supplementary materials


Acta Cryst. (2008). E64, o2458    [ doi:10.1107/S1600536808038890 ]

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

H. Wang, W. Xu, B. Zhang, W. Xiao and H. Wu

Abstract top

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

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)
graphiteRint = 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 = 0.26 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 reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.079H-atom parameters constrained
wR(F2) = 0.210Δρmax = 0.35 e Å3
S = 0.96Δρmin = 0.26 e Å3
5800 reflectionsAbsolute structure: ?
399 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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, °) 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, °) 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
Table 1
Hydrogen-bond geometry (Å, °)
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
References top

Bruker (2000). SMART, SAINT and SADABS. 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.

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.