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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2458.
Published online 2008 November 26. doi:  10.1107/S1600536808038890
PMCID: PMC2960062

10-Hexyl-10H-phenothia­zine-3-carbaldehyde

Abstract

The asymmetric unit of the title compound, C19H21NOS, contains two mol­ecules, which form dimers via pairs of weak C—H(...)O hydrogen bonds.

Related literature

For the synthesis, see: Krishna et al. (1999 [triangle]). For general background, see: Hauck et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2458-scheme1.jpg

Experimental

Crystal data

  • C19H21NOS
  • M r = 311.43
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2458-efi1.jpg
  • a = 8.4073 (9) Å
  • b = 13.7719 (15) Å
  • c = 14.6485 (15) Å
  • α = 93.957 (2)°
  • β = 98.781 (2)°
  • γ = 90.983 (2)°
  • V = 1671.5 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.20 mm−1
  • T = 298 (2) K
  • 0.23 × 0.20 × 0.10 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1997 [triangle]) T min = 0.957, T max = 0.981
  • 9878 measured reflections
  • 5800 independent reflections
  • 3575 reflections with I > 2σ(I)
  • R int = 0.089

Refinement

  • R[F 2 > 2σ(F 2)] = 0.079
  • wR(F 2) = 0.210
  • S = 0.96
  • 5800 reflections
  • 399 parameters
  • H-atom parameters constrained
  • Δρmax = 0.35 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038890/hb2847sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038890/hb2847Isup2.hkl

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

supplementary crystallographic information

Comment

We used the Vilsmeier reaction to obtain the title compound, (I), which is a good intermediate for several compounds (Hauck et al., 2007).

The asymmetric unit of (I) contains two molecules (Fig. 1), which form dimers via pairs of weak C—H···O bonds (Table 1).

Experimental

The title material, prepared by a literature method (Krishna et al. 1999), was collected by filtration and recrystallized from chloroform as yellow blocks of (I).

Refinement

The H atoms were geometrically placed (C—H = 0.93-0.97Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Figures

Fig. 1.
The molecular structure of (I) showing 50% displacement ellipsoids for the non-hydrogen atoms. The hydrogen bonds are indicated by dashed lines.

Crystal data

C19H21NOSZ = 4
Mr = 311.43F000 = 664
Triclinic, P1Dx = 1.238 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 8.4073 (9) ÅCell parameters from 2010 reflections
b = 13.7719 (15) Åθ = 2.5–21.1º
c = 14.6485 (15) ŵ = 0.20 mm1
α = 93.957 (2)ºT = 298 (2) K
β = 98.781 (2)ºBlock, yellow
γ = 90.983 (2)º0.23 × 0.20 × 0.10 mm
V = 1671.5 (3) Å3

Data collection

Bruker SMART CCD diffractometer5800 independent reflections
Radiation source: fine-focus sealed tube3575 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.089
T = 298(2) Kθmax = 25.0º
ω scansθmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1997)h = −9→9
Tmin = 0.957, Tmax = 0.981k = −16→16
9878 measured reflectionsl = −17→10

