Crystal structure of 4-bromo-phenyl-2-oxo-2H-chromene-3-carboxyl-ate.

In the title compound, C16H9BrO4, the coumarin ring system is approximately planar, with an r.m.s deviation of the ten fitted non-H atoms of 0.031 Å, and forms a dihedral angle of 25.85 (10)° with the bromo-benzene ring. The carbonyl atoms are syn. In the crystal, mol-ecules are connected along [001] via C-H⋯O inter-actions, forming C(6) chains. Neighbouring C(6) chains are connected via several π-π inter-actions [range of centroid-centroid distances = 3.7254 (15)-3.7716 (16) Å], leading to sheets propagating in the bc plane.

Related literature

For related structures, see: Sreenivasa et al. (2013 ▸); Palakshamurthy, Sreenivasa et al. (2013 ▸); Palakshamurthy, Devarajegowda et al. (2013 ▸); Devarajegowda et al. (2013 ▸). For the biological activity and other applications of 2-oxo-2H-chromene derivatives, see: Abdel-Aziz et al. (2013 ▸); Kostova (2006 ▸); Chandrasekharan & Kelly (2002 ▸).

Experimental

Crystal data

C16H9BrO4

M = 345.14

Monoclinic,

a = 16.0782 (10) Å

b = 7.2618 (4) Å

c = 12.7396 (8) Å

β = 113.311 (4)°

V = 1366.01 (15) Å3

Z = 4

Mo Kα radiation

μ = 3.02 mm−1

T = 296 K

0.24 × 0.18 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▸) T min = 0.526, T max = 0.617

20483 measured reflections

2395 independent reflections

1831 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.079

S = 1.01

2395 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.54 e Å−3

Data collection: APEX2 (Bruker, 2013 ▸); cell refinement: SAINT (Bruker, 2013 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: SHELXL2014.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015006738/tk5362sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015006738/tk5362Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015006738/tk5362Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015006738/tk5362fig1.tif

The mol­ecular structure of the title compound, showing the atom labelling and displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.

via . DOI: 10.1107/S2056989015006738/tk5362fig2.tif

The crystal packing of the title compound via C—H⋯O inter­actions along [001]. Hydrogen bonds are shown as dashed lines.

Click here for additional data file.

. DOI: 10.1107/S2056989015006738/tk5362fig3.tif

Various π–π inter­actions observed in the crystal packing

CCDC reference: 1057743

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H9BrO4	Prism
Mr = 345.14	Dx = 1.678 Mg m−3
Monoclinic, P21/c	Melting point: 523 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 16.0782 (10) Å	Cell parameters from 2395 reflections
b = 7.2618 (4) Å	θ = 2.8–25.0°
c = 12.7396 (8) Å	µ = 3.02 mm−1
β = 113.311 (4)°	T = 296 K
V = 1366.01 (15) Å3	Prism, colourless
Z = 4	0.24 × 0.18 × 0.16 mm
F(000) = 688

Bruker APEXII CCD diffractometer	2395 independent reflections
Radiation source: fine-focus sealed tube	1831 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
Detector resolution: 2.01 pixels mm-1	θmax = 25.0°, θmin = 2.8°
φ and ω scans	h = −19→19
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −8→8
Tmin = 0.526, Tmax = 0.617	l = −15→15
20483 measured reflections

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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.079	w = 1/[σ2(Fo2) + (0.0319P)2 + 0.8274P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
2395 reflections	Δρmax = 0.45 e Å−3
191 parameters	Δρmin = −0.54 e Å−3
0 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.0062 (6)
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
Br1	0.94359 (2)	0.14526 (6)	0.64830 (3)	0.0907 (2)
O1	0.31144 (12)	0.1686 (2)	−0.06316 (14)	0.0517 (5)
O2	0.44603 (13)	0.1964 (3)	−0.06745 (15)	0.0612 (5)
O3	0.58965 (12)	0.2657 (3)	0.15291 (14)	0.0556 (5)
O4	0.56890 (11)	0.0734 (2)	0.27929 (13)	0.0428 (4)
C1	0.25543 (17)	0.1424 (3)	−0.0061 (2)	0.0460 (6)
C2	0.1631 (2)	0.1504 (4)	−0.0694 (3)	0.0613 (8)
H2	0.1403	0.1720	−0.1477	0.074*
C3	0.1059 (2)	0.1257 (4)	−0.0142 (3)	0.0709 (9)
H3	0.0436	0.1322	−0.0558	0.085*
C4	0.1389 (2)	0.0915 (4)	0.1017 (3)	0.0673 (9)
H4	0.0990	0.0734	0.1372	0.081*
C5	0.23074 (18)	0.0840 (4)	0.1648 (3)	0.0547 (7)
H5	0.2530	0.0613	0.2429	0.066*
C6	0.29078 (17)	0.1108 (3)	0.1108 (2)	0.0413 (6)
C7	0.38706 (16)	0.1145 (3)	0.1709 (2)	0.0394 (6)
H7	0.4122	0.0939	0.2493	0.047*
C8	0.44200 (16)	0.1472 (3)	0.11609 (19)	0.0364 (6)
C9	0.40485 (18)	0.1736 (3)	−0.0079 (2)	0.0440 (6)
C10	0.54071 (17)	0.1702 (3)	0.18007 (19)	0.0385 (6)
C11	0.65769 (16)	0.0988 (3)	0.36007 (19)	0.0370 (5)
C12	0.66608 (17)	0.1487 (3)	0.4677 (2)	0.0433 (6)
H12	0.6149	0.1711	0.4827	0.052*
C13	0.75178 (19)	0.1654 (4)	0.5536 (2)	0.0517 (7)
H13	0.7590	0.2000	0.6270	0.062*
C14	0.82608 (18)	0.1301 (4)	0.5288 (2)	0.0499 (7)
C15	0.81735 (18)	0.0805 (4)	0.4214 (2)	0.0538 (7)
H15	0.8686	0.0581	0.4065	0.065*
C16	0.73210 (17)	0.0637 (4)	0.3352 (2)	0.0452 (6)
H16	0.7251	0.0293	0.2619	0.054*

	U11	U22	U33	U12	U13	U23
Br1	0.0491 (2)	0.1081 (3)	0.0795 (3)	−0.01632 (19)	−0.01221 (17)	0.0173 (2)
O1	0.0460 (11)	0.0681 (12)	0.0343 (9)	0.0056 (9)	0.0087 (8)	−0.0015 (8)
O2	0.0622 (13)	0.0888 (15)	0.0368 (10)	0.0067 (11)	0.0240 (10)	0.0059 (10)
O3	0.0497 (11)	0.0724 (13)	0.0443 (10)	−0.0097 (10)	0.0181 (9)	0.0127 (9)
O4	0.0364 (9)	0.0547 (10)	0.0336 (9)	−0.0038 (8)	0.0100 (7)	0.0081 (8)
C1	0.0401 (15)	0.0421 (15)	0.0489 (15)	0.0008 (11)	0.0102 (13)	−0.0059 (12)
C2	0.0473 (18)	0.0615 (19)	0.0576 (18)	0.0004 (14)	0.0020 (15)	−0.0034 (14)
C3	0.0383 (17)	0.064 (2)	0.096 (3)	−0.0063 (14)	0.0115 (18)	−0.0058 (18)
C4	0.0465 (18)	0.064 (2)	0.094 (3)	−0.0078 (15)	0.0305 (18)	−0.0008 (18)
C5	0.0470 (17)	0.0564 (17)	0.0636 (17)	−0.0055 (14)	0.0250 (15)	0.0011 (14)
C6	0.0403 (14)	0.0363 (14)	0.0455 (14)	0.0000 (11)	0.0150 (12)	−0.0028 (11)
C7	0.0421 (14)	0.0375 (13)	0.0367 (13)	0.0018 (11)	0.0135 (11)	−0.0006 (10)
C8	0.0421 (14)	0.0352 (13)	0.0316 (12)	0.0027 (10)	0.0144 (11)	−0.0010 (10)
C9	0.0464 (15)	0.0485 (15)	0.0335 (13)	0.0059 (12)	0.0121 (12)	−0.0013 (11)
C10	0.0433 (14)	0.0409 (14)	0.0336 (13)	0.0007 (11)	0.0178 (11)	−0.0006 (10)
C11	0.0333 (13)	0.0405 (13)	0.0354 (12)	−0.0006 (11)	0.0117 (10)	0.0040 (10)
C12	0.0401 (15)	0.0506 (15)	0.0407 (14)	0.0037 (12)	0.0177 (12)	0.0031 (11)
C13	0.0576 (18)	0.0535 (16)	0.0374 (14)	−0.0025 (13)	0.0120 (13)	0.0006 (12)
C14	0.0381 (15)	0.0502 (16)	0.0487 (16)	−0.0054 (12)	0.0036 (12)	0.0084 (12)
C15	0.0375 (15)	0.0610 (17)	0.0630 (18)	0.0030 (13)	0.0200 (14)	0.0106 (14)
C16	0.0445 (15)	0.0535 (16)	0.0399 (13)	0.0011 (12)	0.0192 (12)	0.0023 (12)

Br1—C14	1.903 (3)	C5—H5	0.9300
O1—C1	1.376 (3)	C6—C7	1.430 (3)
O1—C9	1.384 (3)	C7—C8	1.346 (3)
O2—C9	1.200 (3)	C7—H7	0.9300
O3—C10	1.198 (3)	C8—C9	1.463 (3)
O4—C10	1.358 (3)	C8—C10	1.479 (3)
O4—C11	1.403 (3)	C11—C12	1.372 (3)
C1—C2	1.382 (4)	C11—C16	1.377 (3)
C1—C6	1.387 (4)	C12—C13	1.385 (4)
C2—C3	1.373 (5)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.375 (4)
C3—C4	1.380 (5)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.368 (4)
C4—C5	1.374 (4)	C15—C16	1.381 (4)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.402 (4)	C16—H16	0.9300
C1—O1—C9	122.67 (19)	C9—C8—C10	118.1 (2)
C10—O4—C11	118.88 (18)	O2—C9—O1	116.2 (2)
O1—C1—C2	117.5 (2)	O2—C9—C8	127.5 (2)
O1—C1—C6	121.0 (2)	O1—C9—C8	116.3 (2)
C2—C1—C6	121.5 (3)	O3—C10—O4	123.6 (2)
C3—C2—C1	118.6 (3)	O3—C10—C8	126.2 (2)
C3—C2—H2	120.7	O4—C10—C8	110.2 (2)
C1—C2—H2	120.7	C12—C11—C16	121.9 (2)
C2—C3—C4	121.3 (3)	C12—C11—O4	115.9 (2)
C2—C3—H3	119.4	C16—C11—O4	122.1 (2)
C4—C3—H3	119.4	C11—C12—C13	119.1 (2)
C5—C4—C3	120.2 (3)	C11—C12—H12	120.4
C5—C4—H4	119.9	C13—C12—H12	120.4
C3—C4—H4	119.9	C14—C13—C12	119.0 (2)
C4—C5—C6	119.8 (3)	C14—C13—H13	120.5
C4—C5—H5	120.1	C12—C13—H13	120.5
C6—C5—H5	120.1	C15—C14—C13	121.6 (2)
C1—C6—C5	118.7 (2)	C15—C14—Br1	119.5 (2)
C1—C6—C7	117.9 (2)	C13—C14—Br1	118.9 (2)
C5—C6—C7	123.3 (2)	C14—C15—C16	119.7 (2)
C8—C7—C6	121.3 (2)	C14—C15—H15	120.2
C8—C7—H7	119.4	C16—C15—H15	120.2
C6—C7—H7	119.4	C11—C16—C15	118.7 (2)
C7—C8—C9	120.8 (2)	C11—C16—H16	120.7
C7—C8—C10	121.0 (2)	C15—C16—H16	120.7
C9—O1—C1—C2	176.4 (2)	C7—C8—C9—O1	2.0 (3)
C9—O1—C1—C6	−3.1 (4)	C10—C8—C9—O1	−173.9 (2)
O1—C1—C2—C3	−179.7 (2)	C11—O4—C10—O3	6.3 (3)
C6—C1—C2—C3	−0.2 (4)	C11—O4—C10—C8	−170.71 (19)
C1—C2—C3—C4	−0.7 (4)	C7—C8—C10—O3	−148.3 (3)
C2—C3—C4—C5	0.9 (5)	C9—C8—C10—O3	27.6 (4)
C3—C4—C5—C6	−0.2 (4)	C7—C8—C10—O4	28.7 (3)
O1—C1—C6—C5	−179.7 (2)	C9—C8—C10—O4	−155.5 (2)
C2—C1—C6—C5	0.9 (4)	C10—O4—C11—C12	124.6 (2)
O1—C1—C6—C7	2.8 (3)	C10—O4—C11—C16	−59.7 (3)
C2—C1—C6—C7	−176.7 (2)	C16—C11—C12—C13	0.4 (4)
C4—C5—C6—C1	−0.7 (4)	O4—C11—C12—C13	176.2 (2)
C4—C5—C6—C7	176.7 (3)	C11—C12—C13—C14	−0.5 (4)
C1—C6—C7—C8	−0.1 (3)	C12—C13—C14—C15	0.5 (4)
C5—C6—C7—C8	−177.6 (2)	C12—C13—C14—Br1	−177.94 (19)
C6—C7—C8—C9	−2.2 (3)	C13—C14—C15—C16	−0.5 (4)
C6—C7—C8—C10	173.5 (2)	Br1—C14—C15—C16	178.0 (2)
C1—O1—C9—O2	179.7 (2)	C12—C11—C16—C15	−0.3 (4)
C1—O1—C9—C8	0.7 (3)	O4—C11—C16—C15	−175.9 (2)
C7—C8—C9—O2	−176.9 (3)	C14—C15—C16—C11	0.4 (4)
C10—C8—C9—O2	7.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O3i	0.93	2.40	3.124 (3)	134

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C12H12O3i	0.93	2.40	3.124(3)	134

Symmetry code: (i) .