2-Chloro-N-(4-ethoxy­phen­yl)­acetamide

In the mol­ecule of the title compound, C₁₀H₁₂ClNO₂, an intra­molecular C—H...O hydrogen bond forms a non-planar six-membered ring. In the crystal structure, the mol­ecules are linked by inter­molecular N—H...O hydrogen bonds, forming infinite chains along the c axis. The packing is further stabilized by C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.040
• wR factor = 0.101
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

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   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

N-(4-Ethoxyphenyl)-2-chloroacetamide

Crystal data

C10H12ClNO2	F(000) = 448
Mr = 213.66	Dx = 1.373 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2056 reflections
a = 11.3149 (13) Å	θ = 2.7–25.1°
b = 10.0120 (12) Å	µ = 0.34 mm^−1
c = 9.1966 (11) Å	T = 294 K
β = 97.155 (2)°	Block, colorless
V = 1033.7 (2) Å^3	0.31 × 0.25 × 0.10 mm
Z = 4

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	2027 independent reflections
Radiation source: fine-focus sealed tube	1715 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 8.33 pixels mm^-1	θmax = 26.0°, θmin = 1.8°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→9
Tmin = 0.901, Tmax = 0.967	l = −11→9
5631 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.102	w = 1/[σ^2(Fo^2) + (0.0485P)^2 + 0.351P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
2027 reflections	Δρmax = 0.16 e Å^−3
127 parameters	Δρmin = −0.24 e Å^−3
0 restraints	Absolute structure: Flack (1983), with 1308 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.09 (11)

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.39904 (5)	0.40770 (5)	0.11532 (6)	0.0555 (2)
O1	0.57690 (12)	0.19058 (14)	0.18059 (13)	0.0497 (4)
O2	0.95454 (12)	−0.23321 (15)	−0.06892 (17)	0.0606 (4)
N1	0.59618 (13)	0.14633 (15)	−0.05723 (15)	0.0383 (4)
H1A	0.5686	0.1704	−0.1447	0.046*
C1	0.43727 (16)	0.28680 (18)	−0.0106 (2)	0.0408 (4)
H1B	0.3700	0.2276	−0.0359	0.049*
H1C	0.4539	0.3313	−0.0995	0.049*
C2	0.54491 (15)	0.20471 (16)	0.05011 (18)	0.0330 (4)
C3	0.68928 (14)	0.05066 (17)	−0.04774 (18)	0.0344 (4)
C4	0.75861 (15)	0.01403 (18)	0.08039 (19)	0.0387 (4)
H4A	0.7449	0.0525	0.1688	0.046*
C5	0.84905 (16)	−0.08042 (18)	0.0780 (2)	0.0415 (4)
H5A	0.8955	−0.1044	0.1647	0.050*
C6	0.86992 (16)	−0.13861 (19)	−0.0531 (2)	0.0437 (4)
C7	0.79983 (17)	−0.1006 (2)	−0.1819 (2)	0.0486 (5)
H7A	0.8133	−0.1388	−0.2705	0.058*
C8	0.71139 (16)	−0.00747 (19)	−0.1796 (2)	0.0419 (4)
H8A	0.6657	0.0172	−0.2666	0.050*
C9	1.04211 (17)	−0.2600 (2)	0.0522 (2)	0.0513 (5)
H9A	1.0056	−0.3003	0.1315	0.062*
H9B	1.0811	−0.1779	0.0877	0.062*
C10	1.1310 (2)	−0.3546 (3)	−0.0011 (3)	0.0688 (7)
H10A	1.1917	−0.3755	0.0781	0.103*
H10B	1.1667	−0.3134	−0.0792	0.103*
H10C	1.0912	−0.4352	−0.0362	0.103*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0585 (3)	0.0579 (3)	0.0510 (3)	0.0207 (2)	0.0100 (2)	−0.0086 (2)
O1	0.0620 (9)	0.0597 (9)	0.0270 (7)	0.0198 (7)	0.0038 (6)	−0.0033 (6)
O2	0.0484 (8)	0.0665 (10)	0.0637 (9)	0.0204 (7)	−0.0052 (7)	−0.0196 (8)
N1	0.0429 (8)	0.0475 (9)	0.0245 (7)	0.0083 (7)	0.0039 (6)	0.0010 (6)
C1	0.0434 (10)	0.0421 (10)	0.0364 (9)	0.0052 (8)	0.0033 (8)	−0.0045 (8)
C2	0.0370 (9)	0.0330 (9)	0.0296 (9)	−0.0026 (7)	0.0063 (7)	−0.0010 (7)
C3	0.0341 (9)	0.0377 (9)	0.0318 (9)	−0.0003 (7)	0.0067 (7)	−0.0007 (7)
C4	0.0414 (9)	0.0442 (10)	0.0312 (9)	−0.0004 (8)	0.0070 (7)	−0.0015 (8)
C5	0.0387 (9)	0.0465 (11)	0.0382 (10)	0.0012 (8)	0.0003 (8)	0.0015 (8)
C6	0.0351 (9)	0.0447 (10)	0.0510 (11)	0.0032 (8)	0.0037 (8)	−0.0088 (9)
C7	0.0451 (11)	0.0606 (13)	0.0403 (11)	0.0055 (9)	0.0055 (8)	−0.0173 (9)
C8	0.0403 (10)	0.0527 (11)	0.0320 (9)	0.0025 (8)	0.0014 (7)	−0.0071 (8)
C9	0.0432 (10)	0.0549 (12)	0.0564 (12)	0.0064 (9)	0.0085 (9)	0.0081 (10)
C10	0.0546 (13)	0.0681 (15)	0.0839 (17)	0.0192 (12)	0.0094 (12)	0.0063 (13)

Geometric parameters (Å, º)

Cl1—C1	1.7656 (18)	C4—H4A	0.9300
O1—C2	1.218 (2)	C5—C6	1.386 (3)
O2—C6	1.367 (2)	C5—H5A	0.9300
O2—C9	1.421 (2)	C6—C7	1.394 (3)
N1—C2	1.340 (2)	C7—C8	1.370 (3)
N1—C3	1.418 (2)	C7—H7A	0.9300
N1—H1A	0.8600	C8—H8A	0.9300
C1—C2	1.517 (2)	C9—C10	1.507 (3)
C1—H1B	0.9700	C9—H9A	0.9700
C1—H1C	0.9700	C9—H9B	0.9700
C3—C4	1.381 (2)	C10—H10A	0.9600
C3—C8	1.396 (2)	C10—H10B	0.9600
C4—C5	1.396 (2)	C10—H10C	0.9600
C6—O2—C9	118.48 (16)	O2—C6—C5	125.52 (18)
C2—N1—C3	129.47 (14)	O2—C6—C7	115.52 (17)
C2—N1—H1A	115.3	C5—C6—C7	118.95 (17)
C3—N1—H1A	115.3	C8—C7—C6	120.80 (17)
C2—C1—Cl1	112.42 (12)	C8—C7—H7A	119.6
C2—C1—H1B	109.1	C6—C7—H7A	119.6
Cl1—C1—H1B	109.1	C7—C8—C3	120.53 (17)
C2—C1—H1C	109.1	C7—C8—H8A	119.7
Cl1—C1—H1C	109.1	C3—C8—H8A	119.7
H1B—C1—H1C	107.9	O2—C9—C10	106.99 (18)
O1—C2—N1	124.92 (16)	O2—C9—H9A	110.3
O1—C2—C1	123.50 (15)	C10—C9—H9A	110.3
N1—C2—C1	111.52 (14)	O2—C9—H9B	110.3
C4—C3—C8	119.10 (16)	C10—C9—H9B	110.3
C4—C3—N1	124.77 (15)	H9A—C9—H9B	108.6
C8—C3—N1	116.13 (15)	C9—C10—H10A	109.5
C3—C4—C5	120.41 (17)	C9—C10—H10B	109.5
C3—C4—H4A	119.8	H10A—C10—H10B	109.5
C5—C4—H4A	119.8	C9—C10—H10C	109.5
C6—C5—C4	120.21 (17)	H10A—C10—H10C	109.5
C6—C5—H5A	119.9	H10B—C10—H10C	109.5
C4—C5—H5A	119.9
C3—N1—C2—O1	5.2 (3)	C9—O2—C6—C7	169.33 (18)
C3—N1—C2—C1	−172.18 (17)	C4—C5—C6—O2	−179.08 (18)
Cl1—C1—C2—O1	22.9 (2)	C4—C5—C6—C7	0.4 (3)
Cl1—C1—C2—N1	−159.62 (13)	O2—C6—C7—C8	179.38 (18)
C2—N1—C3—C4	−10.7 (3)	C5—C6—C7—C8	−0.2 (3)
C2—N1—C3—C8	170.28 (17)	C6—C7—C8—C3	−0.3 (3)
C8—C3—C4—C5	−0.4 (3)	C4—C3—C8—C7	0.6 (3)
N1—C3—C4—C5	−179.38 (16)	N1—C3—C8—C7	179.72 (17)
C3—C4—C5—C6	−0.2 (3)	C6—O2—C9—C10	−173.33 (18)
C9—O2—C6—C5	−11.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1^i	0.86	2.14	2.898 (2)	147
C4—H4A···O1	0.93	2.36	2.945 (2)	120
C1—H1B···Cg1^ii	0.97	2.69	3.551	148
C9—H9B···Cg1^iii	0.97	2.77	3.650	152

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, −y, −z; (iii) −x+2, −y, −z.