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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2010 Aug 4;66(Pt 9):o2207–o2208. doi: 10.1107/S1600536810029673

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

T Vinuchakkaravarthy a, C K Sangeetha a, D Velmurugan a,*
PMCID: PMC3008051  PMID: 21588579

Abstract

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 ▶); 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 ▶).graphic file with name e-66-o2207-scheme1.jpg

Experimental

Crystal data

  • C42H63O4P

  • M r = 662.89

  • Monoclinic, Inline graphic

  • 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 ▶) T min = 0.975, T max = 0.981

  • 40376 measured reflections

  • 10329 independent reflections

  • 5669 reflections with I > 2σ(I)

  • R int = 0.048

Refinement

  • R[F 2 > 2σ(F 2)] = 0.057

  • wR(F 2) = 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

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810029673/ci5107sup1.cif

e-66-o2207-sup1.cif (37.6KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029673/ci5107Isup2.hkl

e-66-o2207-Isup2.hkl (495KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A 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
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Acknowledgments

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.

supplementary crystallographic information

Comment

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).

Experimental

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

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.

Figures

Fig. 1.

Fig. 1.

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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.

Crystal data

C42H63O4P F(000) = 1448
Mr = 662.89 Dx = 1.061 Mg m−3
Monoclinic, P21/n Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn Cell parameters from 3749 reflections
a = 15.702 (4) Å θ = 1.8–28.6°
b = 16.262 (4) Å µ = 0.10 mm−1
c = 16.262 (4) Å T = 293 K
β = 91.578 (6)° Block, white
V = 4150.9 (18) Å3 0.25 × 0.22 × 0.19 mm
Z = 4
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Data collection

Bruker Kappa APEXII CCD area-detector diffractometer 10329 independent reflections
Radiation source: fine-focus sealed tube 5669 reflections with I > 2σ(I)
graphite Rint = 0.048
ω and φ scans θmax = 28.6°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a) h = −20→20
Tmin = 0.975, Tmax = 0.981 k = −21→21
40376 measured reflections l = −19→21
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Refinement

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)] = 0.057 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184 H-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 parameters Δρmax = 0.37 e Å−3
96 restraints Δρmin = −0.34 e Å−3
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Special details

