Literature DB >> 23723835

4-(1H-Pyrrolo-[2,3-b]pyridin-2-yl)pyridine.

Ping-Hsin Huang1, Yuh-Sheng Wen, Jiun-Yi Shen.   

Abstract

The asymmetric unit of the title compound, C12H9N3, contains two independent mol-ecules in which the dihedral angle between the n class="Chemical">pyridine and aza-indole rings are 8.23 (6) and 9.89 (2)°. In the crystal, both types of mol-ecule are connected by pairs of N-H-N hydrogen bonds into inversion dimers.

Entities:  

Year:  2013        PMID： 23723835      PMCID： PMC3647869          DOI： 10.1107/S1600536813008672

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the production of luminescent organic compounds, see: Liu et al. (2000 ▶); Parcerisa et al. (2008 ▶). For related structures, see: Huang et al. (2012 ▶).

Experimental

Crystal data

C12H9N3 M = 195.22 Triclinic, a = 6.5529 (5) Å b = 10.0457 (8) Å c = 14.5282 (11) Å α = 83.372 (2)° β = 86.697 (2)° γ = 87.427 (2)° V = 947.69 (13) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 295 K 0.30 × 0.20 × 0.05 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.975, T max = 0.996 10193 measured reflections 3329 independent reflections 2573 reflections with I > 2σ(I) R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.058 wR(F 2) = 0.124 S = 1.14 3329 reflections 271 parameters H-atom parameters constrained Δρmax = 0.14 e Å−3 Δρmin = −0.17 e Å−3 Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶). Click here for additional data file. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813008672/nc2308sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008672/nc2308Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813008672/nc2308Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C12H9N3Z = 4
Mr = 195.22F(000) = 408
Triclinic, P1Dx = 1.368 Mg m−3Dm = 1.368 Mg m−3Dm measured by not measured
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.5529 (5) ÅCell parameters from 1585 reflections
b = 10.0457 (8) Åθ = 2.6–23.3°
c = 14.5282 (11) ŵ = 0.09 mm−1
α = 83.372 (2)°T = 295 K
β = 86.697 (2)°Plate, colorless
γ = 87.427 (2)°0.30 × 0.20 × 0.05 mm
V = 947.69 (13) Å3
Bruker SMART APEX CCD area-detector diffractometer3329 independent reflections
Radiation source: fine-focus sealed tube2573 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −7→7
Tmin = 0.975, Tmax = 0.996k = −11→11
10193 measured reflectionsl = −17→17
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.14w = 1/[σ2(Fo2) + (0.0442P)2 + 0.126P] where P = (Fo2 + 2Fc2)/3
3329 reflections(Δ/σ)max < 0.001
271 parametersΔρmax = 0.14 e Å−3
0 restraintsΔρmin = −0.17 e Å−3
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.
xyzUiso*/Ueq
N10.2449 (3)0.99700 (17)0.92427 (12)0.0443 (5)
H10.17871.05680.95320.053*
N2−0.0037 (3)0.82637 (19)0.94609 (13)0.0523 (5)
N30.7664 (4)1.3698 (2)0.86462 (16)0.0704 (6)
N40.7252 (3)0.97632 (17)0.57580 (12)0.0452 (5)
H4A0.66511.04370.54500.054*
N50.4869 (3)0.80868 (19)0.55706 (13)0.0524 (5)
N61.2240 (4)1.3404 (2)0.62691 (16)0.0710 (6)
C10.4379 (3)1.0098 (2)0.88094 (14)0.0423 (5)
C20.4911 (3)0.8951 (2)0.84219 (15)0.0493 (6)
H20.61310.87800.80890.059*
C30.3285 (3)0.8067 (2)0.86152 (15)0.0435 (5)
C40.2881 (4)0.6784 (2)0.84216 (16)0.0548 (6)
H40.38260.62900.80830.066*
C50.1035 (4)0.6273 (2)0.87473 (17)0.0576 (7)
H50.07130.54180.86300.069*
C6−0.0344 (4)0.7025 (2)0.92484 (17)0.0589 (7)
H6−0.15800.66440.94540.071*
C70.1773 (3)0.8734 (2)0.91330 (14)0.0416 (5)
C80.5755 (5)1.3615 (3)0.90108 (19)0.0712 (8)
H80.51401.43760.92320.085*
C90.4636 (4)1.2481 (2)0.90816 (18)0.0603 (7)
H90.33011.24930.93370.072*
C100.5497 (3)1.1326 (2)0.87731 (14)0.0445 (5)
C110.7495 (4)1.1396 (2)0.84044 (16)0.0561 (6)
H110.81621.06440.81930.067*
C120.8479 (4)1.2578 (3)0.83527 (18)0.0678 (7)
H120.98111.25970.80940.081*
C130.9063 (3)0.9796 (2)0.61960 (14)0.0424 (5)
C140.9524 (3)0.8542 (2)0.66219 (15)0.0485 (6)
H141.06560.82930.69690.058*
C150.7970 (3)0.7688 (2)0.64396 (14)0.0436 (5)
C160.7536 (4)0.6348 (2)0.66723 (16)0.0554 (6)
H160.83950.57710.70350.066*
C170.5792 (4)0.5904 (2)0.63473 (17)0.0573 (6)
H170.54540.50120.64860.069*
C180.4535 (4)0.6788 (2)0.58133 (17)0.0557 (6)
H180.33660.64500.56070.067*
C190.6574 (3)0.8490 (2)0.58945 (14)0.0415 (5)
C201.0412 (5)1.3402 (3)0.59264 (18)0.0692 (8)
H200.98181.42250.57010.083*
C210.9327 (4)1.2275 (2)0.58795 (16)0.0566 (6)
H210.80441.23500.56310.068*
C221.0152 (3)1.1027 (2)0.62031 (14)0.0444 (5)
C231.2075 (4)1.1013 (2)0.65608 (17)0.0559 (6)
H231.27121.02050.67870.067*
C241.3034 (4)1.2199 (3)0.65792 (18)0.0672 (7)
H241.43191.21590.68240.081*
U11U22U33U12U13U23
N10.0419 (10)0.0413 (11)0.0508 (11)−0.0013 (8)0.0011 (9)−0.0113 (8)
N20.0454 (11)0.0507 (12)0.0623 (13)−0.0102 (9)0.0003 (9)−0.0112 (9)
N30.0765 (16)0.0626 (16)0.0714 (15)−0.0247 (13)−0.0063 (12)0.0053 (12)
N40.0435 (11)0.0392 (11)0.0524 (11)−0.0022 (8)−0.0088 (9)−0.0003 (8)
N50.0511 (12)0.0480 (12)0.0583 (12)−0.0112 (9)−0.0108 (9)0.0003 (9)
N60.0781 (17)0.0669 (16)0.0707 (15)−0.0277 (13)0.0007 (13)−0.0125 (12)
C10.0354 (12)0.0475 (14)0.0435 (13)−0.0009 (10)−0.0020 (10)−0.0034 (10)
C20.0432 (13)0.0539 (15)0.0498 (14)0.0005 (11)0.0038 (11)−0.0054 (11)
C30.0457 (13)0.0409 (13)0.0441 (13)0.0020 (10)−0.0037 (10)−0.0057 (10)
C40.0627 (16)0.0474 (15)0.0542 (15)0.0029 (12)0.0004 (12)−0.0089 (11)
C50.0703 (17)0.0414 (14)0.0629 (16)−0.0094 (12)−0.0066 (13)−0.0096 (11)
C60.0570 (15)0.0540 (16)0.0674 (17)−0.0163 (12)−0.0014 (13)−0.0095 (13)
C70.0408 (12)0.0412 (13)0.0439 (13)−0.0038 (10)−0.0064 (10)−0.0062 (10)
C80.080 (2)0.0510 (17)0.083 (2)−0.0045 (14)−0.0019 (16)−0.0076 (14)
C90.0568 (15)0.0499 (16)0.0747 (18)−0.0087 (12)0.0038 (13)−0.0109 (13)
C100.0477 (13)0.0461 (14)0.0394 (12)−0.0052 (10)−0.0064 (10)0.0002 (10)
C110.0500 (14)0.0573 (16)0.0607 (16)−0.0104 (12)0.0045 (12)−0.0049 (12)
C120.0593 (17)0.076 (2)0.0665 (18)−0.0216 (15)0.0066 (13)0.0018 (15)
C130.0394 (12)0.0457 (14)0.0423 (12)−0.0011 (10)−0.0029 (10)−0.0059 (10)
C140.0448 (13)0.0499 (15)0.0509 (14)0.0019 (11)−0.0111 (11)−0.0034 (11)
C150.0465 (13)0.0395 (13)0.0439 (13)0.0006 (10)−0.0027 (10)−0.0016 (10)
C160.0632 (16)0.0461 (15)0.0559 (15)0.0016 (12)−0.0070 (12)−0.0009 (11)
C170.0707 (17)0.0407 (14)0.0604 (16)−0.0123 (12)−0.0045 (13)−0.0010 (11)
C180.0556 (15)0.0524 (16)0.0595 (15)−0.0157 (12)−0.0078 (12)−0.0004 (12)
C190.0431 (12)0.0385 (13)0.0429 (12)−0.0062 (10)−0.0006 (10)−0.0040 (9)
C200.087 (2)0.0538 (17)0.0668 (18)−0.0156 (15)−0.0081 (16)0.0007 (13)
C210.0595 (15)0.0505 (15)0.0601 (16)−0.0079 (12)−0.0115 (12)−0.0013 (12)
C220.0440 (13)0.0497 (14)0.0403 (13)−0.0053 (10)0.0007 (10)−0.0083 (10)
C230.0494 (14)0.0582 (16)0.0618 (16)−0.0072 (12)−0.0079 (12)−0.0093 (12)
C240.0570 (16)0.082 (2)0.0658 (18)−0.0206 (15)−0.0063 (13)−0.0156 (15)
N1—C71.366 (2)C8—H80.9300
N1—C11.384 (2)C9—C101.378 (3)
N1—H10.8600C9—H90.9300
N2—C71.338 (3)C10—C111.387 (3)
N2—C61.343 (3)C11—C121.368 (3)
N3—C121.329 (3)C11—H110.9300
N3—C81.332 (3)C12—H120.9300
N4—C191.362 (3)C13—C141.367 (3)
N4—C131.382 (2)C13—C221.457 (3)
N4—H4A0.8600C14—C151.416 (3)
N5—C191.334 (3)C14—H140.9300
N5—C181.336 (3)C15—C161.388 (3)
N6—C201.324 (3)C15—C191.408 (3)
N6—C241.336 (3)C16—C171.373 (3)
C1—C21.362 (3)C16—H160.9300
C1—C101.457 (3)C17—C181.384 (3)
C2—C31.413 (3)C17—H170.9300
C2—H20.9300C18—H180.9300
C3—C41.390 (3)C20—C211.374 (3)
C3—C71.403 (3)C20—H200.9300
C4—C51.373 (3)C21—C221.384 (3)
C4—H40.9300C21—H210.9300
C5—C61.381 (3)C22—C231.390 (3)
C5—H50.9300C23—C241.375 (3)
C6—H60.9300C23—H230.9300
C8—C91.373 (3)C24—H240.9300
C7—N1—C1108.49 (17)C12—C11—H11120.1
C7—N1—H1125.8C10—C11—H11120.1
C1—N1—H1125.8N3—C12—C11124.5 (3)
C7—N2—C6113.4 (2)N3—C12—H12117.7
C12—N3—C8115.3 (2)C11—C12—H12117.7
C19—N4—C13108.82 (17)C14—C13—N4108.76 (19)
C19—N4—H4A125.6C14—C13—C22128.8 (2)
C13—N4—H4A125.6N4—C13—C22122.39 (19)
C19—N5—C18113.62 (19)C13—C14—C15107.79 (19)
C20—N6—C24115.3 (2)C13—C14—H14126.1
C2—C1—N1108.75 (19)C15—C14—H14126.1
C2—C1—C10129.1 (2)C16—C15—C19117.3 (2)
N1—C1—C10122.06 (19)C16—C15—C14136.3 (2)
C1—C2—C3108.01 (19)C19—C15—C14106.40 (18)
C1—C2—H2126.0C17—C16—C15117.6 (2)
C3—C2—H2126.0C17—C16—H16121.2
C4—C3—C7117.2 (2)C15—C16—H16121.2
C4—C3—C2136.3 (2)C16—C17—C18119.9 (2)
C7—C3—C2106.46 (19)C16—C17—H17120.0
C5—C4—C3117.6 (2)C18—C17—H17120.0
C5—C4—H4121.2N5—C18—C17125.2 (2)
C3—C4—H4121.2N5—C18—H18117.4
C4—C5—C6120.1 (2)C17—C18—H18117.4
C4—C5—H5119.9N5—C19—N4125.41 (19)
C6—C5—H5119.9N5—C19—C15126.4 (2)
N2—C6—C5125.0 (2)N4—C19—C15108.23 (18)
N2—C6—H6117.5N6—C20—C21124.8 (3)
C5—C6—H6117.5N6—C20—H20117.6
N2—C7—N1125.10 (19)C21—C20—H20117.6
N2—C7—C3126.6 (2)C20—C21—C22119.7 (2)
N1—C7—C3108.29 (18)C20—C21—H21120.2
N3—C8—C9124.4 (3)C22—C21—H21120.2
N3—C8—H8117.8C21—C22—C23116.1 (2)
C9—C8—H8117.8C21—C22—C13122.5 (2)
C8—C9—C10119.7 (2)C23—C22—C13121.3 (2)
C8—C9—H9120.1C24—C23—C22119.7 (2)
C10—C9—H9120.1C24—C23—H23120.1
C9—C10—C11116.3 (2)C22—C23—H23120.1
C9—C10—C1122.5 (2)N6—C24—C23124.3 (2)
C11—C10—C1121.1 (2)N6—C24—H24117.8
C12—C11—C10119.7 (2)C23—C24—H24117.8
C7—N1—C1—C20.5 (2)C19—N4—C13—C14−0.7 (2)
C7—N1—C1—C10177.80 (18)C19—N4—C13—C22−178.17 (19)
N1—C1—C2—C3−0.2 (2)N4—C13—C14—C150.6 (2)
C10—C1—C2—C3−177.3 (2)C22—C13—C14—C15177.8 (2)
C1—C2—C3—C4179.9 (2)C13—C14—C15—C16−179.2 (3)
C1—C2—C3—C7−0.1 (2)C13—C14—C15—C19−0.3 (2)
C7—C3—C4—C50.3 (3)C19—C15—C16—C170.5 (3)
C2—C3—C4—C5−179.7 (2)C14—C15—C16—C17179.3 (2)
C3—C4—C5—C60.0 (4)C15—C16—C17—C18−0.4 (4)
C7—N2—C6—C50.4 (3)C19—N5—C18—C170.0 (3)
C4—C5—C6—N2−0.3 (4)C16—C17—C18—N50.1 (4)
C6—N2—C7—N1179.2 (2)C18—N5—C19—N4−179.1 (2)
C6—N2—C7—C3−0.1 (3)C18—N5—C19—C150.2 (3)
C1—N1—C7—N2−179.9 (2)C13—N4—C19—N5180.0 (2)
C1—N1—C7—C3−0.5 (2)C13—N4—C19—C150.6 (2)
C4—C3—C7—N2−0.2 (3)C16—C15—C19—N5−0.5 (3)
C2—C3—C7—N2179.8 (2)C14—C15—C19—N5−179.6 (2)
C4—C3—C7—N1−179.60 (18)C16—C15—C19—N4178.96 (19)
C2—C3—C7—N10.4 (2)C14—C15—C19—N4−0.2 (2)
C12—N3—C8—C9−0.9 (4)C24—N6—C20—C210.4 (4)
N3—C8—C9—C100.8 (4)N6—C20—C21—C22−0.3 (4)
C8—C9—C10—C110.2 (4)C20—C21—C22—C23−0.1 (3)
C8—C9—C10—C1−178.6 (2)C20—C21—C22—C13178.4 (2)
C2—C1—C10—C9170.0 (2)C14—C13—C22—C21−168.3 (2)
N1—C1—C10—C9−6.7 (3)N4—C13—C22—C218.6 (3)
C2—C1—C10—C11−8.7 (4)C14—C13—C22—C2310.1 (3)
N1—C1—C10—C11174.5 (2)N4—C13—C22—C23−173.0 (2)
C9—C10—C11—C12−0.9 (3)C21—C22—C23—C240.2 (3)
C1—C10—C11—C12177.9 (2)C13—C22—C23—C24−178.2 (2)
C8—N3—C12—C110.0 (4)C20—N6—C24—C23−0.2 (4)
C10—C11—C12—N30.9 (4)C22—C23—C24—N6−0.1 (4)
D—H···AD—HH···AD···AD—H···A
N1—H1···N2i0.862.223.061 (3)167
N4—H4A···N5ii0.862.223.066 (3)169
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
N1—H1⋯N2i 0.862.223.061 (3)167
N4—H4A⋯N5ii 0.862.223.066 (3)169

Symmetry codes: (i) ; (ii) .

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