supplementary materials


zs2260 scheme

Acta Cryst. (2013). E69, o1006    [ doi:10.1107/S160053681301444X ]

4-(4,5-Diphenyl-1H-imidazol-2-yl)-N,N-dimethylaniline

M. Prabhuswamy, S. Viveka, S. Madan Kumar, G. K. Nagaraja and N. K. Lokanath

Abstract top

The asymmetric unit of the title compound, C23H21N3, consists of two symmetry-independent and conformationally different molecules [the comparable dihedral angles between the imidazole ring and the three benzene rings being 38.5 (2)/61.5 (3)/3.37 (17) and 45.8 (2)/36.01 (19)/46.94 (17)°]. In the crystal, intermolecular imidazole N-H...N hydrogen-bonding interactions give a one-dimensional chain extending along [101].

Comment top

As a continuation of our studies on the molecular structures of some of the biologically active imidazole derivatives (Ucucu, et al., 2001), we have synthesized the title compound, the substituted imidazole C23H21N3 and the crystal structure is reported herein. The asymmetric unit of this compound consists of two symmetry-independent and conformationally different molecules, A and B (Fig. 1 & Fig. 2). The two molecules depart significantly from planarity. In molecule A, the imidazole ring forms dihedral angles of 38.5 (2), 61.5 (3) and 3.37 (17)° with phenyl rings C6A/C7A/C8A/C9A/C10A/C11A, C12A/C13A/C14A/C15A/C16A/C17A and the dimethylaniline substituted phenyl ring C18A/C19A/C20A/C21A/C22A/C23A respectively. These values compare with 45.8 (2), 36.01 (19) and 46.94 (17)° for the corresponding angles in molecule B. The overall geometry of the title compound is similar to that of 4-(1-allyl-4,5-diphenyl-1H-imidazol-2-yl)-N,N- dimethylaniline (Akkurt et al., 2013)

In the crystal, the A and B molecules are connected by imidazole N—H···N hydrogen bonds (Table 1) both within the asymmetric unit (N1A-H···N3B) and between the unit (N1B-H···N3B)i, giving chains extending along [1 0 1] (Fig. 3). The crystal structure is also stabilized with short contacts of the type C25B—H25B···Cg6 [x -1/2, y + 3/2, z +1/2] with a C···Cg distance of 3.726 (10) Å (C—H···Cg angle, 134°) (where Cg6 is C6B/C7B/C8B/C9B/C10B/C11B).

Related literature top

For background on imidazoles, see: Ucucu et al. (2001). For similar structures, see: Yanover & Kaftory (2009); Akkurt et al. (2013); Prabhuswamy et al. (2013).

Experimental top

Benzil (1 mmol), N,N-dimethyl benzaldehyde (1 mmol), and ammonium acetate (2 mmol) were dissolved in boiling glacial acetic acid and refluxed for 5–6 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-water. The title compound obtained was recrystallized from DMF.

