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Six new py­rimi­din-2-yl-substituted tri­aryl­tri­az­oles, namely, 4-(4-R-phen­yl)-3-(pyri­din-2-yl)-5-(py­rimi­din-2-yl)-1,2,4-tri­az­oles [L1: R = meth­oxy (OCH3); L2: R = methyl (CH3); L3: R = nil (H); L4: R = bromo (Br); L5: R = chloro (Cl); L6: R = fluoro (F)] have been successfully synthesized with yields in the range 68.3–81.7%. Com­pounds L1–6 have been characterized by UV–Vis, FT–IR, 1H NMR and ESI–MS spectroscopy, and elemental analysis. In addition, the structures of L2–6 and the ethanol mono­solvate of L2 (L2·C2H5OH) have been determined by single-crystal X-ray dif­frac­tion. A combination of inter­molecular O—H...N, C—H...O, C—H...N and C—H...π hydrogen bonds connects the components of L2·C2H5OH into a three-dimensional (3D) framework. A combination of three inter­molecular C—H...N hydrogen bonds links the mol­ecules of L2 or L3 into two dif­ferent 3D networks. Both L4 and L5 show a similar 3D net structure through two inter­molecular C—H...N hydrogen bonds and one kind of C—H...π inter­action. However, L6 displays a more complicated 3D net structure via three inter­molecular C—H...N hydrogen bonds and one kind of C—H...π inter­action. Notably, an inter­action between the π-electrons and the lone-pair p-electrons of a halogen atom (Br, Cl and F) is observed in L4–6, which will further stabilize the 3D networks. The inter­molecular inter­actions in L2·C2H5OH and L2–6 were further investigated by 3D Hirshfeld surface analyses and 2D fingerprint plots to show that the prominent inter­actions are H...H, N...H/H...N and C...H/H...C contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229624002018/vp3032sup1.cif
Contains datablocks L2.C2H5OH, L3, L4, L5, L6, L2_auto, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229624002018/vp3032L2.C2H5OHsup2.hkl
Contains datablock L2.C2H5OH

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229624002018/vp3032L3sup3.hkl
Contains datablock L3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229624002018/vp3032L4sup4.hkl
Contains datablock L4

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229624002018/vp3032L5sup5.hkl
Contains datablock L5

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229624002018/vp3032L6sup6.hkl
Contains datablock L6

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229624002018/vp3032L2_autosup7.hkl
Contains datablock L2_auto

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229624002018/vp3032L2.C2H5OHsup8.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229624002018/vp3032L3sup9.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229624002018/vp3032L4sup10.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229624002018/vp3032L5sup11.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229624002018/vp3032L6sup12.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229624002018/vp3032L2_autosup13.cml
Supplementary material

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229624002018/vp3032sup14.pdf
Additional figures

CCDC references: 2336435; 2336434; 2336433; 2336432; 2336431; 2336430

Computing details top

4-(4-Methylphenyl)-3-(pyridin-2-yl)-5-(pyrimidin-2-yl)-1,2,4-triazole ethanol monosolvate (L2.C2H5OH) top
Crystal data top
C18H14N6·C2H6OZ = 2
Mr = 360.42F(000) = 380
Triclinic, P1Dx = 1.277 Mg m3
a = 9.455 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.628 (8) ÅCell parameters from 1462 reflections
c = 12.023 (10) Åθ = 2.4–21.7°
α = 69.506 (10)°µ = 0.08 mm1
β = 79.904 (12)°T = 293 K
γ = 66.215 (11)°Block, clear light colourless
V = 937.3 (13) Å30.19 × 0.15 × 0.11 mm
Data collection top
Bruker APEXII CCD area detector
diffractometer
2042 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
phi and ω scansθmax = 25.1°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1111
Tmin = 0.984, Tmax = 0.991k = 1111
6792 measured reflectionsl = 1314
3305 independent reflections
Refinement top
Refinement on F2Primary atom site location: iterative
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.063H-atom parameters constrained
wR(F2) = 0.197 w = 1/[σ2(Fo2) + (0.1138P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
3305 reflectionsΔρmax = 0.54 e Å3
247 parametersΔρmin = 0.31 e Å3
13 restraints
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
xyzUiso*/Ueq
N10.9353 (3)0.2070 (3)0.8372 (2)0.0721 (8)
N20.8502 (3)0.3247 (3)0.5367 (2)0.0565 (7)
N30.7357 (3)0.3032 (3)0.49514 (19)0.0558 (7)
N40.6887 (2)0.2718 (2)0.68607 (17)0.0424 (6)
N50.4824 (3)0.1168 (3)0.6702 (2)0.0570 (7)
N60.4419 (3)0.2999 (3)0.4735 (2)0.0604 (7)
C11.0356 (5)0.2029 (5)0.9042 (3)0.0923 (13)
H11.0476730.1323400.9811060.111*
C21.1231 (4)0.2976 (5)0.8658 (4)0.0908 (12)
H21.1922040.2907090.9156960.109*
C31.1062 (4)0.4001 (4)0.7547 (4)0.0779 (10)
H31.1639030.4650350.7267200.093*
C41.0038 (3)0.4084 (4)0.6830 (3)0.0591 (8)
H40.9901500.4791940.6061410.071*
C50.9216 (3)0.3097 (3)0.7270 (3)0.0519 (7)
C60.8202 (3)0.3051 (3)0.6501 (2)0.0465 (7)
C70.6405 (3)0.2726 (3)0.5852 (2)0.0451 (7)
C80.5107 (3)0.2293 (3)0.5769 (2)0.0454 (7)
C90.3336 (4)0.2493 (4)0.4644 (3)0.0678 (9)
H90.2821120.2943330.3936820.081*
C100.2944 (3)0.1352 (4)0.5532 (3)0.0663 (9)
H100.2187940.1015120.5442820.080*
C110.3715 (3)0.0727 (4)0.6558 (3)0.0670 (9)
H110.3457710.0039710.7186140.080*
C120.5992 (3)0.2806 (3)0.7965 (2)0.0409 (6)
C130.6242 (3)0.1473 (4)0.8948 (2)0.0576 (8)
H130.6949400.0483440.8905970.069*
C140.5430 (4)0.1625 (4)0.9996 (2)0.0645 (9)
H140.5598070.0725101.0661720.077*
C150.4374 (4)0.3076 (4)1.0082 (2)0.0571 (8)
C160.4129 (3)0.4379 (4)0.9081 (3)0.0585 (8)
H160.3403270.5364960.9114200.070*
C170.4947 (3)0.4252 (3)0.8015 (2)0.0496 (7)
H170.4780210.5147110.7344840.060*
C180.3492 (5)0.3233 (5)1.1240 (3)0.0936 (13)
H18A0.2951290.2510331.1512000.140*
H18B0.2762360.4307901.1116960.140*
H18C0.4204070.2979861.1825790.140*
O10.7849 (3)0.1999 (4)0.2878 (2)0.0960 (8)
H1A0.7724210.2352210.3431890.144*
C191.0594 (5)0.1292 (6)0.3210 (5)0.1319 (18)
H19A1.1578120.1009200.2791310.198*
H19B1.0590190.0416730.3909430.198*
H19C1.0413880.2214200.3435450.198*
C200.9376 (6)0.1648 (7)0.2443 (4)0.1362 (19)
H20A0.9399530.2547380.1755370.163*
H20B0.9656450.0741290.2158270.163*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0834 (18)0.086 (2)0.0587 (16)0.0527 (16)0.0174 (14)0.0042 (15)
