Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045692/ci2465sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045692/ci2465Isup2.hkl |
CCDC reference: 663800
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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).
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.
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.
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).
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).
C20H21BrN4O2 | Z = 2 |
Mr = 429.32 | F(000) = 440 |
Triclinic, P1 | Dx = 1.512 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.202 (3) Å | Cell parameters from 4856 reflections |
b = 9.989 (3) Å | θ = 2–33.7° |
c = 10.454 (4) Å | µ = 2.20 mm−1 |
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 |
Bruker APEXII CCD area-detector diffractometer | 7255 independent reflections |
Radiation source: fine-focus sealed tube | 4235 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
ω and φ scans | θmax = 33.7°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −14→14 |
Tmin = 0.595, Tmax = 0.673 | k = −15→15 |
25023 measured reflections | l = −14→16 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.147 | H-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 parameters | Δρmax = 1.05 e Å−3 |
0 restraints | Δρmin = −0.68 e Å−3 |
C20H21BrN4O2 | γ = 84.187 (19)° |
Mr = 429.32 | V = 942.9 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.202 (3) Å | Mo Kα radiation |
b = 9.989 (3) Å | µ = 2.20 mm−1 |
c = 10.454 (4) Å | T = 293 K |
α = 87.363 (19)° | 0.25 × 0.20 × 0.18 mm |
β = 80.67 (2)° |
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 = 0.673 | Rint = 0.036 |
25023 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.147 | H-atom parameters constrained |
S = 1.01 | Δρmax = 1.05 e Å−3 |
7255 reflections | Δρmin = −0.68 e Å−3 |
248 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Br | −0.31222 (3) | 0.56793 (3) | −0.43672 (2) | 0.06218 (12) | |
O1 | 0.49380 (19) | −0.31916 (16) | −0.03864 (18) | 0.0537 (4) | |
O2 | 0.5675 (2) | −0.1746 (2) | 0.34797 (19) | 0.0676 (5) | |
N1 | 0.04816 (19) | 0.25040 (18) | −0.06728 (17) | 0.0402 (4) | |
N2 | 0.24412 (17) | 0.08034 (16) | 0.10161 (16) | 0.0341 (3) | |
N3 | 0.51882 (19) | −0.25241 (18) | 0.1613 (2) | 0.0444 (4) | |
N4 | 0.41031 (19) | −0.03963 (18) | 0.24052 (17) | 0.0394 (4) | |
C1 | 0.2032 (2) | 0.05049 (19) | −0.01682 (19) | 0.0357 (4) | |
C2 | 0.2768 (2) | −0.07013 (19) | −0.05594 (19) | 0.0387 (4) | |
H2 | 0.2701 | −0.1133 | −0.1314 | 0.046* | |
