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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): o2252.
Published online 2009 August 26. doi:  10.1107/S160053680903284X
PMCID: PMC2969905

Diethyl 7,8-dibromo-4,11-dioxo-11b,11c-dihydro-5H,10H-2-oxa-3a,4a,10a,11a-tetra­azabenz[f]indeno[2,1,7,7a-ija]azulene-11b,11c-dicarboxyl­ate

Abstract

The title compound, C20H20Br2N4O7, is an inter­mediate for mol­ecular clips. The seven- and six-membered rings have chair conformations, while the five-membered rings adopt envelope conformations. In the crystal structure, weak C—H(...)O and C—H(...)Br inter­actions link the mol­ecules into a three-dimensional network. The eth­oxy and ethyl groups are disordered over two orientations, with occupancy ratios of 0.735 (16):0.265 (16) and 0.51 (2):0.49 (2), respectively.

Related literature

For general background, see: Burnett et al. (2003 [triangle]). For a related structure, see: Wu et al. (2002 [triangle]). For ring-puckering parameters, see: Cremer & Pople (1975 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2252-scheme1.jpg

Experimental

Crystal data

  • C20H20Br2N4O7
  • M r = 588.22
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2252-efi1.jpg
  • a = 12.4679 (10) Å
  • b = 15.1505 (13) Å
  • c = 11.5383 (10) Å
  • β = 90.189 (1)°
  • V = 2179.5 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 3.77 mm−1
  • T = 292 K
  • 0.30 × 0.20 × 0.20 mm

Data collection

  • Bruker SMART 4K CCD area-detector diffractometer
  • Absorption correction: none
  • 18344 measured reflections
  • 4736 independent reflections
  • 2983 reflections with I > 2σ(I)
  • R int = 0.097

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.134
  • S = 0.91
  • 4736 reflections
  • 349 parameters
  • 30 restraints
  • H-atom parameters constrained
  • Δρmax = 1.00 e Å−3
  • Δρmin = −0.59 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [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: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680903284X/hk2753sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903284X/hk2753Isup2.hkl

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

Acknowledgments

The authors are grateful to the Central China Normal University, and Professor Wu Anxin for financial support.

supplementary crystallographic information

Comment

Diethoxycarbonyl glycoluril bearing a range of electron withdrawing functional groups on its convex face is an important building block for both molecular and supramolecular chemistry (Burnett et al., 2003). The title compound derived from diethoxycarbonyl glycoluril is an important intermediate for methylene-bridged glycoluril dimers, and we report herein its crystal structure.

In the molecule of the title compound, (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Ring A (C1-C6) is, of course, planar. The seven-membered ring B (N1/N2/C1/C6-C8/c11) is not planar, having total puckering amplitude, QT, of 2.878 (2) Å (Cremer & Pople, 1975), and resembles chair conformation. Rings C (N1/N3/C9/C11/C15) and D (N2/N4/C10/C11/C15) adopt envelope conformations with atoms N1 and N4 displaced by -0.208 (3) and -0.174 (3) Å from the planes of the other ring atoms, respectively, while ring E (O7/N3/N4/C15/C19/C20) is not planar, having total puckering amplitude, QT, of 0.429 (2) Å and adopts chair conformation [[var phi] = -90.18 (3) and θ = 91.16 (3) °] (Cremer & Pople, 1975).

In the crystal structure, weak C-H···O and C-H···Br interactions link the molecules into a three-dimensional network (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental

The title compound was synthesized according to a literature method (Wu et al., 2002). Crystals suitable for X-ray analysis were obtained by slow evaporation of a dichloride methane solution at 283 K.

Refinement

H atoms were positioned geometrically, with C-H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C). The ethoxy and ethyl groups attached at C12 and O6, respectively, are disordered over two orientations. During the refinement process, the disordered O4, C13, C14, H13A, H13B, H14A, H14B, H14C and O4', C13', C14', H13C, H13D, H14D, H14E, H14F atoms were refined with occupancies of 0.735 (16) and 0.265 (16), while C17, C18, H17A, H17B, H18A, H18B, H18C and C17', C18', H17C, H17D, H18D, H18E, H18F atoms were refined with occupancies of 0.51 (2) and 0.49 (2), respectively, by applying some restraints.

