Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The title compound, C13H16ClN5O, crystallizes with two mol­ecules in the asymmetric unit, which differ in the orientation of the tetra­hydro­pyran ring with respect to the purine ring system. In both mol­ecules, the purine ring system is essentially planar and the tetra­hydro­pyran ring adopts a chair conformation. The two independent mol­ecules exist as an N—H...N hydrogen-bonded dimer. Centrosymmetrically related dimers are linked together by weak C—H...O hydrogen bonds, forming a tetra­mer.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807035192/ci2415sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807035192/ci2415Isup2.hkl
Contains datablock I

CCDC reference: 624428

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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

Comment top

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).

Related literature top

For synthesis, see: Robins et al. (1961). For general background, see: Meade et al. (1993); Taddei et al. (2004).

Experimental top

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.

Refinement top

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.

Structure description top

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).

Computing details top

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.

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound, showing two independent molecules. Displacement ellipsoids are drawn at the 30% probability level. Dashed lines indicate hydrogen bonds.
[Figure 2] Fig. 2. The packing diagram of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.
2-Chloro-N-cyclopropyl-9-(3,4,5,6-tetrahydro-2H-pyran-2-yl)- 9H-purin-6-amine top
Crystal data top
C13H16ClN5OZ = 4
Mr = 293.76F(000) = 616
Triclinic, P1Dx = 1.369 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.385 (4) ÅCell parameters from 809 reflections
b = 11.686 (4) Åθ = 2.8–26.4°
c = 11.692 (4) ŵ = 0.27 mm1
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
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
5203 independent reflections
Radiation source: fine-focus sealed tube3410 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
φ and ω scansθmax = 25.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1312
Tmin = 0.960, Tmax = 0.973k = 814
6270 measured reflectionsl = 1413
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)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.197H-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 parametersΔρmax = 0.43 e Å3
18 restraintsΔρmin = 0.39 e Å3
