(3RS)-S-[1-(3-Chloro­phen­yl)-2-oxopyr­rolidin-3-yl]-N,N′-dimethyl­thio­uronium bromide

Hanusek, J.; Sedlák, M.; Drabina, P.; Ružička, A.

doi:10.1107/S1600536809002153

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o413

doi:10.1107/S1600536809002153

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(3RS)-S-[1-(3-Chlorophenyl)-2-oxopyrrolidin-3-yl]-N,N′-dimethylthiouronium bromide

Jiří Hanusek,^a ^* Miloš Sedlák,^a Pavel Drabina ^a and Aleš Ružička ^b

^aInstitute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, nám. Čs. legií 565, Pardubice 532 10, Czech Republic, and ^bDepartment of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, nám. Čs. legií 565, Pardubice 532 10, Czech Republic
^*Correspondence e-mail: jiri.hanusek@upce.cz

(Received 16 October 2008; accepted 16 January 2009; online 28 January 2009)

The title molecule, C₁₃H₁₇ClN₃OS⁺·Br⁻, consists of benzene and pyrrolidine rings and an S–C(NHCH₃)₂ group. The central C—N bond lengths in the S–C(NHCH₃)₂ fragment indicate partial double-bond character. Molecules are interconnected 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⁺·Br⁻
M_r = 378.72
Monoclinic, P 2₁ /c
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–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[F² > 2σ(F²)] = 0.048
wR(F²) = 0.114
S = 1.22
3455 reflections
189 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.74 e Å⁻³
Δρ_min = −0.82 e Å⁻³

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) x, y-1, z; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

In our previous papers we have discussed the reactivity of the title structure (Sedlák et al., 2002, 2003; Hanusek et al., 2004). In continuation of the above mentioned studies, the related crystal structures of the title compound (Scheme 1, Figs. 1 and 2) as well as of the non-methylated analogue (Hanusek et al., 2009) have been determined and the influence of the N-methyl substituents on the crystal structure has been examined.

The respective important distances for the title compound and its non-methylated analogue are 1.770 (4) and 1.749 (4) Å for S1–C11; (1.307 (5), 1.309 (5) Å) and (1.312 (5), 1.296 (5) Å) for C11–N2 and C11–N3. The respective twist angles about the N1–C5 bonds in the title compound and its non-methylated analogue are 28.8 (2) and 7.8 (1)°.

The interplanar angles between the S—C(NHR)₂ group and the heterocyclic rings are almost the same in the title compound and its non-methylated analogue (71.3 (1) and 66.7 (1)°). In the S–C(NHCH₃)₂ fragment of the title compound, the C-N bond-lengths of N2-C11 and N3-C11 (1.309 (5), 1.307 (5) Å, respectively) indicate a partly double bond character.

All the isothiouronium cations that have been studied in the solid state take part in the hydrogen bonding with different anions. (These anions comprise Cl^- as well as complex organic anions.) Also in the title compound and its non-methylated analogue such interactions are present. In the title structure, there is a motif N2–H2···Br1···H1–N1 that links the molecules into the infinite chains parallel to the b axis (Fig. 2, Tab. 1). Moreover, the pairs of these chains are interconnected by additional C–H···Br contacts to give columns parallel to the b axis. These pairs of the chains are linked by the virtue of two-fold screw axes. There is also a weak C–H···π-electron interaction with π-electrons of the chlorophenyl ring (Tab. 1).

Related literature top

For reactivity

of the title compound, see: Hanusek et al. (2004); Sedlák et al. (2002, 2003). For a related structure, see: Hanusek et al. (2009). Cg1 is the centroid of the C5–C10 ring.

Experimental top

The title compound was synthesized according to Hanusek et al. (2004) from saturated acetone solutions of the racemic 3-bromo-1-(3-chlorophenyl)pyrrolidin-2-one and N,N'-dimethylthiourea. Single crystals (blocks) suitable for analysis were grown directly from the reaction mixture. Their average size was 0.3×0.3×0.2 mm

Computing details top

Data collection: COLLECT (Hooft, 1998) and DENZO (Otwinowski and Minor, 1997); cell refinement: COLLECT (Hooft, 1998) and DENZO (Otwinowski and Minor, 1997); data reduction: COLLECT (Hooft, 1998) and DENZO (Otwinowski and Minor, 1997); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. View of the title molecule. The displacement ellipsoids are shown at the 50% probability level. The hydrogens are shown as circles with arbitrary radius.
	Fig. 2. Motif showing the hydrogen bonding in the title structure. Symmetry code for Br1 b: x, 1-y, z.

(3RS)-S-[1-(3-Chlorophenyl)-2-oxopyrrolidin-3-yl]- N,N'-dimethylthiouronium bromide top

Crystal data top

C₁₃H₁₇ClN₃OS⁺·Br⁻	F(000) = 768
M_r = 378.72	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0325P)² + 3.4975P] where P = (F_o² + 2F_c²)/3
3455 reflections	(Δ/σ)_max < 0.001
189 parameters	Δρ_max = 0.74 e Å⁻³
0 restraints	Δρ_min = −0.82 e Å⁻³
60 constraints

Crystal data top

C₁₃H₁₇ClN₃OS⁺·Br⁻	V = 1573.6 (2) Å³
M_r = 378.72	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.9409 (9) Å	µ = 2.91 mm⁻¹
b = 7.7050 (5) Å	T = 150 K
c = 13.9141 (15) Å	0.41 × 0.40 × 0.22 mm
β = 100.758 (7)°

Data collection top

Bruker–Nonius KappaCCD diffractometer	3455 independent reflections
Absorption correction: gaussian integration (Coppens, 1970)	2671 reflections with I > 2σ(I)
T_min = 0.401, T_max = 0.658	R_int = 0.060
11628 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.22	Δρ_max = 0.74 e Å⁻³
3455 reflections	Δρ_min = −0.82 e Å⁻³
189 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) x, y−1, z; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₇ClN₃OS⁺·Br⁻
M_r	378.72
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	14.9409 (9), 7.7050 (5), 13.9141 (15)
β (°)	100.758 (7)
V (Å³)	1573.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.91
Crystal size (mm)	0.41 × 0.40 × 0.22

Data collection
Diffractometer	Bruker–Nonius KappaCCD diffractometer
Absorption correction	Gaussian integration (Coppens, 1970)
T_min, T_max	0.401, 0.658
No. of measured, independent and observed [I > 2σ(I)] reflections	11628, 3455, 2671
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.114, 1.22
No. of reflections	3455
No. of parameters	189
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.74, −0.82

Computer programs: COLLECT (Hooft, 1998) and DENZO (Otwinowski and Minor, 1997), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

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) x, y−1, z; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+1, y+1/2, −z+1/2.

Acknowledgements

The authors thank the Ministry of Education, Youth and Sports of the Czech Republic for financial support of this work within the framework of research project MSM 0021627501.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
Coppens, P. (1970). Crystallographic Computing, edited by F. R. Ahmed, S. R. Hall & C. P. Huber, pp. 255–270. Copenhagen: Munksgaard. Google Scholar
Hanusek, J., Hejtmánková, L., Štěrba, V. & Sedlák, M. (2004). Org. Biomol. Chem. 2, 1756–1763. Web of Science CrossRef PubMed CAS Google Scholar
Hanusek, J., Sedlák, M., Drabina, P. & Ružička, A. (2009). Acta Cryst. E65, o411–o412. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hooft, R. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sedlák, M., Hanusek, J., Hejtmánková, L. & Kašparová, P. (2003). Org. Biomol. Chem. 1, 1204–1209. Web of Science PubMed Google Scholar
Sedlák, M., Hejtmánková, L., Hanusek, J. & Macháček, V. (2002). J. Heterocycl. Chem. 39, 1105–1107. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 2| February 2009| Page o413

doi:10.1107/S1600536809002153

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(3RS)-S-[1-(3-Chloro­phen­yl)-2-oxopyr­rolidin-3-yl]-N,N′-di­methyl­thio­uronium bromide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(3RS)-S-[1-(3-Chlorophenyl)-2-oxopyrrolidin-3-yl]-N,N′-dimethylthiouronium bromide