Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021952/xu2248sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021952/xu2248Isup2.hkl |
CCDC reference: 651403
Key indicators
- Single-crystal X-ray study
- T = 112 K
- Mean (C-C) = 0.002 Å
- R factor = 0.046
- wR factor = 0.135
- Data-to-parameter ratio = 15.2
checkCIF/PLATON results
No syntax errors found
Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.661 0.986 Tmin(prime) and Tmax expected: 0.980 0.986 RR(prime) = 0.674 Please check that your absorption correction is appropriate. PLAT031_ALERT_4_B Refined Extinction Parameter within Range ...... 1.80 Sigma PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.67
Alert level C PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 300 Deg.
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 1 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 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Most bond lengths and angles are in good agreement with those found for 6-furyl- and 6-thienyl-9-benzylpurines (Braendvang & Gundersen, 2007a; Mazumdar et al., 2001), except that the furyl ring in the title compound is rotated by approximately 180°. This orientation of the furyl ring is stabilized by C3—H3···O18 hydrogen bonding.
For related literature, see: Bakkestuen et al. (2000, 2005); Braendvang & Gundersen (2005, 2007b); Gundersen et al. (2002).
The title compound was synthesized as described by Brændvang & Gundersen (2007b). Crystals suitable for X-ray diffraction studies were obtained by slow evaporation at room temperature from a mixture of acetone and hexane (1:2).
H atoms were positioned geometrically and allowed to ride and rotate (for the CH3 group) on their carrier atoms, with C—H bond lengths of 0.95 (aromatic C—H), 0.99 (CH2) or 0.98 Å (CH3) and with Uiso(H) = 1.2Ueq(C) for methylene and aromatic C—H or 1.5Ueq(C) for CH3.
We have discovered that certain 6-aryl-9-benzylpurines are potent antimycobacterials in vitro and may have a potential as antitubercular drugs (Bakkestuen et al., 2000; Gundersen et al., 2002; Bakkestuen et al., 2005; Braendvang & Gundersen, 2005). Compound I was synthesized as a non-purine analog of the previously reported antimycobacterial purines (Braendvang & Gundersen, 2007b).
The molecular geometries are illustrated in Fig. 1 and the bond lengths and angles are listed in Table 1. The angle between the mean plane of the pyrazolo-pyrimidine ring system and the furyl ring are 0.66 (8)°. This coplanarity has also been reported for 6-arylpurines, except that the furyl ring in compound I is rotated approximately 180° compared to previously reported purine structure (Braendvang & Gundersen, 2007a). The orientation of the furyl group is stabilized by intramolecular C3–H3···O18 hydrogen bonding (Table 2). The benzene ring plane is inclined at an angle of 72.83 (7)° to the pyrazolo-pyrimidine ring system, and is very similar as in case of purine ring system previously reported (Braendvang & Gundersen, 2007a).
Fig. 2. shows the molecules in the unit cell. The molecular packing is similar to previous reported purine analog (Braendvang & Gundersen, 2007a), except that the infinite chain along [010] is linked together by hydrogen bonding C21–H21···N2i [Table 2 and Fig. 2; symmetry code: (i) x, y - 1, z] while in the previous reported structure the hydrogen bonding is between the oxygen in the furyl ring and the H8 in the purine ring.
Most bond lengths and angles are in good agreement with those found for 6-furyl- and 6-thienyl-9-benzylpurines (Braendvang & Gundersen, 2007a; Mazumdar et al., 2001), except that the furyl ring in the title compound is rotated by approximately 180°. This orientation of the furyl ring is stabilized by C3—H3···O18 hydrogen bonding.
For related literature, see: Bakkestuen et al. (2000, 2005); Braendvang & Gundersen (2005, 2007b); Gundersen et al. (2002).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and POV-RAY for Windows (Persistence of Vision Pty. Ltd, 2004); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 1999).
