N-Butyl-4,6-diphenyl­pyrimidin-2-amine

Fun, H.-K.; Hemamalini, M.; Hazra, A.; Goswami, S.

doi:10.1107/S160053681104147X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2956

doi:10.1107/S160053681104147X

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N-Butyl-4,6-diphenylpyrimidin-2-amine

Hoong-Kun Fun,^a ^*‡ Madhukar Hemamalini,^a Anita Hazra ^b and Shyamaprosad Goswami ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Bengal Engineering and Science University, Shibpur, Howrah 711 103, India
^*Correspondence e-mail: hkfun@usm.my

(Received 5 October 2011; accepted 8 October 2011; online 12 October 2011)

In the title compound, C₂₀H₂₁N₃, the pyrimidine ring is inclined at dihedral angles of 51.57 (4) and 2.49 (4)° to the two phenyl rings. The dihedral angle between the two terminal phenyl rings is 50.44 (4)°. In the crystal, adjacent molecules are linked via a pair of N—H⋯N hydrogen bonds, forming an inversion dimer with an R₂²(8) ring motif. Furthermore, the crystal structure is stabilized by a weak π–π interaction, with a centroid–centroid distance of 3.6065 (5) Å.

Related literature

For biological applications of pyrimidine derivatives, see: Katrizky et al. (1982 ); Brown & Lyall (1964 ). For the synthesis, see: Goswami et al. (2009 ). For graph-set notation, see: Bernstein et al. (1995 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₀H₂₁N₃
M_r = 303.40
Triclinic, $[P \overline 1]$
a = 8.1544 (1) Å
b = 9.5284 (1) Å
c = 11.3237 (2) Å
α = 77.090 (1)°
β = 74.152 (1)°
γ = 71.288 (1)°
V = 792.70 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.47 × 0.25 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.965, T_max = 0.993
26407 measured reflections
6933 independent reflections
5769 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.136
S = 1.04
6933 reflections
292 parameters
All H-atom parameters refined
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N3⋯N1ⁱ	0.869 (15)	2.262 (15)	3.1249 (10)	172.4 (15)
Symmetry code: (i) -x+1, -y+2, -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 global, I. DOI: 10.1107/S160053681104147X/is2788sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681104147X/is2788Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681104147X/is2788Isup3.cml

checkCIF report

Comment top

Substituted pyrimidine derivatives are utilized as antiviral and antifungal agents (Katrizky et al., 1982; Brown & Lyall, 1964). 2-Butylamino-4,6-diphenyl pyrimidine has been synthesized by solid-phase microwave irradiation (Goswami et al., 2009). The crystal structure of 2-butylamino-4,6-diphenylpyrimidine is reported here.

The molecular structure of the title compound is shown in Fig. 1. The pyrimidine (N1/N2/C7–C9/C16) ring is inclined at dihedral angles of 51.57 (4) and 2.49 (4)°, respectively, to the two phenyl (C1–C6 and C10–C15) rings. The corresponding angle between the two terminal phenyl (C1–C6 and C10–C15) rings is 50.44 (4)°.

In the crystal, (Fig. 2), the adjacent molecules are linked via a pair of N—H···N (Table 1) hydrogen bonds, forming an inversion dimer with an R₂²(8) ring motif (Bernstein et al., 1995). The crystal structure is further stabilized by a weak π–π interaction between the pyrimidine (Cg1; N1/N2/C7–C9/C16) and phenyl (Cg3; C10–C15) rings [Cg1···Cg3ⁱⁱ = 3.6065 (5) Å; (ii) 1 - x, 1 - y, -z].

Related literature top

For biological applications of pyrimidine derivatives, see: Katrizky et al. (1982); Brown & Lyall (1964). For the synthesis, see: Goswami et al. (2009). For graph-set notation, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of S-methylisothiourea sulphate (556 mg, 2 mmol), potassium carbonate (345 mg, 2.5 mmol) and butylamine (292 mg, 4 mmol) was irradiated at 450 Watt for 12 minutes in a microwave oven. The solid mass was washed with chloroform to remove the unreacted butylamine and then dried. The solid residue was then mixed with dibenzoylmethane (896 mg, 4 mmol) and again irradiated at 300 Watt for 6 minutes. Water was added to it and the contents were extracted with chloroform. The crude product was then purified through column chromatography (silica gel, 100–200 mesh) using 10% ethyl acetate in petroleum ether as an eluent to afford pure compound. The single crystal was grown by slow evaporation of a chloroform and methanol (3:1) solution (m.p. 65–66 °C).

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 the title compound, showing 50% probability displacement ellipsoids.
	Fig. 2. A crystal packing view of the title compound along the b axis.

N-Butyl-4,6-diphenylpyrimidin-2-amine top

Crystal data top

C₂₀H₂₁N₃	Z = 2
M_r = 303.40	F(000) = 324
Triclinic, P1	D_x = 1.271 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1544 (1) Å	Cell parameters from 8544 reflections
b = 9.5284 (1) Å	θ = 2.7–35.6°
c = 11.3237 (2) Å	µ = 0.08 mm⁻¹
α = 77.090 (1)°	T = 100 K
β = 74.152 (1)°	Block, colourless
γ = 71.288 (1)°	0.47 × 0.25 × 0.09 mm
V = 792.70 (2) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6933 independent reflections
Radiation source: fine-focus sealed tube	5769 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ϕ and ω scans	θ_max = 35.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→12
T_min = 0.965, T_max = 0.993	k = −15→15
26407 measured reflections	l = −18→17

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	All H-atom parameters refined
S = 1.04	w = 1/[σ²(F_o²) + (0.0772P)² + 0.1237P] where P = (F_o² + 2F_c²)/3
6933 reflections	(Δ/σ)_max = 0.001
292 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₀H₂₁N₃	γ = 71.288 (1)°
M_r = 303.40	V = 792.70 (2) Å³
Triclinic, P1	Z = 2
a = 8.1544 (1) Å	Mo Kα radiation
b = 9.5284 (1) Å	µ = 0.08 mm⁻¹
c = 11.3237 (2) Å	T = 100 K
α = 77.090 (1)°	0.47 × 0.25 × 0.09 mm
β = 74.152 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6933 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5769 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.993	R_int = 0.031
26407 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.136	All H-atom parameters refined
S = 1.04	Δρ_max = 0.56 e Å⁻³
6933 reflections	Δρ_min = −0.31 e Å⁻³
292 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 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
N1	0.36098 (9)	0.87806 (7)	−0.01978 (6)	0.01301 (12)
N2	0.37435 (8)	0.65917 (7)	0.13733 (6)	0.01297 (12)
N3	0.48902 (9)	0.84810 (7)	0.14526 (6)	0.01494 (12)
C1	0.25894 (11)	0.85602 (8)	−0.30090 (7)	0.01612 (14)
C2	0.19425 (11)	0.94496 (9)	−0.40295 (8)	0.01783 (15)
C3	0.08601 (11)	1.09047 (9)	−0.39389 (8)	0.01712 (14)
C4	0.04519 (10)	1.14759 (8)	−0.28338 (8)	0.01701 (14)
C5	0.11410 (10)	1.06024 (8)	−0.18232 (7)	0.01555 (14)
C6	0.22075 (10)	0.91331 (8)	−0.19031 (7)	0.01279 (13)
C7	0.28463 (10)	0.81869 (8)	−0.07941 (7)	0.01245 (12)
C8	0.25519 (10)	0.67743 (8)	−0.03777 (7)	0.01350 (13)
C9	0.30031 (9)	0.60099 (7)	0.07420 (7)	0.01186 (12)
C10	0.26882 (9)	0.45275 (7)	0.13143 (7)	0.01231 (12)
C11	0.31422 (10)	0.38330 (8)	0.24527 (7)	0.01509 (13)
C12	0.28902 (11)	0.24334 (8)	0.29942 (8)	0.01732 (14)
C13	0.21705 (11)	0.17083 (8)	0.24098 (8)	0.01694 (14)
C14	0.17268 (11)	0.23799 (8)	0.12759 (8)	0.01749 (14)
C15	0.19841 (10)	0.37773 (8)	0.07272 (8)	0.01567 (14)
C16	0.40608 (10)	0.79250 (7)	0.08610 (7)	0.01233 (12)
C17	0.51118 (10)	0.78847 (8)	0.27152 (7)	0.01481 (13)
