Methyl 4-(3-chloro­prop­oxy)-5-meth­oxy-2-nitro­benzoate

Zhang, M.; Lu, R.; Han, L.; Wei, W.; Wang, H.

doi:10.1107/S1600536809009076

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o781

doi:10.1107/S1600536809009076

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Methyl 4-(3-chloropropoxy)-5-methoxy-2-nitrobenzoate

Min Zhang,^a,^b Ran-zhe Lu,^a,^b Lu-na Han,^a,^b Wen-bin Wei ^a,^b and Hai-bo Wang ^a ^*

^aCollege of Light Industry and Food Science, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China, and ^bCollege of Science, and College of Light Industry and Food Science, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: wanghaibo@njut.edu.cn

(Received 9 March 2009; accepted 12 March 2009; online 19 March 2009)

The asymmetric unit of the title compound, C₁₂H₁₄ClNO₆, contains two crystallographically independent molecules, in which the benzene rings are oriented at a dihedral angle of 9.12 (3)°. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds link the molecules into a three-dimensional network.

Related literature

For general background, see: Knesl et al. (2006 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₂H₁₄ClNO₆
M_r = 303.69
Monoclinic, P 2₁ /c
a = 23.150 (5) Å
b = 15.013 (3) Å
c = 8.0700 (16) Å
β = 93.42 (3)°
V = 2799.7 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 294 K
0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.916, T_max = 0.943
5208 measured reflections
5096 independent reflections
2874 reflections with I > 2σ(I)
R_int = 0.038
3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.162
S = 1.03
5096 reflections
362 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯O4ⁱ	0.97	2.58	3.336 (7)	135
C13—H13B⋯O9ⁱⁱ	0.96	2.41	3.211 (6)	141
C21—H21A⋯O5ⁱⁱⁱ	0.96	2.48	3.243 (5)	136
C24—H24A⋯O9^iv	0.97	2.59	3.276 (6)	128
Symmetry codes: (i) -x, -y+1, -z; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) x, y, z+1; (iv) -x+1, -y+1, -z+1.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); 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: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009076/hk2642sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809009076/hk2642Isup2.hkl

checkCIF report

Comment top

As part of our ongoing studies on quinazoline derivatives (Knesl et al., 2006), we report herein the crystal structure of the title compound.

The asymmetric unit of the title compound contains two crystallographically independent molecules (Fig. 1), in which the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C3-C8) and A' (C15-C20) are, of course, planar and they are oriented at a dihedral angle of A/A' = 9.12 (3)°.

In the crystal structure, weak intermolecular C-H···O hydrogen bonds (Table 1) link the molecules into a three dimensional network (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For general background, see: Knesl et al. (2006). For bond-length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, a solution of methyl 4-(3-chloro- propoxy)-3-methoxybenzoate (19 mmol) in acetic acid (20 ml) was added dropwise to nitric acid (98%, 4.5 ml) at 273-278 K. The mixture was stirred for 1 h at room temperature, and then for 2 h at 323 K. After the reaction was completed, the reaction mixture was poured into ice/water (130 ml), and then extracted with trichloromethane (20 ml). The combined organic phases were collected, washed with saturated sodium bicarbonate (20 ml), brine (20 ml), dried (Na₂SO₄) and decolorized (charcoal). Trichloromethane was then removed under reduced pressure to give a yellow oil, which was crystallized from ethyl acetate/petroleum ether to afford the product as light yellow crystals (m.p. 337 K). Crystals suitable for X-ray analysis were obtained by slow evaporation of a methanol solution.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); 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: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonding are omitted.

