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organic compounds
The title compound {systematic name: 4-[2-({[(4-methoxybenzoyl)amino]carbonothioyl}amino)ethyl]morpholin-4-ium thiocyanate}, C15H22N3O3S+·NCS-, is a p-anisoylthiourea salt with a protonated morpholine group and a thiocyanate counter-anion. The morpholinium group has a chair conformation and the dihedral angle between the p-anisoyl group and the central thiourea N2CS group is 32.51 (8)°. The crystal structure is stablized by intra- and intermolecular hydrogen bonds.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805021124/is6100sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805021124/is6100Isup2.hkl |
CCDC reference: 282520
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.054
- wR factor = 0.125
- Data-to-parameter ratio = 15.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C16
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 4 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
Computing details top
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
4-[2-({[(4-methoxybenzoyl)amino]carbonothioyl}amino)ethyl]morpholin-4-ium
thiocyanate top
Crystal data top
C15H22N3O3S+·NCS− | F(000) = 808 |
Mr = 382.50 | Dx = 1.346 Mg m−3 |
Monoclinic, P21/n | Melting point = 417.1–419.0 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 9.0195 (18) Å | Cell parameters from 4016 reflections |
b = 10.402 (2) Å | θ = 2.0–25.5° |
c = 20.289 (4) Å | µ = 0.31 mm−1 |
β = 97.477 (3)° | T = 293 K |
V = 1887.3 (7) Å3 | Block, colourless |
Z = 4 | 0.42 × 0.33 × 0.25 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 3505 independent reflections |
Radiation source: fine-focus sealed tube | 3107 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
Detector resolution: 83.66 pixels mm-1 | θmax = 25.5°, θmin = 2.0° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −5→12 |
Tmin = 0.882, Tmax = 0.927 | l = −23→24 |
9351 measured 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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.125 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.17 | w = 1/[σ2(Fo2) + (0.0429P)2 + 0.9468P] where P = (Fo2 + 2Fc2)/3 |
3505 reflections | (Δ/σ)max < 0.001 |
231 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.42374 (7) | 0.60557 (8) | 0.07838 (3) | 0.0629 (2) | |
S2 | 0.54120 (11) | 0.11305 (10) | 0.15309 (5) | 0.0935 (3) | |
O1 | 0.91833 (19) | 0.5677 (2) | 0.15196 (9) | 0.0673 (6) | |
O2 | 1.1460 (2) | 0.11452 (18) | −0.01569 (10) | 0.0698 (5) | |
O3 | 0.2513 (2) | 0.37833 (19) | 0.31121 (10) | 0.0689 (5) | |
N1 | 0.70145 (19) | 0.5244 (2) | 0.08518 (9) | 0.0467 (5) | |
H1A | 0.6666 | 0.4867 | 0.0487 | 0.056* | |
N2 | 0.6548 (2) | 0.6593 (2) | 0.16978 (10) | 0.0485 (5) | |
H2A | 0.7490 | 0.6528 | 0.1829 | 0.058* | |
N3 | 0.4714 (2) | 0.54976 (19) | 0.27148 (9) | 0.0433 (4) | |
