N′-(4-Chloro­benzoyl)-N-(pyrrolidin-1-yl)­thio­urea

The title compound, C₁₂H₁₃ClN₂OS, shows a twisted conform­ation with respect to the carbonyl and thio­carbonyl moieties. The crystal packing is determined by strong intermolecular N—H...O interactions.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.033
• wR factor = 0.081
• Data-to-parameter ratio = 13.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           26.37
         From the CIF: _reflns_number_total               2054
         Count of symmetry unique reflns         1372
         Completeness (_total/calc)            149.71%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured       682
         Fraction of Friedel pairs measured     0.497
         Are heavy atom types Z>Si present          yes
          WARNING: Large fraction of Friedel related reflns may
                   be needed to determine absolute structure

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SMART; data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

N'-(4-Chlorobenzoyl)-N-(pyrrolidin-1-yl)thiourea

Crystal data

C12H13ClN2OS	Dx = 1.402 Mg m^−3
Mr = 268.75	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 3606 reflections
a = 7.8623 (7) Å	θ = 2.3–28.2°
b = 14.2934 (13) Å	µ = 0.45 mm^−1
c = 11.3321 (10) Å	T = 150 K
V = 1273.5 (2) Å^3	Prism, colorless
Z = 4	0.40 × 0.35 × 0.32 mm
F(000) = 560

Data collection

Bruker CCD area-detector diffractometer	2054 independent reflections
Radiation source: sealed tube	1958 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 26.4°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −9→9
Tmin = 0.839, Tmax = 0.871	k = −17→17
6878 measured reflections	l = −10→14

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.081	w = 1/[σ^2(Fo^2) + (0.0515P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
2054 reflections	Δρmax = 0.48 e Å^−3
158 parameters	Δρmin = −0.15 e Å^−3
1 restraint	Absolute structure: Flack (1983), 0000 Friedel reflections
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (6)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	−0.07452 (10)	0.09524 (5)	0.08844 (6)	0.0525 (2)
S1	0.41492 (7)	0.37004 (4)	0.72876 (6)	0.03008 (15)
O1	0.53370 (19)	0.15508 (11)	0.50003 (14)	0.0288 (4)
N1	0.3117 (2)	0.23361 (12)	0.58396 (16)	0.0238 (4)
H1	0.228 (4)	0.2673 (17)	0.559 (2)	0.038 (7)*
N2	0.4410 (2)	0.18626 (13)	0.75789 (16)	0.0254 (4)
C1	0.3315 (3)	0.16281 (17)	0.2805 (2)	0.0317 (5)
H1A	0.4469	0.1792	0.2670	0.038*
C2	0.2267 (3)	0.14374 (17)	0.1860 (2)	0.0380 (6)
H2A	0.2683	0.1485	0.1075	0.046*
C3	0.0593 (3)	0.11747 (16)	0.2072 (2)	0.0328 (6)
C4	−0.0035 (3)	0.10984 (15)	0.3208 (2)	0.0332 (5)
H4A	−0.1175	0.0903	0.3338	0.040*
C5	0.1016 (3)	0.13099 (15)	0.4158 (2)	0.0284 (5)
H5A	0.0591	0.1268	0.4941	0.034*
C6	0.2694 (3)	0.15828 (14)	0.39602 (19)	0.0249 (4)
C7	0.3839 (3)	0.18159 (15)	0.49700 (19)	0.0242 (4)
C8	0.3925 (2)	0.25781 (16)	0.69154 (19)	0.0242 (4)
C9	0.5193 (3)	0.19962 (17)	0.8754 (2)	0.0306 (5)
H9A	0.4455	0.2382	0.9268	0.037*
H9B	0.6319	0.2301	0.8685	0.037*
C10	0.5364 (3)	0.10125 (19)	0.9237 (2)	0.0376 (6)
H10A	0.5220	0.1006	1.0105	0.045*
H10B	0.6489	0.0744	0.9038	0.045*
C11	0.3934 (3)	0.04697 (17)	0.8630 (2)	0.0356 (5)
H11A	0.4157	−0.0212	0.8638	0.043*
H11B	0.2821	0.0595	0.9006	0.043*
C12	0.4001 (3)	0.08618 (15)	0.7381 (2)	0.0314 (5)
H12A	0.4896	0.0550	0.6909	0.038*
H12B	0.2893	0.0789	0.6976	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0686 (5)	0.0486 (4)	0.0405 (4)	−0.0098 (3)	−0.0335 (3)	0.0019 (3)
S1	0.0326 (3)	0.0286 (3)	0.0290 (3)	−0.0033 (2)	0.0028 (2)	−0.0062 (2)
O1	0.0214 (7)	0.0371 (9)	0.0280 (9)	0.0013 (6)	−0.0016 (6)	−0.0083 (7)
N1	0.0200 (9)	0.0303 (9)	0.0210 (9)	0.0033 (7)	−0.0026 (7)	−0.0019 (7)
N2	0.0230 (8)	0.0317 (10)	0.0214 (10)	−0.0009 (7)	−0.0021 (7)	−0.0026 (7)
C1	0.0286 (12)	0.0411 (13)	0.0252 (11)	−0.0030 (10)	0.0010 (9)	−0.0034 (9)
C2	0.0494 (15)	0.0432 (14)	0.0213 (11)	−0.0032 (11)	−0.0020 (11)	−0.0027 (10)
C3	0.0407 (14)	0.0285 (11)	0.0292 (14)	−0.0025 (9)	−0.0164 (10)	−0.0007 (10)
C4	0.0298 (12)	0.0335 (12)	0.0362 (13)	−0.0070 (9)	−0.0083 (10)	0.0031 (10)
C5	0.0305 (12)	0.0308 (14)	0.0240 (12)	−0.0030 (9)	−0.0025 (9)	0.0002 (8)
C6	0.0248 (10)	0.0262 (11)	0.0238 (10)	−0.0004 (8)	−0.0030 (9)	−0.0025 (8)
C7	0.0256 (10)	0.0255 (11)	0.0215 (10)	−0.0034 (8)	−0.0014 (8)	−0.0006 (8)
C8	0.0167 (10)	0.0337 (12)	0.0221 (10)	0.0003 (8)	0.0022 (8)	−0.0021 (8)
C9	0.0233 (11)	0.0478 (13)	0.0207 (11)	−0.0026 (9)	−0.0048 (9)	−0.0026 (10)
C10	0.0271 (11)	0.0582 (18)	0.0276 (14)	0.0023 (11)	−0.0035 (10)	0.0080 (10)
C11	0.0288 (12)	0.0389 (13)	0.0391 (13)	0.0023 (9)	−0.0024 (10)	0.0089 (11)
C12	0.0339 (12)	0.0279 (11)	0.0324 (12)	0.0006 (8)	−0.0053 (10)	0.0003 (10)

