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organic compounds
of 1,2-bis(2,6-dimethylphenyl)-3-phenylguanidine
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
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
|
2.3. Refinement
|
|
Data collection: APEX2 (Bruker, 2007); cell 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
10.1107/S2056989015011822/pk2556sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989015011822/pk2556Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015011822/pk2556Isup3.cml
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
of which is presented here. In addition to two examples of phenyl-substituted benzimidazol (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].
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).
Crystal data, data collection and structure
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 Uiso (H) = 1.2 or 1.5Ueq (CMe).Data collection: APEX2 (Bruker, 2007); cell
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). ![]() | 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. |
C23H25N3 | F(000) = 736 |
Mr = 343.46 | Dx = 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 |
Bruker SMART CCD area-detector diffractometer | 3547 independent reflections |
Radiation source: fine-focus sealed tube | 2649 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ϕ and ω scans | θmax = 25.5°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −23→23 |
Tmin = 0.976, Tmax = 0.980 | k = −9→5 |
10737 measured reflections | l = −15→15 |
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(Fo2) + (0.0564P)2] where P = (Fo2 + 2Fc2)/3 |
3547 reflections | (Δ/σ)max = 0.001 |
239 parameters | Δρmax = 0.14 e Å−3 |
1 restraint | Δρmin = −0.14 e Å−3 |
C23H25N3 | V = 1966.0 (13) Å3 |
Mr = 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 |
Bruker SMART CCD area-detector diffractometer | 3547 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2649 reflections with I > 2σ(I) |
Tmin = 0.976, Tmax = 0.980 | Rint = 0.038 |
10737 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 1 restraint |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.14 e Å−3 |
3547 reflections | Δρmin = −0.14 e Å−3 |
239 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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) |
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. |
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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