Synthesis, crystal structure studies and solvatochromic behaviour of two 2-{5-[4-(di­methyl­amino)­phen­yl]penta-2,4-dien-1-yl­idene}malono­nitrile derivatives

The synthesis, crystal structure studies and solvatochromic behavior of 2-{(2E,4E)-5-[4-(di­methyl­amino)­phen­yl]penta-2,4-dien-1-yl­idene}malono­nitrile, C₁₆H₁₅N₃ (DCV[3]), and 2-{(2E,4E,6E)-7-[4-(di­methyl­amino)­phen­yl]hepta-2,4,6-trien-1-yl­idene}malono­nitrile, C₁₈H₁₇N₃ (DCV[4]), are reported and dis­cussed in comparison with their homologs having a shorter length of the π-con­jugated bridge. The compounds of this series have potential use as non­linear materials with second-order effects due to their donor–acceptor structures. However, DCV[3] and DCV[4] crystallized in the centrosymmetric space group P2₁/c which excludes their application as nonlinear optical materials in the crystalline state. They both crystallize with two independent mol­ecules having the same mol­ecular conformation in the asymmetric unit. The series DCV[1]–DCV[4] demonstrated reversed solvatochromic behavior in toluene, chloro­form, and aceto­nitrile.

Computing details

Data collection: CrysAlis PRO (Agilent, 2012) for DCV3; APEX3 (Bruker, 2016) for DCV4. For both structures, cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT2017 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: Mercury (Macrae et al., 2008).

2-{5-[4-(Dimethylamino)phenyl]penta-2,4-dien-1-ylidene}malononitrile (DCV3)

Crystal data

C16H15N3	F(000) = 1056
Mr = 249.31	Dx = 1.179 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 16.9417 (3) Å	Cell parameters from 11249 reflections
b = 7.45114 (13) Å	θ = 3.7–73.5°
c = 23.0287 (4) Å	µ = 0.56 mm^−1
β = 104.9826 (18)°	T = 100 K
V = 2808.20 (9) Å^3	Plate, red
Z = 8	0.35 × 0.14 × 0.02 mm

Data collection

Agilent SuperNova Dual Source diffractometer with an Atlas detector	4914 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube	Rint = 0.028
ω scans	θmax = 73.7°, θmin = 4.0°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	h = −20→21
Tmin = 0.584, Tmax = 1.000	k = −9→8
27221 measured reflections	l = −28→28
5596 independent reflections

