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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1831.
Published online 2009 July 11. doi:  10.1107/S1600536809026403
PMCID: PMC2977171

4,4′,4′′-Tris(2-pyrid­yl)-2,2′,2′′-[(2,4,6-trimethyl­benzene-1,3,5-tri­yl)tris­(methyl­ene)tris­(sulfanedi­yl)]tripyrimidine

Abstract

The title compound, C39H33N9S3, features a mesitylene unit substituted with three thio­ether arms. The distances from the center of mesitylene unit to the N atoms of the three pyridine rings in the arms are 10.05 (1), 9.94 (3) and 8.79 (3) Å. The crystal structure shows weak intra­molecular C—H(...)N hydrogen bonds.

Related literature

For the potential use of tripodal ligands in the construction of organic-inorganic architectures, see: Hammes et al. (1998 [triangle]); Hiraoka et al. (2005 [triangle]). For the use of flexible thio­ether ligands to produce extended structures with metal ions, see: Dong et al. (2008a [triangle],b [triangle]); Zhang et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1831-scheme1.jpg

Experimental

Crystal data

  • C39H33N9S3
  • M r = 723.92
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1831-efi1.jpg
  • a = 11.966 (2) Å
  • b = 10.520 (2) Å
  • c = 31.959 (6) Å
  • β = 108.369 (6)°
  • V = 3818.1 (12) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.24 mm−1
  • T = 293 K
  • 0.25 × 0.20 × 0.18 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2000 [triangle]) T min = 0.944, T max = 0.959
  • 17715 measured reflections
  • 6544 independent reflections
  • 2957 reflections with I > 2σ(I)
  • R int = 0.107

Refinement

  • R[F 2 > 2σ(F 2)] = 0.081
  • wR(F 2) = 0.163
  • S = 1.08
  • 6544 reflections
  • 460 parameters
  • H-atom parameters constrained
  • Δρmax = 0.89 e Å−3
  • Δρmin = −0.26 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 I, global. DOI: 10.1107/S1600536809026403/bt2991sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026403/bt2991Isup2.hkl

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

Acknowledgments

The authors thank the Program for Young Excellent Talents in Southeast University for financial support.

supplementary crystallographic information

Comment

Recent years have witnessed an explosion of great interest in tripodal ligands for their potential applications to construct intriguing hybrid organic-inorganic architectures and topologies (Hammes et al. 1998; Hiraoka et al., 2005). On the other hand, flexible thioether ligands have been successfully used to produce various extended structures with metal ions (Dong et al., 2008a,b; Zhang et al., 2008). Herein, we report the crystal structure of 2,2',2''-(2,4,6-trimethylbenzene-1,3,5-triyl) tris(methylene)tris(sulfanediyl)tris(4-(pyridin-2-yl)pyrimidine).

The tripodal character of C33H30N10S3 arises from the three thioether arms surrounding a central mesitylene. The distances of the center of mesitylene to the nitrogen atoms of three pyridine rings in the arms are 10.05 (1), 9.94 (3) and 8.79 (3) °, respectively. The crystal structure shows wear intramolecular weak C—H···N hydrogen bonds.

Experimental

An 95% ethanol solution (50 ml) of 1,3,5-tris(chloromethyl)-2,4,6-trimethylbenzene (2.64 g, 10 mmol) was added to a dry ethanol solution (300 ml) containing 4-(pyridin-2-yl)pyrimidine-2-thiol (5.67 g, 30 mmol) and sodium hydroxide (1.20 g, 30 mmol). The solution was stirred and refluxed for 8 h. Yellow precipitates were filtered out, washed by water and ethanol, and dried in vacuum. Yield (4.42 g) 61.0%. The yellow crystals were obtained after the filter slowly evaporated.

Refinement

All the H atoms were located in a difference map and refined using a riding model with C-H ranging from 0.93Å to 0.97Å and Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(Cmethyl). There are holes in the structure but the largest residual peak value is 0.892e/Å3, and no model for any solvent could be found.

Figures

Fig. 1.
Structure of the title compound with 15% displacement ellipsoids.
Fig. 2.
The three-dimensional supramolecular network of the title compound.

