share
share
Issue contentsclose
Statistics
close
Download citation
closeDownload citation
Format BIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Text
Plain Text
Supporting information
Supporting informationclose
Download PDF of article
Download PDF of articleclose
Acta Cryst. (2007). E63, o2681
https://doi.org/10.1107/S1600536807019678
Download PDF of article
Download PDF of articleclose
Supporting information
Supporting informationclose
Download citation
closeDownload citation
Format BIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Text
Plain Text
Statistics
close
Issue contentsclose
share
link to html

The Schiff base 11-thio­semi­carbazono­indeno[1,2-b]quinoxaline-8-carboxylic acid dimethyl sulfoxide solvate

X.-Q. Che and L.-B. Wang
In the title Schiff base compound, C17H28N5O2S·C2H6OS, all atoms in the Schiff base are nearly coplanar. There are two similar mol­ecules of the Schiff base and two dimethyl sulfoxide solvent mol­ecules in the asymmetric unit. The crystal packing is stabilized by N—H...O and N—H...N hydrogen-bond inter­actions. One solvent S atom is disordered over two positions in approximately a 4:1 ratio; the other solvent S atom is disordered over two positions in approximately a 7:1 ratio.
Read articleSimilar articles

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807019678/fl2127sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807019678/fl2127Isup2.hkl
Contains datablock I

CCDC reference: 647691

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • H-atom completeness 65%
  • Disorder in solvent or counterion
  • R factor = 0.067
  • wR factor = 0.198
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found




Alert level B
PLAT221_ALERT_4_B Large Solvent/Anion  S     Ueq(max)/Ueq(min) ...       4.51 Ratio


Alert level C
CHEMW03_ALERT_2_C The ratio of given/expected molecular weight as
            calculated from the _atom_site* data lies outside
            the range 0.99 <> 1.01
           From the CIF: _cell_formula_units_Z                    8
           From the CIF: _chemical_formula_weight           427.50
           TEST: Calculate formula weight from _atom_site_*
           atom     mass    num     sum
           C        12.01   19.00  228.21
           H         1.01   11.00   11.09
           N        14.01    5.00   70.04
           O        16.00    3.00   48.00
           S        32.07    2.00   64.13
           Calculated formula weight              421.46
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT043_ALERT_1_C Check Reported Molecular Weight ................     427.50
PLAT044_ALERT_1_C Calculated and Reported Dx Differ ..............          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.03
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C18
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        C35
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        S3'
PLAT243_ALERT_4_C High  'Solvent' Ueq as Compared to Neighbors for        S4'
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         S3
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         O5
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         S4
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         O6
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C38
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      20.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      42.00 Deg.
              S3   -C35  -S3'     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      44.50 Deg.
              S3'  -C36  -S3      1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      37.30 Deg.
              S4'  -C37  -S4      1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      36.70 Deg.
              S4   -C38  -S4'     1.555   1.555   1.555


Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C19 H17 N5 O3 S2
            Atom count from _chemical_formula_moiety:C19 H34 N5 O3 S2
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C19 H17 N5 O3 S2
            Atom count from the _atom_site data:  C19 H11 N5 O3 S2
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    8
           From the CIF: _chemical_formula_sum  C19 H17 N5 O3 S2
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        152.00    152.00    0.00
           H        136.00     88.00   48.00
           N         40.00     40.00    0.00
           O         24.00     24.00    0.00
           S         16.00     16.00    0.00
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K


   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  25 ALERT level C = Check and explain
   6 ALERT level G = General alerts; check

  11 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
  11 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check
Comment top

The thiosemicarbazide Schiff-base and its complexes are particularly widely studied because they are not only organic colorants with excellent performance and antibacterial & antiviral biological activities, but also templates for studying biocatalytic activity (Singh et al., 1978; Javad et al., 2005), but there are few studies of thiosemicarbazide Schiff-base synthesis (Rao et al., 1984a; Rao et al., 1984b). Recently, we have reported a crystal structure of the title compound (I) zinc complex (Che et al., 2006). Here we present crystal structure of (I).

There are two similar molecules of (I) and two DMSO solvent molecules in the asymmetric unit (Fig. 1). Bond distances and angles are very similar to the our previously reported zinc complex of (I) (Che et al., 2006). In the zinc complex of (I), each ligand (I) anion, which lost two H atoms on N2 and carboxyl O1, has two parts. One part, acting in tridentate chelating mode, coordinates to one ZnII through N2, N4 and S1, while another part coordinates to another ZnII through a monodentate carboxyl group. In the present Schiff-base (I), the H atoms on N2 and O1 are not lost. The N2 atom is also in the cis position with respect to N4 in the quinoxaline ring. All atoms (except the H atoms) in the molecule are nearly planar (the mean deviation of the atoms from the least-squares plane is 0.0590 Å). The crystal packing of (I) is stabilized by intermolecular N—H···O and N—H···N hydrogen-bond interactions (Table 1).

