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Acta Cryst. (2009). E65, o674    [ doi:10.1107/S1600536809005157 ]

Diethyl 2,6-(2,4-dichlorophenyl)-4,8-dioxo-2,3,6,7-tetrahydro-1H,5H-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluorene-8b,8c-dicarboxylate

J. Ding, X. Ren, Y. Zhu, N. She and A.-X. Wu

Abstract top

The title molecule, C28H28Cl4N6O6, is built up from four fused rings, viz. two nearly planar imidazole five-membered rings which adopt envelope conformations with the C=O groups at the flap position, and two triazine six-membered rings which adopt chair conformations. Each six-membered ring has a 2,4-dichlorobenzyl substituent attached to an N atom. In the molecule, the two ethyl groups are each disordered between two orientations in 0.784 (16)/0.216 (16) and 0.631 (10)/0.37 (10) ratios. Weak intermolecular C-H...O hydrogen bonds help to stabilize the crystal packing.

Comment top

Glycoluril derivatives have been used in a variety of applications including polymer cross-linking, explosives, in the stabilization of organic compounds against photodegradation, textile waste stream purification, combinatorial chemistry, in the fields of cucurbituril chemistry and anion sensors (Freeman et al., 1981; Rebek, 2005; Rowan et al., 1999; Wu et al., 2002). As a part of our ongoing investigation into glycoluril derivatives (Li et al., 2006; Cao et al., 2008), we report here the structure of the title compound (I) (Fig. 1).

The molecular structure of (I) is shown in Fig. 1. The crystal packing exhibits weak intermolecular non-classical C—H···O hydrogen bonds (Table 1).

Related literature top

For the preparation of the title compound, see: Li et al. (2006). For general background to glycoluril and its derivatives, see: Freeman et al. (1981); Rebek (2005); Rowan et al. (1999); Wu et al. (2002); Cao et al. (2008).

Experimental top

The title compound was synthesized according to the known procedure (Li et al. (2006) in 10% isolated yield. Crystals of (I) suitable for X-ray data collection were obtained by slow evaporation of a chloroform and methaol solution in ratio of 20:1 at 298 K.

