supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

Acta Cryst. (2009). E65, o781    [ doi:10.1107/S1600536809009076 ]

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

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

Abstract top

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.

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.

Refinement top

H atoms were positioned geometrically, with C-H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

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
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme.
[Figure 2] 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
C12H14ClNO6F(000) = 1264
Mr = 303.69Dx = 1.441 Mg m−3
Monoclinic, P21/cMelting point: 337 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 23.150 (5) ÅCell parameters from 25 reflections
b = 15.013 (3) Åθ = 10–13°
c = 8.0700 (16) ŵ = 0.30 mm−1
β = 93.42 (3)°T = 294 K
V = 2799.7 (10) Å3Needle, yellow
Z = 80.30 × 0.20 × 0.20 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer		2874 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.038
graphiteθmax = 25.3°, θmin = 1.6°
ω/2θ scansh = 0→27
Absorption correction: ψ scan
(North et al., 1968)		k = 0→18
Tmin = 0.916, Tmax = 0.943l = −9→9
5208 measured reflections3 standard reflections every 120 min
5096 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.065H-atom parameters constrained
wR(F2) = 0.162 w = 1/[σ2(Fo2) + (0.0567P)2 + 1.915P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
5096 reflectionsΔρmax = 0.40 e Å−3
362 parametersΔρmin = −0.30 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0049 (6)
Crystal data top
C12H14ClNO6V = 2799.7 (10) Å3
Mr = 303.69Z = 8
Monoclinic, P21/cMo Kα radiation
a = 23.150 (5) ŵ = 0.30 mm−1
b = 15.013 (3) ÅT = 294 K
c = 8.0700 (16) Å0.30 × 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)		Rint = 0.038
Tmin = 0.916, Tmax = 0.943θmax = 25.3°
5208 measured reflections3 standard reflections every 120 min
5096 independent reflections intensity decay: 1%
Refinement top
R[F2 > 2σ(F2)] = 0.065H-atom parameters constrained
wR(F2) = 0.162Δρmax = 0.40 e Å−3
S = 1.03Δρmin = −0.30 e Å−3
5096 reflectionsAbsolute structure: ?
362 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
xyzUiso*/Ueq
Cl10.26534 (6)0.48992 (8)0.29390 (17)0.0758 (4)
Cl20.30461 (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)
O50.13459 (12)0.23218 (18)0.0445 (4)0.0559 (8)
O60.14060 (12)0.40304 (18)0.0445 (4)0.0593 (8)
O70.40610 (12)0.06586 (17)0.5910 (4)0.0558 (8)
