organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

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[Chen, Y., Li, D.-C., Zhu, Y. & Wang, D.-Q. (2008). Acta Cryst. E64, o1629.]); Dong et al. (2010[Dong, B.-L., Wang, M.-L. & Li, Y.-H. (2010). Acta Cryst. E66, o2786.]); Guo et al. (2010[Guo, H.-M., Huang, B.-Y., Qin, X., Zou, H.-Z. & Jian, F.-F. (2010). Acta Cryst. E66, o1587.]); Liu et al. (2010[Liu, W.-Y., Xie, Y.-S., Wang, B.-S. & Zhao, B.-X. (2010). Acta Cryst. E66, m1275.]).

[Scheme 1]

Experimental

Crystal data
  • C24H26N4

  • Mr = 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[Bruker (2000). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.979, Tmax = 0.986

  • 14365 measured reflections

  • 3678 independent reflections

  • 2511 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.52 e Å−3

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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).

Refinement top

All hydrogen atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.93 Å and Uiso(H) = 1.2 Ueq. The ethyl groups of the N,N-diethylamino group are disordered over two positions. Restraints were imposed on C-C and C-N distances and displacement parameters in these groups.

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
[Figure 1] 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
C24H26N4F(000) = 792
Mr = 370.49Dx = 1.173 Mg m3
Monoclinic, P21/cMelting point: 391 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71069 Å
a = 14.902 (5) ÅCell parameters from 3174 reflections
b = 11.314 (5) Åθ = 2.4–23.1°
c = 12.479 (5) ŵ = 0.07 mm1
β = 94.644 (5)°T = 296 K
V = 2097.1 (14) Å3Block, yellow
Z = 40.30 × 0.20 × 0.20 mm
Data collection top
Bruker SMART APEX CCD
diffractometer
3678 independent reflections
Radiation source: fine-focus sealed tube2511 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ϕ and ω scansθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1717
Tmin = 0.979, Tmax = 0.986k = 1313
14365 measured reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.073Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.241H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.1447P)2 + 0.5666P]
where P = (Fo2 + 2Fc2)/3
3678 reflections(Δ/σ)max = 0.002
294 parametersΔρmax = 0.37 e Å3
507 restraintsΔρmin = 0.52 e Å3
Crystal data top
C24H26N4V = 2097.1 (14) Å3
Mr = 370.49Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.902 (5) ŵ = 0.07 mm1
b = 11.314 (5) ÅT = 296 K
c = 12.479 (5) Å0.30 × 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)
Tmin = 0.979, Tmax = 0.986Rint = 0.038
14365 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.073507 restraints
wR(F2) = 0.241H-atom parameters constrained
