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In the title compound, C20H19N3O3, the pyrazolone moiety and the N atom of the 3-amino­propionic acid group are essentially coplanar. The compound is a ligand in an enamine–keto form and its structure is stabilized by two strong intramolecular N—H...O hydrogen bonds. Glide-related mol­ecules form O—H...N hydrogen-bonded chains along the c axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805002023/ci6517sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805002023/ci6517Isup2.hkl
Contains datablock I

CCDC reference: 264084

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.040
  • wR factor = 0.118
  • Data-to-parameter ratio = 16.5

checkCIF/PLATON results

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Alert level C PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293 PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.846(9) ...... 3.33 su-Rat O2 -H2 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

3-{[(1Z)-(3-Methyl-5-oxo-1-phenyl-1,5-dihydropyrazol-4- ylidene)(phenyl)methyl]amino}propionic acid top
Crystal data top
C20H19N3O3F(000) = 1472
Mr = 349.38Dx = 1.264 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2719 reflections
a = 22.779 (3) Åθ = 2.5–22.0°
b = 11.7073 (12) ŵ = 0.09 mm1
c = 16.8032 (16) ÅT = 293 K
β = 124.978 (6)°Block, yellow
V = 3671.7 (8) Å30.42 × 0.38 × 0.34 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
2599 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
Graphite monochromatorθmax = 27.0°, θmin = 2.1°
φ and ω scansh = 2429
10864 measured reflectionsk = 1413
3998 independent reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.052P)2 + 0.9087P]
where P = (Fo2 + 2Fc2)/3
3998 reflections(Δ/σ)max < 0.001
243 parametersΔρmax = 0.15 e Å3
1 restraintΔρmin = 0.14 e Å3
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
N10.13771 (8)0.69052 (11)0.02599 (10)0.0635 (4)
H10.1571 (10)0.6339 (16)0.0104 (13)0.080 (5)*
N20.13817 (7)0.35698 (10)0.10494 (9)0.0573 (3)
N30.10026 (7)0.37172 (11)0.14674 (9)0.0600 (3)
O10.16758 (7)0.68974 (11)0.12209 (9)0.0829 (4)
O20.07346 (7)0.77143 (11)0.25198 (9)0.0742 (4)
H20.0833 (13)0.7260 (16)0.2819 (16)0.111*
O30.17741 (7)0.47255 (9)0.03084 (9)0.0730 (4)
C10.11936 (9)0.75748 (13)0.15757 (12)0.0568 (4)
C20.10486 (9)0.83455 (13)0.09917 (12)0.0606 (4)
H2A0.05480.82810.12330.073*
H2B0.11370.91300.10800.073*
C30.15074 (9)0.80638 (13)0.00779 (12)0.0608 (4)
H3A0.20090.81430.03250.073*
H3B0.14050.86010.04230.073*
C40.11017 (8)0.65889 (12)0.07331 (11)0.0543 (4)
C50.10924 (8)0.54185 (12)0.09143 (11)0.0550 (4)
C60.14510 (9)0.45894 (12)0.06987 (11)0.0561 (4)
C70.08309 (9)0.48044 (14)0.13808 (11)0.0579 (4)
C80.04036 (11)0.52126 (17)0.17465 (15)0.0806 (6)
H8A0.02000.45690.18610.121*
H8B0.00260.57050.12720.121*
H8C0.07100.56260.23420.121*
C90.08394 (8)0.74903 (12)0.10862 (11)0.0544 (4)
C100.02085 (9)0.80650 (14)0.04547 (13)0.0674 (5)
H100.00700.78740.02010.081*
C110.00115 (10)0.89243 (16)0.07922 (15)0.0802 (5)
H110.04430.93010.03660.096*
C120.04032 (12)0.92210 (17)0.17508 (16)0.0879 (6)
H120.02590.98080.19750.105*
C130.10292 (13)0.86578 (19)0.23792 (15)0.0986 (7)
H130.13100.88610.30320.118*
C140.12486 (10)0.77844 (16)0.20507 (13)0.0816 (6)
H140.16740.73970.24840.098*
C150.17109 (8)0.25098 (12)0.11248 (11)0.0556 (4)
C160.18770 (10)0.22346 (14)0.04730 (13)0.0671 (4)
H160.17530.27280.00350.080*
C170.22302 (10)0.12162 (15)0.05848 (15)0.0779 (5)
H170.23520.10380.01570.093*
C180.24014 (10)0.04716 (15)0.13176 (17)0.0825 (6)
H180.26440.02030.13930.099*
C190.22130 (10)0.07272 (15)0.19354 (16)0.0809 (6)
H190.23100.02070.24150.097*
C200.18782 (9)0.17546 (15)0.18562 (14)0.0707 (5)
H200.17670.19320.22950.085*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0866 (10)0.0475 (7)0.0739 (9)0.0112 (7)0.0563 (9)0.0004 (6)
N20.0723 (9)0.0486 (7)0.0669 (8)0.0051 (6)0.0493 (7)0.0021 (6)
N30.0719 (9)0.0593 (8)0.0635 (8)0.0031 (7)0.0474 (7)0.0023 (6)
O10.0816 (9)0.0911 (9)0.0737 (8)0.0402 (7)0.0430 (7)0.0055 (6)
O20.0784 (8)0.0809 (8)0.0686 (8)0.0278 (7)0.0452 (7)0.0134 (6)
O30.1080 (10)0.0522 (6)0.0998 (9)0.0099 (6)0.0835 (9)0.0011 (6)
C10.0574 (9)0.0522 (9)0.0682 (10)0.0075 (7)0.0404 (9)0.0052 (7)
C20.0655 (10)0.0467 (8)0.0790 (11)0.0081 (7)0.0469 (9)0.0025 (7)
C30.0655 (10)0.0483 (9)0.0740 (11)0.0007 (7)0.0432 (9)0.0089 (7)
C40.0590 (9)0.0527 (8)0.0510 (8)0.0082 (7)0.0314 (8)0.0039 (6)
C50.0655 (10)0.0527 (8)0.0551 (9)0.0078 (7)0.0395 (8)0.0029 (7)
C60.0703 (10)0.0491 (8)0.0589 (9)0.0053 (7)0.0430 (9)0.0030 (7)
C70.0653 (10)0.0586 (9)0.0566 (9)0.0051 (8)0.0389 (8)0.0052 (7)
C80.0989 (14)0.0781 (12)0.0975 (14)0.0122 (11)0.0755 (13)0.0006 (10)
C90.0597 (9)0.0501 (8)0.0570 (9)0.0075 (7)0.0355 (8)0.0037 (7)
C100.0594 (10)0.0713 (10)0.0642 (10)0.0099 (8)0.0313 (9)0.0079 (8)
C110.0724 (12)0.0769 (12)0.0931 (14)0.0261 (10)0.0485 (11)0.0019 (10)
C120.1077 (16)0.0759 (12)0.0942 (15)0.0261 (12)0.0661 (14)0.0108 (11)
C130.1145 (17)0.1012 (16)0.0678 (12)0.0302 (14)0.0450 (13)0.0203 (11)
C140.0854 (13)0.0873 (13)0.0568 (10)0.0339 (11)0.0318 (10)0.0057 (9)
C150.0575 (9)0.0438 (8)0.0667 (10)0.0008 (7)0.0363 (8)0.0057 (7)
C160.0805 (12)0.0529 (9)0.0777 (11)0.0012 (8)0.0512 (10)0.0115 (8)
C170.0792 (12)0.0595 (11)0.1012 (14)0.0051 (9)0.0554 (12)0.0267 (10)
C180.0618 (11)0.0470 (10)0.1250 (17)0.0024 (8)0.0455 (12)0.0154 (11)
C190.0656 (11)0.0588 (10)0.1084 (16)0.0059 (9)0.0440 (11)0.0163 (10)
C200.0692 (11)0.0646 (10)0.0863 (13)0.0066 (9)0.0492 (10)0.0083 (9)
Geometric parameters (Å, º) top
N1—C41.317 (2)C8—H8C0.96
N1—C31.458 (2)C9—C141.372 (2)
N1—H10.913 (19)C9—C101.377 (2)
N2—C61.3797 (19)C10—C111.382 (2)
N2—N31.4016 (16)C10—H100.93
N2—C151.4175 (18)C11—C121.365 (3)
N3—C71.315 (2)C11—H110.93
O1—C11.1999 (18)C12—C131.363 (3)
O2—C11.317 (2)C12—H120.93
O2—H20.846 (9)C13—C141.384 (2)
O3—C61.2453 (18)C13—H130.93
C1—C21.503 (2)C14—H140.93
C2—C31.509 (2)C15—C201.379 (2)
C2—H2A0.97C15—C161.386 (2)
C2—H2B0.97C16—C171.390 (2)
C3—H3A0.97C16—H160.93
C3—H3B0.97C17—C181.370 (3)
C4—C51.406 (2)C17—H170.93
C4—C91.4929 (19)C18—C191.365 (3)
C5—C71.422 (2)C18—H180.93
C5—C61.4421 (19)C19—C201.389 (2)
C7—C81.496 (2)C19—H190.93
C8—H8A0.96C20—H200.93
C8—H8B0.96
C4—N1—C3127.81 (13)H8A—C8—H8C109.5
C4—N1—H1116.3 (11)H8B—C8—H8C109.5
C3—N1—H1115.2 (11)C14—C9—C10119.33 (14)
C6—N2—N3111.20 (11)C14—C9—C4119.42 (14)
C6—N2—C15127.70 (12)C10—C9—C4121.19 (14)
N3—N2—C15120.62 (12)C9—C10—C11120.22 (16)
C7—N3—N2107.05 (12)C9—C10—H10119.9
C1—O2—H2109.8 (17)C11—C10—H10119.9
O1—C1—O2123.30 (15)C12—C11—C10120.06 (17)
O1—C1—C2123.61 (16)C12—C11—H11120.0
O2—C1—C2113.09 (13)C10—C11—H11120.0
C1—C2—C3112.65 (13)C13—C12—C11120.01 (16)
C1—C2—H2A109.1C13—C12—H12120.0
C3—C2—H2A109.1C11—C12—H12120.0
C1—C2—H2B109.1C12—C13—C14120.34 (18)
C3—C2—H2B109.1C12—C13—H13119.8
H2A—C2—H2B107.8C14—C13—H13119.8
N1—C3—C2111.58 (13)C9—C14—C13120.02 (17)
N1—C3—H3A109.3C9—C14—H14120.0
C2—C3—H3A109.3C13—C14—H14120.0
N1—C3—H3B109.3C20—C15—C16119.61 (15)
C2—C3—H3B109.3C20—C15—N2120.20 (14)
H3A—C3—H3B108.0C16—C15—N2120.19 (14)
N1—C4—C5118.43 (13)C15—C16—C17119.46 (17)
N1—C4—C9118.60 (14)C15—C16—H16120.3
C5—C4—C9122.93 (14)C17—C16—H16120.3
C4—C5—C7132.45 (13)C18—C17—C16120.78 (18)
C4—C5—C6121.36 (14)C18—C17—H17119.6
C7—C5—C6105.95 (13)C16—C17—H17119.6
O3—C6—N2125.62 (13)C19—C18—C17119.50 (17)
O3—C6—C5129.57 (14)C19—C18—H18120.2
N2—C6—C5104.79 (12)C17—C18—H18120.2
N3—C7—C5111.01 (13)C18—C19—C20120.78 (19)
N3—C7—C8119.07 (15)C18—C19—H19119.6
C5—C7—C8129.92 (15)C20—C19—H19119.6
C7—C8—H8A109.5C15—C20—C19119.79 (18)
C7—C8—H8B109.5C15—C20—H20120.1
H8A—C8—H8B109.5C19—C20—H20120.1
C7—C8—H8C109.5
C6—N2—N3—C70.31 (18)C6—C5—C7—C8178.44 (17)
C15—N2—N3—C7172.93 (13)N1—C4—C9—C14102.9 (2)
O1—C1—C2—C38.0 (2)C5—C4—C9—C1474.6 (2)
O2—C1—C2—C3171.71 (14)N1—C4—C9—C1074.3 (2)
C4—N1—C3—C2115.01 (18)C5—C4—C9—C10108.09 (19)
C1—C2—C3—N161.02 (18)C14—C9—C10—C110.4 (3)
C3—N1—C4—C5173.33 (15)C4—C9—C10—C11177.72 (16)
C3—N1—C4—C94.4 (3)C9—C10—C11—C121.2 (3)
N1—C4—C5—C7178.91 (16)C10—C11—C12—C131.0 (3)
C9—C4—C5—C73.5 (3)C11—C12—C13—C140.1 (4)
N1—C4—C5—C67.5 (2)C10—C9—C14—C130.6 (3)
C9—C4—C5—C6170.06 (14)C4—C9—C14—C13176.78 (19)
N3—N2—C6—O3178.42 (15)C12—C13—C14—C90.7 (4)
C15—N2—C6—O36.5 (3)C6—N2—C15—C20149.17 (17)
N3—N2—C6—C50.04 (17)N3—N2—C15—C2022.1 (2)
C15—N2—C6—C5171.93 (14)C6—N2—C15—C1629.8 (2)
C4—C5—C6—O33.6 (3)N3—N2—C15—C16158.93 (15)
C7—C5—C6—O3178.63 (17)C20—C15—C16—C172.0 (3)
C4—C5—C6—N2174.73 (14)N2—C15—C16—C17176.96 (15)
C7—C5—C6—N20.34 (17)C15—C16—C17—C181.5 (3)
N2—N3—C7—C50.53 (18)C16—C17—C18—C191.0 (3)
N2—N3—C7—C8178.59 (15)C17—C18—C19—C202.8 (3)
C4—C5—C7—N3173.73 (17)C16—C15—C20—C190.2 (3)
C6—C5—C7—N30.56 (18)N2—C15—C20—C19178.79 (15)
C4—C5—C7—C87.3 (3)C18—C19—C20—C152.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.91 (2)2.46 (2)2.931 (2)112 (1)
N1—H1···O30.91 (2)1.93 (2)2.693 (2)140 (2)
O2—H2···N3i0.85 (3)1.85 (3)2.696 (2)177 (3)
C2—H2A···O2ii0.972.523.414 (3)153
C3—H3A···O1iii0.972.463.421 (3)169
C16—H16···O30.932.402.926 (2)115
C20—H20···O2iv0.932.583.377 (3)144
Symmetry codes: (i) x, y+1, z1/2; (ii) x, y, z1/2; (iii) x+1/2, y+3/2, z; (iv) x, y+1, z+1/2.
 

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