838-840.]); Sahare et al. (2008[Sahare, K. N., Anandharaman, V., Meshram, V. G., Meshram, S. U., Gajalakshmi, D., Goswami, K. & Reddy, M. V. R. (2008). Indian J. Med. Res. 127, 469-471.]); Rastogi et al. (2009[Rastogi, T., Bhutda, V., Moon, K., Aswar, P. B. & Khadabadi, S. S. (2009). Asian J. Res. Chem. 2, 181-182.]). For the geometry of the 2,4-di-tert-butyl­phenyl group, see: Janse van Rensburg et al. (2006[Janse van Rensburg, J. M., Roodt, A. & Muller, A. (2006). Acta Cryst. E62, m2978-m2980.]).

[Scheme 1]

Experimental

Crystal data
  • C42H63O4P

  • Mr = 662.89

  • Monoclinic, P 21 /n

  • a = 15.702 (4) Å

  • b = 16.262 (4) Å

  • c = 16.262 (4) Å

  • β = 91.578 (6)°

  • V = 4150.9 (18) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 293 K

  • 0.25 × 0.22 × 0.19 mm

Data collection
  • Bruker Kappa APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008a[Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.]) Tmin = 0.975, Tmax = 0.981

  • 40376 measured reflections

  • 10329 independent reflections

  • 5669 reflections with I > 2σ(I)

  • Rint = 0.048

Refinement
  • R[F2 > 2σ(F2)] = 0.057

  • wR(F2) = 0.184

  • S = 1.02

  • 10329 reflections

  • 480 parameters

  • 96 restraints

  • H-atom parameters constrained

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.34 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C3—H3⋯O2 0.93 2.32 3.017 (3) 132
C12—H12C⋯O1 0.96 2.36 3.022 (4) 125
C13—H13A⋯O1 0.96 2.37 2.996 (3) 122
C16—H16⋯O2 0.93 2.38 3.023 (3) 126
C27—H27B⋯O3 0.96 2.40 3.032 (3) 123
C28—H28B⋯O3 0.96 2.33 2.990 (4) 125
C30—H30⋯O2 0.93 2.32 3.019 (3) 132
C36—H36A⋯O4 0.96 2.31 2.969 (3) 125
C37—H37C⋯O4 0.96 2.40 3.044 (3) 124

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Vitex negundo is one of the most common Indian medicinal plants which is used in Indian Folk medicine in the treatment of various ailments (Aswar et al., 2009). Though, almost all parts of V. negundo are used, the leaves and the barks are the most important in the field of medicine (Chadha, 1976). The roots of V. negundo was reported to have antifilarial activity (Sahare et al., 2008) and antihelmintic activity (Rastogi et al., 2009). The methanol extract of V. negundo leaves standardized in terms of total polyphenol content was reported to have good free radical scavenging activity and anti-inflammatory activity (Kulkarni et al., 2008). Many phenolic and polyphenolic compounds (secondary metabolites) were isolated from various plant sources so far, but the title compound is a new class of phenolic compound that has been isolated from the leaves of V. negundo, leading to an idea of new biosynthetic pathway of phenolics in plants and screening of their various biological activities for therapeutical approaches. It is a high molecular weight substituted phenolic compound. It is a class of primary anti-oxidant (free radical scavengers) which combines with peroxide radicals and breaks autocatalytic cycle. We report here its crystal structure.

In the title molecule (Fig. 1), the O—P—O angles around the P atom deviate significantly from ideal tetrahedral values. The dihedral angles between the benzene rings C1–C6 (A), C15–C20 (B) and C29–C34 (C) are: A/B = 73.0 (1)°, A/C = 67.0 (1)° and B/C = 76.9 (1)°. The O atoms are coplanar with the attached benzene rings which is evident from the torsion angles 175.6 (2)° (O1—C4—C5—C6), -174.4 (2)° (O3—C15—C16—C17) and -176.6 (2)° (O4—C29—C30—C31). In the molecular structure, several C—H···O interactions are observed (Table 1).

Related literature top

For general background and the biological activity of Vitex negundo, see: Aswar et al. (2009); Chadha (1976); Kulkarni et al. (2008); Sahare et al. (2008); Rastogi et al. (2009). For the geometry of the 2,4-di-tert-butylphenyl group, see: Janse van Rensburg et al. (2006)

Experimental top

Vitex negundo leaves were collected in Kolli Hills, Namakkal, during April, 2008 and were identified by a botanical expert. Tris-(2,4-di-tert-butylphenyl)phosphate was isolated from the ethyl acetate extract of the leaves of V. negundo by silica gel column chromatography with gradient mixtures of hexane and ethyl acetate. White crystals were obtained by slow evaporation of an ethyl acetate solution. (m.p. 454 K-459 K).

Refinement top

The C7 and C21 tert-butyl groups are disordered over two orientations, with occupancies of 0.567 (14) and 0.433 (14), and 0.668 (7) and 0.332 (7), respectively. The corresponding bond distances involving the disorderded atoms were restrained to be equal. The Uij components of the disordered atoms were approximated to isotropic behaviour. H atoms were positioned geometrically and allowed to ride on their parent C atoms, with C–H distances in the range 0.93–0.97 Å and with Uiso(H) = 1.5Ueq(C) for methyl H and 1.2Ueq(C) for other H atoms.

Structure description top

Vitex negundo is one of the most common Indian medicinal plants which is used in Indian Folk medicine in the treatment of various ailments (Aswar et al., 2009). Though, almost all parts of V. negundo are used, the leaves and the barks are the most important in the field of medicine (Chadha, 1976). The roots of V. negundo was reported to have antifilarial activity (Sahare et al., 2008) and antihelmintic activity (Rastogi et al., 2009). The methanol extract of V. negundo leaves standardized in terms of total polyphenol content was reported to have good free radical scavenging activity and anti-inflammatory activity (Kulkarni et al., 2008). Many phenolic and polyphenolic compounds (secondary metabolites) were isolated from various plant sources so far, but the title compound is a new class of phenolic compound that has been isolated from the leaves of V. negundo, leading to an idea of new biosynthetic pathway of phenolics in plants and screening of their various biological activities for therapeutical approaches. It is a high molecular weight substituted phenolic compound. It is a class of primary anti-oxidant (free radical scavengers) which combines with peroxide radicals and breaks autocatalytic cycle. We report here its crystal structure.

In the title molecule (Fig. 1), the O—P—O angles around the P atom deviate significantly from ideal tetrahedral values. The dihedral angles between the benzene rings C1–C6 (A), C15–C20 (B) and C29–C34 (C) are: A/B = 73.0 (1)°, A/C = 67.0 (1)° and B/C = 76.9 (1)°. The O atoms are coplanar with the attached benzene rings which is evident from the torsion angles 175.6 (2)° (O1—C4—C5—C6), -174.4 (2)° (O3—C15—C16—C17) and -176.6 (2)° (O4—C29—C30—C31). In the molecular structure, several C—H···O interactions are observed (Table 1).

For general background and the biological activity of Vitex negundo, see: Aswar et al. (2009); Chadha (1976); Kulkarni et al. (2008); Sahare et al. (2008); Rastogi et al. (2009). For the geometry of the 2,4-di-tert-butylphenyl group, see: Janse van Rensburg et al. (2006)

