PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2305.
Published online 2008 November 13. doi:  10.1107/S1600536808035964
PMCID: PMC2959801

4-(4-Chloro­phen­yl)-1-(2-hydr­oxy-2,2-di­phenyl­acet­yl)thio­semicarbazide

Abstract

The asymmetric unit of the title compound, C21H18ClN3O2S, contains two mol­ecules in which the bond lengths and angles are almost identical. Intra­molecular N—H(...)S hydrogen bonds result in the formation of two five-membered rings. In the crystal structure, inter­molecular N—H(...)O hydrogen bonds link the mol­ecules into centrosymmetric dimers; these dimers are linked via inter­molecular O—H(...)S hydrogen bonds, leading to infinite corrugated layers parallel to the bc plane through R 2 2(16) ring motifs.

Related literature

For a related structure, see: Ergenç et al. (1992 [triangle]). For general background, see: Jalilian et al. (2000 [triangle]); John (1998 [triangle]); Kucukguzel et al. (2006 [triangle]); Shen et al. (1998 [triangle]); Singh et al. (2005 [triangle]). For ring motifs, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2305-scheme1.jpg

Experimental

Crystal data

  • C21H18ClN3O2S
  • M r = 411.89
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2305-efi3.jpg
  • a = 14.1039 (19) Å
  • b = 18.1566 (19) Å
  • c = 16.9108 (19) Å
  • β = 114.509 (10)°
  • V = 3940.3 (9) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.32 mm−1
  • T = 173 (2) K
  • 0.9 × 0.4 × 0.4 mm

Data collection

  • Bruker P4 diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.837, T max = 0.879
  • 20863 measured reflections
  • 9027 independent reflections
  • 6867 reflections with I > 2σ(I)
  • R int = 0.029
  • 2 standard reflections every 98 reflections intensity decay: none

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.102
  • S = 1.02
  • 9027 reflections
  • 532 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.91 e Å−3
  • Δρmin = −0.82 e Å−3

Data collection: XSCANS (Bruker, 1996 [triangle]); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536808035964/hk2559sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035964/hk2559Isup2.hkl

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

Acknowledgments

The Deanship of Scientific Research at the Hashemite University and Al al-Bayt University are thanked for financial support. We also thank the DFG (Bonn, Germany) for financial support.

supplementary crystallographic information

Comment

Thiosemicarbazides have received special interest for their potential biological activities (Kucukguzel et al., 2006; Singh et al., 2005). They have also received considerable attention because of the possibility of their use as intermediates in the synthesis of many biologically active heterocyclic compounds such as 1,2,4-triazole derivatives (Ergenç et al., 1992), 1,3,4-thiadiazoles (Jalilian et al., 2000) and many others. As ligands, thiosemicarbazides are useful bidentate ligands (S- and N- donors) for transition metal ions and their complexes possess many biological activities (Shen et al., 1998). The title compound was synthesized as an intermediate for biologically active 1,2,4-triazole derivative (Ergenç et al., 1992). We report herein its crystal structure.

The asymmetric unit of the title compound contains two independent thiosemicarbazide molecules (Fig 1), where the bond lengths and angles are almost identical (Table 1). In both molecules, the linking C-N-N-C-N units are delocalized and flattened. The C-S and C-O bonds both show the double bond character, while the C-N and N-N bonds in the linking units imply significant electron delocalization. As a result of conjugation, O2-C14 [1.241 (2) Å] and O5-C35 [1.242 (2) Å] bonds are longer than the normal value of 1.20 Å (John, 1998), while N1-C14 [1.323 (2) Å] and N4-C35 [1.327 (2) Å] bonds are in accordance with the C-N double bond length (1.32 A°; John, 1998) and shorter than the C-N single bond length (1.475 A°; John, 1998). The sum of the bond angles around N1, N2, N3, C14, C15 and N4, N5, N6, C35, C36 atoms are about 360°, which implies sp2 hybridization for these atoms. The thiourea group is approximately planar. The intramolecular N-H···S hydrogen bonds (Table 2) result in the formation of two five-membered rings (S1/N1/N2/C15/H1N) and (S2/N4/N5/C36/H4N).

In the crystal structure, intermolecular N-H···O hydrogen bonds (Table 2) link the molecules into centrosymmetric dimers (Fig. 2), in which they are also linked to the other dimers via intermolecular O-H···S hydrogen bonds (Table 2) leading to infinite corrugated layers parallel to the bc plane through R22(16) ring motifs (Bernstein et al., 1995).

