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ISSN: 2056-9890

(4R,11R)-9-(1-hydroxypropan-2-yl)-4,11-di­phenyl-1,3,5,7,9-penta­azatri­cyclo[5.3.1.04,11]undecane-2,6-di­thione

aKey Laboratory of Pesticide and Chemical Biology of the Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
*Correspondence e-mail: wangmeng8511@163.com

(Received 2 June 2011; accepted 7 July 2011; online 16 July 2011)

The asymmetric unit of the title compound, C21H23N5OS2, contains two independent chiral mol­ecules. The two phenyl rings of one mol­ecule form a dihedral angle of 51.95 (7)° and the distance between their centroids is 4.345 (1) Å. In the other mol­ecule, the phenyl rings form a dihedral angle of 58.79 (8)° with a ring centroid–centroid distance of 4.435 (2) Å. An intra­molecular O—H⋯N hydrogen bond occurs in each independent mol­ecule. The crystal packing is stabilized by and inter­molecular N—H⋯O and N—H⋯S hydrogen bonds and C—H⋯S inter­actions.

Related literature

For crystal engineering studies of similar compounds, see: Deng et al. (2010[Deng, C., Shu, W. & Zhang, D. (2010). Acta Cryst. E66, o1524.]); Wang & Xi (2009[Wang, Z. & Xi, H. (2009). Acta Cryst. E65, o1426.]). For the preparation of the title compound, see: Cao et al. (2010[Cao, L.-P., Meng, X.-G., Ding, J.-Y., Chen, Y.-F., Gao, M., Wu, Y.-D., Li, I.-T., Wu, A.-X. & Isaacs, L. (2010). Chem. Commun. 46, 4508-4510.]); Li et al. (2008[Li, Y., Meng, X., Cao, L. & Wu, A. (2008). Cryst. Growth Des. 8, 1645-1653.]).

[Scheme 1]

Experimental

Crystal data
  • C21H23N5OS2

  • Mr = 425.58

  • Monoclinic, P 21

  • a = 9.0030 (9) Å

  • b = 12.6382 (13) Å

  • c = 18.5830 (2) Å

  • β = 100.169 (2)°

  • V = 2081.2 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.28 mm−1

  • T = 298 K

  • 0.25 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART 4K CCD area-detector diffractometer

  • 14076 measured reflections

  • 9634 independent reflections

  • 8871 reflections with I > 2σ(I)

  • Rint = 0.020

Refinement
  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 0.133

  • S = 1.08

  • 9634 reflections

  • 543 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.39 e Å−3

  • Δρmin = −0.25 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 4300 Friedel pairs

  • Flack parameter: 0.04 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N10—H10A⋯S3i 0.76 (4) 2.86 (4) 3.584 (3) 160 (3)
N9—H9A⋯S4ii 0.85 (4) 2.79 (4) 3.542 (3) 148 (3)
N9—H9A⋯O2iii 0.85 (4) 2.36 (4) 2.913 (3) 124 (3)
N5—H5A⋯S1iv 0.79 (4) 2.63 (4) 3.400 (2) 169 (3)
N4—H4A⋯O1iii 0.83 (3) 2.39 (3) 2.940 (3) 124 (3)
C22—H22B⋯S4v 0.97 2.85 3.578 (3) 132
C20—H20B⋯S1vi 0.97 2.85 3.548 (3) 129
O1—H1⋯N1 0.96 (4) 2.04 (3) 2.685 (3) 123 (3)
O2—H2⋯N6 0.97 (4) 1.95 (4) 2.682 (3) 130 (3)
Symmetry codes: (i) [-x+2, y+{\script{1\over 2}}, -z+2]; (ii) [-x+2, y-{\script{1\over 2}}, -z+2]; (iii) x+1, y, z; (iv) [-x+1, y+{\script{1\over 2}}, -z+1]; (v) [-x+1, y-{\script{1\over 2}}, -z+2]; (vi) [-x, y+{\script{1\over 2}}, -z+1].

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON, SHELXL97 and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

Glycoluril derivatives have been applied in many fields, including explosives and as slow-release fertilizers. The title compound was synthesized as part of our extensive research on derivatives of glycoluril. The molecular structure is shown in Fig. 1. The triazine six-membered ring displays a normal chair conformation. In the crystal structure, intramolecular O—H···N and intermolecular N—H···O hydrogen bonds as well as weak intermolecular N—H···S hydrogen bonds help to establish the packing.

Related literature top

For crystal engineering studies of similar compounds, see: Deng et al. (2010); Wang & Xi (2009). For the preparation of the title compound, see: Cao et al. (2010); Li et al. (2008).

Experimental top

The title compound was synthesized according to the reported literature (Li et al., 2008). Crystals of the title compound suitable for X-ray diffraction were grown by slow evaporation of a dichloromethane-methanol (4:1) solution of the title compound at 293 K.

Refinement top

All H atoms bound to carbon were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.98 Å and Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(CMe). All H-atoms bound to nitrogen were found in difference maps and then placed at ideal positions with the N—H = 0.87Å and Uiso(H) = 1.2Ueq(N). Hydroxyl H-atoms were found in difference maps and refined with Uiso(H) = 1.5Ueq(O).

