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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2013 Jun 29;69(Pt 7):o1166. doi: 10.1107/S1600536813017157

4,4′-Di-tert-butyl-2,2′-[imidazolidine-1,3-diylbis(methyl­ene)]diphenol

Augusto Rivera a,*, Luz Stella Nerio a, Michael Bolte b
PMCID: PMC3770425  PMID: 24046710

Abstract

In the title compound, C25H36N2O2, the two tert-butyl-substituted benzene rings are inclined at an angle of 53.5 (3)° to one another. The imidazolidine ring has an envelope conformation with with one of the C atoms of the ethylene fragment as the flap. The structure displays two intra­molecular O—H⋯N hydrogen bonds that generate S(6) ring motifs. The crystal studied was a non-merohedral twin with a fractional contribution of 0.281(6) for the minor domain.

Related literature  

For related structures, see: Rivera et al. (2011 ▶, 2012a ▶,b ▶); Rivera, Nerio, Ríos-Motta, Fejfarová et al. (2012 ▶). For the use of the 2,2′-[imidazolidine-1,3-diylbis(methyl­ene)]diphenol system as a ligand in the synthesis of a variety of coordination compounds, see: Kober et al. (2012 ▶); Xu et al. (2007 ▶); Zhang et al. (2009 ▶). For the original synthesis of the title compound, see: Rivera et al. (1993 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).graphic file with name e-69-o1166-scheme1.jpg

Experimental  

Crystal data  

  • C25H36N2O2

  • M r = 396.56

  • Monoclinic, Inline graphic

  • a = 21.0879 (16) Å

  • b = 6.2110 (4) Å

  • c = 17.9086 (16) Å

  • β = 109.168 (6)°

  • V = 2215.6 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 173 K

  • 0.24 × 0.22 × 0.19 mm

Data collection  

  • Stoe IPDS II two-circle diffractometer

  • 22835 measured reflections

  • 3909 independent reflections

  • 3131 reflections with I > 2σ(I)

  • R int = 0.101

Refinement  

  • R[F 2 > 2σ(F 2)] = 0.119

  • wR(F 2) = 0.324

  • S = 1.13

  • 3909 reflections

  • 272 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.42 e Å−3

  • Δρmin = −0.39 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: XRED-32 (Stoe & Cie, 2001 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813017157/sj5337sup1.cif

e-69-o1166-sup1.cif (191.5KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813017157/sj5337Isup2.hkl

e-69-o1166-Isup2.hkl (214.5KB, hkl)
Click here for additional data file. (8.5KB, cml)

Supplementary material file. DOI: 10.1107/S1600536813017157/sj5337Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1⋯N1 1.00 (10) 1.70 (10) 2.655 (7) 157 (8)
O2—H2⋯N2 0.95 (8) 1.83 (8) 2.656 (7) 144 (7)
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Acknowledgments

The authors acknowledge the Dirección de Investigaciones, Sede Bogotá (DIB) de la Universidad Nacional de Colombia, for financial support of this work. LSN thanks COLCIENCIAS for a fellowship.

supplementary crystallographic information

Comment

2,2'-[imidazolidine-1,3-diylbis(methylene)]diphenol system has been used as ligand in the synthesis of a variety of coordination compounds, with potential applications in homogeneous catalysis (Kober et al., 2012, Xu et al., 2007, Zhang et al., 2009). The molecular structure and atom-numbering scheme for (I) are shown in Fig. 1. The imidazolidine ring adopts an envelope conformation, with C3 as the flap. The dihedral angle between aromatic rings is 53.5 (3)°. Its X-ray structure confirms the presence of two intramolecular hydrogen bonds between the phenolic hydroxyl groups and the imidazolidine nitrogen atoms with S(6) graph-set motifs (Bernstein et al., 1995) (Table 1).

Experimental

For the original synthesis of the title compound, see: Rivera et al. (1993). Single crystals suitable for X-ray diffraction were obtained from a mixture chloroform:methanol (1:1), by slow evaporation over 5 days at room temperature.

