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

Eltayeb, N.E.; Teoh, S.G.; Lo, K.M.

doi:10.1107/S1600536811034714

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2519

doi:10.1107/S1600536811034714

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

Naser Eltaher Eltayeb,^a,^b Siang Guan Teoh ^a ^* and Kong Mun Lo ^c

^aSchool of Chemical Sciences, Universiti Sains Malaysia, Minden, Penang, Malaysia, ^bDepartment of Chemistry, International University of Africa, Sudan, and ^cChemistry Department, Faculty of Science, University of Malaya, Malaysia
^*Correspondence e-mail: sgteoh@usm.my

(Received 16 August 2011; accepted 24 August 2011; online 31 August 2011)

In the title compound, C₂₂H₁₉N₃O₂, the phenol ring forms dihedral angles of 88.93 (10) and 87.95 (12)° with the benzimidazole system and the quinazoline benzene ring, respectively. In the crystal, molecules are linked via O—H⋯N hydrogen bonds into infinite chains along [100]. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring.

Related literature

For a related structure, references to our previous structural studies of similar compounds and background references to benzimidazoles, see: Eltayeb et al. (2011 ).

Experimental

Crystal data

C₂₂H₁₉N₃O₂
M_r = 357.40
Triclinic, $[P \overline 1]$
a = 8.6935 (3) Å
b = 10.9167 (3) Å
c = 11.3401 (5) Å
α = 107.193 (2)°
β = 108.923 (2)°
γ = 104.723 (2)°
V = 896.66 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.25 × 0.2 × 0.17 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.614, T_max = 0.746
7367 measured reflections
3505 independent reflections
2804 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.164
S = 1.00
3505 reflections
250 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯N1ⁱ	0.82	1.85	2.646 (3)	165
N2—H1N2⋯O1	1.01 (4)	2.12 (3)	2.811 (3)	124 (2)
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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 I, global. DOI: 10.1107/S1600536811034714/hb6367sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811034714/hb6367Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811034714/hb6367Isup3.cml

checkCIF report

Comment top

As part of our ongoing structural studies of benzimidazoles and their derivatives (Eltayeb et al., 2011, and references therein) we now describe in this paper the structure of the title compound, (I), (Fig. 1).

In the title compound, C₂₂H₁₉N₃O₂, the phenol-substituted ring forms dihedral angles of 88.93 (10) and 87.95 (12)° with the benzimidazole system and the quinazoline benzene ring, respectively. The phenol-substituted ring is perpendicular to the 10-membered quinazoline ring with dihedral angle 89.49 (9) °. The dihedral angle between the 9-membered benzimidazole and 10-membered quinazoline rings is 9.72 (8) °. The exthoxy group is planarly attached to the phenol ring.

In the crystal, molecules are linked via intermolecular O—H···N hydrogen bonds into infinite one-dimensional chain along [100]. The intramolecular N—H···O hydrogen bond generates an S(6) ring (Table 1).

C—H···π interactions are also present; C11—H11··· Cg5ⁱ =2.63 Å, C20—H20···Cg1ⁱⁱ = 2.79 Å and C21—H21A···Cg5ⁱⁱⁱ = 2.88 Å. Cg5 and Cg1 are centroids of C15—C20 and N1/C6/C1/N3/C7 rings respectively, [symmetry codes: (i) = 1-X,-Y,-Z; (ii) = X,Y,Z; (iii) =1-X,1-Y,1-Z].

Related literature top

For a related structure, references to our previous structural studies of similar compounds and background references to benzimidazoles, see: Eltayeb et al. (2011).

Experimental top

The title compound was synthesized by adding 3-ethoxthysalicylaldehyde (0.166 g, 1.0 mmol) to a solution of 2-(2-aminophenyl)-1H-benzimidazole 0.209 g, 1.0 mmol) in ethanol (30 ml). The color of the resulting solution is pale-yellow. Then upon adding zinc chloride (0.136 g, 1.0 mmol), the color of the solution became golden-yellow. The mixture was refluxed with stirring for 3 hrs. The resultant solution was filtered and the filtrate was evaporated to give a yellow solid product. Yellow blocks of (I) were obtained from ethanol by slow evaporation at room temperature after three weeks.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 (I) with 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound viewed down the b axis. Hydrogen bonds are shown as dashed lines.

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

Crystal data top

C₂₂H₁₉N₃O₂	Z = 2
M_r = 357.40	F(000) = 376
Triclinic, P1	D_x = 1.324 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6935 (3) Å	Cell parameters from 2997 reflections
b = 10.9167 (3) Å	θ = 2.6–28.3°
c = 11.3401 (5) Å	µ = 0.09 mm⁻¹
α = 107.193 (2)°	T = 296 K
β = 108.923 (2)°	Block, yellow
γ = 104.723 (2)°	0.25 × 0.2 × 0.17 mm
V = 896.66 (6) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3505 independent reflections
Radiation source: fine-focus sealed tube	2804 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
T_min = 0.614, T_max = 0.746	k = −13→13
7367 measured reflections	l = −13→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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0842P)² + 1.0545P] where P = (F_o² + 2F_c²)/3
3505 reflections	(Δ/σ)_max < 0.001
250 parameters	Δρ_max = 0.73 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₂₂H₁₉N₃O₂	γ = 104.723 (2)°
M_r = 357.40	V = 896.66 (6) Å³
Triclinic, P1	Z = 2
a = 8.6935 (3) Å	Mo Kα radiation
b = 10.9167 (3) Å	µ = 0.09 mm⁻¹
c = 11.3401 (5) Å	T = 296 K
α = 107.193 (2)°	0.25 × 0.2 × 0.17 mm
β = 108.923 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3505 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2804 reflections with I > 2σ(I)
T_min = 0.614, T_max = 0.746	R_int = 0.022
7367 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.73 e Å⁻³
3505 reflections	Δρ_min = −0.39 e Å⁻³
250 parameters

