(E)-4-Amino-N′-(2-hy­droxy-5-methyl­benzyl­idene)benzohydrazide

Kargar, H.; Kia, R.; Tahir, M.N.

doi:10.1107/S1600536812027948

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Pages o2185-o2186

https://doi.org/10.1107/S1600536812027948

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(E)-4-Amino-N′-(2-hydroxy-5-methylbenzylidene)benzohydrazide

Hadi Kargar,^a ^* Reza Kia ^b ‡ and Muhammad Nawaz Tahir ^c ^*

^aDepartment of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, I. R. of IRAN, ^bDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran, and ^cDepartment of Physics, University of Sargodha, Punjab, Pakistan
^*Correspondence e-mail: h.kargar@pnu.ac.ir, dmntahir_uos@yahoo.com

(Received 9 June 2012; accepted 20 June 2012; online 23 June 2012)

The asymmetric unit of the title compound, C₁₅H₁₅N₃O₂, comprises two crystallographically independent molecules (A and B), each having an E conformation around the C=N bond. In each molecule, there is an intramolecular O—H⋯N hydrogen bond making an S(6) ring motif. The dihedral angles between the substituted phenyl rings are 17.49 (9) and 10.03 (9)°. In the crystal, N—H⋯O hydrogen bonds link neighbouring independent molecules into infinite chains, of the type –A–B–A–B–, along the a axis, enclosing R₂¹(7) ring motifs. The chains are linked by N—H⋯O hydrogen bonds and C—H⋯O interactions, leading to the formation of a three-dimensional network.

Related literature

For the coordination chemistry of Schiff base and hydrazone derivatives, see: Kucukguzel et al. (2006 ); Karthikeyan et al. (2006 ). For 4-aminobenzohydrazide-derived Schiff base structures, see: Xu (2012 ); Shi & Li (2012 ); Bakir & Green (2002 ); Kargar et al. (2012a ,b ). For standard bond lengths, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₅N₃O₂
M_r = 269.30
Triclinic, $[P \overline 1]$
a = 10.2717 (8) Å
b = 11.5668 (10) Å
c = 11.9152 (9) Å
α = 94.544 (3)°
β = 100.583 (3)°
γ = 95.880 (3)°
V = 1377.28 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 291 K
0.30 × 0.25 × 0.24 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.974, T_max = 0.979
21355 measured reflections
6081 independent reflections
3917 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.137
S = 1.05
6081 reflections
365 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N3	0.82	1.89	2.6079 (19)	145
O4—H4⋯N6	0.82	1.86	2.5826 (17)	146
N2—H1N2⋯O4ⁱ	0.94	2.01	2.9342 (18)	169
N5—H1N5⋯O1ⁱⁱ	0.95	1.93	2.8615 (17)	167
N1—H1A⋯O3ⁱⁱⁱ	0.86	2.42	3.149 (2)	142
C12—H12A⋯O3^iv	0.93	2.51	3.400 (2)	160
C17—H17A⋯O1ⁱⁱ	0.93	2.53	3.320 (2)	143
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1; (iii) x, y+1, z; (iv) x, y, z+1.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812027948/su2458sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812027948/su2458Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812027948/su2458Isup3.cml

checkCIF report

Comment top

Schiff bases are one of the most prevalent mixed-donor ligands in the field of coordination chemistry. They play an important role in the development of coordination chemistry related to catalysis and magnetism, and supramolecular architectures (Karthikeyan et al., 2006; Kucukguzel et al., 2006). Structures of Schiff bases derived from substituted 4-aminobenzohydrazide have been reported earlier (Xu, 2012; Shi & Li, 2012; Bakir & Green, 2002; Kargar et al. (2012a,b). In order to explore the structure of new Schiff base derivatives, the title compound was prepared and characterized crystallographically.

