Diethyl 2-tert-butyl-6,9-dibromo-4,11-dioxo-5,10-dihydro-cis-1H,3H,4H,11H-2-azo-3a,4a,10a,11a-tetra-aza-benz[f]indeno[2,1,7-ija]azulene-11b,11c-dicarboxyl-ate.

In the title compound, C(24)H(29)Br(2)N(5)O(6), a glycoluril derivative, the 1,4-dibromo-benzene ring is fused to the seven-membered ring of the glycoluril unit containing two N atoms. The two five-membered rings in the glycoluril unit are approximately planar and the dihedral angle between them is 69.8 (2)°. The six-membered ring containing three N atoms adopts a chair conformation. The crystal packing is stabilized by an inter-molecular non-classical C-H⋯O hydrogen bond and a weak C-H⋯π inter-action. Both of the ester groups are found to be disordered over two positions. The occupancies of the disordered positions were refined to 0.73(1):0.27(1) and 0.56(1):0.44(1).

Related literature

For the preparation of the title compound, see: Lai & Yap (1993 ▶); Li et al. (2006 ▶). For potential applications of the title compound, see: Wu et al. (2002 ▶); Rowan et al. (1999 ▶); Chakraborty et al. (2002 ▶); Lehn (1995 ▶); Diederich (1991 ▶); Purse & Rebek (2005 ▶); Yin et al. (2006 ▶). For the crystal structures of similar compounds, see: Chen et al. (2007 ▶); Wang et al. (2006 ▶).

Experimental

Crystal data

C24H29Br2N5O6

M = 643.34

Monoclinic,

a = 10.4151 (8) Å

b = 11.3801 (8) Å

c = 23.1649 (17) Å

β = 92.692 (1)°

V = 2742.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 3.00 mm−1

T = 293 (2) K

0.10 × 0.06 × 0.04 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: none

18064 measured reflections

4828 independent reflections

2185 reflections with I > 2σ(I)

R int = 0.120

Refinement

R[F 2 > 2σ(F 2)] = 0.080

wR(F 2) = 0.232

S = 0.88

4828 reflections

415 parameters

22 restraints

H-atom parameters constrained

Δρmax = 1.91 e Å−3

Δρmin = −0.53 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; 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: PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807062472/is2227sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062472/is2227Isup2.hkl