Special details top

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
O2	0.2462 (2)	0.30314 (16)	0.30490 (16)	0.0186 (4)
O1	0.3194 (2)	0.36858 (17)	0.10937 (16)	0.0198 (4)
H1O1	0.2499	0.3974	0.1312	0.030*
N2	0.5360 (3)	0.3168 (2)	−0.0210 (2)	0.0212 (4)
N3	0.8203 (3)	0.4820 (2)	0.1277 (2)	0.0199 (4)
C22	0.0082 (3)	0.1800 (3)	0.3379 (3)	0.0300 (6)
H22A	−0.0427	0.2463	0.3258	0.045*
H22B	−0.0237	0.1461	0.3992	0.045*
H22C	−0.0350	0.1037	0.2510	0.045*
C21	0.2056 (3)	0.2487 (2)	0.3970 (2)	0.0207 (5)
H21A	0.2514	0.3232	0.4869	0.025*
H21B	0.2584	0.1816	0.4059	0.025*
C17	0.4186 (3)	0.3471 (2)	0.3259 (2)	0.0159 (5)
C16	0.4501 (3)	0.3791 (2)	0.2227 (2)	0.0156 (5)
C15	0.6199 (3)	0.4154 (2)	0.2305 (2)	0.0158 (5)
C14	0.6409 (3)	0.4416 (2)	0.1107 (2)	0.0177 (5)
H14	0.6012	0.5163	0.1025	0.021*
C13	0.6001 (3)	0.2101 (2)	−0.0438 (2)	0.0196 (5)
C8	0.7844 (3)	0.2458 (2)	0.0104 (2)	0.0210 (5)
C9	0.8501 (3)	0.1412 (3)	−0.0197 (3)	0.0235 (5)
H9	0.9712	0.1637	0.0156	0.028*
C10	0.7343 (3)	0.0051 (2)	−0.1018 (3)	0.0264 (6)
H10	0.7770	−0.0647	−0.1212	0.032*
C18	0.5574 (3)	0.3556 (2)	0.4365 (2)	0.0181 (5)
H18	0.5371	0.3364	0.5060	0.022*
C19	0.7260 (3)	0.3924 (2)	0.4435 (2)	0.0193 (5)
H19	0.8183	0.3978	0.5177	0.023*
C20	0.7578 (3)	0.4213 (2)	0.3406 (2)	0.0184 (5)
H20	0.8707	0.4444	0.3449	0.022*
C11	0.5555 (3)	−0.0273 (3)	−0.1549 (3)	0.0276 (6)
H11	0.4786	−0.1194	−0.2106	0.033*
C12	0.4880 (3)	0.0721 (2)	−0.1280 (2)	0.0243 (5)
H12	0.3665	0.0474	−0.1661	0.029*
C7	0.8974 (3)	0.3931 (2)	0.0916 (2)	0.0193 (5)
N1	1.0679 (3)	0.4543 (2)	0.1332 (2)	0.0214 (4)
C6	1.1063 (3)	0.5952 (2)	0.2058 (2)	0.0202 (5)
C5	1.2674 (3)	0.7073 (3)	0.2714 (2)	0.0228 (5)
H5	1.3691	0.6958	0.2695	0.027*
C4	1.2708 (3)	0.8375 (3)	0.3399 (3)	0.0312 (6)
H4	1.3767	0.9147	0.3855	0.037*
C3	1.1143 (4)	0.8535 (3)	0.3410 (3)	0.0303 (6)
H3	1.1197	0.9411	0.3890	0.036*
C2	0.9543 (3)	0.7420 (3)	0.2726 (3)	0.0257 (5)
H2	0.8510	0.7523	0.2717	0.031*
C1	0.9549 (3)	0.6149 (2)	0.2056 (2)	0.0222 (5)
H1N2	0.409 (4)	0.280 (3)	−0.035 (3)	0.043 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0157 (8)	0.0213 (8)	0.0235 (8)	0.0083 (6)	0.0111 (7)	0.0116 (7)
O1	0.0160 (8)	0.0301 (9)	0.0206 (8)	0.0148 (7)	0.0098 (7)	0.0129 (7)
N2	0.0169 (10)	0.0223 (10)	0.0212 (10)	0.0076 (8)	0.0073 (8)	0.0062 (8)
N3	0.0174 (10)	0.0228 (10)	0.0222 (10)	0.0087 (8)	0.0097 (8)	0.0110 (8)
C22	0.0255 (13)	0.0367 (15)	0.0420 (15)	0.0142 (11)	0.0213 (12)	0.0250 (12)
C21	0.0246 (12)	0.0199 (11)	0.0237 (12)	0.0095 (9)	0.0141 (10)	0.0117 (9)
C17	0.0167 (11)	0.0114 (10)	0.0186 (11)	0.0066 (8)	0.0074 (9)	0.0040 (8)
C16	0.0178 (11)	0.0137 (10)	0.0162 (11)	0.0091 (8)	0.0067 (9)	0.0056 (8)
C15	0.0173 (11)	0.0134 (10)	0.0181 (11)	0.0076 (8)	0.0079 (9)	0.0065 (8)
C14	0.0164 (11)	0.0216 (11)	0.0226 (11)	0.0121 (9)	0.0107 (9)	0.0122 (9)
C13	0.0242 (12)	0.0247 (12)	0.0168 (11)	0.0144 (10)	0.0113 (10)	0.0106 (9)
C8	0.0279 (13)	0.0161 (11)	0.0140 (10)	0.0047 (9)	0.0066 (10)	0.0061 (9)
C9	0.0192 (12)	0.0267 (12)	0.0294 (13)	0.0120 (10)	0.0109 (10)	0.0147 (10)
C10	0.0370 (15)	0.0177 (12)	0.0274 (13)	0.0126 (10)	0.0168 (11)	0.0081 (10)
C18	0.0211 (11)	0.0158 (10)	0.0169 (11)	0.0057 (9)	0.0081 (9)	0.0072 (9)
C19	0.0161 (11)	0.0187 (11)	0.0167 (11)	0.0052 (9)	0.0014 (9)	0.0066 (9)
C20	0.0134 (11)	0.0182 (11)	0.0211 (11)	0.0061 (9)	0.0059 (9)	0.0066 (9)
C11	0.0325 (14)	0.0195 (12)	0.0263 (13)	0.0055 (10)	0.0127 (11)	0.0073 (10)
C12	0.0203 (12)	0.0244 (12)	0.0220 (12)	0.0026 (10)	0.0094 (10)	0.0063 (10)
C7	0.0198 (11)	0.0271 (12)	0.0178 (11)	0.0139 (10)	0.0095 (9)	0.0125 (10)
N1	0.0182 (10)	0.0255 (10)	0.0226 (10)	0.0091 (8)	0.0087 (8)	0.0125 (8)
C6	0.0217 (12)	0.0210 (11)	0.0152 (11)	0.0044 (9)	0.0048 (9)	0.0107 (9)
C5	0.0185 (12)	0.0310 (13)	0.0195 (11)	0.0085 (10)	0.0064 (9)	0.0142 (10)
C4	0.0291 (14)	0.0238 (13)	0.0233 (12)	−0.0064 (10)	0.0030 (11)	0.0107 (10)
C3	0.0426 (16)	0.0178 (12)	0.0272 (13)	0.0100 (11)	0.0131 (12)	0.0085 (10)
C2	0.0251 (13)	0.0269 (13)	0.0275 (13)	0.0097 (10)	0.0119 (11)	0.0138 (11)
C1	0.0215 (12)	0.0228 (12)	0.0202 (11)	0.0040 (9)	0.0068 (10)	0.0126 (10)

Geometric parameters (Å, º) top

O2—C17	1.367 (3)	C8—C7	1.461 (3)
O2—C21	1.438 (3)	C9—C10	1.379 (3)
O1—C16	1.362 (3)	C9—H9	0.9300
O1—H1O1	0.8200	C10—C11	1.375 (4)
N2—C13	1.407 (3)	C10—H10	0.9300
N2—C14	1.483 (3)	C18—C19	1.386 (3)
N2—H1N2	1.02 (3)	C18—H18	0.9300
N3—C7	1.354 (3)	C19—C20	1.386 (3)
N3—C1	1.401 (3)	C19—H19	0.9300
N3—C14	1.439 (3)	C20—H20	0.9300
C22—C21	1.503 (3)	C11—C12	1.364 (4)
C22—H22A	0.9600	C11—H11	0.9300
C22—H22B	0.9600	C12—H12	0.9300
C22—H22C	0.9600	C7—N1	1.312 (3)
C21—H21A	0.9700	N1—C6	1.403 (3)
C21—H21B	0.9700	C6—C1	1.385 (3)
C17—C18	1.389 (3)	C6—C5	1.389 (3)
C17—C16	1.402 (3)	C5—C4	1.391 (4)
C16—C15	1.394 (3)	C5—H5	0.9300
C15—C20	1.394 (3)	C4—C3	1.419 (4)
C15—C14	1.524 (3)	C4—H4	0.9300
C14—H14	0.9800	C3—C2	1.378 (4)
C13—C12	1.390 (3)	C3—H3	0.9300
C13—C8	1.414 (3)	C2—C1	1.373 (4)
C8—C9	1.404 (3)	C2—H2	0.9300

C17—O2—C21	116.69 (17)	C10—C9—H9	120.2
C16—O1—H1O1	109.5	C8—C9—H9	120.2
C13—N2—C14	117.46 (18)	C11—C10—C9	119.9 (2)
C13—N2—H1N2	111.6 (18)	C11—C10—H10	120.0
C14—N2—H1N2	109.0 (18)	C9—C10—H10	120.0
C7—N3—C1	106.87 (19)	C19—C18—C17	120.2 (2)
C7—N3—C14	125.18 (19)	C19—C18—H18	119.9
C1—N3—C14	126.96 (19)	C17—C18—H18	119.9
C21—C22—H22A	109.5	C20—C19—C18	120.4 (2)
C21—C22—H22B	109.5	C20—C19—H19	119.8
H22A—C22—H22B	109.5	C18—C19—H19	119.8
C21—C22—H22C	109.5	C19—C20—C15	119.7 (2)
H22A—C22—H22C	109.5	C19—C20—H20	120.1
H22B—C22—H22C	109.5	C15—C20—H20	120.1
O2—C21—C22	107.31 (19)	C12—C11—C10	121.7 (2)
O2—C21—H21A	110.3	C12—C11—H11	119.2
C22—C21—H21A	110.3	C10—C11—H11	119.2
O2—C21—H21B	110.3	C11—C12—C13	120.2 (2)
C22—C21—H21B	110.3	C11—C12—H12	119.9
H21A—C21—H21B	108.5	C13—C12—H12	119.9
O2—C17—C18	124.7 (2)	N1—C7—N3	113.7 (2)
O2—C17—C16	115.40 (19)	N1—C7—C8	128.5 (2)
C18—C17—C16	119.8 (2)	N3—C7—C8	117.8 (2)
O1—C16—C15	117.52 (19)	C7—N1—C6	104.17 (19)
O1—C16—C17	122.89 (19)	C1—C6—C5	120.5 (2)
C15—C16—C17	119.5 (2)	C1—C6—N1	110.7 (2)
C20—C15—C16	120.3 (2)	C5—C6—N1	128.8 (2)
C20—C15—C14	123.6 (2)	C6—C5—C4	117.4 (2)
C16—C15—C14	116.07 (19)	C6—C5—H5	121.3
N3—C14—N2	105.89 (17)	C4—C5—H5	121.3
N3—C14—C15	112.84 (18)	C5—C4—C3	120.6 (2)
N2—C14—C15	112.62 (18)	C5—C4—H4	119.7
N3—C14—H14	108.4	C3—C4—H4	119.7
N2—C14—H14	108.4	C2—C3—C4	121.4 (2)
C15—C14—H14	108.4	C2—C3—H3	119.3
C12—C13—N2	121.8 (2)	C4—C3—H3	119.3
C12—C13—C8	118.9 (2)	C1—C2—C3	116.7 (2)
N2—C13—C8	119.0 (2)	C1—C2—H2	121.7
C9—C8—C13	119.6 (2)	C3—C2—H2	121.7
C9—C8—C7	123.3 (2)	C2—C1—C6	123.3 (2)
C13—C8—C7	117.1 (2)	C2—C1—N3	132.2 (2)
C10—C9—C8	119.7 (2)	C6—C1—N3	104.5 (2)

