3-[2-(3-Chloro­phenyl)­ethyl]­pyridine-2-carbo­nitrile

Li, X.-P.; Chen, H.-Y.; Wang, X.-M.; Zhou, C.-X.; Zhao, Y.

doi:10.1107/S1600536805013681

3-[2-(3-Chlorophenyl)ethyl]pyridine-2-carbonitrile

X.-P. Li, H.-Y. Chen, X.-M. Wang, C.-X. Zhou and Y. Zhao

The title compound, C₁₄H₁₁ClN₂, is the key intermediate in the synthesis of the antihistaminic drug loratadine. The benzene and pyridine rings are connected through the ethylene bridge and are coplanar. There are intermolecular π–π and C—Cl

N interactions and weak hydrogen bonds stabilizing the packing.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805013681/er6014sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805013681/er6014Isup2.hkl Contains datablock I

CCDC reference: 274392

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.048
wR factor = 0.127
Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.598     0.939
            Tmin' and Tmax expected:      0.860     0.939
            RR' =      0.695
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.69

Alert level C
PLAT127_ALERT_1_C Implicit Hall Symbol  Inconsistent with Explicit     P -2yn
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C5     -   C6     ...       1.45 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl     ..  N1      ..       3.28 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         12
            N1  -C5  -C6  -N2   -177.00100.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         13
            C4  -C5  -C6  -N2      3.00  5.00   1.555   1.555   1.555   1.555

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL.

3-[2-(3-Chlorophenyl)ethyl]pyridine-2-carbonitrile top

Crystal data top

C₁₄H₁₁ClN₂	F(000) = 504
M_r = 242.70	D_x = 1.318 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yn	Cell parameters from 2106 reflections
a = 7.5645 (8) Å	θ = 5.7–52.8°
b = 12.2332 (12) Å	µ = 0.29 mm⁻¹
c = 13.5558 (14) Å	T = 293 K
β = 102.867 (2)°	Prism, colorless
V = 1222.9 (2) Å³	0.51 × 0.39 × 0.22 mm
Z = 4

Data collection top

Brruker SMART 1K CCD area-detector diffractometer	2668 independent reflections
Radiation source: fine-focus sealed tube	1924 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
Detector resolution: 10 pixels mm^-1	θ_max = 27.0°, θ_min = 2.3°
φ and ω scans to fill Ewald sphere	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	k = −10→15
T_min = 0.598, T_max = 0.939	l = −17→17
7051 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	All H-atom parameters refined
S = 1.01	w = 1/[σ²(F_o²) + (0.0674P)²] where P = (F_o² + 2F_c²)/3
2668 reflections	(Δ/σ)_max = 0.001
198 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl	1.04722 (7)	0.62645 (5)	0.83201 (4)	0.0655 (2)
N1	−0.1352 (2)	0.90726 (14)	0.53814 (12)	0.0504 (4)
N2	0.0153 (3)	0.71100 (17)	0.40003 (14)	0.0718 (6)
C1	−0.1391 (3)	0.97120 (17)	0.61681 (18)	0.0557 (5)
C2	−0.0138 (3)	0.96808 (17)	0.70605 (19)	0.0576 (6)
C3	0.1268 (3)	0.89547 (17)	0.71739 (16)	0.0499 (5)
C4	0.1399 (2)	0.82676 (14)	0.63801 (13)	0.0377 (4)
C5	0.0044 (2)	0.83719 (14)	0.55141 (13)	0.0392 (4)
C6	0.0074 (3)	0.76763 (17)	0.46554 (14)	0.0485 (5)
C7	0.2935 (2)	0.74683 (15)	0.64606 (15)	0.0417 (4)
C8	0.4575 (3)	0.79654 (18)	0.6144 (2)	0.0545 (5)
C9	0.6095 (2)	0.71521 (15)	0.62397 (14)	0.0450 (5)
C10	0.6149 (3)	0.64171 (18)	0.54665 (18)	0.0559 (5)
C11	0.7517 (3)	0.56415 (19)	0.55825 (19)	0.0641 (6)
C12	0.8838 (3)	0.55908 (18)	0.64501 (18)	0.0570 (6)
C13	0.8790 (2)	0.63229 (15)	0.72087 (16)	0.0465 (5)
C14	0.7429 (2)	0.70954 (15)	0.71113 (15)	0.0442 (4)
H1	−0.235 (3)	1.0181 (17)	0.6090 (15)	0.058 (6)*
H2	−0.021 (3)	1.0144 (19)	0.7614 (16)	0.068 (6)*
H3	0.205 (3)	0.8886 (15)	0.7772 (16)	0.051 (6)*
H6	0.325 (3)	0.7213 (17)	0.7154 (16)	0.065 (6)*
H7	0.246 (3)	0.6795 (17)	0.6015 (14)	0.050 (5)*
H8	0.495 (3)	0.8646 (19)	0.6547 (17)	0.068 (7)*
H9	0.422 (3)	0.821 (2)	0.5466 (18)	0.077 (7)*
H10	0.534 (3)	0.6416 (15)	0.4868 (15)	0.049 (6)*
H11	0.750 (3)	0.515 (2)	0.5047 (18)	0.083 (8)*
H12	0.977 (3)	0.5089 (18)	0.6524 (15)	0.066 (6)*
H14	0.745 (3)	0.7602 (16)	0.7646 (13)	0.045 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0432 (3)	0.0772 (4)	0.0730 (4)	−0.0040 (2)	0.0066 (3)	0.0147 (3)
N1	0.0390 (9)	0.0495 (10)	0.0632 (10)	0.0076 (7)	0.0128 (8)	0.0094 (8)
N2	0.0815 (15)	0.0797 (14)	0.0536 (11)	0.0064 (11)	0.0137 (10)	−0.0098 (10)
C1	0.0447 (12)	0.0424 (12)	0.0858 (16)	0.0097 (9)	0.0265 (11)	0.0039 (11)
C2	0.0551 (13)	0.0460 (12)	0.0770 (15)	−0.0028 (9)	0.0259 (11)	−0.0178 (11)
C3	0.0434 (11)	0.0525 (12)	0.0531 (12)	−0.0048 (9)	0.0090 (9)	−0.0101 (9)
C4	0.0315 (8)	0.0343 (9)	0.0489 (10)	−0.0026 (7)	0.0124 (7)	0.0013 (7)
C5	0.0344 (9)	0.0378 (10)	0.0472 (10)	−0.0008 (7)	0.0128 (8)	0.0037 (8)
C6	0.0454 (11)	0.0547 (12)	0.0438 (10)	0.0040 (9)	0.0067 (8)	0.0039 (9)
C7	0.0337 (9)	0.0408 (11)	0.0509 (11)	0.0033 (8)	0.0100 (8)	0.0050 (9)
C8	0.0394 (11)	0.0449 (12)	0.0832 (16)	0.0061 (8)	0.0222 (10)	0.0151 (11)
C9	0.0342 (9)	0.0380 (10)	0.0676 (12)	−0.0009 (7)	0.0213 (9)	0.0080 (9)
C10	0.0435 (12)	0.0602 (14)	0.0627 (14)	−0.0023 (9)	0.0090 (10)	−0.0015 (10)
C11	0.0617 (15)	0.0548 (14)	0.0798 (16)	−0.0011 (11)	0.0243 (13)	−0.0183 (12)
C12	0.0431 (11)	0.0457 (12)	0.0857 (16)	0.0070 (9)	0.0220 (11)	0.0007 (11)
C13	0.0334 (9)	0.0447 (11)	0.0637 (12)	−0.0045 (8)	0.0162 (9)	0.0065 (9)
C14	0.0384 (10)	0.0398 (11)	0.0593 (11)	−0.0045 (8)	0.0215 (9)	0.0009 (9)

Geometric parameters (Å, º) top

Cl—C13	1.743 (2)	C7—H7	1.04 (2)
N1—C1	1.328 (3)	C8—C9	1.504 (3)
N1—C5	1.341 (2)	C8—H8	1.00 (2)
N2—C6	1.138 (2)	C8—H9	0.95 (2)
C1—C2	1.361 (3)	C9—C14	1.374 (3)
C1—H1	0.91 (2)	C9—C10	1.388 (3)
C2—C3	1.368 (3)	C10—C11	1.387 (3)
C2—H2	0.95 (2)	C10—H10	0.90 (2)
C3—C4	1.386 (3)	C11—C12	1.365 (3)
C3—H3	0.89 (2)	C11—H11	0.94 (3)
C4—C5	1.382 (2)	C12—C13	1.370 (3)
C4—C7	1.504 (2)	C12—H12	0.92 (2)
C5—C6	1.446 (3)	C13—C14	1.382 (3)
C7—C8	1.526 (3)	C14—H14	0.950 (19)
C7—H6	0.97 (2)

