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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2010 May 8;66(Pt 6):o1256–o1257. doi: 10.1107/S1600536810015291

N,N′-Bis[(2-hydroxy­phen­yl)(phen­yl)methyl­idene]propane-1,2-diamine

Robert S Black a, David G Billing a,*, Agata Bartyzel a,‡, Ewa M Cukrowska a
PMCID: PMC2979517  PMID: 21579360

Abstract

In the the title compound, C29H26N2O2, two strong intra­molecular O—H⋯N hydrogen bonds involving the hydr­oxy and imine groups generate S(6) ring motifs. The dihedral angles between the pairs of terminal benzene rings are 89.8 (2) and 87.8 (2)°.

Related literature

For related compounds and further synthetic details, see: Schilf et al. (2007 ▶). For intra­molecular hydrogen bonds in this type of compound, see: Fernández-G et al. (2001 ▶); Kabak (2003 ▶); Wojciechowski et al. (2001 ▶); Dey et al. (2001); Koşar et al. (2004 ▶); Lu et al. (2008 ▶); Qiu & Zhao (2008 ▶); Montazerozohori et al. (2009 ▶); Corden et al. (1996 ▶); Black et al. (2010 ▶); Dey et al. (2001 ▶).graphic file with name e-66-o1256-scheme1.jpg

Experimental

Crystal data

  • C29H26N2O2

  • M r = 434.52

  • Monoclinic, Inline graphic

  • a = 18.1766 (8) Å

  • b = 7.9808 (4) Å

  • c = 16.0347 (8) Å

  • β = 92.703 (2)°

  • V = 2323.47 (19) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 296 K

  • 0.62 × 0.38 × 0.24 mm

Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: integration (XPREP; Bruker, 1999 ▶) T min = 0.918, T max = 1.000

  • 22291 measured reflections

  • 3001 independent reflections

  • 2724 reflections with I > 2σ(I)

  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034

  • wR(F 2) = 0.087

  • S = 1.05

  • 3001 reflections

  • 301 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-NT (Bruker, 2005 ▶); data reduction: SAINT-NT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810015291/hb5392sup1.cif

e-66-o1256-sup1.cif (22.5KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015291/hb5392Isup2.hkl

e-66-o1256-Isup2.hkl (144.3KB, hkl)

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

Table 1. Selected torsion angles (°).

C1—C6—C7—C8 89.8 (2)
C17—C22—C23—C24 87.8 (2)
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Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1—H1A⋯N1 0.82 1.84 2.573 (2) 147
O2—H2A⋯N2 0.82 1.83 2.553 (2) 147
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Acknowledgments

The University of the Witwatersrand and the National Research Foundation (GUN 2069064) are thanked for providing the infrastructure and for the award of a research grant required to carry out this work.

supplementary crystallographic information

Comment

The molecular structure of the title compound form two strong intermolecular hydrogen bonds O—H···N involving the hydroxyl and the imine groups, forming S(6) ring motifs which are common to this type of compound (Schilf et al., 2007) and (Fernández-G et al., 2001), and also seen in the work completed by (Kabak et al., 2003), (Wojciechowski et al., 2001), (Dey et al., 2001), (Koşar, et al., 2004), (Lu, et al., 2008) (Qiu & Zhao, 2008), (Montazerozohori et al., 2009), (Corden et al., 1996) and (Black et al., 2010). This causes the dihedral angles between the adjacent phenyl rings and phenyl containing plains to be (C1—C6—C7—C8) 89.8 (2)° and (C17—C22—C23—C24) 87.8 (2)° respectively. These dihedral angles are comparable to (Corden et al., 1996) and (Black et al., 2010). The stereogenic centre on the methyl substituted carbon C15 allows the system to pack in the noncentrosymmetric space group C2. The remaining weak interactions in the crystals form unexceptional σ-π interactions.

Experimental

A mixture of 0.01 mol (2.00 g) of 2-hydroxybenzophenone and 0.005 mole (0.42 ml) of 1,2-propanediamine in 40 ml of methanol was refluxed for 7 h. The excess of solvent (ca. 30 ml) was then evaporated. After cooling to 277 K, a yellow solid was produced. The polycrystalline product was collected by filtration, washed with methanol and dried a yield 54% was obtained. Recrystalization from an ethanol solution yielded yellow blocks of (I). Elemental analysis: C% 79.67 H% 5.99 N% 6.03.

