Diethyl 2-tert-butyl-4,11-dioxo-2,3-di-hydro-cis-1H,5H,10H-2,3a,4a,10a,11a-penta-azabenzo[f]indeno[2,1,7-ija]azulene-11b,11c-dicarboxyl-ate.

In the title mol-ecule, C(24)H(31)N(5)O(6), the two ethyl fragments are each disordered over two conformations [occupancy ratios 0.58 (13)/0.42 (13) and 0.56 (12)/0.44 (12)]. The crystal packing exhibits inter-molecular non-classical C-H⋯O hydrogen bonds and π-π inter-actions between benzene rings [centroid-centroid distances = 3.836 (5) Å].

Related literature

For the preparation of the title compound, see: Wu et al. (2002 ▶). For crystal engineering studies on glycoluril and its derivatives, see Chen et al. (2007 ▶); Wang et al. (2006 ▶).

Experimental

Crystal data

C24H31N5O6

M = 485.54

Triclinic,

a = 10.7133 (14) Å

b = 11.1013 (15) Å

c = 11.3352 (15) Å

α = 100.493 (2)°

β = 105.438 (2)°

γ = 102.445 (2)°

V = 1227.2 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 292 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer

9853 measured reflections

4253 independent reflections

2734 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.195

S = 1.03

4253 reflections

397 parameters

99 restraints

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1999 ▶); 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 datablocks I, global. DOI: 10.1107/S1600536810000097/cv2681sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000097/cv2681Isup2.hkl

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

C24H31N5O6	Z = 2
Mr = 485.54	F(000) = 516
Triclinic, P1	Dx = 1.314 Mg m−3
a = 10.7133 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.1013 (15) Å	Cell parameters from 2728 reflections
c = 11.3352 (15) Å	θ = 2.3–23.3°
α = 100.493 (2)°	µ = 0.10 mm−1
β = 105.438 (2)°	T = 292 K
γ = 102.445 (2)°	Block, colourless
V = 1227.2 (3) Å3	0.30 × 0.20 × 0.20 mm

Bruker SMART 4K CCD area-detector diffractometer	2734 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.051
graphite	θmax = 25.0°, θmin = 1.9°
phi and ω scans	h = −12→12
9853 measured reflections	k = −13→13
4253 independent reflections	l = −13→13

