tert-Butyl N-[N,N-bis-(2-chloro-ethyl)sulfamo-yl]-N-(2-chloro-ethyl)carbamate.

The title compound, C(11)H(21)Cl(3)N(2)O(4)S, was produced as part of a development programme of a new synthetic route to chloro-ethyl-nitro-sosulfamides (CENS) with three chloro-ethyl moieties. These compounds possess structural features that confer potential biological activity and act as alkyl-ating agents. The packing is governed by four weak C-H⋯O inter-actions, forming an infinite three-dimensional network.

Related literature

For the potential biological activity, pharmaceutical utility and cytotoxic activity of chloro­ethyl­nitro­sosulfamides, see: Abdaoui et al. (1996 ▶, 2000 ▶); Dokhane et al. (2002 ▶); Galešić et al. (1987 ▶); Gnewuch & Sosnovsky (1997 ▶); Ishiguro et al. (2006 ▶); Jonnalagadda et al. (2007 ▶); Passagne et al. (2003 ▶); Seridi et al. (2006 ▶); Skinner & Scharts (1972 ▶); Voutsinas et al. (1993 ▶); Winum et al. (2003 ▶). For the synthetic procedure, see: Mitsunobu (1981 ▶).

Experimental

Crystal data

C11H21Cl3N2O4S

M = 383.71

Monoclinic,

a = 9.6132 (5) Å

b = 17.1282 (9) Å

c = 10.6763 (5) Å

β = 93.868 (3)°

V = 1753.92 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.66 mm−1

T = 100 K

0.15 × 0.12 × 0.1 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.862, T max = 0.937

17775 measured reflections

3982 independent reflections

3662 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.068

S = 1.03

3982 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.39 e Å−3

Data collection: SMART (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809038185/dn2489sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038185/dn2489Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H21Cl3N2O4S	F(000) = 800
Mr = 383.71	Dx = 1.453 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9788 reflections
a = 9.6132 (5) Å	θ = 2.4–27.4°
b = 17.1282 (9) Å	µ = 0.66 mm−1
c = 10.6763 (5) Å	T = 100 K
β = 93.868 (3)°	Prism, colourless
V = 1753.92 (15) Å3	0.15 × 0.12 × 0.1 mm
Z = 4

Bruker APEXII diffractometer	3982 independent reflections
Radiation source: APEXII, Bruker-AXS	3662 reflections with I > 2σ(I)
graphite	Rint = 0.037
CCD rotation images, thick slices scans	θmax = 27.4°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −12→11
Tmin = 0.862, Tmax = 0.937	k = −22→21
17775 measured reflections	l = −13→13

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0272P)2 + 0.8873P] where P = (Fo2 + 2Fc2)/3
3982 reflections	(Δ/σ)max = 0.001
193 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C1	0.30088 (13)	−0.00247 (8)	0.74767 (12)	0.0142 (3)
H1A	0.3977	−0.0155	0.7375	0.017*
H1B	0.2483	−0.0120	0.6684	0.017*
C2	0.24504 (14)	−0.05402 (8)	0.84875 (13)	0.0166 (3)
H2A	0.1511	−0.0381	0.8649	0.020*
H2B	0.3033	−0.0489	0.9261	0.020*
C3	0.16945 (13)	0.12486 (8)	0.74993 (12)	0.0141 (3)
C4	−0.07329 (14)	0.11154 (9)	0.66503 (14)	0.0212 (3)
C5	−0.15279 (16)	0.03860 (10)	0.62057 (17)	0.0332 (4)
H5A	−0.1090	0.0162	0.5508	0.050*
H5B	−0.2473	0.0523	0.5950	0.050*
H5C	−0.1521	0.0014	0.6878	0.050*
C6	−0.05995 (16)	0.16890 (10)	0.55745 (15)	0.0281 (3)
H6A	−0.0128	0.2151	0.5885	0.042*
H6B	−0.1511	0.1825	0.5220	0.042*
H6C	−0.0075	0.1452	0.4941	0.042*
C7	−0.13690 (15)	0.14725 (10)	0.77813 (15)	0.0285 (3)
H7A	−0.1375	0.1092	0.8442	0.043*
H7B	−0.2307	0.1635	0.7550	0.043*
H7C	−0.0827	0.1916	0.8068	0.043*
C8	0.38802 (13)	0.13068 (8)	1.08849 (12)	0.0150 (3)
H8A	0.4597	0.1523	1.1468	0.018*
H8B	0.4115	0.0765	1.0741	0.018*
C9	0.24946 (14)	0.13378 (8)	1.14857 (13)	0.0184 (3)
H91	0.2239	0.1879	1.1609	0.022*
H92	0.2594	0.1090	1.2304	0.022*
C10	0.36795 (13)	0.25857 (8)	0.96777 (12)	0.0139 (3)
H10A	0.3144	0.2731	1.0379	0.017*
H10B	0.3146	0.2733	0.8910	0.017*
C11	0.50586 (14)	0.30294 (8)	0.97652 (12)	0.0158 (3)
H11A	0.5593	0.2904	0.9053	0.019*
H11B	0.5605	0.2888	1.0528	0.019*
Cl1	0.24477 (4)	−0.15386 (2)	0.79617 (4)	0.02567 (9)
Cl2	0.11302 (3)	0.08604 (2)	1.05440 (3)	0.02616 (10)
Cl3	0.46514 (4)	0.40555 (2)	0.97723 (3)	0.02271 (9)
N1	0.29004 (10)	0.08109 (6)	0.78128 (10)	0.0123 (2)
N2	0.38924 (11)	0.17329 (6)	0.96878 (9)	0.0121 (2)
O1	0.52796 (9)	0.06756 (6)	0.87615 (9)	0.01627 (19)
O2	0.46793 (9)	0.18884 (6)	0.75688 (8)	0.0161 (2)
O3	0.16339 (9)	0.19465 (6)	0.76460 (9)	0.0177 (2)
O4	0.06748 (9)	0.07794 (6)	0.70365 (9)	0.0181 (2)
S1	0.43157 (3)	0.129314 (19)	0.84310 (3)	0.01123 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0159 (6)	0.0112 (7)	0.0153 (6)	0.0002 (5)	−0.0004 (4)	−0.0037 (5)
C2	0.0169 (6)	0.0110 (7)	0.0219 (7)	−0.0006 (5)	0.0011 (5)	−0.0016 (5)
C3	0.0131 (6)	0.0153 (7)	0.0136 (6)	−0.0015 (5)	−0.0015 (4)	0.0027 (5)
C4	0.0122 (6)	0.0221 (8)	0.0283 (7)	−0.0004 (5)	−0.0076 (5)	0.0057 (6)
C5	0.0238 (8)	0.0296 (9)	0.0438 (10)	−0.0088 (6)	−0.0159 (7)	0.0055 (7)
C6	0.0227 (7)	0.0311 (9)	0.0292 (8)	−0.0003 (6)	−0.0074 (6)	0.0102 (7)
C7	0.0161 (7)	0.0343 (9)	0.0347 (9)	0.0020 (6)	0.0001 (6)	0.0067 (7)
C8	0.0183 (6)	0.0143 (7)	0.0120 (6)	−0.0011 (5)	−0.0008 (5)	0.0028 (5)
C9	0.0248 (7)	0.0161 (7)	0.0149 (6)	−0.0041 (5)	0.0052 (5)	−0.0016 (5)
C10	0.0165 (6)	0.0094 (6)	0.0158 (6)	−0.0009 (5)	0.0008 (5)	0.0000 (5)
C11	0.0197 (6)	0.0114 (7)	0.0166 (6)	−0.0031 (5)	0.0027 (5)	−0.0008 (5)
Cl1	0.02584 (18)	0.01139 (18)	0.0396 (2)	−0.00249 (13)	0.00118 (14)	−0.00252 (14)
Cl2	0.01773 (16)	0.0387 (2)	0.02252 (18)	−0.00801 (14)	0.00518 (12)	−0.00232 (15)
Cl3	0.03418 (19)	0.01075 (17)	0.02329 (18)	−0.00579 (13)	0.00268 (13)	0.00063 (12)
N1	0.0116 (5)	0.0097 (6)	0.0153 (5)	−0.0015 (4)	−0.0014 (4)	−0.0013 (4)
N2	0.0158 (5)	0.0093 (5)	0.0112 (5)	−0.0010 (4)	0.0014 (4)	−0.0002 (4)
O1	0.0130 (4)	0.0164 (5)	0.0190 (5)	0.0027 (4)	−0.0014 (3)	−0.0026 (4)
O2	0.0182 (4)	0.0162 (5)	0.0139 (4)	−0.0048 (4)	0.0031 (3)	0.0001 (4)
O3	0.0164 (4)	0.0112 (5)	0.0247 (5)	0.0001 (3)	−0.0037 (4)	0.0019 (4)
O4	0.0138 (4)	0.0142 (5)	0.0251 (5)	−0.0013 (4)	−0.0071 (4)	0.0017 (4)
S1	0.01039 (14)	0.01148 (17)	0.01178 (15)	−0.00120 (11)	0.00045 (10)	−0.00080 (11)

