2-(2,4,5-Trimeth-oxy-phen-yl)-2,3-dihydro-quinolin-4(1H)-one.

In the title aza-flavanone, C(18)H(19)NO(4), an intra-molecular cyclization product of chalcone, the central heterocyclic ring is in an envelope conformation and the dihedral angle between the benzene rings is 51.03 (10)°. The meth-oxy groups at the ortho and para positions are slightly twisted from the benzene ring to which they are bound [C-O-C-C = 21.9 (3) and -171.93 (18)°, respectively], whereas the meth-oxy group at the meta position is almost coplanar [C-O-C-C = 3.5 (3)°]. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds and weak C-H⋯O inter-actions into chains along the [001] direction. Weak C-H⋯π inter-actions also occur.

Related literature

For background to the syntheses and properties of aza-flavanones, see: Göker et al. (2005 ▶); Xia et al. (1998 ▶). For ring conformations, see Cremer & Pople (1975 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C18H19NO4

M = 313.34

Monoclinic,

a = 10.7354 (11) Å

b = 17.1525 (16) Å

c = 8.6471 (8) Å

β = 102.981 (2)°

V = 1551.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.41 × 0.16 × 0.06 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.962, T max = 0.994

13335 measured reflections

4511 independent reflections

2751 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.156

S = 1.03

4511 reflections

215 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812002917/hb6602sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002917/hb6602Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812002917/hb6602Isup3.cml

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

C18H19NO4	F(000) = 664
Mr = 313.34	Dx = 1.341 Mg m−3
Monoclinic, P21/c	Melting point = 419–420 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.7354 (11) Å	Cell parameters from 4511 reflections
b = 17.1525 (16) Å	θ = 2.0–30.0°
c = 8.6471 (8) Å	µ = 0.10 mm−1
β = 102.981 (2)°	T = 100 K
V = 1551.6 (3) Å3	Needle, yellow
Z = 4	0.41 × 0.16 × 0.06 mm

Bruker APEXII CCD diffractometer	4511 independent reflections
Radiation source: sealed tube	2751 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.062
φ and ω scans	θmax = 30.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→15
Tmin = 0.962, Tmax = 0.994	k = −20→24
13335 measured reflections	l = −12→12

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0535P)2 + 0.8134P] where P = (Fo2 + 2Fc2)/3
4511 reflections	(Δ/σ)max = 0.001
215 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K.

