3'-O-Acetyl-2'-de-oxy-uridine.

In the two independent but very similar mol-ecules of the title compound, C(11)H(14)N(2)O(6), both nucleobase fragments are nearly planar (both within 0.01 Å) while the furan-ose rings exhibit (2)E-endo envelope conformations. In the crystal, the two 3'-O-acetyl-2'-de-oxy-uridine mol-ecules form a pseudosymmetric dimer of two bases connected via two nearly identical resonance-assisted N-H⋯O hydrogen bonds. The resulting pair is further connected with neighboring pairs via two similar O-H⋯O bonds involving the only hydroxyl group of the 2'-de-oxy-furan-ose fragment and the remaining carbonyl oxygen of the nucleobase. These inter-actions result in the formation of an infinite 'double band' along the b axis that can be considered as a self-assembled analogue of a polynucleotide mol-ecule with non-canonical Watson-Crick base pairs. The infinite chains of 3'-O-acetyl-2'-de-oxy-uridine pairs are additionally held together by C-H⋯O inter-actions involving C atoms of the uracyl base and O atoms of carbonyl groups. Only weak C-H⋯O contacts exist between neighboring chains.

Related literature

For syntheses of this and similar compounds, see: Smrt & Sorm (1960 ▶); Cabral et al. (2008 ▶). For related structures of uridines, see: de Graaff et al. (1977 ▶); Green et al. (1975 ▶); Low & Wilson (1984 ▶); Luo et al. (2007 ▶); Marck et al. (1982 ▶); Rahman & Wilson (1972 ▶); Suck et al. (1972 ▶). For conformations of five-membered rings, see: Schwarz (1973 ▶); Cremer & Pople (1975 ▶); Boeyens & Dobson (1987 ▶). For analysis of absolute structure, see: Flack (1983 ▶), Hooft et al. (2008 ▶). For hydrogen bonding in nucleotide chemistry, see: Gilli & Gilli (2009 ▶); Desiraju & Steiner (1999 ▶); Jeffrey (1997 ▶); Nagaswamy et al.(2000 ▶) and references therein. For similar UU-4-carbon­yl–imino pairs in RNA structures, see: Ban et al. (2000 ▶); Jiang & Patel (1998 ▶).

Experimental

Crystal data

C11H14N2O6

M = 270.24

Monoclinic,

a = 22.8919 (4) Å

b = 6.8676 (1) Å

c = 17.2789 (12) Å

β = 111.307 (8)°

V = 2530.8 (2) Å3

Z = 8

Cu Kα radiation

μ = 1.00 mm−1

T = 291 K

0.2 × 0.15 × 0.1 mm

Data collection

Rigaku R-AXIS RAPID II imaging plate diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.84, T max = 0.88

11957 measured reflections

4372 independent reflections

2609 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.149

S = 1.10

4372 reflections

346 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 1927 Friedel pairs

Flack parameter: 0.0 (2)

Data collection: CrystalClear-SM Expert (Rigaku, 2009 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681004938X/zl2331sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004938X/zl2331Isup2.hkl

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

Enhanced figure: interactive version of Fig. 7

C11H14N2O6	F(000) = 1136
Mr = 270.24	Dx = 1.418 Mg m−3
Monoclinic, C2	Melting point: 461 K
Hall symbol: C 2y	Cu Kα radiation, λ = 1.54187 Å
a = 22.8919 (4) Å	Cell parameters from 9690 reflections
b = 6.8676 (1) Å	θ = 6.8–68.2°
c = 17.2789 (12) Å	µ = 1.00 mm−1
β = 111.307 (8)°	T = 291 K
V = 2530.8 (2) Å3	Block, colourless
Z = 8	0.2 × 0.15 × 0.1 mm

Rigaku R-AXIS RAPID II imaging plate diffractometer	4372 independent reflections
Radiation source: fine-focus sealed tube	2609 reflections with I > 2σ(I)
graphite	Rint = 0.069
Detector resolution: 10 pixels mm-1	θmax = 67.0°, θmin = 6.8°
ω scans	h = −27→22
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −8→7
Tmin = 0.84, Tmax = 0.88	l = −17→20
11957 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.048	w = 1/[σ2(Fo2) + (0.0552P)2 + 0.1596P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.149	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.24 e Å−3
4372 reflections	Δρmin = −0.24 e Å−3
346 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.0016 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1927 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.0 (2)

