Literature DB >> 22590225

4-[(4-Benzyl-oxybenzyl-idene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one.

Grzegorz Dutkiewicz, Divya N Shetty, B Narayana, H S Yathirajan, Maciej Kubicki.   

Abstract

In the title mol-ecule, C(25)H(23)N(3)O(2), two terminal phenyl rings are twisted by 50.20 (6) and 71.26 (5)° from the mean plane (r.m.s. deviation = 0.032 Å) of the central benzyl-idene-amino-pyrazolone fragment. The N atoms of the pyrazole ring have a pyramidal environment, the sums of the valence angles around them being 353.5 (2) and 347.3 (2)°. The crystal structure is stabilized by C-H⋯O interactions.

Entities:  

Year:  2012        PMID： 22590225      PMCID： PMC3344463          DOI： 10.1107/S1600536812014262

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

Related crystal structures have been described by Shi (2005 ▶), Jun (2005 ▶), Zhen et al. (2006 ▶), Liu et al. (2006 ▶), Diao & Chen (2006 ▶), Duan et al. (2006 ▶), Hu (2006 ▶) and Zhang et al. (2006 ▶).

Experimental

Crystal data

C25H23N3O2 M = 397.46 Monoclinic, a = 19.8137 (19) Å b = 6.1588 (4) Å c = 18.0784 (14) Å β = 108.881 (9)° V = 2087.4 (3) Å3 Z = 4 Mo Kα radiation μ = 0.08 mm−1 T = 295 K 0.5 × 0.4 × 0.2 mm

