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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o2976.
Published online 2009 November 4. doi:  10.1107/S1600536809045553
PMCID: PMC2971953

3-(3-Chloro­phen­yl)-N-phenyl­oxirane-2-carboxamide

Abstract

There are two independent mol­ecules in the asymmetric unit of the title compound, C15H12ClN2O2. In each mol­ecule, the two benzene rings adopt a cis configuration with respect to the ep­oxy ring. The dihedral angles between the ep­oxy ring and chloro­phenyl rings are essentially identical in the two mol­ecules [62.50 (9) and 62.67 (9)°]. Inter­molecualar N—H(...)O and C—H(...)O hydrogen bonding is present in the crystal structure.

Related literature

For the use of epoxide-containing compounds as building blocks in the synthesis of a wide range of polyfunctional compounds, see: Imashiro & Seki (2004 [triangle]); Porter & Skidmore (2000 [triangle]); Shing et al. (2006 [triangle]); Zhu & Espenson (1995 [triangle]). For a related structure, see: He (2009 [triangle]).

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Object name is e-65-o2976-scheme1.jpg

Experimental

Crystal data

  • C15H12ClNO2
  • M r = 273.71
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2976-efi1.jpg
  • a = 5.4480 (1) Å
  • b = 11.1481 (2) Å
  • c = 21.3152 (4) Å
  • β = 94.472 (2)°
  • V = 1290.63 (4) Å3
  • Z = 4
  • Cu Kα radiation
  • μ = 2.60 mm−1
  • T = 295 K
  • 0.40 × 0.30 × 0.30 mm

Data collection

  • Oxford Diffraction Gemini S Ultra diffractometer
  • Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 [triangle]) T min = 0.423, T max = 0.510
  • 19148 measured reflections
  • 4775 independent reflections
  • 4453 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.028
  • wR(F 2) = 0.072
  • S = 1.00
  • 4775 reflections
  • 351 parameters
  • 3 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.32 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2223 Friedel pairs
  • Flack parameter: 0.000 (9)

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 [triangle]); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045553/xu2659sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045553/xu2659Isup2.hkl

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

Acknowledgments

The diffraction measurements were made at the Centre for Testing and Analysis, Sichuan university. We acknowledge financial support from China West Normal University.

supplementary crystallographic information

Comment

Epoxides are particularly versatile synthetic intermediates which can readily be converted into a wide range of polyfunctional compounds (Imashiro et al. 2004; Porter et al. 2000; Shing et al. 2006). A useful method for the synthesis of α, β-epoxy carbonyl compounds and related compounds is the Darzens condensation between a carbonyl compound and α-halo-carbonyl compound (Zhu et al. 1995). We report herein the crystal structure of the title compound.

The molecular structure of (I) is shown in Fig. 1. Bond lengths and angles in (I) are normal. The asymmetric unit of the title compound consists of two crystallographically independent molecules (Fig. 1) each of which adopts a cis configuration about the epoxides ring. The dihedral angle between the C1—C6 and C10—C15 ring is 82.14 (5)° and that between C16–21 and C25–30 phenyl ring is 84.15 (4)°. The dihedral angles between the epoxy ring and chlorophenyl rings are essentially identical for the two independent molecules [62.50 (9)° and 62.67 (9)°]. The crystal packing is stabilized by N—H···0 and C—H···0 hydrogen bonding (Table 1).

Experimental

2-Chloro-N-phenylacetamide (0.17 g, 1.0 mmol) and potassium hydroxide (0.112 g, 2.0 mmol) were dissolved in acetonitrile (2 ml). To the solution was added 3-chlorophenylaldehyde (0.15 g, 1.0 mmol) at 298 K, the solution was stirred for 60 min and removal of solvent under reduced pressure, the residue was purified through column chromatography. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution at room temperature for 2 d.

Refinement

H atoms on N atoms were located in a difference Fourier map and refined isotropically, with restrains of N—H = 0.89±0.01 Å. Other H atoms were positioned geometrically with C—H = 0.93 and 0.98 Å, for aromatic and methine H atoms, respectively, and refined using a riding model, with Uiso(H) =1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of (I) with 30% probability displacement ellipsoids (arbitrary spheres for H atoms).

Crystal data

C15H12ClNO2F(000) = 568
Mr = 273.71Dx = 1.409 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2ybCell parameters from 12871 reflections
a = 5.4480 (1) Åθ = 2.1–69.4°
b = 11.1481 (2) ŵ = 2.60 mm1
c = 21.3152 (4) ÅT = 295 K
β = 94.472 (2)°Block, colorless
V = 1290.63 (4) Å30.40 × 0.30 × 0.30 mm
Z = 4

Data collection

Oxford Diffraction Gemini S Ultra diffractometer4775 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source4453 reflections with I > 2σ(I)
mirrorRint = 0.030
Detector resolution: 15.9149 pixels mm-1θmax = 69.7°, θmin = 2.1°
ω scansh = −6→5
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)k = −13→13
Tmin = 0.423, Tmax = 0.510l = −25→25
19148 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.072w = 1/[σ2(Fo2) + (0.044P)2 + 0.0893P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
4775 reflectionsΔρmax = 0.16 e Å3
351 parametersΔρmin = −0.32 e Å3
3 restraintsAbsolute structure: Flack (1983), 2223 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.000 (9)

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
Cl20.94031 (10)0.56442 (6)0.21597 (3)0.07852 (18)
Cl10.50893 (11)0.28922 (5)0.71602 (3)0.07628 (16)
N21.1469 (2)0.78718 (12)−0.07435 (6)0.0417 (3)
O40.7412 (2)0.80333 (12)−0.05625 (5)0.0544 (3)
O31.2753 (2)0.95679 (10)0.01702 (6)0.0532 (3)
O20.7705 (2)0.71550 (11)0.52655 (6)0.0574 (3)
O10.2463 (2)0.56111 (12)0.44875 (5)0.0550 (3)
N10.6527 (2)0.55043 (12)0.43108 (6)0.0451 (3)
C60.5906 (3)0.47577 (15)0.63907 (7)0.0465 (4)
H60.45430.51150.65500.056*
C201.1985 (3)0.78579 (15)0.08902 (7)0.0403 (3)
C221.1318 (3)0.90707 (14)0.06459 (7)0.0445 (3)
H221.08760.96450.09670.053*
C211.0566 (3)0.73574 (15)0.13417 (7)0.0462 (4)
H210.92170.77720.14740.055*
C251.1310 (3)0.69572 (13)−0.12107 (6)0.0364 (3)
C130.6367 (3)0.29390 (16)0.28639 (7)0.0467 (3)
H130.63640.23830.25390.056*
C100.6416 (3)0.46247 (13)0.38252 (7)0.0384 (3)
C240.9560 (3)0.83310 (14)−0.04600 (7)0.0423 (3)
C260.9306 (3)0.68800 (14)−0.16549 (6)0.0406 (3)
H260.80090.7420−0.16450.049*
C20.8708 (3)0.30841 (17)0.63764 (9)0.0579 (4)
H20.92110.23290.65210.069*
C291.3159 (3)0.52760 (15)−0.16920 (8)0.0473 (4)
H291.44570.4737−0.17060.057*
C50.7174 (3)0.53523 (15)0.59396 (7)0.0439 (3)
C301.3245 (3)0.61452 (14)−0.12309 (7)0.0430 (3)
H301.45890.6189−0.09350.052*
C161.1176 (3)0.62478 (16)0.15900 (8)0.0501 (4)
C90.4602 (3)0.59164 (14)0.46030 (7)0.0433 (3)
C70.6352 (3)0.65669 (15)0.57293 (7)0.0477 (4)
H70.58680.70920.60670.057*
C80.5170 (3)0.68526 (15)0.51004 (8)0.0484 (4)
H80.40250.75320.50880.058*
C10.6677 (3)0.36400 (16)0.65992 (8)0.0509 (4)
C171.3165 (3)0.56100 (17)0.14013 (8)0.0560 (4)
H171.35540.48590.15710.067*
C140.8318 (3)0.29880 (17)0.33223 (8)0.0546 (4)
H140.96200.24520.33060.066*
C110.4450 (3)0.45718 (14)0.33707 (7)0.0446 (4)
H110.31430.51050.33850.053*
C40.9242 (3)0.48034 (18)0.57174 (8)0.0555 (4)
H41.01340.51930.54230.067*
C270.9252 (3)0.59935 (16)−0.21130 (7)0.0461 (4)
H270.79060.5940−0.24080.055*
C231.0199 (3)0.93147 (14)0.00091 (8)0.0463 (4)
H230.91221.0019−0.00280.056*
C191.3997 (3)0.72225 (16)0.07008 (7)0.0485 (4)
H191.49600.75480.04020.058*
C30.9960 (4)0.36815 (19)0.59349 (9)0.0620 (5)
H31.13250.33190.57790.074*
C181.4563 (3)0.61121 (17)0.09554 (8)0.0569 (4)
H181.59090.56930.08250.068*
C281.1165 (3)0.51936 (15)−0.21357 (7)0.0465 (4)
H281.11220.4604−0.24450.056*
C150.8354 (3)0.38212 (16)0.38009 (8)0.0484 (4)
H150.96690.38450.41060.058*
C120.4439 (3)0.37255 (15)0.28980 (7)0.0465 (4)
H120.31070.36870.25980.056*
H10.804 (2)0.578 (2)0.4432 (9)0.068 (6)*
