Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807056760/lh2551sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807056760/lh2551Isup2.hkl |
CCDC reference: 672927
Key indicators
- Single-crystal X-ray study
- T = 103 K
- Mean (C-C) = 0.006 Å
- R factor = 0.060
- wR factor = 0.137
- Data-to-parameter ratio = 9.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C6 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C11
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.48 From the CIF: _reflns_number_total 2647 Count of symmetry unique reflns 2659 Completeness (_total/calc) 99.55% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C21 = . R PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 5 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 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The structures of the analogous 1,2,4-triazole and tetrazole nucleosides have been reported recently (Müller et al., 2005). These nucleosides have been used in metal-ion-mediated base pairs (Böhme et al., 2007). For related literature, see: Polonius & Müller (2007); Müller et al. (2007); Allen et al. (1987); Farrugia (1997, 1999); Flack (1983).
The title compound was prepared as reported previously (Müller et al., 2005). Single crystals suitable for X-ray measurement were obtained by crystallization from dichloromethane and cyclohexane with triethylamine at room temperature. A satisfactory elemental analysis was obtained: Calcd. for C24H24N2O5: C 68.6, H 5.8, N 6.7; found: C 68.2, H 6.2, N 6.6.
In the absence of significant anomalous dispersion effects, a total of 1277 Friedel pairs have been merged during the final refinement.
Hydrogen atoms were included in the refinement at calculated positions with C—H = 0.95–1.00 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) for methyl groups.
Data collection: KappaCCD (Nonius, 2000); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. View of the title compound showing displacement ellipsoids at the 50% probability level. | |
Fig. 2. Packing of the title compound with a view along the b axis. |
C24H24N2O5 | Z = 2 |
Mr = 420.45 | F(000) = 444 |
Monoclinic, P21 | Dx = 1.33 Mg m−3 |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 14.436 (3) Å | θ = 3–27.5° |
b = 5.3850 (11) Å | µ = 0.09 mm−1 |
c = 15.061 (3) Å | T = 103 K |
β = 116.25 (3)° | Cubes, colorless |
V = 1050.1 (5) Å3 | 0.1 × 0.1 × 0.1 mm |
Bruker–Nonius Kappa CCD diffractometer | Rint = 0.097 |
profile fitled scans | θmax = 27.5°, θmin = 3.0° |
12891 measured reflections | h = −18→18 |
2647 independent reflections | k = −7→5 |
1726 reflections with I > 2σ(I) | l = −19→19 |