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

C24H29Br2N5O6	F000 = 1304
Mr = 643.34	Dx = 1.558 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2626 reflections
a = 10.4151 (8) Å	θ = 2.2–18.8º
b = 11.3801 (8) Å	µ = 3.00 mm−1
c = 23.1649 (17) Å	T = 293 (2) K
β = 92.692 (1)º	Block, blue
V = 2742.6 (3) Å3	0.10 × 0.06 × 0.04 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2185 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.120
Monochromator: graphite	θmax = 25.0º
T = 293(2) K	θmin = 1.8º
φ and ω scans	h = −12→12
Absorption correction: none	k = −13→11
18064 measured reflections	l = −27→25
4828 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)] = 0.080	H-atom parameters constrained
wR(F2) = 0.232	w = 1/[σ2(Fo2) + (0.1377P)2] where P = (Fo2 + 2Fc2)/3
S = 0.88	(Δ/σ)max < 0.001
4828 reflections	Δρmax = 1.91 e Å−3
415 parameters	Δρmin = −0.53 e Å−3
22 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)
Br1	0.87255 (10)	1.26953 (9)	0.14865 (5)	0.0940 (5)
Br2	1.27715 (11)	0.96144 (11)	0.00489 (5)	0.1022 (5)
C1	1.0559 (7)	1.0823 (7)	0.1398 (3)	0.0510 (19)
C2	1.1426 (7)	1.0152 (7)	0.1078 (4)	0.056 (2)
C3	1.1591 (8)	1.0401 (8)	0.0494 (4)	0.070 (3)
C4	1.0897 (10)	1.1305 (9)	0.0219 (4)	0.077 (3)
H4	1.1011	1.1472	−0.0168	0.093*
C5	1.0050 (9)	1.1941 (8)	0.0523 (5)	0.078 (3)
H5	0.9577	1.2537	0.0338	0.093*
C6	0.9880 (7)	1.1713 (7)	0.1106 (4)	0.062 (2)
C7	1.0491 (7)	1.0630 (6)	0.2031 (3)	0.0517 (19)
H7A	1.1346	1.0725	0.2209	0.062*
H7B	0.9948	1.1234	0.2187	0.062*
C8	1.2156 (7)	0.9152 (8)	0.1365 (4)	0.063 (2)
H8A	1.2672	0.8770	0.1082	0.075*
H8B	1.2738	0.9466	0.1666	0.075*
C9	0.8717 (7)	0.9214 (6)	0.2150 (3)	0.0457 (18)
C10	1.0663 (7)	0.7450 (6)	0.1288 (4)	0.051 (2)
C11	1.0791 (7)	0.8450 (6)	0.2169 (3)	0.0475 (18)
C12	1.1894 (8)	0.8394 (8)	0.2628 (4)	0.068 (2)
C13	1.2920 (14)	0.9101 (19)	0.3468 (8)	0.074 (5)	0.73 (3)
H13A	1.3671	0.9391	0.3280	0.089*	0.73 (3)
H13B	1.3097	0.8309	0.3605	0.089*	0.73 (3)
C14	1.261 (2)	0.991 (2)	0.3979 (8)	0.107 (8)	0.73 (3)
H14A	1.2380	1.0674	0.3835	0.160*	0.73 (3)
H14B	1.3347	0.9965	0.4241	0.160*	0.73 (3)
H14C	1.1901	0.9582	0.4177	0.160*	0.73 (3)
O3	1.2862 (18)	0.7808 (19)	0.2575 (12)	0.124 (8)	0.73 (3)
O4	1.1805 (17)	0.9107 (18)	0.3066 (7)	0.066 (6)	0.73 (3)
C13'	1.281 (4)	0.976 (5)	0.3379 (12)	0.065 (13)	0.27 (3)
H13C	1.2783	1.0614	0.3412	0.077*	0.27 (3)
