N2-o-Tolyl­benzamidine

Zhang, L.-Z.; Tong, H.-B.

doi:10.1107/S1600536808017625

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1276

doi:10.1107/S1600536808017625

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N²-o-Tolylbenzamidine

Li-Zeng Zhang ^a and Hong-Bo Tong ^a ^*

^aInstitute of Applied Chemistry, Shanxi University, Shanxi 030006, People's Republic of China
^*Correspondence e-mail: tong@sxu.edu.cn

(Received 2 June 2008; accepted 11 June 2008; online 19 June 2008)

The asymmetric unit of the title compound, C₁₄H₁₄N₂, contains two independent molecules with slightly different conformations; the dihedral angles formed by aromatic rings in the two molecules are 73.2 (1) and 75.0 (1)°. Intermolecular N—H⋯N hydrogen bonds link the molecules into chains extended in the [100] direction.

Related literature

For general background, see Bourget-Merle et al. (2002 ). For a related crystal structure, see Surma et al. (1988 ).

Experimental

Crystal data

C₁₄H₁₄N₂
M_r = 210.27
Triclinic, $[P \overline 1]$
a = 10.347 (2) Å
b = 10.697 (2) Å
c = 11.495 (2) Å
α = 97.088 (4)°
β = 103.184 (4)°
γ = 95.898 (4)°
V = 1218.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 298 (2) K
0.30 × 0.20 × 0.20 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ) T_min = 0.980, T_max = 0.986
4978 measured reflections
4158 independent reflections
2913 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.073
wR(F²) = 0.235
S = 1.09
4158 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯N3	0.86	2.25	3.049 (3)	156
N4—H4B⋯N1ⁱ	0.86	2.24	3.016 (3)	151
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808017625/cv2419sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808017625/cv2419Isup2.hkl

checkCIF report

Comment top

β-Diketiminate complexes are among the most common chelate systems in coordination chemistry (Bourget-Merle et al., 2002). Inspired by getting new chelate system with amidine motif, we got the title compound (I) by additional reaction of PhCN with o-methyl aniline lithium.

The asymmetric unit of (I) contains two independent molecules (Fig. 1), denoted A and B. The N=C bond lengths in both molecules (Table 1) agree well with the corresponding values reported for similar compounds (Surma et al., 1988). The conformations of the two independent molecules are slightly different. In molecule A, the mean plane N3/C22/N4 makes dihedral angles of 85.3 (1) and 21.5 (1)° with phenyl rings C16–C21and C23–C28, respectively. In molecule B, the mean plane N1/C8/N2 makes dihedral angles 86.8 (1) and 18.2 (1)° with phenyl rings C2–C7 and C9–C14, respectively.

In the crystal, intermolecular N—H···N hydrogen bonds (Table 1) link the molecules into chains extended in direction [100].

Related literature top

For general background, see Bourget-Merle et al. (2002). For a related crystal structure, see Surma et al. (1988).

Experimental top

All experiments were performed under an atmosphere of pure argon using Schlenk apparatus and a vacuum line, unless otherwise stated. The solvents used were of reagent grade or better and were freshly distilled under dry dinitrogen and degassed prior to use. Slowly added PhCN(1.03 g,10 mmol)to the solution of compound o-methyl-PhNHLi (1.13 g,10 mmol) in hexane (ca 40 ml)at -0°C., and then stirred for further 12 h.Add it to cold water, and then use chlorform to extract organic phase.The organic phase was slowly concentrated and get the crystal of the title compound.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Two independent molecules of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

N²-o-Tolylbenzamidine top

Crystal data top

C₁₄H₁₄N₂	Z = 4
M_r = 210.27	F(000) = 448
Triclinic, P1	D_x = 1.147 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.347 (2) Å	Cell parameters from 2024 reflections
b = 10.697 (2) Å	θ = 2.4–27.7°
c = 11.495 (2) Å	µ = 0.07 mm⁻¹
α = 97.088 (4)°	T = 298 K
β = 103.184 (4)°	Plate, colourless
γ = 95.898 (4)°	0.30 × 0.20 × 0.20 mm
V = 1218.0 (4) Å³

