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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): o1022–o1023.
Published online 2008 May 10. doi:  10.1107/S160053680801297X
PMCID: PMC2961618

(E)-2-[1-(1-Benzothio­phen-3-yl)ethyl­idene]hydrazinecarbothio­amide methanol hemisolvate

Abstract

The asymmetric unit of the title compound, C11H11N3S2·0.5CH4O, contains four thio­semicarbazone mol­ecules and two methanol solvent mol­ecules. Each hydrazinecarbothio­amide mol­ecule adopts an E configuration with respect to the C=N double bond and is stabilized by an intra­molecular N—H(...)N hydrogen bond, resulting in an S(5) ring motif. In the crystal structure, an extensive network of N—H(...)O, N—H(...)N, O—H(...)S and N—H(...)S hydrogen bonds and weak C—H(...)O, C—H(...)N and C—H(...)S contacts together with an S(...)S [3.5958 (14) Å] and a C—H(...)π inter­action form a three-dimensional network.

Related literature

For related structures, see: de Lima et al. (2002 [triangle]); Işık et al. (2006 [triangle]). For reference structural data, see: Allen et al. (1987 [triangle]). For graph-set analysis of hydrogen bonding, see: Bernstein et al., (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1022-scheme1.jpg

Experimental

Crystal data

  • C11H11N3S2·0.5CH4O
  • M r = 265.38
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1022-efi1.jpg
  • a = 18.9438 (12) Å
  • b = 17.7076 (11) Å
  • c = 15.4145 (10) Å
  • β = 107.238 (3)°
  • V = 4938.5 (5) Å3
  • Z = 16
  • Mo Kα radiation
  • μ = 0.41 mm−1
  • T = 92 (2) K
  • 0.31 × 0.20 × 0.13 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2006 [triangle]) T min = 0.777, T max = 0.947
  • 65034 measured reflections
  • 10871 independent reflections
  • 8171 reflections with I > 2σ(I)
  • R int = 0.086

Refinement

  • R[F 2 > 2σ(F 2)] = 0.067
  • wR(F 2) = 0.203
  • S = 1.03
  • 10871 reflections
  • 655 parameters
  • 12 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 1.71 e Å−3
  • Δρmin = −2.31 e Å−3

Data collection: APEX2 (Bruker, 2006 [triangle]); cell refinement: APEX2 and SAINT (Bruker, 2006 [triangle]); data reduction: SAINT (Bruker, 2006 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]) and TITAN2000 (Hunter & Simpson, 1999 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]) and TITAN2000; molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]), ORTEP-3 (Farrugia, 1997 [triangle]) and Mercury (Macrae et al., 2006 [triangle]); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 [triangle]) and PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801297X/hb2725sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801297X/hb2725Isup2.hkl

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

Acknowledgments

We thank the Universiti Kebangsaan Malaysia and the Ministry of Higher Education, Malaysia, for supporting this research through grant UKM-ST-01-FRGS0022-2006. We also thank the University of Otago for the purchase of the diffractometer.

supplementary crystallographic information

Comment

Structures similar to the title compound, (I), have been reported including the thiosemicarbazone derived from 2-acetylthiophene (Lima et al., 2002); and a pryazoline derivative (Işık et al., 2006).

The asymmetric unit of (I) contains four molecules, labeled A—D (Figs 1—4) and two methanol solvate molecules, with the complete assemblage shown in Fig. 5. Each molecule adopts an E configuration with respect to the C=N bond and bond distances and angles are normal (Allen et al., 1987). Intramolecular N3—H···N1 hydrogen bonds (Table 1) form between each of the the NH2 groups and the imine N atoms generating S(5) ring motifs (Bernstein et al., 1995). These contribute to the planarity of the molecules.

In the crystal of (I), N2—H2···S2 hydrogen bonds generate centrosymmetric R22(8) rings in molecules A—C. For molecule D, C2S—H2S1···S2D hydrogen bonding to a methanol solvate within the asymmetric unit obviates such an interaction. Other N—H···O, N—H···N, O—H···S and N—H···S hydrogen bonds together with weak C—H···O, C—H···N and C—H···S contacts, an S···S interaction (d(S1D···S1Bi) = 3.5958 (14) Å; i = x, 3/2 - y, -1/2 + z) and a C10B—H10F···Cgii interaction (ii = -x, 1 - y, -z; Cg is the centroid of the C1B···C6B ring) form a complex three dimensional network (Fig 6).

Experimental

A 1:1 mixture of 2-acetylbenzothiophene and thiosemicarbazide was heated under reflux in ethanol for 2 h. The solid product which separated upon cooling was filtered and recrystallized from a 1:1 mixture of acetonitrile and methanol to afford colourless, blocks of (I) in 68% yield (m.p. 483–485 K).

Refinement

The C-bound H atoms were placed geometrically (C—H = 0.95-0.98Å) and refined as riding with Uiso=1.2Ueq(C) of 1.5Ueq(methyl C).

