The molecule of the title compound, C13H11N3OS, is non-planar; the dihedral angles between the thiourea and pyridine planes and between the thiourea and benzene planes are 41.28 (8) and 27.47 (8)°, respectively.
Supporting information
CCDC reference: 609353
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.043
- wR factor = 0.106
- Data-to-parameter ratio = 13.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96
PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - C6 .. 5.16 su
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
2 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
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
N-Benzoyl-
N'-(3-pyridyl)thiourea
top
Crystal data top
C13H11N3OS | Z = 2 |
Mr = 257.31 | F(000) = 268 |
Triclinic, P1 | Dx = 1.363 Mg m−3 |
Hall symbol: -P 1 | Melting point = 431–432 K |
a = 7.828 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.688 (2) Å | Cell parameters from 1073 reflections |
c = 10.892 (3) Å | θ = 2.7–25.9° |
α = 111.785 (3)° | µ = 0.25 mm−1 |
β = 92.152 (4)° | T = 293 K |
γ = 111.499 (4)° | Prism, colorless |
V = 627.0 (3) Å3 | 0.25 × 0.15 × 0.06 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2263 independent reflections |
Radiation source: fine-focus sealed tube | 1879 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.013 |
φ and ω scans | θmax = 25.5°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | h = −9→9 |
Tmin = 0.930, Tmax = 0.985 | k = −10→10 |
3239 measured reflections | l = −12→13 |
Refinement top
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0512P)2 + 0.1913P] where P = (Fo2 + 2Fc2)/3 |
2263 reflections | (Δ/σ)max < 0.001 |
163 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
Special details top
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 | x | y | z | Uiso*/Ueq | |
N1 | 0.2590 (3) | 0.6065 (2) | 0.55261 (18) | 0.0428 (4) | |
N2 | 0.2778 (2) | 0.1699 (2) | 0.48517 (17) | 0.0407 (4) | |
H2 | 0.2828 | 0.1400 | 0.4012 | 0.049* | |
N3 | 0.2196 (2) | −0.1298 (2) | 0.42742 (16) | 0.0366 (4) | |
H3A | 0.2030 | −0.2156 | 0.4533 | 0.044* | |
O1 | 0.2515 (2) | −0.06185 (19) | 0.24359 (14) | 0.0490 (4) | |
S1 | 0.21945 (9) | 0.05640 (7) | 0.68254 (5) | 0.0509 (2) | |
C1 | 0.2307 (3) | 0.4316 (3) | 0.4978 (2) | 0.0409 (5) | |
H1 | 0.1547 | 0.3583 | 0.4125 | 0.049* | |
C2 | 0.3083 (3) | 0.3530 (2) | 0.5608 (2) | 0.0359 (5) | |
C3 | 0.4218 (3) | 0.4607 (3) | 0.6869 (2) | 0.0441 (5) | |
H3 | 0.4779 | 0.4133 | 0.7316 | 0.053* | |
C4 | 0.4499 (3) | 0.6410 (3) | 0.7450 (2) | 0.0468 (5) | |
H4 | 0.5241 | 0.7168 | 0.8306 | 0.056* | |
C5 | 0.3676 (3) | 0.7080 (3) | 0.6756 (2) | 0.0432 (5) | |
H5 | 0.3887 | 0.8300 | 0.7163 | 0.052* | |
C6 | 0.2424 (3) | 0.0377 (2) | 0.52733 (19) | 0.0354 (5) | |
C7 | 0.2204 (3) | −0.1735 (3) | 0.2923 (2) | 0.0366 (5) | |
C8 | 0.1799 (3) | −0.3661 (3) | 0.20554 (19) | 0.0349 (4) | |
C9 | 0.2538 (3) | −0.4019 (3) | 0.0896 (2) | 0.0454 (5) | |
H9 | 0.3285 | −0.3062 | 0.0699 | 0.055* | |
C10 | 0.2177 (4) | −0.5779 (3) | 0.0031 (2) | 0.0551 (6) | |
H10 | 0.2704 | −0.6004 | −0.0733 | 0.066* | |
C11 | 0.1031 (4) | −0.7206 (3) | 0.0302 (2) | 0.0550 (6) | |
H11 | 0.0775 | −0.8395 | −0.0285 | 0.066* | |
C12 | 0.0267 (3) | −0.6870 (3) | 0.1439 (2) | 0.0521 (6) | |
H12 | −0.0511 | −0.7834 | 0.1617 | 0.062* | |
C13 | 0.0654 (3) | −0.5103 (3) | 0.2319 (2) | 0.0428 (5) | |
