2-(4-Isobutyl­phen­yl)-N′-[(3Z)-2-oxoindolin-3-yl­idene]propano­hydrazide

Mohamed, S.K.; Akkurt, M.; Albayati, M.R.; Singh, K.; Potgieter, H.

doi:10.1107/S160053681201269X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 4| April 2012| Pages o1222-o1223

doi:10.1107/S160053681201269X

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2-(4-Isobutylphenyl)-N′-[(3Z)-2-oxoindolin-3-ylidene]propanohydrazide

Shaaban K. Mohamed,^a Mehmet Akkurt,^b ^* Mustafa R. Albayati,^a Kuldip Singh ^c and Herman Potgieter ^d

^aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^cDepartment of Chemistry, University of Leicester, Leicester, England, and ^dSchool of Research, Enterprise & Innovation, Manchester Metropolitan University, Manchester M1 5GD, England
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 21 March 2012; accepted 23 March 2012; online 28 March 2012)

In the title compound, C₂₁H₂₃N₃O₂, the indolin-2-one group is essentially planar, with a maximum deviation of 0.016 (2) Å for the N atom, and makes a dihedral angle of 84.38 (14)° with the benzene ring. The =N—N(H)—C(=O)—C– torsion angle is 0.9 (3)°. In the crystal, molecules are linked into a three-dimensional network via N—H⋯O and C—H⋯O hydrogen bonds. In addition, a C—H⋯π interaction was observed.

Related literature

For the pharmaceutical applications of hydrazones, see: Bedia et al. (2006 ); Rollas et al. (2002 ). For the pharmaceutical applications of ibuprofen, see: Palaska et al. (2002 ). For the synthesis of hydrazones, see: Rollas & Küçükgüzel (2007 ). For some of our studies on the synthesis of biologically active compounds, see: Mohamed et al. (2012a ,b ); Soliman et al. (2012 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₁H₂₃N₃O₂
M_r = 349.42
Monoclinic, C 2/c
a = 30.366 (14) Å
b = 7.383 (3) Å
c = 21.904 (10) Å
β = 130.311 (8)°
V = 3745 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 150 K
0.35 × 0.21 × 0.10 mm

Data collection

Bruker APEX 2000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.972, T_max = 0.992
15933 measured reflections
4494 independent reflections
2050 reflections with I > 2σ(I)
R_int = 0.096

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.182
S = 0.89
4494 reflections
223 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C1/C6–C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	1.91	2.740 (4)	163
N3—H3A⋯O2ⁱⁱ	0.86	2.16	2.965 (4)	155
C5—H5⋯O2ⁱⁱ	0.93	2.30	3.218 (3)	172
C11—H11B⋯Cg1ⁱⁱⁱ	0.96	2.77	3.703 (4)	164
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y-{\script{1\over 2}}, -z+1]$ ; (iii) x, y-1, z.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681201269X/hg5199sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201269X/hg5199Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681201269X/hg5199Isup3.cml

checkCIF report

Comment top

Hydrazide-hydrazone compounds are found to be associated with various biological activities such as antimicrobial, anticonvulsant, analgesic, anti-inflammatory, antiplatelet, antitubercular and antitumor properties (Bedia et al., 2006; Rollas et al., 2002; Palaska et al., 2002; Rollas & Küçükgüzel, 2007). Further to our strategy on synthesis of biologically active compounds (Mohamed et al., 2012a,b; Soliman et al. 2012) we get interested to study the functionalization of ibuprofen moiety with the aim of synthesis of potential biologically active compounds based on the core structure of ibuprofen. The title compound (I) was synthesized on condensation of the corresponding hydrazidic acid of ibuprofen with isatin under microwave irradiation and free solvent conditions.

In the title molecule, (Fig. 1), the 1,3-dihydro-2H-indol-2-one group (O1/N1/C1—C8) which is essentially planar with a maximum deviation of -0.016 (2) Å for N1 atom, makes a dihedral angle of 84.38 (14)° with the benzene ring (C12—C17). All bond lengths and angles are within normal ranges (Allen et al., 1987). The torsion angles N2—N3—C9—C10, O2—C9—C10—C11, C15—C18—C19—C20 and C15—C18—C19—C21 are 0.9 (3), 21.8 (3), -173.2 (3) and 63.4 (4) °, respectively.