C18	0.66070 (11)	0.64437 (8)	0.28644 (7)	0.01577 (14)
C19	0.68324 (11)	0.60211 (8)	0.42038 (8)	0.01700 (14)
C20	0.82332 (13)	0.45432 (10)	0.44264 (10)	0.02491 (18)
H1	0.3360 (16)	0.7506 (14)	−0.3075 (11)	0.021 (3)*
H2	0.2272 (18)	0.9035 (15)	−0.4830 (12)	0.027 (3)*
H3	0.0400 (17)	1.1531 (14)	−0.4640 (12)	0.022 (3)*
H4	−0.0327 (17)	1.2473 (14)	−0.2754 (12)	0.024 (3)*
H5	0.0862 (16)	1.1020 (13)	−0.1050 (11)	0.021 (3)*
H8	0.2022 (17)	0.6372 (14)	−0.0856 (12)	0.025 (3)*
H11	0.3622 (17)	0.4368 (14)	0.2855 (12)	0.025 (3)*
H12	0.3224 (18)	0.1965 (14)	0.3804 (13)	0.027 (3)*
H13	0.1961 (18)	0.0735 (15)	0.2800 (13)	0.029 (3)*
H14	0.1241 (18)	0.1847 (15)	0.0865 (12)	0.028 (3)*
H15	0.1669 (18)	0.4180 (14)	−0.0092 (12)	0.026 (3)*
H17A	0.3985 (16)	0.7737 (13)	0.3224 (11)	0.017 (3)*
H17B	0.5357 (16)	0.8685 (13)	0.3029 (11)	0.018 (3)*
H18A	0.7692 (17)	0.6580 (14)	0.2288 (12)	0.023 (3)*
H18B	0.6321 (17)	0.5604 (14)	0.2616 (12)	0.026 (3)*
H19A	0.7185 (17)	0.6833 (14)	0.4430 (12)	0.023 (3)*
H19B	0.5682 (17)	0.5940 (13)	0.4765 (12)	0.022 (3)*
H20A	0.938 (2)	0.4555 (16)	0.3902 (14)	0.036 (4)*
H20B	0.8407 (19)	0.4286 (16)	0.5301 (14)	0.034 (4)*
H20C	0.7926 (19)	0.3696 (16)	0.4220 (13)	0.033 (3)*
H1N3	0.5202 (19)	0.9295 (16)	0.1112 (13)	0.031 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0155 (3)	0.0116 (2)	0.0130 (3)	−0.00496 (19)	−0.0050 (2)	−0.00004 (19)
N2	0.0150 (3)	0.0112 (2)	0.0137 (3)	−0.00512 (19)	−0.0040 (2)	−0.00066 (19)
N3	0.0221 (3)	0.0124 (2)	0.0142 (3)	−0.0083 (2)	−0.0081 (2)	0.0009 (2)
C1	0.0197 (3)	0.0139 (3)	0.0158 (3)	−0.0044 (2)	−0.0064 (3)	−0.0018 (2)
C2	0.0220 (4)	0.0188 (3)	0.0143 (3)	−0.0066 (3)	−0.0067 (3)	−0.0010 (2)
C3	0.0175 (3)	0.0179 (3)	0.0167 (3)	−0.0071 (2)	−0.0070 (3)	0.0031 (2)
C4	0.0165 (3)	0.0142 (3)	0.0185 (4)	−0.0033 (2)	−0.0051 (3)	0.0013 (2)
C5	0.0167 (3)	0.0137 (3)	0.0150 (3)	−0.0033 (2)	−0.0035 (3)	−0.0008 (2)
C6	0.0142 (3)	0.0119 (3)	0.0131 (3)	−0.0053 (2)	−0.0042 (2)	0.0006 (2)
C7	0.0134 (3)	0.0118 (3)	0.0122 (3)	−0.0038 (2)	−0.0031 (2)	−0.0012 (2)
C8	0.0165 (3)	0.0120 (3)	0.0137 (3)	−0.0057 (2)	−0.0052 (2)	−0.0005 (2)
C9	0.0122 (3)	0.0108 (3)	0.0128 (3)	−0.0038 (2)	−0.0023 (2)	−0.0017 (2)
C10	0.0123 (3)	0.0109 (3)	0.0139 (3)	−0.0043 (2)	−0.0023 (2)	−0.0010 (2)
C11	0.0184 (3)	0.0142 (3)	0.0137 (3)	−0.0070 (2)	−0.0041 (3)	0.0002 (2)
C12	0.0210 (3)	0.0152 (3)	0.0152 (3)	−0.0077 (2)	−0.0032 (3)	0.0019 (2)
C13	0.0174 (3)	0.0122 (3)	0.0203 (4)	−0.0063 (2)	−0.0011 (3)	−0.0009 (2)
C14	0.0189 (3)	0.0144 (3)	0.0220 (4)	−0.0077 (2)	−0.0052 (3)	−0.0026 (3)
C15	0.0182 (3)	0.0134 (3)	0.0175 (3)	−0.0063 (2)	−0.0062 (3)	−0.0008 (2)
C16	0.0139 (3)	0.0109 (3)	0.0128 (3)	−0.0040 (2)	−0.0035 (2)	−0.0014 (2)
C17	0.0191 (3)	0.0131 (3)	0.0139 (3)	−0.0045 (2)	−0.0067 (3)	−0.0016 (2)
C18	0.0187 (3)	0.0137 (3)	0.0166 (3)	−0.0041 (2)	−0.0069 (3)	−0.0024 (2)
C19	0.0203 (3)	0.0147 (3)	0.0177 (4)	−0.0052 (2)	−0.0082 (3)	−0.0002 (2)
C20	0.0288 (4)	0.0190 (4)	0.0285 (5)	−0.0016 (3)	−0.0166 (4)	−0.0012 (3)