Refinement top

The imidazole N-bound H-atoms (H1B and H3A) were located in a difference Fourier map but were allowed to ride in the refinement with Uiso = 1.2Ueq(N). All other hydrogen atoms were positioned geometrically and also refined using a riding model with C—H = 0.93–0.96 Å and Uiso(methyl H) = 1.5 Ueq(C) and Uiso(H) = 1.2 Ueq(C) for other hydrogen atoms.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. Molecular conformation and atom numbering scheme for molecule A of the title compound showing 30% probability ellipsoids.
[Figure 2] Fig. 2. Molecular conformation and atom numbering scheme for molecule B of the title compound showing 30% probability ellipsoids.
[Figure 3] Fig. 3. The packing of molecules of the title compound when viewed down the crystallographic b-axis.
4-(4,5-Diphenyl-1H-imidazol-2-yl)-N,N-dimethylaniline top
Crystal data top
C23H21N3F(000) = 1440
Mr = 339.43Dx = 1.181 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3349 reflections
a = 15.228 (4) Åθ = 1.5–25.4°
b = 15.215 (4) ŵ = 0.07 mm1
c = 17.641 (4) ÅT = 296 K
β = 110.974 (4)°Block, white
V = 3816.5 (17) Å30.24 × 0.19 × 0.17 mm
Z = 8
Data collection top
Oxford Xcalibur Eos (Nova) CCD
diffractometer
Rint = 0.063
Radiation source: graphiteθmax = 25.4°, θmin = 1.5°
ω scansh = 1818
36558 measured reflectionsk = 1818
6983 independent reflectionsl = 2121
3921 reflections with I > 2σ(I)
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)] = 0.070Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0546P)2 + 1.5051P]
where P = (Fo2 + 2Fc2)/3
6983 reflections(Δ/σ)max < 0.001
475 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C23H21N3V = 3816.5 (17) Å3
Mr = 339.43Z = 8
Monoclinic, P21/nMo Kα radiation
a = 15.228 (4) ŵ = 0.07 mm1
b = 15.215 (4) ÅT = 296 K
c = 17.641 (4) Å0.24 × 0.19 × 0.17 mm
β = 110.974 (4)°
Data collection top
Oxford Xcalibur Eos (Nova) CCD
diffractometer
3921 reflections with I > 2σ(I)
36558 measured reflectionsRint = 0.063
6983 independent reflectionsθmax = 25.4°
Refinement top
R[F2 > 2σ(F2)] = 0.070H-atom parameters constrained
wR(F2) = 0.175Δρmax = 0.22 e Å3
S = 1.02Δρmin = 0.17 e Å3
6983 reflectionsAbsolute structure: ?
475 parametersAbsolute structure parameter: ?
0 restraintsRogers parameter: ?
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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*/Ueq
N1A0.86183 (15)0.76491 (16)0.18460 (13)0.0584 (8)
N3A0.78361 (16)0.72591 (16)0.05759 (13)0.0602 (8)
N24A0.83099 (19)0.34428 (18)0.23863 (16)0.0807 (11)
C2A0.82417 (18)0.6976 (2)0.13534 (15)0.0553 (10)
C4A0.7950 (2)0.8155 (2)0.05703 (17)0.0673 (11)
C5A0.8443 (2)0.8388 (2)0.13560 (17)0.0649 (11)
C6A0.8763 (2)0.9259 (2)0.1700 (2)0.0701 (12)
C7A0.8746 (2)0.9490 (3)0.2452 (2)0.0911 (17)
C8A0.9042 (3)1.0308 (3)0.2780 (3)0.123 (2)
C9A0.9386 (4)1.0895 (3)0.2368 (4)0.132 (3)
C10A0.9427 (4)1.0679 (3)0.1633 (3)0.133 (2)
C11A0.9111 (3)0.9864 (3)0.1297 (2)0.1061 (18)
