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In the crystal structure of the title compound, C21H18N6S3·H2O, the ligands are held together through π–π stacking inter­actions and O—H...N hydrogen bonds involving the water mol­ecule.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805016132/is6077sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805016132/is6077Isup2.hkl
Contains datablock I

CCDC reference: 274448

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.032
  • wR factor = 0.086
  • Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.94
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 28.10 From the CIF: _diffrn_reflns_theta_full 28.10 From the CIF: _reflns_number_total 4892 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 5184 Completeness (_total/calc) 94.37% PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.01 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 H2 O
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT-Plus (Bruker, 1997); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: XCIF (Bruker, 2001).

2,4,6-Tris(4-pyridylmethylsulfanyl)-1,3,5-triazine monohydrate top
Crystal data top
C21H18N6S3·H2OZ = 2
Mr = 468.61F(000) = 488
Triclinic, P1Dx = 1.465 Mg m3
Hall symbol: -P1Mo Kα radiation, λ = 0.71073 Å
a = 8.436 (1) ÅCell parameters from 5238 reflections
b = 10.8759 (12) Åθ = 2.3–28.0°
c = 12.1904 (14) ŵ = 0.38 mm1
α = 73.9052 (18)°T = 150 K
β = 85.9455 (19)°Needle, light yellow
γ = 81.3899 (19)°0.55 × 0.11 × 0.09 mm
V = 1062.0 (4) Å3
Data collection top
Bruker SMART 1000 CCD
diffractometer
4892 independent reflections
Radiation source: fine-focus sealed tube4257 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
ω scansθmax = 28.1°, θmin = 1.7°
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
h = 1011
Tmin = 0.89, Tmax = 0.97k = 1314
10553 measured reflectionsl = 1616
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0371P)2 + 0.6826P]
where P = (Fo2 + 2Fc2)/3
4892 reflections(Δ/σ)max < 0.001
286 parametersΔρmax = 0.42 e Å3
0 restraintsΔρmin = 0.21 e Å3
Special details top

Experimental. In a thin film of perfluoropolyether oil on a mohair fibre

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
S10.87918 (5)0.19836 (4)0.89529 (3)0.02397 (10)
S20.55688 (5)0.01210 (4)1.20268 (3)0.02310 (10)
S30.84192 (5)0.29954 (4)0.84877 (3)0.02179 (9)
N10.72169 (15)0.08606 (12)1.04068 (11)0.0212 (3)
N20.85858 (15)0.05142 (12)0.88690 (11)0.0209 (3)
N30.70636 (15)0.13932 (12)1.02660 (11)0.0213 (3)
N40.81381 (18)0.41694 (14)1.50269 (12)0.0310 (3)
N50.72276 (18)0.08986 (15)0.47199 (12)0.0312 (3)
N60.26648 (17)0.56319 (14)0.78083 (12)0.0294 (3)
C10.81496 (18)0.06215 (15)0.94414 (13)0.0208 (3)
C20.79596 (17)0.14939 (14)0.93122 (12)0.0195 (3)
C30.67450 (17)0.01846 (15)1.07754 (12)0.0200 (3)
C40.99446 (18)0.13221 (15)0.76648 (13)0.0229 (3)
H4A1.06690.07690.78390.028*
H4B1.06230.20430.74400.028*
C50.73201 (18)0.41031 (15)0.92475 (13)0.0223 (3)
H5A0.72030.36421.00660.027*
H5B0.79400.48240.91900.027*
C60.51014 (18)0.15217 (15)1.24530 (13)0.0232 (3)
H6A0.39790.15121.27520.028*
H6B0.51720.18501.17680.028*
C70.7026 (2)0.03241 (17)0.52473 (15)0.0294 (4)
H70.62780.07050.49450.035*
C80.78409 (19)0.10693 (16)0.62065 (14)0.0246 (3)
H80.76460.19330.65470.029*
C90.89465 (18)0.05382 (15)0.66644 (13)0.0205 (3)
C100.91642 (19)0.07273 (16)0.61288 (14)0.0247 (3)
H100.99010.11340.64150.030*
C110.8293 (2)0.13959 (16)0.51681 (14)0.0292 (4)
H110.84680.22610.48080.035*
C120.2935 (2)0.44587 (16)0.85479 (15)0.0275 (3)
H120.20740.39580.87390.033*
C130.43934 (19)0.39340 (15)0.90493 (14)0.0238 (3)
H130.45150.31020.95770.029*
C140.56805 (18)0.46416 (15)0.87706 (13)0.0217 (3)
C150.5398 (2)0.58715 (16)0.80299 (14)0.0276 (3)
H150.62310.64000.78370.033*
C160.3894 (2)0.63247 (17)0.75719 (15)0.0305 (4)
H160.37270.71680.70650.037*
C170.6540 (2)0.40328 (18)1.51432 (15)0.0331 (4)
H170.60730.45371.58190.040*
C180.5523 (2)0.31977 (17)1.43357 (14)0.0284 (3)
H180.43940.31411.44600.034*
C190.61733 (18)0.24437 (15)1.33425 (13)0.0212 (3)
C200.78324 (19)0.25994 (15)1.32022 (14)0.0238 (3)
H200.83310.21181.25290.029*
C210.8753 (2)0.34639 (16)1.40544 (14)0.0269 (3)
H210.98860.35611.39420.032*
O10.93818 (16)0.42049 (13)0.72339 (12)0.0323 (3)
H1A0.931 (3)0.428 (2)0.658 (2)0.039*
H1B1.038 (3)0.422 (2)0.7274 (19)0.039*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0311 (2)0.01872 (19)0.02043 (19)0.00019 (15)0.00035 (15)0.00449 (14)
S20.0255 (2)0.02197 (19)0.01929 (18)0.00003 (14)0.00178 (14)0.00378 (14)
S30.02273 (18)0.01994 (19)0.02075 (18)0.00196 (14)0.00087 (14)0.00318 (14)
N10.0227 (6)0.0217 (6)0.0181 (6)0.0012 (5)0.0021 (5)0.0040 (5)
N20.0214 (6)0.0210 (6)0.0192 (6)0.0007 (5)0.0025 (5)0.0041 (5)
N30.0231 (6)0.0200 (6)0.0189 (6)0.0005 (5)0.0019 (5)0.0032 (5)
N40.0348 (8)0.0276 (7)0.0267 (7)0.0008 (6)0.0061 (6)0.0025 (6)
N50.0312 (8)0.0319 (8)0.0266 (7)0.0054 (6)0.0047 (6)0.0058 (6)
N60.0258 (7)0.0333 (8)0.0283 (7)0.0019 (6)0.0044 (6)0.0093 (6)
C10.0207 (7)0.0222 (7)0.0189 (7)0.0007 (6)0.0049 (5)0.0053 (6)
C20.0187 (7)0.0209 (7)0.0182 (7)0.0007 (5)0.0052 (5)0.0038 (6)
C30.0187 (7)0.0228 (7)0.0168 (7)0.0001 (6)0.0043 (5)0.0031 (6)
C40.0214 (7)0.0251 (8)0.0221 (7)0.0001 (6)0.0001 (6)0.0078 (6)
C50.0236 (7)0.0210 (7)0.0224 (7)0.0015 (6)0.0019 (6)0.0065 (6)
C60.0203 (7)0.0250 (8)0.0232 (7)0.0037 (6)0.0021 (6)0.0041 (6)
C70.0236 (8)0.0352 (9)0.0309 (9)0.0007 (7)0.0049 (6)0.0121 (7)
C80.0231 (7)0.0231 (8)0.0270 (8)0.0028 (6)0.0002 (6)0.0065 (6)
