3,4-Dibromo-2,5-bis-[(dieth-oxy-phosphor-yl)meth-yl]-1-phenyl-sulfonyl-1H-pyrrole.

In the title compound, C(20)H(29)Br(2)NO(8)P(2)S, the pyrrole ring is essentially planar, with a maximum deviation of 0.013 (3) Å for a C atom. The pyrrole ring is almost orthogonal to the sulfonyl-bound phenyl ring, with a dihedral angle 88.5 (2)°. Both P atoms exhibit distorted tetra-hedral configurations with O-P-O angles widened and O-P-C angles narrowed from the ideal tetra-hedral value. In the crystal, mol-ecules are linked into centrosymmetric dimers via C-H⋯O inter-actions, resulting in R(2) (2)(10) graph-set motifs which are further consolidated by R(2) (2)(13) graph-set ring motifs via C-H⋯O inter-actions, further resulting in chains of mol-ecules running parallel to the c axis; a phosphono O atom is involved in bifurcated hydrogen bonding. All the eth-oxy groups are disordered over two positions each with unequal site-occupancy factors.

Related literature

For a related structure, see: Seshadri et al. (2009 ▶). For applications of pyrrole derivatives, see: Faulkner (2002 ▶); Banwell et al. (2006 ▶); Fabio et al. (2007 ▶). For comparison of mol­ecular dimensions, see: pan class="Chemical">Bassindale (1984 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C20H29Br2NO8P2S

M = 665.26

Monoclinic,

a = 9.6524 (2) Å

b = 17.5137 (5) Å

c = 15.8965 (4) Å

β = 95.506 (1)°

V = 2674.89 (12) Å3

Z = 4

Mo Kα radiation

μ = 3.27 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.440, T max = 0.561

34672 measured reflections

8138 independent reflections

4819 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.121

S = 1.00

8138 reflections

355 parameters

20 restraints

H-atom parameters constrained

Δρmax = 0.79 e Å−3

Δρmin = −0.76 e Å−3

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811030273/pv2427sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030273/pv2427Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811030273/pv2427Isup3.cml

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

C20H29Br2NO8P2S	F(000) = 1344
Mr = 665.26	Dx = 1.652 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8138 reflections
a = 9.6524 (2) Å	θ = 2.3–30.5°
b = 17.5137 (5) Å	µ = 3.27 mm−1
c = 15.8965 (4) Å	T = 293 K
β = 95.506 (1)°	Block, colourless
V = 2674.89 (12) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	8138 independent reflections
Radiation source: fine-focus sealed tube	4819 reflections with I > 2σ(I)
graphite	Rint = 0.039
ω scans	θmax = 30.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.440, Tmax = 0.561	k = −24→24
34672 measured reflections	l = −22→22

