2-Diethyl­amino-3-phenyl­quinazolin-4(3H)-one

In the title compound, C₁₈H₁₉N₃O, the quinazoline system is approximately planar. The plane of the substituent phenyl ring forms a dihedral angle of 63.9 (2)° with respect to the mean plane of the quinazolinone ring system.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.052
• wR factor = 0.136
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?

   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

   2 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

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 (Sheldrick, 2001); software used to prepare material for publication: SHELXTL.

2-Diethylamino-3-phenylquinazolin-4(3H)-one

Crystal data

C18H19N3O	F(000) = 1248
Mr = 293.36	Dx = 1.275 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6145 reflections
a = 8.4259 (7) Å	θ = 2.5–27.0°
b = 10.9029 (9) Å	µ = 0.08 mm^−1
c = 33.263 (3) Å	T = 298 K
V = 3055.7 (4) Å^3	Block, white
Z = 8	0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer	3493 independent reflections
Radiation source: fine-focus sealed tube	2931 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.976, Tmax = 0.992	k = −11→14
17133 measured reflections	l = −32→43

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.136	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0701P)^2 + 0.7969P] where P = (Fo^2 + 2Fc^2)/3
3493 reflections	(Δ/σ)max = 0.001
201 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

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	−0.07854 (16)	0.33258 (12)	0.43151 (4)	0.0310 (3)
C2	−0.14396 (18)	0.32251 (14)	0.47019 (4)	0.0394 (3)
H2	−0.1071	0.3728	0.4907	0.047*
C3	−0.26190 (19)	0.23897 (15)	0.47792 (5)	0.0442 (4)
H3	−0.3042	0.2332	0.5037	0.053*
C4	−0.3190 (2)	0.16256 (14)	0.44756 (5)	0.0447 (4)
H4	−0.3967	0.1045	0.4532	0.054*
C5	−0.26032 (19)	0.17332 (14)	0.40938 (5)	0.0394 (3)
H5	−0.2998	0.1236	0.3890	0.047*
C6	−0.14113 (17)	0.25889 (12)	0.40089 (4)	0.0318 (3)
C7	−0.08523 (18)	0.27699 (12)	0.36012 (4)	0.0333 (3)
C8	0.10694 (16)	0.42092 (12)	0.38957 (4)	0.0304 (3)
C9	0.2853 (2)	0.57095 (15)	0.41804 (5)	0.0442 (4)
H9A	0.1909	0.5962	0.4325	0.053*
H9B	0.3357	0.6445	0.4077	0.053*
C10	0.3977 (2)	0.51009 (19)	0.44740 (5)	0.0596 (5)
H10A	0.3483	0.4383	0.4584	0.089*
H10B	0.4226	0.5663	0.4687	0.089*
H10C	0.4934	0.4871	0.4337	0.089*
C11	0.36586 (19)	0.46662 (16)	0.35509 (5)	0.0437 (4)
H11A	0.4521	0.5239	0.3595	0.052*
H11B	0.3270	0.4792	0.3279	0.052*
C12	0.4296 (2)	0.33789 (19)	0.35847 (6)	0.0623 (5)
H12A	0.4690	0.3246	0.3852	0.093*
H12B	0.5142	0.3268	0.3395	0.093*
H12C	0.3462	0.2804	0.3529	0.093*
C13	0.06835 (17)	0.40688 (13)	0.31531 (4)	0.0349 (3)
C14	0.0267 (2)	0.52554 (14)	0.30534 (5)	0.0435 (4)
H14	−0.0236	0.5758	0.3240	0.052*
C15	0.0610 (2)	0.56858 (17)	0.26701 (6)	0.0552 (5)
H15	0.0350	0.6487	0.2600	0.066*
C16	0.1330 (2)	0.4939 (2)	0.23948 (5)	0.0602 (5)
H16	0.1568	0.5238	0.2140	0.072*
C17	0.1704 (2)	0.37444 (18)	0.24928 (5)	0.0558 (5)
H17	0.2177	0.3237	0.2303	0.067*
C18	0.1376 (2)	0.32998 (15)	0.28735 (5)	0.0435 (4)
H18	0.1619	0.2493	0.2940	0.052*
N1	0.04961 (14)	0.40908 (11)	0.42562 (3)	0.0332 (3)
N2	0.03802 (14)	0.36402 (10)	0.35585 (3)	0.0324 (3)
N3	0.23635 (15)	0.49452 (11)	0.38375 (4)	0.0363 (3)
O1	−0.14044 (15)	0.22620 (10)	0.33059 (3)	0.0495 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0271 (7)	0.0323 (7)	0.0335 (7)	0.0023 (5)	−0.0013 (5)	0.0002 (5)
C2	0.0378 (8)	0.0452 (8)	0.0352 (8)	−0.0015 (6)	0.0015 (6)	−0.0015 (6)
C3	0.0393 (8)	0.0514 (9)	0.0417 (8)	−0.0013 (7)	0.0076 (7)	0.0067 (7)
C4	0.0373 (8)	0.0431 (8)	0.0538 (9)	−0.0088 (7)	0.0029 (7)	0.0079 (7)
C5	0.0370 (8)	0.0366 (8)	0.0446 (8)	−0.0053 (6)	−0.0061 (6)	0.0006 (6)
C6	0.0301 (7)	0.0301 (7)	0.0352 (7)	0.0019 (5)	−0.0041 (5)	0.0015 (5)
C7	0.0364 (8)	0.0294 (7)	0.0340 (7)	0.0003 (6)	−0.0052 (6)	0.0003 (5)
C8	0.0303 (7)	0.0289 (6)	0.0319 (7)	0.0014 (5)	−0.0022 (5)	−0.0012 (5)
C9	0.0433 (9)	0.0428 (8)	0.0466 (9)	−0.0155 (7)	0.0019 (7)	−0.0057 (7)
C10	0.0582 (11)	0.0727 (13)	0.0477 (10)	−0.0176 (9)	−0.0118 (8)	0.0001 (9)
C11	0.0341 (8)	0.0539 (9)	0.0430 (8)	−0.0078 (7)	0.0051 (6)	0.0033 (7)
C12	0.0492 (11)	0.0702 (13)	0.0676 (12)	0.0146 (9)	0.0080 (9)	0.0011 (10)
C13	0.0367 (8)	0.0388 (7)	0.0291 (7)	−0.0035 (6)	−0.0032 (6)	0.0017 (5)
C14	0.0433 (9)	0.0414 (8)	0.0459 (9)	0.0006 (7)	−0.0033 (7)	0.0050 (7)
C15	0.0562 (11)	0.0544 (10)	0.0552 (11)	−0.0050 (8)	−0.0110 (8)	0.0221 (8)
C16	0.0598 (12)	0.0828 (14)	0.0378 (9)	−0.0168 (10)	−0.0036 (8)	0.0196 (9)
C17	0.0582 (11)	0.0750 (12)	0.0340 (8)	−0.0068 (9)	0.0070 (7)	−0.0061 (8)
C18	0.0499 (9)	0.0440 (8)	0.0366 (8)	−0.0008 (7)	0.0003 (7)	−0.0022 (6)
N1	0.0323 (6)	0.0366 (6)	0.0307 (6)	−0.0040 (5)	0.0000 (5)	−0.0028 (5)
N2	0.0365 (6)	0.0326 (6)	0.0282 (6)	−0.0012 (5)	−0.0007 (5)	−0.0003 (4)
N3	0.0345 (6)	0.0392 (6)	0.0352 (6)	−0.0074 (5)	0.0024 (5)	−0.0011 (5)
O1	0.0615 (8)	0.0519 (7)	0.0352 (6)	−0.0175 (6)	−0.0075 (5)	−0.0055 (5)