C3 | 0.3637 (2) | −0.11688 (19) | 0.03721 (19) | 0.0355 (4) | |
C4 | 0.4618 (2) | −0.2366 (2) | 0.0448 (2) | 0.0397 (4) | |
C5 | 0.5032 (2) | −0.1569 (2) | 0.2555 (2) | 0.0463 (5) | |
C6 | 0.3406 (2) | −0.02355 (19) | 0.13358 (18) | 0.0332 (4) | |
C7 | 0.1079 (2) | 0.1321 (2) | −0.0913 (2) | 0.0383 (4) | |
H7 | 0.0877 | 0.0942 | −0.1654 | 0.046* | |
C8 | 0.6116 (3) | −0.3776 (3) | 0.1821 (3) | 0.0595 (6) | |
H8A | 0.7129 | −0.3662 | 0.1473 | 0.089* | |
H8B | 0.5793 | −0.4496 | 0.1393 | 0.089* | |
H8C | 0.6032 | −0.3988 | 0.2734 | 0.089* | |
C9 | 0.4161 (3) | 0.0690 (3) | 0.3280 (2) | 0.0518 (5) | |
H9A | 0.4493 | 0.1465 | 0.2784 | 0.078* | |
H9B | 0.4836 | 0.0401 | 0.3871 | 0.078* | |
H9C | 0.3193 | 0.0917 | 0.3760 | 0.078* | |
C10 | 0.1651 (2) | 0.18875 (19) | 0.18428 (19) | 0.0371 (4) | |
H10A | 0.1207 | 0.2582 | 0.1309 | 0.045* | |
H10B | 0.2347 | 0.2290 | 0.2277 | 0.045* | |
C11 | 0.0472 (2) | 0.1348 (2) | 0.2832 (2) | 0.0414 (4) | |
H11 | 0.0700 | 0.0514 | 0.3222 | 0.050* | |
C12 | −0.0866 (2) | 0.1957 (2) | 0.3201 (2) | 0.0453 (5) | |
C13 | −0.1929 (3) | 0.1296 (4) | 0.4228 (3) | 0.0716 (8) | |
H13A | −0.1501 | 0.0415 | 0.4443 | 0.107* | |
H13B | −0.2836 | 0.1222 | 0.3906 | 0.107* | |
H13C | −0.2126 | 0.1830 | 0.4988 | 0.107* | |
C14 | −0.1424 (3) | 0.3286 (3) | 0.2669 (3) | 0.0596 (6) | |
H14A | −0.0719 | 0.3563 | 0.1950 | 0.089* | |
H14B | −0.1560 | 0.3942 | 0.3332 | 0.089* | |
H14C | −0.2351 | 0.3209 | 0.2383 | 0.089* | |
C15 | −0.1998 (2) | 0.4639 (2) | −0.3244 (2) | 0.0413 (4) | |
C16 | −0.0756 (3) | 0.3820 (2) | −0.3740 (2) | 0.0469 (5) | |
H16 | −0.0476 | 0.3755 | −0.4632 | 0.056* | |
C17 | 0.0068 (2) | 0.3100 (2) | −0.2911 (2) | 0.0441 (5) | |
H17 | 0.0906 | 0.2550 | −0.3248 | 0.053* | |
C18 | −0.0334 (2) | 0.3183 (2) | −0.15775 (19) | 0.0369 (4) | |
C19 | −0.1572 (2) | 0.4033 (2) | −0.1098 (2) | 0.0412 (4) | |
H19 | −0.1837 | 0.4118 | −0.0207 | 0.049* | |
C20 | −0.2421 (2) | 0.4754 (2) | −0.1920 (2) | 0.0416 (4) | |
H20 | −0.3260 | 0.5306 | −0.1588 | 0.050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br | 0.06096 (17) | 0.0752 (2) | 0.04937 (16) | 0.01901 (12) | −0.02074 (12) | −0.00422 (12) |
O1 | 0.0550 (9) | 0.0442 (8) | 0.0581 (10) | 0.0067 (7) | −0.0018 (8) | −0.0130 (7) |
O2 | 0.0726 (12) | 0.0725 (12) | 0.0623 (12) | 0.0100 (10) | −0.0351 (10) | −0.0007 (10) |
N1 | 0.0431 (9) | 0.0411 (9) | 0.0366 (9) | −0.0006 (7) | −0.0089 (7) | 0.0002 (7) |
N2 | 0.0369 (8) | 0.0329 (8) | 0.0325 (8) | −0.0030 (6) | −0.0053 (6) | −0.0026 (6) |
N3 | 0.0374 (8) | 0.0386 (9) | 0.0562 (11) | −0.0003 (7) | −0.0076 (8) | 0.0026 (8) |
