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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o2916.
Published online 2010 October 23. doi:  10.1107/S1600536810040742
PMCID: PMC3009098

Ethyl 4-[(3,5-di-tert-butyl-2-hy­droxy­benz­yl)amino]­benzoate

Abstract

The title amine, C24H33NO3, has two substituted aromatic rings at either end of the –CH2NH– linkage [Car­yl–CH2–NH–Car­yl torsion angle = 77.4 (3)°]. The amino and hy­droxy groups are hydrogen-bond donors to the carbonyl O atom of an adjacent mol­ecule. These hydrogen bonds give rise to a chain that runs along the b axis. One of the tert-butyl groups is disordered over two positions with a site-occupation factor of 0.834 (6) for the major occupied site.

Related literature

For the structure of the Schiff-base reactant, see: Shakir et al. (2010 [triangle]).

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Object name is e-66-o2916-scheme1.jpg

Experimental

Crystal data

  • C24H33NO3
  • M r = 383.51
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2916-efi1.jpg
  • a = 17.788 (3) Å
  • b = 8.9872 (14) Å
  • c = 14.235 (2) Å
  • β = 101.414 (2)°
  • V = 2230.7 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 100 K
  • 0.30 × 0.10 × 0.03 mm

Data collection

  • Bruker SMART APEX diffractometer
  • 17094 measured reflections
  • 3928 independent reflections
  • 2428 reflections with I > 2σ(I)
  • R int = 0.092

Refinement

  • R[F 2 > 2σ(F 2)] = 0.058
  • wR(F 2) = 0.154
  • S = 1.03
  • 3928 reflections
  • 283 parameters
  • 45 restraints
  • H-atom parameters constrained
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810040742/bt5371sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040742/bt5371Isup2.hkl

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

Acknowledgments

We thank the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The Schiff base, ethyl 4-(di-3,5-tert-butyl-2-hydroxybenzylideneamino)benzoate, is an intensely orange-colored compound whose color can be attributed to the azomethine double-bond; in the crystal structure, the two aromatic rings are aligned at 24.9 (1) ° (Shakir et al., 2010). The reduction of this compound affords the title colorless compound (Scheme I, Fig. 1), which is a secondary amine. The amino and hydroxy groups are hydrogen-bond donors to the carbonyl oxygen atom of an adjacent molecule; the hydrogen bonds give rise to a chain that runs along the b-axis. One of the tert-butyl groups is disordered over two positions with respect to the methyl units in an 83.6 (6):16.4 (6) ratio.

Experimental

Ethyl 4-aminobenzoate (0.35 g) dissolved in ethanol (5 ml) was added to 3,5-di-tert-butyl-2-hydroxybenzaldehyde (0.5 g) dissolved in ethanol (20 ml). Several drops of acetic acid were added. The solution was heated for 3 h. The solvent was evaporated and the product recrystallized from ethanol to yield orange prisms in 80% yield. The compound (0.5 g) was dissolved in methanol-THF (1:1) (20 ml). The solution was cooled to 273 K and three equivalents of sodium tetraborate were added. The mixture was stirred for 4 h until the orange color was discharged. The mixture was filtered and the solvent evaporated. The colorless compound was recrystallized from a hexane-ethanol mixure (yield 90%).

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95–0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–15U(C).

The amino and hydroxy H-atoms were also placed in calculated positions and their displacement parameters were also similarly tied (N–H 0.88 Å and O–H 0.84 Å).

One of the tert-butyl groups is disordered over two positions with respect to the methyl units in an 83.4 (6):16.6 (6) ratio; the C–Cmethyl distances were restrained to 1.50±0.01 Å; the anisotroic displacement parameters of the six methyl C-atoms were restrained to be nearly isotropic. By the use of a SAME instruction, the bonds involving the C12', C13' and C14' were restrained to the same length as those involving the unprimed ones. In addition, the 1,3-related distances were restrained to be equal in both disordered moieties.

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of C24H33NO3 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in one of the tert-butyl groups is not shown.
Fig. 2.
Hydrogen-bonded chain motif.

Crystal data

C24H33NO3F(000) = 832
Mr = 383.51Dx = 1.142 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1466 reflections
a = 17.788 (3) Åθ = 2.1–21.3°
b = 8.9872 (14) ŵ = 0.07 mm1
c = 14.235 (2) ÅT = 100 K
β = 101.414 (2)°Prism, colorless
V = 2230.7 (6) Å30.30 × 0.10 × 0.03 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer2428 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.092
graphiteθmax = 25.0°, θmin = 2.3°
ω scansh = −20→21
17094 measured reflectionsk = −10→10
3928 independent reflectionsl = −16→16

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.154w = 1/[σ2(Fo2) + (0.0662P)2 + 0.7154P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
3928 reflectionsΔρmax = 0.24 e Å3
283 parametersΔρmin = −0.23 e Å3
45 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0079 (12)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
O10.32463 (11)0.7157 (2)0.42898 (14)0.0281 (5)
H1O0.36130.71450.39980.042*
O20.46605 (11)−0.2040 (2)0.36814 (13)0.0257 (5)
O30.58429 (11)−0.1107 (2)0.41969 (13)0.0237 (5)
N10.41764 (13)0.5020 (2)0.31779 (16)0.0223 (6)
H1N0.44970.56900.34790.027*
C10.26841 (16)0.6193 (3)0.38515 (19)0.0206 (6)
C20.20301 (16)0.6027 (3)0.4259 (2)0.0224 (7)
C30.14725 (16)0.5024 (3)0.3809 (2)0.0246 (7)
H30.10280.48900.40760.029*
C40.15296 (16)0.4208 (3)0.2993 (2)0.0227 (7)
C50.21844 (16)0.4441 (3)0.2617 (2)0.0227 (7)
H50.22360.39200.20520.027*
C60.27635 (15)0.5401 (3)0.30322 (19)0.0197 (6)
C70.19398 (17)0.6857 (3)0.5172 (2)0.0272 (7)
C80.11681 (17)0.6522 (4)0.5457 (2)0.0388 (8)
H8A0.11260.54510.55640.058*
H8B0.07480.68410.49420.058*
H8C0.11380.70610.60470.058*
C90.25655 (17)0.6366 (4)0.6014 (2)0.0332 (8)
H9A0.25370.52860.60970.050*
H9B0.24900.68670.66000.050*
H9C0.30700.66310.58850.050*
C100.1981 (2)0.8544 (3)0.5028 (2)0.0399 (9)
H10A0.24680.87970.48420.060*
H10B0.19490.90540.56270.060*
