4-(4-Methoxy­benzyl­idene)-2-(4-morpholino)-1-phenyl-1H-imidazol-5(4H)-one

In the title compound, C₂₁H₂₁N₃O₃, the five-membered imidazolone ring is planar. The packing of the mol­ecules in the crystal structure is mainly due to inter­molecular C—H...O hydrogen-bonding inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.049
• wR factor = 0.134
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level C
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) ...       3.10 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   1 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

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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.

4-(4-Methoxybenzylidene)-2-(4-morpholino)-1-phenyl-1H-imidazol-5(4H)-one

Crystal data

C21H21N3O3	Z = 2
Mr = 363.41	F(000) = 384
Triclinic, P1	Dx = 1.301 Mg m^−3
Hall symbol: -P 1	Melting point: 495 K
a = 7.6366 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6475 (12) Å	Cell parameters from 4642 reflections
c = 12.8267 (14) Å	θ = 2.3–28.0°
α = 69.167 (2)°	µ = 0.09 mm^−1
β = 76.885 (2)°	T = 292 K
γ = 74.118 (2)°	Block, colourless
V = 927.76 (18) Å^3	0.40 × 0.30 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3378 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.063
Graphite monochromator	θmax = 27.5°, θmin = 1.7°
φ and ω scans	h = −9→9
10789 measured reflections	k = −13→13
4200 independent reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.134	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0698P)^2 + 0.0643P] where P = (Fo^2 + 2Fc^2)/3
4200 reflections	(Δ/σ)max < 0.001
245 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

Experimental. ¹H NMR (CDCl₃, 200 MHz): δ 3.29 (t, 4H, 2NCH₂, J=4.4 Hz), 3.62 (t, 4H, 2OCH₂, J = 4.8 Hz), 3.81 (s, 3H, OCH₃), 6.82 (s, 1H, ═CH), 6.87–8.06 (m, 9H, Ar—H). MS (EI 70 eV) m/z (%): 363 (M⁺).

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.0803 (4)	−0.2535 (2)	0.99727 (17)	0.1016 (8)
H1A	0.0756	−0.1933	1.0390	0.152*
H1B	0.1039	−0.3472	1.0453	0.152*
H1C	−0.0353	−0.2326	0.9705	0.152*
C2	0.2162 (2)	−0.10722 (14)	0.82787 (12)	0.0493 (3)
C3	0.0688 (2)	0.00350 (15)	0.82453 (13)	0.0540 (4)
H3	−0.0346	−0.0050	0.8791	0.065*
C4	0.3703 (2)	−0.09259 (14)	0.74624 (13)	0.0527 (4)
H4	0.4689	−0.1670	0.7478	0.063*
C5	0.37780 (18)	0.03029 (14)	0.66376 (12)	0.0480 (3)
H5	0.4824	0.0386	0.6102	0.058*
C6	0.07656 (18)	0.12644 (14)	0.73979 (12)	0.0489 (3)
H6	−0.0242	0.1996	0.7369	0.059*
C7	0.23080 (17)	0.14415 (13)	0.65837 (10)	0.0400 (3)
C8	0.23122 (17)	0.27764 (13)	0.57353 (11)	0.0408 (3)
H8	0.1183	0.3394	0.5711	0.049*
C9	0.37081 (16)	0.32537 (12)	0.49780 (10)	0.0384 (3)
C10	0.34143 (16)	0.46474 (13)	0.41658 (11)	0.0396 (3)
C11	0.53447 (17)	0.57578 (13)	0.24429 (11)	0.0411 (3)
C12	0.4920 (2)	0.71292 (14)	0.23712 (13)	0.0541 (4)
H12	0.4557	0.7390	0.3020	0.065*
C13	0.5040 (3)	0.81049 (17)	0.13251 (16)	0.0759 (5)
H13	0.4764	0.9031	0.1269	0.091*
C14	0.5561 (3)	0.7727 (2)	0.03642 (16)	0.0806 (6)
H14	0.5642	0.8395	−0.0339	0.097*
C15	0.5963 (3)	0.6363 (2)	0.04418 (13)	0.0710 (5)
H15	0.6308	0.6110	−0.0211	0.085*
C16	0.5860 (2)	0.53644 (16)	0.14820 (12)	0.0533 (4)
H16	0.6133	0.4439	0.1535	0.064*
C17	0.63413 (16)	0.34835 (13)	0.39752 (10)	0.0379 (3)
C18	0.92086 (17)	0.43237 (14)	0.31931 (12)	0.0461 (3)
H18A	0.9533	0.4399	0.3854	0.055*
H18B	0.8470	0.5201	0.2813	0.055*
C19	1.0920 (2)	0.39704 (17)	0.24170 (13)	0.0575 (4)
H19A	1.0583	0.3946	0.1741	0.069*
H19B	1.1625	0.4679	0.2197	0.069*
C20	0.92593 (19)	0.18941 (15)	0.40534 (13)	0.0556 (4)
H20A	0.8575	0.1187	0.4209	0.067*
H20B	0.9549	0.1864	0.4761	0.067*
C21	1.1004 (2)	0.16360 (17)	0.32657 (17)	0.0696 (5)
H21A	1.1773	0.0766	0.3632	0.083*
H21B	1.0702	0.1559	0.2599	0.083*
N1	0.51511 (14)	0.47450 (10)	0.35266 (9)	0.0400 (3)
N2	0.55637 (13)	0.26088 (10)	0.48154 (9)	0.0403 (3)
N3	0.81521 (14)	0.32430 (11)	0.35324 (9)	0.0427 (3)
O1	0.22165 (17)	−0.23495 (11)	0.90508 (10)	0.0684 (3)
O2	0.20335 (12)	0.55464 (10)	0.40076 (9)	0.0540 (3)
O3	1.20159 (13)	0.26901 (12)	0.29320 (10)	0.0678 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.125 (2)	0.0648 (12)	0.0754 (13)	−0.0220 (12)	0.0256 (13)	0.0015 (10)
C2	0.0517 (8)	0.0407 (7)	0.0522 (8)	−0.0100 (6)	−0.0065 (6)	−0.0111 (6)
C3	0.0457 (8)	0.0509 (8)	0.0560 (8)	−0.0113 (6)	0.0099 (6)	−0.0155 (7)
C4	0.0412 (7)	0.0426 (7)	0.0659 (9)	−0.0005 (6)	−0.0066 (6)	−0.0140 (7)
C5	0.0320 (7)	0.0475 (8)	0.0585 (8)	−0.0051 (5)	0.0010 (6)	−0.0166 (6)
C6	0.0370 (7)	0.0429 (7)	0.0580 (8)	−0.0030 (5)	0.0030 (6)	−0.0154 (6)
C7	0.0319 (6)	0.0410 (7)	0.0462 (7)	−0.0065 (5)	−0.0029 (5)	−0.0151 (5)
C8	0.0296 (6)	0.0416 (7)	0.0487 (7)	−0.0038 (5)	−0.0042 (5)	−0.0150 (6)
C9	0.0297 (6)	0.0407 (7)	0.0431 (6)	−0.0045 (5)	−0.0051 (5)	−0.0132 (5)
C10	0.0281 (6)	0.0419 (7)	0.0472 (7)	−0.0048 (5)	−0.0041 (5)	−0.0148 (6)
C11	0.0306 (6)	0.0423 (7)	0.0457 (7)	−0.0071 (5)	−0.0075 (5)	−0.0075 (5)
C12	0.0577 (9)	0.0442 (8)	0.0589 (8)	−0.0089 (6)	−0.0162 (7)	−0.0110 (7)
C13	0.0957 (15)	0.0455 (9)	0.0779 (12)	−0.0166 (9)	−0.0286 (11)	0.0020 (8)
C14	0.0918 (14)	0.0726 (12)	0.0595 (11)	−0.0236 (10)	−0.0206 (9)	0.0112 (9)
C15	0.0701 (11)	0.0890 (13)	0.0474 (9)	−0.0158 (9)	−0.0063 (8)	−0.0158 (8)
C16	0.0491 (8)	0.0558 (8)	0.0519 (8)	−0.0083 (6)	−0.0052 (6)	−0.0167 (7)
C17	0.0297 (6)	0.0395 (6)	0.0421 (6)	−0.0035 (5)	−0.0062 (5)	−0.0122 (5)
C18	0.0321 (6)	0.0504 (8)	0.0529 (8)	−0.0089 (5)	−0.0027 (5)	−0.0147 (6)
C19	0.0374 (7)	0.0727 (10)	0.0572 (9)	−0.0149 (7)	0.0033 (6)	−0.0180 (8)
C20	0.0347 (7)	0.0479 (8)	0.0694 (9)	0.0018 (6)	−0.0085 (6)	−0.0083 (7)
C21	0.0393 (8)	0.0610 (10)	0.0978 (13)	0.0052 (7)	−0.0031 (8)	−0.0282 (9)
N1	0.0297 (5)	0.0383 (6)	0.0449 (6)	−0.0035 (4)	−0.0037 (4)	−0.0084 (5)
N2	0.0291 (5)	0.0414 (6)	0.0452 (6)	−0.0045 (4)	−0.0038 (4)	−0.0106 (5)
N3	0.0276 (5)	0.0423 (6)	0.0506 (6)	−0.0029 (4)	−0.0025 (4)	−0.0107 (5)
O1	0.0757 (8)	0.0449 (6)	0.0673 (7)	−0.0114 (5)	−0.0010 (6)	−0.0038 (5)
O2	0.0308 (5)	0.0457 (5)	0.0706 (6)	0.0005 (4)	−0.0029 (4)	−0.0097 (5)
O3	0.0302 (5)	0.0764 (8)	0.0877 (8)	−0.0030 (5)	0.0013 (5)	−0.0271 (6)

