Ethyl 2-(4-chloro­phen­yl)-1-phenyl-1H-benzimidazole-5-carboxyl­ate

Yoon, Y.K.; Manogaran, E.; Choon, T.S.; Arshad, S.; Razak, I.A.

doi:10.1107/S1600536812022192

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1863

doi:10.1107/S1600536812022192

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Ethyl 2-(4-chlorophenyl)-1-phenyl-1H-benzimidazole-5-carboxylate

Yeong Keng Yoon,^a Elumalai Manogaran,^b Tan Soo Choon,^a Suhana Arshad ^c and Ibrahim Abdul Razak ^c ^*‡

^aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, Minden 11800, Penang, Malaysia, ^bDepartment of Pharmaceutical Sciences, UCSI University, Kuala Lumpur, Cheras 56000, Malaysia, and ^cSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: arazaki@usm.my

(Received 7 May 2012; accepted 16 May 2012; online 23 May 2012)

In the title compound, C₂₂H₁₇ClN₂O₂, the essentially planar benzimidazole ring system [maximum deviation = 0.012 (2) Å] forms dihedral angles of 28.69 (6) and 63.65 (7)°, respectively, with the phenyl and chloro-substituted benzene rings. The dihedral angle between the phenyl and benzene rings is 64.23 (8)°. In the crystal, molecules are linked into a zigzag chain along the a axis by intermolecular C—H⋯O hydrogen bonds. C—H⋯π interactions are also present.

Related literature

For applications of benzimidazoles, see: Tanious et al. (2004 ); Townsend & Revankar (1970 ). For related structures, see: Yoon et al. (2011 , 2012 ); Kassim et al. (2012 ). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₂H₁₇ClN₂O₂
M_r = 376.83
Triclinic, $[P \overline 1]$
a = 9.3357 (2) Å
b = 9.7982 (2) Å
c = 11.7718 (4) Å
α = 107.502 (2)°
β = 102.106 (2)°
γ = 109.539 (1)°
V = 908.31 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 100 K
0.38 × 0.29 × 0.24 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.917, T_max = 0.946
18472 measured reflections
5326 independent reflections
4233 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.127
S = 1.04
5326 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the N1/C7/N2/C1/C6, C1–C6 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O2ⁱ	0.95	2.39	3.324 (2)	166
C21—H21A⋯Cg1ⁱⁱ	0.99	2.63	3.5183 (16)	149
C12—H12A⋯Cg2ⁱⁱⁱ	0.95	2.96	3.5940 (16)	125
C19—H19A⋯Cg3ⁱⁱⁱ	0.95	2.60	3.4770 (18)	153
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y, -z+1; (iii) -x, -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 global, I. DOI: 10.1107/S1600536812022192/is5137sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812022192/is5137Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812022192/is5137Isup3.cml

checkCIF report

Comment top

Substituted benzimidazoles are proven important drug leads. Substituted benzimidazole is the key building block for numerous compounds which plays crucial roles in the function of biologically important molecules (Tanious et al., 2004). In particular, 2-substituted benzimidazoles are recognized as potential anticancer agents (Townsend & Revankar, 1970). As part of our ongoing structural studies of benzimidazole derivatives (Yoon et al., 2011), we now report the structure of the title compound.

In the molecular structure (Fig. 1), The benzimidazole ring system (N1/N2/C1—C7) is essentially planar with a maximum deviation of 0.012 (2) Å at atom C1 and forms dihedral angles of 28.69 (6) and 63.65 (7)°, respectively, with the phenyl (C8–C13) and chloro-substituted benzene (C14–C19) ring. The dihedral angle between the phenyl ring and the chloro-substituted benzene ring is 64.23 (8)°. Bond lengths and angles are within normal ranges and are comparable to related structures (Yoon et al., 2011; Kassim et al., 2012; Yoon et al., 2012).

The crystal packing is shown in Fig. 2. The molecules are linked into a zigzag chain along the a-axis via intermolecular C15—H15A···O2 (Table 1) hydrogen bonds. The crystal structure is further stabilized by intermolecular C21—H21A···Cg1, C1—H12A···Cg2 and C19—H19A···Cg3 (Table 1) interactions (Cg1, Cg2 and Cg3 are the centroids of N1/N2/C1/C6/C7, C1–C6 and C8–C13 rings, respectively).

Related literature top

For applications of benzimidazoles, see: Tanious et al. (2004); Townsend & Revankar (1970). For related structures, see: Yoon et al. (2011, 2012); Kassim et al. (2012). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

Ethyl 3-amino-4-(phenyl amino) benzoate (0.84 mmol) and sodium metabisulfite adduct of chlorobenzaldehyde (1.68 mmol) were dissolved in DMF. The reaction mixture was reflux at 130 °C for 2 h. After completion, the reaction mixture was diluted in ethyl acetate (20 ml) and washed with water (20 ml). The organic layer was collected, dried over Na₂SO₄ and the evaporated in-vacuo to yield the product. The product was recrystallized from ethyl acetate.

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 and the atom-numbering scheme.
	Fig. 2. A crystal packing diagram of the title compound viewed along the b axis. The H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

Ethyl 2-(4-chlorophenyl)-1-phenyl-1H-benzimidazole-5-carboxylate top

Crystal data top

C₂₂H₁₇ClN₂O₂	Z = 2
M_r = 376.83	F(000) = 392
Triclinic, P1	D_x = 1.378 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3357 (2) Å	Cell parameters from 7225 reflections
b = 9.7982 (2) Å	θ = 2.6–30.2°
c = 11.7718 (4) Å	µ = 0.23 mm⁻¹
α = 107.502 (2)°	T = 100 K
β = 102.106 (2)°	Block, colourless
γ = 109.539 (1)°	0.38 × 0.29 × 0.24 mm
V = 908.31 (4) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5326 independent reflections
Radiation source: fine-focus sealed tube	4233 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scans	θ_max = 30.2°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
T_min = 0.917, T_max = 0.946	k = −13→13
18472 measured reflections	l = −14→16

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) = 0.127	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0648P)² + 0.3753P] where P = (F_o² + 2F_c²)/3
5326 reflections	(Δ/σ)_max < 0.001
245 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₂H₁₇ClN₂O₂	γ = 109.539 (1)°
M_r = 376.83	V = 908.31 (4) Å³
Triclinic, P1	Z = 2
a = 9.3357 (2) Å	Mo Kα radiation
b = 9.7982 (2) Å	µ = 0.23 mm⁻¹
c = 11.7718 (4) Å	T = 100 K
α = 107.502 (2)°	0.38 × 0.29 × 0.24 mm
β = 102.106 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5326 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4233 reflections with I > 2σ(I)
T_min = 0.917, T_max = 0.946	R_int = 0.033
18472 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.04	Δρ_max = 0.57 e Å⁻³
5326 reflections	Δρ_min = −0.31 e Å⁻³
245 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 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
Cl1	−0.66895 (5)	−0.31206 (5)	−0.07003 (4)	0.02705 (11)
O1	0.66316 (12)	−0.10624 (12)	0.40052 (10)	0.0196 (2)
O2	0.84606 (13)	0.14573 (13)	0.46871 (11)	0.0229 (2)
N1	0.11793 (15)	−0.10887 (14)	0.20878 (12)	0.0173 (2)
N2	0.16095 (14)	0.14100 (14)	0.23348 (12)	0.0158 (2)
C1	0.31182 (17)	0.14553 (17)	0.28366 (14)	0.0165 (3)
C2	0.46660 (18)	0.26942 (17)	0.34187 (14)	0.0190 (3)
H2A	0.4848	0.3744	0.3520	0.023*
C3	0.59248 (18)	0.23218 (18)	0.38427 (15)	0.0201 (3)
H3A	0.6997	0.3136	0.4249	0.024*
C4	0.56507 (17)	0.07571 (17)	0.36849 (14)	0.0179 (3)
C5	0.41041 (18)	−0.04706 (17)	0.31022 (14)	0.0180 (3)
H5A	0.3924	−0.1521	0.2997	0.022*
C6	0.28203 (17)	−0.01073 (17)	0.26755 (13)	0.0165 (3)
C7	0.04967 (17)	−0.01571 (16)	0.19011 (13)	0.0159 (3)
C8	−0.12637 (17)	−0.07740 (17)	0.12872 (13)	0.0158 (3)
C9	−0.22379 (18)	−0.21369 (17)	0.13982 (14)	0.0178 (3)
H9A	−0.1746	−0.2585	0.1881	0.021*
C10	−0.39041 (19)	−0.28384 (18)	0.08158 (14)	0.0199 (3)
H10A	−0.4559	−0.3739	0.0919	0.024*
C11	−0.46027 (18)	−0.21990 (18)	0.00743 (14)	0.0192 (3)
C12	−0.36672 (18)	−0.08703 (18)	−0.00704 (14)	0.0186 (3)
H12A	−0.4161	−0.0458	−0.0588	0.022*
C13	−0.19981 (18)	−0.01465 (17)	0.05489 (13)	0.0171 (3)
H13A	−0.1354	0.0779	0.0470	0.021*
C14	0.13273 (17)	0.27784 (17)	0.23909 (13)	0.0163 (3)
C15	0.04178 (18)	0.32176 (18)	0.31023 (14)	0.0188 (3)
H15A	−0.0040	0.2607	0.3534	0.023*
C16	0.01898 (19)	0.45680 (19)	0.31695 (15)	0.0223 (3)
H16A	−0.0417	0.4888	0.3661	0.027*
C17	0.0840 (2)	0.54544 (18)	0.25259 (16)	0.0242 (3)
H17A	0.0675	0.6374	0.2577	0.029*
C18	0.1728 (2)	0.49899 (19)	0.18094 (16)	0.0246 (3)
H18A	0.2161	0.5586	0.1360	0.029*
C19	0.19904 (19)	0.36522 (18)	0.17450 (14)	0.0204 (3)
H19A	0.2614	0.3343	0.1266	0.024*
C20	0.70739 (18)	0.04619 (17)	0.41852 (14)	0.0171 (3)
C21	0.79321 (18)	−0.14740 (18)	0.44432 (14)	0.0188 (3)
H21A	0.8447	−0.0928	0.5378	0.023*
H21B	0.8767	−0.1165	0.4056	0.023*
C22	0.7175 (2)	−0.32370 (19)	0.40427 (16)	0.0254 (3)
H22A	0.8013	−0.3578	0.4317	0.038*
H22B	0.6667	−0.3759	0.3117	0.038*
H22C	0.6354	−0.3523	0.4433	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.01444 (18)	0.0278 (2)	0.0327 (2)	0.00672 (15)	0.00290 (15)	0.01040 (16)
O1	0.0137 (5)	0.0191 (5)	0.0244 (5)	0.0072 (4)	0.0042 (4)	0.0082 (4)
O2	0.0151 (5)	0.0228 (5)	0.0280 (6)	0.0061 (5)	0.0055 (4)	0.0100 (5)
N1	0.0149 (6)	0.0164 (6)	0.0196 (6)	0.0061 (5)	0.0041 (5)	0.0077 (5)
N2	0.0141 (6)	0.0151 (5)	0.0192 (6)	0.0060 (5)	0.0063 (5)	0.0079 (5)
C1	0.0151 (6)	0.0175 (6)	0.0181 (6)	0.0073 (6)	0.0064 (5)	0.0081 (5)
C2	0.0180 (7)	0.0154 (6)	0.0228 (7)	0.0060 (6)	0.0073 (6)	0.0078 (6)
C3	0.0152 (7)	0.0189 (7)	0.0237 (7)	0.0049 (6)	0.0067 (6)	0.0082 (6)
C4	0.0152 (7)	0.0201 (7)	0.0187 (7)	0.0073 (6)	0.0056 (5)	0.0084 (6)
C5	0.0169 (7)	0.0170 (6)	0.0206 (7)	0.0074 (6)	0.0064 (6)	0.0080 (5)
C6	0.0155 (6)	0.0163 (6)	0.0173 (6)	0.0062 (6)	0.0059 (5)	0.0067 (5)
C7	0.0163 (6)	0.0150 (6)	0.0156 (6)	0.0057 (6)	0.0053 (5)	0.0064 (5)
C8	0.0144 (6)	0.0159 (6)	0.0152 (6)	0.0062 (5)	0.0042 (5)	0.0045 (5)
C9	0.0177 (7)	0.0179 (6)	0.0172 (6)	0.0069 (6)	0.0057 (5)	0.0073 (5)
C10	0.0190 (7)	0.0202 (7)	0.0194 (7)	0.0066 (6)	0.0076 (6)	0.0080 (6)
C11	0.0140 (6)	0.0224 (7)	0.0180 (7)	0.0076 (6)	0.0047 (5)	0.0048 (6)
C12	0.0182 (7)	0.0217 (7)	0.0177 (7)	0.0114 (6)	0.0058 (5)	0.0071 (5)
C13	0.0183 (7)	0.0170 (6)	0.0176 (7)	0.0082 (6)	0.0072 (5)	0.0075 (5)
C14	0.0161 (6)	0.0151 (6)	0.0169 (6)	0.0065 (6)	0.0040 (5)	0.0066 (5)
C15	0.0172 (7)	0.0196 (7)	0.0190 (7)	0.0074 (6)	0.0058 (6)	0.0076 (6)
C16	0.0189 (7)	0.0221 (7)	0.0254 (8)	0.0111 (6)	0.0068 (6)	0.0067 (6)
C17	0.0225 (8)	0.0173 (7)	0.0295 (8)	0.0094 (6)	0.0027 (6)	0.0086 (6)
C18	0.0305 (8)	0.0183 (7)	0.0253 (8)	0.0089 (7)	0.0084 (7)	0.0119 (6)
C19	0.0240 (8)	0.0191 (7)	0.0202 (7)	0.0092 (6)	0.0099 (6)	0.0090 (6)
C20	0.0154 (6)	0.0198 (7)	0.0181 (7)	0.0078 (6)	0.0081 (5)	0.0083 (5)
C21	0.0154 (7)	0.0219 (7)	0.0198 (7)	0.0097 (6)	0.0049 (5)	0.0081 (6)
C22	0.0282 (8)	0.0247 (8)	0.0256 (8)	0.0139 (7)	0.0083 (7)	0.0110 (6)

Geometric parameters (Å, º) top

Cl1—C11	1.7393 (15)	C10—C11	1.394 (2)
O1—C20	1.3440 (17)	C10—H10A	0.9500
O1—C21	1.4466 (17)	C11—C12	1.386 (2)
O2—C20	1.2101 (18)	C12—C13	1.391 (2)
N1—C7	1.3186 (18)	C12—H12A	0.9500
N1—C6	1.3858 (19)	C13—H13A	0.9500
N2—C1	1.3885 (17)	C14—C19	1.389 (2)
N2—C7	1.3916 (18)	C14—C15	1.390 (2)
N2—C14	1.4359 (17)	C15—C16	1.391 (2)
C1—C2	1.394 (2)	C15—H15A	0.9500
C1—C6	1.4057 (19)	C16—C17	1.390 (2)
C2—C3	1.383 (2)	C16—H16A	0.9500
C2—H2A	0.9500	C17—C18	1.386 (2)
C3—C4	1.413 (2)	C17—H17A	0.9500
C3—H3A	0.9500	C18—C19	1.395 (2)
C4—C5	1.389 (2)	C18—H18A	0.9500
C4—C20	1.4923 (19)	C19—H19A	0.9500
C5—C6	1.3985 (19)	C21—C22	1.503 (2)
C5—H5A	0.9500	C21—H21A	0.9900
C7—C8	1.471 (2)	C21—H21B	0.9900
C8—C13	1.3990 (19)	C22—H22A	0.9800
C8—C9	1.403 (2)	C22—H22B	0.9800
C9—C10	1.384 (2)	C22—H22C	0.9800
C9—H9A	0.9500

C20—O1—C21	115.83 (11)	C11—C12—H12A	120.3
C7—N1—C6	105.12 (12)	C13—C12—H12A	120.3
C1—N2—C7	106.08 (11)	C12—C13—C8	120.38 (14)
C1—N2—C14	124.39 (12)	C12—C13—H13A	119.8
C7—N2—C14	129.30 (12)	C8—C13—H13A	119.8
N2—C1—C2	131.98 (13)	C19—C14—C15	121.23 (13)
N2—C1—C6	105.41 (12)	C19—C14—N2	119.15 (13)
C2—C1—C6	122.60 (13)	C15—C14—N2	119.61 (13)
C3—C2—C1	116.80 (13)	C14—C15—C16	118.77 (14)
C3—C2—H2A	121.6	C14—C15—H15A	120.6
C1—C2—H2A	121.6	C16—C15—H15A	120.6
C2—C3—C4	121.44 (14)	C17—C16—C15	120.81 (14)
C2—C3—H3A	119.3	C17—C16—H16A	119.6
C4—C3—H3A	119.3	C15—C16—H16A	119.6
C5—C4—C3	121.36 (13)	C18—C17—C16	119.67 (14)
C5—C4—C20	120.65 (13)	C18—C17—H17A	120.2
C3—C4—C20	117.98 (13)	C16—C17—H17A	120.2
C4—C5—C6	117.73 (13)	C17—C18—C19	120.38 (15)
C4—C5—H5A	121.1	C17—C18—H18A	119.8
C6—C5—H5A	121.1	C19—C18—H18A	119.8
N1—C6—C5	129.46 (13)	C14—C19—C18	119.13 (14)
N1—C6—C1	110.46 (12)	C14—C19—H19A	120.4
C5—C6—C1	120.07 (13)	C18—C19—H19A	120.4
N1—C7—N2	112.93 (12)	O2—C20—O1	123.55 (13)
N1—C7—C8	121.50 (13)	O2—C20—C4	124.85 (13)
N2—C7—C8	125.57 (12)	O1—C20—C4	111.60 (12)
C13—C8—C9	118.95 (13)	O1—C21—C22	106.27 (12)
C13—C8—C7	124.14 (13)	O1—C21—H21A	110.5
C9—C8—C7	116.79 (12)	C22—C21—H21A	110.5
C10—C9—C8	121.07 (13)	O1—C21—H21B	110.5
C10—C9—H9A	119.5	C22—C21—H21B	110.5
C8—C9—H9A	119.5	H21A—C21—H21B	108.7
C9—C10—C11	118.76 (14)	C21—C22—H22A	109.5
C9—C10—H10A	120.6	C21—C22—H22B	109.5
C11—C10—H10A	120.6	H22A—C22—H22B	109.5
C12—C11—C10	121.37 (14)	C21—C22—H22C	109.5
C12—C11—Cl1	119.89 (11)	H22A—C22—H22C	109.5
C10—C11—Cl1	118.73 (12)	H22B—C22—H22C	109.5
C11—C12—C13	119.42 (13)

C7—N2—C1—C2	−178.88 (15)	C13—C8—C9—C10	−1.5 (2)
C14—N2—C1—C2	−4.0 (2)	C7—C8—C9—C10	−177.72 (13)
C7—N2—C1—C6	−0.11 (15)	C8—C9—C10—C11	2.2 (2)
C14—N2—C1—C6	174.80 (13)	C9—C10—C11—C12	−1.1 (2)
N2—C1—C2—C3	178.50 (15)	C9—C10—C11—Cl1	177.86 (11)
C6—C1—C2—C3	−0.1 (2)	C10—C11—C12—C13	−0.8 (2)
C1—C2—C3—C4	0.3 (2)	Cl1—C11—C12—C13	−179.71 (11)
C2—C3—C4—C5	−0.3 (2)	C11—C12—C13—C8	1.5 (2)
C2—C3—C4—C20	−179.22 (14)	C9—C8—C13—C12	−0.4 (2)
C3—C4—C5—C6	−0.1 (2)	C7—C8—C13—C12	175.52 (13)
C20—C4—C5—C6	178.85 (13)	C1—N2—C14—C19	65.11 (19)
C7—N1—C6—C5	179.06 (15)	C7—N2—C14—C19	−121.21 (16)
C7—N1—C6—C1	−0.26 (16)	C1—N2—C14—C15	−114.00 (16)
C4—C5—C6—N1	−178.95 (14)	C7—N2—C14—C15	59.7 (2)
C4—C5—C6—C1	0.3 (2)	C19—C14—C15—C16	−0.6 (2)
N2—C1—C6—N1	0.23 (16)	N2—C14—C15—C16	178.49 (13)
C2—C1—C6—N1	179.15 (13)	C14—C15—C16—C17	0.8 (2)
N2—C1—C6—C5	−179.16 (13)	C15—C16—C17—C18	−0.1 (2)
C2—C1—C6—C5	−0.2 (2)	C16—C17—C18—C19	−0.8 (2)
C6—N1—C7—N2	0.19 (16)	C15—C14—C19—C18	−0.3 (2)
C6—N1—C7—C8	179.89 (13)	N2—C14—C19—C18	−179.41 (14)
C1—N2—C7—N1	−0.05 (16)	C17—C18—C19—C14	1.0 (2)
C14—N2—C7—N1	−174.62 (13)	C21—O1—C20—O2	−0.5 (2)
C1—N2—C7—C8	−179.73 (13)	C21—O1—C20—C4	179.16 (12)
C14—N2—C7—C8	5.7 (2)	C5—C4—C20—O2	178.84 (15)
N1—C7—C8—C13	−149.37 (15)	C3—C4—C20—O2	−2.2 (2)
N2—C7—C8—C13	30.3 (2)	C5—C4—C20—O1	−0.83 (19)
N1—C7—C8—C9	26.6 (2)	C3—C4—C20—O1	178.10 (13)
N2—C7—C8—C9	−153.74 (14)	C20—O1—C21—C22	−175.16 (12)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the N1/C7/N2/C1/C6, C1–C6 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O2ⁱ	0.95	2.39	3.324 (2)	166
C21—H21A···Cg1ⁱⁱ	0.99	2.63	3.5183 (16)	149
C12—H12A···Cg2ⁱⁱⁱ	0.95	2.96	3.5940 (16)	125
C19—H19A···Cg3ⁱⁱⁱ	0.95	2.60	3.4770 (18)	153

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₇ClN₂O₂
M_r	376.83
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.3357 (2), 9.7982 (2), 11.7718 (4)
α, β, γ (°)	107.502 (2), 102.106 (2), 109.539 (1)
V (Å³)	908.31 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.38 × 0.29 × 0.24

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.917, 0.946
No. of measured, independent and observed [I > 2σ(I)] reflections	18472, 5326, 4233
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.708

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.127, 1.04
No. of reflections	5326
No. of parameters	245
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.31

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

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2 and Cg3 are the centroids of the N1/C7/N2/C1/C6, C1–C6 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O2ⁱ	0.95	2.39	3.324 (2)	166
C21—H21A···Cg1ⁱⁱ	0.99	2.63	3.5183 (16)	149
C12—H12A···Cg2ⁱⁱⁱ	0.95	2.96	3.5940 (16)	125
C19—H19A···Cg3ⁱⁱⁱ	0.95	2.60	3.4770 (18)	153

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

Footnotes

‡Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the Research University Grant Nos.1001/PFIZIK/811151 and 1001/PSK/8620012. The authors also wish to express their thanks to the Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Molecular Medicine, Universiti Sains Malaysia. SA also thanks the Malaysian Government and USM for an Academic Staff Training Scheme (ASTS) fellowship.

References

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