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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o804.
Published online 2009 March 19. doi:  10.1107/S1600536809009490
PMCID: PMC2968834

Diethyl 6,9,17,20-tetra­bromo-2,13-di­oxo­hexa­cyclo­[10.10.2.03,24.05,10.014,23.016,21]tetra­cosa-5,7,9,16,18,20-hexa­ene-23,24-dicarboxyl­ate

Abstract

In the title mol­ecule, C26H22Br4N4O6, the dihedral angle between the aromatic rings is 30.0 (1)°. One ethyl fragment is disordered between two positions in a 1:1 ratio. The crystal packing exhibits weak inter­molecular C—H(...)O hydrogen bonds and short Br(...)O contacts of 3.349 (6) Å.

Related literature

For applications of glycoluril derivatives, see: Wu et al. (2002 [triangle]); Lee et al. (2003 [triangle]); Rowan et al. (1999 [triangle]); Hof et al. (2002 [triangle]). For details of the synthesis, see: Chen et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o804-scheme1.jpg

Experimental

Crystal data

  • C26H22Br4N4O6
  • M r = 806.12
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o804-efi1.jpg
  • a = 12.3545 (16) Å
  • b = 16.256 (2) Å
  • c = 13.8793 (18) Å
  • β = 93.396 (2)°
  • V = 2782.5 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 5.83 mm−1
  • T = 292 K
  • 0.30 × 0.20 × 0.20 mm

Data collection

  • Bruker SMART 4K CCD area-detector diffractometer
  • Absorption correction: none
  • 18842 measured reflections
  • 6319 independent reflections
  • 3100 reflections with I > 2σ(I)
  • R int = 0.056

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.136
  • S = 1.00
  • 6319 reflections
  • 371 parameters
  • 4 restraints
  • H-atom parameters constrained
  • Δρmax = 0.56 e Å−3
  • Δρmin = −0.45 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: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97 and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809009490/cv2524sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009490/cv2524Isup2.hkl

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

Acknowledgments

The authors are grateful to Xianggao Meng for the data collection.

supplementary crystallographic information

Comment

Glycoluril derivatives have manifested applications in many fields, such as explosives, slow-release fertilizers, crosslinkers, stabilizers of organic compounds agaist photodegratation and reagents in combinational chemistry (Wu et al., 2002). They also play an important role in building block for the preparation of a wide variety of supramolecular assemble, including cucurbit[n] uril homologues (n = 5, 7, 8 and 10) and their derivatives (Lee et al., 2003), molecular clips and baskets (Rowan et al., 1999), and molecular capsules (Hof et al., 2002).

Herein, we present the X-ray crystal structure of the title compound, which is derivated from diethoxycarbonyl glycoluril with dibromo-substituted benzene ring fusing to the side-wall of the molecular clip. The distance between the two carbonyl oxygen atoms (O1—O2) of the glycoluril fragment is 5.498 (7) Å. The crystal packing exhibits weak intermolecular C—H···O hydrogen bonds (Table 2) and short Br···O contacts of 3.349 (6) Å (Table 1).

Experimental

The title compound was synthesized acoording to the procedure reported by Chen et al. (2007). Crystals appropriate for data collection were obtained by slow evaporation of a methanol-chloroform (1:30 v/v) solution at 283 K.

Refinement

All H atoms were initially located in a difference Fourier map and then included in the refinement with constrained bond lengths and isotropic displacement parameters: C—H = 0.93 Å and Uiso(H) = 1.2 Ueq(C) for aromatic H atoms, C—H = 0.97 Å and Uiso(H) = 1.2 Ueq(C) for methylene H atoms, C—H = 0.96 Å and Uiso(H) = 1.5 Ueq(C) for methyl H atoms.

Figures

Fig. 1.
View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented by spheres of arbitrary radius. Only major parts of disordered atoms are shown.