Crystal data

C39H33N9S3F(000) = 1512
Mr = 723.92Dx = 1.259 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 780 reflections
a = 11.966 (2) Åθ = 2.4–28.0°
b = 10.520 (2) ŵ = 0.24 mm1
c = 31.959 (6) ÅT = 293 K
β = 108.369 (6)°Block, yellow
V = 3818.1 (12) Å30.25 × 0.20 × 0.18 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer6544 independent reflections
Radiation source: fine-focus sealed tube2957 reflections with I > 2σ(I)
graphiteRint = 0.107
[var phi] and ω scansθmax = 25.1°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)h = −12→14
Tmin = 0.944, Tmax = 0.959k = −12→11
17715 measured reflectionsl = −38→38

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)] = 0.081Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.01P)2 + 1.28P] where P = (Fo2 + 2Fc2)/3
6544 reflections(Δ/σ)max < 0.001
460 parametersΔρmax = 0.89 e Å3
0 restraintsΔρmin = −0.26 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*/Ueq
S10.58642 (11)−0.78603 (12)−0.22867 (4)0.0754 (4)
S20.62715 (13)−1.06746 (13)−0.05185 (4)0.0883 (5)
S30.23200 (12)−0.66957 (13)−0.12895 (5)0.0924 (5)
C10.4361 (4)−0.9300 (4)−0.20145 (14)0.0620 (12)
C20.3434 (4)−0.8618 (5)−0.19733 (16)0.0680 (13)
C30.3010 (4)−0.8814 (5)−0.16132 (17)0.0679 (13)
C40.3590 (5)−0.9676 (5)−0.12875 (16)0.0705 (13)
C50.4568 (5)−1.0361 (4)−0.13279 (16)0.0674 (13)
C60.4962 (4)−1.0149 (4)−0.16834 (16)0.0626 (12)
C70.2812 (5)−0.7628 (5)−0.23179 (17)0.0993 (17)
H7A0.3176−0.7599−0.25460.149*
H7B0.2871−0.6809−0.21800.149*
H7C0.1997−0.7855−0.24440.149*
C80.3170 (5)−0.9901 (5)−0.08946 (17)0.1026 (18)
H8A0.2498−0.9373−0.09190.154*
H8B0.3789−0.9693−0.06290.154*
H8C0.2956−1.0778−0.08870.154*
C90.6043 (4)−1.0849 (5)−0.17075 (16)0.0833 (15)
H9A0.6216−1.0599−0.19690.125*
H9B0.5900−1.1748−0.17150.125*
H9C0.6699−1.0645−0.14530.125*
C100.4793 (4)−0.9128 (5)−0.24122 (14)0.0740 (14)
H10A0.4139−0.8914−0.26710.089*
H10B0.5149−0.9908−0.24710.089*
C110.6446 (4)−0.7921 (4)−0.27308 (14)0.0616 (12)
C120.6554 (5)−0.8711 (5)−0.33626 (15)0.0713 (13)
H12A0.6288−0.9253−0.36040.086*
C130.7498 (4)−0.7944 (5)−0.33389 (14)0.0645 (12)
H13A0.7859−0.7955−0.35580.077*
C140.7884 (4)−0.7169 (4)−0.29843 (14)0.0532 (11)
C150.8931 (4)−0.6337 (4)−0.29058 (15)0.0626 (12)
C160.9256 (5)−0.5489 (5)−0.25625 (15)0.0745 (14)
H16A0.8817−0.5408−0.23700.089*
C171.0242 (5)−0.4764 (5)−0.2511 (2)0.0908 (17)
H17A1.0490−0.4194−0.22770.109*
C181.0852 (5)−0.4882 (6)−0.2800 (2)0.0940 (17)
H18A1.1508−0.4379−0.27770.113*
C191.0482 (6)−0.5740 (6)−0.3118 (2)0.1053 (19)
H19A1.0927−0.5843−0.33080.126*
C200.5140 (5)−1.1352 (4)−0.09856 (16)0.0861 (16)
H20A0.5488−1.2005−0.11200.103*
H20B0.4543−1.1750−0.08830.103*
C210.7111 (4)−1.2020 (5)−0.03108 (15)0.0686 (13)
C220.8719 (6)−1.2798 (7)0.02049 (17)0.0975 (19)
H22A0.9365−1.26900.04560.117*
C230.8548 (5)−1.3965 (6)0.00115 (17)0.0937 (17)
H23A0.9057−1.46400.01230.112*
C240.7563 (5)−1.4094 (5)−0.03647 (16)0.0699 (13)
C250.7259 (5)−1.5296 (5)−0.06142 (17)0.0773 (14)
C260.6307 (5)−1.5380 (6)−0.09824 (19)0.0870 (16)
H26A0.5843−1.4669−0.10870.104*
C270.6038 (6)−1.6508 (8)−0.1196 (2)0.108 (2)
H27A0.5392−1.6576−0.14490.129*
C280.6720 (9)−1.7529 (7)−0.1036 (2)0.120 (2)
H28A0.6549−1.8316−0.11750.144*
C290.7660 (9)−1.7382 (7)−0.0670 (3)0.140 (3)
H29A0.8116−1.8098−0.05620.168*
C300.1921 (5)−0.8156 (5)−0.15912 (17)0.0876 (15)
H30A0.1501−0.8700−0.14460.105*
H30B0.1406−0.7979−0.18870.105*
C310.0955 (5)−0.6028 (6)−0.13059 (16)0.0783 (15)
C32−0.0991 (6)−0.6111 (7)−0.15071 (19)0.105 (2)
H32A−0.1702−0.6522−0.16430.126*
C33−0.1041 (5)−0.4911 (7)−0.13345 (17)0.0944 (18)
H33A−0.1750−0.4513−0.13560.113*
C340.0034 (5)−0.4348 (6)−0.11291 (15)0.0763 (15)
C350.0108 (5)−0.3091 (5)−0.09093 (16)0.0720 (13)
C360.1165 (5)−0.2639 (6)−0.06459 (16)0.0807 (15)
H36A0.1845−0.3123−0.05980.097*
C370.1220 (6)−0.1456 (7)−0.04502 (18)0.0881 (16)
H37A0.1930−0.1120−0.02730.106*
C380.0216 (8)−0.0821 (6)−0.0527 (2)0.1056 (19)
H38A0.0216−0.0022−0.04030.127*
C39−0.0823 (7)−0.1338 (7)−0.0790 (2)0.1069 (19)
H39A−0.1514−0.0877−0.08340.128*
N10.7367 (3)−0.7132 (3)−0.26700 (11)0.0583 (9)
N20.5992 (3)−0.8731 (3)−0.30604 (13)0.0677 (10)
N30.9526 (4)−0.6468 (4)−0.31899 (14)0.0890 (13)
N40.8019 (4)−1.1798 (4)0.00566 (14)0.0881 (13)
N50.6858 (3)−1.3116 (4)−0.05227 (11)0.0648 (10)
N60.7987 (5)−1.6291 (5)−0.04492 (15)0.1137 (17)
N70.1042 (4)−0.4918 (4)−0.11146 (12)0.0690 (11)
N8−0.0016 (4)−0.6716 (4)−0.14938 (13)0.0852 (13)
N9−0.0891 (4)−0.2464 (5)−0.09860 (15)0.0893 (13)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0783 (9)0.0869 (10)0.0638 (8)−0.0206 (7)0.0263 (7)−0.0125 (7)
S20.0980 (10)0.0786 (10)0.0728 (9)−0.0051 (8)0.0046 (7)−0.0037 (7)
S30.0623 (9)0.0896 (11)0.1195 (12)−0.0098 (8)0.0202 (8)−0.0139 (9)
C10.053 (3)0.069 (3)0.060 (3)−0.010 (3)0.012 (3)−0.002 (3)
C20.052 (3)0.071 (3)0.069 (3)−0.015 (3)0.002 (3)0.005 (3)
C30.052 (3)0.072 (3)0.077 (3)−0.010 (3)0.017 (3)0.004 (3)
C40.069 (3)0.079 (4)0.066 (3)−0.019 (3)0.025 (3)0.001 (3)
C50.067 (3)0.061 (3)0.060 (3)−0.011 (3)−0.001 (3)−0.001 (2)
C60.058 (3)0.067 (3)0.055 (3)−0.013 (3)0.007 (3)−0.006 (3)
C70.096 (4)0.097 (4)0.097 (4)0.001 (3)0.019 (3)0.030 (3)
C80.105 (4)0.119 (5)0.096 (4)−0.006 (4)0.048 (4)0.022 (3)
C90.070 (3)0.096 (4)0.079 (3)0.002 (3)0.018 (3)−0.009 (3)
C100.074 (3)0.084 (4)0.060 (3)−0.018 (3)0.015 (3)−0.005 (3)
C110.061 (3)0.062 (3)0.054 (3)0.008 (3)0.008 (2)0.008 (2)
C120.072 (4)0.084 (4)0.056 (3)0.004 (3)0.017 (3)−0.016 (3)
C130.054 (3)0.085 (4)0.051 (3)0.002 (3)0.011 (2)−0.005 (3)
C140.050 (3)0.058 (3)0.048 (3)0.008 (2)0.011 (2)0.002 (2)
C150.056 (3)0.070 (3)0.057 (3)0.004 (3)0.009 (3)0.006 (3)
C160.071 (4)0.089 (4)0.059 (3)−0.011 (3)0.014 (3)−0.008 (3)
C170.080 (4)0.092 (4)0.087 (4)−0.021 (3)0.008 (4)−0.013 (3)
C180.066 (4)0.106 (5)0.101 (5)−0.018 (3)0.012 (4)−0.010 (4)
C190.085 (5)0.132 (5)0.110 (5)−0.024 (4)0.046 (4)−0.010 (4)
C200.088 (4)0.072 (3)0.076 (3)−0.017 (3)−0.007 (3)0.003 (3)
C210.066 (3)0.080 (4)0.054 (3)−0.015 (3)0.011 (3)−0.001 (3)
C220.109 (5)0.090 (5)0.060 (3)−0.007 (4)−0.020 (3)−0.003 (4)
C230.105 (5)0.096 (5)0.066 (4)0.005 (4)0.007 (3)0.012 (3)
C240.080 (4)0.073 (4)0.054 (3)−0.006 (3)0.016 (3)0.010 (3)
C250.081 (4)0.083 (4)0.063 (3)−0.006 (3)0.016 (3)0.004 (3)
C260.072 (4)0.096 (5)0.088 (4)0.000 (3)0.018 (3)−0.024 (3)
C270.093 (5)0.115 (6)0.111 (5)−0.007 (5)0.027 (4)−0.029 (5)
C280.169 (7)0.094 (6)0.091 (5)−0.047 (5)0.031 (5)−0.023 (4)
C290.222 (9)0.072 (5)0.104 (5)0.009 (5)0.021 (6)0.000 (4)
C300.080 (4)0.078 (4)0.103 (4)−0.013 (3)0.026 (3)−0.010 (3)
C310.080 (4)0.087 (4)0.059 (3)−0.010 (3)0.009 (3)0.014 (3)
C320.057 (4)0.162 (7)0.086 (4)−0.028 (4)0.009 (3)−0.022 (4)
C330.067 (4)0.146 (6)0.078 (4)−0.009 (4)0.034 (3)−0.021 (4)
C340.063 (4)0.104 (5)0.056 (3)−0.015 (4)0.011 (3)0.014 (3)
C350.068 (4)0.090 (4)0.066 (3)0.004 (3)0.032 (3)0.007 (3)
C360.069 (4)0.107 (5)0.068 (3)−0.007 (3)0.024 (3)0.003 (3)
C370.079 (4)0.103 (5)0.090 (4)−0.006 (4)0.039 (3)−0.008 (4)
C380.130 (6)0.111 (5)0.089 (4)−0.001 (5)0.053 (5)−0.006 (4)
C390.093 (5)0.121 (6)0.119 (5)0.009 (4)0.050 (4)−0.010 (5)
N10.052 (2)0.058 (2)0.060 (2)−0.004 (2)0.0120 (19)−0.0016 (19)
N20.066 (3)0.068 (3)0.060 (2)−0.004 (2)0.007 (2)−0.014 (2)
N30.070 (3)0.115 (4)0.093 (3)−0.023 (3)0.042 (3)−0.023 (3)
N40.104 (4)0.083 (3)0.067 (3)−0.014 (3)0.013 (3)−0.007 (2)
N50.065 (3)0.074 (3)0.052 (2)−0.013 (2)0.0129 (19)0.002 (2)
N60.162 (5)0.076 (3)0.079 (3)0.017 (4)0.003 (3)0.007 (3)
N70.055 (3)0.080 (3)0.073 (3)−0.004 (2)0.021 (2)0.003 (2)
N80.059 (3)0.119 (4)0.080 (3)−0.023 (3)0.024 (2)−0.009 (3)
N90.074 (3)0.108 (4)0.093 (3)0.005 (3)0.036 (3)−0.003 (3)

Geometric parameters (Å, °)

S1—C111.768 (5)C18—H18A0.9300
S1—C101.805 (5)C19—N31.336 (7)
S2—C211.741 (5)C19—H19A0.9300
S2—C201.815 (4)C20—H20A0.9700
S3—C311.763 (6)C20—H20B0.9700
S3—C301.796 (5)C21—N51.323 (5)
C1—C21.361 (6)C21—N41.345 (6)
C1—C61.398 (6)C22—N41.335 (6)
C1—C101.527 (6)C22—C231.361 (6)
C2—C31.412 (6)C22—H22A0.9300
C2—C71.528 (6)C23—C241.400 (7)
C3—C41.390 (6)C23—H23A0.9300
C3—C301.497 (7)C24—N51.324 (6)
C4—C51.415 (7)C24—C251.478 (7)
C4—C81.511 (7)C25—N61.357 (6)
C5—C61.379 (7)C25—C261.358 (7)
C5—C201.510 (6)C26—C271.355 (7)
C6—C91.511 (7)C26—H26A0.9300
C7—H7A0.9600C27—C281.349 (8)
C7—H7B0.9600C27—H27A0.9300
C7—H7C0.9600C28—C291.352 (9)
C8—H8A0.9600C28—H28A0.9300
C8—H8B0.9600C29—N61.340 (7)
C8—H8C0.9600C29—H29A0.9300
C9—H9A0.9600C30—H30A0.9700
C9—H9B0.9600C30—H30B0.9700
C9—H9C0.9600C31—N71.307 (6)
C10—H10A0.9700C31—N81.339 (6)
C10—H10B0.9700C32—N81.319 (7)
C11—N21.330 (5)C32—C331.386 (7)
C11—N11.344 (5)C32—H32A0.9300
C12—N21.340 (6)C33—C341.380 (7)
C12—C131.371 (6)C33—H33A0.9300
C12—H12A0.9300C34—N71.334 (6)
C13—C141.353 (5)C34—C351.487 (7)
C13—H13A0.9300C35—N91.319 (6)
C14—N11.336 (5)C35—C361.365 (7)
C14—C151.484 (6)C36—C371.386 (7)
C15—N31.325 (6)C36—H36A0.9300
C15—C161.371 (6)C37—C381.328 (8)
C16—C171.370 (7)C37—H37A0.9300
C16—H16A0.9300C38—C391.375 (8)
C17—C181.352 (8)C38—H38A0.9300
C17—H17A0.9300C39—N91.329 (7)
C18—C191.328 (7)C39—H39A0.9300
C11—S1—C10103.1 (2)S2—C20—H20A109.2
C21—S2—C20100.7 (2)C5—C20—H20B109.2
C31—S3—C30103.7 (3)S2—C20—H20B109.2
C2—C1—C6120.3 (4)H20A—C20—H20B107.9
C2—C1—C10121.2 (4)N5—C21—N4126.1 (5)
C6—C1—C10118.5 (5)N5—C21—S2120.1 (4)
C1—C2—C3121.0 (4)N4—C21—S2113.7 (4)
C1—C2—C7121.1 (5)N4—C22—C23124.2 (5)
C3—C2—C7117.9 (5)N4—C22—H22A117.9
C4—C3—C2118.9 (5)C23—C22—H22A117.9
C4—C3—C30120.2 (5)C22—C23—C24116.3 (5)
C2—C3—C30120.8 (5)C22—C23—H23A121.9
C3—C4—C5119.7 (4)C24—C23—H23A121.9
C3—C4—C8120.4 (5)N5—C24—C23121.0 (5)
C5—C4—C8119.9 (5)N5—C24—C25116.1 (5)
C6—C5—C4120.0 (4)C23—C24—C25122.9 (5)
C6—C5—C20120.9 (5)N6—C25—C26123.1 (5)
C4—C5—C20119.0 (5)N6—C25—C24115.6 (5)
C5—C6—C1119.9 (5)C26—C25—C24121.3 (5)
C5—C6—C9118.9 (4)C27—C26—C25119.7 (6)
C1—C6—C9121.2 (4)C27—C26—H26A120.2
C2—C7—H7A109.5C25—C26—H26A120.2
C2—C7—H7B109.5C28—C27—C26119.2 (6)