Experimental

The title compound was synthesized according to the literature method (Ergenç et al., 1992) by the reaction of equimolar amounts of 2-hydroxy-2,2-diphenyl- acetohydrazide, (1), and 1-chloro-4-isothiocyanatobenzene, (2), (Fig. 3). Crystals suitable for X-ray analysis were obtained by recrystallization from a methanol solution at room temperature.

Refinement

H1N, H2N, H3N, H4N, H5N and H6N atoms (for NH) were located in difference syntheses and refined isotropically [N-H = 0.81 (2)-0.90 (2) Å and Uiso(H) = 0.032 (5)-0.046 (7) Å2]. The remaining H atoms were positioned geometrically, with O-H = 0.84 Å (for OH) and C-H = 0.95 Å for aromatic H, respectively, and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C,O).

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. Hydrogen bonds are shown as dashed lines [symmetry codes: (i) x, 3/2 - y, z + 1/2; (ii) x, y, z + 1]. H atoms not involved in hydrogen bonding are omitted for clarity.
Fig. 3.
A schematic representation of the reaction that afforded the title compound.

Crystal data

C21H18ClN3O2SF000 = 1712
Mr = 411.89Dx = 1.389 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 51 reflections
a = 14.1039 (19) Åθ = 4.9–12.6º
b = 18.1566 (19) ŵ = 0.32 mm1
c = 16.9108 (19) ÅT = 173 (2) K
β = 114.509 (10)ºPrism, colorless
V = 3940.3 (9) Å30.9 × 0.4 × 0.4 mm
Z = 8

Data collection

Bruker P4 diffractometerRint = 0.029
Radiation source: fine-focus sealed tubeθmax = 27.5º
Monochromator: graphiteθmin = 2.2º
T = 173(2) Kh = −18→1
ω scansk = −23→23
Absorption correction: multi-scan(SADABS; Bruker, 2005)l = −20→21
Tmin = 0.837, Tmax = 0.8792 standard reflections
20863 measured reflections every 98 reflections
9027 independent reflections intensity decay: none
6867 reflections with I > 2σ(I)

