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In the title compound, C28H32N6O6, the dihedral angles between the two fused five-membered rings in the glycoluril unit and between the two terminal benzene rings are 71.78 (2) and 66.76 (2)°, respectively. The mol­ecules are connected mainly by van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054803/ng2358sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054803/ng2358Isup2.hkl
Contains datablock I

CCDC reference: 672846

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.057
  • wR factor = 0.136
  • Data-to-parameter ratio = 15.9

checkCIF/PLATON results

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Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.58 Ratio PLAT301_ALERT_3_C Main Residue Disorder ......................... 2.00 Perc. PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C28
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Since Mock and co-workers first characterized the chemical nature and structure of cucurbit[6]uril (Freeman et al., 1981), many clip molecules based on glycoluril as supramolecular receptor have been reported (Rowan et al., 1999; Li et al., 2006; Wang et al., 2006; Chen et al., 2007; Hu et al., 2007; She et al., 2007). As a continuation of our previous studies in this area, we herein report the crystal structure of the title compound, (I), a new type of receptor based on glycoluril (Fig. 1). Selected bond lengths and angles are listed in Table 1. Two six-membered rings (N1—C8—N2 –C12—N3—C9 and N4—C16—N5—C21—N6—C20) both adopt the chair conformation. The dihedral angle between the two fused five-membered rings in the glycoluril unit is 71.78 (2) °. The crystal packing is mainly governed by van der Waals forces.

Related literature top

For the preparation of the title compound, see: Yin et al. (2006). For the structure of cucurbit[6]uril, see Freeman et al. (1981). For literature on clip molecules based on glycoluril, see Chen et al. (2007); Hu et al. (2007); Li et al. (2006); Rowan et al. (1999); She et al. (2007); Wang et al. (2006).

Experimental top

The title compound was synthesized according to the reported literature (Yin et al., 2006). Crystals of (I) suitable for X-ray diffraction were grown by slow evaporation of a dichloromethane-methanol (4:1) solution of the title compound under ambient conditions.

Refinement top

One of the ethyl groups (C15) was found to be disordered over two orientations. The occupancies of the disordered positions C15/C15' refined to 0.64 (2):0.36 (2). All H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and refined as riding, allowing for free rotation of the methyl groups. The constraint Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) (methyl C) was applied.

