2-Phenyl-N-(2-pyridylmeth­yl)acetamide

The geometrical parameters for the title compound, C₁₄H₁₄N₂O, are normal. There are two mol­ecules in the asymmetic unit. The mol­ecules assemble via N—H...O hydrogen bonds into one-dimensional chains.

Key indicators

• Single-crystal X-ray study
• T = 97 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.033
• wR factor = 0.089
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT063_ALERT_3_B Crystal Probably too Large for Beam Size .......       0.81 mm

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         10

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   2 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2002); software used to prepare material for publication: SHELXTL.

2-phenyl-N-(2-pyridylmethyl)acetamide

Crystal data

C14H14N2O	F(000) = 960
Mr = 226.27	Dx = 1.273 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7260 reflections
a = 13.414 (2) Å	θ = 2.4–28.2°
b = 9.2478 (14) Å	µ = 0.08 mm^−1
c = 19.280 (3) Å	T = 97 K
β = 99.106 (5)°	Block, colorless
V = 2361.5 (6) Å^3	0.81 × 0.41 × 0.40 mm
Z = 8

Data collection

Bruker APEX CCD diffractometer	4628 independent reflections
Radiation source: fine-focus sealed tube	4394 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan SADABS (Sheldrick, 2002)	h = −16→16
Tmin = 0.937, Tmax = 0.968	k = −11→11
24749 measured reflections	l = −23→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: difmap and geom
wR(F^2) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.047P)^2 + 0.8P] where P = (Fo^2 + 2Fc^2)/3
4628 reflections	(Δ/σ)max = 0.001
313 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

