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The molecule of the title compound, C
12H
10Br
2, displays crystallographic inversion symmetry and is essentially planar. Bond lengths show the typical naphthalene pattern. The crystal packing shows no short H
Br, Br
Br or C—H
π contacts.
Supporting information
CCDC reference: 271813
Key indicators
- Single-crystal X-ray study
- T = 133 K
- Mean (C-C) = 0.003 Å
- R factor = 0.024
- wR factor = 0.054
- Data-to-parameter ratio = 24.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.
1,5-Dibromo-2,6-dimethylnaphthalene
top
Crystal data top
C12H10Br2 | F(000) = 608 |
Mr = 314.02 | Dx = 1.986 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 20.543 (3) Å | Cell parameters from 4270 reflections |
b = 4.0082 (8) Å | θ = 2.7–30.7° |
c = 12.813 (2) Å | µ = 7.67 mm−1 |
β = 95.497 (6)° | T = 133 K |
V = 1050.2 (3) Å3 | Prism, colourless |
Z = 4 | 0.22 × 0.11 × 0.08 mm |
Data collection top
Bruker SMART 1000 CCD area-detector diffractometer | 1597 independent reflections |
Radiation source: fine-focus sealed tube | 1327 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 8.192 pixels mm-1 | θmax = 30.5°, θmin = 2.0° |
φ and ω scans | h = −28→28 |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | k = −5→5 |
Tmin = 0.383, Tmax = 0.541 | l = −18→18 |
8223 measured reflections | |
Refinement top
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)] = 0.024 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.054 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0241P)2 + 1.2229P] where P = (Fo2 + 2Fc2)/3 |
1597 reflections | (Δ/σ)max < 0.001 |
65 parameters | Δρmax = 0.48 e Å−3 |
0 restraints | Δρmin = −0.54 e Å−3 |
Special details top
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. Least-squares planes (x,y,z in crystal coordinates) and
deviations from them (* indicates atom used to define plane) - 2.3881 (0.0163) x - 3.5409 (0.0020) y + 5.9322 (0.0118)
z = 1.4788 (0.0092) * -0.0062 (0.0010) C1 * 0.0072 (0.0014) C2 * -0.0020 (0.0013) C3 * -0.0040
(0.0014) C4 * 0.0050 (0.0010) C5 Rms deviation of fitted atoms = 0.0052 - 2.3881 (0.0162) x + 3.5409 (0.0020) y + 5.9322 (0.0117)
z = 2.0537 (0.0051) Angle to previous plane (with approximate e.s.d.) = 55.88 (0.06) * -0.0062 (0.0010) C1_$1 * 0.0072 (0.0014) C2_$1 * -0.0020 (0.0013) C3_$1 *
-0.0040 (0.0014) C4_$1 * 0.0050 (0.0010) C5_$1 Rms deviation of fitted atoms = 0.0052 Operators for generating equivalent atoms: $1 x, -y + 1, z
- 1/2 |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Br | 0.403872 (9) | 0.02330 (5) | 0.419784 (15) | 0.02029 (7) | |
C1 | 0.34079 (9) | 0.2010 (5) | 0.50544 (15) | 0.0151 (4) | |
C2 | 0.36328 (10) | 0.3412 (5) | 0.60043 (15) | 0.0167 (4) | |
C3 | 0.31555 (10) | 0.4780 (5) | 0.66129 (15) | 0.0183 (4) | |
H3 | 0.3296 | 0.5794 | 0.7266 | 0.022* | |
C4 | 0.24995 (10) | 0.4691 (5) | 0.62925 (14) | 0.0170 (4) | |
H4 | 0.2197 | 0.5639 | 0.6724 | 0.020* | |
C5 | 0.22674 (9) | 0.3194 (5) | 0.53205 (14) | 0.0137 (4) | |
C6 | 0.43443 (10) | 0.3563 (6) | 0.64136 (17) | 0.0237 (4) | |
H6A | 0.4518 | 0.1293 | 0.6504 | 0.028* | |
H6B | 0.4389 | 0.4722 | 0.7090 | 0.028* | |
H6C | 0.4589 | 0.4773 | 0.5913 | 0.028* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br | 0.01682 (10) | 0.02422 (12) | 0.02071 (10) | 0.00378 (9) | 0.00631 (7) | 0.00021 (9) |
C1 | 0.0162 (9) | 0.0154 (9) | 0.0145 (8) | 0.0020 (7) | 0.0049 (7) | 0.0025 (7) |
C2 | 0.0173 (9) | 0.0180 (10) | 0.0147 (8) | −0.0016 (7) | 0.0008 (7) | 0.0033 (7) |
C3 | 0.0226 (10) | 0.0190 (10) | 0.0132 (8) | −0.0024 (8) | 0.0003 (7) | −0.0004 (8) |
C4 | 0.0200 (9) | 0.0177 (10) | 0.0138 (8) | −0.0013 (8) | 0.0047 (7) | −0.0001 (7) |
C5 | 0.0168 (9) | 0.0133 (9) | 0.0113 (8) | −0.0001 (7) | 0.0029 (7) | 0.0015 (7) |
C6 | 0.0191 (10) | 0.0279 (12) | 0.0233 (10) | −0.0003 (9) | −0.0021 (8) | −0.0005 (9) |
Geometric parameters (Å, º) top
Br—C1 | 1.9141 (19) | C5—C5i | 1.431 (4) |
C1—C2 | 1.379 (3) | C3—H3 | 0.9500 |
C1—C5i | 1.426 (3) | C4—H4 | 0.9500 |
C2—C3 | 1.420 (3) | C6—H6A | 0.9800 |
C2—C6 | 1.506 (3) | C6—H6B | 0.9800 |
C3—C4 | 1.371 (3) | C6—H6C | 0.9800 |
C4—C5 | 1.423 (3) | | |
| | | |
C2—C1—C5i | 123.59 (18) | C4—C3—H3 | 118.8 |
C2—C1—Br | 118.01 (15) | C2—C3—H3 | 118.8 |
C5i—C1—Br | 118.40 (14) | C3—C4—H4 | 119.7 |
C1—C2—C3 | 116.83 (18) | C5—C4—H4 | 119.7 |
C1—C2—C6 | 123.74 (19) | C2—C6—H6A | 109.5 |
C3—C2—C6 | 119.43 (18) | C2—C6—H6B | 109.5 |
C4—C3—C2 | 122.41 (18) | H6A—C6—H6B | 109.5 |
C3—C4—C5 | 120.69 (18) | C2—C6—H6C | 109.5 |
C4—C5—C1i | 123.54 (17) | H6A—C6—H6C | 109.5 |
C4—C5—C5i | 118.7 (2) | H6B—C6—H6C | 109.5 |
C1i—C5—C5i | 117.8 (2) | | |
| | | |
C5i—C1—C2—C3 | −1.6 (3) | C6—C2—C3—C4 | −179.2 (2) |
Br—C1—C2—C3 | 178.60 (14) | C2—C3—C4—C5 | 0.1 (3) |
C5i—C1—C2—C6 | 178.6 (2) | C3—C4—C5—C1i | 179.39 (19) |
Br—C1—C2—C6 | −1.2 (3) | C3—C4—C5—C5i | −0.5 (3) |
C1—C2—C3—C4 | 1.0 (3) | | |
Symmetry code: (i) −x+1/2, −y+1/2, −z+1. |
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