4-[(4-Methyl­anilino)meth­yl]benzonitrile

Wei, B.

doi:10.1107/S1600536811020757

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1677

doi:10.1107/S1600536811020757

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4-[(4-Methylanilino)methyl]benzonitrile

Bin Wei ^a ^*

^aOrdered Matter Science Research Center, Southeast University, Nanjing 211189, People's Republic of China
^*Correspondence e-mail: seuwei@126.com

(Received 21 March 2011; accepted 30 May 2011; online 18 June 2011)

The asymmetric unit of the title compound, C₁₅H₁₄N₂, contains two molecules. The amine NH group connects two aromatic systems with similar C—N—C bond angles of 120.96 (16) and 119.75 (16)° for each independent molecule. In contrast, the dihedral angles between the benzene rings are significantly different for the two independent molecules, viz. 69.1 (2) and 79.9 (2)°.

Related literature

For related literature on dielectric–ferroelectric materials (the title compound is a candidate for having good dielectric properties), see: Chen et al. (2010 ); Wang et al. (2005 ); Xiong et al. (2002 ); Ye et al. (2006 ); Zhao et al. (2008 ).

Experimental

Crystal data

C₁₅H₁₄N₂
M_r = 222.28
Monoclinic, P 2₁ /c
a = 12.485 (3) Å
b = 9.112 (3) Å
c = 22.180 (6) Å
β = 98.537 (6)°
V = 2495.3 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.852, T_max = 1.000
21959 measured reflections
4394 independent reflections
3253 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.146
S = 1.12
4394 reflections
317 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811020757/bh2348sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020757/bh2348Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811020757/bh2348Isup3.cml

checkCIF report

Comment top

We are researching for dielectric-ferroelectric materials. Recent studies have revealed that small molecular compounds which have one or more amidogens probably have this kind of character (Chen et al., 2010). Thus, we want to find aromatic compounds containing amidogens, with the hope to obtain dielectric-ferroelectric properties (Xiong et al., 2002; Zhao et al., 2008). As part of our ongoing studies, we report here the crystal structure of the title compound. The dielectric constant of 4-[(p-tolylamino)methyl]benzonitrile as a function of temperature indicates that the permittivity is basically temperature-independent (Wang et al., 2005). After characterization of the dielectric constant, there is no dielectric anomaly observed (Ye et al., 2006). This compound thus should not be a real ferroelectrics or there may be no distinct phase transition occurring within the measured temperature range.

The asymmetric unit of the title compound contains two independent molecules (Fig. 1). The N atom connects two aromatic groups, with bond angles at N1 and N4 being 120.96 (16) and 119.75 (16)°, and the dihedral angle between two benzene rings being 69.1 (2) and 79.9 (2)°, respectively. In the crystal structure, very weak intermolecular interactions link molecules to form one-dimensional ladder propagating along the [010] direction (Fig. 2).

Related literature top

For related literature on dielectric-ferroelectric materials, see: Chen et al. (2010); Wang et al. (2005); Xiong et al. (2002); Ye et al. (2006); Zhao et al. (2008).

Experimental top

The title compound was obtained by addition of 6.6 g of (E)-4-[(p-tolylimino)methyl]benzonitrile (30 mmol) to a solution of 4.5 g of sodiumborohydride in THF, in the stoichiometric ratio 1:4. After reacting for 5 h in an ice bath, the mixture was filtered. Good quality single crystals were obtained by slow evaporation of the filtrate over two days.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Crystal structure of the title compound with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Crystal structure of the title compound with view along the a axis. Intermolecular interactions are shown as dashed lines.

4-[(4-Methylanilino)methyl]benzonitrile top

Crystal data top

C₁₅H₁₄N₂	Z = 8
M_r = 222.28	F(000) = 944
Monoclinic, P2₁/c	D_x = 1.183 Mg m⁻³
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.485 (3) Å	θ = 2.0–27.4°
b = 9.112 (3) Å	µ = 0.07 mm⁻¹
c = 22.180 (6) Å	T = 293 K
β = 98.537 (6)°	Prism, colourless
V = 2495.3 (12) Å³	0.20 × 0.20 × 0.20 mm

