4-(3,4-Dimethyl-5-phenyl-1,3-oxazolidin-2-yl)-2-methoxy­phenol

Asaruddin, M.R.; Wahab, H.A.; Mohamed, N.; Goh, J.H.; Fun, H.-K.

doi:10.1107/S1600536810018891

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 6| June 2010| Pages o1452-o1453

https://doi.org/10.1107/S1600536810018891

Open

access

4-(3,4-Dimethyl-5-phenyl-1,3-oxazolidin-2-yl)-2-methoxyphenol

Mohd Razip Asaruddin,^a Habibah A Wahab,^b ‡ Nornisah Mohamed,^a Jia Hao Goh ^c § and Hoong-Kun Fun ^c ^*¶

^aPharmaceutical Design and Simulation Laboratory, School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bInstitute of Pharmaceutical and Neutraceuticals, Malaysia Ministry of Science and Technology and Innovation, Science Complex, 11900, Penang, Malaysia, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 17 May 2010; accepted 20 May 2010; online 26 May 2010)

In the title compound, C₁₈H₂₁NO₃, the oxazolidine ring adopts an envelope conformation with the N atom at the flap position. The two benzene rings make dihedral angles of 74.27 (14) and 73.26 (15)° with the mean plane through the oxazolidine ring. In the crystal structure, O—H⋯O and C—H⋯O hydrogen bonds connect adjacent molecules into chains along [010] incorporating R₂²(8) loops and further stabilization is provided by weak intermolecular C—H⋯π interactions.

Related literature

For general background to and applications of the title oxazolidine compound, see: Fitzgerald et al. (2005 ); Kamat et al. (2000 ); Kumar et al. (2004 ); Walton et al. (2003 ). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995 ). For a related structure, see: Duffy et al. (2004 ). For bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₈H₂₁NO₃
M_r = 299.36
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.8893 (6) Å
b = 11.7697 (9) Å
c = 17.4392 (13) Å
V = 1619.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 120 K
0.31 × 0.15 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.975, T_max = 0.987
9140 measured reflections
2131 independent reflections
1622 reflections with I > 2σ(I)
R_int = 0.067

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.096
S = 1.07
2131 reflections
206 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10–C15 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O3ⁱ	0.92 (4)	2.08 (3)	2.909 (3)	148 (3)
C5—H5A⋯O1ⁱⁱ	0.93	2.42	3.244 (3)	148
C16—H16A⋯Cg1ⁱⁱⁱ	0.96	2.91	3.628 (3)	133
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, -y-1, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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: https://doi.org/10.1107/S1600536810018891/hb5455sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810018891/hb5455Isup2.hkl

checkCIF report

Comment top

4-Hydroxy-3-methoxybenzyldehyde has been used as a chemical intermediate in the production of pharmaceuticals and other chemicals. This compound is a widely used flavouring compound in food and personal products. The synthesis of new design chemical entity is part of the aim to produce pharmaceutical substances because the compound in the literature shown remarkable biological activities, such as anti-oxidant and anti-microbial properties (Fitzgerald et al., 2005; Kamat et al., 2000; Walton et al., 2003; Kumar et al., 2004). In this paper we report the full account of the structural data of the title oxazolidine compound, (I).

The title oxazolidine compound contains two aromatic phenyl rings bridged by an oxazolidine ring (Fig. 1). The oxazolidine ring with atom sequence C7/N1/C8/C9/O3 adopts an envolope conformation, with puckering parameters of Q = 0.421 (3) Å and φ = 73.7 (3)°. The N1 atom is at the envelope flap position and it deviates from the least-square plane through the remaining four atoms by 0.634 (2) Å. The mean plane through the oxazolidine ring inclines at dihedral angles of 74.27 (14) and 73.26 (15)°, respectively, with the C1-C6 and C10-C15 phenyl rings. The bond lengths (Allen et al., 1987) and angles are within normal ranges and consistent to a closely related oxazolidine structure (Duffy et al., 2004).

