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The title compound, C11H23N3O5, contains a pyrazole ring and a di­hydro­furan ring connected by an NH bridge. The pyrazole ring is planar, while the di­hydrofuran ring adopts a twist conformation. The two rings are linked by an intramolecular O—H...N hydrogen bond. In the crystal structure, the intermolecular hydrogen-bond network forms chains parallel to the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803015514/su6034sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803015514/su6034Isup2.hkl
Contains datablock I

CCDC reference: 221699

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.056
  • wR factor = 0.139
  • Data-to-parameter ratio = 13.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 1990).

1-[(2RS,3RS)-4-Acetyl-2-hydroxy-3-(5-methoxy-4-methyl-3-phenylpyrazol-1- ylamino)-2,5-dimethyl-2,3-dihydro-furan-3-yl]ethanone top
Crystal data top
C21H25N3O5F(000) = 848
Mr = 399.44Dx = 1.292 Mg m3
Monoclinic, P21/cMelting point: 387 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 11.339 (3) ÅCell parameters from 35 reflections
b = 7.444 (2) Åθ = 4–38°
c = 24.546 (4) ŵ = 0.09 mm1
β = 97.61 (1)°T = 293 K
V = 2053.6 (8) Å3Needle, colourless
Z = 40.4 × 0.2 × 0.2 mm
Data collection top
Siemens P4
diffractometer
Rint = 0.031
Radiation source: sealed tubeθmax = 25°, θmin = 1.8°
Graphite monochromatorh = 113
ω scansk = 18
4895 measured reflectionsl = 2929
3612 independent reflections3 standard reflections every 97 reflections
1988 reflections with I > 2σ(I) intensity decay: <1%
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.056 w = 1/[σ2(Fo2) + (0.059P)2 + 0.0883P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.139(Δ/σ)max = 0.011
S = 1.01Δρmax = 0.17 e Å3
3612 reflectionsΔρmin = 0.26 e Å3
276 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O40.95159 (19)0.0998 (3)0.67593 (9)0.0407 (6)
H40.89880.10480.69570.072 (14)*
O10.94465 (17)0.2075 (3)0.68887 (7)0.0401 (5)
O50.47868 (18)0.0204 (3)0.62516 (8)0.0468 (6)
N20.6771 (2)0.0180 (3)0.66575 (9)0.0339 (6)
N10.7265 (2)0.0365 (3)0.61673 (9)0.0347 (6)
H10.74830.16290.61320.040 (8)*
O20.6968 (2)0.5574 (3)0.60277 (11)0.0742 (8)
O30.8716 (2)0.1866 (4)0.52146 (9)0.0673 (8)
N30.7434 (2)0.0313 (3)0.71573 (9)0.0361 (6)
C120.5472 (3)0.0030 (4)0.72479 (12)0.0356 (7)
C30.7924 (3)0.2816 (4)0.62245 (11)0.0334 (7)
C101.0562 (3)0.0852 (5)0.62198 (13)0.0497 (9)
H10C1.06340.01290.59730.06*
H10A1.05190.19620.60190.06*
H10B1.12410.08710.64980.06*
C140.7106 (3)0.0130 (4)0.81087 (12)0.0361 (7)
C130.6651 (3)0.0187 (4)0.75161 (11)0.0347 (7)
C180.8617 (3)0.0828 (5)0.88322 (14)0.0532 (9)
H180.93320.14180.89430.056 (10)*
C110.5601 (3)0.0020 (4)0.66994 (12)0.0354 (7)
C10.9451 (3)0.0619 (4)0.64851 (11)0.0355 (7)
C50.8627 (3)0.4933 (4)0.70387 (13)0.0499 (9)
H5A0.78760.55360.69590.06*
H5B0.87540.45980.7420.06*
H5C0.92530.57230.69610.06*
C20.8231 (3)0.0914 (4)0.60870 (11)0.0332 (7)
C80.8461 (3)0.0624 (5)0.54888 (12)0.0447 (8)
C40.8626 (3)0.3300 (4)0.66929 (12)0.0368 (7)
C200.4324 (3)0.0105 (5)0.74858 (13)0.0502 (9)
H20A0.4070.10750.75780.06*
H20B0.44380.08340.78110.06*
H20C0.37280.06410.72210.06*
C160.6967 (3)0.0869 (5)0.90518 (13)0.0542 (10)
H160.65640.14280.93110.040 (9)*
C190.8167 (3)0.0757 (5)0.82813 (13)0.0472 (9)
H230.85790.13080.80240.070 (12)*
C150.6509 (3)0.0950 (4)0.85003 (12)0.0453 (9)
H150.57990.15540.83920.053 (10)*
C170.8009 (3)0.0025 (5)0.92185 (14)0.0547 (9)
H170.83040.00910.9590.049 (9)*
C90.8402 (4)0.1253 (5)0.52642 (14)0.0733 (13)
H9A0.88150.13060.49480.088*
H9B0.87670.20650.5540.088*
H9C0.75850.15870.51610.088*
C60.7027 (3)0.3966 (4)0.59270 (13)0.0447 (8)
C70.6170 (3)0.3197 (5)0.54709 (13)0.0583 (10)
H7A0.54770.39490.54090.07*
H7B0.65410.31380.51420.07*
H7C0.59410.20120.5570.07*
C210.4265 (4)0.1398 (6)0.60220 (17)0.0945 (16)
H21A0.38770.20150.62920.113*
H21B0.36920.11110.5710.113*
H21C0.48720.21550.59070.113*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.0401 (13)0.0350 (13)0.0488 (13)0.0052 (10)0.0126 (11)0.0110 (10)
O10.0418 (12)0.0347 (12)0.0426 (12)0.0015 (11)0.0005 (10)0.0014 (10)
O50.0428 (12)0.0443 (14)0.0508 (13)0.0014 (12)0.0025 (11)0.0037 (11)
N20.0344 (14)0.0359 (15)0.0321 (13)0.0014 (12)0.0074 (11)0.0018 (11)
N10.0425 (15)0.0312 (15)0.0321 (13)0.0018 (12)0.0112 (11)0.0047 (11)
O20.085 (2)0.0352 (15)0.097 (2)0.0149 (14)0.0102 (16)0.0020 (14)
O30.090 (2)0.0705 (18)0.0466 (14)0.0058 (16)0.0300 (14)0.0199 (13)
N30.0374 (14)0.0392 (15)0.0323 (14)0.0012 (13)0.0065 (12)0.0003 (12)
C120.0347 (16)0.0288 (17)0.0449 (18)0.0007 (15)0.0107 (14)0.0002 (14)
C30.0343 (17)0.0297 (16)0.0366 (16)0.0005 (14)0.0061 (14)0.0047 (14)
C100.0433 (19)0.051 (2)0.057 (2)0.0004 (18)0.0139 (17)0.0061 (18)
C140.0413 (17)0.0307 (17)0.0382 (16)0.0014 (16)0.0125 (14)0.0039 (14)
C130.0428 (17)0.0262 (16)0.0371 (16)0.0019 (15)0.0129 (14)0.0003 (14)
C180.058 (2)0.045 (2)0.054 (2)0.008 (2)0.0054 (19)0.0035 (18)
C110.0350 (17)0.0273 (16)0.0433 (17)0.0030 (15)0.0033 (14)0.0008 (14)
C10.0400 (18)0.0269 (17)0.0406 (17)0.0013 (15)0.0087 (14)0.0038 (14)
C50.050 (2)0.0374 (19)0.061 (2)0.0007 (18)0.0033 (17)0.0117 (17)
C20.0358 (17)0.0303 (16)0.0343 (16)0.0004 (15)0.0073 (13)0.0028 (13)
C80.0437 (19)0.056 (2)0.0349 (17)0.0011 (17)0.0067 (15)0.0033 (16)
C40.0388 (18)0.0306 (17)0.0424 (18)0.0011 (16)0.0104 (15)0.0051 (15)
C200.0445 (19)0.048 (2)0.061 (2)0.0019 (18)0.0172 (17)0.0056 (18)
C160.065 (3)0.059 (2)0.042 (2)0.009 (2)0.0195 (19)0.0078 (18)
C190.051 (2)0.047 (2)0.0448 (19)0.0063 (18)0.0087 (17)0.0004 (17)
C150.053 (2)0.043 (2)0.0428 (19)0.0061 (18)0.0163 (17)0.0009 (16)
C170.072 (3)0.052 (2)0.038 (2)0.009 (2)0.0002 (19)0.0022 (18)
C90.104 (3)0.069 (3)0.052 (2)0.009 (3)0.031 (2)0.023 (2)
C60.047 (2)0.036 (2)0.051 (2)0.0022 (17)0.0069 (16)0.0056 (16)
C70.058 (2)0.056 (2)0.057 (2)0.006 (2)0.0073 (18)0.0136 (19)
C210.109 (4)0.076 (3)0.085 (3)0.025 (3)0.040 (3)0.004 (3)
Geometric parameters (Å, º) top
O4—C11.376 (3)C18—C191.382 (4)
O4—H40.82C18—H180.93
O1—C41.345 (3)C1—C21.599 (4)
O1—C11.469 (3)C5—C41.483 (4)
O5—C111.349 (3)C5—H5A0.96
O5—C211.415 (4)C5—H5B0.96
N2—C111.349 (4)C5—H5C0.96
N2—N31.355 (3)C2—C81.540 (4)
N2—N11.400 (3)C8—C91.500 (5)
N1—C21.484 (4)C20—H20A0.96
N1—H10.9786C20—H20B0.96
O2—C61.226 (4)C20—H20C0.96
O3—C81.201 (4)C16—C171.370 (5)
N3—C131.334 (3)C16—C151.386 (4)
C12—C111.373 (4)C16—H160.93
C12—C131.415 (4)C19—H230.93
C12—C201.499 (4)C15—H150.93
C3—C41.357 (4)C17—H170.93
C3—C61.450 (4)C9—H9A0.96
C3—C21.508 (4)C9—H9B0.96
C10—C11.503 (4)C9—H9C0.96
C10—H10C0.96C6—C71.496 (4)
C10—H10A0.96C7—H7A0.96
C10—H10B0.96C7—H7B0.96
C14—C191.388 (4)C7—H7C0.96
C14—C151.388 (4)C21—H21A0.96
C14—C131.478 (4)C21—H21B0.96
C18—C171.380 (5)C21—H21C0.96
C1—O4—H4109.5N1—C2—C1115.1 (2)
C4—O1—C1108.9 (2)C3—C2—C1101.5 (2)
C11—O5—C21115.2 (3)C8—C2—C1108.8 (2)
C11—N2—N3111.8 (2)O3—C8—C9120.9 (3)
C11—N2—N1125.7 (2)O3—C8—C2120.7 (3)
N3—N2—N1122.2 (2)C9—C8—C2118.4 (3)
N2—N1—C2116.0 (2)O1—C4—C3115.0 (3)
N2—N1—H1107.7O1—C4—C5113.7 (3)
C2—N1—H1114C3—C4—C5131.2 (3)
C13—N3—N2104.8 (2)C12—C20—H20A109.5
C11—C12—C13103.9 (2)C12—C20—H20B109.5
C11—C12—C20126.3 (3)H20A—C20—H20B109.5
C13—C12—C20129.8 (3)C12—C20—H20C109.5
C4—C3—C6124.3 (3)H20A—C20—H20C109.5
C4—C3—C2108.1 (3)H20B—C20—H20C109.5
C6—C3—C2127.6 (3)C17—C16—C15120.6 (3)
C1—C10—H10C109.5C17—C16—H16119.7
C1—C10—H10A109.5C15—C16—H16119.7
H10C—C10—H10A109.5C18—C19—C14120.7 (3)
C1—C10—H10B109.5C18—C19—H23119.7
H10C—C10—H10B109.5C14—C19—H23119.7
H10A—C10—H10B109.5C16—C15—C14120.2 (3)
C19—C14—C15118.7 (3)C16—C15—H15119.9
C19—C14—C13119.3 (3)C14—C15—H15119.9
C15—C14—C13122.0 (3)C16—C17—C18119.7 (3)
N3—C13—C12111.7 (2)C16—C17—H17120.2
