4-(4-{[(2-Phenyl-quinazolin-4-yl)-oxy]methyl}-1H-1,2,3-triazol-1-yl)butan-1-ol hemihydrate.

The title compound, C(21)H(21)N(5)O(2)·0.5H(2)O, has two fused six-membered rings linked to a benzene ring and to a triazole ring, which is connected to a butanol group. The quinazoline ring forms a dihedral angle of 7.88 (8)° with the benzene ring, while the triazole ring is approximately perpendicular to the benzene ring and to the quinazoline system, making dihedral angles of 84.38 (10) and 76.55 (8)°, respectively. The stereochemical arrangement of the butanol chain, with a C-C-C-C torsion angle of 178.34 (19)°, corresponds to an anti-periplanar conformation. However the position of the -OH group is split into two very close [O-O = 0.810(3) Å] positions of equal occupancy. The crystal structure features O-H⋯N and O-H⋯O hydrogen bonds, building an infinite three-dimensional network. The water molecule is located on a half-filled general position.

Related literature

For details of the synthesis, see: Krim et al. (2009 ▶); Mani Chandrika et al. (2010 ▶). For the biological activity of quinazolinone derivatives, see: Alvarez et al. (1994 ▶); Chan et al. (1997 ▶); De Clercq (1997 ▶, 2002 ▶); Dempcy & Skibo (1991 ▶); Gackenheimer et al. (1995 ▶).

Experimental

Crystal data

C21H21N5O2·0.5H2O

M = 384.44

Monoclinic,

a = 11.359 (4) Å

b = 7.694 (3) Å

c = 22.817 (7) Å

β = 101.111 (16)°

V = 1956.9 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.55 × 0.31 × 0.28 mm

Data collection

Bruker X8 APEX Diffractometer

18195 measured reflections

3709 independent reflections

2879 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.127

S = 1.03

3709 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia,1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811027280/fj2442sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027280/fj2442Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811027280/fj2442Isup3.cml

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

C21H21N5O2·0.5H2O	F(000) = 812
Mr = 384.44	Dx = 1.305 Mg m−3
Monoclinic, P21/n	Melting point: 371(1) K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 11.359 (4) Å	Cell parameters from 3709 reflections
b = 7.694 (3) Å	θ = 1.8–25.7°
c = 22.817 (7) Å	µ = 0.09 mm−1
β = 101.111 (16)°	T = 296 K
V = 1956.9 (12) Å3	Block, colourless
Z = 4	0.55 × 0.31 × 0.28 mm

Bruker X8 APEX Diffractometer	2879 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
graphite	θmax = 25.7°, θmin = 1.8°
φ and ω scans	h = −13→13
18195 measured reflections	k = −9→9
3709 independent reflections	l = −27→27

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0668P)2 + 0.4064P] where P = (Fo2 + 2Fc2)/3
3709 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.58474 (13)	0.7779 (2)	−0.02725 (7)	0.0442 (4)
C2	0.69772 (15)	0.8512 (2)	−0.00495 (8)	0.0548 (4)
H2	0.7529	0.8648	−0.0299	0.066*
C3	0.72682 (16)	0.9027 (2)	0.05374 (8)	0.0588 (5)
H3	0.8021	0.9503	0.0682	0.071*
C4	0.64558 (16)	0.8851 (2)	0.09214 (8)	0.0587 (5)
H4	0.6669	0.9205	0.1317	0.070*
C5	0.53502 (15)	0.8160 (2)	0.07146 (7)	0.0515 (4)
H5	0.4806	0.8044	0.0969	0.062*
C6	0.50330 (13)	0.7621 (2)	0.01149 (6)	0.0416 (3)
C7	0.39026 (13)	0.69043 (19)	−0.01484 (6)	0.0410 (3)
C8	0.45066 (13)	0.6516 (2)	−0.10360 (6)	0.0424 (4)
C9	0.41915 (14)	0.5786 (2)	−0.16527 (6)	0.0446 (4)
C10	0.49525 (17)	0.5955 (3)	−0.20563 (8)	0.0595 (5)
H10	0.5673	0.6552	−0.1945	0.071*
C11	0.46526 (19)	0.5245 (3)	−0.26255 (8)	0.0692 (5)
H11	0.5167	0.5390	−0.2893	0.083*
C12	0.36108 (19)	0.4337 (3)	−0.27949 (8)	0.0634 (5)
H12	0.3415	0.3852	−0.3175	0.076*
C13	0.28553 (18)	0.4149 (3)	−0.23962 (8)	0.0630 (5)
H13	0.2146	0.3525	−0.2507	0.076*
C14	0.31353 (16)	0.4879 (2)	−0.18315 (7)	0.0543 (4)
H14	0.2606	0.4756	−0.1570	0.065*
C15	0.19503 (14)	0.6055 (2)	−0.00380 (7)	0.0499 (4)
H15A	0.2048	0.4910	−0.0200	0.060*
H15B	0.1522	0.6786	−0.0355	0.060*
C16	0.12872 (13)	0.5943 (2)	0.04624 (6)	0.0432 (4)
C17	0.14267 (15)	0.4820 (2)	0.09333 (7)	0.0537 (4)
H17	0.1969	0.3905	0.1013	0.064*
C18	0.04037 (17)	0.4596 (3)	0.18224 (8)	0.0743 (6)
H18A	0.0219	0.3369	0.1770	0.089*
H18B	−0.0289	0.5169	0.1926	0.089*
C19	0.14564 (16)	0.4819 (3)	0.23258 (7)	0.0575 (4)
H19A	0.1675	0.6038	0.2357	0.069*
H19B	0.2133	0.4180	0.2232	0.069*
C20	0.12258 (18)	0.4201 (3)	0.29266 (8)	0.0660 (5)
H20A	0.0564	0.4864	0.3026	0.079*
H20B	0.0984	0.2991	0.2892	0.079*
C21	0.22746 (19)	0.4373 (3)	0.34201 (8)	0.0667 (5)
H21A	0.2128	0.3960	0.3807	0.080*
H21B	0.2987	0.3722	0.3308	0.080*
N1	0.55697 (11)	0.72071 (18)	−0.08592 (6)	0.0481 (3)
N2	0.36315 (11)	0.63662 (16)	−0.07008 (5)	0.0433 (3)
N3	0.04075 (12)	0.7060 (2)	0.05220 (6)	0.0568 (4)
N4	0.00007 (13)	0.6671 (2)	0.10089 (6)	0.0631 (4)
N5	0.06216 (12)	0.5313 (2)	0.12552 (6)	0.0540 (4)
O1	0.31014 (9)	0.68013 (15)	0.02114 (4)	0.0493 (3)
O2A	0.2984 (3)	0.5903 (4)	0.34478 (14)	0.0678 (8)	0.50
H2A	0.3564	0.5896	0.3752	0.081*	0.50
O2B	0.2355 (3)	0.6236 (4)	0.35259 (13)	0.0616 (8)	0.50
H2B	0.1784	0.6580	0.3697	0.074*	0.50
O3W	0.0201 (2)	1.0729 (4)	0.05595 (13)	0.0792 (8)	0.50
H3WA	−0.0015	1.1217	0.0217	0.095*	0.50
H3WB	0.0313	0.9655	0.0481	0.095*	0.50

	U11	U22	U33	U12	U13	U23
C1	0.0447 (8)	0.0407 (9)	0.0462 (8)	0.0067 (6)	0.0062 (6)	0.0023 (7)
C2	0.0434 (9)	0.0597 (11)	0.0609 (10)	0.0016 (8)	0.0092 (7)	−0.0004 (8)
C3	0.0467 (9)	0.0602 (11)	0.0643 (11)	−0.0007 (8)	−0.0026 (8)	−0.0035 (9)
C4	0.0594 (10)	0.0640 (12)	0.0470 (9)	0.0002 (9)	−0.0041 (8)	−0.0056 (8)
C5	0.0548 (9)	0.0556 (10)	0.0429 (8)	0.0008 (8)	0.0067 (7)	−0.0014 (7)
C6	0.0447 (8)	0.0378 (8)	0.0408 (8)	0.0048 (6)	0.0049 (6)	0.0025 (6)
C7	0.0479 (8)	0.0376 (8)	0.0382 (7)	0.0029 (6)	0.0096 (6)	0.0020 (6)
C8	0.0471 (8)	0.0405 (8)	0.0400 (8)	0.0064 (7)	0.0092 (6)	0.0020 (6)
C9	0.0518 (9)	0.0414 (9)	0.0403 (8)	0.0083 (7)	0.0078 (7)	0.0021 (6)
C10	0.0617 (10)	0.0690 (12)	0.0508 (9)	−0.0010 (9)	0.0181 (8)	−0.0074 (8)
C11	0.0792 (13)	0.0847 (14)	0.0489 (10)	0.0080 (11)	0.0252 (9)	−0.0078 (9)
C12	0.0784 (13)	0.0665 (12)	0.0417 (9)	0.0188 (10)	0.0021 (8)	−0.0097 (8)
C13	0.0666 (11)	0.0667 (12)	0.0516 (10)	0.0004 (9)	0.0010 (8)	−0.0113 (9)
C14	0.0573 (10)	0.0598 (11)	0.0455 (9)	0.0004 (8)	0.0091 (7)	−0.0027 (8)
C15	0.0498 (9)	0.0581 (10)	0.0409 (8)	−0.0092 (8)	0.0066 (7)	−0.0037 (7)
C16	0.0429 (8)	0.0453 (9)	0.0398 (8)	−0.0046 (7)	0.0042 (6)	−0.0028 (6)
C17	0.0592 (10)	0.0535 (10)	0.0498 (9)	0.0066 (8)	0.0137 (8)	0.0050 (8)
C18	0.0621 (11)	0.1113 (18)	0.0518 (10)	−0.0189 (11)	0.0168 (9)	0.0169 (11)
C19	0.0615 (10)	0.0667 (12)	0.0471 (9)	−0.0035 (9)	0.0174 (8)	0.0035 (8)
C20	0.0722 (12)	0.0760 (13)	0.0528 (10)	−0.0031 (10)	0.0194 (9)	0.0104 (9)
C21	0.0831 (13)	0.0668 (13)	0.0500 (10)	−0.0079 (10)	0.0121 (9)	0.0081 (9)
N1	0.0473 (7)	0.0531 (8)	0.0446 (7)	0.0027 (6)	0.0108 (6)	−0.0013 (6)
N2	0.0485 (7)	0.0420 (7)	0.0393 (7)	0.0009 (6)	0.0082 (5)	−0.0011 (5)
N3	0.0527 (8)	0.0646 (10)	0.0523 (8)	0.0077 (7)	0.0081 (6)	0.0070 (7)
N4	0.0480 (8)	0.0879 (12)	0.0544 (8)	0.0095 (8)	0.0121 (7)	0.0051 (8)
N5	0.0463 (7)	0.0714 (10)	0.0442 (7)	−0.0060 (7)	0.0086 (6)	0.0057 (7)
O1	0.0495 (6)	0.0605 (7)	0.0392 (5)	−0.0108 (5)	0.0118 (5)	−0.0065 (5)
O2A	0.076 (2)	0.067 (2)	0.0591 (17)	−0.0163 (18)	0.0112 (16)	−0.0002 (14)
O2B	0.0581 (18)	0.073 (2)	0.0571 (16)	−0.0114 (16)	0.0198 (14)	−0.0072 (13)
O3W	0.0685 (17)	0.0626 (18)	0.098 (2)	0.0057 (13)	−0.0061 (15)	0.0313 (15)

C1—N1	1.387 (2)	C15—O1	1.4409 (19)
C1—C6	1.402 (2)	C15—C16	1.487 (2)
C1—C2	1.404 (2)	C15—H15A	0.9700
C2—C3	1.375 (2)	C15—H15B	0.9700
C2—H2	0.9300	C16—N3	1.345 (2)
C3—C4	1.396 (3)	C16—C17	1.364 (2)
C3—H3	0.9300	C17—N5	1.333 (2)
C4—C5	1.362 (2)	C17—H17	0.9300
C4—H4	0.9300	C18—N5	1.471 (2)
C5—C6	1.409 (2)	C18—C19	1.500 (3)
C5—H5	0.9300	C18—H18A	0.9700
C6—C7	1.420 (2)	C18—H18B	0.9700
C7—N2	1.3058 (19)	C19—C20	1.520 (2)
C7—O1	1.3404 (17)	C19—H19A	0.9700
C8—N1	1.310 (2)	C19—H19B	0.9700
C8—N2	1.3710 (19)	C20—C21	1.479 (3)
C8—C9	1.493 (2)	C20—H20A	0.9700
C9—C14	1.380 (2)	C20—H20B	0.9700
C9—C10	1.385 (2)	C21—O2A	1.421 (4)
C10—C11	1.390 (3)	C21—O2B	1.453 (4)
C10—H10	0.9300	C21—H21A	0.9822
C11—C12	1.364 (3)	C21—H21B	1.0253
C11—H11	0.9300	N3—N4	1.3171 (19)
C12—C13	1.373 (3)	N4—N5	1.324 (2)
C12—H12	0.9300	O2A—H2A	0.8601
C13—C14	1.385 (2)	O2B—H2B	0.8600
C13—H13	0.9300	O3W—H3WA	0.8599
C14—H14	0.9300	O3W—H3WB	0.8599
N1—C1—C6	121.74 (14)	N3—C16—C17	107.52 (14)
N1—C1—C2	119.95 (14)	N3—C16—C15	122.48 (14)
C6—C1—C2	118.30 (14)	C17—C16—C15	129.99 (15)
C3—C2—C1	120.02 (16)	N5—C17—C16	105.43 (15)
C3—C2—H2	120.0	N5—C17—H17	127.3
C1—C2—H2	120.0	C16—C17—H17	127.3
C2—C3—C4	121.30 (16)	N5—C18—C19	112.75 (15)
C2—C3—H3	119.4	N5—C18—H18A	109.0
C4—C3—H3	119.4	C19—C18—H18A	109.0
C5—C4—C3	119.83 (16)	N5—C18—H18B	109.0
C5—C4—H4	120.1	C19—C18—H18B	109.0
C3—C4—H4	120.1	H18A—C18—H18B	107.8
C4—C5—C6	119.86 (15)	C18—C19—C20	113.86 (15)
C4—C5—H5	120.1	C18—C19—H19A	108.8
C6—C5—H5	120.1	C20—C19—H19A	108.8
C1—C6—C5	120.69 (15)	C18—C19—H19B	108.8
C1—C6—C7	114.81 (13)	C20—C19—H19B	108.8
C5—C6—C7	124.51 (14)	H19A—C19—H19B	107.7
N2—C7—O1	120.72 (14)	C21—C20—C19	113.89 (16)
N2—C7—C6	123.86 (13)	C21—C20—H20A	108.8
O1—C7—C6	115.42 (12)	C19—C20—H20A	108.8
N1—C8—N2	125.94 (14)	C21—C20—H20B	108.8
N1—C8—C9	118.83 (13)	C19—C20—H20B	108.8
N2—C8—C9	115.22 (13)	H20A—C20—H20B	107.7
C14—C9—C10	118.00 (15)	O2A—C21—C20	118.3 (2)
C14—C9—C8	120.39 (14)	O2B—C21—C20	103.3 (2)
C10—C9—C8	121.60 (15)	O2A—C21—H21A	114.9
C9—C10—C11	120.82 (18)	O2B—C21—H21A	100.7
C9—C10—H10	119.6	C20—C21—H21A	113.8
C11—C10—H10	119.6	O2A—C21—H21B	87.0
C12—C11—C10	120.60 (17)	O2B—C21—H21B	119.7
C12—C11—H11	119.7	C20—C21—H21B	108.9
C10—C11—H11	119.7	H21A—C21—H21B	110.2
C11—C12—C13	119.00 (16)	C8—N1—C1	116.79 (13)
C11—C12—H12	120.5	C7—N2—C8	116.77 (13)
C13—C12—H12	120.5	N4—N3—C16	109.17 (14)
C12—C13—C14	120.86 (18)	N3—N4—N5	107.01 (13)
C12—C13—H13	119.6	N4—N5—C17	110.87 (13)
C14—C13—H13	119.6	N4—N5—C18	120.20 (15)
C9—C14—C13	120.70 (16)	C17—N5—C18	128.88 (17)
C9—C14—H14	119.6	C7—O1—C15	116.95 (11)
C13—C14—H14	119.6	O2B—O2A—C21	75.9 (4)
O1—C15—C16	105.98 (12)	O2B—O2A—H2A	113.3
O1—C15—H15A	110.5	C21—O2A—H2A	111.7
C16—C15—H15A	110.5	C21—O2B—H2A	84.4
O1—C15—H15B	110.5	C21—O2B—H2B	110.5
C16—C15—H15B	110.5	H3WA—O3W—H3WB	105.0
H15A—C15—H15B	108.7
N1—C1—C2—C3	−177.89 (16)	N3—C16—C17—N5	0.08 (18)
C6—C1—C2—C3	1.0 (2)	C15—C16—C17—N5	178.72 (15)
C1—C2—C3—C4	−0.5 (3)	N5—C18—C19—C20	176.04 (18)
C2—C3—C4—C5	−0.1 (3)	C18—C19—C20—C21	178.34 (19)
C3—C4—C5—C6	0.2 (3)	C19—C20—C21—O2A	41.2 (3)
N1—C1—C6—C5	177.93 (15)	C19—C20—C21—O2B	72.5 (2)
C2—C1—C6—C5	−1.0 (2)	N2—C8—N1—C1	2.5 (2)
N1—C1—C6—C7	−2.5 (2)	C9—C8—N1—C1	−176.43 (13)
C2—C1—C6—C7	178.63 (14)	C6—C1—N1—C8	0.2 (2)
C4—C5—C6—C1	0.4 (2)	C2—C1—N1—C8	179.13 (15)
C4—C5—C6—C7	−179.21 (16)	O1—C7—N2—C8	−179.81 (13)
C1—C6—C7—N2	2.3 (2)	C6—C7—N2—C8	0.0 (2)
C5—C6—C7—N2	−178.07 (15)	N1—C8—N2—C7	−2.7 (2)
C1—C6—C7—O1	−177.81 (13)	C9—C8—N2—C7	176.30 (13)
C5—C6—C7—O1	1.8 (2)	C17—C16—N3—N4	−0.03 (19)
N1—C8—C9—C14	172.80 (15)	C15—C16—N3—N4	−178.79 (14)
N2—C8—C9—C14	−6.3 (2)	C16—N3—N4—N5	−0.04 (19)
N1—C8—C9—C10	−5.6 (2)	N3—N4—N5—C17	0.09 (19)
N2—C8—C9—C10	175.30 (15)	N3—N4—N5—C18	177.93 (15)
C14—C9—C10—C11	0.6 (3)	C16—C17—N5—N4	−0.10 (19)
C8—C9—C10—C11	179.04 (17)	C16—C17—N5—C18	−177.71 (16)
C9—C10—C11—C12	−1.2 (3)	C19—C18—N5—N4	−113.8 (2)
C10—C11—C12—C13	0.7 (3)	C19—C18—N5—C17	63.6 (3)
C11—C12—C13—C14	0.5 (3)	N2—C7—O1—C15	0.8 (2)
C10—C9—C14—C13	0.6 (3)	C6—C7—O1—C15	−179.06 (13)
C8—C9—C14—C13	−177.90 (15)	C16—C15—O1—C7	174.82 (12)
C12—C13—C14—C9	−1.1 (3)	C20—C21—O2A—O2B	69.2 (4)
O1—C15—C16—N3	103.78 (17)	C20—C21—O2B—O2A	−122.3 (4)
O1—C15—C16—C17	−74.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2B—H2B···N1i	0.86	2.08	2.935 (3)	170
O2A—H2A···O3Wii	0.86	1.90	2.757 (4)	176
O3W—H3WA···N3iii	0.86	2.12	2.967 (3)	167
O3W—H3WB···N3	0.86	2.00	2.835 (3)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2B—H2B⋯N1i	0.86	2.08	2.935 (3)	170
O2A—H2A⋯O3Wii	0.86	1.90	2.757 (4)	176
O3W—H3WA⋯N3iii	0.86	2.12	2.967 (3)	167
O3W—H3WB⋯N3	0.86	2.00	2.835 (3)	163

Symmetry codes: (i) ; (ii) ; (iii) .