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.079H-atom parameters constrained
wR(F2) = 0.210  w = 1/[σ2(Fo2) + (0.0951P)2 + 0.4339P] where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max = 0.008
5800 reflectionsΔρmax = 0.35 e Å3
399 parametersΔρmin = −0.26 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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 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
C10.8046 (4)−0.0018 (3)1.0692 (3)0.0498 (9)
C20.7545 (5)−0.0942 (3)1.0280 (3)0.0614 (11)
H20.7849−0.14901.05940.074*
C30.6625 (5)−0.1058 (3)0.9428 (3)0.0633 (11)
H30.6285−0.16810.91830.076*
C40.6185 (5)−0.0276 (3)0.8922 (3)0.0575 (10)
C50.6693 (5)0.0642 (3)0.9305 (3)0.0562 (10)
H50.64310.11790.89650.067*
C60.7571 (5)0.0781 (3)1.0172 (3)0.0556 (10)
C70.5184 (5)−0.0421 (3)0.8011 (3)0.0695 (12)
H70.4809−0.10520.78200.083*
C80.9599 (5)0.1833 (3)1.1502 (3)0.0537 (10)
C91.0577 (5)0.2649 (3)1.1820 (3)0.0638 (11)
H91.03960.32271.15320.077*
C101.1795 (6)0.2617 (3)1.2545 (3)0.0707 (12)
H101.24270.31701.27640.085*
C111.2069 (5)0.1751 (4)1.2945 (3)0.0737 (12)
H111.28960.17211.34420.088*
C121.1154 (5)0.0931 (3)1.2629 (3)0.0624 (11)
H121.13860.03521.29070.075*
C130.9881 (5)0.0945 (3)1.1901 (3)0.0518 (9)
C140.8990 (5)−0.0712 (3)1.2169 (3)0.0569 (10)
H14A0.7963−0.10651.20380.068*
H14B0.9123−0.04551.28100.068*
C151.0314 (5)−0.1438 (3)1.2071 (3)0.0620 (11)
H15A1.0262−0.16681.14260.074*
H15B1.1359−0.11231.22790.074*
C161.0099 (5)−0.2288 (3)1.2645 (3)0.0658 (11)
H16A1.0017−0.20331.32700.079*
H16B0.9084−0.26211.23940.079*
C171.1389 (5)−0.3018 (3)1.2700 (4)0.0755 (13)
H17A1.2404−0.26971.29710.091*
H17B1.1493−0.32691.20770.091*
C181.1080 (7)−0.3864 (4)1.3264 (5)0.112 (2)
H18A1.0881−0.35941.38640.134*
H18B1.0090−0.41941.29630.134*
C191.2236 (9)−0.4567 (5)1.3419 (6)0.152 (3)
H19A1.2557−0.47931.28420.229*
H19B1.1795−0.51041.36930.229*
H19C1.3155−0.42911.38310.229*
C200.7245 (5)0.5290 (3)0.9780 (3)0.0549 (10)
C210.6665 (5)0.4380 (3)0.9407 (3)0.0553 (10)
H210.71150.38310.96660.066*
C220.5447 (4)0.4260 (3)0.8668 (3)0.0509 (9)
C230.4783 (4)0.5078 (3)0.8231 (3)0.0511 (9)
C240.5365 (5)0.5994 (3)0.8624 (3)0.0593 (10)
H240.49360.65500.83680.071*
C250.6555 (5)0.6090 (3)0.9380 (3)0.0617 (11)
H250.69060.67100.96290.074*
C260.8506 (6)0.5412 (3)1.0586 (3)0.0705 (12)
H260.88610.60441.07920.085*
C270.3997 (4)0.3210 (3)0.7143 (3)0.0537 (9)
C280.3913 (5)0.2390 (3)0.6537 (3)0.0658 (11)
H280.42920.18050.67540.079*
C290.3283 (6)0.2428 (4)0.5627 (3)0.0823 (14)
H290.32150.18720.52250.099*
C300.2749 (6)0.3302 (4)0.5313 (3)0.0829 (14)
H300.22940.33290.46950.099*
C310.2877 (5)0.4140 (3)0.5896 (3)0.0708 (12)
H310.25490.47280.56640.085*
C320.3497 (4)0.4110 (3)0.6834 (3)0.0548 (10)
C330.2671 (5)0.5804 (3)0.7159 (3)0.0574 (10)
H33A0.24570.61740.77130.069*
H33B0.16410.55700.68170.069*
C340.3427 (5)0.6498 (3)0.6567 (3)0.0663 (11)
H34A0.44030.67960.69210.080*
H34B0.37160.61350.60280.080*
C350.2280 (5)0.7279 (3)0.6258 (3)0.0703 (12)
H35A0.19470.76080.68020.084*
H35B0.13270.69720.58860.084*
C360.2949 (5)0.8034 (3)0.5705 (3)0.0719 (12)
H36A0.39060.83380.60740.086*
H36B0.32710.77070.51570.086*
C370.1802 (7)0.8810 (4)0.5411 (4)0.0952 (16)
H37A0.08590.85090.50240.114*
H37B0.14530.91250.59570.114*
C380.2490 (8)0.9569 (4)0.4890 (5)0.130 (2)
H38A0.34140.98810.52710.195*
H38B0.16941.00450.47300.195*
H38C0.28040.92690.43360.195*
N10.8901 (4)0.0114 (2)1.1586 (2)0.0562 (8)
N20.3601 (4)0.4957 (2)0.7446 (2)0.0557 (8)
O10.4801 (4)0.0199 (2)0.7486 (2)0.0933 (11)
O20.9125 (4)0.4760 (2)1.1007 (2)0.0861 (10)
S10.79048 (15)0.19795 (7)1.06651 (8)0.0734 (4)
S20.45941 (13)0.30926 (7)0.83359 (7)0.0617 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.053 (2)0.050 (2)0.048 (2)0.0123 (17)0.0076 (18)0.0108 (17)
C20.064 (3)0.048 (2)0.071 (3)0.0074 (18)0.003 (2)0.013 (2)
C30.067 (3)0.050 (2)0.069 (3)0.0088 (19)−0.001 (2)0.000 (2)
C40.054 (2)0.057 (2)0.061 (3)0.0105 (18)0.007 (2)0.004 (2)
C50.061 (2)0.058 (2)0.052 (2)0.0141 (19)0.009 (2)0.0121 (19)
C60.060 (2)0.048 (2)0.062 (3)0.0103 (17)0.013 (2)0.0098 (19)
C70.061 (3)0.073 (3)0.071 (3)0.009 (2)0.002 (2)−0.002 (2)
C80.061 (2)0.051 (2)0.051 (2)0.0096 (18)0.0128 (19)0.0030 (18)
C90.075 (3)0.056 (2)0.062 (3)0.002 (2)0.018 (2)0.002 (2)
