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The structural characterization of several polymorphic forms of a compound allow the inter­play between mol­ecular conformation and inter­molecular inter­actions to be studied, which can contribute to the development of strategies for the rational preparation of materials with desirable properties and the tailoring of inter­molecular inter­actions to produce solids with predictable characteristics of inter­est in crystal engineering. The crystal structures of two new polymorphs of 5,6-dimethyl-2-(pyridin-2-yl)-1-[(pyridin-2-yl)meth­yl]-1H-benzimidazole, C20H18N4, are reported. The previously reported polymorph, (1) [Geiger & DeStefano (2014). Acta Cryst. E70, o365], exhibits the space group C2/c, whereas polymorphs (2) and (3) presented here are in the Pnma and P\overline{1} space groups, respectively. The mol­ecular structures of the three forms differ in their orientations of the 2-(pyridin-2-yl)- and 1-[(pyridin-2-yl)meth­yl]- substituents. Density functional theory (DFT) calculations show that the relative energies of the mol­ecule in the three conformations follows the order (1) < (2) < (3), with a spread of 10.6 kJ mol-1. An analysis of the Hirshfeld surfaces shows that the three polymorphs exhibit inter­molecular C-H...N inter­actions, which can be classified into six types. Based on DFT calculations involving pairs of mol­ecules having the observed inter­actions, the C-H...N energy in the systems explored is approximately -11.2 to -14.4 kJ mol-1.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616015837/yp3132sup1.cif
Contains datablocks global, 2, 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616015837/yp31322sup2.hkl
Contains datablock 2

mol

MDL mol file https://doi.org/10.1107/S2053229616015837/yp31322sup4.mol
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616015837/yp31323sup3.hkl
Contains datablock 3

mol

MDL mol file https://doi.org/10.1107/S2053229616015837/yp31323sup5.mol
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229616015837/yp31322sup6.cml
Supplementary material

CCDC references: 1508839; 1486768

Computing details top

For both compounds, data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

(2) 5,6-Dimethyl-2-(pyridin-2-yl)-1-[(pyridin-2-yl)methyl]-1H-benzimidazole top
Crystal data top
C20H18N4Dx = 1.285 Mg m3
Mr = 314.38Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 9958 reflections
a = 7.9688 (5) Åθ = 2.8–25.0°
b = 12.5553 (8) ŵ = 0.08 mm1
c = 32.4903 (18) ÅT = 200 K
V = 3250.7 (3) Å3Block, colourless
Z = 80.60 × 0.50 × 0.40 mm
F(000) = 1328
Data collection top
Bruker SMART X2S benchtop
diffractometer
2872 independent reflections
Radiation source: sealed microfocus tube2542 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromatorRint = 0.068
Detector resolution: 8.3330 pixels mm-1θmax = 25.0°, θmin = 2.5°
ω scansh = 99
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
k = 1414
Tmin = 0.61, Tmax = 0.97l = 3738
58326 measured reflections
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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0585P)2 + 1.8907P]
where P = (Fo2 + 2Fc2)/3
2872 reflections(Δ/σ)max < 0.001
219 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.13331 (19)0.39604 (12)0.11921 (5)0.0273 (4)
N20.24371 (18)0.23267 (12)0.12885 (5)0.0282 (4)
N30.2564 (3)0.37330 (13)0.03304 (6)0.0468 (5)
N40.2229 (2)0.41705 (13)0.10563 (6)0.0383 (4)
C10.1354 (2)0.37890 (14)0.16124 (6)0.0274 (4)
C20.2037 (2)0.27744 (14)0.16682 (6)0.0287 (4)
C30.2216 (2)0.23642 (15)0.20667 (6)0.0314 (4)
H30.26630.16710.21080.038*
C40.1729 (2)0.29855 (16)0.24001 (6)0.0341 (5)
C50.1052 (2)0.40234 (16)0.23375 (6)0.0332 (5)
C60.0850 (2)0.44255 (15)0.19427 (6)0.0319 (4)
H60.03840.51120.18980.038*
C70.1989 (2)0.30526 (14)0.10145 (6)0.0277 (4)
C80.2231 (2)0.28863 (15)0.05676 (6)0.0302 (4)
C90.2147 (3)0.18605 (16)0.04127 (6)0.0406 (5)
H90.1890.12780.05880.049*
C100.2443 (3)0.16985 (18)0.00010 (7)0.0504 (6)
H100.24140.10.01130.06*
C110.2779 (3)0.25515 (18)0.02479 (7)0.0508 (6)
H110.29790.24610.05340.061*
C120.2818 (4)0.35411 (19)0.00715 (7)0.0592 (7)
H120.3040.41330.02450.071*
C130.0601 (2)0.49026 (14)0.09983 (6)0.0296 (4)
H13A0.07490.48510.06960.036*
H13B0.1210.55430.10940.036*
C140.1241 (2)0.50305 (14)0.10935 (5)0.0265 (4)
C150.1855 (3)0.60290 (15)0.12019 (6)0.0332 (4)
H150.11180.66190.12290.04*
C160.3557 (3)0.61455 (17)0.12686 (6)0.0395 (5)
H160.40130.6820.13390.047*
C170.4581 (3)0.52717 (18)0.12310 (7)0.0430 (5)
H170.57560.53290.12750.052*
C180.3865 (3)0.43082 (18)0.11275 (7)0.0471 (6)
H180.45790.37050.11060.057*
C410.1946 (3)0.25577 (19)0.28305 (6)0.0449 (5)
H41A0.23650.18250.28170.067*
H41B0.08630.25680.29730.067*
H41C0.2750.30020.2980.067*
C510.0565 (3)0.46981 (18)0.27030 (6)0.0436 (5)
H51A0.01340.53850.26070.065*
H51B0.15510.48150.28780.065*
H51C0.03060.43320.28620.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0267 (8)0.0257 (8)0.0296 (9)0.0019 (6)0.0004 (6)0.0016 (6)
N20.0281 (8)0.0260 (8)0.0306 (9)0.0002 (6)0.0006 (6)0.0021 (6)
N30.0728 (13)0.0302 (9)0.0374 (10)0.0025 (9)0.0184 (9)0.0024 (8)
N40.0386 (10)0.0277 (8)0.0487 (11)0.0028 (7)0.0060 (8)0.0042 (7)
