2-Chloro-N-(3-methyl-phen-yl)acetamide.

The conformation of the N-H bond in the structure of the title compound, C(9)H(10)ClNO, is syn to the meta-methyl group, in contrast to the anti conformation observed with respect to the meta-nitro group in 2-chloro-N-(3-nitro-phen-yl)-acetamide. The asymmetric unit of the title compound contains two mol-ecules. The geometric parameters of the title compound are similar to those of 2-chloro-N-(4-methyl-phen-yl)-acetamide, 2-chloro-N-(3-nitro-phen-yl)acetamide and other acetanilides. Dual inter-molecular N-H⋯O hydrogen bonds link the mol-ecules in the direction of the a axis.

Related literature

For related literature, see: Gowda et al. (2006 ▶, 2007a ▶,b ▶,c ▶).

Experimental

Crystal data

C9H10ClNO

M = 183.63

Triclinic,

a = 8.326 (3) Å

b = 9.742 (3) Å

c = 11.491 (4) Å

α = 91.21 (1)°

β = 97.97 (1)°

γ = 98.08 (1)°

V = 913.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 299 (2) K

0.75 × 0.45 × 0.17 mm

Data collection

Stoe STADI-4 four-circle diffractometer

Absorption correction: ψ-scan (North et al., 1968 ▶) T min = 0.704, T max = 0.918

3214 measured reflections

3214 independent reflections

2651 reflections with I > 2σ(I)

3 standard reflections frequency: 180 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.136

S = 1.05

3214 reflections

221 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.33 e Å−3

Data collection: STADI4 (Stoe & Cie, 1987 ▶); cell refinement: STADI4; data reduction: REDU4 (Stoe & Cie, 1987 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807064847/dn2289sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064847/dn2289Isup2.hkl

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

C9H10ClNO	Z = 4
Mr = 183.63	F000 = 384
Triclinic, P1	Dx = 1.336 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.326 (3) Å	Cell parameters from 88 reflections
b = 9.742 (3) Å	θ = 18.0–22.6º
c = 11.491 (4) Å	µ = 0.37 mm−1
α = 91.21 (1)º	T = 299 (2) K
β = 97.97 (1)º	Flat prism, colourless
γ = 98.08 (1)º	0.75 × 0.45 × 0.17 mm
V = 913.1 (5) Å3

Stoe STADI-4 four-circle diffractometer	Rint = 0.0000
Radiation source: fine-focus sealed tube	θmax = 25.0º
Monochromator: graphite	θmin = 1.8º
T = 299(2) K	h = −9→9
Profile fitted scans 2θ/ω=1/1	k = −11→11
Absorption correction: empirical (using intensity measurements)(North et al., 1968)	l = 0→13
Tmin = 0.704, Tmax = 0.918	3 standard reflections
3214 measured reflections	every 180 min
3214 independent reflections	intensity decay: none
2651 reflections with I > 2σ(I)

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-atom parameters constrained
wR(F2) = 0.136	w = 1/[σ2(Fo2) + (0.0776P)2 + 0.2235P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3214 reflections	Δρmax = 0.37 e Å−3
221 parameters	Δρmin = −0.33 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.38090 (9)	0.90157 (7)	0.35203 (6)	0.0807 (3)
C1	0.1956 (3)	0.9307 (2)	0.40069 (18)	0.0552 (5)
H1A	0.1966	1.0295	0.4143	0.066*
H1B	0.1039	0.8970	0.3406	0.066*
C2	0.1756 (2)	0.85664 (19)	0.51299 (17)	0.0451 (4)
O1	0.16114 (19)	0.72994 (13)	0.51555 (13)	0.0570 (4)
N1	0.1734 (2)	0.94148 (15)	0.60666 (14)	0.0464 (4)
H1	0.1852	1.0290	0.5951	0.056*
C3	0.1537 (2)	0.90157 (18)	0.72263 (17)	0.0444 (4)
C4	0.2336 (2)	0.9904 (2)	0.81524 (18)	0.0518 (5)
H4	0.3003	1.0708	0.7996	0.062*
C5	0.2157 (3)	0.9613 (2)	0.93068 (19)	0.0606 (6)
C6	0.3022 (4)	1.0612 (4)	1.0296 (2)	0.0896 (9)
H6A	0.2223	1.0971	1.0698	0.108*	0.56 (3)
H6B	0.3678	1.1364	0.9980	0.108*	0.56 (3)
H6C	0.3712	1.0136	1.0838	0.108*	0.56 (3)
H6D	0.4186	1.0676	1.0313	0.108*	0.44 (3)
H6E	0.2730	1.0283	1.1031	0.108*	0.44 (3)
H6F	0.2697	1.1511	1.0173	0.108*	0.44 (3)
C7	0.1180 (3)	0.8405 (3)	0.9516 (2)	0.0731 (7)
H7	0.1062	0.8182	1.0286	0.088*
C8	0.0373 (3)	0.7520 (3)	0.8598 (2)	0.0752 (7)
H8	−0.0283	0.6711	0.8757	0.090*
C9	0.0528 (3)	0.7821 (2)	0.7446 (2)	0.0561 (5)
H9	−0.0034	0.7233	0.6830	0.067*
Cl2	0.11737 (11)	0.34078 (8)	0.80955 (6)	0.0934 (3)
C10	0.1373 (3)	0.4359 (2)	0.68356 (19)	0.0552 (5)
H10A	0.0296	0.4534	0.6483	0.066*
H10B	0.2035	0.5250	0.7063	0.066*
C11	0.2149 (2)	0.36313 (18)	0.59258 (17)	0.0458 (4)
O2	0.2274 (2)	0.24012 (14)	0.59346 (14)	0.0646 (4)
N2	0.26143 (19)	0.44939 (15)	0.51024 (14)	0.0449 (4)
H2	0.2476	0.5344	0.5204	0.054*
C12	0.3306 (2)	0.41834 (18)	0.40855 (16)	0.0429 (4)
C13	0.3227 (2)	0.5128 (2)	0.31995 (18)	0.0508 (5)
H13	0.2722	0.5908	0.3293	0.061*
C14	0.3889 (3)	0.4929 (2)	0.21770 (19)	0.0608 (5)
C15	0.3778 (5)	0.5963 (4)	0.1217 (3)	0.0957 (10)
H15A	0.3317	0.5485	0.0482	0.115*	0.58 (4)
H15B	0.4855	0.6434	0.1157	0.115*	0.58 (4)
H15C	0.3093	0.6627	0.1404	0.115*	0.58 (4)
H15D	0.4193	0.6879	0.1547	0.115*	0.42 (4)