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)] = 0.041  w = 1/[σ2(Fo2) + (0.0394P)2 + 1.5051P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.102(Δ/σ)max = 0.001
S = 1.02Δρmax = 0.91 e Å3
9027 reflectionsΔρmin = −0.82 e Å3
532 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0023 (2)
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 > 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
Cl1−0.35372 (4)0.47876 (3)0.91532 (4)0.04719 (14)
S10.10518 (4)0.53220 (3)0.84004 (3)0.03220 (11)
O10.40810 (11)0.59866 (7)0.86727 (8)0.0351 (3)
H1O0.41360.59830.81970.053*
O20.34635 (10)0.74781 (7)0.97416 (9)0.0372 (3)
N10.26430 (12)0.64596 (9)0.90301 (10)0.0316 (3)
H1N0.2627 (16)0.6047 (12)0.8741 (14)0.041 (6)*
N20.18196 (12)0.65529 (9)0.92635 (11)0.0327 (4)
H2N0.1839 (18)0.6904 (13)0.9562 (15)0.046 (7)*
N30.03119 (11)0.62184 (8)0.93040 (10)0.0280 (3)
H3N0.0423 (15)0.6629 (11)0.9608 (13)0.032 (5)*
C10.53250 (13)0.66591 (9)0.98982 (11)0.0265 (4)
C20.59828 (14)0.72619 (10)1.02190 (12)0.0322 (4)
H20.58200.77140.99080.039*
C30.68734 (15)0.72099 (12)1.09875 (13)0.0384 (4)
H30.73140.76271.12020.046*
C40.71225 (16)0.65547 (12)1.14417 (13)0.0428 (5)
H4A0.77420.65161.19610.051*
C50.64697 (17)0.59559 (12)1.11394 (14)0.0436 (5)
H50.66350.55071.14570.052*
C60.55727 (15)0.60058 (10)1.03742 (13)0.0349 (4)
H60.51240.55921.01730.042*
C70.43300 (14)0.67069 (9)0.90531 (11)0.0281 (4)
C80.44508 (14)0.72594 (10)0.84178 (11)0.0305 (4)
C90.38732 (17)0.79023 (13)0.81501 (14)0.0450 (5)
H90.33580.80150.83560.054*
C100.4044 (2)0.83823 (15)0.75830 (17)0.0616 (7)
H100.36510.88240.74090.074*
C110.47860 (19)0.82192 (15)0.72685 (15)0.0557 (6)
H110.48970.85460.68760.067*
C120.53596 (16)0.75824 (13)0.75273 (13)0.0441 (5)
H120.58660.74690.73110.053*
C130.52029 (15)0.71046 (11)0.81031 (12)0.0355 (4)
H130.56100.66690.82850.043*
C140.34396 (13)0.69218 (10)0.93070 (11)0.0277 (4)
C150.10457 (13)0.60501 (9)0.90104 (11)0.0263 (4)
C16−0.06058 (13)0.58394 (9)0.92138 (11)0.0263 (4)
C17−0.08058 (14)0.50973 (10)0.90017 (11)0.0284 (4)
H17−0.03260.48090.88720.034*
C18−0.17141 (14)0.47832 (10)0.89816 (11)0.0305 (4)
H18−0.18580.42790.88310.037*
C19−0.24083 (13)0.51957 (11)0.91782 (12)0.0317 (4)
C20−0.22088 (15)0.59270 (11)0.94035 (14)0.0413 (5)
H20−0.26800.62090.95510.050*
C21−0.13118 (15)0.62458 (11)0.94123 (14)0.0391 (5)
H21−0.11780.67520.95570.047*
Cl20.85383 (5)1.00209 (4)0.11087 (5)0.06182 (19)
S20.40487 (4)0.95519 (3)0.18449 (3)0.03181 (11)
O40.09276 (10)0.90499 (7)0.15471 (8)0.0336 (3)
H4O0.08160.90660.19980.050*
O50.13097 (10)0.75772 (7)0.03205 (8)0.0342 (3)
N40.22880 (12)0.85044 (9)0.11506 (11)0.0325 (3)
H4N0.2363 (17)0.8894 (12)0.1476 (14)0.045 (6)*
N50.31033 (12)0.83735 (9)0.09191 (11)0.0362 (4)
H5N0.2991 (17)0.8017 (13)0.0518 (14)0.046 (6)*
N60.45659 (12)0.86864 (9)0.07879 (11)0.0350 (4)
H6N0.4369 (17)0.8333 (12)0.0391 (14)0.043 (6)*
C22−0.04212 (14)0.84829 (9)0.02956 (11)0.0277 (4)
C23−0.04205 (16)0.90432 (10)−0.02701 (12)0.0353 (4)
H230.01920.9327−0.01410.042*
C24−0.13058 (17)0.91890 (11)−0.10186 (13)0.0418 (5)
H24−0.12980.9574−0.13960.050*
C25−0.22013 (16)0.87771 (11)−0.12200 (13)0.0406 (5)
H25−0.28070.8877−0.17340.049*
C26−0.22073 (16)0.82195 (11)−0.06669 (13)0.0391 (4)
H26−0.28190.7933−0.08030.047*
C27−0.13221 (14)0.80740 (10)0.00893 (12)0.0319 (4)
H27−0.13360.76910.04670.038*
C280.05769 (14)0.83534 (9)0.11184 (11)0.0272 (4)
C290.04543 (14)0.77964 (10)0.17447 (11)0.0306 (4)
C300.10095 (18)0.71399 (13)0.19657 (15)0.0487 (5)
H300.14750.70190.17090.058*
C310.0892 (2)0.66601 (15)0.25556 (18)0.0653 (7)
H310.12750.62130.27000.078*
C320.0225 (2)0.68284 (15)0.29325 (15)0.0581 (7)
H320.01460.64970.33360.070*
C33−0.03331 (17)0.74784 (13)0.27265 (13)0.0466 (5)
H33−0.07920.75960.29900.056*
C34−0.02215 (15)0.79620 (11)0.21312 (12)0.0364 (4)
H34−0.06090.84080.19880.044*
C350.14256 (14)0.81022 (10)0.08231 (11)0.0285 (4)
C360.39154 (14)0.88456 (10)0.11629 (11)0.0293 (4)
C370.55058 (14)0.90486 (10)0.08987 (11)0.0290 (4)
C380.62840 (16)0.92071 (13)0.17052 (13)0.0420 (5)
H380.61830.91070.22160.050*
C390.72165 (16)0.95127 (13)0.17680 (14)0.0473 (5)
H390.77540.96230.23220.057*
C400.73569 (15)0.96547 (11)0.10254 (13)0.0366 (4)
C410.65866 (14)0.95032 (10)0.02156 (12)0.0322 (4)
H410.66910.9603−0.02940.039*
C420.56583 (14)0.92029 (10)0.01565 (11)0.0298 (4)
H420.51190.9101−0.03990.036*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0334 (3)0.0594 (3)0.0571 (3)−0.0161 (2)0.0271 (2)−0.0117 (3)
S10.0354 (2)0.0322 (2)0.0347 (2)−0.00651 (19)0.0203 (2)−0.00557 (18)
O10.0414 (8)0.0347 (7)0.0386 (7)−0.0121 (6)0.0261 (6)−0.0140 (6)
O20.0322 (7)0.0400 (7)0.0472 (8)−0.0083 (6)0.0245 (6)−0.0162 (6)
N10.0269 (8)0.0357 (9)0.0384 (8)−0.0060 (7)0.0196 (7)−0.0086 (7)
N20.0273 (8)0.0342 (9)0.0427 (9)−0.0073 (7)0.0206 (7)−0.0112 (7)
N30.0254 (8)0.0269 (8)0.0341 (8)−0.0040 (6)0.0149 (6)−0.0040 (6)
C10.0246 (8)0.0295 (9)0.0313 (9)−0.0011 (7)0.0174 (7)−0.0044 (7)
C20.0311 (10)0.0328 (9)0.0347 (9)−0.0040 (8)0.0158 (8)−0.0008 (8)
C30.0307 (10)0.0471 (12)0.0375 (10)−0.0097 (9)0.0143 (9)−0.0054 (9)
C40.0317 (10)0.0582 (13)0.0359 (10)0.0033 (10)0.0113 (9)0.0056 (9)
C50.0469 (12)0.0416 (11)0.0457 (12)0.0109 (10)0.0228 (10)0.0114 (9)
C60.0383 (11)0.0307 (9)0.0421 (10)−0.0011 (8)0.0232 (9)−0.0011 (8)
C70.0285 (9)0.0286 (9)0.0319 (9)−0.0054 (7)0.0173 (8)−0.0073 (7)
C80.0263 (9)0.0387 (10)0.0259 (8)−0.0073 (8)0.0102 (7)−0.0034 (7)
C90.0371 (11)0.0558 (13)0.0453 (12)0.0071 (10)0.0204 (10)0.0132 (10)
