1,4-Bis(4-bromo­but­oxy)benzene

The complete mol­ecule of the title compound, C₁₄H₂₀Br₂O₂, is generated by crystallographic inversion symmetry and the 4-bromo­but­oxy side chain adopts an extended conformation. In the crystal, weak C—H...π inter­actions are observed, which help to consolidate a herringbone packing motif.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.024
• wR factor = 0.052
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) .       1.11 Ratio
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          70 % Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Bruno et al., 2002); software used to prepare material for publication: publCIF (Westrip, 2010).

1,4-Bis(4-bromobutoxy)benzene

Crystal data

C14H20Br2O2	F(000) = 380
Mr = 380.12	Dx = 1.702 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.0845 (10) Å	Cell parameters from 3047 reflections
b = 5.3436 (5) Å	θ = 2.7–24.9°
c = 15.3509 (15) Å	µ = 5.46 mm^−1
β = 95.567 (4)°	T = 296 K
V = 741.68 (13) Å^3	Block, colourless
Z = 2	0.35 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer	1310 independent reflections
Radiation source: fine-focus sealed tube	1126 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
ω and φ scan	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −10→10
Tmin = 0.525, Tmax = 0.745	k = −6→6
7040 measured reflections	l = −18→18

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.024	H-atom parameters constrained
wR(F^2) = 0.052	w = 1/[σ^2(Fo^2) + (0.0214P)^2 + 0.4039P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
1310 reflections	Δρmax = 0.32 e Å^−3
82 parameters	Δρmin = −0.33 e Å^−3

Special details

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. H atoms were included in the refinement at calculated positions (C—H = 0.93–0.98 Å), with U_iso(H) = 1.2Ueq(C) using a riding-model approximation.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	−0.0397 (3)	1.4815 (5)	−0.34901 (18)	0.0487 (7)
H1A	−0.1220	1.5707	−0.3277	0.058*
H1B	−0.0796	1.3642	−0.3934	0.058*
C2	0.0404 (3)	1.3397 (4)	−0.27508 (15)	0.0354 (6)
H2A	0.0812	1.4561	−0.2306	0.043*
H2B	0.1216	1.2472	−0.2962	0.043*
C3	−0.0642 (3)	1.1585 (4)	−0.23511 (15)	0.0343 (6)
H3A	−0.1431	1.2523	−0.2119	0.041*
H3B	−0.1085	1.0478	−0.2804	0.041*
C4	0.0151 (3)	1.0047 (4)	−0.16294 (15)	0.0323 (5)
H4A	0.0974	0.9162	−0.1845	0.039*
H4B	0.0532	1.1121	−0.1150	0.039*
C5	−0.0386 (3)	0.6709 (4)	−0.06653 (14)	0.0288 (5)
C6	0.1050 (3)	0.6624 (4)	−0.02794 (15)	0.0305 (5)
H6	0.1759	0.7708	−0.0464	0.037*
C7	0.1431 (3)	0.4919 (4)	0.03832 (14)	0.0307 (5)
H7	0.2399	0.4864	0.0642	0.037*
O1	−0.08882 (18)	0.8306 (3)	−0.13368 (11)	0.0376 (4)
Br1	0.08821 (3)	1.72008 (5)	−0.40166 (2)	0.04831 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0408 (17)	0.0559 (16)	0.0491 (16)	−0.0108 (13)	0.0028 (13)	0.0206 (13)
C2	0.0386 (15)	0.0339 (12)	0.0338 (13)	−0.0018 (11)	0.0035 (11)	0.0026 (10)
C3	0.0347 (15)	0.0358 (13)	0.0324 (13)	−0.0015 (11)	0.0027 (11)	0.0056 (10)
C4	0.0335 (14)	0.0322 (12)	0.0314 (12)	−0.0024 (10)	0.0038 (11)	0.0037 (10)
C5	0.0323 (13)	0.0283 (11)	0.0256 (12)	0.0017 (10)	0.0021 (10)	0.0006 (9)
C6	0.0274 (13)	0.0322 (12)	0.0321 (12)	−0.0037 (10)	0.0035 (10)	0.0028 (10)
C7	0.0248 (13)	0.0353 (12)	0.0313 (12)	−0.0012 (10)	−0.0001 (10)	0.0015 (10)
O1	0.0323 (10)	0.0402 (9)	0.0390 (9)	−0.0043 (8)	−0.0022 (8)	0.0147 (8)
Br1	0.0566 (2)	0.04394 (17)	0.04603 (18)	−0.00749 (13)	0.01338 (13)	0.01054 (12)

Geometric parameters (Å, º)

C1—C2	1.494 (3)	C4—O1	1.428 (3)
C1—Br1	1.952 (2)	C4—H4A	0.9700
C1—H1A	0.9700	C4—H4B	0.9700
C1—H1B	0.9700	C5—C6	1.381 (3)
C2—C3	1.526 (3)	C5—O1	1.381 (3)
C2—H2A	0.9700	C5—C7^i	1.387 (3)
C2—H2B	0.9700	C6—C7	1.384 (3)
C3—C4	1.506 (3)	C6—H6	0.9300
C3—H3A	0.9700	C7—C5^i	1.387 (3)
C3—H3B	0.9700	C7—H7	0.9300
C2—C1—Br1	112.34 (19)	H3A—C3—H3B	107.9
C2—C1—H1A	109.1	O1—C4—C3	107.66 (19)
Br1—C1—H1A	109.1	O1—C4—H4A	110.2
C2—C1—H1B	109.1	C3—C4—H4A	110.2
Br1—C1—H1B	109.1	O1—C4—H4B	110.2
H1A—C1—H1B	107.9	C3—C4—H4B	110.2
C1—C2—C3	110.6 (2)	H4A—C4—H4B	108.5
C1—C2—H2A	109.5	C6—C5—O1	124.8 (2)
C3—C2—H2A	109.5	C6—C5—C7^i	119.5 (2)
C1—C2—H2B	109.5	O1—C5—C7^i	115.7 (2)
C3—C2—H2B	109.5	C5—C6—C7	119.7 (2)
H2A—C2—H2B	108.1	C5—C6—H6	120.2
C4—C3—C2	111.7 (2)	C7—C6—H6	120.2
C4—C3—H3A	109.3	C6—C7—C5^i	120.8 (2)
C2—C3—H3A	109.3	C6—C7—H7	119.6
C4—C3—H3B	109.3	C5^i—C7—H7	119.6
C2—C3—H3B	109.3	C5—O1—C4	117.18 (18)
Br1—C1—C2—C3	179.19 (17)	C5—C6—C7—C5^i	0.0 (4)
C1—C2—C3—C4	177.5 (2)	C6—C5—O1—C4	−2.2 (3)
C2—C3—C4—O1	−176.29 (18)	C7^i—C5—O1—C4	178.59 (18)
O1—C5—C6—C7	−179.2 (2)	C3—C4—O1—C5	−179.55 (19)
C7^i—C5—C6—C7	0.0 (4)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···Cg1^ii	0.97	2.84	3.664 (3)	144

Symmetry code: (ii) x−1/2, −y−1/2, z−3/2.