Methyl 4-(3-chloropropoxy)-5-methoxy-2-nitrobenzoate top

Crystal data top

C₁₂H₁₄ClNO₆	F(000) = 1264
M_r = 303.69	D_x = 1.441 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 337 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 23.150 (5) Å	Cell parameters from 25 reflections
b = 15.013 (3) Å	θ = 10–13°
c = 8.0700 (16) Å	µ = 0.30 mm⁻¹
β = 93.42 (3)°	T = 294 K
V = 2799.7 (10) Å³	Needle, yellow
Z = 8	0.30 × 0.20 × 0.20 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2874 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.038
Graphite monochromator	θ_max = 25.3°, θ_min = 1.6°
ω/2θ scans	h = 0→27
Absorption correction: ψ scan (North et al., 1968)	k = 0→18
T_min = 0.916, T_max = 0.943	l = −9→9
5208 measured reflections	3 standard reflections every 120 min
5096 independent reflections	intensity decay: 1%

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)] = 0.065	H-atom parameters constrained
wR(F²) = 0.162	w = 1/[σ²(F_o²) + (0.0567P)² + 1.915P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
5096 reflections	Δρ_max = 0.40 e Å⁻³
362 parameters	Δρ_min = −0.30 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: 0.0049 (6)

Crystal data top

C₁₂H₁₄ClNO₆	V = 2799.7 (10) Å³
M_r = 303.69	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 23.150 (5) Å	µ = 0.30 mm⁻¹
b = 15.013 (3) Å	T = 294 K
c = 8.0700 (16) Å	0.30 × 0.20 × 0.20 mm
β = 93.42 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2874 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.038
T_min = 0.916, T_max = 0.943	3 standard reflections every 120 min
5208 measured reflections	intensity decay: 1%
5096 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.162	H-atom parameters constrained
S = 1.03	Δρ_max = 0.40 e Å⁻³
5096 reflections	Δρ_min = −0.30 e Å⁻³
362 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.26534 (6)	0.48992 (8)	0.29390 (17)	0.0758 (4)
Cl2	0.30461 (6)	0.79461 (8)	0.6560 (2)	0.0888 (5)
O1	−0.10537 (13)	0.2705 (2)	0.1972 (5)	0.0846 (11)
O2	−0.05735 (14)	0.1596 (2)	0.3282 (4)	0.0714 (9)
O3	−0.06317 (19)	0.3963 (3)	0.4296 (5)	0.1081 (15)
O4	−0.05061 (16)	0.5014 (2)	0.2559 (6)	0.0970 (13)
O5	0.13459 (12)	0.23218 (18)	0.0445 (4)	0.0559 (8)
O6	0.14060 (12)	0.40304 (18)	0.0445 (4)	0.0593 (8)
O7	0.40610 (12)	0.06586 (17)	0.5910 (4)	0.0558 (8)
O8	0.48185 (14)	0.1024 (2)	0.7607 (4)	0.0740 (10)
O9	0.53876 (12)	0.3392 (2)	0.6019 (4)	0.0637 (9)
O10	0.51561 (13)	0.2122 (2)	0.4944 (4)	0.0694 (9)
O11	0.28231 (11)	0.33078 (17)	0.7787 (4)	0.0528 (7)
O12	0.34201 (12)	0.46634 (17)	0.7009 (4)	0.0538 (8)