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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq Occ. (<1)
P1 0.80834 (3) 0.31741 (3) 0.17910 (4) 0.04635 (17)
O1 0.77840 (9) 0.32898 (10) 0.08683 (10) 0.0541 (4)
O2 0.75319 (10) 0.26971 (9) 0.23155 (10) 0.0544 (4)
O3 0.90074 (9) 0.28306 (9) 0.16739 (11) 0.0561 (4)
O4 0.82627 (10) 0.40839 (9) 0.20586 (10) 0.0548 (4)
C1 0.53071 (13) 0.35143 (13) −0.01505 (15) 0.0488 (5)
C2 0.54388 (14) 0.32741 (14) 0.06516 (15) 0.0533 (6)
H2 0.4972 0.3147 0.0968 0.064*
C3 0.62501 (14) 0.32170 (14) 0.10006 (15) 0.0522 (6)
H3 0.6325 0.3057 0.1547 0.063*
C4 0.69482 (13) 0.33985 (13) 0.05346 (14) 0.0450 (5)
C5 0.68692 (14) 0.36596 (13) −0.02816 (14) 0.0493 (5)
C6 0.60322 (14) 0.36998 (14) −0.05986 (15) 0.0543 (6)
H6 0.5952 0.3861 −0.1144 0.065*
C7 0.44112 (15) 0.35747 (16) −0.05561 (16) 0.0607 (6)
C8 0.4393 (6) 0.3024 (6) −0.1327 (6) 0.085 (3) 0.567 (14)
H8A 0.4402 0.2457 −0.1163 0.102* 0.567 (14)
H8B 0.4882 0.3139 −0.1649 0.102* 0.567 (14)
H8C 0.3883 0.3132 −0.1648 0.102* 0.567 (14)
C9 0.3724 (4) 0.3209 (9) 0.0000 (5) 0.107 (3) 0.567 (14)
H9A 0.3950 0.2733 0.0279 0.129* 0.567 (14)
H9B 0.3235 0.3054 −0.0332 0.129* 0.567 (14)
H9C 0.3562 0.3612 0.0397 0.129* 0.567 (14)
C10 0.4207 (7) 0.4443 (5) −0.0816 (8) 0.103 (3) 0.567 (14)
H10A 0.3932 0.4723 −0.0376 0.124* 0.567 (14)
H10B 0.3835 0.4434 −0.1294 0.124* 0.567 (14)
H10C 0.4724 0.4725 −0.0942 0.124* 0.567 (14)
C8A 0.4184 (10) 0.2826 (7) −0.1025 (11) 0.108 (5) 0.433 (14)
H8AA 0.4199 0.2360 −0.0663 0.130* 0.433 (14)
H8AB 0.4583 0.2746 −0.1454 0.130* 0.433 (14)
H8AC 0.3621 0.2885 −0.1263 0.130* 0.433 (14)
C9A 0.3777 (6) 0.3814 (12) 0.0089 (6) 0.108 (4) 0.433 (14)
H9AA 0.3743 0.3383 0.0491 0.129* 0.433 (14)
H9AB 0.3227 0.3897 −0.0169 0.129* 0.433 (14)
H9AC 0.3961 0.4313 0.0355 0.129* 0.433 (14)
C10A 0.4376 (8) 0.4308 (8) −0.1153 (8) 0.089 (4) 0.433 (14)
H10D 0.4383 0.4812 −0.0846 0.107* 0.433 (14)
H10E 0.3863 0.4279 −0.1487 0.107* 0.433 (14)
H10F 0.4861 0.4291 −0.1500 0.107* 0.433 (14)
C11 0.76410 (15) 0.38937 (16) −0.08056 (16) 0.0599 (6)
C12 0.8214 (2) 0.31473 (19) −0.0926 (2) 0.0890 (10)
H12A 0.8709 0.3310 −0.1219 0.107*
H12B 0.7907 0.2735 −0.1236 0.107*
H12C 0.8385 0.2927 −0.0399 0.107*
C13 0.81492 (18) 0.45868 (17) −0.0382 (2) 0.0806 (9)
H13A 0.8394 0.4390 0.0128 0.097*
H13B 0.7777 0.5041 −0.0277 0.097*
H13C 0.8595 0.4764 −0.0733 0.097*
C14 0.7358 (2) 0.4221 (3) −0.1651 (2) 0.1123 (13)
H14A 0.7848 0.4395 −0.1945 0.135*
H14B 0.6981 0.4680 −0.1584 0.135*
H14C 0.7067 0.3794 −0.1954 0.135*
C15 0.92470 (13) 0.19949 (12) 0.15720 (14) 0.0466 (5)
C16 0.86524 (15) 0.13759 (14) 0.16109 (16) 0.0573 (6)
H16 0.8079 0.1506 0.1657 0.069*
C17 0.89021 (16) 0.05613 (14) 0.15820 (16) 0.0589 (6)
H17 0.8492 0.0149 0.1601 0.071*
C18 0.97496 (15) 0.03491 (13) 0.15252 (14) 0.0525 (6)
C19 1.03290 (15) 0.09966 (13) 0.14503 (14) 0.0524 (6)
H19 1.0900 0.0863 0.1392 0.063*
C20 1.01107 (14) 0.18317 (13) 0.14575 (14) 0.0479 (5)
C21 1.00460 (17) −0.05547 (14) 0.15407 (17) 0.0639 (7)
C22 1.0388 (5) −0.0797 (3) 0.0717 (3) 0.098 (2) 0.668 (7)
H22A 1.0961 −0.0601 0.0675 0.118* 0.668 (7)
H22B 1.0038 −0.0560 0.0286 0.118* 0.668 (7)
H22C 1.0381 −0.1386 0.0667 0.118* 0.668 (7)
C23 1.0779 (5) −0.0663 (3) 0.2184 (4) 0.117 (3) 0.668 (7)
H23A 1.0990 −0.0133 0.2349 0.140* 0.668 (7)
H23B 1.1230 −0.0975 0.1947 0.140* 0.668 (7)
H23C 1.0572 −0.0949 0.2655 0.140* 0.668 (7)
C24 0.9340 (4) −0.1140 (3) 0.1769 (6) 0.130 (3) 0.668 (7)
H24A 0.9142 −0.1003 0.2305 0.156* 0.668 (7)
H24B 0.9553 −0.1694 0.1774 0.156* 0.668 (7)
H24C 0.8877 −0.1096 0.1373 0.156* 0.668 (7)
C22A 0.9980 (12) −0.0870 (8) 0.2385 (7) 0.115 (5) 0.332 (7)
H22D 1.0372 −0.0579 0.2743 0.138* 0.332 (7)
H22E 1.0115 −0.1446 0.2394 0.138* 0.332 (7)
H22F 0.9410 −0.0790 0.2569 0.138* 0.332 (7)
C23A 0.9422 (8) −0.1038 (6) 0.0956 (9) 0.114 (5) 0.332 (7)
H23D 0.9081 −0.0656 0.0639 0.136* 0.332 (7)
H23E 0.9059 −0.1379 0.1276 0.136* 0.332 (7)
H23F 0.9743 −0.1375 0.0592 0.136* 0.332 (7)
C24A 1.0915 (9) −0.0643 (8) 0.1216 (12) 0.128 (5) 0.332 (7)
H24D 1.1312 −0.0342 0.1559 0.154* 0.332 (7)
H24E 1.0923 −0.0432 0.0666 0.154* 0.332 (7)
H24F 1.1071 −0.1214 0.1215 0.154* 0.332 (7)
C25 1.07798 (15) 0.25155 (14) 0.13433 (17) 0.0602 (7)
C26 1.16553 (17) 0.21537 (19) 0.1140 (2) 0.0894 (10)
H26A 1.1867 0.1833 0.1597 0.107*
H26B 1.2046 0.2593 0.1034 0.107*
H26C 1.1599 0.1810 0.0661 0.107*
C27 1.08814 (17) 0.30289 (17) 0.2130 (2) 0.0766 (8)
H27A 1.1044 0.2677 0.2582 0.092*
H27B 1.0350 0.3292 0.2244 0.092*
H27C 1.1313 0.3439 0.2058 0.092*
C28 1.0509 (2) 0.30698 (17) 0.0608 (2) 0.0821 (9)
H28A 1.0922 0.3499 0.0544 0.099*
H28B 0.9962 0.3309 0.0708 0.099*
H28C 1.0473 0.2745 0.0115 0.099*
C29 0.83683 (13) 0.44192 (12) 0.28703 (14) 0.0461 (5)
C30 0.80912 (15) 0.39926 (14) 0.35457 (15) 0.0566 (6)
H30 0.7860 0.3469 0.3482 0.068*
C31 0.81596 (16) 0.43484 (14) 0.43200 (16) 0.0569 (6)
H31 0.7980 0.4054 0.4774 0.068*
C32 0.84884 (14) 0.51314 (14) 0.44336 (15) 0.0523 (6)
C33 0.87591 (14) 0.55355 (14) 0.37267 (15) 0.0524 (6)
H33 0.8981 0.6062 0.3791 0.063*
C34 0.87219 (13) 0.52098 (12) 0.29329 (14) 0.0470 (5)
C35 0.90342 (15) 0.56929 (13) 0.21791 (16) 0.0562 (6)
C36 0.97073 (17) 0.51997 (16) 0.17182 (19) 0.0753 (8)
H36A 0.9463 0.4690 0.1528 0.090*
H36B 1.0185 0.5088 0.2083 0.090*
H36C 0.9894 0.5513 0.1256 0.090*
C37 0.82689 (18) 0.58997 (16) 0.16050 (17) 0.0707 (7)
H37A 0.8464 0.6184 0.1129 0.085*
H37B 0.7877 0.6243 0.1891 0.085*
H37C 0.7987 0.5401 0.1437 0.085*
C38 0.9459 (2) 0.65100 (16) 0.2443 (2) 0.0808 (9)
H38A 0.9644 0.6798 0.1964 0.097*
H38B 0.9941 0.6398 0.2801 0.097*
H38C 0.9056 0.6842 0.2727 0.097*
C39 0.85283 (17) 0.55513 (16) 0.52831 (16) 0.0635 (7)
C40 0.9374 (2) 0.6003 (3) 0.5429 (2) 0.1156 (13)
H40A 0.9396 0.6226 0.5976 0.139*
H40B 0.9419 0.6441 0.5037 0.139*
H40C 0.9837 0.5625 0.5365 0.139*
C41 0.7845 (2) 0.6210 (3) 0.5294 (2) 0.1212 (15)
H41A 0.7293 0.5956 0.5258 0.145*
H41B 0.7910 0.6572 0.4834 0.145*
H41C 0.7898 0.6519 0.5796 0.145*
C42 0.8437 (3) 0.4962 (2) 0.5980 (2) 0.1315 (16)
H42A 0.7873 0.4734 0.5963 0.158*
H42B 0.8533 0.5246 0.6492 0.158*
H42C 0.8847 0.4528 0.5933 0.158*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
P1 0.0426 (3) 0.0424 (3) 0.0536 (4) 0.0009 (2) −0.0056 (2) 0.0007 (3)
O1 0.0401 (8) 0.0708 (10) 0.0512 (10) 0.0022 (7) −0.0023 (7) 0.0024 (8)
O2 0.0534 (9) 0.0509 (8) 0.0583 (11) −0.0046 (7) −0.0054 (7) 0.0050 (7)
O3 0.0408 (8) 0.0416 (8) 0.0853 (12) 0.0017 (6) −0.0073 (7) −0.0025 (8)
O4 0.0687 (10) 0.0426 (8) 0.0530 (10) −0.0014 (7) 0.0015 (8) −0.0003 (7)
C1 0.0449 (12) 0.0515 (12) 0.0497 (15) −0.0002 (10) −0.0052 (10) −0.0044 (10)
C2 0.0424 (12) 0.0627 (14) 0.0550 (16) −0.0018 (10) 0.0024 (10) 0.0029 (11)
C3 0.0459 (12) 0.0635 (14) 0.0470 (14) 0.0016 (10) −0.0003 (10) 0.0058 (11)