C12A0.7547 (3)0.8661 (2)0.0189 (2)0.0850 (12)
C13A0.7797 (4)0.8527 (3)0.0825 (2)0.147 (3)
C14A0.7401 (7)0.8992 (4)0.1535 (3)0.222 (5)
C15A0.6765 (7)0.9541 (5)0.1633 (4)0.212 (4)
C16A0.6477 (4)0.9767 (5)0.0979 (5)0.217 (4)
C17A0.6869 (3)0.9276 (4)0.0258 (4)0.170 (3)
C18A0.82588 (18)0.60609 (19)0.16014 (15)0.0536 (10)
C19A0.8725 (2)0.5815 (2)0.24015 (17)0.0759 (11)
C20A0.8746 (2)0.4964 (2)0.26631 (18)0.0757 (11)
C21A0.83009 (19)0.4297 (2)0.21340 (17)0.0596 (10)
C22A0.7824 (2)0.4538 (2)0.13234 (17)0.0646 (11)
C23A0.78093 (19)0.5392 (2)0.10748 (16)0.0597 (10)
C25A0.8782 (3)0.3207 (2)0.3227 (2)0.0947 (17)
C26A0.7788 (3)0.2772 (2)0.1834 (2)0.1125 (18)
N1B0.54844 (15)0.70966 (15)0.19536 (12)0.0547 (8)
N3B0.66562 (15)0.65014 (15)0.09518 (12)0.0539 (8)
N24B0.3533 (3)0.7156 (4)0.0775 (2)0.151 (2)
C2B0.58022 (19)0.68405 (18)0.11642 (15)0.0518 (9)
C4B0.68886 (19)0.65370 (18)0.16416 (15)0.0531 (10)
C5B0.61568 (19)0.68851 (18)0.22724 (15)0.0541 (10)
C6B0.5964 (2)0.6996 (2)0.31453 (16)0.0628 (10)
C7B0.5525 (2)0.7741 (2)0.35569 (18)0.0797 (14)
C8B0.5278 (3)0.7807 (3)0.4385 (2)0.1081 (18)
C9B0.5460 (4)0.7140 (4)0.4806 (2)0.134 (2)
C10B0.5898 (4)0.6390 (3)0.4418 (2)0.127 (2)
C11B0.6156 (3)0.6321 (3)0.35784 (19)0.0899 (15)
C12B0.7834 (2)0.6277 (2)0.16052 (16)0.0622 (10)
C13B0.8300 (2)0.5599 (2)0.11106 (19)0.0844 (14)
C14B0.9203 (3)0.5368 (3)0.1059 (2)0.1113 (19)
C15B0.9643 (3)0.5821 (5)0.1483 (3)0.129 (3)
C16B0.9190 (3)0.6502 (4)0.1965 (3)0.118 (2)
C17B0.8294 (3)0.6736 (3)0.2026 (2)0.0870 (14)
C18B0.52508 (19)0.6943 (2)0.06419 (15)0.0556 (10)
C19B0.4782 (2)0.7711 (3)0.06192 (19)0.0830 (14)
C20B0.4225 (3)0.7786 (3)0.0151 (2)0.1105 (19)
C21B0.4111 (3)0.7093 (4)0.0308 (2)0.101 (2)
C22B0.4597 (3)0.6344 (3)0.0302 (2)0.0988 (19)
C23B0.5161 (2)0.6276 (2)0.01595 (19)0.0789 (14)
C25B0.3008 (6)0.7926 (7)0.0707 (5)0.291 (7)
C26B0.3240 (5)0.6381 (6)0.1069 (4)0.213 (4)
H3A0.751100.684700.010400.091 (10)*
H7A0.853100.908700.274100.1090*
H8A0.900801.046100.327900.1480*
H9A0.959401.144500.259200.1590*
H10A0.966601.107700.135700.1600*
H11A0.913300.972200.079200.1270*
H13A0.825300.810600.079100.1760*
H14A0.761700.889200.195700.2670*
H15A0.647800.980400.213800.2550*
H16A0.605001.021900.102300.2610*
H17A0.666500.937100.017300.2030*
H19A0.903700.624500.277600.0910*
H20A0.906500.483400.320800.0910*
H22A0.751200.411000.094700.0780*
H23A0.748500.552800.053200.0720*
H25A0.944100.333000.338400.1420*
H25B0.869300.259200.329700.1420*
H25C0.852500.354200.355900.1420*
H26A0.714000.294400.159900.1690*
H26B0.783600.222900.212200.1690*
H26C0.804000.269700.141100.1690*
H1B0.480000.721600.227700.089 (10)*
H7B0.539500.820500.327000.0960*
H8B0.498500.831300.465300.1290*
H9B0.528800.718600.536600.1610*
H10B0.602200.593200.471400.1520*
H11B0.645700.581700.331200.1080*
H13B0.801000.529300.080800.1010*
H14B0.950800.489900.073200.1330*
H15B1.024800.566700.144400.1540*
H16B0.949000.681400.225700.1420*
H17B0.799600.720700.235300.1040*
H19B0.484100.818900.092500.0990*