Crystal data

C26H22Br4N4O6F(000) = 1576
Mr = 806.12Dx = 1.924 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -p/2ybcCell parameters from 2976 reflections
a = 12.3545 (16) Åθ = 2.6–20.7°
b = 16.256 (2) ŵ = 5.83 mm1
c = 13.8793 (18) ÅT = 292 K
β = 93.396 (2)°Block, colourless
V = 2782.5 (6) Å30.30 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker SMART 4K CCD area-detector diffractometer3100 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.056
graphiteθmax = 27.5°, θmin = 1.7°
[var phi] and ω scansh = −12→15
18842 measured reflectionsk = −21→21
6319 independent reflectionsl = −17→17

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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0515P)2 + 0.6576P] where P = (Fo2 + 2Fc2)/3
6319 reflections(Δ/σ)max = 0.002
371 parametersΔρmax = 0.56 e Å3
4 restraintsΔρmin = −0.45 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)
Br10.61969 (5)0.07496 (4)0.61428 (4)0.0694 (2)
Br20.25324 (7)−0.20733 (4)0.66394 (5)0.0933 (3)
Br30.55658 (5)0.17500 (5)1.06195 (5)0.0857 (3)
Br40.15555 (6)−0.08284 (4)1.09507 (5)0.0769 (2)
C10.3996 (4)0.0218 (3)0.6329 (3)0.0433 (13)
C20.5079 (4)−0.0014 (4)0.6327 (3)0.0508 (14)
C30.5384 (5)−0.0833 (4)0.6472 (4)0.0653 (17)
H30.6113−0.09790.65000.078*
C40.4613 (6)−0.1412 (4)0.6572 (4)0.0678 (17)
H40.4813−0.19610.66480.081*
C50.3539 (5)−0.1196 (4)0.6564 (4)0.0588 (16)
C60.3195 (4)−0.0390 (3)0.6449 (3)0.0462 (13)
C70.2015 (4)−0.0159 (3)0.6420 (4)0.0526 (14)
H7A0.18140.00810.57950.063*
H7B0.1588−0.06550.64820.063*
C80.3652 (4)0.1101 (3)0.6156 (3)0.0469 (13)
H8A0.42910.14270.60470.056*
H8B0.31800.11250.55730.056*
C90.1494 (4)0.0176 (4)0.8077 (4)0.0449 (13)
C100.3658 (4)0.1654 (3)0.7802 (4)0.0436 (12)
C110.1973 (4)0.1283 (3)0.7108 (3)0.0427 (12)
C120.1199 (5)0.1683 (4)0.6322 (4)0.0649 (17)
C13−0.0687 (11)0.1651 (10)0.5741 (10)0.080 (4)0.541 (11)
H13A−0.11200.11540.56760.096*0.541 (11)
H13B−0.04140.17910.51210.096*0.541 (11)
C14−0.1315 (18)0.2345 (11)0.6141 (16)0.107 (6)0.541 (11)
H14A−0.14310.22400.68080.160*0.541 (11)
H14B−0.20030.23930.57850.160*0.541 (11)
