2-Bromo-4-(3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-yl)-6-meth­oxy­phenol

Hariono, M.; Ngah, N.; Wahab, H.A.; Abdul Rahim, A.S.

doi:10.1107/S1600536811051269

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 1| January 2012| Pages o35-o36

doi:10.1107/S1600536811051269

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2-Bromo-4-(3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-yl)-6-methoxyphenol

Maywan Hariono,^a Nurziana Ngah,^b Habibah A. Wahab ^a and Aisyah Saad Abdul Rahim ^a ^*

^aSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM Penang, Malaysia, and ^bKulliyyah of Science, International Islamic University Malaysia, Bandar Indera Mahkota, 25200 Kuantan, Pahang, Malaysia
^*Correspondence e-mail: aisyah@usm.my

(Received 24 November 2011; accepted 29 November 2011; online 7 December 2011)

In the title compound, C₁₈H₂₀BrNO₃, the oxazolidine ring adopts an envelope conformation with the N atom at the flap position. The mean plane of oxazolidine ring makes dihedral angles of 82.96 (13) and 70.97 (12)°, respectively, with the phenyl and benzene rings. In the crystal, adjacent molecules are connected via O—H⋯O and C—H⋯O hydrogen bonds and C—H⋯π interactions into a zigzag chain along the b axis.

Related literature

For the synthesis and closely related structures, see: Asaruddin et al. (2010 ); Diwischeck et al. (2003 ); Khruscheva et al. (1997 ); Duffy et al. (2004 ). For therapeutic properties of oxazolidine derivatives, see: Moloney et al. (1998 ); Wang et al. (2010 ); Nakano et al. (2010 ); Fülöp et al. (2004 ); Panneerselvam (2011 ). For standard bond lengths, see: Allen et al. (1987 ). For the low-temperature device used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₈H₂₀BrNO₃
M_r = 378.26
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.8056 (4) Å
b = 11.9034 (6) Å
c = 18.9109 (9) Å
V = 1757.07 (15) Å³
Z = 4
Mo Kα radiation
μ = 2.35 mm⁻¹
T = 100 K
0.50 × 0.36 × 0.23 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.383, T_max = 0.618
10569 measured reflections
3074 independent reflections
2935 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.056
S = 1.08
3074 reflections
215 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.26 e Å⁻³
Absolute structure: Flack (1983 ), 1283 Friedel pairs
Flack parameter: 0.004 (7)

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.85 (1)	2.03 (1)	2.7853 (19)	148 (2)
C15—H15A⋯O2ⁱⁱ	0.95	2.46	3.232 (3)	138
C18—H18A⋯Cg2ⁱ	0.98	2.96	3.679 (3)	131
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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: 10.1107/S1600536811051269/is5016sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811051269/is5016Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811051269/is5016Isup3.cml

checkCIF report

Comment top

Oxazolidine compounds are important in understanding drug behaviour in medicinal chemistry (Duffy et al., 2004). Derivatives of oxazolidine have shown inhibitory effects for several diseases or condition such as β-adrenoreseptor antagonist (Moloney et al., 1998), influenza antiviral (Wang et al., 2010; Nakano et al., 2010), antinflammatory agents (Fulop et al., 2004) and antihyperglycemic (Panneerselvam, 2011). In this paper, we report the X-ray crystal structure of the title oxazolidine compound, (I).

The title compound, C₁₈H₂₀BrNO₃, consists of two aromatic rings which are connected through oxazolidine ring (Fig. 1). The molecule is similar with those reported by Asaruddin et al. (2010), in that only the present of Br atom at β position of 3-hydroxy-4-methoxyphenyl ring is different. The oxazolidine ring (O1/C7–C9/N1) adopts an envelope conformation with puckering parameters of Q = 0.433 (2) Å and ϕ = 107.3 (3)°. The N1 atom is at the flap position and it deviates from the mean plane through the remaining four atoms by 0.651 (2) Å. The C1–C6 phenyl and C10–C15 benzene rings make dihedral angles of 82.96 (13) and 70.97 (12)°, respectively, with the mean plane of oxazolidine ring. The bond lengths and angles are in normal ranges (Allen et al., 1987) and in agreement with those reported by Asaruddin et al. (2010).

In the crystal structure, adjacent molecules are connected via intermolecular O2—H2···O1 and C15—H15A···O2 hydrogen bonds and C18—H18A···Cg2 interactions (Table 1) to form a chain along the [010] direction; Cg2 is the centroid of the C1–C6 ring.

Related literature top

For the synthesis and closely related structures, see: Asaruddin et al. (2010); Diwischeck et al. (2003); Khruscheva et al. (1997); Duffy et al. (2004). For therapeutic properties of oxazolidine derivatives, see: Moloney et al. (1998); Wang et al. (2010); Nakano et al. (2010); Fulop et al. (2004); Panneerselvam (2011). For standard bond lengths, see: Allen et al. (1987). For the low-temperature device used in the data collection, see: Cosier & Glazer (1986).

Experimental top

Following a modified method (Asaruddin et al., 2010; Diwischeck et al., 2003; Khruscheva et al., 1997), (1S,2S)-2-methylamino-1-phenylpropan-1-ol (0.17 g, 1 mmol) was mixed with 3-bromo-4-hydroxy-5-methoxybenzaldehyde (0.23 g, 1 mmol) in a two-round neck bottom flask. The mixture was dissolved in methanol (4 ml) and molecular sieve 4Å (0.1 g) was added to the reaction mixture then the solution was refluxed at 333 K for 6 h. The solution was filtered and the solvent was evaporated in vacuo to give a crude product which was then recrystallized three times from methanol to give colourless blocks with a yield 11%. These were washed with n-hexane and dried overnight to afford single crystals suitable for X-ray analysis.

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 the title compound, with displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The molecular packing of the title compound viewed down the a axis.

2-Bromo-4-(3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-yl)-6-methoxyphenol top

Crystal data top

C₁₈H₂₀BrNO₃	F(000) = 776
M_r = 378.26	D_x = 1.430 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8965 reflections
a = 7.8056 (4) Å	θ = 2.0–24.9°
b = 11.9034 (6) Å	µ = 2.35 mm⁻¹
c = 18.9109 (9) Å	T = 100 K
V = 1757.07 (15) Å³	Block, colourless
Z = 4	0.50 × 0.36 × 0.23 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3074 independent reflections
Radiation source: fine-focus sealed tube	2935 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
Detector resolution: 83.66 pixels mm^-1	θ_max = 24.9°, θ_min = 2.0°
ϕ and ω scan	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→14
T_min = 0.383, T_max = 0.618	l = −22→22
10569 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.023	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.056	w = 1/[σ²(F_o²) + (0.0197P)²] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
3074 reflections	Δρ_max = 0.32 e Å⁻³
215 parameters	Δρ_min = −0.26 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1283 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.004 (7)

Crystal data top

C₁₈H₂₀BrNO₃	V = 1757.07 (15) Å³
M_r = 378.26	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.8056 (4) Å	µ = 2.35 mm⁻¹
b = 11.9034 (6) Å	T = 100 K
c = 18.9109 (9) Å	0.50 × 0.36 × 0.23 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3074 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2935 reflections with I > 2σ(I)
T_min = 0.383, T_max = 0.618	R_int = 0.037
10569 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.056	Δρ_max = 0.32 e Å⁻³
S = 1.08	Δρ_min = −0.26 e Å⁻³
3074 reflections	Absolute structure: Flack (1983), 1283 Friedel pairs
215 parameters	Absolute structure parameter: 0.004 (7)
1 restraint

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 100.0 (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
Br1	0.58037 (3)	0.865565 (17)	0.942297 (10)	0.02402 (8)
O1	0.2217 (2)	0.40943 (12)	0.84900 (7)	0.0161 (3)
O2	0.6507 (2)	0.85865 (13)	0.78478 (7)	0.0187 (3)
O3	0.5513 (2)	0.71024 (11)	0.68917 (7)	0.0195 (3)
N1	0.0154 (3)	0.54199 (15)	0.83295 (9)	0.0179 (4)
C1	0.0051 (3)	0.1430 (2)	0.85221 (12)	0.0259 (5)
H1A	−0.0140	0.1381	0.8027	0.031*
C2	−0.0108 (4)	0.0473 (2)	0.89404 (16)	0.0362 (7)
H2A	−0.0416	−0.0224	0.8732	0.043*
C3	0.0182 (4)	0.0542 (2)	0.96587 (14)	0.0365 (7)
H3A	0.0072	−0.0110	0.9944	0.044*
C4	0.0633 (4)	0.1557 (2)	0.99672 (12)	0.0341 (6)
H4A	0.0831	0.1600	1.0462	0.041*
C5	0.0792 (4)	0.25110 (19)	0.95494 (11)	0.0257 (5)
H5A	0.1110	0.3205	0.9760	0.031*
C6	0.0490 (3)	0.24580 (18)	0.88251 (10)	0.0191 (5)
C7	0.0610 (3)	0.34994 (17)	0.83700 (10)	0.0170 (5)
H7A	0.0563	0.3265	0.7862	0.020*
C8	0.1793 (3)	0.52295 (17)	0.86771 (10)	0.0165 (5)
H8A	0.1630	0.5277	0.9201	0.020*
C9	−0.0781 (3)	0.43775 (18)	0.84969 (10)	0.0191 (5)
H9A	−0.1098	0.4379	0.9009	0.023*
C10	0.3140 (3)	0.60567 (17)	0.84574 (10)	0.0152 (5)
C11	0.3775 (3)	0.68157 (17)	0.89478 (11)	0.0167 (5)
H11A	0.3434	0.6764	0.9429	0.020*
C12	0.4899 (3)	0.76443 (18)	0.87389 (10)	0.0162 (5)
C13	0.5436 (3)	0.77558 (17)	0.80434 (10)	0.0153 (4)
C14	0.4837 (3)	0.69524 (17)	0.75520 (10)	0.0149 (4)
C15	0.3686 (3)	0.61278 (17)	0.77486 (10)	0.0153 (4)
H15A	0.3264	0.5611	0.7407	0.018*
C16	−0.2384 (3)	0.4204 (2)	0.80546 (13)	0.0302 (6)
H16A	−0.3266	0.4741	0.8202	0.045*
H16B	−0.2808	0.3437	0.8122	0.045*
H16C	−0.2112	0.4324	0.7554	0.045*
C17	−0.0712 (3)	0.64373 (18)	0.85614 (11)	0.0258 (5)
H17A	0.0013	0.7090	0.8461	0.039*
H17B	−0.0931	0.6394	0.9071	0.039*
H17C	−0.1802	0.6513	0.8309	0.039*
C18	0.5220 (3)	0.62188 (19)	0.63849 (10)	0.0224 (5)
H18A	0.5904	0.6361	0.5960	0.034*
H18B	0.4003	0.6199	0.6259	0.034*
H18C	0.5554	0.5496	0.6591	0.034*
H2	0.659 (3)	0.856 (2)	0.74000 (15)	0.022 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03139 (14)	0.02299 (12)	0.01767 (10)	−0.00772 (11)	−0.00524 (10)	−0.00103 (8)
O1	0.0127 (8)	0.0156 (7)	0.0200 (7)	−0.0001 (7)	0.0011 (6)	0.0004 (5)
O2	0.0203 (8)	0.0183 (8)	0.0176 (7)	−0.0032 (7)	0.0025 (6)	0.0005 (6)
O3	0.0228 (10)	0.0188 (8)	0.0171 (6)	−0.0038 (7)	0.0049 (7)	−0.0016 (5)
N1	0.0126 (10)	0.0177 (10)	0.0234 (8)	−0.0018 (8)	−0.0014 (8)	0.0019 (7)
C1	0.0216 (13)	0.0234 (12)	0.0328 (11)	−0.0021 (11)	−0.0001 (10)	−0.0009 (10)
C2	0.0318 (16)	0.0194 (13)	0.0574 (16)	−0.0070 (12)	0.0011 (14)	0.0022 (11)
C3	0.0310 (16)	0.0269 (14)	0.0517 (15)	−0.0027 (12)	0.0041 (13)	0.0184 (11)
C4	0.0358 (16)	0.0388 (15)	0.0278 (11)	0.0018 (14)	0.0042 (12)	0.0111 (10)
C5	0.0295 (14)	0.0222 (11)	0.0252 (10)	0.0001 (11)	0.0019 (12)	0.0020 (8)
C6	0.0132 (13)	0.0196 (11)	0.0245 (10)	0.0004 (10)	0.0034 (10)	0.0023 (8)
C7	0.0159 (12)	0.0190 (11)	0.0160 (8)	−0.0046 (10)	−0.0001 (9)	−0.0016 (8)
C8	0.0167 (13)	0.0180 (11)	0.0150 (9)	0.0035 (10)	−0.0007 (9)	−0.0005 (8)
C9	0.0143 (11)	0.0219 (11)	0.0211 (9)	−0.0030 (11)	0.0023 (10)	0.0026 (8)
C10	0.0110 (11)	0.0163 (11)	0.0184 (9)	0.0043 (9)	−0.0003 (8)	0.0024 (8)
C11	0.0165 (12)	0.0177 (10)	0.0159 (9)	0.0022 (9)	−0.0006 (9)	0.0031 (8)
C12	0.0146 (12)	0.0173 (11)	0.0167 (9)	0.0016 (9)	−0.0039 (9)	−0.0036 (8)
C13	0.0105 (12)	0.0149 (10)	0.0204 (9)	0.0012 (9)	−0.0012 (9)	0.0026 (7)
C14	0.0118 (11)	0.0167 (11)	0.0163 (9)	0.0040 (9)	0.0005 (9)	0.0015 (8)
C15	0.0149 (11)	0.0136 (11)	0.0174 (9)	0.0034 (9)	−0.0026 (9)	−0.0004 (7)
C16	0.0171 (13)	0.0353 (14)	0.0383 (12)	−0.0027 (12)	−0.0068 (12)	0.0025 (10)
C17	0.0178 (12)	0.0250 (12)	0.0345 (11)	0.0039 (14)	0.0010 (11)	0.0037 (9)
C18	0.0256 (12)	0.0229 (12)	0.0186 (9)	−0.0033 (11)	0.0040 (9)	−0.0058 (9)

Geometric parameters (Å, º) top

Br1—C12	1.903 (2)	C7—H7A	1.0000
O1—C8	1.435 (3)	C8—C10	1.499 (3)
O1—C7	1.458 (3)	C8—H8A	1.0000
O2—C13	1.347 (3)	C9—C16	1.519 (4)
O2—H2	0.8499 (10)	C9—H9A	1.0000
O3—C14	1.367 (2)	C10—C11	1.386 (3)
O3—C18	1.441 (2)	C10—C15	1.409 (3)
N1—C17	1.455 (3)	C11—C12	1.378 (3)
N1—C8	1.456 (3)	C11—H11A	0.9500
N1—C9	1.474 (3)	C12—C13	1.387 (3)
C1—C2	1.392 (3)	C13—C14	1.413 (3)
C1—C6	1.394 (3)	C14—C15	1.382 (3)
C1—H1A	0.9500	C15—H15A	0.9500
C2—C3	1.379 (4)	C16—H16A	0.9800
C2—H2A	0.9500	C16—H16B	0.9800
C3—C4	1.387 (4)	C16—H16C	0.9800
C3—H3A	0.9500	C17—H17A	0.9800
C4—C5	1.389 (3)	C17—H17B	0.9800
C4—H4A	0.9500	C17—H17C	0.9800
C5—C6	1.391 (3)	C18—H18A	0.9800
C5—H5A	0.9500	C18—H18B	0.9800
C6—C7	1.512 (3)	C18—H18C	0.9800
C7—C9	1.526 (3)

C8—O1—C7	107.31 (16)	N1—C9—H9A	109.2
C13—O2—H2	107.2 (18)	C16—C9—H9A	109.2
C14—O3—C18	116.80 (16)	C7—C9—H9A	109.2
C17—N1—C8	113.71 (18)	C11—C10—C15	119.30 (19)
C17—N1—C9	113.94 (18)	C11—C10—C8	119.56 (18)
C8—N1—C9	101.95 (17)	C15—C10—C8	120.99 (18)
C2—C1—C6	120.4 (2)	C12—C11—C10	120.15 (19)
C2—C1—H1A	119.8	C12—C11—H11A	119.9
C6—C1—H1A	119.8	C10—C11—H11A	119.9
C3—C2—C1	119.8 (2)	C11—C12—C13	122.20 (19)
C3—C2—H2A	120.1	C11—C12—Br1	119.62 (15)
C1—C2—H2A	120.1	C13—C12—Br1	118.16 (16)
C2—C3—C4	120.5 (2)	O2—C13—C12	121.22 (18)
C2—C3—H3A	119.7	O2—C13—C14	121.44 (18)
C4—C3—H3A	119.7	C12—C13—C14	117.32 (19)
C3—C4—C5	119.7 (2)	O3—C14—C15	126.11 (18)
C3—C4—H4A	120.2	O3—C14—C13	112.63 (18)
C5—C4—H4A	120.2	C15—C14—C13	121.26 (18)
C4—C5—C6	120.5 (2)	C14—C15—C10	119.68 (19)
C4—C5—H5A	119.7	C14—C15—H15A	120.2
C6—C5—H5A	119.7	C10—C15—H15A	120.2
C5—C6—C1	119.1 (2)	C9—C16—H16A	109.5
C5—C6—C7	120.85 (18)	C9—C16—H16B	109.5
C1—C6—C7	120.07 (18)	H16A—C16—H16B	109.5
O1—C7—C6	111.27 (17)	C9—C16—H16C	109.5
O1—C7—C9	104.75 (16)	H16A—C16—H16C	109.5
C6—C7—C9	115.34 (19)	H16B—C16—H16C	109.5
O1—C7—H7A	108.4	N1—C17—H17A	109.5
C6—C7—H7A	108.4	N1—C17—H17B	109.5
C9—C7—H7A	108.4	H17A—C17—H17B	109.5
O1—C8—N1	103.74 (17)	N1—C17—H17C	109.5
O1—C8—C10	112.86 (18)	H17A—C17—H17C	109.5
N1—C8—C10	112.88 (17)	H17B—C17—H17C	109.5
O1—C8—H8A	109.1	O3—C18—H18A	109.5
N1—C8—H8A	109.1	O3—C18—H18B	109.5
C10—C8—H8A	109.1	H18A—C18—H18B	109.5
N1—C9—C16	113.81 (18)	O3—C18—H18C	109.5
N1—C9—C7	101.0 (2)	H18A—C18—H18C	109.5
C16—C9—C7	113.98 (18)	H18B—C18—H18C	109.5

C6—C1—C2—C3	−0.5 (5)	C6—C7—C9—N1	149.13 (17)
C1—C2—C3—C4	0.0 (5)	O1—C7—C9—C16	148.90 (18)
C2—C3—C4—C5	0.0 (5)	C6—C7—C9—C16	−88.4 (2)
C3—C4—C5—C6	0.5 (5)	O1—C8—C10—C11	−129.0 (2)
C4—C5—C6—C1	−1.0 (4)	N1—C8—C10—C11	113.7 (2)
C4—C5—C6—C7	178.2 (3)	O1—C8—C10—C15	55.5 (3)
C2—C1—C6—C5	1.0 (4)	N1—C8—C10—C15	−61.8 (3)
C2—C1—C6—C7	−178.2 (2)	C15—C10—C11—C12	1.4 (3)
C8—O1—C7—C6	−124.92 (17)	C8—C10—C11—C12	−174.2 (2)
C8—O1—C7—C9	0.36 (18)	C10—C11—C12—C13	0.0 (3)
C5—C6—C7—O1	50.7 (3)	C10—C11—C12—Br1	−178.39 (17)
C1—C6—C7—O1	−130.1 (2)	C11—C12—C13—O2	178.6 (2)
C5—C6—C7—C9	−68.4 (3)	Br1—C12—C13—O2	−3.0 (3)
C1—C6—C7—C9	110.7 (2)	C11—C12—C13—C14	−2.5 (3)
C7—O1—C8—N1	−27.71 (18)	Br1—C12—C13—C14	175.97 (16)
C7—O1—C8—C10	−150.23 (16)	C18—O3—C14—C15	−10.8 (3)
C17—N1—C8—O1	167.85 (16)	C18—O3—C14—C13	169.59 (19)
C9—N1—C8—O1	44.77 (18)	O2—C13—C14—O3	2.2 (3)
C17—N1—C8—C10	−69.6 (2)	C12—C13—C14—O3	−176.71 (19)
C9—N1—C8—C10	167.27 (17)	O2—C13—C14—C15	−177.4 (2)
C17—N1—C9—C16	71.3 (2)	C12—C13—C14—C15	3.6 (3)
C8—N1—C9—C16	−165.77 (19)	O3—C14—C15—C10	178.0 (2)
C17—N1—C9—C7	−166.13 (17)	C13—C14—C15—C10	−2.3 (3)
C8—N1—C9—C7	−43.20 (18)	C11—C10—C15—C14	−0.2 (3)
O1—C7—C9—N1	26.45 (18)	C8—C10—C15—C14	175.3 (2)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C1–C6 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.85 (1)	2.03 (1)	2.7853 (19)	148 (2)
C15—H15A···O2ⁱⁱ	0.95	2.46	3.232 (3)	138
C18—H18A···Cg2ⁱ	0.98	2.96	3.679 (3)	131

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

Experimental details

Crystal data
Chemical formula	C₁₈H₂₀BrNO₃
M_r	378.26
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	7.8056 (4), 11.9034 (6), 18.9109 (9)
V (Å³)	1757.07 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.35
Crystal size (mm)	0.50 × 0.36 × 0.23

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.383, 0.618
No. of measured, independent and observed [I > 2σ(I)] reflections	10569, 3074, 2935
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.592

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.056, 1.08
No. of reflections	3074
No. of parameters	215
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.26
Absolute structure	Flack (1983), 1283 Friedel pairs
Absolute structure parameter	0.004 (7)

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

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C1–C6 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.850 (4)	2.026 (13)	2.7853 (19)	148 (2)
C15—H15A···O2ⁱⁱ	0.95	2.46	3.232 (3)	138
C18—H18A···Cg2ⁱ	0.98	2.96	3.679 (3)	131

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

Acknowledgements

MH, HAW and ASAR acknowledge the Malaysia Ministry of Science, Technology and Innovations (MOSTI) for funding the synthetic chemistry work under the R&D initiative grant Nos. 09-05-lfn-meb-004 and 304/PFARMASI/650544/I121. MH thanks Universiti Sains Malaysia for the award of a postgraduate fellowship.

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Volume 68| Part 1| January 2012| Pages o35-o36

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