Geometric parameters (Å, º) top

N1—C7	1.3378 (9)	C10—C11	1.3996 (10)
N1—C16	1.3598 (9)	C10—C15	1.4024 (10)
N2—C9	1.3455 (9)	C11—C12	1.3923 (10)
N2—C16	1.3479 (9)	C11—H11	0.974 (13)
N3—C16	1.3502 (9)	C12—C13	1.3914 (11)
N3—C17	1.4532 (10)	C12—H12	0.995 (13)
N3—H1N3	0.869 (14)	C13—C14	1.3883 (11)
C1—C2	1.3930 (11)	C13—H13	0.980 (14)
C1—C6	1.3952 (11)	C14—C15	1.3933 (11)
C1—H1	1.006 (12)	C14—H14	0.983 (14)
C2—C3	1.3931 (11)	C15—H15	0.991 (13)
C2—H2	1.005 (13)	C17—C18	1.5281 (10)
C3—C4	1.3905 (12)	C17—H17A	0.976 (12)
C3—H3	0.967 (13)	C17—H17B	1.002 (12)
C4—C5	1.3942 (11)	C18—C19	1.5259 (11)
C4—H4	0.967 (13)	C18—H18A	0.973 (13)
C5—C6	1.3989 (10)	C18—H18B	1.015 (13)
C5—H5	0.983 (12)	C19—C20	1.5224 (11)
C6—C7	1.4870 (10)	C19—H19A	1.009 (13)
C7—C8	1.3977 (10)	C19—H19B	0.995 (13)
C8—C9	1.3942 (10)	C20—H20A	0.961 (15)
C8—H8	0.977 (13)	C20—H20B	1.003 (14)
C9—C10	1.4879 (10)	C20—H20C	1.007 (14)

C7—N1—C16	115.44 (6)	C13—C12—H12	120.7 (8)
C9—N2—C16	117.01 (6)	C11—C12—H12	119.1 (8)
C16—N3—C17	122.97 (6)	C14—C13—C12	119.61 (7)
C16—N3—H1N3	119.7 (9)	C14—C13—H13	120.0 (8)
C17—N3—H1N3	116.9 (9)	C12—C13—H13	120.4 (8)
C2—C1—C6	120.39 (7)	C13—C14—C15	120.42 (7)
C2—C1—H1	119.9 (7)	C13—C14—H14	118.8 (8)
C6—C1—H1	119.7 (7)	C15—C14—H14	120.8 (8)
C1—C2—C3	120.08 (7)	C14—C15—C10	120.50 (7)
C1—C2—H2	119.4 (7)	C14—C15—H15	116.3 (7)
C3—C2—H2	120.5 (7)	C10—C15—H15	123.2 (7)
C4—C3—C2	119.84 (7)	N2—C16—N3	117.51 (6)
C4—C3—H3	119.3 (7)	N2—C16—N1	126.16 (7)
C2—C3—H3	120.8 (7)	N3—C16—N1	116.33 (6)
C3—C4—C5	120.14 (7)	N3—C17—C18	115.74 (6)
C3—C4—H4	120.4 (8)	N3—C17—H17A	108.5 (7)
C5—C4—H4	119.4 (8)	C18—C17—H17A	110.1 (7)
C4—C5—C6	120.25 (7)	N3—C17—H17B	106.5 (7)
C4—C5—H5	119.7 (7)	C18—C17—H17B	108.5 (7)
C6—C5—H5	120.1 (7)	H17A—C17—H17B	107.3 (10)
C1—C6—C5	119.26 (7)	C19—C18—C17	110.79 (6)
C1—C6—C7	121.10 (6)	C19—C18—H18A	111.7 (7)
C5—C6—C7	119.58 (7)	C17—C18—H18A	108.8 (7)
N1—C7—C8	122.79 (7)	C19—C18—H18B	109.7 (7)
N1—C7—C6	117.19 (6)	C17—C18—H18B	109.1 (7)
C8—C7—C6	119.93 (6)	H18A—C18—H18B	106.6 (10)
C9—C8—C7	117.28 (6)	C20—C19—C18	113.18 (7)
C9—C8—H8	122.7 (8)	C20—C19—H19A	108.2 (7)
C7—C8—H8	120.0 (8)	C18—C19—H19A	109.3 (7)
N2—C9—C8	121.17 (6)	C20—C19—H19B	108.4 (7)
N2—C9—C10	116.16 (6)	C18—C19—H19B	109.2 (7)
C8—C9—C10	122.67 (6)	H19A—C19—H19B	108.4 (10)
C11—C10—C15	118.50 (6)	C19—C20—H20A	112.0 (9)
C11—C10—C9	119.78 (6)	C19—C20—H20B	112.9 (8)
C15—C10—C9	121.71 (7)	H20A—C20—H20B	106.1 (12)
C12—C11—C10	120.77 (7)	C19—C20—H20C	110.9 (8)
C12—C11—H11	121.4 (8)	H20A—C20—H20C	105.5 (12)
C10—C11—H11	117.8 (8)	H20B—C20—H20C	109.0 (11)
C13—C12—C11	120.19 (7)

C6—C1—C2—C3	−2.07 (12)	C8—C9—C10—C11	−178.80 (7)
C1—C2—C3—C4	1.10 (12)	N2—C9—C10—C15	−177.66 (6)
C2—C3—C4—C5	0.79 (12)	C8—C9—C10—C15	2.87 (11)
C3—C4—C5—C6	−1.73 (12)	C15—C10—C11—C12	−0.40 (11)
C2—C1—C6—C5	1.13 (12)	C9—C10—C11—C12	−178.79 (7)
C2—C1—C6—C7	178.34 (7)	C10—C11—C12—C13	−0.37 (12)
C4—C5—C6—C1	0.76 (11)	C11—C12—C13—C14	0.84 (12)
C4—C5—C6—C7	−176.49 (7)	C12—C13—C14—C15	−0.53 (12)
C16—N1—C7—C8	−1.02 (11)	C13—C14—C15—C10	−0.24 (12)
C16—N1—C7—C6	175.47 (6)	C11—C10—C15—C14	0.71 (11)
C1—C6—C7—N1	132.94 (8)	C9—C10—C15—C14	179.06 (7)
C5—C6—C7—N1	−49.86 (10)	C9—N2—C16—N3	−176.52 (6)
C1—C6—C7—C8	−50.47 (10)	C9—N2—C16—N1	4.11 (11)
C5—C6—C7—C8	126.73 (8)	C17—N3—C16—N2	−13.28 (11)
N1—C7—C8—C9	3.34 (11)	C17—N3—C16—N1	166.16 (7)
C6—C7—C8—C9	−173.05 (6)	C7—N1—C16—N2	−2.90 (11)
C16—N2—C9—C8	−1.39 (10)	C7—N1—C16—N3	177.72 (6)
C16—N2—C9—C10	179.13 (6)	C16—N3—C17—C18	78.93 (9)
C7—C8—C9—N2	−2.05 (11)	N3—C17—C18—C19	174.06 (6)
C7—C8—C9—C10	177.40 (6)	C17—C18—C19—C20	176.63 (7)
N2—C9—C10—C11	0.68 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···N1ⁱ	0.869 (15)	2.262 (15)	3.1249 (10)	172.4 (15)

Symmetry code: (i) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₁N₃
M_r	303.40
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.1544 (1), 9.5284 (1), 11.3237 (2)
α, β, γ (°)	77.090 (1), 74.152 (1), 71.288 (1)
V (Å³)	792.70 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.47 × 0.25 × 0.09

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.965, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	26407, 6933, 5769
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.807

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.136, 1.04
No. of reflections	6933
No. of parameters	292
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.31

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
N3—H1N3···N1ⁱ	0.869 (15)	2.262 (15)	3.1249 (10)	172.4 (15)

Symmetry code: (i) −x+1, −y+2, −z.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. MH also thanks Universiti Sains Malaysia for a post-doctoral research fellowship. SG and AH thank the CSIR [No. 01 (2292)/09/EMR-II], Government of India, for financial support.

References

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