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Acta Crystallogr Sect E Struct Rep Online. 2009 March 1; 65(Pt 3): o593.
Published online 2009 February 25. doi:  10.1107/S1600536809006291
PMCID: PMC2968562

(2,6-Diisopropyl­phen­yl)(2-thienylmethyl­ene)amine

Abstract

The title compound, C17H21NS, was prepared by the condensation of thio­phene-2-carbaldehyde with 2,6-diiso­propyl­aniline. It crystallizes with two mol­ecules in the asymmetric unit. The mol­ecules are inter­connected via a C—H(...)N hydrogen bond. The dihedral angles between the thio­phene and phenyl rings are 81.7 (7) and 85.5 (7)°.

Related literature

For the synthetic procedure, see: Drisko & McKennis (1952 [triangle]); Wang et al. (2007 [triangle]). For related structures, see: Kazak et al. (2000 [triangle]); Małeki et al. (2007 [triangle]). For the organometallic chemistry of related ligands, see: Imhof (1997a [triangle],b [triangle]).

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Object name is e-65-0o593-scheme1.jpg

Experimental

Crystal data

  • C17H21NS
  • M r = 271.42
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o593-efi1.jpg
  • a = 10.0877 (9) Å
  • b = 14.275 (3) Å
  • c = 11.4503 (9) Å
  • β = 109.651 (8)°
  • V = 1552.8 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.20 mm−1
  • T = 173 K
  • 0.51 × 0.43 × 0.33 mm

Data collection

  • Enraf–Nonius CAD-4 diffractometer
  • Absorption correction: ψ scan (North et al., 1968 [triangle]) T min = 0.884, T max = 0.939
  • 2222 measured reflections
  • 2096 independent reflections
  • 2055 reflections with I > 2σ(I)
  • R int = 0.023
  • θmax = 23.0°
  • 3 standard reflections frequency: 120 min intensity decay: 0.02%

Refinement

  • R[F 2 > 2σ(F 2)] = 0.028
  • wR(F 2) = 0.079
  • S = 1.08
  • 2096 reflections
  • 353 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 [triangle]); cell refinement: SET4 (de Boer et al., 1984 [triangle]); data reduction: MolEN (Enraf–Nonius, 1990 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: XP (Siemens, 1990 [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/S1600536809006291/bt2882sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006291/bt2882Isup2.hkl

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

Acknowledgments

The author thanks the Deutsche Forschungsgemeinschaft (SFB 436) for financial support.

supplementary crystallographic information

Comment

In the course of a study on stoichiometric and catalytic C—H activation reactions of imines derived from 2- or 3-thiophene-carbaldehydes and aniline derivatives (Imhof, 1997a, 1997b) we synthesized the title compound that exhibits two bulky ortho-substituents at the phenyl ring. The compound crystallizes with two molecules per asymmetric unit. These molecules are interconnected by hydrogen bonds between the imine nitrogen atom as the acceptor and one of the thiophene C—H functions as the hydrogen bond donor (Table 1). Bond lengths and angles correspond to values that have been reported for related imines from 2-thiophenecarbaldehyde and aniline derivatives (Kazak et al., 2000; Małeki et al., 2007). The dihedral angles between the thiophene and the phenyl rings measure to 98.3 (7)° and 94.5 (7)°, respectively. These values are significantly higher than those observed for compounds without bulky ortho-substituents (Kazak et al., 2000: 20.8 (1)°; Małeki et al., 2007: 49.38 (6)°).

Experimental

The title compound was prepared in analogy to a literature method (Drisko & McKennis, 1952). The synthesis of the compound has also been recently described as an intermediate in the synthesis of the corresponding amine (Wang et al., 2007). The 1H-NMR spectrum of the title compound is identical to the one described in the latter publication. Single crystals are produced from a solution of the compound in light petroleum (b.p. 40–60°) and dichloromethane (20:1) at -20°. MS (EI) [m/z, %]: 271 (M+, 76), 256 (M+ - Me, 59), 214 (C13H12NS+, 100), 199 (C12H9NS+, 17), 172 (C10H6NS+, 25), 146 (C9H6S+, 33), 132 (C8H4S+, 25), 115 (C9H7+, 15), 97 (C5H5S+, 36), 91 (C7H7+, 19), 77 (C6H5+, 13), 53 (C4H5+, 8), 41 (C3H5+, 14); IR (nujol mull) [cm-1]: 1629 (CH=N); 13C-NMR (CDCl3, 298 K) [p.p.m.]: 23.5 (CH3), 28.0 (CH), 123.0 (CarH), 124.3 (CarH), 127.7 (CarH), 130.2 (CarH), 131.6 (CarH), 137.9 (Car), 142.6 (Car), 148.6 (Car), 154.9 (N=CH).

Refinement

Hydrogen atoms were positioned geometrically at distances of 0.93 Å for aromatic C—H functions and the imine C—H group, 0.98 Å for aliphatic C—H bonds and 0.96 Å for methyl groups and were refined riding on their parent atoms with isotropic displacement parameters of 1.2 times the corresponding values of their parent atoms. In the absence of significant anomalous dispersion effects, Friedel pairs were averaged.

Figures

Fig. 1.
The molecular structure of the title compound, presenting the labelling scheme and 30% probability displacement ellipsoids for non-H atoms.

Crystal data

C17H21NSF(000) = 584
Mr = 271.42Dx = 1.161 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 25 reflections
a = 10.0877 (9) Åθ = 36.5–42.8°
b = 14.275 (3) ŵ = 0.20 mm1
c = 11.4503 (9) ÅT = 173 K
β = 109.651 (8)°Cube, yellow
V = 1552.8 (4) Å30.51 × 0.43 × 0.33 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer2055 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
graphiteθmax = 23.0°, θmin = 1.9°
ω/2θ scansh = −11→10
Absorption correction: ψ scan (North et al., 1968)k = 0→15
Tmin = 0.884, Tmax = 0.939l = 0→12
2222 measured reflections3 standard reflections every 120 min
2096 independent reflections intensity decay: 0.02%

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028H-atom parameters constrained
wR(F2) = 0.079w = 1/[σ2(Fo2) + (0.0606P)2 + 0.2045P] where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
2096 reflectionsΔρmax = 0.20 e Å3
353 parametersΔρmin = −0.19 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0222 (27)

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 on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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
S10.92670 (8)0.27773 (6)0.17143 (7)0.0403 (2)
C10.8043 (4)0.3644 (2)0.1137 (3)0.0455 (8)
H10.81910.41690.07160.055*
C20.6842 (4)0.3472 (2)0.1367 (3)0.0441 (8)
H20.60650.38680.11220.053*
C30.6886 (3)0.2627 (2)0.2017 (3)0.0373 (7)
H30.61430.24070.22500.045*
C40.8135 (3)0.2166 (2)0.2268 (2)0.0304 (7)
C50.8510 (3)0.1257 (2)0.2850 (2)0.0290 (6)
H50.78870.09590.31700.035*
N10.9657 (2)0.08570 (16)0.2936 (2)0.0307 (6)
C60.9982 (3)−0.0052 (2)0.3474 (3)0.0303 (6)
C71.0936 (3)−0.0118 (2)0.4707 (3)0.0332 (7)
C81.1362 (3)−0.1004 (2)0.5183 (3)0.0402 (7)
H81.1975−0.10610.59940.048*
C91.0900 (4)−0.1802 (2)0.4487 (3)0.0459 (8)
H91.1204−0.23890.48220.055*
C100.9987 (4)−0.1719 (2)0.3292 (3)0.0481 (9)
H100.9695−0.22590.28200.058*
C110.9485 (3)−0.0855 (2)0.2764 (3)0.0371 (7)
C121.1462 (3)0.0744 (2)0.5499 (3)0.0425 (8)
H121.11230.12990.49800.051*
C131.3055 (5)0.0779 (4)0.6001 (6)0.0936 (16)
H13A1.34150.07490.53260.112*
H13B1.34050.02580.65470.112*
H13C1.33530.13540.64490.112*
C141.0880 (6)0.0770 (3)0.6541 (5)0.0860 (15)
H14A1.12850.12880.70790.103*
H14B1.11050.01960.70020.103*
H14C0.98760.08440.62110.103*
C150.8490 (4)−0.0815 (2)0.1424 (3)0.0483 (9)
H150.8103−0.01800.12610.058*
C160.7261 (4)−0.1501 (3)0.1206 (4)0.0586 (10)
H16A0.6602−0.14160.03840.070*
H16B0.6800−0.13860.18020.070*
H16C0.7611−0.21320.12960.070*
C170.9284 (4)−0.1013 (3)0.0537 (3)0.0595 (10)
H17A0.8637−0.1017−0.02990.071*
H17B0.9739−0.16110.07280.071*
H17C0.9979−0.05340.06210.071*
S21.45567 (7)0.01922 (5)0.12971 (7)0.0362 (2)
C181.3736 (3)0.1201 (2)0.0597 (3)0.0364 (7)
H181.40440.15630.00640.044*
C191.2598 (3)0.1407 (2)0.0909 (3)0.0376 (7)
H191.20270.19270.06130.045*
C201.2366 (3)0.0744 (2)0.1739 (3)0.0338 (7)
H201.16290.07850.20520.041*
C211.3337 (3)0.0036 (2)0.2034 (2)0.0299 (6)
C221.3372 (3)−0.0769 (2)0.2809 (3)0.0306 (7)
H221.2697−0.08160.31940.037*
N21.4285 (3)−0.14133 (17)0.2987 (2)0.0330 (6)
C231.4182 (3)−0.2197 (2)0.3739 (2)0.0284 (6)
C241.3357 (3)−0.2969 (2)0.3184 (3)0.0298 (6)
C251.3289 (3)−0.3717 (2)0.3932 (3)0.0336 (7)
H251.2725−0.42290.35820.040*
C261.4047 (3)−0.3717 (2)0.5197 (3)0.0346 (7)
H261.3980−0.42220.56880.041*
C271.4899 (3)−0.2964 (2)0.5719 (3)0.0351 (7)
H271.5428−0.29770.65590.042*
C281.4983 (3)−0.2185 (2)0.5012 (3)0.0318 (6)
C291.2653 (3)−0.3020 (2)0.1779 (3)0.0349 (7)
H291.2322−0.23890.14870.042*
C301.3730 (4)−0.3295 (3)0.1190 (3)0.0516 (9)
H30A1.4096−0.39050.14780.062*
H30B1.4484−0.28470.14130.062*
H30C1.3294−0.33060.03040.062*
C311.1389 (3)−0.3669 (3)0.1358 (3)0.0480 (8)
H31A1.0931−0.36080.04790.058*
H31B1.0741−0.35060.17770.058*
H31C1.1694−0.43050.15530.058*
C321.5953 (3)−0.1370 (2)0.5574 (3)0.0417 (8)
H321.5458−0.07940.52070.050*
C331.6322 (5)−0.1290 (3)0.6970 (3)0.0681 (12)
H33A1.6913−0.07530.72650.082*
H33B1.6812−0.18440.73600.082*
H33C1.5475−0.12220.71680.082*
C341.7288 (4)−0.1426 (3)0.5227 (4)0.0704 (12)
H34A1.7039−0.14160.43400.084*
H34B1.7781−0.19970.55460.084*
H34C1.7884−0.09010.55760.084*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0442 (4)0.0359 (4)0.0387 (4)0.0012 (4)0.0110 (3)0.0054 (4)
C10.065 (2)0.0341 (18)0.0314 (17)0.0049 (17)0.0084 (16)0.0048 (15)
C20.0512 (19)0.0363 (18)0.0319 (17)0.0130 (15)−0.0027 (15)0.0002 (15)
C30.0383 (15)0.0336 (18)0.0328 (16)0.0051 (14)0.0023 (13)−0.0005 (14)
C40.0334 (14)0.0325 (16)0.0187 (14)0.0017 (12)0.0000 (12)−0.0056 (13)
C50.0338 (14)0.0297 (15)0.0189 (14)−0.0001 (13)0.0028 (11)−0.0028 (13)
N10.0334 (13)0.0268 (13)0.0280 (13)0.0034 (11)0.0051 (10)0.0002 (11)
C60.0343 (14)0.0281 (16)0.0286 (16)0.0019 (12)0.0109 (12)0.0022 (13)
C70.0403 (16)0.0293 (16)0.0282 (16)0.0003 (13)0.0090 (13)0.0033 (13)
C80.0479 (17)0.0363 (17)0.0280 (16)0.0050 (15)0.0018 (14)0.0030 (15)
C90.064 (2)0.0281 (17)0.0399 (19)0.0096 (16)0.0093 (16)0.0048 (15)
C100.064 (2)0.0284 (17)0.044 (2)0.0051 (16)0.0069 (17)−0.0067 (15)
C110.0416 (16)0.0295 (16)0.0340 (17)0.0049 (13)0.0045 (14)−0.0049 (14)
C120.0499 (18)0.0313 (17)0.0337 (16)−0.0038 (15)−0.0023 (14)0.0059 (15)
C130.065 (3)0.080 (4)0.124 (4)−0.029 (3)0.016 (3)−0.031 (3)
C140.140 (4)0.055 (3)0.081 (3)−0.010 (3)0.062 (3)−0.028 (3)
C150.058 (2)0.0320 (17)0.0383 (19)0.0107 (16)−0.0054 (16)−0.0065 (15)
C160.0452 (19)0.062 (2)0.056 (2)0.0053 (17)0.0012 (18)−0.016 (2)
C170.069 (2)0.064 (2)0.0341 (18)−0.008 (2)0.0018 (16)0.0017 (19)
S20.0377 (4)0.0345 (4)0.0361 (4)0.0016 (3)0.0120 (3)0.0049 (3)
C180.0454 (17)0.0320 (16)0.0280 (15)−0.0045 (14)0.0073 (13)0.0094 (14)
C190.0380 (16)0.0284 (16)0.0393 (17)0.0013 (14)0.0034 (14)0.0053 (15)
C200.0354 (15)0.0311 (16)0.0320 (15)0.0005 (13)0.0074 (12)0.0013 (13)
C210.0335 (14)0.0277 (15)0.0216 (14)−0.0030 (12)0.0003 (11)0.0013 (13)
C220.0325 (15)0.0292 (15)0.0257 (15)−0.0037 (13)0.0038 (12)0.0001 (13)
N20.0393 (13)0.0289 (13)0.0270 (13)0.0025 (11)0.0060 (11)0.0055 (11)
C230.0325 (13)0.0270 (14)0.0243 (14)0.0045 (13)0.0076 (12)0.0066 (13)
C240.0343 (14)0.0282 (15)0.0248 (15)0.0058 (12)0.0070 (12)0.0067 (13)
C250.0398 (15)0.0281 (15)0.0296 (16)0.0006 (14)0.0072 (13)−0.0006 (14)
C260.0493 (16)0.0261 (15)0.0289 (16)0.0040 (14)0.0138 (13)0.0061 (13)
C270.0437 (16)0.0370 (17)0.0205 (15)0.0036 (14)0.0053 (12)0.0029 (14)
C280.0379 (13)0.0261 (14)0.0290 (14)0.0035 (14)0.0080 (11)0.0041 (14)
C290.0394 (16)0.0342 (16)0.0240 (16)0.0010 (13)0.0013 (13)0.0053 (13)
C300.0513 (19)0.076 (3)0.0222 (16)0.0061 (18)0.0056 (14)0.0009 (17)
C310.0544 (18)0.051 (2)0.0296 (16)−0.0086 (18)0.0019 (14)0.0020 (17)
C320.0548 (19)0.0315 (17)0.0286 (17)−0.0016 (15)0.0007 (15)0.0032 (14)
C330.108 (3)0.047 (2)0.0354 (19)−0.028 (2)0.005 (2)−0.0012 (18)
C340.057 (2)0.069 (3)0.073 (3)−0.021 (2)0.006 (2)−0.011 (2)

Geometric parameters (Å, °)

S1—C11.715 (3)S2—C181.719 (3)
S1—C41.719 (3)S2—C211.724 (3)
C1—C21.345 (5)C18—C191.345 (4)
C1—H10.9300C18—H180.9300
C2—C31.411 (5)C19—C201.415 (4)
C2—H20.9300C19—H190.9300
C3—C41.364 (4)C20—C211.368 (4)
C3—H30.9300C20—H200.9300
C4—C51.449 (4)C21—C221.445 (4)
C5—N11.264 (3)C22—N21.269 (4)
C5—H50.9300C22—H220.9300
N1—C61.427 (4)N2—C231.437 (4)
C6—C111.398 (4)C23—C241.398 (4)
C6—C71.419 (4)C23—C281.409 (4)
C7—C81.387 (5)C24—C251.385 (4)
C7—C121.515 (4)C24—C291.526 (4)
C8—C91.379 (5)C25—C261.393 (4)
C8—H80.9300C25—H250.9300
C9—C101.374 (5)C26—C271.381 (4)
C9—H90.9300C26—H260.9300
C10—C111.392 (5)C27—C281.395 (5)
C10—H100.9300C27—H270.9300
C11—C151.527 (4)C28—C321.517 (4)
C12—C141.498 (6)C29—C301.511 (5)
C12—C131.514 (5)C29—C311.518 (5)
C12—H120.9800C29—H290.9800
C13—H13A0.9600C30—H30A0.9600
C13—H13B0.9600C30—H30B0.9600
C13—H13C0.9600C30—H30C0.9600
C14—H14A0.9600C31—H31A0.9600
C14—H14B0.9600C31—H31B0.9600
C14—H14C0.9600C31—H31C0.9600
C15—C171.517 (5)C32—C331.519 (5)
C15—C161.533 (5)C32—C341.530 (5)
C15—H150.9800C32—H320.9800
C16—H16A0.9600C33—H33A0.9600
C16—H16B0.9600C33—H33B0.9600
C16—H16C0.9600C33—H33C0.9600
C17—H17A0.9600C34—H34A0.9600
C17—H17B0.9600C34—H34B0.9600
C17—H17C0.9600C34—H34C0.9600
C1—S1—C491.53 (16)C18—S2—C2191.46 (14)
C2—C1—S1111.8 (3)C19—C18—S2112.3 (2)
C2—C1—H1124.1C19—C18—H18123.8
S1—C1—H1124.1S2—C18—H18123.8
C1—C2—C3112.9 (3)C18—C19—C20112.3 (3)
C1—C2—H2123.6C18—C19—H19123.8
C3—C2—H2123.6C20—C19—H19123.8
C4—C3—C2112.8 (3)C21—C20—C19113.2 (3)
C4—C3—H3123.6C21—C20—H20123.4
C2—C3—H3123.6C19—C20—H20123.4
C3—C4—C5127.5 (3)C20—C21—C22127.3 (3)
C3—C4—S1111.0 (2)C20—C21—S2110.7 (2)
C5—C4—S1121.4 (2)C22—C21—S2121.9 (2)
N1—C5—C4122.0 (3)N2—C22—C21122.8 (3)
N1—C5—H5119.0N2—C22—H22118.6
C4—C5—H5119.0C21—C22—H22118.6
C5—N1—C6121.0 (3)C22—N2—C23117.8 (2)
C11—C6—C7121.0 (3)C24—C23—C28121.8 (3)
C11—C6—N1120.6 (2)C24—C23—N2119.5 (2)
C7—C6—N1118.1 (2)C28—C23—N2118.6 (3)
C8—C7—C6117.9 (3)C25—C24—C23118.1 (3)
C8—C7—C12120.4 (2)C25—C24—C29120.8 (3)
C6—C7—C12121.7 (3)C23—C24—C29120.8 (3)
C9—C8—C7121.8 (3)C24—C25—C26121.3 (3)
C9—C8—H8119.1C24—C25—H25119.3
C7—C8—H8119.1C26—C25—H25119.3
C10—C9—C8119.2 (3)C27—C26—C25119.6 (3)
C10—C9—H9120.4C27—C26—H26120.2
C8—C9—H9120.4C25—C26—H26120.2
C9—C10—C11122.2 (3)C26—C27—C28121.3 (3)
C9—C10—H10118.9C26—C27—H27119.3
C11—C10—H10118.9C28—C27—H27119.3
C10—C11—C6117.9 (3)C27—C28—C23117.7 (3)
C10—C11—C15119.4 (3)C27—C28—C32121.5 (3)
C6—C11—C15122.7 (3)C23—C28—C32120.8 (3)
C14—C12—C7110.2 (3)C30—C29—C31110.7 (3)
C14—C12—C13110.3 (4)C30—C29—C24109.5 (2)
C7—C12—C13111.6 (3)C31—C29—C24114.1 (3)
C14—C12—H12108.2C30—C29—H29107.4
C7—C12—H12108.2C31—C29—H29107.4
C13—C12—H12108.2C24—C29—H29107.4
C12—C13—H13A109.5C29—C30—H30A109.5
C12—C13—H13B109.5C29—C30—H30B109.5
H13A—C13—H13B109.5H30A—C30—H30B109.5
C12—C13—H13C109.5C29—C30—H30C109.5
H13A—C13—H13C109.5H30A—C30—H30C109.5
H13B—C13—H13C109.5H30B—C30—H30C109.5
C12—C14—H14A109.5C29—C31—H31A109.5
C12—C14—H14B109.5C29—C31—H31B109.5
H14A—C14—H14B109.5H31A—C31—H31B109.5
C12—C14—H14C109.5C29—C31—H31C109.5
H14A—C14—H14C109.5H31A—C31—H31C109.5
H14B—C14—H14C109.5H31B—C31—H31C109.5
C17—C15—C11110.4 (3)C28—C32—C33113.5 (3)
C17—C15—C16110.7 (3)C28—C32—C34110.4 (3)
C11—C15—C16111.2 (3)C33—C32—C34110.6 (3)
C17—C15—H15108.1C28—C32—H32107.4
C11—C15—H15108.1C33—C32—H32107.4
C16—C15—H15108.1C34—C32—H32107.4
C15—C16—H16A109.5C32—C33—H33A109.5
C15—C16—H16B109.5C32—C33—H33B109.5
H16A—C16—H16B109.5H33A—C33—H33B109.5
C15—C16—H16C109.5C32—C33—H33C109.5
H16A—C16—H16C109.5H33A—C33—H33C109.5
H16B—C16—H16C109.5H33B—C33—H33C109.5
C15—C17—H17A109.5C32—C34—H34A109.5
C15—C17—H17B109.5C32—C34—H34B109.5
H17A—C17—H17B109.5H34A—C34—H34B109.5
C15—C17—H17C109.5C32—C34—H34C109.5
H17A—C17—H17C109.5H34A—C34—H34C109.5
H17B—C17—H17C109.5H34B—C34—H34C109.5
C4—S1—C1—C20.4 (3)C21—S2—C18—C190.1 (2)
S1—C1—C2—C3−0.2 (4)S2—C18—C19—C200.3 (3)
C1—C2—C3—C4−0.2 (4)C18—C19—C20—C21−0.5 (4)
C2—C3—C4—C5−176.0 (3)C19—C20—C21—C22−177.2 (3)
C2—C3—C4—S10.5 (3)C19—C20—C21—S20.6 (3)
C1—S1—C4—C3−0.5 (2)C18—S2—C21—C20−0.4 (2)
C1—S1—C4—C5176.2 (2)C18—S2—C21—C22177.6 (2)
C3—C4—C5—N1173.4 (3)C20—C21—C22—N2176.8 (3)
S1—C4—C5—N1−2.8 (4)S2—C21—C22—N2−0.8 (4)
C4—C5—N1—C6−177.8 (2)C21—C22—N2—C23−177.7 (2)
C5—N1—C6—C1184.0 (3)C22—N2—C23—C2488.5 (3)
C5—N1—C6—C7−102.3 (3)C22—N2—C23—C28−94.9 (3)
C11—C6—C7—C80.1 (4)C28—C23—C24—C253.0 (4)
N1—C6—C7—C8−173.5 (3)N2—C23—C24—C25179.5 (2)
C11—C6—C7—C12−178.7 (3)C28—C23—C24—C29−172.0 (3)
N1—C6—C7—C127.6 (4)N2—C23—C24—C294.5 (4)
C6—C7—C8—C91.0 (5)C23—C24—C25—C26−1.7 (4)
C12—C7—C8—C9179.9 (3)C29—C24—C25—C26173.2 (3)
C7—C8—C9—C10−0.5 (5)C24—C25—C26—C27−0.8 (4)
C8—C9—C10—C11−1.4 (6)C25—C26—C27—C282.2 (4)
C9—C10—C11—C62.5 (5)C26—C27—C28—C23−0.9 (4)
C9—C10—C11—C15179.1 (3)C26—C27—C28—C32−178.1 (3)
C7—C6—C11—C10−1.8 (4)C24—C23—C28—C27−1.7 (4)
N1—C6—C11—C10171.7 (3)N2—C23—C28—C27−178.2 (3)
C7—C6—C11—C15−178.3 (3)C24—C23—C28—C32175.5 (3)
N1—C6—C11—C15−4.8 (5)N2—C23—C28—C32−1.0 (4)
C8—C7—C12—C14−67.3 (4)C25—C24—C29—C30−97.0 (3)
C6—C7—C12—C14111.6 (4)C23—C24—C29—C3077.8 (4)
C8—C7—C12—C1355.6 (5)C25—C24—C29—C3127.7 (4)
C6—C7—C12—C13−125.6 (4)C23—C24—C29—C31−157.5 (3)
C10—C11—C15—C17−72.7 (4)C27—C28—C32—C33−23.4 (5)
C6—C11—C15—C17103.7 (4)C23—C28—C32—C33159.5 (3)
C10—C11—C15—C1650.5 (4)C27—C28—C32—C34101.4 (4)
C6—C11—C15—C16−133.1 (3)C23—C28—C32—C34−75.7 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C20—H20···N10.932.523.449 (8)178

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2882).

References

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