Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038433/bi2219sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038433/bi2219Isup2.hkl |
CCDC reference: 660270
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.043
- wR factor = 0.128
- Data-to-parameter ratio = 15.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C11 H13 N3 O3 S
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 1 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 0 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 0 ALERT type 5 Informative message, check
To a stirring acetone solution (75 ml) of butyrylchloride (2.0 g, 19 mmol) and ammoniumthiocyanate (1.43 g, 19 mmol), 4-nitroaniline (2.59 g, 19 mmol) in 45 ml of acetone was added dropwise. The solution mixture was refluxed for 1 h. The resulting solution was poured into a beaker containing some ice blocks. The white precipitate was filtered off and washed with distilled water and cold ethanol then dried under vacuum. Good quality crystals were obtained by recrystallization from DMSO. Yield 74% (2.03 g).
All H atoms were visible in difference Fourier maps, but were placed geometrically at ideal positions then allowed to ride on their parent C or N atoms with C—H = 0.93–0.97 Å and N—H = 0.86 Å, and with Uiso(H)= 1.2(C/N) or 1.5Ueq(methyl C).
The title compound is similar to the previously reported compound N-(4-methylbenzoyl)-N'-(4-nitrophenyl)thiourea (Yusof et al., 2006), except that the 4-methylbenzoyl group is replaced by a butanoyl group. The bond lengths and angles are comparable to those in that compound and to other thiourea derivatives (Yusof et al., 2007a,b). The central thiourea fragment (S1/C5/N1/N2) and phenyl ring (C6–C7) are essentially planar with maximum deviation of 0.013 (1) Å for atom N1, and the dihedral angle between them is 5.27 (8)°. An intramolecular hydrogen bond, N2—H2A···O1, forms a pseudo-six-membered ring (O1···H2A/N2/C5/N1/C4), and a relatively short intramolecular C—H···S contact is also observed (H11A···S1 = 2.56 Å, C11···S1 = 3.222 (2) Å, C11—H11A···S1 = 128 °). In the crystal structure, the molecules are linked into two-dimensional networks parallel to the bc planes via intermolecular N—H···S and C—H···O interactions (Fig. 2 & Table 1).
For some related structures, see: Yusof et al. (2006, 2007a,b).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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, 1997); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
C11H13N3O3S | F(000) = 560 |
Mr = 267.30 | Dx = 1.367 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 894 reflections |
a = 4.9002 (12) Å | θ = 1.9–26° |
b = 12.385 (3) Å | µ = 0.25 mm−1 |
c = 21.774 (5) Å | T = 293 K |
β = 100.727 (6)° | Block, light yellow |
V = 1298.3 (5) Å3 | 0.51 × 0.50 × 0.46 mm |
Z = 4 |
Bruker SMART APEX CCD diffractometer | 2540 independent reflections |
Radiation source: fine-focus sealed tube | 1933 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
ω scans | θmax = 26.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −6→3 |
Tmin = 0.882, Tmax = 0.892 | k = −15→14 |
7048 measured reflections | l = −26→26 |
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) = 0.128 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0696P)2 + 0.2521P] where P = (Fo2 + 2Fc2)/3 |
2540 reflections | (Δ/σ)max < 0.001 |
164 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C11H13N3O3S | V = 1298.3 (5) Å3 |
Mr = 267.30 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 4.9002 (12) Å | µ = 0.25 mm−1 |
b = 12.385 (3) Å | T = 293 K |
c = 21.774 (5) Å | 0.51 × 0.50 × 0.46 mm |
β = 100.727 (6)° |
Bruker SMART APEX CCD diffractometer | 2540 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 1933 reflections with I > 2σ(I) |
Tmin = 0.882, Tmax = 0.892 | Rint = 0.018 |
7048 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.23 e Å−3 |
2540 reflections | Δρmin = −0.16 e Å−3 |
164 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 | ||
S1 | 0.82531 (12) | −0.85936 (4) | −0.46315 (2) | 0.0606 (2) | |
O1 | 0.5256 (3) | −1.15131 (11) | −0.36784 (8) | 0.0678 (4) | |
O2 | −0.0653 (4) | −0.61661 (16) | −0.22970 (9) | 0.0912 (6) | |
O3 | 0.1567 (5) | −0.50150 (15) | −0.27592 (10) | 0.1057 (7) | |
N1 | 0.7852 (3) | −1.06019 (12) | −0.42783 (7) | 0.0538 (4) | |
H1A | 0.9045 | −1.0698 | −0.4517 | 0.065* | |
N2 | 0.5553 (3) | −0.93999 (12) | −0.37607 (7) | 0.0535 (4) | |
H2A | 0.5099 | −0.9994 | −0.3602 | 0.064* | |
N3 | 0.0939 (4) | −0.59385 (17) | −0.26469 (9) | 0.0716 (5) | |
C1 | 0.8042 (7) | −1.4546 (2) | −0.43218 (16) | 0.1014 (10) | |
H1B | 0.6911 | −1.5166 | −0.4282 | 0.152* | |
H1C | 0.9840 | −1.4639 | −0.4063 | 0.152* | |
H1D | 0.8242 | −1.4469 | −0.4750 | 0.152* | |
C2 | 0.6687 (6) | −1.35530 (18) | −0.41193 (14) | 0.0844 (8) | |
H2B | 0.4791 | −1.3512 | −0.4347 | 0.101* | |
H2C | 0.6622 | −1.3613 | −0.3678 | 0.101* | |
C3 | 0.8166 (5) | −1.25460 (17) | −0.42254 (12) | 0.0687 (6) | |
H3A | 0.8229 | −1.2495 | −0.4667 | 0.082* | |
H3B | 1.0066 | −1.2599 | −0.4001 | 0.082* | |
C4 | 0.6927 (4) | −1.15281 (16) | −0.40304 (10) | 0.0557 (5) | |
C5 | 0.7122 (4) | −0.95391 (15) | −0.41966 (8) | 0.0478 (4) | |
C6 | 0.4504 (4) | −0.84770 (14) | −0.35126 (9) | 0.0482 (4) | |
C7 | 0.2850 (4) | −0.86884 (16) | −0.30707 (9) | 0.0558 (5) | |
H7A | 0.2536 | −0.9400 | −0.2966 | 0.067* | |
C8 | 0.1682 (4) | −0.78694 (17) | −0.27893 (9) | 0.0598 (5) | |
H8A | 0.0564 | −0.8015 | −0.2498 | 0.072* | |
C9 | 0.2196 (4) | −0.68234 (17) | −0.29470 (9) | 0.0567 (5) | |
C10 | 0.3827 (5) | −0.65870 (16) | −0.33746 (11) | 0.0635 (6) | |
H10A | 0.4146 | −0.5873 | −0.3472 | 0.076* | |
C11 | 0.4999 (4) | −0.74187 (16) | −0.36612 (10) | 0.0611 (5) | |
H11A | 0.6114 | −0.7267 | −0.3952 | 0.073* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0715 (4) | 0.0573 (3) | 0.0613 (4) | 0.0000 (2) | 0.0338 (3) | 0.0062 (2) |
O1 | 0.0797 (11) | 0.0556 (8) | 0.0808 (10) | −0.0014 (7) | 0.0480 (9) | 0.0016 (7) |
