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In the title compound, C20H21N5O9, the dihedral angle between the two five-membered rings of the glycoluril system is 68.79 (14)° and the crystal structure is stabilized by inter­molecular C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027741/jh6016sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027741/jh6016Isup2.hkl
Contains datablock I

CCDC reference: 281774

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.065
  • wR factor = 0.172
  • Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.99 Ratio PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 3.15 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.43 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - N1 .. 6.99 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The design and synthesis of host molecules for binding of neutral guest molecules continues to be an area of interest in supramolecular chemistry. In recent years, many molecular clips based on glycoluril and its derivatives have been studied, which can bind dihydroxy-substituted aromatic guests by means of hydrogen bonds as well as π-π interactions (Sijbesma & Notle, 1991; Reek et al., 1997; Rowan et al., 1999). In this paper, we report the crystal structure of the title compound (I) (Fig. 1), a new half molecular clip based on diethoxycarbonyl glycoluril. Selected bond lengths and angles are listed in Table 1. The crystal packing is mainly connected by intermolecular C—H···O interactions (Table 2 and Fig. 2).

Experimental top

1,2-Bis(chloromethyl)-4-nitrobenzene (1.1 g, 5 mmol), diethoxycarbonyl glycoluril (1.43 g, 5 mmol), formaldehyde (2.4 g, 40 mmol) and trifluoroacetic acid (30 ml) were used as starting materials to synthesize the title compound according to the literature (Wu et al., 2002). Crystals suitable for X-ray diffraction were grown by slow evaporation of the MeCN–MeOH(1:1) solutions for title compound at ambient conditions.

Refinement top

After their location on a different Fourier map, H atoms were placed in calculated positions and allowed to ride on their parent atoms, with C—H = 0.93–0.97 Å, and Uiso = 1.2 − 1.5 Ueq(C).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. View of the molecule of (I), showing the atom-labelling scheme.
[Figure 2] Fig. 2. C—H···O intermolecular hydrogen-bonding (dashed lines).
Diethyl (11bR,11cS)-rel-5,10-dihydro-7-nitro-4,11-dioxo-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
C20H21N5O9F(000) = 992
Mr = 475.42Dx = 1.467 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2ybcCell parameters from 3635 reflections
a = 10.0454 (18) Åθ = 2.2–25.1°
b = 25.564 (5) ŵ = 0.12 mm1
c = 8.4997 (15) ÅT = 292 K
β = 99.427 (3)°Block, colorless
V = 2153.2 (7) Å30.30 × 0.20 × 0.10 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
4225 independent reflections
Radiation source: fine-focus sealed tube3284 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.053
ϕ and ω scansθmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
h = 1211
Tmin = 0.966, Tmax = 0.988k = 3131
11538 measured reflectionsl = 106
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0729P)2 + 1.0059P]
where P = (Fo2 + 2Fc2)/3
4225 reflections(Δ/σ)max = 0.001
309 parametersΔρmax = 0.48 e Å3
0 restraintsΔρmin = 0.32 e Å3
Crystal data top
C20H21N5O9V = 2153.2 (7) Å3
Mr = 475.42Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.0454 (18) ŵ = 0.12 mm1
b = 25.564 (5) ÅT = 292 K
c = 8.4997 (15) Å0.30 × 0.20 × 0.10 mm
β = 99.427 (3)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
4225 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
3284 reflections with I > 2σ(I)
Tmin = 0.966, Tmax = 0.988Rint = 0.053
11538 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0650 restraints
wR(F2) = 0.172H-atom parameters constrained
S = 1.05Δρmax = 0.48 e Å3
4225 reflectionsΔρmin = 0.32 e Å3
309 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
C10.1389 (3)0.42010 (13)0.6095 (4)0.0617 (8)
C20.0849 (3)0.45554 (12)0.7083 (3)0.0556 (7)
H20.02870.44400.77790.067*
C30.2213 (3)0.43524 (15)0.5052 (4)0.0673 (9)
H30.25600.41090.44150.081*
C40.2513 (3)0.48671 (15)0.4970 (3)0.0627 (8)
H40.30650.49760.42540.075*
C50.2016 (3)0.52406 (12)0.5933 (3)0.0505 (7)
C60.1168 (2)0.50771 (11)0.7001 (3)0.0465 (6)
C70.0658 (2)0.54637 (11)0.8104 (3)0.0444 (6)
H7A0.01360.57330.74750.053*
H7B0.00650.52850.87220.053*
C80.2401 (3)0.58054 (13)0.5820 (3)0.0547 (7)
H8A0.29460.58420.49830.066*
H8B0.15880.60110.55160.066*
C90.2468 (2)0.54454 (10)1.0469 (3)0.0405 (6)
C100.4515 (2)0.59340 (10)0.7716 (3)0.0455 (6)
C110.2515 (2)0.61362 (10)0.8665 (3)0.0411 (6)
C120.1604 (2)0.66209 (11)0.8355 (3)0.0484 (6)
C130.0130 (3)0.71658 (13)0.9564 (5)0.0777 (10)
H13A0.02040.73281.06060.093*
H13B0.03630.74250.88220.093*
C140.1244 (4)0.6991 (2)0.9051 (8)0.1211 (19)
H14A0.13860.69250.79240.182*
H14B0.18590.72570.92810.182*
