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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): o2404.
Published online 2010 August 25. doi:  10.1107/S1600536810033751
PMCID: PMC3008074

(2E)-3-[4-(Dimethyl­amino)­phen­yl]-1-(2,5-dimethyl-3-thien­yl)prop-2-en-1-one

Abstract

The asymmetric unit of the title compound, C17H19NOS, contains two independent mol­ecules which differ in the dihedral angles between the five- and six-membered rings [12.52 (10) and 4.63 (11)°]. Weak inter­molecular C—H(...)O hydrogen bonds link the two independent mol­ecules into pseudocentrosymmetric dimers. In one mol­ecule, the O atom of the carbonyl group is disordered over two positions in a 0.699 (4):0.301 (4) ratio.

Related literature

For background and related crystal structures, see: Asiri et al. (2010a [triangle],b [triangle],c [triangle]). For graph-set notation, see: Bernstein et al. (1995 [triangle]).

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Object name is e-66-o2404-scheme1.jpg

Experimental

Crystal data

  • C17H19NOS
  • M r = 285.40
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2404-efi1.jpg
  • a = 7.7665 (2) Å
  • b = 12.8624 (4) Å
  • c = 16.0318 (4) Å
  • α = 79.917 (1)°
  • β = 80.029 (2)°
  • γ = 79.300 (1)°
  • V = 1532.90 (7) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.21 mm−1
  • T = 296 K
  • 0.32 × 0.23 × 0.20 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.947, T max = 0.962
  • 22632 measured reflections
  • 5536 independent reflections
  • 3543 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.156
  • S = 1.02
  • 5536 reflections
  • 373 parameters
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [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: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033751/cv2751sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033751/cv2751Isup2.hkl

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

Acknowledgments

The authors thank the Chemistry Department, King Abdul Aziz University, Jeddah, Saudi Arabia for providing research facilities and for the financial support of this work (grant No. 3–045/430).

supplementary crystallographic information

Comment

In continuation of our structural studies of 2,5-dimethylthiophen-3-yl derivatives (Asiri et al., 2010a, b, c), we present here the crystal structure of the title compound, (I) (Fig. 1).

The asymmetric unit of (I) contains two independent molecules having different configurations. In one molecule, the phenyl ring A (C1—C6) of 4-(dimethylamino)phenyl, the central group B (C9—C11/O1A) and group C (C12—C17/S1) of 2,5-dimethylthiophen are planar with r. m. s. deviation of 0.0070, 0.0455 and 0.0255 Å, respectively. The dimethylamino group D (C7/N1/C8) is of course planar. The dihedral angle between A/B, A/C, A/D and B/C is 16.29 (39), 12.52 (10), 4.53 (27) and 12.80 (40) (15)°, respectively. In the second molecule, the phenyl ring E (C18—C23) of 4-(dimethylamino)phenyl, the central group F (C26—C28/O2) and group G (C29—C34/S2) of 2,5-dimethylthiophen are planar with r. m. s. deviation of 0.0028, 0.0015 and 0.0317 Å, respectively. The dihedral angle between E/F, E/G and F/G is 8.01 (20), 4.63 (11), and 11.94 (18)°, respectively. The dimethylamino group H (C24/N2/C25) of this molecule is oriented at a dihedral angle of 2.88 (29) ° with its parent phenyl ring. The title compound essentially consists of dimers which are formed due to C—H···O type of intermolecular H-bonding (Table 1, Fig. 1) and complete R22(14) ring motif (Bernstein et al., 1995).

Experimental

A solution of 3-acetyl-2,5-dimethythiophene (0.38 g, 2.5 mmol) and N, N-dimethylbenzaldehyde (0.37 g, 2.5 mmol) in ethanolic solution of NaOH (3.0 g in 10 ml of methanol) was stirred for 16 h at room temperature. The solution was poured into ice cold water of pH = 2 (pH adjusted by HCl). The solid was separated and dissolved in CH2Cl2, washed with saturated solution of NaHCO3 and evaporated to dryness. The residual was recrystallized from methanol/chloroform to afford light yellow prisms of (I).

