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In the title compound, C20H21BrN4O2, the pyrrolopyrimidine ring system is essentially planar. The bromo­phenyl ring forms a dihedral angle of 33.1 (1)° with the pyrrolopyrimidine ring system. C—H...N hydrogen bonds link the mol­ecules into cyclic centrosymmetric R22(18) dimers, which are crosslinked along the [\overline{1}10] direction through C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045692/ci2465sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045692/ci2465Isup2.hkl
Contains datablock I

CCDC reference: 663800

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.042
  • wR factor = 0.147
  • Data-to-parameter ratio = 29.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 0 ALERT type 5 Informative message, check

Comment top

Pyrrolo[2,3-d]pyrimidines are an important class of compounds that are structurally and chemically related to nucleosides and some antibiotics (Oghi et al., 1979; Tolman et al., 1968). The well known biological activity of these compounds has led to intense investigation of their use as antitumor, anti-allergic, antiviral and anti-inflammatory agents (Hutzenlaub et al., 1972; Smith et al., 1972). In view of this biological importance, the crystal structure of the title compound has been determined and the results are presnted here.

In the title molecule (Fig. 1) the pyrrolopyrimidine ring system is essentially planar, with a maximum deviation of 0.059 (2) Å for atom N3. The keto atoms O1 and O2 deviate by 0.125 (2) and 0.057 (2) Å, respectively, from the pyrimidine ring. The bromophenyl ring forms a dihedral angle of 33.1 (1)° with the pyrrolopyrimidine ring system. The Br atom deviates from the plane of the attached ring by 0.047 (1) Å.

The crystal packing is stabilized by C—H···O and C—H···N type hydrogen bonds (Table 1). Atom C20 in the molecule at (x, y, z) donate one proton to atom O1 at (-1 + x, 1 + y, z) forming a zig zag chain C(11) along the [1 1 0] direction. The molecules at (x, y, z) and (1 - x, -y, -z) are linked by C8—H8A···N1 hydrogen bonds into cyclic centrosymmetric R22(18) dimers.

Related literature top

For biological activities of pyrrolo[2,3-d]pyrimidine compounds, see: Hutzenlaub et al. (1972); Oghi et al. (1979); Smith et al. (1972); Tolman et al. (1968).

Experimental top

A mixture of 1,3-dimethyl-7-(3-methyl-but-2-enyl)-2,4-dioxo-1H-pyrrole (2,3 - d)pyrmidine-6-carbaldehyde (1 mmol) and p-bromoaniline (1 mmol) was refluxed in ethanol (10 ml) for 2 h. After cooling the solution, the precipitate formed was filtered off and washed with ethanol to give a pure yellow solid. Single crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.

Refinement top

H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). A rotating group model was used for the methyl groups.

Structure description top

Pyrrolo[2,3-d]pyrimidines are an important class of compounds that are structurally and chemically related to nucleosides and some antibiotics (Oghi et al., 1979; Tolman et al., 1968). The well known biological activity of these compounds has led to intense investigation of their use as antitumor, anti-allergic, antiviral and anti-inflammatory agents (Hutzenlaub et al., 1972; Smith et al., 1972). In view of this biological importance, the crystal structure of the title compound has been determined and the results are presnted here.

In the title molecule (Fig. 1) the pyrrolopyrimidine ring system is essentially planar, with a maximum deviation of 0.059 (2) Å for atom N3. The keto atoms O1 and O2 deviate by 0.125 (2) and 0.057 (2) Å, respectively, from the pyrimidine ring. The bromophenyl ring forms a dihedral angle of 33.1 (1)° with the pyrrolopyrimidine ring system. The Br atom deviates from the plane of the attached ring by 0.047 (1) Å.

The crystal packing is stabilized by C—H···O and C—H···N type hydrogen bonds (Table 1). Atom C20 in the molecule at (x, y, z) donate one proton to atom O1 at (-1 + x, 1 + y, z) forming a zig zag chain C(11) along the [1 1 0] direction. The molecules at (x, y, z) and (1 - x, -y, -z) are linked by C8—H8A···N1 hydrogen bonds into cyclic centrosymmetric R22(18) dimers.

