N-(4-Bromo­phenyl)­pyridine-2-carbox­amide

In the title compound, C₁₂H₉BrN₂O, (I), the pyridyl and bromophenyl rings are almost coplanar. There is an intramolecular N—H...N hydrogen bond between the pyridine N atom and the amide N atom [N...N = 2.657 (3) Å and N—H...N = 112.6°].

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.041
• wR factor = 0.080
• Data-to-parameter ratio = 17.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



ABSTM_02  When printed, the submitted absorption T values will be replaced
          by the scaled T values. Since the ratio of scaled T's is
          identical to the ratio of reported T values, the scaling does
          not imply a change to the absorption corrections used in the
          study.
          Ratio of Tmax expected/reported      0.925
          Tmax scaled      0.515 Tmin scaled      0.414

---

Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SHELXTL-NT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT; software used to prepare material for publication: SHELXTL-NT.

N-(4-bromophenyl)pyridine-2-carboxamide

Crystal data

C12H9BrN2O	Z = 2
Mr = 277.12	F(000) = 276
Triclinic, P1	Dx = 1.662 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.2634 (11) Å	Cell parameters from 1232 reflections
b = 8.2355 (15) Å	θ = 1–27.5°
c = 10.9828 (18) Å	µ = 3.69 mm^−1
α = 88.282 (4)°	T = 294 K
β = 87.215 (4)°	Prism, yellow
γ = 78.268 (3)°	0.26 × 0.24 × 0.18 mm
V = 553.91 (17) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	2508 independent reflections
Radiation source: fine-focus sealed tube	1399 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
φ and ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.447, Tmax = 0.557	k = −10→9
3649 measured reflections	l = −11→14

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.080	w = 1/[σ^2(Fo^2) + (0.05P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
2508 reflections	Δρmax = 0.41 e Å^−3
145 parameters	Δρmin = −0.34 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
Br1	0.39058 (6)	0.24758 (4)	0.98994 (3)	0.07994 (12)
O1	−0.2752 (3)	0.7433 (2)	0.56771 (15)	0.0627 (5)
N1	0.0951 (3)	0.6821 (2)	0.55046 (17)	0.0477 (5)
H1A	0.2021	0.7001	0.5035	0.057*
N2	0.0937 (3)	0.8665 (2)	0.34769 (18)	0.0535 (6)
C1	−0.1050 (4)	0.7559 (3)	0.5144 (2)	0.0459 (7)
C2	−0.1015 (4)	0.8616 (3)	0.4007 (2)	0.0426 (6)
C3	−0.2958 (4)	0.9464 (3)	0.3559 (2)	0.0543 (7)
H3A	−0.4287	0.9379	0.3945	0.065*
C4	−0.2877 (5)	1.0436 (3)	0.2525 (2)	0.0628 (8)
H4A	−0.4154	1.1055	0.2216	0.075*
C5	−0.0896 (5)	1.0483 (3)	0.1956 (2)	0.0626 (8)
H5A	−0.0806	1.1105	0.1241	0.075*
C6	0.0950 (5)	0.9594 (3)	0.2462 (2)	0.0616 (8)
H6A	0.2291	0.9641	0.2075	0.074*
C7	0.1552 (4)	0.5799 (3)	0.6536 (2)	0.0425 (6)
C8	0.3740 (4)	0.5233 (3)	0.6701 (2)	0.0521 (7)
H8A	0.4760	0.5521	0.6136	0.063*
C9	0.4436 (4)	0.4248 (3)	0.7689 (2)	0.0570 (8)
H9A	0.5920	0.3863	0.7790	0.068*
C10	0.2924 (4)	0.3832 (3)	0.8532 (2)	0.0509 (7)
C11	0.0749 (4)	0.4384 (3)	0.8386 (2)	0.0528 (7)
H11A	−0.0260	0.4094	0.8958	0.063*
C12	0.0034 (4)	0.5378 (3)	0.7382 (2)	0.0496 (7)
H12A	−0.1451	0.5758	0.7280	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0902 (2)	0.0865 (2)	0.05585 (17)	−0.00160 (18)	−0.01512 (16)	0.02378 (15)
O1	0.0451 (11)	0.0725 (12)	0.0677 (11)	−0.0090 (9)	0.0002 (9)	0.0206 (10)
N1	0.0446 (12)	0.0515 (12)	0.0464 (11)	−0.0112 (10)	0.0009 (9)	0.0128 (10)
N2	0.0541 (14)	0.0492 (13)	0.0554 (13)	−0.0081 (11)	0.0001 (11)	0.0077 (10)
C1	0.0446 (15)	0.0445 (15)	0.0494 (15)	−0.0113 (12)	0.0013 (13)	−0.0024 (12)
C2	0.0467 (15)	0.0405 (14)	0.0412 (13)	−0.0101 (12)	−0.0026 (12)	0.0002 (11)
C3	0.0520 (17)	0.0584 (17)	0.0511 (15)	−0.0082 (14)	−0.0056 (13)	0.0056 (13)
C4	0.0669 (19)	0.0605 (18)	0.0586 (17)	−0.0049 (15)	−0.0180 (15)	0.0105 (14)
C5	0.085 (2)	0.0595 (18)	0.0447 (15)	−0.0186 (16)	−0.0096 (15)	0.0172 (13)
C6	0.0603 (18)	0.0658 (18)	0.0591 (17)	−0.0170 (15)	0.0027 (14)	0.0132 (15)
C7	0.0448 (15)	0.0429 (14)	0.0405 (13)	−0.0103 (12)	−0.0048 (11)	0.0031 (11)
C8	0.0458 (16)	0.0583 (17)	0.0521 (15)	−0.0127 (13)	0.0031 (12)	0.0087 (13)
C9	0.0467 (16)	0.0614 (17)	0.0605 (16)	−0.0056 (14)	−0.0064 (14)	0.0071 (14)
C10	0.0581 (17)	0.0519 (16)	0.0413 (14)	−0.0066 (14)	−0.0122 (13)	0.0046 (12)
C11	0.0580 (17)	0.0587 (16)	0.0427 (14)	−0.0164 (14)	0.0032 (13)	0.0073 (12)
C12	0.0413 (15)	0.0583 (17)	0.0482 (14)	−0.0087 (13)	−0.0027 (12)	0.0076 (13)

