Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807035192/ci2415sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807035192/ci2415Isup2.hkl |
CCDC reference: 624428
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- R factor = 0.066
- wR factor = 0.197
- Data-to-parameter ratio = 14.4
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.50 Ratio
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 400 Ang. PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C18 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C19 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C33 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.05 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C14 = ... S PLAT793_ALERT_1_G Check the Absolute Configuration of C34 = ... S PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 18
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 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 0 ALERT type 5 Informative message, check
For synthesis, see: Robins et al. (1961). For general background, see: Meade et al. (1993); Taddei et al. (2004).
The title compound was prepared according to the literature method (Robins et al., 1961). Single crystals of the title compound were obtained by slow evaporation of a acetone-water (8:2 v/v) solution.
H atoms were placed at calculated positions (N—H = 0.86 Å and C—H = 0.93–0.98 Å) and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C,N). During the refinement, the displacement parameters of atoms C18, C19 and C33 were restrained to an approximate isotropic behaviour.
Some purine nucleosides and nucleotides have been found to act as crucial hormones, neurotransmiters or coenzymes (Taddei et al., 2004). Isosteres of purines have been isolated from natural sources and have displayed significant anti-microbial and anti-cancer activity, leading to important new medicines (Meade et al., 1993). In order to better understand the relationship between the structure and biological activity, we have synthesized the title compound and determined its crystal and molecular structure.
The asymmetric unit of the title compound contains two crystallographically independent molecules (Fig. 1). These molecules differ slightly in the orientations of the tetrahydropyran rings with respect to the purine ring system. In both the molecules the purine ring system is essentially planar and the tetrahydropyran ring adopts a chair conformation.
In the crystal structure, the two independent molecules exist as a N—H···N hydrogen-bonded dimer. Centrosymmetrically related dimers are linked together by weak C—H···O hydrogen bonds (Table 1), forming a tetramer (Fig. 2).
For synthesis, see: Robins et al. (1961). For general background, see: Meade et al. (1993); Taddei et al. (2004).
Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2005); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL.
C13H16ClN5O | Z = 4 |
Mr = 293.76 | F(000) = 616 |
Triclinic, P1 | Dx = 1.369 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.385 (4) Å | Cell parameters from 809 reflections |
b = 11.686 (4) Å | θ = 2.8–26.4° |
c = 11.692 (4) Å | µ = 0.27 mm−1 |
α = 111.380 (5)° | T = 298 K |
β = 96.954 (4)° | Prism, colourless |
γ = 94.531 (5)° | 0.15 × 0.12 × 0.10 mm |
V = 1425.0 (9) Å3 |
Bruker SMART APEX CCD area-detector diffractometer | 5203 independent reflections |
Radiation source: fine-focus sealed tube | 3410 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
φ and ω scans | θmax = 25.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→12 |
Tmin = 0.960, Tmax = 0.973 | k = −8→14 |
6270 measured reflections | l = −14→13 |
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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.197 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.1257P)2] where P = (Fo2 + 2Fc2)/3 |
5203 reflections | (Δ/σ)max = 0.001 |
361 parameters | Δρmax = 0.43 e Å−3 |
18 restraints | Δρmin = −0.39 e Å−3 |
C13H16ClN5O | γ = 94.531 (5)° |
Mr = 293.76 | V = 1425.0 (9) Å3 |
Triclinic, P1 | Z = 4 |
a = 11.385 (4) Å | Mo Kα radiation |
b = 11.686 (4) Å | µ = 0.27 mm−1 |
c = 11.692 (4) Å | T = 298 K |
α = 111.380 (5)° | 0.15 × 0.12 × 0.10 mm |
β = 96.954 (4)° |
Bruker SMART APEX CCD area-detector diffractometer | 5203 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3410 reflections with I > 2σ(I) |
Tmin = 0.960, Tmax = 0.973 | Rint = 0.052 |
6270 measured reflections |
R[F2 > 2σ(F2)] = 0.066 | 18 restraints |
wR(F2) = 0.197 | H-atom parameters constrained |
S = 0.97 | Δρmax = 0.43 e Å−3 |
5203 reflections | Δρmin = −0.39 e Å−3 |
361 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 | ||
Cl1 | 0.82375 (8) | 1.22208 (8) | 0.49371 (7) | 0.0679 (3) | |
N1 | 0.6765 (2) | 1.0223 (2) | 0.3754 (2) | 0.0446 (6) | |
C2 | 0.7559 (2) | 1.1004 (3) | 0.3569 (3) | 0.0435 (7) | |
N3 | 0.7924 (2) | 1.1026 (2) | 0.2554 (2) | 0.0457 (6) | |
C4 | 0.7344 (2) | 1.0042 (3) | 0.1565 (3) | 0.0396 (6) | |
C5 | 0.6513 (2) | 0.9123 (3) | 0.1579 (2) | 0.0410 (6) | |
C6 | 0.6234 (2) | 0.9227 (3) | 0.2749 (3) | 0.0411 (6) | |
N7 | 0.6115 (2) | 0.8259 (2) | 0.0393 (2) | 0.0504 (6) | |
C8 | 0.6701 (3) | 0.8670 (3) | −0.0301 (3) | 0.0530 (8) | |
H8 | 0.6613 | 0.8266 | −0.1160 | 0.064* | |
N9 | 0.7458 (2) | 0.9747 (2) | 0.0342 (2) | 0.0465 (6) | |
N10 | 0.5473 (2) | 0.8376 (2) | 0.2888 (2) | 0.0488 (6) | |
H10 | 0.5159 | 0.7747 | 0.2229 | 0.059* | |
C11 | 0.5135 (3) | 0.8424 (3) | 0.4043 (3) | 0.0512 (8) | |
