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In the title compound, C19H15N3O3, the phthalimide group, dihydro­pyrazole ring and phenyl ring are all essentially planar. The dihedral angles between the phthalimide group and dihydro­pyrazole ring, and the phthalimide group and phenyl ring are 57.0 (2) and 46.3 (3)°, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806051221/bi2112sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806051221/bi2112Isup2.hkl
Contains datablock I

CCDC reference: 633621

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.044
  • wR factor = 0.115
  • Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 0 ALERT type 5 Informative message, check

Computing details top

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

2-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)isoindoline- 1,3-dione top
Crystal data top
C19H15N3O3F(000) = 696
Mr = 333.34Dx = 1.385 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2202 reflections
a = 13.960 (3) Åθ = 2.6–25.3°
b = 15.948 (3) ŵ = 0.10 mm1
c = 7.3536 (14) ÅT = 294 K
β = 102.358 (3)°Plate, light yellow
V = 1599.2 (5) Å30.22 × 0.18 × 0.12 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
3257 independent reflections
Radiation source: fine-focus sealed tube2109 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
φ and ω scansθmax = 26.4°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 1417
Tmin = 0.979, Tmax = 0.989k = 1619
8874 measured reflectionsl = 99
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.115 w = 1/[σ2(Fo2) + (0.0466P)2 + 0.256P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
3257 reflectionsΔρmax = 0.21 e Å3
229 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0184 (19)
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
O10.47674 (11)1.01034 (9)0.2643 (2)0.0586 (5)
O20.29512 (10)0.77655 (9)0.3215 (2)0.0497 (4)
O30.25841 (10)1.02652 (8)0.00198 (19)0.0453 (4)
N10.36465 (11)0.90664 (9)0.2936 (2)0.0365 (4)
N20.15678 (11)1.01867 (10)0.3929 (2)0.0376 (4)
N30.16770 (11)1.05624 (10)0.2242 (2)0.0355 (4)
C10.45564 (14)0.93728 (12)0.2673 (3)0.0398 (5)
C20.51515 (14)0.86205 (12)0.2503 (3)0.0357 (5)
C30.60901 (14)0.85588 (13)0.2212 (3)0.0447 (5)
H30.64520.90320.20510.054*
C40.64726 (15)0.77573 (14)0.2168 (3)0.0485 (6)
H40.71070.76950.19840.058*
C50.59415 (15)0.70527 (13)0.2390 (3)0.0443 (5)
H50.62210.65250.23560.053*
C60.49910 (14)0.71228 (12)0.2665 (3)0.0397 (5)
H60.46250.66500.28120.048*
C70.46085 (13)0.79139 (11)0.2714 (2)0.0329 (4)
C80.36298 (14)0.81844 (12)0.2982 (3)0.0354 (5)
C90.28485 (13)0.95968 (11)0.3049 (3)0.0333 (4)
C100.23440 (14)0.96299 (12)0.4422 (3)0.0368 (5)
C110.24133 (13)1.01562 (11)0.1571 (3)0.0346 (5)
C120.24996 (18)0.91581 (14)0.6196 (3)0.0574 (6)
H12A0.30150.87560.62350.086*
H12B0.19060.88720.62820.086*
H12C0.26790.95400.72210.086*
