3-(2-Amino-ethyl)-2-anilinoquinazolin-4(3H)-one methanol hemisolvate.

The title methanol hemisolvated quinazolin-(3H)-one, C(16)H(16)N(4)O·0.5CH(3)OH, has an anilino substituent in the 2-position and an amino-ethyl substituent in the 3-position of the planar fused-ring system (r.m.s. deviation = 0.019 Å). The anilino N atom donates an intramolecular hydrogen bond to the amino-ethyl N atom. The mol-ecule and the solvent methanol mol-ecule are linked by N-H⋯N, N-H⋯O and O-H⋯O hydrogen bonds. The methanol mol-ecule is disordered over two equally occupied positions about a twofold rotation axis.

Related literature

For the synthesis of this class of compounds, see: Yang et al. (2008 ▶). For the crystal structure of a chlorine-substituted derivative, see: Yang et al. (2009 ▶).

Experimental

Crystal data

C16H16N4O·0.5CH4O

M = 296.35

Monoclinic,

a = 19.5972 (11) Å

b = 12.2035 (7) Å

c = 12.8681 (8) Å

β = 103.301 (1)°

V = 2994.9 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.30 × 0.20 × 0.10 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: none

14007 measured reflections

3399 independent reflections

2377 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.186

S = 1.09

3399 reflections

210 parameters

13 restraints

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045516/bt5121sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045516/bt5121Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H16N4O·0.5CH4O	F(000) = 1256
Mr = 296.35	Dx = 1.314 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3816 reflections
a = 19.5972 (11) Å	θ = 2.4–25.9°
b = 12.2035 (7) Å	µ = 0.09 mm−1
c = 12.8681 (8) Å	T = 295 K
β = 103.301 (1)°	Block, colorless
V = 2994.9 (3) Å3	0.30 × 0.20 × 0.10 mm
Z = 8

Bruker APEXII diffractometer	2377 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.073
graphite	θmax = 27.5°, θmin = 2.0°
ω scans	h = −17→25
14007 measured reflections	k = −15→14
3399 independent reflections	l = −16→16

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.186	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.1044P)2 + 0.1504P] where P = (Fo2 + 2Fc2)/3
3399 reflections	(Δ/σ)max = 0.001
210 parameters	Δρmax = 0.55 e Å−3
13 restraints	Δρmin = −0.29 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.68958 (7)	0.41303 (12)	0.81309 (11)	0.0573 (4)
N1	0.73674 (8)	0.41620 (12)	0.66714 (11)	0.0424 (4)
N2	0.84958 (8)	0.34284 (13)	0.67038 (11)	0.0458 (4)
N3	0.77752 (9)	0.40366 (13)	0.51241 (12)	0.0498 (4)
H31	0.7345	0.4239	0.4817	0.060*
N4	0.63136 (9)	0.37965 (16)	0.44490 (14)	0.0632 (5)
H41	0.6131	0.4263	0.3939	0.076*
H42	0.6131	0.3143	0.4284	0.076*
C1	0.80430 (10)	0.34133 (14)	0.83148 (13)	0.0414 (4)
C2	0.81360 (11)	0.31401 (16)	0.93932 (14)	0.0503 (5)
H2	0.7782	0.3290	0.9746	0.060*
C3	0.87449 (12)	0.26533 (18)	0.99341 (15)	0.0576 (6)
H3	0.8804	0.2465	1.0650	0.069*
C4	0.92707 (11)	0.24457 (19)	0.94030 (15)	0.0589 (6)
H4	0.9684	0.2115	0.9767	0.071*
C5	0.91908 (11)	0.27202 (19)	0.83510 (16)	0.0573 (6)
H5	0.9552	0.2579	0.8011	0.069*
C6	0.85720 (10)	0.32115 (15)	0.77791 (13)	0.0427 (5)
C7	0.73916 (10)	0.39143 (15)	0.77321 (14)	0.0437 (5)
C8	0.79099 (10)	0.38642 (15)	0.61962 (14)	0.0414 (4)
C9	0.82431 (10)	0.39287 (14)	0.44502 (14)	0.0426 (5)
C10	0.79487 (10)	0.36669 (15)	0.33875 (14)	0.0462 (5)
H10	0.7472	0.3515	0.3175	0.055*
C11	0.83579 (12)	0.36311 (17)	0.26507 (15)	0.0530 (5)
H11	0.8154	0.3462	0.1942	0.064*
C12	0.90627 (13)	0.38417 (19)	0.29508 (18)	0.0614 (6)
H12	0.9338	0.3820	0.2451	0.074*
C13	0.93592 (12)	0.40868 (19)	0.40098 (18)	0.0616 (6)
H13	0.9838	0.4225	0.4220	0.074*
C14	0.89551 (11)	0.41293 (17)	0.47595 (16)	0.0534 (5)
H14	0.9161	0.4292	0.5468	0.064*
C15	0.67613 (10)	0.48235 (17)	0.61029 (15)	0.0516 (5)
H15A	0.6922	0.5335	0.5634	0.062*
H15B	0.6587	0.5248	0.6624	0.062*
C16	0.61626 (11)	0.41579 (18)	0.54480 (17)	0.0586 (6)
H16A	0.6080	0.3524	0.5857	0.070*
H16B	0.5739	0.4599	0.5298	0.070*
O2	0.5495 (3)	0.4637 (6)	0.7850 (7)	0.176 (3)	0.50
H2O	0.5856	0.4244	0.8006	0.211*	0.50
C17	0.4883 (4)	0.3949 (6)	0.7344 (11)	0.101 (3)	0.50
H17A	0.4553	0.3937	0.7792	0.152*	0.50
H17B	0.5037	0.3216	0.7254	0.152*	0.50
H17C	0.4662	0.4250	0.6660	0.152*	0.50

	U11	U22	U33	U12	U13	U23
O1	0.0468 (8)	0.0701 (10)	0.0607 (8)	0.0019 (7)	0.0243 (7)	−0.0043 (6)
N1	0.0402 (9)	0.0437 (9)	0.0438 (8)	0.0002 (7)	0.0110 (7)	−0.0028 (6)
N2	0.0417 (9)	0.0570 (10)	0.0402 (8)	0.0011 (7)	0.0130 (7)	−0.0002 (6)
N3	0.0430 (9)	0.0665 (11)	0.0405 (8)	0.0019 (8)	0.0107 (7)	0.0053 (7)
N4	0.0614 (12)	0.0661 (12)	0.0558 (10)	0.0053 (9)	0.0006 (9)	−0.0015 (8)
C1	0.0435 (10)	0.0412 (10)	0.0411 (9)	−0.0070 (8)	0.0128 (8)	−0.0050 (7)
C2	0.0578 (13)	0.0540 (12)	0.0437 (10)	−0.0063 (10)	0.0214 (9)	−0.0038 (8)
C3	0.0697 (14)	0.0649 (13)	0.0384 (9)	−0.0019 (11)	0.0128 (10)	0.0028 (9)
C4	0.0490 (12)	0.0744 (15)	0.0494 (11)	0.0035 (11)	0.0035 (10)	0.0062 (9)
C5	0.0446 (12)	0.0782 (15)	0.0510 (11)	0.0058 (10)	0.0152 (9)	0.0035 (10)
C6	0.0424 (10)	0.0490 (11)	0.0378 (9)	−0.0038 (8)	0.0112 (8)	−0.0014 (7)
C7	0.0443 (11)	0.0438 (10)	0.0459 (10)	−0.0063 (8)	0.0164 (8)	−0.0070 (7)
C8	0.0413 (10)	0.0424 (10)	0.0415 (9)	−0.0040 (8)	0.0112 (8)	−0.0027 (7)
C9	0.0445 (11)	0.0432 (10)	0.0411 (9)	−0.0007 (8)	0.0122 (8)	0.0067 (7)
C10	0.0482 (11)	0.0448 (11)	0.0440 (9)	−0.0001 (8)	0.0072 (8)	0.0011 (7)
C11	0.0636 (14)	0.0570 (12)	0.0404 (9)	0.0007 (10)	0.0159 (9)	−0.0006 (8)
C12	0.0654 (15)	0.0711 (15)	0.0554 (12)	0.0043 (11)	0.0293 (11)	0.0041 (10)
C13	0.0466 (12)	0.0792 (16)	0.0620 (13)	−0.0042 (10)	0.0187 (10)	0.0085 (10)
C14	0.0490 (12)	0.0683 (14)	0.0423 (10)	−0.0097 (10)	0.0091 (9)	0.0032 (9)
C15	0.0507 (12)	0.0492 (12)	0.0548 (11)	0.0090 (9)	0.0119 (9)	−0.0007 (8)
C16	0.0445 (12)	0.0671 (14)	0.0618 (13)	0.0074 (10)	0.0071 (10)	0.0025 (10)
O2	0.109 (4)	0.189 (6)	0.231 (6)	−0.017 (4)	0.043 (4)	−0.115 (5)
C17	0.044 (6)	0.143 (5)	0.117 (8)	0.021 (4)	0.017 (5)	0.021 (5)

O1—C7	1.227 (2)	C5—H5	0.9300
N1—C7	1.388 (2)	C9—C14	1.382 (3)
N1—C8	1.391 (2)	C9—C10	1.394 (2)
N1—C15	1.482 (2)	C10—C11	1.376 (3)
N2—C8	1.297 (2)	C10—H10	0.9300
N2—C6	1.383 (2)	C11—C12	1.370 (3)
N3—C8	1.360 (2)	C11—H11	0.9300
N3—C9	1.406 (2)	C12—C13	1.386 (3)
N3—H31	0.8800	C12—H12	0.9300
N4—C16	1.453 (3)	C13—C14	1.383 (3)
N4—H41	0.8800	C13—H13	0.9300
N4—H42	0.8800	C14—H14	0.9300
C1—C6	1.393 (3)	C15—C16	1.514 (3)
C1—C2	1.398 (2)	C15—H15A	0.9700
C1—C7	1.458 (3)	C15—H15B	0.9700
C2—C3	1.371 (3)	C16—H16A	0.9700
C2—H2	0.9300	C16—H16B	0.9700
C3—C4	1.385 (3)	O2—C17	1.486 (2)
C3—H3	0.9300	O2—H2O	0.8400
C4—C5	1.368 (3)	C17—H17A	0.9600
C4—H4	0.9300	C17—H17B	0.9600
C5—C6	1.400 (3)	C17—H17C	0.9600
C7—N1—C8	121.23 (15)	N2—C8—N1	124.28 (16)
C7—N1—C15	116.50 (15)	N3—C8—N1	114.57 (16)
C8—N1—C15	122.13 (15)	C14—C9—C10	119.07 (18)
C8—N2—C6	117.49 (16)	C14—C9—N3	124.37 (17)
C8—N3—C9	127.54 (17)	C10—C9—N3	116.44 (17)
C8—N3—H31	116.2	C11—C10—C9	120.53 (19)
C9—N3—H31	116.2	C11—C10—H10	119.7
C16—N4—H41	109.5	C9—C10—H10	119.7
C16—N4—H42	109.5	C12—C11—C10	120.61 (19)
H41—N4—H42	109.5	C12—C11—H11	119.7
C6—C1—C2	120.49 (17)	C10—C11—H11	119.7
C6—C1—C7	118.89 (16)	C11—C12—C13	119.0 (2)
C2—C1—C7	120.62 (18)	C11—C12—H12	120.5
C3—C2—C1	120.45 (19)	C13—C12—H12	120.5
C3—C2—H2	119.8	C14—C13—C12	121.1 (2)
C1—C2—H2	119.8	C14—C13—H13	119.5
C2—C3—C4	119.24 (17)	C12—C13—H13	119.5
C2—C3—H3	120.4	C9—C14—C13	119.66 (19)
C4—C3—H3	120.4	C9—C14—H14	120.2
C5—C4—C3	120.99 (19)	C13—C14—H14	120.2
C5—C4—H4	119.5	N1—C15—C16	114.39 (17)
C3—C4—H4	119.5	N1—C15—H15A	108.7
C4—C5—C6	120.9 (2)	C16—C15—H15A	108.7
C4—C5—H5	119.6	N1—C15—H15B	108.7
C6—C5—H5	119.6	C16—C15—H15B	108.7
N2—C6—C1	122.70 (17)	H15A—C15—H15B	107.6
N2—C6—C5	119.27 (17)	N4—C16—C15	111.46 (19)
C1—C6—C5	117.96 (16)	N4—C16—H16A	109.3
O1—C7—N1	120.87 (17)	C15—C16—H16A	109.3
O1—C7—C1	123.97 (17)	N4—C16—H16B	109.3
N1—C7—C1	115.15 (16)	C15—C16—H16B	109.3
N2—C8—N3	121.13 (18)	H16A—C16—H16B	108.0
C6—C1—C2—C3	−1.1 (3)	C6—N2—C8—N3	−175.64 (16)
C7—C1—C2—C3	178.97 (17)	C6—N2—C8—N1	2.5 (3)
C1—C2—C3—C4	0.7 (3)	C9—N3—C8—N2	−9.1 (3)
C2—C3—C4—C5	0.1 (3)	C9—N3—C8—N1	172.63 (16)
C3—C4—C5—C6	−0.5 (4)	C7—N1—C8—N2	−6.1 (3)
C8—N2—C6—C1	1.8 (3)	C15—N1—C8—N2	169.49 (18)
C8—N2—C6—C5	178.68 (18)	C7—N1—C8—N3	172.12 (15)
C2—C1—C6—N2	177.50 (16)	C15—N1—C8—N3	−12.3 (2)
C7—C1—C6—N2	−2.5 (3)	C8—N3—C9—C14	−31.8 (3)
C2—C1—C6—C5	0.6 (3)	C8—N3—C9—C10	152.29 (18)
C7—C1—C6—C5	−179.41 (17)	C14—C9—C10—C11	−1.4 (3)
C4—C5—C6—N2	−176.84 (19)	N3—C9—C10—C11	174.75 (17)
C4—C5—C6—C1	0.2 (3)	C9—C10—C11—C12	0.6 (3)
C8—N1—C7—O1	−176.29 (16)	C10—C11—C12—C13	0.3 (3)
C15—N1—C7—O1	7.9 (3)	C11—C12—C13—C14	−0.5 (3)
C8—N1—C7—C1	4.9 (2)	C10—C9—C14—C13	1.2 (3)
C15—N1—C7—C1	−170.91 (15)	N3—C9—C14—C13	−174.6 (2)
C6—C1—C7—O1	−179.64 (17)	C12—C13—C14—C9	−0.3 (3)
C2—C1—C7—O1	0.3 (3)	C7—N1—C15—C16	−96.6 (2)
C6—C1—C7—N1	−0.9 (2)	C8—N1—C15—C16	87.6 (2)
C2—C1—C7—N1	179.07 (16)	N1—C15—C16—N4	−77.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H31···N4	0.88	2.04	2.811 (3)	146
N4—H41···O2i	0.88	2.13	2.990 (6)	168
O2—H2O···O1	0.84	2.01	2.755 (6)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H31⋯N4	0.88	2.04	2.811 (3)	146
N4—H41⋯O2i	0.88	2.13	2.990 (6)	168
O2—H2O⋯O1	0.84	2.01	2.755 (6)	147

Symmetry code: (i) .