Data collection top

Siemens SMART CCD area-detector diffractometer	4158 independent reflections
Radiation source: fine-focus sealed tube	2913 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −10→12
T_min = 0.980, T_max = 0.986	k = −12→12
4978 measured reflections	l = −13→13

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.235	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.1497P)²] where P = (F_o² + 2F_c²)/3
4158 reflections	(Δ/σ)_max < 0.001
291 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₁₄H₁₄N₂	γ = 95.898 (4)°
M_r = 210.27	V = 1218.0 (4) Å³
Triclinic, P1	Z = 4
a = 10.347 (2) Å	Mo Kα radiation
b = 10.697 (2) Å	µ = 0.07 mm⁻¹
c = 11.495 (2) Å	T = 298 K
α = 97.088 (4)°	0.30 × 0.20 × 0.20 mm
β = 103.184 (4)°

Data collection top

Siemens SMART CCD area-detector diffractometer	4158 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	2913 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.986	R_int = 0.021
4978 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	0 restraints
wR(F²) = 0.235	H-atom parameters constrained
S = 1.09	Δρ_max = 0.44 e Å⁻³
4158 reflections	Δρ_min = −0.46 e Å⁻³
291 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	0.90491 (17)	0.79986 (19)	0.88806 (17)	0.0538 (5)
N2	0.69224 (19)	0.8197 (2)	0.9148 (2)	0.0688 (6)
H2A	0.6726	0.8582	0.8530	0.083*
H2B	0.6343	0.8055	0.9564	0.083*
C1	0.7749 (4)	0.6552 (3)	0.6545 (3)	0.1043 (12)
H1A	0.7196	0.6274	0.5744	0.156*
H1B	0.7251	0.6362	0.7126	0.156*
H1C	0.8527	0.6121	0.6659	0.156*
C2	0.8172 (3)	0.7949 (3)	0.6711 (2)	0.0644 (7)
C3	0.8023 (3)	0.8623 (3)	0.5739 (3)	0.0852 (9)
H3	0.7654	0.8180	0.4965	0.102*
C4	0.8387 (4)	0.9873 (4)	0.5865 (3)	0.0972 (11)
H4	0.8248	1.0285	0.5189	0.117*
C5	0.8971 (4)	1.0561 (3)	0.7000 (3)	0.0927 (10)
H5	0.9236	1.1433	0.7096	0.111*
C6	0.9149 (3)	0.9920 (3)	0.7983 (3)	0.0680 (7)
H6	0.9543	1.0371	0.8749	0.082*
C7	0.8762 (2)	0.8639 (2)	0.7862 (2)	0.0508 (6)
C8	0.81298 (19)	0.7817 (2)	0.9464 (2)	0.0478 (5)
C9	0.8415 (2)	0.7144 (2)	1.05346 (19)	0.0490 (6)
C10	0.9449 (3)	0.6419 (2)	1.0709 (2)	0.0647 (7)
H10	0.9974	0.6353	1.0152	0.078*
C11	0.9718 (3)	0.5790 (3)	1.1693 (3)	0.0786 (8)
H11	1.0427	0.5313	1.1796	0.094*
C12	0.8962 (3)	0.5858 (3)	1.2516 (3)	0.0787 (8)
H12	0.9148	0.5427	1.3177	0.094*
C13	0.7939 (3)	0.6555 (4)	1.2367 (3)	0.0889 (10)
H13	0.7411	0.6594	1.2922	0.107*
C14	0.7669 (3)	0.7217 (3)	1.1390 (3)	0.0772 (8)
H14	0.6977	0.7715	1.1312	0.093*
N3	0.42879 (17)	0.78365 (18)	0.99087 (16)	0.0513 (5)
N4	0.20510 (18)	0.8125 (2)	0.96875 (18)	0.0692 (7)
H4A	0.2161	0.8348	1.0452	0.083*
H4B	0.1275	0.8098	0.9206	0.083*
C15	0.3694 (4)	0.5807 (3)	1.1207 (3)	0.0896 (9)
H15A	0.3615	0.5260	1.1796	0.134*
H15B	0.4309	0.5519	1.0755	0.134*
H15C	0.2832	0.5790	1.0667	0.134*
C16	0.4201 (2)	0.7134 (3)	1.1833 (2)	0.0616 (7)
C17	0.4444 (3)	0.7462 (4)	1.3083 (3)	0.0825 (9)
H17	0.4277	0.6830	1.3538	0.099*
C18	0.4913 (3)	0.8661 (4)	1.3665 (3)	0.0901 (10)
H18	0.5050	0.8843	1.4500	0.108*
C19	0.5182 (3)	0.9601 (3)	1.3013 (3)	0.0863 (9)
H19	0.5513	1.0424	1.3405	0.104*
