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

Abstract

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,

• a = 15.681 (5) Å

• b = 9.540 (3) Å

• c = 22.104 (7) Å

• β = 110.201 (6)°

• V = 3103.3 (18) ų

• 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[F ² > 2σ(F ²)] = 0.042

• wR(F ²) = 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.

Supplementary Material

Supplementary material file. DOI: 10.1107/S1600536812020442/lh5459Isup3.cml

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

supplementary crystallographic information

Comment

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.

Experimental

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.

Refinement

H atoms were placed at calculated position with C—H = 0.93 Å (aromatic), 0.96 Å (methyl) and 0.97 Å (methylene). The U_iso(H) values were set to 1.2U_eq(C) or 1.5U_eq(C_methyl).

Figures

Fig. 1.

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

Crystal data

C16H19BrO3	F(000) = 1392
Mr = 339.22	Dx = 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

Bruker APEXII CCD diffractometer	3051 independent reflections
Radiation source: fine-focus sealed tube	1921 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 26.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −19→19
Tmin = 0.593, Tmax = 0.692	k = −9→11
8381 measured reflections	l = −27→20

Refinement

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(Fo2) + (0.0527P)2 + 2.7774P] where P = (Fo2 + 2Fc2)/3
3051 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.53 e Å−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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)

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)