H13D	1.3659	0.9549	0.3254	0.077*	0.27 (3)
C14'	1.260 (4)	0.921 (4)	0.3968 (16)	0.061 (13)	0.27 (3)
H14D	1.2240	0.8438	0.3914	0.092*	0.27 (3)
H14E	1.2020	0.9689	0.4176	0.092*	0.27 (3)
H14F	1.3407	0.9152	0.4185	0.092*	0.27 (3)
O3'	1.240 (4)	0.745 (2)	0.274 (2)	0.070 (11)	0.27 (3)
O4'	1.185 (6)	0.938 (3)	0.2953 (17)	0.067 (16)	0.27 (3)
C15	0.9798 (7)	0.7420 (6)	0.2205 (3)	0.0448 (18)
C16	1.0060 (8)	0.6547 (6)	0.2707 (3)	0.058 (2)
C19	0.7462 (7)	0.7404 (7)	0.2009 (3)	0.054 (2)
H19A	0.6720	0.7920	0.2010	0.065*
H19B	0.7292	0.6727	0.2248	0.065*
C20	0.8754 (7)	0.6202 (7)	0.1429 (3)	0.058 (2)
H20A	0.8892	0.5907	0.1044	0.070*
H20B	0.8573	0.5539	0.1676	0.070*
C21	0.6505 (8)	0.6557 (8)	0.1086 (4)	0.070 (2)
C22	0.5477 (10)	0.7499 (11)	0.1080 (6)	0.124 (5)
H22A	0.5338	0.7744	0.1468	0.186*
H22B	0.4691	0.7190	0.0907	0.186*
H22C	0.5749	0.8160	0.0859	0.186*
C23	0.6001 (10)	0.5414 (9)	0.1369 (5)	0.106 (4)
H23A	0.6650	0.4816	0.1361	0.159*
H23B	0.5241	0.5149	0.1157	0.159*
H23C	0.5802	0.5572	0.1762	0.159*
C24	0.6860 (12)	0.6247 (13)	0.0476 (4)	0.127 (5)
H24A	0.7421	0.6840	0.0334	0.191*
H24B	0.6094	0.6206	0.0229	0.191*
H24C	0.7288	0.5500	0.0478	0.191*
N1	0.9991 (5)	0.9471 (5)	0.2194 (2)	0.0448 (14)
N2	0.8576 (5)	0.8014 (5)	0.2239 (3)	0.0495 (15)
N3	0.9906 (6)	0.6825 (5)	0.1656 (2)	0.0486 (15)
N4	1.1327 (5)	0.8276 (5)	0.1619 (3)	0.0484 (15)
N5	0.7677 (6)	0.7018 (5)	0.1411 (3)	0.0511 (16)
O1	0.7850 (5)	0.9907 (4)	0.2079 (2)	0.0591 (14)
O2	1.0786 (6)	0.7265 (5)	0.0781 (3)	0.0711 (16)
O5	1.030 (3)	0.5476 (9)	0.2619 (7)	0.064 (5)	0.57 (4)
O6	0.986 (2)	0.7074 (12)	0.3223 (4)	0.042 (4)	0.57 (4)
C17	1.006 (4)	0.641 (2)	0.3743 (5)	0.070 (8)	0.57 (4)
H17A	1.0955	0.6186	0.3793	0.084*	0.57 (4)
H17B	0.9547	0.5695	0.3717	0.084*	0.57 (4)
C18	0.967 (5)	0.714 (4)	0.4262 (7)	0.134 (19)	0.57 (4)
H18A	1.0018	0.7915	0.4235	0.201*	0.57 (4)
H18B	0.9995	0.6772	0.4612	0.201*	0.57 (4)
H18C	0.8748	0.7181	0.4264	0.201*	0.57 (4)
O6'	0.937 (2)	0.689 (2)	0.3156 (8)	0.044 (6)	0.43 (4)
O5'	1.095 (3)	0.581 (3)	0.2663 (10)	0.086 (9)	0.43 (4)
C17'	0.963 (4)	0.622 (3)	0.3649 (11)	0.059 (11)	0.43 (4)
H17C	1.0296	0.5654	0.3572	0.071*	0.43 (4)
H17D	0.8861	0.5783	0.3739	0.071*	0.43 (4)
C18'	1.006 (4)	0.697 (3)	0.4175 (12)	0.058 (9)	0.43 (4)
H18D	1.0815	0.7407	0.4088	0.086*	0.43 (4)
H18E	1.0249	0.6468	0.4501	0.086*	0.43 (4)
H18F	0.9384	0.7505	0.4264	0.086*	0.43 (4)