N3—C13—C14118.4 (3)C18—C17—H17120.2
C12—C13—C14129.9 (3)C8—C9—H9A109.5
C17—C18—C19120.1 (3)C8—C9—H9B109.5
C17—C18—H18119.9H9A—C9—H9B109.5
C19—C18—H18119.9C8—C9—H9C109.5
O5—C11—N2121.5 (3)H9A—C9—H9C109.5
O5—C11—C12130.5 (3)H9B—C9—H9C109.5
N2—C11—C12107.9 (3)O2—C6—C3121.9 (3)
O4—C1—O1108.7 (2)O2—C6—C7118.5 (3)
O4—C1—C10108.6 (3)C3—C6—C7119.6 (3)
O1—C1—C10106.6 (2)C6—C7—H7A109.5
O4—C1—C2113.9 (2)C6—C7—H7B109.5
O1—C1—C2103.4 (2)H7A—C7—H7B109.5
C10—C1—C2115.2 (2)C6—C7—H7C109.5
C4—C5—H5A109.5H7A—C7—H7C109.5
C4—C5—H5B109.5H7B—C7—H7C109.5
H5A—C5—H5B109.5O5—C21—H21A109.5
C4—C5—H5C109.5O5—C21—H21B109.5
H5A—C5—H5C109.5H21A—C21—H21B109.5
H5B—C5—H5C109.5O5—C21—H21C109.5
N1—C2—C3112.1 (2)H21A—C21—H21C109.5
N1—C2—C8104.9 (2)H21B—C21—H21C109.5
C3—C2—C8114.7 (2)
C11—N2—N1—C2127.9 (3)C6—C3—C2—C1167.7 (3)
N3—N2—N1—C258.5 (3)O4—C1—C2—N113.4 (3)
C11—N2—N3—C131.5 (3)O1—C1—C2—N1104.3 (3)
N1—N2—N3—C13175.9 (2)C10—C1—C2—N1139.9 (3)
N2—N3—C13—C121.9 (3)O4—C1—C2—C3134.7 (2)
N2—N3—C13—C14174.9 (2)O1—C1—C2—C317.0 (3)
C11—C12—C13—N31.6 (3)C10—C1—C2—C398.8 (3)
C20—C12—C13—N3178.6 (3)O4—C1—C2—C8103.9 (3)
C11—C12—C13—C14174.7 (3)O1—C1—C2—C8138.3 (2)
C20—C12—C13—C145.1 (5)C10—C1—C2—C822.5 (3)
C19—C14—C13—N335.7 (4)N1—C2—C8—O3144.1 (3)
C15—C14—C13—N3143.9 (3)C3—C2—C8—O320.7 (4)
C19—C14—C13—C12140.5 (3)C1—C2—C8—O392.2 (4)
C15—C14—C13—C1240.0 (5)N1—C2—C8—C938.0 (4)
C21—O5—C11—N292.7 (4)C3—C2—C8—C9161.5 (3)
C21—O5—C11—C1291.4 (4)C1—C2—C8—C985.6 (4)
N3—N2—C11—O5177.3 (2)C1—O1—C4—C37.7 (3)
N1—N2—C11—O58.5 (4)C1—O1—C4—C5173.9 (2)
N3—N2—C11—C120.5 (3)C6—C3—C4—O1176.5 (3)
N1—N2—C11—C12174.7 (3)C2—C3—C4—O14.6 (3)
C13—C12—C11—O5175.7 (3)C6—C3—C4—C55.4 (5)
C20—C12—C11—O54.1 (5)C2—C3—C4—C5173.5 (3)
C13—C12—C11—N20.6 (3)C17—C18—C19—C140.5 (5)
C20—C12—C11—N2179.5 (3)C15—C14—C19—C180.2 (5)
C4—O1—C1—O4136.8 (2)C13—C14—C19—C18179.8 (3)
C4—O1—C1—C10106.3 (3)C17—C16—C15—C140.4 (5)
C4—O1—C1—C215.5 (3)C19—C14—C15—C160.3 (5)
N2—N1—C2—C345.8 (3)C13—C14—C15—C16179.8 (3)
N2—N1—C2—C8171.0 (2)C15—C16—C17—C181.1 (5)
N2—N1—C2—C169.5 (3)C19—C18—C17—C161.2 (5)
C4—C3—C2—N1110.0 (3)C4—C3—C6—O212.2 (5)
C6—C3—C2—N168.9 (4)C2—C3—C6—O2169.1 (3)
C4—C3—C2—C8130.5 (3)C4—C3—C6—C7169.8 (3)
C6—C3—C2—C850.6 (4)C2—C3—C6—C78.9 (5)
C4—C3—C2—C113.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.982.173.056 (3)150
O4—H4···N20.822.613.149 (3)125
O4—H4···N30.821.972.720 (3)152
C5—H5A···O20.962.382.948 (4)117
C5—H5C···O4ii0.962.523.293 (4)138
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z.
 

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