Refinement top

C-bound H atoms were initially located on a difference Fourier map, but placed in idealized positions [C–H 0.93-0.97 Å] and refined as riding, with their Uiso values being set 1.2 (or 1.5 for methyl) times of Ueq(C). Two ethyl groups were treated as disordered between two positions each with the refined occupancies 0.784 (16)/0.216 (16) for C14-C15/C14'-C15' and 0.63 (2)/0.37 (2) for C18-C19/C18'-C19'.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. Only major parts of disordered atoms are shown. H atoms are represented by spheres of arbitrary radius.
Diethyl 2,6-(2,4-dichlorophenyl)-4,8-dioxo-2,3,6,7-tetrahydro-1H,5H- 2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluorene-8b,8c-dicarboxylate top
Crystal data top
C28H28Cl4N6O6F(000) = 1416
Mr = 686.36Dx = 1.495 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7626 reflections
a = 10.0030 (11) Åθ = 2.3–24.5°
b = 27.1742 (15) ŵ = 0.44 mm−1
c = 11.2427 (2) ÅT = 292 K
β = 93.716 (4)°Block, colorless
V = 3049.6 (4) Å30.20 × 0.20 × 0.10 mm
Z = 4
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer		5308 independent reflections
Radiation source: fine-focus sealed tube3773 reflections with I > 2σ(I)
graphiteRint = 0.060
φ and ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick,1996)		h = −11→11
Tmin = 0.907, Tmax = 0.957k = −32→32
24973 measured reflectionsl = −13→13
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0927P)2 + 1.4271P]
where P = (Fo2 + 2Fc2)/3
5308 reflections(Δ/σ)max < 0.001
439 parametersΔρmax = 0.47 e Å−3
0 restraintsΔρmin = −0.38 e Å−3
Crystal data top
C28H28Cl4N6O6V = 3049.6 (4) Å3
Mr = 686.36Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.0030 (11) ŵ = 0.44 mm−1
b = 27.1742 (15) ÅT = 292 K
c = 11.2427 (2) Å0.20 × 0.20 × 0.10 mm
β = 93.716 (4)°
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer		5308 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick,1996)		3773 reflections with I > 2σ(I)
Tmin = 0.907, Tmax = 0.957Rint = 0.060
24973 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.063H-atom parameters constrained
wR(F2) = 0.179Δρmax = 0.47 e Å−3
S = 1.06Δρmin = −0.38 e Å−3
5308 reflectionsAbsolute structure: ?
439 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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 F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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) top