	U11	U22	U33	U12	U13	U23
Br1	0.0846 (8)	0.0613 (6)	0.1359 (11)	0.0207 (5)	0.0027 (6)	0.0263 (6)
Br2	0.1050 (9)	0.1171 (10)	0.0874 (8)	−0.0272 (7)	0.0366 (6)	−0.0131 (6)
C1	0.044 (4)	0.050 (5)	0.058 (5)	−0.010 (4)	−0.004 (4)	0.004 (4)
C2	0.048 (4)	0.055 (5)	0.063 (6)	−0.018 (4)	−0.005 (4)	0.007 (4)
C3	0.068 (6)	0.078 (6)	0.063 (6)	−0.042 (5)	−0.012 (5)	0.015 (5)
C4	0.098 (8)	0.079 (7)	0.054 (6)	−0.016 (6)	−0.008 (5)	0.017 (5)
C5	0.080 (7)	0.055 (6)	0.095 (8)	−0.016 (5)	−0.037 (6)	0.029 (6)
C6	0.057 (5)	0.056 (5)	0.073 (6)	−0.007 (4)	−0.014 (4)	0.016 (5)
C7	0.052 (5)	0.038 (4)	0.065 (5)	−0.004 (3)	−0.006 (4)	−0.001 (4)
C8	0.046 (5)	0.077 (6)	0.066 (5)	0.001 (4)	0.010 (4)	0.009 (5)
C9	0.052 (5)	0.040 (5)	0.044 (5)	0.008 (4)	−0.003 (4)	0.003 (3)
C10	0.055 (5)	0.041 (5)	0.055 (6)	0.014 (4)	−0.002 (4)	0.000 (4)
C11	0.051 (4)	0.038 (4)	0.053 (5)	0.001 (3)	−0.012 (4)	0.004 (4)
C12	0.058 (6)	0.067 (7)	0.078 (8)	0.006 (5)	−0.026 (5)	0.007 (6)
C13	0.066 (9)	0.087 (13)	0.066 (12)	0.006 (9)	−0.021 (8)	0.019 (11)
C14	0.112 (14)	0.102 (18)	0.104 (17)	−0.035 (15)	−0.031 (11)	−0.003 (13)
O3	0.094 (12)	0.121 (13)	0.15 (2)	0.043 (11)	−0.054 (11)	−0.037 (11)
O4	0.056 (9)	0.090 (9)	0.050 (7)	−0.002 (8)	−0.023 (7)	0.001 (9)
C13'	0.07 (2)	0.06 (3)	0.07 (3)	0.00 (2)	0.00 (2)	0.00 (2)
C14'	0.06 (2)	0.07 (3)	0.05 (3)	0.00 (2)	−0.001 (18)	−0.01 (2)
O3'	0.06 (2)	0.07 (2)	0.08 (2)	0.010 (16)	−0.020 (16)	0.016 (15)
O4'	0.06 (2)	0.08 (3)	0.06 (3)	−0.022 (17)	0.009 (16)	0.01 (2)
C15	0.057 (5)	0.033 (4)	0.044 (4)	0.005 (3)	−0.005 (4)	0.006 (3)
C16	0.071 (6)	0.064 (6)	0.037 (5)	0.012 (5)	−0.014 (4)	0.015 (4)
C19	0.050 (5)	0.053 (5)	0.061 (5)	0.000 (4)	0.006 (4)	0.004 (4)
C20	0.078 (6)	0.051 (5)	0.046 (5)	−0.005 (4)	0.001 (4)	−0.003 (4)
C21	0.076 (6)	0.071 (6)	0.062 (6)	−0.019 (5)	−0.013 (5)	0.008 (5)
C22	0.089 (8)	0.112 (9)	0.163 (12)	0.003 (7)	−0.075 (8)	0.024 (8)
C23	0.097 (8)	0.103 (8)	0.115 (8)	−0.063 (6)	−0.026 (6)	0.012 (7)
C24	0.130 (10)	0.180 (13)	0.069 (8)	−0.028 (9)	−0.025 (7)	−0.005 (8)
N1	0.043 (4)	0.041 (4)	0.049 (4)	0.007 (3)	−0.005 (3)	0.002 (3)
N2	0.041 (3)	0.053 (4)	0.054 (4)	0.003 (3)	−0.003 (3)	0.002 (3)
N3	0.065 (4)	0.043 (3)	0.039 (3)	0.000 (3)	0.001 (3)	0.004 (3)
N4	0.048 (4)	0.048 (4)	0.050 (4)	0.004 (3)	0.006 (3)	−0.004 (3)
N5	0.056 (4)	0.038 (4)	0.058 (4)	−0.002 (3)	−0.009 (3)	0.007 (3)
O1	0.054 (3)	0.041 (3)	0.082 (4)	0.018 (3)	−0.006 (3)	0.004 (3)
O2	0.086 (4)	0.081 (4)	0.047 (4)	0.016 (3)	0.011 (3)	0.002 (3)
O5	0.082 (13)	0.040 (7)	0.070 (8)	0.018 (6)	0.008 (8)	0.017 (6)
O6	0.035 (9)	0.050 (7)	0.040 (7)	−0.003 (6)	−0.011 (5)	0.009 (5)
C17	0.08 (2)	0.071 (16)	0.058 (16)	0.005 (14)	−0.015 (12)	0.016 (14)
C18	0.14 (4)	0.17 (4)	0.09 (2)	0.02 (2)	0.013 (19)	0.03 (2)
O6'	0.042 (11)	0.054 (10)	0.034 (9)	−0.006 (9)	−0.020 (8)	0.013 (7)
O5'	0.096 (17)	0.089 (16)	0.073 (12)	0.027 (16)	−0.017 (13)	0.027 (11)
C17'	0.07 (2)	0.058 (16)	0.054 (17)	−0.017 (14)	−0.011 (13)	0.004 (13)
C18'	0.058 (17)	0.058 (17)	0.06 (2)	0.000 (13)	0.003 (13)	0.000 (15)

