3-Chloro-N-(4-meth-oxy-phen-yl)propanamide.

The title compound, C(10)H(12)ClNO(2), is a halogenated derivative of a secondary amide bearing an aromatic substituent. The C(=O)-N(H)-C(ar)-C(ar) torsion angle of -33.70 (18)° rules out the presence of resonance spanning the amide as well as the aromatic system. In the crystal, classical N-H⋯O hydrogen bonds, as well as C-H⋯O contacts connect the mol-ecules into chains propagating along the a axis.

Related literature

For structural similarity of N-substituted 2-aryl­acetamides to the lateral chain of natural benzyl­penicillin, see: Mijin & Marinkovic (2006 ▶); Mijin et al. (2008 ▶). For the coordination abilities of amides, see: Wu et al. (2008 ▶, 2010 ▶). For related structures, see: Akkurt et al. (2010 ▶); Huang & Xu, (2006 ▶); Moreno-Fuquen et al. (2011 ▶); Praveen et al. (2011 ▶). For the crystal structure of another compound featuring C—H⋯O contacts, see: Betz et al. (2011 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C10H12ClNO2

M = 213.66

Orthorhombic,

a = 9.6326 (3) Å

b = 8.6650 (2) Å

c = 25.7944 (8) Å

V = 2152.97 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.33 mm−1

T = 200 K

0.53 × 0.50 × 0.39 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.921, T max = 1.000

19180 measured reflections

2668 independent reflections

2401 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.096

S = 1.07

2668 reflections

132 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811040682/zj2028sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811040682/zj2028Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811040682/zj2028Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536811040682/zj2028Isup4.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H12ClNO2	Dx = 1.318 Mg m−3
Mr = 213.66	Melting point = 388–391 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9900 reflections
a = 9.6326 (3) Å	θ = 2.4–28.3°
b = 8.6650 (2) Å	µ = 0.33 mm−1
c = 25.7944 (8) Å	T = 200 K
V = 2152.97 (11) Å3	Block, violet
Z = 8	0.53 × 0.50 × 0.39 mm
F(000) = 896

Bruker APEXII CCD diffractometer	2668 independent reflections
Radiation source: fine-focus sealed tube	2401 reflections with I > 2σ(I)
graphite	Rint = 0.016
φ and ω scans	θmax = 28.3°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→12
Tmin = 0.921, Tmax = 1.000	k = −11→8
19180 measured reflections	l = −34→34

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0406P)2 + 0.8819P] where P = (Fo2 + 2Fc2)/3
2668 reflections	(Δ/σ)max = 0.001
132 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

	x	y	z	Uiso*/Ueq
Cl1	0.63232 (4)	0.05020 (5)	0.363132 (15)	0.05120 (13)
O1	0.45550 (9)	−0.07866 (13)	0.24620 (4)	0.0401 (2)
O2	0.60693 (14)	0.17364 (14)	0.01725 (4)	0.0571 (3)
N1	0.67622 (10)	−0.06661 (12)	0.21589 (4)	0.0278 (2)
H71	0.7614 (19)	−0.0778 (18)	0.2253 (6)	0.039 (4)*
C1	0.58029 (12)	−0.10651 (14)	0.25114 (5)	0.0277 (2)
C2	0.63650 (13)	−0.19487 (15)	0.29700 (5)	0.0333 (3)
H2A	0.6160	−0.3059	0.2922	0.040*
H2B	0.7387	−0.1828	0.2980	0.040*
C3	0.57679 (14)	−0.14268 (16)	0.34808 (5)	0.0359 (3)
H3A	0.6073	−0.2138	0.3759	0.043*
H3B	0.4742	−0.1460	0.3464	0.043*
C4	0.7094 (3)	0.2727 (3)	−0.00413 (8)	0.0945 (9)
H4A	0.7185	0.3650	0.0176	0.142*
H4B	0.6819	0.3030	−0.0393	0.142*
H4C	0.7986	0.2184	−0.0055	0.142*
C11	0.65289 (11)	0.00051 (13)	0.16640 (4)	0.0257 (2)
C12	0.53648 (12)	−0.03409 (14)	0.13633 (5)	0.0301 (2)
H12	0.4654	−0.0985	0.1498	0.036*
C13	0.52506 (13)	0.02579 (15)	0.08680 (5)	0.0344 (3)
H13	0.4458	0.0022	0.0664	0.041*
C14	0.62854 (15)	0.12028 (15)	0.06655 (5)	0.0367 (3)
C15	0.74430 (15)	0.15511 (16)	0.09623 (5)	0.0368 (3)
H15	0.8154	0.2194	0.0827	0.044*
C16	0.75527 (13)	0.09486 (15)	0.14610 (5)	0.0315 (3)
H16	0.8344	0.1189	0.1665	0.038*

	U11	U22	U33	U12	U13	U23
Cl1	0.0490 (2)	0.0532 (2)	0.0513 (2)	−0.01414 (17)	−0.00088 (16)	−0.01065 (16)
O1	0.0182 (4)	0.0644 (6)	0.0378 (5)	0.0037 (4)	0.0018 (3)	0.0059 (5)
O2	0.0822 (8)	0.0580 (7)	0.0312 (5)	−0.0186 (6)	−0.0137 (5)	0.0072 (5)
N1	0.0168 (4)	0.0368 (5)	0.0298 (5)	0.0016 (4)	−0.0016 (4)	0.0002 (4)
C1	0.0203 (5)	0.0319 (5)	0.0308 (5)	−0.0004 (4)	0.0000 (4)	−0.0018 (5)
C2	0.0274 (6)	0.0336 (6)	0.0389 (6)	0.0003 (5)	−0.0003 (5)	0.0068 (5)
C3	0.0330 (6)	0.0398 (7)	0.0350 (6)	−0.0080 (5)	0.0002 (5)	0.0094 (5)
C4	0.141 (2)	0.0964 (17)	0.0463 (10)	−0.0596 (17)	−0.0198 (12)	0.0292 (11)
C11	0.0219 (5)	0.0283 (5)	0.0268 (5)	0.0030 (4)	0.0009 (4)	−0.0046 (4)
C12	0.0240 (5)	0.0326 (6)	0.0337 (6)	−0.0012 (4)	−0.0024 (4)	−0.0044 (5)
C13	0.0331 (6)	0.0376 (6)	0.0324 (6)	0.0000 (5)	−0.0089 (5)	−0.0066 (5)
C14	0.0501 (8)	0.0333 (6)	0.0268 (5)	−0.0015 (6)	−0.0033 (5)	−0.0043 (5)
C15	0.0411 (7)	0.0376 (7)	0.0318 (6)	−0.0104 (6)	0.0034 (5)	−0.0030 (5)
C16	0.0266 (5)	0.0364 (6)	0.0315 (5)	−0.0051 (5)	−0.0003 (5)	−0.0058 (5)

Cl1—C3	1.7973 (14)	C4—H4A	0.9800
O1—C1	1.2326 (14)	C4—H4B	0.9800
O2—C14	1.3690 (16)	C4—H4C	0.9800
O2—C4	1.419 (2)	C11—C16	1.3838 (17)
N1—C1	1.3416 (15)	C11—C12	1.3961 (16)
N1—C11	1.4207 (15)	C12—C13	1.3832 (18)
N1—H71	0.861 (18)	C12—H12	0.9500
C1—C2	1.5096 (17)	C13—C14	1.3917 (19)
C2—C3	1.5070 (18)	C13—H13	0.9500
C2—H2A	0.9900	C14—C15	1.3858 (19)
C2—H2B	0.9900	C15—C16	1.3923 (18)
C3—H3A	0.9900	C15—H15	0.9500
C3—H3B	0.9900	C16—H16	0.9500
C14—O2—C4	117.35 (13)	O2—C4—H4C	109.5
C1—N1—C11	127.26 (10)	H4A—C4—H4C	109.5
C1—N1—H71	115.8 (11)	H4B—C4—H4C	109.5
C11—N1—H71	116.8 (11)	C16—C11—C12	119.28 (11)
O1—C1—N1	123.45 (11)	C16—C11—N1	117.98 (10)
O1—C1—C2	122.01 (11)	C12—C11—N1	122.57 (11)
N1—C1—C2	114.50 (10)	C13—C12—C11	119.76 (11)
C3—C2—C1	113.33 (10)	C13—C12—H12	120.1
C3—C2—H2A	108.9	C11—C12—H12	120.1
C1—C2—H2A	108.9	C12—C13—C14	120.69 (11)
C3—C2—H2B	108.9	C12—C13—H13	119.7
C1—C2—H2B	108.9	C14—C13—H13	119.7
H2A—C2—H2B	107.7	O2—C14—C15	124.19 (13)
C2—C3—Cl1	110.75 (9)	O2—C14—C13	116.00 (12)
C2—C3—H3A	109.5	C15—C14—C13	119.80 (12)
Cl1—C3—H3A	109.5	C14—C15—C16	119.33 (12)
C2—C3—H3B	109.5	C14—C15—H15	120.3
Cl1—C3—H3B	109.5	C16—C15—H15	120.3
H3A—C3—H3B	108.1	C11—C16—C15	121.13 (11)
O2—C4—H4A	109.5	C11—C16—H16	119.4
O2—C4—H4B	109.5	C15—C16—H16	119.4
H4A—C4—H4B	109.5
C11—N1—C1—O1	−5.5 (2)	C4—O2—C14—C15	−0.9 (2)
C11—N1—C1—C2	172.15 (11)	C4—O2—C14—C13	178.85 (18)
O1—C1—C2—C3	−45.01 (17)	C12—C13—C14—O2	−179.87 (12)
N1—C1—C2—C3	137.26 (11)	C12—C13—C14—C15	−0.1 (2)
C1—C2—C3—Cl1	−66.96 (12)	O2—C14—C15—C16	179.73 (13)
C1—N1—C11—C16	151.11 (12)	C13—C14—C15—C16	−0.1 (2)
C1—N1—C11—C12	−33.70 (18)	C12—C11—C16—C15	−0.27 (18)
C16—C11—C12—C13	0.14 (18)	N1—C11—C16—C15	175.08 (11)
N1—C11—C12—C13	−174.99 (11)	C14—C15—C16—C11	0.2 (2)
C11—C12—C13—C14	0.03 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H71···O1i	0.861 (18)	2.009 (18)	2.8643 (13)	172.1 (15)
C2—H2B···O1i	0.99	2.55	3.4203 (15)	147.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H71⋯O1i	0.861 (18)	2.009 (18)	2.8643 (13)	172.1 (15)
C2—H2B⋯O1i	0.99	2.55	3.4203 (15)	147

Symmetry code: (i) .