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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2426.
Published online 2008 November 22. doi:  10.1107/S1600536808038555
PMCID: PMC2959909

N-Benzyl-2-(2-chloro-5-methyl­phen­oxy)acetamide

Abstract

The asymmetric unit of the title compound, C16H16ClNO2, contains two crystallographically independent mol­ecules, which differ mainly in the orientation of the benzyl group with respect to the rest of the mol­ecule. In the crystal packing, centrosymmetrically related mol­ecules are linked into dimers via inter­molecular C—H(...)O hydrogen-bond inter­actions.

Related literature

For a related structure, see: Li et al. (2008 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]).

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Object name is e-64-o2426-scheme1.jpg

Experimental

Crystal data

  • C16H16ClNO2
  • M r = 289.75
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2426-efi1.jpg
  • a = 9.5549 (18) Å
  • b = 11.086 (2) Å
  • c = 14.725 (3) Å
  • α = 71.747 (4)°
  • β = 89.062 (4)°
  • γ = 85.655 (4)°
  • V = 1477.0 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.26 mm−1
  • T = 298 (2) K
  • 0.12 × 0.10 × 0.06 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.970, T max = 0.985
  • 7851 measured reflections
  • 5194 independent reflections
  • 2351 reflections with I > 2σ(I)
  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.153
  • S = 0.98
  • 5194 reflections
  • 362 parameters
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: XP in SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808038555/rz2267sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038555/rz2267Isup2.hkl

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

Acknowledgments

This study was supported by the Key Program Projects of the Municipal Natural Science Foundation of Chongqing, China (grant No. CSTC, 2008 A A1001).

supplementary crystallographic information

Comment

As part of our continuing project on the study of the interactions occurring between small molecules and proteins (Li et al.; 2008), we report here the synthesis and crystal structure of the title compound.

The asymmetric unit of the title compound (Fig. 1) contains two crystallographically independent molecules which differ mainly in the orientation of the benzyl groups (C10—C15 and C26—C32) bound to the amidic N atoms with respect of the mean plane through the rest of the molecule (dihedral angles of 87.03 (8) and 68.74 (6)° respectively). The O1—C8—C9—O2 and O3—C24—C25—O4 torsion angles are -176.5 (3) and -179.0 (3)°, respectively. These values can be compared with that of 10.5 (3)° found in the similar dichloro compound (Li et al.; 2008). In the crystal structure, centrosymmetrically related molecules are linked into dimers by intermolecular C—H···O hydrogen bonds (Table 1), forming fourteen-membered rings of graph set motif R22(14) (Bernstein et al., 1995).

Experimental

A solution of 2-chloro-5-methylphenol (1.0 mmol), N-benzyl-2-chloroacetamide (1.1 mmol), K2CO3 (1.1 mmol) and CH3CN (20 ml) was refluxed for 3 h. After completion of the reaction (by TLC monitoring), the solution was cooled and the solvent was evaporated under reduced pressure. The residue was poured into water and adjusted to pH 6–7 with dilute hydrochloric acid (10%) and extracted with ethyl acetate, washed with brine and dried over anhydrous MgSO4. The mixture was then filtered and the filtrate obtained was concentrated under reduced pressure to obtain the corresponding crude product. The product was purified by column chromatography on silica gel using ethyl acetate as eluent (yield 86%). Crystals suitable for X-ray diffraction were obtained by slow evaparation of an ethyl acetate/hexane (1:1 v/v) solution at room temperature for 10 days.

Refinement

All H atoms were placed in calculated positions and refined as riding, with C—H = 0.93-0.97 Å, N—H = 0.86 Å and with Uiso(H) = 1.2Ueq(C, N) or 1.5Ueq(C) for methyl H atoms.

Figures

Fig. 1.
The molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level for non-H atoms.

Crystal data

C16H16ClNO2Z = 4
Mr = 289.75F000 = 608
Triclinic, P1Dx = 1.303 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 9.5549 (18) ÅCell parameters from 818 reflections
b = 11.086 (2) Åθ = 5.5–38.5º
c = 14.725 (3) ŵ = 0.26 mm1
α = 71.747 (4)ºT = 298 (2) K
β = 89.062 (4)ºBlock, colourless
γ = 85.655 (4)º0.12 × 0.10 × 0.06 mm
V = 1477.0 (5) Å3

Data collection

Bruker SMART CCD area-detector diffractometer5194 independent reflections
Radiation source: fine-focus sealed tube2351 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.033
T = 298(2) Kθmax = 25.1º
[var phi] and ω scansθmin = 1.5º
Absorption correction: multi-scan(SADABS; Bruker, 2005)h = −11→11
Tmin = 0.970, Tmax = 0.985k = −12→13
7851 measured reflectionsl = −14→17

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.054  w = 1/[σ2(Fo2) + (0.0578P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.153(Δ/σ)max < 0.001
S = 0.98Δρmax = 0.18 e Å3
5194 reflectionsΔρmin = −0.23 e Å3
362 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0039 (10)
Secondary atom site location: difference Fourier map

Special details

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)

