4-Chloro-N-methyl-benzamide.

There are two mol-ecules in the asymmetric unit of the title compound, C(8)H(8)ClNO, which are linked in the crystal structure via N-H⋯O hydrogen bonds into chains along the b axis. C-H⋯O contacts also occur. The benzene ring makes dihedral angles of 5.9 (1) and 16.7 (1)°with the attached amide group in the two independent molecules.

Related literature

For applications of the title compound and background to the synthesis, see: Lee et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C8H8ClNO

M = 169.61

Triclinic,

a = 3.9420 (8) Å

b = 9.2250 (18) Å

c = 21.864 (4) Å

α = 96.46 (3)°

β = 90.34 (3)°

γ = 90.99 (3)°

V = 789.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.42 mm−1

T = 296 K

0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.921, T max = 0.959

3079 measured reflections

2887 independent reflections

1633 reflections with I > 2σ(I)

R int = 0.047

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.188

S = 1.00

2887 reflections

199 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812008641/bq2339sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008641/bq2339Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812008641/bq2339Isup3.cml

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

C8H8ClNO	Z = 4
Mr = 169.61	F(000) = 352
Triclinic, P1	Dx = 1.426 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 3.9420 (8) Å	Cell parameters from 25 reflections
b = 9.2250 (18) Å	θ = 9–12°
c = 21.864 (4) Å	µ = 0.42 mm−1
α = 96.46 (3)°	T = 296 K
β = 90.34 (3)°	Block, colourless
γ = 90.99 (3)°	0.20 × 0.10 × 0.10 mm
V = 789.9 (3) Å3

Enraf–Nonius CAD-4 diffractometer	1633 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.047
Graphite monochromator	θmax = 25.4°, θmin = 1.9°
ω/2θ scans	h = −4→4
Absorption correction: ψ scan (North et al., 1968)	k = −11→0
Tmin = 0.921, Tmax = 0.959	l = −26→26
3079 measured reflections	3 standard reflections every 200 reflections
2887 independent reflections	intensity decay: 1%

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.188	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.094P)2] where P = (Fo2 + 2Fc2)/3
2887 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.29 e Å−3
2 restraints	Δρmin = −0.25 e Å−3

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
Cl1	1.2503 (4)	0.71959 (16)	1.02286 (5)	0.0971 (5)
N1	0.7112 (8)	0.7694 (3)	0.73236 (14)	0.0536 (8)
H1A	0.6619	0.6842	0.7424	0.064*
O1	0.9592 (8)	0.9833 (3)	0.75794 (13)	0.0748 (9)
C1	1.1009 (11)	0.9251 (5)	0.87664 (19)	0.0723 (13)
H1B	1.1381	1.0195	0.8667	0.087*
C2	1.1874 (12)	0.8941 (5)	0.9344 (2)	0.0751 (13)
H2A	1.2858	0.9658	0.9626	0.090*
C3	1.1290 (11)	0.7593 (5)	0.94995 (19)	0.0642 (11)
C4	0.9934 (12)	0.6541 (5)	0.9090 (2)	0.0732 (13)
H4A	0.9623	0.5610	0.9207	0.088*
C5	0.8993 (12)	0.6791 (4)	0.85058 (19)	0.0659 (12)
H5A	0.7988	0.6064	0.8231	0.079*
C6	0.9649 (9)	0.8253 (3)	0.83385 (16)	0.0478 (9)
C7	0.8729 (9)	0.8632 (4)	0.77223 (17)	0.0470 (9)
C8	0.6136 (11)	0.8043 (4)	0.67242 (18)	0.0625 (11)
H8A	0.4946	0.7224	0.6507	0.094*
H8B	0.8125	0.8266	0.6499	0.094*
H8C	0.4683	0.8872	0.6766	0.094*
Cl2	0.3429 (3)	0.77031 (14)	0.52328 (5)	0.0843 (5)
O2	−0.3948 (7)	0.5109 (3)	0.25934 (13)	0.0690 (8)
N2	−0.3020 (8)	0.7363 (3)	0.23575 (14)	0.0575 (9)
H2B	−0.2129	0.8209	0.2470	0.069*
C9	−0.0638 (11)	0.8149 (4)	0.36052 (18)	0.0615 (11)
H9A	−0.1235	0.8915	0.3386	0.074*
C10	0.0805 (11)	0.8473 (4)	0.41801 (18)	0.0626 (11)
H10A	0.1145	0.9435	0.4350	0.075*
C11	0.1731 (10)	0.7327 (4)	0.44960 (18)	0.0592 (10)
C12	0.1202 (10)	0.5922 (4)	0.42494 (18)	0.0608 (11)
H12A	0.1841	0.5163	0.4470	0.073*
C13	−0.0237 (10)	0.5619 (4)	0.36903 (18)	0.0593 (11)
H13A	−0.0589	0.4652	0.3528	0.071*
C14	−0.1232 (9)	0.6758 (3)	0.33430 (16)	0.0444 (8)
C15	−0.2870 (10)	0.6352 (4)	0.27428 (17)	0.0504 (9)
C16	−0.4602 (11)	0.7105 (4)	0.17627 (19)	0.0694 (12)
H16A	−0.4403	0.7968	0.1557	0.104*
H16B	−0.6957	0.6861	0.1809	0.104*
H16C	−0.3507	0.6312	0.1524	0.104*

	U11	U22	U33	U12	U13	U23
Cl1	0.1301 (12)	0.1145 (11)	0.0491 (7)	−0.0039 (8)	−0.0234 (7)	0.0221 (7)
N1	0.076 (2)	0.0421 (17)	0.0432 (18)	−0.0096 (15)	−0.0155 (15)	0.0103 (14)
O1	0.113 (2)	0.0438 (16)	0.069 (2)	−0.0172 (15)	−0.0122 (17)	0.0171 (14)
C1	0.102 (3)	0.062 (3)	0.053 (3)	−0.020 (2)	−0.011 (2)	0.012 (2)
C2	0.099 (3)	0.072 (3)	0.052 (3)	−0.032 (2)	−0.022 (2)	0.001 (2)
C3	0.072 (3)	0.072 (3)	0.051 (3)	0.015 (2)	−0.002 (2)	0.013 (2)
C4	0.116 (4)	0.052 (2)	0.053 (3)	−0.005 (2)	−0.010 (2)	0.015 (2)
C5	0.104 (3)	0.041 (2)	0.054 (3)	−0.004 (2)	−0.013 (2)	0.0096 (17)
C6	0.061 (2)	0.0419 (19)	0.039 (2)	−0.0028 (16)	−0.0064 (17)	0.0023 (15)
C7	0.058 (2)	0.0308 (18)	0.054 (2)	0.0032 (16)	−0.0016 (17)	0.0098 (15)
C8	0.080 (3)	0.061 (2)	0.048 (2)	0.005 (2)	−0.012 (2)	0.0118 (18)
Cl2	0.1028 (9)	0.1021 (10)	0.0483 (7)	0.0030 (7)	−0.0151 (6)	0.0110 (6)
O2	0.099 (2)	0.0387 (15)	0.068 (2)	−0.0151 (14)	−0.0110 (16)	0.0061 (13)
N2	0.085 (2)	0.0421 (17)	0.046 (2)	−0.0030 (15)	−0.0068 (16)	0.0078 (14)
C9	0.093 (3)	0.041 (2)	0.052 (3)	0.002 (2)	−0.015 (2)	0.0115 (17)
C10	0.102 (3)	0.037 (2)	0.049 (2)	0.001 (2)	−0.003 (2)	0.0020 (16)
C11	0.064 (3)	0.067 (3)	0.047 (2)	0.015 (2)	0.0010 (19)	0.0052 (19)
C12	0.079 (3)	0.053 (2)	0.054 (3)	0.011 (2)	−0.008 (2)	0.0194 (19)
C13	0.080 (3)	0.042 (2)	0.057 (3)	0.0145 (19)	0.003 (2)	0.0108 (18)
C14	0.052 (2)	0.0384 (19)	0.043 (2)	0.0040 (15)	0.0077 (16)	0.0034 (15)
C15	0.064 (2)	0.044 (2)	0.044 (2)	0.0031 (17)	0.0059 (18)	0.0069 (17)
C16	0.086 (3)	0.066 (3)	0.057 (3)	−0.007 (2)	−0.022 (2)	0.013 (2)

Cl1—C3	1.741 (4)	Cl2—C11	1.737 (4)
N1—C7	1.311 (4)	O2—C15	1.224 (4)
N1—C8	1.436 (4)	N2—C15	1.327 (4)
N1—H1A	0.8600	N2—C16	1.433 (5)
O1—C7	1.227 (4)	N2—H2B	0.8600
C1—C6	1.339 (5)	C9—C14	1.360 (5)
C1—C2	1.368 (6)	C9—C10	1.376 (5)
C1—H1B	0.9300	C9—H9A	0.9300
C2—C3	1.342 (6)	C10—C11	1.379 (5)
C2—H2A	0.9300	C10—H10A	0.9300
C3—C4	1.345 (6)	C11—C12	1.359 (5)
C4—C5	1.373 (5)	C12—C13	1.343 (5)
C4—H4A	0.9300	C12—H12A	0.9300
C5—C6	1.456 (4)	C13—C14	1.423 (5)
C5—H5A	0.9300	C13—H13A	0.9300
C6—C7	1.474 (5)	C14—C15	1.467 (5)
C8—H8A	0.9600	C16—H16A	0.9600
C8—H8B	0.9600	C16—H16B	0.9600
C8—H8C	0.9600	C16—H16C	0.9600
C7—N1—C8	122.2 (3)	C15—N2—C16	122.8 (3)
C7—N1—H1A	118.9	C15—N2—H2B	118.6
C8—N1—H1A	118.9	C16—N2—H2B	118.6
C6—C1—C2	122.7 (4)	C14—C9—C10	123.0 (3)
C6—C1—H1B	118.6	C14—C9—H9A	118.5
C2—C1—H1B	118.6	C10—C9—H9A	118.5
C3—C2—C1	119.4 (4)	C9—C10—C11	117.9 (4)
C3—C2—H2A	120.3	C9—C10—H10A	121.0
C1—C2—H2A	120.3	C11—C10—H10A	121.0
C2—C3—C4	120.7 (4)	C12—C11—C10	121.0 (4)
C2—C3—Cl1	119.0 (3)	C12—C11—Cl2	120.0 (3)
C4—C3—Cl1	120.2 (3)	C10—C11—Cl2	118.9 (3)
C3—C4—C5	122.5 (4)	C13—C12—C11	120.5 (4)
C3—C4—H4A	118.8	C13—C12—H12A	119.7
C5—C4—H4A	118.8	C11—C12—H12A	119.7
C4—C5—C6	116.6 (4)	C12—C13—C14	120.9 (4)
C4—C5—H5A	121.7	C12—C13—H13A	119.6
C6—C5—H5A	121.7	C14—C13—H13A	119.6
C1—C6—C5	118.1 (4)	C9—C14—C13	116.7 (4)
C1—C6—C7	121.1 (3)	C9—C14—C15	125.2 (3)
C5—C6—C7	120.8 (3)	C13—C14—C15	118.1 (3)
O1—C7—N1	120.1 (3)	O2—C15—N2	121.1 (4)
O1—C7—C6	118.8 (3)	O2—C15—C14	121.2 (3)
N1—C7—C6	121.1 (3)	N2—C15—C14	117.6 (3)
N1—C8—H8A	109.5	N2—C16—H16A	109.5
N1—C8—H8B	109.5	N2—C16—H16B	109.5
H8A—C8—H8B	109.5	H16A—C16—H16B	109.5
N1—C8—H8C	109.5	N2—C16—H16C	109.5
H8A—C8—H8C	109.5	H16A—C16—H16C	109.5
H8B—C8—H8C	109.5	H16B—C16—H16C	109.5
C6—C1—C2—C3	−1.4 (7)	C14—C9—C10—C11	1.1 (6)
C1—C2—C3—C4	1.4 (7)	C9—C10—C11—C12	−0.7 (6)
C1—C2—C3—Cl1	178.3 (4)	C9—C10—C11—Cl2	−177.9 (3)
C2—C3—C4—C5	−1.9 (7)	C10—C11—C12—C13	0.1 (6)
Cl1—C3—C4—C5	−178.8 (4)	Cl2—C11—C12—C13	177.3 (3)
C3—C4—C5—C6	2.2 (7)	C11—C12—C13—C14	0.2 (6)
C2—C1—C6—C5	1.7 (7)	C10—C9—C14—C13	−0.9 (6)
C2—C1—C6—C7	179.6 (4)	C10—C9—C14—C15	177.7 (4)
C4—C5—C6—C1	−2.0 (6)	C12—C13—C14—C9	0.2 (6)
C4—C5—C6—C7	−179.9 (4)	C12—C13—C14—C15	−178.4 (4)
C8—N1—C7—O1	−3.2 (6)	C16—N2—C15—O2	3.7 (6)
C8—N1—C7—C6	179.0 (3)	C16—N2—C15—C14	−179.0 (3)
C1—C6—C7—O1	8.5 (6)	C9—C14—C15—O2	−164.7 (4)
C5—C6—C7—O1	−173.6 (4)	C13—C14—C15—O2	13.9 (5)
C1—C6—C7—N1	−173.6 (4)	C9—C14—C15—N2	18.0 (6)
C5—C6—C7—N1	4.3 (5)	C13—C14—C15—N2	−163.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.86	2.07	2.876 (4)	157
N2—H2B···O1ii	0.86	2.06	2.887 (4)	160
C5—H5A···O2i	0.93	2.53	3.417 (5)	159
C9—H9A···O1ii	0.93	2.60	3.379 (5)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.86	2.07	2.876 (4)	157
N2—H2B⋯O1ii	0.86	2.06	2.887 (4)	160
C5—H5A⋯O2i	0.93	2.53	3.417 (5)	159
C9—H9A⋯O1ii	0.93	2.60	3.379 (5)	142

Symmetry codes: (i) ; (ii) .