Refinement

H atoms bonded to C were positioned geometrically, with C–H = 0.95–0.99 Å and constrained to ride on their parent atom, with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for other H atoms. The crystal was a non-merohedral twin with a fractional contribution of 0.281 (6) for the minor domain. The twin law is (1 0 0.773/0 - 1 0/0 0 - 1). As a result of this twinning, the figures of merit are rather high. Nevertheless, the H atoms bonded to O could be located in a difference map and they could be freely refined.

Figures

Fig. 1.

Fig. 1.

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The molecular structure of the title compound, displacement ellipsoids are drawn at the 50% probability level. Intramolecular hydrogen bonds are drawn as dashed lines.

Crystal data

C25H36N2O2 F(000) = 864
Mr = 396.56 Dx = 1.189 Mg m−3
Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å
a = 21.0879 (16) Å Cell parameters from 20905 reflections
b = 6.2110 (4) Å θ = 2.1–26.0°
c = 17.9086 (16) Å µ = 0.08 mm−1
β = 109.168 (6)° T = 173 K
V = 2215.6 (3) Å3 Block, colourless
Z = 4 0.24 × 0.22 × 0.19 mm
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Data collection

Stoe IPDS II two-circle diffractometer Rint = 0.101
Radiation source: Genix 3D IµS microfocus X-ray source θmax = 25.0°, θmin = 2.1°
ω scans h = −25→24
22835 measured reflections k = −7→7
3909 independent reflections l = −18→21
3131 reflections with I > 2σ(I)
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Refinement

Refinement on F2 Hydrogen site location: mixed
Least-squares matrix: full H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.119 w = 1/[σ2(Fo2) + (0.0705P)2 + 10.9502P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.324 (Δ/σ)max < 0.001
S = 1.13 Δρmax = 0.42 e Å−3
3909 reflections Δρmin = −0.39 e Å−3
272 parameters Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints Extinction coefficient: 0.037 (4)
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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. Refined as a 2-component twin.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
O1 0.4712 (2) 0.0117 (8) 0.5876 (3) 0.0455 (12)
H1 0.500 (5) 0.122 (16) 0.624 (6) 0.09 (3)*
O2 0.6663 (2) 0.9590 (8) 0.7246 (3) 0.0455 (12)
H2 0.635 (4) 0.845 (13) 0.716 (5) 0.06 (2)*
N1 0.5256 (3) 0.3720 (9) 0.6606 (3) 0.0385 (13)
N2 0.6261 (3) 0.5545 (8) 0.7268 (3) 0.0368 (13)
C1 0.5734 (3) 0.4179 (13) 0.7397 (4) 0.0489 (18)
H1A 0.5929 0.2827 0.7669 0.059*
H1B 0.5508 0.4945 0.7724 0.059*
C2 0.5537 (3) 0.4692 (12) 0.6021 (4) 0.0433 (16)
H2A 0.5346 0.6139 0.5854 0.052*
H2B 0.5453 0.3765 0.5549 0.052*
C3 0.6280 (3) 0.4820 (11) 0.6489 (4) 0.0369 (14)
H3A 0.6501 0.3398 0.6525 0.044*
H3B 0.6513 0.5875 0.6256 0.044*
C4 0.4565 (3) 0.4390 (11) 0.6528 (4) 0.0419 (16)
H4A 0.4524 0.5964 0.6437 0.050*
H4B 0.4483 0.4089 0.7031 0.050*
C5 0.6896 (3) 0.5301 (11) 0.7933 (4) 0.0394 (15)
H5A 0.7046 0.3785 0.7960 0.047*
H5B 0.6813 0.5639 0.8434 0.047*
C11 0.4026 (3) 0.3260 (10) 0.5857 (4) 0.0364 (14)
C12 0.4124 (3) 0.1211 (11) 0.5592 (4) 0.0407 (15)
C13 0.3586 (4) 0.0247 (11) 0.5019 (4) 0.0492 (18)
H13 0.3648 −0.1113 0.4810 0.059*
C14 0.2970 (4) 0.1210 (11) 0.4750 (4) 0.0449 (16)
H14 0.2617 0.0508 0.4354 0.054*
C15 0.2846 (3) 0.3197 (10) 0.5040 (4) 0.0399 (15)
C16 0.3396 (3) 0.4209 (11) 0.5576 (4) 0.0421 (16)
H16 0.3339 0.5608 0.5758 0.050*
C17 0.2157 (3) 0.4268 (12) 0.4738 (4) 0.0420 (16)
C18 0.2078 (4) 0.5451 (13) 0.3962 (4) 0.0518 (19)
H18A 0.2141 0.4431 0.3574 0.078*
H18B 0.2415 0.6596 0.4057 0.078*
H18C 0.1628 0.6081 0.3758 0.078*
C19 0.2058 (4) 0.5876 (14) 0.5326 (4) 0.055 (2)
H19A 0.2104 0.5144 0.5825 0.082*
H19B 0.1609 0.6510 0.5114 0.082*
H19C 0.2396 0.7015 0.5417 0.082*
C20 0.1589 (4) 0.2555 (15) 0.4574 (6) 0.066 (2)
H20A 0.1629 0.1777 0.5063 0.099*
H20B 0.1630 0.1537 0.4174 0.099*
H20C 0.1152 0.3272 0.4381 0.099*
C21 0.7443 (3) 0.6742 (10) 0.7855 (4) 0.0363 (14)
C22 0.7299 (3) 0.8793 (10) 0.7516 (4) 0.0403 (15)
C23 0.7822 (3) 1.0074 (11) 0.7463 (4) 0.0434 (16)
H23 0.7731 1.1453 0.7222 0.052*
C24 0.8475 (3) 0.9344 (11) 0.7760 (4) 0.0434 (16)
H24 0.8825 1.0241 0.7715 0.052*