xyzUiso*/Ueq
Cl10.96319 (12)0.34345 (9)0.13691 (6)0.0838 (4)
Cl20.50957 (12)0.36619 (10)0.12091 (6)0.0843 (4)
O10.8583 (2)0.1676 (2)0.30620 (15)0.0613 (7)
O20.6330 (3)−0.0799 (2)0.39861 (18)0.0816 (8)
O30.3863 (2)0.1968 (2)0.28614 (14)0.0612 (7)
O40.1458 (3)−0.0409 (2)0.37055 (17)0.0717 (8)
N10.6903 (3)0.0326 (3)0.2484 (2)0.0632 (8)
H10.74060.09090.21390.076*
N20.2154 (3)0.0694 (2)0.22282 (19)0.0562 (8)
H20.27220.12310.19050.067*
C11.0023 (4)0.3375 (3)0.2529 (2)0.0595 (10)
C20.9435 (3)0.2484 (3)0.3297 (2)0.0513 (9)
C30.9725 (3)0.2452 (3)0.4215 (2)0.0558 (9)
H30.93330.18510.47260.067*
C41.0594 (4)0.3303 (4)0.4391 (3)0.0622 (10)
C51.1172 (4)0.4175 (4)0.3616 (3)0.0755 (12)
H51.17630.47490.37200.091*
C61.0892 (4)0.4211 (3)0.2698 (3)0.0739 (11)
H61.12930.48050.21870.089*
C71.0907 (4)0.3245 (4)0.5403 (3)0.0881 (13)
H7A1.01740.28410.58140.132*
H7B1.09590.40930.54330.132*
H7C1.17870.27630.56050.132*
C80.7986 (3)0.0726 (3)0.3822 (2)0.0582 (10)
H8A0.74840.11210.42460.070*
H8B0.87260.01350.41890.070*
C90.6998 (4)0.0018 (3)0.3432 (3)0.0553 (9)
C100.5997 (4)−0.0276 (4)0.2010 (3)0.0732 (11)
H10A0.54850.03790.15040.088*
H10B0.5316−0.07150.24660.088*
C110.6762 (4)−0.1216 (3)0.1586 (2)0.0555 (9)
C120.8057 (4)−0.1810 (4)0.1908 (3)0.0680 (11)
H120.8494−0.16330.24070.082*
C130.8722 (5)−0.2667 (4)0.1503 (4)0.0905 (14)
H130.9598−0.30590.17310.109*
C140.8103 (7)−0.2939 (5)0.0774 (4)0.1025 (17)
H140.8551−0.35110.04980.123*
C150.6804 (7)−0.2356 (5)0.0448 (3)0.0996 (17)
H150.6371−0.2539−0.00490.119*
C160.6137 (4)−0.1502 (4)0.0853 (3)0.0738 (12)
H160.5257−0.11180.06270.089*
C170.5350 (4)0.3631 (3)0.2384 (2)0.0540 (9)
C180.4702 (3)0.2756 (3)0.3119 (2)0.0496 (9)
C190.4939 (3)0.2724 (3)0.4050 (2)0.0540 (9)
H190.45030.21410.45490.065*
C200.5820 (4)0.3550 (3)0.4249 (2)0.0556 (9)
C210.6439 (4)0.4419 (3)0.3503 (3)0.0657 (10)
H210.70200.49860.36270.079*
C220.6209 (4)0.4461 (3)0.2575 (3)0.0663 (10)
H220.66360.50520.20760.080*
C230.6128 (4)0.3443 (4)0.5272 (2)0.0848 (13)
H23A0.70200.29760.54620.127*
H23B0.54070.30050.56770.127*
H23C0.61550.42800.53300.127*
C240.3147 (3)0.1067 (3)0.3610 (2)0.0556 (9)
H24A0.26130.15070.39930.067*
H24B0.38260.04540.40240.067*
C250.2180 (4)0.0391 (3)0.3175 (3)0.0551 (9)
C260.1215 (4)0.0163 (3)0.1709 (2)0.0634 (10)
H26A0.08990.08240.11280.076*
H26B0.0395−0.01000.20980.076*
C270.1878 (3)−0.0956 (3)0.1448 (2)0.0514 (9)
C280.1796 (4)−0.1007 (4)0.0525 (3)0.0666 (11)
H280.1372−0.03150.00520.080*
C290.2332 (5)−0.2062 (5)0.0292 (3)0.0821 (13)
H290.2261−0.2079−0.03330.099*
C300.2966 (5)−0.3083 (4)0.0978 (4)0.0830 (13)
H300.3314−0.38000.08240.100*
C310.3087 (4)−0.3043 (4)0.1899 (3)0.0763 (12)
H310.3548−0.37210.23630.092*
C320.2528 (4)−0.2002 (4)0.2128 (3)0.0654 (10)
H320.2586−0.19980.27570.078*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.1148 (9)0.0760 (7)0.0597 (6)−0.0167 (6)0.0051 (6)−0.0180 (5)
Cl20.1155 (9)0.0892 (8)0.0509 (6)−0.0252 (7)0.0039 (6)−0.0218 (5)
O10.0719 (17)0.0588 (15)0.0535 (14)−0.0184 (14)0.0021 (13)−0.0150 (12)
O20.082 (2)0.0840 (19)0.0773 (18)−0.0361 (17)0.0169 (15)−0.0170 (15)
O30.0689 (16)0.0691 (16)0.0527 (14)−0.0265 (14)0.0068 (12)−0.0246 (12)
O40.0743 (18)0.0733 (17)0.0716 (17)−0.0294 (15)0.0172 (14)−0.0235 (14)
N10.062 (2)0.072 (2)0.060 (2)−0.0189 (17)0.0046 (16)−0.0251 (16)
N20.0544 (19)0.0574 (19)0.0608 (19)−0.0111 (15)0.0006 (15)−0.0224 (15)
C10.070 (3)0.055 (2)0.056 (2)−0.006 (2)0.007 (2)−0.0213 (19)
C20.048 (2)0.045 (2)0.062 (2)0.0001 (18)−0.0048 (19)−0.0204 (18)
C30.058 (2)0.053 (2)0.059 (2)0.0026 (19)−0.0026 (19)−0.0226 (18)
C40.062 (3)0.059 (2)0.074 (3)0.004 (2)−0.008 (2)−0.033 (2)
C50.082 (3)0.061 (3)0.095 (3)−0.016 (2)−0.008 (3)−0.039 (2)
C60.082 (3)0.056 (3)0.086 (3)−0.016 (2)0.005 (2)−0.023 (2)
C70.100 (3)0.086 (3)0.091 (3)0.003 (3)−0.027 (3)−0.047 (2)
C80.059 (2)0.058 (2)0.057 (2)−0.008 (2)0.0072 (19)−0.0167 (18)
C90.048 (2)0.057 (2)0.062 (2)−0.0025 (19)0.002 (2)−0.0193 (19)
C100.061 (3)0.084 (3)0.081 (3)−0.009 (2)−0.010 (2)−0.034 (2)
C110.053 (2)0.063 (2)0.051 (2)−0.017 (2)−0.0016 (19)−0.0167 (18)
C120.058 (3)0.073 (3)0.074 (3)−0.012 (2)0.000 (2)−0.024 (2)
C130.082 (3)0.068 (3)0.125 (4)−0.012 (3)0.017 (3)−0.035 (3)
C140.130 (5)0.082 (4)0.113 (4)−0.041 (4)0.055 (4)−0.051 (3)
C150.150 (5)0.094 (4)0.074 (3)−0.054 (4)0.016 (4)−0.044 (3)
C160.082 (3)0.078 (3)0.062 (2)−0.027 (2)−0.011 (2)−0.017 (2)
C170.059 (2)0.055 (2)0.049 (2)−0.0040 (19)0.0014 (18)−0.0158 (18)
C180.046 (2)0.052 (2)0.056 (2)−0.0069 (18)−0.0008 (18)−0.0223 (18)
C190.057 (2)0.056 (2)0.050 (2)−0.0069 (19)0.0021 (18)−0.0176 (17)
C200.061 (2)0.054 (2)0.056 (2)−0.001 (2)−0.0069 (19)−0.0225 (18)
C210.069 (3)0.065 (3)0.072 (3)−0.015 (2)−0.007 (2)−0.031 (2)
C220.072 (3)0.058 (2)0.069 (3)−0.013 (2)0.009 (2)−0.019 (2)
C230.098 (3)0.089 (3)0.074 (3)−0.005 (3)−0.020 (2)−0.034 (2)
C240.056 (2)0.063 (2)0.051 (2)−0.0128 (19)0.0041 (18)−0.0208 (18)
C250.056 (2)0.055 (2)0.060 (2)−0.003 (2)0.008 (2)−0.0263 (19)
C260.057 (2)0.067 (3)0.070 (2)−0.004 (2)−0.011 (2)−0.027 (2)
C270.048 (2)0.058 (2)0.051 (2)−0.0118 (19)0.0000 (18)−0.0193 (19)
C280.066 (3)0.080 (3)0.056 (2)−0.021 (2)0.000 (2)−0.021 (2)
C290.092 (3)0.105 (4)0.066 (3)−0.039 (3)0.020 (3)−0.044 (3)
C300.089 (3)0.070 (3)0.104 (4)−0.028 (3)0.034 (3)−0.045 (3)
C310.085 (3)0.055 (3)0.086 (3)−0.003 (2)0.009 (3)−0.018 (2)
C320.075 (3)0.063 (3)0.059 (2)−0.007 (2)0.000 (2)−0.020 (2)

Geometric parameters (Å, °)

Cl1—C11.735 (3)C13—C141.357 (6)
Cl2—C171.741 (3)C13—H130.9300
O1—C21.378 (3)C14—C151.376 (6)
O1—C81.421 (3)C14—H140.9300
O2—C91.225 (4)C15—C161.380 (6)
O3—C181.369 (3)C15—H150.9300
O3—C241.439 (3)C16—H160.9300
O4—C251.231 (4)C17—C221.372 (4)
N1—C91.332 (4)C17—C181.381 (4)
N1—C101.442 (4)C18—C191.381 (4)
N1—H10.8600C19—C201.389 (4)
N2—C251.328 (4)C19—H190.9300
N2—C261.456 (4)C20—C211.373 (4)
N2—H20.8600C20—C231.506 (4)
C1—C61.370 (5)C21—C221.373 (4)
C1—C21.391 (4)C21—H210.9300
C2—C31.373 (4)C22—H220.9300
C3—C41.388 (4)C23—H23A0.9600
C3—H30.9300C23—H23B0.9600
C4—C51.383 (5)C23—H23C0.9600
C4—C71.504 (5)C24—C251.500 (4)
C5—C61.371 (5)C24—H24A0.9700
C5—H50.9300C24—H24B0.9700
C6—H60.9300C26—C271.504 (4)
C7—H7A0.9600C26—H26A0.9700
C7—H7B0.9600C26—H26B0.9700
C7—H7C0.9600C27—C281.382 (4)
C8—C91.500 (4)C27—C321.384 (4)
C8—H8A0.9700C28—C291.380 (5)
C8—H8B0.9700C28—H280.9300
C10—C111.513 (5)C29—C301.367 (6)
C10—H10A0.9700C29—H290.9300
C10—H10B0.9700C30—C311.377 (5)
C11—C161.374 (4)C30—H300.9300
C11—C121.375 (5)C31—C321.370 (5)
C12—C131.384 (5)C31—H310.9300
C12—H120.9300C32—H320.9300
C2—O1—C8117.8 (2)C16—C15—H15119.7
C18—O3—C24117.7 (2)C11—C16—C15120.5 (4)
C9—N1—C10122.9 (3)C11—C16—H16119.7
C9—N1—H1118.5C15—C16—H16119.7
C10—N1—H1118.5C22—C17—C18120.5 (3)
C25—N2—C26123.5 (3)C22—C17—Cl2119.8 (3)
C25—N2—H2118.3C18—C17—Cl2119.7 (3)
C26—N2—H2118.3O3—C18—C19124.6 (3)
C6—C1—C2119.5 (3)O3—C18—C17116.4 (3)
C6—C1—Cl1120.6 (3)C19—C18—C17119.0 (3)
C2—C1—Cl1119.9 (3)C18—C19—C20120.8 (3)
C3—C2—O1124.6 (3)C18—C19—H19119.6
C3—C2—C1119.9 (3)C20—C19—H19119.6
O1—C2—C1115.6 (3)C21—C20—C19118.9 (3)
C2—C3—C4121.0 (3)C21—C20—C23121.3 (3)
C2—C3—H3119.5C19—C20—C23119.7 (3)
C4—C3—H3119.5C22—C21—C20120.8 (3)
C5—C4—C3118.1 (3)C22—C21—H21119.6
C5—C4—C7121.8 (3)C20—C21—H21119.6
C3—C4—C7120.1 (3)C17—C22—C21120.0 (3)
C6—C5—C4121.3 (3)C17—C22—H22120.0
C6—C5—H5119.3C21—C22—H22120.0
C4—C5—H5119.3C20—C23—H23A109.5
C1—C6—C5120.2 (3)C20—C23—H23B109.5
C1—C6—H6119.9H23A—C23—H23B109.5
C5—C6—H6119.9C20—C23—H23C109.5
C4—C7—H7A109.5H23A—C23—H23C109.5
C4—C7—H7B109.5H23B—C23—H23C109.5
H7A—C7—H7B109.5O3—C24—C25109.4 (3)
C4—C7—H7C109.5O3—C24—H24A109.8
H7A—C7—H7C109.5C25—C24—H24A109.8
H7B—C7—H7C109.5O3—C24—H24B109.8
O1—C8—C9110.1 (3)C25—C24—H24B109.8
O1—C8—H8A109.6H24A—C24—H24B108.3
C9—C8—H8A109.6O4—C25—N2123.4 (3)
O1—C8—H8B109.6O4—C25—C24118.9 (3)
C9—C8—H8B109.6N2—C25—C24117.7 (3)
H8A—C8—H8B108.1N2—C26—C27113.6 (3)
O2—C9—N1123.7 (3)N2—C26—H26A108.9
O2—C9—C8119.4 (3)C27—C26—H26A108.9
N1—C9—C8116.9 (3)N2—C26—H26B108.9
N1—C10—C11114.0 (3)C27—C26—H26B108.9
N1—C10—H10A108.7H26A—C26—H26B107.7
C11—C10—H10A108.7C28—C27—C32117.4 (3)
N1—C10—H10B108.7C28—C27—C26120.9 (3)
C11—C10—H10B108.7C32—C27—C26121.7 (3)
H10A—C10—H10B107.6C29—C28—C27121.3 (4)
C16—C11—C12118.2 (4)C29—C28—H28119.4
C16—C11—C10119.0 (4)C27—C28—H28119.4
C12—C11—C10122.8 (3)C30—C29—C28120.1 (4)
C11—C12—C13121.1 (4)C30—C29—H29120.0
C11—C12—H12119.5C28—C29—H29120.0
C13—C12—H12119.5C29—C30—C31119.6 (4)
C14—C13—C12120.4 (5)C29—C30—H30120.2
C14—C13—H13119.8C31—C30—H30120.2
C12—C13—H13119.8C32—C31—C30119.8 (4)
C13—C14—C15119.1 (5)C32—C31—H31120.1
C13—C14—H14120.4C30—C31—H31120.1
C15—C14—H14120.4C31—C32—C27121.7 (4)
C14—C15—C16120.7 (5)C31—C32—H32119.1
C14—C15—H15119.7C27—C32—H32119.1
C8—O1—C2—C3−1.4 (5)C24—O3—C18—C191.8 (5)
C8—O1—C2—C1178.4 (3)C24—O3—C18—C17−178.5 (3)
C6—C1—C2—C30.2 (5)C22—C17—C18—O3179.9 (3)
Cl1—C1—C2—C3−178.8 (3)Cl2—C17—C18—O3−1.1 (4)
C6—C1—C2—O1−179.6 (3)C22—C17—C18—C19−0.4 (5)
Cl1—C1—C2—O11.4 (4)Cl2—C17—C18—C19178.5 (3)
O1—C2—C3—C4−179.9 (3)O3—C18—C19—C20179.2 (3)
C1—C2—C3—C40.4 (5)C17—C18—C19—C20−0.4 (5)
C2—C3—C4—C5−0.7 (5)C18—C19—C20—C211.1 (5)
C2—C3—C4—C7−179.5 (3)C18—C19—C20—C23−176.4 (3)
C3—C4—C5—C60.5 (6)C19—C20—C21—C22−1.0 (5)
C7—C4—C5—C6179.3 (4)C23—C20—C21—C22176.4 (4)
C2—C1—C6—C5−0.4 (6)C18—C17—C22—C210.5 (6)
Cl1—C1—C6—C5178.6 (3)Cl2—C17—C22—C21−178.5 (3)
C4—C5—C6—C10.0 (6)C20—C21—C22—C170.2 (6)
C2—O1—C8—C9175.0 (3)C18—O3—C24—C25174.4 (3)
C10—N1—C9—O20.1 (6)C26—N2—C25—O43.4 (5)
C10—N1—C9—C8180.0 (3)C26—N2—C25—C24−176.7 (3)
O1—C8—C9—O2−176.5 (3)O3—C24—C25—O4−179.0 (3)
O1—C8—C9—N13.6 (4)O3—C24—C25—N21.1 (4)
C9—N1—C10—C11−105.2 (4)C25—N2—C26—C27−96.3 (4)
N1—C10—C11—C16−157.2 (3)N2—C26—C27—C28−130.2 (3)
N1—C10—C11—C1223.4 (5)N2—C26—C27—C3253.2 (4)
C16—C11—C12—C130.4 (5)C32—C27—C28—C290.5 (5)
C10—C11—C12—C13179.9 (3)C26—C27—C28—C29−176.2 (3)
C11—C12—C13—C140.0 (6)C27—C28—C29—C30−0.4 (6)
C12—C13—C14—C15−0.4 (7)C28—C29—C30—C31−1.0 (6)
C13—C14—C15—C160.2 (7)C29—C30—C31—C322.3 (6)
C12—C11—C16—C15−0.6 (5)C30—C31—C32—C27−2.3 (6)
C10—C11—C16—C15180.0 (3)C28—C27—C32—C310.9 (5)
C14—C15—C16—C110.2 (6)C26—C27—C32—C31177.5 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3—H3···O4i0.932.513.423 (4)169
C19—H19···O2i0.932.373.287 (4)169

Symmetry codes: (i) −x+1, −y, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2267).

References

  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Bruker (2005). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Li, Z.-B., Luo, Y.-H., Dong, W.-L., Li, J. & Zuo, H. (2008). Acta Cryst. E64, o1610. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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