H10C0.15540.88600.45220.060*
C110.09420 (17)0.3034 (3)0.2554 (2)0.0365 (8)
C120.0664 (3)0.3407 (7)0.1489 (3)0.077 (2)0.834 (6)
H12A0.02750.26830.11990.115*0.834 (6)
H12B0.10990.33680.11610.115*0.834 (6)
H12C0.04420.44080.14280.115*0.834 (6)
C130.1347 (3)0.1529 (4)0.2641 (4)0.0600 (17)0.834 (6)
H13A0.09800.07500.23770.090*0.834 (6)
H13B0.15570.13180.33170.090*0.834 (6)
H13C0.17650.15520.22840.090*0.834 (6)
C140.0263 (2)0.2976 (5)0.3027 (4)0.0452 (13)0.834 (6)
H14A−0.00940.22090.27190.068*0.834 (6)
H14B0.00050.39440.29640.068*0.834 (6)
H14C0.04330.27350.37070.068*0.834 (6)
C12'0.1079 (13)0.210 (2)0.1736 (14)0.048 (7)0.166 (6)
H12D0.16210.21630.16940.073*0.166 (6)
H12E0.07610.24720.11390.073*0.166 (6)
H12F0.09440.10680.18390.073*0.166 (6)
C13'0.0927 (15)0.184 (2)0.3315 (15)0.074 (9)0.166 (6)
H13D0.13730.11850.33550.111*0.166 (6)
H13E0.04560.12480.31400.111*0.166 (6)
H13F0.09410.23130.39380.111*0.166 (6)
C14'0.0130 (7)0.361 (2)0.2415 (18)0.048 (7)0.166 (6)
H14D−0.00410.35890.30280.072*0.166 (6)
H14E−0.02080.29910.19480.072*0.166 (6)
H14F0.01140.46410.21800.072*0.166 (6)
C150.34660 (15)0.5559 (3)0.25896 (19)0.0225 (7)
H15A0.33740.50130.19740.027*
H15B0.35310.66230.24450.027*
C160.43888 (16)0.3562 (3)0.33031 (19)0.0203 (6)
C170.51327 (15)0.3219 (3)0.37876 (19)0.0205 (6)
H170.54820.40040.40040.025*
C180.53670 (16)0.1770 (3)0.39565 (19)0.0204 (6)
H180.58760.15650.42820.024*
C190.48608 (16)0.0590 (3)0.36514 (19)0.0202 (6)
C200.41230 (16)0.0918 (3)0.31703 (19)0.0220 (7)
H200.37740.01300.29600.026*
C210.38877 (16)0.2380 (3)0.29915 (18)0.0208 (6)
H210.33820.25810.26540.025*
C220.50943 (15)−0.0962 (3)0.38371 (18)0.0194 (6)
C230.61300 (17)−0.2598 (3)0.4479 (2)0.0245 (7)
H23A0.6072−0.32590.39120.029*
H23B0.5846−0.30370.49440.029*
C240.69625 (17)−0.2403 (3)0.4929 (2)0.0320 (8)
H24A0.7188−0.33740.51330.048*
H24B0.7009−0.17440.54860.048*
H24C0.7234−0.19640.44600.048*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0285 (12)0.0281 (11)0.0296 (12)−0.0076 (9)0.0102 (9)−0.0064 (9)
O20.0288 (12)0.0204 (11)0.0285 (11)−0.0036 (9)0.0072 (9)−0.0018 (9)
O30.0254 (11)0.0184 (10)0.0271 (11)0.0027 (8)0.0049 (9)0.0050 (8)
N10.0229 (13)0.0186 (13)0.0255 (13)0.0000 (10)0.0045 (11)−0.0029 (10)
C10.0232 (16)0.0138 (14)0.0229 (15)0.0011 (12)0.0001 (12)−0.0007 (12)
C20.0201 (16)0.0216 (15)0.0254 (15)0.0033 (12)0.0044 (12)0.0012 (12)
C30.0204 (16)0.0246 (16)0.0295 (17)0.0006 (12)0.0068 (13)0.0009 (13)
C40.0191 (16)0.0217 (15)0.0252 (16)0.0030 (12)−0.0009 (13)−0.0025 (12)
C50.0265 (17)0.0197 (15)0.0209 (15)0.0051 (12)0.0025 (13)−0.0006 (12)
C60.0225 (16)0.0176 (14)0.0189 (14)0.0036 (12)0.0035 (12)0.0029 (12)
C70.0275 (17)0.0290 (17)0.0277 (16)0.0003 (13)0.0114 (14)−0.0037 (13)
C80.0319 (19)0.051 (2)0.0372 (19)−0.0004 (16)0.0151 (16)−0.0107 (16)
C90.0332 (19)0.0406 (19)0.0275 (17)−0.0082 (15)0.0101 (14)−0.0066 (15)
C100.047 (2)0.0295 (18)0.047 (2)0.0008 (15)0.0194 (17)−0.0112 (16)
C110.0273 (18)0.0364 (19)0.044 (2)−0.0023 (15)0.0038 (16)−0.0094 (16)
C120.063 (3)0.113 (5)0.047 (3)−0.052 (3)−0.009 (2)−0.010 (3)
C130.045 (3)0.033 (2)0.106 (4)−0.014 (2)0.025 (3)−0.032 (3)
C140.028 (2)0.042 (3)0.068 (3)−0.0133 (19)0.016 (2)−0.016 (2)
C12'0.043 (10)0.047 (10)0.053 (10)−0.007 (8)0.004 (8)−0.026 (8)
C13'0.078 (12)0.063 (11)0.078 (12)−0.014 (9)0.007 (9)−0.005 (9)
C14'0.046 (10)0.050 (10)0.048 (10)−0.009 (8)0.007 (8)−0.012 (8)
C150.0259 (17)0.0199 (15)0.0218 (15)0.0045 (12)0.0047 (13)0.0009 (12)
C160.0259 (16)0.0195 (15)0.0174 (14)0.0004 (12)0.0090 (12)−0.0002 (12)
C170.0234 (16)0.0173 (14)0.0220 (15)−0.0040 (12)0.0075 (13)−0.0046 (12)
C180.0201 (15)0.0225 (15)0.0191 (14)0.0006 (12)0.0054 (12)−0.0018 (12)
C190.0218 (16)0.0220 (15)0.0181 (14)0.0009 (12)0.0072 (12)−0.0004 (12)
C200.0244 (16)0.0193 (15)0.0234 (15)−0.0033 (12)0.0075 (13)−0.0012 (12)
C210.0209 (15)0.0245 (16)0.0177 (15)0.0000 (12)0.0058 (12)−0.0026 (12)
C220.0193 (16)0.0228 (15)0.0176 (14)−0.0010 (13)0.0070 (12)−0.0016 (12)
C230.0359 (18)0.0181 (15)0.0212 (15)0.0056 (13)0.0095 (13)0.0042 (12)
C240.0344 (19)0.0292 (17)0.0323 (18)0.0076 (14)0.0065 (15)0.0098 (14)

