


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808036052/nc2117sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808036052/nc2117Isup2.hkl |
CCDC reference: 712400
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.043
- wR factor = 0.124
- Data-to-parameter ratio = 15.2
checkCIF/PLATON results
No syntax errors found
Alert level C Value of measurement temperature given = 273.000 Value of melting point given = 0.000 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.55 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 0 ALERT type 5 Informative message, check
A solution of 2,3-dichlorophenol (1.0 mmol), N-cyclohexyl-2-chloroacetamide (1.1 mmol), K2CO3 (1.1 mmol) and CH3CN (20 ml) was refluxed for 3 h. After completion of the reaction (by TLC monitoring), the solution was cooled and the solvent was evaporated under reduced pressure. The residue was poured into water and adjusted to pH 6–7 with dilute hydrochloric acid (10%) and extracted with ethyl acetate, washed with brine and dried over anhydrous MgSO4. And then the mixture was filtered and the filtrate obtained was concentrated under reduced pressure to obtain the corresponding crude product. The product was purified by column chromatography on silica gel using ethyl acetate as eluent (yield 90%). Crystals suitable for X-ray diffraction were obtained by slow evaparation of a solution of the solid dissolved in ethyl acetate/hexane at room temperature for 7 days.
All H atoms were placed in geometrically calculated positions with C—H = 0.97 Å for CH~2~ H atoms, C—H = 0.93 Å for CH H atoms and 0.86 Å for N-H H atoms and were refined isotropic with Uiso(H) = 1.2 Ueq of the parent atom using a riding model.
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![]() | Fig. 1. The molecular structure of the title compound with labelling and displacement ellipsoids drawn at 50% probability level. |
C14H17Cl2NO2 | F(000) = 632 |
Mr = 302.19 | Dx = 1.361 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.075 (3) Å | Cell parameters from 1582 reflections |
b = 11.170 (2) Å | θ = 2.8–22.6° |
c = 9.622 (2) Å | µ = 0.44 mm−1 |
β = 102.945 (4)° | T = 273 K |
V = 1474.3 (6) Å3 | Neddle, colourless |
Z = 4 | 0.12 × 0.10 × 0.06 mm |
Bruker APEXII CCD area-detector diffractometer | 2610 independent reflections |
Radiation source: fine-focus sealed tube | 1803 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
phi and ω scans | θmax = 25.1°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker 2005) | h = −10→16 |
Tmin = 0.951, Tmax = 0.978 | k = −11→13 |
7597 measured reflections | l = −11→11 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0364P)2 + 0.4415P] where P = (Fo2 + 2Fc2)/3 |
2610 reflections | (Δ/σ)max < 0.001 |
172 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C14H17Cl2NO2 | V = 1474.3 (6) Å3 |
Mr = 302.19 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.075 (3) Å | µ = 0.44 mm−1 |
