Conformational differences and inter­molecular C—H...N inter­actions in three polymorphs of a bis­(pyridin­yl)-substituted benzimidazole

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 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.

Computing details

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

Crystal data

C20H18N4	Dx = 1.285 Mg m^−3
Mr = 314.38	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9958 reflections
a = 7.9688 (5) Å	θ = 2.8–25.0°
b = 12.5553 (8) Å	µ = 0.08 mm^−1
c = 32.4903 (18) Å	T = 200 K
V = 3250.7 (3) Å^3	Block, colourless
Z = 8	0.60 × 0.50 × 0.40 mm
F(000) = 1328

Data collection

Bruker SMART X2S benchtop diffractometer	2872 independent reflections
Radiation source: sealed microfocus tube	2542 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.068
Detector resolution: 8.3330 pixels mm^-1	θmax = 25.0°, θmin = 2.5°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −14→14
Tmin = 0.61, Tmax = 0.97	l = −37→38
58326 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.139	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0585P)^2 + 1.8907P] where P = (Fo^2 + 2Fc^2)/3
2872 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.13331 (19)	0.39604 (12)	0.11921 (5)	0.0273 (4)
N2	0.24371 (18)	0.23267 (12)	0.12885 (5)	0.0282 (4)
N3	0.2564 (3)	0.37330 (13)	0.03304 (6)	0.0468 (5)
N4	−0.2229 (2)	0.41705 (13)	0.10563 (6)	0.0383 (4)
C1	0.1354 (2)	0.37890 (14)	0.16124 (6)	0.0274 (4)
C2	0.2037 (2)	0.27744 (14)	0.16682 (6)	0.0287 (4)
C3	0.2216 (2)	0.23642 (15)	0.20667 (6)	0.0314 (4)
H3	0.2663	0.1671	0.2108	0.038*
C4	0.1729 (2)	0.29855 (16)	0.24001 (6)	0.0341 (5)
C5	0.1052 (2)	0.40234 (16)	0.23375 (6)	0.0332 (5)
C6	0.0850 (2)	0.44255 (15)	0.19427 (6)	0.0319 (4)
H6	0.0384	0.5112	0.1898	0.038*
C7	0.1989 (2)	0.30526 (14)	0.10145 (6)	0.0277 (4)
C8	0.2231 (2)	0.28863 (15)	0.05676 (6)	0.0302 (4)
C9	0.2147 (3)	0.18605 (16)	0.04127 (6)	0.0406 (5)
H9	0.189	0.1278	0.0588	0.049*
C10	0.2443 (3)	0.16985 (18)	−0.00010 (7)	0.0504 (6)
H10	0.2414	0.1	−0.0113	0.06*
C11	0.2779 (3)	0.25515 (18)	−0.02479 (7)	0.0508 (6)
H11	0.2979	0.2461	−0.0534	0.061*
C12	0.2818 (4)	0.35411 (19)	−0.00715 (7)	0.0592 (7)
H12	0.304	0.4133	−0.0245	0.071*
C13	0.0601 (2)	0.49026 (14)	0.09983 (6)	0.0296 (4)
H13A	0.0749	0.4851	0.0696	0.036*
H13B	0.121	0.5543	0.1094	0.036*
C14	−0.1241 (2)	0.50305 (14)	0.10935 (5)	0.0265 (4)
C15	−0.1855 (3)	0.60290 (15)	0.12019 (6)	0.0332 (4)