C1—N1	1.4809 (17)	C7—H7B	0.9600
C1—C2	1.5201 (18)	C7—H7C	0.9600
C1—H1A	0.9700	C8—N2	1.4725 (16)
C1—H1B	0.9700	C8—C9	1.5178 (18)
C2—Cl1	1.7997 (14)	C8—H8A	0.9700
C2—H2A	0.9700	C8—H8B	0.9700
C2—H2B	0.9700	C9—Cl2	1.7950 (14)
C3—O3	1.2074 (17)	C9—H91	0.9700
C3—O4	1.3364 (15)	C9—H92	0.9700
C3—N1	1.4020 (16)	C10—N2	1.4749 (17)
C4—O4	1.5024 (15)	C10—C11	1.5255 (17)
C4—C7	1.519 (2)	C10—H10A	0.9700
C4—C6	1.523 (2)	C10—H10B	0.9700
C4—C5	1.524 (2)	C11—Cl3	1.8007 (14)
C5—H5A	0.9600	C11—H11A	0.9700
C5—H5B	0.9600	C11—H11B	0.9700
C5—H5C	0.9600	N1—S1	1.6875 (10)
C6—H6A	0.9600	N2—S1	1.6147 (11)
C6—H6B	0.9600	O1—S1	1.4345 (10)
C6—H6C	0.9600	O2—S1	1.4326 (10)
C7—H7A	0.9600
N1—C1—C2	110.82 (10)	H7B—C7—H7C	109.5
N1—C1—H1A	109.5	N2—C8—C9	114.08 (11)
C2—C1—H1A	109.5	N2—C8—H8A	108.7
N1—C1—H1B	109.5	C9—C8—H8A	108.7
C2—C1—H1B	109.5	N2—C8—H8B	108.7
H1A—C1—H1B	108.1	C9—C8—H8B	108.7
C1—C2—Cl1	108.88 (9)	H8A—C8—H8B	107.6
C1—C2—H2A	109.9	C8—C9—Cl2	112.10 (9)
Cl1—C2—H2A	109.9	C8—C9—H91	109.2
C1—C2—H2B	109.9	Cl2—C9—H91	109.2
Cl1—C2—H2B	109.9	C8—C9—H92	109.2
H2A—C2—H2B	108.3	Cl2—C9—H92	109.2
O3—C3—O4	127.07 (12)	H91—C9—H92	107.9
O3—C3—N1	123.01 (11)	N2—C10—C11	111.92 (10)
O4—C3—N1	109.92 (11)	N2—C10—H10A	109.2
O4—C4—C7	109.86 (11)	C11—C10—H10A	109.2
O4—C4—C6	109.51 (11)	N2—C10—H10B	109.2
C7—C4—C6	113.49 (13)	C11—C10—H10B	109.2
O4—C4—C5	101.24 (11)	H10A—C10—H10B	107.9
C7—C4—C5	110.95 (13)	C10—C11—Cl3	107.35 (9)
C6—C4—C5	111.09 (13)	C10—C11—H11A	110.2
C4—C5—H5A	109.5	Cl3—C11—H11A	110.2
C4—C5—H5B	109.5	C10—C11—H11B	110.2
H5A—C5—H5B	109.5	Cl3—C11—H11B	110.2
C4—C5—H5C	109.5	H11A—C11—H11B	108.5
H5A—C5—H5C	109.5	C3—N1—C1	121.97 (10)
H5B—C5—H5C	109.5	C3—N1—S1	117.61 (9)
C4—C6—H6A	109.5	C1—N1—S1	119.98 (8)
C4—C6—H6B	109.5	C8—N2—C10	119.21 (10)
H6A—C6—H6B	109.5	C8—N2—S1	120.48 (9)
C4—C6—H6C	109.5	C10—N2—S1	119.90 (8)
H6A—C6—H6C	109.5	C3—O4—C4	119.72 (11)
H6B—C6—H6C	109.5	O2—S1—O1	120.08 (6)
C4—C7—H7A	109.5	O2—S1—N2	106.74 (6)
C4—C7—H7B	109.5	O1—S1—N2	109.53 (6)
H7A—C7—H7B	109.5	O2—S1—N1	108.80 (5)
C4—C7—H7C	109.5	O1—S1—N1	103.05 (5)
H7A—C7—H7C	109.5	N2—S1—N1	108.16 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O1i	0.97	2.59	3.5465 (16)	167
C8—H8B···O1i	0.97	2.58	3.5047 (17)	159
C9—H91···O3ii	0.97	2.39	3.3156 (17)	160
C11—H11B···O2ii	0.97	2.44	3.0428 (16)	120

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯O1i	0.97	2.59	3.5465 (16)	167
C8—H8B⋯O1i	0.97	2.58	3.5047 (17)	159
C9—H91⋯O3ii	0.97	2.39	3.3156 (17)	160
C11—H11B⋯O2ii	0.97	2.44	3.0428 (16)	120

Symmetry codes: (i) ; (ii) .