Data collection top

Rigaku Mercury CCD diffractometer	4394 independent reflections
Radiation source: fine-focus sealed tube	3253 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
Detector resolution: 28.5714 pixels mm^-1	θ_max = 25.0°, θ_min = 2.8°
ω scans	h = −14→14
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
T_min = 0.852, T_max = 1.000	l = −26→26
21959 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.059	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.146	w = 1/[σ²(F_o²) + (0.0641P)² + 0.2355P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max < 0.001
4394 reflections	Δρ_max = 0.13 e Å⁻³
317 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
0 constraints	Extinction coefficient: 0.014 (4)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₅H₁₄N₂	V = 2495.3 (12) Å³
M_r = 222.28	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.485 (3) Å	µ = 0.07 mm⁻¹
b = 9.112 (3) Å	T = 293 K
c = 22.180 (6) Å	0.20 × 0.20 × 0.20 mm
β = 98.537 (6)°

Data collection top

Rigaku Mercury CCD diffractometer	4394 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	3253 reflections with I > 2σ(I)
T_min = 0.852, T_max = 1.000	R_int = 0.049
21959 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	Δρ_max = 0.13 e Å⁻³
4394 reflections	Δρ_min = −0.18 e Å⁻³
317 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.9872 (2)	0.3906 (3)	0.28894 (9)	0.0798 (7)
H1A	1.0443	0.4621	0.2932	0.120*	0.64 (3)
H1B	1.0158	0.2974	0.3038	0.120*	0.64 (3)
H1C	0.9318	0.4211	0.3120	0.120*	0.64 (3)
H1D	1.0630	0.3672	0.2940	0.120*	0.36 (3)
H1E	0.9509	0.3241	0.3127	0.120*	0.36 (3)
H1F	0.9780	0.4894	0.3024	0.120*	0.36 (3)
C2	0.93940 (16)	0.3767 (2)	0.22236 (9)	0.0608 (5)
C3	0.97256 (17)	0.4659 (2)	0.17850 (9)	0.0665 (5)
H3A	1.0262	0.5353	0.1904	0.080*
C4	0.92924 (16)	0.4564 (2)	0.11736 (9)	0.0625 (5)
H4A	0.9538	0.5189	0.0892	0.075*
C5	0.84884 (15)	0.3534 (2)	0.09788 (8)	0.0536 (5)
C6	0.81507 (15)	0.2625 (2)	0.14188 (8)	0.0588 (5)
H6A	0.7616	0.1928	0.1303	0.071*
C7	0.85965 (17)	0.2745 (2)	0.20223 (9)	0.0629 (5)
H7A	0.8355	0.2119	0.2305	0.075*
C8	0.8210 (2)	0.4451 (2)	−0.00775 (9)	0.0804 (7)
H8A	0.8976	0.4521	−0.0106	0.097*
H8B	0.7972	0.5399	0.0052	0.097*
C9	0.75965 (18)	0.4082 (2)	−0.06918 (8)	0.0626 (5)
C10	0.6848 (2)	0.5044 (2)	−0.09876 (10)	0.0734 (6)
H10A	0.6720	0.5929	−0.0802	0.088*