H14C0.13980.66760.96070.182*
C150.3742 (2)0.61854 (10)1.0053 (3)0.0412 (6)
C160.3883 (3)0.66993 (11)1.0983 (4)0.0517 (7)
C170.4105 (4)0.76209 (12)1.0753 (5)0.0721 (9)
H17A0.36350.78771.00220.087*
H17B0.37100.76261.17210.087*
C180.5533 (5)0.77571 (18)1.1127 (7)0.1125 (16)
H18A0.59750.75271.19420.169*
H18B0.56220.81121.15010.169*
H18C0.59390.77221.01870.169*
C190.4785 (3)0.55311 (12)1.2008 (3)0.0535 (7)
H19A0.51460.57731.28490.064*
H19B0.45640.52081.25030.064*
C200.6092 (2)0.58940 (11)1.0257 (4)0.0517 (7)
H20A0.67730.58160.96030.062*
H20B0.64630.61511.10490.062*
N10.1078 (4)0.36465 (13)0.6249 (5)0.0868 (9)
N20.17610 (19)0.57088 (8)0.9189 (2)0.0394 (5)
N30.3152 (2)0.60163 (9)0.7303 (2)0.0456 (5)
N40.35689 (19)0.57505 (9)1.1083 (3)0.0453 (5)
N50.49109 (19)0.61109 (8)0.9262 (3)0.0431 (5)
O10.0227 (5)0.35157 (13)0.6997 (5)0.1286 (13)
O20.1678 (5)0.33316 (15)0.5526 (7)0.168 (2)
O30.21406 (17)0.50392 (8)1.1014 (2)0.0533 (5)
O40.52464 (19)0.57600 (8)0.6843 (2)0.0578 (5)
O50.1399 (2)0.68482 (9)0.7114 (3)0.0756 (7)
O60.1065 (2)0.67258 (8)0.9643 (3)0.0603 (5)
O70.3960 (3)0.67188 (10)1.2402 (3)0.0871 (8)
O80.3943 (2)0.70982 (7)1.0026 (2)0.0593 (5)
O90.57720 (17)0.54315 (8)1.1034 (2)0.0537 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0488 (15)0.0693 (19)0.0590 (18)0.0059 (14)0.0147 (14)0.0124 (15)
C20.0411 (14)0.0709 (19)0.0500 (16)0.0025 (13)0.0070 (12)0.0041 (14)
C30.0532 (17)0.091 (3)0.0537 (19)0.0037 (16)0.0025 (15)0.0219 (17)
C40.0463 (15)0.100 (3)0.0405 (15)0.0054 (16)0.0028 (12)0.0083 (15)
C50.0358 (12)0.0801 (19)0.0332 (13)0.0054 (12)0.0012 (10)0.0027 (13)
C60.0323 (12)0.0625 (16)0.0411 (14)0.0031 (11)0.0043 (10)0.0002 (12)
C70.0298 (11)0.0593 (15)0.0437 (14)0.0008 (10)0.0052 (10)0.0048 (12)
C80.0424 (14)0.086 (2)0.0362 (14)0.0067 (13)0.0079 (11)0.0110 (13)
C90.0299 (11)0.0519 (14)0.0411 (13)0.0016 (10)0.0099 (10)0.0076 (11)
C100.0372 (12)0.0510 (14)0.0503 (15)0.0018 (11)0.0131 (11)0.0135 (12)
C110.0338 (12)0.0500 (14)0.0400 (13)0.0023 (10)0.0070 (10)0.0081 (11)
C120.0356 (12)0.0526 (15)0.0566 (16)0.0032 (11)0.0064 (12)0.0154 (13)
C130.069 (2)0.0600 (19)0.107 (3)0.0233 (16)0.021 (2)0.0001 (19)
C140.061 (2)0.116 (4)0.181 (5)0.031 (2)0.003 (3)0.021 (4)
C150.0317 (11)0.0492 (14)0.0429 (13)0.0023 (10)0.0069 (10)0.0078 (11)
C160.0446 (14)0.0582 (17)0.0512 (16)0.0041 (12)0.0049 (12)0.0001 (13)
C170.084 (2)0.0534 (17)0.082 (2)0.0051 (16)0.0249 (19)0.0084 (17)
C180.097 (3)0.082 (3)0.157 (5)0.025 (2)0.015 (3)0.041 (3)
C190.0384 (13)0.0655 (17)0.0533 (16)0.0003 (12)0.0021 (12)0.0179 (14)
C200.0305 (12)0.0589 (16)0.0638 (17)0.0037 (11)0.0020 (12)0.0048 (14)
N10.109 (2)0.079 (2)0.097 (2)0.0055 (18)0.0018 (18)0.0196 (19)
N20.0319 (9)0.0472 (11)0.0390 (11)0.0008 (8)0.0055 (8)0.0055 (9)
N30.0345 (10)0.0648 (14)0.0387 (11)0.0031 (9)0.0092 (9)0.0110 (10)
N40.0326 (10)0.0574 (13)0.0446 (12)0.0020 (9)0.0027 (9)0.0144 (10)