C10.0230 (9)0.0305 (9)0.0289 (10)0.0025 (7)0.0001 (7)0.0017 (7)
C20.0269 (9)0.0269 (9)0.0324 (10)0.0020 (7)0.0020 (7)0.0016 (7)
C30.0325 (10)0.0279 (9)0.0338 (11)0.0001 (8)0.0022 (8)0.0023 (8)
C40.0311 (10)0.0393 (11)0.0318 (11)0.0049 (8)0.0010 (8)0.0013 (8)
C50.0302 (10)0.0377 (11)0.0317 (11)0.0056 (8)0.0012 (8)0.0031 (8)
C60.0312 (9)0.0300 (10)0.0346 (11)0.0015 (8)0.0004 (8)0.0041 (8)
C70.0239 (9)0.0262 (9)0.0331 (10)0.0015 (7)0.0002 (7)0.0039 (8)
C80.0318 (10)0.0281 (9)0.0307 (10)0.0014 (8)0.0005 (8)0.0015 (8)
C90.0601 (14)0.0298 (10)0.0320 (11)0.0038 (10)0.0036 (10)0.0002 (8)
C100.0824 (18)0.0317 (11)0.0370 (13)0.0064 (11)0.0029 (11)0.0096 (9)
C110.0779 (17)0.0427 (12)0.0320 (12)0.0079 (12)0.0110 (11)0.0040 (10)
C120.100 (2)0.0372 (13)0.0404 (13)0.0020 (13)0.0270 (13)0.0026 (10)
C130.0309 (10)0.0253 (9)0.0327 (10)0.0014 (7)0.0011 (8)0.0012 (7)
C140.0297 (9)0.0268 (9)0.0229 (9)0.0027 (7)0.0030 (7)0.0002 (7)
C150.0376 (10)0.0267 (10)0.0354 (11)0.0043 (8)0.0013 (8)0.0015 (8)
C160.0396 (11)0.0407 (12)0.0383 (12)0.0128 (9)0.0041 (9)0.0017 (9)
C170.0278 (10)0.0560 (14)0.0451 (12)0.0053 (10)0.0039 (9)0.0100 (10)
C180.0332 (11)0.0443 (13)0.0638 (15)0.0090 (9)0.0087 (10)0.0043 (11)
C410.0525 (13)0.0482 (13)0.0339 (12)0.0014 (10)0.0032 (10)0.0062 (10)
C510.0484 (13)0.0468 (12)0.0356 (12)0.0032 (10)0.0024 (9)0.0074 (9)
Geometric parameters (Å, º) top
N1—C71.380 (2)C10—C111.365 (3)
N1—C11.383 (2)C10—H100.95
N1—C131.462 (2)C11—C121.369 (3)
N2—C71.323 (2)C11—H110.95
N2—C21.393 (2)C12—H120.95
N3—C81.339 (3)C13—C141.508 (3)
N3—C121.343 (3)C13—H13A0.99
N4—C181.335 (3)C13—H13B0.99
N4—C141.342 (2)C14—C151.391 (3)
C1—C21.397 (2)C15—C161.382 (3)
C1—C61.397 (3)C15—H150.95
C2—C31.401 (3)C16—C171.373 (3)
C3—C41.390 (3)C16—H160.95
C3—H30.95C17—C181.379 (3)
C4—C51.425 (3)C17—H170.95
C4—C411.508 (3)C18—H180.95
C5—C61.388 (3)C41—H41A0.98
C5—C511.509 (3)C41—H41B0.98
C6—H60.95C41—H41C0.98
C7—C81.480 (3)C51—H51A0.98
C8—C91.384 (3)C51—H51B0.98
C9—C101.380 (3)C51—H51C0.98
C9—H90.95
C7—N1—C1106.25 (15)C12—C11—H11121.0
C7—N1—C13129.76 (16)N3—C12—C11124.5 (2)
C1—N1—C13123.79 (15)N3—C12—H12117.7
C7—N2—C2104.84 (15)C11—C12—H12117.7
C8—N3—C12116.53 (18)N1—C13—C14112.74 (15)
C18—N4—C14116.94 (17)N1—C13—H13A109.0
N1—C1—C2105.94 (15)C14—C13—H13A109.0
N1—C1—C6131.78 (17)N1—C13—H13B109.0
C2—C1—C6122.28 (17)C14—C13—H13B109.0
N2—C2—C1110.03 (16)H13A—C13—H13B107.8
N2—C2—C3130.31 (17)N4—C14—C15122.80 (17)
C1—C2—C3119.66 (17)N4—C14—C13117.83 (16)
C4—C3—C2119.05 (17)C15—C14—C13119.34 (16)
C4—C3—H3120.5C16—C15—C14118.71 (19)
C2—C3—H3120.5C16—C15—H15120.6
C3—C4—C5120.51 (17)C14—C15—H15120.6