H3A | 0.512 (3) | 0.498 (2) | 0.2426 (11) | 0.043 (6)* | |
N4 | 0.6067 (3) | 0.3562 (3) | 0.20424 (14) | 0.0812 (8) | |
C1 | 0.8513 (3) | 0.2949 (2) | 0.04393 (12) | 0.0480 (6) | |
H1 | 0.7485 | 0.2870 | 0.0437 | 0.058* | |
C2 | 0.9283 (3) | 0.2017 (2) | 0.01522 (13) | 0.0546 (6) | |
H2 | 0.8775 | 0.1310 | −0.0046 | 0.066* | |
C3 | 1.0821 (3) | 0.2116 (2) | 0.01535 (12) | 0.0490 (6) | |
C4 | 1.1581 (3) | 0.3156 (2) | 0.04572 (12) | 0.0499 (6) | |
H4 | 1.2612 | 0.3223 | 0.0468 | 0.060* | |
C5 | 1.0797 (3) | 0.4090 (2) | 0.07432 (11) | 0.0481 (6) | |
H5 | 1.1310 | 0.4789 | 0.0947 | 0.058* | |
C6 | 0.9255 (2) | 0.4014 (2) | 0.07351 (10) | 0.0428 (5) | |
C7 | 0.8509 (2) | 0.5040 (2) | 0.10723 (11) | 0.0463 (5) | |
C8 | 0.6012 (2) | 0.5983 (2) | 0.11461 (11) | 0.0451 (5) | |
C9 | 0.5669 (3) | 0.7365 (2) | 0.20997 (12) | 0.0491 (6) | |
H9A | 0.4673 | 0.7484 | 0.1863 | 0.059* | |
H9B | 0.6127 | 0.8205 | 0.2172 | 0.059* | |
C10 | 0.5554 (3) | 0.6737 (2) | 0.27631 (12) | 0.0495 (6) | |
H10A | 0.6555 | 0.6582 | 0.2987 | 0.059* | |
H10B | 0.5065 | 0.7329 | 0.3035 | 0.059* | |
C11 | 0.4928 (3) | 0.4792 (3) | 0.33649 (13) | 0.0622 (7) | |
H11A | 0.4599 | 0.5329 | 0.3709 | 0.075* | |
H11B | 0.5981 | 0.4605 | 0.3488 | 0.075* | |
C12 | 0.4052 (3) | 0.3559 (3) | 0.33128 (14) | 0.0655 (7) | |
H12A | 0.4437 | 0.2996 | 0.2994 | 0.079* | |
H12B | 0.4179 | 0.3129 | 0.3741 | 0.079* | |
C13 | 0.2303 (3) | 0.4387 (3) | 0.24798 (15) | 0.0619 (7) | |
H13A | 0.1242 | 0.4509 | 0.2341 | 0.074* | |
H13B | 0.2688 | 0.3833 | 0.2157 | 0.074* | |
C14 | 0.3079 (3) | 0.5663 (2) | 0.24929 (13) | 0.0511 (6) | |
H14A | 0.2932 | 0.6043 | 0.2053 | 0.061* | |
H14B | 0.2655 | 0.6239 | 0.2795 | 0.061* | |
C15 | 1.3034 (3) | 0.1150 (3) | −0.01619 (17) | 0.0780 (9) | |
H15A | 1.3319 | 0.1913 | −0.0380 | 0.117* | |
H15B | 1.3319 | 0.0406 | −0.0396 | 0.117* | |
H15C | 1.3527 | 0.1132 | 0.0287 | 0.117* | |
C16 | 0.5774 (3) | 0.2561 (3) | 0.18190 (13) | 0.0572 (7) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0373 (3) | 0.0891 (6) | 0.0599 (4) | 0.0043 (3) | −0.0023 (3) | −0.0194 (4) |
S2 | 0.0891 (6) | 0.0838 (6) | 0.1051 (7) | −0.0169 (5) | 0.0034 (5) | −0.0262 (5) |
O1 | 0.0406 (9) | 0.0894 (14) | 0.0693 (12) | 0.0028 (9) | −0.0033 (8) | −0.0320 (11) |
O2 | 0.0615 (12) | 0.0612 (12) | 0.0865 (14) | 0.0076 (9) | 0.0083 (10) | −0.0194 (11) |
O3 | 0.0629 (12) | 0.0653 (12) | 0.0797 (13) | −0.0058 (10) | 0.0139 (10) | 0.0201 (10) |
N1 | 0.0374 (10) | 0.0617 (13) | 0.0402 (10) | −0.0013 (9) | 0.0019 (8) | −0.0102 (9) |
N2 | 0.0349 (10) | 0.0577 (12) | 0.0522 (11) | −0.0031 (9) | 0.0035 (8) | −0.0096 (10) |
N3 | 0.0416 (10) | 0.0446 (11) | 0.0431 (10) | 0.0025 (9) | 0.0031 (8) | −0.0052 (9) |
N4 | 0.089 (2) | 0.0598 (16) | 0.098 (2) | 0.0193 (14) | 0.0215 (15) | −0.0110 (15) |
C1 | 0.0397 (12) | 0.0523 (14) | 0.0505 (13) | −0.0039 (11) | 0.0007 (10) | 0.0048 (11) |
C2 | 0.0527 (15) | 0.0473 (14) | 0.0617 (15) | −0.0064 (12) | −0.0006 (12) | −0.0037 (12) |
C3 | 0.0512 (14) | 0.0471 (13) | 0.0483 (13) | 0.0046 (11) | 0.0051 (10) | 0.0009 (11) |
C4 | 0.0391 (12) | 0.0595 (15) | 0.0510 (14) | 0.0002 (11) | 0.0057 (10) | −0.0010 (12) |
C5 | 0.0421 (13) | 0.0533 (14) | 0.0478 (13) | −0.0045 (11) | 0.0016 (10) | −0.0066 (11) |
C6 | 0.0396 (12) | 0.0521 (14) | 0.0360 (11) | −0.0003 (10) | 0.0024 (9) | 0.0043 (10) |
C7 | 0.0383 (12) | 0.0590 (15) | 0.0411 (12) | −0.0031 (11) | 0.0034 (9) | −0.0023 (11) |
C8 | 0.0397 (12) | 0.0506 (14) | 0.0450 (12) | −0.0052 (10) | 0.0059 (10) | −0.0018 (11) |
C9 | 0.0446 (13) | 0.0449 (13) | 0.0582 (15) | −0.0024 (11) | 0.0083 (11) | −0.0099 (11) |
C10 | 0.0454 (13) | 0.0496 (14) | 0.0527 (14) | −0.0048 (11) | 0.0039 (10) | −0.0152 (11) |
C11 | 0.0646 (16) | 0.0712 (18) | 0.0475 (14) | 0.0012 (14) | −0.0053 (12) | 0.0067 (13) |
C12 | 0.0726 (19) | 0.0615 (17) | 0.0606 (17) | 0.0026 (14) | 0.0018 (14) | 0.0176 (14) |
C13 | 0.0482 (15) | 0.0589 (16) | 0.0752 (18) | −0.0071 (12) | −0.0044 (12) | 0.0126 (14) |
C14 | 0.0397 (12) | 0.0500 (14) | 0.0626 (15) | 0.0025 (11) | 0.0029 (11) | 0.0064 (12) |
C15 | 0.0658 (19) | 0.078 (2) | 0.093 (2) | 0.0114 (16) | 0.0189 (16) | −0.0168 (18) |
C16 | 0.0500 (15) | 0.0683 (19) | 0.0552 (15) | 0.0159 (13) | 0.0137 (11) | 0.0060 (14) |
Geometric parameters (Å, º) top
S1—C8 | 1.674 (2) | C4—C5 | 1.373 (3) |
S2—C16 | 1.617 (3) | C4—H4 | 0.9300 |
O1—C7 | 1.220 (3) | C5—C6 | 1.391 (3) |
O2—C3 | 1.358 (3) | C5—H5 | 0.9300 |
O2—C15 | 1.421 (3) | C6—C7 | 1.476 (3) |
O3—C12 | 1.414 (3) | C9—C10 | 1.511 (3) |
O3—C13 | 1.419 (3) | C9—H9A | 0.9700 |
N1—C8 | 1.380 (3) | C9—H9B | 0.9700 |
N1—C7 | 1.381 (3) | C10—H10A | 0.9700 |
N1—H1A | 0.8600 | C10—H10B | 0.9700 |
N2—C8 | 1.322 (3) | C11—C12 | 1.503 (4) |
N2—C9 | 1.451 (3) | C11—H11A | 0.9700 |
N2—H2A | 0.8600 | C11—H11B | 0.9700 |
N3—C10 | 1.492 (3) | C12—H12A | 0.9700 |
N3—C14 | 1.494 (3) | C12—H12B | 0.9700 |
N3—C11 | 1.500 (3) | C13—C14 | 1.499 (3) |
N3—H3A | 0.91 (2) | C13—H13A | 0.9700 |
N4—C16 | 1.152 (4) | C13—H13B | 0.9700 |
C1—C2 | 1.367 (4) | C14—H14A | 0.9700 |
C1—C6 | 1.390 (3) | C14—H14B | 0.9700 |
C1—H1 | 0.9300 | C15—H15A | 0.9600 |
C2—C3 | 1.390 (3) | C15—H15B | 0.9600 |
C2—H2 | 0.9300 | C15—H15C | 0.9600 |
C3—C4 | 1.382 (3) | ||
C3—O2—C15 | 119.1 (2) | N2—C9—H9B | 109.3 |
C12—O3—C13 | 110.1 (2) | C10—C9—H9B | 109.3 |
C8—N1—C7 | 127.79 (19) | H9A—C9—H9B | 108.0 |
C8—N1—H1A | 116.1 | N3—C10—C9 | 114.05 (19) |
C7—N1—H1A | 116.1 | N3—C10—H10A | 108.7 |
C8—N2—C9 | 125.1 (2) | C9—C10—H10A | 108.7 |
C8—N2—H2A | 117.4 | N3—C10—H10B | 108.7 |
C9—N2—H2A | 117.4 | C9—C10—H10B | 108.7 |
C10—N3—C14 | 113.13 (19) | H10A—C10—H10B | 107.6 |
C10—N3—C11 | 111.03 (19) | N3—C11—C12 | 110.5 (2) |
C14—N3—C11 | 109.29 (19) | N3—C11—H11A | 109.6 |
