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In the title mol­ecule, the five- and six-membered rings are oriented at a dihedral angle of 75.88 (8)°. In the crystal, N—H⋯N hydrogen bonds form chains of mol­ecules extending along the c-axis direction that are connected by inversion-related pairs of O—H⋯N into ribbons. The ribbons are linked by C—H⋯π(ring) inter­actions, forming layers parallel to the ab plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989024000744/ny2002sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989024000744/ny2002Isup2.hkl
Contains datablock I

cdx

Chemdraw file https://doi.org/10.1107/S2056989024000744/ny2002Isup3.cdx
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989024000744/ny2002Isup4.cml
Supplementary material

CCDC reference: 2327436

Computing details top

Ethyl 2-cyano-3-(3-hydroxy-5-methyl-1H-pyrazol-4-yl)-3-phenylpropanoate top
Crystal data top
C16H17N3O3Z = 2
Mr = 299.32F(000) = 316
Triclinic, P1Dx = 1.300 Mg m3
a = 9.1397 (2) ÅCu Kα radiation, λ = 1.54178 Å
b = 9.4879 (2) ÅCell parameters from 8141 reflections
c = 10.0063 (2) Åθ = 4.7–72.2°
α = 79.554 (1)°µ = 0.75 mm1
β = 63.787 (1)°T = 150 K
γ = 83.054 (1)°Prism, clear colourless
V = 764.75 (3) Å30.16 × 0.09 × 0.03 mm
Data collection top
Bruker D8 VENTURE PHOTON 3 CPAD
diffractometer
2998 independent reflections
Radiation source: INCOATEC IµS micro–focus source2207 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.112
Detector resolution: 7.3910 pixels mm-1θmax = 72.4°, θmin = 4.7°
φ and ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
k = 1111
Tmin = 0.88, Tmax = 0.98l = 1212
36885 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: mixed
wR(F2) = 0.127H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0565P)2 + 0.3004P]
where P = (Fo2 + 2Fc2)/3
2998 reflections(Δ/σ)max < 0.001
207 parametersΔρmax = 0.19 e Å3
2 restraintsΔρmin = 0.23 e Å3
Special details top