For biological activities of pyrrolo[2,3-d]pyrimidine compounds, see: Hutzenlaub et al. (1972); Oghi et al. (1979); Smith et al. (1972); Tolman et al. (1968).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
6-[(4-Bromophenyl)iminomethyl]-1,3-dimethyl-7-(2-methylpropenyl)-1,2,3,4- tetrahydro-7H-pyrrolo[2,3-d]pyrimidine-2,4-dione top
Crystal data top
C20H21BrN4O2Z = 2
Mr = 429.32F(000) = 440
Triclinic, P1Dx = 1.512 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.202 (3) ÅCell parameters from 4856 reflections
b = 9.989 (3) Åθ = 2–33.7°
c = 10.454 (4) ŵ = 2.20 mm1
α = 87.363 (19)°T = 293 K
β = 80.67 (2)°Block, yellow
γ = 84.187 (19)°0.25 × 0.20 × 0.18 mm
V = 942.9 (6) Å3
Data collection top
Bruker APEXII CCD area-detector
diffractometer
7255 independent reflections
Radiation source: fine-focus sealed tube4235 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ω and φ scansθmax = 33.7°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 1414
Tmin = 0.595, Tmax = 0.673k = 1515
25023 measured reflectionsl = 1416
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.077P)2 + 0.1592P]
where P = (Fo2 + 2Fc2)/3
7255 reflections(Δ/σ)max = 0.001
248 parametersΔρmax = 1.05 e Å3
0 restraintsΔρmin = 0.68 e Å3
Crystal data top
C20H21BrN4O2γ = 84.187 (19)°
Mr = 429.32V = 942.9 (6) Å3
Triclinic, P1Z = 2
a = 9.202 (3) ÅMo Kα radiation
b = 9.989 (3) ŵ = 2.20 mm1
c = 10.454 (4) ÅT = 293 K
α = 87.363 (19)°0.25 × 0.20 × 0.18 mm
β = 80.67 (2)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
7255 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
4235 reflections with I > 2σ(I)
Tmin = 0.595, Tmax = 0.673Rint = 0.036
25023 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.147H-atom parameters constrained
S = 1.01Δρmax = 1.05 e Å3
7255 reflectionsΔρmin = 0.68 e Å3
248 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
Br0.31222 (3)0.56793 (3)0.43672 (2)0.06218 (12)
O10.49380 (19)0.31916 (16)0.03864 (18)0.0537 (4)
O20.5675 (2)0.1746 (2)0.34797 (19)0.0676 (5)
N10.04816 (19)0.25040 (18)0.06728 (17)0.0402 (4)
N20.24412 (17)0.08034 (16)0.10161 (16)0.0341 (3)
N30.51882 (19)0.25241 (18)0.1613 (2)0.0444 (4)
N40.41031 (19)0.03963 (18)0.24052 (17)0.0394 (4)
C10.2032 (2)0.05049 (19)0.01682 (19)0.0357 (4)
C20.2768 (2)0.07013 (19)0.05594 (19)0.0387 (4)
H20.27010.11330.13140.046*
C30.3637 (2)0.11688 (19)0.03721 (19)0.0355 (4)
C40.4618 (2)0.2366 (2)0.0448 (2)0.0397 (4)
C50.5032 (2)0.1569 (2)0.2555 (2)0.0463 (5)
C60.3406 (2)0.02355 (19)0.13358 (18)0.0332 (4)
C70.1079 (2)0.1321 (2)0.0913 (2)0.0383 (4)
H70.08770.09420.16540.046*
