Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807019459/hg2229sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807019459/hg2229Isup2.hkl |
CCDC reference: 647689
Freshly prepared pivaloylisothiocyanate (1.43 g, 10 mmol) in acetone (30 ml) was stirred for 30 minutes. Neat 2-aminopyrimidine (1.0 g, 10 mmol) was then added and the resulting mixture was stirred for 1 h. The reaction mixture was poured into acidified water and stirred well. The solid product was separated and washed with deionized water and purified by recrystallization from methanol/ chloroform (1:5 v/v) to give fine crystals of (I), with an overall yield of 80%.
C-bound H atoms were included in the riding model approximation with C—H 0.95–0.98 Å, and with Uiso(H) = 1.2 Ueq(C) or Uiso(H) = 1.5 Ueq(Cmethyl). The N-bound H atoms were refined isotropically.
The background to this study has been set out in our previous work for the structural chemistry of N,N'-disubstituted thioureas (Shoukat et al., 2007). Herein, as a continuation of these studies, the structure of the title compound (I) is described. A depiction of the molecule is given in Fig. 1. Bond lengths and angles, see the selected geometric parameters table, can be regarded as typical for N,N'-disubstituted thiourea compounds as found in the Cambridge Structural Database v5.28 (Allen, 2002; Khawar Rauf et al., 2006). The molecule exists in its thione form with typical thiourea C—S and C—O bond distances, as well as shortened C—N bonds (See geometric parameters table). The planes containing the S1, O1, N1, N2, C1 & C2 and S2, O2, N5, N6, C11 & C12 atoms are almost parallel to the pyrimidine ring, forming dihedral angles of 9.54 (13)° and 12.92 (12)° respectively. The molecules also feature intra & intermolecular N—H···N hydrogen bonds (See hydrogen-bond geometry table and Fig 2).
For related literature, see: Allen (2002); Khawar Rauf, Badshah & Flörke (2006); Shoukat et al. (2007).
Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001); cell refinement: CrystalClear; data reduction: TEXSAN (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 and TEXSAN.
C10H14N4OS | Z = 4 |
Mr = 238.31 | F(000) = 504 |
Triclinic, P1 | Dx = 1.357 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71070 Å |
a = 5.652 (3) Å | Cell parameters from 3112 reflections |
b = 11.674 (8) Å | θ = 3.3–27.5° |
c = 18.585 (12) Å | µ = 0.26 mm−1 |
α = 106.915 (9)° | T = 113 K |