N4 | 0.0402 (8) | 0.0421 (9) | 0.0368 (9) | −0.0023 (7) | −0.0089 (7) | −0.0039 (7) |
C1 | 0.0384 (9) | 0.0332 (9) | 0.0364 (10) | −0.0060 (7) | −0.0069 (7) | −0.0020 (7) |
C2 | 0.0454 (10) | 0.0362 (10) | 0.0354 (10) | −0.0054 (8) | −0.0066 (8) | −0.0051 (8) |
C3 | 0.0366 (9) | 0.0316 (9) | 0.0376 (10) | −0.0036 (7) | −0.0025 (7) | −0.0043 (7) |
C4 | 0.0344 (9) | 0.0356 (9) | 0.0468 (11) | −0.0028 (7) | −0.0006 (8) | −0.0007 (8) |
C5 | 0.0397 (10) | 0.0486 (12) | 0.0506 (13) | −0.0021 (9) | −0.0103 (9) | 0.0057 (10) |
C6 | 0.0329 (8) | 0.0340 (9) | 0.0328 (9) | −0.0049 (7) | −0.0042 (7) | −0.0012 (7) |
C7 | 0.0409 (10) | 0.0386 (10) | 0.0371 (10) | −0.0067 (8) | −0.0096 (8) | −0.0007 (8) |
C8 | 0.0475 (12) | 0.0471 (13) | 0.0834 (19) | 0.0064 (10) | −0.0178 (12) | 0.0070 (12) |
C9 | 0.0542 (13) | 0.0599 (14) | 0.0454 (12) | −0.0036 (11) | −0.0182 (10) | −0.0120 (11) |
C10 | 0.0406 (9) | 0.0336 (9) | 0.0371 (10) | −0.0017 (7) | −0.0053 (8) | −0.0073 (8) |
C11 | 0.0443 (10) | 0.0470 (11) | 0.0331 (10) | −0.0031 (8) | −0.0072 (8) | −0.0018 (8) |
C12 | 0.0423 (10) | 0.0605 (13) | 0.0343 (10) | −0.0052 (9) | −0.0062 (8) | −0.0130 (9) |
C13 | 0.0525 (14) | 0.107 (2) | 0.0539 (16) | −0.0189 (15) | 0.0031 (12) | −0.0057 (16) |
C14 | 0.0554 (14) | 0.0665 (16) | 0.0545 (14) | 0.0128 (11) | −0.0081 (11) | −0.0194 (12) |
C15 | 0.0417 (10) | 0.0429 (10) | 0.0405 (11) | 0.0006 (8) | −0.0123 (8) | −0.0035 (8) |
C16 | 0.0520 (12) | 0.0543 (13) | 0.0328 (10) | 0.0060 (10) | −0.0067 (9) | −0.0070 (9) |
C17 | 0.0434 (10) | 0.0480 (11) | 0.0380 (11) | 0.0072 (8) | −0.0043 (8) | −0.0051 (9) |
C18 | 0.0379 (9) | 0.0373 (9) | 0.0362 (10) | −0.0040 (7) | −0.0081 (7) | −0.0011 (8) |
C19 | 0.0448 (10) | 0.0426 (10) | 0.0346 (10) | −0.0005 (8) | −0.0031 (8) | −0.0030 (8) |
C20 | 0.0370 (9) | 0.0417 (10) | 0.0443 (11) | 0.0019 (8) | −0.0033 (8) | −0.0048 (9) |
Br—C15 | 1.895 (2) | C9—H9B | 0.96 |
O1—C4 | 1.209 (3) | C9—H9C | 0.96 |
O2—C5 | 1.210 (3) | C10—C11 | 1.497 (3) |
N1—C7 | 1.270 (3) | C10—H10A | 0.97 |
N1—C18 | 1.409 (3) | C10—H10B | 0.97 |
N2—C6 | 1.362 (3) | C11—C12 | 1.324 (3) |
N2—C1 | 1.404 (3) | C11—H11 | 0.93 |
N2—C10 | 1.473 (2) | C12—C14 | 1.490 (4) |
N3—C5 | 1.383 (3) | C12—C13 | 1.507 (4) |
N3—C4 | 1.399 (3) | C13—H13A | 0.96 |
N3—C8 | 1.469 (3) | C13—H13B | 0.96 |
N4—C6 | 1.372 (3) | C13—H13C | 0.96 |
N4—C5 | 1.397 (3) | C14—H14A | 0.96 |
N4—C9 | 1.461 (3) | C14—H14B | 0.96 |
C1—C2 | 1.367 (3) | C14—H14C | 0.96 |
C1—C7 | 1.435 (3) | C15—C16 | 1.380 (3) |
C2—C3 | 1.393 (3) | C15—C20 | 1.383 (3) |
C2—H2 | 0.93 | C16—C17 | 1.374 (3) |