N1	−0.04080 (17)	0.4270 (3)	0.3109 (6)	0.0687 (11)
N2	0.50447 (14)	0.2793 (2)	0.5715 (4)	0.0466 (8)
C1	−0.1592 (2)	0.2271 (5)	0.2275 (9)	0.124 (3)
H1A	−0.1907	0.2607	0.1761	0.185*
H1B	−0.1635	0.2237	0.3449	0.185*
H1C	−0.1593	0.1681	0.1816	0.185*
C2	−0.05727 (18)	0.2299 (3)	0.2610 (6)	0.0554 (11)
C3	−0.00469 (17)	0.2813 (3)	0.2209 (5)	0.0477 (10)
C4	0.00118 (18)	0.3722 (3)	0.2282 (5)	0.0495 (10)
C5	0.04788 (18)	0.4163 (3)	0.1691 (5)	0.0542 (11)
H5A	0.0498	0.4781	0.1724	0.065*
C6	0.09190 (17)	0.3675 (3)	0.1046 (5)	0.0474 (10)
C7	0.08873 (17)	0.2742 (3)	0.1040 (5)	0.0463 (10)
C8	0.04040 (17)	0.2321 (3)	0.1598 (5)	0.0476 (10)
H8A	0.0380	0.1702	0.1564	0.057*
C9	0.1376 (2)	0.1372 (3)	0.0606 (6)	0.0626 (12)
H9A	0.1721	0.1159	0.0133	0.094*
H9B	0.1043	0.1109	0.0033	0.094*
H9C	0.1384	0.1213	0.1759	0.094*
C10	0.1491 (2)	0.4975 (3)	0.0631 (7)	0.0645 (13)
H10A	0.1494	0.5140	0.1794	0.077*
H10B	0.1182	0.5297	0.0031	0.077*
C11	0.2060 (2)	0.5190 (3)	−0.0057 (6)	0.0638 (13)
H11A	0.2128	0.5825	0.0057	0.077*
H11B	0.2037	0.5053	−0.1234	0.077*
C12	0.25688 (19)	0.4705 (3)	0.0750 (6)	0.0612 (12)
H12A	0.2918	0.4893	0.0241	0.073*
H12B	0.2521	0.4071	0.0553	0.073*
C13	0.4229 (2)	−0.0264 (3)	0.6021 (7)	0.0748 (15)
H13A	0.3962	−0.0617	0.5344	0.112*
H13B	0.4226	−0.0458	0.7154	0.112*
H13C	0.4611	−0.0332	0.5638	0.112*
C14	0.43940 (17)	0.1222 (3)	0.6788 (5)	0.0433 (10)
C15	0.41457 (15)	0.2145 (2)	0.6687 (4)	0.0367 (9)
C16	0.35887 (16)	0.2280 (2)	0.7183 (5)	0.0409 (9)
H16A	0.3365	0.1790	0.7442	0.049*
C17	0.33587 (16)	0.3122 (2)	0.7300 (5)	0.0397 (9)
C18	0.36847 (16)	0.3871 (2)	0.6871 (5)	0.0415 (9)
C19	0.42370 (16)	0.3744 (2)	0.6376 (5)	0.0418 (9)
H19A	0.4460	0.4231	0.6098	0.050*
C20	0.44601 (15)	0.2890 (2)	0.6293 (4)	0.0378 (9)
C21	0.24745 (17)	0.2586 (3)	0.8302 (5)	0.0521 (11)
H21A	0.2108	0.2811	0.8613	0.078*
H21B	0.2667	0.2292	0.9235	0.078*
H21C	0.2414	0.2171	0.7404	0.078*
C22	0.3705 (2)	0.5435 (3)	0.6460 (6)	0.0567 (11)
H22A	0.3781	0.5384	0.5295	0.068*
H22B	0.4070	0.5523	0.7096	0.068*
C23	0.3290 (2)	0.6207 (3)	0.6738 (7)	0.0680 (14)
H23A	0.2931	0.6108	0.6080	0.082*
H23B	0.3201	0.6222	0.7897	0.082*
C24	0.3531 (2)	0.7046 (3)	0.6292 (8)	0.0895 (18)
H24A	0.3629	0.7024	0.5141	0.107*
H24B	0.3885	0.7149	0.6969	0.107*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0858 (9)	0.0698 (8)	0.0709 (8)	−0.0107 (7)	−0.0018 (7)	−0.0109 (7)
Cl2	0.0811 (9)	0.0518 (7)	0.1376 (13)	0.0225 (6)	0.0417 (9)	0.0179 (8)
O1	0.049 (2)	0.095 (3)	0.111 (3)	−0.0011 (18)	0.0157 (19)	0.046 (2)
O2	0.071 (2)	0.066 (2)	0.079 (2)	−0.0029 (17)	0.0184 (18)	0.0170 (19)
O3	0.124 (3)	0.119 (3)	0.087 (3)	0.048 (3)	0.053 (3)	0.017 (3)
O4	0.088 (3)	0.059 (2)	0.148 (4)	0.018 (2)	0.037 (2)	0.006 (2)
O5	0.0529 (18)	0.0488 (17)	0.068 (2)	−0.0020 (14)	0.0179 (15)	−0.0026 (15)
O6	0.0515 (18)	0.0475 (17)	0.080 (2)	−0.0126 (14)	0.0128 (16)	−0.0039 (15)
O7	0.0585 (18)	0.0382 (15)	0.069 (2)	0.0053 (14)	−0.0072 (15)	−0.0044 (15)
O8	0.064 (2)	0.064 (2)	0.089 (2)	0.0219 (17)	−0.0301 (19)	−0.0083 (18)
O9	0.0436 (17)	0.071 (2)	0.078 (2)	−0.0114 (16)	0.0142 (15)	−0.0192 (17)
O10	0.062 (2)	0.060 (2)	0.089 (2)	0.0059 (16)	0.0290 (18)	−0.0250 (18)
O11	0.0425 (16)	0.0458 (16)	0.072 (2)	0.0063 (13)	0.0190 (14)	−0.0015 (15)
O12	0.0547 (18)	0.0370 (15)	0.072 (2)	0.0082 (13)	0.0231 (15)	0.0010 (14)
N1	0.062 (3)	0.070 (3)	0.075 (3)	0.008 (2)	0.011 (2)	0.000 (2)
N2	0.041 (2)	0.051 (2)	0.049 (2)	0.0044 (17)	0.0083 (16)	−0.0039 (18)
C1	0.048 (3)	0.155 (6)	0.171 (7)	−0.014 (4)	0.023 (4)	0.067 (5)
C2	0.048 (3)	0.068 (3)	0.052 (3)	0.001 (2)	0.014 (2)	0.001 (2)
C3	0.044 (2)	0.056 (3)	0.043 (2)	0.004 (2)	0.0049 (19)	0.001 (2)
C4	0.046 (2)	0.055 (3)	0.048 (3)	0.005 (2)	0.005 (2)	−0.008 (2)
C5	0.052 (3)	0.045 (2)	0.065 (3)	−0.001 (2)	−0.003 (2)	−0.003 (2)
C6	0.043 (2)	0.051 (3)	0.048 (3)	−0.005 (2)	0.000 (2)	−0.001 (2)
C7	0.048 (3)	0.046 (2)	0.044 (2)	−0.002 (2)	0.000 (2)	−0.006 (2)
C8	0.050 (3)	0.044 (2)	0.049 (3)	−0.005 (2)	0.006 (2)	0.001 (2)
C9	0.063 (3)	0.049 (3)	0.078 (3)	−0.001 (2)	0.017 (2)	−0.006 (2)
C10	0.060 (3)	0.042 (2)	0.092 (4)	−0.007 (2)	0.002 (3)	0.003 (2)
C11	0.073 (3)	0.047 (3)	0.071 (3)	−0.014 (2)	0.004 (3)	0.005 (2)
C12	0.058 (3)	0.059 (3)	0.067 (3)	−0.009 (2)	0.013 (2)	−0.007 (2)
C13	0.082 (4)	0.036 (2)	0.106 (4)	0.005 (2)	0.001 (3)	0.000 (3)
C14	0.044 (2)	0.046 (2)	0.041 (2)	0.004 (2)	0.0054 (19)	−0.0019 (19)
C15	0.038 (2)	0.039 (2)	0.033 (2)	0.0017 (17)	0.0013 (17)	−0.0016 (17)
C16	0.041 (2)	0.036 (2)	0.046 (2)	−0.0013 (17)	0.0048 (18)	0.0002 (18)
C17	0.036 (2)	0.044 (2)	0.040 (2)	0.0053 (18)	0.0084 (17)	−0.0025 (18)
C18	0.046 (2)	0.039 (2)	0.041 (2)	0.0089 (19)	0.0060 (18)	−0.0043 (18)
C19	0.049 (2)	0.039 (2)	0.039 (2)	−0.0025 (18)	0.0081 (18)	−0.0030 (18)
C20	0.035 (2)	0.044 (2)	0.035 (2)	0.0052 (17)	0.0059 (16)	−0.0034 (17)
C21	0.046 (2)	0.058 (3)	0.053 (3)	−0.004 (2)	0.013 (2)	−0.004 (2)
C22	0.068 (3)	0.040 (2)	0.063 (3)	0.007 (2)	0.016 (2)	0.001 (2)
C23	0.074 (3)	0.046 (3)	0.087 (4)	0.006 (2)	0.030 (3)	−0.001 (3)
C24	0.080 (4)	0.061 (3)	0.131 (5)	0.013 (3)	0.036 (4)	−0.002 (3)

Geometric parameters (Å, º) top

Cl1—C12	1.789 (5)	C9—H9A	0.9600
Cl2—C24	1.778 (5)	C9—H9B	0.9600
O1—C2	1.345 (5)	C9—H9C	0.9600
O1—C1	1.439 (5)	C10—C11	1.496 (6)
O2—C2	1.187 (5)	C10—H10A	0.9700
O3—N1	1.208 (5)	C10—H10B	0.9700
O4—N1	1.218 (5)	C11—C12	1.500 (6)
O5—C7	1.348 (5)	C11—H11A	0.9700
O5—C9	1.433 (5)	C11—H11B	0.9700
O6—C6	1.363 (4)	C12—H12A	0.9700
O6—C10	1.438 (5)	C12—H12B	0.9700
O7—C14	1.322 (5)	C13—H13A	0.9600
O7—C13	1.440 (5)	C13—H13B	0.9600
O8—C14	1.189 (4)	C13—H13C	0.9600
O9—N2	1.215 (4)	C14—C15	1.501 (5)
O10—N2	1.220 (4)	C15—C20	1.382 (5)
O11—C17	1.352 (4)	C15—C16	1.388 (5)
O11—C21	1.427 (4)	C16—C17	1.377 (5)
O12—C18	1.346 (4)	C16—H16A	0.9300
O12—C22	1.417 (5)	C17—C18	1.409 (5)
N1—C4	1.464 (5)	C18—C19	1.375 (5)
N2—C20	1.465 (5)	C19—C20	1.385 (5)
C1—H1A	0.9600	C19—H19A	0.9300
C1—H1B	0.9600	C21—H21A	0.9600
C1—H1C	0.9600	C21—H21B	0.9600
C2—C3	1.493 (6)	C21—H21C	0.9600
C3—C4	1.372 (5)	C22—C23	1.530 (5)
C3—C8	1.393 (5)	C22—H22A	0.9700
C4—C5	1.377 (6)	C22—H22B	0.9700
C5—C6	1.381 (5)	C23—C24	1.432 (6)
C5—H5A	0.9300	C23—H23A	0.9700
C6—C7	1.402 (5)	C23—H23B	0.9700
C7—C8	1.384 (5)	C24—H24A	0.9700
C8—H8A	0.9300	C24—H24B	0.9700