xyzUiso*/UeqOcc. (<1)
C10.5525 (4)0.12607 (15)0.4170 (3)0.0593 (9)
C20.4750 (4)0.08583 (14)0.4444 (3)0.0608 (10)
C30.4554 (5)0.04567 (16)0.3692 (4)0.0761 (12)
H30.40330.01900.38930.091*
C40.5181 (6)0.0474 (2)0.2614 (4)0.0884 (15)
C50.5934 (6)0.0862 (2)0.2305 (4)0.0938 (16)
H50.63240.08670.15770.113*
C60.6112 (5)0.12488 (19)0.3089 (4)0.0811 (13)
H60.66460.15120.28850.097*
C70.5659 (4)0.17040 (14)0.4962 (3)0.0621 (10)
H7A0.58340.16010.57830.074*
H7B0.64080.19030.47390.074*
C80.4272 (4)0.22419 (13)0.3692 (3)0.0552 (9)
H8A0.49600.24910.36360.066*
H8B0.43630.20050.30550.066*
C90.4369 (4)0.23568 (15)0.5801 (3)0.0591 (9)
H9A0.45050.21970.65700.071*
H9B0.50700.26000.57350.071*
C100.2018 (4)0.24165 (12)0.6322 (3)0.0495 (8)
C110.1878 (4)0.21790 (12)0.3179 (3)0.0495 (8)
C120.2615 (4)0.27858 (12)0.4541 (3)0.0509 (8)
C130.3251 (5)0.33054 (15)0.4367 (4)0.0720 (11)
C140.3744 (8)0.4047 (2)0.5355 (7)0.108 (3)0.784 (16)
H14A0.46300.39880.50820.129*0.784 (16)
H14B0.38380.41580.61770.129*0.784 (16)
C150.3013 (12)0.4432 (3)0.4579 (9)0.121 (4)0.784 (16)
H15A0.30010.43320.37590.182*0.784 (16)
H15B0.34660.47420.46760.182*0.784 (16)
H15C0.21100.44640.48110.182*0.784 (16)
C14'0.274 (2)0.4048 (4)0.4613 (15)0.18 (2)0.216 (16)
H14C0.18580.41800.47390.212*0.216 (16)
H14D0.27930.39890.37660.212*0.216 (16)
C15'0.382 (4)0.4420 (7)0.505 (3)0.110 (12)0.216 (16)
H15D0.46870.43020.48550.165*0.216 (16)
H15E0.38090.44600.58960.165*0.216 (16)
H15F0.36500.47320.46650.165*0.216 (16)
C160.1056 (4)0.27423 (12)0.4550 (3)0.0484 (8)
C170.0320 (4)0.32152 (14)0.4156 (3)0.0631 (10)
C18−0.1608 (16)0.3697 (5)0.4237 (8)0.092 (4)0.63 (2)
H18A−0.22730.35560.36690.110*0.63 (2)
H18B−0.11030.39430.38320.110*0.63 (2)
C19−0.2273 (14)0.3923 (5)0.5272 (9)0.100 (4)0.63 (2)
H19A−0.27690.36740.56620.150*0.63 (2)
H19B−0.28710.41790.49860.150*0.63 (2)
H19C−0.16020.40580.58270.150*0.63 (2)
C18'−0.1345 (16)0.3784 (5)0.470 (3)0.125 (10)0.37 (2)
H18C−0.11570.39570.39750.149*0.37 (2)
H18D−0.10470.39850.53810.149*0.37 (2)
C19'−0.2851 (13)0.3666 (8)0.472 (2)0.099 (7)0.37 (2)
H19D−0.30910.34230.41260.149*0.37 (2)
H19E−0.33630.39600.45590.149*0.37 (2)
H19F−0.30370.35410.54920.149*0.37 (2)
C20−0.0401 (4)0.22538 (12)0.5846 (3)0.0521 (8)
H20A−0.03750.21130.66400.063*
H20B−0.11890.24610.57500.063*
C21−0.0462 (4)0.20626 (13)0.3782 (3)0.0535 (9)
H21A−0.12550.22620.36040.064*
