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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1426.
Published online 2009 May 29. doi:  10.1107/S1600536809019230
PMCID: PMC2969711

2,6-Bis(2-hydroxy­ethyl)-8b,8c-diphenyl­perhydro-2,3a,4a,6,7a,8a-hexa­azacyclo­penta­[def]fluorene-4,8-dithione

Abstract

In the title mol­ecule, C24H28N6O2S2, the dihedral angle between the aromatic ring planes is 42.2 (1)°. In the crystal structure, the hydr­oxy groups are involved in O—H(...)S hydrogen bonding, which links the mol­ecules into corrugated layers propagating parallel to the bc plane.

Related literature

For the preparation of the title compound, see: Li et al. (2006 [triangle]); Broan et al. (1989 [triangle]). For general background regarding glycol­uril and its derivatives, see Gao et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1426-scheme1.jpg

Experimental

Crystal data

  • C24H28N6O2S2
  • M r = 496.64
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1426-efi1.jpg
  • a = 10.8207 (3) Å
  • b = 11.9259 (3) Å
  • c = 18.7222 (5) Å
  • β = 95.917 (1)°
  • V = 2403.16 (11) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.26 mm−1
  • T = 295 K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick,1996 [triangle]) T min = 0.927, T max = 0.975
  • 26638 measured reflections
  • 5248 independent reflections
  • 3908 reflections with I > 2σ(I)
  • R int = 0.048

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.141
  • S = 1.04
  • 5248 reflections
  • 313 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.43 e Å−3
  • Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [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/S1600536809019230/cv2558sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019230/cv2558Isup2.hkl

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

Acknowledgments

The authors thank Professor An-Xin Wu for technical assistance and Dr Xiang-Gao Meng for the data collection.

supplementary crystallographic information

Comment

The rigid concave shape of glycoluril makes it a versatile building block to construct various supramolecular objects (Gao et al., 2009). We report here the structure of the title thioglycoluril derivative (Fig. 1), which is a potential receptor in supramolecular chemistry.

The title compound, C24H28N6O2S2, is a thioglycoluril derivative. The crystal packing is stabilized by intermolecular O–H···S hydrogen bonds (Table 1).

Experimental

The title compound was synthesized according to the procedure reported (Broan et al., 1989; Li et al., 2006). Crystals appropriate for X-ray data collection were obtained by slow evaporation of the dichloromethane solution at 293 K.

Refinement

C-bound H atoms were positioned in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å and Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(C). The hydroxyl H atoms were found from the Fourier difference map and refined with the bond restraint O—H = 0.82 (2) Å, and Uiso(H) = 1.5Ueq(O).

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C24H28N6O2S2F(000) = 1048
Mr = 496.64Dx = 1.373 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7811 reflections
a = 10.8207 (3) Åθ = 2.6–26.8°
b = 11.9259 (3) ŵ = 0.26 mm1
c = 18.7222 (5) ÅT = 295 K
β = 95.917 (1)°Block, colorless
V = 2403.16 (11) Å30.30 × 0.20 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer5248 independent reflections
Radiation source: fine-focus sealed tube3908 reflections with I > 2σ(I)
graphiteRint = 0.048
[var phi] and ω scansθmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick,1996)h = −13→13
Tmin = 0.927, Tmax = 0.975k = −15→14
26638 measured reflectionsl = −23→23

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) = 0.141H atoms treated by a mixture of independent and constrained refinement
S = 1.04w = 1/[σ2(Fo2) + (0.086P)2] where P = (Fo2 + 2Fc2)/3
5248 reflections(Δ/σ)max < 0.001
313 parametersΔρmax = 0.43 e Å3
2 restraintsΔρmin = −0.31 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
C1−0.12009 (19)0.06722 (19)0.17347 (12)0.0556 (6)
H1A−0.12470.12950.20640.067*
H1B−0.18350.07840.13360.067*
C20.00508 (18)0.06743 (18)0.14581 (10)0.0468 (5)
H2A0.01410.00010.11770.056*
H2B0.01130.13160.11460.056*
C30.22092 (19)0.02137 (15)0.18881 (10)0.0423 (5)
H3A0.2027−0.05080.16630.051*
H3B0.27350.00840.23320.051*
C40.12806 (17)0.18506 (15)0.23345 (9)0.0389 (4)
H4A0.17700.18120.27980.047*
H4B0.04910.21990.24030.047*
C50.27962 (17)0.08201 (15)0.06750 (10)0.0376 (4)
C60.14142 (15)0.32561 (14)0.13366 (9)0.0322 (4)
C70.31088 (15)0.20650 (13)0.16475 (9)0.0302 (4)
C80.41469 (15)0.21794 (15)0.22511 (9)0.0350 (4)
C90.51836 (17)0.14859 (17)0.22663 (11)0.0459 (5)
H90.52090.09140.19300.055*
C100.61795 (18)0.1651 (2)0.27853 (13)0.0579 (6)
H100.68820.12010.27900.070*
C110.6129 (2)0.2475 (2)0.32904 (13)0.0617 (6)
H110.67940.25750.36410.074*
C120.5107 (2)0.31542 (19)0.32845 (12)0.0566 (6)
H120.50790.37090.36320.068*
C130.41094 (18)0.30164 (16)0.27611 (10)0.0428 (4)
H130.34200.34840.27540.051*
C140.32978 (15)0.26964 (13)0.09338 (9)0.0318 (4)
C150.45229 (15)0.33084 (15)0.09195 (9)0.0354 (4)
C160.55620 (18)0.27555 (18)0.07309 (12)0.0510 (5)
H160.54940.20250.05570.061*
C170.67082 (19)0.3290 (2)0.08007 (13)0.0599 (6)
H170.74080.29140.06760.072*
C180.68142 (19)0.4367 (2)0.10520 (13)0.0577 (6)
H180.75890.47120.11070.069*
C190.5778 (2)0.49443 (19)0.12239 (12)0.0523 (5)
H190.58480.56820.13840.063*
C200.46311 (17)0.44085 (16)0.11538 (11)0.0441 (5)
H200.39290.47930.12660.053*
C210.28287 (19)0.22150 (17)−0.03467 (10)0.0464 (5)
H21A0.35400.2611−0.04980.056*
H21B0.26620.1576−0.06630.056*
C220.19164 (19)0.38613 (15)0.01067 (11)0.0428 (5)
H22A0.11560.42960.00860.051*
H22B0.25730.4354−0.00190.051*
C230.0576 (2)0.23381 (17)−0.04220 (12)0.0537 (6)
H23A0.04910.20730.00600.064*
H23B0.06100.1686−0.07290.064*
C24−0.0547 (2)0.3012 (2)−0.06773 (14)0.0681 (7)
H24A−0.12810.2574−0.06100.082*
H24B−0.05630.3676−0.03790.082*
N10.10632 (14)0.07216 (13)0.20529 (8)0.0414 (4)
N20.28966 (13)0.09106 (11)0.14054 (8)0.0342 (3)
N30.19398 (12)0.25404 (12)0.18405 (7)0.0319 (3)
N40.31342 (14)0.18107 (12)0.03940 (8)0.0373 (4)
N50.22274 (13)0.34526 (12)0.08454 (8)0.0333 (3)
N60.17545 (15)0.29589 (13)−0.04166 (8)0.0453 (4)
O1−0.14482 (17)−0.03208 (18)0.20862 (11)0.0846 (6)
H1−0.087 (2)−0.045 (3)0.2388 (15)0.127*
O2−0.0615 (2)0.33480 (17)−0.13943 (11)0.0862 (6)
H2−0.033 (3)0.3995 (15)−0.1335 (19)0.129*
S10.24080 (7)−0.03339 (4)0.02083 (3)0.0601 (2)
S20.00120 (4)0.38457 (5)0.13406 (3)0.04925 (17)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0446 (12)0.0720 (15)0.0484 (13)−0.0162 (11)−0.0034 (10)0.0076 (11)
C20.0515 (12)0.0500 (12)0.0384 (11)−0.0192 (9)0.0022 (9)−0.0006 (9)
C30.0530 (11)0.0342 (10)0.0391 (11)−0.0063 (8)0.0023 (9)0.0039 (8)
C40.0369 (10)0.0488 (11)0.0313 (10)−0.0088 (8)0.0051 (8)−0.0008 (8)
C50.0393 (10)0.0346 (9)0.0388 (11)0.0028 (8)0.0031 (8)−0.0017 (8)
C60.0281 (8)0.0316 (9)0.0361 (10)−0.0041 (7)−0.0006 (7)−0.0059 (7)
C70.0279 (8)0.0303 (8)0.0323 (9)0.0002 (6)0.0028 (7)−0.0009 (7)
C80.0301 (9)0.0389 (10)0.0354 (10)−0.0043 (7)0.0008 (7)0.0055 (8)
C90.0360 (10)0.0533 (12)0.0481 (12)0.0027 (9)0.0033 (9)0.0075 (9)
C100.0316 (10)0.0721 (15)0.0688 (16)0.0026 (10)−0.0008 (10)0.0249 (13)
C110.0438 (13)0.0765 (16)0.0600 (15)−0.0198 (11)−0.0178 (11)0.0157 (13)
C120.0595 (14)0.0585 (13)0.0485 (13)−0.0183 (11)−0.0109 (10)−0.0011 (10)
C130.0429 (10)0.0417 (10)0.0422 (11)−0.0050 (8)−0.0029 (8)−0.0009 (8)
C140.0312 (9)0.0308 (9)0.0334 (9)0.0007 (7)0.0041 (7)−0.0024 (7)
C150.0308 (9)0.0414 (10)0.0345 (10)−0.0021 (7)0.0062 (7)0.0051 (8)
C160.0398 (11)0.0517 (12)0.0636 (14)0.0056 (9)0.0155 (10)0.0069 (10)
C170.0328 (11)0.0704 (15)0.0789 (17)0.0057 (10)0.0174 (10)0.0173 (13)
C180.0323 (10)0.0753 (16)0.0647 (15)−0.0137 (10)0.0008 (10)0.0233 (12)
C190.0448 (11)0.0550 (12)0.0564 (13)−0.0150 (10)0.0016 (9)0.0039 (10)
C200.0344 (10)0.0466 (11)0.0513 (12)−0.0054 (8)0.0050 (8)−0.0008 (9)
C210.0574 (13)0.0478 (11)0.0348 (11)−0.0032 (9)0.0079 (9)−0.0012 (9)
C220.0426 (10)0.0369 (10)0.0479 (12)−0.0023 (8)−0.0005 (9)0.0099 (9)
C230.0595 (14)0.0503 (12)0.0481 (13)−0.0145 (10)−0.0098 (10)0.0072 (10)
C240.0584 (15)0.0822 (17)0.0611 (16)−0.0197 (13)−0.0068 (12)0.0089 (13)
N10.0435 (9)0.0430 (9)0.0375 (9)−0.0118 (7)0.0032 (7)0.0011 (7)
N20.0400 (8)0.0283 (7)0.0341 (8)−0.0022 (6)0.0027 (6)−0.0023 (6)
N30.0258 (7)0.0364 (8)0.0337 (8)−0.0021 (6)0.0043 (6)−0.0027 (6)
N40.0446 (9)0.0356 (8)0.0323 (8)−0.0011 (7)0.0062 (7)−0.0035 (6)
N50.0281 (7)0.0341 (8)0.0374 (8)0.0006 (6)0.0011 (6)0.0034 (6)
N60.0508 (10)0.0446 (9)0.0390 (9)−0.0074 (7)−0.0022 (7)0.0054 (7)
O10.0646 (12)0.1027 (14)0.0842 (14)−0.0396 (11)−0.0034 (9)0.0390 (11)
O20.0899 (14)0.0982 (15)0.0647 (12)−0.0084 (12)−0.0198 (10)0.0193 (11)
S10.0926 (5)0.0386 (3)0.0479 (4)−0.0061 (3)0.0013 (3)−0.0121 (2)
S20.0294 (3)0.0545 (3)0.0636 (4)0.0086 (2)0.0036 (2)−0.0030 (3)

Geometric parameters (Å, °)

C1—O11.394 (3)C12—H120.9300
C1—C21.499 (3)C13—H130.9300
C1—H1A0.9700C14—N41.460 (2)
C1—H1B0.9700C14—N51.464 (2)
C2—N11.481 (3)C14—C151.516 (2)
C2—H2A0.9700C15—C161.380 (2)
C2—H2B0.9700C15—C201.384 (3)
C3—N11.442 (2)C16—C171.388 (3)
C3—N21.483 (2)C16—H160.9300
C3—H3A0.9700C17—C181.369 (3)
C3—H3B0.9700C17—H170.9300
C4—N11.456 (2)C18—C191.381 (3)
C4—N31.476 (2)C18—H180.9300
C4—H4A0.9700C19—C201.390 (3)
C4—H4B0.9700C19—H190.9300
C5—N41.359 (2)C20—H200.9300
C5—N21.365 (2)C21—N61.457 (2)
C5—S11.6609 (19)C21—N41.473 (2)
C6—N31.353 (2)C21—H21A0.9700
C6—N51.357 (2)C21—H21B0.9700
C6—S21.6730 (17)C22—N61.454 (2)
C7—N21.460 (2)C22—N51.472 (2)
C7—N31.465 (2)C22—H22A0.9700
C7—C81.515 (2)C22—H22B0.9700
C7—C141.565 (2)C23—N61.474 (2)
C8—C131.385 (3)C23—C241.494 (3)
C8—C91.392 (3)C23—H23A0.9700
C9—C101.389 (3)C23—H23B0.9700
C9—H90.9300C24—O21.395 (3)
C10—C111.369 (3)C24—H24A0.9700
C10—H100.9300C24—H24B0.9700
C11—C121.370 (3)O1—H10.81 (2)
C11—H110.9300O2—H20.83 (2)
C12—C131.390 (3)
O1—C1—C2112.9 (2)C16—C15—C14120.75 (16)
O1—C1—H1A109.0C20—C15—C14119.75 (15)
C2—C1—H1A109.0C15—C16—C17120.0 (2)
O1—C1—H1B109.0C15—C16—H16120.0
C2—C1—H1B109.0C17—C16—H16120.0
H1A—C1—H1B107.8C18—C17—C16120.3 (2)
N1—C2—C1111.41 (16)C18—C17—H17119.8
N1—C2—H2A109.3C16—C17—H17119.8
C1—C2—H2A109.3C17—C18—C19120.44 (19)
N1—C2—H2B109.3C17—C18—H18119.8
C1—C2—H2B109.3C19—C18—H18119.8
H2A—C2—H2B108.0C18—C19—C20119.1 (2)
N1—C3—N2113.05 (14)C18—C19—H19120.4
N1—C3—H3A109.0C20—C19—H19120.4
N2—C3—H3A109.0C15—C20—C19120.72 (19)
N1—C3—H3B109.0C15—C20—H20119.6
N2—C3—H3B109.0C19—C20—H20119.6
H3A—C3—H3B107.8N6—C21—N4112.54 (15)
N1—C4—N3111.04 (13)N6—C21—H21A109.1
N1—C4—H4A109.4N4—C21—H21A109.1
N3—C4—H4A109.4N6—C21—H21B109.1
N1—C4—H4B109.4N4—C21—H21B109.1
N3—C4—H4B109.4H21A—C21—H21B107.8
H4A—C4—H4B108.0N6—C22—N5112.82 (14)
N4—C5—N2108.81 (15)N6—C22—H22A109.0
N4—C5—S1125.48 (14)N5—C22—H22A109.0
N2—C5—S1125.61 (14)N6—C22—H22B109.0
N3—C6—N5109.03 (14)N5—C22—H22B109.0
N3—C6—S2125.32 (13)H22A—C22—H22B107.8
N5—C6—S2125.60 (13)N6—C23—C24113.98 (18)
N2—C7—N3109.23 (13)N6—C23—H23A108.8