C17H14N4O2 | Z = 2 |
Mr = 306.32 | F(000) = 320 |
Triclinic, P1 | Dx = 1.424 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.2163 (15) Å | Cell parameters from 2969 reflections |
b = 8.4765 (15) Å | θ = 2.8–28.3° |
c = 12.437 (2) Å | µ = 0.10 mm−1 |
α = 72.485 (3)° | T = 112 K |
β = 74.209 (3)° | Block, yellow |
γ = 61.065 (3)° | 0.20 × 0.20 × 0.15 mm |
V = 714.6 (2) Å3 |
Siemens SMART CCD diffractometer | 2422 reflections with I > 2σ(I) |
ω scans | Rint = 0.025 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | θmax = 28.8°, θmin = 1.7° |
Tmin = 0.661, Tmax = 0.986 | h = −10→9 |
5825 measured reflections | k = −10→11 |
3187 independent reflections | l = −15→16 |
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0927P)2] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.046 | (Δ/σ)max < 0.001 |
wR(F2) = 0.135 | Δρmax = 0.29 e Å−3 |
S = 1.03 | Δρmin = −0.30 e Å−3 |
3187 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
210 parameters | Extinction coefficient: 0.009 (5) |
0 restraints |
C17H14N4O2 | γ = 61.065 (3)° |
Mr = 306.32 | V = 714.6 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.2163 (15) Å | Mo Kα radiation |
b = 8.4765 (15) Å | µ = 0.10 mm−1 |
c = 12.437 (2) Å | T = 112 K |
α = 72.485 (3)° | 0.20 × 0.20 × 0.15 mm |
β = 74.209 (3)° |
Siemens SMART CCD diffractometer | 3187 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2422 reflections with I > 2σ(I) |
Tmin = 0.661, Tmax = 0.986 | Rint = 0.025 |
5825 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.29 e Å−3 |
3187 reflections | Δρmin = −0.30 e Å−3 |
210 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. |
x | y | z | Uiso*/Ueq | ||
C16 | 0.0212 (2) | 1.2299 (2) | 1.00299 (13) | 0.0310 (4) | |
H16B | −0.0885 | 1.2588 | 1.0631 | 0.046* | |
H16A | −0.0199 | 1.2561 | 0.93 | 0.046* | |
H16C | 0.0847 | 1.3052 | 0.9974 | 0.046* | |
C12 | 0.3085 (2) | 0.9750 (2) | 0.95405 (12) | 0.0219 (3) | |
C13 | 0.3569 (2) | 1.0823 (2) | 0.85326 (12) | 0.0246 (3) | |
H13 | 0.2734 | 1.2083 | 0.8316 | 0.03* | |
C14 | 0.5284 (2) | 1.0031 (2) | 0.78483 (12) | 0.0243 (3) | |
H14 | 0.5622 | 1.0772 | 0.7172 | 0.029* | |
C9 | 0.6511 (2) | 0.8187 (2) | 0.81324 (12) | 0.0227 (3) | |
C10 | 0.5980 (2) | 0.7109 (2) | 0.91305 (12) | 0.0249 (3) | |
H10 | 0.6788 | 0.5835 | 0.933 | 0.03* | |
C11 | 0.4287 (2) | 0.7889 (2) | 0.98257 (12) | 0.0254 (3) | |
H11 | 0.3944 | 0.7149 | 1.0501 | 0.03* | |
C8 | 0.8340 (2) | 0.7353 (2) | 0.73554 (13) | 0.0277 (4) | |
H8B | 0.8838 | 0.8279 | 0.7005 | 0.033* | |
H8A | 0.9272 | 0.6296 | 0.7814 | 0.033* | |
C3 | 0.7299 (2) | 0.7047 (2) | 0.48624 (12) | 0.0238 (3) | |
H3 | 0.6905 | 0.7563 | 0.4133 | 0.029* | |
C3A | 0.7731 (2) | 0.5197 (2) | 0.54462 (11) | 0.0199 (3) | |
C4 | 0.7772 (2) | 0.3590 (2) | 0.53073 (11) | 0.0201 (3) | |
C6 | 0.8695 (2) | 0.2165 (2) | 0.70764 (12) | 0.0277 (4) | |
H6 | 0.9036 | 0.1068 | 0.7644 | 0.033* | |
C7A | 0.8228 (2) | 0.5069 (2) | 0.64762 (12) | 0.0212 (3) | |
C17 | 0.7315 (2) | 0.3450 (2) | 0.43035 (11) | 0.0209 (3) | |
C19 | 0.6430 (2) | 0.4520 (2) | 0.26199 (13) | 0.0283 (4) | |
H19 | 0.6031 | 0.5326 | 0.1925 | 0.034* | |
C20 | 0.6719 (2) | 0.2745 (2) | 0.29123 (12) | 0.0279 (4) | |
H20 | 0.6569 | 0.2094 | 0.2473 | 0.033* | |
C21 | 0.7291 (2) | 0.2044 (2) | 0.40082 (12) | 0.0249 (3) | |
H21 | 0.7595 | 0.0833 | 0.4447 | 0.03* | |
N1 | 0.81128 (18) | 0.67308 (17) | 0.64542 (10) | 0.0239 (3) | |
N2 | 0.75177 (19) | 0.79507 (17) | 0.54690 (10) | 0.0260 (3) | |
N5 | 0.82546 (19) | 0.20712 (17) | 0.61400 (10) | 0.0251 (3) | |
N7 | 0.87220 (19) | 0.35803 (18) | 0.73238 (10) | 0.0256 (3) | |
O15 | 0.14786 (15) | 1.04026 (15) | 1.02991 (8) | 0.0279 (3) | |
O18 | 0.67872 (15) | 0.50055 (14) | 0.34530 (8) | 0.0254 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C16 | 0.0294 (9) | 0.0345 (9) | 0.0258 (8) | −0.0120 (8) | −0.0011 (7) | −0.0081 (7) |
C12 | 0.0244 (8) | 0.0289 (8) | 0.0170 (6) | −0.0158 (7) | −0.0021 (6) | −0.0044 (6) |
C13 | 0.0308 (9) | 0.0220 (8) | 0.0221 (7) | −0.0144 (7) | −0.0035 (6) | −0.0012 (6) |
C14 | 0.0331 (9) | 0.0273 (8) | 0.0190 (7) | −0.0208 (7) | −0.0018 (6) | −0.0018 (6) |
C9 | 0.0267 (8) | 0.0288 (8) | 0.0210 (7) | −0.0172 (7) | −0.0035 (6) | −0.0075 (6) |
C10 | 0.0295 (8) | 0.0226 (8) | 0.0240 (7) | −0.0118 (7) | −0.0087 (6) | −0.0015 (6) |
C11 | 0.0316 (9) | 0.0293 (8) | 0.0175 (6) | −0.0183 (7) | −0.0061 (6) | 0.0030 (6) |
C8 | 0.0272 (8) | 0.0357 (9) | 0.0288 (8) | −0.0184 (7) | −0.0011 (6) | −0.0128 (7) |
C3 | 0.0287 (8) | 0.0240 (8) | 0.0193 (7) | −0.0152 (7) | −0.0024 (6) | 0.0000 (6) |
C3A | 0.0218 (7) | 0.0218 (7) | 0.0161 (6) | −0.0121 (6) | −0.0004 (5) | −0.0017 (5) |
C4 | 0.0224 (7) | 0.0216 (7) | 0.0168 (6) | −0.0130 (6) | 0.0002 (5) | −0.0012 (5) |
C6 | 0.0370 (9) | 0.0261 (8) | 0.0181 (7) | −0.0160 (7) | −0.0045 (6) | 0.0023 (6) |
C7A | 0.0225 (8) | 0.0243 (8) | 0.0183 (7) | −0.0133 (6) | 0.0010 (6) | −0.0044 (6) |
C17 | 0.0225 (8) | 0.0230 (8) | 0.0172 (6) | −0.0135 (6) | −0.0009 (6) | 0.0000 (6) |
C19 | 0.0331 (9) | 0.0377 (9) | 0.0190 (7) | −0.0202 (8) | −0.0055 (6) | −0.0028 (6) |
C20 | 0.0329 (9) | 0.0377 (9) | 0.0223 (7) | −0.0229 (8) | −0.0005 (6) | −0.0088 (7) |
C21 | 0.0300 (8) | 0.0260 (8) | 0.0220 (7) | −0.0169 (7) | −0.0008 (6) | −0.0037 (6) |
N1 | 0.0294 (7) | 0.0250 (7) | 0.0210 (6) | −0.0157 (6) | −0.0024 (5) | −0.0044 (5) |
N2 | 0.0321 (7) | 0.0233 (7) | 0.0239 (6) | −0.0159 (6) | −0.0029 (5) | −0.0012 (5) |
N5 | 0.0339 (7) | 0.0239 (7) | 0.0184 (6) | −0.0166 (6) | −0.0032 (5) | 0.0009 (5) |
N7 | 0.0327 (7) | 0.0269 (7) | 0.0176 (6) | −0.0151 (6) | −0.0046 (5) | −0.0007 (5) |
O15 | 0.0262 (6) | 0.0327 (6) | 0.0193 (5) | −0.0124 (5) | −0.0004 (4) | −0.0016 (4) |
O18 | 0.0357 (6) | 0.0242 (6) | 0.0185 (5) | −0.0168 (5) | −0.0071 (4) | 0.0019 (4) |
C16—O15 | 1.423 (2) | C3—N2 | 1.3199 (19) |
C16—H16B | 0.98 | C3—C3A | 1.425 (2) |
C16—H16A | 0.98 | C3—H3 | 0.95 |
C16—H16C | 0.98 | C3A—C7A | 1.4063 (19) |
C12—O15 | 1.3669 (18) | C3A—C4 | 1.407 (2) |
C12—C11 | 1.392 (2) | C4—N5 | 1.3470 (18) |
C12—C13 | 1.396 (2) | C6—N7 | 1.336 (2) |
C13—C14 | 1.392 (2) | C6—N5 | 1.344 (2) |
C13—H13 | 0.95 | C6—H6 | 0.95 |
C14—C9 | 1.386 (2) | C7A—N7 | 1.3437 (18) |
C14—H14 | 0.95 | C7A—N1 | 1.3574 (18) |
C9—C10 | 1.405 (2) | C17—C21 | 1.358 (2) |
N1—C8 | 1.4610 (18) | C17—O18 | 1.3793 (16) |
C4—C17 | 1.4494 (19) | C19—C20 | 1.351 (2) |
C8—C9 | 1.512 (2) | C19—O18 | 1.3667 (18) |
C10—C11 | 1.385 (2) | C19—H19 | 0.95 |
C10—H10 | 0.95 | C20—C21 | 1.422 (2) |
C11—H11 | 0.95 | C20—H20 | 0.95 |
C8—H8B | 0.99 | C21—H21 | 0.95 |
C8—H8A | 0.99 | N1—N2 | 1.3726 (17) |
O15—C16—H16B | 109.5 | C7A—C3A—C4 | 115.70 (13) |
O15—C16—H16A | 109.5 | C7A—C3A—C3 | 104.23 (12) |
H16B—C16—H16A | 109.5 | C4—C3A—C3 | 140.06 (13) |
O15—C16—H16C | 109.5 | N5—C4—C3A | 119.68 (13) |
H16B—C16—H16C | 109.5 | N5—C4—C17 | 116.53 (13) |
H16A—C16—H16C | 109.5 | C3A—C4—C17 | 123.80 (13) |
O15—C12—C11 | 115.94 (13) | N7—C6—N5 | 129.32 (14) |
O15—C12—C13 | 124.37 (14) | N7—C6—H6 | 115.3 |
C11—C12—C13 | 119.68 (14) | N5—C6—H6 | 115.3 |
C14—C13—C12 | 119.47 (14) | N7—C7A—N1 | 126.44 (13) |
C14—C13—H13 | 120.3 | N7—C7A—C3A | 126.35 (13) |
C12—C13—H13 | 120.3 | N1—C7A—C3A | 107.22 (13) |
C9—C14—C13 | 121.45 (14) | C21—C17—O18 | 110.44 (12) |
C9—C14—H14 | 119.3 | C21—C17—C4 | 132.49 (14) |
C13—C14—H14 | 119.3 | O18—C17—C4 | 117.07 (12) |
C14—C9—C10 | 118.51 (14) | C20—C19—O18 | 111.19 (13) |
C14—C9—C8 | 120.25 (14) | C20—C19—H19 | 124.4 |
C10—C9—C8 | 121.19 (14) | O18—C19—H19 | 124.4 |
C11—C10—C9 | 120.49 (15) | C19—C20—C21 | 106.41 (13) |
C11—C10—H10 | 119.8 | C19—C20—H20 | 126.8 |
C9—C10—H10 | 119.8 | C21—C20—H20 | 126.8 |
C10—C11—C12 | 120.35 (14) | C17—C21—C20 | 106.38 (13) |
C10—C11—H11 | 119.8 | C17—C21—H21 | 126.8 |
C12—C11—H11 | 119.8 | C20—C21—H21 | 126.8 |
N1—C8—C9 | 112.29 (12) | C7A—N1—N2 | 110.83 (12) |
N1—C8—H8B | 109.1 | C7A—N1—C8 | 128.64 (13) |
C9—C8—H8B | 109.1 | N2—N1—C8 | 120.17 (12) |
N1—C8—H8A | 109.1 | C3—N2—N1 | 106.67 (12) |
C9—C8—H8A | 109.1 | C6—N5—C4 | 117.58 (13) |
H8B—C8—H8A | 107.9 | C6—N7—C7A | 111.38 (12) |
N2—C3—C3A | 111.02 (13) | C12—O15—C16 | 117.41 (12) |
N2—C3—H3 | 124.5 | C19—O18—C17 | 105.58 (11) |
C3A—C3—H3 | 124.5 | ||
O15—C12—C13—C14 | 177.07 (13) | C3A—C4—C17—O18 | −1.0 (2) |
C11—C12—C13—C14 | −2.6 (2) | O18—C19—C20—C21 | 0.29 (18) |
C12—C13—C14—C9 | 1.4 (2) | O18—C17—C21—C20 | 0.04 (17) |
C13—C14—C9—C10 | 0.6 (2) | C4—C17—C21—C20 | 179.89 (15) |
C13—C14—C9—C8 | 178.30 (13) | C19—C20—C21—C17 | −0.20 (17) |
C14—C9—C10—C11 | −1.5 (2) | N7—C7A—N1—N2 | −178.42 (13) |
C8—C9—C10—C11 | −179.15 (13) | C3A—C7A—N1—N2 | 1.53 (16) |
C9—C10—C11—C12 | 0.3 (2) | N7—C7A—N1—C8 | −5.4 (2) |
O15—C12—C11—C10 | −177.94 (12) | C3A—C7A—N1—C8 | 174.58 (14) |
C13—C12—C11—C10 | 1.7 (2) | C9—C8—N1—C7A | −88.40 (19) |
C14—C9—C8—N1 | −85.88 (17) | C9—C8—N1—N2 | 84.09 (17) |
C10—C9—C8—N1 | 91.74 (17) | C3A—C3—N2—N1 | 0.61 (17) |
N2—C3—C3A—C7A | 0.28 (17) | C7A—N1—N2—C3 | −1.34 (16) |
N2—C3—C3A—C4 | 179.00 (18) | C8—N1—N2—C3 | −175.07 (13) |
C7A—C3A—C4—N5 | 0.4 (2) | N7—C6—N5—C4 | 0.4 (3) |
C3—C3A—C4—N5 | −178.22 (17) | C3A—C4—N5—C6 | −0.5 (2) |
C7A—C3A—C4—C17 | −179.69 (13) | C17—C4—N5—C6 | 179.62 (13) |
C3—C3A—C4—C17 | 1.7 (3) | N5—C6—N7—C7A | −0.2 (2) |
C4—C3A—C7A—N7 | −0.2 (2) | N1—C7A—N7—C6 | −179.97 (14) |
C3—C3A—C7A—N7 | 178.87 (14) | C3A—C7A—N7—C6 | 0.1 (2) |
C4—C3A—C7A—N1 | 179.84 (12) | C11—C12—O15—C16 | −179.58 (13) |
C3—C3A—C7A—N1 | −1.08 (16) | C13—C12—O15—C16 | 0.8 (2) |
N5—C4—C17—C21 | −0.9 (2) | C20—C19—O18—C17 | −0.27 (17) |
C3A—C4—C17—C21 | 179.19 (15) | C21—C17—O18—C19 | 0.13 (16) |
N5—C4—C17—O18 | 178.94 (12) | C4—C17—O18—C19 | −179.74 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H21···N2i | 0.95 | 2.41 | 3.338 (2) | 164 |
C16—H16A···N7ii | 0.98 | 2.60 | 3.572 (2) | 174 |
C3—H3···O18 | 0.95 | 2.60 | 3.029 (2) | 108 |
C6—H6···O15iii | 0.95 | 2.51 | 3.344 (2) | 147 |
Symmetry codes: (i) x, y−1, z; (ii) x−1, y+1, z; (iii) −x+1, −y+1, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C17H14N4O2 |
Mr | 306.32 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 112 |
a, b, c (Å) | 8.2163 (15), 8.4765 (15), 12.437 (2) |
α, β, γ (°) | 72.485 (3), 74.209 (3), 61.065 (3) |
V (Å3) | 714.6 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.20 × 0.20 × 0.15 |
Data collection | |
Diffractometer | Siemens SMART CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.661, 0.986 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5825, 3187, 2422 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.678 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.135, 1.03 |
No. of reflections | 3187 |
No. of parameters | 210 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.30 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997) and POV-RAY for Windows (Persistence of Vision Pty. Ltd, 2004), SHELXL97 and WinGX (Farrugia, 1999).
N1—C8 | 1.4610 (18) | C8—C9 | 1.512 (2) |
C4—C17 | 1.4494 (19) | ||
C12—O15—C16 | 117.41 (12) | ||
C10—C9—C8—N1 | 91.74 (17) | C13—C12—O15—C16 | 0.8 (2) |
C9—C8—N1—C7A | −88.40 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H21···N2i | 0.95 | 2.41 | 3.338 (2) | 164 |
C16—H16A···N7ii | 0.98 | 2.60 | 3.572 (2) | 174 |
C3—H3···O18 | 0.95 | 2.60 | 3.029 (2) | 108 |
C6—H6···O15iii | 0.95 | 2.51 | 3.344 (2) | 147 |
Symmetry codes: (i) x, y−1, z; (ii) x−1, y+1, z; (iii) −x+1, −y+1, −z+2. |
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We have discovered that certain 6-aryl-9-benzylpurines are potent antimycobacterials in vitro and may have a potential as antitubercular drugs (Bakkestuen et al., 2000; Gundersen et al., 2002; Bakkestuen et al., 2005; Braendvang & Gundersen, 2005). Compound I was synthesized as a non-purine analog of the previously reported antimycobacterial purines (Braendvang & Gundersen, 2007b).
The molecular geometries are illustrated in Fig. 1 and the bond lengths and angles are listed in Table 1. The angle between the mean plane of the pyrazolo-pyrimidine ring system and the furyl ring are 0.66 (8)°. This coplanarity has also been reported for 6-arylpurines, except that the furyl ring in compound I is rotated approximately 180° compared to previously reported purine structure (Braendvang & Gundersen, 2007a). The orientation of the furyl group is stabilized by intramolecular C3–H3···O18 hydrogen bonding (Table 2). The benzene ring plane is inclined at an angle of 72.83 (7)° to the pyrazolo-pyrimidine ring system, and is very similar as in case of purine ring system previously reported (Braendvang & Gundersen, 2007a).
Fig. 2. shows the molecules in the unit cell. The molecular packing is similar to previous reported purine analog (Braendvang & Gundersen, 2007a), except that the infinite chain along [010] is linked together by hydrogen bonding C21–H21···N2i [Table 2 and Fig. 2; symmetry code: (i) x, y - 1, z] while in the previous reported structure the hydrogen bonding is between the oxygen in the furyl ring and the H8 in the purine ring.