N20.0560 (14)0.0713 (17)0.0470 (14)0.0316 (13)0.0061 (11)0.0184 (12)
N30.0571 (14)0.0705 (17)0.0421 (13)0.0289 (13)0.0043 (11)0.0171 (12)
N40.0463 (12)0.0467 (13)0.0348 (11)0.0210 (10)0.0006 (9)0.0093 (10)
N50.0610 (14)0.0710 (17)0.0456 (14)0.0367 (13)0.0063 (11)0.0093 (12)
N60.0627 (15)0.0678 (17)0.0459 (14)0.0200 (13)0.0166 (12)0.0101 (12)
C10.107 (3)0.120 (3)0.070 (2)0.068 (3)0.032 (2)0.008 (2)
C20.078 (2)0.112 (3)0.107 (3)0.053 (2)0.020 (2)0.035 (3)
C30.064 (2)0.076 (3)0.110 (3)0.0412 (19)0.001 (2)0.031 (2)
C40.0516 (16)0.0555 (19)0.074 (2)0.0276 (15)0.0051 (15)0.0186 (16)
C50.0457 (15)0.0542 (18)0.0591 (18)0.0208 (14)0.0017 (13)0.0205 (15)
C60.0452 (15)0.0500 (17)0.0449 (16)0.0216 (13)0.0024 (12)0.0127 (13)
C70.0491 (15)0.0501 (17)0.0362 (14)0.0192 (13)0.0001 (12)0.0134 (12)
C80.0449 (14)0.0528 (17)0.0371 (14)0.0155 (13)0.0002 (11)0.0160 (13)
C90.0621 (19)0.086 (3)0.0533 (19)0.0206 (18)0.0179 (15)0.0197 (18)
C100.0542 (18)0.089 (2)0.069 (2)0.0317 (17)0.0082 (16)0.0312 (19)
C110.0652 (19)0.085 (2)0.0576 (19)0.0400 (18)0.0040 (15)0.0150 (17)
C120.0442 (14)0.0494 (17)0.0329 (13)0.0239 (13)0.0047 (11)0.0080 (12)
C130.0710 (19)0.0512 (18)0.0466 (17)0.0236 (15)0.0035 (14)0.0088 (14)
C140.090 (2)0.073 (2)0.0361 (16)0.047 (2)0.0000 (15)0.0041 (15)
C150.0671 (19)0.084 (2)0.0418 (16)0.0509 (19)0.0093 (14)0.0231 (16)
C160.0587 (17)0.067 (2)0.0561 (18)0.0283 (16)0.0104 (14)0.0271 (16)
C170.0525 (16)0.0537 (19)0.0440 (16)0.0238 (15)0.0003 (12)0.0129 (13)
C180.119 (3)0.136 (4)0.056 (2)0.079 (3)0.034 (2)0.045 (2)
O10.0978 (19)0.117 (2)0.0848 (19)0.0393 (17)0.0047 (15)0.0490 (17)
C190.104 (3)0.131 (3)0.149 (4)0.030 (3)0.016 (3)0.056 (3)
C200.141 (4)0.147 (4)0.123 (3)0.027 (3)0.010 (3)0.083 (3)
Geometric parameters (Å, º) top
N1—C11.329 (4)C10—C111.363 (4)
N1—C51.337 (4)C11—H110.9300
N2—N31.381 (3)C12—C131.375 (4)
N2—C61.304 (3)C12—C171.359 (4)
N3—C71.311 (3)C13—H130.9300
N4—C61.369 (3)C13—C141.377 (4)
N4—C71.365 (3)C14—H140.9300
N4—C121.453 (3)C14—C151.379 (4)
N5—C81.334 (3)C15—C161.372 (4)
N5—C111.335 (4)C15—C181.515 (4)
N6—C81.329 (3)C16—H160.9300
N6—C91.333 (4)C16—C171.394 (4)
C1—H10.9300C17—H170.9300
C1—C21.382 (5)C18—H18A0.9600
C2—H20.9300C18—H18B0.9600
C2—C31.345 (5)C18—H18C0.9600
C3—H30.9300O1—H1A0.8200
C3—C41.367 (5)O1—C201.392 (5)
C4—H40.9300C19—H19A0.9600
C4—C51.373 (4)C19—H19B0.9600
C5—C61.467 (4)C19—H19C0.9600
C7—C81.475 (4)C19—C201.458 (4)
C9—H90.9300C20—H20A0.9700
C9—C101.361 (4)C20—H20B0.9700
C10—H100.9300
C1—N1—C5116.3 (3)N5—C11—H11118.5
C6—N2—N3107.1 (2)C10—C11—H11118.5
C7—N3—N2107.5 (2)C13—C12—N4120.8 (2)
C6—N4—C12126.3 (2)C17—C12—N4118.2 (2)
C7—N4—C6104.3 (2)C17—C12—C13120.9 (3)
C7—N4—C12127.2 (2)C12—C13—H13120.5
C8—N5—C11115.0 (2)C12—C13—C14119.0 (3)
C8—N6—C9114.6 (3)C14—C13—H13120.5
N1—C1—H1118.2C13—C14—H14119.2
N1—C1—C2123.6 (4)C13—C14—C15121.7 (3)
C2—C1—H1118.2C15—C14—H14119.2
C1—C2—H2120.7C14—C15—C18121.3 (3)
C3—C2—C1118.5 (3)C16—C15—C14118.0 (3)
C3—C2—H2120.7C16—C15—C18120.7 (3)
C2—C3—H3120.2C15—C16—H16119.4
C2—C3—C4119.7 (3)C15—C16—C17121.2 (3)
C4—C3—H3120.2C17—C16—H16119.4
C3—C4—H4120.8C12—C17—C16119.3 (3)
C3—C4—C5118.5 (3)C12—C17—H17120.4
C5—C4—H4120.8C16—C17—H17120.4
N1—C5—C4123.3 (3)C15—C18—H18A109.5
N1—C5—C6116.3 (3)C15—C18—H18B109.5
C4—C5—C6120.2 (3)C15—C18—H18C109.5
N2—C6—N4110.8 (2)H18A—C18—H18B109.5
N2—C6—C5123.2 (2)H18A—C18—H18C109.5
N4—C6—C5125.9 (2)H18B—C18—H18C109.5
N3—C7—N4110.3 (2)C20—O1—H1A109.5
N3—C7—C8123.0 (2)H19A—C19—H19B109.5
N4—C7—C8126.4 (2)H19A—C19—H19C109.5
N5—C8—C7116.8 (2)H19B—C19—H19C109.5
N6—C8—N5127.4 (3)C20—C19—H19A109.5
N6—C8—C7115.6 (2)C20—C19—H19B109.5
N6—C9—H9118.3C20—C19—H19C109.5
N6—C9—C10123.5 (3)O1—C20—C19120.2 (4)
C10—C9—H9118.3O1—C20—H20A107.3
C9—C10—H10121.7O1—C20—H20B107.3
C9—C10—C11116.6 (3)C19—C20—H20A107.3
C11—C10—H10121.7C19—C20—H20B107.3
N5—C11—C10122.9 (3)H20A—C20—H20B106.9
N1—C1—C2—C30.1 (6)C6—N4—C12—C1394.6 (3)
N1—C5—C6—N2142.7 (3)C6—N4—C12—C1782.7 (3)
N1—C5—C6—N433.4 (4)C7—N4—C6—N20.0 (3)
N2—N3—C7—N40.5 (3)C7—N4—C6—C5176.6 (3)
N2—N3—C7—C8174.6 (2)C7—N4—C12—C13104.9 (3)
N3—N2—C6—N40.3 (3)C7—N4—C12—C1777.8 (3)
N3—N2—C6—C5176.4 (2)C8—N5—C11—C101.2 (5)
N3—C7—C8—N5140.8 (3)C8—N6—C9—C100.3 (4)
N3—C7—C8—N634.7 (4)C9—N6—C8—N50.4 (4)
N4—C7—C8—N532.3 (4)C9—N6—C8—C7174.6 (2)
N4—C7—C8—N6152.1 (3)C9—C10—C11—N51.2 (5)
N4—C12—C13—C14176.4 (2)C11—N5—C8—N60.3 (4)
N4—C12—C17—C16177.0 (2)C11—N5—C8—C7175.3 (2)
N6—C9—C10—C110.5 (5)C12—N4—C6—N2164.1 (2)
C1—N1—C5—C40.6 (5)C12—N4—C6—C519.3 (4)
C1—N1—C5—C6175.3 (3)C12—N4—C7—N3164.2 (2)
C1—C2—C3—C40.1 (6)C12—N4—C7—C821.9 (4)
C2—C3—C4—C50.5 (5)C12—C13—C14—C150.1 (4)
C3—C4—C5—N10.8 (5)C13—C12—C17—C160.4 (4)
C3—C4—C5—C6174.9 (3)C13—C14—C15—C161.1 (4)
C4—C5—C6—N233.3 (4)C13—C14—C15—C18179.7 (3)
C4—C5—C6—N4150.5 (3)C14—C15—C16—C171.6 (4)
C5—N1—C1—C20.2 (6)C15—C16—C17—C120.9 (4)
C6—N2—N3—C70.5 (3)C17—C12—C13—C140.8 (4)
C6—N4—C7—N30.3 (3)C18—C15—C16—C17179.2 (3)
C6—N4—C7—C8174.2 (2)
4-Phenyl-3-(pyridin-2-yl)-5-(pyrimidin-2-yl)-1,2,4-triazole (L3) top
Crystal data top
C17H12N6Dx = 1.310 Mg m3
Mr = 300.33Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 1290 reflections
a = 8.5626 (16) Åθ = 2.2–16.6°
b = 18.701 (4) ŵ = 0.08 mm1
c = 19.024 (4) ÅT = 293 K
V = 3046.3 (10) Å3Block, clear light colourless
Z = 80.17 × 0.14 × 0.11 mm
F(000) = 1248
Data collection top
Bruker APEXII CCD area detector
diffractometer
1346 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.106
phi and ω scansθmax = 25.1°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 910
Tmin = 0.986, Tmax = 0.991k = 2222
20705 measured reflectionsl = 2222
2701 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.050 w = 1/[σ2(Fo2) + (0.0664P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.135(Δ/σ)max < 0.001
S = 0.92Δρmax = 0.19 e Å3
2701 reflectionsΔρmin = 0.17 e Å3
209 parametersExtinction correction: SHELXL (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
3 restraintsExtinction coefficient: 0.0045 (7)
Primary atom site location: dual
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
xyzUiso*/Ueq
N10.2611 (3)0.63964 (12)0.80798 (11)0.0609 (6)
N20.3929 (3)0.75741 (11)0.67566 (12)0.0654 (7)
N30.3770 (3)0.74752 (12)0.60376 (12)0.0685 (7)
N40.3426 (2)0.64382 (10)0.65638 (10)0.0469 (5)
N50.4212 (3)0.59210 (13)0.50840 (11)0.0711 (7)
N60.2171 (3)0.67474 (12)0.48277 (13)0.0679 (7)
C10.2554 (4)0.63366 (17)0.87791 (15)0.0722 (9)