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
O1A	0.41046 (5)	0.19066 (8)	0.49858 (4)	0.02455 (17)
N1A	0.09065 (7)	0.33296 (10)	0.40327 (5)	0.0247 (2)
N2A	0.35481 (6)	0.25774 (9)	0.38664 (4)	0.01997 (18)
H2A	0.3648 (9)	0.2579 (13)	0.3419 (7)	0.024*
C1A	0.00369 (8)	0.26396 (13)	0.40589 (6)	0.0292 (2)
H1A	−0.0556	0.3206	0.4050	0.035*
C2A	−0.00522 (9)	0.11539 (14)	0.40986 (6)	0.0338 (3)
H2A1	−0.0687	0.0712	0.4116	0.041*
C3A	0.08101 (9)	0.03299 (13)	0.41116 (7)	0.0341 (3)
H3A	0.0779	−0.0694	0.4138	0.041*
C4A	0.17199 (8)	0.10205 (12)	0.40855 (6)	0.0267 (2)
H4A	0.2322	0.0476	0.4094	0.032*
C5A	0.17388 (7)	0.25170 (11)	0.40471 (5)	0.0202 (2)
C6A	0.26974 (7)	0.33835 (11)	0.40475 (5)	0.0211 (2)
H6A1	0.2548	0.4194	0.3711	0.025*
H6A2	0.2897	0.3808	0.4521	0.025*
C7A	0.42158 (7)	0.19393 (10)	0.43619 (5)	0.0191 (2)
C8A	0.51323 (7)	0.12599 (11)	0.41186 (5)	0.0205 (2)
H8A1	0.5209	0.0250	0.4288	0.025*
H8A2	0.5035	0.1244	0.3599	0.025*
C9A	0.60759 (7)	0.21078 (10)	0.43959 (5)	0.0196 (2)
C10A	0.65429 (8)	0.19666 (12)	0.50905 (6)	0.0243 (2)
H10A	0.6275	0.1314	0.5394	0.029*
C11A	0.73967 (8)	0.27696 (12)	0.53436 (6)	0.0276 (2)
H11A	0.7711	0.2663	0.5818	0.033*
C12A	0.77918 (8)	0.37277 (12)	0.49047 (6)	0.0282 (2)
H12A	0.8376	0.4280	0.5077	0.034*
C13A	0.73305 (8)	0.38747 (12)	0.42146 (6)	0.0298 (2)
H13A	0.7599	0.4531	0.3913	0.036*
C14A	0.64779 (8)	0.30693 (12)	0.39598 (6)	0.0251 (2)
H14A	0.6167	0.3176	0.3484	0.030*
O1B	0.40684 (6)	0.23413 (9)	0.24750 (4)	0.02860 (18)
N1B	0.71458 (6)	0.11980 (9)	0.21749 (4)	0.02299 (19)
N2B	0.45353 (6)	0.21462 (10)	0.14074 (5)	0.02155 (19)
H2B	0.4425 (10)	0.2386 (14)	0.0956 (7)	0.026*
C1B	0.80120 (8)	0.18496 (12)	0.24404 (6)	0.0263 (2)
H1B	0.8582	0.1258	0.2597	0.032*
C2B	0.81281 (8)	0.33329 (12)	0.25005 (6)	0.0274 (2)
H2B1	0.8764	0.3748	0.2681	0.033*
C3B	0.72921 (8)	0.41951 (12)	0.22896 (5)	0.0258 (2)
H3B	0.7339	0.5217	0.2330	0.031*
C4B	0.63845 (8)	0.35400 (11)	0.20188 (5)	0.0229 (2)
H4B	0.5798	0.4108	0.1874	0.027*
C5B	0.63425 (7)	0.20438 (11)	0.19615 (5)	0.0199 (2)
C6B	0.53961 (7)	0.12282 (11)	0.16506 (5)	0.0234 (2)
H6B1	0.5546	0.0639	0.1251	0.028*
H6B2	0.5213	0.0556	0.2010	0.028*
C7B	0.39365 (7)	0.26525 (11)	0.18448 (5)	0.0207 (2)
C8B	0.30853 (7)	0.36495 (11)	0.15184 (5)	0.0226 (2)
H8B1	0.3124	0.4570	0.1784	0.027*
H8B2	0.3166	0.3873	0.1028	0.027*
C9B	0.20639 (7)	0.29570 (10)	0.15253 (5)	0.0200 (2)
C10B	0.15460 (8)	0.23117 (12)	0.09212 (5)	0.0247 (2)
H10B	0.1818	0.2356	0.0496	0.030*
C11B	0.06378 (8)	0.16053 (12)	0.09346 (6)	0.0278 (2)
H11B	0.0293	0.1167	0.0519	0.033*
C12B	0.02290 (8)	0.15338 (12)	0.15501 (6)	0.0270 (2)
H12B	−0.0387	0.1034	0.1561	0.032*