C10—N3—H3A | 107.7 (15) | C12—C11—H11A | 109.6 |
C14—N3—H3A | 110.1 (14) | N3—C11—H11B | 109.6 |
C11—N3—H3A | 105.3 (14) | C12—C11—H11B | 109.6 |
C2—C1—C6 | 120.4 (2) | H11A—C11—H11B | 108.1 |
C2—C1—H1 | 119.8 | O3—C12—C11 | 111.5 (2) |
C6—C1—H1 | 119.8 | O3—C12—H12A | 109.3 |
C1—C2—C3 | 120.6 (2) | C11—C12—H12A | 109.3 |
C1—C2—H2 | 119.7 | O3—C12—H12B | 109.3 |
C3—C2—H2 | 119.7 | C11—C12—H12B | 109.3 |
O2—C3—C4 | 124.9 (2) | H12A—C12—H12B | 108.0 |
O2—C3—C2 | 115.3 (2) | O3—C13—C14 | 111.6 (2) |
C4—C3—C2 | 119.7 (2) | O3—C13—H13A | 109.3 |
C5—C4—C3 | 119.3 (2) | C14—C13—H13A | 109.3 |
C5—C4—H4 | 120.4 | O3—C13—H13B | 109.3 |
C3—C4—H4 | 120.4 | C14—C13—H13B | 109.3 |
C4—C5—C6 | 121.6 (2) | H13A—C13—H13B | 108.0 |
C4—C5—H5 | 119.2 | N3—C14—C13 | 110.1 (2) |
C6—C5—H5 | 119.2 | N3—C14—H14A | 109.6 |
C1—C6—C5 | 118.4 (2) | C13—C14—H14A | 109.6 |
C1—C6—C7 | 123.6 (2) | N3—C14—H14B | 109.6 |
C5—C6—C7 | 118.0 (2) | C13—C14—H14B | 109.6 |
O1—C7—N1 | 121.9 (2) | H14A—C14—H14B | 108.2 |
O1—C7—C6 | 121.6 (2) | O2—C15—H15A | 109.5 |
N1—C7—C6 | 116.49 (19) | O2—C15—H15B | 109.5 |
N2—C8—N1 | 116.5 (2) | H15A—C15—H15B | 109.5 |
N2—C8—S1 | 124.97 (18) | O2—C15—H15C | 109.5 |
N1—C8—S1 | 118.55 (17) | H15A—C15—H15C | 109.5 |
N2—C9—C10 | 111.6 (2) | H15B—C15—H15C | 109.5 |
N2—C9—H9A | 109.3 | N4—C16—S2 | 177.5 (3) |
C10—C9—H9A | 109.3 | ||
C6—C1—C2—C3 | 0.3 (4) | C5—C6—C7—N1 | 155.4 (2) |
C15—O2—C3—C4 | 2.0 (4) | C9—N2—C8—N1 | −176.8 (2) |
C15—O2—C3—C2 | −178.1 (3) | C9—N2—C8—S1 | 3.8 (4) |
C1—C2—C3—O2 | −178.8 (2) | C7—N1—C8—N2 | 1.7 (4) |
C1—C2—C3—C4 | 1.0 (4) | C7—N1—C8—S1 | −178.91 (19) |
O2—C3—C4—C5 | 178.7 (2) | C8—N2—C9—C10 | 111.2 (3) |
C2—C3—C4—C5 | −1.2 (4) | C14—N3—C10—C9 | −69.1 (3) |
C3—C4—C5—C6 | 0.0 (4) | C11—N3—C10—C9 | 167.5 (2) |
C2—C1—C6—C5 | −1.4 (3) | N2—C9—C10—N3 | −65.3 (3) |
C2—C1—C6—C7 | −178.1 (2) | C10—N3—C11—C12 | 178.9 (2) |
C4—C5—C6—C1 | 1.2 (3) | C14—N3—C11—C12 | 53.4 (3) |
C4—C5—C6—C7 | 178.2 (2) | C13—O3—C12—C11 | 60.3 (3) |
C8—N1—C7—O1 | −11.9 (4) | N3—C11—C12—O3 | −57.3 (3) |
C8—N1—C7—C6 | 168.6 (2) | C12—O3—C13—C14 | −60.9 (3) |
C1—C6—C7—O1 | 152.6 (2) | C10—N3—C14—C13 | −178.0 (2) |
C5—C6—C7—O1 | −24.2 (3) | C11—N3—C14—C13 | −53.7 (3) |
C1—C6—C7—N1 | −27.9 (3) | O3—C13—C14—N3 | 58.2 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.86 | 1.94 | 2.629 (3) | 136 |
C9—H9A···S1 | 0.97 | 2.63 | 3.123 (3) | 112 |
N3—H3A···N4 | 0.91 (2) | 1.92 (2) | 2.800 (4) | 163 (2) |
N1—H1A···S1i | 0.86 | 2.77 | 3.625 (2) | 171 |
C2—H2···O2ii | 0.93 | 2.60 | 3.357 (3) | 139 |
C9—H9A···O3iii | 0.97 | 2.40 | 3.206 (3) | 141 |
C10—H10A···S2iv | 0.97 | 2.82 | 3.786 (3) | 172 |
C15—H15C···S2v | 0.96 | 2.85 | 3.805 (4) | 171 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+2, −y, −z; (iii) −x+1/2, y+1/2, −z+1/2; (iv) −x+3/2, y+1/2, −z+1/2; (v) x+1, y, z. |
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