H10.1834760.6019860.8971800.087*
C20.3495 (4)0.67147 (18)0.92307 (15)0.0815 (9)
H20.3414710.6655120.9714660.098*
C30.4558 (4)0.71830 (17)0.89478 (16)0.0823 (9)
H30.5210220.7447960.9239150.099*
C40.4648 (3)0.72564 (14)0.82340 (15)0.0622 (7)
H40.5358220.7571270.8031270.075*
C50.3672 (3)0.68566 (13)0.78268 (13)0.0511 (7)
C60.3706 (3)0.69515 (13)0.70601 (14)0.0515 (7)
C70.3485 (3)0.67978 (14)0.59342 (14)0.0533 (7)
C80.3275 (3)0.64661 (14)0.52365 (14)0.0547 (7)
C90.2008 (3)0.64351 (18)0.41862 (17)0.0755 (9)
H90.1262240.6613700.3877430.091*
C100.2900 (4)0.58703 (18)0.39810 (16)0.0789 (9)
H100.2771460.5657050.3543170.095*
C110.3995 (4)0.56308 (17)0.44497 (16)0.0830 (10)
H110.4619450.5246060.4319790.100*
C120.3166 (3)0.56847 (13)0.66557 (12)0.0481 (6)
C130.1898 (3)0.53672 (17)0.63395 (15)0.0664 (8)
H130.1185390.5639680.6085850.080*
C140.1701 (4)0.46387 (19)0.64046 (19)0.0875 (10)
H140.0872780.4416380.6176430.105*
C150.2707 (5)0.42387 (17)0.67999 (19)0.0864 (11)
H150.2543800.3749950.6851700.104*
C160.3957 (4)0.45597 (15)0.71197 (15)0.0709 (8)
H160.4643750.4286590.7387020.085*
C170.4207 (3)0.52890 (13)0.70480 (13)0.0538 (7)
H170.5061610.5506920.7260710.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0576 (15)0.0683 (15)0.0567 (15)0.0007 (12)0.0050 (12)0.0074 (12)
N20.0728 (17)0.0475 (14)0.0759 (17)0.0059 (12)0.0065 (13)0.0048 (12)
N30.0804 (18)0.0537 (15)0.0715 (17)0.0008 (13)0.0105 (14)0.0004 (12)
N40.0465 (13)0.0436 (12)0.0506 (13)0.0029 (10)0.0025 (9)0.0021 (10)
N50.0746 (18)0.0815 (18)0.0571 (15)0.0256 (14)0.0045 (13)0.0079 (13)
N60.0593 (16)0.0728 (17)0.0715 (17)0.0032 (12)0.0031 (13)0.0074 (14)
C10.074 (2)0.086 (2)0.0561 (19)0.0075 (17)0.0065 (16)0.0054 (16)
C20.088 (3)0.102 (3)0.0541 (18)0.0295 (17)0.0038 (16)0.0119 (16)
C30.071 (2)0.095 (2)0.0809 (15)0.0189 (15)0.0160 (16)0.0311 (18)
C40.0452 (16)0.0584 (16)0.0831 (15)0.0007 (14)0.0038 (14)0.0199 (15)
C50.0432 (16)0.0506 (16)0.0595 (16)0.0049 (14)0.0008 (13)0.0107 (13)
C60.0464 (16)0.0452 (16)0.0628 (17)0.0034 (13)0.0036 (13)0.0069 (14)
C70.0492 (17)0.0521 (17)0.0587 (17)0.0058 (13)0.0053 (13)0.0045 (14)
C80.0521 (17)0.0583 (17)0.0537 (17)0.0037 (15)0.0046 (14)0.0052 (14)
C90.064 (2)0.090 (2)0.073 (2)0.0006 (18)0.0077 (17)0.0113 (18)
C100.075 (2)0.105 (3)0.0564 (19)0.0201 (19)0.0064 (16)0.0113 (18)
C110.088 (2)0.097 (2)0.063 (2)0.032 (2)0.0099 (19)0.0135 (18)
C120.0486 (16)0.0479 (16)0.0479 (15)0.0063 (13)0.0044 (13)0.0027 (13)
C130.0558 (19)0.071 (2)0.0724 (19)0.0126 (16)0.0048 (15)0.0079 (15)
C140.083 (3)0.072 (2)0.108 (3)0.036 (2)0.002 (2)0.019 (2)
C150.104 (3)0.0479 (19)0.107 (3)0.017 (2)0.023 (2)0.0058 (19)
C160.081 (2)0.0552 (19)0.076 (2)0.0013 (18)0.0086 (18)0.0041 (15)
C170.0573 (18)0.0505 (16)0.0537 (16)0.0038 (13)0.0044 (14)0.0012 (13)
Geometric parameters (Å, º) top
N1—C11.336 (3)C4—C51.363 (3)
N1—C51.341 (3)C5—C61.470 (3)
N2—N31.387 (3)C7—C81.476 (3)
N2—C61.314 (3)C9—H90.9300
N3—C71.305 (3)C9—C101.360 (4)
N4—C61.368 (3)C10—H100.9300
N4—C71.375 (3)C10—C111.369 (4)
N4—C121.437 (3)C11—H110.9300
N5—C81.329 (3)C12—C131.376 (3)
N5—C111.336 (3)C12—C171.378 (3)
N6—C81.332 (3)C13—H130.9300
N6—C91.360 (3)C13—C141.378 (4)
C1—H10.9300C14—H140.9300
C1—C21.374 (4)C14—C151.366 (5)
C2—H20.9300C15—H150.9300
C2—C31.373 (4)C15—C161.370 (4)
C3—H30.9300C16—H160.9300
C3—C41.367 (4)C16—C171.387 (3)
C4—H40.9300C17—H170.9300
C1—N1—C5115.8 (2)N5—C8—C7116.4 (2)
C6—N2—N3107.5 (2)N6—C8—C7116.4 (2)
C7—N3—N2107.3 (2)N6—C9—H9118.9
C6—N4—C7104.6 (2)N6—C9—C10122.2 (3)
C6—N4—C12129.2 (2)C10—C9—H9118.9
C7—N4—C12126.2 (2)C9—C10—H10121.6
C8—N5—C11115.1 (2)C9—C10—C11116.8 (3)
C8—N6—C9115.3 (2)C11—C10—H10121.6
N1—C1—H1118.0N5—C11—C10123.4 (3)
N1—C1—C2123.9 (3)N5—C11—H11118.3
C2—C1—H1118.0C10—C11—H11118.3
C1—C2—H2120.9C13—C12—N4119.5 (2)
C3—C2—C1118.2 (3)C13—C12—C17121.0 (2)
C3—C2—H2120.9C17—C12—N4119.4 (2)
C2—C3—H3120.3C12—C13—H13120.5
C4—C3—C2119.4 (3)C12—C13—C14118.9 (3)
C4—C3—H3120.3C14—C13—H13120.5
C3—C4—H4120.8C13—C14—H14119.5
C5—C4—C3118.3 (3)C15—C14—C13120.9 (3)
C5—C4—H4120.8C15—C14—H14119.5
N1—C5—C4124.3 (3)C14—C15—H15120.1
N1—C5—C6116.5 (2)C14—C15—C16119.8 (3)
C4—C5—C6119.1 (3)C16—C15—H15120.1
N2—C6—N4110.1 (2)C15—C16—H16119.7
N2—C6—C5123.1 (2)C15—C16—C17120.5 (3)
N4—C6—C5126.7 (2)C17—C16—H16119.7
N3—C7—N4110.5 (2)C12—C17—C16118.8 (3)
N3—C7—C8124.5 (2)C12—C17—H17120.6
N4—C7—C8125.0 (2)C16—C17—H17120.6
N5—C8—N6127.1 (3)
N1—C1—C2—C30.0 (5)C6—N4—C7—C8179.0 (2)
N1—C5—C6—N2140.9 (3)C6—N4—C12—C13129.8 (3)
N1—C5—C6—N435.0 (4)C6—N4—C12—C1751.5 (3)
N2—N3—C7—N40.8 (3)C7—N4—C6—N20.4 (3)
N2—N3—C7—C8178.5 (2)C7—N4—C6—C5175.8 (2)
N3—N2—C6—N41.0 (3)C7—N4—C12—C1352.0 (3)
N3—N2—C6—C5175.5 (2)C7—N4—C12—C17126.7 (3)
N3—C7—C8—N5124.0 (3)C8—N5—C11—C100.3 (5)
N3—C7—C8—N655.8 (4)C8—N6—C9—C100.7 (4)
N4—C7—C8—N555.2 (3)C9—N6—C8—N50.1 (4)
N4—C7—C8—N6125.0 (3)C9—N6—C8—C7179.6 (2)
N4—C12—C13—C14177.0 (2)C9—C10—C11—N50.2 (5)
N4—C12—C17—C16178.7 (2)C11—N5—C8—N60.4 (4)
N6—C9—C10—C110.7 (5)C11—N5—C8—C7179.9 (2)
C1—N1—C5—C40.7 (4)C12—N4—C6—N2178.1 (2)
C1—N1—C5—C6177.5 (2)C12—N4—C6—C55.7 (4)
C1—C2—C3—C40.2 (4)C12—N4—C7—N3178.8 (2)
C2—C3—C4—C50.1 (4)C12—N4—C7—C80.5 (4)
C3—C4—C5—N10.6 (4)C12—C13—C14—C152.7 (5)
C3—C4—C5—C6177.4 (2)C13—C12—C17—C160.0 (4)
C4—C5—C6—N236.2 (4)C13—C14—C15—C162.0 (5)
C4—C5—C6—N4148.0 (2)C14—C15—C16—C170.3 (5)
C5—N1—C1—C20.4 (4)C15—C16—C17—C120.7 (4)
C6—N2—N3—C71.1 (3)C17—C12—C13—C141.7 (4)
C6—N4—C7—N30.3 (3)
4-(4-Bromophenyl)-3-(pyridin-2-yl)-5-(pyrimidin-2-yl)-1,2,4-triazole (L4) top
Crystal data top
C17H11BrN6Z = 2
Mr = 379.23F(000) = 380
Triclinic, P1Dx = 1.574 Mg m3
a = 8.5510 (13) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.4214 (15) ÅCell parameters from 2667 reflections
c = 11.5813 (18) Åθ = 2.4–26.1°
α = 85.894 (2)°µ = 2.58 mm1
β = 70.776 (2)°T = 293 K
γ = 65.640 (2)°Block, clear light colourless
V = 800.3 (2) Å30.19 × 0.16 × 0.12 mm
Data collection top
Bruker APEXII CCD area detector
diffractometer
2264 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
phi and ω scansθmax = 25.1°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1010
Tmin = 0.619, Tmax = 0.734k = 1111
5827 measured reflectionsl = 1313
2813 independent reflections
Refinement top
Refinement on F242 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.101 w = 1/[σ2(Fo2) + (0.0343P)2 + 0.7585P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
2813 reflectionsΔρmax = 0.73 e Å3
217 parametersΔρmin = 0.53 e Å3
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
xyzUiso*/Ueq
Br11.27151 (5)0.65581 (6)0.58278 (4)0.07508 (19)
N10.4324 (4)0.9672 (3)0.6896 (3)0.0628 (8)
N20.2244 (3)0.7508 (3)0.8981 (3)0.0520 (7)
N30.2992 (3)0.5913 (3)0.9065 (2)0.0493 (7)
N40.5182 (3)0.6601 (3)0.7952 (2)0.0352 (5)
N50.7600 (4)0.3286 (3)0.7388 (3)0.0595 (8)
N60.5368 (4)0.2789 (4)0.9008 (3)0.0597 (8)
C10.4071 (6)1.1130 (5)0.6604 (4)0.0787 (13)
H10.4799631.1267900.5846410.094*
C20.2789 (6)1.2443 (5)0.7363 (5)0.0808 (13)
H20.2666111.3437480.7127490.097*
C30.1713 (6)1.2240 (5)0.8460 (4)0.0804 (13)
H30.0814771.3103780.8980760.096*
C40.1950 (5)1.0760 (4)0.8804 (3)0.0610 (10)
H40.1232241.0602890.9557990.073*
C50.3291 (4)0.9502 (4)0.7993 (3)0.0461 (8)
C60.3560 (4)0.7900 (4)0.8317 (3)0.0418 (7)
C70.4746 (4)0.5384 (4)0.8451 (3)0.0390 (7)
C80.5994 (4)0.3724 (4)0.8267 (3)0.0400 (7)
C90.6466 (6)0.1271 (5)0.8801 (4)0.0752 (12)
H90.6069120.0573220.9282390.090*
C100.8138 (7)0.0686 (4)0.7920 (4)0.0769 (12)
H100.8879810.0378420.7791150.092*
C110.8660 (6)0.1761 (4)0.7238 (4)0.0768 (12)
H110.9805520.1410220.6642810.092*
C120.6983 (3)0.6579 (3)0.7434 (3)0.0337 (6)
C130.7943 (4)0.6467 (3)0.8207 (3)0.0370 (6)
H130.7445520.6391340.9041500.044*
C140.9656 (4)0.6466 (3)0.7735 (3)0.0421 (7)
H141.0323780.6394050.8245850.050*
C151.0353 (4)0.6575 (4)0.6491 (3)0.0529 (6)
C160.9405 (4)0.6665 (4)0.5715 (3)0.0459 (7)
H160.9912590.6719970.4878540.055*
C170.7694 (4)0.6673 (3)0.6186 (3)0.0407 (7)
H170.7031100.6740010.5672790.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0427 (2)0.1164 (4)0.0665 (3)0.0476 (2)0.00220 (17)0.0005 (2)
N10.0529 (17)0.0464 (17)0.0630 (19)0.0077 (13)0.0040 (15)0.0056 (14)
N20.0300 (13)0.0641 (19)0.0564 (17)0.0192 (13)0.0065 (12)0.0007 (14)
N30.0376 (14)0.0654 (19)0.0476 (15)0.0287 (13)0.0075 (12)0.0036 (13)
N40.0268 (11)0.0404 (13)0.0367 (13)0.0148 (10)0.0072 (10)0.0034 (10)
N50.0580 (17)0.0383 (16)0.0620 (18)0.0166 (13)0.0005 (14)0.0050 (13)
N60.0668 (19)0.0611 (19)0.0567 (18)0.0386 (16)0.0140 (15)0.0175 (14)
C10.071 (3)0.052 (2)0.081 (3)0.009 (2)0.008 (2)0.018 (2)
C20.082 (3)0.045 (2)0.093 (3)0.008 (2)0.027 (3)0.011 (2)
C30.071 (3)0.054 (2)0.084 (3)0.004 (2)0.020 (2)0.013 (2)
C40.0468 (19)0.058 (2)0.056 (2)0.0051 (16)0.0084 (16)0.0042 (17)
C50.0298 (15)0.0451 (18)0.0528 (19)0.0064 (13)0.0116 (14)0.0010 (15)
C60.0269 (14)0.0490 (18)0.0427 (17)0.0117 (13)0.0066 (12)0.0049 (14)
C70.0361 (15)0.0527 (18)0.0346 (15)0.0258 (14)0.0106 (12)0.0062 (13)
C80.0442 (16)0.0481 (18)0.0362 (16)0.0274 (14)0.0135 (13)0.0055 (13)
C90.096 (3)0.066 (3)0.077 (3)0.051 (3)0.025 (3)0.029 (2)
C100.102 (3)0.041 (2)0.080 (3)0.030 (2)0.022 (3)0.0097 (19)
C110.076 (3)0.049 (2)0.073 (3)0.0188 (19)0.007 (2)0.0035 (19)
C120.0274 (12)0.0310 (13)0.0391 (14)0.0129 (10)0.0053 (11)0.0021 (11)
C130.0326 (13)0.0396 (14)0.0348 (14)0.0160 (11)0.0049 (11)0.0032 (11)
C140.0329 (13)0.0486 (16)0.0464 (16)0.0200 (12)0.0107 (12)0.0016 (13)
C150.0381 (9)0.0694 (10)0.0577 (10)0.0385 (8)0.0017 (9)0.0003 (9)
C160.0404 (15)0.0497 (16)0.0393 (15)0.0206 (13)0.0002 (12)0.0021 (13)
C170.0354 (14)0.0467 (16)0.0352 (14)0.0151 (12)0.0080 (11)0.0019 (12)
Geometric parameters (Å, º) top
Br1—C151.903 (3)C4—H40.9300
N1—C11.336 (5)C4—C51.389 (5)
N1—C51.330 (4)C5—C61.471 (5)
N2—N31.380 (4)C7—C81.466 (4)
N2—C61.314 (4)C9—H90.9300
N3—C71.317 (4)C9—C101.363 (6)
N4—C61.374 (4)C10—H100.9300
N4—C71.381 (4)C10—C111.369 (5)
N4—C121.448 (3)C11—H110.9300
N5—C81.329 (4)C12—C131.373 (4)
N5—C111.332 (5)C12—C171.384 (4)
N6—C81.333 (4)C13—H130.9300
N6—C91.333 (5)C13—C141.385 (4)
C1—H10.9300C14—H140.9300
C1—C21.381 (6)C14—C151.381 (4)
C2—H20.9300C15—C161.372 (5)
C2—C31.356 (6)C16—H160.9300
C3—H30.9300C16—C171.380 (4)
C3—C41.373 (6)C17—H170.9300
C5—N1—C1117.1 (3)N5—C8—C7118.4 (3)
C6—N2—N3107.6 (2)N6—C8—C7115.4 (3)
C7—N3—N2107.6 (2)N6—C9—H9118.2
C6—N4—C7104.4 (2)N6—C9—C10123.5 (3)
C6—N4—C12126.8 (2)C10—C9—H9118.2
C7—N4—C12127.1 (2)C9—C10—H10122.0
C8—N5—C11115.9 (3)C9—C10—C11116.0 (4)
C9—N6—C8115.4 (3)C11—C10—H10122.0
N1—C1—H1118.2N5—C11—C10123.0 (4)
N1—C1—C2123.7 (4)N5—C11—H11118.5
C2—C1—H1118.2C10—C11—H11118.5
C1—C2—H2120.9C13—C12—N4118.5 (2)
C3—C2—C1118.1 (4)C13—C12—C17121.6 (3)
C3—C2—H2120.9C17—C12—N4119.9 (3)
C2—C3—H3120.0C12—C13—H13120.2
C2—C3—C4120.0 (4)C12—C13—C14119.6 (3)
C4—C3—H3120.0C14—C13—H13120.2
C3—C4—H4120.9C13—C14—H14120.7
C3—C4—C5118.2 (4)C15—C14—C13118.6 (3)
C5—C4—H4120.9C15—C14—H14120.7
N1—C5—C4122.9 (3)C14—C15—Br1119.1 (3)
N1—C5—C6117.2 (3)C16—C15—Br1119.1 (2)
C4—C5—C6119.8 (3)C16—C15—C14121.8 (3)
N2—C6—N4110.3 (3)C15—C16—H16120.2
N2—C6—C5123.9 (3)C15—C16—C17119.6 (3)
N4—C6—C5125.7 (3)C17—C16—H16120.2
N3—C7—N4110.0 (3)C12—C17—H17120.6
N3—C7—C8123.9 (3)C16—C17—C12118.8 (3)
N4—C7—C8126.0 (2)C16—C17—H17120.6
N5—C8—N6126.2 (3)
Br1—C15—C16—C17179.8 (2)C6—N4—C7—C8176.2 (3)
N1—C1—C2—C30.8 (8)C6—N4—C12—C1394.1 (3)
N1—C5—C6—N2144.9 (3)C6—N4—C12—C1785.8 (4)
N1—C5—C6—N433.1 (5)C7—N4—C6—N20.2 (3)
N2—N3—C7—N40.3 (3)C7—N4—C6—C5178.4 (3)
N2—N3—C7—C8176.3 (3)C7—N4—C12—C1369.0 (4)
N3—N2—C6—N40.0 (3)C7—N4—C12—C17111.1 (3)
N3—N2—C6—C5178.3 (3)C8—N5—C11—C101.4 (7)
N3—C7—C8—N5162.8 (3)C8—N6—C9—C101.6 (6)
N3—C7—C8—N616.2 (4)C9—N6—C8—N52.1 (5)
N4—C7—C8—N512.6 (5)C9—N6—C8—C7176.8 (3)
N4—C7—C8—N6168.4 (3)C9—C10—C11—N51.7 (7)
N4—C12—C13—C14179.1 (2)C11—N5—C8—N60.6 (5)
N4—C12—C17—C16179.4 (3)C11—N5—C8—C7178.2 (3)
N6—C9—C10—C110.1 (7)C12—N4—C6—N2166.3 (3)
C1—N1—C5—C42.4 (6)C12—N4—C6—C515.4 (5)
C1—N1—C5—C6179.7 (3)C12—N4—C7—N3166.3 (3)
C1—C2—C3—C41.8 (7)C12—N4—C7—C817.8 (4)
C2—C3—C4—C50.8 (7)C12—C13—C14—C150.2 (4)
C3—C4—C5—N11.4 (6)C13—C12—C17—C160.5 (4)
C3—C4—C5—C6178.7 (3)C13—C14—C15—Br1179.5 (2)
C4—C5—C6—N232.5 (5)C13—C14—C15—C160.7 (5)
C4—C5—C6—N4149.4 (3)C14—C15—C16—C171.0 (5)
C5—N1—C1—C21.3 (7)C15—C16—C17—C120.4 (4)
C6—N2—N3—C70.2 (3)C17—C12—C13—C140.8 (4)
C6—N4—C7—N30.3 (3)
4-(4-Chlorophenyl)-3-(pyridin-2-yl)-5-(pyrimidin-2-yl)-1,2,4-triazole (L5) top
Crystal data top
C17H11ClN6Z = 2
Mr = 334.77F(000) = 344
Triclinic, P1Dx = 1.407 Mg m3
a = 8.5105 (13) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.3681 (14) ÅCell parameters from 3029 reflections
c = 10.8959 (16) Åθ = 2.6–26.5°
α = 81.355 (2)°µ = 0.25 mm1
β = 82.482 (2)°T = 293 K
γ = 67.388 (2)°Block, clear light colourless
V = 790.3 (2) Å30.18 × 0.17 × 0.14 mm
Data collection top
Bruker APEXII CCD area detector
diffractometer
2383 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.023
phi and ω scansθmax = 25.1°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 910
Tmin = 0.955, Tmax = 0.965k = 1111
5712 measured reflectionsl = 1212
2765 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.102 w = 1/[σ2(Fo2) + (0.0432P)2 + 0.253P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
2765 reflectionsΔρmax = 0.17 e Å3
217 parametersΔρmin = 0.22 e Å3
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
xyzUiso*/Ueq
Cl11.00724 (6)0.66378 (7)0.40056 (5)0.06079 (19)
N10.2531 (2)0.9522 (2)0.30700 (17)0.0638 (5)
N20.17141 (19)0.7360 (2)0.09767 (15)0.0519 (4)
N30.2479 (2)0.5775 (2)0.09445 (15)0.0522 (4)
N40.39452 (17)0.64924 (16)0.20889 (13)0.0376 (3)
N50.5750 (3)0.3255 (2)0.29005 (17)0.0646 (5)
N60.4922 (3)0.2676 (2)0.10816 (17)0.0665 (5)
C10.2042 (4)1.0970 (3)0.3366 (2)0.0814 (8)
H10.2321811.1104080.4125880.098*
C20.1149 (3)1.2277 (3)0.2616 (3)0.0796 (7)
H20.0838161.3262430.2864700.096*
C30.0735 (3)1.2096 (3)0.1510 (2)0.0765 (7)
H30.0123831.2959620.0987100.092*
C40.1226 (3)1.0620 (3)0.1161 (2)0.0616 (6)
H40.0960851.0472370.0400530.074*
C50.2118 (2)0.9370 (2)0.19654 (18)0.0463 (4)
C60.2602 (2)0.7767 (2)0.16599 (16)0.0421 (4)
C70.3809 (2)0.5276 (2)0.16051 (16)0.0416 (4)
C80.4915 (2)0.3633 (2)0.18782 (17)0.0456 (4)
C90.5897 (4)0.1186 (3)0.1370 (3)0.0863 (8)
H90.5935370.0463150.0856120.104*
C100.6844 (4)0.0668 (3)0.2380 (3)0.0933 (9)
H100.7530360.0375100.2549840.112*
C110.6733 (4)0.1761 (3)0.3136 (3)0.0886 (8)
H110.7362490.1447660.3830990.106*
C120.5441 (2)0.64901 (18)0.25914 (15)0.0352 (4)
C130.5468 (2)0.6525 (2)0.38479 (16)0.0423 (4)
H130.4527500.6532740.4392500.051*
C140.6907 (2)0.6547 (2)0.42902 (16)0.0445 (4)
H140.6948640.6571810.5135040.053*
C150.8283 (2)0.6531 (2)0.34571 (16)0.0400 (4)
C160.8273 (2)0.6466 (2)0.22091 (17)0.0443 (4)
H160.9221840.6436820.1666760.053*
C170.6831 (2)0.6444 (2)0.17696 (16)0.0417 (4)
H170.6799230.6397560.0926880.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0501 (3)0.0850 (4)0.0577 (3)0.0339 (3)0.0209 (2)0.0005 (3)
N10.0710 (12)0.0497 (10)0.0616 (11)0.0055 (9)0.0249 (9)0.0084 (8)
N20.0412 (9)0.0643 (11)0.0537 (10)0.0217 (8)0.0122 (7)0.0042 (8)
N30.0477 (9)0.0712 (11)0.0504 (9)0.0333 (8)0.0080 (7)0.0105 (8)
N40.0330 (7)0.0431 (8)0.0391 (8)0.0156 (6)0.0055 (6)0.0058 (6)
N50.0837 (13)0.0436 (10)0.0632 (11)0.0177 (9)0.0148 (10)0.0045 (8)
N60.0839 (13)0.0626 (12)0.0634 (11)0.0359 (10)0.0041 (10)0.0232 (9)
C10.101 (2)0.0564 (14)0.0742 (16)0.0038 (13)0.0302 (14)0.0179 (12)
C20.0843 (18)0.0530 (14)0.0854 (18)0.0039 (12)0.0153 (14)0.0110 (12)
C30.0712 (15)0.0574 (14)0.0769 (17)0.0002 (12)0.0149 (13)0.0074 (12)
C40.0539 (12)0.0676 (14)0.0529 (12)0.0102 (10)0.0164 (10)0.0012 (10)
C50.0352 (9)0.0501 (11)0.0493 (10)0.0111 (8)0.0067 (8)0.0027 (8)
C60.0325 (9)0.0534 (11)0.0397 (9)0.0158 (8)0.0072 (7)0.0001 (8)
C70.0412 (9)0.0513 (10)0.0400 (9)0.0250 (8)0.0001 (7)0.0093 (8)
C80.0509 (11)0.0507 (11)0.0430 (10)0.0284 (9)0.0046 (8)0.0101 (8)
C90.118 (2)0.0662 (17)0.0839 (19)0.0437 (16)0.0127 (17)0.0289 (14)
C100.118 (2)0.0407 (13)0.105 (2)0.0171 (14)0.0076 (19)0.0079 (13)
C110.116 (2)0.0506 (14)0.0872 (19)0.0173 (14)0.0232 (17)0.0028 (13)
C120.0320 (8)0.0336 (8)0.0405 (9)0.0113 (7)0.0085 (7)0.0036 (7)
C130.0377 (9)0.0495 (10)0.0382 (9)0.0156 (8)0.0020 (7)0.0032 (7)
C140.0460 (10)0.0522 (11)0.0355 (9)0.0168 (8)0.0110 (8)0.0025 (8)
C150.0355 (9)0.0394 (9)0.0462 (10)0.0126 (7)0.0157 (7)0.0008 (7)
C160.0355 (9)0.0541 (11)0.0447 (10)0.0182 (8)0.0025 (7)0.0058 (8)
C170.0406 (9)0.0512 (10)0.0357 (9)0.0180 (8)0.0051 (7)0.0080 (7)
Geometric parameters (Å, º) top
Cl1—C151.7495 (16)C4—H40.9300
N1—C11.334 (3)C4—C51.377 (3)
N1—C51.339 (3)C5—C61.475 (3)
N2—N31.377 (2)C7—C81.471 (3)
N2—C61.313 (2)C9—H90.9300
N3—C71.313 (2)C9—C101.367 (4)
N4—C61.368 (2)C10—H100.9300
N4—C71.374 (2)C10—C111.377 (4)
N4—C121.449 (2)C11—H110.9300
N5—C81.329 (3)C12—C131.378 (2)
N5—C111.331 (3)C12—C171.377 (2)
N6—C81.336 (2)C13—H130.9300
N6—C91.335 (3)C13—C141.382 (2)
C1—H10.9300C14—H140.9300
C1—C21.374 (3)C14—C151.381 (3)
C2—H20.9300C15—C161.372 (3)
C2—C31.351 (4)C16—H160.9300
C3—H30.9300C16—C171.383 (2)
C3—C41.379 (3)C17—H170.9300
C1—N1—C5116.48 (18)N5—C8—C7116.99 (16)
C6—N2—N3107.51 (15)N6—C8—C7115.71 (18)
C7—N3—N2107.42 (14)N6—C9—H9118.3
C6—N4—C7104.27 (14)N6—C9—C10123.4 (2)
C6—N4—C12126.84 (14)C10—C9—H9118.3
C7—N4—C12126.36 (14)C9—C10—H10121.6
C8—N5—C11116.1 (2)C9—C10—C11116.9 (2)
C9—N6—C8114.5 (2)C11—C10—H10121.6
N1—C1—H1118.0N5—C11—C10121.9 (3)
N1—C1—C2124.1 (2)N5—C11—H11119.1
C2—C1—H1118.0C10—C11—H11119.1
C1—C2—H2120.8C13—C12—N4120.92 (15)
C3—C2—C1118.5 (2)C17—C12—N4117.61 (14)
C3—C2—H2120.8C17—C12—C13121.47 (15)
C2—C3—H3120.3C12—C13—H13120.4
C2—C3—C4119.5 (2)C12—C13—C14119.27 (16)
C4—C3—H3120.3C14—C13—H13120.4
C3—C4—H4120.7C13—C14—H14120.5
C5—C4—C3118.5 (2)C15—C14—C13118.92 (16)
C5—C4—H4120.7C15—C14—H14120.5
N1—C5—C4123.01 (19)C14—C15—Cl1119.00 (13)
N1—C5—C6116.42 (16)C16—C15—Cl1119.04 (14)
C4—C5—C6120.52 (18)C16—C15—C14121.95 (15)
N2—C6—N4110.45 (16)C15—C16—H16120.5
N2—C6—C5123.32 (16)C15—C16—C17118.96 (16)
N4—C6—C5126.13 (15)C17—C16—H16120.5
N3—C7—N4110.34 (16)C12—C17—C16119.40 (16)
N3—C7—C8124.94 (16)C12—C17—H17120.3
N4—C7—C8124.54 (15)C16—C17—H17120.3
N5—C8—N6127.27 (19)
Cl1—C15—C16—C17177.46 (14)C6—N4—C7—C8175.78 (16)
N1—C1—C2—C30.0 (5)C6—N4—C12—C1390.6 (2)
N1—C5—C6—N2148.07 (19)C6—N4—C12—C1789.8 (2)
N1—C5—C6—N427.9 (3)C7—N4—C6—N20.35 (19)
N2—N3—C7—N40.5 (2)C7—N4—C6—C5176.74 (16)
N2—N3—C7—C8175.73 (15)C7—N4—C12—C13110.35 (19)
N3—N2—C6—N40.1 (2)C7—N4—C12—C1769.3 (2)
N3—N2—C6—C5176.59 (16)C8—N5—C11—C101.5 (4)
N3—C7—C8—N5154.66 (19)C8—N6—C9—C101.1 (4)
N3—C7—C8—N623.3 (3)C9—N6—C8—N50.5 (3)
N4—C7—C8—N519.9 (3)C9—N6—C8—C7178.21 (19)
N4—C7—C8—N6162.08 (17)C9—C10—C11—N50.1 (5)
N4—C12—C13—C14178.95 (16)C11—N5—C8—N61.8 (3)
N4—C12—C17—C16178.94 (15)C11—N5—C8—C7179.5 (2)
N6—C9—C10—C111.3 (5)C12—N4—C6—N2163.09 (15)
C1—N1—C5—C40.5 (3)C12—N4—C6—C520.5 (3)
C1—N1—C5—C6177.8 (2)C12—N4—C7—N3163.36 (16)
C1—C2—C3—C40.5 (4)C12—N4—C7—C821.4 (3)
C2—C3—C4—C50.5 (4)C12—C13—C14—C150.1 (3)
C3—C4—C5—N10.0 (3)C13—C12—C17—C161.4 (3)
C3—C4—C5—C6177.2 (2)C13—C14—C15—Cl1177.46 (13)
C4—C5—C6—N229.4 (3)C13—C14—C15—C161.2 (3)
C4—C5—C6—N4154.69 (18)C14—C15—C16—C171.2 (3)
C5—N1—C1—C20.5 (4)C15—C16—C17—C120.1 (3)
C6—N2—N3—C70.3 (2)C17—C12—C13—C141.4 (3)
C6—N4—C7—N30.51 (19)
4-(4-Fluorophenyl)-3-(pyridin-2-yl)-5-(pyrimidin-2-yl)-1,2,4-triazole (L6) top
Crystal data top
C17H11FN6Z = 2
Mr = 318.32F(000) = 328
Triclinic, P1Dx = 1.386 Mg m3
a = 8.624 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.503 (2) ÅCell parameters from 1265 reflections
c = 10.471 (3) Åθ = 2.4–22.0°
α = 80.312 (3)°µ = 0.10 mm1
β = 81.512 (4)°T = 293 K
γ = 64.780 (3)°Block, clear light colourless
V = 762.5 (3) Å30.18 × 0.14 × 0.12 mm
Data collection top
Bruker APEXII CCD area detector
diffractometer
1778 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
phi and ω scansθmax = 25.1°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1010
Tmin = 0.984, Tmax = 0.988k = 1111
5556 measured reflectionsl = 1212
2676 independent reflections
Refinement top
Refinement on F213 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.138 w = 1/[σ2(Fo2) + (0.0684P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
2676 reflectionsΔρmax = 0.19 e Å3
217 parametersΔρmin = 0.23 e Å3
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
xyzUiso*/Ueq
F10.97294 (17)0.63947 (18)0.39616 (14)0.0802 (5)
N10.2472 (3)0.9553 (2)0.3243 (2)0.0768 (7)
N20.1623 (2)0.7479 (2)0.11258 (19)0.0584 (5)
N30.2434 (2)0.5876 (2)0.10485 (18)0.0557 (5)
N40.39664 (19)0.65217 (19)0.21641 (15)0.0406 (4)
N50.5977 (3)0.3235 (2)0.28799 (18)0.0611 (6)
N60.4896 (3)0.2738 (2)0.1124 (2)0.0671 (6)
C10.1997 (4)1.1000 (3)0.3536 (3)0.0963 (11)
H10.2262241.1110400.4332380.116*
C20.1144 (4)1.2333 (3)0.2740 (3)0.0868 (9)
H20.0861001.3316970.2982270.104*
C30.0725 (4)1.2181 (3)0.1592 (3)0.0786 (9)
H30.0119341.3064410.1039140.094*
C40.1202 (3)1.0709 (3)0.1249 (2)0.0642 (7)
H40.0940691.0582420.0456850.077*
C50.2070 (3)0.9428 (3)0.2098 (2)0.0511 (6)
C60.2547 (3)0.7834 (3)0.1791 (2)0.0473 (6)
C70.3832 (3)0.5337 (2)0.16723 (19)0.0425 (5)
C80.4998 (3)0.3667 (3)0.1904 (2)0.0452 (5)
C90.5904 (4)0.1226 (4)0.1394 (3)0.0834 (9)
H90.5872650.0523640.0889080.100*
C100.6978 (4)0.0647 (3)0.2366 (3)0.0834 (9)
H100.7673610.0415830.2525920.100*
C110.6978 (4)0.1712 (3)0.3093 (3)0.0785 (8)
H110.7703980.1361360.3761340.094*
C120.5457 (2)0.6483 (2)0.26658 (19)0.0398 (5)
C130.5525 (3)0.6463 (2)0.3963 (2)0.0481 (6)
H130.4593900.6483400.4546780.058*
C140.6985 (3)0.6414 (3)0.4407 (2)0.0543 (6)
H140.7057480.6383700.5289560.065*
C150.8314 (3)0.6410 (3)0.3519 (2)0.0516 (6)
C160.8291 (3)0.6428 (3)0.2218 (2)0.0517 (6)
H160.9230120.6416680.1646670.062*
C170.6847 (3)0.6465 (2)0.1761 (2)0.0468 (5)
H170.6795180.6476860.0877900.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0649 (10)0.1008 (12)0.0907 (11)0.0423 (9)0.0384 (8)0.0028 (9)
N10.0919 (17)0.0484 (13)0.0765 (15)0.0051 (11)0.0370 (13)0.0119 (11)
N20.0472 (11)0.0606 (13)0.0704 (13)0.0209 (10)0.0193 (10)0.0063 (10)
N30.0498 (12)0.0662 (14)0.0604 (12)0.0296 (10)0.0129 (9)0.0090 (10)
N40.0365 (10)0.0415 (10)0.0446 (10)0.0143 (8)0.0090 (8)0.0075 (8)
N50.0760 (14)0.0442 (12)0.0597 (12)0.0170 (11)0.0186 (11)0.0074 (9)
N60.0852 (16)0.0583 (14)0.0668 (14)0.0333 (13)0.0060 (11)0.0210 (11)
C10.124 (3)0.0550 (18)0.090 (2)0.0032 (17)0.0455 (19)0.0194 (16)
C20.099 (2)0.0508 (17)0.094 (2)0.0072 (15)0.0263 (18)0.0134 (16)
C30.077 (2)0.0538 (17)0.0804 (19)0.0037 (15)0.0175 (16)0.0021 (14)
C40.0564 (15)0.0623 (17)0.0613 (15)0.0110 (13)0.0156 (12)0.0024 (13)
C50.0399 (12)0.0487 (14)0.0577 (14)0.0099 (10)0.0091 (10)0.0066 (11)
C60.0372 (12)0.0534 (14)0.0502 (13)0.0164 (11)0.0103 (10)0.0038 (11)
C70.0419 (12)0.0511 (13)0.0406 (12)0.0241 (10)0.0022 (9)0.0089 (10)
C80.0481 (13)0.0528 (14)0.0431 (12)0.0288 (11)0.0037 (10)0.0126 (10)
C90.112 (2)0.065 (2)0.084 (2)0.0427 (18)0.0028 (18)0.0306 (16)
C100.107 (2)0.0426 (15)0.089 (2)0.0205 (15)0.0019 (18)0.0112 (15)
C110.094 (2)0.0514 (17)0.0813 (19)0.0182 (15)0.0244 (16)0.0023 (14)
C120.0365 (11)0.0365 (11)0.0478 (12)0.0131 (9)0.0136 (9)0.0053 (9)
C130.0475 (13)0.0528 (14)0.0445 (13)0.0203 (11)0.0068 (10)0.0054 (10)
C140.0628 (16)0.0577 (15)0.0466 (13)0.0251 (12)0.0206 (12)0.0024 (11)
C150.0455 (13)0.0473 (13)0.0678 (16)0.0195 (11)0.0264 (12)0.0025 (11)
C160.0398 (12)0.0593 (15)0.0590 (14)0.0222 (11)0.0065 (10)0.0081 (11)
C170.0440 (12)0.0508 (13)0.0479 (13)0.0193 (11)0.0097 (10)0.0076 (10)
Geometric parameters (Å, º) top
F1—C151.362 (2)C4—H40.9300
N1—C11.334 (3)C4—C51.374 (3)
N1—C51.333 (3)C5—C61.470 (3)
N2—N31.390 (3)C7—C81.474 (3)
N2—C61.306 (3)C9—H90.9300
N3—C71.317 (2)C9—C101.360 (4)
N4—C61.372 (2)C10—H100.9300
N4—C71.368 (2)C10—C111.365 (4)
N4—C121.443 (2)C11—H110.9300
N5—C81.320 (3)C12—C131.365 (3)
N5—C111.332 (3)C12—C171.410 (3)
N6—C81.335 (3)C13—H130.9300
N6—C91.331 (4)C13—C141.385 (3)
C1—H10.9300C14—H140.9300
C1—C21.368 (4)C14—C151.365 (3)
C2—H20.9300C15—C161.362 (3)
C2—C31.352 (4)C16—H160.9300
C3—H30.9300C16—C171.384 (3)
C3—C41.375 (4)C17—H170.9300
C5—N1—C1116.7 (2)N5—C8—C7117.32 (18)
C6—N2—N3107.64 (17)N6—C8—C7115.7 (2)
C7—N3—N2106.77 (17)N6—C9—H9118.1
C6—N4—C12126.52 (17)N6—C9—C10123.9 (3)
C7—N4—C6104.51 (16)C10—C9—H9118.1
C7—N4—C12127.31 (17)C9—C10—H10121.8
C8—N5—C11116.1 (2)C9—C10—C11116.4 (3)
C9—N6—C8114.4 (2)C11—C10—H10121.8
N1—C1—H1117.9N5—C11—C10122.3 (3)
N1—C1—C2124.2 (3)N5—C11—H11118.8
C2—C1—H1117.9C10—C11—H11118.8
C1—C2—H2120.9C13—C12—N4121.55 (18)
C3—C2—C1118.2 (3)C13—C12—C17121.15 (18)
C3—C2—H2120.9C17—C12—N4117.29 (17)
C2—C3—H3120.3C12—C13—H13120.1
C2—C3—C4119.4 (3)C12—C13—C14119.8 (2)
C4—C3—H3120.3C14—C13—H13120.1
C3—C4—H4120.6C13—C14—H14120.8
C5—C4—C3118.8 (2)C15—C14—C13118.4 (2)
C5—C4—H4120.6C15—C14—H14120.8
N1—C5—C4122.7 (2)F1—C15—C14118.0 (2)
N1—C5—C6116.71 (19)F1—C15—C16118.6 (2)
C4—C5—C6120.6 (2)C16—C15—C14123.40 (19)
N2—C6—N4110.47 (19)C15—C16—H16120.6
N2—C6—C5123.29 (19)C15—C16—C17118.9 (2)
N4—C6—C5126.23 (18)C17—C16—H16120.6
N3—C7—N4110.62 (19)C12—C17—H17120.8
N3—C7—C8124.28 (19)C16—C17—C12118.39 (19)
N4—C7—C8124.89 (18)C16—C17—H17120.8
N5—C8—N6126.9 (2)
F1—C15—C16—C17179.15 (19)C6—N4—C7—C8175.15 (19)
N1—C1—C2—C31.3 (5)C6—N4—C12—C1388.4 (3)
N1—C5—C6—N2145.4 (2)C6—N4—C12—C1791.7 (3)
N1—C5—C6—N433.3 (3)C7—N4—C6—N20.0 (2)
N2—N3—C7—N40.4 (2)C7—N4—C6—C5178.8 (2)
N2—N3—C7—C8175.31 (18)C7—N4—C12—C13108.6 (2)
N3—N2—C6—N40.2 (2)C7—N4—C12—C1771.3 (3)
N3—N2—C6—C5178.7 (2)C8—N5—C11—C101.2 (4)
N3—C7—C8—N5157.6 (2)C8—N6—C9—C100.9 (4)
N3—C7—C8—N619.9 (3)C9—N6—C8—N50.2 (4)
N4—C7—C8—N516.7 (3)C9—N6—C8—C7177.0 (2)
N4—C7—C8—N6165.86 (19)C9—C10—C11—N50.6 (4)
N4—C12—C13—C14179.48 (19)C11—N5—C8—N60.8 (4)
N4—C12—C17—C16179.98 (18)C11—N5—C8—C7178.0 (2)
N6—C9—C10—C110.5 (5)C12—N4—C6—N2166.09 (19)
C1—N1—C5—C40.4 (4)C12—N4—C6—C515.1 (3)
C1—N1—C5—C6178.2 (2)C12—N4—C7—N3166.18 (18)
C1—C2—C3—C41.7 (5)C12—N4—C7—C818.9 (3)
C2—C3—C4—C51.1 (4)C12—C13—C14—C151.0 (3)
C3—C4—C5—N10.0 (4)C13—C12—C17—C160.1 (3)
C3—C4—C5—C6177.7 (2)C13—C14—C15—F1178.62 (19)
C4—C5—C6—N232.5 (3)C13—C14—C15—C161.0 (4)
C4—C5—C6—N4148.8 (2)C14—C15—C16—C170.5 (4)
C5—N1—C1—C20.2 (5)C15—C16—C17—C120.1 (3)
C6—N2—N3—C70.4 (2)C17—C12—C13—C140.4 (3)
C6—N4—C7—N30.2 (2)
4-(4-Methylphenyl)-3-(pyridin-2-yl)-5-(pyrimidin-2-yl)-1,2,4-triazole (L2_auto) top
Crystal data top
C18H14N6Dx = 1.279 Mg m3
Mr = 314.35Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 3494 reflections
a = 15.7069 (10) Åθ = 2.5–29.1°
b = 11.8266 (11) ŵ = 0.08 mm1
c = 17.5763 (12) ÅT = 293 K
V = 3265.0 (4) Å3Block, colourless
Z = 80.17 × 0.16 × 0.15 mm
F(000) = 1312
Data collection top
Rigaku XtaLAB Synergy-R DW
diffractometer with a HyPix detector
1901 reflections with I > 2σ(I)
ω scansRint = 0.116
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
θmax = 25.1°, θmin = 2.3°
Tmin = 0.986, Tmax = 0.988h = 1817
13041 measured reflectionsk = 1412
2885 independent reflectionsl = 1920
Refinement top
Refinement on F284 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054H-atom parameters constrained
wR(F2) = 0.157 w = 1/[σ2(Fo2) + (0.0911P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max < 0.001
2885 reflectionsΔρmax = 0.17 e Å3
264 parametersΔρmin = 0.24 e Å3
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
xyzUiso*/UeqOcc. (<1)
N10.7327 (6)0.7143 (9)0.7364 (6)0.072 (2)0.463 (15)
N1A0.7685 (8)0.5238 (10)0.6743 (9)0.077 (3)0.537 (15)
N20.57795 (11)0.6717 (2)0.66033 (10)0.0738 (6)
N30.52512 (11)0.67512 (19)0.59781 (10)0.0689 (6)
N40.65335 (8)0.63004 (14)0.55907 (9)0.0446 (4)
N50.59188 (11)0.69239 (18)0.40577 (10)0.0651 (5)
N60.45851 (10)0.62154 (16)0.44943 (11)0.0613 (5)
C10.7947 (7)0.7092 (12)0.7837 (6)0.092 (3)0.463 (15)
H10.7997690.7659670.8199730.110*0.463 (15)
C1A0.8367 (6)0.4992 (8)0.7145 (6)0.078 (2)0.537 (15)
H1A0.8654110.4319570.7048750.094*0.537 (15)
C20.8541 (6)0.6240 (15)0.7834 (5)0.086 (3)0.463 (15)
H20.8973910.6229520.8194590.103*0.463 (15)
C2A0.8672 (5)0.5713 (8)0.7713 (5)0.069 (2)0.537 (15)
H2A0.9148950.5520540.7998610.083*0.537 (15)
C30.8491 (6)0.5408 (14)0.7296 (7)0.090 (3)0.463 (15)
H30.8896820.4835500.7279830.108*0.463 (15)
C3A0.8251 (6)0.6708 (7)0.7839 (4)0.0682 (19)0.537 (15)
H3A0.8425420.7205970.8218150.082*0.537 (15)
C40.7824 (10)0.5426 (15)0.6771 (11)0.076 (3)0.463 (15)
H40.7763770.4882760.6391980.091*0.463 (15)
C4A0.7561 (7)0.6946 (10)0.7387 (7)0.0680 (18)0.537 (15)
H4A0.7274090.7624020.7465120.082*0.537 (15)
C50.72861 (13)0.6272 (2)0.68533 (12)0.0612 (6)
C60.65382 (12)0.64461 (19)0.63607 (11)0.0556 (6)
C70.57106 (11)0.65062 (17)0.53805 (11)0.0486 (5)
C80.53903 (11)0.65312 (17)0.45930 (11)0.0461 (5)
C90.43020 (15)0.6304 (2)0.37810 (16)0.0722 (7)
H90.3743510.6089880.3680300.087*
C100.47852 (18)0.6690 (2)0.31916 (14)0.0767 (8)
H100.4567600.6738760.2700550.092*
C110.56022 (17)0.7002 (2)0.33530 (13)0.0740 (7)
H110.5946840.7275010.2963990.089*
C120.72520 (10)0.59963 (16)0.51216 (11)0.0429 (5)
C130.72638 (11)0.49870 (19)0.47468 (13)0.0547 (5)
H130.6798120.4502590.4771230.066*
C140.79750 (13)0.4693 (2)0.43310 (14)0.0672 (7)
H140.7984420.4004890.4075590.081*
C150.86783 (12)0.5404 (2)0.42854 (13)0.0604 (6)
C160.86363 (12)0.6421 (2)0.46576 (14)0.0623 (6)
H160.9093710.6918480.4626640.075*
C170.79330 (12)0.67211 (19)0.50752 (12)0.0539 (5)
H170.7917780.7413240.5325890.065*
C180.94599 (16)0.5079 (3)0.38356 (19)0.0980 (10)
H18A0.9816400.5730710.3769070.147*
H18B0.9291060.4794570.3346760.147*
H18C0.9769010.4504410.4105040.147*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.061 (4)0.107 (5)0.047 (3)0.001 (3)0.008 (3)0.016 (3)
N1A0.063 (5)0.093 (3)0.074 (4)0.008 (3)0.021 (4)0.004 (3)
N20.0595 (11)0.1190 (18)0.0427 (10)0.0293 (10)0.0036 (9)0.0048 (10)
N30.0510 (10)0.1107 (17)0.0448 (10)0.0258 (9)0.0043 (8)0.0004 (9)
N40.0369 (8)0.0571 (11)0.0398 (9)0.0040 (6)0.0037 (7)0.0016 (7)
N50.0602 (10)0.0851 (15)0.0499 (11)0.0041 (9)0.0047 (9)0.0098 (9)
N60.0437 (9)0.0784 (14)0.0620 (12)0.0004 (8)0.0043 (9)0.0012 (9)
C10.068 (5)0.140 (7)0.067 (4)0.003 (4)0.015 (4)0.005 (5)
C1A0.069 (3)0.088 (4)0.077 (4)0.000 (3)0.027 (3)0.002 (3)
C20.058 (4)0.141 (9)0.058 (4)0.004 (5)0.013 (4)0.018 (6)
C2A0.054 (3)0.091 (4)0.063 (4)0.002 (3)0.013 (3)0.001 (3)
C30.058 (4)0.142 (8)0.070 (5)0.004 (5)0.017 (4)0.019 (6)
C3A0.063 (4)0.091 (4)0.051 (3)0.000 (3)0.011 (3)0.003 (3)
C40.045 (4)0.117 (6)0.065 (6)0.019 (5)0.008 (4)0.021 (5)
C4A0.062 (4)0.096 (4)0.045 (3)0.009 (3)0.008 (3)0.004 (2)
C50.0477 (11)0.0935 (16)0.0425 (11)0.0015 (10)0.0007 (9)0.0019 (10)
C60.0502 (11)0.0748 (15)0.0416 (11)0.0082 (9)0.0007 (9)0.0048 (9)
C70.0368 (9)0.0627 (13)0.0461 (11)0.0095 (8)0.0046 (8)0.0014 (9)
C80.0392 (9)0.0541 (12)0.0450 (11)0.0058 (7)0.0020 (8)0.0023 (8)
C90.0571 (13)0.0838 (18)0.0756 (17)0.0076 (11)0.0186 (13)0.0107 (13)
C100.0930 (19)0.090 (2)0.0466 (13)0.0229 (14)0.0167 (13)0.0050 (12)
C110.0839 (17)0.091 (2)0.0475 (13)0.0027 (13)0.0076 (13)0.0108 (12)
C120.0341 (8)0.0530 (12)0.0416 (10)0.0002 (7)0.0034 (8)0.0010 (8)
C130.0405 (10)0.0586 (13)0.0648 (13)0.0064 (8)0.0083 (10)0.0091 (10)
C140.0545 (11)0.0686 (16)0.0786 (17)0.0034 (10)0.0156 (12)0.0217 (12)
C150.0438 (10)0.0756 (17)0.0618 (14)0.0020 (9)0.0145 (10)0.0028 (11)
C160.0418 (10)0.0722 (16)0.0730 (16)0.0125 (9)0.0089 (10)0.0013 (12)
C170.0465 (10)0.0546 (13)0.0605 (14)0.0068 (8)0.0048 (10)0.0068 (10)
C180.0659 (15)0.120 (3)0.108 (2)0.0026 (15)0.0404 (16)0.0081 (18)
Geometric parameters (Å, º) top
N1—C11.283 (10)C4—H40.9300
N1—C51.368 (10)C4—C51.317 (14)
N1A—C1A1.316 (11)C4A—H4A0.9300
N1A—C51.387 (11)C4A—C51.304 (11)
N2—N31.377 (2)C5—C61.474 (3)
N2—C61.306 (2)C7—C81.473 (3)
N3—C71.307 (2)C9—H90.9300
N4—C61.364 (2)C9—C101.363 (4)
N4—C71.366 (2)C10—H100.9300
N4—C121.443 (2)C10—C111.365 (4)
N5—C81.338 (2)C11—H110.9300
N5—C111.338 (3)C12—C131.364 (3)
N6—C81.330 (2)C12—C171.373 (3)
N6—C91.334 (3)C13—H130.9300
C1—H10.9300C13—C141.379 (3)
C1—C21.373 (11)C14—H140.9300
C1A—H1A0.9300C14—C151.390 (3)
C1A—C2A1.397 (9)C15—C161.371 (3)
C2—H20.9300C15—C181.510 (3)
C2—C31.367 (11)C16—H160.9300
C2A—H2A0.9300C16—C171.373 (3)
C2A—C3A1.369 (9)C17—H170.9300
C3—H30.9300C18—H18A0.9600
C3—C41.397 (13)C18—H18B0.9600
C3A—H3A0.9300C18—H18C0.9600
C3A—C4A1.373 (10)
C1—N1—C5115.1 (7)N4—C6—C5124.72 (17)
C1A—N1A—C5119.2 (9)N3—C7—N4110.15 (17)
C6—N2—N3107.25 (17)N3—C7—C8124.22 (16)
C7—N3—N2107.59 (16)N4—C7—C8125.51 (16)
C6—N4—C7104.54 (15)N5—C8—C7117.12 (16)
C6—N4—C12126.43 (14)N6—C8—N5126.56 (18)
C7—N4—C12129.03 (16)N6—C8—C7116.21 (17)
C11—N5—C8116.38 (19)N6—C9—H9118.1
C8—N6—C9114.7 (2)N6—C9—C10123.7 (2)
N1—C1—H1118.3C10—C9—H9118.1
N1—C1—C2123.3 (9)C9—C10—H10121.4
C2—C1—H1118.3C9—C10—C11117.1 (2)
N1A—C1A—H1A119.1C11—C10—H10121.4
N1A—C1A—C2A121.9 (9)N5—C11—C10121.6 (2)
C2A—C1A—H1A119.1N5—C11—H11119.2
C1—C2—H2120.3C10—C11—H11119.2
C3—C2—C1119.5 (8)C13—C12—N4120.32 (15)
C3—C2—H2120.3C13—C12—C17120.47 (17)
C1A—C2A—H2A120.8C17—C12—N4119.18 (17)
C3A—C2A—C1A118.4 (8)C12—C13—H13120.4
C3A—C2A—H2A120.8C12—C13—C14119.16 (18)
C2—C3—H3120.4C14—C13—H13120.4
C2—C3—C4119.3 (10)C13—C14—H14119.3
C4—C3—H3120.4C13—C14—C15121.5 (2)
C2A—C3A—H3A121.2C15—C14—H14119.3
C2A—C3A—C4A117.6 (8)C14—C15—C18121.5 (2)
C4A—C3A—H3A121.2C16—C15—C14117.70 (19)
C3—C4—H4122.6C16—C15—C18120.8 (2)
C5—C4—C3114.8 (12)C15—C16—H16119.3
C5—C4—H4122.6C15—C16—C17121.36 (19)
C3A—C4A—H4A118.2C17—C16—H16119.3
C5—C4A—C3A123.5 (8)C12—C17—H17120.1
C5—C4A—H4A118.2C16—C17—C12119.8 (2)
N1—C5—C6108.5 (4)C16—C17—H17120.1
N1A—C5—C6113.6 (5)C15—C18—H18A109.5
C4—C5—N1127.9 (7)C15—C18—H18B109.5
C4—C5—C6123.5 (7)C15—C18—H18C109.5
C4A—C5—N1A119.3 (6)H18A—C18—H18B109.5
C4A—C5—C6126.9 (4)H18A—C18—H18C109.5
N2—C6—N4110.48 (17)H18B—C18—H18C109.5
N2—C6—C5124.75 (19)
N1—C1—C2—C31.3 (15)C4A—C5—C6—N4133.2 (7)
N1—C5—C6—N246.4 (7)C5—N1—C1—C20.9 (14)
N1—C5—C6—N4136.5 (6)C5—N1A—C1A—C2A4.0 (18)
N1A—C1A—C2A—C3A1.1 (14)C6—N2—N3—C70.4 (3)
N1A—C5—C6—N2126.3 (8)C6—N4—C7—N30.3 (2)
N1A—C5—C6—N450.9 (8)C6—N4—C7—C8175.63 (19)
N2—N3—C7—N40.4 (3)C6—N4—C12—C13114.7 (2)
N2—N3—C7—C8175.6 (2)C6—N4—C12—C1763.5 (3)
N3—N2—C6—N40.2 (3)C7—N4—C6—N20.1 (2)
N3—N2—C6—C5177.3 (2)C7—N4—C6—C5177.6 (2)
N3—C7—C8—N5141.3 (2)C7—N4—C12—C1365.3 (3)
N3—C7—C8—N635.2 (3)C7—N4—C12—C17116.5 (2)
N4—C7—C8—N534.1 (3)C8—N5—C11—C100.4 (4)
N4—C7—C8—N6149.4 (2)C8—N6—C9—C100.3 (3)
N4—C12—C13—C14176.98 (19)C9—N6—C8—N50.5 (3)
N4—C12—C17—C16177.20 (19)C9—N6—C8—C7176.68 (18)
N6—C9—C10—C110.2 (4)C9—C10—C11—N50.5 (4)
C1—N1—C5—C43.3 (19)C11—N5—C8—N60.2 (3)
C1—N1—C5—C6179.3 (8)C11—N5—C8—C7176.3 (2)
C1—C2—C3—C41.5 (17)C12—N4—C6—N2179.9 (2)
C1A—N1A—C5—C4A4.5 (18)C12—N4—C6—C52.4 (3)
C1A—N1A—C5—C6179.2 (10)C12—N4—C7—N3179.67 (19)
C1A—C2A—C3A—C4A1.2 (13)C12—N4—C7—C84.4 (3)
C2—C3—C4—C50 (2)C12—C13—C14—C150.1 (4)
C2A—C3A—C4A—C50.6 (16)C13—C12—C17—C161.0 (3)
C3—C4—C5—N13 (2)C13—C14—C15—C161.2 (4)
C3—C4—C5—C6179.9 (9)C13—C14—C15—C18179.5 (2)
C3A—C4A—C5—N1A2.2 (16)C14—C15—C16—C171.4 (4)
C3A—C4A—C5—C6177.9 (7)C15—C16—C17—C120.3 (4)
C4—C5—C6—N2136.0 (12)C17—C12—C13—C141.2 (3)
C4—C5—C6—N441.1 (12)C18—C15—C16—C17179.3 (2)
C4A—C5—C6—N249.6 (8)
Selected bond lengths (Å) and angles (°) for L2·C2H5OH and L2–6 top
L2·C2H5OHL2L3L4L5L6
N1—C11.329 (4)1.283 (10)1.336 (3)1.336 (5)1.334 (3)1.334 (3)
N2—N31.380 (3)1.377 (2)1.387 (3)1.380 (4)1.377 (2)1.390 (3)
N4—C61.368 (3)1.364 (2)1.367 (2)1.374 (3)1.368 (2)1.372 (2)
N5—C81.334 (4)1.338 (2)1.329 (3)1.329 (4)1.329 (3)1.321 (3)
N6—C81.330 (3)1.330 (2)1.332 (3)1.333 (4)1.337 (2)1.335 (3)
C18—C151.515 (4)1.510 (3)
O1—C201.391 (6)
Br1—C151.902 (3)
Cl1—C151.749 (6)
F1—C151.361 (2)
C1—N1—C5116.4 (3)115.1 (7)115.8 (2)117.1 (3)116.5 (2)116.7 (2)
C6—N2—N3107.1 (2)107.25 (17)107.5 (2)107.7 (2)107.5 (2)107.6 (2)
C7—N3—N2107.6 (2)107.58 (16)107.2 (2)107.6 (2)107.3 (2)106.8 (2)
C7—N4—C6104.3 (2)104.54 (15)104.6 (2)104.5 (2)104.2 (3)104.5 (2)
C8—N5—C11115.0 (3)116.38 (19)115.1 (2)115.9 (3)116.0 (2)116.1 (2)
C8—N6—C9114.7 (3)114.7 (2)115.3 (2)115.4 (3)114.5 (2)114.4 (2)
C18—C15—C14121.4 (3)111.3 (7)
O1—C20—C19120.2 (4)
Br1—C15—C14119.1 (2)
Cl1—C15—C14119.0 (2)
F1—C15—C14118.0 (2)
Dihedral angles (°) for L2·C2H5OH and L2–6 top
CompoundPy/TrzPh/TrzPym/Trz
L2·C2H5OH34.4 (2)87.2 (4)34.7 (3)
L250.1 (3)64.4 (5)35.4 (4)
L336.4 (1)51.3 (3)55.6 (1)
L432.7 (7)78.0 (1)15.0 (5)
L529.2 (2)80.4 (6)21.8 (6)
L633.1 (3)80.4 (2)19.0 (1)
Hydrogen-bonding geometry (Å, °) for L2·C2H5OH and L2–6 top
CompoundD—H···AD—HH···AD···AD—H···A
L2·C2H5OHO1—H1A···N30.822.0772.894 (1)174
C11—H11···O1i0.932.6653.328 (3)129
C17—H17···N6ii0.932.7053.570 (2)155
C2—H2···π(Ph)iii0.933.0723.821 (3)139
L2C2A—H2A···N3i0.932.5533.455 (2)164
C11—H11···N1Aii0.932.5053.372 (4)155
C13—H13···N6iii0.932.6663.498 (3)149
L3C9—H9···N3i0.932.7363.467 (2)136
C11—H11···N5ii0.932.6653.401 (1)138
C15—H15···N2iii0.932.5413.415 (3)157
L4C13—H13···N6i0.932.5743.403 (1)149
C14—H14···N2ii0.932.6433.469 (3)148
C10—H10···π(Ph)iii0.933.1853.911 (1)136
L5C16—H16···N2i0.932.5703.405 (1)150
C17—H17···N6ii0.932.6403.470 (6)149
C10–H10···π(Ph)iii0.933.1463.854 (1)134
L6C13—H13···N5i0.932.7043.380 (1)130
C16—H16···N2ii0.932.6133.412 (4)144
C17—H17···N6iii0.932.5543.399 (2)151
C10—H10···π(Ph)iv0.933.2673.965 (1)133
Symmetry codes for L2·C2H5OH: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z+1; (iii) x+1, y, z. For L2: (i) x+1/2, y, -z+3/2; (ii) x, -y+3/2, z-0.5; (iii) -x+1, -y+1, -z+1. For L3: (i) x-1/2, -y+3/2, -z+1; (ii) -x+1, -y+1, -z+1; (iii) -x+1/2, y-1/2, z. For L4: (i) -x+1, -y+1, -z+2; (ii) x+1, y, z; (iii) x-1, y+1, z. For L5: (i) x+1, y, z; (ii) -x+1, -y+1, -z; (iii) x, y-1, z. For L6: (i) -x+1, -y+1, -z+1; (ii) x+1, y, z; (iii) -x+1, -y+1, -z; (iv) x, y-1, z.
The p···π interactions (Å) in L4–6 top
CompoundX···π interactionX···cent
L4Br···π(Trz)ii3.562 (4)
L5Cl···π(Trz)i3.422 (6)
L6F···π(Trz)ii3.469 (3)
Symmetry code: (i/ii) x+1, y, z.
Percentage contribution of the different intermolecular interactions to the Hirshfeld surfaces of L2·C2H5OH and L2–6 top
ContactL2·C2H5OHL2L3L4L5L6
H···H54.547.036.730.432.432.8
N···H/H···N16.128.231.621.822.223.8
C···H/H···C18.120.625.621.920.621.9
O···H/H···O5.1
N···C/C···N1.91.93.44.64.34.4
C···C31.51.92.72.82.8
N···N1.30.80.811.31.1
Br···H/H···Br10.9
Br···N/N···Br3.1
Br···C/C···Br2.5
Br···Br1.2
Cl···H/H···Cl10.8
Cl···N/N···Cl2.4
Cl···C/C···Cl2.7
Cl···Cl0.4
F···H/H···F9.3
F···N/N···F1.6
F···C/C···F1.6
F···F0.6
 

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