C3—C4—C41119.39 (18)C17—C16—C15119.02 (19)
C5—C4—C41120.10 (18)C17—C16—H16120.5
C6—C5—C4120.56 (17)C15—C16—H16120.5
C6—C5—C51119.54 (19)C16—C17—C18118.47 (19)
C4—C5—C51119.89 (18)C16—C17—H17120.8
C5—C6—C1117.94 (18)C18—C17—H17120.8
C5—C6—H6121.0N4—C18—C17124.1 (2)
C1—C6—H6121.0N4—C18—H18118.0
N2—C7—N1112.94 (16)C17—C18—H18118.0
N2—C7—C8121.86 (16)C4—C41—H41A109.5
N1—C7—C8125.18 (16)C4—C41—H41B109.5
N3—C8—C9122.61 (18)H41A—C41—H41B109.5
N3—C8—C7118.58 (16)C4—C41—H41C109.5
C9—C8—C7118.79 (17)H41A—C41—H41C109.5
C10—C9—C8118.9 (2)H41B—C41—H41C109.5
C10—C9—H9120.6C5—C51—H51A109.5
C8—C9—H9120.6C5—C51—H51B109.5
C11—C10—C9119.4 (2)H51A—C51—H51B109.5
C11—C10—H10120.3C5—C51—H51C109.5
C9—C10—H10120.3H51A—C51—H51C109.5
C10—C11—C12118.1 (2)H51B—C51—H51C109.5
C10—C11—H11121.0
C7—N1—C1—C20.21 (19)C1—N1—C7—C8179.01 (16)
C13—N1—C1—C2175.47 (15)C13—N1—C7—C86.1 (3)
C7—N1—C1—C6179.90 (19)C12—N3—C8—C90.0 (3)
C13—N1—C1—C64.8 (3)C12—N3—C8—C7178.3 (2)
C7—N2—C2—C10.57 (19)N2—C7—C8—N3147.33 (19)
C7—N2—C2—C3179.25 (19)N1—C7—C8—N330.9 (3)
N1—C1—C2—N20.2 (2)N2—C7—C8—C931.1 (3)
C6—C1—C2—N2179.51 (16)N1—C7—C8—C9150.64 (19)
N1—C1—C2—C3179.63 (16)N3—C8—C9—C101.1 (3)
C6—C1—C2—C30.6 (3)C7—C8—C9—C10177.28 (19)
N2—C2—C3—C4179.31 (18)C8—C9—C10—C111.3 (4)
C1—C2—C3—C40.9 (3)C9—C10—C11—C120.4 (4)
C2—C3—C4—C50.2 (3)C8—N3—C12—C110.9 (4)
C2—C3—C4—C41178.91 (18)C10—C11—C12—N30.7 (5)
C3—C4—C5—C60.8 (3)C7—N1—C13—C14114.6 (2)
C41—C4—C5—C6179.87 (18)C1—N1—C13—C1459.5 (2)
C3—C4—C5—C51178.65 (18)C18—N4—C14—C150.2 (3)
C41—C4—C5—C510.5 (3)C18—N4—C14—C13177.67 (18)
C4—C5—C6—C11.0 (3)N1—C13—C14—N446.8 (2)
C51—C5—C6—C1178.42 (17)N1—C13—C14—C15135.30 (18)
N1—C1—C6—C5179.34 (18)N4—C14—C15—C160.9 (3)
C2—C1—C6—C50.3 (3)C13—C14—C15—C16176.88 (17)
C2—N2—C7—N10.73 (19)C14—C15—C16—C170.8 (3)
C2—N2—C7—C8179.19 (16)C15—C16—C17—C180.0 (3)
C1—N1—C7—N20.6 (2)C14—N4—C18—C170.7 (3)
C13—N1—C7—N2175.49 (16)C16—C17—C18—N40.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13A···N30.992.343.052 (3)128
C13—H13B···N2i0.992.563.549 (2)173
C11—H11···N4ii0.952.673.402 (3)135
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x+1/2, y+1/2, z.
(3) 5,6-Dimethyl-2-(pyridin-2-yl)-1-[(pyridin-2-yl)methyl]-1H-benzimidazole top
Crystal data top
C20H18N4Z = 2
Mr = 314.38F(000) = 332
Triclinic, P1Dx = 1.256 Mg m3
a = 6.1920 (18) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.214 (3) ÅCell parameters from 3700 reflections
c = 16.488 (5) Åθ = 2.5–25.2°
α = 85.335 (9)°µ = 0.08 mm1
β = 85.257 (9)°T = 200 K
γ = 85.774 (9)°Block, colourless
V = 831.1 (4) Å30.50 × 0.40 × 0.40 mm
Data collection top
Bruker SMART X2S benchtop
diffractometer
2964 independent reflections
Radiation source: sealed microfocus tube2061 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromatorRint = 0.074
Detector resolution: 8.3330 pixels mm-1θmax = 25.4°, θmin = 2.5°
ω scansh = 77
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
k = 99
Tmin = 0.40, Tmax = 0.97l = 1919
9072 measured reflections
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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.196H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.1081P)2 + 0.0053P]
where P = (Fo2 + 2Fc2)/3
2964 reflections(Δ/σ)max < 0.001
219 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.26 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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.7259 (3)0.6674 (2)0.73758 (10)0.0383 (5)
N20.3894 (3)0.7900 (2)0.75758 (11)0.0396 (5)
N30.7628 (4)0.6764 (3)0.91370 (13)0.0646 (7)
N41.0980 (3)0.3080 (2)0.78326 (12)0.0508 (6)
C10.6457 (4)0.6990 (2)0.66084 (13)0.0383 (5)
C20.4390 (3)0.7756 (2)0.67451 (13)0.0373 (5)
C30.3137 (4)0.8233 (2)0.60796 (13)0.0418 (6)
H30.17290.8760.61670.05*
C40.3974 (4)0.7929 (3)0.52988 (14)0.0438 (6)
C50.6089 (4)0.7137 (3)0.51690 (13)0.0449 (6)
C60.7334 (4)0.6674 (3)0.58233 (13)0.0429 (6)
H60.87480.61550.57390.052*
C70.5631 (4)0.7234 (2)0.79296 (13)0.0379 (5)
C80.5730 (4)0.7172 (3)0.88284 (13)0.0421 (6)
C90.3867 (5)0.7563 (4)0.93111 (16)0.0661 (8)
H90.25360.78530.90710.079*
C100.3954 (5)0.7529 (4)1.01471 (17)0.0779 (9)
H100.26870.781.04880.094*
C110.5898 (5)0.7097 (4)1.04777 (17)0.0699 (8)
H110.60060.70441.10510.084*
C120.7664 (5)0.6748 (4)0.99578 (17)0.0776 (9)
H120.90140.64741.01860.093*
C130.9315 (3)0.5740 (2)0.75159 (14)0.0415 (5)
H13A0.98940.61120.80060.05*
H13B1.03710.59840.70450.05*
C140.9141 (3)0.3904 (2)0.76334 (11)0.0341 (5)
C150.7271 (4)0.3144 (3)0.75338 (13)0.0430 (6)
H150.59790.37680.73990.052*
C160.7326 (4)0.1437 (3)0.76353 (15)0.0532 (7)
H160.60680.08810.75680.064*
C170.9217 (5)0.0570 (3)0.78328 (17)0.0594 (7)
H170.93030.05920.78990.071*
C181.0972 (4)0.1431 (3)0.79319 (18)0.0626 (7)
H181.2270.08310.8080.075*
C410.2616 (5)0.8433 (3)0.45814 (15)0.0595 (7)
H41A0.11820.88870.47830.089*
H41B0.24490.74740.42810.089*
H41C0.33430.92630.42180.089*
C510.6995 (5)0.6796 (3)0.43136 (15)0.0615 (7)
H51A0.61060.60220.40940.092*
H51B0.84930.63240.43290.092*
H51C0.69730.7820.39640.092*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0354 (10)0.0353 (9)0.0442 (11)0.0030 (8)0.0070 (8)0.0041 (7)
N20.0354 (10)0.0401 (10)0.0430 (10)0.0030 (8)0.0045 (8)0.0048 (8)
N30.0493 (13)0.0950 (18)0.0486 (13)0.0060 (12)0.0111 (10)0.0023 (11)
N40.0348 (11)0.0445 (11)0.0732 (14)0.0053 (9)0.0110 (10)0.0052 (9)
C10.0395 (12)0.0327 (10)0.0439 (12)0.0024 (9)0.0089 (10)0.0032 (9)
C20.0354 (12)0.0310 (10)0.0455 (12)0.0004 (9)0.0054 (9)0.0027 (8)
C30.0361 (12)0.0419 (12)0.0472 (13)0.0023 (9)0.0086 (10)0.0018 (9)
C40.0455 (13)0.0406 (12)0.0463 (13)0.0035 (10)0.0083 (10)0.0038 (9)
C50.0477 (14)0.0463 (12)0.0421 (13)0.0075 (10)0.0040 (11)0.0069 (10)
C60.0360 (12)0.0420 (12)0.0503 (14)0.0014 (10)0.0003 (10)0.0077 (10)
C70.0406 (12)0.0302 (10)0.0430 (12)0.0015 (9)0.0050 (10)0.0034 (8)
C80.0439 (13)0.0388 (11)0.0438 (13)0.0025 (10)0.0067 (10)0.0022 (9)
C90.0501 (16)0.101 (2)0.0465 (15)0.0059 (15)0.0037 (12)0.0142 (14)
C100.0612 (19)0.127 (3)0.0450 (16)0.0028 (18)0.0001 (14)0.0171 (16)
C110.070 (2)0.097 (2)0.0450 (15)0.0091 (16)0.0113 (14)0.0073 (14)
C120.0594 (19)0.123 (3)0.0515 (17)0.0037 (18)0.0186 (15)0.0059 (16)
C130.0323 (11)0.0405 (12)0.0524 (13)0.0010 (9)0.0087 (10)0.0039 (9)
C140.0333 (11)0.0392 (11)0.0298 (10)0.0026 (9)0.0035 (8)0.0064 (8)
C150.0387 (12)0.0453 (12)0.0464 (13)0.0031 (10)0.0090 (10)0.0062 (9)
C160.0524 (15)0.0480 (13)0.0616 (16)0.0151 (12)0.0054 (12)0.0065 (11)
C170.0661 (18)0.0353 (12)0.0759 (18)0.0008 (12)0.0003 (14)0.0073 (11)
C180.0472 (15)0.0445 (14)0.095 (2)0.0114 (12)0.0123 (14)0.0031 (13)
C410.0582 (16)0.0703 (17)0.0516 (15)0.0034 (14)0.0174 (13)0.0017 (12)
C510.0617 (17)0.0744 (18)0.0489 (15)0.0021 (14)0.0009 (13)0.0160 (13)
Geometric parameters (Å, º) top
N1—C71.382 (3)C10—C111.373 (4)
N1—C11.395 (3)C10—H100.95
N1—C131.462 (3)C11—C121.361 (5)
N2—C71.327 (3)C11—H110.95
N2—C21.391 (3)C12—H120.95
N3—C81.329 (3)C13—C141.515 (3)
N3—C121.354 (3)C13—H13A0.99
N4—C141.332 (3)C13—H13B0.99
N4—C181.351 (3)C14—C151.383 (3)
C1—C21.394 (3)C15—C161.397 (3)
C1—C61.398 (3)C15—H150.95
C2—C31.409 (3)C16—C171.374 (4)
C3—C41.382 (3)C16—H160.95
C3—H30.95C17—C181.367 (4)
C4—C51.427 (3)C17—H170.95
C4—C411.520 (3)C18—H180.95
C5—C61.389 (3)C41—H41A0.98
C5—C511.514 (3)C41—H41B0.98
C6—H60.95C41—H41C0.98
C7—C81.485 (3)C51—H51A0.98
C8—C91.379 (4)C51—H51B0.98
C9—C101.382 (4)C51—H51C0.98
C9—H90.95
C7—N1—C1106.00 (18)C10—C11—H11121.1
C7—N1—C13129.92 (18)N3—C12—C11124.5 (3)
C1—N1—C13123.64 (18)N3—C12—H12117.8
C7—N2—C2104.97 (18)C11—C12—H12117.8
C8—N3—C12116.8 (2)N1—C13—C14114.18 (17)
C14—N4—C18117.16 (19)N1—C13—H13A108.7
C2—C1—N1105.85 (19)C14—C13—H13A108.7
C2—C1—C6121.71 (19)N1—C13—H13B108.7
N1—C1—C6132.4 (2)C14—C13—H13B108.7
N2—C2—C1110.30 (17)H13A—C13—H13B107.6
N2—C2—C3130.0 (2)N4—C14—C15122.83 (19)
C1—C2—C3119.7 (2)N4—C14—C13113.50 (18)
C4—C3—C2119.5 (2)C15—C14—C13123.66 (19)
C4—C3—H3120.3C14—C15—C16118.5 (2)
C2—C3—H3120.3C14—C15—H15120.8
C3—C4—C5120.2 (2)C16—C15—H15120.8
C3—C4—C41119.5 (2)C17—C16—C15119.3 (2)
C5—C4—C41120.3 (2)C17—C16—H16120.3
C6—C5—C4120.5 (2)C15—C16—H16120.3
C6—C5—C51119.5 (2)C18—C17—C16118.0 (2)
C4—C5—C51120.1 (2)C18—C17—H17121.0
C5—C6—C1118.5 (2)C16—C17—H17121.0
C5—C6—H6120.8N4—C18—C17124.2 (2)
C1—C6—H6120.8N4—C18—H18117.9
N2—C7—N1112.87 (19)C17—C18—H18117.9
N2—C7—C8121.1 (2)C4—C41—H41A109.5
N1—C7—C8126.0 (2)C4—C41—H41B109.5
N3—C8—C9122.4 (2)H41A—C41—H41B109.5
N3—C8—C7118.5 (2)C4—C41—H41C109.5
C9—C8—C7119.1 (2)H41A—C41—H41C109.5
C8—C9—C10119.4 (3)H41B—C41—H41C109.5
C8—C9—H9120.3C5—C51—H51A109.5
C10—C9—H9120.3C5—C51—H51B109.5
C11—C10—C9119.0 (3)H51A—C51—H51B109.5
C11—C10—H10120.5C5—C51—H51C109.5
C9—C10—H10120.5H51A—C51—H51C109.5
C12—C11—C10117.8 (3)H51B—C51—H51C109.5
C12—C11—H11121.1
C7—N1—C1—C21.1 (2)C1—N1—C7—C8179.70 (18)
C13—N1—C1—C2174.10 (17)C13—N1—C7—C87.9 (3)
C7—N1—C1—C6178.6 (2)C12—N3—C8—C90.0 (4)
C13—N1—C1—C65.6 (3)C12—N3—C8—C7178.9 (2)
C7—N2—C2—C10.0 (2)N2—C7—C8—N3168.1 (2)
C7—N2—C2—C3179.0 (2)N1—C7—C8—N310.3 (3)
N1—C1—C2—N20.7 (2)N2—C7—C8—C910.8 (3)
C6—C1—C2—N2179.01 (18)N1—C7—C8—C9170.8 (2)
N1—C1—C2—C3179.85 (17)N3—C8—C9—C100.3 (4)
C6—C1—C2—C30.1 (3)C7—C8—C9—C10179.1 (2)
N2—C2—C3—C4178.70 (19)C8—C9—C10—C110.3 (5)
C1—C2—C3—C40.2 (3)C9—C10—C11—C121.1 (5)
C2—C3—C4—C50.0 (3)C8—N3—C12—C110.9 (5)
C2—C3—C4—C41179.58 (19)C10—C11—C12—N31.4 (5)
C3—C4—C5—C60.4 (3)C7—N1—C13—C1485.2 (2)
C41—C4—C5—C6180.0 (2)C1—N1—C13—C1486.0 (2)
C3—C4—C5—C51179.60 (19)C18—N4—C14—C150.5 (3)
C41—C4—C5—C510.1 (3)C18—N4—C14—C13178.7 (2)
C4—C5—C6—C10.5 (3)N1—C13—C14—N4174.33 (17)
C51—C5—C6—C1179.49 (19)N1—C13—C14—C156.5 (3)
C2—C1—C6—C50.3 (3)N4—C14—C15—C160.9 (3)
N1—C1—C6—C5179.4 (2)C13—C14—C15—C16178.1 (2)
C2—N2—C7—N10.7 (2)C14—C15—C16—C170.3 (4)
C2—N2—C7—C8179.33 (17)C15—C16—C17—C180.8 (4)
C1—N1—C7—N21.2 (2)C14—N4—C18—C170.7 (4)
C13—N1—C7—N2173.57 (18)C16—C17—C18—N41.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13A···N30.992.312.953 (3)121
C18—H18···N2i0.952.713.370 (3)127
C11—H11···N4ii0.952.723.508 (3)141
Symmetry codes: (i) x+1, y1, z; (ii) x+2, y+1, z+2.
Selected geometrical parameters (Å, °) top
(1)a(2)(3)
N1—C71.386 (3)1.380 (2)1.382 (3)
N1—C131.462 (2)1.462 (2)1.462 (3)
C7—C81.474 (3)1.480 (3)1.485 (3)
C13—C141.508 (3)1.509 (2)1.515 (2)
N1—C7—C8126.37 (17)125.18 (16)126.0 (2)
N1—C13—C14113.04 (15)112.72 (14)114.16 (15)
N1—C7—C8—N31.5 (3)31.0 (3)10.3 (3)
N1—C13—C14—N4171.72 (18)-46.8 (2)-174.32 (17)
Reference: (a) Geiger & DeStefano (2014).
 

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