1-[(2RS,3RS)-4-Acetyl-2-hydroxy-3-(5-methoxy-4-methyl-3-phenyl­pyrazol-1-yl­amino)-2,5-di­methyl-2,3-di­hydrofuran-3-yl]­ethano­ne

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.

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

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Computing details

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

Crystal data

C21H25N3O5	F(000) = 848
Mr = 399.44	Dx = 1.292 Mg m^−3
Monoclinic, P21/c	Melting point: 387 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.339 (3) Å	Cell parameters from 35 reflections
b = 7.444 (2) Å	θ = 4–38°
c = 24.546 (4) Å	µ = 0.09 mm^−1
β = 97.61 (1)°	T = 293 K
V = 2053.6 (8) Å^3	Needle, colourless
Z = 4	0.4 × 0.2 × 0.2 mm

Data collection

Siemens P4 diffractometer	Rint = 0.031
Radiation source: sealed tube	θmax = 25°, θmin = 1.8°
Graphite monochromator	h = −1→13
ω scans	k = −1→8
4895 measured reflections	l = −29→29
3612 independent reflections	3 standard reflections every 97 reflections
1988 reflections with I > 2σ(I)	intensity decay: <1%

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.056	w = 1/[σ^2(Fo^2) + (0.059P)^2 + 0.0883P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.139	(Δ/σ)max = 0.011
S = 1.01	Δρmax = 0.17 e Å^−3
3612 reflections	Δρmin = −0.26 e Å^−3
276 parameters