Refinement

Refinement on F^2	Primary atom site location: difference Fourier map
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0561P)^2 + 0.6844P] where P = (Fo^2 + 2Fc^2)/3
5596 reflections	(Δ/σ)max = 0.001
347 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.23 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. The single-crystal X-ray diffraction data for DCV[3] and DCV[4] were collected on a Bruker SMART APEX II CCD diffractometer (l(MoK_a)-radiation, graphite monochromator, w and f scan mode) and corrected for absorption using the SADABS program (Bruker, 2016). For details, see Table 4. The structures were solved by the intrinsic phasing modification of direct methods (Sheldrick, 2015a) and refined by a full-matrix least square technique on F² in anisotropic approximation for non-hydrogen atoms. The hydrogen atoms were placed in calculated positions and refined within the riding model with fixed isotropic displacement parameters [U_iso(H) = 1.5U_eq(C) for the methyl groups and 1.2U_eq(C) for the other groups]. All calculations were carried out using the SHELXTL program suite (Sheldrick, 2015b). The supplementary crystallographic data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N2A	0.06248 (7)	0.8003 (2)	0.48608 (6)	0.0575 (4)
N3A	0.28508 (6)	0.54591 (15)	0.46014 (5)	0.0345 (2)
N4A	0.82798 (5)	0.68629 (13)	0.88289 (4)	0.0245 (2)
C1A	0.21600 (6)	0.73520 (15)	0.52699 (5)	0.0244 (2)
C2A	0.13074 (7)	0.77210 (18)	0.50416 (6)	0.0349 (3)
C3A	0.25380 (6)	0.63146 (15)	0.48927 (5)	0.0257 (2)
C4A	0.75054 (6)	0.72307 (14)	0.84932 (5)	0.0211 (2)
C5A	0.69207 (6)	0.79987 (14)	0.87596 (5)	0.0216 (2)
H5A	0.706959	0.828252	0.917595	0.026*
C6A	0.61369 (6)	0.83398 (14)	0.84213 (5)	0.0219 (2)
H6A	0.575881	0.886870	0.861154	0.026*
C7A	0.58766 (6)	0.79341 (14)	0.78057 (5)	0.0212 (2)
C8A	0.64632 (6)	0.71854 (14)	0.75399 (5)	0.0228 (2)
H8A	0.631024	0.690352	0.712348	0.027*
C9A	0.72528 (6)	0.68516 (14)	0.78684 (5)	0.0233 (2)
H9A	0.763399	0.636009	0.767350	0.028*
C10A	0.85402 (7)	0.74330 (18)	0.94531 (5)	0.0297 (3)
H10A	0.852240	0.874562	0.947330	0.044*
H10B	0.909967	0.701822	0.963037	0.044*
H10C	0.817418	0.691944	0.967642	0.044*
C11A	0.89075 (6)	0.62695 (17)	0.85434 (5)	0.0296 (3)
H11A	0.871072	0.521883	0.829159	0.044*
H11B	0.940306	0.595055	0.885314	0.044*
H11C	0.903123	0.723971	0.829343	0.044*
C12A	0.25913 (6)	0.79560 (14)	0.58191 (5)	0.0236 (2)
H12A	0.230592	0.863249	0.604962	0.028*
C13A	0.34346 (6)	0.76451 (15)	0.60694 (5)	0.0227 (2)
H13A	0.373680	0.704052	0.583396	0.027*
C14A	0.38286 (6)	0.81798 (14)	0.66348 (5)	0.0229 (2)
H14A	0.352602	0.882770	0.686008	0.027*
C15A	0.46695 (6)	0.78243 (14)	0.69089 (5)	0.0231 (2)
H15A	0.498461	0.724196	0.667806	0.028*
C16A	0.50382 (6)	0.82815 (14)	0.74843 (5)	0.0224 (2)
H16A	0.471131	0.889509	0.769931	0.027*
N2B	0.72618 (6)	0.93541 (15)	0.54055 (4)	0.0327 (2)
N3B	0.52014 (6)	0.62185 (14)	0.57039 (4)	0.0311 (2)
N4B	−0.05174 (6)	0.75728 (15)	0.15912 (4)	0.0318 (2)
C1B	0.57868 (6)	0.81905 (15)	0.49907 (5)	0.0233 (2)
C2B	0.66068 (6)	0.88348 (15)	0.52181 (5)	0.0257 (2)
C3B	0.54730 (6)	0.70875 (15)	0.53908 (5)	0.0247 (2)
C4B	0.02901 (6)	0.77346 (15)	0.18858 (5)	0.0239 (2)
C5B	0.08427 (7)	0.86370 (16)	0.16212 (5)	0.0269 (2)
H5B	0.065020	0.914725	0.123211	0.032*
C6B	0.16570 (7)	0.87872 (15)	0.19195 (5)	0.0257 (2)
H6B	0.201216	0.939349	0.172628	0.031*
C7B	0.19836 (6)	0.80834 (14)	0.24960 (5)	0.0225 (2)
C8B	0.14345 (7)	0.71632 (15)	0.27566 (5)	0.0248 (2)
H8B	0.163285	0.664412	0.314380	0.030*
C9B	0.06173 (7)	0.69944 (15)	0.24660 (5)	0.0256 (2)
H9B	0.026616	0.636962	0.265806	0.031*
