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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o37–o38.
Published online 2007 December 6. doi:  10.1107/S1600536807062472
PMCID: PMC2914997

Diethyl 2-tert-butyl-6,9-dibromo-4,11-dioxo-5,10-dihydro-cis-1H,3H,4H,11H-2-azo-3a,4a,10a,11a-tetra­aza­benz[f]indeno[2,1,7-ija]azulene-11b,11c-dicarboxyl­ate

Abstract

In the title compound, C24H29Br2N5O6, a glycoluril derivative, the 1,4-dibromo­benzene 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 inter­molecular non-classical C—H(...)O hydrogen bond and a weak C—H(...)π inter­action. 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 [triangle]); Li et al. (2006 [triangle]). For potential applications of the title compound, see: Wu et al. (2002 [triangle]); Rowan et al. (1999 [triangle]); Chakraborty et al. (2002 [triangle]); Lehn (1995 [triangle]); Diederich (1991 [triangle]); Purse & Rebek (2005 [triangle]); Yin et al. (2006 [triangle]). For the crystal structures of similar compounds, see: Chen et al. (2007 [triangle]); Wang et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-00o37-scheme1.jpg

Experimental

Crystal data

  • C24H29Br2N5O6
  • M r = 643.34
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-00o37-efi1.jpg
  • 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 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

The authors thank Dr Xiang-Gao Meng for the X-ray data collection.

supplementary crystallographic information

Comment

Glycoluril derivatives have shown applications in many fields such as polymer cross-linking, explosives, slow-release fertilizers, iodogens stabilisers of organic compounds against photodegradation and reagent in combinatorial chemistry (Wu et al., 2002; Rowan et al., 1999; Chakraborty et al., 2002). Synthetic receptors with molecular cavities have been used as models and play an important role in studying the complex biological systems, such as protein folding, molecular recognition of substrates by enzymes, formation of membranes (Lehn, 1995; Diederich, 1991) and molecular catalysis (Purse & Rebek, 2005; Yin et al., 2006; Li et al., 2006). In addition, the crystal structures of glycoluril derivatives have been studied by our group (Chen et al., 2007; Wang et al., 2006). Herein we report the crystal structures of title compound (Fig. 1).

The dihedral angel between two five-membered rings in glycoluril unit is 69.8 (2)°. The six-membered ring of N2/C15/N3/C20/N5/C19 displays a chair conformation. By a combination of a non-classical H-bonding, e.g. C7—H7A···O3i [symmetry code: (i) 5/2 - x, 1/2 + y, 1/2 - z] and a weak C—H···π interaction (Table 1; Cg1 is the centroid of the benzene C1–C6 ring), molecules are joined together forming a one-dimensional chain running parallel to the b axis (Fig. 2).

Experimental

The title compound was synthesized according to the procedure of Lai & Yap (1993) and Li et al. (2006). Single crystals suitable for X-ray data collection were obtained by slow evaporation of a chloroform and methaol solution in a ratio of 20:1 at 293 K.

Refinement

Each diethoxycarbonyl group was treated as disordered over two positions. For the ester group containing O3/O4, the occupation factors of the two sites were refined by using restraint commands of DFIX, SADI and EDAP, giving the final occupancy of 0.73 (1)/0.27 (1) for the major and minor components, respectively. Similarly, the ester group containing O5/O6 was also treated as disorder and the final occupancy were 0.56 (1)/0.44 (1) for the corresponding components, respectively. The final largest residual density peak is located about 1.51 (1) Å from atom H5. Attempted to model the probable disorder or any other solvent molecules failed, which may be caused by the existence of the two heavy atoms, Br1 and Br2, leading to the contamination some positions. The large Rint value is probably due to the poor crystal quality; we tried to selected better crystals for diffraction experiment, but failed. All H atoms bonded to C atoms were located at the geometrical positions with C—H = 0.96 Å (methyl C), 0.97 Å (methylene C) and 0.93Å (aromatic C), and the Uiso(H) values were set k times of Ueq(C), k = 1.5 for methyl H atom and 1.2 for the other H atoms.

Figures

Fig. 1.
The molecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 10% probability level. H atoms are represented by spheres of arbitrary radius. Bonds to atoms of the minor disorder components are ...
Fig. 2.
Part of the crystal packing showing the formation of one-dimensional chain running parallel to the b axis by the C—H···O and C—H···π interactions. H atoms not involved in the motif ...

