Crystal structure of 4-meth-oxy-N-[(pyrrolidin-1-yl)carbo-thio-yl]benzamide.

In the title compound, C13H16N2O2S, the pyrrolidine ring has a twisted conformation on the central -CH2-CH2- bond. Its mean plane is inclined to the 4-meth-oxy-benzoyl ring by 72.79 (15)°. In the crystal, mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen bonds to the same O-atom acceptor, forming chains along [001]. The chains are linked via slipped parallel π-π inter-actions [inter-centroid distance = 3.7578 (13) Å], forming undulating slabs parallel to (100).

Related literature

For thio­urea derivatives containing a carbono­thioyl R–C(=O)—N(H)—C(=S)—N functional group, where R is an alkyl or aryl group, see: Arslan et al. (2006 ▸). For copper(II) complexes of similar compounds, see: Kulcu et al. (2005 ▸); Tan et al. (2014 ▸). For the biological properties of coordination complexes of such compounds, see: Rodríguez-Fernandez et al. (2005 ▸); Cikla et al. (2010 ▸). For the crystal structures of similar compounds, see: Al-abbasi et al. (2011 ▸, 2012 ▸); Md Nasir et al. (2011 ▸); Hassan et al. (2008 ▸, 2009 ▸).

Experimental

Crystal data

C13H16N2O2S

M = 264.34

Monoclinic,

a = 11.8548 (12) Å

b = 11.4463 (11) Å

c = 9.8317 (9) Å

β = 93.124 (3)°

V = 1332.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 296 K

0.50 × 0.41 × 0.15 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▸) T min = 0.890, T max = 0.965

17732 measured reflections

2763 independent reflections

2140 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.130

S = 1.07

2763 reflections

169 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2007 ▸); cell refinement: SAINT (Bruker, 2007 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: SHELXTL (Sheldrick, 2008 ▸); software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009 ▸) and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015003813/su5083sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015003813/su5083Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015003813/su5083Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015003813/su5083fig1.tif

A view of the mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

x . DOI: 10.1107/S2056989015003813/su5083fig2.tif

A view along the x axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1 for details).

CCDC reference: 1051012

Additional supporting information: crystallographic information; 3D view; checkCIF report

C13H16N2O2S	F(000) = 560
Mr = 264.34	Dx = 1.318 Mg m−3
Monoclinic, P21/c	Melting point = 397–399 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.8548 (12) Å	θ = 3.2–26.5°
b = 11.4463 (11) Å	µ = 0.24 mm−1
c = 9.8317 (9) Å	T = 296 K
β = 93.124 (3)°	Block, pale-yellow
V = 1332.1 (2) Å3	0.50 × 0.41 × 0.15 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2763 independent reflections
Radiation source: fine-focus sealed tube	2140 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
ω scan	θmax = 26.5°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −14→14
Tmin = 0.890, Tmax = 0.965	k = −14→14
17732 measured reflections	l = −12→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.130	w = 1/[σ2(Fo2) + (0.0485P)2 + 1.055P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2763 reflections	Δρmax = 0.26 e Å−3
169 parameters	Δρmin = −0.23 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.031 (3)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
S1	0.72135 (6)	0.00137 (5)	0.03914 (6)	0.0491 (2)
O1	0.76464 (14)	0.29334 (14)	0.26290 (14)	0.0456 (4)
O2	0.93009 (16)	0.73574 (15)	−0.05668 (17)	0.0582 (5)
N1	0.71420 (15)	0.23446 (15)	0.04921 (17)	0.0345 (4)
N2	0.58223 (15)	0.13540 (14)	0.17024 (18)	0.0383 (4)
C1	0.80147 (19)	0.45074 (19)	−0.0520 (2)	0.0386 (5)
H1	0.7689	0.3985	−0.1151	0.046*
C2	0.8420 (2)	0.5562 (2)	−0.0950 (2)	0.0472 (6)
H2	0.8365	0.5748	−0.1872	0.057*
C3	0.89105 (18)	0.63501 (18)	−0.0028 (2)	0.0387 (5)
C4	0.89724 (19)	0.60796 (19)	0.1342 (2)	0.0421 (5)
H4	0.9283	0.6610	0.1973	0.051*
C5	0.85703 (19)	0.50171 (18)	0.1772 (2)	0.0383 (5)
H5	0.8623	0.4834	0.2695	0.046*
C6	0.80889 (15)	0.42189 (16)	0.08530 (18)	0.0290 (4)
C7	0.76284 (16)	0.31244 (17)	0.14072 (18)	0.0310 (4)
C8	0.66841 (17)	0.12705 (17)	0.09137 (18)	0.0320 (4)
C9	0.5215 (2)	0.2428 (2)	0.2040 (3)	0.0504 (6)
H9A	0.5074	0.2912	0.1240	0.060*
H9B	0.5640	0.2877	0.2731	0.060*
C10	0.4126 (2)	0.1985 (3)	0.2569 (4)	0.0705 (8)
H10A	0.3559	0.1871	0.1832	0.085*
H10B	0.3835	0.2521	0.3229	0.085*
C11	0.4468 (3)	0.0836 (3)	0.3227 (4)	0.0747 (9)
H11A	0.4820	0.0959	0.4129	0.090*
H11B	0.3819	0.0329	0.3299	0.090*
C12	0.5294 (2)	0.0320 (2)	0.2289 (3)	0.0469 (6)
H12A	0.5851	−0.0159	0.2787	0.056*
H12B	0.4910	−0.0150	0.1585	0.056*
C13	0.9838 (2)	0.8187 (2)	0.0323 (3)	0.0582 (7)
H13A	0.9295	0.8506	0.0911	0.087*
H13B	1.0149	0.8804	−0.0202	0.087*
H13C	1.0433	0.7813	0.0863	0.087*
H1A	0.734 (2)	0.234 (2)	−0.030 (3)	0.048 (7)*

