N-(2-Pyridylcarbon­yl)benzamide

The title compound, C₁₃H₁₀N₂O₂, has a Z,Z (trans–trans) arrangement of the central CONHCO group and an intra­molecular N—H...N hydrogen bond. The mol­ecule has a twisted conformation; the pyridine ring, which is almost parallel to the plane of the amide function at position 2, is inclined to the phenyl ring by 50.05 (6)°. In the crystal structure, symmetry-related mol­ecules are linked by C—H...O hydrogen bonds, forming a zigzag polymer chain extending in the a-axis direction. The chains are linked by a C—H...π inter­action involving phenyl rings of adjacent chains. There is also a π–π inter­action involving pyridine rings related by a center of symmetry.

Key indicators

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.032
• wR factor = 0.080
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT480_ALERT_4_A Long H...A H-Bond Reported H13    ..  B       ..       2.90 Ang.

Author Response: ...This involves a C---H...\p interaction, where B refers to the centroid of phenyl ring (C8---C13) related by the symmetry operation <i>x</i>, -<i>y</i> + 1/2,<i>z</i> - 1/2. See Comment section, last paragraph.

PLAT481_ALERT_4_A Long D...A H-Bond Reported C13    ..  B       ..       3.75 Ang.

Author Response: ...This involves a C---H...\p interaction, where B refers to the centroid of phenyl ring (C8---C13) related by the symmetry operation <i>x</i>, -<i>y</i> + 1/2,<i>z</i> - 1/2. See Comment section, last paragraph.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT716_ALERT_1_C H...A   Unknown or Inconsistent Label ..........          B
                    H13    B
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........          B
                    C13    B
PLAT718_ALERT_1_C D-H..A  Unknown or Inconsistent Label ..........          B
                    C13    H13    B

   2 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 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
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: EXPOSE (Stoe & Cie, 2000); cell refinement: CELL (Stoe & Cie, 2000); data reduction: INTEGRATE (Stoe & Cie, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

N-(2-Pyridylcarbonyl)benzamide

Crystal data

C13H10N2O2	F(000) = 472
Mr = 226.23	Dx = 1.392 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5665 reflections
a = 11.4673 (12) Å	θ = 2.3–25.9°
b = 13.8974 (11) Å	µ = 0.10 mm^−1
c = 6.9421 (8) Å	T = 153 K
β = 102.705 (13)°	Block, colourless
V = 1079.24 (19) Å^3	0.50 × 0.50 × 0.30 mm
Z = 4

Data collection

Stoe IPDS diffractometer	1483 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.062
Graphite monochromator	θmax = 25.9°, θmin = 2.3°
Detector resolution: 0.81Å pixels mm^-1	h = −13→13
φ oscillation scans	k = −16→17
8253 measured reflections	l = −8→8
2034 independent reflections

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	w = 1/[σ^2(Fo^2) + (0.0488P)^2] where P = (Fo^2 + 2Fc^2)/3
2034 reflections	(Δ/σ)max < 0.001
158 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

Experimental. ¹H-RMN (DMSO, 400 MHz): δ=11.49(s, 1H, H⁷), δ=8.75 (m, 1H, H⁵), δ=8.16 (m, 1H, H²), δ=8.10 (ddd, 1H, ³J(3,2)=³J(3,4)=7.65 Hz, ⁴J(3,5)=1.62 Hz, H³), δ=7.95 (dd, 2H, ³J(10,11)=7.88 Hz, ⁴J(10,12)=1.47 Hz, H¹⁰), δ=7.74 (m, 1H, H⁴), δ=7.68 (tt, 1H, ³J(12,11)=7.88 Hz, ⁴J(12,10)=1.47 Hz, H¹²), δ=7.58 (dd, 2H, ³J(11,10)=³J(11,12)= 7.88 Hz, H¹¹).

¹³C-RMN (DMSO, 400 MHz): δ=165.57 (1 C, C⁶), δ=163.17 (1 C, C⁸), δ=149.60 (1 C,C⁵), δ=149.19 (1 C, C¹), δ=139.44 (1 C, C³), δ=134.07 (1 C, C⁹), δ=133.99 (1 C,C¹²),δ=129.86 (1 C, C¹¹), δ=129.00 (1 C, C⁴), δ=128.63 (1 C, C¹⁰), δ=123.68 (1 C,C²).

