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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o781.
Published online 2009 March 19. doi:  10.1107/S1600536809009076
PMCID: PMC2969097

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

Abstract

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 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

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Object name is e-65-0o781-scheme1.jpg

Experimental

Crystal data

  • C12H14ClNO6
  • M r = 303.69
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o781-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.065
  • wR(F 2) = 0.162
  • S = 1.03
  • 5096 reflections
  • 362 parameters
  • H-atom parameters constrained
  • Δρmax = 0.40 e Å−3
  • Δρmin = −0.30 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 [triangle]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

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.

Experimental

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

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.

Figures

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.

Crystal data

C12H14ClNO6F(000) = 1264
Mr = 303.69Dx = 1.441 Mg m3
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 mm1
β = 93.42 (3)°T = 294 K
V = 2799.7 (10) Å3Needle, yellow
Z = 80.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer2874 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

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) = 0.162w = 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 Å3
362 parametersΔρmin = −0.30 e Å3
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)

Special details

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)

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2642).

References

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