The title compound, C9H18N2O6S, is the first example of a simple monosulfonamide derivative of a hydrazine-1,2-dicarboxylate. The molecule adopts an s-cis conformation about the amide bond bearing the methylsulfonyl group.
Supporting information
CCDC reference: 643029
Key indicators
- Single-crystal X-ray study
- T = 200 K
- Mean (C-C) = 0.003 Å
- R factor = 0.030
- wR factor = 0.089
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.71 Ratio
Alert level C
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.68 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C3
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
2 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
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: COLLECT (Nonius, 1997); cell refinement: DENZO and SCALEPACK; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEPII (Johnson, 1976) in TEXSAN (Molecular Structure Corporation,
1997); software used to prepare material for publication: CRYSTALS.
Diisopropyl 1-(methylsulfonyl)hydrazine-1,2-dicarboxylate
top
Crystal data top
C9H18N2O6S | F(000) = 600 |
Mr = 282.32 | Dx = 1.301 Mg m−3 |
Monoclinic, P21/c | Melting point: 375 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 9.0845 (2) Å | Cell parameters from 18147 reflections |
b = 17.1465 (4) Å | θ = 3–27.5° |
c = 9.9094 (2) Å | µ = 0.24 mm−1 |
β = 110.9720 (13)° | T = 200 K |
V = 1441.31 (6) Å3 | Plate, colourless |
Z = 4 | 0.43 × 0.40 × 0.08 mm |
Data collection top
Nonius KappaCCD area-detector diffractometer | 2459 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
φ and ω scans | θmax = 27.5°, θmin = 2.7° |
Absorption correction: integration [Gaussian method (Coppens, 1970) implemented in MAXUS (Mackay et
al., 1999)] | h = −11→11 |
Tmin = 0.908, Tmax = 0.976 | k = −22→22 |
28645 measured reflections | l = −12→12 |
3285 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.030 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.089 | w = [1-(Fo-Fc)2/36σ2(F)]2/
[28.0T0(x) + 45.0T1(x) + 26.4T2(x) + 10.7T3(x) + 2.11T4(x)],
where Ti are the Chebychev polynomials and
x = Fc/Fmax (Carruthers & Watkin, 1979; Prince, 1982) |
S = 0.94 | (Δ/σ)max = 0.006 |
3280 reflections | Δρmax = 0.24 e Å−3 |
217 parameters | Δρmin = −0.37 e Å−3 |
9 restraints | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 0.31562 (4) | 0.074731 (19) | 0.28286 (4) | 0.0323 | |
