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The crystal structure of the title compound, C21H23N5O10, an important inter­mediate for mol­ecular tweezers, shows inter­molecular hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805028977/ww6404sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805028977/ww6404Isup2.hkl
Contains datablock I

CCDC reference: 273829

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.045
  • wR factor = 0.135
  • Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.77 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Derivatives of glycoluril have been employed in many applications, including polymer cross-linking, explosives, slow-release fertilizers, crosslinkers, assessment of drug reactivity (Jeon et al., 2005), stabilization of organic compounds against photo-degradation and combinatorial chemistry (Wu, Fettinger & Isaacs, 2002; Wu, Chakraborty et al., 2002). The use of glycoluril derivatives as building blocks for self-assembly, molecular recognition (Kang & Kim, 2005) and catalysis in chloroform has been reported (Conn & Rebek, 1997). Many methylene-bridged glycoluril dimers have been synthesized from soluble organic diethoxycarbonyl glycoluril derivatives (Witt et al., 2000). In this paper, we present the X-ray crystal structure of the title compound (I).

The X-ray crystallographic structure of (I) is shown in Fig. 1. Selected bond distances and torsion angles describing the molecular conformation are listed in Table 1. The molecules are connected by intermolecular hydrogen bonding (Fig 2). In the crystal structure, the angle between the two five-membered rings of the glycoluril is 110°.

Experimental top

The title compound was synthesized according to the literature procedure of Wu, Chakraborty et al. (2002), using paraformaldehyde (0.18 g, 6 mmol), 2,3-bisbromomethyl-1-methoxy-4-nitrobenzene (4 mmol, 1.36 g) and glycoluril (5.72 g, 20 mmol) as starting materials. Crystals suitable for data collection were obtained by slow evaporation from methanol–1,2-dichloroethane (Ratio?) solution at 293 K.

Refinement top

All H atoms were initially located in a difference Fourier map. Methyl H atoms were then constrained to an ideal geometry, with C—H distances of 0.96 Å and Uiso(H) = 1.5Ueq(C). All other H atoms were placed in geometrically idealized positions, with C—H distances in the range 0.93–0.97 Å, and were constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. A view of the molecule of (I), showing the atom-labelling scheme, with displacement ellipsoids drawn at the 50% probability level. H atoms are represented by circles of arbitrary size.