C25 0.8639 (3) 0.7346 (11) 0.8122 (4) 0.0422 (16)
C26 0.8101 (3) 0.6077 (10) 0.8153 (4) 0.0366 (14)
H26 0.8194 0.4693 0.8390 0.044*
C27 0.9369 (3) 0.6602 (12) 0.8458 (5) 0.0506 (18)
C28 0.9627 (4) 0.613 (2) 0.7759 (6) 0.090 (4)
H28A 0.9588 0.7433 0.7438 0.135*
H28B 0.9359 0.4975 0.7432 0.135*
H28C 1.0099 0.5687 0.7964 0.135*
C29 0.9436 (4) 0.4555 (14) 0.8947 (6) 0.069 (2)
H29A 0.9159 0.3417 0.8619 0.103*
H29B 0.9286 0.4836 0.9401 0.103*
H29C 0.9907 0.4094 0.9134 0.103*
C30 0.9809 (4) 0.8335 (14) 0.8977 (6) 0.071 (3)
H30A 0.9768 0.9669 0.8672 0.106*
H30B 1.0278 0.7858 0.9156 0.106*
H30C 0.9665 0.8595 0.9436 0.106*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O1 0.044 (3) 0.040 (3) 0.055 (3) 0.004 (2) 0.020 (2) −0.007 (2)
O2 0.039 (3) 0.036 (3) 0.055 (3) 0.004 (2) 0.007 (2) 0.006 (2)
N1 0.034 (3) 0.046 (3) 0.039 (3) −0.001 (2) 0.017 (2) 0.001 (2)
N2 0.033 (3) 0.039 (3) 0.037 (3) −0.003 (2) 0.011 (2) −0.003 (2)
C1 0.039 (4) 0.055 (4) 0.053 (4) −0.012 (3) 0.014 (3) 0.000 (4)
C2 0.039 (4) 0.047 (4) 0.041 (4) 0.003 (3) 0.010 (3) 0.001 (3)
C3 0.039 (3) 0.038 (3) 0.033 (3) −0.004 (3) 0.011 (3) −0.004 (3)
C4 0.036 (3) 0.042 (4) 0.051 (4) −0.001 (3) 0.020 (3) −0.008 (3)
C5 0.036 (3) 0.044 (4) 0.036 (3) 0.001 (3) 0.009 (3) 0.002 (3)
C11 0.037 (3) 0.032 (3) 0.041 (4) −0.004 (3) 0.015 (3) −0.003 (3)
C12 0.047 (4) 0.039 (4) 0.039 (3) 0.001 (3) 0.017 (3) 0.005 (3)
C13 0.060 (4) 0.032 (3) 0.052 (4) −0.003 (3) 0.013 (4) −0.005 (3)
C14 0.051 (4) 0.041 (4) 0.042 (4) −0.008 (3) 0.014 (3) −0.006 (3)
C15 0.040 (3) 0.038 (3) 0.042 (4) −0.004 (3) 0.013 (3) 0.003 (3)
C16 0.038 (3) 0.036 (3) 0.050 (4) −0.001 (3) 0.012 (3) −0.001 (3)
C17 0.035 (3) 0.051 (4) 0.041 (4) −0.001 (3) 0.014 (3) 0.006 (3)
C18 0.048 (4) 0.065 (5) 0.039 (4) 0.001 (4) 0.010 (3) 0.005 (3)
C19 0.048 (4) 0.068 (5) 0.046 (4) 0.013 (4) 0.012 (3) 0.000 (4)
C20 0.040 (4) 0.072 (5) 0.081 (6) −0.012 (4) 0.011 (4) 0.006 (5)
C21 0.041 (3) 0.035 (3) 0.030 (3) −0.004 (3) 0.009 (3) −0.003 (3)
C22 0.042 (4) 0.035 (3) 0.044 (4) 0.000 (3) 0.013 (3) −0.003 (3)
C23 0.055 (4) 0.036 (3) 0.037 (3) −0.007 (3) 0.013 (3) 0.005 (3)
C24 0.042 (4) 0.047 (4) 0.043 (4) −0.013 (3) 0.016 (3) −0.003 (3)
C25 0.042 (4) 0.042 (4) 0.040 (4) −0.005 (3) 0.010 (3) −0.006 (3)
C26 0.036 (3) 0.036 (3) 0.035 (3) 0.001 (3) 0.008 (3) −0.003 (3)
C27 0.040 (4) 0.055 (4) 0.052 (4) −0.003 (3) 0.010 (3) −0.007 (4)
C28 0.049 (5) 0.135 (10) 0.089 (7) 0.009 (6) 0.027 (5) −0.027 (7)
C29 0.045 (4) 0.056 (5) 0.094 (7) 0.002 (4) 0.007 (4) 0.000 (5)
C30 0.055 (5) 0.055 (5) 0.085 (6) −0.010 (4) −0.001 (4) −0.011 (5)
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Geometric parameters (Å, º)

O1—C12 1.357 (8) C17—C18 1.533 (10)
O1—H1 1.00 (10) C17—C20 1.556 (10)
O2—C22 1.360 (8) C18—H18A 0.9800
O2—H2 0.95 (8) C18—H18B 0.9800
N1—C1 1.473 (9) C18—H18C 0.9800
N1—C4 1.478 (8) C19—H19A 0.9800
N1—C2 1.490 (9) C19—H19B 0.9800
N2—C1 1.476 (8) C19—H19C 0.9800
N2—C5 1.479 (8) C20—H20A 0.9800
N2—C3 1.479 (8) C20—H20B 0.9800
C1—H1A 0.9900 C20—H20C 0.9800
C1—H1B 0.9900 C21—C26 1.377 (9)
C2—C3 1.517 (9) C21—C22 1.401 (9)
C2—H2A 0.9900 C22—C23 1.389 (9)
C2—H2B 0.9900 C23—C24 1.378 (10)
C3—H3A 0.9900 C23—H23 0.9500
C3—H3B 0.9900 C24—C25 1.391 (10)
C4—C11 1.526 (9) C24—H24 0.9500
C4—H4A 0.9900 C25—C26 1.397 (9)
C4—H4B 0.9900 C25—C27 1.529 (9)
C5—C21 1.503 (9) C26—H26 0.9500
C5—H5A 0.9900 C27—C30 1.522 (10)
C5—H5B 0.9900 C27—C29 1.523 (12)
C11—C16 1.388 (9) C27—C28 1.549 (12)
C11—C12 1.397 (9) C28—H28A 0.9800
C12—C13 1.392 (10) C28—H28B 0.9800
C13—C14 1.365 (10) C28—H28C 0.9800
C13—H13 0.9500 C29—H29A 0.9800
C14—C15 1.397 (9) C29—H29B 0.9800
C14—H14 0.9500 C29—H29C 0.9800
C15—C16 1.390 (9) C30—H30A 0.9800
C15—C17 1.526 (9) C30—H30B 0.9800
C16—H16 0.9500 C30—H30C 0.9800
C17—C19 1.514 (10)
C12—O1—H1 101 (5) C18—C17—C20 108.0 (6)
C22—O2—H2 110 (5) C17—C18—H18A 109.5
C1—N1—C4 112.3 (5) C17—C18—H18B 109.5
C1—N1—C2 107.0 (5) H18A—C18—H18B 109.5
C4—N1—C2 115.3 (5) C17—C18—H18C 109.5
C1—N2—C5 110.1 (5) H18A—C18—H18C 109.5
C1—N2—C3 103.2 (5) H18B—C18—H18C 109.5
C5—N2—C3 115.6 (5) C17—C19—H19A 109.5
N1—C1—N2 105.8 (5) C17—C19—H19B 109.5
N1—C1—H1A 110.6 H19A—C19—H19B 109.5
N2—C1—H1A 110.6 C17—C19—H19C 109.5
N1—C1—H1B 110.6 H19A—C19—H19C 109.5
N2—C1—H1B 110.6 H19B—C19—H19C 109.5
H1A—C1—H1B 108.7 C17—C20—H20A 109.5
N1—C2—C3 102.2 (5) C17—C20—H20B 109.5
N1—C2—H2A 111.3 H20A—C20—H20B 109.5
C3—C2—H2A 111.3 C17—C20—H20C 109.5
N1—C2—H2B 111.3 H20A—C20—H20C 109.5
C3—C2—H2B 111.3 H20B—C20—H20C 109.5
H2A—C2—H2B 109.2 C26—C21—C22 119.3 (6)
N2—C3—C2 101.1 (5) C26—C21—C5 119.5 (6)
N2—C3—H3A 111.5 C22—C21—C5 121.2 (6)
C2—C3—H3A 111.5 O2—C22—C23 118.7 (6)
N2—C3—H3B 111.5 O2—C22—C21 122.2 (6)
C2—C3—H3B 111.5 C23—C22—C21 119.1 (6)
H3A—C3—H3B 109.4 C24—C23—C22 120.0 (6)
N1—C4—C11 113.6 (5) C24—C23—H23 120.0
N1—C4—H4A 108.8 C22—C23—H23 120.0
C11—C4—H4A 108.8 C23—C24—C25 122.5 (6)
N1—C4—H4B 108.8 C23—C24—H24 118.8
C11—C4—H4B 108.8 C25—C24—H24 118.8
H4A—C4—H4B 107.7 C24—C25—C26 116.2 (6)
N2—C5—C21 112.5 (5) C24—C25—C27 121.2 (6)
N2—C5—H5A 109.1 C26—C25—C27 122.6 (6)
C21—C5—H5A 109.1 C21—C26—C25 122.9 (6)
N2—C5—H5B 109.1 C21—C26—H26 118.6
C21—C5—H5B 109.1 C25—C26—H26 118.6
H5A—C5—H5B 107.8 C30—C27—C29 108.5 (7)
C16—C11—C12 119.6 (6) C30—C27—C25 111.1 (6)
C16—C11—C4 117.8 (6) C29—C27—C25 111.7 (6)
C12—C11—C4 122.1 (6) C30—C27—C28 108.7 (7)
O1—C12—C13 119.0 (6) C29—C27—C28 108.4 (8)
O1—C12—C11 123.2 (6) C25—C27—C28 108.4 (6)
C13—C12—C11 117.8 (6) C27—C28—H28A 109.5