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O4	0.95159 (19)	0.0998 (3)	0.67593 (9)	0.0407 (6)
H4	0.8988	0.1048	0.6957	0.072 (14)*
O1	0.94465 (17)	−0.2075 (3)	0.68887 (7)	0.0401 (5)
O5	0.47868 (18)	−0.0204 (3)	0.62516 (8)	0.0468 (6)
N2	0.6771 (2)	0.0180 (3)	0.66575 (9)	0.0339 (6)
N1	0.7265 (2)	0.0365 (3)	0.61673 (9)	0.0347 (6)
H1	0.7483	0.1629	0.6132	0.040 (8)*
O2	0.6968 (2)	−0.5574 (3)	0.60277 (11)	0.0742 (8)
O3	0.8716 (2)	−0.1866 (4)	0.52146 (9)	0.0673 (8)
N3	0.7434 (2)	0.0313 (3)	0.71573 (9)	0.0361 (6)
C12	0.5472 (3)	0.0030 (4)	0.72479 (12)	0.0356 (7)
C3	0.7924 (3)	−0.2816 (4)	0.62245 (11)	0.0334 (7)
C10	1.0562 (3)	−0.0852 (5)	0.62198 (13)	0.0497 (9)
H10C	1.0634	0.0129	0.5973	0.06*
H10A	1.0519	−0.1962	0.6019	0.06*
H10B	1.1241	−0.0871	0.6498	0.06*
C14	0.7106 (3)	0.0130 (4)	0.81087 (12)	0.0361 (7)
C13	0.6651 (3)	0.0187 (4)	0.75161 (11)	0.0347 (7)
C18	0.8617 (3)	−0.0828 (5)	0.88322 (14)	0.0532 (9)
H18	0.9332	−0.1418	0.8943	0.056 (10)*
C11	0.5601 (3)	0.0020 (4)	0.66994 (12)	0.0354 (7)
C1	0.9451 (3)	−0.0619 (4)	0.64851 (11)	0.0355 (7)
C5	0.8627 (3)	−0.4933 (4)	0.70387 (13)	0.0499 (9)
H5A	0.7876	−0.5536	0.6959	0.06*
H5B	0.8754	−0.4598	0.742	0.06*
H5C	0.9253	−0.5723	0.6961	0.06*
C2	0.8231 (3)	−0.0914 (4)	0.60870 (11)	0.0332 (7)
C8	0.8461 (3)	−0.0624 (5)	0.54888 (12)	0.0447 (8)
C4	0.8626 (3)	−0.3300 (4)	0.66929 (12)	0.0368 (7)
C20	0.4324 (3)	−0.0105 (5)	0.74858 (13)	0.0502 (9)
H20A	0.407	0.1075	0.7578	0.06*
H20B	0.4438	−0.0834	0.7811	0.06*
H20C	0.3728	−0.0641	0.7221	0.06*
C16	0.6967 (3)	0.0869 (5)	0.90518 (13)	0.0542 (10)
H16	0.6564	0.1428	0.9311	0.040 (9)*
C19	0.8167 (3)	−0.0757 (5)	0.82813 (13)	0.0472 (9)
H23	0.8579	−0.1308	0.8024	0.070 (12)*
C15	0.6509 (3)	0.0950 (4)	0.85003 (12)	0.0453 (9)
H15	0.5799	0.1554	0.8392	0.053 (10)*
C17	0.8009 (3)	−0.0025 (5)	0.92185 (14)	0.0547 (9)
H17	0.8304	−0.0091	0.959	0.049 (9)*
C9	0.8402 (4)	0.1253 (5)	0.52642 (14)	0.0733 (13)
H9A	0.8815	0.1306	0.4948	0.088*
H9B	0.8767	0.2065	0.554	0.088*
H9C	0.7585	0.1587	0.5161	0.088*
C6	0.7027 (3)	−0.3966 (4)	0.59270 (13)	0.0447 (8)
C7	0.6170 (3)	−0.3197 (5)	0.54709 (13)	0.0583 (10)
H7A	0.5477	−0.3949	0.5409	0.07*
H7B	0.6541	−0.3138	0.5142	0.07*
H7C	0.5941	−0.2012	0.557	0.07*
C21	0.4265 (4)	0.1398 (6)	0.60220 (17)	0.0945 (16)
H21A	0.3877	0.2015	0.6292	0.113*
H21B	0.3692	0.1111	0.571	0.113*
H21C	0.4872	0.2155	0.5907	0.113*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O4	0.0401 (13)	0.0350 (13)	0.0488 (13)	−0.0052 (10)	0.0126 (11)	−0.0110 (10)
O1	0.0418 (12)	0.0347 (12)	0.0426 (12)	−0.0015 (11)	0.0005 (10)	0.0014 (10)
O5	0.0428 (12)	0.0443 (14)	0.0508 (13)	0.0014 (12)	−0.0025 (11)	−0.0037 (11)
N2	0.0344 (14)	0.0359 (15)	0.0321 (13)	0.0014 (12)	0.0074 (11)	0.0018 (11)
N1	0.0425 (15)	0.0312 (15)	0.0321 (13)	0.0018 (12)	0.0112 (11)	0.0047 (11)
O2	0.085 (2)	0.0352 (15)	0.097 (2)	−0.0149 (14)	−0.0102 (16)	−0.0020 (14)
O3	0.090 (2)	0.0705 (18)	0.0466 (14)	−0.0058 (16)	0.0300 (14)	−0.0199 (13)
N3	0.0374 (14)	0.0392 (15)	0.0323 (14)	0.0012 (13)	0.0065 (12)	0.0003 (12)
C12	0.0347 (16)	0.0288 (17)	0.0449 (18)	−0.0007 (15)	0.0107 (14)	0.0002 (14)
C3	0.0343 (17)	0.0297 (16)	0.0366 (16)	−0.0005 (14)	0.0061 (14)	−0.0047 (14)
C10	0.0433 (19)	0.051 (2)	0.057 (2)	−0.0004 (18)	0.0139 (17)	−0.0061 (18)
C14	0.0413 (17)	0.0307 (17)	0.0382 (16)	0.0014 (16)	0.0125 (14)	0.0039 (14)
C13	0.0428 (17)	0.0262 (16)	0.0371 (16)	0.0019 (15)	0.0129 (14)	−0.0003 (14)
C18	0.058 (2)	0.045 (2)	0.054 (2)	0.008 (2)	−0.0054 (19)	0.0035 (18)
C11	0.0350 (17)	0.0273 (16)	0.0433 (17)	0.0030 (15)	0.0033 (14)	−0.0008 (14)
C1	0.0400 (18)	0.0269 (17)	0.0406 (17)	−0.0013 (15)	0.0087 (14)	−0.0038 (14)
C5	0.050 (2)	0.0374 (19)	0.061 (2)	0.0007 (18)	0.0033 (17)	0.0117 (17)
C2	0.0358 (17)	0.0303 (16)	0.0343 (16)	0.0004 (15)	0.0073 (13)	−0.0028 (13)
C8	0.0437 (19)	0.056 (2)	0.0349 (17)	−0.0011 (17)	0.0067 (15)	−0.0033 (16)
C4	0.0388 (18)	0.0306 (17)	0.0424 (18)	0.0011 (16)	0.0104 (15)	−0.0051 (15)
C20	0.0445 (19)	0.048 (2)	0.061 (2)	−0.0019 (18)	0.0172 (17)	−0.0056 (18)
C16	0.065 (3)	0.059 (2)	0.042 (2)	−0.009 (2)	0.0195 (19)	−0.0078 (18)
C19	0.051 (2)	0.047 (2)	0.0448 (19)	0.0063 (18)	0.0087 (17)	−0.0004 (17)
C15	0.053 (2)	0.043 (2)	0.0428 (19)	0.0061 (18)	0.0163 (17)	0.0009 (16)
C17	0.072 (3)	0.052 (2)	0.038 (2)	−0.009 (2)	0.0002 (19)	0.0022 (18)
C9	0.104 (3)	0.069 (3)	0.052 (2)	0.009 (3)	0.031 (2)	0.023 (2)
C6	0.047 (2)	0.036 (2)	0.051 (2)	−0.0022 (17)	0.0069 (16)	−0.0056 (16)
C7	0.058 (2)	0.056 (2)	0.057 (2)	−0.006 (2)	−0.0073 (18)	−0.0136 (19)
C21	0.109 (4)	0.076 (3)	0.085 (3)	0.025 (3)	−0.040 (3)	0.004 (3)

Geometric parameters (Å, º)

O4—C1	1.376 (3)	C18—C19	1.382 (4)
O4—H4	0.82	C18—H18	0.93
O1—C4	1.345 (3)	C1—C2	1.599 (4)
O1—C1	1.469 (3)	C5—C4	1.483 (4)
O5—C11	1.349 (3)	C5—H5A	0.96
O5—C21	1.415 (4)	C5—H5B	0.96
N2—C11	1.349 (4)	C5—H5C	0.96
N2—N3	1.355 (3)	C2—C8	1.540 (4)
N2—N1	1.400 (3)	C8—C9	1.500 (5)
N1—C2	1.484 (4)	C20—H20A	0.96
N1—H1	0.9786	C20—H20B	0.96
O2—C6	1.226 (4)	C20—H20C	0.96
O3—C8	1.201 (4)	C16—C17	1.370 (5)
N3—C13	1.334 (3)	C16—C15	1.386 (4)
C12—C11	1.373 (4)	C16—H16	0.93
C12—C13	1.415 (4)	C19—H23	0.93
C12—C20	1.499 (4)	C15—H15	0.93
C3—C4	1.357 (4)	C17—H17	0.93
C3—C6	1.450 (4)	C9—H9A	0.96
C3—C2	1.508 (4)	C9—H9B	0.96
C10—C1	1.503 (4)	C9—H9C	0.96
C10—H10C	0.96	C6—C7	1.496 (4)
C10—H10A	0.96	C7—H7A	0.96
C10—H10B	0.96	C7—H7B	0.96
C14—C19	1.388 (4)	C7—H7C	0.96
C14—C15	1.388 (4)	C21—H21A	0.96
C14—C13	1.478 (4)	C21—H21B	0.96
C18—C17	1.380 (5)	C21—H21C	0.96
C1—O4—H4	109.5	N1—C2—C1	115.1 (2)
C4—O1—C1	108.9 (2)	C3—C2—C1	101.5 (2)
C11—O5—C21	115.2 (3)	C8—C2—C1	108.8 (2)
C11—N2—N3	111.8 (2)	O3—C8—C9	120.9 (3)
C11—N2—N1	125.7 (2)	O3—C8—C2	120.7 (3)
N3—N2—N1	122.2 (2)	C9—C8—C2	118.4 (3)
N2—N1—C2	116.0 (2)	O1—C4—C3	115.0 (3)
N2—N1—H1	107.7	O1—C4—C5	113.7 (3)
C2—N1—H1	114	C3—C4—C5	131.2 (3)
C13—N3—N2	104.8 (2)	C12—C20—H20A	109.5
C11—C12—C13	103.9 (2)	C12—C20—H20B	109.5
C11—C12—C20	126.3 (3)	H20A—C20—H20B	109.5
C13—C12—C20	129.8 (3)	C12—C20—H20C	109.5
C4—C3—C6	124.3 (3)	H20A—C20—H20C	109.5
C4—C3—C2	108.1 (3)	H20B—C20—H20C	109.5
C6—C3—C2	127.6 (3)	C17—C16—C15	120.6 (3)
C1—C10—H10C	109.5	C17—C16—H16	119.7
C1—C10—H10A	109.5	C15—C16—H16	119.7
H10C—C10—H10A	109.5	C18—C19—C14	120.7 (3)
C1—C10—H10B	109.5	C18—C19—H23	119.7
H10C—C10—H10B	109.5	C14—C19—H23	119.7
H10A—C10—H10B	109.5	C16—C15—C14	120.2 (3)
C19—C14—C15	118.7 (3)	C16—C15—H15	119.9
C19—C14—C13	119.3 (3)	C14—C15—H15	119.9
C15—C14—C13	122.0 (3)	C16—C17—C18	119.7 (3)
N3—C13—C12	111.7 (2)	C16—C17—H17	120.2
N3—C13—C14	118.4 (3)	C18—C17—H17	120.2
C12—C13—C14	129.9 (3)	C8—C9—H9A	109.5
C17—C18—C19	120.1 (3)	C8—C9—H9B	109.5
C17—C18—H18	119.9	H9A—C9—H9B	109.5
C19—C18—H18	119.9	C8—C9—H9C	109.5
O5—C11—N2	121.5 (3)	H9A—C9—H9C	109.5
O5—C11—C12	130.5 (3)	H9B—C9—H9C	109.5
N2—C11—C12	107.9 (3)	O2—C6—C3	121.9 (3)
O4—C1—O1	108.7 (2)	O2—C6—C7	118.5 (3)
O4—C1—C10	108.6 (3)	C3—C6—C7	119.6 (3)
O1—C1—C10	106.6 (2)	C6—C7—H7A	109.5
