In the title compound, C
12H
9BrN
2O, the molecules assemble into
C(4) chains in the crystal structure by way of N—H
O bonds.
Supporting information
CCDC reference: 643055
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.037
- wR factor = 0.098
- Data-to-parameter ratio = 22.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.90
Alert level G
ABSTM02_ALERT_3_G 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 0.896
Tmax scaled 0.450 Tmin scaled 0.279
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
3 ALERT level G = General alerts; check
2 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
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
N-(2-Bromophenyl)pyridine-3-carboxamide
top
Crystal data top
C12H9BrN2O | F(000) = 1104 |
Mr = 277.12 | Dx = 1.633 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 5379 reflections |
a = 8.1505 (3) Å | θ = 2.8–27.3° |
b = 9.3471 (4) Å | µ = 3.63 mm−1 |
c = 29.5889 (13) Å | T = 293 K |
V = 2254.19 (16) Å3 | Chunk, colourless |
Z = 8 | 0.42 × 0.29 × 0.22 mm |
Data collection top
Bruker SMART1000 CCD area-detector diffractometer | 3296 independent reflections |
Radiation source: fine-focus sealed tube | 2009 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
ω scans | θmax = 30.0°, θmin = 2.8° |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | h = −11→11 |
Tmin = 0.311, Tmax = 0.503 | k = −13→11 |
21476 measured reflections | l = −41→41 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.098 | H-atom parameters constrained |
S = 0.94 | w = 1/[σ2(Fo2) + (0.0554P)2] where P = (Fo2 + 2Fc2)/3 |
3296 reflections | (Δ/σ)max < 0.001 |
145 parameters | Δρmax = 0.58 e Å−3 |
0 restraints | Δρmin = −0.59 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 | Uiso*/Ueq | |
C1 | 0.3580 (3) | 0.0622 (2) | 0.06625 (8) | 0.0402 (5) | |
C2 | 0.4874 (4) | 0.1246 (3) | 0.04307 (8) | 0.0584 (7) | |
H2 | 0.4664 | 0.1878 | 0.0195 | 0.070* | |
C3 | 0.6435 (3) | 0.0939 (3) | 0.05454 (10) | 0.0629 (8) | |
H3 | 0.7297 | 0.1369 | 0.0391 | 0.076* | |
C4 | 0.6761 (3) | −0.0008 (3) | 0.08914 (10) | 0.0608 (7) | |
H4 | 0.7840 | −0.0239 | 0.0963 | 0.073* | |
C5 | 0.5482 (3) | −0.0613 (2) | 0.11306 (8) | 0.0483 (5) | |
H5 | 0.5704 | −0.1249 | 0.1365 | 0.058* | |
C6 | 0.3867 (2) | −0.0280 (2) | 0.10241 (7) | 0.0353 (4) | |
C7 | 0.1563 (2) | −0.0060 (2) | 0.15370 (7) | 0.0338 (4) | |
C8 | 0.0300 (2) | −0.08479 (19) | 0.18032 (6) | 0.0317 (4) | |
C9 | −0.0347 (3) | −0.2155 (2) | 0.16750 (7) | 0.0426 (5) | |
H9 | 0.0002 | −0.2604 | 0.1411 | 0.051* | |
C10 | −0.1520 (3) | −0.2778 (2) | 0.19473 (9) | 0.0509 (6) | |
H10 | −0.1982 | −0.3652 | 0.1868 | 0.061* | |
C11 | −0.1994 (3) | −0.2096 (2) | 0.23337 (8) | 0.0494 (6) | |
H11 | −0.2780 | −0.2535 | 0.2514 | 0.059* | |
C12 | −0.0282 (3) | −0.0243 (2) | 0.21972 (8) | 0.0430 (5) | |
H12 | 0.0135 | 0.0645 | 0.2280 | 0.052* | |
N1 | 0.2579 (2) | −0.08809 (17) | 0.12826 (6) | 0.0372 (4) | |
H1 | 0.2436 | −0.1792 | 0.1278 | 0.045* | |
N2 | −0.1397 (2) | −0.0837 (2) | 0.24680 (7) | 0.0517 (5) | |
O1 | 0.16414 (19) | 0.12478 (15) | 0.15506 (6) | 0.0476 (4) | |
Br1 | 0.14114 (3) | 0.09641 (4) | 0.045835 (9) | 0.06657 (13) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0396 (11) | 0.0404 (11) | 0.0408 (11) | 0.0005 (9) | −0.0004 (9) | 0.0023 (9) |
C2 | 0.0658 (17) | 0.0604 (16) | 0.0490 (14) | −0.0060 (13) | 0.0119 (12) | 0.0144 (12) |
C3 | 0.0523 (16) | 0.0702 (19) | 0.0663 (17) | −0.0167 (14) | 0.0201 (13) | 0.0040 (14) |
C4 | 0.0372 (12) | 0.0708 (17) | 0.0746 (18) | 0.0031 (12) | 0.0039 (12) | −0.0033 (15) |
C5 | 0.0432 (13) | 0.0471 (12) | 0.0546 (13) | 0.0070 (10) | −0.0005 (11) | 0.0053 (11) |
C6 | 0.0371 (11) | 0.0277 (10) | 0.0410 (11) | −0.0001 (8) | 0.0038 (8) | −0.0012 (9) |
C7 | 0.0371 (10) | 0.0237 (10) | 0.0405 (10) | 0.0009 (8) | −0.0024 (8) | 0.0047 (8) |
C8 | 0.0325 (9) | 0.0245 (9) | 0.0381 (10) | 0.0030 (8) | −0.0023 (8) | 0.0061 (8) |
C9 | 0.0517 (12) | 0.0331 (11) | 0.0431 (11) | −0.0051 (10) | 0.0112 (10) | −0.0014 (9) |
C10 | 0.0569 (14) | 0.0357 (12) | 0.0601 (14) | −0.0120 (11) | 0.0140 (12) | −0.0023 (10) |
C11 | 0.0443 (12) | 0.0458 (14) | 0.0581 (14) | −0.0020 (10) | 0.0154 (11) | 0.0055 (11) |
C12 | 0.0387 (11) | 0.0366 (11) | 0.0535 (13) | 0.0027 (9) | 0.0026 (10) | −0.0036 (10) |
N1 | 0.0407 (9) | 0.0222 (8) | 0.0489 (9) | −0.0019 (7) | 0.0068 (8) | 0.0054 (7) |
N2 | 0.0499 (12) | 0.0504 (13) | 0.0548 (12) | 0.0016 (9) | 0.0131 (9) | −0.0053 (9) |
O1 | 0.0593 (10) | 0.0225 (7) | 0.0609 (10) | −0.0022 (7) | 0.0105 (8) | 0.0035 (6) |
Br1 | 0.05143 (17) | 0.0891 (3) | 0.05920 (18) | 0.00898 (14) | −0.00925 (12) | 0.02202 (14) |
Geometric parameters (Å, º) top
C1—C6 | 1.382 (3) | C7—N1 | 1.357 (3) |
C1—C2 | 1.386 (3) | C7—C8 | 1.491 (3) |
C1—Br1 | 1.895 (2) | C8—C12 | 1.380 (3) |
C2—C3 | 1.348 (4) | C8—C9 | 1.384 (3) |
C2—H2 | 0.9300 | C9—C10 | 1.379 (3) |
C3—C4 | 1.380 (4) | C9—H9 | 0.9300 |
C3—H3 | 0.9300 | C10—C11 | 1.365 (3) |
C4—C5 | 1.381 (3) | C10—H10 | 0.9300 |
C4—H4 | 0.9300 | C11—N2 | 1.333 (3) |
C5—C6 | 1.389 (3) | C11—H11 | 0.9300 |
C5—H5 | 0.9300 | C12—N2 | 1.333 (3) |
C6—N1 | 1.415 (3) | C12—H12 | 0.9300 |
C7—O1 | 1.225 (2) | N1—H1 | 0.8600 |
| | | |
C6—C1—C2 | 120.7 (2) | N1—C7—C8 | 115.81 (16) |
C6—C1—Br1 | 120.50 (16) | C12—C8—C9 | 117.56 (19) |
C2—C1—Br1 | 118.76 (18) | C12—C8—C7 | 118.77 (17) |
C3—C2—C1 | 120.3 (2) | C9—C8—C7 | 123.66 (18) |
C3—C2—H2 | 119.9 | C10—C9—C8 | 118.5 (2) |
C1—C2—H2 | 119.9 | C10—C9—H9 | 120.8 |
C2—C3—C4 | 120.4 (2) | C8—C9—H9 | 120.8 |
C2—C3—H3 | 119.8 | C11—C10—C9 | 119.2 (2) |
C4—C3—H3 | 119.8 | C11—C10—H10 | 120.4 |
C3—C4—C5 | 119.8 (2) | C9—C10—H10 | 120.4 |
C3—C4—H4 | 120.1 | N2—C11—C10 | 123.9 (2) |
C5—C4—H4 | 120.1 | N2—C11—H11 | 118.0 |
C4—C5—C6 | 120.5 (2) | C10—C11—H11 | 118.0 |
C4—C5—H5 | 119.8 | N2—C12—C8 | 124.9 (2) |
C6—C5—H5 | 119.8 | N2—C12—H12 | 117.6 |
C1—C6—C5 | 118.23 (19) | C8—C12—H12 | 117.6 |
C1—C6—N1 | 122.33 (18) | C7—N1—C6 | 121.88 (16) |
C5—C6—N1 | 119.43 (19) | C7—N1—H1 | 119.1 |
O1—C7—N1 | 123.43 (18) | C6—N1—H1 | 119.1 |
O1—C7—C8 | 120.75 (18) | C12—N2—C11 | 115.9 (2) |
| | | |
C6—C1—C2—C3 | 2.3 (4) | N1—C7—C8—C9 | −28.2 (3) |
Br1—C1—C2—C3 | −175.0 (2) | C12—C8—C9—C10 | −0.3 (3) |
C1—C2—C3—C4 | 0.7 (4) | C7—C8—C9—C10 | −179.5 (2) |
C2—C3—C4—C5 | −2.0 (4) | C8—C9—C10—C11 | −0.5 (4) |
C3—C4—C5—C6 | 0.3 (4) | C9—C10—C11—N2 | 0.5 (4) |
C2—C1—C6—C5 | −3.9 (3) | C9—C8—C12—N2 | 1.4 (3) |
Br1—C1—C6—C5 | 173.35 (17) | C7—C8—C12—N2 | −179.4 (2) |
C2—C1—C6—N1 | 176.9 (2) | O1—C7—N1—C6 | 2.7 (3) |
Br1—C1—C6—N1 | −5.9 (3) | C8—C7—N1—C6 | −178.00 (18) |
C4—C5—C6—C1 | 2.6 (3) | C1—C6—N1—C7 | −65.2 (3) |
C4—C5—C6—N1 | −178.2 (2) | C5—C6—N1—C7 | 115.6 (2) |
O1—C7—C8—C12 | −28.0 (3) | C8—C12—N2—C11 | −1.4 (3) |
N1—C7—C8—C12 | 152.63 (19) | C10—C11—N2—C12 | 0.5 (4) |
O1—C7—C8—C9 | 151.2 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 2.14 | 2.870 (2) | 143 |
Symmetry code: (i) −x+1/2, y−1/2, z. |