The structure is chiral, and the Flack parameter refines to a satisfactory value of x = 0.04 (6). Nevertheless, tests using Platon (Spek, 2009) suggest transformation to space group P21/c. This possibility was tested, but it gave a disordered model that was clearly flawed.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and pubCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. showing the asymmetric unit, with displacement ellipsoids drawn at the 30% probability level.
(4R,11R)-9-(1-hydroxypropan-2-yl)-4,11-diphenyl-1,3,5,7,9- pentaazatricyclo[5.3.1.04,11]undecane-2,6-dithione top
Crystal data top
C21H23N5OS2F(000) = 896
Mr = 425.58Dx = 1.358 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 4930 reflections
a = 9.0030 (9) Åθ = 0.0–0.0°
b = 12.6382 (13) ŵ = 0.28 mm1
c = 18.5830 (2) ÅT = 298 K
β = 100.169 (2)°Block, colorless
V = 2081.2 (4) Å30.25 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
8871 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.020
Graphite monochromatorθmax = 28.3°, θmin = 2.0°
ϕ and ω scansh = 911
14076 measured reflectionsk = 1616
9634 independent reflectionsl = 2422
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.133 w = 1/[σ2(Fo2) + (0.0728P)2 + 0.1223P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
9634 reflectionsΔρmax = 0.39 e Å3
543 parametersΔρmin = 0.25 e Å3
1 restraintAbsolute structure: Flack (1983), 4300 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.04 (6)
Crystal data top
C21H23N5OS2V = 2081.2 (4) Å3
Mr = 425.58Z = 4
Monoclinic, P21Mo Kα radiation
a = 9.0030 (9) ŵ = 0.28 mm1
b = 12.6382 (13) ÅT = 298 K
c = 18.5830 (2) Å0.25 × 0.20 × 0.20 mm
β = 100.169 (2)°
Data collection top
Bruker SMART 4K CCD area-detector
diffractometer
8871 reflections with I > 2σ(I)
14076 measured reflectionsRint = 0.020
9634 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.055H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.133Δρmax = 0.39 e Å3
S = 1.08Δρmin = 0.25 e Å3
9634 reflectionsAbsolute structure: Flack (1983), 4300 Friedel pairs
543 parametersAbsolute structure parameter: 0.04 (6)
1 restraint
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
C10.0087 (3)0.7199 (2)0.40140 (14)0.0327 (5)
H1A0.05240.74470.35630.039*
H1B0.01580.64610.40750.039*
C20.0195 (3)0.8891 (2)0.46139 (15)0.0333 (6)
H2A0.00630.92310.50670.040*
H2B0.04270.92630.42140.040*
C30.2791 (3)0.6653 (2)0.43454 (15)0.0333 (6)
C40.2955 (3)0.9396 (2)0.49851 (14)0.0318 (6)
C50.2239 (3)0.8369 (2)0.39335 (13)0.0279 (5)
C60.1707 (3)0.8900 (2)0.31971 (14)0.0323 (6)
C70.1547 (4)0.8312 (3)0.25592 (15)0.0458 (7)
H70.17560.75910.25770.055*
C80.1069 (4)0.8815 (3)0.18885 (18)0.0597 (10)
H80.09780.84260.14580.072*
C90.0734 (4)0.9867 (3)0.18586 (19)0.0608 (10)
H90.04031.01900.14090.073*
C100.0885 (4)1.0451 (3)0.24900 (19)0.0576 (9)
H100.06531.11680.24680.069*
C110.1385 (4)0.9968 (3)0.31635 (16)0.0449 (7)
H110.15031.03670.35910.054*
C120.4004 (3)0.8274 (2)0.42058 (14)0.0298 (5)
C130.5006 (3)0.8395 (2)0.36367 (15)0.0356 (6)
C140.5248 (4)0.7536 (3)0.3207 (2)0.0571 (9)
H140.47990.68890.32730.069*
C150.6163 (5)0.7638 (4)0.2678 (2)0.0754 (13)
H150.62950.70640.23820.090*
C160.6858 (5)0.8568 (5)0.2592 (2)0.0794 (15)
H160.74840.86270.22460.095*
C170.6640 (4)0.9408 (4)0.3010 (2)0.0708 (12)
H170.71201.00450.29480.085*
C180.5709 (4)0.9339 (3)0.35345 (18)0.0513 (8)
H180.55630.99270.38140.062*
C190.0175 (3)0.7270 (2)0.53353 (14)0.0348 (5)
H190.03730.65160.52400.042*
C200.1461 (3)0.7702 (3)0.56985 (17)0.0453 (7)
H20A0.15930.72460.61020.054*
H20B0.11950.84030.58930.054*
C210.1319 (3)0.7357 (3)0.58612 (16)0.0485 (8)
H21A0.21120.70710.56350.073*
H21B0.12620.69680.62990.073*
H21C0.15280.80870.59810.073*
C220.5347 (3)0.8098 (2)0.95706 (14)0.0305 (5)
H22A0.47530.78250.91220.037*
H22B0.52290.76160.99630.037*
C230.5052 (3)0.9915 (2)0.91961 (14)0.0307 (5)
H23A0.47901.06090.93580.037*
H23B0.44070.97710.87310.037*
C240.8133 (3)0.7917 (2)1.00265 (13)0.0301 (5)
C250.7688 (3)1.0667 (2)0.93261 (14)0.0322 (6)
C260.7301 (3)0.89034 (19)0.89609 (13)0.0267 (5)
C270.6763 (3)0.8523 (2)0.81857 (14)0.0321 (6)
C280.6589 (4)0.7455 (3)0.80296 (17)0.0485 (8)
H280.68440.69580.84000.058*
C290.6036 (4)0.7124 (4)0.7324 (2)0.0682 (11)
H290.58890.64060.72260.082*
C300.5708 (4)0.7836 (5)0.67732 (19)0.0745 (14)
H300.53340.76060.63000.089*
C310.5924 (4)0.8889 (5)0.6912 (2)0.0729 (13)
H310.57330.93730.65290.088*
C320.6426 (4)0.9244 (3)0.76170 (17)0.0530 (8)
H320.65370.99660.77100.064*
C330.9044 (3)0.9102 (2)0.92241 (13)0.0291 (5)
C341.0088 (3)0.8872 (2)0.86789 (14)0.0327 (6)
C351.0333 (4)0.9641 (3)0.81817 (19)0.0567 (9)
H350.98541.02940.81750.068*
C361.1301 (5)0.9430 (5)0.7692 (2)0.0803 (14)
H361.14590.99460.73560.096*
C371.2020 (4)0.8481 (5)0.7696 (2)0.0774 (15)
H371.26730.83510.73700.093*
C381.1775 (4)0.7728 (4)0.8180 (2)0.0696 (12)
H381.22710.70810.81870.084*
C391.0797 (3)0.7906 (3)0.86668 (17)0.0478 (8)
H391.06190.73720.89860.057*
C400.4939 (3)0.9423 (2)1.05056 (14)0.0325 (5)
H400.49410.87651.07850.039*
C410.3536 (3)1.0042 (2)1.06007 (16)0.0413 (6)
H41A0.34741.00791.11160.050*
H41B0.36091.07591.04240.050*
C420.6351 (3)1.0042 (3)1.08372 (16)0.0441 (7)
H42A0.72280.96131.08300.066*
H42B0.62971.02291.13330.066*
H42C0.64171.06731.05570.066*
N10.0297 (2)0.78024 (17)0.46192 (12)0.0315 (5)
N20.1697 (2)0.72850 (18)0.39543 (12)0.0309 (5)
N30.1782 (2)0.89701 (18)0.45329 (11)0.0290 (4)
N40.4072 (2)0.7193 (2)0.45007 (13)0.0364 (5)
H4A0.486 (4)0.688 (3)0.4681 (16)0.044*
N50.4231 (3)0.9080 (2)0.47628 (13)0.0381 (5)
H5A0.503 (4)0.930 (3)0.4934 (18)0.046*
N60.4774 (2)0.91310 (17)0.97243 (11)0.0294 (4)
N70.6935 (2)0.81281 (17)0.94950 (11)0.0261 (4)
N80.6638 (2)0.99257 (17)0.90927 (11)0.0289 (4)
N90.9352 (3)0.8419 (2)0.98643 (13)0.0365 (5)
H9A1.022 (4)0.832 (3)1.0115 (17)0.044*
N100.9063 (3)1.0212 (2)0.94075 (14)0.0400 (6)
H10A0.979 (4)1.054 (3)0.9465 (17)0.048*
O10.2835 (3)0.7757 (2)0.51903 (15)0.0607 (7)
H10.251 (5)0.777 (4)0.472 (2)0.091*
O20.2204 (2)0.9554 (2)1.02108 (13)0.0496 (6)
H20.268 (4)0.916 (4)0.986 (2)0.074*
S10.25277 (9)0.53965 (6)0.45623 (5)0.0503 (2)
S20.28553 (9)1.02021 (7)0.56882 (4)0.0469 (2)
S30.80953 (8)0.71417 (6)1.07516 (4)0.04121 (18)
S40.73491 (9)1.19461 (6)0.94594 (5)0.0468 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0237 (11)0.0382 (14)0.0364 (12)0.0003 (10)0.0058 (9)0.0016 (11)
C20.0213 (11)0.0389 (15)0.0402 (14)0.0049 (10)0.0067 (10)0.0013 (11)
C30.0262 (13)0.0354 (15)0.0410 (14)0.0021 (10)0.0132 (11)0.0025 (11)
C40.0285 (13)0.0339 (14)0.0320 (13)0.0017 (11)0.0023 (10)0.0015 (11)