Crystal data top
C13H16ClN5Oγ = 94.531 (5)°
Mr = 293.76V = 1425.0 (9) Å3
Triclinic, P1Z = 4
a = 11.385 (4) ÅMo Kα radiation
b = 11.686 (4) ŵ = 0.27 mm1
c = 11.692 (4) ÅT = 298 K
α = 111.380 (5)°0.15 × 0.12 × 0.10 mm
β = 96.954 (4)°
Data collection top
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 = 0.973Rint = 0.052
6270 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06618 restraints
wR(F2) = 0.197H-atom parameters constrained
S = 0.97Δρmax = 0.43 e Å3
5203 reflectionsΔρmin = 0.39 e Å3
361 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
Cl10.82375 (8)1.22208 (8)0.49371 (7)0.0679 (3)
N10.6765 (2)1.0223 (2)0.3754 (2)0.0446 (6)
C20.7559 (2)1.1004 (3)0.3569 (3)0.0435 (7)
N30.7924 (2)1.1026 (2)0.2554 (2)0.0457 (6)
C40.7344 (2)1.0042 (3)0.1565 (3)0.0396 (6)
C50.6513 (2)0.9123 (3)0.1579 (2)0.0410 (6)
C60.6234 (2)0.9227 (3)0.2749 (3)0.0411 (6)
N70.6115 (2)0.8259 (2)0.0393 (2)0.0504 (6)
C80.6701 (3)0.8670 (3)0.0301 (3)0.0530 (8)
H80.66130.82660.11600.064*
N90.7458 (2)0.9747 (2)0.0342 (2)0.0465 (6)
N100.5473 (2)0.8376 (2)0.2888 (2)0.0488 (6)
H100.51590.77470.22290.059*
C110.5135 (3)0.8424 (3)0.4043 (3)0.0512 (8)
H110.44220.88190.42580.061*
C120.5288 (3)0.7332 (3)0.4394 (3)0.0663 (10)
H12A0.56550.66640.38520.080*
H12B0.46760.70740.47930.080*
C130.6053 (3)0.8556 (3)0.5106 (3)0.0628 (9)
H13A0.59060.90330.59360.075*
H13B0.68830.86230.49950.075*
C140.8143 (3)1.0476 (3)0.0185 (3)0.0495 (7)
H140.87631.10500.04760.059*
O150.8690 (2)0.9658 (2)0.1059 (2)0.0680 (7)
C160.9436 (3)1.0287 (4)0.1627 (4)0.0786 (12)
H16A0.98150.96820.22300.094*
H16B1.00601.08620.09920.094*
C170.8755 (4)1.0963 (5)0.2247 (4)0.0972 (17)
H17A0.81761.03850.29330.117*
H17B0.92881.14050.25790.117*
C180.8136 (5)1.1846 (6)0.1353 (6)0.139 (2)
H18A0.76131.22250.17880.167*
H18B0.87191.24980.07410.167*
C190.7405 (4)1.1203 (5)0.0695 (6)0.122 (2)
H19A0.71011.18190.00280.147*
H19B0.67281.06620.12800.147*
Cl20.13063 (8)0.24465 (10)0.34039 (8)0.0752 (3)
N210.2902 (2)0.4357 (2)0.2234 (2)0.0481 (6)
C220.2118 (3)0.3567 (3)0.2043 (3)0.0500 (7)
N230.1835 (2)0.3502 (2)0.1010 (2)0.0501 (6)
C240.2502 (2)0.4397 (3)0.0029 (3)0.0433 (7)
C250.3371 (2)0.5292 (3)0.0051 (3)0.0420 (6)
C260.3549 (2)0.5259 (3)0.1223 (3)0.0428 (7)
N270.3872 (2)0.6087 (2)0.1140 (2)0.0471 (6)
C280.3303 (3)0.5663 (3)0.1848 (3)0.0500 (7)
H280.34540.60220.27120.060*
N290.2472 (2)0.4654 (2)0.1207 (2)0.0469 (6)
N300.4314 (2)0.6108 (2)0.1362 (2)0.0476 (6)
H300.46990.66860.06980.057*
C310.4541 (3)0.6129 (3)0.2525 (3)0.0493 (7)
H310.51400.56180.29030.059*
C320.4517 (3)0.7314 (3)0.2715 (3)0.0650 (9)
H32A0.43130.80180.20510.078*
