Crystal structure of 1,2-bis­(2,6-di­methyl­phen­yl)-3-phenyl­guanidine

Han, H.; Guo, Z.; Wei, X.

doi:10.1107/S2056989015011822

organic compounds

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ISSN: 2056-9890

Volume 71| Part 7| July 2015| Pages o506-o507

doi:10.1107/S2056989015011822

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Crystal structure of 1,2-bis(2,6-dimethylphenyl)-3-phenylguanidine

Hongfei Han,^a ^* Zhiqiang Guo ^b and Xuehong Wei ^a

^aThe School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, People's Republic of China, and ^bInstitute of Applied Chemistry, Shanxi University, Taiyuan, Shanxi 030006, People's Republic of China
^*Correspondence e-mail: hfhan001@163.com

Edited by S. Parkin, University of Kentucky, USA (Received 13 June 2015; accepted 20 June 2015; online 27 June 2015)

In the title compound, C₂₃H₂₅N₃, the dihedral angles between the planes of the benzene ring and the two substituent dimethylphenyl rings are 60.94 (7)° and 88.08 (7)°, and the dihedral angle between the planes of the two dimethylphenyl rings is 58.01 (7)°. In the crystal, weak C—H⋯N interactions exist between adjacent molecules. One of the dimethylphenyl rings has a small amount of π–π overlap with the phenyl ring of an adjacent molecule [centroid-to-centroid distance = 3.9631 (12) Å].

Keywords: crystal structure; guanidines; hydrogen bonding; π–π overlap.

CCDC reference: 1407910

1. Related literature

For similar structures of various related compounds, see: Boeré et al. (2000 ); Brazeau et al. (2012 ); Ghosh et al. (2008 ); Han & Huynh (2009 ); Chlupatý & Padělková (2014 ); Yildirim et al. (2007 ); Zhang et al. (2009 ). For applications of guanidines, see: Berlinck (2002 ); Heys et al. (2000 ); Laeckmann et al. (2002 ); Kelley et al. (2001 ); Moroni et al. (2001 ).

2. Experimental

2.1. Crystal data

C₂₃H₂₅N₃
M_r = 343.46
Orthorhombic, P c a 2₁
a = 19.003 (7) Å
b = 7.924 (3) Å
c = 13.056 (5) Å
V = 1966.0 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 194 K
0.35 × 0.33 × 0.30 mm

2.2. Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.976, T_max = 0.980
10737 measured reflections
3547 independent reflections
2649 reflections with I > 2σ(I)
R_int = 0.038

2.3. Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.104
S = 1.02
3547 reflections
239 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯N2ⁱ	0.95	2.61	3.457 (3)	148
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+2, z]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1407910

Crystal structure: contains datablock I. DOI: 10.1107/S2056989015011822/pk2556sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015011822/pk2556Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015011822/pk2556Isup3.cml

checkCIF report

Structural commentary top

Guanidines are important compounds due to their possible application in medicine, biology and chemistry (Berlinck et al., 2002; Heys et al., 2000). In particular, they have received increasing interest as medicinal agents with antitumour, anti-hypertensive, antiglaucoma and cardiotonic activities (Laeckmann et al., 2002; Kelley et al., 2001; Moroni et al., 2001). In search of guanidinato metal complexes and their catalytic behaviors, we synthesized a new substituted guanidine by insertion of phenylamine with a symmetric carbodiimine, the crystal structure of which is presented here. In addition to two examples of phenyl-substituted benzimidazol amines (Ghosh et al., 2008; Yildirim et al., 2007), the title compound is structurally similar to the known compounds, 1-cyclohexyl-2,3-diphenylguanidine (Zhang et al., 2009), 1-(2,6-diisopropylphenyl)-2,3-dimesitylguanidine (Brazeau et al., 2012), N,N',N''-tris(2,6-dimethylphenyl)guanidine (Han & Huynh, 2009), 2-[2,6-Bis(propan-2-yl)phenyl]-1,3-dicyclohexylguanidine (Chlupatý & Padělková, 2014) and N,N',N''-tris(2,6-di-isopropylphenyl)guanidine (Boere et al., 2000).

The molecular structure of the title compound is illustrated in Fig. 1. The C9—N2 bond in the guanidine unit is 1.266 (2) Å, and is characteristic for a C═N imine double bond. The bond lengths of C9—N1 and C9—N3 are 1.365 (2) and 1.376 (2) Å, showing single bond character (Allen et al., 1987). The N—C9—N angles are 124.15 (18)° (N1—C9—N2), 121.58 (17)° (N2—C9—N3) and 114.26 (17)° (N1—C9—N3), indicating a deviation of the CN₃ plane from an ideal trigonal planar geometry. The dihedral angles between the planes of the benzene ring and the two substituent dimethylphenyl rings are 60.94 (7) and 88.08 (7)°, and the dihedral angle between the planes of the two dimethylphenyl rings is 58.01 (7)°. In the crystal, in addition to van der Waals interactions, weak C—H···N and N—H···C interactions exist between adjacent molecules. One of the dimethylphenyl rings has a small amount of π···π overlap with the phenyl ring of an adjacent (1-x, 2-y, 0.5+z) molecule [centroid-to-centroid distance = 3.9631 (12) Å].

Synthesis and crystallization top

To a stirred solution of phenylamine (1.863 g, 20 mmol) in hexane was added N,N'-dimethylphenyl carbodiimine (5.007 g, 20 mmol), followed by the addition of the trimethylaluminum (2.5 M, 0.40 mL, 1 mmol). After stirring for 2 h, the white precipitate was collected by suction filtration and recrystallized from hexane-diethylether (1:1) solution to obtain colorless crystals of 1,2-bis(2,6-dimethylphenyl)-3-phenylguanidine (yield: 90%). Anal. Calc. for C₂₃H₂₅N₃: C, 80.43; H, 7.34; N, 12.23. Found: C, 80.32; H, 7.25; N, 12.31%. ¹H NMR (300 MHz, CDCl₃, 25 °C) δ p.p.m. 2.35 (d, 12H, CH₃), 5.06 (s, 1H, NH), 5.56 (s, 1H, NH), 6.91 (s, 2H, PhH), 7.00 (s, 2H, PhH), 7.14 (s, 4H, PhH), 7.28 (s, 1H, PhH) , 7.58 (s, 2H, PhH).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. The N—H hydrogen atoms were located in a difference Fourier map and constrained (N—H = 0.87 Å). The C-bound H-atoms were included in calculated positions and treated as riding atoms: C—H = 0.95 - 0.98 Å with U_iso (H) = 1.2 or 1.5U_eq (C_Me).

Related literature top

For similar structures of various related compounds, see: Boeré et al. (2000); Brazeau et al. (2012); Ghosh et al. (2008); Han & Huynh (2009); Chlupatý & Padělková (2014); Yildirim et al. (2007); Zhang et al. (2009). For applications of guanidines, see: Berlinck (2002); Heys et al. (2000); Laeckmann et al. (2002); Kelley et al. (2001); Moroni et al. (2001).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.

1,2-Bis(2,6-dimethylphenyl)-3-phenylguanidine top

Crystal data top

C₂₃H₂₅N₃	F(000) = 736
M_r = 343.46	D_x = 1.160 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2316 reflections
a = 19.003 (7) Å	θ = 2.8–23.5°
b = 7.924 (3) Å	µ = 0.07 mm⁻¹
c = 13.056 (5) Å	T = 194 K
V = 1966.0 (13) Å³	Block, colourless
Z = 4	0.35 × 0.33 × 0.30 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3547 independent reflections
Radiation source: fine-focus sealed tube	2649 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→23
T_min = 0.976, T_max = 0.980	k = −9→5
10737 measured reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0564P)²] where P = (F_o² + 2F_c²)/3
3547 reflections	(Δ/σ)_max = 0.001
239 parameters	Δρ_max = 0.14 e Å⁻³
1 restraint	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₂₃H₂₅N₃	V = 1966.0 (13) Å³
M_r = 343.46	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 19.003 (7) Å	µ = 0.07 mm⁻¹
b = 7.924 (3) Å	T = 194 K
c = 13.056 (5) Å	0.35 × 0.33 × 0.30 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3547 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2649 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.980	R_int = 0.038
10737 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	1 restraint
wR(F²) = 0.104	H-atom parameters constrained
S = 1.01	Δρ_max = 0.14 e Å⁻³
3547 reflections	Δρ_min = −0.14 e Å⁻³
239 parameters