C4 0.0402 (11) 0.0466 (11) 0.0481 (14) 0.0005 (9) −0.0034 (9) −0.0028 (10)
C5 0.0484 (12) 0.0510 (12) 0.0484 (15) −0.0038 (10) 0.0012 (10) −0.0005 (10)
C6 0.0534 (13) 0.0635 (14) 0.0455 (15) −0.0032 (11) −0.0058 (10) 0.0022 (11)
C7 0.0475 (13) 0.0712 (16) 0.0624 (17) −0.0014 (11) −0.0130 (11) −0.0046 (13)
C8 0.063 (4) 0.103 (6) 0.086 (5) −0.008 (3) −0.029 (3) −0.020 (4)
C9 0.051 (3) 0.177 (8) 0.092 (5) −0.024 (4) −0.012 (3) 0.016 (5)
C10 0.077 (5) 0.067 (4) 0.163 (8) 0.015 (3) −0.036 (5) −0.014 (5)
C8A 0.088 (7) 0.074 (5) 0.161 (10) −0.010 (5) −0.042 (7) −0.019 (6)
C9A 0.047 (4) 0.167 (9) 0.109 (6) 0.027 (6) −0.009 (4) −0.002 (6)
C10A 0.061 (5) 0.096 (7) 0.109 (7) 0.016 (4) −0.037 (5) 0.012 (6)
C11 0.0535 (13) 0.0757 (16) 0.0509 (16) −0.0086 (12) 0.0065 (11) 0.0057 (12)
C12 0.084 (2) 0.091 (2) 0.094 (2) −0.0067 (17) 0.0424 (18) −0.0130 (17)
C13 0.0713 (18) 0.0772 (18) 0.094 (2) −0.0210 (15) 0.0206 (16) 0.0024 (16)
C14 0.087 (2) 0.185 (4) 0.065 (2) −0.025 (2) 0.0074 (17) 0.040 (2)
C15 0.0464 (12) 0.0394 (10) 0.0536 (14) 0.0013 (9) −0.0089 (10) −0.0027 (9)
C16 0.0442 (12) 0.0505 (13) 0.0766 (18) −0.0010 (10) −0.0080 (11) −0.0065 (12)
C17 0.0619 (15) 0.0447 (12) 0.0702 (18) −0.0076 (11) 0.0007 (12) −0.0071 (11)
C18 0.0661 (15) 0.0438 (11) 0.0477 (15) 0.0012 (10) 0.0044 (11) −0.0045 (10)
C19 0.0523 (13) 0.0500 (12) 0.0552 (15) 0.0089 (10) 0.0056 (10) −0.0016 (11)
C20 0.0495 (12) 0.0464 (11) 0.0478 (14) 0.0005 (10) 0.0010 (10) −0.0014 (10)
C21 0.0820 (18) 0.0429 (12) 0.0674 (18) 0.0071 (12) 0.0121 (14) −0.0018 (12)
C22 0.154 (5) 0.060 (3) 0.082 (4) 0.037 (3) 0.010 (3) −0.013 (2)
C23 0.159 (6) 0.068 (3) 0.122 (5) 0.045 (3) −0.043 (4) 0.000 (3)
C24 0.126 (5) 0.055 (3) 0.211 (8) 0.000 (3) 0.045 (5) 0.034 (4)
C22A 0.157 (9) 0.086 (6) 0.103 (8) 0.036 (7) 0.008 (7) 0.026 (6)
C23A 0.142 (9) 0.061 (5) 0.136 (9) 0.021 (6) −0.021 (7) −0.029 (6)
C24A 0.146 (9) 0.082 (6) 0.160 (10) 0.041 (6) 0.048 (7) 0.014 (7)
C25 0.0506 (13) 0.0508 (12) 0.0797 (19) −0.0050 (10) 0.0095 (12) −0.0014 (12)
C26 0.0595 (17) 0.0759 (18) 0.134 (3) −0.0055 (14) 0.0286 (18) 0.0014 (18)
C27 0.0587 (16) 0.0699 (16) 0.101 (2) −0.0147 (13) −0.0051 (15) −0.0120 (16)
C28 0.090 (2) 0.0639 (16) 0.094 (2) −0.0081 (15) 0.0217 (17) 0.0146 (15)
C29 0.0455 (11) 0.0422 (11) 0.0504 (14) 0.0043 (9) −0.0021 (9) −0.0021 (10)
C30 0.0662 (15) 0.0452 (12) 0.0583 (17) −0.0046 (11) −0.0019 (12) 0.0020 (11)
C31 0.0661 (15) 0.0532 (13) 0.0512 (16) −0.0006 (11) 0.0000 (11) 0.0060 (11)
C32 0.0469 (12) 0.0512 (12) 0.0584 (16) 0.0073 (10) −0.0053 (10) −0.0033 (11)
C33 0.0476 (12) 0.0447 (11) 0.0646 (17) −0.0004 (9) −0.0014 (11) −0.0043 (11)
C34 0.0404 (11) 0.0435 (11) 0.0570 (15) 0.0035 (9) 0.0000 (9) 0.0001 (10)
C35 0.0597 (14) 0.0440 (11) 0.0653 (17) −0.0014 (10) 0.0105 (12) −0.0002 (11)
C36 0.0670 (16) 0.0689 (16) 0.091 (2) −0.0023 (13) 0.0262 (15) −0.0037 (15)
C37 0.0847 (19) 0.0614 (15) 0.0661 (19) 0.0085 (14) 0.0052 (14) 0.0117 (13)
C38 0.100 (2) 0.0547 (14) 0.089 (2) −0.0185 (15) 0.0223 (17) −0.0017 (14)
C39 0.0652 (16) 0.0664 (15) 0.0586 (17) 0.0062 (13) −0.0038 (12) −0.0064 (13)
C40 0.112 (3) 0.143 (3) 0.092 (3) −0.027 (3) −0.007 (2) −0.048 (2)
C41 0.116 (3) 0.148 (3) 0.099 (3) 0.054 (3) 0.000 (2) −0.044 (3)
C42 0.229 (5) 0.100 (3) 0.065 (2) −0.021 (3) −0.008 (3) −0.002 (2)
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Geometric parameters (Å, °)