Experimental. The diffraction data were obtained from sets of frames, each of width 0.5° in ω or φ, collected with scan parameters determined by the "strategy" routine in APEX4. The scan time was sec/frame.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 1.00 Å) and were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. Those attached to nitrogen and to oxygen were placed in locations derived from a difference map and refined with DFIX 0.91 0.01 and DFIX 0.85 0.01 instructions, respectively.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.31072 (17)0.88849 (16)0.53196 (17)0.0374 (4)
O20.34195 (18)0.66225 (16)0.47923 (18)0.0396 (4)
O30.5608 (2)0.97967 (16)0.16765 (17)0.0380 (4)
H30.510 (3)1.038 (2)0.124 (3)0.057*
N10.6348 (2)0.70329 (19)0.03454 (19)0.0340 (4)
H10.641 (3)0.670 (3)0.1172 (19)0.051*
N20.5886 (2)0.84391 (19)0.01623 (19)0.0327 (4)
N30.6355 (2)0.7145 (2)0.6688 (2)0.0441 (5)
C10.0507 (3)0.8091 (3)0.7386 (3)0.0574 (7)
H1A0.0678050.8246700.7746570.086*
H1B0.0853420.8447190.8056610.086*
H1C0.0797720.7062920.7376770.086*
C20.1346 (3)0.8881 (3)0.5822 (3)0.0453 (6)
H2A0.1122750.8423760.5120740.054*
H2B0.0894100.9882760.5797370.054*
C30.3974 (2)0.7698 (2)0.4823 (2)0.0306 (4)
C40.5793 (2)0.7876 (2)0.4307 (2)0.0278 (4)
H40.6042610.8904740.3890340.033*
C50.6124 (2)0.7486 (2)0.5641 (2)0.0333 (5)
C60.5994 (2)0.8562 (2)0.1099 (2)0.0301 (4)
C70.6532 (2)0.7267 (2)0.1720 (2)0.0278 (4)
C80.6750 (2)0.6317 (2)0.0746 (2)0.0316 (4)
C90.7316 (3)0.4776 (2)0.0780 (3)0.0443 (6)
H9A0.6808210.4283990.0322570.066*
H9B0.7005040.4329220.1825800.066*
H9C0.8505730.4701040.0215220.066*
C100.6881 (2)0.6924 (2)0.3084 (2)0.0277 (4)
H100.6609230.5903880.3524630.033*
C110.8671 (2)0.7065 (2)0.2704 (2)0.0276 (4)
C120.9482 (2)0.5996 (2)0.3305 (2)0.0335 (5)
H120.8929430.5162950.3914470.040*
C131.1095 (3)0.6133 (3)0.3023 (2)0.0391 (5)
H131.1637650.5394420.3439210.047*
C141.1906 (3)0.7340 (3)0.2139 (3)0.0410 (5)
H141.3002350.7441390.1957750.049*
C151.1118 (3)0.8403 (3)0.1519 (3)0.0399 (5)
H151.1680560.9228940.0900370.048*
C160.9514 (3)0.8269 (2)0.1793 (2)0.0356 (5)
H160.8984460.9001960.1357820.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0302 (8)0.0378 (8)0.0425 (9)0.0015 (6)0.0144 (6)0.0070 (7)
O20.0342 (8)0.0396 (9)0.0476 (9)0.0058 (6)0.0179 (7)0.0090 (7)
O30.0555 (10)0.0341 (8)0.0356 (8)0.0037 (7)0.0318 (7)0.0034 (6)
N10.0400 (10)0.0407 (10)0.0253 (8)0.0016 (7)0.0176 (7)0.0055 (7)
N20.0360 (9)0.0390 (10)0.0265 (8)0.0032 (7)0.0173 (7)0.0013 (7)
N30.0489 (12)0.0569 (13)0.0323 (10)0.0084 (9)0.0241 (9)0.0097 (9)
C10.0411 (14)0.0526 (16)0.0616 (17)0.0039 (11)0.0058 (12)0.0099 (13)
C20.0330 (12)0.0523 (14)0.0522 (14)0.0081 (10)0.0198 (10)0.0138 (11)
C30.0314 (10)0.0362 (11)0.0256 (10)0.0001 (8)0.0145 (8)0.0027 (8)
C40.0304 (10)0.0312 (10)0.0241 (9)0.0026 (8)0.0148 (8)0.0003 (8)
C50.0320 (11)0.0404 (12)0.0294 (10)0.0002 (8)0.0150 (9)0.0061 (9)
C60.0312 (10)0.0385 (11)0.0245 (9)0.0039 (8)0.0154 (8)0.0035 (8)
C70.0264 (9)0.0358 (11)0.0218 (9)0.0037 (7)0.0117 (7)0.0004 (8)
C80.0333 (10)0.0367 (11)0.0257 (9)0.0043 (8)0.0143 (8)0.0011 (8)
C90.0606 (15)0.0409 (13)0.0370 (12)0.0051 (11)0.0265 (11)0.0095 (10)
C100.0319 (10)0.0275 (10)0.0264 (9)0.0037 (7)0.0161 (8)0.0004 (8)
C110.0291 (10)0.0324 (10)0.0232 (9)0.0018 (8)0.0127 (8)0.0041 (8)
C120.0349 (11)0.0376 (12)0.0291 (10)0.0014 (9)0.0160 (9)0.0017 (9)
C130.0340 (11)0.0511 (14)0.0359 (11)0.0050 (9)0.0204 (9)0.0054 (10)
C140.0293 (11)0.0595 (15)0.0378 (12)0.0053 (10)0.0152 (9)0.0119 (10)
C150.0380 (12)0.0437 (13)0.0374 (12)0.0119 (10)0.0146 (9)0.0021 (10)
C160.0359 (11)0.0360 (12)0.0346 (11)0.0048 (9)0.0167 (9)0.0019 (9)
Geometric parameters (Å, º) top
O1—C31.335 (2)C6—C71.409 (3)
O1—C21.460 (3)C7—C81.380 (3)
O2—C31.204 (2)C7—C101.506 (3)
O3—C61.340 (2)C8—C91.490 (3)
O3—H30.857 (10)C9—H9A0.9800
N1—C81.348 (3)C9—H9B0.9800
N1—N21.370 (2)C9—H9C0.9800
N1—H10.914 (10)C10—C111.524 (3)
N2—C61.335 (2)C10—H101.0000
N3—C51.141 (3)C11—C121.389 (3)
C1—C21.501 (4)C11—C161.394 (3)
C1—H1A0.9800C12—C131.391 (3)
C1—H1B0.9800C12—H120.9500
C1—H1C0.9800C13—C141.379 (3)
C2—H2A0.9900C13—H130.9500
C2—H2B0.9900C14—C151.383 (3)
C3—C41.529 (3)C14—H140.9500
C4—C51.470 (3)C15—C161.385 (3)
C4—C101.552 (3)C15—H150.9500
C4—H41.0000C16—H160.9500
C3—O1—C2116.68 (17)N1—C8—C7107.38 (18)
C6—O3—H3109.6 (19)N1—C8—C9122.35 (18)
C8—N1—N2112.28 (16)C7—C8—C9130.27 (18)
C8—N1—H1127.6 (17)C8—C9—H9A109.5
N2—N1—H1120.0 (17)C8—C9—H9B109.5
C6—N2—N1103.85 (16)H9A—C9—H9B109.5
C2—C1—H1A109.5C8—C9—H9C109.5
C2—C1—H1B109.5H9A—C9—H9C109.5
H1A—C1—H1B109.5H9B—C9—H9C109.5
C2—C1—H1C109.5C7—C10—C11112.75 (16)
H1A—C1—H1C109.5C7—C10—C4111.51 (16)
H1B—C1—H1C109.5C11—C10—C4109.52 (15)
O1—C2—C1111.9 (2)C7—C10—H10107.6
O1—C2—H2A109.2C11—C10—H10107.6
C1—C2—H2A109.2C4—C10—H10107.6
O1—C2—H2B109.2C12—C11—C16118.64 (18)
C1—C2—H2B109.2C12—C11—C10119.87 (17)
H2A—C2—H2B107.9C16—C11—C10121.46 (18)
O2—C3—O1125.49 (19)C11—C12—C13120.77 (19)
O2—C3—C4123.93 (19)C11—C12—H12119.6
O1—C3—C4110.57 (17)C13—C12—H12119.6
C5—C4—C3107.30 (16)C14—C13—C12120.0 (2)
C5—C4—C10110.20 (16)C14—C13—H13120.0
C3—C4—C10112.11 (15)C12—C13—H13120.0
C5—C4—H4109.1C13—C14—C15119.8 (2)
C3—C4—H4109.1C13—C14—H14120.1
C10—C4—H4109.1C15—C14—H14120.1
N3—C5—C4177.9 (2)C14—C15—C16120.4 (2)
N2—C6—O3122.06 (18)C14—C15—H15119.8
N2—C6—C7112.33 (18)C16—C15—H15119.8
O3—C6—C7125.61 (17)C15—C16—C11120.4 (2)
C8—C7—C6104.16 (17)C15—C16—H16119.8
C8—C7—C10125.22 (18)C11—C16—H16119.8
C6—C7—C10130.58 (18)
C8—N1—N2—C60.9 (2)C8—C7—C10—C1183.8 (2)
C3—O1—C2—C179.9 (2)C6—C7—C10—C1193.6 (2)
C2—O1—C3—O21.9 (3)C8—C7—C10—C4152.51 (19)
C2—O1—C3—C4178.73 (17)C6—C7—C10—C430.1 (3)
O2—C3—C4—C593.5 (2)C5—C4—C10—C7178.19 (16)
O1—C3—C4—C585.9 (2)C3—C4—C10—C758.8 (2)
O2—C3—C4—C1027.6 (3)C5—C4—C10—C1156.3 (2)
O1—C3—C4—C10152.99 (16)C3—C4—C10—C11175.76 (15)
N1—N2—C6—O3178.86 (18)C7—C10—C11—C12133.87 (19)
N1—N2—C6—C70.7 (2)C4—C10—C11—C12101.4 (2)
N2—C6—C7—C80.2 (2)C7—C10—C11—C1647.9 (3)
O3—C6—C7—C8179.32 (19)C4—C10—C11—C1676.9 (2)
N2—C6—C7—C10177.66 (19)C16—C11—C12—C131.0 (3)
O3—C6—C7—C102.8 (3)C10—C11—C12—C13177.28 (18)
N2—N1—C8—C70.9 (2)C11—C12—C13—C140.0 (3)
N2—N1—C8—C9179.08 (19)C12—C13—C14—C150.9 (3)
C6—C7—C8—N10.4 (2)C13—C14—C15—C160.7 (3)
C10—C7—C8—N1178.39 (17)C14—C15—C16—C110.3 (3)
C6—C7—C8—C9179.5 (2)C12—C11—C16—C151.2 (3)
C10—C7—C8—C91.5 (3)C10—C11—C16—C15177.08 (19)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the five-membered ring.
D—H···AD—HH···AD···AD—H···A
O3—H3···N2i0.86 (1)1.85 (1)2.706 (2)175 (3)
N1—H1···N3ii0.91 (1)2.13 (2)2.948 (2)149 (2)
C14—H14···Cg1iii0.952.713.627 (3)162
Symmetry codes: (i) x+1, y+2, z; (ii) x, y, z1; (iii) x+1, y, z.
Comparison of selected X-ray and DFT geometric data (Å, °) top
Bonds/anglesX-rayB3LYP/6-311G(d,p)
O1—C31.335 (2)1.345
O1—C21.460 (3)1.521
O2—C31.204 (2)1.235
O3—C61.340 (2)1.337
N1—C81.348 (3)1.331
N1—N21.368 (2)1.377
N1—H10.914 (10)0.87
N2—C61.335 (2)1.322
N3—C51.141 (3)1.128
C3—O1—C2116.67 (17)115.6
C8—N1—N2112.35 (16)113.1
C6—N2—N1103.86 (16)104.6
O2—C3—O1125.51 (19)124.5
N2—C6—O3122.03 (18)123.1
Calculated energies top
Molecular energy (a.u.) (eV)Compound (I)
ELUMO (eV)-0.82
EHOMO (eV)-6.59
Gap ΔE (eV)5.77
Ionization potential I6.59
Electron affinity A0.82
Chemical hardness η2.88
Chemical softness σ0.17
Electronegativity χ3.70
Chemical potential µ-3.71
Electrophilicity index ω2.38
Total energy TE (eV)-27476.33
 

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