C100.0548 (15)0.0659 (16)0.0648 (16)0.0168 (13)0.0255 (13)0.0318 (13)
C110.0503 (14)0.0730 (17)0.0456 (13)−0.0039 (12)0.0216 (11)0.0225 (12)
C120.0372 (11)0.0629 (14)0.0365 (10)−0.0121 (10)0.0197 (9)−0.0011 (10)
C130.0334 (10)0.0429 (11)0.0352 (10)−0.0065 (9)0.0193 (8)−0.0045 (8)
C140.0246 (9)0.0323 (9)0.0285 (9)−0.0037 (7)0.0133 (7)−0.0026 (7)
C150.0245 (8)0.0294 (9)0.0245 (8)−0.0020 (7)0.0098 (7)0.0023 (7)
C160.0234 (8)0.0302 (9)0.0257 (8)−0.0016 (7)0.0107 (7)0.0027 (7)
C170.0249 (8)0.0298 (9)0.0310 (9)−0.0018 (7)0.0121 (7)−0.0002 (7)
C180.0281 (9)0.0328 (9)0.0297 (9)−0.0061 (7)0.0110 (7)−0.0015 (7)
C190.0235 (9)0.0410 (10)0.0316 (9)−0.0059 (8)0.0124 (7)0.0008 (8)
C200.0324 (10)0.0395 (11)0.0607 (13)0.0004 (9)0.0279 (10)−0.0055 (10)
C210.0349 (10)0.0312 (10)0.0577 (13)−0.0028 (8)0.0256 (10)−0.0059 (9)
Cl20.0482 (3)0.0682 (4)0.0875 (4)−0.0305 (3)0.0465 (3)−0.0349 (3)
S20.0382 (3)0.0311 (2)0.0292 (2)−0.0051 (2)0.01702 (19)−0.00241 (18)
O40.0416 (8)0.0312 (7)0.0379 (7)−0.0097 (6)0.0262 (6)−0.0099 (5)
O50.0321 (7)0.0342 (7)0.0421 (7)−0.0038 (6)0.0213 (6)−0.0107 (6)
N40.0285 (8)0.0358 (9)0.0408 (9)−0.0061 (7)0.0220 (7)−0.0108 (7)
N50.0286 (8)0.0410 (9)0.0469 (10)−0.0097 (7)0.0236 (8)−0.0147 (8)
N60.0321 (8)0.0409 (9)0.0383 (9)−0.0131 (7)0.0209 (7)−0.0153 (7)
C220.0308 (9)0.0255 (8)0.0333 (9)0.0023 (7)0.0198 (8)−0.0028 (7)
C230.0417 (11)0.0321 (10)0.0403 (10)−0.0023 (8)0.0254 (9)−0.0006 (8)
C240.0561 (13)0.0348 (10)0.0388 (11)0.0084 (10)0.0240 (10)0.0056 (8)
C250.0405 (11)0.0437 (11)0.0367 (10)0.0119 (9)0.0151 (9)0.0004 (9)
C260.0325 (10)0.0427 (11)0.0410 (11)0.0001 (9)0.0142 (9)−0.0042 (9)
C270.0342 (10)0.0309 (9)0.0346 (9)−0.0002 (8)0.0181 (8)−0.0008 (8)
C280.0300 (9)0.0256 (8)0.0320 (9)−0.0041 (7)0.0187 (8)−0.0048 (7)
C290.0290 (9)0.0344 (10)0.0292 (9)−0.0082 (8)0.0128 (8)−0.0026 (7)
C300.0503 (13)0.0486 (13)0.0564 (13)0.0089 (11)0.0312 (11)0.0164 (10)
C310.0720 (18)0.0561 (15)0.0774 (18)0.0105 (13)0.0405 (15)0.0305 (13)
C320.0647 (16)0.0634 (16)0.0495 (13)−0.0112 (13)0.0269 (12)0.0180 (12)
C330.0462 (12)0.0634 (15)0.0388 (11)−0.0239 (11)0.0263 (10)−0.0105 (10)
C340.0359 (10)0.0413 (11)0.0362 (10)−0.0119 (9)0.0191 (9)−0.0072 (8)
C350.0280 (9)0.0307 (9)0.0305 (9)−0.0016 (7)0.0158 (8)0.0004 (7)
C360.0277 (9)0.0332 (9)0.0281 (9)−0.0036 (7)0.0127 (7)0.0005 (7)
C370.0275 (9)0.0297 (9)0.0328 (9)−0.0052 (7)0.0156 (7)−0.0037 (7)
C380.0361 (11)0.0634 (14)0.0296 (9)−0.0134 (10)0.0168 (8)−0.0048 (9)
C390.0356 (11)0.0711 (15)0.0358 (10)−0.0169 (11)0.0155 (9)−0.0188 (10)
C400.0312 (10)0.0364 (10)0.0499 (11)−0.0102 (8)0.0246 (9)−0.0121 (9)
C410.0377 (10)0.0293 (9)0.0376 (10)0.0009 (8)0.0234 (8)0.0019 (7)
C420.0298 (9)0.0333 (9)0.0261 (8)0.0015 (8)0.0114 (7)−0.0005 (7)

Geometric parameters (Å, °)

Cl1—C191.7407 (18)Cl2—C401.7445 (19)
S1—C151.6791 (18)S2—C361.6824 (19)
O1—C71.435 (2)O4—C281.439 (2)
O1—H1O0.8400O4—H4O0.8400
O2—C141.241 (2)O5—C351.242 (2)
N1—C141.323 (2)N4—C351.327 (2)
N1—N21.383 (2)N4—N51.380 (2)
N1—H1N0.89 (2)N4—H4N0.88 (2)
N2—C151.349 (2)N5—C361.351 (2)
N2—H2N0.81 (2)N5—H5N0.90 (2)
N3—C151.355 (2)N6—C361.345 (2)
N3—C161.417 (2)N6—C371.421 (2)
N3—H3N0.88 (2)N6—H6N0.89 (2)
C1—C21.391 (2)C22—C271.385 (2)
C1—C61.394 (3)C22—C231.397 (3)
C1—C71.535 (2)C22—C281.532 (3)
C2—C31.386 (3)C23—C241.386 (3)
C2—H20.9500C23—H230.9500
C3—C41.380 (3)C24—C251.383 (3)
C3—H30.9500C24—H240.9500
C4—C51.379 (3)C25—C261.381 (3)
C4—H4A0.9500C25—H250.9500
C5—C61.387 (3)C26—C271.392 (3)
C5—H50.9500C26—H260.9500
C6—H60.9500C27—H270.9500
C7—C81.530 (2)C28—C291.525 (2)
C7—C141.537 (2)C28—C351.545 (2)
C8—C91.387 (3)C29—C301.390 (3)
C8—C131.398 (3)C29—C341.394 (3)
C9—C101.389 (3)C30—C311.385 (3)
C9—H90.9500C30—H300.9500
C10—C111.389 (3)C31—C321.372 (4)
C10—H100.9500C31—H310.9500
C11—C121.374 (3)C32—C331.380 (3)
C11—H110.9500C32—H320.9500
C12—C131.389 (3)C33—C341.393 (3)
C12—H120.9500C33—H330.9500
C13—H130.9500C34—H340.9500
C16—C211.388 (2)C37—C381.380 (3)
C16—C171.393 (2)C37—C421.387 (2)
C17—C181.390 (2)C38—C391.390 (3)
C17—H170.9500C38—H380.9500
C18—C191.379 (3)C39—C401.375 (3)
C18—H180.9500C39—H390.9500
C19—C201.378 (3)C40—C411.377 (3)
C20—C211.386 (3)C41—C421.383 (2)
C20—H200.9500C41—H410.9500
C21—H210.9500C42—H420.9500
C7—O1—H1O109.5C28—O4—H4O109.5
C14—N1—N2120.78 (16)C35—N4—N5120.94 (16)
C14—N1—H1N123.6 (14)C35—N4—H4N123.9 (15)
N2—N1—H1N115.2 (14)N5—N4—H4N114.8 (15)
C15—N2—N1119.41 (16)C36—N5—N4120.32 (16)
C15—N2—H2N123.1 (17)C36—N5—H5N123.2 (15)
N1—N2—H2N117.5 (17)N4—N5—H5N115.4 (15)
C15—N3—C16130.79 (15)C36—N6—C37128.29 (16)
C15—N3—H3N115.2 (13)C36—N6—H6N116.9 (14)
C16—N3—H3N114.0 (13)C37—N6—H6N114.7 (14)
C2—C1—C6118.51 (17)C27—C22—C23118.62 (17)
C2—C1—C7121.52 (16)C27—C22—C28123.20 (16)
C6—C1—C7119.94 (16)C23—C22—C28118.18 (16)
C3—C2—C1120.69 (18)C24—C23—C22120.55 (18)
C3—C2—H2119.7C24—C23—H23119.7
C1—C2—H2119.7C22—C23—H23119.7
C4—C3—C2120.20 (19)C25—C24—C23120.42 (19)
C4—C3—H3119.9C25—C24—H24119.8
C2—C3—H3119.9C23—C24—H24119.8
C5—C4—C3119.79 (19)C26—C25—C24119.42 (19)
C5—C4—H4A120.1C26—C25—H25120.3
C3—C4—H4A120.1C24—C25—H25120.3
C4—C5—C6120.30 (19)C25—C26—C27120.40 (19)
C4—C5—H5119.9C25—C26—H26119.8
C6—C5—H5119.9C27—C26—H26119.8
C5—C6—C1120.49 (18)C22—C27—C26120.58 (18)
C5—C6—H6119.8C22—C27—H27119.7
C1—C6—H6119.8C26—C27—H27119.7
O1—C7—C8111.13 (14)O4—C28—C29110.30 (14)
O1—C7—C1108.97 (14)O4—C28—C22108.47 (14)
C8—C7—C1111.45 (14)C29—C28—C22113.96 (14)
O1—C7—C14106.27 (13)O4—C28—C35105.77 (13)
C8—C7—C14111.82 (15)C29—C28—C35110.80 (14)
C1—C7—C14106.96 (13)C22—C28—C35107.16 (13)
