N-[2-(1,3-Benzodioxol-5-yl)eth­yl]-2-chloro­acetamide

Dong, H.-C.

doi:10.1107/S1600536808014232

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1118

doi:10.1107/S1600536808014232

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N-[2-(1,3-Benzodioxol-5-yl)ethyl]-2-chloroacetamide

Hui-Chao Dong ^a ^*

^aHenan Provincial Key Laboratory of Surface & Interface Science, Zhengzhou University of Light Industry, Zhengzhou 450002, People's Republic of China
^*Correspondence e-mail: donghuichao6503@yahoo.cn

(Received 6 May 2008; accepted 12 May 2008; online 21 May 2008)

The title compound, C₁₁H₁₂ClNO₃, crystallizes with two independent molecules in the asymmetric unit. Intermolecular N—H⋯O hydrogen bonds link the molecules related by translation along the b axis into two independent hydrogen-bonded chains. The crystal studied exhibited inversion twinning.

Related literature

For the crystal structures of related compounds, see: Kuehne et al. (1988 ). For details of the aplication of N-(2-benzo[1,3]dioxol-5-yl-ethyl)-2-chloro-acetamide, see: Bernhard & Snieckus (1971 ); Ma et al. (2006 ). For bond-length data, see Allen et al. (1987 ).

Experimental

Crystal data

C₁₁H₁₂ClNO₃
M_r = 241.67
Orthorhombic, P c a 2₁
a = 14.429 (3) Å
b = 5.1258 (10) Å
c = 30.679 (6) Å
V = 2269.1 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 293 (2) K
0.20 × 0.12 × 0.09 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.937, T_max = 0.971
15836 measured reflections
3949 independent reflections
2946 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.110
S = 1.13
3949 reflections
290 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.34 e Å⁻³
Absolute structure: Flack (1983 ), 1304 Friedel pairs
Flack parameter: 0.47 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3ⁱ	0.86	2.18	2.894 (4)	140
N2—H2B⋯O6ⁱⁱ	0.86	2.18	2.894 (4)	140
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z.

Data collection: RAPID-AUTO (Rigaku, 2004 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808014232/cv2412sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808014232/cv2412Isup2.hkl

checkCIF report

Comment top

The title compound (I) is an important intermediate for the synthesis of3, 4-dihydroisoquinoline and some other heterocyclic compounds (Bernhard & Snieckus, 1971; Ma et al., 2006). In this paper, we report its crystal structure.

Compound (I) crystallizes with two independent molecules in the non-centrosymmetric unit cell (Fig. 1). All bond lengths and angles in (I) are normal (Allen et al., 1987) and in a good agreement with those reported previously (Kuehne et al., 1988). The intermolecular N—H···O hydrogen bonds (Table 1) link the molecules related by translation along b axis into two independent hydrogen-bonded chains.

Related literature top

For the crystal structures of related compounds, see: Kuehne et al. (1988). For details of the aplication of N-(2-benzo[1,3]dioxol-5-yl-ethyl)-2-chloro-acetamide, see: Bernhard & Snieckus (1971); Ma et al. (2006). For bond-length data, see Allen et al. (1987).

Experimental top

2-Benzo[1,3]dioxol-5-yl-ethylamine (20 mmol) was dissolved in CH₂Cl₂, and K₂CO₃ (30 mmol) was added, then chloroacetyl chloride (20 mmol) was added during 30 min at 273 K. After 2 h standing at room temperature, the solution was washed with water, the organic layer was separated, dried with Na₂SO₄ and evaporated to obtain the primary product. The pure product was isolated by recrystallization from ethyl acetate (1.50 g, 68%). Single crystals suitable for X-ray measurements were obtained by recrystallization from ethyl acetate at room temperature.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO (Rigaku, 2004); data reduction: RAPID-AUTO (Rigaku, 2004); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The content of asymmetric unit of (I), with atomic labels and 40% probability displacement ellipsoids for non-H atoms.

