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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1632–o1633.
Published online 2008 July 31. doi:  10.1107/S1600536808023556
PMCID: PMC2962238

3,3′-Bis(3,4,5-trimethoxy­benzo­yl)-1,1′-(o-phenyl­ene)dithio­urea ethanol solvate

Abstract

In the mol­ecule of the title compound, C28H30N4O8S2·C2H6O, the benzene ring is oriented at dihedral angles of 38.50 (6) and 5.68 (5)° with respect to the trimethoxy­phenyl rings, while the two trimethoxy­phenyl rings are oriented at a dihedral angle of 44.18 (5)°. Intra­molecular N—H(...)O and N—H(...)S hydrogen bonds result in the formation of non-planar six-, seven- and eight-membered rings. The twisting modes of the two side arms are different [C—N—C—O and C—N—C—N torsion angles = 0.1 (3) and 11.8 (3)°, respectively, in one arm, and 4.6 (3) and −11.5 (3)° in the other]. In the crystal structure, inter­molecular N—H(...)O and O—H(...)O hydrogen bonds link the mol­ecules.

Related literature

For a related structure, see: Thiam et al. (2008 [triangle]). For ring conformation puckering parameters, see: Cremer & Pople (1975 [triangle]).

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Object name is e-64-o1632-scheme1.jpg

Experimental

Crystal data

  • C28H30N4O8S2·C2H6O
  • M r = 660.75
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1632-efi1.jpg
  • a = 7.7619 (15) Å
  • b = 14.473 (3) Å
  • c = 15.810 (3) Å
  • α = 67.113 (10)°
  • β = 73.069 (9)°
  • γ = 78.210 (12)°
  • V = 1556.9 (5) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.23 mm−1
  • T = 113 (2) K
  • 0.14 × 0.12 × 0.10 mm

Data collection

  • Rigaku Saturn CCD area-detector diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 [triangle]) T min = 0.968, T max = 0.977
  • 18692 measured reflections
  • 6824 independent reflections
  • 5694 reflections with I > 2σ(I)
  • R int = 0.046

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.115
  • S = 1.07
  • 6824 reflections
  • 433 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.32 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2005 [triangle]); 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/S1600536808023556/hk2504sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023556/hk2504Isup2.hkl

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

Acknowledgments

The authors thank Guiyang College for financial support.

supplementary crystallographic information

Comment

In the molecule of the title compound (Fig. 1) the bond lengths and angles are within normal ranges. Rings A (C1-C6), B (C9-C14) and C (C17-C22) are, of course, planar, and the dihedral angles between them are A/B = 38.50 (6)°, A/C = 5.68 (5)° and B/C = 44.18 (5)°.

The intramolecular N-H···O and N-H···S hydrogen bonds (Table 1) result in the formation of non-planar six-, seven- and eight-membered rings: D (O1/N1/N3/C7/C8/H1), E (O2/N2/N4/C15/C16/H2), F (S1/N1/N2/C1/C2/C7/H2) and G (S1/O2/O9/N3/C7/H2/H3A/H9). Rings D and E adopt flattened-boat [[var phi] = 171.38 (2)°, θ = 109.10 (3)° (for ring D) and [var phi] = -20.28 (3)°, θ = 96.87 (3)° (for ring E)] conformations, while rings F and G adopt highly twisted conformations having total puckering amplitudes, QT, of 0.160 (3), 0.109 (3), 2.486 (4) and 2.064 (4) Å, respectively (Cremer & Pople, 1975). The two side arms are not twisted in the same way, as evidenced by the torsion angles: C7-N3-C8-O1 [0.1 (3)°], C8-N3-C7-N1 [11.8 (3)°] and C15-N4-C16-O2 [4.6 (3)°], C16-N4-C15-N2 [-11.5 (3)°], as in 1,2-bis(N'-benzoylthioureido)- benzene (Thiam et al., 2008).

