2-Chloro-N-(3,4-dimethyl­phen­yl)acetamide

Gowda, B.T.; Foro, S.; Terao, H.; Fuess, H.

doi:10.1107/S1600536809013051

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1022

doi:10.1107/S1600536809013051

Open

access

2-Chloro-N-(3,4-dimethylphenyl)acetamide

B. Thimme Gowda,^a ^* Sabine Foro,^b Hiromitsu Terao ^c and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany, and ^cFaculty of Integrated Arts and Sciences, Tokushima University, Minamijosanjima-cho, Tokushima 770-8502, Japan
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 1 April 2009; accepted 6 April 2009; online 10 April 2009)

The conformation of the C=O bond in the structure of the title compound, C₁₀H₁₂ClNO, is anti to the N—H bond and to the methylene H atoms in the side chain in both the independent molecules comprising the asymmetric unit. However, the conformation of the N—H bond is syn to the meta-methyl substituent in the aromatic ring of one of the molecules and anti in the other molecule. The two independent molecules are linked through intermolecular N—H⋯O hydrogen bonding into chains parallel to the b axis.

Related literature

For preparation of the compound, see: Shilpa & Gowda (2007 ). For related structures, see: Gowda et al. (2008a ,b ,c ).

Experimental

Crystal data

C₁₀H₁₂ClNO
M_r = 197.66
Triclinic, $[P \overline 1]$
a = 8.3672 (9) Å
b = 9.8076 (9) Å
c = 12.409 (1) Å
α = 95.415 (8)°
β = 96.492 (9)°
γ = 97.767 (9)°
V = 996.26 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 299 K
0.44 × 0.36 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany.]$ ) T_min = 0.868, T_max = 0.936
10754 measured reflections
3634 independent reflections
2874 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.127
S = 0.97
3634 reflections
240 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2	0.86	2.05	2.8992 (16)	172
N2—H2N⋯O1ⁱ	0.86	2.14	2.9802 (16)	166
Symmetry code: (i) x, y-1, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 $[Oxford Diffraction (2004). CrysAlis CCD. Oxford Diffraction Ltd, Köln, Germany.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809013051/dn2441sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809013051/dn2441Isup2.hkl

checkCIF report

Comment top

In the present work, as part of a study of the effect of ring and side chain substitutions on the crystal structures of aromatic amides (Gowda et al., 2008a,b,c), the structure of 2-chloro-N-(3,4-dimethylphenyl)acetamide (I) has been determined. The asymmetric unit of the structure contains two molecules (Fig. 1). The conformation of the N—H bond is syn to the meta-methyl substituent in the aromatic ring of one of the molecules and anti in the other molecule. The conformation of the C=O bond in the structure is anti to the N—H bond and to the side chain methylene H-atoms in the side chain (Fig. 1), in both the independent molecules comprising the asymmetric unit, similar to that observed in in 2-chloro-N- (2,4-dimethylphenyl)acetamide (Gowda et al., 2008a), in 2-chloro-N-(3,5-dichlorophenyl)acetamide (Gowda et al., 2008b), and in 2-chloro-N-(3-methylphenyl)acetamide (Gowda et al., 2008c). The two independent molecules in (I) are linked through intermolecular N—H···O hydrogen bonding (Fig.1) and the chains formed by H-bonding are parallel to the b axis (Table 1, Fig. 2).

Related literature top

For preparation of the compound, see: Shilpa & Gowda (2007). For background literature, see: Gowda et al. (2008a,b,c).

Experimental top

Compound (I) was prepared according to the literature method (Shilpa & Gowda, 2007). Single crystals were obtained from the slow evaporation of an ethanolic solution of (I).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I), showing the atom labeling scheme and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.

2-Chloro-N-(3,4-dimethylphenyl)acetamide top

Crystal data top

C₁₀H₁₂ClNO	Z = 4
M_r = 197.66	F(000) = 416
Triclinic, P1	D_x = 1.318 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3672 (9) Å	Cell parameters from 4345 reflections
b = 9.8076 (9) Å	θ = 2.8–27.6°
c = 12.409 (1) Å	µ = 0.34 mm⁻¹
α = 95.415 (8)°	T = 299 K
β = 96.492 (9)°	Rod, colourless
γ = 97.767 (9)°	0.44 × 0.36 × 0.20 mm
V = 996.26 (16) Å³

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3634 independent reflections
Radiation source: fine-focus sealed tube	2874 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
Rotation method data acquisition using ω and ϕ scans	θ_max = 25.4°, θ_min = 2.8°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −10→10
T_min = 0.868, T_max = 0.936	k = −11→11
10754 measured reflections	l = −14→14

Refinement top

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)] = 0.035	H-atom parameters constrained
wR(F²) = 0.127	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max < 0.001
3634 reflections	Δρ_max = 0.19 e Å⁻³
240 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.024 (4)

Crystal data top

C₁₀H₁₂ClNO	γ = 97.767 (9)°
M_r = 197.66	V = 996.26 (16) Å³
Triclinic, P1	Z = 4
a = 8.3672 (9) Å	Mo Kα radiation
b = 9.8076 (9) Å	µ = 0.34 mm⁻¹
c = 12.409 (1) Å	T = 299 K
α = 95.415 (8)°	0.44 × 0.36 × 0.20 mm
β = 96.492 (9)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	3634 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	2874 reflections with I > 2σ(I)
T_min = 0.868, T_max = 0.936	R_int = 0.017
10754 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 0.97	Δρ_max = 0.19 e Å⁻³
3634 reflections	Δρ_min = −0.23 e Å⁻³
240 parameters

Special details top

Experimental. Absorption correction: empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm, CrysAlis RED (Oxford Diffraction, 2007).

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

	x	y	z	U_iso*/U_eq
Cl1	0.62739 (6)	0.60024 (5)	0.62240 (4)	0.0701 (2)
O1	0.83974 (16)	0.76355 (11)	0.45971 (10)	0.0569 (3)
N1	0.81699 (17)	0.54085 (13)	0.38380 (11)	0.0477 (3)
H1N	0.8113	0.4570	0.3998	0.057*
C1	0.81633 (19)	0.55916 (15)	0.27115 (14)	0.0447 (4)
C2	0.9174 (2)	0.66380 (16)	0.23435 (14)	0.0482 (4)
H2	0.9875	0.7272	0.2846	0.058*
C3	0.9155 (2)	0.67553 (17)	0.12342 (14)	0.0490 (4)
C4	0.8120 (2)	0.57967 (18)	0.04769 (14)	0.0542 (4)
C5	0.7129 (2)	0.47505 (18)	0.08636 (16)	0.0627 (5)
H5	0.6434	0.4105	0.0367	0.075*
C6	0.7148 (2)	0.46423 (17)	0.19551 (16)	0.0575 (5)
H6	0.6474	0.3926	0.2190	0.069*
C7	0.82545 (19)	0.63949 (16)	0.46785 (14)	0.0446 (4)
C8	0.8184 (2)	0.58415 (19)	0.57750 (14)	0.0546 (4)
H8A	0.9049	0.6356	0.6304	0.066*
H8B	0.8339	0.4876	0.5710	0.066*
C9	1.0278 (3)	0.7913 (2)	0.08682 (19)	0.0753 (6)
H9A	1.0907	0.8458	0.1495	0.090*
H9B	0.9646	0.8488	0.0466	0.090*
H9C	1.0995	0.7528	0.0411	0.090*
C10	0.8062 (3)	0.5877 (3)	−0.07390 (16)	0.0781 (6)
H10A	0.9126	0.5838	−0.0949	0.094*
H10B	0.7710	0.6731	−0.0913	0.094*
H10C	0.7314	0.5112	−0.1126	0.094*
Cl2	0.90424 (8)	0.14166 (5)	0.21372 (4)	0.0779 (2)
O2	0.78329 (17)	0.24929 (11)	0.41405 (11)	0.0628 (4)
N2	0.74319 (15)	0.04521 (12)	0.48565 (10)	0.0414 (3)
H2N	0.7539	−0.0406	0.4734	0.050*
C11	0.67313 (18)	0.08227 (14)	0.58097 (12)	0.0379 (3)
C12	0.66625 (19)	−0.01217 (15)	0.65716 (12)	0.0428 (4)
H12	0.7076	−0.0946	0.6435	0.051*
C13	0.5996 (2)	0.01258 (16)	0.75308 (13)	0.0458 (4)
C14	0.53726 (19)	0.13642 (16)	0.77369 (13)	0.0459 (4)
C15	0.5432 (2)	0.22884 (16)	0.69622 (14)	0.0503 (4)
H15	0.5011	0.3110	0.7092	0.060*
C16	0.60886 (19)	0.20418 (15)	0.60076 (14)	0.0466 (4)
H16	0.6102	0.2683	0.5501	0.056*
C17	0.79504 (19)	0.12730 (15)	0.41182 (13)	0.0425 (4)
C18	0.8760 (2)	0.05019 (18)	0.32656 (13)	0.0519 (4)
H18A	0.8097	−0.0386	0.3018	0.062*
H18B	0.9808	0.0326	0.3598	0.062*
C19	0.5979 (3)	−0.0922 (2)	0.83395 (16)	0.0698 (6)
H19A	0.6609	−0.0513	0.9016	0.084*
H19B	0.6439	−0.1707	0.8058	0.084*
H19C	0.4879	−0.1216	0.8462	0.084*
C20	0.4663 (2)	0.1688 (2)	0.87824 (15)	0.0639 (5)
H20A	0.5468	0.1673	0.9396	0.077*
H20B	0.3736	0.1008	0.8819	0.077*
H20C	0.4333	0.2589	0.8797	0.077*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0802 (4)	0.0660 (3)	0.0721 (3)	0.0167 (3)	0.0302 (3)	0.0161 (2)
O1	0.0811 (9)	0.0320 (6)	0.0606 (7)	0.0144 (5)	0.0136 (6)	0.0069 (5)
N1	0.0598 (9)	0.0290 (6)	0.0568 (8)	0.0085 (6)	0.0128 (7)	0.0085 (6)
C1	0.0469 (9)	0.0323 (7)	0.0568 (9)	0.0115 (7)	0.0090 (7)	0.0041 (7)
C2	0.0470 (9)	0.0380 (8)	0.0578 (10)	0.0046 (7)	0.0043 (8)	0.0017 (7)
C3	0.0500 (10)	0.0447 (9)	0.0559 (10)	0.0142 (7)	0.0101 (8)	0.0097 (7)
C4	0.0570 (10)	0.0513 (10)	0.0570 (10)	0.0243 (8)	0.0029 (8)	0.0020 (8)
C5	0.0653 (12)	0.0478 (10)	0.0682 (12)	0.0054 (9)	−0.0037 (10)	−0.0101 (8)
C6	0.0618 (11)	0.0374 (8)	0.0703 (12)	0.0011 (8)	0.0095 (9)	−0.0023 (8)
C7	0.0437 (9)	0.0356 (8)	0.0567 (9)	0.0099 (7)	0.0073 (7)	0.0093 (7)
C8	0.0596 (11)	0.0477 (9)	0.0584 (10)	0.0104 (8)	0.0066 (8)	0.0126 (8)
C9	0.0797 (14)	0.0735 (14)	0.0735 (13)	−0.0002 (11)	0.0189 (11)	0.0176 (11)
C10	0.0970 (17)	0.0832 (15)	0.0568 (12)	0.0346 (13)	−0.0021 (11)	0.0040 (10)
Cl2	0.1111 (5)	0.0687 (3)	0.0604 (3)	0.0094 (3)	0.0316 (3)	0.0223 (2)
O2	0.0880 (10)	0.0318 (6)	0.0763 (8)	0.0136 (6)	0.0275 (7)	0.0190 (6)
N2	0.0518 (8)	0.0259 (6)	0.0483 (7)	0.0061 (5)	0.0106 (6)	0.0073 (5)
C11	0.0379 (8)	0.0299 (7)	0.0447 (8)	0.0025 (6)	0.0036 (6)	0.0037 (6)
C12	0.0499 (9)	0.0299 (7)	0.0508 (9)	0.0097 (6)	0.0084 (7)	0.0073 (6)
C13	0.0516 (9)	0.0404 (8)	0.0446 (8)	0.0056 (7)	0.0048 (7)	0.0046 (7)
C14	0.0440 (9)	0.0428 (8)	0.0485 (9)	0.0040 (7)	0.0046 (7)	−0.0027 (7)
C15	0.0528 (10)	0.0358 (8)	0.0636 (10)	0.0134 (7)	0.0093 (8)	0.0003 (7)
C16	0.0519 (9)	0.0322 (7)	0.0581 (10)	0.0102 (7)	0.0080 (8)	0.0101 (7)
C17	0.0458 (9)	0.0334 (8)	0.0480 (9)	0.0021 (6)	0.0059 (7)	0.0091 (6)
C18	0.0618 (11)	0.0465 (9)	0.0510 (9)	0.0088 (8)	0.0151 (8)	0.0134 (7)
C19	0.0980 (16)	0.0619 (11)	0.0592 (11)	0.0223 (11)	0.0262 (11)	0.0215 (9)
C20	0.0684 (12)	0.0652 (12)	0.0567 (11)	0.0089 (10)	0.0157 (9)	−0.0078 (9)

