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The structure of the title compound, C16H13N3S2, (I), consists of mol­ecules that associate via N—H...N and N—H...S interactions to form a linear one-dimensional hydrogen-bonded chain. The dihedral angles between the two phenyl rings and the pyrimidine ring are 74.94 (7) and 75.47 (7)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800017888/ob6001sup1.cif
Contains datablocks I, default

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536800017888/ob6001Isup2.hkl
Contains datablock I

CCDC reference: 155874

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.046
  • wR factor = 0.117
  • Data-to-parameter ratio = 17.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_420 Alert C D-H without acceptor N(21) - H(22) ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

NO COMMENT

Experimental top

The title compound, (I), was prepared by Spa Contract Synthesis. Crystals of (I) were grown from dmf/methanol(1/10) solution.

Refinement top

All H atoms were included in the refinement, at calculated positions, as riding models with C—H set to 0.95 Å (Ar—H), except for the amine H atoms, which were located on difference syntheses and both positional and thermal parameters refined.

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

2-Amino-4,6-bis(phenylthio)pyrimidine top
Crystal data top
C16H13N3S2F(000) = 648
Mr = 311.41Dx = 1.345 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.7937 (18) ÅCell parameters from 6016 reflections
b = 8.3091 (17) Åθ = 1.0–27.5°
c = 21.148 (4) ŵ = 0.34 mm1
β = 95.73 (3)°T = 150 K
V = 1537.5 (5) Å3Block, colourless
Z = 40.34 × 0.18 × 0.16 mm
Data collection top
Enraf Nonius KappaCCD area-detector
diffractometer
3476 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode2440 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.088
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 1.9°
ϕ and ω scansh = 1110
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
k = 910
Tmin = 0.893, Tmax = 0.947l = 2727
12370 measured reflections
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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0595P)2]
where P = (Fo2 + 2Fc2)/3
3476 reflections(Δ/σ)max = 0.009
198 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.47 e Å3
Crystal data top
C16H13N3S2V = 1537.5 (5) Å3
Mr = 311.41Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.7937 (18) ŵ = 0.34 mm1
b = 8.3091 (17) ÅT = 150 K
c = 21.148 (4) Å0.34 × 0.18 × 0.16 mm
β = 95.73 (3)°
Data collection top
Enraf Nonius KappaCCD area-detector
diffractometer
3476 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
2440 reflections with I > 2σ(I)
Tmin = 0.893, Tmax = 0.947Rint = 0.088
12370 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.29 e Å3
3476 reflectionsΔρmin = 0.47 e Å3
198 parameters
Special details top

Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

Geometry. Mean plane data ex SHELXL97 ###########################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 8.5612 (0.0048) x - 0.7071 (0.0071) y + 6.5153 (0.0178) z = 4.6782 (0.0045)

* -0.0065 (0.0013) C7 * -0.0020 (0.0015) C8 * 0.0066 (0.0016) C9 * -0.0026 (0.0016) C10 * -0.0060 (0.0015) C11 * 0.0106 (0.0014) C12

Rms deviation of fitted atoms = 0.0064

- 1.0656 (0.0061) x + 4.0487 (0.0060) y + 18.4531 (0.0125) z = 4.5647 (0.0047)

Angle to previous plane (with approximate e.s.d.) = 74.94 (0.07)

* 0.0056 (0.0012) N1 * -0.0113 (0.0013) C2 * 0.0060 (0.0012) N3 * 0.0041 (0.0013) C4 * -0.0090 (0.0012) C5 * 0.0046 (0.0012) C6

Rms deviation of fitted atoms = 0.0072

8.7084 (0.0047) x - 0.2201 (0.0064) y - 4.9597 (0.0157) z = 0.1054 (0.0034)

Angle to previous plane (with approximate e.s.d.) = 75.47 (0.07)

* -0.0031 (0.0012) C13 * 0.0052 (0.0013) C14 * -0.0031 (0.0013) C15 * -0.0009 (0.0015) C16 * 0.0030 (0.0015) C17 * -0.0009 (0.0013) C18

Rms deviation of fitted atoms = 0.0031

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.11796 (16)0.86840 (19)0.05032 (7)0.0250 (4)
C20.2636 (2)0.9113 (2)0.03158 (9)0.0263 (4)
N210.2840 (2)1.0482 (2)0.00121 (9)0.0377 (5)
H210.367 (3)1.078 (3)0.0130 (11)0.046 (7)*
H220.195 (2)1.096 (3)0.0085 (10)0.045 (7)*
N30.38907 (16)0.82762 (19)0.04364 (7)0.0277 (4)
C40.3641 (2)0.6896 (2)0.07527 (8)0.0243 (4)
C50.21929 (18)0.6316 (2)0.09563 (8)0.0225 (4)
H50.20330.53220.11750.028*
C60.09983 (19)0.7301 (2)0.08166 (8)0.0219 (4)
S10.53545 (5)0.59059 (7)0.08775 (3)0.0405 (2)
C70.47507 (19)0.4307 (2)0.13952 (9)0.0263 (4)
C80.4799 (2)0.2752 (3)0.11697 (11)0.0407 (5)
H80.51100.25440.07340.051*
C90.4391 (3)0.1490 (3)0.15819 (13)0.0524 (7)
H90.44330.04140.14290.065*
C100.3931 (2)0.1792 (3)0.22057 (12)0.0480 (6)
H100.36420.09240.24850.060*
C110.3881 (3)0.3333 (3)0.24326 (11)0.0451 (6)
H110.35520.35350.28670.056*
C120.4314 (2)0.4599 (3)0.20276 (10)0.0364 (5)
H120.43080.56680.21870.045*
S20.09499 (5)0.69097 (6)0.10351 (2)0.02865 (17)
C130.09830 (18)0.4884 (2)0.13030 (9)0.0230 (4)
C140.0717 (2)0.3629 (3)0.08753 (9)0.0302 (5)
H140.04850.38500.04350.038*
C150.0789 (2)0.2053 (3)0.10885 (10)0.0343 (5)
H150.05930.11900.07970.043*
C160.1147 (2)0.1744 (3)0.17267 (10)0.0357 (5)
H160.12030.06630.18740.045*
C170.1425 (2)0.2983 (3)0.21503 (10)0.0387 (5)
H170.16750.27570.25890.048*
C180.1342 (2)0.4560 (3)0.19428 (9)0.0299 (5)
H180.15300.54170.22370.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0262 (8)0.0199 (9)0.0286 (9)0.0012 (6)0.0017 (6)0.0019 (7)
C20.0319 (11)0.0210 (11)0.0263 (10)0.0065 (8)0.0036 (8)0.0042 (8)
N210.0350 (11)0.0288 (11)0.0489 (12)0.0064 (9)0.0029 (9)0.0172 (9)
N30.0240 (8)0.0269 (10)0.0324 (9)0.0066 (7)0.0033 (7)0.0086 (7)
C40.0236 (10)0.0251 (11)0.0243 (10)0.0030 (7)0.0037 (7)0.0049 (8)
C50.0210 (9)0.0213 (10)0.0251 (10)0.0032 (7)0.0013 (7)0.0056 (8)
C60.0219 (9)0.0222 (11)0.0216 (10)0.0049 (7)0.0023 (7)0.0000 (8)
S10.0180 (3)0.0464 (4)0.0569 (4)0.0036 (2)0.0030 (2)0.0258 (3)
C70.0178 (9)0.0294 (12)0.0322 (11)0.0019 (8)0.0045 (7)0.0087 (9)
C80.0431 (13)0.0414 (15)0.0374 (13)0.0001 (10)0.0024 (9)0.0034 (11)
C90.0602 (16)0.0285 (14)0.0694 (19)0.0039 (11)0.0112 (13)0.0011 (13)
C100.0408 (13)0.0454 (17)0.0579 (17)0.0075 (11)0.0060 (11)0.0268 (13)
C110.0425 (13)0.0588 (18)0.0339 (13)0.0049 (11)0.0036 (10)0.0152 (12)
C120.0378 (12)0.0355 (14)0.0370 (13)0.0040 (9)0.0098 (9)0.0010 (10)
S20.0187 (3)0.0248 (3)0.0419 (3)0.00065 (18)0.0004 (2)0.0068 (2)
C130.0147 (9)0.0228 (11)0.0313 (11)0.0011 (7)0.0020 (7)0.0023 (8)
C140.0315 (11)0.0301 (12)0.0284 (11)0.0042 (8)0.0006 (8)0.0002 (9)
C150.0369 (12)0.0275 (12)0.0376 (13)0.0029 (9)0.0002 (9)0.0059 (10)
C160.0408 (12)0.0241 (13)0.0418 (13)0.0027 (9)0.0027 (9)0.0068 (10)
C170.0509 (14)0.0362 (14)0.0277 (12)0.0051 (10)0.0016 (9)0.0077 (10)
C180.0294 (10)0.0275 (12)0.0317 (12)0.0033 (8)0.0025 (8)0.0029 (9)
Geometric parameters (Å, º) top
N1—C61.328 (2)C9—H90.9500
N1—C21.350 (2)C10—C111.366 (3)
C2—N211.335 (3)C10—H100.9500
C2—N31.350 (2)C11—C121.386 (3)
N21—H210.78 (2)C11—H110.9500
N21—H220.90 (2)C12—H120.9500
N3—C41.335 (2)S2—C131.775 (2)
C4—C51.389 (2)C13—C141.385 (3)
C4—S11.7593 (18)C13—C181.385 (3)
