N,N-Diethyl-4-[1-phenyl-3-(pyridin-2-yl)-4,5-di­hydro-1H-pyrazol-5-yl]aniline

Zhu, Y.-Z.; Wang, H.; Sun, P.-P.; Tian, Y.-P.

doi:10.1107/S1600536813019879

organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1316

doi:10.1107/S1600536813019879

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N,N-Diethyl-4-[1-phenyl-3-(pyridin-2-yl)-4,5-dihydro-1H-pyrazol-5-yl]aniline

Ying-Zhong Zhu,^a,^b Hui Wang,^a,^b Ping-Ping Sun ^a,^b and Yu-Peng Tian ^a,^b ^*

^aDepartment of Chemistry, Anhui University, Hefei 230039, People's Republic of China, and ^bKey Laboratory of Functional Inorganic Materials Chemistry, Hefei 230039, People's Republic of China
^*Correspondence e-mail: yptian@ahu.edu.cn

(Received 23 June 2013; accepted 18 July 2013; online 27 July 2013)

In the title molecule, C₂₄H₂₆N₄, the pyrazoline ring assumes an envelope conformation with the aniline-bearing C atom at the flap position. The benzene ring and the pyridine ring form with the pyrazoline ring dihedral angles of 4.53 (1) and 6.26 (1)°, respectively. In turn, the aniline group is nearly perpendicular to the pyrazoline ring [dihedral angle = 79.96 (1)°]. The ethyl groups of the diethylamine substituent are disordered over two sets of sites, with an occupancy ratio of 0.624 (8):0.376 (8).

Related literature

For background to the design and synthesis of the title compound and for related structures, see: Chen et al. (2008 ); Dong et al. (2010 ); Guo et al. (2010 ); Liu et al. (2010 ).

Experimental

Crystal data

C₂₄H₂₆N₄
M_r = 370.49
Monoclinic, P 2₁ /c
a = 14.902 (5) Å
b = 11.314 (5) Å
c = 12.479 (5) Å
β = 94.644 (5)°
V = 2097.1 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 296 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.979, T_max = 0.986
14365 measured reflections
3678 independent reflections
2511 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.073
wR(F²) = 0.241
S = 1.06
3678 reflections
294 parameters
507 restraints
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813019879/gk2584sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813019879/gk2584Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813019879/gk2584Isup3.cml

checkCIF report

Comment top

The derivatives of the title compound are often used in medicinal chemistry and biochemistry (Guo et al. 2010; Liu et al. 2010). Herewith , in this study, we report the crystal structure of the title compound.

The pyrazoline ring is nearly coplanar to the benzene ring and the pyridine ring, with the dihedral angles of 4.53 (1)° and 6.26 (1)°, respectively (Fig.1). The anilinegroup is almost perpendicular to the pyrazoline ring, with a dihedral angle of 79.96 (1)°. The ethyl groups of the N,N-diethylaniline unit are disordered.

Related literature top

For background to the design and synthesis of the title compound, see: Chen et al. (2008); Dong et al. (2010); Guo et al. (2010); Liu et al. (2010).

Experimental top

A mixture of 3-(4-(diethylamino)phenyl)-1-(pyridin-2-yl)prop-2-en-1-one (2.8 g, 10 mmol), phenylhydrazine (1.5 ml) and acetic acid (10 ml) was refluxed for 4 h, cooled and Na₂CO₃ was added to modify the pH under vigorously stirring. to pH = 7. The mixture was washed with dichloromethane and the solution was evaporated and the crude product was obtained and purified by flash column chromatography (silica, 10:1 petroleum ether: ethyl acetate) to obtain light yellow crystals. Yiels: 40%. ¹H NMR (400 MHz, DMSO-d⁶) 1.03 (t, 6H), 3.11 (q, 1H), 3.25 (q, 4H), 3.86 (q, 1H) 5.37 (q, 1H), 6.57 (d, 2H), 6.74 (t, 1H), 7.06(q, 4H), 7,17(t, 2H), 7.30 (t, 1H), 7.82 (t, 1H) 8.09 (d, 1H), 8.54 (d, 1H).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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. The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted.