Br1—C6	1.890 (9)	C14'—H14E	0.9600
Br2—C3	1.869 (10)	C14'—H14F	0.9600
C1—C6	1.392 (11)	C15—N2	1.446 (9)
C1—C2	1.418 (11)	C15—N3	1.451 (9)
C1—C7	1.488 (10)	C15—C16	1.544 (9)
C2—C3	1.402 (11)	C16—O5'	1.260 (8)
C2—C8	1.505 (11)	C16—O5	1.263 (8)
C3—C4	1.394 (13)	C16—O6'	1.350 (9)
C4—C5	1.362 (13)	C16—O6	1.361 (8)
C4—H4	0.9300	C19—N2	1.434 (9)
C5—C6	1.395 (13)	C19—N5	1.480 (9)
C5—H5	0.9300	C19—H19A	0.9700
C7—N1	1.475 (9)	C19—H19B	0.9700
C7—H7A	0.9700	C20—N5	1.455 (9)
C7—H7B	0.9700	C20—N3	1.470 (9)
C8—N4	1.460 (9)	C20—H20A	0.9700
C8—H8A	0.9700	C20—H20B	0.9700
C8—H8B	0.9700	C21—N5	1.498 (10)
C9—O1	1.204 (8)	C21—C22	1.515 (14)
C9—N1	1.358 (9)	C21—C24	1.520 (13)
C9—N2	1.391 (9)	C21—C23	1.559 (12)
C10—O2	1.205 (9)	C22—H22A	0.9600
C10—N4	1.378 (9)	C22—H22B	0.9600
C10—N3	1.385 (10)	C22—H22C	0.9600
C11—N4	1.429 (9)	C23—H23A	0.9600
C11—N1	1.432 (8)	C23—H23B	0.9600
C11—C12	1.530 (11)	C23—H23C	0.9600
C11—C15	1.569 (10)	C24—H24A	0.9600
C12—O3'	1.219 (14)	C24—H24B	0.9600
C12—O3	1.220 (12)	C24—H24C	0.9600
C12—O4	1.305 (9)	O6—C17	1.429 (9)
C12—O4'	1.352 (11)	C17—C18	1.531 (10)
C13—O4	1.455 (10)	C17—H17A	0.9700
C13—C14	1.542 (10)	C17—H17B	0.9700
C13—H13A	0.9700	C18—H18A	0.9600
C13—H13B	0.9700	C18—H18B	0.9600
C14—H14A	0.9600	C18—H18C	0.9600
C14—H14B	0.9600	O6'—C17'	1.389 (10)
C14—H14C	0.9600	C17'—C18'	1.540 (10)
C13'—O4'	1.44 (5)	C17'—H17C	0.9700
C13'—C14'	1.531 (11)	C17'—H17D	0.9700
C13'—H13C	0.9700	C18'—H18D	0.9600
C13'—H13D	0.9700	C18'—H18E	0.9600
C14'—H14D	0.9600	C18'—H18F	0.9600
C6—C1—C2	117.4 (7)	O5'—C16—C15	118.2 (13)
C6—C1—C7	122.6 (7)	O5—C16—C15	121.9 (9)
C2—C1—C7	119.7 (7)	O6'—C16—C15	108.2 (10)
C3—C2—C1	120.3 (8)	O6—C16—C15	110.4 (8)
C3—C2—C8	119.8 (8)	N2—C19—N5	109.6 (6)
C1—C2—C8	119.9 (7)	N2—C19—H19A	109.7
C4—C3—C2	120.4 (9)	N5—C19—H19A	109.7
C4—C3—Br2	116.2 (7)	N2—C19—H19B	109.7
C2—C3—Br2	123.3 (7)	N5—C19—H19B	109.7
C5—C4—C3	119.4 (9)	H19A—C19—H19B	108.2
C5—C4—H4	120.3	N5—C20—N3	108.5 (6)
C3—C4—H4	120.3	N5—C20—H20A	110.0
C4—C5—C6	121.0 (8)	N3—C20—H20A	110.0
C4—C5—H5	119.5	N5—C20—H20B	110.0