O1 | 0.40162 (14) | 0.00998 (6) | 0.26002 (12) | 0.0447 | |
O2 | 0.15985 (13) | 0.08964 (7) | 0.18433 (13) | 0.0504 | |
O3 | 0.64864 (12) | 0.11425 (6) | 0.44293 (13) | 0.0459 | |
O4 | 0.63078 (12) | 0.23343 (6) | 0.34051 (12) | 0.0421 | |
O5 | 0.32493 (13) | 0.25977 (6) | 0.43007 (10) | 0.0390 | |
O6 | 0.22089 (11) | 0.33479 (6) | 0.22914 (10) | 0.0340 | |
N1 | 0.41766 (12) | 0.15654 (6) | 0.27257 (12) | 0.0286 | |
N2 | 0.33078 (13) | 0.22223 (6) | 0.21338 (11) | 0.0288 | |
C1 | 0.3172 (2) | 0.07203 (9) | 0.45996 (17) | 0.0398 | |
C2 | 0.57698 (15) | 0.16467 (8) | 0.36179 (14) | 0.0323 | |
C3 | 0.7925 (2) | 0.25315 (11) | 0.4343 (2) | 0.0515 | |
C4 | 0.9076 (2) | 0.22050 (18) | 0.3722 (3) | 0.0775 | |
C5 | 0.7941 (4) | 0.34027 (15) | 0.4469 (5) | 0.1041 | |
C6 | 0.29449 (14) | 0.27250 (7) | 0.30223 (13) | 0.0279 | |
C7 | 0.18280 (17) | 0.39724 (8) | 0.31366 (16) | 0.0369 | |
C8 | 0.3273 (2) | 0.44542 (11) | 0.3870 (2) | 0.0535 | |
C9 | 0.0492 (2) | 0.44218 (12) | 0.2065 (2) | 0.0586 | |
H1 | 0.3197 (19) | 0.2329 (9) | 0.1286 (19) | 0.0340* | |
H11 | 0.273 (2) | 0.0211 (11) | 0.470 (2) | 0.0480* | |
H12 | 0.421 (2) | 0.0762 (10) | 0.525 (2) | 0.0480* | |
H13 | 0.256 (2) | 0.1139 (11) | 0.474 (2) | 0.0480* | |
H31 | 0.810 (2) | 0.2276 (12) | 0.526 (2) | 0.0620* | |
H41 | 1.013 (2) | 0.2349 (12) | 0.437 (2) | 0.0930* | |
H42 | 0.883 (2) | 0.2474 (11) | 0.282 (2) | 0.0930* | |
H43 | 0.895 (2) | 0.1634 (10) | 0.362 (2) | 0.0930* | |
H51 | 0.895 (4) | 0.3557 (19) | 0.502 (4) | 0.1250* | |
H52 | 0.719 (4) | 0.357 (2) | 0.506 (4) | 0.1250* | |
H53 | 0.761 (4) | 0.362 (2) | 0.353 (4) | 0.1250* | |
H71 | 0.147 (2) | 0.3713 (11) | 0.384 (2) | 0.0440* | |
H81 | 0.303 (3) | 0.4859 (13) | 0.443 (2) | 0.0640* | |
H82 | 0.414 (3) | 0.4147 (12) | 0.454 (2) | 0.0640* | |
H83 | 0.361 (3) | 0.4659 (12) | 0.318 (3) | 0.0640* | |
H91 | 0.017 (3) | 0.4862 (13) | 0.256 (2) | 0.0700* | |
H92 | 0.084 (3) | 0.4672 (13) | 0.139 (3) | 0.0700* | |
H93 | −0.044 (3) | 0.4064 (13) | 0.159 (3) | 0.0700* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.03263 (17) | 0.03094 (17) | 0.03254 (17) | −0.00195 (12) | 0.01085 (13) | 0.00093 (12) |
O1 | 0.0578 (6) | 0.0312 (5) | 0.0497 (6) | 0.0006 (5) | 0.0249 (5) | −0.0053 (4) |
O2 | 0.0333 (5) | 0.0567 (7) | 0.0506 (7) | −0.0084 (5) | 0.0021 (5) | 0.0112 (5) |