C10B	−0.08223 (8)	0.8355 (2)	0.09998 (6)	0.0443 (3)
H10D	−0.073492	0.965625	0.102372	0.067*
H10E	−0.140778	0.810377	0.085156	0.067*
H10F	−0.053054	0.783531	0.072392	0.067*
C11B	−0.10912 (8)	0.6717 (2)	0.18611 (6)	0.0450 (4)
H11D	−0.088805	0.552333	0.200560	0.067*
H11E	−0.161843	0.659886	0.156271	0.067*
H11F	−0.115976	0.744148	0.219980	0.067*
C12B	0.53196 (6)	0.86280 (15)	0.44324 (5)	0.0236 (2)
H12B	0.556126	0.935891	0.418722	0.028*
C13B	0.44978 (6)	0.80712 (15)	0.41902 (5)	0.0239 (2)
H13B	0.423801	0.738391	0.443515	0.029*
C14B	0.40695 (6)	0.84864 (15)	0.36204 (5)	0.0246 (2)
H14B	0.433744	0.916488	0.337859	0.030*
C15B	0.32412 (6)	0.79638 (15)	0.33637 (5)	0.0249 (2)
H15B	0.296749	0.727550	0.359934	0.030*
C16B	0.28335 (6)	0.84161 (15)	0.27966 (5)	0.0243 (2)
H16B	0.314240	0.902680	0.256732	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N2A	0.0236 (6)	0.0747 (10)	0.0646 (8)	0.0071 (6)	−0.0060 (5)	−0.0144 (7)
N3A	0.0345 (5)	0.0348 (6)	0.0351 (5)	−0.0030 (4)	0.0104 (4)	−0.0033 (5)
N4A	0.0171 (4)	0.0298 (5)	0.0251 (4)	0.0004 (4)	0.0025 (3)	−0.0020 (4)
C1A	0.0171 (5)	0.0246 (6)	0.0294 (5)	−0.0005 (4)	0.0026 (4)	0.0021 (4)
C2A	0.0233 (6)	0.0393 (7)	0.0380 (6)	0.0004 (5)	0.0004 (5)	−0.0057 (5)
C3A	0.0217 (5)	0.0260 (6)	0.0270 (5)	−0.0042 (4)	0.0017 (4)	0.0020 (4)
C4A	0.0183 (5)	0.0186 (5)	0.0253 (5)	−0.0026 (4)	0.0039 (4)	0.0008 (4)
C5A	0.0208 (5)	0.0212 (5)	0.0218 (5)	−0.0030 (4)	0.0038 (4)	−0.0011 (4)
C6A	0.0204 (5)	0.0197 (5)	0.0259 (5)	−0.0013 (4)	0.0064 (4)	−0.0006 (4)
C7A	0.0201 (5)	0.0180 (5)	0.0242 (5)	−0.0023 (4)	0.0033 (4)	0.0010 (4)
C8A	0.0227 (5)	0.0225 (5)	0.0221 (5)	−0.0024 (4)	0.0037 (4)	−0.0009 (4)
C9A	0.0212 (5)	0.0224 (5)	0.0264 (5)	−0.0015 (4)	0.0064 (4)	−0.0018 (4)
C10A	0.0209 (5)	0.0379 (7)	0.0273 (5)	−0.0001 (5)	0.0010 (4)	−0.0042 (5)
C11A	0.0201 (5)	0.0344 (6)	0.0328 (6)	0.0042 (5)	0.0043 (4)	−0.0044 (5)
C12A	0.0208 (5)	0.0211 (5)	0.0285 (5)	0.0004 (4)	0.0057 (4)	0.0021 (4)
C13A	0.0196 (5)	0.0210 (5)	0.0266 (5)	−0.0001 (4)	0.0044 (4)	0.0012 (4)
C14A	0.0208 (5)	0.0199 (5)	0.0271 (5)	−0.0002 (4)	0.0048 (4)	0.0017 (4)
C15A	0.0205 (5)	0.0218 (5)	0.0260 (5)	0.0000 (4)	0.0040 (4)	0.0013 (4)
C16A	0.0210 (5)	0.0194 (5)	0.0265 (5)	−0.0007 (4)	0.0057 (4)	0.0016 (4)
N2B	0.0248 (5)	0.0355 (6)	0.0355 (5)	−0.0016 (4)	0.0040 (4)	0.0029 (4)
N3B	0.0314 (5)	0.0312 (5)	0.0329 (5)	0.0020 (4)	0.0121 (4)	0.0001 (4)
N4B	0.0233 (5)	0.0413 (6)	0.0277 (5)	−0.0034 (4)	0.0008 (4)	0.0043 (4)
C1B	0.0197 (5)	0.0226 (5)	0.0280 (5)	0.0005 (4)	0.0070 (4)	−0.0026 (4)
C2B	0.0245 (5)	0.0257 (6)	0.0272 (5)	0.0026 (4)	0.0074 (4)	0.0010 (4)
C3B	0.0213 (5)	0.0257 (6)	0.0265 (5)	0.0023 (4)	0.0048 (4)	−0.0039 (4)
C4B	0.0230 (5)	0.0229 (5)	0.0244 (5)	0.0004 (4)	0.0036 (4)	−0.0017 (4)
C5B	0.0291 (6)	0.0262 (6)	0.0235 (5)	−0.0010 (4)	0.0036 (4)	0.0033 (4)
C6B	0.0275 (5)	0.0238 (6)	0.0264 (5)	−0.0034 (4)	0.0082 (4)	0.0011 (4)
C7B	0.0232 (5)	0.0200 (5)	0.0241 (5)	0.0005 (4)	0.0058 (4)	−0.0012 (4)
C8B	0.0241 (5)	0.0266 (6)	0.0230 (5)	0.0002 (4)	0.0047 (4)	0.0026 (4)
C9B	0.0244 (5)	0.0281 (6)	0.0247 (5)	−0.0024 (4)	0.0068 (4)	0.0019 (4)
C10B	0.0299 (6)	0.0613 (9)	0.0343 (6)	−0.0056 (6)	−0.0052 (5)	0.0126 (6)
C11B	0.0246 (6)	0.0655 (10)	0.0409 (7)	−0.0092 (6)	0.0016 (5)	0.0135 (7)
C12B	0.0228 (5)	0.0214 (5)	0.0278 (5)	0.0016 (4)	0.0087 (4)	−0.0022 (4)
C13B	0.0218 (5)	0.0222 (5)	0.0283 (5)	0.0007 (4)	0.0077 (4)	−0.0018 (4)
C14B	0.0230 (5)	0.0228 (5)	0.0287 (5)	0.0002 (4)	0.0080 (4)	−0.0015 (4)
C15B	0.0225 (5)	0.0242 (6)	0.0281 (5)	−0.0003 (4)	0.0069 (4)	−0.0002 (4)
C16B	0.0233 (5)	0.0218 (5)	0.0286 (5)	−0.0009 (4)	0.0081 (4)	−0.0013 (4)

