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The title compound, C
11H
20O
4N
2S, has a planar skeleton and its crystal structure is stabilized by extensive intermolecular (N—H
S) and intramolecular (N—H
O and C—H
O) hydrogen-bonding interactions.
Supporting information
CCDC reference: 206795
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.045
- wR factor = 0.057
- Data-to-parameter ratio = 13.4
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: SMART (Bruker, 1996); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: TEXSAN (Molecular Structure corporation, 1992); software used to prepare material for publication: TEXSAN.
Crystal data top
C11H20N2O4S | Z = 2 |
Mr = 276.35 | F(000) = 296 |
Triclinic, P1 | Dx = 1.184 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.7107 Å |
a = 6.171 (2) Å | Cell parameters from 31 reflections |
b = 11.334 (3) Å | θ = >0.0–28.0° |
c = 11.653 (3) Å | µ = 0.22 mm−1 |
α = 81.25 (1)° | T = 298 K |
β = 87.31 (1)° | Block, colourless |
γ = 74.27 (1)° | 0.39 × 0.15 × 0.08 mm |
V = 775.4 (4) Å3 | |
Data collection top
Bruker SMART 1K CCD area-detector diffractometer | 3344 independent reflections |
Radiation source: X-ray tube | 2188 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
φ and ω scans | θmax = 27°, θmin = 2.5° |
Absorption correction: multi-scan SADABS (Bruker, 1997) | h = 0→7 |
Tmin = 0.960, Tmax = 0.984 | k = −13→14 |
4811 measured reflections | l = −14→14 |
Refinement top
Refinement on F | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.045 | Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo) + 0.0005(Fo)2] |
wR(F2) = 0.057 | (Δ/σ)max < 0.001 |
S = 1.57 | Δρmax = 0.27 e Å−3 |
2188 reflections | Δρmin = −0.16 e Å−3 |
163 parameters | |
Special details top
Refinement. Hydrogen atoms were included in the riding model approximation. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.3416 (1) | 0.46403 (6) | 0.35133 (5) | 0.0723 (2) | |
O1 | −0.0711 (3) | 0.1878 (1) | 0.3847 (1) | 0.0595 (5) | |
O2 | 0.1220 (3) | 0.2897 (2) | 0.2535 (2) | 0.0842 (7) | |
O3 | 0.3157 (3) | 0.3592 (1) | 0.7606 (1) | 0.0636 (5) | |
O4 | 0.1290 (3) | 0.2465 (2) | 0.6795 (1) | 0.0704 (6) | |
N1 | 0.1145 (3) | 0.3021 (2) | 0.4496 (2) | 0.0597 (6) | |
N2 | 0.2920 (3) | 0.3867 (2) | 0.5710 (2) | 0.0595 (6) | |
C1 | −0.2676 (5) | 0.1982 (3) | 0.2029 (2) | 0.0809 (10) | |
C2 | 0.0682 (5) | 0.0223 (3) | 0.2682 (3) | 0.093 (1) | |
C3 | −0.2916 (5) | 0.0517 (2) | 0.3803 (2) | 0.0755 (9) | |
C4 | −0.1385 (4) | 0.1142 (2) | 0.3043 (2) | 0.0587 (7) | |
C5 | 0.0600 (4) | 0.2630 (2) | 0.3487 (2) | 0.0579 (7) | |
C6 | 0.2455 (4) | 0.3799 (2) | 0.4579 (2) | 0.0535 (7) | |