Refinement on F2 | 1 restraint |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.060 | w = 1/[σ2(Fo2) + (0.0694P)2 + 0.2112P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.137 | (Δ/σ)max < 0.001 |
S = 1.01 | Δρmax = 0.28 e Å−3 |
2647 reflections | Δρmin = −0.34 e Å−3 |
280 parameters |
C24H24N2O5 | V = 1050.1 (5) Å3 |
Mr = 420.45 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 14.436 (3) Å | µ = 0.09 mm−1 |
b = 5.3850 (11) Å | T = 103 K |
c = 15.061 (3) Å | 0.1 × 0.1 × 0.1 mm |
β = 116.25 (3)° |
Bruker–Nonius Kappa CCD diffractometer | 1726 reflections with I > 2σ(I) |
12891 measured reflections | Rint = 0.097 |
2647 independent reflections |
R[F2 > 2σ(F2)] = 0.060 | 1 restraint |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.28 e Å−3 |
2647 reflections | Δρmin = −0.34 e Å−3 |
280 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 | ||
O30 | 0.3603 (2) | 0.8395 (6) | 0.96544 (19) | 0.0222 (7) | |
N29 | 0.1239 (2) | 1.0452 (6) | 0.9936 (2) | 0.0200 (8) | |
O28 | 0.44002 (19) | 0.7940 (6) | 1.24729 (19) | 0.0221 (7) | |
O27 | 0.4201 (2) | 0.9804 (6) | 0.8587 (2) | 0.0259 (7) | |
C26 | 0.5335 (3) | 0.5234 (8) | 1.3793 (3) | 0.0200 (9) | |
C25 | 0.0239 (3) | 0.8334 (9) | 0.8628 (3) | 0.0268 (10) | |
H25A | −0.0014 | 0.7064 | 0.8141 | 0.032* | |
C24 | 0.6206 (3) | 0.6745 (9) | 1.4091 (3) | 0.0267 (11) | |
H24A | 0.6179 | 0.822 | 1.3734 | 0.032* | |
N23 | −0.0292 (3) | 1.0479 (8) | 0.8608 (3) | 0.0303 (9) | |
C22 | 0.1929 (3) | 0.5296 (8) | 0.6379 (3) | 0.0242 (10) | |
H22A | 0.1737 | 0.5516 | 0.5694 | 0.029* | |
C21 | 0.2101 (3) | 1.1388 (8) | 1.0832 (3) | 0.0205 (10) | |
H21A | 0.1866 | 1.2855 | 1.1085 | 0.025* | |
C20 | 0.2901 (3) | 0.6638 (8) | 0.8066 (3) | 0.0196 (9) | |
C19 | 0.0339 (3) | 1.1715 (9) | 0.9398 (3) | 0.0249 (10) | |
H19A | 0.0187 | 1.3304 | 0.9575 | 0.03* | |
O18 | 0.3571 (2) | 0.4591 (6) | 1.2656 (2) | 0.0262 (7) | |
C17 | 0.1172 (3) | 0.8278 (9) | 0.9437 (3) | 0.0256 (10) | |
H17A | 0.1675 | 0.6995 | 0.962 | 0.031* | |
C16 | 0.7183 (3) | 0.3957 (9) | 1.5446 (3) | 0.0283 (12) | |
C15 | 0.2466 (3) | 0.4697 (8) | 0.8370 (3) | 0.0214 (9) | |
H15A | 0.2654 | 0.4478 | 0.9054 | 0.026* | |
C14 | 0.5391 (3) | 0.3097 (9) | 1.4337 (3) | 0.0257 (10) | |
H14A | 0.48 | 0.2064 | 1.4147 | 0.031* | |
C13 | 0.3831 (3) | 1.0697 (8) | 1.1102 (3) | 0.0194 (9) | |
H13A | 0.4338 | 1.1726 | 1.1657 | 0.023* | |
C12 | 0.4342 (3) | 0.5834 (8) | 1.2935 (3) | 0.0209 (10) | |
C11 | 0.8179 (3) | 0.3260 (12) | 1.6335 (3) | 0.0429 (14) | |
H11A | 0.8709 | 0.4508 | 1.6431 | 0.064* | |
H11B | 0.8412 | 0.1632 | 1.6223 | 0.064* | |
H11C | 0.8059 | 0.3188 | 1.6927 | 0.064* | |
C10 | 0.1487 (3) | 0.3368 (9) | 0.6677 (3) | 0.0245 (10) | |
C9 | 0.1769 (3) | 0.3097 (9) | 0.7689 (3) | 0.0261 (10) | |
H9A | 0.1477 | 0.1794 | 0.7907 | 0.031* | |
C8 | 0.3638 (3) | 0.8416 (9) | 0.8767 (3) | 0.0220 (9) | |
C7 | 0.3513 (3) | 0.8494 (8) | 1.1542 (3) | 0.0180 (9) | |
H7A | 0.3321 | 0.7032 | 1.1087 | 0.022* | |
C6 | 0.0724 (3) | 0.1619 (9) | 0.5931 (3) | 0.0337 (12) | |
H6A | 0.0619 | 0.2086 | 0.5265 | 0.051* | |
H6B | 0.0064 | 0.1713 | 0.5969 | 0.051* | |
H6C | 0.0991 | −0.0082 | 0.6075 | 0.051* | |
C5 | 0.6310 (3) | 0.2462 (9) | 1.5159 (3) | 0.0299 (11) | |
H5A | 0.634 | 0.1001 | 1.5524 | 0.036* | |
C4 | 0.2640 (3) | 0.6893 (9) | 0.7056 (3) | 0.0266 (10) | |
H4A | 0.295 | 0.8159 | 0.6838 | 0.032* | |
C3 | 0.4296 (3) | 1.0075 (9) | 1.0408 (3) | 0.0234 (10) | |
H3A | 0.4392 | 1.1609 | 1.0096 | 0.028* | |
H3B | 0.4979 | 0.9279 | 1.0779 | 0.028* | |
C2 | 0.7116 (3) | 0.6093 (10) | 1.4912 (3) | 0.0315 (12) | |
H2A | 0.7703 | 0.714 | 1.511 | 0.038* | |
C1 | 0.2577 (3) | 0.9476 (9) | 1.1657 (3) | 0.0199 (9) | |
H1A | 0.2082 | 0.8122 | 1.1576 | 0.024* | |
H1B | 0.2792 | 1.0256 | 1.2314 | 0.024* | |
O31 | 0.2904 (2) | 1.2143 (5) | 1.05768 (19) | 0.0208 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O30 | 0.0189 (14) | 0.0291 (16) | 0.0216 (15) | −0.0078 (14) | 0.0116 (12) | −0.0057 (14) |
N29 | 0.0149 (17) | 0.0197 (19) | 0.0251 (18) | −0.0006 (16) | 0.0087 (15) | −0.0016 (16) |
O28 | 0.0160 (14) | 0.0252 (16) | 0.0221 (15) | 0.0017 (13) | 0.0057 (12) | 0.0027 (13) |
O27 | 0.0230 (15) | 0.0327 (19) | 0.0266 (16) | −0.0017 (15) | 0.0153 (13) | −0.0005 (15) |
C26 | 0.022 (2) | 0.022 (2) | 0.020 (2) | 0.0020 (19) | 0.0131 (18) | −0.0048 (18) |
C25 | 0.023 (2) | 0.027 (2) | 0.029 (2) | −0.003 (2) | 0.010 (2) | −0.001 (2) |
C24 | 0.021 (2) | 0.032 (3) | 0.029 (2) | 0.001 (2) | 0.014 (2) | −0.001 (2) |
N23 | 0.0244 (19) | 0.033 (2) | 0.027 (2) | −0.0011 (19) | 0.0055 (17) | 0.0014 (19) |
C22 | 0.026 (2) | 0.025 (3) | 0.022 (2) | 0.005 (2) | 0.0110 (19) | −0.001 (2) |
C21 | 0.014 (2) | 0.023 (2) | 0.027 (2) | −0.0015 (19) | 0.0100 (18) | 0.001 (2) |
C20 | 0.016 (2) | 0.023 (2) | 0.022 (2) | 0.006 (2) | 0.0095 (18) | 0.000 (2) |
C19 | 0.017 (2) | 0.026 (2) | 0.033 (2) | 0.007 (2) | 0.012 (2) | 0.006 (2) |
O18 | 0.0247 (16) | 0.0233 (16) | 0.0275 (16) | −0.0036 (15) | 0.0087 (13) | 0.0007 (15) |
C17 | 0.020 (2) | 0.028 (2) | 0.027 (2) | 0.001 (2) | 0.009 (2) | −0.001 (2) |
C16 | 0.025 (2) | 0.043 (3) | 0.019 (2) | 0.011 (2) | 0.010 (2) | 0.001 (2) |
C15 | 0.022 (2) | 0.026 (2) | 0.018 (2) | 0.004 (2) | 0.0107 (18) | 0.005 (2) |
C14 | 0.026 (2) | 0.026 (2) | 0.026 (2) | 0.004 (2) | 0.012 (2) | 0.001 (2) |
C13 | 0.016 (2) | 0.021 (2) | 0.021 (2) | 0.0005 (18) | 0.0076 (17) | −0.0008 (19) |
C12 | 0.025 (2) | 0.018 (2) | 0.021 (2) | 0.006 (2) | 0.0122 (19) | 0.002 (2) |
C11 | 0.026 (2) | 0.066 (4) | 0.034 (3) | 0.019 (3) | 0.012 (2) | 0.010 (3) |
C10 | 0.017 (2) | 0.025 (2) | 0.028 (2) | 0.007 (2) | 0.0070 (19) | 0.001 (2) |
C9 | 0.021 (2) | 0.026 (2) | 0.035 (2) | 0.005 (2) | 0.016 (2) | 0.000 (2) |
C8 | 0.018 (2) | 0.028 (2) | 0.024 (2) | 0.006 (2) | 0.0132 (19) | 0.002 (2) |
C7 | 0.0150 (19) | 0.023 (2) | 0.017 (2) | −0.0027 (19) | 0.0075 (17) | 0.0003 (19) |
C6 | 0.024 (2) | 0.033 (3) | 0.036 (3) | 0.001 (2) | 0.006 (2) | −0.003 (2) |
C5 | 0.034 (3) | 0.035 (3) | 0.025 (2) | 0.009 (2) | 0.017 (2) | 0.010 (2) |
C4 | 0.024 (2) | 0.033 (3) | 0.028 (2) | 0.003 (2) | 0.016 (2) | 0.002 (2) |
C3 | 0.018 (2) | 0.029 (3) | 0.025 (2) | −0.004 (2) | 0.0101 (18) | −0.001 (2) |
C2 | 0.024 (2) | 0.044 (3) | 0.025 (2) | −0.002 (2) | 0.010 (2) | 0.000 (2) |
C1 | 0.0130 (19) | 0.026 (2) | 0.023 (2) | −0.0015 (19) | 0.0096 (17) | 0.000 (2) |
O31 | 0.0145 (14) | 0.0247 (16) | 0.0266 (15) | 0.0009 (13) | 0.0123 (12) | 0.0029 (13) |
O30—C8 | 1.360 (5) | C16—C2 | 1.382 (6) |
O30—C3 | 1.450 (5) | C16—C5 | 1.393 (7) |
N29—C19 | 1.370 (5) | C16—C11 | 1.516 (6) |
N29—C17 | 1.371 (6) | C15—C9 | 1.377 (6) |
N29—C21 | 1.462 (5) | C15—H15A | 0.95 |
O28—C12 | 1.352 (5) | C14—C5 | 1.400 (6) |
O28—C7 | 1.451 (4) | C14—H14A | 0.95 |
O27—C8 | 1.220 (5) | C13—O31 | 1.445 (5) |
C26—C14 | 1.394 (6) | C13—C3 | 1.509 (5) |
C26—C24 | 1.395 (6) | C13—C7 | 1.525 (6) |
C26—C12 | 1.480 (5) | C13—H13A | 1 |
C25—C17 | 1.360 (6) | C11—H11A | 0.98 |
C25—N23 | 1.379 (6) | C11—H11B | 0.98 |
C25—H25A | 0.95 | C11—H11C | 0.98 |
C24—C2 | 1.393 (6) | C10—C9 | 1.400 (6) |
C24—H24A | 0.95 | C10—C6 | 1.506 (6) |
N23—C19 | 1.315 (6) | C9—H9A | 0.95 |
C22—C4 | 1.381 (6) | C7—C1 | 1.530 (6) |
C22—C10 | 1.393 (6) | C7—H7A | 1 |
C22—H22A | 0.95 | C6—H6A | 0.98 |
C21—O31 | 1.432 (5) | C6—H6B | 0.98 |
C21—C1 | 1.523 (6) | C6—H6C | 0.98 |
C21—H21A | 1 | C5—H5A | 0.95 |
C20—C15 | 1.396 (6) | C4—H4A | 0.95 |
C20—C4 | 1.404 (5) | C3—H3A | 0.99 |
C20—C8 | 1.473 (6) | C3—H3B | 0.99 |
C19—H19A | 0.95 | C2—H2A | 0.95 |
O18—C12 | 1.205 (5) | C1—H1A | 0.99 |
C17—H17A | 0.95 | C1—H1B | 0.99 |
C8—O30—C3 | 116.8 (3) | O28—C12—C26 | 112.1 (4) |
C19—N29—C17 | 106.3 (3) | C16—C11—H11A | 109.5 |
C19—N29—C21 | 124.9 (4) | C16—C11—H11B | 109.5 |
C17—N29—C21 | 128.7 (3) | H11A—C11—H11B | 109.5 |
C12—O28—C7 | 116.1 (3) | C16—C11—H11C | 109.5 |
C14—C26—C24 | 118.9 (4) | H11A—C11—H11C | 109.5 |
C14—C26—C12 | 118.3 (4) | H11B—C11—H11C | 109.5 |
C24—C26—C12 | 122.7 (4) | C22—C10—C9 | 118.3 (4) |
C17—C25—N23 | 111.0 (4) | C22—C10—C6 | 121.0 (4) |
C17—C25—H25A | 124.5 | C9—C10—C6 | 120.7 (4) |
N23—C25—H25A | 124.5 | C15—C9—C10 | 120.7 (4) |
C2—C24—C26 | 120.0 (4) | C15—C9—H9A | 119.6 |
C2—C24—H24A | 120 | C10—C9—H9A | 119.6 |
C26—C24—H24A | 120 | O27—C8—O30 | 122.8 (4) |
C19—N23—C25 | 104.4 (4) | O27—C8—C20 | 125.5 (4) |
C4—C22—C10 | 121.5 (4) | O30—C8—C20 | 111.7 (4) |
C4—C22—H22A | 119.2 | O28—C7—C13 | 105.9 (3) |
C10—C22—H22A | 119.2 | O28—C7—C1 | 114.1 (3) |
O31—C21—N29 | 108.0 (3) | C13—C7—C1 | 103.3 (3) |
O31—C21—C1 | 106.5 (3) | O28—C7—H7A | 111 |
N29—C21—C1 | 114.4 (4) | C13—C7—H7A | 111 |
O31—C21—H21A | 109.3 | C1—C7—H7A | 111 |
N29—C21—H21A | 109.3 | C10—C6—H6A | 109.5 |
C1—C21—H21A | 109.3 | C10—C6—H6B | 109.5 |
C15—C20—C4 | 119.0 (4) | H6A—C6—H6B | 109.5 |
C15—C20—C8 | 122.6 (4) | C10—C6—H6C | 109.5 |
C4—C20—C8 | 118.4 (4) | H6A—C6—H6C | 109.5 |
N23—C19—N29 | 112.3 (4) | H6B—C6—H6C | 109.5 |
N23—C19—H19A | 123.8 | C16—C5—C14 | 120.5 (4) |
N29—C19—H19A | 123.8 | C16—C5—H5A | 119.8 |
C25—C17—N29 | 105.9 (4) | C14—C5—H5A | 119.8 |
C25—C17—H17A | 127.1 | C22—C4—C20 | 119.7 (4) |
N29—C17—H17A | 127.1 | C22—C4—H4A | 120.2 |
C2—C16—C5 | 118.6 (4) | C20—C4—H4A | 120.2 |
C2—C16—C11 | 121.0 (5) | O30—C3—C13 | 108.4 (3) |
C5—C16—C11 | 120.3 (4) | O30—C3—H3A | 110 |
C9—C15—C20 | 120.7 (4) | C13—C3—H3A | 110 |
C9—C15—H15A | 119.6 | O30—C3—H3B | 110 |
C20—C15—H15A | 119.6 | C13—C3—H3B | 110 |
C26—C14—C5 | 120.4 (4) | H3A—C3—H3B | 108.4 |
C26—C14—H14A | 119.8 | C16—C2—C24 | 121.5 (5) |
C5—C14—H14A | 119.8 | C16—C2—H2A | 119.2 |
O31—C13—C3 | 109.2 (3) | C24—C2—H2A | 119.2 |
O31—C13—C7 | 105.8 (3) | C21—C1—C7 | 104.1 (3) |
C3—C13—C7 | 116.1 (4) | C21—C1—H1A | 110.9 |
O31—C13—H13A | 108.5 | C7—C1—H1A | 110.9 |
C3—C13—H13A | 108.5 | C21—C1—H1B | 110.9 |
C7—C13—H13A | 108.5 | C7—C1—H1B | 110.9 |
O18—C12—O28 | 123.0 (4) | H1A—C1—H1B | 109 |
O18—C12—C26 | 124.9 (4) | C21—O31—C13 | 111.3 (3) |
C12—O28—C7—C1 | 75.4 (5) | C22—C4—C20—C8 | −178.2 (4) |
C12—O28—C7—C13 | −171.7 (3) | C22—C4—C20—C15 | 2.7 (7) |
C7—O28—C12—O18 | −7.0 (6) | C20—C4—C22—C10 | −2.3 (7) |
C7—O28—C12—C26 | 171.5 (3) | C14—C5—C16—C2 | 1.0 (7) |
C8—O30—C3—C13 | 153.6 (4) | C14—C5—C16—C11 | −179.8 (4) |
C3—O30—C8—O27 | −1.7 (6) | C16—C5—C14—C26 | 0.0 (7) |
C3—O30—C8—C20 | 180.0 (4) | O28—C7—C13—O31 | −146.7 (3) |
C21—O31—C13—C3 | 139.0 (4) | O28—C7—C13—C3 | 92.0 (4) |
C21—O31—C13—C7 | 13.4 (4) | C1—C7—C13—O31 | −26.5 (4) |
C13—O31—C21—N29 | −117.7 (3) | C1—C7—C13—C3 | −147.8 (4) |
C13—O31—C21—C1 | 5.6 (4) | O30—C8—C20—C15 | −17.9 (6) |
C19—N23—C25—C17 | 1.3 (5) | O27—C8—C20—C15 | 163.9 (5) |
C25—N23—C19—N29 | −1.3 (5) | O30—C8—C20—C4 | 163.0 (4) |
C19—N29—C17—C25 | 0.0 (5) | O27—C8—C20—C4 | −15.2 (7) |
C19—N29—C21—O31 | −104.2 (4) | C15—C9—C10—C6 | −180.0 (4) |
C19—N29—C21—C1 | 137.4 (4) | C10—C9—C15—C20 | 0.5 (7) |
C21—N29—C19—N23 | 177.9 (4) | C15—C9—C10—C22 | 0.0 (7) |
C21—N29—C17—C25 | −176.9 (4) | C6—C10—C22—C4 | −179.1 (4) |
C17—N29—C19—N23 | 0.9 (5) | C9—C10—C22—C4 | 1.0 (7) |
C17—N29—C21—O31 | 72.1 (5) | O18—C12—C26—C24 | −179.6 (4) |
C17—N29—C21—C1 | −46.3 (6) | O28—C12—C26—C14 | −179.6 (4) |
C21—C1—C7—C13 | 29.4 (4) | O18—C12—C26—C14 | −1.1 (7) |
C7—C1—C21—O31 | −22.1 (4) | O28—C12—C26—C24 | 1.9 (6) |
C21—C1—C7—O28 | 143.8 (4) | C5—C14—C26—C12 | −179.5 (4) |
C7—C1—C21—N29 | 97.1 (4) | C5—C14—C26—C24 | −0.9 (7) |
C16—C2—C24—C26 | 0.2 (7) | C9—C15—C20—C8 | 179.1 (4) |
C24—C2—C16—C11 | 179.7 (4) | C9—C15—C20—C4 | −1.8 (7) |
C24—C2—C16—C5 | −1.1 (7) | N29—C17—C25—N23 | −0.8 (5) |
O30—C3—C13—O31 | −67.2 (4) | C2—C24—C26—C14 | 0.8 (7) |
O30—C3—C13—C7 | 52.4 (5) | C2—C24—C26—C12 | 179.3 (4) |
Experimental details
Crystal data | |
Chemical formula | C24H24N2O5 |
Mr | 420.45 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 103 |
a, b, c (Å) | 14.436 (3), 5.3850 (11), 15.061 (3) |
β (°) | 116.25 (3) |
V (Å3) | 1050.1 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.1 × 0.1 × 0.1 |
Data collection | |
Diffractometer | Bruker–Nonius Kappa CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12891, 2647, 1726 |
Rint | 0.097 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.137, 1.01 |
No. of reflections | 2647 |
No. of parameters | 280 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.28, −0.34 |
Computer programs: KappaCCD (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), DENZO and SCALEPACK, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990).
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In the course of our studies regarding the use of artificial azole nucleosides (azole = imidazole, 1,2,4-triazole, tetrazole) in metal-ion mediated base pairs (Böhme et al., 2007; Müller et al., 2007; Polonius & Müller, 2007; Müller et al., 2005) we have isolated the title compound (Figure 1) as a reaction intermediate in the synthesis of imidazole nucleoside. It crystallizes in the same space group and with very similar unit-cell dimensions as the related triazole nucleoside (Müller et al., 2005). All bond lengths and angles are within the normal range (Allen et al., 1987). The artificial nucleobase is connected to the sugar moiety via an N-glycosidic bond. It is oriented anti with respect to the sugar. The deoxyribose adopts a C3'-endo conformation (phase angle of pseudorotation = 7.7 (5)°). The title compound forms long columns along the crystallographic b axis (Fig. 2). However, there is no π stacking between neighboring toluoyl rings that are related by the symmetry operator (x, y + 1, z). Instead, neighboring rings that are related by the symmetry operator (1 - x, y + 1/2, 3 - z) are oriented at an angle of 62.7 (2)° with respect to each other.