C13B	0.07293 (8)	0.22003 (12)	0.21520 (6)	0.0263 (2)
H13B	0.0449	0.2170	0.2574	0.032*
C14B	0.16385 (8)	0.29112 (11)	0.21380 (5)	0.0231 (2)
H14B	0.1973	0.3371	0.2551	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0264 (4)	0.0307 (4)	0.0164 (4)	0.0002 (3)	0.0029 (3)	0.0009 (3)
N1A	0.0220 (4)	0.0285 (5)	0.0228 (4)	0.0038 (4)	0.0013 (3)	−0.0007 (4)
N2A	0.0207 (4)	0.0234 (4)	0.0162 (4)	0.0000 (3)	0.0039 (3)	0.0006 (3)
C1A	0.0211 (5)	0.0403 (6)	0.0258 (5)	0.0028 (5)	0.0026 (4)	−0.0021 (5)
C2A	0.0247 (5)	0.0428 (7)	0.0340 (6)	−0.0088 (5)	0.0054 (5)	−0.0013 (5)
C3A	0.0348 (6)	0.0266 (6)	0.0415 (7)	−0.0062 (5)	0.0077 (5)	−0.0007 (5)
C4A	0.0256 (5)	0.0241 (5)	0.0309 (5)	0.0012 (4)	0.0062 (4)	−0.0008 (4)
C5A	0.0221 (5)	0.0243 (5)	0.0140 (4)	0.0013 (4)	0.0021 (4)	−0.0005 (4)
C6A	0.0225 (5)	0.0195 (5)	0.0210 (5)	0.0011 (4)	0.0031 (4)	−0.0002 (4)
C7A	0.0206 (5)	0.0174 (4)	0.0190 (5)	−0.0045 (4)	0.0019 (4)	−0.0008 (4)
C8A	0.0215 (5)	0.0198 (5)	0.0196 (5)	−0.0006 (4)	0.0018 (4)	−0.0014 (4)
C9A	0.0185 (5)	0.0184 (5)	0.0222 (5)	0.0024 (4)	0.0039 (4)	−0.0026 (4)
C10A	0.0240 (5)	0.0250 (5)	0.0234 (5)	0.0002 (4)	0.0022 (4)	0.0013 (4)
C11A	0.0234 (5)	0.0323 (6)	0.0254 (5)	0.0019 (4)	−0.0014 (4)	−0.0052 (4)
C12A	0.0193 (5)	0.0288 (6)	0.0369 (6)	−0.0030 (4)	0.0055 (4)	−0.0116 (5)
C13A	0.0293 (6)	0.0289 (6)	0.0333 (6)	−0.0069 (5)	0.0116 (5)	−0.0025 (5)
C14A	0.0265 (5)	0.0273 (5)	0.0218 (5)	−0.0016 (4)	0.0044 (4)	−0.0003 (4)
O1B	0.0273 (4)	0.0407 (5)	0.0183 (4)	0.0040 (3)	0.0052 (3)	0.0042 (3)
N1B	0.0231 (4)	0.0228 (4)	0.0230 (4)	0.0031 (3)	0.0035 (3)	0.0015 (3)
N2B	0.0208 (4)	0.0266 (5)	0.0170 (4)	0.0026 (3)	0.0024 (3)	0.0016 (3)
C1B	0.0214 (5)	0.0295 (6)	0.0275 (5)	0.0039 (4)	0.0023 (4)	0.0029 (4)
C2B	0.0236 (5)	0.0309 (6)	0.0271 (5)	−0.0044 (4)	0.0024 (4)	0.0002 (4)
C3B	0.0316 (6)	0.0216 (5)	0.0248 (5)	−0.0018 (4)	0.0059 (4)	0.0015 (4)
C4B	0.0246 (5)	0.0225 (5)	0.0217 (5)	0.0032 (4)	0.0040 (4)	0.0033 (4)
C5B	0.0217 (5)	0.0229 (5)	0.0158 (5)	0.0021 (4)	0.0050 (4)	0.0020 (4)
C6B	0.0227 (5)	0.0224 (5)	0.0250 (5)	0.0019 (4)	0.0035 (4)	−0.0002 (4)
C7B	0.0197 (5)	0.0235 (5)	0.0188 (5)	−0.0033 (4)	0.0026 (4)	0.0001 (4)
C8B	0.0226 (5)	0.0225 (5)	0.0230 (5)	0.0013 (4)	0.0046 (4)	0.0020 (4)
C9B	0.0199 (5)	0.0180 (5)	0.0216 (5)	0.0044 (4)	0.0017 (4)	0.0018 (4)
C10B	0.0274 (5)	0.0271 (5)	0.0196 (5)	0.0049 (4)	0.0031 (4)	−0.0014 (4)
C11B	0.0266 (5)	0.0277 (6)	0.0266 (5)	0.0021 (4)	−0.0033 (4)	−0.0065 (4)
C12B	0.0204 (5)	0.0253 (5)	0.0344 (6)	0.0002 (4)	0.0014 (4)	0.0001 (4)
C13B	0.0227 (5)	0.0325 (6)	0.0243 (5)	0.0019 (4)	0.0057 (4)	0.0017 (4)
C14B	0.0225 (5)	0.0261 (5)	0.0199 (5)	0.0015 (4)	0.0010 (4)	−0.0016 (4)

Geometric parameters (Å, º)

O1A—C7A	1.2357 (12)	O1B—C7B	1.2339 (13)
N1A—C1A	1.3376 (15)	N1B—C1B	1.3367 (14)
N1A—C5A	1.3424 (13)	N1B—C5B	1.3424 (13)
N2A—C7A	1.3387 (13)	N2B—C7B	1.3379 (13)
N2A—C6A	1.4512 (13)	N2B—C6B	1.4500 (13)
N2A—H2A	0.893 (13)	N2B—H2B	0.888 (14)
C1A—C2A	1.3823 (18)	C1B—C2B	1.3833 (16)
C1A—H1A	0.9500	C1B—H1B	0.9500
C2A—C3A	1.3820 (17)	C2B—C3B	1.3836 (16)
C2A—H2A1	0.9500	C2B—H2B1	0.9500
C3A—C4A	1.3852 (15)	C3B—C4B	1.3858 (15)
C3A—H3A	0.9500	C3B—H3B	0.9500
C4A—C5A	1.3864 (15)	C4B—C5B	1.3886 (15)
C4A—H4A	0.9500	C4B—H4B	0.9500
C5A—C6A	1.5150 (14)	C5B—C6B	1.5162 (14)
C6A—H6A1	0.9900	C6B—H6B1	0.9900
C6A—H6A2	0.9900	C6B—H6B2	0.9900
C7A—C8A	1.5194 (14)	C7B—C8B	1.5240 (14)
C8A—C9A	1.5129 (13)	C8B—C9B	1.5144 (14)
C8A—H8A1	0.9900	C8B—H8B1	0.9900
C8A—H8A2	0.9900	C8B—H8B2	0.9900
C9A—C14A	1.3899 (15)	C9B—C14B	1.3915 (15)
C9A—C10A	1.3919 (15)	C9B—C10B	1.3925 (15)
C10A—C11A	1.3873 (15)	C10B—C11B	1.3862 (16)
C10A—H10A	0.9500	C10B—H10B	0.9500
C11A—C12A	1.3871 (17)	C11B—C12B	1.3855 (16)
C11A—H11A	0.9500	C11B—H11B	0.9500
C12A—C13A	1.3825 (17)	C12B—C13B	1.3894 (16)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—C14A	1.3878 (15)	C13B—C14B	1.3894 (15)
C13A—H13A	0.9500	C13B—H13B	0.9500
C14A—H14A	0.9500	C14B—H14B	0.9500
C1A—N1A—C5A	117.36 (10)	C1B—N1B—C5B	117.49 (9)
C7A—N2A—C6A	121.16 (9)	C7B—N2B—C6B	121.86 (9)
C7A—N2A—H2A	120.3 (8)	C7B—N2B—H2B	120.5 (8)
C6A—N2A—H2A	118.4 (8)	C6B—N2B—H2B	117.6 (8)
N1A—C1A—C2A	124.04 (11)	N1B—C1B—C2B	123.96 (10)
N1A—C1A—H1A	118.0	N1B—C1B—H1B	118.0
C2A—C1A—H1A	118.0	C2B—C1B—H1B	118.0
C3A—C2A—C1A	118.01 (11)	C1B—C2B—C3B	118.13 (10)
C3A—C2A—H2A1	121.0	C1B—C2B—H2B1	120.9
C1A—C2A—H2A1	121.0	C3B—C2B—H2B1	120.9
C2A—C3A—C4A	119.00 (11)	C2B—C3B—C4B	118.79 (10)
C2A—C3A—H3A	120.5	C2B—C3B—H3B	120.6
C4A—C3A—H3A	120.5	C4B—C3B—H3B	120.6
C3A—C4A—C5A	119.07 (10)	C3B—C4B—C5B	119.19 (10)
C3A—C4A—H4A	120.5	C3B—C4B—H4B	120.4
C5A—C4A—H4A	120.5	C5B—C4B—H4B	120.4
N1A—C5A—C4A	122.52 (10)	N1B—C5B—C4B	122.39 (9)
N1A—C5A—C6A	114.01 (9)	N1B—C5B—C6B	114.37 (9)
C4A—C5A—C6A	123.42 (9)	C4B—C5B—C6B	123.24 (9)
N2A—C6A—C5A	115.33 (8)	N2B—C6B—C5B	114.24 (9)
N2A—C6A—H6A1	108.4	N2B—C6B—H6B1	108.7
C5A—C6A—H6A1	108.4	C5B—C6B—H6B1	108.7
N2A—C6A—H6A2	108.4	N2B—C6B—H6B2	108.7
C5A—C6A—H6A2	108.4	C5B—C6B—H6B2	108.7
H6A1—C6A—H6A2	107.5	H6B1—C6B—H6B2	107.6
O1A—C7A—N2A	122.36 (9)	O1B—C7B—N2B	122.16 (10)
O1A—C7A—C8A	121.24 (9)	O1B—C7B—C8B	121.95 (9)
N2A—C7A—C8A	116.40 (9)	N2B—C7B—C8B	115.89 (9)
C9A—C8A—C7A	110.44 (8)	C9B—C8B—C7B	111.11 (8)
C9A—C8A—H8A1	109.6	C9B—C8B—H8B1	109.4
C7A—C8A—H8A1	109.6	C7B—C8B—H8B1	109.4
C9A—C8A—H8A2	109.6	C9B—C8B—H8B2	109.4
C7A—C8A—H8A2	109.6	C7B—C8B—H8B2	109.4
H8A1—C8A—H8A2	108.1	H8B1—C8B—H8B2	108.0
C14A—C9A—C10A	118.91 (9)	C14B—C9B—C10B	118.67 (10)
C14A—C9A—C8A	120.05 (9)	C14B—C9B—C8B	120.90 (9)
C10A—C9A—C8A	121.03 (9)	C10B—C9B—C8B	120.40 (9)
C11A—C10A—C9A	120.60 (10)	C11B—C10B—C9B	120.66 (10)
C11A—C10A—H10A	119.7	C11B—C10B—H10B	119.7
C9A—C10A—H10A	119.7	C9B—C10B—H10B	119.7
C12A—C11A—C10A	120.08 (10)	C12B—C11B—C10B	120.44 (10)
C12A—C11A—H11A	120.0	C12B—C11B—H11B	119.8
C10A—C11A—H11A	120.0	C10B—C11B—H11B	119.8
C13A—C12A—C11A	119.60 (10)	C11B—C12B—C13B	119.33 (10)
C13A—C12A—H12A	120.2	C11B—C12B—H12B	120.3
C11A—C12A—H12A	120.2	C13B—C12B—H12B	120.3
C12A—C13A—C14A	120.40 (10)	C14B—C13B—C12B	120.20 (10)
C12A—C13A—H13A	119.8	C14B—C13B—H13B	119.9
C14A—C13A—H13A	119.8	C12B—C13B—H13B	119.9
C13A—C14A—C9A	120.41 (10)	C13B—C14B—C9B	120.67 (10)
C13A—C14A—H14A	119.8	C13B—C14B—H14B	119.7
C9A—C14A—H14A	119.8	C9B—C14B—H14B	119.7
C5A—N1A—C1A—C2A	−0.08 (16)	C5B—N1B—C1B—C2B	−0.66 (16)
N1A—C1A—C2A—C3A	−0.03 (18)	N1B—C1B—C2B—C3B	1.68 (17)
C1A—C2A—C3A—C4A	0.07 (18)	C1B—C2B—C3B—C4B	−1.01 (15)
C2A—C3A—C4A—C5A	0.00 (17)	C2B—C3B—C4B—C5B	−0.53 (15)
C1A—N1A—C5A—C4A	0.16 (15)	C1B—N1B—C5B—C4B	−1.02 (14)
C1A—N1A—C5A—C6A	−177.48 (9)	C1B—N1B—C5B—C6B	178.57 (9)
C3A—C4A—C5A—N1A	−0.12 (16)	C3B—C4B—C5B—N1B	1.62 (15)
C3A—C4A—C5A—C6A	177.29 (10)	C3B—C4B—C5B—C6B	−177.94 (9)
C7A—N2A—C6A—C5A	−91.32 (11)	C7B—N2B—C6B—C5B	−83.22 (12)
N1A—C5A—C6A—N2A	−163.48 (8)	N1B—C5B—C6B—N2B	−178.80 (8)
C4A—C5A—C6A—N2A	18.90 (14)	C4B—C5B—C6B—N2B	0.79 (14)
C6A—N2A—C7A—O1A	5.63 (14)	C6B—N2B—C7B—O1B	−1.69 (15)
C6A—N2A—C7A—C8A	−173.87 (8)	C6B—N2B—C7B—C8B	177.80 (9)
O1A—C7A—C8A—C9A	−68.83 (12)	O1B—C7B—C8B—C9B	−67.02 (13)
N2A—C7A—C8A—C9A	110.68 (10)	N2B—C7B—C8B—C9B	113.49 (10)
C7A—C8A—C9A—C14A	−101.21 (11)	C7B—C8B—C9B—C14B	77.53 (12)
C7A—C8A—C9A—C10A	77.39 (12)	C7B—C8B—C9B—C10B	−100.44 (11)
C14A—C9A—C10A—C11A	−0.13 (15)	C14B—C9B—C10B—C11B	−1.66 (15)
C8A—C9A—C10A—C11A	−178.74 (9)	C8B—C9B—C10B—C11B	176.35 (9)
C9A—C10A—C11A—C12A	0.20 (16)	C9B—C10B—C11B—C12B	0.18 (16)
C10A—C11A—C12A—C13A	−0.09 (16)	C10B—C11B—C12B—C13B	1.16 (16)
C11A—C12A—C13A—C14A	−0.09 (17)	C11B—C12B—C13B—C14B	−1.01 (16)
C12A—C13A—C14A—C9A	0.16 (17)	C12B—C13B—C14B—C9B	−0.49 (16)
C10A—C9A—C14A—C13A	−0.05 (15)	C10B—C9B—C14B—C13B	1.81 (15)
C8A—C9A—C14A—C13A	178.58 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2A···O1B	0.893 (13)	2.001 (14)	2.8850 (12)	170.0 (11)
N2B—H2B···O1A^i	0.888 (14)	1.964 (14)	2.8483 (12)	174.0 (12)

Symmetry code: (i) x, −y+1/2, z−1/2.