[Figure 2] Fig. 2. The intermolecular hydrogen bonding in the crystal structure of (I). Hydrogen-bonding interactions are indicated by dashed lines.
Diethyl 5,10-dihydro-9-methoxy-6-nitro-4,11-dioxo-cis-1H,3H,4H,11H-2-oxa- 3a,4a,10a,11a-tetraazabenz[f]indeno[2,1,7-ija]azulene-11b,11c-dicarboxylate top
Crystal data top
C21H23N5O10Z = 2
Mr = 505.44F(000) = 528
Triclinic, P1Dx = 1.499 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.756 (2) ÅCell parameters from 4159 reflections
b = 10.608 (2) Åθ = 2.6–28.3°
c = 11.716 (3) ŵ = 0.12 mm1
α = 110.123 (4)°T = 292 K
β = 98.754 (4)°Block, yellow
γ = 92.119 (4)°0.30 × 0.20 × 0.20 mm
V = 1119.9 (4) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
3412 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
Graphite monochromatorθmax = 26.0°, θmin = 1.9°
ϕ and ω scansh = 1212
8700 measured reflectionsk = 1313
4340 independent reflectionsl = 1414
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.073P)2 + 0.1853P]
where P = (Fo2 + 2Fc2)/3
4340 reflections(Δ/σ)max < 0.001
328 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C21H23N5O10γ = 92.119 (4)°
Mr = 505.44V = 1119.9 (4) Å3
Triclinic, P1Z = 2
a = 9.756 (2) ÅMo Kα radiation
b = 10.608 (2) ŵ = 0.12 mm1
c = 11.716 (3) ÅT = 292 K
α = 110.123 (4)°0.30 × 0.20 × 0.20 mm
β = 98.754 (4)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
3412 reflections with I > 2σ(I)
8700 measured reflectionsRint = 0.019
4340 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.135H-atom parameters constrained
S = 1.06Δρmax = 0.26 e Å3
4340 reflectionsΔρmin = 0.17 e Å3
328 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*/Ueq
C10.6843 (3)0.2774 (2)0.4461 (2)0.0717 (7)
H1A0.71160.27960.52760.108*
H1B0.70150.36070.38620.108*
H1C0.58690.26540.43260.108*
C20.7505 (2)0.0408 (2)0.50995 (19)0.0472 (5)
C30.6793 (2)0.0129 (2)0.6080 (2)0.0591 (6)
H30.63390.08290.62280.071*
C40.6757 (2)0.1178 (2)0.6835 (2)0.0594 (6)
H40.62490.13730.74750.071*
C50.7479 (2)0.2202 (2)0.66358 (17)0.0486 (5)
C60.81973 (19)0.19730 (19)0.56482 (16)0.0412 (4)
C70.81672 (18)0.06393 (18)0.48470 (17)0.0404 (4)
C80.87676 (19)0.03312 (19)0.36697 (17)0.0417 (4)
H8A0.97410.06840.38780.050*
H8B0.87220.06390.32610.050*
C90.8897 (2)0.30903 (19)0.53468 (16)0.0434 (4)
H9A0.89470.39350.60330.052*
H9B0.98410.28950.52340.052*
C100.67423 (18)0.03475 (17)0.21357 (16)0.0379 (4)
C110.6829 (2)0.36657 (17)0.42607 (16)0.0390 (4)
C120.82507 (18)0.23392 (17)0.30060 (15)0.0354 (4)
C130.96537 (19)0.26171 (19)0.26505 (18)0.0433 (4)
C141.0811 (3)0.2167 (3)0.0922 (3)0.0732 (7)
H14A1.15500.16700.11560.088*
H14B1.11520.31140.12200.088*
C151.0384 (4)0.1660 (3)0.0441 (3)0.0982 (10)
H15A0.99390.07580.07160.147*
H15B1.11910.16590.08180.147*
H15C0.97450.22340.06710.147*
C160.69285 (18)0.25597 (17)0.21718 (15)0.0358 (4)
C170.7186 (2)0.31826 (19)0.12066 (17)0.0435 (4)
C180.8069 (3)0.5209 (3)0.1019 (3)0.0697 (7)
H18A0.89040.58270.13920.084*
H18B0.81890.46270.02030.084*
C190.6869 (3)0.5974 (3)0.0909 (3)0.0929 (9)
H19A0.60310.53690.06120.139*
H19B0.69700.64260.03390.139*
H19C0.68180.66280.17030.139*
C200.46796 (19)0.1200 (2)0.12854 (18)0.0470 (5)
H20A0.44460.15350.06140.056*
H20B0.42660.02760.10110.056*
C210.4703 (2)0.3364 (2)0.27194 (19)0.0483 (5)
H21A0.43070.39070.34190.058*
H21B0.44690.37130.20570.058*
N10.7426 (2)0.3560 (2)0.75081 (16)0.0600 (5)
N20.80236 (15)0.09153 (14)0.28193 (13)0.0360 (3)
N30.81338 (16)0.32315 (14)0.42234 (13)0.0387 (4)
N40.61829 (15)0.12341 (14)0.15920 (13)0.0379 (3)
N50.61892 (16)0.34618 (14)0.30650 (13)0.0384 (4)
O10.76296 (16)0.16808 (14)0.43397 (14)0.0594 (4)
O20.8501 (2)0.42990 (19)0.79215 (16)0.0834 (6)
O30.6308 (2)0.38728 (18)0.78133 (16)0.0791 (5)
O40.62129 (14)0.07552 (13)0.19868 (14)0.0545 (4)
O50.63453 (16)0.41730 (14)0.51834 (12)0.0541 (4)
O61.06315 (16)0.32901 (19)0.33582 (15)0.0732 (5)
O70.95947 (14)0.19839 (14)0.14557 (13)0.0517 (4)
O80.67792 (18)0.26598 (17)0.01277 (13)0.0667 (4)
O90.78743 (16)0.43882 (14)0.17747 (13)0.0563 (4)
O100.41237 (13)0.20003 (14)0.23236 (13)0.0502 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0908 (18)0.0483 (13)0.0754 (17)0.0123 (12)0.0087 (14)0.0254 (12)
C20.0523 (11)0.0441 (11)0.0488 (11)0.0047 (9)0.0033 (9)0.0235 (9)
C30.0711 (14)0.0567 (13)0.0599 (13)0.0001 (11)0.0184 (11)0.0313 (11)
C40.0727 (15)0.0660 (15)0.0487 (12)0.0068 (11)0.0204 (11)0.0280 (11)
C50.0590 (12)0.0511 (12)0.0350 (10)0.0070 (9)0.0036 (9)0.0163 (9)
C60.0429 (10)0.0464 (11)0.0344 (10)0.0037 (8)0.0020 (7)0.0181 (8)
C70.0411 (10)0.0432 (10)0.0399 (10)0.0071 (8)0.0025 (8)0.0198 (8)
C80.0423 (10)0.0404 (10)0.0455 (11)0.0105 (8)0.0069 (8)0.0189 (8)
C90.0503 (11)0.0412 (10)0.0345 (10)0.0008 (8)0.0008 (8)0.0123 (8)
C100.0429 (10)0.0326 (9)0.0358 (9)0.0053 (7)0.0109 (7)0.0072 (7)
C110.0548 (11)0.0279 (9)0.0343 (10)0.0074 (7)0.0090 (8)0.0102 (7)
C120.0420 (10)0.0314 (9)0.0319 (9)0.0026 (7)0.0059 (7)0.0105 (7)
C130.0432 (10)0.0429 (10)0.0452 (11)0.0006 (8)0.0053 (8)0.0190 (9)
C140.0599 (14)0.0839 (17)0.0849 (18)0.0027 (12)0.0400 (13)0.0303 (15)
C150.125 (3)0.094 (2)0.083 (2)0.0007 (18)0.0662 (19)0.0215 (17)
C160.0433 (10)0.0332 (9)0.0308 (9)0.0066 (7)0.0085 (7)0.0102 (7)
C170.0487 (11)0.0472 (11)0.0375 (11)0.0085 (8)0.0090 (8)0.0178 (9)
C180.0809 (16)0.0751 (16)0.0756 (16)0.0021 (13)0.0198 (13)0.0528 (14)
C190.124 (3)0.0777 (19)0.102 (2)0.0239 (17)0.0306 (19)0.0571 (18)
C200.0418 (10)0.0498 (11)0.0437 (11)0.0072 (8)0.0019 (8)0.0114 (9)
C210.0529 (12)0.0498 (12)0.0437 (11)0.0195 (9)0.0119 (9)0.0157 (9)
N10.0848 (14)0.0602 (12)0.0363 (9)0.0071 (11)0.0101 (9)0.0188 (9)
N20.0403 (8)0.0317 (8)0.0370 (8)0.0051 (6)0.0069 (6)0.0132 (6)
N30.0477 (9)0.0353 (8)0.0312 (8)0.0038 (6)0.0032 (6)0.0112 (6)
N40.0395 (8)0.0334 (8)0.0361 (8)0.0050 (6)0.0033 (6)0.0077 (6)
N50.0487 (9)0.0360 (8)0.0314 (8)0.0128 (6)0.0093 (6)0.0113 (6)
O10.0788 (10)0.0413 (8)0.0631 (10)0.0035 (7)0.0155 (8)0.0238 (7)
O20.1094 (15)0.0730 (12)0.0498 (10)0.0157 (11)0.0104 (10)0.0029 (9)
O30.1034 (14)0.0799 (12)0.0611 (11)0.0329 (10)0.0337 (10)0.0235 (9)
O40.0571 (8)0.0344 (7)0.0666 (10)0.0032 (6)0.0017 (7)0.0155 (7)
O50.0748 (10)0.0528 (8)0.0346 (7)0.0235 (7)0.0160 (7)0.0111 (6)
O60.0548 (9)0.0950 (13)0.0601 (10)0.0241 (9)0.0021 (8)0.0217 (9)
O70.0455 (7)0.0591 (9)0.0496 (8)0.0008 (6)0.0198 (6)0.0138 (7)
O80.0872 (11)0.0786 (11)0.0331 (8)0.0012 (9)0.0054 (7)0.0215 (8)
O90.0775 (10)0.0489 (8)0.0498 (9)0.0012 (7)0.0123 (7)0.0270 (7)
O100.0431 (7)0.0566 (9)0.0509 (8)0.0106 (6)0.0120 (6)0.0170 (7)
Geometric parameters (Å, º) top
C1—O11.426 (3)C13—O61.187 (2)
C1—H1A0.9600C13—O71.319 (2)
C1—H1B0.9600C14—O71.459 (2)
C1—H1C0.9600C14—C151.484 (4)
C2—O11.359 (2)C14—H14A0.9700
C2—C31.383 (3)C14—H14B0.9700
C2—C71.404 (3)C15—H15A0.9600
C3—C41.369 (3)C15—H15B0.9600
C3—H30.9300C15—H15C0.9600
C4—C51.377 (3)C16—N41.444 (2)
C4—H40.9300C16—N51.457 (2)
C5—C61.398 (3)C16—C171.538 (2)
C5—N11.460 (3)C17—O81.188 (2)
C6—C71.399 (3)C17—O91.321 (2)
C6—C91.515 (3)C18—C191.463 (4)
C7—C81.517 (3)C18—O91.465 (2)
C8—N21.463 (2)C18—H18A0.9700
C8—H8A0.9700C18—H18B0.9700
C8—H8B0.9700C19—H19A0.9600
C9—N31.468 (2)C19—H19B0.9600
C9—H9A0.9700C19—H19C0.9600
C9—H9B0.9700C20—O101.421 (2)
C10—O41.205 (2)C20—N41.452 (2)
C10—N21.369 (2)C20—H20A0.9700
C10—N41.390 (2)C20—H20B0.9700
C11—O51.206 (2)C21—O101.423 (2)
C11—N31.372 (2)C21—N51.435 (2)
C11—N51.384 (2)C21—H21A0.9700
C12—N31.439 (2)C21—H21B0.9700
C12—N21.453 (2)N1—O21.213 (3)
C12—C131.537 (2)N1—O31.221 (3)
C12—C161.571 (2)
O1—C1—H1A109.5C14—C15—H15B109.5
O1—C1—H1B109.5H15A—C15—H15B109.5
H1A—C1—H1B109.5C14—C15—H15C109.5
O1—C1—H1C109.5H15A—C15—H15C109.5
H1A—C1—H1C109.5H15B—C15—H15C109.5
H1B—C1—H1C109.5N4—C16—N5111.54 (14)
O1—C2—C3123.38 (18)N4—C16—C17111.24 (14)
O1—C2—C7115.93 (18)N5—C16—C17109.63 (14)
C3—C2—C7120.68 (19)N4—C16—C12104.10 (13)
C4—C3—C2120.0 (2)N5—C16—C12103.10 (13)
C4—C3—H3120.0C17—C16—C12116.90 (14)
C2—C3—H3120.0O8—C17—O9126.44 (18)
C3—C4—C5119.4 (2)O8—C17—C16124.30 (18)
C3—C4—H4120.3O9—C17—C16109.22 (15)
C5—C4—H4120.3C19—C18—O9110.8 (2)
C4—C5—C6122.67 (19)C19—C18—H18A109.5
C4—C5—N1115.84 (19)O9—C18—H18A109.5
