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The crystal structure of the title compound, C16H16FNO, was determined as part of a study of the biological activity of pyridine-substituted cyclo­pentene derivatives as p38 mitogen-activated protein kinase (MAPK) inhibitors. The 4-fluoro­phenyl and 4-pyridyl rings are trans positioned with respect to each other. The compound exists as a racemic mixture. The synthesis was achieved via direct inter­action between the reactive complex Grignard reagent PyMgCl·LiCl and the enolizable ketone 4-fluoro­phenyl­cyclo­penta­none with the assistance of the neodymium salt catalyst NdCl3·2LiCl. The crystal packing is characterized by zigzag chains of mol­ecules, which are connected by O—H...N hydrogen bonds running along the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034034/bt2433sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034034/bt2433Isup2.hkl
Contains datablock I

CCDC reference: 657791

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.125
  • wR factor = 0.361
  • Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level B RFACR01_ALERT_3_B The value of the weighted R factor is > 0.35 Weighted R factor given 0.361 PLAT031_ALERT_4_B Refined Extinction Parameter within Range ...... 1.50 Sigma PLAT084_ALERT_2_B High R2 Value .................................. 0.36
Alert level C ABSTM02_ALERT_3_C The ratio of Tmax/Tmin expected RT(exp) is > 1.10 Absorption corrections should be applied. Tmin and Tmax expected: 0.831 0.957 RT(exp) = 1.152 DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.693 Test value = 0.675 DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. RFACG01_ALERT_3_C The value of the R factor is > 0.10 R factor given 0.125 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc. PLAT057_ALERT_3_C Correction for Absorption Required RT(exp) ... 1.19 PLAT082_ALERT_2_C High R1 Value .................................. 0.13 PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.69 e/A    PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.04 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 10
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C1 = ... S PLAT793_ALERT_1_G Check the Absolute Configuration of C2 = ... S
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 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

Comment top

Compound 4 was prepared in the course of our study on cyclopentene derivatives bearing the typical vicinal 4-pyridyl and 4-fluorophenyl pharmacophores of MAP Kinase inhibitors. Pyridinylimidazoles are described in the literature as inhibitors for p38 MAP Kinase (Wagner et al., 2006; Kaminska, 2005). The prototypical pyridinylimidazole SB 203580 is one of the best studied p38 inhibitors reported until now. Figure 1 shows the most important interactions between the ATP binding sites of p38 kinase and the imidazole inhibitor SB203580 (Wang et al., 1998; Laufer et al., 2006). The 4-fluorophenyl ring of SB203580 occupies a hydrophobic back pocket gaining selectivity. Vicinal to this interaction site, 4-pyridinyl moiety forms a hydrogen bond from the backbone NH group of Met 109 of p38 MAP Kinase (Fig. 1).

Meanwhile, the importance of a further hydrogen bond between N3 of the imidazole core and Lys53 of p38 MAP Kinase, as shown in figure 1, is not yet clear and the speculation about its significance is not settled. Based on this concept, replacement of imidazole core by a cyclopentene ring would require the preparation of 2-fluorophenyl-1-pyridinyl cyclopentanol 4 as a key compound for such comparative bioassay study. Going from the data obtained from the X-ray structure of compound 4 (Figs. 2 and 3), it is impossible for the vicinal 4-fluorophenyl and 4-pyridinyl groups (due to their location in trans position to each other) to exert their expected functions with p38 MAPK as described above in case of SB203580 inhibitor (Fig. 1).

So, the loss of the biological activity of compound 4 can not be attributed just to the absence of the nitrogen atoms in the cyclopentane core itself. Accordingly, and based on this result, we plan to prepare cyclopentene derivatives which have vicinal 4-fluorophenyl and 4-pyridinyl groups in cis orientation in order to get more accurate and comparable information about the extent of the importance of the hydrogen bond between N3 of the imidazole core and Lys 53 of P38 MAP Kinase in terms of its biological activity.

Related literature top

In the title compound the vicinal substituents are in a trans position with respect to each other; this is different to the structure of other related five-membered rings, as exemplified by the pyridinylimidazole SB203580 inhibitor for p38 MAPK (Wang et al., 1998; Laufer et al., 2006). For further literature, see Abu Thaher et al. (2007, and references therein).

For related literature, see: Kaminska (2005); Krasovskiy & Knochel (2004); Krasovskiy et al. (2006); Wagner & Laufer (2006).

Experimental top

Compound 4 was obtained by reacting 1.0 mmol of 2-(4-fluorophenyl)-1-cyclopentanone 3 to 1.05 mmol N dC l3.2LiCl (Krasovskiy et al., 2006) under dry conditions, followed by adding the prepared complex Grignard PyMgCl.LiCl, from iPrMgCl.LiCl by exchange reaction (Krasovskiy and Knochel, 2004), to the first reaction at 273 K and then at rt for 8–10 h. When the reaction was completed, saturated aqueous NH4Cl (2 ml) and water (10 ml) were added. The aqueous layer was extracted with diethyl ether (4 x 10 ml), and the combined organic extracts were dried (Na2SO4) and evaporated to dryness. The crude product was purified by flash column chromatography (n-hexane / ethyl acetate, 3:1, v/v) giving 4 (yield 58.5°) as colorless, crystalline needles. For X-ray analysis suitable crystals of compund 4 were obtained by slow evaporation at 298 K of methanol - chloroform (2:1) solution.

Refinement top

Hydrogen atoms attached to carbons were placed at calculated positions with C—H=0.95A% (aromatic) or 0.99–1.00 Å (sp3 C-atom). Hydrogen atom attached to O6 was located in a difference Fourier map. The isotropic displacement parameters were set to 1.2–1.5 times of the Ueq of the parent atom.

Structure description top

Compound 4 was prepared in the course of our study on cyclopentene derivatives bearing the typical vicinal 4-pyridyl and 4-fluorophenyl pharmacophores of MAP Kinase inhibitors. Pyridinylimidazoles are described in the literature as inhibitors for p38 MAP Kinase (Wagner et al., 2006; Kaminska, 2005). The prototypical pyridinylimidazole SB 203580 is one of the best studied p38 inhibitors reported until now. Figure 1 shows the most important interactions between the ATP binding sites of p38 kinase and the imidazole inhibitor SB203580 (Wang et al., 1998; Laufer et al., 2006). The 4-fluorophenyl ring of SB203580 occupies a hydrophobic back pocket gaining selectivity. Vicinal to this interaction site, 4-pyridinyl moiety forms a hydrogen bond from the backbone NH group of Met 109 of p38 MAP Kinase (Fig. 1).

Meanwhile, the importance of a further hydrogen bond between N3 of the imidazole core and Lys53 of p38 MAP Kinase, as shown in figure 1, is not yet clear and the speculation about its significance is not settled. Based on this concept, replacement of imidazole core by a cyclopentene ring would require the preparation of 2-fluorophenyl-1-pyridinyl cyclopentanol 4 as a key compound for such comparative bioassay study. Going from the data obtained from the X-ray structure of compound 4 (Figs. 2 and 3), it is impossible for the vicinal 4-fluorophenyl and 4-pyridinyl groups (due to their location in trans position to each other) to exert their expected functions with p38 MAPK as described above in case of SB203580 inhibitor (Fig. 1).

So, the loss of the biological activity of compound 4 can not be attributed just to the absence of the nitrogen atoms in the cyclopentane core itself. Accordingly, and based on this result, we plan to prepare cyclopentene derivatives which have vicinal 4-fluorophenyl and 4-pyridinyl groups in cis orientation in order to get more accurate and comparable information about the extent of the importance of the hydrogen bond between N3 of the imidazole core and Lys 53 of P38 MAP Kinase in terms of its biological activity.

In the title compound the vicinal substituents are in a trans position with respect to each other; this is different to the structure of other related five-membered rings, as exemplified by the pyridinylimidazole SB203580 inhibitor for p38 MAPK (Wang et al., 1998; Laufer et al., 2006). For further literature, see Abu Thaher et al. (2007, and references therein).

For related literature, see: Kaminska (2005); Krasovskiy & Knochel (2004); Krasovskiy et al. (2006); Wagner & Laufer (2006).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. Schematic drawing of important interactions between the prototypical pyridin-4-yl imidazole inhibitor SB 203580 and the ATP binding site of p38.
[Figure 2] Fig. 2. The molecular structure of 4. Dislacement ellipsoids are drawn at the 50% probability level and H atoms are depicted as circles of arbitrary radius.
[Figure 3] Fig. 3. Part of the packing of 4, viewed along the b axis showing the racemic modification of the molecule. H atoms are omitted. The packing is influenced by O—H···N hydrogen bonds along the b axis.
[Figure 4] Fig. 4. Chemical preparation of 4. Reagents and conditions: (i) 4-fluorophenylmagnesiumbromide, ether, reflux; (ii) H2O2, formic acid; (iii) NdCl3.2LiCl, 1 h and then 2 equivalents PyMgCl.LiCl, 273 K, 8–10 h.
2-(4-Fluorophenyl)-1-(4-pyridyl)cyclopentan-1-ol top
Crystal data top
C16H16FNOF(000) = 544
Mr = 257.30Dx = 1.278 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 11.7228 (8) Åθ = 20–25.7°
b = 13.6606 (8) ŵ = 0.73 mm1
c = 8.6194 (11) ÅT = 193 K
β = 104.366 (10)°Plate, colourless
V = 1337.2 (2) Å30.30 × 0.30 × 0.06 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.050
Radiation source: rotating anodeθmax = 70.3°, θmin = 3.9°
Graphite monochromatorh = 1413
ω/2θ scansk = 016
2701 measured reflectionsl = 010
2523 independent reflections3 standard reflections every 60 min
1235 reflections with I > 2σ(I) intensity decay: 5%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.126H-atom parameters constrained
wR(F2) = 0.361 [1 + -exp(-4.00(sinθ/λ)2)]/[σ2(Fo2) + (0.08P)2 + sinθ/λ],
where P = 0.33333Fo2 + 0.66667Fc2
S = 1.28(Δ/σ)max < 0.001
2523 reflectionsΔρmax = 0.69 e Å3
173 parametersΔρmin = 0.67 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.006 (4)
Crystal data top
C16H16FNOV = 1337.2 (2) Å3
Mr = 257.30Z = 4
Monoclinic, P21/cCu Kα radiation
a = 11.7228 (8) ŵ = 0.73 mm1
b = 13.6606 (8) ÅT = 193 K
c = 8.6194 (11) Å0.30 × 0.30 × 0.06 mm
β = 104.366 (10)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.050
2701 measured reflections3 standard reflections every 60 min
2523 independent reflections intensity decay: 5%
1235 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.1260 restraints
wR(F2) = 0.361H-atom parameters constrained
S = 1.28Δρmax = 0.69 e Å3
2523 reflectionsΔρmin = 0.67 e Å3
173 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
C10.1840 (6)0.4649 (4)0.8347 (8)0.0455 (17)
C20.3152 (6)0.4837 (4)0.8462 (8)0.0469 (17)
H20.34330.53340.93230.056*
C30.3736 (7)0.3850 (5)0.9078 (10)0.060 (2)
H3A0.37410.34050.81730.072*
H3B0.45560.39510.97090.072*
C40.2981 (8)0.3433 (5)1.0124 (11)0.064 (2)
H4A0.34290.34281.12600.077*
H4B0.27470.27520.97980.077*
C50.1886 (7)0.4085 (4)0.9909 (9)0.0553 (19)
H5A0.19660.45401.08240.066*
H5B0.11680.36840.98120.066*
O60.1394 (4)0.4049 (3)0.6997 (5)0.0528 (13)
H60.10840.35470.72820.079*
C70.1137 (6)0.5605 (4)0.8200 (9)0.0463 (17)
C80.0127 (6)0.5733 (5)0.6989 (10)0.0525 (18)
H80.01700.52170.62630.063*
C90.0443 (8)0.6628 (5)0.6854 (10)0.061 (2)
H90.11240.67090.59970.074*
N100.0107 (6)0.7380 (4)0.7833 (9)0.0617 (18)
C110.0856 (7)0.7239 (5)0.9014 (11)0.061 (2)
H110.11280.77640.97340.073*
C120.1476 (7)0.6374 (4)0.9246 (10)0.0550 (19)
H120.21410.63081.01310.066*
C130.3400 (6)0.5238 (4)0.6929 (9)0.0465 (16)
C140.3684 (7)0.6227 (5)0.6829 (10)0.0548 (19)
H140.37390.66350.77370.066*
C150.3884 (7)0.6625 (5)0.5464 (10)0.061 (2)
H150.40860.72970.54250.073*
C160.3788 (7)0.6039 (5)0.4171 (10)0.063 (2)
C170.3516 (7)0.5067 (5)0.4207 (10)0.061 (2)
H170.34540.46700.32850.074*
C180.3332 (6)0.4667 (5)0.5597 (9)0.0558 (19)
H180.31570.39900.56320.067*
F190.3971 (5)0.6414 (3)0.2785 (6)0.0785 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.073 (4)0.021 (2)0.050 (4)0.004 (2)0.030 (4)0.008 (2)
C20.057 (4)0.028 (2)0.058 (4)0.002 (2)0.018 (3)0.007 (3)
C30.066 (5)0.038 (3)0.077 (5)0.009 (3)0.021 (4)0.003 (3)
C40.088 (6)0.036 (3)0.069 (5)0.006 (3)0.023 (4)0.011 (3)
C50.084 (5)0.030 (3)0.059 (4)0.006 (3)0.031 (4)0.003 (3)
O60.082 (3)0.0270 (18)0.056 (3)0.010 (2)0.030 (3)0.0010 (18)
C70.047 (4)0.033 (3)0.067 (5)0.000 (2)0.030 (4)0.001 (3)
C80.048 (4)0.043 (3)0.071 (5)0.001 (3)0.022 (4)0.006 (3)
C90.074 (5)0.054 (4)0.063 (5)0.012 (3)0.030 (4)0.003 (4)
N100.071 (5)0.045 (3)0.077 (5)0.014 (3)0.036 (4)0.005 (3)
C110.061 (5)0.041 (3)0.086 (6)0.009 (3)0.028 (5)0.013 (4)
C120.068 (5)0.035 (3)0.069 (5)0.005 (3)0.029 (4)0.000 (3)
C130.051 (4)0.030 (3)0.065 (4)0.004 (2)0.026 (3)0.002 (3)
C140.066 (5)0.039 (3)0.065 (5)0.003 (3)0.026 (4)0.001 (3)
C150.079 (5)0.038 (3)0.076 (6)0.004 (3)0.036 (4)0.007 (3)
C160.075 (5)0.048 (4)0.077 (6)0.010 (3)0.040 (5)0.023 (4)
C170.072 (5)0.056 (4)0.061 (5)0.004 (3)0.026 (4)0.012 (4)
C180.065 (5)0.037 (3)0.073 (5)0.006 (3)0.029 (4)0.002 (3)
F190.111 (4)0.066 (3)0.070 (3)0.008 (2)0.044 (3)0.022 (2)
Geometric parameters (Å, º) top
C1—O61.413 (7)C8—H80.9500
C1—C71.533 (8)C9—N101.326 (10)
C1—C21.538 (9)C9—H90.9500
C1—C51.541 (9)N10—C111.333 (11)
C2—C131.523 (9)C11—C121.375 (9)
C2—C31.545 (9)C11—H110.9500
C2—H21.0000C12—H120.9500
C3—C41.522 (10)C13—C181.374 (9)
C3—H3A0.9900C13—C141.400 (9)
C3—H3B0.9900C14—C151.368 (10)
C4—C51.536 (11)C14—H140.9500
C4—H4A0.9900C15—C161.354 (11)
C4—H4B0.9900C15—H150.9500
C5—H5A0.9900C16—F191.365 (8)
C5—H5B0.9900C16—C171.368 (10)
O6—H60.8400C17—C181.381 (10)
C7—C121.377 (9)C17—H170.9500
C7—C81.382 (10)C18—H180.9500
C8—C91.384 (10)
O6—C1—C7110.2 (6)C8—C7—C1120.8 (6)
O6—C1—C2108.0 (5)C7—C8—C9118.7 (7)
C7—C1—C2111.8 (4)C7—C8—H8120.6
O6—C1—C5110.8 (4)C9—C8—H8120.6
C7—C1—C5113.6 (5)N10—C9—C8124.7 (9)
C2—C1—C5102.1 (6)N10—C9—H9117.6
C13—C2—C1114.0 (6)C8—C9—H9117.6
C13—C2—C3116.6 (5)C9—N10—C11115.8 (6)
C1—C2—C3103.1 (5)N10—C11—C12123.5 (7)
C13—C2—H2107.5N10—C11—H11118.2
C1—C2—H2107.5C12—C11—H11118.2
C3—C2—H2107.5C11—C12—C7120.2 (8)
C4—C3—C2104.9 (6)C11—C12—H12119.9
C4—C3—H3A110.8C7—C12—H12119.9
C2—C3—H3A110.8C18—C13—C14117.5 (6)
C4—C3—H3B110.8C18—C13—C2122.5 (5)
C2—C3—H3B110.8C14—C13—C2120.0 (6)
H3A—C3—H3B108.8C15—C14—C13122.1 (7)
C3—C4—C5107.6 (6)C15—C14—H14119.0
C3—C4—H4A110.2C13—C14—H14119.0
C5—C4—H4A110.2C16—C15—C14118.4 (6)
C3—C4—H4B110.2C16—C15—H15120.8
C5—C4—H4B110.2C14—C15—H15120.8
H4A—C4—H4B108.5C15—C16—F19120.0 (6)
C4—C5—C1104.0 (5)C15—C16—C17121.8 (7)
C4—C5—H5A110.9F19—C16—C17118.2 (7)
C1—C5—H5A110.9C16—C17—C18119.4 (7)
C4—C5—H5B110.9C16—C17—H17120.3
C1—C5—H5B110.9C18—C17—H17120.3
H5A—C5—H5B109.0C13—C18—C17120.8 (6)
C1—O6—H6109.3C13—C18—H18119.6
C12—C7—C8116.9 (6)C17—C18—H18119.6
C12—C7—C1122.3 (7)
O6—C1—C2—C1353.2 (6)C7—C8—C9—N101.7 (11)
C7—C1—C2—C1368.2 (7)C8—C9—N10—C110.4 (11)
C5—C1—C2—C13170.0 (5)C9—N10—C11—C120.6 (11)
O6—C1—C2—C374.2 (6)N10—C11—C12—C72.2 (11)
C7—C1—C2—C3164.4 (6)C8—C7—C12—C113.3 (9)
C5—C1—C2—C342.6 (6)C1—C7—C12—C11176.3 (6)
C13—C2—C3—C4157.3 (6)C1—C2—C13—C1873.7 (7)
C1—C2—C3—C431.6 (7)C3—C2—C13—C1846.4 (9)
C2—C3—C4—C58.3 (9)C1—C2—C13—C14104.9 (7)
C3—C4—C5—C118.1 (8)C3—C2—C13—C14135.0 (7)
O6—C1—C5—C477.5 (7)C18—C13—C14—C150.3 (11)
C7—C1—C5—C4157.8 (6)C2—C13—C14—C15178.3 (7)
C2—C1—C5—C437.3 (6)C13—C14—C15—C160.8 (12)
O6—C1—C7—C12171.5 (5)C14—C15—C16—F19179.4 (7)
C2—C1—C7—C1251.4 (8)C14—C15—C16—C171.0 (12)
C5—C1—C7—C1263.5 (8)C15—C16—C17—C180.0 (12)
O6—C1—C7—C88.0 (7)F19—C16—C17—C18179.7 (7)
C2—C1—C7—C8128.2 (6)C14—C13—C18—C171.3 (11)
C5—C1—C7—C8116.9 (7)C2—C13—C18—C17177.3 (7)
C12—C7—C8—C93.0 (9)C16—C17—C18—C131.1 (11)
C1—C7—C8—C9176.6 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6···N10i0.841.952.758 (7)161
Symmetry code: (i) x, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC16H16FNO
Mr257.30
Crystal system, space groupMonoclinic, P21/c
Temperature (K)193
a, b, c (Å)11.7228 (8), 13.6606 (8), 8.6194 (11)
β (°) 104.366 (10)
V3)1337.2 (2)
Z4
Radiation typeCu Kα
µ (mm1)0.73
Crystal size (mm)0.30 × 0.30 × 0.06
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
2701, 2523, 1235
Rint0.050
(sin θ/λ)max1)0.611
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.126, 0.361, 1.28
No. of reflections2523
No. of parameters173
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.69, 0.67

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), CAD-4 Software, CORINC (Dräger & Gattow, 1971), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6···N10i0.841.952.758 (7)160.5
Symmetry code: (i) x, y1/2, z+3/2.
 

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