C2—O1—C1	115.8 (4)	C11—C12—Cl1	112.7 (3)
C7—O5—C9	118.0 (3)	C11—C12—H12A	109.0
C6—O6—C10	117.4 (3)	Cl1—C12—H12A	109.0
C14—O7—C13	115.8 (3)	C11—C12—H12B	109.0
C17—O11—C21	118.2 (3)	Cl1—C12—H12B	109.0
C18—O12—C22	118.3 (3)	H12A—C12—H12B	107.8
O3—N1—O4	124.0 (4)	O7—C13—H13A	109.5
O3—N1—C4	118.3 (4)	O7—C13—H13B	109.5
O4—N1—C4	117.6 (4)	H13A—C13—H13B	109.5
O9—N2—O10	124.0 (3)	O7—C13—H13C	109.5
O9—N2—C20	117.9 (3)	H13A—C13—H13C	109.5
O10—N2—C20	118.2 (3)	H13B—C13—H13C	109.5
O1—C1—H1A	109.5	O8—C14—O7	125.0 (4)
O1—C1—H1B	109.5	O8—C14—C15	124.2 (4)
H1A—C1—H1B	109.5	O7—C14—C15	110.7 (3)
O1—C1—H1C	109.5	C20—C15—C16	117.3 (3)
H1A—C1—H1C	109.5	C20—C15—C14	123.7 (3)
H1B—C1—H1C	109.5	C16—C15—C14	118.6 (3)
O2—C2—O1	123.7 (4)	C17—C16—C15	121.6 (3)
O2—C2—C3	125.6 (4)	C17—C16—H16A	119.2
O1—C2—C3	110.5 (4)	C15—C16—H16A	119.2
C4—C3—C8	118.0 (4)	O11—C17—C16	125.1 (3)
C4—C3—C2	125.8 (4)	O11—C17—C18	114.9 (3)
C8—C3—C2	116.1 (4)	C16—C17—C18	120.0 (3)
C3—C4—C5	122.7 (4)	O12—C18—C19	125.6 (4)
C3—C4—N1	120.8 (4)	O12—C18—C17	115.6 (3)
C5—C4—N1	116.4 (4)	C19—C18—C17	118.8 (3)
C4—C5—C6	119.2 (4)	C18—C19—C20	119.8 (3)
C4—C5—H5A	120.4	C18—C19—H19A	120.1
C6—C5—H5A	120.4	C20—C19—H19A	120.1
O6—C6—C5	124.9 (4)	C15—C20—C19	122.3 (3)
O6—C6—C7	115.7 (4)	C15—C20—N2	120.1 (3)
C5—C6—C7	119.4 (4)	C19—C20—N2	117.5 (3)
O5—C7—C8	124.8 (4)	O11—C21—H21A	109.5
O5—C7—C6	115.3 (3)	O11—C21—H21B	109.5
C8—C7—C6	119.9 (4)	H21A—C21—H21B	109.5
C7—C8—C3	120.6 (4)	O11—C21—H21C	109.5
C7—C8—H8A	119.7	H21A—C21—H21C	109.5
C3—C8—H8A	119.7	H21B—C21—H21C	109.5
O5—C9—H9A	109.5	O12—C22—C23	105.3 (3)
O5—C9—H9B	109.5	O12—C22—H22A	110.7
H9A—C9—H9B	109.5	C23—C22—H22A	110.7
O5—C9—H9C	109.5	O12—C22—H22B	110.7
H9A—C9—H9C	109.5	C23—C22—H22B	110.7
H9B—C9—H9C	109.5	H22A—C22—H22B	108.8
O6—C10—C11	107.0 (4)	C24—C23—C22	111.8 (4)
O6—C10—H10A	110.3	C24—C23—H23A	109.2
C11—C10—H10A	110.3	C22—C23—H23A	109.2
O6—C10—H10B	110.3	C24—C23—H23B	109.2
C11—C10—H10B	110.3	C22—C23—H23B	109.2
H10A—C10—H10B	108.6	H23A—C23—H23B	107.9
C10—C11—C12	114.8 (4)	C23—C24—Cl2	112.4 (4)
C10—C11—H11A	108.6	C23—C24—H24A	109.1
C12—C11—H11A	108.6	Cl2—C24—H24A	109.1
C10—C11—H11B	108.6	C23—C24—H24B	109.1
C12—C11—H11B	108.6	Cl2—C24—H24B	109.1
H11A—C11—H11B	107.5	H24A—C24—H24B	107.9

C1—O1—C2—O2	5.3 (7)	C13—O7—C14—O8	1.8 (6)
C1—O1—C2—C3	179.9 (5)	C13—O7—C14—C15	−175.1 (3)
O2—C2—C3—C4	−143.1 (5)	O8—C14—C15—C20	53.4 (6)
O1—C2—C3—C4	42.5 (6)	O7—C14—C15—C20	−129.7 (4)
O2—C2—C3—C8	41.7 (6)	O8—C14—C15—C16	−119.6 (5)
O1—C2—C3—C8	−132.8 (4)	O7—C14—C15—C16	57.4 (5)
C8—C3—C4—C5	3.9 (6)	C20—C15—C16—C17	−0.8 (5)
C2—C3—C4—C5	−171.3 (4)	C14—C15—C16—C17	172.6 (4)
C8—C3—C4—N1	−171.9 (4)	C21—O11—C17—C16	3.3 (6)
C2—C3—C4—N1	12.9 (7)	C21—O11—C17—C18	−177.7 (3)
O3—N1—C4—C3	33.0 (7)	C15—C16—C17—O11	−179.4 (3)
O4—N1—C4—C3	−147.6 (4)	C15—C16—C17—C18	1.6 (6)
O3—N1—C4—C5	−143.1 (5)	C22—O12—C18—C19	6.2 (6)
O4—N1—C4—C5	36.3 (6)	C22—O12—C18—C17	−174.6 (4)
C3—C4—C5—C6	−2.3 (7)	O11—C17—C18—O12	0.2 (5)
N1—C4—C5—C6	173.7 (4)	C16—C17—C18—O12	179.3 (3)
C10—O6—C6—C5	5.8 (6)	O11—C17—C18—C19	179.4 (3)
C10—O6—C6—C7	−172.0 (4)	C16—C17—C18—C19	−1.5 (6)
C4—C5—C6—O6	−179.1 (4)	O12—C18—C19—C20	179.7 (4)
C4—C5—C6—C7	−1.4 (6)	C17—C18—C19—C20	0.6 (6)
C9—O5—C7—C8	−9.0 (6)	C16—C15—C20—C19	−0.2 (5)
C9—O5—C7—C6	172.0 (4)	C14—C15—C20—C19	−173.2 (4)
O6—C6—C7—O5	0.3 (5)	C16—C15—C20—N2	−178.3 (3)
C5—C6—C7—O5	−177.6 (4)	C14—C15—C20—N2	8.7 (6)
O6—C6—C7—C8	−178.8 (3)	C18—C19—C20—C15	0.3 (6)
C5—C6—C7—C8	3.3 (6)	C18—C19—C20—N2	178.4 (3)
O5—C7—C8—C3	179.3 (4)	O9—N2—C20—C15	−150.4 (4)
C6—C7—C8—C3	−1.7 (6)	O10—N2—C20—C15	30.4 (5)
C4—C3—C8—C7	−1.8 (6)	O9—N2—C20—C19	31.4 (5)
C2—C3—C8—C7	173.8 (4)	O10—N2—C20—C19	−147.8 (4)
C6—O6—C10—C11	177.8 (4)	C18—O12—C22—C23	178.5 (4)
O6—C10—C11—C12	−58.2 (5)	O12—C22—C23—C24	177.8 (5)
C10—C11—C12—Cl1	−57.8 (5)	C22—C23—C24—Cl2	178.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O4ⁱ	0.97	2.58	3.336 (7)	135
C13—H13B···O9ⁱⁱ	0.96	2.41	3.211 (6)	141
C21—H21A···O5ⁱⁱⁱ	0.96	2.48	3.243 (5)	136
C24—H24A···O9^iv	0.97	2.59	3.276 (6)	128

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, y−1/2, −z+3/2; (iii) x, y, z+1; (iv) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₄ClNO₆
M_r	303.69
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	23.150 (5), 15.013 (3), 8.0700 (16)
β (°)	93.42 (3)
V (Å³)	2799.7 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.916, 0.943
No. of measured, independent and observed [I > 2σ(I)] reflections	5208, 5096, 2874
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.162, 1.03
No. of reflections	5096
No. of parameters	362
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.30

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O4ⁱ	0.97	2.58	3.336 (7)	135
C13—H13B···O9ⁱⁱ	0.96	2.41	3.211 (6)	141
C21—H21A···O5ⁱⁱⁱ	0.96	2.48	3.243 (5)	136
C24—H24A···O9^iv	0.97	2.59	3.276 (6)	128

Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, y−1/2, −z+3/2; (iii) x, y, z+1; (iv) −x+1, −y+1, −z+1.

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
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft. The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Knesl, P., Roeseling, D. & Jordis, U. (2006). Molecules, 11, 286–297. Web of Science CrossRef PubMed CAS Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science 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 65| Part 4| April 2009| Page o781

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