C100.073 (3)0.074 (3)0.061 (3)−0.006 (2)0.010 (2)−0.011 (2)
C110.066 (3)0.089 (3)0.063 (3)0.007 (2)0.001 (2)−0.006 (3)
C120.070 (3)0.072 (3)0.045 (2)0.009 (2)0.005 (2)0.006 (2)
C130.057 (2)0.057 (2)0.044 (2)0.0081 (18)0.0135 (18)0.0017 (18)
C140.068 (3)0.059 (2)0.047 (2)0.0095 (19)0.0128 (19)0.0161 (18)
C150.067 (3)0.061 (2)0.060 (3)0.012 (2)0.009 (2)0.019 (2)
C160.063 (3)0.063 (3)0.074 (3)0.003 (2)0.010 (2)0.020 (2)
C170.061 (3)0.068 (3)0.096 (4)0.004 (2)−0.001 (2)0.020 (2)
C180.096 (4)0.070 (3)0.173 (6)0.009 (3)0.020 (4)0.045 (4)
C190.144 (6)0.135 (5)0.194 (8)0.033 (5)0.035 (6)0.094 (5)
C200.061 (2)0.055 (2)0.051 (2)0.0059 (18)0.011 (2)0.0107 (19)
C210.062 (2)0.051 (2)0.059 (3)0.0127 (18)0.019 (2)0.0158 (19)
C220.053 (2)0.053 (2)0.050 (2)0.0100 (17)0.0137 (19)0.0118 (18)
C230.056 (2)0.050 (2)0.052 (2)0.0131 (17)0.0175 (19)0.0101 (18)
C240.076 (3)0.046 (2)0.057 (3)0.0092 (19)0.009 (2)0.0109 (19)
C250.083 (3)0.047 (2)0.057 (3)0.001 (2)0.019 (2)0.0037 (19)
C260.078 (3)0.071 (3)0.064 (3)0.004 (2)0.014 (2)0.001 (2)
C270.054 (2)0.055 (2)0.053 (2)−0.0017 (18)0.0077 (18)0.0091 (19)
C280.073 (3)0.057 (2)0.069 (3)0.003 (2)0.017 (2)0.005 (2)
C290.103 (4)0.078 (3)0.065 (3)0.001 (3)0.017 (3)−0.008 (3)
C300.100 (4)0.093 (4)0.051 (3)0.001 (3)0.001 (3)−0.001 (3)
C310.083 (3)0.074 (3)0.055 (3)0.012 (2)0.004 (2)0.015 (2)
C320.053 (2)0.057 (2)0.057 (3)0.0070 (18)0.0142 (19)0.0111 (19)
C330.056 (2)0.056 (2)0.062 (3)0.0153 (18)0.0077 (19)0.0164 (19)
C340.063 (3)0.066 (3)0.071 (3)0.011 (2)0.004 (2)0.021 (2)
C350.075 (3)0.073 (3)0.066 (3)0.019 (2)0.012 (2)0.023 (2)
C360.082 (3)0.067 (3)0.066 (3)0.008 (2)0.000 (2)0.020 (2)
C370.116 (4)0.085 (3)0.088 (4)0.030 (3)0.013 (3)0.031 (3)
C380.163 (7)0.093 (4)0.135 (6)0.005 (4)0.002 (5)0.060 (4)
N10.067 (2)0.0476 (18)0.055 (2)0.0072 (15)0.0071 (17)0.0155 (15)
N20.062 (2)0.0523 (18)0.054 (2)0.0137 (15)0.0071 (17)0.0119 (15)
O10.108 (3)0.092 (2)0.074 (2)0.028 (2)−0.0122 (19)0.0163 (19)
O20.086 (2)0.096 (2)0.073 (2)0.0149 (18)−0.0069 (18)0.0213 (18)
S10.0895 (9)0.0463 (6)0.0770 (8)0.0153 (5)−0.0129 (6)0.0065 (5)
S20.0761 (7)0.0494 (6)0.0601 (7)−0.0003 (5)0.0070 (5)0.0159 (5)