Refinement

The absolute structure of (I) is indeterminate based on the present refinement. All H atoms were refined using a riding model, with a C—H distance of 0.96, for Ar—H a distance of 0.93 Å and for O—H a distance of 0.82 Å, and Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O). The highest residual peak was 0.742 Å from atom C6 with a ρ = 0.20 e Å-3.

Figures

Fig. 1.

Fig. 1.

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The molecular structure of (I) drawn at the 30% probability displacement ellipsoids. Hydrogens bonds are shown as dashed lines.

Crystal data

C29H26N2O2 F(000) = 920
Mr = 434.52 Dx = 1.242 Mg m−3
Monoclinic, C2 Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y Cell parameters from 9931 reflections
a = 18.1766 (8) Å θ = 2.2–28.3°
b = 7.9808 (4) Å µ = 0.08 mm−1
c = 16.0347 (8) Å T = 296 K
β = 92.703 (2)° Block, yellow
V = 2323.47 (19) Å3 0.62 × 0.38 × 0.24 mm
Z = 4
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Data collection

Bruker APEXII CCD diffractometer 3001 independent reflections
Radiation source: sealed tube 2724 reflections with I > 2σ(I)
graphite Rint = 0.026
φ and ω scans θmax = 28°, θmin = 1.3°
Absorption correction: integration (XPREP; Bruker, 1999) h = −23→24
Tmin = 0.918, Tmax = 1.000 k = −10→10
22291 measured reflections l = −21→20
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Refinement

Refinement on F2 1 restraint
Least-squares matrix: full H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.034 w = 1/[σ2(Fo2) + (0.0448P)2 + 0.6417P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.087 (Δ/σ)max = 0.001
S = 1.05 Δρmax = 0.20 e Å−3
3001 reflections Δρmin = −0.18 e Å−3
301 parameters
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Special details

