organic compounds
In the title compound, C10H12N2OS, the ethyl and benzoyl groups are both cis with respect to the S atom across the thiourea C—N bonds, in contrast with the cis–trans arrangement seen in the arylbenzoylthiourea analogues. The crystal packing is stabilized by weak intermolecular N—HO hydrogen bonds, which form a one-dimensional polymeric chain along the a axis.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804005355/cv6279sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804005355/cv6279Isup2.hkl |
CCDC reference: 238783
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.006 Å
- R factor = 0.064
- wR factor = 0.159
- Data-to-parameter ratio = 17.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for N2 - C8 .. 6.54 su PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT416_ALERT_2_C Short Intra D-H..H-D H1A .. H2A .. 1.93 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C10 H12 N2 O S
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.90 From the CIF: _reflns_number_total 2171 Count of symmetry unique reflns 1226 Completeness (_total/calc) 177.08% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 945 Fraction of Friedel pairs measured 0.771 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 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 2 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 3 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); 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, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
N-Benzoyl-N'-ethylthiourea top
Crystal data top
C10H12N2OS | Dx = 1.282 Mg m−3 |
Mr = 208.28 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 1268 reflections |
a = 10.041 (5) Å | θ = 2.8–26.9° |
b = 9.389 (5) Å | µ = 0.27 mm−1 |
c = 11.450 (6) Å | T = 273 K |
V = 1079.5 (9) Å3 | Needle, colourless |
Z = 4 | 0.45 × 0.24 × 0.05 mm |
F(000) = 440 |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 1789 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.023 |
Graphite monochromator | θmax = 26.9°, θmin = 2.8° |
Detector resolution: 83.66 pixels mm-1 | h = −10→12 |
ω scans | k = −11→6 |
4704 measured reflections | l = −14→14 |
2171 independent reflections |
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)] = 0.064 | H-atom parameters constrained |
wR(F2) = 0.159 | w = 1/[σ2(Fo2) + (0.0691P)2 + 0.4025P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.001 |
2171 reflections | Δρmax = 0.35 e Å−3 |
127 parameters | Δρmin = −0.20 e Å−3 |
1 restraint | Absolute structure: Flack (1983), with how many Friedel pairs? |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.14 (18) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.60970 (11) | 0.00202 (16) | 0.59582 (16) | 0.0871 (5) | |
O1 | 0.6873 (2) | −0.2318 (3) | 0.7625 (3) | 0.0639 (8) | |
N1 | 0.4707 (3) | −0.2008 (3) | 0.7089 (3) | 0.0511 (8) | |
H1A | 0.3919 | −0.2320 | 0.7234 | 0.061* | |
N2 | 0.3558 (3) | −0.0417 (3) | 0.6158 (3) | 0.0570 (9) | |
H2A | 0.2894 | −0.0877 | 0.6444 | 0.068* | |
C1 | 0.6300 (4) | −0.4938 (5) | 0.8702 (5) | 0.0620 (11) | |
H1B | 0.7051 | −0.4460 | 0.8971 | 0.074* | |
C2 | 0.6068 (5) | −0.6314 (6) | 0.9045 (5) | 0.0769 (15) | |
H2B | 0.6665 | −0.6766 | 0.9544 | 0.092* | |
C3 | 0.4956 (6) | −0.7032 (5) | 0.8656 (5) | 0.0822 (15) | |
H3A | 0.4805 | −0.7967 | 0.8891 | 0.099* | |
C4 | 0.4071 (4) | −0.6364 (5) | 0.7921 (5) | 0.0708 (13) | |
H4A | 0.3325 | −0.6851 | 0.7653 | 0.085* | |
C5 | 0.4287 (4) | −0.4981 (4) | 0.7582 (4) | 0.0578 (10) | |
H5A | 0.3673 | −0.4527 | 0.7101 | 0.069* | |
C6 | 0.5416 (3) | −0.4252 (4) | 0.7953 (4) | 0.0505 (9) | |
C7 | 0.5757 (3) | −0.2798 (4) | 0.7562 (4) | 0.0500 (9) | |
C8 | 0.4778 (3) | −0.0801 (4) | 0.6424 (4) | 0.0518 (9) | |
C9 | 0.3326 (5) | 0.0777 (6) | 0.5387 (6) | 0.0837 (15) | |
H9A | 0.3559 | 0.0525 | 0.4591 | 0.100* | |
H9B | 0.3864 | 0.1585 | 0.5623 | 0.100* | |
C10 | 0.1885 (5) | 0.1139 (5) | 0.5464 (5) | 0.0802 (14) | |
H10A | 0.1696 | 0.1932 | 0.4961 | 0.120* | |
H10B | 0.1667 | 0.1387 | 0.6255 | 0.120* | |
H10C | 0.1363 | 0.0333 | 0.5227 | 0.120* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0551 (6) | 0.0894 (8) | 0.1167 (11) | −0.0195 (6) | 0.0091 (8) | 0.0346 (8) |
O1 | 0.0320 (11) | 0.0659 (17) | 0.094 (2) | −0.0027 (11) | −0.0059 (13) | −0.0016 (16) |
N1 | 0.0300 (13) | 0.0531 (17) | 0.070 (2) | −0.0023 (12) | 0.0022 (13) | 0.0106 (16) |
N2 | 0.0292 (12) | 0.0571 (17) | 0.085 (2) | 0.0023 (12) | 0.0067 (16) | 0.0357 (18) |
C1 | 0.050 (2) | 0.071 (3) | 0.065 (3) | 0.007 (2) | −0.0084 (18) | 0.005 (2) |
C2 | 0.071 (3) | 0.078 (3) | 0.081 (3) | 0.018 (2) | 0.000 (3) | 0.020 (3) |
C3 | 0.086 (3) | 0.059 (3) | 0.102 (4) | 0.008 (3) | 0.011 (3) | 0.021 (3) |
C4 | 0.062 (2) | 0.060 (3) | 0.091 (4) | −0.009 (2) | −0.004 (3) | 0.005 (3) |
C5 | 0.0454 (19) | 0.057 (2) | 0.071 (3) | 0.0021 (15) | −0.002 (2) | 0.001 (2) |
C6 | 0.0360 (16) | 0.055 (2) | 0.060 (2) | 0.0050 (15) | 0.0048 (16) | 0.0005 (19) |
C7 | 0.0315 (14) | 0.056 (2) | 0.062 (2) | 0.0035 (14) | 0.0013 (16) | −0.0080 (19) |
C8 | 0.0453 (19) | 0.054 (2) | 0.056 (2) | −0.0027 (15) | 0.0020 (17) | 0.0024 (18) |
C9 | 0.066 (3) | 0.084 (3) | 0.102 (4) | 0.004 (2) | 0.002 (3) | 0.043 (3) |
C10 | 0.084 (3) | 0.070 (3) | 0.087 (3) | 0.016 (2) | −0.016 (3) | 0.012 (3) |
Geometric parameters (Å, º) top
S1—C8 | 1.623 (4) | C3—C4 | 1.375 (7) |
O1—C7 | 1.209 (4) | C3—H3A | 0.9300 |
N1—C8 | 1.367 (5) | C4—C5 | 1.373 (6) |
N1—C7 | 1.399 (4) | C4—H4A | 0.9300 |
N1—H1A | 0.8600 | C5—C6 | 1.391 (5) |
N2—C8 | 1.312 (4) | C5—H5A | 0.9300 |
N2—C9 | 1.446 (6) | C6—C7 | 1.477 (6) |
N2—H2A | 0.8600 | C9—C10 | 1.489 (7) |
C1—C2 | 1.371 (6) | C9—H9A | 0.9700 |
C1—C6 | 1.392 (6) | C9—H9B | 0.9700 |
C1—H1B | 0.9300 | C10—H10A | 0.9600 |
C2—C3 | 1.378 (7) | C10—H10B | 0.9600 |
C2—H2B | 0.9300 | C10—H10C | 0.9600 |
C8—N1—C7 | 128.0 (3) | C5—C6—C1 | 118.7 (4) |
C8—N1—H1A | 116.0 | C5—C6—C7 | 123.5 (4) |
C7—N1—H1A | 116.0 | C1—C6—C7 | 117.8 (3) |
C8—N2—C9 | 120.4 (3) | O1—C7—N1 | 121.6 (4) |
C8—N2—H2A | 119.8 | O1—C7—C6 | 122.8 (3) |
C9—N2—H2A | 119.8 | N1—C7—C6 | 115.6 (3) |
C2—C1—C6 | 120.3 (4) | N2—C8—N1 | 108.0 (3) |
C2—C1—H1B | 119.9 | N2—C8—S1 | 123.7 (3) |
C6—C1—H1B | 119.9 | N1—C8—S1 | 128.3 (3) |
C1—C2—C3 | 120.4 (5) | N2—C9—C10 | 107.3 (4) |
C1—C2—H2B | 119.8 | N2—C9—H9A | 110.3 |
C3—C2—H2B | 119.8 | C10—C9—H9A | 110.2 |
C4—C3—C2 | 119.9 (4) | N2—C9—H9B | 110.2 |
C4—C3—H3A | 120.1 | C10—C9—H9B | 110.3 |
C2—C3—H3A | 120.1 | H9A—C9—H9B | 108.5 |
C5—C4—C3 | 120.2 (5) | C9—C10—H10A | 109.5 |
C5—C4—H4A | 119.9 | C9—C10—H10B | 109.5 |
C3—C4—H4A | 119.9 | H10A—C10—H10B | 109.5 |
C4—C5—C6 | 120.5 (4) | C9—C10—H10C | 109.5 |
C4—C5—H5A | 119.8 | H10A—C10—H10C | 109.5 |
C6—C5—H5A | 119.8 | H10B—C10—H10C | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.86 | 2.13 | 2.979 (4) | 169 |
N2—H2A···O1i | 0.86 | 2.40 | 3.195 (4) | 154 |
C5—H5A···O1i | 0.93 | 2.57 | 3.246 (5) | 129 |
Symmetry code: (i) x−1/2, −y−1/2, z. |