N,N-Diethyl-4-[1-phenyl-3-(pyridin-2-yl)-4,5-dihydro-1H-pyrazol-5-yl]aniline top

Crystal data top

C₂₄H₂₆N₄	F(000) = 792
M_r = 370.49	D_x = 1.173 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 391 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71069 Å
a = 14.902 (5) Å	Cell parameters from 3174 reflections
b = 11.314 (5) Å	θ = 2.4–23.1°
c = 12.479 (5) Å	µ = 0.07 mm⁻¹
β = 94.644 (5)°	T = 296 K
V = 2097.1 (14) Å³	Block, yellow
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker SMART APEX CCD diffractometer	3678 independent reflections
Radiation source: fine-focus sealed tube	2511 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −17→17
T_min = 0.979, T_max = 0.986	k = −13→13
14365 measured reflections	l = −14→14

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) = 0.241	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.1447P)² + 0.5666P] where P = (F_o² + 2F_c²)/3
3678 reflections	(Δ/σ)_max = 0.002
294 parameters	Δρ_max = 0.37 e Å⁻³
507 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

C₂₄H₂₆N₄	V = 2097.1 (14) Å³
M_r = 370.49	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.902 (5) Å	µ = 0.07 mm⁻¹
b = 11.314 (5) Å	T = 296 K
c = 12.479 (5) Å	0.30 × 0.20 × 0.20 mm
β = 94.644 (5)°