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

	x	y	z	U_iso*/U_eq
N1	0.51390 (8)	0.8726 (2)	0.22933 (14)	0.0499 (4)
H1	0.5001	0.8129	0.2815	0.060*
N2	0.39761 (8)	0.9417 (2)	0.19326 (13)	0.0470 (4)
N3	0.48706 (8)	1.0319 (2)	0.08715 (13)	0.0494 (5)
H3	0.5300	1.0109	0.0680	0.059*
C1	0.58760 (9)	0.8820 (3)	0.21187 (15)	0.0414 (5)
C2	0.62483 (11)	1.0196 (3)	0.24776 (18)	0.0535 (6)
C3	0.69708 (12)	1.0198 (4)	0.2354 (2)	0.0693 (7)
H3A	0.7238	1.1136	0.2586	0.083*
C4	0.73035 (12)	0.8867 (4)	0.1904 (2)	0.0695 (7)
H4	0.7801	0.8879	0.1840	0.083*
C5	0.69327 (12)	0.7521 (4)	0.15447 (18)	0.0612 (6)
H5	0.7173	0.6614	0.1223	0.073*
C6	0.62094 (10)	0.7464 (3)	0.16442 (17)	0.0482 (5)
C7	0.58943 (16)	1.1640 (3)	0.3014 (2)	0.0825 (8)
H7A	0.5631	1.1213	0.3605	0.124*
H7B	0.5570	1.2202	0.2539	0.124*
H7C	0.6250	1.2448	0.3247	0.124*
C8	0.57928 (15)	0.5980 (3)	0.1261 (2)	0.0732 (7)
H8A	0.5423	0.6375	0.0796	0.110*
H8B	0.5578	0.5392	0.1843	0.110*
H8C	0.6106	0.5204	0.0894	0.110*
C9	0.46259 (9)	0.9480 (3)	0.17228 (15)	0.0392 (4)
C10	0.37336 (10)	0.8594 (3)	0.28195 (16)	0.0470 (5)
C11	0.36221 (11)	0.9503 (4)	0.37126 (18)	0.0592 (7)
C12	0.32944 (14)	0.8739 (5)	0.4525 (2)	0.0830 (9)
H12	0.3214	0.9366	0.5133	0.100*
C13	0.30812 (15)	0.7093 (6)	0.4476 (3)	0.0950 (12)
H13	0.2852	0.6584	0.5044	0.114*
C14	0.32015 (14)	0.6189 (4)	0.3606 (3)	0.0918 (11)
H14	0.3059	0.5041	0.3580	0.110*
C15	0.35250 (11)	0.6897 (3)	0.2757 (2)	0.0628 (7)
C16	0.38379 (16)	1.1319 (4)	0.3781 (2)	0.0814 (9)
H16A	0.3731	1.1888	0.3133	0.122*
H16B	0.4344	1.1389	0.3916	0.122*
H16C	0.3580	1.1868	0.4338	0.122*
C17	0.36204 (16)	0.5931 (4)	0.1775 (3)	0.0942 (10)
H17A	0.3381	0.6526	0.1217	0.141*
H17B	0.3419	0.4799	0.1850	0.141*
H17C	0.4123	0.5839	0.1619	0.141*
C18	0.44829 (10)	1.1495 (3)	0.02788 (14)	0.0437 (5)
C19	0.37790 (11)	1.1326 (3)	0.00775 (16)	0.0546 (6)
H19	0.3529	1.0372	0.0326	0.065*
C20	0.34337 (13)	1.2550 (3)	−0.04892 (17)	0.0641 (7)
H20	0.2943	1.2446	−0.0611	0.077*
C21	0.37888 (15)	1.3896 (3)	−0.0873 (2)	0.0685 (7)
H21	0.3546	1.4731	−0.1258	0.082*
C22	0.44980 (15)	1.4048 (3)	−0.07045 (19)	0.0666 (7)
H22	0.4749	1.4976	−0.0985	0.080*
C23	0.48466 (11)	1.2853 (3)	−0.01269 (16)	0.0533 (5)
H23	0.5338	1.2964	−0.0007	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0348 (8)	0.0591 (10)	0.0557 (10)	0.0034 (8)	0.0009 (8)	0.0171 (9)
N2	0.0339 (9)	0.0611 (11)	0.0460 (10)	0.0061 (8)	0.0012 (7)	0.0097 (9)
N3	0.0358 (9)	0.0664 (12)	0.0461 (9)	0.0083 (8)	0.0054 (7)	0.0140 (10)
C1	0.0336 (10)	0.0483 (11)	0.0424 (11)	−0.0002 (9)	−0.0060 (8)	0.0072 (10)
C2	0.0533 (12)	0.0528 (13)	0.0543 (13)	−0.0053 (11)	−0.0068 (11)	0.0059 (11)
C3	0.0564 (14)	0.0834 (19)	0.0682 (15)	−0.0248 (14)	−0.0165 (13)	0.0080 (15)
C4	0.0356 (11)	0.111 (2)	0.0622 (15)	−0.0066 (13)	−0.0028 (11)	0.0113 (17)
C5	0.0477 (13)	0.0820 (18)	0.0540 (13)	0.0115 (12)	0.0023 (10)	−0.0007 (13)
C6	0.0432 (11)	0.0551 (13)	0.0461 (11)	0.0001 (10)	−0.0039 (10)	0.0016 (11)
C7	0.0967 (19)	0.0517 (14)	0.099 (2)	0.0000 (14)	−0.0121 (17)	−0.0118 (17)
C8	0.0800 (18)	0.0600 (17)	0.0795 (17)	−0.0056 (14)	−0.0001 (14)	−0.0135 (14)
C9	0.0368 (10)	0.0428 (11)	0.0379 (10)	0.0029 (9)	−0.0032 (9)	−0.0003 (9)
C10	0.0295 (9)	0.0615 (14)	0.0498 (12)	0.0091 (10)	0.0007 (9)	0.0086 (11)
C11	0.0449 (13)	0.0842 (18)	0.0483 (13)	0.0202 (13)	0.0008 (10)	0.0096 (13)
C12	0.0684 (18)	0.127 (3)	0.0534 (15)	0.0326 (18)	0.0107 (13)	0.0181 (18)
C13	0.0656 (17)	0.129 (3)	0.091 (2)	0.0279 (19)	0.0308 (16)	0.058 (2)
C14	0.0606 (16)	0.078 (2)	0.137 (3)	0.0074 (15)	0.0213 (18)	0.044 (2)
C15	0.0420 (12)	0.0628 (15)	0.0837 (17)	0.0046 (11)	0.0078 (12)	0.0096 (15)
C16	0.088 (2)	0.085 (2)	0.0710 (17)	0.0123 (17)	−0.0064 (15)	−0.0176 (17)
C17	0.0784 (18)	0.0710 (18)	0.133 (3)	−0.0084 (15)	0.015 (2)	−0.023 (2)
C18	0.0450 (11)	0.0506 (13)	0.0355 (10)	0.0058 (9)	0.0019 (9)	0.0008 (10)
C19	0.0453 (12)	0.0729 (17)	0.0455 (12)	0.0040 (11)	−0.0026 (9)	0.0083 (12)
C20	0.0533 (13)	0.0902 (19)	0.0487 (12)	0.0137 (13)	−0.0040 (11)	0.0067 (14)
C21	0.0819 (18)	0.0696 (18)	0.0541 (14)	0.0251 (15)	−0.0055 (13)	0.0062 (14)
C22	0.090 (2)	0.0497 (15)	0.0606 (15)	0.0046 (13)	−0.0032 (13)	0.0051 (13)
C23	0.0574 (13)	0.0517 (13)	0.0509 (12)	−0.0007 (11)	−0.0028 (11)	−0.0014 (12)