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
A partial packing diagram. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

Crystal data

C20H20Br2N4O7F(000) = 1176
Mr = 588.22Dx = 1.793 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5213 reflections
a = 12.4679 (10) Åθ = 2.2–26.1°
b = 15.1505 (13) ŵ = 3.77 mm1
c = 11.5383 (10) ÅT = 292 K
β = 90.189 (1)°Block, colorless
V = 2179.5 (3) Å30.30 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker SMART 4K CCD area-detector diffractometer2983 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.097
graphiteθmax = 27.0°, θmin = 2.1°
[var phi] and ω scansh = −15→15
18344 measured reflectionsk = −19→19
4736 independent reflectionsl = −14→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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H-atom parameters constrained
S = 0.91w = 1/[σ2(Fo2) + (0.08P)2] where P = (Fo2 + 2Fc2)/3
4736 reflections(Δ/σ)max < 0.001
349 parametersΔρmax = 1.00 e Å3
30 restraintsΔρmin = −0.58 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)
Br1−0.39306 (3)0.14276 (3)0.75601 (4)0.06508 (19)
Br2−0.31776 (4)0.30716 (4)0.57266 (4)0.0716 (2)
O1−0.01869 (19)−0.05766 (16)0.7742 (2)0.0470 (7)
O20.1247 (2)0.18343 (17)0.4670 (2)0.0461 (6)
O30.3227 (3)0.2018 (2)0.8002 (3)0.0737 (10)
O40.2543 (5)0.1138 (5)0.9343 (4)0.0491 (16)0.735 (16)
O4'0.2838 (13)0.0817 (11)0.9206 (11)0.053 (4)0.265 (16)
O50.3918 (3)0.0190 (3)0.7638 (4)0.1048 (15)
O60.3624 (2)−0.0744 (3)0.6229 (3)0.0823 (11)
O70.10231 (19)−0.05214 (17)0.4804 (2)0.0465 (6)
N10.0940 (2)0.05941 (18)0.8063 (2)0.0342 (6)
N20.1467 (2)0.16772 (18)0.6633 (2)0.0344 (6)
N30.1438 (2)−0.04468 (18)0.6808 (3)0.0375 (7)
N40.2148 (2)0.06373 (19)0.5477 (2)0.0362 (7)
C1−0.0639 (3)0.1581 (2)0.7972 (3)0.0368 (8)
C2−0.1724 (3)0.1369 (2)0.8074 (3)0.0429 (9)
H2−0.19370.09380.85990.052*
C3−0.2483 (3)0.1793 (3)0.7405 (3)0.0434 (9)
C4−0.2182 (3)0.2441 (3)0.6642 (3)0.0453 (9)
C5−0.1106 (3)0.2646 (2)0.6516 (3)0.0407 (8)
H5−0.09030.30770.59880.049*
C6−0.0329 (3)0.2218 (2)0.7163 (3)0.0368 (8)
C70.0170 (3)0.1112 (3)0.8718 (3)0.0423 (9)
H7A0.05550.15450.91770.051*
H7B−0.02060.07250.92490.051*
C80.0838 (3)0.2443 (2)0.6985 (3)0.0381 (8)
H8A0.08950.28970.63960.046*
H8B0.11310.26790.77000.046*
C90.0625 (3)−0.0180 (2)0.7541 (3)0.0358 (8)
C100.1571 (3)0.1427 (2)0.5517 (3)0.0345 (8)
C110.1813 (3)0.1016 (2)0.7450 (3)0.0352 (8)
C120.2663 (3)0.1435 (3)0.8275 (3)0.0487 (10)
C130.3325 (7)0.1493 (6)1.0189 (6)0.070 (3)0.735 (16)
H13A0.32120.21211.03030.084*0.735 (16)
H13B0.40520.14020.99170.084*0.735 (16)
C13'0.3735 (18)0.0999 (19)1.0039 (17)0.081 (7)0.265 (16)
H13C0.37520.16211.02360.097*0.265 (16)
H13D0.44170.08410.96950.097*0.265 (16)
C140.3146 (8)0.1006 (8)1.1289 (7)0.106 (4)0.735 (16)
H14A0.24060.10551.15070.128*0.735 (16)
H14B0.35900.12531.18880.128*0.735 (16)
H14C0.33270.03951.11820.128*0.735 (16)
C14'0.354 (3)0.045 (3)1.112 (2)0.165 (17)0.265 (16)
H14D0.27800.04231.12720.198*0.265 (16)
H14E0.38990.07101.17690.198*0.265 (16)
H14F0.3804−0.01401.10010.198*0.265 (16)
C150.2217 (2)0.0256 (2)0.6629 (3)0.0344 (8)
C160.3359 (3)−0.0087 (3)0.6886 (4)0.0492 (10)
C170.4520 (7)−0.1364 (8)0.6416 (14)0.050 (3)0.51 (2)
H17A0.4337−0.19460.61280.060*0.51 (2)
H17B0.4693−0.14080.72340.060*0.51 (2)
C17'0.4760 (10)−0.0973 (16)0.6529 (15)0.082 (6)0.49 (2)
H17C0.4787−0.13860.71710.098*0.49 (2)
H17D0.5164−0.04490.67350.098*0.49 (2)
C180.5452 (7)−0.0986 (11)0.5752 (14)0.066 (4)0.51 (2)
H18A0.5265−0.09410.49470.079*0.51 (2)
H18B0.6064−0.13660.58380.079*0.51 (2)
H18C0.5622−0.04100.60490.079*0.51 (2)
C18'0.5196 (12)−0.1389 (17)0.5435 (14)0.096 (6)0.49 (2)
H18D0.4778−0.19010.52420.115*0.49 (2)
H18E0.5930−0.15590.55580.115*0.49 (2)
H18F0.5158−0.09710.48110.115*0.49 (2)
C190.1211 (3)−0.1018 (2)0.5829 (3)0.0459 (9)
H19A0.1812−0.14140.57070.055*
H19B0.0584−0.13750.59970.055*
C200.1918 (3)0.0019 (3)0.4536 (3)0.0435 (9)
H20A0.17730.03460.38300.052*
H20B0.2541−0.03500.44030.052*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0421 (2)0.0827 (4)0.0705 (3)−0.0127 (2)0.0010 (2)−0.0028 (2)
Br20.0526 (3)0.0970 (4)0.0652 (3)0.0130 (2)−0.0028 (2)0.0176 (3)
O10.0421 (14)0.0383 (14)0.0606 (18)−0.0069 (11)0.0073 (12)0.0001 (12)
O20.0572 (15)0.0466 (15)0.0344 (15)0.0013 (12)−0.0013 (12)0.0038 (12)
O30.070 (2)0.074 (2)0.077 (2)−0.0353 (17)−0.0222 (17)0.0031 (18)
O40.045 (3)0.067 (4)0.035 (3)0.001 (2)−0.016 (2)−0.003 (2)
O4'0.031 (6)0.088 (9)0.039 (6)0.006 (6)−0.004 (5)−0.006 (6)
O50.058 (2)0.129 (4)0.127 (3)0.027 (2)−0.050 (2)−0.051 (3)
O60.0556 (18)0.107 (3)0.084 (2)0.0454 (18)−0.0168 (17)−0.028 (2)
O70.0470 (14)0.0474 (15)0.0451 (16)0.0019 (12)−0.0088 (12)−0.0125 (12)
N10.0360 (14)0.0362 (15)0.0303 (15)−0.0013 (12)0.0016 (12)−0.0024 (13)
N20.0391 (15)0.0336 (15)0.0305 (16)−0.0023 (12)0.0009 (12)−0.0027 (12)
N30.0387 (15)0.0336 (16)0.0401 (17)−0.0002 (12)−0.0002 (13)−0.0040 (13)
N40.0375 (14)0.0399 (16)0.0311 (16)0.0030 (12)−0.0010 (12)−0.0026 (13)
C10.0437 (19)0.0347 (19)0.0320 (19)0.0005 (15)0.0056 (15)−0.0098 (15)
C20.049 (2)0.042 (2)0.038 (2)−0.0012 (17)0.0076 (17)−0.0068 (17)
C30.0372 (18)0.047 (2)0.046 (2)−0.0059 (16)0.0066 (16)−0.0110 (18)
C40.0426 (19)0.050 (2)0.043 (2)0.0057 (17)−0.0009 (16)−0.0114 (18)
C50.049 (2)0.0367 (19)0.037 (2)0.0009 (16)0.0057 (16)−0.0064 (16)
C60.0452 (19)0.0327 (18)0.033 (2)−0.0001 (15)0.0026 (15)−0.0093 (15)
C70.050 (2)0.046 (2)0.032 (2)−0.0033 (17)0.0086 (16)−0.0054 (17)
C80.0440 (18)0.0330 (18)0.037 (2)−0.0029 (15)0.0020 (16)−0.0044 (15)
C90.0354 (17)0.0367 (19)0.035 (2)0.0035 (15)−0.0008 (14)0.0037 (15)
C100.0327 (16)0.0355 (19)0.035 (2)−0.0065 (14)−0.0005 (14)−0.0015 (16)
C110.0332 (16)0.0411 (19)0.0311 (19)−0.0037 (14)−0.0038 (14)−0.0035 (15)
C120.044 (2)0.060 (3)0.042 (2)−0.0079 (19)−0.0106 (18)−0.006 (2)
C130.071 (4)0.069 (5)0.070 (5)−0.005 (4)−0.039 (4)−0.001 (4)
C13'0.092 (11)0.080 (11)0.071 (10)−0.014 (8)−0.004 (8)−0.021 (8)
C140.119 (7)0.133 (9)0.066 (6)0.014 (7)−0.041 (5)0.008 (5)
C14'0.166 (19)0.165 (19)0.165 (19)0.001 (10)−0.012 (10)−0.006 (10)
C150.0315 (16)0.0384 (19)0.0334 (19)0.0004 (14)−0.0028 (14)−0.0037 (15)
C160.0362 (19)0.060 (3)0.051 (3)0.0025 (18)−0.0016 (18)0.007 (2)
C170.045 (5)0.046 (6)0.059 (8)0.004 (4)−0.002 (4)−0.004 (5)
C17'0.049 (8)0.081 (12)0.115 (11)0.036 (7)−0.037 (8)−0.039 (10)
C180.043 (5)0.089 (10)0.065 (9)0.014 (5)0.009 (5)0.011 (7)
C18'0.057 (8)0.104 (14)0.127 (15)0.035 (8)−0.016 (8)−0.013 (10)
C190.045 (2)0.037 (2)0.056 (3)−0.0023 (16)0.0008 (18)−0.0112 (19)
C200.048 (2)0.048 (2)0.034 (2)0.0065 (17)0.0040 (16)−0.0097 (17)

Geometric parameters (Å, °)

Br1—C31.896 (3)C13'—C14'1.522 (10)
Br2—C41.887 (4)C13'—H13C0.9700
O4—C131.479 (6)C13'—H13D0.9700
O4'—C13'1.498 (10)C14—H14A0.9600
C1—C21.396 (5)C14—H14B0.9600
C1—C61.399 (5)C14—H14C0.9600
C1—C71.503 (5)C14'—H14D0.9600
C2—C31.378 (5)C14'—H14E0.9600
C2—H20.9300C14'—H14F0.9600
C3—C41.372 (6)C15—N41.451 (4)
C4—C51.386 (5)C15—N31.457 (4)
C5—C61.382 (5)C15—C161.544 (5)
C5—H50.9300C16—O51.188 (5)
C6—C81.509 (5)C16—O61.294 (5)
C7—N11.453 (4)C17—O61.475 (8)
C7—H7A0.9700C17—C181.507 (9)
C7—H7B0.9700C17—H17A0.9700
C8—N21.459 (4)C17—H17B0.9700
C8—H8A0.9700C17'—O61.497 (8)
C8—H8B0.9700C17'—C18'1.514 (10)
C9—O11.199 (4)C17'—H17C0.9700
C9—N11.376 (4)C17'—H17D0.9700
C9—N31.383 (4)C18—H18A0.9600
C10—O21.223 (4)C18—H18B0.9600
C10—N21.349 (4)C18—H18C0.9600
C10—N41.396 (4)C18'—H18D0.9600
C11—N21.440 (4)C18'—H18E0.9600
C11—N11.450 (4)C18'—H18F0.9600
C11—C121.558 (5)C19—O71.421 (5)
C11—C151.575 (5)C19—N31.451 (5)
C12—O31.173 (5)C19—H19A0.9700
C12—O41.321 (6)C19—H19B0.9700
C12—O4'1.441 (10)C20—O71.419 (4)
C13—C141.485 (8)C20—N41.462 (5)
C13—H13A0.9700C20—H20A0.9700
C13—H13B0.9700C20—H20B0.9700
C12—O4—C13114.5 (5)O3—C12—C11123.3 (4)
C12—O4'—C13'118.0 (14)O4—C12—C11110.7 (4)
C16—O6—C17126.8 (7)O4'—C12—C11107.0 (6)
C16—O6—C17'106.6 (6)O4—C13—C14106.4 (5)
C20—O7—C19111.1 (3)O4—C13—H13A110.4
C9—N1—C11112.1 (3)C14—C13—H13A110.4
C9—N1—C7120.0 (3)O4—C13—H13B110.4
C11—N1—C7120.9 (3)C14—C13—H13B110.4
C10—N2—C11113.5 (3)H13A—C13—H13B108.6
C10—N2—C8122.9 (3)O4'—C13'—C14'107.5 (13)
C11—N2—C8122.1 (3)O4'—C13'—H13C110.2
C9—N3—C19120.6 (3)C14'—C13'—H13C110.2
C9—N3—C15111.4 (3)O4'—C13'—H13D110.2
C19—N3—C15117.0 (3)C14'—C13'—H13D110.2
C10—N4—C15109.9 (3)H13C—C13'—H13D108.5
C10—N4—C20118.3 (3)C13'—C14'—H14D109.5
C15—N4—C20115.9 (3)C13'—C14'—H14E109.5
C2—C1—C6119.0 (3)H14D—C14'—H14E109.5
C2—C1—C7119.5 (3)C13'—C14'—H14F109.5
C6—C1—C7121.5 (3)H14D—C14'—H14F109.5
C3—C2—C1120.6 (4)H14E—C14'—H14F109.5
C3—C2—H2119.7N4—C15—N3112.6 (3)
C1—C2—H2119.7N4—C15—C16111.2 (3)
C4—C3—C2120.3 (3)N3—C15—C16109.9 (3)
C4—C3—Br1122.1 (3)N4—C15—C11104.0 (3)
C2—C3—Br1117.6 (3)N3—C15—C11103.6 (2)
C3—C4—C5119.7 (4)C16—C15—C11115.3 (3)
C3—C4—Br2122.7 (3)O5—C16—O6123.3 (4)
C5—C4—Br2117.6 (3)O5—C16—C15124.0 (4)
C6—C5—C4121.0 (4)O6—C16—C15112.6 (3)
C6—C5—H5119.5O6—C17—C18105.6 (7)
C4—C5—H5119.5O6—C17—H17A110.6
C5—C6—C1119.3 (3)C18—C17—H17A110.6
C5—C6—C8119.7 (3)O6—C17—H17B110.6
C1—C6—C8121.0 (3)C18—C17—H17B110.6
N1—C7—C1113.6 (3)H17A—C17—H17B108.8
N1—C7—H7A108.9O6—C17'—C18'104.3 (7)
C1—C7—H7A108.9O6—C17'—H17C110.9
N1—C7—H7B108.9C18'—C17'—H17C110.9
C1—C7—H7B108.9O6—C17'—H17D110.9
H7A—C7—H7B107.7C18'—C17'—H17D110.9
N2—C8—C6112.2 (3)H17C—C17'—H17D108.9
N2—C8—H8A109.2C17'—C18'—H18D109.5
C6—C8—H8A109.2C17'—C18'—H18E109.5
N2—C8—H8B109.2H18D—C18'—H18E109.5
C6—C8—H8B109.2C17'—C18'—H18F109.5
H8A—C8—H8B107.9H18D—C18'—H18F109.5
O1—C9—N1125.6 (3)H18E—C18'—H18F109.5
O1—C9—N3126.3 (3)O7—C19—N3111.3 (3)
N1—C9—N3107.9 (3)O7—C19—H19A109.4
O2—C10—N2126.0 (3)N3—C19—H19A109.4
O2—C10—N4125.1 (3)O7—C19—H19B109.4
N2—C10—N4108.9 (3)N3—C19—H19B109.4
N2—C11—N1113.7 (3)H19A—C19—H19B108.0
N2—C11—C12108.6 (3)O7—C20—N4111.1 (3)
N1—C11—C12113.1 (3)O7—C20—H20A109.4
N2—C11—C15102.2 (3)N4—C20—H20A109.4
N1—C11—C15102.3 (3)O7—C20—H20B109.4
C12—C11—C15116.6 (3)N4—C20—H20B109.4
O3—C12—O4125.3 (4)H20A—C20—H20B108.0
O3—C12—O4'127.0 (7)
C6—C1—C2—C3−1.2 (5)N3—C9—N1—C7168.9 (3)
C7—C1—C2—C3179.5 (3)N2—C11—N1—C994.8 (3)
C1—C2—C3—C4−1.0 (5)C12—C11—N1—C9−140.8 (3)
C1—C2—C3—Br1177.5 (3)C15—C11—N1—C9−14.6 (3)
C2—C3—C4—C52.2 (6)N2—C11—N1—C7−56.0 (4)
Br1—C3—C4—C5−176.2 (3)C12—C11—N1—C768.4 (4)
C2—C3—C4—Br2−178.3 (3)C15—C11—N1—C7−165.4 (3)
Br1—C3—C4—Br23.2 (5)C1—C7—N1—C9−72.5 (4)
C3—C4—C5—C6−1.1 (6)C1—C7—N1—C1176.0 (4)
Br2—C4—C5—C6179.4 (3)O2—C10—N2—C11173.0 (3)
C4—C5—C6—C1−1.2 (5)N4—C10—N2—C11−9.2 (4)
C4—C5—C6—C8178.6 (3)O2—C10—N2—C86.8 (5)
C2—C1—C6—C52.3 (5)N4—C10—N2—C8−175.4 (3)
C7—C1—C6—C5−178.5 (3)N1—C11—N2—C10−107.8 (3)
C2—C1—C6—C8−177.5 (3)C12—C11—N2—C10125.4 (3)
C7—C1—C6—C81.7 (5)C15—C11—N2—C101.7 (3)
C2—C1—C7—N1117.2 (4)N1—C11—N2—C858.5 (4)
C6—C1—C7—N1−62.0 (4)C12—C11—N2—C8−68.3 (4)
C5—C6—C8—N2−120.8 (3)C15—C11—N2—C8168.0 (3)
C1—C6—C8—N259.0 (4)C6—C8—N2—C1086.8 (4)
N2—C11—C12—O3−28.4 (5)C6—C8—N2—C11−78.2 (4)
N1—C11—C12—O3−155.6 (4)O1—C9—N3—C1927.9 (5)
C15—C11—C12—O386.2 (5)N1—C9—N3—C19−156.0 (3)
N2—C11—C12—O4142.1 (5)O1—C9—N3—C15170.8 (3)
N1—C11—C12—O414.9 (6)N1—C9—N3—C15−13.1 (4)
C15—C11—C12—O4−103.3 (5)O7—C19—N3—C993.6 (4)
N2—C11—C12—O4'169.3 (9)O7—C19—N3—C15−47.3 (4)
N1—C11—C12—O4'42.0 (9)N4—C15—N3—C9−107.8 (3)
C15—C11—C12—O4'−76.1 (9)C16—C15—N3—C9127.6 (3)
O3—C12—O4—C13−10.4 (9)C11—C15—N3—C93.9 (3)
O4'—C12—O4—C1392.9 (17)N4—C15—N3—C1936.5 (4)
C11—C12—O4—C13179.4 (5)C16—C15—N3—C19−88.1 (4)
C12—O4—C13—C14−173.3 (7)C11—C15—N3—C19148.2 (3)
O3—C12—O4'—C13'10.1 (19)O2—C10—N4—C15−169.0 (3)
O4—C12—O4'—C13'−86 (2)N2—C10—N4—C1513.2 (3)
C11—C12—O4'—C13'171.6 (13)O2—C10—N4—C20−32.8 (5)
C12—O4'—C13'—C14'162 (2)N2—C10—N4—C20149.4 (3)
N2—C11—C15—N45.9 (3)N3—C15—N4—C1099.8 (3)
N1—C11—C15—N4123.9 (3)C16—C15—N4—C10−136.3 (3)
C12—C11—C15—N4−112.2 (3)C11—C15—N4—C10−11.6 (3)
N2—C11—C15—N3−111.9 (3)N3—C15—N4—C20−37.5 (4)
N1—C11—C15—N36.1 (3)C16—C15—N4—C2086.4 (4)
C12—C11—C15—N3130.0 (3)C11—C15—N4—C20−148.9 (3)
N2—C11—C15—C16128.0 (3)O7—C20—N4—C10−83.8 (4)
N1—C11—C15—C16−114.0 (3)O7—C20—N4—C1549.8 (4)
C12—C11—C15—C169.8 (4)O5—C16—O6—C1712.8 (8)
N4—C15—C16—O5117.6 (5)C15—C16—O6—C17−163.9 (5)
N3—C15—C16—O5−117.0 (5)O5—C16—O6—C17'−6.2 (13)
C11—C15—C16—O5−0.5 (6)C15—C16—O6—C17'177.0 (11)
N4—C15—C16—O6−65.6 (4)C18—C17—O6—C16−93.3 (16)
N3—C15—C16—O659.7 (4)C18—C17—O6—C17'−48.3 (18)
C11—C15—C16—O6176.3 (3)C18'—C17'—O6—C16−153.5 (19)
O1—C9—N1—C11−166.1 (3)C18'—C17'—O6—C1762.7 (17)
N3—C9—N1—C1117.8 (4)N4—C20—O7—C19−59.7 (4)
O1—C9—N1—C7−15.0 (5)N3—C19—O7—C2058.3 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C19—H19B···O2i0.972.513.353 (4)146
C17—H17A···Br1ii0.972.943.625 (10)129
C8—H8B···O2iii0.972.393.324 (4)161

Symmetry codes: (i) −x, −y, −z+1; (ii) −x, y−1/2, −z+3/2; (iii) x, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2753).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Bruker (2001). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Burnett, C. A., Lagona, J., Wu, A., Shaw, J. A., Coady, D., Fettinger, J. C., Day, A. I. & Isaacs, L. (2003). Tetrahedron, 59, 1961–1970.
  • Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc.97, 1354–1358.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [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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