Geometric parameters (Å, º)

N2A—C2A	1.1429 (16)	N2B—C2B	1.1488 (14)
N3A—C3A	1.1493 (15)	N3B—C3B	1.1499 (15)
N4A—C4A	1.3673 (13)	N4B—C4B	1.3663 (14)
N4A—C10A	1.4538 (14)	N4B—C11B	1.4321 (16)
N4A—C11A	1.4560 (13)	N4B—C10B	1.4483 (15)
C1A—C12A	1.3631 (15)	C1B—C12B	1.3637 (15)
C1A—C2A	1.4304 (15)	C1B—C2B	1.4348 (14)
C1A—C3A	1.4317 (16)	C1B—C3B	1.4354 (15)
C4A—C5A	1.4140 (14)	C4B—C5B	1.4124 (15)
C4A—C9A	1.4195 (14)	C4B—C9B	1.4189 (15)
C5A—C6A	1.3785 (14)	C5B—C6B	1.3775 (15)
C5A—H5A	0.9500	C5B—H5B	0.9500
C6A—C7A	1.4044 (14)	C6B—C7B	1.4014 (15)
C6A—H6A	0.9500	C6B—H6B	0.9500
C7A—C8A	1.4099 (15)	C7B—C8B	1.4087 (15)
C7A—C16A	1.4453 (14)	C7B—C16B	1.4487 (14)
C8A—C9A	1.3786 (14)	C8B—C9B	1.3789 (15)
C8A—H8A	0.9500	C8B—H8B	0.9500
C9A—H9A	0.9500	C9B—H9B	0.9500
C10A—H10A	0.9800	C10B—H10D	0.9800
C10A—H10B	0.9800	C10B—H10E	0.9800
C10A—H10C	0.9800	C10B—H10F	0.9800
C11A—H11A	0.9800	C11B—H11D	0.9800
C11A—H11B	0.9800	C11B—H11E	0.9800
C11A—H11C	0.9800	C11B—H11F	0.9800
C12A—C13A	1.4146 (14)	C12B—C13B	1.4213 (14)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—C14A	1.3603 (15)	C13B—C14B	1.3609 (15)
C13A—H13A	0.9500	C13B—H13B	0.9500
C14A—C15A	1.4260 (14)	C14B—C15B	1.4287 (14)
C14A—H14A	0.9500	C14B—H14B	0.9500
C15A—C16A	1.3543 (15)	C15B—C16B	1.3528 (15)
C15A—H15A	0.9500	C15B—H15B	0.9500
C16A—H16A	0.9500	C16B—H16B	0.9500
C4A—N4A—C10A	120.13 (9)	C4B—N4B—C11B	121.91 (10)
C4A—N4A—C11A	120.78 (9)	C4B—N4B—C10B	119.96 (10)
C10A—N4A—C11A	117.70 (9)	C11B—N4B—C10B	118.06 (10)
C12A—C1A—C2A	121.72 (10)	C12B—C1B—C2B	122.37 (10)
C12A—C1A—C3A	121.64 (10)	C12B—C1B—C3B	121.41 (10)
C2A—C1A—C3A	116.64 (10)	C2B—C1B—C3B	116.20 (9)
N2A—C2A—C1A	179.47 (17)	N2B—C2B—C1B	179.34 (12)
N3A—C3A—C1A	178.40 (12)	N3B—C3B—C1B	178.21 (12)
N4A—C4A—C5A	120.88 (9)	N4B—C4B—C5B	121.20 (10)
N4A—C4A—C9A	121.80 (9)	N4B—C4B—C9B	122.05 (10)
C5A—C4A—C9A	117.31 (9)	C5B—C4B—C9B	116.75 (10)
C6A—C5A—C4A	120.66 (9)	C6B—C5B—C4B	120.90 (10)
C6A—C5A—H5A	119.7	C6B—C5B—H5B	119.6
C4A—C5A—H5A	119.7	C4B—C5B—H5B	119.6
C5A—C6A—C7A	122.41 (9)	C5B—C6B—C7B	122.77 (10)
C5A—C6A—H6A	118.8	C5B—C6B—H6B	118.6
C7A—C6A—H6A	118.8	C7B—C6B—H6B	118.6
C6A—C7A—C8A	116.79 (9)	C6B—C7B—C8B	116.32 (10)
C6A—C7A—C16A	119.26 (9)	C6B—C7B—C16B	119.26 (9)
C8A—C7A—C16A	123.94 (9)	C8B—C7B—C16B	124.33 (10)
C9A—C8A—C7A	121.74 (9)	C9B—C8B—C7B	121.89 (10)
C9A—C8A—H8A	119.1	C9B—C8B—H8B	119.1
C7A—C8A—H8A	119.1	C7B—C8B—H8B	119.1
C8A—C9A—C4A	121.05 (9)	C8B—C9B—C4B	121.36 (10)
C8A—C9A—H9A	119.5	C8B—C9B—H9B	119.3
C4A—C9A—H9A	119.5	C4B—C9B—H9B	119.3
N4A—C10A—H10A	109.5	N4B—C10B—H10D	109.5
N4A—C10A—H10B	109.5	N4B—C10B—H10E	109.5
H10A—C10A—H10B	109.5	H10D—C10B—H10E	109.5
N4A—C10A—H10C	109.5	N4B—C10B—H10F	109.5
H10A—C10A—H10C	109.5	H10D—C10B—H10F	109.5
H10B—C10A—H10C	109.5	H10E—C10B—H10F	109.5
N4A—C11A—H11A	109.5	N4B—C11B—H11D	109.5
N4A—C11A—H11B	109.5	N4B—C11B—H11E	109.5
H11A—C11A—H11B	109.5	H11D—C11B—H11E	109.5
N4A—C11A—H11C	109.5	N4B—C11B—H11F	109.5
H11A—C11A—H11C	109.5	H11D—C11B—H11F	109.5
H11B—C11A—H11C	109.5	H11E—C11B—H11F	109.5
C1A—C12A—C13A	124.52 (10)	C1B—C12B—C13B	124.82 (10)
C1A—C12A—H12A	117.7	C1B—C12B—H12B	117.6
C13A—C12A—H12A	117.7	C13B—C12B—H12B	117.6
C14A—C13A—C12A	122.42 (10)	C14B—C13B—C12B	122.42 (10)
C14A—C13A—H13A	118.8	C14B—C13B—H13B	118.8
C12A—C13A—H13A	118.8	C12B—C13B—H13B	118.8
C13A—C14A—C15A	123.79 (10)	C13B—C14B—C15B	123.98 (10)
C13A—C14A—H14A	118.1	C13B—C14B—H14B	118.0
C15A—C14A—H14A	118.1	C15B—C14B—H14B	118.0
C16A—C15A—C14A	122.79 (10)	C16B—C15B—C14B	122.22 (10)
C16A—C15A—H15A	118.6	C16B—C15B—H15B	118.9
C14A—C15A—H15A	118.6	C14B—C15B—H15B	118.9
C15A—C16A—C7A	126.83 (10)	C15B—C16B—C7B	127.95 (10)
C15A—C16A—H16A	116.6	C15B—C16B—H16B	116.0
C7A—C16A—H16A	116.6	C7B—C16B—H16B	116.0
C10A—N4A—C4A—C5A	−6.58 (16)	C11B—N4B—C4B—C5B	−177.81 (12)
C11A—N4A—C4A—C5A	−172.79 (10)	C10B—N4B—C4B—C5B	−0.83 (18)
C10A—N4A—C4A—C9A	173.84 (10)	C11B—N4B—C4B—C9B	2.91 (18)
C11A—N4A—C4A—C9A	7.64 (16)	C10B—N4B—C4B—C9B	179.89 (12)
N4A—C4A—C5A—C6A	−178.93 (10)	N4B—C4B—C5B—C6B	−179.66 (11)
C9A—C4A—C5A—C6A	0.67 (15)	C9B—C4B—C5B—C6B	−0.35 (16)
C4A—C5A—C6A—C7A	0.68 (16)	C4B—C5B—C6B—C7B	−0.58 (18)
C5A—C6A—C7A—C8A	−1.29 (16)	C5B—C6B—C7B—C8B	1.36 (16)
C5A—C6A—C7A—C16A	178.18 (10)	C5B—C6B—C7B—C16B	−175.39 (10)
C6A—C7A—C8A—C9A	0.54 (16)	C6B—C7B—C8B—C9B	−1.25 (16)
C16A—C7A—C8A—C9A	−178.89 (10)	C16B—C7B—C8B—C9B	175.31 (10)
C7A—C8A—C9A—C4A	0.79 (17)	C7B—C8B—C9B—C4B	0.38 (17)
N4A—C4A—C9A—C8A	178.20 (10)	N4B—C4B—C9B—C8B	179.75 (11)
C5A—C4A—C9A—C8A	−1.39 (16)	C5B—C4B—C9B—C8B	0.44 (16)
C2A—C1A—C12A—C13A	−179.71 (11)	C2B—C1B—C12B—C13B	−178.17 (10)
C3A—C1A—C12A—C13A	0.33 (17)	C3B—C1B—C12B—C13B	0.21 (17)
C1A—C12A—C13A—C14A	−175.85 (11)	C1B—C12B—C13B—C14B	−177.27 (10)
C12A—C13A—C14A—C15A	177.39 (10)	C12B—C13B—C14B—C15B	−179.43 (10)
C13A—C14A—C15A—C16A	−176.21 (10)	C13B—C14B—C15B—C16B	179.43 (11)
C14A—C15A—C16A—C7A	178.11 (10)	C14B—C15B—C16B—C7B	−175.48 (10)
C6A—C7A—C16A—C15A	−173.54 (10)	C6B—C7B—C16B—C15B	174.95 (11)
C8A—C7A—C16A—C15A	5.88 (18)	C8B—C7B—C16B—C15B	−1.52 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10A—H10B···N2A^i	0.98	2.50	3.4270 (16)	158

Symmetry code: (i) x+1, −y+3/2, z+1/2.

2-{(2E,4E,6E)-7-[4-(Dimethylamino)phenyl]hepta-2,4,6-trien-1-ylidene}malononitrile (DCV4)

Crystal data

C18H17N3	F(000) = 1168
Mr = 275.34	Dx = 1.205 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.6175 (16) Å	Cell parameters from 9945 reflections
b = 11.6514 (14) Å	θ = 4.2–30.6°
c = 19.723 (2) Å	µ = 0.07 mm^−1
β = 104.121 (2)°	T = 100 K
V = 3034.8 (6) Å^3	Block, black
Z = 8	0.30 × 0.20 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer	7413 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube	Rint = 0.028
φ and ω scans	θmax = 30.6°, θmin = 4.2°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −19→18
Tmin = 0.662, Tmax = 0.746	k = −16→16
35544 measured reflections	l = −28→28
9304 independent reflections

Refinement

Refinement on F^2	Primary atom site location: difference Fourier map
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.132	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0736P)^2 + 0.4714P] where P = (Fo^2 + 2Fc^2)/3
9304 reflections	(Δ/σ)max < 0.001
383 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.19 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. The single-crystal X-ray diffraction data for DCV[3] and DCV[4] were collected on a Bruker SMART APEX II CCD diffractometer (l(MoK_a)-radiation, graphite monochromator, w and f scan mode) and corrected for absorption using the SADABS program (Bruker, 2016). For details, see Table 4. The structures were solved by the intrinsic phasing modification of direct methods (Sheldrick, 2015a) and refined by a full-matrix least square technique on F² in anisotropic approximation for non-hydrogen atoms. The hydrogen atoms were placed in calculated positions and refined within the riding model with fixed isotropic displacement parameters [U_iso(H) = 1.5U_eq(C) for the methyl groups and 1.2U_eq(C) for the other groups]. All calculations were carried out using the SHELXTL program suite (Sheldrick, 2015b). The supplementary crystallographic data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N2A	−0.02331 (8)	0.44421 (8)	−0.39101 (5)	0.0317 (2)
N3A	−0.06996 (7)	0.08869 (8)	−0.33804 (5)	0.0297 (2)
N4A	0.36455 (7)	0.06076 (8)	0.42093 (4)	0.02794 (19)
C1A	−0.00139 (7)	0.28907 (8)	−0.29515 (5)	0.01924 (17)
C2A	−0.01432 (7)	0.37585 (8)	−0.34834 (5)	0.02232 (19)
C3A	−0.03914 (7)	0.17756 (8)	−0.31814 (5)	0.02093 (18)
C4A	0.33609 (7)	0.10499 (8)	0.35438 (5)	0.02077 (18)
C5A	0.36127 (7)	0.21805 (8)	0.33948 (5)	0.02148 (18)
H5A	0.397735	0.265699	0.376147	0.026*
C6A	0.33334 (7)	0.26013 (8)	0.27196 (5)	0.02029 (18)
H6A	0.351300	0.336616	0.263404	0.024*
C7A	0.27938 (7)	0.19396 (8)	0.21551 (5)	0.01866 (17)
C8A	0.25466 (7)	0.08140 (8)	0.23071 (5)	0.01990 (18)
H8A	0.218640	0.033881	0.193815	0.024*
C9A	0.28133 (7)	0.03790 (8)	0.29788 (5)	0.02089 (18)
H9A	0.262594	−0.038346	0.306288	0.025*
C10A	0.41401 (8)	0.13326 (10)	0.47894 (5)	0.0294 (2)
H10D	0.474122	0.168590	0.468738	0.044*
H10E	0.434254	0.086778	0.521481	0.044*
H10F	0.367098	0.193427	0.485829	0.044*
C11A	0.32290 (9)	−0.04831 (10)	0.43636 (6)	0.0304 (2)
H11D	0.248905	−0.046153	0.420393	0.046*
H11E	0.342409	−0.062091	0.486890	0.046*
H11F	0.349325	−0.110217	0.412201	0.046*
C12A	0.04484 (7)	0.31391 (8)	−0.22713 (5)	0.01997 (18)
H12A	0.065701	0.391128	−0.216952	0.024*
C13A	0.06481 (7)	0.23574 (8)	−0.17013 (5)	0.02033 (18)
H13A	0.045783	0.157425	−0.177487	0.024*
C14A	0.11140 (7)	0.27368 (8)	−0.10487 (5)	0.02087 (18)
H14A	0.129914	0.352427	−0.100313	0.025*
C15A	0.13488 (7)	0.20602 (9)	−0.04281 (5)	0.02173 (18)
H15A	0.118784	0.126550	−0.045646	0.026*
C16A	0.17979 (7)	0.25258 (8)	0.02036 (5)	0.02101 (18)
H16A	0.195829	0.332012	0.021376	0.025*
C17A	0.20493 (7)	0.19208 (8)	0.08542 (5)	0.02126 (18)
H17A	0.188683	0.112848	0.085991	0.026*
C18A	0.25116 (7)	0.24417 (8)	0.14627 (5)	0.02004 (18)
H18A	0.266975	0.323105	0.143151	0.024*
N2B	0.62142 (7)	0.34461 (8)	0.89338 (5)	0.02768 (19)
N3B	0.49051 (7)	0.68469 (8)	0.84150 (5)	0.02827 (19)
N4B	0.12933 (7)	0.71560 (8)	0.08610 (4)	0.02634 (18)
C1B	0.53305 (7)	0.48678 (8)	0.79738 (5)	0.02034 (18)
C2B	0.58224 (7)	0.40728 (8)	0.85038 (5)	0.02165 (18)
C3B	0.50958 (7)	0.59688 (8)	0.82144 (5)	0.02149 (19)
C4B	0.16278 (7)	0.67082 (9)	0.15183 (5)	0.02140 (18)
C5B	0.14792 (7)	0.55429 (9)	0.16558 (5)	0.02272 (19)
H5B	0.114020	0.505526	0.128647	0.027*
C6B	0.18219 (7)	0.51006 (9)	0.23233 (5)	0.02233 (19)
H6B	0.170750	0.431256	0.240099	0.027*
C7B	0.23323 (7)	0.57760 (8)	0.28891 (5)	0.02023 (18)
C8B	0.24749 (7)	0.69372 (9)	0.27485 (5)	0.02227 (19)
H8B	0.281596	0.742086	0.311937	0.027*
C9B	0.21347 (8)	0.73975 (9)	0.20879 (5)	0.02335 (19)
H9B	0.224220	0.818859	0.201434	0.028*
C10B	0.09193 (10)	0.64045 (11)	0.02686 (6)	0.0350 (3)
H10A	0.144904	0.585528	0.023213	0.053*
H10B	0.073202	0.686245	−0.016044	0.053*
H10C	0.032380	0.598765	0.033345	0.053*
C11B	0.14443 (10)	0.83608 (10)	0.07314 (6)	0.0335 (2)
H11A	0.112358	0.883169	0.102864	0.050*
H11B	0.114011	0.853685	0.023903	0.050*
H11C	0.217125	0.852801	0.083893	0.050*
C12B	0.50707 (7)	0.45684 (8)	0.72805 (5)	0.02137 (18)
H12B	0.521142	0.380423	0.716507	0.026*
C13B	0.46095 (7)	0.53063 (8)	0.67222 (5)	0.02143 (18)
H13B	0.449899	0.608963	0.681481	0.026*
C14B	0.43220 (7)	0.49035 (9)	0.60521 (5)	0.02216 (19)
H14B	0.441188	0.410833	0.597924	0.027*
C15B	0.38980 (7)	0.55889 (9)	0.54561 (5)	0.02263 (19)
H15B	0.387356	0.639755	0.551119	0.027*
C16B	0.35260 (7)	0.51304 (9)	0.48100 (5)	0.02246 (19)
H16B	0.353363	0.431793	0.477096	0.027*
C17B	0.31250 (7)	0.57682 (9)	0.41857 (5)	0.02308 (19)
H17B	0.315278	0.658265	0.420356	0.028*
C18B	0.27057 (7)	0.52474 (9)	0.35681 (5)	0.02193 (19)
H18B	0.264996	0.443550	0.358244	0.026*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N2A	0.0381 (5)	0.0275 (5)	0.0293 (5)	0.0030 (4)	0.0076 (4)	0.0066 (4)
N3A	0.0312 (5)	0.0239 (4)	0.0301 (5)	−0.0008 (4)	0.0002 (4)	0.0006 (3)
N4A	0.0356 (5)	0.0284 (4)	0.0167 (4)	0.0012 (4)	0.0005 (3)	0.0024 (3)
C1A	0.0199 (4)	0.0184 (4)	0.0190 (4)	0.0012 (3)	0.0038 (3)	0.0024 (3)
C2A	0.0234 (4)	0.0212 (4)	0.0220 (4)	0.0012 (3)	0.0049 (3)	0.0005 (3)
C3A	0.0209 (4)	0.0215 (4)	0.0188 (4)	0.0019 (3)	0.0018 (3)	0.0031 (3)
C4A	0.0204 (4)	0.0242 (5)	0.0170 (4)	0.0044 (3)	0.0030 (3)	0.0007 (3)
C5A	0.0218 (4)	0.0226 (4)	0.0186 (4)	0.0020 (3)	0.0022 (3)	−0.0027 (3)
C6A	0.0203 (4)	0.0193 (4)	0.0206 (4)	0.0004 (3)	0.0038 (3)	−0.0009 (3)
C7A	0.0183 (4)	0.0200 (4)	0.0170 (4)	0.0014 (3)	0.0030 (3)	−0.0001 (3)
C8A	0.0193 (4)	0.0204 (4)	0.0187 (4)	0.0000 (3)	0.0021 (3)	−0.0008 (3)
C9A	0.0211 (4)	0.0202 (4)	0.0206 (4)	0.0008 (3)	0.0037 (3)	0.0013 (3)
C10A	0.0304 (5)	0.0390 (6)	0.0168 (4)	0.0039 (4)	0.0019 (4)	−0.0019 (4)
C11A	0.0299 (5)	0.0368 (6)	0.0229 (5)	0.0001 (4)	0.0034 (4)	0.0093 (4)
C12A	0.0194 (4)	0.0202 (4)	0.0202 (4)	0.0000 (3)	0.0045 (3)	0.0006 (3)
C13A	0.0212 (4)	0.0200 (4)	0.0191 (4)	−0.0001 (3)	0.0036 (3)	0.0014 (3)
C14A	0.0210 (4)	0.0215 (4)	0.0195 (4)	−0.0013 (3)	0.0038 (3)	0.0000 (3)
C15A	0.0226 (4)	0.0219 (4)	0.0193 (4)	−0.0008 (3)	0.0023 (3)	0.0007 (3)
C16A	0.0219 (4)	0.0210 (4)	0.0192 (4)	−0.0007 (3)	0.0032 (3)	0.0012 (3)
C17A	0.0229 (4)	0.0203 (4)	0.0192 (4)	−0.0010 (3)	0.0025 (3)	0.0009 (3)
C18A	0.0208 (4)	0.0199 (4)	0.0186 (4)	−0.0006 (3)	0.0032 (3)	0.0011 (3)
N2B	0.0302 (4)	0.0273 (4)	0.0257 (4)	0.0031 (3)	0.0072 (3)	0.0022 (3)
N3B	0.0355 (5)	0.0237 (4)	0.0247 (4)	0.0007 (4)	0.0054 (4)	0.0013 (3)
N4B	0.0315 (4)	0.0287 (4)	0.0181 (4)	0.0007 (3)	0.0049 (3)	0.0014 (3)
C1B	0.0210 (4)	0.0200 (4)	0.0199 (4)	−0.0014 (3)	0.0048 (3)	0.0014 (3)
C2B	0.0221 (4)	0.0219 (4)	0.0218 (4)	−0.0012 (3)	0.0070 (3)	−0.0012 (3)
C3B	0.0229 (4)	0.0227 (4)	0.0181 (4)	−0.0024 (3)	0.0036 (3)	0.0023 (3)
C4B	0.0206 (4)	0.0252 (5)	0.0191 (4)	0.0015 (3)	0.0063 (3)	0.0000 (3)
C5B	0.0236 (4)	0.0232 (4)	0.0201 (4)	−0.0005 (4)	0.0030 (3)	−0.0033 (3)
C6B	0.0233 (4)	0.0202 (4)	0.0228 (4)	−0.0002 (3)	0.0044 (3)	−0.0017 (3)
C7B	0.0196 (4)	0.0219 (4)	0.0188 (4)	0.0015 (3)	0.0040 (3)	−0.0010 (3)
C8B	0.0230 (4)	0.0225 (4)	0.0208 (4)	−0.0014 (3)	0.0043 (3)	−0.0028 (3)
C9B	0.0261 (5)	0.0213 (4)	0.0226 (4)	−0.0017 (4)	0.0059 (4)	−0.0004 (3)
C10B	0.0445 (6)	0.0386 (6)	0.0199 (5)	0.0064 (5)	0.0038 (4)	−0.0045 (4)
C11B	0.0392 (6)	0.0330 (6)	0.0276 (5)	−0.0020 (5)	0.0070 (4)	0.0078 (4)
C12B	0.0220 (4)	0.0204 (4)	0.0219 (4)	−0.0027 (3)	0.0057 (3)	−0.0005 (3)
C13B	0.0238 (4)	0.0205 (4)	0.0198 (4)	−0.0019 (3)	0.0050 (3)	0.0002 (3)
C14B	0.0224 (4)	0.0235 (4)	0.0204 (4)	−0.0007 (3)	0.0050 (3)	0.0002 (3)
C15B	0.0242 (4)	0.0229 (4)	0.0206 (4)	−0.0007 (4)	0.0051 (3)	−0.0001 (3)
C16B	0.0237 (4)	0.0231 (4)	0.0203 (4)	0.0009 (4)	0.0049 (3)	0.0003 (3)
C17B	0.0250 (5)	0.0228 (4)	0.0211 (4)	0.0015 (4)	0.0050 (4)	0.0005 (3)
C18B	0.0225 (4)	0.0219 (4)	0.0209 (4)	0.0016 (3)	0.0042 (3)	0.0002 (3)