C3—C6 | 1.381 (3) | C16—H16 | 0.93 |
C3—C4 | 1.431 (3) | C17—C18 | 1.387 (3) |
C7—H7 | 0.93 | C17—H17 | 0.93 |
C8—H8A | 0.96 | C18—C19 | 1.389 (3) |
C8—H8B | 0.96 | C19—C20 | 1.383 (3) |
C8—H8C | 0.96 | C19—H19 | 0.93 |
C9—H9A | 0.96 | C20—H20 | 0.93 |
C7—N1—C18 | 118.68 (18) | N2—C10—C11 | 110.60 (16) |
C6—N2—C1 | 107.35 (15) | N2—C10—H10A | 109.5 |
C6—N2—C10 | 128.39 (17) | C11—C10—H10A | 109.5 |
C1—N2—C10 | 122.74 (16) | N2—C10—H10B | 109.5 |
C5—N3—C4 | 125.68 (18) | C11—C10—H10B | 109.5 |
C5—N3—C8 | 116.8 (2) | H10A—C10—H10B | 108.1 |
C4—N3—C8 | 117.4 (2) | C12—C11—C10 | 125.6 (2) |
C6—N4—C5 | 119.08 (18) | C12—C11—H11 | 117.2 |
C6—N4—C9 | 123.49 (18) | C10—C11—H11 | 117.2 |
C5—N4—C9 | 116.40 (18) | C11—C12—C14 | 124.4 (2) |
C2—C1—N2 | 108.19 (18) | C11—C12—C13 | 119.5 (2) |
C2—C1—C7 | 123.93 (19) | C14—C12—C13 | 116.1 (2) |
N2—C1—C7 | 127.80 (18) | C12—C13—H13A | 109.5 |
C1—C2—C3 | 107.90 (18) | C12—C13—H13B | 109.5 |
C1—C2—H2 | 126.0 | H13A—C13—H13B | 109.5 |
C3—C2—H2 | 126.0 | C12—C13—H13C | 109.5 |
C2—C3—C6 | 107.51 (17) | H13A—C13—H13C | 109.5 |
C2—C3—C4 | 131.28 (18) | H13B—C13—H13C | 109.5 |
C6—C3—C4 | 121.21 (19) | C12—C14—H14A | 109.5 |
O1—C4—N3 | 121.5 (2) | C12—C14—H14B | 109.5 |
O1—C4—C3 | 125.0 (2) | H14A—C14—H14B | 109.5 |
N3—C4—C3 | 113.50 (18) | C12—C14—H14C | 109.5 |
O2—C5—N3 | 121.1 (2) | H14A—C14—H14C | 109.5 |
O2—C5—N4 | 121.2 (2) | H14B—C14—H14C | 109.5 |
N3—C5—N4 | 117.76 (19) | C16—C15—C20 | 120.8 (2) |
N2—C6—N4 | 128.68 (17) | C16—C15—Br | 120.57 (17) |
N2—C6—C3 | 109.05 (17) | C20—C15—Br | 118.62 (16) |
N4—C6—C3 | 122.26 (18) | C17—C16—C15 | 119.8 (2) |
N1—C7—C1 | 127.14 (19) | C17—C16—H16 | 120.1 |
N1—C7—H7 | 116.4 | C15—C16—H16 | 120.1 |
C1—C7—H7 | 116.4 | C16—C17—C18 | 120.89 (19) |
N3—C8—H8A | 109.5 | C16—C17—H17 | 119.6 |
N3—C8—H8B | 109.5 | C18—C17—H17 | 119.6 |
H8A—C8—H8B | 109.5 | C19—C18—C17 | 118.45 (19) |
N3—C8—H8C | 109.5 | C19—C18—N1 | 117.60 (18) |
H8A—C8—H8C | 109.5 | C17—C18—N1 | 123.88 (18) |
H8B—C8—H8C | 109.5 | C18—C19—C20 | 121.3 (2) |
N4—C9—H9A | 109.5 | C18—C19—H19 | 119.3 |
N4—C9—H9B | 109.5 | C20—C19—H19 | 119.3 |
H9A—C9—H9B | 109.5 | C19—C20—C15 | 118.77 (19) |
N4—C9—H9C | 109.5 | C19—C20—H20 | 120.6 |
H9A—C9—H9C | 109.5 | C15—C20—H20 | 120.6 |
H9B—C9—H9C | 109.5 | ||
C6—N2—C1—C2 | −0.8 (2) | C5—N4—C6—N2 | 178.48 (19) |
C10—N2—C1—C2 | −167.79 (17) | C9—N4—C6—N2 | −13.6 (3) |
C6—N2—C1—C7 | −177.54 (19) | C5—N4—C6—C3 | −2.7 (3) |
C10—N2—C1—C7 | 15.5 (3) | C9—N4—C6—C3 | 165.21 (19) |
N2—C1—C2—C3 | 0.2 (2) | C2—C3—C6—N2 | −1.0 (2) |
C7—C1—C2—C3 | 177.07 (18) | C4—C3—C6—N2 | 179.45 (17) |
