In the title compound, C
13H
14ClN, the cyclohexane ring adopts a chair conformation with an axial nitrile substituent. Intermolecular Ar—H
N bridges stabilize the crystal packing.
Supporting information
CCDC reference: 636132
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (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
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
C13H14ClN | F(000) = 464 |
Mr = 219.7 | Dx = 1.279 Mg m−3 |
Monoclinic, P21/c | Melting point = 370.5–371.5 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 7.7680 (5) Å | Cell parameters from 886 reflections |
b = 11.9121 (9) Å | θ = 2.8–28.2° |
c = 12.9065 (8) Å | µ = 0.3 mm−1 |
β = 107.129 (4)° | T = 173 K |
V = 1141.31 (13) Å3 | Plate, colourless |
Z = 4 | 0.50 × 0.50 × 0.08 mm |
Data collection top
Bruker SMART 1K CCD area-detector diffractometer | 2247 reflections with I > 2σ(I) |
ω scans | Rint = 0.071 |
Absorption correction: gaussian (SAINT-Plus; Bruker, 1999) | θmax = 28.0°, θmin = 2.4° |
Tmin = 0.864, Tmax = 0.976 | h = −10→10 |
9233 measured reflections | k = −15→13 |
2762 independent reflections | l = −17→17 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.035 | w = 1/[σ2(Fo2) + (0.0453P)2 + 0.1882P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.098 | (Δ/σ)max = 0.001 |
S = 1.05 | Δρmax = 0.26 e Å−3 |
2762 reflections | Δρmin = −0.26 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 | 0.49896 (16) | 0.28910 (10) | 0.86744 (9) | 0.0231 (2) | |
C2 | 0.63947 (17) | 0.32099 (11) | 0.97667 (10) | 0.0296 (3) | |
H2A | 0.5763 | 0.3541 | 1.0257 | 0.036* | |
H2B | 0.7019 | 0.2522 | 1.0116 | 0.036* | |
C3 | 0.77914 (19) | 0.40489 (12) | 0.96081 (11) | 0.0364 (3) | |
H3A | 0.7181 | 0.4759 | 0.931 | 0.044* | |
H3B | 0.8674 | 0.4217 | 1.0318 | 0.044* | |
C4 | 0.87786 (19) | 0.35836 (14) | 0.88387 (12) | 0.0397 (3) | |
H4A | 0.9479 | 0.2911 | 0.9166 | 0.048* | |
H4B | 0.9632 | 0.4154 | 0.8725 | 0.048* | |
C5 | 0.74413 (18) | 0.32705 (13) | 0.77487 (11) | 0.0349 (3) | |
H5A | 0.683 | 0.3957 | 0.7388 | 0.042* | |
H5B | 0.8099 | 0.2932 | 0.7276 | 0.042* | |
C6 | 0.60351 (17) | 0.24399 (10) | 0.79002 (10) | 0.0274 (3) | |
H6A | 0.6642 | 0.1729 | 0.8197 | 0.033* | |
H6B | 0.5166 | 0.2274 | 0.7185 | 0.033* | |
C7 | 0.40222 (17) | 0.39522 (11) | 0.82477 (10) | 0.0286 (3) | |
C8 | 0.35976 (16) | 0.20180 (10) | 0.87920 (10) | 0.0250 (3) | |
C9 | 0.20707 (17) | 0.17233 (11) | 0.79371 (10) | 0.0288 (3) | |
C10 | 0.08526 (19) | 0.09123 (12) | 0.80465 (12) | 0.0370 (3) | |
H10 | −0.0177 | 0.0744 | 0.7456 | 0.044* | |
C11 | 0.1151 (2) | 0.03503 (13) | 0.90249 (13) | 0.0417 (4) | |
H11 | 0.0336 | −0.0215 | 0.9103 | 0.05* | |
C12 | 0.2632 (2) | 0.06141 (12) | 0.98832 (12) | 0.0393 (3) | |
H12 | 0.2837 | 0.0231 | 1.0554 | 0.047* | |
C13 | 0.38301 (18) | 0.14423 (11) | 0.97690 (10) | 0.0318 (3) | |
H13 | 0.4834 | 0.1622 | 1.0372 | 0.038* | |
N1 | 0.33352 (17) | 0.47953 (11) | 0.79717 (11) | 0.0443 (3) | |
Cl1 | 0.15964 (5) | 0.23644 (3) | 0.66615 (3) | 0.04022 (13) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0251 (6) | 0.0214 (6) | 0.0212 (5) | 0.0002 (4) | 0.0042 (4) | −0.0010 (4) |
C2 | 0.0321 (6) | 0.0302 (6) | 0.0224 (6) | −0.0008 (5) | 0.0017 (5) | −0.0030 (5) |
C3 | 0.0356 (7) | 0.0326 (7) | 0.0328 (7) | −0.0086 (6) | −0.0025 (6) | −0.0041 (6) |
C4 | 0.0282 (7) | 0.0465 (9) | 0.0399 (8) | −0.0107 (6) | 0.0033 (6) | 0.0003 (7) |
C5 | 0.0298 (7) | 0.0433 (8) | 0.0317 (7) | −0.0078 (6) | 0.0092 (5) | 0.0000 (6) |
C6 | 0.0274 (6) | 0.0293 (6) | 0.0258 (6) | −0.0022 (5) | 0.0084 (5) | −0.0034 (5) |
C7 | 0.0274 (6) | 0.0264 (6) | 0.0294 (6) | −0.0018 (5) | 0.0042 (5) | −0.0003 (5) |
C8 | 0.0279 (6) | 0.0229 (6) | 0.0257 (6) | 0.0005 (5) | 0.0104 (5) | −0.0024 (5) |
C9 | 0.0309 (6) | 0.0297 (6) | 0.0269 (6) | −0.0032 (5) | 0.0101 (5) | −0.0031 (5) |
C10 | 0.0354 (7) | 0.0379 (8) | 0.0418 (7) | −0.0111 (6) | 0.0177 (6) | −0.0123 (6) |
C11 | 0.0490 (9) | 0.0326 (7) | 0.0542 (9) | −0.0117 (6) | 0.0320 (7) | −0.0067 (6) |
C12 | 0.0524 (9) | 0.0325 (7) | 0.0406 (7) | 0.0007 (6) | 0.0255 (7) | 0.0063 (6) |
C13 | 0.0366 (7) | 0.0314 (7) | 0.0289 (6) | 0.0018 (6) | 0.0122 (5) | 0.0020 (5) |
N1 | 0.0415 (7) | 0.0317 (7) | 0.0540 (8) | 0.0047 (5) | 0.0055 (6) | 0.0069 (6) |
Cl1 | 0.0343 (2) | 0.0536 (2) | 0.02695 (17) | −0.01255 (15) | −0.00002 (13) | 0.00102 (14) |
Geometric parameters (Å, º) top
C1—C7 | 1.4907 (17) | C5—H5B | 0.99 |
C1—C8 | 1.5395 (17) | C6—H6A | 0.99 |
C1—C2 | 1.5546 (16) | C6—H6B | 0.99 |
C1—C6 | 1.5571 (16) | C7—N1 | 1.1439 (18) |
C2—C3 | 1.5326 (19) | C8—C13 | 1.3995 (17) |
C2—H2A | 0.99 | C8—C9 | 1.4059 (18) |
C2—H2B | 0.99 | C9—C10 | 1.3882 (18) |
C3—C4 | 1.526 (2) | C9—Cl1 | 1.7527 (13) |
C3—H3A | 0.99 | C10—C11 | 1.387 (2) |
C3—H3B | 0.99 | C10—H10 | 0.95 |
C4—C5 | 1.5286 (19) | C11—C12 | 1.378 (2) |
C4—H4A | 0.99 | C11—H11 | 0.95 |
C4—H4B | 0.99 | C12—C13 | 1.3935 (19) |
C5—C6 | 1.5285 (17) | C12—H12 | 0.95 |
C5—H5A | 0.99 | C13—H13 | 0.95 |
| | | |
C7—C1—C8 | 108.48 (10) | C4—C5—H5B | 109.4 |
C7—C1—C2 | 105.70 (10) | H5A—C5—H5B | 108 |
C8—C1—C2 | 113.68 (10) | C5—C6—C1 | 112.72 (10) |
C7—C1—C6 | 110.92 (10) | C5—C6—H6A | 109 |
C8—C1—C6 | 110.14 (9) | C1—C6—H6A | 109 |
C2—C1—C6 | 107.85 (10) | C5—C6—H6B | 109 |
C3—C2—C1 | 111.96 (10) | C1—C6—H6B | 109 |
C3—C2—H2A | 109.2 | H6A—C6—H6B | 107.8 |
C1—C2—H2A | 109.2 | N1—C7—C1 | 176.21 (14) |
C3—C2—H2B | 109.2 | C13—C8—C9 | 116.10 (11) |
C1—C2—H2B | 109.2 | C13—C8—C1 | 120.78 (11) |
H2A—C2—H2B | 107.9 | C9—C8—C1 | 123.09 (11) |
C4—C3—C2 | 111.17 (11) | C10—C9—C8 | 122.46 (12) |
C4—C3—H3A | 109.4 | C10—C9—Cl1 | 115.96 (10) |
C2—C3—H3A | 109.4 | C8—C9—Cl1 | 121.58 (10) |
C4—C3—H3B | 109.4 | C11—C10—C9 | 119.50 (14) |
C2—C3—H3B | 109.4 | C11—C10—H10 | 120.3 |
H3A—C3—H3B | 108 | C9—C10—H10 | 120.3 |
C3—C4—C5 | 110.60 (11) | C12—C11—C10 | 119.85 (13) |
C3—C4—H4A | 109.5 | C12—C11—H11 | 120.1 |
C5—C4—H4A | 109.5 | C10—C11—H11 | 120.1 |
C3—C4—H4B | 109.5 | C11—C12—C13 | 120.12 (13) |
C5—C4—H4B | 109.5 | C11—C12—H12 | 119.9 |
H4A—C4—H4B | 108.1 | C13—C12—H12 | 119.9 |
C6—C5—C4 | 110.96 (11) | C12—C13—C8 | 121.96 (13) |
C6—C5—H5A | 109.4 | C12—C13—H13 | 119 |
C4—C5—H5A | 109.4 | C8—C13—H13 | 119 |
C6—C5—H5B | 109.4 | | |
| | | |
C7—C1—C2—C3 | −63.10 (13) | C2—C1—C8—C9 | 171.17 (11) |
C8—C1—C2—C3 | 178.03 (11) | C6—C1—C8—C9 | −67.67 (14) |
C6—C1—C2—C3 | 55.60 (13) | C13—C8—C9—C10 | 0.16 (18) |
C1—C2—C3—C4 | −57.82 (15) | C1—C8—C9—C10 | 178.20 (12) |
C2—C3—C4—C5 | 56.70 (16) | C13—C8—C9—Cl1 | −179.76 (10) |
C3—C4—C5—C6 | −55.99 (16) | C1—C8—C9—Cl1 | −1.72 (17) |
C4—C5—C6—C1 | 56.82 (15) | C8—C9—C10—C11 | −1.2 (2) |
C7—C1—C6—C5 | 59.86 (14) | Cl1—C9—C10—C11 | 178.77 (11) |
C8—C1—C6—C5 | 179.97 (10) | C9—C10—C11—C12 | 1.1 (2) |
C2—C1—C6—C5 | −55.45 (13) | C10—C11—C12—C13 | −0.1 (2) |
C7—C1—C8—C13 | −128.15 (12) | C11—C12—C13—C8 | −0.9 (2) |
C2—C1—C8—C13 | −10.89 (16) | C9—C8—C13—C12 | 0.89 (19) |
C6—C1—C8—C13 | 110.28 (13) | C1—C8—C13—C12 | −177.20 (11) |
C7—C1—C8—C9 | 53.90 (15) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···N1i | 0.95 | 2.61 | 3.4003 (19) | 141 |
Symmetry code: (i) −x, y−1/2, −z+3/2. |