b = 11.170 (2) Å | T = 273 K |
c = 9.622 (2) Å | 0.12 × 0.10 × 0.06 mm |
β = 102.945 (4)° |
Bruker APEXII CCD area-detector diffractometer | 2610 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker 2005) | 1803 reflections with I > 2σ(I) |
Tmin = 0.951, Tmax = 0.978 | Rint = 0.036 |
7597 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.20 e Å−3 |
2610 reflections | Δρmin = −0.23 e Å−3 |
172 parameters |
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. |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.33190 (6) | 0.95724 (6) | 0.17413 (8) | 0.0681 (3) | |
Cl2 | 0.21347 (6) | 0.76080 (8) | −0.02939 (8) | 0.0782 (3) | |
O1 | 0.47634 (12) | 0.86349 (14) | 0.40289 (16) | 0.0446 (4) | |
O2 | 0.65219 (13) | 0.78839 (16) | 0.35750 (16) | 0.0498 (5) | |
N1 | 0.70962 (15) | 0.74309 (18) | 0.5904 (2) | 0.0470 (5) | |
H1 | 0.6959 | 0.7411 | 0.6731 | 0.056* | |
C1 | 0.42841 (18) | 0.7721 (2) | 0.3221 (3) | 0.0399 (6) | |
C2 | 0.35620 (18) | 0.8068 (2) | 0.2056 (3) | 0.0442 (6) | |
C3 | 0.3039 (2) | 0.7195 (3) | 0.1162 (3) | 0.0529 (7) | |
C4 | 0.3240 (2) | 0.5997 (3) | 0.1445 (3) | 0.0628 (8) | |
H4 | 0.2891 | 0.5413 | 0.0852 | 0.075* | |
C5 | 0.3949 (2) | 0.5672 (3) | 0.2594 (3) | 0.0622 (8) | |
H5 | 0.4081 | 0.4864 | 0.2776 | 0.075* | |
C6 | 0.4473 (2) | 0.6517 (2) | 0.3490 (3) | 0.0492 (7) | |
H6 | 0.4952 | 0.6280 | 0.4273 | 0.059* | |
C7 | 0.55203 (18) | 0.8342 (2) | 0.5232 (2) | 0.0443 (6) | |
H7A | 0.5280 | 0.7747 | 0.5804 | 0.053* | |
H7B | 0.5693 | 0.9052 | 0.5815 | 0.053* | |
C8 | 0.64268 (18) | 0.7858 (2) | 0.4814 (2) | 0.0381 (6) | |
C9 | 0.80516 (18) | 0.6994 (2) | 0.5773 (2) | 0.0452 (6) | |
H9 | 0.7997 | 0.6746 | 0.4781 | 0.054* | |
C10 | 0.8334 (2) | 0.5906 (3) | 0.6705 (3) | 0.0676 (9) | |
H10A | 0.7849 | 0.5283 | 0.6421 | 0.081* | |
H10B | 0.8354 | 0.6113 | 0.7690 | 0.081* | |
C11 | 0.9331 (3) | 0.5441 (3) | 0.6577 (4) | 0.0930 (12) | |
H11A | 0.9517 | 0.4775 | 0.7228 | 0.112* | |
H11B | 0.9287 | 0.5147 | 0.5616 | 0.112* | |
C12 | 1.0103 (2) | 0.6389 (4) | 0.6904 (4) | 0.0973 (14) | |
H12A | 1.0712 | 0.6072 | 0.6749 | 0.117* | |
H12B | 1.0203 | 0.6620 | 0.7899 | 0.117* | |
C13 | 0.9811 (3) | 0.7474 (3) | 0.5972 (5) | 0.0927 (12) | |
H13A | 0.9783 | 0.7262 | 0.4986 | 0.111* | |
H13B | 1.0299 | 0.8095 | 0.6243 | 0.111* | |
C14 | 0.8822 (2) | 0.7954 (3) | 0.6107 (4) | 0.0721 (9) | |
H14A | 0.8867 | 0.8246 | 0.7069 | 0.087* | |
H14B | 0.8637 | 0.8621 | 0.5456 | 0.087* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0662 (5) | 0.0580 (5) | 0.0687 (5) | 0.0111 (4) | −0.0087 (4) | 0.0010 (4) |
Cl2 | 0.0465 (5) | 0.1188 (8) | 0.0639 (5) | −0.0105 (4) | 0.0008 (4) | −0.0180 (4) |
O1 | 0.0433 (10) | 0.0408 (10) | 0.0467 (10) | 0.0050 (8) | 0.0037 (8) | −0.0051 (8) |
O2 | 0.0546 (12) | 0.0650 (12) | 0.0331 (9) | 0.0081 (9) | 0.0172 (8) | 0.0044 (8) |
N1 | 0.0395 (12) | 0.0742 (15) | 0.0301 (10) | 0.0093 (11) | 0.0134 (9) | 0.0043 (10) |
C1 | 0.0378 (14) | 0.0418 (15) | 0.0447 (14) | −0.0011 (11) | 0.0190 (12) | −0.0056 (11) |
C2 | 0.0385 (14) | 0.0494 (15) | 0.0471 (14) | −0.0006 (12) | 0.0143 (12) | −0.0050 (12) |
C3 | 0.0413 (15) | 0.072 (2) | 0.0493 (16) | −0.0100 (14) | 0.0171 (13) | −0.0125 (13) |
C4 | 0.0540 (19) | 0.063 (2) | 0.077 (2) | −0.0235 (16) | 0.0271 (17) | −0.0257 (16) |
C5 | 0.065 (2) | 0.0457 (17) | 0.083 (2) | −0.0081 (15) | 0.0309 (18) | −0.0068 (15) |
C6 | 0.0488 (16) | 0.0464 (16) | 0.0572 (16) | −0.0010 (13) | 0.0221 (13) | 0.0010 (13) |
C7 | 0.0431 (15) | 0.0535 (15) | 0.0365 (13) | 0.0059 (12) | 0.0091 (11) | −0.0027 (11) |
C8 | 0.0415 (14) | 0.0389 (13) | 0.0355 (13) | −0.0004 (11) | 0.0122 (11) | −0.0018 (10) |
C9 | 0.0357 (14) | 0.0663 (17) | 0.0349 (13) | 0.0041 (13) | 0.0108 (11) | −0.0024 (12) |
C10 | 0.0514 (19) | 0.082 (2) | 0.074 (2) | 0.0149 (16) | 0.0221 (16) | 0.0184 (17) |
C11 | 0.067 (2) | 0.108 (3) | 0.109 (3) | 0.038 (2) | 0.030 (2) | 0.031 (2) |
C12 | 0.044 (2) | 0.172 (4) | 0.071 (2) | 0.020 (2) | 0.0023 (17) | −0.026 (3) |
C13 | 0.048 (2) | 0.114 (3) | 0.122 (3) | −0.020 (2) | 0.033 (2) | −0.031 (3) |
C14 | 0.055 (2) | 0.073 (2) | 0.093 (2) | −0.0116 (17) | 0.0266 (18) | −0.0106 (17) |
Cl1—C2 | 1.728 (3) | C7—H7B | 0.9700 |
Cl2—C3 | 1.731 (3) | C9—C14 | 1.508 (4) |
O1—C1 | 1.366 (3) | C9—C10 | 1.510 (4) |
O1—C7 | 1.425 (3) | C9—H9 | 0.9800 |
O2—C8 | 1.229 (3) | C10—C11 | 1.527 (4) |
N1—C8 | 1.332 (3) | C10—H10A | 0.9700 |
N1—C9 | 1.462 (3) | C10—H10B | 0.9700 |
N1—H1 | 0.8600 | C11—C12 | 1.499 (5) |
C1—C6 | 1.385 (3) | C11—H11A | 0.9700 |
C1—C2 | 1.389 (4) | C11—H11B | 0.9700 |
C2—C3 | 1.396 (4) | C12—C13 | 1.509 (5) |
C3—C4 | 1.382 (4) | C12—H12A | 0.9700 |
C4—C5 | 1.362 (4) | C12—H12B | 0.9700 |
C4—H4 | 0.9300 | C13—C14 | 1.525 (5) |
C5—C6 | 1.376 (4) | C13—H13A | 0.9700 |
C5—H5 | 0.9300 | C13—H13B | 0.9700 |
C6—H6 | 0.9300 | C14—H14A | 0.9700 |
C7—C8 | 1.521 (3) | C14—H14B | 0.9700 |
C7—H7A | 0.9700 | ||
C1—O1—C7 | 118.35 (19) | N1—C9—H9 | 107.7 |
C8—N1—C9 | 123.64 (19) | C14—C9—H9 | 107.7 |
C8—N1—H1 | 118.2 | C10—C9—H9 | 107.7 |
C9—N1—H1 | 118.2 | C9—C10—C11 | 110.5 (2) |
O1—C1—C6 | 124.8 (2) | C9—C10—H10A | 109.5 |
O1—C1—C2 | 115.5 (2) | C11—C10—H10A | 109.6 |
C6—C1—C2 | 119.8 (2) | C9—C10—H10B | 109.5 |
C1—C2—C3 | 119.5 (2) | C11—C10—H10B | 109.5 |
C1—C2—Cl1 | 119.52 (19) | H10A—C10—H10B | 108.1 |
C3—C2—Cl1 | 121.0 (2) | C12—C11—C10 | 112.2 (3) |
C4—C3—C2 | 119.9 (3) | C12—C11—H11A | 109.2 |
C4—C3—Cl2 | 119.9 (2) | C10—C11—H11A | 109.2 |
C2—C3—Cl2 | 120.2 (2) | C12—C11—H11B | 109.2 |
C5—C4—C3 | 119.9 (3) | C10—C11—H11B | 109.2 |
C5—C4—H4 | 120.1 | H11A—C11—H11B | 107.9 |
C3—C4—H4 | 120.1 | C11—C12—C13 | 110.8 (3) |
C4—C5—C6 | 121.2 (3) | C11—C12—H12A | 109.5 |
C4—C5—H5 | 119.4 | C13—C12—H12A | 109.5 |
C6—C5—H5 | 119.4 | C11—C12—H12B | 109.5 |
C5—C6—C1 | 119.8 (3) | C13—C12—H12B | 109.5 |
C5—C6—H6 | 120.1 | H12A—C12—H12B | 108.1 |
C1—C6—H6 | 120.1 | C12—C13—C14 | 111.3 (3) |
O1—C7—C8 | 112.66 (18) | C12—C13—H13A | 109.4 |
O1—C7—H7A | 109.1 | C14—C13—H13A | 109.4 |
C8—C7—H7A | 109.1 | C12—C13—H13B | 109.4 |
O1—C7—H7B | 109.1 | C14—C13—H13B | 109.4 |
C8—C7—H7B | 109.1 | H13A—C13—H13B | 108.0 |
H7A—C7—H7B | 107.8 | C9—C14—C13 | 111.0 (3) |
O2—C8—N1 | 124.1 (2) | C9—C14—H14A | 109.4 |
O2—C8—C7 | 121.9 (2) | C13—C14—H14A | 109.4 |
N1—C8—C7 | 113.97 (19) | C9—C14—H14B | 109.4 |
N1—C9—C14 | 112.0 (2) | C13—C14—H14B | 109.4 |
N1—C9—C10 | 110.0 (2) | H14A—C14—H14B | 108.0 |
C14—C9—C10 | 111.4 (2) | ||
C7—O1—C1—C6 | 0.6 (3) | C1—O1—C7—C8 | 71.2 (3) |
C7—O1—C1—C2 | −179.4 (2) | C9—N1—C8—O2 | 3.3 (4) |
O1—C1—C2—C3 | 179.5 (2) | C9—N1—C8—C7 | −175.8 (2) |
C6—C1—C2—C3 | −0.5 (4) | O1—C7—C8—O2 | 9.2 (3) |
O1—C1—C2—Cl1 | −1.0 (3) | O1—C7—C8—N1 | −171.7 (2) |
C6—C1—C2—Cl1 | 179.11 (18) | C8—N1—C9—C14 | 93.9 (3) |
C1—C2—C3—C4 | 0.3 (4) | C8—N1—C9—C10 | −141.5 (3) |
Cl1—C2—C3—C4 | −179.3 (2) | N1—C9—C10—C11 | 180.0 (3) |
C1—C2—C3—Cl2 | 179.88 (19) | C14—C9—C10—C11 | −55.1 (4) |
Cl1—C2—C3—Cl2 | 0.3 (3) | C9—C10—C11—C12 | 55.2 (4) |
C2—C3—C4—C5 | −0.1 (4) | C10—C11—C12—C13 | −55.4 (4) |
Cl2—C3—C4—C5 | −179.8 (2) | C11—C12—C13—C14 | 55.4 (4) |
C3—C4—C5—C6 | 0.2 (4) | N1—C9—C14—C13 | 179.7 (3) |
C4—C5—C6—C1 | −0.4 (4) | C10—C9—C14—C13 | 55.9 (4) |
O1—C1—C6—C5 | −179.4 (2) | C12—C13—C14—C9 | −55.8 (4) |
C2—C1—C6—C5 | 0.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 2.03 | 2.883 (3) | 171 |
Symmetry code: (i) x, −y+3/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H17Cl2NO2 |
Mr | 302.19 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 273 |
a, b, c (Å) | 14.075 (3), 11.170 (2), 9.622 (2) |
β (°) | 102.945 (4) |
V (Å3) | 1474.3 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.44 |
Crystal size (mm) | 0.12 × 0.10 × 0.06 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker 2005) |
Tmin, Tmax | 0.951, 0.978 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7597, 2610, 1803 |
Rint | 0.036 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.124, 1.02 |
No. of reflections | 2610 |
No. of parameters | 172 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.23 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 2.03 | 2.883 (3) | 171 |
Symmetry code: (i) x, −y+3/2, z+1/2. |
The structure determination was performed as a part of a project on the interactions of small molecules with proteins. The structures of the similar compounds N-benzyl-2-(2-chloro-4-methylphenoxy)acetamide (Li et al., 2008a) and N-benzyl-2-(2,6-dichlorophenoxy)acetamide (Li et al., 2008b) were reported previously by our group.
In the crystal structure the cyclohexyl ring is in a chair conformation. The molecules are connected via N—H···O hydrogen bonding between the N-H H atom and the carbonyl O atom into chains, that elongate in the direction of the c-axis.