[(2R,3S,5R)-3-Acet-oxy-5-(5-formyl-2,4-dioxo-1,2,3,4-tetra-hydro-pyrimidin-1-yl)-2,3,4,5-tetra-hydro-furan-2-yl]methyl acetate.

In the two independent but very similar mol-ecules (A and B) of the title compound, C(14)H(16)N(2)O(8), both six-membered pyrimidine rings are nearly planar [maximum deviations = 0.010 (3) Å in A and 0.028 (3) Å in B]. The five-membered furan-ose ring in mol-ecule A adopts an envelope conformation, while the same ring in mol-ecule B has a twisted conformation. In the crystal, the A mol-ecules are linked via a pair of inter-molecular N-H⋯O hydrogen bonds, forming dimers. Each A mol-ecule is further linked to a B mol-ecule via a second N-H⋯O hydrogen bond. There are also a number of C-H⋯·O inter-actions present, leading to the formation of a three-dimensional network.

Related literature

For the bioactivity of 5-substituted pyrimidine nucleosides, see: De Clercq (2005 ▶); Agrofoglio et al. (2003 ▶); Lee et al. (2009 ▶). For the use of the title compound as a synthon for the preparation of a variety of nucleoside derivatives, see: Fan et al. (2006a ▶,b ▶, 2010 ▶, 2011 ▶); Zhang et al. (2009 ▶). For related structures of uridines, see: Luo et al. (2007 ▶); Low & Wilson (1984 ▶).

Experimental

Crystal data

C28H32N4O16

M = 680.58

Orthorhombic,

a = 15.5268 (18) Å

b = 29.977 (4) Å

c = 6.6207 (8) Å

V = 3081.6 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 296 K

0.24 × 0.18 × 0.09 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.971, T max = 0.989

23677 measured reflections

5719 independent reflections

3519 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.110

S = 1.01

5719 reflections

437 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 2320 Friedel pairs

Flack parameter: −0.6 (12)

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811041304/su2320sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811041304/su2320Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811041304/su2320Isup3.cml

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

C28H32N4O16	Dx = 1.467 Mg m−3
Mr = 680.58	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P21212	Cell parameters from 2422 reflections
a = 15.5268 (18) Å	θ = 2.4–18.6°
b = 29.977 (4) Å	µ = 0.12 mm−1
c = 6.6207 (8) Å	T = 296 K
V = 3081.6 (6) Å3	Block, colourless
Z = 4	0.24 × 0.18 × 0.09 mm
F(000) = 1424

Bruker SMART CCD area-detector diffractometer	5719 independent reflections
Radiation source: fine-focus sealed tube	3519 reflections with I > 2σ(I)
graphite	Rint = 0.060
φ and ω scans	θmax = 25.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −18→18
Tmin = 0.971, Tmax = 0.989	k = −36→36
23677 measured reflections	l = −8→8

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.0461P)2 + 0.0767P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
5719 reflections	Δρmax = 0.14 e Å−3
437 parameters	Δρmin = −0.17 e Å−3
0 restraints	Absolute structure: Flack (1983), 2320 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.6 (12)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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	0.86095 (13)	0.15062 (7)	−0.1052 (3)	0.0481 (8)
O2	0.92305 (14)	0.23904 (7)	−0.0130 (4)	0.0536 (8)
O3	0.9059 (2)	0.31223 (8)	−0.0547 (5)	0.0973 (13)
O4	0.69953 (13)	0.16685 (7)	0.1642 (3)	0.0460 (8)
O5	0.68476 (16)	0.19298 (8)	0.4790 (4)	0.0634 (9)
O6	0.91976 (14)	0.03929 (7)	0.0972 (4)	0.0597 (9)
O7	1.20552 (15)	0.06592 (8)	0.0540 (4)	0.0742 (10)
O8	1.17118 (16)	0.20098 (9)	0.0293 (5)	0.0822 (11)
N1	0.96297 (14)	0.11188 (8)	0.0831 (4)	0.0430 (9)
N2	1.06276 (15)	0.05417 (8)	0.0818 (4)	0.0488 (10)
C1	0.87385 (18)	0.12800 (9)	0.0809 (5)	0.0428 (11)
C2	0.85180 (19)	0.16088 (10)	0.2454 (5)	0.0440 (11)
C3	0.78276 (17)	0.18915 (10)	0.1481 (5)	0.0418 (11)
C4	0.80634 (19)	0.18894 (10)	−0.0762 (5)	0.0421 (11)
C5	0.8510 (2)	0.23042 (11)	−0.1460 (5)	0.0540 (12)
C6	0.9448 (2)	0.28190 (13)	0.0199 (6)	0.0603 (14)
C7	1.0206 (2)	0.28489 (12)	0.1526 (7)	0.0803 (19)
C8	0.6580 (2)	0.17068 (11)	0.3399 (6)	0.0467 (11)
C9	0.5770 (2)	0.14428 (12)	0.3443 (6)	0.0717 (16)
C10	0.9779 (2)	0.06618 (10)	0.0875 (5)	0.0448 (11)
C11	1.1334 (2)	0.08179 (11)	0.0667 (5)	0.0493 (12)
C12	1.11258 (18)	0.12880 (10)	0.0623 (5)	0.0419 (11)
C13	1.03017 (19)	0.14162 (10)	0.0667 (5)	0.0446 (11)
C14	1.1828 (2)	0.16136 (13)	0.0510 (5)	0.0550 (12)
O9	1.01699 (14)	0.43238 (7)	0.3062 (3)	0.0513 (8)
O10	1.01223 (18)	0.44857 (9)	−0.0227 (4)	0.0786 (11)
O11	0.78072 (14)	0.48878 (7)	0.5019 (4)	0.0563 (9)
O12	0.76091 (17)	0.55682 (9)	0.6310 (5)	0.0820 (11)
O13	0.83321 (16)	0.28502 (7)	0.4225 (4)	0.0648 (10)
O14	0.54241 (17)	0.29279 (9)	0.4668 (5)	0.0914 (14)
O15	0.54287 (16)	0.42833 (10)	0.4218 (5)	0.0932 (13)