C11	0.62855 (18)	0.4722 (2)	−0.15532 (10)	0.0727 (6)
H11A	0.5788	0.5389	−0.1750	0.087*
C12	0.64640 (15)	0.3395 (2)	−0.18292 (8)	0.0579 (5)
C13	0.72085 (17)	0.2422 (2)	−0.15366 (9)	0.0655 (6)
H13A	0.7334	0.1533	−0.1720	0.079*
C14	0.77679 (19)	0.2767 (2)	−0.09725 (9)	0.0718 (6)
H14A	0.8269	0.2103	−0.0777	0.086*
C15	0.58706 (17)	0.3040 (2)	−0.24151 (10)	0.0689 (6)
C16	0.49515 (19)	0.2565 (3)	0.46950 (11)	0.0853 (7)
C17	0.42565 (16)	0.2503 (3)	0.41163 (9)	0.0661 (6)
C18	0.40122 (17)	0.3763 (3)	0.37803 (9)	0.0706 (6)
H18A	0.4282	0.4663	0.3931	0.085*
C19	0.33690 (17)	0.3687 (2)	0.32206 (9)	0.0658 (5)
H19A	0.3208	0.4542	0.2997	0.079*
C20	0.29561 (15)	0.2362 (2)	0.29845 (8)	0.0567 (5)
C21	0.31974 (17)	0.1112 (2)	0.33292 (9)	0.0709 (6)
H21A	0.2922	0.0214	0.3179	0.085*
C22	0.38393 (18)	0.1168 (3)	0.38921 (10)	0.0744 (6)
H22A	0.3991	0.0315	0.4119	0.089*
C23	0.22708 (16)	0.2286 (2)	0.23680 (8)	0.0643 (5)
H23A	0.1588	0.1809	0.2404	0.077*
H23B	0.2115	0.3271	0.2214	0.077*
C24	0.23994 (15)	0.14312 (19)	0.13250 (8)	0.0522 (5)
C25	0.30602 (16)	0.0980 (2)	0.09069 (9)	0.0622 (5)
H25A	0.3780	0.0742	0.1042	0.075*
C26	0.26565 (17)	0.0883 (2)	0.02950 (9)	0.0633 (5)
H26A	0.3114	0.0572	0.0026	0.076*
C27	0.15952 (17)	0.1231 (2)	0.00676 (8)	0.0581 (5)
C28	0.09473 (16)	0.1671 (2)	0.04877 (8)	0.0619 (5)
H28A	0.0228	0.1908	0.0352	0.074*
C29	0.13339 (15)	0.1772 (2)	0.11060 (8)	0.0578 (5)
H29A	0.0872	0.2071	0.1375	0.069*
C30	0.1177 (2)	0.1150 (3)	−0.06047 (9)	0.0811 (7)
H30A	0.0513	0.0600	−0.0667	0.122*	0.34 (3)
H30B	0.1704	0.0674	−0.0812	0.122*	0.34 (3)
H30C	0.1046	0.2124	−0.0764	0.122*	0.34 (3)
H30D	0.0445	0.1505	−0.0678	0.122*	0.66 (3)
H30E	0.1195	0.0150	−0.0739	0.122*	0.66 (3)
H30F	0.1623	0.1743	−0.0825	0.122*	0.66 (3)
H1	0.740 (2)	0.293 (3)	0.0310 (11)	0.122*
H4	0.354 (2)	0.159 (3)	0.2001 (12)	0.122*
N1	0.80476 (15)	0.33596 (19)	0.03692 (7)	0.0656 (5)
N2	0.54010 (17)	0.2771 (2)	−0.28871 (9)	0.0944 (7)
N3	0.55062 (18)	0.2632 (3)	0.51543 (10)	0.1172 (9)
N4	0.28294 (13)	0.14703 (19)	0.19445 (7)	0.0636 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0882 (16)	0.0877 (16)	0.0595 (13)	0.0102 (13)	−0.0023 (12)	−0.0138 (11)
C2	0.0620 (12)	0.0629 (12)	0.0554 (12)	0.0112 (10)	0.0021 (9)	−0.0097 (10)
C3	0.0646 (13)	0.0650 (13)	0.0667 (13)	−0.0053 (10)	−0.0003 (10)	−0.0116 (10)
C4	0.0656 (12)	0.0618 (12)	0.0596 (12)	−0.0097 (10)	0.0081 (10)	−0.0022 (9)
C5	0.0537 (11)	0.0557 (11)	0.0508 (11)	0.0015 (9)	0.0052 (8)	−0.0043 (9)
C6	0.0603 (12)	0.0583 (12)	0.0569 (12)	−0.0062 (9)	0.0058 (9)	−0.0012 (9)
C7	0.0701 (13)	0.0648 (13)	0.0538 (12)	0.0041 (10)	0.0094 (10)	0.0008 (9)
C8	0.1052 (18)	0.0767 (15)	0.0574 (13)	−0.0287 (13)	0.0055 (12)	0.0054 (11)
C9	0.0786 (14)	0.0583 (12)	0.0503 (11)	−0.0117 (11)	0.0077 (10)	0.0082 (9)
C10	0.1007 (17)	0.0545 (12)	0.0661 (14)	0.0003 (12)	0.0161 (13)	0.0035 (10)
C11	0.0747 (14)	0.0653 (14)	0.0772 (15)	0.0119 (11)	0.0087 (12)	0.0165 (11)
C12	0.0556 (11)	0.0634 (13)	0.0544 (12)	−0.0046 (10)	0.0071 (9)	0.0118 (9)
C13	0.0760 (14)	0.0616 (12)	0.0583 (12)	0.0082 (11)	0.0073 (10)	0.0033 (10)
C14	0.0795 (15)	0.0708 (14)	0.0607 (13)	0.0113 (11)	−0.0045 (11)	0.0077 (11)
C15	0.0598 (12)	0.0799 (15)	0.0646 (14)	−0.0101 (11)	0.0016 (11)	0.0125 (11)
C16	0.0597 (13)	0.130 (2)	0.0653 (15)	0.0097 (14)	0.0042 (12)	−0.0150 (14)
C17	0.0509 (11)	0.0955 (16)	0.0517 (12)	−0.0010 (11)	0.0069 (9)	−0.0084 (11)
C18	0.0665 (13)	0.0782 (15)	0.0670 (14)	−0.0130 (11)	0.0096 (11)	−0.0159 (12)
C19	0.0714 (13)	0.0663 (13)	0.0599 (12)	−0.0089 (11)	0.0099 (10)	−0.0017 (10)
C20	0.0530 (11)	0.0674 (13)	0.0511 (11)	−0.0063 (9)	0.0120 (9)	−0.0053 (9)
C21	0.0746 (14)	0.0671 (13)	0.0684 (14)	−0.0136 (11)	0.0024 (11)	−0.0005 (11)
C22	0.0745 (14)	0.0821 (15)	0.0652 (14)	0.0006 (12)	0.0058 (11)	0.0120 (12)
C23	0.0615 (12)	0.0778 (14)	0.0533 (12)	0.0001 (10)	0.0068 (9)	−0.0070 (10)
C24	0.0544 (11)	0.0540 (11)	0.0482 (10)	−0.0010 (9)	0.0079 (8)	−0.0002 (8)
C25	0.0555 (11)	0.0691 (13)	0.0621 (13)	0.0080 (10)	0.0094 (9)	−0.0012 (10)
C26	0.0717 (13)	0.0656 (13)	0.0557 (12)	0.0034 (10)	0.0202 (10)	−0.0024 (9)
C27	0.0667 (12)	0.0562 (11)	0.0515 (11)	−0.0053 (10)	0.0089 (9)	0.0009 (9)
C28	0.0571 (12)	0.0709 (13)	0.0562 (12)	−0.0011 (10)	0.0037 (9)	0.0017 (10)
C29	0.0526 (11)	0.0662 (12)	0.0556 (12)	−0.0003 (9)	0.0108 (9)	−0.0030 (9)
C30	0.0943 (17)	0.0935 (17)	0.0539 (13)	−0.0065 (14)	0.0063 (11)	−0.0026 (11)
N1	0.0718 (11)	0.0724 (12)	0.0503 (10)	−0.0175 (9)	0.0019 (8)	0.0036 (8)
N2	0.0813 (14)	0.1146 (17)	0.0808 (14)	−0.0171 (12)	−0.0097 (11)	0.0060 (12)
N3	0.0791 (15)	0.188 (3)	0.0772 (15)	0.0210 (16)	−0.0122 (12)	−0.0228 (15)
N4	0.0592 (10)	0.0786 (12)	0.0522 (10)	0.0077 (9)	0.0048 (8)	−0.0078 (8)

Geometric parameters (Å, º) top

C1—C2	1.514 (2)	C16—C17	1.440 (3)
C1—H1A	0.9600	C17—C18	1.379 (3)
C1—H1B	0.9600	C17—C22	1.386 (3)
C1—H1C	0.9600	C18—C19	1.376 (3)
C1—H1D	0.9600	C18—H18A	0.9300
C1—H1E	0.9600	C19—C20	1.385 (3)
C1—H1F	0.9600	C19—H19A	0.9300
C2—C3	1.378 (3)	C20—C21	1.379 (3)
C2—C7	1.388 (3)	C20—C23	1.503 (2)
C3—C4	1.386 (3)	C21—C22	1.381 (3)
C3—H3A	0.9300	C21—H21A	0.9300
C4—C5	1.395 (3)	C22—H22A	0.9300
C4—H4A	0.9300	C23—N4	1.454 (2)
C5—N1	1.391 (2)	C23—H23A	0.9700
C5—C6	1.392 (3)	C23—H23B	0.9700
C6—C7	1.376 (2)	C24—C29	1.382 (3)
C6—H6A	0.9300	C24—C25	1.392 (3)
C7—H7A	0.9300	C24—N4	1.400 (2)
C8—N1	1.439 (3)	C25—C26	1.379 (2)
C8—C9	1.499 (3)	C25—H25A	0.9300
C8—H8A	0.9700	C26—C27	1.383 (3)
C8—H8B	0.9700	C26—H26A	0.9300
C9—C10	1.374 (3)	C27—C28	1.381 (3)
C9—C14	1.382 (3)	C27—C30	1.507 (3)
C10—C11	1.376 (3)	C28—C29	1.388 (2)
C10—H10A	0.9300	C28—H28A	0.9300
C11—C12	1.388 (3)	C29—H29A	0.9300
C11—H11A	0.9300	C30—H30A	0.9600
C12—C13	1.375 (3)	C30—H30B	0.9600
C12—C15	1.434 (3)	C30—H30C	0.9600
C13—C14	1.376 (3)	C30—H30D	0.9600
C13—H13A	0.9300	C30—H30E	0.9600
C14—H14A	0.9300	C30—H30F	0.9600
C15—N2	1.148 (2)	N1—H1	0.90 (3)
C16—N3	1.145 (3)	N4—H4	0.89 (3)

C2—C1—H1A	109.5	C22—C17—C16	119.9 (2)
C2—C1—H1B	109.5	C19—C18—C17	119.9 (2)
C2—C1—H1C	109.5	C19—C18—H18A	120.1
C2—C1—H1D	109.5	C17—C18—H18A	120.1
C2—C1—H1E	109.5	C18—C19—C20	121.3 (2)
H1D—C1—H1E	109.5	C18—C19—H19A	119.3
C2—C1—H1F	109.5	C20—C19—H19A	119.3
H1D—C1—H1F	109.5	C21—C20—C19	118.14 (19)
H1E—C1—H1F	109.5	C21—C20—C23	120.93 (18)
C3—C2—C7	116.44 (18)	C19—C20—C23	120.93 (18)
C3—C2—C1	121.55 (19)	C20—C21—C22	121.4 (2)
C7—C2—C1	122.0 (2)	C20—C21—H21A	119.3
C2—C3—C4	122.65 (19)	C22—C21—H21A	119.3
C2—C3—H3A	118.7	C21—C22—C17	119.5 (2)
C4—C3—H3A	118.7	C21—C22—H22A	120.2
C3—C4—C5	120.22 (19)	C17—C22—H22A	120.2
C3—C4—H4A	119.9	N4—C23—C20	110.39 (16)
C5—C4—H4A	119.9	N4—C23—H23A	109.6
N1—C5—C6	119.75 (17)	C20—C23—H23A	109.6
N1—C5—C4	122.71 (18)	N4—C23—H23B	109.6
C6—C5—C4	117.51 (17)	C20—C23—H23B	109.6
C7—C6—C5	120.96 (18)	H23A—C23—H23B	108.1
C7—C6—H6A	119.5	C29—C24—C25	117.85 (17)
C5—C6—H6A	119.5	C29—C24—N4	123.25 (17)
C6—C7—C2	122.22 (19)	C25—C24—N4	118.87 (17)
C6—C7—H7A	118.9	C26—C25—C24	120.57 (18)
C2—C7—H7A	118.9	C26—C25—H25A	119.7
N1—C8—C9	111.46 (17)	C24—C25—H25A	119.7
N1—C8—H8A	109.3	C25—C26—C27	122.33 (18)
C9—C8—H8A	109.3	C25—C26—H26A	118.8
N1—C8—H8B	109.3	C27—C26—H26A	118.8
C9—C8—H8B	109.3	C28—C27—C26	116.49 (18)
H8A—C8—H8B	108.0	C28—C27—C30	122.01 (19)
C10—C9—C14	118.53 (19)	C26—C27—C30	121.50 (19)
C10—C9—C8	120.7 (2)	C27—C28—C29	122.23 (18)
C14—C9—C8	120.78 (19)	C27—C28—H28A	118.9
C9—C10—C11	121.2 (2)	C29—C28—H28A	118.9
C9—C10—H10A	119.4	C24—C29—C28	120.53 (18)
C11—C10—H10A	119.4	C24—C29—H29A	119.7
C10—C11—C12	119.63 (19)	C28—C29—H29A	119.7
C10—C11—H11A	120.2	C27—C30—H30A	109.5
C12—C11—H11A	120.2	C27—C30—H30B	109.5
C13—C12—C11	119.65 (19)	C27—C30—H30C	109.5
C13—C12—C15	120.27 (19)	C27—C30—H30D	109.5
C11—C12—C15	120.08 (18)	C27—C30—H30E	109.5
C12—C13—C14	119.9 (2)	H30D—C30—H30E	109.5
C12—C13—H13A	120.0	C27—C30—H30F	109.5
C14—C13—H13A	120.0	H30D—C30—H30F	109.5
C13—C14—C9	121.05 (19)	H30E—C30—H30F	109.5
C13—C14—H14A	119.5	C5—N1—C8	120.96 (16)
C9—C14—H14A	119.5	C5—N1—H1	114.4 (17)
N2—C15—C12	179.1 (2)	C8—N1—H1	114.8 (17)
N3—C16—C17	179.2 (3)	C24—N4—C23	119.75 (16)
C18—C17—C22	119.74 (19)	C24—N4—H4	111.8 (17)
C18—C17—C16	120.3 (2)	C23—N4—H4	114.3 (18)

C7—C2—C3—C4	0.4 (3)	C18—C19—C20—C21	0.7 (3)
C1—C2—C3—C4	−179.28 (19)	C18—C19—C20—C23	−178.89 (18)
C2—C3—C4—C5	−0.1 (3)	C19—C20—C21—C22	−0.5 (3)
C3—C4—C5—N1	−178.02 (18)	C23—C20—C21—C22	179.04 (18)
C3—C4—C5—C6	−0.1 (3)	C20—C21—C22—C17	−0.3 (3)
N1—C5—C6—C7	178.03 (18)	C18—C17—C22—C21	1.1 (3)
C4—C5—C6—C7	0.0 (3)	C16—C17—C22—C21	−178.25 (19)
C5—C6—C7—C2	0.2 (3)	C21—C20—C23—N4	−65.8 (2)
C3—C2—C7—C6	−0.4 (3)	C19—C20—C23—N4	113.7 (2)
C1—C2—C7—C6	179.23 (18)	C29—C24—C25—C26	0.1 (3)
N1—C8—C9—C10	122.3 (2)	N4—C24—C25—C26	177.96 (18)
N1—C8—C9—C14	−57.5 (3)	C24—C25—C26—C27	0.4 (3)
C14—C9—C10—C11	−0.6 (3)	C25—C26—C27—C28	−0.7 (3)
C8—C9—C10—C11	179.60 (19)	C25—C26—C27—C30	178.61 (19)
C9—C10—C11—C12	0.8 (3)	C26—C27—C28—C29	0.4 (3)
C10—C11—C12—C13	−0.5 (3)	C30—C27—C28—C29	−178.88 (19)
C10—C11—C12—C15	179.14 (19)	C25—C24—C29—C28	−0.4 (3)
C11—C12—C13—C14	0.2 (3)	N4—C24—C29—C28	−178.12 (17)
C15—C12—C13—C14	−179.46 (18)	C27—C28—C29—C24	0.1 (3)
C12—C13—C14—C9	−0.1 (3)	C6—C5—N1—C8	167.4 (2)
C10—C9—C14—C13	0.3 (3)	C4—C5—N1—C8	−14.7 (3)
C8—C9—C14—C13	−179.9 (2)	C9—C8—N1—C5	−175.91 (19)
C22—C17—C18—C19	−0.9 (3)	C29—C24—N4—C23	−18.5 (3)
C16—C17—C18—C19	178.38 (18)	C25—C24—N4—C23	163.85 (19)
C17—C18—C19—C20	0.1 (3)	C20—C23—N4—C24	−171.62 (16)

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂
M_r	222.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.485 (3), 9.112 (3), 22.180 (6)
β (°)	98.537 (6)
V (Å³)	2495.3 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku Mercury CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.852, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	21959, 4394, 3253
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.146, 1.12
No. of reflections	4394
No. of parameters	317
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.18

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The author is grateful to the starter fund of Southeast University for the purchase of the diffractometer.

References

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