The asymmetric unit of the title compound, Fig. 1, comprises two crystallographically independent molecules (A and B) both with an E conformation around the C═N bond. The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to those reported for related structures (Xu, 2012; Shi & Li, 2012; Bakir & Green, 2002; Kargar et al. (2012a,b). In each molecule there is an intramolecular O—H···N hydrogen bond making an S(6) ring motif. The dihedral angles between the substituted phenyl rings (C1-C6/C9-C14 in molecule A and C16-C21/C24-C29 in molecule B) are 17.49 (9) and 10.03 (9)°, respectively.

In the crystal, N—H···O hydrogen bonds (Table 1 and Fig. 2) link neighbouring independent molecules into infinite chains, of the type -A-B-A-B-, along the a axis, enclosing R¹₂(7) ring motifs (Bernstein et al., 1995). The chains are linked by N-H···O hydrogen bonds and C—H···O interactions leading to the formation of a three-dimensional network (Table 1).

Related literature top

For the coordination chemistry of Schiff base and hydrazone derivatives, see: Kucukguzel et al. (2006); Karthikeyan et al. (2006). For 4-aminobenzohydrazide-derived Schiff base structures, see: Xu (2012); Shi & Li (2012); Bakir & Green (2002); Kargar et al. (2012a,b). For standard bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The title compound was synthesized by adding 1 mmol of methyl 4-aminobenzoate to a solution of 5-methylsalicylaldehyde (1 mmol) in methanol (30 ml). The mixture was refluxed with stirring for 30 min and after cooling to room temperature a light-yellow precipitate was filtered and washed with diethylether and dried in air. Yellow prismatic crystals of the title compound, suitable for X-ray structure analysis, were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days.

Structure description top

For the coordination chemistry of Schiff base and hydrazone derivatives, see: Kucukguzel et al. (2006); Karthikeyan et al. (2006). For 4-aminobenzohydrazide-derived Schiff base structures, see: Xu (2012); Shi & Li (2012); Bakir & Green (2002); Kargar et al. (2012a,b). For standard bond lengths, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 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) and PLATON (Spek, 2009).

Figures top

	Fig. 1. A view of the molecular structure of the two independent molecules of the title compound, showing 40% probability displacement ellipsoids and the atomic numbering. The intramolecular O-H···N hydrogen bonds are shown as dashed lines (see Table 1 for details).
	Fig. 2. A view along the c axis of the crystal packing of the title compound. The N—H···O hydrogen bonds and the C—H···O interactions are shown as dashed lines (see Table 1 for details; Only the H atoms involved in these interactions are shown).

(E)-4-Amino-N'-(2-hydroxy-5-methylbenzylidene)benzohydrazide top

Crystal data top

C₁₅H₁₅N₃O₂	Z = 4
M_r = 269.30	F(000) = 568
Triclinic, P1	D_x = 1.299 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2717 (8) Å	Cell parameters from 1125 reflections
b = 11.5668 (10) Å	θ = 2.5–27.4°
c = 11.9152 (9) Å	µ = 0.09 mm⁻¹
α = 94.544 (3)°	T = 291 K
β = 100.583 (3)°	Prism, yellow
γ = 95.880 (3)°	0.30 × 0.25 × 0.24 mm
V = 1377.28 (19) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6081 independent reflections
Radiation source: fine-focus sealed tube	3917 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
φ and ω scans	θ_max = 27.2°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
T_min = 0.974, T_max = 0.979	k = −14→14
21355 measured reflections	l = −15→13

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0572P)² + 0.2031P] where P = (F_o² + 2F_c²)/3
6081 reflections	(Δ/σ)_max < 0.001
365 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₅H₁₅N₃O₂	γ = 95.880 (3)°
M_r = 269.30	V = 1377.28 (19) Å³
Triclinic, P1	Z = 4
a = 10.2717 (8) Å	Mo Kα radiation
b = 11.5668 (10) Å	µ = 0.09 mm⁻¹
c = 11.9152 (9) Å	T = 291 K
α = 94.544 (3)°	0.30 × 0.25 × 0.24 mm
β = 100.583 (3)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6081 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3917 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.979	R_int = 0.028
21355 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.05	Δρ_max = 0.19 e Å⁻³
6081 reflections	Δρ_min = −0.17 e Å⁻³
365 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.41397 (14)	0.93883 (14)	0.73216 (13)	0.0416 (4)
C2	0.34820 (17)	0.95319 (16)	0.62200 (14)	0.0525 (4)
H2A	0.2819	0.8953	0.5835	0.063*
C3	0.37828 (18)	1.04928 (17)	0.56949 (15)	0.0580 (5)
H3A	0.3332	1.0558	0.4955	0.070*
C4	0.47549 (17)	1.13830 (16)	0.62444 (14)	0.0505 (4)
C5	0.54375 (16)	1.12428 (15)	0.73354 (14)	0.0507 (4)
H5A	0.6107	1.1819	0.7714	0.061*
C6	0.51343 (15)	1.02622 (15)	0.78609 (14)	0.0467 (4)
H6A	0.5604	1.0183	0.8591	0.056*
C7	0.36676 (14)	0.83795 (14)	0.78761 (13)	0.0426 (4)
C8	0.48321 (16)	0.68945 (14)	1.02368 (14)	0.0456 (4)
H8A	0.5691	0.7281	1.0467	0.055*
C9	0.43816 (16)	0.59517 (14)	1.08529 (14)	0.0446 (4)
C10	0.31463 (17)	0.52710 (15)	1.04709 (15)	0.0515 (4)
C11	0.2798 (2)	0.43601 (16)	1.10815 (19)	0.0650 (5)
H11A	0.1992	0.3889	1.0822	0.078*
C12	0.3624 (2)	0.41382 (16)	1.20672 (18)	0.0648 (5)
H12A	0.3353	0.3532	1.2473	0.078*
C13	0.4847 (2)	0.47943 (16)	1.24696 (15)	0.0584 (5)
C14	0.51992 (18)	0.56874 (15)	1.18424 (15)	0.0525 (4)
H14A	0.6023	0.6134	1.2093	0.063*
C15	0.5763 (3)	0.4523 (2)	1.35265 (18)	0.0848 (7)
H15A	0.6484	0.4149	1.3308	0.127*
H15B	0.5276	0.4011	1.3942	0.127*
H15C	0.6115	0.5234	1.4005	0.127*
C16	0.06408 (16)	0.30308 (14)	0.48957 (14)	0.0469 (4)
C17	−0.05809 (17)	0.34582 (17)	0.48283 (16)	0.0572 (5)
H17A	−0.1126	0.3465	0.4114	0.069*
C18	−0.1001 (2)	0.38722 (18)	0.57992 (17)	0.0681 (5)
H18A	−0.1829	0.4145	0.5733	0.082*
C19	−0.0209 (2)	0.38872 (19)	0.68691 (17)	0.0691 (5)
C20	0.1007 (2)	0.3453 (2)	0.69390 (17)	0.0709 (6)
H20A	0.1551	0.3446	0.7654	0.085*
C21	0.14190 (18)	0.30375 (17)	0.59809 (15)	0.0590 (5)
H21A	0.2241	0.2751	0.6053	0.071*
C22	0.11833 (16)	0.26239 (15)	0.38986 (14)	0.0466 (4)
C23	−0.00670 (15)	0.18859 (14)	0.09605 (14)	0.0458 (4)
H23A	−0.0949	0.2024	0.0929	0.055*
C24	0.03676 (15)	0.14797 (14)	−0.00741 (13)	0.0433 (4)
C25	0.16631 (15)	0.12065 (14)	−0.00588 (14)	0.0454 (4)
C26	0.20213 (17)	0.07912 (16)	−0.10588 (16)	0.0576 (5)
H26A	0.2885	0.0610	−0.1046	0.069*
C27	0.11136 (18)	0.06414 (16)	−0.20780 (16)	0.0597 (5)
H27A	0.1376	0.0364	−0.2746	0.072*
C28	−0.01883 (18)	0.08963 (16)	−0.21308 (15)	0.0557 (5)
C29	−0.05284 (16)	0.13124 (15)	−0.11215 (14)	0.0495 (4)
H29A	−0.1394	0.1490	−0.1139	0.059*
C30	−0.1168 (2)	0.0702 (2)	−0.32422 (16)	0.0785 (6)
H30A	−0.1578	0.1401	−0.3377	0.118*
H30B	−0.1841	0.0073	−0.3208	0.118*
H30C	−0.0715	0.0509	−0.3856	0.118*
N1	0.50273 (18)	1.23589 (15)	0.57157 (14)	0.0716 (5)
H1A	0.4596	1.2425	0.5038	0.086*
H1B	0.5630	1.2907	0.6060	0.086*
N2	0.45092 (13)	0.80883 (12)	0.88017 (11)	0.0473 (3)
H1N2	0.5423	0.8349	0.8962	0.057*
N3	0.40512 (13)	0.71958 (12)	0.93778 (12)	0.0474 (3)
N4	−0.0612 (2)	0.4296 (2)	0.78470 (17)	0.1166 (8)
H4A	−0.1376	0.4551	0.7801	0.140*
H4B	−0.0101	0.4297	0.8506	0.140*
N5	0.03008 (13)	0.24063 (13)	0.28828 (11)	0.0509 (4)
H1N5	−0.0634	0.2399	0.2848	0.061*
N6	0.07587 (12)	0.20552 (12)	0.19168 (11)	0.0464 (3)
O1	0.25527 (10)	0.78344 (11)	0.75600 (10)	0.0585 (3)
O2	0.22764 (12)	0.54605 (12)	0.95216 (12)	0.0704 (4)
H2	0.2591	0.6017	0.9231	0.106*
O3	0.23698 (11)	0.24990 (12)	0.39557 (10)	0.0596 (3)
O4	0.25969 (10)	0.13154 (11)	0.09292 (10)	0.0552 (3)
H4	0.2266	0.1546	0.1469	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0320 (8)	0.0510 (10)	0.0423 (9)	0.0098 (7)	0.0070 (7)	0.0025 (7)
C2	0.0493 (10)	0.0606 (11)	0.0427 (10)	0.0039 (8)	−0.0005 (8)	0.0006 (8)
C3	0.0627 (11)	0.0695 (13)	0.0394 (10)	0.0108 (9)	0.0012 (8)	0.0074 (9)
C4	0.0528 (10)	0.0540 (11)	0.0490 (10)	0.0141 (8)	0.0146 (8)	0.0099 (8)
C5	0.0425 (9)	0.0509 (10)	0.0554 (11)	0.0041 (7)	0.0035 (8)	0.0024 (8)
C6	0.0385 (8)	0.0546 (10)	0.0448 (9)	0.0091 (7)	0.0001 (7)	0.0065 (8)
C7	0.0316 (8)	0.0521 (10)	0.0436 (9)	0.0071 (7)	0.0065 (7)	−0.0001 (7)
C8	0.0412 (9)	0.0468 (9)	0.0474 (9)	−0.0015 (7)	0.0095 (7)	0.0034 (7)
C9	0.0476 (9)	0.0415 (9)	0.0466 (9)	0.0020 (7)	0.0176 (8)	0.0011 (7)
C10	0.0489 (10)	0.0495 (10)	0.0574 (11)	0.0009 (8)	0.0183 (9)	0.0002 (8)
C11	0.0615 (12)	0.0503 (11)	0.0861 (15)	−0.0065 (9)	0.0314 (11)	0.0020 (10)
C12	0.0815 (14)	0.0470 (11)	0.0766 (14)	0.0047 (10)	0.0428 (12)	0.0118 (10)
C13	0.0804 (13)	0.0466 (10)	0.0548 (11)	0.0138 (9)	0.0259 (10)	0.0076 (8)
C14	0.0581 (10)	0.0463 (10)	0.0529 (10)	0.0014 (8)	0.0132 (8)	0.0041 (8)
C15	0.122 (2)	0.0713 (14)	0.0660 (14)	0.0185 (13)	0.0191 (13)	0.0254 (11)
C16	0.0413 (9)	0.0496 (10)	0.0476 (10)	−0.0005 (7)	0.0056 (7)	0.0073 (8)
C17	0.0481 (10)	0.0683 (12)	0.0524 (11)	0.0077 (9)	0.0026 (8)	0.0037 (9)
C18	0.0568 (11)	0.0783 (14)	0.0694 (13)	0.0172 (10)	0.0118 (10)	−0.0016 (11)
C19	0.0748 (14)	0.0764 (14)	0.0577 (12)	0.0163 (11)	0.0172 (11)	−0.0033 (10)
C20	0.0685 (13)	0.0935 (16)	0.0475 (11)	0.0181 (11)	0.0021 (10)	−0.0009 (10)
C21	0.0513 (10)	0.0749 (13)	0.0485 (11)	0.0110 (9)	0.0023 (8)	0.0044 (9)
C22	0.0393 (9)	0.0522 (10)	0.0464 (10)	−0.0011 (7)	0.0042 (7)	0.0109 (8)
C23	0.0337 (8)	0.0553 (10)	0.0484 (10)	0.0044 (7)	0.0071 (7)	0.0073 (8)
C24	0.0355 (8)	0.0450 (9)	0.0474 (9)	−0.0010 (7)	0.0053 (7)	0.0064 (7)
C25	0.0357 (8)	0.0454 (9)	0.0523 (10)	−0.0022 (7)	0.0055 (7)	0.0050 (7)
C26	0.0436 (9)	0.0596 (11)	0.0700 (12)	0.0034 (8)	0.0177 (9)	−0.0029 (9)
C27	0.0588 (11)	0.0628 (12)	0.0567 (11)	−0.0015 (9)	0.0187 (9)	−0.0044 (9)
C28	0.0565 (11)	0.0569 (11)	0.0494 (10)	−0.0032 (8)	0.0057 (8)	0.0024 (8)
C29	0.0377 (8)	0.0581 (11)	0.0504 (10)	0.0030 (7)	0.0037 (7)	0.0061 (8)
C30	0.0803 (14)	0.0929 (17)	0.0531 (12)	−0.0014 (12)	0.0007 (11)	−0.0035 (11)
N1	0.0848 (12)	0.0661 (11)	0.0637 (10)	0.0052 (9)	0.0104 (9)	0.0193 (8)
N2	0.0338 (7)	0.0550 (9)	0.0521 (8)	−0.0008 (6)	0.0053 (6)	0.0145 (7)
N3	0.0425 (7)	0.0497 (8)	0.0504 (8)	−0.0001 (6)	0.0121 (7)	0.0066 (7)
N4	0.1149 (17)	0.170 (2)	0.0722 (13)	0.0597 (17)	0.0252 (12)	−0.0143 (14)
N5	0.0348 (7)	0.0746 (10)	0.0412 (8)	0.0023 (6)	0.0060 (6)	0.0026 (7)
N6	0.0358 (7)	0.0556 (9)	0.0475 (8)	0.0006 (6)	0.0083 (6)	0.0077 (6)
O1	0.0343 (6)	0.0699 (8)	0.0650 (8)	−0.0040 (5)	−0.0003 (5)	0.0048 (6)
O2	0.0516 (7)	0.0749 (10)	0.0781 (9)	−0.0115 (6)	0.0052 (7)	0.0092 (7)
O3	0.0382 (7)	0.0875 (9)	0.0533 (7)	0.0084 (6)	0.0064 (5)	0.0136 (6)
O4	0.0332 (6)	0.0699 (8)	0.0591 (8)	0.0054 (5)	0.0015 (5)	0.0041 (6)

Geometric parameters (Å, º) top

C1—C6	1.387 (2)	C18—C19	1.378 (3)
C1—C2	1.392 (2)	C18—H18A	0.9300
C1—C7	1.469 (2)	C19—N4	1.372 (3)
C2—C3	1.354 (2)	C19—C20	1.384 (3)
C2—H2A	0.9300	C20—C21	1.359 (3)
C3—C4	1.389 (2)	C20—H20A	0.9300
C3—H3A	0.9300	C21—H21A	0.9300
C4—N1	1.365 (2)	C22—O3	1.2320 (19)
C4—C5	1.389 (2)	C22—N5	1.361 (2)
C5—C6	1.374 (2)	C23—N6	1.2773 (19)
C5—H5A	0.9300	C23—C24	1.447 (2)
C6—H6A	0.9300	C23—H23A	0.9300
C7—O1	1.2274 (18)	C24—C29	1.395 (2)
C7—N2	1.3585 (19)	C24—C25	1.396 (2)
C8—N3	1.2745 (19)	C25—O4	1.3633 (18)
C8—C9	1.446 (2)	C25—C26	1.376 (2)
C8—H8A	0.9300	C26—C27	1.375 (2)
C9—C14	1.391 (2)	C26—H26A	0.9300
C9—C10	1.401 (2)	C27—C28	1.390 (3)
C10—O2	1.354 (2)	C27—H27A	0.9300
C10—C11	1.381 (3)	C28—C29	1.377 (2)
C11—C12	1.375 (3)	C28—C30	1.495 (2)
C11—H11A	0.9300	C29—H29A	0.9300
C12—C13	1.382 (3)	C30—H30A	0.9600
C12—H12A	0.9300	C30—H30B	0.9600
C13—C14	1.379 (2)	C30—H30C	0.9600
C13—C15	1.503 (3)	N1—H1A	0.8600
C14—H14A	0.9300	N1—H1B	0.8600
C15—H15A	0.9600	N2—N3	1.3746 (18)
C15—H15B	0.9600	N2—H1N2	0.9357
C15—H15C	0.9600	N4—H4A	0.8600
C16—C17	1.386 (2)	N4—H4B	0.8600
C16—C21	1.389 (2)	N5—N6	1.3693 (18)
C16—C22	1.467 (2)	N5—H1N5	0.9526
C17—C18	1.375 (3)	O2—H2	0.8200
C17—H17A	0.9300	O4—H4	0.8200

C6—C1—C2	117.47 (15)	C19—C18—H18A	119.6
C6—C1—C7	123.98 (14)	N4—C19—C18	121.6 (2)
C2—C1—C7	118.34 (14)	N4—C19—C20	120.3 (2)
C3—C2—C1	121.66 (16)	C18—C19—C20	118.12 (18)
C3—C2—H2A	119.2	C21—C20—C19	121.11 (18)
C1—C2—H2A	119.2	C21—C20—H20A	119.4
C2—C3—C4	120.99 (16)	C19—C20—H20A	119.4
C2—C3—H3A	119.5	C20—C21—C16	121.48 (18)
C4—C3—H3A	119.5	C20—C21—H21A	119.3
N1—C4—C3	120.40 (16)	C16—C21—H21A	119.3
N1—C4—C5	121.57 (17)	O3—C22—N5	120.98 (16)
C3—C4—C5	118.03 (16)	O3—C22—C16	122.88 (15)
C6—C5—C4	120.71 (16)	N5—C22—C16	116.13 (14)
C6—C5—H5A	119.6	N6—C23—C24	120.07 (14)
C4—C5—H5A	119.6	N6—C23—H23A	120.0
C5—C6—C1	121.12 (15)	C24—C23—H23A	120.0
C5—C6—H6A	119.4	C29—C24—C25	117.95 (15)
C1—C6—H6A	119.4	C29—C24—C23	120.09 (14)
O1—C7—N2	120.24 (15)	C25—C24—C23	121.93 (14)
O1—C7—C1	122.84 (14)	O4—C25—C26	118.01 (14)
N2—C7—C1	116.88 (13)	O4—C25—C24	122.05 (15)
N3—C8—C9	119.98 (15)	C26—C25—C24	119.92 (15)
N3—C8—H8A	120.0	C27—C26—C25	120.60 (16)
C9—C8—H8A	120.0	C27—C26—H26A	119.7
C14—C9—C10	118.37 (15)	C25—C26—H26A	119.7
C14—C9—C8	119.70 (15)	C26—C27—C28	121.37 (17)
C10—C9—C8	121.92 (15)	C26—C27—H27A	119.3
O2—C10—C11	118.23 (16)	C28—C27—H27A	119.3
O2—C10—C9	122.92 (16)	C29—C28—C27	117.21 (16)
C11—C10—C9	118.84 (17)	C29—C28—C30	122.23 (18)
C12—C11—C10	121.07 (18)	C27—C28—C30	120.55 (18)
C12—C11—H11A	119.5	C28—C29—C24	122.95 (16)
C10—C11—H11A	119.5	C28—C29—H29A	118.5
C11—C12—C13	121.56 (18)	C24—C29—H29A	118.5
C11—C12—H12A	119.2	C28—C30—H30A	109.5
C13—C12—H12A	119.2	C28—C30—H30B	109.5
C14—C13—C12	116.99 (18)	H30A—C30—H30B	109.5
C14—C13—C15	121.74 (19)	C28—C30—H30C	109.5
C12—C13—C15	121.25 (18)	H30A—C30—H30C	109.5
C13—C14—C9	123.14 (17)	H30B—C30—H30C	109.5
C13—C14—H14A	118.4	C4—N1—H1A	120.0
C9—C14—H14A	118.4	C4—N1—H1B	120.0
C13—C15—H15A	109.5	H1A—N1—H1B	120.0
C13—C15—H15B	109.5	C7—N2—N3	117.71 (13)
H15A—C15—H15B	109.5	C7—N2—H1N2	122.5
C13—C15—H15C	109.5	N3—N2—H1N2	118.4
H15A—C15—H15C	109.5	C8—N3—N2	118.76 (13)
H15B—C15—H15C	109.5	C19—N4—H4A	120.0
C17—C16—C21	117.31 (16)	C19—N4—H4B	120.0
C17—C16—C22	124.35 (15)	H4A—N4—H4B	120.0
C21—C16—C22	118.28 (15)	C22—N5—N6	118.69 (13)
C18—C17—C16	121.16 (17)	C22—N5—H1N5	121.4
C18—C17—H17A	119.4	N6—N5—H1N5	119.5
C16—C17—H17A	119.4	C23—N6—N5	118.36 (13)
C17—C18—C19	120.81 (18)	C10—O2—H2	109.5
C17—C18—H18A	119.6	C25—O4—H4	109.5

C6—C1—C2—C3	−0.9 (2)	C17—C18—C19—C20	−1.3 (3)
C7—C1—C2—C3	174.06 (16)	N4—C19—C20—C21	179.6 (2)
C1—C2—C3—C4	−0.7 (3)	C18—C19—C20—C21	0.9 (3)
C2—C3—C4—N1	−178.50 (17)	C19—C20—C21—C16	0.0 (3)
C2—C3—C4—C5	1.9 (3)	C17—C16—C21—C20	−0.4 (3)
N1—C4—C5—C6	178.96 (16)	C22—C16—C21—C20	176.92 (18)
C3—C4—C5—C6	−1.4 (3)	C17—C16—C22—O3	163.12 (17)
C4—C5—C6—C1	−0.2 (3)	C21—C16—C22—O3	−14.1 (3)
C2—C1—C6—C5	1.3 (2)	C17—C16—C22—N5	−15.7 (2)
C7—C1—C6—C5	−173.31 (15)	C21—C16—C22—N5	167.10 (15)
C6—C1—C7—O1	155.69 (16)	N6—C23—C24—C29	−178.99 (15)
C2—C1—C7—O1	−18.9 (2)	N6—C23—C24—C25	3.2 (2)
C6—C1—C7—N2	−21.9 (2)	C29—C24—C25—O4	−178.41 (14)
C2—C1—C7—N2	163.53 (14)	C23—C24—C25—O4	−0.5 (2)
N3—C8—C9—C14	−174.96 (15)	C29—C24—C25—C26	0.3 (2)
N3—C8—C9—C10	6.4 (2)	C23—C24—C25—C26	178.13 (16)
C14—C9—C10—O2	179.69 (16)	O4—C25—C26—C27	178.73 (15)
C8—C9—C10—O2	−1.6 (3)	C24—C25—C26—C27	0.0 (3)
C14—C9—C10—C11	−0.8 (2)	C25—C26—C27—C28	−0.4 (3)
C8—C9—C10—C11	177.92 (16)	C26—C27—C28—C29	0.4 (3)
O2—C10—C11—C12	−178.53 (17)	C26—C27—C28—C30	−178.63 (17)
C9—C10—C11—C12	1.9 (3)	C27—C28—C29—C24	−0.1 (3)
C10—C11—C12—C13	−1.8 (3)	C30—C28—C29—C24	178.90 (17)
C11—C12—C13—C14	0.4 (3)	C25—C24—C29—C28	−0.2 (2)
C11—C12—C13—C15	−178.03 (18)	C23—C24—C29—C28	−178.10 (16)
C12—C13—C14—C9	0.7 (3)	O1—C7—N2—N3	−1.8 (2)
C15—C13—C14—C9	179.17 (17)	C1—C7—N2—N3	175.79 (13)
C10—C9—C14—C13	−0.5 (3)	C9—C8—N3—N2	−179.45 (14)
C8—C9—C14—C13	−179.26 (16)	C7—N2—N3—C8	178.80 (14)
C21—C16—C17—C18	0.0 (3)	O3—C22—N5—N6	−0.6 (2)
C22—C16—C17—C18	−177.14 (17)	C16—C22—N5—N6	178.23 (14)
C16—C17—C18—C19	0.8 (3)	C24—C23—N6—N5	−178.08 (14)
C17—C18—C19—N4	−179.9 (2)	C22—N5—N6—C23	−177.96 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N3	0.82	1.89	2.6079 (19)	145
O4—H4···N6	0.82	1.86	2.5826 (17)	146
N2—H1N2···O4ⁱ	0.94	2.01	2.9342 (18)	169
N5—H1N5···O1ⁱⁱ	0.95	1.93	2.8615 (17)	167
N1—H1A···O3ⁱⁱⁱ	0.86	2.42	3.149 (2)	142
C12—H12A···O3^iv	0.93	2.51	3.400 (2)	160
C17—H17A···O1ⁱⁱ	0.93	2.53	3.320 (2)	143

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1; (iii) x, y+1, z; (iv) x, y, z+1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅N₃O₂
M_r	269.30
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	10.2717 (8), 11.5668 (10), 11.9152 (9)
α, β, γ (°)	94.544 (3), 100.583 (3), 95.880 (3)
V (Å³)	1377.28 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.25 × 0.24

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.974, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	21355, 6081, 3917
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.642

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.137, 1.05
No. of reflections	6081
No. of parameters	365
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.17

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N3	0.82	1.89	2.6079 (19)	145
O4—H4···N6	0.82	1.86	2.5826 (17)	146
N2—H1N2···O4ⁱ	0.94	2.01	2.9342 (18)	169
N5—H1N5···O1ⁱⁱ	0.95	1.93	2.8615 (17)	167
N1—H1A···O3ⁱⁱⁱ	0.86	2.42	3.149 (2)	142
C12—H12A···O3^iv	0.93	2.51	3.400 (2)	160
C17—H17A···O1ⁱⁱ	0.93	2.53	3.320 (2)	143

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1; (iii) x, y+1, z; (iv) x, y, z+1.

Footnotes

‡Present address: Structural Dynamics of (Bio)Chemical Systems, Max Planck Institute for Biophysical Chemistry, Am Fassberg 11, 37077 Göttingen, Germany.

Acknowledgements

HK thanks PNU for financial support. MNT thanks GC University of Sargodha, Pakistan, for the research facility.

References

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