Geometric parameters (Å, º) top

N1—C9	1.365 (2)	C11—C12	1.370 (4)
N1—C1	1.421 (2)	C11—C16	1.499 (4)
N1—H1	0.8700	C12—C13	1.368 (5)
N2—C9	1.266 (2)	C12—H12	0.9500
N2—C10	1.407 (3)	C13—C14	1.363 (5)
N3—C9	1.376 (2)	C13—H13	0.9500
N3—C18	1.418 (3)	C14—C15	1.386 (4)
N3—H3	0.8699	C14—H14	0.9500
C1—C2	1.381 (3)	C15—C17	1.503 (4)
C1—C6	1.393 (3)	C16—H16A	0.9800
C2—C3	1.382 (3)	C16—H16B	0.9800
C2—C7	1.501 (4)	C16—H16C	0.9800
C3—C4	1.363 (4)	C17—H17A	0.9800
C3—H3A	0.9500	C17—H17B	0.9800
C4—C5	1.362 (3)	C17—H17C	0.9800
C4—H4	0.9500	C18—C19	1.370 (3)
C5—C6	1.381 (3)	C18—C23	1.385 (3)
C5—H5	0.9500	C19—C20	1.385 (3)
C6—C8	1.503 (3)	C19—H19	0.9500
C7—H7A	0.9800	C20—C21	1.358 (3)
C7—H7B	0.9800	C20—H20	0.9500
C7—H7C	0.9800	C21—C22	1.371 (4)
C8—H8A	0.9800	C21—H21	0.9500
C8—H8B	0.9800	C22—C23	1.380 (3)
C8—H8C	0.9800	C22—H22	0.9500
C10—C11	1.387 (3)	C23—H23	0.9500
C10—C15	1.405 (3)

C9—N1—C1	126.42 (17)	C12—C11—C16	120.2 (3)
C9—N1—H1	116.8	C10—C11—C16	120.5 (2)
C1—N1—H1	116.8	C13—C12—C11	121.3 (3)
C9—N2—C10	121.07 (16)	C13—C12—H12	119.3
C9—N3—C18	125.64 (16)	C11—C12—H12	119.3
C9—N3—H3	117.2	C14—C13—C12	119.3 (3)
C18—N3—H3	117.2	C14—C13—H13	120.3
C2—C1—C6	121.78 (17)	C12—C13—H13	120.3
C2—C1—N1	119.46 (19)	C13—C14—C15	121.9 (3)
C6—C1—N1	118.63 (17)	C13—C14—H14	119.0
C1—C2—C3	118.0 (2)	C15—C14—H14	119.0
C1—C2—C7	122.0 (2)	C14—C15—C10	117.8 (3)
C3—C2—C7	119.9 (2)	C14—C15—C17	122.0 (3)
C4—C3—C2	120.7 (2)	C10—C15—C17	120.2 (2)
C4—C3—H3A	119.7	C11—C16—H16A	109.5
C2—C3—H3A	119.7	C11—C16—H16B	109.5
C5—C4—C3	121.0 (2)	H16A—C16—H16B	109.5
C5—C4—H4	119.5	C11—C16—H16C	109.5
C3—C4—H4	119.5	H16A—C16—H16C	109.5
C4—C5—C6	120.5 (2)	H16B—C16—H16C	109.5
C4—C5—H5	119.7	C15—C17—H17A	109.5
C6—C5—H5	119.7	C15—C17—H17B	109.5
C5—C6—C1	118.0 (2)	H17A—C17—H17B	109.5
C5—C6—C8	121.2 (2)	C15—C17—H17C	109.5
C1—C6—C8	120.80 (18)	H17A—C17—H17C	109.5
C2—C7—H7A	109.5	H17B—C17—H17C	109.5
C2—C7—H7B	109.5	C19—C18—C23	119.3 (2)
H7A—C7—H7B	109.5	C19—C18—N3	123.2 (2)
C2—C7—H7C	109.5	C23—C18—N3	117.43 (18)
H7A—C7—H7C	109.5	C18—C19—C20	119.8 (2)
H7B—C7—H7C	109.5	C18—C19—H19	120.1
C6—C8—H8A	109.5	C20—C19—H19	120.1
C6—C8—H8B	109.5	C21—C20—C19	120.8 (2)
H8A—C8—H8B	109.5	C21—C20—H20	119.6
C6—C8—H8C	109.5	C19—C20—H20	119.6
H8A—C8—H8C	109.5	C20—C21—C22	119.9 (2)
H8B—C8—H8C	109.5	C20—C21—H21	120.1
N2—C9—N1	124.15 (18)	C22—C21—H21	120.1
N2—C9—N3	121.58 (17)	C21—C22—C23	120.0 (2)
N1—C9—N3	114.26 (16)	C21—C22—H22	120.0
C11—C10—C15	120.2 (2)	C23—C22—H22	120.0
C11—C10—N2	120.1 (2)	C22—C23—C18	120.2 (2)
C15—C10—N2	119.2 (2)	C22—C23—H23	119.9
C12—C11—C10	119.4 (3)	C18—C23—H23	119.9

C9—N1—C1—C2	82.9 (3)	C15—C10—C11—C12	−1.3 (3)
C9—N1—C1—C6	−101.1 (2)	N2—C10—C11—C12	170.91 (19)
C6—C1—C2—C3	0.0 (3)	C15—C10—C11—C16	−179.4 (2)
N1—C1—C2—C3	175.9 (2)	N2—C10—C11—C16	−7.3 (3)
C6—C1—C2—C7	−178.4 (2)	C10—C11—C12—C13	0.7 (4)
N1—C1—C2—C7	−2.5 (3)	C16—C11—C12—C13	178.9 (3)
C1—C2—C3—C4	−0.9 (4)	C11—C12—C13—C14	0.5 (4)
C7—C2—C3—C4	177.5 (2)	C12—C13—C14—C15	−1.0 (5)
C2—C3—C4—C5	1.4 (4)	C13—C14—C15—C10	0.4 (4)
C3—C4—C5—C6	−1.0 (4)	C13—C14—C15—C17	−176.4 (3)
C4—C5—C6—C1	0.1 (3)	C11—C10—C15—C14	0.7 (3)
C4—C5—C6—C8	−179.4 (2)	N2—C10—C15—C14	−171.5 (2)
C2—C1—C6—C5	0.4 (3)	C11—C10—C15—C17	177.6 (2)
N1—C1—C6—C5	−175.5 (2)	N2—C10—C15—C17	5.4 (3)
C2—C1—C6—C8	179.9 (2)	C9—N3—C18—C19	−37.2 (3)
N1—C1—C6—C8	4.0 (3)	C9—N3—C18—C23	144.1 (2)
C10—N2—C9—N1	2.6 (3)	C23—C18—C19—C20	−2.8 (3)
C10—N2—C9—N3	−178.32 (19)	N3—C18—C19—C20	178.5 (2)
C1—N1—C9—N2	−177.0 (2)	C18—C19—C20—C21	1.8 (3)
C1—N1—C9—N3	3.9 (3)	C19—C20—C21—C22	0.3 (4)
C18—N3—C9—N2	15.3 (3)	C20—C21—C22—C23	−1.4 (4)
C18—N3—C9—N1	−165.6 (2)	C21—C22—C23—C18	0.4 (4)
C9—N2—C10—C11	94.0 (2)	C19—C18—C23—C22	1.8 (3)
C9—N2—C10—C15	−93.7 (2)	N3—C18—C23—C22	−179.54 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N2ⁱ	0.95	2.61	3.457 (3)	148

Symmetry code: (i) x+1/2, −y+2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N2ⁱ	0.95	2.61	3.457 (3)	148

Symmetry code: (i) x+1/2, −y+2, z.

Acknowledgements

Financial support from the National Natural Science Foundation of China (No. 21272142), the Special Fund for Agro-Scientific Research in the Public Interest (No. 201303106), and the Patent Promotion Program of Shanxi Province (No. 141006) are gratefully acknowledged.

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Volume 71| Part 7| July 2015| Pages o506-o507

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