4-Bromo-methyl-6-tert-butyl-2H-chromen-2-one.

In the crystal structure of the title compound, C14H15BrO2, weak C-H⋯O inter-actions link the mol-ecules into zigzag chains extending along the c-axis direction. These chains are further assembled into (100) layers via π-π stacking inter-actions between inversion-related chromenone fragments [inter-planar distance = 3.376 (2) Å].

Related literature

For therapeutic properties of coumarin derivatives, see: Lacy & O’Kennedy (2004 ▶); Mustafa et al. (2011 ▶). For structural features of coumarins, see: Moorthy et al. (2003 ▶). For related structures, see: Gowda et al. (2010 ▶); Fun et al. (2011 ▶).

Experimental

Crystal data

C14H15BrO2

M = 295.17

Monoclinic,

a = 10.3311 (19) Å

b = 16.830 (3) Å

c = 7.3374 (14) Å

β = 97.518 (3)°

V = 1264.8 (4) Å3

Z = 4

Mo Kα radiation

μ = 3.24 mm−1

T = 100 K

0.18 × 0.16 × 0.16 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.593, T max = 0.625

7522 measured reflections

2737 independent reflections

2074 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.107

S = 1.05

2737 reflections

144 parameters

H-atom parameters constrained

Δρmax = 0.78 e Å−3

Δρmin = −0.36 e Å−3

Data collection: SMART (Bruker,1998 ▶); cell refinement: SAINT-Plus (Bruker,1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and CAMERON (Watkin et al., 1996) ▶; software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813015511/gk2575sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813015511/gk2575Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813015511/gk2575Isup3.cml

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

C14H15BrO2	F(000) = 600
Mr = 295.17	Dx = 1.550 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2074 reflections
a = 10.3311 (19) Å	θ = 2.3–27.0°
b = 16.830 (3) Å	µ = 3.24 mm−1
c = 7.3374 (14) Å	T = 100 K
β = 97.518 (3)°	Block, colourless
V = 1264.8 (4) Å3	0.18 × 0.16 × 0.16 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2737 independent reflections
Radiation source: fine-focus sealed tube	2074 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
ω scans	θmax = 27.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −13→12
Tmin = 0.593, Tmax = 0.625	k = −21→16
7522 measured reflections	l = −9→9

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0531P)2] where P = (Fo2 + 2Fc2)/3
2737 reflections	(Δ/σ)max < 0.001
144 parameters	Δρmax = 0.78 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

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 > 2σ(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.

	x	y	z	Uiso*/Ueq
C1	0.4032 (3)	0.13349 (18)	0.2373 (4)	0.0198 (7)
H1A	0.4081	0.0849	0.1624	0.024*
H1B	0.4768	0.1686	0.2164	0.024*
C2	0.5105 (3)	0.13683 (17)	0.7557 (4)	0.0190 (6)
C3	0.4913 (3)	0.15577 (18)	0.5616 (4)	0.0190 (6)
H3	0.5340	0.2011	0.5205	0.023*
C4	0.4148 (3)	0.11146 (17)	0.4361 (4)	0.0173 (6)
C5	0.2620 (3)	−0.00601 (18)	0.3828 (4)	0.0171 (6)
H5	0.2467	0.0057	0.2551	0.021*
C6	0.1996 (3)	−0.07068 (17)	0.4490 (4)	0.0187 (6)
C7	0.2270 (3)	−0.08765 (18)	0.6383 (4)	0.0215 (7)
H7	0.1870	−0.1324	0.6869	0.026*
C8	0.3104 (3)	−0.04076 (18)	0.7543 (4)	0.0215 (7)
H8	0.3276	−0.0530	0.8816	0.026*
C9	0.3687 (3)	0.02395 (17)	0.6843 (4)	0.0182 (6)
C10	0.3472 (3)	0.04295 (17)	0.4984 (4)	0.0161 (6)
C11	0.1007 (3)	−0.12192 (18)	0.3272 (4)	0.0210 (7)
C12	−0.0343 (3)	−0.11188 (14)	0.3930 (5)	0.0368 (9)
H12A	−0.0993	−0.1429	0.3137	0.055*
H12B	−0.0590	−0.0556	0.3871	0.055*
H12C	−0.0301	−0.1307	0.5200	0.055*
C13	0.1402 (3)	−0.21004 (14)	0.3427 (4)	0.0265 (7)
H13A	0.2251	−0.2171	0.2987	0.040*
H13B	0.0744	−0.2421	0.2680	0.040*
H13C	0.1465	−0.2269	0.4716	0.040*
C14	0.0902 (2)	−0.09867 (5)	0.12412 (5)	0.0305 (8)
H14A	0.1753	−0.1056	0.0808	0.046*
H14B	0.0632	−0.0430	0.1096	0.046*
H14C	0.0255	−0.1326	0.0520	0.046*
O1	0.45022 (6)	0.06915 (5)	0.80902 (6)	0.0197 (5)
O2	0.57521 (5)	0.17418 (5)	0.87563 (5)	0.0241 (5)
Br1	0.23783 (3)	0.18813 (2)	0.16045 (4)	0.03299 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0208 (16)	0.0200 (16)	0.0194 (15)	0.0001 (12)	0.0053 (12)	0.0043 (12)
C2	0.0205 (16)	0.0150 (15)	0.0227 (16)	0.0037 (12)	0.0073 (13)	−0.0024 (12)
C3	0.0178 (16)	0.0190 (16)	0.0205 (15)	0.0001 (12)	0.0036 (12)	0.0029 (12)
C4	0.0161 (15)	0.0153 (15)	0.0208 (15)	0.0031 (12)	0.0035 (12)	0.0013 (12)
C5	0.0165 (15)	0.0185 (16)	0.0164 (14)	0.0038 (12)	0.0018 (12)	0.0026 (11)
C6	0.0170 (15)	0.0157 (15)	0.0246 (16)	0.0017 (12)	0.0066 (12)	−0.0007 (12)
C7	0.0251 (17)	0.0155 (15)	0.0252 (16)	0.0007 (13)	0.0082 (13)	0.0021 (12)
C8	0.0257 (17)	0.0232 (17)	0.0164 (15)	0.0013 (13)	0.0063 (13)	0.0009 (12)
C9	0.0189 (16)	0.0202 (16)	0.0159 (14)	0.0016 (12)	0.0036 (12)	−0.0034 (12)
C10	0.0163 (15)	0.0146 (14)	0.0177 (14)	0.0035 (11)	0.0038 (11)	−0.0021 (11)
C11	0.0219 (16)	0.0153 (15)	0.0260 (17)	−0.0002 (12)	0.0046 (13)	0.0010 (13)
C12	0.0241 (19)	0.030 (2)	0.057 (2)	−0.0062 (15)	0.0107 (17)	−0.0144 (18)
C13	0.034 (2)	0.0228 (17)	0.0230 (17)	−0.0016 (14)	0.0032 (14)	−0.0003 (13)
C14	0.033 (2)	0.0261 (19)	0.0288 (18)	−0.0086 (15)	−0.0094 (15)	0.0047 (14)
O1	0.0252 (12)	0.0186 (11)	0.0149 (10)	−0.0026 (9)	0.0014 (9)	0.0002 (8)
O2	0.0283 (13)	0.0232 (12)	0.0202 (11)	−0.0030 (9)	0.0010 (9)	−0.0037 (9)
Br1	0.0305 (2)	0.0332 (2)	0.0326 (2)	0.00355 (15)	−0.00600 (15)	0.01003 (15)

C1—C4	1.494 (4)	C8—C9	1.376 (4)
C1—Br1	1.957 (3)	C8—H8	0.9500
C1—H1A	0.9900	C9—O1	1.387 (3)
C1—H1B	0.9900	C9—C10	1.390 (4)
C2—O2	1.209 (3)	C11—C14	1.531 (3)
C2—O1	1.379 (3)	C11—C13	1.539 (4)
C2—C3	1.448 (4)	C11—C12	1.544 (4)
C3—C4	1.356 (4)	C12—H12A	0.9800
C3—H3	0.9500	C12—H12B	0.9800
C4—C10	1.452 (4)	C12—H12C	0.9800
C5—C6	1.385 (4)	C13—H13A	0.9800
C5—C10	1.407 (4)	C13—H13B	0.9782
C5—H5	0.9500	C13—H13C	0.9819
C6—C7	1.410 (4)	C14—H14A	0.9800
C6—C11	1.532 (4)	C14—H14B	0.9800
C7—C8	1.378 (4)	C14—H14C	0.9800
C7—H7	0.9500
C4—C1—Br1	110.7 (2)	O1—C9—C10	121.8 (3)
C4—C1—H1A	109.5	C9—C10—C5	117.6 (3)
Br1—C1—H1A	109.5	C9—C10—C4	118.0 (3)
C4—C1—H1B	109.5	C5—C10—C4	124.3 (3)
Br1—C1—H1B	109.5	C14—C11—C6	112.4 (2)
H1A—C1—H1B	108.1	C14—C11—C13	107.6 (2)
O2—C2—O1	116.8 (2)	C6—C11—C13	110.4 (2)
O2—C2—C3	126.4 (3)	C14—C11—C12	109.0 (2)
O1—C2—C3	116.9 (2)	C6—C11—C12	108.4 (2)
C4—C3—C2	122.7 (3)	C13—C11—C12	108.9 (2)
C4—C3—H3	118.7	C11—C12—H12A	109.5
C2—C3—H3	118.7	C11—C12—H12B	109.5
C3—C4—C10	119.0 (3)	H12A—C12—H12B	109.5
C3—C4—C1	119.4 (3)	C11—C12—H12C	109.5
C10—C4—C1	121.6 (3)	H12A—C12—H12C	109.5
C6—C5—C10	122.1 (3)	H12B—C12—H12C	109.5
C6—C5—H5	118.9	C11—C13—H13A	109.5
C10—C5—H5	118.9	C11—C13—H13B	109.4
C5—C6—C7	117.6 (3)	H13A—C13—H13B	109.5
C5—C6—C11	122.9 (3)	C11—C13—H13C	109.5
C7—C6—C11	119.6 (3)	H13A—C13—H13C	109.4
C8—C7—C6	121.4 (3)	H13B—C13—H13C	109.5
C8—C7—H7	119.3	C11—C14—H14A	109.5
C6—C7—H7	119.3	C11—C14—H14B	109.5
C9—C8—C7	119.4 (3)	H14A—C14—H14B	109.5
C9—C8—H8	120.3	C11—C14—H14C	109.5
C7—C8—H8	120.3	H14A—C14—H14C	109.5
C8—C9—O1	116.4 (2)	H14B—C14—H14C	109.5
C8—C9—C10	121.8 (3)	C2—O1—C9	121.59 (17)
O2—C2—C3—C4	−178.6 (3)	C6—C5—C10—C9	0.6 (4)
O1—C2—C3—C4	2.0 (4)	C6—C5—C10—C4	−179.9 (3)
C2—C3—C4—C10	1.1 (4)	C3—C4—C10—C9	−2.7 (4)
C2—C3—C4—C1	−178.1 (3)	C1—C4—C10—C9	176.5 (3)
Br1—C1—C4—C3	−102.3 (3)	C3—C4—C10—C5	177.8 (3)
Br1—C1—C4—C10	78.5 (3)	C1—C4—C10—C5	−3.0 (4)
C10—C5—C6—C7	−1.6 (4)	C5—C6—C11—C14	5.8 (4)
C10—C5—C6—C11	176.5 (3)	C7—C6—C11—C14	−176.1 (3)
C5—C6—C7—C8	1.4 (4)	C5—C6—C11—C13	126.0 (3)
C11—C6—C7—C8	−176.8 (3)	C7—C6—C11—C13	−55.9 (3)
C6—C7—C8—C9	−0.2 (5)	C5—C6—C11—C12	−114.7 (3)
C7—C8—C9—O1	179.2 (2)	C7—C6—C11—C12	63.4 (3)
C7—C8—C9—C10	−0.9 (5)	O2—C2—O1—C9	176.86 (19)
C8—C9—C10—C5	0.7 (4)	C3—C2—O1—C9	−3.7 (3)
O1—C9—C10—C5	−179.4 (2)	C8—C9—O1—C2	−177.8 (2)
C8—C9—C10—C4	−178.9 (3)	C10—C9—O1—C2	2.3 (4)
O1—C9—C10—C4	1.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2i	0.95	2.42	3.334 (4)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.95	2.42	3.334 (4)	162

Symmetry code: (i) .