In the crystal structure, the molecules are linked by N—H···O and C—H···O intermolecular hydrogen bonds, forming a three dimensional network (Table 1 and Fig. 2). Furthermore, C—H···π interactions also play an important role in stabilizing the structure (Table 1).

Related literature top

For the pharmaceutical applications of hydrazones, see: Bedia et al. (2006); Rollas et al. (2002). For the pharmaceutical applications of ibuprofen, see: Palaska et al. (2002). For the synthesis of hydrazones, see: Rollas & Küçükgüzel (2007). For some of our studies on the synthesis of biologically active compounds, see: Mohamed et al. (2012a,b); Soliman et al. (2012). For bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of an equimolar ratio of 2-(4-isobutylphenyl)propanehydrazide (220 mg) and 1H-indole-2,3-dione (147 mg) was ground in a mortar and well mixed with few drops of acetic acid as catalytic agent. The mixture powder has been transferred in a dry conical flask then irradiated under 600 w microwave for 2–3 minutes with intervals every 30 s. The yelow solid product was collected and crystallized from ethanol to afford plate bright yellow crystals in 96% yield with m.p. at 439 - 441 K. A suitable crystals for X-ray diffraction was prepared by slow evaporation of an ethanolic solution of product over two days at room temperature.

Structure description top

For the pharmaceutical applications of hydrazones, see: Bedia et al. (2006); Rollas et al. (2002). For the pharmaceutical applications of ibuprofen, see: Palaska et al. (2002). For the synthesis of hydrazones, see: Rollas & Küçükgüzel (2007). For some of our studies on the synthesis of biologically active compounds, see: Mohamed et al. (2012a,b); Soliman et al. (2012). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
	Fig. 2. View of the crystal packing and hydrogen bonding of (I) down the b axis. H atoms not involved in hydrogen bonds have been omitted for clarity.

2-(4-Isobutylphenyl)-N'-[(3Z)-2-oxoindolin-3- ylidene]propanohydrazide top

Crystal data top

C₂₁H₂₃N₃O₂	F(000) = 1488
M_r = 349.42	D_x = 1.240 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 654 reflections
a = 30.366 (14) Å	θ = 2.9–23.4°
b = 7.383 (3) Å	µ = 0.08 mm⁻¹
c = 21.904 (10) Å	T = 150 K
β = 130.311 (8)°	Plate, yellow
V = 3745 (3) Å³	0.35 × 0.21 × 0.10 mm
Z = 8

Data collection top

Bruker APEX 2000 CCD area-detector diffractometer	4494 independent reflections
Radiation source: fine-focus sealed tube	2050 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.096
phi and ω scans	θ_max = 28.7°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −40→39
T_min = 0.972, T_max = 0.992	k = −9→9
15933 measured reflections	l = −29→28

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.182	H-atom parameters constrained
S = 0.89	w = 1/[σ²(F_o²) + (0.0771P)²] where P = (F_o² + 2F_c²)/3
4494 reflections	(Δ/σ)_max < 0.001
223 parameters	Δρ_max = 0.60 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₂₁H₂₃N₃O₂	V = 3745 (3) Å³
M_r = 349.42	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 30.366 (14) Å	µ = 0.08 mm⁻¹
b = 7.383 (3) Å	T = 150 K
c = 21.904 (10) Å	0.35 × 0.21 × 0.10 mm
β = 130.311 (8)°

