1-(4-Chloro­thiobenzoyl)piperidine

In the title compound, C₁₂H₁₄ClNS, the piperidine ring adopts a chair conformation and the crystal structure is stabilized by C—H...Cl inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.030
• wR factor = 0.084
• Data-to-parameter ratio = 9.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT048_ALERT_1_C MoietyFormula Not Given ........................          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.94
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT480_ALERT_4_C Long H...A H-Bond Reported H6B    ..  CL      ..       2.91 Ang.

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.935
            Tmax scaled      0.934 Tmin scaled      0.809
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           24.99
           From the CIF: _reflns_number_total               1316
           Count of symmetry unique reflns         1270
           Completeness (_total/calc)            103.62%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured        46
           Fraction of Friedel pairs measured     0.036
           Are heavy atom types Z>Si present        yes
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL/PC (Bruker, 2000); program(s) used to refine structure: SHELXTL/PC; molecular graphics: SHELXTL/PC and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL/PC.

Piperidin-4-chloro-phenyl-methanethione

Crystal data

C12H14ClNS	F(000) = 504
Mr = 239.75	Dx = 1.321 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 6.2251 (9) Å	θ = 9.6–13.2°
b = 7.7283 (11) Å	µ = 0.46 mm^−1
c = 25.061 (3) Å	T = 293 K
V = 1205.7 (3) Å^3	Needle, yellow
Z = 4	0.25 × 0.18 × 0.15 mm

Data collection

MACH3-Nonius sealed tube diffractometer	1046 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.004
Graphite monochromator	θmax = 25.0°, θmin = 2.8°
ω–2θ scans	h = 0→7
Absorption correction: ψ scan [North et al., 1968]	k = 0→9
Tmin = 0.866, Tmax = 0.999	l = −1→29
1333 measured reflections	3 standard reflections every 60 min
1316 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.030	H-atom parameters constrained
wR(F^2) = 0.084	w = 1/[σ^2(Fo^2) + (0.0293P)^2 + 0.5735P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
1316 reflections	Δρmax = 0.19 e Å^−3
136 parameters	Δρmin = −0.17 e Å^−3
0 restraints	Absolute structure: Flack (1983), 45 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.20 (15)

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
N	0.6313 (5)	0.6338 (4)	0.39436 (12)	0.0526 (8)
C2	0.8002 (6)	0.6106 (6)	0.43421 (15)	0.0631 (11)
H2A	0.8794	0.7178	0.4384	0.076*
H2B	0.8997	0.5222	0.4223	0.076*
C3	0.7039 (7)	0.5581 (6)	0.48726 (15)	0.0691 (12)
H3A	0.6176	0.6525	0.5011	0.083*
H3B	0.8185	0.5357	0.5126	0.083*
C4	0.5651 (7)	0.3977 (6)	0.48196 (16)	0.0699 (12)
H4A	0.6551	0.2985	0.4740	0.084*
H4B	0.4920	0.3757	0.5155	0.084*
C5	0.4007 (6)	0.4212 (6)	0.43791 (16)	0.0626 (11)
H5A	0.3242	0.3133	0.4325	0.075*
H5B	0.2971	0.5083	0.4486	0.075*
C6	0.5049 (6)	0.4756 (5)	0.38641 (14)	0.0530 (9)
H6A	0.5977	0.3836	0.3737	0.064*
H6B	0.3952	0.4960	0.3597	0.064*
C7	0.5750 (6)	0.7885 (5)	0.37609 (13)	0.0450 (9)
S	0.6745 (2)	0.97581 (13)	0.39812 (4)	0.0639 (3)
C8	0.4228 (6)	0.7934 (5)	0.33013 (13)	0.0428 (8)
C9	0.2261 (6)	0.8756 (5)	0.33456 (15)	0.0541 (10)
H9	0.1857	0.9241	0.3670	0.065*
C10	0.0904 (6)	0.8865 (5)	0.29169 (15)	0.0561 (10)
H10	−0.0424	0.9404	0.2951	0.067*
C11	0.1524 (6)	0.8168 (5)	0.24348 (14)	0.0482 (9)
Cl	−0.01798 (18)	0.83831 (15)	0.18863 (4)	0.0723 (3)
C12	0.3450 (6)	0.7325 (4)	0.23778 (13)	0.0466 (9)
H12	0.3846	0.6848	0.2052	0.056*
C13	0.4787 (6)	0.7202 (4)	0.28152 (13)	0.0467 (9)
H13	0.6087	0.6618	0.2784	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N	0.0502 (18)	0.0525 (18)	0.0550 (18)	−0.0052 (16)	−0.0174 (16)	0.0003 (17)
C2	0.052 (2)	0.072 (3)	0.066 (3)	−0.002 (2)	−0.019 (2)	−0.002 (2)
C3	0.065 (3)	0.087 (3)	0.055 (3)	0.015 (3)	−0.016 (2)	−0.011 (2)
C4	0.073 (3)	0.084 (3)	0.053 (2)	0.004 (3)	−0.001 (2)	0.014 (2)
C5	0.054 (2)	0.059 (3)	0.075 (3)	−0.003 (2)	−0.005 (2)	0.007 (2)
C6	0.057 (2)	0.0470 (19)	0.055 (2)	0.000 (2)	−0.017 (2)	−0.0007 (18)
C7	0.0445 (19)	0.049 (2)	0.0417 (18)	−0.0056 (18)	0.0054 (16)	−0.0013 (17)
S	0.0785 (7)	0.0552 (6)	0.0580 (6)	−0.0169 (6)	0.0010 (6)	−0.0113 (5)
C8	0.0449 (19)	0.0386 (18)	0.0449 (18)	−0.0013 (16)	0.0031 (16)	0.0029 (16)
C9	0.053 (2)	0.056 (2)	0.053 (2)	0.006 (2)	0.0075 (18)	−0.0071 (19)
C10	0.047 (2)	0.055 (2)	0.066 (2)	0.011 (2)	0.001 (2)	−0.001 (2)
C11	0.049 (2)	0.0418 (19)	0.054 (2)	0.000 (2)	−0.0076 (18)	0.0114 (18)
Cl	0.0670 (6)	0.0822 (7)	0.0678 (6)	0.0088 (6)	−0.0204 (6)	0.0155 (6)
C12	0.053 (2)	0.045 (2)	0.0418 (18)	0.004 (2)	0.0021 (18)	0.0001 (16)
C13	0.0421 (19)	0.046 (2)	0.052 (2)	0.0078 (19)	−0.0001 (17)	−0.0007 (17)

Geometric parameters (Å, º)

N—C7	1.327 (4)	C6—H6A	0.9700
N—C2	1.461 (4)	C6—H6B	0.9700
N—C6	1.468 (4)	C7—C8	1.492 (5)
C2—C3	1.514 (6)	C7—S	1.669 (4)
C2—H2A	0.9700	C8—C9	1.384 (5)
C2—H2B	0.9700	C8—C13	1.387 (4)
C3—C4	1.517 (6)	C9—C10	1.369 (5)
C3—H3A	0.9700	C9—H9	0.9300
C3—H3B	0.9700	C10—C11	1.378 (5)
C4—C5	1.516 (5)	C10—H10	0.9300
C4—H4A	0.9700	C11—C12	1.372 (5)
C4—H4B	0.9700	C11—Cl	1.744 (3)
C5—C6	1.504 (5)	C12—C13	1.379 (5)
C5—H5A	0.9700	C12—H12	0.9300
C5—H5B	0.9700	C13—H13	0.9300
C7—N—C2	122.4 (3)	N—C6—C5	110.3 (3)
C7—N—C6	124.2 (3)	N—C6—H6A	109.6
C2—N—C6	112.1 (3)	C5—C6—H6A	109.6
N—C2—C3	110.4 (3)	N—C6—H6B	109.6
N—C2—H2A	109.6	C5—C6—H6B	109.6
C3—C2—H2A	109.6	H6A—C6—H6B	108.1
N—C2—H2B	109.6	N—C7—C8	117.2 (3)
C3—C2—H2B	109.6	N—C7—S	124.7 (3)
H2A—C2—H2B	108.1	C8—C7—S	118.0 (3)
C2—C3—C4	111.6 (3)	C9—C8—C13	118.7 (3)
C2—C3—H3A	109.3	C9—C8—C7	120.8 (3)
C4—C3—H3A	109.3	C13—C8—C7	120.5 (3)
C2—C3—H3B	109.3	C10—C9—C8	120.7 (3)
C4—C3—H3B	109.3	C10—C9—H9	119.6
H3A—C3—H3B	108.0	C8—C9—H9	119.6
C5—C4—C3	110.5 (4)	C9—C10—C11	119.4 (4)
C5—C4—H4A	109.6	C9—C10—H10	120.3
C3—C4—H4A	109.6	C11—C10—H10	120.3
C5—C4—H4B	109.6	C12—C11—C10	121.5 (3)
C3—C4—H4B	109.6	C12—C11—Cl	119.6 (3)
H4A—C4—H4B	108.1	C10—C11—Cl	118.9 (3)
C6—C5—C4	111.6 (3)	C11—C12—C13	118.5 (3)
C6—C5—H5A	109.3	C11—C12—H12	120.8
C4—C5—H5A	109.3	C13—C12—H12	120.8
C6—C5—H5B	109.3	C12—C13—C8	121.2 (3)
C4—C5—H5B	109.3	C12—C13—H13	119.4
H5A—C5—H5B	108.0	C8—C13—H13	119.4
C7—N—C2—C3	108.7 (4)	S—C7—C8—C9	−63.7 (4)
C6—N—C2—C3	−59.0 (5)	N—C7—C8—C13	−61.7 (5)
N—C2—C3—C4	55.2 (5)	S—C7—C8—C13	114.3 (3)
C2—C3—C4—C5	−52.3 (5)	C13—C8—C9—C10	−0.8 (6)
C3—C4—C5—C6	52.8 (5)	C7—C8—C9—C10	177.2 (4)
C7—N—C6—C5	−107.9 (4)	C8—C9—C10—C11	−1.0 (6)
C2—N—C6—C5	59.5 (4)	C9—C10—C11—C12	1.8 (6)
C4—C5—C6—N	−56.0 (4)	C9—C10—C11—Cl	−177.7 (3)
C2—N—C7—C8	171.6 (3)	C10—C11—C12—C13	−0.8 (5)
C6—N—C7—C8	−22.3 (5)	Cl—C11—C12—C13	178.8 (3)
C2—N—C7—S	−4.1 (5)	C11—C12—C13—C8	−1.0 (5)
C6—N—C7—S	162.0 (3)	C9—C8—C13—C12	1.8 (5)
N—C7—C8—C9	120.3 (4)	C7—C8—C13—C12	−176.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6B···Cl^i	0.97	2.91	3.721 (4)	142

Symmetry code: (i) −x, y−1/2, −z+1/2.