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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. A view of (I), showing the atom-labelling scheme, with displacement ellipsoids drawn at the 30% probability level.
Diethyl 2,6-bis(3-methylphenyl)-4,8-dioxo-2,6,3a,4a,7a,8a- hexaazaperhydrocyclopenta[def]fluorene-8 b,8c-dicarboxylate top
Crystal data top
C28H32N6O6F(000) = 2320
Mr = 548.60Dx = 1.350 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ac2abCell parameters from 4426 reflections
a = 17.8591 (13) Åθ = 2.6–21.8°
b = 15.4533 (11) ŵ = 0.10 mm1
c = 19.5649 (14) ÅT = 292 K
V = 5399.6 (7) Å3Block, colorless
Z = 80.30 × 0.20 × 0.10 mm
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
4406 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.050
Graphite monochromatorθmax = 27.0°, θmin = 2.0°
ϕ and ω scansh = 2222
30333 measured reflectionsk = 1919
5874 independent reflectionsl = 1624
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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0501P)2 + 2.134P]
where P = (Fo2 + 2Fc2)/3
5874 reflections(Δ/σ)max = 0.001
370 parametersΔρmax = 0.21 e Å3
1 restraintΔρmin = 0.19 e Å3
Crystal data top
C28H32N6O6V = 5399.6 (7) Å3
Mr = 548.60Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 17.8591 (13) ŵ = 0.10 mm1
b = 15.4533 (11) ÅT = 292 K
c = 19.5649 (14) Å0.30 × 0.20 × 0.10 mm
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
4406 reflections with I > 2σ(I)
30333 measured reflectionsRint = 0.050
5874 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0571 restraint
wR(F2) = 0.136H-atom parameters constrained
S = 1.05Δρmax = 0.21 e Å3
5874 reflectionsΔρmin = 0.19 e Å3
370 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)
C10.13577 (17)0.19168 (16)0.46245 (14)0.0655 (8)
H1A0.11420.18800.50730.098*
H1B0.18730.17410.46430.098*
H1C0.10890.15440.43180.098*
C20.13103 (13)0.28371 (14)0.43719 (11)0.0462 (6)
C30.07028 (14)0.33474 (17)0.45309 (14)0.0568 (7)
H30.03170.31210.47960.068*
C40.06592 (14)0.41882 (17)0.43031 (14)0.0579 (7)
H40.02450.45240.44150.069*
C50.12232 (12)0.45357 (15)0.39119 (12)0.0465 (6)
H50.11880.51040.37580.056*
C60.18480 (11)0.40391 (13)0.37455 (10)0.0360 (5)
C70.18868 (12)0.31908 (14)0.39802 (11)0.0406 (5)
H70.23030.28550.38740.049*
C80.29814 (12)0.38598 (13)0.30343 (11)0.0378 (5)
H8A0.33180.36580.33890.045*
H8B0.27450.33600.28260.045*
C90.27758 (12)0.51778 (13)0.36519 (10)0.0372 (5)
H9A0.24000.55480.38570.045*
H9B0.31100.49820.40100.045*
C100.31559 (11)0.43743 (13)0.18532 (11)0.0349 (5)
C110.28227 (11)0.62743 (12)0.27600 (10)0.0314 (4)
C120.37140 (11)0.51700 (12)0.27303 (10)0.0322 (4)
C130.44683 (11)0.50352 (14)0.30994 (11)0.0386 (5)
C140.57290 (13)0.45747 (18)0.29232 (14)0.0607 (7)
H14A0.58530.50600.32170.073*0.64 (2)
H14B0.60690.45830.25370.073*0.64 (2)
H14C0.60710.48650.26140.073*0.36 (2)
H14D0.57810.48340.33720.073*0.36 (2)
C150.5831 (5)0.3757 (6)0.3308 (8)0.081 (3)0.64 (2)
H15A0.55190.37630.37070.122*0.64 (2)
H15B0.63460.37020.34430.122*0.64 (2)
H15C0.56950.32770.30230.122*0.64 (2)
C15'0.5909 (11)0.3650 (8)0.2959 (12)0.081 (3)0.36 (2)
H15D0.55550.33640.32520.122*0.36 (2)
H15E0.64040.35770.31400.122*0.36 (2)
H15F0.58840.34030.25100.122*0.36 (2)
C160.37500 (11)0.56958 (12)0.20477 (10)0.0319 (4)
C170.45154 (11)0.60894 (14)0.18663 (11)0.0385 (5)
C180.54944 (13)0.69342 (17)0.23643 (15)0.0600 (7)
H18A0.55020.73690.20060.072*
H18B0.58750.65050.22650.072*
C190.56359 (17)0.7339 (2)0.30383 (16)0.0811 (10)
H19A0.52640.77740.31240.122*
H19B0.61240.76000.30390.122*
H19C0.56110.69050.33890.122*
C200.31026 (12)0.54585 (14)0.09478 (10)0.0404 (5)
H20A0.28740.50010.06810.048*
H20B0.34630.57560.06610.048*
C210.28691 (12)0.67668 (12)0.15651 (10)0.0361 (5)
H21A0.32390.70610.12860.043*
H21B0.24910.71840.17000.043*
C220.19878 (11)0.63132 (14)0.06778 (10)0.0365 (5)
C230.15080 (13)0.56850 (16)0.04217 (11)0.0483 (6)
H230.15610.51110.05550.058*
C240.09497 (14)0.59180 (19)0.00343 (13)0.0583 (7)
H240.06210.55000.01990.070*
C250.08790 (13)0.67635 (19)0.02449 (12)0.0563 (7)
H250.05070.69090.05570.068*
C260.13505 (12)0.73984 (17)0.00012 (12)0.0483 (6)
C270.19051 (12)0.71622 (14)0.04632 (11)0.0406 (5)
H270.22270.75840.06330.049*
C280.12859 (16)0.8322 (2)0.02293 (17)0.0790 (9)
H28A0.17430.84960.04480.118*
H28B0.11950.86850.01600.118*
H28C0.08780.83760.05460.118*
N10.24122 (9)0.44287 (10)0.33290 (9)0.0364 (4)
N20.33984 (9)0.43436 (10)0.25214 (8)0.0325 (4)
N30.31940 (9)0.56596 (10)0.31470 (8)0.0320 (4)
N40.34792 (9)0.50907 (10)0.15396 (8)0.0343 (4)
N50.32233 (9)0.63989 (10)0.21670 (8)0.0306 (4)
N60.25262 (10)0.60692 (10)0.11782 (8)0.0364 (4)
O10.27578 (9)0.38472 (9)0.15775 (8)0.0469 (4)
O20.22632 (8)0.66624 (9)0.29289 (8)0.0422 (4)
O30.45827 (9)0.52344 (12)0.36771 (8)0.0553 (4)
O40.49553 (8)0.46721 (11)0.26752 (8)0.0544 (4)
O50.48131 (9)0.60350 (13)0.13262 (9)0.0622 (5)
O60.47578 (8)0.65276 (10)0.24036 (8)0.0481 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.079 (2)0.0484 (14)0.0691 (18)0.0121 (13)0.0201 (15)0.0033 (13)
C20.0509 (14)0.0436 (12)0.0441 (13)0.0091 (11)0.0080 (11)0.0035 (10)
C30.0470 (14)0.0571 (15)0.0664 (17)0.0101 (12)0.0222 (12)0.0003 (13)
C40.0407 (13)0.0597 (16)0.0733 (18)0.0061 (12)0.0193 (13)0.0025 (13)
C50.0411 (13)0.0434 (12)0.0550 (14)0.0039 (10)0.0081 (11)0.0017 (11)
C60.0352 (11)0.0377 (11)0.0350 (11)0.0029 (9)0.0031 (9)0.0022 (9)
C70.0400 (12)0.0414 (12)0.0405 (12)0.0012 (10)0.0054 (10)0.0034 (10)
C80.0405 (12)0.0324 (10)0.0405 (12)0.0018 (9)0.0068 (9)0.0019 (9)
C90.0391 (12)0.0369 (11)0.0355 (11)0.0003 (9)0.0057 (9)0.0014 (9)
C100.0323 (11)0.0315 (10)0.0409 (11)0.0071 (9)0.0044 (9)0.0050 (9)
C110.0277 (10)0.0282 (9)0.0384 (11)0.0023 (8)0.0018 (8)0.0061 (8)
C120.0309 (10)0.0316 (10)0.0342 (10)0.0021 (8)0.0019 (8)0.0002 (8)
C130.0335 (11)0.0417 (12)0.0406 (12)0.0010 (9)0.0009 (9)0.0101 (10)
C140.0326 (13)0.0772 (18)0.0723 (18)0.0126 (12)0.0030 (12)0.0087 (15)
C150.049 (3)0.071 (3)0.124 (8)0.005 (2)0.023 (5)0.025 (5)
C15'0.049 (3)0.071 (3)0.124 (8)0.005 (2)0.023 (5)0.025 (5)
C160.0287 (10)0.0337 (10)0.0333 (10)0.0029 (8)0.0017 (8)0.0002 (8)
C170.0297 (11)0.0422 (12)0.0435 (12)0.0025 (9)0.0025 (9)0.0089 (10)
C180.0301 (12)0.0647 (16)0.085 (2)0.0147 (11)0.0006 (12)0.0153 (15)
C190.0648 (19)0.083 (2)0.095 (2)0.0328 (17)0.0254 (17)0.0057 (18)
C200.0481 (13)0.0387 (11)0.0343 (11)0.0038 (10)0.0025 (10)0.0021 (9)
C210.0410 (12)0.0308 (10)0.0366 (11)0.0016 (9)0.0065 (9)0.0013 (9)
C220.0347 (11)0.0458 (12)0.0290 (10)0.0006 (9)0.0001 (9)0.0021 (9)
C230.0498 (14)0.0517 (13)0.0433 (13)0.0055 (11)0.0019 (11)0.0088 (11)
C240.0467 (14)0.0812 (19)0.0470 (14)0.0108 (13)0.0086 (11)0.0224 (14)
C250.0401 (13)0.089 (2)0.0400 (13)0.0070 (13)0.0089 (10)0.0029 (13)
C260.0364 (12)0.0676 (16)0.0410 (12)0.0061 (11)0.0006 (10)0.0076 (11)
C270.0340 (11)0.0479 (12)0.0398 (12)0.0005 (10)0.0027 (9)0.0037 (10)
C280.0587 (18)0.088 (2)0.091 (2)0.0069 (16)0.0165 (16)0.0415 (18)
N10.0352 (9)0.0334 (9)0.0407 (10)0.0001 (7)0.0089 (8)0.0012 (8)
N20.0324 (9)0.0301 (8)0.0349 (9)0.0022 (7)0.0049 (7)0.0001 (7)
N30.0303 (9)0.0325 (8)0.0332 (9)0.0010 (7)0.0027 (7)0.0006 (7)
N40.0381 (9)0.0319 (8)0.0330 (9)0.0031 (7)0.0011 (7)0.0012 (7)
N50.0295 (8)0.0296 (8)0.0328 (9)0.0012 (7)0.0029 (7)0.0016 (7)
N60.0422 (10)0.0325 (9)0.0344 (9)0.0030 (7)0.0079 (8)0.0035 (7)
O10.0533 (10)0.0368 (8)0.0507 (9)0.0042 (7)0.0017 (8)0.0092 (7)
O20.0359 (8)0.0403 (8)0.0505 (9)0.0094 (7)0.0026 (7)0.0070 (7)
O30.0412 (9)0.0844 (12)0.0402 (9)0.0005 (8)0.0064 (7)0.0054 (9)
O40.0344 (8)0.0740 (11)0.0546 (10)0.0209 (8)0.0046 (7)0.0056 (9)
O50.0478 (10)0.0900 (14)0.0487 (10)0.0068 (9)0.0168 (8)0.0049 (9)
O60.0317 (8)0.0581 (10)0.0544 (10)0.0146 (7)0.0027 (7)0.0002 (8)
Geometric parameters (Å, º) top
C1—C21.508 (3)C15—H15A0.9600
C1—H1A0.9600C15—H15B0.9600
C1—H1B0.9600C15—H15C0.9600
C1—H1C0.9600C15'—H15D0.9600
C2—C31.377 (3)C15'—H15E0.9600
C2—C71.395 (3)C15'—H15F0.9600
C3—C41.376 (3)C16—N41.448 (2)
C3—H30.9300C16—N51.456 (2)
C4—C51.374 (3)C16—C171.538 (3)
C4—H40.9300C17—O51.186 (3)
C5—C61.393 (3)C17—O61.323 (3)
C5—H50.9300C18—O61.460 (3)
C6—C71.391 (3)C18—C191.481 (4)
C6—N11.429 (2)C18—H18A0.9700
C7—H70.9300C18—H18B0.9700
C8—N21.456 (2)C19—H19A0.9600
C8—N11.462 (2)C19—H19B0.9600
C8—H8A0.9700C19—H19C0.9600
C8—H8B0.9700C20—N41.455 (3)
C9—N31.445 (2)C20—N61.468 (3)
C9—N11.470 (2)C20—H20A0.9700
C9—H9A0.9700C20—H20B0.9700
C9—H9B0.9700C21—N51.453 (2)
C10—O11.208 (2)C21—N61.453 (2)
C10—N21.378 (3)C21—H21A0.9700
C10—N41.391 (3)C21—H21B0.9700
C11—O21.211 (2)C22—C271.385 (3)
C11—N51.377 (2)C22—C231.388 (3)
C11—N31.384 (2)C22—N61.423 (3)
C12—N31.449 (2)C23—C241.386 (3)
C12—N21.455 (2)C23—H230.9300
C12—C131.543 (3)C24—C251.376 (4)
C12—C161.565 (3)C24—H240.9300
C13—O31.189 (3)C25—C261.378 (3)
C13—O41.327 (3)C25—H250.9300
C14—C15'1.466 (12)C26—C271.393 (3)
C14—O41.472 (3)C26—C281.500 (4)
C14—C151.481 (7)C27—H270.9300
C14—H14A0.9700C28—H28A0.9600
C14—H14B0.9700C28—H28B0.9600
C14—H14C0.9700C28—H28C0.9600
C14—H14D0.9700
C2—C1—H1A109.5N4—C16—N5112.10 (15)
C2—C1—H1B109.5N4—C16—C17113.20 (16)
H1A—C1—H1B109.5N5—C16—C17108.43 (15)
C2—C1—H1C109.5N4—C16—C12103.70 (15)
H1A—C1—H1C109.5N5—C16—C12102.95 (14)
H1B—C1—H1C109.5C17—C16—C12116.04 (16)
C3—C2—C7118.8 (2)O5—C17—O6126.7 (2)
C3—C2—C1120.7 (2)O5—C17—C16125.2 (2)
C7—C2—C1120.5 (2)O6—C17—C16108.05 (17)
C4—C3—C2120.8 (2)O6—C18—C19106.8 (2)
C4—C3—H3119.6O6—C18—H18A110.4
C2—C3—H3119.6C19—C18—H18A110.4
C5—C4—C3120.5 (2)O6—C18—H18B110.4
C5—C4—H4119.7C19—C18—H18B110.4
C3—C4—H4119.7H18A—C18—H18B108.6
C4—C5—C6120.1 (2)C18—C19—H19A109.5
C4—C5—H5119.9C18—C19—H19B109.5
C6—C5—H5119.9H19A—C19—H19B109.5
C7—C6—C5118.83 (19)C18—C19—H19C109.5
C7—C6—N1123.38 (18)H19A—C19—H19C109.5
C5—C6—N1117.78 (18)H19B—C19—H19C109.5
C6—C7—C2120.9 (2)N4—C20—N6109.33 (16)
C6—C7—H7119.5N4—C20—H20A109.8
C2—C7—H7119.5N6—C20—H20A109.8
N2—C8—N1108.58 (15)N4—C20—H20B109.8
N2—C8—H8A110.0N6—C20—H20B109.8
N1—C8—H8A110.0H20A—C20—H20B108.3
N2—C8—H8B110.0N5—C21—N6108.40 (15)
N1—C8—H8B110.0N5—C21—H21A110.0
H8A—C8—H8B108.4N6—C21—H21A110.0
N3—C9—N1109.90 (16)N5—C21—H21B110.0
N3—C9—H9A109.7N6—C21—H21B110.0
N1—C9—H9A109.7H21A—C21—H21B108.4
N3—C9—H9B109.7C27—C22—C23119.1 (2)
N1—C9—H9B109.7C27—C22—N6122.10 (19)
H9A—C9—H9B108.2C23—C22—N6118.69 (19)
O1—C10—N2125.82 (19)C24—C23—C22119.7 (2)
O1—C10—N4125.72 (19)C24—C23—H23120.2
N2—C10—N4108.38 (17)C22—C23—H23120.2
O2—C11—N5126.11 (18)C25—C24—C23120.4 (2)
O2—C11—N3125.87 (19)C25—C24—H24119.8
N5—C11—N3107.94 (16)C23—C24—H24119.8
N3—C12—N2111.61 (15)C24—C25—C26121.1 (2)
N3—C12—C13111.51 (16)C24—C25—H25119.5
N2—C12—C13110.57 (16)C26—C25—H25119.5
N3—C12—C16103.62 (14)C25—C26—C27118.3 (2)
N2—C12—C16103.42 (15)C25—C26—C28121.8 (2)
C13—C12—C16115.71 (16)C27—C26—C28119.9 (2)
O3—C13—O4126.3 (2)C22—C27—C26121.4 (2)
O3—C13—C12124.1 (2)C22—C27—H27119.3
O4—C13—C12109.68 (18)C26—C27—H27119.3
C15'—C14—O4108.7 (8)C26—C28—H28A109.5
O4—C14—C15111.7 (4)C26—C28—H28B109.5
C15'—C14—H14A132.4H28A—C28—H28B109.5
O4—C14—H14A109.3C26—C28—H28C109.5
C15—C14—H14A109.3H28A—C28—H28C109.5
C15'—C14—H14B85.1H28B—C28—H28C109.5
O4—C14—H14B109.3C6—N1—C8117.50 (16)
C15—C14—H14B109.3C6—N1—C9113.46 (15)
H14A—C14—H14B107.9C8—N1—C9109.62 (16)
C15'—C14—H14C110.1C10—N2—C12110.98 (15)
O4—C14—H14C109.7C10—N2—C8120.71 (17)
C15—C14—H14C129.4C12—N2—C8117.09 (15)
H14A—C14—H14C82.5C11—N3—C9118.69 (16)
C15'—C14—H14D109.7C11—N3—C12110.95 (15)
O4—C14—H14D110.2C9—N3—C12116.54 (15)
C15—C14—H14D83.1C10—N4—C16110.48 (15)
H14B—C14—H14D129.8C10—N4—C20118.04 (17)
H14C—C14—H14D108.3C16—N4—C20116.66 (15)
C14—C15—H15A109.5C11—N5—C21120.77 (16)
C14—C15—H15B109.5C11—N5—C16111.50 (15)
C14—C15—H15C109.5C21—N5—C16116.32 (15)
C14—C15'—H15D109.5C22—N6—C21116.54 (16)
C14—C15'—H15E109.5C22—N6—C20115.66 (16)
H15D—C15'—H15E109.5C21—N6—C20109.98 (16)
C14—C15'—H15F109.5C13—O4—C14116.89 (19)
H15D—C15'—H15F109.5C17—O6—C18118.24 (18)
H15E—C15'—H15F109.5
C7—C2—C3—C40.6 (4)N3—C12—N2—C842.0 (2)
C1—C2—C3—C4179.8 (3)C13—C12—N2—C882.7 (2)
C2—C3—C4—C50.1 (4)C16—C12—N2—C8152.79 (16)
C3—C4—C5—C60.4 (4)N1—C8—N2—C1088.0 (2)
C4—C5—C6—C70.2 (3)N1—C8—N2—C1252.4 (2)
C4—C5—C6—N1179.1 (2)O2—C11—N3—C926.0 (3)
C5—C6—C7—C20.4 (3)N5—C11—N3—C9157.13 (16)
N1—C6—C7—C2178.43 (19)O2—C11—N3—C12165.04 (18)
C3—C2—C7—C60.8 (3)N5—C11—N3—C1218.1 (2)
C1—C2—C7—C6180.0 (2)N1—C9—N3—C1185.2 (2)
N3—C12—C13—O36.8 (3)N1—C9—N3—C1251.6 (2)
N2—C12—C13—O3118.0 (2)N2—C12—N3—C1198.72 (18)
C16—C12—C13—O3124.9 (2)C13—C12—N3—C11137.07 (16)
N3—C12—C13—O4173.02 (16)C16—C12—N3—C1111.95 (19)
N2—C12—C13—O462.2 (2)N2—C12—N3—C941.3 (2)
C16—C12—C13—O454.9 (2)C13—C12—N3—C983.0 (2)
N3—C12—C16—N4118.72 (15)C16—C12—N3—C9151.93 (16)
N2—C12—C16—N42.15 (18)O1—C10—N4—C16164.86 (19)
C13—C12—C16—N4118.91 (18)N2—C10—N4—C1618.2 (2)
N3—C12—C16—N51.75 (18)O1—C10—N4—C2027.0 (3)
N2—C12—C16—N5114.82 (15)N2—C10—N4—C20156.09 (16)
C13—C12—C16—N5124.13 (17)N5—C16—N4—C1098.17 (18)
N3—C12—C16—C17116.50 (18)C17—C16—N4—C10138.78 (17)
N2—C12—C16—C17126.92 (17)C12—C16—N4—C1012.19 (19)
C13—C12—C16—C175.9 (2)N5—C16—N4—C2040.3 (2)
N4—C16—C17—O512.0 (3)C17—C16—N4—C2082.7 (2)
N5—C16—C17—O5113.0 (2)C12—C16—N4—C20150.68 (16)
C12—C16—C17—O5131.8 (2)N6—C20—N4—C1085.2 (2)
N4—C16—C17—O6170.98 (16)N6—C20—N4—C1650.1 (2)
N5—C16—C17—O664.0 (2)O2—C11—N5—C2124.1 (3)
C12—C16—C17—O651.2 (2)N3—C11—N5—C21159.02 (15)
C27—C22—C23—C241.0 (3)O2—C11—N5—C16166.26 (18)
N6—C22—C23—C24176.1 (2)N3—C11—N5—C1616.9 (2)
C22—C23—C24—C251.4 (4)N6—C21—N5—C1186.8 (2)
C23—C24—C25—C261.1 (4)N6—C21—N5—C1653.6 (2)
C24—C25—C26—C270.3 (4)N4—C16—N5—C11101.83 (18)
C24—C25—C26—C28179.5 (3)C17—C16—N5—C11132.47 (17)
C23—C22—C27—C260.2 (3)C12—C16—N5—C119.00 (19)
N6—C22—C27—C26176.70 (19)N4—C16—N5—C2142.1 (2)
C25—C26—C27—C220.1 (3)C17—C16—N5—C2183.6 (2)
C28—C26—C27—C22179.1 (2)C12—C16—N5—C21152.95 (16)
C7—C6—N1—C811.7 (3)C27—C22—N6—C2113.4 (3)
C5—C6—N1—C8167.11 (19)C23—C22—N6—C21163.54 (19)
C7—C6—N1—C9118.0 (2)C27—C22—N6—C20118.2 (2)
C5—C6—N1—C963.2 (2)C23—C22—N6—C2064.9 (2)
N2—C8—N1—C6168.14 (16)N5—C21—N6—C22163.66 (16)
N2—C8—N1—C960.4 (2)N5—C21—N6—C2062.2 (2)
N3—C9—N1—C6165.72 (16)N4—C20—N6—C22164.63 (17)
N3—C9—N1—C860.7 (2)N4—C20—N6—C2160.8 (2)
O1—C10—N2—C12166.38 (19)O3—C13—O4—C145.7 (3)
N4—C10—N2—C1216.7 (2)C12—C13—O4—C14174.17 (18)
O1—C10—N2—C823.7 (3)C15'—C14—O4—C13116.8 (10)
N4—C10—N2—C8159.39 (16)C15—C14—O4—C1387.0 (8)
N3—C12—N2—C10102.14 (18)O5—C17—O6—C185.5 (3)
C13—C12—N2—C10133.11 (17)C16—C17—O6—C18177.54 (18)
C16—C12—N2—C108.64 (19)C19—C18—O6—C17177.4 (2)

Experimental details

Crystal data
Chemical formulaC28H32N6O6
Mr548.60
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)292
a, b, c (Å)17.8591 (13), 15.4533 (11), 19.5649 (14)
V3)5399.6 (7)
Z8
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerBruker SMART 4K CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
30333, 5874, 4406
Rint0.050
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.057, 0.136, 1.05
No. of reflections5874
No. of parameters370
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.19

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

 

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