S = 1.06Δρmax = 0.37 e Å3
3678 reflectionsΔρmin = 0.52 e Å3
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
xyzUiso*/UeqOcc. (<1)
C10.3073 (2)0.2820 (3)0.4677 (3)0.0539 (7)
C20.3140 (2)0.3449 (3)0.5624 (3)0.0662 (9)
H20.33160.30740.62710.079*
C30.2946 (3)0.4632 (3)0.5606 (4)0.0815 (10)
H30.30000.50710.62390.098*
C40.2674 (3)0.5163 (4)0.4651 (4)0.0864 (11)
H40.25380.59650.46160.104*
C50.2611 (3)0.4473 (4)0.3752 (4)0.0821 (11)
H50.24230.48350.31030.099*
C60.32889 (19)0.1562 (3)0.4637 (2)0.0504 (7)
C70.3245 (2)0.0819 (3)0.3641 (2)0.0561 (8)
H7A0.26590.08760.32450.067*
H7B0.37060.10470.31750.067*
C80.3415 (2)0.0433 (3)0.4096 (2)0.0519 (7)
H80.38880.08220.37230.062*
C90.40911 (18)0.0948 (2)0.5983 (2)0.0485 (7)
C100.4309 (2)0.2102 (3)0.5699 (3)0.0597 (8)
H100.41980.23570.49920.072*
C110.4691 (2)0.2863 (3)0.6473 (3)0.0625 (8)
H110.48480.36230.62750.075*
C120.4846 (2)0.2523 (3)0.7527 (3)0.0633 (8)
H120.51060.30430.80390.076*
C130.4608 (2)0.1400 (3)0.7814 (3)0.0610 (8)
H130.47030.11640.85280.073*
C140.4230 (2)0.0613 (3)0.7055 (2)0.0529 (7)
H140.40690.01420.72640.064*
C150.2580 (2)0.1196 (3)0.4035 (2)0.0504 (7)
C160.2344 (2)0.1879 (3)0.3139 (3)0.0572 (8)
H160.27360.19270.25970.069*
C170.1544 (2)0.2488 (3)0.3028 (3)0.0670 (9)
H170.14100.29420.24150.080*
C180.0926 (3)0.2446 (3)0.3813 (3)0.0760 (9)
C190.1985 (2)0.1174 (3)0.4831 (3)0.0656 (9)
H190.21320.07380.54520.079*
C200.1182 (3)0.1780 (4)0.4727 (3)0.0767 (10)
H200.08010.17440.52800.092*
C210.0287 (6)0.3410 (9)0.2615 (7)0.1169 (19)0.624 (8)
H21A0.00490.30450.20690.140*0.624 (8)
H21B0.09030.31280.25140.140*0.624 (8)
C220.0282 (8)0.4663 (10)0.2471 (10)0.151 (3)0.624 (8)
H22A0.06910.50220.29310.227*0.624 (8)
H22B0.04650.48490.17350.227*0.624 (8)
H22C0.03150.49610.26510.227*0.624 (8)
C230.0521 (6)0.2931 (9)0.4622 (8)0.1072 (18)0.624 (8)
H23A0.01750.30150.53100.129*0.624 (8)
H23B0.09610.35640.45560.129*0.624 (8)
C240.1004 (7)0.1750 (9)0.4583 (10)0.127 (2)0.624 (8)
H24A0.14620.17480.39950.190*0.624 (8)
H24B0.12770.16270.52450.190*0.624 (8)
H24C0.05800.11290.44830.190*0.624 (8)
C21'0.0141 (8)0.4066 (13)0.2996 (14)0.118 (2)0.376 (8)
H21C0.02050.39860.23730.142*0.376 (8)
H21D0.07660.39470.27390.142*0.376 (8)
C22'0.0068 (15)0.5244 (13)0.3306 (17)0.146 (3)0.376 (8)
H22D0.00770.57360.26790.219*0.376 (8)
H22E0.04880.53600.37390.219*0.376 (8)
H22F0.05630.54490.37150.219*0.376 (8)
C23'0.0689 (11)0.2690 (15)0.4247 (14)0.108 (2)0.376 (8)
H23C0.11250.33260.41580.129*0.376 (8)
H23D0.05180.26120.50100.129*0.376 (8)
C24'0.1138 (11)0.1567 (14)0.3859 (17)0.128 (3)0.376 (8)
H24D0.15290.17250.32260.191*0.376 (8)
H24E0.14830.12530.44100.191*0.376 (8)
H24F0.06890.10020.36920.191*0.376 (8)
N10.0113 (3)0.3032 (4)0.3708 (4)0.1077 (11)