N50.0315 (10)0.0488 (12)0.0494 (12)0.0008 (8)0.0075 (9)0.0048 (10)
O10.172 (4)0.086 (2)0.141 (3)0.020 (2)0.066 (3)0.000 (2)
O20.185 (4)0.087 (2)0.256 (5)0.012 (2)0.104 (4)0.062 (3)
O30.0387 (9)0.0638 (12)0.0582 (12)0.0047 (8)0.0106 (8)0.0200 (10)
O40.0468 (10)0.0728 (13)0.0583 (12)0.0080 (9)0.0218 (9)0.0104 (10)
O50.0767 (15)0.0760 (15)0.0739 (15)0.0234 (12)0.0121 (12)0.0326 (12)
O60.0545 (11)0.0607 (12)0.0684 (13)0.0185 (9)0.0177 (10)0.0062 (10)
O70.133 (2)0.0752 (16)0.0516 (14)0.0078 (15)0.0110 (14)0.0063 (11)
O80.0702 (13)0.0468 (11)0.0612 (12)0.0047 (9)0.0116 (10)0.0004 (9)
O90.0334 (9)0.0605 (11)0.0653 (12)0.0036 (8)0.0025 (8)0.0145 (10)
Geometric parameters (Å, º) top
C1—C31.364 (5)C13—C141.448 (6)
C1—C21.403 (4)C13—O61.460 (3)
C1—N11.462 (5)C13—H13A0.9700
C2—C61.376 (4)C13—H13B0.9700
C2—H20.9300C14—H14A0.9600
C3—C41.354 (5)C14—H14B0.9600
C3—H30.9300C14—H14C0.9600
C4—C51.402 (4)C15—N41.443 (3)
C4—H40.9300C15—N51.458 (3)
C5—C61.406 (4)C15—C161.527 (4)
C5—C81.502 (4)C16—O71.197 (4)
C6—C71.509 (4)C16—O81.312 (3)
C7—N21.461 (3)C17—C181.460 (6)
C7—H7A0.9700C17—O81.470 (4)
C7—H7B0.9700C17—H17A0.9700
C8—N31.462 (4)C17—H17B0.9700
C8—H8A0.9700C18—H18A0.9600
C8—H8B0.9700C18—H18B0.9600
C9—O31.205 (3)C18—H18C0.9600
C9—N21.374 (3)C19—O91.415 (3)
C9—N41.384 (3)C19—N41.452 (3)
C10—O41.211 (3)C19—H19A0.9700
C10—N31.372 (3)C19—H19B0.9700
C10—N51.385 (3)C20—O91.417 (3)
C11—N21.441 (3)C20—N51.450 (3)
C11—N31.444 (3)C20—H20A0.9700
C11—C121.538 (4)C20—H20B0.9700
C11—C151.566 (3)N1—O11.193 (4)
C12—O51.192 (3)N1—O21.229 (5)
C12—O61.326 (3)
C3—C1—C2122.7 (3)C13—C14—H14C109.5
C3—C1—N1119.7 (3)H14A—C14—H14C109.5
C2—C1—N1117.6 (3)H14B—C14—H14C109.5
C6—C2—C1118.7 (3)N4—C15—N5111.5 (2)
C6—C2—H2120.7N4—C15—C16111.0 (2)
C1—C2—H2120.7N5—C15—C16109.7 (2)
C4—C3—C1118.2 (3)N4—C15—C11103.70 (19)
C4—C3—H3120.9N5—C15—C11103.62 (19)
C1—C3—H3120.9C16—C15—C11117.0 (2)
C3—C4—C5121.9 (3)O7—C16—O8126.2 (3)
C3—C4—H4119.1O7—C16—C15122.8 (3)
C5—C4—H4119.1O8—C16—C15111.0 (2)
C4—C5—C6119.1 (3)C18—C17—O8110.2 (3)
C4—C5—C8119.8 (3)C18—C17—H17A109.6
C6—C5—C8121.1 (3)O8—C17—H17A109.6
C2—C6—C5119.4 (3)C18—C17—H17B109.6
C2—C6—C7119.9 (3)O8—C17—H17B109.6
C5—C6—C7120.6 (3)H17A—C17—H17B108.1
N2—C7—C6111.93 (19)C17—C18—H18A109.5
N2—C7—H7A109.2C17—C18—H18B109.5
C6—C7—H7A109.2H18A—C18—H18B109.5
N2—C7—H7B109.2C17—C18—H18C109.5
C6—C7—H7B109.2H18A—C18—H18C109.5
H7A—C7—H7B107.9H18B—C18—H18C109.5
N3—C8—C5113.6 (2)O9—C19—N4111.2 (2)
N3—C8—H8A108.8O9—C19—H19A109.4
C5—C8—H8A108.8N4—C19—H19A109.4
N3—C8—H8B108.8O9—C19—H19B109.4
C5—C8—H8B108.8N4—C19—H19B109.4
H8A—C8—H8B107.7H19A—C19—H19B108.0
O3—C9—N2126.0 (2)O9—C20—N5111.40 (19)
O3—C9—N4126.3 (2)O9—C20—H20A109.3
N2—C9—N4107.5 (2)N5—C20—H20A109.3
O4—C10—N3125.4 (3)O9—C20—H20B109.3
O4—C10—N5126.3 (2)N5—C20—H20B109.3
N3—C10—N5108.2 (2)H20A—C20—H20B108.0
N2—C11—N3114.3 (2)O1—N1—O2122.4 (4)
N2—C11—C12109.61 (19)O1—N1—C1120.1 (4)
N3—C11—C12111.3 (2)O2—N1—C1117.4 (4)
N2—C11—C15102.53 (18)C9—N2—C11112.72 (19)