H14C−0.09160.28480.60870.160*0.541 (11)
C150.1837 (4)0.1587 (3)0.8168 (3)0.0441 (13)
C160.1066 (5)0.2326 (4)0.8243 (4)0.0523 (14)
C170.0825 (7)0.3716 (5)0.7716 (7)0.109 (3)
H17A0.08860.39390.70730.131*
H17B0.00710.35750.77850.131*
C180.1129 (7)0.4310 (5)0.8384 (8)0.155 (4)
H18A0.08640.41650.89980.232*
H18B0.08290.48300.81790.232*
H18C0.19050.43480.84410.232*
C190.3251 (4)0.1945 (3)0.9489 (4)0.0485 (13)
H19A0.27100.22920.97640.058*
H19B0.39290.22480.95190.058*
C200.1437 (4)0.0819 (3)0.9678 (3)0.0507 (14)
H20A0.09310.03950.98500.061*
H20B0.11800.13360.99260.061*
C210.2533 (4)0.0630 (3)1.0178 (3)0.0474 (13)
C220.3400 (4)0.1176 (3)1.0107 (3)0.0463 (13)
C230.4376 (4)0.1014 (4)1.0606 (4)0.0548 (15)
C240.4532 (5)0.0293 (4)1.1130 (4)0.0637 (17)
H240.52050.01811.14380.076*
C250.3699 (5)−0.0252 (4)1.1194 (4)0.0612 (16)
H250.3799−0.07381.15430.073*
C260.2702 (4)−0.0073 (4)1.0733 (4)0.0541 (14)
C13'−0.0469 (11)0.2140 (12)0.5903 (17)0.080 (4)0.459 (11)
H13C−0.03120.21140.52270.096*0.459 (11)
H13D−0.03800.27010.61330.096*0.459 (11)
C14'−0.1574 (15)0.1810 (14)0.607 (2)0.107 (6)0.459 (11)
H14D−0.16350.12570.58300.160*0.459 (11)
H14E−0.21140.21490.57430.160*0.459 (11)
H14F−0.16810.18110.67510.160*0.459 (11)
N10.1740 (3)0.0420 (3)0.7170 (3)0.0441 (10)
N20.3088 (3)0.1470 (2)0.6948 (3)0.0433 (10)
N30.1414 (3)0.0873 (3)0.8634 (3)0.0431 (10)
N40.2926 (3)0.1793 (2)0.8489 (3)0.0432 (10)
O10.1336 (3)−0.0520 (2)0.8333 (3)0.0616 (10)
O20.4638 (3)0.1696 (2)0.7916 (3)0.0531 (9)
O30.1497 (4)0.2044 (4)0.5651 (4)0.130 (2)
O40.0196 (3)0.1562 (3)0.6488 (3)0.0963 (17)
O50.1485 (4)0.2968 (3)0.7819 (4)0.0913 (15)
O60.0233 (3)0.2313 (3)0.8621 (3)0.0691 (12)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0487 (4)0.0843 (5)0.0763 (4)0.0001 (3)0.0146 (3)−0.0019 (3)
Br20.1236 (7)0.0512 (5)0.1055 (6)−0.0248 (4)0.0106 (5)−0.0040 (4)
Br30.0615 (5)0.1006 (6)0.0927 (5)−0.0176 (4)−0.0144 (4)−0.0126 (4)
Br40.0786 (5)0.0652 (5)0.0865 (5)−0.0051 (4)0.0010 (4)0.0304 (4)
C10.052 (3)0.042 (3)0.035 (3)0.006 (3)0.001 (2)0.000 (2)
C20.049 (4)0.059 (4)0.045 (3)0.009 (3)0.007 (2)−0.002 (3)
C30.069 (4)0.068 (5)0.059 (3)0.020 (4)0.002 (3)−0.010 (3)
