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Acta Crystallogr Sect E Struct Rep Online. 2009 March 1; 65(Pt 3): o477.
Published online 2009 February 6. doi:  10.1107/S1600536809003869
PMCID: PMC2968506

(E)-4-[(4-Methoxy­phen­yl)imino­meth­yl]-N,N-dimethyl­aniline

Abstract

The title compound, C16H18N2O, an N-benzyl­ideneaniline derivative with substituents on both aromatic rings, crystallizes with two independent mol­ecules (A and B) in the asymmetric unit. Both mol­ecules exist in the E configuration. The dihedral angle between the two aromatic rings is 8.20 (5)° for mol­ecule A and 12.52 (6)° for mol­ecule B, and the imino C—N torsion angle (τ) is 7.1 (2)° for mol­ecule A and −14.7 (2)° for mol­ecule B. In the crystal structure, mol­ecules are arranged in stacks which propagate along the a-axis direction. The crystal structure is stabilized by a number of weak C—H(...)π inter­actions.

Related literature

For the conformational analysis of similar compounds, see: Bernstein et al. (1981 [triangle]); For the structures of related compounds, see: Clegg et al. (1996 [triangle]), Ahmet et al. (1994 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o477-scheme1.jpg

Experimental

Crystal data

  • C16H18N2O
  • M r = 254.32
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o477-efi1.jpg
  • a = 9.6638 (6) Å
  • b = 28.5819 (15) Å
  • c = 9.9729 (7) Å
  • β = 98.741 (5)°
  • V = 2722.6 (3) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 173 (2) K
  • 0.33 × 0.30 × 0.28 mm

Data collection

  • Stoe IPDS-2 diffractometer
  • Absorption correction: none
  • 23112 measured reflections
  • 5128 independent reflections
  • 3960 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.093
  • S = 1.04
  • 5128 reflections
  • 350 parameters
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.15 e Å−3

Data collection: X-AREA (Stoe & Cie, 2006 [triangle]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2006 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Intermolecular C—H(...)π interactions (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809003869/nc2130sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003869/nc2130Isup2.hkl

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

Acknowledgments

LS and KR gratefully acknowledge financial support from the University Grants Commission, India [File No.3237/2006(SR)].

supplementary crystallographic information

Comment

Interest in the optical properties of N-benzylideneaniline derivatives is focused on potential applications, such as liquid crystalline and non-linear optical properties. The second harmonic generation properties have been widely studied (Clegg et al., 1996 and references therein). Bernstein et al. (1981) have shown by ab initio calculations on benzylideneaniline and related molecules, that rotations about the Ph—N bond of up to 45° from a planar conformation are stabilizing, while rotations about the Ph—C bond are destabilizing, and the most stable free-molecule conformation is non-planar. In contrast, benzylideneaniline derivatives with substituents on one or both aromatic rings display a range of conformations in the solid state (Clegg et al., 1996).

The asymmetric unit of the title compound contains two crystallographically independent molecules (A and B), as shown in Fig. 1. Both molecules exist in the E-configuration and their bond lengths and angles are comparable to those in related structures (Ahmet et al., 1994; Clegg et al., 1996). The dihedral angle between the two aromatic rings is 8.20 (5)° for molecule A and 12.52 (6)° for molecule B, and the imino C—N torsion angle (τ) is 7.05 (18)° in molecule A and -14.68 (18)° in molecule B (see Table 1). This slight difference in the conformation of the two molecules is illustrated by the Auto-Fit diagram (r.m.s. Bond Fit = 0.0028 Å; r.m.s Angle Fit = 0.566°; Spek, 2008), as shown in Fig. 2.

In the crystal structure molecules A and B (i.e. the mean planes through all the non-H atoms in each molecule) are inclinded to one another by 68.8 (5)°. The molecules pack in stacks along the a direction (Fig. 3), and the crystal structure is stabilized by a number of C—H···π interactions (Table 2).

Experimental

The title compound (CAS Registry No. 97221–11-9) was prepared by the reaction of 4-dimethylaminobenzaldehyde (2 mmol) with 4-methoxyaniline (2 mmol) in absolute ethanol (10 ml) for one day at room temperature. The solvent was evaporated and the product was recrystallized from acteone, giving yellow block-like crystals suitable for X-ray analysis.

Refinement

H atoms were included in calculated positions and treated as riding atoms: C—H = 0.95 - 0.98 Å, with Uiso = 1.2 or 1.5Ueq(parent C-atom).

Figures

Fig. 1.
View of the two independent molecules (A & B) of the title compound, showing the atom-labeling scheme and displacement ellipsoids drawn at the 50% probability level (H atoms are represented by circles of arbitrary radii).
Fig. 2.
The Auto-Fit (Spek, 2003) diagram of molecules A (in black) and B (in red).
Fig. 3.
A view along the a axis of the crystal packing of the title compound [molecule A is in black, molecule B is in red].

Crystal data

C16H18N2OF(000) = 1088
Mr = 254.32Dx = 1.241 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 18324 reflections
a = 9.6638 (6) Åθ = 1.4–26.1°
b = 28.5819 (15) ŵ = 0.08 mm1
c = 9.9729 (7) ÅT = 173 K
β = 98.741 (5)°Block, yellow
V = 2722.6 (3) Å30.33 × 0.30 × 0.28 mm
Z = 8

Data collection

Stoe IPDS-2 diffractometer3960 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.036
graphiteθmax = 25.7°, θmin = 1.4°
Detector resolution: 6.67 pixels mm-1h = −11→10
[var phi] and ω scansk = −34→34
23112 measured reflectionsl = −12→12
5128 independent 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)] = 0.035H-atom parameters constrained
wR(F2) = 0.093w = 1/[σ2(Fo2) + (0.057P)2 + 0.0294P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
5128 reflectionsΔρmax = 0.16 e Å3
350 parametersΔρmin = −0.15 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0072 (11)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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
O1−0.01231 (8)0.26535 (3)0.41055 (9)0.0343 (3)
N10.18794 (10)0.09281 (3)0.61633 (10)0.0310 (3)
N20.34868 (12)−0.10828 (4)0.89245 (11)0.0409 (3)
C10.02582 (12)0.22093 (4)0.45339 (11)0.0277 (3)
C20.16891 (12)0.21336 (4)0.48916 (11)0.0302 (3)
C30.21674 (12)0.17052 (4)0.54052 (11)0.0289 (3)
C40.12485 (12)0.13401 (4)0.55728 (11)0.0273 (3)
C5−0.01789 (12)0.14196 (4)0.51769 (12)0.0326 (4)
C6−0.06724 (12)0.18490 (4)0.46633 (12)0.0315 (3)
C70.11725 (12)0.05582 (4)0.62753 (11)0.0298 (4)
C80.17909 (12)0.01367 (4)0.69266 (11)0.0283 (3)
C90.32174 (12)0.01043 (4)0.74581 (12)0.0317 (4)
C100.37765 (12)−0.02905 (4)0.81114 (12)0.0333 (4)
C110.29289 (13)−0.06815 (4)0.82823 (11)0.0307 (3)
C120.15020 (13)−0.06498 (4)0.77430 (12)0.0342 (3)
C130.09608 (12)−0.02504 (4)0.70861 (12)0.0327 (4)
