organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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COMMUNICATIONS
ISSN: 2056-9890

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

aDepartment of Chemistry, Central China Normal University, Wuhan, Hubei 430079, People's Republic of China
*Correspondence e-mail: hlwang@mail.ccnu.edu.cn

(Received 14 November 2008; accepted 20 November 2008; online 26 November 2008)

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[Krishna, R. M., Kurshev, V. & Kervan, L. (1999). Phys. Chem. Chem. Phys. 11, 2833-2840.]). For general background, see: Hauck et al. (2007[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.]).

[Scheme 1]

Experimental

Crystal data
  • C19H21NOS

  • Mr = 311.43

  • Triclinic, [P \overline 1]

  • 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[Sheldrick, G. M. (1997). SADABS. University of Göttingen, Germany.]) Tmin = 0.957, Tmax = 0.981

  • 9878 measured reflections

  • 5800 independent reflections

  • 3575 reflections with I > 2σ(I)

  • Rint = 0.089

Refinement
  • R[F2 > 2σ(F2)] = 0.079

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C28—H28⋯O1 0.93 2.54 3.454 (5) 168
C9—H9⋯O2 0.93 2.50 3.394 (5) 162

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc.,Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc.,Madison, Wisconsin, USA.])'; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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).

Related literature top

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

Experimental top

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 top

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).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000)'; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 50% displacement ellipsoids for the non-hydrogen atoms. The hydrogen bonds are indicated by dashed lines.
10-Hexyl-10H-phenothiazine-3-carbaldehyde top
Crystal data top
C19H21NOSZ = 4
Mr = 311.43F(000) = 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 = 2.5–21.1°
c = 14.6485 (15) ŵ = 0.20 mm1
α = 93.957 (2)°T = 298 K
β = 98.781 (2)°Block, yellow
γ = 90.983 (2)°0.23 × 0.20 × 0.10 mm
V = 1671.5 (3) Å3
Data collection top
Bruker SMART CCD
diffractometer
5800 independent reflections
Radiation source: fine-focus sealed tube3575 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.089
ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
h = 99
Tmin = 0.957, Tmax = 0.981k = 1616
9878 measured reflectionsl = 1710
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.079Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.210H-atom parameters constrained
S = 0.96 w = 1/[σ2(Fo2) + (0.0951P)2 + 0.4339P]
where P = (Fo2 + 2Fc2)/3
5800 reflections(Δ/σ)max = 0.008
399 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C19H21NOSγ = 90.983 (2)°
Mr = 311.43V = 1671.5 (3) Å3
Triclinic, P1Z = 4
a = 8.4073 (9) ÅMo Kα radiation
b = 13.7719 (15) ŵ = 0.20 mm1
c = 14.6485 (15) ÅT = 298 K
α = 93.957 (2)°0.23 × 0.20 × 0.10 mm
β = 98.781 (2)°
Data collection top
Bruker SMART CCD
diffractometer
5800 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
3575 reflections with I > 2σ(I)
Tmin = 0.957, Tmax = 0.981Rint = 0.089
9878 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0790 restraints
wR(F2) = 0.210H-atom parameters constrained
S = 0.96Δρmax = 0.35 e Å3
5800 reflectionsΔρmin = 0.27 e Å3
399 parameters
Special details top

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) top
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)
H20.78490.14901.05940.074*
C30.6625 (5)0.1058 (3)0.9428 (3)0.0633 (11)
H30.62850.16810.91830.076*
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)
H70.48090.10520.78200.083*
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)
H14A0.79630.10651.20380.068*
H14B0.91230.04551.28100.068*
C151.0314 (5)0.1438 (3)1.2071 (3)0.0620 (11)
H15A1.02620.16681.14260.074*
H15B1.13590.11231.22790.074*
C161.0099 (5)0.2288 (3)1.2645 (3)0.0658 (11)
H16A1.00170.20331.32700.079*
H16B0.90840.26211.23940.079*
C171.1389 (5)0.3018 (3)1.2700 (4)0.0755 (13)
H17A1.24040.26971.29710.091*
H17B1.14930.32691.20770.091*
C181.1080 (7)0.3864 (4)1.3264 (5)0.112 (2)
H18A1.08810.35941.38640.134*
H18B1.00900.41941.29630.134*
C191.2236 (9)0.4567 (5)1.3419 (6)0.152 (3)
H19A1.25570.47931.28420.229*
H19B1.17950.51041.36930.229*
H19C1.31550.42911.38310.229*
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) top
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, º) top
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—C31.2 (6)C30—C31—C32—N2178.5 (4)
C1—C2—C3—C42.0 (6)C28—C27—C32—C311.4 (6)
C2—C3—C4—C50.5 (6)S2—C27—C32—C31173.4 (3)
C2—C3—C4—C7179.6 (4)C28—C27—C32—N2179.0 (4)
C3—C4—C5—C61.8 (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—S1170.7 (3)C34—C35—C36—C37179.4 (4)
N1—C1—C6—C5178.2 (3)C35—C36—C37—C38178.2 (5)
C2—C1—C6—C51.1 (5)C2—C1—N1—C13157.4 (4)
N1—C1—C6—S15.0 (5)C6—C1—N1—C1325.7 (5)
C2—C1—C6—S1172.1 (3)C2—C1—N1—C1412.5 (5)
C3—C4—C7—O1175.6 (4)C6—C1—N1—C14164.4 (3)
C5—C4—C7—O15.4 (7)C12—C13—N1—C1155.8 (4)
C13—C8—C9—C102.3 (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—C14164.8 (3)
C9—C10—C11—C120.2 (7)C15—C14—N1—C185.4 (4)
C10—C11—C12—C131.5 (6)C15—C14—N1—C1385.0 (4)
C11—C12—C13—C80.8 (6)C24—C23—N2—C32152.8 (4)
C11—C12—C13—N1178.2 (4)C22—C23—N2—C3227.4 (5)
C9—C8—C13—C121.0 (5)C24—C23—N2—C3314.9 (5)
S1—C8—C13—C12173.1 (3)C22—C23—N2—C33164.9 (3)
C9—C8—C13—N1180.0 (3)C31—C32—N2—C23151.2 (4)
S1—C8—C13—N15.9 (5)C27—C32—N2—C2329.2 (5)
N1—C14—C15—C16173.9 (3)C31—C32—N2—C3316.4 (5)
C14—C15—C16—C17174.2 (4)C27—C32—N2—C33163.1 (3)
C15—C16—C17—C18178.5 (4)C34—C33—N2—C2383.5 (4)
C16—C17—C18—C19176.0 (6)C34—C33—N2—C3284.5 (4)
C25—C20—C21—C220.1 (6)C9—C8—S1—C6157.7 (3)
C26—C20—C21—C22178.0 (4)C13—C8—S1—C628.0 (3)
C20—C21—C22—C232.8 (6)C9—C8—S1—S228.0 (6)
C20—C21—C22—S2171.3 (3)C13—C8—S1—S2157.7 (3)
C21—C22—C23—N2176.6 (3)C5—C6—S1—C8159.1 (3)
S2—C22—C23—N29.3 (5)C1—C6—S1—C827.6 (4)
C21—C22—C23—C243.6 (5)C5—C6—S1—S27.2 (3)
S2—C22—C23—C24170.5 (3)C1—C6—S1—S2166.1 (3)
N2—C23—C24—C25178.3 (4)C28—C27—S2—C22152.0 (3)
C22—C23—C24—C251.9 (6)C32—C27—S2—C2233.1 (3)
C23—C24—C25—C200.7 (6)C28—C27—S2—S147.6 (5)
C21—C20—C25—C241.6 (6)C32—C27—S2—S1137.4 (3)
C26—C20—C25—C24179.8 (4)C21—C22—S2—C27151.1 (3)
C25—C20—C26—O2176.4 (4)C23—C22—S2—C2734.8 (3)
C21—C20—C26—O21.7 (7)C21—C22—S2—S10.9 (3)
C32—C27—C28—C292.5 (6)C23—C22—S2—S1173.2 (3)
S2—C27—C28—C29172.4 (4)C8—S1—S2—C2775.2 (5)
C27—C28—C29—C301.0 (7)C6—S1—S2—C2755.7 (3)
C28—C29—C30—C311.6 (8)C8—S1—S2—C2232.0 (4)
C29—C30—C31—C322.6 (7)C6—S1—S2—C22162.86 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C28—H28···O10.932.543.454 (5)168
C9—H9···O20.932.503.394 (5)162

Experimental details

Crystal data
Chemical formulaC19H21NOS
Mr311.43
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)8.4073 (9), 13.7719 (15), 14.6485 (15)
α, β, γ (°)93.957 (2), 98.781 (2), 90.983 (2)
V3)1671.5 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.20
Crystal size (mm)0.23 × 0.20 × 0.10
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1997)
Tmin, Tmax0.957, 0.981
No. of measured, independent and
observed [I > 2σ(I)] reflections
9878, 5800, 3575
Rint0.089
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.079, 0.210, 0.96
No. of reflections5800
No. of parameters399
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.35, 0.27

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000)', SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C28—H28···O10.932.543.454 (5)168
C9—H9···O20.932.503.394 (5)162
 

References

First citationBruker (2000). SMART and SAINT. Bruker AXS Inc.,Madison, Wisconsin, USA.
First citationHauck, M., Schönhaber, J., Zucchero, A. J., Hardcastle, K. I., Müller, T. J. J. & Bunz, U. H. F. (2007). J. Org. Chem. 72, 6714–6725.  Web of Science CSD CrossRef PubMed CAS
First citationKrishna, R. M., Kurshev, V. & Kervan, L. (1999). Phys. Chem. Chem. Phys. 11, 2833–2840.  Web of Science CrossRef
First citationSheldrick, G. M. (1997). SADABS. University of Göttingen, Germany.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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