In the crystal structure (Fig. 2), adjacent molecules are connected by intermolecular O1—H1O1···O3 and C5—H5A···O1 hydrogen bonds (Table 1) into one-dimensional chains along the [010] direction incorporating R²₂(8) hydrogen bond ring motifs (Bernstein et al., 1995). The crystal structure is further stabilized by weak intermolecular C16—H16A···Cg1 interactions (Table 1) involving the centroid of the C10-C15 phenyl ring.

Related literature top

For general background to and applications of the title oxazolidine compound, see: Fitzgerald et al. (2005); Kamat et al. (2000); Kumar et al. (2004); Walton et al. (2003). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995). For a related structure, see: Duffy et al. (2004). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

An anhydrous methanol solution of 4-hydroxy-3-methoxy-benzyldehyde (1.52 g, 10 mmol) was added to an anhydrous methanol solution of 2-methylamino-1-phenylpropan-1-ol (1.65 g, 10 mmol) and the reaction mixture was refluxed and stirred at 350 K for 8 h. The product was isolated and recrystallized from methanol and dried in vacuo to give colourless blocks of (I) in 80 % yield, which were washed three times with ethyl acetate and dried in a vacuum desiccator using CaCl₂.

Structure description top

For general background to and applications of the title oxazolidine compound, see: Fitzgerald et al. (2005); Kamat et al. (2000); Kumar et al. (2004); Walton et al. (2003). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995). For a related structure, see: Duffy et al. (2004). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 (I) showing 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal structure of (I), viewed along the a axis, showing one-dimensional chains along the [010] direction. Hydrogen atoms not involved in intermolecular interactions (dashed lines) have been omitted for clarity.

4-(3,4-Dimethyl-5-phenyl-1,3-oxazolidin-2-yl)-2-methoxyphenol top

Crystal data top

C₁₈H₂₁NO₃	F(000) = 640
M_r = 299.36	D_x = 1.228 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2249 reflections
a = 7.8893 (6) Å	θ = 2.3–30.0°
b = 11.7697 (9) Å	µ = 0.08 mm⁻¹
c = 17.4392 (13) Å	T = 120 K
V = 1619.3 (2) Å³	Block, colourless
Z = 4	0.31 × 0.15 × 0.15 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	2131 independent reflections
Radiation source: fine-focus sealed tube	1622 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.067
φ and ω scans	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
T_min = 0.975, T_max = 0.987	k = −15→12
9140 measured reflections	l = −22→20

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0389P)² + 0.1539P] where P = (F_o² + 2F_c²)/3
2131 reflections	(Δ/σ)_max < 0.001
206 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₈H₂₁NO₃	V = 1619.3 (2) Å³
M_r = 299.36	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.8893 (6) Å	µ = 0.08 mm⁻¹
b = 11.7697 (9) Å	T = 120 K
c = 17.4392 (13) Å	0.31 × 0.15 × 0.15 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	2131 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1622 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.987	R_int = 0.067
9140 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.19 e Å⁻³
2131 reflections	Δρ_min = −0.21 e Å⁻³
206 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 esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.6439 (2)	−0.37357 (17)	0.20663 (13)	0.0265 (5)
O2	0.5613 (2)	−0.21380 (16)	0.30639 (11)	0.0268 (5)
O3	0.2181 (2)	0.07593 (15)	0.14249 (11)	0.0212 (4)
N1	0.0098 (3)	−0.05656 (19)	0.15472 (13)	0.0233 (5)
C1	0.3559 (4)	−0.2052 (2)	0.08866 (16)	0.0253 (7)
H1A	0.3145	−0.2043	0.0387	0.030*
C2	0.4683 (3)	−0.2903 (2)	0.11104 (17)	0.0255 (6)
H2A	0.4999	−0.3467	0.0765	0.031*
C3	0.5324 (3)	−0.2906 (2)	0.18443 (17)	0.0215 (6)
C4	0.4854 (3)	−0.2053 (2)	0.23596 (16)	0.0206 (6)
C5	0.3704 (3)	−0.1229 (2)	0.21429 (16)	0.0207 (6)
H5A	0.3363	−0.0678	0.2493	0.025*
C6	0.3054 (3)	−0.1223 (2)	0.13965 (16)	0.0210 (6)
C7	0.1731 (3)	−0.0363 (2)	0.11753 (16)	0.0203 (6)
H7A	0.1583	−0.0366	0.0617	0.024*
C8	−0.0791 (3)	0.0517 (2)	0.14323 (17)	0.0234 (6)
H8A	−0.1136	0.0585	0.0894	0.028*
C9	0.0619 (3)	0.1373 (2)	0.16032 (15)	0.0217 (6)
H9A	0.0606	0.1547	0.2153	0.026*
C10	0.0490 (3)	0.2465 (2)	0.11626 (16)	0.0204 (6)
C11	−0.0056 (4)	0.3445 (2)	0.15220 (18)	0.0284 (7)
H11A	−0.0288	0.3435	0.2045	0.034*
C12	−0.0263 (4)	0.4449 (3)	0.1110 (2)	0.0365 (8)
H12A	−0.0623	0.5105	0.1358	0.044*
C13	0.0064 (4)	0.4468 (3)	0.0336 (2)	0.0355 (8)
H13A	−0.0090	0.5134	0.0058	0.043*
C14	0.0625 (4)	0.3493 (3)	−0.00306 (18)	0.0328 (7)
H14A	0.0852	0.3504	−0.0554	0.039*
C15	0.0844 (4)	0.2504 (3)	0.03850 (17)	0.0264 (7)
H15A	0.1236	0.1854	0.0139	0.032*
C16	0.5385 (4)	−0.1212 (2)	0.35869 (16)	0.0275 (6)
H16A	0.6074	−0.1333	0.4033	0.041*
H16B	0.4215	−0.1169	0.3736	0.041*
H16C	0.5713	−0.0516	0.3342	0.041*
C17	−0.0798 (4)	−0.1538 (3)	0.12300 (19)	0.0343 (8)
H17A	−0.0103	−0.2204	0.1276	0.051*
H17C	−0.1044	−0.1402	0.0699	0.051*
H17D	−0.1838	−0.1651	0.1506	0.051*
C18	−0.2325 (3)	0.0658 (3)	0.19449 (18)	0.0320 (7)
H18A	−0.3176	0.0114	0.1803	0.048*
H18D	−0.2771	0.1412	0.1888	0.048*
H18B	−0.2001	0.0538	0.2469	0.048*
H1O1	0.658 (4)	−0.368 (3)	0.259 (2)	0.048 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0250 (10)	0.0216 (11)	0.0331 (12)	0.0061 (8)	−0.0054 (9)	−0.0006 (10)
O2	0.0282 (10)	0.0223 (10)	0.0299 (11)	0.0039 (8)	−0.0080 (9)	−0.0025 (9)
O3	0.0145 (8)	0.0178 (9)	0.0314 (11)	0.0008 (7)	−0.0010 (8)	−0.0004 (9)
N1	0.0171 (10)	0.0220 (12)	0.0309 (13)	−0.0005 (10)	0.0003 (10)	0.0015 (11)
C1	0.0255 (14)	0.0259 (15)	0.0246 (16)	−0.0010 (13)	0.0001 (13)	0.0009 (14)
C2	0.0257 (15)	0.0193 (14)	0.0316 (16)	0.0008 (12)	0.0024 (13)	−0.0037 (13)
C3	0.0163 (13)	0.0167 (13)	0.0316 (16)	−0.0010 (11)	−0.0015 (12)	0.0033 (13)
C4	0.0170 (13)	0.0195 (13)	0.0252 (15)	−0.0042 (11)	−0.0015 (11)	0.0011 (13)
C5	0.0178 (12)	0.0160 (14)	0.0283 (15)	−0.0010 (11)	0.0025 (11)	−0.0022 (13)
C6	0.0188 (13)	0.0188 (14)	0.0255 (15)	−0.0039 (11)	0.0013 (12)	0.0027 (13)
C7	0.0190 (13)	0.0176 (14)	0.0243 (15)	−0.0006 (11)	−0.0014 (11)	0.0003 (12)
C8	0.0180 (12)	0.0246 (15)	0.0274 (15)	−0.0004 (12)	−0.0017 (12)	0.0051 (13)
C9	0.0179 (12)	0.0240 (14)	0.0233 (15)	0.0037 (12)	0.0014 (12)	0.0006 (13)
C10	0.0110 (12)	0.0238 (15)	0.0263 (15)	0.0001 (11)	−0.0047 (11)	−0.0001 (12)
C11	0.0229 (14)	0.0284 (16)	0.0339 (17)	0.0034 (13)	0.0024 (13)	−0.0019 (14)
C12	0.0288 (17)	0.0238 (17)	0.057 (2)	0.0078 (14)	−0.0003 (16)	−0.0010 (16)
C13	0.0293 (15)	0.0245 (17)	0.053 (2)	0.0011 (15)	−0.0081 (16)	0.0161 (16)
C14	0.0293 (16)	0.0375 (19)	0.0315 (17)	−0.0066 (15)	−0.0048 (14)	0.0086 (15)
C15	0.0249 (14)	0.0245 (15)	0.0298 (16)	−0.0007 (13)	−0.0014 (13)	0.0012 (13)
C16	0.0293 (15)	0.0271 (15)	0.0259 (15)	0.0059 (13)	−0.0032 (13)	−0.0018 (14)
C17	0.0235 (14)	0.0289 (17)	0.050 (2)	−0.0086 (13)	0.0014 (15)	0.0005 (16)
C18	0.0220 (14)	0.0352 (17)	0.0389 (18)	0.0019 (13)	0.0051 (14)	0.0042 (16)

Geometric parameters (Å, º) top

O1—C3	1.370 (3)	C9—C10	1.501 (4)
O1—H1O1	0.92 (3)	C9—H9A	0.9800
O2—C4	1.370 (3)	C10—C11	1.382 (4)
O2—C16	1.432 (3)	C10—C15	1.385 (4)
O3—C7	1.435 (3)	C11—C12	1.393 (4)
O3—C9	1.462 (3)	C11—H11A	0.9300
N1—C17	1.455 (4)	C12—C13	1.374 (5)
N1—C7	1.462 (3)	C12—H12A	0.9300
N1—C8	1.468 (3)	C13—C14	1.386 (4)
C1—C6	1.379 (4)	C13—H13A	0.9300
C1—C2	1.394 (4)	C14—C15	1.382 (4)
C1—H1A	0.9300	C14—H14A	0.9300
C2—C3	1.376 (4)	C15—H15A	0.9300
C2—H2A	0.9300	C16—H16A	0.9600
C3—C4	1.397 (4)	C16—H16B	0.9600
C4—C5	1.381 (4)	C16—H16C	0.9600
C5—C6	1.399 (4)	C17—H17A	0.9600
C5—H5A	0.9300	C17—H17C	0.9600
C6—C7	1.505 (4)	C17—H17D	0.9600
C7—H7A	0.9800	C18—H18A	0.9600
C8—C18	1.514 (4)	C18—H18D	0.9600
C8—C9	1.530 (4)	C18—H18B	0.9600
C8—H8A	0.9800

C3—O1—H1O1	108 (2)	O3—C9—H9A	108.7
C4—O2—C16	117.4 (2)	C10—C9—H9A	108.7
C7—O3—C9	108.10 (19)	C8—C9—H9A	108.7
C17—N1—C7	112.8 (2)	C11—C10—C15	118.6 (3)
C17—N1—C8	113.5 (2)	C11—C10—C9	120.3 (3)
C7—N1—C8	102.6 (2)	C15—C10—C9	121.0 (2)
C6—C1—C2	120.8 (3)	C10—C11—C12	120.7 (3)
C6—C1—H1A	119.6	C10—C11—H11A	119.7
C2—C1—H1A	119.6	C12—C11—H11A	119.7
C3—C2—C1	119.7 (3)	C13—C12—C11	119.9 (3)
C3—C2—H2A	120.1	C13—C12—H12A	120.0
C1—C2—H2A	120.1	C11—C12—H12A	120.0
O1—C3—C2	120.0 (3)	C12—C13—C14	120.0 (3)
O1—C3—C4	120.0 (2)	C12—C13—H13A	120.0
C2—C3—C4	119.9 (2)	C14—C13—H13A	120.0
O2—C4—C5	125.7 (2)	C15—C14—C13	119.7 (3)
O2—C4—C3	114.1 (2)	C15—C14—H14A	120.1
C5—C4—C3	120.2 (2)	C13—C14—H14A	120.1
C4—C5—C6	119.9 (3)	C14—C15—C10	121.0 (3)
C4—C5—H5A	120.0	C14—C15—H15A	119.5
C6—C5—H5A	120.0	C10—C15—H15A	119.5
C1—C6—C5	119.4 (2)	O2—C16—H16A	109.5
C1—C6—C7	120.8 (3)	O2—C16—H16B	109.5
C5—C6—C7	119.8 (2)	H16A—C16—H16B	109.5
O3—C7—N1	103.5 (2)	O2—C16—H16C	109.5
O3—C7—C6	111.7 (2)	H16A—C16—H16C	109.5
N1—C7—C6	112.8 (2)	H16B—C16—H16C	109.5
O3—C7—H7A	109.5	N1—C17—H17A	109.5
N1—C7—H7A	109.5	N1—C17—H17C	109.5
C6—C7—H7A	109.5	H17A—C17—H17C	109.5
N1—C8—C18	113.4 (2)	N1—C17—H17D	109.5
N1—C8—C9	101.4 (2)	H17A—C17—H17D	109.5
C18—C8—C9	113.2 (2)	H17C—C17—H17D	109.5
N1—C8—H8A	109.5	C8—C18—H18A	109.5
C18—C8—H8A	109.5	C8—C18—H18D	109.5
C9—C8—H8A	109.5	H18A—C18—H18D	109.5
O3—C9—C10	111.8 (2)	C8—C18—H18B	109.5
O3—C9—C8	104.25 (19)	H18A—C18—H18B	109.5
C10—C9—C8	114.5 (2)	H18D—C18—H18B	109.5

C6—C1—C2—C3	−1.3 (4)	C5—C6—C7—N1	−69.3 (3)
C1—C2—C3—O1	−179.5 (2)	C17—N1—C8—C18	73.7 (3)
C1—C2—C3—C4	−0.4 (4)	C7—N1—C8—C18	−164.2 (2)
C16—O2—C4—C5	−9.2 (4)	C17—N1—C8—C9	−164.6 (2)
C16—O2—C4—C3	171.4 (2)	C7—N1—C8—C9	−42.5 (2)
O1—C3—C4—O2	0.7 (3)	C7—O3—C9—C10	−124.5 (2)
C2—C3—C4—O2	−178.4 (2)	C7—O3—C9—C8	−0.3 (3)
O1—C3—C4—C5	−178.7 (2)	N1—C8—C9—O3	26.4 (2)
C2—C3—C4—C5	2.2 (4)	C18—C8—C9—O3	148.2 (2)
O2—C4—C5—C6	178.4 (2)	N1—C8—C9—C10	148.9 (2)
C3—C4—C5—C6	−2.3 (4)	C18—C8—C9—C10	−89.3 (3)
C2—C1—C6—C5	1.2 (4)	O3—C9—C10—C11	−136.8 (2)
C2—C1—C6—C7	−174.8 (2)	C8—C9—C10—C11	104.9 (3)
C4—C5—C6—C1	0.6 (4)	O3—C9—C10—C15	45.9 (3)
C4—C5—C6—C7	176.7 (2)	C8—C9—C10—C15	−72.4 (3)
C9—O3—C7—N1	−26.2 (2)	C15—C10—C11—C12	0.7 (4)
C9—O3—C7—C6	−147.9 (2)	C9—C10—C11—C12	−176.7 (3)
C17—N1—C7—O3	165.9 (2)	C10—C11—C12—C13	0.5 (4)
C8—N1—C7—O3	43.3 (2)	C11—C12—C13—C14	−1.0 (5)
C17—N1—C7—C6	−73.2 (3)	C12—C13—C14—C15	0.3 (5)
C8—N1—C7—C6	164.3 (2)	C13—C14—C15—C10	0.9 (4)
C1—C6—C7—O3	−137.2 (3)	C11—C10—C15—C14	−1.4 (4)
C5—C6—C7—O3	46.8 (3)	C9—C10—C15—C14	176.0 (3)
C1—C6—C7—N1	106.7 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C10–C15 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O3ⁱ	0.92 (4)	2.08 (3)	2.909 (3)	148 (3)
C5—H5A···O1ⁱⁱ	0.93	2.42	3.244 (3)	148
C16—H16A···Cg1ⁱⁱⁱ	0.96	2.91	3.628 (3)	133

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+3/2, −y−1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₁NO₃
M_r	299.36
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	120
a, b, c (Å)	7.8893 (6), 11.7697 (9), 17.4392 (13)
V (Å³)	1619.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.31 × 0.15 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.975, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	9140, 2131, 1622
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.096, 1.07
No. of reflections	2131
No. of parameters	206
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.21

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C10–C15 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O3ⁱ	0.92 (4)	2.08 (3)	2.909 (3)	148 (3)
C5—H5A···O1ⁱⁱ	0.93	2.42	3.244 (3)	148
C16—H16A···Cg1ⁱⁱⁱ	0.96	2.91	3.628 (3)	133

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+3/2, −y−1, z+1/2.

Footnotes

‡Additional correspondence author, e-mail: habibahw@usm.my, habibah@ipharm.gov.my. On secondment from: Pharmaceutical Design and Simulation Laboratory, School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia.

§Thomson Reuters ResearcherID: C-7576-2009.

¶Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

This research was supported by Universiti Sains Malaysia (USM) under the University Research grant (No. 1001/PFARMASI/815004) and the Ministry of Science, Technology and Innovation through R&D Initiative Grant (311/IFN/692601). HKF and JHG thank USM for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). MRA gratefully acknowledges a PhD scholarship from Universiti Malaysia Sarawak. JHG also thanks USM for the award of a USM fellowship.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Duffy, M., Gallagher, J. F. & Lough, A. J. (2004). Acta Cryst. E60, o234–o236. Web of Science CSD CrossRef IUCr Journals Google Scholar
Fitzgerald, D. J., Stratford, M., Gasson, M. J. & Narbad, A. (2005). J. Agric. Food Chem. 53, 1769–1775. Web of Science CrossRef PubMed CAS Google Scholar
Kamat, J. P., Ghosh, A. & Devasagayam, T. P. (2000). Mol. Cell Biochem. 209, 47–53. Web of Science CrossRef PubMed CAS Google Scholar
Kumar, S. S., Priyadarsini, K. I. & Sainis, K. B. (2004). J. Agric. Food Chem. 53, 139–145. Web of Science CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Walton, N. J., Mayer, M. J. & Narbad, A. (2003). Phytochemistry, 63, 505–515. Web of Science CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 6| June 2010| Pages o1452-o1453

https://doi.org/10.1107/S1600536810018891

Open

access