C14−0.15718 (13)0.27386 (5)0.36613 (15)0.0415 (4)
C150.25698 (16)−0.14624 (5)0.91713 (15)0.0501 (5)
C160.48167 (14)−0.10627 (6)0.98195 (16)0.0541 (5)
O20.48614 (9)0.26329 (3)0.41654 (8)0.0363 (3)
N30.66974 (10)0.09634 (4)0.67327 (10)0.0330 (3)
N40.84937 (12)−0.10741 (3)0.91646 (10)0.0355 (3)
C210.53069 (11)0.22039 (4)0.46791 (11)0.0288 (3)
C220.56508 (12)0.21854 (4)0.60834 (11)0.0299 (3)
C230.61013 (12)0.17706 (4)0.67068 (11)0.0300 (3)
C240.62180 (11)0.13625 (4)0.59646 (11)0.0284 (3)
C250.58756 (12)0.13886 (4)0.45565 (12)0.0324 (4)
C260.54305 (12)0.18050 (4)0.39161 (11)0.0314 (4)
C270.65947 (12)0.05552 (4)0.62163 (12)0.0310 (4)
C280.70670 (12)0.01390 (4)0.69932 (12)0.0293 (3)
C290.76315 (12)0.01597 (4)0.83718 (12)0.0317 (3)
C300.80752 (13)−0.02356 (4)0.90926 (12)0.0321 (3)
C310.79938 (12)−0.06800 (4)0.84664 (11)0.0288 (3)
C320.73941 (12)−0.07010 (4)0.70913 (11)0.0300 (3)
C330.69511 (12)−0.03003 (4)0.63833 (12)0.0308 (4)
C340.45066 (15)0.26764 (5)0.27361 (13)0.0444 (5)
C350.89078 (16)−0.10601 (5)1.06188 (13)0.0449 (4)
C360.83689 (16)−0.15253 (4)0.85068 (14)0.0433 (4)
H20.233500.237600.478200.0360*
H30.314600.165700.565100.0350*
H5−0.082500.117500.526100.0390*
H6−0.164900.189600.440000.0380*
H70.020300.055800.591900.0360*
H90.381300.036300.736300.0380*
H100.47490−0.030100.845400.0400*
H120.09010−0.090700.783200.0410*
H13−0.00080−0.024000.673200.0390*
H14A−0.192100.252000.293200.0620*
H14B−0.209200.269500.442200.0620*
H14C−0.169900.306000.332400.0620*
H15A0.19700−0.136200.982600.0750*
H15B0.19860−0.155100.831800.0750*
H15C0.31320−0.173200.953700.0750*
H16A0.47180−0.087001.061300.0810*
H16B0.55260−0.092400.933500.0810*
H16C0.51050−0.138001.011500.0810*
H220.557500.245800.661200.0360*
H230.633800.176200.766700.0360*
H250.594800.111600.402600.0390*
H260.521100.181700.295500.0380*
H270.619500.052100.529100.0370*
H290.770900.045400.881800.0380*
H300.84430−0.021001.002900.0380*
H320.72930−0.099500.664400.0360*
H330.65560−0.032500.545400.0370*
H34A0.532100.259600.230400.0670*
H34B0.373200.246400.241100.0670*
H34C0.422200.299900.250600.0670*
H35A0.96730−0.083501.084500.0670*
H35B0.81080−0.096401.105200.0670*
H35C0.92240−0.137101.094600.0670*
H36A0.88130−0.151400.768700.0650*
H36B0.73770−0.160500.826000.0650*
H36C0.88320−0.176300.912700.0650*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0305 (4)0.0322 (5)0.0398 (5)−0.0008 (4)0.0042 (4)0.0072 (4)
N10.0302 (5)0.0301 (5)0.0332 (5)0.0002 (4)0.0069 (4)0.0009 (4)
N20.0426 (6)0.0360 (6)0.0439 (6)0.0030 (5)0.0063 (5)0.0081 (5)
C10.0319 (6)0.0292 (6)0.0224 (5)−0.0001 (5)0.0059 (4)−0.0005 (4)
C20.0278 (6)0.0318 (6)0.0320 (6)−0.0057 (5)0.0080 (5)−0.0021 (5)
C30.0241 (5)0.0330 (6)0.0299 (6)−0.0016 (5)0.0053 (4)−0.0030 (5)
C40.0282 (6)0.0290 (6)0.0252 (5)−0.0020 (5)0.0059 (4)−0.0027 (4)
C50.0277 (6)0.0306 (6)0.0397 (7)−0.0051 (5)0.0060 (5)0.0004 (5)
C60.0238 (5)0.0356 (7)0.0347 (6)−0.0023 (5)0.0031 (5)−0.0002 (5)
C70.0286 (6)0.0340 (7)0.0265 (6)−0.0007 (5)0.0037 (5)−0.0024 (5)
C80.0306 (6)0.0306 (6)0.0243 (5)−0.0012 (5)0.0066 (4)−0.0027 (5)
C90.0298 (6)0.0339 (7)0.0326 (6)−0.0040 (5)0.0084 (5)−0.0003 (5)
C100.0265 (6)0.0380 (7)0.0357 (6)0.0010 (5)0.0056 (5)0.0008 (5)
C110.0356 (6)0.0311 (6)0.0267 (6)0.0035 (5)0.0087 (5)−0.0017 (5)
C120.0355 (6)0.0308 (6)0.0363 (6)−0.0058 (5)0.0059 (5)−0.0004 (5)
C130.0281 (6)0.0357 (7)0.0335 (6)−0.0028 (5)0.0024 (5)−0.0021 (5)
C140.0347 (7)0.0388 (7)0.0492 (8)0.0041 (6)0.0005 (6)0.0079 (6)
C150.0593 (9)0.0327 (7)0.0560 (9)−0.0012 (7)0.0018 (7)0.0090 (6)
C160.0371 (7)0.0544 (9)0.0694 (10)0.0074 (7)0.0036 (7)0.0241 (8)
O20.0405 (5)0.0331 (5)0.0344 (5)−0.0009 (4)0.0030 (4)0.0086 (4)
N30.0348 (6)0.0309 (6)0.0339 (5)0.0029 (4)0.0076 (4)0.0024 (4)
N40.0478 (6)0.0270 (5)0.0318 (5)0.0025 (5)0.0069 (5)−0.0020 (4)
C210.0220 (5)0.0314 (6)0.0331 (6)−0.0040 (5)0.0048 (5)0.0059 (5)
C220.0331 (6)0.0266 (6)0.0305 (6)−0.0045 (5)0.0069 (5)−0.0006 (5)
C230.0312 (6)0.0324 (6)0.0263 (6)−0.0046 (5)0.0042 (5)0.0015 (5)
C240.0245 (6)0.0299 (6)0.0316 (6)−0.0012 (5)0.0067 (4)0.0014 (5)
C250.0316 (6)0.0352 (7)0.0311 (6)0.0000 (5)0.0071 (5)−0.0037 (5)
C260.0283 (6)0.0397 (7)0.0261 (6)−0.0025 (5)0.0036 (5)0.0006 (5)
C270.0274 (6)0.0335 (7)0.0323 (6)−0.0013 (5)0.0054 (5)0.0005 (5)
C280.0258 (6)0.0304 (6)0.0327 (6)−0.0015 (5)0.0081 (5)−0.0006 (5)
C290.0344 (6)0.0277 (6)0.0340 (6)−0.0014 (5)0.0082 (5)−0.0058 (5)
C300.0374 (6)0.0317 (6)0.0273 (6)−0.0005 (5)0.0057 (5)−0.0038 (5)
C310.0288 (6)0.0280 (6)0.0313 (6)−0.0016 (5)0.0101 (5)−0.0016 (5)
C320.0299 (6)0.0288 (6)0.0324 (6)−0.0027 (5)0.0085 (5)−0.0057 (5)
C330.0286 (6)0.0356 (7)0.0286 (6)−0.0031 (5)0.0055 (5)−0.0035 (5)
C340.0446 (8)0.0504 (9)0.0359 (7)0.0018 (6)−0.0017 (6)0.0130 (6)
C350.0607 (9)0.0353 (7)0.0365 (7)0.0045 (7)0.0008 (6)0.0018 (6)
C360.0577 (9)0.0266 (7)0.0446 (7)0.0030 (6)0.0048 (6)−0.0026 (6)

Geometric parameters (Å, °)

O1—C11.3720 (14)C14—H14C0.9800
O1—C141.4237 (15)C15—H15A0.9800
O2—C341.4200 (15)C15—H15B0.9800
O2—C211.3727 (14)C15—H15C0.9800
N1—C71.2728 (15)C16—H16A0.9800
N1—C41.4128 (15)C16—H16B0.9800
N2—C161.4502 (19)C16—H16C0.9800
N2—C111.3826 (16)C21—C221.3904 (15)
N2—C151.4455 (19)C21—C261.3859 (16)
N3—C241.4124 (16)C22—C231.3782 (16)
N3—C271.2731 (16)C23—C241.3952 (16)
N4—C311.3729 (15)C24—C251.3949 (16)
N4—C351.4452 (16)C25—C261.3878 (16)
N4—C361.4436 (15)C27—C281.4547 (16)
C1—C61.3861 (16)C28—C291.4012 (17)
C1—C21.3915 (17)C28—C331.3922 (16)
C2—C31.3796 (16)C29—C301.3724 (16)
C3—C41.3966 (16)C30—C311.4123 (16)
C4—C51.3946 (17)C31—C321.4066 (15)
C5—C61.3863 (16)C32—C331.3790 (16)
C7—C81.4534 (16)C22—H220.9500
C8—C131.3899 (16)C23—H230.9500
C8—C91.4028 (17)C25—H250.9500
C9—C101.3721 (16)C26—H260.9500
C10—C111.4112 (17)C27—H270.9500
C11—C121.4048 (18)C29—H290.9500
C12—C131.3790 (16)C30—H300.9500
C2—H20.9500C32—H320.9500
C3—H30.9500C33—H330.9500
C5—H50.9500C34—H34A0.9800
C6—H60.9500C34—H34B0.9800
C7—H70.9500C34—H34C0.9800
C9—H90.9500C35—H35A0.9800
C10—H100.9500C35—H35B0.9800
C12—H120.9500C35—H35C0.9800
C13—H130.9500C36—H36A0.9800
C14—H14B0.9800C36—H36B0.9800
C14—H14A0.9800C36—H36C0.9800
C1—O1—C14117.38 (9)H16B—C16—H16C110.00
C21—O2—C34117.84 (9)N2—C16—H16A109.00
C4—N1—C7121.70 (10)N2—C16—H16B109.00
C11—N2—C16119.93 (12)N2—C16—H16C109.00
C15—N2—C16115.71 (12)H16A—C16—H16B109.00
C11—N2—C15119.71 (11)O2—C21—C22115.04 (10)
C24—N3—C27121.45 (10)O2—C21—C26125.33 (10)
C35—N4—C36118.17 (10)C22—C21—C26119.63 (10)
C31—N4—C35120.58 (10)C21—C22—C23119.86 (10)
C31—N4—C36120.25 (10)C22—C23—C24121.69 (10)
C2—C1—C6119.61 (11)N3—C24—C23115.71 (10)
O1—C1—C6124.69 (10)N3—C24—C25126.68 (10)
O1—C1—C2115.67 (10)C23—C24—C25117.61 (10)
C1—C2—C3119.80 (11)C24—C25—C26121.24 (11)
C2—C3—C4121.62 (11)C21—C26—C25119.96 (10)
N1—C4—C3115.51 (10)N3—C27—C28122.35 (11)
N1—C4—C5126.83 (10)C27—C28—C29122.14 (10)
C3—C4—C5117.64 (10)C27—C28—C33120.46 (11)
C4—C5—C6121.25 (11)C29—C28—C33117.40 (11)
C1—C6—C5120.03 (11)C28—C29—C30121.55 (11)
N1—C7—C8122.55 (11)C29—C30—C31121.12 (11)
C7—C8—C9122.50 (10)N4—C31—C30121.47 (10)
C7—C8—C13120.38 (11)N4—C31—C32121.37 (10)
C9—C8—C13117.09 (10)C30—C31—C32117.16 (10)
C8—C9—C10121.81 (11)C31—C32—C33120.91 (11)
C9—C10—C11120.98 (11)C28—C33—C32121.82 (11)
N2—C11—C12121.46 (11)C21—C22—H22120.00
C10—C11—C12117.17 (10)C23—C22—H22120.00
N2—C11—C10121.35 (11)C22—C23—H23119.00
C11—C12—C13120.97 (11)C24—C23—H23119.00
C8—C13—C12121.97 (11)C24—C25—H25119.00
C1—C2—H2120.00C26—C25—H25119.00
C3—C2—H2120.00C21—C26—H26120.00
C4—C3—H3119.00C25—C26—H26120.00
C2—C3—H3119.00N3—C27—H27119.00
C4—C5—H5119.00C28—C27—H27119.00
C6—C5—H5119.00C28—C29—H29119.00
C5—C6—H6120.00C30—C29—H29119.00
C1—C6—H6120.00C29—C30—H30119.00
C8—C7—H7119.00C31—C30—H30119.00
N1—C7—H7119.00C31—C32—H32120.00