Data collection top

Bruker SMART APEX CCD diffractometer	3678 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2511 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.986	R_int = 0.038
14365 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	507 restraints
wR(F²) = 0.241	H-atom parameters constrained
S = 1.06	Δρ_max = 0.37 e Å⁻³
3678 reflections	Δρ_min = −0.52 e Å⁻³
294 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	Occ. (<1)
C1	0.3073 (2)	−0.2820 (3)	0.4677 (3)	0.0539 (7)
C2	0.3140 (2)	−0.3449 (3)	0.5624 (3)	0.0662 (9)
H2	0.3316	−0.3074	0.6271	0.079*
C3	0.2946 (3)	−0.4632 (3)	0.5606 (4)	0.0815 (10)
H3	0.3000	−0.5071	0.6239	0.098*
C4	0.2674 (3)	−0.5163 (4)	0.4651 (4)	0.0864 (11)
H4	0.2538	−0.5965	0.4616	0.104*
C5	0.2611 (3)	−0.4473 (4)	0.3752 (4)	0.0821 (11)
H5	0.2423	−0.4835	0.3103	0.099*
C6	0.32889 (19)	−0.1562 (3)	0.4637 (2)	0.0504 (7)
C7	0.3245 (2)	−0.0819 (3)	0.3641 (2)	0.0561 (8)
H7A	0.2659	−0.0876	0.3245	0.067*
H7B	0.3706	−0.1047	0.3175	0.067*
C8	0.3415 (2)	0.0433 (3)	0.4096 (2)	0.0519 (7)
H8	0.3888	0.0822	0.3723	0.062*
C9	0.40911 (18)	0.0948 (2)	0.5983 (2)	0.0485 (7)
C10	0.4309 (2)	0.2102 (3)	0.5699 (3)	0.0597 (8)
H10	0.4198	0.2357	0.4992	0.072*
C11	0.4691 (2)	0.2863 (3)	0.6473 (3)	0.0625 (8)
H11	0.4848	0.3623	0.6275	0.075*
C12	0.4846 (2)	0.2523 (3)	0.7527 (3)	0.0633 (8)
H12	0.5106	0.3043	0.8039	0.076*
C13	0.4608 (2)	0.1400 (3)	0.7814 (3)	0.0610 (8)
H13	0.4703	0.1164	0.8528	0.073*
C14	0.4230 (2)	0.0613 (3)	0.7055 (2)	0.0529 (7)
H14	0.4069	−0.0142	0.7264	0.064*
C15	0.2580 (2)	0.1196 (3)	0.4035 (2)	0.0504 (7)
C16	0.2344 (2)	0.1879 (3)	0.3139 (3)	0.0572 (8)
H16	0.2736	0.1927	0.2597	0.069*
C17	0.1544 (2)	0.2488 (3)	0.3028 (3)	0.0670 (9)
H17	0.1410	0.2942	0.2415	0.080*
C18	0.0926 (3)	0.2446 (3)	0.3813 (3)	0.0760 (9)
C19	0.1985 (2)	0.1174 (3)	0.4831 (3)	0.0656 (9)
H19	0.2132	0.0738	0.5452	0.079*
C20	0.1182 (3)	0.1780 (4)	0.4727 (3)	0.0767 (10)
H20	0.0801	0.1744	0.5280	0.092*
C21	−0.0287 (6)	0.3410 (9)	0.2615 (7)	0.1169 (19)	0.624 (8)
H21A	0.0049	0.3045	0.2069	0.140*	0.624 (8)
H21B	−0.0903	0.3128	0.2514	0.140*	0.624 (8)
C22	−0.0282 (8)	0.4663 (10)	0.2471 (10)	0.151 (3)	0.624 (8)
H22A	−0.0691	0.5022	0.2931	0.227*	0.624 (8)
H22B	−0.0465	0.4849	0.1735	0.227*	0.624 (8)
H22C	0.0315	0.4961	0.2651	0.227*	0.624 (8)
C23	−0.0521 (6)	0.2931 (9)	0.4622 (8)	0.1072 (18)	0.624 (8)
H23A	−0.0175	0.3015	0.5310	0.129*	0.624 (8)
H23B	−0.0961	0.3564	0.4556	0.129*	0.624 (8)
C24	−0.1004 (7)	0.1750 (9)	0.4583 (10)	0.127 (2)	0.624 (8)
H24A	−0.1462	0.1748	0.3995	0.190*	0.624 (8)
H24B	−0.1277	0.1627	0.5245	0.190*	0.624 (8)
H24C	−0.0580	0.1129	0.4483	0.190*	0.624 (8)
C21'	−0.0141 (8)	0.4066 (13)	0.2996 (14)	0.118 (2)	0.376 (8)
H21C	0.0205	0.3986	0.2373	0.142*	0.376 (8)
H21D	−0.0766	0.3947	0.2739	0.142*	0.376 (8)
C22'	−0.0068 (15)	0.5244 (13)	0.3306 (17)	0.146 (3)	0.376 (8)
H22D	−0.0077	0.5736	0.2679	0.219*	0.376 (8)
H22E	0.0488	0.5360	0.3739	0.219*	0.376 (8)
H22F	−0.0563	0.5449	0.3715	0.219*	0.376 (8)
