


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810025572/bt5280sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810025572/bt5280Isup2.hkl |
CCDC reference: 788358
Key indicators
- Single-crystal X-ray study
- T = 296 K, P = 0.0 kPa
- Mean
(C-C) = 0.003 Å
- R factor = 0.056
- wR factor = 0.154
- Data-to-parameter ratio = 15.7
checkCIF/PLATON results
No syntax errors found
Alert level C DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.680 Test value = 0.600 DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT097_ALERT_2_C Large Reported Max. (Positive) Residual Density 0.68 eA-3 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.17 Ratio PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C7 - C8 ... 1.42 Ang. PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 3
Alert level G PLAT793_ALERT_4_G The Model has Chirality at C1 (Verify) .... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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
To a solution of the diethyl (4-methoxybenzyl)propanedioate (5 mmol) in water (20 ml) was added the 3,5-dimethyl-1H-pyrazole (6 mmol) and the mixture and the stirring was continued at room temperature until the complete consume of the starting material. After removing solvent, the crude products were dissolved in diethyl ether (2x40 ml) and washed with water until the pH became neutral. The organic solvent was dried with sodium sulfate and then evaporated to give the pure compound (I) with 76% yield.. White crystals are obtained by recrystallization in ether/hexane (2/1).
Suitable single-crystal of malonate derivative (I) was obtained by recrystallization from ethanol. A white-transparent crystal was mounted on a glass fibre.
All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 0.96 Å (methyl), C—H = 0.93 Å (aromatic), 0.97 Å (methylene) and 0.98 Å (methine) with Uiso(H) = 1.2Ueq or Uiso(H) = 1.5Ueq(methyl).
For the rational design of new HIV-1 Integrase (H—I) inhibitors, one validated target for chemotherapeutic intervention (Dayam et al., 2007), is fundamentally based on intermolecular coordination between H—I / chemical inhibitor / metals (Mg+2 and Mn+2, co-factors of the enzyme), leading to the formation of bimetallic complexes (Zeng et al., 2008; Sechi et al., 2009). Thereby, several bimetallic metal complexes, in many cases exploring the known-well polydentate ligands, appear in this scenario as the most promising concept to be employed in either enzyme / drug interaction or electron transfer process, in the last case involving the biological oxygen transfer (Sechi et al., 2009; Ramkumar et al., 2008). Another exciting example of application for such polydentate ligands involves the synergic water activation, that occurs via the so-called -remote metallic atoms. Such organometallic compounds are structurally deemed to promote or block the H—I activity (Zeng et al., 2008).
In the molecule of the title compound (Fig.1), the dihedral angle between the planes of the pheny and the pyrazol ring is 83.96 (10)°.
For related compounds displaying biological activity, see: Dayam et al. (2007); Patil et al. (2007); Ramkumar et al. (2008); Sechi et al. (2009) & Zeng et al. (2008). For the synthetic procedure, see: Pommier & Neamati (2006).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).
C20H26N2O5 | F(000) = 800 |
Mr = 374.43 | Dx = 1.243 Mg m−3 |
Monoclinic, P21/c | Melting point: 361 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 11.9618 (3) Å | Cell parameters from 2174 reflections |
b = 7.9681 (2) Å | θ = 2.3–27.1° |
c = 21.1269 (6) Å | µ = 0.09 mm−1 |
β = 96.504 (1)° | T = 296 K |
V = 2000.70 (9) Å3 | Block, colourless |
Z = 4 | 0.23 × 0.17 × 0.14 mm |
Bruker X8 APEXII CCD area-detector diffractometer | 3177 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.027 |
Graphite monochromator | θmax = 26.0°, θmin = 2.7° |
φ and ω scans | h = −14→14 |
18616 measured reflections | k = −9→9 |
3921 independent reflections | l = −26→26 |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.154 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0687P)2 + 1.8319P] where P = (Fo2 + 2Fc2)/3 |
3921 reflections | (Δ/σ)max = 0.007 |
249 parameters | Δρmax = 0.68 e Å−3 |
0 restraints | Δρmin = −0.45 e Å−3 |
C20H26N2O5 | V = 2000.70 (9) Å3 |
Mr = 374.43 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.9618 (3) Å | µ = 0.09 mm−1 |
b = 7.9681 (2) Å | T = 296 K |
c = 21.1269 (6) Å | 0.23 × 0.17 × 0.14 mm |
β = 96.504 (1)° |
Bruker X8 APEXII CCD area-detector diffractometer | 3177 reflections with I > 2σ(I) |
18616 measured reflections | Rint = 0.027 |
3921 independent reflections |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.154 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.68 e Å−3 |
3921 reflections | Δρmin = −0.45 e Å−3 |
249 parameters |
Experimental. The data collection nominally covered a sphere of reciprocal space, by a combination of tree sets of exposures; each set had a different φ angle for the crystal and each exposure covered 0.5° in ω and 20 s in time. The crystal-to-detector distance was 37.5 mm. |
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 | ||
O2 | 0.40914 (11) | −0.14261 (19) | 0.44322 (7) | 0.0301 (3) | |
O3 | 0.26937 (12) | −0.19794 (18) | 0.36564 (7) | 0.0321 (4) | |
O4 | 0.39768 (14) | 0.2442 (2) | 0.36381 (8) | 0.0441 (4) | |
O5 | 0.23951 (15) | 0.1580 (2) | 0.30637 (7) | 0.0446 (4) | |
O1 | 0.16987 (15) | −0.2065 (2) | 0.68944 (8) | 0.0468 (5) | |
N1 | 0.25069 (14) | 0.3219 (2) | 0.47437 (8) | 0.0252 (4) | |
N2 | 0.15274 (14) | 0.3525 (2) | 0.43620 (8) | 0.0297 (4) | |
C1 | 0.29918 (16) | 0.1528 (2) | 0.47752 (9) | 0.0230 (4) | |
H1 | 0.3813 | 0.1633 | 0.4845 | 0.028* | |
C2 | 0.26772 (16) | 0.0673 (3) | 0.41296 (9) | 0.0244 (4) | |
H2 | 0.1859 | 0.0541 | 0.4051 | 0.029* | |
C11 | 0.26097 (16) | 0.0542 (2) | 0.53261 (9) | 0.0229 (4) | |
C3 | 0.32439 (16) | −0.1032 (2) | 0.41081 (9) | 0.0239 (4) | |
C12 | 0.33950 (17) | −0.0251 (3) | 0.57616 (9) | 0.0277 (4) | |
H12 | 0.4154 | −0.0197 | 0.5706 | 0.033* | |
C21 | 0.28468 (17) | 0.4563 (3) | 0.51094 (10) | 0.0285 (5) | |
C16 | 0.14790 (16) | 0.0419 (3) | 0.54174 (10) | 0.0277 (4) | |
H16 | 0.0941 | 0.0929 | 0.5127 | 0.033* | |
C13 | 0.30680 (18) | −0.1116 (3) | 0.62736 (10) | 0.0323 (5) | |
H13 | 0.3605 | −0.1643 | 0.6559 | 0.039* | |
C14 | 0.19347 (18) | −0.1206 (3) | 0.63658 (10) | 0.0311 (5) | |
C15 | 0.11364 (17) | −0.0445 (3) | 0.59307 (10) | 0.0312 (5) | |
H15 | 0.0376 | −0.0515 | 0.5983 | 0.037* | |
C6 | 0.30985 (19) | 0.1697 (3) | 0.35912 (10) | 0.0308 (5) | |
C23 | 0.12710 (18) | 0.5105 (3) | 0.44907 (11) | 0.0322 (5) | |
C4 | 0.32363 (19) | −0.3556 (3) | 0.35159 (12) | 0.0370 (5) | |
H4A | 0.2679 | −0.4329 | 0.3314 | 0.044* | |
H4B | 0.3575 | −0.4063 | 0.3909 | 0.044* | |
C22 | 0.20634 (18) | 0.5797 (3) | 0.49546 (10) | 0.0330 (5) | |
H22 | 0.2060 | 0.6874 | 0.5124 | 0.040* | |
C5 | 0.4121 (2) | −0.3243 (4) | 0.30837 (11) | 0.0466 (6) | |
H5A | 0.3789 | −0.2693 | 0.2704 | 0.070* | |
H5B | 0.4442 | −0.4292 | 0.2973 | 0.070* | |
H5C | 0.4699 | −0.2542 | 0.3296 | 0.070* | |
C25 | 0.3888 (2) | 0.4563 (3) | 0.55689 (12) | 0.0416 (6) | |
H25A | 0.3743 | 0.4000 | 0.5953 | 0.062* | |
H25B | 0.4114 | 0.5699 | 0.5666 | 0.062* | |
H25C | 0.4478 | 0.3990 | 0.5384 | 0.062* | |
C7 | 0.2781 (3) | 0.2351 (4) | 0.24975 (12) | 0.0612 (8) | |
H7A | 0.2695 | 0.3560 | 0.2515 | 0.073* | |
H7B | 0.3571 | 0.2098 | 0.2481 | 0.073* | |
C24 | 0.0258 (2) | 0.5924 (3) | 0.41410 (14) | 0.0489 (7) | |
H24A | 0.0493 | 0.6722 | 0.3842 | 0.073* | |
H24B | −0.0160 | 0.6490 | 0.4439 | 0.073* | |
H24C | −0.0209 | 0.5086 | 0.3917 | 0.073* | |
C17 | 0.0566 (2) | −0.2040 (4) | 0.70479 (13) | 0.0545 (7) | |
H17A | 0.0335 | −0.0900 | 0.7101 | 0.082* | |
H17B | 0.0521 | −0.2649 | 0.7436 | 0.082* | |
H17C | 0.0081 | −0.2554 | 0.6709 | 0.082* | |
C8 | 0.2127 (3) | 0.1700 (5) | 0.19471 (13) | 0.0731 (10) | |
H8A | 0.2245 | 0.0511 | 0.1922 | 0.110* | |
H8B | 0.2351 | 0.2230 | 0.1573 | 0.110* | |
H8C | 0.1345 | 0.1919 | 0.1975 | 0.110* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.0249 (7) | 0.0292 (8) | 0.0357 (8) | 0.0049 (6) | 0.0007 (6) | −0.0048 (6) |
O3 | 0.0317 (8) | 0.0265 (8) | 0.0371 (8) | 0.0009 (6) | −0.0005 (6) | −0.0089 (6) |
O4 | 0.0466 (10) | 0.0436 (10) | 0.0435 (9) | −0.0125 (8) | 0.0117 (8) | 0.0046 (8) |
O5 | 0.0624 (11) | 0.0441 (10) | 0.0264 (8) | −0.0085 (8) | 0.0010 (7) | 0.0036 (7) |
O1 | 0.0475 (10) | 0.0586 (12) | 0.0360 (9) | −0.0031 (9) | 0.0117 (7) | 0.0143 (8) |
N1 | 0.0258 (8) | 0.0229 (9) | 0.0265 (8) | 0.0027 (7) | 0.0013 (7) | −0.0005 (7) |
N2 | 0.0280 (9) | 0.0278 (9) | 0.0330 (9) | 0.0061 (7) | 0.0015 (7) | 0.0008 (7) |
C1 | 0.0216 (9) | 0.0196 (9) | 0.0277 (10) | 0.0025 (7) | 0.0022 (7) | −0.0011 (8) |
C2 | 0.0221 (9) | 0.0238 (10) | 0.0273 (10) | 0.0019 (8) | 0.0031 (8) | −0.0012 (8) |
C11 | 0.0242 (9) | 0.0203 (10) | 0.0246 (9) | 0.0011 (8) | 0.0036 (7) | −0.0037 (7) |
C3 | 0.0230 (10) | 0.0237 (10) | 0.0257 (9) | −0.0028 (8) | 0.0067 (8) | −0.0018 (8) |
C12 | 0.0228 (10) | 0.0311 (11) | 0.0287 (10) | 0.0005 (8) | 0.0009 (8) | −0.0014 (8) |
C21 | 0.0320 (11) | 0.0253 (11) | 0.0294 (10) | −0.0012 (8) | 0.0088 (8) | −0.0025 (8) |
C16 | 0.0242 (10) | 0.0293 (11) | 0.0292 (10) | 0.0060 (8) | 0.0014 (8) | −0.0008 (8) |
C13 | 0.0315 (11) | 0.0372 (13) | 0.0268 (10) | 0.0019 (9) | −0.0022 (8) | 0.0033 (9) |
C14 | 0.0379 (12) | 0.0310 (12) | 0.0253 (10) | −0.0017 (9) | 0.0073 (9) | 0.0011 (8) |
C15 | 0.0255 (10) | 0.0350 (12) | 0.0340 (11) | 0.0006 (9) | 0.0078 (8) | −0.0019 (9) |
C6 | 0.0405 (12) | 0.0244 (11) | 0.0277 (10) | 0.0041 (9) | 0.0041 (9) | −0.0028 (8) |
C23 | 0.0340 (11) | 0.0253 (11) | 0.0385 (11) | 0.0075 (9) | 0.0100 (9) | 0.0030 (9) |
C4 | 0.0369 (12) | 0.0279 (11) | 0.0454 (13) | 0.0010 (9) | 0.0015 (10) | −0.0159 (10) |
C22 | 0.0401 (12) | 0.0222 (10) | 0.0384 (12) | 0.0037 (9) | 0.0122 (10) | −0.0033 (9) |
C5 | 0.0504 (15) | 0.0548 (16) | 0.0350 (12) | 0.0052 (12) | 0.0069 (11) | −0.0127 (12) |
C25 | 0.0425 (13) | 0.0381 (13) | 0.0423 (13) | −0.0001 (11) | −0.0034 (10) | −0.0091 (11) |
C7 | 0.097 (2) | 0.0572 (18) | 0.0293 (13) | −0.0235 (17) | 0.0078 (14) | 0.0054 (12) |
C24 | 0.0432 (14) | 0.0413 (15) | 0.0613 (16) | 0.0180 (11) | 0.0019 (12) | 0.0046 (13) |
C17 | 0.0596 (17) | 0.0595 (18) | 0.0492 (15) | −0.0086 (14) | 0.0274 (13) | 0.0059 (13) |
C8 | 0.113 (3) | 0.072 (2) | 0.0346 (14) | −0.033 (2) | 0.0104 (16) | −0.0004 (14) |
O2—C3 | 1.199 (2) | C13—H13 | 0.9300 |
O3—C3 | 1.331 (2) | C14—C15 | 1.388 (3) |
O3—C4 | 1.460 (3) | C15—H15 | 0.9300 |
O4—C6 | 1.201 (3) | C23—C22 | 1.397 (3) |
O5—C6 | 1.322 (3) | C23—C24 | 1.496 (3) |
O5—C7 | 1.465 (3) | C4—C5 | 1.495 (3) |
O1—C14 | 1.367 (3) | C4—H4A | 0.9700 |
O1—C17 | 1.428 (3) | C4—H4B | 0.9700 |
N1—C21 | 1.355 (3) | C22—H22 | 0.9300 |
N1—N2 | 1.367 (2) | C5—H5A | 0.9600 |
N1—C1 | 1.466 (2) | C5—H5B | 0.9600 |
N2—C23 | 1.331 (3) | C5—H5C | 0.9600 |
C1—C11 | 1.517 (3) | C25—H25A | 0.9600 |
C1—C2 | 1.533 (3) | C25—H25B | 0.9600 |
C1—H1 | 0.9800 | C25—H25C | 0.9600 |
C2—C3 | 1.521 (3) | C7—C8 | 1.424 (4) |
C2—C6 | 1.531 (3) | C7—H7A | 0.9700 |
C2—H2 | 0.9800 | C7—H7B | 0.9700 |
C11—C12 | 1.390 (3) | C24—H24A | 0.9600 |
C11—C16 | 1.391 (3) | C24—H24B | 0.9600 |
C12—C13 | 1.376 (3) | C24—H24C | 0.9600 |
C12—H12 | 0.9300 | C17—H17A | 0.9600 |
C21—C22 | 1.372 (3) | C17—H17B | 0.9600 |
C21—C25 | 1.490 (3) | C17—H17C | 0.9600 |
C16—C15 | 1.385 (3) | C8—H8A | 0.9600 |
C16—H16 | 0.9300 | C8—H8B | 0.9600 |
C13—C14 | 1.393 (3) | C8—H8C | 0.9600 |
C3—O3—C4 | 116.03 (16) | N2—C23—C24 | 120.3 (2) |
C6—O5—C7 | 115.4 (2) | C22—C23—C24 | 128.4 (2) |
C14—O1—C17 | 117.87 (19) | O3—C4—C5 | 110.0 (2) |
C21—N1—N2 | 112.18 (17) | O3—C4—H4A | 109.7 |
C21—N1—C1 | 127.50 (16) | C5—C4—H4A | 109.7 |
N2—N1—C1 | 119.92 (16) | O3—C4—H4B | 109.7 |
C23—N2—N1 | 104.46 (17) | C5—C4—H4B | 109.7 |
N1—C1—C11 | 111.05 (15) | H4A—C4—H4B | 108.2 |
N1—C1—C2 | 108.18 (15) | C21—C22—C23 | 105.97 (19) |
C11—C1—C2 | 112.80 (16) | C21—C22—H22 | 127.0 |
N1—C1—H1 | 108.2 | C23—C22—H22 | 127.0 |
C11—C1—H1 | 108.2 | C4—C5—H5A | 109.5 |
C2—C1—H1 | 108.2 | C4—C5—H5B | 109.5 |
C3—C2—C6 | 105.57 (15) | H5A—C5—H5B | 109.5 |
C3—C2—C1 | 110.98 (16) | C4—C5—H5C | 109.5 |
C6—C2—C1 | 110.86 (16) | H5A—C5—H5C | 109.5 |
C3—C2—H2 | 109.8 | H5B—C5—H5C | 109.5 |
C6—C2—H2 | 109.8 | C21—C25—H25A | 109.5 |
C1—C2—H2 | 109.8 | C21—C25—H25B | 109.5 |
C12—C11—C16 | 118.10 (18) | H25A—C25—H25B | 109.5 |
C12—C11—C1 | 120.23 (17) | C21—C25—H25C | 109.5 |
C16—C11—C1 | 121.66 (17) | H25A—C25—H25C | 109.5 |
O2—C3—O3 | 125.32 (19) | H25B—C25—H25C | 109.5 |
O2—C3—C2 | 124.59 (18) | C8—C7—O5 | 108.6 (2) |
O3—C3—C2 | 110.01 (16) | C8—C7—H7A | 110.0 |
C13—C12—C11 | 121.13 (19) | O5—C7—H7A | 110.0 |
C13—C12—H12 | 119.4 | C8—C7—H7B | 110.0 |
C11—C12—H12 | 119.4 | O5—C7—H7B | 110.0 |
N1—C21—C22 | 106.12 (18) | H7A—C7—H7B | 108.3 |
N1—C21—C25 | 123.09 (19) | C23—C24—H24A | 109.5 |
C22—C21—C25 | 130.8 (2) | C23—C24—H24B | 109.5 |
C15—C16—C11 | 121.46 (19) | H24A—C24—H24B | 109.5 |
C15—C16—H16 | 119.3 | C23—C24—H24C | 109.5 |
C11—C16—H16 | 119.3 | H24A—C24—H24C | 109.5 |
C12—C13—C14 | 120.21 (19) | H24B—C24—H24C | 109.5 |
C12—C13—H13 | 119.9 | O1—C17—H17A | 109.5 |
C14—C13—H13 | 119.9 | O1—C17—H17B | 109.5 |
O1—C14—C15 | 124.7 (2) | H17A—C17—H17B | 109.5 |
O1—C14—C13 | 115.74 (19) | O1—C17—H17C | 109.5 |
C15—C14—C13 | 119.52 (19) | H17A—C17—H17C | 109.5 |
C16—C15—C14 | 119.56 (19) | H17B—C17—H17C | 109.5 |
C16—C15—H15 | 120.2 | C7—C8—H8A | 109.5 |
C14—C15—H15 | 120.2 | C7—C8—H8B | 109.5 |
O4—C6—O5 | 124.9 (2) | H8A—C8—H8B | 109.5 |
O4—C6—C2 | 124.10 (19) | C7—C8—H8C | 109.5 |
O5—C6—C2 | 110.92 (18) | H8A—C8—H8C | 109.5 |
N2—C23—C22 | 111.27 (19) | H8B—C8—H8C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···O2i | 0.93 | 2.51 | 3.358 (3) | 152 |
Symmetry code: (i) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C20H26N2O5 |
Mr | 374.43 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 11.9618 (3), 7.9681 (2), 21.1269 (6) |
β (°) | 96.504 (1) |
V (Å3) | 2000.70 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.23 × 0.17 × 0.14 |
Data collection | |
Diffractometer | Bruker X8 APEXII CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18616, 3921, 3177 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.154, 1.05 |
No. of reflections | 3921 |
No. of parameters | 249 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.68, −0.45 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···O2i | 0.93 | 2.51 | 3.358 (3) | 152 |
Symmetry code: (i) −x+1, −y, −z+1. |
For the rational design of new HIV-1 Integrase (H—I) inhibitors, one validated target for chemotherapeutic intervention (Dayam et al., 2007), is fundamentally based on intermolecular coordination between H—I / chemical inhibitor / metals (Mg+2 and Mn+2, co-factors of the enzyme), leading to the formation of bimetallic complexes (Zeng et al., 2008; Sechi et al., 2009). Thereby, several bimetallic metal complexes, in many cases exploring the known-well polydentate ligands, appear in this scenario as the most promising concept to be employed in either enzyme / drug interaction or electron transfer process, in the last case involving the biological oxygen transfer (Sechi et al., 2009; Ramkumar et al., 2008). Another exciting example of application for such polydentate ligands involves the synergic water activation, that occurs via the so-called -remote metallic atoms. Such organometallic compounds are structurally deemed to promote or block the H—I activity (Zeng et al., 2008).
In the molecule of the title compound (Fig.1), the dihedral angle between the planes of the pheny and the pyrazol ring is 83.96 (10)°.