(3RS)-S-[1-(3-Chloro-phen-yl)-2-oxopyr-rolidin-3-yl]-N,N'-dimethyl-thio-uronium bromide.

The title mol-ecule, C(13)H(17)ClN(3)OS(+)·Br(-), consists of benzene and pyrrolidine rings and an S-C(NHCH(3))(2) group. The central C-N bond lengths in the S-C(NHCH(3))(2) fragment indicate partial double-bond character. Mol-ecules are inter-connected into chains by N-H⋯Br hydrogen bonds and the chains are linked into pairs by weak C-H⋯Br hydrogen bonds.

Related literature

For the reactivity of the title compound, see: Hanusek et al. (2004 ▶); Sedlák et al. (2002 ▶, 2003 ▶). For a related structure, see: Hanusek et al. (2009 ▶).

Experimental

Crystal data

C13H17ClN3OS+·n class="Chemical">Br−

M = 378.72

Monoclinic,

a = 14.9409 (9) Å

b = 7.7050 (5) Å

c = 13.9141 (15) Å

β = 100.758 (7)°

V = 1573.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 2.91 mm−1

T = 150 (2) K

0.41 × 0.40 × 0.22 mm

Data collection

Bruker–n class="Chemical">Nonius KappaCCD diffractometer

Absorption correction: gaussian integration (Coppens, 1970 ▶) T min = 0.401, T max = 0.658

11628 measured reflections

3455 independent reflections

2671 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.114

S = 1.22

3455 reflections

189 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.74 e Å−3

Δρmin = −0.82 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶) and DENZO (Otwinowski and Minor, 1997 ▶); cell refinement: COLLECT and DENZO; data reduction: COLLECT and DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809002153/fb2123sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002153/fb2123Isup2.hkl

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

C13H17ClN3OS+·Br−	F(000) = 768
Mr = 378.72	Dx = 1.599 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11663 reflections
a = 14.9409 (9) Å	θ = 1–27.5°
b = 7.7050 (5) Å	µ = 2.91 mm−1
c = 13.9141 (15) Å	T = 150 K
β = 100.758 (7)°	Block, colourless
V = 1573.6 (2) Å3	0.41 × 0.40 × 0.22 mm
Z = 4

Bruker–Nonius KappaCCD diffractometer	3455 independent reflections
Radiation source: fine-focus sealed tube	2671 reflections with I > 2σ(I)
graphite	Rint = 0.060
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 2.8°
φ and ω scans	h = −19→16
Absorption correction: gaussian integration (Coppens, 1970)	k = −8→9
Tmin = 0.401, Tmax = 0.658	l = −17→18
11628 measured reflections

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)] = 0.048	Hydrogen site location: difference Fourier map
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.22	w = 1/[σ2(Fo2) + (0.0325P)2 + 3.4975P] where P = (Fo2 + 2Fc2)/3
3455 reflections	(Δ/σ)max < 0.001
189 parameters	Δρmax = 0.74 e Å−3
0 restraints	Δρmin = −0.82 e Å−3
60 constraints