H20B0.392200.831500.014600.1320*
H22B0.454900.586800.061500.1180*
H23B0.549100.575600.014000.0950*
H25D0.341700.842700.079800.4370*
H25E0.271100.792000.110400.4370*
H25F0.253600.796000.017300.4370*
H26D0.282800.653600.135100.3190*
H26E0.378100.608000.143300.3190*
H26F0.291400.600300.062100.3190*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0532 (14)0.0640 (16)0.0460 (13)0.0046 (12)0.0032 (11)0.0008 (12)
N3A0.0611 (15)0.0609 (16)0.0428 (13)0.0062 (12)0.0006 (11)0.0035 (12)
N24A0.0814 (19)0.0698 (19)0.0711 (18)0.0036 (15)0.0032 (14)0.0151 (15)
C2A0.0485 (16)0.066 (2)0.0386 (15)0.0036 (14)0.0001 (12)0.0038 (14)
C4A0.0624 (19)0.066 (2)0.0522 (18)0.0049 (16)0.0054 (14)0.0077 (15)
C5A0.0607 (19)0.062 (2)0.0543 (18)0.0029 (15)0.0011 (14)0.0027 (16)
C6A0.065 (2)0.063 (2)0.065 (2)0.0023 (16)0.0021 (16)0.0031 (18)
C7A0.083 (3)0.092 (3)0.095 (3)0.010 (2)0.028 (2)0.022 (2)
C8A0.130 (4)0.102 (4)0.134 (4)0.013 (3)0.045 (3)0.051 (3)
C9A0.158 (5)0.079 (3)0.138 (5)0.013 (3)0.026 (4)0.022 (3)
C10A0.199 (5)0.074 (3)0.102 (3)0.030 (3)0.024 (3)0.002 (3)
C11A0.146 (4)0.077 (3)0.070 (2)0.020 (3)0.008 (2)0.005 (2)
C12A0.085 (2)0.066 (2)0.065 (2)0.0176 (19)0.0205 (18)0.0201 (18)
C13A0.268 (7)0.094 (3)0.052 (2)0.018 (4)0.025 (3)0.018 (2)
C14A0.431 (13)0.107 (5)0.057 (3)0.003 (6)0.000 (5)0.026 (3)
C15A0.265 (10)0.138 (6)0.102 (5)0.072 (6)0.095 (6)0.047 (5)
C16A0.135 (5)0.174 (7)0.248 (9)0.009 (4)0.047 (6)0.118 (7)
C17A0.091 (3)0.194 (5)0.196 (5)0.038 (4)0.018 (3)0.126 (5)
C18A0.0471 (16)0.0626 (19)0.0405 (15)0.0011 (13)0.0027 (12)0.0046 (14)
C19A0.082 (2)0.079 (2)0.0440 (17)0.0184 (18)0.0049 (15)0.0038 (16)
C20A0.077 (2)0.085 (2)0.0441 (17)0.0094 (18)0.0039 (15)0.0151 (17)
C21A0.0459 (16)0.067 (2)0.0572 (18)0.0017 (14)0.0079 (14)0.0087 (16)
C22A0.0607 (19)0.066 (2)0.0529 (18)0.0048 (15)0.0029 (14)0.0022 (15)
C23A0.0582 (18)0.069 (2)0.0383 (15)0.0009 (15)0.0009 (13)0.0006 (14)
C25A0.096 (3)0.092 (3)0.083 (3)0.007 (2)0.016 (2)0.028 (2)
C26A0.132 (4)0.065 (2)0.112 (3)0.005 (2)0.009 (3)0.004 (2)
N1B0.0489 (14)0.0685 (16)0.0374 (12)0.0035 (11)0.0040 (11)0.0005 (11)
N3B0.0467 (14)0.0700 (16)0.0364 (12)0.0005 (12)0.0044 (10)0.0031 (11)
N24B0.117 (3)0.249 (6)0.111 (3)0.017 (4)0.069 (3)0.042 (3)
C2B0.0479 (16)0.0624 (18)0.0357 (14)0.0022 (14)0.0037 (12)0.0005 (13)
C4B0.0498 (17)0.0654 (18)0.0381 (15)0.0025 (14)0.0086 (12)0.0022 (13)
C5B0.0524 (17)0.0644 (19)0.0394 (15)0.0021 (14)0.0090 (13)0.0008 (13)
C6B0.0657 (19)0.077 (2)0.0389 (15)0.0007 (16)0.0106 (14)0.0046 (15)
C7B0.083 (2)0.096 (3)0.0510 (19)0.004 (2)0.0130 (17)0.0125 (18)
C8B0.126 (3)0.130 (4)0.054 (2)0.011 (3)0.015 (2)0.025 (2)
C9B0.178 (5)0.164 (5)0.045 (2)0.010 (4)0.022 (3)0.009 (3)
C10B0.177 (5)0.144 (4)0.055 (2)0.015 (4)0.037 (3)0.020 (3)
C11B0.116 (3)0.101 (3)0.0478 (19)0.004 (2)0.0233 (19)0.0087 (19)
C12B0.0499 (17)0.082 (2)0.0433 (16)0.0009 (16)0.0029 (14)0.0090 (15)
C13B0.066 (2)0.113 (3)0.062 (2)0.021 (2)0.0082 (17)0.004 (2)