Crystal data

C24H29Br2N5O6F000 = 1304
Mr = 643.34Dx = 1.558 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2626 reflections
a = 10.4151 (8) Åθ = 2.2–18.8º
b = 11.3801 (8) ŵ = 3.00 mm1
c = 23.1649 (17) ÅT = 293 (2) K
β = 92.692 (1)ºBlock, blue
V = 2742.6 (3) Å30.10 × 0.06 × 0.04 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer2185 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.120
Monochromator: graphiteθmax = 25.0º
T = 293(2) Kθmin = 1.8º
[var phi] and ω scansh = −12→12
Absorption correction: nonek = −13→11
18064 measured reflectionsl = −27→25
4828 independent reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.080H-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 reflectionsΔρmax = 1.91 e Å3
415 parametersΔρmin = −0.53 e Å3
22 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
Br10.87255 (10)1.26953 (9)0.14865 (5)0.0940 (5)
Br21.27715 (11)0.96144 (11)0.00489 (5)0.1022 (5)
C11.0559 (7)1.0823 (7)0.1398 (3)0.0510 (19)
C21.1426 (7)1.0152 (7)0.1078 (4)0.056 (2)
C31.1591 (8)1.0401 (8)0.0494 (4)0.070 (3)
C41.0897 (10)1.1305 (9)0.0219 (4)0.077 (3)
H41.10111.1472−0.01680.093*
C51.0050 (9)1.1941 (8)0.0523 (5)0.078 (3)
H50.95771.25370.03380.093*
C60.9880 (7)1.1713 (7)0.1106 (4)0.062 (2)
C71.0491 (7)1.0630 (6)0.2031 (3)0.0517 (19)
H7A1.13461.07250.22090.062*
H7B0.99481.12340.21870.062*
C81.2156 (7)0.9152 (8)0.1365 (4)0.063 (2)
H8A1.26720.87700.10820.075*
H8B1.27380.94660.16660.075*
C90.8717 (7)0.9214 (6)0.2150 (3)0.0457 (18)
C101.0663 (7)0.7450 (6)0.1288 (4)0.051 (2)
C111.0791 (7)0.8450 (6)0.2169 (3)0.0475 (18)
C121.1894 (8)0.8394 (8)0.2628 (4)0.068 (2)
C131.2920 (14)0.9101 (19)0.3468 (8)0.074 (5)0.73 (3)
H13A1.36710.93910.32800.089*0.73 (3)
H13B1.30970.83090.36050.089*0.73 (3)
C141.261 (2)0.991 (2)0.3979 (8)0.107 (8)0.73 (3)
H14A1.23801.06740.38350.160*0.73 (3)
H14B1.33470.99650.42410.160*0.73 (3)
H14C1.19010.95820.41770.160*0.73 (3)
O31.2862 (18)0.7808 (19)0.2575 (12)0.124 (8)0.73 (3)
O41.1805 (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)
H13C1.27831.06140.34120.077*0.27 (3)
H13D1.36590.95490.32540.077*0.27 (3)
C14'1.260 (4)0.921 (4)0.3968 (16)0.061 (13)0.27 (3)
H14D1.22400.84380.39140.092*0.27 (3)
H14E1.20200.96890.41760.092*0.27 (3)
H14F1.34070.91520.41850.092*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)
C150.9798 (7)0.7420 (6)0.2205 (3)0.0448 (18)
C161.0060 (8)0.6547 (6)0.2707 (3)0.058 (2)
C190.7462 (7)0.7404 (7)0.2009 (3)0.054 (2)
H19A0.67200.79200.20100.065*
H19B0.72920.67270.22480.065*
C200.8754 (7)0.6202 (7)0.1429 (3)0.058 (2)
H20A0.88920.59070.10440.070*
H20B0.85730.55390.16760.070*
C210.6505 (8)0.6557 (8)0.1086 (4)0.070 (2)
C220.5477 (10)0.7499 (11)0.1080 (6)0.124 (5)
H22A0.53380.77440.14680.186*
H22B0.46910.71900.09070.186*
H22C0.57490.81600.08590.186*
C230.6001 (10)0.5414 (9)0.1369 (5)0.106 (4)
H23A0.66500.48160.13610.159*
H23B0.52410.51490.11570.159*
H23C0.58020.55720.17620.159*
C240.6860 (12)0.6247 (13)0.0476 (4)0.127 (5)
H24A0.74210.68400.03340.191*
H24B0.60940.62060.02290.191*
H24C0.72880.55000.04780.191*
N10.9991 (5)0.9471 (5)0.2194 (2)0.0448 (14)
N20.8576 (5)0.8014 (5)0.2239 (3)0.0495 (15)
N30.9906 (6)0.6825 (5)0.1656 (2)0.0486 (15)
N41.1327 (5)0.8276 (5)0.1619 (3)0.0484 (15)
N50.7677 (6)0.7018 (5)0.1411 (3)0.0511 (16)
O10.7850 (5)0.9907 (4)0.2079 (2)0.0591 (14)
O21.0786 (6)0.7265 (5)0.0781 (3)0.0711 (16)
O51.030 (3)0.5476 (9)0.2619 (7)0.064 (5)0.57 (4)
O60.986 (2)0.7074 (12)0.3223 (4)0.042 (4)0.57 (4)
C171.006 (4)0.641 (2)0.3743 (5)0.070 (8)0.57 (4)
H17A1.09550.61860.37930.084*0.57 (4)
H17B0.95470.56950.37170.084*0.57 (4)
C180.967 (5)0.714 (4)0.4262 (7)0.134 (19)0.57 (4)
H18A1.00180.79150.42350.201*0.57 (4)
H18B0.99950.67720.46120.201*0.57 (4)
H18C0.87480.71810.42640.201*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)
H17C1.02960.56540.35720.071*0.43 (4)
H17D0.88610.57830.37390.071*0.43 (4)
C18'1.006 (4)0.697 (3)0.4175 (12)0.058 (9)0.43 (4)
H18D1.08150.74070.40880.086*0.43 (4)
H18E1.02490.64680.45010.086*0.43 (4)
H18F0.93840.75050.42640.086*0.43 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0846 (8)0.0613 (6)0.1359 (11)0.0207 (5)0.0027 (6)0.0263 (6)
Br20.1050 (9)0.1171 (10)0.0874 (8)−0.0272 (7)0.0366 (6)−0.0131 (6)
C10.044 (4)0.050 (5)0.058 (5)−0.010 (4)−0.004 (4)0.004 (4)
C20.048 (4)0.055 (5)0.063 (6)−0.018 (4)−0.005 (4)0.007 (4)
C30.068 (6)0.078 (6)0.063 (6)−0.042 (5)−0.012 (5)0.015 (5)
C40.098 (8)0.079 (7)0.054 (6)−0.016 (6)−0.008 (5)0.017 (5)
C50.080 (7)0.055 (6)0.095 (8)−0.016 (5)−0.037 (6)0.029 (6)
C60.057 (5)0.056 (5)0.073 (6)−0.007 (4)−0.014 (4)0.016 (5)
C70.052 (5)0.038 (4)0.065 (5)−0.004 (3)−0.006 (4)−0.001 (4)
C80.046 (5)0.077 (6)0.066 (5)0.001 (4)0.010 (4)0.009 (5)
C90.052 (5)0.040 (5)0.044 (5)0.008 (4)−0.003 (4)0.003 (3)
C100.055 (5)0.041 (5)0.055 (6)0.014 (4)−0.002 (4)0.000 (4)
C110.051 (4)0.038 (4)0.053 (5)0.001 (3)−0.012 (4)0.004 (4)
C120.058 (6)0.067 (7)0.078 (8)0.006 (5)−0.026 (5)0.007 (6)
C130.066 (9)0.087 (13)0.066 (12)0.006 (9)−0.021 (8)0.019 (11)
C140.112 (14)0.102 (18)0.104 (17)−0.035 (15)−0.031 (11)−0.003 (13)
O30.094 (12)0.121 (13)0.15 (2)0.043 (11)−0.054 (11)−0.037 (11)
O40.056 (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)
C150.057 (5)0.033 (4)0.044 (4)0.005 (3)−0.005 (4)0.006 (3)
C160.071 (6)0.064 (6)0.037 (5)0.012 (5)−0.014 (4)0.015 (4)
C190.050 (5)0.053 (5)0.061 (5)0.000 (4)0.006 (4)0.004 (4)
C200.078 (6)0.051 (5)0.046 (5)−0.005 (4)0.001 (4)−0.003 (4)
C210.076 (6)0.071 (6)0.062 (6)−0.019 (5)−0.013 (5)0.008 (5)
C220.089 (8)0.112 (9)0.163 (12)0.003 (7)−0.075 (8)0.024 (8)
C230.097 (8)0.103 (8)0.115 (8)−0.063 (6)−0.026 (6)0.012 (7)
C240.130 (10)0.180 (13)0.069 (8)−0.028 (9)−0.025 (7)−0.005 (8)
N10.043 (4)0.041 (4)0.049 (4)0.007 (3)−0.005 (3)0.002 (3)
N20.041 (3)0.053 (4)0.054 (4)0.003 (3)−0.003 (3)0.002 (3)
N30.065 (4)0.043 (3)0.039 (3)0.000 (3)0.001 (3)0.004 (3)
N40.048 (4)0.048 (4)0.050 (4)0.004 (3)0.006 (3)−0.004 (3)
N50.056 (4)0.038 (4)0.058 (4)−0.002 (3)−0.009 (3)0.007 (3)
O10.054 (3)0.041 (3)0.082 (4)0.018 (3)−0.006 (3)0.004 (3)
O20.086 (4)0.081 (4)0.047 (4)0.016 (3)0.011 (3)0.002 (3)
O50.082 (13)0.040 (7)0.070 (8)0.018 (6)0.008 (8)0.017 (6)
O60.035 (9)0.050 (7)0.040 (7)−0.003 (6)−0.011 (5)0.009 (5)
C170.08 (2)0.071 (16)0.058 (16)0.005 (14)−0.015 (12)0.016 (14)
C180.14 (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)

Geometric parameters (Å, °)

Br1—C61.890 (9)C14'—H14E0.9600
Br2—C31.869 (10)C14'—H14F0.9600
C1—C61.392 (11)C15—N21.446 (9)
C1—C21.418 (11)C15—N31.451 (9)
C1—C71.488 (10)C15—C161.544 (9)
C2—C31.402 (11)C16—O5'1.260 (8)
C2—C81.505 (11)C16—O51.263 (8)
C3—C41.394 (13)C16—O6'1.350 (9)
C4—C51.362 (13)C16—O61.361 (8)
C4—H40.9300C19—N21.434 (9)
C5—C61.395 (13)C19—N51.480 (9)
C5—H50.9300C19—H19A0.9700
C7—N11.475 (9)C19—H19B0.9700
C7—H7A0.9700C20—N51.455 (9)
C7—H7B0.9700C20—N31.470 (9)
C8—N41.460 (9)C20—H20A0.9700
C8—H8A0.9700C20—H20B0.9700
C8—H8B0.9700C21—N51.498 (10)
C9—O11.204 (8)C21—C221.515 (14)
C9—N11.358 (9)C21—C241.520 (13)
C9—N21.391 (9)C21—C231.559 (12)
C10—O21.205 (9)C22—H22A0.9600
C10—N41.378 (9)C22—H22B0.9600
C10—N31.385 (10)C22—H22C0.9600
C11—N41.429 (9)C23—H23A0.9600
C11—N11.432 (8)C23—H23B0.9600
C11—C121.530 (11)C23—H23C0.9600
C11—C151.569 (10)C24—H24A0.9600
C12—O3'1.219 (14)C24—H24B0.9600
C12—O31.220 (12)C24—H24C0.9600
C12—O41.305 (9)O6—C171.429 (9)
C12—O4'1.352 (11)C17—C181.531 (10)
C13—O41.455 (10)C17—H17A0.9700
C13—C141.542 (10)C17—H17B0.9700
C13—H13A0.9700C18—H18A0.9600
C13—H13B0.9700C18—H18B0.9600
C14—H14A0.9600C18—H18C0.9600
C14—H14B0.9600O6'—C17'1.389 (10)
C14—H14C0.9600C17'—C18'1.540 (10)
C13'—O4'1.44 (5)C17'—H17C0.9700
C13'—C14'1.531 (11)C17'—H17D0.9700
C13'—H13C0.9700C18'—H18D0.9600
C13'—H13D0.9700C18'—H18E0.9600
C14'—H14D0.9600C18'—H18F0.9600
C6—C1—C2117.4 (7)O5'—C16—C15118.2 (13)
C6—C1—C7122.6 (7)O5—C16—C15121.9 (9)
C2—C1—C7119.7 (7)O6'—C16—C15108.2 (10)
C3—C2—C1120.3 (8)O6—C16—C15110.4 (8)
C3—C2—C8119.8 (8)N2—C19—N5109.6 (6)
C1—C2—C8119.9 (7)N2—C19—H19A109.7
C4—C3—C2120.4 (9)N5—C19—H19A109.7
C4—C3—Br2116.2 (7)N2—C19—H19B109.7
C2—C3—Br2123.3 (7)N5—C19—H19B109.7
C5—C4—C3119.4 (9)H19A—C19—H19B108.2
C5—C4—H4120.3N5—C20—N3108.5 (6)
C3—C4—H4120.3N5—C20—H20A110.0
C4—C5—C6121.0 (8)N3—C20—H20A110.0
C4—C5—H5119.5N5—C20—H20B110.0
C6—C5—H5119.5N3—C20—H20B110.0
C1—C6—C5121.4 (8)H20A—C20—H20B108.4
C1—C6—Br1121.6 (7)N5—C21—C22108.5 (8)
C5—C6—Br1117.0 (7)N5—C21—C24108.7 (7)
N1—C7—C1114.8 (6)C22—C21—C24110.9 (9)
N1—C7—H7A108.6N5—C21—C23111.4 (7)
C1—C7—H7A108.6C22—C21—C23110.1 (9)
N1—C7—H7B108.6C24—C21—C23107.3 (9)
C1—C7—H7B108.6C21—C22—H22A109.5
H7A—C7—H7B107.6C21—C22—H22B109.5
N4—C8—C2113.4 (6)H22A—C22—H22B109.5
N4—C8—H8A108.9C21—C22—H22C109.5
C2—C8—H8A108.9H22A—C22—H22C109.5
N4—C8—H8B108.9H22B—C22—H22C109.5
C2—C8—H8B108.9C21—C23—H23A109.5
H8A—C8—H8B107.7C21—C23—H23B109.5
O1—C9—N1126.4 (7)H23A—C23—H23B109.5
O1—C9—N2125.5 (7)C21—C23—H23C109.5
N1—C9—N2108.0 (6)H23A—C23—H23C109.5
O2—C10—N4126.0 (8)H23B—C23—H23C109.5
O2—C10—N3126.8 (7)C21—C24—H24A109.5
N4—C10—N3107.1 (7)C21—C24—H24B109.5
N4—C11—N1113.7 (6)H24A—C24—H24B109.5
N4—C11—C12107.6 (6)C21—C24—H24C109.5
N1—C11—C12115.1 (6)H24A—C24—H24C109.5
N4—C11—C15103.3 (6)H24B—C24—H24C109.5
N1—C11—C15102.6 (5)C9—N1—C11113.0 (6)
C12—C11—C15114.0 (6)C9—N1—C7121.9 (6)
O3—C12—O4120.5 (14)C11—N1—C7120.1 (6)
O3'—C12—O4'130 (3)C9—N2—C19120.6 (6)
O3'—C12—C11119 (3)C9—N2—C15110.6 (6)
O3—C12—C11123.4 (13)C19—N2—C15116.9 (6)
O4—C12—C11115.8 (9)C10—N3—C15111.7 (6)
O4'—C12—C11107.9 (19)C10—N3—C20120.4 (6)
O4—C13—C14107.3 (9)C15—N3—C20116.3 (6)
O4—C13—H13A110.3C10—N4—C11112.6 (6)
C14—C13—H13A110.3C10—N4—C8122.2 (7)
O4—C13—H13B110.3C11—N4—C8121.8 (6)
C14—C13—H13B110.3C20—N5—C19108.3 (6)
H13A—C13—H13B108.5C20—N5—C21113.5 (6)
C12—O4—C13114.3 (12)C19—N5—C21114.7 (6)
O4'—C13'—C14'111 (3)C16—O6—C17119.0 (10)
O4'—C13'—H13C109.5O6—C17—C18110.0 (10)
C14'—C13'—H13C109.5O6—C17—H17A109.7
O4'—C13'—H13D109.5C18—C17—H17A109.7
C14'—C13'—H13D109.5O6—C17—H17B109.7
H13C—C13'—H13D108.0C18—C17—H17B109.7
C13'—C14'—H14D109.5H17A—C17—H17B108.2
C13'—C14'—H14E109.5C16—O6'—C17'112.5 (19)
H14D—C14'—H14E109.5O6'—C17'—C18'112.5 (11)
C13'—C14'—H14F109.5O6'—C17'—H17C109.1
H14D—C14'—H14F109.5C18'—C17'—H17C109.1
H14E—C14'—H14F109.5O6'—C17'—H17D109.1
C12—O4'—C13'126 (4)C18'—C17'—H17D109.1
N2—C15—N3111.7 (6)H17C—C17'—H17D107.8
N2—C15—C16112.6 (6)C17'—C18'—H18D109.5
N3—C15—C16110.0 (5)C17'—C18'—H18E109.5
N2—C15—C11103.7 (5)H18D—C18'—H18E109.5
N3—C15—C11102.9 (5)C17'—C18'—H18F109.5
C16—C15—C11115.4 (6)H18D—C18'—H18F109.5
O5'—C16—O6'132.6 (12)H18E—C18'—H18F109.5
O5—C16—O6127.4 (9)
C6—C1—C2—C30.8 (10)O1—C9—N1—C7−14.0 (11)
C7—C1—C2—C3−173.8 (6)N2—C9—N1—C7169.9 (6)
C6—C1—C2—C8−178.1 (7)N4—C11—N1—C9101.4 (7)
C7—C1—C2—C87.4 (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—C4178.4 (7)N4—C11—N1—C7−54.1 (8)
C1—C2—C3—Br2176.8 (5)C12—C11—N1—C770.7 (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—C1176.3 (8)
C3—C4—C5—C60.9 (13)O1—C9—N2—C1928.2 (11)
C2—C1—C6—C5−0.3 (11)N1—C9—N2—C19−155.8 (6)
C7—C1—C6—C5174.1 (7)O1—C9—N2—C15169.9 (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—C987.2 (8)
C4—C5—C6—C1−0.6 (13)N5—C19—N2—C15−52.3 (8)
C4—C5—C6—Br1177.7 (7)N3—C15—N2—C9−102.2 (7)
C6—C1—C7—N1119.2 (7)C16—C15—N2—C9133.3 (6)
C2—C1—C7—N1−66.5 (9)C11—C15—N2—C97.9 (7)
C3—C2—C8—N4−122.8 (7)N3—C15—N2—C1941.0 (8)
C1—C2—C8—N456.1 (10)C16—C15—N2—C19−83.5 (8)
N4—C11—C12—O3'−71 (2)C11—C15—N2—C19151.1 (6)
N1—C11—C12—O3'161 (2)O2—C10—N3—C15−169.2 (7)
C15—C11—C12—O3'43 (3)N4—C10—N3—C1515.2 (8)
N4—C11—C12—O3−30 (2)O2—C10—N3—C20−27.3 (11)
N1—C11—C12—O3−157.6 (19)N4—C10—N3—C20157.1 (6)
C15—C11—C12—O384 (2)N2—C15—N3—C10102.2 (7)
N4—C11—C12—O4143.8 (16)C16—C15—N3—C10−131.8 (6)
N1—C11—C12—O415.8 (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—C2084.5 (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—C1339 (3)N5—C20—N3—C1553.6 (8)
O3—C12—O4—C13−1(3)O2—C10—N4—C11168.1 (7)
O4'—C12—O4—C13−109 (11)N3—C10—N4—C11−16.2 (8)
C11—C12—O4—C13−175.0 (15)O2—C10—N4—C88.7 (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—C10131.5 (6)
O4—C12—O4'—C13'70 (7)C15—C11—N4—C1010.6 (7)
C11—C12—O4'—C13'−170 (4)N1—C11—N4—C859.7 (8)
C14'—C13'—O4'—C12−87 (8)C12—C11—N4—C8−69.0 (8)
N4—C11—C15—N2−117.7 (6)C15—C11—N4—C8170.1 (6)
N1—C11—C15—N20.7 (7)C2—C8—N4—C1077.2 (9)
C12—C11—C15—N2125.8 (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—N3117.2 (6)N3—C20—N5—C21169.2 (6)
C12—C11—C15—N3−117.6 (7)N2—C19—N5—C2062.2 (7)
N4—C11—C15—C16118.6 (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—C162.2 (9)C24—C21—N5—C20−57.2 (10)
N2—C15—C16—O5'166 (3)C23—C21—N5—C2060.8 (10)
N3—C15—C16—O5'40 (3)C22—C21—N5—C1956.9 (9)
C11—C15—C16—O5'−76 (3)C24—C21—N5—C19177.6 (8)
N2—C15—C16—O5123.9 (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—C177(2)
N2—C15—C16—O6'−24.2 (17)O6'—C16—O6—C1791 (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—O668.9 (14)O6—C16—O6'—C17'−75 (3)
O1—C9—N1—C11−169.0 (7)C15—C16—O6'—C17'−174.6 (14)
N2—C9—N1—C1114.9 (8)C16—O6'—C17'—C18'124 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C8—H8A···Br20.972.593.190 (8)120
C7—H7B···Br10.972.613.206 (7)120
C7—H7A···O3i0.972.553.125 (17)118
C14—H14C···Cg1ii0.972.973.89 (4)160

Symmetry codes: (i) −x+5/2, y+1/2, −z+1/2; (ii) −x+5/2, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2227).

References

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