A second monoclinic polymorph of 4-[(E)-(4-benzyl­oxybenzyl­idene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Kant, R.; Gupta, V.K.; Kapoor, K.; Nayak, P.S.; Sarojini, B.K.; Narayana, B.

doi:10.1107/S1600536812050891

organic compounds

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ISSN: 2056-9890

Volume 69| Part 1| January 2013| Page o115

https://doi.org/10.1107/S1600536812050891

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A second monoclinic polymorph of 4-[(E)-(4-benzyloxybenzylidene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Rajni Kant,^a ^* Vivek K. Gupta,^a Kamini Kapoor,^a Prakash S. Nayak,^b B. K. Sarojini ^c and B. Narayana ^b

^aX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Chemistry, P.A. College of Engineering, Nadupadavu, Mangalore 574 153, India
^*Correspondence e-mail: rkvk.paper11@gmail.com

(Received 5 December 2012; accepted 14 December 2012; online 19 December 2012)

In the title compound, C₂₅H₂₃N₃O₂, the central benzene ring makes dihedral angles of 77.14 (8) and 87.7 (2)° with the terminal benzene rings and an angle of 1.9 (1)° with the pyrazolone ring. The benzene ring and the N atom of the pyrazole ring bearing the phenyl substituent are disordered over two sets of sites with an occupancy ratio of 0.71 (2):0.29 (2). The N atoms of the pyrazole ring have a pyramidal environment, the sums of the valence angles around them being 354.6 (3) and 352.0 (6)/349.5 (15)°. In the crystal, molecules are packed into layers parallel to the ac plane. The other monoclinic polymorphic form was reported recently [Dutkiewicz et al. (2012 ). Acta Cryst. E68, o1324].

Related literature

For potential applications of Schiff bases, see: Patole et al. (2006 ); Shi et al.(2007 ); Satyanarayana et al. (2008 ). For related structures, see: Liu et al.(2008 ); Hu, (2006 ). For the other monoclinic polymorph, see Dutkiewicz et al., (2012).

Experimental

Crystal data

C₂₅H₂₃N₃O₂
M_r = 397.46
Monoclinic, P 2₁ /n
a = 13.0079 (5) Å
b = 9.9079 (4) Å
c = 17.0469 (9) Å
β = 103.674 (4)°
V = 2134.75 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.920, T_max = 1.000
19519 measured reflections
4162 independent reflections
2399 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.154
S = 1.03
4162 reflections
292 parameters
12 restraints
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812050891/gk2544sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812050891/gk2544Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812050891/gk2544Isup3.cml

checkCIF report

Comment top

Schiff bases are widely used organic compounds and structurally it is a nitrogen analogue of an aldehyde or ketone in which the carbonyl group has been replaced by an imine or azomethine group. They are used as pigments and dyes, catalysts, intermediates in organic synthesis, and polymer stabilisers. Schiff bases have also been shown to exhibit a broad range of biological activities including antimicrobial (Shi et al., 2007; Satyanarayana et al., 2008; antimycobacterial (Patole et al., 2006). In view of the pharmacological importance of schiff base derivatives, the title compound (I) is prepared and its crystal structure is reported.

All bond lengths and angles are normal and correspond to those observed in related structures(Liu et al., 2008; Hu, 2006; Dutkiewicz et al., 2012). The central benzene ring makes dihedral angles of 77.14 (8), 87.7 (2) and 87.1 (6)° with the terminal benzene rings (C24—C29),(C8—C13A)and (C8—C13B) respectively while 1.9 (1)(N2A)/ 1.7 (1)°(N2B) with the pyrazolone ring. The benzene ring (C8—C13) and atom N2 are disordered over two positions with an occupancy ratio of 0.71 (2):0.29 (2). The N atoms of the pyrazole ring have a pyramidal environment, the sums of the valence angles around them being 354.6 (3)(N1) and 352.0 (6)(N2A) / 349.5 (15)(N2B) °. The sums of the valence angles around N-atoms of the pyrazole ring in the polymorph of this compound are 353.5 for N1 and 347.3 ° for N2 (Dutkiewicz et al., 2012). Molecules are packed into layers parallel to the ac-plane (Fig.2).

Related literature top

For potential applications of Schiff bases, see: Patole et al. (2006); Shi et al.(2007); Satyanarayana et al. (2008). For related structures, see: Liu et al.(2008); Hu, (2006). For the other monoclinic polymorph, see Dutkiewicz et al., (2012).

Experimental top

The title compound was synthesized by adding 4-benzyloxybenzaldehyde (0.212 g, 1 mmol) to the solution of 4-aminoantipyrine (0.203 g, 1 mmol) in methanol (30 ml) containing few drops of conc. sulfuric acid. The mixture was refluxed for 3hrs and left stirring overnight at room temperature. The resultant solid obtained was then filtered. Yellow needle-shaped single crystals suitable for X-ray structure determination were formed after slow evaporation of dichloromethane at room temperature (431–433 K).

Structure description top

For potential applications of Schiff bases, see: Patole et al. (2006); Shi et al.(2007); Satyanarayana et al. (2008). For related structures, see: Liu et al.(2008); Hu, (2006). For the other monoclinic polymorph, see Dutkiewicz et al., (2012).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction ,2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. ORTEP view of the molecule with the atom-labeling scheme. The displacement ellipsoids are drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The packing arrangement of molecules viewed down the b axis. Hydrogen atoms have been omitted for clarity.

4-[(E)-(4-Benzyloxybenzylidene)amino]-1,5-dimethyl-2-phenyl- 1H-pyrazol-3(2H)-one top

Crystal data top

C₂₅H₂₃N₃O₂	F(000) = 840
M_r = 397.46	D_x = 1.237 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7057 reflections
a = 13.0079 (5) Å	θ = 3.6–29.0°
b = 9.9079 (4) Å	µ = 0.08 mm⁻¹
c = 17.0469 (9) Å	T = 293 K
β = 103.674 (4)°	Plate, white
V = 2134.75 (16) Å³	0.3 × 0.2 × 0.2 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	4162 independent reflections
Radiation source: fine-focus sealed tube	2399 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
Detector resolution: 16.1049 pixels mm^-1	θ_max = 26.0°, θ_min = 3.6°
ω scans	h = −15→16
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −12→12
T_min = 0.920, T_max = 1.000	l = −21→21
19519 measured reflections

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.057P)² + 0.3022P] where P = (F_o² + 2F_c²)/3
4162 reflections	(Δ/σ)_max = 0.001
292 parameters	Δρ_max = 0.21 e Å⁻³
12 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₂₅H₂₃N₃O₂	V = 2134.75 (16) Å³
M_r = 397.46	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.0079 (5) Å	µ = 0.08 mm⁻¹
b = 9.9079 (4) Å	T = 293 K
c = 17.0469 (9) Å	0.3 × 0.2 × 0.2 mm
β = 103.674 (4)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	4162 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	2399 reflections with I > 2σ(I)
T_min = 0.920, T_max = 1.000	R_int = 0.047
19519 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	12 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 1.03	Δρ_max = 0.21 e Å⁻³
4162 reflections	Δρ_min = −0.15 e Å⁻³
292 parameters

Special details top

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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)
N1	0.74159 (14)	−0.03151 (19)	−0.14892 (13)	0.0628 (5)
N2A	0.8373 (6)	0.0248 (9)	−0.1606 (6)	0.0613 (17)	0.707 (17)
C9A	0.9286 (11)	−0.0547 (11)	−0.2496 (4)	0.0742 (16)	0.707 (17)
H9A	0.8866	0.0057	−0.2850	0.089*	0.707 (17)
C10A	1.0017 (8)	−0.1332 (10)	−0.2750 (6)	0.091 (2)	0.707 (17)
H10A	1.0089	−0.1260	−0.3278	0.109*	0.707 (17)
C11A	1.0640 (6)	−0.2218 (8)	−0.2229 (7)	0.083 (3)	0.707 (17)
H11A	1.1114	−0.2774	−0.2408	0.100*	0.707 (17)
C12A	1.0560 (6)	−0.2277 (9)	−0.1448 (6)	0.092 (3)	0.707 (17)
H12A	1.1003	−0.2849	−0.1087	0.110*	0.707 (17)
C13A	0.9831 (12)	−0.1502 (15)	−0.1191 (5)	0.080 (2)	0.707 (17)
H13A	0.9779	−0.1548	−0.0657	0.096*	0.707 (17)
N2B	0.8462 (17)	0.001 (2)	−0.1335 (11)	0.0613 (17)	0.293 (17)
C9B	0.940 (3)	−0.089 (3)	−0.2461 (10)	0.0742 (16)	0.293 (17)
H9B	0.8994	−0.0473	−0.2919	0.089*	0.293 (17)
C10B	1.021 (2)	−0.173 (3)	−0.2531 (15)	0.091 (2)	0.293 (17)
H10B	1.0390	−0.1891	−0.3021	0.109*	0.293 (17)
C11B	1.074 (2)	−0.233 (3)	−0.1820 (14)	0.083 (3)	0.293 (17)
H11B	1.1310	−0.2881	−0.1851	0.100*	0.293 (17)
C12B	1.054 (2)	−0.220 (3)	−0.1069 (13)	0.092 (3)	0.293 (17)
H12B	1.0900	−0.2679	−0.0622	0.110*	0.293 (17)
C13B	0.974 (3)	−0.129 (4)	−0.1031 (11)	0.080 (2)	0.293 (17)
H13B	0.9589	−0.1105	−0.0537	0.096*	0.293 (17)
O3	0.93832 (13)	0.21006 (18)	−0.11143 (13)	0.0865 (6)
C3	0.85441 (18)	0.1476 (2)	−0.12022 (15)	0.0626 (7)
C4	0.75575 (16)	0.1790 (2)	−0.10095 (13)	0.0503 (5)
C5	0.69005 (16)	0.0687 (2)	−0.11997 (14)	0.0530 (6)
C6	0.6960 (2)	−0.1478 (3)	−0.1940 (2)	0.1129 (13)
H6A	0.6383	−0.1805	−0.1731	0.169*
H6B	0.7487	−0.2171	−0.1893	0.169*
H6C	0.6705	−0.1238	−0.2498	0.169*
C7	0.57995 (17)	0.0514 (3)	−0.11114 (17)	0.0737 (8)
H7A	0.5331	0.0412	−0.1635	0.111*
H7B	0.5596	0.1294	−0.0849	0.111*
H7C	0.5760	−0.0274	−0.0793	0.111*
C8	0.91815 (17)	−0.0660 (2)	−0.17219 (15)	0.0558 (6)
N14	0.72512 (13)	0.29631 (18)	−0.06847 (11)	0.0517 (5)
C15	0.78748 (17)	0.3983 (2)	−0.05482 (13)	0.0542 (6)
H15	0.8538	0.3918	−0.0661	0.065*
C16	0.75724 (16)	0.5243 (2)	−0.02202 (13)	0.0496 (5)
C17	0.65779 (17)	0.5437 (2)	−0.00752 (14)	0.0601 (6)
H17	0.6080	0.4748	−0.0196	0.072*
C18	0.63120 (17)	0.6619 (2)	0.02411 (15)	0.0619 (6)
H18	0.5636	0.6731	0.0325	0.074*
C19	0.70499 (17)	0.7655 (2)	0.04375 (13)	0.0506 (5)
C20	0.80368 (18)	0.7488 (2)	0.02936 (14)	0.0573 (6)
H20	0.8534	0.8178	0.0415	0.069*
C21	0.82894 (18)	0.6293 (2)	−0.00321 (15)	0.0588 (6)
H21	0.8960	0.6191	−0.0128	0.071*
O22	0.67048 (11)	0.87620 (16)	0.07728 (10)	0.0647 (5)
C23	0.74356 (17)	0.9854 (2)	0.10298 (15)	0.0583 (6)
H23A	0.7578	1.0319	0.0566	0.070*
H23B	0.8098	0.9516	0.1359	0.070*
C24	0.69226 (16)	1.0782 (2)	0.15077 (14)	0.0522 (6)
C25	0.64419 (18)	1.1960 (2)	0.11844 (15)	0.0642 (7)
H25	0.6458	1.2212	0.0662	0.077*
C26	0.5933 (2)	1.2772 (3)	0.16364 (19)	0.0761 (8)
H26	0.5612	1.3570	0.1417	0.091*
C27	0.5903 (2)	1.2403 (3)	0.2406 (2)	0.0822 (9)
H27	0.5551	1.2941	0.2705	0.099*
C28	0.6390 (2)	1.1244 (3)	0.27318 (17)	0.0788 (8)
H28	0.6375	1.0996	0.3255	0.095*
C29	0.68990 (19)	1.0448 (3)	0.22883 (15)	0.0652 (7)
H29	0.7236	0.9666	0.2518	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0479 (11)	0.0503 (12)	0.0897 (15)	−0.0096 (9)	0.0154 (9)	−0.0168 (11)
N2A	0.0523 (19)	0.052 (3)	0.085 (5)	−0.0073 (19)	0.026 (3)	−0.016 (3)
C9A	0.095 (4)	0.053 (6)	0.074 (2)	0.014 (4)	0.018 (2)	−0.011 (2)
C10A	0.120 (5)	0.069 (6)	0.094 (5)	0.005 (4)	0.047 (4)	−0.019 (3)
C11A	0.071 (3)	0.061 (3)	0.120 (8)	0.001 (2)	0.027 (5)	−0.029 (5)
C12A	0.082 (3)	0.072 (3)	0.111 (8)	0.010 (2)	0.004 (6)	0.021 (7)
C13A	0.081 (3)	0.076 (6)	0.085 (3)	−0.003 (2)	0.023 (3)	0.012 (4)
N2B	0.0523 (19)	0.052 (3)	0.085 (5)	−0.0073 (19)	0.026 (3)	−0.016 (3)
C9B	0.095 (4)	0.053 (6)	0.074 (2)	0.014 (4)	0.018 (2)	−0.011 (2)
C10B	0.120 (5)	0.069 (6)	0.094 (5)	0.005 (4)	0.047 (4)	−0.019 (3)
C11B	0.071 (3)	0.061 (3)	0.120 (8)	0.001 (2)	0.027 (5)	−0.029 (5)
C12B	0.082 (3)	0.072 (3)	0.111 (8)	0.010 (2)	0.004 (6)	0.021 (7)
C13B	0.081 (3)	0.076 (6)	0.085 (3)	−0.003 (2)	0.023 (3)	0.012 (4)
O3	0.0631 (10)	0.0667 (12)	0.1405 (17)	−0.0236 (9)	0.0459 (11)	−0.0353 (12)
C3	0.0549 (14)	0.0537 (15)	0.0823 (17)	−0.0109 (12)	0.0225 (12)	−0.0157 (13)
C4	0.0473 (12)	0.0464 (13)	0.0565 (13)	−0.0036 (10)	0.0109 (10)	−0.0041 (11)
C5	0.0475 (12)	0.0478 (13)	0.0614 (14)	−0.0043 (10)	0.0087 (10)	−0.0041 (11)
C6	0.0795 (19)	0.093 (2)	0.169 (3)	−0.0320 (17)	0.036 (2)	−0.077 (2)
C7	0.0510 (14)	0.0625 (17)	0.107 (2)	−0.0074 (12)	0.0179 (13)	−0.0091 (15)
C8	0.0524 (13)	0.0467 (13)	0.0708 (16)	−0.0081 (11)	0.0198 (11)	−0.0080 (12)
N14	0.0528 (10)	0.0448 (11)	0.0569 (11)	−0.0055 (9)	0.0118 (8)	−0.0037 (9)
C15	0.0517 (12)	0.0514 (14)	0.0620 (15)	−0.0035 (11)	0.0182 (10)	−0.0038 (11)
C16	0.0503 (12)	0.0436 (12)	0.0553 (13)	−0.0017 (10)	0.0133 (10)	−0.0004 (10)
C17	0.0502 (13)	0.0492 (14)	0.0800 (17)	−0.0103 (11)	0.0136 (11)	−0.0114 (12)
C18	0.0448 (12)	0.0567 (15)	0.0838 (17)	−0.0063 (11)	0.0144 (11)	−0.0148 (13)
C19	0.0514 (12)	0.0436 (13)	0.0556 (13)	−0.0005 (10)	0.0104 (10)	−0.0030 (10)
C20	0.0576 (14)	0.0453 (13)	0.0713 (15)	−0.0138 (11)	0.0196 (11)	−0.0047 (11)
C21	0.0562 (13)	0.0502 (14)	0.0758 (16)	−0.0067 (11)	0.0269 (11)	−0.0055 (12)
O22	0.0539 (9)	0.0510 (10)	0.0889 (12)	−0.0065 (7)	0.0160 (8)	−0.0187 (9)
C23	0.0579 (13)	0.0472 (13)	0.0692 (15)	−0.0103 (11)	0.0139 (11)	−0.0051 (12)
C24	0.0509 (12)	0.0420 (13)	0.0609 (15)	−0.0090 (10)	0.0078 (10)	−0.0097 (11)
C25	0.0730 (16)	0.0533 (15)	0.0640 (15)	0.0010 (13)	0.0114 (12)	−0.0037 (13)
C26	0.0736 (17)	0.0580 (17)	0.092 (2)	0.0069 (13)	0.0099 (15)	−0.0164 (16)
C27	0.0699 (17)	0.086 (2)	0.093 (2)	−0.0173 (16)	0.0251 (16)	−0.0460 (19)
C28	0.094 (2)	0.082 (2)	0.0629 (17)	−0.0235 (18)	0.0235 (15)	−0.0181 (16)
C29	0.0727 (15)	0.0585 (16)	0.0612 (16)	−0.0133 (13)	0.0093 (12)	−0.0018 (13)

Geometric parameters (Å, º) top

N1—C5	1.355 (3)	C6—H6A	0.9600
N1—N2B	1.36 (2)	C6—H6B	0.9600
N1—N2A	1.421 (8)	C6—H6C	0.9600
N1—C6	1.434 (3)	C7—H7A	0.9600
N2A—C3	1.390 (8)	C7—H7B	0.9600
N2A—C8	1.433 (9)	C7—H7C	0.9600
C9A—C8	1.363 (5)	N14—C15	1.282 (3)
C9A—C10A	1.375 (6)	C15—C16	1.459 (3)
C9A—H9A	0.9300	C15—H15	0.9300
C10A—C11A	1.369 (6)	C16—C21	1.384 (3)
C10A—H10A	0.9300	C16—C17	1.387 (3)
C11A—C12A	1.361 (6)	C17—C18	1.367 (3)
C11A—H11A	0.9300	C17—H17	0.9300
C12A—C13A	1.370 (6)	C18—C19	1.391 (3)
C12A—H12A	0.9300	C18—H18	0.9300
C13A—C8	1.366 (5)	C19—O22	1.361 (2)
C13A—H13A	0.9300	C19—C20	1.373 (3)
N2B—C8	1.43 (2)	C20—C21	1.380 (3)
N2B—C3	1.47 (2)	C20—H20	0.9300
C9B—C10B	1.373 (10)	C21—H21	0.9300
C9B—C8	1.376 (10)	O22—C23	1.438 (2)
C9B—H9B	0.9300	C23—C24	1.487 (3)
C10B—C11B	1.377 (10)	C23—H23A	0.9700
C10B—H10B	0.9300	C23—H23B	0.9700
C11B—C12B	1.375 (10)	C24—C25	1.376 (3)
C11B—H11B	0.9300	C24—C29	1.379 (3)
C12B—C13B	1.377 (10)	C25—C26	1.385 (3)
C12B—H12B	0.9300	C25—H25	0.9300
C13B—C8	1.381 (10)	C26—C27	1.371 (4)
C13B—H13B	0.9300	C26—H26	0.9300
O3—C3	1.233 (2)	C27—C28	1.364 (4)
C3—C4	1.432 (3)	C27—H27	0.9300
C4—C5	1.378 (3)	C28—C29	1.367 (4)
C4—N14	1.386 (3)	C28—H28	0.9300
C5—C7	1.485 (3)	C29—H29	0.9300

C5—N1—N2B	108.1 (10)	H7A—C7—H7C	109.5
C5—N1—N2A	106.8 (4)	H7B—C7—H7C	109.5
C5—N1—C6	127.36 (19)	C9A—C8—C13A	120.3 (5)
N2B—N1—C6	124.3 (10)	C13A—C8—C9B	106.0 (10)
N2A—N1—C6	120.4 (4)	C9A—C8—C13B	135.1 (12)
C3—N2A—N1	108.5 (6)	C9B—C8—C13B	121.5 (14)
C3—N2A—C8	125.5 (6)	C9A—C8—N2B	129.3 (9)
N1—N2A—C8	118.0 (6)	C13A—C8—N2B	110.4 (10)
C8—C9A—C10A	119.5 (7)	C9B—C8—N2B	143.1 (14)
C8—C9A—H9A	120.2	C13B—C8—N2B	95.2 (14)
C10A—C9A—H9A	120.2	C9A—C8—N2A	109.0 (7)
C11A—C10A—C9A	120.4 (7)	C13A—C8—N2A	130.6 (8)
C11A—C10A—H10A	119.8	C9B—C8—N2A	123.2 (12)
C9A—C10A—H10A	119.8	C13B—C8—N2A	115.2 (12)
C12A—C11A—C10A	119.4 (6)	C15—N14—C4	120.29 (18)
C12A—C11A—H11A	120.3	N14—C15—C16	121.8 (2)
C10A—C11A—H11A	120.3	N14—C15—H15	119.1
C11A—C12A—C13A	120.5 (6)	C16—C15—H15	119.1
C11A—C12A—H12A	119.7	C21—C16—C17	117.4 (2)
C13A—C12A—H12A	119.7	C21—C16—C15	120.27 (19)
C8—C13A—C12A	119.7 (7)	C17—C16—C15	122.3 (2)
C8—C13A—H13A	120.1	C18—C17—C16	121.5 (2)
C12A—C13A—H13A	120.1	C18—C17—H17	119.2
N1—N2B—C8	122.0 (16)	C16—C17—H17	119.2
N1—N2B—C3	107.4 (15)	C17—C18—C19	120.1 (2)
C8—N2B—C3	120.1 (14)	C17—C18—H18	119.9
C10B—C9B—C8	120.7 (19)	C19—C18—H18	119.9
C10B—C9B—H9B	119.6	O22—C19—C20	126.0 (2)
C8—C9B—H9B	119.6	O22—C19—C18	114.73 (19)
C9B—C10B—C11B	115 (2)	C20—C19—C18	119.3 (2)
C9B—C10B—H10B	122.6	C19—C20—C21	119.8 (2)
C11B—C10B—H10B	122.6	C19—C20—H20	120.1
C12B—C11B—C10B	128 (2)	C21—C20—H20	120.1
C12B—C11B—H11B	116.2	C20—C21—C16	121.8 (2)
C10B—C11B—H11B	116.2	C20—C21—H21	119.1
C11B—C12B—C13B	115 (2)	C16—C21—H21	119.1
C11B—C12B—H12B	122.6	C19—O22—C23	118.30 (16)
C13B—C12B—H12B	122.6	O22—C23—C24	106.39 (16)
C12B—C13B—C8	120 (2)	O22—C23—H23A	110.5
C12B—C13B—H13B	119.8	C24—C23—H23A	110.5
C8—C13B—H13B	119.8	O22—C23—H23B	110.5
O3—C3—N2A	122.2 (4)	C24—C23—H23B	110.5
O3—C3—C4	132.8 (2)	H23A—C23—H23B	108.6
N2A—C3—C4	104.9 (4)	C25—C24—C29	118.6 (2)
O3—C3—N2B	123.0 (9)	C25—C24—C23	121.7 (2)
C4—C3—N2B	102.3 (9)	C29—C24—C23	119.7 (2)
C5—C4—N14	122.57 (19)	C24—C25—C26	120.1 (2)
C5—C4—C3	108.27 (19)	C24—C25—H25	120.0
N14—C4—C3	129.16 (19)	C26—C25—H25	120.0
N1—C5—C4	109.51 (18)	C27—C26—C25	120.2 (3)
N1—C5—C7	121.67 (19)	C27—C26—H26	119.9
C4—C5—C7	128.8 (2)	C25—C26—H26	119.9
N1—C6—H6A	109.5	C28—C27—C26	119.9 (3)
N1—C6—H6B	109.5	C28—C27—H27	120.0
H6A—C6—H6B	109.5	C26—C27—H27	120.0
N1—C6—H6C	109.5	C27—C28—C29	119.9 (3)
H6A—C6—H6C	109.5	C27—C28—H28	120.0
H6B—C6—H6C	109.5	C29—C28—H28	120.0
C5—C7—H7A	109.5	C28—C29—C24	121.3 (3)
C5—C7—H7B	109.5	C28—C29—H29	119.3
H7A—C7—H7B	109.5	C24—C29—H29	119.3
C5—C7—H7C	109.5

C5—N1—N2A—C3	14.6 (7)	C10B—C9B—C8—C9A	152 (12)
N2B—N1—N2A—C3	−82 (4)	C10B—C9B—C8—C13A	−6 (4)
C6—N1—N2A—C3	170.3 (4)	C10B—C9B—C8—C13B	−2 (5)
C5—N1—N2A—C8	165.2 (5)	C10B—C9B—C8—N2B	−176 (2)
N2B—N1—N2A—C8	68 (3)	C10B—C9B—C8—N2A	177 (2)
C6—N1—N2A—C8	−39.1 (9)	C12B—C13B—C8—C9A	−11 (6)
C8—C9A—C10A—C11A	−0.3 (18)	C12B—C13B—C8—C13A	12 (7)
C9A—C10A—C11A—C12A	−2.6 (16)	C12B—C13B—C8—C9B	−1 (6)
C10A—C11A—C12A—C13A	2.8 (16)	C12B—C13B—C8—N2B	175 (4)
C11A—C12A—C13A—C8	0 (2)	C12B—C13B—C8—N2A	179 (3)
C5—N1—N2B—C8	−165.2 (11)	N1—N2B—C8—C9A	74 (2)
N2A—N1—N2B—C8	−76 (3)	C3—N2B—C8—C9A	−66.3 (19)
C6—N1—N2B—C8	10.3 (18)	N1—N2B—C8—C13A	−106.7 (16)
C5—N1—N2B—C3	−20.5 (12)	C3—N2B—C8—C13A	112.8 (14)
N2A—N1—N2B—C3	69 (3)	N1—N2B—C8—C9B	63 (4)
C6—N1—N2B—C3	155.0 (7)	C3—N2B—C8—C9B	−77 (3)
C8—C9B—C10B—C11B	2 (5)	N1—N2B—C8—C13B	−112 (3)
C9B—C10B—C11B—C12B	2 (6)	C3—N2B—C8—C13B	108 (2)
C10B—C11B—C12B—C13B	−5 (6)	N1—N2B—C8—N2A	79 (3)
C11B—C12B—C13B—C8	4 (6)	C3—N2B—C8—N2A	−62 (3)
N1—N2A—C3—O3	170.4 (4)	C3—N2A—C8—C9A	−103.3 (10)
C8—N2A—C3—O3	22.6 (10)	N1—N2A—C8—C9A	111.6 (10)
N1—N2A—C3—C4	−13.6 (7)	C3—N2A—C8—C13A	73.6 (14)
C8—N2A—C3—C4	−161.4 (7)	N1—N2A—C8—C13A	−71.5 (13)
N1—N2A—C3—N2B	72 (3)	C3—N2A—C8—C9B	−110 (2)
C8—N2A—C3—N2B	−76 (3)	N1—N2A—C8—C9B	104 (2)
N1—N2B—C3—O3	−173.8 (6)	C3—N2A—C8—C13B	69 (3)
C8—N2B—C3—O3	−28.3 (18)	N1—N2A—C8—C13B	−76 (3)
N1—N2B—C3—N2A	−80 (3)	C3—N2A—C8—N2B	80 (3)
C8—N2B—C3—N2A	66 (3)	N1—N2A—C8—N2B	−65 (3)
N1—N2B—C3—C4	20.1 (12)	C5—C4—N14—C15	−177.2 (2)
C8—N2B—C3—C4	165.6 (12)	C3—C4—N14—C15	3.2 (4)
O3—C3—C4—C5	−176.7 (3)	C4—N14—C15—C16	178.91 (19)
N2A—C3—C4—C5	8.0 (5)	N14—C15—C16—C21	175.9 (2)
N2B—C3—C4—C5	−12.6 (8)	N14—C15—C16—C17	−3.4 (3)
O3—C3—C4—N14	3.0 (5)	C21—C16—C17—C18	0.0 (4)
N2A—C3—C4—N14	−172.3 (5)	C15—C16—C17—C18	179.3 (2)
N2B—C3—C4—N14	167.1 (8)	C16—C17—C18—C19	−1.0 (4)
N2B—N1—C5—C4	12.4 (8)	C17—C18—C19—O22	−177.9 (2)
N2A—N1—C5—C4	−9.4 (5)	C17—C18—C19—C20	1.5 (4)
C6—N1—C5—C4	−162.9 (3)	O22—C19—C20—C21	178.3 (2)
N2B—N1—C5—C7	−166.7 (8)	C18—C19—C20—C21	−0.9 (4)
N2A—N1—C5—C7	171.5 (4)	C19—C20—C21—C16	−0.1 (4)
C6—N1—C5—C7	18.0 (4)	C17—C16—C21—C20	0.5 (3)
N14—C4—C5—N1	−178.8 (2)	C15—C16—C21—C20	−178.7 (2)
C3—C4—C5—N1	1.0 (3)	C20—C19—O22—C23	−2.2 (3)
N14—C4—C5—C7	0.3 (4)	C18—C19—O22—C23	177.04 (19)
C3—C4—C5—C7	180.0 (2)	C19—O22—C23—C24	−169.24 (18)
C10A—C9A—C8—C13A	3.0 (18)	O22—C23—C24—C25	−101.5 (2)
C10A—C9A—C8—C9B	−22 (8)	O22—C23—C24—C29	76.8 (2)
C10A—C9A—C8—C13B	10 (3)	C29—C24—C25—C26	−1.0 (3)
C10A—C9A—C8—N2B	−178.0 (14)	C23—C24—C25—C26	177.3 (2)
C10A—C9A—C8—N2A	−179.7 (10)	C24—C25—C26—C27	−0.3 (4)
C12A—C13A—C8—C9A	−3 (2)	C25—C26—C27—C28	1.1 (4)
C12A—C13A—C8—C9B	4 (2)	C26—C27—C28—C29	−0.5 (4)
C12A—C13A—C8—C13B	−164 (12)	C27—C28—C29—C24	−0.8 (4)
C12A—C13A—C8—N2B	178.0 (15)	C25—C24—C29—C28	1.6 (3)
C12A—C13A—C8—N2A	−179.5 (9)	C23—C24—C29—C28	−176.8 (2)

Experimental details

Crystal data
Chemical formula	C₂₅H₂₃N₃O₂
M_r	397.46
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	13.0079 (5), 9.9079 (4), 17.0469 (9)
β (°)	103.674 (4)
V (Å³)	2134.75 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.3 × 0.2 × 0.2

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.920, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	19519, 4162, 2399
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.154, 1.03
No. of reflections	4162
No. of parameters	292
No. of restraints	12
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.15

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis PRO (Oxford Diffraction ,2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), PLATON (Spek, 2009).

Acknowledgements

RK acknowledges the Department of Science & Technology for access to the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003. BN thanks the UGC for financial assistance through the BSR one-time grant for the purchase of chemicals. PSN thanks Mangalore University for research facilities and the DST–PURSE for financial assistance.

References

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