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0558P)2 + 1.4803P] where P = (Fo2 + 2Fc2)/3
8138 reflections	(Δ/σ)max = 0.002
355 parameters	Δρmax = 0.79 e Å−3
20 restraints	Δρmin = −0.76 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)
C5	0.0820 (3)	0.13111 (17)	0.74030 (19)	0.0400 (7)
H5A	0.0917	0.0934	0.6965	0.048*
H5B	−0.0043	0.1585	0.7257	0.048*
C6	0.2004 (3)	0.18591 (16)	0.74214 (17)	0.0335 (6)
C7	0.3347 (3)	0.16883 (16)	0.73313 (17)	0.0357 (6)
C8	0.4160 (3)	0.23518 (17)	0.74534 (18)	0.0359 (6)
C9	0.3326 (3)	0.29465 (16)	0.76079 (17)	0.0337 (6)
C10	0.3748 (3)	0.37604 (17)	0.77607 (18)	0.0372 (6)
H10A	0.2975	0.4082	0.7546	0.045*
H10B	0.4514	0.3869	0.7426	0.045*
C15	0.0367 (3)	0.33865 (18)	0.6355 (2)	0.0452 (7)
C16	0.1028 (4)	0.4005 (2)	0.6062 (2)	0.0591 (9)
H16	0.1580	0.4316	0.6432	0.071*
C17	0.0868 (5)	0.4165 (3)	0.5209 (3)	0.0812 (13)
H17	0.1331	0.4580	0.5000	0.097*
C18	0.0039 (7)	0.3722 (3)	0.4671 (3)	0.0974 (18)
H18	−0.0063	0.3835	0.4097	0.117*
C19	−0.0652 (7)	0.3108 (3)	0.4970 (3)	0.106 (2)
H19	−0.1228	0.2811	0.4599	0.127*
C20	−0.0490 (5)	0.2931 (2)	0.5821 (3)	0.0767 (13)
H20	−0.0948	0.2515	0.6029	0.092*
N1	0.1966 (2)	0.26458 (13)	0.76122 (15)	0.0329 (5)
O1	−0.0609 (2)	0.27254 (14)	0.76316 (18)	0.0588 (6)
O2	0.0806 (2)	0.38764 (13)	0.78932 (14)	0.0492 (5)
O3	0.2002 (3)	0.04497 (19)	0.8743 (2)	0.0855 (9)
O6	0.4468 (3)	0.48635 (13)	0.89029 (15)	0.0642 (7)
P1	0.07187 (10)	0.08262 (5)	0.83967 (6)	0.0522 (2)
P2	0.42646 (9)	0.40435 (5)	0.88263 (5)	0.0430 (2)
S1	0.05156 (8)	0.31902 (4)	0.74386 (5)	0.03984 (18)
Br1	0.40069 (4)	0.071636 (19)	0.71196 (2)	0.05379 (12)
Br2	0.60841 (3)	0.23995 (2)	0.74283 (3)	0.05732 (12)
O5	−0.0926 (10)	0.0770 (13)	0.8306 (16)	0.0668 (9)	0.121 (5)
C1	−0.248 (5)	−0.029 (3)	0.741 (3)	0.124 (3)	0.121 (5)
H1A	−0.3481	−0.0284	0.7344	0.186*	0.121 (5)
H1B	−0.2161	−0.0809	0.7469	0.186*	0.121 (5)
H1C	−0.2134	−0.0066	0.6921	0.186*	0.121 (5)
C2	−0.195 (5)	0.017 (3)	0.820 (4)	0.098 (2)	0.121 (5)
H2A	−0.2785	0.0386	0.8403	0.117*	0.121 (5)
H2B	−0.1631	−0.0216	0.8616	0.117*	0.121 (5)
O5'	−0.0402 (3)	0.01914 (17)	0.8237 (2)	0.0668 (9)	0.879 (5)
C1'	−0.2651 (6)	−0.0326 (4)	0.8086 (7)	0.124 (3)	0.879 (5)
H1'1	−0.2206	−0.0769	0.7880	0.186*	0.879 (5)
H1'2	−0.3563	−0.0272	0.7794	0.186*	0.879 (5)
H1'3	−0.2727	−0.0381	0.8681	0.186*	0.879 (5)
C2'	−0.1804 (6)	0.0369 (4)	0.7937 (5)	0.098 (2)	0.879 (5)
H2'1	−0.1871	0.0491	0.7339	0.117*	0.879 (5)
H2'2	−0.2131	0.0803	0.8240	0.117*	0.879 (5)
O4	0.009 (5)	0.1382 (13)	0.9016 (12)	0.078 (4)	0.411 (10)
C4	−0.007 (3)	0.1903 (13)	1.0324 (17)	0.173 (7)	0.411 (10)
H4A	0.0866	0.2090	1.0441	0.260*	0.411 (10)
H4B	−0.0482	0.1842	1.0845	0.260*	0.411 (10)
H4C	−0.0603	0.2260	0.9970	0.260*	0.411 (10)
C3	−0.004 (2)	0.1141 (11)	0.9879 (11)	0.125 (4)	0.411 (10)
H3A	0.0749	0.0835	1.0101	0.150*	0.411 (10)
H3B	−0.0892	0.0857	0.9923	0.150*	0.411 (10)
O4'	0.028 (3)	0.1505 (8)	0.8938 (8)	0.078 (4)	0.589 (10)
C3'	0.0613 (13)	0.1538 (9)	0.9850 (7)	0.125 (4)	0.589 (10)
H3'1	0.1069	0.2019	0.9999	0.150*	0.589 (10)
H3'2	0.1257	0.1130	1.0025	0.150*	0.589 (10)
C4'	−0.0661 (17)	0.1464 (14)	1.0318 (11)	0.173 (7)	0.589 (10)
H4'1	−0.1202	0.1035	1.0101	0.260*	0.589 (10)
H4'2	−0.1208	0.1921	1.0242	0.260*	0.589 (10)
H4'3	−0.0386	0.1389	1.0908	0.260*	0.589 (10)
O8	0.318 (2)	0.3710 (6)	0.9390 (13)	0.0637 (10)	0.719 (8)
C13	0.2084 (9)	0.4151 (5)	0.9727 (4)	0.078 (2)	0.719 (8)
H13A	0.1178	0.3962	0.9503	0.094*	0.719 (8)
H13B	0.2155	0.4684	0.9569	0.094*	0.719 (8)
C14	0.2251 (11)	0.4074 (6)	1.0654 (4)	0.115 (3)	0.719 (8)
H14A	0.2137	0.3548	1.0804	0.173*	0.719 (8)
H14B	0.1561	0.4378	1.0894	0.173*	0.719 (8)
H14C	0.3162	0.4244	1.0868	0.173*	0.719 (8)
O8'	0.322 (6)	0.3676 (15)	0.940 (3)	0.0637 (10)	0.281 (8)
C13'	0.278 (2)	0.4208 (13)	1.0017 (14)	0.078 (2)	0.281 (8)
H13C	0.2589	0.4709	0.9772	0.094*	0.281 (8)
H13D	0.3467	0.4254	1.0499	0.094*	0.281 (8)
C14'	0.145 (2)	0.3836 (16)	1.0264 (14)	0.115 (3)	0.281 (8)
H14D	0.0802	0.4224	1.0392	0.173*	0.281 (8)
H14E	0.1668	0.3519	1.0752	0.173*	0.281 (8)
H14F	0.1048	0.3529	0.9803	0.173*	0.281 (8)
O7	0.5503 (12)	0.3488 (9)	0.9077 (17)	0.054 (3)	0.609 (13)
C12	0.7959 (11)	0.3707 (10)	0.9575 (9)	0.120 (4)	0.609 (13)
H12A	0.8302	0.3249	0.9335	0.180*	0.609 (13)
H12B	0.8557	0.3845	1.0069	0.180*	0.609 (13)
H12C	0.7943	0.4112	0.9168	0.180*	0.609 (13)
C11	0.6496 (16)	0.3569 (8)	0.9817 (15)	0.079 (3)	0.609 (13)
H11A	0.6488	0.3110	1.0158	0.095*	0.609 (13)
H11B	0.6221	0.3994	1.0156	0.095*	0.609 (13)
O7'	0.569 (2)	0.3624 (16)	0.900 (3)	0.054 (3)	0.391 (13)
C11'	0.648 (3)	0.3788 (13)	0.980 (2)	0.079 (3)	0.391 (13)
H11C	0.5906	0.3750	1.0269	0.095*	0.391 (13)
H11D	0.6889	0.4295	0.9803	0.095*	0.391 (13)
C12'	0.7607 (19)	0.3174 (15)	0.9864 (14)	0.120 (4)	0.391 (13)
H12D	0.7218	0.2700	1.0031	0.180*	0.391 (13)
H12E	0.8352	0.3323	1.0275	0.180*	0.391 (13)
H12F	0.7959	0.3114	0.9323	0.180*	0.391 (13)

	U11	U22	U33	U12	U13	U23
C5	0.0387 (16)	0.0307 (15)	0.0499 (17)	−0.0039 (12)	−0.0003 (13)	−0.0013 (13)
C6	0.0332 (14)	0.0281 (14)	0.0393 (15)	0.0000 (11)	0.0035 (11)	−0.0014 (11)
C7	0.0373 (15)	0.0300 (14)	0.0400 (15)	0.0027 (12)	0.0052 (12)	−0.0054 (12)
C8	0.0257 (13)	0.0400 (16)	0.0430 (15)	−0.0003 (12)	0.0082 (11)	−0.0025 (13)
C9	0.0332 (14)	0.0296 (14)	0.0384 (15)	−0.0031 (12)	0.0031 (11)	−0.0008 (11)
C10	0.0357 (15)	0.0328 (15)	0.0423 (16)	−0.0052 (12)	−0.0002 (12)	0.0007 (12)
C15	0.0425 (17)	0.0370 (17)	0.0534 (18)	0.0123 (14)	−0.0096 (14)	−0.0056 (14)
C16	0.059 (2)	0.061 (2)	0.055 (2)	−0.0022 (19)	−0.0081 (17)	0.0075 (18)
C17	0.090 (3)	0.087 (3)	0.063 (3)	0.004 (3)	−0.006 (2)	0.017 (2)
C18	0.151 (5)	0.077 (3)	0.057 (3)	0.033 (4)	−0.025 (3)	−0.001 (2)
C19	0.158 (6)	0.071 (3)	0.075 (3)	0.020 (3)	−0.058 (3)	−0.020 (3)
C20	0.094 (3)	0.042 (2)	0.086 (3)	−0.001 (2)	−0.029 (2)	−0.006 (2)
N1	0.0310 (11)	0.0248 (11)	0.0426 (13)	0.0023 (9)	0.0013 (10)	−0.0015 (10)
O1	0.0335 (11)	0.0501 (14)	0.0946 (19)	0.0041 (10)	0.0150 (12)	0.0046 (13)
O2	0.0519 (13)	0.0376 (12)	0.0579 (14)	0.0112 (10)	0.0040 (11)	−0.0096 (10)
O3	0.079 (2)	0.086 (2)	0.091 (2)	0.0235 (17)	0.0097 (17)	0.0353 (18)
O6	0.098 (2)	0.0348 (13)	0.0568 (14)	−0.0080 (13)	−0.0081 (14)	−0.0076 (11)
P1	0.0545 (5)	0.0449 (5)	0.0587 (5)	−0.0079 (4)	0.0124 (4)	0.0034 (4)
P2	0.0529 (5)	0.0307 (4)	0.0442 (4)	−0.0004 (4)	−0.0008 (4)	−0.0029 (3)
S1	0.0312 (4)	0.0324 (4)	0.0559 (4)	0.0053 (3)	0.0039 (3)	−0.0020 (3)
Br1	0.0543 (2)	0.03644 (18)	0.0716 (2)	0.01011 (15)	0.01144 (17)	−0.01260 (15)
Br2	0.03251 (17)	0.0609 (2)	0.0805 (3)	−0.00089 (15)	0.01528 (16)	−0.01378 (18)
O5	0.0502 (17)	0.0469 (18)	0.105 (2)	−0.0058 (13)	0.0133 (16)	0.0164 (16)
C1	0.058 (3)	0.078 (4)	0.233 (10)	−0.026 (3)	−0.005 (5)	0.030 (6)
C2	0.052 (3)	0.081 (4)	0.158 (7)	0.003 (3)	0.001 (4)	0.042 (4)
O5'	0.0502 (17)	0.0469 (18)	0.105 (2)	−0.0058 (13)	0.0133 (16)	0.0164 (16)
C1'	0.058 (3)	0.078 (4)	0.233 (10)	−0.026 (3)	−0.005 (5)	0.030 (6)
C2'	0.052 (3)	0.081 (4)	0.158 (7)	0.003 (3)	0.001 (4)	0.042 (4)
O4	0.118 (8)	0.067 (5)	0.053 (3)	0.015 (6)	0.031 (3)	0.006 (3)
C4	0.176 (17)	0.26 (2)	0.088 (5)	−0.056 (11)	0.057 (9)	−0.045 (12)
C3	0.134 (11)	0.149 (13)	0.093 (5)	−0.023 (7)	0.014 (7)	−0.046 (7)
O4'	0.118 (8)	0.067 (5)	0.053 (3)	0.015 (6)	0.031 (3)	0.006 (3)
C3'	0.134 (11)	0.149 (13)	0.093 (5)	−0.023 (7)	0.014 (7)	−0.046 (7)
C4'	0.176 (17)	0.26 (2)	0.088 (5)	−0.056 (11)	0.057 (9)	−0.045 (12)
O8	0.083 (2)	0.0512 (18)	0.0605 (15)	0.0023 (17)	0.0247 (16)	0.0014 (15)
C13	0.075 (5)	0.096 (4)	0.066 (4)	0.012 (5)	0.020 (3)	−0.005 (4)
C14	0.125 (8)	0.159 (8)	0.065 (5)	0.005 (6)	0.026 (4)	0.001 (5)
O8'	0.083 (2)	0.0512 (18)	0.0605 (15)	0.0023 (17)	0.0247 (16)	0.0014 (15)
C13'	0.075 (5)	0.096 (4)	0.066 (4)	0.012 (5)	0.020 (3)	−0.005 (4)
C14'	0.125 (8)	0.159 (8)	0.065 (5)	0.005 (6)	0.026 (4)	0.001 (5)
O7	0.053 (3)	0.047 (6)	0.057 (4)	0.001 (4)	−0.015 (4)	−0.008 (4)
C12	0.067 (6)	0.157 (13)	0.130 (9)	0.014 (7)	−0.024 (5)	−0.033 (9)
C11	0.089 (4)	0.058 (8)	0.084 (3)	0.011 (5)	−0.028 (3)	−0.021 (7)
O7'	0.053 (3)	0.047 (6)	0.057 (4)	0.001 (4)	−0.015 (4)	−0.008 (4)
C11'	0.089 (4)	0.058 (8)	0.084 (3)	0.011 (5)	−0.028 (3)	−0.021 (7)
C12'	0.067 (6)	0.157 (13)	0.130 (9)	0.014 (7)	−0.024 (5)	−0.033 (9)

C5—C6	1.491 (4)	C1'—C2'	1.497 (6)
C5—P1	1.804 (3)	C1'—H1'1	0.9600
C5—H5A	0.9700	C1'—H1'2	0.9600
C5—H5B	0.9700	C1'—H1'3	0.9600
C6—C7	1.351 (4)	C2'—H2'1	0.9700
C6—N1	1.412 (3)	C2'—H2'2	0.9700
C7—C8	1.405 (4)	O4—C3	1.453 (10)
C7—Br1	1.860 (3)	C4—C3	1.511 (10)
C8—C9	1.353 (4)	C4—H4A	0.9600
C8—Br2	1.863 (3)	C4—H4B	0.9600
C9—N1	1.415 (4)	C4—H4C	0.9600
C9—C10	1.496 (4)	C3—H3A	0.9700
C10—P2	1.789 (3)	C3—H3B	0.9700
C10—H10A	0.9700	O4'—C3'	1.456 (10)
C10—H10B	0.9700	C3'—C4'	1.502 (9)
C15—C16	1.363 (5)	C3'—H3'1	0.9700
C15—C20	1.381 (5)	C3'—H3'2	0.9700
C15—S1	1.748 (3)	C4'—H4'1	0.9600
C16—C17	1.379 (6)	C4'—H4'2	0.9600
C16—H16	0.9300	C4'—H4'3	0.9600
C17—C18	1.357 (7)	O8—C13	1.451 (10)
C17—H17	0.9300	C13—C14	1.473 (7)
C18—C19	1.374 (8)	C13—H13A	0.9700
C18—H18	0.9300	C13—H13B	0.9700
C19—C20	1.382 (7)	C14—H14A	0.9600
C19—H19	0.9300	C14—H14B	0.9600
C20—H20	0.9300	C14—H14C	0.9600
N1—S1	1.694 (2)	O8'—C13'	1.450 (10)
O1—S1	1.414 (3)	C13'—C14'	1.519 (10)
O2—S1	1.416 (2)	C13'—H13C	0.9700
O3—P1	1.463 (3)	C13'—H13D	0.9700
O6—P2	1.453 (2)	C14'—H14D	0.9600
P1—O4	1.548 (7)	C14'—H14E	0.9600
P1—O4'	1.549 (6)	C14'—H14F	0.9600
P1—O5'	1.555 (3)	O7—C11	1.452 (7)
P1—O5	1.583 (10)	C12—C11	1.518 (10)
P2—O8'	1.558 (8)	C12—H12A	0.9600
P2—O8	1.558 (4)	C12—H12B	0.9600
P2—O7'	1.561 (7)	C12—H12C	0.9600
P2—O7	1.563 (5)	C11—H11A	0.9700
O5—C2	1.447 (10)	C11—H11B	0.9700
O5—O4	1.78 (4)	O7'—C11'	1.448 (9)
C1—C2	1.539 (10)	C11'—C12'	1.524 (10)
C1—H1A	0.9600	C11'—H11C	0.9700
C1—H1B	0.9600	C11'—H11D	0.9700
C1—H1C	0.9600	C12'—H12D	0.9600
C2—H2A	0.9700	C12'—H12E	0.9600
C2—H2B	0.9700	C12'—H12F	0.9600
O5'—C2'	1.425 (6)
C6—C5—P1	113.1 (2)	O5—C2—H2A	104.8
C6—C5—H5A	109.0	C1—C2—H2A	104.8
P1—C5—H5A	109.0	O5—C2—H2B	104.8
C6—C5—H5B	109.0	C1—C2—H2B	104.8
P1—C5—H5B	109.0	H2A—C2—H2B	105.8
H5A—C5—H5B	107.8	C2'—O5'—P1	121.5 (3)
C7—C6—N1	106.5 (2)	C2'—C1'—H1'1	109.5
C7—C6—C5	126.7 (3)	C2'—C1'—H1'2	109.5
N1—C6—C5	126.6 (2)	H1'1—C1'—H1'2	109.5
C6—C7—C8	109.3 (2)	C2'—C1'—H1'3	109.5
C6—C7—Br1	124.8 (2)	H1'1—C1'—H1'3	109.5
C8—C7—Br1	125.8 (2)	H1'2—C1'—H1'3	109.5
C9—C8—C7	109.1 (2)	O5'—C2'—C1'	106.6 (5)
C9—C8—Br2	125.5 (2)	O5'—C2'—H2'1	110.4
C7—C8—Br2	125.4 (2)	C1'—C2'—H2'1	110.4
C8—C9—N1	106.4 (2)	O5'—C2'—H2'2	110.4
C8—C9—C10	127.3 (3)	C1'—C2'—H2'2	110.4
N1—C9—C10	126.3 (3)	H2'1—C2'—H2'2	108.6
C9—C10—P2	117.7 (2)	C3—O4—P1	119.6 (13)
C9—C10—H10A	107.9	C3—O4—O5	109 (2)
P2—C10—H10A	107.9	P1—O4—O5	56.3 (10)
C9—C10—H10B	107.9	O4—C3—C4	101.2 (16)
P2—C10—H10B	107.9	O4—C3—H3A	111.5
H10A—C10—H10B	107.2	C4—C3—H3A	111.5
C16—C15—C20	121.4 (4)	O4—C3—H3B	111.5
C16—C15—S1	119.8 (3)	C4—C3—H3B	111.5
C20—C15—S1	118.7 (3)	H3A—C3—H3B	109.3
C15—C16—C17	119.1 (4)	C3'—O4'—P1	122.6 (11)
C15—C16—H16	120.5	O4'—C3'—C4'	112.3 (14)
C17—C16—H16	120.5	O4'—C3'—H3'1	109.1
C18—C17—C16	120.4 (5)	C4'—C3'—H3'1	109.1
C18—C17—H17	119.8	O4'—C3'—H3'2	109.1
C16—C17—H17	119.8	C4'—C3'—H3'2	109.1
C17—C18—C19	120.4 (4)	H3'1—C3'—H3'2	107.9
C17—C18—H18	119.8	C3'—C4'—H4'1	109.5
C19—C18—H18	119.8	C3'—C4'—H4'2	109.5
C18—C19—C20	120.0 (4)	H4'1—C4'—H4'2	109.5
C18—C19—H19	120.0	C3'—C4'—H4'3	109.5
C20—C19—H19	120.0	H4'1—C4'—H4'3	109.5
C15—C20—C19	118.5 (5)	H4'2—C4'—H4'3	109.5
C15—C20—H20	120.7	C13—O8—P2	124.5 (9)
C19—C20—H20	120.7	O8—C13—C14	107.8 (11)
C6—N1—C9	108.6 (2)	O8—C13—H13A	110.1
C6—N1—S1	123.55 (19)	C14—C13—H13A	110.1
C9—N1—S1	122.83 (19)	O8—C13—H13B	110.1
O3—P1—O4	114.4 (13)	C14—C13—H13B	110.1
O3—P1—O4'	113.7 (10)	H13A—C13—H13B	108.5
O3—P1—O5'	106.83 (19)	C13'—O8'—P2	112.4 (14)
O4—P1—O5'	104.2 (17)	O8'—C13'—C14'	102.2 (17)
O4'—P1—O5'	114.7 (11)	O8'—C13'—H13C	111.3
O3—P1—O5	144.2 (8)	C14'—C13'—H13C	111.3
O4—P1—O5	69 (2)	O8'—C13'—H13D	111.3
O4'—P1—O5	77.1 (15)	C14'—C13'—H13D	111.3
O3—P1—C5	115.23 (17)	H13C—C13'—H13D	109.2
O4—P1—C5	108.5 (8)	C13'—C14'—H14D	109.5
O4'—P1—C5	99.5 (5)	C13'—C14'—H14E	109.5
O5'—P1—C5	106.80 (16)	H14D—C14'—H14E	109.5
O5—P1—C5	95.0 (9)	C13'—C14'—H14F	109.5
O6—P2—O8'	116.7 (9)	H14D—C14'—H14F	109.5
O6—P2—O8	114.5 (4)	H14E—C14'—H14F	109.5
O6—P2—O7'	109.9 (13)	C11—O7—P2	125.1 (15)
O8'—P2—O7'	108 (3)	O7—C11—C12	111.6 (13)
O8—P2—O7'	110.5 (17)	O7—C11—H11A	109.3
O6—P2—O7	120.0 (7)	C12—C11—H11A	109.3
O8'—P2—O7	97 (2)	O7—C11—H11B	109.3
O8—P2—O7	99.3 (12)	C12—C11—H11B	109.3
O6—P2—C10	112.10 (15)	H11A—C11—H11B	108.0
O8'—P2—C10	107 (2)	C11'—O7'—P2	117 (2)
O8—P2—C10	107.4 (9)	O7'—C11'—C12'	103.2 (16)
O7'—P2—C10	101.7 (16)	O7'—C11'—H11C	111.1
O7—P2—C10	101.9 (10)	C12'—C11'—H11C	111.1
O1—S1—O2	119.75 (15)	O7'—C11'—H11D	111.1
O1—S1—N1	106.26 (13)	C12'—C11'—H11D	111.1
O2—S1—N1	105.94 (13)	H11C—C11'—H11D	109.1
O1—S1—C15	109.56 (16)	C11'—C12'—H12D	109.5
O2—S1—C15	109.22 (15)	C11'—C12'—H12E	109.5
N1—S1—C15	105.04 (13)	H12D—C12'—H12E	109.5
C2—O5—P1	137 (3)	C11'—C12'—H12F	109.5
C2—O5—O4	147 (3)	H12D—C12'—H12F	109.5
P1—O5—O4	54.4 (11)	H12E—C12'—H12F	109.5
O5—C2—C1	130 (4)
P1—C5—C6—C7	81.3 (3)	C5—P1—O5—C2	114 (4)
P1—C5—C6—N1	−92.5 (3)	O3—P1—O5—O4	103.4 (16)
N1—C6—C7—C8	−0.5 (3)	O4'—P1—O5—O4	−9.3 (14)
C5—C6—C7—C8	−175.4 (3)	O5'—P1—O5—O4	142.6 (16)
N1—C6—C7—Br1	177.33 (19)	C5—P1—O5—O4	−107.9 (10)
C5—C6—C7—Br1	2.5 (4)	P1—O5—C2—C1	−78 (7)
C6—C7—C8—C9	−1.0 (3)	O4—O5—C2—C1	−172 (4)
Br1—C7—C8—C9	−178.8 (2)	O3—P1—O5'—C2'	176.9 (5)
C6—C7—C8—Br2	177.9 (2)	O4—P1—O5'—C2'	55.5 (11)
Br1—C7—C8—Br2	0.0 (4)	O4'—P1—O5'—C2'	50.0 (8)
C7—C8—C9—N1	2.0 (3)	O5—P1—O5'—C2'	19.6 (14)
Br2—C8—C9—N1	−176.8 (2)	C5—P1—O5'—C2'	−59.3 (5)
C7—C8—C9—C10	−179.0 (3)	P1—O5'—C2'—C1'	−164.6 (5)
Br2—C8—C9—C10	2.2 (4)	O3—P1—O4—C3	−47 (4)
C8—C9—C10—P2	−89.0 (3)	O4'—P1—O4—C3	−136 (13)
N1—C9—C10—P2	89.8 (3)	O5'—P1—O4—C3	69 (3)
C20—C15—C16—C17	−1.9 (6)	O5—P1—O4—C3	95 (3)
S1—C15—C16—C17	−178.1 (3)	C5—P1—O4—C3	−177 (3)
C15—C16—C17—C18	1.4 (7)	O3—P1—O4—O5	−141.4 (10)
C16—C17—C18—C19	0.0 (8)	O4'—P1—O4—O5	130 (11)
C17—C18—C19—C20	−0.9 (9)	O5'—P1—O4—O5	−25.1 (10)
C16—C15—C20—C19	1.0 (6)	C5—P1—O4—O5	88.4 (11)
S1—C15—C20—C19	177.3 (4)	C2—O5—O4—C3	9(6)
C18—C19—C20—C15	0.4 (8)	P1—O5—O4—C3	−113.2 (18)
C7—C6—N1—C9	1.8 (3)	C2—O5—O4—P1	123 (6)
C5—C6—N1—C9	176.6 (3)	P1—O4—C3—C4	156 (3)
C7—C6—N1—S1	157.1 (2)	O5—O4—C3—C4	−142.1 (19)
C5—C6—N1—S1	−28.1 (4)	O3—P1—O4'—C3'	−30 (2)
C8—C9—N1—C6	−2.4 (3)	O4—P1—O4'—C3'	66 (9)
C10—C9—N1—C6	178.6 (3)	O5'—P1—O4'—C3'	93 (2)
C8—C9—N1—S1	−157.9 (2)	O5—P1—O4'—C3'	114 (2)
C10—C9—N1—S1	23.1 (4)	C5—P1—O4'—C3'	−153 (2)
C6—C5—P1—O3	−52.7 (3)	P1—O4'—C3'—C4'	−111 (2)
C6—C5—P1—O4	77.1 (18)	O6—P2—O8—C13	22 (2)
C6—C5—P1—O4'	69.2 (12)	O8'—P2—O8—C13	165 (65)
C6—C5—P1—O5'	−171.2 (2)	O7'—P2—O8—C13	147 (2)
C6—C5—P1—O5	146.9 (9)	O7—P2—O8—C13	151 (2)
C9—C10—P2—O6	−172.3 (2)	C10—P2—O8—C13	−103.3 (18)
C9—C10—P2—O8'	−42.9 (19)	P2—O8—C13—C14	−122.5 (19)
C9—C10—P2—O8	−45.7 (8)	O6—P2—O8'—C13'	−9(6)
C9—C10—P2—O7'	70.4 (13)	O8—P2—O8'—C13'	−47 (58)
C9—C10—P2—O7	58.1 (8)	O7'—P2—O8'—C13'	115 (4)
C6—N1—S1—O1	37.7 (3)	O7—P2—O8'—C13'	119 (4)
C9—N1—S1—O1	−170.4 (2)	C10—P2—O8'—C13'	−136 (4)
C6—N1—S1—O2	166.1 (2)	P2—O8'—C13'—C14'	161 (4)
C9—N1—S1—O2	−42.0 (3)	O6—P2—O7—C11	42 (2)
C6—N1—S1—C15	−78.4 (3)	O8'—P2—O7—C11	−84 (2)
C9—N1—S1—C15	73.5 (2)	O8—P2—O7—C11	−83.4 (18)
C16—C15—S1—O1	158.4 (3)	O7'—P2—O7—C11	76 (12)
C20—C15—S1—O1	−17.9 (3)	C10—P2—O7—C11	166.5 (16)
C16—C15—S1—O2	25.5 (3)	P2—O7—C11—C12	−116 (2)
C20—C15—S1—O2	−150.8 (3)	O6—P2—O7'—C11'	55 (3)
C16—C15—S1—N1	−87.8 (3)	O8'—P2—O7'—C11'	−73 (3)
C20—C15—S1—N1	95.9 (3)	O8—P2—O7'—C11'	−72 (3)
O3—P1—O5—C2	−35 (5)	O7—P2—O7'—C11'	−94 (13)
O4—P1—O5—C2	−138 (4)	C10—P2—O7'—C11'	174 (2)
O4'—P1—O5—C2	−148 (4)	P2—O7'—C11'—C12'	168 (3)
O5'—P1—O5—C2	4(4)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O6i	0.97	2.34	3.272 (4)	162
C16—H16···O3ii	0.93	2.44	3.162 (5)	134
C11—H11B···O6iii	0.97	2.62	3.592 (19)	179.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O6i	0.97	2.34	3.272 (4)	162
C16—H16⋯O3ii	0.93	2.44	3.162 (5)	134
C11—H11B⋯O6iii	0.97	2.62	3.592 (19)	179

Symmetry codes: (i) ; (ii) ; (iii) .