C50.0219 (12)0.0319 (13)0.0299 (12)0.0027 (10)0.0050 (9)0.0006 (10)
C60.0244 (12)0.0401 (15)0.0324 (13)0.0002 (11)0.0046 (10)0.0038 (11)
C70.0526 (19)0.0477 (18)0.0370 (15)0.0008 (14)0.0069 (13)0.0048 (13)
C80.064 (2)0.081 (3)0.0331 (16)0.009 (2)0.0039 (14)0.0026 (16)
C90.057 (2)0.078 (3)0.0445 (18)0.0003 (18)0.0005 (15)0.0271 (18)
C100.063 (2)0.053 (2)0.057 (2)0.0086 (17)0.0097 (16)0.0232 (16)
C110.0550 (19)0.0402 (16)0.0396 (15)0.0030 (14)0.0084 (13)0.0057 (13)
C120.0220 (12)0.0331 (14)0.0345 (13)0.0007 (10)0.0055 (10)0.0016 (11)
C130.0243 (13)0.0454 (16)0.0373 (14)0.0052 (11)0.0060 (10)0.0075 (12)
C140.062 (2)0.053 (2)0.062 (2)0.0128 (17)0.0286 (17)0.0003 (16)
C150.086 (3)0.090 (3)0.060 (2)0.037 (3)0.040 (2)0.011 (2)
C160.059 (2)0.123 (4)0.066 (2)0.031 (3)0.037 (2)0.033 (3)
C170.056 (2)0.095 (3)0.065 (2)0.014 (2)0.0196 (18)0.032 (2)
C180.0465 (18)0.058 (2)0.0504 (18)0.0086 (16)0.0096 (14)0.0089 (16)
C190.0312 (13)0.0379 (14)0.0365 (13)0.0016 (11)0.0089 (10)0.0043 (11)
C200.0392 (16)0.0513 (18)0.0495 (17)0.0029 (13)0.0195 (13)0.0062 (14)
C210.0392 (16)0.067 (2)0.0381 (15)0.0068 (15)0.0028 (12)0.0070 (15)
C220.0243 (12)0.0340 (13)0.0342 (12)0.0037 (10)0.0074 (10)0.0021 (11)
C230.0208 (11)0.0350 (14)0.0365 (13)0.0016 (10)0.0059 (10)0.0015 (11)
C240.0264 (12)0.0338 (14)0.0308 (12)0.0015 (10)0.0071 (10)0.0016 (10)
C250.0328 (13)0.0297 (14)0.0371 (14)0.0020 (10)0.0142 (11)0.0020 (11)
C260.0236 (11)0.0234 (12)0.0336 (12)0.0012 (9)0.0061 (9)0.0018 (10)
C270.0231 (12)0.0461 (16)0.0268 (12)0.0005 (11)0.0038 (9)0.0005 (11)
C280.0526 (19)0.0499 (19)0.0420 (16)0.0008 (15)0.0052 (13)0.0103 (13)
C290.060 (2)0.088 (3)0.057 (2)0.010 (2)0.0114 (17)0.035 (2)
C300.045 (2)0.143 (5)0.0352 (17)0.002 (2)0.0056 (14)0.027 (2)
C310.053 (2)0.125 (4)0.0385 (18)0.014 (2)0.0035 (15)0.019 (2)
C320.0459 (17)0.070 (2)0.0423 (16)0.0030 (17)0.0054 (13)0.0070 (16)
C330.0222 (11)0.0346 (14)0.0314 (12)0.0043 (10)0.0073 (9)0.0030 (11)
C340.0208 (12)0.0446 (16)0.0340 (13)0.0043 (11)0.0082 (10)0.0060 (11)
C350.058 (2)0.063 (2)0.055 (2)0.0059 (17)0.0263 (16)0.0022 (17)
C360.075 (3)0.119 (4)0.055 (2)0.030 (3)0.034 (2)0.002 (2)
C370.045 (2)0.137 (5)0.055 (2)0.012 (2)0.0228 (17)0.041 (3)
C380.044 (2)0.098 (3)0.066 (2)0.018 (2)0.0060 (17)0.041 (2)
C390.0399 (16)0.055 (2)0.0485 (17)0.0098 (14)0.0079 (13)0.0149 (15)
C400.0260 (12)0.0378 (14)0.0346 (13)0.0026 (10)0.0077 (10)0.0012 (11)
C410.0382 (15)0.0424 (16)0.0463 (15)0.0026 (12)0.0156 (12)0.0068 (13)
C420.0358 (15)0.0544 (18)0.0406 (14)0.0059 (14)0.0022 (12)0.0086 (14)
N10.0242 (10)0.0359 (12)0.0355 (11)0.0008 (9)0.0081 (8)0.0002 (9)
N20.0248 (10)0.0316 (11)0.0366 (11)0.0006 (9)0.0067 (8)0.0003 (9)
N30.0234 (10)0.0341 (11)0.0291 (10)0.0007 (9)0.0035 (8)0.0019 (9)
N40.0244 (10)0.0406 (14)0.0441 (12)0.0041 (10)0.0062 (9)0.0117 (11)
N50.0239 (11)0.0490 (15)0.0401 (12)0.0041 (10)0.0022 (9)0.0090 (11)
N60.0231 (10)0.0304 (11)0.0359 (11)0.0018 (8)0.0081 (8)0.0020 (9)
N70.0219 (10)0.0259 (10)0.0313 (10)0.0031 (8)0.0075 (8)0.0006 (8)
N80.0227 (10)0.0277 (11)0.0376 (11)0.0007 (8)0.0087 (8)0.0017 (9)
N90.0201 (11)0.0537 (15)0.0346 (11)0.0020 (10)0.0017 (9)0.0090 (10)
N100.0240 (11)0.0359 (14)0.0611 (15)0.0073 (10)0.0104 (10)0.0137 (12)
O10.0304 (12)0.085 (2)0.0696 (16)0.0005 (12)0.0163 (11)0.0061 (14)
