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In the title compound, C19H19N3O2, the 2-methoxy­phenyl ring is almost coplanar with the pyrazoline ring [dihedral angle 8.7 (4)°], while the phenyl ring forms a dihedral angle of 54.9 (2)° with the pyrazoline ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806054171/bi2117sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806054171/bi2117Isup2.hkl
Contains datablock I

CCDC reference: 633625

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.039
  • wR factor = 0.096
  • Data-to-parameter ratio = 8.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.01 From the CIF: _reflns_number_total 1761 Count of symmetry unique reflns 1761 Completeness (_total/calc) 100.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2001); 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, 2001); software used to prepare material for publication: SHELXTL.

4-[(2-Methoxybenzylidene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazolidin-3(2H)-one top
Crystal data top
C19H19N3O2F(000) = 680
Mr = 321.37Dx = 1.244 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1484 reflections
a = 6.841 (3) Åθ = 2.7–21.8°
b = 14.021 (6) ŵ = 0.08 mm1
c = 17.886 (8) ÅT = 298 K
V = 1715.6 (13) Å3Block, yellow
Z = 40.48 × 0.32 × 0.12 mm
Data collection top
Bruker SMART CCD
diffractometer
1761 independent reflections
Radiation source: fine-focus sealed tube1081 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
φ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 87
Tmin = 0.961, Tmax = 0.990k = 1616
8948 measured reflectionsl = 2113
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0269P)2 + 0.4536P]
where P = (Fo2 + 2Fc2)/3
1761 reflections(Δ/σ)max < 0.001
220 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = 0.13 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
N10.0054 (4)0.4880 (2)0.03294 (16)0.0556 (8)
N20.1758 (4)0.4385 (2)0.01076 (16)0.0556 (8)
N30.0170 (5)0.26648 (19)0.13701 (16)0.0520 (8)
O10.2640 (4)0.45152 (17)0.10595 (14)0.0661 (8)
O20.5231 (4)0.24268 (19)0.24855 (15)0.0723 (8)
C10.0999 (6)0.4304 (2)0.0830 (2)0.0508 (10)
C20.0216 (5)0.3487 (2)0.09611 (18)0.0456 (9)
C30.1871 (5)0.3584 (2)0.0539 (2)0.0486 (9)
C40.3431 (5)0.4977 (3)0.0100 (2)0.0769 (13)
H4A0.44780.45760.02710.115*
H4B0.30570.54060.04930.115*
H4C0.38570.53360.03260.115*
C50.3600 (5)0.2954 (3)0.0509 (2)0.0717 (12)
H5A0.33440.23830.07880.108*
H5B0.38760.27920.00020.108*
H5C0.47050.32790.07210.108*
C60.1777 (6)0.2586 (2)0.1731 (2)0.0510 (9)
H60.26410.30980.17410.061*
C70.2282 (5)0.1715 (3)0.2125 (2)0.0508 (10)
C80.4051 (6)0.1641 (3)0.2509 (2)0.0568 (10)
C90.4540 (6)0.0814 (3)0.2893 (2)0.0675 (12)
H90.57130.07750.31540.081*
C100.3272 (7)0.0054 (3)0.2882 (2)0.0795 (13)
H100.36100.05080.31270.095*
C110.1519 (7)0.0113 (3)0.2517 (2)0.0781 (13)
H110.06560.04000.25270.094*
C120.1034 (6)0.0931 (3)0.2134 (2)0.0660 (11)
H120.01460.09610.18770.079*
C130.6883 (6)0.2465 (3)0.2968 (3)0.0920 (15)
H13A0.64700.23590.34740.138*
H13B0.74900.30800.29290.138*
H13C0.78020.19800.28260.138*
C140.0883 (5)0.5496 (3)0.0192 (2)0.0546 (10)
C150.0874 (6)0.5304 (3)0.0948 (2)0.0720 (12)
H150.02250.47730.11350.086*
C160.1854 (8)0.5920 (4)0.1421 (3)0.0973 (16)
H160.18350.58120.19340.117*
C170.2856 (7)0.6690 (4)0.1140 (4)0.107 (2)
H170.35410.70900.14610.128*
C180.2845 (8)0.6868 (3)0.0390 (3)0.0976 (18)
H180.35110.73950.02020.117*
C190.1849 (6)0.6270 (3)0.0092 (3)0.0734 (12)
H190.18360.63920.06030.088*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0411 (17)0.0626 (18)0.063 (2)0.0002 (17)0.0141 (17)0.0094 (17)
N20.0404 (18)0.070 (2)0.056 (2)0.0017 (17)0.0113 (17)0.0035 (18)
N30.0529 (19)0.0488 (18)0.0544 (18)0.0066 (17)0.0019 (18)0.0016 (15)
O10.0461 (16)0.0685 (16)0.0835 (19)0.0045 (14)0.0220 (15)0.0099 (16)
O20.0611 (17)0.0758 (18)0.0800 (19)0.0018 (17)0.0181 (16)0.0173 (16)
C10.042 (2)0.055 (2)0.055 (2)0.009 (2)0.008 (2)0.002 (2)
C20.042 (2)0.048 (2)0.047 (2)0.0043 (19)0.003 (2)0.0050 (18)
C30.042 (2)0.054 (2)0.049 (2)0.002 (2)0.001 (2)0.006 (2)
C40.049 (2)0.096 (3)0.086 (3)0.019 (2)0.015 (2)0.020 (3)
C50.057 (3)0.086 (3)0.072 (3)0.018 (2)0.008 (2)0.005 (2)
C60.050 (2)0.051 (2)0.052 (2)0.007 (2)0.003 (2)0.0027 (19)
C70.055 (3)0.048 (2)0.049 (2)0.007 (2)0.000 (2)0.0004 (19)
C80.059 (3)0.055 (2)0.057 (2)0.010 (2)0.005 (2)0.006 (2)
C90.074 (3)0.069 (3)0.059 (2)0.013 (3)0.002 (2)0.009 (2)
C100.094 (4)0.064 (3)0.081 (3)0.014 (3)0.001 (3)0.020 (3)
C110.089 (3)0.059 (3)0.087 (3)0.006 (3)0.002 (3)0.015 (3)
C120.072 (3)0.061 (2)0.065 (3)0.001 (2)0.000 (3)0.007 (2)
C130.061 (3)0.098 (3)0.117 (4)0.002 (3)0.030 (3)0.023 (3)
C140.042 (2)0.054 (2)0.068 (3)0.005 (2)0.009 (2)0.013 (2)
C150.065 (3)0.084 (3)0.067 (3)0.002 (3)0.007 (2)0.012 (3)
C160.071 (3)0.134 (4)0.087 (4)0.004 (4)0.001 (3)0.045 (4)
C170.066 (4)0.113 (4)0.141 (6)0.012 (3)0.009 (4)0.065 (4)
C180.085 (4)0.075 (3)0.133 (5)0.014 (3)0.028 (4)0.034 (4)
C190.071 (3)0.060 (2)0.089 (3)0.004 (2)0.016 (3)0.009 (3)
Geometric parameters (Å, º) top
N1—C11.405 (4)C8—C91.388 (5)
N1—N21.413 (4)C9—C101.375 (5)
N1—C141.423 (4)C9—H90.930
N2—C31.365 (4)C10—C111.368 (5)
N2—C41.462 (4)C10—H100.930
N3—C61.280 (4)C11—C121.377 (5)
N3—C21.391 (4)C11—H110.930
O1—C11.231 (4)C12—H120.930
O2—C81.367 (4)C13—H13A0.960
O2—C131.423 (4)C13—H13B0.960
C1—C21.435 (5)C13—H13C0.960
C2—C31.368 (4)C14—C191.367 (5)
C3—C51.477 (5)C14—C151.379 (5)
C4—H4A0.960C15—C161.382 (5)
C4—H4B0.960C15—H150.930
C4—H4C0.960C16—C171.373 (6)
C5—H5A0.960C16—H160.930
C5—H5B0.960C17—C181.364 (7)
C5—H5C0.960C17—H170.930
C6—C71.452 (5)C18—C191.382 (6)
C6—H60.930C18—H180.930
C7—C121.392 (5)C19—H190.930
C7—C81.395 (5)
C1—N1—N2108.6 (3)C9—C8—C7121.0 (4)
C1—N1—C14122.4 (3)C10—C9—C8119.2 (4)
N2—N1—C14119.0 (3)C10—C9—H9120.4
C3—N2—N1107.0 (3)C8—C9—H9120.4
C3—N2—C4124.5 (3)C11—C10—C9120.9 (4)
N1—N2—C4116.0 (3)C11—C10—H10119.6
C6—N3—C2120.0 (3)C9—C10—H10119.6
C8—O2—C13118.7 (3)C10—C11—C12119.9 (4)
O1—C1—N1122.8 (3)C10—C11—H11120.1
O1—C1—C2131.7 (4)C12—C11—H11120.1
N1—C1—C2105.4 (3)C11—C12—C7121.1 (4)
C3—C2—N3122.0 (3)C11—C12—H12119.4
C3—C2—C1108.1 (3)C7—C12—H12119.4
N3—C2—C1129.7 (3)O2—C13—H13A109.5
N2—C3—C2110.2 (3)O2—C13—H13B109.5
N2—C3—C5121.1 (3)H13A—C13—H13B109.5
C2—C3—C5128.6 (3)O2—C13—H13C109.5
N2—C4—H4A109.5H13A—C13—H13C109.5
N2—C4—H4B109.5H13B—C13—H13C109.5
H4A—C4—H4B109.5C19—C14—C15121.3 (4)
N2—C4—H4C109.5C19—C14—N1117.1 (4)
H4A—C4—H4C109.5C15—C14—N1121.5 (4)
H4B—C4—H4C109.5C14—C15—C16118.4 (4)
C3—C5—H5A109.5C14—C15—H15120.8
C3—C5—H5B109.5C16—C15—H15120.8
H5A—C5—H5B109.5C17—C16—C15120.6 (5)
C3—C5—H5C109.5C17—C16—H16119.7
H5A—C5—H5C109.5C15—C16—H16119.7
H5B—C5—H5C109.5C18—C17—C16120.1 (5)
N3—C6—C7121.4 (4)C18—C17—H17120.0
N3—C6—H6119.3C16—C17—H17120.0
C7—C6—H6119.3C17—C18—C19120.2 (5)
C12—C7—C8117.9 (4)C17—C18—H18119.9
C12—C7—C6121.6 (3)C19—C18—H18119.9
C8—C7—C6120.5 (4)C14—C19—C18119.3 (4)
O2—C8—C9123.1 (4)C14—C19—H19120.4
O2—C8—C7115.9 (3)C18—C19—H19120.4
C1—N1—N2—C37.8 (4)C13—O2—C8—C910.4 (6)
C14—N1—N2—C3154.3 (3)C13—O2—C8—C7169.1 (4)
C1—N1—N2—C4151.7 (3)C12—C7—C8—O2179.9 (3)
C14—N1—N2—C461.8 (4)C6—C7—C8—O20.0 (5)
N2—N1—C1—O1172.9 (3)C12—C7—C8—C90.6 (6)
C14—N1—C1—O127.7 (5)C6—C7—C8—C9179.5 (4)
N2—N1—C1—C25.6 (4)O2—C8—C9—C10179.5 (4)
C14—N1—C1—C2150.7 (3)C7—C8—C9—C101.0 (6)
C6—N3—C2—C3176.8 (3)C8—C9—C10—C111.8 (7)
C6—N3—C2—C13.9 (5)C9—C10—C11—C122.0 (7)
O1—C1—C2—C3176.9 (4)C10—C11—C12—C71.5 (7)
N1—C1—C2—C31.4 (4)C8—C7—C12—C110.8 (6)
O1—C1—C2—N33.2 (7)C6—C7—C12—C11179.3 (4)
N1—C1—C2—N3175.1 (3)C1—N1—C14—C1968.7 (5)
N1—N2—C3—C27.0 (4)N2—N1—C14—C19149.6 (3)
C4—N2—C3—C2147.1 (3)C1—N1—C14—C15109.1 (4)
N1—N2—C3—C5173.3 (3)N2—N1—C14—C1532.6 (5)
C4—N2—C3—C533.2 (5)C19—C14—C15—C160.7 (6)
N3—C2—C3—N2170.8 (3)N1—C14—C15—C16178.4 (3)
C1—C2—C3—N23.5 (4)C14—C15—C16—C171.7 (7)
N3—C2—C3—C59.0 (6)C15—C16—C17—C181.8 (8)
C1—C2—C3—C5176.7 (4)C16—C17—C18—C190.8 (8)
C2—N3—C6—C7176.1 (3)C15—C14—C19—C180.3 (6)
N3—C6—C7—C120.6 (6)N1—C14—C19—C18177.5 (4)
N3—C6—C7—C8179.4 (3)C17—C18—C19—C140.2 (7)
 

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