C23'	−0.0689 (11)	0.2690 (15)	0.4247 (14)	0.108 (2)	0.376 (8)
H23C	−0.1125	0.3326	0.4158	0.129*	0.376 (8)
H23D	−0.0518	0.2612	0.5010	0.129*	0.376 (8)
C24'	−0.1138 (11)	0.1567 (14)	0.3859 (17)	0.128 (3)	0.376 (8)
H24D	−0.1529	0.1725	0.3226	0.191*	0.376 (8)
H24E	−0.1483	0.1253	0.4410	0.191*	0.376 (8)
H24F	−0.0689	0.1002	0.3692	0.191*	0.376 (8)
N1	0.0113 (3)	0.3032 (4)	0.3708 (4)	0.1077 (11)
N2	0.37522 (17)	0.0154 (2)	0.5210 (2)	0.0555 (7)
N3	0.35871 (16)	−0.0994 (2)	0.5487 (2)	0.0502 (7)
N4	0.2797 (2)	−0.3311 (3)	0.3729 (2)	0.0696 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0467 (15)	0.0507 (15)	0.0640 (17)	0.0005 (12)	0.0025 (13)	−0.0102 (13)
C2	0.0719 (19)	0.0515 (16)	0.0733 (18)	−0.0062 (14)	−0.0061 (15)	−0.0017 (14)
C3	0.093 (2)	0.0560 (18)	0.093 (2)	−0.0094 (17)	−0.0055 (19)	0.0011 (16)
C4	0.091 (2)	0.060 (2)	0.107 (2)	−0.0093 (18)	0.000 (2)	−0.0174 (17)
C5	0.085 (2)	0.070 (2)	0.091 (2)	−0.0079 (19)	0.0039 (19)	−0.0321 (18)
C6	0.0451 (14)	0.0499 (15)	0.0558 (16)	0.0017 (12)	0.0025 (12)	−0.0043 (12)
C7	0.0558 (16)	0.0582 (16)	0.0542 (16)	0.0055 (13)	0.0029 (13)	−0.0026 (13)
C8	0.0491 (15)	0.0538 (16)	0.0528 (16)	−0.0022 (12)	0.0035 (12)	0.0057 (13)
C9	0.0431 (14)	0.0415 (14)	0.0601 (15)	0.0028 (11)	−0.0010 (12)	−0.0026 (12)
C10	0.0593 (17)	0.0488 (16)	0.0701 (17)	−0.0025 (13)	0.0002 (14)	0.0051 (13)
C11	0.0580 (17)	0.0444 (15)	0.0845 (19)	−0.0060 (13)	0.0023 (15)	−0.0043 (14)
C12	0.0580 (17)	0.0526 (16)	0.0785 (18)	0.0024 (13)	0.0012 (15)	−0.0182 (15)
C13	0.0638 (17)	0.0558 (16)	0.0628 (17)	0.0054 (14)	0.0012 (14)	−0.0082 (14)
C14	0.0549 (15)	0.0440 (15)	0.0595 (16)	0.0041 (12)	0.0027 (13)	−0.0022 (12)
C15	0.0514 (14)	0.0491 (15)	0.0505 (14)	−0.0032 (12)	0.0020 (11)	0.0032 (12)
C16	0.0616 (16)	0.0541 (16)	0.0554 (16)	−0.0025 (13)	0.0011 (13)	0.0052 (13)
C17	0.0693 (18)	0.0611 (18)	0.0687 (18)	0.0042 (15)	−0.0066 (14)	0.0106 (15)
C18	0.0663 (17)	0.0719 (19)	0.089 (2)	0.0109 (15)	0.0018 (15)	0.0032 (17)
C19	0.0621 (17)	0.0722 (19)	0.0636 (17)	0.0075 (15)	0.0114 (14)	0.0130 (15)
C20	0.0684 (19)	0.085 (2)	0.0787 (19)	0.0111 (16)	0.0192 (16)	0.0080 (17)
C21	0.106 (3)	0.121 (3)	0.123 (3)	0.024 (3)	0.004 (2)	0.006 (3)
C22	0.164 (4)	0.140 (4)	0.150 (4)	0.008 (3)	0.005 (3)	0.021 (3)
C23	0.090 (3)	0.113 (3)	0.119 (3)	0.024 (2)	0.009 (2)	−0.002 (3)
C24	0.114 (4)	0.133 (4)	0.134 (4)	0.001 (3)	0.012 (3)	0.001 (3)
C21'	0.112 (3)	0.119 (3)	0.123 (3)	0.022 (3)	0.003 (3)	0.013 (3)
C22'	0.153 (5)	0.135 (4)	0.149 (5)	0.003 (4)	0.008 (4)	0.005 (3)
C23'	0.094 (3)	0.114 (3)	0.116 (3)	0.019 (3)	0.013 (3)	−0.001 (3)
C24'	0.123 (4)	0.130 (4)	0.130 (5)	0.000 (3)	0.013 (4)	−0.002 (4)
N1	0.0858 (18)	0.116 (2)	0.121 (2)	0.0296 (16)	0.0086 (16)	0.0113 (17)
N2	0.0629 (16)	0.0440 (14)	0.0571 (15)	−0.0043 (11)	−0.0099 (12)	0.0060 (11)
N3	0.0510 (14)	0.0407 (14)	0.0578 (15)	−0.0016 (11)	−0.0027 (11)	0.0016 (11)
N4	0.0717 (19)	0.0666 (19)	0.0706 (19)	−0.0078 (14)	0.0057 (14)	−0.0201 (15)

Geometric parameters (Å, º) top

C1—N4	1.341 (4)	C17—H17	0.9300
C1—C2	1.377 (5)	C18—N1	1.378 (5)
C1—C6	1.461 (4)	C18—C20	1.394 (5)
C2—C3	1.370 (5)	C19—C20	1.377 (5)
C2—H2	0.9300	C19—H19	0.9300
C3—C4	1.366 (6)	C20—H20	0.9300
C3—H3	0.9300	C21—C22	1.429 (12)
C4—C5	1.365 (6)	C21—N1	1.506 (9)
C4—H4	0.9300	C21—H21A	0.9700
C5—N4	1.345 (5)	C21—H21B	0.9700
C5—H5	0.9300	C22—H22A	0.9600
C6—N3	1.288 (4)	C22—H22B	0.9600
C6—C7	1.498 (4)	C22—H22C	0.9600
C7—C8	1.540 (4)	C23—C24	1.516 (12)
C7—H7A	0.9700	C23—N1	1.543 (10)
C7—H7B	0.9700	C23—H23A	0.9700
C8—N2	1.473 (4)	C23—H23B	0.9700
C8—C15	1.511 (4)	C24—H24A	0.9600
C8—H8	0.9800	C24—H24B	0.9600
C9—N2	1.383 (4)	C24—H24C	0.9600
C9—C14	1.390 (4)	C21'—C22'	1.390 (16)
C9—C10	1.398 (4)	C21'—N1	1.499 (12)
C10—C11	1.382 (5)	C21'—H21C	0.9700
C10—H10	0.9300	C21'—H21D	0.9700
C11—C12	1.372 (5)	C22'—H22D	0.9600
C11—H11	0.9300	C22'—H22E	0.9600
C12—C13	1.374 (5)	C22'—H22F	0.9600
C12—H12	0.9300	C23'—N1	1.470 (14)
C13—C14	1.386 (4)	C23'—C24'	1.498 (17)
C13—H13	0.9300	C23'—H23C	0.9700
C14—H14	0.9300	C23'—H23D	0.9700
C15—C16	1.381 (4)	C24'—H24D	0.9600
C15—C19	1.383 (4)	C24'—H24E	0.9600
C16—C17	1.375 (5)	C24'—H24F	0.9600
C16—H16	0.9300	N2—N3	1.371 (3)
C17—C18	1.398 (5)

N4—C1—C2	122.6 (3)	N1—C18—C17	122.8 (4)
N4—C1—C6	115.2 (3)	C20—C18—C17	116.1 (3)
C2—C1—C6	122.1 (3)	C20—C19—C15	121.7 (3)
C3—C2—C1	119.4 (3)	C20—C19—H19	119.1
C3—C2—H2	120.3	C15—C19—H19	119.1
C1—C2—H2	120.3	C19—C20—C18	121.7 (3)
C4—C3—C2	119.4 (4)	C19—C20—H20	119.2
C4—C3—H3	120.3	C18—C20—H20	119.2
C2—C3—H3	120.3	C22—C21—N1	112.9 (8)
C5—C4—C3	117.5 (4)	C22—C21—H21A	109.0
C5—C4—H4	121.2	N1—C21—H21A	109.0
C3—C4—H4	121.2	C22—C21—H21B	109.0
N4—C5—C4	125.2 (4)	N1—C21—H21B	109.0
N4—C5—H5	117.4	H21A—C21—H21B	107.8
C4—C5—H5	117.4	C24—C23—N1	111.0 (7)
N3—C6—C1	121.4 (3)	C24—C23—H23A	109.4
N3—C6—C7	113.1 (3)	N1—C23—H23A	109.4
C1—C6—C7	125.4 (3)	C24—C23—H23B	109.4
C6—C7—C8	102.4 (2)	N1—C23—H23B	109.4
C6—C7—H7A	111.3	H23A—C23—H23B	108.0
C8—C7—H7A	111.3	C22'—C21'—N1	124.9 (14)
C6—C7—H7B	111.3	C22'—C21'—H21C	106.1
C8—C7—H7B	111.3	N1—C21'—H21C	106.1
H7A—C7—H7B	109.2	C22'—C21'—H21D	106.1
N2—C8—C15	112.8 (2)	N1—C21'—H21D	106.1
N2—C8—C7	100.6 (2)	H21C—C21'—H21D	106.3
C15—C8—C7	113.4 (2)	C21'—C22'—H22D	109.5
N2—C8—H8	109.9	C21'—C22'—H22E	109.5
C15—C8—H8	109.9	H22D—C22'—H22E	109.5
C7—C8—H8	109.9	C21'—C22'—H22F	109.5
N2—C9—C14	120.8 (3)	H22D—C22'—H22F	109.5
N2—C9—C10	120.6 (3)	H22E—C22'—H22F	109.5
C14—C9—C10	118.6 (3)	N1—C23'—C24'	115.7 (12)
C11—C10—C9	119.7 (3)	N1—C23'—H23C	108.4
C11—C10—H10	120.1	C24'—C23'—H23C	108.4
C9—C10—H10	120.1	N1—C23'—H23D	108.4
C12—C11—C10	121.5 (3)	C24'—C23'—H23D	108.4
C12—C11—H11	119.2	H23C—C23'—H23D	107.4
C10—C11—H11	119.2	C23'—C24'—H24D	109.5
C11—C12—C13	118.8 (3)	C23'—C24'—H24E	109.5
C11—C12—H12	120.6	H24D—C24'—H24E	109.5
C13—C12—H12	120.6	C23'—C24'—H24F	109.5
C12—C13—C14	121.0 (3)	H24D—C24'—H24F	109.5
C12—C13—H13	119.5	H24E—C24'—H24F	109.5
C14—C13—H13	119.5	C18—N1—C23'	124.9 (8)
C13—C14—C9	120.2 (3)	C18—N1—C21'	127.5 (6)
C13—C14—H14	119.9	C23'—N1—C21'	107.5 (9)
C9—C14—H14	119.9	C18—N1—C21	120.2 (5)
C16—C15—C19	117.1 (3)	C23'—N1—C21	102.2 (8)
C16—C15—C8	121.0 (3)	C18—N1—C23	118.7 (5)
C19—C15—C8	121.7 (3)	C21'—N1—C23	110.8 (7)
C17—C16—C15	121.6 (3)	C21—N1—C23	118.0 (6)
C17—C16—H16	119.2	N3—N2—C9	120.2 (2)
C15—C16—H16	119.2	N3—N2—C8	112.7 (2)
C16—C17—C18	121.8 (3)	C9—N2—C8	126.6 (2)
C16—C17—H17	119.1	C6—N3—N2	108.8 (2)
C18—C17—H17	119.1	C1—N4—C5	115.8 (3)
N1—C18—C20	121.2 (4)

N4—C1—C2—C3	2.0 (5)	C20—C18—N1—C21'	158.4 (10)
C6—C1—C2—C3	−178.6 (3)	C17—C18—N1—C21'	−21.0 (11)
C1—C2—C3—C4	−1.1 (6)	C20—C18—N1—C21	−160.3 (6)
C2—C3—C4—C5	0.1 (6)	C17—C18—N1—C21	20.3 (8)
C3—C4—C5—N4	0.2 (7)	C20—C18—N1—C23	−0.5 (7)
N4—C1—C6—N3	−177.9 (3)	C17—C18—N1—C23	−179.9 (5)
C2—C1—C6—N3	2.7 (5)	C24'—C23'—N1—C18	−69.5 (17)
N4—C1—C6—C7	−1.5 (4)	C24'—C23'—N1—C21'	107.3 (16)
C2—C1—C6—C7	179.1 (3)	C24'—C23'—N1—C21	71.6 (16)
N3—C6—C7—C8	−10.6 (3)	C24'—C23'—N1—C23	−150 (4)
C1—C6—C7—C8	172.7 (3)	C22'—C21'—N1—C18	−93.3 (15)
C6—C7—C8—N2	14.0 (3)	C22'—C21'—N1—C23'	90.1 (16)
C6—C7—C8—C15	−106.7 (3)	C22'—C21'—N1—C21	176 (2)
N2—C9—C10—C11	−176.6 (3)	C22'—C21'—N1—C23	67.0 (16)
C14—C9—C10—C11	2.8 (5)	C22—C21—N1—C18	−110.5 (8)
C9—C10—C11—C12	−1.5 (5)	C22—C21—N1—C23'	106.1 (10)
C10—C11—C12—C13	−0.3 (5)	C22—C21—N1—C21'	2.9 (10)
C11—C12—C13—C14	0.8 (5)	C22—C21—N1—C23	89.6 (9)
C12—C13—C14—C9	0.5 (5)	C24—C23—N1—C18	−77.2 (8)
N2—C9—C14—C13	177.0 (3)	C24—C23—N1—C23'	35 (2)
C10—C9—C14—C13	−2.4 (4)	C24—C23—N1—C21'	120.6 (10)
N2—C8—C15—C16	157.4 (3)	C24—C23—N1—C21	83.1 (9)
C7—C8—C15—C16	−89.1 (3)	C14—C9—N2—N3	−3.0 (4)
N2—C8—C15—C19	−27.6 (4)	C10—C9—N2—N3	176.4 (3)
C7—C8—C15—C19	85.9 (4)	C14—C9—N2—C8	167.8 (3)
C19—C15—C16—C17	−1.5 (5)	C10—C9—N2—C8	−12.8 (5)
C8—C15—C16—C17	173.7 (3)	C15—C8—N2—N3	106.4 (3)
C15—C16—C17—C18	−0.3 (5)	C7—C8—N2—N3	−14.7 (3)
C16—C17—C18—N1	−178.7 (4)	C15—C8—N2—C9	−65.0 (4)
C16—C17—C18—C20	1.9 (6)	C7—C8—N2—C9	173.9 (3)
C16—C15—C19—C20	1.6 (5)	C1—C6—N3—N2	178.5 (3)
C8—C15—C19—C20	−173.6 (3)	C7—C6—N3—N2	1.7 (3)
C15—C19—C20—C18	0.1 (6)	C9—N2—N3—C6	−179.1 (3)
N1—C18—C20—C19	178.8 (4)	C8—N2—N3—C6	8.9 (3)
C17—C18—C20—C19	−1.8 (6)	C2—C1—N4—C5	−1.7 (5)
C20—C18—N1—C23'	−25.5 (10)	C6—C1—N4—C5	178.9 (3)
C17—C18—N1—C23'	155.1 (9)	C4—C5—N4—C1	0.6 (6)

Experimental details

Crystal data
Chemical formula	C₂₄H₂₆N₄
M_r	370.49
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	14.902 (5), 11.314 (5), 12.479 (5)
β (°)	94.644 (5)
V (Å³)	2097.1 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.979, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	14365, 3678, 2511
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.241, 1.06
No. of reflections	3678
No. of parameters	294
No. of restraints	507
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.52

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by grants from the National Natural Science Foundation of China (grant No. 21271004) and the Natural Science Foundation of Anhui Province (grant No. 1208085MB22).

References

Bruker (2000). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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