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Two mol­ecules of the title compound, 3,5,15,17-tetra­thia-7,13,24,25-tetra­aza­tetra­cyclo­[17.3.1.14,7.113,16]­penta­cosa-1(23),4(24),16(25),19,21-penta­ene-6,14-dione, C16H16N4O3S4, having slightly different hollow and curved conformations, form the asymmetric unit. Each mol­ecule provides an internal cavity of cage-like shape to form a host-guest complex.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801005116/cv6014sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801005116/cv6014Isup2.hkl
Contains datablock I

CCDC reference: 162834

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.061
  • wR factor = 0.142
  • Data-to-parameter ratio = 14.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_320 Alert C Check Hybridisation of S(8) in main residue ? PLAT_320 Alert C Check Hybridisation of S(20) in main residue ? PLAT_320 Alert C Check Hybridisation of S(35) in main residue ? PLAT_320 Alert C Check Hybridisation of S(47) in main residue ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
4 Alert Level C = Please check

Comment top

As a continuation of our studies relating to the synthesis of host compounds containing 5-mercapto-2,3-dihydro-1,3,4-thiadizol-2-ones (Cho, Park, Kim et al., 1999; Cho, Park, Hwang et al., 1999; Cho et al., 2000), we have prepared macrocycle (I) composed of two 5-mercapto-2,3-dihydro-1,3,4-thiadizol-2-ones and m-xylene. The determination of the structure of (I) is part of our interest in dealing with the macrocycles and this compound might be a potential host molecule for a palladium metal ion. Thus, we are in the progress of examining the role of this compound as an artificial receptor.

There are two molecules of (I) in the asymmetric unit. The S–C distances in the two molecules range from 1.720 (5) to 1.815 (5) Å, with a mean value of 1.766 (1) Å. The distances O25—C7 1.216 (5), O26—C21 1.207 (5), O52—C34 = 1.218 (5) and O53—C48 = 1.203 (5) Å clearly show double-bond character. These values are comparable with those found in 4,17,25,26-tetraaza-6,9,12,15-tetraoxa-2,19,21,24-tetrathiatricyclo- [18.4.11,4.117,20]hexacosa-1(25),20 (26)-diene-3,5,16,18-tetraone (Cho et al., 2000). The C—S—C angles in the five-membered rings range from 88.7 (2) to 89.9 (2)°, with a mean value of 89.1 (1)°, which is similiar to the value of 90.7 (1)° found in 2,3-dihydro-3-methyl-2-nitrimino-1,3-thiazole (Kyziol et al., 2000). All the five-membered rings are planar within 0.012 (3) Å, the two benzene rings are planar within 0.016 (3) Å and the two ethyl ether linkages are planar within 0.107 (3) Å. In the first molecule (Fig. 1), the dihedral angle between the five-membered rings N6/C7/S8/C9/N24 and C19/S20/C21/N22/N23 is 30.4 (2)°, with distances N6···N22 = 4.640 (5) Å, N23···N24 = 5.080 (5) Å, S10···S18 = 5.197 (2) Å and S8···S20 = 3.957 (2) Å, so that the two rings become narrower inwardly. The dihedral angle between benzene ring C12/C13/C14/C15/C16/C27 and ethyl ether linkage C1/C2/O3/C4/C5 is 37.35 (19)°, and they also become narrower inwardly, with a C4···C14 distance 4.125 (8) Å. In the second molecule (Fig. 1), the dihedral angle between the five-membered rings N33/C34/C35/C36/N51 and C46/S47/C48/N49/N50 is 30.5 (1)°, with distances N33···N49 = 4.561 (6) Å, N50···N51 = 5.015 (5) Å, S37···S45 = 5.111 (2) Å and S35···S47 = 3.812 (2) Å, and the dihedral angle between benzene ring C39/C40/C41/C42/C43/C54 and ethyl ether linkage C28/C29/O30/C31/C32 is 36.9 (2)°, becoming narrower inwardly with a C29···C41 distance of 4.125 (8) Å. Therefore, both molecules have a cage-like form with similiar conformations and each molecule appears to have sufficient space inside to introduce a guest atom into the molecule. The closest intermolecular distance is O26···H32A(1 - x, 0.5 + y, 0.5 - z) of 2.403 Å.