C20	0.4963 (2)	0.9325 (3)	1.1778 (2)	0.0642 (7)
H20	0.5155	0.9965	1.1340	0.077*
C21	0.44635 (19)	0.8118 (2)	1.1180 (2)	0.0495 (6)
C22	0.3093 (2)	0.7819 (2)	0.9244 (2)	0.0484 (6)
C23	0.2832 (2)	0.7442 (2)	0.7916 (2)	0.0515 (6)
C24	0.1744 (3)	0.7776 (3)	0.7119 (2)	0.0671 (7)
H24	0.1161	0.8262	0.7416	0.081*
C25	0.1519 (3)	0.7395 (3)	0.5887 (3)	0.0783 (8)
H25	0.0783	0.7621	0.5364	0.094*
C26	0.2365 (3)	0.6692 (3)	0.5435 (3)	0.0816 (9)
H26	0.2214	0.6442	0.4606	0.098*
C27	0.3439 (3)	0.6357 (3)	0.6208 (3)	0.0833 (9)
H27	0.4020	0.5878	0.5900	0.100*
C28	0.3671 (3)	0.6717 (3)	0.7434 (2)	0.0671 (7)
H28	0.4402	0.6471	0.7947	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0370 (9)	0.0696 (13)	0.0553 (11)	0.0099 (8)	0.0100 (8)	0.0120 (9)
N2	0.0402 (10)	0.0939 (16)	0.0826 (15)	0.0198 (10)	0.0210 (9)	0.0325 (12)
C1	0.136 (3)	0.0662 (19)	0.087 (2)	−0.0047 (19)	−0.008 (2)	0.0009 (16)
C2	0.0606 (15)	0.0661 (16)	0.0609 (16)	0.0095 (12)	0.0040 (12)	0.0082 (12)
C3	0.097 (2)	0.090 (2)	0.0601 (17)	0.0134 (18)	−0.0004 (15)	0.0146 (15)
C4	0.113 (3)	0.091 (2)	0.085 (2)	0.006 (2)	0.0080 (19)	0.0392 (19)
C5	0.104 (2)	0.0664 (18)	0.102 (3)	−0.0002 (17)	0.011 (2)	0.0254 (18)
C6	0.0624 (15)	0.0669 (17)	0.0694 (17)	0.0030 (12)	0.0100 (12)	0.0065 (13)
C7	0.0348 (10)	0.0583 (14)	0.0591 (14)	0.0068 (9)	0.0100 (9)	0.0097 (11)
C8	0.0341 (10)	0.0521 (12)	0.0541 (13)	0.0056 (9)	0.0086 (9)	0.0012 (10)
C9	0.0395 (11)	0.0524 (13)	0.0521 (13)	0.0010 (9)	0.0099 (9)	0.0036 (10)
C10	0.0629 (15)	0.0667 (15)	0.0732 (17)	0.0202 (12)	0.0252 (12)	0.0186 (13)
C11	0.084 (2)	0.0766 (19)	0.085 (2)	0.0262 (15)	0.0248 (16)	0.0298 (16)
C12	0.081 (2)	0.083 (2)	0.0711 (18)	0.0027 (16)	0.0123 (15)	0.0273 (15)
C13	0.081 (2)	0.129 (3)	0.0676 (18)	0.020 (2)	0.0328 (15)	0.0283 (18)
C14	0.0590 (16)	0.111 (2)	0.0723 (18)	0.0303 (16)	0.0254 (13)	0.0215 (16)
N3	0.0377 (10)	0.0634 (12)	0.0546 (11)	0.0068 (8)	0.0148 (8)	0.0084 (9)
N4	0.0381 (10)	0.1089 (17)	0.0584 (12)	0.0166 (11)	0.0105 (9)	0.0006 (12)
C15	0.102 (2)	0.0692 (19)	0.097 (2)	−0.0074 (16)	0.0294 (18)	0.0172 (16)
C16	0.0501 (13)	0.0753 (17)	0.0631 (16)	0.0099 (12)	0.0184 (11)	0.0142 (13)
C17	0.0803 (19)	0.113 (3)	0.0645 (18)	0.0232 (18)	0.0261 (15)	0.0285 (18)
C18	0.091 (2)	0.119 (3)	0.0580 (17)	0.020 (2)	0.0182 (16)	−0.0026 (19)
C19	0.083 (2)	0.092 (2)	0.074 (2)	0.0097 (17)	0.0135 (16)	−0.0152 (17)
C20	0.0555 (14)	0.0655 (16)	0.0695 (17)	0.0087 (12)	0.0147 (12)	0.0029 (13)
C21	0.0333 (10)	0.0609 (14)	0.0554 (14)	0.0077 (9)	0.0138 (9)	0.0066 (11)
C22	0.0373 (11)	0.0519 (12)	0.0572 (14)	0.0038 (9)	0.0151 (9)	0.0086 (10)
C23	0.0422 (12)	0.0549 (13)	0.0571 (14)	−0.0001 (10)	0.0140 (10)	0.0094 (10)
C24	0.0588 (15)	0.0825 (18)	0.0636 (16)	0.0168 (13)	0.0156 (12)	0.0177 (13)
C25	0.0736 (18)	0.097 (2)	0.0599 (17)	0.0079 (16)	0.0039 (14)	0.0204 (15)
C26	0.083 (2)	0.100 (2)	0.0561 (16)	−0.0026 (17)	0.0186 (15)	0.0018 (15)
C27	0.0714 (18)	0.102 (2)	0.0710 (19)	0.0136 (16)	0.0196 (15)	−0.0133 (16)
C28	0.0532 (14)	0.0801 (17)	0.0639 (16)	0.0121 (12)	0.0113 (12)	−0.0014 (13)

Geometric parameters (Å, º) top

N1—C8	1.295 (3)	N3—C22	1.294 (3)
N1—C7	1.417 (3)	N3—C21	1.421 (3)
N2—C8	1.338 (3)	N4—C22	1.346 (3)
N2—H2A	0.8600	N4—H4A	0.8600
N2—H2B	0.8600	N4—H4B	0.8600
C1—C2	1.490 (4)	C15—C16	1.493 (4)
C1—H1A	0.9600	C15—H15A	0.9600
C1—H1B	0.9600	C15—H15B	0.9600
C1—H1C	0.9600	C15—H15C	0.9600
C2—C3	1.391 (4)	C16—C17	1.394 (4)
C2—C7	1.402 (3)	C16—C21	1.405 (3)
C3—C4	1.332 (4)	C17—C18	1.357 (5)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.386 (5)	C18—C19	1.368 (5)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.379 (4)	C19—C20	1.375 (4)
C5—H5	0.9300	C19—H19	0.9300
C6—C7	1.369 (3)	C20—C21	1.374 (3)
C6—H6	0.9300	C20—H20	0.9300
C8—C9	1.489 (3)	C22—C23	1.485 (3)
C9—C10	1.377 (3)	C23—C28	1.384 (3)
C9—C14	1.381 (3)	C23—C24	1.388 (3)
C10—C11	1.375 (4)	C24—C25	1.383 (4)
C10—H10	0.9300	C24—H24	0.9300
C11—C12	1.359 (4)	C25—C26	1.359 (4)
C11—H11	0.9300	C25—H25	0.9300
C12—C13	1.347 (4)	C26—C27	1.364 (4)
C12—H12	0.9300	C26—H26	0.9300
C13—C14	1.391 (4)	C27—C28	1.373 (4)
C13—H13	0.9300	C27—H27	0.9300
C14—H14	0.9300	C28—H28	0.9300

C8—N1—C7	118.20 (18)	C22—N3—C21	116.93 (17)
C8—N2—H2A	120.0	C22—N4—H4A	120.0
C8—N2—H2B	120.0	C22—N4—H4B	120.0
H2A—N2—H2B	120.0	H4A—N4—H4B	120.0
C2—C1—H1A	109.5	C16—C15—H15A	109.5
C2—C1—H1B	109.5	C16—C15—H15B	109.5
H1A—C1—H1B	109.5	H15A—C15—H15B	109.5
C2—C1—H1C	109.5	C16—C15—H15C	109.5
H1A—C1—H1C	109.5	H15A—C15—H15C	109.5
H1B—C1—H1C	109.5	H15B—C15—H15C	109.5
C3—C2—C7	117.1 (3)	C17—C16—C21	116.7 (3)
C3—C2—C1	121.9 (3)	C17—C16—C15	122.3 (3)
C7—C2—C1	121.0 (3)	C21—C16—C15	121.1 (2)
C4—C3—C2	123.0 (3)	C18—C17—C16	122.9 (3)
C4—C3—H3	118.5	C18—C17—H17	118.5
C2—C3—H3	118.5	C16—C17—H17	118.5
C3—C4—C5	120.2 (3)	C17—C18—C19	119.4 (3)
C3—C4—H4	119.9	C17—C18—H18	120.3
C5—C4—H4	119.9	C19—C18—H18	120.3
C6—C5—C4	118.3 (3)	C18—C19—C20	119.8 (3)
C6—C5—H5	120.9	C18—C19—H19	120.1
C4—C5—H5	120.9	C20—C19—H19	120.1
C7—C6—C5	121.8 (3)	C21—C20—C19	121.0 (3)
C7—C6—H6	119.1	C21—C20—H20	119.5
C5—C6—H6	119.1	C19—C20—H20	119.5
C6—C7—C2	119.5 (2)	C20—C21—C16	120.1 (2)
C6—C7—N1	120.1 (2)	C20—C21—N3	120.4 (2)
C2—C7—N1	120.2 (2)	C16—C21—N3	119.4 (2)
N1—C8—N2	123.3 (2)	N3—C22—N4	123.7 (2)
N1—C8—C9	118.86 (18)	N3—C22—C23	119.19 (19)
N2—C8—C9	117.84 (19)	N4—C22—C23	117.14 (19)
C10—C9—C14	117.2 (2)	C28—C23—C24	117.7 (2)
C10—C9—C8	120.7 (2)	C28—C23—C22	120.2 (2)
C14—C9—C8	122.1 (2)	C24—C23—C22	122.1 (2)
C11—C10—C9	121.2 (3)	C25—C24—C23	120.7 (3)
C11—C10—H10	119.4	C25—C24—H24	119.7
C9—C10—H10	119.4	C23—C24—H24	119.7
C12—C11—C10	120.8 (3)	C26—C25—C24	120.5 (3)
C12—C11—H11	119.6	C26—C25—H25	119.8
C10—C11—H11	119.6	C24—C25—H25	119.8
C13—C12—C11	119.5 (3)	C25—C26—C27	119.5 (3)
C13—C12—H12	120.3	C25—C26—H26	120.2
C11—C12—H12	120.3	C27—C26—H26	120.2
C12—C13—C14	120.5 (3)	C26—C27—C28	120.8 (3)
C12—C13—H13	119.8	C26—C27—H27	119.6
C14—C13—H13	119.8	C28—C27—H27	119.6
C9—C14—C13	120.9 (3)	C27—C28—C23	120.9 (3)
C9—C14—H14	119.6	C27—C28—H28	119.6
C13—C14—H14	119.6	C23—C28—H28	119.6

C7—C2—C3—C4	−1.5 (5)	C21—C16—C17—C18	−0.1 (4)
C1—C2—C3—C4	179.6 (3)	C15—C16—C17—C18	179.6 (3)
C2—C3—C4—C5	1.5 (6)	C16—C17—C18—C19	−0.9 (5)
C3—C4—C5—C6	−0.6 (6)	C17—C18—C19—C20	0.7 (5)
C4—C5—C6—C7	−0.2 (5)	C18—C19—C20—C21	0.6 (4)
C5—C6—C7—C2	0.2 (4)	C19—C20—C21—C16	−1.6 (3)
C5—C6—C7—N1	175.4 (3)	C19—C20—C21—N3	−177.7 (2)
C3—C2—C7—C6	0.6 (4)	C17—C16—C21—C20	1.4 (3)
C1—C2—C7—C6	179.5 (3)	C15—C16—C21—C20	−178.3 (3)
C3—C2—C7—N1	−174.6 (2)	C17—C16—C21—N3	177.5 (2)
C1—C2—C7—N1	4.3 (4)	C15—C16—C21—N3	−2.2 (3)
C8—N1—C7—C6	95.6 (3)	C22—N3—C21—C20	−98.8 (2)
C8—N1—C7—C2	−89.2 (3)	C22—N3—C21—C16	85.1 (3)
C7—N1—C8—N2	0.4 (3)	C21—N3—C22—N4	4.2 (3)
C7—N1—C8—C9	179.91 (19)	C21—N3—C22—C23	−175.76 (19)
N1—C8—C9—C10	−18.2 (3)	N3—C22—C23—C28	22.1 (3)
N2—C8—C9—C10	161.3 (2)	N4—C22—C23—C28	−157.9 (2)
N1—C8—C9—C14	161.7 (2)	N3—C22—C23—C24	−159.0 (2)
N2—C8—C9—C14	−18.8 (3)	N4—C22—C23—C24	21.1 (3)
C14—C9—C10—C11	0.3 (4)	C28—C23—C24—C25	−0.1 (4)
C8—C9—C10—C11	−179.8 (2)	C22—C23—C24—C25	−179.1 (2)
C9—C10—C11—C12	0.6 (5)	C23—C24—C25—C26	−0.4 (4)
C10—C11—C12—C13	−0.3 (5)	C24—C25—C26—C27	0.4 (5)
C11—C12—C13—C14	−1.0 (5)	C25—C26—C27—C28	0.2 (5)
C10—C9—C14—C13	−1.5 (4)	C26—C27—C28—C23	−0.7 (5)
C8—C9—C14—C13	178.5 (3)	C24—C23—C28—C27	0.7 (4)
C12—C13—C14—C9	1.9 (5)	C22—C23—C28—C27	179.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N3	0.86	2.25	3.049 (3)	156
N4—H4B···N1ⁱ	0.86	2.24	3.016 (3)	151

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄N₂
M_r	210.27
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	10.347 (2), 10.697 (2), 11.495 (2)
α, β, γ (°)	97.088 (4), 103.184 (4), 95.898 (4)
V (Å³)	1218.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997)
T_min, T_max	0.980, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	4978, 4158, 2913
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.235, 1.09
No. of reflections	4158
No. of parameters	291
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.46

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N3	0.86	2.25	3.049 (3)	155.6
N4—H4B···N1ⁱ	0.86	2.24	3.016 (3)	150.5

Symmetry code: (i) x−1, y, z.

Acknowledgements

We thank the Youth Foundation of Shanxi University (grant No. 2006026, China) for financial support.

References

Bourget-Merle, L., Lappert, M. F. & Severn, J. R. (2002). Chem. Rev. 102, 3031–3065. Web of Science CrossRef PubMed CAS Google Scholar
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Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison Wisconsin, USA. Google Scholar
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