Related literature top

For related literature, see: Che et al. (2006). For a similar crystal structure; Javad et al. (2005) and Singh et al. (1978). For synthesis, see: Rao, Kumar & Rao (1984); Rao, Rao & Girisham (1984).

Experimental top

All reagents were purchased (Adrich) and used without further purification. Compound (I) was synthesized according to the reference (Rao et al., 1984a). Then compound (I) (0.698 g, 0.002 mol) was dissolved into 20 ml DMSO. After heating at 70 °C for 20 min, the mixture was allowed to cool and evaporate naturally. Yellow block crystals of (I) suitable for single-crystal X-ray diffraction were obtained by evaporating the mixture at room temperature for a period of two weeks. Analysis found: C 53.5, H 4.0, N 16.4, S 14.8%; C19H17N5O3S2 requires: C 53.38, H 4.01, N 16.38, S 15.00%.

Refinement top

H atoms were generated geometrically and refined as riding atoms with C—H= 0.93 Å (CH), C—H= 0.96 Å (CH3), N—H= 0.86 Å (NH and NH2), Uiso(H)= 1.2 times Ueq(C) or Ueq(N) for CH, NH and NH2, Uiso(H)= 1.5 times Ueq(C) for CH3. The S3 snd s4 atom in the solvent DMSO molecules were disordered with refined occupancies of 0.805, 0.195 and 0.871, 0.129, respectively. Standard DFIX restraints were used for the dimensions of the disordered DMSO. The S atoms of the minor orientation were refined with an overall Uiso value. The H atoms attached to the disordered DMSO molecules were not located. All other non-H atoms were refined anisotropically. The maximum positive peak of 0.42 e Å-3 in the final difference electron density map is located 1.06 (1) Å from atom S4.

Structure description top

The thiosemicarbazide Schiff-base and its complexes are particularly widely studied because they are not only organic colorants with excellent performance and antibacterial & antiviral biological activities, but also templates for studying biocatalytic activity (Singh et al., 1978; Javad et al., 2005), but there are few studies of thiosemicarbazide Schiff-base synthesis (Rao et al., 1984a; Rao et al., 1984b). Recently, we have reported a crystal structure of the title compound (I) zinc complex (Che et al., 2006). Here we present crystal structure of (I).

There are two similar molecules of (I) and two DMSO solvent molecules in the asymmetric unit (Fig. 1). Bond distances and angles are very similar to the our previously reported zinc complex of (I) (Che et al., 2006). In the zinc complex of (I), each ligand (I) anion, which lost two H atoms on N2 and carboxyl O1, has two parts. One part, acting in tridentate chelating mode, coordinates to one ZnII through N2, N4 and S1, while another part coordinates to another ZnII through a monodentate carboxyl group. In the present Schiff-base (I), the H atoms on N2 and O1 are not lost. The N2 atom is also in the cis position with respect to N4 in the quinoxaline ring. All atoms (except the H atoms) in the molecule are nearly planar (the mean deviation of the atoms from the least-squares plane is 0.0590 Å). The crystal packing of (I) is stabilized by intermolecular N—H···O and N—H···N hydrogen-bond interactions (Table 1).

For related literature, see: Che et al. (2006). For a similar crystal structure; Javad et al. (2005) and Singh et al. (1978). For synthesis, see: Rao, Kumar & Rao (1984); Rao, Rao & Girisham (1984).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1]
Scheme 1. Chemical structure.

Fig. 1. The asymmetric unit of (I) with the atom labeling scheme. Displacement ellipsoids are shown at the 30% probability level. Only the major orientation of the disordered DMSO molecule are shown. The hydrogen-bond interactions are drawn with dashed lines. Symmetry codes: (i) -x + 1,y - 1/2,-z + 3/2 (ii) -x + 1,-y + 1,-z + 2 (iii) -x,-y + 1,-z + 1 (iv) -x,-y + 1,-z (v) x,y,z - 1 (vi) x,-y + 3/2,z + 1/2.
11-thiosemicarbazonoindeno[1,2-b]quinoxaline-8-carboxylic acid dimethyl sulfoxide solvate top
Crystal data top
C17H28N5O2S·C2H6OSF(000) = 1776
Mr = 427.50Dx = 1.381 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 14.876 (2) ÅCell parameters from 2329 reflections
b = 25.205 (3) Åθ = 2.3–19.3°
c = 11.0201 (15) ŵ = 0.29 mm−1
β = 95.775 (3)°T = 293 K
V = 4111.0 (10) Å3Block, yellow
Z = 80.43 × 0.15 × 0.15 mm
Data collection top
Bruker SMART APEX2 CCD
diffractometer		7290 independent reflections
Radiation source: fine-focus sealed tube4399 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
φ and ω scansθmax = 25.1°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		h = −17→16
Tmin = 0.888, Tmax = 0.958k = −23→30
21346 measured reflectionsl = −12→13
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.198H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0964P)2 + 0.2132P]
where P = (Fo2 + 2Fc2)/3
7290 reflections(Δ/σ)max < 0.001
535 parametersΔρmax = 0.42 e Å−3
18 restraintsΔρmin = −0.21 e Å−3
Crystal data top
C17H28N5O2S·C2H6OSV = 4111.0 (10) Å3
Mr = 427.50Z = 8
Monoclinic, P21/cMo Kα radiation
a = 14.876 (2) ŵ = 0.29 mm−1
b = 25.205 (3) ÅT = 293 K
c = 11.0201 (15) Å0.43 × 0.15 × 0.15 mm
β = 95.775 (3)°
Data collection top
Bruker SMART APEX2 CCD
diffractometer		7290 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		4399 reflections with I > 2σ(I)
Tmin = 0.888, Tmax = 0.958Rint = 0.051
21346 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06718 restraints
wR(F2) = 0.198H-atom parameters constrained
S = 1.04Δρmax = 0.42 e Å−3
7290 reflectionsΔρmin = −0.21 e Å−3
535 parameters
Special details top