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 > 2sigma(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
Br1	0.08338 (3)	0.66896 (5)	0.14195 (3)	0.02613 (13)
S1	0.16212 (7)	0.32645 (15)	0.36335 (7)	0.0259 (2)
Cl1	0.62396 (8)	−0.16871 (15)	0.42796 (8)	0.0356 (3)
N3	0.1148 (2)	0.0146 (5)	0.2861 (3)	0.0225 (7)
H3	0.095 (3)	−0.053 (7)	0.245 (3)	0.027*
O1	0.3250 (2)	0.1248 (4)	0.3000 (2)	0.0340 (7)
C1	0.3345 (3)	0.2769 (5)	0.3210 (3)	0.0219 (8)
N1	0.4148 (2)	0.3623 (4)	0.3524 (2)	0.0221 (7)
N2	0.0914 (2)	0.2457 (5)	0.1804 (3)	0.0244 (7)
H2	0.094 (3)	0.350 (7)	0.178 (4)	0.029*
C11	0.1189 (2)	0.1804 (5)	0.2677 (3)	0.0207 (8)
C6	0.5171 (3)	0.1131 (5)	0.3865 (3)	0.0211 (8)
H6	0.4680	0.0399	0.3948	0.025*
C7	0.6049 (3)	0.0507 (5)	0.3989 (3)	0.0246 (9)
C10	0.5754 (3)	0.3920 (6)	0.3476 (3)	0.0261 (9)
H10	0.5652	0.5102	0.3293	0.031*
C13	0.1428 (3)	−0.0649 (6)	0.3822 (3)	0.0338 (11)
H13A	0.2066	−0.0358	0.4080	0.051*
H13B	0.1362	−0.1912	0.3763	0.051*
H13C	0.1044	−0.0211	0.4267	0.051*
C9	0.6624 (3)	0.3230 (6)	0.3608 (3)	0.0278 (9)
H9	0.7118	0.3945	0.3513	0.033*
C4	0.2588 (3)	0.4101 (6)	0.3153 (3)	0.0244 (9)
H4	0.2380	0.4459	0.2456	0.029*
C2	0.4027 (3)	0.5482 (5)	0.3675 (3)	0.0253 (9)
H2A	0.4168	0.6166	0.3119	0.030*
H2B	0.4421	0.5883	0.4286	0.030*
C5	0.5029 (3)	0.2873 (5)	0.3613 (3)	0.0214 (8)
C12	0.0567 (3)	0.1404 (6)	0.0946 (3)	0.0341 (11)
H12A	0.1048	0.0626	0.0814	0.051*
H12B	0.0372	0.2163	0.0381	0.051*
H12C	0.0048	0.0716	0.1067	0.051*
C3	0.3028 (3)	0.5640 (6)	0.3739 (4)	0.0333 (10)
H3A	0.2770	0.6748	0.3451	0.040*
H3B	0.2943	0.5575	0.4427	0.040*
C8	0.6784 (3)	0.1510 (6)	0.3878 (3)	0.0269 (9)
H8	0.7382	0.1040	0.3983	0.032*

	U11	U22	U33	U12	U13	U23
Br1	0.0262 (2)	0.0177 (2)	0.0348 (2)	0.00117 (17)	0.00640 (16)	0.00120 (18)
S1	0.0265 (5)	0.0298 (6)	0.0225 (5)	0.0025 (4)	0.0072 (4)	−0.0046 (4)
Cl1	0.0406 (6)	0.0266 (6)	0.0408 (6)	0.0100 (5)	0.0110 (5)	0.0056 (5)
N3	0.0272 (18)	0.0174 (17)	0.0243 (17)	0.0039 (14)	0.0076 (14)	0.0040 (14)
O1	0.0263 (16)	0.0280 (17)	0.0495 (19)	−0.0037 (12)	0.0118 (14)	−0.0165 (15)
C1	0.020 (2)	0.024 (2)	0.0221 (19)	0.0002 (16)	0.0055 (15)	−0.0043 (17)
N1	0.0251 (17)	0.0195 (18)	0.0217 (16)	−0.0013 (14)	0.0049 (13)	−0.0019 (14)
N2	0.0302 (19)	0.0190 (18)	0.0231 (17)	−0.0002 (15)	0.0030 (14)	0.0019 (16)
C11	0.0189 (18)	0.023 (2)	0.0203 (18)	0.0039 (16)	0.0055 (14)	−0.0034 (17)
C6	0.025 (2)	0.0185 (19)	0.0207 (19)	−0.0008 (15)	0.0072 (15)	−0.0007 (16)
C7	0.032 (2)	0.022 (2)	0.0211 (19)	0.0008 (17)	0.0084 (17)	−0.0003 (17)
C10	0.028 (2)	0.025 (2)	0.025 (2)	−0.0053 (17)	0.0041 (16)	0.0003 (18)
C13	0.040 (3)	0.031 (3)	0.031 (2)	0.013 (2)	0.011 (2)	0.014 (2)
C9	0.027 (2)	0.032 (2)	0.024 (2)	−0.0101 (19)	0.0045 (16)	−0.0005 (19)
C4	0.024 (2)	0.026 (2)	0.023 (2)	−0.0019 (17)	0.0037 (16)	−0.0023 (18)
C2	0.030 (2)	0.018 (2)	0.025 (2)	0.0010 (16)	−0.0010 (17)	0.0004 (17)
C5	0.023 (2)	0.024 (2)	0.0176 (18)	−0.0012 (15)	0.0054 (15)	−0.0028 (16)
C12	0.048 (3)	0.028 (3)	0.023 (2)	−0.003 (2)	−0.0016 (19)	−0.0004 (19)
C3	0.031 (2)	0.027 (2)	0.041 (3)	0.0028 (18)	0.0038 (19)	−0.012 (2)
C8	0.024 (2)	0.038 (3)	0.0196 (19)	0.0029 (18)	0.0055 (15)	−0.0030 (19)

