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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3000.
Published online 2009 November 7. doi:  10.1107/S160053680904584X
PMCID: PMC2971788

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

Abstract

There are two independent mol­ecules in the asymmetric unit of the title compound, C15H12BrNO2. In both mol­ecules, the two benzene rings adopt a cis configuration with respect to the ep­oxy ring. In one mol­ecule, the ep­oxy ring makes dihedral angles of 60.5 (2) and 77.92 (19)° with the two benzene rings; in the other mol­ecule, the values are 61.0 (2) and 81.43 (19)°. Inter­molecular N—H(...)O and C—H(...)O hydrogen bonding is present in the crystal structure.

Related literature

For epoxide-containing compounds used as building blocks in synthesis, see: Diez et al. (2008 [triangle]); Watanabe et al. (1998 [triangle]); Zhu & Espenson (1995 [triangle]). For related structures, see: He (2009 [triangle]); He & Chen (2009 [triangle]).

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Object name is e-65-o3000-scheme1.jpg

Experimental

Crystal data

  • C15H12BrNO2
  • M r = 318.17
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3000-efi1.jpg
  • a = 5.5124 (1) Å
  • b = 11.1975 (2) Å
  • c = 21.3298 (4) Å
  • β = 94.405 (2)°
  • V = 1312.69 (4) Å3
  • Z = 4
  • Cu Kα radiation
  • μ = 4.25 mm−1
  • T = 295 K
  • 0.36 × 0.34 × 0.30 mm

Data collection

  • Oxford Diffraction Gemini S Ultra diffractometer
  • Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 [triangle]) T min = 0.310, T max = 0.362
  • 19177 measured reflections
  • 4142 independent reflections
  • 4027 reflections with I > 2σ(I)
  • R int = 0.048

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.084
  • S = 1.00
  • 4142 reflections
  • 351 parameters
  • 17 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.67 e Å−3
  • Δρmin = −0.38 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1768 Friedel pairs
  • Flack parameter: 0.016 (18)

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/S160053680904584X/xu2663sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680904584X/xu2663Isup2.hkl

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

Acknowledgments

The diffraction data were collected at The Centre for Testing and Analysis, Sichuan University. We acknowledge financial support from China West Normal University.

supplementary crystallographic information

Comment

α, β-Epoxy carbonyl compound are important intermediates for the synthesis of complex molecules. (Diez et al. 2008; Watanabe et al. 1998). The Darzens reaction, is one of the most powerful method to the synthesis of α, β-epoxy carbonyl and related compounds (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 is 86.13 (10)° and that between C16–21 and C25–30 phenyl ring is 83.86 (11)°. O2/C7/C8 epoxide ring makes dihedral angles of 60.47 (22)° and 77.92 (19)° with C6 and C15 phenyl ring, respectively. O3/C22/C23 epoxide ring makes dihedral angles of 60.96 (22)° and 81.43 (19)° with C16 and C25 phenyl ring, respectively. 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-bromophenylaldehyde (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 1 d.

Refinement

H atoms on N atoms was located in a difference Fourier map and refined isotropically with distance restraints of 0.90±0.01 Å. The carbon-bound hydrogen atoms were placed in calculated positions with C—H = 0.93–0.98 Å and refined using a riding model, Uiso(H) =1.2Ueq(C). The distance restraints of 1.39±0.01 Å were applied for the C—C bonds of the benzene rings.

Figures

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

Crystal data

C15H12BrNO2F(000) = 640
Mr = 318.17Dx = 1.610 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2ybCell parameters from 15364 reflections
a = 5.5124 (1) Åθ = 2.1–71.8°
b = 11.1975 (2) ŵ = 4.25 mm1
c = 21.3298 (4) ÅT = 295 K
β = 94.405 (2)°Block, colorless
V = 1312.69 (4) Å30.36 × 0.34 × 0.30 mm
Z = 4

Data collection

Oxford Diffraction Gemini S Ultra diffractometer4142 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source4027 reflections with I > 2σ(I)
mirrorRint = 0.048
Detector resolution: 15.9149 pixels mm-1θmax = 65.1°, θmin = 2.1°
ω scansh = −6→6
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)k = −13→10
Tmin = 0.310, Tmax = 0.362l = −25→25
19177 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)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.084w = 1/[σ2(Fo2) + (0.0457P)2 + 0.857P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
4142 reflectionsΔρmax = 0.67 e Å3
351 parametersΔρmin = −0.38 e Å3
17 restraintsAbsolute structure: Flack (1983), 1768 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.016 (18)

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
Br10.42656 (10)0.89013 (4)0.78262 (2)0.07080 (18)
Br20.99441 (11)0.66221 (5)0.71660 (2)0.07210 (17)
O30.7352 (6)0.2259 (3)0.52366 (13)0.0628 (8)
N20.8472 (5)0.3942 (3)0.42997 (14)0.0468 (7)
N10.6413 (5)0.6562 (3)1.07453 (13)0.0453 (7)
O20.7701 (6)0.4874 (3)0.98389 (13)0.0584 (8)
O10.2403 (5)0.6400 (3)1.05633 (13)0.0589 (8)
O41.2515 (5)0.3825 (3)0.44653 (13)0.0592 (7)
C100.6238 (6)0.7481 (3)1.12127 (15)0.0396 (8)
C170.9052 (7)0.4659 (4)0.63585 (17)0.0465 (9)
H171.04990.43440.65420.056*
C70.6277 (7)0.5369 (4)0.93584 (17)0.0457 (9)
H70.57520.48030.90250.055*
C250.8600 (6)0.4843 (3)0.38192 (15)0.0409 (8)
C130.6069 (7)0.9245 (4)1.21235 (17)0.0468 (10)
H130.60940.98661.24130.056*
C10.6161 (7)0.8207 (4)0.84397 (17)0.0466 (9)
C30.9538 (8)0.8303 (4)0.90649 (19)0.0554 (11)
H31.09700.86780.92160.066*
C50.6970 (6)0.6577 (4)0.91201 (15)0.0410 (7)
C160.8251 (7)0.5765 (4)0.65623 (18)0.0489 (9)
C60.5555 (7)0.7099 (4)0.86780 (17)0.0453 (9)
H60.41300.67230.85220.054*
C80.5158 (8)0.5125 (4)0.99944 (19)0.0490 (9)
H80.41080.44180.99930.059*
C230.9853 (8)0.2580 (4)0.50714 (18)0.0509 (9)
H231.09990.19100.50970.061*
C140.8076 (7)0.9150 (4)1.16933 (18)0.0528 (10)
H140.93260.97091.17360.063*
C40.8971 (7)0.7199 (4)0.93112 (18)0.0496 (9)
H41.00350.68740.96250.060*
C261.0499 (7)0.4918 (4)0.33747 (17)0.0460 (9)
H261.17620.43650.34070.055*
C150.8182 (6)0.8273 (3)1.12322 (17)0.0459 (9)
H150.94320.82231.09640.055*
C110.4279 (7)0.7575 (4)1.16434 (16)0.0447 (8)
H110.30170.70221.16080.054*
C180.7812 (6)0.4049 (4)0.59137 (16)0.0445 (9)
C20.8138 (7)0.8835 (4)0.86286 (18)0.0513 (9)
H20.84870.95810.84650.062*
C210.6217 (8)0.6303 (4)0.6342 (2)0.0601 (12)
H210.57260.70440.64840.072*
C271.0480 (7)0.5783 (4)0.29070 (17)0.0475 (10)
H271.16870.58280.26270.057*
C280.8594 (8)0.6554 (4)0.28868 (16)0.0508 (9)
H280.84980.71510.25830.061*
C90.4518 (7)0.6102 (4)1.04614 (16)0.0444 (8)
C300.6630 (6)0.5628 (4)0.38105 (18)0.0490 (9)
H300.54250.55880.40920.059*
C290.6667 (7)0.6478 (4)0.33342 (18)0.0568 (10)
H290.54070.70320.32940.068*
C200.4981 (8)0.5692 (5)0.5910 (2)0.0623 (12)
H200.35270.60110.57340.075*
C120.4244 (7)0.8461 (4)1.21031 (16)0.0505 (11)
H120.30190.85031.23790.061*
C241.0405 (7)0.3523 (3)0.45838 (16)0.0460 (9)
C190.5729 (7)0.4571 (5)0.56933 (19)0.0575 (11)
H190.47400.41780.53860.069*
C220.8683 (8)0.2850 (4)0.57056 (18)0.0499 (9)
H220.92860.23330.60540.060*
H1A0.779 (4)0.631 (3)1.0586 (16)0.038 (10)*
H2A0.710 (5)0.369 (4)0.4461 (18)0.055 (12)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0567 (3)0.0843 (4)0.0696 (3)0.0040 (3)−0.00674 (19)0.0319 (3)
Br20.0783 (3)0.0641 (3)0.0704 (3)0.0098 (3)−0.0172 (2)−0.0138 (3)
O30.079 (2)0.0537 (18)0.0527 (16)−0.0231 (16)−0.0157 (14)0.0082 (14)
N20.0472 (16)0.052 (2)0.0402 (15)−0.0079 (18)−0.0066 (12)0.0116 (15)
N10.0473 (16)0.0487 (19)0.0381 (14)0.0032 (17)−0.0079 (12)−0.0073 (15)
O20.075 (2)0.0446 (18)0.0516 (16)0.0170 (15)−0.0173 (14)−0.0015 (12)
O10.0532 (16)0.063 (2)0.0580 (16)0.0031 (15)−0.0148 (13)−0.0066 (14)
O40.0515 (15)0.0659 (19)0.0575 (15)−0.0072 (17)−0.0142 (12)0.0116 (16)
C100.0419 (18)0.040 (2)0.0352 (17)0.0040 (15)−0.0104 (14)0.0030 (15)
C170.0401 (18)0.051 (2)0.0463 (19)0.0012 (17)−0.0063 (15)0.0068 (18)
C70.052 (2)0.040 (2)0.0423 (19)0.0012 (17)−0.0148 (16)−0.0033 (16)
C250.0436 (18)0.040 (2)0.0369 (17)−0.0055 (16)−0.0105 (14)0.0013 (14)
C130.056 (2)0.044 (2)0.0374 (18)0.0146 (18)−0.0198 (16)−0.0074 (16)
C10.0414 (19)0.053 (2)0.0445 (18)0.0058 (17)−0.0029 (15)0.0018 (17)
C30.051 (2)0.064 (3)0.050 (2)−0.018 (2)−0.0049 (18)−0.0047 (19)
C50.0401 (17)0.045 (2)0.0374 (16)0.0005 (18)−0.0034 (13)−0.0044 (17)
C160.046 (2)0.052 (2)0.048 (2)0.0001 (18)−0.0019 (16)0.0050 (17)
C60.0415 (19)0.049 (2)0.0438 (19)−0.0016 (16)−0.0088 (15)0.0017 (16)
C80.061 (2)0.037 (2)0.047 (2)−0.0014 (17)−0.0124 (17)0.0010 (16)
C230.064 (2)0.039 (2)0.047 (2)−0.0017 (18)−0.0135 (18)0.0049 (17)
C140.045 (2)0.050 (3)0.061 (2)−0.0024 (17)−0.0171 (17)−0.0015 (19)
C40.042 (2)0.061 (3)0.0439 (19)−0.0022 (18)−0.0104 (16)−0.0056 (18)
C260.047 (2)0.047 (2)0.0424 (19)0.0085 (17)−0.0033 (16)0.0007 (17)
C150.0355 (18)0.052 (2)0.049 (2)0.0028 (16)−0.0054 (15)0.0000 (17)
C110.0435 (19)0.047 (2)0.0422 (18)−0.0048 (16)−0.0080 (15)0.0024 (16)
C180.0385 (16)0.053 (2)0.0408 (17)−0.0023 (18)−0.0057 (13)0.0110 (17)
C20.052 (2)0.050 (2)0.0514 (19)−0.007 (2)0.0005 (16)−0.0005 (19)
C210.054 (2)0.063 (3)0.062 (2)0.014 (2)−0.003 (2)0.011 (2)
C270.051 (2)0.058 (3)0.0344 (18)−0.0067 (19)0.0053 (15)−0.0034 (17)
C280.070 (2)0.041 (2)0.0371 (17)−0.005 (2)−0.0193 (16)0.0108 (18)
C90.054 (2)0.041 (2)0.0368 (17)0.0025 (16)−0.0072 (16)0.0011 (15)
C300.0352 (18)0.058 (3)0.053 (2)−0.0027 (17)−0.0036 (15)0.0046 (18)
C290.0449 (19)0.058 (3)0.064 (2)0.005 (2)−0.0154 (17)0.008 (2)
C200.046 (2)0.077 (3)0.063 (3)0.013 (2)−0.0062 (19)0.015 (2)
C120.052 (2)0.066 (3)0.0327 (17)0.017 (2)−0.0002 (15)0.0021 (17)
C240.058 (2)0.042 (2)0.0359 (17)−0.0058 (17)−0.0065 (16)0.0031 (15)
C190.043 (2)0.078 (3)0.049 (2)−0.002 (2)−0.0131 (17)0.013 (2)
C220.058 (2)0.047 (2)0.0426 (19)−0.0070 (18)−0.0147 (17)0.0087 (17)

Geometric parameters (Å, °)

Br1—C11.788 (4)C5—C41.341 (5)
Br2—C161.807 (4)C16—C211.326 (6)
O3—C221.365 (5)C6—H60.9300
O3—C231.493 (6)C8—C91.539 (6)
N2—C241.274 (5)C8—H80.9800
N2—C251.444 (5)C23—C241.528 (5)
N2—H2A0.90 (3)C23—C221.572 (6)
N1—C91.275 (5)C23—H230.9800
N1—C101.442 (5)C14—C151.395 (5)
N1—H1A0.90 (3)C14—H140.9300
O2—C71.360 (4)C4—H40.9300
O2—C81.492 (5)C26—C271.390 (5)
O1—C91.248 (5)C26—H260.9300
O4—C241.256 (5)C15—H150.9300
C10—C151.389 (5)C11—C121.397 (5)
C10—C111.474 (5)C11—H110.9300
C17—C181.317 (5)C18—C191.341 (5)
C17—C161.396 (6)C18—C221.504 (6)
C17—H170.9300C2—H20.9300
C7—C51.505 (6)C21—C201.298 (7)
C7—C81.557 (6)C21—H210.9300
C7—H70.9800C27—C281.349 (5)
C25—C301.396 (5)C27—H270.9300
C25—C261.468 (5)C28—C291.484 (5)
C13—C121.333 (6)C28—H280.9300
C13—C141.494 (5)C30—C291.393 (5)
C13—H130.9300C30—H300.9300
C1—C21.333 (5)C29—H290.9300
C1—C61.392 (6)C20—C191.411 (7)
C3—C21.306 (6)C20—H200.9300
C3—C41.388 (6)C12—H120.9300
C3—H30.9300C19—H190.9300
C5—C61.314 (5)C22—H220.9800
C22—O3—C2366.6 (3)C13—C14—H14118.1
C24—N2—C25120.7 (3)C5—C4—C3123.5 (4)
C24—N2—H2A113 (3)C5—C4—H4118.3
C25—N2—H2A125 (3)C3—C4—H4118.3
C9—N1—C10121.4 (3)C27—C26—C25122.5 (3)
C9—N1—H1A112 (2)C27—C26—H26118.8
C10—N1—H1A126 (3)C25—C26—H26118.8
C7—O2—C866.0 (3)C10—C15—C14113.3 (3)
C15—C10—N1112.6 (3)C10—C15—H15123.3
C15—C10—C11122.5 (3)C14—C15—H15123.3
N1—C10—C11124.9 (3)C12—C11—C10122.6 (3)
C18—C17—C16121.7 (4)C12—C11—H11118.7
C18—C17—H17119.2C10—C11—H11118.7
C16—C17—H17119.2C17—C18—C19114.2 (4)
O2—C7—C5118.3 (3)C17—C18—C22121.0 (3)
O2—C7—C861.1 (3)C19—C18—C22124.7 (4)
C5—C7—C8125.5 (3)C3—C2—C1113.5 (4)
O2—C7—H7113.9C3—C2—H2123.2
C5—C7—H7113.9C1—C2—H2123.2
C8—C7—H7113.9C20—C21—C16113.3 (5)
C30—C25—N2111.6 (3)C20—C21—H21123.3
C30—C25—C26123.2 (3)C16—C21—H21123.3
N2—C25—C26125.1 (3)C28—C27—C26115.6 (4)
C12—C13—C14121.7 (4)C28—C27—H27122.2
C12—C13—H13119.1C26—C27—H27122.2
C14—C13—H13119.1C27—C28—C29122.1 (4)
C2—C1—C6125.0 (4)C27—C28—H28119.0
C2—C1—Br1114.2 (3)C29—C28—H28119.0
C6—C1—Br1120.8 (3)O1—C9—N1123.5 (4)
C2—C3—C4122.6 (4)O1—C9—C8124.5 (4)
C2—C3—H3118.7N1—C9—C8112.0 (4)
C4—C3—H3118.7C29—C30—C25112.6 (3)
C6—C5—C4114.6 (4)C29—C30—H30123.7
C6—C5—C7119.4 (3)C25—C30—H30123.7
C4—C5—C7126.0 (3)C30—C29—C28124.0 (4)
C21—C16—C17124.9 (4)C30—C29—H29118.0
C21—C16—Br2112.8 (3)C28—C29—H29118.0
C17—C16—Br2122.3 (3)C21—C20—C19123.4 (4)
C5—C6—C1120.9 (4)C21—C20—H20118.3
C5—C6—H6119.6C19—C20—H20118.3
C1—C6—H6119.6C13—C12—C11116.1 (4)