C40.083 (5)0.048 (4)0.073 (4)0.017 (4)0.008 (4)−0.003 (3)
C50.075 (5)0.052 (4)0.049 (3)−0.004 (3)0.003 (3)−0.003 (3)
C60.058 (4)0.041 (4)0.040 (3)−0.004 (3)0.006 (2)−0.002 (2)
C70.050 (4)0.057 (4)0.051 (3)−0.015 (3)−0.001 (3)−0.002 (3)
C80.040 (3)0.052 (4)0.049 (3)0.001 (3)0.011 (2)0.007 (3)
C90.031 (3)0.045 (4)0.057 (3)−0.007 (3)−0.004 (2)0.008 (3)
C100.043 (4)0.027 (3)0.060 (3)−0.002 (2)0.001 (3)0.005 (2)
C110.034 (3)0.040 (3)0.054 (3)0.002 (2)0.005 (2)0.009 (2)
C120.050 (4)0.087 (5)0.058 (4)0.017 (3)0.005 (3)0.025 (3)
C130.042 (7)0.111 (14)0.087 (7)−0.004 (8)−0.006 (5)0.024 (10)
C140.111 (12)0.102 (15)0.104 (8)0.051 (13)−0.020 (8)−0.006 (14)
C150.038 (3)0.039 (3)0.057 (3)0.009 (2)0.010 (2)0.006 (3)
C160.052 (4)0.046 (4)0.059 (3)0.013 (3)0.003 (3)0.010 (3)
C170.100 (6)0.053 (5)0.173 (8)0.035 (5)0.001 (6)0.015 (5)
C180.119 (8)0.082 (7)0.259 (13)0.024 (6)−0.031 (8)−0.033 (8)
C190.041 (3)0.043 (3)0.062 (3)0.000 (3)0.005 (3)−0.006 (3)
C200.043 (3)0.050 (4)0.059 (3)0.005 (3)0.008 (3)0.011 (3)
C210.048 (3)0.048 (4)0.046 (3)0.007 (3)0.005 (2)0.002 (3)
C220.047 (3)0.045 (3)0.048 (3)0.004 (3)0.008 (3)−0.005 (3)
C230.048 (4)0.062 (4)0.053 (3)−0.004 (3)0.000 (3)−0.015 (3)
C240.059 (4)0.086 (5)0.045 (3)0.012 (4)−0.004 (3)0.000 (3)
C250.068 (4)0.062 (4)0.054 (3)0.010 (3)−0.003 (3)0.007 (3)
C260.051 (4)0.059 (4)0.052 (3)0.001 (3)0.004 (3)0.003 (3)
C13'0.042 (7)0.111 (14)0.087 (7)−0.004 (8)−0.006 (5)0.024 (10)
C14'0.111 (12)0.102 (15)0.104 (8)0.051 (13)−0.020 (8)−0.006 (14)
N10.042 (3)0.042 (3)0.048 (3)−0.009 (2)0.0029 (19)0.002 (2)
N20.035 (3)0.040 (3)0.056 (3)0.000 (2)0.010 (2)0.006 (2)
N30.042 (3)0.039 (3)0.049 (2)0.000 (2)0.0075 (19)0.006 (2)
N40.034 (2)0.043 (3)0.053 (3)−0.001 (2)0.004 (2)0.002 (2)
O10.073 (3)0.045 (3)0.067 (2)−0.016 (2)0.001 (2)0.009 (2)
O20.036 (2)0.048 (2)0.076 (2)−0.0035 (17)0.0042 (18)−0.0036 (18)
O30.066 (3)0.193 (6)0.132 (4)0.024 (3)0.012 (3)0.115 (4)
O40.036 (3)0.176 (5)0.076 (3)0.017 (3)−0.003 (2)0.049 (3)
O50.079 (3)0.046 (3)0.152 (4)0.023 (2)0.031 (3)0.031 (3)
O60.052 (3)0.073 (3)0.083 (3)0.019 (2)0.015 (2)0.007 (2)

