N-(3-Pyridylmethyl)salicylamide

In the title compound, C₁₃H₁₂N₂O₂, all bond lengths and angles are within normal ranges. N—H...N and C—H...N hydrogen bonding, with N...N = 2.986 (2) Å, C...N = 3.453 (2) Å, N—H...N = 160° and C—H...N = 158°, links mol­ecules into supra­molecular chains in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.047
• wR factor = 0.128
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level A
REFI021_ALERT_1_A  _refine_ls_abs_structure_details is missing
            Absolute structure method and Friedel-pair number.
            This should be present as the _refine_ls_abs_structure_Flack or Roge
            field has been filled out.

Alert level B
STRDE01_ALERT_1_B  A value for _refine_ls_abs_structure_flack has been given,
            without an explanantion in the _refine_ls_abs_structure_details
            field.

Alert level G
PLAT033_ALERT_2_G Flack Parameter Value Deviates 2 * su from zero.       0.06

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Related literature

For related literature, see: Zhang et al. (2002).

S1. Experimental

A mixture of methyl salicylate (1 mmol, 0.152 g) and 3-(aminomethyl)pyridine (1 mmol, 0.108 g) was reflux at 120 °C in 25 ml CHCl₃ solution for 5 h. This resulting solution was cooled and the pale yellow crystals formed. Yield: 60%, m.p.172. Anal. Calcd. for C₁₃H₁₂N₂O₂: C, 68.41; H, 5.30; N, 12.27; Found: C, 68.24; H, 5.23; N, 12.11%.

S2. Refinement

H2A and H2B atoms were initially located in difference Fourier map, and were subsequently included in the refinement in calculated positions ans treated as riding atom. All atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms (C—H = 0.93, 0.97 Å; N—H = 0.86 Å; O—H = 0.82 Å) and U_iso(H) values weren taken to be equal to 1.2 U_eq(C, N) and 1.5Ueq(O).

Structure description

For related literature, see: Zhang et al. (2002).

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Figures

Fig. 1. The structure of (I) showing 30% probability displacement ellipsoids and the atom-numbering scheme.

N-(3-Pyridylmethyl)salicylamide

Crystal data

C13H12N2O2	Dx = 1.355 Mg m^−3
Mr = 228.25	Melting point: 172 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 12.218 (2) Å	θ = 1.0–27.5°
b = 10.928 (2) Å	µ = 0.09 mm^−1
c = 16.757 (3) Å	T = 295 K
V = 2237.4 (7) Å^3	Block, yellow
Z = 8	0.58 × 0.56 × 0.52 mm
F(000) = 960

Data collection

Bruker SMART CCD diffractometer	2359 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
Graphite monochromator	θmax = 27.5°, θmin = 2.4°
phi and ω scans	h = −15→12
16054 measured reflections	k = −14→14
2557 independent reflections	l = −20→21

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.128	H-atom parameters constrained
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0642P)^2 + 0.3875P] where P = (Fo^2 + 2Fc^2)/3
2557 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.14 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
O1	0.87402 (8)	0.14006 (9)	0.31068 (7)	0.0549 (3)
N2	1.05351 (9)	0.09770 (9)	0.31664 (7)	0.0410 (3)
H2B	1.1047	0.0530	0.3365	0.049*
C8	0.92537 (10)	−0.03485 (11)	0.38595 (7)	0.0355 (3)
C5	1.10580 (10)	0.31634 (11)	0.30579 (7)	0.0369 (3)
C1	1.02288 (10)	0.38677 (12)	0.33848 (8)	0.0416 (3)
H1	0.9504	0.3615	0.3345	0.050*
C13	0.81588 (10)	−0.07066 (12)	0.39587 (8)	0.0439 (3)
C4	1.21143 (11)	0.35963 (12)	0.31291 (9)	0.0462 (3)
H4	1.2676	0.3132	0.2909	0.055*
N1	1.23798 (10)	0.46445 (11)	0.34950 (8)	0.0549 (3)
C7	0.94970 (10)	0.07362 (11)	0.33559 (8)	0.0380 (3)
C9	1.00574 (11)	−0.10440 (12)	0.42388 (8)	0.0432 (3)
H9	1.0788	−0.0816	0.4188	0.052*
O2	0.73213 (8)	−0.00715 (11)	0.36415 (8)	0.0688 (4)
H2A	0.7560	0.0527	0.3404	0.103*
C6	1.08250 (12)	0.19794 (12)	0.26310 (8)	0.0460 (3)
H6B	1.0229	0.2108	0.2258	0.055*
H6A	1.1466	0.1747	0.2326	0.055*
C3	1.15656 (13)	0.52891 (13)	0.38062 (9)	0.0532 (4)
H3	1.1735	0.6018	0.4065	0.064*
C12	0.79112 (12)	−0.17601 (14)	0.43906 (9)	0.0542 (4)
H12	0.7188	−0.2015	0.4434	0.065*
C2	1.04838 (12)	0.49411 (12)	0.37683 (9)	0.0481 (3)
H2	0.9939	0.5421	0.3997	0.058*
C10	0.97963 (13)	−0.20563 (13)	0.46849 (9)	0.0518 (4)
H10	1.0344	−0.2495	0.4943	0.062*
C11	0.87208 (14)	−0.24216 (14)	0.47500 (9)	0.0549 (4)
H11	0.8546	−0.3121	0.5040	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0385 (5)	0.0485 (6)	0.0778 (7)	0.0068 (4)	−0.0065 (5)	0.0142 (5)
N2	0.0351 (6)	0.0339 (5)	0.0541 (6)	0.0008 (4)	0.0023 (5)	0.0004 (4)
C8	0.0318 (6)	0.0348 (6)	0.0398 (6)	0.0001 (4)	−0.0002 (5)	−0.0050 (5)
C5	0.0357 (6)	0.0348 (6)	0.0403 (6)	−0.0009 (5)	0.0022 (5)	0.0049 (5)
C1	0.0308 (6)	0.0412 (6)	0.0529 (7)	0.0001 (5)	0.0010 (5)	0.0033 (5)
C13	0.0334 (6)	0.0484 (7)	0.0498 (7)	0.0006 (5)	−0.0005 (5)	−0.0017 (6)
C4	0.0322 (6)	0.0444 (7)	0.0620 (8)	0.0009 (5)	0.0045 (6)	0.0043 (6)
N1	0.0375 (6)	0.0505 (7)	0.0766 (8)	−0.0080 (5)	−0.0068 (6)	0.0022 (6)
C7	0.0344 (6)	0.0344 (6)	0.0453 (6)	0.0018 (5)	−0.0024 (5)	−0.0040 (5)
C9	0.0360 (6)	0.0432 (7)	0.0504 (7)	0.0025 (5)	−0.0027 (5)	−0.0009 (6)
O2	0.0306 (5)	0.0763 (8)	0.0994 (9)	0.0018 (5)	−0.0056 (5)	0.0242 (7)
C6	0.0490 (8)	0.0411 (6)	0.0478 (7)	−0.0038 (6)	0.0098 (6)	−0.0023 (5)
C3	0.0553 (9)	0.0398 (7)	0.0645 (9)	−0.0046 (6)	−0.0082 (7)	−0.0039 (6)
C12	0.0451 (8)	0.0580 (8)	0.0595 (8)	−0.0117 (6)	0.0065 (6)	0.0030 (7)
C2	0.0464 (8)	0.0398 (7)	0.0582 (8)	0.0060 (5)	0.0036 (6)	−0.0016 (6)
C10	0.0565 (9)	0.0472 (7)	0.0517 (8)	0.0072 (6)	−0.0058 (6)	0.0066 (6)
C11	0.0655 (9)	0.0491 (8)	0.0502 (8)	−0.0062 (7)	0.0048 (7)	0.0078 (6)

Geometric parameters (Å, º)

O1—C7	1.2474 (15)	C4—H4	0.9300
N2—C7	1.3337 (16)	N1—C3	1.326 (2)
N2—C6	1.4596 (16)	C9—C10	1.3727 (19)
N2—H2B	0.8600	C9—H9	0.9300
C8—C9	1.3950 (18)	O2—H2A	0.8200
C8—C13	1.4037 (17)	C6—H6B	0.9700
C8—C7	1.4851 (18)	C6—H6A	0.9700
C5—C4	1.3797 (18)	C3—C2	1.377 (2)
C5—C1	1.3852 (17)	C3—H3	0.9300
C5—C6	1.5057 (17)	C12—C11	1.365 (2)
C1—C2	1.373 (2)	C12—H12	0.9300
C1—H1	0.9300	C2—H2	0.9300
C13—O2	1.3459 (17)	C10—C11	1.378 (2)
C13—C12	1.393 (2)	C10—H10	0.9300
C4—N1	1.3391 (19)	C11—H11	0.9300
C7—N2—C6	121.68 (11)	C8—C9—H9	119.2
C7—N2—H2B	119.2	C13—O2—H2A	109.5
C6—N2—H2B	119.2	N2—C6—C5	113.50 (11)
C9—C8—C13	117.71 (12)	N2—C6—H6B	108.9
C9—C8—C7	123.56 (11)	C5—C6—H6B	108.9
C13—C8—C7	118.73 (11)	N2—C6—H6A	108.9
C4—C5—C1	117.35 (12)	C5—C6—H6A	108.9
C4—C5—C6	120.83 (12)	H6B—C6—H6A	107.7
C1—C5—C6	121.81 (11)	N1—C3—C2	123.73 (13)
C2—C1—C5	119.58 (12)	N1—C3—H3	118.1
C2—C1—H1	120.2	C2—C3—H3	118.1
C5—C1—H1	120.2	C11—C12—C13	120.63 (13)
O2—C13—C12	117.79 (12)	C11—C12—H12	119.7
O2—C13—C8	122.28 (12)	C13—C12—H12	119.7
C12—C13—C8	119.93 (12)	C1—C2—C3	118.38 (13)
N1—C4—C5	124.02 (13)	C1—C2—H2	120.8
N1—C4—H4	118.0	C3—C2—H2	120.8
C5—C4—H4	118.0	C9—C10—C11	119.89 (13)
C3—N1—C4	116.93 (12)	C9—C10—H10	120.1
O1—C7—N2	120.69 (12)	C11—C10—H10	120.1
O1—C7—C8	120.42 (11)	C12—C11—C10	120.18 (14)
N2—C7—C8	118.89 (11)	C12—C11—H11	119.9
C10—C9—C8	121.57 (13)	C10—C11—H11	119.9
C10—C9—H9	119.2

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N1^i	0.86	2.16	2.986 (2)	160
O2—H2A···O1	0.82	1.80	2.529 (2)	147
C9—H9···N1^i	0.93	2.57	3.453 (2)	158

Symmetry code: (i) −x+5/2, y−1/2, z.