H161.299 (2)0.8100 (17)−0.0620 (8)0.057 (5)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl20.0624 (3)0.0986 (4)0.0746 (3)−0.0042 (3)0.0055 (2)0.0396 (3)
Cl10.0844 (4)0.0729 (3)0.0736 (3)0.0089 (3)0.0196 (3)0.0186 (3)
N20.0410 (7)0.0456 (6)0.0381 (6)−0.0039 (6)0.0015 (5)−0.0040 (5)
O40.0458 (7)0.0632 (8)0.0550 (7)−0.0043 (6)0.0089 (5)−0.0090 (6)
O30.0640 (8)0.0475 (6)0.0487 (6)−0.0142 (5)0.0080 (5)−0.0033 (5)
O20.0684 (8)0.0541 (7)0.0502 (6)−0.0205 (6)0.0078 (6)−0.0091 (5)
O10.0466 (6)0.0663 (8)0.0527 (6)−0.0062 (6)0.0083 (5)−0.0134 (6)
N10.0435 (7)0.0504 (8)0.0411 (6)−0.0064 (6)0.0025 (5)−0.0109 (6)
C60.0432 (8)0.0540 (9)0.0422 (8)0.0039 (7)0.0029 (6)−0.0088 (7)
C200.0404 (8)0.0451 (7)0.0347 (7)−0.0003 (7)−0.0013 (5)−0.0062 (6)
C220.0544 (9)0.0407 (8)0.0387 (8)−0.0025 (7)0.0059 (7)−0.0073 (6)
C210.0426 (9)0.0527 (9)0.0433 (8)0.0036 (7)0.0033 (6)0.0012 (7)
C250.0375 (7)0.0392 (7)0.0327 (6)−0.0048 (6)0.0043 (5)0.0008 (6)
C130.0534 (9)0.0470 (8)0.0408 (8)−0.0052 (8)0.0096 (6)−0.0101 (7)
C100.0401 (8)0.0411 (7)0.0343 (7)−0.0047 (6)0.0047 (6)−0.0038 (6)
C240.0503 (9)0.0402 (7)0.0365 (7)−0.0025 (7)0.0041 (6)0.0023 (6)
C260.0413 (8)0.0456 (8)0.0347 (7)0.0025 (6)0.0010 (6)0.0027 (6)
C20.0575 (10)0.0558 (11)0.0589 (10)0.0108 (9)−0.0044 (8)−0.0112 (8)
C290.0414 (8)0.0453 (8)0.0560 (9)0.0021 (7)0.0097 (7)−0.0029 (7)
C50.0422 (8)0.0523 (9)0.0367 (7)−0.0031 (7)−0.0004 (6)−0.0134 (6)
C300.0356 (8)0.0489 (8)0.0443 (8)−0.0037 (6)0.0013 (6)0.0005 (7)
C160.0461 (9)0.0588 (10)0.0441 (8)−0.0067 (7)−0.0045 (7)0.0052 (7)
C90.0509 (9)0.0428 (8)0.0362 (7)−0.0029 (7)0.0031 (6)−0.0031 (6)
C70.0532 (9)0.0488 (8)0.0415 (8)−0.0052 (7)0.0065 (7)−0.0130 (7)
C80.0595 (10)0.0426 (8)0.0437 (8)−0.0021 (7)0.0071 (7)−0.0070 (7)
C10.0498 (9)0.0571 (10)0.0452 (8)−0.0007 (7)0.0001 (7)−0.0057 (7)
C170.0622 (10)0.0495 (9)0.0540 (9)0.0070 (8)−0.0099 (8)0.0016 (8)
C140.0404 (8)0.0599 (10)0.0640 (10)0.0072 (8)0.0066 (7)−0.0137 (9)
C110.0481 (9)0.0469 (8)0.0376 (8)0.0080 (7)−0.0030 (6)−0.0010 (6)
C40.0454 (9)0.0731 (11)0.0487 (9)−0.0022 (8)0.0086 (7)−0.0116 (8)
C270.0444 (9)0.0590 (10)0.0343 (7)−0.0092 (7)−0.0006 (6)0.0003 (7)
C230.0557 (9)0.0383 (7)0.0451 (8)0.0016 (7)0.0057 (7)−0.0007 (6)
C190.0438 (9)0.0607 (10)0.0413 (8)0.0030 (7)0.0042 (6)−0.0066 (7)
C30.0488 (10)0.0725 (12)0.0648 (11)0.0149 (9)0.0050 (8)−0.0172 (10)
C180.0538 (10)0.0642 (11)0.0520 (9)0.0178 (8)−0.0001 (8)−0.0079 (8)
C280.0553 (10)0.0442 (8)0.0414 (8)−0.0111 (7)0.0119 (7)−0.0069 (6)
C150.0358 (8)0.0588 (10)0.0500 (9)−0.0003 (7)−0.0013 (6)−0.0076 (7)
C120.0525 (10)0.0515 (9)0.0344 (7)0.0001 (7)−0.0043 (6)−0.0018 (6)

Geometric parameters (Å, °)

Cl2—C161.7446 (18)C26—H260.9300
Cl1—C11.7419 (19)C2—C31.376 (3)
N2—C241.344 (2)C2—C11.384 (2)
N2—C251.4231 (19)C2—H20.9300
N2—H160.886 (9)C29—C301.379 (2)
O4—C241.2198 (19)C29—C281.387 (2)
O3—C231.435 (2)C29—H290.9300
O3—C221.4388 (19)C5—C41.397 (2)
O2—C71.437 (2)C5—C71.484 (2)
O2—C81.439 (2)C30—H300.9300
O1—C91.220 (2)C16—C171.382 (3)
N1—C91.342 (2)C9—C81.503 (2)
N1—C101.4237 (19)C7—C81.476 (2)
N1—H10.898 (9)C7—H70.9800
C6—C11.378 (2)C8—H80.9800
C6—C51.394 (2)C17—C181.382 (3)
C6—H60.9300C17—H170.9300
C20—C191.391 (2)C14—C151.379 (2)
C20—C211.397 (2)C14—H140.9300
C20—C221.484 (2)C11—C121.380 (2)
C22—C231.469 (2)C11—H110.9300
C22—H220.9800C4—C31.380 (3)
C21—C161.376 (2)C4—H40.9300
C21—H210.9300C27—C281.376 (3)
C25—C261.391 (2)C27—H270.9300
C25—C301.393 (2)C23—H230.9800
C13—C121.374 (2)C19—C181.377 (3)
C13—C141.388 (2)C19—H190.9300
C13—H130.9300C3—H30.9300
C10—C111.388 (2)C18—H180.9300
C10—C151.388 (2)C28—H280.9300
C24—C231.506 (2)C15—H150.9300
C26—C271.388 (2)C12—H120.9300
C24—N2—C25125.48 (13)N1—C9—C8116.11 (14)
C24—N2—H16119.6 (12)O2—C7—C859.18 (11)
C25—N2—H16114.7 (12)O2—C7—C5117.74 (14)
C23—O3—C2261.51 (10)C8—C7—C5124.83 (13)
C7—O2—C861.78 (11)O2—C7—H7114.5
C9—N1—C10125.66 (13)C8—C7—H7114.5
C9—N1—H1119.0 (14)C5—C7—H7114.5
C10—N1—H1115.4 (14)O2—C8—C759.04 (11)
C1—C6—C5119.83 (15)O2—C8—C9118.44 (14)
C1—C6—H6120.1C7—C8—C9122.83 (14)
C5—C6—H6120.1O2—C8—H8115.0
C19—C20—C21119.18 (15)C7—C8—H8115.0
C19—C20—C22122.63 (14)C9—C8—H8115.0
C21—C20—C22118.17 (14)C6—C1—C2121.74 (17)
O3—C22—C2359.11 (10)C6—C1—Cl1119.94 (14)
O3—C22—C20117.82 (13)C2—C1—Cl1118.31 (14)
C23—C22—C20124.43 (13)C16—C17—C18118.58 (17)
O3—C22—H22114.6C16—C17—H17120.7
C23—C22—H22114.6C18—C17—H17120.7
C20—C22—H22114.6C15—C14—C13120.88 (16)
C16—C21—C20119.60 (16)C15—C14—H14119.6
C16—C21—H21120.2C13—C14—H14119.6
C20—C21—H21120.2C12—C11—C10119.85 (15)
C26—C25—C30119.64 (13)C12—C11—H11120.1
C26—C25—N2121.50 (13)C10—C11—H11120.1
C30—C25—N2118.84 (13)C3—C4—C5119.86 (18)
C12—C13—C14118.97 (15)C3—C4—H4120.1
C12—C13—H13120.5C5—C4—H4120.1
C14—C13—H13120.5C28—C27—C26120.77 (14)
C11—C10—C15119.60 (14)C28—C27—H27119.6
C11—C10—N1121.55 (14)C26—C27—H27119.6
C15—C10—N1118.84 (13)O3—C23—C2259.38 (10)
O4—C24—N2125.52 (14)O3—C23—C24118.15 (14)
O4—C24—C23119.07 (15)C22—C23—C24122.42 (13)
N2—C24—C23115.39 (14)O3—C23—H23115.1
C27—C26—C25119.72 (14)C22—C23—H23115.1
C27—C26—H26120.1C24—C23—H23115.1
C25—C26—H26120.1C18—C19—C20120.05 (16)
C3—C2—C1118.03 (17)C18—C19—H19120.0
C3—C2—H2121.0C20—C19—H19120.0
C1—C2—H2121.0C2—C3—C4121.72 (17)
C30—C29—C28120.94 (15)C2—C3—H3119.1
C30—C29—H29119.5C4—C3—H3119.1
C28—C29—H29119.5C19—C18—C17121.11 (17)
C6—C5—C4118.79 (16)C19—C18—H18119.4
C6—C5—C7119.21 (14)C17—C18—H18119.4
C4—C5—C7121.95 (16)C27—C28—C29119.25 (15)
C29—C30—C25119.69 (14)C27—C28—H28120.4
C29—C30—H30120.2C29—C28—H28120.4
C25—C30—H30120.2C14—C15—C10119.71 (14)
C21—C16—C17121.48 (17)C14—C15—H15120.1
C21—C16—Cl2118.95 (14)C10—C15—H15120.1
C17—C16—Cl2119.56 (13)C13—C12—C11120.99 (15)
O1—C9—N1125.40 (14)C13—C12—H12119.5
O1—C9—C8118.47 (14)C11—C12—H12119.5
C23—O3—C22—C20115.43 (15)O1—C9—C8—C7106.3 (2)
C19—C20—C22—O33.3 (2)N1—C9—C8—C7−75.2 (2)
C21—C20—C22—O3−178.56 (13)C5—C6—C1—C20.5 (2)
C19—C20—C22—C2373.3 (2)C5—C6—C1—Cl1−179.73 (12)
C21—C20—C22—C23−108.56 (18)C3—C2—C1—C60.0 (3)
C19—C20—C21—C16−0.1 (2)C3—C2—C1—Cl1−179.76 (14)
C22—C20—C21—C16−178.28 (14)C21—C16—C17—C180.4 (2)
C24—N2—C25—C2635.2 (2)Cl2—C16—C17—C18−179.17 (13)
C24—N2—C25—C30−146.60 (14)C12—C13—C14—C15−0.9 (3)
C9—N1—C10—C1136.7 (2)C15—C10—C11—C12−0.2 (2)
C9—N1—C10—C15−144.72 (16)N1—C10—C11—C12178.34 (15)
C25—N2—C24—O4−0.2 (2)C6—C5—C4—C31.4 (2)
C25—N2—C24—C23−178.62 (13)C7—C5—C4—C3178.88 (15)
C30—C25—C26—C270.1 (2)C25—C26—C27—C28−0.4 (2)
N2—C25—C26—C27178.31 (14)C22—O3—C23—C24−112.95 (15)
C1—C6—C5—C4−1.2 (2)C20—C22—C23—O3−104.43 (17)
C1—C6—C5—C7−178.74 (14)O3—C22—C23—C24105.87 (17)
C28—C29—C30—C25−0.3 (2)C20—C22—C23—C241.4 (3)
C26—C25—C30—C290.2 (2)O4—C24—C23—O3173.79 (14)
N2—C25—C30—C29−178.00 (14)N2—C24—C23—O3−7.7 (2)
C20—C21—C16—C17−0.2 (2)O4—C24—C23—C22103.94 (19)
C20—C21—C16—Cl2179.30 (12)N2—C24—C23—C22−77.5 (2)
C10—N1—C9—O1−1.3 (3)C21—C20—C19—C180.3 (2)
C10—N1—C9—C8−179.71 (14)C22—C20—C19—C18178.39 (14)
C8—O2—C7—C5115.96 (15)C1—C2—C3—C40.2 (3)
C6—C5—C7—O2179.81 (14)C5—C4—C3—C2−0.9 (3)
C4—C5—C7—O22.4 (2)C20—C19—C18—C17−0.2 (3)
C6—C5—C7—C8−110.02 (19)C16—C17—C18—C19−0.2 (3)
C4—C5—C7—C872.5 (2)C26—C27—C28—C290.4 (2)
C7—O2—C8—C9−113.21 (16)C30—C29—C28—C270.0 (2)
C5—C7—C8—O2−104.19 (18)C13—C14—C15—C10−0.1 (3)
O2—C7—C8—C9105.89 (18)C11—C10—C15—C140.7 (2)
C5—C7—C8—C91.7 (3)N1—C10—C15—C14−177.90 (16)
O1—C9—C8—O2175.98 (14)C14—C13—C12—C111.4 (3)
N1—C9—C8—O2−5.5 (2)C10—C11—C12—C13−0.9 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.90 (1)2.41 (1)3.2287 (15)152
N2—H16···O4i0.89 (1)2.40 (1)3.2357 (16)156
C4—H4···O1i0.932.493.388 (2)162
C15—H15···O1i0.932.583.259 (2)130
C19—H19···O4i0.932.593.5087 (19)168

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2659).

References

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