C5—C61.387 (2)C14—C151.384 (3)
C5—H50.9500C14—H140.9500
C6—S21.7596 (18)C15—C161.379 (3)
S1—C71.7693 (19)C15—H150.9500
C7—C81.376 (3)C16—C171.371 (3)
C7—C121.376 (3)C16—H160.9500
C8—C91.388 (3)C17—C181.381 (3)
C8—H80.9500C17—H170.9500
C9—C101.364 (3)C18—H180.9500
C6—N1—C2115.99 (15)C9—C10—H10119.7
N21—C2—N3117.86 (18)C11—C10—H10119.7
N21—C2—N1116.86 (18)C10—C11—C12119.8 (2)
N3—C2—N1125.28 (17)C10—C11—H11120.1
C2—N21—H21120.3 (18)C12—C11—H11120.1
C2—N21—H22113.2 (15)C7—C12—C11120.0 (2)
H21—N21—H22127 (2)C7—C12—H12120.0
C4—N3—C2116.17 (15)C11—C12—H12120.0
N3—C4—C5123.56 (16)C6—S2—C13104.10 (8)
N3—C4—S1112.12 (13)C14—C13—C18119.90 (18)
C5—C4—S1124.32 (14)C14—C13—S2120.60 (15)
C6—C5—C4114.83 (17)C18—C13—S2119.44 (15)
C6—C5—H5122.6C15—C14—C13120.02 (19)
C4—C5—H5122.6C15—C14—H14120.0
N1—C6—C5124.14 (16)C13—C14—H14120.0
N1—C6—S2110.87 (13)C16—C15—C14119.6 (2)
C5—C6—S2124.99 (14)C16—C15—H15120.2
C4—S1—C7103.61 (9)C14—C15—H15120.2
C8—C7—C12119.90 (19)C17—C16—C15120.5 (2)
C8—C7—S1119.57 (16)C17—C16—H16119.7
C12—C7—S1120.43 (16)C15—C16—H16119.7
C7—C8—C9119.6 (2)C16—C17—C18120.3 (2)
C7—C8—H8120.2C16—C17—H17119.8
C9—C8—H8120.2C18—C17—H17119.8
C10—C9—C8120.1 (2)C17—C18—C13119.67 (19)
C10—C9—H9119.9C17—C18—H18120.2
C8—C9—H9119.9C13—C18—H18120.2
C9—C10—C11120.5 (2)
C6—N1—C2—N21178.56 (18)C7—C8—C9—C100.6 (3)
C6—N1—C2—N31.8 (3)C8—C9—C10—C110.7 (4)
N21—C2—N3—C4178.52 (18)C9—C10—C11—C120.5 (3)
N1—C2—N3—C41.8 (3)C8—C7—C12—C111.8 (3)
C2—N3—C4—C50.3 (3)S1—C7—C12—C11178.29 (16)
C2—N3—C4—S1179.60 (14)C10—C11—C12—C71.8 (3)
N3—C4—C5—C61.1 (3)N1—C6—S2—C13169.17 (13)
S1—C4—C5—C6179.02 (14)C5—C6—S2—C1311.49 (18)
C2—N1—C6—C50.2 (3)C6—S2—C13—C1472.38 (16)
C2—N1—C6—S2179.51 (13)C6—S2—C13—C18110.35 (15)
C4—C5—C6—N11.2 (3)C18—C13—C14—C150.9 (3)
C4—C5—C6—S2178.06 (14)S2—C13—C14—C15178.16 (14)
N3—C4—S1—C7171.71 (14)C13—C14—C15—C160.9 (3)
C5—C4—S1—C78.43 (19)C14—C15—C16—C170.3 (3)
C4—S1—C7—C8108.49 (16)C15—C16—C17—C180.3 (3)
C4—S1—C7—C1275.05 (17)C16—C17—C18—C130.3 (3)
C12—C7—C8—C90.6 (3)C14—C13—C18—C170.3 (3)
S1—C7—C8—C9177.11 (16)S2—C13—C18—C17177.61 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21—H21···N3i0.78 (2)2.32 (2)3.102 (2)177 (2)
N21—H22···S2ii0.90 (2)2.88 (2)3.586 (2)136.2 (17)
Symmetry codes: (i) x1, y+2, z; (ii) x, y+2, z.

Experimental details

Crystal data
Chemical formulaC16H13N3S2
Mr311.41
Crystal system, space groupMonoclinic, P21/n
Temperature (K)150
a, b, c (Å)8.7937 (18), 8.3091 (17), 21.148 (4)
β (°) 95.73 (3)
V3)1537.5 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.34
Crystal size (mm)0.34 × 0.18 × 0.16
Data collection
DiffractometerEnraf Nonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1995)
Tmin, Tmax0.893, 0.947
No. of measured, independent and
observed [I > 2σ(I)] reflections
12370, 3476, 2440
Rint0.088
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.117, 1.00
No. of reflections3476
No. of parameters198
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.29, 0.47

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21—H21···N3i0.78 (2)2.32 (2)3.102 (2)177 (2)
N21—H22···S2ii0.90 (2)2.88 (2)3.586 (2)136.2 (17)
Symmetry codes: (i) x1, y+2, z; (ii) x, y+2, z.
 

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