N2—C7—C8113.40 (14)C24—C23—H23A108.8
N3—C7—C8111.95 (13)N6—C23—H23B108.8
N2—C7—C14102.63 (13)C24—C23—H23B108.8
N3—C7—C14102.50 (13)H23A—C23—H23B107.7
C8—C7—C14116.19 (13)O2—C24—C23115.0 (2)
C13—C8—C9119.68 (17)O2—C24—H24A108.5
C13—C8—C7120.47 (16)C23—C24—H24A108.5
C9—C8—C7119.72 (16)O2—C24—H24B108.5
C10—C9—C8119.7 (2)C23—C24—H24B108.5
C10—C9—H9120.1H24A—C24—H24B107.5
C8—C9—H9120.1C3—N1—C4110.83 (14)
C11—C10—C9120.1 (2)C3—N1—C2114.15 (15)
C11—C10—H10119.9C4—N1—C2112.76 (15)
C9—C10—H10119.9C5—N2—C7112.29 (14)
C10—C11—C12120.6 (2)C5—N2—C3124.97 (15)
C10—C11—H11119.7C7—N2—C3114.32 (13)
C12—C11—H11119.7C6—N3—C7112.56 (13)
C11—C12—C13120.2 (2)C6—N3—C4126.37 (14)
C11—C12—H12119.9C7—N3—C4115.11 (13)
C13—C12—H12119.9C5—N4—C14112.29 (14)
C8—C13—C12119.69 (19)C5—N4—C21127.29 (15)
C8—C13—H13120.2C14—N4—C21114.47 (14)
C12—C13—H13120.2C6—N5—C14112.19 (14)
N4—C14—N5109.23 (14)C6—N5—C22126.32 (14)
N4—C14—C15112.33 (13)C14—N5—C22114.32 (14)
N5—C14—C15112.61 (13)C22—N6—C21110.52 (15)
N4—C14—C7103.04 (13)C22—N6—C23114.88 (16)
N5—C14—C7102.79 (12)C21—N6—C23112.11 (16)
C15—C14—C7115.99 (14)C1—O1—H1108 (3)
C16—C15—C20119.29 (17)C24—O2—H299 (3)
O1—C1—C2—N1−69.4 (2)C8—C7—N2—C5−133.09 (15)
N2—C7—C8—C13−148.92 (15)C14—C7—N2—C5−6.95 (17)
N3—C7—C8—C13−24.8 (2)N3—C7—N2—C3−48.59 (19)
C14—C7—C8—C1392.50 (19)C8—C7—N2—C377.02 (18)
N2—C7—C8—C935.3 (2)C14—C7—N2—C3−156.84 (14)
N3—C7—C8—C9159.47 (15)N1—C3—N2—C5−93.2 (2)
C14—C7—C8—C9−83.3 (2)N1—C3—N2—C752.3 (2)
C13—C8—C9—C10−1.1 (3)N5—C6—N3—C7−9.10 (19)
C7—C8—C9—C10174.74 (17)S2—C6—N3—C7173.37 (12)
C8—C9—C10—C111.6 (3)N5—C6—N3—C4−160.35 (15)
C9—C10—C11—C12−0.9 (3)S2—C6—N3—C422.1 (2)
C10—C11—C12—C13−0.4 (3)N2—C7—N3—C6−103.97 (15)
C9—C8—C13—C12−0.2 (3)C8—C7—N3—C6129.58 (15)
C7—C8—C13—C12−175.92 (17)C14—C7—N3—C64.36 (17)
C11—C12—C13—C80.9 (3)N2—C7—N3—C450.70 (18)
N2—C7—C14—N41.33 (15)C8—C7—N3—C4−75.75 (17)
N3—C7—C14—N4−111.96 (13)C14—C7—N3—C4159.04 (13)
C8—C7—C14—N4125.65 (15)N1—C4—N3—C695.90 (19)
N2—C7—C14—N5114.86 (13)N1—C4—N3—C7−54.72 (19)
N3—C7—C14—N51.57 (15)N2—C5—N4—C14−9.2 (2)
C8—C7—C14—N5−120.81 (15)S1—C5—N4—C14174.18 (13)
N2—C7—C14—C15−121.82 (15)N2—C5—N4—C21−160.26 (16)
N3—C7—C14—C15124.89 (14)S1—C5—N4—C2123.2 (3)
C8—C7—C14—C152.5 (2)N5—C14—N4—C5−104.12 (16)
N4—C14—C15—C16−32.1 (2)C15—C14—N4—C5130.19 (16)
N5—C14—C15—C16−155.98 (17)C7—C14—N4—C54.64 (18)
C7—C14—C15—C1686.0 (2)N5—C14—N4—C2150.83 (18)
N4—C14—C15—C20153.17 (17)C15—C14—N4—C21−74.86 (18)
N5—C14—C15—C2029.3 (2)C7—C14—N4—C21159.59 (14)
C7—C14—C15—C20−88.7 (2)N6—C21—N4—C596.9 (2)
C20—C15—C16—C172.2 (3)N6—C21—N4—C14−53.6 (2)
C14—C15—C16—C17−172.49 (19)N3—C6—N5—C1410.25 (19)
C15—C16—C17—C18−0.4 (3)S2—C6—N5—C14−172.23 (12)
C16—C17—C18—C19−1.5 (4)N3—C6—N5—C22158.67 (15)
C17—C18—C19—C201.5 (3)S2—C6—N5—C22−23.8 (2)
C16—C15—C20—C19−2.2 (3)N4—C14—N5—C6101.81 (16)
C14—C15—C20—C19172.53 (18)C15—C14—N5—C6−132.65 (15)
C18—C19—C20—C150.4 (3)C7—C14—N5—C6−7.11 (17)
N6—C23—C24—O265.1 (3)N4—C14—N5—C22−50.61 (18)
N2—C3—N1—C4−53.7 (2)C15—C14—N5—C2274.93 (18)
N2—C3—N1—C274.92 (19)C7—C14—N5—C22−159.53 (13)
N3—C4—N1—C354.3 (2)N6—C22—N5—C6−94.4 (2)
N3—C4—N1—C2−75.12 (18)N6—C22—N5—C1453.41 (19)
C1—C2—N1—C3152.21 (17)N5—C22—N6—C21−52.6 (2)
C1—C2—N1—C4−80.1 (2)N5—C22—N6—C2375.5 (2)
N4—C5—N2—C710.2 (2)N4—C21—N6—C2252.5 (2)
S1—C5—N2—C7−173.19 (13)N4—C21—N6—C23−77.0 (2)
N4—C5—N2—C3156.33 (16)C24—C23—N6—C2267.6 (2)
S1—C5—N2—C3−27.1 (3)C24—C23—N6—C21−165.17 (18)
N3—C7—N2—C5101.30 (16)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···S2i0.81 (2)2.61 (2)3.337 (2)151 (3)
O2—H2···S2ii0.83 (2)2.60 (1)3.409 (2)165 (4)

Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) −x, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2558).

References

  • Broan, C. J., Butler, A. R., Reed, D. & Sadler, I. H. (1989). J. Chem. Soc. Perkin Trans. 2, pp. 731–740.
  • Bruker (2001). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Gao, M., Cao, L., Wang, Z., Sun, J., She, N. & Wu, A. (2009). Synlett, pp. 315–319.
  • Li, Y., Yin, G., Guo, H., Zhou, B. & Wu, A. (2006). Synthesis, pp. 2897–2902.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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