Geometric parameters (Å, º)

Br1—C10	1.895 (2)	C5—C6	1.370 (4)
O1—C1	1.213 (3)	C5—H5A	0.9300
N1—C1	1.349 (3)	C6—H6A	0.9300
N1—C7	1.410 (3)	C7—C8	1.374 (3)
N1—H1A	0.8600	C7—C12	1.384 (3)
N2—C6	1.334 (3)	C8—C9	1.369 (3)
N2—C2	1.336 (3)	C8—H8A	0.9300
C1—C2	1.502 (3)	C9—C10	1.379 (3)
C2—C3	1.380 (3)	C9—H9A	0.9300
C3—C4	1.374 (3)	C10—C11	1.361 (3)
C3—H3A	0.9300	C11—C12	1.389 (3)
C4—C5	1.369 (4)	C11—H11A	0.9300
C4—H4A	0.9300	C12—H12A	0.9300
C1—N1—C7	129.7 (2)	N2—C6—H6A	118.1
C1—N1—H1A	115.1	C5—C6—H6A	118.1
C7—N1—H1A	115.1	C8—C7—C12	119.6 (2)
C6—N2—C2	116.7 (2)	C8—C7—N1	117.7 (2)
O1—C1—N1	124.7 (2)	C12—C7—N1	122.6 (2)
O1—C1—C2	121.4 (2)	C9—C8—C7	120.8 (2)
N1—C1—C2	113.9 (2)	C9—C8—H8A	119.6
N2—C2—C3	123.5 (2)	C7—C8—H8A	119.6
N2—C2—C1	117.1 (2)	C8—C9—C10	119.6 (2)
C3—C2—C1	119.4 (2)	C8—C9—H9A	120.2
C4—C3—C2	118.2 (2)	C10—C9—H9A	120.2
C4—C3—H3A	120.9	C11—C10—C9	120.5 (2)
C2—C3—H3A	120.9	C11—C10—Br1	120.25 (19)
C5—C4—C3	119.3 (2)	C9—C10—Br1	119.2 (2)
C5—C4—H4A	120.4	C10—C11—C12	120.1 (2)
C3—C4—H4A	120.4	C10—C11—H11A	119.9
C4—C5—C6	118.6 (2)	C12—C11—H11A	119.9
C4—C5—H5A	120.7	C7—C12—C11	119.4 (2)
C6—C5—H5A	120.7	C7—C12—H12A	120.3
N2—C6—C5	123.8 (3)	C11—C12—H12A	120.3
C7—N1—C1—O1	−1.0 (4)	C4—C5—C6—N2	0.7 (4)
C7—N1—C1—C2	177.7 (2)	C1—N1—C7—C8	−178.6 (2)
C6—N2—C2—C3	0.0 (4)	C1—N1—C7—C12	0.3 (4)
C6—N2—C2—C1	179.4 (2)	C12—C7—C8—C9	0.4 (4)
O1—C1—C2—N2	−179.4 (2)	N1—C7—C8—C9	179.4 (2)
N1—C1—C2—N2	1.9 (3)	C7—C8—C9—C10	−0.5 (4)
O1—C1—C2—C3	0.0 (4)	C8—C9—C10—C11	0.4 (4)
N1—C1—C2—C3	−178.7 (2)	C8—C9—C10—Br1	−179.76 (19)
N2—C2—C3—C4	−1.4 (4)	C9—C10—C11—C12	−0.2 (4)
C1—C2—C3—C4	179.3 (2)	Br1—C10—C11—C12	180.00 (19)
C2—C3—C4—C5	2.4 (4)	C8—C7—C12—C11	−0.2 (4)
C3—C4—C5—C6	−2.0 (4)	N1—C7—C12—C11	−179.1 (2)
C2—N2—C6—C5	0.3 (4)	C10—C11—C12—C7	0.1 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2	0.86	2.20	2.657 (3)	113