Data collection top

Bruker APEX 2000 CCD area-detector diffractometer	4494 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2050 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.992	R_int = 0.096
15933 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.182	H-atom parameters constrained
S = 0.89	Δρ_max = 0.60 e Å⁻³
4494 reflections	Δρ_min = −0.39 e Å⁻³
223 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.27378 (8)	0.1979 (3)	0.28135 (11)	0.0610 (8)
O2	0.30262 (7)	−0.3536 (2)	0.51498 (11)	0.0551 (7)
N1	0.21763 (9)	0.3981 (3)	0.28414 (12)	0.0513 (8)
N2	0.26682 (8)	−0.0134 (3)	0.38256 (12)	0.0441 (7)
N3	0.26590 (8)	−0.1154 (3)	0.43261 (12)	0.0438 (7)
C1	0.19248 (10)	0.4090 (3)	0.31931 (14)	0.0449 (9)
C2	0.16039 (11)	0.5488 (4)	0.31409 (15)	0.0536 (9)
C3	0.13834 (11)	0.5291 (4)	0.35241 (16)	0.0552 (10)
C4	0.14805 (11)	0.3748 (4)	0.39497 (16)	0.0518 (10)
C5	0.18120 (10)	0.2344 (3)	0.40110 (14)	0.0462 (8)
C6	0.20363 (9)	0.2513 (3)	0.36274 (13)	0.0406 (8)
C7	0.23936 (10)	0.1382 (3)	0.35482 (14)	0.0426 (8)
C8	0.24645 (11)	0.2419 (4)	0.30246 (15)	0.0480 (9)
C9	0.30217 (10)	−0.2603 (3)	0.46825 (15)	0.0445 (8)
C10	0.34176 (10)	−0.2953 (3)	0.45024 (15)	0.0469 (9)
C11	0.36252 (12)	−0.4915 (4)	0.47037 (18)	0.0631 (11)
C12	0.39149 (10)	−0.1604 (3)	0.49514 (16)	0.0445 (9)
C13	0.43620 (11)	−0.1733 (4)	0.57647 (16)	0.0511 (10)
C14	0.48254 (11)	−0.0548 (4)	0.61611 (17)	0.0571 (10)
C15	0.48610 (12)	0.0796 (4)	0.57581 (19)	0.0556 (10)
C16	0.44102 (12)	0.0942 (4)	0.49473 (19)	0.0583 (11)
C17	0.39438 (12)	−0.0220 (4)	0.45516 (17)	0.0533 (10)
C18	0.53791 (12)	0.2047 (4)	0.6173 (2)	0.0705 (13)
C19	0.52905 (13)	0.3956 (4)	0.63358 (19)	0.0679 (7)
C20	0.58104 (12)	0.5126 (4)	0.66581 (18)	0.0679 (7)
C21	0.51718 (12)	0.3939 (4)	0.68999 (18)	0.0679 (7)
H1	0.21500	0.48110	0.25440	0.0620*
H2	0.15370	0.65350	0.28560	0.0640*
H3	0.11640	0.62220	0.34950	0.0660*
H3A	0.24300	−0.08990	0.44180	0.0530*
H4	0.13230	0.36450	0.41980	0.0620*
H5	0.18820	0.13090	0.43040	0.0550*
H10	0.31960	−0.27740	0.39270	0.0560*
H11A	0.38740	−0.51360	0.45840	0.0950*
H11B	0.32980	−0.57130	0.43910	0.0950*
H11C	0.38340	−0.51290	0.52630	0.0950*
H13	0.43530	−0.26330	0.60530	0.0610*
H14	0.51190	−0.06620	0.67120	0.0690*
H16	0.44200	0.18430	0.46600	0.0700*
H17	0.36430	−0.00710	0.40050	0.0640*
H18A	0.54900	0.21270	0.58470	0.0850*
H18B	0.56990	0.15020	0.66790	0.0850*
H19	0.49540	0.44780	0.58270	0.0810*
H20A	0.58750	0.51340	0.62830	0.1020*
H20B	0.61440	0.46460	0.71610	0.1020*
H20C	0.57410	0.63400	0.67350	0.1020*
H21A	0.48390	0.32030	0.66820	0.1020*
H21B	0.51010	0.51530	0.69750	0.1020*
H21C	0.54990	0.34500	0.74060	0.1020*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0792 (14)	0.0562 (13)	0.0671 (13)	0.0042 (10)	0.0561 (12)	−0.0018 (10)
O2	0.0503 (11)	0.0447 (11)	0.0692 (13)	0.0100 (8)	0.0381 (10)	0.0125 (10)
N1	0.0603 (14)	0.0449 (14)	0.0494 (13)	0.0086 (11)	0.0358 (12)	0.0091 (11)
N2	0.0440 (12)	0.0377 (13)	0.0491 (12)	0.0025 (10)	0.0294 (11)	−0.0028 (10)
N3	0.0415 (12)	0.0376 (12)	0.0540 (13)	0.0078 (9)	0.0316 (11)	0.0026 (10)
C1	0.0454 (15)	0.0418 (16)	0.0387 (14)	0.0060 (12)	0.0232 (13)	−0.0001 (12)
C2	0.0568 (16)	0.0387 (16)	0.0482 (16)	0.0117 (13)	0.0263 (14)	0.0041 (13)
C3	0.0562 (17)	0.0466 (17)	0.0532 (16)	0.0140 (13)	0.0311 (15)	−0.0016 (14)
C4	0.0547 (16)	0.0478 (17)	0.0545 (17)	0.0088 (13)	0.0360 (14)	−0.0005 (14)
C5	0.0448 (14)	0.0406 (15)	0.0456 (14)	0.0058 (12)	0.0258 (13)	−0.0013 (12)
C6	0.0394 (13)	0.0342 (14)	0.0396 (13)	0.0044 (11)	0.0217 (12)	−0.0016 (11)
C7	0.0417 (14)	0.0358 (14)	0.0417 (14)	0.0020 (11)	0.0231 (12)	−0.0029 (11)
C8	0.0532 (16)	0.0434 (16)	0.0435 (14)	0.0009 (13)	0.0295 (14)	−0.0058 (13)
C9	0.0387 (14)	0.0336 (14)	0.0517 (15)	0.0017 (11)	0.0250 (13)	−0.0039 (13)
C10	0.0461 (15)	0.0420 (16)	0.0503 (15)	0.0079 (12)	0.0302 (13)	−0.0044 (12)
C11	0.0606 (18)	0.0435 (18)	0.081 (2)	0.0089 (14)	0.0439 (17)	−0.0083 (15)
C12	0.0421 (14)	0.0431 (16)	0.0563 (16)	0.0105 (12)	0.0354 (14)	−0.0026 (13)
C13	0.0471 (15)	0.0458 (17)	0.0614 (18)	0.0061 (13)	0.0356 (15)	0.0005 (14)
C14	0.0444 (16)	0.0588 (19)	0.0588 (17)	0.0081 (14)	0.0292 (15)	−0.0030 (15)
C15	0.0484 (16)	0.0472 (18)	0.079 (2)	0.0078 (13)	0.0447 (17)	−0.0033 (15)
C16	0.0610 (18)	0.0468 (18)	0.081 (2)	0.0095 (14)	0.0522 (18)	0.0074 (16)
C17	0.0545 (17)	0.0521 (18)	0.0603 (17)	0.0114 (14)	0.0403 (15)	0.0012 (15)
C18	0.0526 (17)	0.058 (2)	0.104 (3)	0.0077 (15)	0.0520 (19)	−0.0014 (18)
C19	0.0653 (11)	0.0599 (12)	0.0753 (12)	0.0005 (9)	0.0441 (10)	0.0013 (10)
C20	0.0653 (11)	0.0599 (12)	0.0753 (12)	0.0005 (9)	0.0441 (10)	0.0013 (10)
C21	0.0653 (11)	0.0599 (12)	0.0753 (12)	0.0005 (9)	0.0441 (10)	0.0013 (10)