N-[2-(1,3-Benzodioxol-5-yl)ethyl]-2-chloroacetamide top

Crystal data top

C₁₁H₁₂ClNO₃	F(000) = 1008
M_r = 241.67	D_x = 1.415 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2501 reflections
a = 14.429 (3) Å	θ = 2.3–25.1°
b = 5.1258 (10) Å	µ = 0.33 mm⁻¹
c = 30.679 (6) Å	T = 293 K
V = 2269.1 (8) Å³	Needle, colourless
Z = 8	0.20 × 0.12 × 0.09 mm

Data collection top

Rigaku R-AXIS RAPID IP area-detector diffractometer	3949 independent reflections
Radiation source: Rotating Anode	2946 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω oscillation scans	θ_max = 25.0°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −17→17
T_min = 0.937, T_max = 0.971	k = −5→6
15836 measured reflections	l = −36→36

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.035	w = 1/[σ²(F_o²) + (0.0541P)² + 0.2974P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.110	(Δ/σ)_max = 0.001
S = 1.13	Δρ_max = 0.34 e Å⁻³
3949 reflections	Δρ_min = −0.35 e Å⁻³
290 parameters	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0035 (6)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1304 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.47 (8)

Crystal data top

C₁₁H₁₂ClNO₃	V = 2269.1 (8) Å³
M_r = 241.67	Z = 8
Orthorhombic, Pca2₁	Mo Kα radiation
a = 14.429 (3) Å	µ = 0.33 mm⁻¹
b = 5.1258 (10) Å	T = 293 K
c = 30.679 (6) Å	0.20 × 0.12 × 0.09 mm

Data collection top

Rigaku R-AXIS RAPID IP area-detector diffractometer	3949 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2946 reflections with I > 2σ(I)
T_min = 0.937, T_max = 0.971	R_int = 0.029
15836 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.110	Δρ_max = 0.34 e Å⁻³
S = 1.13	Δρ_min = −0.35 e Å⁻³
3949 reflections	Absolute structure: Flack (1983), 1304 Friedel pairs
290 parameters	Absolute structure parameter: 0.47 (8)
1 restraint