H13 | 0.0144 | −0.4882 | 0.3090 | 0.051* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0534 (11) | 0.0307 (9) | 0.0474 (11) | 0.0190 (8) | 0.0105 (9) | 0.0176 (8) |
N2 | 0.0616 (12) | 0.0305 (9) | 0.0333 (9) | 0.0221 (8) | 0.0140 (8) | 0.0132 (7) |
N3 | 0.0537 (11) | 0.0266 (8) | 0.0312 (9) | 0.0190 (8) | 0.0095 (8) | 0.0109 (7) |
O1 | 0.0738 (11) | 0.0353 (8) | 0.0368 (8) | 0.0197 (8) | 0.0124 (7) | 0.0162 (7) |
S1 | 0.0845 (5) | 0.0367 (3) | 0.0361 (3) | 0.0293 (3) | 0.0207 (3) | 0.0146 (2) |
C1 | 0.0513 (13) | 0.0317 (11) | 0.0372 (11) | 0.0155 (9) | 0.0071 (9) | 0.0136 (9) |
C2 | 0.0420 (11) | 0.0278 (10) | 0.0393 (11) | 0.0152 (9) | 0.0134 (9) | 0.0141 (9) |
C3 | 0.0481 (13) | 0.0381 (12) | 0.0466 (13) | 0.0197 (10) | 0.0048 (10) | 0.0166 (10) |
C4 | 0.0505 (13) | 0.0342 (11) | 0.0436 (12) | 0.0147 (10) | 0.0006 (10) | 0.0070 (9) |
C5 | 0.0476 (13) | 0.0269 (10) | 0.0521 (13) | 0.0147 (9) | 0.0111 (10) | 0.0136 (10) |
C6 | 0.0384 (11) | 0.0288 (10) | 0.0375 (11) | 0.0151 (9) | 0.0072 (9) | 0.0109 (9) |
C7 | 0.0410 (11) | 0.0329 (11) | 0.0366 (11) | 0.0164 (9) | 0.0083 (9) | 0.0135 (9) |
C8 | 0.0400 (11) | 0.0331 (10) | 0.0305 (10) | 0.0173 (9) | 0.0038 (8) | 0.0099 (8) |
C9 | 0.0567 (14) | 0.0402 (12) | 0.0363 (11) | 0.0184 (10) | 0.0118 (10) | 0.0139 (9) |
C10 | 0.0724 (17) | 0.0549 (15) | 0.0342 (12) | 0.0322 (13) | 0.0127 (11) | 0.0084 (11) |
C11 | 0.0806 (18) | 0.0368 (12) | 0.0397 (13) | 0.0293 (12) | 0.0035 (12) | 0.0032 (10) |
C12 | 0.0673 (16) | 0.0329 (12) | 0.0463 (13) | 0.0149 (11) | 0.0038 (12) | 0.0125 (10) |
C13 | 0.0532 (13) | 0.0372 (12) | 0.0350 (11) | 0.0169 (10) | 0.0103 (10) | 0.0132 (9) |
Geometric parameters (Å, º) top
N1—C5 | 1.335 (3) | C4—C5 | 1.374 (3) |
N1—C1 | 1.336 (3) | C4—H4 | 0.9300 |
N2—C6 | 1.332 (2) | C5—H5 | 0.9300 |
N2—C2 | 1.415 (2) | C7—C8 | 1.486 (3) |
N2—H2 | 0.8600 | C8—C13 | 1.385 (3) |
N3—C7 | 1.378 (2) | C8—C9 | 1.386 (3) |
N3—C6 | 1.398 (2) | C9—C10 | 1.378 (3) |
N3—H3A | 0.8600 | C9—H9 | 0.9300 |
O1—C7 | 1.224 (2) | C10—C11 | 1.380 (3) |
S1—C6 | 1.660 (2) | C10—H10 | 0.9300 |
C1—C2 | 1.387 (3) | C11—C12 | 1.376 (3) |
C1—H1 | 0.9300 | C11—H11 | 0.9300 |
C2—C3 | 1.377 (3) | C12—C13 | 1.383 (3) |
C3—C4 | 1.380 (3) | C12—H12 | 0.9300 |
C3—H3 | 0.9300 | C13—H13 | 0.9300 |
| | | |
C5—N1—C1 | 116.68 (18) | N2—C6—S1 | 125.80 (15) |
C6—N2—C2 | 128.35 (17) | N3—C6—S1 | 119.62 (14) |
C6—N2—H2 | 115.8 | O1—C7—N3 | 122.82 (18) |
C2—N2—H2 | 115.8 | O1—C7—C8 | 120.53 (18) |
C7—N3—C6 | 127.54 (16) | N3—C7—C8 | 116.65 (16) |
C7—N3—H3A | 116.2 | C13—C8—C9 | 118.98 (18) |
C6—N3—H3A | 116.2 | C13—C8—C7 | 123.14 (18) |
N1—C1—C2 | 123.8 (2) | C9—C8—C7 | 117.80 (18) |
N1—C1—H1 | 118.1 | C10—C9—C8 | 120.7 (2) |
C2—C1—H1 | 118.1 | C10—C9—H9 | 119.6 |
C3—C2—C1 | 118.53 (18) | C8—C9—H9 | 119.6 |
C3—C2—N2 | 124.16 (18) | C11—C10—C9 | 119.8 (2) |
C1—C2—N2 | 117.07 (18) | C11—C10—H10 | 120.1 |
C2—C3—C4 | 118.04 (19) | C9—C10—H10 | 120.1 |
C2—C3—H3 | 121.0 | C12—C11—C10 | 120.1 (2) |
C4—C3—H3 | 121.0 | C12—C11—H11 | 120.0 |
C5—C4—C3 | 119.7 (2) | C10—C11—H11 | 120.0 |
C5—C4—H4 | 120.2 | C11—C12—C13 | 120.1 (2) |
C3—C4—H4 | 120.2 | C11—C12—H12 | 119.9 |
N1—C5—C4 | 123.22 (19) | C13—C12—H12 | 119.9 |
N1—C5—H5 | 118.4 | C8—C13—C12 | 120.3 (2) |
C4—C5—H5 | 118.4 | C8—C13—H13 | 119.9 |
N2—C6—N3 | 114.56 (17) | C12—C13—H13 | 119.9 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1 | 0.86 | 1.87 | 2.597 (2) | 141 |
N3—H3A···N1i | 0.86 | 2.34 | 3.164 (3) | 162 |
Symmetry code: (i) x, y−1, z. |