2-(5,6-Dihydro­benzimidazo[1,2-c]quinazolin-6-yl)-5-meth­oxy­phenol

Eltayeb, N.E.; Teoh, S.G.; Chantrapromma, S.; Fun, H.-K.

doi:10.1107/S1600536811034027

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 9| September 2011| Pages o2410-o2411

doi:10.1107/S1600536811034027

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2-(5,6-Dihydrobenzimidazo[1,2-c]quinazolin-6-yl)-5-methoxyphenol

Naser Eltaher Eltayeb,^a,^b Siang Guan Teoh,^a Suchada Chantrapromma ^c ‡ and Hoong-Kun Fun ^d ^*§

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Chemistry, Faculty of Pure and Applied Sciences, International University of Africa, Sudan, ^cCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 16 August 2011; accepted 19 August 2011; online 27 August 2011)

In the title quinazoline derivative, C₂₁H₁₇N₃O₂, the benzimidazole unit makes dihedral angles of 8.29 (5) and 81.79 (5)° with the benzene rings of the quinazoline and methoxyphenol units, respectively. The nitrogen-containing six-membered ring adopts a half-chair conformation. In the crystal, the molecules are linked through O—H⋯N hydrogen bonds into screw chains along the b axis; adjacent chains are further connected by N—H⋯O hydrogen bonds, thereby forming a two-dimensional network lying parallel to the bc plane. Weak C—H⋯π and π⋯π interactions with centroid–centroid distances of 3.5258 (8) and 3.7184 (7) Å are present and N⋯O [2.6816 (15) and 3.0519 (15) Å] short contacts also occur.

Related literature

For background to benzoheterocyclic derivatives and their applications, see: Arienzo et al. (2007 ); Chassaing et al. (2008 ); Galarcei et al. (2008 ); Kumar & Rajput (2009 ); Kung et al. (2009 ); Podunavac-Kuzmanovic & Cvetkovic (2010 ); Via et al. (2001 ); Xue et al. (2011 ); Zhang et al. (2009 ). For related structures, see: Eltayeb et al. (2007 , 2009 , 2011a ,b ). For reference bond-length data, see: Allen et al. (1987 ). For ring conformations, see: Cremer & Pople (1975 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₁H₁₇N₃O₂
M_r = 343.38
Monoclinic, P 2₁ /c
a = 9.5408 (1) Å
b = 15.6503 (2) Å
c = 11.7609 (1) Å
β = 110.408 (1)°
V = 1645.87 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.28 × 0.25 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.974, T_max = 0.980
31713 measured reflections
6610 independent reflections
4637 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.139
S = 1.05
6610 reflections
244 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C15–C20 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N3⋯O2ⁱ	0.907 (19)	2.211 (19)	3.0519 (15)	153.8 (17)
O1—H1O1⋯N2ⁱⁱ	0.98 (2)	1.72 (2)	2.6816 (15)	168 (2)
C2—H2A⋯Cg4	0.95	2.85	3.6277 (16)	140
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811034027/hb6371sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811034027/hb6371Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811034027/hb6371Isup3.cml

checkCIF report

Comment top

Benzoheterocyclic derivatives have been used widely in the pharmaceutical industry and medicine due to their diverse pharmaceutical activities (Arienzo et al., 2007; Chassaing et al., 2008; Kumar et al., 2009; Kung et al., 2009; Podunavac-Kuzmanovic & Cvetkovic, 2010; Zhang et al., 2009) including inhibition against enteroviruses (Xue et al., 2011) and potent antitumor activity (Galarcei et al., 2008; Via et al., 2001). Due to their interesting activities, the benzimidazole and quinazoline scaffolds were selected for our ongoing structural studies (Eltayeb et al., 2007; 2009; 2011a; 2011b).