C130.13464 (17)1.07761 (14)0.5324 (3)0.0506 (6)
H13A0.14211.04960.65010.076*
H13B0.06851.09730.49340.076*
H13C0.17901.12430.54460.076*
C140.08869 (13)1.10141 (11)0.1132 (2)0.0319 (4)
C150.00758 (14)1.08803 (12)0.1255 (3)0.0382 (5)
H150.02251.04820.20760.046*
C160.08147 (15)1.13436 (13)0.0150 (3)0.0463 (5)
H160.14601.12710.02670.056*
C170.06075 (16)1.19123 (14)0.1125 (3)0.0506 (6)
H170.11091.22140.18820.061*
C180.03521 (17)1.20282 (13)0.1261 (3)0.0485 (6)
H180.04951.24020.21360.058*
C190.11032 (15)1.15983 (12)0.0119 (3)0.0400 (5)
H190.17511.16990.01870.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0584 (10)0.0292 (8)0.0913 (12)0.0027 (7)0.0230 (9)0.0018 (8)
O20.0374 (8)0.0383 (8)0.0747 (11)0.0059 (7)0.0152 (7)0.0030 (7)
O30.0532 (9)0.0482 (9)0.0399 (8)0.0046 (7)0.0219 (7)0.0046 (7)
N10.0356 (9)0.0284 (9)0.0465 (10)0.0027 (7)0.0107 (7)0.0012 (7)
N20.0473 (10)0.0382 (10)0.0301 (9)0.0098 (8)0.0143 (7)0.0047 (7)
N30.0402 (10)0.0377 (9)0.0311 (9)0.0078 (7)0.0136 (7)0.0056 (7)
C10.0425 (13)0.0318 (11)0.0457 (12)0.0006 (9)0.0110 (10)0.0007 (9)
C20.0357 (11)0.0335 (11)0.0382 (11)0.0013 (9)0.0086 (9)0.0015 (9)
C30.0427 (13)0.0400 (12)0.0536 (13)0.0038 (10)0.0149 (10)0.0050 (10)
C40.0374 (12)0.0559 (15)0.0551 (14)0.0085 (11)0.0161 (10)0.0049 (11)
C50.0462 (13)0.0376 (12)0.0482 (13)0.0127 (10)0.0083 (10)0.0006 (10)
C60.0402 (12)0.0326 (11)0.0441 (12)0.0004 (9)0.0042 (9)0.0012 (9)
C70.0351 (11)0.0309 (11)0.0319 (10)0.0027 (8)0.0052 (8)0.0018 (8)
C80.0368 (12)0.0310 (11)0.0368 (11)0.0006 (9)0.0044 (9)0.0021 (8)
C90.0359 (11)0.0288 (10)0.0353 (11)0.0041 (8)0.0076 (9)0.0016 (8)
C100.0432 (12)0.0323 (11)0.0342 (11)0.0054 (9)0.0068 (9)0.0001 (8)
C110.0375 (11)0.0314 (10)0.0364 (11)0.0025 (8)0.0113 (9)0.0036 (8)
C120.0810 (17)0.0533 (14)0.0397 (13)0.0219 (12)0.0171 (12)0.0125 (11)
C130.0633 (15)0.0540 (14)0.0366 (12)0.0170 (11)0.0154 (10)0.0034 (10)
C140.0369 (11)0.0278 (10)0.0310 (10)0.0019 (8)0.0070 (8)0.0022 (8)
C150.0408 (12)0.0350 (11)0.0394 (11)0.0050 (9)0.0095 (9)0.0010 (9)
C160.0337 (12)0.0491 (13)0.0536 (13)0.0021 (10)0.0035 (10)0.0078 (11)
C170.0479 (14)0.0489 (14)0.0481 (13)0.0078 (10)0.0054 (11)0.0025 (11)
C180.0594 (15)0.0408 (13)0.0439 (13)0.0020 (10)0.0081 (11)0.0116 (10)
C190.0418 (12)0.0366 (11)0.0418 (12)0.0009 (9)0.0096 (9)0.0041 (9)
Geometric parameters (Å, º) top
O1—C11.203 (2)C7—C81.485 (3)
O2—C81.201 (2)C9—C101.350 (3)
O3—C111.226 (2)C9—C111.437 (3)
N1—C81.407 (2)C10—C121.481 (3)
N1—C11.412 (2)C12—H12A0.960
N1—C91.415 (2)C12—H12B0.960
N2—C101.388 (2)C12—H12C0.960
N2—N31.415 (2)C13—H13A0.960
N2—C131.472 (2)C13—H13B0.960
N3—C111.392 (2)C13—H13C0.960
N3—C141.420 (2)C14—C151.383 (3)
C1—C21.480 (3)C14—C191.387 (3)
C2—C31.376 (3)C15—C161.383 (3)
C2—C71.385 (3)C15—H150.930
C3—C41.388 (3)C16—C171.379 (3)
C3—H30.930C16—H160.930
C4—C51.375 (3)C17—C181.377 (3)
C4—H40.930C17—H170.930
C5—C61.389 (3)C18—C191.377 (3)
C5—H50.930C18—H180.930
C6—C71.373 (2)C19—H190.930
C6—H60.930
C8—N1—C1111.66 (15)C9—C10—N2109.44 (16)
C8—N1—C9125.35 (15)C9—C10—C12129.57 (18)
C1—N1—C9122.93 (15)N2—C10—C12120.95 (17)
C10—N2—N3105.99 (14)O3—C11—N3124.68 (17)
C10—N2—C13119.67 (16)O3—C11—C9131.06 (18)
N3—N2—C13114.75 (15)N3—C11—C9104.21 (15)
C11—N3—N2109.88 (14)C10—C12—H12A109.5
C11—N3—C14125.04 (15)C10—C12—H12B109.5
N2—N3—C14120.17 (14)H12A—C12—H12B109.5
O1—C1—N1124.64 (18)C10—C12—H12C109.5
O1—C1—C2129.76 (18)H12A—C12—H12C109.5
N1—C1—C2105.59 (16)H12B—C12—H12C109.5
C3—C2—C7121.43 (18)N2—C13—H13A109.5
C3—C2—C1129.93 (18)N2—C13—H13B109.5
C7—C2—C1108.64 (16)H13A—C13—H13B109.5
C2—C3—C4116.95 (19)N2—C13—H13C109.5
C2—C3—H3121.5H13A—C13—H13C109.5
C4—C3—H3121.5H13B—C13—H13C109.5
C5—C4—C3122.00 (19)C15—C14—C19119.99 (17)
C5—C4—H4119.0C15—C14—N3122.01 (17)
C3—C4—H4119.0C19—C14—N3118.00 (16)
C4—C5—C6120.52 (19)C14—C15—C16119.47 (19)
C4—C5—H5119.7C14—C15—H15120.3
C6—C5—H5119.7C16—C15—H15120.3
C7—C6—C5117.81 (18)C17—C16—C15120.84 (19)
C7—C6—H6121.1C17—C16—H16119.6
C5—C6—H6121.1C15—C16—H16119.6
C6—C7—C2121.28 (17)C18—C17—C16119.1 (2)
C6—C7—C8130.09 (17)C18—C17—H17120.4
C2—C7—C8108.63 (16)C16—C17—H17120.4
O2—C8—N1125.25 (18)C17—C18—C19120.9 (2)
O2—C8—C7129.29 (18)C17—C18—H18119.5
N1—C8—C7105.46 (16)C19—C18—H18119.5
C10—C9—N1127.65 (17)C18—C19—C14119.55 (19)
C10—C9—C11109.74 (16)C18—C19—H19120.2
N1—C9—C11122.48 (16)C14—C19—H19120.2
C10—N2—N3—C118.8 (2)C1—N1—C9—C10125.4 (2)
C13—N2—N3—C11143.11 (17)C8—N1—C9—C11117.9 (2)
C10—N2—N3—C14165.16 (16)C1—N1—C9—C1159.1 (3)
C13—N2—N3—C1460.5 (2)N1—C9—C10—N2175.22 (17)
C8—N1—C1—O1177.5 (2)C11—C9—C10—N20.7 (2)
C9—N1—C1—O15.1 (3)N1—C9—C10—C122.7 (4)
C8—N1—C1—C21.2 (2)C11—C9—C10—C12178.6 (2)
C9—N1—C1—C2176.19 (16)N3—N2—C10—C95.7 (2)
O1—C1—C2—C32.2 (4)C13—N2—C10—C9137.31 (18)
N1—C1—C2—C3179.18 (19)N3—N2—C10—C12176.20 (18)
O1—C1—C2—C7177.0 (2)C13—N2—C10—C1244.6 (3)
N1—C1—C2—C71.6 (2)N2—N3—C11—O3169.63 (17)
C7—C2—C3—C41.0 (3)C14—N3—C11—O314.6 (3)
C1—C2—C3—C4178.13 (19)N2—N3—C11—C98.15 (19)
C2—C3—C4—C50.5 (3)C14—N3—C11—C9163.15 (17)
C3—C4—C5—C60.1 (3)C10—C9—C11—O3173.0 (2)
C4—C5—C6—C70.3 (3)N1—C9—C11—O33.2 (3)
C5—C6—C7—C20.2 (3)C10—C9—C11—N34.6 (2)
C5—C6—C7—C8179.99 (18)N1—C9—C11—N3179.22 (16)
C3—C2—C7—C60.9 (3)C11—N3—C14—C15130.3 (2)
C1—C2—C7—C6178.42 (18)N2—N3—C14—C1522.3 (3)
C3—C2—C7—C8179.30 (18)C11—N3—C14—C1949.0 (3)
C1—C2—C7—C81.4 (2)N2—N3—C14—C19158.34 (16)
C1—N1—C8—O2178.89 (19)C19—C14—C15—C161.2 (3)
C9—N1—C8—O23.8 (3)N3—C14—C15—C16179.49 (18)
C1—N1—C8—C70.4 (2)C14—C15—C16—C172.6 (3)
C9—N1—C8—C7176.93 (16)C15—C16—C17—C181.3 (3)
C6—C7—C8—O20.1 (3)C16—C17—C18—C191.4 (3)
C2—C7—C8—O2179.9 (2)C17—C18—C19—C142.7 (3)
C6—C7—C8—N1179.14 (19)C15—C14—C19—C181.4 (3)
C2—C7—C8—N10.7 (2)N3—C14—C19—C18177.91 (18)
C8—N1—C9—C1057.6 (3)
 

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