Geometric parameters (Å, °)

C1—N11.393 (5)C20—C211.383 (5)
C1—C21.400 (5)C20—C261.460 (6)
C1—C61.411 (5)C21—C221.371 (5)
C2—C31.362 (5)C21—H210.9300
C2—H20.9300C22—C231.415 (5)
C3—C41.373 (5)C22—S21.755 (4)
C3—H30.9300C23—N21.397 (5)
C4—C51.380 (5)C23—C241.399 (5)
C4—C71.464 (6)C24—C251.372 (6)
C5—C61.367 (5)C24—H240.9300
C5—H50.9300C25—H250.9300
C6—S11.756 (4)C26—O21.204 (5)
C7—O11.203 (5)C26—H260.9300
C7—H70.9300C27—C281.381 (5)
C8—C91.392 (5)C27—C321.398 (5)
C8—C131.400 (5)C27—S21.763 (4)
C8—S11.756 (4)C28—C291.362 (6)
C9—C101.362 (6)C28—H280.9300
C9—H90.9300C29—C301.376 (6)
C10—C111.373 (6)C29—H290.9300
C10—H100.9300C30—C311.381 (6)
C11—C121.368 (6)C30—H300.9300
C11—H110.9300C31—C321.396 (6)
C12—C131.392 (5)C31—H310.9300
C12—H120.9300C32—N21.415 (5)
C13—N11.407 (5)C33—N21.466 (4)
C14—N11.464 (4)C33—C341.528 (5)
C14—C151.526 (5)C33—H33A0.9700
C14—H14A0.9700C33—H33B0.9700
C14—H14B0.9700C34—C351.504 (5)
C15—C161.511 (5)C34—H34A0.9700
C15—H15A0.9700C34—H34B0.9700
C15—H15B0.9700C35—C361.513 (6)
C16—C171.489 (5)C35—H35A0.9700
C16—H16A0.9700C35—H35B0.9700
C16—H16B0.9700C36—C371.494 (6)
C17—C181.515 (6)C36—H36A0.9700
C17—H17A0.9700C36—H36B0.9700
C17—H17B0.9700C37—C381.494 (7)
C18—C191.389 (7)C37—H37A0.9700
C18—H18A0.9700C37—H37B0.9700
C18—H18B0.9700C38—H38A0.9600
C19—H19A0.9600C38—H38B0.9600
C19—H19B0.9600C38—H38C0.9600
C19—H19C0.9600S1—S24.4392 (15)
C20—C251.378 (5)
N1—C1—C2122.1 (3)C21—C22—C23120.4 (3)
N1—C1—C6121.4 (3)C21—C22—S2119.3 (3)
C2—C1—C6116.4 (4)C23—C22—S2120.1 (3)
C3—C2—C1121.5 (4)N2—C23—C24122.7 (3)
C3—C2—H2119.2N2—C23—C22120.6 (3)
C1—C2—H2119.2C24—C23—C22116.7 (4)
C2—C3—C4121.6 (4)C25—C24—C23121.4 (4)
C2—C3—H3119.2C25—C24—H24119.3
C4—C3—H3119.2C23—C24—H24119.3
C3—C4—C5118.0 (4)C24—C25—C20121.7 (4)
C3—C4—C7120.4 (4)C24—C25—H25119.2
C5—C4—C7121.5 (4)C20—C25—H25119.2
C6—C5—C4121.5 (4)O2—C26—C20125.3 (4)
C6—C5—H5119.2O2—C26—H26117.4
C4—C5—H5119.2C20—C26—H26117.4
C5—C6—C1120.8 (4)C28—C27—C32121.1 (4)
C5—C6—S1118.0 (3)C28—C27—S2119.0 (3)
C1—C6—S1120.8 (3)C32—C27—S2119.7 (3)
O1—C7—C4126.3 (4)C29—C28—C27120.8 (4)
O1—C7—H7116.9C29—C28—H28119.6
C4—C7—H7116.9C27—C28—H28119.6
C9—C8—C13120.5 (4)C28—C29—C30119.1 (4)
C9—C8—S1118.0 (3)C28—C29—H29120.5
C13—C8—S1121.2 (3)C30—C29—H29120.5
C10—C9—C8121.2 (4)C29—C30—C31121.2 (5)
C10—C9—H9119.4C29—C30—H30119.4
C8—C9—H9119.4C31—C30—H30119.4
C9—C10—C11118.5 (4)C30—C31—C32120.4 (4)
C9—C10—H10120.7C30—C31—H31119.8
C11—C10—H10120.7C32—C31—H31119.8
C12—C11—C10121.4 (4)C31—C32—C27117.4 (4)
C12—C11—H11119.3C31—C32—N2121.1 (3)
C10—C11—H11119.3C27—C32—N2121.5 (4)
C11—C12—C13121.4 (4)N2—C33—C34117.0 (3)
C11—C12—H12119.3N2—C33—H33A108.0
C13—C12—H12119.3C34—C33—H33A108.0
C12—C13—C8116.9 (4)N2—C33—H33B108.0
C12—C13—N1122.0 (3)C34—C33—H33B108.0
C8—C13—N1121.1 (3)H33A—C33—H33B107.3
N1—C14—C15117.3 (3)C35—C34—C33110.9 (3)
N1—C14—H14A108.0C35—C34—H34A109.4
C15—C14—H14A108.0C33—C34—H34A109.5
N1—C14—H14B108.0C35—C34—H34B109.5
C15—C14—H14B108.0C33—C34—H34B109.5
H14A—C14—H14B107.2H34A—C34—H34B108.0
C16—C15—C14109.5 (3)C34—C35—C36115.0 (4)
C16—C15—H15A109.8C34—C35—H35A108.5
C14—C15—H15A109.8C36—C35—H35A108.5
C16—C15—H15B109.8C34—C35—H35B108.5
C14—C15—H15B109.8C36—C35—H35B108.5
H15A—C15—H15B108.2H35A—C35—H35B107.5
C17—C16—C15116.2 (4)C37—C36—C35114.4 (4)
C17—C16—H16A108.2C37—C36—H36A108.7
C15—C16—H16A108.2C35—C36—H36A108.6
C17—C16—H16B108.2C37—C36—H36B108.7
C15—C16—H16B108.2C35—C36—H36B108.7
H16A—C16—H16B107.4H36A—C36—H36B107.6
C16—C17—C18113.6 (4)C38—C37—C36114.0 (5)
C16—C17—H17A108.9C38—C37—H37A108.7
C18—C17—H17A108.9C36—C37—H37A108.7
C16—C17—H17B108.8C38—C37—H37B108.7
C18—C17—H17B108.8C36—C37—H37B108.8
H17A—C17—H17B107.7H37A—C37—H37B107.6
C19—C18—C17119.6 (5)C37—C38—H38A109.5
C19—C18—H18A107.4C37—C38—H38B109.5
C17—C18—H18A107.4H38A—C38—H38B109.5
C19—C18—H18B107.5C37—C38—H38C109.5
C17—C18—H18B107.4H38A—C38—H38C109.5
H18A—C18—H18B107.0H38B—C38—H38C109.5
C18—C19—H19A109.4C1—N1—C13122.9 (3)
C18—C19—H19B109.5C1—N1—C14118.1 (3)
H19A—C19—H19B109.5C13—N1—C14118.2 (3)
C18—C19—H19C109.5C23—N2—C32121.6 (3)
H19A—C19—H19C109.5C23—N2—C33118.3 (3)
H19B—C19—H19C109.5C32—N2—C33119.0 (3)
C25—C20—C21117.6 (4)C8—S1—C6100.72 (18)
C25—C20—C26120.6 (4)C8—S1—S2162.13 (14)
C21—C20—C26121.8 (4)C6—S1—S290.88 (14)
C22—C21—C20122.2 (3)C27—S2—C2299.68 (18)
C22—C21—H21118.9C27—S2—S1151.06 (13)
C20—C21—H21118.9C22—S2—S188.34 (13)
N1—C1—C2—C3175.9 (4)C30—C31—C32—C271.1 (6)
C6—C1—C2—C3−1.2 (6)C30—C31—C32—N2−178.5 (4)
C1—C2—C3—C42.0 (6)C28—C27—C32—C311.4 (6)
C2—C3—C4—C5−0.5 (6)S2—C27—C32—C31−173.4 (3)
C2—C3—C4—C7−179.6 (4)C28—C27—C32—N2−179.0 (4)
C3—C4—C5—C6−1.8 (6)S2—C27—C32—N26.1 (5)
C7—C4—C5—C6177.3 (4)N2—C33—C34—C35175.1 (4)
C4—C5—C6—C12.6 (6)C33—C34—C35—C36177.1 (4)
C4—C5—C6—S1−170.7 (3)C34—C35—C36—C37−179.4 (4)
N1—C1—C6—C5−178.2 (3)C35—C36—C37—C38178.2 (5)
C2—C1—C6—C5−1.1 (5)C2—C1—N1—C13157.4 (4)
