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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): o2207–o2208.
Published online 2010 August 4. doi:  10.1107/S1600536810029673
PMCID: PMC3008051

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

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 [triangle]); Chadha (1976 [triangle]); Kulkarni et al. (2008 [triangle]); Sahare et al. (2008 [triangle]); Rastogi et al. (2009 [triangle]). For the geometry of the 2,4-di-tert-butyl­phenyl group, see: Janse van Rensburg et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2207-scheme1.jpg

Experimental

Crystal data

  • C42H63O4P
  • M r = 662.89
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2207-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: SAINT (Bruker, 2004 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

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.
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

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

Bruker Kappa APEXII CCD area-detector diffractometer10329 independent reflections
Radiation source: fine-focus sealed tube5669 reflections with I > 2σ(I)
graphiteRint = 0.048
ω and [var phi] scansθmax = 28.6°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)h = −20→20
Tmin = 0.975, Tmax = 0.981k = −21→21
40376 measured reflectionsl = −19→21

Refinement

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 = 1.02w = 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

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.

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

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)
H60.59520.3861−0.11440.065*
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)
H8A0.44020.2457−0.11630.102*0.567 (14)
H8B0.48820.3139−0.16490.102*0.567 (14)
H8C0.38830.3132−0.16480.102*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)
H9B0.32350.3054−0.03320.129*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)
H10A0.39320.4723−0.03760.124*0.567 (14)
H10B0.38350.4434−0.12940.124*0.567 (14)
H10C0.47240.4725−0.09420.124*0.567 (14)
C8A0.4184 (10)0.2826 (7)−0.1025 (11)0.108 (5)0.433 (14)
H8AA0.41990.2360−0.06630.130*0.433 (14)
H8AB0.45830.2746−0.14540.130*0.433 (14)
H8AC0.36210.2885−0.12630.130*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)
H9AB0.32270.3897−0.01690.129*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)
H10D0.43830.4812−0.08460.107*0.433 (14)
H10E0.38630.4279−0.14870.107*0.433 (14)
H10F0.48610.4291−0.15000.107*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)
H12A0.87090.3310−0.12190.107*
H12B0.79070.2735−0.12360.107*
H12C0.83850.2927−0.03990.107*
C130.81492 (18)0.45868 (17)−0.0382 (2)0.0806 (9)
H13A0.83940.43900.01280.097*
H13B0.77770.5041−0.02770.097*
H13C0.85950.4764−0.07330.097*
C140.7358 (2)0.4221 (3)−0.1651 (2)0.1123 (13)
H14A0.78480.4395−0.19450.135*
H14B0.69810.4680−0.15840.135*
H14C0.70670.3794−0.19540.135*
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)
H22A1.0961−0.06010.06750.118*0.668 (7)
H22B1.0038−0.05600.02860.118*0.668 (7)
H22C1.0381−0.13860.06670.118*0.668 (7)
C231.0779 (5)−0.0663 (3)0.2184 (4)0.117 (3)0.668 (7)
H23A1.0990−0.01330.23490.140*0.668 (7)
H23B1.1230−0.09750.19470.140*0.668 (7)
H23C1.0572−0.09490.26550.140*0.668 (7)
C240.9340 (4)−0.1140 (3)0.1769 (6)0.130 (3)0.668 (7)
H24A0.9142−0.10030.23050.156*0.668 (7)
H24B0.9553−0.16940.17740.156*0.668 (7)
H24C0.8877−0.10960.13730.156*0.668 (7)
C22A0.9980 (12)−0.0870 (8)0.2385 (7)0.115 (5)0.332 (7)
H22D1.0372−0.05790.27430.138*0.332 (7)
H22E1.0115−0.14460.23940.138*0.332 (7)
H22F0.9410−0.07900.25690.138*0.332 (7)
C23A0.9422 (8)−0.1038 (6)0.0956 (9)0.114 (5)0.332 (7)
H23D0.9081−0.06560.06390.136*0.332 (7)
H23E0.9059−0.13790.12760.136*0.332 (7)
H23F0.9743−0.13750.05920.136*0.332 (7)
C24A1.0915 (9)−0.0643 (8)0.1216 (12)0.128 (5)0.332 (7)
H24D1.1312−0.03420.15590.154*0.332 (7)
H24E1.0923−0.04320.06660.154*0.332 (7)
H24F1.1071−0.12140.12150.154*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)