Experimental. Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 1999)
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
C1 0.17117 (10) 0.8773 (3) 0.19104 (12) 0.0380 (4)
H1 0.1576 0.8561 0.2453 0.046*
C2 0.23795 (11) 0.9528 (3) 0.17780 (14) 0.0452 (5)
H2 0.2699 0.9792 0.2229 0.054*
C3 0.25725 (11) 0.9890 (3) 0.09795 (15) 0.0500 (5)
H3 0.302 1.0411 0.0891 0.06*
C4 0.21054 (12) 0.9484 (3) 0.03135 (14) 0.0536 (5)
H4 0.2237 0.974 −0.0225 0.064*
C5 0.14368 (11) 0.8693 (3) 0.04351 (12) 0.0432 (5)
H5 0.1124 0.8412 −0.0019 0.052*
C6 0.12418 (9) 0.8328 (2) 0.12419 (11) 0.0318 (4)
C7 0.05455 (9) 0.7387 (2) 0.14143 (10) 0.0308 (4)
C8 −0.01204 (10) 0.8365 (2) 0.15614 (11) 0.0317 (4)
C9 −0.01477 (11) 1.0091 (2) 0.14096 (13) 0.0398 (4)
H9 0.0267 1.0624 0.1219 0.048*
C10 −0.07704 (12) 1.1025 (3) 0.15342 (13) 0.0478 (5)
H10 −0.0777 1.2167 0.142 0.057*
C11 −0.13872 (12) 1.0242 (3) 0.18322 (14) 0.0487 (5)
H11 −0.1808 1.0867 0.1924 0.058*
C12 −0.13812 (11) 0.8549 (3) 0.19929 (13) 0.0445 (5)
H12 −0.1796 0.8042 0.2199 0.053*
C13 −0.07625 (10) 0.7587 (3) 0.18505 (12) 0.0372 (4)
C14 0.09851 (12) 0.3771 (3) 0.04854 (12) 0.0445 (5)
H14A 0.0548 0.3114 0.0545 0.067*
H14B 0.139 0.3044 0.0374 0.067*
H14C 0.0907 0.4544 0.0031 0.067*
C15 0.11599 (10) 0.4740 (2) 0.12901 (11) 0.0330 (4)
H15 0.1592 0.5453 0.1221 0.04*
C16 0.13115 (11) 0.3541 (2) 0.20186 (11) 0.0364 (4)
H16A 0.0869 0.2909 0.2124 0.044*
H16B 0.1695 0.2755 0.1882 0.044*
C17 −0.00368 (11) 0.3145 (3) 0.35288 (13) 0.0447 (5)
H17 −0.0215 0.4205 0.3389 0.054*
C18 −0.05238 (12) 0.1829 (4) 0.36563 (14) 0.0602 (7)
H18 −0.1029 0.2012 0.3604 0.072*
C19 −0.02579 (16) 0.0266 (4) 0.38587 (16) 0.0640 (7)
H19 −0.0585 −0.0607 0.3944 0.077*
C20 0.04851 (16) −0.0019 (3) 0.39361 (17) 0.0639 (7)
H20 0.066 −0.1085 0.4071 0.077*
C21 0.09762 (13) 0.1270 (3) 0.38147 (14) 0.0477 (5)
H21 0.148 0.1073 0.3869 0.057*
C22 0.07149 (10) 0.2860 (2) 0.36114 (11) 0.0331 (4)
C23 0.12560 (9) 0.4238 (2) 0.34679 (11) 0.0307 (3)
C24 0.14855 (9) 0.5331 (2) 0.41770 (11) 0.0304 (3)
C25 0.11331 (10) 0.5252 (2) 0.49331 (12) 0.0368 (4)
H25 0.0749 0.4495 0.4988 0.044*
C26 0.13414 (11) 0.6270 (3) 0.56007 (13) 0.0437 (5)
H26 0.1102 0.6195 0.6099 0.052*
C27 0.19109 (12) 0.7405 (3) 0.55188 (14) 0.0477 (5)
H27 0.2049 0.8105 0.5963 0.057*
C28 0.22735 (11) 0.7505 (3) 0.47865 (13) 0.0461 (5)
H28 0.2658 0.8264 0.4741 0.055*
C29 0.20693 (9) 0.6482 (2) 0.41146 (11) 0.0355 (4)
N1 0.05252 (8) 0.57835 (19) 0.14636 (9) 0.0338 (3)
N2 0.15442 (8) 0.44924 (19) 0.27629 (9) 0.0348 (3)
O1 −0.07848 (8) 0.59298 (19) 0.20016 (11) 0.0509 (4)
H1A −0.0408 0.5489 0.1844 0.076*
O2 0.24508 (8) 0.6613 (2) 0.34177 (8) 0.0487 (4)
H2A 0.2264 0.6006 0.3053 0.073*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
C1 0.0384 (10) 0.0346 (9) 0.0407 (9) −0.0049 (8) 0.0003 (8) −0.0001 (8)
C2 0.0365 (10) 0.0390 (10) 0.0591 (12) −0.0070 (8) −0.0073 (8) −0.0052 (9)
C3 0.0296 (10) 0.0468 (12) 0.0742 (14) −0.0096 (9) 0.0104 (9) −0.0005 (11)
C4 0.0464 (11) 0.0669 (14) 0.0487 (11) −0.0111 (11) 0.0144 (9) 0.0084 (11)
C5 0.0386 (10) 0.0536 (12) 0.0374 (9) −0.0087 (9) 0.0009 (8) 0.0026 (9)
C6 0.0301 (9) 0.0270 (8) 0.0383 (9) −0.0033 (7) 0.0021 (7) 0.0017 (7)
C7 0.0299 (8) 0.0341 (9) 0.0280 (8) −0.0069 (7) −0.0017 (6) 0.0013 (6)
C8 0.0303 (9) 0.0335 (9) 0.0311 (8) −0.0046 (7) −0.0011 (6) −0.0007 (7)
C9 0.0379 (10) 0.0355 (10) 0.0462 (10) −0.0049 (8) 0.0031 (8) −0.0008 (8)
C10 0.0544 (12) 0.0365 (10) 0.0526 (12) 0.0058 (9) 0.0034 (10) −0.0034 (9)
C11 0.0418 (11) 0.0531 (13) 0.0513 (12) 0.0102 (10) 0.0028 (9) −0.0072 (10)
C12 0.0310 (10) 0.0535 (13) 0.0494 (11) −0.0034 (9) 0.0057 (8) 0.0002 (9)
C13 0.0315 (9) 0.0409 (10) 0.0389 (9) −0.0042 (8) −0.0020 (7) 0.0016 (8)
C14 0.0513 (12) 0.0435 (10) 0.0391 (9) −0.0056 (10) 0.0053 (8) −0.0027 (9)
C15 0.0318 (9) 0.0306 (9) 0.0372 (9) −0.0056 (7) 0.0066 (7) −0.0007 (7)
C16 0.0406 (10) 0.0294 (8) 0.0391 (9) −0.0029 (7) 0.0018 (7) −0.0018 (7)
C17 0.0341 (9) 0.0512 (12) 0.0492 (11) −0.0046 (9) 0.0052 (8) −0.0058 (9)
C18 0.0379 (11) 0.089 (2) 0.0546 (13) −0.0233 (12) 0.0085 (9) −0.0164 (13)
C19 0.0761 (18) 0.0632 (16) 0.0534 (13) −0.0401 (15) 0.0107 (12) −0.0014 (12)
C20 0.0856 (19) 0.0415 (12) 0.0645 (15) −0.0188 (13) 0.0017 (13) 0.0086 (11)
C21 0.0495 (12) 0.0368 (10) 0.0564 (12) −0.0059 (9) −0.0017 (9) 0.0050 (9)
C22 0.0328 (9) 0.0340 (9) 0.0326 (8) −0.0063 (7) 0.0012 (7) −0.0034 (7)
C23 0.0263 (8) 0.0258 (8) 0.0396 (9) 0.0011 (6) −0.0013 (6) 0.0008 (7)
C24 0.0260 (8) 0.0266 (8) 0.0382 (8) 0.0013 (6) −0.0028 (6) 0.0002 (7)
C25 0.0309 (9) 0.0336 (9) 0.0461 (10) −0.0024 (8) 0.0034 (7) −0.0017 (8)
C26 0.0419 (10) 0.0466 (11) 0.0429 (10) −0.0020 (9) 0.0067 (8) −0.0078 (8)
C27 0.0472 (11) 0.0480 (12) 0.0473 (11) −0.0063 (10) −0.0032 (9) −0.0140 (9)
C28 0.0404 (10) 0.0452 (11) 0.0520 (11) −0.0149 (9) −0.0066 (8) −0.0033 (9)
C29 0.0307 (9) 0.0357 (9) 0.0398 (9) −0.0026 (8) −0.0029 (7) 0.0036 (8)
N1 0.0307 (7) 0.0322 (8) 0.0385 (8) −0.0061 (6) 0.0031 (6) 0.0001 (6)
N2 0.0345 (7) 0.0323 (7) 0.0376 (7) −0.0043 (6) 0.0003 (6) −0.0011 (6)
O1 0.0343 (7) 0.0413 (8) 0.0778 (11) −0.0062 (6) 0.0092 (7) 0.0116 (8)
O2 0.0440 (8) 0.0613 (10) 0.0410 (7) −0.0221 (7) 0.0020 (6) 0.0007 (7)
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Geometric parameters (Å, °)

C1—C2 1.380 (3) C15—H15 0.98
C1—C6 1.385 (3) C16—N2 1.460 (2)
C1—H1 0.93 C16—H16A 0.97
C2—C3 1.374 (3) C16—H16B 0.97
C2—H2 0.93 C17—C22 1.385 (3)
C3—C4 1.371 (3) C17—C18 1.395 (3)
C3—H3 0.93 C17—H17 0.93
C4—C5 1.391 (3) C18—C19 1.372 (4)
C4—H4 0.93 C18—H18 0.93
C5—C6 1.388 (3) C19—C20 1.369 (4)
C5—H5 0.93 C19—H19 0.93
C6—C7 1.508 (2) C20—C21 1.382 (3)
C7—N1 1.283 (2) C20—H20 0.93
C7—C8 1.469 (3) C21—C22 1.389 (3)
C8—C9 1.399 (3) C21—H21 0.93
C8—C13 1.419 (2) C22—C23 1.500 (2)
C9—C10 1.378 (3) C23—N2 1.284 (2)
C9—H9 0.93 C23—C24 1.477 (2)
C10—C11 1.388 (3) C24—C25 1.399 (2)
C10—H10 0.93 C24—C29 1.411 (2)
C11—C12 1.376 (3) C25—C26 1.383 (3)
C11—H11 0.93 C25—H25 0.93
C12—C13 1.389 (3) C26—C27 1.386 (3)
C12—H12 0.93 C26—H26 0.93
C13—O1 1.346 (3) C27—C28 1.376 (3)
C14—C15 1.525 (3) C27—H27 0.93
C14—H14A 0.96 C28—C29 1.388 (3)
C14—H14B 0.96 C28—H28 0.93
C14—H14C 0.96 C29—O2 1.347 (2)
C15—N1 1.460 (2) O1—H1A 0.82
C15—C16 1.525 (3) O2—H2A 0.82
C2—C1—C6 120.49 (18) C16—C15—H15 109.5
C2—C1—H1 119.8 N2—C16—C15 109.55 (15)
C6—C1—H1 119.8 N2—C16—H16A 109.8
C3—C2—C1 120.01 (18) C15—C16—H16A 109.8
C3—C2—H2 120 N2—C16—H16B 109.8
C1—C2—H2 120 C15—C16—H16B 109.8
C4—C3—C2 120.00 (18) H16A—C16—H16B 108.2
C4—C3—H3 120 C22—C17—C18 119.5 (2)
C2—C3—H3 120 C22—C17—H17 120.2
C3—C4—C5 120.72 (19) C18—C17—H17 120.2
C3—C4—H4 119.6 C19—C18—C17 120.0 (2)
C5—C4—H4 119.6 C19—C18—H18 120
C6—C5—C4 119.26 (18) C17—C18—H18 120
C6—C5—H5 120.4 C20—C19—C18 120.5 (2)
C4—C5—H5 120.4 C20—C19—H19 119.7
C1—C6—C5 119.48 (17) C18—C19—H19 119.7
C1—C6—C7 118.56 (16) C19—C20—C21 120.3 (2)
C5—C6—C7 121.90 (16) C19—C20—H20 119.9
N1—C7—C8 119.60 (16) C21—C20—H20 119.9
N1—C7—C6 122.34 (17) C20—C21—C22 119.8 (2)
C8—C7—C6 118.02 (15) C20—C21—H21 120.1
C9—C8—C13 117.66 (17) C22—C21—H21 120.1
C9—C8—C7 121.20 (17) C17—C22—C21 119.81 (18)
C13—C8—C7 121.13 (15) C17—C22—C23 121.07 (18)
C10—C9—C8 122.01 (19) C21—C22—C23 119.12 (16)
C10—C9—H9 119 N2—C23—C24 118.18 (15)
C8—C9—H9 119 N2—C23—C22 123.25 (16)
C9—C10—C11 119.3 (2) C24—C23—C22 118.55 (15)
C9—C10—H10 120.4 C25—C24—C29 117.87 (16)
C11—C10—H10 120.4 C25—C24—C23 121.07 (15)
C12—C11—C10 120.5 (2) C29—C24—C23 121.06 (15)
C12—C11—H11 119.8 C26—C25—C24 121.64 (18)
C10—C11—H11 119.8 C26—C25—H25 119.2
C11—C12—C13 120.7 (2) C24—C25—H25 119.2
C11—C12—H12 119.6 C25—C26—C27 119.29 (19)
C13—C12—H12 119.6 C25—C26—H26 120.4
O1—C13—C12 118.80 (18) C27—C26—H26 120.4
O1—C13—C8 121.39 (17) C28—C27—C26 120.58 (19)
C12—C13—C8 119.81 (18) C28—C27—H27 119.7
C15—C14—H14A 109.5 C26—C27—H27 119.7