β = 92.642 (6)° | Block, yellow |
γ = 94.478 (8)° | 0.45 × 0.36 × 0.20 mm |
V = 1166.6 (13) Å3 |
Rigaku/MSC Mercury CCD diffractometer | 4314 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.034 |
Graphite monochromator | θmax = 27.5°, θmin = 3.3° |
Detector resolution: 14.62 pixels mm-1 | h = −7→7 |
ω scans | k = −15→9 |
9547 measured reflections | l = −18→24 |
5309 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0286P)2 + 1.3663P] where P = (Fo2 + 2Fc2)/3 |
5309 reflections | (Δ/σ)max < 0.001 |
311 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
C10H14N4OS | γ = 94.478 (8)° |
Mr = 238.31 | V = 1166.6 (13) Å3 |
Triclinic, P1 | Z = 4 |
a = 5.652 (3) Å | Mo Kα radiation |
b = 11.674 (8) Å | µ = 0.26 mm−1 |
c = 18.585 (12) Å | T = 113 K |
α = 106.915 (9)° | 0.45 × 0.36 × 0.20 mm |
β = 92.642 (6)° |
Rigaku/MSC Mercury CCD diffractometer | 4314 reflections with I > 2σ(I) |
9547 measured reflections | Rint = 0.034 |
5309 independent reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.118 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρmax = 0.33 e Å−3 |
5309 reflections | Δρmin = −0.32 e Å−3 |
311 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.0618 (4) | 0.4642 (2) | 0.17088 (13) | 0.0190 (5) | |
S1 | −0.17984 (11) | 0.37188 (6) | 0.16735 (4) | 0.02662 (16) | |
N1 | 0.1016 (3) | 0.50531 (18) | 0.10978 (11) | 0.0197 (4) | |
H1 | −0.010 (5) | 0.480 (3) | 0.0741 (17) | 0.032 (8)* | |
C2 | 0.2483 (4) | 0.4715 (2) | 0.29593 (13) | 0.0199 (5) | |
O1 | 0.1185 (3) | 0.39231 (16) | 0.30699 (10) | 0.0307 (4) | |
N2 | 0.2299 (4) | 0.50592 (18) | 0.23032 (11) | 0.0199 (4) | |
H2 | 0.339 (5) | 0.555 (3) | 0.2231 (16) | 0.029 (8)* | |
C3 | 0.2906 (4) | 0.5791 (2) | 0.09625 (13) | 0.0177 (5) | |
N3 | 0.4638 (3) | 0.62528 (18) | 0.15060 (11) | 0.0214 (4) | |
C4 | 0.6480 (4) | 0.6896 (2) | 0.13348 (14) | 0.0228 (5) | |
H4A | 0.7752 | 0.7240 | 0.1706 | 0.027* | |
C5 | 0.6579 (4) | 0.7071 (2) | 0.06343 (14) | 0.0231 (5) | |
H5A | 0.7910 | 0.7504 | 0.0509 | 0.028* | |
C6 | 0.4640 (4) | 0.6585 (2) | 0.01227 (13) | 0.0221 (5) | |
H6A | 0.4640 | 0.6714 | −0.0359 | 0.026* | |
N4 | 0.2768 (3) | 0.59406 (18) | 0.02747 (11) | 0.0206 (4) | |
C7 | 0.4417 (4) | 0.5426 (2) | 0.35636 (13) | 0.0217 (5) | |
C8 | 0.6106 (5) | 0.6306 (2) | 0.33193 (15) | 0.0302 (6) | |
H8A | 0.6919 | 0.5865 | 0.2884 | 0.045* | |
H8B | 0.7285 | 0.6716 | 0.3736 | 0.045* | |
H8C | 0.5197 | 0.6902 | 0.3181 | 0.045* | |
C9 | 0.3076 (5) | 0.6119 (3) | 0.42255 (15) | 0.0338 (6) | |
H9A | 0.4220 | 0.6566 | 0.4644 | 0.051* | |
H9B | 0.2020 | 0.5552 | 0.4390 | 0.051* | |
H9C | 0.2130 | 0.6683 | 0.4066 | 0.051* | |
C10 | 0.5839 (5) | 0.4511 (3) | 0.37960 (17) | 0.0340 (6) | |
H10A | 0.6701 | 0.4078 | 0.3370 | 0.051* | |
H10B | 0.4748 | 0.3938 | 0.3944 | 0.051* | |
H10C | 0.6976 | 0.4932 | 0.4223 | 0.051* | |
C11 | 0.2873 (4) | −0.0628 (2) | 0.32001 (13) | 0.0194 (5) | |
S2 | 0.05219 (11) | −0.15886 (6) | 0.31716 (3) | 0.02635 (16) | |
N5 | 0.4319 (3) | −0.01896 (18) | 0.38563 (11) | 0.0200 (4) | |
H5 | 0.386 (5) | −0.041 (2) | 0.4230 (16) | 0.021 (7)* | |
C12 | 0.2599 (4) | −0.0515 (2) | 0.18742 (13) | 0.0187 (5) | |
O2 | 0.1185 (3) | −0.13758 (16) | 0.15963 (10) | 0.0265 (4) | |
N6 | 0.3540 (4) | −0.01990 (19) | 0.26246 (11) | 0.0228 (5) | |
H6 | 0.470 (6) | 0.037 (3) | 0.2758 (18) | 0.043 (9)* | |
C13 | 0.6386 (4) | 0.0593 (2) | 0.40249 (13) | 0.0187 (5) | |
N7 | 0.7068 (4) | 0.11528 (18) | 0.35241 (11) | 0.0219 (4) | |
C14 | 0.9128 (4) | 0.1856 (2) | 0.37013 (14) | 0.0238 (5) | |
H14A | 0.9672 | 0.2270 | 0.3360 | 0.029* | |
C15 | 1.0473 (4) | 0.1998 (2) | 0.43597 (14) | 0.0243 (5) | |
H15A | 1.1957 | 0.2478 | 0.4474 | 0.029* | |
C16 | 0.9569 (4) | 0.1409 (2) | 0.48524 (14) | 0.0232 (5) | |
H16A | 1.0452 | 0.1504 | 0.5317 | 0.028* | |
N8 | 0.7501 (3) | 0.07114 (18) | 0.46991 (11) | 0.0210 (4) | |
C17 | 0.3594 (4) | 0.0349 (2) | 0.14560 (13) | 0.0198 (5) | |
C18 | 0.2489 (5) | −0.0087 (3) | 0.06439 (14) | 0.0295 (6) | |
H18A | 0.0753 | −0.0106 | 0.0646 | 0.044* | |
H18B | 0.2931 | −0.0896 | 0.0398 | 0.044* | |
H18C | 0.3076 | 0.0463 | 0.0368 | 0.044* | |
C19 | 0.6315 (4) | 0.0367 (2) | 0.14566 (14) | 0.0233 (5) | |
H19A | 0.6913 | 0.0878 | 0.1157 | 0.035* | |
H19B | 0.6749 | −0.0453 | 0.1238 | 0.035* | |
H19C | 0.7021 | 0.0687 | 0.1976 | 0.035* | |
C20 | 0.2929 (4) | 0.1612 (2) | 0.18413 (15) | 0.0262 (5) | |
H20A | 0.3465 | 0.2154 | 0.1553 | 0.039* | |
H20B | 0.3696 | 0.1900 | 0.2354 | 0.039* | |
H20C | 0.1198 | 0.1593 | 0.1865 | 0.039* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0185 (11) | 0.0198 (11) | 0.0187 (12) | 0.0015 (9) | −0.0006 (9) | 0.0061 (9) |
S1 | 0.0229 (3) | 0.0307 (3) | 0.0262 (3) | −0.0091 (3) | −0.0049 (2) | 0.0124 (3) |
N1 | 0.0176 (10) | 0.0227 (10) | 0.0183 (10) | −0.0048 (8) | −0.0051 (8) | 0.0080 (8) |
C2 | 0.0215 (11) | 0.0200 (11) | 0.0175 (11) | 0.0007 (9) | 0.0019 (9) | 0.0048 (9) |
