2,2,6,6-Tetra-bromo-3,4,4,5-tetra-meth-oxy-cyclo-hexa-none.

In the title compound, C10H14Br4O5, synthesized from the meth-oxy Schiff base N-(pyridin-2-ylmeth-yl)meth-oxy-aniline and mol-ecular bromine, the cyclo-hexa-none ring has a chair conformation with one of the four meth-oxy groups equatorially orientated with respect to the carbonyl group and the others axially orientated. The C-Br bond lengthsvary from 1.942 (4) to1.964 (4) Å. In the crystal, weak C-H⋯Ocarbon-yl hydrogen-bonding inter-actions generate chains extending along the b-axis direction. Also present in the structure are two short inter-molecular Br⋯Ometh-oxy inter-actions [3.020 (3) and 3.073 (4) Å].

Related literature

For the synthesis and applications of 2,2,6,6-tetra­bromo-3,4,4, 5-tetra­meth­oxy­cyclo­hexa­none and related structures, see: Khan et al. (2004 ▶). For applications of brominated compounds, see: Alaee (2003 ▶); Czerski & Szymanska (2005 ▶); Cupples et al. (2005 ▶).

Experimental

Crystal data

C10H14Br4O5

M = 533.81

Monoclinic,

a = 10.396 (5) Å

b = 12.441 (5) Å

c = 12.316 (5) Å

β = 105.502 (5)°

V = 1535.0 (11) Å3

Z = 4

Mo Kα radiation

μ = 10.50 mm−1

T = 100 K

0.20 × 0.15 × 0.12 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.228, T max = 0.366

20265 measured reflections

2867 independent reflections

2466 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.086

S = 1.05

2867 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.85 e Å−3

Δρmin = −1.01 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenberg & Putz, 2006 ▶); software used to prepare material for publication: DIAMOND.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681401472X/zs2305sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681401472X/zs2305Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681401472X/zs2305Isup3.cml

CCDC reference: 1009490

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

C10H14Br4O5	F(000) = 1016
Mr = 533.81	Dx = 2.310 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 999 reflections
a = 10.396 (5) Å	θ = 2.6–28.6°
b = 12.441 (5) Å	µ = 10.50 mm−1
c = 12.316 (5) Å	T = 100 K
β = 105.502 (5)°	Block, yellow
V = 1535.0 (11) Å3	0.20 × 0.15 × 0.12 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2867 independent reflections
Radiation source: fine-focus sealed tube	2466 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
ω scans	θmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −12→12
Tmin = 0.228, Tmax = 0.366	k = −15→15
20265 measured reflections	l = −14→14

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0476P)2 + 1.8635P] where P = (Fo2 + 2Fc2)/3
2867 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.85 e Å−3
0 restraints	Δρmin = −1.01 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 > 2sigma(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	0.6442 (4)	0.0403 (3)	0.2171 (3)	0.0253 (8)
C2	0.7031 (4)	0.1525 (3)	0.2524 (3)	0.0244 (8)
C3	0.6061 (4)	0.2460 (3)	0.2078 (3)	0.0236 (8)
H3	0.6444	0.3136	0.2429	0.028*
C4	0.4661 (4)	0.2290 (3)	0.2259 (3)	0.0253 (8)
C5	0.4051 (4)	0.1254 (3)	0.1655 (3)	0.0231 (8)
H5	0.3972	0.1352	0.0850	0.028*
C6	0.4933 (4)	0.0256 (3)	0.2045 (3)	0.0245 (8)
C7	0.6279 (5)	0.3481 (3)	0.0472 (4)	0.0381 (11)
H7A	0.6112	0.3431	−0.0331	0.057*
H7B	0.7215	0.3594	0.0805	0.057*
H7C	0.5784	0.4073	0.0657	0.057*
C8	0.3675 (5)	0.2322 (5)	0.3844 (4)	0.0517 (14)
H8A	0.3942	0.2343	0.4652	0.078*
H8B	0.3162	0.1683	0.3597	0.078*
H8C	0.3141	0.2943	0.3561	0.078*
C9	0.4060 (5)	0.4176 (4)	0.2142 (5)	0.0489 (13)
H9A	0.3407	0.4663	0.1706	0.073*
H9B	0.4933	0.4387	0.2097	0.073*
H9C	0.4029	0.4193	0.2914	0.073*
C10	0.1701 (5)	0.1231 (5)	0.0796 (5)	0.0619 (17)
H10A	0.0869	0.1052	0.0951	0.093*
H10B	0.1814	0.0800	0.0182	0.093*
H10C	0.1699	0.1978	0.0599	0.093*
O1	0.7121 (3)	−0.0326 (2)	0.2003 (3)	0.0409 (8)
O2	0.5874 (3)	0.2513 (2)	0.0895 (2)	0.0273 (6)
O3	0.3779 (3)	0.3107 (2)	0.1706 (3)	0.0322 (7)
O4	0.4841 (3)	0.2319 (3)	0.3426 (2)	0.0336 (7)
O5	0.2763 (3)	0.1030 (2)	0.1766 (3)	0.0346 (7)
Br1	0.76975 (4)	0.15408 (4)	0.41548 (4)	0.03859 (15)
Br2	0.86086 (4)	0.16954 (4)	0.19556 (5)	0.04340 (15)
Br3	0.48249 (5)	−0.02879 (4)	0.35148 (4)	0.03964 (15)
Br4	0.42888 (5)	−0.08868 (3)	0.09570 (4)	0.03854 (14)

	U11	U22	U33	U12	U13	U23
C1	0.028 (2)	0.028 (2)	0.0225 (19)	0.0045 (17)	0.0103 (16)	0.0020 (16)
C2	0.0189 (19)	0.031 (2)	0.026 (2)	0.0010 (15)	0.0107 (16)	−0.0048 (16)
C3	0.0242 (19)	0.0233 (19)	0.0241 (19)	−0.0026 (15)	0.0077 (16)	−0.0036 (15)
C4	0.0220 (19)	0.032 (2)	0.0231 (19)	0.0070 (16)	0.0088 (16)	−0.0032 (17)
C5	0.0210 (19)	0.029 (2)	0.0227 (19)	−0.0029 (16)	0.0120 (16)	0.0013 (16)
C6	0.028 (2)	0.026 (2)	0.0216 (18)	0.0004 (16)	0.0100 (16)	0.0013 (15)
C7	0.042 (3)	0.034 (2)	0.040 (3)	−0.0062 (19)	0.014 (2)	0.004 (2)
C8	0.044 (3)	0.079 (4)	0.041 (3)	0.012 (3)	0.028 (2)	−0.008 (3)
C9	0.051 (3)	0.031 (3)	0.065 (3)	0.013 (2)	0.016 (3)	−0.014 (2)
C10	0.020 (2)	0.092 (4)	0.067 (4)	−0.012 (3)	−0.001 (2)	0.032 (3)
O1	0.0357 (17)	0.0313 (17)	0.058 (2)	0.0098 (13)	0.0158 (15)	−0.0045 (15)
O2	0.0300 (15)	0.0288 (15)	0.0262 (14)	−0.0063 (12)	0.0129 (12)	−0.0037 (11)
O3	0.0279 (15)	0.0296 (15)	0.0391 (16)	0.0100 (12)	0.0092 (13)	−0.0027 (13)
O4	0.0319 (16)	0.0483 (18)	0.0256 (15)	0.0072 (13)	0.0161 (13)	−0.0052 (13)
O5	0.0206 (14)	0.0475 (19)	0.0388 (17)	−0.0042 (12)	0.0134 (13)	0.0066 (14)
Br1	0.0321 (2)	0.0495 (3)	0.0289 (2)	0.00714 (19)	−0.00106 (18)	−0.00593 (19)
Br2	0.0262 (2)	0.0488 (3)	0.0627 (3)	0.00206 (18)	0.0249 (2)	0.0017 (2)
Br3	0.0440 (3)	0.0459 (3)	0.0336 (2)	0.0030 (2)	0.0184 (2)	0.0132 (2)
Br4	0.0484 (3)	0.0277 (2)	0.0401 (3)	−0.01180 (18)	0.0127 (2)	−0.00577 (18)

C1—O1	1.201 (5)	C7—O2	1.420 (5)
C1—C2	1.540 (6)	C7—H7A	0.9600
C1—C6	1.545 (5)	C7—H7B	0.9600
C2—C3	1.540 (5)	C7—H7C	0.9600
C2—Br1	1.942 (4)	C8—O4	1.439 (5)
C2—Br2	1.959 (4)	C8—H8A	0.9600
C3—O2	1.419 (5)	C8—H8B	0.9600
C3—C4	1.545 (5)	C8—H8C	0.9600
C3—H3	0.9800	C9—O3	1.434 (5)
C4—O4	1.399 (5)	C9—H9A	0.9600
C4—O3	1.416 (5)	C9—H9B	0.9600
C4—C5	1.537 (6)	C9—H9C	0.9600
C5—O5	1.410 (5)	C10—O5	1.415 (6)
C5—C6	1.542 (5)	C10—H10A	0.9600
C5—H5	0.9800	C10—H10B	0.9600
C6—Br4	1.946 (4)	C10—H10C	0.9600
C6—Br3	1.964 (4)
O1—C1—C2	121.7 (4)	C1—C6—Br3	104.8 (2)
O1—C1—C6	121.4 (4)	Br4—C6—Br3	106.80 (19)
C2—C1—C6	116.9 (3)	O2—C7—H7A	109.5
C1—C2—C3	114.2 (3)	O2—C7—H7B	109.5
C1—C2—Br1	107.8 (3)	H7A—C7—H7B	109.5
C3—C2—Br1	112.3 (3)	O2—C7—H7C	109.5
C1—C2—Br2	107.7 (3)	H7A—C7—H7C	109.5
C3—C2—Br2	108.8 (3)	H7B—C7—H7C	109.5
Br1—C2—Br2	105.50 (18)	O4—C8—H8A	109.5
O2—C3—C2	107.3 (3)	O4—C8—H8B	109.5
O2—C3—C4	106.2 (3)	H8A—C8—H8B	109.5
C2—C3—C4	113.4 (3)	O4—C8—H8C	109.5
O2—C3—H3	109.9	H8A—C8—H8C	109.5
C2—C3—H3	109.9	H8B—C8—H8C	109.5
C4—C3—H3	109.9	O3—C9—H9A	109.5
O4—C4—O3	111.5 (3)	O3—C9—H9B	109.5
O4—C4—C5	116.4 (3)	H9A—C9—H9B	109.5
O3—C4—C5	103.8 (3)	O3—C9—H9C	109.5
O4—C4—C3	105.8 (3)	H9A—C9—H9C	109.5
O3—C4—C3	110.2 (3)	H9B—C9—H9C	109.5
C5—C4—C3	109.1 (3)	O5—C10—H10A	109.5
O5—C5—C4	113.5 (3)	O5—C10—H10B	109.5
O5—C5—C6	108.2 (3)	H10A—C10—H10B	109.5
C4—C5—C6	112.9 (3)	O5—C10—H10C	109.5
O5—C5—H5	107.3	H10A—C10—H10C	109.5
C4—C5—H5	107.3	H10B—C10—H10C	109.5
C6—C5—H5	107.3	C3—O2—C7	116.3 (3)
C5—C6—C1	116.0 (3)	C4—O3—C9	116.4 (3)
C5—C6—Br4	107.9 (2)	C4—O4—C8	118.2 (3)
C1—C6—Br4	108.0 (3)	C5—O5—C10	115.5 (3)
C5—C6—Br3	112.9 (3)
O1—C1—C2—C3	147.2 (4)	C3—C4—C5—C6	56.7 (4)
C6—C1—C2—C3	−33.0 (5)	O5—C5—C6—C1	−170.4 (3)
O1—C1—C2—Br1	−87.3 (4)	C4—C5—C6—C1	−44.0 (4)
C6—C1—C2—Br1	92.6 (3)	O5—C5—C6—Br4	68.3 (3)
O1—C1—C2—Br2	26.2 (5)	C4—C5—C6—Br4	−165.3 (3)
C6—C1—C2—Br2	−154.0 (3)	O5—C5—C6—Br3	−49.5 (4)
C1—C2—C3—O2	−69.5 (4)	C4—C5—C6—Br3	77.0 (3)
Br1—C2—C3—O2	167.3 (2)	O1—C1—C6—C5	−148.5 (4)
Br2—C2—C3—O2	50.9 (3)	C2—C1—C6—C5	31.7 (5)
C1—C2—C3—C4	47.5 (4)	O1—C1—C6—Br4	−27.3 (4)
Br1—C2—C3—C4	−75.7 (3)	C2—C1—C6—Br4	152.9 (3)
Br2—C2—C3—C4	167.9 (2)	O1—C1—C6—Br3	86.3 (4)
O2—C3—C4—O4	−175.7 (3)	C2—C1—C6—Br3	−93.5 (3)
C2—C3—C4—O4	66.7 (4)	C2—C3—O2—C7	−118.5 (4)
O2—C3—C4—O3	−55.0 (4)	C4—C3—O2—C7	119.9 (4)
C2—C3—C4—O3	−172.6 (3)	O4—C4—O3—C9	50.5 (5)
O2—C3—C4—C5	58.4 (4)	C5—C4—O3—C9	176.6 (4)
C2—C3—C4—C5	−59.2 (4)	C3—C4—O3—C9	−66.7 (5)
O4—C4—C5—O5	60.8 (4)	O3—C4—O4—C8	52.1 (5)
O3—C4—C5—O5	−62.2 (4)	C5—C4—O4—C8	−66.7 (5)
C3—C4—C5—O5	−179.7 (3)	C3—C4—O4—C8	172.0 (4)
O4—C4—C5—C6	−62.8 (4)	C4—C5—O5—C10	105.2 (5)
O3—C4—C5—C6	174.3 (3)	C6—C5—O5—C10	−128.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1i	0.98	2.41	3.361 (5)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1i	0.98	2.41	3.361 (5)	163

Symmetry code: (i) .