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In the title compound, C12H13ClN2OS, the mol­ecule has a twisted conformation with regard to the carbonyl and thio­carbonyl groups. In the crystal structure, hydrogen-bonded pairs of mol­ecules are formed which stack along [100].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803015526/su6035sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803015526/su6035Isup2.hkl
Contains datablock I

CCDC reference: 189044

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.049
  • wR factor = 0.107
  • Data-to-parameter ratio = 16.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
CELLV_02 Alert C The supplied cell volume s.u. differs from that calculated from the cell parameter s.u.'s by > 2 Calculated cell volume su = 14.42 Cell volume su given = 12.00
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: XSCANS (Bruker, 1996); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1998); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

N'-(2-Chlorobenzoyl)-N-(pyrrolidin-1-yl)thiourea top
Crystal data top
C12H13ClN2OSZ = 2
Mr = 268.75F(000) = 280
Triclinic, P1Dx = 1.412 Mg m3
a = 7.299 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.039 (1) ÅCell parameters from 25 reflections
c = 10.096 (1) Åθ = 7.1–15.9°
α = 67.03 (1)°µ = 0.45 mm1
β = 69.32 (1)°T = 293 K
γ = 88.43 (1)°Prism, colourless
V = 631.98 (12) Å30.28 × 0.25 × 0.12 mm
Data collection top
Bruker P4
diffractometer
1692 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 26.4°, θmin = 2.2°
ω scansh = 19
Absorption correction: ψ scan
(North et al., 1968)
k = 1212
Tmin = 0.867, Tmax = 0.947l = 1111
3181 measured reflections3 standard reflections every 397 reflections
2552 independent reflections intensity decay: <1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.107 w = 1/[σ2(Fo2) + (0.0363P)2 + 0.1907P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
2552 reflectionsΔρmax = 0.28 e Å3
155 parametersΔρmin = 0.29 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.049 (4)
Special details top

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. The H atoms were introduced at calculated positions as riding atoms, with bond lengths of 0.86(N—H), 0.93(CH-aromatic), and 0.97(CH2) Å. The isotropic displacement parameters, Uiso(H), were made equal to = 1.2Ueq(parent atom).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.39682 (13)0.25002 (11)1.00157 (10)0.0649 (3)
S10.44259 (12)0.36357 (8)0.38561 (9)0.0437 (2)
O10.7075 (3)0.1040 (2)0.6929 (3)0.0551 (6)
N10.5182 (3)0.2874 (2)0.6433 (3)0.0344 (6)
H1A0.48430.36420.65920.041*
N20.3313 (3)0.1124 (2)0.6317 (3)0.0375 (6)
C10.6417 (4)0.3265 (3)0.8918 (3)0.0408 (7)
C20.7294 (5)0.4102 (3)0.9388 (4)0.0534 (9)
H2A0.65820.42541.02720.064*
C30.9232 (6)0.4711 (4)0.8538 (4)0.0578 (9)
H3A0.98160.53130.88220.069*
C41.0311 (5)0.4432 (4)0.7267 (4)0.0558 (9)
H4A1.16330.48200.67130.067*
C50.9427 (4)0.3576 (3)0.6818 (4)0.0442 (8)
H5A1.01630.33850.59640.053*
C60.7460 (4)0.2999 (3)0.7620 (3)0.0341 (6)
C70.6550 (4)0.2174 (3)0.6996 (3)0.0354 (6)
C80.4279 (4)0.2444 (3)0.5614 (3)0.0328 (6)
C90.2289 (5)0.0538 (3)0.5592 (4)0.0460 (8)
H9A0.32270.04270.46940.055*
H9B0.13600.11760.52770.055*
C100.1226 (5)0.0927 (4)0.6850 (4)0.0601 (10)
H10A0.20370.16990.67880.072*
H10B0.00120.11530.67800.072*
C110.0872 (5)0.0731 (4)0.8337 (4)0.0573 (9)
H11A0.02430.01990.85670.069*
H11B0.06400.16640.92090.069*
C120.2788 (5)0.0141 (3)0.7962 (4)0.0498 (8)
H12A0.25960.06870.85990.060*
H12B0.37970.04880.81070.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0469 (5)0.0841 (7)0.0530 (5)0.0094 (5)0.0019 (4)0.0310 (5)
S10.0517 (5)0.0422 (4)0.0400 (4)0.0023 (4)0.0218 (4)0.0150 (3)
O10.0494 (14)0.0498 (13)0.0901 (18)0.0203 (11)0.0399 (13)0.0410 (13)
N10.0399 (14)0.0316 (12)0.0432 (14)0.0099 (11)0.0236 (12)0.0199 (11)
N20.0387 (14)0.0352 (13)0.0423 (14)0.0009 (11)0.0197 (12)0.0150 (11)
C10.0387 (17)0.0429 (16)0.0384 (16)0.0020 (14)0.0160 (14)0.0124 (13)
C20.063 (2)0.060 (2)0.0463 (19)0.0030 (18)0.0267 (18)0.0246 (17)
C30.070 (3)0.055 (2)0.066 (2)0.0018 (19)0.044 (2)0.0256 (18)
C40.0405 (19)0.062 (2)0.064 (2)0.0054 (16)0.0235 (18)0.0204 (18)
C50.0353 (17)0.0519 (19)0.0508 (18)0.0052 (14)0.0178 (15)0.0246 (16)
C60.0326 (16)0.0328 (14)0.0405 (16)0.0047 (12)0.0199 (13)0.0130 (12)
C70.0304 (16)0.0372 (16)0.0384 (16)0.0041 (13)0.0132 (13)0.0149 (13)
C80.0281 (15)0.0359 (15)0.0394 (15)0.0079 (12)0.0133 (13)0.0199 (13)
C90.0472 (19)0.0475 (18)0.056 (2)0.0051 (15)0.0249 (16)0.0293 (16)
C100.054 (2)0.048 (2)0.084 (3)0.0025 (17)0.029 (2)0.0298 (19)
C110.047 (2)0.0474 (19)0.066 (2)0.0070 (16)0.0209 (18)0.0106 (17)
C120.049 (2)0.0442 (17)0.0520 (19)0.0023 (15)0.0232 (16)0.0109 (15)
Geometric parameters (Å, º) top
Cl1—C11.739 (3)C4—H4A0.9300
S1—C81.676 (3)C5—C61.382 (4)
O1—C71.211 (3)C5—H5A0.9300
N1—C71.366 (3)C6—C71.502 (4)
N1—C81.408 (3)C9—C101.513 (4)
N1—H1A0.8600C9—H9A0.9700
N2—C81.312 (3)C9—H9B0.9700
N2—C121.473 (4)C10—C111.521 (5)
N2—C91.478 (3)C10—H10A0.9700
C1—C21.376 (4)C10—H10B0.9700
C1—C61.388 (4)C11—C121.517 (4)
C2—C31.375 (5)C11—H11A0.9700
C2—H2A0.9300C11—H11B0.9700
C3—C41.379 (5)C12—H12A0.9700
C3—H3A0.9300C12—H12B0.9700
C4—C51.378 (4)
C7—N1—C8125.5 (2)N2—C8—N1116.7 (2)
C7—N1—H1A117.2N2—C8—S1124.0 (2)
C8—N1—H1A117.2N1—C8—S1119.23 (19)
C8—N2—C12126.4 (2)N2—C9—C10104.3 (2)
C8—N2—C9122.3 (2)N2—C9—H9A110.9
C12—N2—C9110.4 (2)C10—C9—H9A110.9
C2—C1—C6121.3 (3)N2—C9—H9B110.9
C2—C1—Cl1118.6 (2)C10—C9—H9B110.9
C6—C1—Cl1120.0 (2)H9A—C9—H9B108.9
C3—C2—C1119.4 (3)C9—C10—C11103.4 (3)
C3—C2—H2A120.3C9—C10—H10A111.1
C1—C2—H2A120.3C11—C10—H10A111.1
C2—C3—C4120.2 (3)C9—C10—H10B111.1
C2—C3—H3A119.9C11—C10—H10B111.1
C4—C3—H3A119.9H10A—C10—H10B109.1
C5—C4—C3119.9 (3)C12—C11—C10102.6 (3)
C5—C4—H4A120.1C12—C11—H11A111.2
C3—C4—H4A120.1C10—C11—H11A111.2
C4—C5—C6120.9 (3)C12—C11—H11B111.2
C4—C5—H5A119.6C10—C11—H11B111.2
C6—C5—H5A119.6H11A—C11—H11B109.2
C5—C6—C1118.2 (3)N2—C12—C11102.7 (2)
C5—C6—C7118.1 (3)N2—C12—H12A111.2
C1—C6—C7123.7 (3)C11—C12—H12A111.2
O1—C7—N1124.0 (3)N2—C12—H12B111.2
O1—C7—C6122.5 (3)C11—C12—H12B111.2
N1—C7—C6113.4 (2)H12A—C12—H12B109.1
C6—C1—C2—C31.2 (5)C5—C6—C7—N1111.3 (3)
Cl1—C1—C2—C3179.8 (2)C1—C6—C7—N166.0 (3)
C1—C2—C3—C42.9 (5)C12—N2—C8—N111.3 (4)
C2—C3—C4—C52.0 (5)C9—N2—C8—N1179.7 (2)
C3—C4—C5—C60.5 (5)C12—N2—C8—S1166.7 (2)
C4—C5—C6—C12.1 (4)C9—N2—C8—S11.7 (4)
C4—C5—C6—C7175.4 (3)C7—N1—C8—N257.7 (4)
C2—C1—C6—C51.2 (4)C7—N1—C8—S1124.2 (2)
Cl1—C1—C6—C5177.3 (2)C8—N2—C9—C10174.5 (3)
C2—C1—C6—C7176.1 (3)C12—N2—C9—C104.4 (3)
Cl1—C1—C6—C75.4 (4)N2—C9—C10—C1127.6 (3)
C8—N1—C7—O14.2 (4)C9—C10—C11—C1240.2 (3)
C8—N1—C7—C6171.8 (2)C8—N2—C12—C11149.1 (3)
C5—C6—C7—O164.8 (4)C9—N2—C12—C1120.5 (3)
C1—C6—C7—O1117.9 (3)C10—C11—C12—N236.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···S1i0.862.633.412 (3)152
C12—H12B···O10.972.502.968 (5)109
Symmetry code: (i) x+1, y+1, z+1.
 

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