O4—C1—C2	113.9 (2)	C6—C7—H7B	109.5
O1—C1—C2	103.4 (2)	H7A—C7—H7B	109.5
C10—C1—C2	115.2 (2)	C6—C7—H7C	109.5
C4—C5—H5A	109.5	H7A—C7—H7C	109.5
C4—C5—H5B	109.5	H7B—C7—H7C	109.5
H5A—C5—H5B	109.5	O5—C21—H21A	109.5
C4—C5—H5C	109.5	O5—C21—H21B	109.5
H5A—C5—H5C	109.5	H21A—C21—H21B	109.5
H5B—C5—H5C	109.5	O5—C21—H21C	109.5
N1—C2—C3	112.1 (2)	H21A—C21—H21C	109.5
N1—C2—C8	104.9 (2)	H21B—C21—H21C	109.5
C3—C2—C8	114.7 (2)
C11—N2—N1—C2	−127.9 (3)	C6—C3—C2—C1	−167.7 (3)
N3—N2—N1—C2	58.5 (3)	O4—C1—C2—N1	−13.4 (3)
C11—N2—N3—C13	1.5 (3)	O1—C1—C2—N1	104.3 (3)
N1—N2—N3—C13	175.9 (2)	C10—C1—C2—N1	−139.9 (3)
N2—N3—C13—C12	−1.9 (3)	O4—C1—C2—C3	−134.7 (2)
N2—N3—C13—C14	174.9 (2)	O1—C1—C2—C3	−17.0 (3)
C11—C12—C13—N3	1.6 (3)	C10—C1—C2—C3	98.8 (3)
C20—C12—C13—N3	−178.6 (3)	O4—C1—C2—C8	103.9 (3)
C11—C12—C13—C14	−174.7 (3)	O1—C1—C2—C8	−138.3 (2)
C20—C12—C13—C14	5.1 (5)	C10—C1—C2—C8	−22.5 (3)
C19—C14—C13—N3	−35.7 (4)	N1—C2—C8—O3	−144.1 (3)
C15—C14—C13—N3	143.9 (3)	C3—C2—C8—O3	−20.7 (4)
C19—C14—C13—C12	140.5 (3)	C1—C2—C8—O3	92.2 (4)
C15—C14—C13—C12	−40.0 (5)	N1—C2—C8—C9	38.0 (4)
C21—O5—C11—N2	−92.7 (4)	C3—C2—C8—C9	161.5 (3)
C21—O5—C11—C12	91.4 (4)	C1—C2—C8—C9	−85.6 (4)
N3—N2—C11—O5	−177.3 (2)	C1—O1—C4—C3	−7.7 (3)
N1—N2—C11—O5	8.5 (4)	C1—O1—C4—C5	173.9 (2)
N3—N2—C11—C12	−0.5 (3)	C6—C3—C4—O1	176.5 (3)
N1—N2—C11—C12	−174.7 (3)	C2—C3—C4—O1	−4.6 (3)
C13—C12—C11—O5	175.7 (3)	C6—C3—C4—C5	−5.4 (5)
C20—C12—C11—O5	−4.1 (5)	C2—C3—C4—C5	173.5 (3)
C13—C12—C11—N2	−0.6 (3)	C17—C18—C19—C14	0.5 (5)
C20—C12—C11—N2	179.5 (3)	C15—C14—C19—C18	0.2 (5)
C4—O1—C1—O4	136.8 (2)	C13—C14—C19—C18	179.8 (3)
C4—O1—C1—C10	−106.3 (3)	C17—C16—C15—C14	−0.4 (5)
C4—O1—C1—C2	15.5 (3)	C19—C14—C15—C16	−0.3 (5)
N2—N1—C2—C3	45.8 (3)	C13—C14—C15—C16	−179.8 (3)
N2—N1—C2—C8	171.0 (2)	C15—C16—C17—C18	1.1 (5)
N2—N1—C2—C1	−69.5 (3)	C19—C18—C17—C16	−1.2 (5)
C4—C3—C2—N1	−110.0 (3)	C4—C3—C6—O2	−12.2 (5)
C6—C3—C2—N1	68.9 (4)	C2—C3—C6—O2	169.1 (3)
C4—C3—C2—C8	130.5 (3)	C4—C3—C6—C7	169.8 (3)
C6—C3—C2—C8	−50.6 (4)	C2—C3—C6—C7	−8.9 (5)
C4—C3—C2—C1	13.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.98	2.17	3.056 (3)	150
O4—H4···N2	0.82	2.61	3.149 (3)	125
O4—H4···N3	0.82	1.97	2.720 (3)	152
C5—H5A···O2	0.96	2.38	2.948 (4)	117
C5—H5C···O4^ii	0.96	2.52	3.293 (4)	138

Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z.