C9—C8—C13118.70 (18)C30—C29—C34118.53 (18)
C9—C8—C7124.01 (17)C30—C29—C28122.81 (17)
C13—C8—C7117.28 (17)C34—C29—C28118.63 (17)
C8—C9—C10120.5 (2)C31—C30—C29120.7 (2)
C8—C9—H9119.8C31—C30—H30119.6
C10—C9—H9119.8C29—C30—H30119.6
C9—C10—C11120.3 (2)C32—C31—C30120.3 (2)
C9—C10—H10119.8C32—C31—H31119.9
C11—C10—H10119.8C30—C31—H31119.9
C12—C11—C10119.7 (2)C31—C32—C33120.1 (2)
C12—C11—H11120.2C31—C32—H32119.9
C10—C11—H11120.2C33—C32—H32119.9
C11—C12—C13120.3 (2)C32—C33—C34119.9 (2)
C11—C12—H12119.8C32—C33—H33120.1
C13—C12—H12119.8C34—C33—H33120.1
C12—C13—C8120.5 (2)C33—C34—C29120.5 (2)
C12—C13—H13119.7C33—C34—H34119.8
C8—C13—H13119.7C29—C34—H34119.8
O2—C14—N1122.43 (16)O5—C35—N4123.06 (16)
O2—C14—C7123.19 (15)O5—C35—C28123.25 (15)
N1—C14—C7114.37 (15)N4—C35—C28113.68 (15)
N2—C15—N3111.80 (15)N6—C36—N5112.18 (16)
N2—C15—S1121.19 (13)N6—C36—S2125.65 (14)
N3—C15—S1127.00 (13)N5—C36—S2122.17 (14)
C21—C16—C17119.19 (16)C38—C37—C42119.58 (17)
C21—C16—N3115.52 (15)C38—C37—N6122.87 (16)
C17—C16—N3125.15 (16)C42—C37—N6117.42 (16)
C18—C17—C16119.30 (17)C37—C38—C39119.87 (18)
C18—C17—H17120.3C37—C38—H38120.1
C16—C17—H17120.3C39—C38—H38120.1
C19—C18—C17120.72 (17)C40—C39—C38119.69 (18)
C19—C18—H18119.6C40—C39—H39120.2
C17—C18—H18119.6C38—C39—H39120.2
C20—C19—C18120.42 (17)C39—C40—C41121.18 (17)
C20—C19—Cl1119.79 (15)C39—C40—Cl2119.50 (16)
C18—C19—Cl1119.79 (14)C41—C40—Cl2119.31 (15)
C19—C20—C21119.10 (18)C40—C41—C42118.90 (17)
C19—C20—H20120.4C40—C41—H41120.5
C21—C20—H20120.4C42—C41—H41120.5
C20—C21—C16121.25 (18)C41—C42—C37120.77 (17)
C20—C21—H21119.4C41—C42—H42119.6
C16—C21—H21119.4C37—C42—H42119.6
C14—N1—N2—C15−176.39 (17)C35—N4—N5—C36171.09 (17)
C6—C1—C2—C31.0 (3)C27—C22—C23—C240.4 (3)
C7—C1—C2—C3179.43 (16)C28—C22—C23—C24−179.29 (16)
C1—C2—C3—C40.5 (3)C22—C23—C24—C25−0.5 (3)
C2—C3—C4—C5−1.5 (3)C23—C24—C25—C260.2 (3)
C3—C4—C5—C61.0 (3)C24—C25—C26—C270.3 (3)
C4—C5—C6—C10.5 (3)C23—C22—C27—C260.0 (3)
C2—C1—C6—C5−1.5 (3)C28—C22—C27—C26179.73 (16)
C7—C1—C6—C5−179.97 (17)C25—C26—C27—C22−0.4 (3)
C2—C1—C7—O1153.48 (15)C27—C22—C28—O4−130.14 (17)
C6—C1—C7—O1−28.1 (2)C23—C22—C28—O449.6 (2)
C2—C1—C7—C830.5 (2)C27—C22—C28—C29−6.9 (2)
C6—C1—C7—C8−151.15 (16)C23—C22—C28—C29172.85 (15)
C2—C1—C7—C14−92.03 (19)C27—C22—C28—C35116.09 (18)
C6—C1—C7—C1486.35 (19)C23—C22—C28—C35−64.21 (19)
O1—C7—C8—C9122.7 (2)O4—C28—C29—C30−119.9 (2)
C1—C7—C8—C9−115.6 (2)C22—C28—C29—C30117.8 (2)
C14—C7—C8—C94.1 (2)C35—C28—C29—C30−3.1 (2)
O1—C7—C8—C13−58.3 (2)O4—C28—C29—C3458.3 (2)
C1—C7—C8—C1363.5 (2)C22—C28—C29—C34−64.0 (2)
C14—C7—C8—C13−176.87 (15)C35—C28—C29—C34175.04 (15)
C13—C8—C9—C10−0.2 (3)C34—C29—C30—C310.1 (3)
C7—C8—C9—C10178.8 (2)C28—C29—C30—C31178.3 (2)
C8—C9—C10—C110.8 (4)C29—C30—C31—C32−0.1 (4)
C9—C10—C11—C12−0.6 (4)C30—C31—C32—C33−0.1 (4)
C10—C11—C12—C13−0.3 (4)C31—C32—C33—C340.3 (4)
C11—C12—C13—C80.9 (3)C32—C33—C34—C29−0.4 (3)
C9—C8—C13—C12−0.6 (3)C30—C29—C34—C330.1 (3)
C7—C8—C13—C12−179.73 (17)C28—C29—C34—C33−178.10 (17)
N2—N1—C14—O2−4.2 (3)N5—N4—C35—O52.4 (3)
N2—N1—C14—C7175.22 (16)N5—N4—C35—C28−176.98 (16)
O1—C7—C14—O2171.68 (16)O4—C28—C35—O5−169.03 (16)
C8—C7—C14—O2−66.9 (2)C29—C28—C35—O571.4 (2)
C1—C7—C14—O255.4 (2)C22—C28—C35—O5−53.4 (2)
O1—C7—C14—N1−7.7 (2)O4—C28—C35—N410.4 (2)
C8—C7—C14—N1113.68 (17)C29—C28—C35—N4−109.15 (17)
C1—C7—C14—N1−124.05 (16)C22—C28—C35—N4125.97 (16)
N1—N2—C15—N3179.07 (15)C37—N6—C36—N5−178.74 (18)
N1—N2—C15—S1−1.2 (2)C37—N6—C36—S22.3 (3)
C16—N3—C15—N2−178.13 (16)N4—N5—C36—N6−171.84 (17)
C16—N3—C15—S12.2 (3)N4—N5—C36—S27.1 (3)
C15—N3—C16—C21−165.17 (18)C36—N6—C37—C3849.5 (3)
C15—N3—C16—C1719.2 (3)C36—N6—C37—C42−134.7 (2)
C21—C16—C17—C180.9 (3)C42—C37—C38—C39−0.6 (3)
N3—C16—C17—C18176.41 (16)N6—C37—C38—C39175.2 (2)
C16—C17—C18—C19−0.7 (3)C37—C38—C39—C400.0 (3)
C17—C18—C19—C20−0.4 (3)C38—C39—C40—C410.3 (3)
C17—C18—C19—Cl1−179.70 (14)C38—C39—C40—Cl2−178.71 (18)
C18—C19—C20—C211.3 (3)C39—C40—C41—C420.0 (3)
Cl1—C19—C20—C21−179.38 (16)Cl2—C40—C41—C42179.06 (14)
C19—C20—C21—C16−1.1 (3)C40—C41—C42—C37−0.7 (3)
C17—C16—C21—C200.0 (3)C38—C37—C42—C411.0 (3)
N3—C16—C21—C20−175.90 (19)N6—C37—C42—C41−175.05 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1O···S2i0.842.443.2242 (13)156
N1—H1N···S10.89 (2)2.44 (2)2.9075 (16)113.5 (17)
N2—H2N···O5ii0.81 (2)2.12 (2)2.870 (2)155 (2)
N3—H3N···O5ii0.88 (2)2.17 (2)3.003 (2)156.1 (18)
O4—H4O···S1iii0.842.513.2707 (13)151
N4—H4N···S20.88 (2)2.50 (2)2.9569 (16)113.5 (17)
N5—H5N···O2iv0.90 (2)1.96 (2)2.776 (2)149 (2)
N6—H6N···O2iv0.89 (2)2.02 (2)2.842 (2)154 (2)

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, y, z+1; (iii) x, −y+3/2, z−1/2; (iv) x, y, z−1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2559).

References

  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Bruker (1996). XSCANS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2005). SADABS Bruker AXS Inc. Madison, Wisconsin, USA.
  • Ergenç, N., Ilhan, E. & Ötük, G. (1992). Pharmazie, 47, 59–60. [PubMed]
  • Jalilian, A. R., Sattari, S., Bineshmarvasti, M., Shafiee, A. & Daneshtalab, M. (2000). Arch. Pharm. Pharm. Med. Chem.333, 347–354. [PubMed]
  • John, A. D. (1998). Lang’s Handbook of Chemistry, 4, pp. 39-41. New York: McGraw-Hill.
  • Kucukguzel, G., Kocatepa, A., DeClercq, E., Sahin, F. & Gulluce, M. (2006). Eur. J. Med. Chem.41, 353–359. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Shen, X., Shi, X., Kang, B., Liu, Y., Tong, Y., Jiang, H. & Chen, K. (1998). Polyhedron, 17, 4049–4058.
  • Singh, S., Husain, K., Athar, F. & Azam, A. (2005). Eur. J. Pharm. Sci.25, 255–262. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography