2-Oxo-4-trifluoro-meth-yl-2H-chromen-7-yl 2-bromo-2-methyl-propano-ate.

In the title compound, C(14)H(10)BrF(3)O(4), the coumarin ring system is almost plannar (r.m.s. deviation = 0.025 Å) and a short C-H⋯F contact occurs. The propano-ate fragment is orientated almost perpendicular to the ring [dihedral angle = 71.80 (12)°]. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, generating [100] chains.

Related literature

For the applications of the title compound in polymer chemistry, see: Sinkel et al. (2008 ▶); Matyjaszewski et al. (2008 ▶); Stenzel-Rosenbaum et al. (2001 ▶).

Experimental

Crystal data

C14H10BrF3O4

M = 379.13

Triclinic,

a = 6.1842 (4) Å

b = 11.0297 (6) Å

c = 11.0619 (7) Å

α = 99.982 (2)°

β = 91.797 (2)°

γ = 104.387 (2)°

V = 717.61 (8) Å3

Z = 2

Mo Kα radiation

μ = 2.91 mm−1

T = 298 K

0.40 × 0.26 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.389, T max = 0.542

9951 measured reflections

3796 independent reflections

2390 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.109

S = 1.01

3796 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.78 e Å−3

Δρmin = −0.85 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020234/hb5450sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020234/hb5450Isup2.hkl

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

C14H10BrF3O4	Z = 2
Mr = 379.13	F(000) = 376
Triclinic, P1	Dx = 1.755 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.1842 (4) Å	Cell parameters from 3404 reflections
b = 11.0297 (6) Å	θ = 2.4–25.3°
c = 11.0619 (7) Å	µ = 2.91 mm−1
α = 99.982 (2)°	T = 298 K
β = 91.797 (2)°	Rectangular, colourless
γ = 104.387 (2)°	0.40 × 0.26 × 0.24 mm
V = 717.61 (8) Å3

Bruker APEXII CCD diffractometer	3796 independent reflections
Radiation source: fine-focus sealed tube	2390 reflections with I > 2σ(I)
graphite	Rint = 0.022
phi and ω scans	θmax = 30.8°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −7→8
Tmin = 0.389, Tmax = 0.542	k = −15→14
9951 measured reflections	l = −13→15

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0464P)2 + 0.448P] where P = (Fo2 + 2Fc2)/3
3796 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.78 e Å−3
0 restraints	Δρmin = −0.85 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 takeninto account individually in the estimation of esds in distances, anglesand torsion angles; correlations between esds in cell parameters are onlyused 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 > 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.

	x	y	z	Uiso*/Ueq
Br1	0.06908 (6)	−0.04175 (3)	0.29516 (4)	0.06662 (16)
C1	0.2614 (5)	0.5339 (3)	−0.2219 (3)	0.0450 (7)
C2	0.4147 (5)	0.4806 (3)	−0.2966 (3)	0.0450 (7)
H2	0.4574	0.5118	−0.3675	0.054*
C3	0.4972 (4)	0.3873 (3)	−0.2666 (2)	0.0363 (6)
C4	0.4377 (4)	0.3379 (2)	−0.1559 (2)	0.0322 (5)
C5	0.5183 (4)	0.2437 (3)	−0.1127 (2)	0.0375 (6)
H5	0.6232	0.2098	−0.1557	0.045*
C6	0.4449 (5)	0.2007 (3)	−0.0080 (3)	0.0408 (6)
H6	0.4995	0.1385	0.0202	0.049*
C7	0.2881 (4)	0.2518 (3)	0.0548 (2)	0.0359 (6)
C8	0.2074 (4)	0.3459 (3)	0.0179 (2)	0.0386 (6)
H8	0.1041	0.3801	0.0622	0.046*
C9	0.2849 (4)	0.3880 (2)	−0.0872 (2)	0.0333 (6)
C10	0.6453 (5)	0.3300 (3)	−0.3523 (3)	0.0464 (7)
C11	0.0108 (4)	0.1442 (3)	0.1690 (3)	0.0361 (6)
C12	−0.0307 (4)	0.1167 (3)	0.2974 (3)	0.0389 (6)
C13	0.1076 (6)	0.2198 (3)	0.4010 (3)	0.0541 (8)
H13A	0.2639	0.2317	0.3887	0.081*
H13B	0.0784	0.1940	0.4787	0.081*
H13C	0.0672	0.2983	0.4005	0.081*
C14	−0.2790 (5)	0.0855 (3)	0.3145 (3)	0.0516 (8)
H14A	−0.3331	0.1596	0.3129	0.077*
H14B	−0.3045	0.0591	0.3923	0.077*
H14C	−0.3569	0.0179	0.2493	0.077*
F1	0.6893 (4)	0.3893 (2)	−0.44723 (18)	0.0775 (6)
F2	0.8423 (3)	0.3353 (2)	−0.29621 (18)	0.0652 (5)
F3	0.5518 (3)	0.20819 (19)	−0.39741 (17)	0.0645 (5)
O1	0.2025 (3)	0.48421 (18)	−0.11926 (17)	0.0429 (5)
O2	0.1777 (4)	0.6161 (2)	−0.2441 (2)	0.0648 (6)
O3	0.2269 (3)	0.2130 (2)	0.16562 (17)	0.0452 (5)
O4	−0.1216 (3)	0.1118 (2)	0.08271 (19)	0.0498 (5)

	U11	U22	U33	U12	U13	U23
Br1	0.0781 (3)	0.0645 (3)	0.0835 (3)	0.04411 (19)	0.0312 (2)	0.0426 (2)
C1	0.0603 (18)	0.0383 (16)	0.0422 (16)	0.0201 (13)	0.0037 (14)	0.0123 (13)
C2	0.0613 (18)	0.0436 (17)	0.0361 (15)	0.0170 (13)	0.0083 (13)	0.0174 (13)
C3	0.0408 (14)	0.0373 (15)	0.0311 (13)	0.0087 (11)	0.0039 (11)	0.0083 (11)
C4	0.0354 (13)	0.0320 (13)	0.0301 (13)	0.0100 (10)	0.0012 (11)	0.0066 (11)
C5	0.0398 (14)	0.0386 (15)	0.0398 (15)	0.0179 (11)	0.0082 (12)	0.0103 (12)
C6	0.0420 (15)	0.0426 (16)	0.0436 (16)	0.0157 (12)	0.0015 (13)	0.0166 (13)
C7	0.0355 (13)	0.0419 (15)	0.0314 (13)	0.0071 (11)	0.0006 (11)	0.0141 (12)
C8	0.0399 (14)	0.0448 (16)	0.0359 (14)	0.0165 (12)	0.0090 (12)	0.0114 (12)
C9	0.0371 (13)	0.0322 (13)	0.0343 (14)	0.0136 (11)	−0.0003 (11)	0.0097 (11)
C10	0.0507 (17)	0.055 (2)	0.0388 (16)	0.0182 (14)	0.0111 (13)	0.0158 (14)
C11	0.0355 (13)	0.0387 (15)	0.0409 (15)	0.0163 (11)	0.0076 (12)	0.0150 (12)
C12	0.0410 (14)	0.0400 (15)	0.0434 (16)	0.0164 (12)	0.0110 (12)	0.0184 (13)
C13	0.063 (2)	0.062 (2)	0.0375 (16)	0.0097 (16)	0.0049 (14)	0.0203 (15)
C14	0.0483 (17)	0.0514 (18)	0.060 (2)	0.0164 (14)	0.0240 (15)	0.0162 (16)
F1	0.1027 (17)	0.1013 (16)	0.0556 (12)	0.0515 (13)	0.0434 (12)	0.0444 (12)
F2	0.0437 (10)	0.0907 (15)	0.0663 (12)	0.0224 (10)	0.0112 (9)	0.0201 (11)
F3	0.0773 (13)	0.0584 (12)	0.0548 (11)	0.0235 (10)	0.0128 (10)	−0.0077 (9)
O1	0.0573 (12)	0.0422 (11)	0.0403 (11)	0.0277 (9)	0.0093 (9)	0.0146 (9)
O2	0.0941 (18)	0.0559 (14)	0.0647 (15)	0.0455 (13)	0.0132 (13)	0.0270 (12)
O3	0.0371 (10)	0.0647 (13)	0.0372 (10)	0.0071 (9)	0.0029 (8)	0.0271 (9)
O4	0.0422 (11)	0.0607 (13)	0.0453 (12)	0.0078 (9)	−0.0033 (10)	0.0161 (10)

Br1—C12	1.990 (3)	C8—H8	0.9300
C1—O2	1.205 (3)	C9—O1	1.378 (3)
C1—O1	1.366 (3)	C10—F3	1.324 (4)
C1—C2	1.444 (4)	C10—F1	1.332 (3)
C2—C3	1.340 (4)	C10—F2	1.333 (4)
C2—H2	0.9300	C11—O4	1.181 (3)
C3—C4	1.447 (4)	C11—O3	1.368 (3)
C3—C10	1.507 (4)	C11—C12	1.520 (4)
C4—C9	1.391 (4)	C12—C14	1.513 (4)
C4—C5	1.404 (4)	C12—C13	1.529 (4)
C5—C6	1.375 (4)	C13—H13A	0.9600
C5—H5	0.9300	C13—H13B	0.9600
C6—C7	1.385 (4)	C13—H13C	0.9600
C6—H6	0.9300	C14—H14A	0.9600
C7—C8	1.373 (4)	C14—H14B	0.9600
C7—O3	1.400 (3)	C14—H14C	0.9600
C8—C9	1.382 (4)
O2—C1—O1	117.5 (3)	F3—C10—F2	106.4 (3)
O2—C1—C2	125.6 (3)	F1—C10—F2	106.6 (2)
O1—C1—C2	116.9 (2)	F3—C10—C3	111.5 (2)
C3—C2—C1	121.9 (3)	F1—C10—C3	112.1 (3)
C3—C2—H2	119.1	F2—C10—C3	112.4 (2)
C1—C2—H2	119.1	O4—C11—O3	123.6 (2)
C2—C3—C4	120.6 (3)	O4—C11—C12	126.0 (2)
C2—C3—C10	119.4 (3)	O3—C11—C12	110.4 (2)
C4—C3—C10	119.9 (2)	C14—C12—C11	110.2 (2)
C9—C4—C5	117.5 (2)	C14—C12—C13	112.9 (3)
C9—C4—C3	116.5 (2)	C11—C12—C13	114.2 (2)
C5—C4—C3	126.0 (2)	C14—C12—Br1	107.64 (19)
C6—C5—C4	121.1 (2)	C11—C12—Br1	102.84 (17)
C6—C5—H5	119.4	C13—C12—Br1	108.4 (2)
C4—C5—H5	119.4	C12—C13—H13A	109.5
C5—C6—C7	118.8 (2)	C12—C13—H13B	109.5
C5—C6—H6	120.6	H13A—C13—H13B	109.5
C7—C6—H6	120.6	C12—C13—H13C	109.5
C8—C7—C6	122.4 (2)	H13A—C13—H13C	109.5
C8—C7—O3	119.5 (2)	H13B—C13—H13C	109.5
C6—C7—O3	117.8 (2)	C12—C14—H14A	109.5
C7—C8—C9	117.7 (2)	C12—C14—H14B	109.5
C7—C8—H8	121.2	H14A—C14—H14B	109.5
C9—C8—H8	121.2	C12—C14—H14C	109.5
O1—C9—C8	115.6 (2)	H14A—C14—H14C	109.5
O1—C9—C4	121.9 (2)	H14B—C14—H14C	109.5
C8—C9—C4	122.5 (2)	C1—O1—C9	122.1 (2)
F3—C10—F1	107.5 (2)	C11—O3—C7	117.3 (2)
O2—C1—C2—C3	−178.7 (3)	C2—C3—C10—F3	−115.9 (3)
O1—C1—C2—C3	−0.5 (4)	C4—C3—C10—F3	61.5 (3)
C1—C2—C3—C4	−1.1 (4)	C2—C3—C10—F1	4.7 (4)
C1—C2—C3—C10	176.3 (3)	C4—C3—C10—F1	−177.9 (2)
C2—C3—C4—C9	2.8 (4)	C2—C3—C10—F2	124.8 (3)
C10—C3—C4—C9	−174.5 (2)	C4—C3—C10—F2	−57.8 (3)
C2—C3—C4—C5	−177.8 (3)	O4—C11—C12—C14	−20.7 (4)
C10—C3—C4—C5	4.8 (4)	O3—C11—C12—C14	159.3 (2)
C9—C4—C5—C6	1.5 (4)	O4—C11—C12—C13	−149.0 (3)
C3—C4—C5—C6	−177.9 (3)	O3—C11—C12—C13	31.0 (3)
C4—C5—C6—C7	0.2 (4)	O4—C11—C12—Br1	93.8 (3)
C5—C6—C7—C8	−1.6 (4)	O3—C11—C12—Br1	−86.2 (2)
C5—C6—C7—O3	−175.8 (2)	O2—C1—O1—C9	178.6 (3)
C6—C7—C8—C9	1.2 (4)	C2—C1—O1—C9	0.3 (4)
O3—C7—C8—C9	175.3 (2)	C8—C9—O1—C1	−178.9 (2)
C7—C8—C9—O1	−178.8 (2)	C4—C9—O1—C1	1.6 (4)
C7—C8—C9—C4	0.6 (4)	O4—C11—O3—C7	3.3 (4)
C5—C4—C9—O1	177.5 (2)	C12—C11—O3—C7	−176.7 (2)
C3—C4—C9—O1	−3.1 (4)	C8—C7—O3—C11	71.5 (3)
C5—C4—C9—C8	−1.9 (4)	C6—C7—O3—C11	−114.2 (3)
C3—C4—C9—C8	177.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···F2	0.93	2.47	3.019 (3)	118
C6—H6···O4i	0.93	2.52	3.261 (4)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯F2	0.93	2.47	3.019 (3)	118
C6—H6⋯O4i	0.93	2.52	3.261 (4)	136

Symmetry code: (i) .