H32B0.50970.75200.31760.078*
C330.3567 (3)0.6261 (4)0.3404 (4)0.0734 (11)
H33A0.27820.63220.31620.088*
H33B0.35660.58250.42860.088*
C340.1686 (3)0.4008 (3)0.1736 (3)0.0517 (8)
H340.14010.31670.11270.062*
O350.24039 (19)0.3944 (2)0.2761 (2)0.0628 (6)
C360.1765 (4)0.3320 (4)0.3394 (4)0.0787 (11)
H36A0.23010.32970.40950.094*
H36B0.14820.24720.28330.094*
C370.0730 (4)0.3954 (4)0.3849 (4)0.0780 (11)
H37A0.02860.34820.42250.094*
H37B0.10180.47710.44800.094*
C380.0070 (3)0.4075 (4)0.2807 (4)0.0864 (13)
H38A0.06830.45760.31340.104*
H38B0.04600.32620.22440.104*
C390.0643 (3)0.4678 (4)0.2101 (4)0.0672 (10)
H39A0.01350.46540.13620.081*
H39B0.09220.55390.26230.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0779 (6)0.0647 (6)0.0453 (5)0.0253 (5)0.0013 (4)0.0122 (4)
N10.0468 (13)0.0441 (14)0.0402 (13)0.0037 (11)0.0079 (11)0.0145 (11)
C20.0444 (15)0.0409 (16)0.0423 (16)0.0010 (13)0.0065 (13)0.0140 (12)
N30.0441 (13)0.0449 (14)0.0468 (14)0.0022 (11)0.0113 (11)0.0163 (11)
C40.0393 (15)0.0419 (16)0.0416 (15)0.0052 (12)0.0131 (12)0.0182 (12)
C50.0414 (15)0.0422 (16)0.0398 (15)0.0027 (13)0.0086 (12)0.0160 (12)
C60.0430 (15)0.0398 (15)0.0436 (15)0.0037 (13)0.0116 (12)0.0184 (12)
N70.0587 (15)0.0512 (15)0.0381 (13)0.0066 (12)0.0119 (12)0.0148 (11)
C80.0626 (19)0.0526 (19)0.0393 (16)0.0041 (15)0.0131 (14)0.0130 (14)
N90.0509 (14)0.0466 (14)0.0434 (14)0.0015 (12)0.0164 (11)0.0176 (11)
N100.0594 (15)0.0459 (14)0.0375 (13)0.0111 (12)0.0114 (11)0.0143 (11)
C110.0604 (19)0.0507 (18)0.0409 (16)0.0036 (15)0.0197 (14)0.0141 (14)
C120.102 (3)0.054 (2)0.0453 (18)0.0070 (19)0.0208 (18)0.0214 (15)
C130.081 (2)0.062 (2)0.0415 (17)0.0111 (18)0.0127 (17)0.0190 (15)
C140.0555 (18)0.0499 (18)0.0496 (17)0.0028 (15)0.0220 (14)0.0229 (14)
O150.0789 (16)0.0623 (15)0.0778 (16)0.0137 (13)0.0469 (14)0.0324 (13)
C160.075 (2)0.093 (3)0.089 (3)0.014 (2)0.050 (2)0.047 (2)
C170.066 (2)0.169 (5)0.084 (3)0.010 (3)0.012 (2)0.085 (3)
C180.144 (4)0.150 (5)0.226 (6)0.074 (4)0.107 (4)0.156 (5)
C190.115 (3)0.147 (4)0.195 (5)0.079 (3)0.102 (4)0.134 (4)
Cl20.0665 (6)0.0870 (7)0.0510 (5)0.0262 (5)0.0040 (4)0.0107 (5)
N210.0436 (13)0.0539 (15)0.0459 (14)0.0004 (12)0.0088 (11)0.0187 (12)
C220.0431 (16)0.0552 (19)0.0464 (17)0.0014 (14)0.0069 (13)0.0149 (14)
N230.0454 (14)0.0516 (15)0.0511 (15)0.0025 (12)0.0108 (12)0.0176 (12)
C240.0388 (15)0.0447 (16)0.0481 (17)0.0015 (13)0.0105 (13)0.0191 (13)
C250.0408 (15)0.0419 (16)0.0456 (16)0.0036 (13)0.0085 (12)0.0192 (13)
C260.0393 (15)0.0449 (16)0.0474 (16)0.0057 (13)0.0088 (13)0.0208 (13)
N270.0523 (14)0.0458 (14)0.0442 (14)0.0033 (12)0.0082 (11)0.0198 (11)