O2—C8—C9123.0 (3)C13—C12—H12122.0
O2—C8—C753.0 (2)C11—C12—H12122.0
C9—C8—C7124.4 (3)O4—C24—N2123.9 (4)
O2—C8—H8114.3O4—C24—C23124.0 (4)
C9—C8—H8114.3N2—C24—C23112.1 (4)
C7—C8—H8114.3C18—C19—C20122.5 (4)
O3—C23—C24124.2 (3)C18—C19—H19118.8
O3—C23—C2252.8 (2)C20—C19—H19118.8
C24—C23—C22124.7 (4)O3—C22—C18118.9 (3)
O3—C23—H23113.9O3—C22—C2360.6 (3)
C24—C23—H23113.9C18—C22—C23125.9 (3)
C22—C23—H23113.9O3—C22—H22113.6
C15—C14—C13123.8 (4)C18—C22—H22113.6
C15—C14—H14118.1C23—C22—H22113.6
C9—N1—C10—C15−148.8 (4)Br1—C1—C2—C3−178.3 (3)
C9—N1—C10—C1133.1 (5)C17—C16—C21—C200.5 (7)
C8—O2—C7—C5117.1 (4)Br2—C16—C21—C20−179.7 (4)
C24—N2—C25—C30−147.1 (4)C25—C26—C27—C28−0.1 (6)
C24—N2—C25—C2634.9 (5)C26—C27—C28—C29−0.1 (6)
O2—C7—C5—C6−176.6 (4)C10—N1—C9—O1−0.2 (6)
C8—C7—C5—C6−103.5 (4)C10—N1—C9—C8−178.9 (3)
O2—C7—C5—C44.3 (6)O2—C8—C9—O1173.9 (4)
C8—C7—C5—C477.4 (5)C7—C8—C9—O1109.1 (5)
C18—C17—C16—C210.5 (7)O2—C8—C9—N1−7.5 (5)
C18—C17—C16—Br2−179.3 (3)C7—C8—C9—N1−72.2 (5)
C4—C5—C6—C10.2 (6)N2—C25—C30—C29−177.7 (3)
C7—C5—C6—C1−179.0 (3)C26—C25—C30—C290.3 (5)
C2—C1—C6—C5−0.6 (6)C25—C30—C29—C28−0.5 (6)
Br1—C1—C6—C5178.7 (3)C27—C28—C29—C300.5 (7)
C7—O2—C8—C9−110.7 (4)C16—C21—C20—C19−0.3 (7)
C5—C7—C8—O2−105.8 (4)C14—C13—C12—C11−2.0 (6)
O2—C7—C8—C9108.0 (4)C10—C11—C12—C131.4 (6)
C5—C7—C8—C92.3 (6)C25—N2—C24—O4−1.6 (6)
C22—O3—C23—C24−110.4 (4)C25—N2—C24—C23−179.8 (3)
C12—C13—C14—C151.7 (6)O3—C23—C24—O4176.9 (4)
C6—C5—C4—C3−0.3 (6)C22—C23—C24—O4111.6 (5)
C7—C5—C4—C3178.8 (4)O3—C23—C24—N2−4.9 (6)
C2—C3—C4—C50.9 (7)C22—C23—C24—N2−70.1 (5)
C30—C25—C26—C270.0 (6)C17—C18—C19—C201.7 (6)
N2—C25—C26—C27177.7 (4)C22—C18—C19—C20179.2 (4)
N1—C10—C15—C14−178.4 (3)C21—C20—C19—C18−0.8 (7)
C11—C10—C15—C14−0.2 (5)C23—O3—C22—C18117.3 (4)
C13—C14—C15—C10−0.4 (5)C17—C18—C22—O3−179.1 (4)
C15—C10—C11—C12−0.3 (5)C19—C18—C22—O33.5 (6)
N1—C10—C11—C12177.7 (3)C17—C18—C22—C23−106.1 (4)
C16—C17—C18—C19−1.5 (6)C19—C18—C22—C2376.5 (6)
C16—C17—C18—C22−179.1 (4)C24—C23—C22—O3109.5 (4)
C4—C3—C2—C1−1.1 (6)O3—C23—C22—C18−106.1 (4)
C6—C1—C2—C31.0 (6)C24—C23—C22—C183.4 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.90 (3)2.55 (2)3.359 (4)150
N2—H2A···O4ii0.90 (3)2.53 (2)3.332 (4)148
C3—H3···O2iii0.932.483.214 (5)136
C4—H4···O1i0.932.363.277 (5)167
C19—H19···O4ii0.932.273.160 (5)160
C20—H20···O3iv0.932.513.199 (6)131

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2663).

References

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