C8—C9—H9119.00C33—C32—H32120.00
C10—C9—H9119.00C28—C33—H33119.00
C11—C10—H10119.00C32—C33—H33119.00
C9—C10—H10120.00O2—C34—H34A109.00
C13—C12—H12119.00O2—C34—H34B109.00
C11—C12—H12120.00O2—C34—H34C110.00
C8—C13—H13119.00H34A—C34—H34B109.00
C12—C13—H13119.00H34A—C34—H34C109.00
O1—C14—H14B109.00H34B—C34—H34C109.00
O1—C14—H14C109.00N4—C35—H35A109.00
O1—C14—H14A109.00N4—C35—H35B109.00
H14A—C14—H14B110.00N4—C35—H35C110.00
H14A—C14—H14C109.00H35A—C35—H35B109.00
H14B—C14—H14C109.00H35A—C35—H35C109.00
N2—C15—H15C109.00H35B—C35—H35C110.00
H15A—C15—H15B109.00N4—C36—H36A109.00
H15A—C15—H15C109.00N4—C36—H36B109.00
N2—C15—H15A109.00N4—C36—H36C110.00
N2—C15—H15B109.00H36A—C36—H36B110.00
H15B—C15—H15C109.00H36A—C36—H36C109.00
H16A—C16—H16C110.00H36B—C36—H36C109.00
C14—O1—C1—C2176.72 (10)C13—C8—C9—C10−0.17 (17)
C14—O1—C1—C6−5.23 (16)C9—C8—C13—C120.37 (17)
C34—O2—C21—C26−0.55 (17)C7—C8—C13—C12−177.57 (11)
C34—O2—C21—C22179.41 (11)C8—C9—C10—C11−0.38 (18)
C4—N1—C7—C8−177.55 (10)C9—C10—C11—C120.72 (17)
C7—N1—C4—C57.05 (18)C9—C10—C11—N2179.19 (11)
C7—N1—C4—C3−174.49 (11)N2—C11—C12—C13−179.00 (11)
C15—N2—C11—C10175.35 (11)C10—C11—C12—C13−0.52 (17)
C16—N2—C11—C12−161.06 (12)C11—C12—C13—C8−0.02 (18)
C15—N2—C11—C12−6.25 (17)O2—C21—C22—C23179.55 (10)
C16—N2—C11—C1020.54 (17)C26—C21—C22—C23−0.48 (17)
C27—N3—C24—C25−14.68 (18)O2—C21—C26—C25−179.09 (11)
C27—N3—C24—C23166.32 (11)C22—C21—C26—C250.95 (17)
C24—N3—C27—C28−179.28 (10)C21—C22—C23—C24−0.35 (18)
C35—N4—C31—C3010.32 (18)C22—C23—C24—N3179.77 (11)
C35—N4—C31—C32−170.47 (12)C22—C23—C24—C250.68 (17)
C36—N4—C31—C32−2.15 (18)N3—C24—C25—C26−179.18 (11)
C36—N4—C31—C30178.65 (12)C23—C24—C25—C26−0.20 (17)
O1—C1—C6—C5−176.45 (11)C24—C25—C26—C21−0.61 (18)
C2—C1—C6—C51.53 (17)N3—C27—C28—C291.76 (18)
C6—C1—C2—C3−1.72 (17)N3—C27—C28—C33−179.18 (11)
O1—C1—C2—C3176.44 (10)C27—C28—C29—C30−179.90 (11)
C1—C2—C3—C40.32 (17)C33—C28—C29—C301.01 (18)
C2—C3—C4—C51.23 (16)C27—C28—C33—C32179.75 (11)
C2—C3—C4—N1−177.38 (10)C29—C28—C33—C32−1.15 (18)
C3—C4—C5—C6−1.41 (17)C28—C29—C30—C310.70 (19)
N1—C4—C5—C6177.02 (11)C29—C30—C31—N4177.00 (12)
C4—C5—C6—C10.06 (18)C29—C30—C31—C32−2.24 (18)
N1—C7—C8—C9−1.15 (18)N4—C31—C32—C33−177.13 (11)
N1—C7—C8—C13176.68 (11)C30—C31—C32—C332.11 (17)
C7—C8—C9—C10177.73 (11)C31—C32—C33—C28−0.44 (18)

Table 2 Intermolecular C—H···π interactions (Å, °)

D - H···CgD—HH···CgD—H···Cg
C3—H3···Cg30.952.63152
C6—H6···Cg3i0.952.81142
C10—H10···Cg40.952.88145
C13—H13···Cg4i0.952.73137
C30—H30···Cg2ii0.952.94136
C34—H34A···Cg1iii0.952.96114
C36—H36A···Cg1iv0.952.91156

Centroids: Cg1 = ring C1–C6; Cg2 = ring C8–C13; Cg3 = ring C21–C26; Cg4 = ring C28–C33. Symmetry codes: (i) -1+x, y, z; (ii) 1-x,-y,2-z; (iii) 1/2+x,1/2-y,-1/2+z; (iv) 1-x,-y,1-z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2130).

References

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