C14B0.079 (3)0.158 (4)0.075 (3)0.045 (3)0.001 (2)0.019 (3)
C15B0.065 (3)0.213 (6)0.099 (4)0.009 (4)0.019 (3)0.070 (4)
C16B0.082 (3)0.177 (5)0.108 (4)0.029 (3)0.049 (3)0.046 (3)
C17B0.072 (2)0.114 (3)0.084 (2)0.009 (2)0.039 (2)0.009 (2)
C18B0.0470 (16)0.073 (2)0.0371 (15)0.0029 (15)0.0031 (12)0.0041 (14)
C19B0.088 (2)0.103 (3)0.056 (2)0.020 (2)0.0235 (19)0.0014 (18)
C20B0.094 (3)0.160 (4)0.074 (3)0.041 (3)0.026 (2)0.017 (3)
C21B0.073 (3)0.172 (5)0.060 (2)0.020 (3)0.025 (2)0.032 (3)
C22B0.105 (3)0.126 (4)0.075 (3)0.031 (3)0.044 (2)0.005 (2)
C23B0.088 (2)0.089 (3)0.066 (2)0.004 (2)0.0353 (19)0.0015 (19)
C25B0.220 (8)0.500 (17)0.201 (8)0.127 (10)0.133 (7)0.049 (9)
C26B0.181 (6)0.353 (11)0.154 (5)0.121 (7)0.121 (5)0.066 (6)
Geometric parameters (Å, º) top
N1A—C2A1.333 (4)C22A—H22A0.9300
N1A—C5A1.385 (4)C23A—H23A0.9300
N3A—C2A1.357 (3)C25A—H25A0.9600
N3A—C4A1.375 (4)C25A—H25C0.9600
N24A—C21A1.372 (4)C25A—H25B0.9600
N24A—C25A1.443 (4)C26A—H26A0.9600
N24A—C26A1.438 (4)C26A—H26C0.9600
N3A—H3A1.0200C26A—H26B0.9600
N1B—C2B1.358 (3)C2B—C18B1.460 (4)
N1B—C5B1.371 (4)C4B—C12B1.472 (4)
N3B—C4B1.385 (3)C4B—C5B1.369 (4)
N3B—C2B1.323 (4)C5B—C6B1.471 (4)
N24B—C21B1.408 (6)C6B—C11B1.373 (5)
N24B—C26B1.423 (10)C6B—C7B1.383 (4)
N24B—C25B1.399 (12)C7B—C8B1.376 (4)
N1B—H1B1.0100C8B—C9B1.344 (7)
C2A—C18A1.457 (4)C9B—C10B1.374 (7)
C4A—C12A1.475 (4)C10B—C11B1.394 (5)
C4A—C5A1.366 (4)C12B—C13B1.373 (4)
C5A—C6A1.466 (4)C12B—C17B1.379 (5)
C6A—C11A1.380 (5)C13B—C14B1.390 (6)
C6A—C7A1.382 (5)C14B—C15B1.357 (7)
C7A—C8A1.379 (6)C15B—C16B1.361 (9)
C8A—C9A1.369 (8)C16B—C17B1.377 (7)
C9A—C10A1.361 (8)C18B—C23B1.362 (4)
C10A—C11A1.384 (6)C18B—C19B1.377 (5)
C12A—C17A1.366 (7)C19B—C20B1.384 (5)
C12A—C13A1.323 (6)C20B—C21B1.378 (7)
C13A—C14A1.376 (7)C21B—C22B1.361 (7)
C14A—C15A1.243 (13)C22B—C23B1.383 (5)
C15A—C16A1.416 (11)C7B—H7B0.9300
C16A—C17A1.410 (10)C8B—H8B0.9300
C18A—C19A1.385 (4)C9B—H9B0.9300
C18A—C23A1.383 (4)C10B—H10B0.9300
C19A—C20A1.371 (4)C11B—H11B0.9300
C20A—C21A1.381 (4)C13B—H13B0.9300
C21A—C22A1.401 (4)C14B—H14B0.9300
C22A—C23A1.369 (4)C15B—H15B0.9300
C7A—H7A0.9300C16B—H16B0.9300
C8A—H8A0.9300C17B—H17B0.9300
C9A—H9A0.9300C19B—H19B0.9300
C10A—H10A0.9300C20B—H20B0.9300
C11A—H11A0.9300C22B—H22B0.9300
C13A—H13A0.9300C23B—H23B0.9300
C14A—H14A0.9300C25B—H25D0.9600
C15A—H15A0.9300C25B—H25E0.9600
C16A—H16A0.9300C25B—H25F0.9600
C17A—H17A0.9300C26B—H26D0.9600
C19A—H19A0.9300C26B—H26E0.9600
C20A—H20A0.9300C26B—H26F0.9600
C2A—N1A—C5A106.0 (2)H25B—C25A—H25C109.00
C2A—N3A—C4A108.0 (2)H26A—C26A—H26C109.00
C21A—N24A—C25A120.8 (3)H26B—C26A—H26C109.00
C21A—N24A—C26A120.9 (3)N24A—C26A—H26C109.00
C25A—N24A—C26A118.1 (3)H26A—C26A—H26B110.00
C2A—N3A—H3A123.00N24A—C26A—H26A109.00
C4A—N3A—H3A129.00N24A—C26A—H26B109.00
C2B—N1B—C5B108.0 (2)N1B—C2B—N3B110.9 (2)
C2B—N3B—C4B105.7 (2)N1B—C2B—C18B122.8 (3)
C25B—N24B—C26B118.8 (6)N3B—C2B—C18B126.3 (2)
C21B—N24B—C26B120.0 (6)N3B—C4B—C5B109.9 (3)
C21B—N24B—C25B117.7 (6)C5B—C4B—C12B129.7 (3)
C5B—N1B—H1B126.00N3B—C4B—C12B120.3 (2)