In the crystal structure, intermolecular N-H···O hydrogen bonds link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental

For the preparation of the title compound, ammonium thiocyanate (30 mmol), 3,4,5-trimethoxylbenzoyl chloride (20 mmol), PEG-400 (0.2 mmol) and acetone (50 mL) were placed in a dried round-bottomed flask containing a magnetic stirrer bar and stirred at room temperature for 1 h, then benzene-1,2-diamine (9.5 mmol) was added, and the mixture was stirred for 2 h. The mixture was poured into water (20 ml). The resulting solid was filtered, washed with water, and then dried. Crystals suitable for X-ray analysis were obtained by the recrystallization of the solid residue from a mixture of N,N-dimethyl- formamide/ethanol (1:1) by slow evaporation at room temperature.

Refinement

H1, H2, H3A, H4A (for NH) and H9 (for OH) atoms were located in difference syntheses and refined isotropically [N-H = 0.84 (2)-0.90 (2) Å and Uiso(H) = 0.026 (6)-0.036 (7) Å2; O-H = 0.80 (3) Å and Uiso(H) = 0.043 Å2]. The remaining H atoms were positioned geometrically, with C-H = 0.95, 0.98 and 0.99 Å for aromatic, methyl and methylene H, respectively, and constrained to ride on their parent atoms with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

Crystal data

C28H30N4O8S2·C2H6O1Z = 2
Mr = 660.75F000 = 696
Triclinic, P1Dx = 1.409 Mg m3
Hall symbol: -P 1Melting point: 475 K
a = 7.7619 (15) ÅMo Kα radiation λ = 0.71070 Å
b = 14.473 (3) ÅCell parameters from 4542 reflections
c = 15.810 (3) Åθ = 2.4–27.2º
α = 67.113 (10)ºµ = 0.23 mm1
β = 73.069 (9)ºT = 113 (2) K
γ = 78.210 (12)ºBlock, colorless
V = 1556.9 (5) Å30.14 × 0.12 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer6824 independent reflections
Radiation source: rotating anode5694 reflections with I > 2σ(I)
Monochromator: confocalRint = 0.046
Detector resolution: 14.63 pixels mm-1θmax = 27.2º
T = 113(2) Kθmin = 2.5º
ω scansh = −9→9
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2005)k = −18→18
Tmin = 0.968, Tmax = 0.977l = −20→20
18692 measured reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.050  w = 1/[σ2(Fo2) + (0.0441P)2 + 0.4672P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.115(Δ/σ)max < 0.001
S = 1.07Δρmax = 0.26 e Å3
6824 reflectionsΔρmin = −0.32 e Å3
433 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0140 (12)
Secondary atom site location: difference Fourier map

