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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808022526/nc2110sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536808022526/nc2110Isup2.hkl
Contains datablock I

CCDC reference: 700602

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.046
  • wR factor = 0.133
  • Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 0 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Related literature top

Please provide related literature.

Experimental top

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 top

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.

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with labelling and displacement ellipsoids drawn at the 50% probability level.
N-Benzyl-2-(2-chloro-4-methylphenoxy)acetamide top
Crystal data top
C16H16ClNO2Dx = 1.335 Mg m3
Mr = 289.75Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 2043 reflections
a = 11.9900 (18) Åθ = 2.9–22.9°
b = 9.2986 (14) ŵ = 0.27 mm1
c = 25.868 (4) ÅT = 273 K
V = 2884.1 (7) Å3Block, colorless
Z = 80.15 × 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 tubeRint = 0.051
Graphite monochromatorθmax = 27.5°, θmin = 1.6°
ϕ and ω scansh = 1515
15831 measured reflectionsk = 1211
3286 independent reflectionsl = 2533
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H 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 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C16H16ClNO2V = 2884.1 (7) Å3
Mr = 289.75Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 11.9900 (18) ŵ = 0.27 mm1
b = 9.2986 (14) ÅT = 273 K
c = 25.868 (4) Å0.15 × 0.10 × 0.10 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1964 reflections with I > 2σ(I)
15831 measured reflectionsRint = 0.051
3286 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.133H atoms treated by a mixture of independent and constrained refinement
S = 0.96Δρmax = 0.21 e Å3
3286 reflectionsΔρmin = 0.22 e Å3
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
xyzUiso*/Ueq
N0.25818 (17)0.4733 (2)0.38688 (7)0.0475 (5)
H0.2699 (18)0.557 (3)0.3929 (9)0.049 (7)*
Cl10.03007 (5)0.17559 (7)0.57574 (3)0.0657 (2)
O10.12962 (13)0.38711 (16)0.50994 (6)0.0518 (4)
O20.19800 (14)0.26379 (16)0.42037 (6)0.0557 (4)
C10.17217 (18)0.2116 (2)0.57204 (8)0.0449 (5)
C20.24535 (19)0.1359 (2)0.60276 (8)0.0479 (5)
H20.21780.06750.62570.057*
C30.35942 (19)0.1599 (2)0.60016 (9)0.0484 (5)
C40.4390 (2)0.0750 (3)0.63326 (10)0.0669 (7)
H4A0.51400.10530.62630.100*
H4B0.43150.02550.62550.100*
H4C0.42210.09110.66910.100*
C50.3965 (2)0.2623 (3)0.56529 (9)0.0518 (6)
H50.47260.28030.56260.062*
C60.32366 (19)0.3384 (2)0.53445 (9)0.0498 (6)
H60.35140.40620.51130.060*
C70.20977 (18)0.3153 (2)0.53747 (8)0.0431 (5)
C80.1658 (2)0.4792 (2)0.46959 (8)0.0510 (6)
H8A0.22390.54220.48250.061*
H8B0.10380.53870.45840.061*
C90.21020 (18)0.3948 (2)0.42362 (8)0.0428 (5)
C100.2954 (2)0.4080 (2)0.33864 (8)0.0510 (6)
H10A0.23650.34730.32500.061*
H10B0.35970.34770.34540.061*
C110.32561 (18)0.5196 (2)0.29900 (8)0.0441 (5)
C120.2495 (2)0.5609 (2)0.26193 (9)0.0547 (6)
H120.17870.52010.26190.066*
C130.2765 (2)0.6617 (3)0.22488 (10)0.0653 (7)
H130.22410.68800.20010.078*
C140.3801 (2)0.7230 (3)0.22441 (10)0.0655 (7)
H140.39850.79010.19910.079*
C150.4562 (2)0.6855 (3)0.26101 (12)0.0686 (7)
H150.52630.72820.26110.082*
C160.4294 (2)0.5832 (3)0.29846 (10)0.0608 (7)
H160.48200.55770.32320.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N0.0699 (13)0.0305 (10)0.0421 (10)0.0025 (9)0.0022 (9)0.0059 (8)
Cl10.0507 (4)0.0739 (5)0.0724 (5)0.0075 (3)0.0088 (3)0.0085 (3)
O10.0589 (10)0.0498 (9)0.0468 (9)0.0051 (8)0.0059 (7)0.0039 (7)
O20.0827 (12)0.0299 (8)0.0546 (10)0.0008 (8)0.0042 (8)0.0021 (7)
C10.0479 (12)0.0466 (12)0.0403 (12)0.0045 (10)0.0084 (10)0.0056 (10)
C20.0601 (14)0.0441 (12)0.0393 (11)0.0043 (11)0.0071 (11)0.0013 (10)
C30.0573 (14)0.0465 (13)0.0413 (12)0.0001 (11)0.0005 (10)0.0075 (10)
C40.0665 (16)0.0714 (17)0.0627 (16)0.0036 (14)0.0056 (13)0.0011 (14)
C50.0480 (13)0.0502 (14)0.0572 (14)0.0033 (11)0.0017 (11)0.0088 (11)
C60.0588 (14)0.0441 (12)0.0465 (13)0.0063 (11)0.0104 (11)0.0021 (10)
C70.0525 (13)0.0409 (11)0.0360 (11)0.0006 (10)0.0058 (9)0.0072 (9)
C80.0690 (15)0.0373 (11)0.0468 (13)0.0048 (11)0.0035 (11)0.0006 (10)
C90.0546 (13)0.0341 (11)0.0397 (12)0.0046 (9)0.0050 (10)0.0012 (9)
C100.0690 (15)0.0424 (12)0.0414 (12)0.0060 (11)0.0006 (11)0.0038 (10)
C110.0501 (13)0.0410 (11)0.0410 (12)0.0054 (10)0.0032 (10)0.0050 (9)
C120.0540 (14)0.0569 (14)0.0531 (14)0.0011 (12)0.0045 (11)0.0017 (11)
C130.0795 (19)0.0671 (16)0.0494 (14)0.0046 (14)0.0054 (13)0.0077 (13)
C140.084 (2)0.0584 (16)0.0541 (16)0.0035 (14)0.0201 (15)0.0046 (12)
C150.0574 (16)0.0654 (17)0.083 (2)0.0106 (13)0.0191 (14)0.0030 (15)
C160.0523 (14)0.0636 (16)0.0665 (17)0.0048 (12)0.0075 (12)0.0037 (13)
Geometric parameters (Å, º) top
N—C91.329 (3)C6—H60.9300
N—C101.458 (3)C8—C91.521 (3)
N—H0.80 (2)C8—H8A0.9700
Cl1—C11.739 (2)C8—H8B0.9700
O1—C71.370 (3)C10—C111.503 (3)
O1—C81.418 (3)C10—H10A0.9700
O2—C91.230 (2)C10—H10B0.9700
C1—C21.377 (3)C11—C161.378 (3)
C1—C71.390 (3)C11—C121.378 (3)
C2—C31.387 (3)C12—C131.380 (3)
C2—H20.9300C12—H120.9300
C3—C51.385 (3)C13—C141.366 (4)
C3—C41.505 (3)C13—H130.9300
C4—H4A0.9600C14—C151.361 (4)
C4—H4B0.9600C14—H140.9300
C4—H4C0.9600C15—C161.395 (4)
C5—C61.378 (3)C15—H150.9300
C5—H50.9300C16—H160.9300
C6—C71.385 (3)
C9—N—C10121.07 (19)O1—C8—H8B109.3
C9—N—H117.9 (16)C9—C8—H8B109.3
C10—N—H120.9 (16)H8A—C8—H8B107.9
C7—O1—C8117.56 (17)O2—C9—N123.1 (2)
C2—C1—C7121.3 (2)O2—C9—C8121.51 (19)
C2—C1—Cl1119.61 (17)N—C9—C8115.30 (18)
C7—C1—Cl1119.12 (17)N—C10—C11111.74 (17)
C1—C2—C3121.2 (2)N—C10—H10A109.3
C1—C2—H2119.4C11—C10—H10A109.3
C3—C2—H2119.4N—C10—H10B109.3
C2—C3—C5117.3 (2)C11—C10—H10B109.3
C2—C3—C4120.9 (2)H10A—C10—H10B107.9
C5—C3—C4121.8 (2)C16—C11—C12118.1 (2)
C3—C4—H4A109.5C16—C11—C10121.4 (2)
C3—C4—H4B109.5C12—C11—C10120.5 (2)
H4A—C4—H4B109.5C11—C12—C13121.1 (2)
C3—C4—H4C109.5C11—C12—H12119.4
H4A—C4—H4C109.5C13—C12—H12119.4
H4B—C4—H4C109.5C14—C13—C12120.2 (3)
C6—C5—C3121.8 (2)C14—C13—H13119.9
C6—C5—H5119.1C12—C13—H13119.9
C3—C5—H5119.1C15—C14—C13119.8 (2)
C5—C6—C7120.8 (2)C15—C14—H14120.1
C5—C6—H6119.6C13—C14—H14120.1
C7—C6—H6119.6C14—C15—C16120.2 (2)
O1—C7—C6125.9 (2)C14—C15—H15119.9
O1—C7—C1116.42 (19)C16—C15—H15119.9
C6—C7—C1117.6 (2)C11—C16—C15120.5 (2)
O1—C8—C9111.79 (17)C11—C16—H16119.8
O1—C8—H8A109.3C15—C16—H16119.8
C9—C8—H8A109.3
C7—C1—C2—C30.3 (3)C10—N—C9—O22.8 (3)
Cl1—C1—C2—C3178.82 (16)C10—N—C9—C8174.4 (2)
C1—C2—C3—C50.3 (3)O1—C8—C9—O210.6 (3)
C1—C2—C3—C4179.0 (2)O1—C8—C9—N172.11 (19)
C2—C3—C5—C60.3 (3)C9—N—C10—C11168.6 (2)
C4—C3—C5—C6179.0 (2)N—C10—C11—C1683.7 (3)
C3—C5—C6—C70.3 (3)N—C10—C11—C1296.4 (2)
C8—O1—C7—C69.4 (3)C16—C11—C12—C130.8 (3)
C8—O1—C7—C1171.68 (17)C10—C11—C12—C13179.1 (2)
C5—C6—C7—O1178.02 (19)C11—C12—C13—C140.1 (4)
C5—C6—C7—C10.9 (3)C12—C13—C14—C150.8 (4)
C2—C1—C7—O1178.11 (18)C13—C14—C15—C161.0 (4)
Cl1—C1—C7—O12.7 (2)C12—C11—C16—C150.5 (3)
C2—C1—C7—C60.9 (3)C10—C11—C16—C15179.4 (2)
Cl1—C1—C7—C6178.22 (16)C14—C15—C16—C110.4 (4)
C7—O1—C8—C971.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N—H···O2i0.80 (2)2.09 (3)2.885 (2)169 (2)
Symmetry code: (i) x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC16H16ClNO2
Mr289.75
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)273
a, b, c (Å)11.9900 (18), 9.2986 (14), 25.868 (4)
V3)2884.1 (7)
Z8
Radiation typeMo Kα
µ (mm1)0.27
Crystal size (mm)0.15 × 0.10 × 0.10
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
15831, 3286, 1964
Rint0.051
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.133, 0.96
No. of reflections3286
No. of parameters185
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.21, 0.22

Computer programs: APEX2 [or SMART?] (Bruker, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N—H···O2i0.80 (2)2.09 (3)2.885 (2)169 (2)
Symmetry code: (i) x+1/2, y+1/2, z.
 

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