Geometric parameters (Å, º) top

O1—C8	1.227 (5)	C16—C17	1.380 (5)
O2—C9	1.227 (4)	C18—C19	1.520 (5)
N1—C1	1.394 (5)	C19—C21	1.494 (6)
N1—C8	1.343 (4)	C19—C20	1.515 (6)
N2—N3	1.345 (3)	C2—H2	0.9300
N2—C7	1.289 (3)	C3—H3	0.9300
N3—C9	1.362 (4)	C4—H4	0.9300
N1—H1	0.8600	C5—H5	0.9300
N3—H3A	0.8600	C10—H10	0.9800
C1—C6	1.399 (3)	C11—H11A	0.9600
C1—C2	1.373 (5)	C11—H11B	0.9600
C2—C3	1.379 (5)	C11—H11C	0.9600
C3—C4	1.378 (4)	C13—H13	0.9300
C4—C5	1.390 (5)	C14—H14	0.9300
C5—C6	1.388 (5)	C16—H16	0.9300
C6—C7	1.466 (4)	C17—H17	0.9300
C7—C8	1.506 (4)	C18—H18A	0.9700
C9—C10	1.510 (5)	C18—H18B	0.9700
C10—C12	1.523 (4)	C19—H19	0.9800
C10—C11	1.527 (4)	C20—H20A	0.9600
C12—C13	1.377 (4)	C20—H20B	0.9600
C12—C17	1.385 (4)	C20—H20C	0.9600
C13—C14	1.385 (5)	C21—H21A	0.9600
C14—C15	1.378 (5)	C21—H21B	0.9600
C15—C18	1.518 (5)	C21—H21C	0.9600
C15—C16	1.376 (5)

C1—N1—C8	111.6 (2)	C3—C2—H2	121.00
N3—N2—C7	121.5 (3)	C2—C3—H3	119.00
N2—N3—C9	118.1 (3)	C4—C3—H3	119.00
C8—N1—H1	124.00	C3—C4—H4	120.00
C1—N1—H1	124.00	C5—C4—H4	120.00
C9—N3—H3A	121.00	C4—C5—H5	121.00
N2—N3—H3A	121.00	C6—C5—H5	121.00
N1—C1—C2	127.6 (2)	C9—C10—H10	108.00
C2—C1—C6	121.9 (3)	C11—C10—H10	108.00
N1—C1—C6	110.5 (2)	C12—C10—H10	108.00
C1—C2—C3	117.9 (3)	C10—C11—H11A	109.00
C2—C3—C4	121.6 (3)	C10—C11—H11B	109.00
C3—C4—C5	120.5 (3)	C10—C11—H11C	109.00
C4—C5—C6	118.9 (2)	H11A—C11—H11B	110.00
C1—C6—C7	105.4 (3)	H11A—C11—H11C	109.00
C5—C6—C7	135.3 (2)	H11B—C11—H11C	109.00
C1—C6—C5	119.3 (3)	C12—C13—H13	119.00
N2—C7—C8	115.7 (3)	C14—C13—H13	119.00
C6—C7—C8	106.4 (2)	C13—C14—H14	119.00
N2—C7—C6	137.9 (3)	C15—C14—H14	119.00
O1—C8—N1	125.7 (3)	C15—C16—H16	119.00
O1—C8—C7	128.1 (3)	C17—C16—H16	119.00
N1—C8—C7	106.1 (3)	C12—C17—H17	119.00
O2—C9—N3	119.2 (3)	C16—C17—H17	119.00
N3—C9—C10	118.0 (2)	C15—C18—H18A	108.00
O2—C9—C10	122.7 (2)	C15—C18—H18B	108.00
C9—C10—C11	109.7 (3)	C19—C18—H18A	108.00
C9—C10—C12	110.1 (2)	C19—C18—H18B	108.00
C11—C10—C12	112.5 (3)	H18A—C18—H18B	107.00
C13—C12—C17	117.2 (3)	C18—C19—H19	108.00
C10—C12—C13	121.8 (3)	C20—C19—H19	108.00
C10—C12—C17	121.1 (2)	C21—C19—H19	108.00
C12—C13—C14	121.3 (3)	C19—C20—H20A	109.00
C13—C14—C15	121.5 (3)	C19—C20—H20B	109.00
C14—C15—C16	117.3 (3)	C19—C20—H20C	109.00
C14—C15—C18	122.4 (3)	H20A—C20—H20B	110.00
C16—C15—C18	120.4 (3)	H20A—C20—H20C	110.00
C15—C16—C17	121.4 (3)	H20B—C20—H20C	109.00
C12—C17—C16	121.4 (3)	C19—C21—H21A	109.00
C15—C18—C19	115.6 (4)	C19—C21—H21B	110.00
C18—C19—C21	111.1 (3)	C19—C21—H21C	110.00
C20—C19—C21	110.8 (3)	H21A—C21—H21B	109.00
C18—C19—C20	110.4 (4)	H21A—C21—H21C	109.00
C1—C2—H2	121.00	H21B—C21—H21C	109.00

