3-[4-(Dimethyl­amino)benzyl­ideneamino]-2-methyl­quinazolin-4(3H)-one

Kumaradhas, P.; Sankara Lakshmi, G.; Sridhar, B.; Paneer Selvam, P.; Saravanan, G.

doi:10.1107/S1600536807047393

3-[4-(Dimethylamino)benzylideneamino]-2-methylquinazolin-4(3H)-one

P. Kumaradhas, G. Sankara Lakshmi, B. Sridhar, P. Paneer Selvam and G. Saravanan

In the title compound, C₁₈H₁₈N₄O, the dihedral angle between the quinazoline and benzylidene groups is 54.0 (4)°. In the crystal structure, the molecules associate into centrosymmetric dimers via C—H

O interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047393/hb2537sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047393/hb2537Isup2.hkl Contains datablock I

CCDC reference: 667337

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R factor = 0.049
wR factor = 0.149
Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        200 Deg.
PLAT391_ALERT_3_C Deviating Methyl C17     H-C-H Bond Angle ......     100.00 Deg.

   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

   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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Quinazolin related compounds exhibit multiple medicinal activities, such as analgesic (Alagarsamy et al., 2004), anti-inflammatory (Alagarsamy et al., 2003), and anticonvulsant (El-Meligie et al., 2001) properties. As part of our studies of these systems, we now present the synthesis and structure of the title compound, (I), (Fig. 1).

In the quinazolin ring, the single bond C—N distances [C8—N2 = 1.385 (2) Å; C7—N2 = 1.398 (2) Å and C3—N1 = 1.387 (2) Å] are almost equal and longer than C14—N4 [1.364 (2) Å]. The non-ring C—N bond distances such as C17—N4 and C18—N4 are significantly, longer than the above C—N distances. These differences are attributed to the different attached groups. As expected, the bridging bond C10—C11 [1.447 (2) Å] is much longer than the C—C distances of the rings in the molecule. The torsion angles N3—N2—C8—C9 and O1—C7—N2—N3 are -7.9 (2)° and 8.3 (2)° respectively. This small angle of bond twist indicate that the bonded atoms are cis oriented. In the molecule, the quinazolin ring and the benzylidene group are twisted with each other and the corresponding torsion angle is -178.2 (2)° confirms that the bonds are trans oriented. This wide-angle twist indicates that the the groups are significantly rotated and the dihedral angle between the planes is 54.0 (4)°. A small value of the dihedral angle [2.10 (4)°] between the aromatic and quinazolin rings show they are almost coplanar. The quinazolin ring is statistically planar with a maximum deviation of 0.02 (1) Å [C8].

The molecular packing is stabilized by C—H···O hydrogen bonding interactions which result in centrosymmetric dimers (Table 1, Fig. 2).

Related literature top

For related literature, see: Alagarsamy et al. (2003, 2004); El-Meligie et al. (2001).

Experimental top

A mixture of 2–methyl benzo(1,3) oxazin–4–one (0.01 mole; 1.61 g) and hydrazine hydrate (0.03 mole; 1.5 g) in ethanol was refluxed for two hours, then p-dimethyl amino benzaldehyde (2.24 g) was added. Then the solution was poured into ice cold water. The separated solid was filtered and recrystallized from ethanol and dried in an oven. Yield 73.1%; melting point 412–414 K. Yellow needles of (I) were recrystallized from ethyl acetate solution.

Structure description top

The molecular packing is stabilized by C—H···O hydrogen bonding interactions which result in centrosymmetric dimers (Table 1, Fig. 2).

For related literature, see: Alagarsamy et al. (2003, 2004); El-Meligie et al. (2001).

Computing details top

Data collection: APEX2 not SMART (Bruker, ????); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. View of the molecular structure of (I). The displacement ellipsoids are drawn at 50% probability level and H atoms are drawn as spheres of arbitrary radius.
	Fig. 2. A centrosymmetric dimer of (I), linked by C—H···O interactions. Atom marked with an asterisk (*) are at the symmetry position (-x, -y, 1 - z).

