Download citation
Download citation
link to html
In the title compound, C13H14ClN, the cyclo­hexane ring adopts a chair conformation with an axial nitrile substituent. Inter­molecular Ar—H...N bridges stabilize the crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807002917/bh2074sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807002917/bh2074Isup2.hkl
Contains datablock I

CCDC reference: 636132

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.035
  • wR factor = 0.098
  • Data-to-parameter ratio = 20.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C7 .. 6.95 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-Chlorophenyl)cyclohexanecarbonitrile top
Crystal data top
C13H14ClNF(000) = 464
Mr = 219.7Dx = 1.279 Mg m3
Monoclinic, P21/cMelting point = 370.5–371.5 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 7.7680 (5) ÅCell parameters from 886 reflections
b = 11.9121 (9) Åθ = 2.8–28.2°
c = 12.9065 (8) ŵ = 0.3 mm1
β = 107.129 (4)°T = 173 K
V = 1141.31 (13) Å3Plate, colourless
Z = 40.50 × 0.50 × 0.08 mm
Data collection top
Bruker SMART 1K CCD area-detector
diffractometer
2247 reflections with I > 2σ(I)
ω scansRint = 0.071
Absorption correction: gaussian
(SAINT-Plus; Bruker, 1999)
θmax = 28.0°, θmin = 2.4°
Tmin = 0.864, Tmax = 0.976h = 1010
9233 measured reflectionsk = 1513
2762 independent reflectionsl = 1717
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.035 w = 1/[σ2(Fo2) + (0.0453P)2 + 0.1882P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.098(Δ/σ)max = 0.001
S = 1.05Δρmax = 0.26 e Å3
2762 reflectionsΔρmin = 0.26 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
C10.49896 (16)0.28910 (10)0.86744 (9)0.0231 (2)
C20.63947 (17)0.32099 (11)0.97667 (10)0.0296 (3)
H2A0.57630.35411.02570.036*
H2B0.70190.25221.01160.036*
C30.77914 (19)0.40489 (12)0.96081 (11)0.0364 (3)
H3A0.71810.47590.9310.044*
H3B0.86740.42171.03180.044*
C40.87786 (19)0.35836 (14)0.88387 (12)0.0397 (3)
H4A0.94790.29110.91660.048*
H4B0.96320.41540.87250.048*
C50.74413 (18)0.32705 (13)0.77487 (11)0.0349 (3)
H5A0.6830.39570.73880.042*
H5B0.80990.29320.72760.042*
C60.60351 (17)0.24399 (10)0.79002 (10)0.0274 (3)
H6A0.66420.17290.81970.033*
H6B0.51660.22740.71850.033*
C70.40222 (17)0.39522 (11)0.82477 (10)0.0286 (3)
C80.35976 (16)0.20180 (10)0.87920 (10)0.0250 (3)
C90.20707 (17)0.17233 (11)0.79371 (10)0.0288 (3)
C100.08526 (19)0.09123 (12)0.80465 (12)0.0370 (3)
H100.01770.07440.74560.044*
C110.1151 (2)0.03503 (13)0.90249 (13)0.0417 (4)
H110.03360.02150.91030.05*
C120.2632 (2)0.06141 (12)0.98832 (12)0.0393 (3)
H120.28370.02311.05540.047*
C130.38301 (18)0.14423 (11)0.97690 (10)0.0318 (3)
H130.48340.16221.03720.038*
N10.33352 (17)0.47953 (11)0.79717 (11)0.0443 (3)
Cl10.15964 (5)0.23644 (3)0.66615 (3)0.04022 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0251 (6)0.0214 (6)0.0212 (5)0.0002 (4)0.0042 (4)0.0010 (4)
C20.0321 (6)0.0302 (6)0.0224 (6)0.0008 (5)0.0017 (5)0.0030 (5)
C30.0356 (7)0.0326 (7)0.0328 (7)0.0086 (6)0.0025 (6)0.0041 (6)
C40.0282 (7)0.0465 (9)0.0399 (8)0.0107 (6)0.0033 (6)0.0003 (7)
C50.0298 (7)0.0433 (8)0.0317 (7)0.0078 (6)0.0092 (5)0.0000 (6)
C60.0274 (6)0.0293 (6)0.0258 (6)0.0022 (5)0.0084 (5)0.0034 (5)
C70.0274 (6)0.0264 (6)0.0294 (6)0.0018 (5)0.0042 (5)0.0003 (5)
C80.0279 (6)0.0229 (6)0.0257 (6)0.0005 (5)0.0104 (5)0.0024 (5)
C90.0309 (6)0.0297 (6)0.0269 (6)0.0032 (5)0.0101 (5)0.0031 (5)
C100.0354 (7)0.0379 (8)0.0418 (7)0.0111 (6)0.0177 (6)0.0123 (6)
C110.0490 (9)0.0326 (7)0.0542 (9)0.0117 (6)0.0320 (7)0.0067 (6)
C120.0524 (9)0.0325 (7)0.0406 (7)0.0007 (6)0.0255 (7)0.0063 (6)
C130.0366 (7)0.0314 (7)0.0289 (6)0.0018 (6)0.0122 (5)0.0020 (5)
N10.0415 (7)0.0317 (7)0.0540 (8)0.0047 (5)0.0055 (6)0.0069 (6)
Cl10.0343 (2)0.0536 (2)0.02695 (17)0.01255 (15)0.00002 (13)0.00102 (14)
Geometric parameters (Å, º) top
C1—C71.4907 (17)C5—H5B0.99
C1—C81.5395 (17)C6—H6A0.99
C1—C21.5546 (16)C6—H6B0.99
C1—C61.5571 (16)C7—N11.1439 (18)
C2—C31.5326 (19)C8—C131.3995 (17)
C2—H2A0.99C8—C91.4059 (18)
C2—H2B0.99C9—C101.3882 (18)
C3—C41.526 (2)C9—Cl11.7527 (13)
C3—H3A0.99C10—C111.387 (2)
C3—H3B0.99C10—H100.95
C4—C51.5286 (19)C11—C121.378 (2)
C4—H4A0.99C11—H110.95
C4—H4B0.99C12—C131.3935 (19)
C5—C61.5285 (17)C12—H120.95
C5—H5A0.99C13—H130.95
C7—C1—C8108.48 (10)C4—C5—H5B109.4
C7—C1—C2105.70 (10)H5A—C5—H5B108
C8—C1—C2113.68 (10)C5—C6—C1112.72 (10)
C7—C1—C6110.92 (10)C5—C6—H6A109
C8—C1—C6110.14 (9)C1—C6—H6A109
C2—C1—C6107.85 (10)C5—C6—H6B109
C3—C2—C1111.96 (10)C1—C6—H6B109
C3—C2—H2A109.2H6A—C6—H6B107.8
C1—C2—H2A109.2N1—C7—C1176.21 (14)
C3—C2—H2B109.2C13—C8—C9116.10 (11)
C1—C2—H2B109.2C13—C8—C1120.78 (11)
H2A—C2—H2B107.9C9—C8—C1123.09 (11)
C4—C3—C2111.17 (11)C10—C9—C8122.46 (12)
C4—C3—H3A109.4C10—C9—Cl1115.96 (10)
C2—C3—H3A109.4C8—C9—Cl1121.58 (10)
C4—C3—H3B109.4C11—C10—C9119.50 (14)
C2—C3—H3B109.4C11—C10—H10120.3
H3A—C3—H3B108C9—C10—H10120.3
C3—C4—C5110.60 (11)C12—C11—C10119.85 (13)
C3—C4—H4A109.5C12—C11—H11120.1
C5—C4—H4A109.5C10—C11—H11120.1
C3—C4—H4B109.5C11—C12—C13120.12 (13)
C5—C4—H4B109.5C11—C12—H12119.9
H4A—C4—H4B108.1C13—C12—H12119.9
C6—C5—C4110.96 (11)C12—C13—C8121.96 (13)
C6—C5—H5A109.4C12—C13—H13119
C4—C5—H5A109.4C8—C13—H13119
C6—C5—H5B109.4
C7—C1—C2—C363.10 (13)C2—C1—C8—C9171.17 (11)
C8—C1—C2—C3178.03 (11)C6—C1—C8—C967.67 (14)
C6—C1—C2—C355.60 (13)C13—C8—C9—C100.16 (18)
C1—C2—C3—C457.82 (15)C1—C8—C9—C10178.20 (12)
C2—C3—C4—C556.70 (16)C13—C8—C9—Cl1179.76 (10)
C3—C4—C5—C655.99 (16)C1—C8—C9—Cl11.72 (17)
C4—C5—C6—C156.82 (15)C8—C9—C10—C111.2 (2)
C7—C1—C6—C559.86 (14)Cl1—C9—C10—C11178.77 (11)
C8—C1—C6—C5179.97 (10)C9—C10—C11—C121.1 (2)
C2—C1—C6—C555.45 (13)C10—C11—C12—C130.1 (2)
C7—C1—C8—C13128.15 (12)C11—C12—C13—C80.9 (2)
C2—C1—C8—C1310.89 (16)C9—C8—C13—C120.89 (19)
C6—C1—C8—C13110.28 (13)C1—C8—C13—C12177.20 (11)
C7—C1—C8—C953.90 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···N1i0.952.613.4003 (19)141
Symmetry code: (i) x, y1/2, z+3/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds