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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o289.
Published online 2010 January 9. doi:  10.1107/S1600536810000097
PMCID: PMC2979957

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

Abstract

In the title mol­ecule, C24H31N5O6, 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 inter­molecular non-classical C—H(...)O hydrogen bonds and π–π inter­actions between benzene rings [centroid–centroid distances = 3.836 (5) Å].

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-66-0o289-scheme1.jpg

Experimental

Crystal data

  • C24H31N5O6
  • M r = 485.54
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o289-efi1.jpg
  • 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 [triangle]); cell refinement: SAINT (Bruker, 1999 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

The authors are grateful to Central China Normal University for financial support.

supplementary crystallographic information

Comment

As a continuation of our structural studies of glucoluril derivatives (Wang et al., 2006; Chen et al., 2007), herein we report the crystal structure of the title compound, (I) (Fig. 1). In the title compound, a benzene ring is fused to one seven-membered ring, which binds two of the N atoms from separate rings of the glycoluril system, and the other two N atoms are linked to tert-butylamine by two methylene group.

Experimental

The title compound was synthesized according to the reported literature (Wu et al., 2002). Crystals of (I) suitable for X-ray diffraction were grown by slow evaporation of a dichloromethane-methanol (1:2) solution of the title compound under 293 K.

Refinement

All H-atoms were positioned geometrically in idealized positions and constrained to ride on their parent atoms, with d(C—H) = 0.97 Å, Uiso = 1.2Ueq (C) for CH2 and d(C—H) = 0.96 Å, Uiso = 1.5Ueq (C) for CH3 atoms. The two ethyl group were treated as disordered over two positions.The occupancies of the disordered positions refined to 0.58 (13)/0.42 (13) and 0.56 (12)/0.44 (12), respectively.

Figures

Fig. 1.
A view of (I), showing the atom-labelling scheme, with displacement ellipsoids drawn at the 30% probability level. Only major parts of disordered atoms are shown. H atoms omitted for clarity.

Crystal data

C24H31N5O6Z = 2
Mr = 485.54F(000) = 516
Triclinic, P1Dx = 1.314 Mg m3
a = 10.7133 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.1013 (15) ÅCell parameters from 2728 reflections
c = 11.3352 (15) Åθ = 2.3–23.3°
α = 100.493 (2)°µ = 0.10 mm1
β = 105.438 (2)°T = 292 K
γ = 102.445 (2)°Block, colourless
V = 1227.2 (3) Å30.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer2734 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.051
graphiteθmax = 25.0°, θmin = 1.9°
phi and ω scansh = −12→12
9853 measured reflectionsk = −13→13
4253 independent reflectionsl = −13→13

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.195H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.116P)2] where P = (Fo2 + 2Fc2)/3
4253 reflections(Δ/σ)max < 0.001
397 parametersΔρmax = 0.46 e Å3
99 restraintsΔρmin = −0.27 e Å3

