2-Ethyl-3-[(R)-2-phenyl-butanamido]-quinazolin-4(3H)-one monohydrate.

In the title compound, C20H21N3O2·H2O (EQR·H2O), the quinazoline ring system forms dihedral angles of 53.1 (1) and 85.6 (1)° with the phenyl ring and the amide link, respectively. In the crystal, O-H⋯O hydrogen bonds link two EQR and two water mol-ecules into a centrosymmetric R 4 (4)(18) ring motif. N-H⋯O hydrogen bonds further link these hydrogen-bonded fragments into columns extending in [010].

Related literature

For convenient routes towards modifying 3H-quinazolin-4-one derivatives, see: Smith et al. (1995 ▶, 1996a ▶,b ▶, 2004 ▶). For the crystal structures of related compounds, see: Yang et al. (2009 ▶); Srinivasan et al. (2011 ▶).

Experimental

Crystal data

C20H21N3O2·n class="Chemical">H2O

M = 353.41

Monoclinic,

a = 14.5354 (2) Å

b = 7.3529 (1) Å

c = 18.1945 (3) Å

β = 98.591 (1)°

V = 1922.76 (5) Å3

Z = 4

Cu Kα radiation

μ = 0.68 mm−1

T = 296 K

0.41 × 0.21 × 0.08 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer

Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014 ▶) T min = 0.723, T max = 1.000

13383 measured reflections

3796 independent reflections

3341 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.116

S = 1.05

3796 reflections

246 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.36 e Å−3

Data collection: CrysAlis PRO (Agilent, 2014 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and CHEMDRAW Ultra (CambridgeSoft, 2001 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814005996/cv5446sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814005996/cv5446Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814005996/cv5446Isup3.cml

CCDC reference: 992297

Additional supporting information: crystallographic information; 3D view; checkCIF report

C20H21N3O2·H2O	F(000) = 752
Mr = 353.41	Dx = 1.221 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 14.5354 (2) Å	Cell parameters from 3341 reflections
b = 7.3529 (1) Å	θ = 3.6–67.7°
c = 18.1945 (3) Å	µ = 0.68 mm−1
β = 98.591 (1)°	T = 296 K
V = 1922.76 (5) Å3	Plate, colourless
Z = 4	0.41 × 0.21 × 0.08 mm

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	3341 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube	Rint = 0.017
ω scans	θmax = 73.5°, θmin = 3.6°
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014)	h = −16→17
Tmin = 0.723, Tmax = 1.000	k = −9→8
13383 measured reflections	l = −22→21
3796 independent reflections

Refinement on F2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.040	w = 1/[σ2(Fo2) + (0.0544P)2 + 0.3851P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.116	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.29 e Å−3
3796 reflections	Δρmin = −0.36 e Å−3
246 parameters	Extinction correction: SHELXL2013 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0033 (3)

Experimental. Absorption correction: CrysAlisPro (Agilent, 2014): Numerical absorption correction based on Gaussian integration over a multifaceted crystal model. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