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
O1	0.37635 (19)	0.62888 (9)	0.70678 (18)	0.0317 (4)
O2	0.04382 (17)	0.43778 (8)	0.70161 (18)	0.0258 (4)
O3	0.06325 (15)	0.15459 (8)	0.69306 (16)	0.0186 (3)
O4	0.25884 (15)	0.16149 (8)	0.56105 (17)	0.0190 (3)
N1	0.2864 (2)	0.44806 (10)	0.3926 (2)	0.0188 (4)
C1	0.3224 (2)	0.51866 (11)	0.3388 (2)	0.0169 (4)
C2	0.3287 (2)	0.52803 (12)	0.1791 (3)	0.0200 (5)
H2A	0.3127	0.4847	0.1091	0.024*
C3	0.3577 (2)	0.59951 (13)	0.1230 (3)	0.0227 (5)
H3A	0.3602	0.6050	0.0144	0.027*
C4	0.3837 (2)	0.66416 (13)	0.2242 (3)	0.0261 (5)
H4A	0.4023	0.7135	0.1847	0.031*
C5	0.3817 (2)	0.65508 (13)	0.3821 (3)	0.0253 (5)
H5A	0.4008	0.6984	0.4517	0.030*
C6	0.3519 (2)	0.58298 (12)	0.4419 (2)	0.0193 (5)
C7	0.3519 (2)	0.57481 (12)	0.6125 (3)	0.0210 (5)
C8	0.3224 (2)	0.49397 (12)	0.6637 (2)	0.0206 (5)
H8A	0.2854	0.4977	0.7585	0.025*
H8B	0.4025	0.4634	0.6929	0.025*
C9	0.2289 (2)	0.45255 (11)	0.5313 (2)	0.0185 (4)
H9A	0.1501	0.4854	0.5017	0.022*
C10	0.1895 (2)	0.37290 (11)	0.5803 (2)	0.0169 (4)
C11	0.0934 (2)	0.36814 (11)	0.6637 (2)	0.0197 (5)
C12	0.0477 (2)	0.29603 (11)	0.7021 (2)	0.0188 (5)
H12A	−0.0207	0.2936	0.7552	0.023*
C13	0.1030 (2)	0.22825 (11)	0.6622 (2)	0.0169 (4)
C14	0.2058 (2)	0.23196 (11)	0.5876 (2)	0.0159 (4)
C15	0.2472 (2)	0.30401 (11)	0.5455 (2)	0.0173 (4)
H15A	0.3156	0.3065	0.4925	0.021*
C16	−0.0213 (3)	0.43603 (13)	0.8271 (3)	0.0270 (5)
H16A	−0.0456	0.4892	0.8499	0.041*
H16B	0.0349	0.4139	0.9221	0.041*
H16C	−0.0983	0.4038	0.7961	0.041*
C17	−0.0519 (2)	0.14953 (12)	0.7498 (3)	0.0246 (5)
H17A	−0.0727	0.0946	0.7626	0.037*
H17B	−0.1220	0.1743	0.6732	0.037*
H17C	−0.0399	0.1762	0.8523	0.037*
C18	0.3688 (2)	0.16518 (12)	0.4928 (3)	0.0213 (5)
H18A	0.4007	0.1123	0.4825	0.032*
H18B	0.4357	0.1962	0.5615	0.032*
H18C	0.3450	0.1895	0.3877	0.032*
H1N1	0.241 (3)	0.4165 (16)	0.317 (3)	0.037 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0502 (13)	0.0223 (8)	0.0222 (8)	−0.0092 (8)	0.0077 (8)	−0.0045 (6)
O2	0.0385 (11)	0.0150 (7)	0.0295 (9)	0.0050 (7)	0.0196 (8)	0.0012 (6)
O3	0.0240 (9)	0.0132 (7)	0.0206 (7)	−0.0036 (6)	0.0093 (7)	0.0000 (6)
O4	0.0218 (9)	0.0126 (7)	0.0237 (8)	0.0007 (6)	0.0077 (7)	0.0000 (6)
N1	0.0262 (11)	0.0151 (8)	0.0161 (9)	−0.0046 (7)	0.0070 (8)	−0.0002 (7)
C1	0.0160 (11)	0.0151 (9)	0.0205 (10)	0.0004 (8)	0.0062 (9)	0.0006 (8)
C2	0.0206 (12)	0.0191 (10)	0.0222 (11)	−0.0015 (8)	0.0088 (9)	−0.0025 (8)
C3	0.0228 (13)	0.0263 (11)	0.0213 (11)	−0.0021 (9)	0.0094 (10)	0.0012 (9)
C4	0.0332 (15)	0.0187 (10)	0.0289 (12)	−0.0064 (10)	0.0124 (11)	0.0016 (9)
C5	0.0318 (15)	0.0188 (10)	0.0270 (12)	−0.0078 (9)	0.0101 (11)	−0.0022 (9)
C6	0.0213 (12)	0.0169 (10)	0.0201 (10)	−0.0030 (8)	0.0055 (9)	−0.0007 (8)
C7	0.0230 (13)	0.0193 (10)	0.0212 (11)	−0.0037 (9)	0.0059 (9)	−0.0008 (8)
C8	0.0276 (13)	0.0180 (10)	0.0158 (10)	−0.0007 (9)	0.0040 (9)	0.0006 (8)
C9	0.0234 (13)	0.0145 (9)	0.0187 (10)	0.0005 (8)	0.0070 (9)	0.0012 (7)
C10	0.0214 (12)	0.0134 (9)	0.0160 (9)	−0.0009 (8)	0.0043 (9)	0.0006 (7)
C11	0.0266 (13)	0.0141 (9)	0.0184 (10)	0.0009 (8)	0.0051 (9)	−0.0009 (8)
C12	0.0223 (13)	0.0181 (10)	0.0174 (10)	0.0010 (8)	0.0077 (9)	0.0017 (8)
C13	0.0235 (12)	0.0134 (9)	0.0129 (9)	−0.0023 (8)	0.0018 (8)	0.0014 (7)
C14	0.0212 (12)	0.0129 (9)	0.0128 (9)	0.0012 (8)	0.0019 (8)	−0.0013 (7)
C15	0.0194 (12)	0.0164 (9)	0.0165 (10)	−0.0004 (8)	0.0044 (9)	0.0016 (8)
C16	0.0357 (15)	0.0231 (11)	0.0262 (12)	0.0103 (10)	0.0154 (11)	0.0034 (9)
C17	0.0275 (14)	0.0198 (11)	0.0294 (12)	−0.0029 (9)	0.0125 (10)	0.0019 (9)
C18	0.0224 (13)	0.0192 (10)	0.0250 (11)	0.0013 (9)	0.0111 (10)	0.0000 (8)

O1—C7	1.224 (2)	C8—C9	1.519 (3)
O2—C11	1.377 (2)	C8—H8A	0.9900
O2—C16	1.417 (3)	C8—H8B	0.9900
O3—C13	1.379 (2)	C9—C10	1.518 (3)
O3—C17	1.432 (3)	C9—H9A	1.0000
O4—C14	1.377 (2)	C10—C11	1.387 (3)
O4—C18	1.435 (3)	C10—C15	1.398 (3)
N1—C1	1.383 (3)	C11—C12	1.398 (3)
N1—C9	1.470 (3)	C12—C13	1.384 (3)
N1—H1N1	0.90 (3)	C12—H12A	0.9500
C1—C2	1.407 (3)	C13—C14	1.400 (3)
C1—C6	1.409 (3)	C14—C15	1.389 (3)
C2—C3	1.380 (3)	C15—H15A	0.9500
C2—H2A	0.9500	C16—H16A	0.9800
C3—C4	1.401 (3)	C16—H16B	0.9800
C3—H3A	0.9500	C16—H16C	0.9800
C4—C5	1.379 (3)	C17—H17A	0.9800
C4—H4A	0.9500	C17—H17B	0.9800
C5—C6	1.405 (3)	C17—H17C	0.9800
C5—H5A	0.9500	C18—H18A	0.9800
C6—C7	1.482 (3)	C18—H18B	0.9800
C7—C8	1.511 (3)	C18—H18C	0.9800
C11—O2—C16	116.60 (16)	C8—C9—H9A	107.9
C13—O3—C17	116.79 (16)	C11—C10—C15	118.63 (18)
C14—O4—C18	116.03 (15)	C11—C10—C9	118.94 (18)
C1—N1—C9	115.41 (16)	C15—C10—C9	122.42 (19)
C1—N1—H1N1	115.3 (16)	O2—C11—C10	116.43 (18)
C9—N1—H1N1	111.6 (17)	O2—C11—C12	122.38 (19)
N1—C1—C2	120.58 (18)	C10—C11—C12	121.16 (19)
N1—C1—C6	120.86 (18)	C13—C12—C11	119.4 (2)
C2—C1—C6	118.56 (18)	C13—C12—H12A	120.3
C3—C2—C1	120.75 (19)	C11—C12—H12A	120.3
C3—C2—H2A	119.6	O3—C13—C12	123.56 (19)
C1—C2—H2A	119.6	O3—C13—C14	116.19 (18)
C2—C3—C4	120.83 (19)	C12—C13—C14	120.25 (18)
C2—C3—H3A	119.6	O4—C14—C15	124.66 (19)
C4—C3—H3A	119.6	O4—C14—C13	115.80 (17)
C5—C4—C3	118.9 (2)	C15—C14—C13	119.53 (18)
C5—C4—H4A	120.5	C14—C15—C10	120.82 (19)
C3—C4—H4A	120.5	C14—C15—H15A	119.6
C4—C5—C6	121.3 (2)	C10—C15—H15A	119.6
C4—C5—H5A	119.3	O2—C16—H16A	109.5
C6—C5—H5A	119.3	O2—C16—H16B	109.5
C5—C6—C1	119.58 (19)	H16A—C16—H16B	109.5
C5—C6—C7	120.06 (19)	O2—C16—H16C	109.5
C1—C6—C7	120.37 (18)	H16A—C16—H16C	109.5
O1—C7—C6	122.93 (19)	H16B—C16—H16C	109.5
O1—C7—C8	121.87 (18)	O3—C17—H17A	109.5
C6—C7—C8	115.19 (17)	O3—C17—H17B	109.5
C7—C8—C9	110.81 (17)	H17A—C17—H17B	109.5
C7—C8—H8A	109.5	O3—C17—H17C	109.5
C9—C8—H8A	109.5	H17A—C17—H17C	109.5
C7—C8—H8B	109.5	H17B—C17—H17C	109.5
C9—C8—H8B	109.5	O4—C18—H18A	109.5
H8A—C8—H8B	108.1	O4—C18—H18B	109.5
N1—C9—C10	112.03 (16)	H18A—C18—H18B	109.5
N1—C9—C8	108.16 (18)	O4—C18—H18C	109.5
C10—C9—C8	112.88 (17)	H18A—C18—H18C	109.5
N1—C9—H9A	107.9	H18B—C18—H18C	109.5
C10—C9—H9A	107.9
C9—N1—C1—C2	−153.9 (2)	N1—C9—C10—C15	25.1 (3)
C9—N1—C1—C6	25.2 (3)	C8—C9—C10—C15	−97.3 (2)
N1—C1—C2—C3	176.4 (2)	C16—O2—C11—C10	−160.0 (2)
C6—C1—C2—C3	−2.7 (3)	C16—O2—C11—C12	21.9 (3)
C1—C2—C3—C4	1.0 (4)	C15—C10—C11—O2	177.03 (19)
C2—C3—C4—C5	1.0 (4)	C9—C10—C11—O2	−2.5 (3)
C3—C4—C5—C6	−1.2 (4)	C15—C10—C11—C12	−4.8 (3)
C4—C5—C6—C1	−0.5 (4)	C9—C10—C11—C12	175.6 (2)
C4—C5—C6—C7	179.3 (2)	O2—C11—C12—C13	−179.2 (2)
N1—C1—C6—C5	−176.7 (2)	C10—C11—C12—C13	2.8 (3)
C2—C1—C6—C5	2.5 (3)	C17—O3—C13—C12	8.6 (3)
N1—C1—C6—C7	3.5 (3)	C17—O3—C13—C14	−171.93 (18)
C2—C1—C6—C7	−177.4 (2)	C11—C12—C13—O3	−179.02 (19)
C5—C6—C7—O1	0.5 (4)	C11—C12—C13—C14	1.6 (3)
C1—C6—C7—O1	−179.7 (2)	C18—O4—C14—C15	3.5 (3)
C5—C6—C7—C8	−178.2 (2)	C18—O4—C14—C13	−176.60 (18)
C1—C6—C7—C8	1.6 (3)	O3—C13—C14—O4	−3.1 (3)
O1—C7—C8—C9	148.3 (2)	C12—C13—C14—O4	176.39 (19)
C6—C7—C8—C9	−33.0 (3)	O3—C13—C14—C15	176.84 (18)
C1—N1—C9—C10	178.76 (19)	C12—C13—C14—C15	−3.7 (3)
C1—N1—C9—C8	−56.2 (2)	O4—C14—C15—C10	−178.52 (19)
C7—C8—C9—N1	59.1 (2)	C13—C14—C15—C10	1.6 (3)
C7—C8—C9—C10	−176.39 (18)	C11—C10—C15—C14	2.6 (3)
N1—C9—C10—C11	−155.4 (2)	C9—C10—C15—C14	−177.8 (2)
C8—C9—C10—C11	82.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O3i	0.90 (3)	2.32 (3)	3.156 (2)	155 (3)
C2—H2A···O4i	0.95	2.59	3.439 (3)	150
C16—H16B···O3ii	0.98	2.58	3.459 (3)	150
C8—H8B···Cg1iii	0.99	2.74	3.698 (2)	164
C16—H16C···Cg1iv	0.98	2.68	3.518 (3)	144
C17—H17C···Cg2ii	0.98	2.76	3.560 (3)	140
C18—H18C···Cg2i	0.98	2.75	3.574 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O3i	0.90 (3)	2.32 (3)	3.156 (2)	155 (3)
C2—H2A⋯O4i	0.95	2.59	3.439 (3)	150
C16—H16B⋯O3ii	0.98	2.58	3.459 (3)	150
C8—H8B⋯Cg1iii	0.99	2.74	3.698 (2)	164
C16—H16C⋯Cg1iv	0.98	2.68	3.518 (3)	144
C17—H17C⋯Cg2ii	0.98	2.76	3.560 (3)	140
C18—H18C⋯Cg2i	0.98	2.75	3.574 (3)	142

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