Experimental top

The preparation of (I) followed the general procedure previously reported by Cho, Park, Hwang et al. (1999). The details will be reported elsewhere.

Refinement top

All H atoms were placed in calculated positions [C—Hmethylene = 0.97 Å and C—Haromatic = 0.93 Å], with Uiso constrained to be 1.2 times the equivalent isotropic displacement parameter of the attached C atom. The highest peak and the deepest hole in the final difference density map are at 0.81 Å from H40 and 0.96 Å from S35, respectively.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonious, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. View of the two molecules (I) in the asymmetric unit, showing 20% probability displacement ellipsoids. C atoms are shown with ellipsoids with enveloping ellipses only and the remaining atoms are shown with ellipsoids with octant shading. H atoms have been omitted for clarity.
(I) top
Crystal data top
C16H16N4O3S4F(000) = 1824
Mr = 440.57Dx = 1.475 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
a = 16.827 (2) ÅCell parameters from 25 reflections
b = 14.1071 (16) Åθ = 11.3–12.7°
c = 16.760 (4) ŵ = 0.50 mm1
β = 93.950 (16)°T = 293 K
V = 3969.0 (12) Å3Plate, light brown
Z = 80.50 × 0.43 × 0.13 mm
Data collection top
Enraf-Nonious CAD4
diffractometer
3946 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.028
Graphite monochromatorθmax = 25.0°, θmin = 2.2°
non–profiled ω/2θ scansh = 019
Absorption correction: ψ scan
(North et al., 1968)
k = 016
Tmin = 0.779, Tmax = 0.936l = 1919
7087 measured reflections3 standard reflections every 300 min
6845 independent reflections intensity decay: none
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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0505P)2 + 1.381P]
where P = (Fo2 + 2Fc2)/3
6845 reflections(Δ/σ)max < 0.001
481 parametersΔρmax = 0.95 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C16H16N4O3S4V = 3969.0 (12) Å3
Mr = 440.57Z = 8
Monoclinic, P21/cMo Kα radiation
a = 16.827 (2) ŵ = 0.50 mm1
b = 14.1071 (16) ÅT = 293 K
c = 16.760 (4) Å0.50 × 0.43 × 0.13 mm
β = 93.950 (16)°
Data collection top
Enraf-Nonious CAD4
diffractometer
3946 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.028
Tmin = 0.779, Tmax = 0.9363 standard reflections every 300 min
7087 measured reflections intensity decay: none
6845 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0610 restraints
wR(F2) = 0.142H-atom parameters constrained
S = 1.02Δρmax = 0.95 e Å3
6845 reflectionsΔρmin = 0.27 e Å3
481 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*/Ueq
C10.9779 (3)0.8437 (4)0.3458 (3)0.0558 (14)
H1A0.95690.85340.39760.067*
H1B1.03090.87100.34750.067*
C20.9832 (3)0.7395 (4)0.3298 (3)0.0569 (14)
H2A0.99450.72860.27450.068*
H2B1.02570.71150.36400.068*
O30.90958 (18)0.6985 (2)0.34540 (18)0.0503 (9)
C40.9014 (3)0.6031 (3)0.3213 (3)0.0527 (14)
H4A0.94030.56390.35130.063*
H4B0.90960.59700.26480.063*
C50.8184 (3)0.5731 (3)0.3375 (3)0.0544 (14)
H5A0.81090.50680.32340.065*
H5B0.81080.58000.39400.065*
N60.7600 (2)0.6306 (3)0.2911 (2)0.0452 (10)
C70.7144 (3)0.6972 (4)0.3227 (3)0.0529 (14)
S80.66391 (8)0.75875 (11)0.24110 (8)0.0623 (4)
C90.7106 (3)0.6848 (3)0.1758 (3)0.0412 (12)
S100.69014 (8)0.70025 (10)0.07307 (7)0.0559 (4)
C110.7601 (3)0.6182 (3)0.0326 (3)0.0507 (13)
H11A0.75060.55540.05360.061*
H11B0.74970.61550.02500.061*
C120.8464 (3)0.6430 (3)0.0510 (2)0.0402 (12)
C130.8998 (3)0.5740 (4)0.0772 (3)0.0649 (16)
H130.88230.51220.08420.078*
C140.9785 (4)0.5957 (4)0.0930 (4)0.0775 (19)
H141.01440.54850.10980.093*
C151.0049 (3)0.6879 (4)0.0842 (3)0.0651 (16)
H151.05810.70250.09700.078*
C160.9533 (3)0.7575 (3)0.0568 (2)0.0415 (12)
C170.9845 (3)0.8556 (3)0.0443 (3)0.0496 (13)
H17A1.00150.85990.00970.059*
H17B1.03120.86510.08070.059*
S180.91533 (8)0.95059 (9)0.05893 (7)0.0503 (4)
C190.9015 (3)0.9344 (3)0.1604 (3)0.0409 (12)
S200.81373 (9)0.96650 (12)0.20013 (9)0.0764 (5)
C210.8530 (4)0.9240 (4)0.2954 (3)0.0609 (15)
N220.9270 (3)0.8918 (3)0.2847 (2)0.0479 (11)
N230.9545 (2)0.8971 (3)0.2091 (2)0.0467 (10)
N240.7585 (2)0.6232 (3)0.2083 (2)0.0428 (10)
O250.7076 (2)0.7125 (3)0.3933 (2)0.0750 (12)
O260.8193 (3)0.9255 (3)0.3567 (2)0.0982 (15)
C270.8746 (3)0.7340 (3)0.0394 (2)0.0413 (12)
H270.83940.78030.01920.050*
C280.4713 (3)0.8310 (4)0.1179 (3)0.0570 (14)
H28A0.45690.84720.17130.068*
H28B0.52860.83830.11660.068*
C290.4492 (3)0.7300 (4)0.1004 (3)0.0624 (15)
H29A0.45910.71440.04550.075*
H29B0.48080.68790.13560.075*
O300.3676 (2)0.7192 (3)0.1124 (2)0.0624 (10)
C310.3376 (4)0.6275 (4)0.0969 (3)0.0685 (17)
H31A0.35660.58440.13910.082*
H31B0.35510.60420.04650.082*
C320.2481 (3)0.6335 (4)0.0932 (3)0.0639 (16)
H32A0.22540.57060.08600.077*
H32B0.23120.65940.14290.077*
N330.2202 (2)0.6938 (3)0.0269 (2)0.0513 (11)
C340.2022 (3)0.7869 (4)0.0352 (3)0.0506 (13)
S350.18850 (9)0.83401 (10)0.06286 (8)0.0603 (4)
C360.2051 (3)0.7236 (4)0.1019 (3)0.0445 (12)