	U11	U22	U33	U12	U13	U23
S1	0.0650 (4)	0.0340 (3)	0.0487 (4)	0.0064 (3)	0.0070 (3)	−0.0051 (2)
O1	0.0643 (10)	0.0483 (9)	0.0242 (7)	−0.0124 (8)	0.0019 (6)	0.0034 (6)
O2	0.0803 (12)	0.0404 (9)	0.0530 (10)	−0.0216 (9)	−0.0036 (9)	0.0101 (7)
N1	0.0480 (10)	0.0322 (9)	0.0237 (8)	−0.0064 (7)	0.0070 (7)	−0.0009 (7)
N2	0.0454 (10)	0.0273 (8)	0.0427 (10)	−0.0038 (7)	0.0077 (8)	0.0025 (7)
C1	0.0527 (13)	0.0360 (11)	0.0267 (10)	−0.0074 (9)	−0.0005 (9)	−0.0014 (8)
C2	0.0712 (16)	0.0421 (12)	0.0279 (10)	−0.0107 (11)	−0.0019 (10)	0.0062 (9)
C3	0.0428 (11)	0.0319 (10)	0.0415 (12)	−0.0035 (9)	0.0028 (9)	0.0038 (9)
C4	0.0489 (12)	0.0407 (12)	0.0360 (11)	−0.0089 (10)	−0.0033 (9)	−0.0059 (9)
C5	0.0473 (12)	0.0423 (12)	0.0250 (9)	−0.0068 (9)	−0.0010 (8)	−0.0006 (8)
C6	0.0293 (9)	0.0306 (9)	0.0271 (9)	0.0000 (7)	0.0030 (7)	0.0001 (7)
C7	0.0350 (10)	0.0332 (10)	0.0251 (9)	0.0007 (8)	0.0039 (7)	0.0004 (7)
C8	0.0405 (11)	0.0317 (10)	0.0236 (9)	−0.0024 (8)	−0.0011 (8)	−0.0005 (7)
C9	0.0539 (14)	0.0379 (12)	0.0614 (15)	0.0057 (10)	0.0207 (11)	0.0027 (11)
C10	0.0517 (15)	0.0604 (17)	0.101 (2)	0.0007 (13)	0.0229 (15)	−0.0096 (16)
C11	0.0720 (19)	0.0608 (17)	0.095 (2)	−0.0163 (15)	0.0387 (17)	0.0083 (16)
C12	0.0486 (13)	0.0379 (11)	0.0543 (14)	−0.0136 (10)	0.0037 (11)	0.0074 (10)
C13	0.0617 (16)	0.0372 (13)	0.0752 (18)	−0.0113 (11)	−0.0010 (13)	−0.0021 (12)

S1—C8	1.662 (2)	C5—C6	1.386 (3)
O1—C7	1.220 (2)	C5—H5	0.9300
O2—C3	1.361 (2)	C6—C7	1.482 (3)
O2—C13	1.418 (3)	C9—C10	1.505 (4)
N1—C7	1.372 (2)	C9—H9A	0.9700
N1—C8	1.415 (2)	C9—H9B	0.9700
N1—H1A	0.83 (3)	C10—C11	1.512 (4)
N2—C8	1.319 (3)	C10—H10A	0.9700
N2—C12	1.471 (3)	C10—H10B	0.9700
N2—C9	1.472 (3)	C11—C12	1.502 (4)
C1—C2	1.375 (3)	C11—H11A	0.9700
C1—C6	1.387 (3)	C11—H11B	0.9700
C1—H1	0.9300	C12—H12A	0.9700
C2—C3	1.384 (3)	C12—H12B	0.9700
C2—H2	0.9300	C13—H13A	0.9600
C3—C4	1.380 (3)	C13—H13B	0.9600
C4—C5	1.381 (3)	C13—H13C	0.9600
C4—H4	0.9300
C3—O2—C13	118.55 (19)	N2—C9—C10	103.63 (19)
C7—N1—C8	121.83 (16)	N2—C9—H9A	111.0
C7—N1—H1A	119.3 (18)	C10—C9—H9A	111.0
C8—N1—H1A	114.0 (18)	N2—C9—H9B	111.0
C8—N2—C12	122.12 (18)	C10—C9—H9B	111.0
C8—N2—C9	126.67 (17)	H9A—C9—H9B	109.0
C12—N2—C9	111.08 (17)	C9—C10—C11	103.0 (2)
C2—C1—C6	120.23 (19)	C9—C10—H10A	111.2
C2—C1—H1	119.9	C11—C10—H10A	111.2
C6—C1—H1	119.9	C9—C10—H10B	111.2
C1—C2—C3	120.82 (19)	C11—C10—H10B	111.2
C1—C2—H2	119.6	H10A—C10—H10B	109.1
C3—C2—H2	119.6	C12—C11—C10	104.4 (2)
O2—C3—C4	124.7 (2)	C12—C11—H11A	110.9
O2—C3—C2	115.90 (19)	C10—C11—H11A	110.9
C4—C3—C2	119.41 (19)	C12—C11—H11B	110.9
C3—C4—C5	119.72 (19)	C10—C11—H11B	110.9
C3—C4—H4	120.1	H11A—C11—H11B	108.9
C5—C4—H4	120.1	N2—C12—C11	103.30 (19)
C4—C5—C6	121.15 (19)	N2—C12—H12A	111.1
C4—C5—H5	119.4	C11—C12—H12A	111.1
C6—C5—H5	119.4	N2—C12—H12B	111.1
C5—C6—C1	118.65 (18)	C11—C12—H12B	111.1
C5—C6—C7	117.66 (17)	H12A—C12—H12B	109.1
C1—C6—C7	123.61 (17)	O2—C13—H13A	109.5
O1—C7—N1	120.88 (18)	O2—C13—H13B	109.5
O1—C7—C6	121.76 (18)	H13A—C13—H13B	109.5
N1—C7—C6	117.32 (16)	O2—C13—H13C	109.5
N2—C8—N1	115.53 (17)	H13A—C13—H13C	109.5
N2—C8—S1	124.18 (15)	H13B—C13—H13C	109.5
N1—C8—S1	120.28 (15)
C6—C1—C2—C3	0.2 (4)	C5—C6—C7—N1	179.28 (18)
C13—O2—C3—C4	1.7 (4)	C1—C6—C7—N1	2.5 (3)
C13—O2—C3—C2	−178.4 (2)	C12—N2—C8—N1	−176.49 (18)
C1—C2—C3—O2	178.9 (2)	C9—N2—C8—N1	8.0 (3)
C1—C2—C3—C4	−1.2 (4)	C12—N2—C8—S1	4.8 (3)
O2—C3—C4—C5	−178.5 (2)	C9—N2—C8—S1	−170.72 (18)
C2—C3—C4—C5	1.5 (3)	C7—N1—C8—N2	63.0 (3)
C3—C4—C5—C6	−0.9 (3)	C7—N1—C8—S1	−118.27 (18)
C4—C5—C6—C1	−0.1 (3)	C8—N2—C9—C10	162.6 (2)
C4—C5—C6—C7	−177.08 (19)	C12—N2—C9—C10	−13.4 (3)
C2—C1—C6—C5	0.5 (3)	N2—C9—C10—C11	31.6 (3)
C2—C1—C6—C7	177.3 (2)	C9—C10—C11—C12	−38.8 (3)
C8—N1—C7—O1	−2.6 (3)	C8—N2—C12—C11	173.3 (2)
C8—N1—C7—C6	179.56 (17)	C9—N2—C12—C11	−10.5 (3)
C5—C6—C7—O1	1.5 (3)	C10—C11—C12—N2	30.2 (3)
C1—C6—C7—O1	−175.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.83 (3)	2.11 (3)	2.927 (2)	170 (2)
C1—H1···O1i	0.93	2.50	3.350 (3)	152

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1H1AO1i	0.83(3)	2.11(3)	2.927(2)	170(2)
C1H1O1i	0.93	2.50	3.350(3)	152

Symmetry code: (i) .