In the title compound, C7H8N2S, the C-N(imino) and C-N(amino) bond distances within the thiourea moiety are 1.3395 (18) and 1.321 (2) Å, respectively. This significant difference in magnitude is also observed for some halogen-phenylthiourea compounds.
Supporting information
CCDC reference: 245298
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.037
- wR factor = 0.091
- Data-to-parameter ratio = 17.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for S - C1 .. 5.20 su
PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2A ... ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6 .. S .. 2.94 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Crystal data top
C7H8N2S | F(000) = 320 |
Mr = 152.21 | Dx = 1.331 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5560 reflections |
a = 5.6991 (4) Å | θ = 2.7–27.0° |
b = 15.2962 (10) Å | µ = 0.35 mm−1 |
c = 8.7352 (8) Å | T = 295 K |
β = 93.7430 (16)° | Prism, yellow |
V = 759.86 (10) Å3 | 0.26 × 0.24 × 0.22 mm |
Z = 4 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 1428 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.022 |
Graphite monochromator | θmax = 27.5°, θmin = 2.7° |
Detector resolution: 10.00 pixels mm-1 | h = −7→7 |
ω scans | k = −19→19 |
6947 measured reflections | l = −10→11 |
1734 independent reflections | |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0425P)2 + 0.1385P] where P = (Fo2 + 2Fc2)/3 |
1734 reflections | (Δ/σ)max = 0.001 |
100 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.24 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 | |
S | 1.08439 (8) | 0.52051 (3) | 0.25354 (4) | 0.06057 (17) | |
N1 | 0.7880 (3) | 0.41116 (9) | 0.10789 (14) | 0.0520 (3) | |
N2 | 0.7622 (3) | 0.42076 (12) | 0.36669 (15) | 0.0661 (5) | |
C1 | 0.8645 (3) | 0.44607 (11) | 0.24269 (15) | 0.0469 (3) | |
C2 | 0.6185 (3) | 0.34289 (9) | 0.08511 (15) | 0.0434 (3) | |
C3 | 0.4158 (3) | 0.35823 (11) | −0.00365 (19) | 0.0573 (4) | |
H3 | 0.3864 | 0.4135 | −0.0450 | 0.069* | |
C4 | 0.2551 (3) | 0.29180 (13) | −0.0317 (2) | 0.0702 (5) | |
H4 | 0.1188 | 0.3021 | −0.0934 | 0.084* | |
C5 | 0.2955 (3) | 0.21060 (12) | 0.0309 (2) | 0.0665 (5) | |
H5 | 0.1859 | 0.1661 | 0.0129 | 0.080* | |
C6 | 0.4974 (4) | 0.19525 (12) | 0.1199 (2) | 0.0650 (5) | |
H6 | 0.5244 | 0.1402 | 0.1628 | 0.078* | |
C7 | 0.6621 (3) | 0.26092 (11) | 0.1467 (2) | 0.0573 (4) | |
H7 | 0.8008 | 0.2499 | 0.2057 | 0.069* | |
H1 | 0.844 (3) | 0.4322 (12) | 0.031 (2) | 0.060* | |
H2B | 0.809 (3) | 0.4441 (12) | 0.450 (2) | 0.060* | |
H2A | 0.648 (3) | 0.3872 (12) | 0.358 (2) | 0.060* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S | 0.0736 (3) | 0.0726 (3) | 0.0349 (2) | −0.0282 (2) | −0.00084 (18) | −0.00292 (17) |
N1 | 0.0621 (8) | 0.0642 (8) | 0.0298 (6) | −0.0198 (7) | 0.0033 (5) | −0.0001 (5) |
N2 | 0.0722 (10) | 0.0940 (12) | 0.0322 (6) | −0.0324 (9) | 0.0056 (6) | −0.0069 (7) |
C1 | 0.0521 (8) | 0.0556 (8) | 0.0325 (6) | −0.0045 (7) | −0.0017 (6) | 0.0004 (6) |
C2 | 0.0487 (8) | 0.0494 (8) | 0.0326 (6) | −0.0047 (6) | 0.0061 (6) | −0.0027 (6) |
C3 | 0.0613 (10) | 0.0520 (9) | 0.0571 (9) | 0.0012 (8) | −0.0086 (8) | 0.0001 (7) |
C4 | 0.0526 (10) | 0.0793 (13) | 0.0765 (12) | −0.0071 (9) | −0.0118 (9) | −0.0098 (10) |
C5 | 0.0644 (11) | 0.0619 (11) | 0.0750 (12) | −0.0190 (9) | 0.0173 (9) | −0.0154 (9) |
C6 | 0.0805 (12) | 0.0480 (9) | 0.0685 (11) | −0.0025 (8) | 0.0191 (10) | 0.0029 (8) |
C7 | 0.0542 (9) | 0.0621 (10) | 0.0554 (10) | 0.0044 (8) | 0.0009 (7) | 0.0084 (8) |
Geometric parameters (Å, º) top
S—C1 | 1.6915 (16) | C3—C4 | 1.379 (2) |
N1—C1 | 1.3395 (18) | C3—H3 | 0.9300 |
N1—C2 | 1.4276 (19) | C4—C5 | 1.371 (3) |
N1—H1 | 0.827 (19) | C4—H4 | 0.9300 |
N2—C1 | 1.321 (2) | C5—C6 | 1.366 (3) |
N2—H2B | 0.84 (2) | C5—H5 | 0.9300 |
N2—H2A | 0.83 (2) | C6—C7 | 1.384 (2) |
C2—C3 | 1.369 (2) | C6—H6 | 0.9300 |
C2—C7 | 1.381 (2) | C7—H7 | 0.9300 |
| | | |
C1—N1—C2 | 126.33 (13) | C4—C3—H3 | 120.0 |
C1—N1—H1 | 115.8 (13) | C5—C4—C3 | 120.30 (18) |
C2—N1—H1 | 117.8 (13) | C5—C4—H4 | 119.8 |
C1—N2—H2B | 116.8 (13) | C3—C4—H4 | 119.8 |
C1—N2—H2A | 119.5 (13) | C6—C5—C4 | 119.74 (17) |
H2B—N2—H2A | 123.5 (18) | C6—C5—H5 | 120.1 |
N2—C1—N1 | 117.93 (15) | C4—C5—H5 | 120.1 |
N2—C1—S | 121.08 (12) | C5—C6—C7 | 120.55 (17) |
N1—C1—S | 120.99 (11) | C5—C6—H6 | 119.7 |
C3—C2—C7 | 120.01 (15) | C7—C6—H6 | 119.7 |
C3—C2—N1 | 119.46 (14) | C2—C7—C6 | 119.36 (16) |
C7—C2—N1 | 120.48 (14) | C2—C7—H7 | 120.3 |
C2—C3—C4 | 120.02 (16) | C6—C7—H7 | 120.3 |
C2—C3—H3 | 120.0 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Si | 0.827 (18) | 2.646 (17) | 3.4480 (14) | 163.8 (16) |
N2—H2B···Sii | 0.838 (18) | 2.676 (17) | 3.4925 (14) | 164.9 (16) |
C6—H6···Siii | 0.93 | 2.94 | 3.702 (2) | 140 |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+2, −y+1, −z+1; (iii) −x+2, y−1/2, −z+1/2. |