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
Cl1	0.80437 (6)	0.77974 (17)	0.26938 (4)	0.0660 (3)
Cl2	1.04831 (6)	0.72284 (17)	0.70767 (4)	0.0658 (3)
O1	0.5138 (3)	0.4037 (8)	0.51198 (14)	0.1064 (13)
O2	0.4074 (2)	0.7028 (7)	0.53628 (11)	0.0873 (10)
O3	0.86302 (18)	0.1950 (5)	0.67866 (11)	0.0726 (8)
O4	0.2640 (2)	1.1064 (7)	0.46419 (14)	0.1001 (12)
O5	0.1615 (2)	0.7930 (7)	0.43980 (11)	0.0826 (9)
O6	0.61927 (18)	1.3095 (5)	0.29844 (12)	0.0725 (8)
N1	0.8579 (2)	0.6316 (6)	0.67326 (12)	0.0569 (8)
H1A	0.8872	0.7749	0.6780	0.068*
N2	0.6139 (2)	0.8733 (6)	0.30282 (13)	0.0567 (9)
H2B	0.6428	0.7294	0.2980	0.068*
C1	0.4217 (4)	0.4861 (11)	0.5078 (3)	0.086 (2)
H1B	0.3799	0.3450	0.5154	0.103*
H1C	0.4093	0.5371	0.4779	0.103*
C2	0.6047 (3)	0.9174 (9)	0.60261 (15)	0.0694 (11)
H2A	0.6226	1.0428	0.6228	0.083*
C3	0.5145 (3)	0.9204 (10)	0.58685 (18)	0.0766 (12)
H3A	0.4720	1.0442	0.5964	0.092*
C4	0.4904 (3)	0.7377 (8)	0.55716 (14)	0.0607 (10)
C5	0.5532 (3)	0.5584 (11)	0.5434 (2)	0.0649 (13)
C6	0.6420 (3)	0.5492 (9)	0.5578 (2)	0.0681 (14)
H6A	0.6836	0.4258	0.5473	0.082*
C7	0.6685 (2)	0.7335 (7)	0.58913 (13)	0.0558 (9)
C8	0.7652 (2)	0.7271 (8)	0.60849 (14)	0.0671 (11)
H8A	0.8034	0.6082	0.5917	0.080*
H8B	0.7925	0.8996	0.6064	0.080*
C9	0.7648 (3)	0.6432 (7)	0.65481 (14)	0.0605 (10)
H9A	0.7277	0.7642	0.6717	0.073*
H9B	0.7363	0.4723	0.6569	0.073*
C10	0.8985 (3)	0.4085 (7)	0.68301 (15)	0.0539 (10)
C11	0.9951 (2)	0.4136 (7)	0.70259 (15)	0.0613 (10)
H11A	1.0348	0.3041	0.6848	0.074*
H11B	0.9920	0.3352	0.7313	0.074*
C12	0.1728 (5)	1.0074 (11)	0.4679 (3)	0.088 (2)
H12A	0.1611	0.9539	0.4977	0.105*
H12B	0.1285	1.1426	0.4603	0.105*
C13	0.3619 (3)	0.5967 (9)	0.37410 (14)	0.0662 (11)
H13A	0.3813	0.4735	0.3538	0.079*
C14	0.2717 (3)	0.5835 (10)	0.38929 (18)	0.0748 (12)
H14A	0.2307	0.4562	0.3795	0.090*
C15	0.2458 (3)	0.7656 (8)	0.41918 (13)	0.0605 (10)
C16	0.3067 (3)	0.9502 (10)	0.43397 (19)	0.0592 (12)
C17	0.3958 (3)	0.9658 (9)	0.4176 (2)	0.0668 (15)
H17A	0.4359	1.0969	0.4267	0.080*
C18	0.4239 (3)	0.7821 (7)	0.38744 (12)	0.0560 (9)
C19	0.5200 (3)	0.7908 (9)	0.36873 (14)	0.0670 (11)
H19A	0.5564	0.9174	0.3848	0.080*
H19B	0.5489	0.6214	0.3724	0.080*
C20	0.5208 (2)	0.8615 (7)	0.32136 (14)	0.0602 (10)
H20A	0.4848	0.7339	0.3053	0.072*
H20B	0.4912	1.0299	0.3177	0.072*
C21	0.6554 (2)	1.0929 (7)	0.29311 (13)	0.0506 (9)
C22	0.7510 (3)	1.0888 (7)	0.27470 (15)	0.0627 (10)
H22A	0.7901	1.1967	0.2930	0.075*
H22B	0.7491	1.1696	0.2461	0.075*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0492 (5)	0.0504 (5)	0.0983 (7)	0.0069 (4)	0.0175 (5)	0.0016 (6)
Cl2	0.0504 (5)	0.0516 (5)	0.0956 (7)	−0.0081 (4)	−0.0166 (5)	0.0014 (6)
O1	0.076 (2)	0.131 (3)	0.112 (3)	0.006 (2)	−0.031 (2)	−0.054 (3)
O2	0.0487 (16)	0.124 (3)	0.089 (2)	0.0023 (16)	−0.0162 (16)	0.001 (2)
O3	0.0640 (17)	0.0391 (13)	0.115 (2)	−0.0078 (11)	−0.0205 (16)	−0.0023 (16)
O4	0.075 (2)	0.103 (2)	0.122 (3)	−0.007 (2)	0.037 (2)	−0.041 (3)
O5	0.0531 (16)	0.107 (2)	0.087 (2)	−0.0059 (15)	0.0207 (16)	−0.0081 (19)
O6	0.0626 (17)	0.0394 (13)	0.115 (2)	0.0078 (11)	0.0219 (16)	−0.0040 (16)
N1	0.0437 (16)	0.0416 (16)	0.085 (2)	−0.0045 (13)	−0.0175 (16)	0.0032 (17)
N2	0.0424 (16)	0.0411 (17)	0.087 (3)	0.0053 (13)	0.0127 (16)	−0.0041 (17)
C1	0.066 (3)	0.122 (5)	0.069 (5)	−0.019 (3)	−0.030 (4)	0.005 (3)
C2	0.059 (2)	0.075 (3)	0.074 (3)	0.006 (2)	−0.009 (2)	−0.012 (3)
C3	0.059 (3)	0.090 (3)	0.080 (3)	0.026 (2)	−0.005 (3)	−0.013 (3)
C4	0.042 (2)	0.081 (3)	0.058 (2)	−0.0002 (19)	−0.0040 (17)	0.007 (2)
C5	0.055 (3)	0.072 (2)	0.067 (3)	−0.007 (2)	−0.005 (2)	−0.010 (3)
C6	0.053 (3)	0.078 (3)	0.073 (4)	0.009 (2)	−0.004 (2)	−0.010 (3)
C7	0.0438 (18)	0.068 (2)	0.056 (2)	−0.0028 (17)	−0.0025 (17)	0.004 (2)
C8	0.042 (2)	0.093 (3)	0.067 (3)	−0.0042 (18)	−0.0033 (17)	−0.001 (2)
C9	0.040 (2)	0.057 (2)	0.085 (3)	−0.0035 (15)	−0.0128 (17)	0.007 (2)
C10	0.052 (2)	0.039 (2)	0.071 (3)	−0.0008 (17)	0.001 (2)	−0.001 (2)
C11	0.0459 (19)	0.0435 (19)	0.094 (3)	0.0010 (15)	−0.016 (2)	0.005 (2)
C12	0.072 (4)	0.103 (5)	0.087 (6)	0.010 (2)	0.007 (4)	0.003 (3)
C13	0.061 (3)	0.069 (3)	0.068 (3)	−0.005 (2)	0.013 (2)	−0.005 (3)
C14	0.065 (3)	0.086 (3)	0.074 (3)	−0.025 (2)	0.012 (2)	−0.008 (3)
C15	0.046 (2)	0.075 (2)	0.061 (3)	0.0012 (19)	0.0091 (17)	0.010 (2)
C16	0.053 (3)	0.067 (2)	0.058 (3)	0.003 (2)	0.009 (2)	−0.001 (2)
C17	0.057 (3)	0.074 (3)	0.070 (4)	−0.011 (2)	0.012 (3)	−0.012 (2)
C18	0.049 (2)	0.066 (2)	0.054 (2)	0.0020 (17)	0.0007 (18)	0.0051 (19)
C19	0.044 (2)	0.088 (3)	0.068 (3)	0.001 (2)	0.0021 (17)	−0.003 (2)
C20	0.040 (2)	0.060 (2)	0.080 (3)	0.0049 (16)	0.0119 (17)	0.006 (2)
C21	0.0473 (19)	0.038 (2)	0.067 (2)	0.0004 (15)	0.0091 (19)	−0.002 (2)
C22	0.054 (2)	0.0424 (19)	0.092 (3)	0.0005 (16)	0.015 (2)	−0.003 (2)

Geometric parameters (Å, º) top

Cl1—C22	1.769 (4)	C7—C8	1.517 (5)
Cl2—C11	1.768 (4)	C8—C9	1.485 (6)
O1—C5	1.372 (7)	C8—H8A	0.9700
O1—C1	1.401 (7)	C8—H8B	0.9700
O2—C4	1.370 (5)	C9—H9A	0.9700
O2—C1	1.428 (7)	C9—H9B	0.9700
O3—C10	1.216 (4)	C10—C11	1.518 (5)
O4—C16	1.371 (6)	C11—H11A	0.9700
O4—C12	1.416 (7)	C11—H11B	0.9700
O5—C15	1.378 (5)	C12—H12A	0.9700
O5—C12	1.405 (7)	C12—H12B	0.9700
O6—C21	1.237 (4)	C13—C18	1.367 (6)
N1—C10	1.319 (5)	C13—C14	1.384 (6)
N1—C9	1.458 (4)	C13—H13A	0.9300
N1—H1A	0.8600	C14—C15	1.361 (6)
N2—C21	1.309 (5)	C14—H14A	0.9300
N2—C20	1.459 (4)	C15—C16	1.368 (6)
N2—H2B	0.8600	C16—C17	1.383 (6)
C1—H1B	0.9700	C17—C18	1.381 (6)
C1—H1C	0.9700	C17—H17A	0.9300
C2—C7	1.381 (6)	C18—C19	1.501 (5)
C2—C3	1.388 (6)	C19—C20	1.498 (6)
C2—H2A	0.9300	C19—H19A	0.9700
C3—C4	1.352 (7)	C19—H19B	0.9700
C3—H3A	0.9300	C20—H20A	0.9700
C4—C5	1.358 (7)	C20—H20B	0.9700
C5—C6	1.355 (6)	C21—C22	1.491 (5)
C6—C7	1.401 (7)	C22—H22A	0.9700
C6—H6A	0.9300	C22—H22B	0.9700