P1—O2 1.4559 (16) C21—C24 1.516 (5)
P1—O4 1.5655 (16) C21—C23 1.543 (6)
P1—O3 1.5712 (15) C21—C23A 1.559 (10)
P1—O1 1.5713 (17) C22—H22A 0.96
O1—C4 1.417 (3) C22—H22B 0.96
O3—C15 1.421 (2) C22—H22C 0.96
O4—C29 1.434 (3) C23—H23A 0.96
C1—C2 1.372 (3) C23—H23B 0.96
C1—C6 1.401 (3) C23—H23C 0.96
C1—C7 1.540 (3) C24—H24A 0.96
C2—C3 1.384 (3) C24—H24B 0.96
C2—H2 0.93 C24—H24C 0.96
C3—C4 1.382 (3) C22A—H22D 0.96
C3—H3 0.93 C22A—H22E 0.96
C4—C5 1.396 (3) C22A—H22F 0.96
C5—C6 1.400 (3) C23A—H23D 0.96
C5—C11 1.548 (3) C23A—H23E 0.96
C6—H6 0.93 C23A—H23F 0.96
C7—C8A 1.475 (9) C24A—H24D 0.96
C7—C10 1.506 (9) C24A—H24E 0.96
C7—C9A 1.517 (8) C24A—H24F 0.96
C7—C10A 1.538 (9) C25—C27 1.533 (4)
C7—C8 1.540 (8) C25—C26 1.540 (3)
C7—C9 1.546 (7) C25—C28 1.548 (4)
C8—H8A 0.96 C26—H26A 0.96
C8—H8B 0.96 C26—H26B 0.96
C8—H8C 0.96 C26—H26C 0.96
C9—H9A 0.96 C27—H27A 0.96
C9—H9B 0.96 C27—H27B 0.96
C9—H9C 0.96 C27—H27C 0.96
C10—H10A 0.96 C28—H28A 0.96
C10—H10B 0.96 C28—H28B 0.96
C10—H10C 0.96 C28—H28C 0.96
C8A—H8AA 0.96 C29—C30 1.380 (3)
C8A—H8AB 0.96 C29—C34 1.403 (3)
C8A—H8AC 0.96 C30—C31 1.387 (3)
C9A—H9AA 0.96 C30—H30 0.9300
C9A—H9AB 0.96 C31—C32 1.385 (3)
C9A—H9AC 0.96 C31—H31 0.9300
C10A—H10D 0.96 C32—C33 1.400 (3)
C10A—H10E 0.96 C32—C39 1.541 (3)
C10A—H10F 0.96 C33—C34 1.395 (3)
C11—C12 1.527 (4) C33—H33 0.9300
C11—C14 1.528 (4) C34—C35 1.547 (3)
C11—C13 1.533 (4) C35—C36 1.538 (3)
C12—H12A 0.96 C35—C37 1.538 (4)
C12—H12B 0.96 C35—C38 1.542 (3)
C12—H12C 0.96 C36—H36A 0.96
C13—H13A 0.96 C36—H36B 0.96
C13—H13B 0.96 C36—H36C 0.96
C13—H13C 0.96 C37—H37A 0.96
C14—H14A 0.96 C37—H37B 0.96
C14—H14B 0.96 C37—H37C 0.96
C14—H14C 0.96 C38—H38A 0.96
C15—C16 1.376 (3) C38—H38B 0.96
C15—C20 1.399 (3) C38—H38C 0.96
C16—C17 1.383 (3) C39—C42 1.494 (4)
C16—H16 0.9300 C39—C41 1.517 (4)
C17—C18 1.380 (3) C39—C40 1.530 (4)
C17—H17 0.9300 C40—H40A 0.96
C18—C19 1.399 (3) C40—H40B 0.96
C18—C21 1.542 (3) C40—H40C 0.96
C19—C20 1.401 (3) C41—H41A 0.96
C19—H19 0.9300 C41—H41B 0.96
C20—C25 1.545 (3) C41—H41C 0.96
C21—C22A 1.472 (9) C42—H42A 0.96
C21—C24A 1.483 (10) C42—H42B 0.96
C21—C22 1.509 (5) C42—H42C 0.96
O2—P1—O4 116.48 (9) C22—C21—C23 107.2 (4)
O2—P1—O3 116.59 (9) C24—C21—C23 107.4 (5)
O4—P1—O3 102.13 (8) C18—C21—C23 109.8 (3)
O2—P1—O1 117.14 (9) C22A—C21—C23A 109.6 (8)
O4—P1—O1 101.49 (9) C24A—C21—C23A 107.6 (9)
O3—P1—O1 100.36 (9) C22—C21—C23A 63.8 (6)
C4—O1—P1 129.05 (14) C24—C21—C23A 51.8 (6)
C15—O3—P1 127.04 (13) C18—C21—C23A 106.6 (4)
C29—O4—P1 129.11 (14) C23—C21—C23A 143.2 (5)
C2—C1—C6 116.9 (2) C21—C22—H22A 109.5
C2—C1—C7 122.5 (2) C21—C22—H22B 109.5
C6—C1—C7 120.6 (2) H22A—C22—H22B 109.5
C1—C2—C3 121.5 (2) C21—C22—H22C 109.5