H21B−0.04760.17950.32100.064*
C220.0446 (4)0.14521 (12)0.5236 (3)0.0517 (8)
H22A0.05020.13870.60860.062*
H22B0.13270.15520.50160.062*
C230.0040 (4)0.09876 (12)0.4576 (3)0.0497 (8)
C24−0.1053 (4)0.07018 (12)0.4858 (3)0.0509 (8)
C25−0.1439 (4)0.02843 (13)0.4219 (3)0.0575 (9)
H25−0.21830.01040.44140.069*
C26−0.0694 (4)0.01411 (13)0.3284 (3)0.0606 (10)
C270.0420 (4)0.03969 (14)0.3000 (3)0.0647 (10)
H270.09280.02900.23860.078*
C280.0779 (4)0.08189 (13)0.3645 (3)0.0610 (10)
H280.15340.09940.34510.073*
Cl10.39824 (13)0.08382 (4)0.57796 (9)0.0830 (4)
Cl20.4914 (2)−0.00226 (7)0.16389 (14)0.1478 (8)
Cl3−0.12054 (14)−0.03781 (4)0.24604 (10)0.0876 (4)
Cl4−0.19505 (11)0.08564 (4)0.60790 (8)0.0677 (3)
N10.4431 (3)0.19939 (10)0.4851 (2)0.0510 (7)
N20.3063 (3)0.25959 (11)0.5705 (2)0.0512 (7)
N30.2952 (3)0.24689 (10)0.3574 (2)0.0501 (7)
N40.0814 (3)0.25627 (9)0.5739 (2)0.0459 (7)
N50.0733 (3)0.23663 (10)0.3637 (2)0.0490 (7)
N6−0.0517 (3)0.18581 (10)0.4971 (2)0.0493 (7)
O10.2128 (3)0.21891 (10)0.72513 (19)0.0629 (7)
O20.1917 (3)0.18332 (10)0.2502 (2)0.0650 (7)
O30.3988 (4)0.34020 (11)0.3645 (4)0.1084 (13)
O40.2940 (4)0.35954 (12)0.5261 (3)0.0995 (11)
O50.0633 (4)0.34460 (12)0.3319 (3)0.1093 (13)
O6−0.0697 (4)0.33056 (11)0.4754 (3)0.0944 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.046 (2)0.072 (2)0.060 (2)0.0109 (19)0.0016 (17)0.0043 (17)
C20.053 (2)0.072 (2)0.0572 (19)0.013 (2)0.0034 (17)0.0001 (17)
C30.083 (3)0.071 (3)0.073 (2)0.008 (2)−0.003 (2)−0.006 (2)
C40.102 (4)0.096 (4)0.066 (3)0.031 (3)−0.007 (3)−0.018 (2)
C50.091 (4)0.123 (5)0.069 (3)0.027 (3)0.026 (3)0.001 (3)
C60.068 (3)0.100 (3)0.077 (3)0.014 (3)0.018 (2)0.008 (2)
C70.043 (2)0.073 (2)0.069 (2)0.0011 (18)−0.0029 (17)0.0057 (18)
C80.058 (2)0.058 (2)0.0500 (17)−0.0012 (18)0.0086 (16)0.0056 (15)
C90.049 (2)0.077 (2)0.0511 (18)−0.0035 (19)−0.0026 (16)−0.0068 (17)
C100.058 (2)0.0524 (19)0.0378 (15)−0.0023 (16)−0.0012 (15)−0.0088 (13)
C110.063 (2)0.0509 (18)0.0347 (14)0.0051 (17)0.0006 (15)0.0049 (13)
C120.060 (2)0.0444 (17)0.0491 (16)−0.0005 (16)0.0061 (15)0.0001 (13)
C130.080 (3)0.057 (2)0.081 (3)−0.004 (2)0.027 (2)−0.008 (2)
C140.106 (6)0.079 (5)0.140 (7)−0.018 (5)0.019 (5)−0.031 (5)
C150.151 (12)0.105 (7)0.110 (7)−0.014 (7)0.030 (7)0.011 (5)
C14'0.18 (5)0.18 (5)0.17 (4)0.01 (4)0.01 (3)0.00 (4)
C15'0.11 (3)0.10 (3)0.12 (3)0.00 (2)0.018 (19)−0.01 (2)
C160.060 (2)0.0430 (17)0.0423 (15)0.0033 (16)0.0027 (15)0.0004 (13)
C170.072 (3)0.051 (2)0.066 (2)0.0129 (19)0.000 (2)−0.0007 (18)
C180.113 (11)0.081 (6)0.081 (7)0.060 (6)0.003 (5)0.018 (5)
C190.100 (9)0.103 (8)0.097 (6)0.039 (7)0.011 (6)0.002 (5)
C18'0.113 (19)0.130 (18)0.13 (2)0.020 (14)0.001 (16)−0.001 (15)
C19'0.097 (13)0.106 (14)0.095 (12)0.011 (10)0.004 (10)0.026 (10)
C200.051 (2)0.0533 (19)0.0520 (17)0.0072 (16)0.0061 (15)−0.0025 (14)
C210.050 (2)0.0559 (19)0.0527 (18)0.0066 (17)−0.0107 (16)−0.0028 (15)
C220.050 (2)0.0482 (18)0.0563 (18)0.0040 (15)−0.0042 (16)0.0011 (14)
C230.048 (2)0.0466 (18)0.0533 (17)0.0039 (16)−0.0074 (15)0.0047 (14)
C240.046 (2)0.0503 (18)0.0555 (18)0.0068 (16)−0.0051 (15)0.0072 (14)
C250.054 (2)0.052 (2)0.065 (2)−0.0055 (17)−0.0065 (18)0.0079 (16)
C260.070 (3)0.0468 (19)0.063 (2)0.0026 (18)−0.0148 (19)−0.0009 (16)
C270.078 (3)0.054 (2)0.063 (2)0.004 (2)0.0075 (19)−0.0032 (17)
C280.065 (3)0.054 (2)0.064 (2)−0.0024 (18)0.0025 (18)0.0014 (16)
Cl10.1020 (10)0.0801 (7)0.0695 (6)−0.0051 (6)0.0263 (6)0.0059 (5)
Cl20.207 (2)0.1358 (14)0.0978 (10)0.0362 (13)−0.0166 (11)−0.0540 (10)
Cl30.1073 (10)0.0689 (7)0.0841 (7)−0.0126 (6)−0.0125 (6)−0.0194 (5)
Cl40.0647 (7)0.0725 (6)0.0667 (6)0.0066 (5)0.0095 (5)0.0043 (4)
N10.0473 (18)0.0591 (17)0.0463 (14)0.0018 (14)0.0008 (12)0.0033 (12)
N20.0467 (19)0.0648 (18)0.0421 (13)−0.0064 (14)0.0030 (12)−0.0047 (12)
N30.059 (2)0.0498 (15)0.0419 (13)0.0031 (13)0.0039 (12)0.0020 (11)
N40.0463 (18)0.0474 (14)0.0440 (13)0.0013 (12)0.0036 (12)−0.0033 (11)
N50.055 (2)0.0490 (15)0.0422 (13)0.0025 (13)−0.0017 (13)−0.0004 (11)
N60.0467 (18)0.0474 (15)0.0533 (14)0.0034 (13)−0.0012 (13)−0.0005 (12)
O10.0677 (18)0.0818 (17)0.0387 (11)−0.0032 (14)−0.0007 (11)0.0032 (11)
O20.079 (2)0.0672 (16)0.0484 (12)0.0052 (14)0.0034 (12)−0.0155 (12)
O30.140 (4)0.0620 (19)0.132 (3)−0.016 (2)0.075 (3)0.0008 (18)
O40.114 (3)0.0619 (18)0.128 (3)−0.0258 (19)0.047 (2)−0.0256 (19)
O50.140 (3)0.082 (2)0.109 (2)0.032 (2)0.025 (2)0.045 (2)
O60.110 (3)0.074 (2)0.101 (2)0.047 (2)0.026 (2)0.0228 (17)
Geometric parameters (Å, °) top
C1—C61.384 (6)C15'—H15D0.9600
C1—C21.387 (5)C15'—H15E0.9600
C1—C71.499 (5)C15'—H15F0.9600
C2—C31.387 (5)C16—N41.457 (4)
C2—Cl11.731 (4)C16—N51.469 (4)
C3—C41.401 (7)C16—C171.532 (5)
C3—H30.9300C17—O51.189 (5)
C4—C51.354 (7)C17—O61.279 (5)
C4—Cl21.749 (5)C18—O61.494 (7)
C5—C61.375 (7)C18—C191.508 (9)
