7-(6-Bromo­hex­yloxy)-4-methyl-2H-chromen-2-one

Zhang, H.-Z.; Li, Q.-X.; Yin, B.-T.; Zhou, C.-H.

doi:10.1107/S1600536812020442

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1709

doi:10.1107/S1600536812020442

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7-(6-Bromohexyloxy)-4-methyl-2H-chromen-2-one

Hui-Zhen Zhang,^a Qing-Xia Li,^a Ben-Tao Yin ^a and Cheng-He Zhou ^a ^*

^aLaboratory of Bioorganic & Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People's Republic of China
^*Correspondence e-mail: zhouch@swu.edu.cn

(Received 17 April 2012; accepted 7 May 2012; online 12 May 2012)

In the title molecule, C₁₆H₁₉BrO₃, all non-H atoms apart from the Br atom are approximately coplanar, with a maximum deviation of 0.242 (4) Å. The C—C—C—Br torsion angle is 66.5 (4)°.

Related literature

For the pharmacological activity of coumarin compounds, see: Wu et al. (2009 ); Shi & Zhou (2011 ). For details of the synthesis, see: Shi et al. (2011 ). For a related structure, see: Zhang et al. (2011 ).

Experimental

Crystal data

C₁₆H₁₉BrO₃
M_r = 339.22
Monoclinic, C 2/c
a = 15.681 (5) Å
b = 9.540 (3) Å
c = 22.104 (7) Å
β = 110.201 (6)°
V = 3103.3 (18) Å³
Z = 8
Mo Kα radiation
μ = 2.65 mm⁻¹
T = 296 K
0.22 × 0.18 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.593, T_max = 0.692
8381 measured reflections
3051 independent reflections
1921 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.115
S = 1.01
3051 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Data collection: APEX2 (Sheldrick, 2008 ); cell refinement: SAINT (Sheldrick, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812020442/lh5459sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812020442/lh5459Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812020442/lh5459Isup3.cml

checkCIF report

Comment top

Coumarin compounds are important in medicinal chemistry due to their extensive potential applications in antibacterial, antifungal, antiviral, anti-tubercular, anti-malarial, anticancer and anti-inflammatory fields (Wu, et al., 2009; Shi & Zhou, 2011). Our interest is to develop novel coumarin compounds as antimicrobial agents and some structral related coumarin-triazoles have been reported as potential bioactive agents (Shi, et al., 2011; Zhang, et al., 2011). Herein, we report the crystal structure of the title compound (I).

The molecular structure of (I) is shown in Fig. 1. With the exception of the Br atom, all non-hydrogen atoms are approximately co-planar with a maximum deviation of 0.242 (4)Å (C16). The C14—C15—C16—Br1 torsion angle is 66.5 (4)Å.

Related literature top

For the pharmacological activity of coumarin compounds, see: Wu et al. (2009); Shi & Zhou (2011). For details of the synthesis, see: Shi et al. (2011). For a related structure, see: Zhang et al. (2011).

Experimental top

Compound (I) was prepared according to the procedure of Shi & Zhou (2011). Single crystals were grown by slow evaporation of a solution of (I) in CHCl₃ at room temperature.

Computing details top

Data collection: APEX2 (Sheldrick, 2008); cell refinement: SAINT (Sheldrick, 2008); data reduction: SAINT (Sheldrick, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), showing displacement ellipsoids drawn at the 50% probability level.

7-(6-Bromohexyloxy)-4-methyl-2H-chromen-2-one top

Crystal data top

C₁₆H₁₉BrO₃	F(000) = 1392
M_r = 339.22	D_x = 1.452 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2005 reflections
a = 15.681 (5) Å	θ = 2.6–22.1°
b = 9.540 (3) Å	µ = 2.65 mm⁻¹
c = 22.104 (7) Å	T = 296 K
β = 110.201 (6)°	Block, colorless
V = 3103.3 (18) Å³	0.22 × 0.18 × 0.15 mm
Z = 8

Data collection top

Bruker APEXII CCD diffractometer	3051 independent reflections
Radiation source: fine-focus sealed tube	1921 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −19→19
T_min = 0.593, T_max = 0.692	k = −9→11
8381 measured reflections	l = −27→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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0527P)² + 2.7774P] where P = (F_o² + 2F_c²)/3
3051 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

C₁₆H₁₉BrO₃	V = 3103.3 (18) Å³
M_r = 339.22	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 15.681 (5) Å	µ = 2.65 mm⁻¹
b = 9.540 (3) Å	T = 296 K
c = 22.104 (7) Å	0.22 × 0.18 × 0.15 mm
β = 110.201 (6)°

Data collection top

Bruker APEXII CCD diffractometer	3051 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1921 reflections with I > 2σ(I)
T_min = 0.593, T_max = 0.692	R_int = 0.028
8381 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.01	Δρ_max = 0.48 e Å⁻³
3051 reflections	Δρ_min = −0.53 e Å⁻³
181 parameters

Special details top

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	0.13272 (3)	0.92653 (5)	0.02243 (2)	0.0880 (2)
C1	0.7117 (2)	−0.1670 (3)	0.24911 (16)	0.0537 (8)
C2	0.6618 (2)	−0.2939 (3)	0.22745 (15)	0.0545 (8)
H2A	0.6926	−0.3787	0.2379	0.065*
C3	0.5727 (2)	−0.2965 (3)	0.19283 (15)	0.0513 (8)
C4	0.5235 (3)	−0.4315 (3)	0.1708 (2)	0.0741 (11)
H4A	0.5654	−0.5082	0.1847	0.111*
H4B	0.4973	−0.4319	0.1246	0.111*
H4C	0.4763	−0.4412	0.1889	0.111*
C5	0.5242 (2)	−0.1647 (3)	0.17747 (14)	0.0442 (7)
C6	0.57263 (19)	−0.0413 (3)	0.19839 (14)	0.0427 (7)
C7	0.5329 (2)	0.0882 (3)	0.18675 (15)	0.0478 (7)
H7A	0.5674	0.1687	0.2012	0.057*
C8	0.4408 (2)	0.0971 (3)	0.15309 (15)	0.0514 (8)
C9	0.3895 (2)	−0.0240 (3)	0.13091 (15)	0.0527 (8)
H9A	0.3274	−0.0181	0.1083	0.063*
C10	0.4319 (2)	−0.1512 (3)	0.14297 (15)	0.0528 (8)
H10A	0.3978	−0.2316	0.1275	0.063*
C11	0.3099 (2)	0.2471 (3)	0.11206 (17)	0.0602 (9)
H11A	0.2765	0.1966	0.1348	0.072*
H11B	0.2915	0.2118	0.0683	0.072*
C12	0.2914 (2)	0.4009 (3)	0.11200 (19)	0.0612 (9)
H12A	0.3306	0.4497	0.0932	0.073*
H12B	0.3073	0.4324	0.1563	0.073*
C13	0.1935 (2)	0.4414 (3)	0.07516 (16)	0.0557 (8)
H13A	0.1779	0.4142	0.0303	0.067*
H13B	0.1537	0.3911	0.0928	0.067*
C14	0.1785 (2)	0.5971 (3)	0.07899 (17)	0.0584 (9)
H14A	0.1936	0.6231	0.1239	0.070*
H14B	0.2199	0.6466	0.0625	0.070*
C15	0.0828 (2)	0.6447 (3)	0.04209 (17)	0.0579 (8)
H15A	0.0713	0.6332	−0.0036	0.069*
H15B	0.0407	0.5844	0.0533	0.069*
C16	0.0638 (2)	0.7941 (4)	0.05454 (19)	0.0674 (10)
H16A	0.0790	0.8079	0.1005	0.081*
H16B	−0.0006	0.8128	0.0339	0.081*
O1	0.79161 (16)	−0.1577 (2)	0.27985 (13)	0.0766 (8)
O2	0.66442 (13)	−0.0436 (2)	0.23286 (10)	0.0503 (5)
O3	0.40587 (14)	0.2292 (2)	0.14399 (12)	0.0649 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0703 (3)	0.0743 (3)	0.1032 (4)	0.0001 (2)	0.0092 (2)	0.0270 (2)
C1	0.0448 (19)	0.053 (2)	0.059 (2)	0.0053 (15)	0.0121 (16)	0.0118 (16)
C2	0.047 (2)	0.0450 (18)	0.063 (2)	0.0062 (15)	0.0084 (16)	0.0043 (15)
C3	0.050 (2)	0.0476 (18)	0.0523 (19)	0.0003 (14)	0.0122 (15)	−0.0034 (15)
C4	0.061 (2)	0.055 (2)	0.088 (3)	0.0001 (17)	0.003 (2)	−0.0139 (19)
C5	0.0413 (17)	0.0469 (17)	0.0416 (16)	0.0011 (13)	0.0107 (14)	−0.0022 (13)
C6	0.0331 (16)	0.0509 (18)	0.0416 (17)	0.0017 (13)	0.0097 (13)	0.0029 (13)
C7	0.0411 (17)	0.0485 (18)	0.0521 (19)	−0.0018 (14)	0.0141 (14)	0.0044 (14)
C8	0.0445 (18)	0.056 (2)	0.0533 (19)	0.0111 (15)	0.0160 (15)	0.0096 (15)
C9	0.0376 (17)	0.059 (2)	0.0545 (19)	0.0040 (15)	0.0065 (15)	−0.0024 (16)
C10	0.0442 (18)	0.0516 (19)	0.057 (2)	−0.0047 (14)	0.0096 (15)	−0.0085 (15)
C11	0.0435 (19)	0.064 (2)	0.070 (2)	0.0135 (16)	0.0152 (16)	0.0051 (18)
C12	0.048 (2)	0.057 (2)	0.077 (2)	0.0098 (15)	0.0192 (18)	0.0057 (17)
C13	0.0495 (19)	0.057 (2)	0.058 (2)	0.0099 (15)	0.0151 (16)	0.0016 (16)
C14	0.0501 (19)	0.055 (2)	0.065 (2)	0.0062 (15)	0.0135 (17)	0.0026 (16)
C15	0.052 (2)	0.056 (2)	0.063 (2)	0.0062 (16)	0.0154 (17)	0.0027 (16)
C16	0.057 (2)	0.065 (2)	0.080 (3)	0.0135 (17)	0.0220 (19)	0.0094 (19)
O1	0.0404 (14)	0.0630 (16)	0.104 (2)	0.0007 (11)	−0.0028 (14)	0.0119 (14)
O2	0.0358 (12)	0.0467 (12)	0.0610 (14)	−0.0013 (9)	0.0070 (10)	0.0049 (10)
O3	0.0437 (13)	0.0537 (13)	0.0888 (17)	0.0102 (10)	0.0120 (12)	0.0073 (12)

Geometric parameters (Å, º) top

Br1—C16	1.949 (4)	C9—H9A	0.9300
C1—O1	1.205 (4)	C10—H10A	0.9300
C1—O2	1.371 (4)	C11—O3	1.435 (4)
C1—C2	1.431 (4)	C11—C12	1.496 (4)
C2—C3	1.341 (4)	C11—H11A	0.9700
C2—H2A	0.9300	C11—H11B	0.9700
C3—C5	1.448 (4)	C12—C13	1.520 (4)
C3—C4	1.494 (4)	C12—H12A	0.9700
C4—H4A	0.9600	C12—H12B	0.9700
C4—H4B	0.9600	C13—C14	1.511 (4)
C4—H4C	0.9600	C13—H13A	0.9700
C5—C6	1.391 (4)	C13—H13B	0.9700
C5—C10	1.390 (4)	C14—C15	1.510 (4)
C6—O2	1.377 (3)	C14—H14A	0.9700
C6—C7	1.367 (4)	C14—H14B	0.9700
C7—C8	1.380 (4)	C15—C16	1.501 (5)
C7—H7A	0.9300	C15—H15A	0.9700
C8—O3	1.362 (4)	C15—H15B	0.9700
C8—C9	1.397 (4)	C16—H16A	0.9700
C9—C10	1.365 (4)	C16—H16B	0.9700

O1—C1—O2	116.6 (3)	O3—C11—H11B	110.4
O1—C1—C2	126.4 (3)	C12—C11—H11B	110.4
O2—C1—C2	117.0 (3)	H11A—C11—H11B	108.6
C3—C2—C1	123.2 (3)	C11—C12—C13	114.1 (3)
C3—C2—H2A	118.4	C11—C12—H12A	108.7
C1—C2—H2A	118.4	C13—C12—H12A	108.7
C2—C3—C5	118.5 (3)	C11—C12—H12B	108.7
C2—C3—C4	121.4 (3)	C13—C12—H12B	108.7
C5—C3—C4	120.1 (3)	H12A—C12—H12B	107.6
C3—C4—H4A	109.5	C14—C13—C12	111.6 (3)
C3—C4—H4B	109.5	C14—C13—H13A	109.3
H4A—C4—H4B	109.5	C12—C13—H13A	109.3
C3—C4—H4C	109.5	C14—C13—H13B	109.3
H4A—C4—H4C	109.5	C12—C13—H13B	109.3
H4B—C4—H4C	109.5	H13A—C13—H13B	108.0
C6—C5—C10	116.7 (3)	C15—C14—C13	114.2 (3)
C6—C5—C3	118.4 (3)	C15—C14—H14A	108.7
C10—C5—C3	124.9 (3)	C13—C14—H14A	108.7
O2—C6—C7	116.1 (3)	C15—C14—H14B	108.7
O2—C6—C5	121.1 (3)	C13—C14—H14B	108.7
C7—C6—C5	122.8 (3)	H14A—C14—H14B	107.6
C8—C7—C6	118.7 (3)	C16—C15—C14	114.2 (3)
C8—C7—H7A	120.6	C16—C15—H15A	108.7
C6—C7—H7A	120.6	C14—C15—H15A	108.7
O3—C8—C7	115.5 (3)	C16—C15—H15B	108.7
O3—C8—C9	124.1 (3)	C14—C15—H15B	108.7
C7—C8—C9	120.5 (3)	H15A—C15—H15B	107.6
C10—C9—C8	118.9 (3)	C15—C16—Br1	112.3 (2)
C10—C9—H9A	120.5	C15—C16—H16A	109.2
C8—C9—H9A	120.5	Br1—C16—H16A	109.2
C9—C10—C5	122.3 (3)	C15—C16—H16B	109.2
C9—C10—H10A	118.8	Br1—C16—H16B	109.2
C5—C10—H10A	118.8	H16A—C16—H16B	107.9
O3—C11—C12	106.6 (3)	C1—O2—C6	121.8 (2)
O3—C11—H11A	110.4	C8—O3—C11	118.9 (3)
C12—C11—H11A	110.4

O1—C1—C2—C3	−179.4 (3)	C7—C8—C9—C10	−0.1 (5)
O2—C1—C2—C3	−0.1 (5)	C8—C9—C10—C5	1.1 (5)
C1—C2—C3—C5	−1.1 (5)	C6—C5—C10—C9	−1.3 (5)
C1—C2—C3—C4	179.5 (3)	C3—C5—C10—C9	178.8 (3)
C2—C3—C5—C6	1.1 (4)	O3—C11—C12—C13	175.4 (3)
C4—C3—C5—C6	−179.5 (3)	C11—C12—C13—C14	177.9 (3)
C2—C3—C5—C10	−179.0 (3)	C12—C13—C14—C15	178.8 (3)
C4—C3—C5—C10	0.5 (5)	C13—C14—C15—C16	170.5 (3)
C10—C5—C6—O2	−179.9 (3)	C14—C15—C16—Br1	66.5 (4)
C3—C5—C6—O2	0.0 (4)	O1—C1—O2—C6	−179.3 (3)
C10—C5—C6—C7	0.5 (4)	C2—C1—O2—C6	1.3 (4)
C3—C5—C6—C7	−179.5 (3)	C7—C6—O2—C1	178.3 (3)
O2—C6—C7—C8	−179.2 (3)	C5—C6—O2—C1	−1.3 (4)
C5—C6—C7—C8	0.3 (5)	C7—C8—O3—C11	−177.1 (3)
C6—C7—C8—O3	179.3 (3)	C9—C8—O3—C11	2.7 (5)
C6—C7—C8—C9	−0.6 (5)	C12—C11—O3—C8	177.3 (3)
O3—C8—C9—C10	−179.9 (3)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₉BrO₃
M_r	339.22
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	15.681 (5), 9.540 (3), 22.104 (7)
β (°)	110.201 (6)
V (Å³)	3103.3 (18)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.65
Crystal size (mm)	0.22 × 0.18 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.593, 0.692
No. of measured, independent and observed [I > 2σ(I)] reflections	8381, 3051, 1921
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.115, 1.01
No. of reflections	3051
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.53

Computer programs: APEX2 (Sheldrick, 2008), SAINT (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was partially supported by the National Natural Science Foundation of China (No. 21172181), the Key Program of the Natural Science Foundation of Chongqing (CSTC2012jjB10026), the Specialized Research Fund for the Doctoral Program of Higher Education of China (SRFDP 20110182110007) and the Research Funds for the Central Universities (XDJK2012B026).

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shi, Y. & Zhou, C.-H. (2011). Bioorg. Med. Chem. Lett. 21, 956–960. Web of Science CrossRef CAS PubMed Google Scholar
Shi, Y., Zhou, C.-H., Zhou, X.-D., Geng, R.-X. & Ji, Q.-G. (2011). Acta Pharm. Sin. 46, 798–810. CAS Google Scholar
Wu, L., Wang, X., Xu, W., Farzaneh, F. & Xu, R. (2009). Curr. Med. Chem. 16, 4236–4260. Web of Science CrossRef PubMed CAS Google Scholar
Zhang, Y.-Y., Shi, Y. & Zhou, C.-H. (2011). Acta Cryst. E67, o892. Web of Science CSD CrossRef IUCr Journals Google Scholar