ESI MS m/z: 249 ([M+Na]⁺)

IR (KBR disc, cm^-1): 3341(s), 2923(m), 2852(m), 1749(s), 1601(m), 1590(m), 1477(s), 1463(s), 1433(s), 1284(m), 1255(m), 1214(s), 1125(m), 1038(m), 998(m), 823(m), 789(m), 756(m), 727(m), 695(s), 613(s).

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.58732 (9)	0.28601 (6)	−0.01444 (14)	0.0331 (3)
O2	0.83619 (9)	0.31256 (6)	0.04587 (15)	0.0374 (3)
N1	0.56788 (10)	0.04517 (7)	−0.18379 (14)	0.0243 (3)
N2	0.73189 (10)	0.17122 (7)	−0.00952 (16)	0.0256 (3)
C1	0.52522 (11)	0.13157 (8)	−0.14481 (17)	0.0221 (4)
C2	0.40571 (12)	0.15526 (9)	−0.18869 (18)	0.0278 (4)
C3	0.32407 (13)	0.08651 (10)	−0.2809 (2)	0.0322 (5)
C4	0.36621 (12)	−0.00223 (9)	−0.32373 (18)	0.0296 (4)
C5	0.48742 (12)	−0.01979 (9)	−0.27195 (18)	0.0265 (4)
C6	0.61611 (12)	0.20507 (8)	−0.05141 (17)	0.0236 (4)
C7	0.83560 (12)	0.22511 (9)	0.04682 (17)	0.0249 (4)
C8	0.94742 (12)	0.16725 (8)	0.10538 (17)	0.0244 (4)
C9	0.94939 (13)	0.07861 (9)	0.19938 (19)	0.0287 (4)
C10	1.05619 (14)	0.02890 (10)	0.25807 (19)	0.0364 (5)
C11	1.16009 (15)	0.06681 (11)	0.2191 (2)	0.0416 (5)
C12	1.15848 (14)	0.15474 (12)	0.1243 (2)	0.0397 (5)
C13	1.05290 (13)	0.20580 (10)	0.06996 (19)	0.0324 (5)
H2	0.37970	0.21700	−0.15690	0.0330*
H2N	0.7400 (15)	0.1107 (13)	−0.042 (2)	0.045 (4)*
H3	0.24090	0.10030	−0.31370	0.0390*
H4	0.31260	−0.05040	−0.38780	0.0360*
H5	0.51540	−0.08140	−0.30040	0.0320*
H9	0.87750	0.05210	0.22340	0.0340*
H10	1.05790	−0.03100	0.32480	0.0440*
H11	1.23310	0.03240	0.25760	0.0500*
H12	1.23000	0.17990	0.09650	0.0480*
H13	1.05230	0.26700	0.00870	0.0390*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0317 (6)	0.0233 (5)	0.0432 (6)	0.0043 (4)	0.0062 (4)	−0.0041 (4)
O2	0.0324 (6)	0.0217 (5)	0.0549 (6)	−0.0033 (4)	0.0030 (5)	0.0016 (4)
N1	0.0248 (7)	0.0221 (5)	0.0260 (5)	0.0008 (4)	0.0053 (4)	0.0018 (4)
N2	0.0202 (7)	0.0189 (5)	0.0357 (6)	0.0009 (4)	0.0018 (4)	−0.0018 (4)
C1	0.0212 (8)	0.0229 (6)	0.0220 (6)	0.0016 (5)	0.0044 (5)	0.0035 (4)
C2	0.0234 (8)	0.0272 (6)	0.0324 (7)	0.0030 (5)	0.0050 (6)	0.0039 (5)
C3	0.0189 (8)	0.0388 (8)	0.0368 (8)	−0.0005 (6)	0.0014 (6)	0.0067 (6)
C4	0.0264 (9)	0.0324 (7)	0.0281 (7)	−0.0079 (6)	0.0017 (5)	0.0014 (5)
C5	0.0292 (9)	0.0232 (6)	0.0267 (6)	−0.0032 (5)	0.0056 (5)	0.0004 (5)
C6	0.0238 (8)	0.0225 (6)	0.0245 (6)	0.0033 (5)	0.0051 (5)	0.0024 (5)
C7	0.0248 (8)	0.0239 (6)	0.0247 (6)	−0.0020 (5)	0.0029 (5)	−0.0005 (5)
C8	0.0227 (8)	0.0268 (6)	0.0223 (6)	−0.0012 (5)	0.0017 (5)	−0.0042 (5)
C9	0.0283 (8)	0.0275 (7)	0.0297 (7)	0.0008 (5)	0.0052 (6)	−0.0018 (5)
C10	0.0404 (10)	0.0344 (7)	0.0310 (7)	0.0120 (7)	0.0004 (6)	−0.0016 (6)
C11	0.0285 (9)	0.0592 (10)	0.0321 (8)	0.0164 (7)	−0.0042 (6)	−0.0138 (7)
C12	0.0206 (9)	0.0622 (10)	0.0355 (8)	−0.0047 (7)	0.0042 (6)	−0.0112 (7)
C13	0.0253 (9)	0.0417 (8)	0.0288 (7)	−0.0060 (6)	0.0029 (6)	−0.0033 (6)