Geometric parameters (Å, º)

C1—N1	1.3785 (18)	C10—H10B	0.960
C1—C6	1.4004 (19)	C10—H10C	0.960
C1—C2	1.404 (2)	C11—N3	1.4807 (19)
C2—C3	1.372 (2)	C11—C12	1.507 (3)
C2—H2	0.930	C11—H11A	0.970
C3—C4	1.395 (2)	C11—H11B	0.970
C3—H3	0.930	C12—H12A	0.960
C4—C5	1.368 (2)	C12—H12B	0.960
C4—H4	0.930	C12—H12C	0.960
C5—C6	1.400 (2)	C13—C14	1.381 (2)
C5—H5	0.930	C13—C18	1.381 (2)
C6—C7	1.4490 (19)	C13—N2	1.4499 (18)
C7—O1	1.2199 (17)	C14—C15	1.389 (2)
C7—N2	1.4139 (19)	C14—H14	0.930
C8—N1	1.2992 (18)	C15—C16	1.367 (3)
C8—N3	1.3677 (18)	C15—H15	0.930
C8—N2	1.4072 (17)	C16—C17	1.379 (3)
C9—N3	1.4716 (18)	C16—H16	0.930
C9—C10	1.513 (3)	C17—C18	1.384 (2)
C9—H9A	0.970	C17—H17	0.930
C9—H9B	0.970	C18—H18	0.930
C10—H10A	0.960
N1—C1—C6	122.60 (12)	N3—C11—H11A	108.8
N1—C1—C2	119.02 (12)	C12—C11—H11A	108.8
C6—C1—C2	118.29 (13)	N3—C11—H11B	108.8
C3—C2—C1	120.51 (14)	C12—C11—H11B	108.8
C3—C2—H2	119.7	H11A—C11—H11B	107.7
C1—C2—H2	119.7	C11—C12—H12A	109.5
C2—C3—C4	120.72 (15)	C11—C12—H12B	109.5
C2—C3—H3	119.6	H12A—C12—H12B	109.5
C4—C3—H3	119.6	C11—C12—H12C	109.5
C5—C4—C3	119.75 (14)	H12A—C12—H12C	109.5
C5—C4—H4	120.1	H12B—C12—H12C	109.5
C3—C4—H4	120.1	C14—C13—C18	120.96 (14)
C4—C5—C6	120.27 (14)	C14—C13—N2	118.72 (13)
C4—C5—H5	119.9	C18—C13—N2	120.33 (13)
C6—C5—H5	119.9	C13—C14—C15	118.94 (16)
C5—C6—C1	120.39 (13)	C13—C14—H14	120.5
C5—C6—C7	120.86 (13)	C15—C14—H14	120.5
C1—C6—C7	118.70 (13)	C16—C15—C14	120.39 (17)
O1—C7—N2	120.25 (13)	C16—C15—H15	119.8
O1—C7—C6	124.60 (14)	C14—C15—H15	119.8
N2—C7—C6	115.10 (12)	C15—C16—C17	120.36 (16)
N1—C8—N3	119.04 (12)	C15—C16—H16	119.8
N1—C8—N2	122.58 (13)	C17—C16—H16	119.8
N3—C8—N2	118.35 (12)	C16—C17—C18	120.11 (17)
N3—C9—C10	115.29 (14)	C16—C17—H17	119.9
N3—C9—H9A	108.5	C18—C17—H17	119.9
C10—C9—H9A	108.5	C13—C18—C17	119.19 (16)
N3—C9—H9B	108.5	C13—C18—H18	120.4
C10—C9—H9B	108.5	C17—C18—H18	120.4
H9A—C9—H9B	107.5	C8—N1—C1	118.85 (12)
C9—C10—H10A	109.5	C8—N2—C7	121.25 (11)
C9—C10—H10B	109.5	C8—N2—C13	121.77 (12)
H10A—C10—H10B	109.5	C7—N2—C13	116.06 (11)
C9—C10—H10C	109.5	C8—N3—C9	116.48 (12)
H10A—C10—H10C	109.5	C8—N3—C11	123.93 (12)
H10B—C10—H10C	109.5	C9—N3—C11	114.14 (12)
N3—C11—C12	113.95 (14)
N1—C1—C2—C3	−173.98 (14)	N2—C8—N1—C1	3.6 (2)
C6—C1—C2—C3	2.5 (2)	C6—C1—N1—C8	5.6 (2)
C1—C2—C3—C4	0.0 (2)	C2—C1—N1—C8	−178.02 (13)
C2—C3—C4—C5	−1.9 (2)	N1—C8—N2—C7	−8.8 (2)
C3—C4—C5—C6	1.3 (2)	N3—C8—N2—C7	173.33 (12)
C4—C5—C6—C1	1.3 (2)	N1—C8—N2—C13	159.84 (13)
C4—C5—C6—C7	−175.89 (14)	N3—C8—N2—C13	−18.06 (19)
N1—C1—C6—C5	173.21 (13)	O1—C7—N2—C8	−177.98 (13)
C2—C1—C6—C5	−3.2 (2)	C6—C7—N2—C8	4.37 (19)
N1—C1—C6—C7	−9.6 (2)	O1—C7—N2—C13	12.8 (2)
C2—C1—C6—C7	174.07 (13)	C6—C7—N2—C13	−164.85 (12)
C5—C6—C7—O1	3.9 (2)	C14—C13—N2—C8	−60.28 (19)
C1—C6—C7—O1	−173.31 (14)	C18—C13—N2—C8	119.73 (16)
C5—C6—C7—N2	−178.57 (13)	C14—C13—N2—C7	108.89 (15)
C1—C6—C7—N2	4.22 (19)	C18—C13—N2—C7	−71.10 (18)
C18—C13—C14—C15	−2.5 (2)	N1—C8—N3—C9	−9.66 (19)
N2—C13—C14—C15	177.55 (14)	N2—C8—N3—C9	168.31 (13)
C13—C14—C15—C16	0.9 (3)	N1—C8—N3—C11	142.69 (14)
C14—C15—C16—C17	0.8 (3)	N2—C8—N3—C11	−39.3 (2)
C15—C16—C17—C18	−1.1 (3)	C10—C9—N3—C8	87.15 (17)
C14—C13—C18—C17	2.2 (2)	C10—C9—N3—C11	−67.90 (18)
N2—C13—C18—C17	−177.77 (15)	C12—C11—N3—C8	−48.8 (2)
C16—C17—C18—C13	−0.5 (3)	C12—C11—N3—C9	104.13 (17)
N3—C8—N1—C1	−178.51 (12)