Data collection

Agilent Xcalibur Eos diffractometer Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.890, T max = 1.000 8408 measured reflections 4352 independent reflections 3298 reflections with I > 2σ(I) R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.052 wR(F 2) = 0.119 S = 1.04 4352 reflections 363 parameters All H-atom parameters refined Δρmax = 0.68 e Å−3 Δρmin = −0.22 e Å−3 Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812014262/cv5278sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014262/cv5278Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812014262/cv5278Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C25H23N3O2F(000) = 840
Mr = 397.46Dx = 1.265 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 19.8137 (19) ÅCell parameters from 2304 reflections
b = 6.1588 (4) Åθ = 3.1–28.2°
c = 18.0784 (14) ŵ = 0.08 mm−1
β = 108.881 (9)°T = 295 K
V = 2087.4 (3) Å3Block, yellow
Z = 40.5 × 0.4 × 0.2 mm
Agilent Xcalibur Eos diffractometer4352 independent reflections
Radiation source: Enhance (Mo) X-ray Source3298 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
Detector resolution: 16.1544 pixels mm-1θmax = 28.3°, θmin = 3.3°
ω–scanh = −25→26
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)k = −8→8
Tmin = 0.890, Tmax = 1.000l = −19→24
8408 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119All H-atom parameters refined
S = 1.04w = 1/[σ2(Fo2) + (0.0411P)2 + 1.0652P] where P = (Fo2 + 2Fc2)/3
4352 reflections(Δ/σ)max = 0.001
363 parametersΔρmax = 0.68 e Å−3
0 restraintsΔρmin = −0.22 e Å−3
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.
xyzUiso*/Ueq
N10.77141 (7)1.0983 (2)1.10006 (8)0.0236 (3)
C110.83244 (8)1.0018 (3)1.15422 (9)0.0213 (4)
C120.88429 (10)0.9158 (3)1.12682 (11)0.0278 (4)
H120.8798 (9)0.924 (3)1.0744 (11)0.027 (5)*
C130.94283 (10)0.8168 (3)1.17855 (12)0.0334 (5)
H130.9787 (11)0.760 (3)1.1597 (11)0.037 (6)*
C140.95142 (10)0.8101 (3)1.25755 (12)0.0354 (5)
H140.9920 (11)0.744 (3)1.2934 (11)0.035 (5)*
C150.90004 (10)0.8993 (3)1.28475 (11)0.0310 (4)
H150.9032 (10)0.893 (3)1.3398 (12)0.039 (6)*
C160.83978 (9)0.9942 (3)1.23326 (10)0.0253 (4)
H160.8016 (9)1.053 (3)1.2519 (10)0.024 (5)*
N20.73781 (8)1.2714 (2)1.12442 (8)0.0253 (3)
C210.78145 (11)1.4594 (3)1.15796 (13)0.0324 (5)
H21A0.7554 (12)1.554 (4)1.1837 (13)0.052 (7)*
H21B0.8227 (12)1.412 (4)1.1980 (13)0.049 (6)*
H21C0.7936 (13)1.536 (4)1.1174 (16)0.070 (8)*
C30.67109 (9)1.2867 (3)1.07207 (10)0.0261 (4)
C310.62346 (11)1.4701 (4)1.07381 (14)0.0364 (5)
H31A0.6409 (11)1.606 (4)1.0604 (12)0.045 (6)*
H31B0.6190 (12)1.488 (4)1.1266 (15)0.059 (7)*
H31C0.5748 (13)1.442 (4)1.0366 (14)0.061 (7)*
C40.65791 (9)1.1164 (3)1.02127 (10)0.0258 (4)
C50.72166 (9)0.9880 (3)1.03848 (9)0.0242 (4)
O50.73457 (7)0.8174 (2)1.01041 (7)0.0324 (3)
N410.59094 (8)1.0843 (3)0.96662 (8)0.0289 (4)
C420.57671 (10)0.9211 (4)0.92063 (10)0.0306 (4)
H420.6106 (11)0.804 (3)0.9202 (11)0.038 (6)*
C430.50516 (9)0.8971 (4)0.86385 (10)0.0311 (5)
C440.48958 (11)0.7305 (4)0.80983 (11)0.0407 (5)
H440.5249 (11)0.619 (4)0.8114 (12)0.042 (6)*
C450.42241 (11)0.7081 (4)0.75510 (12)0.0443 (6)
H450.4146 (11)0.584 (4)0.7209 (13)0.047 (6)*
C460.36996 (9)0.8553 (4)0.75447 (10)0.0372 (5)
C470.38462 (10)1.0237 (4)0.80834 (11)0.0363 (5)
H470.3460 (11)1.129 (3)0.8060 (11)0.039 (6)*
C480.45139 (10)1.0441 (4)0.86208 (11)0.0343 (5)
H480.4620 (10)1.163 (3)0.8994 (12)0.036 (6)*
O490.30121 (7)0.8475 (3)0.70470 (7)0.0454 (4)
C500.28438 (11)0.6850 (5)0.64450 (13)0.0495 (7)
H50A0.3121 (13)0.719 (4)0.6121 (14)0.059 (7)*
H50B0.2951 (15)0.526 (5)0.6720 (16)0.087 (10)*
C510.20732 (10)0.7172 (4)0.59813 (10)0.0356 (5)
C520.18548 (12)0.8875 (4)0.54645 (12)0.0459 (6)
H520.2206 (13)0.984 (4)0.5387 (14)0.069 (8)*
C530.11413 (13)0.9177 (4)0.50569 (13)0.0480 (6)
H530.0951 (13)1.038 (5)0.4697 (15)0.073 (8)*
C540.06391 (11)0.7793 (4)0.51715 (13)0.0403 (5)
H540.0139 (12)0.805 (4)0.4887 (13)0.045 (6)*
C550.08516 (11)0.6104 (4)0.56866 (12)0.0368 (5)
H550.0505 (11)0.512 (4)0.5780 (12)0.047 (6)*
C560.15672 (11)0.5793 (4)0.60880 (11)0.0360 (5)
H560.1712 (11)0.459 (4)0.6452 (13)0.045 (6)*
U11U22U33U12U13U23
N10.0250 (8)0.0217 (8)0.0205 (7)−0.0004 (6)0.0022 (6)−0.0013 (6)
C110.0207 (8)0.0171 (8)0.0230 (8)−0.0054 (7)0.0027 (7)−0.0011 (7)
C120.0282 (10)0.0270 (10)0.0288 (10)−0.0068 (8)0.0099 (8)−0.0026 (8)
C130.0263 (10)0.0276 (11)0.0466 (12)−0.0013 (9)0.0121 (9)−0.0051 (9)
C140.0260 (10)0.0271 (11)0.0423 (11)0.0014 (9)−0.0040 (9)0.0022 (9)
C150.0354 (10)0.0262 (10)0.0248 (9)−0.0038 (9)0.0007 (8)0.0010 (8)
C160.0273 (9)0.0235 (9)0.0230 (9)−0.0036 (8)0.0055 (7)−0.0024 (8)
N20.0257 (8)0.0187 (8)0.0274 (8)−0.0009 (6)0.0028 (6)−0.0006 (6)
C210.0316 (11)0.0235 (10)0.0345 (11)−0.0049 (9)0.0000 (9)−0.0040 (9)
C30.0232 (9)0.0269 (10)0.0257 (9)−0.0030 (8)0.0045 (7)0.0087 (8)
C310.0297 (11)0.0307 (12)0.0442 (13)0.0013 (9)0.0059 (9)0.0048 (10)
C40.0241 (9)0.0312 (10)0.0200 (8)−0.0064 (8)0.0045 (7)0.0041 (8)
C50.0277 (9)0.0252 (10)0.0184 (8)−0.0062 (8)0.0058 (7)0.0022 (8)
O50.0351 (7)0.0317 (8)0.0270 (7)−0.0036 (6)0.0053 (6)−0.0081 (6)
N410.0250 (8)0.0400 (10)0.0193 (7)−0.0085 (7)0.0040 (6)0.0046 (7)
C420.0276 (10)0.0412 (12)0.0221 (9)−0.0072 (9)0.0070 (8)0.0005 (9)
C430.0239 (9)0.0498 (13)0.0199 (8)−0.0091 (9)0.0073 (7)−0.0022 (9)
C440.0275 (10)0.0617 (15)0.0317 (11)−0.0018 (11)0.0077 (9)−0.0130 (11)
C450.0269 (10)0.0733 (17)0.0316 (11)−0.0055 (11)0.0079 (9)−0.0244 (12)
C460.0208 (9)0.0693 (15)0.0210 (9)−0.0081 (10)0.0062 (7)−0.0108 (10)
C470.0241 (10)0.0583 (15)0.0260 (9)−0.0020 (10)0.0075 (8)−0.0067 (10)
C480.0290 (10)0.0492 (14)0.0243 (9)−0.0082 (9)0.0079 (8)−0.0082 (9)
O490.0205 (7)0.0846 (12)0.0287 (7)−0.0030 (7)0.0046 (6)−0.0241 (8)
C500.0243 (10)0.089 (2)0.0322 (11)−0.0042 (12)0.0047 (9)−0.0266 (13)
C510.0268 (10)0.0596 (14)0.0192 (9)−0.0038 (10)0.0059 (8)−0.0132 (10)
C520.0427 (13)0.0631 (16)0.0343 (11)−0.0225 (12)0.0159 (10)−0.0083 (11)
C530.0551 (15)0.0474 (14)0.0331 (11)−0.0063 (12)0.0027 (10)0.0021 (11)
C540.0274 (11)0.0427 (13)0.0414 (12)−0.0007 (10)−0.0018 (9)−0.0124 (10)
C550.0294 (10)0.0384 (12)0.0412 (11)−0.0091 (10)0.0097 (9)−0.0098 (10)
C560.0347 (11)0.0425 (13)0.0278 (10)−0.0020 (10)0.0059 (8)−0.0056 (10)
N1—C51.401 (2)C42—C431.464 (2)
N1—N21.401 (2)C42—H420.99 (2)
N1—C111.417 (2)C43—C441.381 (3)
C11—C121.382 (2)C43—C481.390 (3)
C11—C161.389 (2)C44—C451.385 (3)
C12—C131.375 (3)C44—H440.98 (2)
C12—H120.924 (18)C45—C461.376 (3)
C13—C141.383 (3)C45—H450.96 (2)
C13—H130.95 (2)C46—O491.369 (2)
C14—C151.380 (3)C46—C471.387 (3)
C14—H140.95 (2)C47—C481.370 (3)
C15—C161.384 (3)C47—H470.99 (2)
C15—H150.98 (2)C48—H480.97 (2)
C16—H160.990 (18)O49—C501.436 (3)
N2—C31.357 (2)C50—C511.498 (3)
N2—C211.455 (2)C50—H50A0.95 (2)
C21—H21A0.99 (2)C50—H50B1.09 (3)
C21—H21B0.94 (2)C51—C561.375 (3)
C21—H21C0.97 (3)C51—C521.378 (3)
C3—C41.363 (3)C52—C531.379 (3)
C3—C311.479 (3)C52—H520.96 (3)
C31—H31A0.97 (2)C53—C541.376 (3)
C31—H31B0.99 (2)C53—H530.98 (3)
C31—H31C1.00 (3)C54—C551.369 (3)
C4—N411.388 (2)C54—H540.97 (2)
C4—C51.436 (3)C55—C561.381 (3)
C5—O51.229 (2)C55—H550.97 (2)
N41—C421.276 (2)C56—H560.97 (2)
C5—N1—N2109.57 (13)N41—C42—C43119.73 (19)
C5—N1—C11124.71 (15)N41—C42—H42125.0 (12)
N2—N1—C11119.21 (13)C43—C42—H42115.3 (12)
C12—C11—C16120.85 (16)C44—C43—C48118.24 (18)
C12—C11—N1118.70 (15)C44—C43—C42121.00 (19)
C16—C11—N1120.45 (15)C48—C43—C42120.75 (18)
C13—C12—C11119.18 (18)C43—C44—C45121.5 (2)
C13—C12—H12120.2 (11)C43—C44—H44120.7 (13)
C11—C12—H12120.6 (11)C45—C44—H44117.7 (13)
C12—C13—C14120.70 (19)C46—C45—C44119.3 (2)
C12—C13—H13119.1 (12)C46—C45—H45123.6 (13)
C14—C13—H13120.2 (12)C44—C45—H45117.1 (13)
C15—C14—C13119.85 (18)O49—C46—C45124.78 (19)
C15—C14—H14119.2 (12)O49—C46—C47115.17 (18)
C13—C14—H14120.9 (12)C45—C46—C47120.03 (18)
C14—C15—C16120.26 (18)C48—C47—C46120.1 (2)
C14—C15—H15122.5 (12)C48—C47—H47121.6 (12)
C16—C15—H15117.2 (12)C46—C47—H47118.3 (12)
C15—C16—C11119.12 (17)C47—C48—C43120.9 (2)
C15—C16—H16120.9 (10)C47—C48—H48120.2 (12)
C11—C16—H16120.0 (10)C43—C48—H48118.9 (12)
C3—N2—N1106.76 (14)C46—O49—C50117.40 (16)
C3—N2—C21123.27 (16)O49—C50—C51106.06 (18)
N1—N2—C21117.24 (15)O49—C50—H50A106.2 (16)
N2—C21—H21A109.6 (13)C51—C50—H50A108.4 (15)
N2—C21—H21B108.9 (14)O49—C50—H50B108.6 (15)
H21A—C21—H21B106.0 (18)C51—C50—H50B112.8 (15)
N2—C21—H21C109.5 (16)H50A—C50—H50B114 (2)
H21A—C21—H21C111 (2)C56—C51—C52118.83 (19)
H21B—C21—H21C111 (2)C56—C51—C50119.8 (2)
N2—C3—C4110.33 (16)C52—C51—C50121.3 (2)
N2—C3—C31121.50 (17)C51—C52—C53120.5 (2)
C4—C3—C31128.17 (17)C51—C52—H52119.2 (15)
C3—C31—H31A111.9 (13)C53—C52—H52120.3 (15)
C3—C31—H31B111.1 (14)C54—C53—C52120.1 (2)
H31A—C31—H31B107.3 (19)C54—C53—H53115.4 (15)
C3—C31—H31C109.6 (14)C52—C53—H53124.4 (16)
H31A—C31—H31C109.3 (19)C55—C54—C53119.7 (2)
H31B—C31—H31C107.5 (18)C55—C54—H54121.5 (13)
C3—C4—N41121.31 (17)C53—C54—H54118.8 (13)
C3—C4—C5108.33 (15)C54—C55—C56120.0 (2)
N41—C4—C5130.32 (17)C54—C55—H55121.0 (13)
O5—C5—N1123.76 (16)C56—C55—H55119.0 (13)
O5—C5—C4131.83 (16)C51—C56—C55120.8 (2)
N1—C5—C4104.39 (15)C51—C56—H56119.8 (13)
C42—N41—C4122.30 (17)C55—C56—H56119.4 (13)
C5—N1—C11—C1262.7 (2)C3—C4—C5—N1−1.39 (18)
N2—N1—C11—C12−148.63 (16)N41—C4—C5—N1−178.76 (17)
C5—N1—C11—C16−117.28 (19)C3—C4—N41—C42−177.14 (17)
N2—N1—C11—C1631.4 (2)C5—C4—N41—C42−0.1 (3)
C16—C11—C12—C131.7 (3)C4—N41—C42—C43−179.59 (16)
N1—C11—C12—C13−178.33 (17)N41—C42—C43—C44175.54 (18)
C11—C12—C13—C14−2.5 (3)N41—C42—C43—C48−3.3 (3)
C12—C13—C14—C151.5 (3)C48—C43—C44—C45−0.1 (3)
C13—C14—C15—C160.4 (3)C42—C43—C44—C45−179.0 (2)
C14—C15—C16—C11−1.2 (3)C43—C44—C45—C460.0 (3)
C12—C11—C16—C150.1 (3)C44—C45—C46—O49−178.3 (2)
N1—C11—C16—C15−179.87 (16)C44—C45—C46—C47−0.1 (3)
C5—N1—N2—C3−8.15 (18)O49—C46—C47—C48178.61 (18)
C11—N1—N2—C3−161.16 (15)C45—C46—C47—C480.2 (3)
C5—N1—N2—C21−151.23 (16)C46—C47—C48—C43−0.3 (3)
C11—N1—N2—C2155.8 (2)C44—C43—C48—C470.2 (3)
N1—N2—C3—C47.24 (19)C42—C43—C48—C47179.14 (18)
C21—N2—C3—C4147.53 (18)C45—C46—O49—C50−5.7 (3)
N1—N2—C3—C31−172.05 (16)C47—C46—O49—C50176.0 (2)
C21—N2—C3—C31−31.8 (3)C46—O49—C50—C51−178.53 (18)
N2—C3—C4—N41173.97 (15)O49—C50—C51—C56−103.0 (3)
C31—C3—C4—N41−6.8 (3)O49—C50—C51—C5274.8 (3)
N2—C3—C4—C5−3.7 (2)C56—C51—C52—C53−0.6 (3)
C31—C3—C4—C5175.55 (18)C50—C51—C52—C53−178.4 (2)
N2—N1—C5—O5−172.94 (15)C51—C52—C53—C540.9 (3)
C11—N1—C5—O5−21.7 (3)C52—C53—C54—C55−0.6 (3)
N2—N1—C5—C45.81 (17)C53—C54—C55—C56−0.1 (3)
C11—N1—C5—C4157.01 (15)C52—C51—C56—C55−0.1 (3)
C3—C4—C5—O5177.22 (18)C50—C51—C56—C55177.76 (19)
N41—C4—C5—O5−0.2 (3)C54—C55—C56—C510.4 (3)
D—H···AD—HH···AD···AD—H···A
C16—H16···O49i0.990 (18)2.486 (18)3.470 (2)172.6 (15)
C21—H21C···O5ii0.97 (3)2.58 (3)3.352 (3)137.3 (19)
C31—H31A···O5ii0.97 (2)2.65 (2)3.517 (3)149.1 (17)
C52—H52···O5iii0.96 (3)2.51 (3)3.411 (3)156 (2)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C16—H16⋯O49i0.990 (18)2.486 (18)3.470 (2)172.6 (15)
C21—H21C⋯O5ii0.97 (3)2.58 (3)3.352 (3)137.3 (19)
C31—H31A⋯O5ii0.97 (2)2.65 (2)3.517 (3)149.1 (17)
C52—H52⋯O5iii0.96 (3)2.51 (3)3.411 (3)156 (2)

Symmetry codes: (i) ; (ii) ; (iii) .

  1 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290
  1 in total
  1 in total

1.  A second monoclinic polymorph of 4-[(E)-(4-benzyl-oxybenzyl-idene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one.

Authors:  Rajni Kant; Vivek K Gupta; Kamini Kapoor; Prakash S Nayak; B K Sarojini; B Narayana
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-12-19
  1 in total

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