C5—O1—C1	106.5 (4)	C10—C11—H11A	108.1
C4—O2—C1	105.1 (4)	Cl2—C11—H11A	108.1
C16—O4—C12	105.2 (4)	C10—C11—H11B	108.1
C15—O5—C12	105.0 (4)	Cl2—C11—H11B	108.1
C10—N1—C9	122.2 (3)	H11A—C11—H11B	107.3
C10—N1—H1A	118.9	O5—C12—O4	109.8 (6)
C9—N1—H1A	118.9	O5—C12—H12A	109.7
C21—N2—C20	123.0 (3)	O4—C12—H12A	109.7
C21—N2—H2B	118.5	O5—C12—H12B	109.7
C20—N2—H2B	118.5	O4—C12—H12B	109.7
O1—C1—O2	108.4 (5)	H12A—C12—H12B	108.2
O1—C1—H1B	110.0	C18—C13—C14	123.2 (4)
O2—C1—H1B	110.0	C18—C13—H13A	118.4
O1—C1—H1C	110.0	C14—C13—H13A	118.4
O2—C1—H1C	110.0	C15—C14—C13	116.8 (4)
H1B—C1—H1C	108.4	C15—C14—H14A	121.6
C7—C2—C3	121.8 (4)	C13—C14—H14A	121.6
C7—C2—H2A	119.1	C14—C15—C16	121.4 (4)
C3—C2—H2A	119.1	C14—C15—O5	128.4 (4)
C4—C3—C2	117.9 (4)	C16—C15—O5	110.1 (4)
C4—C3—H3A	121.0	C15—C16—O4	109.9 (4)
C2—C3—H3A	121.0	C15—C16—C17	121.1 (5)
C3—C4—C5	120.4 (4)	O4—C16—C17	129.0 (5)
C3—C4—O2	129.1 (4)	C18—C17—C16	118.5 (4)
C5—C4—O2	110.5 (4)	C18—C17—H17A	120.8
C6—C5—C4	123.6 (5)	C16—C17—H17A	120.8
C6—C5—O1	126.9 (5)	C13—C18—C17	118.9 (4)
C4—C5—O1	109.4 (4)	C13—C18—C19	120.7 (4)
C5—C6—C7	117.2 (5)	C17—C18—C19	120.4 (4)
C5—C6—H6A	121.4	C20—C19—C18	112.7 (3)
C7—C6—H6A	121.4	C20—C19—H19A	109.0
C2—C7—C6	119.0 (4)	C18—C19—H19A	109.0
C2—C7—C8	120.7 (4)	C20—C19—H19B	109.0
C6—C7—C8	120.3 (4)	C18—C19—H19B	109.0
C9—C8—C7	112.2 (3)	H19A—C19—H19B	107.8
C9—C8—H8A	109.2	N2—C20—C19	113.3 (3)
C7—C8—H8A	109.2	N2—C20—H20A	108.9
C9—C8—H8B	109.2	C19—C20—H20A	108.9
C7—C8—H8B	109.2	N2—C20—H20B	108.9
H8A—C8—H8B	107.9	C19—C20—H20B	108.9
N1—C9—C8	112.4 (3)	H20A—C20—H20B	107.7
N1—C9—H9A	109.1	O6—C21—N2	123.3 (3)
C8—C9—H9A	109.1	O6—C21—C22	116.9 (3)
N1—C9—H9B	109.1	N2—C21—C22	119.8 (3)
C8—C9—H9B	109.1	C21—C22—Cl1	116.8 (3)
H9A—C9—H9B	107.9	C21—C22—H22A	108.1
O3—C10—N1	124.7 (4)	Cl1—C22—H22A	108.1
O3—C10—C11	116.4 (3)	C21—C22—H22B	108.1
N1—C10—C11	118.9 (3)	Cl1—C22—H22B	108.1
C10—C11—Cl2	116.7 (3)	H22A—C22—H22B	107.3

C5—O1—C1—O2	2.5 (7)	C15—O5—C12—O4	−0.5 (7)
C4—O2—C1—O1	−1.5 (6)	C16—O4—C12—O5	0.0 (7)
C7—C2—C3—C4	−0.7 (8)	C18—C13—C14—C15	−0.5 (7)
C2—C3—C4—C5	−0.2 (8)	C13—C14—C15—C16	−1.0 (7)
C2—C3—C4—O2	−178.6 (4)	C13—C14—C15—O5	−178.8 (4)
C1—O2—C4—C3	178.5 (6)	C12—O5—C15—C14	178.8 (6)
C1—O2—C4—C5	−0.1 (5)	C12—O5—C15—C16	0.8 (5)
C3—C4—C5—C6	−0.2 (9)	C14—C15—C16—O4	−179.0 (5)
O2—C4—C5—C6	178.5 (5)	O5—C15—C16—O4	−0.9 (6)
C3—C4—C5—O1	−177.1 (5)	C14—C15—C16—C17	2.9 (8)
O2—C4—C5—O1	1.6 (6)	O5—C15—C16—C17	−178.9 (5)
C1—O1—C5—C6	−179.3 (6)	C12—O4—C16—C15	0.5 (7)
C1—O1—C5—C4	−2.5 (7)	C12—O4—C16—C17	178.4 (6)
C4—C5—C6—C7	1.3 (9)	C15—C16—C17—C18	−3.2 (9)
O1—C5—C6—C7	177.6 (6)	O4—C16—C17—C18	179.1 (5)
C3—C2—C7—C6	1.7 (7)	C14—C13—C18—C17	0.1 (7)
C3—C2—C7—C8	−177.1 (5)	C14—C13—C18—C19	−178.2 (4)
C5—C6—C7—C2	−2.0 (8)	C16—C17—C18—C13	1.7 (8)
C5—C6—C7—C8	176.9 (5)	C16—C17—C18—C19	180.0 (5)
C2—C7—C8—C9	69.1 (5)	C13—C18—C19—C20	66.7 (5)
C6—C7—C8—C9	−109.7 (5)	C17—C18—C19—C20	−111.5 (5)
C10—N1—C9—C8	−109.7 (5)	C21—N2—C20—C19	−106.4 (5)
C7—C8—C9—N1	178.8 (3)	C18—C19—C20—N2	179.4 (3)
C9—N1—C10—O3	−1.6 (6)	C20—N2—C21—O6	−0.6 (6)
C9—N1—C10—C11	−179.3 (4)	C20—N2—C21—C22	179.3 (4)
O3—C10—C11—Cl2	178.4 (3)	O6—C21—C22—Cl1	177.3 (3)
N1—C10—C11—Cl2	−3.7 (6)	N2—C21—C22—Cl1	−2.6 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3ⁱ	0.86	2.18	2.894 (4)	140
N2—H2B···O6ⁱⁱ	0.86	2.18	2.894 (4)	140

Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₂ClNO₃
M_r	241.67
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	293
a, b, c (Å)	14.429 (3), 5.1258 (10), 30.679 (6)
V (Å³)	2269.1 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.20 × 0.12 × 0.09

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.937, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	15836, 3949, 2946
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.110, 1.13
No. of reflections	3949
No. of parameters	290
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.35
Absolute structure	Flack (1983), 1304 Friedel pairs
Absolute structure parameter	0.47 (8)

Computer programs: RAPID-AUTO (Rigaku, 2004), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3ⁱ	0.86	2.18	2.894 (4)	140.0
N2—H2B···O6ⁱⁱ	0.86	2.18	2.894 (4)	140.4

Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bernhard, H. O. & Snieckus, V. (1971). Tetrahedron, 27, 2091–2100. CrossRef CAS Web of Science Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Kuehne, M. E., Bornmann, W. G., Parsons, W. H., Spitzer, T. D., Blount, J. F. & Zubieta, J. (1988). J. Org. Chem. 53, 3439–3450. CSD CrossRef CAS Web of Science Google Scholar
Ma, C., Liu, S., Xin, L., Zhang, Q., Ding, K., Falck, J. R. & Shin, D. (2006). Chem. Lett. 35, 1010–1011. Web of Science CrossRef CAS Google Scholar
Rigaku (2004). RAPID-AUTO. Rigaku Corporation, Takyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 6| June 2008| Page o1118

doi:10.1107/S1600536808014232

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