N3—C11—C15102.93 (18)C9—N2—C7122.0 (2)
C12—C11—C15116.0 (2)C11—N2—C7120.86 (19)
O5—C12—O6126.7 (3)C10—N3—C11112.5 (2)
O5—C12—C11123.8 (3)C10—N3—C8121.0 (2)
O6—C12—C11109.5 (2)C11—N3—C8122.4 (2)
C14—C13—O6110.5 (3)C9—N4—C15111.95 (19)
C14—C13—H13A109.5C9—N4—C19122.4 (2)
O6—C13—H13A109.5C15—N4—C19116.83 (19)
C14—C13—H13B109.5C10—N5—C20120.6 (2)
O6—C13—H13B109.5C10—N5—C15110.65 (19)
H13A—C13—H13B108.1C20—N5—C15115.1 (2)
C13—C14—H14A109.5C12—O6—C13117.7 (2)
C13—C14—H14B109.5C16—O8—C17117.4 (2)
H14A—C14—H14B109.5C19—O9—C20110.9 (2)
C3—C1—C2—C60.3 (4)N3—C11—N2—C757.7 (3)
N1—C1—C2—C6177.7 (2)C12—C11—N2—C768.0 (3)
C2—C1—C3—C40.2 (4)C15—C11—N2—C7168.3 (2)
N1—C1—C3—C4178.2 (3)C6—C7—N2—C974.5 (3)
C1—C3—C4—C50.8 (4)C6—C7—N2—C1180.2 (3)
C3—C4—C5—C60.8 (4)O4—C10—N3—C11169.5 (2)
C3—C4—C5—C8178.8 (3)N5—C10—N3—C1113.8 (3)
C1—C2—C6—C50.2 (4)O4—C10—N3—C811.7 (4)
C1—C2—C6—C7177.0 (2)N5—C10—N3—C8171.6 (2)
C4—C5—C6—C20.3 (4)N2—C11—N3—C10103.8 (2)
C8—C5—C6—C2179.3 (2)C12—C11—N3—C10131.4 (2)
C4—C5—C6—C7177.5 (2)C15—C11—N3—C106.6 (3)
C8—C5—C6—C72.1 (3)N2—C11—N3—C853.6 (3)
C2—C6—C7—N2116.3 (3)C12—C11—N3—C871.2 (3)
C5—C6—C7—N260.9 (3)C15—C11—N3—C8164.0 (2)
C4—C5—C8—N3118.0 (3)C5—C8—N3—C1081.6 (3)
C6—C5—C8—N361.6 (3)C5—C8—N3—C1173.9 (3)
N2—C11—C12—O5123.6 (3)O3—C9—N4—C15174.4 (2)
N3—C11—C12—O53.8 (4)N2—C9—N4—C159.9 (3)
C15—C11—C12—O5121.0 (3)O3—C9—N4—C1928.1 (4)
N2—C11—C12—O654.1 (3)N2—C9—N4—C19156.1 (2)
N3—C11—C12—O6178.5 (2)N5—C15—N4—C9108.2 (2)
C15—C11—C12—O661.3 (3)C16—C15—N4—C9129.1 (2)
N2—C11—C15—N45.0 (2)C11—C15—N4—C92.7 (3)
N3—C11—C15—N4113.9 (2)N5—C15—N4—C1940.1 (3)
C12—C11—C15—N4124.4 (2)C16—C15—N4—C1982.5 (3)
N2—C11—C15—N5121.5 (2)C11—C15—N4—C19151.0 (2)
N3—C11—C15—N52.6 (2)O9—C19—N4—C995.7 (3)
C12—C11—C15—N5119.1 (2)O9—C19—N4—C1549.1 (3)
N2—C11—C15—C16117.6 (2)O4—C10—N5—C2029.2 (4)
N3—C11—C15—C16123.5 (2)N3—C10—N5—C20154.1 (2)
C12—C11—C15—C161.8 (3)O4—C10—N5—C15167.8 (3)
N4—C15—C16—O76.3 (4)N3—C10—N5—C1515.5 (3)
N5—C15—C16—O7117.4 (3)O9—C20—N5—C1085.2 (3)
C11—C15—C16—O7125.0 (3)O9—C20—N5—C1551.7 (3)
N4—C15—C16—O8175.4 (2)N4—C15—N5—C10100.0 (2)
N5—C15—C16—O860.9 (3)C16—C15—N5—C10136.6 (2)
C11—C15—C16—O856.7 (3)C11—C15—N5—C1011.0 (3)
C3—C1—N1—O1170.3 (4)N4—C15—N5—C2041.1 (3)
C2—C1—N1—O111.7 (5)C16—C15—N5—C2082.3 (3)
C3—C1—N1—O26.5 (5)C11—C15—N5—C20152.0 (2)
C2—C1—N1—O2171.5 (4)O5—C12—O6—C130.5 (4)
O3—C9—N2—C11170.6 (2)C11—C12—O6—C13178.1 (2)
N4—C9—N2—C1113.7 (3)C14—C13—O6—C1291.6 (4)
O3—C9—N2—C714.1 (4)O7—C16—O8—C170.7 (4)
N4—C9—N2—C7170.2 (2)C15—C16—O8—C17178.9 (2)
N3—C11—N2—C999.1 (2)C18—C17—O8—C1692.4 (4)
C12—C11—N2—C9135.3 (2)N4—C19—O9—C2057.5 (3)
C15—C11—N2—C911.5 (3)N5—C20—O9—C1959.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C20—H20A···O3i0.972.543.262 (4)132
C19—H19B···O4i0.972.543.444 (4)156
C17—H17A···O7ii0.972.523.293 (5)136
C7—H7B···O3iii0.972.413.288 (3)150
Symmetry codes: (i) x+1, y+1, z+2; (ii) x, y+3/2, z1/2; (iii) x, y+1, z+2.

