The structure determination of the title compound, C
16H
16ClNO
2, was performed as part of a project on the interactions between small organic molecules and proteins. In the crystal structure, the dihedral angle between the two aromatic rings is 16.14 (12)°. The molecules are connected via N—H

O hydrogen bonding into chains, which extend in the direction of the
b axis.
Supporting information
CCDC reference: 700602
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.046
- wR factor = 0.133
- Data-to-parameter ratio = 17.8
checkCIF/PLATON results
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A solution of 2-chloro-4-methylphenol (1.0 mmol),
N-benzyl-2-chloroacetamide (1.1 mmol), K2CO3 (1.1 mmol) in CH3CN
(20 ml) was refluxed for 3 h. Afterwards the mixture has cooled down to room
temperature the solvent was evaporated under reduced pressure. The residue was
poured into water and adjusted the pH 6–7. The aqueous phase was extracted
with
ethyl acetate, washed with brine and dried over anhydrous MgSO4.
Finally the product was purified by column chromatography on silica gel.
Crystals of (I) suitable for X-ray diffraction were obtained by
cooling of a solution of the title compound in a mixture of ethylacetate
and hexane.
All C-H atoms were placed in geometrically calculated positions and refined
using a riding model with C—H = 0.97 Å (for CH2 groups) and 0.96 Å
(for CH3 groups), their isotropic displacement parameters were set to 1.2
times (1.5 times for CH3 groups) the equivalent displacement parameter of
their parent atoms. The N-H H atom was freely refined.
Data collection: APEX2 [or SMART?] (Bruker, 2005); cell refinement: APEX2 [or SMART?] (Bruker, 2005); data reduction: APEX2 [or SMART?] (Bruker, 2005); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).
N-Benzyl-2-(2-chloro-4-methylphenoxy)acetamide
top
Crystal data top
C16H16ClNO2 | Dx = 1.335 Mg m−3 |
Mr = 289.75 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 2043 reflections |
a = 11.9900 (18) Å | θ = 2.9–22.9° |
b = 9.2986 (14) Å | µ = 0.27 mm−1 |
c = 25.868 (4) Å | T = 273 K |
V = 2884.1 (7) Å3 | Block, colorless |
Z = 8 | 0.15 × 0.10 × 0.10 mm |
F(000) = 1216 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1964 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.051 |
Graphite monochromator | θmax = 27.5°, θmin = 1.6° |
ϕ and ω scans | h = −15→15 |
15831 measured reflections | k = −12→11 |
3286 independent reflections | l = −25→33 |
Refinement top
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | w = 1/[σ2(Fo2) + (0.06P)2 + 0.774P] where P = (Fo2 + 2Fc2)/3 |
3286 reflections | (Δ/σ)max < 0.001 |
185 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Crystal data top
C16H16ClNO2 | V = 2884.1 (7) Å3 |