C7 | 0.3783 (5) | 0.3898 (3) | 0.9475 (2) | 0.0813 (10) | |
C8 | 0.3980 (6) | 0.1766 (3) | 0.9081 (3) | 0.110 (1) | |
C9 | 0.0285 (5) | 0.3381 (3) | 0.9062 (2) | 0.091 (1) | |
C10 | 0.2761 (4) | 0.3121 (2) | 0.8828 (2) | 0.0586 (7) | |
C11 | 0.2348 (4) | 0.3222 (2) | 0.6732 (2) | 0.0555 (7) | |
H1N | 0.0581 | 0.2735 | 0.5143 | 0.0717 | |
H1A | −0.1761 | 0.2461 | 0.1620 | 0.0971 | |
H1B | −0.3086 | 0.1497 | 0.1523 | 0.0971 | |
H1C | −0.3996 | 0.2518 | 0.2304 | 0.0971 | |
H2N | 0.3682 | 0.4391 | 0.5793 | 0.0714 | |
H2A | 0.1381 | −0.0309 | 0.3350 | 0.1121 | |
H2B | 0.0272 | −0.0254 | 0.2168 | 0.1121 | |
H2C | 0.1702 | 0.0651 | 0.2301 | 0.1121 | |
H3A | −0.4146 | 0.1128 | 0.4061 | 0.0906 | |
H3B | −0.3465 | 0.0012 | 0.3372 | 0.0906 | |
H3C | −0.2101 | 0.0017 | 0.4455 | 0.0906 | |
H7A | 0.3627 | 0.3669 | 1.0288 | 0.0975 | |
H7B | 0.5334 | 0.3763 | 0.9280 | 0.0975 | |
H7C | 0.3029 | 0.4749 | 0.9265 | 0.0975 | |
H8A | 0.3719 | 0.1461 | 0.9866 | 0.1320 | |
H8B | 0.3441 | 0.1321 | 0.8581 | 0.1320 | |
H8C | 0.5548 | 0.1662 | 0.8954 | 0.1320 | |
H9A | −0.0383 | 0.4249 | 0.8915 | 0.1097 | |
H9B | −0.0369 | 0.2979 | 0.8569 | 0.1097 | |
H9C | 0.0035 | 0.3082 | 0.9849 | 0.1097 | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0982 (5) | 0.0829 (5) | 0.0520 (4) | −0.0559 (4) | −0.0008 (3) | −0.0013 (3) |
O1 | 0.077 (1) | 0.0673 (10) | 0.0470 (9) | −0.0403 (9) | −0.0046 (7) | −0.0074 (7) |
O2 | 0.112 (1) | 0.116 (2) | 0.050 (1) | −0.073 (1) | 0.0067 (9) | −0.0140 (9) |
O3 | 0.079 (1) | 0.082 (1) | 0.0459 (9) | −0.0475 (9) | 0.0074 (7) | −0.0172 (8) |
O4 | 0.101 (1) | 0.075 (1) | 0.0538 (10) | −0.056 (1) | 0.0000 (8) | −0.0064 (8) |
N1 | 0.079 (1) | 0.069 (1) | 0.046 (1) | −0.043 (1) | 0.0024 (9) | −0.0100 (8) |
N2 | 0.080 (1) | 0.066 (1) | 0.048 (1) | −0.043 (1) | 0.0031 (9) | −0.0121 (9) |
C1 | 0.086 (2) | 0.102 (2) | 0.063 (2) | −0.041 (2) | −0.017 (1) | −0.005 (1) |
C2 | 0.085 (2) | 0.093 (2) | 0.113 (3) | −0.027 (2) | 0.000 (2) | −0.044 (2) |
C3 | 0.087 (2) | 0.080 (2) | 0.074 (2) | −0.047 (2) | −0.009 (1) | −0.009 (1) |
C4 | 0.066 (2) | 0.063 (1) | 0.056 (1) | −0.028 (1) | −0.009 (1) | −0.015 (1) |
C5 | 0.068 (2) | 0.065 (1) | 0.048 (1) | −0.029 (1) | −0.002 (1) | −0.008 (1) |
C6 | 0.062 (1) | 0.056 (1) | 0.050 (1) | −0.025 (1) | 0.0003 (10) | −0.0107 (10) |
C7 | 0.090 (2) | 0.105 (2) | 0.061 (2) | −0.040 (2) | −0.002 (1) | −0.025 (1) |
C8 | 0.149 (3) | 0.083 (2) | 0.089 (2) | −0.012 (2) | −0.035 (2) | −0.009 (2) |
C9 | 0.081 (2) | 0.143 (3) | 0.058 (2) | −0.046 (2) | 0.012 (1) | −0.014 (2) |
C10 | 0.065 (1) | 0.070 (2) | 0.045 (1) | −0.024 (1) | 0.001 (1) | −0.009 (1) |