C1—N1—C5	115.24 (17)	C9—C8—H8	112.7 (14)
N1—C1—C2	124.17 (19)	C7—C8—H8	109.1 (14)
N1—C1—H1	115.9 (13)	C9—C8—H9	109.8 (15)
C2—C1—H1	119.9 (13)	C7—C8—H9	108.9 (16)
C1—C2—C3	119.2 (2)	H8—C8—H9	104.6 (19)
C1—C2—H2	122.1 (14)	C14—C9—C10	118.50 (18)
C3—C2—H2	118.6 (14)	C14—C9—C8	120.54 (19)
C2—C3—C4	119.7 (2)	C10—C9—C8	120.9 (2)
C2—C3—H3	120.1 (13)	C11—C10—C9	120.3 (2)
C4—C3—H3	120.0 (13)	C11—C10—H10	116.1 (12)
C5—C4—C3	115.82 (17)	C9—C10—H10	123.7 (12)
C5—C4—C7	122.46 (16)	C12—C11—C10	120.9 (2)
C3—C4—C7	121.72 (17)	C12—C11—H11	121.4 (16)
N1—C5—C4	125.88 (17)	C10—C11—H11	117.7 (16)
N1—C5—C6	114.91 (16)	C11—C12—C13	118.7 (2)
C4—C5—C6	119.21 (15)	C11—C12—H12	121.2 (13)
N2—C6—C5	177.5 (2)	C13—C12—H12	120.1 (14)
C4—C7—C8	112.56 (15)	C12—C13—C14	121.2 (2)
C4—C7—H6	107.4 (13)	C12—C13—Cl	119.06 (15)
C8—C7—H6	111.2 (13)	C14—C13—Cl	119.70 (16)
C4—C7—H7	108.3 (11)	C9—C14—C13	120.37 (19)
C8—C7—H7	110.5 (10)	C9—C14—H14	120.6 (11)
H6—C7—H7	106.7 (16)	C13—C14—H14	119.0 (11)
C9—C8—C7	111.46 (16)

C5—N1—C1—C2	−0.4 (3)	C3—C4—C7—C8	−88.4 (2)
N1—C1—C2—C3	0.2 (3)	C4—C7—C8—C9	179.56 (18)
C1—C2—C3—C4	0.3 (3)	C7—C8—C9—C14	−92.8 (2)
C2—C3—C4—C5	−0.5 (3)	C7—C8—C9—C10	84.9 (2)
C2—C3—C4—C7	178.98 (18)	C14—C9—C10—C11	0.5 (3)
C1—N1—C5—C4	0.1 (3)	C8—C9—C10—C11	−177.25 (19)
C1—N1—C5—C6	179.82 (16)	C9—C10—C11—C12	−0.6 (3)
C3—C4—C5—N1	0.3 (3)	C10—C11—C12—C13	0.0 (3)
C7—C4—C5—N1	−179.15 (17)	C11—C12—C13—C14	0.6 (3)
C3—C4—C5—C6	−179.37 (16)	C11—C12—C13—Cl	179.99 (16)
C7—C4—C5—C6	1.1 (2)	C10—C9—C14—C13	0.1 (3)
N1—C5—C6—N2	−177 (100)	C8—C9—C14—C13	177.88 (16)
C4—C5—C6—N2	3 (5)	C12—C13—C14—C9	−0.7 (3)
C5—C4—C7—C8	91.0 (2)	Cl—C13—C14—C9	179.93 (13)

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3-[2-(3-Chloro­phenyl)­ethyl]­pyridine-2-carbo­nitrile

Supporting information

Key indicators

checkCIF/PLATON results

3-[2-(3-Chlorophenyl)ethyl]pyridine-2-carbonitrile