3,6,8-Tribromo-7-ethyl-amino-4-methyl-2H-chromen-2-one.

In the title mol-ecule, C(12)H(10)Br(3)NO(2), the 2H-chromen ring is essentially planar (r.m.s. deviation = 0.022 Å) with the ethyl-amino group oriented at 13.9 (5)° with respect to the ring. The mol-ecular structure is stabilized by intra-molecular N-H⋯Br and C-H⋯Br interactions.

Related literature

For the synthetic procedure, see: Belluti et al. (2010 ▶). For a related structure, see: Kruszynski et al. (2005 ▶).

Experimental

Crystal data

C12H10Br3NO2

M = 439.94

Monoclinic,

a = 8.5045 (9) Å

b = 7.2551 (8) Å

c = 21.556 (2) Å

β = 94.720 (2)°

V = 1325.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 9.12 mm−1

T = 296 K

0.20 × 0.18 × 0.15 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.263, T max = 0.342

7355 measured reflections

2457 independent reflections

2002 reflections with I > 2σ(I)

R int = 0.034

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.099

S = 1.01

2457 reflections

169 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.63 e Å−3

Δρmin = −0.56 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985) ▶; cell refinement: CAD-4 Software ▶; data reduction: XCAD4 (Harms & Wocadlo,1995 ▶); 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812009221/pv2515sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009221/pv2515Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812009221/pv2515Isup3.cml

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

C12H10Br3NO2	F(000) = 840
Mr = 439.94	Dx = 2.205 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2620 reflections
a = 8.5045 (9) Å	θ = 2.4–25.5°
b = 7.2551 (8) Å	µ = 9.12 mm−1
c = 21.556 (2) Å	T = 296 K
β = 94.720 (2)°	BLOCK, colorless
V = 1325.5 (3) Å3	0.20 × 0.18 × 0.15 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	2002 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
Graphite monochromator	θmax = 25.5°, θmin = 1.9°
ω/2θ scans	h = −9→10
Absorption correction: ψ scan (North et al., 1968)	k = −8→8
Tmin = 0.263, Tmax = 0.342	l = −26→23
7355 measured reflections	3 standard reflections every 200 reflections
2457 independent reflections	intensity decay: 1%

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0605P)2 + 0.6207P] where P = (Fo2 + 2Fc2)/3
2457 reflections	(Δ/σ)max < 0.001
169 parameters	Δρmax = 0.63 e Å−3
1 restraint	Δρmin = −0.56 e Å−3

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.

	x	y	z	Uiso*/Ueq
Br1	0.35825 (6)	0.11548 (6)	0.05870 (2)	0.04316 (16)
Br2	0.41792 (7)	0.58281 (7)	−0.22380 (2)	0.05645 (19)
Br3	0.01975 (6)	0.79144 (7)	0.09690 (2)	0.05198 (18)
O1	0.3974 (3)	0.3023 (4)	−0.05962 (13)	0.0364 (7)
C8	0.1457 (5)	0.6305 (6)	0.0522 (2)	0.0354 (9)
C5	0.3144 (4)	0.4156 (5)	−0.02319 (19)	0.0313 (9)
C4	0.2630 (5)	0.5889 (5)	−0.0453 (2)	0.0335 (9)
C7	0.1975 (5)	0.4566 (6)	0.07545 (19)	0.0335 (9)
C2	0.3720 (5)	0.5264 (6)	−0.14159 (19)	0.0377 (10)
O2	0.5003 (4)	0.2360 (5)	−0.14659 (15)	0.0560 (9)
C9	0.1786 (5)	0.6931 (5)	−0.0049 (2)	0.0359 (9)
H9	0.1434	0.8097	−0.0174	0.043*
C1	0.4277 (5)	0.3477 (6)	−0.1195 (2)	0.0371 (10)
C3	0.2947 (5)	0.6444 (5)	−0.1069 (2)	0.0334 (9)
C6	0.2846 (5)	0.3532 (5)	0.03440 (19)	0.0314 (9)
N1	0.1665 (5)	0.3812 (6)	0.13117 (19)	0.0511 (11)
C10	0.2404 (6)	0.8311 (7)	−0.1302 (2)	0.0519 (12)
H10A	0.2757	0.8515	−0.1708	0.078*
H10B	0.2836	0.9243	−0.1021	0.078*
H10C	0.1273	0.8365	−0.1325	0.078*
C13	0.1232 (8)	0.4655 (9)	0.1875 (3)	0.0650 (15)
H13A	0.0167	0.5137	0.1812	0.078*
H13B	0.1938	0.5673	0.1986	0.078*
C14	0.1322 (8)	0.3266 (9)	0.2388 (2)	0.0668 (15)
H14A	0.0715	0.2198	0.2258	0.100*
H14B	0.0906	0.3791	0.2749	0.100*
H14C	0.2402	0.2916	0.2488	0.100*
H1	0.218 (6)	0.287 (5)	0.147 (2)	0.064 (18)*

	U11	U22	U33	U12	U13	U23
Br1	0.0588 (3)	0.0282 (2)	0.0433 (3)	0.00216 (19)	0.0097 (2)	0.00324 (18)
Br2	0.0814 (4)	0.0539 (3)	0.0367 (3)	0.0003 (3)	0.0208 (3)	0.0071 (2)
Br3	0.0578 (3)	0.0458 (3)	0.0550 (3)	0.0094 (2)	0.0203 (2)	−0.0111 (2)
O1	0.0488 (17)	0.0293 (15)	0.0323 (16)	0.0073 (13)	0.0110 (13)	0.0001 (12)
C8	0.039 (2)	0.033 (2)	0.034 (2)	0.0012 (18)	0.0082 (19)	−0.0109 (17)
C5	0.033 (2)	0.0264 (19)	0.035 (2)	−0.0005 (16)	0.0062 (18)	−0.0065 (17)
C4	0.038 (2)	0.028 (2)	0.035 (2)	−0.0015 (17)	0.0053 (18)	−0.0023 (17)
C7	0.035 (2)	0.036 (2)	0.030 (2)	−0.0066 (18)	0.0046 (17)	−0.0056 (18)
C2	0.049 (2)	0.037 (2)	0.028 (2)	−0.005 (2)	0.0055 (19)	0.0018 (18)
O2	0.083 (3)	0.0467 (19)	0.041 (2)	0.0135 (19)	0.0224 (19)	−0.0055 (16)
C9	0.041 (2)	0.025 (2)	0.042 (3)	0.0028 (17)	0.0050 (19)	−0.0048 (18)
C1	0.048 (2)	0.032 (2)	0.032 (2)	−0.0022 (19)	0.009 (2)	−0.0029 (18)
C3	0.040 (2)	0.027 (2)	0.034 (2)	−0.0009 (17)	0.0014 (18)	0.0025 (17)
C6	0.039 (2)	0.0244 (19)	0.031 (2)	−0.0015 (17)	0.0038 (18)	−0.0006 (16)
N1	0.071 (3)	0.048 (3)	0.037 (2)	0.004 (2)	0.017 (2)	0.0048 (18)
C10	0.065 (3)	0.040 (2)	0.051 (3)	0.015 (2)	0.011 (3)	0.014 (2)
C13	0.086 (4)	0.068 (4)	0.043 (3)	−0.006 (3)	0.020 (3)	−0.009 (3)
C14	0.089 (4)	0.079 (4)	0.034 (3)	−0.011 (3)	0.014 (3)	0.005 (3)

Br1—C6	1.894 (4)	O2—C1	1.200 (5)
Br2—C2	1.891 (4)	C9—H9	0.9300
Br3—C8	1.899 (4)	C3—C10	1.503 (6)
O1—C5	1.372 (5)	N1—C13	1.434 (6)
O1—C1	1.376 (5)	N1—H1	0.866 (10)
C8—C9	1.362 (6)	C10—H10A	0.9600
C8—C7	1.415 (6)	C10—H10B	0.9600
C5—C6	1.365 (6)	C10—H10C	0.9600
C5—C4	1.402 (6)	C13—C14	1.494 (8)
C4—C9	1.396 (6)	C13—H13A	0.9700
C4—C3	1.434 (6)	C13—H13B	0.9700
C7—N1	1.365 (6)	C14—H14A	0.9600
C7—C6	1.415 (6)	C14—H14B	0.9600
C2—C3	1.344 (6)	C14—H14C	0.9600
C2—C1	1.448 (6)
C5—O1—C1	122.5 (3)	C5—C6—C7	122.6 (4)
C9—C8—C7	122.4 (4)	C5—C6—Br1	118.1 (3)
C9—C8—Br3	114.8 (3)	C7—C6—Br1	119.2 (3)
C7—C8—Br3	122.8 (3)	C7—N1—C13	131.0 (4)
C6—C5—O1	117.7 (3)	C7—N1—H1	122 (4)
C6—C5—C4	122.0 (4)	C13—N1—H1	99 (4)
O1—C5—C4	120.3 (4)	C3—C10—H10A	109.5
C9—C4—C5	115.9 (4)	C3—C10—H10B	109.5
C9—C4—C3	124.8 (4)	H10A—C10—H10B	109.5
C5—C4—C3	119.3 (4)	C3—C10—H10C	109.5
N1—C7—C8	126.3 (4)	H10A—C10—H10C	109.5
N1—C7—C6	119.2 (4)	H10B—C10—H10C	109.5
C8—C7—C6	114.5 (4)	N1—C13—C14	109.8 (5)
C3—C2—C1	123.3 (4)	N1—C13—H13A	109.7
C3—C2—Br2	122.2 (3)	C14—C13—H13A	109.7
C1—C2—Br2	114.5 (3)	N1—C13—H13B	109.7
C8—C9—C4	122.5 (4)	C14—C13—H13B	109.7
C8—C9—H9	118.7	H13A—C13—H13B	108.2
C4—C9—H9	118.7	C13—C14—H14A	109.5
O2—C1—O1	116.0 (4)	C13—C14—H14B	109.5
O2—C1—C2	127.7 (4)	H14A—C14—H14B	109.5
O1—C1—C2	116.2 (4)	C13—C14—H14C	109.5
C2—C3—C4	118.3 (4)	H14A—C14—H14C	109.5
C2—C3—C10	122.6 (4)	H14B—C14—H14C	109.5
C4—C3—C10	119.1 (4)
C1—O1—C5—C6	176.9 (4)	C1—C2—C3—C4	−1.4 (6)
C1—O1—C5—C4	−3.0 (6)	Br2—C2—C3—C4	179.1 (3)
C6—C5—C4—C9	−0.4 (6)	C1—C2—C3—C10	178.8 (4)
O1—C5—C4—C9	179.6 (3)	Br2—C2—C3—C10	−0.7 (6)
C6—C5—C4—C3	−178.4 (4)	C9—C4—C3—C2	−177.2 (4)
O1—C5—C4—C3	1.5 (6)	C5—C4—C3—C2	0.6 (6)
C9—C8—C7—N1	−178.1 (4)	C9—C4—C3—C10	2.6 (7)
Br3—C8—C7—N1	−0.1 (6)	C5—C4—C3—C10	−179.5 (4)
C9—C8—C7—C6	−0.5 (6)	O1—C5—C6—C7	−178.7 (3)
Br3—C8—C7—C6	177.5 (3)	C4—C5—C6—C7	1.2 (6)
C7—C8—C9—C4	1.4 (7)	O1—C5—C6—Br1	−0.6 (5)
Br3—C8—C9—C4	−176.8 (3)	C4—C5—C6—Br1	179.3 (3)
C5—C4—C9—C8	−0.9 (6)	N1—C7—C6—C5	177.1 (4)
C3—C4—C9—C8	177.0 (4)	C8—C7—C6—C5	−0.7 (6)
C5—O1—C1—O2	−179.4 (4)	N1—C7—C6—Br1	−1.1 (5)
C5—O1—C1—C2	2.2 (6)	C8—C7—C6—Br1	−178.8 (3)
C3—C2—C1—O2	−178.2 (5)	C8—C7—N1—C13	−22.3 (9)
Br2—C2—C1—O2	1.4 (6)	C6—C7—N1—C13	160.2 (5)
C3—C2—C1—O1	0.0 (6)	C7—N1—C13—C14	−169.4 (5)
Br2—C2—C1—O1	179.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Br1	0.87 (1)	2.64 (4)	3.039 (4)	109 (3)
C10—H10A···Br2	0.96	2.60	3.176 (5)	118
C13—H13A···Br3	0.97	2.71	3.146 (7)	108

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Br1	0.87 (1)	2.64 (4)	3.039 (4)	109 (3)
C10—H10A⋯Br2	0.96	2.60	3.176 (5)	118
C13—H13A⋯Br3	0.97	2.71	3.146 (7)	108