organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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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

aKey Laboratory of Pesticides and Chemical Biology of the Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
*Correspondence e-mail: wuhanshe@126.com

(Received 7 August 2009; accepted 18 August 2009; online 26 August 2009)

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[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.]). For a related structure, see: Wu et al. (2002[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.]). For ring-puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For bond-length data, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • C20H20Br2N4O7

  • Mr = 588.22

  • Monoclinic, P 21 /c

  • 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)

  • Rint = 0.097

Refinement
  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C19—H19B⋯O2i 0.97 2.51 3.353 (4) 146
C17—H17A⋯Br1ii 0.97 2.94 3.625 (10) 129
C8—H8B⋯O2iii 0.97 2.39 3.324 (4) 161
Symmetry codes: (i) -x, -y, -z+1; (ii) [-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Comment top

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 [ϕ = -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.

Related literature top

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

Experimental top

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 top

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.

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: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] 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.
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 top
Crystal data top
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 top
Bruker SMART 4K CCD area-detector
diffractometer
2983 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.097
Graphite monochromatorθmax = 27.0°, θmin = 2.1°
ϕ and ω scansh = 1515
18344 measured reflectionsk = 1919
4736 independent reflectionsl = 1413
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H-atom parameters constrained
S = 0.91 w = 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 = 0.59 e Å3
Crystal data top
C20H20Br2N4O7V = 2179.5 (3) Å3
Mr = 588.22Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.4679 (10) ŵ = 3.77 mm1
b = 15.1505 (13) ÅT = 292 K
c = 11.5383 (10) Å0.30 × 0.20 × 0.20 mm
β = 90.189 (1)°
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
2983 reflections with I > 2σ(I)
18344 measured reflectionsRint = 0.097
4736 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05030 restraints
wR(F2) = 0.134H-atom parameters constrained
S = 0.91Δρmax = 1.00 e Å3
4736 reflectionsΔρmin = 0.59 e Å3
349 parameters
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 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) top
xyzUiso*/UeqOcc. (<1)
Br10.39306 (3)0.14276 (3)0.75601 (4)0.06508 (19)
Br20.31776 (4)0.30716 (4)0.57266 (4)0.0716 (2)
O10.01869 (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)
C10.0639 (3)0.1581 (2)0.7972 (3)0.0368 (8)
C20.1724 (3)0.1369 (2)0.8074 (3)0.0429 (9)
H20.19370.09380.85990.052*
C30.2483 (3)0.1793 (3)0.7405 (3)0.0434 (9)
C40.2182 (3)0.2441 (3)0.6642 (3)0.0453 (9)
C50.1106 (3)0.2646 (2)0.6516 (3)0.0407 (8)
H50.09030.30770.59880.049*
C60.0329 (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*
H7B0.02060.07250.92490.051*
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)
H14F0.38040.01401.10010.198*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)
H17A0.43370.19460.61280.060*0.51 (2)
H17B0.46930.14080.72340.060*0.51 (2)
C17'0.4760 (10)0.0973 (16)0.6529 (15)0.082 (6)0.49 (2)
H17C0.47870.13860.71710.098*0.49 (2)
H17D0.51640.04490.67350.098*0.49 (2)
C180.5452 (7)0.0986 (11)0.5752 (14)0.066 (4)0.51 (2)
H18A0.52650.09410.49470.079*0.51 (2)