C6—C5—H5	119.5	N3—C20—H20B	110.0
C1—C6—C5	121.4 (8)	H20A—C20—H20B	108.4
C1—C6—Br1	121.6 (7)	N5—C21—C22	108.5 (8)
C5—C6—Br1	117.0 (7)	N5—C21—C24	108.7 (7)
N1—C7—C1	114.8 (6)	C22—C21—C24	110.9 (9)
N1—C7—H7A	108.6	N5—C21—C23	111.4 (7)
C1—C7—H7A	108.6	C22—C21—C23	110.1 (9)
N1—C7—H7B	108.6	C24—C21—C23	107.3 (9)
C1—C7—H7B	108.6	C21—C22—H22A	109.5
H7A—C7—H7B	107.6	C21—C22—H22B	109.5
N4—C8—C2	113.4 (6)	H22A—C22—H22B	109.5
N4—C8—H8A	108.9	C21—C22—H22C	109.5
C2—C8—H8A	108.9	H22A—C22—H22C	109.5
N4—C8—H8B	108.9	H22B—C22—H22C	109.5
C2—C8—H8B	108.9	C21—C23—H23A	109.5
H8A—C8—H8B	107.7	C21—C23—H23B	109.5
O1—C9—N1	126.4 (7)	H23A—C23—H23B	109.5
O1—C9—N2	125.5 (7)	C21—C23—H23C	109.5
N1—C9—N2	108.0 (6)	H23A—C23—H23C	109.5
O2—C10—N4	126.0 (8)	H23B—C23—H23C	109.5
O2—C10—N3	126.8 (7)	C21—C24—H24A	109.5
N4—C10—N3	107.1 (7)	C21—C24—H24B	109.5
N4—C11—N1	113.7 (6)	H24A—C24—H24B	109.5
N4—C11—C12	107.6 (6)	C21—C24—H24C	109.5
N1—C11—C12	115.1 (6)	H24A—C24—H24C	109.5
N4—C11—C15	103.3 (6)	H24B—C24—H24C	109.5
N1—C11—C15	102.6 (5)	C9—N1—C11	113.0 (6)
C12—C11—C15	114.0 (6)	C9—N1—C7	121.9 (6)
O3—C12—O4	120.5 (14)	C11—N1—C7	120.1 (6)
O3'—C12—O4'	130 (3)	C9—N2—C19	120.6 (6)
O3'—C12—C11	119 (3)	C9—N2—C15	110.6 (6)
O3—C12—C11	123.4 (13)	C19—N2—C15	116.9 (6)
O4—C12—C11	115.8 (9)	C10—N3—C15	111.7 (6)
O4'—C12—C11	107.9 (19)	C10—N3—C20	120.4 (6)
O4—C13—C14	107.3 (9)	C15—N3—C20	116.3 (6)
O4—C13—H13A	110.3	C10—N4—C11	112.6 (6)
C14—C13—H13A	110.3	C10—N4—C8	122.2 (7)
O4—C13—H13B	110.3	C11—N4—C8	121.8 (6)
C14—C13—H13B	110.3	C20—N5—C19	108.3 (6)
H13A—C13—H13B	108.5	C20—N5—C21	113.5 (6)
C12—O4—C13	114.3 (12)	C19—N5—C21	114.7 (6)
O4'—C13'—C14'	111 (3)	C16—O6—C17	119.0 (10)
O4'—C13'—H13C	109.5	O6—C17—C18	110.0 (10)
C14'—C13'—H13C	109.5	O6—C17—H17A	109.7
O4'—C13'—H13D	109.5	C18—C17—H17A	109.7
C14'—C13'—H13D	109.5	O6—C17—H17B	109.7
H13C—C13'—H13D	108.0	C18—C17—H17B	109.7
C13'—C14'—H14D	109.5	H17A—C17—H17B	108.2
C13'—C14'—H14E	109.5	C16—O6'—C17'	112.5 (19)
H14D—C14'—H14E	109.5	O6'—C17'—C18'	112.5 (11)
C13'—C14'—H14F	109.5	O6'—C17'—H17C	109.1