Yield: 86%; m.p. 375–376 K.

IR (KBr) \vmax cm-1: 2979 (C—Haliphatic), 1638 (Cδb=O), 1612 (CδbC), 1167 (C—N).

Refinement

In one independent molecule, the O-atom of carbonyl group is disordered over two set of sites with occupancy ratio of 0.699 (4):0.301 (4). The disordered O-atoms were refined anisotropically with constrained displacement ellipsoids.

The H-atoms were positioned geometrically (C–H = 0.93–0.96 Å) and refined as riding with Uiso(H) = xUeq(C), where x = 1.5 for methyl and x = 1.2 for aryl H-atoms.

Figures

Fig. 1.
Two independent molecules of (I) with the atomic numbering and 50% probability displacement ellipsoids. Dashed lines denote intermolecular hydrogen bonds. Only major part of the disordered atom (O1A) is shown.

Crystal data

C17H19NOSZ = 4
Mr = 285.40F(000) = 608
Triclinic, P1Dx = 1.237 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.7665 (2) ÅCell parameters from 3543 reflections
b = 12.8624 (4) Åθ = 1.6–25.3°
c = 16.0318 (4) ŵ = 0.21 mm1
α = 79.917 (1)°T = 296 K
β = 80.029 (2)°Prism, yellow
γ = 79.300 (1)°0.32 × 0.23 × 0.20 mm
V = 1532.90 (7) Å3

Data collection

Bruker Kappa APEXII CCD diffractometer5536 independent reflections
Radiation source: fine-focus sealed tube3543 reflections with I > 2σ(I)
graphiteRint = 0.039
Detector resolution: 8.10 pixels mm-1θmax = 25.3°, θmin = 1.6°
ω scansh = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −15→15
Tmin = 0.947, Tmax = 0.962l = −19→19
22632 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0809P)2 + 0.1945P] where P = (Fo2 + 2Fc2)/3
5536 reflections(Δ/σ)max < 0.001
373 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = −0.23 e Å3

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*/UeqOcc. (<1)
S20.67761 (9)0.59564 (5)0.72204 (4)0.0656 (2)
O20.4763 (3)0.71665 (15)0.46717 (12)0.0919 (7)
N20.8597 (3)0.3931 (2)0.04152 (14)0.0836 (7)
C180.6929 (3)0.54644 (19)0.25944 (15)0.0533 (6)
C190.6399 (3)0.5910 (2)0.18057 (15)0.0594 (6)
H190.56620.65690.17600.071*
C200.6922 (3)0.5417 (2)0.10983 (16)0.0634 (7)
H200.65270.57420.05850.076*
C210.8042 (3)0.4429 (2)0.11278 (15)0.0609 (6)
C220.8576 (3)0.3967 (2)0.19221 (16)0.0665 (7)
H220.93060.33060.19710.080*
C230.8036 (3)0.4480 (2)0.26256 (16)0.0628 (7)
H230.84220.41580.31410.075*
C240.9775 (4)0.2907 (3)0.0452 (2)0.0990 (10)
H24A0.91870.23710.08270.149*
H24B1.08280.29660.06660.149*
H24C1.00860.2709−0.01110.149*
C250.7976 (4)0.4364 (3)−0.03922 (18)0.0934 (10)
H25A0.84500.5008−0.06280.140*
H25B0.67060.4520−0.03040.140*
H25C0.83600.3851−0.07820.140*
C260.6300 (3)0.60139 (19)0.33348 (15)0.0569 (6)
H260.54750.66320.32480.068*
C270.6737 (3)0.57594 (19)0.41143 (15)0.0583 (6)
H270.76010.51690.42290.070*
C280.5897 (3)0.6381 (2)0.48031 (16)0.0600 (6)
C290.6421 (3)0.60325 (18)0.56638 (15)0.0523 (6)
C300.5930 (3)0.66231 (19)0.63207 (15)0.0551 (6)
C310.4827 (3)0.7713 (2)0.63494 (18)0.0718 (7)
H31A0.36090.76390.65410.108*
H31B0.49390.81240.57880.108*
H31C0.52310.80710.67380.108*
C320.7473 (3)0.50189 (19)0.59204 (15)0.0546 (6)
H320.79160.45180.55510.066*
C330.7761 (3)0.48573 (19)0.67384 (15)0.0569 (6)
C340.86743 (13)0.38708 (5)0.72324 (4)0.0717 (7)
H34A0.92080.33650.68510.108*
H34B0.78260.35600.76670.108*
H34C0.95730.40570.74950.108*
S10.33038 (9)0.95464 (5)−0.19233 (3)0.0728 (2)
O1A0.37293 (9)0.78720 (5)0.08108 (4)0.0854 (10)0.699 (4)
O1B0.44871 (9)0.80552 (5)0.06963 (3)0.0854 (10)0.301 (4)
N10.1145 (2)1.14648 (8)0.49058 (4)0.0711 (6)
C10.23647 (9)0.97971 (5)0.27862 (4)0.0537 (6)
C20.12944 (9)1.08011 (5)0.27559 (4)0.0605 (6)
H20.08581.11120.22500.073*
C30.0866 (3)1.1342 (2)0.34461 (15)0.0620 (6)
H30.01431.20060.34000.074*
C40.1505 (3)1.0908 (2)0.42243 (15)0.0565 (6)
C50.2551 (3)0.9896 (2)0.42629 (15)0.0598 (6)
H50.29800.95780.47700.072*
C60.2954 (3)0.9364 (2)0.35693 (15)0.0604 (6)
H60.36460.86890.36200.072*
C7−0.0074 (4)1.2468 (2)0.48868 (19)0.0850 (9)
H7A−0.12181.23520.48080.127*
H7B0.03591.29780.44220.127*
H7C−0.01701.27370.54180.127*
C80.1848 (4)1.1031 (3)0.56916 (17)0.0845 (9)
H8A0.31091.08300.55690.127*
H8B0.13251.04130.59600.127*
H8C0.15781.15600.60690.127*
C90.2893 (3)0.9220 (2)0.20630 (15)0.0630 (7)
H90.34810.85250.21820.076*
C100.2657 (3)0.9544 (2)0.12541 (15)0.0634 (7)
H100.20761.02340.11010.076*
C110.3278 (4)0.8854 (2)0.05931 (17)0.0710 (7)
C120.3116 (3)0.93130 (19)−0.03056 (15)0.0577 (6)
C130.3820 (3)0.8784 (2)−0.09877 (16)0.0618 (6)
C140.4959 (4)0.7703 (2)−0.1008 (2)0.0947 (10)
H14A0.42810.7207−0.11250.142*
H14B0.53610.7454−0.04630.142*
H14C0.59620.7758−0.14470.142*
C150.2189 (4)1.0352 (2)−0.05812 (16)0.0682 (7)
H150.16341.0824−0.02020.082*
C160.2183 (3)1.0591 (2)−0.14266 (15)0.0633 (7)
C170.1387 (4)1.1611 (2)−0.19338 (18)0.0881 (9)
H17A0.07531.2093−0.15490.132*