O3 | 0.0346 (5) | 0.0424 (6) | 0.0518 (6) | 0.0019 (4) | 0.0049 (5) | 0.0162 (5) |
O4 | 0.0340 (5) | 0.0390 (5) | 0.0461 (6) | −0.0065 (4) | 0.0057 (4) | 0.0111 (4) |
O5 | 0.0578 (6) | 0.0389 (5) | 0.0242 (5) | 0.0029 (4) | 0.0196 (4) | 0.0018 (4) |
O6 | 0.0432 (5) | 0.0318 (5) | 0.0283 (4) | 0.0095 (4) | 0.0145 (4) | 0.0016 (4) |
N1 | 0.0287 (5) | 0.0277 (5) | 0.0289 (5) | 0.0020 (4) | 0.0098 (4) | 0.0038 (4) |
N2 | 0.0362 (5) | 0.0309 (5) | 0.0206 (5) | 0.0075 (4) | 0.0116 (4) | 0.0047 (4) |
C1 | 0.0508 (9) | 0.0348 (7) | 0.0410 (7) | 0.0011 (6) | 0.0251 (7) | 0.0067 (6) |
C2 | 0.0309 (6) | 0.0335 (6) | 0.0321 (6) | 0.0004 (5) | 0.0107 (5) | 0.0035 (5) |
C3 | 0.0371 (8) | 0.0566 (10) | 0.0502 (9) | −0.0140 (7) | 0.0026 (7) | 0.0092 (8) |
C4 | 0.0438 (10) | 0.112 (2) | 0.0753 (14) | −0.0071 (11) | 0.0201 (10) | 0.0164 (13) |
C5 | 0.0698 (16) | 0.0560 (14) | 0.150 (3) | −0.0266 (12) | −0.0048 (18) | −0.0041 (16) |
C6 | 0.0297 (6) | 0.0308 (6) | 0.0245 (6) | −0.0007 (5) | 0.0110 (5) | 0.0010 (4) |
C7 | 0.0434 (8) | 0.0324 (6) | 0.0415 (7) | 0.0032 (6) | 0.0232 (6) | −0.0045 (6) |
C8 | 0.0576 (10) | 0.0459 (9) | 0.0609 (11) | −0.0121 (8) | 0.0260 (9) | −0.0146 (8) |
C9 | 0.0590 (11) | 0.0504 (10) | 0.0641 (12) | 0.0232 (9) | 0.0193 (9) | −0.0022 (9) |
Geometric parameters (Å, º) top
S1—O1 | 1.4216 (11) | C3—C5 | 1.499 (3) |
S1—O2 | 1.4255 (11) | C3—H31 | 0.97 (2) |
S1—N1 | 1.7044 (11) | C4—H41 | 0.975 (16) |
S1—C1 | 1.7503 (15) | C4—H42 | 0.956 (16) |
O3—C2 | 1.2013 (17) | C4—H43 | 0.987 (16) |
O4—C2 | 1.3218 (16) | C5—H51 | 0.92 (4) |
O4—C3 | 1.4689 (18) | C5—H52 | 1.08 (3) |
O5—C6 | 1.2159 (15) | C5—H53 | 0.94 (4) |
O6—C6 | 1.3287 (15) | C7—C8 | 1.500 (2) |
O6—C7 | 1.4749 (15) | C7—C9 | 1.507 (2) |
N1—N2 | 1.3800 (14) | C7—H71 | 0.970 (18) |
N1—C2 | 1.4071 (16) | C8—H81 | 0.96 (2) |
N2—C6 | 1.3544 (16) | C8—H82 | 0.99 (2) |
N2—H1 | 0.830 (17) | C8—H83 | 0.92 (2) |
C1—H11 | 0.983 (19) | C9—H91 | 1.00 (2) |
C1—H12 | 0.93 (2) | C9—H92 | 0.94 (2) |
C1—H13 | 0.947 (19) | C9—H93 | 1.02 (2) |
C3—C4 | 1.499 (3) | | |
| | | |
O1···C1i | 3.336 (2) | O3···C1i | 3.318 (2) |
O1···C8ii | 3.461 (3) | O5···N2vi | 2.806 (2) |
O1···C8iii | 3.594 (2) | O5···N1vi | 3.499 (2) |
O2···C5iv | 3.525 (3) | O6···C1iii | 3.479 (2) |
O2···C9v | 3.555 (2) | | |
| | | |
O1—S1—O2 | 119.89 (7) | H41—C4—H42 | 109.6 (14) |
O1—S1—N1 | 106.95 (6) | C3—C4—H43 | 109.9 (12) |
O2—S1—N1 | 103.84 (6) | H41—C4—H43 | 111.9 (14) |
O1—S1—C1 | 109.34 (7) | H42—C4—H43 | 113.6 (14) |
O2—S1—C1 | 109.97 (8) | C3—C5—H51 | 108 (2) |
N1—S1—C1 | 105.79 (7) | C3—C5—H52 | 109.0 (19) |
C2—O4—C3 | 116.59 (11) | H51—C5—H52 | 107 (3) |
C6—O6—C7 | 116.66 (10) | C3—C5—H53 | 108 (2) |
S1—N1—N2 | 117.17 (8) | H51—C5—H53 | 112 (3) |
S1—N1—C2 | 120.21 (9) | H52—C5—H53 | 113 (3) |
N2—N1—C2 | 119.30 (11) | N2—C6—O6 | 110.44 (10) |
N1—N2—C6 | 118.58 (10) | N2—C6—O5 | 123.06 (12) |
N1—N2—H1 | 117.0 (11) | O6—C6—O5 | 126.49 (12) |
C6—N2—H1 | 123.3 (11) | O6—C7—C8 | 109.42 (12) |
S1—C1—H11 | 105.7 (11) | O6—C7—C9 | 105.35 (13) |
S1—C1—H12 | 109.4 (12) | C8—C7—C9 | 113.84 (16) |
H11—C1—H12 | 110.3 (15) | O6—C7—H71 | 106.1 (11) |
S1—C1—H13 | 109.6 (11) | C8—C7—H71 | 111.3 (11) |
H11—C1—H13 | 112.0 (15) | C9—C7—H71 | 110.3 (10) |
H12—C1—H13 | 109.7 (16) | C7—C8—H81 | 109.6 (13) |
N1—C2—O4 | 110.13 (11) | C7—C8—H82 | 112.7 (13) |
N1—C2—O3 | 122.58 (12) | H81—C8—H82 | 106.6 (18) |
O4—C2—O3 | 127.30 (13) | C7—C8—H83 | 108.6 (14) |
O4—C3—C4 | 109.95 (16) | H81—C8—H83 | 111.4 (19) |
O4—C3—C5 | 105.09 (17) | H82—C8—H83 | 107.9 (18) |
C4—C3—C5 | 114.8 (2) | C7—C9—H91 | 110.0 (13) |
O4—C3—H31 | 106.4 (12) | C7—C9—H92 | 110.1 (14) |
C4—C3—H31 | 108.0 (13) | H91—C9—H92 | 103.7 (18) |
C5—C3—H31 | 112.2 (13) | C7—C9—H93 | 110.3 (13) |
C3—C4—H41 | 107.7 (12) | H91—C9—H93 | 110.0 (18) |
C3—C4—H42 | 103.7 (12) | H92—C9—H93 | 113 (2) |
| | | |
S1—N1—N2—C6 | 90.2 (1) | O5—C6—N2—N1 | −5.5 (2) |
S1—N1—C2—O3 | 3.2 (2) | O6—C6—N2—N1 | 175.5 (1) |
S1—N1—C2—O4 | −177.4 (1) | N1—C2—O4—C3 | 175.4 (1) |
O1—S1—N1—N2 | 145.3 (1) | N2—N1—S1—C1 | −98.2 (1) |
O1—S1—N1—C2 | −55.4 (1) | N2—C6—O6—C7 | −176.2 (1) |
O2—S1—N1—N2 | 17.6 (1) | C1—S1—N1—C2 | 61.1 (1) |
O2—S1—N1—C2 | 176.9 (1) | C2—O4—C3—C4 | 85.4 (2) |
O3—C2—O4—C3 | −5.2 (3) | C2—O4—C3—C5 | −150.6 (2) |
O3—C2—N1—N2 | 162.0 (1) | C2—N1—N2—C6 | −69.3 (2) |
O4—C2—N1—N2 | −18.5 (2) | C6—O6—C7—C8 | 79.5 (2) |
O5—C6—O6—C7 | 4.8 (2) | C6—O6—C7—C9 | −157.7 (1) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, y−1/2, −z+1/2; (iii) x, −y+1/2, z−1/2; (iv) x−1, −y+1/2, z−1/2; (v) −x, y−1/2, −z+1/2; (vi) x, −y+1/2, z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1···O5iii | 0.83 (2) | 1.99 (2) | 2.806 (2) | 168 (2) |
Symmetry code: (iii) x, −y+1/2, z−1/2. |