Experimental details

Crystal data
Chemical formulaC20H21N5O9
Mr475.42
Crystal system, space groupMonoclinic, P21/c
Temperature (K)292
a, b, c (Å)10.0454 (18), 25.564 (5), 8.4997 (15)
β (°) 99.427 (3)
V3)2153.2 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1997)
Tmin, Tmax0.966, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
11538, 4225, 3284
Rint0.053
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.065, 0.172, 1.05
No. of reflections4225
No. of parameters309
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.48, 0.32

Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXTL.

Selected geometric parameters (Å, º) top
C1—N11.462 (5)C11—N21.441 (3)
C9—O31.205 (3)C11—N31.444 (3)
C9—N21.374 (3)C11—C151.566 (3)
C9—N41.384 (3)C15—N41.443 (3)
C10—O41.211 (3)C15—N51.458 (3)
C10—N31.372 (3)C19—O91.415 (3)
C10—N51.385 (3)C20—O91.417 (3)
N2—C7—C6111.93 (19)N2—C11—N3114.3 (2)
N3—C8—C5113.6 (2)N4—C15—N5111.5 (2)
N2—C9—N4107.5 (2)C19—O9—C20110.9 (2)
N3—C10—N5108.2 (2)
C6—C7—N2—C974.5 (3)C5—C8—N3—C1081.6 (3)
C6—C7—N2—C1180.2 (3)C5—C8—N3—C1173.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C20—H20A···O3i0.972.543.262 (4)132
C19—H19B···O4i0.972.543.444 (4)156
C17—H17A···O7ii0.972.523.293 (5)136
C7—H7B···O3iii0.972.413.288 (3)150
Symmetry codes: (i) x+1, y+1, z+2; (ii) x, y+3/2, z1/2; (iii) x, y+1, z+2.
 

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