H17B0.05871.1454−0.22720.132*
H17C0.23121.1937−0.23040.132*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S20.0735 (4)0.0660 (5)0.0564 (4)−0.0018 (3)−0.0110 (3)−0.0153 (3)
O20.1119 (15)0.0755 (13)0.0746 (13)0.0380 (12)−0.0323 (11)−0.0120 (10)
N20.1085 (19)0.0809 (18)0.0615 (15)0.0004 (14)−0.0194 (13)−0.0201 (13)
C180.0545 (13)0.0483 (14)0.0575 (14)−0.0085 (11)−0.0171 (11)0.0000 (11)
C190.0623 (14)0.0565 (16)0.0566 (15)−0.0038 (12)−0.0178 (12)0.0018 (12)
C200.0667 (15)0.0723 (18)0.0515 (15)−0.0091 (13)−0.0226 (12)0.0017 (13)
C210.0693 (15)0.0609 (17)0.0547 (15)−0.0110 (13)−0.0162 (12)−0.0065 (13)
C220.0795 (17)0.0541 (16)0.0639 (16)0.0043 (13)−0.0222 (13)−0.0079 (13)
C230.0762 (16)0.0575 (16)0.0538 (15)−0.0021 (13)−0.0244 (12)−0.0003 (12)
C240.114 (3)0.091 (2)0.092 (2)0.001 (2)−0.0127 (19)−0.0354 (19)
C250.115 (2)0.111 (3)0.0604 (18)−0.020 (2)−0.0224 (17)−0.0192 (17)
C260.0607 (14)0.0495 (15)0.0594 (15)−0.0054 (11)−0.0147 (11)−0.0022 (12)
C270.0600 (14)0.0530 (15)0.0590 (15)0.0012 (12)−0.0146 (12)−0.0053 (12)
C280.0616 (14)0.0522 (15)0.0640 (16)−0.0001 (12)−0.0138 (12)−0.0073 (13)
C290.0525 (12)0.0469 (14)0.0553 (14)−0.0026 (11)−0.0091 (10)−0.0066 (11)
C300.0529 (13)0.0506 (15)0.0595 (15)−0.0050 (11)−0.0042 (11)−0.0099 (12)
C310.0766 (17)0.0560 (16)0.0794 (18)0.0037 (13)−0.0093 (14)−0.0180 (14)
C320.0576 (13)0.0484 (14)0.0547 (14)0.0027 (11)−0.0101 (11)−0.0090 (11)
C330.0580 (13)0.0548 (15)0.0550 (15)−0.0013 (11)−0.0107 (11)−0.0057 (12)
C340.0770 (17)0.0696 (18)0.0632 (16)0.0029 (14)−0.0205 (13)−0.0012 (14)
S10.0879 (5)0.0797 (5)0.0505 (4)−0.0107 (4)−0.0075 (3)−0.0141 (3)
O1A0.139 (3)0.0468 (13)0.0649 (14)0.0062 (15)−0.0284 (15)−0.0026 (11)
O1B0.139 (3)0.0468 (13)0.0649 (14)0.0062 (15)−0.0284 (15)−0.0026 (11)
N10.0802 (14)0.0799 (16)0.0510 (13)−0.0014 (12)−0.0086 (10)−0.0166 (12)
C10.0614 (14)0.0501 (14)0.0468 (13)−0.0070 (11)−0.0121 (11)0.0026 (11)
C20.0676 (15)0.0631 (17)0.0454 (14)0.0004 (12)−0.0156 (11)0.0024 (12)
C30.0669 (15)0.0568 (16)0.0552 (15)0.0049 (12)−0.0113 (12)−0.0026 (12)
C40.0552 (13)0.0636 (16)0.0480 (14)−0.0098 (12)−0.0060 (11)−0.0022 (12)
C50.0658 (15)0.0645 (17)0.0453 (14)−0.0044 (12)−0.0150 (11)0.0024 (12)
C60.0683 (15)0.0557 (16)0.0518 (15)0.0004 (12)−0.0131 (12)−0.0001 (12)
C70.0855 (19)0.085 (2)0.081 (2)0.0012 (16)−0.0016 (15)−0.0302 (17)
C80.095 (2)0.104 (2)0.0560 (17)−0.0147 (18)−0.0109 (15)−0.0182 (16)
C90.0800 (17)0.0522 (15)0.0543 (15)−0.0032 (13)−0.0164 (12)−0.0021 (12)
C100.0822 (17)0.0533 (16)0.0525 (15)−0.0024 (13)−0.0155 (12)−0.0055 (12)
C110.096 (2)0.0540 (17)0.0631 (17)−0.0001 (14)−0.0238 (14)−0.0093 (13)
C120.0728 (15)0.0477 (14)0.0536 (15)−0.0027 (12)−0.0170 (12)−0.0097 (12)
C130.0642 (14)0.0595 (16)0.0622 (16)−0.0053 (12)−0.0105 (12)−0.0138 (13)
C140.104 (2)0.083 (2)0.085 (2)0.0179 (18)−0.0061 (17)−0.0237 (17)
C150.0938 (19)0.0575 (17)0.0518 (15)0.0045 (14)−0.0202 (13)−0.0123 (12)
C160.0753 (16)0.0615 (17)0.0524 (15)−0.0063 (13)−0.0158 (12)−0.0046 (12)
C170.120 (2)0.076 (2)0.0632 (18)−0.0048 (18)−0.0308 (17)0.0076 (15)

Geometric parameters (Å, °)

S2—C301.713 (2)S1—C131.709 (3)
S2—C331.720 (2)O1A—C111.250 (3)
O2—C281.225 (3)O1B—C111.265 (3)
N2—C211.373 (3)N1—C41.371 (2)
N2—C251.443 (3)N1—C81.441 (3)
N2—C241.455 (3)N1—C71.451 (3)
C18—C231.391 (3)C1—C21.3980 (9)
C18—C191.391 (3)C1—C61.398 (2)
C18—C261.453 (3)C1—C91.444 (2)
C19—C201.361 (3)C2—C31.369 (3)
C19—H190.9300C2—H20.9300
C20—C211.399 (3)C3—C41.408 (3)
C20—H200.9300C3—H30.9300
C21—C221.404 (3)C4—C51.398 (3)
C22—C231.370 (3)C5—C61.367 (3)
C22—H220.9300C5—H50.9300
C23—H230.9300C6—H60.9300
C24—H24A0.9600C7—H7A0.9600
C24—H24B0.9600C7—H7B0.9600
C24—H24C0.9600C7—H7C0.9600
C25—H25A0.9600C8—H8A0.9600
C25—H25B0.9600C8—H8B0.9600
C25—H25C0.9600C8—H8C0.9600
C26—C271.321 (3)C9—C101.324 (3)
C26—H260.9300C9—H90.9300
C27—C281.466 (3)C10—C111.462 (3)
C27—H270.9300C10—H100.9300
C28—C291.477 (3)C11—C121.476 (3)
C29—C301.366 (3)C12—C131.369 (3)
C29—C321.439 (3)C12—C151.430 (3)
C30—C311.505 (3)C13—C141.505 (4)
C31—H31A0.9600C14—H14A0.9600
C31—H31B0.9600C14—H14B0.9600
C31—H31C0.9600C14—H14C0.9600
C32—C331.342 (3)C15—C161.337 (3)
C32—H320.9300C15—H150.9300
C33—C341.499 (2)C16—C171.505 (3)
C34—H34A0.9600C17—H17A0.9600
C34—H34B0.9600C17—H17B0.9600
C34—H34C0.9600C17—H17C0.9600
S1—C161.702 (3)
C30—S2—C3393.28 (11)C4—N1—C8121.07 (17)
C21—N2—C25122.0 (2)C4—N1—C7121.12 (16)
C21—N2—C24121.2 (2)C8—N1—C7117.61 (17)
C25—N2—C24116.7 (2)C2—C1—C6116.15 (11)
C23—C18—C19116.4 (2)C2—C1—C9123.76 (10)
C23—C18—C26123.4 (2)C6—C1—C9120.08 (15)
C19—C18—C26120.1 (2)C3—C2—C1122.24 (10)
C20—C19—C18122.4 (2)C3—C2—H2118.9
C20—C19—H19118.8C1—C2—H2118.9
C18—C19—H19118.8C2—C3—C4121.0 (2)
C19—C20—C21121.3 (2)C2—C3—H3119.5
C19—C20—H20119.4C4—C3—H3119.5
C21—C20—H20119.4N1—C4—C5121.7 (2)
N2—C21—C20121.7 (2)N1—C4—C3121.3 (2)
N2—C21—C22121.4 (2)C5—C4—C3117.0 (2)
C20—C21—C22116.9 (2)C6—C5—C4121.2 (2)
C23—C22—C21120.9 (2)C6—C5—H5119.4
C23—C22—H22119.6C4—C5—H5119.4
