2-(4-Amino­phen­yl)-3-[3,4-bis­(pyridin-2-ylmeth­oxy)phen­yl]acrylo­nitrile

Liu, G.; Liu, Q.; Zhang, H.; Yu, J.

doi:10.1107/S2414314618013299

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 9| September 2018| x181329

https://doi.org/10.1107/S2414314618013299

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2-(4-Aminophenyl)-3-[3,4-bis(pyridin-2-ylmethoxy)phenyl]acrylonitrile

Gang Liu,^a Qingsong Liu,^a Huihui Zhang ^a and Jianhua Yu ^b ^*

^aDepartment of Chemistry, Anhui University, Hefei 230601, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Anhui University and Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials, Hefei 230601, People's Republic of China
^*Correspondence e-mail: iu_jh@163.com

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 13 August 2018; accepted 18 September 2018; online 21 September 2018)

The crystal structure of C₂₇H₂₂N₄O₂ is characterized by N—H⋯N hydrogen bonds, which connect the molecules into zigzag chains running along the b-axis direction. The central ring subtends dihedral angles of 17.89 (6)° with the aminophenyl ring and of 8.75 (9) and 28.77 (7)° with the two pyridyl rings.

Keywords: crystal structure; N—H⋯N hydrogen bonds; one-dimensional chain structure.

CCDC reference: 1576945

Structure description

A D–π–A structure formed from aniline and benzenenacrylonitrile has excellent luminescence properties (Zhang et al., 2018 ). We report here the crystal structure of 2-(4-aminophenyl)-3-[3,4-bis(pyridin-2-ylmethoxy)phenyl]acrylonitrile (Fig. 1). The central ring subtends dihedral angles of 17.89 (6)° with the aminophenyl ring and 28.77 (7) and 8.75 (9)° with the N1- and N2-containing pyridyl rings.

Figure 1
The structure of title molecule, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

In the crystal, the molecules are connected by N—H⋯N hydrogen bonds, forming zigzag chains running along the b-axis direction (Table 1, Fig. 2). Weak C—H⋯O interactions are also observed.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4B⋯N1ⁱ	0.95 (2)	2.35 (2)	3.293 (3)	172.8 (18)
N4—H4A⋯N3ⁱ	0.89 (2)	2.52 (2)	3.390 (3)	165.5 (19)
C6—H6⋯N3	0.93	2.59	3.431 (2)	151
C26—H26⋯N2ⁱⁱ	0.93	2.65	3.339 (3)	131
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+2, -y+1, -z+2.

Figure 2
Hydrogen bonds in the crystal packing of the title compound. N—H⋯N hydrogen bonds are drawn with dashed lines.

Synthesis and crystallization

To a solution of 3,4-dihydroxy-benzaldehyde (1.38 g, 10 mmol) in acetonitrile (50 ml) was added potassium carbonate (1.38 g, 10 mmol) and 2-bromomethyl-pyridine (3.44 g, 20 mmol). After the reaction mixture had been refluxed for 6 h, all the volatile components had completely evaporated and the residue was partitioned between dichloromethane and water. The organic phase was washed with water, then dried over calcium chloride, and concentrated in vacuo. The crude solid was recrystallized from petroleum ether–ethyl acetate (v/v= 1:1) solution to give a white solid. The white solid (0.5 g, 3.8 mmol) and (4-aminophenyl)acetonitrile (0.21 g, 3.8 mmol) were added to ethyl alcohol. The mixture solution was refluxed for 8 h, and the resulting yellow residue was collected by filtration and then purified by silica gel column chromatography (petroleum ether: ethyl acetate = 2:1, v/v) to afford the title compound (0.29 g, 43%). Yellow single crystals were obtained by slow evaporation from acetonitrile solution.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₇H₂₂N₄O₂
M_r	434.49
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.0233 (15), 16.877 (3), 17.013 (3)
β (°)	101.021 (2)
V (Å³)	2261.2 (7)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.21 × 0.19

Data collection
Diffractometer	Bruker SMART CCD area detector
No. of measured, independent and observed [I > 2σ(I)] reflections	16528, 4222, 3016
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.116, 1.07
No. of reflections	4222
No. of parameters	306
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.12
Computer programs: SMART and SAINT (Bruker, 2000 ) and SHELXS, SHELXL and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1576945

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314618013299/bt4071sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618013299/bt4071Isup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314618013299/bt4071Isup3.cml

checkCIF report

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

2-(4-Aminophenyl)-3-[3,4-bis(pyridin-2-ylmethoxy)phenyl]acrylonitrile top

Crystal data top

C₂₇H₂₂N₄O₂	F(000) = 912
M_r = 434.49	D_x = 1.276 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.0233 (15) Å	Cell parameters from 4649 reflections
b = 16.877 (3) Å	θ = 2.4–24.8°
c = 17.013 (3) Å	µ = 0.08 mm⁻¹
β = 101.021 (2)°	T = 296 K
V = 2261.2 (7) Å³	Block, yellow
Z = 4	0.21 × 0.20 × 0.19 mm

Data collection top

Bruker SMART CCD area detector diffractometer	3016 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.025
Graphite monochromator	θ_max = 25.5°, θ_min = 1.7°
phi and ω scans	h = −9→9
16528 measured reflections	k = −20→20
4222 independent reflections	l = −20→20

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.116	w = 1/[σ²(F_o²) + (0.0544P)² + 0.1757P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
4222 reflections	Δρ_max = 0.13 e Å⁻³
306 parameters	Δρ_min = −0.12 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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.