C5—H50.9300C18—H18A0.9700
C6—H60.9300C18—H18B0.9700
C7—N11.458 (4)C19—H19A0.9600
C7—H7A0.9700C19—H19B0.9600
C7—H7B0.9700C19—H19C0.9600
C8—N31.456 (5)C18'—O61.453 (10)
C8—N11.467 (4)C18'—C19'1.542 (11)
C8—H8A0.9700C18'—H18C0.9700
C8—H8B0.9700C18'—H18D0.9700
C9—N21.456 (5)C19'—H19D0.9600
C9—N11.458 (4)C19'—H19E0.9600
C9—H9A0.9700C19'—H19F0.9600
C9—H9B0.9700C20—N61.457 (4)
C10—O11.213 (4)C20—N41.488 (4)
C10—N21.381 (5)C20—H20A0.9700
C10—N41.392 (4)C20—H20B0.9700
C11—O21.212 (4)C21—N61.452 (4)
C11—N31.382 (4)C21—N51.471 (5)
C11—N51.383 (4)C21—H21A0.9700
C12—N31.443 (4)C21—H21B0.9700
C12—N21.450 (4)C22—N61.482 (4)
C12—C161.566 (5)C22—C231.507 (4)
C12—C131.566 (5)C22—H22A0.9700
C13—O31.161 (5)C22—H22B0.9700
C13—O41.330 (5)C23—C241.395 (5)
C14—O41.467 (6)C23—C281.397 (5)
C14—C151.518 (8)C24—C251.384 (5)
C14—H14A0.9700C24—Cl41.740 (4)
C14—H14B0.9700C25—C261.382 (6)
C15—H15A0.9600C25—H250.9300
C15—H15B0.9600C26—C271.369 (6)
C15—H15C0.9600C26—Cl31.746 (4)
C14'—O41.438 (11)C27—C281.392 (5)
C14'—C15'1.539 (11)C27—H270.9300
C14'—H14C0.9700C28—H280.9300
C14'—H14D0.9700
C6—C1—C2116.9 (4)O6—C17—C16113.1 (3)
C6—C1—C7120.9 (4)O6—C18—C19106.1 (6)
C2—C1—C7122.1 (3)O6—C18—H18A110.5
C3—C2—C1122.9 (4)C19—C18—H18A110.5
C3—C2—Cl1116.8 (3)O6—C18—H18B110.5
C1—C2—Cl1120.2 (3)C19—C18—H18B110.5
C2—C3—C4116.6 (5)H18A—C18—H18B108.7
C2—C3—H3121.7O6—C18'—C19'104.3 (9)
C4—C3—H3121.7O6—C18'—H18C110.9
C5—C4—C3122.4 (4)C19'—C18'—H18C110.9
C5—C4—Cl2120.4 (4)O6—C18'—H18D110.9
C3—C4—Cl2117.2 (5)C19'—C18'—H18D110.9
C4—C5—C6118.8 (5)H18C—C18'—H18D108.9
C4—C5—H5120.6C18'—C19'—H19D109.5
C6—C5—H5120.6C18'—C19'—H19E109.5
C5—C6—C1122.4 (5)H19D—C19'—H19E109.5
C5—C6—H6118.8C18'—C19'—H19F109.5
C1—C6—H6118.8H19D—C19'—H19F109.5
N1—C7—C1109.9 (3)H19E—C19'—H19F109.5
N1—C7—H7A109.7N6—C20—N4113.0 (3)
C1—C7—H7A109.7N6—C20—H20A109.0
N1—C7—H7B109.7N4—C20—H20A109.0
C1—C7—H7B109.7N6—C20—H20B109.0
H7A—C7—H7B108.2N4—C20—H20B109.0
N3—C8—N1108.7 (3)H20A—C20—H20B107.8
N3—C8—H8A109.9N6—C21—N5113.3 (2)
N1—C8—H8A109.9N6—C21—H21A108.9
N3—C8—H8B109.9N5—C21—H21A108.9
N1—C8—H8B109.9N6—C21—H21B108.9
H8A—C8—H8B108.3N5—C21—H21B108.9
N2—C9—N1109.2 (3)H21A—C21—H21B107.7
N2—C9—H9A109.8N6—C22—C23111.9 (2)
N1—C9—H9A109.8N6—C22—H22A109.2
N2—C9—H9B109.8C23—C22—H22A109.2
N1—C9—H9B109.8N6—C22—H22B109.2
H9A—C9—H9B108.3C23—C22—H22B109.2
O1—C10—N2125.7 (3)H22A—C22—H22B107.9
O1—C10—N4125.4 (3)C24—C23—C28116.7 (3)