C21—C22—H22119.6C5—C6—C1122.4 (2)
C22—C23—C18122.2 (2)C5—C6—H6118.8
C22—C23—H23118.9C1—C6—H6118.8
C18—C23—H23118.9N1—C7—H7A109.5
N2—C24—H24A109.5N1—C7—H7B109.5
N2—C24—H24B109.5H7A—C7—H7B109.5
H24A—C24—H24B109.5N1—C7—H7C109.5
N2—C24—H24C109.5H7A—C7—H7C109.5
H24A—C24—H24C109.5H7B—C7—H7C109.5
H24B—C24—H24C109.5N1—C8—H8A109.5
N2—C25—H25A109.5N1—C8—H8B109.5
N2—C25—H25B109.5H8A—C8—H8B109.5
H25A—C25—H25B109.5N1—C8—H8C109.5
N2—C25—H25C109.5H8A—C8—H8C109.5
H25A—C25—H25C109.5H8B—C8—H8C109.5
H25B—C25—H25C109.5C10—C9—C1129.1 (2)
C27—C26—C18129.1 (2)C10—C9—H9115.5
C27—C26—H26115.4C1—C9—H9115.5
C18—C26—H26115.4C9—C10—C11122.3 (2)
C26—C27—C28121.9 (2)C9—C10—H10118.9
C26—C27—H27119.1C11—C10—H10118.9
C28—C27—H27119.1O1A—C11—C10119.3 (2)
O2—C28—C27120.7 (2)O1B—C11—C10120.9 (2)
O2—C28—C29120.5 (2)O1A—C11—C12121.6 (2)
C27—C28—C29118.8 (2)O1B—C11—C12115.3 (2)
C30—C29—C32111.6 (2)C10—C11—C12118.6 (2)
C30—C29—C28124.1 (2)C13—C12—C15111.0 (2)
C32—C29—C28124.2 (2)C13—C12—C11123.9 (2)
C29—C30—C31130.2 (2)C15—C12—C11125.1 (2)
C29—C30—S2110.76 (17)C12—C13—C14129.6 (2)
C31—C30—S2119.09 (18)C12—C13—S1110.73 (18)
C30—C31—H31A109.5C14—C13—S1119.7 (2)
C30—C31—H31B109.5C13—C14—H14A109.5
H31A—C31—H31B109.5C13—C14—H14B109.5
C30—C31—H31C109.5H14A—C14—H14B109.5
H31A—C31—H31C109.5C13—C14—H14C109.5
H31B—C31—H31C109.5H14A—C14—H14C109.5
C33—C32—C29114.3 (2)H14B—C14—H14C109.5
C33—C32—H32122.8C16—C15—C12114.7 (2)
C29—C32—H32122.8C16—C15—H15122.7
C32—C33—C34128.5 (2)C12—C15—H15122.7
C32—C33—S2109.98 (18)C15—C16—C17128.8 (2)
C34—C33—S2121.41 (15)C15—C16—S1110.20 (19)
C33—C34—H34A109.5C17—C16—S1120.93 (19)
C33—C34—H34B109.5C16—C17—H17A109.5
H34A—C34—H34B109.5C16—C17—H17B109.5
C33—C34—H34C109.5H17A—C17—H17B109.5
H34A—C34—H34C109.5C16—C17—H17C109.5
H34B—C34—H34C109.5H17A—C17—H17C109.5
C16—S1—C1393.33 (12)H17B—C17—H17C109.5
C23—C18—C19—C200.2 (4)C1—C2—C3—C40.5 (3)
C26—C18—C19—C20−178.6 (2)C8—N1—C4—C50.5 (4)
C18—C19—C20—C21−0.5 (4)C7—N1—C4—C5−174.2 (2)
C25—N2—C21—C20−3.8 (4)C8—N1—C4—C3−178.1 (2)
C24—N2—C21—C20179.5 (3)C7—N1—C4—C37.2 (4)
C25—N2—C21—C22176.3 (3)C2—C3—C4—N1177.12 (19)
C24—N2—C21—C22−0.5 (4)C2—C3—C4—C5−1.5 (3)
C19—C20—C21—N2−179.1 (2)N1—C4—C5—C6−177.6 (2)
C19—C20—C21—C220.9 (4)C3—C4—C5—C61.1 (4)
N2—C21—C22—C23179.0 (2)C4—C5—C6—C10.5 (4)
C20—C21—C22—C23−1.0 (4)C2—C1—C6—C5−1.5 (3)
C21—C22—C23—C180.7 (4)C9—C1—C6—C5177.3 (2)
C19—C18—C23—C22−0.3 (4)C2—C1—C9—C107.7 (3)
C26—C18—C23—C22178.4 (2)C6—C1—C9—C10−171.1 (3)
C23—C18—C26—C276.1 (4)C1—C9—C10—C11−180.0 (2)
C19—C18—C26—C27−175.2 (2)C9—C10—C11—O1A14.4 (4)
C18—C26—C27—C28−176.8 (2)C9—C10—C11—O1B−20.8 (4)
C26—C27—C28—O2−0.5 (4)C9—C10—C11—C12−174.1 (2)
C26—C27—C28—C29178.5 (2)O1A—C11—C12—C13−16.1 (4)
O2—C28—C29—C30−10.8 (4)O1B—C11—C12—C1317.9 (4)
C27—C28—C29—C30170.2 (2)C10—C11—C12—C13172.6 (2)
O2—C28—C29—C32167.6 (2)O1A—C11—C12—C15162.9 (2)
C27—C28—C29—C32−11.4 (4)O1B—C11—C12—C15−163.2 (2)
C32—C29—C30—C31−179.4 (2)C10—C11—C12—C15−8.4 (4)
C28—C29—C30—C31−0.8 (4)C15—C12—C13—C14176.9 (3)
C32—C29—C30—S21.0 (3)C11—C12—C13—C14−4.0 (4)
C28—C29—C30—S2179.60 (19)C15—C12—C13—S1−1.1 (3)
C33—S2—C30—C29−1.35 (19)C11—C12—C13—S1178.0 (2)
C33—S2—C30—C31179.03 (19)C16—S1—C13—C121.2 (2)
C30—C29—C32—C33−0.1 (3)C16—S1—C13—C14−177.1 (2)
C28—C29—C32—C33−178.6 (2)C13—C12—C15—C160.5 (3)
C29—C32—C33—C34175.0 (2)C11—C12—C15—C16−178.6 (3)
C29—C32—C33—S2−0.9 (3)C12—C15—C16—C17−178.2 (3)
C30—S2—C33—C321.29 (19)C12—C15—C16—S10.4 (3)
C30—S2—C33—C34−174.97 (18)C13—S1—C16—C15−0.9 (2)
C6—C1—C2—C31.04 (17)C13—S1—C16—C17177.8 (2)
C9—C1—C2—C3−177.80 (18)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C6—H6···O20.932.483.275 (3)143
C19—H19···O1A0.932.523.317 (9)144
C19—H19···O1B0.932.483.264 (3)142

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2751).

References

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