C1—N1—C8—C7	0.3 (3)	C6—C7—C8—O1	179.0 (3)
C8—N1—C1—C2	179.5 (3)	C6—C7—C8—N1	0.5 (3)
C8—N1—C1—C6	−1.1 (3)	N2—C7—C8—O1	2.1 (4)
C1—N1—C8—O1	−178.2 (3)	O2—C9—C10—C11	21.8 (3)
N3—N2—C7—C8	177.3 (2)	O2—C9—C10—C12	−102.5 (3)
C7—N2—N3—C9	−171.0 (2)	N3—C9—C10—C11	−160.3 (2)
N3—N2—C7—C6	1.7 (5)	N3—C9—C10—C12	75.4 (3)
N2—N3—C9—C10	0.9 (3)	C9—C10—C12—C13	73.9 (4)
N2—N3—C9—O2	179.0 (2)	C9—C10—C12—C17	−108.0 (3)
N1—C1—C6—C7	1.4 (3)	C11—C10—C12—C13	−48.8 (4)
C2—C1—C6—C5	0.7 (4)	C11—C10—C12—C17	129.4 (3)
C2—C1—C6—C7	−179.2 (2)	C10—C12—C13—C14	177.0 (3)
N1—C1—C6—C5	−178.8 (2)	C17—C12—C13—C14	−1.2 (5)
C6—C1—C2—C3	−0.9 (4)	C10—C12—C17—C16	−176.1 (3)
N1—C1—C2—C3	178.5 (3)	C13—C12—C17—C16	2.1 (5)
C1—C2—C3—C4	0.2 (4)	C12—C13—C14—C15	−0.6 (6)
C2—C3—C4—C5	0.7 (5)	C13—C14—C15—C16	1.5 (6)
C3—C4—C5—C6	−0.9 (4)	C13—C14—C15—C18	−176.8 (4)
C4—C5—C6—C7	−180.0 (3)	C14—C15—C16—C17	−0.6 (6)
C4—C5—C6—C1	0.2 (4)	C18—C15—C16—C17	177.7 (4)
C1—C6—C7—C8	−1.2 (3)	C14—C15—C18—C19	−104.2 (4)
C5—C6—C7—C8	179.1 (3)	C16—C15—C18—C19	77.6 (5)
C5—C6—C7—N2	−5.1 (6)	C15—C16—C17—C12	−1.2 (6)
C1—C6—C7—N2	174.7 (3)	C15—C18—C19—C20	−173.2 (3)
N2—C7—C8—N1	−176.4 (2)	C15—C18—C19—C21	63.4 (4)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1/C1/C6–C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	1.91	2.740 (4)	163
N3—H3A···O2ⁱⁱ	0.86	2.16	2.965 (4)	155
C5—H5···O2ⁱⁱ	0.93	2.30	3.218 (3)	172
C11—H11B···Cg1ⁱⁱⁱ	0.96	2.77	3.703 (4)	164

Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+1/2, −y−1/2, −z+1; (iii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₃N₃O₂
M_r	349.42
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	150
a, b, c (Å)	30.366 (14), 7.383 (3), 21.904 (10)
β (°)	130.311 (8)
V (Å³)	3745 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.35 × 0.21 × 0.10

Data collection
Diffractometer	Bruker APEX 2000 CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.972, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	15933, 4494, 2050
R_int	0.096
(sin θ/λ)_max (Å⁻¹)	0.676

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.182, 0.89
No. of reflections	4494
No. of parameters	223
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.39

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1/C1/C6–C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	1.91	2.740 (4)	163
N3—H3A···O2ⁱⁱ	0.86	2.16	2.965 (4)	155
C5—H5···O2ⁱⁱ	0.93	2.30	3.218 (3)	172
C11—H11B···Cg1ⁱⁱⁱ	0.96	2.77	3.703 (4)	164

Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+1/2, −y−1/2, −z+1; (iii) x, y−1, z.

Acknowledgements

MRA gratefully thanks the Iraqi Goverment for the financial support to perform this study. Manchester Metropolitan University is acknowledged for facilitating this collaboration.

References

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Volume 68| Part 4| April 2012| Pages o1222-o1223

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