3-[4-(Dimethylamino)benzylideneamino]-2-methylquinazolin-4(3H)-one top

Crystal data top

C₁₈H₁₈N₄O	Z = 2
M_r = 306.36	F(000) = 324
Triclinic, P1	D_x = 1.301 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5175 (10) Å	Cell parameters from 50 reflections
b = 9.3631 (13) Å	θ = 1.7–28.0°
c = 12.7886 (17) Å	µ = 0.08 mm⁻¹
α = 98.198 (2)°	T = 296 K
β = 103.259 (2)°	Block, yellow
γ = 112.517 (2)°	0.21 × 0.18 × 0.10 mm
V = 782.33 (18) Å³

Data collection top

Bruker APEXII CCD diffractometer	R_int = 0.021
ω scans	θ_max = 28.0°, θ_min = 1.7°
9011 measured reflections	h = −9→9
3582 independent reflections	k = −12→12
2863 reflections with I > 2σ(I)	l = −16→16

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	All H-atom parameters refined
R[F² > 2σ(F²)] = 0.049	w = 1/[σ²(F_o²) + (0.0824P)² + 0.0881P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.150	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 0.16 e Å⁻³
3582 reflections	Δρ_min = −0.18 e Å⁻³
280 parameters

Crystal data top

C₁₈H₁₈N₄O	γ = 112.517 (2)°
M_r = 306.36	V = 782.33 (18) Å³
Triclinic, P1	Z = 2
a = 7.5175 (10) Å	Mo Kα radiation
b = 9.3631 (13) Å	µ = 0.08 mm⁻¹
c = 12.7886 (17) Å	T = 296 K
α = 98.198 (2)°	0.21 × 0.18 × 0.10 mm
β = 103.259 (2)°

Data collection top

Bruker APEXII CCD diffractometer	2863 reflections with I > 2σ(I)
9011 measured reflections	R_int = 0.021
3582 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.150	All H-atom parameters refined
S = 1.03	Δρ_max = 0.16 e Å⁻³
3582 reflections	Δρ_min = −0.18 e Å⁻³
280 parameters

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	−0.0239 (3)	0.7144 (2)	0.16094 (15)	0.0761 (5)
C2	0.1029 (2)	0.63717 (16)	0.16193 (11)	0.0590 (4)
C3	0.2288 (3)	0.66170 (16)	0.09561 (11)	0.0628 (4)
C4	0.2239 (4)	0.7645 (2)	0.02596 (14)	0.0830 (5)
C5	0.0992 (4)	0.8384 (2)	0.02555 (17)	0.0969 (7)
C6	−0.0240 (4)	0.8146 (2)	0.09299 (16)	0.0937 (7)
C7	0.0971 (2)	0.52499 (16)	0.23043 (11)	0.0574 (3)
C8	0.3481 (2)	0.48483 (17)	0.15228 (11)	0.0584 (3)
C9	0.4731 (3)	0.3951 (3)	0.14777 (16)	0.0759 (5)
C10	0.25148 (19)	0.35813 (15)	0.37531 (11)	0.0494 (3)
C11	0.25379 (18)	0.23922 (15)	0.43582 (10)	0.0468 (3)
C12	0.2940 (2)	0.27515 (16)	0.55046 (11)	0.0513 (3)
C13	0.3045 (2)	0.16600 (17)	0.61039 (11)	0.0536 (3)
C14	0.27102 (18)	0.01191 (15)	0.55708 (10)	0.0482 (3)
C15	0.2322 (2)	−0.02347 (16)	0.44130 (11)	0.0539 (3)
C16	0.2239 (2)	0.08687 (16)	0.38322 (11)	0.0532 (3)
C17	0.3175 (4)	−0.0651 (3)	0.73240 (15)	0.0841 (6)
C18	0.2354 (3)	−0.25892 (19)	0.55635 (16)	0.0678 (4)
N1	0.3542 (2)	0.58551 (16)	0.09249 (10)	0.0669 (4)
N2	0.22998 (18)	0.45569 (13)	0.22242 (9)	0.0528 (3)
N3	0.22249 (19)	0.32720 (13)	0.27105 (9)	0.0566 (3)
N4	0.27461 (19)	−0.10011 (14)	0.61397 (10)	0.0593 (3)
O1	−0.01214 (18)	0.49096 (15)	0.28877 (10)	0.0773 (4)
H1	−0.117 (3)	0.691 (3)	0.2099 (18)	0.104 (7)*
H4	0.315 (3)	0.783 (2)	−0.0153 (17)	0.085 (6)*
H5	0.097 (4)	0.905 (3)	−0.023 (2)	0.119 (7)*
H6	−0.120 (4)	0.861 (3)	0.0914 (19)	0.110 (7)*
H9A	0.385 (4)	0.279 (3)	0.1317 (19)	0.114 (7)*
H9B	0.575 (3)	0.424 (2)	0.2179 (19)	0.097 (6)*
H9C	0.532 (3)	0.415 (2)	0.0904 (17)	0.089 (6)*
H10	0.279 (2)	0.4627 (18)	0.4204 (12)	0.057 (4)*
H12	0.313 (2)	0.378 (2)	0.5871 (13)	0.063 (4)*
H13	0.333 (2)	0.1965 (19)	0.6874 (15)	0.072 (5)*
H15	0.211 (2)	−0.125 (2)	0.4051 (13)	0.068 (4)*
H16	0.196 (2)	0.0572 (19)	0.3046 (14)	0.070 (4)*
H17A	0.243 (4)	−0.015 (3)	0.757 (2)	0.135 (10)*
H17B	0.455 (4)	0.021 (3)	0.766 (2)	0.126 (8)*
H17C	0.314 (4)	−0.156 (3)	0.757 (2)	0.118 (7)*
H18A	0.097 (3)	−0.314 (2)	0.4942 (16)	0.088 (5)*
H18B	0.236 (4)	−0.319 (3)	0.6088 (19)	0.116 (7)*
H18C	0.336 (3)	−0.255 (2)	0.5189 (16)	0.093 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0992 (12)	0.0659 (9)	0.0662 (9)	0.0470 (9)	0.0123 (9)	0.0144 (7)
C2	0.0747 (9)	0.0475 (7)	0.0453 (7)	0.0256 (6)	0.0048 (6)	0.0090 (5)
C3	0.0849 (10)	0.0481 (7)	0.0441 (7)	0.0242 (7)	0.0071 (6)	0.0122 (5)
C4	0.1266 (16)	0.0663 (10)	0.0574 (9)	0.0415 (11)	0.0240 (10)	0.0282 (8)
C5	0.158 (2)	0.0683 (11)	0.0683 (11)	0.0602 (13)	0.0138 (12)	0.0297 (9)
C6	0.1408 (19)	0.0795 (12)	0.0722 (11)	0.0703 (13)	0.0122 (12)	0.0210 (9)
C7	0.0660 (8)	0.0531 (7)	0.0513 (7)	0.0270 (6)	0.0121 (6)	0.0145 (6)
C8	0.0695 (8)	0.0597 (8)	0.0453 (7)	0.0268 (7)	0.0162 (6)	0.0168 (6)
C9	0.0916 (12)	0.0981 (14)	0.0661 (10)	0.0562 (11)	0.0376 (10)	0.0384 (10)
C10	0.0482 (7)	0.0472 (6)	0.0506 (7)	0.0196 (5)	0.0122 (5)	0.0143 (5)
C11	0.0436 (6)	0.0477 (6)	0.0490 (6)	0.0191 (5)	0.0128 (5)	0.0156 (5)
C12	0.0546 (7)	0.0479 (7)	0.0504 (7)	0.0222 (6)	0.0152 (5)	0.0111 (5)
C13	0.0584 (7)	0.0575 (7)	0.0439 (7)	0.0243 (6)	0.0145 (5)	0.0143 (5)
C14	0.0422 (6)	0.0523 (7)	0.0537 (7)	0.0211 (5)	0.0160 (5)	0.0202 (5)
C15	0.0621 (8)	0.0482 (7)	0.0547 (7)	0.0262 (6)	0.0193 (6)	0.0139 (6)
C16	0.0614 (8)	0.0533 (7)	0.0451 (7)	0.0248 (6)	0.0158 (6)	0.0140 (5)
C17	0.1134 (16)	0.0731 (11)	0.0595 (9)	0.0356 (12)	0.0155 (10)	0.0306 (8)
C18	0.0755 (10)	0.0576 (8)	0.0822 (11)	0.0337 (8)	0.0294 (9)	0.0308 (8)
N1	0.0867 (9)	0.0676 (7)	0.0515 (7)	0.0335 (7)	0.0240 (6)	0.0259 (6)
N2	0.0647 (7)	0.0482 (6)	0.0464 (6)	0.0245 (5)	0.0152 (5)	0.0176 (4)
N3	0.0719 (7)	0.0502 (6)	0.0534 (6)	0.0290 (5)	0.0197 (5)	0.0218 (5)
N4	0.0667 (7)	0.0593 (7)	0.0600 (7)	0.0306 (6)	0.0209 (5)	0.0269 (5)
O1	0.0864 (8)	0.0928 (8)	0.0825 (8)	0.0533 (7)	0.0408 (6)	0.0441 (6)

Geometric parameters (Å, º) top

C1—C6	1.367 (3)	C10—H10	0.982 (15)
C1—C2	1.399 (2)	C11—C12	1.3900 (18)
C1—H1	1.03 (2)	C11—C16	1.3963 (18)
C2—C3	1.387 (2)	C12—C13	1.3768 (18)
C2—C7	1.4552 (19)	C12—H12	0.950 (16)
C3—N1	1.387 (2)	C13—C14	1.4044 (19)
C3—C4	1.406 (2)	C13—H13	0.934 (17)
C4—C5	1.362 (3)	C14—N4	1.3641 (16)
C4—H4	0.939 (19)	C14—C15	1.4054 (19)
C5—C6	1.384 (3)	C15—C16	1.3673 (18)
C5—H5	0.95 (2)	C15—H15	0.931 (16)
C6—H6	0.97 (2)	C16—H16	0.955 (17)
C7—O1	1.2171 (18)	C17—N4	1.435 (2)
C7—N2	1.3976 (19)	C17—H17A	0.94 (3)
C8—N1	1.2899 (17)	C17—H17B	0.98 (3)
C8—N2	1.3848 (18)	C17—H17C	0.94 (3)
C8—C9	1.486 (2)	C18—N4	1.447 (2)
C9—H9A	1.00 (2)	C18—H18A	1.03 (2)
C9—H9B	0.96 (2)	C18—H18B	0.94 (2)
C9—H9C	0.95 (2)	C18—H18C	0.98 (2)
C10—N3	1.2718 (17)	N2—N3	1.4194 (14)
C10—C11	1.4467 (17)

C6—C1—C2	119.2 (2)	C13—C12—C11	121.83 (12)
C6—C1—H1	122.1 (12)	C13—C12—H12	120.1 (9)
C2—C1—H1	118.6 (12)	C11—C12—H12	118.0 (9)
C3—C2—C1	120.97 (14)	C12—C13—C14	120.87 (12)
C3—C2—C7	119.54 (13)	C12—C13—H13	118.4 (10)
C1—C2—C7	119.46 (15)	C14—C13—H13	120.7 (10)
N1—C3—C2	122.88 (12)	N4—C14—C13	122.11 (12)
N1—C3—C4	118.69 (16)	N4—C14—C15	120.78 (12)
C2—C3—C4	118.40 (16)	C13—C14—C15	117.12 (11)
C5—C4—C3	120.0 (2)	C16—C15—C14	121.21 (12)
C5—C4—H4	123.4 (12)	C16—C15—H15	120.8 (10)
C3—C4—H4	116.5 (12)	C14—C15—H15	118.0 (10)
C4—C5—C6	121.16 (17)	C15—C16—C11	121.76 (12)
C4—C5—H5	118.5 (15)	C15—C16—H16	118.2 (10)
C6—C5—H5	120.4 (15)	C11—C16—H16	120.1 (10)
C1—C6—C5	120.2 (2)	N4—C17—H17A	112.6 (17)
C1—C6—H6	116.6 (14)	N4—C17—H17B	107.8 (15)
C5—C6—H6	123.0 (14)	H17A—C17—H17B	100 (2)
O1—C7—N2	121.87 (12)	N4—C17—H17C	109.6 (15)
O1—C7—C2	124.86 (14)	H17A—C17—H17C	117 (2)
N2—C7—C2	113.27 (13)	H17B—C17—H17C	108 (2)
N1—C8—N2	123.02 (13)	N4—C18—H18A	111.7 (10)
N1—C8—C9	119.66 (14)	N4—C18—H18B	107.7 (14)
N2—C8—C9	117.33 (13)	H18A—C18—H18B	109.7 (18)
C8—C9—H9A	109.1 (14)	N4—C18—H18C	111.0 (12)
C8—C9—H9B	111.3 (12)	H18A—C18—H18C	105.4 (16)
H9A—C9—H9B	107.1 (18)	H18B—C18—H18C	111.3 (18)
C8—C9—H9C	108.8 (12)	C8—N1—C3	117.79 (13)
H9A—C9—H9C	109.7 (18)	C8—N2—C7	123.41 (11)
H9B—C9—H9C	110.8 (18)	C8—N2—N3	115.22 (11)
N3—C10—C11	120.72 (12)	C7—N2—N3	120.37 (11)
N3—C10—H10	123.6 (8)	C10—N3—N2	115.05 (11)
C11—C10—H10	115.6 (8)	C14—N4—C17	121.49 (13)
C12—C11—C16	117.20 (11)	C14—N4—C18	120.79 (13)
C12—C11—C10	120.75 (12)	C17—N4—C18	117.72 (14)
C16—C11—C10	122.01 (11)

C6—C1—C2—C3	0.4 (2)	C13—C14—C15—C16	−1.1 (2)
C6—C1—C2—C7	−177.34 (15)	C14—C15—C16—C11	0.1 (2)
C1—C2—C3—N1	−178.80 (13)	C12—C11—C16—C15	0.5 (2)
C7—C2—C3—N1	−1.1 (2)	C10—C11—C16—C15	178.05 (12)
C1—C2—C3—C4	−0.9 (2)	N2—C8—N1—C3	−3.0 (2)
C7—C2—C3—C4	176.80 (13)	C9—C8—N1—C3	177.34 (15)
N1—C3—C4—C5	178.65 (16)	C2—C3—N1—C8	1.7 (2)
C2—C3—C4—C5	0.7 (3)	C4—C3—N1—C8	−176.17 (14)
C3—C4—C5—C6	0.1 (3)	N1—C8—N2—C7	3.9 (2)
C2—C1—C6—C5	0.4 (3)	C9—C8—N2—C7	−176.45 (15)
C4—C5—C6—C1	−0.7 (3)	N1—C8—N2—N3	172.45 (12)
C3—C2—C7—O1	−177.59 (14)	C9—C8—N2—N3	−7.92 (19)
C1—C2—C7—O1	0.1 (2)	O1—C7—N2—C8	176.29 (13)
C3—C2—C7—N2	1.63 (18)	C2—C7—N2—C8	−2.96 (19)
C1—C2—C7—N2	179.36 (13)	O1—C7—N2—N3	8.3 (2)
N3—C10—C11—C12	177.24 (12)	C2—C7—N2—N3	−170.92 (11)
N3—C10—C11—C16	−0.3 (2)	C11—C10—N3—N2	−178.16 (10)
C16—C11—C12—C13	0.07 (19)	C8—N2—N3—C10	132.15 (13)
C10—C11—C12—C13	−177.54 (11)	C7—N2—N3—C10	−58.94 (16)
C11—C12—C13—C14	−1.2 (2)	C13—C14—N4—C17	−1.4 (2)
C12—C13—C14—N4	−178.04 (11)	C15—C14—N4—C17	178.90 (16)
C12—C13—C14—C15	1.67 (19)	C13—C14—N4—C18	178.72 (13)
N4—C14—C15—C16	178.58 (12)	C15—C14—N4—C18	−1.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18B···O1ⁱ	0.94 (2)	2.58 (3)	3.379 (2)	143.0 (19)

Symmetry code: (i) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈N₄O
M_r	306.36
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.5175 (10), 9.3631 (13), 12.7886 (17)
α, β, γ (°)	98.198 (2), 103.259 (2), 112.517 (2)
V (Å³)	782.33 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.21 × 0.18 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9011, 3582, 2863
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.660

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.150, 1.03
No. of reflections	3582
No. of parameters	280
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.18

Computer programs: APEX2 not SMART (Bruker, ????), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003), WinGX (Farrugia, 1999).