Geometric parameters (Å, º) top

Cl1—C8	1.7731 (19)	Cl2—C18	1.7539 (16)
O1—C7	1.2213 (18)	O2—C17	1.2117 (18)
N1—C7	1.343 (2)	N2—C17	1.3454 (19)
N1—C1	1.426 (2)	N2—C11	1.4171 (19)
N1—H1N	0.8600	N2—H2N	0.8600
C1—C6	1.382 (2)	C11—C12	1.385 (2)
C1—C2	1.385 (2)	C11—C16	1.388 (2)
C2—C3	1.391 (2)	C12—C13	1.385 (2)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.395 (2)	C13—C14	1.398 (2)
C3—C9	1.511 (3)	C13—C19	1.503 (2)
C4—C5	1.387 (3)	C14—C15	1.383 (2)
C4—C10	1.514 (3)	C14—C20	1.511 (2)
C5—C6	1.367 (3)	C15—C16	1.376 (2)
C5—H5	0.9300	C15—H15	0.9300
C6—H6	0.9300	C16—H16	0.9300
C7—C8	1.516 (2)	C17—C18	1.517 (2)
C8—H8A	0.9700	C18—H18A	0.9700
C8—H8B	0.9700	C18—H18B	0.9700
C9—H9A	0.9600	C19—H19A	0.9600
C9—H9B	0.9600	C19—H19B	0.9600
C9—H9C	0.9600	C19—H19C	0.9600
C10—H10A	0.9600	C20—H20A	0.9600
C10—H10B	0.9600	C20—H20B	0.9600
C10—H10C	0.9600	C20—H20C	0.9600

C7—N1—C1	127.45 (13)	C17—N2—C11	128.24 (12)
C7—N1—H1N	116.3	C17—N2—H2N	115.9
C1—N1—H1N	116.3	C11—N2—H2N	115.9
C6—C1—C2	118.88 (16)	C12—C11—C16	118.87 (14)
C6—C1—N1	118.09 (15)	C12—C11—N2	116.84 (13)
C2—C1—N1	122.98 (14)	C16—C11—N2	124.27 (13)
C1—C2—C3	120.99 (15)	C11—C12—C13	121.92 (14)
C1—C2—H2	119.5	C11—C12—H12	119.0
C3—C2—H2	119.5	C13—C12—H12	119.0
C2—C3—C4	119.72 (16)	C12—C13—C14	119.13 (15)
C2—C3—C9	119.26 (16)	C12—C13—C19	119.77 (15)
C4—C3—C9	121.02 (17)	C14—C13—C19	121.09 (16)
C5—C4—C3	118.29 (16)	C15—C14—C13	118.25 (15)
C5—C4—C10	120.04 (17)	C15—C14—C20	120.87 (16)
C3—C4—C10	121.68 (18)	C13—C14—C20	120.88 (16)
C6—C5—C4	121.78 (16)	C16—C15—C14	122.68 (15)
C6—C5—H5	119.1	C16—C15—H15	118.7
C4—C5—H5	119.1	C14—C15—H15	118.7
C5—C6—C1	120.34 (17)	C15—C16—C11	119.14 (14)
C5—C6—H6	119.8	C15—C16—H16	120.4
C1—C6—H6	119.8	C11—C16—H16	120.4
O1—C7—N1	124.51 (15)	O2—C17—N2	124.59 (15)
O1—C7—C8	121.48 (15)	O2—C17—C18	123.45 (14)
N1—C7—C8	114.00 (14)	N2—C17—C18	111.93 (13)
C7—C8—Cl1	109.74 (12)	C17—C18—Cl2	112.79 (12)
C7—C8—H8A	109.7	C17—C18—H18A	109.0
Cl1—C8—H8A	109.7	Cl2—C18—H18A	109.0
C7—C8—H8B	109.7	C17—C18—H18B	109.0
Cl1—C8—H8B	109.7	Cl2—C18—H18B	109.0
H8A—C8—H8B	108.2	H18A—C18—H18B	107.8
C3—C9—H9A	109.5	C13—C19—H19A	109.5
C3—C9—H9B	109.5	C13—C19—H19B	109.5
H9A—C9—H9B	109.5	H19A—C19—H19B	109.5
C3—C9—H9C	109.5	C13—C19—H19C	109.5
H9A—C9—H9C	109.5	H19A—C19—H19C	109.5
H9B—C9—H9C	109.5	H19B—C19—H19C	109.5
C4—C10—H10A	109.5	C14—C20—H20A	109.5
C4—C10—H10B	109.5	C14—C20—H20B	109.5
H10A—C10—H10B	109.5	H20A—C20—H20B	109.5
C4—C10—H10C	109.5	C14—C20—H20C	109.5
H10A—C10—H10C	109.5	H20A—C20—H20C	109.5
H10B—C10—H10C	109.5	H20B—C20—H20C	109.5

C7—N1—C1—C6	−140.52 (16)	C17—N2—C11—C12	−164.70 (14)
C7—N1—C1—C2	42.3 (2)	C17—N2—C11—C16	16.8 (2)
C6—C1—C2—C3	1.1 (2)	C16—C11—C12—C13	−1.1 (2)
N1—C1—C2—C3	178.30 (14)	N2—C11—C12—C13	−179.64 (14)
C1—C2—C3—C4	−0.8 (2)	C11—C12—C13—C14	0.1 (2)
C1—C2—C3—C9	180.00 (16)	C11—C12—C13—C19	−178.89 (16)
C2—C3—C4—C5	0.2 (2)	C12—C13—C14—C15	0.7 (2)
C9—C3—C4—C5	179.41 (17)	C19—C13—C14—C15	179.67 (16)
C2—C3—C4—C10	−179.69 (17)	C12—C13—C14—C20	−178.87 (15)
C9—C3—C4—C10	−0.5 (3)	C19—C13—C14—C20	0.1 (3)
C3—C4—C5—C6	0.0 (3)	C13—C14—C15—C16	−0.5 (3)
C10—C4—C5—C6	179.91 (18)	C20—C14—C15—C16	179.05 (16)
C4—C5—C6—C1	0.4 (3)	C14—C15—C16—C11	−0.5 (3)
C2—C1—C6—C5	−0.9 (3)	C12—C11—C16—C15	1.2 (2)
N1—C1—C6—C5	−178.21 (16)	N2—C11—C16—C15	179.71 (14)
C1—N1—C7—O1	−2.7 (3)	C11—N2—C17—O2	−3.0 (3)
C1—N1—C7—C8	178.29 (15)	C11—N2—C17—C18	175.03 (14)
O1—C7—C8—Cl1	73.33 (19)	O2—C17—C18—Cl2	−15.1 (2)
N1—C7—C8—Cl1	−107.59 (15)	N2—C17—C18—Cl2	166.82 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2	0.86	2.05	2.8992 (16)	172
N2—H2N···O1ⁱ	0.86	2.14	2.9802 (16)	166

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₂ClNO
M_r	197.66
Crystal system, space group	Triclinic, P1
Temperature (K)	299
a, b, c (Å)	8.3672 (9), 9.8076 (9), 12.409 (1)
α, β, γ (°)	95.415 (8), 96.492 (9), 97.767 (9)
V (Å³)	996.26 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.44 × 0.36 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.868, 0.936
No. of measured, independent and observed [I > 2σ(I)] reflections	10754, 3634, 2874
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.127, 0.97
No. of reflections	3634
No. of parameters	240
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.23

Computer programs: CrysAlis CCD (Oxford Diffraction, 2004), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2	0.86	2.05	2.8992 (16)	171.5
N2—H2N···O1ⁱ	0.86	2.14	2.9802 (16)	166.2

Symmetry code: (i) x, y−1, z.

References

Gowda, B. T., Foro, S. & Fuess, H. (2008a). Acta Cryst. E64, o85. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S. & Fuess, H. (2008b). Acta Cryst. E64, o420. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Svoboda, I., Foro, S., Dou, S. & Fuess, H. (2008c). Acta Cryst. E64, o208. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2004). CrysAlis CCD. Oxford Diffraction Ltd, Köln, Germany. Google Scholar
Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shilpa & Gowda, B. T. (2007). Z. Naturforsch. Teil A, 62, 84–90. Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1022

doi:10.1107/S1600536809013051

Open

access