Geometric parameters (Å, º)

Cl1—C3	1.738 (2)	C4—H4A	0.9500
S1—C8	1.668 (2)	C5—C6	1.394 (3)
O1—C7	1.238 (3)	C5—H5A	0.9500
N1—C7	1.359 (3)	C6—C7	1.493 (3)
N1—C8	1.417 (3)	C9—C10	1.515 (3)
N1—H1	0.86 (3)	C9—H9A	0.9900
N2—C8	1.325 (3)	C9—H9B	0.9900
N2—C9	1.479 (3)	C10—C11	1.530 (4)
N2—C12	1.483 (3)	C10—H10A	0.9900
C1—C2	1.378 (3)	C10—H10B	0.9900
C1—C6	1.398 (3)	C11—C12	1.522 (4)
C1—H1A	0.9500	C11—H11A	0.9900
C2—C3	1.390 (4)	C11—H11B	0.9900
C2—H2A	0.9500	C12—H12A	0.9900
C3—C4	1.383 (4)	C12—H12B	0.9900
C4—C5	1.390 (3)
C7—N1—C8	124.76 (17)	N2—C8—N1	115.38 (19)
C7—N1—H1	113.1 (18)	N2—C8—S1	124.63 (17)
C8—N1—H1	118.9 (18)	N1—C8—S1	119.96 (16)
C8—N2—C9	122.06 (19)	N2—C9—C10	104.03 (19)
C8—N2—C12	126.60 (19)	N2—C9—H9A	111.0
C9—N2—C12	110.51 (18)	C10—C9—H9A	111.0
C2—C1—C6	120.7 (2)	N2—C9—H9B	111.0
C2—C1—H1A	119.7	C10—C9—H9B	111.0
C6—C1—H1A	119.7	H9A—C9—H9B	109.0
C1—C2—C3	119.0 (2)	C9—C10—C11	104.05 (19)
C1—C2—H2A	120.5	C9—C10—H10A	110.9
C3—C2—H2A	120.5	C11—C10—H10A	110.9
C4—C3—C2	121.4 (2)	C9—C10—H10B	110.9
C4—C3—Cl1	119.34 (18)	C11—C10—H10B	110.9
C2—C3—Cl1	119.3 (2)	H10A—C10—H10B	109.0
C3—C4—C5	119.4 (2)	C12—C11—C10	101.87 (19)
C3—C4—H4A	120.3	C12—C11—H11A	111.4
C5—C4—H4A	120.3	C10—C11—H11A	111.4
C4—C5—C6	119.9 (2)	C12—C11—H11B	111.4
C4—C5—H5A	120.0	C10—C11—H11B	111.4
C6—C5—H5A	120.0	H11A—C11—H11B	109.3
C5—C6—C1	119.6 (2)	N2—C12—C11	102.8 (2)
C5—C6—C7	120.6 (2)	N2—C12—H12A	111.2
C1—C6—C7	119.79 (19)	C11—C12—H12A	111.2
O1—C7—N1	123.0 (2)	N2—C12—H12B	111.2
O1—C7—C6	121.8 (2)	C11—C12—H12B	111.2
N1—C7—C6	115.21 (18)	H12A—C12—H12B	109.1
C6—C1—C2—C3	−1.7 (4)	C1—C6—C7—N1	138.5 (2)
C1—C2—C3—C4	−0.2 (4)	C9—N2—C8—N1	−176.88 (17)
C1—C2—C3—Cl1	178.92 (19)	C12—N2—C8—N1	−8.3 (3)
C2—C3—C4—C5	1.5 (3)	C9—N2—C8—S1	1.1 (3)
Cl1—C3—C4—C5	−177.62 (18)	C12—N2—C8—S1	169.65 (16)
C3—C4—C5—C6	−0.9 (3)	C7—N1—C8—N2	−59.6 (3)
C4—C5—C6—C1	−1.0 (3)	C7—N1—C8—S1	122.3 (2)
C4—C5—C6—C7	179.8 (2)	C8—N2—C9—C10	174.26 (19)
C2—C1—C6—C5	2.3 (3)	C12—N2—C9—C10	4.0 (2)
C2—C1—C6—C7	−178.4 (2)	N2—C9—C10—C11	−27.5 (2)
C8—N1—C7—O1	−5.0 (3)	C9—C10—C11—C12	40.3 (2)
C8—N1—C7—C6	175.09 (19)	C8—N2—C12—C11	−148.7 (2)
C5—C6—C7—O1	137.8 (2)	C9—N2—C12—C11	21.0 (2)
C1—C6—C7—O1	−41.4 (3)	C10—C11—C12—N2	−37.0 (2)
C5—C6—C7—N1	−42.3 (3)