3α,6α-Bis(ethoxy-carbon-yl)glycoluril (diethyl 2,5-dioxoperhydro-imidazo[4,5-d]imidazole-3a,6a-dicarboxyl-ate).

The title compound, C(10)H(14)N(4)O(6), crystallizes with two independent mol-ecules in the asymmetric unit. An extensive network of N-H⋯O and C-H⋯O inter-molecular hydrogen bonds stabilizes the crystal packing. One ethyl group is disordered over two positions; the site occupancy factors are 0.68 and 0.32.

Related literature

For related literature, see: Burnett et al. (2003 ▶); Chen et al. (2007 ▶); Himes et al. (1978 ▶); Hof et al. (2002 ▶); Isaacs & Witt (2002 ▶); Kim et al. (2000 ▶); Li et al. (1994 ▶); Moon et al. (2003 ▶); Rowan et al. (1999 ▶); Wang et al. (2006 ▶, 2007 ▶); Wu et al. (2002 ▶).

Experimental

Crystal data

C10H14N4O6

M = 286.25

Orthorhombic,

a = 15.7555 (13) Å

b = 11.2726 (9) Å

c = 28.742 (2) Å

V = 5104.7 (7) Å3

Z = 16

Mo Kα radiation

μ = 0.12 mm−1

T = 292 (2) K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer

Absorption correction: none

29774 measured reflections

4501 independent reflections

2784 reflections with I > 2σ(I)

R int = 0.097

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.197

S = 1.00

4501 reflections

385 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.42 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL (Bruker, 1997 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807056292/cv2340sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807056292/cv2340Isup2.hkl

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

C10H14N4O6	F000 = 2400
Mr = 286.25	Dx = 1.490 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2687 reflections
a = 15.7555 (13) Å	θ = 2.6–23.5º
b = 11.2726 (9) Å	µ = 0.12 mm−1
c = 28.742 (2) Å	T = 292 (2) K
V = 5104.7 (7) Å3	Block, colourless
Z = 16	0.30 × 0.20 × 0.20 mm

Bruker SMART 4K CCD area-detector diffractometer	2784 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.097
Monochromator: graphite	θmax = 25.0º
T = 292(2) K	θmin = 1.9º
φ and ω scans	h = −18→18
Absorption correction: none	k = −11→13
29774 measured reflections	l = −34→29
4501 independent reflections

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)] = 0.068	H-atom parameters constrained
wR(F2) = 0.197	?
S = 1.00	(Δ/σ)max < 0.001
4501 reflections	Δρmax = 0.37 e Å−3
385 parameters	Δρmin = −0.42 e Å−3
6 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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)
C1	0.04208 (19)	0.0660 (3)	0.18565 (10)	0.0315 (8)
C2	−0.0170 (2)	0.4006 (3)	0.18911 (10)	0.0340 (8)
C3	0.0813 (2)	0.2558 (2)	0.21072 (10)	0.0304 (7)
C4	0.1717 (2)	0.2877 (3)	0.22674 (12)	0.0458 (9)
C5	0.3149 (3)	0.2426 (8)	0.2249 (3)	0.048 (2)	0.683 (15)
H5A	0.3278	0.2316	0.2576	0.058*	0.683 (15)
H5B	0.3233	0.3254	0.2170	0.058*	0.683 (15)
C6	0.3700 (4)	0.1644 (8)	0.1953 (4)	0.063 (3)	0.683 (15)
H6A	0.3601	0.0828	0.2033	0.095*	0.683 (15)
H6B	0.4286	0.1835	0.2007	0.095*	0.683 (15)
H6C	0.3566	0.1767	0.1631	0.095*	0.683 (15)
C5'	0.3127 (6)	0.169 (2)	0.2260 (7)	0.082 (7)	0.317 (15)
H5'1	0.3173	0.0833	0.2257	0.098*	0.317 (15)
H5'2	0.3278	0.1970	0.2569	0.098*	0.317 (15)
C6'	0.3725 (8)	0.223 (2)	0.1899 (9)	0.126 (12)	0.317 (15)
H6'1	0.3641	0.1839	0.1605	0.190*	0.317 (15)
H6'2	0.4302	0.2122	0.1997	0.190*	0.317 (15)
H6'3	0.3607	0.3059	0.1866	0.190*	0.317 (15)
C7	0.0685 (2)	0.2544 (2)	0.15577 (10)	0.0314 (8)
C8	0.1431 (2)	0.2921 (3)	0.12516 (13)	0.0504 (10)
C9	0.2477 (3)	0.4440 (4)	0.11294 (16)	0.0836 (15)
H9A	0.2828	0.4932	0.1329	0.100*
H9B	0.2830	0.3815	0.1001	0.100*
C10	0.2119 (3)	0.5147 (4)	0.07577 (17)	0.0965 (17)
H10A	0.1835	0.4638	0.0540	0.145*
H10B	0.2565	0.5569	0.0601	0.145*
H10C	0.1721	0.5704	0.0885	0.145*
C11	0.4936 (2)	0.4078 (3)	0.06138 (11)	0.0347 (8)
C12	0.52703 (19)	0.0688 (3)	0.06489 (10)	0.0301 (7)
C13	0.56575 (19)	0.2511 (2)	0.09612 (10)	0.0296 (7)
C14	0.6371 (2)	0.2861 (3)	0.12889 (12)	0.0420 (9)
C15	0.7460 (3)	0.4299 (4)	0.14264 (16)	0.0771 (14)
H15A	0.7656	0.3726	0.1654	0.093*
H15B	0.7944	0.4544	0.1241	0.093*
C16	0.7102 (3)	0.5323 (4)	0.16631 (17)	0.0867 (16)
H16A	0.6913	0.5892	0.1437	0.130*
H16B	0.7526	0.5678	0.1858	0.130*
H16C	0.6629	0.5076	0.1850	0.130*
C17	0.5822 (2)	0.2525 (2)	0.04197 (10)	0.0296 (7)
C18	0.6762 (2)	0.2567 (3)	0.02697 (11)	0.0391 (8)
C19	0.8066 (2)	0.1494 (4)	0.02685 (19)	0.0847 (16)
H19A	0.8121	0.1722	−0.0056	0.102*
H19B	0.8237	0.0671	0.0296	0.102*
C20	0.8641 (3)	0.2246 (4)	0.05570 (17)	0.0871 (16)
H20A	0.8512	0.3068	0.0505	0.131*
H20B	0.9220	0.2094	0.0471	0.131*
H20C	0.8561	0.2060	0.0880	0.131*
N1	0.05846 (16)	0.1358 (2)	0.22301 (8)	0.0332 (7)
H1	0.0555	0.1110	0.2513	0.040*
N2	0.04634 (17)	0.1327 (2)	0.14663 (8)	0.0367 (7)
H2	0.0368	0.1053	0.1192	0.044*
N3	0.02328 (17)	0.3466 (2)	0.22512 (9)	0.0389 (7)
H3	0.0148	0.3650	0.2538	0.047*
N4	0.00082 (17)	0.3390 (2)	0.14951 (9)	0.0377 (7)
H4	−0.0254	0.3495	0.1236	0.045*
N5	0.49893 (16)	0.3389 (2)	0.09994 (9)	0.0361 (7)
H5	0.4665	0.3463	0.1238	0.043*
N6	0.53960 (17)	0.3573 (2)	0.02693 (9)	0.0375 (7)
H6	0.5428	0.3853	−0.0009	0.045*
N7	0.54036 (16)	0.1301 (2)	0.10487 (8)	0.0341 (7)
H7	0.5344	0.1003	0.1322	0.041*
N8	0.54353 (16)	0.1409 (2)	0.02829 (8)	0.0334 (7)
H8	0.5323	0.1225	−0.0001	0.040*
O1	0.02606 (15)	−0.04068 (18)	0.18682 (7)	0.0417 (6)
O2	−0.06149 (16)	0.48901 (19)	0.19152 (7)	0.0439 (6)
O3	0.18984 (19)	0.3785 (3)	0.24553 (10)	0.0773 (9)
O4	0.22562 (15)	0.2053 (3)	0.21459 (10)	0.0647 (8)
O5	0.17702 (17)	0.3914 (2)	0.14036 (9)	0.0619 (8)
O6	0.1614 (3)	0.2417 (2)	0.09063 (13)	0.1284 (18)
O7	0.45447 (16)	0.50226 (19)	0.05859 (8)	0.0480 (7)
O8	0.50442 (15)	−0.03524 (18)	0.06237 (7)	0.0413 (6)
O9	0.6426 (2)	0.2439 (2)	0.16701 (10)	0.0796 (10)
O10	0.68161 (17)	0.3742 (2)	0.11215 (9)	0.0650 (8)
O11	0.70598 (17)	0.3366 (2)	0.00593 (10)	0.0706 (9)
O12	0.71686 (14)	0.1612 (2)	0.04116 (10)	0.0616 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0399 (18)	0.0296 (18)	0.0250 (18)	−0.0046 (15)	0.0030 (14)	0.0008 (14)
C2	0.048 (2)	0.0267 (18)	0.0273 (18)	−0.0013 (15)	0.0036 (15)	−0.0002 (14)
C3	0.0477 (19)	0.0223 (16)	0.0212 (17)	−0.0032 (14)	0.0050 (14)	−0.0020 (13)
C4	0.054 (2)	0.049 (2)	0.034 (2)	−0.011 (2)	−0.0007 (17)	0.0040 (18)
C5	0.036 (3)	0.051 (5)	0.056 (4)	−0.007 (3)	−0.010 (3)	−0.007 (4)
C6	0.032 (4)	0.059 (6)	0.099 (6)	−0.007 (3)	−0.006 (4)	−0.025 (5)
C5'	0.098 (15)	0.050 (12)	0.098 (14)	−0.022 (11)	−0.021 (11)	0.007 (11)
C6'	0.16 (2)	0.080 (18)	0.14 (2)	−0.066 (16)	0.005 (16)	−0.046 (18)
C7	0.0505 (19)	0.0201 (16)	0.0237 (18)	−0.0023 (14)	0.0048 (14)	0.0012 (13)
C8	0.080 (3)	0.0243 (18)	0.047 (2)	−0.0075 (18)	0.028 (2)	0.0016 (17)
C9	0.093 (3)	0.084 (3)	0.074 (3)	−0.043 (3)	0.018 (3)	0.020 (3)
C10	0.116 (4)	0.104 (4)	0.070 (3)	−0.037 (3)	0.014 (3)	0.021 (3)
C11	0.051 (2)	0.0272 (18)	0.0262 (18)	0.0004 (16)	−0.0031 (15)	−0.0002 (14)
C12	0.0422 (18)	0.0244 (17)	0.0236 (17)	0.0001 (14)	0.0001 (14)	−0.0021 (13)
C13	0.0467 (19)	0.0227 (16)	0.0193 (16)	0.0016 (14)	−0.0029 (14)	0.0000 (13)
C14	0.068 (2)	0.0253 (17)	0.033 (2)	0.0008 (17)	−0.0117 (18)	−0.0028 (16)
C15	0.075 (3)	0.091 (3)	0.065 (3)	−0.045 (3)	−0.010 (2)	−0.018 (3)
C16	0.126 (5)	0.066 (3)	0.068 (3)	−0.024 (3)	−0.025 (3)	0.002 (3)
C17	0.0462 (18)	0.0217 (16)	0.0209 (17)	−0.0002 (14)	−0.0021 (14)	−0.0014 (12)
C18	0.051 (2)	0.036 (2)	0.030 (2)	−0.0069 (17)	0.0047 (16)	−0.0019 (16)
C19	0.055 (3)	0.075 (3)	0.124 (4)	0.008 (2)	0.019 (3)	−0.028 (3)
C20	0.054 (3)	0.119 (4)	0.088 (4)	−0.010 (3)	0.007 (2)	−0.002 (3)
N1	0.0568 (17)	0.0260 (14)	0.0167 (13)	−0.0072 (12)	0.0020 (12)	0.0029 (11)
N2	0.0675 (19)	0.0236 (14)	0.0190 (14)	−0.0060 (13)	0.0017 (13)	−0.0022 (11)
N3	0.0638 (18)	0.0330 (16)	0.0200 (15)	0.0150 (14)	0.0035 (13)	−0.0003 (12)
N4	0.0609 (18)	0.0311 (15)	0.0210 (14)	0.0071 (13)	−0.0028 (13)	−0.0015 (12)
N5	0.0539 (17)	0.0299 (15)	0.0244 (15)	0.0095 (13)	0.0050 (12)	0.0032 (12)
N6	0.0602 (18)	0.0292 (15)	0.0231 (15)	0.0072 (13)	0.0018 (13)	0.0023 (12)
N7	0.0615 (18)	0.0248 (14)	0.0160 (13)	−0.0035 (13)	−0.0016 (12)	0.0017 (11)
N8	0.0534 (17)	0.0297 (14)	0.0170 (13)	−0.0078 (12)	−0.0035 (12)	−0.0005 (11)
O1	0.0726 (17)	0.0228 (12)	0.0297 (13)	−0.0122 (11)	0.0029 (11)	0.0000 (10)
O2	0.0629 (16)	0.0333 (13)	0.0355 (14)	0.0145 (12)	0.0033 (11)	−0.0008 (10)
O3	0.098 (2)	0.0696 (19)	0.065 (2)	−0.0339 (17)	−0.0148 (17)	−0.0141 (17)
O4	0.0439 (15)	0.079 (2)	0.071 (2)	0.0037 (15)	−0.0027 (14)	−0.0057 (17)
O5	0.0844 (19)	0.0537 (16)	0.0475 (16)	−0.0306 (14)	0.0233 (14)	0.0021 (13)
O6	0.202 (4)	0.067 (2)	0.117 (3)	−0.056 (2)	0.124 (3)	−0.054 (2)
O7	0.0780 (18)	0.0339 (14)	0.0320 (13)	0.0195 (13)	−0.0011 (12)	0.0031 (11)
O8	0.0710 (16)	0.0255 (13)	0.0273 (12)	−0.0093 (11)	−0.0039 (11)	−0.0007 (10)
O9	0.133 (3)	0.0509 (17)	0.0548 (19)	−0.0262 (17)	−0.0532 (19)	0.0164 (14)
O10	0.0821 (19)	0.0751 (18)	0.0378 (15)	−0.0376 (16)	−0.0125 (14)	0.0008 (14)
O11	0.0692 (19)	0.083 (2)	0.0593 (19)	−0.0114 (16)	0.0114 (15)	0.0253 (16)
O12	0.0470 (16)	0.0454 (15)	0.092 (2)	0.0059 (12)	0.0072 (14)	−0.0009 (15)

C1—O1	1.229 (4)	C11—N6	1.352 (4)
C1—N2	1.352 (4)	C11—N5	1.357 (4)
C1—N1	1.356 (4)	C12—O8	1.228 (3)
C2—O2	1.220 (4)	C12—N8	1.355 (4)
C2—N3	1.358 (4)	C12—N7	1.357 (4)
C2—N4	1.362 (4)	C13—N7	1.444 (3)
C3—N3	1.433 (4)	C13—N5	1.449 (4)
C3—N1	1.443 (3)	C13—C14	1.519 (4)
C3—C4	1.541 (5)	C13—C17	1.578 (4)
C3—C7	1.592 (4)	C14—O9	1.198 (4)
C4—O3	1.191 (4)	C14—O10	1.308 (4)
C4—O4	1.307 (4)	C15—C16	1.455 (6)
C5—O4	1.497 (5)	C15—O10	1.481 (4)
C5—C6	1.502 (7)	C15—H15A	0.9700
C5—H5A	0.9700	C15—H15B	0.9700
C5—H5B	0.9700	C16—H16A	0.9600
C6—H6A	0.9600	C16—H16B	0.9600
C6—H6B	0.9600	C16—H16C	0.9600
C6—H6C	0.9600	C17—N6	1.426 (4)
C5'—O4	1.469 (9)	C17—N8	1.452 (3)
C5'—C6'	1.527 (10)	C17—C18	1.543 (5)
C5'—H5'1	0.9700	C18—O11	1.182 (4)
C5'—H5'2	0.9700	C18—O12	1.317 (4)
C6'—H6'1	0.9600	C19—O12	1.478 (4)
C6'—H6'2	0.9600	C19—C20	1.493 (6)
C6'—H6'3	0.9600	C19—H19A	0.9700
C7—N2	1.440 (3)	C19—H19B	0.9700
C7—N4	1.442 (4)	C20—H20A	0.9600
C7—C8	1.529 (4)	C20—H20B	0.9600
C8—O6	1.179 (4)	C20—H20C	0.9600
C8—O5	1.314 (4)	N1—H1	0.8600
C9—C10	1.448 (6)	N2—H2	0.8600
C9—O5	1.488 (4)	N3—H3	0.8600
C9—H9A	0.9700	N4—H4	0.8600
C9—H9B	0.9700	N5—H5	0.8600
C10—H10A	0.9600	N6—H6	0.8600
C10—H10B	0.9600	N7—H7	0.8600
C10—H10C	0.9600	N8—H8	0.8600
C11—O7	1.233 (4)
O1—C1—N2	125.2 (3)	O9—C14—O10	126.8 (3)
O1—C1—N1	125.8 (3)	O9—C14—C13	121.2 (3)
N2—C1—N1	108.9 (3)	O10—C14—C13	111.5 (3)
O2—C2—N3	126.2 (3)	C16—C15—O10	110.3 (4)
O2—C2—N4	125.6 (3)	C16—C15—H15A	109.6
N3—C2—N4	108.2 (3)	O10—C15—H15A	109.6
N3—C3—N1	116.1 (3)	C16—C15—H15B	109.6
N3—C3—C4	109.7 (3)	O10—C15—H15B	109.6
N1—C3—C4	112.1 (3)	H15A—C15—H15B	108.1
N3—C3—C7	102.3 (2)	C15—C16—H16A	109.5
N1—C3—C7	101.7 (2)	C15—C16—H16B	109.5
C4—C3—C7	114.6 (2)	H16A—C16—H16B	109.5
O3—C4—O4	125.2 (4)	C15—C16—H16C	109.5
O3—C4—C3	123.9 (3)	H16A—C16—H16C	109.5
O4—C4—C3	110.8 (3)	H16B—C16—H16C	109.5
O4—C5—C6	105.5 (5)	N6—C17—N8	116.0 (2)
O4—C5—H5A	110.6	N6—C17—C18	110.0 (3)
C6—C5—H5A	110.6	N8—C17—C18	110.7 (2)
O4—C5—H5B	110.6	N6—C17—C13	103.3 (2)
C6—C5—H5B	110.6	N8—C17—C13	100.9 (2)
H5A—C5—H5B	108.8	C18—C17—C13	115.7 (2)
O4—C5'—C6'	108.3 (9)	O11—C18—O12	126.0 (3)
O4—C5'—H5'1	110.0	O11—C18—C17	123.2 (3)
C6'—C5'—H5'1	110.0	O12—C18—C17	110.9 (3)
O4—C5'—H5'2	110.0	O12—C19—C20	112.0 (4)
C6'—C5'—H5'2	110.0	O12—C19—H19A	109.2
H5'1—C5'—H5'2	108.4	C20—C19—H19A	109.2
C5'—C6'—H6'1	109.5	O12—C19—H19B	109.2
C5'—C6'—H6'2	109.5	C20—C19—H19B	109.2
H6'1—C6'—H6'2	109.5	H19A—C19—H19B	107.9
C5'—C6'—H6'3	109.5	C19—C20—H20A	109.5
H6'1—C6'—H6'3	109.5	C19—C20—H20B	109.5
H6'2—C6'—H6'3	109.5	H20A—C20—H20B	109.5
N2—C7—N4	115.3 (3)	C19—C20—H20C	109.5
N2—C7—C8	110.3 (3)	H20A—C20—H20C	109.5
N4—C7—C8	108.2 (2)	H20B—C20—H20C	109.5
N2—C7—C3	102.8 (2)	C1—N1—C3	113.4 (2)
N4—C7—C3	102.2 (2)	C1—N1—H1	123.3
C8—C7—C3	118.1 (3)	C3—N1—H1	123.3
O6—C8—O5	126.2 (3)	C1—N2—C7	113.0 (2)
O6—C8—C7	122.6 (3)	C1—N2—H2	123.5
O5—C8—C7	111.0 (3)	C7—N2—H2	123.5
C10—C9—O5	108.6 (4)	C2—N3—C3	113.5 (2)
C10—C9—H9A	110.0	C2—N3—H3	123.3
O5—C9—H9A	110.0	C3—N3—H3	123.3
C10—C9—H9B	110.0	C2—N4—C7	112.7 (3)
O5—C9—H9B	110.0	C2—N4—H4	123.7
H9A—C9—H9B	108.4	C7—N4—H4	123.7
C9—C10—H10A	109.5	C11—N5—C13	112.0 (2)
C9—C10—H10B	109.5	C11—N5—H5	124.0
H10A—C10—H10B	109.5	C13—N5—H5	124.0
C9—C10—H10C	109.5	C11—N6—C17	112.3 (2)
H10A—C10—H10C	109.5	C11—N6—H6	123.9
H10B—C10—H10C	109.5	C17—N6—H6	123.9
O7—C11—N6	125.7 (3)	C12—N7—C13	112.1 (2)
O7—C11—N5	125.4 (3)	C12—N7—H7	124.0
N6—C11—N5	108.9 (3)	C13—N7—H7	124.0
O8—C12—N8	125.7 (3)	C12—N8—C17	113.0 (2)
O8—C12—N7	125.5 (3)	C12—N8—H8	123.5
N8—C12—N7	108.8 (2)	C17—N8—H8	123.5
N7—C13—N5	115.5 (3)	C4—O4—C5'	138.1 (10)
N7—C13—C14	110.0 (2)	C4—O4—C5	111.0 (4)
N5—C13—C14	108.2 (2)	C5'—O4—C5	32.5 (7)
N7—C13—C17	103.1 (2)	C8—O5—C9	117.9 (3)
N5—C13—C17	100.8 (2)	C14—O10—C15	118.2 (3)
C14—C13—C17	119.2 (3)	C18—O12—C19	116.9 (3)
N3—C3—C4—O3	−4.5 (5)	C8—C7—N2—C1	128.3 (3)
N1—C3—C4—O3	−134.9 (3)	C3—C7—N2—C1	1.5 (3)
C7—C3—C4—O3	109.9 (4)	O2—C2—N3—C3	−170.9 (3)
N3—C3—C4—O4	179.0 (3)	N4—C2—N3—C3	9.1 (4)
N1—C3—C4—O4	48.6 (4)	N1—C3—N3—C2	−112.5 (3)
C7—C3—C4—O4	−66.6 (4)	C4—C3—N3—C2	119.2 (3)
N3—C3—C7—N2	−123.9 (2)	C7—C3—N3—C2	−2.8 (3)
N1—C3—C7—N2	−3.6 (3)	O2—C2—N4—C7	167.8 (3)
C4—C3—C7—N2	117.5 (3)	N3—C2—N4—C7	−12.1 (4)
N3—C3—C7—N4	−4.0 (3)	N2—C7—N4—C2	120.5 (3)
N1—C3—C7—N4	116.3 (2)	C8—C7—N4—C2	−115.5 (3)
C4—C3—C7—N4	−122.6 (3)	C3—C7—N4—C2	9.8 (3)
N3—C3—C7—C8	114.5 (3)	O7—C11—N5—C13	−165.3 (3)
N1—C3—C7—C8	−125.2 (3)	N6—C11—N5—C13	13.4 (4)
C4—C3—C7—C8	−4.1 (4)	N7—C13—N5—C11	−127.2 (3)
N2—C7—C8—O6	20.6 (5)	C14—C13—N5—C11	109.0 (3)
N4—C7—C8—O6	−106.4 (5)	C17—C13—N5—C11	−16.9 (3)
C3—C7—C8—O6	138.3 (4)	O7—C11—N6—C17	175.8 (3)
N2—C7—C8—O5	−165.0 (3)	N5—C11—N6—C17	−2.9 (4)
N4—C7—C8—O5	68.0 (4)	N8—C17—N6—C11	101.9 (3)
C3—C7—C8—O5	−47.4 (4)	C18—C17—N6—C11	−131.5 (3)
N7—C13—C14—O9	−30.6 (4)	C13—C17—N6—C11	−7.4 (3)
N5—C13—C14—O9	96.5 (4)	O8—C12—N7—C13	−179.4 (3)
C17—C13—C14—O9	−149.3 (3)	N8—C12—N7—C13	1.2 (3)
N7—C13—C14—O10	157.0 (3)	N5—C13—N7—C12	99.5 (3)
N5—C13—C14—O10	−75.9 (3)	C14—C13—N7—C12	−137.6 (3)
C17—C13—C14—O10	38.3 (4)	C17—C13—N7—C12	−9.5 (3)
N7—C13—C17—N6	133.5 (2)	O8—C12—N8—C17	−170.5 (3)
N5—C13—C17—N6	13.9 (3)	N7—C12—N8—C17	8.9 (4)
C14—C13—C17—N6	−104.2 (3)	N6—C17—N8—C12	−124.7 (3)
N7—C13—C17—N8	13.3 (3)	C18—C17—N8—C12	109.1 (3)
N5—C13—C17—N8	−106.4 (2)	C13—C17—N8—C12	−13.9 (3)
C14—C13—C17—N8	135.5 (3)	O3—C4—O4—C5'	18.8 (11)
N7—C13—C17—C18	−106.2 (3)	C3—C4—O4—C5'	−164.8 (9)
N5—C13—C17—C18	134.2 (3)	O3—C4—O4—C5	−3.3 (6)
C14—C13—C17—C18	16.0 (4)	C3—C4—O4—C5	173.1 (4)
N6—C17—C18—O11	−0.3 (4)	C6'—C5'—O4—C4	−96 (2)
N8—C17—C18—O11	129.2 (3)	C6'—C5'—O4—C5	−55.2 (16)
C13—C17—C18—O11	−116.8 (4)	C6—C5—O4—C4	−160.8 (7)
N6—C17—C18—O12	179.1 (3)	C6—C5—O4—C5'	47.1 (14)
N8—C17—C18—O12	−51.4 (3)	O6—C8—O5—C9	−2.7 (7)
C13—C17—C18—O12	62.6 (3)	C7—C8—O5—C9	−176.8 (3)
O1—C1—N1—C3	175.7 (3)	C10—C9—O5—C8	84.3 (5)
N2—C1—N1—C3	−4.2 (4)	O9—C14—O10—C15	−0.1 (6)
N3—C3—N1—C1	114.9 (3)	C13—C14—O10—C15	171.7 (3)
C4—C3—N1—C1	−118.0 (3)	C16—C15—O10—C14	−94.1 (4)
C7—C3—N1—C1	4.8 (3)	O11—C18—O12—C19	−4.2 (5)
O1—C1—N2—C7	−178.5 (3)	C17—C18—O12—C19	176.4 (3)
N1—C1—N2—C7	1.4 (4)	C20—C19—O12—C18	78.4 (5)
N4—C7—N2—C1	−108.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	2.15	2.963 (3)	158
N2—H2···O7ii	0.86	2.10	2.927 (3)	162
N3—H3···O1iii	0.86	2.11	2.937 (3)	161
N4—H4···O8iv	0.86	2.21	2.879 (3)	134
N5—H5···O1iv	0.86	2.22	2.870 (3)	133
N6—H6···O7v	0.86	2.09	2.925 (3)	164
N7—H7···O2ii	0.86	2.16	2.973 (3)	158
N8—H8···O8vi	0.86	2.12	2.963 (3)	165
C16—H16C···O3vii	0.96	2.51	3.087 (5)	119
C10—H10B···O11v	0.96	2.32	3.162 (5)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	2.15	2.963 (3)	158
N2—H2⋯O7ii	0.86	2.10	2.927 (3)	162
N3—H3⋯O1iii	0.86	2.11	2.937 (3)	161
N4—H4⋯O8iv	0.86	2.21	2.879 (3)	134
N5—H5⋯O1iv	0.86	2.22	2.870 (3)	133
N6—H6⋯O7v	0.86	2.09	2.925 (3)	164
N7—H7⋯O2ii	0.86	2.16	2.973 (3)	158
N8—H8⋯O8vi	0.86	2.12	2.963 (3)	165
C16—H16C⋯O3vii	0.96	2.51	3.087 (5)	119
C10—H10B⋯O11v	0.96	2.32	3.162 (5)	146

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