S370.19962 (8)0.70638 (11)0.20473 (8)0.0589 (4)
C380.27612 (19)0.6185 (2)0.21458 (17)0.0544 (14)
H38A0.26070.56110.18780.065*
H38B0.27860.60370.27090.065*
C390.35807 (19)0.6468 (2)0.18132 (17)0.0472 (13)
C400.40722 (19)0.5802 (2)0.14189 (17)0.0678 (16)
H400.38940.51870.13410.081*
C410.4820 (4)0.6070 (5)0.1149 (4)0.0787 (18)
H410.51520.56210.08910.094*
C420.5109 (3)0.6974 (5)0.1240 (3)0.0677 (17)
H420.56210.71380.10420.081*
C430.4614 (3)0.7636 (4)0.1636 (3)0.0526 (14)
C440.4913 (3)0.8626 (4)0.1757 (3)0.0659 (16)
H44A0.50990.86700.22910.079*
H44B0.53660.87360.13800.079*
S450.41895 (9)0.95576 (10)0.16392 (8)0.0656 (4)
C460.4096 (3)0.9471 (4)0.0612 (3)0.0480 (13)
S470.34723 (8)1.02134 (10)0.01205 (8)0.0576 (4)
C480.3789 (3)0.9635 (4)0.0796 (3)0.0504 (13)
N490.4318 (2)0.8954 (3)0.0607 (2)0.0474 (10)
N500.4498 (2)0.8871 (3)0.0177 (2)0.0472 (10)
N510.2217 (2)0.6583 (3)0.0495 (2)0.0495 (11)
O520.1957 (2)0.8305 (3)0.0971 (2)0.0716 (11)
O530.3582 (2)0.9832 (3)0.1449 (2)0.0656 (10)
C540.3866 (3)0.7372 (4)0.1920 (3)0.0477 (13)
H540.35400.78150.21920.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.059 (3)0.067 (4)0.040 (3)0.016 (3)0.002 (3)0.011 (3)
C20.048 (3)0.064 (4)0.058 (3)0.000 (3)0.006 (3)0.015 (3)
O30.046 (2)0.046 (2)0.059 (2)0.0066 (17)0.0049 (17)0.0053 (17)
C40.063 (4)0.039 (3)0.055 (3)0.010 (3)0.007 (3)0.001 (3)
C50.073 (4)0.043 (3)0.044 (3)0.013 (3)0.017 (3)0.010 (2)
N60.049 (3)0.053 (3)0.032 (2)0.013 (2)0.0006 (19)0.006 (2)
C70.046 (3)0.076 (4)0.037 (3)0.008 (3)0.008 (2)0.002 (3)
S80.0586 (9)0.0836 (11)0.0453 (8)0.0157 (8)0.0077 (7)0.0027 (7)
C90.040 (3)0.049 (3)0.035 (3)0.008 (2)0.004 (2)0.002 (2)
S100.0572 (8)0.0766 (10)0.0335 (7)0.0077 (8)0.0004 (6)0.0090 (7)
C110.061 (3)0.057 (3)0.034 (3)0.009 (3)0.005 (2)0.002 (2)
C120.051 (3)0.044 (3)0.026 (2)0.003 (3)0.009 (2)0.003 (2)
C130.069 (4)0.040 (3)0.088 (4)0.002 (3)0.020 (3)0.007 (3)
C140.067 (4)0.044 (4)0.121 (6)0.012 (3)0.008 (4)0.025 (4)
C150.051 (3)0.062 (4)0.083 (4)0.002 (3)0.009 (3)0.010 (3)
C160.054 (3)0.041 (3)0.031 (3)0.005 (3)0.013 (2)0.001 (2)
C170.064 (3)0.047 (3)0.040 (3)0.002 (3)0.017 (2)0.002 (2)
S180.0730 (9)0.0403 (7)0.0388 (7)0.0019 (7)0.0124 (6)0.0069 (6)
C190.048 (3)0.035 (3)0.041 (3)0.005 (2)0.011 (2)0.002 (2)
S200.0772 (11)0.0910 (12)0.0645 (10)0.0343 (9)0.0289 (8)0.0283 (9)
C210.085 (4)0.050 (4)0.051 (3)0.017 (3)0.027 (3)0.004 (3)
N220.069 (3)0.042 (3)0.033 (2)0.005 (2)0.003 (2)0.0022 (19)
N230.052 (3)0.053 (3)0.036 (2)0.004 (2)0.011 (2)0.000 (2)