N1—C1—C6—S1−5.0 (5)C6—C1—N1—C13−25.7 (5)
C2—C1—C6—S1172.1 (3)C2—C1—N1—C14−12.5 (5)
C3—C4—C7—O1−175.6 (4)C6—C1—N1—C14164.4 (3)
C5—C4—C7—O15.4 (7)C12—C13—N1—C1−155.8 (4)
C13—C8—C9—C10−2.3 (6)C8—C13—N1—C125.3 (5)
S1—C8—C9—C10172.0 (3)C12—C13—N1—C1414.1 (5)
C8—C9—C10—C111.6 (6)C8—C13—N1—C14−164.8 (3)
C9—C10—C11—C120.2 (7)C15—C14—N1—C185.4 (4)
C10—C11—C12—C13−1.5 (6)C15—C14—N1—C13−85.0 (4)
C11—C12—C13—C80.8 (6)C24—C23—N2—C32152.8 (4)
C11—C12—C13—N1−178.2 (4)C22—C23—N2—C32−27.4 (5)
C9—C8—C13—C121.0 (5)C24—C23—N2—C33−14.9 (5)
S1—C8—C13—C12−173.1 (3)C22—C23—N2—C33164.9 (3)
C9—C8—C13—N1−180.0 (3)C31—C32—N2—C23−151.2 (4)
S1—C8—C13—N15.9 (5)C27—C32—N2—C2329.2 (5)
N1—C14—C15—C16−173.9 (3)C31—C32—N2—C3316.4 (5)
C14—C15—C16—C17−174.2 (4)C27—C32—N2—C33−163.1 (3)
C15—C16—C17—C18−178.5 (4)C34—C33—N2—C2383.5 (4)
C16—C17—C18—C19−176.0 (6)C34—C33—N2—C32−84.5 (4)
C25—C20—C21—C22−0.1 (6)C9—C8—S1—C6157.7 (3)
C26—C20—C21—C22178.0 (4)C13—C8—S1—C6−28.0 (3)
C20—C21—C22—C232.8 (6)C9—C8—S1—S228.0 (6)
C20—C21—C22—S2−171.3 (3)C13—C8—S1—S2−157.7 (3)
C21—C22—C23—N2176.6 (3)C5—C6—S1—C8−159.1 (3)
S2—C22—C23—N2−9.3 (5)C1—C6—S1—C827.6 (4)
C21—C22—C23—C24−3.6 (5)C5—C6—S1—S27.2 (3)
S2—C22—C23—C24170.5 (3)C1—C6—S1—S2−166.1 (3)
N2—C23—C24—C25−178.3 (4)C28—C27—S2—C22152.0 (3)
C22—C23—C24—C251.9 (6)C32—C27—S2—C22−33.1 (3)
C23—C24—C25—C200.7 (6)C28—C27—S2—S147.6 (5)
C21—C20—C25—C24−1.6 (6)C32—C27—S2—S1−137.4 (3)
C26—C20—C25—C24−179.8 (4)C21—C22—S2—C27−151.1 (3)
C25—C20—C26—O2176.4 (4)C23—C22—S2—C2734.8 (3)
C21—C20—C26—O2−1.7 (7)C21—C22—S2—S10.9 (3)
C32—C27—C28—C29−2.5 (6)C23—C22—S2—S1−173.2 (3)
S2—C27—C28—C29172.4 (4)C8—S1—S2—C2775.2 (5)
C27—C28—C29—C301.0 (7)C6—S1—S2—C27−55.7 (3)
C28—C29—C30—C311.6 (8)C8—S1—S2—C22−32.0 (4)
C29—C30—C31—C32−2.6 (7)C6—S1—S2—C22−162.86 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C28—H28···O10.932.543.454 (5)168
C9—H9···O20.932.503.394 (5)162

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2847).

References

  • Bruker (2000). SMART and SAINT Bruker AXS Inc.,Madison, Wisconsin, USA.
  • Hauck, M., Schönhaber, J., Zucchero, A. J., Hardcastle, K. I., Müller, T. J. J. & Bunz, U. H. F. (2007). J. Org. Chem.72, 6714–6725. [PubMed]
  • Krishna, R. M., Kurshev, V. & Kervan, L. (1999). Phys. Chem. Chem. Phys.11, 2833–2840.
  • Sheldrick, G. M. (1997). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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