C11 | 0.066 (1) | 0.060 (1) | 0.049 (1) | −0.029 (1) | 0.003 (1) | −0.012 (1) |
Geometric parameters (Å, º) top
S1—C6 | 1.637 (2) | C2—H2B | 0.950 |
O1—C4 | 1.487 (3) | C2—H2C | 0.950 |
O1—C5 | 1.337 (3) | C3—C4 | 1.508 (4) |
O2—C5 | 1.179 (3) | C3—H3A | 0.950 |
O3—C10 | 1.477 (3) | C3—H3B | 0.950 |
O3—C11 | 1.323 (3) | C3—H3C | 0.950 |
O4—C11 | 1.203 (3) | C7—C10 | 1.514 (4) |
N1—C5 | 1.402 (3) | C7—H7A | 0.950 |
N1—C6 | 1.364 (3) | C7—H7B | 0.950 |
N1—H1N | 0.870 | C7—H7C | 0.950 |
N2—C6 | 1.380 (3) | C8—C10 | 1.505 (4) |
N2—C11 | 1.383 (3) | C8—H8A | 0.950 |
N2—H2N | 0.870 | C8—H8B | 0.950 |
C1—C4 | 1.508 (3) | C8—H8C | 0.950 |
C1—H1A | 0.950 | C9—C10 | 1.495 (4) |
C1—H1B | 0.950 | C9—H9A | 0.950 |
C1—H1C | 0.950 | C9—H9B | 0.950 |
C2—C4 | 1.500 (4) | C9—H9C | 0.950 |
C2—H2A | 0.950 | | |
| | | |
C4—O1—C5 | 121.1 (2) | O1—C5—N1 | 105.3 (2) |
C10—O3—C11 | 121.9 (2) | O2—C5—N1 | 126.5 (2) |
C5—N1—C6 | 127.5 (2) | S1—C6—N1 | 127.3 (2) |
C5—N1—H1N | 116.2 | S1—C6—N2 | 119.5 (2) |
C6—N1—H1N | 116.2 | N1—C6—N2 | 113.2 (2) |
C6—N2—C11 | 129.4 (2) | C10—C7—H7A | 109.5 |
C6—N2—H2N | 115.3 | C10—C7—H7B | 109.5 |
C11—N2—H2N | 115.3 | C10—C7—H7C | 109.5 |
C4—C1—H1A | 109.5 | H7A—C7—H7B | 109.5 |
C4—C1—H1B | 109.5 | H7A—C7—H7C | 109.5 |
C4—C1—H1C | 109.5 | H7B—C7—H7C | 109.5 |
H1A—C1—H1B | 109.5 | C10—C8—H8A | 109.5 |
H1A—C1—H1C | 109.5 | C10—C8—H8B | 109.5 |
H1B—C1—H1C | 109.5 | C10—C8—H8C | 109.5 |
C4—C2—H2A | 109.5 | H8A—C8—H8B | 109.5 |
C4—C2—H2B | 109.5 | H8A—C8—H8C | 109.5 |
C4—C2—H2C | 109.5 | H8B—C8—H8C | 109.5 |
H2A—C2—H2B | 109.5 | C10—C9—H9A | 109.5 |
H2A—C2—H2C | 109.5 | C10—C9—H9B | 109.5 |
H2B—C2—H2C | 109.5 | C10—C9—H9C | 109.5 |
C4—C3—H3A | 109.5 | H9A—C9—H9B | 109.5 |
C4—C3—H3B | 109.5 | H9A—C9—H9C | 109.5 |
C4—C3—H3C | 109.5 | H9B—C9—H9C | 109.5 |
H3A—C3—H3B | 109.5 | O3—C10—C7 | 102.0 (2) |
H3A—C3—H3C | 109.5 | O3—C10—C8 | 109.4 (2) |
H3B—C3—H3C | 109.5 | O3—C10—C9 | 109.6 (2) |
O1—C4—C1 | 110.6 (2) | C7—C10—C8 | 111.6 (2) |
O1—C4—C2 | 108.7 (2) | C7—C10—C9 | 110.4 (2) |
O1—C4—C3 | 101.8 (2) | C8—C10—C9 | 113.2 (3) |
C1—C4—C2 | 113.1 (2) | O3—C11—O4 | 127.0 (2) |
C1—C4—C3 | 110.2 (2) | O3—C11—N2 | 107.9 (2) |
C2—C4—C3 | 111.8 (2) | O4—C11—N2 | 125.0 (2) |
O1—C5—O2 | 128.2 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O4 | 0.87 | 1.96 | 2.658 (3) | 137 |
N2—H2N···S1i | 0.87 | 2.56 | 3.395 (2) | 162 |
C1—H1A···O2 | 0.95 | 2.37 | 2.980 (4) | 122 |
C2—H2C···O2 | 0.95 | 2.54 | 3.117 (4) | 119 |
C8—H8B···O4 | 0.95 | 2.51 | 3.093 (5) | 120 |
C9—H9B···O4 | 0.95 | 2.35 | 2.962 (3) | 122 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
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