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 > 2sigma(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
S10.47072 (7)0.74462 (4)0.51329 (3)0.02065 (14)
S20.93034 (8)0.44117 (4)0.34131 (4)0.02578 (15)
O11.02467 (19)0.81993 (11)0.48592 (9)0.0250 (3)
O20.6648 (2)0.51201 (10)0.60921 (10)0.0274 (4)
O31.2473 (2)0.92569 (11)0.70183 (10)0.0286 (4)
O41.0727 (2)0.82041 (11)0.87598 (10)0.0278 (4)
O50.7886 (2)0.72356 (11)0.90656 (10)0.0287 (4)
O60.7859 (2)0.27652 (10)0.93150 (10)0.0243 (3)
O70.7307 (2)0.09337 (10)0.94217 (9)0.0244 (3)
O80.6871 (2)0.06352 (10)0.79539 (9)0.0229 (3)
O90.5525 (2)0.62076 (12)0.74010 (11)0.0285 (4)
H90.568 (4)0.582 (2)0.7125 (19)0.043*
N10.8159 (2)0.76073 (12)0.41701 (11)0.0177 (4)
H10.923 (3)0.7772 (17)0.4133 (16)0.030 (7)*
N20.7346 (2)0.57673 (12)0.42050 (12)0.0200 (4)
H20.685 (3)0.5885 (17)0.4737 (17)0.028 (6)*
N30.7451 (2)0.76939 (12)0.56722 (12)0.0184 (4)
H3A0.673 (3)0.7516 (17)0.6201 (17)0.026 (6)*
N40.7865 (2)0.41196 (12)0.52015 (11)0.0198 (4)
H4A0.830 (3)0.3486 (19)0.5237 (17)0.036 (7)*
C10.7839 (3)0.75352 (14)0.33508 (13)0.0175 (4)
C20.7479 (3)0.66254 (14)0.33554 (13)0.0176 (4)
C30.7222 (3)0.65850 (15)0.25351 (14)0.0207 (4)
H30.69110.59810.25390.025*
C40.7419 (3)0.74278 (16)0.17098 (14)0.0238 (5)
H40.72720.73920.11480.029*
C50.7829 (3)0.83206 (16)0.17021 (14)0.0249 (5)
H50.79870.88900.11340.030*
C60.8006 (3)0.83775 (15)0.25285 (14)0.0213 (4)
H60.82420.89950.25320.026*
C70.6875 (3)0.75825 (13)0.49576 (13)0.0167 (4)
C80.9074 (3)0.79901 (14)0.56059 (14)0.0193 (4)
C90.9324 (3)0.80961 (14)0.64638 (14)0.0191 (4)
C101.0706 (3)0.86638 (14)0.63139 (14)0.0199 (4)
H101.13580.90010.56900.024*
C111.1123 (3)0.87340 (15)0.70806 (14)0.0207 (4)
C121.0173 (3)0.82339 (15)0.80012 (14)0.0217 (4)
C130.8750 (3)0.76923 (15)0.81379 (13)0.0215 (4)
C140.8326 (3)0.76151 (15)0.73745 (14)0.0219 (4)
H140.73700.72400.74710.026*
C150.8105 (3)0.48263 (14)0.42749 (14)0.0189 (4)
C160.7225 (3)0.42760 (15)0.60517 (14)0.0197 (4)
C170.7314 (3)0.33652 (14)0.69148 (13)0.0180 (4)
C180.7536 (3)0.35253 (15)0.76900 (14)0.0200 (4)
H180.76620.41820.76470.024*
C190.7570 (3)0.27097 (15)0.85280 (13)0.0193 (4)
C200.7301 (3)0.17510 (14)0.86015 (13)0.0187 (4)
C210.7114 (3)0.16009 (14)0.78097 (14)0.0187 (4)
C220.7134 (3)0.24057 (14)0.69593 (13)0.0172 (4)
H220.70260.23040.64190.021*
C231.3530 (3)0.97237 (17)0.60921 (16)0.0301 (5)
H23A1.41180.92090.58120.045*
H23B1.44551.00690.61270.045*
H23C1.27441.02140.57010.045*
C240.9843 (3)0.89960 (16)0.91201 (15)0.0274 (5)
H24A1.01100.96510.86280.041*
H24B1.02850.89180.96670.041*
H24C0.85320.89580.93110.041*
C250.6375 (3)0.67215 (18)0.92291 (16)0.0349 (6)
H25A0.54740.71920.89030.052*
H25B0.58340.64550.99090.052*
H25C0.67770.61640.89880.052*
C260.8306 (3)0.37088 (16)0.92470 (15)0.0277 (5)
H26A0.93370.39260.87090.042*
H26B0.86240.36290.98290.042*
H26C0.72620.42170.91560.042*
C270.5853 (3)0.09950 (17)1.02149 (16)0.0348 (6)
H27A0.62190.13371.05520.052*
H27B0.55730.03141.06430.052*
H27C0.47770.13760.99890.052*
C280.6740 (3)0.04397 (15)0.71577 (14)0.0249 (5)
H28A0.56840.08490.69290.037*
H28B0.6608−0.02760.73430.037*
H28C0.78390.06130.66540.037*
C290.3609 (3)0.63770 (18)0.77554 (16)0.0312 (5)
H29A0.29870.65090.72490.037*
H29B0.33430.69830.79370.037*