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.195	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.116P)2] where P = (Fo2 + 2Fc2)/3
4253 reflections	(Δ/σ)max < 0.001
397 parameters	Δρmax = 0.46 e Å−3
99 restraints	Δρmin = −0.27 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)
C1	0.2330 (3)	−0.0629 (3)	0.5732 (4)	0.0707 (9)
C2	0.1387 (4)	−0.1323 (3)	0.4603 (5)	0.0946 (12)
H2	0.1646	−0.1474	0.3881	0.114*
C3	0.0032 (5)	−0.1810 (4)	0.4517 (7)	0.131 (2)
H3	−0.0605	−0.2276	0.3745	0.157*
C4	−0.0332 (6)	−0.1590 (6)	0.5575 (10)	0.141 (3)
H4	−0.1225	−0.1915	0.5525	0.169*
C5	0.0599 (6)	−0.0892 (5)	0.6724 (7)	0.1203 (18)
H5	0.0326	−0.0752	0.7439	0.144*
C6	0.1936 (4)	−0.0398 (3)	0.6825 (4)	0.0825 (11)
C7	0.2936 (5)	0.0298 (3)	0.8120 (4)	0.0916 (12)
H7A	0.2447	0.0388	0.8723	0.110*
H7B	0.3532	−0.0220	0.8374	0.110*
C8	0.3760 (3)	−0.0180 (2)	0.5746 (3)	0.0634 (8)
H8A	0.4280	−0.0669	0.6193	0.076*
H8B	0.3772	−0.0372	0.4880	0.076*
C9	0.4226 (3)	0.2080 (2)	0.5675 (2)	0.0450 (6)
C10	0.3472 (3)	0.2665 (3)	0.8592 (3)	0.0641 (8)
C11	0.4844 (3)	0.1701 (2)	0.7674 (2)	0.0576 (7)
C12	0.5931 (4)	0.1179 (3)	0.8426 (3)	0.0844 (11)
C13	0.7589 (10)	0.0161 (11)	0.8247 (10)	0.138 (4)	0.58 (13)
H13A	0.7778	−0.0399	0.7594	0.166*	0.58
H13B	0.7242	−0.0352	0.8757	0.166*	0.58
C14	0.8840 (12)	0.1122 (12)	0.9046 (13)	0.184 (6)	0.58 (13)
H14A	0.9079	0.1746	0.8599	0.276*	0.58
H14B	0.9548	0.0719	0.9253	0.276*	0.58
H14C	0.8712	0.1533	0.9809	0.276*	0.58
C15	0.5263 (3)	0.3179 (2)	0.7817 (2)	0.0504 (7)
C16	0.6759 (4)	0.3861 (3)	0.8485 (3)	0.0730 (9)
C17	0.8800 (10)	0.4862 (14)	0.8238 (14)	0.188 (5)	0.56 (12)
H17A	0.9208	0.4584	0.8974	0.225*	0.56
H17B	0.9202	0.4634	0.7588	0.225*	0.56
C18	0.8945 (16)	0.6226 (16)	0.856 (2)	0.190 (8)	0.56
H18A	0.8694	0.6505	0.7802	0.286*	0.56
H18B	0.9865	0.6674	0.9046	0.286*	0.56
H18C	0.8370	0.6399	0.9055	0.286*	0.56
C19	0.4409 (3)	0.4385 (2)	0.6278 (2)	0.0519 (7)
H19A	0.3984	0.4254	0.5377	0.062*
H19B	0.5196	0.5119	0.6559	0.062*
C20	0.4129 (3)	0.4808 (2)	0.8311 (2)	0.0569 (7)
H20A	0.4942	0.5514	0.8604	0.068*
H20B	0.3532	0.5012	0.8779	0.068*
C21	0.2878 (3)	0.5689 (3)	0.6669 (3)	0.0642 (8)
C22	0.1716 (4)	0.5641 (4)	0.7200 (4)	0.0937 (11)
H22A	0.1086	0.4808	0.6865	0.141*
H22B	0.1272	0.6267	0.6965	0.141*
H22C	0.2053	0.5818	0.8106	0.141*
C23	0.3910 (4)	0.7005 (3)	0.7234 (4)	0.0996 (12)
H23A	0.4286	0.7134	0.8132	0.149*
H23B	0.3472	0.7654	0.7068	0.149*
H23C	0.4616	0.7051	0.6857	0.149*
C24	0.2300 (4)	0.5452 (4)	0.5232 (3)	0.0966 (12)
H24A	0.3019	0.5505	0.4871	0.145*
H24B	0.1848	0.6085	0.5040	0.145*
H24C	0.1671	0.4620	0.4885	0.145*
C13'	0.8049 (12)	0.0858 (17)	0.867 (2)	0.169 (8)	0.42 (13)
H13C	0.8264	0.1281	0.9558	0.203*	0.42
H13D	0.8837	0.1142	0.8419	0.203*	0.42
C14'	0.7753 (15)	−0.0522 (15)	0.8527 (12)	0.165 (6)	0.42 (13)
H14D	0.7121	−0.0780	0.8957	0.248*	0.42
H14E	0.8571	−0.0735	0.8885	0.248*	0.42
H14F	0.7374	−0.0957	0.7645	0.248*	0.42
C17'	0.8558 (11)	0.5710 (11)	0.8799 (13)	0.095 (3)	0.44 (12)
H17C	0.9176	0.5259	0.8575	0.113*	0.44
H17D	0.8793	0.5963	0.9713	0.113*	0.44
C18'	0.8578 (12)	0.6842 (12)	0.8253 (13)	0.127 (5)	0.44 (12)
H18D	0.8380	0.6571	0.7353	0.190*	0.44
H18E	0.9454	0.7444	0.8619	0.190*	0.44
H18F	0.7913	0.7236	0.8435	0.190*	0.44
N1	0.4438 (2)	0.11805 (18)	0.63279 (19)	0.0510 (6)
N2	0.3746 (3)	0.1548 (2)	0.8183 (2)	0.0725 (8)
N3	0.4818 (2)	0.32668 (18)	0.65159 (18)	0.0479 (5)
N4	0.4467 (2)	0.3659 (2)	0.85387 (19)	0.0550 (6)
N5	0.3465 (2)	0.46257 (18)	0.69526 (18)	0.0503 (6)
O1	0.36756 (19)	0.18819 (16)	0.45526 (17)	0.0599 (5)
O2	0.2539 (3)	0.2773 (2)	0.8978 (2)	0.0899 (8)
O3	0.5872 (17)	0.0875 (14)	0.9359 (8)	0.135 (5)	0.58 (13)
O4	0.6596 (7)	0.0723 (8)	0.7670 (7)	0.098 (3)	0.58 (13)
O5	0.7302 (5)	0.3777 (6)	0.9524 (3)	0.0774 (14)	0.56 (12)
O6	0.7316 (6)	0.4306 (9)	0.7765 (6)	0.136 (3)	0.56
O3'	0.624 (2)	0.1280 (19)	0.9535 (9)	0.124 (6)	0.42 (13)
O4'	0.6965 (9)	0.1227 (10)	0.7948 (10)	0.086 (3)	0.42 (13)
O5'	0.7607 (13)	0.3412 (14)	0.893 (2)	0.259 (8)	0.44 (12)
O6'	0.7172 (6)	0.4933 (5)	0.8223 (8)	0.091 (3)	0.44 (12)

	U11	U22	U33	U12	U13	U23
C1	0.068 (2)	0.0460 (16)	0.113 (3)	0.0248 (15)	0.034 (2)	0.0346 (17)
C2	0.074 (3)	0.0547 (19)	0.145 (4)	0.0146 (18)	0.015 (3)	0.033 (2)
C3	0.086 (4)	0.074 (3)	0.220 (7)	0.019 (2)	0.015 (4)	0.060 (4)
C4	0.075 (3)	0.089 (3)	0.287 (9)	0.031 (3)	0.067 (5)	0.092 (5)
C5	0.102 (4)	0.084 (3)	0.235 (6)	0.047 (3)	0.100 (4)	0.089 (4)
C6	0.081 (2)	0.0564 (18)	0.151 (4)	0.0345 (18)	0.068 (3)	0.059 (2)
C7	0.130 (3)	0.073 (2)	0.116 (3)	0.041 (2)	0.082 (3)	0.051 (2)
C8	0.069 (2)	0.0480 (15)	0.082 (2)	0.0226 (14)	0.0330 (16)	0.0182 (14)
C9	0.0465 (15)	0.0489 (14)	0.0454 (15)	0.0169 (11)	0.0220 (12)	0.0110 (12)
C10	0.094 (2)	0.0698 (18)	0.0530 (17)	0.0396 (17)	0.0424 (17)	0.0273 (14)
C11	0.076 (2)	0.0577 (15)	0.0579 (18)	0.0337 (14)	0.0313 (15)	0.0261 (13)
C12	0.119 (3)	0.083 (2)	0.068 (2)	0.054 (2)	0.026 (2)	0.035 (2)
C13	0.142 (7)	0.122 (7)	0.149 (7)	0.104 (6)	0.001 (5)	0.015 (6)
C14	0.126 (9)	0.213 (12)	0.166 (10)	0.093 (9)	−0.029 (8)	−0.008 (8)
C15	0.0614 (18)	0.0584 (15)	0.0383 (14)	0.0277 (13)	0.0170 (13)	0.0143 (12)
C16	0.070 (2)	0.082 (2)	0.071 (2)	0.0379 (19)	0.0151 (19)	0.0211 (18)
C17	0.133 (8)	0.218 (10)	0.195 (9)	0.029 (7)	0.039 (7)	0.052 (8)
C18	0.122 (13)	0.208 (17)	0.178 (15)	0.043 (12)	−0.013 (10)	−0.010 (12)
C19	0.0669 (18)	0.0457 (13)	0.0460 (15)	0.0161 (12)	0.0200 (13)	0.0153 (11)
C20	0.0750 (19)	0.0546 (15)	0.0469 (16)	0.0286 (14)	0.0211 (14)	0.0119 (12)
C21	0.077 (2)	0.0558 (16)	0.0696 (19)	0.0343 (15)	0.0210 (16)	0.0244 (14)
C22	0.097 (3)	0.101 (3)	0.112 (3)	0.060 (2)	0.044 (2)	0.040 (2)
C23	0.121 (3)	0.0509 (18)	0.133 (3)	0.0342 (19)	0.037 (3)	0.0299 (19)
C24	0.128 (3)	0.106 (3)	0.073 (2)	0.072 (3)	0.018 (2)	0.038 (2)
C13'	0.144 (12)	0.169 (12)	0.190 (13)	0.068 (9)	0.028 (9)	0.047 (9)
C14'	0.185 (12)	0.174 (12)	0.103 (8)	0.125 (11)	−0.024 (8)	−0.029 (8)
C17'	0.053 (6)	0.077 (6)	0.121 (7)	−0.002 (4)	0.016 (5)	−0.013 (5)
C18'	0.093 (8)	0.138 (9)	0.100 (7)	−0.040 (7)	−0.001 (7)	0.043 (7)
N1	0.0648 (14)	0.0454 (11)	0.0523 (13)	0.0213 (10)	0.0270 (11)	0.0156 (10)
N2	0.108 (2)	0.0633 (14)	0.0836 (17)	0.0394 (14)	0.0650 (16)	0.0379 (13)
N3	0.0620 (14)	0.0450 (12)	0.0406 (12)	0.0193 (10)	0.0175 (10)	0.0132 (10)
N4	0.0752 (16)	0.0602 (13)	0.0400 (12)	0.0315 (12)	0.0226 (11)	0.0169 (10)
N5	0.0635 (14)	0.0456 (11)	0.0454 (12)	0.0202 (10)	0.0181 (11)	0.0133 (9)
O1	0.0706 (13)	0.0613 (11)	0.0430 (11)	0.0178 (9)	0.0145 (10)	0.0078 (9)
O2	0.122 (2)	0.0931 (16)	0.1017 (17)	0.0523 (14)	0.0815 (16)	0.0441 (13)
O3	0.172 (10)	0.171 (9)	0.107 (7)	0.076 (7)	0.047 (6)	0.111 (7)
O4	0.086 (4)	0.109 (5)	0.080 (4)	0.054 (4)	−0.009 (3)	−0.002 (3)
O5	0.072 (3)	0.115 (4)	0.0313 (19)	0.032 (3)	−0.0084 (19)	0.015 (2)
O6	0.070 (4)	0.231 (7)	0.089 (4)	−0.007 (5)	0.016 (3)	0.069 (5)
O3'	0.141 (11)	0.172 (12)	0.069 (6)	0.092 (10)	0.012 (5)	0.028 (5)
O4'	0.075 (5)	0.108 (7)	0.082 (6)	0.057 (5)	0.013 (5)	0.018 (5)
O5'	0.153 (10)	0.165 (11)	0.417 (19)	0.032 (8)	−0.001 (11)	0.124 (13)
O6'	0.054 (4)	0.059 (3)	0.137 (7)	0.008 (3)	0.012 (4)	0.008 (3)

