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The title compound, C11H10N4S·H2O, displays an intramol­eculear Namido...Npyridyl hydrogen bond [2.652 (2) Å] that locks the thio­urea unit and one pyridyl ring into coplanarity [dihedral angle 2.7 (1)°]. The second pyridyl ring is also coplanar with the thio­urea unit [dihedral angle 2.9 (1)°]. Its attached N atom interacts with the lattice water mol­ecule to form a helical hydrogen-bonded chain that runs parallel to the b axis of the orthorhombic unit cell; adjacent chains are linked into a layer-like architecture by another hydrogen bond between the water mol­ecule and the double-bonded S atom.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803021597/su6048sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803021597/su6048Isup2.hkl
Contains datablock I

CCDC reference: 226933

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.041
  • wR factor = 0.089
  • Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.98
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - C11 = 5.38 su PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 2724 Count of symmetry unique reflns 1641 Completeness (_total/calc) 166.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1083 Fraction of Friedel pairs measured 0.660 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 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 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

1,3-Di-2-pyridylthiourea monohydrate top
Crystal data top
C11H10N4S·H2ODx = 1.344 Mg m3
Mr = 248.31Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 1662 reflections
a = 6.1921 (1) Åθ = 2.4–23.3°
b = 11.9609 (3) ŵ = 0.25 mm1
c = 16.5666 (3) ÅT = 298 K
V = 1226.97 (4) Å3Block, colorless
Z = 40.37 × 0.24 × 0.22 mm
F(000) = 520
Data collection top
Bruker APEX area-detector
diffractometer
2320 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 27.5°, θmin = 2.1°
φ and ω scansh = 77
7255 measured reflectionsk = 159
2724 independent reflectionsl = 2121
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)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.089 w = 1/[σ2(Fo2) + (0.0493P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max = 0.001
2724 reflectionsΔρmax = 0.30 e Å3
170 parametersΔρmin = 0.17 e Å3
4 restraintsAbsolute structure: Flack (1983), 1119 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.06 (8)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.3147 (1)1.05268 (5)0.56244 (3)0.0592 (2)
O1w0.1361 (3)0.6749 (2)0.8582 (1)0.0687 (5)
N10.0470 (3)0.7789 (1)0.7077 (1)0.0551 (4)
N20.2136 (3)0.9077 (1)0.6831 (1)0.0492 (4)
N30.4648 (3)0.8991 (2)0.8126 (1)0.0559 (5)
N40.5214 (3)1.0137 (1)0.6985 (1)0.0477 (4)
C10.0265 (3)0.8544 (2)0.6540 (1)0.0455 (5)
C20.0750 (4)0.8731 (2)0.5804 (1)0.0564 (6)
C30.2585 (4)0.8112 (2)0.5625 (1)0.0657 (6)
C40.3352 (4)0.7338 (2)0.6164 (2)0.0674 (6)
C50.2252 (4)0.7217 (2)0.6881 (2)0.0665 (6)
C60.5345 (5)0.8615 (2)0.8852 (1)0.0658 (6)
C70.7216 (4)0.8965 (2)0.9211 (1)0.0685 (7)
C80.8457 (4)0.9754 (2)0.8812 (1)0.0680 (6)
C90.7808 (4)1.0150 (2)0.8069 (1)0.0569 (5)
C100.5884 (3)0.9739 (2)0.7748 (1)0.0473 (5)
C110.3453 (3)0.9860 (2)0.6515 (1)0.0457 (5)
H1w10.077 (4)0.713 (2)0.821 (1)0.09 (1)*
H1w20.040 (3)0.649 (2)0.889 (1)0.09 (1)*
H2n0.255 (3)0.885 (2)0.729 (1)0.06 (1)*
H4n0.600 (3)1.064 (1)0.678 (1)0.05 (1)*
H20.02150.92560.54410.068*
H30.32970.82230.51370.079*
H40.45690.69110.60500.081*
H50.27810.67030.72530.080*
H60.45050.80890.91210.079*
H70.76420.86820.97090.082*
H80.97271.00160.90440.082*
H90.86281.06750.77910.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0517 (3)0.0755 (4)0.0505 (3)0.0052 (3)0.0030 (3)0.0117 (3)
O1w0.055 (1)0.076 (1)0.075 (1)0.003 (1)0.003 (1)0.010 (1)
N10.045 (1)0.052 (1)0.069 (1)0.002 (1)0.002 (1)0.008 (1)
N20.043 (1)0.059 (1)0.046 (1)0.004 (1)0.003 (1)0.005 (1)
N30.052 (1)0.066 (1)0.049 (1)0.009 (1)0.003 (1)0.002 (1)
N40.042 (1)0.054 (1)0.048 (1)0.006 (1)0.002 (1)0.002 (1)
C10.036 (1)0.047 (1)0.054 (1)0.004 (1)0.003 (1)0.007 (1)
C20.055 (1)0.062 (1)0.053 (1)0.005 (1)0.004 (1)0.000 (1)
C30.058 (1)0.073 (1)0.066 (1)0.001 (1)0.013 (1)0.006 (1)
C40.048 (1)0.064 (1)0.090 (2)0.009 (1)0.008 (1)0.003 (1)
C50.056 (2)0.060 (1)0.083 (2)0.011 (1)0.001 (1)0.012 (1)
C60.069 (2)0.075 (1)0.054 (1)0.011 (1)0.003 (1)0.007 (1)
C70.068 (2)0.084 (2)0.054 (1)0.002 (1)0.015 (1)0.003 (1)
C80.057 (1)0.082 (2)0.066 (1)0.006 (1)0.017 (1)0.010 (1)
C90.049 (1)0.063 (1)0.058 (1)0.008 (1)0.003 (1)0.006 (1)
C100.044 (1)0.050 (1)0.048 (1)0.003 (1)0.004 (1)0.009 (1)
C110.040 (1)0.050 (1)0.047 (1)0.004 (1)0.007 (1)0.006 (1)
Geometric parameters (Å, º) top
S1—C111.688 (2)C8—C91.378 (3)
N1—C51.339 (3)C9—C101.394 (3)
N1—C11.346 (2)O1w—H1w10.85 (1)
N2—C111.348 (3)O1w—H1w20.84 (1)
N2—C11.408 (3)N2—H2n0.85 (1)
N3—C101.335 (3)N4—H4n0.84 (1)
N3—C61.354 (3)C2—H20.93
N4—C111.381 (3)C3—H30.93
N4—C101.412 (2)C4—H40.93
C1—C21.390 (3)C5—H50.93
C2—C31.388 (3)C6—H60.93
C3—C41.371 (3)C7—H70.93
C4—C51.376 (3)C8—H80.93
C6—C71.369 (3)C9—H90.93
C7—C81.385 (3)
C1—N1—C5117.5 (2)H1w1—O1w—H1w2109 (3)
C11—N2—C1132.8 (2)C11—N2—H2n113 (2)
C6—N3—C10117.2 (2)C1—N2—H2n114 (2)
C10—N4—C11131.0 (2)C11—N4—H4n114 (1)
N1—C1—C2122.3 (2)C10—N4—H4n115 (1)
N1—C1—N2110.8 (2)C3—C2—H2120.9
C2—C1—N2126.9 (2)C1—C2—H2120.9
C1—C2—C3118.2 (2)C4—C3—H3119.9
C2—C3—C4120.3 (2)C2—C3—H3119.9
C3—C4—C5117.5 (2)C3—C4—H4121.2
N1—C5—C4124.3 (2)C5—C4—H4121.2
N3—C6—C7123.7 (2)N1—C5—H5117.9
C6—C7—C8118.0 (2)C4—C5—H5117.9
C7—C8—C9119.9 (2)N3—C6—H6118.2
C8—C9—C10118.0 (2)C7—C6—H6118.2
N3—C10—C9123.1 (2)C6—C7—H7121.0
N3—C10—N4118.6 (2)C8—C7—H7121.0
C9—C10—N4118.3 (2)C9—C8—H8120.0
N2—C11—N4115.2 (2)C7—C8—H8120.0
N2—C11—S1126.9 (2)C8—C9—H9121.0
N4—C11—S1117.9 (2)C10—C9—H9121.0
C5—N1—C1—C20.5 (3)C6—C7—C8—C90.9 (4)
C5—N1—C1—N2179.8 (2)C7—C8—C9—C100.5 (3)
C11—N2—C1—N1178.6 (2)C6—N3—C10—C90.9 (3)
C11—N2—C1—C21.1 (3)C6—N3—C10—N4179.2 (2)
N1—C1—C2—C30.0 (3)C8—C9—C10—N30.4 (3)
N2—C1—C2—C3179.7 (2)C8—C9—C10—N4179.7 (2)
C1—C2—C3—C40.2 (3)C11—N4—C10—N32.4 (3)
C2—C3—C4—C50.8 (3)C11—N4—C10—C9177.7 (2)
C1—N1—C5—C41.1 (3)C1—N2—C11—N4177.2 (2)
C3—C4—C5—N11.2 (4)C1—N2—C11—S13.5 (3)
C10—N3—C6—C70.5 (3)C10—N4—C11—N20.1 (3)
N3—C6—C7—C80.4 (4)C10—N4—C11—S1179.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2n···N30.85 (1)1.90 (2)2.652 (2)146 (2)
N4—H4n···O1wi0.84 (1)2.19 (1)3.016 (2)166 (2)
O1w—H1w1···N10.85 (1)2.18 (1)3.008 (2)166 (2)
O1w—H1w2···S1ii0.84 (1)2.61 (1)3.414 (2)161 (2)
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x, y1/2, z+3/2.
 

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