Tris(2,4-di-tert-butyl-phen-yl) phosphate.

The title compound, C(42)H(63)O(4)P, 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 intra-molecular C-H⋯O inter-actions are observed in the mol-ecular 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 ▶).

Experimental

Crystal data

C42H63O4P

M = 662.89

Monoclinic,

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 ▶).

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

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

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

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

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.

	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*

	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)

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)

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

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