Abstract
The structure determination of the title compound, C16H16ClNO2, 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.
Experimental
Crystal data
C16H16ClNO2
M r = 289.75
Orthorhombic,
a = 11.9900 (18) Å
b = 9.2986 (14) Å
c = 25.868 (4) Å
V = 2884.1 (7) Å3
Z = 8
Mo Kα radiation
μ = 0.27 mm−1
T = 273 (2) K
0.15 × 0.10 × 0.10 mm
Data collection
Bruker APEXII CCD area-detector diffractometer
Absorption correction: none
15831 measured reflections
3286 independent reflections
1964 reflections with I > 2σ(I)
R int = 0.051
Refinement
R[F 2 > 2σ(F 2)] = 0.045
wR(F 2) = 0.133
S = 0.96
3286 reflections
185 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρmax = 0.21 e Å−3
Δρmin = −0.22 e Å−3
Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: APEX2; 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 ▶).
Supplementary Material
Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022526/nc2110sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022526/nc2110Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Table 1. Hydrogen-bond geometry (Å, °).
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) .
Acknowledgments
This study was supported by the Key Project of the Municipal Natural Science Foundation of Chongqing, China (grant No. CSTC, 2008 A A1001).
supplementary crystallographic information
Experimental
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.
Refinement
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.
Figures
Fig. 1.
The molecular structure of (I) with labelling and displacement ellipsoids drawn at the 50% probability level.
Crystal data
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 = 2.9–22.9º |
b = 9.2986 (14) Å | µ = 0.27 mm−1 |
c = 25.868 (4) Å | T = 273 (2) K |
V = 2884.1 (7) Å3 | Block, colorless |
Z = 8 | 0.15 × 0.10 × 0.10 mm |
F000 = 1216 |
Data collection
Bruker SMART CCD area-detector diffractometer | 1964 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.051 |
Monochromator: graphite | θmax = 27.5º |
T = 273(2) K | θmin = 1.6º |
φ and ω scans | h = −15→15 |
Absorption correction: none | k = −12→11 |
15831 measured reflections | l = −25→33 |
3286 independent reflections |
Refinement
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.046 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.133 | w = 1/[σ2(Fo2) + (0.06P)2 + 0.774P] where P = (Fo2 + 2Fc2)/3 |
S = 0.96 | (Δ/σ)max < 0.001 |
3286 reflections | Δρmax = 0.21 e Å−3 |
185 parameters | Δρmin = −0.22 e Å−3 |
Primary atom site location: structure-invariant direct methods | Extinction correction: none |
Special details
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)
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)
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, °)
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, °)
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 codes: (i) −x+1/2, y+1/2, z.
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2110).
References
- Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst.32, 115–119.
- Bruker (2005). APEX2 Bruker AXS Inc., Madison, Wisconsin, USA.
- Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
- Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022526/nc2110sup1.cif
Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022526/nc2110Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report