C80.6116 (3)0.3776 (3)0.1821 (3)0.0595 (6)
H8A0.71290.36620.14730.089*
H8B0.57930.44960.13930.089*
H8C0.60320.39880.27340.089*
C90.4161 (3)0.0690 (3)0.3280 (2)0.0518 (5)
H9A0.44930.14650.27840.078*
H9B0.48360.04010.38710.078*
H9C0.31930.09170.37600.078*
C100.1651 (2)0.18875 (19)0.18428 (19)0.0371 (4)
H10A0.12070.25820.13090.045*
H10B0.23470.22900.22770.045*
C110.0472 (2)0.1348 (2)0.2832 (2)0.0414 (4)
H110.07000.05140.32220.050*
C120.0866 (2)0.1957 (2)0.3201 (2)0.0453 (5)
C130.1929 (3)0.1296 (4)0.4228 (3)0.0716 (8)
H13A0.15010.04150.44430.107*
H13B0.28360.12220.39060.107*
H13C0.21260.18300.49880.107*
C140.1424 (3)0.3286 (3)0.2669 (3)0.0596 (6)
H14A0.07190.35630.19500.089*
H14B0.15600.39420.33320.089*
H14C0.23510.32090.23830.089*
C150.1998 (2)0.4639 (2)0.3244 (2)0.0413 (4)
C160.0756 (3)0.3820 (2)0.3740 (2)0.0469 (5)
H160.04760.37550.46320.056*
C170.0068 (2)0.3100 (2)0.2911 (2)0.0441 (5)
H170.09060.25500.32480.053*
C180.0334 (2)0.3183 (2)0.15775 (19)0.0369 (4)
C190.1572 (2)0.4033 (2)0.1098 (2)0.0412 (4)
H190.18370.41180.02070.049*
C200.2421 (2)0.4754 (2)0.1920 (2)0.0416 (4)
H200.32600.53060.15880.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br0.06096 (17)0.0752 (2)0.04937 (16)0.01901 (12)0.02074 (12)0.00422 (12)
O10.0550 (9)0.0442 (8)0.0581 (10)0.0067 (7)0.0018 (8)0.0130 (7)
O20.0726 (12)0.0725 (12)0.0623 (12)0.0100 (10)0.0351 (10)0.0007 (10)
N10.0431 (9)0.0411 (9)0.0366 (9)0.0006 (7)0.0089 (7)0.0002 (7)
N20.0369 (8)0.0329 (8)0.0325 (8)0.0030 (6)0.0053 (6)0.0026 (6)
N30.0374 (8)0.0386 (9)0.0562 (11)0.0003 (7)0.0076 (8)0.0026 (8)
N40.0402 (8)0.0421 (9)0.0368 (9)0.0023 (7)0.0089 (7)0.0039 (7)
C10.0384 (9)0.0332 (9)0.0364 (10)0.0060 (7)0.0069 (7)0.0020 (7)
C20.0454 (10)0.0362 (10)0.0354 (10)0.0054 (8)0.0066 (8)0.0051 (8)
C30.0366 (9)0.0316 (9)0.0376 (10)0.0036 (7)0.0025 (7)0.0043 (7)
C40.0344 (9)0.0356 (9)0.0468 (11)0.0028 (7)0.0006 (8)0.0007 (8)
C50.0397 (10)0.0486 (12)0.0506 (13)0.0021 (9)0.0103 (9)0.0057 (10)
C60.0329 (8)0.0340 (9)0.0328 (9)0.0049 (7)0.0042 (7)0.0012 (7)
C70.0409 (10)0.0386 (10)0.0371 (10)0.0067 (8)0.0096 (8)0.0007 (8)
C80.0475 (12)0.0471 (13)0.0834 (19)0.0064 (10)0.0178 (12)0.0070 (12)
C90.0542 (13)0.0599 (14)0.0454 (12)0.0036 (11)0.0182 (10)0.0120 (11)
C100.0406 (9)0.0336 (9)0.0371 (10)0.0017 (7)0.0053 (8)0.0073 (8)
C110.0443 (10)0.0470 (11)0.0331 (10)0.0031 (8)0.0072 (8)0.0018 (8)
C120.0423 (10)0.0605 (13)0.0343 (10)0.0052 (9)0.0062 (8)0.0130 (9)
C130.0525 (14)0.107 (2)0.0539 (16)0.0189 (15)0.0031 (12)0.0057 (16)
C140.0554 (14)0.0665 (16)0.0545 (14)0.0128 (11)0.0081 (11)0.0194 (12)
C150.0417 (10)0.0429 (10)0.0405 (11)0.0006 (8)0.0123 (8)0.0035 (8)
C160.0520 (12)0.0543 (13)0.0328 (10)0.0060 (10)0.0067 (9)0.0070 (9)
C170.0434 (10)0.0480 (11)0.0380 (11)0.0072 (8)0.0043 (8)0.0051 (9)
C180.0379 (9)0.0373 (9)0.0362 (10)0.0040 (7)0.0081 (7)0.0011 (8)
C190.0448 (10)0.0426 (10)0.0346 (10)0.0005 (8)0.0031 (8)0.0030 (8)
C200.0370 (9)0.0417 (10)0.0443 (11)0.0019 (8)0.0033 (8)0.0048 (9)
Geometric parameters (Å, º) top
Br—C151.895 (2)C9—H9B0.96
O1—C41.209 (3)C9—H9C0.96
O2—C51.210 (3)C10—C111.497 (3)
N1—C71.270 (3)C10—H10A0.97
N1—C181.409 (3)C10—H10B0.97
N2—C61.362 (3)C11—C121.324 (3)
N2—C11.404 (3)C11—H110.93
N2—C101.473 (2)C12—C141.490 (4)
N3—C51.383 (3)C12—C131.507 (4)
N3—C41.399 (3)C13—H13A0.96
N3—C81.469 (3)C13—H13B0.96
N4—C61.372 (3)C13—H13C0.96
N4—C51.397 (3)C14—H14A0.96
N4—C91.461 (3)C14—H14B0.96
C1—C21.367 (3)C14—H14C0.96
C1—C71.435 (3)C15—C161.380 (3)
C2—C31.393 (3)C15—C201.383 (3)
C2—H20.93C16—C171.374 (3)
C3—C61.381 (3)C16—H160.93
C3—C41.431 (3)C17—C181.387 (3)
C7—H70.93C17—H170.93
C8—H8A0.96C18—C191.389 (3)
C8—H8B0.96C19—C201.383 (3)
C8—H8C0.96C19—H190.93
C9—H9A0.96C20—H200.93
C7—N1—C18118.68 (18)N2—C10—C11110.60 (16)
C6—N2—C1107.35 (15)N2—C10—H10A109.5
C6—N2—C10128.39 (17)C11—C10—H10A109.5
C1—N2—C10122.74 (16)N2—C10—H10B109.5
C5—N3—C4125.68 (18)C11—C10—H10B109.5
C5—N3—C8116.8 (2)H10A—C10—H10B108.1
C4—N3—C8117.4 (2)C12—C11—C10125.6 (2)
C6—N4—C5119.08 (18)C12—C11—H11117.2
C6—N4—C9123.49 (18)C10—C11—H11117.2
C5—N4—C9116.40 (18)C11—C12—C14124.4 (2)
C2—C1—N2108.19 (18)C11—C12—C13119.5 (2)
C2—C1—C7123.93 (19)C14—C12—C13116.1 (2)
N2—C1—C7127.80 (18)C12—C13—H13A109.5
C1—C2—C3107.90 (18)C12—C13—H13B109.5
C1—C2—H2126.0H13A—C13—H13B109.5
C3—C2—H2126.0C12—C13—H13C109.5
C2—C3—C6107.51 (17)H13A—C13—H13C109.5
C2—C3—C4131.28 (18)H13B—C13—H13C109.5
C6—C3—C4121.21 (19)C12—C14—H14A109.5
O1—C4—N3121.5 (2)C12—C14—H14B109.5
O1—C4—C3125.0 (2)H14A—C14—H14B109.5
N3—C4—C3113.50 (18)C12—C14—H14C109.5
O2—C5—N3121.1 (2)H14A—C14—H14C109.5
O2—C5—N4121.2 (2)H14B—C14—H14C109.5
N3—C5—N4117.76 (19)C16—C15—C20120.8 (2)
N2—C6—N4128.68 (17)C16—C15—Br120.57 (17)
N2—C6—C3109.05 (17)C20—C15—Br118.62 (16)
N4—C6—C3122.26 (18)C17—C16—C15119.8 (2)
N1—C7—C1127.14 (19)C17—C16—H16120.1
N1—C7—H7116.4C15—C16—H16120.1
C1—C7—H7116.4C16—C17—C18120.89 (19)
N3—C8—H8A109.5C16—C17—H17119.6
N3—C8—H8B109.5C18—C17—H17119.6
H8A—C8—H8B109.5C19—C18—C17118.45 (19)
N3—C8—H8C109.5C19—C18—N1117.60 (18)
H8A—C8—H8C109.5C17—C18—N1123.88 (18)
H8B—C8—H8C109.5C18—C19—C20121.3 (2)
N4—C9—H9A109.5C18—C19—H19119.3
N4—C9—H9B109.5C20—C19—H19119.3
H9A—C9—H9B109.5C19—C20—C15118.77 (19)
N4—C9—H9C109.5C19—C20—H20120.6
H9A—C9—H9C109.5C15—C20—H20120.6
H9B—C9—H9C109.5
C6—N2—C1—C20.8 (2)C5—N4—C6—N2178.48 (19)
C10—N2—C1—C2167.79 (17)C9—N4—C6—N213.6 (3)
C6—N2—C1—C7177.54 (19)C5—N4—C6—C32.7 (3)
C10—N2—C1—C715.5 (3)C9—N4—C6—C3165.21 (19)
N2—C1—C2—C30.2 (2)C2—C3—C6—N21.0 (2)
C7—C1—C2—C3177.07 (18)C4—C3—C6—N2179.45 (17)
C1—C2—C3—C60.5 (2)C2—C3—C6—N4179.97 (17)
C1—C2—C3—C4180.0 (2)C4—C3—C6—N40.4 (3)
C5—N3—C4—O1171.9 (2)C18—N1—C7—C1175.24 (19)
C8—N3—C4—O13.9 (3)C2—C1—C7—N1172.4 (2)
C5—N3—C4—C38.8 (3)N2—C1—C7—N13.8 (3)
C8—N3—C4—C3175.42 (19)C6—N2—C10—C1171.1 (2)
C2—C3—C4—O14.8 (4)C1—N2—C10—C1193.0 (2)
C6—C3—C4—O1175.78 (19)N2—C10—C11—C12139.8 (2)
C2—C3—C4—N3174.5 (2)C10—C11—C12—C140.8 (3)
C6—C3—C4—N34.9 (3)C10—C11—C12—C13179.0 (2)
C4—N3—C5—O2173.2 (2)C20—C15—C16—C170.5 (4)
C8—N3—C5—O22.6 (3)Br—C15—C16—C17178.26 (18)
C4—N3—C5—N46.9 (3)C15—C16—C17—C180.1 (4)
C8—N3—C5—N4177.27 (19)C16—C17—C18—C191.3 (3)
C6—N4—C5—O2179.5 (2)C16—C17—C18—N1178.1 (2)
C9—N4—C5—O210.7 (3)C7—N1—C18—C19145.2 (2)
C6—N4—C5—N30.7 (3)C7—N1—C18—C1738.0 (3)
C9—N4—C5—N3169.48 (19)C17—C18—C19—C201.9 (3)
C1—N2—C6—N4179.96 (18)N1—C18—C19—C20178.96 (18)
C10—N2—C6—N413.9 (3)C18—C19—C20—C151.3 (3)
C1—N2—C6—C31.1 (2)C16—C15—C20—C190.1 (3)
C10—N2—C6—C3167.14 (17)Br—C15—C20—C19177.71 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8A···N1i0.962.593.508 (3)160
C9—H9B···O20.962.242.695 (3)108
C10—H10A···N10.972.283.015 (3)131
C20—H20···O1ii0.932.363.274 (3)167
Symmetry codes: (i) x+1, y, z; (ii) x1, y+1, z.

Experimental details

Crystal data
Chemical formulaC20H21BrN4O2
Mr429.32
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)9.202 (3), 9.989 (3), 10.454 (4)
α, β, γ (°)87.363 (19), 80.67 (2), 84.187 (19)
V3)942.9 (6)
Z2
Radiation typeMo Kα
µ (mm1)2.20
Crystal size (mm)0.25 × 0.20 × 0.18
Data collection
DiffractometerBruker APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2001)
Tmin, Tmax0.595, 0.673
No. of measured, independent and
observed [I > 2σ(I)] reflections
25023, 7255, 4235
Rint0.036
(sin θ/λ)max1)0.781
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.147, 1.01
No. of reflections7255
No. of parameters248
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.05, 0.68

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 1997), ZORTEP (Zsolnai, 1997), SHELXL97 (Sheldrick, 1997) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8A···N1i0.962.593.508 (3)160
C9—H9B···O20.962.242.695 (3)108
C10—H10A···N10.972.283.015 (3)131
C20—H20···O1ii0.932.363.274 (3)167
Symmetry codes: (i) x+1, y, z; (ii) x1, y+1, z.
 

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