


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808028730/si2104sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808028730/si2104Isup2.hkl |
CCDC reference: 706063
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.026
- wR factor = 0.064
- Data-to-parameter ratio = 18.0
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.391 0.764 Tmin and Tmax expected: 0.331 0.750 RR = 1.159 Please check that your absorption correction is appropriate. PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.06 PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. Br1 .. 3.41 Ang. PLAT060_ALERT_4_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.17 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 200 Deg.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was prepared as described in literature (Maruyama & Kawanishi 2002) and recrystallized from dichloromethane-ethanol at room temperature to give the desired crystals suitable for single-crystal X-ray diffraction.
H atoms attached to C atoms of the title compound were placed in geometrically idealized positions and treated as riding with C—H distances constrained to 0.93 (aromatic CH), or 0.96 Å (methyl CH3), and 0.97 Å (methylene CH2) and constrained to ride on their parent atoms, with Uĩso~(H) = 1.2Ueq(C)(1.5Ueq for methyl H).
Data collection: SMART (Bruker, 2004); cell refinement: SMART (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).
C18H28Br2O2 | Z = 1 |
Mr = 436.22 | F(000) = 222 |
Triclinic, P1 | Dx = 1.469 Mg m−3 |
a = 6.9638 (12) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.2581 (14) Å | Cell parameters from 1772 reflections |
c = 9.7321 (17) Å | θ = 2.3–26.0° |
α = 107.012 (2)° | µ = 4.12 mm−1 |
β = 106.981 (2)° | T = 295 K |
γ = 99.193 (2)° | Block, colourless |
V = 493.11 (15) Å3 | 0.28 × 0.27 × 0.07 mm |
Bruker SMART CCD diffractometer | 1818 independent reflections |
Radiation source: fine-focus sealed tube | 1567 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
phi and ω scans | θmax = 25.5°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→8 |
Tmin = 0.391, Tmax = 0.764 | k = −9→9 |
3675 measured reflections | l = −11→11 |
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)] = 0.025 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.063 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0346P)2 + 0.0096P] where P = (Fo2 + 2Fc2)/3 |
1818 reflections | (Δ/σ)max = 0.001 |
101 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C18H28Br2O2 | γ = 99.193 (2)° |
Mr = 436.22 | V = 493.11 (15) Å3 |
Triclinic, P1 | Z = 1 |
a = 6.9638 (12) Å | Mo Kα radiation |
b = 8.2581 (14) Å | µ = 4.12 mm−1 |
c = 9.7321 (17) Å | T = 295 K |
α = 107.012 (2)° | 0.28 × 0.27 × 0.07 mm |
β = 106.981 (2)° |
Bruker SMART CCD diffractometer | 1818 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1567 reflections with I > 2σ(I) |
Tmin = 0.391, Tmax = 0.764 | Rint = 0.018 |
3675 measured reflections |
R[F2 > 2σ(F2)] = 0.025 | 0 restraints |
wR(F2) = 0.063 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.31 e Å−3 |
1818 reflections | Δρmin = −0.23 e Å−3 |
101 parameters |
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 | 0.07253 (4) | 0.51292 (4) | −0.31314 (3) | 0.05768 (13) | |
O1 | 0.3731 (2) | 0.6878 (2) | 0.00755 (19) | 0.0577 (5) | |
C1 | −0.1596 (3) | 0.4127 (3) | −0.1410 (3) | 0.0455 (6) | |
H1 | −0.2656 | 0.3549 | −0.2366 | 0.055* | |
C2 | 0.0292 (3) | 0.5069 (3) | −0.1316 (3) | 0.0418 (5) | |
C3 | 0.1932 (3) | 0.5970 (3) | 0.0107 (3) | 0.0426 (5) | |
C4 | 0.5450 (3) | 0.7726 (4) | 0.1511 (3) | 0.0513 (6) | |
H4A | 0.5871 | 0.6864 | 0.1944 | 0.062* | |
H4B | 0.5056 | 0.8560 | 0.2240 | 0.062* | |
C5 | 0.7229 (3) | 0.8672 (3) | 0.1183 (3) | 0.0528 (6) | |
H5A | 0.6775 | 0.9504 | 0.0722 | 0.063* | |
H5B | 0.7610 | 0.7824 | 0.0455 | 0.063* | |
C6 | 0.9133 (3) | 0.9647 (3) | 0.2665 (3) | 0.0539 (6) | |
H6A | 0.8755 | 1.0516 | 0.3377 | 0.065* | |
H6B | 0.9547 | 0.8817 | 0.3143 | 0.065* | |
C7 | 1.0979 (3) | 1.0563 (3) | 0.2370 (3) | 0.0518 (6) | |
H7A | 1.1351 | 0.9693 | 0.1653 | 0.062* | |
H7B | 1.0564 | 1.1394 | 0.1894 | 0.062* | |
C8 | 1.2870 (4) | 1.1524 (4) | 0.3828 (3) | 0.0662 (8) | |
H8A | 1.3355 | 1.0679 | 0.4259 | 0.079* | |
H8B | 1.2471 | 1.2326 | 0.4576 | 0.079* | |
C9 | 1.4646 (4) | 1.2556 (5) | 0.3548 (4) | 0.0850 (10) | |
H9A | 1.5032 | 1.1771 | 0.2795 | 0.127* | |
H9B | 1.5824 | 1.3105 | 0.4494 | 0.127* | |
H9C | 1.4200 | 1.3442 | 0.3179 | 0.127* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.05214 (17) | 0.0815 (2) | 0.03895 (16) | 0.00640 (13) | 0.01726 (12) | 0.02627 (13) |
O1 | 0.0382 (9) | 0.0797 (12) | 0.0427 (9) | −0.0082 (8) | 0.0094 (7) | 0.0224 (9) |
C1 | 0.0369 (12) | 0.0546 (14) | 0.0350 (12) | 0.0026 (10) | 0.0057 (9) | 0.0142 (11) |
C2 | 0.0414 (12) | 0.0529 (14) | 0.0330 (11) | 0.0089 (10) | 0.0135 (10) | 0.0199 (10) |
C3 | 0.0354 (11) | 0.0501 (13) | 0.0392 (12) | 0.0049 (10) | 0.0115 (10) | 0.0168 (11) |
C4 | 0.0368 (12) | 0.0633 (16) | 0.0417 (13) | −0.0004 (11) | 0.0082 (10) | 0.0151 (12) |
C5 | 0.0383 (12) | 0.0654 (16) | 0.0481 (14) | 0.0015 (11) | 0.0139 (11) | 0.0193 (12) |
C6 | 0.0399 (13) | 0.0629 (17) | 0.0504 (14) | 0.0023 (12) | 0.0136 (11) | 0.0172 (13) |
C7 | 0.0404 (13) | 0.0562 (15) | 0.0535 (15) | 0.0043 (11) | 0.0175 (11) | 0.0160 (12) |
C8 | 0.0437 (14) | 0.0786 (19) | 0.0592 (17) | −0.0001 (13) | 0.0128 (13) | 0.0150 (15) |
C9 | 0.0468 (16) | 0.095 (2) | 0.086 (2) | −0.0123 (15) | 0.0179 (16) | 0.0156 (19) |
Br1—C2 | 1.891 (2) | C5—H5B | 0.9700 |
O1—C3 | 1.367 (2) | C6—C7 | 1.529 (3) |
O1—C4 | 1.435 (3) | C6—H6A | 0.9700 |
C1—C3i | 1.377 (3) | C6—H6B | 0.9700 |
C1—C2 | 1.379 (3) | C7—C8 | 1.514 (3) |
C1—H1 | 0.9300 | C7—H7A | 0.9700 |
C2—C3 | 1.406 (3) | C7—H7B | 0.9700 |
C3—C1i | 1.377 (3) | C8—C9 | 1.525 (4) |
C4—C5 | 1.522 (3) | C8—H8A | 0.9700 |
C4—H4A | 0.9700 | C8—H8B | 0.9700 |
C4—H4B | 0.9700 | C9—H9A | 0.9600 |
C5—C6 | 1.533 (3) | C9—H9B | 0.9600 |
C5—H5A | 0.9700 | C9—H9C | 0.9600 |
C3—O1—C4 | 117.26 (18) | C7—C6—H6A | 109.1 |
C3i—C1—C2 | 120.9 (2) | C5—C6—H6A | 109.1 |
C3i—C1—H1 | 119.6 | C7—C6—H6B | 109.1 |
C2—C1—H1 | 119.6 | C5—C6—H6B | 109.1 |
C1—C2—C3 | 121.5 (2) | H6A—C6—H6B | 107.9 |
C1—C2—Br1 | 119.81 (16) | C8—C7—C6 | 112.7 (2) |
C3—C2—Br1 | 118.73 (16) | C8—C7—H7A | 109.1 |
O1—C3—C1i | 125.49 (19) | C6—C7—H7A | 109.1 |
O1—C3—C2 | 116.8 (2) | C8—C7—H7B | 109.1 |
C1i—C3—C2 | 117.70 (19) | C6—C7—H7B | 109.1 |
O1—C4—C5 | 107.30 (19) | H7A—C7—H7B | 107.8 |
O1—C4—H4A | 110.3 | C7—C8—C9 | 112.5 (3) |
C5—C4—H4A | 110.3 | C7—C8—H8A | 109.1 |
O1—C4—H4B | 110.3 | C9—C8—H8A | 109.1 |
C5—C4—H4B | 110.3 | C7—C8—H8B | 109.1 |
H4A—C4—H4B | 108.5 | C9—C8—H8B | 109.1 |
C4—C5—C6 | 111.0 (2) | H8A—C8—H8B | 107.8 |
C4—C5—H5A | 109.4 | C8—C9—H9A | 109.5 |
C6—C5—H5A | 109.4 | C8—C9—H9B | 109.5 |
C4—C5—H5B | 109.4 | H9A—C9—H9B | 109.5 |
C6—C5—H5B | 109.4 | C8—C9—H9C | 109.5 |
H5A—C5—H5B | 108.0 | H9A—C9—H9C | 109.5 |
C7—C6—C5 | 112.4 (2) | H9B—C9—H9C | 109.5 |
C3i—C1—C2—C3 | −0.4 (4) | Br1—C2—C3—C1i | −178.52 (18) |
C3i—C1—C2—Br1 | 178.49 (18) | C3—O1—C4—C5 | −178.7 (2) |
C4—O1—C3—C1i | 3.4 (4) | O1—C4—C5—C6 | 179.1 (2) |
C4—O1—C3—C2 | −176.9 (2) | C4—C5—C6—C7 | 178.1 (2) |
C1—C2—C3—O1 | −179.4 (2) | C5—C6—C7—C8 | −179.8 (2) |
Br1—C2—C3—O1 | 1.7 (3) | C6—C7—C8—C9 | −175.4 (2) |
C1—C2—C3—C1i | 0.4 (4) |
Symmetry code: (i) −x, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C18H28Br2O2 |
Mr | 436.22 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 295 |
a, b, c (Å) | 6.9638 (12), 8.2581 (14), 9.7321 (17) |
α, β, γ (°) | 107.012 (2), 106.981 (2), 99.193 (2) |
V (Å3) | 493.11 (15) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 4.12 |
Crystal size (mm) | 0.28 × 0.27 × 0.07 |
Data collection | |
Diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.391, 0.764 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3675, 1818, 1567 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.025, 0.063, 1.06 |
No. of reflections | 1818 |
No. of parameters | 101 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.23 |
Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Noncovalent interactions play an important role in designing superstructures (Brammer, 2004). Among these weak forces, the intermolecular interactions between halogen atoms have been a subject of interest (Desiraju et al., 1989). In order to gain more insight into the structure-regulating ability of intermolecular Br···Br interactions, herein we report the crystal structure of the title compound.
A view of the centrosymmetric molecular structure of the title compound is given in Fig.1. The alkyl chains are in the fully extended all-trans conformation and each of them is almost perfectly planar. The C—C—O—C torsion angles of 3.4 (4)o, indicate that the two alkyl chains are coplanar with the benzene ring. The crystal structure of the titile compound reveals the presence of a near linear C—Br···Br fragment[C—Br···Br=155.6 (3)o], the Br···Br distance (3.410 Å) is shorter than the sum of van der Waals radii(3.72 Å) and those in the other compound [3.634 (4)–3.9527 (9) Å](Kuriger et al., 2008; Ali et al., 2008). Owing to the intermolecular Br···Br interactions, the crystal structure of the title compound is extended to a one-dimensional chain structure. The chains are intercalated by van der Waals forces (Fig.2).