N240.052 (3)0.048 (3)0.028 (2)0.006 (2)0.0004 (18)0.0014 (19)
O250.076 (3)0.112 (3)0.037 (2)0.002 (2)0.0075 (19)0.009 (2)
O260.141 (4)0.096 (3)0.065 (3)0.045 (3)0.062 (3)0.018 (2)
C270.057 (3)0.037 (3)0.031 (3)0.009 (3)0.009 (2)0.005 (2)
C280.060 (4)0.067 (4)0.043 (3)0.001 (3)0.004 (3)0.004 (3)
C290.070 (4)0.067 (4)0.050 (3)0.014 (3)0.003 (3)0.009 (3)
O300.076 (3)0.055 (2)0.056 (2)0.004 (2)0.007 (2)0.0089 (18)
C310.104 (5)0.049 (4)0.052 (3)0.005 (4)0.006 (3)0.006 (3)
C320.093 (5)0.057 (4)0.043 (3)0.019 (3)0.014 (3)0.007 (3)
N330.069 (3)0.048 (3)0.037 (2)0.007 (2)0.008 (2)0.005 (2)
C340.047 (3)0.059 (4)0.045 (3)0.002 (3)0.006 (2)0.010 (3)
S350.0699 (10)0.0512 (9)0.0586 (9)0.0087 (8)0.0046 (7)0.0067 (7)
C360.037 (3)0.055 (3)0.041 (3)0.012 (3)0.004 (2)0.003 (3)
S370.0575 (9)0.0796 (10)0.0396 (7)0.0021 (8)0.0028 (6)0.0057 (7)
C380.061 (4)0.059 (3)0.045 (3)0.015 (3)0.014 (3)0.016 (3)
C390.056 (3)0.050 (3)0.037 (3)0.002 (3)0.011 (2)0.011 (2)
C400.070 (4)0.065 (4)0.070 (4)0.001 (3)0.020 (3)0.005 (3)
C410.079 (5)0.074 (5)0.084 (5)0.015 (4)0.009 (4)0.003 (4)
C420.045 (3)0.098 (5)0.061 (4)0.001 (4)0.009 (3)0.014 (4)
C430.056 (4)0.061 (4)0.041 (3)0.008 (3)0.010 (3)0.016 (3)
C440.071 (4)0.080 (4)0.048 (3)0.018 (3)0.020 (3)0.018 (3)
S450.0924 (11)0.0623 (10)0.0416 (8)0.0188 (9)0.0023 (7)0.0044 (7)
C460.048 (3)0.052 (3)0.044 (3)0.011 (3)0.003 (2)0.002 (3)
S470.0565 (9)0.0534 (9)0.0629 (9)0.0022 (7)0.0037 (7)0.0059 (7)
C480.048 (3)0.050 (3)0.053 (3)0.015 (3)0.007 (3)0.001 (3)
N490.050 (3)0.052 (3)0.040 (2)0.005 (2)0.004 (2)0.000 (2)
N500.048 (3)0.057 (3)0.037 (2)0.003 (2)0.0082 (19)0.001 (2)
N510.062 (3)0.048 (3)0.040 (2)0.008 (2)0.011 (2)0.011 (2)
O520.081 (3)0.076 (3)0.058 (2)0.006 (2)0.006 (2)0.032 (2)
O530.073 (3)0.070 (3)0.057 (2)0.002 (2)0.027 (2)0.006 (2)
C540.056 (3)0.053 (3)0.035 (3)0.004 (3)0.011 (2)0.005 (2)
Geometric parameters (Å, º) top
C1—N221.456 (6)C28—N491.449 (6)
C1—C21.497 (7)C28—C291.498 (7)
C1—H1A0.9700C28—H28A0.9700
C1—H1B0.9700C28—H28B0.9700
C2—O31.409 (5)C29—O301.411 (6)
C2—H2A0.9700C29—H29A0.9700
C2—H2B0.9700C29—H29B0.9700
O3—C41.409 (5)O30—C311.407 (6)
C4—C51.501 (6)C31—C321.505 (7)
C4—H4A0.9700C31—H31A0.9700
C4—H4B0.9700C31—H31B0.9700
C5—N61.458 (5)C32—N331.450 (6)
C5—H5A0.9700C32—H32A0.9700
C5—H5B0.9700C32—H32B0.9700
N6—C71.344 (6)N33—C341.357 (6)
N6—N241.390 (5)N33—N511.376 (5)
C7—O251.216 (5)C34—O521.218 (5)
C7—S81.785 (5)C34—S351.773 (5)
S8—C91.738 (5)S35—C361.720 (5)
C9—N241.281 (5)C36—N511.290 (6)
C9—S101.746 (5)C36—S371.736 (5)
S10—C111.815 (5)S37—C381.803 (4)
C11—C121.504 (6)C38—C391.5049
C11—H11A0.9700C38—H38A0.9700
C11—H11B0.9700C38—H38B0.9700
C12—C131.376 (6)C39—C541.379 (5)
C12—C271.388 (6)C39—C401.3882
C13—C141.366 (7)C40—C411.362 (7)
C13—H130.9300C40—H400.9300
C14—C151.384 (7)C41—C421.378 (8)
C14—H140.9300C41—H410.9300
C15—C161.369 (6)C42—C431.389 (7)
C15—H150.9300C42—H420.9300
C16—C271.377 (6)C43—C541.367 (6)
C16—C171.500 (6)C43—C441.503 (7)
C17—S181.802 (5)C44—S451.811 (5)
C17—H17A0.9700C44—H44A0.9700
C17—H17B0.9700C44—H44B0.9700
S18—C191.747 (5)S45—C461.743 (5)
C19—N231.279 (5)C46—N501.280 (6)
C19—S201.723 (5)C46—S471.731 (5)
S20—C211.790 (5)S47—C481.788 (5)
C21—O261.207 (5)C48—O531.203 (5)
C21—N221.349 (6)C48—N491.361 (6)
N22—N231.382 (5)N49—N501.375 (5)
C27—H270.9300C54—H540.9300
N22—C1—C2111.8 (4)N49—C28—C29111.7 (4)
N22—C1—H1A109.2N49—C28—H28A109.3
C2—C1—H1A109.2C29—C28—H28A109.3
N22—C1—H1B109.2N49—C28—H28B109.3
C2—C1—H1B109.2C29—C28—H28B109.3
H1A—C1—H1B107.9H28A—C28—H28B107.9
O3—C2—C1107.8 (4)O30—C29—C28107.8 (4)
O3—C2—H2A110.1O30—C29—H29A110.1
C1—C2—H2A110.1C28—C29—H29A110.1
O3—C2—H2B110.1O30—C29—H29B110.1
C1—C2—H2B110.1C28—C29—H29B110.1
H2A—C2—H2B108.5H29A—C29—H29B108.5
C4—O3—C2114.1 (4)C31—O30—C29114.4 (4)
O3—C4—C5106.9 (4)O30—C31—C32107.5 (5)
O3—C4—H4A110.3O30—C31—H31A110.2
C5—C4—H4A110.3C32—C31—H31A110.2
O3—C4—H4B110.3O30—C31—H31B110.2
C5—C4—H4B110.3C32—C31—H31B110.2
H4A—C4—H4B108.6H31A—C31—H31B108.5
N6—C5—C4110.3 (4)N33—C32—C31109.6 (4)
N6—C5—H5A109.6N33—C32—H32A109.8
C4—C5—H5A109.6C31—C32—H32A109.8
N6—C5—H5B109.6N33—C32—H32B109.8
C4—C5—H5B109.6C31—C32—H32B109.8
H5A—C5—H5B108.1H32A—C32—H32B108.2
C7—N6—N24118.3 (4)C34—N33—N51117.7 (4)
C7—N6—C5124.1 (4)C34—N33—C32123.5 (4)
N24—N6—C5117.2 (4)N51—N33—C32118.2 (4)
O25—C7—N6127.0 (5)O52—C34—N33127.6 (5)
O25—C7—S8125.9 (5)O52—C34—S35125.9 (4)
N6—C7—S8107.0 (3)N33—C34—S35106.5 (4)
C9—S8—C788.7 (2)C36—S35—C3489.9 (2)
N24—C9—S8116.0 (3)N51—C36—S35114.9 (3)
N24—C9—S10125.4 (4)N51—C36—S37124.8 (4)
S8—C9—S10118.6 (3)S35—C36—S37120.3 (3)
C9—S10—C11101.5 (2)C36—S37—C38101.4 (2)
C12—C11—S10114.7 (3)C39—C38—S37115.22 (11)
C12—C11—H11A108.6C39—C38—H38A108.5
S10—C11—H11A108.6S37—C38—H38A108.5
C12—C11—H11B108.6C39—C38—H38B108.5
S10—C11—H11B108.6S37—C38—H38B108.5
H11A—C11—H11B107.6H38A—C38—H38B107.5
C13—C12—C27118.4 (5)C54—C39—C40119.1 (3)
C13—C12—C11120.1 (5)C54—C39—C38121.0 (3)
C27—C12—C11121.4 (4)C40—C39—C38119.9
C14—C13—C12120.5 (5)C41—C40—C39118.5 (3)
C14—C13—H13119.8C41—C40—H40120.8
C12—C13—H13119.8C39—C40—H40120.8
C13—C14—C15120.2 (5)C40—C41—C42123.1 (6)
C13—C14—H14119.9C40—C41—H41118.5
C15—C14—H14119.9C42—C41—H41118.5
C16—C15—C14120.6 (5)C41—C42—C43118.1 (5)
C16—C15—H15119.7C41—C42—H42120.9
C14—C15—H15119.7C43—C42—H42120.9
C15—C16—C27118.4 (5)C54—C43—C42119.4 (5)
C15—C16—C17119.3 (5)C54—C43—C44121.0 (5)
C27—C16—C17122.2 (4)C42—C43—C44119.6 (5)
C16—C17—S18115.6 (3)C43—C44—S45115.2 (4)
C16—C17—H17A108.4C43—C44—H44A108.5
S18—C17—H17A108.4S45—C44—H44A108.5
C16—C17—H17B108.4C43—C44—H44B108.5
S18—C17—H17B108.4S45—C44—H44B108.5
H17A—C17—H17B107.5H44A—C44—H44B107.5
C19—S18—C1799.5 (2)C46—S45—C4499.4 (2)
N23—C19—S20116.1 (3)N50—C46—S47116.3 (4)
N23—C19—S18122.8 (4)N50—C46—S45121.9 (4)
S20—C19—S18121.1 (3)S47—C46—S45121.8 (3)
C19—S20—C2189.0 (2)C46—S47—C4888.8 (2)
O26—C21—N22127.7 (5)O53—C48—N49127.5 (5)
O26—C21—S20125.9 (5)O53—C48—S47126.0 (4)
N22—C21—S20106.4 (4)N49—C48—S47106.4 (4)
C21—N22—N23118.3 (4)C48—N49—N50118.3 (4)
C21—N22—C1124.6 (4)C48—N49—C28124.5 (4)
N23—N22—C1116.9 (4)N50—N49—C28117.2 (4)
C19—N23—N22110.2 (4)C46—N50—N49110.2 (4)
C9—N24—N6109.9 (4)C36—N51—N33110.9 (4)
C16—C27—C12121.8 (4)C43—C54—C39121.8 (5)
C16—C27—H27119.1C43—C54—H54119.1
C12—C27—H27119.1C39—C54—H54119.1
N22—C1—C2—O372.0 (5)N49—C28—C29—O3066.1 (5)
C1—C2—O3—C4170.8 (4)C28—C29—O30—C31179.0 (4)
C2—O3—C4—C5176.5 (4)C29—O30—C31—C32166.6 (4)
O3—C4—C5—N661.3 (5)O30—C31—C32—N3363.2 (5)
C4—C5—N6—C7108.2 (5)C31—C32—N33—C3497.0 (6)
C4—C5—N6—N2464.2 (5)C31—C32—N33—N5174.5 (5)
N24—N6—C7—O25178.7 (5)N51—N33—C34—O52177.7 (5)
C5—N6—C7—O259.0 (8)C32—N33—C34—O5210.8 (8)
N24—N6—C7—S80.5 (5)N51—N33—C34—S351.6 (5)
C5—N6—C7—S8171.8 (3)C32—N33—C34—S35169.9 (4)
O25—C7—S8—C9178.5 (5)O52—C34—S35—C36177.5 (5)
N6—C7—S8—C90.7 (3)N33—C34—S35—C361.9 (4)
C7—S8—C9—N241.0 (4)C34—S35—C36—N511.9 (4)
C7—S8—C9—S10179.6 (3)C34—S35—C36—S37178.4 (3)
N24—C9—S10—C115.6 (5)N51—C36—S37—C3834.6 (4)
S8—C9—S10—C11173.7 (3)S35—C36—S37—C38145.1 (3)
C9—S10—C11—C1264.9 (4)C36—S37—C38—C3957.73 (18)
S10—C11—C12—C13134.3 (4)S37—C38—C39—C5440.8 (2)
S10—C11—C12—C2748.2 (5)S37—C38—C39—C40141.63 (11)
C27—C12—C13—C141.5 (8)C54—C39—C40—C410.2 (3)
C11—C12—C13—C14179.1 (5)C38—C39—C40—C41177.7 (3)
C12—C13—C14—C151.1 (9)C39—C40—C41—C420.9 (7)
C13—C14—C15—C162.4 (9)C40—C41—C42—C431.0 (8)
C14—C15—C16—C270.8 (8)C41—C42—C43—C540.0 (8)
C14—C15—C16—C17177.2 (5)C41—C42—C43—C44179.1 (5)
C15—C16—C17—S18149.4 (4)C54—C43—C44—S4540.0 (6)
C27—C16—C17—S1832.6 (6)C42—C43—C44—S45140.8 (4)
C16—C17—S18—C1963.3 (4)C43—C44—S45—C4668.8 (4)
C17—S18—C19—N2327.4 (4)C44—S45—C46—N501.1 (5)
C17—S18—C19—S20151.5 (3)C44—S45—C46—S47179.3 (3)
N23—C19—S20—C210.1 (4)N50—C46—S47—C480.5 (4)
S18—C19—S20—C21178.8 (3)S45—C46—S47—C48178.8 (3)
C19—S20—C21—O26179.5 (6)C46—S47—C48—O53178.0 (5)
C19—S20—C21—N220.3 (4)C46—S47—C48—N490.4 (3)
O26—C21—N22—N23179.7 (5)O53—C48—N49—N50177.1 (5)
S20—C21—N22—N230.5 (5)S47—C48—N49—N501.3 (5)
O26—C21—N22—C16.2 (9)O53—C48—N49—C282.3 (8)
S20—C21—N22—C1174.6 (4)S47—C48—N49—C28179.3 (4)
C2—C1—N22—C21106.0 (6)C29—C28—N49—C48117.2 (5)
C2—C1—N22—N2368.2 (5)C29—C28—N49—N5063.4 (6)
S20—C19—N23—N220.1 (5)S47—C46—N50—N491.2 (5)
S18—C19—N23—N22179.1 (3)S45—C46—N50—N49179.5 (3)
C21—N22—N23—C190.4 (6)C48—N49—N50—C461.6 (6)
C1—N22—N23—C19175.0 (4)C28—N49—N50—C46178.9 (4)
S8—C9—N24—N60.9 (5)S35—C36—N51—N331.3 (5)
S10—C9—N24—N6179.8 (3)S37—C36—N51—N33179.0 (3)
C7—N6—N24—C90.3 (5)C34—N33—N51—C360.3 (6)
C5—N6—N24—C9173.1 (4)C32—N33—N51—C36171.7 (4)
C15—C16—C27—C121.9 (7)C42—C43—C54—C391.0 (7)
C17—C16—C27—C12179.9 (4)C44—C43—C54—C39179.9 (4)
C13—C12—C27—C163.1 (7)C40—C39—C54—C431.1 (5)
C11—C12—C27—C16179.3 (4)C38—C39—C54—C43178.6 (3)

Experimental details

Crystal data
Chemical formulaC16H16N4O3S4
Mr440.57
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)16.827 (2), 14.1071 (16), 16.760 (4)
β (°) 93.950 (16)
V3)3969.0 (12)
Z8
Radiation typeMo Kα
µ (mm1)0.50
Crystal size (mm)0.50 × 0.43 × 0.13
Data collection
DiffractometerEnraf-Nonious CAD4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.779, 0.936
No. of measured, independent and
observed [I > 2σ(I)] reflections
7087, 6845, 3946
Rint0.028
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.142, 1.02
No. of reflections6845
No. of parameters481
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.95, 0.27

Computer programs: CAD-4 EXPRESS (Enraf-Nonious, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top
C7—O251.216 (5)C34—O521.218 (5)
C7—S81.785 (5)C34—S351.773 (5)
S8—C91.738 (5)S35—C361.720 (5)
C9—S101.746 (5)C36—S371.736 (5)
S10—C111.815 (5)S37—C381.803 (4)
C17—S181.802 (5)C44—S451.811 (5)
S18—C191.747 (5)S45—C461.743 (5)
C19—S201.723 (5)C46—S471.731 (5)
S20—C211.790 (5)S47—C481.788 (5)
C21—O261.207 (5)C48—O531.203 (5)
C9—S8—C788.7 (2)C36—S35—C3489.9 (2)
C19—S20—C2189.0 (2)C46—S47—C4888.8 (2)
 

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