C280.0532 (18)0.0511 (18)0.0442 (16)0.0031 (15)0.0068 (14)0.0185 (14)
N290.0490 (14)0.0487 (15)0.0440 (14)0.0011 (12)0.0132 (11)0.0184 (11)
N300.0540 (14)0.0485 (14)0.0411 (13)0.0045 (12)0.0082 (11)0.0202 (11)
C310.0487 (16)0.0568 (19)0.0449 (16)0.0012 (14)0.0132 (13)0.0217 (14)
C320.072 (2)0.069 (2)0.062 (2)0.0064 (19)0.0066 (18)0.0386 (19)
C330.066 (2)0.100 (3)0.063 (2)0.014 (2)0.0025 (17)0.049 (2)
C340.0553 (18)0.0491 (18)0.0484 (18)0.0055 (15)0.0167 (14)0.0157 (14)
O350.0607 (13)0.0759 (17)0.0714 (16)0.0094 (12)0.0236 (12)0.0466 (13)
C360.100 (3)0.079 (3)0.078 (3)0.005 (2)0.036 (2)0.048 (2)
C370.089 (3)0.079 (3)0.070 (2)0.003 (2)0.041 (2)0.026 (2)
C380.063 (2)0.100 (3)0.094 (3)0.003 (2)0.037 (2)0.029 (3)
C390.0493 (19)0.077 (2)0.080 (3)0.0068 (18)0.0188 (18)0.033 (2)
Geometric parameters (Å, º) top
Cl1—C21.746 (3)Cl2—C221.742 (3)
N1—C21.326 (3)N21—C221.329 (4)
N1—C61.349 (3)N21—C261.345 (4)
C2—N31.312 (3)C22—N231.312 (4)
N3—C41.349 (3)N23—C241.332 (4)
C4—N91.368 (3)C24—N291.370 (4)
C4—C51.380 (4)C24—C251.391 (4)
C5—N71.380 (4)C25—N271.382 (4)
C5—C61.405 (4)C25—C261.396 (4)
C6—N101.335 (3)C26—N301.336 (3)
N7—C81.303 (4)N27—C281.315 (3)
C8—N91.368 (4)C28—N291.362 (4)
C8—H80.93C28—H280.93
N9—C141.453 (3)N29—C341.457 (3)
N10—C111.431 (3)N30—C311.424 (4)
N10—H100.86N30—H300.86
C11—C131.477 (5)C31—C331.475 (5)
C11—C121.492 (5)C31—C321.482 (4)
C11—H110.98C31—H310.98
C12—C131.502 (5)C32—C331.479 (5)
C12—H12A0.97C32—H32A0.97
C12—H12B0.97C32—H32B0.97
C13—H13A0.97C33—H33A0.97
C13—H13B0.97C33—H33B0.97
C14—O151.372 (4)C34—O351.395 (4)
C14—C191.464 (5)C34—C391.494 (4)
C14—H140.98C34—H340.98
O15—C161.449 (4)O35—C361.431 (4)
C16—C171.459 (6)C36—C371.491 (5)
C16—H16A0.97C36—H36A0.97
C16—H16B0.97C36—H36B0.97
C17—C181.469 (7)C37—C381.487 (6)
C17—H17A0.97C37—H37A0.97
C17—H17B0.97C37—H37B0.97
C18—C191.526 (5)C38—C391.528 (5)
C18—H18A0.97C38—H38A0.97
C18—H18B0.97C38—H38B0.97
C19—H19A0.97C39—H39A0.97
C19—H19B0.97C39—H39B0.97
C2—N1—C6117.1 (2)C22—N21—C26117.3 (2)
N3—C2—N1131.9 (3)N23—C22—N21131.2 (3)
N3—C2—Cl1114.7 (2)N23—C22—Cl2114.8 (2)
N1—C2—Cl1113.4 (2)N21—C22—Cl2114.0 (2)
C2—N3—C4109.3 (2)C22—N23—C24110.0 (2)
N3—C4—N9127.3 (2)N23—C24—N29128.1 (3)
N3—C4—C5127.0 (2)N23—C24—C25126.7 (3)
N9—C4—C5105.7 (2)N29—C24—C25105.2 (2)
N7—C5—C4111.0 (2)N27—C25—C24111.2 (2)
N7—C5—C6132.5 (3)N27—C25—C26132.3 (3)
C4—C5—C6116.6 (3)C24—C25—C26116.5 (3)
N10—C6—N1119.8 (2)N30—C26—N21119.7 (3)
N10—C6—C5122.2 (3)N30—C26—C25122.0 (3)
N1—C6—C5118.1 (2)N21—C26—C25118.2 (3)
C8—N7—C5103.5 (2)C28—N27—C25103.2 (2)
N7—C8—N9114.3 (3)N27—C28—N29114.3 (3)
N7—C8—H8122.8N27—C28—H28122.9
N9—C8—H8122.8N29—C28—H28122.9
C4—N9—C8105.5 (2)C28—N29—C24106.2 (2)
C4—N9—C14127.6 (2)C28—N29—C34126.6 (2)
C8—N9—C14126.7 (2)C24—N29—C34127.2 (2)
C6—N10—C11125.4 (2)C26—N30—C31125.0 (3)
C6—N10—H10117.3C26—N30—H30117.5
C11—N10—H10117.3C31—N30—H30117.5
N10—C11—C13120.4 (3)N30—C31—C33120.0 (3)
N10—C11—C12117.5 (3)N30—C31—C32118.0 (3)
C13—C11—C1260.8 (2)C33—C31—C3260.0 (2)
N10—C11—H11115.6N30—C31—H31115.8
C13—C11—H11115.6C33—C31—H31115.8
C12—C11—H11115.6C32—C31—H31115.8
C11—C12—C1359.1 (2)C33—C32—C3159.7 (2)
C11—C12—H12A117.9C33—C32—H32A117.8
C13—C12—H12A117.9C31—C32—H32A117.8
C11—C12—H12B117.9C33—C32—H32B117.8
C13—C12—H12B117.9C31—C32—H32B117.8
H12A—C12—H12B115.0H32A—C32—H32B114.9
C11—C13—C1260.1 (2)C31—C33—C3260.2 (2)
C11—C13—H13A117.8C31—C33—H33A117.7
C12—C13—H13A117.8C32—C33—H33A117.7
C11—C13—H13B117.8C31—C33—H33B117.7
C12—C13—H13B117.8C32—C33—H33B117.7
H13A—C13—H13B114.9H33A—C33—H33B114.9
O15—C14—N9106.4 (2)O35—C34—N29105.0 (2)
O15—C14—C19112.9 (3)O35—C34—C39111.9 (3)
N9—C14—C19112.4 (3)N29—C34—C39111.4 (3)
O15—C14—H14108.3O35—C34—H34109.5
N9—C14—H14108.3N29—C34—H34109.5
C19—C14—H14108.3C39—C34—H34109.5
C14—O15—C16111.5 (3)C34—O35—C36112.4 (3)
O15—C16—C17112.1 (3)O35—C36—C37111.4 (3)
O15—C16—H16A109.2O35—C36—H36A109.3
C17—C16—H16A109.2C37—C36—H36A109.3
O15—C16—H16B109.2O35—C36—H36B109.3
C17—C16—H16B109.2C37—C36—H36B109.3
H16A—C16—H16B107.9H36A—C36—H36B108.0
C16—C17—C18109.6 (4)C38—C37—C36110.7 (3)
C16—C17—H17A109.7C38—C37—H37A109.5
C18—C17—H17A109.7C36—C37—H37A109.5
C16—C17—H17B109.7C38—C37—H37B109.5
C18—C17—H17B109.7C36—C37—H37B109.5
H17A—C17—H17B108.2H37A—C37—H37B108.1
C17—C18—C19111.1 (4)C37—C38—C39110.4 (3)
C17—C18—H18A109.4C37—C38—H38A109.6
C19—C18—H18A109.4C39—C38—H38A109.6
C17—C18—H18B109.4C37—C38—H38B109.6
C19—C18—H18B109.4C39—C38—H38B109.6
H18A—C18—H18B108.0H38A—C38—H38B108.1
C14—C19—C18110.3 (3)C34—C39—C38110.1 (3)
C14—C19—H19A109.6C34—C39—H39A109.6
C18—C19—H19A109.6C38—C39—H39A109.6
C14—C19—H19B109.6C34—C39—H39B109.6
C18—C19—H19B109.6C38—C39—H39B109.6
H19A—C19—H19B108.1H39A—C39—H39B108.2
C6—N1—C2—N32.4 (5)C26—N21—C22—N230.7 (5)
C6—N1—C2—Cl1177.4 (2)C26—N21—C22—Cl2179.1 (2)
N1—C2—N3—C40.1 (4)N21—C22—N23—C241.4 (5)
Cl1—C2—N3—C4179.67 (19)Cl2—C22—N23—C24179.8 (2)
C2—N3—C4—N9178.8 (3)C22—N23—C24—N29179.2 (3)
C2—N3—C4—C51.4 (4)C22—N23—C24—C250.4 (4)
N3—C4—C5—N7179.5 (3)N23—C24—C25—N27179.0 (3)
N9—C4—C5—N70.4 (3)N29—C24—C25—N270.0 (3)
N3—C4—C5—C60.5 (4)N23—C24—C25—C261.1 (4)
N9—C4—C5—C6179.6 (2)N29—C24—C25—C26177.9 (2)
C2—N1—C6—N10176.6 (3)C22—N21—C26—N30177.2 (3)
C2—N1—C6—C53.2 (4)C22—N21—C26—C251.1 (4)
N7—C5—C6—N102.1 (5)N27—C25—C26—N300.9 (5)