All H-atom positions were taken from a Fourier map. The H atoms were refined using a riding model with U_iso(H) = 1.2U_eq(C,N).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.49999 (13)	0.35393 (6)	0.60726 (6)	0.0624 (3)
O2	0.64442 (13)	0.43936 (6)	0.72240 (6)	0.0640 (3)
N1	0.5073 (2)	0.18016 (8)	0.49938 (9)	0.0793 (4)
N2	0.9308 (2)	0.45055 (9)	0.90889 (9)	0.0839 (5)
N3	0.08360 (19)	0.41255 (8)	0.36157 (8)	0.0721 (4)
N4	−0.3243 (2)	0.75632 (11)	0.17390 (10)	0.0807 (5)
H4B	−0.383 (3)	0.7318 (13)	0.1266 (14)	0.114 (8)*
H4A	−0.276 (3)	0.8029 (14)	0.1678 (13)	0.115 (8)*
C1	0.44974 (17)	0.43157 (8)	0.60235 (8)	0.0484 (3)
C2	0.53138 (17)	0.47891 (8)	0.66594 (8)	0.0502 (3)
C3	0.49239 (19)	0.55817 (9)	0.66679 (9)	0.0560 (4)
H3	0.545197	0.590099	0.708799	0.067*
C4	0.37400 (19)	0.59051 (9)	0.60481 (8)	0.0555 (4)
H4	0.349164	0.644269	0.605985	0.067*
C5	0.29154 (17)	0.54486 (8)	0.54107 (8)	0.0484 (3)
C6	0.33223 (17)	0.46381 (8)	0.54156 (8)	0.0501 (4)
H6	0.278638	0.431542	0.500006	0.060*
C11	0.4137 (2)	0.30045 (9)	0.55064 (9)	0.0644 (4)
H11A	0.415632	0.318992	0.496858	0.077*
H11B	0.296336	0.295468	0.556604	0.077*
C12	0.50242 (19)	0.22186 (9)	0.56499 (9)	0.0592 (4)
C13	0.5746 (3)	0.19608 (10)	0.64029 (11)	0.0829 (6)
H13	0.564635	0.226012	0.685047	0.099*
C14	0.6619 (3)	0.12559 (12)	0.64889 (13)	0.0966 (7)
H14	0.713511	0.107670	0.699380	0.116*
C15	0.6716 (3)	0.08249 (12)	0.58249 (15)	0.1040 (7)
H15	0.731751	0.035105	0.586148	0.125*
C16	0.5897 (3)	0.11113 (13)	0.50989 (14)	0.1060 (7)
H16	0.591819	0.080287	0.464790	0.127*
C21	0.7269 (2)	0.47956 (9)	0.79186 (9)	0.0609 (4)
H21A	0.643897	0.504435	0.818532	0.073*
H21B	0.801109	0.520361	0.777763	0.073*
C22	0.82829 (19)	0.41938 (9)	0.84601 (8)	0.0566 (4)
C23	0.8152 (2)	0.33945 (10)	0.83217 (10)	0.0700 (5)
H23	0.742020	0.319653	0.787431	0.084*
C24	0.9128 (3)	0.28889 (11)	0.88595 (12)	0.0837 (5)
H24	0.908267	0.234429	0.877454	0.100*
C25	1.0158 (3)	0.31990 (13)	0.95159 (12)	0.0909 (6)
H25	1.080498	0.287013	0.989461	0.109*
C26	1.0221 (3)	0.39952 (14)	0.96067 (12)	0.1004 (7)
H26	1.093962	0.420198	1.005379	0.120*
C31	0.17363 (17)	0.58435 (8)	0.47739 (8)	0.0517 (4)
H31	0.157669	0.637714	0.487389	0.062*
C32	0.08303 (17)	0.55909 (8)	0.40689 (8)	0.0482 (3)
C33	0.08525 (18)	0.47669 (9)	0.38329 (9)	0.0537 (4)
C34	−0.02236 (17)	0.61078 (8)	0.34649 (8)	0.0491 (3)
C35	−0.0004 (2)	0.69284 (9)	0.34669 (9)	0.0625 (4)
H35	0.082626	0.715972	0.385550	0.075*
C36	−0.0996 (2)	0.74018 (9)	0.29030 (10)	0.0697 (5)
H36	−0.083483	0.794767	0.292461	0.084*
C37	−0.2235 (2)	0.70805 (9)	0.23018 (9)	0.0601 (4)
C38	−0.24557 (19)	0.62686 (9)	0.22986 (9)	0.0609 (4)
H38	−0.328422	0.603694	0.190933	0.073*
C39	−0.14660 (19)	0.57983 (9)	0.28634 (9)	0.0565 (4)
H39	−0.163616	0.525305	0.284117	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0689 (7)	0.0464 (6)	0.0622 (6)	0.0023 (5)	−0.0119 (5)	−0.0040 (5)
O2	0.0697 (7)	0.0587 (6)	0.0540 (6)	0.0053 (5)	−0.0127 (5)	−0.0048 (5)
N1	0.0970 (11)	0.0676 (9)	0.0737 (9)	0.0127 (8)	0.0175 (8)	−0.0085 (8)
N2	0.0964 (11)	0.0797 (10)	0.0616 (9)	0.0045 (8)	−0.0206 (8)	−0.0027 (7)
N3	0.0823 (10)	0.0548 (8)	0.0724 (9)	0.0021 (7)	−0.0020 (7)	−0.0032 (7)
N4	0.0973 (12)	0.0680 (10)	0.0690 (10)	0.0147 (9)	−0.0039 (9)	0.0166 (8)
C1	0.0481 (8)	0.0462 (8)	0.0500 (8)	−0.0017 (6)	0.0071 (6)	0.0014 (6)
C2	0.0483 (8)	0.0537 (9)	0.0462 (8)	−0.0004 (7)	0.0033 (6)	0.0021 (6)
C3	0.0580 (9)	0.0552 (9)	0.0515 (8)	−0.0027 (7)	0.0020 (7)	−0.0073 (7)
C4	0.0599 (9)	0.0491 (8)	0.0564 (9)	0.0032 (7)	0.0086 (7)	−0.0023 (7)
C5	0.0466 (8)	0.0514 (8)	0.0475 (8)	−0.0001 (6)	0.0101 (6)	0.0023 (6)
C6	0.0502 (8)	0.0508 (8)	0.0469 (8)	−0.0024 (6)	0.0031 (7)	−0.0013 (6)
C11	0.0672 (10)	0.0542 (9)	0.0643 (10)	−0.0010 (8)	−0.0063 (8)	−0.0083 (7)
C12	0.0614 (10)	0.0494 (9)	0.0646 (10)	−0.0062 (7)	0.0063 (8)	−0.0049 (7)
C13	0.1142 (16)	0.0580 (11)	0.0711 (12)	0.0086 (10)	0.0041 (11)	0.0004 (8)
C14	0.1231 (18)	0.0708 (13)	0.0920 (15)	0.0152 (12)	0.0106 (13)	0.0205 (11)
C15	0.1274 (19)	0.0717 (13)	0.1205 (19)	0.0357 (13)	0.0428 (16)	0.0181 (13)
C16	0.144 (2)	0.0806 (14)	0.0999 (16)	0.0316 (14)	0.0405 (15)	−0.0108 (12)
C21	0.0706 (10)	0.0601 (9)	0.0474 (8)	0.0004 (8)	−0.0008 (7)	−0.0050 (7)
C22	0.0592 (9)	0.0615 (9)	0.0468 (8)	0.0004 (7)	0.0044 (7)	0.0006 (7)
C23	0.0766 (11)	0.0638 (11)	0.0662 (10)	0.0003 (8)	0.0051 (9)	0.0025 (8)
C24	0.0921 (14)	0.0663 (11)	0.0924 (14)	0.0089 (10)	0.0166 (11)	0.0132 (10)
C25	0.0896 (14)	0.0964 (16)	0.0806 (13)	0.0255 (12)	0.0008 (11)	0.0244 (12)
C26	0.1075 (17)	0.1034 (17)	0.0730 (13)	0.0144 (13)	−0.0259 (11)	0.0026 (12)
C31	0.0526 (9)	0.0480 (8)	0.0542 (9)	0.0032 (6)	0.0098 (7)	0.0021 (7)
C32	0.0468 (8)	0.0485 (8)	0.0499 (8)	0.0014 (6)	0.0111 (6)	0.0042 (6)
C33	0.0517 (9)	0.0554 (9)	0.0511 (8)	0.0011 (7)	0.0025 (7)	0.0063 (7)
C34	0.0495 (8)	0.0502 (8)	0.0482 (8)	0.0012 (6)	0.0112 (7)	0.0051 (6)
C35	0.0755 (11)	0.0532 (9)	0.0546 (9)	−0.0027 (8)	0.0021 (8)	0.0021 (7)
C36	0.0951 (13)	0.0473 (9)	0.0635 (10)	0.0031 (8)	0.0073 (9)	0.0056 (7)
C37	0.0675 (10)	0.0580 (9)	0.0541 (9)	0.0096 (8)	0.0097 (8)	0.0102 (7)
C38	0.0578 (9)	0.0624 (10)	0.0585 (9)	−0.0032 (8)	0.0006 (7)	0.0073 (7)
C39	0.0579 (9)	0.0493 (8)	0.0601 (9)	−0.0031 (7)	0.0059 (7)	0.0078 (7)

Geometric parameters (Å, º) top

O1—C1	1.3688 (16)	C14—H14	0.9300
O1—C11	1.4023 (17)	C15—C16	1.371 (3)
O2—C2	1.3630 (16)	C15—H15	0.9300
O2—C21	1.4128 (17)	C16—H16	0.9300
N1—C12	1.3264 (19)	C21—C22	1.502 (2)
N1—C16	1.335 (2)	C21—H21A	0.9700
N2—C22	1.3271 (19)	C21—H21B	0.9700
N2—C26	1.345 (2)	C22—C23	1.370 (2)
N3—C33	1.1431 (18)	C23—C24	1.380 (2)
N4—C37	1.392 (2)	C23—H23	0.9300
N4—H4B	0.95 (2)	C24—C25	1.360 (3)
N4—H4A	0.89 (2)	C24—H24	0.9300
C1—C6	1.3718 (18)	C25—C26	1.352 (3)
C1—C2	1.4025 (19)	C25—H25	0.9300
C2—C3	1.374 (2)	C26—H26	0.9300
C3—C4	1.389 (2)	C31—C32	1.3473 (19)
C3—H3	0.9300	C31—H31	0.9300
C4—C5	1.3903 (19)	C32—C33	1.448 (2)
C4—H4	0.9300	C32—C34	1.4831 (18)
C5—C6	1.4060 (19)	C34—C39	1.3870 (19)
C5—C31	1.4564 (19)	C34—C35	1.396 (2)
C6—H6	0.9300	C35—C36	1.379 (2)
C11—C12	1.503 (2)	C35—H35	0.9300
C11—H11A	0.9700	C36—C37	1.393 (2)
C11—H11B	0.9700	C36—H36	0.9300
C12—C13	1.372 (2)	C37—C38	1.382 (2)
C13—C14	1.374 (3)	C38—C39	1.376 (2)
C13—H13	0.9300	C38—H38	0.9300
C14—C15	1.358 (3)	C39—H39	0.9300

C1—O1—C11	118.25 (11)	O2—C21—C22	107.48 (12)
C2—O2—C21	119.76 (11)	O2—C21—H21A	110.2
C12—N1—C16	116.36 (16)	C22—C21—H21A	110.2
C22—N2—C26	116.77 (17)	O2—C21—H21B	110.2
C37—N4—H4B	117.3 (13)	C22—C21—H21B	110.2
C37—N4—H4A	112.7 (15)	H21A—C21—H21B	108.5
H4B—N4—H4A	116.4 (19)	N2—C22—C23	122.97 (15)
O1—C1—C6	125.29 (12)	N2—C22—C21	113.95 (14)
O1—C1—C2	114.18 (12)	C23—C22—C21	123.08 (14)
C6—C1—C2	120.53 (13)	C22—C23—C24	118.67 (17)
O2—C2—C3	126.26 (13)	C22—C23—H23	120.7
O2—C2—C1	114.47 (12)	C24—C23—H23	120.7
C3—C2—C1	119.27 (13)	C25—C24—C23	119.00 (18)
C2—C3—C4	119.90 (13)	C25—C24—H24	120.5
C2—C3—H3	120.1	C23—C24—H24	120.5
C4—C3—H3	120.1	C26—C25—C24	118.67 (18)
C3—C4—C5	121.93 (14)	C26—C25—H25	120.7
C3—C4—H4	119.0	C24—C25—H25	120.7
C5—C4—H4	119.0	N2—C26—C25	123.89 (19)
C4—C5—C6	117.33 (13)	N2—C26—H26	118.1
C4—C5—C31	118.12 (13)	C25—C26—H26	118.1
C6—C5—C31	124.52 (13)	C32—C31—C5	132.90 (14)
C1—C6—C5	121.04 (13)	C32—C31—H31	113.6
C1—C6—H6	119.5	C5—C31—H31	113.6
C5—C6—H6	119.5	C31—C32—C33	121.16 (13)
O1—C11—C12	107.47 (12)	C31—C32—C34	124.73 (13)
O1—C11—H11A	110.2	C33—C32—C34	114.10 (12)
C12—C11—H11A	110.2	N3—C33—C32	177.17 (16)
O1—C11—H11B	110.2	C39—C34—C35	116.61 (13)
C12—C11—H11B	110.2	C39—C34—C32	121.59 (13)
H11A—C11—H11B	108.5	C35—C34—C32	121.80 (13)
N1—C12—C13	122.85 (15)	C36—C35—C34	121.17 (15)
N1—C12—C11	114.88 (14)	C36—C35—H35	119.4
C13—C12—C11	122.27 (15)	C34—C35—H35	119.4
C12—C13—C14	119.32 (18)	C35—C36—C37	121.43 (15)
C12—C13—H13	120.3	C35—C36—H36	119.3
C14—C13—H13	120.3	C37—C36—H36	119.3
C15—C14—C13	118.96 (19)	C38—C37—N4	121.36 (16)
C15—C14—H14	120.5	C38—C37—C36	117.52 (14)
C13—C14—H14	120.5	N4—C37—C36	121.09 (16)
C14—C15—C16	117.81 (19)	C39—C38—C37	120.87 (14)
C14—C15—H15	121.1	C39—C38—H38	119.6
C16—C15—H15	121.1	C37—C38—H38	119.6
N1—C16—C15	124.6 (2)	C38—C39—C34	122.39 (14)
N1—C16—H16	117.7	C38—C39—H39	118.8
C15—C16—H16	117.7	C34—C39—H39	118.8

C11—O1—C1—C6	−6.9 (2)	C26—N2—C22—C23	−1.0 (3)
C11—O1—C1—C2	173.89 (13)	C26—N2—C22—C21	178.49 (17)
C21—O2—C2—C3	3.6 (2)	O2—C21—C22—N2	171.32 (14)
C21—O2—C2—C1	−176.08 (13)	O2—C21—C22—C23	−9.2 (2)
O1—C1—C2—O2	−1.09 (18)	N2—C22—C23—C24	0.0 (3)
C6—C1—C2—O2	179.70 (12)	C21—C22—C23—C24	−179.40 (16)
O1—C1—C2—C3	179.23 (13)	C22—C23—C24—C25	1.4 (3)
C6—C1—C2—C3	0.0 (2)	C23—C24—C25—C26	−1.7 (3)
O2—C2—C3—C4	179.98 (14)	C22—N2—C26—C25	0.6 (3)
C1—C2—C3—C4	−0.4 (2)	C24—C25—C26—N2	0.8 (4)
C2—C3—C4—C5	0.3 (2)	C4—C5—C31—C32	175.56 (15)
C3—C4—C5—C6	0.1 (2)	C6—C5—C31—C32	−2.4 (3)
C3—C4—C5—C31	−177.94 (13)	C5—C31—C32—C33	3.3 (2)
O1—C1—C6—C5	−178.68 (13)	C5—C31—C32—C34	−175.23 (14)
C2—C1—C6—C5	0.4 (2)	C31—C32—C34—C39	−162.29 (14)
C4—C5—C6—C1	−0.5 (2)	C33—C32—C34—C39	19.11 (19)
C31—C5—C6—C1	177.43 (13)	C31—C32—C34—C35	18.4 (2)
C1—O1—C11—C12	175.28 (12)	C33—C32—C34—C35	−160.15 (14)
C16—N1—C12—C13	−1.1 (3)	C39—C34—C35—C36	0.9 (2)
C16—N1—C12—C11	178.01 (17)	C32—C34—C35—C36	−179.82 (14)
O1—C11—C12—N1	−144.35 (15)	C34—C35—C36—C37	−1.1 (3)
O1—C11—C12—C13	34.8 (2)	C35—C36—C37—C38	1.1 (2)
N1—C12—C13—C14	2.6 (3)	C35—C36—C37—N4	179.39 (16)
C11—C12—C13—C14	−176.45 (18)	N4—C37—C38—C39	−179.21 (15)
C12—C13—C14—C15	−1.2 (3)	C36—C37—C38—C39	−0.9 (2)
C13—C14—C15—C16	−1.4 (4)	C37—C38—C39—C34	0.8 (2)
C12—N1—C16—C15	−1.8 (3)	C35—C34—C39—C38	−0.7 (2)
C14—C15—C16—N1	3.1 (4)	C32—C34—C39—C38	179.97 (13)
C2—O2—C21—C22	174.24 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···N1ⁱ	0.95 (2)	2.35 (2)	3.293 (3)	172.8 (18)
N4—H4A···N3ⁱ	0.89 (2)	2.52 (2)	3.390 (3)	165.5 (19)
C6—H6···N3	0.93	2.59	3.431 (2)	151
C26—H26···N2ⁱⁱ	0.93	2.65	3.339 (3)	131

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

Acknowledgements

This work was supported by the Undergraduate Research Training Program of Anhui University (KYXL2017019).

Funding information

Funding for this research was provided by: Anhui University (award No. KYXL2017019).

References

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