The dipharmacophore compound 3-cyclopropyl-5-(3-methyl-[1,2,4]triazolo[4,3-
a]pyridin-7-yl)-1,2,4-oxadiazole, C
12H
11N
5O, was studied on the assumption of its potential biological activity. Two polymorphic forms differ in both their molecular and crystal structures. The monoclinic polymorphic form was crystallized from more volatile solvents and contains a conformer with a higher relative energy. The basic molecule forms an abundance of interactions with relatively close energies. The orthorhombic polymorph was crystallized very slowly from isoamyl alcohol and contains a conformer with a much lower energy. The basic molecule forms two strong interactions and a large number of weak interactions. Stacking interactions of the `head-to-head' type in the monoclinic structure and of the `head-to-tail' type in the orthorhombic structure proved to be the strongest and form stacked columns in the two polymorphs. The main structural motif of the monoclinic structure is a double column where two stacked columns interact through weak C—H
N hydrogen bonds and dispersive interactions. In the orthorhombic structure, a single stacked column is the main structural motif. Periodic calculations confirmed that the orthorhombic structure obtained by slow evaporation has a lower lattice energy (0.97 kcal mol
−1) compared to the monoclinic structure.
Supporting information
CCDC references: 2025658; 2025657
For both structures, data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015b).
3-Cyclopropyl-5-(3-methyl-[1,2,4]triazolo[4,3-
a]pyridin-7-yl)-1,2,4-oxadiazole (1m)
top
Crystal data top
C12H11N5O | F(000) = 504 |
Mr = 241.26 | Dx = 1.421 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 4.4041 (4) Å | Cell parameters from 1056 reflections |
b = 27.8787 (18) Å | θ = 4.3–23.3° |
c = 9.3533 (8) Å | µ = 0.10 mm−1 |
β = 100.816 (7)° | T = 293 K |
V = 1128.00 (16) Å3 | Stick, colourless |
Z = 4 | 0.20 × 0.05 × 0.05 mm |
Data collection top
Rigaku Xcalibur Sapphire3 diffractometer | 1981 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 1318 reflections with I > 2σ(I) |
Detector resolution: 16.1827 pixels mm-1 | Rint = 0.072 |
ω scans | θmax = 25.0°, θmin = 3.1° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2018) | h = −5→5 |
Tmin = 0.338, Tmax = 1.000 | k = −33→33 |
7951 measured reflections | l = −11→11 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.064 | H-atom parameters constrained |
wR(F2) = 0.196 | w = 1/[σ2(Fo2) + (0.0976P)2 + 0.2527P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
1981 reflections | Δρmax = 0.21 e Å−3 |
165 parameters | Δρmin = −0.25 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.2465 (4) | 0.51902 (7) | 0.6021 (2) | 0.0575 (6) | |
N4 | 0.6454 (5) | 0.53963 (8) | 0.7691 (2) | 0.0509 (6) | |
N3 | 0.1764 (5) | 0.69750 (8) | 0.5734 (2) | 0.0503 (6) | |
N5 | 0.3932 (6) | 0.47589 (8) | 0.6584 (3) | 0.0580 (7) | |
N1 | −0.2061 (6) | 0.68097 (10) | 0.3885 (3) | 0.0679 (8) | |
C4 | 0.3206 (6) | 0.60383 (9) | 0.6355 (3) | 0.0455 (7) | |
C8 | 0.6232 (6) | 0.49047 (9) | 0.7564 (3) | 0.0453 (7) | |
C7 | 0.4141 (6) | 0.55471 (9) | 0.6733 (3) | 0.0453 (7) | |
N2 | −0.1726 (6) | 0.73011 (10) | 0.4051 (3) | 0.0714 (8) | |
C5 | 0.0840 (6) | 0.61363 (10) | 0.5247 (3) | 0.0490 (7) | |
H5 | −0.026340 | 0.588920 | 0.471841 | 0.059* | |
C6 | 0.0074 (7) | 0.66178 (10) | 0.4909 (3) | 0.0525 (7) | |
C3 | 0.4849 (6) | 0.64155 (9) | 0.7185 (3) | 0.0530 (8) | |
H3 | 0.644608 | 0.634255 | 0.795511 | 0.064* | |
C9 | 0.8374 (6) | 0.45801 (10) | 0.8473 (3) | 0.0530 (7) | |
H9 | 1.047869 | 0.470463 | 0.877230 | 0.064* | |
C2 | 0.4123 (7) | 0.68739 (11) | 0.6870 (3) | 0.0556 (8) | |
H2 | 0.520150 | 0.712006 | 0.741409 | 0.067* | |
C11 | 0.7290 (7) | 0.42612 (11) | 0.9569 (3) | 0.0615 (8) | |
H11A | 0.867645 | 0.421110 | 1.049318 | 0.074* | |
H11B | 0.511197 | 0.426866 | 0.962166 | 0.074* | |
C10 | 0.8169 (8) | 0.40511 (11) | 0.8250 (3) | 0.0635 (8) | |
H10A | 0.652542 | 0.392945 | 0.749997 | 0.076* | |
H10B | 1.008809 | 0.387192 | 0.837105 | 0.076* | |
C1 | 0.0535 (8) | 0.73958 (10) | 0.5147 (3) | 0.0610 (8) | |
C12 | 0.1669 (9) | 0.78739 (11) | 0.5682 (4) | 0.0820 (11) | |
H12A | 0.142509 | 0.791116 | 0.667488 | 0.123* | |
H12B | 0.050458 | 0.811743 | 0.509355 | 0.123* | |
H12C | 0.381577 | 0.790363 | 0.562669 | 0.123* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0653 (12) | 0.0393 (11) | 0.0613 (13) | −0.0030 (9) | −0.0054 (10) | 0.0002 (9) |
N4 | 0.0515 (13) | 0.0403 (13) | 0.0570 (14) | 0.0019 (10) | 0.0002 (11) | −0.0041 (11) |
N3 | 0.0621 (14) | 0.0364 (13) | 0.0499 (13) | 0.0018 (10) | 0.0039 (11) | −0.0013 (10) |
N5 | 0.0662 (16) | 0.0411 (14) | 0.0618 (15) | −0.0014 (11) | −0.0006 (12) | 0.0041 (11) |
N1 | 0.0777 (18) | 0.0515 (16) | 0.0670 (17) | 0.0088 (13) | −0.0058 (14) | 0.0016 (13) |
C4 | 0.0500 (15) | 0.0382 (15) | 0.0468 (15) | 0.0007 (12) | 0.0050 (12) | 0.0001 (12) |
C8 | 0.0507 (15) | 0.0396 (15) | 0.0463 (15) | −0.0009 (12) | 0.0107 (12) | −0.0024 (12) |
C7 | 0.0502 (15) | 0.0391 (14) | 0.0457 (14) | −0.0047 (12) | 0.0065 (12) | −0.0039 (11) |
N2 | 0.087 (2) | 0.0515 (16) | 0.0689 (18) | 0.0139 (13) | −0.0033 (15) | 0.0080 (13) |
C5 | 0.0547 (16) | 0.0417 (15) | 0.0469 (15) | −0.0050 (12) | 0.0001 (12) | −0.0052 (12) |
C6 | 0.0566 (16) | 0.0488 (16) | 0.0495 (15) | 0.0015 (13) | 0.0031 (13) | −0.0001 (13) |
C3 | 0.0604 (17) | 0.0402 (15) | 0.0522 (17) | −0.0034 (13) | −0.0056 (13) | −0.0023 (12) |
C9 | 0.0481 (15) | 0.0434 (16) | 0.0658 (18) | 0.0019 (12) | 0.0062 (13) | 0.0030 (13) |
C2 | 0.0633 (18) | 0.0458 (17) | 0.0531 (17) | −0.0050 (13) | −0.0010 (13) | −0.0082 (13) |
C11 | 0.0599 (18) | 0.0624 (19) | 0.0591 (18) | 0.0052 (15) | 0.0030 (14) | 0.0108 (15) |
C10 | 0.077 (2) | 0.0443 (16) | 0.0671 (19) | 0.0076 (15) | 0.0083 (16) | −0.0011 (15) |
C1 | 0.077 (2) | 0.0433 (17) | 0.0605 (18) | 0.0122 (14) | 0.0078 (16) | 0.0050 (14) |
C12 | 0.116 (3) | 0.0384 (18) | 0.088 (3) | 0.0011 (18) | 0.011 (2) | −0.0021 (17) |
Geometric parameters (Å, º) top
O1—C7 | 1.339 (3) | C5—H5 | 0.9300 |
O1—N5 | 1.419 (3) | C3—C2 | 1.337 (4) |
N4—C7 | 1.294 (3) | C3—H3 | 0.9300 |
N4—C8 | 1.377 (3) | C9—C10 | 1.490 (4) |
N3—C1 | 1.363 (3) | C9—C11 | 1.501 (4) |
N3—C2 | 1.369 (4) | C9—H9 | 0.9800 |
N3—C6 | 1.388 (4) | C2—H2 | 0.9300 |
N5—C8 | 1.297 (4) | C11—C10 | 1.481 (4) |
N1—C6 | 1.322 (4) | C11—H11A | 0.9700 |
N1—N2 | 1.383 (4) | C11—H11B | 0.9700 |
C4—C5 | 1.352 (4) | C10—H10A | 0.9700 |
C4—C3 | 1.422 (4) | C10—H10B | 0.9700 |
C4—C7 | 1.454 (4) | C1—C12 | 1.477 (4) |
C8—C9 | 1.460 (4) | C12—H12A | 0.9600 |
N2—C1 | 1.315 (4) | C12—H12B | 0.9600 |
C5—C6 | 1.406 (4) | C12—H12C | 0.9600 |
| | | |
C7—O1—N5 | 106.0 (2) | C10—C9—C11 | 59.4 (2) |
C7—N4—C8 | 103.3 (2) | C8—C9—H9 | 114.8 |
C1—N3—C2 | 132.5 (3) | C10—C9—H9 | 114.8 |
C1—N3—C6 | 105.2 (2) | C11—C9—H9 | 114.8 |
C2—N3—C6 | 122.3 (2) | C3—C2—N3 | 118.9 (3) |
C8—N5—O1 | 103.7 (2) | C3—C2—H2 | 120.6 |
C6—N1—N2 | 105.9 (2) | N3—C2—H2 | 120.6 |
C5—C4—C3 | 120.6 (2) | C10—C11—C9 | 59.94 (19) |
C5—C4—C7 | 121.3 (2) | C10—C11—H11A | 117.8 |
C3—C4—C7 | 118.1 (2) | C9—C11—H11A | 117.8 |
N5—C8—N4 | 114.0 (2) | C10—C11—H11B | 117.8 |
N5—C8—C9 | 123.4 (2) | C9—C11—H11B | 117.8 |
N4—C8—C9 | 122.6 (2) | H11A—C11—H11B | 114.9 |
N4—C7—O1 | 113.1 (2) | C11—C10—C9 | 60.7 (2) |
N4—C7—C4 | 128.7 (2) | C11—C10—H10A | 117.7 |
O1—C7—C4 | 118.3 (2) | C9—C10—H10A | 117.7 |
C1—N2—N1 | 109.6 (2) | C11—C10—H10B | 117.7 |
C4—C5—C6 | 118.9 (2) | C9—C10—H10B | 117.7 |
C4—C5—H5 | 120.5 | H10A—C10—H10B | 114.8 |
C6—C5—H5 | 120.5 | N2—C1—N3 | 109.0 (3) |
N1—C6—N3 | 110.3 (3) | N2—C1—C12 | 127.1 (3) |
N1—C6—C5 | 131.1 (3) | N3—C1—C12 | 123.8 (3) |
N3—C6—C5 | 118.6 (2) | C1—C12—H12A | 109.5 |
C2—C3—C4 | 120.7 (3) | C1—C12—H12B | 109.5 |
C2—C3—H3 | 119.6 | H12A—C12—H12B | 109.5 |
C4—C3—H3 | 119.6 | C1—C12—H12C | 109.5 |
C8—C9—C10 | 121.1 (3) | H12A—C12—H12C | 109.5 |
C8—C9—C11 | 120.8 (2) | H12B—C12—H12C | 109.5 |
| | | |
C7—O1—N5—C8 | 1.1 (3) | C2—N3—C6—C5 | −0.6 (4) |
O1—N5—C8—N4 | −0.8 (3) | C4—C5—C6—N1 | 178.8 (3) |
O1—N5—C8—C9 | 178.2 (2) | C4—C5—C6—N3 | −0.5 (4) |
C7—N4—C8—N5 | 0.2 (3) | C5—C4—C3—C2 | −1.2 (4) |
C7—N4—C8—C9 | −178.7 (2) | C7—C4—C3—C2 | 178.9 (3) |
C8—N4—C7—O1 | 0.5 (3) | N5—C8—C9—C10 | 4.5 (4) |
C8—N4—C7—C4 | −179.2 (3) | N4—C8—C9—C10 | −176.6 (2) |
N5—O1—C7—N4 | −1.0 (3) | N5—C8—C9—C11 | −66.0 (4) |
N5—O1—C7—C4 | 178.7 (2) | N4—C8—C9—C11 | 112.9 (3) |
C5—C4—C7—N4 | 175.2 (3) | C4—C3—C2—N3 | 0.1 (4) |
C3—C4—C7—N4 | −4.9 (4) | C1—N3—C2—C3 | −179.0 (3) |
C5—C4—C7—O1 | −4.4 (4) | C6—N3—C2—C3 | 0.9 (4) |
C3—C4—C7—O1 | 175.4 (2) | C8—C9—C11—C10 | 110.2 (3) |
C6—N1—N2—C1 | −0.3 (4) | C8—C9—C10—C11 | −109.7 (3) |
C3—C4—C5—C6 | 1.4 (4) | N1—N2—C1—N3 | 0.2 (4) |
C7—C4—C5—C6 | −178.7 (2) | N1—N2—C1—C12 | 179.4 (3) |
N2—N1—C6—N3 | 0.3 (3) | C2—N3—C1—N2 | 179.9 (3) |
N2—N1—C6—C5 | −179.1 (3) | C6—N3—C1—N2 | 0.0 (3) |
C1—N3—C6—N1 | −0.2 (3) | C2—N3—C1—C12 | 0.6 (5) |
C2—N3—C6—N1 | 179.9 (3) | C6—N3—C1—C12 | −179.2 (3) |
C1—N3—C6—C5 | 179.3 (2) | | |
3-Cyclopropyl-5-(3-methyl-[1,2,4]triazolo[4,3-
a]pyridin-7-yl)-1,2,4-oxadiazole (1r)
top
Crystal data top
C12H11N5O | Dx = 1.411 Mg m−3 |
Mr = 241.26 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 1390 reflections |
a = 12.2191 (13) Å | θ = 4.0–22.0° |
b = 8.1593 (9) Å | µ = 0.10 mm−1 |
c = 22.788 (2) Å | T = 293 K |
V = 2271.9 (4) Å3 | Stick, colourless |
Z = 8 | 0.20 × 0.05 × 0.05 mm |
F(000) = 1008 | |
Data collection top
Rigaku Xcalibur Sapphire3 diffractometer | 2002 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 1311 reflections with I > 2σ(I) |
Detector resolution: 16.1827 pixels mm-1 | Rint = 0.095 |
ω scans | θmax = 25.0°, θmin = 3.1° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2018) | h = −14→14 |
Tmin = 0.228, Tmax = 1.000 | k = −9→9 |
15782 measured reflections | l = −27→27 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.054 | H-atom parameters constrained |
wR(F2) = 0.158 | w = 1/[σ2(Fo2) + (0.0721P)2 + 0.052P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
2002 reflections | Δρmax = 0.15 e Å−3 |
164 parameters | Δρmin = −0.17 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.88986 (12) | 0.5205 (2) | 0.52200 (8) | 0.0715 (5) | |
N3 | 0.80711 (15) | 0.2052 (2) | 0.70333 (9) | 0.0606 (5) | |
N4 | 0.71113 (15) | 0.5058 (2) | 0.51527 (9) | 0.0617 (6) | |
N5 | 0.86045 (17) | 0.6039 (2) | 0.46946 (10) | 0.0726 (6) | |
N1 | 0.62777 (18) | 0.1981 (3) | 0.71423 (11) | 0.0839 (7) | |
N2 | 0.6767 (2) | 0.1183 (3) | 0.76098 (11) | 0.0848 (7) | |
C7 | 0.79654 (18) | 0.4670 (3) | 0.54524 (11) | 0.0573 (6) | |
C4 | 0.80063 (17) | 0.3756 (3) | 0.60016 (10) | 0.0566 (6) | |
C8 | 0.75456 (19) | 0.5904 (3) | 0.46866 (11) | 0.0601 (6) | |
C2 | 0.90468 (18) | 0.2421 (3) | 0.67606 (11) | 0.0648 (7) | |
H2 | 0.971001 | 0.209978 | 0.692458 | 0.078* | |
C3 | 0.90181 (18) | 0.3253 (3) | 0.62528 (11) | 0.0638 (7) | |
H3 | 0.966972 | 0.350475 | 0.606212 | 0.077* | |
C6 | 0.70786 (19) | 0.2498 (3) | 0.67980 (12) | 0.0638 (7) | |
C5 | 0.70492 (18) | 0.3374 (3) | 0.62699 (11) | 0.0624 (7) | |
H5 | 0.638458 | 0.368828 | 0.610597 | 0.075* | |
C9 | 0.68851 (19) | 0.6572 (3) | 0.42135 (11) | 0.0670 (7) | |
H9 | 0.727228 | 0.725505 | 0.392691 | 0.080* | |
C1 | 0.7831 (2) | 0.1236 (3) | 0.75449 (12) | 0.0699 (7) | |
C11 | 0.5717 (2) | 0.7022 (3) | 0.43306 (12) | 0.0756 (8) | |
H11A | 0.544027 | 0.685885 | 0.472521 | 0.091* | |
H11B | 0.542301 | 0.797114 | 0.412884 | 0.091* | |
C10 | 0.5957 (2) | 0.5555 (3) | 0.39780 (12) | 0.0797 (8) | |
H10A | 0.581175 | 0.560604 | 0.355993 | 0.096* | |
H10B | 0.582901 | 0.449340 | 0.415649 | 0.096* | |
C12 | 0.8657 (2) | 0.0530 (3) | 0.79399 (12) | 0.0854 (8) | |
H12A | 0.904585 | −0.032585 | 0.773953 | 0.128* | |
H12B | 0.830322 | 0.008629 | 0.828076 | 0.128* | |
H12C | 0.916277 | 0.136905 | 0.805742 | 0.128* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0400 (10) | 0.0864 (11) | 0.0881 (12) | −0.0041 (8) | 0.0008 (8) | 0.0039 (9) |
N3 | 0.0425 (12) | 0.0646 (11) | 0.0746 (13) | −0.0054 (8) | 0.0040 (10) | −0.0144 (10) |
N4 | 0.0415 (12) | 0.0710 (12) | 0.0726 (13) | −0.0028 (9) | 0.0005 (10) | −0.0114 (10) |
N5 | 0.0469 (13) | 0.0832 (14) | 0.0877 (15) | 0.0008 (10) | 0.0023 (11) | 0.0083 (12) |
N1 | 0.0537 (15) | 0.1047 (17) | 0.0934 (17) | −0.0082 (12) | 0.0101 (12) | −0.0026 (14) |
N2 | 0.0638 (16) | 0.1004 (17) | 0.0902 (17) | −0.0112 (13) | 0.0103 (13) | 0.0011 (14) |
C7 | 0.0374 (14) | 0.0596 (13) | 0.0749 (16) | −0.0028 (10) | 0.0020 (11) | −0.0192 (12) |
C4 | 0.0405 (14) | 0.0606 (13) | 0.0686 (15) | −0.0020 (10) | 0.0009 (10) | −0.0188 (11) |
C8 | 0.0457 (15) | 0.0593 (13) | 0.0753 (16) | 0.0005 (10) | 0.0029 (12) | −0.0149 (12) |
C2 | 0.0374 (14) | 0.0764 (15) | 0.0807 (17) | −0.0004 (11) | 0.0013 (12) | −0.0113 (14) |
C3 | 0.0382 (14) | 0.0773 (15) | 0.0759 (17) | −0.0042 (10) | 0.0047 (11) | −0.0103 (13) |
C6 | 0.0389 (15) | 0.0723 (15) | 0.0802 (17) | −0.0049 (11) | 0.0088 (12) | −0.0159 (13) |
C5 | 0.0380 (14) | 0.0737 (15) | 0.0757 (17) | −0.0024 (10) | −0.0002 (11) | −0.0177 (13) |
C9 | 0.0491 (16) | 0.0733 (15) | 0.0786 (17) | 0.0022 (11) | 0.0010 (12) | −0.0040 (13) |
C1 | 0.0616 (18) | 0.0697 (16) | 0.0783 (17) | −0.0093 (13) | 0.0086 (14) | −0.0093 (13) |
C11 | 0.0557 (17) | 0.0889 (18) | 0.0822 (17) | 0.0112 (13) | −0.0028 (13) | −0.0073 (14) |
C10 | 0.0664 (18) | 0.0893 (18) | 0.0835 (18) | −0.0024 (13) | −0.0116 (14) | −0.0148 (15) |
C12 | 0.078 (2) | 0.0953 (19) | 0.0828 (19) | −0.0041 (15) | −0.0018 (15) | 0.0021 (16) |
Geometric parameters (Å, º) top
O1—C7 | 1.331 (3) | C2—H2 | 0.9300 |
O1—N5 | 1.423 (3) | C3—H3 | 0.9300 |
N3—C1 | 1.375 (3) | C6—C5 | 1.400 (3) |
N3—C6 | 1.375 (3) | C5—H5 | 0.9300 |
N3—C2 | 1.378 (3) | C9—C11 | 1.497 (3) |
N4—C7 | 1.287 (3) | C9—C10 | 1.504 (3) |
N4—C8 | 1.373 (3) | C9—H9 | 0.9800 |
N5—C8 | 1.299 (3) | C1—C12 | 1.470 (4) |
N1—C6 | 1.323 (3) | C11—C10 | 1.471 (3) |
N1—N2 | 1.384 (3) | C11—H11A | 0.9700 |
N2—C1 | 1.309 (3) | C11—H11B | 0.9700 |
C7—C4 | 1.457 (3) | C10—H10A | 0.9700 |
C4—C5 | 1.356 (3) | C10—H10B | 0.9700 |
C4—C3 | 1.423 (3) | C12—H12A | 0.9600 |
C8—C9 | 1.453 (3) | C12—H12B | 0.9600 |
C2—C3 | 1.342 (3) | C12—H12C | 0.9600 |
| | | |
C7—O1—N5 | 105.98 (17) | C6—C5—H5 | 120.6 |
C1—N3—C6 | 105.7 (2) | C8—C9—C11 | 119.3 (2) |
C1—N3—C2 | 132.3 (2) | C8—C9—C10 | 118.4 (2) |
C6—N3—C2 | 122.0 (2) | C11—C9—C10 | 58.70 (16) |
C7—N4—C8 | 102.8 (2) | C8—C9—H9 | 116.1 |
C8—N5—O1 | 102.86 (18) | C11—C9—H9 | 116.1 |
C6—N1—N2 | 106.7 (2) | C10—C9—H9 | 116.1 |
C1—N2—N1 | 109.1 (2) | N2—C1—N3 | 108.9 (2) |
N4—C7—O1 | 113.7 (2) | N2—C1—C12 | 126.9 (3) |
N4—C7—C4 | 127.5 (2) | N3—C1—C12 | 124.2 (2) |
O1—C7—C4 | 118.7 (2) | C10—C11—C9 | 60.88 (17) |
C5—C4—C3 | 120.1 (2) | C10—C11—H11A | 117.7 |
C5—C4—C7 | 118.4 (2) | C9—C11—H11A | 117.7 |
C3—C4—C7 | 121.5 (2) | C10—C11—H11B | 117.7 |
N5—C8—N4 | 114.7 (2) | C9—C11—H11B | 117.7 |
N5—C8—C9 | 122.1 (2) | H11A—C11—H11B | 114.8 |
N4—C8—C9 | 123.2 (2) | C11—C10—C9 | 60.42 (16) |
C3—C2—N3 | 118.5 (2) | C11—C10—H10A | 117.7 |
C3—C2—H2 | 120.8 | C9—C10—H10A | 117.7 |
N3—C2—H2 | 120.8 | C11—C10—H10B | 117.7 |
C2—C3—C4 | 121.0 (2) | C9—C10—H10B | 117.7 |
C2—C3—H3 | 119.5 | H10A—C10—H10B | 114.8 |
C4—C3—H3 | 119.5 | C1—C12—H12A | 109.5 |
N1—C6—N3 | 109.7 (2) | C1—C12—H12B | 109.5 |
N1—C6—C5 | 130.8 (2) | H12A—C12—H12B | 109.5 |
N3—C6—C5 | 119.5 (2) | C1—C12—H12C | 109.5 |
C4—C5—C6 | 118.9 (2) | H12A—C12—H12C | 109.5 |
C4—C5—H5 | 120.6 | H12B—C12—H12C | 109.5 |
| | | |
C7—O1—N5—C8 | 0.5 (2) | C1—N3—C6—N1 | −0.2 (3) |
C6—N1—N2—C1 | 0.4 (3) | C2—N3—C6—N1 | 179.29 (19) |
C8—N4—C7—O1 | 0.5 (2) | C1—N3—C6—C5 | 179.48 (19) |
C8—N4—C7—C4 | 179.8 (2) | C2—N3—C6—C5 | −1.0 (3) |
N5—O1—C7—N4 | −0.7 (2) | C3—C4—C5—C6 | 0.7 (3) |
N5—O1—C7—C4 | 180.00 (17) | C7—C4—C5—C6 | −179.95 (19) |
N4—C7—C4—C5 | −6.5 (3) | N1—C6—C5—C4 | 179.9 (2) |
O1—C7—C4—C5 | 172.71 (19) | N3—C6—C5—C4 | 0.3 (3) |
N4—C7—C4—C3 | 172.8 (2) | N5—C8—C9—C11 | −154.4 (2) |
O1—C7—C4—C3 | −8.0 (3) | N4—C8—C9—C11 | 26.8 (3) |
O1—N5—C8—N4 | −0.2 (2) | N5—C8—C9—C10 | 137.6 (2) |
O1—N5—C8—C9 | −179.14 (19) | N4—C8—C9—C10 | −41.2 (3) |
C7—N4—C8—N5 | −0.1 (2) | N1—N2—C1—N3 | −0.5 (3) |
C7—N4—C8—C9 | 178.7 (2) | N1—N2—C1—C12 | −179.7 (2) |
C1—N3—C2—C3 | −180.0 (2) | C6—N3—C1—N2 | 0.5 (3) |
C6—N3—C2—C3 | 0.6 (3) | C2—N3—C1—N2 | −179.0 (2) |
N3—C2—C3—C4 | 0.4 (3) | C6—N3—C1—C12 | 179.6 (2) |
C5—C4—C3—C2 | −1.1 (3) | C2—N3—C1—C12 | 0.2 (4) |
C7—C4—C3—C2 | 179.6 (2) | C8—C9—C11—C10 | −107.3 (3) |
N2—N1—C6—N3 | −0.1 (3) | C8—C9—C10—C11 | 108.8 (3) |
N2—N1—C6—C5 | −179.7 (2) | | |
Selected geometric parameters for molecule 1 in monoclinic and
orthorhombic polymorphic crystals topParameter | Structure 1m | Structure 1r |
Bond length (Å) | | |
C4—C7 | 1.454 (4) | 1.457 (3) |
C8—C9 | 1.460 (4) | 1.453 (3) |
| | |
Torsion angle (°) | | |
C5—C4—C7—O1 | -4.5 (4) | 172.7 (2) |
N4—C8—C9—H9 | -31.6 | 173.5 |
Geometric characteristics (Å, °) of the intermolecular hydrogen bonds,
stacking interactions and intermolecular short contacts in different
polymorphic crystals of compound 1 topInteraction | Symmetry operation | Geometric characteristics | |
| | H···A | D—H···A |
Polymorph 1m | | | |
C5—H5···N5 | -x ,-y+1, -z+1 | 2.57 | 172 |
C2—H2···N2 | x+1, -y+3/2, z+1/2 | 2.45 | 174 |
C11—H11a···N4 | -x+2, -y+1, -z+2 | 2.71 | 143 |
Stacking `head-to-head' | x-1, y, z | Distance between mean planes is 3.38 Å
Plane-to-plane shift is 2.820 Å
Plane-to-plane twist angle is 0.0° | |
O1···O1' | -x, -y+2, -z+1 | 2.82 | |
| | | |
Polymorph 1r | | | |
C3—H3···N5 | -x+2, -y+1, -z+1 | 2.75 | 168 |
C12—H12a···N1(π) | -x+3/2, y-1/2, z | 2.62 | 142 |
C12—H12c···N1(lp) | x+1/2, y, -z+3/2 | 2.67 | 135 |
Stacking `head-to-tail' | -x+3/2, y-1/2, z | Distance between mean planes is 3.50 Å
Plane-to-plane shift is 2.224 Å
Plane-to-plane twist angle is 2.5° | |
Stacking `head-to-tail' | -x+3/2, y+1/2, z | Distance between mean planes is 3.52 Å
Plane-to-plane shift is 2.196 Å
Plane-to-plane twist angle is 2.5° | |
O1···O1' | -x+2, -y+1, -z+1 | 2.89 | |
Symmetry codes, interaction energies of the basic molecule with neighbouring
ones (Eint, kcal mol-1), with the highest values (more than 5% of
total interaction energy) and the contribution of this energy to the total
interaction energy (%) in polymorphic crystals 1m (for full list of dimers,
see Table S1 in the supporting information) topDimer | Symmetry operation | Eint (kcal mol-1) | Contribution to the total interaction energy (%) | Type of interaction |
1m_d1 | x-1, y, z | -9.35 | 14.2 | Stacking `head-to-head' |
1m_d2 | x+1, y, z | -9.35 | 14.2 | Stacking `head-to-head' |
1m_d3 | -x+1, -y+1, -z+1 | -8.68 | 13.2 | dispersion |
1m_d4 | -x, -y+1, -z+1 | -6.75 | 10.3 | Car—H···N |
1m_d5 | x+1, -y+3/2, z+1/2 | -6.59 | 10.0 | Car—H···N |
1m_d6 | x-1, -y+3/2, z-1/2 | -6.59 | 10.0 | Car—H···N |
1m_d7 | -x+2, -y+1, -z+2 | -5.08 | 7.7 | Csp3(propyl)—H···N |
1m_d8 | -x+1, -y+1, -z+2 | -4.86 | 7.4 | dispersion |
Symmetry codes, interaction energies of the basic molecule with neighbouring
ones (Eint, kcal mol-1) with the highest values (more than 5% of
total interaction energy) and the contribution of this energy to the total
interaction energy (%) in polymorphic crystals 1r (for full list of dimers,
see Table S2 in the supporting information) topDimer | Symmetry operation | Eint (kcal mol-1) | Contribution to the total interaction energy (%) | Type of interaction |
1r_d1 | -x+3/2, y-1/2, z | -16.61 | 22.8 | Stacking `head-to-tail' |
1r_d2 | -x+3/2, y+1/2, z | -16.61 | 22.8 | Stacking `head-to-tail' |
1r_d3 | -x+1, -y+1, -z+1 | -6.93 | 9.5 | dispersion |
1r_d4 | x-1/2, y, -z+3/2 | -6.32 | 8.7 | Csp3—H···N |
1r_d5 | x+1/2, y, -z+3/2 | -6.32 | 8.7 | Csp3—H···N |
1r_d6 | -x+2, -y+1, -z+1 | -3.92 | 5.4 | Car—H···N |