2-Chloro-N-(3-methyl­phen­yl)acetamide

Gowda, B.T.; Svoboda, I.; Foro, S.; Dou, S.; Fuess, H.

doi:10.1107/S1600536807064847

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o208

https://doi.org/10.1107/S1600536807064847

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2-Chloro-N-(3-methylphenyl)acetamide

B. Thimme Gowda,^a ^* Ingrid Svoboda,^b Sabine Foro,^b Shi-qi Dou ^b and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 18 November 2007; accepted 30 November 2007; online 6 December 2007)

The conformation of the N—H bond in the structure of the title compound, C₉H₁₀ClNO, 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-nitrophenyl)acetamide. The asymmetric unit of the title compound contains two molecules. The geometric parameters of the title compound are similar to those of 2-chloro-N-(4-methylphenyl)acetamide, 2-chloro-N-(3-nitrophenyl)acetamide and other acetanilides. Dual intermolecular N—H⋯O hydrogen bonds link the molecules 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_r = 183.63
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.046
wR(F²) = 0.136
S = 1.05
3214 reflections
221 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.33 e Å⁻³

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) x, y+1, z.

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807064847/dn2289Isup2.hkl

checkCIF report

Comment top

In the present work, the structure of 2-chloro-N-(3-methylphenyl)- acetamide (3MPCA) has been determined as part of a study of the effect of ring and side chain substitutions on the solid state geometry of aromatic amides (Gowda et al., 2007a, 2007b, 2007c). The conformation of the N—H bond in the structure of 3MPCA is syn to the meta methyl group, in contrast to the anti conformation observed with respect to the meta nitro group in the 2-chloro-N-(3-nitrophenyl)acetamide (3NPCA)(Gowda et al., 2007b). The asymmetric unit of 3MPCA crystal contains two molecules. The geometric parameters of 3MPCA are similar to those of 3NPCA (Gowda et al., 2007b), 2-chloro-N-(4-methylphenyl)- acetamide (Gowda et al., 2007a), 2-chloro-N- (2-chlorophenyl)-acetamide (Gowda et al., 2007c) and other acetanilides. The molecules in 3MPcA are linked into infinite diagonal chains through dual intermolecular N1—H1···O2 and N2—H2—O1 hydrogen bonding in the bc plane (Table 1 and Fig.2).

Related literature top

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

Experimental top

The title compound was prepared according to the literature method (Gowda et al., 2006). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra (Gowda et al., 2006). Single crystals of the title compound were obtained from an ethanolic solution and used for X-ray diffraction studies at room temperature.

Structure description top

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

Computing details top

Data collection: STADI4 (Stoe & Cie, 1987); cell refinement: STADI4 (Stoe & Cie, 1987); 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 (Sheldrick, 1997).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii. H bond is shown as dashed line.
	Fig. 2. Partial packing view showing the formation of the chain through N—H···O hydrogen bondings. H atoms not involved in H bonds have been omitted for clarity. H bonds are shown as dashed lines. [Symmetry code: (i) x, y + 1, z]

2-Chloro-N-(3-methylphenyl)acetamide top

Crystal data top

C₉H₁₀ClNO	Z = 4
M_r = 183.63	F(000) = 384
Triclinic, P1	D_x = 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 = 18.0–22.6°
c = 11.491 (4) Å	µ = 0.37 mm⁻¹
α = 91.21 (1)°	T = 299 K
β = 97.97 (1)°	Flat prism, colourless
γ = 98.08 (1)°	0.75 × 0.45 × 0.17 mm
V = 913.1 (5) Å³

Data collection top

Stoe STADI-4 four-circle diffractometer	2651 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 25.0°, θ_min = 1.8°
Profile fitted scans 2θ/ω=1/1	h = −9→9
Absorption correction: empirical (using intensity measurements) (North et al., 1968)	k = −11→11
T_min = 0.704, T_max = 0.918	l = 0→13
3214 measured reflections	3 standard reflections every 180 min
3214 independent reflections	intensity decay: none

Refinement top

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0776P)² + 0.2235P] where P = (F_o² + 2F_c²)/3
3214 reflections	(Δ/σ)_max = 0.001
221 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₉H₁₀ClNO	γ = 98.08 (1)°
M_r = 183.63	V = 913.1 (5) Å³
Triclinic, P1	Z = 4
a = 8.326 (3) Å	Mo Kα radiation
b = 9.742 (3) Å	µ = 0.37 mm⁻¹
c = 11.491 (4) Å	T = 299 K
α = 91.21 (1)°	0.75 × 0.45 × 0.17 mm
β = 97.97 (1)°

Data collection top

Stoe STADI-4 four-circle diffractometer	2651 reflections with I > 2σ(I)
Absorption correction: empirical (using intensity measurements) (North et al., 1968)	R_int = 0.000
T_min = 0.704, T_max = 0.918	3 standard reflections every 180 min
3214 measured reflections	intensity decay: none
3214 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.05	Δρ_max = 0.37 e Å⁻³
3214 reflections	Δρ_min = −0.33 e Å⁻³
221 parameters

Special details top

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	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₉H₁₀ClNO
M_r	183.63
Crystal system, space group	Triclinic, P1
Temperature (K)	299
a, b, c (Å)	8.326 (3), 9.742 (3), 11.491 (4)
α, β, γ (°)	91.21 (1), 97.97 (1), 98.08 (1)
V (Å³)	913.1 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.75 × 0.45 × 0.17

Data collection
Diffractometer	Stoe STADI-4 four-circle diffractometer
Absorption correction	Empirical (using intensity measurements) (North et al., 1968)
T_min, T_max	0.704, 0.918
No. of measured, independent and observed [I > 2σ(I)] reflections	3214, 3214, 2651
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.136, 1.05
No. of reflections	3214
No. of parameters	221
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.33

Computer programs: STADI4 (Stoe & Cie, 1987), REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.86	2.04	2.891 (2)	171.4
N2—H2···O1	0.86	2.13	2.970 (2)	166.0

Symmetry code: (i) x, y+1, z.

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.

References

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