In the title compound (I) (Fig. 1), the benzimidazole ring system (C1–C7/N1–N2) is planar with the r.m.s. of 0.0086 (1) Å with the most deviation for atom C1 of 0.0183 (1) Å. The benzimidazole makes the dihedral angle of 8.29 (5)° with the C8–C13 benzene ring of the quinazoline moiety (C7–C14/N1/N3). The nitrogen six-membered ring adopts a half-chair conformation with the puckering parameter Q = 0.3941 (13) Å, θ = 59.34 (19)° and ϕ = 277.7 (2)° (Cremer & Pople, 1975). The orientation of the 5-methoxyphenol can be indicated by the dihedral angle between the phenol ring and benzimidazole of 81.79 (5)°. The methoxy substituted is slightly twisted from its attached benzene ring with the torsion angle C21–O2–C18–C19 = 8.93 (17)°. The bond lengths agree with the literature values (Allen et al., 1987).

In the crystal structure of (I) as shown Fig. 2, the molecules are linked through O—H···N hydrogen bonds (Table 1) into screw chains along the b axis. The adjacent screw chains are further connected by N—H···O hydrogen bonds (Table 1) forming the two-dimensional network parallel to the bc plane. The crystal is further stabilized by C—H···π weak interactions (Table 1). π···π interactions were also observed with centroid···centroid distances: Cg₁···Cg₃ⁱⁱⁱ = 3.7184 (7) Å and Cg₂···Cg₂^iv = 3.5258 (8) Å; Cg₁, Cg₂ and Cg₃ are the centroids of C1/C6/C7/N1–N2, C1–C6 and C8–C13 rings, respectively (symmetry codes: (iii) = -x, 1-y, -z and (iv) = -x, 1-y 1-z). N···O[2.6816 (15) and 3.0519 (15) Å] short contacts were also observed.

Related literature top

For background to benzoheterocyclic derivatives and their applications, see: Arienzo et al. (2007); Chassaing et al. (2008); Galarcei et al. (2008); Kumar et al. (2009); Kung et al. (2009); Podunavac-Kuzmanovic & Cvetkovic (2010); Via et al. (2001); Xue et al. (2011); Zhang et al. (2009). For related structures, see: Eltayeb et al. (2007, 2009, 2011a,b). For reference bond-length data, see: Allen et al. (1987). For ring conformations, see Cremer & Pople (1975). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986).

Experimental top

The title compound was synthesized by adding 2-hydroxy-4-methoxybenzaldehyde (0.304 g, 2.0 mmol) to a solution of 2-(2-aminophenyl)-1H-benzimidazole (0.418 g, 2.0 mmol) in ethanol (30 mL). The mixture was refluxed with stirring for 2 hrs. The color of the resulting solution was pale-yellow. Pale-yellow blocks were formed after three weeks of slow evaporation of ethanol at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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. The molecular structure of the title compound, with 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound viewed down the a axis, showing 2D network parallel to the bc plane. Hydrogen bonds are shown as dashed lines.

2-(5,6-dihydrobenzimidazo[1,2-c]quinazolin-6-yl)-5-methoxyphenol top

Crystal data top

C₂₁H₁₇N₃O₂	F(000) = 720
M_r = 343.38	D_x = 1.386 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6610 reflections
a = 9.5408 (1) Å	θ = 2.3–33.8°
b = 15.6503 (2) Å	µ = 0.09 mm⁻¹
c = 11.7609 (1) Å	T = 100 K
β = 110.408 (1)°	Block, pale yellow
V = 1645.87 (3) Å³	0.28 × 0.25 × 0.22 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	6610 independent reflections
Radiation source: sealed tube	4637 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ϕ and ω scans	θ_max = 33.8°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −14→14
T_min = 0.974, T_max = 0.980	k = −24→22
31713 measured reflections	l = −18→18

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0535P)² + 0.6883P] where P = (F_o² + 2F_c²)/3
6610 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₁H₁₇N₃O₂	V = 1645.87 (3) Å³
M_r = 343.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.5408 (1) Å	µ = 0.09 mm⁻¹
b = 15.6503 (2) Å	T = 100 K
c = 11.7609 (1) Å	0.28 × 0.25 × 0.22 mm
β = 110.408 (1)°

Data collection top

Bruker APEXII CCD diffractometer	6610 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4637 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.980	R_int = 0.039
31713 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.43 e Å⁻³
6610 reflections	Δρ_min = −0.30 e Å⁻³
244 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K.

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
O1	0.14755 (11)	0.22525 (6)	0.27396 (8)	0.0225 (2)
O2	0.48793 (10)	0.20256 (6)	0.67860 (8)	0.01967 (19)
N1	0.09967 (11)	0.45602 (7)	0.26995 (9)	0.0155 (2)
N2	−0.06837 (12)	0.56241 (7)	0.21091 (10)	0.0195 (2)
N3	0.32315 (12)	0.45264 (7)	0.22680 (10)	0.0181 (2)
C1	−0.00334 (14)	0.44114 (8)	0.32723 (11)	0.0169 (2)
C2	−0.01453 (15)	0.37959 (9)	0.40964 (12)	0.0214 (3)
H2A	0.0559	0.3344	0.4361	0.026*
C3	−0.13327 (16)	0.38755 (9)	0.45104 (13)	0.0261 (3)
H3A	−0.1438	0.3471	0.5078	0.031*
C4	−0.23825 (16)	0.45360 (10)	0.41148 (14)	0.0276 (3)
H4A	−0.3193	0.4562	0.4407	0.033*
C5	−0.22662 (15)	0.51499 (9)	0.33108 (13)	0.0251 (3)
H5A	−0.2975	0.5600	0.3051	0.030*
C6	−0.10683 (14)	0.50852 (8)	0.28924 (11)	0.0185 (2)
C7	0.05266 (14)	0.52788 (8)	0.19987 (11)	0.0165 (2)
C8	0.13443 (14)	0.55651 (8)	0.12348 (11)	0.0170 (2)
C9	0.08353 (15)	0.62216 (8)	0.03824 (11)	0.0206 (3)
H9A	−0.0070	0.6510	0.0303	0.025*
C10	0.16415 (16)	0.64543 (9)	−0.03470 (11)	0.0230 (3)
H10A	0.1282	0.6894	−0.0935	0.028*
C11	0.29812 (16)	0.60404 (9)	−0.02133 (11)	0.0233 (3)
H11A	0.3534	0.6199	−0.0713	0.028*
C12	0.35181 (16)	0.53980 (9)	0.06425 (11)	0.0209 (3)
H12A	0.4444	0.5128	0.0737	0.025*
C13	0.26941 (14)	0.51475 (8)	0.13664 (11)	0.0171 (2)
C14	0.21403 (13)	0.39827 (8)	0.25378 (10)	0.0157 (2)
H14A	0.1659	0.3593	0.1836	0.019*
C15	0.29119 (13)	0.34584 (8)	0.36554 (10)	0.0148 (2)
C16	0.25404 (13)	0.25964 (8)	0.37158 (11)	0.0159 (2)
C17	0.32374 (13)	0.21322 (8)	0.47774 (10)	0.0162 (2)
H17A	0.2994	0.1547	0.4821	0.019*
C18	0.42921 (13)	0.25281 (8)	0.57752 (10)	0.0154 (2)
C19	0.46985 (14)	0.33780 (8)	0.57194 (11)	0.0171 (2)
H19A	0.5438	0.3643	0.6389	0.021*
C20	0.39884 (13)	0.38268 (8)	0.46523 (11)	0.0163 (2)
H20A	0.4251	0.4408	0.4605	0.020*
C21	0.57945 (16)	0.24524 (10)	0.78736 (12)	0.0258 (3)
H21A	0.6014	0.2060	0.8563	0.039*
H21B	0.5261	0.2953	0.8016	0.039*
H21C	0.6733	0.2635	0.7783	0.039*
H1N3	0.3958 (19)	0.4194 (12)	0.2166 (15)	0.028 (4)*
H1O1	0.126 (2)	0.1665 (15)	0.291 (2)	0.059 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0248 (5)	0.0166 (5)	0.0191 (4)	−0.0058 (4)	−0.0014 (4)	0.0006 (3)
O2	0.0217 (4)	0.0185 (4)	0.0154 (4)	−0.0019 (4)	0.0021 (3)	0.0027 (3)
N1	0.0152 (5)	0.0139 (5)	0.0175 (4)	0.0018 (4)	0.0059 (4)	0.0019 (4)
N2	0.0190 (5)	0.0167 (5)	0.0214 (5)	0.0031 (4)	0.0054 (4)	0.0003 (4)
N3	0.0185 (5)	0.0166 (5)	0.0214 (5)	0.0033 (4)	0.0098 (4)	0.0042 (4)
C1	0.0155 (5)	0.0172 (6)	0.0180 (5)	−0.0007 (4)	0.0057 (4)	−0.0019 (4)
C2	0.0211 (6)	0.0196 (6)	0.0253 (6)	0.0019 (5)	0.0103 (5)	0.0025 (5)
C3	0.0277 (7)	0.0241 (7)	0.0316 (7)	−0.0024 (6)	0.0166 (6)	0.0014 (5)
C4	0.0239 (7)	0.0271 (7)	0.0378 (8)	−0.0020 (6)	0.0184 (6)	−0.0052 (6)
C5	0.0201 (6)	0.0220 (7)	0.0345 (7)	0.0032 (5)	0.0113 (5)	−0.0031 (5)
C6	0.0168 (6)	0.0164 (6)	0.0214 (5)	0.0010 (5)	0.0054 (4)	−0.0025 (4)
C7	0.0175 (5)	0.0130 (5)	0.0165 (5)	0.0007 (4)	0.0028 (4)	−0.0004 (4)
C8	0.0203 (6)	0.0133 (5)	0.0160 (5)	−0.0011 (4)	0.0048 (4)	−0.0005 (4)
C9	0.0243 (6)	0.0156 (6)	0.0185 (5)	−0.0002 (5)	0.0031 (5)	0.0011 (4)
C10	0.0311 (7)	0.0169 (6)	0.0169 (5)	−0.0034 (5)	0.0034 (5)	0.0021 (4)
C11	0.0313 (7)	0.0207 (6)	0.0181 (5)	−0.0069 (5)	0.0091 (5)	−0.0005 (5)
C12	0.0244 (6)	0.0194 (6)	0.0201 (6)	−0.0012 (5)	0.0094 (5)	−0.0002 (5)
C13	0.0215 (6)	0.0134 (5)	0.0160 (5)	−0.0015 (4)	0.0061 (4)	−0.0002 (4)
C14	0.0170 (5)	0.0134 (5)	0.0170 (5)	0.0017 (4)	0.0063 (4)	0.0006 (4)
C15	0.0150 (5)	0.0127 (5)	0.0173 (5)	0.0009 (4)	0.0064 (4)	0.0009 (4)
C16	0.0144 (5)	0.0154 (5)	0.0166 (5)	0.0001 (4)	0.0039 (4)	−0.0002 (4)
C17	0.0173 (5)	0.0126 (5)	0.0181 (5)	−0.0005 (4)	0.0056 (4)	0.0010 (4)
C18	0.0145 (5)	0.0162 (6)	0.0155 (5)	0.0014 (4)	0.0053 (4)	0.0013 (4)
C19	0.0169 (5)	0.0164 (6)	0.0173 (5)	−0.0027 (4)	0.0049 (4)	−0.0024 (4)
C20	0.0171 (5)	0.0124 (5)	0.0202 (5)	−0.0012 (4)	0.0077 (4)	−0.0003 (4)
C21	0.0268 (7)	0.0277 (7)	0.0165 (5)	−0.0066 (6)	−0.0005 (5)	0.0030 (5)