The N-bound H atoms were located in a difference map and refined with a distance restraint of N—H = 0.84 (1) Å, and with Uiso(H) = 1.2Ueq(N) (carrier).

The highest residual electron density peak is 0.07 Å from O2S and the deepest hole is 0.04Å from C2S suggesting the possibility of unresolved disorder in this methanol solvate molecule.

Figures

Fig. 1.
The structure of molecule A in (I) showing 50% probability displacement ellipsoids for the non-H atoms. The intramolecular N—H···N hydrogen bond is drawn as a dashed line.
Fig. 2.
The structure of molecule B in (I) showing 50% probability displacement ellipsoids for the non-H atoms. The intramolecular N—H···N hydrogen bond is drawn as a dashed line.
Fig. 3.
The structure of molecule C in (I) showing 50% probability displacement ellipsoids for the non-H atoms. The intramolecular N—H···N hydrogen bond is drawn as a dashed line.
Fig. 4.
The structure of molecule D in (I) showing 50% probability displacement ellipsoids for the non-H atoms. The intramolecular N—H···N hydrogen bond is drawn as a dashed line.
Fig. 5.
The asymmetric unit of (I) with intermolecular hydrogen bonds drawn as dashed lines.
Fig. 6.
Crystal packing of (I) viewed down the a axis with hydrogen bonds drawn as dashed lines.

Crystal data

C11H11N3S2·0.5(CH4O)F000 = 2224
Mr = 265.38Dx = 1.428 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8980 reflections
a = 18.9438 (12) Åθ = 2.3–25.6º
b = 17.7076 (11) ŵ = 0.42 mm1
c = 15.4145 (10) ÅT = 92 (2) K
β = 107.238 (3)ºBlock, colourless
V = 4938.5 (5) Å30.31 × 0.20 × 0.13 mm
Z = 16

Data collection

Bruker APEXII CCD area-detector diffractometer10871 independent reflections
Radiation source: fine-focus sealed tube8171 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.086
T = 92(2) Kθmax = 27.1º
ω scansθmin = 1.1º
Absorption correction: multi-scan(SADABS; Bruker, 2006)h = −24→24
Tmin = 0.777, Tmax = 0.947k = −22→22
65034 measured reflectionsl = −19→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.067H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.203  w = 1/[σ2(Fo2) + (0.1068P)2 + 8.4506P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
10871 reflectionsΔρmax = 1.71 e Å3
655 parametersΔρmin = −2.30 e Å3
12 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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
C1A0.40620 (18)0.50684 (18)0.8528 (2)0.0201 (7)
C2A0.36631 (19)0.44650 (19)0.8029 (2)0.0241 (7)
H2A0.37460.43000.74800.029*
C3A0.3144 (2)0.41176 (19)0.8364 (2)0.0254 (7)
H3A0.28720.37000.80460.030*
C4A0.3010 (2)0.4368 (2)0.9163 (3)0.0263 (8)
H4A0.26430.41250.93700.032*
C5A0.3402 (2)0.4960 (2)0.9651 (3)0.0252 (7)
H5A0.33090.51241.01930.030*
C6A0.39438 (18)0.53217 (18)0.9341 (2)0.0212 (7)
S1A0.47650 (5)0.55720 (5)0.82797 (6)0.0235 (2)
C7A0.44278 (18)0.59319 (19)0.9744 (2)0.0224 (7)
H7A0.44220.61761.02910.027*
C8A0.48976 (18)0.61239 (18)0.9258 (2)0.0200 (7)
C9A0.54827 (18)0.66957 (18)0.9473 (2)0.0207 (7)
C10A0.56188 (18)0.71682 (19)1.0314 (2)0.0223 (7)
H10A0.61080.70511.07290.033*
H10B0.52410.70581.06140.033*
H10C0.55960.77041.01500.033*
N1A0.58542 (15)0.67430 (16)0.8893 (2)0.0213 (6)
N2A0.64370 (16)0.72396 (16)0.9091 (2)0.0211 (6)
H2NA0.659 (2)0.743 (2)0.9613 (13)0.025*
C11A0.67880 (18)0.73726 (18)0.8465 (2)0.0194 (7)
S2A0.75517 (5)0.79377 (5)0.87472 (6)0.02159 (19)
N3A0.65198 (17)0.70631 (19)0.7655 (2)0.0261 (6)
H3N10.676 (2)0.714 (2)0.729 (2)0.031*
H3N20.6187 (17)0.6733 (18)0.758 (3)0.031*
C1B0.1144 (2)0.9732 (2)0.6666 (2)0.0259 (7)
C2B0.1682 (2)1.0138 (2)0.7312 (3)0.0377 (10)
H2B0.16761.01650.79260.045*
C3B0.2225 (2)1.0503 (2)0.7030 (3)0.0347 (9)
H3B0.25941.07870.74580.042*
C4B0.2239 (2)1.0461 (2)0.6135 (3)0.0295 (8)
H4B0.26141.07200.59590.035*
C5B0.1714 (2)1.0047 (2)0.5495 (3)0.0267 (8)
H5B0.17301.00150.48860.032*
C6B0.11558 (18)0.96745 (18)0.5761 (2)0.0213 (7)
S1B0.04048 (5)0.92419 (5)0.68465 (6)0.0294 (2)
C7B0.05600 (19)0.92149 (19)0.5224 (2)0.0227 (7)
H7B0.04840.91070.46000.027*
C8B0.01121 (18)0.89489 (18)0.5715 (2)0.0203 (7)
C9B−0.05345 (18)0.84574 (18)0.5407 (2)0.0217 (7)
C10B−0.0764 (2)0.8167 (2)0.4454 (2)0.0269 (8)
H10D−0.07630.76140.44610.040*
H10E−0.04170.83490.41380.040*
H10F−0.12620.83490.41370.040*
N1B−0.08527 (15)0.83003 (16)0.6022 (2)0.0212 (6)
N2B−0.14681 (16)0.78420 (16)0.5770 (2)0.0216 (6)
H2NB−0.166 (2)0.768 (2)0.5243 (13)0.026*
C11B−0.17783 (18)0.76294 (19)0.6424 (2)0.0202 (7)
S2B−0.25346 (5)0.70679 (5)0.61499 (6)0.0227 (2)
N3B−0.14553 (16)0.78669 (17)0.7263 (2)0.0233 (6)
H3N3−0.1059 (13)0.811 (2)0.735 (3)0.028*
H3N4−0.165 (2)0.770 (2)0.765 (2)0.028*
C1C0.3583 (2)0.7371 (2)0.6860 (2)0.0258 (7)
C2C0.4354 (2)0.7437 (2)0.7138 (3)0.0297 (8)
H2C0.46610.70020.72290.036*
C3C0.4653 (2)0.8154 (2)0.7275 (3)0.0323 (9)
H3C0.51750.82140.74660.039*
C4C0.4199 (2)0.8795 (2)0.7138 (3)0.0351 (9)
H4C0.44190.92810.72430.042*
C5C0.3439 (2)0.8733 (2)0.6853 (3)0.0351 (9)
H5C0.31380.91720.67600.042*
C6C0.3117 (2)0.8011 (2)0.6700 (2)0.0266 (8)
S1C0.30752 (5)0.65375 (5)0.66624 (7)0.0281 (2)
C7C0.2349 (2)0.7803 (2)0.6387 (3)0.0287 (8)