Geometric parameters (Å, °)

Br1—C21.886 (6)C14—H14B0.9600
Br2—C51.899 (6)C14—H14C0.9600
Br3—C231.895 (6)C15—N41.432 (6)
Br4—C261.912 (6)C15—N31.442 (6)
C1—C21.391 (6)C15—C161.540 (7)
C1—C61.415 (7)C16—O61.183 (6)
C1—C81.513 (7)C16—O51.320 (7)
C2—C31.394 (8)C17—C181.374 (11)
C3—C41.352 (8)C17—O51.466 (7)
C3—H30.9300C17—H17A0.9700
C4—C51.373 (8)C17—H17B0.9700
C4—H40.9300C18—H18A0.9600
C5—C61.382 (7)C18—H18B0.9600
C6—C71.504 (7)C18—H18C0.9600
C7—N11.458 (6)C19—N41.444 (6)
C7—H7A0.9700C19—C221.522 (7)
C7—H7B0.9700C19—H19A0.9700
C8—N21.464 (6)C19—H19B0.9700
C8—H8A0.9700C20—N31.449 (6)
C8—H8B0.9700C20—C211.516 (7)
C9—O11.205 (6)C20—H20A0.9700
C9—N11.370 (6)C20—H20B0.9700
C9—N31.379 (6)C21—C261.386 (7)
C10—O21.213 (5)C21—C221.399 (7)
C10—N41.371 (6)C22—C231.380 (7)
C10—N21.376 (6)C23—C241.387 (8)
C11—N11.437 (6)C24—C251.365 (8)
C11—N21.441 (6)C24—H240.9300
C11—C121.550 (7)C25—C261.386 (7)
C11—C151.571 (7)C25—H250.9300
C12—O31.178 (6)C13'—O41.461 (8)
C12—O41.289 (6)C13'—C14'1.498 (9)
C13—O41.466 (8)C13'—H13C0.9700
C13—C141.496 (9)C13'—H13D0.9700
C13—H13A0.9700C14'—H14D0.9600
C13—H13B0.9700C14'—H14E0.9600
C14—H14A0.9600C14'—H14F0.9600
Br4···O6i3.349 (6)
C2—C1—C6119.4 (5)H17A—C17—H17B107.8
C2—C1—C8121.2 (5)C17—C18—H18A109.5
C6—C1—C8119.3 (5)C17—C18—H18B109.5
C1—C2—C3120.6 (5)H18A—C18—H18B109.5
C1—C2—Br1122.3 (4)C17—C18—H18C109.5
C3—C2—Br1117.0 (4)H18A—C18—H18C109.5
C4—C3—C2119.6 (6)H18B—C18—H18C109.5
C4—C3—H3120.2N4—C19—C22114.8 (4)
C2—C3—H3120.2N4—C19—H19A108.6
C3—C4—C5120.5 (6)C22—C19—H19A108.6
C3—C4—H4119.8N4—C19—H19B108.6
C5—C4—H4119.8C22—C19—H19B108.6
C4—C5—C6122.3 (6)H19A—C19—H19B107.6
C4—C5—Br2116.3 (5)N3—C20—C21115.7 (4)
C6—C5—Br2121.3 (5)N3—C20—H20A108.3
C5—C6—C1117.5 (5)C21—C20—H20A108.3
C5—C6—C7122.1 (5)N3—C20—H20B108.3
C1—C6—C7120.4 (5)C21—C20—H20B108.3
N1—C7—C6114.1 (4)H20A—C20—H20B107.4
N1—C7—H7A108.7C26—C21—C22118.1 (5)
C6—C7—H7A108.7C26—C21—C20121.5 (5)
N1—C7—H7B108.7C22—C21—C20120.4 (5)
C6—C7—H7B108.7C23—C22—C21119.6 (5)
H7A—C7—H7B107.6C23—C22—C19120.8 (5)
N2—C8—C1114.2 (4)C21—C22—C19119.6 (5)
N2—C8—H8A108.7C22—C23—C24121.0 (5)
C1—C8—H8A108.7C22—C23—Br3122.6 (5)
N2—C8—H8B108.7C24—C23—Br3116.4 (4)
C1—C8—H8B108.7C25—C24—C23120.1 (5)