C6—C5—N1121.47 (18)C19—C18—H18B109.5
C5—C6—C7117.35 (17)O9—C18—H18B109.5
C5—C6—C9123.66 (17)H18A—C18—H18B108.1
C7—C6—C9118.80 (16)C18—C19—H19A109.5
C6—C7—C2119.67 (17)C18—C19—H19B109.5
C6—C7—C8120.29 (16)H19A—C19—H19B109.5
C2—C7—C8119.94 (17)C18—C19—H19C109.5
N2—C8—C7112.31 (14)H19A—C19—H19C109.5
N2—C8—H8A109.1H19B—C19—H19C109.5
C7—C8—H8A109.1O10—C20—N4110.87 (15)
N2—C8—H8B109.1O10—C20—H20A109.5
C7—C8—H8B109.1N4—C20—H20A109.5
H8A—C8—H8B107.9O10—C20—H20B109.5
N3—C9—C6111.48 (14)N4—C20—H20B109.5
N3—C9—H9A109.3H20A—C20—H20B108.1
C6—C9—H9A109.3O10—C21—N5110.72 (14)
N3—C9—H9B109.3O10—C21—H21A109.5
C6—C9—H9B109.3N5—C21—H21A109.5
H9A—C9—H9B108.0O10—C21—H21B109.5
O4—C10—N2125.98 (17)N5—C21—H21B109.5
O4—C10—N4125.68 (17)H21A—C21—H21B108.1
N2—C10—N4108.27 (14)O2—N1—O3123.6 (2)
O5—C11—N3125.57 (17)O2—N1—C5118.3 (2)
O5—C11—N5126.22 (17)O3—N1—C5118.0 (2)
N3—C11—N5108.18 (15)C10—N2—C12112.36 (14)
N3—C12—N2114.23 (14)C10—N2—C8120.97 (14)
N3—C12—C13112.07 (14)C12—N2—C8121.83 (14)
N2—C12—C13109.38 (14)C11—N3—C12111.60 (14)
N3—C12—C16103.11 (13)C11—N3—C9117.68 (15)
N2—C12—C16102.39 (13)C12—N3—C9122.33 (15)
C13—C12—C16115.31 (14)C10—N4—C16110.76 (14)
O6—C13—O7126.17 (18)C10—N4—C20119.12 (15)
O6—C13—C12124.39 (18)C16—N4—C20115.74 (14)
O7—C13—C12109.44 (15)C11—N5—C21122.03 (15)
O7—C14—C15107.9 (2)C11—N5—C16110.98 (14)
O7—C14—H14A110.1C21—N5—C16116.37 (14)
C15—C14—H14A110.1C2—O1—C1118.21 (18)
O7—C14—H14B110.1C13—O7—C14118.00 (17)
C15—C14—H14B110.1C17—O9—C18117.11 (17)
H14A—C14—H14B108.4C20—O10—C21109.93 (14)
C14—C15—H15A109.5
O1—C2—C3—C4177.5 (2)C16—C12—N2—C106.52 (18)
C7—C2—C3—C41.5 (3)N3—C12—N2—C851.4 (2)
C2—C3—C4—C52.6 (4)C13—C12—N2—C875.16 (19)
C3—C4—C5—C63.5 (3)C16—C12—N2—C8162.06 (14)
C3—C4—C5—N1177.9 (2)C7—C8—N2—C1075.8 (2)
C4—C5—C6—C70.2 (3)C7—C8—N2—C1277.7 (2)
N1—C5—C6—C7178.78 (18)O5—C11—N3—C12163.25 (17)
C4—C5—C6—C9174.65 (19)N5—C11—N3—C1218.73 (19)
N1—C5—C6—C93.9 (3)O5—C11—N3—C914.2 (3)
C5—C6—C7—C23.8 (3)N5—C11—N3—C9167.75 (14)
C9—C6—C7—C2178.99 (17)N2—C12—N3—C1195.88 (17)
C5—C6—C7—C8172.41 (17)C13—C12—N3—C11139.01 (15)
C9—C6—C7—C82.8 (3)C16—C12—N3—C1114.39 (17)
O1—C2—C7—C6174.30 (16)N2—C12—N3—C951.5 (2)
C3—C2—C7—C64.8 (3)C13—C12—N3—C973.64 (19)
O1—C2—C7—C89.4 (3)C16—C12—N3—C9161.74 (14)
C3—C2—C7—C8171.46 (18)C6—C9—N3—C1166.5 (2)
C6—C7—C8—N263.0 (2)C6—C9—N3—C1279.0 (2)
C2—C7—C8—N2113.21 (19)O4—C10—N4—C16167.50 (17)
C5—C6—C9—N3108.2 (2)N2—C10—N4—C1615.36 (18)
C7—C6—C9—N366.6 (2)O4—C10—N4—C2029.5 (3)
N3—C12—C13—O613.8 (3)N2—C10—N4—C20153.33 (15)
N2—C12—C13—O6113.9 (2)N5—C16—N4—C1099.68 (16)
C16—C12—C13—O6131.4 (2)C17—C16—N4—C10137.58 (15)
N3—C12—C13—O7166.84 (15)C12—C16—N4—C1010.84 (17)
N2—C12—C13—O765.42 (18)N5—C16—N4—C2039.8 (2)
C16—C12—C13—O749.3 (2)C17—C16—N4—C2082.92 (18)
N3—C12—C16—N4121.48 (13)C12—C16—N4—C20150.34 (14)
N2—C12—C16—N42.63 (16)O10—C20—N4—C1084.80 (19)
C13—C12—C16—N4116.05 (15)O10—C20—N4—C1651.2 (2)
N3—C12—C16—N54.92 (16)O5—C11—N5—C2123.8 (3)
N2—C12—C16—N5113.93 (14)N3—C11—N5—C21158.19 (15)
C13—C12—C16—N5127.39 (15)O5—C11—N5—C16167.04 (17)
N3—C12—C16—C17115.40 (16)N3—C11—N5—C1614.96 (19)
N2—C12—C16—C17125.75 (15)O10—C21—N5—C1190.42 (19)
C13—C12—C16—C177.1 (2)O10—C21—N5—C1651.0 (2)
N4—C16—C17—O82.5 (3)N4—C16—N5—C11105.40 (16)
N5—C16—C17—O8121.3 (2)C17—C16—N5—C11130.93 (15)
C12—C16—C17—O8121.9 (2)C12—C16—N5—C115.74 (17)
N4—C16—C17—O9179.71 (15)N4—C16—N5—C2140.1 (2)
N5—C16—C17—O956.45 (19)C17—C16—N5—C2183.56 (18)
C12—C16—C17—O960.3 (2)C12—C16—N5—C21151.25 (15)
C4—C5—N1—O2135.0 (2)C3—C2—O1—C18.2 (3)
C6—C5—N1—O246.4 (3)C7—C2—O1—C1172.69 (19)
C4—C5—N1—O342.5 (3)O6—C13—O7—C143.2 (3)
C6—C5—N1—O3136.1 (2)C12—C13—O7—C14177.43 (18)
O4—C10—N2—C12169.24 (17)C15—C14—O7—C13166.0 (2)
N4—C10—N2—C1213.63 (19)O8—C17—O9—C184.9 (3)
O4—C10—N2—C813.5 (3)C16—C17—O9—C18172.78 (17)
N4—C10—N2—C8169.41 (14)C19—C18—O9—C1786.1 (3)
N3—C12—N2—C10104.18 (17)N4—C20—O10—C2160.3 (2)
C13—C12—N2—C10129.30 (15)N5—C21—O10—C2060.17 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O10i0.932.503.342 (3)150
C21—H21A···O5ii0.972.313.233 (2)158
C18—H18A···O2iii0.972.563.343 (3)138
C14—H14B···O2iii0.972.573.519 (3)167
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y+1, z+1; (iii) x+2, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC21H23N5O10
Mr505.44
Crystal system, space groupTriclinic, P1
Temperature (K)292
a, b, c (Å)9.756 (2), 10.608 (2), 11.716 (3)
α, β, γ (°)110.123 (4), 98.754 (4), 92.119 (4)
V3)1119.9 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
8700, 4340, 3412
Rint0.019
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.135, 1.06
No. of reflections4340
No. of parameters328
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.17

Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Selected geometric parameters (Å, º) top
C2—C31.383 (3)C10—N41.390 (2)
C2—C71.404 (3)C12—N21.453 (2)
C7—C81.517 (3)C12—C161.571 (2)
C8—N21.463 (2)C16—N41.444 (2)
C10—O41.205 (2)C20—N41.452 (2)
C10—N21.369 (2)C21—O101.423 (2)
C2—C7—C8119.94 (17)N2—C12—C16102.39 (13)
N2—C8—C7112.31 (14)O10—C20—N4110.87 (15)
N2—C10—N4108.27 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O10i0.932.503.342 (3)150
C21—H21A···O5ii0.972.313.233 (2)158
C18—H18A···O2iii0.972.563.343 (3)138
C14—H14B···O2iii0.972.573.519 (3)167
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y+1, z+1; (iii) x+2, y+1, z+1.
 

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