C90.0192 (7)0.0227 (7)0.0191 (7)0.0000 (6)0.0027 (5)0.0072 (6)
C100.0256 (8)0.0237 (8)0.0257 (8)0.0047 (6)0.0017 (6)0.0080 (6)
C110.0347 (9)0.0230 (8)0.0266 (8)0.0014 (7)0.0042 (7)0.0037 (6)
C120.0255 (8)0.0278 (8)0.0326 (9)0.0047 (6)0.0006 (6)0.0130 (7)
C130.0263 (8)0.0196 (7)0.0261 (8)0.0021 (6)0.0013 (6)0.0074 (6)
C140.0238 (7)0.0227 (7)0.0196 (7)0.0014 (6)0.0001 (6)0.0084 (6)
C150.0273 (8)0.0250 (8)0.0274 (8)0.0042 (6)0.0007 (6)0.0020 (7)
C160.0312 (9)0.0272 (9)0.0272 (8)0.0012 (7)0.0012 (7)0.0001 (7)
C170.0368 (9)0.0305 (9)0.0256 (8)0.0036 (7)0.0029 (7)0.0016 (7)
C180.0241 (8)0.0288 (9)0.0288 (8)0.0021 (6)0.0025 (6)0.0037 (7)
C190.0232 (7)0.0198 (7)0.0213 (7)0.0023 (6)0.0022 (6)0.0067 (6)
C200.0230 (7)0.0240 (8)0.0235 (8)0.0035 (6)0.0010 (6)0.0045 (6)
C210.0240 (8)0.0248 (8)0.0310 (8)0.0013 (6)0.0039 (6)0.0064 (7)
O10.0269 (6)0.0360 (7)0.0332 (7)0.0018 (5)0.0042 (5)0.0084 (6)
Geometric parameters (Å, º) top
S1—C11.7452 (16)C7—C81.385 (2)
S1—C41.8155 (16)C7—H70.9500
S2—C31.7505 (15)C8—C91.389 (2)
S2—C61.8124 (16)C8—H80.9500
S3—C21.7469 (15)C9—C101.384 (2)
S3—C51.8253 (16)C10—C111.389 (2)
N1—C31.332 (2)C10—H100.9500
N1—C11.354 (2)C11—H110.9500
N2—C11.330 (2)C12—C131.384 (2)
N2—C21.348 (2)C12—H120.9500
N3—C21.329 (2)C13—C141.393 (2)
N3—C31.347 (2)C13—H130.9500
N4—C171.336 (2)C14—C151.388 (2)
N4—C211.338 (2)C15—C161.387 (2)
N5—C111.333 (2)C15—H150.9500
N5—C71.337 (2)C16—H160.9500
N6—C121.340 (2)C17—C181.385 (2)
N6—C161.341 (2)C17—H170.9500
C4—C91.509 (2)C18—C191.389 (2)
C4—H4A0.9900C18—H180.9500
C4—H4B0.9900C19—C201.389 (2)
C5—C141.509 (2)C20—C211.386 (2)
C5—H5A0.9900C20—H200.9500
C5—H5B0.9900C21—H210.9500
C6—C191.504 (2)O1—H1A0.83 (2)
C6—H6A0.9900O1—H1B0.84 (2)
C6—H6B0.9900
C1—S1—C4102.09 (7)C9—C8—H8120.4
C3—S2—C6103.35 (7)C10—C9—C8117.34 (14)
C2—S3—C5102.59 (7)C10—C9—C4120.78 (14)
C3—N1—C1113.13 (13)C8—C9—C4121.80 (14)
C1—N2—C2113.84 (13)C9—C10—C11119.26 (15)
C2—N3—C3113.88 (13)C9—C10—H10120.4
C17—N4—C21116.49 (14)C11—C10—H10120.4
C11—N5—C7116.08 (15)N5—C11—C10124.04 (16)
C12—N6—C16116.64 (14)N5—C11—H11118.0
N2—C1—N1126.41 (14)C10—C11—H11118.0
N2—C1—S1119.86 (12)N6—C12—C13123.87 (16)
N1—C1—S1113.72 (11)N6—C12—H12118.1
N3—C2—N2126.04 (14)C13—C12—H12118.1
N3—C2—S3120.82 (12)C12—C13—C14119.18 (15)
N2—C2—S3113.13 (11)C12—C13—H13120.4
N1—C3—N3126.57 (14)C14—C13—H13120.4
N1—C3—S2121.97 (12)C15—C14—C13117.27 (15)
N3—C3—S2111.46 (11)C15—C14—C5120.90 (14)
C9—C4—S1114.55 (11)C13—C14—C5121.83 (14)
C9—C4—H4A108.6C16—C15—C14119.68 (16)
S1—C4—H4A108.6C16—C15—H15120.2
C9—C4—H4B108.6C14—C15—H15120.2
S1—C4—H4B108.6N6—C16—C15123.30 (16)
H4A—C4—H4B107.6N6—C16—H16118.3
C14—C5—S3111.80 (10)C15—C16—H16118.3
C14—C5—H5A109.3N4—C17—C18123.79 (16)
S3—C5—H5A109.3N4—C17—H17118.1
C14—C5—H5B109.3C18—C17—H17118.1
S3—C5—H5B109.3C17—C18—C19119.32 (15)
H5A—C5—H5B107.9C17—C18—H18120.3
C19—C6—S2114.65 (11)C19—C18—H18120.3
C19—C6—H6A108.6C20—C19—C18117.31 (14)
S2—C6—H6A108.6C20—C19—C6122.10 (14)
C19—C6—H6B108.6C18—C19—C6120.58 (14)
S2—C6—H6B108.6C21—C20—C19119.29 (15)
H6A—C6—H6B107.6C21—C20—H20120.4
N5—C7—C8124.10 (16)C19—C20—H20120.4
N5—C7—H7118.0N4—C21—C20123.76 (15)
C8—C7—H7118.0N4—C21—H21118.1
C7—C8—C9119.18 (15)C20—C21—H21118.1
C7—C8—H8120.4H1A—O1—H1B102 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N4i0.83 (2)2.16 (2)2.944 (2)157 (2)
O1—H1B···N6ii0.84 (2)2.05 (2)2.872 (2)165 (2)
Symmetry codes: (i) x, y, z1; (ii) x+1, y1, z.
 

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