Mr = 289.75 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 11.9900 (18) Å | µ = 0.27 mm−1 |
b = 9.2986 (14) Å | T = 273 K |
c = 25.868 (4) Å | 0.15 × 0.10 × 0.10 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1964 reflections with I > 2σ(I) |
15831 measured reflections | Rint = 0.051 |
3286 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.133 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | Δρmax = 0.21 e Å−3 |
3286 reflections | Δρmin = −0.22 e Å−3 |
185 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N | 0.25818 (17) | 0.4733 (2) | 0.38688 (7) | 0.0475 (5) | |
H | 0.2699 (18) | 0.557 (3) | 0.3929 (9) | 0.049 (7)* | |
Cl1 | 0.03007 (5) | 0.17559 (7) | 0.57574 (3) | 0.0657 (2) | |
O1 | 0.12962 (13) | 0.38711 (16) | 0.50994 (6) | 0.0518 (4) | |
O2 | 0.19800 (14) | 0.26379 (16) | 0.42037 (6) | 0.0557 (4) | |
C1 | 0.17217 (18) | 0.2116 (2) | 0.57204 (8) | 0.0449 (5) | |
C2 | 0.24535 (19) | 0.1359 (2) | 0.60276 (8) | 0.0479 (5) | |
H2 | 0.2178 | 0.0675 | 0.6257 | 0.057* | |
C3 | 0.35942 (19) | 0.1599 (2) | 0.60016 (9) | 0.0484 (5) | |
C4 | 0.4390 (2) | 0.0750 (3) | 0.63326 (10) | 0.0669 (7) | |
H4A | 0.5140 | 0.1053 | 0.6263 | 0.100* | |
H4B | 0.4315 | −0.0255 | 0.6255 | 0.100* | |
H4C | 0.4221 | 0.0911 | 0.6691 | 0.100* | |
C5 | 0.3965 (2) | 0.2623 (3) | 0.56529 (9) | 0.0518 (6) | |
H5 | 0.4726 | 0.2803 | 0.5626 | 0.062* | |
C6 | 0.32366 (19) | 0.3384 (2) | 0.53445 (9) | 0.0498 (6) | |
H6 | 0.3514 | 0.4062 | 0.5113 | 0.060* | |
C7 | 0.20977 (18) | 0.3153 (2) | 0.53747 (8) | 0.0431 (5) | |
C8 | 0.1658 (2) | 0.4792 (2) | 0.46959 (8) | 0.0510 (6) | |
H8A | 0.2239 | 0.5422 | 0.4825 | 0.061* | |
H8B | 0.1038 | 0.5387 | 0.4584 | 0.061* | |
C9 | 0.21020 (18) | 0.3948 (2) | 0.42362 (8) | 0.0428 (5) | |
C10 | 0.2954 (2) | 0.4080 (2) | 0.33864 (8) | 0.0510 (6) | |
H10A | 0.2365 | 0.3473 | 0.3250 | 0.061* | |
H10B | 0.3597 | 0.3477 | 0.3454 | 0.061* | |
C11 | 0.32561 (18) | 0.5196 (2) | 0.29900 (8) | 0.0441 (5) | |
C12 | 0.2495 (2) | 0.5609 (2) | 0.26193 (9) | 0.0547 (6) | |
H12 | 0.1787 | 0.5201 | 0.2619 | 0.066* | |
C13 | 0.2765 (2) | 0.6617 (3) | 0.22488 (10) | 0.0653 (7) | |
H13 | 0.2241 | 0.6880 | 0.2001 | 0.078* | |
C14 | 0.3801 (2) | 0.7230 (3) | 0.22441 (10) | 0.0655 (7) | |
H14 | 0.3985 | 0.7901 | 0.1991 | 0.079* | |
C15 | 0.4562 (2) | 0.6855 (3) | 0.26101 (12) | 0.0686 (7) | |
H15 | 0.5263 | 0.7282 | 0.2611 | 0.082* | |
C16 | 0.4294 (2) | 0.5832 (3) | 0.29846 (10) | 0.0608 (7) | |
H16 | 0.4820 | 0.5577 | 0.3232 | 0.073* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N | 0.0699 (13) | 0.0305 (10) | 0.0421 (10) | −0.0025 (9) | 0.0022 (9) | −0.0059 (8) |
Cl1 | 0.0507 (4) | 0.0739 (5) | 0.0724 (5) | −0.0075 (3) | 0.0088 (3) | 0.0085 (3) |
O1 | 0.0589 (10) | 0.0498 (9) | 0.0468 (9) | 0.0051 (8) | 0.0059 (7) | 0.0039 (7) |
O2 | 0.0827 (12) | 0.0299 (8) | 0.0546 (10) | 0.0008 (8) | 0.0042 (8) | −0.0021 (7) |
C1 | 0.0479 (12) | 0.0466 (12) | 0.0403 (12) | −0.0045 (10) | 0.0084 (10) | −0.0056 (10) |
C2 | 0.0601 (14) | 0.0441 (12) | 0.0393 (11) | −0.0043 (11) | 0.0071 (11) | −0.0013 (10) |
C3 | 0.0573 (14) | 0.0465 (13) | 0.0413 (12) | 0.0001 (11) | 0.0005 (10) | −0.0075 (10) |
C4 | 0.0665 (16) | 0.0714 (17) | 0.0627 (16) | 0.0036 (14) | −0.0056 (13) | 0.0011 (14) |
C5 | 0.0480 (13) | 0.0502 (14) | 0.0572 (14) | −0.0033 (11) | 0.0017 (11) | −0.0088 (11) |
C6 | 0.0588 (14) | 0.0441 (12) | 0.0465 (13) | −0.0063 (11) | 0.0104 (11) | −0.0021 (10) |
C7 | 0.0525 (13) | 0.0409 (11) | 0.0360 (11) | −0.0006 (10) | 0.0058 (9) | −0.0072 (9) |
C8 | 0.0690 (15) | 0.0373 (11) | 0.0468 (13) | 0.0048 (11) | 0.0035 (11) | 0.0006 (10) |
C9 | 0.0546 (13) | 0.0341 (11) | 0.0397 (12) | 0.0046 (9) | −0.0050 (10) | 0.0012 (9) |
C10 | 0.0690 (15) | 0.0424 (12) | 0.0414 (12) | 0.0060 (11) | −0.0006 (11) | −0.0038 (10) |
C11 | 0.0501 (13) | 0.0410 (11) | 0.0410 (12) | 0.0054 (10) | 0.0032 (10) | −0.0050 (9) |
C12 | 0.0540 (14) | 0.0569 (14) | 0.0531 (14) | −0.0011 (12) | −0.0045 (11) | 0.0017 (11) |
C13 | 0.0795 (19) | 0.0671 (16) | 0.0494 (14) | 0.0046 (14) | −0.0054 (13) | 0.0077 (13) |
C14 | 0.084 (2) | 0.0584 (16) | 0.0541 (16) | 0.0035 (14) | 0.0201 (15) | 0.0046 (12) |
C15 | 0.0574 (16) | 0.0654 (17) | 0.083 (2) | −0.0106 (13) | 0.0191 (14) | −0.0030 (15) |
C16 | 0.0523 (14) | 0.0636 (16) | 0.0665 (17) | 0.0048 (12) | −0.0075 (12) | −0.0037 (13) |
Geometric parameters (Å, º) top
N—C9 | 1.329 (3) | C6—H6 | 0.9300 |
N—C10 | 1.458 (3) | C8—C9 | 1.521 (3) |
N—H | 0.80 (2) | C8—H8A | 0.9700 |
Cl1—C1 | 1.739 (2) | C8—H8B | 0.9700 |
O1—C7 | 1.370 (3) | C10—C11 | 1.503 (3) |
O1—C8 | 1.418 (3) | C10—H10A | 0.9700 |
O2—C9 | 1.230 (2) | C10—H10B | 0.9700 |
C1—C2 | 1.377 (3) | C11—C16 | 1.378 (3) |
C1—C7 | 1.390 (3) | C11—C12 | 1.378 (3) |
C2—C3 | 1.387 (3) | C12—C13 | 1.380 (3) |
C2—H2 | 0.9300 | C12—H12 | 0.9300 |
C3—C5 | 1.385 (3) | C13—C14 | 1.366 (4) |
C3—C4 | 1.505 (3) | C13—H13 | 0.9300 |
C4—H4A | 0.9600 | C14—C15 | 1.361 (4) |
C4—H4B | 0.9600 | C14—H14 | 0.9300 |
C4—H4C | 0.9600 | C15—C16 | 1.395 (4) |
C5—C6 | 1.378 (3) | C15—H15 | 0.9300 |
C5—H5 | 0.9300 | C16—H16 | 0.9300 |
C6—C7 | 1.385 (3) | | |
| | | |
C9—N—C10 | 121.07 (19) | O1—C8—H8B | 109.3 |
C9—N—H | 117.9 (16) | C9—C8—H8B | 109.3 |
C10—N—H | 120.9 (16) | H8A—C8—H8B | 107.9 |
C7—O1—C8 | 117.56 (17) | O2—C9—N | 123.1 (2) |
C2—C1—C7 | 121.3 (2) | O2—C9—C8 | 121.51 (19) |
C2—C1—Cl1 | 119.61 (17) | N—C9—C8 | 115.30 (18) |
C7—C1—Cl1 | 119.12 (17) | N—C10—C11 | 111.74 (17) |
C1—C2—C3 | 121.2 (2) | N—C10—H10A | 109.3 |
C1—C2—H2 | 119.4 | C11—C10—H10A | 109.3 |
C3—C2—H2 | 119.4 | N—C10—H10B | 109.3 |
C2—C3—C5 | 117.3 (2) | C11—C10—H10B | 109.3 |
C2—C3—C4 | 120.9 (2) | H10A—C10—H10B | 107.9 |
C5—C3—C4 | 121.8 (2) | C16—C11—C12 | 118.1 (2) |
C3—C4—H4A | 109.5 | C16—C11—C10 | 121.4 (2) |
C3—C4—H4B | 109.5 | C12—C11—C10 | 120.5 (2) |
H4A—C4—H4B | 109.5 | C11—C12—C13 | 121.1 (2) |
C3—C4—H4C | 109.5 | C11—C12—H12 | 119.4 |
H4A—C4—H4C | 109.5 | C13—C12—H12 | 119.4 |
H4B—C4—H4C | 109.5 | C14—C13—C12 | 120.2 (3) |
C6—C5—C3 | 121.8 (2) | C14—C13—H13 | 119.9 |
C6—C5—H5 | 119.1 | C12—C13—H13 | 119.9 |
C3—C5—H5 | 119.1 | C15—C14—C13 | 119.8 (2) |
C5—C6—C7 | 120.8 (2) | C15—C14—H14 | 120.1 |
C5—C6—H6 | 119.6 | C13—C14—H14 | 120.1 |
C7—C6—H6 | 119.6 | C14—C15—C16 | 120.2 (2) |
O1—C7—C6 | 125.9 (2) | C14—C15—H15 | 119.9 |
O1—C7—C1 | 116.42 (19) | C16—C15—H15 | 119.9 |
C6—C7—C1 | 117.6 (2) | C11—C16—C15 | 120.5 (2) |
O1—C8—C9 | 111.79 (17) | C11—C16—H16 | 119.8 |
O1—C8—H8A | 109.3 | C15—C16—H16 | 119.8 |
C9—C8—H8A | 109.3 | | |
| | | |
C7—C1—C2—C3 | −0.3 (3) | C10—N—C9—O2 | 2.8 (3) |
Cl1—C1—C2—C3 | 178.82 (16) | C10—N—C9—C8 | −174.4 (2) |
C1—C2—C3—C5 | −0.3 (3) | O1—C8—C9—O2 | 10.6 (3) |
C1—C2—C3—C4 | −179.0 (2) | O1—C8—C9—N | −172.11 (19) |
C2—C3—C5—C6 | 0.3 (3) | C9—N—C10—C11 | 168.6 (2) |
C4—C3—C5—C6 | 179.0 (2) | N—C10—C11—C16 | 83.7 (3) |
C3—C5—C6—C7 | 0.3 (3) | N—C10—C11—C12 | −96.4 (2) |
C8—O1—C7—C6 | 9.4 (3) | C16—C11—C12—C13 | 0.8 (3) |
C8—O1—C7—C1 | −171.68 (17) | C10—C11—C12—C13 | −179.1 (2) |
C5—C6—C7—O1 | 178.02 (19) | C11—C12—C13—C14 | −0.1 (4) |
C5—C6—C7—C1 | −0.9 (3) | C12—C13—C14—C15 | −0.8 (4) |
C2—C1—C7—O1 | −178.11 (18) | C13—C14—C15—C16 | 1.0 (4) |
Cl1—C1—C7—O1 | 2.7 (2) | C12—C11—C16—C15 | −0.5 (3) |
C2—C1—C7—C6 | 0.9 (3) | C10—C11—C16—C15 | 179.4 (2) |
Cl1—C1—C7—C6 | −178.22 (16) | C14—C15—C16—C11 | −0.4 (4) |
C7—O1—C8—C9 | 71.4 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N—H···O2i | 0.80 (2) | 2.09 (3) | 2.885 (2) | 169 (2) |
Symmetry code: (i) −x+1/2, y+1/2, z. |
Experimental details
Crystal data |
Chemical formula | C16H16ClNO2 |
Mr | 289.75 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 273 |
a, b, c (Å) | 11.9900 (18), 9.2986 (14), 25.868 (4) |
V (Å3) | 2884.1 (7) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.27 |
Crystal size (mm) | 0.15 × 0.10 × 0.10 |
|
Data collection |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15831, 3286, 1964 |
Rint | 0.051 |
(sin θ/λ)max (Å−1) | 0.649 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.133, 0.96 |
No. of reflections | 3286 |
No. of parameters | 185 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.21, −0.22 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N—H···O2i | 0.80 (2) | 2.09 (3) | 2.885 (2) | 169 (2) |
Symmetry code: (i) −x+1/2, y+1/2, z. |