H7A—C7—H7B109.5C28—C27—H27A120.4
C2—C7—H7C109.5C26—C27—H27A120.4
H7A—C7—H7C109.5C27—C28—C29118.3 (7)
H7B—C7—H7C109.5C27—C28—H28A120.8
C4—C8—H8A109.5C29—C28—H28A120.8
C4—C8—H8B109.5N6—C29—C28125.4 (7)
H8A—C8—H8B109.5N6—C29—H29A117.3
C4—C8—H8C109.5C28—C29—H29A117.3
H8A—C8—H8C109.5C3—C30—S3109.4 (3)
H8B—C8—H8C109.5C3—C30—H30A109.8
C6—C9—H9A109.5S3—C30—H30A109.8
C6—C9—H9B109.5C3—C30—H30B109.8
H9A—C9—H9B109.5S3—C30—H30B109.8
C6—C9—H9C109.5H30A—C30—H30B108.2
H9A—C9—H9C109.5N7—C31—N8128.5 (5)
H9B—C9—H9C109.5N7—C31—S3113.9 (4)
C1—C10—S1107.8 (3)N8—C31—S3117.5 (5)
C1—C10—H10A110.1N8—C32—C33125.1 (5)
S1—C10—H10A110.1N8—C32—H32A117.4
C1—C10—H10B110.1C33—C32—H32A117.4
S1—C10—H10B110.1C34—C33—C32115.4 (6)
H10A—C10—H10B108.5C34—C33—H33A122.3
N2—C11—N1128.4 (4)C32—C33—H33A122.3
N2—C11—S1119.6 (4)N7—C34—C33121.3 (6)
N1—C11—S1111.9 (3)N7—C34—C35117.7 (5)
N2—C12—C13124.1 (4)C33—C34—C35120.9 (6)
N2—C12—H12A117.9N9—C35—C36123.3 (5)
C13—C12—H12A117.9N9—C35—C34116.2 (5)
C14—C13—C12117.3 (4)C36—C35—C34120.4 (6)
C14—C13—H13A121.4C35—C36—C37119.6 (6)
C12—C13—H13A121.4C35—C36—H36A120.2
N1—C14—C13122.1 (4)C37—C36—H36A120.2
N1—C14—C15115.0 (4)C38—C37—C36117.2 (6)
C13—C14—C15122.9 (4)C38—C37—H37A121.4
N3—C15—C16122.6 (5)C36—C37—H37A121.4
N3—C15—C14115.4 (4)C37—C38—C39120.4 (6)
C16—C15—C14122.0 (5)C37—C38—H38A119.8
C17—C16—C15118.3 (5)C39—C38—H38A119.8
C17—C16—H16A120.9N9—C39—C38123.3 (6)
C15—C16—H16A120.9N9—C39—H39A118.3
C18—C17—C16119.8 (5)C38—C39—H39A118.4
C18—C17—H17A120.1C14—N1—C11115.2 (4)
C16—C17—H17A120.1C11—N2—C12112.9 (4)
C19—C18—C17117.7 (6)C15—N3—C19116.0 (5)
C19—C18—H18A121.1C22—N4—C21114.6 (4)
C17—C18—H18A121.1C21—N5—C24117.8 (4)
C18—C19—N3125.5 (6)C29—N6—C25114.2 (5)
C18—C19—H19A117.2C31—N7—C34116.6 (5)
N3—C19—H19A117.2C32—N8—C31112.8 (5)
C5—C20—S2112.0 (3)C35—N9—C39116.2 (5)
C5—C20—H20A109.2
C6—C1—C2—C3−4.4 (7)N6—C25—C26—C271.4 (8)
C10—C1—C2—C3177.6 (4)C24—C25—C26—C27−178.2 (5)
C6—C1—C2—C7176.3 (4)C25—C26—C27—C280.4 (9)
C10—C1—C2—C7−1.6 (6)C26—C27—C28—C29−0.8 (10)
C1—C2—C3—C43.1 (7)C27—C28—C29—N6−0.7 (12)
C7—C2—C3—C4−177.7 (4)C4—C3—C30—S390.2 (5)
C1—C2—C3—C30−174.0 (4)C2—C3—C30—S3−92.7 (5)
C7—C2—C3—C305.2 (6)C31—S3—C30—C3178.6 (4)
C2—C3—C4—C5−1.6 (6)C30—S3—C31—N7−177.8 (4)
C30—C3—C4—C5175.5 (4)C30—S3—C31—N84.4 (4)
C2—C3—C4—C8179.3 (4)N8—C32—C33—C34−1.1 (8)
C30—C3—C4—C8−3.6 (7)C32—C33—C34—N72.2 (7)
C3—C4—C5—C61.6 (7)C32—C33—C34—C35−176.8 (4)
C8—C4—C5—C6−179.3 (4)N7—C34—C35—N9169.9 (4)
C3—C4—C5—C20−176.2 (4)C33—C34—C35—N9−11.1 (7)
C8—C4—C5—C202.9 (6)N7—C34—C35—C36−9.9 (6)
C4—C5—C6—C1−2.9 (6)C33—C34—C35—C36169.1 (5)
C20—C5—C6—C1174.9 (4)N9—C35—C36—C37−1.0 (7)
C4—C5—C6—C9177.2 (4)C34—C35—C36—C37178.8 (4)
C20—C5—C6—C9−4.9 (6)C35—C36—C37—C380.9 (7)
C2—C1—C6—C54.4 (6)C36—C37—C38—C390.1 (8)
C10—C1—C6—C5−177.6 (4)C37—C38—C39—N9−1.2 (9)
C2—C1—C6—C9−175.8 (4)C13—C14—N1—C110.3 (6)
C10—C1—C6—C92.2 (6)C15—C14—N1—C11−177.5 (3)
C2—C1—C10—S188.1 (5)N2—C11—N1—C140.3 (6)
C6—C1—C10—S1−89.9 (4)S1—C11—N1—C14177.2 (3)
C11—S1—C10—C1171.6 (3)N1—C11—N2—C12−0.5 (6)
C10—S1—C11—N24.4 (4)S1—C11—N2—C12−177.2 (3)
C10—S1—C11—N1−172.8 (3)C13—C12—N2—C110.0 (6)
N2—C12—C13—C140.6 (7)C16—C15—N3—C191.3 (7)
C12—C13—C14—N1−0.7 (6)C14—C15—N3—C19−178.9 (4)
C12—C13—C14—C15176.9 (4)C18—C19—N3—C15−2.4 (9)
N1—C14—C15—N3172.9 (4)C23—C22—N4—C21−0.7 (8)
C13—C14—C15—N3−4.8 (6)N5—C21—N4—C221.3 (7)
N1—C14—C15—C16−7.2 (6)S2—C21—N4—C22−175.8 (4)
C13—C14—C15—C16175.0 (4)N4—C21—N5—C24−0.6 (7)
N3—C15—C16—C17−0.8 (7)S2—C21—N5—C24176.3 (3)
C14—C15—C16—C17179.4 (4)C23—C24—N5—C21−0.6 (7)
C15—C16—C17—C181.2 (8)C25—C24—N5—C21−179.2 (4)
C16—C17—C18—C19−2.2 (8)C28—C29—N6—C252.3 (10)
C17—C18—C19—N32.9 (9)C26—C25—N6—C29−2.7 (8)
C6—C5—C20—S294.4 (5)C24—C25—N6—C29177.0 (5)
C4—C5—C20—S2−87.7 (5)N8—C31—N7—C34−4.6 (7)
C21—S2—C20—C5−157.7 (4)S3—C31—N7—C34177.9 (3)
C20—S2—C21—N54.7 (4)C33—C34—N7—C310.3 (7)
C20—S2—C21—N4−178.0 (4)C35—C34—N7—C31179.3 (4)
N4—C22—C23—C24−0.4 (9)C33—C32—N8—C31−2.2 (8)
C22—C23—C24—N51.1 (7)N7—C31—N8—C325.4 (7)
C22—C23—C24—C25179.6 (5)S3—C31—N8—C32−177.2 (4)
N5—C24—C25—N6180.0 (5)C36—C35—N9—C390.1 (7)
C23—C24—C25—N61.5 (7)C34—C35—N9—C39−179.8 (4)
N5—C24—C25—C26−0.3 (7)C38—C39—N9—C351.0 (8)
C23—C24—C25—C26−178.8 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C20—H20A···N50.972.392.818 (6)106
C26—H26A···N50.932.452.767 (7)100
C36—H36A···N70.932.492.806 (7)100

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2991).

References

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