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008b) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids drawn at the 30% probability level. Both disordercomponents are shown. H atoms have been omitted for clarity.
Tris(2,4-di-tert-butylphenyl) phosphate top
Crystal data top
C42H63O4PF(000) = 1448
Mr = 662.89Dx = 1.061 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3749 reflections
a = 15.702 (4) Åθ = 1.8–28.6°
b = 16.262 (4) ŵ = 0.10 mm1
c = 16.262 (4) ÅT = 293 K
β = 91.578 (6)°Block, white
V = 4150.9 (18) Å30.25 × 0.22 × 0.19 mm
Z = 4
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer
10329 independent reflections
Radiation source: fine-focus sealed tube5669 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
ω and φ scansθmax = 28.6°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008a)
h = 2020
Tmin = 0.975, Tmax = 0.981k = 2121
40376 measured reflectionsl = 1921
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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0826P)2 + 0.8971P]
where P = (Fo2 + 2Fc2)/3
10329 reflections(Δ/σ)max = 0.001
480 parametersΔρmax = 0.37 e Å3
96 restraintsΔρmin = 0.34 e Å3
Crystal data top
C42H63O4PV = 4150.9 (18) Å3
Mr = 662.89Z = 4
Monoclinic, P21/nMo Kα radiation
a = 15.702 (4) ŵ = 0.10 mm1
b = 16.262 (4) ÅT = 293 K
c = 16.262 (4) Å0.25 × 0.22 × 0.19 mm
β = 91.578 (6)°
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer
10329 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008a)
5669 reflections with I > 2σ(I)
Tmin = 0.975, Tmax = 0.981Rint = 0.048
40376 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05796 restraints
wR(F2) = 0.184H-atom parameters constrained
S = 1.02Δρmax = 0.37 e Å3
10329 reflectionsΔρmin = 0.34 e Å3
480 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)
P10.80834 (3)0.31741 (3)0.17910 (4)0.04635 (17)
O10.77840 (9)0.32898 (10)0.08683 (10)0.0541 (4)
O20.75319 (10)0.26971 (9)0.23155 (10)0.0544 (4)
O30.90074 (9)0.28306 (9)0.16739 (11)0.0561 (4)
O40.82627 (10)0.40839 (9)0.20586 (10)0.0548 (4)
C10.53071 (13)0.35143 (13)0.01505 (15)0.0488 (5)
C20.54388 (14)0.32741 (14)0.06516 (15)0.0533 (6)
H20.49720.31470.09680.064*
C30.62501 (14)0.32170 (14)0.10006 (15)0.0522 (6)
H30.63250.30570.15470.063*
C40.69482 (13)0.33985 (13)0.05346 (14)0.0450 (5)
C50.68692 (14)0.36596 (13)0.02816 (14)0.0493 (5)
C60.60322 (14)0.36998 (14)0.05986 (15)0.0543 (6)
H60.59520.38610.11440.065*
C70.44112 (15)0.35747 (16)0.05561 (16)0.0607 (6)
C80.4393 (6)0.3024 (6)0.1327 (6)0.085 (3)0.567 (14)
H8A0.44020.24570.11630.102*0.567 (14)
H8B0.48820.31390.16490.102*0.567 (14)
H8C0.38830.31320.16480.102*0.567 (14)
C90.3724 (4)0.3209 (9)0.0000 (5)0.107 (3)0.567 (14)
H9A0.39500.27330.02790.129*0.567 (14)
H9B0.32350.30540.03320.129*0.567 (14)
H9C0.35620.36120.03970.129*0.567 (14)
C100.4207 (7)0.4443 (5)0.0816 (8)0.103 (3)0.567 (14)
H10A0.39320.47230.03760.124*0.567 (14)
H10B0.38350.44340.12940.124*0.567 (14)
H10C0.47240.47250.09420.124*0.567 (14)
C8A0.4184 (10)0.2826 (7)0.1025 (11)0.108 (5)0.433 (14)
H8AA0.41990.23600.06630.130*0.433 (14)
H8AB0.45830.27460.14540.130*0.433 (14)
H8AC0.36210.28850.12630.130*0.433 (14)
C9A0.3777 (6)0.3814 (12)0.0089 (6)0.108 (4)0.433 (14)
H9AA0.37430.33830.04910.129*0.433 (14)
H9AB0.32270.38970.01690.129*0.433 (14)
H9AC0.39610.43130.03550.129*0.433 (14)
C10A0.4376 (8)0.4308 (8)0.1153 (8)0.089 (4)0.433 (14)
H10D0.43830.48120.08460.107*0.433 (14)
H10E0.38630.42790.14870.107*0.433 (14)
H10F0.48610.42910.15000.107*0.433 (14)
C110.76410 (15)0.38937 (16)0.08056 (16)0.0599 (6)
C120.8214 (2)0.31473 (19)0.0926 (2)0.0890 (10)
H12A0.87090.33100.12190.107*
H12B0.79070.27350.12360.107*
H12C0.83850.29270.03990.107*
C130.81492 (18)0.45868 (17)0.0382 (2)0.0806 (9)
H13A0.83940.43900.01280.097*
H13B0.77770.50410.02770.097*
H13C0.85950.47640.07330.097*
C140.7358 (2)0.4221 (3)0.1651 (2)0.1123 (13)
H14A0.78480.43950.19450.135*
H14B0.69810.46800.15840.135*
H14C0.70670.37940.19540.135*
C150.92470 (13)0.19949 (12)0.15720 (14)0.0466 (5)
C160.86524 (15)0.13759 (14)0.16109 (16)0.0573 (6)
H160.80790.15060.16570.069*
C170.89021 (16)0.05613 (14)0.15820 (16)0.0589 (6)
H170.84920.01490.16010.071*
C180.97496 (15)0.03491 (13)0.15252 (14)0.0525 (6)
C191.03290 (15)0.09966 (13)0.14503 (14)0.0524 (6)
H191.09000.08630.13920.063*
C201.01107 (14)0.18317 (13)0.14575 (14)0.0479 (5)
C211.00460 (17)0.05547 (14)0.15407 (17)0.0639 (7)
C221.0388 (5)0.0797 (3)0.0717 (3)0.098 (2)0.668 (7)
H22A1.09610.06010.06750.118*0.668 (7)
H22B1.00380.05600.02860.118*0.668 (7)
H22C1.03810.13860.06670.118*0.668 (7)
C231.0779 (5)0.0663 (3)0.2184 (4)0.117 (3)0.668 (7)
H23A1.09900.01330.23490.140*0.668 (7)
H23B1.12300.09750.19470.140*0.668 (7)
H23C1.05720.09490.26550.140*0.668 (7)
C240.9340 (4)0.1140 (3)0.1769 (6)0.130 (3)0.668 (7)
H24A0.91420.10030.23050.156*0.668 (7)
H24B0.95530.16940.17740.156*0.668 (7)
H24C0.88770.10960.13730.156*0.668 (7)
C22A0.9980 (12)0.0870 (8)0.2385 (7)0.115 (5)0.332 (7)
H22D1.03720.05790.27430.138*0.332 (7)
H22E1.01150.14460.23940.138*0.332 (7)
H22F0.94100.07900.25690.138*0.332 (7)
C23A0.9422 (8)0.1038 (6)0.0956 (9)0.114 (5)0.332 (7)
H23D0.90810.06560.06390.136*0.332 (7)
H23E0.90590.13790.12760.136*0.332 (7)
H23F0.97430.13750.05920.136*0.332 (7)
C24A1.0915 (9)0.0643 (8)0.1216 (12)0.128 (5)0.332 (7)
H24D1.13120.03420.15590.154*0.332 (7)
H24E1.09230.04320.06660.154*0.332 (7)
H24F1.10710.12140.12150.154*0.332 (7)
C251.07798 (15)0.25155 (14)0.13433 (17)0.0602 (7)
C261.16553 (17)0.21537 (19)0.1140 (2)0.0894 (10)
H26A1.18670.18330.15970.107*
H26B1.20460.25930.10340.107*
H26C1.15990.18100.06610.107*
C271.08814 (17)0.30289 (17)0.2130 (2)0.0766 (8)
H27A1.10440.26770.25820.092*
H27B1.03500.32920.22440.092*
H27C1.13130.34390.20580.092*
C281.0509 (2)0.30698 (17)0.0608 (2)0.0821 (9)
H28A1.09220.34990.05440.099*
H28B0.99620.33090.07080.099*
H28C1.04730.27450.01150.099*
C290.83683 (13)0.44192 (12)0.28703 (14)0.0461 (5)
C300.80912 (15)0.39926 (14)0.35457 (15)0.0566 (6)
H300.78600.34690.34820.068*
C310.81596 (16)0.43484 (14)0.43200 (16)0.0569 (6)
H310.79800.40540.47740.068*
C320.84884 (14)0.51314 (14)0.44336 (15)0.0523 (6)
C330.87591 (14)0.55355 (14)0.37267 (15)0.0524 (6)
H330.89810.60620.37910.063*
C340.87219 (13)0.52098 (12)0.29329 (14)0.0470 (5)
C350.90342 (15)0.56929 (13)0.21791 (16)0.0562 (6)
C360.97073 (17)0.51997 (16)0.17182 (19)0.0753 (8)
H36A0.94630.46900.15280.090*
H36B1.01850.50880.20830.090*
H36C0.98940.55130.12560.090*
C370.82689 (18)0.58997 (16)0.16050 (17)0.0707 (7)
H37A0.84640.61840.11290.085*
H37B0.78770.62430.18910.085*
H37C0.79870.54010.14370.085*
C380.9459 (2)0.65100 (16)0.2443 (2)0.0808 (9)
H38A0.96440.67980.19640.097*
H38B0.99410.63980.28010.097*
H38C0.90560.68420.27270.097*
C390.85283 (17)0.55513 (16)0.52831 (16)0.0635 (7)
C400.9374 (2)0.6003 (3)0.5429 (2)0.1156 (13)
H40A0.93960.62260.59760.139*
H40B0.94190.64410.50370.139*
H40C0.98370.56250.53650.139*
C410.7845 (2)0.6210 (3)0.5294 (2)0.1212 (15)
H41A0.72930.59560.52580.145*
H41B0.79100.65720.48340.145*
H41C0.78980.65190.57960.145*
C420.8437 (3)0.4962 (2)0.5980 (2)0.1315 (16)
H42A0.78730.47340.59630.158*
H42B0.85330.52460.64920.158*
H42C0.88470.45280.59330.158*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0426 (3)0.0424 (3)0.0536 (4)0.0009 (2)0.0056 (2)0.0007 (3)
O10.0401 (8)0.0708 (10)0.0512 (10)0.0022 (7)0.0023 (7)0.0024 (8)
O20.0534 (9)0.0509 (8)0.0583 (11)0.0046 (7)0.0054 (7)0.0050 (7)
O30.0408 (8)0.0416 (8)0.0853 (12)0.0017 (6)0.0073 (7)0.0025 (8)
O40.0687 (10)0.0426 (8)0.0530 (10)0.0014 (7)0.0015 (8)0.0003 (7)
C10.0449 (12)0.0515 (12)0.0497 (15)0.0002 (10)0.0052 (10)0.0044 (10)
C20.0424 (12)0.0627 (14)0.0550 (16)0.0018 (10)0.0024 (10)0.0029 (11)
C30.0459 (12)0.0635 (14)0.0470 (14)0.0016 (10)0.0003 (10)0.0058 (11)
C40.0402 (11)0.0466 (11)0.0481 (14)0.0005 (9)0.0034 (9)0.0028 (10)
C50.0484 (12)0.0510 (12)0.0484 (15)0.0038 (10)0.0012 (10)0.0005 (10)
C60.0534 (13)0.0635 (14)0.0455 (15)0.0032 (11)0.0058 (10)0.0022 (11)
C70.0475 (13)0.0712 (16)0.0624 (17)0.0014 (11)0.0130 (11)0.0046 (13)
C80.063 (4)0.103 (6)0.086 (5)0.008 (3)0.029 (3)0.020 (4)
C90.051 (3)0.177 (8)0.092 (5)0.024 (4)0.012 (3)0.016 (5)
C100.077 (5)0.067 (4)0.163 (8)0.015 (3)0.036 (5)0.014 (5)
C8A0.088 (7)0.074 (5)0.161 (10)0.010 (5)0.042 (7)0.019 (6)
C9A0.047 (4)0.167 (9)0.109 (6)0.027 (6)0.009 (4)0.002 (6)
C10A0.061 (5)0.096 (7)0.109 (7)0.016 (4)0.037 (5)0.012 (6)
C110.0535 (13)0.0757 (16)0.0509 (16)0.0086 (12)0.0065 (11)0.0057 (12)
C120.084 (2)0.091 (2)0.094 (2)0.0067 (17)0.0424 (18)0.0130 (17)
C130.0713 (18)0.0772 (18)0.094 (2)0.0210 (15)0.0206 (16)0.0024 (16)
C140.087 (2)0.185 (4)0.065 (2)0.025 (2)0.0074 (17)0.040 (2)
C150.0464 (12)0.0394 (10)0.0536 (14)0.0013 (9)0.0089 (10)0.0027 (9)
C160.0442 (12)0.0505 (13)0.0766 (18)0.0010 (10)0.0080 (11)0.0065 (12)
C170.0619 (15)0.0447 (12)0.0702 (18)0.0076 (11)0.0007 (12)0.0071 (11)
C180.0661 (15)0.0438 (11)0.0477 (15)0.0012 (10)0.0044 (11)0.0045 (10)
C190.0523 (13)0.0500 (12)0.0552 (15)0.0089 (10)0.0056 (10)0.0016 (11)
C200.0495 (12)0.0464 (11)0.0478 (14)0.0005 (10)0.0010 (10)0.0014 (10)
C210.0820 (18)0.0429 (12)0.0674 (18)0.0071 (12)0.0121 (14)0.0018 (12)
C220.154 (5)0.060 (3)0.082 (4)0.037 (3)0.010 (3)0.013 (2)
C230.159 (6)0.068 (3)0.122 (5)0.045 (3)0.043 (4)0.000 (3)
C240.126 (5)0.055 (3)0.211 (8)0.000 (3)0.045 (5)0.034 (4)
C22A0.157 (9)0.086 (6)0.103 (8)0.036 (7)0.008 (7)0.026 (6)
C23A0.142 (9)0.061 (5)0.136 (9)0.021 (6)0.021 (7)0.029 (6)
C24A0.146 (9)0.082 (6)0.160 (10)0.041 (6)0.048 (7)0.014 (7)
C250.0506 (13)0.0508 (12)0.0797 (19)0.0050 (10)0.0095 (12)0.0014 (12)
C260.0595 (17)0.0759 (18)0.134 (3)0.0055 (14)0.0286 (18)0.0014 (18)
C270.0587 (16)0.0699 (16)0.101 (2)0.0147 (13)0.0051 (15)0.0120 (16)
C280.090 (2)0.0639 (16)0.094 (2)0.0081 (15)0.0217 (17)0.0146 (15)
C290.0455 (11)0.0422 (11)0.0504 (14)0.0043 (9)0.0021 (9)0.0021 (10)
C300.0662 (15)0.0452 (12)0.0583 (17)0.0046 (11)0.0019 (12)0.0020 (11)
C310.0661 (15)0.0532 (13)0.0512 (16)0.0006 (11)0.0000 (11)0.0060 (11)
C320.0469 (12)0.0512 (12)0.0584 (16)0.0073 (10)0.0053 (10)0.0033 (11)
C330.0476 (12)0.0447 (11)0.0646 (17)0.0004 (9)0.0014 (11)0.0043 (11)
C340.0404 (11)0.0435 (11)0.0570 (15)0.0035 (9)0.0000 (9)0.0001 (10)
C350.0597 (14)0.0440 (11)0.0653 (17)0.0014 (10)0.0105 (12)0.0002 (11)
C360.0670 (16)0.0689 (16)0.091 (2)0.0023 (13)0.0262 (15)0.0037 (15)
C370.0847 (19)0.0614 (15)0.0661 (19)0.0085 (14)0.0052 (14)0.0117 (13)
C380.100 (2)0.0547 (14)0.089 (2)0.0185 (15)0.0223 (17)0.0017 (14)
C390.0652 (16)0.0664 (15)0.0586 (17)0.0062 (13)0.0038 (12)0.0064 (13)
C400.112 (3)0.143 (3)0.092 (3)0.027 (3)0.007 (2)0.048 (2)
C410.116 (3)0.148 (3)0.099 (3)0.054 (3)0.000 (2)0.044 (3)
C420.229 (5)0.100 (3)0.065 (2)0.021 (3)0.008 (3)0.002 (2)
Geometric parameters (Å, º) top
P1—O21.4559 (16)C21—C241.516 (5)
P1—O41.5655 (16)C21—C231.543 (6)
P1—O31.5712 (15)C21—C23A1.559 (10)
P1—O11.5713 (17)C22—H22A0.96
O1—C41.417 (3)C22—H22B0.96
O3—C151.421 (2)C22—H22C0.96
O4—C291.434 (3)C23—H23A0.96
C1—C21.372 (3)C23—H23B0.96
C1—C61.401 (3)C23—H23C0.96
C1—C71.540 (3)C24—H24A0.96
C2—C31.384 (3)C24—H24B0.96
C2—H20.93C24—H24C0.96
C3—C41.382 (3)C22A—H22D0.96
C3—H30.93C22A—H22E0.96
C4—C51.396 (3)C22A—H22F0.96
C5—C61.400 (3)C23A—H23D0.96
C5—C111.548 (3)C23A—H23E0.96
C6—H60.93C23A—H23F0.96
C7—C8A1.475 (9)C24A—H24D0.96
C7—C101.506 (9)C24A—H24E0.96
C7—C9A1.517 (8)C24A—H24F0.96
C7—C10A1.538 (9)C25—C271.533 (4)
C7—C81.540 (8)C25—C261.540 (3)
C7—C91.546 (7)C25—C281.548 (4)
C8—H8A0.96C26—H26A0.96
C8—H8B0.96C26—H26B0.96
C8—H8C0.96C26—H26C0.96
C9—H9A0.96C27—H27A0.96
C9—H9B0.96C27—H27B0.96
C9—H9C0.96C27—H27C0.96
C10—H10A0.96C28—H28A0.96
C10—H10B0.96C28—H28B0.96
C10—H10C0.96C28—H28C0.96
C8A—H8AA0.96C29—C301.380 (3)
C8A—H8AB0.96C29—C341.403 (3)
C8A—H8AC0.96C30—C311.387 (3)
C9A—H9AA0.96C30—H300.9300
C9A—H9AB0.96C31—C321.385 (3)
C9A—H9AC0.96C31—H310.9300
C10A—H10D0.96C32—C331.400 (3)
C10A—H10E0.96C32—C391.541 (3)
C10A—H10F0.96C33—C341.395 (3)
C11—C121.527 (4)C33—H330.9300
C11—C141.528 (4)C34—C351.547 (3)
C11—C131.533 (4)C35—C361.538 (3)
C12—H12A0.96C35—C371.538 (4)
C12—H12B0.96C35—C381.542 (3)
C12—H12C0.96C36—H36A0.96
C13—H13A0.96C36—H36B0.96
C13—H13B0.96C36—H36C0.96
C13—H13C0.96C37—H37A0.96
C14—H14A0.96C37—H37B0.96
C14—H14B0.96C37—H37C0.96
C14—H14C0.96C38—H38A0.96
C15—C161.376 (3)C38—H38B0.96
C15—C201.399 (3)C38—H38C0.96
C16—C171.383 (3)C39—C421.494 (4)
C16—H160.9300C39—C411.517 (4)
C17—C181.380 (3)C39—C401.530 (4)
C17—H170.9300C40—H40A0.96
C18—C191.399 (3)C40—H40B0.96
C18—C211.542 (3)C40—H40C0.96
C19—C201.401 (3)C41—H41A0.96
C19—H190.9300C41—H41B0.96
C20—C251.545 (3)C41—H41C0.96
C21—C22A1.472 (9)C42—H42A0.96
C21—C24A1.483 (10)C42—H42B0.96
C21—C221.509 (5)C42—H42C0.96
O2—P1—O4116.48 (9)C22—C21—C23107.2 (4)
O2—P1—O3116.59 (9)C24—C21—C23107.4 (5)
O4—P1—O3102.13 (8)C18—C21—C23109.8 (3)
O2—P1—O1117.14 (9)C22A—C21—C23A109.6 (8)
O4—P1—O1101.49 (9)C24A—C21—C23A107.6 (9)
O3—P1—O1100.36 (9)C22—C21—C23A63.8 (6)
C4—O1—P1129.05 (14)C24—C21—C23A51.8 (6)
C15—O3—P1127.04 (13)C18—C21—C23A106.6 (4)
C29—O4—P1129.11 (14)C23—C21—C23A143.2 (5)
C2—C1—C6116.9 (2)C21—C22—H22A109.5
C2—C1—C7122.5 (2)C21—C22—H22B109.5
C6—C1—C7120.6 (2)H22A—C22—H22B109.5
C1—C2—C3121.5 (2)C21—C22—H22C109.5
C1—C2—H2119.3H22A—C22—H22C109.5
C3—C2—H2119.3H22B—C22—H22C109.5
C4—C3—C2119.7 (2)C21—C23—H23A109.5
C4—C3—H3120.1C21—C23—H23B109.5
C2—C3—H3120.1H23A—C23—H23B109.5
C3—C4—C5122.4 (2)C21—C23—H23C109.5
C3—C4—O1120.2 (2)H23A—C23—H23C109.5
C5—C4—O1117.33 (18)H23B—C23—H23C109.5
C4—C5—C6114.98 (19)C21—C24—H24A109.5
C4—C5—C11123.2 (2)C21—C24—H24B109.5
C6—C5—C11121.8 (2)H24A—C24—H24B109.5
C5—C6—C1124.5 (2)C21—C24—H24C109.5
C5—C6—H6117.8H24A—C24—H24C109.5
C1—C6—H6117.8H24B—C24—H24C109.5
C8A—C7—C10125.6 (7)C21—C22A—H22D109.5
C8A—C7—C9A114.5 (7)C21—C22A—H22E109.5
C10—C7—C9A79.3 (6)H22D—C22A—H22E109.5
C8A—C7—C10A108.0 (8)C21—C22A—H22F109.5
C9A—C7—C10A103.0 (6)H22D—C22A—H22F109.5
C10—C7—C8108.6 (6)H22E—C22A—H22F109.5
C9A—C7—C8135.6 (6)C21—C23A—H23D109.5
C10A—C7—C886.4 (6)C21—C23A—H23E109.5
C8A—C7—C1112.0 (6)H23D—C23A—H23E109.5
C10—C7—C1111.4 (5)C21—C23A—H23F109.5
C9A—C7—C1109.2 (4)H23D—C23A—H23F109.5
C10A—C7—C1109.7 (5)H23E—C23A—H23F109.5
C8—C7—C1107.9 (4)C21—C24A—H24D109.5
C8A—C7—C979.7 (6)C21—C24A—H24E109.5
C10—C7—C9112.2 (5)H24D—C24A—H24E109.5
C10A—C7—C9130.9 (6)C21—C24A—H24F109.5
C8—C7—C9104.7 (5)H24D—C24A—H24F109.5
C1—C7—C9111.6 (3)H24E—C24A—H24F109.5
C7—C8—H8A109.5C27—C25—C26108.3 (2)
C7—C8—H8B109.5C27—C25—C20110.3 (2)
H8A—C8—H8B109.5C26—C25—C20111.4 (2)
C7—C8—H8C109.5C27—C25—C28110.4 (2)
H8A—C8—H8C109.5C26—C25—C28106.5 (2)
H8B—C8—H8C109.5C20—C25—C28109.8 (2)
C7—C9—H9A109.5C25—C26—H26A109.5
C7—C9—H9B109.5C25—C26—H26B109.5
H9A—C9—H9B109.5H26A—C26—H26B109.5
C7—C9—H9C109.5C25—C26—H26C109.5
H9A—C9—H9C109.5H26A—C26—H26C109.5
H9B—C9—H9C109.5H26B—C26—H26C109.5
C7—C10—H10A109.5C25—C27—H27A109.5
C7—C10—H10B109.5C25—C27—H27B109.5
H10A—C10—H10B109.5H27A—C27—H27B109.5
C7—C10—H10C109.5C25—C27—H27C109.5
H10A—C10—H10C109.5H27A—C27—H27C109.5
H10B—C10—H10C109.5H27B—C27—H27C109.5
C7—C8A—H8AA109.5C25—C28—H28A109.5
C7—C8A—H8AB109.5C25—C28—H28B109.5
H8AA—C8A—H8AB109.5H28A—C28—H28B109.5
C7—C8A—H8AC109.5C25—C28—H28C109.5
H8AA—C8A—H8AC109.5H28A—C28—H28C109.5
H8AB—C8A—H8AC109.5H28B—C28—H28C109.5
C7—C9A—H9AA109.5C30—C29—C34122.4 (2)
C7—C9A—H9AB109.5C30—C29—O4120.71 (19)
H9AA—C9A—H9AB109.5C34—C29—O4116.79 (19)
C7—C9A—H9AC109.5C29—C30—C31119.6 (2)
H9AA—C9A—H9AC109.5C29—C30—H30120.2
H9AB—C9A—H9AC109.5C31—C30—H30120.2
C7—C10A—H10D109.5C32—C31—C30121.6 (2)
C7—C10A—H10E109.5C32—C31—H31119.2
H10D—C10A—H10E109.5C30—C31—H31119.2
C7—C10A—H10F109.5C31—C32—C33116.3 (2)
H10D—C10A—H10F109.5C31—C32—C39122.2 (2)
H10E—C10A—H10F109.5C33—C32—C39121.5 (2)
C12—C11—C14108.6 (3)C34—C33—C32125.1 (2)
C12—C11—C13109.9 (2)C34—C33—H33117.4
C14—C11—C13106.4 (2)C32—C33—H33117.4
C12—C11—C5110.4 (2)C33—C34—C29114.9 (2)
C14—C11—C5111.6 (2)C33—C34—C35122.29 (19)
C13—C11—C5109.8 (2)C29—C34—C35122.8 (2)
C11—C12—H12A109.5C36—C35—C37110.7 (2)
C11—C12—H12B109.5C36—C35—C38106.7 (2)
H12A—C12—H12B109.5C37—C35—C38107.8 (2)
C11—C12—H12C109.5C36—C35—C34111.00 (19)
H12A—C12—H12C109.5C37—C35—C34109.43 (19)
H12B—C12—H12C109.5C38—C35—C34111.2 (2)
C11—C13—H13A109.5C35—C36—H36A109.5
C11—C13—H13B109.5C35—C36—H36B109.5
H13A—C13—H13B109.5H36A—C36—H36B109.5
C11—C13—H13C109.5C35—C36—H36C109.5
H13A—C13—H13C109.5H36A—C36—H36C109.5
H13B—C13—H13C109.5H36B—C36—H36C109.5
C11—C14—H14A109.5C35—C37—H37A109.5
C11—C14—H14B109.5C35—C37—H37B109.5
H14A—C14—H14B109.5H37A—C37—H37B109.5
C11—C14—H14C109.5C35—C37—H37C109.5
H14A—C14—H14C109.5H37A—C37—H37C109.5
H14B—C14—H14C109.5H37B—C37—H37C109.5
C16—C15—C20121.93 (19)C35—C38—H38A109.5
C16—C15—O3120.82 (19)C35—C38—H38B109.5
C20—C15—O3117.23 (18)H38A—C38—H38B109.5
C15—C16—C17120.4 (2)C35—C38—H38C109.5
C15—C16—H16119.8H38A—C38—H38C109.5
C17—C16—H16119.8H38B—C38—H38C109.5
C18—C17—C16121.1 (2)C42—C39—C41111.2 (3)
C18—C17—H17119.4C42—C39—C40106.9 (3)
C16—C17—H17119.4C41—C39—C40105.7 (3)
C17—C18—C19116.6 (2)C42—C39—C32113.2 (2)
C17—C18—C21121.9 (2)C41—C39—C32108.2 (2)
C19—C18—C21121.5 (2)C40—C39—C32111.4 (2)
C18—C19—C20124.7 (2)C39—C40—H40A109.5
C18—C19—H19117.7C39—C40—H40B109.5
C20—C19—H19117.7H40A—C40—H40B109.5
C15—C20—C19115.04 (19)C39—C40—H40C109.5
C15—C20—C25122.98 (19)H40A—C40—H40C109.5
C19—C20—C25121.98 (19)H40B—C40—H40C109.5
C22A—C21—C24A112.8 (9)C39—C41—H41A109.5
C22A—C21—C22140.6 (5)C39—C41—H41B109.5
C24A—C21—C2246.0 (7)H41A—C41—H41B109.5
C22A—C21—C2458.8 (7)C39—C41—H41C109.5
C24A—C21—C24135.4 (6)H41A—C41—H41C109.5
C22—C21—C24109.5 (4)H41B—C41—H41C109.5
C22A—C21—C18108.6 (5)C39—C42—H42A109.5
C24A—C21—C18111.5 (5)C39—C42—H42B109.5
C22—C21—C18110.5 (3)H42A—C42—H42B109.5
C24—C21—C18112.4 (3)C39—C42—H42C109.5
C22A—C21—C2353.0 (6)H42A—C42—H42C109.5
C24A—C21—C2363.5 (8)H42B—C42—H42C109.5
O2—P1—O1—C436.4 (2)C16—C15—C20—C194.7 (3)
O4—P1—O1—C491.55 (18)O3—C15—C20—C19173.3 (2)
O3—P1—O1—C4163.67 (17)C16—C15—C20—C25175.0 (2)
O2—P1—O3—C1539.9 (2)O3—C15—C20—C256.9 (3)
O4—P1—O3—C15168.08 (18)C18—C19—C20—C151.8 (4)
O1—P1—O3—C1587.66 (19)C18—C19—C20—C25178.0 (2)
O2—P1—O4—C2935.9 (2)C17—C18—C21—C22A72.9 (8)
O3—P1—O4—C2992.31 (18)C19—C18—C21—C22A107.2 (8)
O1—P1—O4—C29164.32 (17)C17—C18—C21—C24A162.2 (9)
C6—C1—C2—C30.1 (3)C19—C18—C21—C24A17.6 (9)
C7—C1—C2—C3179.4 (2)C17—C18—C21—C22112.7 (4)
C1—C2—C3—C40.5 (3)C19—C18—C21—C2267.1 (4)
C2—C3—C4—C51.5 (3)C17—C18—C21—C249.9 (6)
C2—C3—C4—O1175.8 (2)C19—C18—C21—C24170.3 (5)
P1—O1—C4—C315.8 (3)C17—C18—C21—C23129.3 (4)
P1—O1—C4—C5166.79 (16)C19—C18—C21—C2350.9 (5)
C3—C4—C5—C61.8 (3)C17—C18—C21—C23A45.0 (7)
O1—C4—C5—C6175.57 (18)C19—C18—C21—C23A134.8 (7)
C3—C4—C5—C11177.9 (2)C15—C20—C25—C2765.6 (3)
O1—C4—C5—C114.7 (3)C19—C20—C25—C27114.6 (3)
C4—C5—C6—C11.2 (3)C15—C20—C25—C26174.0 (2)
C11—C5—C6—C1178.5 (2)C19—C20—C25—C265.8 (4)
C2—C1—C6—C50.3 (3)C15—C20—C25—C2856.2 (3)
C7—C1—C6—C5179.8 (2)C19—C20—C25—C28123.5 (2)
C2—C1—C7—C8A96.1 (8)P1—O4—C29—C3018.0 (3)
C6—C1—C7—C8A83.3 (8)P1—O4—C29—C34165.17 (15)
C2—C1—C7—C10117.5 (6)C34—C29—C30—C310.0 (3)
C6—C1—C7—C1063.0 (6)O4—C29—C30—C31176.6 (2)
C2—C1—C7—C9A31.8 (8)C29—C30—C31—C321.0 (4)
C6—C1—C7—C9A148.8 (8)C30—C31—C32—C331.0 (3)
C2—C1—C7—C10A144.0 (7)C30—C31—C32—C39177.0 (2)
C6—C1—C7—C10A36.6 (7)C31—C32—C33—C340.1 (3)
C2—C1—C7—C8123.4 (5)C39—C32—C33—C34178.1 (2)
C6—C1—C7—C856.1 (5)C32—C33—C34—C291.0 (3)
C2—C1—C7—C98.8 (7)C32—C33—C34—C35180.0 (2)
C6—C1—C7—C9170.6 (6)C30—C29—C34—C331.0 (3)
C4—C5—C11—C1263.7 (3)O4—C29—C34—C33175.77 (18)
C6—C5—C11—C12116.6 (3)C30—C29—C34—C35180.0 (2)
C4—C5—C11—C14175.4 (3)O4—C29—C34—C353.2 (3)
C6—C5—C11—C144.3 (4)C33—C34—C35—C36124.4 (2)
C4—C5—C11—C1357.7 (3)C29—C34—C35—C3656.7 (3)
C6—C5—C11—C13122.0 (3)C33—C34—C35—C37113.1 (2)
P1—O3—C15—C163.4 (3)C29—C34—C35—C3765.8 (3)
P1—O3—C15—C20178.51 (16)C33—C34—C35—C385.8 (3)
C20—C15—C16—C173.6 (4)C29—C34—C35—C38175.3 (2)
O3—C15—C16—C17174.4 (2)C31—C32—C39—C4217.5 (4)
C15—C16—C17—C180.9 (4)C33—C32—C39—C42164.6 (3)
C16—C17—C18—C193.6 (4)C31—C32—C39—C41106.1 (3)
C16—C17—C18—C21176.5 (2)C33—C32—C39—C4171.7 (3)
C17—C18—C19—C202.3 (4)C31—C32—C39—C40138.1 (3)
C21—C18—C19—C20177.9 (2)C33—C32—C39—C4044.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O20.932.323.017 (3)132
C12—H12C···O10.962.363.022 (4)125
C13—H13A···O10.962.372.996 (3)122
C16—H16···O20.932.383.023 (3)126
C27—H27B···O30.962.403.032 (3)123
C28—H28B···O30.962.332.990 (4)125
C30—H30···O20.932.323.019 (3)132
C36—H36A···O40.962.312.969 (3)125
C37—H37C···O40.962.403.044 (3)124

Experimental details

Crystal data
Chemical formulaC42H63O4P
Mr662.89
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)15.702 (4), 16.262 (4), 16.262 (4)
β (°) 91.578 (6)
V3)4150.9 (18)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.25 × 0.22 × 0.19
Data collection
DiffractometerBruker Kappa APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2008a)
Tmin, Tmax0.975, 0.981
No. of measured, independent and
observed [I > 2σ(I)] reflections
40376, 10329, 5669
Rint0.048
(sin θ/λ)max1)0.673
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.184, 1.02
No. of reflections10329
No. of parameters480
No. of restraints96
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.34

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008b), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008b) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O20.932.323.017 (3)132
C12—H12C···O10.962.363.022 (4)125
C13—H13A···O10.962.372.996 (3)122
C16—H16···O20.932.383.023 (3)126
C27—H27B···O30.962.403.032 (3)123
C28—H28B···O30.962.332.990 (4)125
C30—H30···O20.932.323.019 (3)132
C36—H36A···O40.962.312.969 (3)125
C37—H37C···O40.962.403.044 (3)124
 

Acknowledgements

Diffraction data were collected at the G. N. Ramachandran X-ray data-collection facility in the Department. This work was funded by the Indian Council of Medical Research (ICMR), New Delhi.

References

First citationAswar, P. B., Khadabadi, S. S., Kuchekar, B. S., Rajurkar, R. M., Saboo, S. S. & Javarkar, R. D. (2009). Ethnobotanical Leaflets, 13, 962–967.  Google Scholar
First citationBruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChadha, Y. R. (1976). The Wealth of India: A Dictionary of Indian Raw Materials and Industrial Products, Vol. 10, pp. 522–524. New Delhi: Publication Information Directorate, CSIR.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationJanse van Rensburg, J. M., Roodt, A. & Muller, A. (2006). Acta Cryst. E62, m2978–m2980.  CSD CrossRef IUCr Journals Google Scholar
First citationKulkarni, R. R., Virkar, A. D. & D'Mello, P. (2008). Indian J. Pharm. Sci. 70, 838–840.  CAS PubMed Google Scholar
First citationRastogi, T., Bhutda, V., Moon, K., Aswar, P. B. & Khadabadi, S. S. (2009). Asian J. Res. Chem. 2, 181–182.  Google Scholar
First citationSahare, K. N., Anandharaman, V., Meshram, V. G., Meshram, S. U., Gajalakshmi, D., Goswami, K. & Reddy, M. V. R. (2008). Indian J. Med. Res. 127, 469–471.  Google Scholar
First citationSheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008b). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals 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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds