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In the title compound, C19H19N3O, the five-membered imidazolone ring is essentially planar, and the packing of the mol­ecules in the crystal structure is mainly due to inter­molecular N—H...O hydrogen-bonding inter­actions, which link the mol­ecules into chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806042541/bx2029sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806042541/bx2029Isup2.hkl
Contains datablock I

CCDC reference: 627365

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.049
  • wR factor = 0.148
  • Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17
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 0 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

4-Benzylidene-2-(isopropylamino)-1-phenyl-imidazolin-5(4H)-one ? top
Crystal data top
C19H19N3OF(000) = 648
Mr = 305.37Dx = 1.207 Mg m3
Monoclinic, P21/cMelting point: 397 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 12.1186 (15) ÅCell parameters from 3899 reflections
b = 10.8172 (13) Åθ = 2.4–27.3°
c = 12.8606 (16) ŵ = 0.08 mm1
β = 94.880 (2)°T = 292 K
V = 1679.8 (4) Å3Block, colorless
Z = 40.20 × 0.20 × 0.18 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2818 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 27.5°, θmin = 2.5°
φ and ω scansh = 1514
9888 measured reflectionsk = 1311
3792 independent reflectionsl = 1616
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.0778P)2 + 0.0795P]
where P = (Fo2 + 2Fc2)/3
3792 reflections(Δ/σ)max < 0.001
213 parametersΔρmax = 0.16 e Å3
1 restraintΔρmin = 0.21 e Å3
Special details top

Experimental. Spectroscopic analysis:1H NMR (CDCl3, 200 MHz): 1.34 (d, 6H, 2CH3, J=6.2 Hz), 4.38–4.54 (m, 2H, NCH and NH), 6.84(s, 1H, =CH), 7.29–8.20 (m, 10H, Ar—H). MS (EI 70 eV) m/z(%): 305 (M+, 93), 290 (36), 263 (90), 119 (100).

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
C10.03441 (14)0.28283 (15)0.81601 (15)0.0745 (5)
H10.00700.21280.79720.089*
C20.01716 (17)0.38882 (19)0.84717 (16)0.0896 (6)
H20.09360.38970.85030.107*
C30.04344 (19)0.49204 (17)0.87340 (13)0.0836 (6)
H30.00830.56360.89340.100*
C40.1555 (2)0.49031 (16)0.87028 (15)0.0877 (6)
H40.19660.56090.88820.105*
C50.20847 (15)0.38490 (14)0.84090 (13)0.0719 (4)
H50.28510.38360.83990.086*
C60.14701 (12)0.28188 (11)0.81311 (10)0.0511 (3)
C70.23724 (12)0.15769 (12)0.67941 (11)0.0544 (3)
C80.28817 (11)0.03249 (12)0.68559 (10)0.0501 (3)
C90.22442 (10)0.06460 (11)0.83421 (10)0.0488 (3)
C100.34003 (11)0.01458 (13)0.60627 (11)0.0554 (3)
H100.33770.03430.54660.066*
C110.39925 (11)0.13090 (13)0.60019 (11)0.0568 (4)
C120.41650 (14)0.21285 (15)0.68313 (14)0.0716 (4)
H120.38850.19460.74650.086*
C130.47498 (16)0.32140 (18)0.67250 (16)0.0869 (6)
H130.48570.37560.72860.104*
C140.51727 (14)0.34963 (19)0.57949 (17)0.0844 (6)
H140.55640.42270.57280.101*
C150.50171 (15)0.27007 (18)0.49670 (17)0.0820 (5)
H150.53030.28900.43380.098*
C160.44358 (13)0.16183 (16)0.50681 (13)0.0692 (4)
H160.43360.10820.45030.083*
C170.21249 (14)0.06243 (12)0.99001 (12)0.0615 (4)
H170.28780.09140.98160.074*
C180.2032 (2)0.03674 (17)1.10370 (14)0.0931 (6)
H18A0.25930.02141.12840.140*
H18B0.21300.11231.14260.140*
H18C0.13140.00291.11280.140*
C190.1325 (2)0.16079 (18)0.94959 (16)0.0991 (7)
H19A0.05820.13390.95730.149*
H19B0.14700.23560.98850.149*
H19C0.14130.17570.87720.149*
N10.20119 (9)0.17406 (10)0.77834 (9)0.0529 (3)
N20.27473 (9)0.01924 (10)0.78325 (9)0.0515 (3)
N30.19461 (11)0.05313 (10)0.93133 (9)0.0586 (3)
H3A0.1738 (13)0.1174 (11)0.9644 (12)0.070*
O10.22715 (11)0.23147 (10)0.60850 (9)0.0771 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0709 (10)0.0632 (10)0.0909 (12)0.0117 (8)0.0148 (9)0.0013 (8)
C20.0832 (12)0.0892 (14)0.0993 (14)0.0374 (11)0.0251 (10)0.0135 (11)
C30.1309 (17)0.0676 (11)0.0536 (9)0.0471 (12)0.0145 (10)0.0012 (8)
C40.1233 (17)0.0573 (10)0.0807 (13)0.0151 (10)0.0024 (11)0.0197 (8)
C50.0807 (11)0.0585 (9)0.0757 (11)0.0055 (8)0.0018 (8)0.0139 (8)
C60.0687 (8)0.0438 (7)0.0418 (7)0.0115 (6)0.0107 (6)0.0035 (5)
C70.0661 (8)0.0457 (7)0.0532 (8)0.0003 (6)0.0158 (6)0.0012 (6)
C80.0539 (7)0.0443 (7)0.0532 (8)0.0024 (5)0.0102 (6)0.0036 (5)
C90.0544 (7)0.0412 (6)0.0518 (7)0.0024 (5)0.0109 (6)0.0011 (5)
C100.0602 (8)0.0528 (8)0.0544 (8)0.0019 (6)0.0122 (6)0.0049 (6)
C110.0512 (7)0.0566 (8)0.0631 (9)0.0008 (6)0.0081 (6)0.0139 (7)
C120.0753 (10)0.0723 (10)0.0670 (10)0.0197 (8)0.0050 (8)0.0095 (8)
C130.0894 (12)0.0811 (12)0.0876 (13)0.0306 (10)0.0067 (10)0.0103 (10)
C140.0664 (10)0.0783 (12)0.1070 (15)0.0228 (9)0.0025 (10)0.0316 (11)
C150.0685 (10)0.0887 (13)0.0910 (13)0.0076 (9)0.0195 (9)0.0342 (11)
C160.0672 (9)0.0698 (10)0.0732 (10)0.0012 (7)0.0201 (8)0.0163 (8)
C170.0817 (10)0.0463 (8)0.0585 (9)0.0128 (7)0.0169 (7)0.0079 (6)
C180.1551 (19)0.0665 (10)0.0598 (10)0.0169 (11)0.0203 (11)0.0114 (8)
C190.1454 (19)0.0665 (11)0.0858 (13)0.0240 (12)0.0126 (12)0.0133 (9)
N10.0673 (7)0.0416 (6)0.0517 (6)0.0078 (5)0.0157 (5)0.0020 (5)
N20.0580 (6)0.0435 (6)0.0542 (7)0.0023 (5)0.0122 (5)0.0025 (5)
N30.0804 (8)0.0419 (6)0.0559 (7)0.0124 (5)0.0199 (6)0.0039 (5)
O10.1175 (9)0.0571 (6)0.0602 (7)0.0151 (6)0.0282 (6)0.0112 (5)
Geometric parameters (Å, º) top
C1—C61.368 (2)C11—C121.389 (2)
C1—C21.381 (2)C11—C161.397 (2)
C1—H10.9300C12—C131.384 (2)
C2—C31.363 (3)C12—H120.9300
C2—H20.9300C13—C141.375 (3)
C3—C41.362 (3)C13—H130.9300
C3—H30.9300C14—C151.370 (3)
C4—C51.377 (2)C14—H140.9300
C4—H40.9300C15—C161.378 (2)
C5—C61.371 (2)C15—H150.9300
C5—H50.9300C16—H160.9300
C6—N11.4288 (16)C17—N31.4667 (18)
C7—O11.2102 (16)C17—C191.502 (3)
C7—N11.3913 (17)C17—C181.502 (2)
C7—C81.4876 (19)C17—H170.9800
C8—C101.3431 (19)C18—H18A0.9600
C8—N21.3970 (17)C18—H18B0.9600
C9—N21.3007 (16)C18—H18C0.9600
C9—N31.3352 (17)C19—H19A0.9600
C9—N11.4010 (17)C19—H19B0.9600
C10—C111.454 (2)C19—H19C0.9600
C10—H100.9300N3—H3A0.863 (9)
C6—C1—C2119.41 (17)C14—C13—H13119.8
C6—C1—H1120.3C12—C13—H13119.8
C2—C1—H1120.3C15—C14—C13119.99 (16)
C3—C2—C1120.28 (18)C15—C14—H14120.0
C3—C2—H2119.9C13—C14—H14120.0
C1—C2—H2119.9C14—C15—C16119.87 (17)
C4—C3—C2119.94 (16)C14—C15—H15120.1
C4—C3—H3120.0C16—C15—H15120.1
C2—C3—H3120.0C15—C16—C11121.43 (17)
C3—C4—C5120.58 (18)C15—C16—H16119.3
C3—C4—H4119.7C11—C16—H16119.3
C5—C4—H4119.7N3—C17—C19111.29 (14)
C6—C5—C4119.27 (17)N3—C17—C18108.85 (12)
C6—C5—H5120.4C19—C17—C18111.62 (15)
C4—C5—H5120.4N3—C17—H17108.3
C1—C6—C5120.52 (13)C19—C17—H17108.3
C1—C6—N1120.04 (13)C18—C17—H17108.3
C5—C6—N1119.42 (13)C17—C18—H18A109.5
O1—C7—N1125.85 (12)C17—C18—H18B109.5
O1—C7—C8130.96 (13)H18A—C18—H18B109.5
N1—C7—C8103.19 (11)C17—C18—H18C109.5
C10—C8—N2128.96 (13)H18A—C18—H18C109.5
C10—C8—C7121.56 (13)H18B—C18—H18C109.5
N2—C8—C7109.46 (11)C17—C19—H19A109.5
N2—C9—N3125.61 (12)C17—C19—H19B109.5
N2—C9—N1114.40 (11)H19A—C19—H19B109.5
N3—C9—N1119.98 (11)C17—C19—H19C109.5
C8—C10—C11129.34 (14)H19A—C19—H19C109.5
C8—C10—H10115.3H19B—C19—H19C109.5
C11—C10—H10115.3C7—N1—C9107.24 (10)
C12—C11—C16117.61 (14)C7—N1—C6125.35 (10)
C12—C11—C10123.62 (13)C9—N1—C6127.37 (10)
C16—C11—C10118.75 (14)C9—N2—C8105.62 (11)
C13—C12—C11120.69 (16)C9—N3—C17121.37 (11)
C13—C12—H12119.7C9—N3—H3A120.0 (11)
C11—C12—H12119.7C17—N3—H3A118.0 (11)
C14—C13—C12120.40 (19)
C6—C1—C2—C30.9 (3)C12—C11—C16—C150.5 (2)
C1—C2—C3—C40.9 (3)C10—C11—C16—C15179.20 (15)
C2—C3—C4—C50.1 (3)O1—C7—N1—C9177.19 (15)
C3—C4—C5—C61.0 (3)C8—C7—N1—C92.86 (14)
C2—C1—C6—C50.1 (2)O1—C7—N1—C60.7 (2)
C2—C1—C6—N1178.30 (15)C8—C7—N1—C6179.24 (12)
C4—C5—C6—C11.0 (2)N2—C9—N1—C72.08 (16)
C4—C5—C6—N1177.36 (15)N3—C9—N1—C7177.63 (12)
O1—C7—C8—C104.5 (2)N2—C9—N1—C6179.92 (12)
N1—C7—C8—C10175.49 (13)N3—C9—N1—C60.2 (2)
O1—C7—C8—N2177.14 (16)C1—C6—N1—C7100.42 (17)
N1—C7—C8—N22.92 (14)C5—C6—N1—C777.95 (18)
N2—C8—C10—C111.8 (2)C1—C6—N1—C977.06 (19)
C7—C8—C10—C11176.31 (13)C5—C6—N1—C9104.57 (17)
C8—C10—C11—C123.5 (2)N3—C9—N2—C8179.55 (13)
C8—C10—C11—C16177.81 (14)N1—C9—N2—C80.13 (15)
C16—C11—C12—C130.4 (2)C10—C8—N2—C9176.50 (14)
C10—C11—C12—C13179.11 (15)C7—C8—N2—C91.75 (14)
C11—C12—C13—C140.2 (3)N2—C9—N3—C172.9 (2)
C12—C13—C14—C150.0 (3)N1—C9—N3—C17176.80 (13)
C13—C14—C15—C160.0 (3)C19—C17—N3—C973.26 (19)
C14—C15—C16—C110.2 (3)C18—C17—N3—C9163.31 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···N20.932.423.0614 (19)127
N3—H3A···O1i0.86 (1)2.52 (1)3.2593 (16)145 (1)
Symmetry code: (i) x, y+1/2, z+1/2.
 

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