H14D—C14'—H14F	109.5	C18'—C17'—H17C	109.1
H14E—C14'—H14F	109.5	O6'—C17'—H17D	109.1
C12—O4'—C13'	126 (4)	C18'—C17'—H17D	109.1
N2—C15—N3	111.7 (6)	H17C—C17'—H17D	107.8
N2—C15—C16	112.6 (6)	C17'—C18'—H18D	109.5
N3—C15—C16	110.0 (5)	C17'—C18'—H18E	109.5
N2—C15—C11	103.7 (5)	H18D—C18'—H18E	109.5
N3—C15—C11	102.9 (5)	C17'—C18'—H18F	109.5
C16—C15—C11	115.4 (6)	H18D—C18'—H18F	109.5
O5'—C16—O6'	132.6 (12)	H18E—C18'—H18F	109.5
O5—C16—O6	127.4 (9)
C6—C1—C2—C3	0.8 (10)	O1—C9—N1—C7	−14.0 (11)
C7—C1—C2—C3	−173.8 (6)	N2—C9—N1—C7	169.9 (6)
C6—C1—C2—C8	−178.1 (7)	N4—C11—N1—C9	101.4 (7)
C7—C1—C2—C8	7.4 (10)	C12—C11—N1—C9	−133.8 (7)
C1—C2—C3—C4	−0.5 (11)	C15—C11—N1—C9	−9.5 (7)
C8—C2—C3—C4	178.4 (7)	N4—C11—N1—C7	−54.1 (8)
C1—C2—C3—Br2	176.8 (5)	C12—C11—N1—C7	70.7 (9)
C8—C2—C3—Br2	−4.3 (10)	C15—C11—N1—C7	−165.0 (6)
C2—C3—C4—C5	−0.4 (13)	C1—C7—N1—C9	−77.0 (8)
Br2—C3—C4—C5	−177.9 (7)	C1—C7—N1—C11	76.3 (8)
C3—C4—C5—C6	0.9 (13)	O1—C9—N2—C19	28.2 (11)
C2—C1—C6—C5	−0.3 (11)	N1—C9—N2—C19	−155.8 (6)
C7—C1—C6—C5	174.1 (7)	O1—C9—N2—C15	169.9 (7)
C2—C1—C6—Br1	−178.4 (5)	N1—C9—N2—C15	−14.1 (8)
C7—C1—C6—Br1	−4.0 (10)	N5—C19—N2—C9	87.2 (8)
C4—C5—C6—C1	−0.6 (13)	N5—C19—N2—C15	−52.3 (8)
C4—C5—C6—Br1	177.7 (7)	N3—C15—N2—C9	−102.2 (7)
C6—C1—C7—N1	119.2 (7)	C16—C15—N2—C9	133.3 (6)
C2—C1—C7—N1	−66.5 (9)	C11—C15—N2—C9	7.9 (7)
C3—C2—C8—N4	−122.8 (7)	N3—C15—N2—C19	41.0 (8)
C1—C2—C8—N4	56.1 (10)	C16—C15—N2—C19	−83.5 (8)
N4—C11—C12—O3'	−71 (2)	C11—C15—N2—C19	151.1 (6)
N1—C11—C12—O3'	161 (2)	O2—C10—N3—C15	−169.2 (7)
C15—C11—C12—O3'	43 (3)	N4—C10—N3—C15	15.2 (8)
N4—C11—C12—O3	−30 (2)	O2—C10—N3—C20	−27.3 (11)
N1—C11—C12—O3	−157.6 (19)	N4—C10—N3—C20	157.1 (6)
C15—C11—C12—O3	84 (2)	N2—C15—N3—C10	102.2 (7)
N4—C11—C12—O4	143.8 (16)	C16—C15—N3—C10	−131.8 (6)
N1—C11—C12—O4	15.8 (18)	C11—C15—N3—C10	−8.4 (7)
C15—C11—C12—O4	−102.3 (16)	N2—C15—N3—C20	−41.4 (8)
N4—C11—C12—O4'	127 (3)	C16—C15—N3—C20	84.5 (8)
N1—C11—C12—O4'	−1(3)	C11—C15—N3—C20	−152.0 (6)
C15—C11—C12—O4'	−119 (3)	N5—C20—N3—C10	−86.7 (8)
O3'—C12—O4—C13	39 (3)	N5—C20—N3—C15	53.6 (8)