H11 | 0.4422 | 0.8819 | 0.4258 | 0.061* | |
C12 | 0.5288 (3) | 0.7332 (3) | 0.4394 (3) | 0.0663 (10) | |
H12A | 0.5655 | 0.6664 | 0.3852 | 0.080* | |
H12B | 0.4676 | 0.7074 | 0.4793 | 0.080* | |
C13 | 0.6053 (3) | 0.8556 (3) | 0.5106 (3) | 0.0628 (9) | |
H13A | 0.5906 | 0.9033 | 0.5936 | 0.075* | |
H13B | 0.6883 | 0.8623 | 0.4995 | 0.075* | |
C14 | 0.8143 (3) | 1.0476 (3) | −0.0185 (3) | 0.0495 (7) | |
H14 | 0.8763 | 1.1050 | 0.0476 | 0.059* | |
O15 | 0.8690 (2) | 0.9658 (2) | −0.1059 (2) | 0.0680 (7) | |
C16 | 0.9436 (3) | 1.0287 (4) | −0.1627 (4) | 0.0786 (12) | |
H16A | 0.9815 | 0.9682 | −0.2230 | 0.094* | |
H16B | 1.0060 | 1.0862 | −0.0992 | 0.094* | |
C17 | 0.8755 (4) | 1.0963 (5) | −0.2247 (4) | 0.0972 (17) | |
H17A | 0.8176 | 1.0385 | −0.2933 | 0.117* | |
H17B | 0.9288 | 1.1405 | −0.2579 | 0.117* | |
C18 | 0.8136 (5) | 1.1846 (6) | −0.1353 (6) | 0.139 (2) | |
H18A | 0.7613 | 1.2225 | −0.1788 | 0.167* | |
H18B | 0.8719 | 1.2498 | −0.0741 | 0.167* | |
C19 | 0.7405 (4) | 1.1203 (5) | −0.0695 (6) | 0.122 (2) | |
H19A | 0.7101 | 1.1819 | −0.0028 | 0.147* | |
H19B | 0.6728 | 1.0662 | −0.1280 | 0.147* | |
Cl2 | 0.13063 (8) | 0.24465 (10) | −0.34039 (8) | 0.0752 (3) | |
N21 | 0.2902 (2) | 0.4357 (2) | −0.2234 (2) | 0.0481 (6) | |
C22 | 0.2118 (3) | 0.3567 (3) | −0.2043 (3) | 0.0500 (7) | |
N23 | 0.1835 (2) | 0.3502 (2) | −0.1010 (2) | 0.0501 (6) | |
C24 | 0.2502 (2) | 0.4397 (3) | −0.0029 (3) | 0.0433 (7) | |
C25 | 0.3371 (2) | 0.5292 (3) | −0.0051 (3) | 0.0420 (6) | |
C26 | 0.3549 (2) | 0.5259 (3) | −0.1223 (3) | 0.0428 (7) | |
N27 | 0.3872 (2) | 0.6087 (2) | 0.1140 (2) | 0.0471 (6) | |
C28 | 0.3303 (3) | 0.5663 (3) | 0.1848 (3) | 0.0500 (7) | |
H28 | 0.3454 | 0.6022 | 0.2712 | 0.060* | |
N29 | 0.2472 (2) | 0.4654 (2) | 0.1207 (2) | 0.0469 (6) | |
N30 | 0.4314 (2) | 0.6108 (2) | −0.1362 (2) | 0.0476 (6) | |
H30 | 0.4699 | 0.6686 | −0.0698 | 0.057* | |
C31 | 0.4541 (3) | 0.6129 (3) | −0.2525 (3) | 0.0493 (7) | |
H31 | 0.5140 | 0.5618 | −0.2903 | 0.059* | |
C32 | 0.4517 (3) | 0.7314 (3) | −0.2715 (3) | 0.0650 (9) | |
H32A | 0.4313 | 0.8018 | −0.2051 | 0.078* | |
H32B | 0.5097 | 0.7520 | −0.3176 | 0.078* | |
C33 | 0.3567 (3) | 0.6261 (4) | −0.3404 (4) | 0.0734 (11) | |
H33A | 0.2782 | 0.6322 | −0.3162 | 0.088* | |
H33B | 0.3566 | 0.5825 | −0.4286 | 0.088* | |
C34 | 0.1686 (3) | 0.4008 (3) | 0.1736 (3) | 0.0517 (8) | |
H34 | 0.1401 | 0.3167 | 0.1127 | 0.062* | |
O35 | 0.24039 (19) | 0.3944 (2) | 0.2761 (2) | 0.0628 (6) | |
C36 | 0.1765 (4) | 0.3320 (4) | 0.3394 (4) | 0.0787 (11) | |
H36A | 0.2301 | 0.3297 | 0.4095 | 0.094* | |
H36B | 0.1482 | 0.2472 | 0.2833 | 0.094* | |
C37 | 0.0730 (4) | 0.3954 (4) | 0.3849 (4) | 0.0780 (11) | |
H37A | 0.0286 | 0.3482 | 0.4225 | 0.094* | |
H37B | 0.1018 | 0.4771 | 0.4480 | 0.094* | |
C38 | −0.0070 (3) | 0.4075 (4) | 0.2807 (4) | 0.0864 (13) | |
H38A | −0.0683 | 0.4576 | 0.3134 | 0.104* | |
H38B | −0.0460 | 0.3262 | 0.2244 | 0.104* | |
C39 | 0.0643 (3) | 0.4678 (4) | 0.2101 (4) | 0.0672 (10) | |
H39A | 0.0135 | 0.4654 | 0.1362 | 0.081* | |
H39B | 0.0922 | 0.5539 | 0.2623 | 0.081* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0779 (6) | 0.0647 (6) | 0.0453 (5) | −0.0253 (5) | 0.0013 (4) | 0.0122 (4) |
N1 | 0.0468 (13) | 0.0441 (14) | 0.0402 (13) | −0.0037 (11) | 0.0079 (11) | 0.0145 (11) |
C2 | 0.0444 (15) | 0.0409 (16) | 0.0423 (16) | −0.0010 (13) | 0.0065 (13) | 0.0140 (12) |
N3 | 0.0441 (13) | 0.0449 (14) | 0.0468 (14) | −0.0022 (11) | 0.0113 (11) | 0.0163 (11) |
C4 | 0.0393 (15) | 0.0419 (16) | 0.0416 (15) | 0.0052 (12) | 0.0131 (12) | 0.0182 (12) |
C5 | 0.0414 (15) | 0.0422 (16) | 0.0398 (15) | 0.0027 (13) | 0.0086 (12) | 0.0160 (12) |
C6 | 0.0430 (15) | 0.0398 (15) | 0.0436 (15) | 0.0037 (13) | 0.0116 (12) | 0.0184 (12) |
N7 | 0.0587 (15) | 0.0512 (15) | 0.0381 (13) | −0.0066 (12) | 0.0119 (12) | 0.0148 (11) |
C8 | 0.0626 (19) | 0.0526 (19) | 0.0393 (16) | −0.0041 (15) | 0.0131 (14) | 0.0130 (14) |
N9 | 0.0509 (14) | 0.0466 (14) | 0.0434 (14) | −0.0015 (12) | 0.0164 (11) | 0.0176 (11) |
N10 | 0.0594 (15) | 0.0459 (14) | 0.0375 (13) | −0.0111 (12) | 0.0114 (11) | 0.0143 (11) |
C11 | 0.0604 (19) | 0.0507 (18) | 0.0409 (16) | −0.0036 (15) | 0.0197 (14) | 0.0141 (14) |
C12 | 0.102 (3) | 0.054 (2) | 0.0453 (18) | −0.0070 (19) | 0.0208 (18) | 0.0214 (15) |
C13 | 0.081 (2) | 0.062 (2) | 0.0415 (17) | −0.0111 (18) | 0.0127 (17) | 0.0190 (15) |
C14 | 0.0555 (18) | 0.0499 (18) | 0.0496 (17) | 0.0028 (15) | 0.0220 (14) | 0.0229 (14) |
O15 | 0.0789 (16) | 0.0623 (15) | 0.0778 (16) | 0.0137 (13) | 0.0469 (14) | 0.0324 (13) |
C16 | 0.075 (2) | 0.093 (3) | 0.089 (3) | 0.014 (2) | 0.050 (2) | 0.047 (2) |
C17 | 0.066 (2) | 0.169 (5) | 0.084 (3) | −0.010 (3) | 0.012 (2) | 0.085 (3) |
C18 | 0.144 (4) | 0.150 (5) | 0.226 (6) | 0.074 (4) | 0.107 (4) | 0.156 (5) |
C19 | 0.115 (3) | 0.147 (4) | 0.195 (5) | 0.079 (3) | 0.102 (4) | 0.134 (4) |
Cl2 | 0.0665 (6) | 0.0870 (7) | 0.0510 (5) | −0.0262 (5) | 0.0040 (4) | 0.0107 (5) |
N21 | 0.0436 (13) | 0.0539 (15) | 0.0459 (14) | −0.0004 (12) | 0.0088 (11) | 0.0187 (12) |
C22 | 0.0431 (16) | 0.0552 (19) | 0.0464 (17) | −0.0014 (14) | 0.0069 (13) | 0.0149 (14) |
N23 | 0.0454 (14) | 0.0516 (15) | 0.0511 (15) | −0.0025 (12) | 0.0108 (12) | 0.0176 (12) |
C24 | 0.0388 (15) | 0.0447 (16) | 0.0481 (17) | 0.0015 (13) | 0.0105 (13) | 0.0191 (13) |
C25 | 0.0408 (15) | 0.0419 (16) | 0.0456 (16) | 0.0036 (13) | 0.0085 (12) | 0.0192 (13) |
C26 | 0.0393 (15) | 0.0449 (16) | 0.0474 (16) | 0.0057 (13) | 0.0088 (13) | 0.0208 (13) |
N27 | 0.0523 (14) | 0.0458 (14) | 0.0442 (14) | −0.0033 (12) | 0.0082 (11) | 0.0198 (11) |
C28 | 0.0532 (18) | 0.0511 (18) | 0.0442 (16) | −0.0031 (15) | 0.0068 (14) | 0.0185 (14) |
N29 | 0.0490 (14) | 0.0487 (15) | 0.0440 (14) | −0.0011 (12) | 0.0132 (11) | 0.0184 (11) |
N30 | 0.0540 (14) | 0.0485 (14) | 0.0411 (13) | −0.0045 (12) | 0.0082 (11) | 0.0202 (11) |
C31 | 0.0487 (16) | 0.0568 (19) | 0.0449 (16) | 0.0012 (14) | 0.0132 (13) | 0.0217 (14) |
C32 | 0.072 (2) | 0.069 (2) | 0.062 (2) | −0.0064 (19) | 0.0066 (18) | 0.0386 (19) |
C33 | 0.066 (2) | 0.100 (3) | 0.063 (2) | −0.014 (2) | −0.0025 (17) | 0.049 (2) |
C34 | 0.0553 (18) | 0.0491 (18) | 0.0484 (18) | −0.0055 (15) | 0.0167 (14) | 0.0157 (14) |
O35 | 0.0607 (13) | 0.0759 (17) | 0.0714 (16) | 0.0094 (12) | 0.0236 (12) | 0.0466 (13) |
C36 | 0.100 (3) | 0.079 (3) | 0.078 (3) | 0.005 (2) | 0.036 (2) | 0.048 (2) |
C37 | 0.089 (3) | 0.079 (3) | 0.070 (2) | −0.003 (2) | 0.041 (2) | 0.026 (2) |
C38 | 0.063 (2) | 0.100 (3) | 0.094 (3) | −0.003 (2) | 0.037 (2) | 0.029 (3) |
C39 | 0.0493 (19) | 0.077 (2) | 0.080 (3) | 0.0068 (18) | 0.0188 (18) | 0.033 (2) |
Cl1—C2 | 1.746 (3) | Cl2—C22 | 1.742 (3) |
N1—C2 | 1.326 (3) | N21—C22 | 1.329 (4) |
N1—C6 | 1.349 (3) | N21—C26 | 1.345 (4) |
C2—N3 | 1.312 (3) | C22—N23 | 1.312 (4) |
N3—C4 | 1.349 (3) | N23—C24 | 1.332 (4) |
C4—N9 | 1.368 (3) | C24—N29 | 1.370 (4) |
C4—C5 | 1.380 (4) | C24—C25 | 1.391 (4) |
C5—N7 | 1.380 (4) | C25—N27 | 1.382 (4) |
C5—C6 | 1.405 (4) | C25—C26 | 1.396 (4) |
C6—N10 | 1.335 (3) | C26—N30 | 1.336 (3) |
N7—C8 | 1.303 (4) | N27—C28 | 1.315 (3) |
C8—N9 | 1.368 (4) | C28—N29 | 1.362 (4) |
C8—H8 | 0.93 | C28—H28 | 0.93 |
N9—C14 | 1.453 (3) | N29—C34 | 1.457 (3) |
N10—C11 | 1.431 (3) | N30—C31 | 1.424 (4) |
N10—H10 | 0.86 | N30—H30 | 0.86 |
C11—C13 | 1.477 (5) | C31—C33 | 1.475 (5) |
C11—C12 | 1.492 (5) | C31—C32 | 1.482 (4) |
C11—H11 | 0.98 | C31—H31 | 0.98 |
C12—C13 | 1.502 (5) | C32—C33 | 1.479 (5) |
C12—H12A | 0.97 | C32—H32A | 0.97 |
C12—H12B | 0.97 | C32—H32B | 0.97 |
C13—H13A | 0.97 | C33—H33A | 0.97 |
C13—H13B | 0.97 | C33—H33B | 0.97 |
C14—O15 | 1.372 (4) | C34—O35 | 1.395 (4) |
C14—C19 | 1.464 (5) | C34—C39 | 1.494 (4) |
C14—H14 | 0.98 | C34—H34 | 0.98 |
O15—C16 | 1.449 (4) | O35—C36 | 1.431 (4) |
C16—C17 | 1.459 (6) | C36—C37 | 1.491 (5) |
C16—H16A | 0.97 | C36—H36A | 0.97 |
C16—H16B | 0.97 | C36—H36B | 0.97 |
C17—C18 | 1.469 (7) | C37—C38 | 1.487 (6) |
C17—H17A | 0.97 | C37—H37A | 0.97 |
C17—H17B | 0.97 | C37—H37B | 0.97 |
C18—C19 | 1.526 (5) | C38—C39 | 1.528 (5) |
C18—H18A | 0.97 | C38—H38A | 0.97 |
C18—H18B | 0.97 | C38—H38B | 0.97 |
C19—H19A | 0.97 | C39—H39A | 0.97 |
C19—H19B | 0.97 | C39—H39B | 0.97 |
C2—N1—C6 | 117.1 (2) | C22—N21—C26 | 117.3 (2) |
N3—C2—N1 | 131.9 (3) | N23—C22—N21 | 131.2 (3) |
N3—C2—Cl1 | 114.7 (2) | N23—C22—Cl2 | 114.8 (2) |
N1—C2—Cl1 | 113.4 (2) | N21—C22—Cl2 | 114.0 (2) |
C2—N3—C4 | 109.3 (2) | C22—N23—C24 | 110.0 (2) |
N3—C4—N9 | 127.3 (2) | N23—C24—N29 | 128.1 (3) |
N3—C4—C5 | 127.0 (2) | N23—C24—C25 | 126.7 (3) |
N9—C4—C5 | 105.7 (2) | N29—C24—C25 | 105.2 (2) |
N7—C5—C4 | 111.0 (2) | N27—C25—C24 | 111.2 (2) |
N7—C5—C6 | 132.5 (3) | N27—C25—C26 | 132.3 (3) |
C4—C5—C6 | 116.6 (3) | C24—C25—C26 | 116.5 (3) |
N10—C6—N1 | 119.8 (2) | N30—C26—N21 | 119.7 (3) |
N10—C6—C5 | 122.2 (3) | N30—C26—C25 | 122.0 (3) |
N1—C6—C5 | 118.1 (2) | N21—C26—C25 | 118.2 (3) |
C8—N7—C5 | 103.5 (2) | C28—N27—C25 | 103.2 (2) |
N7—C8—N9 | 114.3 (3) | N27—C28—N29 | 114.3 (3) |
N7—C8—H8 | 122.8 | N27—C28—H28 | 122.9 |
N9—C8—H8 | 122.8 | N29—C28—H28 | 122.9 |
C4—N9—C8 | 105.5 (2) | C28—N29—C24 | 106.2 (2) |
C4—N9—C14 | 127.6 (2) | C28—N29—C34 | 126.6 (2) |
C8—N9—C14 | 126.7 (2) | C24—N29—C34 | 127.2 (2) |
C6—N10—C11 | 125.4 (2) | C26—N30—C31 | 125.0 (3) |
C6—N10—H10 | 117.3 | C26—N30—H30 | 117.5 |
C11—N10—H10 | 117.3 | C31—N30—H30 | 117.5 |
N10—C11—C13 | 120.4 (3) | N30—C31—C33 | 120.0 (3) |
N10—C11—C12 | 117.5 (3) | N30—C31—C32 | 118.0 (3) |
C13—C11—C12 | 60.8 (2) | C33—C31—C32 | 60.0 (2) |
N10—C11—H11 | 115.6 | N30—C31—H31 | 115.8 |
C13—C11—H11 | 115.6 | C33—C31—H31 | 115.8 |
C12—C11—H11 | 115.6 | C32—C31—H31 | 115.8 |
C11—C12—C13 | 59.1 (2) | C33—C32—C31 | 59.7 (2) |
C11—C12—H12A | 117.9 | C33—C32—H32A | 117.8 |
C13—C12—H12A | 117.9 | C31—C32—H32A | 117.8 |
C11—C12—H12B | 117.9 | C33—C32—H32B | 117.8 |
C13—C12—H12B | 117.9 | C31—C32—H32B | 117.8 |
H12A—C12—H12B | 115.0 | H32A—C32—H32B | 114.9 |
C11—C13—C12 | 60.1 (2) | C31—C33—C32 | 60.2 (2) |
C11—C13—H13A | 117.8 | C31—C33—H33A | 117.7 |
C12—C13—H13A | 117.8 | C32—C33—H33A | 117.7 |
C11—C13—H13B | 117.8 | C31—C33—H33B | 117.7 |
C12—C13—H13B | 117.8 | C32—C33—H33B | 117.7 |
H13A—C13—H13B | 114.9 | H33A—C33—H33B | 114.9 |
O15—C14—N9 | 106.4 (2) | O35—C34—N29 | 105.0 (2) |
O15—C14—C19 | 112.9 (3) | O35—C34—C39 | 111.9 (3) |
N9—C14—C19 | 112.4 (3) | N29—C34—C39 | 111.4 (3) |
O15—C14—H14 | 108.3 | O35—C34—H34 | 109.5 |
N9—C14—H14 | 108.3 | N29—C34—H34 | 109.5 |
C19—C14—H14 | 108.3 | C39—C34—H34 | 109.5 |
C14—O15—C16 | 111.5 (3) | C34—O35—C36 | 112.4 (3) |
O15—C16—C17 | 112.1 (3) | O35—C36—C37 | 111.4 (3) |
O15—C16—H16A | 109.2 | O35—C36—H36A | 109.3 |
C17—C16—H16A | 109.2 | C37—C36—H36A | 109.3 |
O15—C16—H16B | 109.2 | O35—C36—H36B | 109.3 |
C17—C16—H16B | 109.2 | C37—C36—H36B | 109.3 |
H16A—C16—H16B | 107.9 | H36A—C36—H36B | 108.0 |
C16—C17—C18 | 109.6 (4) | C38—C37—C36 | 110.7 (3) |
C16—C17—H17A | 109.7 | C38—C37—H37A | 109.5 |
C18—C17—H17A | 109.7 | C36—C37—H37A | 109.5 |
C16—C17—H17B | 109.7 | C38—C37—H37B | 109.5 |
C18—C17—H17B | 109.7 | C36—C37—H37B | 109.5 |
H17A—C17—H17B | 108.2 | H37A—C37—H37B | 108.1 |
C17—C18—C19 | 111.1 (4) | C37—C38—C39 | 110.4 (3) |
C17—C18—H18A | 109.4 | C37—C38—H38A | 109.6 |
C19—C18—H18A | 109.4 | C39—C38—H38A | 109.6 |
C17—C18—H18B | 109.4 | C37—C38—H38B | 109.6 |
C19—C18—H18B | 109.4 | C39—C38—H38B | 109.6 |
H18A—C18—H18B | 108.0 | H38A—C38—H38B | 108.1 |
C14—C19—C18 | 110.3 (3) | C34—C39—C38 | 110.1 (3) |
C14—C19—H19A | 109.6 | C34—C39—H39A | 109.6 |
C18—C19—H19A | 109.6 | C38—C39—H39A | 109.6 |
C14—C19—H19B | 109.6 | C34—C39—H39B | 109.6 |
C18—C19—H19B | 109.6 | C38—C39—H39B | 109.6 |
H19A—C19—H19B | 108.1 | H39A—C39—H39B | 108.2 |
C6—N1—C2—N3 | 2.4 (5) | C26—N21—C22—N23 | 0.7 (5) |
C6—N1—C2—Cl1 | −177.4 (2) | C26—N21—C22—Cl2 | 179.1 (2) |
N1—C2—N3—C4 | −0.1 (4) | N21—C22—N23—C24 | −1.4 (5) |
Cl1—C2—N3—C4 | 179.67 (19) | Cl2—C22—N23—C24 | −179.8 (2) |
C2—N3—C4—N9 | 178.8 (3) | C22—N23—C24—N29 | 179.2 (3) |
C2—N3—C4—C5 | −1.4 (4) | C22—N23—C24—C25 | 0.4 (4) |
N3—C4—C5—N7 | −179.5 (3) | N23—C24—C25—N27 | 179.0 (3) |
N9—C4—C5—N7 | 0.4 (3) | N29—C24—C25—N27 | 0.0 (3) |
N3—C4—C5—C6 | 0.5 (4) | N23—C24—C25—C26 | 1.1 (4) |
N9—C4—C5—C6 | −179.6 (2) | N29—C24—C25—C26 | −177.9 (2) |
C2—N1—C6—N10 | 176.6 (3) | C22—N21—C26—N30 | −177.2 (3) |
C2—N1—C6—C5 | −3.2 (4) | C22—N21—C26—C25 | 1.1 (4) |
N7—C5—C6—N10 | 2.1 (5) | N27—C25—C26—N30 | −0.9 (5) |
C4—C5—C6—N10 | −177.9 (3) | C24—C25—C26—N30 | 176.4 (2) |
N7—C5—C6—N1 | −178.1 (3) | N27—C25—C26—N21 | −179.2 (3) |
C4—C5—C6—N1 | 1.9 (4) | C24—C25—C26—N21 | −1.8 (4) |
C4—C5—N7—C8 | −0.2 (3) | C24—C25—N27—C28 | 0.0 (3) |
C6—C5—N7—C8 | 179.9 (3) | C26—C25—N27—C28 | 177.4 (3) |
C5—N7—C8—N9 | −0.1 (3) | C25—N27—C28—N29 | 0.0 (3) |
N3—C4—N9—C8 | 179.4 (3) | N27—C28—N29—C24 | 0.0 (3) |
C5—C4—N9—C8 | −0.4 (3) | N27—C28—N29—C34 | −178.2 (3) |
N3—C4—N9—C14 | −6.0 (5) | N23—C24—N29—C28 | −178.9 (3) |
C5—C4—N9—C14 | 174.1 (3) | C25—C24—N29—C28 | 0.0 (3) |
N7—C8—N9—C4 | 0.4 (4) | N23—C24—N29—C34 | −0.8 (5) |
N7—C8—N9—C14 | −174.2 (3) | C25—C24—N29—C34 | 178.2 (3) |
N1—C6—N10—C11 | 0.9 (4) | N21—C26—N30—C31 | −1.9 (4) |
C5—C6—N10—C11 | −179.3 (3) | C25—C26—N30—C31 | 179.9 (3) |
C6—N10—C11—C13 | −55.2 (4) | C26—N30—C31—C33 | 61.6 (4) |
C6—N10—C11—C12 | −125.8 (3) | C26—N30—C31—C32 | 131.3 (3) |
N10—C11—C12—C13 | 111.3 (3) | N30—C31—C32—C33 | −110.3 (3) |
N10—C11—C13—C12 | −106.6 (3) | N30—C31—C33—C32 | 107.1 (3) |
C4—N9—C14—O15 | 138.7 (3) | C28—N29—C34—O35 | −41.8 (4) |
C8—N9—C14—O15 | −47.9 (4) | C24—N29—C34—O35 | 140.4 (3) |
C4—N9—C14—C19 | −97.2 (4) | C28—N29—C34—C39 | 79.5 (4) |
C8—N9—C14—C19 | 76.2 (4) | C24—N29—C34—C39 | −98.3 (4) |
N9—C14—O15—C16 | −178.2 (3) | N29—C34—O35—C36 | −179.6 (3) |
C19—C14—O15—C16 | 58.1 (4) | C39—C34—O35—C36 | 59.4 (4) |
C14—O15—C16—C17 | −59.6 (5) | C34—O35—C36—C37 | −59.2 (4) |
O15—C16—C17—C18 | 56.5 (5) | O35—C36—C37—C38 | 55.5 (5) |
C16—C17—C18—C19 | −52.5 (6) | C36—C37—C38—C39 | −52.3 (5) |
O15—C14—C19—C18 | −53.9 (6) | O35—C34—C39—C38 | −55.3 (4) |
N9—C14—C19—C18 | −174.2 (4) | N29—C34—C39—C38 | −172.5 (3) |
C17—C18—C19—C14 | 50.9 (7) | C37—C38—C39—C34 | 51.9 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N10—H10···N27 | 0.86 | 2.20 | 2.998 (3) | 155 |
N30—H30···N7 | 0.86 | 2.22 | 3.023 (4) | 155 |
C36—H36B···O15i | 0.97 | 2.57 | 3.504 (5) | 162 |
Symmetry code: (i) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C13H16ClN5O |
Mr | 293.76 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 11.385 (4), 11.686 (4), 11.692 (4) |
α, β, γ (°) | 111.380 (5), 96.954 (4), 94.531 (5) |
V (Å3) | 1425.0 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.27 |
Crystal size (mm) | 0.15 × 0.12 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.960, 0.973 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6270, 5203, 3410 |
Rint | 0.052 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.197, 0.97 |
No. of reflections | 5203 |
No. of parameters | 361 |
No. of restraints | 18 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.43, −0.39 |
Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SAINT, SHELXTL (Bruker, 2005), SHELXTL, PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N10—H10···N27 | 0.86 | 2.20 | 2.998 (3) | 155 |
N30—H30···N7 | 0.86 | 2.22 | 3.023 (4) | 155 |
C36—H36B···O15i | 0.97 | 2.57 | 3.504 (5) | 162 |
Symmetry code: (i) −x+1, −y+1, −z. |
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Some purine nucleosides and nucleotides have been found to act as crucial hormones, neurotransmiters or coenzymes (Taddei et al., 2004). Isosteres of purines have been isolated from natural sources and have displayed significant anti-microbial and anti-cancer activity, leading to important new medicines (Meade et al., 1993). In order to better understand the relationship between the structure and biological activity, we have synthesized the title compound and determined its crystal and molecular structure.
The asymmetric unit of the title compound contains two crystallographically independent molecules (Fig. 1). These molecules differ slightly in the orientations of the tetrahydropyran rings with respect to the purine ring system. In both the molecules the purine ring system is essentially planar and the tetrahydropyran ring adopts a chair conformation.
In the crystal structure, the two independent molecules exist as a N—H···N hydrogen-bonded dimer. Centrosymmetrically related dimers are linked together by weak C—H···O hydrogen bonds (Table 1), forming a tetramer (Fig. 2).