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
O1	0.46379 (15)	0.4346 (4)	0.81776 (18)	0.0769 (9)
O2	0.40640 (14)	0.0919 (4)	1.00331 (19)	0.0794 (9)
O3	0.46084 (12)	−0.0505 (4)	0.68957 (16)	0.0697 (8)
O4	0.54767 (15)	−0.3837 (5)	0.7567 (2)	0.0912 (11)
H1	0.5257	−0.4439	0.7769	0.137*
O5	0.56917 (13)	0.1405 (4)	0.63582 (18)	0.0689 (8)
O6	0.59476 (16)	−0.0887 (6)	0.5611 (2)	0.0920 (11)
N1	0.46541 (16)	0.1042 (5)	0.8110 (2)	0.0590 (9)
N2	0.43469 (16)	0.2568 (5)	0.9092 (2)	0.0631 (9)
H2	0.4267	0.3631	0.9297	0.076*
C1	0.45611 (19)	0.2760 (6)	0.8447 (2)	0.0562 (10)
C2	0.4246 (2)	0.0868 (7)	0.9442 (3)	0.0698 (12)
C3	0.4369 (2)	−0.0844 (7)	0.9075 (3)	0.0809 (15)
H3A	0.4314	−0.2061	0.9274	0.097*
C4	0.4567 (2)	−0.0696 (7)	0.8439 (3)	0.0743 (13)
H4A	0.4649	−0.1836	0.8206	0.089*
C5	0.48799 (18)	0.1107 (6)	0.7418 (2)	0.0563 (10)
H5A	0.4743	0.2322	0.7107	0.068*
C6	0.55755 (18)	0.0894 (6)	0.7668 (2)	0.0612 (11)
H6A	0.5749	0.0100	0.8163	0.073*
H6B	0.5781	0.2153	0.7767	0.073*
C7	0.56437 (19)	−0.0114 (6)	0.6914 (2)	0.0609 (11)
H7A	0.6012	−0.0965	0.7082	0.073*
C8	0.5048 (2)	−0.1272 (6)	0.6545 (3)	0.0640 (11)
H8A	0.4877	−0.1063	0.5943	0.077*
C9	0.5126 (2)	−0.3445 (7)	0.6714 (3)	0.0788 (14)
H9A	0.4716	−0.4047	0.6559	0.095*
H9B	0.5339	−0.4016	0.6375	0.095*
C10	0.5876 (2)	0.0811 (9)	0.5732 (3)	0.0784 (14)
C11	0.5960 (3)	0.2490 (9)	0.5245 (3)	0.110 (2)
H11A	0.6366	0.2416	0.5201	0.164*
H11B	0.5928	0.3680	0.5518	0.164*
H11C	0.5641	0.2462	0.4699	0.164*
O21	0.70463 (14)	0.1998 (4)	0.87917 (18)	0.0703 (8)
O22	0.61778 (17)	0.5604 (4)	1.0291 (2)	0.1020 (13)
O23	0.78772 (13)	0.6734 (4)	0.82972 (16)	0.0676 (8)
O24	0.71663 (15)	1.0090 (5)	0.7407 (2)	0.0874 (10)
H24	0.7181	1.0662	0.7830	0.131*
O25	0.76788 (13)	0.4633 (5)	0.65709 (18)	0.0737 (9)
O26	0.80745 (19)	0.6677 (7)	0.5882 (2)	0.1077 (13)
N21	0.71512 (15)	0.5305 (5)	0.87739 (19)	0.0575 (9)
N22	0.66228 (16)	0.3867 (5)	0.9545 (2)	0.0647 (9)
H22	0.6502	0.2828	0.9722	0.078*
C21	0.6952 (2)	0.3601 (7)	0.9015 (3)	0.0588 (11)
C22	0.6469 (2)	0.5612 (7)	0.9816 (3)	0.0710 (13)
C23	0.6674 (2)	0.7311 (6)	0.9510 (2)	0.0638 (12)
H23A	0.6586	0.8544	0.9663	0.077*
C24	0.6993 (2)	0.7113 (5)	0.9002 (2)	0.0610 (11)
H24A	0.7114	0.8228	0.8794	0.073*
C25	0.74536 (19)	0.5179 (6)	0.8160 (2)	0.0582 (10)
H25A	0.7679	0.3940	0.8225	0.070*
C26	0.69949 (18)	0.5388 (7)	0.7270 (2)	0.0625 (11)
H26A	0.6828	0.4134	0.7034	0.075*
H26B	0.6651	0.6248	0.7238	0.075*
C27	0.73937 (19)	0.6245 (6)	0.6843 (2)	0.0614 (11)
H27A	0.7148	0.7069	0.6375	0.074*
C28	0.7886 (2)	0.7422 (6)	0.7511 (3)	0.0641 (11)
H28A	0.8298	0.7140	0.7485	0.077*
C29	0.7786 (2)	0.9609 (7)	0.7462 (3)	0.0813 (14)
H29A	0.8087	1.0218	0.7951	0.098*
H29B	0.7856	1.0113	0.6979	0.098*
C30	0.7987 (2)	0.5034 (9)	0.6061 (3)	0.0817 (15)
C31	0.8202 (2)	0.3226 (9)	0.5769 (3)	0.108 (2)
H31A	0.8428	0.3565	0.5417	0.162*
H31B	0.7846	0.2443	0.5463	0.162*
H31C	0.8472	0.2506	0.6240	0.162*

	U11	U22	U33	U12	U13	U23
O1	0.111 (2)	0.0498 (18)	0.092 (2)	−0.0016 (18)	0.0627 (19)	0.0023 (17)
O2	0.103 (2)	0.065 (2)	0.098 (2)	0.0078 (17)	0.070 (2)	0.0114 (17)
O3	0.0616 (17)	0.0763 (19)	0.0791 (19)	−0.0050 (16)	0.0350 (15)	−0.0208 (16)
O4	0.087 (2)	0.080 (2)	0.102 (2)	−0.0043 (18)	0.0301 (19)	0.0241 (19)
O5	0.080 (2)	0.0643 (19)	0.0775 (19)	0.0011 (16)	0.0471 (16)	0.0052 (16)
O6	0.108 (3)	0.099 (3)	0.087 (2)	−0.001 (2)	0.058 (2)	−0.018 (2)
N1	0.077 (2)	0.045 (2)	0.072 (2)	0.0068 (17)	0.0471 (19)	0.0022 (17)
N2	0.085 (2)	0.045 (2)	0.078 (2)	0.0013 (18)	0.052 (2)	0.0004 (18)
C1	0.064 (3)	0.048 (2)	0.069 (3)	0.000 (2)	0.039 (2)	0.000 (2)
C2	0.084 (3)	0.060 (3)	0.080 (3)	0.002 (2)	0.048 (3)	0.005 (3)
C3	0.119 (4)	0.049 (3)	0.106 (4)	0.007 (3)	0.078 (3)	0.005 (3)
C4	0.101 (4)	0.047 (3)	0.095 (3)	−0.006 (2)	0.059 (3)	0.001 (2)
C5	0.064 (3)	0.052 (2)	0.065 (2)	−0.004 (2)	0.038 (2)	−0.003 (2)
C6	0.061 (2)	0.065 (3)	0.068 (2)	−0.005 (2)	0.036 (2)	−0.007 (2)
C7	0.061 (3)	0.057 (3)	0.074 (3)	0.001 (2)	0.035 (2)	0.005 (2)
C8	0.078 (3)	0.058 (3)	0.059 (2)	−0.001 (2)	0.029 (2)	−0.005 (2)
C9	0.090 (3)	0.063 (3)	0.089 (3)	−0.006 (3)	0.040 (3)	−0.010 (3)
C10	0.077 (3)	0.097 (4)	0.073 (3)	−0.011 (3)	0.040 (3)	−0.016 (3)
C11	0.135 (5)	0.127 (5)	0.091 (4)	−0.033 (4)	0.069 (4)	0.012 (4)
O21	0.092 (2)	0.0456 (18)	0.086 (2)	0.0012 (16)	0.0480 (17)	−0.0062 (16)
O22	0.160 (3)	0.062 (2)	0.141 (3)	0.013 (2)	0.124 (3)	0.006 (2)
O23	0.0711 (18)	0.0721 (19)	0.0663 (17)	−0.0189 (15)	0.0328 (14)	−0.0018 (15)
O24	0.084 (2)	0.081 (3)	0.103 (3)	0.0105 (18)	0.0398 (18)	−0.015 (2)
O25	0.083 (2)	0.077 (2)	0.078 (2)	−0.0012 (18)	0.0493 (17)	−0.0081 (17)
O26	0.119 (3)	0.125 (3)	0.107 (3)	0.007 (3)	0.074 (2)	0.025 (3)
N21	0.067 (2)	0.052 (2)	0.063 (2)	0.0026 (16)	0.0364 (17)	0.0013 (17)
N22	0.084 (2)	0.050 (2)	0.082 (2)	0.0043 (18)	0.055 (2)	0.0060 (18)
C21	0.071 (3)	0.050 (3)	0.060 (2)	−0.005 (2)	0.030 (2)	0.001 (2)
C22	0.098 (4)	0.049 (3)	0.077 (3)	0.010 (2)	0.045 (3)	0.004 (2)
C23	0.087 (3)	0.046 (3)	0.072 (3)	0.007 (2)	0.045 (3)	−0.001 (2)
C24	0.083 (3)	0.040 (2)	0.069 (3)	0.002 (2)	0.038 (2)	0.005 (2)
C25	0.064 (2)	0.053 (3)	0.068 (3)	−0.001 (2)	0.038 (2)	0.003 (2)
C26	0.061 (3)	0.065 (3)	0.066 (3)	−0.006 (2)	0.029 (2)	−0.007 (2)
C27	0.064 (3)	0.062 (3)	0.064 (2)	0.004 (2)	0.031 (2)	−0.002 (2)
C28	0.066 (3)	0.064 (3)	0.076 (3)	−0.001 (2)	0.043 (2)	0.003 (2)
C29	0.093 (4)	0.071 (3)	0.093 (3)	−0.008 (3)	0.048 (3)	−0.006 (3)
C30	0.068 (3)	0.108 (5)	0.076 (3)	−0.004 (3)	0.034 (3)	−0.002 (3)
C31	0.092 (4)	0.141 (6)	0.113 (4)	−0.020 (4)	0.063 (3)	−0.052 (4)

O1—C1	1.223 (5)	O21—C21	1.212 (5)
O2—C2	1.236 (5)	O22—C22	1.230 (5)
O3—C5	1.421 (5)	O23—C25	1.404 (4)
O3—C8	1.449 (4)	O23—C28	1.445 (4)
O4—C9	1.425 (5)	O24—C29	1.425 (5)
O4—H1	0.8200	O24—H24	0.8200
O5—C10	1.358 (5)	O25—C30	1.342 (5)
O5—C7	1.449 (5)	O25—C27	1.447 (5)
O6—C10	1.207 (6)	O26—C30	1.206 (6)
N1—C4	1.367 (5)	N21—C21	1.375 (5)
N1—C1	1.366 (5)	N21—C24	1.390 (5)
N1—C5	1.467 (4)	N21—C25	1.464 (5)
N2—C2	1.373 (5)	N22—C22	1.379 (5)
N2—C1	1.376 (4)	N22—C21	1.392 (5)
N2—H2	0.8600	N22—H22	0.8600
C2—C3	1.412 (6)	C22—C23	1.429 (6)
C3—C4	1.336 (5)	C23—C24	1.337 (5)
C3—H3A	0.9300	C23—H23A	0.9300
C4—H4A	0.9300	C24—H24A	0.9300
C5—C6	1.498 (5)	C25—C26	1.522 (5)
C5—H5A	0.9800	C25—H25A	0.9800
C6—C7	1.532 (5)	C26—C27	1.488 (5)
C6—H6A	0.9700	C26—H26A	0.9700
C6—H6B	0.9700	C26—H26B	0.9700
C7—C8	1.506 (6)	C27—C28	1.520 (6)
C7—H7A	0.9800	C27—H27A	0.9800
C8—C9	1.519 (6)	C28—C29	1.517 (7)
C8—H8A	0.9800	C28—H28A	0.9800
C9—H9A	0.9700	C29—H29A	0.9700
C9—H9B	0.9700	C29—H29B	0.9700
C10—C11	1.482 (7)	C30—C31	1.489 (7)
C11—H11A	0.9600	C31—H31A	0.9600
C11—H11B	0.9600	C31—H31B	0.9600
C11—H11C	0.9600	C31—H31C	0.9600
C5—O3—C8	109.8 (3)	C25—O23—C28	109.6 (3)
C9—O4—H1	109.5	C29—O24—H24	109.5
C10—O5—C7	115.6 (4)	C30—O25—C27	117.6 (4)
C4—N1—C1	120.5 (3)	C21—N21—C24	121.7 (3)
C4—N1—C5	120.9 (4)	C21—N21—C25	117.7 (3)
C1—N1—C5	118.5 (3)	C24—N21—C25	119.9 (3)
C2—N2—C1	127.2 (4)	C22—N22—C21	127.1 (4)
C2—N2—H2	116.4	C22—N22—H22	116.4
C1—N2—H2	116.4	C21—N22—H22	116.4
O1—C1—N1	122.7 (4)	O21—C21—N21	124.0 (4)
O1—C1—N2	122.5 (4)	O21—C21—N22	122.0 (4)
N1—C1—N2	114.7 (4)	N21—C21—N22	114.0 (4)
O2—C2—N2	120.1 (4)	O22—C22—N22	119.3 (4)
O2—C2—C3	125.3 (4)	O22—C22—C23	125.5 (4)
N2—C2—C3	114.6 (4)	N22—C22—C23	115.2 (4)
C4—C3—C2	119.3 (4)	C24—C23—C22	119.4 (4)
C4—C3—H3A	120.4	C24—C23—H23A	120.3
C2—C3—H3A	120.4	C22—C23—H23A	120.3
C3—C4—N1	123.5 (4)	C23—C24—N21	122.5 (4)
C3—C4—H4A	118.2	C23—C24—H24A	118.7
N1—C4—H4A	118.2	N21—C24—H24A	118.7
O3—C5—N1	107.0 (3)	O23—C25—N21	108.2 (3)
O3—C5—C6	106.3 (3)	O23—C25—C26	106.2 (3)
N1—C5—C6	114.5 (3)	N21—C25—C26	113.1 (3)
O3—C5—H5A	109.6	O23—C25—H25A	109.7
N1—C5—H5A	109.6	N21—C25—H25A	109.7
C6—C5—H5A	109.6	C26—C25—H25A	109.7
C5—C6—C7	103.0 (3)	C27—C26—C25	102.5 (3)
C5—C6—H6A	111.2	C27—C26—H26A	111.3
C7—C6—H6A	111.2	C25—C26—H26A	111.3
C5—C6—H6B	111.2	C27—C26—H26B	111.3
C7—C6—H6B	111.2	C25—C26—H26B	111.3
H6A—C6—H6B	109.1	H26A—C26—H26B	109.2
O5—C7—C8	112.0 (3)	O25—C27—C26	106.8 (3)
O5—C7—C6	107.1 (3)	O25—C27—C28	110.8 (3)
C8—C7—C6	104.0 (3)	C26—C27—C28	104.6 (3)
O5—C7—H7A	111.2	O25—C27—H27A	111.4
C8—C7—H7A	111.2	C26—C27—H27A	111.4
C6—C7—H7A	111.2	C28—C27—H27A	111.4
O3—C8—C7	106.9 (3)	O23—C28—C29	108.8 (4)
O3—C8—C9	109.1 (4)	O23—C28—C27	106.3 (3)
C7—C8—C9	114.3 (4)	C29—C28—C27	115.4 (4)
O3—C8—H8A	108.8	O23—C28—H28A	108.7
C7—C8—H8A	108.8	C29—C28—H28A	108.7
C9—C8—H8A	108.8	C27—C28—H28A	108.7
O4—C9—C8	111.6 (4)	O24—C29—C28	111.1 (4)
O4—C9—H9A	109.3	O24—C29—H29A	109.4
C8—C9—H9A	109.3	C28—C29—H29A	109.4
O4—C9—H9B	109.3	O24—C29—H29B	109.4
C8—C9—H9B	109.3	C28—C29—H29B	109.4
H9A—C9—H9B	108.0	H29A—C29—H29B	108.0
O6—C10—O5	122.0 (5)	O26—C30—O25	122.4 (5)
O6—C10—C11	126.8 (5)	O26—C30—C31	125.9 (5)
O5—C10—C11	111.2 (5)	O25—C30—C31	111.6 (5)
C10—C11—H11A	109.5	C30—C31—H31A	109.5
C10—C11—H11B	109.5	C30—C31—H31B	109.5
H11A—C11—H11B	109.5	H31A—C31—H31B	109.5
C10—C11—H11C	109.5	C30—C31—H31C	109.5
H11A—C11—H11C	109.5	H31A—C31—H31C	109.5
H11B—C11—H11C	109.5	H31B—C31—H31C	109.5
C4—N1—C1—O1	179.5 (4)	C24—N21—C21—O21	175.5 (4)
C5—N1—C1—O1	2.5 (6)	C25—N21—C21—O21	4.8 (6)
C4—N1—C1—N2	−3.3 (6)	C24—N21—C21—N22	−4.2 (6)
C5—N1—C1—N2	179.8 (3)	C25—N21—C21—N22	−174.8 (3)
C2—N2—C1—O1	−179.8 (4)	C22—N22—C21—O21	−177.5 (4)
C2—N2—C1—N1	3.0 (6)	C22—N22—C21—N21	2.1 (6)
C1—N2—C2—O2	178.5 (4)	C21—N22—C22—O22	−179.5 (4)
C1—N2—C2—C3	−1.3 (7)	C21—N22—C22—C23	0.1 (7)
O2—C2—C3—C4	−179.8 (5)	O22—C22—C23—C24	179.3 (4)
N2—C2—C3—C4	−0.1 (7)	N22—C22—C23—C24	−0.3 (6)
C2—C3—C4—N1	−0.5 (8)	C22—C23—C24—N21	−1.8 (7)
C1—N1—C4—C3	2.3 (7)	C21—N21—C24—C23	4.3 (6)
C5—N1—C4—C3	179.2 (4)	C25—N21—C24—C23	174.7 (4)
C8—O3—C5—N1	−144.8 (3)	C28—O23—C25—N21	−144.4 (3)
C8—O3—C5—C6	−22.1 (4)	C28—O23—C25—C26	−22.7 (4)
C4—N1—C5—O3	36.1 (5)	C21—N21—C25—O23	−151.1 (3)
C1—N1—C5—O3	−146.9 (3)	C24—N21—C25—O23	38.1 (5)
C4—N1—C5—C6	−81.4 (5)	C21—N21—C25—C26	91.5 (4)
C1—N1—C5—C6	95.6 (5)	C24—N21—C25—C26	−79.3 (5)
O3—C5—C6—C7	31.3 (4)	O23—C25—C26—C27	32.7 (4)
N1—C5—C6—C7	149.2 (3)	N21—C25—C26—C27	151.3 (3)
C10—O5—C7—C8	−78.8 (5)	C30—O25—C27—C26	170.3 (4)
C10—O5—C7—C6	167.8 (3)	C30—O25—C27—C28	−76.3 (5)
C5—C6—C7—O5	90.1 (4)	C25—C26—C27—O25	88.0 (4)
C5—C6—C7—C8	−28.7 (4)	C25—C26—C27—C28	−29.6 (4)
C5—O3—C8—C7	3.2 (4)	C25—O23—C28—C29	128.5 (4)
C5—O3—C8—C9	127.3 (4)	C25—O23—C28—C27	3.6 (4)
O5—C7—C8—O3	−99.0 (4)	O25—C27—C28—O23	−97.5 (4)
C6—C7—C8—O3	16.3 (4)	C26—C27—C28—O23	17.3 (4)
O5—C7—C8—C9	140.2 (4)	O25—C27—C28—C29	141.8 (4)
C6—C7—C8—C9	−104.5 (4)	C26—C27—C28—C29	−103.5 (4)
O3—C8—C9—O4	−72.2 (5)	O23—C28—C29—O24	−68.0 (5)
C7—C8—C9—O4	47.4 (6)	C27—C28—C29—O24	51.4 (5)
C7—O5—C10—O6	5.4 (7)	C27—O25—C30—O26	6.2 (7)
C7—O5—C10—C11	−175.3 (4)	C27—O25—C30—C31	−174.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1···O1i	0.82	1.98	2.798 (5)	173
N2—H2···O22ii	0.86	1.98	2.803 (5)	161
N22—H22···O2ii	0.86	1.99	2.817 (5)	160
O24—H24···O21iii	0.82	2.02	2.828 (5)	170
C3—H3A···O22iv	0.93	2.24	3.117 (6)	157
C23—H23A···O2v	0.93	2.39	3.254 (5)	154
C24—H24A···O21iii	0.93	2.59	3.381 (5)	143
C31—H31B···O26vi	0.96	2.56	3.428 (8)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H1⋯O1i	0.82	1.98	2.798 (5)	173
N2—H2⋯O22ii	0.86	1.98	2.803 (5)	161
N22—H22⋯O2ii	0.86	1.99	2.817 (5)	160
O24—H24⋯O21iii	0.82	2.02	2.828 (5)	170
C3—H3A⋯O22iv	0.93	2.24	3.117 (6)	157
C23—H23A⋯O2v	0.93	2.39	3.254 (5)	154
C24—H24A⋯O21iii	0.93	2.59	3.381 (5)	143
C31—H31B⋯O26vi	0.96	2.56	3.428 (8)	150

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .