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The cyclo­hexane ring in the title compound, C13H14BrN, adopts a chair conformation with an axial nitrile substituent. Ar—H...N bridges stabilize the crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807002929/bh2080sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807002929/bh2080Isup2.hkl
Contains datablock I

CCDC reference: 636134

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](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

Computing details top

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
C13H14BrNF(000) = 536
Mr = 264.16Dx = 1.506 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 871 reflections
a = 7.8650 (9) Åθ = 3.2–28.0°
b = 11.7892 (14) ŵ = 3.49 mm1
c = 13.1101 (13) ÅT = 173 K
β = 106.531 (5)°Plate, colourless
V = 1165.3 (2) Å30.6 × 0.3 × 0.1 mm
Z = 4
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
2220 reflections with I > 2σ(I)
ω scansRint = 0.043
Absorption correction: gaussian
(SAINT-Plus; Bruker, 1999)
θmax = 28.0°, θmin = 2.4°
Tmin = 0.243, Tmax = 0.715h = 810
7389 measured reflectionsk = 1015
2821 independent reflectionsl = 1717
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-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 = 0.98Δρmax = 0.45 e Å3
2821 reflectionsΔρmin = 0.65 e Å3
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
xyzUiso*/Ueq
C10.4947 (2)0.28881 (15)0.86889 (13)0.0241 (4)
C20.6304 (3)0.32354 (17)0.97527 (14)0.0310 (4)
H2A0.56610.35661.02310.037*
H2B0.69370.25511.01030.037*
C30.7657 (3)0.40976 (18)0.95888 (16)0.0386 (5)
H3A0.70390.48060.92880.046*
H3B0.85120.42811.02840.046*
C40.8650 (3)0.3629 (2)0.88410 (17)0.0433 (5)
H4A0.93610.29640.91750.052*
H4B0.94740.42130.87180.052*
C50.7372 (3)0.3278 (2)0.77784 (15)0.0376 (5)
H5A0.80480.29330.73260.045*
H5B0.67560.39580.74070.045*
C60.6000 (3)0.24274 (15)0.79407 (15)0.0287 (4)
H6A0.66130.17190.82450.034*
H6B0.5160.22420.72410.034*
C70.3972 (2)0.39492 (16)0.82563 (14)0.0291 (4)
C80.3589 (2)0.19922 (15)0.88222 (15)0.0257 (4)
C90.2093 (2)0.16706 (16)0.79929 (15)0.0297 (4)
C100.0920 (3)0.08460 (18)0.81301 (18)0.0412 (5)
H100.00910.06590.7560.049*
C110.1221 (3)0.02994 (19)0.90901 (19)0.0472 (6)
H110.04320.02770.91810.057*
C120.2677 (3)0.05926 (18)0.99254 (19)0.0446 (5)
H120.28910.02181.05910.054*
C130.3826 (3)0.14356 (17)0.97879 (15)0.0343 (4)
H130.48050.16391.03730.041*
N10.3296 (2)0.47976 (16)0.79813 (15)0.0439 (4)
Br10.15463 (3)0.23195 (2)0.660273 (16)0.04128 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0243 (8)0.0232 (9)0.0226 (8)0.0004 (7)0.0033 (7)0.0003 (7)
C20.0317 (10)0.0327 (11)0.0237 (9)0.0014 (8)0.0001 (7)0.0029 (8)
C30.0332 (10)0.0369 (11)0.0359 (11)0.0095 (9)0.0058 (8)0.0031 (9)
C40.0285 (10)0.0549 (14)0.0409 (11)0.0132 (10)0.0009 (9)0.0044 (10)
C50.0296 (10)0.0504 (14)0.0327 (10)0.0101 (9)0.0088 (8)0.0010 (9)
C60.0277 (9)0.0310 (10)0.0268 (9)0.0018 (7)0.0068 (7)0.0030 (7)
C70.0264 (9)0.0297 (11)0.0280 (9)0.0047 (8)0.0028 (7)0.0000 (8)
C80.0272 (9)0.0219 (9)0.0305 (9)0.0001 (7)0.0124 (7)0.0015 (7)
C90.0304 (9)0.0296 (10)0.0306 (9)0.0042 (8)0.0110 (8)0.0060 (8)
C100.0386 (11)0.0400 (12)0.0510 (12)0.0149 (9)0.0224 (10)0.0173 (10)
C110.0568 (14)0.0343 (12)0.0644 (15)0.0150 (11)0.0396 (12)0.0111 (11)
C120.0603 (14)0.0342 (12)0.0507 (13)0.0003 (10)0.0342 (12)0.0067 (10)
C130.0382 (10)0.0330 (11)0.0346 (10)0.0024 (9)0.0151 (9)0.0021 (8)
N10.0401 (10)0.0320 (10)0.0514 (11)0.0041 (8)0.0003 (8)0.0068 (8)
Br10.03315 (12)0.05399 (16)0.03009 (12)0.01046 (9)0.00169 (8)0.00392 (9)
Geometric parameters (Å, º) top
C1—C71.492 (3)C5—H5B0.99
C1—C81.547 (2)C6—H6A0.99
C1—C21.551 (2)C6—H6B0.99
C1—C61.551 (2)C7—N11.142 (3)
C2—C31.530 (3)C8—C131.391 (3)
C2—H2A0.99C8—C91.407 (3)
C2—H2B0.99C9—C101.387 (3)
C3—C41.520 (3)C9—Br11.9094 (19)
C3—H3A0.99C10—C111.373 (3)
C3—H3B0.99C10—H100.95
C4—C51.524 (3)C11—C121.385 (3)
C4—H4A0.99C11—H110.95
C4—H4B0.99C12—C131.389 (3)
C5—C61.532 (3)C12—H120.95
C5—H5A0.99C13—H130.95
C7—C1—C8108.58 (15)C6—C5—H5B109.4
C7—C1—C2105.56 (15)H5A—C5—H5B108
C8—C1—C2113.53 (15)C5—C6—C1112.50 (15)
C7—C1—C6111.24 (15)C5—C6—H6A109.1
C8—C1—C6110.03 (14)C1—C6—H6A109.1
C2—C1—C6107.84 (15)C5—C6—H6B109.1
C3—C2—C1112.17 (15)C1—C6—H6B109.1
C3—C2—H2A109.2H6A—C6—H6B107.8
C1—C2—H2A109.2N1—C7—C1175.5 (2)
C3—C2—H2B109.2C13—C8—C9116.25 (17)
C1—C2—H2B109.2C13—C8—C1120.46 (17)
H2A—C2—H2B107.9C9—C8—C1123.27 (16)
C4—C3—C2110.75 (17)C10—C9—C8121.94 (19)
C4—C3—H3A109.5C10—C9—Br1115.29 (15)
C2—C3—H3A109.5C8—C9—Br1122.77 (13)
C4—C3—H3B109.5C11—C10—C9120.0 (2)
C2—C3—H3B109.5C11—C10—H10120
H3A—C3—H3B108.1C9—C10—H10120
C3—C4—C5111.23 (16)C10—C11—C12119.70 (19)
C3—C4—H4A109.4C10—C11—H11120.2
C5—C4—H4A109.4C12—C11—H11120.2
C3—C4—H4B109.4C11—C12—C13119.9 (2)
C5—C4—H4B109.4C11—C12—H12120.1
H4A—C4—H4B108C13—C12—H12120.1
C4—C5—C6110.95 (16)C12—C13—C8122.2 (2)
C4—C5—H5A109.4C12—C13—H13118.9
C6—C5—H5A109.4C8—C13—H13118.9
C4—C5—H5B109.4
C7—C1—C2—C362.7 (2)C2—C1—C8—C9170.83 (16)
C8—C1—C2—C3178.45 (15)C6—C1—C8—C968.2 (2)
C6—C1—C2—C356.3 (2)C13—C8—C9—C100.1 (3)
C1—C2—C3—C457.8 (2)C1—C8—C9—C10178.52 (17)
C2—C3—C4—C556.3 (2)C13—C8—C9—Br1179.26 (14)
C3—C4—C5—C655.6 (2)C1—C8—C9—Br10.8 (2)
C4—C5—C6—C156.4 (2)C8—C9—C10—C111.4 (3)
C7—C1—C6—C559.7 (2)Br1—C9—C10—C11177.98 (16)
C8—C1—C6—C5179.91 (15)C9—C10—C11—C121.4 (3)
C2—C1—C6—C555.6 (2)C10—C11—C12—C130.1 (3)
C7—C1—C8—C13127.85 (18)C11—C12—C13—C81.3 (3)
C2—C1—C8—C1310.8 (2)C9—C8—C13—C121.3 (3)
C6—C1—C8—C13110.18 (19)C1—C8—C13—C12177.21 (17)
C7—C1—C8—C953.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···N1i0.952.623.449 (3)146
Symmetry code: (i) x, y1/2, z+3/2.
 

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