H15	−0.1118	0.6619	0.1229	0.04*
C16	−0.3557 (3)	0.61455 (17)	0.12686 (6)	0.0395 (5)
H16	−0.4013	0.682	0.1339	0.047*
C17	−0.4581 (3)	0.52717 (18)	0.12310 (7)	0.0430 (5)
H17	−0.5756	0.5329	0.1275	0.052*
C18	−0.3865 (3)	0.43082 (18)	0.11275 (7)	0.0471 (6)
H18	−0.4579	0.3705	0.1106	0.057*
C41	0.1946 (3)	0.25577 (19)	0.28305 (6)	0.0449 (5)
H41A	0.2365	0.1825	0.2817	0.067*
H41B	0.0863	0.2568	0.2973	0.067*
H41C	0.275	0.3002	0.298	0.067*
C51	0.0565 (3)	0.46981 (18)	0.27030 (6)	0.0436 (5)
H51A	0.0134	0.5385	0.2607	0.065*
H51B	0.1551	0.4815	0.2878	0.065*
H51C	−0.0306	0.4332	0.2862	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0267 (8)	0.0257 (8)	0.0296 (9)	0.0019 (6)	0.0004 (6)	−0.0016 (6)
N2	0.0281 (8)	0.0260 (8)	0.0306 (9)	0.0002 (6)	−0.0006 (6)	−0.0021 (6)
N3	0.0728 (13)	0.0302 (9)	0.0374 (10)	−0.0025 (9)	0.0184 (9)	−0.0024 (8)
N4	0.0386 (10)	0.0277 (8)	0.0487 (11)	−0.0028 (7)	−0.0060 (8)	−0.0042 (7)
C1	0.0230 (9)	0.0305 (9)	0.0289 (10)	−0.0025 (7)	−0.0001 (7)	−0.0017 (7)
C2	0.0269 (9)	0.0269 (9)	0.0324 (10)	−0.0020 (7)	−0.0020 (7)	−0.0016 (7)
C3	0.0325 (10)	0.0279 (9)	0.0338 (11)	0.0001 (8)	−0.0022 (8)	0.0023 (8)
C4	0.0311 (10)	0.0393 (11)	0.0318 (11)	−0.0049 (8)	−0.0010 (8)	0.0013 (8)
C5	0.0302 (10)	0.0377 (11)	0.0317 (11)	−0.0056 (8)	0.0012 (8)	−0.0031 (8)
C6	0.0312 (9)	0.0300 (10)	0.0346 (11)	0.0015 (8)	−0.0004 (8)	−0.0041 (8)
C7	0.0239 (9)	0.0262 (9)	0.0331 (10)	−0.0015 (7)	0.0002 (7)	−0.0039 (8)
C8	0.0318 (10)	0.0281 (9)	0.0307 (10)	0.0014 (8)	0.0005 (8)	−0.0015 (8)
C9	0.0601 (14)	0.0298 (10)	0.0320 (11)	0.0038 (10)	−0.0036 (10)	0.0002 (8)
C10	0.0824 (18)	0.0317 (11)	0.0370 (13)	0.0064 (11)	−0.0029 (11)	−0.0096 (9)
C11	0.0779 (17)	0.0427 (12)	0.0320 (12)	0.0079 (12)	0.0110 (11)	−0.0040 (10)
C12	0.100 (2)	0.0372 (13)	0.0404 (13)	0.0020 (13)	0.0270 (13)	0.0026 (10)
C13	0.0309 (10)	0.0253 (9)	0.0327 (10)	0.0014 (7)	0.0011 (8)	0.0012 (7)
C14	0.0297 (9)	0.0268 (9)	0.0229 (9)	0.0027 (7)	−0.0030 (7)	0.0002 (7)
C15	0.0376 (10)	0.0267 (10)	0.0354 (11)	0.0043 (8)	−0.0013 (8)	−0.0015 (8)
C16	0.0396 (11)	0.0407 (12)	0.0383 (12)	0.0128 (9)	−0.0041 (9)	−0.0017 (9)
C17	0.0278 (10)	0.0560 (14)	0.0451 (12)	0.0053 (10)	−0.0039 (9)	0.0100 (10)
C18	0.0332 (11)	0.0443 (13)	0.0638 (15)	−0.0090 (9)	−0.0087 (10)	0.0043 (11)
C41	0.0525 (13)	0.0482 (13)	0.0339 (12)	−0.0014 (10)	−0.0032 (10)	0.0062 (10)
C51	0.0484 (13)	0.0468 (12)	0.0356 (12)	−0.0032 (10)	0.0024 (9)	−0.0074 (9)

Geometric parameters (Å, º)

N1—C7	1.380 (2)	C10—C11	1.365 (3)
N1—C1	1.383 (2)	C10—H10	0.95
N1—C13	1.462 (2)	C11—C12	1.369 (3)
N2—C7	1.323 (2)	C11—H11	0.95
N2—C2	1.393 (2)	C12—H12	0.95
N3—C8	1.339 (3)	C13—C14	1.508 (3)
N3—C12	1.343 (3)	C13—H13A	0.99
N4—C18	1.335 (3)	C13—H13B	0.99
N4—C14	1.342 (2)	C14—C15	1.391 (3)
C1—C2	1.397 (2)	C15—C16	1.382 (3)
C1—C6	1.397 (3)	C15—H15	0.95
C2—C3	1.401 (3)	C16—C17	1.373 (3)
C3—C4	1.390 (3)	C16—H16	0.95
C3—H3	0.95	C17—C18	1.379 (3)
C4—C5	1.425 (3)	C17—H17	0.95
C4—C41	1.508 (3)	C18—H18	0.95
C5—C6	1.388 (3)	C41—H41A	0.98
C5—C51	1.509 (3)	C41—H41B	0.98
C6—H6	0.95	C41—H41C	0.98
C7—C8	1.480 (3)	C51—H51A	0.98
C8—C9	1.384 (3)	C51—H51B	0.98
C9—C10	1.380 (3)	C51—H51C	0.98
C9—H9	0.95
C7—N1—C1	106.25 (15)	C12—C11—H11	121.0
C7—N1—C13	129.76 (16)	N3—C12—C11	124.5 (2)
C1—N1—C13	123.79 (15)	N3—C12—H12	117.7
C7—N2—C2	104.84 (15)	C11—C12—H12	117.7
C8—N3—C12	116.53 (18)	N1—C13—C14	112.74 (15)
C18—N4—C14	116.94 (17)	N1—C13—H13A	109.0
N1—C1—C2	105.94 (15)	C14—C13—H13A	109.0
N1—C1—C6	131.78 (17)	N1—C13—H13B	109.0
C2—C1—C6	122.28 (17)	C14—C13—H13B	109.0
N2—C2—C1	110.03 (16)	H13A—C13—H13B	107.8
N2—C2—C3	130.31 (17)	N4—C14—C15	122.80 (17)
C1—C2—C3	119.66 (17)	N4—C14—C13	117.83 (16)
C4—C3—C2	119.05 (17)	C15—C14—C13	119.34 (16)
C4—C3—H3	120.5	C16—C15—C14	118.71 (19)
C2—C3—H3	120.5	C16—C15—H15	120.6
C3—C4—C5	120.51 (17)	C14—C15—H15	120.6
C3—C4—C41	119.39 (18)	C17—C16—C15	119.02 (19)
C5—C4—C41	120.10 (18)	C17—C16—H16	120.5
C6—C5—C4	120.56 (17)	C15—C16—H16	120.5
C6—C5—C51	119.54 (19)	C16—C17—C18	118.47 (19)
C4—C5—C51	119.89 (18)	C16—C17—H17	120.8
C5—C6—C1	117.94 (18)	C18—C17—H17	120.8
C5—C6—H6	121.0	N4—C18—C17	124.1 (2)
C1—C6—H6	121.0	N4—C18—H18	118.0
N2—C7—N1	112.94 (16)	C17—C18—H18	118.0
N2—C7—C8	121.86 (16)	C4—C41—H41A	109.5
N1—C7—C8	125.18 (16)	C4—C41—H41B	109.5
N3—C8—C9	122.61 (18)	H41A—C41—H41B	109.5
N3—C8—C7	118.58 (16)	C4—C41—H41C	109.5
C9—C8—C7	118.79 (17)	H41A—C41—H41C	109.5
C10—C9—C8	118.9 (2)	H41B—C41—H41C	109.5
C10—C9—H9	120.6	C5—C51—H51A	109.5
C8—C9—H9	120.6	C5—C51—H51B	109.5
C11—C10—C9	119.4 (2)	H51A—C51—H51B	109.5
C11—C10—H10	120.3	C5—C51—H51C	109.5
C9—C10—H10	120.3	H51A—C51—H51C	109.5
C10—C11—C12	118.1 (2)	H51B—C51—H51C	109.5
C10—C11—H11	121.0
C7—N1—C1—C2	0.21 (19)	C1—N1—C7—C8	−179.01 (16)
C13—N1—C1—C2	175.47 (15)	C13—N1—C7—C8	6.1 (3)
C7—N1—C1—C6	179.90 (19)	C12—N3—C8—C9	0.0 (3)
C13—N1—C1—C6	−4.8 (3)	C12—N3—C8—C7	178.3 (2)
C7—N2—C2—C1	−0.57 (19)	N2—C7—C8—N3	−147.33 (19)
C7—N2—C2—C3	179.25 (19)	N1—C7—C8—N3	30.9 (3)
N1—C1—C2—N2	0.2 (2)	N2—C7—C8—C9	31.1 (3)
C6—C1—C2—N2	−179.51 (16)	N1—C7—C8—C9	−150.64 (19)
N1—C1—C2—C3	−179.63 (16)	N3—C8—C9—C10	1.1 (3)
C6—C1—C2—C3	0.6 (3)	C7—C8—C9—C10	−177.28 (19)
N2—C2—C3—C4	179.31 (18)	C8—C9—C10—C11	−1.3 (4)
C1—C2—C3—C4	−0.9 (3)	C9—C10—C11—C12	0.4 (4)
C2—C3—C4—C5	0.2 (3)	C8—N3—C12—C11	−0.9 (4)
C2—C3—C4—C41	−178.91 (18)	C10—C11—C12—N3	0.7 (5)
C3—C4—C5—C6	0.8 (3)	C7—N1—C13—C14	114.6 (2)
C41—C4—C5—C6	179.87 (18)	C1—N1—C13—C14	−59.5 (2)
C3—C4—C5—C51	−178.65 (18)	C18—N4—C14—C15	0.2 (3)
C41—C4—C5—C51	0.5 (3)	C18—N4—C14—C13	−177.67 (18)
C4—C5—C6—C1	−1.0 (3)	N1—C13—C14—N4	−46.8 (2)
C51—C5—C6—C1	178.42 (17)	N1—C13—C14—C15	135.30 (18)
N1—C1—C6—C5	−179.34 (18)	N4—C14—C15—C16	−0.9 (3)
C2—C1—C6—C5	0.3 (3)	C13—C14—C15—C16	176.88 (17)
C2—N2—C7—N1	0.73 (19)	C14—C15—C16—C17	0.8 (3)
C2—N2—C7—C8	179.19 (16)	C15—C16—C17—C18	0.0 (3)
C1—N1—C7—N2	−0.6 (2)	C14—N4—C18—C17	0.7 (3)
C13—N1—C7—N2	−175.49 (16)	C16—C17—C18—N4	−0.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···N3	0.99	2.34	3.052 (3)	128
C13—H13B···N2^i	0.99	2.56	3.549 (2)	173
C11—H11···N4^ii	0.95	2.67	3.402 (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

Crystal data

C20H18N4	Z = 2
Mr = 314.38	F(000) = 332
Triclinic, P1	Dx = 1.256 Mg m^−3
a = 6.1920 (18) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.214 (3) Å	Cell parameters from 3700 reflections
c = 16.488 (5) Å	θ = 2.5–25.2°
α = 85.335 (9)°	µ = 0.08 mm^−1
β = 85.257 (9)°	T = 200 K
γ = 85.774 (9)°	Block, colourless
V = 831.1 (4) Å^3	0.50 × 0.40 × 0.40 mm

Data collection

Bruker SMART X2S benchtop diffractometer	2964 independent reflections
Radiation source: sealed microfocus tube	2061 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.074
Detector resolution: 8.3330 pixels mm^-1	θmax = 25.4°, θmin = 2.5°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −9→9
Tmin = 0.40, Tmax = 0.97	l = −19→19
9072 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.196	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.1081P)^2 + 0.0053P] where P = (Fo^2 + 2Fc^2)/3
2964 reflections	(Δ/σ)max < 0.001
219 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.7259 (3)	0.6674 (2)	0.73758 (10)	0.0383 (5)
N2	0.3894 (3)	0.7900 (2)	0.75758 (11)	0.0396 (5)
N3	0.7628 (4)	0.6764 (3)	0.91370 (13)	0.0646 (7)
N4	1.0980 (3)	0.3080 (2)	0.78326 (12)	0.0508 (6)
C1	0.6457 (4)	0.6990 (2)	0.66084 (13)	0.0383 (5)
C2	0.4390 (3)	0.7756 (2)	0.67451 (13)	0.0373 (5)
C3	0.3137 (4)	0.8233 (2)	0.60796 (13)	0.0418 (6)
H3	0.1729	0.876	0.6167	0.05*
C4	0.3974 (4)	0.7929 (3)	0.52988 (14)	0.0438 (6)
C5	0.6089 (4)	0.7137 (3)	0.51690 (13)	0.0449 (6)
C6	0.7334 (4)	0.6674 (3)	0.58233 (13)	0.0429 (6)
H6	0.8748	0.6155	0.5739	0.052*
C7	0.5631 (4)	0.7234 (2)	0.79296 (13)	0.0379 (5)
C8	0.5730 (4)	0.7172 (3)	0.88284 (13)	0.0421 (6)
C9	0.3867 (5)	0.7563 (4)	0.93111 (16)	0.0661 (8)
H9	0.2536	0.7853	0.9071	0.079*
C10	0.3954 (5)	0.7529 (4)	1.01471 (17)	0.0779 (9)
H10	0.2687	0.78	1.0488	0.094*
C11	0.5898 (5)	0.7097 (4)	1.04777 (17)	0.0699 (8)
H11	0.6006	0.7044	1.1051	0.084*
C12	0.7664 (5)	0.6748 (4)	0.99578 (17)	0.0776 (9)
H12	0.9014	0.6474	1.0186	0.093*
C13	0.9315 (3)	0.5740 (2)	0.75159 (14)	0.0415 (5)
H13A	0.9894	0.6112	0.8006	0.05*
H13B	1.0371	0.5984	0.7045	0.05*
C14	0.9141 (3)	0.3904 (2)	0.76334 (11)	0.0341 (5)
C15	0.7271 (4)	0.3144 (3)	0.75338 (13)	0.0430 (6)
H15	0.5979	0.3768	0.7399	0.052*
C16	0.7326 (4)	0.1437 (3)	0.76353 (15)	0.0532 (7)
H16	0.6068	0.0881	0.7568	0.064*
C17	0.9217 (5)	0.0570 (3)	0.78328 (17)	0.0594 (7)
H17	0.9303	−0.0592	0.7899	0.071*
C18	1.0972 (4)	0.1431 (3)	0.79319 (18)	0.0626 (7)
H18	1.227	0.0831	0.808	0.075*
C41	0.2616 (5)	0.8433 (3)	0.45814 (15)	0.0595 (7)
H41A	0.1182	0.8887	0.4783	0.089*
H41B	0.2449	0.7474	0.4281	0.089*
H41C	0.3343	0.9263	0.4218	0.089*
C51	0.6995 (5)	0.6796 (3)	0.43136 (15)	0.0615 (7)
H51A	0.6106	0.6022	0.4094	0.092*
H51B	0.8493	0.6324	0.4329	0.092*
H51C	0.6973	0.782	0.3964	0.092*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0354 (10)	0.0353 (9)	0.0442 (11)	0.0030 (8)	−0.0070 (8)	−0.0041 (7)
N2	0.0354 (10)	0.0401 (10)	0.0430 (10)	0.0030 (8)	−0.0045 (8)	−0.0048 (8)
N3	0.0493 (13)	0.0950 (18)	0.0486 (13)	0.0060 (12)	−0.0111 (10)	−0.0023 (11)
N4	0.0348 (11)	0.0445 (11)	0.0732 (14)	0.0053 (9)	−0.0110 (10)	−0.0052 (9)
C1	0.0395 (12)	0.0327 (10)	0.0439 (12)	−0.0024 (9)	−0.0089 (10)	−0.0032 (9)
C2	0.0354 (12)	0.0310 (10)	0.0455 (12)	−0.0004 (9)	−0.0054 (9)	−0.0027 (8)
C3	0.0361 (12)	0.0419 (12)	0.0472 (13)	0.0023 (9)	−0.0086 (10)	−0.0018 (9)
C4	0.0455 (13)	0.0406 (12)	0.0463 (13)	−0.0035 (10)	−0.0083 (10)	−0.0038 (9)
C5	0.0477 (14)	0.0463 (12)	0.0421 (13)	−0.0075 (10)	−0.0040 (11)	−0.0069 (10)
C6	0.0360 (12)	0.0420 (12)	0.0503 (14)	0.0014 (10)	−0.0003 (10)	−0.0077 (10)
C7	0.0406 (12)	0.0302 (10)	0.0430 (12)	−0.0015 (9)	−0.0050 (10)	−0.0034 (8)
C8	0.0439 (13)	0.0388 (11)	0.0438 (13)	−0.0025 (10)	−0.0067 (10)	−0.0022 (9)
C9	0.0501 (16)	0.101 (2)	0.0465 (15)	0.0059 (15)	−0.0037 (12)	−0.0142 (14)
C10	0.0612 (19)	0.127 (3)	0.0450 (16)	0.0028 (18)	0.0001 (14)	−0.0171 (16)
C11	0.070 (2)	0.097 (2)	0.0450 (15)	−0.0091 (16)	−0.0113 (14)	−0.0073 (14)
C12	0.0594 (19)	0.123 (3)	0.0515 (17)	0.0037 (18)	−0.0186 (15)	−0.0059 (16)
C13	0.0323 (11)	0.0405 (12)	0.0524 (13)	−0.0010 (9)	−0.0087 (10)	−0.0039 (9)
C14	0.0333 (11)	0.0392 (11)	0.0298 (10)	0.0026 (9)	−0.0035 (8)	−0.0064 (8)
C15	0.0387 (12)	0.0453 (12)	0.0464 (13)	−0.0031 (10)	−0.0090 (10)	−0.0062 (9)
C16	0.0524 (15)	0.0480 (13)	0.0616 (16)	−0.0151 (12)	−0.0054 (12)	−0.0065 (11)
C17	0.0661 (18)	0.0353 (12)	0.0759 (18)	−0.0008 (12)	0.0003 (14)	−0.0073 (11)
C18	0.0472 (15)	0.0445 (14)	0.095 (2)	0.0114 (12)	−0.0123 (14)	−0.0031 (13)
C41	0.0582 (16)	0.0703 (17)	0.0516 (15)	−0.0034 (14)	−0.0174 (13)	−0.0017 (12)
C51	0.0617 (17)	0.0744 (18)	0.0489 (15)	−0.0021 (14)	0.0009 (13)	−0.0160 (13)

Geometric parameters (Å, º)

N1—C7	1.382 (3)	C10—C11	1.373 (4)
N1—C1	1.395 (3)	C10—H10	0.95
N1—C13	1.462 (3)	C11—C12	1.361 (5)
N2—C7	1.327 (3)	C11—H11	0.95
N2—C2	1.391 (3)	C12—H12	0.95
N3—C8	1.329 (3)	C13—C14	1.515 (3)
N3—C12	1.354 (3)	C13—H13A	0.99
N4—C14	1.332 (3)	C13—H13B	0.99
N4—C18	1.351 (3)	C14—C15	1.383 (3)
C1—C2	1.394 (3)	C15—C16	1.397 (3)
C1—C6	1.398 (3)	C15—H15	0.95
C2—C3	1.409 (3)	C16—C17	1.374 (4)
C3—C4	1.382 (3)	C16—H16	0.95
C3—H3	0.95	C17—C18	1.367 (4)
C4—C5	1.427 (3)	C17—H17	0.95
C4—C41	1.520 (3)	C18—H18	0.95
C5—C6	1.389 (3)	C41—H41A	0.98
C5—C51	1.514 (3)	C41—H41B	0.98
C6—H6	0.95	C41—H41C	0.98
C7—C8	1.485 (3)	C51—H51A	0.98
C8—C9	1.379 (4)	C51—H51B	0.98
C9—C10	1.382 (4)	C51—H51C	0.98
C9—H9	0.95
C7—N1—C1	106.00 (18)	C10—C11—H11	121.1
C7—N1—C13	129.92 (18)	N3—C12—C11	124.5 (3)
C1—N1—C13	123.64 (18)	N3—C12—H12	117.8
C7—N2—C2	104.97 (18)	C11—C12—H12	117.8
C8—N3—C12	116.8 (2)	N1—C13—C14	114.18 (17)
C14—N4—C18	117.16 (19)	N1—C13—H13A	108.7
C2—C1—N1	105.85 (19)	C14—C13—H13A	108.7
C2—C1—C6	121.71 (19)	N1—C13—H13B	108.7
N1—C1—C6	132.4 (2)	C14—C13—H13B	108.7
N2—C2—C1	110.30 (17)	H13A—C13—H13B	107.6
N2—C2—C3	130.0 (2)	N4—C14—C15	122.83 (19)
C1—C2—C3	119.7 (2)	N4—C14—C13	113.50 (18)
C4—C3—C2	119.5 (2)	C15—C14—C13	123.66 (19)
C4—C3—H3	120.3	C14—C15—C16	118.5 (2)
C2—C3—H3	120.3	C14—C15—H15	120.8
C3—C4—C5	120.2 (2)	C16—C15—H15	120.8
C3—C4—C41	119.5 (2)	C17—C16—C15	119.3 (2)
C5—C4—C41	120.3 (2)	C17—C16—H16	120.3
C6—C5—C4	120.5 (2)	C15—C16—H16	120.3
C6—C5—C51	119.5 (2)	C18—C17—C16	118.0 (2)
C4—C5—C51	120.1 (2)	C18—C17—H17	121.0
C5—C6—C1	118.5 (2)	C16—C17—H17	121.0
C5—C6—H6	120.8	N4—C18—C17	124.2 (2)
C1—C6—H6	120.8	N4—C18—H18	117.9
N2—C7—N1	112.87 (19)	C17—C18—H18	117.9
N2—C7—C8	121.1 (2)	C4—C41—H41A	109.5
N1—C7—C8	126.0 (2)	C4—C41—H41B	109.5
N3—C8—C9	122.4 (2)	H41A—C41—H41B	109.5
N3—C8—C7	118.5 (2)	C4—C41—H41C	109.5
C9—C8—C7	119.1 (2)	H41A—C41—H41C	109.5
C8—C9—C10	119.4 (3)	H41B—C41—H41C	109.5
C8—C9—H9	120.3	C5—C51—H51A	109.5
C10—C9—H9	120.3	C5—C51—H51B	109.5
C11—C10—C9	119.0 (3)	H51A—C51—H51B	109.5
C11—C10—H10	120.5	C5—C51—H51C	109.5
C9—C10—H10	120.5	H51A—C51—H51C	109.5
C12—C11—C10	117.8 (3)	H51B—C51—H51C	109.5
C12—C11—H11	121.1
C7—N1—C1—C2	1.1 (2)	C1—N1—C7—C8	−179.70 (18)
C13—N1—C1—C2	174.10 (17)	C13—N1—C7—C8	7.9 (3)
C7—N1—C1—C6	−178.6 (2)	C12—N3—C8—C9	0.0 (4)
C13—N1—C1—C6	−5.6 (3)	C12—N3—C8—C7	178.9 (2)
C7—N2—C2—C1	0.0 (2)	N2—C7—C8—N3	−168.1 (2)
C7—N2—C2—C3	179.0 (2)	N1—C7—C8—N3	10.3 (3)
N1—C1—C2—N2	−0.7 (2)	N2—C7—C8—C9	10.8 (3)
C6—C1—C2—N2	179.01 (18)	N1—C7—C8—C9	−170.8 (2)
N1—C1—C2—C3	−179.85 (17)	N3—C8—C9—C10	−0.3 (4)
C6—C1—C2—C3	−0.1 (3)	C7—C8—C9—C10	−179.1 (2)
N2—C2—C3—C4	−178.70 (19)	C8—C9—C10—C11	−0.3 (5)
C1—C2—C3—C4	0.2 (3)	C9—C10—C11—C12	1.1 (5)
C2—C3—C4—C5	0.0 (3)	C8—N3—C12—C11	0.9 (5)
C2—C3—C4—C41	179.58 (19)	C10—C11—C12—N3	−1.4 (5)
C3—C4—C5—C6	−0.4 (3)	C7—N1—C13—C14	85.2 (2)
C41—C4—C5—C6	−180.0 (2)	C1—N1—C13—C14	−86.0 (2)
C3—C4—C5—C51	179.60 (19)	C18—N4—C14—C15	0.5 (3)
C41—C4—C5—C51	0.1 (3)	C18—N4—C14—C13	−178.7 (2)
C4—C5—C6—C1	0.5 (3)	N1—C13—C14—N4	−174.33 (17)
C51—C5—C6—C1	−179.49 (19)	N1—C13—C14—C15	6.5 (3)
C2—C1—C6—C5	−0.3 (3)	N4—C14—C15—C16	−0.9 (3)
N1—C1—C6—C5	179.4 (2)	C13—C14—C15—C16	178.1 (2)
C2—N2—C7—N1	0.7 (2)	C14—C15—C16—C17	0.3 (4)
C2—N2—C7—C8	179.33 (17)	C15—C16—C17—C18	0.8 (4)
C1—N1—C7—N2	−1.2 (2)	C14—N4—C18—C17	0.7 (4)
C13—N1—C7—N2	−173.57 (18)	C16—C17—C18—N4	−1.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···N3	0.99	2.31	2.953 (3)	121
C18—H18···N2^i	0.95	2.71	3.370 (3)	127
C11—H11···N4^ii	0.95	2.72	3.508 (3)	141

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