H8A—C8—H8B107.6C25—C24—H24120.0
O1—C9—N1126.2 (5)C23—C24—H24120.0
O1—C9—N3126.0 (5)C24—C25—C26119.1 (6)
N1—C9—N3107.8 (5)C24—C25—H25120.5
O2—C10—N4126.5 (5)C26—C25—H25120.5
O2—C10—N2125.5 (5)C25—C26—C21122.1 (5)
N4—C10—N2108.0 (4)C25—C26—Br4116.0 (4)
N1—C11—N2114.3 (4)C21—C26—Br4121.9 (4)
N1—C11—C12109.5 (4)O4—C13'—C14'99.8 (13)
N2—C11—C12111.0 (4)O4—C13'—H13C111.8
N1—C11—C15102.6 (4)C14'—C13'—H13C111.8
N2—C11—C15103.6 (4)O4—C13'—H13D111.8
C12—C11—C15115.6 (4)C14'—C13'—H13D111.8
O3—C12—O4124.5 (5)H13C—C13'—H13D109.5
O3—C12—C11123.8 (6)C13'—C14'—H14D109.5
O4—C12—C11111.7 (5)C13'—C14'—H14E109.5
O4—C13—C14101.1 (12)H14D—C14'—H14E109.5
O4—C13—H13A111.6C13'—C14'—H14F109.5
C14—C13—H13A111.5H14D—C14'—H14F109.5
O4—C13—H13B111.6H14E—C14'—H14F109.5
C14—C13—H13B111.6C9—N1—C11113.2 (4)
H13A—C13—H13B109.4C9—N1—C7122.9 (4)
N4—C15—N3114.0 (4)C11—N1—C7122.1 (4)
N4—C15—C16111.8 (4)C10—N2—C11111.0 (4)
N3—C15—C16110.9 (4)C10—N2—C8119.6 (4)
N4—C15—C11102.3 (4)C11—N2—C8122.1 (4)
N3—C15—C11103.2 (4)C9—N3—C15111.7 (4)
C16—C15—C11114.2 (4)C9—N3—C20120.9 (4)
O6—C16—O5126.0 (5)C15—N3—C20120.8 (4)
O6—C16—C15125.0 (5)C10—N4—C15113.1 (4)
O5—C16—C15109.0 (5)C10—N4—C19122.6 (4)
C18—C17—O5112.9 (7)C15—N4—C19122.8 (4)
C18—C17—H17A109.0C12—O4—C13'108.5 (8)
O5—C17—H17A109.0C12—O4—C13122.8 (8)
C18—C17—H17B109.0C13'—O4—C1334.4 (8)
O5—C17—H17B109.0C16—O5—C17117.9 (5)
C6—C1—C2—C3−2.1 (7)C22—C21—C26—Br4176.0 (4)
C8—C1—C2—C3−178.9 (5)C20—C21—C26—Br4−2.7 (7)
C6—C1—C2—Br1178.5 (3)O1—C9—N1—C11−175.0 (5)
C8—C1—C2—Br11.7 (6)N3—C9—N1—C117.5 (5)
C1—C2—C3—C43.0 (8)O1—C9—N1—C7−10.2 (8)
Br1—C2—C3—C4−177.6 (4)N3—C9—N1—C7172.3 (4)
C2—C3—C4—C5−2.1 (9)N2—C11—N1—C9111.4 (4)
C3—C4—C5—C60.3 (8)C12—C11—N1—C9−123.3 (5)
C3—C4—C5—Br2176.6 (4)C15—C11—N1—C90.0 (5)
C4—C5—C6—C10.6 (7)N2—C11—N1—C7−53.6 (6)
Br2—C5—C6—C1−175.5 (3)C12—C11—N1—C771.8 (6)
C4—C5—C6—C7178.7 (5)C15—C11—N1—C7−165.0 (4)
Br2—C5—C6—C72.6 (7)C6—C7—N1—C9−86.1 (6)
C2—C1—C6—C50.3 (7)C6—C7—N1—C1177.4 (6)
C8—C1—C6—C5177.2 (4)O2—C10—N2—C11166.6 (5)
C2—C1—C6—C7−177.9 (4)N4—C10—N2—C11−14.4 (5)
C8—C1—C6—C7−0.9 (7)O2—C10—N2—C815.8 (7)
C5—C6—C7—N1120.7 (5)N4—C10—N2—C8−165.2 (4)
C1—C6—C7—N1−61.2 (6)N1—C11—N2—C10−97.3 (5)
C2—C1—C8—N2−120.9 (5)C12—C11—N2—C10138.3 (5)