H15E	0.2655	0.5930	0.0871	0.115*	0.42 (4)
H15F	0.4417	0.5737	0.0625	0.115*	0.42 (4)
C16	0.4629 (3)	0.3749 (2)	0.2057 (2)	0.0634 (6)
H16	0.5066	0.3588	0.1373	0.076*
C17	0.4722 (3)	0.2827 (2)	0.2932 (2)	0.0591 (5)
H17	0.5233	0.2050	0.2838	0.071*
C18	0.4068 (2)	0.30246 (19)	0.39596 (18)	0.0500 (5)
H18	0.4141	0.2391	0.4552	0.060*

	U11	U22	U33	U12	U13	U23
Cl1	0.0941 (5)	0.0763 (4)	0.0856 (5)	0.0268 (4)	0.0434 (4)	0.0205 (3)
C1	0.0660 (13)	0.0471 (11)	0.0538 (11)	0.0150 (9)	0.0065 (9)	0.0008 (9)
C2	0.0457 (10)	0.0383 (10)	0.0517 (10)	0.0097 (7)	0.0048 (8)	−0.0024 (8)
O1	0.0761 (10)	0.0348 (7)	0.0624 (9)	0.0128 (6)	0.0136 (7)	−0.0034 (6)
N1	0.0570 (9)	0.0306 (7)	0.0522 (9)	0.0080 (6)	0.0092 (7)	−0.0004 (6)
C3	0.0441 (10)	0.0387 (9)	0.0525 (11)	0.0120 (7)	0.0090 (8)	0.0004 (8)
C4	0.0528 (11)	0.0478 (10)	0.0551 (11)	0.0082 (9)	0.0089 (9)	−0.0041 (8)
C5	0.0609 (13)	0.0713 (14)	0.0532 (12)	0.0228 (11)	0.0086 (10)	−0.0025 (10)
C6	0.096 (2)	0.113 (2)	0.0581 (15)	0.0220 (17)	0.0037 (13)	−0.0182 (14)
C7	0.0863 (17)	0.0806 (17)	0.0607 (14)	0.0240 (14)	0.0256 (12)	0.0161 (12)
C8	0.0840 (17)	0.0607 (14)	0.0870 (18)	0.0042 (12)	0.0381 (14)	0.0144 (13)
C9	0.0550 (12)	0.0471 (11)	0.0674 (13)	0.0047 (9)	0.0160 (10)	−0.0012 (9)
Cl2	0.1420 (7)	0.0821 (5)	0.0695 (4)	0.0262 (4)	0.0490 (4)	0.0212 (3)
C10	0.0652 (13)	0.0455 (10)	0.0574 (12)	0.0059 (9)	0.0200 (10)	0.0012 (9)
C11	0.0464 (10)	0.0351 (9)	0.0555 (11)	0.0026 (7)	0.0089 (8)	0.0005 (8)
O2	0.0894 (11)	0.0347 (7)	0.0764 (10)	0.0123 (7)	0.0312 (8)	0.0091 (7)
N2	0.0530 (9)	0.0295 (7)	0.0540 (9)	0.0056 (6)	0.0144 (7)	−0.0001 (6)
C12	0.0413 (9)	0.0352 (9)	0.0500 (10)	−0.0007 (7)	0.0060 (8)	−0.0043 (7)
C13	0.0554 (11)	0.0431 (10)	0.0564 (11)	0.0104 (8)	0.0129 (9)	0.0025 (8)
C14	0.0697 (14)	0.0610 (13)	0.0536 (12)	0.0078 (10)	0.0169 (10)	0.0029 (10)
C15	0.136 (3)	0.099 (2)	0.0668 (17)	0.039 (2)	0.0418 (17)	0.0267 (15)
C16	0.0687 (14)	0.0658 (14)	0.0577 (13)	0.0052 (11)	0.0221 (10)	−0.0109 (10)
C17	0.0582 (12)	0.0476 (11)	0.0742 (14)	0.0101 (9)	0.0182 (10)	−0.0102 (10)
C18	0.0505 (11)	0.0399 (10)	0.0598 (12)	0.0072 (8)	0.0089 (9)	−0.0013 (8)

Cl1—C1	1.769 (2)	Cl2—C10	1.750 (2)
C1—C2	1.510 (3)	C10—C11	1.516 (3)
C1—H1A	0.9700	C10—H10A	0.9700
C1—H1B	0.9700	C10—H10B	0.9700
C2—O1	1.225 (2)	C11—O2	1.218 (2)
C2—N1	1.347 (2)	C11—N2	1.340 (2)
N1—C3	1.421 (3)	N2—C12	1.417 (3)
N1—H1	0.8600	N2—H2	0.8600
C3—C9	1.386 (3)	C12—C18	1.385 (3)
C3—C4	1.389 (3)	C12—C13	1.388 (3)
C4—C5	1.386 (3)	C13—C14	1.387 (3)
C4—H4	0.9300	C13—H13	0.9300
C5—C7	1.379 (4)	C14—C16	1.391 (3)
C5—C6	1.512 (4)	C14—C15	1.512 (3)
C6—H6A	0.9600	C15—H15A	0.9600
C6—H6B	0.9600	C15—H15B	0.9600
C6—H6C	0.9600	C15—H15C	0.9600
C6—H6D	0.9600	C15—H15D	0.9600
C6—H6E	0.9600	C15—H15E	0.9600
C6—H6F	0.9600	C15—H15F	0.9600
C7—C8	1.382 (4)	C16—C17	1.364 (3)
C7—H7	0.9300	C16—H16	0.9300
C8—C9	1.381 (3)	C17—C18	1.388 (3)
C8—H8	0.9300	C17—H17	0.9300
C9—H9	0.9300	C18—H18	0.9300
C2—C1—Cl1	109.99 (14)	C11—C10—Cl2	113.26 (15)
C2—C1—H1A	109.7	C11—C10—H10A	108.9
Cl1—C1—H1A	109.7	Cl2—C10—H10A	108.9
C2—C1—H1B	109.7	C11—C10—H10B	108.9
Cl1—C1—H1B	109.7	Cl2—C10—H10B	108.9
H1A—C1—H1B	108.2	H10A—C10—H10B	107.7
O1—C2—N1	124.31 (18)	O2—C11—N2	124.93 (19)
O1—C2—C1	121.44 (17)	O2—C11—C10	123.32 (18)
N1—C2—C1	114.25 (16)	N2—C11—C10	111.70 (16)
C2—N1—C3	126.86 (15)	C11—N2—C12	128.26 (16)
C2—N1—H1	116.6	C11—N2—H2	115.9
C3—N1—H1	116.6	C12—N2—H2	115.9
C9—C3—C4	120.1 (2)	C18—C12—C13	119.93 (18)
C9—C3—N1	122.24 (18)	C18—C12—N2	123.38 (17)
C4—C3—N1	117.60 (17)	C13—C12—N2	116.68 (17)
C5—C4—C3	121.0 (2)	C14—C13—C12	121.09 (19)
C5—C4—H4	119.5	C14—C13—H13	119.5
C3—C4—H4	119.5	C12—C13—H13	119.5
C7—C5—C4	118.3 (2)	C13—C14—C16	118.2 (2)
C7—C5—C6	121.8 (2)	C13—C14—C15	120.3 (2)
C4—C5—C6	119.9 (2)	C16—C14—C15	121.4 (2)
C5—C6—H6A	109.5	C14—C15—H15A	109.5
C5—C6—H6B	109.5	C14—C15—H15B	109.5
H6A—C6—H6B	109.5	H15A—C15—H15B	109.5
C5—C6—H6C	109.5	C14—C15—H15C	109.5
H6A—C6—H6C	109.5	H15A—C15—H15C	109.5
H6B—C6—H6C	109.5	H15B—C15—H15C	109.5
C5—C6—H6D	109.5	C14—C15—H15D	109.5
H6A—C6—H6D	141.1	H15A—C15—H15D	141.1
H6B—C6—H6D	56.3	H15B—C15—H15D	56.3
H6C—C6—H6D	56.3	H15C—C15—H15D	56.3
C5—C6—H6E	109.5	C14—C15—H15E	109.5
H6A—C6—H6E	56.3	H15A—C15—H15E	56.3
H6B—C6—H6E	141.1	H15B—C15—H15E	141.1
H6C—C6—H6E	56.3	H15C—C15—H15E	56.3
H6D—C6—H6E	109.5	H15D—C15—H15E	109.5
C5—C6—H6F	109.5	C14—C15—H15F	109.5
H6A—C6—H6F	56.3	H15A—C15—H15F	56.3
H6B—C6—H6F	56.3	H15B—C15—H15F	56.3
H6C—C6—H6F	141.1	H15C—C15—H15F	141.1
H6D—C6—H6F	109.5	H15D—C15—H15F	109.5
H6E—C6—H6F	109.5	H15E—C15—H15F	109.5
C5—C7—C8	120.9 (2)	C17—C16—C14	120.7 (2)
C5—C7—H7	119.6	C17—C16—H16	119.6
C8—C7—H7	119.6	C14—C16—H16	119.6
C9—C8—C7	120.8 (2)	C16—C17—C18	121.3 (2)
C9—C8—H8	119.6	C16—C17—H17	119.4
C7—C8—H8	119.6	C18—C17—H17	119.4
C8—C9—C3	118.8 (2)	C12—C18—C17	118.73 (19)
C8—C9—H9	120.6	C12—C18—H18	120.6
C3—C9—H9	120.6	C17—C18—H18	120.6
Cl1—C1—C2—O1	−63.8 (2)	Cl2—C10—C11—O2	16.0 (3)
Cl1—C1—C2—N1	116.98 (16)	Cl2—C10—C11—N2	−166.24 (14)
O1—C2—N1—C3	−0.3 (3)	O2—C11—N2—C12	1.1 (3)
C1—C2—N1—C3	178.88 (17)	C10—C11—N2—C12	−176.62 (18)
C2—N1—C3—C9	−35.4 (3)	C11—N2—C12—C18	−20.4 (3)
C2—N1—C3—C4	147.54 (19)	C11—N2—C12—C13	161.13 (18)
C9—C3—C4—C5	0.6 (3)	C18—C12—C13—C14	0.6 (3)
N1—C3—C4—C5	177.68 (18)	N2—C12—C13—C14	179.07 (18)
C3—C4—C5—C7	0.9 (3)	C12—C13—C14—C16	0.4 (3)
C3—C4—C5—C6	−179.0 (2)	C12—C13—C14—C15	179.5 (2)
C4—C5—C7—C8	−1.2 (4)	C13—C14—C16—C17	−1.0 (4)
C6—C5—C7—C8	178.6 (2)	C15—C14—C16—C17	179.9 (3)
C5—C7—C8—C9	0.2 (4)	C14—C16—C17—C18	0.7 (4)
C7—C8—C9—C3	1.3 (4)	C13—C12—C18—C17	−0.9 (3)
C4—C3—C9—C8	−1.7 (3)	N2—C12—C18—C17	−179.25 (17)
N1—C3—C9—C8	−178.6 (2)	C16—C17—C18—C12	0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	2.04	2.891 (2)	171
N2—H2···O1	0.86	2.13	2.970 (2)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	2.04	2.891 (2)	171
N2—H2⋯O1	0.86	2.13	2.970 (2)	166

Symmetry code: (i) .