Geometric parameters (Å, º)

N2A—C2A	1.1435 (13)	N2B—C2B	1.1473 (13)
N3A—C3A	1.1497 (13)	N3B—C3B	1.1494 (13)
N4A—C4A	1.3750 (12)	N4B—C4B	1.3683 (12)
N4A—C10A	1.4492 (13)	N4B—C10B	1.4495 (14)
N4A—C11A	1.4538 (14)	N4B—C11B	1.4505 (14)
C1A—C12A	1.3668 (13)	C1B—C12B	1.3714 (13)
C1A—C3A	1.4298 (13)	C1B—C3B	1.4307 (14)
C1A—C2A	1.4366 (13)	C1B—C2B	1.4344 (13)
C4A—C5A	1.4101 (14)	C4B—C5B	1.4089 (14)
C4A—C9A	1.4154 (13)	C4B—C9B	1.4161 (13)
C5A—C6A	1.3827 (13)	C5B—C6B	1.3845 (13)
C5A—H5A	0.9500	C5B—H5B	0.9500
C6A—C7A	1.4053 (13)	C6B—C7B	1.4033 (13)
C6A—H6A	0.9500	C6B—H6B	0.9500
C7A—C8A	1.4045 (13)	C7B—C8B	1.4041 (14)
C7A—C18A	1.4486 (12)	C7B—C18B	1.4489 (13)
C8A—C9A	1.3817 (13)	C8B—C9B	1.3803 (13)
C8A—H8A	0.9500	C8B—H8B	0.9500
C9A—H9A	0.9500	C9B—H9B	0.9500
C10A—H10D	0.9800	C10B—H10A	0.9800
C10A—H10E	0.9800	C10B—H10B	0.9800
C10A—H10F	0.9800	C10B—H10C	0.9800
C11A—H11D	0.9800	C11B—H11A	0.9800
C11A—H11E	0.9800	C11B—H11B	0.9800
C11A—H11F	0.9800	C11B—H11C	0.9800
C12A—C13A	1.4206 (13)	C12B—C13B	1.4173 (13)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—C14A	1.3625 (13)	C13B—C14B	1.3667 (13)
C13A—H13A	0.9500	C13B—H13B	0.9500
C14A—C15A	1.4250 (13)	C14B—C15B	1.4218 (13)
C14A—H14A	0.9500	C14B—H14B	0.9500
C15A—C16A	1.3598 (13)	C15B—C16B	1.3605 (13)
C15A—H15A	0.9500	C15B—H15B	0.9500
C16A—C17A	1.4305 (13)	C16B—C17B	1.4278 (13)
C16A—H16A	0.9500	C16B—H16B	0.9500
C17A—C18A	1.3551 (13)	C17B—C18B	1.3559 (13)
C17A—H17A	0.9500	C17B—H17B	0.9500
C18A—H18A	0.9500	C18B—H18B	0.9500
C4A—N4A—C10A	120.24 (9)	C4B—N4B—C10B	120.25 (9)
C4A—N4A—C11A	119.61 (9)	C4B—N4B—C11B	120.48 (9)
C10A—N4A—C11A	118.30 (9)	C10B—N4B—C11B	118.66 (9)
C12A—C1A—C3A	123.21 (9)	C12B—C1B—C3B	122.32 (9)
C12A—C1A—C2A	120.85 (9)	C12B—C1B—C2B	121.55 (9)
C3A—C1A—C2A	115.94 (8)	C3B—C1B—C2B	116.09 (8)
N2A—C2A—C1A	178.90 (11)	N2B—C2B—C1B	179.17 (11)
N3A—C3A—C1A	178.58 (10)	N3B—C3B—C1B	179.14 (10)
N4A—C4A—C5A	121.52 (9)	N4B—C4B—C5B	121.31 (9)
N4A—C4A—C9A	121.08 (9)	N4B—C4B—C9B	121.38 (9)
C5A—C4A—C9A	117.39 (8)	C5B—C4B—C9B	117.31 (9)
C6A—C5A—C4A	120.55 (9)	C6B—C5B—C4B	120.72 (9)
C6A—C5A—H5A	119.7	C6B—C5B—H5B	119.6
C4A—C5A—H5A	119.7	C4B—C5B—H5B	119.6
C5A—C6A—C7A	122.44 (9)	C5B—C6B—C7B	122.29 (9)
C5A—C6A—H6A	118.8	C5B—C6B—H6B	118.9
C7A—C6A—H6A	118.8	C7B—C6B—H6B	118.9
C8A—C7A—C6A	116.71 (8)	C6B—C7B—C8B	116.67 (9)
C8A—C7A—C18A	123.79 (8)	C6B—C7B—C18B	119.39 (9)
C6A—C7A—C18A	119.50 (8)	C8B—C7B—C18B	123.91 (9)
C9A—C8A—C7A	121.78 (9)	C9B—C8B—C7B	122.01 (9)
C9A—C8A—H8A	119.1	C9B—C8B—H8B	119.0
C7A—C8A—H8A	119.1	C7B—C8B—H8B	119.0
C8A—C9A—C4A	121.14 (9)	C8B—C9B—C4B	121.00 (9)
C8A—C9A—H9A	119.4	C8B—C9B—H9B	119.5
C4A—C9A—H9A	119.4	C4B—C9B—H9B	119.5
N4A—C10A—H10D	109.5	N4B—C10B—H10A	109.5
N4A—C10A—H10E	109.5	N4B—C10B—H10B	109.5
H10D—C10A—H10E	109.5	H10A—C10B—H10B	109.5
N4A—C10A—H10F	109.5	N4B—C10B—H10C	109.5
H10D—C10A—H10F	109.5	H10A—C10B—H10C	109.5
H10E—C10A—H10F	109.5	H10B—C10B—H10C	109.5
N4A—C11A—H11D	109.5	N4B—C11B—H11A	109.5
N4A—C11A—H11E	109.5	N4B—C11B—H11B	109.5
H11D—C11A—H11E	109.5	H11A—C11B—H11B	109.5
N4A—C11A—H11F	109.5	N4B—C11B—H11C	109.5
H11D—C11A—H11F	109.5	H11A—C11B—H11C	109.5
H11E—C11A—H11F	109.5	H11B—C11B—H11C	109.5
C1A—C12A—C13A	126.47 (9)	C1B—C12B—C13B	125.31 (9)
C1A—C12A—H12A	116.8	C1B—C12B—H12B	117.3
C13A—C12A—H12A	116.8	C13B—C12B—H12B	117.3
C14A—C13A—C12A	119.65 (9)	C14B—C13B—C12B	120.74 (9)
C14A—C13A—H13A	120.2	C14B—C13B—H13B	119.6
C12A—C13A—H13A	120.2	C12B—C13B—H13B	119.6
C13A—C14A—C15A	125.96 (9)	C13B—C14B—C15B	124.70 (9)
C13A—C14A—H14A	117.0	C13B—C14B—H14B	117.6
C15A—C14A—H14A	117.0	C15B—C14B—H14B	117.6
C16A—C15A—C14A	121.52 (9)	C16B—C15B—C14B	122.49 (9)
C16A—C15A—H15A	119.2	C16B—C15B—H15B	118.8
C14A—C15A—H15A	119.2	C14B—C15B—H15B	118.8
C15A—C16A—C17A	125.53 (9)	C15B—C16B—C17B	125.46 (9)
C15A—C16A—H16A	117.2	C15B—C16B—H16B	117.3
C17A—C16A—H16A	117.2	C17B—C16B—H16B	117.3
C18A—C17A—C16A	122.11 (9)	C18B—C17B—C16B	122.03 (9)
C18A—C17A—H17A	118.9	C18B—C17B—H17B	119.0
C16A—C17A—H17A	118.9	C16B—C17B—H17B	119.0
C17A—C18A—C7A	127.81 (9)	C17B—C18B—C7B	128.03 (9)
C17A—C18A—H18A	116.1	C17B—C18B—H18B	116.0
C7A—C18A—H18A	116.1	C7B—C18B—H18B	116.0
C10A—N4A—C4A—C5A	5.39 (15)	C10B—N4B—C4B—C5B	−9.73 (15)
C11A—N4A—C4A—C5A	169.65 (9)	C11B—N4B—C4B—C5B	179.36 (10)
C10A—N4A—C4A—C9A	−175.46 (9)	C10B—N4B—C4B—C9B	170.44 (10)
C11A—N4A—C4A—C9A	−11.20 (15)	C11B—N4B—C4B—C9B	−0.47 (15)
N4A—C4A—C5A—C6A	178.91 (9)	N4B—C4B—C5B—C6B	179.97 (9)
C9A—C4A—C5A—C6A	−0.28 (14)	C9B—C4B—C5B—C6B	−0.19 (14)
C4A—C5A—C6A—C7A	0.00 (14)	C4B—C5B—C6B—C7B	−0.35 (15)
C5A—C6A—C7A—C8A	−0.08 (14)	C5B—C6B—C7B—C8B	0.53 (14)
C5A—C6A—C7A—C18A	179.01 (9)	C5B—C6B—C7B—C18B	−177.57 (9)
C6A—C7A—C8A—C9A	0.46 (14)	C6B—C7B—C8B—C9B	−0.16 (14)
C18A—C7A—C8A—C9A	−178.59 (9)	C18B—C7B—C8B—C9B	177.84 (9)
C7A—C8A—C9A—C4A	−0.77 (15)	C7B—C8B—C9B—C4B	−0.38 (15)
N4A—C4A—C9A—C8A	−178.53 (9)	N4B—C4B—C9B—C8B	−179.62 (9)
C5A—C4A—C9A—C8A	0.66 (14)	C5B—C4B—C9B—C8B	0.55 (14)
C3A—C1A—C12A—C13A	1.60 (15)	C3B—C1B—C12B—C13B	4.19 (15)
C2A—C1A—C12A—C13A	−178.12 (9)	C2B—C1B—C12B—C13B	−178.19 (9)
C1A—C12A—C13A—C14A	−179.71 (9)	C1B—C12B—C13B—C14B	−175.83 (9)
C12A—C13A—C14A—C15A	179.02 (9)	C12B—C13B—C14B—C15B	−176.96 (9)
C13A—C14A—C15A—C16A	−178.61 (9)	C13B—C14B—C15B—C16B	−172.94 (10)
C14A—C15A—C16A—C17A	179.10 (9)	C14B—C15B—C16B—C17B	−177.55 (9)
C15A—C16A—C17A—C18A	178.97 (9)	C15B—C16B—C17B—C18B	−175.53 (10)
C16A—C17A—C18A—C7A	179.02 (9)	C16B—C17B—C18B—C7B	−175.60 (9)
C8A—C7A—C18A—C17A	−5.31 (16)	C6B—C7B—C18B—C17B	−173.07 (10)
C6A—C7A—C18A—C17A	175.67 (9)	C8B—C7B—C18B—C17B	8.98 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11A—H11D···N3A^i	0.98	2.63	3.5479 (15)	157
C11A—H11E···N2B^ii	0.98	2.54	3.4880 (14)	164

Symmetry codes: (i) −x, −y, −z; (ii) −x+1, y−1/2, −z+3/2.