O2 | 0.0923 (13) | 0.0943 (13) | 0.0985 (13) | 0.0146 (10) | 0.0478 (11) | −0.0184 (10) |
O3 | 0.1409 (18) | 0.0634 (12) | 0.1246 (16) | 0.0070 (11) | 0.0552 (14) | −0.0201 (10) |
N1 | 0.0552 (10) | 0.0537 (9) | 0.0599 (10) | −0.0003 (7) | 0.0298 (8) | −0.0014 (7) |
N2 | 0.0584 (10) | 0.0490 (9) | 0.0599 (9) | −0.0002 (7) | 0.0285 (8) | 0.0028 (7) |
N3 | 0.0749 (13) | 0.0690 (13) | 0.0720 (12) | 0.0105 (10) | 0.0166 (10) | −0.0164 (10) |
C1 | 0.127 (3) | 0.0594 (15) | 0.131 (2) | 0.0039 (15) | 0.058 (2) | −0.0052 (15) |
C2 | 0.105 (2) | 0.0579 (14) | 0.105 (2) | −0.0031 (12) | 0.0562 (17) | −0.0037 (12) |
C3 | 0.0747 (15) | 0.0552 (12) | 0.0860 (16) | 0.0019 (10) | 0.0399 (12) | 0.0003 (10) |
C4 | 0.0574 (12) | 0.0538 (11) | 0.0607 (12) | −0.0012 (9) | 0.0236 (10) | −0.0002 (8) |
C5 | 0.0432 (10) | 0.0551 (11) | 0.0473 (10) | −0.0004 (8) | 0.0143 (8) | 0.0000 (8) |
C6 | 0.0458 (10) | 0.0505 (10) | 0.0510 (10) | 0.0013 (8) | 0.0161 (8) | −0.0015 (8) |
C7 | 0.0615 (13) | 0.0548 (11) | 0.0571 (11) | 0.0016 (9) | 0.0267 (10) | 0.0043 (9) |
C8 | 0.0606 (12) | 0.0674 (13) | 0.0564 (11) | 0.0036 (10) | 0.0241 (10) | −0.0014 (9) |
C9 | 0.0532 (12) | 0.0616 (12) | 0.0567 (11) | 0.0073 (9) | 0.0140 (9) | −0.0097 (9) |
C10 | 0.0697 (14) | 0.0464 (11) | 0.0781 (15) | −0.0015 (9) | 0.0231 (12) | −0.0017 (9) |
C11 | 0.0659 (13) | 0.0543 (11) | 0.0716 (13) | −0.0034 (9) | 0.0346 (11) | −0.0003 (10) |
S1—C5 | 1.6646 (19) | C2—H2B | 0.970 |
O1—C4 | 1.221 (2) | C2—H2C | 0.970 |
O2—N3 | 1.221 (3) | C3—C4 | 1.495 (3) |
O3—N3 | 1.221 (3) | C3—H3A | 0.970 |
N1—C4 | 1.380 (2) | C3—H3B | 0.970 |
N1—C5 | 1.384 (2) | C6—C11 | 1.382 (3) |
N1—H1A | 0.860 | C6—C7 | 1.393 (3) |
N2—C5 | 1.339 (2) | C7—C8 | 1.365 (3) |
N2—C6 | 1.402 (2) | C7—H7A | 0.930 |
N2—H2A | 0.860 | C8—C9 | 1.375 (3) |
N3—C9 | 1.469 (3) | C8—H8A | 0.930 |
C1—C2 | 1.503 (3) | C9—C10 | 1.367 (3) |
C1—H1B | 0.960 | C10—C11 | 1.383 (3) |
C1—H1C | 0.960 | C10—H10A | 0.930 |
C1—H1D | 0.960 | C11—H11A | 0.930 |
C2—C3 | 1.482 (3) | ||
C4—N1—C5 | 128.95 (16) | H3A—C3—H3B | 107.5 |
C4—N1—H1A | 115.6 | O1—C4—N1 | 122.71 (17) |
C5—N1—H1A | 115.5 | O1—C4—C3 | 123.12 (17) |
C5—N2—C6 | 132.70 (16) | N1—C4—C3 | 114.17 (17) |
C5—N2—H2A | 113.6 | N2—C5—N1 | 114.19 (16) |
C6—N2—H2A | 113.7 | N2—C5—S1 | 127.48 (14) |
O2—N3—O3 | 123.7 (2) | N1—C5—S1 | 118.32 (13) |
O2—N3—C9 | 118.4 (2) | C11—C6—C7 | 119.32 (17) |
O3—N3—C9 | 117.9 (2) | C11—C6—N2 | 126.15 (17) |
C2—C1—H1B | 109.5 | C7—C6—N2 | 114.52 (16) |
C2—C1—H1C | 109.5 | C8—C7—C6 | 121.12 (18) |
H1B—C1—H1C | 109.5 | C8—C7—H7A | 119.4 |
C2—C1—H1D | 109.5 | C6—C7—H7A | 119.4 |
H1B—C1—H1D | 109.5 | C7—C8—C9 | 118.45 (19) |
H1C—C1—H1D | 109.5 | C7—C8—H8A | 120.8 |
C3—C2—C1 | 112.8 (2) | C9—C8—H8A | 120.8 |
C3—C2—H2B | 109.0 | C10—C9—C8 | 121.95 (18) |
C1—C2—H2B | 109.0 | C10—C9—N3 | 119.3 (2) |
C3—C2—H2C | 109.0 | C8—C9—N3 | 118.7 (2) |
C1—C2—H2C | 109.0 | C9—C10—C11 | 119.49 (19) |
H2B—C2—H2C | 107.8 | C9—C10—H10A | 120.3 |
C2—C3—C4 | 115.40 (18) | C11—C10—H10A | 120.3 |
C2—C3—H3A | 108.4 | C6—C11—C10 | 119.66 (18) |
C4—C3—H3A | 108.4 | C6—C11—H11A | 120.2 |
C2—C3—H3B | 108.4 | C10—C11—H11A | 120.2 |
C4—C3—H3B | 108.4 | ||
C1—C2—C3—C4 | −179.7 (2) | C6—C7—C8—C9 | −0.6 (3) |
C5—N1—C4—O1 | −0.9 (4) | C7—C8—C9—C10 | 0.1 (3) |
C5—N1—C4—C3 | 179.61 (19) | C7—C8—C9—N3 | 179.85 (18) |
C2—C3—C4—O1 | 16.9 (4) | O2—N3—C9—C10 | 175.4 (2) |
C2—C3—C4—N1 | −163.6 (2) | O3—N3—C9—C10 | −5.2 (3) |
C6—N2—C5—N1 | 176.16 (18) | O2—N3—C9—C8 | −4.4 (3) |
C6—N2—C5—S1 | −3.5 (3) | O3—N3—C9—C8 | 175.1 (2) |
C4—N1—C5—N2 | 8.5 (3) | C8—C9—C10—C11 | 0.2 (3) |
C4—N1—C5—S1 | −171.81 (16) | N3—C9—C10—C11 | −179.57 (19) |
C5—N2—C6—C11 | −2.9 (3) | C7—C6—C11—C10 | −0.6 (3) |
C5—N2—C6—C7 | 178.0 (2) | N2—C6—C11—C10 | −179.7 (2) |
C11—C6—C7—C8 | 0.9 (3) | C9—C10—C11—C6 | 0.1 (3) |
N2—C6—C7—C8 | −179.92 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.86 | 1.89 | 2.629 (2) | 143 |
N1—H1A···S1i | 0.86 | 2.62 | 3.4579 (18) | 164 |
C7—H7A···O2ii | 0.93 | 2.48 | 3.397 (3) | 168 |
Symmetry codes: (i) −x+2, −y−2, −z−1; (ii) −x, y−1/2, −z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C11H13N3O3S |
Mr | 267.30 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 4.9002 (12), 12.385 (3), 21.774 (5) |
β (°) | 100.727 (6) |
V (Å3) | 1298.3 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.25 |
Crystal size (mm) | 0.51 × 0.50 × 0.46 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.882, 0.892 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7048, 2540, 1933 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.128, 1.03 |
No. of reflections | 2540 |
No. of parameters | 164 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.16 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.86 | 1.89 | 2.629 (2) | 143 |
N1—H1A···S1i | 0.86 | 2.62 | 3.4579 (18) | 164 |
C7—H7A···O2ii | 0.93 | 2.48 | 3.397 (3) | 168 |
Symmetry codes: (i) −x+2, −y−2, −z−1; (ii) −x, y−1/2, −z−1/2. |
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The title compound is similar to the previously reported compound N-(4-methylbenzoyl)-N'-(4-nitrophenyl)thiourea (Yusof et al., 2006), except that the 4-methylbenzoyl group is replaced by a butanoyl group. The bond lengths and angles are comparable to those in that compound and to other thiourea derivatives (Yusof et al., 2007a,b). The central thiourea fragment (S1/C5/N1/N2) and phenyl ring (C6–C7) are essentially planar with maximum deviation of 0.013 (1) Å for atom N1, and the dihedral angle between them is 5.27 (8)°. An intramolecular hydrogen bond, N2—H2A···O1, forms a pseudo-six-membered ring (O1···H2A/N2/C5/N1/C4), and a relatively short intramolecular C—H···S contact is also observed (H11A···S1 = 2.56 Å, C11···S1 = 3.222 (2) Å, C11—H11A···S1 = 128 °). In the crystal structure, the molecules are linked into two-dimensional networks parallel to the bc planes via intermolecular N—H···S and C—H···O interactions (Fig. 2 & Table 1).