4-(Benzo­[b]­thio­phen-3-yl)-1-methyl­piperidine-4-carbo­nitrile

Crystals of the title compound, C₁₅H₁₆N₂S, were obtained from the reaction of benzo­[b]­thio­phene-3-aceto­nitrile with mechloreth­amine and subsequent crystallization of the product from hexane..

Key indicators

• Single-crystal X-ray study
• T = 90 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.044
• wR factor = 0.098
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _reflns_number_total               2251
           Count of symmetry unique reflns         1275
           Completeness (_total/calc)            176.55%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       976
           Fraction of Friedel pairs measured     0.765
           Are heavy atom types Z>Si present          yes

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

   1 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO–SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1995); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and local procedures.

4-(Benzo[b]thiophen-3-yl)-1-methylpiperidine-4-carbonitrile

Crystal data

C15H16N2S	F(000) = 544
Mr = 256.36	Dx = 1.284 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2635 reflections
a = 18.1809 (4) Å	θ = 1.0–25.4°
b = 10.6493 (3) Å	µ = 0.23 mm^−1
c = 6.8470 (8) Å	T = 90 K
V = 1325.67 (16) Å^3	Rod, colourless
Z = 4	0.25 × 0.10 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer	2251 independent reflections
Radiation source: fine-focus sealed tube	1762 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
Detector resolution: 18 pixels mm^-1	θmax = 25.0°, θmin = 1.9°
ω scans at fixed χ = 55°	h = −21→21
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −12→12
Tmin = 0.945, Tmax = 0.983	l = −7→8
4182 measured reflections

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)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.049P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
2251 reflections	Δρmax = 0.23 e Å^−3
164 parameters	Δρmin = −0.27 e Å^−3
1 restraint	Absolute structure: Flack (1983), 976 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (10)

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
S1	0.31105 (4)	1.01343 (7)	0.95464 (14)	0.0298 (2)
C1	0.36630 (13)	0.7932 (3)	1.0176 (4)	0.0209 (8)
C2	0.31863 (13)	0.8780 (3)	1.0903 (5)	0.0252 (8)
H2	0.2915	0.8642	1.2069	0.030*
C3	0.37470 (14)	0.9580 (2)	0.7870 (5)	0.0235 (8)
C4	0.39983 (16)	1.0206 (3)	0.6222 (5)	0.0296 (8)
H4	0.3809	1.1007	0.5880	0.035*
C5	0.45304 (16)	0.9636 (3)	0.5089 (5)	0.0327 (9)
H5	0.4705	1.0043	0.3945	0.039*
C6	0.48143 (15)	0.8463 (3)	0.5615 (5)	0.0270 (8)
H6	0.5190	0.8095	0.4839	0.032*
C7	0.45610 (14)	0.7830 (3)	0.7232 (4)	0.0218 (7)
H7	0.4756	0.7029	0.7560	0.026*
C8	0.40054 (13)	0.8385 (3)	0.8405 (5)	0.0217 (7)
C9	0.38100 (13)	0.6656 (3)	1.1101 (4)	0.0203 (7)
C10	0.33907 (14)	0.6502 (3)	1.3044 (5)	0.0253 (8)
H10A	0.3580	0.7119	1.4001	0.030*
H10B	0.2863	0.6684	1.2827	0.030*
C11	0.34695 (15)	0.5191 (3)	1.3880 (4)	0.0243 (8)
H11A	0.3994	0.5020	1.4169	0.029*
H11B	0.3190	0.5129	1.5118	0.029*
N12	0.31928 (11)	0.4257 (2)	1.2489 (4)	0.0245 (6)
C13	0.36314 (15)	0.4305 (3)	1.0699 (5)	0.0255 (8)
H13A	0.3457	0.3649	0.9786	0.031*
H13B	0.4152	0.4125	1.1017	0.031*
C14	0.35804 (14)	0.5571 (2)	0.9719 (5)	0.0213 (7)
H14A	0.3069	0.5711	0.9275	0.026*
H14B	0.3902	0.5577	0.8552	0.026*
C15	0.32203 (14)	0.3011 (3)	1.3354 (6)	0.0330 (8)
H15A	0.3733	0.2783	1.3619	0.050*
H15B	0.3005	0.2400	1.2448	0.050*
H15C	0.2941	0.3008	1.4579	0.050*
C16	0.46120 (15)	0.6537 (3)	1.1516 (5)	0.0215 (7)
N16	0.52267 (12)	0.6430 (2)	1.1839 (4)	0.0303 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0263 (4)	0.0242 (4)	0.0390 (5)	0.0044 (3)	−0.0016 (4)	−0.0008 (5)
C1	0.0154 (13)	0.0219 (17)	0.026 (2)	−0.0001 (12)	−0.0021 (13)	0.0007 (14)
C2	0.0247 (16)	0.0220 (18)	0.029 (2)	−0.0004 (13)	0.0029 (14)	0.0005 (16)
C3	0.0198 (16)	0.0202 (17)	0.031 (2)	−0.0029 (13)	−0.0054 (14)	−0.0009 (16)
C4	0.0301 (17)	0.0252 (18)	0.033 (2)	−0.0058 (13)	−0.0087 (17)	0.0071 (17)
C5	0.0306 (17)	0.038 (2)	0.029 (2)	−0.0148 (14)	−0.0040 (16)	0.0038 (17)
C6	0.0250 (15)	0.0290 (19)	0.027 (2)	−0.0084 (14)	0.0024 (14)	−0.0022 (17)
C7	0.0205 (15)	0.0195 (16)	0.025 (2)	−0.0031 (13)	−0.0003 (14)	−0.0018 (15)
C8	0.0185 (14)	0.0203 (18)	0.0264 (19)	−0.0021 (13)	−0.0061 (15)	0.0001 (15)
C9	0.0161 (14)	0.0198 (16)	0.0250 (19)	−0.0004 (12)	0.0024 (13)	0.0026 (15)
C10	0.0171 (13)	0.0310 (19)	0.0277 (19)	0.0000 (12)	0.0012 (14)	0.0014 (18)
C11	0.0184 (13)	0.0330 (19)	0.0214 (19)	0.0036 (13)	0.0003 (13)	0.0042 (15)
N12	0.0272 (14)	0.0223 (14)	0.0240 (15)	−0.0017 (11)	0.0006 (12)	0.0040 (14)
C13	0.0218 (16)	0.0256 (18)	0.0291 (19)	−0.0002 (13)	−0.0016 (14)	−0.0014 (16)
C14	0.0154 (14)	0.0238 (15)	0.0248 (18)	−0.0005 (11)	−0.0002 (14)	0.0021 (16)
C15	0.0340 (17)	0.0245 (19)	0.041 (2)	−0.0002 (14)	0.0006 (16)	0.0086 (17)
C16	0.0245 (16)	0.0180 (16)	0.0220 (18)	0.0004 (13)	0.0030 (14)	−0.0036 (15)
N16	0.0220 (14)	0.0375 (16)	0.0314 (18)	0.0033 (12)	0.0021 (14)	−0.0046 (14)

Geometric parameters (Å, º)

S1—C2	1.722 (3)	C9—C14	1.551 (4)
S1—C3	1.733 (3)	C10—C11	1.517 (4)
C1—C2	1.347 (4)	C10—H10A	0.9900
C1—C8	1.446 (4)	C10—H10B	0.9900
C1—C9	1.522 (4)	C11—N12	1.466 (4)
C2—H2	0.9500	C11—H11A	0.9900
C3—C4	1.388 (4)	C11—H11B	0.9900
C3—C8	1.406 (4)	N12—C15	1.455 (4)
C4—C5	1.380 (5)	N12—C13	1.463 (4)
C4—H4	0.9500	C13—C14	1.509 (4)
C5—C6	1.399 (4)	C13—H13A	0.9900
C5—H5	0.9500	C13—H13B	0.9900
C6—C7	1.376 (4)	C14—H14A	0.9900
C6—H6	0.9500	C14—H14B	0.9900
C7—C8	1.419 (4)	C15—H15A	0.9800
C7—H7	0.9500	C15—H15B	0.9800
C9—C16	1.491 (4)	C15—H15C	0.9800
C9—C10	1.542 (4)	C16—N16	1.145 (3)
C2—S1—C3	91.07 (14)	C9—C10—H10A	109.2
C2—C1—C8	111.3 (3)	C11—C10—H10B	109.2
C2—C1—C9	123.9 (3)	C9—C10—H10B	109.2
C8—C1—C9	124.8 (3)	H10A—C10—H10B	107.9
C1—C2—S1	114.4 (2)	N12—C11—C10	110.3 (2)
C1—C2—H2	122.8	N12—C11—H11A	109.6
S1—C2—H2	122.8	C10—C11—H11A	109.6
C4—C3—C8	122.4 (3)	N12—C11—H11B	109.6
C4—C3—S1	126.5 (2)	C10—C11—H11B	109.6
C8—C3—S1	111.0 (2)	H11A—C11—H11B	108.1
C5—C4—C3	118.5 (3)	C15—N12—C13	110.7 (2)
C5—C4—H4	120.8	C15—N12—C11	110.0 (3)
C3—C4—H4	120.8	C13—N12—C11	109.5 (2)
C4—C5—C6	120.4 (3)	N12—C13—C14	111.7 (2)
C4—C5—H5	119.8	N12—C13—H13A	109.3
C6—C5—H5	119.8	C14—C13—H13A	109.3
C7—C6—C5	121.4 (3)	N12—C13—H13B	109.3
C7—C6—H6	119.3	C14—C13—H13B	109.3
C5—C6—H6	119.3	H13A—C13—H13B	107.9
C6—C7—C8	119.3 (3)	C13—C14—C9	112.2 (2)
C6—C7—H7	120.3	C13—C14—H14A	109.2
C8—C7—H7	120.3	C9—C14—H14A	109.2
C3—C8—C7	117.9 (3)	C13—C14—H14B	109.2
C3—C8—C1	112.1 (3)	C9—C14—H14B	109.2
C7—C8—C1	129.9 (3)	H14A—C14—H14B	107.9
C16—C9—C1	109.1 (2)	N12—C15—H15A	109.5
C16—C9—C10	108.0 (2)	N12—C15—H15B	109.5
C1—C9—C10	111.5 (2)	H15A—C15—H15B	109.5
C16—C9—C14	108.4 (2)	N12—C15—H15C	109.5
C1—C9—C14	111.3 (2)	H15A—C15—H15C	109.5
C10—C9—C14	108.3 (2)	H15B—C15—H15C	109.5
C11—C10—C9	112.1 (2)	N16—C16—C9	179.1 (3)
C11—C10—H10A	109.2
C8—C1—C2—S1	0.5 (3)	C9—C1—C8—C7	−4.3 (4)
C9—C1—C2—S1	−178.8 (2)	C2—C1—C9—C16	−123.5 (3)
C3—S1—C2—C1	0.1 (2)	C8—C1—C9—C16	57.3 (3)
C2—S1—C3—C4	−179.4 (3)	C2—C1—C9—C10	−4.3 (4)
C2—S1—C3—C8	−0.7 (2)	C8—C1—C9—C10	176.6 (2)
C8—C3—C4—C5	−1.1 (4)	C2—C1—C9—C14	116.8 (3)
S1—C3—C4—C5	177.5 (2)	C8—C1—C9—C14	−62.3 (3)
C3—C4—C5—C6	−0.8 (4)	C16—C9—C10—C11	−65.9 (3)
C4—C5—C6—C7	1.8 (4)	C1—C9—C10—C11	174.2 (2)
C5—C6—C7—C8	−0.7 (4)	C14—C9—C10—C11	51.4 (3)
C4—C3—C8—C7	2.1 (4)	C9—C10—C11—N12	−58.8 (3)
S1—C3—C8—C7	−176.70 (19)	C10—C11—N12—C15	−175.9 (2)
C4—C3—C8—C1	179.9 (3)	C10—C11—N12—C13	62.2 (3)
S1—C3—C8—C1	1.1 (3)	C15—N12—C13—C14	177.1 (2)
C6—C7—C8—C3	−1.1 (4)	C11—N12—C13—C14	−61.4 (3)
C6—C7—C8—C1	−178.5 (3)	N12—C13—C14—C9	56.2 (3)
C2—C1—C8—C3	−1.0 (3)	C16—C9—C14—C13	67.2 (3)
C9—C1—C8—C3	178.2 (3)	C1—C9—C14—C13	−172.8 (2)
C2—C1—C8—C7	176.4 (3)	C10—C9—C14—C13	−49.8 (3)