O16	0.85943 (14)	0.40460 (7)	0.5944 (3)	0.0543 (8)
N3	0.77201 (16)	0.35465 (8)	0.4263 (4)	0.0470 (10)
N4	0.68780 (19)	0.29072 (9)	0.4549 (4)	0.0581 (11)
C15	0.85591 (19)	0.37705 (10)	0.4219 (5)	0.0488 (11)
C16	0.8695 (2)	0.40735 (11)	0.2421 (5)	0.0483 (12)
C17	0.9270 (2)	0.44370 (11)	0.3260 (5)	0.0446 (11)
C18	0.9070 (2)	0.44455 (10)	0.5522 (5)	0.0444 (11)
C19	0.8576 (2)	0.48391 (10)	0.6264 (5)	0.0533 (12)
C20	1.0522 (2)	0.43648 (12)	0.1203 (6)	0.0550 (14)
C21	1.1458 (2)	0.42467 (15)	0.1230 (7)	0.0840 (18)
C22	0.7370 (2)	0.52717 (13)	0.5227 (6)	0.0597 (14)
C23	0.6581 (2)	0.52785 (13)	0.3963 (8)	0.0840 (19)
C24	0.7698 (2)	0.30800 (11)	0.4335 (5)	0.0503 (12)
C25	0.6102 (2)	0.31309 (13)	0.4535 (5)	0.0610 (14)
C26	0.6196 (2)	0.36078 (11)	0.4387 (5)	0.0497 (12)
C27	0.6985 (2)	0.37920 (11)	0.4317 (5)	0.0477 (12)
C28	0.5422 (2)	0.38840 (15)	0.4283 (6)	0.0667 (16)
H1	0.83450	0.10250	0.08870	0.0510*
H2	1.07330	0.02600	0.08830	0.0590*
H2A	0.90150	0.17870	0.28230	0.0530*
H2B	0.83010	0.14580	0.36460	0.0530*
H3	0.78130	0.21940	0.20390	0.0500*
H4	0.75370	0.18490	−0.15560	0.0510*
H5A	0.87120	0.22660	−0.28350	0.0650*
H5B	0.81130	0.25540	−0.14320	0.0650*
H7A	1.03510	0.31570	0.17400	0.1210*
H7B	1.06840	0.26990	0.09040	0.1210*
H7C	1.00790	0.27110	0.28000	0.1210*
H9A	0.58980	0.11390	0.37930	0.1080*
H9B	0.55020	0.14520	0.21360	0.1080*
H9C	0.53850	0.15670	0.44290	0.1080*
H13	1.01770	0.17190	0.05840	0.0530*
H14	1.23920	0.15110	0.06090	0.0660*
H4A	0.68480	0.26230	0.47120	0.0700*
H15	0.90210	0.35480	0.42780	0.0590*
H16A	0.81530	0.41950	0.19440	0.0580*
H16B	0.89750	0.39160	0.13220	0.0580*
H17	0.91440	0.47260	0.26310	0.0540*
H18	0.96160	0.44320	0.62610	0.0530*
H19A	0.84140	0.47960	0.76650	0.0640*
H19B	0.89270	0.51060	0.61720	0.0640*
H21A	1.15370	0.39560	0.06520	0.1270*
H21B	1.16630	0.42470	0.25980	0.1270*
H21C	1.17760	0.44620	0.04560	0.1270*
H23A	0.61210	0.51320	0.46680	0.1260*
H23B	0.66910	0.51260	0.27130	0.1260*
H23C	0.64210	0.55820	0.36890	0.1260*
H27	0.70300	0.41010	0.43060	0.0580*
H28	0.48900	0.37410	0.42670	0.0800*

	U11	U22	U33	U12	U13	U23
O1	0.0548 (13)	0.0426 (12)	0.0468 (14)	0.0117 (10)	0.0016 (12)	0.0004 (11)
O2	0.0525 (14)	0.0384 (13)	0.0699 (16)	−0.0016 (11)	0.0001 (12)	0.0071 (11)
O3	0.106 (2)	0.0449 (15)	0.141 (3)	0.0053 (15)	−0.016 (2)	0.0169 (19)
O4	0.0391 (12)	0.0470 (13)	0.0520 (14)	−0.0058 (11)	0.0035 (11)	−0.0026 (11)
O5	0.0716 (16)	0.0605 (15)	0.0581 (17)	−0.0130 (13)	0.0144 (14)	−0.0046 (14)
O6	0.0457 (13)	0.0382 (12)	0.0953 (19)	0.0004 (11)	0.0056 (14)	0.0012 (13)
O7	0.0418 (14)	0.0747 (17)	0.106 (2)	0.0114 (12)	0.0074 (14)	0.0057 (16)
O8	0.0690 (17)	0.0746 (19)	0.103 (2)	−0.0171 (15)	0.0077 (16)	−0.0053 (18)
N1	0.0351 (14)	0.0342 (14)	0.0596 (18)	0.0014 (12)	−0.0003 (14)	0.0043 (14)
N2	0.0433 (16)	0.0388 (14)	0.0642 (19)	0.0056 (12)	0.0039 (15)	0.0038 (15)
C1	0.0379 (18)	0.0356 (17)	0.055 (2)	0.0017 (14)	−0.0010 (17)	0.0048 (18)
C2	0.0378 (19)	0.050 (2)	0.0441 (19)	−0.0007 (16)	−0.0002 (15)	0.0034 (17)
C3	0.0336 (18)	0.0367 (17)	0.055 (2)	−0.0043 (14)	0.0011 (15)	0.0000 (16)
C4	0.0408 (17)	0.0406 (18)	0.045 (2)	0.0074 (15)	−0.0028 (16)	0.0008 (17)
C5	0.057 (2)	0.051 (2)	0.054 (2)	0.0015 (17)	−0.0032 (18)	0.0143 (17)
C6	0.062 (2)	0.048 (2)	0.071 (3)	−0.0061 (19)	0.012 (2)	0.004 (2)
C7	0.073 (3)	0.064 (3)	0.104 (4)	−0.014 (2)	0.002 (3)	−0.005 (2)
C8	0.045 (2)	0.0421 (19)	0.053 (2)	0.0000 (16)	0.0072 (18)	0.0053 (18)
C9	0.054 (2)	0.082 (3)	0.079 (3)	−0.019 (2)	0.015 (2)	0.002 (2)
C10	0.0403 (19)	0.045 (2)	0.049 (2)	0.0067 (16)	0.0017 (17)	−0.0023 (17)
C11	0.044 (2)	0.058 (2)	0.046 (2)	0.0049 (18)	0.0029 (17)	−0.0002 (18)
C12	0.0345 (17)	0.055 (2)	0.0363 (19)	−0.0038 (15)	0.0058 (15)	−0.0023 (17)
C13	0.048 (2)	0.0408 (17)	0.045 (2)	−0.0033 (16)	−0.0003 (17)	−0.0025 (17)
C14	0.047 (2)	0.061 (2)	0.057 (2)	−0.0062 (18)	0.0075 (18)	−0.006 (2)
O9	0.0400 (13)	0.0585 (15)	0.0554 (15)	0.0020 (11)	−0.0022 (11)	−0.0017 (12)
O10	0.0779 (19)	0.101 (2)	0.0569 (17)	0.0079 (16)	0.0026 (15)	0.0083 (16)
O11	0.0516 (14)	0.0516 (15)	0.0658 (16)	0.0085 (12)	−0.0076 (12)	−0.0083 (12)
O12	0.083 (2)	0.0629 (17)	0.100 (2)	0.0161 (15)	0.0022 (17)	−0.0230 (17)
O13	0.0690 (16)	0.0471 (14)	0.0783 (19)	0.0118 (13)	0.0046 (15)	0.0023 (14)
O14	0.0703 (19)	0.092 (2)	0.112 (3)	−0.0347 (16)	0.0091 (17)	0.0173 (18)
O15	0.0596 (18)	0.092 (2)	0.128 (3)	0.0150 (16)	0.0063 (17)	0.003 (2)
O16	0.0700 (15)	0.0476 (13)	0.0452 (14)	−0.0095 (12)	−0.0084 (13)	0.0002 (11)
N3	0.0451 (16)	0.0400 (16)	0.0560 (18)	−0.0013 (13)	−0.0042 (15)	0.0018 (14)
N4	0.070 (2)	0.0442 (16)	0.060 (2)	−0.0129 (16)	0.0094 (17)	0.0077 (15)
C15	0.0461 (19)	0.0424 (18)	0.058 (2)	−0.0013 (15)	−0.0072 (18)	−0.0066 (19)
C16	0.043 (2)	0.056 (2)	0.046 (2)	−0.0068 (17)	−0.0020 (16)	−0.0090 (17)
C17	0.039 (2)	0.0429 (19)	0.052 (2)	0.0010 (16)	−0.0065 (16)	0.0002 (17)
C18	0.0422 (18)	0.0400 (18)	0.051 (2)	0.0000 (15)	−0.0083 (16)	−0.0029 (17)
C19	0.051 (2)	0.053 (2)	0.056 (2)	0.0004 (17)	−0.0097 (18)	−0.0086 (17)
C20	0.053 (2)	0.055 (2)	0.057 (3)	−0.0045 (18)	0.003 (2)	−0.012 (2)
C21	0.052 (2)	0.123 (4)	0.077 (3)	0.003 (2)	0.010 (2)	−0.029 (3)
C22	0.056 (2)	0.057 (2)	0.066 (3)	0.010 (2)	0.016 (2)	−0.002 (2)
C23	0.061 (3)	0.082 (3)	0.109 (4)	0.019 (2)	−0.014 (3)	−0.005 (3)
C24	0.062 (2)	0.045 (2)	0.044 (2)	−0.0091 (18)	0.0033 (19)	−0.0013 (19)
C25	0.057 (2)	0.076 (3)	0.050 (2)	−0.012 (2)	0.0037 (19)	0.005 (2)
C26	0.046 (2)	0.063 (2)	0.040 (2)	−0.0008 (18)	−0.0004 (17)	0.0042 (18)
C27	0.049 (2)	0.050 (2)	0.044 (2)	0.0031 (17)	−0.0029 (17)	−0.0006 (17)
C28	0.055 (2)	0.088 (3)	0.057 (3)	−0.004 (2)	0.007 (2)	0.008 (3)

O1—C1	1.421 (4)	C12—C13	1.336 (4)
O1—C4	1.441 (4)	C12—C14	1.465 (5)
O2—C5	1.447 (4)	C1—H1	0.9800
O2—C6	1.346 (4)	C2—H2B	0.9700
O3—C6	1.198 (5)	C2—H2A	0.9700
O4—C3	1.459 (3)	C3—H3	0.9800
O4—C8	1.335 (4)	C4—H4	0.9800
O5—C8	1.212 (4)	C5—H5A	0.9700
O6—C10	1.212 (4)	C5—H5B	0.9700
O7—C11	1.220 (4)	C7—H7A	0.9600
O8—C14	1.210 (5)	C7—H7C	0.9600
O9—C20	1.352 (4)	C7—H7B	0.9600
O9—C17	1.444 (4)	C9—H9B	0.9600
O10—C20	1.189 (5)	C9—H9C	0.9600
O11—C22	1.343 (4)	C9—H9A	0.9600
O11—C19	1.458 (4)	C13—H13	0.9300
O12—C22	1.201 (5)	C14—H14	0.9300
O13—C24	1.204 (4)	C15—C16	1.512 (5)
O14—C25	1.219 (4)	C16—C17	1.514 (5)
O15—C28	1.198 (5)	C17—C18	1.530 (5)
O16—C18	1.435 (4)	C18—C19	1.491 (4)
O16—C15	1.411 (4)	C20—C21	1.496 (4)
N1—C10	1.390 (4)	C22—C23	1.484 (5)
N1—C13	1.377 (4)	C25—C26	1.440 (5)
N1—C1	1.466 (4)	C26—C27	1.345 (4)
N2—C10	1.366 (4)	C26—C28	1.461 (5)
N2—C11	1.378 (4)	C15—H15	0.9800
N2—H2	0.8600	C16—H16A	0.9700
N3—C15	1.466 (4)	C16—H16B	0.9700
N3—C24	1.400 (4)	C17—H17	0.9800
N3—C27	1.359 (4)	C18—H18	0.9800
N4—C24	1.382 (4)	C19—H19A	0.9700
N4—C25	1.379 (4)	C19—H19B	0.9700
N4—H4A	0.8600	C21—H21A	0.9600
C1—C2	1.508 (4)	C21—H21B	0.9600
C2—C3	1.511 (4)	C21—H21C	0.9600
C3—C4	1.530 (5)	C23—H23A	0.9600
C4—C5	1.497 (4)	C23—H23B	0.9600
C6—C7	1.471 (5)	C23—H23C	0.9600
C8—C9	1.486 (5)	C27—H27	0.9300
C11—C12	1.446 (4)	C28—H28	0.9300
C1—O1—C4	110.4 (2)	H9A—C9—H9B	110.00
C5—O2—C6	117.6 (3)	H9A—C9—H9C	109.00
C3—O4—C8	116.9 (2)	H9B—C9—H9C	109.00
C17—O9—C20	116.9 (2)	C8—C9—H9A	110.00
C19—O11—C22	116.2 (3)	C8—C9—H9B	109.00
C15—O16—C18	110.6 (2)	N1—C13—H13	119.00
C10—N1—C13	120.9 (2)	C12—C13—H13	119.00
C1—N1—C10	118.9 (2)	O8—C14—H14	118.00
C1—N1—C13	120.1 (2)	C12—C14—H14	118.00
C10—N2—C11	127.7 (3)	O16—C15—C16	106.3 (2)
C11—N2—H2	116.00	N3—C15—C16	114.5 (3)
C10—N2—H2	116.00	O16—C15—N3	106.7 (2)
C24—N3—C27	121.3 (3)	C15—C16—C17	103.1 (3)
C15—N3—C24	118.7 (2)	O9—C17—C18	106.8 (2)
C15—N3—C27	119.9 (2)	O9—C17—C16	111.6 (3)
C24—N4—C25	128.5 (3)	C16—C17—C18	104.6 (3)
C24—N4—H4A	116.00	O16—C18—C19	109.4 (2)
C25—N4—H4A	116.00	C17—C18—C19	116.1 (3)
O1—C1—N1	107.4 (2)	O16—C18—C17	106.3 (2)
N1—C1—C2	115.0 (2)	O11—C19—C18	108.3 (3)
O1—C1—C2	106.4 (2)	O9—C20—C21	111.1 (3)
C1—C2—C3	102.7 (3)	O9—C20—O10	122.8 (3)
O4—C3—C4	106.3 (2)	O10—C20—C21	126.1 (4)
C2—C3—C4	104.0 (2)	O12—C22—C23	125.6 (3)
O4—C3—C2	109.9 (2)	O11—C22—C23	111.8 (3)
O1—C4—C3	105.9 (2)	O11—C22—O12	122.6 (3)
O1—C4—C5	110.4 (2)	O13—C24—N3	123.3 (3)
C3—C4—C5	114.0 (3)	O13—C24—N4	123.0 (3)
O2—C5—C4	108.6 (3)	N3—C24—N4	113.6 (3)
O2—C6—C7	110.8 (3)	O14—C25—N4	120.7 (3)
O2—C6—O3	122.1 (3)	N4—C25—C26	113.2 (3)
O3—C6—C7	127.1 (4)	O14—C25—C26	126.0 (3)
O5—C8—C9	124.7 (3)	C25—C26—C28	118.8 (3)
O4—C8—O5	123.0 (3)	C25—C26—C27	120.2 (3)
O4—C8—C9	112.3 (3)	C27—C26—C28	121.0 (3)
N1—C10—N2	114.8 (3)	N3—C27—C26	123.0 (3)
O6—C10—N2	123.0 (3)	O15—C28—C26	124.1 (3)
O6—C10—N1	122.2 (3)	O16—C15—H15	110.00
N2—C11—C12	114.2 (3)	N3—C15—H15	110.00
O7—C11—N2	120.1 (3)	C16—C15—H15	110.00
O7—C11—C12	125.7 (3)	C15—C16—H16A	111.00
C13—C12—C14	121.5 (3)	C15—C16—H16B	111.00
C11—C12—C14	118.9 (3)	C17—C16—H16A	111.00
C11—C12—C13	119.6 (3)	C17—C16—H16B	111.00
N1—C13—C12	122.8 (3)	H16A—C16—H16B	109.00
O8—C14—C12	123.3 (3)	O9—C17—H17	111.00
N1—C1—H1	109.00	C16—C17—H17	111.00
O1—C1—H1	109.00	C18—C17—H17	111.00
C2—C1—H1	109.00	O16—C18—H18	108.00
H2A—C2—H2B	109.00	C17—C18—H18	108.00
C3—C2—H2B	111.00	C19—C18—H18	108.00
C3—C2—H2A	111.00	O11—C19—H19A	110.00
C1—C2—H2B	111.00	O11—C19—H19B	110.00
C1—C2—H2A	111.00	C18—C19—H19A	110.00
O4—C3—H3	112.00	C18—C19—H19B	110.00
C4—C3—H3	112.00	H19A—C19—H19B	108.00
C2—C3—H3	112.00	C20—C21—H21A	110.00
C5—C4—H4	109.00	C20—C21—H21B	109.00
O1—C4—H4	109.00	C20—C21—H21C	110.00
C3—C4—H4	109.00	H21A—C21—H21B	110.00
O2—C5—H5B	110.00	H21A—C21—H21C	109.00
O2—C5—H5A	110.00	H21B—C21—H21C	109.00
H5A—C5—H5B	108.00	C22—C23—H23A	110.00
C4—C5—H5A	110.00	C22—C23—H23B	109.00
C4—C5—H5B	110.00	C22—C23—H23C	109.00
C6—C7—H7B	109.00	H23A—C23—H23B	109.00
C6—C7—H7C	110.00	H23A—C23—H23C	109.00
H7A—C7—H7B	109.00	H23B—C23—H23C	110.00
H7A—C7—H7C	109.00	N3—C27—H27	118.00
H7B—C7—H7C	110.00	C26—C27—H27	119.00
C6—C7—H7A	110.00	O15—C28—H28	118.00
C8—C9—H9C	109.00	C26—C28—H28	118.00
C4—O1—C1—N1	−142.9 (2)	C24—N3—C15—O16	−120.1 (3)
C4—O1—C1—C2	−19.2 (3)	C27—N3—C15—O16	57.3 (4)
C1—O1—C4—C5	122.9 (3)	C24—N3—C15—C16	122.7 (3)
C1—O1—C4—C3	−1.0 (3)	C24—N4—C25—C26	−3.8 (5)
C5—O2—C6—C7	−178.2 (3)	C24—N4—C25—O14	177.2 (3)
C6—O2—C5—C4	−147.9 (3)	C25—N4—C24—N3	5.6 (5)
C5—O2—C6—O3	1.0 (5)	C25—N4—C24—O13	−174.5 (3)
C8—O4—C3—C4	−167.3 (2)	O1—C1—C2—C3	31.3 (3)
C3—O4—C8—O5	3.2 (4)	N1—C1—C2—C3	150.1 (2)
C8—O4—C3—C2	80.8 (3)	C1—C2—C3—C4	−31.0 (3)
C3—O4—C8—C9	−176.2 (3)	C1—C2—C3—O4	82.5 (3)
C17—O9—C20—C21	178.7 (3)	C2—C3—C4—C5	−101.1 (3)
C20—O9—C17—C18	−170.0 (3)	O4—C3—C4—O1	−95.5 (2)
C17—O9—C20—O10	−0.3 (5)	C2—C3—C4—O1	20.5 (3)
C20—O9—C17—C16	76.3 (3)	O4—C3—C4—C5	142.9 (2)
C19—O11—C22—O12	2.9 (5)	C3—C4—C5—O2	51.7 (3)
C22—O11—C19—C18	−168.1 (3)	O1—C4—C5—O2	−67.3 (3)
C19—O11—C22—C23	−177.5 (3)	O7—C11—C12—C13	176.4 (3)
C18—O16—C15—N3	−146.0 (2)	O7—C11—C12—C14	−3.0 (5)
C18—O16—C15—C16	−23.4 (3)	N2—C11—C12—C14	178.7 (3)
C15—O16—C18—C19	132.3 (3)	N2—C11—C12—C13	−2.0 (5)
C15—O16—C18—C17	6.1 (3)	C13—C12—C14—O8	−5.9 (5)
C10—N1—C1—O1	−116.1 (3)	C11—C12—C13—N1	2.5 (5)
C13—N1—C1—C2	−58.8 (4)	C11—C12—C14—O8	173.5 (3)
C13—N1—C10—N2	2.3 (4)	C14—C12—C13—N1	−178.1 (3)
C10—N1—C1—C2	125.7 (3)	O16—C15—C16—C17	30.7 (3)
C13—N1—C10—O6	−178.3 (3)	N3—C15—C16—C17	148.1 (3)
C1—N1—C10—N2	177.7 (3)	C15—C16—C17—O9	88.9 (3)
C1—N1—C13—C12	−178.1 (3)	C15—C16—C17—C18	−26.2 (3)
C1—N1—C10—O6	−2.8 (5)	C16—C17—C18—O16	13.4 (3)
C10—N1—C13—C12	−2.7 (5)	O9—C17—C18—O16	−105.0 (3)
C13—N1—C1—O1	59.4 (3)	C16—C17—C18—C19	−108.6 (3)
C11—N2—C10—N1	−2.0 (5)	O9—C17—C18—C19	133.0 (3)
C11—N2—C10—O6	178.6 (3)	C17—C18—C19—O11	52.1 (3)
C10—N2—C11—O7	−176.6 (3)	O16—C18—C19—O11	−68.2 (3)
C10—N2—C11—C12	1.8 (5)	O14—C25—C26—C27	177.7 (4)
C15—N3—C24—N4	174.7 (3)	N4—C25—C26—C28	177.8 (3)
C15—N3—C24—O13	−5.2 (5)	O14—C25—C26—C28	−3.2 (5)
C27—N3—C24—N4	−2.6 (4)	N4—C25—C26—C27	−1.2 (5)
C27—N3—C24—O13	177.5 (3)	C25—C26—C27—N3	3.9 (5)
C24—N3—C27—C26	−1.8 (5)	C27—C26—C28—O15	−3.3 (6)
C27—N3—C15—C16	−60.0 (4)	C28—C26—C27—N3	−175.1 (3)
C15—N3—C27—C26	−179.1 (3)	C25—C26—C28—O15	177.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O6i	0.86	1.96	2.817 (3)	172
N4—H4A···O5	0.86	2.08	2.935 (4)	173
C3—H3···O13	0.98	2.57	3.489 (4)	156
C13—H13···O2	0.93	2.54	3.402 (4)	155
C16—H16A···O7ii	0.97	2.41	3.312 (4)	155
C18—H18···O10iii	0.98	2.46	3.257 (4)	138
C21—H21A···O4iv	0.96	2.51	3.441 (5)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O6i	0.86	1.96	2.817 (3)	172
N4—H4A⋯O5	0.86	2.08	2.935 (4)	173
C3—H3⋯O13	0.98	2.57	3.489 (4)	156
C13—H13⋯O2	0.93	2.54	3.402 (4)	155
C16—H16A⋯O7ii	0.97	2.41	3.312 (4)	155
C18—H18⋯O10iii	0.98	2.46	3.257 (4)	138
C21—H21A⋯O4iv	0.96	2.51	3.441 (5)	162

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