O80.48185 (14)0.1024 (2)0.7607 (4)0.0740 (10)
O90.53876 (12)0.3392 (2)0.6019 (4)0.0637 (9)
O100.51561 (13)0.2122 (2)0.4944 (4)0.0694 (9)
O110.28231 (11)0.33078 (17)0.7787 (4)0.0528 (7)
O120.34201 (12)0.46634 (17)0.7009 (4)0.0538 (8)
N1−0.04080 (17)0.4270 (3)0.3109 (6)0.0687 (11)
N20.50447 (14)0.2793 (2)0.5715 (4)0.0466 (8)
C1−0.1592 (2)0.2271 (5)0.2275 (9)0.124 (3)
H1A−0.19070.26070.17610.185*
H1B−0.16350.22370.34490.185*
H1C−0.15930.16810.18160.185*
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)
C40.00118 (18)0.3722 (3)0.2282 (5)0.0495 (10)
C50.04788 (18)0.4163 (3)0.1691 (5)0.0542 (11)
H5A0.04980.47810.17240.065*
C60.09190 (17)0.3675 (3)0.1046 (5)0.0474 (10)
C70.08873 (17)0.2742 (3)0.1040 (5)0.0463 (10)
C80.04040 (17)0.2321 (3)0.1598 (5)0.0476 (10)
H8A0.03800.17020.15640.057*
C90.1376 (2)0.1372 (3)0.0606 (6)0.0626 (12)
H9A0.17210.11590.01330.094*
H9B0.10430.11090.00330.094*
H9C0.13840.12130.17590.094*
C100.1491 (2)0.4975 (3)0.0631 (7)0.0645 (13)
H10A0.14940.51400.17940.077*
H10B0.11820.52970.00310.077*
C110.2060 (2)0.5190 (3)−0.0057 (6)0.0638 (13)
H11A0.21280.58250.00570.077*
H11B0.20370.5053−0.12340.077*
C120.25688 (19)0.4705 (3)0.0750 (6)0.0612 (12)
H12A0.29180.48930.02410.073*
H12B0.25210.40710.05530.073*
C130.4229 (2)−0.0264 (3)0.6021 (7)0.0748 (15)
H13A0.3962−0.06170.53440.112*
H13B0.4226−0.04580.71540.112*
H13C0.4611−0.03320.56380.112*
C140.43940 (17)0.1222 (3)0.6788 (5)0.0433 (10)
C150.41457 (15)0.2145 (2)0.6687 (4)0.0367 (9)
C160.35887 (16)0.2280 (2)0.7183 (5)0.0409 (9)
H16A0.33650.17900.74420.049*
C170.33587 (16)0.3122 (2)0.7300 (5)0.0397 (9)
C180.36847 (16)0.3871 (2)0.6871 (5)0.0415 (9)
C190.42370 (16)0.3744 (2)0.6376 (5)0.0418 (9)
H19A0.44600.42310.60980.050*
C200.44601 (15)0.2890 (2)0.6293 (4)0.0378 (9)
C210.24745 (17)0.2586 (3)0.8302 (5)0.0521 (11)
H21A0.21080.28110.86130.078*
H21B0.26670.22920.92350.078*
H21C0.24140.21710.74040.078*
C220.3705 (2)0.5435 (3)0.6460 (6)0.0567 (11)
H22A0.37810.53840.52950.068*
H22B0.40700.55230.70960.068*
C230.3290 (2)0.6207 (3)0.6738 (7)0.0680 (14)
H23A0.29310.61080.60800.082*
H23B0.32010.62220.78970.082*
C240.3531 (2)0.7046 (3)0.6292 (8)0.0895 (18)
H24A0.36290.70240.51410.107*
H24B0.38850.71490.69690.107*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0858 (9)0.0698 (8)0.0709 (8)−0.0107 (7)−0.0018 (7)−0.0109 (7)
Cl20.0811 (9)0.0518 (7)0.1376 (13)0.0225 (6)0.0417 (9)0.0179 (8)
O10.049 (2)0.095 (3)0.111 (3)−0.0011 (18)0.0157 (19)0.046 (2)
O20.071 (2)0.066 (2)0.079 (2)−0.0029 (17)0.0184 (18)0.0170 (19)
O30.124 (3)0.119 (3)0.087 (3)0.048 (3)0.053 (3)0.017 (3)
O40.088 (3)0.059 (2)0.148 (4)0.018 (2)0.037 (2)0.006 (2)
O50.0529 (18)0.0488 (17)0.068 (2)−0.0020 (14)0.0179 (15)−0.0026 (15)
O60.0515 (18)0.0475 (17)0.080 (2)−0.0126 (14)0.0128 (16)−0.0039 (15)
O70.0585 (18)0.0382 (15)0.069 (2)0.0053 (14)−0.0072 (15)−0.0044 (15)
O80.064 (2)0.064 (2)0.089 (2)0.0219 (17)−0.0301 (19)−0.0083 (18)
O90.0436 (17)0.071 (2)0.078 (2)−0.0114 (16)0.0142 (15)−0.0192 (17)
O100.062 (2)0.060 (2)0.089 (2)0.0059 (16)0.0290 (18)−0.0250 (18)
O110.0425 (16)0.0458 (16)0.072 (2)0.0063 (13)0.0190 (14)−0.0015 (15)
O120.0547 (18)0.0370 (15)0.072 (2)0.0082 (13)0.0231 (15)0.0010 (14)
N10.062 (3)0.070 (3)0.075 (3)0.008 (2)0.011 (2)0.000 (2)
N20.041 (2)0.051 (2)0.049 (2)0.0044 (17)0.0083 (16)−0.0039 (18)
C10.048 (3)0.155 (6)0.171 (7)−0.014 (4)0.023 (4)0.067 (5)
C20.048 (3)0.068 (3)0.052 (3)0.001 (2)0.014 (2)0.001 (2)
C30.044 (2)0.056 (3)0.043 (2)0.004 (2)0.0049 (19)0.001 (2)
C40.046 (2)0.055 (3)0.048 (3)0.005 (2)0.005 (2)−0.008 (2)
C50.052 (3)0.045 (2)0.065 (3)−0.001 (2)−0.003 (2)−0.003 (2)
C60.043 (2)0.051 (3)0.048 (3)−0.005 (2)0.000 (2)−0.001 (2)
C70.048 (3)0.046 (2)0.044 (2)−0.002 (2)0.000 (2)−0.006 (2)
C80.050 (3)0.044 (2)0.049 (3)−0.005 (2)0.006 (2)0.001 (2)
C90.063 (3)0.049 (3)0.078 (3)−0.001 (2)0.017 (2)−0.006 (2)
C100.060 (3)0.042 (2)0.092 (4)−0.007 (2)0.002 (3)0.003 (2)
C110.073 (3)0.047 (3)0.071 (3)−0.014 (2)0.004 (3)0.005 (2)
C120.058 (3)0.059 (3)0.067 (3)−0.009 (2)0.013 (2)−0.007 (2)
C130.082 (4)0.036 (2)0.106 (4)0.005 (2)0.001 (3)0.000 (3)
C140.044 (2)0.046 (2)0.041 (2)0.004 (2)0.0054 (19)−0.0019 (19)
C150.038 (2)0.039 (2)0.033 (2)0.0017 (17)0.0013 (17)−0.0016 (17)
C160.041 (2)0.036 (2)0.046 (2)−0.0013 (17)0.0048 (18)0.0002 (18)
C170.036 (2)0.044 (2)0.040 (2)0.0053 (18)0.0084 (17)−0.0025 (18)
C180.046 (2)0.039 (2)0.041 (2)0.0089 (19)0.0060 (18)−0.0043 (18)
C190.049 (2)0.039 (2)0.039 (2)−0.0025 (18)0.0081 (18)−0.0030 (18)
C200.035 (2)0.044 (2)0.035 (2)0.0052 (17)0.0059 (16)−0.0034 (17)
C210.046 (2)0.058 (3)0.053 (3)−0.004 (2)0.013 (2)−0.004 (2)
C220.068 (3)0.040 (2)0.063 (3)0.007 (2)0.016 (2)0.001 (2)
C230.074 (3)0.046 (3)0.087 (4)0.006 (2)0.030 (3)−0.001 (3)
C240.080 (4)0.061 (3)0.131 (5)0.013 (3)0.036 (4)−0.002 (3)
Geometric parameters (Å, °) top
Cl1—C121.789 (5)C9—H9A0.9600
Cl2—C241.778 (5)C9—H9B0.9600
O1—C21.345 (5)C9—H9C0.9600
O1—C11.439 (5)C10—C111.496 (6)
O2—C21.187 (5)C10—H10A0.9700
O3—N11.208 (5)C10—H10B0.9700
O4—N11.218 (5)C11—C121.500 (6)
O5—C71.348 (5)C11—H11A0.9700
O5—C91.433 (5)C11—H11B0.9700
O6—C61.363 (4)C12—H12A0.9700
O6—C101.438 (5)C12—H12B0.9700
O7—C141.322 (5)C13—H13A0.9600
O7—C131.440 (5)C13—H13B0.9600
O8—C141.189 (4)C13—H13C0.9600
O9—N21.215 (4)C14—C151.501 (5)
O10—N21.220 (4)C15—C201.382 (5)
O11—C171.352 (4)C15—C161.388 (5)
O11—C211.427 (4)C16—C171.377 (5)
O12—C181.346 (4)C16—H16A0.9300
O12—C221.417 (5)C17—C181.409 (5)
N1—C41.464 (5)C18—C191.375 (5)
N2—C201.465 (5)C19—C201.385 (5)
C1—H1A0.9600C19—H19A0.9300
C1—H1B0.9600C21—H21A0.9600
C1—H1C0.9600C21—H21B0.9600
C2—C31.493 (6)C21—H21C0.9600
C3—C41.372 (5)C22—C231.530 (5)
C3—C81.393 (5)C22—H22A0.9700
C4—C51.377 (6)C22—H22B0.9700
C5—C61.381 (5)C23—C241.432 (6)
C5—H5A0.9300C23—H23A0.9700
C6—C71.402 (5)C23—H23B0.9700
C7—C81.384 (5)C24—H24A0.9700
C8—H8A0.9300C24—H24B0.9700
C2—O1—C1115.8 (4)C11—C12—Cl1112.7 (3)
C7—O5—C9118.0 (3)C11—C12—H12A109.0
C6—O6—C10117.4 (3)Cl1—C12—H12A109.0
C14—O7—C13115.8 (3)C11—C12—H12B109.0
C17—O11—C21118.2 (3)Cl1—C12—H12B109.0
C18—O12—C22118.3 (3)H12A—C12—H12B107.8
O3—N1—O4124.0 (4)O7—C13—H13A109.5
O3—N1—C4118.3 (4)O7—C13—H13B109.5
O4—N1—C4117.6 (4)H13A—C13—H13B109.5
O9—N2—O10124.0 (3)O7—C13—H13C109.5
O9—N2—C20117.9 (3)H13A—C13—H13C109.5
O10—N2—C20118.2 (3)H13B—C13—H13C109.5
O1—C1—H1A109.5O8—C14—O7125.0 (4)
O1—C1—H1B109.5O8—C14—C15124.2 (4)
H1A—C1—H1B109.5O7—C14—C15110.7 (3)
O1—C1—H1C109.5C20—C15—C16117.3 (3)
H1A—C1—H1C109.5C20—C15—C14123.7 (3)
H1B—C1—H1C109.5C16—C15—C14118.6 (3)
O2—C2—O1123.7 (4)C17—C16—C15121.6 (3)
O2—C2—C3125.6 (4)C17—C16—H16A119.2
O1—C2—C3110.5 (4)C15—C16—H16A119.2
C4—C3—C8118.0 (4)O11—C17—C16125.1 (3)
C4—C3—C2125.8 (4)O11—C17—C18114.9 (3)
C8—C3—C2116.1 (4)C16—C17—C18120.0 (3)
C3—C4—C5122.7 (4)O12—C18—C19125.6 (4)
C3—C4—N1120.8 (4)O12—C18—C17115.6 (3)
C5—C4—N1116.4 (4)C19—C18—C17118.8 (3)
C4—C5—C6119.2 (4)C18—C19—C20119.8 (3)
C4—C5—H5A120.4C18—C19—H19A120.1
C6—C5—H5A120.4C20—C19—H19A120.1
O6—C6—C5124.9 (4)C15—C20—C19122.3 (3)
O6—C6—C7115.7 (4)C15—C20—N2120.1 (3)
C5—C6—C7119.4 (4)C19—C20—N2117.5 (3)
O5—C7—C8124.8 (4)O11—C21—H21A109.5
O5—C7—C6115.3 (3)O11—C21—H21B109.5
C8—C7—C6119.9 (4)H21A—C21—H21B109.5
C7—C8—C3120.6 (4)O11—C21—H21C109.5
C7—C8—H8A119.7H21A—C21—H21C109.5
C3—C8—H8A119.7H21B—C21—H21C109.5
O5—C9—H9A109.5O12—C22—C23105.3 (3)
O5—C9—H9B109.5O12—C22—H22A110.7
H9A—C9—H9B109.5C23—C22—H22A110.7
O5—C9—H9C109.5O12—C22—H22B110.7
H9A—C9—H9C109.5C23—C22—H22B110.7
H9B—C9—H9C109.5H22A—C22—H22B108.8
O6—C10—C11107.0 (4)C24—C23—C22111.8 (4)
O6—C10—H10A110.3C24—C23—H23A109.2
C11—C10—H10A110.3C22—C23—H23A109.2
O6—C10—H10B110.3C24—C23—H23B109.2
C11—C10—H10B110.3C22—C23—H23B109.2
H10A—C10—H10B108.6H23A—C23—H23B107.9
C10—C11—C12114.8 (4)C23—C24—Cl2112.4 (4)
C10—C11—H11A108.6C23—C24—H24A109.1
C12—C11—H11A108.6Cl2—C24—H24A109.1
C10—C11—H11B108.6C23—C24—H24B109.1
C12—C11—H11B108.6Cl2—C24—H24B109.1
H11A—C11—H11B107.5H24A—C24—H24B107.9
C1—O1—C2—O25.3 (7)C13—O7—C14—O81.8 (6)
C1—O1—C2—C3179.9 (5)C13—O7—C14—C15−175.1 (3)
O2—C2—C3—C4−143.1 (5)O8—C14—C15—C2053.4 (6)
O1—C2—C3—C442.5 (6)O7—C14—C15—C20−129.7 (4)
O2—C2—C3—C841.7 (6)O8—C14—C15—C16−119.6 (5)
O1—C2—C3—C8−132.8 (4)O7—C14—C15—C1657.4 (5)
C8—C3—C4—C53.9 (6)C20—C15—C16—C17−0.8 (5)
C2—C3—C4—C5−171.3 (4)C14—C15—C16—C17172.6 (4)
C8—C3—C4—N1−171.9 (4)C21—O11—C17—C163.3 (6)
C2—C3—C4—N112.9 (7)C21—O11—C17—C18−177.7 (3)
O3—N1—C4—C333.0 (7)C15—C16—C17—O11−179.4 (3)
O4—N1—C4—C3−147.6 (4)C15—C16—C17—C181.6 (6)
O3—N1—C4—C5−143.1 (5)C22—O12—C18—C196.2 (6)
O4—N1—C4—C536.3 (6)C22—O12—C18—C17−174.6 (4)
C3—C4—C5—C6−2.3 (7)O11—C17—C18—O120.2 (5)
N1—C4—C5—C6173.7 (4)C16—C17—C18—O12179.3 (3)
C10—O6—C6—C55.8 (6)O11—C17—C18—C19179.4 (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—C20179.7 (4)
C4—C5—C6—C7−1.4 (6)C17—C18—C19—C200.6 (6)
C9—O5—C7—C8−9.0 (6)C16—C15—C20—C19−0.2 (5)
C9—O5—C7—C6172.0 (4)C14—C15—C20—C19−173.2 (4)
O6—C6—C7—O50.3 (5)C16—C15—C20—N2−178.3 (3)
C5—C6—C7—O5−177.6 (4)C14—C15—C20—N28.7 (6)
O6—C6—C7—C8−178.8 (3)C18—C19—C20—C150.3 (6)
C5—C6—C7—C83.3 (6)C18—C19—C20—N2178.4 (3)
O5—C7—C8—C3179.3 (4)O9—N2—C20—C15−150.4 (4)
C6—C7—C8—C3−1.7 (6)O10—N2—C20—C1530.4 (5)
C4—C3—C8—C7−1.8 (6)O9—N2—C20—C1931.4 (5)
C2—C3—C8—C7173.8 (4)O10—N2—C20—C19−147.8 (4)
C6—O6—C10—C11177.8 (4)C18—O12—C22—C23178.5 (4)
O6—C10—C11—C12−58.2 (5)O12—C22—C23—C24177.8 (5)
C10—C11—C12—Cl1−57.8 (5)C22—C23—C24—Cl2178.6 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C10—H10B···O4i0.972.583.336 (7)135
C13—H13B···O9ii0.962.413.211 (6)141
C21—H21A···O5iii0.962.483.243 (5)136
C24—H24A···O9iv0.972.593.276 (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.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C10—H10B···O4i0.972.583.336 (7)135
C13—H13B···O9ii0.962.413.211 (6)141
C21—H21A···O5iii0.962.483.243 (5)136
C24—H24A···O9iv0.972.593.276 (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
References top

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.

Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft. The Netherlands.

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.

Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.

Knesl, P., Roeseling, D. & Jordis, U. (2006). Molecules, 11, 286–297.

North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.