S1—C11	1.770 (4)	C10—C5	1.391 (6)
S1—C4	1.819 (4)	C10—H10	0.9500
Cl1—C7	1.749 (4)	C13—H13A	0.9800
N3—C11	1.307 (5)	C13—H13B	0.9800
N3—C13	1.459 (5)	C13—H13C	0.9800
N3—H3	0.80 (5)	C9—C8	1.385 (6)
O1—C1	1.210 (5)	C9—H9	0.9500
C1—N1	1.367 (5)	C4—C3	1.518 (6)
C1—C4	1.518 (6)	C4—H4	1.0000
N1—C5	1.421 (5)	C2—C3	1.516 (6)
N1—C2	1.464 (5)	C2—H2A	0.9900
N2—C11	1.309 (5)	C2—H2B	0.9900
N2—C12	1.456 (5)	C12—H12A	0.9800
N2—H2	0.81 (5)	C12—H12B	0.9800
C6—C7	1.377 (6)	C12—H12C	0.9800
C6—C5	1.394 (6)	C3—H3A	0.9900
C6—H6	0.9500	C3—H3B	0.9900
C7—C8	1.375 (6)	C8—H8	0.9500
C10—C9	1.385 (6)
C11—S1—C4	98.74 (18)	C10—C9—H9	119.6
C11—N3—C13	125.0 (4)	C8—C9—H9	119.6
C11—N3—H3	122 (4)	C3—C4—C1	104.8 (3)
C13—N3—H3	113 (4)	C3—C4—S1	111.9 (3)
O1—C1—N1	126.8 (4)	C1—C4—S1	112.1 (3)
O1—C1—C4	126.1 (4)	C3—C4—H4	109.3
N1—C1—C4	107.0 (3)	C1—C4—H4	109.3
C1—N1—C5	125.1 (3)	S1—C4—H4	109.3
C1—N1—C2	113.0 (3)	N1—C2—C3	103.7 (3)
C5—N1—C2	121.5 (3)	N1—C2—H2A	111.0
C11—N2—C12	123.3 (4)	C3—C2—H2A	111.0
C11—N2—H2	114 (4)	N1—C2—H2B	111.0
C12—N2—H2	122 (4)	C3—C2—H2B	111.0
N3—C11—N2	122.6 (4)	H2A—C2—H2B	109.0
N3—C11—S1	119.9 (3)	C10—C5—C6	120.4 (4)
N2—C11—S1	117.4 (3)	C10—C5—N1	118.9 (4)
C7—C6—C5	117.7 (4)	C6—C5—N1	120.6 (4)
C7—C6—H6	121.1	N2—C12—H12A	109.5
C5—C6—H6	121.1	N2—C12—H12B	109.5
C8—C7—C6	123.4 (4)	H12A—C12—H12B	109.5
C8—C7—Cl1	118.1 (3)	N2—C12—H12C	109.5
C6—C7—Cl1	118.5 (3)	H12A—C12—H12C	109.5
C9—C10—C5	119.6 (4)	H12B—C12—H12C	109.5
C9—C10—H10	120.2	C2—C3—C4	103.8 (3)
C5—C10—H10	120.2	C2—C3—H3A	111.0
N3—C13—H13A	109.5	C4—C3—H3A	111.0
N3—C13—H13B	109.5	C2—C3—H3B	111.0
H13A—C13—H13B	109.5	C4—C3—H3B	111.0
N3—C13—H13C	109.5	H3A—C3—H3B	109.0
H13A—C13—H13C	109.5	C7—C8—C9	117.9 (4)
H13B—C13—H13C	109.5	C7—C8—H8	121.1
C10—C9—C8	120.9 (4)	C9—C8—H8	121.1

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···Br1i	0.80 (5)	2.56 (5)	3.314 (4)	159 (5)
N2—H2···Br1	0.81 (5)	2.51 (5)	3.303 (4)	170 (5)
C6—H6···O1	0.95	2.38	2.899 (5)	114
C8—H8···Br1ii	0.95	2.87	3.662 (5)	142
C2—H2A···Cg1iii	0.99	2.69	3.628 (4)	159

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C5–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯Br1i	0.80 (5)	2.56 (5)	3.314 (4)	159 (5)
N2—H2⋯Br1	0.81 (5)	2.51 (5)	3.303 (4)	170 (5)
C6—H6⋯O1	0.95	2.38	2.899 (5)	114
C8—H8⋯Br1ii	0.95	2.87	3.662 (5)	142
C2—H2A⋯Cg1iii	0.99	2.69	3.628 (4)	159

Symmetry codes: (i) ; (ii) ; (iii) .