C1—C2—C3—C6 | 0.5 (2) | C2—C3—C6—N4 | 179.97 (17) |
C1—C2—C3—C4 | 180.0 (2) | C4—C3—C6—N4 | 0.4 (3) |
C5—N3—C4—O1 | 171.9 (2) | C18—N1—C7—C1 | 175.24 (19) |
C8—N3—C4—O1 | −3.9 (3) | C2—C1—C7—N1 | −172.4 (2) |
C5—N3—C4—C3 | −8.8 (3) | N2—C1—C7—N1 | 3.8 (3) |
C8—N3—C4—C3 | 175.42 (19) | C6—N2—C10—C11 | −71.1 (2) |
C2—C3—C4—O1 | 4.8 (4) | C1—N2—C10—C11 | 93.0 (2) |
C6—C3—C4—O1 | −175.78 (19) | N2—C10—C11—C12 | −139.8 (2) |
C2—C3—C4—N3 | −174.5 (2) | C10—C11—C12—C14 | 0.8 (3) |
C6—C3—C4—N3 | 4.9 (3) | C10—C11—C12—C13 | −179.0 (2) |
C4—N3—C5—O2 | −173.2 (2) | C20—C15—C16—C17 | 0.5 (4) |
C8—N3—C5—O2 | 2.6 (3) | Br—C15—C16—C17 | 178.26 (18) |
C4—N3—C5—N4 | 6.9 (3) | C15—C16—C17—C18 | 0.1 (4) |
C8—N3—C5—N4 | −177.27 (19) | C16—C17—C18—C19 | −1.3 (3) |
C6—N4—C5—O2 | 179.5 (2) | C16—C17—C18—N1 | −178.1 (2) |
C9—N4—C5—O2 | 10.7 (3) | C7—N1—C18—C19 | 145.2 (2) |
C6—N4—C5—N3 | −0.7 (3) | C7—N1—C18—C17 | −38.0 (3) |
C9—N4—C5—N3 | −169.48 (19) | C17—C18—C19—C20 | 1.9 (3) |
C1—N2—C6—N4 | −179.96 (18) | N1—C18—C19—C20 | 178.96 (18) |
C10—N2—C6—N4 | −13.9 (3) | C18—C19—C20—C15 | −1.3 (3) |
C1—N2—C6—C3 | 1.1 (2) | C16—C15—C20—C19 | 0.1 (3) |
C10—N2—C6—C3 | 167.14 (17) | Br—C15—C20—C19 | −177.71 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···N1i | 0.96 | 2.59 | 3.508 (3) | 160 |
C9—H9B···O2 | 0.96 | 2.24 | 2.695 (3) | 108 |
C10—H10A···N1 | 0.97 | 2.28 | 3.015 (3) | 131 |
C20—H20···O1ii | 0.93 | 2.36 | 3.274 (3) | 167 |
Symmetry codes: (i) −x+1, −y, −z; (ii) x−1, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C20H21BrN4O2 |
Mr | 429.32 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 942.9 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 2.20 |
Crystal size (mm) | 0.25 × 0.20 × 0.18 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2001) |
Tmin, Tmax | 0.595, 0.673 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25023, 7255, 4235 |
Rint | 0.036 |
(sin θ/λ)max (Å−1) | 0.781 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.147, 1.01 |
No. of reflections | 7255 |
No. of parameters | 248 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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).
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···N1i | 0.96 | 2.59 | 3.508 (3) | 160 |
C9—H9B···O2 | 0.96 | 2.24 | 2.695 (3) | 108 |
C10—H10A···N1 | 0.97 | 2.28 | 3.015 (3) | 131 |
C20—H20···O1ii | 0.93 | 2.36 | 3.274 (3) | 167 |
Symmetry codes: (i) −x+1, −y, −z; (ii) x−1, y+1, z. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
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.