Geometric parameters (Å, º) top

O1—C16	1.3516 (14)	C8—C13	1.4038 (18)
O1—H1O1	0.98 (2)	C9—C10	1.386 (2)
O2—C18	1.3716 (14)	C9—H9A	0.9500
O2—C21	1.4373 (15)	C10—C11	1.392 (2)
N1—C7	1.3739 (15)	C10—H10A	0.9500
N1—C1	1.3913 (16)	C11—C12	1.3880 (18)
N1—C14	1.4793 (15)	C11—H11A	0.9500
N2—C7	1.3217 (17)	C12—C13	1.4012 (18)
N2—C6	1.3894 (17)	C12—H12A	0.9500
N3—C13	1.3974 (16)	C14—C15	1.5060 (16)
N3—C14	1.4626 (16)	C14—H14A	1.0000
N3—H1N3	0.908 (18)	C15—C20	1.3863 (16)
C1—C2	1.3967 (18)	C15—C16	1.4030 (17)
C1—C6	1.4067 (18)	C16—C17	1.3964 (16)
C2—C3	1.3859 (19)	C17—C18	1.3964 (17)
C2—H2A	0.9500	C17—H17A	0.9500
C3—C4	1.401 (2)	C18—C19	1.3934 (17)
C3—H3A	0.9500	C19—C20	1.3909 (17)
C4—C5	1.379 (2)	C19—H19A	0.9500
C4—H4A	0.9500	C20—H20A	0.9500
C5—C6	1.3967 (19)	C21—H21A	0.9800
C5—H5A	0.9500	C21—H21B	0.9800
C7—C8	1.4509 (18)	C21—H21C	0.9800
C8—C9	1.3989 (17)

C16—O1—H1O1	110.2 (13)	C12—C11—C10	120.74 (13)
C18—O2—C21	116.28 (10)	C12—C11—H11A	119.6
C7—N1—C1	106.83 (10)	C10—C11—H11A	119.6
C7—N1—C14	121.61 (10)	C11—C12—C13	119.99 (13)
C1—N1—C14	129.58 (10)	C11—C12—H12A	120.0
C7—N2—C6	105.00 (10)	C13—C12—H12A	120.0
C13—N3—C14	117.95 (10)	N3—C13—C12	121.37 (12)
C13—N3—H1N3	113.2 (11)	N3—C13—C8	119.16 (11)
C14—N3—H1N3	109.2 (11)	C12—C13—C8	119.36 (11)
N1—C1—C2	133.57 (12)	N3—C14—N1	106.57 (10)
N1—C1—C6	104.88 (11)	N3—C14—C15	109.75 (10)
C2—C1—C6	121.49 (12)	N1—C14—C15	112.25 (9)
C3—C2—C1	116.84 (12)	N3—C14—H14A	109.4
C3—C2—H2A	121.6	N1—C14—H14A	109.4
C1—C2—H2A	121.6	C15—C14—H14A	109.4
C2—C3—C4	121.79 (13)	C20—C15—C16	118.87 (11)
C2—C3—H3A	119.1	C20—C15—C14	120.27 (11)
C4—C3—H3A	119.1	C16—C15—C14	120.85 (10)
C5—C4—C3	121.50 (13)	O1—C16—C17	122.33 (11)
C5—C4—H4A	119.3	O1—C16—C15	117.93 (11)
C3—C4—H4A	119.3	C17—C16—C15	119.71 (11)
C4—C5—C6	117.53 (13)	C16—C17—C18	119.96 (11)
C4—C5—H5A	121.2	C16—C17—H17A	120.0
C6—C5—H5A	121.2	C18—C17—H17A	120.0
N2—C6—C5	128.86 (12)	O2—C18—C19	123.50 (11)
N2—C6—C1	110.31 (11)	O2—C18—C17	115.52 (11)
C5—C6—C1	120.83 (12)	C19—C18—C17	120.98 (11)
N2—C7—N1	112.91 (11)	C20—C19—C18	117.94 (11)
N2—C7—C8	127.69 (11)	C20—C19—H19A	121.0
N1—C7—C8	119.39 (11)	C18—C19—H19A	121.0
C9—C8—C13	119.79 (12)	C15—C20—C19	122.49 (11)
C9—C8—C7	122.91 (12)	C15—C20—H20A	118.8
C13—C8—C7	117.30 (11)	C19—C20—H20A	118.8
C10—C9—C8	120.52 (13)	O2—C21—H21A	109.5
C10—C9—H9A	119.7	O2—C21—H21B	109.5
C8—C9—H9A	119.7	H21A—C21—H21B	109.5
C9—C10—C11	119.58 (12)	O2—C21—H21C	109.5
C9—C10—H10A	120.2	H21A—C21—H21C	109.5
C11—C10—H10A	120.2	H21B—C21—H21C	109.5

C7—N1—C1—C2	−178.82 (14)	C14—N3—C13—C8	35.42 (16)
C14—N1—C1—C2	17.3 (2)	C11—C12—C13—N3	−177.47 (12)
C7—N1—C1—C6	−1.59 (13)	C11—C12—C13—C8	−1.42 (19)
C14—N1—C1—C6	−165.47 (11)	C9—C8—C13—N3	176.42 (11)
N1—C1—C2—C3	177.56 (13)	C7—C8—C13—N3	−4.28 (17)
C6—C1—C2—C3	0.70 (19)	C9—C8—C13—C12	0.28 (18)
C1—C2—C3—C4	0.6 (2)	C7—C8—C13—C12	179.57 (11)
C2—C3—C4—C5	−1.3 (2)	C13—N3—C14—N1	−49.22 (13)
C3—C4—C5—C6	0.7 (2)	C13—N3—C14—C15	−171.00 (10)
C7—N2—C6—C5	−179.60 (13)	C7—N1—C14—N3	37.49 (14)
C7—N2—C6—C1	1.18 (14)	C1—N1—C14—N3	−160.71 (11)
C4—C5—C6—N2	−178.49 (13)	C7—N1—C14—C15	157.67 (11)
C4—C5—C6—C1	0.6 (2)	C1—N1—C14—C15	−40.53 (16)
N1—C1—C6—N2	0.28 (14)	N3—C14—C15—C20	42.18 (15)
C2—C1—C6—N2	177.93 (11)	N1—C14—C15—C20	−76.13 (14)
N1—C1—C6—C5	−179.00 (11)	N3—C14—C15—C16	−138.89 (12)
C2—C1—C6—C5	−1.36 (19)	N1—C14—C15—C16	102.80 (13)
C6—N2—C7—N1	−2.29 (14)	C20—C15—C16—O1	179.23 (11)
C6—N2—C7—C8	176.73 (12)	C14—C15—C16—O1	0.28 (17)
C1—N1—C7—N2	2.53 (14)	C20—C15—C16—C17	1.05 (18)
C14—N1—C7—N2	167.97 (10)	C14—C15—C16—C17	−177.90 (11)
C1—N1—C7—C8	−176.58 (10)	O1—C16—C17—C18	−177.68 (11)
C14—N1—C7—C8	−11.14 (17)	C15—C16—C17—C18	0.42 (18)
N2—C7—C8—C9	−7.4 (2)	C21—O2—C18—C19	8.93 (17)
N1—C7—C8—C9	171.60 (11)	C21—O2—C18—C17	−171.12 (11)
N2—C7—C8—C13	173.36 (12)	C16—C17—C18—O2	178.11 (11)
N1—C7—C8—C13	−7.68 (17)	C16—C17—C18—C19	−1.94 (18)
C13—C8—C9—C10	1.00 (19)	O2—C18—C19—C20	−178.13 (11)
C7—C8—C9—C10	−178.26 (12)	C17—C18—C19—C20	1.92 (18)
C8—C9—C10—C11	−1.12 (19)	C16—C15—C20—C19	−1.06 (18)
C9—C10—C11—C12	0.0 (2)	C14—C15—C20—C19	177.89 (11)
C10—C11—C12—C13	1.3 (2)	C18—C19—C20—C15	−0.41 (18)
C14—N3—C13—C12	−148.52 (12)

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C15–C20 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···O2ⁱ	0.907 (19)	2.211 (19)	3.0519 (15)	153.8 (17)
O1—H1O1···N2ⁱⁱ	0.98 (2)	1.72 (2)	2.6816 (15)	168 (2)
C2—H2A···Cg4	0.95	2.85	3.6277 (16)	140

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₇N₃O₂
M_r	343.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.5408 (1), 15.6503 (2), 11.7609 (1)
β (°)	110.408 (1)
V (Å³)	1645.87 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.28 × 0.25 × 0.22

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.974, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	31713, 6610, 4637
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.783

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.139, 1.05
No. of reflections	6610
No. of parameters	244
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.30

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

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C15–C20 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···O2ⁱ	0.907 (19)	2.211 (19)	3.0519 (15)	153.8 (17)
O1—H1O1···N2ⁱⁱ	0.98 (2)	1.72 (2)	2.6816 (15)	168 (2)
C2—H2A···Cg4	0.95	2.85	3.6277 (16)	140

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

Footnotes

‡Thomson Reuters ResearcherID: A-5085-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia for the RU research grant No. 1001/PKIMIA/815067. NEE thanks Universiti Sains Malaysia for a post-doctoral fellowship and the International University of Africa (Sudan) for providing study leave. The authors also thank the Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160.

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Volume 67| Part 9| September 2011| Pages o2410-o2411

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