Geometric parameters (Å, º)

C1—O1	1.405 (2)	C12—H12	0.9300
C1—H1A	0.9600	C13—C14	1.372 (3)
C1—H1B	0.9600	C13—H13	0.9300
C1—H1C	0.9600	C14—C15	1.371 (3)
C2—O1	1.3645 (17)	C14—H14	0.9300
C2—C3	1.385 (2)	C15—C16	1.381 (2)
C2—C4	1.389 (2)	C15—H15	0.9300
C3—C6	1.378 (2)	C16—H16	0.9300
C3—H3	0.9300	C17—N2	1.2961 (16)
C4—C5	1.3651 (19)	C17—N3	1.3614 (16)
C4—H4	0.9300	C17—N1	1.4074 (15)
C5—C7	1.4020 (17)	C18—N3	1.4687 (17)
C5—H5	0.9300	C18—C19	1.4992 (19)
C6—C7	1.3918 (18)	C18—H18A	0.9700
C6—H6	0.9300	C18—H18B	0.9700
C7—C8	1.4509 (18)	C19—O3	1.4075 (19)
C8—C9	1.3467 (18)	C19—H19A	0.9700
C8—H8	0.9300	C19—H19B	0.9700
C9—N2	1.3994 (15)	C20—N3	1.4606 (17)
C9—C10	1.4703 (17)	C20—C21	1.503 (2)
C10—O2	1.2148 (14)	C20—H20A	0.9700
C10—N1	1.4012 (15)	C20—H20B	0.9700
C11—C12	1.3801 (19)	C21—O3	1.422 (2)
C11—C16	1.3807 (19)	C21—H21A	0.9700
C11—N1	1.4299 (16)	C21—H21B	0.9700
C12—C13	1.376 (2)
O1—C1—H1A	109.5	C13—C14—H14	120.1
O1—C1—H1B	109.5	C14—C15—C16	120.46 (17)
H1A—C1—H1B	109.5	C14—C15—H15	119.8
O1—C1—H1C	109.5	C16—C15—H15	119.8
H1A—C1—H1C	109.5	C11—C16—C15	119.08 (15)
H1B—C1—H1C	109.5	C11—C16—H16	120.5
O1—C2—C3	124.79 (13)	C15—C16—H16	120.5
O1—C2—C4	115.62 (12)	N2—C17—N3	124.55 (11)
C3—C2—C4	119.57 (13)	N2—C17—N1	114.53 (10)
C6—C3—C2	119.53 (13)	N3—C17—N1	120.92 (11)
C6—C3—H3	120.2	N3—C18—C19	109.17 (11)
C2—C3—H3	120.2	N3—C18—H18A	109.8
C5—C4—C2	120.44 (13)	C19—C18—H18A	109.8
C5—C4—H4	119.8	N3—C18—H18B	109.8
C2—C4—H4	119.8	C19—C18—H18B	109.8
C4—C5—C7	121.23 (13)	H18A—C18—H18B	108.3
C4—C5—H5	119.4	O3—C19—C18	111.58 (12)
C7—C5—H5	119.4	O3—C19—H19A	109.3
C3—C6—C7	121.88 (12)	C18—C19—H19A	109.3
C3—C6—H6	119.1	O3—C19—H19B	109.3
C7—C6—H6	119.1	C18—C19—H19B	109.3
C6—C7—C5	117.33 (12)	H19A—C19—H19B	108.0
C6—C7—C8	118.85 (11)	N3—C20—C21	109.09 (13)
C5—C7—C8	123.82 (12)	N3—C20—H20A	109.9
C9—C8—C7	129.63 (12)	C21—C20—H20A	109.9
C9—C8—H8	115.2	N3—C20—H20B	109.9
C7—C8—H8	115.2	C21—C20—H20B	109.9
C8—C9—N2	129.46 (12)	H20A—C20—H20B	108.3
C8—C9—C10	121.18 (11)	O3—C21—C20	113.05 (13)
N2—C9—C10	109.36 (10)	O3—C21—H21A	109.0
O2—C10—N1	124.60 (12)	C20—C21—H21A	109.0
O2—C10—C9	131.31 (11)	O3—C21—H21B	109.0
N1—C10—C9	104.05 (10)	C20—C21—H21B	109.0
C12—C11—C16	120.79 (13)	H21A—C21—H21B	107.8
C12—C11—N1	119.11 (12)	C10—N1—C17	106.18 (10)
C16—C11—N1	120.02 (12)	C10—N1—C11	120.99 (10)
C13—C12—C11	119.02 (15)	C17—N1—C11	129.60 (10)
C13—C12—H12	120.5	C17—N2—C9	105.86 (10)
C11—C12—H12	120.5	C17—N3—C20	116.42 (11)
C14—C13—C12	120.77 (17)	C17—N3—C18	120.46 (10)
C14—C13—H13	119.6	C20—N3—C18	111.25 (10)
C12—C13—H13	119.6	C2—O1—C1	118.70 (13)
C15—C14—C13	119.88 (16)	C19—O3—C21	110.22 (11)
C15—C14—H14	120.1
O1—C2—C3—C6	−177.59 (14)	O2—C10—N1—C17	−179.06 (12)
C4—C2—C3—C6	0.4 (2)	C9—C10—N1—C17	−0.95 (13)
O1—C2—C4—C5	178.87 (13)	O2—C10—N1—C11	−17.53 (19)
C3—C2—C4—C5	0.7 (2)	C9—C10—N1—C11	160.58 (11)
C2—C4—C5—C7	−0.6 (2)	N2—C17—N1—C10	0.04 (14)
C2—C3—C6—C7	−1.6 (2)	N3—C17—N1—C10	179.73 (11)
C3—C6—C7—C5	1.7 (2)	N2—C17—N1—C11	−159.32 (12)
C3—C6—C7—C8	−178.28 (13)	N3—C17—N1—C11	20.37 (19)
C4—C5—C7—C6	−0.5 (2)	C12—C11—N1—C10	67.11 (16)
C4—C5—C7—C8	179.41 (13)	C16—C11—N1—C10	−109.60 (14)
C6—C7—C8—C9	169.16 (13)	C12—C11—N1—C17	−136.16 (14)
C5—C7—C8—C9	−10.8 (2)	C16—C11—N1—C17	47.13 (19)
C7—C8—C9—N2	−2.0 (2)	N3—C17—N2—C9	−178.73 (11)
C7—C8—C9—C10	178.77 (12)	N1—C17—N2—C9	0.95 (14)
C8—C9—C10—O2	−1.1 (2)	C8—C9—N2—C17	179.13 (13)
N2—C9—C10—O2	179.47 (13)	C10—C9—N2—C17	−1.53 (13)
C8—C9—C10—N1	−179.05 (11)	N2—C17—N3—C20	0.34 (19)
N2—C9—C10—N1	1.54 (13)	N1—C17—N3—C20	−179.31 (12)
C16—C11—C12—C13	−0.9 (2)	N2—C17—N3—C18	−139.27 (13)
N1—C11—C12—C13	−177.56 (14)	N1—C17—N3—C18	41.07 (17)
C11—C12—C13—C14	0.4 (3)	C21—C20—N3—C17	162.43 (13)
C12—C13—C14—C15	0.2 (3)	C21—C20—N3—C18	−54.39 (16)
C13—C14—C15—C16	−0.5 (3)	C19—C18—N3—C17	−162.09 (12)
C12—C11—C16—C15	0.6 (2)	C19—C18—N3—C20	56.42 (15)
N1—C11—C16—C15	177.29 (13)	C3—C2—O1—C1	−8.9 (2)
C14—C15—C16—C11	0.0 (3)	C4—C2—O1—C1	172.95 (17)
N3—C18—C19—O3	−58.51 (16)	C18—C19—O3—C21	58.76 (17)
N3—C20—C21—O3	55.06 (19)	C20—C21—O3—C19	−57.49 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O1^i	0.93	2.52	3.3843 (19)	156
C8—H8···O2^ii	0.93	2.41	3.3151 (16)	165
C18—H18B···N1	0.97	2.61	2.9596 (16)	102
C5—H5···N2	0.93	2.48	3.1072 (18)	125
C4—H4···O3^iii	0.93	2.47	3.3225 (17)	153

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y+1, −z+1; (iii) −x+2, −y, −z+1.