C300.2880 (4)0.5489 (2)0.85986 (17)0.0428 (7)
H30A0.31030.48930.84160.064*
H30B0.15750.56390.88240.064*
H30C0.34890.53580.91030.064*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0181 (3)0.0241 (3)0.0211 (3)−0.00133 (19)−0.0054 (2)−0.0093 (2)
S20.0320 (3)0.0201 (3)0.0198 (3)0.0011 (2)−0.0011 (2)−0.0068 (2)
O10.0240 (8)0.0343 (8)0.0179 (7)−0.0081 (6)−0.0015 (6)−0.0103 (6)
O20.0436 (10)0.0171 (7)0.0200 (8)0.0031 (6)−0.0090 (7)−0.0070 (6)
O30.0308 (9)0.0363 (9)0.0256 (8)−0.0101 (7)−0.0086 (7)−0.0137 (7)
O40.0350 (9)0.0317 (8)0.0237 (8)0.0064 (6)−0.0154 (7)−0.0160 (7)
O50.0367 (9)0.0332 (8)0.0156 (7)−0.0084 (7)−0.0045 (6)−0.0069 (6)
O60.0353 (9)0.0211 (7)0.0203 (7)−0.0044 (6)−0.0106 (6)−0.0076 (6)
O70.0329 (9)0.0187 (7)0.0160 (7)0.0021 (6)−0.0059 (6)−0.0024 (6)
O80.0356 (9)0.0149 (7)0.0202 (7)−0.0050 (6)−0.0100 (6)−0.0046 (6)
O90.0278 (9)0.0318 (9)0.0286 (9)−0.0028 (7)−0.0046 (7)−0.0149 (7)
N10.0187 (9)0.0202 (8)0.0159 (8)−0.0019 (6)−0.0051 (7)−0.0073 (7)
N20.0280 (10)0.0165 (8)0.0142 (8)−0.0005 (7)−0.0056 (7)−0.0045 (7)
N30.0199 (9)0.0227 (9)0.0134 (8)−0.0030 (7)−0.0032 (7)−0.0074 (7)
N40.0268 (10)0.0137 (8)0.0165 (8)−0.0013 (7)−0.0036 (7)−0.0041 (7)
C10.0152 (10)0.0219 (10)0.0155 (9)0.0005 (7)−0.0032 (7)−0.0084 (8)
C20.0171 (10)0.0183 (9)0.0158 (9)0.0013 (7)−0.0035 (8)−0.0061 (8)
C30.0218 (11)0.0214 (10)0.0202 (10)0.0017 (8)−0.0066 (8)−0.0094 (8)
C40.0252 (11)0.0293 (11)0.0184 (10)0.0045 (8)−0.0084 (8)−0.0112 (9)
C50.0285 (12)0.0248 (11)0.0155 (10)0.0012 (8)−0.0048 (9)−0.0031 (8)
C60.0229 (11)0.0174 (10)0.0197 (10)−0.0010 (8)−0.0031 (8)−0.0043 (8)
C70.0219 (10)0.0131 (9)0.0151 (9)0.0000 (7)−0.0069 (8)−0.0039 (7)
C80.0206 (10)0.0176 (9)0.0205 (10)−0.0003 (7)−0.0067 (8)−0.0071 (8)
C90.0209 (10)0.0194 (10)0.0195 (10)0.0019 (8)−0.0069 (8)−0.0098 (8)
C100.0201 (10)0.0198 (10)0.0190 (10)0.0009 (8)−0.0057 (8)−0.0066 (8)
C110.0210 (11)0.0215 (10)0.0234 (10)0.0007 (8)−0.0072 (8)−0.0117 (8)
C120.0263 (11)0.0229 (10)0.0208 (10)0.0051 (8)−0.0121 (9)−0.0119 (8)
C130.0254 (11)0.0217 (10)0.0151 (10)0.0019 (8)−0.0055 (8)−0.0056 (8)
C140.0241 (11)0.0213 (10)0.0212 (10)−0.0013 (8)−0.0063 (8)−0.0083 (8)
C150.0197 (10)0.0178 (9)0.0201 (10)−0.0032 (7)−0.0058 (8)−0.0061 (8)
C160.0222 (10)0.0197 (10)0.0180 (10)−0.0037 (8)−0.0055 (8)−0.0063 (8)
C170.0176 (10)0.0189 (10)0.0158 (9)0.0005 (7)−0.0034 (8)−0.0057 (8)
C180.0217 (10)0.0182 (10)0.0211 (10)−0.0023 (7)−0.0051 (8)−0.0077 (8)
C190.0195 (10)0.0240 (10)0.0150 (9)−0.0009 (8)−0.0047 (8)−0.0077 (8)
C200.0199 (10)0.0173 (9)0.0159 (9)−0.0013 (7)−0.0047 (8)−0.0027 (8)
C210.0176 (10)0.0161 (9)0.0233 (10)−0.0024 (7)−0.0054 (8)−0.0071 (8)
C220.0175 (10)0.0187 (9)0.0149 (9)−0.0020 (7)−0.0037 (7)−0.0051 (8)
C230.0306 (13)0.0312 (12)0.0327 (12)−0.0105 (9)−0.0052 (10)−0.0137 (10)
C240.0357 (13)0.0284 (11)0.0226 (11)−0.0013 (9)−0.0092 (9)−0.0129 (9)
C250.0463 (15)0.0343 (13)0.0222 (11)−0.0170 (11)0.0012 (10)−0.0083 (10)
C260.0365 (13)0.0264 (11)0.0263 (11)−0.0053 (9)−0.0096 (10)−0.0129 (9)
C270.0348 (13)0.0300 (12)0.0250 (12)−0.0045 (10)0.0006 (10)0.0008 (10)
C280.0355 (13)0.0191 (10)0.0235 (11)−0.0022 (8)−0.0110 (9)−0.0086 (9)
C290.0277 (12)0.0373 (13)0.0277 (12)−0.0028 (9)−0.0076 (10)−0.0100 (10)
C300.0557 (17)0.0482 (16)0.0263 (13)−0.0224 (13)0.0021 (12)−0.0150 (12)

Geometric parameters (Å, °)

S1—C71.664 (2)C9—C101.393 (3)
S2—C151.659 (2)C9—C141.396 (3)
O1—C81.234 (2)C10—C111.386 (3)
O2—C161.232 (2)C10—H100.9500
O3—C111.373 (2)C11—C121.400 (3)
O3—C231.425 (3)C12—C131.402 (3)
O4—C121.370 (2)C13—C141.389 (3)
O4—C241.438 (2)C14—H140.9500
O5—C131.375 (2)C16—C171.491 (3)
O5—C251.423 (3)C17—C181.395 (3)
O6—C191.361 (2)C17—C221.397 (3)
O6—C261.433 (2)C18—C191.393 (3)
O7—C201.374 (2)C18—H180.9500
O7—C271.441 (3)C19—C201.400 (3)
O8—C211.370 (2)C20—C211.402 (3)
O8—C281.428 (2)C21—C221.393 (3)
O9—C291.434 (3)C22—H220.9500
O9—H90.80 (3)C23—H23A0.9800
N1—C71.342 (2)C23—H23B0.9800
N1—C11.433 (3)C23—H23C0.9800
N1—H10.89 (2)C24—H24A0.9800
N2—C151.344 (3)C24—H24B0.9800
N2—C21.425 (2)C24—H24C0.9800
N2—H20.88 (2)C25—H25A0.9800
N3—C81.375 (3)C25—H25B0.9800
N3—C71.403 (3)C25—H25C0.9800
N3—H3A0.84 (2)C26—H26A0.9800
N4—C161.381 (3)C26—H26B0.9800
N4—C151.407 (2)C26—H26C0.9800
N4—H4A0.90 (2)C27—H27A0.9800
C1—C61.388 (3)C27—H27B0.9800
C1—C21.398 (3)C27—H27C0.9800
C2—C31.393 (3)C28—H28A0.9800
C3—C41.391 (3)C28—H28B0.9800
C3—H30.9500C28—H28C0.9800
C4—C51.387 (3)C29—C301.508 (3)
C4—H40.9500C29—H29A0.9900
C5—C61.388 (3)C29—H29B0.9900
C5—H50.9500C30—H30A0.9800
C6—H60.9500C30—H30B0.9800
C8—C91.493 (3)C30—H30C0.9800
C11—O3—C23116.05 (16)C18—C17—C22121.48 (17)
C12—O4—C24114.05 (15)C18—C17—C16116.36 (18)
C13—O5—C25116.56 (17)C22—C17—C16122.13 (18)
C19—O6—C26117.41 (16)C19—C18—C17119.18 (18)
C20—O7—C27114.85 (15)C19—C18—H18120.4
C21—O8—C28117.05 (15)C17—C18—H18120.4
C29—O9—H9107.2 (19)O6—C19—C18124.44 (18)
C7—N1—C1124.35 (17)O6—C19—C20115.37 (17)
C7—N1—H1116.3 (15)C18—C19—C20120.19 (18)
C1—N1—H1118.6 (15)O7—C20—C19121.59 (18)
C15—N2—C2125.79 (17)O7—C20—C21118.60 (17)
C15—N2—H2117.3 (15)C19—C20—C21119.73 (17)
C2—N2—H2116.3 (15)O8—C21—C22124.37 (18)
C8—N3—C7127.62 (17)O8—C21—C20115.14 (17)
C8—N3—H3A118.5 (16)C22—C21—C20120.47 (18)
C7—N3—H3A113.8 (16)C21—C22—C17118.83 (18)
C16—N4—C15129.46 (17)C21—C22—H22120.6
C16—N4—H4A116.0 (15)C17—C22—H22120.6
C15—N4—H4A114.3 (15)O3—C23—H23A109.5
C6—C1—C2120.34 (18)O3—C23—H23B109.5
C6—C1—N1118.33 (18)H23A—C23—H23B109.5
C2—C1—N1121.21 (17)O3—C23—H23C109.5
C3—C2—C1119.20 (18)H23A—C23—H23C109.5
C3—C2—N2121.58 (18)H23B—C23—H23C109.5
C1—C2—N2119.21 (17)O4—C24—H24A109.5
C4—C3—C2120.1 (2)O4—C24—H24B109.5
C4—C3—H3120.0H24A—C24—H24B109.5
C2—C3—H3120.0O4—C24—H24C109.5
C5—C4—C3120.44 (19)H24A—C24—H24C109.5
C5—C4—H4119.8H24B—C24—H24C109.5
C3—C4—H4119.8O5—C25—H25A109.5
C4—C5—C6119.65 (19)O5—C25—H25B109.5
C4—C5—H5120.2H25A—C25—H25B109.5
C6—C5—H5120.2O5—C25—H25C109.5
C5—C6—C1120.21 (19)H25A—C25—H25C109.5
C5—C6—H6119.9H25B—C25—H25C109.5
C1—C6—H6119.9O6—C26—H26A109.5
N1—C7—N3115.67 (17)O6—C26—H26B109.5
N1—C7—S1125.33 (15)H26A—C26—H26B109.5
N3—C7—S1118.99 (14)O6—C26—H26C109.5
O1—C8—N3121.57 (18)H26A—C26—H26C109.5
O1—C8—C9121.22 (18)H26B—C26—H26C109.5
N3—C8—C9117.16 (17)O7—C27—H27A109.5
C10—C9—C14120.91 (19)O7—C27—H27B109.5
C10—C9—C8115.91 (17)H27A—C27—H27B109.5
C14—C9—C8123.07 (18)O7—C27—H27C109.5
C11—C10—C9119.59 (18)H27A—C27—H27C109.5
C11—C10—H10120.2H27B—C27—H27C109.5
C9—C10—H10120.2O8—C28—H28A109.5
O3—C11—C10124.62 (18)O8—C28—H28B109.5
O3—C11—C12114.95 (18)H28A—C28—H28B109.5
C10—C11—C12120.41 (19)O8—C28—H28C109.5
O4—C12—C11120.25 (19)H28A—C28—H28C109.5
O4—C12—C13120.29 (18)H28B—C28—H28C109.5
C11—C12—C13119.24 (18)O9—C29—C30112.1 (2)
O5—C13—C14124.23 (19)O9—C29—H29A109.2
O5—C13—C12115.03 (18)C30—C29—H29A109.2
C14—C13—C12120.71 (18)O9—C29—H29B109.2
C13—C14—C9119.08 (19)C30—C29—H29B109.2
C13—C14—H14120.5H29A—C29—H29B107.9
C9—C14—H14120.5C29—C30—H30A109.5
N2—C15—N4114.99 (17)C29—C30—H30B109.5
N2—C15—S2128.09 (15)H30A—C30—H30B109.5
N4—C15—S2116.90 (14)C29—C30—H30C109.5
O2—C16—N4121.94 (18)H30A—C30—H30C109.5
O2—C16—C17122.15 (18)H30B—C30—H30C109.5
N4—C16—C17115.90 (17)
C7—N1—C1—C6112.1 (2)C11—C12—C13—O5−179.33 (17)
C7—N1—C1—C2−71.9 (2)O4—C12—C13—C14−171.96 (17)
C6—C1—C2—C3−2.4 (3)C11—C12—C13—C142.6 (3)
N1—C1—C2—C3−178.42 (17)O5—C13—C14—C9−178.68 (18)
C6—C1—C2—N2178.93 (17)C12—C13—C14—C9−0.8 (3)
N1—C1—C2—N22.9 (3)C10—C9—C14—C13−1.2 (3)
C15—N2—C2—C346.2 (3)C8—C9—C14—C13174.92 (18)
C15—N2—C2—C1−135.2 (2)C2—N2—C15—N4176.38 (18)
C1—C2—C3—C43.5 (3)C2—N2—C15—S2−2.4 (3)
N2—C2—C3—C4−177.94 (18)C16—N4—C15—N2−11.5 (3)
C2—C3—C4—C5−1.6 (3)C16—N4—C15—S2167.45 (17)
C3—C4—C5—C6−1.3 (3)C15—N4—C16—O24.6 (3)
C4—C5—C6—C12.3 (3)C15—N4—C16—C17−174.03 (19)
C2—C1—C6—C5−0.5 (3)O2—C16—C17—C18−28.7 (3)
N1—C1—C6—C5175.64 (18)N4—C16—C17—C18149.99 (18)
C1—N1—C7—N3−178.21 (16)O2—C16—C17—C22149.5 (2)
C1—N1—C7—S11.0 (3)N4—C16—C17—C22−31.8 (3)
C8—N3—C7—N111.8 (3)C22—C17—C18—C19−0.3 (3)
C8—N3—C7—S1−167.47 (15)C16—C17—C18—C19177.93 (18)
C7—N3—C8—O10.1 (3)C26—O6—C19—C18−5.4 (3)
C7—N3—C8—C9177.21 (17)C26—O6—C19—C20174.43 (17)
O1—C8—C9—C1015.1 (3)C17—C18—C19—O6176.90 (17)
N3—C8—C9—C10−162.03 (17)C17—C18—C19—C20−2.9 (3)
O1—C8—C9—C14−161.21 (19)C27—O7—C20—C1965.1 (3)
N3—C8—C9—C1421.6 (3)C27—O7—C20—C21−118.3 (2)
C14—C9—C10—C111.4 (3)O6—C19—C20—O70.9 (3)
C8—C9—C10—C11−174.97 (17)C18—C19—C20—O7−179.27 (17)
C23—O3—C11—C10−2.1 (3)O6—C19—C20—C21−175.70 (17)
C23—O3—C11—C12176.46 (17)C18—C19—C20—C214.1 (3)
C9—C10—C11—O3178.88 (18)C28—O8—C21—C224.0 (3)
C9—C10—C11—C120.4 (3)C28—O8—C21—C20−177.79 (17)
C24—O4—C12—C1193.5 (2)O7—C20—C21—O82.8 (3)
C24—O4—C12—C13−92.0 (2)C19—C20—C21—O8179.51 (17)
O3—C11—C12—O4−6.4 (3)O7—C20—C21—C22−178.87 (17)
C10—C11—C12—O4172.17 (17)C19—C20—C21—C22−2.2 (3)
O3—C11—C12—C13178.98 (17)O8—C21—C22—C17177.19 (17)
C10—C11—C12—C13−2.4 (3)C20—C21—C22—C17−1.0 (3)
C25—O5—C13—C14−5.1 (3)C18—C17—C22—C212.2 (3)
C25—O5—C13—C12176.94 (18)C16—C17—C22—C21−175.89 (18)
O4—C12—C13—O56.1 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N4—H4A···O1i0.90 (2)2.51 (2)3.403 (2)173 (2)
N2—H2···S10.88 (2)2.69 (2)3.3527 (19)133.0 (18)
N2—H2···O20.88 (2)1.97 (2)2.677 (2)136 (2)
N1—H1···O10.89 (2)1.90 (2)2.621 (2)137 (2)
N3—H3A···O90.84 (2)2.23 (2)2.949 (2)145 (2)
O9—H9···O20.80 (3)2.13 (3)2.905 (2)163 (3)

Symmetry codes: (i) −x+2, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2504).

References

  • Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc.97, 1354–1358.
  • Rigaku/MSC. (2005). CrystalClear and CrystalStructure Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Thiam, E. I., Diop, M., Gaye, M., Sall, A. S. & Barry, A. H. (2008). Acta Cryst. E64, o776. [PMC free article] [PubMed]

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