C1—C2—H2 119.3 H22A—C22—H22C 109.5
C3—C2—H2 119.3 H22B—C22—H22C 109.5
C4—C3—C2 119.7 (2) C21—C23—H23A 109.5
C4—C3—H3 120.1 C21—C23—H23B 109.5
C2—C3—H3 120.1 H23A—C23—H23B 109.5
C3—C4—C5 122.4 (2) C21—C23—H23C 109.5
C3—C4—O1 120.2 (2) H23A—C23—H23C 109.5
C5—C4—O1 117.33 (18) H23B—C23—H23C 109.5
C4—C5—C6 114.98 (19) C21—C24—H24A 109.5
C4—C5—C11 123.2 (2) C21—C24—H24B 109.5
C6—C5—C11 121.8 (2) H24A—C24—H24B 109.5
C5—C6—C1 124.5 (2) C21—C24—H24C 109.5
C5—C6—H6 117.8 H24A—C24—H24C 109.5
C1—C6—H6 117.8 H24B—C24—H24C 109.5
C8A—C7—C10 125.6 (7) C21—C22A—H22D 109.5
C8A—C7—C9A 114.5 (7) C21—C22A—H22E 109.5
C10—C7—C9A 79.3 (6) H22D—C22A—H22E 109.5
C8A—C7—C10A 108.0 (8) C21—C22A—H22F 109.5
C9A—C7—C10A 103.0 (6) H22D—C22A—H22F 109.5
C10—C7—C8 108.6 (6) H22E—C22A—H22F 109.5
C9A—C7—C8 135.6 (6) C21—C23A—H23D 109.5
C10A—C7—C8 86.4 (6) C21—C23A—H23E 109.5
C8A—C7—C1 112.0 (6) H23D—C23A—H23E 109.5
C10—C7—C1 111.4 (5) C21—C23A—H23F 109.5
C9A—C7—C1 109.2 (4) H23D—C23A—H23F 109.5
C10A—C7—C1 109.7 (5) H23E—C23A—H23F 109.5
C8—C7—C1 107.9 (4) C21—C24A—H24D 109.5
C8A—C7—C9 79.7 (6) C21—C24A—H24E 109.5
C10—C7—C9 112.2 (5) H24D—C24A—H24E 109.5
C10A—C7—C9 130.9 (6) C21—C24A—H24F 109.5
C8—C7—C9 104.7 (5) H24D—C24A—H24F 109.5
C1—C7—C9 111.6 (3) H24E—C24A—H24F 109.5
C7—C8—H8A 109.5 C27—C25—C26 108.3 (2)
C7—C8—H8B 109.5 C27—C25—C20 110.3 (2)
H8A—C8—H8B 109.5 C26—C25—C20 111.4 (2)
C7—C8—H8C 109.5 C27—C25—C28 110.4 (2)
H8A—C8—H8C 109.5 C26—C25—C28 106.5 (2)
H8B—C8—H8C 109.5 C20—C25—C28 109.8 (2)
C7—C9—H9A 109.5 C25—C26—H26A 109.5
C7—C9—H9B 109.5 C25—C26—H26B 109.5
H9A—C9—H9B 109.5 H26A—C26—H26B 109.5
C7—C9—H9C 109.5 C25—C26—H26C 109.5
H9A—C9—H9C 109.5 H26A—C26—H26C 109.5
H9B—C9—H9C 109.5 H26B—C26—H26C 109.5
C7—C10—H10A 109.5 C25—C27—H27A 109.5
C7—C10—H10B 109.5 C25—C27—H27B 109.5
H10A—C10—H10B 109.5 H27A—C27—H27B 109.5
C7—C10—H10C 109.5 C25—C27—H27C 109.5
H10A—C10—H10C 109.5 H27A—C27—H27C 109.5
H10B—C10—H10C 109.5 H27B—C27—H27C 109.5
C7—C8A—H8AA 109.5 C25—C28—H28A 109.5
C7—C8A—H8AB 109.5 C25—C28—H28B 109.5
H8AA—C8A—H8AB 109.5 H28A—C28—H28B 109.5
C7—C8A—H8AC 109.5 C25—C28—H28C 109.5
H8AA—C8A—H8AC 109.5 H28A—C28—H28C 109.5
H8AB—C8A—H8AC 109.5 H28B—C28—H28C 109.5
C7—C9A—H9AA 109.5 C30—C29—C34 122.4 (2)
C7—C9A—H9AB 109.5 C30—C29—O4 120.71 (19)
H9AA—C9A—H9AB 109.5 C34—C29—O4 116.79 (19)
C7—C9A—H9AC 109.5 C29—C30—C31 119.6 (2)
H9AA—C9A—H9AC 109.5 C29—C30—H30 120.2
H9AB—C9A—H9AC 109.5 C31—C30—H30 120.2
C7—C10A—H10D 109.5 C32—C31—C30 121.6 (2)
C7—C10A—H10E 109.5 C32—C31—H31 119.2
H10D—C10A—H10E 109.5 C30—C31—H31 119.2
C7—C10A—H10F 109.5 C31—C32—C33 116.3 (2)
H10D—C10A—H10F 109.5 C31—C32—C39 122.2 (2)
H10E—C10A—H10F 109.5 C33—C32—C39 121.5 (2)
C12—C11—C14 108.6 (3) C34—C33—C32 125.1 (2)
C12—C11—C13 109.9 (2) C34—C33—H33 117.4
C14—C11—C13 106.4 (2) C32—C33—H33 117.4
C12—C11—C5 110.4 (2) C33—C34—C29 114.9 (2)
C14—C11—C5 111.6 (2) C33—C34—C35 122.29 (19)
C13—C11—C5 109.8 (2) C29—C34—C35 122.8 (2)
C11—C12—H12A 109.5 C36—C35—C37 110.7 (2)
C11—C12—H12B 109.5 C36—C35—C38 106.7 (2)
H12A—C12—H12B 109.5 C37—C35—C38 107.8 (2)
C11—C12—H12C 109.5 C36—C35—C34 111.00 (19)
H12A—C12—H12C 109.5 C37—C35—C34 109.43 (19)
H12B—C12—H12C 109.5 C38—C35—C34 111.2 (2)
C11—C13—H13A 109.5 C35—C36—H36A 109.5
C11—C13—H13B 109.5 C35—C36—H36B 109.5
H13A—C13—H13B 109.5 H36A—C36—H36B 109.5
C11—C13—H13C 109.5 C35—C36—H36C 109.5
H13A—C13—H13C 109.5 H36A—C36—H36C 109.5
H13B—C13—H13C 109.5 H36B—C36—H36C 109.5
C11—C14—H14A 109.5 C35—C37—H37A 109.5
C11—C14—H14B 109.5 C35—C37—H37B 109.5
H14A—C14—H14B 109.5 H37A—C37—H37B 109.5
C11—C14—H14C 109.5 C35—C37—H37C 109.5
H14A—C14—H14C 109.5 H37A—C37—H37C 109.5
H14B—C14—H14C 109.5 H37B—C37—H37C 109.5
C16—C15—C20 121.93 (19) C35—C38—H38A 109.5
C16—C15—O3 120.82 (19) C35—C38—H38B 109.5
C20—C15—O3 117.23 (18) H38A—C38—H38B 109.5
C15—C16—C17 120.4 (2) C35—C38—H38C 109.5
C15—C16—H16 119.8 H38A—C38—H38C 109.5
C17—C16—H16 119.8 H38B—C38—H38C 109.5
C18—C17—C16 121.1 (2) C42—C39—C41 111.2 (3)
C18—C17—H17 119.4 C42—C39—C40 106.9 (3)
C16—C17—H17 119.4 C41—C39—C40 105.7 (3)
C17—C18—C19 116.6 (2) C42—C39—C32 113.2 (2)
C17—C18—C21 121.9 (2) C41—C39—C32 108.2 (2)
C19—C18—C21 121.5 (2) C40—C39—C32 111.4 (2)
C18—C19—C20 124.7 (2) C39—C40—H40A 109.5
C18—C19—H19 117.7 C39—C40—H40B 109.5
C20—C19—H19 117.7 H40A—C40—H40B 109.5
C15—C20—C19 115.04 (19) C39—C40—H40C 109.5
C15—C20—C25 122.98 (19) H40A—C40—H40C 109.5
C19—C20—C25 121.98 (19) H40B—C40—H40C 109.5
C22A—C21—C24A 112.8 (9) C39—C41—H41A 109.5
C22A—C21—C22 140.6 (5) C39—C41—H41B 109.5
C24A—C21—C22 46.0 (7) H41A—C41—H41B 109.5
C22A—C21—C24 58.8 (7) C39—C41—H41C 109.5
C24A—C21—C24 135.4 (6) H41A—C41—H41C 109.5
C22—C21—C24 109.5 (4) H41B—C41—H41C 109.5
C22A—C21—C18 108.6 (5) C39—C42—H42A 109.5
C24A—C21—C18 111.5 (5) C39—C42—H42B 109.5
C22—C21—C18 110.5 (3) H42A—C42—H42B 109.5
C24—C21—C18 112.4 (3) C39—C42—H42C 109.5
C22A—C21—C23 53.0 (6) H42A—C42—H42C 109.5
C24A—C21—C23 63.5 (8) H42B—C42—H42C 109.5
O2—P1—O1—C4 36.4 (2) C16—C15—C20—C19 −4.7 (3)
O4—P1—O1—C4 −91.55 (18) O3—C15—C20—C19 173.3 (2)
O3—P1—O1—C4 163.67 (17) C16—C15—C20—C25 175.0 (2)
O2—P1—O3—C15 39.9 (2) O3—C15—C20—C25 −6.9 (3)
O4—P1—O3—C15 168.08 (18) C18—C19—C20—C15 1.8 (4)
O1—P1—O3—C15 −87.66 (19) C18—C19—C20—C25 −178.0 (2)
O2—P1—O4—C29 35.9 (2) C17—C18—C21—C22A −72.9 (8)
O3—P1—O4—C29 −92.31 (18) C19—C18—C21—C22A 107.2 (8)