C1—C2	1.367 (5)	C16—O6	1.243 (6)
C1—C6	1.410 (5)	C16—O6'	1.293 (6)
C1—C8	1.500 (4)	C17—C18	1.455 (17)
C2—C3	1.406 (7)	C17—O6	1.483 (10)
C2—H2	0.9300	C17—H17A	0.9700
C3—C4	1.354 (8)	C17—H17B	0.9700
C3—H3	0.9300	C18—H18A	0.9600
C4—C5	1.378 (8)	C18—H18B	0.9600
C4—H4	0.9300	C18—H18C	0.9600
C5—C6	1.385 (6)	C19—N3	1.449 (3)
C5—H5	0.9300	C19—N5	1.460 (3)
C6—C7	1.514 (5)	C19—H19A	0.9700
C7—N2	1.448 (4)	C19—H19B	0.9700
C7—H7A	0.9700	C20—N4	1.447 (3)
C7—H7B	0.9700	C20—N5	1.469 (3)
C8—N1	1.468 (3)	C20—H20A	0.9700
C8—H8A	0.9700	C20—H20B	0.9700
C8—H8B	0.9700	C21—N5	1.498 (3)
C9—O1	1.207 (3)	C21—C22	1.516 (4)
C9—N1	1.369 (3)	C21—C24	1.530 (4)
C9—N3	1.381 (3)	C21—C23	1.534 (5)
C10—O2	1.212 (3)	C22—H22A	0.9600
C10—N2	1.363 (4)	C22—H22B	0.9600
C10—N4	1.382 (4)	C22—H22C	0.9600
C11—N2	1.434 (3)	C23—H23A	0.9600
C11—N1	1.439 (3)	C23—H23B	0.9600
C11—C12	1.536 (4)	C23—H23C	0.9600
C11—C15	1.571 (4)	C24—H24A	0.9600
C12—O3	1.180 (7)	C24—H24B	0.9600
C12—O3'	1.189 (9)	C24—H24C	0.9600
C12—O4	1.350 (6)	C13'—O4'	1.418 (8)
C12—O4'	1.352 (7)	C13'—C14'	1.465 (14)
C13—O4	1.418 (7)	C13'—H13C	0.9700
C13—C14	1.463 (12)	C13'—H13D	0.9700
C13—H13A	0.9700	C14'—H14D	0.9600
C13—H13B	0.9700	C14'—H14E	0.9600
C14—H14A	0.9600	C14'—H14F	0.9600
C14—H14B	0.9600	C17'—O6'	1.450 (10)
C14—H14C	0.9600	C17'—C18'	1.497 (17)
C15—N4	1.445 (3)	C17'—H17C	0.9700
C15—N3	1.452 (3)	C17'—H17D	0.9700
C15—C16	1.529 (4)	C18'—H18D	0.9600
C16—O5'	1.170 (9)	C18'—H18E	0.9600
C16—O5	1.197 (4)	C18'—H18F	0.9600
C2—C1—C6	119.5 (3)	N3—C19—N5	109.90 (18)
C2—C1—C8	117.4 (3)	N3—C19—H19A	109.7
C6—C1—C8	123.1 (3)	N5—C19—H19A	109.7
C1—C2—C3	120.9 (5)	N3—C19—H19B	109.7
C1—C2—H2	119.5	N5—C19—H19B	109.7
C3—C2—H2	119.5	H19A—C19—H19B	108.2
C4—C3—C2	119.0 (6)	N4—C20—N5	110.0 (2)
C4—C3—H3	120.5	N4—C20—H20A	109.7
C2—C3—H3	120.5	N5—C20—H20A	109.7
C3—C4—C5	121.2 (5)	N4—C20—H20B	109.7
C3—C4—H4	119.4	N5—C20—H20B	109.7
C5—C4—H4	119.4	H20A—C20—H20B	108.2
C4—C5—C6	120.6 (5)	N5—C21—C22	107.9 (2)
C4—C5—H5	119.7	N5—C21—C24	108.7 (2)
C6—C5—H5	119.7	C22—C21—C24	107.6 (3)
C5—C6—C1	118.8 (5)	N5—C21—C23	112.8 (2)
C5—C6—C7	118.7 (4)	C22—C21—C23	109.6 (3)
C1—C6—C7	122.4 (3)	C24—C21—C23	110.1 (3)
N2—C7—C6	114.3 (3)	C21—C22—H22A	109.5
N2—C7—H7A	108.7	C21—C22—H22B	109.5
C6—C7—H7A	108.7	H22A—C22—H22B	109.5
N2—C7—H7B	108.7	C21—C22—H22C	109.5
C6—C7—H7B	108.7	H22A—C22—H22C	109.5
H7A—C7—H7B	107.6	H22B—C22—H22C	109.5
N1—C8—C1	116.0 (2)	C21—C23—H23A	109.5
N1—C8—H8A	108.3	C21—C23—H23B	109.5
C1—C8—H8A	108.3	H23A—C23—H23B	109.5
N1—C8—H8B	108.3	C21—C23—H23C	109.5
C1—C8—H8B	108.3	H23A—C23—H23C	109.5
H8A—C8—H8B	107.4	H23B—C23—H23C	109.5
O1—C9—N1	126.4 (2)	C21—C24—H24A	109.5
O1—C9—N3	125.6 (2)	C21—C24—H24B	109.5
N1—C9—N3	107.9 (2)	H24A—C24—H24B	109.5
O2—C10—N2	125.9 (3)	C21—C24—H24C	109.5
O2—C10—N4	125.6 (3)	H24A—C24—H24C	109.5
N2—C10—N4	108.5 (2)	H24B—C24—H24C	109.5
N2—C11—N1	113.7 (2)	O4'—C13'—C14'	113.2 (14)
N2—C11—C12	108.8 (2)	O4'—C13'—H13C	108.9
N1—C11—C12	113.5 (2)	C14'—C13'—H13C	108.9
N2—C11—C15	102.01 (19)	O4'—C13'—H13D	108.9
N1—C11—C15	102.94 (17)	C14'—C13'—H13D	108.9
C12—C11—C15	115.4 (3)	H13C—C13'—H13D	107.8
O3—C12—O3'	24.2 (17)	C13'—C14'—H14D	109.5
O3—C12—O4	124.6 (9)	C13'—C14'—H14E	109.5
O3'—C12—O4	124.5 (10)	H14D—C14'—H14E	109.5
O3—C12—O4'	126.2 (9)	C13'—C14'—H14F	109.5
O3'—C12—O4'	114.3 (12)	H14D—C14'—H14F	109.5
O4—C12—O4'	25.0 (6)	H14E—C14'—H14F	109.5
O3—C12—C11	121.6 (8)	O6'—C17'—C18'	103.2 (9)
O3'—C12—C11	125.3 (10)	O6'—C17'—H17C	111.1
O4—C12—C11	109.8 (4)	C18'—C17'—H17C	111.1
O4'—C12—C11	111.9 (5)	O6'—C17'—H17D	111.1
O4—C13—C14	111.9 (9)	C18'—C17'—H17D	111.1
O4—C13—H13A	109.2	H17C—C17'—H17D	109.1
C14—C13—H13A	109.2	C17'—C18'—H18D	109.5
O4—C13—H13B	109.2	C17'—C18'—H18E	109.5
C14—C13—H13B	109.2	H18D—C18'—H18E	109.5
H13A—C13—H13B	107.9	C17'—C18'—H18F	109.5
N4—C15—N3	111.76 (19)	H18D—C18'—H18F	109.5
N4—C15—C16	109.9 (2)	H18E—C18'—H18F	109.5
N3—C15—C16	112.5 (2)	C9—N1—C11	111.99 (19)
N4—C15—C11	104.0 (2)	C9—N1—C8	121.2 (2)
N3—C15—C11	102.7 (2)	C11—N1—C8	121.5 (2)
C16—C15—C11	115.6 (2)	C10—N2—C11	113.5 (2)
O5'—C16—O5	44.5 (12)	C10—N2—C7	124.6 (3)
O5'—C16—O6	95.8 (12)	C11—N2—C7	121.6 (2)
O5—C16—O6	126.7 (5)	C9—N3—C19	122.0 (2)
O5'—C16—O6'	115.4 (9)	C9—N3—C15	111.98 (19)
O5—C16—O6'	116.8 (5)	C19—N3—C15	118.26 (19)
O6—C16—O6'	39.5 (5)	C10—N4—C15	110.4 (2)
O5'—C16—C15	127.3 (8)	C10—N4—C20	118.8 (2)
O5—C16—C15	120.3 (4)	C15—N4—C20	115.72 (19)
O6—C16—C15	112.1 (4)	C19—N5—C20	108.5 (2)
O6'—C16—C15	114.4 (4)	C19—N5—C21	114.05 (19)
C18—C17—O6	102.7 (10)	C20—N5—C21	112.94 (19)
C18—C17—H17A	111.2	C12—O4—C13	115.0 (7)
O6—C17—H17A	111.2	C16—O6—C17	118.2 (7)
C18—C17—H17B	111.2	C12—O4'—C13'	114.1 (9)
O6—C17—H17B	111.2	C16—O6'—C17'	121.3 (7)
H17A—C17—H17B	109.1
C6—C1—C2—C3	−0.1 (4)	N4—C10—N2—C7	179.1 (3)
C8—C1—C2—C3	178.2 (3)	N1—C11—N2—C10	−110.4 (3)
C1—C2—C3—C4	−0.4 (6)	C12—C11—N2—C10	122.1 (3)
C2—C3—C4—C5	0.5 (7)	C15—C11—N2—C10	−0.3 (3)
C3—C4—C5—C6	0.0 (6)	N1—C11—N2—C7	63.1 (3)
C4—C5—C6—C1	−0.5 (5)	C12—C11—N2—C7	−64.4 (4)
C4—C5—C6—C7	−176.6 (3)	C15—C11—N2—C7	173.2 (3)
C2—C1—C6—C5	0.5 (4)	C6—C7—N2—C10	97.0 (4)
C8—C1—C6—C5	−177.6 (3)	C6—C7—N2—C11	−75.7 (4)
C2—C1—C6—C7	176.5 (3)	O1—C9—N3—C19	25.1 (4)
C8—C1—C6—C7	−1.7 (4)	N1—C9—N3—C19	−158.1 (2)
C5—C6—C7—N2	−128.4 (3)	O1—C9—N3—C15	173.8 (2)
C1—C6—C7—N2	55.6 (4)	N1—C9—N3—C15	−9.4 (3)
C2—C1—C8—N1	129.5 (3)	N5—C19—N3—C9	98.0 (2)
C6—C1—C8—N1	−52.3 (3)	N5—C19—N3—C15	−48.9 (3)
N2—C11—C12—O3	−8.9 (10)	N4—C15—N3—C9	−111.2 (2)
N1—C11—C12—O3	−136.5 (9)	C16—C15—N3—C9	124.6 (2)
C15—C11—C12—O3	105.0 (10)	C11—C15—N3—C9	−0.3 (3)
N2—C11—C12—O3'	−37.6 (14)	N4—C15—N3—C19	38.8 (3)
N1—C11—C12—O3'	−165.2 (14)	C16—C15—N3—C19	−85.3 (3)
C15—C11—C12—O3'	76.3 (14)	C11—C15—N3—C19	149.8 (2)
N2—C11—C12—O4	149.7 (5)	O2—C10—N4—C15	−169.4 (3)
N1—C11—C12—O4	22.0 (5)	N2—C10—N4—C15	12.9 (3)
C15—C11—C12—O4	−96.4 (5)	O2—C10—N4—C20	−32.3 (4)
N2—C11—C12—O4'	176.4 (6)	N2—C10—N4—C20	150.0 (2)
N1—C11—C12—O4'	48.7 (6)	N3—C15—N4—C10	97.5 (2)
C15—C11—C12—O4'	−69.7 (6)	C16—C15—N4—C10	−136.9 (2)
N2—C11—C15—N4	7.6 (3)	C11—C15—N4—C10	−12.6 (3)
N1—C11—C15—N4	125.7 (2)	N3—C15—N4—C20	−41.0 (3)
C12—C11—C15—N4	−110.1 (3)	C16—C15—N4—C20	84.6 (3)
N2—C11—C15—N3	−109.0 (2)	C11—C15—N4—C20	−151.1 (2)
N1—C11—C15—N3	9.1 (2)	N5—C20—N4—C10	−80.5 (3)
C12—C11—C15—N3	133.2 (2)	N5—C20—N4—C15	54.3 (3)
N2—C11—C15—C16	128.1 (2)	N3—C19—N5—C20	58.7 (3)
N1—C11—C15—C16	−113.8 (2)	N3—C19—N5—C21	−174.4 (2)
C12—C11—C15—C16	10.4 (3)	N4—C20—N5—C19	−62.2 (3)
N4—C15—C16—O5'	115.1 (16)	N4—C20—N5—C21	170.3 (2)
N3—C15—C16—O5'	−119.8 (16)	C22—C21—N5—C19	168.0 (3)
C11—C15—C16—O5'	−2.3 (16)	C24—C21—N5—C19	51.7 (3)
N4—C15—C16—O5	61.5 (4)	C23—C21—N5—C19	−70.7 (3)
N3—C15—C16—O5	−173.3 (4)	C22—C21—N5—C20	−67.4 (3)
C11—C15—C16—O5	−55.8 (5)	C24—C21—N5—C20	176.2 (2)
N4—C15—C16—O6	−128.4 (6)	C23—C21—N5—C20	53.8 (3)
N3—C15—C16—O6	−3.2 (6)	O3—C12—O4—C13	−19.6 (14)
C11—C15—C16—O6	114.3 (6)	O3'—C12—O4—C13	9.9 (17)
N4—C15—C16—O6'	−85.3 (5)	O4'—C12—O4—C13	83.1 (19)
N3—C15—C16—O6'	39.9 (5)	C11—C12—O4—C13	−177.3 (7)
C11—C15—C16—O6'	157.4 (5)	C14—C13—O4—C12	−79.4 (12)
O1—C9—N1—C11	−167.1 (2)	O5'—C16—O6—C17	−38.6 (14)
N3—C9—N1—C11	16.2 (3)	O5—C16—O6—C17	−3.6 (13)
O1—C9—N1—C8	−12.6 (4)	O6'—C16—O6—C17	85.1 (10)
N3—C9—N1—C8	170.6 (2)	C15—C16—O6—C17	−173.0 (8)
N2—C11—N1—C9	93.9 (2)	C18—C17—O6—C16	−101.4 (14)
C12—C11—N1—C9	−141.1 (3)	O3—C12—O4'—C13'	0.4 (17)
C15—C11—N1—C9	−15.6 (3)	O3'—C12—O4'—C13'	24.9 (17)
N2—C11—N1—C8	−60.5 (3)	O4—C12—O4'—C13'	−95 (2)
C12—C11—N1—C8	64.5 (3)	C11—C12—O4'—C13'	174.9 (10)
C15—C11—N1—C8	−170.0 (2)	C14'—C13'—O4'—C12	74.8 (19)
C1—C8—N1—C9	−80.3 (3)	O5'—C16—O6'—C17'	−19.1 (18)
C1—C8—N1—C11	71.8 (3)	O5—C16—O6'—C17'	30.7 (11)
O2—C10—N2—C11	174.7 (3)	O6—C16—O6'—C17'	−85.5 (10)
N4—C10—N2—C11	−7.6 (3)	C15—C16—O6'—C17'	178.8 (8)
O2—C10—N2—C7	1.4 (5)	C18'—C17'—O6'—C16	−179.2 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22C···O5i	0.96	2.52	3.474 (5)	174
C13—H13A···O1ii	0.97	2.54	3.288 (11)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22C⋯O5i	0.96	2.52	3.474 (5)	174
C13—H13A⋯O1ii	0.97	2.54	3.288 (11)	134

Symmetry codes: (i) ; (ii) .