Diisopropyl 1-(methyl­sulfon­yl)hydrazine-1,2-dicarboxyl­ate

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.

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3	Plate, colourless
Z = 4	0.43 × 0.40 × 0.08 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.089	w = [1-(Fo-Fc)^2/36σ^2(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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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···C1^i	3.336 (2)	O3···C1^i	3.318 (2)
O1···C8^ii	3.461 (3)	O5···N2^vi	2.806 (2)
O1···C8^iii	3.594 (2)	O5···N1^vi	3.499 (2)
O2···C5^iv	3.525 (3)	O6···C1^iii	3.479 (2)
O2···C9^v	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)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O5^iii	0.83 (2)	1.99 (2)	2.806 (2)	168 (2)

Symmetry code: (iii) x, −y+1/2, z−1/2.