N2—C10—N4108.9 (3)C24—C23—C22123.0 (3)
O2—C11—N3126.0 (4)C28—C23—C22120.3 (3)
O2—C11—N5125.5 (3)C25—C24—C23122.3 (4)
N3—C11—N5108.4 (3)C25—C24—Cl4117.8 (3)
N3—C12—N2113.2 (3)C23—C24—Cl4119.8 (3)
N3—C12—C16104.0 (3)C26—C25—C24118.7 (4)
N2—C12—C16102.5 (3)C26—C25—H25120.7
N3—C12—C13109.1 (3)C24—C25—H25120.7
N2—C12—C13109.2 (3)C27—C26—C25121.4 (3)
C16—C12—C13118.8 (3)C27—C26—Cl3120.1 (3)
O3—C13—O4125.7 (4)C25—C26—Cl3118.5 (3)
O3—C13—C12124.9 (4)C26—C27—C28118.9 (4)
O4—C13—C12108.9 (4)C26—C27—H27120.5
O4—C14—C15107.0 (6)C28—C27—H27120.5
O4—C14—H14A110.3C27—C28—C23121.9 (4)
C15—C14—H14A110.3C27—C28—H28119.0
O4—C14—H14B110.3C23—C28—H28119.0
C15—C14—H14B110.3C7—N1—C9112.3 (3)
H14A—C14—H14B108.6C7—N1—C8111.5 (3)
O4—C14'—C15'109.2 (11)C9—N1—C8109.4 (3)
O4—C14'—H14C109.8C10—N2—C12112.3 (3)
C15'—C14'—H14C109.8C10—N2—C9120.7 (3)
O4—C14'—H14D109.8C12—N2—C9116.6 (3)
C15'—C14'—H14D109.8C11—N3—C12111.6 (3)
H14C—C14'—H14D108.3C11—N3—C8118.0 (3)
C14'—C15'—H15D109.5C12—N3—C8116.0 (3)
C14'—C15'—H15E109.5C10—N4—C16109.7 (3)
H15D—C15'—H15E109.5C10—N4—C20119.1 (3)
C14'—C15'—H15F109.5C16—N4—C20116.6 (2)
H15D—C15'—H15F109.5C11—N5—C16111.5 (3)
H15E—C15'—H15F109.5C11—N5—C21122.3 (3)
N4—C16—N5111.5 (3)C16—N5—C21117.2 (3)
N4—C16—C17116.2 (3)C21—N6—C20109.5 (3)
N5—C16—C17107.5 (2)C21—N6—C22114.0 (3)
N4—C16—C12104.8 (2)C20—N6—C22113.0 (2)
N5—C16—C12102.8 (3)C13—O4—C14'99.0 (6)
C17—C16—C12113.2 (3)C13—O4—C14113.4 (4)
O5—C17—O6125.0 (4)C17—O6—C18'121.3 (13)
O5—C17—C16121.7 (4)C17—O6—C18114.7 (6)
C6—C1—C2—C30.1 (6)N3—C12—N2—C939.0 (4)
C7—C1—C2—C3176.3 (3)C16—C12—N2—C9150.3 (3)
C6—C1—C2—Cl1179.7 (3)C13—C12—N2—C9−82.8 (4)
C7—C1—C2—Cl1−4.1 (5)N1—C9—N2—C1092.2 (3)
C1—C2—C3—C4−0.2 (6)N1—C9—N2—C12−50.0 (4)
Cl1—C2—C3—C4−179.8 (3)O2—C11—N3—C12−168.9 (3)
C2—C3—C4—C5−0.5 (7)N5—C11—N3—C1214.2 (3)
C2—C3—C4—Cl2−178.6 (3)O2—C11—N3—C8−30.8 (4)
C3—C4—C5—C61.3 (8)N5—C11—N3—C8152.4 (3)
Cl2—C4—C5—C6179.3 (4)N2—C12—N3—C1198.8 (3)
C4—C5—C6—C1−1.5 (7)C16—C12—N3—C11−11.7 (3)
C2—C1—C6—C50.8 (6)C13—C12—N3—C11−139.3 (3)
C7—C1—C6—C5−175.5 (4)N2—C12—N3—C8−40.2 (4)
C6—C1—C7—N1101.8 (4)C16—C12—N3—C8−150.7 (3)
C2—C1—C7—N1−74.3 (4)C13—C12—N3—C881.6 (4)
N3—C12—C13—O3−7.4 (6)N1—C8—N3—C11−83.9 (3)
N2—C12—C13—O3116.8 (5)N1—C8—N3—C1252.4 (4)
C16—C12—C13—O3−126.2 (5)O1—C10—N4—C16−169.2 (3)
N3—C12—C13—O4−179.9 (4)N2—C10—N4—C1614.1 (3)
N2—C12—C13—O4−55.6 (5)O1—C10—N4—C20−31.0 (4)