C15—C14—H14B 109.5 C27—C28—C29 120.45 (19)
H14A—C14—H14B 109.5 C27—C28—H28 119.8
C15—C14—H14C 109.5 C29—C28—H28 119.8
H14A—C14—H14C 109.5 O2—C29—C28 117.95 (17)
H14B—C14—H14C 109.5 O2—C29—C24 121.87 (16)
N1—C15—C14 108.39 (15) C28—C29—C24 120.17 (17)
N1—C15—C16 109.14 (14) C7—N1—C15 122.13 (16)
C14—C15—C16 110.66 (15) C23—N2—C16 121.53 (16)
N1—C15—H15 109.5 C13—O1—H1A 109.5
C14—C15—H15 109.5 C29—O2—H2A 109.5
C6—C1—C2—C3 2.0 (3) C19—C20—C21—C22 −0.1 (4)
C1—C2—C3—C4 −0.7 (3) C18—C17—C22—C21 0.4 (3)
C2—C3—C4—C5 −0.5 (4) C18—C17—C22—C23 179.17 (18)
C3—C4—C5—C6 0.5 (4) C20—C21—C22—C17 −0.2 (3)
C2—C1—C6—C5 −1.9 (3) C20—C21—C22—C23 −179.00 (19)
C2—C1—C6—C7 175.34 (18) C17—C22—C23—N2 −93.9 (2)
C4—C5—C6—C1 0.7 (3) C21—C22—C23—N2 84.9 (2)
C4—C5—C6—C7 −176.5 (2) C17—C22—C23—C24 87.8 (2)
C1—C6—C7—N1 −87.8 (2) C21—C22—C23—C24 −93.4 (2)
C5—C6—C7—N1 89.5 (2) N2—C23—C24—C25 172.54 (17)
C1—C6—C7—C8 89.8 (2) C22—C23—C24—C25 −9.1 (2)
C5—C6—C7—C8 −92.9 (2) N2—C23—C24—C29 −7.8 (2)
N1—C7—C8—C9 −171.73 (18) C22—C23—C24—C29 170.61 (16)
C6—C7—C8—C9 10.6 (2) C29—C24—C25—C26 0.5 (3)
N1—C7—C8—C13 7.3 (3) C23—C24—C25—C26 −179.84 (18)
C6—C7—C8—C13 −170.35 (16) C24—C25—C26—C27 0.3 (3)
C13—C8—C9—C10 0.1 (3) C25—C26—C27—C28 −0.9 (3)
C7—C8—C9—C10 179.19 (17) C26—C27—C28—C29 0.7 (3)
C8—C9—C10—C11 1.1 (3) C27—C28—C29—O2 −178.9 (2)
C9—C10—C11—C12 −0.7 (3) C27—C28—C29—C24 0.2 (3)
C10—C11—C12—C13 −0.8 (3) C25—C24—C29—O2 178.35 (17)
C11—C12—C13—O1 −178.8 (2) C23—C24—C29—O2 −1.4 (3)
C11—C12—C13—C8 2.0 (3) C25—C24—C29—C28 −0.7 (3)
C9—C8—C13—O1 179.18 (19) C23—C24—C29—C28 179.59 (17)
C7—C8—C13—O1 0.1 (3) C8—C7—N1—C15 177.40 (14)
C9—C8—C13—C12 −1.7 (3) C6—C7—N1—C15 −5.0 (3)
C7—C8—C13—C12 179.27 (17) C14—C15—N1—C7 −111.3 (2)
N1—C15—C16—N2 −66.08 (18) C16—C15—N1—C7 128.14 (18)
C14—C15—C16—N2 174.74 (15) C24—C23—N2—C16 −175.93 (15)
C22—C17—C18—C19 −0.2 (3) C22—C23—N2—C16 5.8 (3)
C17—C18—C19—C20 −0.1 (4) C15—C16—N2—C23 131.47 (17)
C18—C19—C20—C21 0.3 (4)
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Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
O1—H1A···N1 0.82 1.84 2.573 (2) 147
O2—H2A···N2 0.82 1.83 2.553 (2) 147
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5392).

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 datablocks global, I. DOI: 10.1107/S1600536810015291/hb5392sup1.cif

e-66-o1256-sup1.cif (22.5KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015291/hb5392Isup2.hkl

e-66-o1256-Isup2.hkl (144.3KB, hkl)

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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