O1—P1—O4—C29 164.32 (17) C17—C18—C21—C24A 162.2 (9)
C6—C1—C2—C3 −0.1 (3) C19—C18—C21—C24A −17.6 (9)
C7—C1—C2—C3 179.4 (2) C17—C18—C21—C22 112.7 (4)
C1—C2—C3—C4 −0.5 (3) C19—C18—C21—C22 −67.1 (4)
C2—C3—C4—C5 1.5 (3) C17—C18—C21—C24 −9.9 (6)
C2—C3—C4—O1 −175.8 (2) C19—C18—C21—C24 170.3 (5)
P1—O1—C4—C3 −15.8 (3) C17—C18—C21—C23 −129.3 (4)
P1—O1—C4—C5 166.79 (16) C19—C18—C21—C23 50.9 (5)
C3—C4—C5—C6 −1.8 (3) C17—C18—C21—C23A 45.0 (7)
O1—C4—C5—C6 175.57 (18) C19—C18—C21—C23A −134.8 (7)
C3—C4—C5—C11 177.9 (2) C15—C20—C25—C27 65.6 (3)
O1—C4—C5—C11 −4.7 (3) C19—C20—C25—C27 −114.6 (3)
C4—C5—C6—C1 1.2 (3) C15—C20—C25—C26 −174.0 (2)
C11—C5—C6—C1 −178.5 (2) C19—C20—C25—C26 5.8 (4)
C2—C1—C6—C5 −0.3 (3) C15—C20—C25—C28 −56.2 (3)
C7—C1—C6—C5 −179.8 (2) C19—C20—C25—C28 123.5 (2)
C2—C1—C7—C8A −96.1 (8) P1—O4—C29—C30 −18.0 (3)
C6—C1—C7—C8A 83.3 (8) P1—O4—C29—C34 165.17 (15)
C2—C1—C7—C10 117.5 (6) C34—C29—C30—C31 0.0 (3)
C6—C1—C7—C10 −63.0 (6) O4—C29—C30—C31 −176.6 (2)
C2—C1—C7—C9A 31.8 (8) C29—C30—C31—C32 1.0 (4)
C6—C1—C7—C9A −148.8 (8) C30—C31—C32—C33 −1.0 (3)
C2—C1—C7—C10A 144.0 (7) C30—C31—C32—C39 177.0 (2)
C6—C1—C7—C10A −36.6 (7) C31—C32—C33—C34 −0.1 (3)
C2—C1—C7—C8 −123.4 (5) C39—C32—C33—C34 −178.1 (2)
C6—C1—C7—C8 56.1 (5) C32—C33—C34—C29 1.0 (3)
C2—C1—C7—C9 −8.8 (7) C32—C33—C34—C35 −180.0 (2)
C6—C1—C7—C9 170.6 (6) C30—C29—C34—C33 −1.0 (3)
C4—C5—C11—C12 63.7 (3) O4—C29—C34—C33 175.77 (18)
C6—C5—C11—C12 −116.6 (3) C30—C29—C34—C35 −180.0 (2)
C4—C5—C11—C14 −175.4 (3) O4—C29—C34—C35 −3.2 (3)
C6—C5—C11—C14 4.3 (4) C33—C34—C35—C36 124.4 (2)
C4—C5—C11—C13 −57.7 (3) C29—C34—C35—C36 −56.7 (3)
C6—C5—C11—C13 122.0 (3) C33—C34—C35—C37 −113.1 (2)
P1—O3—C15—C16 −3.4 (3) C29—C34—C35—C37 65.8 (3)
P1—O3—C15—C20 178.51 (16) C33—C34—C35—C38 5.8 (3)
C20—C15—C16—C17 3.6 (4) C29—C34—C35—C38 −175.3 (2)
O3—C15—C16—C17 −174.4 (2) C31—C32—C39—C42 17.5 (4)
C15—C16—C17—C18 0.9 (4) C33—C32—C39—C42 −164.6 (3)
C16—C17—C18—C19 −3.6 (4) C31—C32—C39—C41 −106.1 (3)
C16—C17—C18—C21 176.5 (2) C33—C32—C39—C41 71.7 (3)
C17—C18—C19—C20 2.3 (4) C31—C32—C39—C40 138.1 (3)
C21—C18—C19—C20 −177.9 (2) C33—C32—C39—C40 −44.0 (3)
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Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A 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
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5107).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810029673/ci5107sup1.cif

e-66-o2207-sup1.cif (37.6KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029673/ci5107Isup2.hkl

e-66-o2207-Isup2.hkl (495KB, hkl)

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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