Geometric parameters (Å, º)

O1—C6	1.2155 (14)	C8—C9	1.3919 (17)
O2—C7	1.2154 (15)	C9—C10	1.387 (2)
N1—C1	1.3463 (15)	C10—C11	1.383 (2)
N1—C5	1.3388 (17)	C11—C12	1.386 (2)
N2—C6	1.3780 (18)	C12—C13	1.382 (2)
N2—C7	1.3870 (17)	C2—H2	0.9500
N2—H2N	0.881 (18)	C3—H3	0.9500
C1—C2	1.3769 (19)	C4—H4	0.9500
C1—C6	1.5010 (17)	C5—H5	0.9500
C2—C3	1.3912 (19)	C9—H9	0.9500
C3—C4	1.3806 (19)	C10—H10	0.9500
C4—C5	1.379 (2)	C11—H11	0.9500
C7—C8	1.4922 (19)	C12—H12	0.9500
C8—C13	1.393 (2)	C13—H13	0.9500
O1···O2	2.8161 (15)	C9···C11^vi	3.535 (2)
O1···C6^i	3.1607 (15)	C9···C10^vi	3.4974 (19)
O1···C4^ii	3.2358 (16)	C10···C9^vi	3.4974 (19)
O1···C5^ii	3.1078 (16)	C10···O2^x	3.4170 (17)
O1···C1^i	3.0344 (15)	C11···C3^xi	3.576 (2)
O2···O1	2.8161 (15)	C11···C9^vi	3.535 (2)
O2···C10^iii	3.4170 (17)	C4···H11^vii	3.0100
O2···C9^iv	3.3364 (17)	C8···H13^i	2.9400
O1···H5^ii	2.4000	C9···H13^i	3.0800
O1···H2	2.5600	C9···H2N	2.646 (16)
O1···H4^ii	2.7000	C11···H2N^vi	3.087 (17)
O2···H13	2.6200	C13···H13^i	3.0700
O2···H4^ii	2.6300	H2···O1	2.5600
O2···H10^iii	2.5600	H2···H12^xii	2.5800
N1···N2	2.6587 (15)	H2N···N1	2.200 (17)
N1···C5^v	3.3792 (16)	H2N···C9	2.646 (16)
N2···N1	2.6587 (15)	H2N···H9	2.2900
N1···H11^vi	2.6700	H2N···C11^vi	3.087 (17)
N1···H2N	2.200 (17)	H2N···H11^vi	2.5500
N2···H9	2.6400	H4···O1^viii	2.7000
C1···C5^v	3.3150 (17)	H4···O2^viii	2.6300
C1···O1^iv	3.0344 (15)	H5···O1^viii	2.4000
C3···C11^vii	3.576 (2)	H9···N2	2.6400
C4···O1^viii	3.2358 (16)	H9···H2N	2.2900
C4···C5^ix	3.5863 (19)	H10···O2^x	2.5600
C5···C5^ix	3.2883 (18)	H11···C4^xi	3.0100
C5···O1^viii	3.1078 (16)	H11···N1^vi	2.6700
C5···N1^v	3.3791 (16)	H11···H2N^vi	2.5500
C5···C1^v	3.3150 (17)	H12···H2^xiii	2.5800
C5···C4^ix	3.5863 (19)	H13···O2	2.6200
C6···O1^iv	3.1607 (15)	H13···C8^iv	2.9400
C7···C7^i	3.5393 (17)	H13···C9^iv	3.0800
C7···C7^iv	3.5393 (17)	H13···C13^iv	3.0700
C9···O2^i	3.3364 (17)
C1—N1—C5	116.68 (12)	C10—C11—C12	120.44 (15)
C6—N2—C7	127.00 (10)	C11—C12—C13	120.10 (15)
C7—N2—H2N	117.1 (11)	C8—C13—C12	119.78 (13)
C6—N2—H2N	115.0 (11)	C1—C2—H2	121.00
N1—C1—C6	116.44 (11)	C3—C2—H2	121.00
C2—C1—C6	119.71 (11)	C2—C3—H3	121.00
N1—C1—C2	123.83 (11)	C4—C3—H3	121.00
C1—C2—C3	118.29 (12)	C3—C4—H4	121.00
C2—C3—C4	118.72 (13)	C5—C4—H4	121.00
C3—C4—C5	118.85 (12)	N1—C5—H5	118.00
N1—C5—C4	123.62 (12)	C4—C5—H5	118.00
N2—C6—C1	113.84 (10)	C8—C9—H9	120.00
O1—C6—C1	121.73 (12)	C10—C9—H9	120.00
O1—C6—N2	124.42 (12)	C9—C10—H10	120.00
O2—C7—N2	122.95 (12)	C11—C10—H10	120.00
O2—C7—C8	122.33 (12)	C10—C11—H11	120.00
N2—C7—C8	114.71 (11)	C12—C11—H11	120.00
C7—C8—C9	121.94 (12)	C11—C12—H12	120.00
C9—C8—C13	119.86 (13)	C13—C12—H12	120.00
C7—C8—C13	118.17 (11)	C8—C13—H13	120.00
C8—C9—C10	120.05 (14)	C12—C13—H13	120.00
C9—C10—C11	119.73 (13)
C5—N1—C1—C2	0.59 (17)	C2—C3—C4—C5	0.60 (19)
C5—N1—C1—C6	−178.26 (10)	C3—C4—C5—N1	−0.87 (19)
C1—N1—C5—C4	0.28 (18)	O2—C7—C8—C9	147.55 (13)
C7—N2—C6—O1	−12.4 (2)	O2—C7—C8—C13	−30.17 (18)
C7—N2—C6—C1	168.96 (11)	N2—C7—C8—C9	−33.57 (16)
C6—N2—C7—O2	−8.1 (2)	N2—C7—C8—C13	148.71 (11)
C6—N2—C7—C8	173.07 (11)	C7—C8—C9—C10	−177.52 (12)
N1—C1—C2—C3	−0.82 (19)	C13—C8—C9—C10	0.16 (19)
C6—C1—C2—C3	177.99 (11)	C7—C8—C13—C12	179.26 (12)
N1—C1—C6—O1	178.24 (11)	C9—C8—C13—C12	1.49 (19)
N1—C1—C6—N2	−3.05 (15)	C8—C9—C10—C11	−1.35 (19)
C2—C1—C6—O1	−0.66 (18)	C9—C10—C11—C12	0.9 (2)
C2—C1—C6—N2	178.05 (11)	C10—C11—C12—C13	0.8 (2)
C1—C2—C3—C4	0.18 (19)	C11—C12—C13—C8	−2.0 (2)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+1, y+1/2, −z−1/2; (iii) −x+2, y+1/2, −z+1/2; (iv) x, −y+1/2, z−1/2; (v) −x+1, −y, −z; (vi) −x+2, −y, −z; (vii) x−1, y, z−1; (viii) −x+1, y−1/2, −z−1/2; (ix) −x+1, −y, −z−1; (x) −x+2, y−1/2, −z+1/2; (xi) x+1, y, z+1; (xii) x−1, −y+1/2, z−1/2; (xiii) x+1, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···N1	0.881 (18)	2.200 (17)	2.6587 (15)	112.0 (14)
C5—H5···O1^viii	0.95	2.40	3.1078 (16)	131
C10—H10···O2^x	0.95	2.56	3.4170 (17)	151
C13—H13···B^iv	0.95	2.90	3.7515 (18)	150

Symmetry codes: (iv) x, −y+1/2, z−1/2; (viii) −x+1, y−1/2, −z−1/2; (x) −x+2, y−1/2, −z+1/2.