In the title compound, C
10H
11N
3OS, the pyridine ring makes a dihedral angle of 86.8 (3)° with the cyclopropane ring. The amide group and the pyridine are linked by an intermolecular N—H
N hydrogen bond.
Supporting information
CCDC reference: 624510
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.038
- wR factor = 0.108
- Data-to-parameter ratio = 14.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C10
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 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
0 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
1-Cyclopropylcarbonyl-3-(2-pyridyl)thiourea
top
Crystal data top
C10H11N3OS | Dx = 1.307 Mg m−3 |
Mr = 221.28 | Melting point: 417 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.457 (3) Å | Cell parameters from 1637 reflections |
b = 12.178 (4) Å | θ = 2.4–23.7° |
c = 10.998 (4) Å | µ = 0.27 mm−1 |
β = 96.958 (4)° | T = 293 K |
V = 1124.4 (7) Å3 | Block, colorless |
Z = 4 | 0.34 × 0.32 × 0.21 mm |
F(000) = 464 | |
Data collection top
Bruker APEX-II CCD area-detector diffractometer | 1984 independent reflections |
Radiation source: fine-focus sealed tube | 1390 reflections with I > σ(I) |
Graphite monochromator | Rint = 0.055 |
φ and ω scans | θmax = 25.0°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −10→9 |
Tmin = 0.970, Tmax = 0.983 | k = −11→14 |
5822 measured reflections | l = −11→13 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.108 | w = 1/[σ2(Fo2) + (0.0471P)2 + 0.2411P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
1984 reflections | Δρmax = 0.28 e Å−3 |
136 parameters | Δρmin = −0.32 e Å−3 |
0 restraints | Extinction correction: SHELXL97 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0045 (6) |
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 | |
S1 | 0.73747 (7) | 0.79536 (5) | 0.17582 (6) | 0.0680 (3) | |
O1 | 1.15528 (18) | 0.69558 (11) | −0.02610 (13) | 0.0558 (4) | |
N1 | 0.9038 (2) | 0.94942 (13) | −0.17013 (14) | 0.0473 (4) | |
N2 | 0.91308 (18) | 0.83131 (13) | −0.00995 (14) | 0.0443 (4) | |
H2' | 0.9900 | 0.8049 | −0.0453 | 0.053* | |
N3 | 0.99023 (19) | 0.69124 (12) | 0.12425 (15) | 0.0442 (4) | |
H3' | 0.9733 | 0.6555 | 0.1889 | 0.053* | |
C1 | 0.8416 (2) | 0.92542 (15) | −0.06719 (17) | 0.0407 (5) | |
C2 | 0.8480 (3) | 1.03883 (17) | −0.23238 (19) | 0.0557 (6) | |
H2 | 0.8906 | 1.0564 | −0.3040 | 0.067* | |
C3 | 0.7325 (3) | 1.10553 (18) | −0.1967 (2) | 0.0586 (6) | |
H3 | 0.6958 | 1.1660 | −0.2435 | 0.070* | |
C4 | 0.6719 (3) | 1.08077 (17) | −0.0895 (2) | 0.0606 (6) | |
H4 | 0.5943 | 1.1254 | −0.0621 | 0.073* | |
C5 | 0.7265 (2) | 0.98940 (17) | −0.0226 (2) | 0.0536 (6) | |
H5 | 0.6871 | 0.9715 | 0.0502 | 0.064* | |
C6 | 0.8828 (2) | 0.77534 (15) | 0.09005 (18) | 0.0419 (5) | |
C7 | 1.1202 (2) | 0.65673 (16) | 0.06958 (18) | 0.0457 (5) | |
C8 | 1.2137 (3) | 0.56989 (18) | 0.1382 (2) | 0.0579 (6) | |
H8 | 1.1707 | 0.5406 | 0.2105 | 0.070* | |
C9 | 1.3077 (3) | 0.4919 (2) | 0.0697 (3) | 0.0792 (8) | |
H9A | 1.3179 | 0.4167 | 0.0986 | 0.095* | |
H9B | 1.3005 | 0.5001 | −0.0186 | 0.095* | |
C10 | 1.3913 (3) | 0.5759 (3) | 0.1445 (3) | 0.0870 (9) | |
H10A | 1.4362 | 0.6365 | 0.1030 | 0.104* | |
H10B | 1.4536 | 0.5531 | 0.2202 | 0.104* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0657 (4) | 0.0725 (5) | 0.0719 (5) | 0.0199 (3) | 0.0334 (3) | 0.0212 (3) |
O1 | 0.0671 (10) | 0.0556 (9) | 0.0483 (9) | 0.0139 (7) | 0.0217 (7) | 0.0061 (7) |
N1 | 0.0617 (11) | 0.0414 (10) | 0.0387 (10) | −0.0004 (8) | 0.0061 (8) | 0.0013 (8) |
N2 | 0.0499 (10) | 0.0433 (9) | 0.0417 (9) | 0.0085 (8) | 0.0135 (7) | 0.0031 (7) |
N3 | 0.0512 (10) | 0.0417 (10) | 0.0415 (10) | 0.0066 (8) | 0.0137 (7) | 0.0060 (7) |
C1 | 0.0447 (11) | 0.0357 (11) | 0.0407 (11) | −0.0005 (9) | 0.0017 (9) | −0.0007 (8) |
C2 | 0.0737 (16) | 0.0465 (13) | 0.0455 (13) | −0.0036 (12) | 0.0012 (11) | 0.0048 (10) |
C3 | 0.0650 (15) | 0.0431 (12) | 0.0642 (15) | 0.0020 (11) | −0.0071 (12) | 0.0097 (11) |
C4 | 0.0507 (13) | 0.0468 (13) | 0.0837 (18) | 0.0088 (10) | 0.0062 (12) | 0.0020 (12) |
C5 | 0.0530 (13) | 0.0469 (13) | 0.0624 (14) | 0.0062 (10) | 0.0130 (10) | 0.0036 (10) |
C6 | 0.0452 (11) | 0.0375 (11) | 0.0435 (11) | 0.0004 (9) | 0.0068 (9) | −0.0015 (9) |
C7 | 0.0534 (12) | 0.0410 (11) | 0.0432 (12) | 0.0049 (9) | 0.0083 (9) | −0.0031 (9) |
C8 | 0.0639 (15) | 0.0585 (14) | 0.0541 (14) | 0.0210 (11) | 0.0181 (11) | 0.0133 (11) |
C9 | 0.099 (2) | 0.0681 (17) | 0.0730 (18) | 0.0394 (16) | 0.0210 (15) | 0.0095 (14) |
C10 | 0.0634 (17) | 0.099 (2) | 0.097 (2) | 0.0236 (15) | 0.0036 (15) | 0.0191 (18) |
Geometric parameters (Å, º) top
S1—C6 | 1.655 (2) | C3—H3 | 0.9300 |
O1—C7 | 1.223 (2) | C4—C5 | 1.383 (3) |
N1—C1 | 1.337 (2) | C4—H4 | 0.9300 |
N1—C2 | 1.341 (3) | C5—H5 | 0.9300 |
N2—C6 | 1.345 (2) | C7—C8 | 1.473 (3) |
N2—C1 | 1.408 (2) | C8—C10 | 1.497 (3) |
N2—H2' | 0.8600 | C8—C9 | 1.500 (3) |
N3—C7 | 1.381 (2) | C8—H8 | 0.9800 |
N3—C6 | 1.391 (2) | C9—C10 | 1.443 (4) |
N3—H3' | 0.8600 | C9—H9A | 0.9700 |
C1—C5 | 1.382 (3) | C9—H9B | 0.9700 |
C2—C3 | 1.365 (3) | C10—H10A | 0.9700 |
C2—H2 | 0.9300 | C10—H10B | 0.9700 |
C3—C4 | 1.374 (3) | | |
| | | |
C1—N1—C2 | 117.38 (18) | N2—C6—S1 | 128.29 (15) |
C6—N2—C1 | 131.61 (17) | N3—C6—S1 | 117.41 (14) |
C6—N2—H2' | 114.2 | O1—C7—N3 | 123.10 (18) |
C1—N2—H2' | 114.2 | O1—C7—C8 | 123.22 (19) |
C7—N3—C6 | 129.42 (17) | N3—C7—C8 | 113.67 (18) |
C7—N3—H3' | 115.3 | C7—C8—C10 | 117.5 (2) |
C6—N3—H3' | 115.3 | C7—C8—C9 | 118.8 (2) |
N1—C1—C5 | 122.90 (18) | C10—C8—C9 | 57.58 (16) |
N1—C1—N2 | 111.39 (16) | C7—C8—H8 | 116.6 |
C5—C1—N2 | 125.65 (18) | C10—C8—H8 | 116.6 |
N1—C2—C3 | 123.8 (2) | C9—C8—H8 | 116.6 |
N1—C2—H2 | 118.1 | C10—C9—C8 | 61.10 (17) |
C3—C2—H2 | 118.1 | C10—C9—H9A | 117.7 |
C2—C3—C4 | 118.1 (2) | C8—C9—H9A | 117.7 |
C2—C3—H3 | 121.0 | C10—C9—H9B | 117.7 |
C4—C3—H3 | 121.0 | C8—C9—H9B | 117.7 |
C3—C4—C5 | 119.9 (2) | H9A—C9—H9B | 114.8 |
C3—C4—H4 | 120.1 | C9—C10—C8 | 61.32 (17) |
C5—C4—H4 | 120.1 | C9—C10—H10A | 117.6 |
C1—C5—C4 | 118.0 (2) | C8—C10—H10A | 117.6 |
C1—C5—H5 | 121.0 | C9—C10—H10B | 117.6 |
C4—C5—H5 | 121.0 | C8—C10—H10B | 117.6 |
N2—C6—N3 | 114.30 (17) | H10A—C10—H10B | 114.7 |
| | | |
C2—N1—C1—C5 | −1.2 (3) | C1—N2—C6—S1 | 4.8 (3) |
C2—N1—C1—N2 | −178.70 (16) | C7—N3—C6—N2 | −1.1 (3) |
C6—N2—C1—N1 | −176.12 (19) | C7—N3—C6—S1 | 179.60 (16) |
C6—N2—C1—C5 | 6.5 (3) | C6—N3—C7—O1 | −3.7 (3) |
C1—N1—C2—C3 | −0.1 (3) | C6—N3—C7—C8 | 175.50 (19) |
N1—C2—C3—C4 | 1.3 (3) | O1—C7—C8—C10 | 38.7 (3) |
C2—C3—C4—C5 | −1.1 (3) | N3—C7—C8—C10 | −140.5 (2) |
N1—C1—C5—C4 | 1.4 (3) | O1—C7—C8—C9 | −27.5 (3) |
N2—C1—C5—C4 | 178.49 (18) | N3—C7—C8—C9 | 153.3 (2) |
C3—C4—C5—C1 | −0.2 (3) | C7—C8—C9—C10 | 106.0 (3) |
C1—N2—C6—N3 | −174.46 (17) | C7—C8—C10—C9 | −108.2 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2′···O1 | 0.86 | 1.92 | 2.655 (2) | 142 |
N3—H3′···N1i | 0.86 | 2.15 | 2.997 (2) | 171 |
Symmetry code: (i) x, −y+3/2, z+1/2. |