H18B0.60640.13660.58380.079*0.51 (2)
H18C0.56220.04100.60490.079*0.51 (2)
C18'0.5196 (12)0.1389 (17)0.5435 (14)0.096 (6)0.49 (2)
H18D0.47780.19010.52420.115*0.49 (2)
H18E0.59300.15590.55580.115*0.49 (2)
H18F0.51580.09710.48110.115*0.49 (2)
C190.1211 (3)0.1018 (2)0.5829 (3)0.0459 (9)
H19A0.18120.14140.57070.055*
H19B0.05840.13750.59970.055*
C200.1918 (3)0.0019 (3)0.4536 (3)0.0435 (9)
H20A0.17730.03460.38300.052*
H20B0.25410.03500.44030.052*
Atomic displacement parameters (Å2) top
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, º) top
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—C31.2 (5)N3—C9—N1—C7168.9 (3)
C7—C1—C2—C3179.5 (3)N2—C11—N1—C994.8 (3)
C1—C2—C3—C41.0 (5)C12—C11—N1—C9140.8 (3)
C1—C2—C3—Br1177.5 (3)C15—C11—N1—C914.6 (3)
C2—C3—C4—C52.2 (6)N2—C11—N1—C756.0 (4)
Br1—C3—C4—C5176.2 (3)C12—C11—N1—C768.4 (4)
C2—C3—C4—Br2178.3 (3)C15—C11—N1—C7165.4 (3)
Br1—C3—C4—Br23.2 (5)C1—C7—N1—C972.5 (4)
C3—C4—C5—C61.1 (6)C1—C7—N1—C1176.0 (4)
Br2—C4—C5—C6179.4 (3)O2—C10—N2—C11173.0 (3)
C4—C5—C6—C11.2 (5)N4—C10—N2—C119.2 (4)
C4—C5—C6—C8178.6 (3)O2—C10—N2—C86.8 (5)
C2—C1—C6—C52.3 (5)N4—C10—N2—C8175.4 (3)
C7—C1—C6—C5178.5 (3)N1—C11—N2—C10107.8 (3)
C2—C1—C6—C8177.5 (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—N162.0 (4)C12—C11—N2—C868.3 (4)
C5—C6—C8—N2120.8 (3)C15—C11—N2—C8168.0 (3)
C1—C6—C8—N259.0 (4)C6—C8—N2—C1086.8 (4)
N2—C11—C12—O328.4 (5)C6—C8—N2—C1178.2 (4)
N1—C11—C12—O3155.6 (4)O1—C9—N3—C1927.9 (5)
C15—C11—C12—O386.2 (5)N1—C9—N3—C19156.0 (3)
N2—C11—C12—O4142.1 (5)O1—C9—N3—C15170.8 (3)
N1—C11—C12—O414.9 (6)N1—C9—N3—C1513.1 (4)
C15—C11—C12—O4103.3 (5)O7—C19—N3—C993.6 (4)
N2—C11—C12—O4'169.3 (9)O7—C19—N3—C1547.3 (4)
N1—C11—C12—O4'42.0 (9)N4—C15—N3—C9107.8 (3)
C15—C11—C12—O4'76.1 (9)C16—C15—N3—C9127.6 (3)
O3—C12—O4—C1310.4 (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—C1988.1 (4)
C12—O4—C13—C14173.3 (7)C11—C15—N3—C19148.2 (3)
O3—C12—O4'—C13'10.1 (19)O2—C10—N4—C15169.0 (3)
O4—C12—O4'—C13'86 (2)N2—C10—N4—C1513.2 (3)
C11—C12—O4'—C13'171.6 (13)O2—C10—N4—C2032.8 (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—C10136.3 (3)
C12—C11—C15—N4112.2 (3)C11—C15—N4—C1011.6 (3)
N2—C11—C15—N3111.9 (3)N3—C15—N4—C2037.5 (4)
N1—C11—C15—N36.1 (3)C16—C15—N4—C2086.4 (4)
C12—C11—C15—N3130.0 (3)C11—C15—N4—C20148.9 (3)
N2—C11—C15—C16128.0 (3)O7—C20—N4—C1083.8 (4)
N1—C11—C15—C16114.0 (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—C17163.9 (5)
N3—C15—C16—O5117.0 (5)O5—C16—O6—C17'6.2 (13)
C11—C15—C16—O50.5 (6)C15—C16—O6—C17'177.0 (11)
N4—C15—C16—O665.6 (4)C18—C17—O6—C1693.3 (16)
N3—C15—C16—O659.7 (4)C18—C17—O6—C17'48.3 (18)
C11—C15—C16—O6176.3 (3)C18'—C17'—O6—C16153.5 (19)
O1—C9—N1—C11166.1 (3)C18'—C17'—O6—C1762.7 (17)
N3—C9—N1—C1117.8 (4)N4—C20—O7—C1959.7 (4)
O1—C9—N1—C715.0 (5)N3—C19—O7—C2058.3 (4)
Hydrogen-bond geometry (Å, º) top
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, y1/2, z+3/2; (iii) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC20H20Br2N4O7
Mr588.22
Crystal system, space groupMonoclinic, P21/c
Temperature (K)292
a, b, c (Å)12.4679 (10), 15.1505 (13), 11.5383 (10)
β (°) 90.189 (1)
V3)2179.5 (3)
Z4
Radiation typeMo Kα
µ (mm1)3.77
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART 4K CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
18344, 4736, 2983
Rint0.097
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.134, 0.91
No. of reflections4736
No. of parameters349
No. of restraints30
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.00, 0.59

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19B···O2i0.972.513.353 (4)145.8
C17—H17A···Br1ii0.972.943.625 (10)128.9
C8—H8B···O2iii0.972.393.324 (4)160.6
Symmetry codes: (i) x, y, z+1; (ii) x, y1/2, z+3/2; (iii) x, y+1/2, z+1/2.
 

Acknowledgements

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

References

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