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In the crystal structure of the title compound, C20H21N3O, intra­molecular C—H...N hydrogen bonds stabilize the conformation of the mol­ecule.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806011548/sj2030sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806011548/sj2030Isup2.hkl
Contains datablock I

CCDC reference: 608489

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.056
  • wR factor = 0.169
  • Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C19'
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.68 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.20 Ratio PLAT301_ALERT_3_C Main Residue Disorder ......................... 17.00 Perc. PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C1 -C6 1.37 Ang. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 35.20 Deg. N3 -C16 -N3' 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 6 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 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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, 2001); 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: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2001).

4-Benzylidene-2-diethylamino-1-phenyl-1H-imidazol-5(4H)-one top
Crystal data top
C20H21N3ODx = 1.196 Mg m3
Mr = 319.40Melting point: 397 K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 7824 reflections
a = 18.8275 (10) Åθ = 2.2–21.6°
b = 8.9784 (5) ŵ = 0.08 mm1
c = 20.9951 (11) ÅT = 292 K
V = 3549.0 (3) Å3Block, yellow
Z = 80.30 × 0.30 × 0.20 mm
F(000) = 1360
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
4072 independent reflections
Radiation source: fine-focus sealed tube2667 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
φ and ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 2423
Tmin = 0.978, Tmax = 0.985k = 1111
28769 measured reflectionsl = 2727
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0794P)2 + 0.4215P]
where P = (Fo2 + 2Fc2)/3
4072 reflections(Δ/σ)max < 0.001
243 parametersΔρmax = 0.28 e Å3
10 restraintsΔρmin = 0.21 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*/UeqOcc. (<1)
C10.16661 (11)0.6943 (2)0.01515 (9)0.0781 (5)
H10.21530.69190.02270.094*
C20.14114 (14)0.7319 (3)0.04409 (10)0.0918 (7)
H20.17290.75520.07660.110*
C30.07034 (15)0.7355 (3)0.05568 (10)0.0960 (7)
H30.05350.76040.09590.115*
C40.02387 (14)0.7022 (4)0.00762 (13)0.1096 (8)
H40.02480.70580.01510.132*
C50.04899 (13)0.6635 (3)0.05181 (11)0.0942 (7)
H50.01740.63960.08430.113*
C60.11990 (11)0.6604 (2)0.06274 (8)0.0655 (5)
C70.16761 (9)0.4748 (2)0.13789 (8)0.0639 (4)
C80.16445 (9)0.46497 (18)0.20838 (7)0.0597 (4)
C90.18344 (9)0.34197 (19)0.24010 (8)0.0623 (4)
H90.20360.26750.21520.075*
C100.17737 (9)0.30692 (19)0.30742 (8)0.0606 (4)
C110.20343 (10)0.1706 (2)0.32901 (9)0.0751 (5)
H110.22640.10740.30060.090*
C120.19574 (12)0.1282 (3)0.39153 (11)0.0898 (7)
H120.21340.03670.40500.108*
C130.16219 (11)0.2202 (3)0.43434 (10)0.0877 (7)
H130.15650.19100.47650.105*
C140.13723 (11)0.3559 (3)0.41403 (9)0.0829 (6)
H140.11510.41930.44290.099*
C150.14447 (10)0.3993 (2)0.35153 (8)0.0712 (5)
H150.12710.49160.33870.085*
C160.13139 (11)0.6864 (2)0.18347 (8)0.0706 (5)
N30.11360 (13)0.8312 (2)0.18796 (8)0.0653 (6)0.829 (4)
C170.09128 (14)0.8842 (3)0.25103 (12)0.0789 (8)0.829 (4)
H17A0.09520.99190.25230.095*0.829 (4)
H17B0.12310.84400.28300.095*0.829 (4)
C180.01696 (18)0.8409 (5)0.26720 (18)0.1171 (13)0.829 (4)
H18A0.01450.87430.23420.176*0.829 (4)
H18B0.00360.88610.30690.176*0.829 (4)
H18C0.01400.73460.27100.176*0.829 (4)
C190.14025 (14)0.9465 (3)0.14407 (13)0.0782 (8)0.829 (4)
H19A0.16720.89880.11040.094*0.829 (4)
H19B0.17231.01170.16710.094*0.829 (4)
C200.0825 (2)1.0383 (4)0.11481 (16)0.1107 (11)0.829 (4)
H20A0.05260.97570.08930.166*0.829 (4)
H20B0.10321.11440.08850.166*0.829 (4)
H20C0.05471.08380.14790.166*0.829 (4)
N3'0.0728 (6)0.7922 (12)0.1823 (5)0.082 (3)*0.171 (4)
C17'0.0271 (9)0.837 (2)0.2393 (7)0.100 (6)*0.171 (4)
H17C0.01340.89310.22430.120*0.171 (4)
H17D0.00940.74720.25980.120*0.171 (4)
C18'0.0673 (12)0.928 (2)0.2872 (9)0.132 (7)*0.171 (4)
H18D0.11160.88020.29680.199*0.171 (4)
H18E0.03960.93700.32540.199*0.171 (4)
H18F0.07621.02530.27000.199*0.171 (4)
C19'0.0687 (6)0.9230 (12)0.1365 (5)0.076 (4)*0.171 (4)
H19C0.05100.88560.09620.091*0.171 (4)
H19D0.03340.99170.15280.091*0.171 (4)
C20'0.1346 (12)1.011 (3)0.1229 (14)0.160 (11)*0.171 (4)
H20D0.15171.05510.16160.240*0.171 (4)
H20E0.12411.08780.09260.240*0.171 (4)
H20F0.17040.94610.10570.240*0.171 (4)
N10.14591 (9)0.61920 (16)0.12467 (6)0.0690 (4)
N20.14019 (9)0.59921 (16)0.23248 (6)0.0684 (4)
O10.18357 (8)0.38233 (16)0.09851 (6)0.0857 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0856 (13)0.0868 (13)0.0618 (11)0.0005 (10)0.0080 (9)0.0089 (10)
C20.1122 (18)0.1026 (17)0.0605 (12)0.0081 (14)0.0169 (11)0.0163 (11)
C30.122 (2)0.1033 (17)0.0630 (12)0.0131 (15)0.0111 (12)0.0087 (11)
C40.0894 (16)0.140 (2)0.0994 (18)0.0065 (15)0.0121 (14)0.0200 (16)
C50.0882 (15)0.1173 (19)0.0771 (14)0.0027 (13)0.0131 (11)0.0197 (13)
C60.0864 (13)0.0591 (10)0.0510 (9)0.0036 (9)0.0048 (8)0.0005 (7)
C70.0770 (11)0.0594 (10)0.0554 (9)0.0005 (8)0.0012 (8)0.0038 (8)
C80.0714 (10)0.0558 (9)0.0519 (9)0.0032 (8)0.0001 (7)0.0052 (7)
C90.0721 (10)0.0570 (9)0.0579 (9)0.0001 (8)0.0009 (8)0.0054 (8)
C100.0614 (9)0.0599 (10)0.0603 (9)0.0065 (8)0.0060 (7)0.0028 (8)
C110.0763 (12)0.0736 (12)0.0754 (12)0.0063 (9)0.0028 (9)0.0106 (10)
C120.0865 (14)0.0941 (15)0.0887 (14)0.0091 (12)0.0037 (12)0.0327 (12)
C130.0806 (13)0.1167 (18)0.0659 (12)0.0046 (13)0.0003 (10)0.0285 (12)
C140.0908 (14)0.0973 (15)0.0605 (11)0.0006 (12)0.0068 (9)0.0053 (11)
C150.0854 (13)0.0675 (11)0.0606 (10)0.0003 (9)0.0003 (9)0.0032 (9)
C160.0990 (14)0.0593 (10)0.0535 (9)0.0053 (9)0.0031 (9)0.0025 (8)
N30.0864 (15)0.0528 (10)0.0567 (10)0.0040 (9)0.0031 (9)0.0027 (8)
C170.104 (2)0.0689 (14)0.0638 (14)0.0217 (13)0.0056 (13)0.0115 (11)
C180.102 (2)0.164 (4)0.085 (2)0.026 (2)0.017 (2)0.009 (2)
C190.100 (2)0.0563 (14)0.0785 (16)0.0010 (12)0.0025 (13)0.0044 (13)
C200.143 (3)0.083 (2)0.106 (2)0.0206 (19)0.012 (2)0.0203 (16)
N10.1001 (11)0.0588 (9)0.0483 (8)0.0035 (7)0.0056 (7)0.0008 (6)
N20.0937 (11)0.0598 (9)0.0518 (8)0.0067 (7)0.0004 (7)0.0016 (6)
O10.1253 (12)0.0730 (9)0.0588 (7)0.0166 (8)0.0042 (7)0.0118 (6)
Geometric parameters (Å, º) top
C1—C61.365 (3)C16—N31.346 (3)
C1—C21.375 (3)C16—N11.401 (2)
C1!—H10.9300C16—N3'1.456 (7)
C2—C31.355 (3)N3—C171.469 (3)
C2—H20.9300N3—C191.474 (3)
C3—C41.368 (3)C17—C181.492 (4)
C3—H30.9300C17—H17A0.9700
C4—C51.379 (3)C17—H17B0.9700
C4—H40.9300C18—H18A0.9600
C5—C61.355 (3)C18—H18B0.9600
C5—H50.9300C18—H18C0.9600
C6—N11.438 (2)C19—C201.497 (4)
C7—O11.209 (2)C19—H19A0.9700
C7—N11.388 (2)C19—H19B0.9700
C7—C81.484 (2)C20—H20A0.9600
C8—C91.338 (2)C20—H20B0.9600
C8—N21.385 (2)C20—H20C0.9600
C9—C101.453 (2)N3'—C19'1.521 (8)
C9—H90.9300N3'—C17'1.525 (9)
C10—C151.389 (3)C17'—C18'1.503 (9)
C10—C111.394 (3)C17'—H17C0.9700
C11—C121.375 (3)C17'—H17D0.9700
C11—H110.9300C18'—H18D0.9600
C12—C131.374 (3)C18'—H18E0.9600
C12—H120.9300C18'—H18F0.9600
C13—C141.374 (3)C19'—C20'1.498 (9)
C13—H130.9300C19'—H19C0.9700
C14—C151.376 (3)C19'—H19D0.9700
C14—H140.9300C20'—H20D0.9600
C15—H150.9300C20'—H20E0.9600
C16—N21.304 (2)C20'—H20F0.9600
C6—C1—C2119.5 (2)N3—C16—N3'35.2 (5)
C6—C1—H1120.3N1—C16—N3'114.5 (5)
C2—C1—H1120.3C16—N3—C17116.59 (17)
C3—C2—C1120.7 (2)C16—N3—C19123.36 (18)
C3—C2—H2119.6C17—N3—C19115.69 (18)
C1—C2—H2119.6N3—C17—C18112.9 (3)
C2—C3—C4119.4 (2)N3—C17—H17A109.0
C2—C3—H3120.3C18—C17—H17A109.0
C4—C3—H3120.3N3—C17—H17B109.0
C3—C4—C5120.2 (2)C18—C17—H17B109.0
C3—C4—H4119.9H17A—C17—H17B107.8
C5—C4—H4119.9N3—C19—C20113.3 (3)
C6—C5—C4119.8 (2)N3—C19—H19A108.9
C6—C5—H5120.1C20—C19—H19A108.9
C4—C5—H5120.1N3—C19—H19B108.9
C5—C6—C1120.41 (18)C20—C19—H19B108.9
C5—C6—N1119.61 (17)H19A—C19—H19B107.7
C1—C6—N1119.98 (18)C16—N3'—C19'123.5 (8)
O1—C7—N1125.29 (16)C16—N3'—C17'125.8 (10)
O1—C7—C8130.62 (17)C19'—N3'—C17'105.4 (10)
N1—C7—C8104.07 (14)C18'—C17'—N3'112.6 (16)
C9—C8—N2128.66 (15)C18'—C17'—H17C109.1
C9—C8—C7122.31 (15)N3'—C17'—H17C109.1
N2—C8—C7109.03 (14)C18'—C17'—H17D109.1
C8—C9—C10129.94 (16)N3'—C17'—H17D109.1
C8—C9—H9115.0H17C—C17'—H17D107.8
C10—C9—H9115.0C17'—C18'—H18D109.5
C15—C10—C11117.67 (17)C17'—C18'—H18E109.5
C15—C10—C9123.67 (16)H18D—C18'—H18E109.5
C11—C10—C9118.61 (17)C17'—C18'—H18F109.5
C12—C11—C10121.1 (2)H18D—C18'—H18F109.5
C12—C11—H11119.4H18E—C18'—H18F109.5
C10—C11—H11119.4C20'—C19'—N3'119.1 (17)
C13—C12—C11120.4 (2)C20'—C19'—H19C107.6
C13—C12—H12119.8N3'—C19'—H19C107.6
C11—C12—H12119.8C20'—C19'—H19D107.6
C14—C13—C12119.16 (19)N3'—C19'—H19D107.6
C14—C13—H13120.4H19C—C19'—H19D107.0
C12—C13—H13120.4C19'—C20'—H20D109.5
C13—C14—C15120.9 (2)C19'—C20'—H20E109.5
C13—C14—H14119.5H20D—C20'—H20E109.5
C15—C14—H14119.5C19'—C20'—H20F109.5
C14—C15—C10120.72 (19)H20D—C20'—H20F109.5
C14—C15—H15119.6H20E—C20'—H20F109.5
C10—C15—H15119.6C7—N1—C16106.48 (13)
N2—C16—N3123.82 (16)C7—N1—C6121.44 (14)
N2—C16—N1114.33 (16)C16—N1—C6128.28 (15)
N3—C16—N1121.76 (16)C16—N2—C8106.04 (14)
N2—C16—N3'120.1 (4)
C6—C1—C2—C30.1 (4)C16—N3—C19—C20127.5 (3)
C1—C2—C3—C40.5 (4)C17—N3—C19—C2076.9 (3)
C2—C3—C4—C50.9 (4)N2—C16—N3'—C19'163.9 (9)
C3—C4—C5—C60.9 (4)N3—C16—N3'—C19'56.8 (10)
C4—C5—C6—C10.5 (4)N1—C16—N3'—C19'54.2 (13)
C4—C5—C6—N1179.7 (2)N2—C16—N3'—C17'13.4 (16)
C2—C1—C6—C50.1 (3)N3—C16—N3'—C17'93.7 (16)
C2—C1—C6—N1179.28 (19)N1—C16—N3'—C17'155.3 (12)
O1—C7—C8—C93.0 (3)C16—N3'—C17'—C18'70 (2)
N1—C7—C8—C9178.30 (17)C19'—N3'—C17'—C18'85.2 (18)
O1—C7—C8—N2177.4 (2)C16—N3'—C19'—C20'41 (2)
N1—C7—C8—N21.30 (19)C17'—N3'—C19'—C20'114.5 (19)
N2—C8—C9—C107.3 (3)O1—C7—N1—C16178.76 (19)
C7—C8—C9—C10173.20 (17)C8—C7—N1—C160.07 (19)
C8—C9—C10—C154.5 (3)O1—C7—N1—C619.0 (3)
C8—C9—C10—C11178.13 (19)C8—C7—N1—C6159.81 (16)
C15—C10—C11—C121.1 (3)N2—C16—N1—C71.3 (2)
C9—C10—C11—C12176.51 (18)N3—C16—N1—C7175.4 (2)
C10—C11—C12—C130.2 (3)N3'—C16—N1—C7145.4 (6)
C11—C12—C13—C140.8 (3)N2—C16—N1—C6156.59 (18)
C12—C13—C14—C151.0 (3)N3—C16—N1—C626.7 (3)
C13—C14—C15—C100.1 (3)N3'—C16—N1—C612.5 (6)
C11—C10—C15—C140.9 (3)C5—C6—N1—C796.6 (2)
C9—C10—C15—C14176.55 (18)C1—C6—N1—C782.6 (2)
N2—C16—N3—C1710.8 (3)C5—C6—N1—C1658.4 (3)
N1—C16—N3—C17172.8 (2)C1—C6—N1—C16122.5 (2)
N3'—C16—N3—C1784.7 (7)N3—C16—N2—C8174.5 (2)
N2—C16—N3—C19144.7 (2)N1—C16—N2—C82.1 (2)
N1—C16—N3—C1931.7 (3)N3'—C16—N2—C8144.0 (6)
N3'—C16—N3—C19119.8 (7)C9—C8—N2—C16177.51 (19)
C16—N3—C17—C1877.6 (3)C7—C8—N2—C162.1 (2)
C19—N3—C17—C18125.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15—H15···N20.932.443.078 (2)126
C19—H19A···N10.972.562.968 (3)105
 

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