O3—C12—O4—C13	−1(3)	O2—C10—N4—C11	168.1 (7)
O4'—C12—O4—C13	−109 (11)	N3—C10—N4—C11	−16.2 (8)
C11—C12—O4—C13	−175.0 (15)	O2—C10—N4—C8	8.7 (11)
C14—C13—O4—C12	−175 (3)	N3—C10—N4—C8	−175.7 (6)
O3'—C12—O4'—C13'	30 (8)	N1—C11—N4—C10	−99.8 (7)
O3—C12—O4'—C13'	−14 (7)	C12—C11—N4—C10	131.5 (6)
O4—C12—O4'—C13'	70 (7)	C15—C11—N4—C10	10.6 (7)
C11—C12—O4'—C13'	−170 (4)	N1—C11—N4—C8	59.7 (8)
C14'—C13'—O4'—C12	−87 (8)	C12—C11—N4—C8	−69.0 (8)
N4—C11—C15—N2	−117.7 (6)	C15—C11—N4—C8	170.1 (6)
N1—C11—C15—N2	0.7 (7)	C2—C8—N4—C10	77.2 (9)
C12—C11—C15—N2	125.8 (7)	C2—C8—N4—C11	−80.3 (9)
N4—C11—C15—N3	−1.2 (6)	N3—C20—N5—C19	−62.2 (7)
N1—C11—C15—N3	117.2 (6)	N3—C20—N5—C21	169.2 (6)
C12—C11—C15—N3	−117.6 (7)	N2—C19—N5—C20	62.2 (7)
N4—C11—C15—C16	118.6 (6)	N2—C19—N5—C21	−169.8 (6)
N1—C11—C15—C16	−122.9 (6)	C22—C21—N5—C20	−177.9 (8)
C12—C11—C15—C16	2.2 (9)	C24—C21—N5—C20	−57.2 (10)
N2—C15—C16—O5'	166 (3)	C23—C21—N5—C20	60.8 (10)
N3—C15—C16—O5'	40 (3)	C22—C21—N5—C19	56.9 (9)
C11—C15—C16—O5'	−76 (3)	C24—C21—N5—C19	177.6 (8)
N2—C15—C16—O5	123.9 (17)	C23—C21—N5—C19	−64.4 (10)
N3—C15—C16—O5	−1.5 (19)	O5'—C16—O6—C17	−36 (3)
C11—C15—C16—O5	−117.3 (18)	O5—C16—O6—C17	7(2)
N2—C15—C16—O6'	−24.2 (17)	O6'—C16—O6—C17	91 (4)
N3—C15—C16—O6'	−149.6 (16)	C15—C16—O6—C17	−180.0 (17)
C11—C15—C16—O6'	94.6 (16)	C16—O6—C17—C18	−175 (4)
N2—C15—C16—O6	−49.9 (14)	O5'—C16—O6'—C17'	−6(3)
N3—C15—C16—O6	−175.3 (13)	O5—C16—O6'—C17'	37 (2)
C11—C15—C16—O6	68.9 (14)	O6—C16—O6'—C17'	−75 (3)
O1—C9—N1—C11	−169.0 (7)	C15—C16—O6'—C17'	−174.6 (14)
N2—C9—N1—C11	14.9 (8)	C16—O6'—C17'—C18'	124 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···Br2	0.97	2.59	3.190 (8)	120
C7—H7B···Br1	0.97	2.61	3.206 (7)	120
C7—H7A···O3i	0.97	2.55	3.125 (17)	118
C14—H14C···Cg1ii	0.97	2.97	3.89 (4)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯Br2	0.97	2.59	3.190 (8)	120
C7—H7B⋯Br1	0.97	2.61	3.206 (7)	120
C7—H7A⋯O3i	0.97	2.55	3.125 (17)	118
C14—H14C⋯Cg1ii	0.97	2.97	3.89 (4)	160

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the benzene C1–C6 ring.