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The cyclohexane ring in the title compound, C
13H
14BrN, adopts a chair conformation with an axial nitrile substituent. Ar—H
N bridges stabilize the crystal packing.
Supporting information
CCDC reference: 636134
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
- R factor = 0.029
- wR factor = 0.072
- Data-to-parameter ratio = 20.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C7 .. 6.41 su
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
1 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
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART-NT (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg,
1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).
1-(2-Bromophenyl)cyclohexanecarbonitrile
top
Crystal data top
C13H14BrN | F(000) = 536 |
Mr = 264.16 | Dx = 1.506 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 871 reflections |
a = 7.8650 (9) Å | θ = 3.2–28.0° |
b = 11.7892 (14) Å | µ = 3.49 mm−1 |
c = 13.1101 (13) Å | T = 173 K |
β = 106.531 (5)° | Plate, colourless |
V = 1165.3 (2) Å3 | 0.6 × 0.3 × 0.1 mm |
Z = 4 | |
Data collection top
Bruker SMART 1K CCD area-detector diffractometer | 2220 reflections with I > 2σ(I) |
ω scans | Rint = 0.043 |
Absorption correction: gaussian (SAINT-Plus; Bruker, 1999) | θmax = 28.0°, θmin = 2.4° |
Tmin = 0.243, Tmax = 0.715 | h = −8→10 |
7389 measured reflections | k = −10→15 |
2821 independent reflections | l = −17→17 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.029 | w = 1/[σ2(Fo2) + (0.0406P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.072 | (Δ/σ)max = 0.006 |
S = 0.98 | Δρmax = 0.45 e Å−3 |
2821 reflections | Δρmin = −0.65 e Å−3 |
136 parameters | |
Special details top
Experimental. Numerical integration absorption corrections based on indexed crystal faces were
applied using the XPREP routine (Bruker, 1999) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.4947 (2) | 0.28881 (15) | 0.86889 (13) | 0.0241 (4) | |
C2 | 0.6304 (3) | 0.32354 (17) | 0.97527 (14) | 0.0310 (4) | |
H2A | 0.5661 | 0.3566 | 1.0231 | 0.037* | |
H2B | 0.6937 | 0.2551 | 1.0103 | 0.037* | |
C3 | 0.7657 (3) | 0.40976 (18) | 0.95888 (16) | 0.0386 (5) | |
H3A | 0.7039 | 0.4806 | 0.9288 | 0.046* | |
H3B | 0.8512 | 0.4281 | 1.0284 | 0.046* | |
C4 | 0.8650 (3) | 0.3629 (2) | 0.88410 (17) | 0.0433 (5) | |
H4A | 0.9361 | 0.2964 | 0.9175 | 0.052* | |
H4B | 0.9474 | 0.4213 | 0.8718 | 0.052* | |
C5 | 0.7372 (3) | 0.3278 (2) | 0.77784 (15) | 0.0376 (5) | |
H5A | 0.8048 | 0.2933 | 0.7326 | 0.045* | |
H5B | 0.6756 | 0.3958 | 0.7407 | 0.045* | |
C6 | 0.6000 (3) | 0.24274 (15) | 0.79407 (15) | 0.0287 (4) | |
H6A | 0.6613 | 0.1719 | 0.8245 | 0.034* | |
H6B | 0.516 | 0.2242 | 0.7241 | 0.034* | |
C7 | 0.3972 (2) | 0.39492 (16) | 0.82563 (14) | 0.0291 (4) | |
C8 | 0.3589 (2) | 0.19922 (15) | 0.88222 (15) | 0.0257 (4) | |
C9 | 0.2093 (2) | 0.16706 (16) | 0.79929 (15) | 0.0297 (4) | |
C10 | 0.0920 (3) | 0.08460 (18) | 0.81301 (18) | 0.0412 (5) | |
H10 | −0.0091 | 0.0659 | 0.756 | 0.049* | |
C11 | 0.1221 (3) | 0.02994 (19) | 0.90901 (19) | 0.0472 (6) | |
H11 | 0.0432 | −0.0277 | 0.9181 | 0.057* | |
C12 | 0.2677 (3) | 0.05926 (18) | 0.99254 (19) | 0.0446 (5) | |
H12 | 0.2891 | 0.0218 | 1.0591 | 0.054* | |
C13 | 0.3826 (3) | 0.14356 (17) | 0.97879 (15) | 0.0343 (4) | |
H13 | 0.4805 | 0.1639 | 1.0373 | 0.041* | |
N1 | 0.3296 (2) | 0.47976 (16) | 0.79813 (15) | 0.0439 (4) | |
Br1 | 0.15463 (3) | 0.23195 (2) | 0.660273 (16) | 0.04128 (9) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0243 (8) | 0.0232 (9) | 0.0226 (8) | −0.0004 (7) | 0.0033 (7) | 0.0003 (7) |
C2 | 0.0317 (10) | 0.0327 (11) | 0.0237 (9) | −0.0014 (8) | 0.0001 (7) | −0.0029 (8) |
C3 | 0.0332 (10) | 0.0369 (11) | 0.0359 (11) | −0.0095 (9) | −0.0058 (8) | −0.0031 (9) |
C4 | 0.0285 (10) | 0.0549 (14) | 0.0409 (11) | −0.0132 (10) | 0.0009 (9) | 0.0044 (10) |
C5 | 0.0296 (10) | 0.0504 (14) | 0.0327 (10) | −0.0101 (9) | 0.0088 (8) | 0.0010 (9) |
C6 | 0.0277 (9) | 0.0310 (10) | 0.0268 (9) | −0.0018 (7) | 0.0068 (7) | −0.0030 (7) |
C7 | 0.0264 (9) | 0.0297 (11) | 0.0280 (9) | −0.0047 (8) | 0.0028 (7) | 0.0000 (8) |
C8 | 0.0272 (9) | 0.0219 (9) | 0.0305 (9) | 0.0001 (7) | 0.0124 (7) | −0.0015 (7) |
C9 | 0.0304 (9) | 0.0296 (10) | 0.0306 (9) | −0.0042 (8) | 0.0110 (8) | −0.0060 (8) |
C10 | 0.0386 (11) | 0.0400 (12) | 0.0510 (12) | −0.0149 (9) | 0.0224 (10) | −0.0173 (10) |
C11 | 0.0568 (14) | 0.0343 (12) | 0.0644 (15) | −0.0150 (11) | 0.0396 (12) | −0.0111 (11) |
C12 | 0.0603 (14) | 0.0342 (12) | 0.0507 (13) | −0.0003 (10) | 0.0342 (12) | 0.0067 (10) |
C13 | 0.0382 (10) | 0.0330 (11) | 0.0346 (10) | 0.0024 (9) | 0.0151 (9) | 0.0021 (8) |
N1 | 0.0401 (10) | 0.0320 (10) | 0.0514 (11) | 0.0041 (8) | −0.0003 (8) | 0.0068 (8) |
Br1 | 0.03315 (12) | 0.05399 (16) | 0.03009 (12) | −0.01046 (9) | −0.00169 (8) | −0.00392 (9) |
Geometric parameters (Å, º) top
C1—C7 | 1.492 (3) | C5—H5B | 0.99 |
C1—C8 | 1.547 (2) | C6—H6A | 0.99 |
C1—C2 | 1.551 (2) | C6—H6B | 0.99 |
C1—C6 | 1.551 (2) | C7—N1 | 1.142 (3) |
C2—C3 | 1.530 (3) | C8—C13 | 1.391 (3) |
C2—H2A | 0.99 | C8—C9 | 1.407 (3) |
C2—H2B | 0.99 | C9—C10 | 1.387 (3) |
C3—C4 | 1.520 (3) | C9—Br1 | 1.9094 (19) |
C3—H3A | 0.99 | C10—C11 | 1.373 (3) |
C3—H3B | 0.99 | C10—H10 | 0.95 |
C4—C5 | 1.524 (3) | C11—C12 | 1.385 (3) |
C4—H4A | 0.99 | C11—H11 | 0.95 |
C4—H4B | 0.99 | C12—C13 | 1.389 (3) |
C5—C6 | 1.532 (3) | C12—H12 | 0.95 |
C5—H5A | 0.99 | C13—H13 | 0.95 |
| | | |
C7—C1—C8 | 108.58 (15) | C6—C5—H5B | 109.4 |
C7—C1—C2 | 105.56 (15) | H5A—C5—H5B | 108 |
C8—C1—C2 | 113.53 (15) | C5—C6—C1 | 112.50 (15) |
C7—C1—C6 | 111.24 (15) | C5—C6—H6A | 109.1 |
C8—C1—C6 | 110.03 (14) | C1—C6—H6A | 109.1 |
C2—C1—C6 | 107.84 (15) | C5—C6—H6B | 109.1 |
C3—C2—C1 | 112.17 (15) | C1—C6—H6B | 109.1 |
C3—C2—H2A | 109.2 | H6A—C6—H6B | 107.8 |
C1—C2—H2A | 109.2 | N1—C7—C1 | 175.5 (2) |
C3—C2—H2B | 109.2 | C13—C8—C9 | 116.25 (17) |
C1—C2—H2B | 109.2 | C13—C8—C1 | 120.46 (17) |
H2A—C2—H2B | 107.9 | C9—C8—C1 | 123.27 (16) |
C4—C3—C2 | 110.75 (17) | C10—C9—C8 | 121.94 (19) |
C4—C3—H3A | 109.5 | C10—C9—Br1 | 115.29 (15) |
C2—C3—H3A | 109.5 | C8—C9—Br1 | 122.77 (13) |
C4—C3—H3B | 109.5 | C11—C10—C9 | 120.0 (2) |
C2—C3—H3B | 109.5 | C11—C10—H10 | 120 |
H3A—C3—H3B | 108.1 | C9—C10—H10 | 120 |
C3—C4—C5 | 111.23 (16) | C10—C11—C12 | 119.70 (19) |
C3—C4—H4A | 109.4 | C10—C11—H11 | 120.2 |
C5—C4—H4A | 109.4 | C12—C11—H11 | 120.2 |
C3—C4—H4B | 109.4 | C11—C12—C13 | 119.9 (2) |
C5—C4—H4B | 109.4 | C11—C12—H12 | 120.1 |
H4A—C4—H4B | 108 | C13—C12—H12 | 120.1 |
C4—C5—C6 | 110.95 (16) | C12—C13—C8 | 122.2 (2) |
C4—C5—H5A | 109.4 | C12—C13—H13 | 118.9 |
C6—C5—H5A | 109.4 | C8—C13—H13 | 118.9 |
C4—C5—H5B | 109.4 | | |
| | | |
C7—C1—C2—C3 | −62.7 (2) | C2—C1—C8—C9 | 170.83 (16) |
C8—C1—C2—C3 | 178.45 (15) | C6—C1—C8—C9 | −68.2 (2) |
C6—C1—C2—C3 | 56.3 (2) | C13—C8—C9—C10 | 0.1 (3) |
C1—C2—C3—C4 | −57.8 (2) | C1—C8—C9—C10 | 178.52 (17) |
C2—C3—C4—C5 | 56.3 (2) | C13—C8—C9—Br1 | −179.26 (14) |
C3—C4—C5—C6 | −55.6 (2) | C1—C8—C9—Br1 | −0.8 (2) |
C4—C5—C6—C1 | 56.4 (2) | C8—C9—C10—C11 | −1.4 (3) |
C7—C1—C6—C5 | 59.7 (2) | Br1—C9—C10—C11 | 177.98 (16) |
C8—C1—C6—C5 | −179.91 (15) | C9—C10—C11—C12 | 1.4 (3) |
C2—C1—C6—C5 | −55.6 (2) | C10—C11—C12—C13 | −0.1 (3) |
C7—C1—C8—C13 | −127.85 (18) | C11—C12—C13—C8 | −1.3 (3) |
C2—C1—C8—C13 | −10.8 (2) | C9—C8—C13—C12 | 1.3 (3) |
C6—C1—C8—C13 | 110.18 (19) | C1—C8—C13—C12 | −177.21 (17) |
C7—C1—C8—C9 | 53.8 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···N1i | 0.95 | 2.62 | 3.449 (3) | 146 |
Symmetry code: (i) −x, y−1/2, −z+3/2. |
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