N20.37522 (17)0.0154 (2)0.5210 (2)0.0555 (7)
N30.35871 (16)0.0994 (2)0.5487 (2)0.0502 (7)
N40.2797 (2)0.3311 (3)0.3729 (2)0.0696 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0467 (15)0.0507 (15)0.0640 (17)0.0005 (12)0.0025 (13)0.0102 (13)
C20.0719 (19)0.0515 (16)0.0733 (18)0.0062 (14)0.0061 (15)0.0017 (14)
C30.093 (2)0.0560 (18)0.093 (2)0.0094 (17)0.0055 (19)0.0011 (16)
C40.091 (2)0.060 (2)0.107 (2)0.0093 (18)0.000 (2)0.0174 (17)
C50.085 (2)0.070 (2)0.091 (2)0.0079 (19)0.0039 (19)0.0321 (18)
C60.0451 (14)0.0499 (15)0.0558 (16)0.0017 (12)0.0025 (12)0.0043 (12)
C70.0558 (16)0.0582 (16)0.0542 (16)0.0055 (13)0.0029 (13)0.0026 (13)
C80.0491 (15)0.0538 (16)0.0528 (16)0.0022 (12)0.0035 (12)0.0057 (13)
C90.0431 (14)0.0415 (14)0.0601 (15)0.0028 (11)0.0010 (12)0.0026 (12)
C100.0593 (17)0.0488 (16)0.0701 (17)0.0025 (13)0.0002 (14)0.0051 (13)
C110.0580 (17)0.0444 (15)0.0845 (19)0.0060 (13)0.0023 (15)0.0043 (14)
C120.0580 (17)0.0526 (16)0.0785 (18)0.0024 (13)0.0012 (15)0.0182 (15)
C130.0638 (17)0.0558 (16)0.0628 (17)0.0054 (14)0.0012 (14)0.0082 (14)
C140.0549 (15)0.0440 (15)0.0595 (16)0.0041 (12)0.0027 (13)0.0022 (12)
C150.0514 (14)0.0491 (15)0.0505 (14)0.0032 (12)0.0020 (11)0.0032 (12)
C160.0616 (16)0.0541 (16)0.0554 (16)0.0025 (13)0.0011 (13)0.0052 (13)
C170.0693 (18)0.0611 (18)0.0687 (18)0.0042 (15)0.0066 (14)0.0106 (15)
C180.0663 (17)0.0719 (19)0.089 (2)0.0109 (15)0.0018 (15)0.0032 (17)
C190.0621 (17)0.0722 (19)0.0636 (17)0.0075 (15)0.0114 (14)0.0130 (15)
C200.0684 (19)0.085 (2)0.0787 (19)0.0111 (16)0.0192 (16)0.0080 (17)
C210.106 (3)0.121 (3)0.123 (3)0.024 (3)0.004 (2)0.006 (3)
C220.164 (4)0.140 (4)0.150 (4)0.008 (3)0.005 (3)0.021 (3)
C230.090 (3)0.113 (3)0.119 (3)0.024 (2)0.009 (2)0.002 (3)
C240.114 (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)
N10.0858 (18)0.116 (2)0.121 (2)0.0296 (16)0.0086 (16)0.0113 (17)
N20.0629 (16)0.0440 (14)0.0571 (15)0.0043 (11)0.0099 (12)0.0060 (11)
N30.0510 (14)0.0407 (14)0.0578 (15)0.0016 (11)0.0027 (11)0.0016 (11)
N40.0717 (19)0.0666 (19)0.0706 (19)0.0078 (14)0.0057 (14)0.0201 (15)
Geometric parameters (Å, º) top
C1—N41.341 (4)C17—H170.9300
C1—C21.377 (5)C18—N11.378 (5)
C1—C61.461 (4)C18—C201.394 (5)
C2—C31.370 (5)C19—C201.377 (5)
C2—H20.9300C19—H190.9300
C3—C41.366 (6)C20—H200.9300
C3—H30.9300C21—C221.429 (12)
C4—C51.365 (6)C21—N11.506 (9)
C4—H40.9300C21—H21A0.9700
C5—N41.345 (5)C21—H21B0.9700
C5—H50.9300C22—H22A0.9600
C6—N31.288 (4)C22—H22B0.9600
C6—C71.498 (4)C22—H22C0.9600
C7—C81.540 (4)C23—C241.516 (12)
C7—H7A0.9700C23—N11.543 (10)
C7—H7B0.9700C23—H23A0.9700
C8—N21.473 (4)C23—H23B0.9700
C8—C151.511 (4)C24—H24A0.9600
C8—H80.9800C24—H24B0.9600
C9—N21.383 (4)C24—H24C0.9600
C9—C141.390 (4)C21'—C22'1.390 (16)
C9—C101.398 (4)C21'—N11.499 (12)
C10—C111.382 (5)C21'—H21C0.9700
C10—H100.9300C21'—H21D0.9700
C11—C121.372 (5)C22'—H22D0.9600
C11—H110.9300C22'—H22E0.9600
C12—C131.374 (5)C22'—H22F0.9600
C12—H120.9300C23'—N11.470 (14)
C13—C141.386 (4)C23'—C24'1.498 (17)
C13—H130.9300C23'—H23C0.9700
C14—H140.9300C23'—H23D0.9700
C15—C161.381 (4)C24'—H24D0.9600
C15—C191.383 (4)C24'—H24E0.9600
C16—C171.375 (5)C24'—H24F0.9600
C16—H160.9300N2—N31.371 (3)
C17—C181.398 (5)
N4—C1—C2122.6 (3)N1—C18—C17122.8 (4)
N4—C1—C6115.2 (3)C20—C18—C17116.1 (3)
C2—C1—C6122.1 (3)C20—C19—C15121.7 (3)
C3—C2—C1119.4 (3)C20—C19—H19119.1
C3—C2—H2120.3C15—C19—H19119.1
C1—C2—H2120.3C19—C20—C18121.7 (3)
C4—C3—C2119.4 (4)C19—C20—H20119.2
C4—C3—H3120.3C18—C20—H20119.2
C2—C3—H3120.3C22—C21—N1112.9 (8)
C5—C4—C3117.5 (4)C22—C21—H21A109.0
C5—C4—H4121.2N1—C21—H21A109.0
C3—C4—H4121.2C22—C21—H21B109.0
N4—C5—C4125.2 (4)N1—C21—H21B109.0
N4—C5—H5117.4H21A—C21—H21B107.8
C4—C5—H5117.4C24—C23—N1111.0 (7)
N3—C6—C1121.4 (3)C24—C23—H23A109.4
N3—C6—C7113.1 (3)N1—C23—H23A109.4
C1—C6—C7125.4 (3)C24—C23—H23B109.4
C6—C7—C8102.4 (2)N1—C23—H23B109.4
C6—C7—H7A111.3H23A—C23—H23B108.0
C8—C7—H7A111.3C22'—C21'—N1124.9 (14)
C6—C7—H7B111.3C22'—C21'—H21C106.1
C8—C7—H7B111.3N1—C21'—H21C106.1
H7A—C7—H7B109.2C22'—C21'—H21D106.1
N2—C8—C15112.8 (2)N1—C21'—H21D106.1
N2—C8—C7100.6 (2)H21C—C21'—H21D106.3
C15—C8—C7113.4 (2)C21'—C22'—H22D109.5
N2—C8—H8109.9C21'—C22'—H22E109.5
C15—C8—H8109.9H22D—C22'—H22E109.5
C7—C8—H8109.9C21'—C22'—H22F109.5
N2—C9—C14120.8 (3)H22D—C22'—H22F109.5
N2—C9—C10120.6 (3)H22E—C22'—H22F109.5
C14—C9—C10118.6 (3)N1—C23'—C24'115.7 (12)
C11—C10—C9119.7 (3)N1—C23'—H23C108.4
C11—C10—H10120.1C24'—C23'—H23C108.4
C9—C10—H10120.1N1—C23'—H23D108.4
C12—C11—C10121.5 (3)C24'—C23'—H23D108.4
C12—C11—H11119.2H23C—C23'—H23D107.4
C10—C11—H11119.2C23'—C24'—H24D109.5
C11—C12—C13118.8 (3)C23'—C24'—H24E109.5
C11—C12—H12120.6H24D—C24'—H24E109.5
C13—C12—H12120.6C23'—C24'—H24F109.5
C12—C13—C14121.0 (3)H24D—C24'—H24F109.5
C12—C13—H13119.5H24E—C24'—H24F109.5
C14—C13—H13119.5C18—N1—C23'124.9 (8)
C13—C14—C9120.2 (3)C18—N1—C21'127.5 (6)
C13—C14—H14119.9C23'—N1—C21'107.5 (9)
C9—C14—H14119.9C18—N1—C21120.2 (5)
C16—C15—C19117.1 (3)C23'—N1—C21102.2 (8)
C16—C15—C8121.0 (3)C18—N1—C23118.7 (5)
C19—C15—C8121.7 (3)C21'—N1—C23110.8 (7)
C17—C16—C15121.6 (3)C21—N1—C23118.0 (6)
C17—C16—H16119.2N3—N2—C9120.2 (2)
C15—C16—H16119.2N3—N2—C8112.7 (2)
C16—C17—C18121.8 (3)C9—N2—C8126.6 (2)
C16—C17—H17119.1C6—N3—N2108.8 (2)
C18—C17—H17119.1C1—N4—C5115.8 (3)
N1—C18—C20121.2 (4)
N4—C1—C2—C32.0 (5)C20—C18—N1—C21'158.4 (10)
C6—C1—C2—C3178.6 (3)C17—C18—N1—C21'21.0 (11)
C1—C2—C3—C41.1 (6)C20—C18—N1—C21160.3 (6)
C2—C3—C4—C50.1 (6)C17—C18—N1—C2120.3 (8)
C3—C4—C5—N40.2 (7)C20—C18—N1—C230.5 (7)
N4—C1—C6—N3177.9 (3)C17—C18—N1—C23179.9 (5)
C2—C1—C6—N32.7 (5)C24'—C23'—N1—C1869.5 (17)
N4—C1—C6—C71.5 (4)C24'—C23'—N1—C21'107.3 (16)
C2—C1—C6—C7179.1 (3)C24'—C23'—N1—C2171.6 (16)
N3—C6—C7—C810.6 (3)C24'—C23'—N1—C23150 (4)
C1—C6—C7—C8172.7 (3)C22'—C21'—N1—C1893.3 (15)
C6—C7—C8—N214.0 (3)C22'—C21'—N1—C23'90.1 (16)
C6—C7—C8—C15106.7 (3)C22'—C21'—N1—C21176 (2)
N2—C9—C10—C11176.6 (3)C22'—C21'—N1—C2367.0 (16)
C14—C9—C10—C112.8 (5)C22—C21—N1—C18110.5 (8)
C9—C10—C11—C121.5 (5)C22—C21—N1—C23'106.1 (10)
C10—C11—C12—C130.3 (5)C22—C21—N1—C21'2.9 (10)
C11—C12—C13—C140.8 (5)C22—C21—N1—C2389.6 (9)
C12—C13—C14—C90.5 (5)C24—C23—N1—C1877.2 (8)
N2—C9—C14—C13177.0 (3)C24—C23—N1—C23'35 (2)
C10—C9—C14—C132.4 (4)C24—C23—N1—C21'120.6 (10)
N2—C8—C15—C16157.4 (3)C24—C23—N1—C2183.1 (9)
C7—C8—C15—C1689.1 (3)C14—C9—N2—N33.0 (4)
N2—C8—C15—C1927.6 (4)C10—C9—N2—N3176.4 (3)
C7—C8—C15—C1985.9 (4)C14—C9—N2—C8167.8 (3)
C19—C15—C16—C171.5 (5)C10—C9—N2—C812.8 (5)
C8—C15—C16—C17173.7 (3)C15—C8—N2—N3106.4 (3)
C15—C16—C17—C180.3 (5)C7—C8—N2—N314.7 (3)
C16—C17—C18—N1178.7 (4)C15—C8—N2—C965.0 (4)
C16—C17—C18—C201.9 (6)C7—C8—N2—C9173.9 (3)
C16—C15—C19—C201.6 (5)C1—C6—N3—N2178.5 (3)
C8—C15—C19—C20173.6 (3)C7—C6—N3—N21.7 (3)
C15—C19—C20—C180.1 (6)C9—N2—N3—C6179.1 (3)
N1—C18—C20—C19178.8 (4)C8—N2—N3—C68.9 (3)
C17—C18—C20—C191.8 (6)C2—C1—N4—C51.7 (5)
C20—C18—N1—C23'25.5 (10)C6—C1—N4—C5178.9 (3)
C17—C18—N1—C23'155.1 (9)C4—C5—N4—C10.6 (6)

Experimental details

Crystal data
Chemical formulaC24H26N4
Mr370.49
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)14.902 (5), 11.314 (5), 12.479 (5)
β (°) 94.644 (5)
V3)2097.1 (14)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.979, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
14365, 3678, 2511
Rint0.038
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.073, 0.241, 1.06
No. of reflections3678
No. of parameters294
No. of restraints507
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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

First citationBruker (2000). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationBruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationChen, Y., Li, D.-C., Zhu, Y. & Wang, D.-Q. (2008). Acta Cryst. E64, o1629.  Web of Science CSD CrossRef IUCr Journals
First citationDong, B.-L., Wang, M.-L. & Li, Y.-H. (2010). Acta Cryst. E66, o2786.  Web of Science CSD CrossRef IUCr Journals
First citationGuo, H.-M., Huang, B.-Y., Qin, X., Zou, H.-Z. & Jian, F.-F. (2010). Acta Cryst. E66, o1587.  Web of Science CSD CrossRef IUCr Journals
First citationLiu, W.-Y., Xie, Y.-S., Wang, B.-S. & Zhao, B.-X. (2010). Acta Cryst. E66, m1275.  Web of Science CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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