1,3-Di-2-pyridyl­thio­urea monohydrate

The title compound, C₁₁H₁₀N₄S·H₂O, displays an intramol­eculear N_amido...N_pyridyl 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.

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

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Computing details

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

Crystal data

C11H10N4S·H2O	Dx = 1.344 Mg m^−3
Mr = 248.31	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1662 reflections
a = 6.1921 (1) Å	θ = 2.4–23.3°
b = 11.9609 (3) Å	µ = 0.25 mm^−1
c = 16.5666 (3) Å	T = 298 K
V = 1226.97 (4) Å^3	Block, colorless
Z = 4	0.37 × 0.24 × 0.22 mm
F(000) = 520

Data collection

Bruker APEX area-detector diffractometer	2320 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Graphite monochromator	θmax = 27.5°, θmin = 2.1°
φ and ω scans	h = −7→7
7255 measured reflections	k = −15→9
2724 independent reflections	l = −21→21

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.089	w = 1/[σ^2(Fo^2) + (0.0493P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.95	(Δ/σ)max = 0.001
2724 reflections	Δρmax = 0.30 e Å^−3
170 parameters	Δρmin = −0.17 e Å^−3
4 restraints	Absolute structure: Flack (1983), 1119 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.06 (8)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.3147 (1)	1.05268 (5)	0.56244 (3)	0.0592 (2)
O1w	0.1361 (3)	0.6749 (2)	0.8582 (1)	0.0687 (5)
N1	−0.0470 (3)	0.7789 (1)	0.7077 (1)	0.0551 (4)
N2	0.2136 (3)	0.9077 (1)	0.6831 (1)	0.0492 (4)
N3	0.4648 (3)	0.8991 (2)	0.8126 (1)	0.0559 (5)
N4	0.5214 (3)	1.0137 (1)	0.6985 (1)	0.0477 (4)
C1	0.0265 (3)	0.8544 (2)	0.6540 (1)	0.0455 (5)
C2	−0.0750 (4)	0.8731 (2)	0.5804 (1)	0.0564 (6)
C3	−0.2585 (4)	0.8112 (2)	0.5625 (1)	0.0657 (6)
C4	−0.3352 (4)	0.7338 (2)	0.6164 (2)	0.0674 (6)
C5	−0.2252 (4)	0.7217 (2)	0.6881 (2)	0.0665 (6)
C6	0.5345 (5)	0.8615 (2)	0.8852 (1)	0.0658 (6)
C7	0.7216 (4)	0.8965 (2)	0.9211 (1)	0.0685 (7)
C8	0.8457 (4)	0.9754 (2)	0.8812 (1)	0.0680 (6)
C9	0.7808 (4)	1.0150 (2)	0.8069 (1)	0.0569 (5)
C10	0.5884 (3)	0.9739 (2)	0.7748 (1)	0.0473 (5)
C11	0.3453 (3)	0.9860 (2)	0.6515 (1)	0.0457 (5)
H1w1	0.077 (4)	0.713 (2)	0.821 (1)	0.09 (1)*
H1w2	0.040 (3)	0.649 (2)	0.889 (1)	0.09 (1)*
H2n	0.255 (3)	0.885 (2)	0.729 (1)	0.06 (1)*
H4n	0.600 (3)	1.064 (1)	0.678 (1)	0.05 (1)*
H2	−0.0215	0.9256	0.5441	0.068*
H3	−0.3297	0.8223	0.5137	0.079*
H4	−0.4569	0.6911	0.6050	0.081*
H5	−0.2781	0.6703	0.7253	0.080*
H6	0.4505	0.8089	0.9121	0.079*
H7	0.7642	0.8682	0.9709	0.082*
H8	0.9727	1.0016	0.9044	0.082*
H9	0.8628	1.0675	0.7791	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0517 (3)	0.0755 (4)	0.0505 (3)	−0.0052 (3)	0.0030 (3)	0.0117 (3)
O1w	0.055 (1)	0.076 (1)	0.075 (1)	0.003 (1)	0.003 (1)	0.010 (1)
N1	0.045 (1)	0.052 (1)	0.069 (1)	−0.002 (1)	−0.002 (1)	0.008 (1)
N2	0.043 (1)	0.059 (1)	0.046 (1)	−0.004 (1)	−0.003 (1)	0.005 (1)
N3	0.052 (1)	0.066 (1)	0.049 (1)	−0.009 (1)	−0.003 (1)	0.002 (1)
N4	0.042 (1)	0.054 (1)	0.048 (1)	−0.006 (1)	0.002 (1)	−0.002 (1)
C1	0.036 (1)	0.047 (1)	0.054 (1)	0.004 (1)	0.003 (1)	−0.007 (1)
C2	0.055 (1)	0.062 (1)	0.053 (1)	−0.005 (1)	−0.004 (1)	0.000 (1)
C3	0.058 (1)	0.073 (1)	0.066 (1)	−0.001 (1)	−0.013 (1)	−0.006 (1)
C4	0.048 (1)	0.064 (1)	0.090 (2)	−0.009 (1)	−0.008 (1)	−0.003 (1)
C5	0.056 (2)	0.060 (1)	0.083 (2)	−0.011 (1)	−0.001 (1)	0.012 (1)
C6	0.069 (2)	0.075 (1)	0.054 (1)	−0.011 (1)	−0.003 (1)	0.007 (1)
C7	0.068 (2)	0.084 (2)	0.054 (1)	0.002 (1)	−0.015 (1)	0.003 (1)
C8	0.057 (1)	0.082 (2)	0.066 (1)	−0.006 (1)	−0.017 (1)	−0.010 (1)
C9	0.049 (1)	0.063 (1)	0.058 (1)	−0.008 (1)	−0.003 (1)	−0.006 (1)
C10	0.044 (1)	0.050 (1)	0.048 (1)	0.003 (1)	0.004 (1)	−0.009 (1)
C11	0.040 (1)	0.050 (1)	0.047 (1)	0.004 (1)	0.007 (1)	−0.006 (1)

Geometric parameters (Å, º)

S1—C11	1.688 (2)	C8—C9	1.378 (3)
N1—C5	1.339 (3)	C9—C10	1.394 (3)
N1—C1	1.346 (2)	O1w—H1w1	0.85 (1)
N2—C11	1.348 (3)	O1w—H1w2	0.84 (1)
N2—C1	1.408 (3)	N2—H2n	0.85 (1)
N3—C10	1.335 (3)	N4—H4n	0.84 (1)
N3—C6	1.354 (3)	C2—H2	0.93
N4—C11	1.381 (3)	C3—H3	0.93
N4—C10	1.412 (2)	C4—H4	0.93
C1—C2	1.390 (3)	C5—H5	0.93
C2—C3	1.388 (3)	C6—H6	0.93
C3—C4	1.371 (3)	C7—H7	0.93
C4—C5	1.376 (3)	C8—H8	0.93
C6—C7	1.369 (3)	C9—H9	0.93
C7—C8	1.385 (3)
C1—N1—C5	117.5 (2)	H1w1—O1w—H1w2	109 (3)
C11—N2—C1	132.8 (2)	C11—N2—H2n	113 (2)
C6—N3—C10	117.2 (2)	C1—N2—H2n	114 (2)
C10—N4—C11	131.0 (2)	C11—N4—H4n	114 (1)
N1—C1—C2	122.3 (2)	C10—N4—H4n	115 (1)
N1—C1—N2	110.8 (2)	C3—C2—H2	120.9
C2—C1—N2	126.9 (2)	C1—C2—H2	120.9
C1—C2—C3	118.2 (2)	C4—C3—H3	119.9
C2—C3—C4	120.3 (2)	C2—C3—H3	119.9
C3—C4—C5	117.5 (2)	C3—C4—H4	121.2
N1—C5—C4	124.3 (2)	C5—C4—H4	121.2
N3—C6—C7	123.7 (2)	N1—C5—H5	117.9
C6—C7—C8	118.0 (2)	C4—C5—H5	117.9
C7—C8—C9	119.9 (2)	N3—C6—H6	118.2
C8—C9—C10	118.0 (2)	C7—C6—H6	118.2
N3—C10—C9	123.1 (2)	C6—C7—H7	121.0
N3—C10—N4	118.6 (2)	C8—C7—H7	121.0
C9—C10—N4	118.3 (2)	C9—C8—H8	120.0
N2—C11—N4	115.2 (2)	C7—C8—H8	120.0
N2—C11—S1	126.9 (2)	C8—C9—H9	121.0
N4—C11—S1	117.9 (2)	C10—C9—H9	121.0
C5—N1—C1—C2	−0.5 (3)	C6—C7—C8—C9	−0.9 (4)
C5—N1—C1—N2	179.8 (2)	C7—C8—C9—C10	0.5 (3)
C11—N2—C1—N1	178.6 (2)	C6—N3—C10—C9	−0.9 (3)
C11—N2—C1—C2	−1.1 (3)	C6—N3—C10—N4	179.2 (2)
N1—C1—C2—C3	0.0 (3)	C8—C9—C10—N3	0.4 (3)
N2—C1—C2—C3	179.7 (2)	C8—C9—C10—N4	−179.7 (2)
C1—C2—C3—C4	−0.2 (3)	C11—N4—C10—N3	−2.4 (3)
C2—C3—C4—C5	0.8 (3)	C11—N4—C10—C9	177.7 (2)
C1—N1—C5—C4	1.1 (3)	C1—N2—C11—N4	−177.2 (2)
C3—C4—C5—N1	−1.2 (4)	C1—N2—C11—S1	3.5 (3)
C10—N3—C6—C7	0.5 (3)	C10—N4—C11—N2	0.1 (3)
N3—C6—C7—C8	0.4 (4)	C10—N4—C11—S1	179.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···N3	0.85 (1)	1.90 (2)	2.652 (2)	146 (2)
N4—H4n···O1w^i	0.84 (1)	2.19 (1)	3.016 (2)	166 (2)
O1w—H1w1···N1	0.85 (1)	2.18 (1)	3.008 (2)	166 (2)
O1w—H1w2···S1^ii	0.84 (1)	2.61 (1)	3.414 (2)	161 (2)

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x, y−1/2, −z+3/2.