O1 | 0.0358 (10) | 0.0309 (10) | 0.0266 (10) | −0.0112 (8) | −0.0034 (8) | 0.0151 (8) |
N2 | 0.0199 (10) | 0.0208 (10) | 0.0191 (10) | −0.0050 (8) | −0.0024 (8) | 0.0084 (8) |
C3 | 0.0166 (10) | 0.0170 (11) | 0.0185 (11) | −0.0009 (9) | −0.0024 (9) | 0.0048 (9) |
N3 | 0.0214 (10) | 0.0226 (10) | 0.0195 (10) | −0.0044 (8) | −0.0051 (8) | 0.0079 (8) |
C4 | 0.0200 (11) | 0.0226 (12) | 0.0247 (13) | −0.0030 (9) | −0.0041 (10) | 0.0074 (10) |
C5 | 0.0202 (12) | 0.0233 (12) | 0.0250 (13) | −0.0056 (10) | −0.0023 (10) | 0.0082 (10) |
C6 | 0.0254 (12) | 0.0240 (12) | 0.0168 (12) | −0.0017 (10) | −0.0010 (9) | 0.0076 (10) |
N4 | 0.0204 (10) | 0.0211 (10) | 0.0196 (10) | −0.0024 (8) | −0.0018 (8) | 0.0064 (8) |
C7 | 0.0204 (11) | 0.0259 (12) | 0.0192 (12) | −0.0004 (10) | −0.0016 (9) | 0.0081 (10) |
C8 | 0.0297 (13) | 0.0345 (15) | 0.0257 (14) | −0.0107 (11) | −0.0079 (11) | 0.0128 (12) |
C9 | 0.0361 (15) | 0.0399 (16) | 0.0205 (13) | 0.0007 (12) | −0.0014 (11) | 0.0023 (12) |
C10 | 0.0252 (13) | 0.0451 (17) | 0.0395 (17) | 0.0043 (12) | −0.0023 (12) | 0.0249 (14) |
C11 | 0.0205 (11) | 0.0211 (11) | 0.0162 (11) | −0.0020 (9) | −0.0018 (9) | 0.0063 (9) |
S2 | 0.0259 (3) | 0.0327 (3) | 0.0196 (3) | −0.0122 (3) | −0.0041 (2) | 0.0112 (3) |
N5 | 0.0212 (10) | 0.0236 (10) | 0.0163 (10) | −0.0053 (8) | −0.0017 (8) | 0.0098 (8) |
C12 | 0.0164 (11) | 0.0247 (12) | 0.0148 (11) | 0.0019 (9) | 0.0015 (9) | 0.0057 (9) |
O2 | 0.0268 (9) | 0.0295 (10) | 0.0202 (9) | −0.0101 (8) | −0.0032 (7) | 0.0065 (7) |
N6 | 0.0239 (11) | 0.0258 (11) | 0.0184 (10) | −0.0089 (9) | −0.0041 (8) | 0.0101 (9) |
C13 | 0.0204 (11) | 0.0189 (11) | 0.0159 (11) | −0.0014 (9) | −0.0002 (9) | 0.0048 (9) |
N7 | 0.0240 (10) | 0.0233 (10) | 0.0182 (10) | −0.0054 (8) | −0.0015 (8) | 0.0084 (8) |
C14 | 0.0269 (12) | 0.0230 (12) | 0.0215 (12) | −0.0029 (10) | 0.0026 (10) | 0.0077 (10) |
C15 | 0.0231 (12) | 0.0237 (12) | 0.0238 (13) | −0.0065 (10) | 0.0004 (10) | 0.0062 (10) |
C16 | 0.0236 (12) | 0.0230 (12) | 0.0205 (12) | −0.0018 (10) | −0.0021 (9) | 0.0040 (10) |
N8 | 0.0209 (10) | 0.0236 (10) | 0.0178 (10) | −0.0011 (8) | −0.0013 (8) | 0.0064 (8) |
C17 | 0.0156 (11) | 0.0269 (12) | 0.0186 (12) | −0.0002 (9) | −0.0008 (9) | 0.0105 (10) |
C18 | 0.0251 (13) | 0.0475 (16) | 0.0176 (12) | −0.0026 (12) | −0.0007 (10) | 0.0143 (12) |
C19 | 0.0187 (11) | 0.0300 (13) | 0.0226 (13) | 0.0019 (10) | 0.0014 (9) | 0.0102 (10) |
C20 | 0.0248 (12) | 0.0291 (13) | 0.0291 (14) | 0.0033 (10) | 0.0041 (10) | 0.0148 (11) |
C1—N2 | 1.371 (3) | C11—N6 | 1.362 (3) |
C1—N1 | 1.376 (3) | C11—N5 | 1.377 (3) |
C1—S1 | 1.659 (2) | C11—S2 | 1.659 (2) |
N1—C3 | 1.397 (3) | N5—C13 | 1.390 (3) |
N1—H1 | 0.86 (3) | N5—H5 | 0.85 (3) |
C2—O1 | 1.206 (3) | C12—O2 | 1.204 (3) |
C2—N2 | 1.392 (3) | C12—N6 | 1.402 (3) |
C2—C7 | 1.532 (3) | C12—C17 | 1.531 (3) |
N2—H2 | 0.85 (3) | N6—H6 | 0.86 (3) |
C3—N3 | 1.334 (3) | C13—N7 | 1.338 (3) |
C3—N4 | 1.339 (3) | C13—N8 | 1.341 (3) |
N3—C4 | 1.340 (3) | N7—C14 | 1.340 (3) |
C4—C5 | 1.378 (3) | C14—C15 | 1.371 (4) |
C4—H4A | 0.9500 | C14—H14A | 0.9500 |
C5—C6 | 1.385 (3) | C15—C16 | 1.388 (3) |
C5—H5A | 0.9500 | C15—H15A | 0.9500 |
C6—N4 | 1.338 (3) | C16—N8 | 1.340 (3) |
C6—H6A | 0.9500 | C16—H16A | 0.9500 |
C7—C8 | 1.527 (3) | C17—C20 | 1.525 (4) |
C7—C10 | 1.531 (4) | C17—C18 | 1.531 (3) |
C7—C9 | 1.531 (4) | C17—C19 | 1.537 (3) |
C8—H8A | 0.9800 | C18—H18A | 0.9800 |
C8—H8B | 0.9800 | C18—H18B | 0.9800 |
C8—H8C | 0.9800 | C18—H18C | 0.9800 |
C9—H9A | 0.9800 | C19—H19A | 0.9800 |
C9—H9B | 0.9800 | C19—H19B | 0.9800 |
C9—H9C | 0.9800 | C19—H19C | 0.9800 |
C10—H10A | 0.9800 | C20—H20A | 0.9800 |
C10—H10B | 0.9800 | C20—H20B | 0.9800 |
C10—H10C | 0.9800 | C20—H20C | 0.9800 |
N2—C1—N1 | 115.3 (2) | N6—C11—N5 | 114.8 (2) |
N2—C1—S1 | 125.97 (18) | N6—C11—S2 | 125.95 (18) |
N1—C1—S1 | 118.74 (17) | N5—C11—S2 | 119.27 (17) |
C1—N1—C3 | 131.0 (2) | C11—N5—C13 | 130.8 (2) |
C1—N1—H1 | 113.4 (19) | C11—N5—H5 | 115.6 (18) |
C3—N1—H1 | 115.6 (19) | C13—N5—H5 | 113.6 (18) |
O1—C2—N2 | 123.3 (2) | O2—C12—N6 | 123.2 (2) |
O1—C2—C7 | 120.3 (2) | O2—C12—C17 | 124.5 (2) |
N2—C2—C7 | 116.36 (19) | N6—C12—C17 | 112.29 (19) |
C1—N2—C2 | 127.9 (2) | C11—N6—C12 | 129.9 (2) |
C1—N2—H2 | 113.3 (19) | C11—N6—H6 | 113 (2) |
C2—N2—H2 | 118.6 (19) | C12—N6—H6 | 117 (2) |
N3—C3—N4 | 126.9 (2) | N7—C13—N8 | 126.4 (2) |
N3—C3—N1 | 118.6 (2) | N7—C13—N5 | 119.0 (2) |
N4—C3—N1 | 114.45 (19) | N8—C13—N5 | 114.59 (19) |
C3—N3—C4 | 116.5 (2) | C13—N7—C14 | 116.5 (2) |
N3—C4—C5 | 121.8 (2) | N7—C14—C15 | 122.1 (2) |
N3—C4—H4A | 119.1 | N7—C14—H14A | 119.0 |
C5—C4—H4A | 119.1 | C15—C14—H14A | 119.0 |
C4—C5—C6 | 116.7 (2) | C14—C15—C16 | 117.0 (2) |
C4—C5—H5A | 121.6 | C14—C15—H15A | 121.5 |
C6—C5—H5A | 121.6 | C16—C15—H15A | 121.5 |
N4—C6—C5 | 123.1 (2) | N8—C16—C15 | 122.7 (2) |
N4—C6—H6A | 118.4 | N8—C16—H16A | 118.7 |
C5—C6—H6A | 118.4 | C15—C16—H16A | 118.7 |
C6—N4—C3 | 114.94 (19) | C16—N8—C13 | 115.3 (2) |
C8—C7—C10 | 109.6 (2) | C20—C17—C18 | 109.8 (2) |
C8—C7—C9 | 109.5 (2) | C20—C17—C12 | 109.4 (2) |
C10—C7—C9 | 110.1 (2) | C18—C17—C12 | 108.02 (19) |
C8—C7—C2 | 114.9 (2) | C20—C17—C19 | 109.41 (19) |
C10—C7—C2 | 107.3 (2) | C18—C17—C19 | 109.7 (2) |
C9—C7—C2 | 105.3 (2) | C12—C17—C19 | 110.48 (19) |
C7—C8—H8A | 109.5 | C17—C18—H18A | 109.5 |
C7—C8—H8B | 109.5 | C17—C18—H18B | 109.5 |
H8A—C8—H8B | 109.5 | H18A—C18—H18B | 109.5 |
C7—C8—H8C | 109.5 | C17—C18—H18C | 109.5 |
H8A—C8—H8C | 109.5 | H18A—C18—H18C | 109.5 |
H8B—C8—H8C | 109.5 | H18B—C18—H18C | 109.5 |
C7—C9—H9A | 109.5 | C17—C19—H19A | 109.5 |
C7—C9—H9B | 109.5 | C17—C19—H19B | 109.5 |
H9A—C9—H9B | 109.5 | H19A—C19—H19B | 109.5 |
C7—C9—H9C | 109.5 | C17—C19—H19C | 109.5 |
H9A—C9—H9C | 109.5 | H19A—C19—H19C | 109.5 |
H9B—C9—H9C | 109.5 | H19B—C19—H19C | 109.5 |
C7—C10—H10A | 109.5 | C17—C20—H20A | 109.5 |
C7—C10—H10B | 109.5 | C17—C20—H20B | 109.5 |
H10A—C10—H10B | 109.5 | H20A—C20—H20B | 109.5 |
C7—C10—H10C | 109.5 | C17—C20—H20C | 109.5 |
H10A—C10—H10C | 109.5 | H20A—C20—H20C | 109.5 |
H10B—C10—H10C | 109.5 | H20B—C20—H20C | 109.5 |
N2—C1—N1—C3 | 3.1 (4) | N6—C11—N5—C13 | −2.0 (4) |
S1—C1—N1—C3 | −177.5 (2) | S2—C11—N5—C13 | 178.7 (2) |
N1—C1—N2—C2 | −173.5 (2) | N5—C11—N6—C12 | 174.7 (2) |
S1—C1—N2—C2 | 7.1 (4) | S2—C11—N6—C12 | −6.0 (4) |
O1—C2—N2—C1 | 4.1 (4) | O2—C12—N6—C11 | −10.9 (4) |
C7—C2—N2—C1 | −174.2 (2) | C17—C12—N6—C11 | 169.7 (2) |
C1—N1—C3—N3 | −3.5 (4) | C11—N5—C13—N7 | 8.3 (4) |
C1—N1—C3—N4 | 175.7 (2) | C11—N5—C13—N8 | −172.2 (2) |
N4—C3—N3—C4 | −2.9 (4) | N8—C13—N7—C14 | 3.4 (4) |
N1—C3—N3—C4 | 176.2 (2) | N5—C13—N7—C14 | −177.2 (2) |
C3—N3—C4—C5 | 0.1 (4) | C13—N7—C14—C15 | 0.0 (4) |
N3—C4—C5—C6 | 2.1 (4) | N7—C14—C15—C16 | −2.1 (4) |
C4—C5—C6—N4 | −2.0 (4) | C14—C15—C16—N8 | 1.1 (4) |
C5—C6—N4—C3 | −0.4 (4) | C15—C16—N8—C13 | 1.8 (4) |
N3—C3—N4—C6 | 3.0 (4) | N7—C13—N8—C16 | −4.2 (4) |
N1—C3—N4—C6 | −176.1 (2) | N5—C13—N8—C16 | 176.3 (2) |
O1—C2—C7—C8 | 173.6 (2) | O2—C12—C17—C20 | 119.2 (3) |
N2—C2—C7—C8 | −8.0 (3) | N6—C12—C17—C20 | −61.4 (3) |
O1—C2—C7—C10 | 51.5 (3) | O2—C12—C17—C18 | −0.3 (3) |
N2—C2—C7—C10 | −130.1 (2) | N6—C12—C17—C18 | 179.1 (2) |
O1—C2—C7—C9 | −65.8 (3) | O2—C12—C17—C19 | −120.3 (3) |
N2—C2—C7—C9 | 112.6 (2) | N6—C12—C17—C19 | 59.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N4i | 0.86 (3) | 2.27 (3) | 3.133 (3) | 174 (3) |
N2—H2···N3 | 0.85 (3) | 1.90 (3) | 2.642 (3) | 144 (3) |
N5—H5···N8ii | 0.85 (3) | 2.28 (3) | 3.122 (3) | 171 (2) |
N6—H6···N7 | 0.86 (3) | 1.88 (3) | 2.632 (3) | 144 (3) |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C10H14N4OS |
Mr | 238.31 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 113 |
a, b, c (Å) | 5.652 (3), 11.674 (8), 18.585 (12) |
α, β, γ (°) | 106.915 (9), 92.642 (6), 94.478 (8) |
V (Å3) | 1166.6 (13) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.26 |
Crystal size (mm) | 0.45 × 0.36 × 0.20 |
Data collection | |
Diffractometer | Rigaku/MSC Mercury CCD |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9547, 5309, 4314 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.118, 1.10 |
No. of reflections | 5309 |
No. of parameters | 311 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.33, −0.32 |
Computer programs: CrystalClear (Molecular Structure Corporation & Rigaku, 2001), CrystalClear, TEXSAN (Rigaku/MSC, 2004), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97 and TEXSAN.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N4i | 0.86 (3) | 2.27 (3) | 3.133 (3) | 174 (3) |
N2—H2···N3 | 0.85 (3) | 1.90 (3) | 2.642 (3) | 144 (3) |
N5—H5···N8ii | 0.85 (3) | 2.28 (3) | 3.122 (3) | 171 (2) |
N6—H6···N7 | 0.86 (3) | 1.88 (3) | 2.632 (3) | 144 (3) |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y, −z+1. |
The background to this study has been set out in our previous work for the structural chemistry of N,N'-disubstituted thioureas (Shoukat et al., 2007). Herein, as a continuation of these studies, the structure of the title compound (I) is described. A depiction of the molecule is given in Fig. 1. Bond lengths and angles, see the selected geometric parameters table, can be regarded as typical for N,N'-disubstituted thiourea compounds as found in the Cambridge Structural Database v5.28 (Allen, 2002; Khawar Rauf et al., 2006). The molecule exists in its thione form with typical thiourea C—S and C—O bond distances, as well as shortened C—N bonds (See geometric parameters table). The planes containing the S1, O1, N1, N2, C1 & C2 and S2, O2, N5, N6, C11 & C12 atoms are almost parallel to the pyrimidine ring, forming dihedral angles of 9.54 (13)° and 12.92 (12)° respectively. The molecules also feature intra & intermolecular N—H···N hydrogen bonds (See hydrogen-bond geometry table and Fig 2).