C6—C1—C8—N262.2 (6)C15—C11—N2—C1013.6 (5)
N1—C11—C12—O3−122.6 (7)N1—C11—N2—C852.7 (6)
N2—C11—C12—O34.5 (9)C12—C11—N2—C8−71.8 (6)
C15—C11—C12—O3122.1 (7)C15—C11—N2—C8163.5 (4)
N1—C11—C12—O456.7 (6)C1—C8—N2—C1071.0 (6)
N2—C11—C12—O4−176.1 (5)C1—C8—N2—C11−76.5 (6)
C15—C11—C12—O4−58.6 (7)O1—C9—N3—C15169.9 (5)
N1—C11—C15—N4111.6 (4)N1—C9—N3—C15−12.6 (5)
N2—C11—C15—N4−7.6 (5)O1—C9—N3—C2018.3 (7)
C12—C11—C15—N4−129.3 (5)N1—C9—N3—C20−164.2 (4)
N1—C11—C15—N3−7.0 (4)N4—C15—N3—C9−98.0 (5)
N2—C11—C15—N3−126.3 (4)C16—C15—N3—C9134.8 (4)
C12—C11—C15—N3112.1 (5)C11—C15—N3—C912.1 (5)
N1—C11—C15—C16−127.5 (5)N4—C15—N3—C2053.5 (6)
N2—C11—C15—C16113.3 (5)C16—C15—N3—C20−73.6 (5)
C12—C11—C15—C16−8.3 (7)C11—C15—N3—C20163.7 (4)
N4—C15—C16—O6−129.1 (6)C21—C20—N3—C973.2 (6)
N3—C15—C16—O6−0.7 (8)C21—C20—N3—C15−75.8 (6)
C11—C15—C16—O6115.4 (6)O2—C10—N4—C15−172.1 (5)
N4—C15—C16—O550.9 (6)N2—C10—N4—C159.0 (5)
N3—C15—C16—O5179.3 (4)O2—C10—N4—C19−5.5 (8)
C11—C15—C16—O5−64.7 (6)N2—C10—N4—C19175.5 (4)
N3—C20—C21—C26−118.9 (5)N3—C15—N4—C10110.2 (5)
N3—C20—C21—C2262.5 (6)C16—C15—N4—C10−123.1 (5)
C26—C21—C22—C23−1.8 (7)C11—C15—N4—C10−0.5 (5)
C20—C21—C22—C23176.9 (5)N3—C15—N4—C19−56.3 (6)
C26—C21—C22—C19178.8 (4)C16—C15—N4—C1970.4 (6)
C20—C21—C22—C19−2.6 (7)C11—C15—N4—C19−167.0 (4)
N4—C19—C22—C23122.6 (5)C22—C19—N4—C10−87.6 (6)
N4—C19—C22—C21−58.0 (6)C22—C19—N4—C1577.6 (6)
C21—C22—C23—C243.9 (8)O3—C12—O4—C13'−17.0 (15)
C19—C22—C23—C24−176.7 (5)C11—C12—O4—C13'163.7 (12)
C21—C22—C23—Br3−175.9 (4)O3—C12—O4—C1318.0 (13)
C19—C22—C23—Br33.5 (7)C11—C12—O4—C13−161.4 (8)
C22—C23—C24—C25−2.9 (9)C14'—C13'—O4—C12171.1 (16)
Br3—C23—C24—C25176.9 (4)C14'—C13'—O4—C1349.6 (18)
C23—C24—C25—C26−0.2 (9)C14—C13—O4—C12−116.9 (15)
C24—C25—C26—C212.4 (9)C14—C13—O4—C13'−43 (2)
C24—C25—C26—Br4−175.1 (4)O6—C16—O5—C17−6.4 (10)
C22—C21—C26—C25−1.4 (8)C15—C16—O5—C17173.6 (6)
C20—C21—C26—C25180.0 (5)C18—C17—O5—C16102.1 (9)

Symmetry codes: (i) −x, −y, −z+2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C4—H4···O2ii0.932.363.278 (7)172
C19—H19A···O3iii0.972.273.227 (7)169
C25—H25···O2iv0.932.563.309 (7)138

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2524).

References

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