Geometric parameters (Å, °)

O1—C11.376 (3)C12—H12A0.9800
O1—H1O0.8400C12—H12B0.9800
O2—C221.231 (3)C12—H12C0.9800
O3—C221.335 (3)C13—H13A0.9800
O3—C231.462 (3)C13—H13B0.9800
N1—C161.366 (3)C13—H13C0.9800
N1—C151.454 (3)C14—H14A0.9800
N1—H1N0.8800C14—H14B0.9800
C1—C61.397 (4)C14—H14C0.9800
C1—C21.407 (4)C12'—H12D0.9800
C2—C31.398 (4)C12'—H12E0.9800
C2—C71.534 (4)C12'—H12F0.9800
C3—C41.395 (4)C13'—H13D0.9800
C3—H30.9500C13'—H13E0.9800
C4—C51.391 (4)C13'—H13F0.9800
C4—C111.529 (4)C14'—H14D0.9800
C5—C61.384 (4)C14'—H14E0.9800
C5—H50.9500C14'—H14F0.9800
C6—C151.513 (4)C15—H15A0.9900
C7—C101.534 (4)C15—H15B0.9900
C7—C91.531 (4)C16—C171.400 (4)
C7—C81.536 (4)C16—C211.401 (4)
C8—H8A0.9800C17—C181.374 (4)
C8—H8B0.9800C17—H170.9500
C8—H8C0.9800C18—C191.403 (4)
C9—H9A0.9800C18—H180.9500
C9—H9B0.9800C19—C201.387 (4)
C9—H9C0.9800C19—C221.465 (4)
C10—H10A0.9800C20—C211.387 (4)
C10—H10B0.9800C20—H200.9500
C10—H10C0.9800C21—H210.9500
C11—C12'1.491 (9)C23—C241.503 (4)
C11—C141.495 (5)C23—H23A0.9900
C11—C14'1.511 (9)C23—H23B0.9900
C11—C131.526 (5)C24—H24A0.9800
C11—C13'1.531 (10)C24—H24B0.9800
C11—C121.535 (5)C24—H24C0.9800
C1—O1—H1O109.5H13A—C13—H13B109.5
C22—O3—C23117.5 (2)C11—C13—H13C109.5
C16—N1—C15125.5 (2)H13A—C13—H13C109.5
C16—N1—H1N117.2H13B—C13—H13C109.5
C15—N1—H1N117.2C11—C14—H14A109.5
O1—C1—C6121.0 (3)C11—C14—H14B109.5
O1—C1—C2117.8 (2)H14A—C14—H14B109.5
C6—C1—C2121.2 (2)C11—C14—H14C109.5
C3—C2—C1116.7 (3)H14A—C14—H14C109.5
C3—C2—C7121.1 (3)H14B—C14—H14C109.5
C1—C2—C7122.1 (2)C11—C12'—H12D109.5
C4—C3—C2123.9 (3)C11—C12'—H12E109.5
C4—C3—H3118.0H12D—C12'—H12E109.5
C2—C3—H3118.0C11—C12'—H12F109.5
C5—C4—C3116.5 (2)H12D—C12'—H12F109.5
C5—C4—C11120.2 (3)H12E—C12'—H12F109.5
C3—C4—C11123.2 (3)C11—C13'—H13D109.5
C6—C5—C4122.6 (3)C11—C13'—H13E109.5
C6—C5—H5118.7H13D—C13'—H13E109.5
C4—C5—H5118.7C11—C13'—H13F109.5
C5—C6—C1119.0 (3)H13D—C13'—H13F109.5
C5—C6—C15119.1 (2)H13E—C13'—H13F109.5
C1—C6—C15121.9 (2)C11—C14'—H14D109.5
C10—C7—C9110.0 (3)C11—C14'—H14E109.5
C10—C7—C8107.4 (3)H14D—C14'—H14E109.5
C9—C7—C8106.6 (2)C11—C14'—H14F109.5
C10—C7—C2110.6 (2)H14D—C14'—H14F109.5
C9—C7—C2110.0 (2)H14E—C14'—H14F109.5
C8—C7—C2112.2 (2)N1—C15—C6115.1 (2)
C7—C8—H8A109.5N1—C15—H15A108.5
C7—C8—H8B109.5C6—C15—H15A108.5
H8A—C8—H8B109.5N1—C15—H15B108.5
C7—C8—H8C109.5C6—C15—H15B108.5
H8A—C8—H8C109.5H15A—C15—H15B107.5
H8B—C8—H8C109.5N1—C16—C17119.0 (2)
C7—C9—H9A109.5N1—C16—C21123.0 (2)
C7—C9—H9B109.5C17—C16—C21118.0 (2)
H9A—C9—H9B109.5C18—C17—C16121.3 (2)
C7—C9—H9C109.5C18—C17—H17119.4
H9A—C9—H9C109.5C16—C17—H17119.4
H9B—C9—H9C109.5C17—C18—C19120.6 (3)
C7—C10—H10A109.5C17—C18—H18119.7
C7—C10—H10B109.5C19—C18—H18119.7
H10A—C10—H10B109.5C20—C19—C18118.6 (2)
C7—C10—H10C109.5C20—C19—C22119.9 (2)
H10A—C10—H10C109.5C18—C19—C22121.5 (2)
H10B—C10—H10C109.5C19—C20—C21120.9 (3)
C12'—C11—C14'113.0 (13)C19—C20—H20119.5
C14—C11—C13110.1 (3)C21—C20—H20119.5
C12'—C11—C13'100.8 (15)C20—C21—C16120.7 (3)
C14'—C11—C13'100.6 (13)C20—C21—H21119.7
C12'—C11—C4120.1 (9)C16—C21—H21119.7
C14—C11—C4112.8 (3)O2—C22—O3122.3 (2)
C14'—C11—C4111.9 (9)O2—C22—C19124.9 (2)
C13—C11—C4107.7 (3)O3—C22—C19112.8 (2)
C13'—C11—C4107.6 (10)O3—C23—C24105.7 (2)
C14—C11—C12108.7 (3)O3—C23—H23A110.6
C13—C11—C12109.1 (4)C24—C23—H23A110.6
C4—C11—C12108.3 (3)O3—C23—H23B110.6
C11—C12—H12A109.5C24—C23—H23B110.6
C11—C12—H12B109.5H23A—C23—H23B108.7
H12A—C12—H12B109.5C23—C24—H24A109.5
C11—C12—H12C109.5C23—C24—H24B109.5
H12A—C12—H12C109.5H24A—C24—H24B109.5
H12B—C12—H12C109.5C23—C24—H24C109.5
C11—C13—H13A109.5H24A—C24—H24C109.5
C11—C13—H13B109.5H24B—C24—H24C109.5
O1—C1—C2—C3−179.0 (2)C5—C4—C11—C1360.4 (4)
C6—C1—C2—C30.7 (4)C3—C4—C11—C13−115.5 (4)
O1—C1—C2—C7−1.2 (4)C5—C4—C11—C13'116.0 (12)
C6—C1—C2—C7178.5 (2)C3—C4—C11—C13'−59.9 (12)
C1—C2—C3—C4−0.5 (4)C5—C4—C11—C12−57.5 (4)
C7—C2—C3—C4−178.3 (3)C3—C4—C11—C12126.6 (4)
C2—C3—C4—C5−0.6 (4)C16—N1—C15—C677.4 (3)
C2—C3—C4—C11175.5 (3)C5—C6—C15—N1−113.9 (3)
C3—C4—C5—C61.5 (4)C1—C6—C15—N165.8 (3)
C11—C4—C5—C6−174.7 (3)C15—N1—C16—C17171.6 (2)
C4—C5—C6—C1−1.3 (4)C15—N1—C16—C21−10.2 (4)
C4—C5—C6—C15178.4 (2)N1—C16—C17—C18178.1 (3)
O1—C1—C6—C5179.8 (2)C21—C16—C17—C18−0.1 (4)
C2—C1—C6—C50.2 (4)C16—C17—C18—C19−0.5 (4)
O1—C1—C6—C150.1 (4)C17—C18—C19—C200.5 (4)
C2—C1—C6—C15−179.6 (2)C17—C18—C19—C22−179.0 (2)
C3—C2—C7—C10−123.6 (3)C18—C19—C20—C210.1 (4)
C1—C2—C7—C1058.7 (3)C22—C19—C20—C21179.6 (3)
C3—C2—C7—C9114.7 (3)C19—C20—C21—C16−0.7 (4)
C1—C2—C7—C9−63.1 (3)N1—C16—C21—C20−177.4 (3)
C3—C2—C7—C8−3.8 (4)C17—C16—C21—C200.7 (4)
C1—C2—C7—C8178.5 (3)C23—O3—C22—O2−4.9 (4)
C5—C4—C11—C12'1.7 (13)C23—O3—C22—C19175.4 (2)
C3—C4—C11—C12'−174.2 (12)C20—C19—C22—O2−7.5 (4)
C5—C4—C11—C14−177.9 (3)C18—C19—C22—O2172.0 (3)
C3—C4—C11—C146.2 (4)C20—C19—C22—O3172.2 (2)
C5—C4—C11—C14'−134.4 (11)C18—C19—C22—O3−8.3 (4)
C3—C4—C11—C14'49.7 (11)C22—O3—C23—C24−175.3 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1o···O2i0.842.132.909 (3)154
N1—H1n···O2i0.882.072.827 (3)143

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5371).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Shakir, R. M., Ariffin, A. & Ng, S. W. (2010). Acta Cryst. E66, o2915. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

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