C14—C13—C12 121.5 (7) C27—C28—H28B 109.5
C14—C13—H13 119.2 H28A—C28—H28B 109.5
C12—C13—H13 119.2 C27—C28—H28C 109.5
C13—C14—C15 121.9 (7) H28A—C28—H28C 109.5
C13—C14—H14 119.0 H28B—C28—H28C 109.5
C15—C14—H14 119.0 C27—C29—H29A 109.5
C16—C15—C14 116.1 (6) C27—C29—H29B 109.5
C16—C15—C17 121.9 (6) H29A—C29—H29B 109.5
C14—C15—C17 121.8 (6) C27—C29—H29C 109.5
C11—C16—C15 122.8 (6) H29A—C29—H29C 109.5
C11—C16—H16 118.6 H29B—C29—H29C 109.5
C15—C16—H16 118.6 C27—C30—H30A 109.5
C19—C17—C15 112.0 (6) C27—C30—H30B 109.5
C19—C17—C18 108.4 (6) H30A—C30—H30B 109.5
C15—C17—C18 109.7 (6) C27—C30—H30C 109.5
C19—C17—C20 108.0 (6) H30A—C30—H30C 109.5
C15—C17—C20 110.6 (6) H30B—C30—H30C 109.5
C4—N1—C1—N2 −123.4 (6) C16—C15—C17—C19 −26.9 (9)
C2—N1—C1—N2 4.0 (7) C14—C15—C17—C19 157.8 (7)
C5—N2—C1—N1 −154.4 (5) C16—C15—C17—C18 93.5 (8)
C3—N2—C1—N1 −30.5 (7) C14—C15—C17—C18 −81.8 (8)
C1—N1—C2—C3 23.1 (7) C16—C15—C17—C20 −147.5 (7)
C4—N1—C2—C3 148.8 (5) C14—C15—C17—C20 37.2 (9)
C1—N2—C3—C2 44.4 (6) N2—C5—C21—C26 −148.4 (6)
C5—N2—C3—C2 164.6 (5) N2—C5—C21—C22 34.6 (8)
N1—C2—C3—N2 −41.3 (6) C26—C21—C22—O2 −176.7 (6)
C1—N1—C4—C11 −159.1 (6) C5—C21—C22—O2 0.3 (10)
C2—N1—C4—C11 77.9 (7) C26—C21—C22—C23 2.4 (9)
C1—N2—C5—C21 −177.0 (6) C5—C21—C22—C23 179.4 (6)
C3—N2—C5—C21 66.5 (7) O2—C22—C23—C24 177.5 (6)
N1—C4—C11—C16 −160.5 (6) C21—C22—C23—C24 −1.6 (10)
N1—C4—C11—C12 27.4 (9) C22—C23—C24—C25 −0.4 (11)
C16—C11—C12—O1 −175.5 (6) C23—C24—C25—C26 1.6 (10)
C4—C11—C12—O1 −3.6 (10) C23—C24—C25—C27 −178.9 (7)
C16—C11—C12—C13 3.2 (10) C22—C21—C26—C25 −1.2 (10)
C4—C11—C12—C13 175.2 (6) C5—C21—C26—C25 −178.2 (6)
O1—C12—C13—C14 175.6 (7) C24—C25—C26—C21 −0.8 (10)
C11—C12—C13—C14 −3.2 (11) C27—C25—C26—C21 179.7 (6)
C12—C13—C14—C15 −0.7 (11) C24—C25—C27—C30 48.9 (10)
C13—C14—C15—C16 4.5 (10) C26—C25—C27—C30 −131.5 (8)
C13—C14—C15—C17 −180.0 (7) C24—C25—C27—C29 170.2 (7)
C12—C11—C16—C15 0.7 (10) C26—C25—C27—C29 −10.3 (10)
C4—C11—C16—C15 −171.6 (6) C24—C25—C27—C28 −70.4 (9)
C14—C15—C16—C11 −4.4 (10) C26—C25—C27—C28 109.1 (9)
C17—C15—C16—C11 180.0 (6)
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Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A
O1—H1···N1 1.00 (10) 1.70 (10) 2.655 (7) 157 (8)
O2—H2···N2 0.95 (8) 1.83 (8) 2.656 (7) 144 (7)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5337).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813017157/sj5337sup1.cif

e-69-o1166-sup1.cif (191.5KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813017157/sj5337Isup2.hkl

e-69-o1166-Isup2.hkl (214.5KB, hkl)
Click here for additional data file. (8.5KB, cml)

Supplementary material file. DOI: 10.1107/S1600536813017157/sj5337Isup3.cml

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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