O20.0270 (10)0.0561 (14)0.0691 (15)0.0041 (9)0.0175 (9)0.0051 (12)
S10.0360 (4)0.0341 (4)0.0830 (6)0.0057 (3)0.0172 (4)0.0177 (4)
S20.0392 (4)0.0556 (5)0.0442 (4)0.0031 (3)0.0024 (3)0.0186 (4)
S30.0374 (4)0.0496 (4)0.0371 (3)0.0019 (3)0.0078 (3)0.0118 (3)
S40.0386 (4)0.0296 (4)0.0768 (6)0.0032 (3)0.0232 (4)0.0088 (4)
Geometric parameters (Å, º) top
C1—N11.450 (3)C22—H22B0.9700
C1—N21.477 (3)C23—N61.447 (3)
C1—H1A0.9700C23—N81.474 (3)
C1—H1B0.9700C23—H23A0.9700
C2—N11.447 (3)C23—H23B0.9700
C2—N31.466 (3)C24—N91.347 (3)
C2—H2A0.9700C24—N71.354 (3)
C2—H2B0.9700C24—S31.671 (3)
C3—N41.327 (3)C25—N81.347 (3)
C3—N21.373 (3)C25—N101.350 (4)
C3—S11.666 (3)C25—S41.671 (3)
C4—N31.341 (3)C26—N81.462 (3)
C4—N51.348 (3)C26—N71.473 (3)
C4—S21.672 (3)C26—C271.515 (3)
C5—N21.458 (3)C26—C331.579 (3)
C5—N31.466 (3)C27—C281.384 (4)
C5—C61.523 (3)C27—C321.388 (4)
C5—C121.584 (3)C28—C291.383 (4)
C6—C111.381 (4)C28—H280.9300
C6—C71.385 (4)C29—C301.356 (7)
C7—C81.397 (5)C29—H290.9300
C7—H70.9300C30—C311.363 (7)
C8—C91.363 (6)C30—H300.9300
C8—H80.9300C31—C321.383 (5)
C9—C101.372 (5)C31—H310.9300
C9—H90.9300C32—H320.9300
C10—C111.393 (4)C33—N101.443 (4)
C10—H100.9300C33—N91.457 (3)
C11—H110.9300C33—C341.527 (3)
C12—N51.442 (4)C34—C391.380 (4)
C12—N41.469 (4)C34—C351.385 (4)
C12—C131.514 (4)C35—C361.393 (5)
C13—C181.379 (4)C35—H350.9300
C13—C141.387 (5)C36—C371.363 (7)
C14—C151.397 (5)C36—H360.9300
C14—H140.9300C37—C381.354 (7)
C15—C161.354 (7)C37—H370.9300
C15—H150.9300C38—C391.387 (5)
C16—C171.351 (7)C38—H380.9300
C16—H160.9300C39—H390.9300
C17—C181.396 (5)C40—N61.480 (3)
C17—H170.9300C40—C411.523 (4)
C18—H180.9300C40—C421.527 (4)
C19—N11.478 (3)C40—H400.9800
C19—C211.521 (4)C41—O21.427 (4)
C19—C201.539 (4)C41—H41A0.9700
C19—H190.9800C41—H41B0.9700
C20—O11.420 (4)C42—H42A0.9600
C20—H20A0.9700C42—H42B0.9600
C20—H20B0.9700C42—H42C0.9600
C21—H21A0.9600N4—H4A0.83 (3)
C21—H21B0.9600N5—H5A0.79 (4)
C21—H21C0.9600N9—H9A0.85 (4)
C22—N61.451 (3)N10—H10A0.76 (4)
C22—N71.461 (3)O1—H10.96 (4)
C22—H22A0.9700O2—H20.97 (4)
N1—C1—N2113.0 (2)N8—C25—S4125.8 (2)
N1—C1—H1A109.0N10—C25—S4125.7 (2)
N2—C1—H1A109.0N8—C26—N7109.17 (19)
N1—C1—H1B109.0N8—C26—C27111.6 (2)
N2—C1—H1B109.0N7—C26—C27111.0 (2)
H1A—C1—H1B107.8N8—C26—C33102.74 (19)
N1—C2—N3111.8 (2)N7—C26—C33103.04 (19)
N1—C2—H2A109.3C27—C26—C33118.6 (2)
N3—C2—H2A109.3C28—C27—C32118.6 (3)
N1—C2—H2B109.3C28—C27—C26120.9 (2)
N3—C2—H2B109.3C32—C27—C26120.4 (3)
H2A—C2—H2B107.9C29—C28—C27120.1 (3)
N4—C3—N2109.3 (2)C29—C28—H28119.9
N4—C3—S1126.4 (2)C27—C28—H28119.9
N2—C3—S1124.3 (2)C30—C29—C28120.6 (4)
N3—C4—N5108.0 (2)C30—C29—H29119.7
N3—C4—S2126.1 (2)C28—C29—H29119.7
N5—C4—S2125.9 (2)C29—C30—C31120.1 (3)
N2—C5—N3109.1 (2)C29—C30—H30120.0
N2—C5—C6112.6 (2)C31—C30—H30120.0
N3—C5—C6111.6 (2)C30—C31—C32120.5 (4)
N2—C5—C12104.0 (2)C30—C31—H31119.7
N3—C5—C12101.38 (19)C32—C31—H31119.7
C6—C5—C12117.3 (2)C31—C32—C27120.0 (4)
C11—C6—C7119.8 (3)C31—C32—H32120.0
C11—C6—C5120.1 (3)C27—C32—H32120.0
C7—C6—C5120.1 (3)N10—C33—N9113.0 (2)
C6—C7—C8119.3 (3)N10—C33—C34111.0 (2)
C6—C7—H7120.4N9—C33—C34112.3 (2)
C8—C7—H7120.4N10—C33—C26101.4 (2)
C9—C8—C7120.7 (3)N9—C33—C26101.19 (19)
C9—C8—H8119.6C34—C33—C26117.3 (2)
C7—C8—H8119.6C39—C34—C35118.8 (3)
C8—C9—C10120.1 (3)C39—C34—C33121.3 (3)