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) top
xyzUiso*/UeqOcc. (<1)
S30.24586 (9)0.74512 (5)0.94383 (12)0.0586 (6)0.805 (5)
S40.24527 (11)0.29402 (6)0.40349 (11)0.0670 (7)0.871 (5)
S3'0.3110 (16)0.7249 (8)1.010 (2)0.264 (10)*0.195 (5)
S4'0.1896 (15)0.2639 (9)0.4082 (17)0.162 (9)*0.129 (5)
N1−0.0339 (2)0.61471 (15)0.6245 (3)0.0728 (10)
H1A−0.05350.58380.60170.087*
H1B−0.05230.64240.58360.087*
N20.0507 (2)0.57418 (13)0.7820 (3)0.0549 (8)
H20.08740.57610.84740.066*
N30.0204 (2)0.52559 (13)0.7415 (3)0.0530 (8)
N40.13007 (19)0.52554 (11)0.9956 (3)0.0450 (7)
N50.1421 (2)0.41785 (12)1.0816 (3)0.0582 (9)
N60.5545 (2)0.34561 (14)0.3731 (3)0.0725 (11)
H6A0.57180.37600.40210.087*
H6B0.57720.31710.40610.087*
N70.4613 (2)0.38960 (11)0.2319 (3)0.0518 (8)
H7N0.42220.39010.16880.062*
N80.49081 (19)0.43564 (12)0.2853 (3)0.0463 (8)
N90.37777 (18)0.45074 (11)0.0357 (2)0.0420 (7)
N100.37666 (19)0.56254 (11)−0.0212 (3)0.0465 (8)
O10.2779 (2)0.63300 (12)1.3327 (3)0.0755 (9)
H10.29400.65511.38490.113*
O20.3298 (2)0.57660 (12)1.4791 (3)0.0819 (10)
O30.1741 (2)0.42962 (13)−0.4565 (2)0.0813 (10)
O40.2167 (2)0.36383 (11)−0.3284 (2)0.0666 (8)
H40.19620.3455−0.38620.100*
O50.3139 (2)0.78780 (12)0.9794 (3)0.0979 (12)
O60.1697 (2)0.29926 (12)0.4872 (3)0.0801 (9)
S10.06694 (10)0.67658 (5)0.77726 (13)0.0971 (5)
S20.45768 (10)0.28637 (5)0.21016 (13)0.0931 (5)
C10.0248 (3)0.61963 (16)0.7224 (4)0.0575 (11)
C20.0437 (2)0.48613 (16)0.8122 (4)0.0497 (10)
C30.0197 (3)0.43073 (17)0.7843 (4)0.0589 (11)
C4−0.0273 (3)0.40903 (19)0.6791 (4)0.0700 (13)
H4A−0.04830.43060.61370.084*
C5−0.0416 (3)0.3553 (2)0.6751 (6)0.0921 (17)
H5−0.07190.34020.60560.111*
C6−0.0116 (4)0.3230 (2)0.7735 (6)0.0954 (18)
H6−0.02330.28670.76900.114*
C70.0357 (3)0.34383 (18)0.8793 (5)0.0808 (14)
H70.05540.32210.94500.097*
C80.0523 (3)0.39833 (16)0.8825 (4)0.0585 (11)
C90.0995 (2)0.43138 (15)0.9757 (4)0.0517 (10)
C100.0951 (2)0.48527 (15)0.9334 (3)0.0473 (9)
C110.1742 (2)0.51258 (14)1.1071 (3)0.0432 (9)
C120.1806 (3)0.45922 (15)1.1484 (3)0.0509 (10)
C130.2272 (3)0.44885 (17)1.2644 (4)0.0619 (11)
H130.23320.41411.29230.074*
C140.2633 (3)0.48922 (17)1.3356 (4)0.0577 (11)
H140.29350.48161.41160.069*
C150.2557 (2)0.54232 (16)1.2961 (3)0.0498 (9)
C160.2118 (2)0.55346 (15)1.1823 (3)0.0489 (9)
H160.20720.58841.15530.059*
C170.2914 (3)0.58507 (17)1.3783 (4)0.0581 (11)
C180.4934 (3)0.34274 (15)0.2781 (3)0.0549 (10)
C190.4676 (2)0.47900 (14)0.2286 (3)0.0414 (8)
C200.4953 (2)0.53187 (14)0.2728 (3)0.0437 (9)
C210.5442 (2)0.54663 (16)0.3814 (3)0.0529 (10)
H210.56410.52130.43930.063*
C220.5626 (3)0.59962 (17)0.4015 (4)0.0605 (11)
H220.59480.61020.47420.073*
C230.5337 (3)0.63772 (18)0.3143 (4)0.0695 (12)
H230.54720.67330.32950.083*
C240.4850 (3)0.62332 (16)0.2053 (4)0.0619 (11)
H240.46580.64880.14740.074*
C250.4657 (2)0.57004 (14)0.1849 (3)0.0454 (9)
C260.4162 (2)0.54262 (14)0.0815 (3)0.0424 (9)
C270.4160 (2)0.48737 (14)0.1083 (3)0.0407 (8)
C280.3352 (2)0.47041 (14)−0.0723 (3)0.0408 (8)
C290.3351 (2)0.52530 (14)−0.0997 (3)0.0430 (9)
C300.2910 (2)0.54193 (15)−0.2124 (3)0.0514 (10)
H300.28960.5778−0.23240.062*
C310.2506 (2)0.50632 (17)−0.2914 (3)0.0526 (10)
H310.22180.5182−0.36520.063*
C320.2509 (2)0.45140 (15)−0.2652 (3)0.0478 (9)
C330.2926 (2)0.43428 (15)−0.1562 (3)0.0438 (9)
H330.29280.3983−0.13740.053*
C340.2103 (3)0.41428 (18)−0.3589 (3)0.0554 (11)
C350.2086 (7)0.7220 (3)1.0792 (7)0.180 (4)
C360.3075 (5)0.6881 (3)0.9071 (8)0.159 (3)
C370.2878 (4)0.2273 (2)0.4219 (5)0.114 (2)
C380.1898 (4)0.2855 (2)0.2531 (4)0.0961 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S30.0611 (10)0.0390 (8)0.0715 (10)−0.0050 (6)−0.0128 (7)0.0021 (6)
S40.0797 (12)0.0654 (10)0.0545 (8)−0.0086 (7)−0.0003 (7)−0.0078 (6)
N10.075 (3)0.078 (3)0.060 (2)0.000 (2)−0.0169 (19)0.0062 (19)
N20.050 (2)0.057 (2)0.0539 (19)−0.0005 (16)−0.0135 (15)−0.0034 (16)
N30.0436 (19)0.058 (2)0.057 (2)−0.0015 (16)0.0012 (16)−0.0157 (17)
N40.0408 (18)0.0445 (18)0.0500 (18)0.0012 (14)0.0062 (14)−0.0036 (15)
N50.057 (2)0.046 (2)0.074 (2)−0.0028 (16)0.0180 (19)0.0067 (18)
N60.092 (3)0.052 (2)0.066 (2)0.0160 (19)−0.024 (2)0.0004 (17)
N70.060 (2)0.0424 (19)0.0503 (18)−0.0031 (15)−0.0105 (15)−0.0024 (15)
N80.0474 (19)0.0464 (19)0.0440 (17)0.0010 (15)−0.0007 (14)−0.0046 (15)
N90.0411 (17)0.0447 (18)0.0398 (16)0.0014 (14)0.0030 (14)−0.0022 (14)
N100.0443 (18)0.0463 (18)0.0490 (18)0.0007 (14)0.0047 (15)0.0026 (15)
O10.087 (2)0.065 (2)0.070 (2)0.0067 (17)−0.0174 (17)−0.0044 (16)
O20.103 (3)0.081 (2)0.0570 (18)−0.0100 (18)−0.0135 (18)0.0059 (16)
O30.095 (2)0.100 (2)0.0446 (17)−0.0271 (18)−0.0159 (16)0.0102 (16)
O40.082 (2)0.065 (2)0.0500 (16)−0.0034 (16)−0.0073 (15)−0.0073 (15)
O50.120 (3)0.055 (2)0.108 (3)−0.0283 (18)−0.040 (2)0.0101 (18)
O60.101 (3)0.080 (2)0.0588 (17)0.0047 (18)0.0047 (17)−0.0224 (16)
S10.1048 (11)0.0569 (8)0.1182 (11)−0.0131 (7)−0.0446 (9)0.0123 (7)
S20.1140 (12)0.0498 (7)0.1095 (11)−0.0076 (7)−0.0181 (9)−0.0135 (7)
C10.048 (2)0.065 (3)0.057 (2)0.006 (2)−0.0068 (19)0.006 (2)
C20.035 (2)0.054 (3)0.061 (2)−0.0012 (18)0.0104 (18)−0.014 (2)
C30.037 (2)0.063 (3)0.079 (3)−0.0070 (19)0.016 (2)−0.021 (2)
C40.055 (3)0.073 (3)0.084 (3)−0.012 (2)0.013 (2)−0.030 (3)
C50.075 (4)0.088 (4)0.114 (5)−0.023 (3)0.018 (3)−0.045 (4)
C60.091 (4)0.067 (3)0.134 (5)−0.030 (3)0.039 (4)−0.043 (4)
C70.080 (3)0.060 (3)0.108 (4)−0.016 (3)0.032 (3)−0.013 (3)
C80.050 (3)0.053 (3)0.074 (3)−0.008 (2)0.019 (2)−0.011 (2)
C90.039 (2)0.047 (2)0.072 (3)−0.0016 (17)0.021 (2)−0.003 (2)
C100.035 (2)0.049 (2)0.059 (2)−0.0006 (17)0.0090 (18)−0.0066 (19)
C110.038 (2)0.048 (2)0.046 (2)0.0015 (16)0.0119 (17)0.0011 (18)
C120.049 (2)0.051 (2)0.055 (2)0.0004 (19)0.0156 (19)0.0034 (19)
C130.065 (3)0.060 (3)0.063 (3)0.001 (2)0.016 (2)0.020 (2)
C140.054 (3)0.069 (3)0.051 (2)0.000 (2)0.009 (2)0.014 (2)
C150.041 (2)0.060 (3)0.049 (2)−0.0007 (18)0.0080 (18)0.0031 (19)
C160.042 (2)0.052 (2)0.053 (2)0.0022 (18)0.0105 (18)0.0032 (19)
C170.053 (3)0.069 (3)0.052 (2)0.004 (2)0.005 (2)0.004 (2)
C180.063 (3)0.046 (2)0.055 (2)0.002 (2)0.003 (2)0.0006 (19)
C190.036 (2)0.049 (2)0.0389 (19)−0.0010 (16)0.0036 (16)−0.0031 (17)
C200.039 (2)0.046 (2)0.046 (2)0.0025 (17)0.0063 (17)−0.0060 (18)
C210.051 (2)0.057 (3)0.050 (2)−0.0055 (19)0.0042 (19)−0.0063 (19)
C220.056 (3)0.062 (3)0.063 (3)−0.005 (2)0.003 (2)−0.016 (2)
C230.061 (3)0.054 (3)0.092 (3)−0.007 (2)0.001 (2)−0.019 (3)
C240.058 (3)0.050 (3)0.076 (3)0.004 (2)−0.003 (2)0.000 (2)
C250.039 (2)0.045 (2)0.053 (2)0.0015 (16)0.0066 (17)−0.0046 (18)
C260.036 (2)0.043 (2)0.049 (2)0.0047 (16)0.0069 (17)0.0021 (17)
C270.035 (2)0.045 (2)0.043 (2)0.0020 (16)0.0082 (16)−0.0019 (17)
C280.037 (2)0.053 (2)0.0333 (19)0.0033 (16)0.0069 (16)0.0030 (16)
C290.041 (2)0.047 (2)0.042 (2)0.0038 (17)0.0078 (17)0.0026 (17)
C300.054 (2)0.051 (2)0.049 (2)0.0052 (19)0.0083 (19)0.0083 (19)
C310.047 (2)0.074 (3)0.037 (2)0.004 (2)0.0025 (18)0.008 (2)
C320.040 (2)0.063 (3)0.041 (2)−0.0038 (18)0.0080 (17)0.0012 (19)
C330.042 (2)0.051 (2)0.039 (2)−0.0021 (17)0.0023 (16)0.0004 (17)
C340.048 (2)0.082 (3)0.037 (2)−0.010 (2)0.0069 (18)0.001 (2)
C350.239 (10)0.180 (8)0.134 (6)−0.072 (7)0.082 (7)0.012 (6)
C360.131 (6)0.094 (5)0.251 (9)0.032 (4)0.014 (6)−0.070 (6)
C370.127 (5)0.107 (5)0.109 (4)0.054 (4)0.013 (4)0.018 (4)
C380.126 (5)0.110 (4)0.048 (3)0.014 (3)−0.007 (3)−0.007 (3)
Geometric parameters (Å, º) top
S3—O51.502 (3)C3—C41.403 (6)
S3—C351.743 (7)C4—C51.371 (7)
S3—C361.774 (6)C4—H4A0.9300
S4—O61.530 (3)C5—C61.393 (7)
S4—C381.788 (5)C5—H50.9300
S4—C371.800 (6)C6—C71.402 (7)
S3'—C361.46 (2)C6—H60.9300
S3'—O51.62 (2)C7—C81.395 (6)
S3'—C351.77 (2)C7—H70.9300
S4'—O61.301 (19)C8—C91.448 (5)
S4'—C371.721 (19)C9—C101.435 (5)
S4'—C381.794 (19)C11—C161.403 (5)
N1—C11.324 (5)C11—C121.420 (5)
N1—H1A0.8600C12—C131.416 (5)
N1—H1B0.8600C13—C141.362 (6)
N2—C11.357 (5)C13—H130.9300
N2—N31.364 (4)C14—C151.408 (5)
N2—H20.8600C14—H140.9300
N3—C21.289 (5)C15—C161.383 (5)
N4—C101.304 (4)C15—C171.472 (5)
N4—C111.373 (4)C16—H160.9300
N5—C91.316 (5)C19—C201.464 (5)
N5—C121.368 (5)C19—C271.477 (5)
N6—C181.318 (5)C20—C211.388 (5)
N6—H6A0.8600C20—C251.404 (5)
N6—H6B0.8600C21—C221.377 (5)
N7—C181.354 (4)C21—H210.9300
N7—N81.354 (4)C22—C231.396 (6)
N7—H7N0.8600C22—H220.9300
N8—C191.289 (4)C23—C241.387 (6)
N9—C271.314 (4)C23—H230.9300
N9—C281.383 (4)C24—C251.387 (5)
N10—C261.321 (4)C24—H240.9300
N10—C291.379 (4)C25—C261.466 (5)
O1—C171.316 (5)C26—C271.424 (5)
O1—H10.8200C28—C331.402 (5)
O2—C171.215 (5)C28—C291.416 (5)
O3—C341.216 (4)C29—C301.409 (5)
O4—C341.316 (5)C30—C311.349 (5)
O4—H40.8200C30—H300.9300
S1—C11.656 (4)C31—C321.414 (5)
S2—C181.668 (4)C31—H310.9300
C2—C31.466 (5)C32—C331.364 (5)
C2—C101.471 (5)C32—C341.478 (5)
C3—C81.403 (6)C33—H330.9300
O5—S3—C35106.3 (3)C14—C13—C12120.8 (4)
O5—S3—C36106.8 (3)C14—C13—H13119.6
C35—S3—C3698.0 (4)C12—C13—H13119.6
O6—S4—C38105.7 (2)C13—C14—C15121.1 (4)
O6—S4—C37106.5 (2)C13—C14—H14119.4
C38—S4—C3796.7 (3)C15—C14—H14119.4
C36—S3'—O5117.3 (15)C16—C15—C14119.3 (4)
C36—S3'—C35110.0 (14)C16—C15—C17121.2 (4)
O5—S3'—C35100.0 (12)C14—C15—C17119.5 (4)
O6—S4'—C37123.7 (15)C15—C16—C11120.7 (4)
O6—S4'—C38116.8 (14)C15—C16—H16119.7
C37—S4'—C3899.4 (10)C11—C16—H16119.7
C1—N1—H1A120.0O2—C17—O1123.4 (4)
C1—N1—H1B120.0O2—C17—C15122.8 (4)
H1A—N1—H1B120.0O1—C17—C15113.9 (3)
C1—N2—N3122.1 (3)N6—C18—N7116.1 (3)
C1—N2—H2119.0N6—C18—S2124.5 (3)
N3—N2—H2119.0N7—C18—S2119.3 (3)
C2—N3—N2115.8 (3)N8—C19—C20123.9 (3)
C10—N4—C11114.5 (3)N8—C19—C27130.2 (3)
C9—N5—C12114.7 (3)C20—C19—C27105.8 (3)
C18—N6—H6A120.0C21—C20—C25120.8 (3)
C18—N6—H6B120.0C21—C20—C19129.6 (3)
H6A—N6—H6B120.0C25—C20—C19109.6 (3)
C18—N7—N8119.8 (3)C22—C21—C20118.5 (4)
C18—N7—H7N120.1C22—C21—H21120.7
N8—N7—H7N120.1C20—C21—H21120.7
C19—N8—N7117.1 (3)C21—C22—C23120.9 (4)
C27—N9—C28113.9 (3)C21—C22—H22119.5
C26—N10—C29114.3 (3)C23—C22—H22119.5
C17—O1—H1109.5C24—C23—C22120.9 (4)
C34—O4—H4109.5C24—C23—H23119.5
S3—O5—S3'47.4 (9)C22—C23—H23119.5
S4'—O6—S446.1 (11)C23—C24—C25118.4 (4)
N1—C1—N2116.6 (4)C23—C24—H24120.8
N1—C1—S1125.0 (3)C25—C24—H24120.8
N2—C1—S1118.5 (3)C24—C25—C20120.4 (3)
N3—C2—C3124.3 (4)C24—C25—C26131.5 (4)
N3—C2—C10130.0 (3)C20—C25—C26108.1 (3)
C3—C2—C10105.6 (4)N10—C26—C27122.7 (3)
C8—C3—C4121.0 (4)N10—C26—C25129.2 (3)
C8—C3—C2109.6 (4)C27—C26—C25108.1 (3)
C4—C3—C2129.4 (4)N9—C27—C26124.8 (3)
C5—C4—C3118.3 (5)N9—C27—C19126.9 (3)
C5—C4—H4A120.8C26—C27—C19108.3 (3)
C3—C4—H4A120.8N9—C28—C33118.1 (3)
C4—C5—C6121.1 (5)N9—C28—C29121.6 (3)
C4—C5—H5119.5C33—C28—C29120.3 (3)
C6—C5—H5119.5N10—C29—C30119.3 (3)
C5—C6—C7121.5 (5)N10—C29—C28122.7 (3)
C5—C6—H6119.2C30—C29—C28117.9 (3)
C7—C6—H6119.2C31—C30—C29120.6 (4)
C8—C7—C6117.5 (5)C31—C30—H30119.7
C8—C7—H7121.2C29—C30—H30119.7
C6—C7—H7121.2C30—C31—C32121.8 (3)
C7—C8—C3120.5 (4)C30—C31—H31119.1
C7—C8—C9131.0 (4)C32—C31—H31119.1
C3—C8—C9108.5 (4)C33—C32—C31118.8 (3)
N5—C9—C10122.4 (4)C33—C32—C34122.2 (4)
N5—C9—C8129.5 (4)C31—C32—C34118.9 (3)
C10—C9—C8108.1 (4)C32—C33—C28120.6 (3)
N4—C10—C9124.2 (4)C32—C33—H33119.7
N4—C10—C2127.6 (3)C28—C33—H33119.7
C9—C10—C2108.2 (3)O3—C34—O4123.2 (4)
N4—C11—C16118.7 (3)O3—C34—C32122.0 (4)
N4—C11—C12121.5 (3)O4—C34—C32114.8 (3)
C16—C11—C12119.8 (3)S3—C35—S3'42.0 (8)
N5—C12—C13119.0 (4)S3'—C36—S344.5 (10)
N5—C12—C11122.6 (3)S4'—C37—S437.3 (8)
C13—C12—C11118.3 (4)S4—C38—S4'36.7 (8)
C1—N2—N3—C2−174.0 (3)N7—N8—C19—C27−3.4 (5)
C18—N7—N8—C19170.9 (3)N8—C19—C20—C21−4.5 (6)
C35—S3—O5—S3'61.9 (11)C27—C19—C20—C21179.2 (3)
C36—S3—O5—S3'−42.0 (10)N8—C19—C20—C25174.6 (3)
C36—S3'—O5—S361.0 (15)C27—C19—C20—C25−1.7 (4)
C35—S3'—O5—S3−57.7 (9)C25—C20—C21—C220.4 (5)
C37—S4'—O6—S462.5 (16)C19—C20—C21—C22179.4 (4)
C38—S4'—O6—S4−61.5 (13)C20—C21—C22—C23−0.6 (6)
C38—S4—O6—S4'54.8 (12)C21—C22—C23—C240.4 (6)
C37—S4—O6—S4'−47.3 (12)C22—C23—C24—C250.0 (6)
N3—N2—C1—N12.1 (6)C23—C24—C25—C20−0.2 (6)
N3—N2—C1—S1−178.7 (3)C23—C24—C25—C26179.5 (4)
N2—N3—C2—C3−178.7 (3)C21—C20—C25—C240.0 (5)
N2—N3—C2—C102.9 (6)C19—C20—C25—C24−179.2 (3)
N3—C2—C3—C8−177.5 (4)C21—C20—C25—C26−179.8 (3)
C10—C2—C3—C81.3 (4)C19—C20—C25—C261.0 (4)
N3—C2—C3—C43.0 (6)C29—N10—C26—C270.3 (5)
C10—C2—C3—C4−178.3 (4)C29—N10—C26—C25−179.7 (3)
C8—C3—C4—C50.7 (6)C24—C25—C26—N100.3 (7)
C2—C3—C4—C5−179.8 (4)C20—C25—C26—N10−179.9 (3)
C3—C4—C5—C61.0 (7)C24—C25—C26—C27−179.7 (4)
C4—C5—C6—C7−1.2 (8)C20—C25—C26—C270.1 (4)
C5—C6—C7—C8−0.3 (7)C28—N9—C27—C26−0.6 (5)
C6—C7—C8—C32.0 (6)C28—N9—C27—C19−179.0 (3)
C6—C7—C8—C9−179.0 (4)N10—C26—C27—N90.2 (5)
C4—C3—C8—C7−2.2 (6)C25—C26—C27—N9−179.9 (3)
C2—C3—C8—C7178.2 (3)N10—C26—C27—C19178.8 (3)
C4—C3—C8—C9178.6 (3)C25—C26—C27—C19−1.2 (4)
C2—C3—C8—C9−1.0 (4)N8—C19—C27—N94.4 (6)
C12—N5—C9—C100.8 (5)C20—C19—C27—N9−179.6 (3)
C12—N5—C9—C8179.4 (4)N8—C19—C27—C26−174.2 (3)
C7—C8—C9—N52.5 (7)C20—C19—C27—C261.8 (4)
C3—C8—C9—N5−178.4 (4)C27—N9—C28—C33179.7 (3)
C7—C8—C9—C10−178.7 (4)C27—N9—C28—C290.7 (5)
C3—C8—C9—C100.3 (4)C26—N10—C29—C30−179.8 (3)
C11—N4—C10—C91.0 (5)C26—N10—C29—C28−0.2 (5)
C11—N4—C10—C2179.7 (3)N9—C28—C29—N10−0.3 (5)
N5—C9—C10—N4−1.8 (6)C33—C28—C29—N10−179.3 (3)
C8—C9—C10—N4179.3 (3)N9—C28—C29—C30179.3 (3)
N5—C9—C10—C2179.3 (3)C33—C28—C29—C300.3 (5)
C8—C9—C10—C20.5 (4)N10—C29—C30—C31179.3 (3)
N3—C2—C10—N4−1.2 (6)C28—C29—C30—C31−0.4 (5)
C3—C2—C10—N4−179.8 (3)C29—C30—C31—C32−0.1 (6)
N3—C2—C10—C9177.6 (4)C30—C31—C32—C330.6 (5)
C3—C2—C10—C9−1.0 (4)C30—C31—C32—C34−176.3 (3)
C10—N4—C11—C16−178.1 (3)C31—C32—C33—C28−0.7 (5)
C10—N4—C11—C120.5 (5)C34—C32—C33—C28176.2 (3)
C9—N5—C12—C13179.3 (3)N9—C28—C33—C32−178.8 (3)
C9—N5—C12—C110.6 (5)C29—C28—C33—C320.2 (5)
N4—C11—C12—N5−1.4 (5)C33—C32—C34—O3−179.2 (4)
C16—C11—C12—N5177.2 (3)C31—C32—C34—O3−2.4 (6)
N4—C11—C12—C13180.0 (3)C33—C32—C34—O40.7 (5)
C16—C11—C12—C13−1.4 (5)C31—C32—C34—O4177.5 (3)
N5—C12—C13—C14−177.4 (4)O5—S3—C35—S3'−62.6 (10)
C11—C12—C13—C141.3 (6)C36—S3—C35—S3'47.7 (10)
C12—C13—C14—C15−0.2 (6)C36—S3'—C35—S3−70.8 (14)
C13—C14—C15—C16−0.9 (6)O5—S3'—C35—S353.3 (9)
C13—C14—C15—C17176.7 (4)O5—S3'—C36—S3−51.0 (12)
C14—C15—C16—C110.7 (5)C35—S3'—C36—S362.3 (12)
C17—C15—C16—C11−176.8 (3)O5—S3—C36—S3'51.1 (12)
N4—C11—C16—C15179.0 (3)C35—S3—C36—S3'−58.7 (12)
C12—C11—C16—C150.4 (5)O6—S4'—C37—S4−63.7 (18)
C16—C15—C17—O2179.6 (4)C38—S4'—C37—S467.7 (10)
C14—C15—C17—O22.1 (6)O6—S4—C37—S4'41.4 (10)
C16—C15—C17—O1−0.5 (5)C38—S4—C37—S4'−67.2 (11)
C14—C15—C17—O1−178.1 (3)O6—S4—C38—S4'−45.6 (10)
N8—N7—C18—N6−1.5 (5)C37—S4—C38—S4'63.7 (10)
N8—N7—C18—S2−179.0 (3)O6—S4'—C38—S464.9 (16)
N7—N8—C19—C20−178.8 (3)C37—S4'—C38—S4−70.7 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N7—H7N···N90.862.172.838 (4)134
N2—H2···N40.862.122.807 (4)137
N6—H6B···O5i0.862.092.820 (4)143
N6—H6A···O2ii0.862.212.982 (5)149
N1—H1B···O6iii0.862.363.131 (5)150
N1—H1A···O3iv0.862.302.872 (4)124
O4—H4···O6v0.821.832.642 (4)170
O1—H1···O5vi0.821.782.591 (4)168
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, −y+1, −z+2; (iii) −x, −y+1, −z+1; (iv) −x, −y+1, −z; (v) x, y, z−1; (vi) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC17H28N5O2S·C2H6OS
Mr427.50
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)14.876 (2), 25.205 (3), 11.0201 (15)
β (°) 95.775 (3)
V (Å3)4111.0 (10)
Z8
Radiation typeMo Kα
µ (mm−1)0.29
Crystal size (mm)0.43 × 0.15 × 0.15
Data collection
DiffractometerBruker SMART APEX2 CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2004)
Tmin, Tmax0.888, 0.958
No. of measured, independent and
observed [I > 2σ(I)] reflections		21346, 7290, 4399
Rint0.051
(sin θ/λ)max (Å−1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.067, 0.198, 1.04
No. of reflections7290
No. of parameters535
No. of restraints18
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.42, −0.21

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N7—H7N···N90.862.172.838 (4)133.7
N2—H2···N40.862.122.807 (4)136.8
N6—H6B···O5i0.862.092.820 (4)143.1
N6—H6A···O2ii0.862.212.982 (5)148.8
N1—H1B···O6iii0.862.363.131 (5)150.1
N1—H1A···O3iv0.862.302.872 (4)123.6
O4—H4···O6v0.821.832.642 (4)170.1
O1—H1···O5vi0.821.782.591 (4)168.1
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+1, −y+1, −z+2; (iii) −x, −y+1, −z+1; (iv) −x, −y+1, −z; (v) x, y, z−1; (vi) x, −y+3/2, z+1/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS