Ethyl 1-sec-butyl-2-(4-fluoro­phen­yl)-1H-benzimidazole-5-carboxyl­ate

Arumugam, N.; Ngah, N.; Abd Hamid, S.; Abdul Rahim, A.S.

doi:10.1107/S1600536811041663

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2938

doi:10.1107/S1600536811041663

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Ethyl 1-sec-butyl-2-(4-fluorophenyl)-1H-benzimidazole-5-carboxylate

Natarajan Arumugam,^a Nurziana Ngah,^b Shafida Abd Hamid ^b and Aisyah Saad Abdul Rahim ^a ^*

^aSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bKulliyyah of Science, International Islamic University Malaysia, Kuantan Campus, Jalan Istana, Bandar Indera Mahkota, 25200 Kuantan, Pahang, Malaysia
^*Correspondence e-mail: aisyah@usm.my

(Received 4 October 2011; accepted 10 October 2011; online 12 October 2011)

In the title compound, C₂₀H₂₁FN₂O₂, the benzene ring and the benzimidazole ring system are inclined at a dihedral angle of 44.40 (9)°. In the crystal, molecules are linked by intermolecular C—H⋯O hydrogen bonds, forming a zigzag chain along the b-axis direction. An intramolecular C—H⋯π interaction is also observed.

Related literature

For the synthesis of the title compound and related structures, see: Arumugam, Abd Hamid et al. (2010 ); Arumugam, Abdul Rahim, Osman, Hemamalini & Fun (2010 ); Arumugam, Abdul Rahim, Osman, Quah & Fun (2010 ). For applications of benzimidazole derivatives, see: Spasov et al. (1999 ); Easmon et al. (2001 ); Özden et al. (2004 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₀H₂₁FN₂O₂
M_r = 340.39
Monoclinic, P 2₁ /c
a = 10.2249 (16) Å
b = 12.3767 (18) Å
c = 14.149 (2) Å
β = 93.473 (2)°
V = 1787.3 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.37 × 0.20 × 0.11 mm

Data collection

Bruker APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.968, T_max = 0.990
10465 measured reflections
3130 independent reflections
2342 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.150
S = 1.05
3130 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C7/N2/C1/C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1ⁱ	0.93	2.53	3.452 (3)	169
C20—H20C⋯O1ⁱ	0.96	2.59	3.485 (4)	154
C19—H19A⋯Cg1	0.96	2.82	3.400 (3)	121
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536811041663/is2787sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811041663/is2787Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811041663/is2787Isup3.cml

checkCIF report

Comment top

The synthesis of benzimidazole heterocycles is ever fascinating since they promise a wide spectrum of pharmacological activities such as antibacterial (Özden et al., 2004), anticancer (Easmon et al., 2001) and antifungal (Spasov et al., 1999). As the benzimidazole derivative is of much importance, we have undertaken the X-ray crystal structure determination of the title compound.

The title compound (Fig. 1) is similar to those previously reported ethyl-1-sec-butyl-2-(4-chlorophenyl)-1H-benzimidazole-5-carboxylate (Arumugam, Abdul Rahim, Osman, Quah & Fun, 2010) except the fluorine atom is attached at the para position of the phenyl ring. The phenyl (C8/C9/C10/ C11/C12/C13) and benzimidazole (N1/N2/C1/C2/C3/C4/C5) fragments are essentially planar with maximum deviation is 0.005 (2)Å for atom C2. Both fragments are inclined to each other by 44.40 (9)°. The bond lengths are in normal ranges (Allen et al., 1987) and in agreement to those reported by Arumugam et al. (Arumugam, Abd Hamid et al., 2010; Arumugam, Abdul Rahim, Osman, Hemamalini & Fun, 2010; Arumugam, Abdul Rahim, Osman, Quah & Fun, 2010). In the crystal structure (Fig. 2), the molecules are linked by intermolecular C5—H5···O1ⁱ and C20—H20C···O1ⁱ hydrogen bonds (symmetry codes as in Table 1) to form a zigzag chain along the b axis. The molecular structure is further stabilized by an intramolecular C—H···Cg1 (Table 1) interaction; Cg1 is the centroid of the N1/C7/N2/C1/C6 ring.

Related literature top

For the synthesis of the title compound and related structures, see: Arumugam, Abd Hamid et al. (2010); Arumugam, Abdul Rahim, Osman, Hemamalini & Fun (2010); Arumugam, Abdul Rahim, Osman, Quah & Fun (2010). For applications of benzimidazole derivatives, see: Spasov et al. (1999); Easmon et al. (2001); Özden et al. (2004). For bond-length data, see: Allen et al. (1987).

Experimental top

A solution of ethyl-3-amino-4-(sec-butylamino) benzoate (1.0 mmol) and sodium bisulfite adduct of 4-fluorobenzaldehyde (3.5 mmol) in DMF was treated under microwave conditions at 130 °C for 2 minutes. The reaction mixture was diluted in EtOAc (20 ml) and washed with H₂O (20 ml). The organic layer was collected and dried with Na₂SO₄. The solvent was evaporated in vacuo to afford a crude product. Recrystallization of the crude product gave the title compound as colourless crystal.

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, with the atom-numbering scheme and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. A molecular packing diagram of the title compound, viewed down the c axis.

Ethyl 1-sec-butyl-2-(4-fluorophenyl)-1H-benzimidazole- 5-carboxylate top

Crystal data top

C₂₀H₂₁FN₂O₂	F(000) = 720
M_r = 340.39	D_x = 1.265 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2853 reflections
a = 10.2249 (16) Å	θ = 2.0–25.0°
b = 12.3767 (18) Å	µ = 0.09 mm⁻¹
c = 14.149 (2) Å	T = 293 K
β = 93.473 (2)°	Block, colourless
V = 1787.3 (5) Å³	0.37 × 0.20 × 0.11 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD diffractometer	3130 independent reflections
Radiation source: fine-focus sealed tube	2342 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 83.66 pixels mm^-1	θ_max = 25.0°, θ_min = 2.0°
ϕ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −14→14
T_min = 0.968, T_max = 0.990	l = −16→16
10465 measured reflections

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) = 0.150	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0825P)² + 0.313P] where P = (F_o² + 2F_c²)/3
3130 reflections	(Δ/σ)_max = 0.001
229 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₀H₂₁FN₂O₂	V = 1787.3 (5) Å³
M_r = 340.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.2249 (16) Å	µ = 0.09 mm⁻¹
b = 12.3767 (18) Å	T = 293 K
c = 14.149 (2) Å	0.37 × 0.20 × 0.11 mm
β = 93.473 (2)°

Data collection top

Bruker APEXII DUO CCD diffractometer	3130 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2342 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.990	R_int = 0.027
10465 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.150	H-atom parameters constrained
S = 1.05	Δρ_max = 0.21 e Å⁻³
3130 reflections	Δρ_min = −0.20 e Å⁻³
229 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
F1	1.45030 (16)	1.11874 (14)	0.07109 (13)	0.1053 (6)
O1	0.49279 (17)	0.52863 (13)	0.17567 (13)	0.0764 (5)
O2	0.65827 (16)	0.47066 (12)	0.09413 (12)	0.0696 (5)
N1	0.89771 (15)	0.92002 (12)	0.18887 (11)	0.0456 (4)
N2	0.98670 (15)	0.78337 (12)	0.10912 (11)	0.0468 (4)
C1	0.86373 (18)	0.75303 (14)	0.13674 (12)	0.0421 (4)
C2	0.79676 (19)	0.65643 (15)	0.12078 (13)	0.0458 (5)
H2	0.8334	0.6006	0.0872	0.055*
C3	0.67392 (19)	0.64541 (15)	0.15618 (13)	0.0467 (5)
C4	0.6195 (2)	0.73015 (17)	0.20597 (15)	0.0537 (5)
H4	0.5372	0.7208	0.2293	0.064*
C5	0.68326 (19)	0.82662 (17)	0.22166 (15)	0.0542 (5)
H5	0.6456	0.8827	0.2543	0.065*
C6	0.80724 (18)	0.83677 (15)	0.18631 (13)	0.0439 (5)
C7	1.00272 (18)	0.88255 (15)	0.14109 (12)	0.0428 (4)
C8	1.11991 (18)	0.94762 (15)	0.12502 (13)	0.0443 (5)
C9	1.1114 (2)	1.05455 (17)	0.09460 (14)	0.0557 (5)
H9	1.0297	1.0875	0.0865	0.067*
C10	1.2223 (3)	1.11195 (19)	0.07637 (16)	0.0658 (6)
H10	1.2166	1.1834	0.0561	0.079*
C11	1.3408 (2)	1.0617 (2)	0.08865 (17)	0.0672 (6)
C12	1.3540 (2)	0.9576 (2)	0.11717 (18)	0.0697 (7)
H12	1.4361	0.9253	0.1240	0.084*
C13	1.2422 (2)	0.90061 (18)	0.13581 (16)	0.0582 (6)
H13	1.2496	0.8293	0.1560	0.070*
C14	0.5983 (2)	0.54440 (17)	0.14437 (14)	0.0528 (5)
C15	0.5918 (3)	0.36793 (19)	0.0794 (2)	0.0798 (8)
H15A	0.5018	0.3795	0.0559	0.096*
H15B	0.5915	0.3282	0.1385	0.096*
C16	0.6626 (3)	0.3076 (2)	0.0104 (2)	0.0967 (10)
H16A	0.6615	0.3474	−0.0479	0.145*
H16B	0.6213	0.2387	−0.0007	0.145*
H16C	0.7515	0.2970	0.0342	0.145*
C17	0.8973 (2)	1.01576 (17)	0.25156 (16)	0.0608 (6)
H17	0.9825	1.0513	0.2477	0.073*
C18	0.8868 (3)	0.9822 (2)	0.35314 (18)	0.0803 (8)
H18A	0.8993	1.0451	0.3935	0.096*
H18B	0.7994	0.9545	0.3610	0.096*
C19	0.9833 (3)	0.8994 (3)	0.38342 (18)	0.0906 (9)
H19A	0.9644	0.8337	0.3492	0.136*
H19B	0.9789	0.8864	0.4500	0.136*
H19C	1.0696	0.9240	0.3708	0.136*
C20	0.7917 (3)	1.0977 (2)	0.2147 (3)	0.0974 (10)
H20A	0.7997	1.1099	0.1483	0.146*
H20B	0.8036	1.1647	0.2483	0.146*
H20C	0.7062	1.0693	0.2246	0.146*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0832 (11)	0.1053 (12)	0.1309 (14)	−0.0492 (9)	0.0352 (10)	0.0009 (10)
O1	0.0610 (10)	0.0656 (11)	0.1054 (13)	−0.0198 (8)	0.0281 (9)	−0.0043 (9)
O2	0.0676 (10)	0.0470 (9)	0.0966 (11)	−0.0210 (7)	0.0245 (9)	−0.0150 (8)
N1	0.0434 (9)	0.0390 (9)	0.0552 (9)	−0.0022 (7)	0.0100 (7)	−0.0086 (7)
N2	0.0453 (9)	0.0410 (9)	0.0558 (9)	−0.0032 (7)	0.0156 (7)	−0.0043 (7)
C1	0.0423 (10)	0.0366 (10)	0.0481 (10)	−0.0005 (8)	0.0095 (8)	−0.0007 (8)
C2	0.0474 (10)	0.0364 (10)	0.0545 (11)	0.0001 (8)	0.0126 (9)	−0.0029 (8)
C3	0.0445 (10)	0.0431 (11)	0.0530 (11)	−0.0042 (8)	0.0072 (8)	0.0024 (8)
C4	0.0403 (10)	0.0556 (12)	0.0666 (12)	−0.0026 (9)	0.0145 (9)	−0.0033 (10)
C5	0.0450 (11)	0.0503 (12)	0.0686 (13)	0.0014 (9)	0.0146 (9)	−0.0131 (10)
C6	0.0419 (10)	0.0385 (10)	0.0519 (10)	0.0004 (8)	0.0072 (8)	−0.0039 (8)
C7	0.0449 (10)	0.0394 (10)	0.0448 (10)	−0.0021 (8)	0.0074 (8)	−0.0016 (8)
C8	0.0459 (10)	0.0433 (11)	0.0446 (9)	−0.0058 (8)	0.0095 (8)	−0.0043 (8)
C9	0.0587 (13)	0.0506 (12)	0.0579 (12)	−0.0065 (10)	0.0043 (10)	0.0044 (9)
C10	0.0820 (17)	0.0535 (13)	0.0625 (13)	−0.0223 (12)	0.0088 (12)	0.0089 (10)
C11	0.0623 (14)	0.0713 (16)	0.0702 (14)	−0.0285 (12)	0.0205 (11)	−0.0040 (12)
C12	0.0474 (13)	0.0732 (16)	0.0897 (17)	−0.0075 (11)	0.0139 (11)	−0.0017 (13)
C13	0.0524 (12)	0.0505 (12)	0.0731 (14)	−0.0045 (10)	0.0143 (10)	0.0022 (10)
C14	0.0500 (12)	0.0478 (12)	0.0613 (12)	−0.0066 (9)	0.0099 (10)	0.0027 (9)
C15	0.0873 (18)	0.0516 (14)	0.1029 (19)	−0.0304 (13)	0.0256 (15)	−0.0133 (13)
C16	0.109 (2)	0.0612 (16)	0.123 (2)	−0.0270 (16)	0.0293 (19)	−0.0215 (16)
C17	0.0572 (13)	0.0468 (12)	0.0804 (15)	−0.0078 (10)	0.0197 (11)	−0.0239 (11)
C18	0.0765 (18)	0.095 (2)	0.0720 (16)	−0.0237 (15)	0.0244 (13)	−0.0351 (14)
C19	0.098 (2)	0.114 (2)	0.0592 (15)	−0.0281 (19)	0.0050 (14)	0.0001 (15)
C20	0.0765 (18)	0.0528 (15)	0.165 (3)	0.0089 (13)	0.0213 (18)	−0.0266 (16)

Geometric parameters (Å, º) top

F1—C11	1.359 (2)	C10—C11	1.363 (4)
O1—C14	1.207 (2)	C10—H10	0.9300
O2—C14	1.329 (3)	C11—C12	1.355 (4)
O2—C15	1.451 (3)	C12—C13	1.382 (3)
N1—C7	1.383 (2)	C12—H12	0.9300
N1—C6	1.384 (2)	C13—H13	0.9300
N1—C17	1.480 (2)	C15—C16	1.456 (4)
N2—C7	1.315 (2)	C15—H15A	0.9700
N2—C1	1.391 (2)	C15—H15B	0.9700
C1—C2	1.390 (3)	C16—H16A	0.9600
C1—C6	1.396 (2)	C16—H16B	0.9600
C2—C3	1.387 (3)	C16—H16C	0.9600
C2—H2	0.9300	C17—C18	1.506 (4)
C3—C4	1.397 (3)	C17—C20	1.549 (4)
C3—C14	1.474 (3)	C17—H17	0.9800
C4—C5	1.372 (3)	C18—C19	1.468 (4)
C4—H4	0.9300	C18—H18A	0.9700
C5—C6	1.396 (3)	C18—H18B	0.9700
C5—H5	0.9300	C19—H19A	0.9600
C7—C8	1.473 (3)	C19—H19B	0.9600
C8—C13	1.379 (3)	C19—H19C	0.9600
C8—C9	1.393 (3)	C20—H20A	0.9600
C9—C10	1.376 (3)	C20—H20B	0.9600
C9—H9	0.9300	C20—H20C	0.9600

C14—O2—C15	116.83 (18)	C8—C13—H13	119.4
C7—N1—C6	105.97 (14)	C12—C13—H13	119.4
C7—N1—C17	126.27 (16)	O1—C14—O2	122.46 (19)
C6—N1—C17	125.85 (16)	O1—C14—C3	124.7 (2)
C7—N2—C1	104.55 (15)	O2—C14—C3	112.79 (17)
C2—C1—N2	129.17 (16)	O2—C15—C16	107.4 (2)
C2—C1—C6	120.37 (17)	O2—C15—H15A	110.2
N2—C1—C6	110.45 (15)	C16—C15—H15A	110.2
C3—C2—C1	118.30 (17)	O2—C15—H15B	110.2
C3—C2—H2	120.8	C16—C15—H15B	110.2
C1—C2—H2	120.9	H15A—C15—H15B	108.5
C2—C3—C4	120.33 (18)	C15—C16—H16A	109.5
C2—C3—C14	121.51 (18)	C15—C16—H16B	109.5
C4—C3—C14	118.15 (18)	H16A—C16—H16B	109.5
C5—C4—C3	122.36 (19)	C15—C16—H16C	109.5
C5—C4—H4	118.8	H16A—C16—H16C	109.5
C3—C4—H4	118.8	H16B—C16—H16C	109.5
C4—C5—C6	116.93 (18)	N1—C17—C18	110.73 (18)
C4—C5—H5	121.5	N1—C17—C20	110.4 (2)
C6—C5—H5	121.5	C18—C17—C20	114.4 (2)
N1—C6—C1	105.64 (16)	N1—C17—H17	106.9
N1—C6—C5	132.65 (17)	C18—C17—H17	106.9
C1—C6—C5	121.70 (17)	C20—C17—H17	106.9
N2—C7—N1	113.38 (16)	C19—C18—C17	112.7 (2)
N2—C7—C8	122.88 (16)	C19—C18—H18A	109.1
N1—C7—C8	123.72 (16)	C17—C18—H18A	109.1
C13—C8—C9	118.32 (18)	C19—C18—H18B	109.1
C13—C8—C7	119.53 (18)	C17—C18—H18B	109.1
C9—C8—C7	122.07 (18)	H18A—C18—H18B	107.8
C10—C9—C8	120.8 (2)	C18—C19—H19A	109.5
C10—C9—H9	119.6	C18—C19—H19B	109.5
C8—C9—H9	119.6	H19A—C19—H19B	109.5
C11—C10—C9	118.5 (2)	C18—C19—H19C	109.5
C11—C10—H10	120.8	H19A—C19—H19C	109.5
C9—C10—H10	120.8	H19B—C19—H19C	109.5
C12—C11—F1	118.7 (2)	C17—C20—H20A	109.5
C12—C11—C10	122.9 (2)	C17—C20—H20B	109.5
F1—C11—C10	118.4 (2)	H20A—C20—H20B	109.5
C11—C12—C13	118.3 (2)	C17—C20—H20C	109.5
C11—C12—H12	120.9	H20A—C20—H20C	109.5
C13—C12—H12	120.9	H20B—C20—H20C	109.5
C8—C13—C12	121.2 (2)

C7—N2—C1—C2	179.31 (19)	N1—C7—C8—C13	138.2 (2)
C7—N2—C1—C6	−0.2 (2)	N2—C7—C8—C9	133.3 (2)
N2—C1—C2—C3	179.81 (18)	N1—C7—C8—C9	−45.0 (3)
C6—C1—C2—C3	−0.7 (3)	C13—C8—C9—C10	−0.4 (3)
C1—C2—C3—C4	0.4 (3)	C7—C8—C9—C10	−177.26 (18)
C1—C2—C3—C14	−178.35 (17)	C8—C9—C10—C11	0.1 (3)
C2—C3—C4—C5	0.3 (3)	C9—C10—C11—C12	0.6 (4)
C14—C3—C4—C5	179.11 (19)	C9—C10—C11—F1	−179.65 (19)
C3—C4—C5—C6	−0.7 (3)	F1—C11—C12—C13	179.3 (2)
C7—N1—C6—C1	0.10 (19)	C10—C11—C12—C13	−0.9 (4)
C17—N1—C6—C1	−164.91 (18)	C9—C8—C13—C12	0.1 (3)
C7—N1—C6—C5	−179.7 (2)	C7—C8—C13—C12	176.99 (19)
C17—N1—C6—C5	15.3 (3)	C11—C12—C13—C8	0.6 (3)
C2—C1—C6—N1	−179.50 (16)	C15—O2—C14—O1	−1.0 (3)
N2—C1—C6—N1	0.1 (2)	C15—O2—C14—C3	179.5 (2)
C2—C1—C6—C5	0.3 (3)	C2—C3—C14—O1	177.9 (2)
N2—C1—C6—C5	179.88 (18)	C4—C3—C14—O1	−1.0 (3)
C4—C5—C6—N1	−179.9 (2)	C2—C3—C14—O2	−2.6 (3)
C4—C5—C6—C1	0.4 (3)	C4—C3—C14—O2	178.55 (18)
C1—N2—C7—N1	0.3 (2)	C14—O2—C15—C16	170.5 (2)
C1—N2—C7—C8	−178.22 (16)	C7—N1—C17—C18	−110.7 (2)
C6—N1—C7—N2	−0.2 (2)	C6—N1—C17—C18	51.3 (3)
C17—N1—C7—N2	164.68 (18)	C7—N1—C17—C20	121.5 (2)
C6—N1—C7—C8	178.24 (17)	C6—N1—C17—C20	−76.5 (3)
C17—N1—C7—C8	−16.8 (3)	N1—C17—C18—C19	50.7 (3)
N2—C7—C8—C13	−43.5 (3)	C20—C17—C18—C19	176.3 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1/C7/N2/C1/C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.93	2.53	3.452 (3)	169
C20—H20C···O1ⁱ	0.96	2.59	3.485 (4)	154
C19—H19A···Cg1	0.96	2.82	3.400 (3)	121

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₁FN₂O₂
M_r	340.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.2249 (16), 12.3767 (18), 14.149 (2)
β (°)	93.473 (2)
V (Å³)	1787.3 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.37 × 0.20 × 0.11

Data collection
Diffractometer	Bruker APEXII DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.968, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	10465, 3130, 2342
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.150, 1.05
No. of reflections	3130
No. of parameters	229
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.20

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1/C7/N2/C1/C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.93	2.53	3.452 (3)	169
C20—H20C···O1ⁱ	0.96	2.59	3.485 (4)	154
C19—H19A···Cg1	0.96	2.82	3.400 (3)	121

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Acknowledgements

NA, ASAR and SAH acknowledge Universiti Sains Malaysia (USM) for funding the synthetic chemistry work under 304/PFARMASI/650544 and 304/PFARMASI/650512. NA also thanks Universiti Sains Malaysia for the award of a postdoctoral fellowship.

References

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Volume 67| Part 11| November 2011| Page o2938

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