C17—O2—C21—C22	−168.25 (19)	C16—C15—C20—C19	−0.8 (3)
C21—O2—C17—C18	−6.7 (3)	C14—C15—C20—C19	−178.3 (2)
C21—O2—C17—C16	170.40 (18)	C9—C10—C11—C12	−0.4 (4)
O2—C17—C16—O1	0.5 (3)	C10—C11—C12—C13	−0.7 (4)
C18—C17—C16—O1	177.77 (19)	N2—C13—C12—C11	175.7 (2)
O2—C17—C16—C15	−175.55 (18)	C8—C13—C12—C11	1.5 (4)
C18—C17—C16—C15	1.7 (3)	C1—N3—C7—N1	−2.4 (3)
O1—C16—C15—C20	−176.86 (19)	C14—N3—C7—N1	−171.7 (2)
C17—C16—C15—C20	−0.6 (3)	C1—N3—C7—C8	179.14 (19)
O1—C16—C15—C14	0.8 (3)	C14—N3—C7—C8	9.9 (3)
C17—C16—C15—C14	177.08 (18)	C9—C8—C7—N1	9.6 (4)
C7—N3—C14—N2	−37.3 (3)	C13—C8—C7—N1	−167.8 (2)
C1—N3—C14—N2	155.6 (2)	C9—C8—C7—N3	−172.1 (2)
C7—N3—C14—C15	86.4 (3)	C13—C8—C7—N3	10.4 (3)
C1—N3—C14—C15	−80.8 (3)	N3—C7—N1—C6	1.5 (3)
C13—N2—C14—N3	48.0 (3)	C8—C7—N1—C6	179.8 (2)
C13—N2—C14—C15	−75.8 (2)	C7—N1—C6—C1	0.0 (3)
C20—C15—C14—N3	−3.9 (3)	C7—N1—C6—C5	−179.5 (2)
C16—C15—C14—N3	178.50 (18)	C1—C6—C5—C4	2.3 (3)
C20—C15—C14—N2	115.9 (2)	N1—C6—C5—C4	−178.3 (2)
C16—C15—C14—N2	−61.7 (2)	C6—C5—C4—C3	−0.5 (4)
C14—N2—C13—C12	152.2 (2)	C5—C4—C3—C2	−1.2 (4)
C14—N2—C13—C8	−33.6 (3)	C4—C3—C2—C1	1.1 (4)
C12—C13—C8—C9	−1.2 (3)	C3—C2—C1—C6	0.8 (4)
N2—C13—C8—C9	−175.5 (2)	C3—C2—C1—N3	179.8 (2)
C12—C13—C8—C7	176.4 (2)	C5—C6—C1—C2	−2.5 (4)
N2—C13—C8—C7	2.0 (3)	N1—C6—C1—C2	177.9 (2)
C13—C8—C9—C10	0.1 (4)	C5—C6—C1—N3	178.2 (2)
C7—C8—C9—C10	−177.3 (2)	N1—C6—C1—N3	−1.4 (2)
C8—C9—C10—C11	0.7 (4)	C7—N3—C1—C2	−177.0 (3)
O2—C17—C18—C19	175.5 (2)	C14—N3—C1—C2	−8.0 (4)
C16—C17—C18—C19	−1.5 (3)	C7—N3—C1—C6	2.2 (2)
C17—C18—C19—C20	0.1 (3)	C14—N3—C1—C6	171.2 (2)
C18—C19—C20—C15	1.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1ⁱ	0.82	1.85	2.646 (3)	165
N2—H1N2···O1	1.01 (4)	2.12 (3)	2.811 (3)	124 (2)

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₉N₃O₂
M_r	357.40
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.6935 (3), 10.9167 (3), 11.3401 (5)
α, β, γ (°)	107.193 (2), 108.923 (2), 104.723 (2)
V (Å³)	896.66 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.2 × 0.17

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.614, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	7367, 3505, 2804
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.164, 1.00
No. of reflections	3505
No. of parameters	250
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.39

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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
O1—H1O1···N1ⁱ	0.82	1.85	2.646 (3)	165
N2—H1N2···O1	1.01 (4)	2.12 (3)	2.811 (3)	124 (2)

Symmetry code: (i) x−1, y, z.

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia for the RU research grant (1001/PKIMIA/815067). NEE thanks Universiti Sains Malaysia for a post-doctoral fellowship and the International University of Africa (Sudan) for providing research leave.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Eltayeb, N. E., Teoh, S. G., Quah, C. K. & Fun, H.-K. (2011). Acta Cryst. E67, o2243–o2244. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar