2-(2,4,5-Trimeth­oxy­phen­yl)-2,3-dihydro­quinolin-4(1H)-one

Chantrapromma, S.; Ruanwas, P.; Boonnak, N.; Chantrapromma, K.; Fun, H.-K.

doi:10.1107/S1600536812002917

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o664-o665

doi:10.1107/S1600536812002917

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2-(2,4,5-Trimethoxyphenyl)-2,3-dihydroquinolin-4(1H)-one

Suchada Chantrapromma,^a ^*‡ Pumsak Ruanwas,^a Nawong Boonnak,^a Kan Chantrapromma ^b and Hoong-Kun Fun ^c §

^aCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, ^bResearch Unit of Natural Products Utilization, Walailak University, Thasala, Nakhon Si Thammarat 80160, Thailand, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: suchada.c@psu.ac.th

(Received 10 January 2012; accepted 23 January 2012; online 10 February 2012)

In the title aza-flavanone, C₁₈H₁₉NO₄, an intramolecular 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 methoxy 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 methoxy group at the meta position is almost coplanar [C—O—C—C = 3.5 (3)°]. In the crystal, molecules are linked by N—H⋯O hydrogen bonds and weak C—H⋯O interactions into chains along the [001] direction. Weak C—H⋯π interactions 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_r = 313.34
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.063
wR(F²) = 0.156
S = 1.03
4511 reflections
215 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.30 e Å⁻³

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⋯Cg1^iv	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) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z+1; (iv) -x, -y+1, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812002917/hb6602sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812002917/hb6602Isup3.cml

checkCIF report

Comment top

Aza-flavanone or 2-aryl-2,3-dihydroquinolin-4(1H)-one, a synthesized analogue of flavanone, can be achieved by intramolecular cyclization of a chalcone derivative in basic medium (Xia et al., 1998). They are also found to exhibit antibacterial, antifungal (Göker et al., 2005) and anticancer activities (Xia et al., 1998). In the course of our research on medicinal chemistry, we have synthesized the title aza-flavanone (I) in order to study its biological activity.

The total molecule of (I) is twisted (Fig. 1). The dihedral angle between two benzene rings is 51.03 (10)°. The N-atom containing central ring is in an envelope conformation with the puckered C9 atom having the maximum deviation of 0.352 (2) Å, and the puckering parameter Q = 0.502 (2) Å, θ = 124.5 (2)° and ϕ = 110.8 (3)° (Cremer & Pople, 1975). The three methoxy groups of the 2,4,5-trimethoxyphenyl unit have two different orientations: the two methoxy groups at ortho (at atom C11) and para (at atom C13) positions are slightly twisted from the attached benzene ring with torsion angles C16—O2—C11—C12 = 21.9 (3)° and C17—O3—C13—C14 = -171.93 (18)°, whereas the third one at meta (at atom C14) position is co-planar with the torsion angle of C18—O4—C14—C15 = 3.5 (3)°. These angle values also indicated that the methyl group at para position points towards the ortho-methoxy but points away from the meta-methoxy due to the steric effect.

In the crystal (Fig. 2), the molecules are linked by N—H···O hydrogen bonds and weak C—H···O interactions (Table 1) into chains along the c axis. C—H···π interactions (Table 1) also occur.

Related literature top

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 top

To a 50 ml round-bottom flask filled with 2,4,5-trimethoxybenzaldehyde (0.50 g, 2.55 mmol), EtOH (20 ml) and 2-aminoacetophenone (0.31 ml, 2.55 mmol) were sequentially added at room temperature. After stirring for a while, 5 ml of 30% NaOH (aq) was added slowly and was then further stirred for 2 h. A pale yellow precipitate was formed and collected by filtration yielding the title compound (I) (1.26 g, 75% yield), which was further recrystallized in EtOH to obtain yellow needles of (I) after several days, m.p. 419–420 K.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids.
	Fig. 2. Partial packing diagram of the title compound viewed approximately along the b axis, showing chains running along the c axis. Hydrogen bonds are shown as dashed lines.

2-(2,4,5-Trimethoxyphenyl)-2,3-dihydroquinolin-4(1H)-one top

Crystal data top

C₁₈H₁₉NO₄	F(000) = 664
M_r = 313.34	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0535P)² + 0.8134P] where P = (F_o² + 2F_c²)/3
4511 reflections	(Δ/σ)_max = 0.001
215 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₈H₁₉NO₄	V = 1551.6 (3) Å³
M_r = 313.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.7354 (11) Å	µ = 0.10 mm⁻¹
b = 17.1525 (16) Å	T = 100 K
c = 8.6471 (8) Å	0.41 × 0.16 × 0.06 mm
β = 102.981 (2)°

Data collection top

Bruker APEXII CCD diffractometer	4511 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2751 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.994	R_int = 0.062
13335 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.38 e Å⁻³
4511 reflections	Δρ_min = −0.30 e Å⁻³
215 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···Cg1^iv	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) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2; (iii) −x+1, −y+1, −z+1; (iv) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₉NO₄
M_r	313.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.7354 (11), 17.1525 (16), 8.6471 (8)
β (°)	102.981 (2)
V (Å³)	1551.6 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.41 × 0.16 × 0.06

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.962, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	13335, 4511, 2751
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.156, 1.03
No. of reflections	4511
No. of parameters	215
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.30

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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···Cg1^iv	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) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2; (iii) −x+1, −y+1, −z+1; (iv) −x, −y+1, −z+1.

Footnotes

‡Thomson Reuters ResearcherID: A-5085-2009.

§Visiting Professor, College of Pharmacy, King Saud University, Riyadh, Saudi Arabia. Additional correspondence author, email: hkfun@usm.my. Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank the Prince of Songkla University and the Universiti Sains Malaysia for Research University grant No. 1001/PFIZIK/811160. PR thanks the Crystal Materials Research Unit, Prince of Songkla University, for financial support. NW thanks the Prince of Songkla University for a postdoctoral fellowship. HKF thanks King Saud University, Riyadh, Saudi Arabia, for the award of a visiting professorship (23 December 2011 to 14 January 2012).

References

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Volume 68| Part 3| March 2012| Pages o664-o665

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