C2B—N1B—H1B123.00C4B—C5B—C6B134.0 (3)
N1A—C2A—N3A110.4 (3)N1B—C5B—C6B120.3 (2)
N3A—C2A—C18A124.0 (2)N1B—C5B—C4B105.5 (2)
N1A—C2A—C18A125.5 (2)C5B—C6B—C7B121.5 (3)
N3A—C4A—C5A106.0 (2)C5B—C6B—C11B119.6 (3)
C5A—C4A—C12A133.2 (3)C7B—C6B—C11B118.7 (3)
N3A—C4A—C12A120.8 (3)C6B—C7B—C8B121.0 (3)
N1A—C5A—C6A120.9 (3)C7B—C8B—C9B120.0 (4)
N1A—C5A—C4A109.6 (3)C8B—C9B—C10B120.7 (3)
C4A—C5A—C6A129.4 (3)C9B—C10B—C11B119.6 (4)
C7A—C6A—C11A117.9 (3)C6B—C11B—C10B120.0 (4)
C5A—C6A—C11A121.5 (3)C13B—C12B—C17B118.4 (3)
C5A—C6A—C7A120.6 (3)C4B—C12B—C13B120.3 (3)
C6A—C7A—C8A121.1 (4)C4B—C12B—C17B121.2 (3)
C7A—C8A—C9A119.7 (5)C12B—C13B—C14B120.4 (3)
C8A—C9A—C10A120.4 (5)C13B—C14B—C15B120.5 (4)
C9A—C10A—C11A119.8 (5)C14B—C15B—C16B119.4 (5)
C6A—C11A—C10A121.1 (4)C15B—C16B—C17B120.8 (5)
C13A—C12A—C17A117.9 (4)C12B—C17B—C16B120.5 (4)
C4A—C12A—C13A122.5 (4)C19B—C18B—C23B116.4 (3)
C4A—C12A—C17A119.6 (4)C2B—C18B—C19B122.0 (3)
C12A—C13A—C14A121.8 (6)C2B—C18B—C23B121.6 (3)
C13A—C14A—C15A122.5 (7)C18B—C19B—C20B121.5 (4)
C14A—C15A—C16A120.2 (7)C19B—C20B—C21B121.4 (4)
C15A—C16A—C17A116.9 (6)N24B—C21B—C22B121.2 (5)
C12A—C17A—C16A120.4 (5)N24B—C21B—C20B121.9 (5)
C19A—C18A—C23A115.8 (3)C20B—C21B—C22B116.9 (4)
C2A—C18A—C23A123.4 (2)C21B—C22B—C23B121.4 (4)
C2A—C18A—C19A120.8 (2)C18B—C23B—C22B122.3 (3)
C18A—C19A—C20A122.7 (3)C6B—C7B—H7B120.00
C19A—C20A—C21A121.3 (3)C8B—C7B—H7B119.00
C20A—C21A—C22A116.6 (3)C7B—C8B—H8B120.00
N24A—C21A—C20A122.1 (3)C9B—C8B—H8B120.00
N24A—C21A—C22A121.4 (3)C8B—C9B—H9B120.00
C21A—C22A—C23A121.2 (3)C10B—C9B—H9B120.00
C18A—C23A—C22A122.4 (3)C9B—C10B—H10B120.00
C8A—C7A—H7A119.00C11B—C10B—H10B120.00
C6A—C7A—H7A119.00C6B—C11B—H11B120.00
C9A—C8A—H8A120.00C10B—C11B—H11B120.00
C7A—C8A—H8A120.00C12B—C13B—H13B120.00
C10A—C9A—H9A120.00C14B—C13B—H13B120.00
C8A—C9A—H9A120.00C13B—C14B—H14B120.00
C11A—C10A—H10A120.00C15B—C14B—H14B120.00
C9A—C10A—H10A120.00C14B—C15B—H15B120.00
C6A—C11A—H11A119.00C16B—C15B—H15B120.00
C10A—C11A—H11A120.00C15B—C16B—H16B120.00
C14A—C13A—H13A119.00C17B—C16B—H16B120.00
C12A—C13A—H13A119.00C12B—C17B—H17B120.00
C13A—C14A—H14A119.00C16B—C17B—H17B120.00
C15A—C14A—H14A119.00C18B—C19B—H19B119.00
C16A—C15A—H15A120.00C20B—C19B—H19B119.00
C14A—C15A—H15A120.00C19B—C20B—H20B119.00
C17A—C16A—H16A122.00C21B—C20B—H20B119.00
C15A—C16A—H16A122.00C21B—C22B—H22B119.00
C12A—C17A—H17A120.00C23B—C22B—H22B119.00
C16A—C17A—H17A120.00C18B—C23B—H23B119.00
C18A—C19A—H19A119.00C22B—C23B—H23B119.00
C20A—C19A—H19A119.00N24B—C25B—H25D109.00
C21A—C20A—H20A119.00N24B—C25B—H25E109.00
C19A—C20A—H20A119.00N24B—C25B—H25F109.00
C21A—C22A—H22A119.00H25D—C25B—H25E109.00
C23A—C22A—H22A119.00H25D—C25B—H25F110.00
C22A—C23A—H23A119.00H25E—C25B—H25F109.00
C18A—C23A—H23A119.00N24B—C26B—H26D110.00
H25A—C25A—H25B110.00N24B—C26B—H26E109.00
N24A—C25A—H25C109.00N24B—C26B—H26F109.00
N24A—C25A—H25B109.00H26D—C26B—H26E110.00
H25A—C25A—H25C109.00H26D—C26B—H26F109.00
N24A—C25A—H25A109.00H26E—C26B—H26F109.00
C5A—N1A—C2A—N3A0.1 (3)C14A—C15A—C16A—C17A6.7 (12)
C5A—N1A—C2A—C18A179.6 (3)C15A—C16A—C17A—C12A4.9 (10)
C2A—N1A—C5A—C4A0.8 (3)C2A—C18A—C19A—C20A178.9 (3)
C2A—N1A—C5A—C6A180.0 (3)C23A—C18A—C19A—C20A0.1 (5)
C4A—N3A—C2A—N1A0.6 (3)C2A—C18A—C23A—C22A179.1 (3)
C4A—N3A—C2A—C18A179.7 (3)C19A—C18A—C23A—C22A0.3 (5)
C2A—N3A—C4A—C5A1.0 (3)C18A—C19A—C20A—C21A0.3 (5)
C2A—N3A—C4A—C12A177.5 (3)C19A—C20A—C21A—C22A0.5 (5)
C25A—N24A—C21A—C20A0.7 (5)C19A—C20A—C21A—N24A179.6 (3)
C25A—N24A—C21A—C22A178.3 (3)C20A—C21A—C22A—C23A0.4 (5)
C26A—N24A—C21A—C20A175.8 (3)N24A—C21A—C22A—C23A179.4 (3)
C26A—N24A—C21A—C22A3.2 (5)C21A—C22A—C23A—C18A0.0 (5)
C2B—N1B—C5B—C6B173.2 (3)N1B—C2B—C18B—C19B45.5 (4)
C5B—N1B—C2B—N3B2.0 (3)N1B—C2B—C18B—C23B133.4 (3)
C5B—N1B—C2B—C18B178.2 (3)N3B—C2B—C18B—C19B134.2 (3)
C2B—N1B—C5B—C4B2.6 (3)N3B—C2B—C18B—C23B46.9 (4)
C4B—N3B—C2B—C18B179.8 (3)N3B—C4B—C5B—N1B2.4 (3)
C2B—N3B—C4B—C5B1.2 (3)N3B—C4B—C5B—C6B172.7 (3)
C2B—N3B—C4B—C12B174.9 (3)C12B—C4B—C5B—N1B173.3 (3)
C4B—N3B—C2B—N1B0.5 (3)C12B—C4B—C5B—C6B11.7 (5)
C25B—N24B—C21B—C20B5.3 (7)N3B—C4B—C12B—C13B35.6 (4)
C25B—N24B—C21B—C22B175.8 (5)N3B—C4B—C12B—C17B140.6 (3)
C26B—N24B—C21B—C20B163.9 (5)C5B—C4B—C12B—C13B149.1 (3)
C26B—N24B—C21B—C22B17.3 (7)C5B—C4B—C12B—C17B34.7 (5)
N1A—C2A—C18A—C23A176.0 (3)N1B—C5B—C6B—C7B43.8 (4)
N3A—C2A—C18A—C19A176.9 (3)N1B—C5B—C6B—C11B131.1 (3)
N1A—C2A—C18A—C19A2.8 (5)C4B—C5B—C6B—C7B141.7 (3)
N3A—C2A—C18A—C23A4.3 (5)C4B—C5B—C6B—C11B43.3 (5)
N3A—C4A—C12A—C17A116.5 (4)C5B—C6B—C7B—C8B174.6 (3)
C5A—C4A—C12A—C13A120.5 (5)C11B—C6B—C7B—C8B0.4 (5)
N3A—C4A—C12A—C13A61.5 (6)C5B—C6B—C11B—C10B174.2 (4)
N3A—C4A—C5A—N1A1.1 (4)C7B—C6B—C11B—C10B0.8 (6)
N3A—C4A—C5A—C6A179.7 (3)C6B—C7B—C8B—C9B0.2 (7)
C12A—C4A—C5A—N1A177.2 (4)C7B—C8B—C9B—C10B0.4 (8)
C12A—C4A—C5A—C6A2.0 (6)C8B—C9B—C10B—C11B0.0 (9)
C5A—C4A—C12A—C17A61.5 (6)C9B—C10B—C11B—C6B0.6 (8)
C4A—C5A—C6A—C7A142.1 (4)C4B—C12B—C13B—C14B178.3 (3)
N1A—C5A—C6A—C7A37.0 (5)C17B—C12B—C13B—C14B2.0 (5)
N1A—C5A—C6A—C11A141.4 (4)C4B—C12B—C17B—C16B177.9 (4)
C4A—C5A—C6A—C11A39.6 (5)C13B—C12B—C17B—C16B1.6 (5)
C5A—C6A—C7A—C8A179.8 (4)C12B—C13B—C14B—C15B1.4 (6)
C11A—C6A—C7A—C8A1.8 (6)C13B—C14B—C15B—C16B0.4 (8)
C5A—C6A—C11A—C10A178.8 (4)C14B—C15B—C16B—C17B0.1 (8)
C7A—C6A—C11A—C10A0.4 (6)C15B—C16B—C17B—C12B0.7 (7)
C6A—C7A—C8A—C9A2.0 (7)C2B—C18B—C19B—C20B176.9 (3)
C7A—C8A—C9A—C10A0.8 (8)C23B—C18B—C19B—C20B2.1 (5)
C8A—C9A—C10A—C11A0.6 (9)C2B—C18B—C23B—C22B176.1 (3)
C9A—C10A—C11A—C6A0.8 (8)C19B—C18B—C23B—C22B2.9 (5)
C17A—C12A—C13A—C14A0.6 (8)C18B—C19B—C20B—C21B0.5 (6)
C4A—C12A—C17A—C16A179.9 (5)C19B—C20B—C21B—N24B178.8 (4)
C4A—C12A—C13A—C14A178.7 (5)C19B—C20B—C21B—C22B2.3 (6)
C13A—C12A—C17A—C16A2.0 (8)N24B—C21B—C22B—C23B179.6 (4)
C12A—C13A—C14A—C15A2.6 (11)C20B—C21B—C22B—C23B1.5 (6)
C13A—C14A—C15A—C16A5.6 (13)C21B—C22B—C23B—C18B1.1 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1B—H1B···N1Ai1.011.922.899 (3)163
N3A—H3A···N3B1.021.922.890 (3)157
C19A—H19A···N1A0.932.632.943 (4)100
Symmetry code: (i) x1/2, y+3/2, z1/2.

Experimental details

Crystal data
Chemical formulaC23H21N3
Mr339.43
Crystal system, space groupMonoclinic, P21/n
Temperature (K)296
a, b, c (Å)15.228 (4), 15.215 (4), 17.641 (4)
β (°) 110.974 (4)
V3)3816.5 (17)
Z8
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.24 × 0.19 × 0.17
Data collection
DiffractometerOxford Xcalibur Eos (Nova) CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
36558, 6983, 3921
Rint0.063
(sin θ/λ)max1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.070, 0.175, 1.02
No. of reflections6983
No. of parameters475
No. of restraints0
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.17

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1B—H1B···N1Ai1.011.922.899 (3)163
N3A—H3A···N3B1.021.922.890 (3)157
Symmetry code: (i) x1/2, y+3/2, z1/2.
references
References top

Akkurt, M., Fronczek, F. R., Mohammed, S. K., Talybov, A. H., Marzouk, A. A. E. & Abdelhamid, A. A. (2013). Acta Cryst. E69, o527–o528.

Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., Streek, J. & Wood, P. A. (2008). J. Appl.Cryst. 41, 466.

Oxford Diffraction (2009). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.

Prabhuswamy, M., Madan Kumar, S., Muneer, C. P., Shafi, P. M. & Lokanath, N. K. (2013). Acta Cryst. E69, o174.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.

Ucucu, U., Karaburun, N. G. & Iskdag, I. (2001). Il Farmaco, 56, 285–290.

Yanover, D. & Kaftory, M. (2009). Acta Cryst. E65, o711.