	x	y	z	Uiso*/Ueq
C1	0.71716 (9)	0.66803 (17)	0.06334 (7)	0.0466 (3)
C2	0.81747 (9)	0.69215 (18)	0.07879 (8)	0.0525 (3)
C3	0.85958 (9)	0.72040 (19)	0.15199 (9)	0.0557 (3)
C4	0.72196 (9)	0.69526 (17)	0.19860 (7)	0.0470 (3)
C5	0.87036 (12)	0.6905 (3)	0.02072 (11)	0.0732 (5)
H5	0.8418	0.6688	−0.0277	0.088*
C6	0.96387 (14)	0.7207 (3)	0.03496 (15)	0.0952 (7)
H6	0.9992	0.7205	−0.0037	0.114*
C7	1.00601 (13)	0.7517 (3)	0.10751 (16)	0.0979 (7)
H7	1.0697	0.7731	0.1168	0.117*
C8	0.95599 (11)	0.7514 (3)	0.16581 (13)	0.0796 (5)
H8	0.9857	0.7715	0.2140	0.096*
C9	0.52278 (8)	0.79347 (16)	0.10850 (7)	0.0410 (3)
C10	0.41982 (8)	0.74708 (17)	0.10069 (7)	0.0418 (3)
H10	0.4092	0.6357	0.0711	0.050*
C11	0.39529 (8)	0.70884 (18)	0.17738 (7)	0.0456 (3)
C12	0.34870 (10)	0.5513 (2)	0.19121 (8)	0.0593 (4)
H12	0.3334	0.4666	0.1534	0.071*
C13	0.32464 (13)	0.5187 (3)	0.26100 (10)	0.0781 (5)
H13	0.2928	0.4128	0.2695	0.094*
C14	0.34730 (15)	0.6408 (3)	0.31718 (10)	0.0835 (5)
H14	0.3308	0.6185	0.3638	0.100*
C15	0.39456 (14)	0.7967 (3)	0.30473 (9)	0.0769 (5)
H15	0.4110	0.8791	0.3432	0.092*
C16	0.41781 (11)	0.8314 (2)	0.23522 (8)	0.0600 (4)
H16	0.4490	0.9383	0.2271	0.072*
C17	0.66472 (11)	0.6937 (2)	0.26021 (8)	0.0611 (4)
H17A	0.6266	0.5848	0.2559	0.073*
H17B	0.6232	0.7977	0.2545	0.073*
C18	0.72124 (14)	0.6992 (3)	0.33713 (9)	0.0749 (5)
H18A	0.7599	0.5929	0.3445	0.112*
H18B	0.6800	0.7021	0.3737	0.112*
H18C	0.7597	0.8060	0.3419	0.112*
C19	0.35937 (9)	0.8981 (2)	0.06048 (7)	0.0512 (3)
H19A	0.3635	1.0057	0.0916	0.061*
H19B	0.3826	0.9292	0.0148	0.061*
C20	0.25831 (10)	0.8397 (2)	0.04242 (9)	0.0628 (4)
H20A	0.2540	0.7337	0.0113	0.094*
H20B	0.2224	0.9364	0.0169	0.094*
H20C	0.2346	0.8119	0.0876	0.094*
N1	0.81045 (8)	0.72053 (16)	0.21145 (7)	0.0557 (3)
N2	0.67465 (7)	0.66873 (14)	0.12675 (6)	0.0429 (2)
N3	0.57841 (7)	0.64529 (14)	0.11660 (6)	0.0446 (3)
H3	0.5547	0.5380	0.1155	0.054*
O1	0.67227 (7)	0.64818 (15)	0.00151 (5)	0.0613 (3)
O2	0.55448 (6)	0.94696 (12)	0.11169 (6)	0.0557 (3)
O3	0.50861 (9)	0.30699 (16)	0.07666 (10)	0.0873 (5)
H3A	0.5189 (19)	0.193 (4)	0.0963 (14)	0.124 (9)*
H3B	0.450 (2)	0.306 (4)	0.0514 (15)	0.123 (9)*

	U11	U22	U33	U12	U13	U23
C1	0.0444 (6)	0.0406 (6)	0.0543 (7)	0.0049 (5)	0.0061 (5)	0.0001 (5)
C2	0.0436 (7)	0.0456 (7)	0.0687 (8)	0.0041 (5)	0.0100 (6)	0.0023 (6)
C3	0.0412 (7)	0.0474 (7)	0.0766 (9)	0.0026 (5)	0.0032 (6)	0.0011 (6)
C4	0.0482 (7)	0.0384 (6)	0.0518 (7)	0.0015 (5)	−0.0008 (5)	0.0040 (5)
C5	0.0592 (9)	0.0781 (11)	0.0871 (12)	0.0042 (8)	0.0264 (8)	−0.0011 (9)
C6	0.0634 (11)	0.1038 (16)	0.1273 (19)	−0.0029 (10)	0.0433 (12)	−0.0105 (14)
C7	0.0429 (9)	0.1033 (15)	0.151 (2)	−0.0051 (9)	0.0268 (11)	−0.0150 (15)
C8	0.0432 (8)	0.0802 (12)	0.1115 (15)	−0.0009 (8)	−0.0010 (8)	−0.0100 (10)
C9	0.0421 (6)	0.0375 (6)	0.0439 (6)	0.0001 (5)	0.0077 (5)	0.0028 (5)
C10	0.0387 (6)	0.0418 (6)	0.0451 (6)	−0.0001 (5)	0.0069 (5)	0.0000 (5)
C11	0.0392 (6)	0.0504 (7)	0.0473 (6)	−0.0002 (5)	0.0070 (5)	0.0036 (5)
C12	0.0591 (8)	0.0608 (9)	0.0582 (8)	−0.0127 (7)	0.0088 (6)	0.0058 (7)
C13	0.0840 (12)	0.0812 (12)	0.0721 (10)	−0.0192 (9)	0.0212 (9)	0.0191 (9)
C14	0.1001 (14)	0.0986 (14)	0.0564 (9)	−0.0080 (11)	0.0265 (9)	0.0127 (9)
C15	0.0934 (13)	0.0861 (12)	0.0536 (9)	−0.0062 (10)	0.0185 (8)	−0.0089 (8)
C16	0.0655 (9)	0.0603 (9)	0.0561 (8)	−0.0090 (7)	0.0157 (7)	−0.0048 (6)
C17	0.0644 (9)	0.0651 (9)	0.0533 (8)	0.0004 (7)	0.0074 (6)	0.0071 (7)
C18	0.0978 (13)	0.0720 (11)	0.0522 (8)	−0.0035 (9)	0.0023 (8)	0.0017 (7)
C19	0.0465 (7)	0.0560 (8)	0.0516 (7)	0.0083 (6)	0.0096 (5)	0.0071 (6)
C20	0.0473 (7)	0.0793 (10)	0.0590 (8)	0.0111 (7)	−0.0012 (6)	−0.0030 (7)
N1	0.0464 (6)	0.0538 (7)	0.0627 (7)	0.0000 (5)	−0.0057 (5)	0.0015 (5)
N2	0.0356 (5)	0.0398 (5)	0.0521 (6)	0.0007 (4)	0.0025 (4)	0.0010 (4)
N3	0.0350 (5)	0.0363 (5)	0.0618 (6)	−0.0024 (4)	0.0046 (4)	0.0000 (4)
O1	0.0554 (6)	0.0734 (7)	0.0533 (6)	0.0040 (5)	0.0022 (4)	−0.0047 (5)
O2	0.0473 (5)	0.0367 (5)	0.0830 (7)	−0.0019 (4)	0.0092 (4)	0.0053 (4)
O3	0.0695 (8)	0.0397 (6)	0.1395 (13)	−0.0015 (5)	−0.0278 (8)	−0.0025 (6)

C1—O1	1.2220 (16)	C12—C13	1.387 (2)
C1—N2	1.3879 (17)	C12—H12	0.9300
C1—C2	1.4539 (18)	C13—C14	1.364 (3)
C2—C3	1.396 (2)	C13—H13	0.9300
C2—C5	1.397 (2)	C14—C15	1.372 (3)
C3—N1	1.382 (2)	C14—H14	0.9300
C3—C8	1.405 (2)	C15—C16	1.381 (2)
C4—N1	1.2860 (17)	C15—H15	0.9300
C4—N2	1.3969 (16)	C16—H16	0.9300
C4—C17	1.493 (2)	C17—C18	1.514 (2)
C5—C6	1.363 (3)	C17—H17A	0.9700
C5—H5	0.9300	C17—H17B	0.9700
C6—C7	1.389 (3)	C18—H18A	0.9600
C6—H6	0.9300	C18—H18B	0.9600
C7—C8	1.373 (3)	C18—H18C	0.9600
C7—H7	0.9300	C19—C20	1.519 (2)
C8—H8	0.9300	C19—H19A	0.9700
C9—O2	1.2172 (15)	C19—H19B	0.9700
C9—N3	1.3516 (16)	C20—H20A	0.9600
C9—C10	1.5208 (16)	C20—H20B	0.9600
C10—C11	1.5171 (17)	C20—H20C	0.9600
C10—C19	1.5324 (17)	N2—N3	1.3941 (14)
C10—H10	0.9800	N3—H3	0.8600
C11—C12	1.3836 (19)	O3—H3A	0.92 (3)
C11—C16	1.387 (2)	O3—H3B	0.91 (3)
O1—C1—N2	121.53 (12)	C13—C14—C15	119.81 (16)
O1—C1—C2	125.08 (13)	C13—C14—H14	120.1
N2—C1—C2	113.39 (12)	C15—C14—H14	120.1
C3—C2—C5	120.71 (14)	C14—C15—C16	120.18 (17)
C3—C2—C1	119.13 (13)	C14—C15—H15	119.9
C5—C2—C1	120.14 (14)	C16—C15—H15	119.9
N1—C3—C2	122.86 (12)	C15—C16—C11	120.84 (15)
N1—C3—C8	118.55 (15)	C15—C16—H16	119.6
C2—C3—C8	118.58 (16)	C11—C16—H16	119.6
N1—C4—N2	121.97 (13)	C4—C17—C18	114.06 (14)
N1—C4—C17	121.28 (12)	C4—C17—H17A	108.7
N2—C4—C17	116.75 (11)	C18—C17—H17A	108.7
C6—C5—C2	120.05 (19)	C4—C17—H17B	108.7
C6—C5—H5	120.0	C18—C17—H17B	108.7
C2—C5—H5	120.0	H17A—C17—H17B	107.6
C5—C6—C7	119.54 (19)	C17—C18—H18A	109.5
C5—C6—H6	120.2	C17—C18—H18B	109.5
C7—C6—H6	120.2	H18A—C18—H18B	109.5
C8—C7—C6	121.67 (17)	C17—C18—H18C	109.5
C8—C7—H7	119.2	H18A—C18—H18C	109.5
C6—C7—H7	119.2	H18B—C18—H18C	109.5
C7—C8—C3	119.43 (19)	C20—C19—C10	111.44 (12)
C7—C8—H8	120.3	C20—C19—H19A	109.3
C3—C8—H8	120.3	C10—C19—H19A	109.3
O2—C9—N3	121.75 (11)	C20—C19—H19B	109.3
O2—C9—C10	124.94 (11)	C10—C19—H19B	109.3
N3—C9—C10	113.18 (10)	H19A—C19—H19B	108.0
C11—C10—C9	108.59 (10)	C19—C20—H20A	109.5
C11—C10—C19	112.12 (10)	C19—C20—H20B	109.5
C9—C10—C19	111.61 (10)	H20A—C20—H20B	109.5
C11—C10—H10	108.1	C19—C20—H20C	109.5
C9—C10—H10	108.1	H20A—C20—H20C	109.5
C19—C10—H10	108.1	H20B—C20—H20C	109.5
C12—C11—C16	118.18 (13)	C4—N1—C3	118.51 (12)
C12—C11—C10	120.74 (12)	C1—N2—N3	116.87 (10)
C16—C11—C10	121.08 (12)	C1—N2—C4	124.09 (11)
C11—C12—C13	120.56 (15)	N3—N2—C4	119.02 (10)
C11—C12—H12	119.7	C9—N3—N2	119.14 (10)
C13—C12—H12	119.7	C9—N3—H3	120.4
C14—C13—C12	120.43 (16)	N2—N3—H3	120.4
C14—C13—H13	119.8	H3A—O3—H3B	106 (2)
C12—C13—H13	119.8

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O3	0.86	1.92	2.7431 (15)	159
O3—H3A···O2i	0.92 (3)	1.89 (3)	2.7806 (15)	164 (2)
O3—H3B···O1ii	0.91 (3)	1.92 (3)	2.8154 (17)	169 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O3	0.86	1.92	2.7431 (15)	159
O3—H3A⋯O2i	0.92 (3)	1.89 (3)	2.7806 (15)	164 (2)
O3—H3B⋯O1ii	0.91 (3)	1.92 (3)	2.8154 (17)	169 (2)

Symmetry codes: (i) ; (ii) .