C16—C12—C13—O461.3 (5)N2—C10—N4—C20152.3 (3)
N3—C12—C16—N4121.5 (3)N5—C16—N4—C1099.9 (3)
N2—C12—C16—N43.4 (3)C17—C16—N4—C10−136.4 (3)
C13—C12—C16—N4−117.1 (3)C12—C16—N4—C10−10.6 (3)
N3—C12—C16—N54.8 (3)N5—C16—N4—C20−39.4 (4)
N2—C12—C16—N5−113.3 (3)C17—C16—N4—C2084.3 (4)
C13—C12—C16—N5126.3 (3)C12—C16—N4—C20−149.9 (3)
N3—C12—C16—C17−110.9 (3)N6—C20—N4—C10−86.1 (3)
N2—C12—C16—C17131.0 (3)N6—C20—N4—C1649.3 (4)
C13—C12—C16—C1710.5 (4)O2—C11—N5—C16172.4 (3)
N4—C16—C17—O5165.1 (4)N3—C11—N5—C16−10.7 (3)
N5—C16—C17—O5−69.3 (5)O2—C11—N5—C2126.5 (4)
C12—C16—C17—O543.6 (5)N3—C11—N5—C21−156.6 (2)
N4—C16—C17—O6−20.0 (5)N4—C16—N5—C11−108.5 (3)
N5—C16—C17—O6105.6 (4)C17—C16—N5—C11123.1 (3)
C12—C16—C17—O6−141.5 (3)C12—C16—N5—C113.3 (3)
N6—C22—C23—C24−71.1 (4)N4—C16—N5—C2139.3 (4)
N6—C22—C23—C28110.0 (4)C17—C16—N5—C21−89.1 (3)
C28—C23—C24—C25−3.1 (4)C12—C16—N5—C21151.1 (3)
C22—C23—C24—C25177.9 (3)N6—C21—N5—C1195.4 (3)
C28—C23—C24—Cl4174.9 (2)N6—C21—N5—C16−48.8 (4)
C22—C23—C24—Cl4−4.1 (4)N5—C21—N6—C2054.6 (4)
C23—C24—C25—C261.4 (5)N5—C21—N6—C22−73.1 (3)
Cl4—C24—C25—C26−176.6 (2)N4—C20—N6—C21−54.7 (3)
C24—C25—C26—C271.3 (5)N4—C20—N6—C2273.5 (3)
C24—C25—C26—Cl3−178.6 (2)C23—C22—N6—C21−72.1 (4)
C25—C26—C27—C28−2.1 (5)C23—C22—N6—C20162.0 (3)
Cl3—C26—C27—C28177.8 (3)O3—C13—O4—C14'45.2 (11)
C26—C27—C28—C230.2 (5)C12—C13—O4—C14'−142.4 (10)
C24—C23—C28—C272.3 (5)O3—C13—O4—C14−6.7 (8)
C22—C23—C28—C27−178.7 (3)C12—C13—O4—C14165.7 (5)
C1—C7—N1—C9165.7 (3)C15'—C14'—O4—C13−114.3 (17)
C1—C7—N1—C8−71.1 (4)C15'—C14'—O4—C14−1.5 (17)
N2—C9—N1—C7−174.1 (3)C15—C14—O4—C1389.0 (7)
N2—C9—N1—C861.5 (4)C15—C14—O4—C14'6.2 (9)
N3—C8—N1—C7172.4 (3)O5—C17—O6—C18'−19.0 (14)
N3—C8—N1—C9−62.8 (3)C16—C17—O6—C18'166.3 (13)
O1—C10—N2—C12171.3 (3)O5—C17—O6—C187.4 (10)
N4—C10—N2—C12−12.0 (4)C16—C17—O6—C18−167.3 (8)
O1—C10—N2—C927.5 (5)C19'—C18'—O6—C17141.8 (19)
N4—C10—N2—C9−155.7 (3)C19'—C18'—O6—C1861 (2)
N3—C12—N2—C10−106.4 (3)C19—C18—O6—C17−152.4 (13)
C16—C12—N2—C105.0 (3)C19—C18—O6—C18'−41 (3)
C13—C12—N2—C10131.9 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C19—H19A···O2i0.962.523.380 (11)149
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C19—H19A···O2i0.962.523.380 (11)149
Symmetry codes: (i) x−1/2, −y+1/2, z+1/2.
Acknowledgements top

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

references
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