C8—C9—H9119.9C35—C34—C33119.9 (3)
C10—C9—H9119.9C34—C35—C36119.6 (4)
C9—C10—C11120.0 (4)C34—C35—H35120.2
C9—C10—H10120.0C36—C35—H35120.2
C11—C10—H10120.0C37—C36—C35121.1 (4)
C6—C11—C10120.0 (3)C37—C36—H36119.5
C6—C11—H11120.0C35—C36—H36119.5
C10—C11—H11120.0C38—C37—C36119.3 (3)
N5—C12—N4113.5 (2)C38—C37—H37120.3
N5—C12—C13113.8 (2)C36—C37—H37120.3
N4—C12—C13111.4 (2)C37—C38—C39121.0 (4)
N5—C12—C5100.5 (2)C37—C38—H38119.5
N4—C12—C599.4 (2)C39—C38—H38119.5
C13—C12—C5117.2 (2)C34—C39—C38120.2 (4)
C18—C13—C14118.4 (3)C34—C39—H39119.9
C18—C13—C12121.9 (3)C38—C39—H39119.9
C14—C13—C12119.7 (3)N6—C40—C41107.5 (2)
C13—C14—C15120.4 (4)N6—C40—C42117.1 (2)
C13—C14—H14119.8C41—C40—C42109.8 (2)
C15—C14—H14119.8N6—C40—H40107.4
C16—C15—C14120.3 (4)C41—C40—H40107.4
C16—C15—H15119.8C42—C40—H40107.4
C14—C15—H15119.8O2—C41—C40111.0 (2)
C17—C16—C15119.9 (4)O2—C41—H41A109.4
C17—C16—H16120.1C40—C41—H41A109.4
C15—C16—H16120.1O2—C41—H41B109.4
C16—C17—C18121.2 (4)C40—C41—H41B109.4
C16—C17—H17119.4H41A—C41—H41B108.0
C18—C17—H17119.4C40—C42—H42A109.5
C13—C18—C17119.9 (4)C40—C42—H42B109.5
C13—C18—H18120.1H42A—C42—H42B109.5
C17—C18—H18120.1C40—C42—H42C109.5
N1—C19—C21117.5 (2)H42A—C42—H42C109.5
N1—C19—C20106.9 (2)H42B—C42—H42C109.5
C21—C19—C20109.9 (2)C2—N1—C1112.3 (2)
N1—C19—H19107.3C2—N1—C19117.7 (2)
C21—C19—H19107.3C1—N1—C19118.0 (2)
C20—C19—H19107.3C3—N2—C5110.4 (2)
O1—C20—C19111.1 (2)C3—N2—C1122.7 (2)
O1—C20—H20A109.4C5—N2—C1114.1 (2)
C19—C20—H20A109.4C4—N3—C2129.6 (2)
O1—C20—H20B109.4C4—N3—C5112.8 (2)
C19—C20—H20B109.4C2—N3—C5116.9 (2)
H20A—C20—H20B108.0C3—N4—C12114.8 (2)
C19—C21—H21A109.5C3—N4—H4A120 (2)
C19—C21—H21B109.5C12—N4—H4A125 (2)
H21A—C21—H21B109.5C4—N5—C12114.1 (2)
C19—C21—H21C109.5C4—N5—H5A123 (3)
H21A—C21—H21C109.5C12—N5—H5A123 (3)
H21B—C21—H21C109.5C23—N6—C22111.9 (2)
N6—C22—N7112.5 (2)C23—N6—C40119.7 (2)
N6—C22—H22A109.1C22—N6—C40116.1 (2)
N7—C22—H22A109.1C24—N7—C22126.3 (2)
N6—C22—H22B109.1C24—N7—C26112.2 (2)
N7—C22—H22B109.1C22—N7—C26114.94 (19)
H22A—C22—H22B107.8C25—N8—C26112.6 (2)
N6—C23—N8112.5 (2)C25—N8—C23127.2 (2)
N6—C23—H23A109.1C26—N8—C23116.6 (2)
N8—C23—H23A109.1C24—N9—C33114.6 (2)
N6—C23—H23B109.1C24—N9—H9A121 (2)
N8—C23—H23B109.1C33—N9—H9A124 (2)
H23A—C23—H23B107.8C25—N10—C33114.5 (2)
N9—C24—N7108.6 (2)C25—N10—H10A122 (3)
N9—C24—S3126.1 (2)C33—N10—H10A122 (3)
N7—C24—S3125.2 (2)C20—O1—H1103 (3)
N8—C25—N10108.5 (2)C41—O2—H297 (2)
N2—C5—C6—C11145.7 (3)N2—C1—N1—C1990.0 (3)
N3—C5—C6—C1122.7 (4)C21—C19—N1—C248.8 (3)
C12—C5—C6—C1193.7 (3)C20—C19—N1—C275.3 (3)
N2—C5—C6—C734.4 (3)C21—C19—N1—C191.1 (3)
N3—C5—C6—C7157.5 (2)C20—C19—N1—C1144.8 (2)
C12—C5—C6—C786.2 (3)N4—C3—N2—C58.3 (3)
C11—C6—C7—C80.3 (5)S1—C3—N2—C5173.3 (2)
C5—C6—C7—C8179.5 (3)N4—C3—N2—C1147.4 (2)
C6—C7—C8—C91.2 (6)S1—C3—N2—C134.1 (4)
C7—C8—C9—C100.9 (6)N3—C5—N2—C393.7 (2)
C8—C9—C10—C110.2 (6)C6—C5—N2—C3141.8 (2)
C7—C6—C11—C100.8 (5)C12—C5—N2—C313.8 (3)
C5—C6—C11—C10179.4 (3)N3—C5—N2—C149.2 (3)
C9—C10—C11—C61.0 (5)C6—C5—N2—C175.3 (3)
N2—C5—C12—N5129.6 (2)C12—C5—N2—C1156.73 (19)
N3—C5—C12—N516.4 (2)N1—C1—N2—C384.9 (3)
C6—C5—C12—N5105.4 (2)N1—C1—N2—C552.9 (3)
N2—C5—C12—N413.3 (2)N5—C4—N3—C2166.6 (3)
N3—C5—C12—N499.8 (2)S2—C4—N3—C214.8 (4)
C6—C5—C12—N4138.4 (2)N5—C4—N3—C53.4 (3)
N2—C5—C12—C13106.7 (3)S2—C4—N3—C5175.1 (2)
N3—C5—C12—C13140.2 (2)N1—C2—N3—C4119.3 (3)
C6—C5—C12—C1318.4 (4)N1—C2—N3—C550.4 (3)
N5—C12—C13—C1818.6 (4)N2—C5—N3—C4122.2 (2)
N4—C12—C13—C18148.3 (3)C6—C5—N3—C4112.8 (2)
C5—C12—C13—C1898.2 (3)C12—C5—N3—C413.0 (3)
N5—C12—C13—C14160.7 (3)N2—C5—N3—C249.2 (3)
N4—C12—C13—C1430.9 (4)C6—C5—N3—C275.9 (3)
C5—C12—C13—C1482.6 (3)C12—C5—N3—C2158.4 (2)
C18—C13—C14—C151.1 (5)N2—C3—N4—C121.8 (3)
C12—C13—C14—C15179.7 (3)S1—C3—N4—C12176.6 (2)
C13—C14—C15—C161.9 (6)N5—C12—N4—C3115.7 (3)
C14—C15—C16—C171.4 (7)C13—C12—N4—C3114.4 (3)
C15—C16—C17—C180.2 (7)C5—C12—N4—C39.8 (3)
C14—C13—C18—C170.2 (5)N3—C4—N5—C129.4 (3)
C12—C13—C18—C17179.1 (3)S2—C4—N5—C12172.0 (2)
C16—C17—C18—C130.7 (6)N4—C12—N5—C488.6 (3)
N1—C19—C20—O143.9 (3)C13—C12—N5—C4142.7 (2)
C21—C19—C20—O1172.5 (3)C5—C12—N5—C416.6 (3)
N8—C26—C27—C28147.6 (3)N8—C23—N6—C2250.4 (3)
N7—C26—C27—C2825.7 (3)N8—C23—N6—C4090.3 (3)
C33—C26—C27—C2893.3 (3)N7—C22—N6—C2353.0 (3)
N8—C26—C27—C3232.0 (3)N7—C22—N6—C4089.2 (2)
N7—C26—C27—C32154.0 (2)C41—C40—N6—C2377.8 (3)
C33—C26—C27—C3287.0 (3)C42—C40—N6—C2346.3 (3)
C32—C27—C28—C292.4 (5)C41—C40—N6—C22143.0 (2)
C26—C27—C28—C29177.3 (3)C42—C40—N6—C2292.9 (3)
C27—C28—C29—C302.2 (5)N9—C24—N7—C22155.4 (2)
C28—C29—C30—C310.2 (6)S3—C24—N7—C2225.8 (4)
C29—C30—C31—C322.4 (6)N9—C24—N7—C265.6 (3)
C30—C31—C32—C272.2 (6)S3—C24—N7—C26175.58 (19)
C28—C27—C32—C310.2 (5)N6—C22—N7—C2495.6 (3)
C26—C27—C32—C31179.5 (3)N6—C22—N7—C2653.5 (3)
N8—C26—C33—N103.8 (2)N8—C26—N7—C24104.8 (2)
N7—C26—C33—N10117.3 (2)C27—C26—N7—C24131.8 (2)
C27—C26—C33—N10119.7 (2)C33—C26—N7—C243.8 (3)
N8—C26—C33—N9112.7 (2)N8—C26—N7—C2248.6 (3)
N7—C26—C33—N90.8 (2)C27—C26—N7—C2274.8 (3)
C27—C26—C33—N9123.8 (2)C33—C26—N7—C22157.26 (19)
N8—C26—C33—C34124.9 (2)N10—C25—N8—C263.4 (3)
N7—C26—C33—C34121.7 (2)S4—C25—N8—C26174.25 (19)
C27—C26—C33—C341.3 (3)N10—C25—N8—C23154.3 (2)
N10—C33—C34—C39150.1 (3)S4—C25—N8—C2328.0 (4)
N9—C33—C34—C3922.6 (4)N7—C26—N8—C25113.5 (2)
C26—C33—C34—C3994.0 (3)C27—C26—N8—C25123.5 (2)
N10—C33—C34—C3530.1 (4)C33—C26—N8—C254.6 (3)
N9—C33—C34—C35157.7 (3)N7—C26—N8—C2346.8 (3)
C26—C33—C34—C3585.7 (3)C27—C26—N8—C2376.2 (3)
C39—C34—C35—C361.0 (5)C33—C26—N8—C23155.7 (2)
C33—C34—C35—C36179.2 (3)N6—C23—N8—C25107.6 (3)
C34—C35—C36—C370.4 (6)N6—C23—N8—C2649.4 (3)
C35—C36—C37—C380.7 (7)N7—C24—N9—C335.1 (3)
C36—C37—C38—C390.5 (6)S3—C24—N9—C33176.0 (2)
C35—C34—C39—C382.2 (5)N10—C33—N9—C24105.1 (3)
C33—C34—C39—C38178.1 (3)C34—C33—N9—C24128.4 (3)
C37—C38—C39—C342.0 (5)C26—C33—N9—C242.5 (3)
N6—C40—C41—O243.7 (3)N8—C25—N10—C330.5 (3)
C42—C40—C41—O2172.1 (2)S4—C25—N10—C33177.2 (2)
N3—C2—N1—C149.8 (3)N9—C33—N10—C25105.3 (3)
N3—C2—N1—C1992.3 (3)C34—C33—N10—C25127.6 (2)
N2—C1—N1—C252.0 (3)C26—C33—N10—C252.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N10—H10A···S3i0.76 (4)2.86 (4)3.584 (3)160 (3)
N9—H9A···S4ii0.85 (4)2.79 (4)3.542 (3)148 (3)
N9—H9A···O2iii0.85 (4)2.36 (4)2.913 (3)124 (3)
N5—H5A···S1iv0.79 (4)2.63 (4)3.400 (2)169 (3)
N4—H4A···O1iii0.83 (3)2.39 (3)2.940 (3)124 (3)
C22—H22B···S4v0.972.853.578 (3)132
C20—H20B···S1vi0.972.853.548 (3)129
O1—H1···N10.96 (4)2.04 (3)2.685 (3)123 (3)
O2—H2···N60.97 (4)1.95 (4)2.682 (3)130 (3)
Symmetry codes: (i) x+2, y+1/2, z+2; (ii) x+2, y1/2, z+2; (iii) x+1, y, z; (iv) x+1, y+1/2, z+1; (v) x+1, y1/2, z+2; (vi) x, y+1/2, z+1.