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)
C10.2330 (3)−0.0629 (3)0.5732 (4)0.0707 (9)
C20.1387 (4)−0.1323 (3)0.4603 (5)0.0946 (12)
H20.1646−0.14740.38810.114*
C30.0032 (5)−0.1810 (4)0.4517 (7)0.131 (2)
H3−0.0605−0.22760.37450.157*
C4−0.0332 (6)−0.1590 (6)0.5575 (10)0.141 (3)
H4−0.1225−0.19150.55250.169*
C50.0599 (6)−0.0892 (5)0.6724 (7)0.1203 (18)
H50.0326−0.07520.74390.144*
C60.1936 (4)−0.0398 (3)0.6825 (4)0.0825 (11)
C70.2936 (5)0.0298 (3)0.8120 (4)0.0916 (12)
H7A0.24470.03880.87230.110*
H7B0.3532−0.02200.83740.110*
C80.3760 (3)−0.0180 (2)0.5746 (3)0.0634 (8)
H8A0.4280−0.06690.61930.076*
H8B0.3772−0.03720.48800.076*
C90.4226 (3)0.2080 (2)0.5675 (2)0.0450 (6)
C100.3472 (3)0.2665 (3)0.8592 (3)0.0641 (8)
C110.4844 (3)0.1701 (2)0.7674 (2)0.0576 (7)
C120.5931 (4)0.1179 (3)0.8426 (3)0.0844 (11)
C130.7589 (10)0.0161 (11)0.8247 (10)0.138 (4)0.58 (13)
H13A0.7778−0.03990.75940.166*0.58
H13B0.7242−0.03520.87570.166*0.58
C140.8840 (12)0.1122 (12)0.9046 (13)0.184 (6)0.58 (13)
H14A0.90790.17460.85990.276*0.58
H14B0.95480.07190.92530.276*0.58
H14C0.87120.15330.98090.276*0.58
C150.5263 (3)0.3179 (2)0.7817 (2)0.0504 (7)
C160.6759 (4)0.3861 (3)0.8485 (3)0.0730 (9)
C170.8800 (10)0.4862 (14)0.8238 (14)0.188 (5)0.56 (12)
H17A0.92080.45840.89740.225*0.56
H17B0.92020.46340.75880.225*0.56
C180.8945 (16)0.6226 (16)0.856 (2)0.190 (8)0.56
H18A0.86940.65050.78020.286*0.56
H18B0.98650.66740.90460.286*0.56
H18C0.83700.63990.90550.286*0.56
C190.4409 (3)0.4385 (2)0.6278 (2)0.0519 (7)
H19A0.39840.42540.53770.062*
H19B0.51960.51190.65590.062*
C200.4129 (3)0.4808 (2)0.8311 (2)0.0569 (7)
H20A0.49420.55140.86040.068*
H20B0.35320.50120.87790.068*
C210.2878 (3)0.5689 (3)0.6669 (3)0.0642 (8)
C220.1716 (4)0.5641 (4)0.7200 (4)0.0937 (11)
H22A0.10860.48080.68650.141*
H22B0.12720.62670.69650.141*
H22C0.20530.58180.81060.141*
C230.3910 (4)0.7005 (3)0.7234 (4)0.0996 (12)
H23A0.42860.71340.81320.149*
H23B0.34720.76540.70680.149*
H23C0.46160.70510.68570.149*
C240.2300 (4)0.5452 (4)0.5232 (3)0.0966 (12)
H24A0.30190.55050.48710.145*
H24B0.18480.60850.50400.145*
H24C0.16710.46200.48850.145*
C13'0.8049 (12)0.0858 (17)0.867 (2)0.169 (8)0.42 (13)
H13C0.82640.12810.95580.203*0.42
H13D0.88370.11420.84190.203*0.42
C14'0.7753 (15)−0.0522 (15)0.8527 (12)0.165 (6)0.42 (13)
H14D0.7121−0.07800.89570.248*0.42
H14E0.8571−0.07350.88850.248*0.42
H14F0.7374−0.09570.76450.248*0.42
C17'0.8558 (11)0.5710 (11)0.8799 (13)0.095 (3)0.44 (12)
H17C0.91760.52590.85750.113*0.44
H17D0.87930.59630.97130.113*0.44
C18'0.8578 (12)0.6842 (12)0.8253 (13)0.127 (5)0.44 (12)
H18D0.83800.65710.73530.190*0.44
H18E0.94540.74440.86190.190*0.44
H18F0.79130.72360.84350.190*0.44
N10.4438 (2)0.11805 (18)0.63279 (19)0.0510 (6)
N20.3746 (3)0.1548 (2)0.8183 (2)0.0725 (8)
N30.4818 (2)0.32668 (18)0.65159 (18)0.0479 (5)
N40.4467 (2)0.3659 (2)0.85387 (19)0.0550 (6)
N50.3465 (2)0.46257 (18)0.69526 (18)0.0503 (6)
O10.36756 (19)0.18819 (16)0.45526 (17)0.0599 (5)
O20.2539 (3)0.2773 (2)0.8978 (2)0.0899 (8)
O30.5872 (17)0.0875 (14)0.9359 (8)0.135 (5)0.58 (13)
O40.6596 (7)0.0723 (8)0.7670 (7)0.098 (3)0.58 (13)
O50.7302 (5)0.3777 (6)0.9524 (3)0.0774 (14)0.56 (12)
O60.7316 (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)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.068 (2)0.0460 (16)0.113 (3)0.0248 (15)0.034 (2)0.0346 (17)
C20.074 (3)0.0547 (19)0.145 (4)0.0146 (18)0.015 (3)0.033 (2)
C30.086 (4)0.074 (3)0.220 (7)0.019 (2)0.015 (4)0.060 (4)
C40.075 (3)0.089 (3)0.287 (9)0.031 (3)0.067 (5)0.092 (5)
C50.102 (4)0.084 (3)0.235 (6)0.047 (3)0.100 (4)0.089 (4)
C60.081 (2)0.0564 (18)0.151 (4)0.0345 (18)0.068 (3)0.059 (2)
C70.130 (3)0.073 (2)0.116 (3)0.041 (2)0.082 (3)0.051 (2)
C80.069 (2)0.0480 (15)0.082 (2)0.0226 (14)0.0330 (16)0.0182 (14)
C90.0465 (15)0.0489 (14)0.0454 (15)0.0169 (11)0.0220 (12)0.0110 (12)
C100.094 (2)0.0698 (18)0.0530 (17)0.0396 (17)0.0424 (17)0.0273 (14)
C110.076 (2)0.0577 (15)0.0579 (18)0.0337 (14)0.0313 (15)0.0261 (13)
C120.119 (3)0.083 (2)0.068 (2)0.054 (2)0.026 (2)0.035 (2)
C130.142 (7)0.122 (7)0.149 (7)0.104 (6)0.001 (5)0.015 (6)
C140.126 (9)0.213 (12)0.166 (10)0.093 (9)−0.029 (8)−0.008 (8)
C150.0614 (18)0.0584 (15)0.0383 (14)0.0277 (13)0.0170 (13)0.0143 (12)
C160.070 (2)0.082 (2)0.071 (2)0.0379 (19)0.0151 (19)0.0211 (18)
C170.133 (8)0.218 (10)0.195 (9)0.029 (7)0.039 (7)0.052 (8)
C180.122 (13)0.208 (17)0.178 (15)0.043 (12)−0.013 (10)−0.010 (12)
C190.0669 (18)0.0457 (13)0.0460 (15)0.0161 (12)0.0200 (13)0.0153 (11)
C200.0750 (19)0.0546 (15)0.0469 (16)0.0286 (14)0.0211 (14)0.0119 (12)
C210.077 (2)0.0558 (16)0.0696 (19)0.0343 (15)0.0210 (16)0.0244 (14)
C220.097 (3)0.101 (3)0.112 (3)0.060 (2)0.044 (2)0.040 (2)
C230.121 (3)0.0509 (18)0.133 (3)0.0342 (19)0.037 (3)0.0299 (19)
C240.128 (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)
N10.0648 (14)0.0454 (11)0.0523 (13)0.0213 (10)0.0270 (11)0.0156 (10)
N20.108 (2)0.0633 (14)0.0836 (17)0.0394 (14)0.0650 (16)0.0379 (13)
N30.0620 (14)0.0450 (12)0.0406 (12)0.0193 (10)0.0175 (10)0.0132 (10)
N40.0752 (16)0.0602 (13)0.0400 (12)0.0315 (12)0.0226 (11)0.0169 (10)
N50.0635 (14)0.0456 (11)0.0454 (12)0.0202 (10)0.0181 (11)0.0133 (9)
O10.0706 (13)0.0613 (11)0.0430 (11)0.0178 (9)0.0145 (10)0.0078 (9)
O20.122 (2)0.0931 (16)0.1017 (17)0.0523 (14)0.0815 (16)0.0441 (13)
O30.172 (10)0.171 (9)0.107 (7)0.076 (7)0.047 (6)0.111 (7)
O40.086 (4)0.109 (5)0.080 (4)0.054 (4)−0.009 (3)−0.002 (3)
O50.072 (3)0.115 (4)0.0313 (19)0.032 (3)−0.0084 (19)0.015 (2)
O60.070 (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)

Geometric parameters (Å, °)

C1—C21.367 (5)C16—O61.243 (6)
C1—C61.410 (5)C16—O6'1.293 (6)
C1—C81.500 (4)C17—C181.455 (17)
C2—C31.406 (7)C17—O61.483 (10)
C2—H20.9300C17—H17A0.9700
C3—C41.354 (8)C17—H17B0.9700
C3—H30.9300C18—H18A0.9600
C4—C51.378 (8)C18—H18B0.9600
C4—H40.9300C18—H18C0.9600
C5—C61.385 (6)C19—N31.449 (3)
C5—H50.9300C19—N51.460 (3)
C6—C71.514 (5)C19—H19A0.9700
C7—N21.448 (4)C19—H19B0.9700
C7—H7A0.9700C20—N41.447 (3)
C7—H7B0.9700C20—N51.469 (3)
C8—N11.468 (3)C20—H20A0.9700
C8—H8A0.9700C20—H20B0.9700
C8—H8B0.9700C21—N51.498 (3)
C9—O11.207 (3)C21—C221.516 (4)
C9—N11.369 (3)C21—C241.530 (4)
C9—N31.381 (3)C21—C231.534 (5)
C10—O21.212 (3)C22—H22A0.9600
C10—N21.363 (4)C22—H22B0.9600
C10—N41.382 (4)C22—H22C0.9600
C11—N21.434 (3)C23—H23A0.9600
C11—N11.439 (3)C23—H23B0.9600
C11—C121.536 (4)C23—H23C0.9600
C11—C151.571 (4)C24—H24A0.9600
C12—O31.180 (7)C24—H24B0.9600
C12—O3'1.189 (9)C24—H24C0.9600
C12—O41.350 (6)C13'—O4'1.418 (8)
C12—O4'1.352 (7)C13'—C14'1.465 (14)
C13—O41.418 (7)C13'—H13C0.9700
C13—C141.463 (12)C13'—H13D0.9700
C13—H13A0.9700C14'—H14D0.9600
C13—H13B0.9700C14'—H14E0.9600
C14—H14A0.9600C14'—H14F0.9600
C14—H14B0.9600C17'—O6'1.450 (10)
C14—H14C0.9600C17'—C18'1.497 (17)
C15—N41.445 (3)C17'—H17C0.9700
C15—N31.452 (3)C17'—H17D0.9700
C15—C161.529 (4)C18'—H18D0.9600
C16—O5'1.170 (9)C18'—H18E0.9600
C16—O51.197 (4)C18'—H18F0.9600
C2—C1—C6119.5 (3)N3—C19—N5109.90 (18)
C2—C1—C8117.4 (3)N3—C19—H19A109.7
C6—C1—C8123.1 (3)N5—C19—H19A109.7
C1—C2—C3120.9 (5)N3—C19—H19B109.7
C1—C2—H2119.5N5—C19—H19B109.7
C3—C2—H2119.5H19A—C19—H19B108.2
C4—C3—C2119.0 (6)N4—C20—N5110.0 (2)
C4—C3—H3120.5N4—C20—H20A109.7
C2—C3—H3120.5N5—C20—H20A109.7
C3—C4—C5121.2 (5)N4—C20—H20B109.7
C3—C4—H4119.4N5—C20—H20B109.7
C5—C4—H4119.4H20A—C20—H20B108.2
C4—C5—C6120.6 (5)N5—C21—C22107.9 (2)
C4—C5—H5119.7N5—C21—C24108.7 (2)
C6—C5—H5119.7C22—C21—C24107.6 (3)
C5—C6—C1118.8 (5)N5—C21—C23112.8 (2)
C5—C6—C7118.7 (4)C22—C21—C23109.6 (3)
C1—C6—C7122.4 (3)C24—C21—C23110.1 (3)
N2—C7—C6114.3 (3)C21—C22—H22A109.5
N2—C7—H7A108.7C21—C22—H22B109.5
C6—C7—H7A108.7H22A—C22—H22B109.5
N2—C7—H7B108.7C21—C22—H22C109.5
C6—C7—H7B108.7H22A—C22—H22C109.5
H7A—C7—H7B107.6H22B—C22—H22C109.5
N1—C8—C1116.0 (2)C21—C23—H23A109.5
N1—C8—H8A108.3C21—C23—H23B109.5
C1—C8—H8A108.3H23A—C23—H23B109.5
N1—C8—H8B108.3C21—C23—H23C109.5
C1—C8—H8B108.3H23A—C23—H23C109.5
H8A—C8—H8B107.4H23B—C23—H23C109.5
O1—C9—N1126.4 (2)C21—C24—H24A109.5
O1—C9—N3125.6 (2)C21—C24—H24B109.5
N1—C9—N3107.9 (2)H24A—C24—H24B109.5
O2—C10—N2125.9 (3)C21—C24—H24C109.5
O2—C10—N4125.6 (3)H24A—C24—H24C109.5
N2—C10—N4108.5 (2)H24B—C24—H24C109.5
N2—C11—N1113.7 (2)O4'—C13'—C14'113.2 (14)
N2—C11—C12108.8 (2)O4'—C13'—H13C108.9
N1—C11—C12113.5 (2)C14'—C13'—H13C108.9
N2—C11—C15102.01 (19)O4'—C13'—H13D108.9
N1—C11—C15102.94 (17)C14'—C13'—H13D108.9
C12—C11—C15115.4 (3)H13C—C13'—H13D107.8
O3—C12—O3'24.2 (17)C13'—C14'—H14D109.5
O3—C12—O4124.6 (9)C13'—C14'—H14E109.5
O3'—C12—O4124.5 (10)H14D—C14'—H14E109.5
O3—C12—O4'126.2 (9)C13'—C14'—H14F109.5
O3'—C12—O4'114.3 (12)H14D—C14'—H14F109.5
O4—C12—O4'25.0 (6)H14E—C14'—H14F109.5
O3—C12—C11121.6 (8)O6'—C17'—C18'103.2 (9)
O3'—C12—C11125.3 (10)O6'—C17'—H17C111.1
O4—C12—C11109.8 (4)C18'—C17'—H17C111.1
O4'—C12—C11111.9 (5)O6'—C17'—H17D111.1
O4—C13—C14111.9 (9)C18'—C17'—H17D111.1
O4—C13—H13A109.2H17C—C17'—H17D109.1
C14—C13—H13A109.2C17'—C18'—H18D109.5
O4—C13—H13B109.2C17'—C18'—H18E109.5
C14—C13—H13B109.2H18D—C18'—H18E109.5
H13A—C13—H13B107.9C17'—C18'—H18F109.5
N4—C15—N3111.76 (19)H18D—C18'—H18F109.5
N4—C15—C16109.9 (2)H18E—C18'—H18F109.5
N3—C15—C16112.5 (2)C9—N1—C11111.99 (19)
N4—C15—C11104.0 (2)C9—N1—C8121.2 (2)
N3—C15—C11102.7 (2)C11—N1—C8121.5 (2)
C16—C15—C11115.6 (2)C10—N2—C11113.5 (2)
O5'—C16—O544.5 (12)C10—N2—C7124.6 (3)
O5'—C16—O695.8 (12)C11—N2—C7121.6 (2)
O5—C16—O6126.7 (5)C9—N3—C19122.0 (2)
O5'—C16—O6'115.4 (9)C9—N3—C15111.98 (19)
O5—C16—O6'116.8 (5)C19—N3—C15118.26 (19)
O6—C16—O6'39.5 (5)C10—N4—C15110.4 (2)
O5'—C16—C15127.3 (8)C10—N4—C20118.8 (2)
O5—C16—C15120.3 (4)C15—N4—C20115.72 (19)
O6—C16—C15112.1 (4)C19—N5—C20108.5 (2)
O6'—C16—C15114.4 (4)C19—N5—C21114.05 (19)
C18—C17—O6102.7 (10)C20—N5—C21112.94 (19)
C18—C17—H17A111.2C12—O4—C13115.0 (7)
O6—C17—H17A111.2C16—O6—C17118.2 (7)
C18—C17—H17B111.2C12—O4'—C13'114.1 (9)
O6—C17—H17B111.2C16—O6'—C17'121.3 (7)
H17A—C17—H17B109.1
C6—C1—C2—C3−0.1 (4)N4—C10—N2—C7179.1 (3)
C8—C1—C2—C3178.2 (3)N1—C11—N2—C10−110.4 (3)
C1—C2—C3—C4−0.4 (6)C12—C11—N2—C10122.1 (3)
C2—C3—C4—C50.5 (7)C15—C11—N2—C10−0.3 (3)
C3—C4—C5—C60.0 (6)N1—C11—N2—C763.1 (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—C7173.2 (3)
C2—C1—C6—C50.5 (4)C6—C7—N2—C1097.0 (4)
C8—C1—C6—C5−177.6 (3)C6—C7—N2—C11−75.7 (4)
C2—C1—C6—C7176.5 (3)O1—C9—N3—C1925.1 (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—C15173.8 (2)
C1—C6—C7—N255.6 (4)N1—C9—N3—C15−9.4 (3)
C2—C1—C8—N1129.5 (3)N5—C19—N3—C998.0 (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—C9124.6 (2)
C15—C11—C12—O3105.0 (10)C11—C15—N3—C9−0.3 (3)
N2—C11—C12—O3'−37.6 (14)N4—C15—N3—C1938.8 (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—C19149.8 (2)
N2—C11—C12—O4149.7 (5)O2—C10—N4—C15−169.4 (3)
N1—C11—C12—O422.0 (5)N2—C10—N4—C1512.9 (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—C20150.0 (2)
N1—C11—C12—O4'48.7 (6)N3—C15—N4—C1097.5 (2)
C15—C11—C12—O4'−69.7 (6)C16—C15—N4—C10−136.9 (2)
N2—C11—C15—N47.6 (3)C11—C15—N4—C10−12.6 (3)
N1—C11—C15—N4125.7 (2)N3—C15—N4—C20−41.0 (3)
C12—C11—C15—N4−110.1 (3)C16—C15—N4—C2084.6 (3)
N2—C11—C15—N3−109.0 (2)C11—C15—N4—C20−151.1 (2)
N1—C11—C15—N39.1 (2)N5—C20—N4—C10−80.5 (3)
C12—C11—C15—N3133.2 (2)N5—C20—N4—C1554.3 (3)
N2—C11—C15—C16128.1 (2)N3—C19—N5—C2058.7 (3)
N1—C11—C15—C16−113.8 (2)N3—C19—N5—C21−174.4 (2)
C12—C11—C15—C1610.4 (3)N4—C20—N5—C19−62.2 (3)
N4—C15—C16—O5'115.1 (16)N4—C20—N5—C21170.3 (2)
N3—C15—C16—O5'−119.8 (16)C22—C21—N5—C19168.0 (3)
C11—C15—C16—O5'−2.3 (16)C24—C21—N5—C1951.7 (3)
N4—C15—C16—O561.5 (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—C20176.2 (2)
N4—C15—C16—O6−128.4 (6)C23—C21—N5—C2053.8 (3)
N3—C15—C16—O6−3.2 (6)O3—C12—O4—C13−19.6 (14)
C11—C15—C16—O6114.3 (6)O3'—C12—O4—C139.9 (17)
N4—C15—C16—O6'−85.3 (5)O4'—C12—O4—C1383.1 (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—C1116.2 (3)O5—C16—O6—C17−3.6 (13)
O1—C9—N1—C8−12.6 (4)O6'—C16—O6—C1785.1 (10)
N3—C9—N1—C8170.6 (2)C15—C16—O6—C17−173.0 (8)
N2—C11—N1—C993.9 (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—C864.5 (3)C11—C12—O4'—C13'174.9 (10)
C15—C11—N1—C8−170.0 (2)C14'—C13'—O4'—C1274.8 (19)
C1—C8—N1—C9−80.3 (3)O5'—C16—O6'—C17'−19.1 (18)
C1—C8—N1—C1171.8 (3)O5—C16—O6'—C17'30.7 (11)
O2—C10—N2—C11174.7 (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—C71.4 (5)C18'—C17'—O6'—C16−179.2 (9)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C22—H22C···O5i0.962.523.474 (5)174
C13—H13A···O1ii0.972.543.288 (11)134

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2681).

References

  • Bruker (1997). SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (1999). SAINT Bruker AXS Inc., Madison, Wisconsin,USA.
  • Chen, Y., She, N., Meng, X., Yin, G., Wu, A. & Isaacs, L. (2007). Org. Lett.9, 1899–1902. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, Z., Zhou, B., Chen, Y., Yin, G., Li, Y., Wu, A. & Isaacs, L. (2006). J. Org. Chem.71, 4502–4508. [PubMed]
  • Wu, A., Chakraborty, A., Witt, D., Lagona, J., Damkaci, F., Ofori, M. A., Chiles, J. K., Fettinger, J. C. & Isaacs, L. (2002). J. Org. Chem.67, 5817–5830. [PubMed]

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