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The title (1H-pyrrol-2-yl)­pyridines, C9H8N2, substituted at the ortho, meta, and para positions of the pyridine ring all have hydrogen-bonded arrangements with geometrically similar, nearly linear, N(pyrrole)—H...N(pyridine) hydrogen bonds of average length. The graph sets for the ortho, meta, and three para polymorphs are R_2^2(10), C(6), C(7), C(7), and R_4^4(28), respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103007042/kb1000sup1.cif
Contains datablocks global, I, II, IIIA, IIIB, IIIC

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103007042/kb1000Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103007042/kb1000IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103007042/kb1000IIIAsup4.hkl
Contains datablock IIIA

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103007042/kb1000IIIBsup5.hkl
Contains datablock IIIB

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103007042/kb1000IIICsup6.hkl
Contains datablock IIIC

CCDC references: 214174; 214175; 214176; 214177; 214178

Comment top

Pyrroles and other simple heteroaromatic nuclei are of interest in biology and medicine, and are used widely as ligands for transition metal complexes, including porphyrins and synthetic analogs (Klappa et al., 2002). Polypyrroles are of interest as conducting polymers (Wilson, 1997; de Jesus, 1996; Kanatzidis, 1990). We became interested in the (1H-pyrrol-2-yl)pyridines substituted in the ortho, (I), meta, (II), and para, (III), positions with respect to the N atom of the pyridine nucleus. We report here the crystal structures of (I), (II), and three polymorphs (III), viz. (IIIA), (IIIB) and (IIIC). In all three polymorphs, there are two molecules in the asymmetric unit.

The atomic labelling and the anisotropic displacement ellipsoids for the five structures are shown as part of the packing diagrams in Figs. 1–5. The bond lengths and angles are normal, and vary slightly in the pyridine rings, depending, in a reasonable way, on the point of attachment of the pyrrole ring. They agreed, within experimental error, in all eight determinations of the pyrrole-ring geometry.

The rings were all planar, with dihedral angles between the rings in (I) of 12.1 (2) and 5.0 (2)°, and between the rings in (IIIC) of 16.8 (5) and 8.3 (5)° for the two orientations of the disordered ring and 0.8 (2)° for the other. The disordered rings in (IIIC) are tilted in opposite directions to the plane of the pyrrole ring.

In all five structures, the molecules are held together by N8—H···N1 hydrogen bonds. The metrical parameters for these bonds are given in Table 1. A l l of the N—H···N bonds are close to linear and of average length.

In (I), there is an intramolecular N8—H···N1 contact, with N—H···N = 93°, H···N = 2.06 Å, and N···N = 2.786(?)Å. Although the N···N distance in this contact is shorter than the intermolecular N···N distances in all of the compounds, the geometry of the arrangement, with an N—H···N angle of 93°, suggests that it is less important. The intermolecular hydrogen-bond arrangement is shown in Fig. 1. Two molecules form a dimer across a twofold axis. In graph-set notation (Etter et al., 1990), this is an R22(10) arrangement.

The hydrogen bonding in (II) is shown in Fig. 2. There are chains, graph set C(6), lying along the [101] direction, with the molecules related by the n glide.

The hydrogen bonding in polymorph A of (III) is shown in Fig. 3. There are chains, graph set C(7), parallel to the b axis alternating between the crystallographically independent A and B molecules. The A and B molecules are not related by any pseudosymmetry. Pairs of molecules in the chain are related by translation along b. Although the molecules are crystallographically independent, there is no significant difference in their hydrogen-bonding behavior.

The hydrogen bonding in polymorph B of (III) is shown in Fig. 4. There are chains, graph set C(7), parallel to the c axis alternating between the crystallographically independent A and B molecules. As in polymorph A, there is no pseudosymmetry relating the two independent molecules and no significant difference in their hydrogen-bonding behavior. Adjacent pairs of A and B molecules in the chain are related by the c glide.

The bonding in polymorph C of (III) is shown in Fig. 5. There are four-membered rings, graph set R44(28), surrounding a center of symmetry, with alternating crystallographically independent A and B molecules. As a consequence of the molecular ring, the A and B molecules are related by a pseudo-fourfold symmetry axis, but this does not lead to more extended pseudosymmetry.

A comparison of the cell volumes of (IIIA), (IIIB), and (IIIC) [1495.6 (7), 1513.8 (7), and 1488.0 (7) Å3, respectively] suggests that the (IIIC) form is the most stable at low temperature and the (IIIB) form the least stable at low temperature (Dunitz, 1995).

Experimental top

The (1H-pyrrol-2-yl)pyridines (I)–(III) are well known compounds, and (I) is an inhibitor of prolyl 4-hydroxylase (Dowell et al., 1993). We chose methods that were (a) inexpensive, (b) relatively high-yielding, and (c) easily applied to acetophenones in order to generate a large variety of 2-aryl-1H-pyrroles for medicinal chemistry studies. A variation of the Knorr pyrrole synthesis (see Scheme below, method A) was suitable for easy formation of (II) and (III) (Kruse et al., 1987). The starting methyl ketones are, in general, inexpensive and readily available, and the intermediates require minimal purification. The synthesis of (I) was more difficult. Method A failed due to a very poor yield in the alkylation step and failure of the N,N-dimethylhydrazone to hydrolyze under several conditions. The problem was solved by preparing and utilizing 1-aryl-4-(N,N-dimethylhydrazono)-2-buten-1-ones (Severin et al., 1975) in two steps (see Scheme below, method B). The aldol step is rapid, but the cyclization step proceeded in lower yield, due in part, at least, to loss of product (I) because of its extremely high volatility. The literature melting points follow the usual pattern for aromatic compounds, with the para-isomer having the highest melting point, viz. 447–448 K (CCl4; Afonin et al., 2000); cf. the meta-isomer 373–375 K (benzene–petroleum ether; Pictet & Crepieux, 1895), and the ortho-isomer 361–362 K (petroleum ether;Petrova et al., 1997). The RF values (SiO2, 1:1 EtOAc, hexanes) among the isomers rose sharply from para (0.04) to meta (0.16) to ortho (0.49).

The initial attempt to grow crystals of (III) was made by recrystallization of a slightly impure sample (light brown in color) from methanol. The crystals were a mixture of dendrites and tear-shaped crystals. The sample was purified further; new crystals grown from acetonitrile appeared to be satisfactory for X-ray diffraction and the structure of (IIIA) was determined. It was then decided to check the unit cells on the original crystals. A needle, cut from a dendrite, had a different cell; the structure was determined as (IIIB). A tear-shaped crystal had a still different cell; the structure was determined as (IIIC). The melting point of (IIIA) was 445–447 K, in agreement with the literature value. The melting points of (IIIB) and (IIIC) were essentially the same, viz. 444–446 and 442–443 K, respectively, although both samples had shown some decomposition at about 430 K.

Refinement top

In all of the determinations, the H atoms were placed in idealized positions with respect to the attached atoms, except for those on the pyrrole N atoms; these were refined with isotropic displacement parameters. The ortho compound, (I), occurred in a non-centrosymmetric space group. However, with no atoms heavier than nitrogen in the structure, the absolute configuration could not be determined. The Friedel pairs were averaged for the final refinement. Disorder was found for the pyridine rings of molecule A in the (IIIC) polymorph; refinement using an ordered model with large anisotropic displacement parameters increased R from 0.057 to 0.061. The disorder parameter 0.475 (7) for the lesser component is not convincingly different from complete disorder. An intermolecular contact distance of 3.116 Å between atoms C2A' and C5A' in the next molecule along the a direction suggests the the two orientations probably alternate in adjacent molecules in this direction but are random between molecules in other directions.

Computing details top

For all compounds, data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The contacts in (I). Displacement ellipsoids are shown at the 50% probability level and H atoms are shown as small spheres of arbitrary radius. Intermolecular H···N contacts are shown as dashed lines.
[Figure 2] Fig. 2. The contacts in (II). Displacement ellipsoids are shown at the 50% probability level and H atoms are shown as small spheres of arbitrary radius. Intermolecular H···N contacts are shown as dashed lines.
[Figure 3] Fig. 3. The contacts in polymorph A of (III). Displacement ellipsoids are shown at the 50% probability level and H atoms are shown as small spheres of arbitrary radius. Intermolecular H···N contacts are shown as dashed lines.
[Figure 4] Fig. 4. The contacts in polymorph B of (III). Displacement ellipsoids are shown at the 50% probability level and H atoms are shown as small spheres of arbitrary radius. Intermolecular H···N contacts are shown as dashed lines.
[Figure 5] Fig. 5. The contacts in polymorph C of (III). Displacement ellipsoids are shown at the 50% probability level and H atoms are shown as small spheres of arbitrary radius. Intermolecular H···N contacts are shown as dashed lines. The disorder in the pyridine ring of molecule A is shown only in the labelled molecule.
(I) 2-(1H-pyrrol-2-yl)pyridine top
Crystal data top
C9H8N2Dx = 1.235 Mg m3
Mr = 144.17Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43212Cell parameters from 3961 reflections
Hall symbol: P 4nw 2abwθ = 2.6–26.4°
a = 8.123 (2) ŵ = 0.08 mm1
c = 23.502 (6) ÅT = 173 K
V = 1550.7 (7) Å3Prism, colorless
Z = 80.50 × 0.20 × 0.20 mm
F(000) = 608
Data collection top
Siemens SMART area-detector
diffractometer
1115 independent reflections
Radiation source: fine-focus sealed tube1052 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
ω scansθmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996; Blessing, 1995)
h = 1010
Tmin = 0.97, Tmax = 0.99k = 1010
18079 measured reflectionsl = 3030
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 1.16 w = 1/[σ2(Fo2) + (0.044P)2 + 0.304P]
where P = (Fo2 + 2Fc2)/3
1115 reflections(Δ/σ)max = 0.006
104 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = 0.16 e Å3
Crystal data top
C9H8N2Z = 8
Mr = 144.17Mo Kα radiation
Tetragonal, P43212µ = 0.08 mm1
a = 8.123 (2) ÅT = 173 K
c = 23.502 (6) Å0.50 × 0.20 × 0.20 mm
V = 1550.7 (7) Å3
Data collection top
Siemens SMART area-detector
diffractometer
1115 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996; Blessing, 1995)
1052 reflections with I > 2σ(I)
Tmin = 0.97, Tmax = 0.99Rint = 0.048
18079 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 1.16Δρmax = 0.13 e Å3
1115 reflectionsΔρmin = 0.16 e Å3
104 parameters
Special details top

Refinement. Since there are no atoms heavier than N, the Friedel pairs were averaged and no attempt was made to find the correct chirality.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.4647 (2)0.4615 (2)0.18006 (6)0.0336 (4)
C20.3648 (2)0.3306 (2)0.17355 (7)0.0311 (4)
C30.2546 (3)0.3197 (3)0.12807 (8)0.0401 (5)
H30.18370.22730.12450.048*
C40.2502 (3)0.4441 (3)0.08864 (8)0.0468 (5)
H40.17810.43700.05690.056*
C50.3505 (3)0.5793 (3)0.09517 (8)0.0436 (5)
H50.34840.66710.06850.052*
C60.4545 (3)0.5837 (3)0.14170 (8)0.0387 (5)
H60.52220.67790.14680.046*
C70.3808 (2)0.1975 (2)0.21452 (7)0.0322 (4)
N80.4717 (2)0.2180 (2)0.26351 (6)0.0339 (4)
H80.512 (3)0.316 (3)0.2768 (8)0.041 (6)*
C90.4817 (3)0.0717 (2)0.29148 (8)0.0393 (5)
H90.53770.05360.32640.047*
C100.3981 (3)0.0451 (3)0.26108 (8)0.0406 (5)
H100.38560.15790.27080.049*
C110.3340 (3)0.0339 (3)0.21249 (8)0.0397 (5)
H110.27000.01630.18350.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0348 (8)0.0359 (9)0.0302 (7)0.0003 (7)0.0003 (7)0.0018 (6)
C20.0295 (9)0.0351 (10)0.0287 (8)0.0025 (7)0.0013 (7)0.0065 (8)
C30.0387 (11)0.0418 (11)0.0397 (9)0.0025 (9)0.0069 (9)0.0039 (9)
C40.0449 (13)0.0558 (14)0.0398 (10)0.0000 (11)0.0128 (9)0.0032 (10)
C50.0431 (12)0.0488 (12)0.0389 (10)0.0021 (10)0.0050 (9)0.0105 (10)
C60.0382 (11)0.0383 (10)0.0396 (9)0.0031 (9)0.0004 (9)0.0015 (8)
C70.0307 (9)0.0359 (10)0.0300 (8)0.0010 (8)0.0003 (7)0.0042 (8)
N80.0377 (9)0.0349 (9)0.0291 (7)0.0030 (7)0.0017 (7)0.0011 (6)
C90.0416 (11)0.0415 (11)0.0348 (9)0.0017 (9)0.0005 (9)0.0040 (8)
C100.0463 (12)0.0328 (10)0.0427 (10)0.0030 (9)0.0010 (9)0.0049 (9)
C110.0428 (11)0.0382 (11)0.0381 (9)0.0040 (9)0.0021 (9)0.0037 (9)
Geometric parameters (Å, º) top
N1—C61.343 (2)C6—H60.9500
N1—C21.347 (2)C7—N81.378 (2)
C2—C31.397 (2)C7—C111.383 (3)
C2—C71.453 (3)N8—C91.361 (2)
C3—C41.372 (3)N8—H80.91 (2)
C3—H30.9500C9—C101.369 (3)
C4—C51.376 (3)C9—H90.9500
C4—H40.9500C10—C111.410 (3)
C5—C61.382 (3)C10—H100.9500
C5—H50.9500C11—H110.9500
C6—N1—C2118.07 (16)N8—C7—C11107.00 (17)
N1—C2—C3121.51 (18)N8—C7—C2120.79 (17)
N1—C2—C7117.26 (16)C11—C7—C2131.83 (17)
C3—C2—C7121.18 (17)C9—N8—C7109.28 (17)
C4—C3—C2119.17 (19)C9—N8—H8124.9 (12)
C4—C3—H3120.4C7—N8—H8125.6 (13)
C2—C3—H3120.4N8—C9—C10108.90 (17)
C3—C4—C5119.80 (19)N8—C9—H9125.6
C3—C4—H4120.1C10—C9—H9125.6
C5—C4—H4120.1C9—C10—C11106.86 (18)
C4—C5—C6118.1 (2)C9—C10—H10126.6
C4—C5—H5121.0C11—C10—H10126.6
C6—C5—H5121.0C7—C11—C10107.96 (18)
N1—C6—C5123.33 (19)C7—C11—H11126.0
N1—C6—H6118.3C10—C11—H11126.0
C5—C6—H6118.3
C6—N1—C2—C30.7 (3)N1—C2—C7—C11160.2 (2)
C6—N1—C2—C7178.28 (16)C3—C2—C7—C1117.4 (3)
N1—C2—C3—C41.1 (3)C11—C7—N8—C90.0 (2)
C7—C2—C3—C4176.36 (19)C2—C7—N8—C9173.71 (17)
C2—C3—C4—C51.7 (3)C7—N8—C9—C100.1 (2)
C3—C4—C5—C60.6 (3)N8—C9—C10—C110.2 (2)
C2—N1—C6—C52.0 (3)N8—C7—C11—C100.1 (2)
C4—C5—C6—N11.4 (3)C2—C7—C11—C10172.6 (2)
N1—C2—C7—N811.7 (3)C9—C10—C11—C70.1 (2)
C3—C2—C7—N8170.74 (17)
(II) 3-(1H-pyrrol-2-yl)pyridine top
Crystal data top
C9H8N2F(000) = 304
Mr = 144.17Dx = 1.293 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2058 reflections
a = 5.3537 (13) Åθ = 2.4–27.0°
b = 11.654 (3) ŵ = 0.08 mm1
c = 11.990 (3) ÅT = 174 K
β = 98.10 (1)°Needle, colorless
V = 740.6 (3) Å30.35 × 0.15 × 0.05 mm
Z = 4
Data collection top
Siemens SMART area-detector
diffractometer
1681 independent reflections
Radiation source: fine-focus sealed tube1232 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ω scansθmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996; Blessing, 1995)
h = 66
Tmin = 0.97, Tmax = 0.99k = 1115
4676 measured reflectionsl = 1514
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.058P)2 + 0.116P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
1681 reflectionsΔρmax = 0.19 e Å3
105 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.022 (6)
Crystal data top
C9H8N2V = 740.6 (3) Å3
Mr = 144.17Z = 4
Monoclinic, P21/nMo Kα radiation
a = 5.3537 (13) ŵ = 0.08 mm1
b = 11.654 (3) ÅT = 174 K
c = 11.990 (3) Å0.35 × 0.15 × 0.05 mm
β = 98.10 (1)°
Data collection top
Siemens SMART area-detector
diffractometer
1681 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996; Blessing, 1995)
1232 reflections with I > 2σ(I)
Tmin = 0.97, Tmax = 0.99Rint = 0.030
4676 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.19 e Å3
1681 reflectionsΔρmin = 0.17 e Å3
105 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.1570 (2)0.18720 (11)0.49705 (10)0.0382 (4)
C20.3451 (3)0.26068 (13)0.53070 (12)0.0353 (4)
H20.44230.28760.47560.042*
C30.4083 (2)0.30048 (12)0.64082 (11)0.0288 (3)
C40.2632 (3)0.25840 (13)0.72014 (12)0.0315 (4)
H40.29800.28220.79650.038*
C50.0695 (3)0.18224 (13)0.68719 (12)0.0343 (4)
H50.02980.15300.74050.041*
C60.0218 (3)0.14906 (13)0.57566 (12)0.0361 (4)
H60.11260.09700.55360.043*
C70.6152 (3)0.38164 (12)0.66867 (11)0.0296 (3)
N80.7188 (2)0.40504 (10)0.77786 (10)0.0309 (3)
H80.678 (3)0.3731 (15)0.8438 (14)0.044 (5)*
C90.9103 (3)0.48217 (13)0.77801 (13)0.0352 (4)
H91.01270.51150.84290.042*
C100.9299 (3)0.51011 (14)0.66894 (13)0.0381 (4)
H101.04630.56270.64430.046*
C110.7455 (3)0.44653 (13)0.59991 (13)0.0354 (4)
H110.71600.44800.51990.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0423 (7)0.0413 (8)0.0305 (7)0.0014 (6)0.0027 (5)0.0030 (6)
C20.0404 (8)0.0382 (8)0.0278 (8)0.0003 (7)0.0071 (6)0.0006 (6)
C30.0313 (7)0.0268 (7)0.0279 (7)0.0065 (6)0.0030 (5)0.0023 (6)
C40.0349 (7)0.0333 (8)0.0262 (7)0.0041 (6)0.0041 (6)0.0017 (6)
C50.0346 (8)0.0368 (8)0.0321 (8)0.0001 (7)0.0075 (6)0.0016 (6)
C60.0348 (7)0.0355 (8)0.0373 (8)0.0011 (7)0.0026 (6)0.0027 (7)
C70.0326 (7)0.0300 (7)0.0263 (7)0.0058 (6)0.0047 (6)0.0005 (6)
N80.0348 (6)0.0325 (7)0.0257 (7)0.0014 (5)0.0057 (5)0.0004 (5)
C90.0326 (8)0.0349 (8)0.0384 (9)0.0001 (7)0.0056 (6)0.0055 (6)
C100.0372 (8)0.0359 (8)0.0429 (9)0.0017 (7)0.0120 (7)0.0002 (7)
C110.0394 (8)0.0370 (8)0.0306 (8)0.0023 (7)0.0077 (6)0.0013 (6)
Geometric parameters (Å, º) top
N1—C21.340 (2)C6—H60.9500
N1—C61.342 (2)C7—N81.375 (2)
C2—C31.395 (2)C7—C111.379 (2)
C2—H20.9500N8—C91.364 (2)
C3—C41.399 (2)N8—H80.93 (2)
C3—C71.459 (2)C9—C101.366 (2)
C4—C51.380 (2)C9—H90.9500
C4—H40.9500C10—C111.406 (2)
C5—C61.381 (2)C10—H100.9500
C5—H50.9500C11—H110.9500
C2—N1—C6117.18 (13)N8—C7—C11106.86 (13)
N1—C2—C3124.70 (14)N8—C7—C3122.54 (12)
N1—C2—H2117.6C11—C7—C3130.60 (13)
C3—C2—H2117.6C9—N8—C7109.54 (12)
C2—C3—C4116.28 (13)C9—N8—H8122.1 (10)
C2—C3—C7120.49 (13)C7—N8—H8128.3 (10)
C4—C3—C7123.23 (13)N8—C9—C10108.36 (13)
C5—C4—C3119.87 (13)N8—C9—H9125.8
C5—C4—H4120.1C10—C9—H9125.8
C3—C4—H4120.1C9—C10—C11107.20 (14)
C4—C5—C6119.09 (14)C9—C10—H10126.4
C4—C5—H5120.5C11—C10—H10126.4
C6—C5—H5120.5C7—C11—C10108.04 (13)
N1—C6—C5122.88 (14)C7—C11—H11126.0
N1—C6—H6118.6C10—C11—H11126.0
C5—C6—H6118.6
C6—N1—C2—C30.4 (2)C2—C3—C7—C1113.0 (2)
N1—C2—C3—C40.6 (2)C4—C3—C7—C11166.92 (15)
N1—C2—C3—C7179.29 (13)C11—C7—N8—C90.31 (16)
C2—C3—C4—C50.3 (2)C3—C7—N8—C9178.97 (12)
C7—C3—C4—C5179.61 (13)C7—N8—C9—C100.67 (17)
C3—C4—C5—C60.2 (2)N8—C9—C10—C110.75 (17)
C2—N1—C6—C50.1 (2)N8—C7—C11—C100.15 (16)
C4—C5—C6—N10.4 (2)C3—C7—C11—C10179.36 (14)
C2—C3—C7—N8166.14 (13)C9—C10—C11—C70.56 (17)
C4—C3—C7—N814.0 (2)
(IIIA) 4-(1H-pyrrol-2-yl)pyridine top
Crystal data top
C9H8N2F(000) = 608
Mr = 144.17Dx = 1.281 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2036 reflections
a = 7.402 (2) Åθ = 2.9–25.4°
b = 11.480 (3) ŵ = 0.08 mm1
c = 17.705 (4) ÅT = 173 K
β = 96.23 (1)°Needle, colorless
V = 1495.6 (7) Å30.50 × 0.10 × 0.06 mm
Z = 8
Data collection top
Siemens SMART area-detector
diffractometer
3412 independent reflections
Radiation source: fine-focus sealed tube1933 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
ω scansθmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996; Blessing, 1995)
h = 99
Tmin = 0.97, Tmax = 0.99k = 1414
9224 measured reflectionsl = 1422
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.118 w = 1/[σ2(Fo2) + (0.058P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.92(Δ/σ)max = 0.001
3412 reflectionsΔρmax = 0.22 e Å3
208 parametersΔρmin = 0.21 e Å3
0 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0061 (13)
Crystal data top
C9H8N2V = 1495.6 (7) Å3
Mr = 144.17Z = 8
Monoclinic, P21/nMo Kα radiation
a = 7.402 (2) ŵ = 0.08 mm1
b = 11.480 (3) ÅT = 173 K
c = 17.705 (4) Å0.50 × 0.10 × 0.06 mm
β = 96.23 (1)°
Data collection top
Siemens SMART area-detector
diffractometer
3412 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996; Blessing, 1995)
1933 reflections with I > 2σ(I)
Tmin = 0.97, Tmax = 0.99Rint = 0.052
9224 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.118H atoms treated by a mixture of independent and constrained refinement
S = 0.92Δρmax = 0.22 e Å3
3412 reflectionsΔρmin = 0.21 e Å3
208 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N1A0.51651 (19)1.03326 (13)0.36614 (8)0.0342 (4)
C2A0.4940 (2)0.91726 (16)0.36095 (10)0.0339 (4)
H2A0.41050.88810.32090.041*
C3A0.5842 (2)0.83744 (15)0.40998 (10)0.0310 (4)
H3A0.56280.75640.40290.037*
C4A0.7073 (2)0.87705 (14)0.47014 (9)0.0269 (4)
C5A0.7320 (2)0.99727 (15)0.47522 (10)0.0313 (4)
H5A0.81521.02920.51440.038*
C6A0.6363 (2)1.06976 (16)0.42358 (10)0.0349 (5)
H6A0.65631.15120.42890.042*
C7A0.8068 (2)0.79937 (15)0.52473 (10)0.0284 (4)
N8A0.82073 (19)0.68110 (13)0.51256 (9)0.0320 (4)
H8A0.766 (3)0.6376 (18)0.4691 (13)0.069 (7)*
C9A0.9270 (2)0.63296 (17)0.57209 (11)0.0383 (5)
H9A0.95880.55290.57720.046*
C10A0.9804 (2)0.71855 (18)0.62330 (11)0.0419 (5)
H10A1.05460.70900.67010.050*
C11A0.9051 (2)0.82348 (16)0.59361 (10)0.0364 (5)
H11A0.91930.89790.61690.044*
N1B0.66800 (19)0.52851 (13)0.39051 (9)0.0370 (4)
C2B0.5705 (2)0.43542 (15)0.40684 (10)0.0326 (4)
H2B0.54900.42410.45830.039*
C3B0.4990 (2)0.35478 (14)0.35406 (9)0.0273 (4)
H3B0.42790.29180.36920.033*
C4B0.5318 (2)0.36635 (14)0.27840 (9)0.0256 (4)
C5B0.6355 (2)0.46278 (15)0.26074 (10)0.0328 (4)
H5B0.66240.47490.21010.039*
C6B0.6980 (2)0.53971 (16)0.31713 (11)0.0379 (5)
H6B0.76660.60490.30350.045*
C7B0.4594 (2)0.28416 (15)0.21977 (9)0.0270 (4)
N8B0.38293 (19)0.17978 (13)0.23726 (9)0.0315 (4)
H8B0.402 (3)0.1393 (17)0.2827 (12)0.064 (7)*
C9B0.3209 (2)0.12374 (17)0.17161 (11)0.0381 (5)
H9B0.26440.04930.16800.046*
C10B0.3541 (2)0.19336 (17)0.11157 (11)0.0401 (5)
H10B0.32300.17670.05920.048*
C11B0.4425 (2)0.29391 (16)0.14198 (10)0.0345 (5)
H11B0.48340.35730.11380.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0338 (8)0.0355 (10)0.0341 (9)0.0028 (7)0.0068 (7)0.0054 (7)
C2A0.0327 (10)0.0365 (11)0.0323 (11)0.0014 (8)0.0020 (8)0.0013 (8)
C3A0.0330 (9)0.0274 (10)0.0325 (10)0.0021 (8)0.0029 (8)0.0000 (8)
C4A0.0270 (8)0.0255 (9)0.0291 (10)0.0013 (7)0.0073 (7)0.0009 (7)
C5A0.0337 (9)0.0273 (10)0.0325 (10)0.0017 (8)0.0019 (8)0.0015 (8)
C6A0.0359 (10)0.0286 (11)0.0411 (12)0.0009 (8)0.0076 (9)0.0008 (9)
C7A0.0271 (9)0.0265 (10)0.0318 (10)0.0024 (7)0.0043 (8)0.0016 (8)
N8A0.0342 (8)0.0254 (8)0.0366 (10)0.0007 (7)0.0053 (7)0.0025 (7)
C9A0.0376 (10)0.0336 (11)0.0445 (12)0.0052 (9)0.0085 (9)0.0107 (9)
C10A0.0355 (10)0.0480 (13)0.0404 (12)0.0012 (9)0.0050 (9)0.0142 (10)
C11A0.0356 (10)0.0341 (11)0.0387 (11)0.0057 (8)0.0002 (8)0.0003 (9)
N1B0.0357 (8)0.0275 (9)0.0466 (10)0.0004 (7)0.0002 (7)0.0040 (7)
C2B0.0350 (10)0.0306 (11)0.0319 (10)0.0050 (8)0.0027 (8)0.0014 (8)
C3B0.0285 (9)0.0228 (9)0.0308 (10)0.0012 (7)0.0047 (7)0.0016 (7)
C4B0.0234 (8)0.0230 (9)0.0300 (10)0.0062 (7)0.0010 (7)0.0013 (7)
C5B0.0332 (9)0.0300 (10)0.0356 (11)0.0002 (8)0.0054 (8)0.0040 (8)
C6B0.0352 (10)0.0267 (11)0.0518 (13)0.0054 (8)0.0054 (9)0.0041 (9)
C7B0.0261 (9)0.0271 (10)0.0281 (10)0.0029 (7)0.0048 (7)0.0015 (8)
N8B0.0371 (8)0.0295 (9)0.0276 (9)0.0038 (7)0.0027 (7)0.0024 (7)
C9B0.0383 (10)0.0383 (12)0.0369 (11)0.0032 (9)0.0001 (9)0.0117 (9)
C10B0.0381 (10)0.0508 (13)0.0299 (11)0.0086 (9)0.0033 (8)0.0068 (10)
C11B0.0354 (10)0.0384 (11)0.0299 (11)0.0065 (8)0.0047 (8)0.0031 (8)
Geometric parameters (Å, º) top
N1A—C6A1.342 (2)N1B—C2B1.339 (2)
N1A—C2A1.344 (2)N1B—C6B1.348 (2)
C2A—C3A1.383 (2)C2B—C3B1.379 (2)
C2A—H2A0.9500C2B—H2B0.9500
C3A—C4A1.400 (2)C3B—C4B1.393 (2)
C3A—H3A0.9500C3B—H3B0.9500
C4A—C5A1.394 (2)C4B—C5B1.402 (2)
C4A—C7A1.455 (2)C4B—C7B1.461 (2)
C5A—C6A1.375 (2)C5B—C6B1.375 (2)
C5A—H5A0.9500C5B—H5B0.9500
C6A—H6A0.9500C6B—H6B0.9500
C7A—C11A1.379 (2)C7B—C11B1.374 (2)
C7A—N8A1.380 (2)C7B—N8B1.375 (2)
N8A—C9A1.362 (2)N8B—C9B1.364 (2)
N8A—H8A0.97 (2)N8B—H8B0.93 (2)
C9A—C10A1.366 (3)C9B—C10B1.373 (3)
C9A—H9A0.9500C9B—H9B0.9500
C10A—C11A1.405 (2)C10B—C11B1.405 (2)
C10A—H10A0.9500C10B—H10B0.9500
C11A—H11A0.9500C11B—H11B0.9500
C6A—N1A—C2A115.35 (15)C2B—N1B—C6B115.68 (16)
N1A—C2A—C3A124.46 (17)N1B—C2B—C3B124.44 (17)
N1A—C2A—H2A117.8N1B—C2B—H2B117.8
C3A—C2A—H2A117.8C3B—C2B—H2B117.8
C2A—C3A—C4A119.47 (16)C2B—C3B—C4B119.56 (16)
C2A—C3A—H3A120.3C2B—C3B—H3B120.2
C4A—C3A—H3A120.3C4B—C3B—H3B120.2
C5A—C4A—C3A116.16 (16)C3B—C4B—C5B116.51 (16)
C5A—C4A—C7A120.68 (15)C3B—C4B—C7B122.20 (15)
C3A—C4A—C7A123.16 (15)C5B—C4B—C7B121.28 (16)
C6A—C5A—C4A120.11 (16)C6B—C5B—C4B119.64 (17)
C6A—C5A—H5A119.9C6B—C5B—H5B120.2
C4A—C5A—H5A119.9C4B—C5B—H5B120.2
N1A—C6A—C5A124.44 (17)N1B—C6B—C5B124.14 (17)
N1A—C6A—H6A117.8N1B—C6B—H6B117.9
C5A—C6A—H6A117.8C5B—C6B—H6B117.9
C11A—C7A—N8A107.11 (16)C11B—C7B—N8B107.58 (15)
C11A—C7A—C4A130.17 (16)C11B—C7B—C4B130.24 (16)
N8A—C7A—C4A122.70 (15)N8B—C7B—C4B122.08 (15)
C9A—N8A—C7A108.97 (16)C9B—N8B—C7B109.14 (16)
C9A—N8A—H8A124.2 (12)C9B—N8B—H8B120.6 (13)
C7A—N8A—H8A126.8 (12)C7B—N8B—H8B127.3 (13)
N8A—C9A—C10A108.84 (17)N8B—C9B—C10B108.26 (17)
N8A—C9A—H9A125.6N8B—C9B—H9B125.9
C10A—C9A—H9A125.6C10B—C9B—H9B125.9
C9A—C10A—C11A107.08 (17)C9B—C10B—C11B107.25 (17)
C9A—C10A—H10A126.5C9B—C10B—H10B126.4
C11A—C10A—H10A126.5C11B—C10B—H10B126.4
C7A—C11A—C10A107.99 (17)C7B—C11B—C10B107.76 (16)
C7A—C11A—H11A126.0C7B—C11B—H11B126.1
C10A—C11A—H11A126.0C10B—C11B—H11B126.1
C6A—N1A—C2A—C3A0.2 (2)C6B—N1B—C2B—C3B1.3 (2)
N1A—C2A—C3A—C4A0.5 (3)N1B—C2B—C3B—C4B1.8 (2)
C2A—C3A—C4A—C5A1.0 (2)C2B—C3B—C4B—C5B1.0 (2)
C2A—C3A—C4A—C7A179.47 (15)C2B—C3B—C4B—C7B179.76 (15)
C3A—C4A—C5A—C6A0.9 (2)C3B—C4B—C5B—C6B0.2 (2)
C7A—C4A—C5A—C6A179.57 (15)C7B—C4B—C5B—C6B178.56 (15)
C2A—N1A—C6A—C5A0.3 (2)C2B—N1B—C6B—C5B0.1 (3)
C4A—C5A—C6A—N1A0.3 (3)C4B—C5B—C6B—N1B0.8 (3)
C5A—C4A—C7A—C11A13.8 (3)C3B—C4B—C7B—C11B164.02 (16)
C3A—C4A—C7A—C11A166.72 (17)C5B—C4B—C7B—C11B14.7 (3)
C5A—C4A—C7A—N8A164.32 (16)C3B—C4B—C7B—N8B11.9 (2)
C3A—C4A—C7A—N8A15.1 (2)C5B—C4B—C7B—N8B169.35 (14)
C11A—C7A—N8A—C9A0.69 (19)C11B—C7B—N8B—C9B0.77 (19)
C4A—C7A—N8A—C9A177.82 (14)C4B—C7B—N8B—C9B177.53 (14)
C7A—N8A—C9A—C10A0.7 (2)C7B—N8B—C9B—C10B1.2 (2)
N8A—C9A—C10A—C11A0.5 (2)N8B—C9B—C10B—C11B1.2 (2)
N8A—C7A—C11A—C10A0.38 (19)N8B—C7B—C11B—C10B0.01 (19)
C4A—C7A—C11A—C10A177.98 (16)C4B—C7B—C11B—C10B176.42 (16)
C9A—C10A—C11A—C7A0.1 (2)C9B—C10B—C11B—C7B0.7 (2)
(IIIB) 4-(1H-pyrrol-2-yl)pyridine top
Crystal data top
C9H8N2F(000) = 608
Mr = 144.17Dx = 1.265 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2651 reflections
a = 15.139 (4) Åθ = 2.2–25.8°
b = 5.4945 (14) ŵ = 0.08 mm1
c = 18.736 (5) ÅT = 173 K
β = 103.76 (1)°Needle, pale yellow
V = 1513.8 (7) Å30.50 × 0.05 × 0.05 mm
Z = 8
Data collection top
Siemens SMART area-detector
diffractometer
3452 independent reflections
Radiation source: fine-focus sealed tube2385 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
ω scansθmax = 27.5°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996; Blessing, 1995)
h = 1919
Tmin = 0.98, Tmax = 1.00k = 77
14309 measured reflectionsl = 2424
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.039P)2 + 0.333P]
where P = (Fo2 + 2Fc2)/3
3452 reflections(Δ/σ)max = 0.004
207 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C9H8N2V = 1513.8 (7) Å3
Mr = 144.17Z = 8
Monoclinic, P21/cMo Kα radiation
a = 15.139 (4) ŵ = 0.08 mm1
b = 5.4945 (14) ÅT = 173 K
c = 18.736 (5) Å0.50 × 0.05 × 0.05 mm
β = 103.76 (1)°
Data collection top
Siemens SMART area-detector
diffractometer
3452 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996; Blessing, 1995)
2385 reflections with I > 2σ(I)
Tmin = 0.98, Tmax = 1.00Rint = 0.049
14309 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.21 e Å3
3452 reflectionsΔρmin = 0.17 e Å3
207 parameters
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N1A0.27576 (9)0.3961 (3)0.53606 (7)0.0384 (3)
C2A0.29091 (10)0.1884 (3)0.50396 (8)0.0345 (4)
H2A0.35160.12940.51370.041*
C3A0.22412 (10)0.0537 (3)0.45747 (8)0.0323 (4)
H3A0.23950.09190.43590.039*
C4A0.13355 (10)0.1330 (3)0.44233 (8)0.0313 (3)
C5A0.11799 (11)0.3500 (3)0.47555 (9)0.0396 (4)
H5A0.05810.41380.46710.047*
C6A0.18896 (11)0.4721 (3)0.52049 (9)0.0428 (4)
H6A0.17580.62020.54200.051*
C7A0.05897 (10)0.0024 (3)0.39618 (8)0.0333 (4)
N8A0.07100 (9)0.1964 (3)0.35351 (7)0.0346 (3)
H8A0.1266 (12)0.251 (3)0.3465 (9)0.049 (5)*
C9A0.01126 (11)0.2884 (3)0.31821 (9)0.0410 (4)
H9A0.02100.42260.28530.049*
C10A0.07738 (11)0.1543 (4)0.33842 (10)0.0492 (5)
H10A0.14120.17880.32240.059*
C11A0.03390 (11)0.0253 (4)0.38697 (10)0.0486 (5)
H11A0.06300.14570.40970.058*
N1B0.23424 (9)0.8359 (3)0.80902 (7)0.0379 (3)
C2B0.23462 (11)0.6726 (3)0.75637 (9)0.0394 (4)
H2B0.19430.53810.75240.047*
C3B0.28941 (10)0.6856 (3)0.70726 (8)0.0349 (4)
H3B0.28650.56230.67120.042*
C4B0.34898 (9)0.8809 (3)0.71097 (8)0.0285 (3)
C5B0.34858 (10)1.0534 (3)0.76572 (9)0.0347 (4)
H5B0.38751.19110.77070.042*
C6B0.29178 (10)1.0235 (3)0.81231 (9)0.0380 (4)
H6B0.29331.14320.84920.046*
C7B0.41214 (9)0.9031 (3)0.66349 (8)0.0289 (3)
N8B0.41667 (9)0.7352 (3)0.60987 (7)0.0335 (3)
H8B0.3747 (12)0.614 (4)0.5915 (10)0.057 (6)*
C9B0.48412 (11)0.8000 (3)0.57681 (9)0.0387 (4)
H9B0.50040.71530.53760.046*
C10B0.52452 (10)1.0078 (3)0.60954 (9)0.0385 (4)
H10B0.57391.09180.59760.046*
C11B0.47941 (10)1.0736 (3)0.66395 (8)0.0342 (4)
H11B0.49271.21090.69550.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0398 (8)0.0369 (8)0.0374 (7)0.0027 (6)0.0068 (6)0.0036 (6)
C2A0.0307 (8)0.0378 (9)0.0341 (8)0.0008 (7)0.0064 (6)0.0003 (7)
C3A0.0326 (8)0.0335 (9)0.0312 (8)0.0010 (7)0.0081 (6)0.0028 (7)
C4A0.0317 (8)0.0362 (9)0.0273 (7)0.0002 (7)0.0098 (6)0.0019 (7)
C5A0.0330 (8)0.0416 (10)0.0435 (9)0.0058 (7)0.0080 (7)0.0036 (8)
C6A0.0464 (10)0.0359 (10)0.0465 (10)0.0016 (8)0.0120 (8)0.0081 (8)
C7A0.0310 (8)0.0375 (9)0.0320 (8)0.0011 (7)0.0088 (6)0.0022 (7)
N8A0.0307 (7)0.0407 (8)0.0322 (7)0.0007 (6)0.0075 (6)0.0034 (6)
C9A0.0370 (9)0.0462 (10)0.0368 (9)0.0079 (8)0.0030 (7)0.0057 (8)
C10A0.0294 (8)0.0605 (12)0.0553 (11)0.0045 (8)0.0053 (8)0.0081 (10)
C11A0.0317 (9)0.0568 (12)0.0585 (11)0.0004 (8)0.0129 (8)0.0153 (10)
N1B0.0360 (7)0.0435 (8)0.0352 (7)0.0003 (6)0.0106 (6)0.0025 (7)
C2B0.0361 (8)0.0404 (10)0.0416 (9)0.0105 (7)0.0088 (7)0.0001 (8)
C3B0.0370 (8)0.0338 (9)0.0334 (8)0.0064 (7)0.0077 (7)0.0058 (7)
C4B0.0260 (7)0.0302 (8)0.0270 (7)0.0020 (6)0.0018 (6)0.0034 (6)
C5B0.0341 (8)0.0321 (9)0.0375 (9)0.0040 (7)0.0078 (7)0.0034 (7)
C6B0.0397 (9)0.0383 (10)0.0361 (9)0.0002 (7)0.0095 (7)0.0043 (7)
C7B0.0293 (7)0.0284 (8)0.0264 (7)0.0003 (6)0.0016 (6)0.0006 (6)
N8B0.0337 (7)0.0346 (8)0.0320 (7)0.0011 (6)0.0073 (6)0.0017 (6)
C9B0.0358 (8)0.0487 (11)0.0335 (8)0.0060 (8)0.0121 (7)0.0030 (8)
C10B0.0301 (8)0.0502 (11)0.0351 (9)0.0033 (7)0.0072 (7)0.0075 (8)
C11B0.0302 (8)0.0382 (9)0.0311 (8)0.0054 (7)0.0014 (6)0.0017 (7)
Geometric parameters (Å, º) top
N1A—C2A1.335 (2)N1B—C2B1.335 (2)
N1A—C6A1.343 (2)N1B—C6B1.341 (2)
C2A—C3A1.382 (2)C2B—C3B1.379 (2)
C2A—H2A0.9500C2B—H2B0.9500
C3A—C4A1.402 (2)C3B—C4B1.393 (2)
C3A—H3A0.9500C3B—H3B0.9500
C4A—C5A1.391 (2)C4B—C5B1.398 (2)
C4A—C7A1.453 (2)C4B—C7B1.458 (2)
C5A—C6A1.372 (2)C5B—C6B1.373 (2)
C5A—H5A0.9500C5B—H5B0.9500
C6A—H6A0.9500C6B—H6B0.9500
C7A—N8A1.370 (2)C7B—N8B1.377 (2)
C7A—C11A1.384 (2)C7B—C11B1.382 (2)
N8A—C9A1.361 (2)N8B—C9B1.362 (2)
N8A—H8A0.931 (18)N8B—H8B0.929 (19)
C9A—C10A1.367 (2)C9B—C10B1.369 (2)
C9A—H9A0.9500C9B—H9B0.9500
C10A—C11A1.397 (2)C10B—C11B1.403 (2)
C10A—H10A0.9500C10B—H10B0.9500
C11A—H11A0.9500C11B—H11B0.9500
C2A—N1A—C6A115.60 (14)C2B—N1B—C6B115.69 (14)
N1A—C2A—C3A124.30 (14)N1B—C2B—C3B124.57 (15)
N1A—C2A—H2A117.8N1B—C2B—H2B117.7
C3A—C2A—H2A117.8C3B—C2B—H2B117.7
C2A—C3A—C4A119.64 (15)C2B—C3B—C4B119.44 (15)
C2A—C3A—H3A120.2C2B—C3B—H3B120.3
C4A—C3A—H3A120.2C4B—C3B—H3B120.3
C5A—C4A—C3A115.95 (14)C3B—C4B—C5B116.31 (14)
C5A—C4A—C7A120.99 (14)C3B—C4B—C7B123.02 (14)
C3A—C4A—C7A123.05 (14)C5B—C4B—C7B120.61 (14)
C6A—C5A—C4A120.18 (15)C6B—C5B—C4B119.88 (15)
C6A—C5A—H5A119.9C6B—C5B—H5B120.1
C4A—C5A—H5A119.9C4B—C5B—H5B120.1
N1A—C6A—C5A124.33 (16)N1B—C6B—C5B124.11 (15)
N1A—C6A—H6A117.8N1B—C6B—H6B117.9
C5A—C6A—H6A117.8C5B—C6B—H6B117.9
N8A—C7A—C11A106.56 (14)N8B—C7B—C11B107.10 (13)
N8A—C7A—C4A123.58 (14)N8B—C7B—C4B122.87 (14)
C11A—C7A—C4A129.83 (15)C11B—C7B—C4B129.94 (14)
C9A—N8A—C7A109.84 (14)C9B—N8B—C7B109.24 (14)
C9A—N8A—H8A124.4 (11)C9B—N8B—H8B122.7 (12)
C7A—N8A—H8A125.6 (11)C7B—N8B—H8B127.1 (12)
N8A—C9A—C10A108.11 (15)N8B—C9B—C10B108.52 (15)
N8A—C9A—H9A125.9N8B—C9B—H9B125.7
C10A—C9A—H9A125.9C10B—C9B—H9B125.7
C9A—C10A—C11A107.37 (15)C9B—C10B—C11B107.30 (14)
C9A—C10A—H10A126.3C9B—C10B—H10B126.3
C11A—C10A—H10A126.3C11B—C10B—H10B126.3
C7A—C11A—C10A108.12 (15)C7B—C11B—C10B107.82 (14)
C7A—C11A—H11A125.9C7B—C11B—H11B126.1
C10A—C11A—H11A125.9C10B—C11B—H11B126.1
C6A—N1A—C2A—C3A0.1 (2)C6B—N1B—C2B—C3B0.4 (2)
N1A—C2A—C3A—C4A0.7 (2)N1B—C2B—C3B—C4B0.4 (3)
C2A—C3A—C4A—C5A1.0 (2)C2B—C3B—C4B—C5B0.0 (2)
C2A—C3A—C4A—C7A177.77 (15)C2B—C3B—C4B—C7B177.12 (14)
C3A—C4A—C5A—C6A0.5 (2)C3B—C4B—C5B—C6B0.4 (2)
C7A—C4A—C5A—C6A178.31 (15)C7B—C4B—C5B—C6B176.81 (14)
C2A—N1A—C6A—C5A0.7 (2)C2B—N1B—C6B—C5B0.1 (2)
C4A—C5A—C6A—N1A0.4 (3)C4B—C5B—C6B—N1B0.4 (2)
C5A—C4A—C7A—N8A169.99 (15)C3B—C4B—C7B—N8B1.5 (2)
C3A—C4A—C7A—N8A11.3 (2)C5B—C4B—C7B—N8B178.50 (14)
C5A—C4A—C7A—C11A12.1 (3)C3B—C4B—C7B—C11B174.60 (15)
C3A—C4A—C7A—C11A166.58 (17)C5B—C4B—C7B—C11B2.4 (2)
C11A—C7A—N8A—C9A0.17 (18)C11B—C7B—N8B—C9B0.78 (17)
C4A—C7A—N8A—C9A178.48 (15)C4B—C7B—N8B—C9B177.66 (13)
C7A—N8A—C9A—C10A0.38 (19)C7B—N8B—C9B—C10B0.92 (18)
N8A—C9A—C10A—C11A0.4 (2)N8B—C9B—C10B—C11B0.68 (18)
N8A—C7A—C11A—C10A0.1 (2)N8B—C7B—C11B—C10B0.35 (17)
C4A—C7A—C11A—C10A178.07 (17)C4B—C7B—C11B—C10B176.93 (14)
C9A—C10A—C11A—C7A0.3 (2)C9B—C10B—C11B—C7B0.20 (18)
(IIIC) 4-(1H-pyrrol-2-yl)pyridine top
Crystal data top
C9H8N2F(000) = 608
Mr = 144.17Dx = 1.287 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2761 reflections
a = 5.1519 (13) Åθ = 2.8–26.2°
b = 19.739 (5) ŵ = 0.08 mm1
c = 14.694 (4) ÅT = 173 K
β = 95.26 (1)°Irregular, pale yellow
V = 1488.0 (7) Å30.45 × 0.15 × 0.05 mm
Z = 8
Data collection top
Siemens SMART area-detector
diffractometer
2920 independent reflections
Radiation source: fine-focus sealed tube1985 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
ω scansθmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996; Blessing, 1995)
h = 66
Tmin = 0.98, Tmax = 1.00k = 2124
8607 measured reflectionsl = 1814
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.111 w = 1/[σ2(Fo2) + (0.034P)2 + 0.258P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.002
2920 reflectionsΔρmax = 0.15 e Å3
227 parametersΔρmin = 0.12 e Å3
12 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0059 (13)
Crystal data top
C9H8N2V = 1488.0 (7) Å3
Mr = 144.17Z = 8
Monoclinic, P21/cMo Kα radiation
a = 5.1519 (13) ŵ = 0.08 mm1
b = 19.739 (5) ÅT = 173 K
c = 14.694 (4) Å0.45 × 0.15 × 0.05 mm
β = 95.26 (1)°
Data collection top
Siemens SMART area-detector
diffractometer
2920 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996; Blessing, 1995)
1985 reflections with I > 2σ(I)
Tmin = 0.98, Tmax = 1.00Rint = 0.042
8607 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05812 restraints
wR(F2) = 0.111H atoms treated by a mixture of independent and constrained refinement
S = 1.09Δρmax = 0.15 e Å3
2920 reflectionsΔρmin = 0.12 e Å3
227 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N1A0.559 (4)0.3845 (15)0.3992 (5)0.046 (3)0.525 (7)
C2A0.4897 (15)0.4178 (4)0.4718 (5)0.0510 (15)0.525 (7)
H2A0.36390.45290.46180.061*0.525 (7)
C3A0.5876 (16)0.4051 (4)0.5606 (5)0.0489 (16)0.525 (7)
H3A0.53550.43240.60890.059*0.525 (7)
C4A0.763 (6)0.3520 (19)0.5797 (7)0.0395 (15)0.525 (7)
C5A0.832 (2)0.3153 (6)0.5038 (10)0.050 (3)0.525 (7)
H5A0.95200.27880.51190.060*0.525 (7)
C6A0.725 (3)0.3324 (9)0.4178 (8)0.056 (3)0.525 (7)
H6A0.77100.30570.36790.067*0.525 (7)
N1A'0.540 (5)0.3729 (16)0.3969 (6)0.046 (3)0.475 (7)
C2A'0.4238 (17)0.3930 (4)0.4694 (6)0.0510 (15)0.475 (7)
H2A'0.26370.41690.45880.061*0.475 (7)
C3A'0.5191 (18)0.3817 (5)0.5589 (6)0.0489 (16)0.475 (7)
H3A'0.42370.39700.60730.059*0.475 (7)
C4A'0.755 (7)0.348 (2)0.5784 (8)0.0395 (15)0.475 (7)
C5A'0.887 (2)0.3297 (7)0.5025 (11)0.050 (3)0.475 (7)
H5A'1.05130.30780.51100.060*0.475 (7)
C6A'0.776 (3)0.3435 (10)0.4159 (9)0.056 (3)0.475 (7)
H6A'0.87090.33150.36600.067*0.475 (7)
C7A0.8633 (4)0.33406 (9)0.67166 (13)0.0393 (5)
N8A0.7479 (3)0.35683 (9)0.74647 (11)0.0444 (4)
H8A0.612 (4)0.3867 (11)0.7484 (13)0.056 (6)*
C9A0.8816 (4)0.33289 (11)0.82370 (14)0.0512 (6)
H9A0.84120.34150.88440.061*
C10A1.0844 (4)0.29430 (11)0.79918 (14)0.0536 (6)
H10A1.20970.27140.83950.064*
C11A1.0730 (4)0.29477 (10)0.70346 (14)0.0484 (5)
H11A1.18910.27210.66710.058*
N1B0.3322 (3)0.45933 (8)0.76455 (11)0.0455 (4)
C2B0.1425 (4)0.48763 (10)0.70906 (14)0.0465 (5)
H2B0.13230.47600.64610.056*
C3B0.0396 (4)0.53260 (10)0.73675 (13)0.0440 (5)
H3B0.17030.55040.69340.053*
C4B0.0322 (3)0.55191 (9)0.82781 (12)0.0372 (5)
C5B0.1636 (4)0.52192 (10)0.88640 (13)0.0446 (5)
H5B0.17770.53220.94980.054*
C6B0.3359 (4)0.47750 (10)0.85222 (14)0.0465 (5)
H6B0.46730.45830.89400.056*
C7B0.2144 (4)0.60047 (9)0.86040 (12)0.0381 (5)
N8B0.4080 (3)0.63014 (8)0.80317 (11)0.0402 (4)
H8B0.447 (4)0.6232 (9)0.7393 (13)0.049 (6)*
C9B0.5502 (4)0.67238 (10)0.85214 (14)0.0465 (5)
H9B0.69570.69850.82840.056*
C10B0.4484 (4)0.67091 (11)0.94137 (15)0.0529 (6)
H10B0.50930.69580.99050.063*
C11B0.2371 (4)0.62571 (10)0.94692 (13)0.0477 (5)
H11B0.12890.61451.00070.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.054 (3)0.036 (8)0.0480 (11)0.003 (5)0.0045 (10)0.0035 (13)
C2A0.051 (3)0.048 (4)0.0532 (16)0.009 (3)0.003 (2)0.000 (3)
C3A0.047 (4)0.053 (5)0.0469 (14)0.010 (3)0.003 (2)0.003 (3)
C4A0.0388 (17)0.030 (3)0.0497 (12)0.005 (2)0.0030 (10)0.0004 (11)
C5A0.053 (4)0.042 (5)0.0563 (16)0.009 (4)0.006 (3)0.003 (3)
C6A0.065 (5)0.050 (5)0.0518 (15)0.010 (5)0.009 (2)0.006 (2)
N1A'0.054 (3)0.036 (8)0.0480 (11)0.003 (5)0.0045 (10)0.0035 (13)
C2A'0.051 (3)0.048 (4)0.0532 (16)0.009 (3)0.003 (2)0.000 (3)
C3A'0.047 (4)0.053 (5)0.0469 (14)0.010 (3)0.003 (2)0.003 (3)
C4A'0.0388 (17)0.030 (3)0.0497 (12)0.005 (2)0.0030 (10)0.0004 (11)
C5A'0.053 (4)0.042 (5)0.0563 (16)0.009 (4)0.006 (3)0.003 (3)
C6A'0.065 (5)0.050 (5)0.0518 (15)0.010 (5)0.009 (2)0.006 (2)
C7A0.0388 (11)0.0318 (11)0.0471 (12)0.0019 (9)0.0026 (9)0.0013 (9)
N8A0.0437 (10)0.0438 (11)0.0453 (10)0.0009 (9)0.0024 (8)0.0032 (8)
C9A0.0501 (13)0.0549 (14)0.0475 (13)0.0066 (11)0.0016 (10)0.0082 (10)
C10A0.0484 (13)0.0487 (13)0.0613 (15)0.0026 (11)0.0087 (11)0.0132 (11)
C11A0.0441 (12)0.0384 (12)0.0620 (14)0.0026 (10)0.0017 (10)0.0021 (10)
N1B0.0419 (10)0.0415 (10)0.0533 (11)0.0023 (8)0.0047 (8)0.0028 (8)
C2B0.0476 (12)0.0453 (13)0.0467 (12)0.0022 (11)0.0045 (10)0.0039 (10)
C3B0.0415 (12)0.0464 (12)0.0440 (12)0.0032 (10)0.0022 (9)0.0003 (9)
C4B0.0353 (11)0.0347 (11)0.0417 (11)0.0077 (9)0.0040 (9)0.0011 (8)
C5B0.0451 (12)0.0462 (13)0.0425 (12)0.0027 (10)0.0043 (9)0.0025 (9)
C6B0.0416 (12)0.0475 (13)0.0501 (13)0.0014 (10)0.0024 (10)0.0073 (10)
C7B0.0366 (11)0.0354 (11)0.0422 (11)0.0068 (9)0.0029 (9)0.0006 (9)
N8B0.0410 (10)0.0362 (10)0.0437 (10)0.0023 (8)0.0054 (8)0.0021 (8)
C9B0.0464 (12)0.0380 (12)0.0566 (14)0.0017 (10)0.0123 (10)0.0016 (10)
C10B0.0584 (14)0.0446 (13)0.0579 (14)0.0054 (11)0.0176 (11)0.0096 (11)
C11B0.0504 (13)0.0487 (13)0.0441 (12)0.0085 (11)0.0050 (10)0.0023 (10)
Geometric parameters (Å, º) top
N1A—C2A1.331 (6)C9A—C10A1.368 (3)
N1A—C6A1.349 (9)C9A—H9A0.9500
C2A—C3A1.378 (3)C10A—C11A1.402 (3)
C2A—H2A0.9500C10A—H10A0.9500
C3A—C4A1.394 (9)C11A—H11A0.9500
C3A—H3A0.9500N1B—C6B1.336 (2)
C4A—C5A1.403 (9)N1B—C2B1.336 (2)
C4A—C7A1.447 (9)C2B—C3B1.380 (3)
C5A—C6A1.374 (3)C2B—H2B0.9500
C5A—H5A0.9500C3B—C4B1.388 (2)
C6A—H6A0.9500C3B—H3B0.9500
N1A'—C2A'1.331 (5)C4B—C5B1.396 (3)
N1A'—C6A'1.349 (10)C4B—C7B1.453 (3)
C2A'—C3A'1.378 (3)C5B—C6B1.375 (3)
C2A'—H2A'0.9500C5B—H5B0.9500
C3A'—C4A'1.394 (9)C6B—H6B0.9500
C3A'—H3A'0.9500C7B—N8B1.375 (2)
C4A'—C5A'1.403 (9)C7B—C11B1.380 (3)
C5A'—C6A'1.374 (3)N8B—C9B1.358 (2)
C5A'—H5A'0.9500N8B—H8B0.952 (19)
C6A'—H6A'0.9500C9B—C10B1.367 (3)
C7A—N8A1.372 (2)C9B—H9B0.9500
C7A—C11A1.377 (3)C10B—C11B1.404 (3)
N8A—C9A1.357 (2)C10B—H10B0.9500
N8A—H8A0.92 (2)C11B—H11B0.9500
C2A—N1A—C6A115.2 (3)C10A—C9A—H9A125.8
N1A—C2A—C3A124.6 (3)C9A—C10A—C11A107.33 (18)
N1A—C2A—H2A117.7C9A—C10A—H10A126.3
C3A—C2A—H2A117.7C11A—C10A—H10A126.3
C2A—C3A—C4A120.1 (3)C7A—C11A—C10A107.66 (19)
C2A—C3A—H3A119.9C7A—C11A—H11A126.2
C4A—C3A—H3A119.9C10A—C11A—H11A126.2
C3A—C4A—C5A115.8 (2)C6B—N1B—C2B114.92 (17)
C3A—C4A—C7A122.8 (9)N1B—C2B—C3B124.61 (19)
C5A—C4A—C7A121.4 (11)N1B—C2B—H2B117.7
C6A—C5A—C4A119.6 (4)C3B—C2B—H2B117.7
C6A—C5A—H5A120.2C2B—C3B—C4B120.09 (18)
C4A—C5A—H5A120.2C2B—C3B—H3B120.0
N1A—C6A—C5A124.5 (5)C4B—C3B—H3B120.0
N1A—C6A—H6A117.7C3B—C4B—C5B115.61 (18)
C5A—C6A—H6A117.7C3B—C4B—C7B122.49 (17)
C2A'—N1A'—C6A'115.2 (3)C5B—C4B—C7B121.89 (17)
N1A'—C2A'—C3A'124.6 (3)C6B—C5B—C4B119.95 (18)
N1A'—C2A'—H2A'117.7C6B—C5B—H5B120.0
C3A'—C2A'—H2A'117.7C4B—C5B—H5B120.0
C2A'—C3A'—C4A'120.1 (3)N1B—C6B—C5B124.80 (19)
C2A'—C3A'—H3A'119.9N1B—C6B—H6B117.6
C4A'—C3A'—H3A'119.9C5B—C6B—H6B117.6
C3A'—C4A'—C5A'115.8 (2)N8B—C7B—C11B106.94 (17)
C6A'—C5A'—C4A'119.6 (5)N8B—C7B—C4B122.25 (16)
C6A'—C5A'—H5A'120.2C11B—C7B—C4B130.81 (18)
C4A'—C5A'—H5A'120.2C9B—N8B—C7B109.49 (16)
N1A'—C6A'—C5A'124.5 (5)C9B—N8B—H8B122.5 (12)
N1A'—C6A'—H6A'117.7C7B—N8B—H8B128.0 (12)
C5A'—C6A'—H6A'117.7N8B—C9B—C10B108.48 (19)
N8A—C7A—C11A107.27 (17)N8B—C9B—H9B125.8
N8A—C7A—C4A121.6 (5)C10B—C9B—H9B125.8
C11A—C7A—C4A131.1 (5)C9B—C10B—C11B107.24 (19)
C9A—N8A—C7A109.38 (18)C9B—C10B—H10B126.4
C9A—N8A—H8A121.8 (12)C11B—C10B—H10B126.4
C7A—N8A—H8A128.5 (12)C7B—C11B—C10B107.86 (18)
N8A—C9A—C10A108.36 (19)C7B—C11B—H11B126.1
N8A—C9A—H9A125.8C10B—C11B—H11B126.1
C6A—N1A—C2A—C3A4 (3)N8A—C7A—C11A—C10A0.3 (2)
N1A—C2A—C3A—C4A3 (3)C4A—C7A—C11A—C10A180 (2)
C2A—C3A—C4A—C5A1 (4)C9A—C10A—C11A—C7A0.3 (2)
C2A—C3A—C4A—C7A177 (2)C6B—N1B—C2B—C3B0.2 (3)
C3A—C4A—C5A—C6A1 (4)N1B—C2B—C3B—C4B0.6 (3)
C7A—C4A—C5A—C6A178 (3)C2B—C3B—C4B—C5B1.3 (3)
C2A—N1A—C6A—C5A4 (4)C2B—C3B—C4B—C7B178.26 (18)
C4A—C5A—C6A—N1A2 (4)C3B—C4B—C5B—C6B1.2 (3)
C6A'—N1A'—C2A'—C3A'4 (4)C7B—C4B—C5B—C6B178.35 (18)
N1A'—C2A'—C3A'—C4A'1 (3)C2B—N1B—C6B—C5B0.3 (3)
C2A'—C3A'—C4A'—C5A'2 (5)C4B—C5B—C6B—N1B0.4 (3)
C3A'—C4A'—C5A'—C6A'2 (5)C3B—C4B—C7B—N8B0.6 (3)
C2A'—N1A'—C6A'—C5A'5 (4)C5B—C4B—C7B—N8B179.88 (17)
C4A'—C5A'—C6A'—N1A'2 (4)C3B—C4B—C7B—C11B179.8 (2)
C3A—C4A—C7A—N8A16 (5)C5B—C4B—C7B—C11B0.3 (3)
C5A—C4A—C7A—N8A162 (2)C11B—C7B—N8B—C9B0.5 (2)
C3A—C4A—C7A—C11A164.1 (19)C4B—C7B—N8B—C9B179.16 (17)
C5A—C4A—C7A—C11A18 (5)C7B—N8B—C9B—C10B0.5 (2)
C11A—C7A—N8A—C9A0.3 (2)N8B—C9B—C10B—C11B0.3 (2)
C4A—C7A—N8A—C9A180 (2)N8B—C7B—C11B—C10B0.3 (2)
C7A—N8A—C9A—C10A0.1 (2)C4B—C7B—C11B—C10B179.33 (19)
N8A—C9A—C10A—C11A0.1 (2)C9B—C10B—C11B—C7B0.0 (2)

Experimental details

(I)(II)(IIIA)(IIIB)
Crystal data
Chemical formulaC9H8N2C9H8N2C9H8N2C9H8N2
Mr144.17144.17144.17144.17
Crystal system, space groupTetragonal, P43212Monoclinic, P21/nMonoclinic, P21/nMonoclinic, P21/c
Temperature (K)173174173173
a, b, c (Å)8.123 (2), 8.123 (2), 23.502 (6)5.3537 (13), 11.654 (3), 11.990 (3)7.402 (2), 11.480 (3), 17.705 (4)15.139 (4), 5.4945 (14), 18.736 (5)
α, β, γ (°)90, 90, 9090, 98.10 (1), 9090, 96.23 (1), 9090, 103.76 (1), 90
V3)1550.7 (7)740.6 (3)1495.6 (7)1513.8 (7)
Z8488
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.080.080.080.08
Crystal size (mm)0.50 × 0.20 × 0.200.35 × 0.15 × 0.050.50 × 0.10 × 0.060.50 × 0.05 × 0.05
Data collection
DiffractometerSiemens SMART area-detector
diffractometer
Siemens SMART area-detector
diffractometer
Siemens SMART area-detector
diffractometer
Siemens SMART area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996; Blessing, 1995)
Multi-scan
(SADABS; Sheldrick, 1996; Blessing, 1995)
Multi-scan
(SADABS; Sheldrick, 1996; Blessing, 1995)
Multi-scan
(SADABS; Sheldrick, 1996; Blessing, 1995)
Tmin, Tmax0.97, 0.990.97, 0.990.97, 0.990.98, 1.00
No. of measured, independent and
observed [I > 2σ(I)] reflections
18079, 1115, 1052 4676, 1681, 1232 9224, 3412, 1933 14309, 3452, 2385
Rint0.0480.0300.0520.049
(sin θ/λ)max1)0.6500.6500.6490.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.100, 1.16 0.044, 0.114, 1.02 0.047, 0.118, 0.92 0.047, 0.098, 1.03
No. of reflections1115168134123452
No. of parameters104105208207
No. of restraints0000
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.13, 0.160.19, 0.170.22, 0.210.21, 0.17


(IIIC)
Crystal data
Chemical formulaC9H8N2
Mr144.17
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)5.1519 (13), 19.739 (5), 14.694 (4)
α, β, γ (°)90, 95.26 (1), 90
V3)1488.0 (7)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.45 × 0.15 × 0.05
Data collection
DiffractometerSiemens SMART area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996; Blessing, 1995)
Tmin, Tmax0.98, 1.00
No. of measured, independent and
observed [I > 2σ(I)] reflections
8607, 2920, 1985
Rint0.042
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.111, 1.09
No. of reflections2920
No. of parameters227
No. of restraints12
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.15, 0.12

Computer programs: SMART (Siemens, 1995), SAINT (Siemens, 1995), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL.

Distances and angles (Å, °) in the N8—H···N1 contacts in compounds (I)–(IIIC) top
DAD—HD—H···AH···AD···A
(I)N8N1i0.911632.062.949
(II)N8N1ii0.931691.992.901
(IIIA)N8AN1B0.971711.952.913
(IIIA)N8BN1iii0.931612.032.920
(IIIB)N8AN1Biv0.961681.942.891
(IIIB)N8BN1A0.951671.992.920
(IIIC)N8AN1B0.911742.072.976
(IIIC)N8BN1Av0.951742.083.021
(IIIC)N8BN1A'v0.951692.022.956
The s.u. values are N8—H and H.·N1 0.02 Å, N8—H···N1 1° and N8···N1 0.002–0.003 Å.

Symmetry codes: (i) 1 − y, 1 − x, 1/2 − z; (ii) −1/2 + x, 1/2 − y, −1/2 + z; (iii) x, −1 + y, z; (iv) x, 1/2 − y, −1/2 + z; (v) −x, 1 − y, 1 − z.
 

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