C4—C5—C6—N10177.9 (3)C24—C25—C26—N30176.4 (2)
N7—C5—C6—N1178.1 (3)N27—C25—C26—N21179.2 (3)
C4—C5—C6—N11.9 (4)C24—C25—C26—N211.8 (4)
C4—C5—N7—C80.2 (3)C24—C25—N27—C280.0 (3)
C6—C5—N7—C8179.9 (3)C26—C25—N27—C28177.4 (3)
C5—N7—C8—N90.1 (3)C25—N27—C28—N290.0 (3)
N3—C4—N9—C8179.4 (3)N27—C28—N29—C240.0 (3)
C5—C4—N9—C80.4 (3)N27—C28—N29—C34178.2 (3)
N3—C4—N9—C146.0 (5)N23—C24—N29—C28178.9 (3)
C5—C4—N9—C14174.1 (3)C25—C24—N29—C280.0 (3)
N7—C8—N9—C40.4 (4)N23—C24—N29—C340.8 (5)
N7—C8—N9—C14174.2 (3)C25—C24—N29—C34178.2 (3)
N1—C6—N10—C110.9 (4)N21—C26—N30—C311.9 (4)
C5—C6—N10—C11179.3 (3)C25—C26—N30—C31179.9 (3)
C6—N10—C11—C1355.2 (4)C26—N30—C31—C3361.6 (4)
C6—N10—C11—C12125.8 (3)C26—N30—C31—C32131.3 (3)
N10—C11—C12—C13111.3 (3)N30—C31—C32—C33110.3 (3)
N10—C11—C13—C12106.6 (3)N30—C31—C33—C32107.1 (3)
C4—N9—C14—O15138.7 (3)C28—N29—C34—O3541.8 (4)
C8—N9—C14—O1547.9 (4)C24—N29—C34—O35140.4 (3)
C4—N9—C14—C1997.2 (4)C28—N29—C34—C3979.5 (4)
C8—N9—C14—C1976.2 (4)C24—N29—C34—C3998.3 (4)
N9—C14—O15—C16178.2 (3)N29—C34—O35—C36179.6 (3)
C19—C14—O15—C1658.1 (4)C39—C34—O35—C3659.4 (4)
C14—O15—C16—C1759.6 (5)C34—O35—C36—C3759.2 (4)
O15—C16—C17—C1856.5 (5)O35—C36—C37—C3855.5 (5)
C16—C17—C18—C1952.5 (6)C36—C37—C38—C3952.3 (5)
O15—C14—C19—C1853.9 (6)O35—C34—C39—C3855.3 (4)
N9—C14—C19—C18174.2 (4)N29—C34—C39—C38172.5 (3)
C17—C18—C19—C1450.9 (7)C37—C38—C39—C3451.9 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N10—H10···N270.862.202.998 (3)155
N30—H30···N70.862.223.023 (4)155
C36—H36B···O15i0.972.573.504 (5)162
Symmetry code: (i) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC13H16ClN5O
Mr293.76
Crystal system, space groupTriclinic, 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)
V3)1425.0 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.27
Crystal size (mm)0.15 × 0.12 × 0.10
Data collection
DiffractometerBruker SMART APEX CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.960, 0.973
No. of measured, independent and
observed [I > 2σ(I)] reflections
6270, 5203, 3410
Rint0.052
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.197, 0.97
No. of reflections5203
No. of parameters361
No. of restraints18
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.43, 0.39

Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SAINT, SHELXTL (Bruker, 2005), SHELXTL, PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N10—H10···N270.862.202.998 (3)155
N30—H30···N70.862.223.023 (4)155
C36—H36B···O15i0.972.573.504 (5)162
Symmetry code: (i) 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.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds