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

Arumugam, N.; Abdul Rahim, A.S.; Osman, H.; Quah, C.K.; Fun, H.-K.

doi:10.1107/S1600536810033945

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 9| September 2010| Pages o2412-o2413

https://doi.org/10.1107/S1600536810033945

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

Natarajan Arumugam,^a Aisyah Saad Abdul Rahim,^a ‡ Hasnah Osman,^b Ching Kheng Quah ^c § and Hoong-Kun Fun ^c ^*¶

^aSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 20 August 2010; accepted 23 August 2010; online 28 August 2010)

In the title compound, C₂₀H₂₁ClN₂O₂, the ethyl 1H-benzimidazole-5-carboxylate ring system, excluding the methylene and methyl H atoms, is almost planar, with a maximum deviation of 0.055 (1) Å, and makes a dihedral angle of 40.63 (4)° with the benzene ring. The sec-butyl group is disordered over two positions, with refined site occupancies of 0.855 (4) and 0.145 (4). In the crystal, molecules are linked into chains along [010] via intermolecular C—H⋯O hydrogen bonds and are further interconnected by C—H⋯Cl interactions into two-dimensional networks parallel to (001). The crystal structure is further consolidated by C—H⋯π interactions.

Related literature

For the synthesis of the title compound, see: Arumugam et al. (2010a ,b ,c ). For general background to and the therapeutic properties of benzimidazole derivatives, see: Bonfanti et al. (2008 ); Evans et al. (1997 ); Hori et al. (2002 ); Snow (2007 ). For a related structure, see: Eltayeb et al. (2009 ). For reference bond lengths, see: Allen et al. (1987 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₂₀H₂₁ClN₂O₂
M_r = 356.84
Monoclinic, P 2₁ /c
a = 10.4321 (9) Å
b = 12.6218 (12) Å
c = 13.6896 (12) Å
β = 97.043 (3)°
V = 1788.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 100 K
0.45 × 0.34 × 0.10 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.904, T_max = 0.977
21234 measured reflections
8437 independent reflections
6651 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.175
S = 1.09
8437 reflections
248 parameters
H-atom parameters constrained
Δρ_max = 0.75 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C7/N2/C13/C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12A⋯O2ⁱ	0.93	2.57	3.4994 (16)	174
C16—H16A⋯Cl1ⁱⁱ	0.96	2.73	3.4651 (17)	134
C19A—H19B⋯Cg1	0.96	2.71	3.3457 (18)	124
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x-1, y+1, 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: https://doi.org/10.1107/S1600536810033945/wn2406sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810033945/wn2406Isup2.hkl

checkCIF report

Comment top

Benzimidazole is an important pharmacophore in drug discovery and its derivatives have shown various therapeutic properties such as antiviral (Bonfanti et al., 2008) and anti-HIV-1 (Evans et al., 1997) activities. Benzimidazoles are used as biomimetics of guanine residues and selectively inhibit endothelial cell growth and suppress angiogenesis in vitro and in vivo (Hori et al., 2002). In particular, substituted benzimidazole derivatives are also inhibitors of tyrosine kinase and are useful for inhibiting cell proliferation for the treatment of cancer (Snow et al., 2007). In view of their importance, the crystal structure determination of the title compound was carried out and the results are presented here.

The molecular structure of the title compound is shown in Fig. 1. The ethyl 1H-benzimidazole-5-carboxylate ring system (O1/O2/N1/N2/C7–C16), excluding methylene and methyl H atoms, is almost planar, with a maximum deviation of 0.055 (1) Å for atom O2, and makes a dihedral angle of 40.63 (4)° with the benzene (C1–C6) ring. The sec-butyl group is disordered over two positions with refined site-occupancies of 0.855 (4) and 0.145 (4). The bond lengths (Allen et al., 1987) and angles in the title compound are within normal ranges and comparable to those in a related crystal structure (Eltayeb et al., 2009).

In the crystal structure (Fig. 2), the molecules are linked into one-dimensional chains along [010] via intermolecular C12—H12A···O2 hydrogen bonds and are further interconnected by C16–H16A···Cl1 interactions into two-dimensional networks parallel to (001). The crystal structure is further consolidated by C—H···Cg1 (Table 1) interactions; Cg1 is the centroid of the N1/C7/N2/C13/C8 ring.

Related literature top

For the synthesis of the title compound, see: Arumugam et al. (2010a,b,c). For general background to and the therapeutic properties of benzimidazole derivatives, see: Bonfanti et al. (2008); Evans et al. (1997); Hori et al. (2002); Snow (2007). For a related structure, see: Eltayeb et al. (2009). For reference bond lengths, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound was synthesized using previously reported procedures (Arumugam et al., 2010a,b,c). The crude product was recrystallized from ethyl acetate to yield the title compound as colourless crystals.

Structure description top

For the synthesis of the title compound, see: Arumugam et al. (2010a,b,c). For general background to and the therapeutic properties of benzimidazole derivatives, see: Bonfanti et al. (2008); Evans et al. (1997); Hori et al. (2002); Snow (2007). For a related structure, see: Eltayeb et al. (2009). For reference bond lengths, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

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 for non-H atoms and the atom-numbering scheme. Both disorder components are shown; atom labels with suffix A correspond to the major disorder component, while those with suffix B correspond to the minor disorder component.
	Fig. 2. The crystal structure of the title compound, viewed along the c axis. H atoms not involved in intermolecular interactions (dashed lines) and the minor disorder component have been omitted for clarity.

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

Crystal data top

C₂₀H₂₁ClN₂O₂	F(000) = 752
M_r = 356.84	D_x = 1.325 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5929 reflections
a = 10.4321 (9) Å	θ = 2.8–36.1°
b = 12.6218 (12) Å	µ = 0.23 mm⁻¹
c = 13.6896 (12) Å	T = 100 K
β = 97.043 (3)°	Plate, colourless
V = 1788.9 (3) Å³	0.45 × 0.34 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	8437 independent reflections
Radiation source: fine-focus sealed tube	6651 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
φ and ω scans	θ_max = 36.2°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→17
T_min = 0.904, T_max = 0.977	k = −14→20
21234 measured reflections	l = −22→22

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.175	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0914P)² + 0.4364P] where P = (F_o² + 2F_c²)/3
8437 reflections	(Δ/σ)_max < 0.001
248 parameters	Δρ_max = 0.75 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₂₀H₂₁ClN₂O₂	V = 1788.9 (3) Å³
M_r = 356.84	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.4321 (9) Å	µ = 0.23 mm⁻¹
b = 12.6218 (12) Å	T = 100 K
c = 13.6896 (12) Å	0.45 × 0.34 × 0.10 mm
β = 97.043 (3)°

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	8437 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	6651 reflections with I > 2σ(I)
T_min = 0.904, T_max = 0.977	R_int = 0.038
21234 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.175	H-atom parameters constrained
S = 1.09	Δρ_max = 0.75 e Å⁻³
8437 reflections	Δρ_min = −0.39 e Å⁻³
248 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems 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	Occ. (<1)
Cl1	1.44482 (3)	−0.12780 (3)	0.05943 (3)	0.02804 (10)
O1	0.66151 (9)	0.53169 (7)	0.09366 (8)	0.02287 (19)
O2	0.49447 (10)	0.47833 (8)	0.17101 (8)	0.0244 (2)
N1	0.97430 (9)	0.22053 (7)	0.11935 (8)	0.01566 (17)
N2	0.88205 (10)	0.08363 (8)	0.19214 (8)	0.01724 (18)
C1	1.08637 (12)	−0.04972 (9)	0.10289 (9)	0.0184 (2)
H1A	1.0056	−0.0819	0.0969	0.022*
C2	1.19323 (13)	−0.10669 (10)	0.08102 (9)	0.0198 (2)
H2A	1.1846	−0.1769	0.0607	0.024*
C3	1.31246 (12)	−0.05767 (10)	0.08982 (9)	0.0193 (2)
C4	1.32851 (12)	0.04663 (10)	0.12105 (10)	0.0204 (2)
H4A	1.4096	0.0782	0.1271	0.025*
C5	1.22138 (12)	0.10309 (9)	0.14312 (9)	0.0186 (2)
H5A	1.2310	0.1730	0.1643	0.022*
C6	1.09949 (11)	0.05585 (9)	0.13384 (8)	0.01582 (18)
C7	0.98702 (11)	0.12116 (9)	0.14997 (8)	0.01543 (18)
C8	0.85402 (10)	0.25092 (8)	0.14249 (8)	0.01417 (17)
C9	0.79079 (11)	0.34784 (9)	0.12560 (8)	0.01504 (18)
H9A	0.8286	0.4032	0.0947	0.018*
C10	0.66963 (11)	0.35881 (8)	0.15650 (8)	0.01520 (18)
C11	0.61175 (11)	0.27463 (9)	0.20282 (9)	0.0176 (2)
H11A	0.5306	0.2846	0.2229	0.021*
C12	0.67240 (12)	0.17741 (9)	0.21918 (9)	0.0187 (2)
H12A	0.6338	0.1219	0.2493	0.022*
C13	0.79468 (11)	0.16691 (9)	0.18806 (8)	0.01594 (19)
C14	0.59808 (11)	0.46053 (9)	0.14271 (9)	0.01683 (19)
C15	0.60047 (14)	0.63413 (10)	0.07588 (11)	0.0256 (3)
H15A	0.6041	0.6740	0.1367	0.031*
H15B	0.5107	0.6256	0.0489	0.031*
C16	0.67404 (16)	0.69051 (12)	0.00368 (13)	0.0320 (3)
H16A	0.6341	0.7577	−0.0131	0.048*
H16B	0.6735	0.6483	−0.0547	0.048*
H16C	0.7615	0.7016	0.0327	0.048*
C17A	0.87973 (15)	−0.01159 (11)	0.25461 (12)	0.0170 (3)	0.855 (4)
H17A	0.9624	−0.0480	0.2532	0.020*	0.855 (4)
C18A	0.87305 (16)	0.02241 (14)	0.36090 (11)	0.0228 (3)	0.855 (4)
H18A	0.7882	0.0516	0.3663	0.027*	0.855 (4)
H18B	0.8847	−0.0393	0.4034	0.027*	0.855 (4)
C19A	0.97501 (17)	0.10445 (16)	0.39550 (12)	0.0268 (4)	0.855 (4)
H19A	0.9705	0.1207	0.4635	0.040*	0.855 (4)
H19B	0.9599	0.1676	0.3568	0.040*	0.855 (4)
H19C	1.0590	0.0768	0.3881	0.040*	0.855 (4)
C20A	0.77336 (17)	−0.08965 (12)	0.21576 (16)	0.0277 (4)	0.855 (4)
H20A	0.7817	−0.1070	0.1486	0.042*	0.855 (4)
H20B	0.6904	−0.0579	0.2194	0.042*	0.855 (4)
H20C	0.7812	−0.1529	0.2549	0.042*	0.855 (4)
C17B	0.9122 (10)	0.0082 (8)	0.2857 (7)	0.0179 (16)*	0.145 (4)
H17B	0.9924	−0.0301	0.2791	0.021*	0.145 (4)
C18B	0.8027 (10)	−0.0706 (8)	0.2733 (8)	0.027 (2)*	0.145 (4)
H18C	0.7234	−0.0335	0.2817	0.032*	0.145 (4)
H18D	0.8175	−0.1225	0.3257	0.032*	0.145 (4)
C19B	0.7823 (14)	−0.1313 (11)	0.1720 (11)	0.039 (3)*	0.145 (4)
H19D	0.7234	−0.1891	0.1764	0.059*	0.145 (4)
H19E	0.8636	−0.1582	0.1569	0.059*	0.145 (4)
H19F	0.7472	−0.0836	0.1210	0.059*	0.145 (4)
C20B	0.9247 (12)	0.0562 (10)	0.3823 (8)	0.027 (2)*	0.145 (4)
H20D	0.9400	0.0021	0.4316	0.040*	0.145 (4)
H20E	0.8466	0.0934	0.3909	0.040*	0.145 (4)
H20F	0.9959	0.1050	0.3886	0.040*	0.145 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.02775 (17)	0.02678 (16)	0.03220 (17)	0.01538 (12)	0.01408 (13)	0.00528 (12)
O1	0.0225 (4)	0.0148 (4)	0.0334 (5)	0.0082 (3)	0.0119 (4)	0.0077 (3)
O2	0.0204 (4)	0.0219 (4)	0.0331 (5)	0.0080 (3)	0.0115 (4)	0.0027 (4)
N1	0.0143 (4)	0.0123 (3)	0.0216 (4)	0.0030 (3)	0.0068 (3)	0.0023 (3)
N2	0.0176 (4)	0.0122 (4)	0.0236 (4)	0.0040 (3)	0.0091 (3)	0.0050 (3)
C1	0.0196 (5)	0.0148 (4)	0.0209 (5)	0.0035 (4)	0.0035 (4)	0.0002 (4)
C2	0.0244 (5)	0.0156 (4)	0.0200 (5)	0.0062 (4)	0.0052 (4)	−0.0001 (4)
C3	0.0211 (5)	0.0189 (5)	0.0189 (5)	0.0093 (4)	0.0070 (4)	0.0035 (4)
C4	0.0175 (5)	0.0192 (5)	0.0256 (5)	0.0044 (4)	0.0068 (4)	0.0022 (4)
C5	0.0178 (5)	0.0153 (4)	0.0237 (5)	0.0031 (4)	0.0071 (4)	0.0010 (4)
C6	0.0171 (4)	0.0135 (4)	0.0177 (4)	0.0043 (3)	0.0054 (4)	0.0023 (3)
C7	0.0156 (4)	0.0130 (4)	0.0186 (4)	0.0034 (3)	0.0059 (3)	0.0023 (3)
C8	0.0140 (4)	0.0114 (4)	0.0179 (4)	0.0019 (3)	0.0054 (3)	0.0021 (3)
C9	0.0155 (4)	0.0121 (4)	0.0181 (4)	0.0025 (3)	0.0046 (3)	0.0019 (3)
C10	0.0155 (4)	0.0131 (4)	0.0175 (4)	0.0033 (3)	0.0042 (3)	0.0005 (3)
C11	0.0158 (4)	0.0169 (4)	0.0212 (5)	0.0025 (4)	0.0064 (4)	0.0017 (4)
C12	0.0169 (5)	0.0161 (4)	0.0246 (5)	0.0019 (4)	0.0089 (4)	0.0045 (4)
C13	0.0162 (4)	0.0136 (4)	0.0191 (4)	0.0033 (3)	0.0064 (4)	0.0032 (3)
C14	0.0170 (5)	0.0149 (4)	0.0189 (4)	0.0040 (3)	0.0034 (4)	0.0007 (3)
C15	0.0283 (6)	0.0170 (5)	0.0334 (6)	0.0121 (4)	0.0118 (5)	0.0070 (4)
C16	0.0335 (7)	0.0215 (6)	0.0440 (8)	0.0110 (5)	0.0171 (6)	0.0111 (6)
C17A	0.0178 (6)	0.0125 (5)	0.0212 (6)	0.0013 (4)	0.0039 (5)	0.0058 (5)
C18A	0.0219 (7)	0.0279 (7)	0.0197 (6)	0.0051 (6)	0.0064 (5)	0.0090 (5)
C19A	0.0267 (8)	0.0356 (9)	0.0180 (6)	0.0097 (7)	0.0016 (5)	−0.0007 (6)
C20A	0.0229 (7)	0.0157 (6)	0.0456 (11)	−0.0037 (5)	0.0083 (7)	0.0041 (6)

Geometric parameters (Å, º) top

Cl1—C3	1.7332 (12)	C15—C16	1.503 (2)
O1—C14	1.3433 (15)	C15—H15A	0.9700
O1—C15	1.4486 (15)	C15—H15B	0.9700
O2—C14	1.2131 (15)	C16—H16A	0.9600
N1—C7	1.3240 (14)	C16—H16B	0.9600
N1—C8	1.3854 (14)	C16—H16C	0.9600
N2—C7	1.3828 (15)	C17A—C18A	1.527 (2)
N2—C13	1.3879 (14)	C17A—C20A	1.530 (2)
N2—C17A	1.4769 (16)	C17A—H17A	0.9800
N2—C17B	1.595 (9)	C18A—C19A	1.518 (3)
C1—C2	1.3897 (17)	C18A—H18A	0.9700
C1—C6	1.3998 (16)	C18A—H18B	0.9700
C1—H1A	0.9300	C19A—H19A	0.9600
C2—C3	1.3812 (19)	C19A—H19B	0.9600
C2—H2A	0.9300	C19A—H19C	0.9600
C3—C4	1.3879 (18)	C20A—H20A	0.9600
C4—C5	1.3895 (17)	C20A—H20B	0.9600
C4—H4A	0.9300	C20A—H20C	0.9600
C5—C6	1.3960 (17)	C17B—C20B	1.447 (15)
C5—H5A	0.9300	C17B—C18B	1.508 (15)
C6—C7	1.4725 (15)	C17B—H17B	0.9800
C8—C9	1.3956 (15)	C18B—C19B	1.576 (18)
C8—C13	1.4112 (15)	C18B—H18C	0.9700
C9—C10	1.3881 (16)	C18B—H18D	0.9700
C9—H9A	0.9300	C19B—H19D	0.9600
C10—C11	1.4104 (16)	C19B—H19E	0.9600
C10—C14	1.4854 (15)	C19B—H19F	0.9600
C11—C12	1.3863 (16)	C20B—H20D	0.9600
C11—H11A	0.9300	C20B—H20E	0.9600
C12—C13	1.3998 (16)	C20B—H20F	0.9600
C12—H12A	0.9300

C14—O1—C15	116.59 (10)	O1—C15—C16	106.49 (11)
C7—N1—C8	104.38 (9)	O1—C15—H15A	110.4
C7—N2—C13	105.87 (9)	C16—C15—H15A	110.4
C7—N2—C17A	126.20 (10)	O1—C15—H15B	110.4
C13—N2—C17A	125.61 (10)	C16—C15—H15B	110.4
C7—N2—C17B	116.8 (4)	H15A—C15—H15B	108.6
C13—N2—C17B	123.2 (3)	C15—C16—H16A	109.5
C2—C1—C6	120.43 (12)	C15—C16—H16B	109.5
C2—C1—H1A	119.8	H16A—C16—H16B	109.5
C6—C1—H1A	119.8	C15—C16—H16C	109.5
C3—C2—C1	119.14 (11)	H16A—C16—H16C	109.5
C3—C2—H2A	120.4	H16B—C16—H16C	109.5
C1—C2—H2A	120.4	N2—C17A—C18A	109.21 (12)
C2—C3—C4	121.67 (11)	N2—C17A—C20A	112.67 (14)
C2—C3—Cl1	119.06 (10)	C18A—C17A—C20A	113.35 (13)
C4—C3—Cl1	119.26 (10)	N2—C17A—H17A	107.1
C3—C4—C5	118.92 (12)	C18A—C17A—H17A	107.1
C3—C4—H4A	120.5	C20A—C17A—H17A	107.1
C5—C4—H4A	120.5	C19A—C18A—C17A	112.15 (12)
C4—C5—C6	120.60 (11)	C19A—C18A—H18A	109.2
C4—C5—H5A	119.7	C17A—C18A—H18A	109.2
C6—C5—H5A	119.7	C19A—C18A—H18B	109.2
C5—C6—C1	119.22 (10)	C17A—C18A—H18B	109.2
C5—C6—C7	118.75 (10)	H18A—C18A—H18B	107.9
C1—C6—C7	121.88 (11)	C20B—C17B—C18B	111.2 (9)
N1—C7—N2	113.76 (9)	C20B—C17B—N2	118.1 (8)
N1—C7—C6	122.25 (10)	C18B—C17B—N2	103.4 (8)
N2—C7—C6	123.86 (10)	C20B—C17B—H17B	107.9
N1—C8—C9	128.88 (10)	C18B—C17B—H17B	107.9
N1—C8—C13	110.60 (9)	N2—C17B—H17B	107.9
C9—C8—C13	120.52 (10)	C17B—C18B—C19B	116.0 (9)
C10—C9—C8	117.80 (10)	C17B—C18B—H18C	108.3
C10—C9—H9A	121.1	C19B—C18B—H18C	108.3
C8—C9—H9A	121.1	C17B—C18B—H18D	108.3
C9—C10—C11	121.19 (10)	C19B—C18B—H18D	108.3
C9—C10—C14	120.64 (10)	H18C—C18B—H18D	107.4
C11—C10—C14	118.17 (10)	C18B—C19B—H19D	109.5
C12—C11—C10	121.83 (10)	C18B—C19B—H19E	109.5
C12—C11—H11A	119.1	H19D—C19B—H19E	109.5
C10—C11—H11A	119.1	C18B—C19B—H19F	109.5
C11—C12—C13	116.72 (10)	H19D—C19B—H19F	109.5
C11—C12—H12A	121.6	H19E—C19B—H19F	109.5
C13—C12—H12A	121.6	C17B—C20B—H20D	109.5
N2—C13—C12	132.68 (10)	C17B—C20B—H20E	109.5
N2—C13—C8	105.39 (9)	H20D—C20B—H20E	109.5
C12—C13—C8	121.93 (10)	C17B—C20B—H20F	109.5
O2—C14—O1	123.27 (11)	H20D—C20B—H20F	109.5
O2—C14—C10	124.96 (11)	H20E—C20B—H20F	109.5
O1—C14—C10	111.77 (10)

C6—C1—C2—C3	−0.27 (18)	C17B—N2—C13—C12	−41.3 (5)
C1—C2—C3—C4	0.76 (19)	C7—N2—C13—C8	0.12 (13)
C1—C2—C3—Cl1	−178.33 (9)	C17A—N2—C13—C8	163.64 (13)
C2—C3—C4—C5	−0.55 (19)	C17B—N2—C13—C8	138.5 (5)
Cl1—C3—C4—C5	178.54 (10)	C11—C12—C13—N2	179.91 (13)
C3—C4—C5—C6	−0.15 (19)	C11—C12—C13—C8	0.17 (18)
C4—C5—C6—C1	0.63 (18)	N1—C8—C13—N2	−0.11 (13)
C4—C5—C6—C7	−174.93 (11)	C9—C8—C13—N2	179.26 (10)
C2—C1—C6—C5	−0.42 (17)	N1—C8—C13—C12	179.69 (11)
C2—C1—C6—C7	175.00 (11)	C9—C8—C13—C12	−0.94 (18)
C8—N1—C7—N2	0.02 (14)	C15—O1—C14—O2	0.54 (19)
C8—N1—C7—C6	176.15 (11)	C15—O1—C14—C10	179.96 (11)
C13—N2—C7—N1	−0.09 (14)	C9—C10—C14—O2	−176.84 (12)
C17A—N2—C7—N1	−163.48 (13)	C11—C10—C14—O2	2.36 (19)
C17B—N2—C7—N1	−141.6 (4)	C9—C10—C14—O1	3.75 (16)
C13—N2—C7—C6	−176.15 (11)	C11—C10—C14—O1	−177.05 (11)
C17A—N2—C7—C6	20.5 (2)	C14—O1—C15—C16	−168.74 (13)
C17B—N2—C7—C6	42.4 (5)	C7—N2—C17A—C18A	108.23 (14)
C5—C6—C7—N1	38.83 (17)	C13—N2—C17A—C18A	−52.01 (18)
C1—C6—C7—N1	−136.61 (12)	C17B—N2—C17A—C18A	38.7 (9)
C5—C6—C7—N2	−145.43 (12)	C7—N2—C17A—C20A	−124.87 (14)
C1—C6—C7—N2	39.13 (17)	C13—N2—C17A—C20A	74.90 (18)
C7—N1—C8—C9	−179.25 (12)	C17B—N2—C17A—C20A	165.6 (10)
C7—N1—C8—C13	0.06 (13)	N2—C17A—C18A—C19A	−50.27 (16)
N1—C8—C9—C10	−179.71 (11)	C20A—C17A—C18A—C19A	−176.79 (13)
C13—C8—C9—C10	1.04 (17)	C7—N2—C17B—C20B	92.8 (8)
C8—C9—C10—C11	−0.44 (17)	C13—N2—C17B—C20B	−41.5 (10)
C8—C9—C10—C14	178.73 (10)	C17A—N2—C17B—C20B	−145.1 (15)
C9—C10—C11—C12	−0.32 (18)	C7—N2—C17B—C18B	−144.0 (5)
C14—C10—C11—C12	−179.51 (11)	C13—N2—C17B—C18B	81.8 (7)
C10—C11—C12—C13	0.44 (18)	C17A—N2—C17B—C18B	−21.9 (7)
C7—N2—C13—C12	−179.65 (13)	C20B—C17B—C18B—C19B	−178.0 (9)
C17A—N2—C13—C12	−16.1 (2)	N2—C17B—C18B—C19B	54.3 (10)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1/C7/N2/C13/C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O2ⁱ	0.93	2.57	3.4994 (16)	174
C16—H16A···Cl1ⁱⁱ	0.96	2.73	3.4651 (17)	134
C19A—H19B···Cg1	0.96	2.71	3.3457 (18)	124

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

Experimental details

Crystal data
Chemical formula	C₂₀H₂₁ClN₂O₂
M_r	356.84
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.4321 (9), 12.6218 (12), 13.6896 (12)
β (°)	97.043 (3)
V (Å³)	1788.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.45 × 0.34 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.904, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	21234, 8437, 6651
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.830

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.175, 1.09
No. of reflections	8437
No. of parameters	248
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.75, −0.39

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/C13/C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O2ⁱ	0.93	2.57	3.4994 (16)	174
C16—H16A···Cl1ⁱⁱ	0.96	2.73	3.4651 (17)	134
C19A—H19B···Cg1	0.96	2.71	3.3457 (18)	124

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

Footnotes

‡Additional correspondence author, e-mail: aisyah@usm.my.

§Thomson Reuters ResearcherID: A-5525-2009.

¶Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

NA, ASAR and HO acknowledge Universiti Sains Malaysia (USM) for funding the synthetic chemistry work under Research University Grant No. 1001/PFARMASI/815026 and MOSTI Grant 304/PFARMASI/650512/I121. HKF and CKQ thank USM for the Research University Grant No. 1001/PFIZIK/811160 for funding the crystallography work done in this article. NA also thanks USM for the award of a postdoctoral fellowship. CKQ also thanks USM for the award of a research fellowship.

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