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, °)

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—C19−4.7 (3)
O4—P1—O1—C4−91.55 (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—C25−6.9 (3)
O4—P1—O3—C15168.08 (18)C18—C19—C20—C151.8 (4)
O1—P1—O3—C15−87.66 (19)C18—C19—C20—C25−178.0 (2)
O2—P1—O4—C2935.9 (2)C17—C18—C21—C22A−72.9 (8)
O3—P1—O4—C29−92.31 (18)C19—C18—C21—C22A107.2 (8)
O1—P1—O4—C29164.32 (17)C17—C18—C21—C24A162.2 (9)
C6—C1—C2—C3−0.1 (3)C19—C18—C21—C24A−17.6 (9)
C7—C1—C2—C3179.4 (2)C17—C18—C21—C22112.7 (4)
C1—C2—C3—C4−0.5 (3)C19—C18—C21—C22−67.1 (4)
C2—C3—C4—C51.5 (3)C17—C18—C21—C24−9.9 (6)
C2—C3—C4—O1−175.8 (2)C19—C18—C21—C24170.3 (5)
P1—O1—C4—C3−15.8 (3)C17—C18—C21—C23−129.3 (4)
P1—O1—C4—C5166.79 (16)C19—C18—C21—C2350.9 (5)
C3—C4—C5—C6−1.8 (3)C17—C18—C21—C23A45.0 (7)
O1—C4—C5—C6175.57 (18)C19—C18—C21—C23A−134.8 (7)
C3—C4—C5—C11177.9 (2)C15—C20—C25—C2765.6 (3)
O1—C4—C5—C11−4.7 (3)C19—C20—C25—C27−114.6 (3)
C4—C5—C6—C11.2 (3)C15—C20—C25—C26−174.0 (2)
C11—C5—C6—C1−178.5 (2)C19—C20—C25—C265.8 (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—C28123.5 (2)
C2—C1—C7—C8A−96.1 (8)P1—O4—C29—C30−18.0 (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—C10−63.0 (6)O4—C29—C30—C31−176.6 (2)
C2—C1—C7—C9A31.8 (8)C29—C30—C31—C321.0 (4)
C6—C1—C7—C9A−148.8 (8)C30—C31—C32—C33−1.0 (3)
C2—C1—C7—C10A144.0 (7)C30—C31—C32—C39177.0 (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—C856.1 (5)C32—C33—C34—C291.0 (3)
C2—C1—C7—C9−8.8 (7)C32—C33—C34—C35−180.0 (2)
C6—C1—C7—C9170.6 (6)C30—C29—C34—C33−1.0 (3)
C4—C5—C11—C1263.7 (3)O4—C29—C34—C33175.77 (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—C144.3 (4)C33—C34—C35—C36124.4 (2)
C4—C5—C11—C13−57.7 (3)C29—C34—C35—C36−56.7 (3)
C6—C5—C11—C13122.0 (3)C33—C34—C35—C37−113.1 (2)
P1—O3—C15—C16−3.4 (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—C38−175.3 (2)
O3—C15—C16—C17−174.4 (2)C31—C32—C39—C4217.5 (4)
C15—C16—C17—C180.9 (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—C21176.5 (2)C33—C32—C39—C4171.7 (3)
C17—C18—C19—C202.3 (4)C31—C32—C39—C40138.1 (3)
C21—C18—C19—C20−177.9 (2)C33—C32—C39—C40−44.0 (3)

Hydrogen-bond geometry (Å, °)

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

Footnotes

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

References

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