Experimental details

Crystal data
Chemical formulaC21H23N5OS2
Mr425.58
Crystal system, space groupMonoclinic, P21
Temperature (K)298
a, b, c (Å)9.0030 (9), 12.6382 (13), 18.5830 (2)
β (°) 100.169 (2)
V3)2081.2 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.28
Crystal size (mm)0.25 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART 4K CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
14076, 9634, 8871
Rint0.020
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.133, 1.08
No. of reflections9634
No. of parameters543
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.39, 0.25
Absolute structureFlack (1983), 4300 Friedel pairs
Absolute structure parameter0.04 (6)

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008) and pubCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N10—H10A···S3i0.76 (4)2.86 (4)3.584 (3)160 (3)
N9—H9A···S4ii0.85 (4)2.79 (4)3.542 (3)148 (3)
N9—H9A···O2iii0.85 (4)2.36 (4)2.913 (3)124 (3)
N5—H5A···S1iv0.79 (4)2.63 (4)3.400 (2)169 (3)
N4—H4A···O1iii0.83 (3)2.39 (3)2.940 (3)124 (3)
C22—H22B···S4v0.972.853.578 (3)132
C20—H20B···S1vi0.972.853.548 (3)129
O1—H1···N10.96 (4)2.04 (3)2.685 (3)123 (3)
O2—H2···N60.97 (4)1.95 (4)2.682 (3)130 (3)
Symmetry codes: (i) x+2, y+1/2, z+2; (ii) x+2, y1/2, z+2; (iii) x+1, y, z; (iv) x+1, y+1/2, z+1; (v) x+1, y1/2, z+2; (vi) x, y+1/2, z+1.
 

Acknowledgements

The authors are grateful to the Central China Normal University for financial support and to Dr Xiang-Gao Meng for the X-ray data collection.

References

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