H7C0.19550.81580.62340.034*
C8C0.2248 (2)0.70426 (19)0.6336 (2)0.0244 (7)
C9C0.1548 (2)0.6635 (2)0.6066 (2)0.0258 (7)
C10C0.0836 (2)0.7064 (2)0.5745 (3)0.0319 (9)
H10G0.07590.72300.51170.048*
H10H0.08570.75060.61350.048*
H10I0.04260.67370.57730.048*
N1C0.16139 (17)0.59049 (17)0.6156 (2)0.0297 (7)
N2C0.09860 (18)0.54666 (18)0.5948 (2)0.0346 (8)
H2NC0.0583 (14)0.559 (3)0.556 (3)0.042*
C11C0.1060 (2)0.4744 (2)0.6250 (3)0.0298 (8)
S2C0.03402 (6)0.41383 (6)0.60223 (8)0.0448 (3)
N3C0.17357 (19)0.45564 (18)0.6749 (2)0.0322 (8)
H3N50.2098 (18)0.485 (2)0.688 (3)0.050 (15)*
H3N60.184 (3)0.4118 (12)0.696 (3)0.051 (15)*
C1D0.1294 (2)0.7575 (2)0.3394 (3)0.0292 (8)
C2D0.0537 (2)0.7729 (3)0.3080 (3)0.0398 (10)
H2D0.01810.73400.30210.048*
C3D0.0326 (3)0.8473 (3)0.2858 (3)0.0445 (11)
H3D−0.01840.85930.26360.053*
C4D0.0844 (3)0.9040 (3)0.2953 (3)0.0412 (10)
H4D0.06820.95430.27980.049*
C5D0.1592 (2)0.8893 (2)0.3268 (3)0.0347 (9)
H5D0.19400.92910.33340.042*
C6D0.1832 (2)0.8146 (2)0.3492 (2)0.0277 (8)
S1D0.16977 (5)0.66977 (5)0.37222 (7)0.0311 (2)
C7D0.2567 (2)0.7850 (2)0.3818 (2)0.0272 (8)
H7D0.30000.81490.39170.033*
C8D0.2576 (2)0.7092 (2)0.3971 (2)0.0252 (7)
C9D0.32188 (19)0.6605 (2)0.4331 (2)0.0245 (7)
C10D0.3983 (2)0.6910 (2)0.4466 (3)0.0341 (9)
H10J0.42620.68850.51120.051*
H10K0.39510.74360.42610.051*
H10L0.42340.66080.41130.051*
N1D0.30772 (17)0.59253 (17)0.4530 (2)0.0291 (7)
N2D0.36755 (19)0.54664 (19)0.4909 (3)0.0376 (8)
H2ND0.4088 (15)0.560 (3)0.486 (4)0.060 (17)*
C11D0.3565 (2)0.4790 (2)0.5254 (3)0.0313 (8)
S2D0.43168 (7)0.42374 (7)0.57328 (9)0.0476 (3)
N3D0.28874 (19)0.45965 (18)0.5210 (2)0.0317 (7)
H3N70.2536 (17)0.489 (2)0.496 (3)0.038*
H3N80.284 (3)0.4170 (13)0.542 (3)0.038 (13)*
O1S0.1306 (3)0.4894 (3)0.4258 (4)0.0888 (14)
H1S0.09440.51870.41860.133*
C1S0.1058 (5)0.4166 (4)0.4115 (5)0.087 (2)
H1S10.11500.39070.47000.130*
H1S20.13210.39030.37430.130*
H1S30.05270.41660.37990.130*
O2S0.5431 (3)0.5968 (3)0.6341 (4)0.0867 (12)
H2S0.56370.62790.60840.130*
C2S0.5875 (4)0.5453 (4)0.6686 (5)0.0867 (12)
H2S10.56900.49720.63900.130*
H2S20.59250.54170.73360.130*
H2S30.63570.55650.66040.130*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C1A0.0172 (16)0.0190 (15)0.0232 (16)0.0036 (12)0.0044 (13)0.0020 (13)
C2A0.0233 (18)0.0233 (17)0.0233 (17)0.0026 (13)0.0034 (14)0.0008 (14)
C3A0.0215 (17)0.0193 (16)0.0299 (18)0.0008 (13)−0.0009 (14)0.0008 (14)
C4A0.0233 (18)0.0225 (17)0.0321 (19)−0.0027 (14)0.0066 (15)0.0042 (14)
C5A0.0221 (17)0.0248 (17)0.0305 (18)−0.0023 (13)0.0106 (14)−0.0021 (14)
C6A0.0184 (16)0.0195 (15)0.0250 (17)0.0019 (13)0.0051 (13)0.0008 (13)
S1A0.0239 (4)0.0254 (4)0.0230 (4)−0.0015 (3)0.0099 (3)−0.0025 (3)
C7A0.0177 (16)0.0219 (16)0.0264 (17)−0.0003 (13)0.0048 (13)−0.0024 (14)
C8A0.0181 (16)0.0184 (15)0.0220 (16)0.0021 (12)0.0036 (13)0.0009 (13)
C9A0.0183 (16)0.0207 (15)0.0246 (17)0.0035 (13)0.0087 (13)0.0047 (13)
C10A0.0161 (16)0.0240 (16)0.0264 (17)−0.0022 (13)0.0058 (13)−0.0026 (14)
N1A0.0154 (13)0.0234 (14)0.0245 (14)−0.0005 (11)0.0052 (11)0.0016 (11)
N2A0.0171 (14)0.0252 (14)0.0227 (14)−0.0016 (11)0.0084 (11)0.0004 (12)
C11A0.0165 (15)0.0199 (15)0.0217 (16)0.0059 (12)0.0055 (12)0.0045 (13)
S2A0.0189 (4)0.0245 (4)0.0226 (4)−0.0021 (3)0.0080 (3)0.0015 (3)
N3A0.0196 (15)0.0372 (17)0.0234 (15)−0.0058 (13)0.0094 (12)−0.0016 (13)
C1B0.0258 (18)0.0249 (17)0.0278 (18)−0.0029 (14)0.0094 (14)−0.0011 (14)
C2B0.041 (2)0.042 (2)0.030 (2)−0.0145 (19)0.0110 (18)−0.0093 (18)
C3B0.030 (2)0.033 (2)0.040 (2)−0.0115 (16)0.0085 (17)−0.0105 (17)
C4B0.0217 (18)0.0255 (18)0.044 (2)−0.0058 (14)0.0135 (16)−0.0048 (16)
C5B0.0233 (18)0.0245 (17)0.035 (2)−0.0019 (14)0.0126 (15)−0.0027 (15)
C6B0.0189 (16)0.0187 (15)0.0256 (17)0.0002 (12)0.0055 (13)−0.0002 (13)
S1B0.0309 (5)0.0340 (5)0.0245 (4)−0.0113 (4)0.0102 (4)−0.0034 (4)
C7B0.0190 (16)0.0217 (16)0.0270 (17)−0.0013 (13)0.0061 (13)−0.0008 (14)
C8B0.0190 (16)0.0177 (15)0.0236 (16)−0.0005 (12)0.0051 (13)0.0003 (13)
C9B0.0186 (16)0.0203 (16)0.0256 (17)0.0032 (13)0.0056 (13)0.0015 (13)
C10B0.0220 (18)0.0335 (19)0.0258 (18)−0.0078 (15)0.0080 (14)−0.0050 (15)
N1B0.0161 (14)0.0225 (14)0.0252 (14)−0.0016 (11)0.0068 (11)0.0015 (11)
N2B0.0172 (14)0.0250 (14)0.0227 (14)−0.0032 (11)0.0061 (11)−0.0004 (12)
C11B0.0160 (15)0.0221 (16)0.0228 (16)0.0048 (12)0.0062 (12)0.0022 (13)
S2B0.0205 (4)0.0264 (4)0.0220 (4)−0.0052 (3)0.0075 (3)−0.0001 (3)
N3B0.0171 (14)0.0313 (16)0.0217 (14)−0.0048 (12)0.0060 (11)−0.0023 (12)
C1C0.0257 (18)0.0245 (17)0.0251 (17)−0.0020 (14)0.0045 (14)0.0001 (14)
C2C0.0250 (19)0.0319 (19)0.0292 (19)−0.0023 (15)0.0036 (15)−0.0008 (16)
C3C0.0253 (19)0.039 (2)0.031 (2)−0.0068 (16)0.0054 (16)0.0047 (17)
C4C0.038 (2)0.0288 (19)0.036 (2)−0.0118 (17)0.0081 (17)0.0033 (17)
C5C0.038 (2)0.0220 (18)0.042 (2)−0.0034 (16)0.0062 (18)0.0031 (16)
C6C0.0262 (19)0.0250 (17)0.0275 (18)−0.0027 (14)0.0061 (14)0.0033 (14)
S1C0.0214 (4)0.0215 (4)0.0368 (5)0.0010 (3)0.0014 (4)−0.0024 (4)
C7C0.0283 (19)0.0264 (18)0.0300 (19)−0.0002 (15)0.0065 (15)0.0014 (15)
C8C0.0240 (18)0.0226 (17)0.0244 (17)0.0028 (14)0.0035 (14)0.0041 (14)
C9C0.0237 (18)0.0235 (17)0.0267 (18)0.0004 (14)0.0019 (14)0.0020 (14)
C10C0.0204 (18)0.0278 (19)0.041 (2)0.0020 (14)−0.0009 (16)0.0064 (16)
N1C0.0202 (15)0.0247 (15)0.0375 (18)−0.0022 (12)−0.0019 (13)0.0025 (13)
N2C0.0241 (17)0.0233 (15)0.045 (2)−0.0010 (13)−0.0070 (14)0.0090 (14)
C11C0.030 (2)0.0226 (17)0.0310 (19)0.0027 (15)0.0001 (15)0.0013 (15)
S2C0.0349 (6)0.0298 (5)0.0523 (7)−0.0090 (4)−0.0136 (5)0.0164 (5)
N3C0.0283 (17)0.0222 (16)0.0359 (18)0.0032 (13)−0.0060 (14)0.0041 (14)
C1D0.028 (2)0.0323 (19)0.0278 (18)0.0034 (15)0.0088 (15)0.0008 (15)
C2D0.027 (2)0.054 (3)0.040 (2)0.0070 (19)0.0124 (17)0.008 (2)
C3D0.036 (2)0.057 (3)0.042 (2)0.021 (2)0.0135 (19)0.009 (2)
C4D0.050 (3)0.037 (2)0.043 (2)0.016 (2)0.023 (2)0.0097 (19)
C5D0.043 (2)0.0285 (19)0.036 (2)0.0057 (17)0.0164 (18)0.0034 (17)
C6D0.030 (2)0.0279 (18)0.0256 (18)0.0026 (15)0.0094 (15)0.0015 (15)
S1D0.0210 (5)0.0279 (5)0.0415 (5)−0.0019 (4)0.0045 (4)0.0037 (4)
C7D0.0275 (19)0.0286 (18)0.0246 (18)0.0000 (14)0.0064 (14)0.0024 (14)
C8D0.0223 (17)0.0237 (17)0.0275 (18)−0.0039 (14)0.0041 (14)−0.0005 (14)
C9D0.0198 (17)0.0278 (18)0.0239 (17)−0.0037 (14)0.0033 (13)0.0030 (14)
C10D0.0218 (19)0.0304 (19)0.046 (2)−0.0019 (15)0.0044 (17)0.0099 (18)
N1D0.0234 (16)0.0246 (15)0.0361 (17)0.0020 (12)0.0038 (13)0.0047 (13)
N2D0.0237 (17)0.0310 (17)0.057 (2)0.0019 (14)0.0092 (16)0.0149 (16)
C11D0.032 (2)0.0236 (18)0.036 (2)0.0032 (15)0.0071 (16)0.0038 (16)
S2D0.0374 (6)0.0426 (6)0.0628 (8)0.0165 (5)0.0150 (5)0.0240 (6)
N3D0.0286 (18)0.0218 (15)0.045 (2)0.0031 (13)0.0112 (15)0.0087 (14)
O1S0.089 (4)0.094 (4)0.089 (3)0.009 (3)0.035 (3)−0.003 (3)
C1S0.111 (6)0.074 (5)0.080 (5)−0.010 (4)0.034 (4)−0.018 (4)
O2S0.099 (3)0.064 (2)0.097 (3)0.013 (2)0.030 (2)−0.002 (2)
C2S0.099 (3)0.064 (2)0.097 (3)0.013 (2)0.030 (2)−0.002 (2)

Geometric parameters (Å, °)

C1A—C2A1.400 (5)C3C—H3C0.9500
C1A—C6A1.410 (5)C4C—C5C1.379 (6)
C1A—S1A1.737 (3)C4C—H4C0.9500
C2A—C3A1.384 (5)C5C—C6C1.406 (5)
C2A—H2A0.9500C5C—H5C0.9500
C3A—C4A1.400 (5)C6C—C7C1.439 (5)
C3A—H3A0.9500S1C—C8C1.744 (4)
C4A—C5A1.373 (5)C7C—C8C1.359 (5)
C4A—H4A0.9500C7C—H7C0.9500
C5A—C6A1.407 (5)C8C—C9C1.458 (5)
C5A—H5A0.9500C9C—N1C1.303 (5)
C6A—C7A1.434 (5)C9C—C10C1.499 (5)
S1A—C8A1.751 (3)C10C—H10G0.9800
C7A—C8A1.366 (5)C10C—H10H0.9800
C7A—H7A0.9500C10C—H10I0.9800
C8A—C9A1.465 (5)N1C—N2C1.376 (4)
C9A—N1A1.294 (4)N2C—C11C1.355 (5)
C9A—C10A1.501 (5)N2C—H2NC0.842 (10)
C10A—H10A0.9800C11C—N3C1.326 (5)
C10A—H10B0.9800C11C—S2C1.687 (4)
C10A—H10C0.9800N3C—H3N50.842 (10)
N1A—N2A1.373 (4)N3C—H3N60.840 (10)
N2A—C11A1.346 (4)C1D—C2D1.396 (5)
N2A—H2NA0.841 (10)C1D—C6D1.412 (5)
C11A—N3A1.319 (4)C1D—S1D1.740 (4)
C11A—S2A1.706 (3)C2D—C3D1.390 (6)
N3A—H3N10.839 (10)C2D—H2D0.9500
N3A—H3N20.843 (10)C3D—C4D1.382 (7)
C1B—C2B1.395 (5)C3D—H3D0.9500
C1B—C6B1.405 (5)C4D—C5D1.379 (6)
C1B—S1B1.739 (4)C4D—H4D0.9500
C2B—C3B1.390 (6)C5D—C6D1.408 (5)
C2B—H2B0.9500C5D—H5D0.9500
C3B—C4B1.390 (6)C6D—C7D1.432 (5)
C3B—H3B0.9500S1D—C8D1.739 (4)
C4B—C5B1.386 (5)S1D—S1Bi3.5958 (14)
C4B—H4B0.9500C7D—C8D1.362 (5)
C5B—C6B1.407 (5)C7D—H7D0.9500
C5B—H5B0.9500C8D—C9D1.461 (5)
C6B—C7B1.438 (5)C9D—N1D1.290 (5)
S1B—C8B1.746 (3)C9D—C10D1.500 (5)
C7B—C8B1.376 (5)C10D—H10J0.9800
C7B—H7B0.9500C10D—H10K0.9800
C8B—C9B1.462 (5)C10D—H10L0.9800
C9B—N1B1.296 (5)N1D—N2D1.376 (4)
C9B—C10B1.495 (5)N2D—C11D1.352 (5)
C10B—H10D0.9800N2D—H2ND0.842 (10)
C10B—H10E0.9800C11D—N3D1.311 (5)
C10B—H10F0.9800C11D—S2D1.705 (4)
N1B—N2B1.379 (4)N3D—H3N70.841 (10)
N2B—C11B1.362 (4)N3D—H3N80.840 (10)
N2B—H2NB0.839 (10)O1S—C1S1.367 (8)
C11B—N3B1.325 (4)O1S—H1S0.8400
C11B—S2B1.692 (3)C1S—H1S10.9800
N3B—H3N30.838 (10)C1S—H1S20.9800
N3B—H3N40.839 (10)C1S—H1S30.9800
C1C—C2C1.399 (5)O2S—C2S1.248 (8)
C1C—C6C1.413 (5)O2S—H2S0.8400
C1C—S1C1.738 (4)C2S—H2S10.9800
C2C—C3C1.381 (5)C2S—H2S20.9800
C2C—H2C0.9500C2S—H2S30.9800
C3C—C4C1.401 (6)
C2A—C1A—C6A121.9 (3)C4C—C3C—H3C119.5
C2A—C1A—S1A126.5 (3)C5C—C4C—C3C121.3 (4)
C6A—C1A—S1A111.5 (2)C5C—C4C—H4C119.3
C3A—C2A—C1A117.5 (3)C3C—C4C—H4C119.3
C3A—C2A—H2A121.3C4C—C5C—C6C119.0 (4)
C1A—C2A—H2A121.3C4C—C5C—H5C120.5
C2A—C3A—C4A121.4 (3)C6C—C5C—H5C120.5
C2A—C3A—H3A119.3C5C—C6C—C1C118.9 (3)
C4A—C3A—H3A119.3C5C—C6C—C7C129.4 (4)
C5A—C4A—C3A120.9 (3)C1C—C6C—C7C111.7 (3)
C5A—C4A—H4A119.5C1C—S1C—C8C91.05 (17)
C3A—C4A—H4A119.5C8C—C7C—C6C112.6 (3)
C4A—C5A—C6A119.5 (3)C8C—C7C—H7C123.7
C4A—C5A—H5A120.3C6C—C7C—H7C123.7
C6A—C5A—H5A120.3C7C—C8C—C9C127.4 (3)
C5A—C6A—C1A118.7 (3)C7C—C8C—S1C113.1 (3)
C5A—C6A—C7A129.2 (3)C9C—C8C—S1C119.5 (3)
C1A—C6A—C7A112.1 (3)N1C—C9C—C8C114.2 (3)
C1A—S1A—C8A91.19 (16)N1C—C9C—C10C125.9 (3)
C8A—C7A—C6A112.7 (3)C8C—C9C—C10C119.8 (3)
C8A—C7A—H7A123.6C9C—C10C—H10G109.5
C6A—C7A—H7A123.6C9C—C10C—H10H109.5
C7A—C8A—C9A128.3 (3)H10G—C10C—H10H109.5
C7A—C8A—S1A112.5 (3)C9C—C10C—H10I109.5
C9A—C8A—S1A119.1 (3)H10G—C10C—H10I109.5
N1A—C9A—C8A114.7 (3)H10H—C10C—H10I109.5
N1A—C9A—C10A124.9 (3)C9C—N1C—N2C119.1 (3)
C8A—C9A—C10A120.4 (3)C11C—N2C—N1C117.3 (3)
C9A—C10A—H10A109.5C11C—N2C—H2NC117 (3)
C9A—C10A—H10B109.5N1C—N2C—H2NC124 (3)
H10A—C10A—H10B109.5N3C—C11C—N2C114.8 (3)
C9A—C10A—H10C109.5N3C—C11C—S2C122.9 (3)
H10A—C10A—H10C109.5N2C—C11C—S2C122.3 (3)
H10B—C10A—H10C109.5C11C—N3C—H3N5124 (4)
C9A—N1A—N2A117.0 (3)C11C—N3C—H3N6122 (4)
C11A—N2A—N1A119.2 (3)H3N5—N3C—H3N6114 (5)
C11A—N2A—H2NA120 (3)C2D—C1D—C6D122.1 (4)
N1A—N2A—H2NA120 (3)C2D—C1D—S1D126.4 (3)
N3A—C11A—N2A118.2 (3)C6D—C1D—S1D111.5 (3)
N3A—C11A—S2A123.0 (3)C3D—C2D—C1D117.4 (4)
N2A—C11A—S2A118.8 (3)C3D—C2D—H2D121.3
C11A—N3A—H3N1116 (3)C1D—C2D—H2D121.3
C11A—N3A—H3N2119 (3)C4D—C3D—C2D121.3 (4)
H3N1—N3A—H3N2124 (4)C4D—C3D—H3D119.3
C2B—C1B—C6B121.5 (3)C2D—C3D—H3D119.3
C2B—C1B—S1B126.5 (3)C5D—C4D—C3D121.5 (4)
C6B—C1B—S1B111.9 (3)C5D—C4D—H4D119.2
C3B—C2B—C1B117.9 (4)C3D—C4D—H4D119.2
C3B—C2B—H2B121.0C4D—C5D—C6D119.2 (4)
C1B—C2B—H2B121.0C4D—C5D—H5D120.4
C2B—C3B—C4B121.3 (4)C6D—C5D—H5D120.4
C2B—C3B—H3B119.4C5D—C6D—C1D118.4 (4)
C4B—C3B—H3B119.4C5D—C6D—C7D129.8 (4)
C5B—C4B—C3B120.9 (4)C1D—C6D—C7D111.8 (3)
C5B—C4B—H4B119.5C8D—S1D—C1D90.87 (18)
C3B—C4B—H4B119.5C8D—S1D—S1Bi137.93 (13)
C4B—C5B—C6B118.9 (4)C1D—S1D—S1Bi92.50 (13)
C4B—C5B—H5B120.5C8D—C7D—C6D112.5 (3)
C6B—C5B—H5B120.5C8D—C7D—H7D123.8
C1B—C6B—C5B119.3 (3)C6D—C7D—H7D123.8
C1B—C6B—C7B111.8 (3)C7D—C8D—C9D127.8 (3)
C5B—C6B—C7B128.9 (3)C7D—C8D—S1D113.3 (3)
C1B—S1B—C8B91.17 (17)C9D—C8D—S1D118.8 (3)
C8B—C7B—C6B112.6 (3)N1D—C9D—C8D115.6 (3)
C8B—C7B—H7B123.7N1D—C9D—C10D124.3 (3)
C6B—C7B—H7B123.7C8D—C9D—C10D120.1 (3)
C7B—C8B—C9B128.3 (3)C9D—C10D—H10J109.5
C7B—C8B—S1B112.5 (3)C9D—C10D—H10K109.5
C9B—C8B—S1B119.2 (3)H10J—C10D—H10K109.5
N1B—C9B—C8B114.7 (3)C9D—C10D—H10L109.5
N1B—C9B—C10B125.7 (3)H10J—C10D—H10L109.5
C8B—C9B—C10B119.7 (3)H10K—C10D—H10L109.5
C9B—C10B—H10D109.5C9D—N1D—N2D116.7 (3)
C9B—C10B—H10E109.5C11D—N2D—N1D119.1 (3)
H10D—C10B—H10E109.5C11D—N2D—H2ND123 (4)
C9B—C10B—H10F109.5N1D—N2D—H2ND117 (4)
H10D—C10B—H10F109.5N3D—C11D—N2D118.3 (3)
H10E—C10B—H10F109.5N3D—C11D—S2D123.5 (3)
C9B—N1B—N2B117.2 (3)N2D—C11D—S2D118.2 (3)
C11B—N2B—N1B117.9 (3)C11D—N3D—H3N7120 (3)
C11B—N2B—H2NB118 (3)C11D—N3D—H3N8116 (3)
N1B—N2B—H2NB125 (3)H3N7—N3D—H3N8124 (5)
N3B—C11B—N2B117.4 (3)C1S—O1S—H1S109.5
N3B—C11B—S2B122.8 (3)O1S—C1S—H1S1109.5
N2B—C11B—S2B119.8 (3)O1S—C1S—H1S2109.5
C11B—N3B—H3N3116 (3)H1S1—C1S—H1S2109.5
C11B—N3B—H3N4115 (3)O1S—C1S—H1S3109.5
H3N3—N3B—H3N4129 (4)H1S1—C1S—H1S3109.5
C2C—C1C—C6C121.8 (3)H1S2—C1S—H1S3109.5
C2C—C1C—S1C126.7 (3)C2S—O2S—H2S109.5
C6C—C1C—S1C111.5 (3)O2S—C2S—H2S1109.5
C3C—C2C—C1C117.9 (4)O2S—C2S—H2S2109.5
C3C—C2C—H2C121.1H2S1—C2S—H2S2109.5
C1C—C2C—H2C121.1O2S—C2S—H2S3109.5
C2C—C3C—C4C121.0 (4)H2S1—C2S—H2S3109.5
C2C—C3C—H3C119.5H2S2—C2S—H2S3109.5

Symmetry codes: (i) x, −y+3/2, z−1/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3A—H3N2···N1A0.843 (10)2.29 (4)2.641 (4)105 (3)
N3B—H3N3···N1B0.838 (10)2.21 (4)2.617 (4)110 (3)
N3C—H3N5···N1C0.842 (10)2.22 (5)2.543 (4)102 (4)
N3D—H3N7···N1D0.841 (10)2.29 (5)2.643 (4)105 (4)
N3A—H3N1···S2Bii0.839 (10)2.500 (14)3.325 (3)168 (4)
N3B—H3N4···S2Aiii0.839 (10)2.62 (2)3.367 (3)149 (4)
N2B—H2NB···S2Aiv0.839 (10)2.585 (13)3.412 (3)169 (4)
N3C—H3N6···S2Av0.840 (10)2.76 (4)3.352 (3)129 (4)
N3C—H3N6···N3Bvi0.840 (10)2.72 (3)3.468 (5)149 (5)
N2C—H2NC···S2Cvii0.842 (10)2.60 (2)3.392 (3)158 (4)
N3D—H3N8···S2Av0.840 (10)2.738 (15)3.563 (3)168 (4)
N3D—H3N7···O1S0.841 (10)2.26 (3)2.967 (6)142 (4)
O1S—H1S···S2Cvii0.842.643.471 (5)169
O2S—H2S···S2Dviii0.842.973.389 (6)113
C3A—H3A···S2Av0.952.973.762 (4)142
C10A—H10A···S2Bix0.982.913.613 (3)129
C2B—H2B···O1Sx0.952.363.282 (7)163
C2S—H2S1···N2Dviii0.982.743.266 (9)115
C10B—H10F···Cgxi0.982.913.594 (4)129

Symmetry codes: (ii) x+1, y, z; (iii) x−1, y, z; (iv) x−1, −y+3/2, z−1/2; (v) −x+1, y−1/2, −z+3/2; (vi) −x, y−1/2, −z+3/2; (vii) −x, −y+1, −z+1; (viii) −x+1, −y+1, −z+1; (ix) x+1, −y+3/2, z+1/2; (x) x, −y+3/2, z+1/2; (xi) −x, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2725).

References

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